MiMeDB: Showing metabocard for 3,5-Dimethylorsellinic acid (MMDBc0013686)

Record Information

Version

2.0

Status

Detected and Quantified

Creation Date

2021-05-15 04:57:12 UTC

Update Date

2025-10-07 16:06:10 UTC

Metabolite ID

MMDBc0013686

Metabolite Identification

Common Name

3,5-Dimethylorsellinic acid

Description

3,5-Dimethylorsellinic acid is a polyketide belonging to the class of aromatic metabolites. This compound is notable for its role as a precursor in the biosynthesis of various fungal meroterpenoids, which are hybrid molecules combining terpenoid and non-terpenoid components. Recent studies have highlighted its significance in the production of novel meroterpenoids, such as the four new 3,5-dimethylorsellinic acid-derived compounds co-isolated from the fungus Penicillium herquei (PMID:40091270 ) and the discovery of two undescribed meroterpenoids from Penicillium pancosmium (PMID:39395695 ). The compound's complex structure poses synthetic challenges, particularly for derivatives like the Berkeleyacetals (PMID:39903500 ). Additionally, the aromatic polyketide has been shown to influence conversion yields in enzymatic reactions, demonstrating a high preference for 3,5-dimethylorsellinic acid (PMID:36294566 ). Its involvement in the synthesis of depsides, such as Thielavin A, further underscores its biological relevance (PMID:38467568 ). Overall, 3,5-dimethylorsellinic acid serves as a critical building block in the diverse chemistry of fungal secondary metabolites.

Structure

MOL SDF PDB SMILES InChI


  Mrv1533004171515202D          

 14 14  0  0  0  0            999 V2000
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    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   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   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
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   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
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  5  9  2  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  2  0  0  0  0
  2 13  1  0  0  0  0
 13 14  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0013686

> <DATABASE_NAME>
MIME

> <SMILES>
CC1=C(C)C(C(O)=O)=C(O)C(C)=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C10H12O4/c1-4-5(2)8(11)6(3)9(12)7(4)10(13)14/h11-12H,1-3H3,(H,13,14)

> <INCHI_KEY>
NZGSNQJCTOMELT-UHFFFAOYSA-N

> <FORMULA>
C10H12O4

> <MOLECULAR_WEIGHT>
196.202

> <EXACT_MASS>
196.073558866

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
26

> <JCHEM_AVERAGE_POLARIZABILITY>
19.825184125767766

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2,4-dihydroxy-3,5,6-trimethylbenzoic acid

> <ALOGPS_LOGP>
1.52

> <JCHEM_LOGP>
3.213962248666667

> <ALOGPS_LOGS>
-1.80

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
10.599827061111402

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.9942700177083132

> <JCHEM_PKA_STRONGEST_BASIC>
-5.734627085840761

> <JCHEM_POLAR_SURFACE_AREA>
77.76

> <JCHEM_REFRACTIVITY>
52.39960000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.08e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2,4-dihydroxy-3,5,6-trimethylbenzoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 17-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-APR-15         0                                  
HETATM    1  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       4.001  -2.310   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0       5.335  -0.000   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      -1.334   2.310   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   13                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6    9                                                  
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6                                                            
CONECT    9    5   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11    2   14                                                  
CONECT   14   13                                                            
MASTER        0    0    0    0    0    0    0    0   14    0   28    0
END

Synonyms

Value	Source
DMOA	ChEBI
3,5-Dimethylorsellinate	Generator
2,4-Dihydroxy-3,5,6-trimethylbenzoate	Generator
3,5-Dimethylorsellinic acid	MeSH

Molecular Formula

C₁₀H₁₂O₄

Average Mass

196.202

Monoisotopic Mass

196.073558866

IUPAC Name

2,4-dihydroxy-3,5,6-trimethylbenzoic acid

Traditional Name

2,4-dihydroxy-3,5,6-trimethylbenzoic acid

CAS Registry Number

Not Available

SMILES

CC1=C(C)C(C(O)=O)=C(O)C(C)=C1O

InChI Identifier

InChI=1S/C10H12O4/c1-4-5(2)8(11)6(3)9(12)7(4)10(13)14/h11-12H,1-3H3,(H,13,14)

InChI Key

NZGSNQJCTOMELT-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as hydroxybenzoic acid derivatives. Hydroxybenzoic acid derivatives are compounds containing a hydroxybenzoic acid (or a derivative), which is a benzene ring bearing a carboxyl and a hydroxyl groups.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Benzoic acids and derivatives

