MiMeDB: Showing metabocard for trans-Isohumulone (MMDBc0033722)

Record Information

Version

2.0

Status

Detected and Quantified

Creation Date

2021-11-19 05:00:27 UTC

Update Date

2025-10-07 16:08:03 UTC

Metabolite ID

MMDBc0033722

Metabolite Identification

Common Name

trans-Isohumulone

Description

trans-Isohumulone is a member of the chemical class of iso-alpha acids, which are derived from the hops plant (Humulus lupulus) and are known for their role in brewing. Its chemical structure features a unique arrangement of isoprenoid chains and functional groups that contribute to its reactivity and biological activity. In biochemical pathways, trans-Isohumulone is involved in various transformations, such as the formation of carboxylic acids and proline amides when incubated with l-proline (PMID:25026227 ). It participates in oxidative reactions, leading to the production of hydroperoxy- and hydroxyl-allo-iso-alpha-acids, which have been characterized using advanced NMR and chromatography techniques (PMID:17624889 ). Additionally, trans-Isohumulone has been shown to induce the production of fructan and fructose-oligosaccharides in certain bacterial strains, enhancing transcription of genes related to these pathways under specific conditions (PMID:16464690 ). Its antibacterial properties are notable, exhibiting significantly greater activity compared to related compounds, which is influenced by the presence of monovalent cations (PMID:1517174 ). Furthermore, trans-Isohumulone undergoes photochemical transformations, leading to new derivatives, thereby highlighting its complex chemistry and potential applications (PMID:32027492 ).

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 02241223262D          

 26 26  0  0  1  0            999 V2000
   -0.1435   -2.9975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4790   -2.2438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2995   -2.1576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0059   -1.5764    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3297   -0.8227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1501   -0.7365    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1553   -0.1553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0997    0.6294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    1.1143    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2352    0.6294    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9803   -0.1553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4652   -0.8227    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0198    0.8843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6329    0.3323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4175    0.5872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0306    0.0352    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5891    1.3942    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1628    1.8330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6622    1.8417    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5827    2.5432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1777    3.2619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5977    3.9720    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1927    4.6908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4226    3.9634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9728    1.8330    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8843    0.8843    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
  7 11  1  0  0  0  0
 11 12  2  0  0  0  0
 10 13  1  6  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 15 17  1  0  0  0  0
  9 18  1  6  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 22 24  1  0  0  0  0
  9 25  1  1  0  0  0
  8 26  1  0  0  0  0
M  END


  Mrv0541 02241223262D          

 26 26  0  0  1  0            999 V2000
   -0.1435   -2.9975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4790   -2.2438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2995   -2.1576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0059   -1.5764    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3297   -0.8227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1501   -0.7365    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1553   -0.1553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0997    0.6294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    1.1143    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2352    0.6294    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9803   -0.1553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4652   -0.8227    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0198    0.8843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6329    0.3323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4175    0.5872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0306    0.0352    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5891    1.3942    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1628    1.8330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6622    1.8417    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5827    2.5432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1777    3.2619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5977    3.9720    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1927    4.6908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4226    3.9634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9728    1.8330    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8843    0.8843    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
  7 11  1  0  0  0  0
 11 12  2  0  0  0  0
 10 13  1  6  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 15 17  1  0  0  0  0
  9 18  1  6  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 22 24  1  0  0  0  0
  9 25  1  1  0  0  0
  8 26  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0033722

> <DATABASE_NAME>
MIME

> <SMILES>
CC(C)CC(=O)C1=C(O)[C@@](O)([C@H](CC=C(C)C)C1=O)C(=O)CC=C(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C21H30O5/c1-12(2)7-9-15-19(24)18(16(22)11-14(5)6)20(25)21(15,26)17(23)10-8-13(3)4/h7-8,14-15,25-26H,9-11H2,1-6H3/t15-,21-/m1/s1

