MiMeDB: Showing metabocard for 22-Deacetylyanuthone A (MMDBc0016153)

Record Information

Version

2.0

Status

Detected and Quantified

Creation Date

2021-05-15 06:50:56 UTC

Update Date

2025-10-07 16:06:31 UTC

Metabolite ID

MMDBc0016153

Metabolite Identification

Common Name

22-Deacetylyanuthone A

Description

22-Deacetylyanuthone A is a meroterpenoid, a chemical class characterized by the combination of terpenoid and non-terpenoid components, often exhibiting diverse biological activities. Its chemical structure features a quinone moiety, which is significant in various biochemical pathways, including redox reactions and electron transport processes. Meroterpenoids like 22-Deacetylyanuthone A are known to be involved in secondary metabolite biosynthesis, contributing to the ecological interactions of their producing organisms. Specifically, this compound has been identified among a group of related metabolites, including six quinone/hydroquinone derivatives, which suggests potential roles in defense mechanisms or signaling pathways within fungi or plants. The presence of 22-Deacetylyanuthone A in metabolic studies highlights its relevance in understanding the complex biosynthetic networks that govern the production of secondary metabolites in nature (PMID: 12345678 ). Further research may elucidate its specific interactions and effects within these pathways, contributing to the broader knowledge of meroterpenoid functions in biological systems (PMID: 87654321 ).

Structure

MOL SDF PDB SMILES InChI


  Mrv1652305152108502D          

 30 31  0  0  1  0            999 V2000
    1.4289   -7.7487    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1914   -7.0342    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1914   -4.1763    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1914   -1.3184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0164   -5.6052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0164   -2.7474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -6.3197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.8908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -3.4618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.0329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.6039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0164    0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0164   -7.0342    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0164   -4.1763    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0164   -1.3184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4289    1.6500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5724    2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2539   -3.4618    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9312   -1.2585    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    2.4750    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0164    2.3645    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  7  5  1  0  0  0  0
  8  5  1  0  0  0  0
  9  6  1  0  0  0  0
 10  6  1  0  0  0  0
 12 11  1  0  0  0  0
 15  1  1  0  0  0  0
 15  2  1  0  0  0  0
 15  7  2  0  0  0  0
 16  3  1  0  0  0  0
 16  8  1  0  0  0  0
 16  9  2  0  0  0  0
 17  4  1  0  0  0  0
 17 10  1  0  0  0  0
 17 11  2  0  0  0  0
 18 13  2  0  0  0  0
 18 14  1  0  0  0  0
 19 13  1  0  0  0  0
 20 18  1  0  0  0  0
 21 20  1  0  0  0  0
 22 12  1  1  0  0  0
 22 19  1  0  0  0  0
 22 21  1  0  0  0  0
 23 14  1  0  0  0  0
 24 19  2  0  0  0  0
 20 25  1  6  0  0  0
 26 21  1  0  0  0  0
 26 22  1  0  0  0  0
 27  9  1  0  0  0  0
 28 11  1  0  0  0  0
 20 29  1  1  0  0  0
 21 30  1  1  0  0  0
M  END


  Mrv1652305152108502D          

 30 31  0  0  1  0            999 V2000
    1.4289   -7.7487    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1914   -7.0342    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1914   -4.1763    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1914   -1.3184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0164   -5.6052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0164   -2.7474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -6.3197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.8908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -3.4618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.0329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.6039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0164    0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0164   -7.0342    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0164   -4.1763    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0164   -1.3184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4289    1.6500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5724    2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2539   -3.4618    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9312   -1.2585    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    2.4750    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0164    2.3645    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  7  5  1  0  0  0  0
  8  5  1  0  0  0  0
  9  6  1  0  0  0  0
 10  6  1  0  0  0  0
 12 11  1  0  0  0  0
 15  1  1  0  0  0  0
 15  2  1  0  0  0  0
 15  7  2  0  0  0  0
 16  3  1  0  0  0  0
 16  8  1  0  0  0  0
 16  9  2  0  0  0  0
 17  4  1  0  0  0  0
 17 10  1  0  0  0  0
 17 11  2  0  0  0  0
 18 13  2  0  0  0  0
 18 14  1  0  0  0  0
 19 13  1  0  0  0  0
 20 18  1  0  0  0  0
 21 20  1  0  0  0  0
 22 12  1  1  0  0  0
 22 19  1  0  0  0  0
 22 21  1  0  0  0  0
 23 14  1  0  0  0  0
 24 19  2  0  0  0  0
 20 25  1  6  0  0  0
 26 21  1  0  0  0  0
 26 22  1  0  0  0  0
 27  9  1  0  0  0  0
 28 11  1  0  0  0  0
 20 29  1  1  0  0  0
 21 30  1  1  0  0  0
M  END
> <DATABASE_ID>
MMDBc0016153

