NP-MRD: Showing NP-Card for CBDQ (NP0332906)

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Record Information

Version

1.0

Created at

2024-05-02 00:28:48 UTC

Updated at

2024-05-03 00:10:58 UTC

NP-MRD ID

NP0332906

Secondary Accession Numbers

None

Natural Product Identification

Common Name

CBDQ

Description

Cannabidiol hydroxyquinone, also known as CBDHQ, belongs to the class of organic compounds known as prenylquinones. These are quinones with a structure characterized by the quinone ring substituted by an prenyl side-chain. It was first documented in 2006 (PMID: 16571653). Based on a literature review a small amount of articles have been published on Cannabidiol hydroxyquinone (PMID: 36414659) (PMID: 20184945).

Structure

MOL SDF PDB SMILES InChI


  Mrv2104 01142303052D          

 25 26  0  0  1  0            999 V2000
   -2.1434   -6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -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
   -3.5724   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -5.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -5.3625    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.5724   -4.5375    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -6.1875    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8579   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0374   -6.6862    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7158   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868   -4.9500    0.0000 C   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  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  4 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
  3 13  2  0  0  0  0
  2 14  2  0  0  0  0
 11 14  1  0  0  0  0
 15 14  1  0  0  0  0
 15 16  1  6  0  0  0
 15 17  1  0  0  0  0
 17 18  1  6  0  0  0
 18 19  1  0  0  0  0
 18 20  2  0  0  0  0
 17 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 23 25  2  0  0  0  0
 15 25  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0332906

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@]1(C=C(C)CC[C@H]1C(C)=C)C1=C(O)C(=O)C(CCCCC)=CC1=O

> <INCHI_IDENTIFIER>
InChI=1S/C21H28O3/c1-5-6-7-8-15-12-18(22)19(21(24)20(15)23)17-11-14(4)9-10-16(17)13(2)3/h11-12,16-17,24H,2,5-10H2,1,3-4H3/t16-,17+/m0/s1

> <INCHI_KEY>
WDXXEUARVHTWQF-DLBZAZTESA-N

> <FORMULA>
C21H28O3

> <MOLECULAR_WEIGHT>
328.452

> <EXACT_MASS>
328.203844762

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
52

> <JCHEM_AVERAGE_POLARIZABILITY>
38.402090290797396

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1'R,6'R)-6-hydroxy-3'-methyl-4-pentyl-6'-(prop-1-en-2-yl)-[1,1'-bi(cyclohexane)]-1(6),2',3-triene-2,5-dione

> <JCHEM_LOGP>
5.228800284000001

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.166102016130402

> <JCHEM_PKA_STRONGEST_BASIC>
-5.031206978144391

> <JCHEM_POLAR_SURFACE_AREA>
54.37

> <JCHEM_REFRACTIVITY>
100.1391

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(1'R,6'R)-6-hydroxy-3'-methyl-4-pentyl-6'-(prop-1-en-2-yl)-[1,1'-bi(cyclohexane)]-1(6),2',3-triene-2,5-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 14-JAN-23   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   14-JAN-23         0                                  
HETATM    1  O   UNK     0      -4.001 -11.550   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      -4.001 -10.010   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.667  -9.240   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.667  -7.700   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.334  -6.930   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000  -7.700   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.667  -7.700   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -4.001  -6.930   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -5.335  -7.700   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -6.668  -6.930   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0      -1.334 -10.010   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      -5.335  -9.240   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -6.668 -10.010   0.000  0.00  0.00           C+0
HETATM   16  H   UNK     0      -6.668  -8.470   0.000  0.00  0.00           H+0
HETATM   17  C   UNK     0      -6.668 -11.550   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -5.335 -12.320   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -5.335 -13.860   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -3.803 -12.481   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -8.002 -12.320   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -9.336 -11.550   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -9.336 -10.010   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0     -10.669  -9.240   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -8.002  -9.240   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   14                                                  
CONECT    3    2    4   13                                                  
CONECT    4    3    5   10                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8                                                            
CONECT   10    4   11                                                       
CONECT   11   10   12   14                                                  
CONECT   12   11                                                            
CONECT   13    3                                                            
CONECT   14    2   11   15                                                  
CONECT   15   14   16   17   25                                             
CONECT   16   15                                                            
CONECT   17   15   18   21                                                  
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18                                                            
CONECT   21   17   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   15                                                       
MASTER        0    0    0    0    0    0    0    0   25    0   52    0
END