> <INCHI_KEY>
QARXXMMQVDCYGZ-QVKFZJNVSA-N

> <FORMULA>
C21H30O5

> <MOLECULAR_WEIGHT>
362.4599

> <EXACT_MASS>
362.20932407

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
40.15239722442915

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(4S,5S)-3,4-dihydroxy-5-(3-methylbut-2-en-1-yl)-2-(3-methylbutanoyl)-4-(4-methylpent-3-enoyl)cyclopent-2-en-1-one

> <ALOGPS_LOGP>
2.49

> <JCHEM_LOGP>
3.9096914630000006

> <ALOGPS_LOGS>
-3.70

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
11.88975276214697

> <JCHEM_PKA_STRONGEST_ACIDIC>
0.5622788019661003

> <JCHEM_PKA_STRONGEST_BASIC>
-4.370488344465941

> <JCHEM_POLAR_SURFACE_AREA>
91.67

> <JCHEM_REFRACTIVITY>
104.07449999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.25e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(4S,5S)-3,4-dihydroxy-5-(3-methylbut-2-en-1-yl)-2-(3-methylbutanoyl)-4-(4-methylpent-3-enoyl)cyclopent-2-en-1-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      -0.268  -5.595   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.894  -4.188   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.426  -4.028   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.011  -2.943   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.615  -1.536   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      -2.147  -1.375   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       0.290  -0.290   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.186   1.175   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.060   2.080   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.306   1.175   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.830  -0.290   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       2.735  -1.536   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       3.770   1.651   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.915   0.620   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.379   1.096   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       7.524   0.066   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.700   2.603   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.304   3.422   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -1.236   3.438   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       1.088   4.747   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       0.332   6.089   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       1.116   7.414   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       0.360   8.756   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       2.656   7.398   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       1.816   3.422   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0      -1.651   1.651   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8   11                                                  
CONECT    8    7    9   26                                                  
CONECT    9    8   10   18   25                                             
CONECT   10    9   11   13                                                  
CONECT   11   10    7   12                                                  
CONECT   12   11                                                            
CONECT   13   10   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15                                                            
CONECT   18    9   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22                                                            
CONECT   25    9                                                            
CONECT   26    8                                                            
MASTER        0    0    0    0    0    0    0    0   26    0   52    0
END

Synonyms

Not Available

Molecular Formula

C₂₁H₃₀O₅

Average Mass

362.4599

Monoisotopic Mass

362.20932407

IUPAC Name

(4S,5S)-3,4-dihydroxy-5-(3-methylbut-2-en-1-yl)-2-(3-methylbutanoyl)-4-(4-methylpent-3-enoyl)cyclopent-2-en-1-one

Traditional Name

(4S,5S)-3,4-dihydroxy-5-(3-methylbut-2-en-1-yl)-2-(3-methylbutanoyl)-4-(4-methylpent-3-enoyl)cyclopent-2-en-1-one

CAS Registry Number

Not Available

SMILES

CC(C)CC(=O)C1=C(O)[C@@](O)([C@H](CC=C(C)C)C1=O)C(=O)CC=C(C)C

InChI Identifier

InChI=1S/C21H30O5/c1-12(2)7-9-15-19(24)18(16(22)11-14(5)6)20(25)21(15,26)17(23)10-8-13(3)4/h7-8,14-15,25-26H,9-11H2,1-6H3/t15-,21-/m1/s1

InChI Key

QARXXMMQVDCYGZ-QVKFZJNVSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as monocyclic monoterpenoids. These are monoterpenoids containing 1 ring in the isoprene chain.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Monoterpenoids