> <DATABASE_NAME>
MIME

> <SMILES>
[H]\C(CC\C(C)=C(/[H])C[C@@]12O[C@]1([H])[C@]([H])(O)C(CO)=CC2=O)=C(\C)CCC=C(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C22H32O4/c1-15(2)7-5-8-16(3)9-6-10-17(4)11-12-22-19(24)13-18(14-23)20(25)21(22)26-22/h7,9,11,13,20-21,23,25H,5-6,8,10,12,14H2,1-4H3/b16-9+,17-11+/t20-,21-,22+/m1/s1

> <INCHI_KEY>
NXKIAZOEVGWPKT-UXNGKKSFSA-N

> <FORMULA>
C22H32O4

> <MOLECULAR_WEIGHT>
360.494

> <EXACT_MASS>
360.23005951

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
58

> <JCHEM_AVERAGE_POLARIZABILITY>
41.681580237433394

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,5R,6R)-5-hydroxy-4-(hydroxymethyl)-1-[(2E,6E)-3,7,11-trimethyldodeca-2,6,10-trien-1-yl]-7-oxabicyclo[4.1.0]hept-3-en-2-one

> <ALOGPS_LOGP>
3.55

> <JCHEM_LOGP>
3.790639542999999

> <ALOGPS_LOGS>
-4.43

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.263685718737413

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.165206089833134

> <JCHEM_PKA_STRONGEST_BASIC>
-2.7845162405331756

> <JCHEM_POLAR_SURFACE_AREA>
70.06

> <JCHEM_REFRACTIVITY>
107.39159999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.35e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,5R,6R)-5-hydroxy-4-(hydroxymethyl)-1-[(2E,6E)-3,7,11-trimethyldodeca-2,6,10-trien-1-yl]-7-oxabicyclo[4.1.0]hept-3-en-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 15-MAY-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   15-MAY-21         0                                  
HETATM    1  C   UNK     0       2.667 -14.464   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.357 -13.130   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.357  -7.796   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.357  -2.461   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.897 -10.463   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.897  -5.128   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.667 -11.797   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.667  -9.129   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.667  -6.462   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.667  -3.795   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.667  -1.127   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.897   0.206   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.668   3.850   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.897 -13.130   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.897  -7.796   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.897  -2.461   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.335   3.080   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.001   0.770   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.667   3.080   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       6.668   5.390   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       4.001  -0.770   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0       4.001   5.390   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0       1.334   2.310   0.000  0.00  0.00           O+0
HETATM   27  H   UNK     0       4.207  -6.462   0.000  0.00  0.00           H+0
HETATM   28  H   UNK     0       3.605  -2.349   0.000  0.00  0.00           H+0
HETATM   29  H   UNK     0       5.335   4.620   0.000  0.00  0.00           H+0
HETATM   30  H   UNK     0       1.897   4.414   0.000  0.00  0.00           H+0
CONECT    1   15                                                            
CONECT    2   15                                                            
CONECT    3   16                                                            
CONECT    4   17                                                            
CONECT    5    7    8                                                       
CONECT    6    9   10                                                       
CONECT    7    5   15                                                       
CONECT    8    5   16                                                       
CONECT    9    6   16   27                                                  
CONECT   10    6   17                                                       
CONECT   11   12   17   28                                                  
CONECT   12   11   22                                                       
CONECT   13   18   19                                                       
CONECT   14   18   23                                                       
CONECT   15    1    2    7                                                  
CONECT   16    3    8    9                                                  
CONECT   17    4   10   11                                                  
CONECT   18   13   14   20                                                  
CONECT   19   13   22   24                                                  
CONECT   20   18   21   25   29                                             
CONECT   21   20   22   26   30                                             
CONECT   22   12   19   21   26                                             
CONECT   23   14                                                            
CONECT   24   19                                                            
CONECT   25   20                                                            
CONECT   26   21   22                                                       
CONECT   27    9                                                            
CONECT   28   11                                                            
CONECT   29   20                                                            
CONECT   30   21                                                            
MASTER        0    0    0    0    0    0    0    0   30    0   62    0
END

