NP-MRD: Showing NP-Card for Olivetolic Acid (NP0084299)

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Record Information

Version

2.0

Created at

2022-04-29 05:04:30 UTC

Updated at

2022-04-29 05:04:30 UTC

NP-MRD ID

NP0084299

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Olivetolic Acid

Description

Olivetolic acid, also known as olivetolate, 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. Olivetolic Acid is found in Cannabis inflorescences. Olivetolic Acid was first documented in 2009 (PMID: 19454282). Olivetolic acid is an extremely weak basic (essentially neutral) compound (based on its pKa) (PMID: 22802619).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 32 32  0  0  0  0  0  0  0  0999 V2000
    3.2093    1.5964   -0.4572 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1759    0.5691    0.6424 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7452   -0.7571    0.1217 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3458   -0.7782   -0.4032 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3773   -0.5373    0.7500 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0304   -0.5543    0.2861 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6682   -1.8162    0.3235 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9430   -1.9883   -0.1530 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5973   -3.2253   -0.1285 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5802   -0.8934   -0.6665 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9931    0.3827   -0.7255 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7600    1.3517   -1.2620 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6975    0.5252   -0.2327 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0851    1.8181   -0.2385 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7226    2.8323   -0.6963 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1810    2.1387    0.2157 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1697    1.5135   -1.0158 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4030    1.4499   -1.1614 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1380    2.5968    0.0066 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5562    0.8909    1.5034 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2455    0.4830    0.9879 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8737   -1.4796    0.9743 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4860   -1.0347   -0.6979 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1295   -0.0294   -1.1633 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1001   -1.8123   -0.7739 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5334   -1.4615    1.3983 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6630    0.2826    1.3827 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1619   -2.6817    0.7295 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1648   -3.5254    0.6517 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5964   -1.0062   -1.0504 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7126    2.2879   -1.4619 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3806    2.8624    0.8873 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  8 10  2  0
 10 11  1  0
 11 12  1  0
 11 13  2  0
 13 14  1  0
 14 16  1  0
 14 15  2  0
 13  6  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  2 20  1  0
  2 21  1  0
  3 22  1  0
  3 23  1  0
  4 24  1  0
  4 25  1  0
  5 26  1  0
  5 27  1  0
  7 28  1  0
  9 29  1  0
 10 30  1  0
 12 31  1  0
 16 32  1  0
M  END

  Mrv1533004241513412D          

 16 16  0  0  0  0            999 V2000
    0.0000   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.9500    0.0000 O   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  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  2  0  0  0  0
  6 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0084299

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCCCC1=CC(O)=CC(O)=C1C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C12H16O4/c1-2-3-4-5-8-6-9(13)7-10(14)11(8)12(15)16/h6-7,13-14H,2-5H2,1H3,(H,15,16)

> <INCHI_KEY>
SXFKFRRXJUJGSS-UHFFFAOYSA-N

> <FORMULA>
C12H16O4

> <MOLECULAR_WEIGHT>
224.256

> <EXACT_MASS>
224.104858995

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
32

> <JCHEM_AVERAGE_POLARIZABILITY>
23.874710063144455

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
2.99

> <JCHEM_LOGP>
3.96539413

> <ALOGPS_LOGS>
-2.48

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
9.892573605379301

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.9499951932670054

> <JCHEM_PKA_STRONGEST_BASIC>
-5.766368179128844

> <JCHEM_POLAR_SURFACE_AREA>
77.76

> <JCHEM_REFRACTIVITY>
60.72120000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.46e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2,4-dihydroxy-6-pentylbenzoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-APR-15         0                                  
HETATM    1  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.668  -5.390   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.002  -4.620   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.336  -5.390   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      10.669  -4.620   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       9.336  -6.930   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.002  -7.700   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       8.002  -9.240   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       6.668  -6.930   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.335  -7.700   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       4.001  -6.930   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       5.335  -9.240   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   13                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11    6   14                                                  
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14                                                            
MASTER        0    0    0    0    0    0    0    0   16    0   32    0
END

View in JSmol

Synonyms

Value	Source
6-Pentyl-beta-resorcylic acid	ChEBI
Allazetolcarboxylic acid	ChEBI
Olivetolcarboxylic acid	ChEBI
6-Pentyl-b-resorcylate	Generator
6-Pentyl-b-resorcylic acid	Generator
6-Pentyl-beta-resorcylate	Generator
6-Pentyl-β-resorcylate	Generator
6-Pentyl-β-resorcylic acid	Generator
Allazetolcarboxylate	Generator
Olivetolcarboxylate	Generator
Olivetolate	Generator

Chemical Formula

C₁₂H₁₆O₄

Average Mass

224.2560 Da

Monoisotopic Mass

224.10486 Da

IUPAC Name

2,4-dihydroxy-6-pentylbenzoic acid

Traditional Name

2,4-dihydroxy-6-pentylbenzoic acid

CAS Registry Number

Not Available

SMILES

CCCCCC1=CC(O)=CC(O)=C1C(O)=O

InChI Identifier

InChI=1S/C12H16O4/c1-2-3-4-5-8-6-9(13)7-10(14)11(8)12(15)16/h6-7,13-14H,2-5H2,1H3,(H,15,16)

InChI Key

SXFKFRRXJUJGSS-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
Cannabis inflorescences	Plant	KNApSAcK

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
Salicylic acid or derivatives
Benzoic acid
Benzoyl
Resorcinol
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
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

monocarboxylic acid (CHEBI:66955 )
resorcinols (CHEBI:66955 )
polyketide (CHEBI:66955 )
benzoic acids (CHEBI:66955 )

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	2.99	ALOGPS
logP	3.97	ChemAxon
logS	-2.5	ALOGPS
pKa (Strongest Acidic)	2.95	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	5	ChemAxon
Refractivity	60.72 m³·mol⁻¹	ChemAxon
Polarizability	23.87 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

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

C20417

BioCyc ID

CPD-7165

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

66955

Good Scents ID

Not Available

References

General References

Taura F, Tanaka S, Taguchi C, Fukamizu T, Tanaka H, Shoyama Y, Morimoto S: Characterization of olivetol synthase, a polyketide synthase putatively involved in cannabinoid biosynthetic pathway. FEBS Lett. 2009 Jun 18;583(12):2061-6. doi: 10.1016/j.febslet.2009.05.024. Epub 2009 May 19. [PubMed:19454282 ]
Gagne SJ, Stout JM, Liu E, Boubakir Z, Clark SM, Page JE: Identification of olivetolic acid cyclase from Cannabis sativa reveals a unique catalytic route to plant polyketides. Proc Natl Acad Sci U S A. 2012 Jul 31;109(31):12811-6. doi: 10.1073/pnas.1200330109. Epub 2012 Jul 16. [PubMed:22802619 ]

Showing NP-Card for Olivetolic Acid (NP0084299)

MOL for NP0084299 (Olivetolic Acid)

3D MOL for NP0084299 (Olivetolic Acid)

3D SDF for NP0084299 (Olivetolic Acid)

3D-SDF for NP0084299 (Olivetolic Acid)

PDB for NP0084299 (Olivetolic Acid)

3D PDB for NP0084299 (Olivetolic Acid)

SMILES for NP0084299 (Olivetolic Acid)

INCHI for NP0084299 (Olivetolic Acid)

Structure for NP0084299 (Olivetolic Acid)

3D Structure for NP0084299 (Olivetolic Acid)