Direct Parent

Monocyclic monoterpenoids

Alternative Parents

Substituents

Monocyclic monoterpenoid
Vinylogous acid
Tertiary alcohol
Alpha-hydroxy ketone
Cyclic ketone
Ketone
Enol
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	0.072 g/L	ALOGPS
logP	2.49	ALOGPS
logP	3.91	ChemAxon
logS	-3.7	ALOGPS
pKa (Strongest Acidic)	0.56	ChemAxon
pKa (Strongest Basic)	-4.4	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	91.67 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	104.07 m³·mol⁻¹	ChemAxon
Polarizability	40.15 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_4_5) - 70eV, Positive	Not Available	2022-08-08	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03di-1029000000-a36c0509d5def9324024	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-052b-8096000000-0a217511ea67b9e1e650	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a59-9340000000-9e9b9fb4e235c6f18fa9	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03di-1049000000-39c7238bec6f61470f45	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-002b-9174000000-1c6b3c57c4135dba3508	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a5a-9570000000-7a34e36a8c4ae7aa96d1	2016-09-12	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-23	View Spectrum

Chromatographic Retention Times and Retention Indices

Retention Times

Chromatography Type	Technique	Column	Deposition Date	Retention Time (s)
Liquid Chromatography	HILIC	Waters Acquity UPLC-BEH Amide column (eluted)	2025-10-24	37.6
Liquid Chromatography	HILIC	Accucore 150 Amide HILIC (void)	2025-10-24	27.4
Liquid Chromatography	Reversed-phase	Hypersil Gold 1.9 µm C18 (eluted)	2025-10-24	552.8
Liquid Chromatography	Reversed-phase	Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) (eluted)	2025-10-24	596.2
Liquid Chromatography	Reversed-phase	XBridge C18 3.5u 2.1x50 mm (eluted)	2025-10-24	697.7
Liquid Chromatography	Reversed-phase	Ascentis Express C18 (eluted)	2025-10-24	246.7
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-24	2931.6
Liquid Chromatography	HILIC	Merck SeQuant ZIC-HILIC (void)	2025-10-24	74.0
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC (eluted)	2025-10-24	315.3
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-24	523.1
Liquid Chromatography	HILIC	Merck SeQuant ZIC-HILIC (eluted)	2025-10-24	180.6
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-24	149.8
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-24	181.0
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC column (eluted)	2025-10-24	8.2
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC column (eluted)	2025-10-24	131.7
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-24	84.6
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-24	459.9
Liquid Chromatography	Reversed-phase	Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex (eluted)	2025-10-24	1367.4
Liquid Chromatography	Reversed-phase	Waters Atlantis T3 (2.1 x 150 mm, 5 um) (eluted)	2025-10-24	1122.3