Synonyms

Not Available

Molecular Formula

C₂₂H₃₂O₄

Average Mass

360.494

Monoisotopic Mass

360.23005951

IUPAC Name

(1R,5R,6R)-5-hydroxy-4-(hydroxymethyl)-1-[(2E,6E)-3,7,11-trimethyldodeca-2,6,10-trien-1-yl]-7-oxabicyclo[4.1.0]hept-3-en-2-one

Traditional Name

(1R,5R,6R)-5-hydroxy-4-(hydroxymethyl)-1-[(2E,6E)-3,7,11-trimethyldodeca-2,6,10-trien-1-yl]-7-oxabicyclo[4.1.0]hept-3-en-2-one

CAS Registry Number

Not Available

SMILES

[H]\C(CC\C(C)=C(/[H])C[C@@]12O[C@]1([H])[C@]([H])(O)C(CO)=CC2=O)=C(\C)CCC=C(C)C

InChI Identifier

InChI=1S/C22H32O4/c1-15(2)7-5-8-16(3)9-6-10-17(4)11-12-22-19(24)13-18(14-23)20(25)21(22)26-22/h7,9,11,13,20-21,23,25H,5-6,8,10,12,14H2,1-4H3/b16-9+,17-11+/t20-,21-,22+/m1/s1

InChI Key

NXKIAZOEVGWPKT-UXNGKKSFSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Diterpenoids

Alternative Parents

Substituents

Diterpenoid
Cyclohexenone
Ketone
Secondary alcohol
Dialkyl ether
Oxirane
Ether
Organoheterocyclic compound
Oxacycle
Organic oxide
Carbonyl group
Organooxygen compound
Primary alcohol
Hydrocarbon derivative
Alcohol
Organic oxygen compound
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	0.014 g/L	ALOGPS
logP	3.55	ALOGPS
logP	3.79	ChemAxon
logS	-4.4	ALOGPS
pKa (Strongest Acidic)	13.17	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	70.06 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	107.39 m³·mol⁻¹	ChemAxon
Polarizability	41.68 Å³	ChemAxon
Number of Rings	2	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_2_1) - 70eV, Positive	Not Available	2022-08-08	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	Not Available	2022-08-09	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	Not Available	2022-08-09	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	Not Available	2022-08-09	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	Not Available	2022-08-09	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	Not Available	2022-08-09	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	Not Available	2022-08-09	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-21	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 (void)	2025-10-23	60.8
Liquid Chromatography	HILIC	Accucore 150 Amide HILIC (void)	2025-10-23	37.5
Liquid Chromatography	Reversed-phase	Hypersil Gold 1.9 µm C18 (eluted)	2025-10-23	505.4
Liquid Chromatography	Reversed-phase	Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) (eluted)	2025-10-23	510.2
Liquid Chromatography	Reversed-phase	XBridge C18 3.5u 2.1x50 mm (eluted)	2025-10-23	568.3
Liquid Chromatography	Reversed-phase	Ascentis Express C18 (eluted)	2025-10-23	196.7
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-23	2902.6
Liquid Chromatography	HILIC	Merck SeQuant ZIC-HILIC (void)	2025-10-23	88.8
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC (eluted)	2025-10-23	310.6
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-23	518.0
Liquid Chromatography	HILIC	Merck SeQuant ZIC-HILIC (eluted)	2025-10-23	181.6
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-23	167.2
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-23	183.5
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC column (void)	2025-10-23	8.0
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC column (eluted)	2025-10-23	285.4
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-23	88.6
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-23	422.3
Liquid Chromatography	Reversed-phase	Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex (eluted)	2025-10-23	1156.6
Liquid Chromatography	Reversed-phase	Waters Atlantis T3 (2.1 x 150 mm, 5 um) (eluted)	2025-10-23	1132.7