Direct Parent

Hydroxybenzoic acid derivatives

Alternative Parents

Substituents

Dihydroxybenzoic acid
Hydroxybenzoic acid
Salicylic acid or derivatives
Salicylic acid
Benzoic acid
Benzoyl
M-cresol
O-cresol
P-cresol
Resorcinol
Phenol
Vinylogous acid
Carboxylic acid derivative
Carboxylic acid
Organooxygen compound
Organic oxygen compound
Hydrocarbon derivative
Organic oxide
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	3.08 g/L	ALOGPS
logP	1.52	ALOGPS
logP	3.21	ChemAxon
logS	-1.8	ALOGPS
pKa (Strongest Acidic)	2.99	ChemAxon
pKa (Strongest Basic)	-5.7	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	77.76 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	52.4 m³·mol⁻¹	ChemAxon
Polarizability	19.83 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_2_2) - 70eV, Positive	Not Available	2022-08-08	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	Not Available	2022-08-10	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	Not Available	2022-08-10	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	Not Available	2022-08-10	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	Not Available	2022-08-10	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	Not Available	2022-08-10	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	Not Available	2022-08-10	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 (eluted)	2025-10-23	50.4
Liquid Chromatography	HILIC	Accucore 150 Amide HILIC (eluted)	2025-10-23	28.2
Liquid Chromatography	Reversed-phase	Hypersil Gold 1.9 µm C18 (eluted)	2025-10-23	381.4
Liquid Chromatography	Reversed-phase	Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) (eluted)	2025-10-23	648.9
Liquid Chromatography	Reversed-phase	XBridge C18 3.5u 2.1x50 mm (eluted)	2025-10-23	564.9
Liquid Chromatography	Reversed-phase	Ascentis Express C18 (void)	2025-10-23	309.1
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-23	1384.0
Liquid Chromatography	HILIC	Merck SeQuant ZIC-HILIC (void)	2025-10-23	73.5
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC (eluted)	2025-10-23	404.2
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-23	303.2
Liquid Chromatography	HILIC	Merck SeQuant ZIC-HILIC (eluted)	2025-10-23	157.8
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-23	194.1
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-23	130.7
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC column (eluted)	2025-10-23	176.8
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC column (eluted)	2025-10-23	404.6
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-23	132.2
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-23	370.6
Liquid Chromatography	Reversed-phase	Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex (eluted)	2025-10-23	1352.0
Liquid Chromatography	Reversed-phase	Waters Atlantis T3 (2.1 x 150 mm, 5 um) (eluted)	2025-10-23	901.2

Retention Indices

Chromatography Type	Peak Label	SMILES	Stationary Phase	Deposition Date	Retention Index
Gas Chromatography	3,5-Dimethylorsellinic acid_TMS_1	CC1=C(C)C(C(=O)O[Si](C)(C)C)=C(O)C(C)=C1O	standard non polar	2025-10-23	2320.02
Gas Chromatography	3,5-Dimethylorsellinic acid_TMS_2	CC1=C(C)C(C(=O)O)=C(O[Si](C)(C)C)C(C)=C1O	standard non polar	2025-10-23	2653.61
Gas Chromatography	3,5-Dimethylorsellinic acid_TMS_3	CC1=C(C)C(C(=O)O)=C(O)C(C)=C1O[Si](C)(C)C	standard non polar	2025-10-23	2237.74
Gas Chromatography	3,5-Dimethylorsellinic acid_TMS_4	CC1=C(C)C(C(=O)O[Si](C)(C)C)=C(O[Si](C)(C)C)C(C)=C1O	standard non polar	2025-10-23	1418.41
Gas Chromatography	3,5-Dimethylorsellinic acid_TMS_5	CC1=C(C)C(C(=O)O[Si](C)(C)C)=C(O)C(C)=C1O[Si](C)(C)C	standard non polar	2025-10-23	1694.15
Gas Chromatography	3,5-Dimethylorsellinic acid_TMS_6	CC1=C(C)C(C(=O)O)=C(O[Si](C)(C)C)C(C)=C1O[Si](C)(C)C	standard non polar	2025-10-23	2169.7
Gas Chromatography	3,5-Dimethylorsellinic acid_TMS_7	CC1=C(C)C(C(=O)O[Si](C)(C)C)=C(O[Si](C)(C)C)C(C)=C1O[Si](C)(C)C	standard non polar	2025-10-23	2230.29
Gas Chromatography	3,5-Dimethylorsellinic acid_TMS_1	CC1=C(C)C(C(=O)O[Si](C)(C)C)=C(O)C(C)=C1O	standard polar	2025-10-23	1520.19
Gas Chromatography	3,5-Dimethylorsellinic acid_TMS_2	CC1=C(C)C(C(=O)O)=C(O[Si](C)(C)C)C(C)=C1O	standard polar	2025-10-23	1915.01
Gas Chromatography	3,5-Dimethylorsellinic acid_TMS_3	CC1=C(C)C(C(=O)O)=C(O)C(C)=C1O[Si](C)(C)C	standard polar	2025-10-23	2293.73
Gas Chromatography	3,5-Dimethylorsellinic acid_TMS_4	CC1=C(C)C(C(=O)O[Si](C)(C)C)=C(O[Si](C)(C)C)C(C)=C1O	standard polar	2025-10-23	1835.73
Gas Chromatography	3,5-Dimethylorsellinic acid_TMS_5	CC1=C(C)C(C(=O)O[Si](C)(C)C)=C(O)C(C)=C1O[Si](C)(C)C	standard polar	2025-10-23	1522.87
Gas Chromatography	3,5-Dimethylorsellinic acid_TMS_6	CC1=C(C)C(C(=O)O)=C(O[Si](C)(C)C)C(C)=C1O[Si](C)(C)C	standard polar	2025-10-23	2044.59
Gas Chromatography	3,5-Dimethylorsellinic acid_TMS_7	CC1=C(C)C(C(=O)O[Si](C)(C)C)=C(O[Si](C)(C)C)C(C)=C1O[Si](C)(C)C	standard polar	2025-10-23	2867.12

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

Not Available

KEGG Compound ID

Not Available

BioCyc ID

CPD-17316

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

19881764

PDB ID

Not Available

ChEBI ID

132131

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 3,5-Dimethylorsellinic acid (MMDBc0013686)

MOL for #<Metabolite:0x00007f2e08c906e8>

3D MOL for #<Metabolite:0x00007f2e08c906e8>

3D SDF for #<Metabolite:0x00007f2e08c906e8>

3D-SDF for #<Metabolite:0x00007f2e08c906e8>

PDB for #<Metabolite:0x00007f2e08c906e8>

3D PDB for #<Metabolite:0x00007f2e08c906e8>

SMILES for #<Metabolite:0x00007f2e08c906e8>

INCHI for #<Metabolite:0x00007f2e08c906e8>

Structure for #<Metabolite:0x00007f2e08c906e8>

3D Structure for #<Metabolite:0x00007f2e08c906e8>