NP-MRD: Showing NP-Card for 3,5-Dimethylorsellinic acid (NP0010750)

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Record Information

Version

2.0

Created at

2021-01-05 20:36:27 UTC

Updated at

2021-07-15 17:06:58 UTC

NP-MRD ID

NP0010750

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3,5-Dimethylorsellinic acid

Provided By

NPAtlas

Description

3,5-Dimethylorsellinic acid is also known as DMOA. 3,5-Dimethylorsellinic acid is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. 3,5-Dimethylorsellinic acid is found in Aspergillus nidulans. 3,5-Dimethylorsellinic acid was first documented in 2012 (PMID: 22549923). Based on a literature review a small amount of articles have been published on 3,5-dimethylorsellinic acid (PMID: 25216349) (PMID: 34343886).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242107403D          

 26 26  0  0  0  0            999 V2000
   -1.7005   -2.1745   -0.2734 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8295   -0.9722   -0.2936 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0664   -0.7564    0.8410 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1566   -1.6962    1.9955 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7679    0.3606    0.8548 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5682    0.5811    2.0429 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5034   -0.2196    3.0343 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4246    1.6499    2.1579 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8277    1.2200   -0.2279 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6201    2.3414   -0.2983 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0485    0.9923   -1.3750 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1094    1.9118   -2.5389 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7717   -0.1117   -1.3811 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5307   -0.3275   -2.5056 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4845   -2.0961    0.5046 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1647   -2.3110   -1.2633 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0949   -3.0934   -0.1119 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5399   -1.1800    2.9224 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7766   -2.2185    2.2252 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9557   -2.4424    1.7776 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2911    2.4354    2.7828 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2376    2.7161    0.3413 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1553    2.2324   -2.7575 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5489    2.7851   -2.3087 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3103    1.4089   -3.4172 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1761   -1.0357   -2.7279 H   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
 13 14  1  0  0  0  0
 13  2  1  0  0  0  0
  1 15  1  0  0  0  0
  1 16  1  0  0  0  0
  1 17  1  0  0  0  0
  4 18  1  0  0  0  0
  4 19  1  0  0  0  0
  4 20  1  0  0  0  0
  8 21  1  0  0  0  0
 10 22  1  0  0  0  0
 12 23  1  0  0  0  0
 12 24  1  0  0  0  0
 12 25  1  0  0  0  0
 14 26  1  0  0  0  0
M  END


  Mrv1652306242107403D          

 26 26  0  0  0  0            999 V2000
   -1.7005   -2.1745   -0.2734 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8295   -0.9722   -0.2936 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0664   -0.7564    0.8410 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1566   -1.6962    1.9955 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7679    0.3606    0.8548 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5682    0.5811    2.0429 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5034   -0.2196    3.0343 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4246    1.6499    2.1579 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8277    1.2200   -0.2279 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6201    2.3414   -0.2983 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0485    0.9923   -1.3750 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1094    1.9118   -2.5389 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7717   -0.1117   -1.3811 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5307   -0.3275   -2.5056 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4845   -2.0961    0.5046 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1647   -2.3110   -1.2633 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0949   -3.0934   -0.1119 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5399   -1.1800    2.9224 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7766   -2.2185    2.2252 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9557   -2.4424    1.7776 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2911    2.4354    2.7828 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2376    2.7161    0.3413 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1553    2.2324   -2.7575 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5489    2.7851   -2.3087 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3103    1.4089   -3.4172 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1761   -1.0357   -2.7279 H   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
 13 14  1  0  0  0  0
 13  2  1  0  0  0  0
  1 15  1  0  0  0  0
  1 16  1  0  0  0  0
  1 17  1  0  0  0  0
  4 18  1  0  0  0  0
  4 19  1  0  0  0  0
  4 20  1  0  0  0  0
  8 21  1  0  0  0  0
 10 22  1  0  0  0  0
 12 23  1  0  0  0  0
 12 24  1  0  0  0  0
 12 25  1  0  0  0  0
 14 26  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0010750

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC(=O)C1=C(O[H])C(=C(O[H])C(=C1C([H])([H])[H])C([H])([H])[H])C([H])([H])[H]