Retention Indices

Chromatography Type	Peak Label	SMILES	Stationary Phase	Deposition Date	Retention Index
Gas Chromatography	trans-Isohumulone_TMS_1	CC(C)=CCC(=O)[C@@]1(O)C(O[Si](C)(C)C)=C(C(=O)CC(C)C)C(=O)[C@H]1CC=C(C)C	standard non polar	2025-10-24	2194.71
Gas Chromatography	trans-Isohumulone_TMS_2	CC(C)=CCC(=O)[C@@]1(O[Si](C)(C)C)C(O)=C(C(=O)CC(C)C)C(=O)[C@H]1CC=C(C)C	standard non polar	2025-10-24	955.272
Gas Chromatography	trans-Isohumulone_TMS_3	CC(C)=CCC(=O)[C@@]1(O)C(O)=C(C(=O)CC(C)C)C(O[Si](C)(C)C)=C1CC=C(C)C	standard non polar	2025-10-24	2053.74
Gas Chromatography	trans-Isohumulone_TMS_4	CC(C)=CCC(=O)[C@@]1(O)C(O)=C(C(=CC(C)C)O[Si](C)(C)C)C(=O)[C@H]1CC=C(C)C	standard non polar	2025-10-24	2335.28
Gas Chromatography	trans-Isohumulone_TMS_5	CC(C)=CC=C(O[Si](C)(C)C)[C@@]1(O)C(O)=C(C(=O)CC(C)C)C(=O)[C@H]1CC=C(C)C	standard non polar	2025-10-24	1660.35
Gas Chromatography	trans-Isohumulone_TMS_6	CC(C)=CCC(=O)[C@@]1(O[Si](C)(C)C)C(O[Si](C)(C)C)=C(C(=O)CC(C)C)C(=O)[C@H]1CC=C(C)C	standard non polar	2025-10-24	2301.92
Gas Chromatography	trans-Isohumulone_TMS_7	CC(C)=CCC(=O)[C@]1(O)C(CC=C(C)C)=C(O[Si](C)(C)C)C(C(=O)CC(C)C)=C1O[Si](C)(C)C	standard non polar	2025-10-24	3145.47
Gas Chromatography	trans-Isohumulone_TMS_8	CC(C)=CC=C(O[Si](C)(C)C)[C@@]1(O)C(O[Si](C)(C)C)=C(C(=O)CC(C)C)C(=O)[C@H]1CC=C(C)C	standard non polar	2025-10-24	1062.12
Gas Chromatography	trans-Isohumulone_TMS_9	CC(C)=CCC(=O)[C@@]1(O)C(O[Si](C)(C)C)=C(C(=CC(C)C)O[Si](C)(C)C)C(=O)[C@H]1CC=C(C)C	standard non polar	2025-10-24	2550.74
Gas Chromatography	trans-Isohumulone_TMS_10	CC(C)=CCC(=O)[C@@]1(O[Si](C)(C)C)C(O)=C(C(=O)CC(C)C)C(O[Si](C)(C)C)=C1CC=C(C)C	standard non polar	2025-10-24	2114.79
Gas Chromatography	trans-Isohumulone_TMS_11	CC(C)=CC=C(O[Si](C)(C)C)[C@@]1(O[Si](C)(C)C)C(O)=C(C(=O)CC(C)C)C(=O)[C@H]1CC=C(C)C	standard non polar	2025-10-24	2208.96
Gas Chromatography	trans-Isohumulone_TMS_12	CC(C)=CCC(=O)[C@@]1(O[Si](C)(C)C)C(O)=C(C(=CC(C)C)O[Si](C)(C)C)C(=O)[C@H]1CC=C(C)C	standard non polar	2025-10-24	1879.03
Gas Chromatography	trans-Isohumulone_TMS_13	CC(C)=CC=C(O[Si](C)(C)C)[C@@]1(O)C(O)=C(C(=O)CC(C)C)C(O[Si](C)(C)C)=C1CC=C(C)C	standard non polar	2025-10-24	1884.11
Gas Chromatography	trans-Isohumulone_TMS_14	CC(C)=CCC(=O)[C@@]1(O)C(O)=C(C(=CC(C)C)O[Si](C)(C)C)C(O[Si](C)(C)C)=C1CC=C(C)C	standard non polar	2025-10-24	2246.42
Gas Chromatography	trans-Isohumulone_TMS_15	CC(C)=CC=C(O[Si](C)(C)C)[C@@]1(O)C(O)=C(C(=CC(C)C)O[Si](C)(C)C)C(=O)[C@H]1CC=C(C)C	standard non polar	2025-10-24	1870.69
Gas Chromatography	trans-Isohumulone_TMS_16	CC(C)=CCC(=O)[C@]1(O[Si](C)(C)C)C(CC=C(C)C)=C(O[Si](C)(C)C)C(C(=O)CC(C)C)=C1O[Si](C)(C)C	standard non polar	2025-10-24	2328.52
