NP-MRD: Showing NP-Card for Orsellinic acid (NP0004781)

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Record Information

Version

2.0

Created at

2020-12-09 02:11:50 UTC

Updated at

2021-07-15 16:50:09 UTC

NP-MRD ID

NP0004781

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Orsellinic acid

Provided By

NPAtlas

Description

O-orsellinic acid, also known as orsellinate, 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. O-orsellinic 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. Orsellinic acid is found in Aspergillus fumigatus, Aspergillus oryzae, Auricularia delicata , Caetonium cochliodes, Cetrelia cetrarioides, Chaetomium, Chaetomium cochliodes, Nidularia pulvinata, Parmotrema stuppeum, Parmotrema tinctorum, Penicillium aurantiogriseum, Phomopsis velata, Stachybotrys cylindrospora, Umbilicaria torrefacta and Usnea longissima. Orsellinic acid was first documented in 1959 (PMID: 13648641). Based on a literature review a small amount of articles have been published on o-orsellinic acid (PMID: 20174687) (PMID: 13869400) (PMID: 19666480) (PMID: 20630753).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242121113D          

 20 20  0  0  0  0            999 V2000
   -1.2172    1.6841    0.9414 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1696    0.7915    0.3921 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1585    1.1759    0.5591 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1763    0.3905    0.0721 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4949    0.7596    0.2309 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8289   -0.7662   -0.5732 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4836   -1.1695   -0.7504 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2210   -2.3311   -1.4019 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5351   -0.3860   -0.2644 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9417   -0.6582   -0.3647 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8404    0.0983    0.1013 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4182   -1.7869   -0.9892 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7085    2.5799    1.4406 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8146    1.2320    1.7586 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8388    2.1205    0.1377 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4052    2.1007    1.0763 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0700    0.5039    1.0146 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5938   -1.3995   -0.9638 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6374   -2.7286   -1.5948 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3109   -2.2108   -0.8223 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
  4  5  1  0  0  0  0
  4  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
  9  2  1  0  0  0  0
  1 13  1  0  0  0  0
  1 14  1  0  0  0  0
  1 15  1  0  0  0  0
  3 16  1  0  0  0  0
  5 17  1  0  0  0  0
  6 18  1  0  0  0  0
  8 19  1  0  0  0  0
 12 20  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0004781

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C8H8O4/c1-4-2-5(9)3-6(10)7(4)8(11)12/h2-3,9-10H,1H3,(H,11,12)

> <INCHI_KEY>
AMKYESDOVDKZKV-UHFFFAOYSA-N

> <FORMULA>
C8H8O4

> <MOLECULAR_WEIGHT>
168.148

> <EXACT_MASS>
168.042258738

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
20

> <JCHEM_AVERAGE_POLARIZABILITY>
15.859536312445861

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2,4-dihydroxy-6-methylbenzoic acid

> <ALOGPS_LOGP>
1.44

> <JCHEM_LOGP>
2.18711947

> <ALOGPS_LOGS>
-1.43

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
9.91557083938119

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.9927404694969324

> <JCHEM_PKA_STRONGEST_BASIC>
-5.765196028213066

> <JCHEM_POLAR_SURFACE_AREA>
77.76

> <JCHEM_REFRACTIVITY>
42.3172

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.22e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
orsellinic 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      -1.217   1.684   0.941  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.170   0.792   0.392  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.159   1.176   0.559  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.176   0.391   0.072  0.00  0.00           C+0
HETATM    5  O   UNK     0       3.495   0.760   0.231  0.00  0.00           O+0
HETATM    6  C   UNK     0       1.829  -0.766  -0.573  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.484  -1.169  -0.750  0.00  0.00           C+0
HETATM    8  O   UNK     0       0.221  -2.331  -1.402  0.00  0.00           O+0
HETATM    9  C   UNK     0      -0.535  -0.386  -0.264  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.942  -0.658  -0.365  0.00  0.00           C+0
HETATM   11  O   UNK     0      -2.840   0.098   0.101  0.00  0.00           O+0
HETATM   12  O   UNK     0      -2.418  -1.787  -0.989  0.00  0.00           O+0
HETATM   13  H   UNK     0      -0.709   2.580   1.441  0.00  0.00           H+0
HETATM   14  H   UNK     0      -1.815   1.232   1.759  0.00  0.00           H+0
HETATM   15  H   UNK     0      -1.839   2.120   0.138  0.00  0.00           H+0
HETATM   16  H   UNK     0       1.405   2.101   1.076  0.00  0.00           H+0
HETATM   17  H   UNK     0       4.070   0.504   1.015  0.00  0.00           H+0
HETATM   18  H   UNK     0       2.594  -1.399  -0.964  0.00  0.00           H+0
HETATM   19  H   UNK     0      -0.637  -2.729  -1.595  0.00  0.00           H+0
HETATM   20  H   UNK     0      -3.311  -2.211  -0.822  0.00  0.00           H+0
CONECT    1    2   13   14   15                                             
CONECT    2    1    3    9                                                  
CONECT    3    2    4   16                                                  
CONECT    4    3    5    6                                                  
CONECT    5    4   17                                                       
CONECT    6    4    7   18                                                  
CONECT    7    6    8    9                                                  
CONECT    8    7   19                                                       
CONECT    9    7   10    2                                                  
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   20                                                       
CONECT   13    1                                                            
CONECT   14    1                                                            
CONECT   15    1                                                            
CONECT   16    3                                                            
CONECT   17    5                                                            
CONECT   18    6                                                            
CONECT   19    8                                                            
CONECT   20   12                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   40    0
END