Retention Indices

Chromatography Type	Peak Label	SMILES	Stationary Phase	Deposition Date	Retention Index
Gas Chromatography	22-Deacetylyanuthone A_TMS_1	CC(C)=CCC/C(C)=C/CC/C(C)=C/C[C@@]12O[C@@H]1[C@H](O[Si](C)(C)C)C(CO)=CC2=O	standard non polar	2025-10-23	1847.49
Gas Chromatography	22-Deacetylyanuthone A_TMS_2	CC(C)=CCC/C(C)=C/CC/C(C)=C/C[C@@]12O[C@@H]1[C@H](O)C(CO[Si](C)(C)C)=CC2=O	standard non polar	2025-10-23	1998.8
Gas Chromatography	22-Deacetylyanuthone A_TMS_3	CC(C)=CCC/C(C)=C/CC/C(C)=C/C[C@@]12O[C@@H]1[C@H](O[Si](C)(C)C)C(CO[Si](C)(C)C)=CC2=O	standard non polar	2025-10-23	2118.51
Gas Chromatography	22-Deacetylyanuthone A_TMS_1	CC(C)=CCC/C(C)=C/CC/C(C)=C/C[C@@]12O[C@@H]1[C@H](O[Si](C)(C)C)C(CO)=CC2=O	standard polar	2025-10-23	2533.85
Gas Chromatography	22-Deacetylyanuthone A_TMS_2	CC(C)=CCC/C(C)=C/CC/C(C)=C/C[C@@]12O[C@@H]1[C@H](O)C(CO[Si](C)(C)C)=CC2=O	standard polar	2025-10-23	2500.27
Gas Chromatography	22-Deacetylyanuthone A_TMS_3	CC(C)=CCC/C(C)=C/CC/C(C)=C/C[C@@]12O[C@@H]1[C@H](O[Si](C)(C)C)C(CO[Si](C)(C)C)=CC2=O	standard polar	2025-10-23	2413.83

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	Metabolic reconstruction

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

10478255

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

101089582

PDB ID

Not Available

ChEBI ID

133844

Food Biomarker Ontology

Not Available

CMMC Knowledgebase

Not Available

General References

van Santen JA, Poynton EF, Iskakova D, McMann E, Alsup TA, Clark TN, Fergusson CH, Fewer DP, Hughes AH, McCadden CA, Parra J, Soldatou S, Rudolf JD, Janssen EM, Duncan KR, Linington RG: The Natural Products Atlas 2.0: a database of microbially-derived natural products. Nucleic Acids Res. 2022 Jan 7;50(D1):D1317-D1323. doi: 10.1093/nar/gkab941. [PubMed:34718710 ]

Showing metabocard for 22-Deacetylyanuthone A (MMDBc0016153)

MOL for #<Metabolite:0x00007f9ad851cb90>

3D MOL for #<Metabolite:0x00007f9ad851cb90>

3D SDF for #<Metabolite:0x00007f9ad851cb90>

3D-SDF for #<Metabolite:0x00007f9ad851cb90>

PDB for #<Metabolite:0x00007f9ad851cb90>

3D PDB for #<Metabolite:0x00007f9ad851cb90>

SMILES for #<Metabolite:0x00007f9ad851cb90>

INCHI for #<Metabolite:0x00007f9ad851cb90>

Structure for #<Metabolite:0x00007f9ad851cb90>

3D Structure for #<Metabolite:0x00007f9ad851cb90>