Gas Chromatography	trans-Isohumulone_TMS_17	CC(C)=CC=C(O[Si](C)(C)C)[C@@]1(O[Si](C)(C)C)C(O[Si](C)(C)C)=C(C(=O)CC(C)C)C(=O)[C@H]1CC=C(C)C	standard non polar	2025-10-24	1036.71
Gas Chromatography	trans-Isohumulone_TMS_18	CC(C)=CCC(=O)[C@@]1(O[Si](C)(C)C)C(O[Si](C)(C)C)=C(C(=CC(C)C)O[Si](C)(C)C)C(=O)[C@H]1CC=C(C)C	standard non polar	2025-10-24	2846.48
Gas Chromatography	trans-Isohumulone_TMS_19	CC(C)=CC=C(O[Si](C)(C)C)[C@]1(O)C(CC=C(C)C)=C(O[Si](C)(C)C)C(C(=O)CC(C)C)=C1O[Si](C)(C)C	standard non polar	2025-10-24	1342.09
Gas Chromatography	trans-Isohumulone_TMS_20	CC(C)=CCC(=O)[C@]1(O)C(CC=C(C)C)=C(O[Si](C)(C)C)C(C(=CC(C)C)O[Si](C)(C)C)=C1O[Si](C)(C)C	standard non polar	2025-10-24	2756.14
Gas Chromatography	trans-Isohumulone_TMS_21	CC(C)=CC=C(O[Si](C)(C)C)[C@@]1(O)C(O[Si](C)(C)C)=C(C(=CC(C)C)O[Si](C)(C)C)C(=O)[C@H]1CC=C(C)C	standard non polar	2025-10-24	1700.51
Gas Chromatography	trans-Isohumulone_TMS_22	CC(C)=CC=C(O[Si](C)(C)C)[C@@]1(O[Si](C)(C)C)C(O)=C(C(=O)CC(C)C)C(O[Si](C)(C)C)=C1CC=C(C)C	standard non polar	2025-10-24	1817.93
Gas Chromatography	trans-Isohumulone_TMS_23	CC(C)=CCC(=O)[C@@]1(O[Si](C)(C)C)C(O)=C(C(=CC(C)C)O[Si](C)(C)C)C(O[Si](C)(C)C)=C1CC=C(C)C	standard non polar	2025-10-24	2643.06
Gas Chromatography	trans-Isohumulone_TMS_24	CC(C)=CC=C(O[Si](C)(C)C)[C@@]1(O[Si](C)(C)C)C(O)=C(C(=CC(C)C)O[Si](C)(C)C)C(=O)[C@H]1CC=C(C)C	standard non polar	2025-10-24	1933.38
Gas Chromatography	trans-Isohumulone_TMS_25	CC(C)=CC=C(O[Si](C)(C)C)[C@@]1(O)C(O)=C(C(=CC(C)C)O[Si](C)(C)C)C(O[Si](C)(C)C)=C1CC=C(C)C	standard non polar	2025-10-24	2792.0
Gas Chromatography	trans-Isohumulone_TMS_26	CC(C)=CC=C(O[Si](C)(C)C)[C@]1(O[Si](C)(C)C)C(CC=C(C)C)=C(O[Si](C)(C)C)C(C(=O)CC(C)C)=C1O[Si](C)(C)C	standard non polar	2025-10-24	2883.37
Gas Chromatography	trans-Isohumulone_TMS_27	CC(C)=CCC(=O)[C@]1(O[Si](C)(C)C)C(CC=C(C)C)=C(O[Si](C)(C)C)C(C(=CC(C)C)O[Si](C)(C)C)=C1O[Si](C)(C)C	standard non polar	2025-10-24	1536.56
Gas Chromatography	trans-Isohumulone_TMS_28	CC(C)=CC=C(O[Si](C)(C)C)[C@@]1(O[Si](C)(C)C)C(O[Si](C)(C)C)=C(C(=CC(C)C)O[Si](C)(C)C)C(=O)[C@H]1CC=C(C)C	standard non polar	2025-10-24	2590.05
Gas Chromatography	trans-Isohumulone_TMS_29	CC(C)=CC=C(O[Si](C)(C)C)[C@]1(O)C(CC=C(C)C)=C(O[Si](C)(C)C)C(C(=CC(C)C)O[Si](C)(C)C)=C1O[Si](C)(C)C	standard non polar	2025-10-24	2177.61
Gas Chromatography	trans-Isohumulone_TMS_30	CC(C)=CC=C(O[Si](C)(C)C)[C@@]1(O[Si](C)(C)C)C(O)=C(C(=CC(C)C)O[Si](C)(C)C)C(O[Si](C)(C)C)=C1CC=C(C)C	standard non polar	2025-10-24	1964.64