> <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>
19.858075286553003

> <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                                 24-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-JUN-21         0                                  
HETATM    1  C   UNK     0      -1.700  -2.175  -0.273  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.830  -0.972  -0.294  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.066  -0.756   0.841  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.157  -1.696   1.996  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.768   0.361   0.855  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.568   0.581   2.043  0.00  0.00           C+0
HETATM    7  O   UNK     0       1.503  -0.220   3.034  0.00  0.00           O+0
HETATM    8  O   UNK     0       2.425   1.650   2.158  0.00  0.00           O+0
HETATM    9  C   UNK     0       0.828   1.220  -0.228  0.00  0.00           C+0
HETATM   10  O   UNK     0       1.620   2.341  -0.298  0.00  0.00           O+0
HETATM   11  C   UNK     0       0.049   0.992  -1.375  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.109   1.912  -2.539  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.772  -0.112  -1.381  0.00  0.00           C+0
HETATM   14  O   UNK     0      -1.531  -0.328  -2.506  0.00  0.00           O+0
HETATM   15  H   UNK     0      -2.485  -2.096   0.505  0.00  0.00           H+0
HETATM   16  H   UNK     0      -2.165  -2.311  -1.263  0.00  0.00           H+0
HETATM   17  H   UNK     0      -1.095  -3.093  -0.112  0.00  0.00           H+0
HETATM   18  H   UNK     0      -0.540  -1.180   2.922  0.00  0.00           H+0
HETATM   19  H   UNK     0       0.777  -2.219   2.225  0.00  0.00           H+0
HETATM   20  H   UNK     0      -0.956  -2.442   1.778  0.00  0.00           H+0
HETATM   21  H   UNK     0       2.291   2.435   2.783  0.00  0.00           H+0
HETATM   22  H   UNK     0       2.238   2.716   0.341  0.00  0.00           H+0
HETATM   23  H   UNK     0       1.155   2.232  -2.757  0.00  0.00           H+0
HETATM   24  H   UNK     0      -0.549   2.785  -2.309  0.00  0.00           H+0
HETATM   25  H   UNK     0      -0.310   1.409  -3.417  0.00  0.00           H+0
HETATM   26  H   UNK     0      -2.176  -1.036  -2.728  0.00  0.00           H+0
CONECT    1    2   15   16   17                                             
CONECT    2    1    3   13                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3   18   19   20                                             
CONECT    5    3    6    9                                                  
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6   21                                                       
CONECT    9    5   10   11                                                  
CONECT   10    9   22                                                       
CONECT   11    9   12   13                                                  
CONECT   12   11   23   24   25                                             
CONECT   13   11   14    2                                                  
CONECT   14   13   26                                                       
CONECT   15    1                                                            
CONECT   16    1                                                            
CONECT   17    1                                                            
CONECT   18    4                                                            
CONECT   19    4                                                            
CONECT   20    4                                                            
CONECT   21    8                                                            
CONECT   22   10                                                            
CONECT   23   12                                                            
CONECT   24   12                                                            
CONECT   25   12                                                            
CONECT   26   14                                                            
MASTER        0    0    0    0    0    0    0    0   26    0   52    0
END

View in JSmol View NMR Assignments

Synonyms

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

Chemical Formula

C₁₀H₁₂O₄

Average Mass

196.2020 Da

Monoisotopic Mass

196.07356 Da

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(O)C(C)=C(O)C(C(O)=O)=C1C

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

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Aspergillus nidulans	NPAtlas	22510154

Chemical Taxonomy

Description

This compound belongs to the class of organic compounds known as hydroxybenzoic acid derivatives. These 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

Physical Properties

State

Not Available

Experimental 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

Predicted Properties

Property	Value	Source
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	19.86 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

External Links

NPAtlas ID

NPA013386

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

14455844

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

Good Scents ID

Not Available

References

General References

Itoh T, Tokunaga K, Radhakrishnan EK, Fujii I, Abe I, Ebizuka Y, Kushiro T: Identification of a key prenyltransferase involved in biosynthesis of the most abundant fungal meroterpenoids derived from 3,5-dimethylorsellinic acid. Chembiochem. 2012 May 29;13(8):1132-5. doi: 10.1002/cbic.201200124. Epub 2012 Apr 30. [PubMed:22549923 ]
Matsuda Y, Wakimoto T, Mori T, Awakawa T, Abe I: Complete biosynthetic pathway of anditomin: nature's sophisticated synthetic route to a complex fungal meroterpenoid. J Am Chem Soc. 2014 Oct 29;136(43):15326-36. doi: 10.1021/ja508127q. Epub 2014 Sep 23. [PubMed:25216349 ]
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Showing NP-Card for 3,5-Dimethylorsellinic acid (NP0010750)

MOL for NP0010750 (3,5-Dimethylorsellinic acid)

3D MOL for NP0010750 (3,5-Dimethylorsellinic acid)

3D SDF for NP0010750 (3,5-Dimethylorsellinic acid)

3D-SDF for NP0010750 (3,5-Dimethylorsellinic acid)

PDB for NP0010750 (3,5-Dimethylorsellinic acid)

3D PDB for NP0010750 (3,5-Dimethylorsellinic acid)

SMILES for NP0010750 (3,5-Dimethylorsellinic acid)

INCHI for NP0010750 (3,5-Dimethylorsellinic acid)

Structure for NP0010750 (3,5-Dimethylorsellinic acid)

3D Structure for NP0010750 (3,5-Dimethylorsellinic acid)