View in JSmol View NMR Assignments

Synonyms

Value	Source
2,4-Dihydroxy-6-methylbenzoic acid	ChEBI
4,6-Dihydroxy-O-toluic acid	ChEBI
Orsellic acid	ChEBI
Orsellinic acid	ChEBI
Orsellinsaeure	ChEBI
2,4-Dihydroxy-6-methylbenzoate	Kegg
4,6-Dihydroxy-O-toluate	Generator
Orsellate	Generator
Orsellinate	Generator
O-Orsellinate	Generator
O-Orsellinic acid	KEGG

Chemical Formula

C₈H₈O₄

Average Mass

168.1480 Da

Monoisotopic Mass

168.04226 Da

IUPAC Name

2,4-dihydroxy-6-methylbenzoic acid

Traditional Name

orsellinic acid

CAS Registry Number

Not Available

SMILES

CC1=CC(O)=CC(O)=C1C(O)=O

InChI Identifier

InChI=1S/C8H8O4/c1-4-2-5(9)3-6(10)7(4)8(11)12/h2-3,9-10H,1H3,(H,11,12)

InChI Key

AMKYESDOVDKZKV-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 fumigatus	LOTUS Database	35616633
Aspergillus oryzae	LOTUS Database	35616633
Auricularia delicata	-	KNApSAcK
Caetonium cochliodes	-	KNApSAcK
Cetrelia cetrarioides	LOTUS Database	35616633
Chaetomium	NPAtlas	13648641
Chaetomium cochliodes	LOTUS Database	35616633
Nidularia pulvinata	LOTUS Database	35616633
Parmotrema stuppeum	LOTUS Database	35616633
Parmotrema tinctorum	LOTUS Database	35616633
Penicillium aurantiogriseum	LOTUS Database	35616633
Phomopsis velata	LOTUS Database	35616633
Stachybotrys cylindrospora	LOTUS Database	35616633
Umbilicaria torrefacta	LOTUS Database	35616633
Usnea longissima	LOTUS Database	35616633

Species Where Detected

Species Name	Source	Reference
Hypoxylon rubiginosum	KNApSAcK Database	22123792
Lobaria yunnanensis	KNApSAcK Database	22123792
Penicillium cyclopium	KNApSAcK Database	22123792
Stereum hirsutum	KNApSAcK Database	22123792
Umbilicaria hypococcinea	KNApSAcK Database	22123792

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
Resorcinol
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Toluene
Vinylogous acid
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Organooxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

resorcinols (CHEBI:32807 )
dihydroxybenzoic acid (CHEBI:32807 )
Monocyclic aromatic polyketides (C01839 )
Monocyclic aromatic polyketides (LMPK13010001 )

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	1.44	ALOGPS
logP	2.19	ChemAxon
logS	-1.4	ALOGPS
pKa (Strongest Acidic)	2.99	ChemAxon
pKa (Strongest Basic)	-5.8	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	42.32 m³·mol⁻¹	ChemAxon
Polarizability	15.86 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

NPA024876

HMDB ID

HMDB0150427

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Orsellinic_acid

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

32807

Good Scents ID

Not Available

References

General References

MOSBACH K: [Presence of orsellinic acid in Chaetomium cochliodes]. Z Naturforsch B. 1959 Jan;14B(1):69-70. [PubMed:13648641 ]
Sanchez JF, Chiang YM, Szewczyk E, Davidson AD, Ahuja M, Elizabeth Oakley C, Woo Bok J, Keller N, Oakley BR, Wang CC: Molecular genetic analysis of the orsellinic acid/F9775 gene cluster of Aspergillus nidulans. Mol Biosyst. 2010 Mar;6(3):587-93. doi: 10.1039/b904541d. Epub 2009 Dec 16. [PubMed:20174687 ]
BIRKINSHAW JH, GOWLLAND A: Studies in the biochemistry of micro-organisms. 110. Production and biosynthesis of orsellinic acid by Penicillium madriti G. Smith. Biochem J. 1962 Aug;84:342-7. doi: 10.1042/bj0840342. [PubMed:13869400 ]
Schroeckh V, Scherlach K, Nutzmann HW, Shelest E, Schmidt-Heck W, Schuemann J, Martin K, Hertweck C, Brakhage AA: Intimate bacterial-fungal interaction triggers biosynthesis of archetypal polyketides in Aspergillus nidulans. Proc Natl Acad Sci U S A. 2009 Aug 25;106(34):14558-63. doi: 10.1073/pnas.0901870106. Epub 2009 Aug 6. [PubMed:19666480 ]
Seshime Y, Juvvadi PR, Kitamoto K, Ebizuka Y, Nonaka T, Fujii I: Aspergillus oryzae type III polyketide synthase CsyA is involved in the biosynthesis of 3,5-dihydroxybenzoic acid. Bioorg Med Chem Lett. 2010 Aug 15;20(16):4785-8. doi: 10.1016/j.bmcl.2010.06.119. Epub 2010 Jun 25. [PubMed:20630753 ]

Showing NP-Card for Orsellinic acid (NP0004781)

MOL for NP0004781 (Orsellinic acid)

3D MOL for NP0004781 (Orsellinic acid)

3D SDF for NP0004781 (Orsellinic acid)

3D-SDF for NP0004781 (Orsellinic acid)

PDB for NP0004781 (Orsellinic acid)

3D PDB for NP0004781 (Orsellinic acid)

SMILES for NP0004781 (Orsellinic acid)

INCHI for NP0004781 (Orsellinic acid)

Structure for NP0004781 (Orsellinic acid)

3D Structure for NP0004781 (Orsellinic acid)