Gas Chromatography	trans-Isohumulone_TMS_31	CC(C)=CC=C(O[Si](C)(C)C)[C@]1(O[Si](C)(C)C)C(CC=C(C)C)=C(O[Si](C)(C)C)C(C(=CC(C)C)O[Si](C)(C)C)=C1O[Si](C)(C)C	standard non polar	2025-10-24	2409.71
Gas Chromatography	trans-Isohumulone_TMS_1	CC(C)=CCC(=O)[C@@]1(O)C(O[Si](C)(C)C)=C(C(=O)CC(C)C)C(=O)[C@H]1CC=C(C)C	standard polar	2025-10-24	2086.48
Gas Chromatography	trans-Isohumulone_TMS_2	CC(C)=CCC(=O)[C@@]1(O[Si](C)(C)C)C(O)=C(C(=O)CC(C)C)C(=O)[C@H]1CC=C(C)C	standard polar	2025-10-24	2291.87
Gas Chromatography	trans-Isohumulone_TMS_3	CC(C)=CCC(=O)[C@@]1(O)C(O)=C(C(=O)CC(C)C)C(O[Si](C)(C)C)=C1CC=C(C)C	standard polar	2025-10-24	1494.6
Gas Chromatography	trans-Isohumulone_TMS_4	CC(C)=CCC(=O)[C@@]1(O)C(O)=C(C(=CC(C)C)O[Si](C)(C)C)C(=O)[C@H]1CC=C(C)C	standard polar	2025-10-24	2808.85
Gas Chromatography	trans-Isohumulone_TMS_5	CC(C)=CC=C(O[Si](C)(C)C)[C@@]1(O)C(O)=C(C(=O)CC(C)C)C(=O)[C@H]1CC=C(C)C	standard polar	2025-10-24	1729.78
Gas Chromatography	trans-Isohumulone_TMS_6	CC(C)=CCC(=O)[C@@]1(O[Si](C)(C)C)C(O[Si](C)(C)C)=C(C(=O)CC(C)C)C(=O)[C@H]1CC=C(C)C	standard polar	2025-10-24	3105.71
Gas Chromatography	trans-Isohumulone_TMS_7	CC(C)=CCC(=O)[C@]1(O)C(CC=C(C)C)=C(O[Si](C)(C)C)C(C(=O)CC(C)C)=C1O[Si](C)(C)C	standard polar	2025-10-24	2249.08
Gas Chromatography	trans-Isohumulone_TMS_8	CC(C)=CC=C(O[Si](C)(C)C)[C@@]1(O)C(O[Si](C)(C)C)=C(C(=O)CC(C)C)C(=O)[C@H]1CC=C(C)C	standard polar	2025-10-24	2484.28
Gas Chromatography	trans-Isohumulone_TMS_9	CC(C)=CCC(=O)[C@@]1(O)C(O[Si](C)(C)C)=C(C(=CC(C)C)O[Si](C)(C)C)C(=O)[C@H]1CC=C(C)C	standard polar	2025-10-24	1706.25
Gas Chromatography	trans-Isohumulone_TMS_10	CC(C)=CCC(=O)[C@@]1(O[Si](C)(C)C)C(O)=C(C(=O)CC(C)C)C(O[Si](C)(C)C)=C1CC=C(C)C	standard polar	2025-10-24	2859.24
Gas Chromatography	trans-Isohumulone_TMS_11	CC(C)=CC=C(O[Si](C)(C)C)[C@@]1(O[Si](C)(C)C)C(O)=C(C(=O)CC(C)C)C(=O)[C@H]1CC=C(C)C	standard polar	2025-10-24	2937.49
Gas Chromatography	trans-Isohumulone_TMS_12	CC(C)=CCC(=O)[C@@]1(O[Si](C)(C)C)C(O)=C(C(=CC(C)C)O[Si](C)(C)C)C(=O)[C@H]1CC=C(C)C	standard polar	2025-10-24	1001.61
Gas Chromatography	trans-Isohumulone_TMS_13	CC(C)=CC=C(O[Si](C)(C)C)[C@@]1(O)C(O)=C(C(=O)CC(C)C)C(O[Si](C)(C)C)=C1CC=C(C)C	standard polar	2025-10-24	2172.34
Gas Chromatography	trans-Isohumulone_TMS_14	CC(C)=CCC(=O)[C@@]1(O)C(O)=C(C(=CC(C)C)O[Si](C)(C)C)C(O[Si](C)(C)C)=C1CC=C(C)C	standard polar	2025-10-24	2490.04
Gas Chromatography	trans-Isohumulone_TMS_15	CC(C)=CC=C(O[Si](C)(C)C)[C@@]1(O)C(O)=C(C(=CC(C)C)O[Si](C)(C)C)C(=O)[C@H]1CC=C(C)C	standard polar	2025-10-24	2559.59
Gas Chromatography	trans-Isohumulone_TMS_16	CC(C)=CCC(=O)[C@]1(O[Si](C)(C)C)C(CC=C(C)C)=C(O[Si](C)(C)C)C(C(=O)CC(C)C)=C1O[Si](C)(C)C	standard polar	2025-10-24	2828.82
