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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2022-09-09 19:12:19 UTC

Update Date

2022-09-22 18:35:01 UTC

HMDB ID

HMDB0341124

Secondary Accession Numbers

None

Metabolite Identification

Common Name

9'-methylprotocetraric acid

Description

15-formyl-6,14-dihydroxy-7-(methoxymethyl)-4,12-dimethyl-10-oxo-2,9-dioxatricyclo[9.4.0.0³,⁸]pentadeca-1(11),3(8),4,6,12,14-hexaene-5-carboxylic acid belongs to the class of organic compounds known as depsides and depsidones. These are polycyclic compounds that is either a polyphenolic compound composed of two or more monocyclic aromatic units linked by an ester bond (depside), or a compound containing the depsidone structure (depsidone). 15-formyl-6,14-dihydroxy-7-(methoxymethyl)-4,12-dimethyl-10-oxo-2,9-dioxatricyclo[9.4.0.0³,⁸]pentadeca-1(11),3(8),4,6,12,14-hexaene-5-carboxylic acid is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv1533004201503282D          

 28 30  0  0  0  0            999 V2000
   -0.1329   -3.7753    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0506   -2.9710    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8390   -2.7278    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0226   -1.9235    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4178   -1.3623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3705   -1.6055    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6014   -0.5580    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0034    0.0031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1802    0.8075    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7917   -0.2400    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3897   -0.3148    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5733    0.4895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9945   -0.8760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7378   -0.5180    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4811   -0.8760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0859   -0.3148    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9023    0.4895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1139    0.7327    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8742   -0.5580    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4790    0.0031    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0578   -1.3623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4530   -1.9235    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6366   -2.7278    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6647   -1.6803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1503   -2.3253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5083   -3.0686    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3253   -2.3253    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8109   -1.6803    0.0000 C   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
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
  7 11  2  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 16 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  2  0  0  0  0
 15 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 25 27  1  0  0  0  0
 27 28  1  0  0  0  0
  4 28  1  0  0  0  0
 13 28  2  0  0  0  0
M  END


  Mrv1533004201503282D          

 28 30  0  0  0  0            999 V2000
   -0.1329   -3.7753    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0506   -2.9710    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8390   -2.7278    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0226   -1.9235    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4178   -1.3623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3705   -1.6055    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6014   -0.5580    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0034    0.0031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1802    0.8075    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7917   -0.2400    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3897   -0.3148    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5733    0.4895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9945   -0.8760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7378   -0.5180    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4811   -0.8760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0859   -0.3148    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9023    0.4895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1139    0.7327    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8742   -0.5580    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4790    0.0031    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0578   -1.3623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4530   -1.9235    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6366   -2.7278    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6647   -1.6803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1503   -2.3253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5083   -3.0686    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3253   -2.3253    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8109   -1.6803    0.0000 C   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
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
  7 11  2  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 16 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  2  0  0  0  0
 15 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 25 27  1  0  0  0  0
 27 28  1  0  0  0  0
  4 28  1  0  0  0  0
 13 28  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0341124

> <DATABASE_NAME>
hmdb

> <SMILES>
COCC1=C(O)C(C(O)=O)=C(C)C2=C1OC(=O)C1=C(C)C=C(O)C(C=O)=C1O2

> <INCHI_IDENTIFIER>
InChI=1S/C19H16O9/c1-7-4-11(21)9(5-20)16-12(7)19(25)28-17-10(6-26-3)14(22)13(18(23)24)8(2)15(17)27-16/h4-5,21-22H,6H2,1-3H3,(H,23,24)

> <INCHI_KEY>
IJJZZLYYFYYEHT-UHFFFAOYSA-N

> <FORMULA>
C19H16O9

> <MOLECULAR_WEIGHT>
388.328

> <EXACT_MASS>
388.079432095

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
44

> <JCHEM_AVERAGE_POLARIZABILITY>
37.72922436155094

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
15-formyl-6,14-dihydroxy-7-(methoxymethyl)-4,12-dimethyl-10-oxo-2,9-dioxatricyclo[9.4.0.0³,⁸]pentadeca-1(15),3(8),4,6,11,13-hexaene-5-carboxylic acid

