cannabidiol (CHEBI:69478)

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CHEBI:69478 - cannabidiol

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ChEBI Name	cannabidiol

ChEBI ID	CHEBI:69478

Definition	An cannabinoid that is cyclohexene which is substituted by a methyl group at position 1, a 2,6-dihydroxy-4-pentylphenyl group at position 3, and a prop-1-en-2-yl group at position 4.

Stars	This entity has been manually annotated by the ChEBI Team.

Secondary ChEBI IDs	CHEBI:3358

Supplier Information	ChemicalBook:CB6705020, eMolecules:518145, eMolecules:883971, ZINC000006661227

Download	Molfile XML SDF

more structures >>

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The Resolver thinks Mol

P0T - Ideal conformer

Mrv1927 05282122003D

starting HoverWatcher_5

Time for openFile(P0T - Ideal conformer

Mrv1927 05282122003D

53 54 0 0 0 0 999 V2000

-1.9450 2.2860 -0.5700 C 0 0 0 0 0 0 0 0 0 0 0 0

0.0550 0.1810 1.6110 C 0 0 0 0 0 0 0 0 0 0 0 0

-0.2090 -0.9930 -0.4660 C 0 0 0 0 0 0 0 0 0 0 0 0

-4.7890 -2.6940 -0.0200 C 0 0 0 0 0 0 0 0 0 0 0 0

-2.3520 3.1880 0.5670 C 0 0 0 0 0 0 0 0 0 0 0 0

-2.5450 0.9100 -0.6920 C 0 0 1 0 0 0 0 0 0 0 0 0

-2.2210 0.0940 0.5620 C 0 0 1 0 0 0 0 0 0 0 0 0

-4.0690 1.0210 -0.8220 C 0 0 1 0 0 0 0 0 0 0 0 0

-4.6330 -0.3700 -1.1220 C 0 0 1 0 0 0 0 0 0 0 0 0

-3.0240 -1.1730 0.5770 C 0 0 0 0 0 0 0 0 0 0 0 0

-0.7530 -0.2480 0.5690 C 0 0 0 0 0 0 0 0 0 0 0 0

-4.0790 -1.3720 -0.1520 C 0 0 0 0 0 0 0 0 0 0 0 0

1.9460 -0.8780 0.5830 C 0 0 0 0 0 0 0 0 0 0 0 0

1.4060 -0.1360 1.6150 C 0 0 0 0 0 0 0 0 0 0 0 0

1.1430 -1.3080 -0.4560 C 0 0 0 0 0 0 0 0 0 0 0 0

3.4140 -1.2210 0.5900 C 0 0 1 0 0 0 0 0 0 0 0 0

-1.0730 2.7010 -1.4550 C 0 0 0 0 0 0 0 0 0 0 0 0

4.1970 -0.1220 -0.1310 C 0 0 1 0 0 0 0 0 0 0 0 0

5.6870 -0.4700 -0.1230 C 0 0 1 0 0 0 0 0 0 0 0 0

6.4710 0.6290 -0.8440 C 0 0 1 0 0 0 0 0 0 0 0 0

7.9610 0.2810 -0.8370 C 0 0 0 0 0 0 0 0 0 0 0 0

-0.4750 0.9160 2.6240 O 0 0 0 0 0 0 0 0 0 0 0 0

-0.9980 -1.4150 -1.4880 O 0 0 0 0 0 0 0 0 0 0 0 0

-4.3690 -3.4050 -0.7310 H 0 0 0 0 0 0 0 0 0 0 0 0

-4.6620 -3.0750 0.9930 H 0 0 0 0 0 0 0 0 0 0 0 0

-5.8510 -2.5590 -0.2270 H 0 0 0 0 0 0 0 0 0 0 0 0

-3.2140 3.7850 0.2660 H 0 0 0 0 0 0 0 0 0 0 0 0

-2.6150 2.5830 1.4340 H 0 0 0 0 0 0 0 0 0 0 0 0

-1.5240 3.8490 0.8210 H 0 0 0 0 0 0 0 0 0 0 0 0

-2.1380 0.4090 -1.5700 H 0 0 0 0 0 0 0 0 0 0 0 0

-2.4590 0.6830 1.4480 H 0 0 0 0 0 0 0 0 0 0 0 0

-4.4910 1.3940 0.1110 H 0 0 0 0 0 0 0 0 0 0 0 0

-4.3180 1.7040 -1.6350 H 0 0 0 0 0 0 0 0 0 0 0 0

-5.7190 -0.3450 -1.0370 H 0 0 0 0 0 0 0 0 0 0 0 0

-4.3570 -0.6600 -2.1360 H 0 0 0 0 0 0 0 0 0 0 0 0

-2.7050 -1.9670 1.2350 H 0 0 0 0 0 0 0 0 0 0 0 0

2.0360 0.1980 2.4270 H 0 0 0 0 0 0 0 0 0 0 0 0

1.5670 -1.8870 -1.2630 H 0 0 0 0 0 0 0 0 0 0 0 0

3.7630 -1.3010 1.6190 H 0 0 0 0 0 0 0 0 0 0 0 0

3.5670 -2.1710 0.0790 H 0 0 0 0 0 0 0 0 0 0 0 0

-0.6460 3.6900 -1.3700 H 0 0 0 0 0 0 0 0 0 0 0 0

-0.7800 2.0550 -2.2690 H 0 0 0 0 0 0 0 0 0 0 0 0

3.8480 -0.0420 -1.1600 H 0 0 0 0 0 0 0 0 0 0 0 0

4.0430 0.8280 0.3800 H 0 0 0 0 0 0 0 0 0 0 0 0

6.0370 -0.5500 0.9060 H 0 0 0 0 0 0 0 0 0 0 0 0

5.8410 -1.4210 -0.6340 H 0 0 0 0 0 0 0 0 0 0 0 0