Gas Chromatography	trans-Isohumulone_TMS_17	CC(C)=CC=C(O[Si](C)(C)C)[C@@]1(O[Si](C)(C)C)C(O[Si](C)(C)C)=C(C(=O)CC(C)C)C(=O)[C@H]1CC=C(C)C	standard polar	2025-10-24	2909.85
Gas Chromatography	trans-Isohumulone_TMS_18	CC(C)=CCC(=O)[C@@]1(O[Si](C)(C)C)C(O[Si](C)(C)C)=C(C(=CC(C)C)O[Si](C)(C)C)C(=O)[C@H]1CC=C(C)C	standard polar	2025-10-24	2475.75
Gas Chromatography	trans-Isohumulone_TMS_19	CC(C)=CC=C(O[Si](C)(C)C)[C@]1(O)C(CC=C(C)C)=C(O[Si](C)(C)C)C(C(=O)CC(C)C)=C1O[Si](C)(C)C	standard polar	2025-10-24	1589.45
Gas Chromatography	trans-Isohumulone_TMS_20	CC(C)=CCC(=O)[C@]1(O)C(CC=C(C)C)=C(O[Si](C)(C)C)C(C(=CC(C)C)O[Si](C)(C)C)=C1O[Si](C)(C)C	standard polar	2025-10-24	1876.32
Gas Chromatography	trans-Isohumulone_TMS_21	CC(C)=CC=C(O[Si](C)(C)C)[C@@]1(O)C(O[Si](C)(C)C)=C(C(=CC(C)C)O[Si](C)(C)C)C(=O)[C@H]1CC=C(C)C	standard polar	2025-10-24	1296.76
Gas Chromatography	trans-Isohumulone_TMS_22	CC(C)=CC=C(O[Si](C)(C)C)[C@@]1(O[Si](C)(C)C)C(O)=C(C(=O)CC(C)C)C(O[Si](C)(C)C)=C1CC=C(C)C	standard polar	2025-10-24	2008.2
Gas Chromatography	trans-Isohumulone_TMS_23	CC(C)=CCC(=O)[C@@]1(O[Si](C)(C)C)C(O)=C(C(=CC(C)C)O[Si](C)(C)C)C(O[Si](C)(C)C)=C1CC=C(C)C	standard polar	2025-10-24	2406.56
Gas Chromatography	trans-Isohumulone_TMS_24	CC(C)=CC=C(O[Si](C)(C)C)[C@@]1(O[Si](C)(C)C)C(O)=C(C(=CC(C)C)O[Si](C)(C)C)C(=O)[C@H]1CC=C(C)C	standard polar	2025-10-24	3066.89
Gas Chromatography	trans-Isohumulone_TMS_25	CC(C)=CC=C(O[Si](C)(C)C)[C@@]1(O)C(O)=C(C(=CC(C)C)O[Si](C)(C)C)C(O[Si](C)(C)C)=C1CC=C(C)C	standard polar	2025-10-24	2389.38
Gas Chromatography	trans-Isohumulone_TMS_26	CC(C)=CC=C(O[Si](C)(C)C)[C@]1(O[Si](C)(C)C)C(CC=C(C)C)=C(O[Si](C)(C)C)C(C(=O)CC(C)C)=C1O[Si](C)(C)C	standard polar	2025-10-24	3298.17
Gas Chromatography	trans-Isohumulone_TMS_27	CC(C)=CCC(=O)[C@]1(O[Si](C)(C)C)C(CC=C(C)C)=C(O[Si](C)(C)C)C(C(=CC(C)C)O[Si](C)(C)C)=C1O[Si](C)(C)C	standard polar	2025-10-24	1671.87
Gas Chromatography	trans-Isohumulone_TMS_28	CC(C)=CC=C(O[Si](C)(C)C)[C@@]1(O[Si](C)(C)C)C(O[Si](C)(C)C)=C(C(=CC(C)C)O[Si](C)(C)C)C(=O)[C@H]1CC=C(C)C	standard polar	2025-10-24	2631.47
Gas Chromatography	trans-Isohumulone_TMS_29	CC(C)=CC=C(O[Si](C)(C)C)[C@]1(O)C(CC=C(C)C)=C(O[Si](C)(C)C)C(C(=CC(C)C)O[Si](C)(C)C)=C1O[Si](C)(C)C	standard polar	2025-10-24	1618.2
Gas Chromatography	trans-Isohumulone_TMS_30	CC(C)=CC=C(O[Si](C)(C)C)[C@@]1(O[Si](C)(C)C)C(O)=C(C(=CC(C)C)O[Si](C)(C)C)C(O[Si](C)(C)C)=C1CC=C(C)C	standard polar	2025-10-24	1526.41
Gas Chromatography	trans-Isohumulone_TMS_31	CC(C)=CC=C(O[Si](C)(C)C)[C@]1(O[Si](C)(C)C)C(CC=C(C)C)=C(O[Si](C)(C)C)C(C(=CC(C)C)O[Si](C)(C)C)=C1O[Si](C)(C)C	standard polar	2025-10-24	2923.27