> <ALOGPS_LOGP>
2.81

> <JCHEM_LOGP>
3.9272967199999993

> <ALOGPS_LOGS>
-3.75

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
7.26228990406487

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.551236124831585

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6420508497063993

> <JCHEM_POLAR_SURFACE_AREA>
139.59

> <JCHEM_REFRACTIVITY>
97.49519999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.85e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
15-formyl-6,14-dihydroxy-7-(methoxymethyl)-4,12-dimethyl-10-oxo-2,9-dioxatricyclo[9.4.0.0³,⁸]pentadeca-1(15),3(8),4,6,11,13-hexaene-5-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 20-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-APR-15         0                                  
HETATM    1  C   UNK     0      -0.248  -7.047   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       0.095  -5.546   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       1.566  -5.092   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.909  -3.590   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.780  -2.543   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      -0.692  -2.997   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       1.123  -1.042   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.006   0.006   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       0.336   1.507   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0      -1.478  -0.448   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       2.594  -0.588   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.937   0.914   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.723  -1.635   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       5.111  -0.967   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       6.498  -1.635   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       7.627  -0.588   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       7.284   0.914   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       5.813   1.368   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       9.099  -1.042   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      10.227   0.006   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       9.441  -2.543   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       8.312  -3.590   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       8.655  -5.092   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       6.841  -3.137   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       5.881  -4.341   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       6.549  -5.728   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0       4.341  -4.341   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       3.380  -3.137   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5   28                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8   11                                                  
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8                                                            
CONECT   11    7   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   28                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   24                                                  
CONECT   16   15   17   19                                                  
CONECT   17   16   18                                                       
CONECT   18   17                                                            
CONECT   19   16   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   15   25                                                  
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28                                                       
CONECT   28   27    4   13                                                  
MASTER        0    0    0    0    0    0    0    0   28    0   60    0
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
15-Formyl-6,14-dihydroxy-7-(methoxymethyl)-4,12-dimethyl-10-oxo-2,9-dioxatricyclo[9.4.0.0,]pentadeca-1(11),3(8),4,6,12,14-hexaene-5-carboxylate	Generator
15-Formyl-6,14-dihydroxy-7-(methoxymethyl)-4,12-dimethyl-10-oxo-2,9-dioxatricyclo[9.4.0.0³,⁸]pentadeca-1(11),3(8),4,6,12,14-hexaene-5-carboxylate	Generator

Chemical Formula

C₁₉H₁₆O₉

Average Molecular Weight

388.328

Monoisotopic Molecular Weight

388.079432095

IUPAC Name

15-formyl-6,14-dihydroxy-7-(methoxymethyl)-4,12-dimethyl-10-oxo-2,9-dioxatricyclo[9.4.0.0³,⁸]pentadeca-1(15),3(8),4,6,11,13-hexaene-5-carboxylic acid

Traditional Name

15-formyl-6,14-dihydroxy-7-(methoxymethyl)-4,12-dimethyl-10-oxo-2,9-dioxatricyclo[9.4.0.0³,⁸]pentadeca-1(15),3(8),4,6,11,13-hexaene-5-carboxylic acid

CAS Registry Number

Not Available

SMILES

COCC1=C(O)C(C(O)=O)=C(C)C2=C1OC(=O)C1=C(C)C=C(O)C(C=O)=C1O2

InChI Identifier

InChI=1S/C19H16O9/c1-7-4-11(21)9(5-20)16-12(7)19(25)28-17-10(6-26-3)14(22)13(18(23)24)8(2)15(17)27-16/h4-5,21-22H,6H2,1-3H3,(H,23,24)

InChI Key

IJJZZLYYFYYEHT-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as depsides and depsidones. These are polycyclic compounds that is either a polyphenolic compound composed of two or more monocyclic aromatic units linked by an ester bond (depside), or a compound containing the depsidone structure (depsidone).

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Depsides and depsidones

Sub Class

Not Available

Direct Parent

Depsides and depsidones

Alternative Parents

Substituents

Depsidone
Diaryl ether
Hydroxybenzoic acid
Salicylic acid or derivatives
1-hydroxy-2-unsubstituted benzenoid
Aryl-aldehyde
Dioxepine
1,4-dioxepine
Benzenoid
Dicarboxylic acid or derivatives
Vinylogous acid
Carboxylic acid ester
Lactone
Carboxylic acid derivative
Oxacycle
Carboxylic acid
Organoheterocyclic compound
Dialkyl ether
Ether
Organic oxide
Hydrocarbon derivative
Organic oxygen compound
Aldehyde
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	2.81	ALOGPS
logP	3.93	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Acidic)	2.55	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	139.59 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	97.5 m³·mol⁻¹	ChemAxon
Polarizability	37.73 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Kovats Retention Indices

Not Available

Spectra

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	34436864	details
Urine	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	34436864	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

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

138756195

PDB ID

Not Available

ChEBI ID

144178

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Neto FC, Raftery D: Expanding Urinary Metabolite Annotation through Integrated Mass Spectral Similarity Networking. Anal Chem. 2021 Sep 7;93(35):12001-12010. doi: 10.1021/acs.analchem.1c02041. Epub 2021 Aug 26. [PubMed:34436864 ]

Showing metabocard for 9'-methylprotocetraric acid (HMDB0341124)

MOL for HMDB0341124 (9'-methylprotocetraric acid)

3D MOL for HMDB0341124 (9'-methylprotocetraric acid)

3D SDF for HMDB0341124 (9'-methylprotocetraric acid)

3D-SDF for HMDB0341124 (9'-methylprotocetraric acid)

PDB for HMDB0341124 (9'-methylprotocetraric acid)

3D PDB for HMDB0341124 (9'-methylprotocetraric acid)

SMILES for HMDB0341124 (9'-methylprotocetraric acid)

INCHI for HMDB0341124 (9'-methylprotocetraric acid)

Structure for HMDB0341124 (9'-methylprotocetraric acid)

3D Structure for HMDB0341124 (9'-methylprotocetraric acid)

Predicted Kovats Retention Indices