View in JSmol

Synonyms

Value	Source
CBDHQ	MeSH

Chemical Formula

C₂₁H₂₈O₃

Average Mass

328.4520 Da

Monoisotopic Mass

328.20384 Da

IUPAC Name

(1'R,6'R)-6-hydroxy-3'-methyl-4-pentyl-6'-(prop-1-en-2-yl)-[1,1'-bi(cyclohexane)]-1(6),2',3-triene-2,5-dione

Traditional Name

(1'R,6'R)-6-hydroxy-3'-methyl-4-pentyl-6'-(prop-1-en-2-yl)-[1,1'-bi(cyclohexane)]-1(6),2',3-triene-2,5-dione

CAS Registry Number

Not Available

SMILES

[H][C@]1(C=C(C)CC[C@H]1C(C)=C)C1=C(O)C(=O)C(CCCCC)=CC1=O

InChI Identifier

InChI=1S/C21H28O3/c1-5-6-7-8-15-12-18(22)19(21(24)20(15)23)17-11-14(4)9-10-16(17)13(2)3/h11-12,16-17,24H,2,5-10H2,1,3-4H3/t16-,17+/m0/s1

InChI Key

WDXXEUARVHTWQF-DLBZAZTESA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
HSQC NMR	[¹H, ¹³C] NMR Spectrum (2D, 400 MHz, CDCl3, experimental)	alessio.porta@unipv.it	University of Pavia	Alessio Porta	2024-05-02	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, CDCl3, experimental)	alessio.porta@unipv.it	University of Pavia	Alessio Porta	2024-05-02	View Spectrum
1D_DEPT NMR	¹³C NMR Spectrum (1D, 101 MHz, CDCl3, experimental)	alessio.porta@unipv.it	University of Pavia	Alessio Porta	2024-05-02	View Spectrum
COSY NMR	[¹H, ¹H] NMR Spectrum (2D, 400 MHz, CDCl3, experimental)	alessio.porta@unipv.it	University of Pavia	Alessio Porta	2024-05-02	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CDCl3, experimental)	alessio.porta@unipv.it	University of Pavia	Alessio Porta	2024-05-02	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
sp.		Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as prenylquinones. These are quinones with a structure characterized by the quinone ring substituted by an prenyl side-chain.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Quinone and hydroquinone lipids

Direct Parent

Prenylquinones

Alternative Parents

Substituents

Prenylbenzoquinone
Monocyclic monoterpenoid
Monoterpenoid
P-menthane monoterpenoid
Quinone
P-benzoquinone
Vinylogous acid
Cyclic ketone
Ketone
Enol
Organic oxygen compound
Organooxygen compound
Carbonyl group
Hydrocarbon derivative
Organic oxide
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic 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	5.23	ChemAxon
pKa (Strongest Acidic)	6.17	ChemAxon
pKa (Strongest Basic)	-5	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	54.37 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	100.14 m³·mol⁻¹	ChemAxon
Polarizability	38.4 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	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

9568213

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11393311

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Schwarzenberg A, Carpenter H, Wright C, Bayazeid O, Brokl M: Characterizing the degradation of cannabidiol in an e-liquid formulation. Sci Rep. 2022 Nov 21;12(1):20058. doi: 10.1038/s41598-022-23910-6. [PubMed:36414659 ]
Wu HY, Jan TR: Cannabidiol hydroxyquinone-induced apoptosis of splenocytes is mediated predominantly by thiol depletion. Toxicol Lett. 2010 May 19;195(1):68-74. doi: 10.1016/j.toxlet.2010.02.012. Epub 2010 Feb 23. [PubMed:20184945 ]
Kogan NM, Blazquez C, Alvarez L, Gallily R, Schlesinger M, Guzman M, Mechoulam R: A cannabinoid quinone inhibits angiogenesis by targeting vascular endothelial cells. Mol Pharmacol. 2006 Jul;70(1):51-9. doi: 10.1124/mol.105.021089. Epub 2006 Mar 29. [PubMed:16571653 ]

Capucciati A, Casali E, Bini A, Doria F, Merli D, Porta A: Easy and Accessible Synthesis of Cannabinoids from CBD. J Nat Prod. 2024 Apr 26;87(4):869-875. doi: 10.1021/acs.jnatprod.3c01117. Epub 2024 Mar 1. [PubMed:38427968 ]

Showing NP-Card for CBDQ (NP0332906)

MOL for NP0332906 (CBDQ)

3D MOL for NP0332906 (CBDQ)

3D SDF for NP0332906 (CBDQ)

3D-SDF for NP0332906 (CBDQ)

PDB for NP0332906 (CBDQ)

3D PDB for NP0332906 (CBDQ)

SMILES for NP0332906 (CBDQ)

INCHI for NP0332906 (CBDQ)

Structure for NP0332906 (CBDQ)

3D Structure for NP0332906 (CBDQ)