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Microbial Pathways

Pathways

Not Available

Metabolic Reactions

Reactions

This table shows at most 20 reactions. For the full list of associated reactions:

See All Associated Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Eukaryota/Fungi	Ascomycota	1	Human feces; Human saliva	Unknown

Exposure Sources

Other Exposures

Source Type	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11175902

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

CMMC Knowledgebase

Not Available

General References

Ramirez-Gaona M, Marcu A, Pon A, Guo AC, Sajed T, Wishart NA, Karu N, Djoumbou Feunang Y, Arndt D, Wishart DS: YMDB 2.0: a significantly expanded version of the yeast metabolome database. Nucleic Acids Res. 2017 Jan 4;45(D1):D440-D445. doi: 10.1093/nar/gkw1058. Epub 2016 Nov 28. [PubMed:27899612 ]

Showing metabocard for trans-Isohumulone (MMDBc0033722)

MOL for #<Metabolite:0x00007f9af20b7658>

3D MOL for #<Metabolite:0x00007f9af20b7658>

3D SDF for #<Metabolite:0x00007f9af20b7658>

3D-SDF for #<Metabolite:0x00007f9af20b7658>

PDB for #<Metabolite:0x00007f9af20b7658>

3D PDB for #<Metabolite:0x00007f9af20b7658>

SMILES for #<Metabolite:0x00007f9af20b7658>

INCHI for #<Metabolite:0x00007f9af20b7658>

Structure for #<Metabolite:0x00007f9af20b7658>

3D Structure for #<Metabolite:0x00007f9af20b7658>