NP-MRD: Showing NP-Card for Olivetol (NP0138956)

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Record Information

Version

2.0

Created at

2022-06-29 19:33:16 UTC

Updated at

2022-06-29 19:33:16 UTC

NP-MRD ID

NP0138956

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Olivetol

Description

Olivetol belongs to the class of organic compounds known as resorcinols. Resorcinols are compounds containing a resorcinol moiety, which is a benzene ring bearing two hydroxyl groups at positions 1 and 3. Olivetol is a naturally occurring organic compound. Olivetol is an extremely weak basic (essentially neutral) compound (based on its pKa). The cannabis plant internally produces the related substance olivetolic acid (OLA), which may be involved in the biosynthesis of tetrahydrocannabinol (THC). The production, possession, and/or distribution of olivetol is not outlawed by any country; however, in the United States, it is a DEA watched precursor. Olivetol is biosynthesized by a polyketide synthase-type reaction from hexanoyl-CoA and three molecules of malonyl-CoA by an aldol condensation of a tetraketide intermediate. In PiHKAL, Alexander Shulgin reports a cruder method of producing the same product by bringing to reaction olivetol and the essential oil of orange in the presence of phosphoryl chloride. The exact mechanism of olivetol biosynthesis is as yet unsure, but it is possible that an OLA-forming metabolic complex forms along with OLS. Olivetol is found in Ardisia virens, Cannabis sativa and Primula obconica. Olivetol was first documented in 1984 (PMID: 6512535). The data from Taura's study of OLS's enzyme kinetics show that OLS catalyzes a decarboxylative-aldol condensation to produce olivetol (PMID: 19454282) (PMID: 22802619).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 29 29  0  0  0  0  0  0  0  0999 V2000
    3.9304    0.5273   -0.2560 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5836   -0.9085   -0.5171 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3315   -1.2707    0.2555 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1576   -0.4053   -0.1613 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0259   -0.8213    0.6387 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2584   -0.0827    0.3622 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6436    1.0666    1.0112 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8250    1.6909    0.6791 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2039    2.8453    1.3368 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6311    1.1783   -0.2991 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2794    0.0149   -0.9830 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1070   -0.4965   -1.9754 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0948   -0.5724   -0.6190 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7711    0.7302    0.8265 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4217    1.2390   -0.9158 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0261    0.6451   -0.4225 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4725   -1.1242   -1.5935 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4026   -1.5310   -0.0999 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0313   -2.3208    0.0643 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5241   -1.0661    1.3279 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9273   -0.6232   -1.2396 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4360    0.6420   -0.0880 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2024   -1.9030    0.4568 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2466   -0.7379    1.7196 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0046    1.4513    1.7694 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7601    2.8159    2.1720 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5566    1.6772   -0.5514 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8471   -1.1763   -1.7409 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8227   -1.4840   -1.1575 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  6  1  0
  1 14  1  0
  1 15  1  0
  1 16  1  0
  2 17  1  0
  2 18  1  0
  3 19  1  0
  3 20  1  0
  4 21  1  0
  4 22  1  0
  5 23  1  0
  5 24  1  0
  7 25  1  0
  9 26  1  0
 10 27  1  0
 12 28  1  0
 13 29  1  0
M  END

HEADER    PROTEIN                                 27-APR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-APR-20         0                                  
HETATM    1  C   UNK     0       1.540  -8.002   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.770  -6.669   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.540  -5.335   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.770  -4.001   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.540  -2.667   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.540   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.770  -1.334   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.770   1.334   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.770  -1.334   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.770   1.334   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.540   0.000   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       1.540   2.667   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0      -3.080   0.000   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    9                                                       
CONECT    6    9   10                                                       
CONECT    7    9   11                                                       
CONECT    8   10   11                                                       
CONECT    9    5    6    7                                                  
CONECT   10    6    8   12                                                  
CONECT   11    7    8   13                                                  
CONECT   12   10                                                            
CONECT   13   11                                                            
MASTER        0    0    0    0    0    0    0    0   13    0   26    0
END

View in JSmol

Synonyms

Value	Source
3,5-Dihydroxyamylbenzene	ChEBI
5-(1-Pentyl)resorcinol	ChEBI
5-N-Amylresorcinol	ChEBI
5-N-Pentylresorcinol	ChEBI
5-Pentyl-1,3-benzenediol	ChEBI
5-Pentylresorcinol	ChEBI
5-Pentyl-1,3-dihydroxybenzene	MeSH

Chemical Formula

C₁₁H₁₆O₂

Average Mass

180.2470 Da

Monoisotopic Mass

180.11503 Da

IUPAC Name

5-pentylbenzene-1,3-diol

Traditional Name

olivetol

CAS Registry Number

Not Available

SMILES

CCCCCC1=CC(O)=CC(O)=C1

InChI Identifier

InChI=1S/C11H16O2/c1-2-3-4-5-9-6-10(12)8-11(13)7-9/h6-8,12-13H,2-5H2,1H3

InChI Key

IRMPFYJSHJGOPE-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, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, 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
Ardisia virens	LOTUS Database	35616633
Cannabis sativa	LOTUS Database	35616633
Primula obconica	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as resorcinols. Resorcinols are compounds containing a resorcinol moiety, which is a benzene ring bearing two hydroxyl groups at positions 1 and 3.

Kingdom

Super Class

Class

Sub Class

Direct Parent

Alternative Parents

Substituents

Resorcinol
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Monocyclic benzene moiety
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

resorcinols (CHEBI:66960 )
a polyketide (CPD-11505 )

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	3.16	ALOGPS
logP	3.66	ChemAxon
logS	-2.3	ALOGPS
pKa (Strongest Acidic)	9.36	ChemAxon
pKa (Strongest Basic)	-5.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	40.46 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	53.46 m³·mol⁻¹	ChemAxon
Polarizability	20.99 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

Not Available

BioCyc ID

CPD-11505

BiGG ID

Not Available

Wikipedia Link

Olivetol

METLIN ID

Not Available

PubChem Compound

10377

PDB ID

Not Available

ChEBI ID

66960

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 ]
McClanahan RH, Robertson LW: Biotransformation of olivetol by Syncephalastrum racemosum. J Nat Prod. 1984 Sep-Oct;47(5):828-34. doi: 10.1021/np50035a013. [PubMed:6512535 ]

Showing NP-Card for Olivetol (NP0138956)

MOL for NP0138956 (Olivetol)

3D MOL for NP0138956 (Olivetol)

3D SDF for NP0138956 (Olivetol)

3D-SDF for NP0138956 (Olivetol)

PDB for NP0138956 (Olivetol)

3D PDB for NP0138956 (Olivetol)

SMILES for NP0138956 (Olivetol)

INCHI for NP0138956 (Olivetol)

Structure for NP0138956 (Olivetol)

3D Structure for NP0138956 (Olivetol)