6.1220 0.7090 -1.8740 H 0 0 0 0 0 0 0 0 0 0 0 0

6.3170 1.5790 -0.3340 H 0 0 0 0 0 0 0 0 0 0 0 0

8.5190 1.0640 -1.3500 H 0 0 0 0 0 0 0 0 0 0 0 0

8.3100 0.2010 0.1920 H 0 0 0 0 0 0 0 0 0 0 0 0

8.1150 -0.6690 -1.3480 H 0 0 0 0 0 0 0 0 0 0 0 0

-0.8070 0.3870 3.3620 H 0 0 0 0 0 0 0 0 0 0 0 0

-1.0510 -0.7940 -2.2270 H 0 0 0 0 0 0 0 0 0 0 0 0

4 12 1 0 0 0 0

21 20 1 0 0 0 0

20 19 1 0 0 0 0

12 9 1 0 0 0 0

12 10 2 0 0 0 0

22 2 1 0 0 0 0

9 8 1 0 0 0 0

10 7 1 0 0 0 0

19 18 1 0 0 0 0

18 16 1 0 0 0 0

14 2 2 0 0 0 0

14 13 1 0 0 0 0

2 11 1 0 0 0 0

16 13 1 0 0 0 0

13 15 2 0 0 0 0

11 7 1 0 0 0 0

11 3 2 0 0 0 0

7 6 1 0 0 0 0

15 3 1 0 0 0 0

8 6 1 0 0 0 0

3 23 1 0 0 0 0

6 1 1 0 0 0 0

1 17 2 3 0 0 0

1 5 1 0 0 0 0

4 24 1 0 0 0 0

4 25 1 0 0 0 0

4 26 1 0 0 0 0

5 27 1 0 0 0 0

5 28 1 0 0 0 0

5 29 1 0 0 0 0

6 30 1 6 0 0 0

7 31 1 1 0 0 0

8 32 1 0 0 0 0

8 33 1 0 0 0 0

9 34 1 0 0 0 0

9 35 1 0 0 0 0

10 36 1 0 0 0 0

14 37 1 0 0 0 0

15 38 1 0 0 0 0

16 39 1 0 0 0 0

16 40 1 0 0 0 0

17 41 1 0 0 0 0

17 42 1 0 0 0 0

18 43 1 0 0 0 0

18 44 1 0 0 0 0

19 45 1 0 0 0 0

19 46 1 0 0 0 0

20 47 1 0 0 0 0

20 48 1 0 0 0 0

21 49 1 0 0 0 0

21 50 1 0 0 0 0

21 51 1 0 0 0 0

22 52 1 0 0 0 0

23 53 1 0 0 0 0

M END): 18 ms

reading 53 atoms

ModelSet: haveSymmetry:false haveUnitcells:false haveFractionalCoord:false

1 model in this collection. Use getProperty "modelInfo" or getProperty "auxiliaryInfo" to inspect them.

Default Van der Waals type for model set to Babel

53 atoms created

ModelSet: not autobonding; use forceAutobond=true to force automatic bond creation

Script completed

Jmol script terminated

Molfile expand

Wikipedia	License
l-DOPA, also known as l-3,4-dihydroxyphenylalanine and used medically as levodopa, is made and used as part of the normal biology of some plants and animals, including humans. Humans, as well as a portion of the other animals that utilize l-DOPA, make it via biosynthesis from the amino acid l-tyrosine. l-DOPA is the precursor to the neurotransmitters dopamine, norepinephrine (noradrenaline), and epinephrine (adrenaline), which are collectively known as catecholamines. Furthermore, l-DOPA itself mediates neurotrophic factor release by the brain and CNS. In some plant families (of the order Caryophyllales), l-DOPA is the central precursor of a biosynthetic pathway that produces a class of pigments called betalains. l-DOPA can be manufactured and in its pure form is sold as a drug with the INNTooltip International Nonproprietary Name levodopa. Trade names include Sinemet, Pharmacopa, Atamet, and Stalevo. As a drug, it is used in the treatment of Parkinson's disease and dopamine-responsive dystonia, as well as restless leg syndrome. l-DOPA has a counterpart with opposite chirality, d-DOPA. As is true for many molecules, the human body produces only one of these isomers (the l-DOPA form). The enantiomeric purity of l-DOPA may be analyzed by determination of the optical rotation or by chiral thin-layer chromatography.
Read full article at Wikipedia

Formula

C21H30O2

Net Charge

Average Mass

314.469

Monoisotopic Mass

314.22458

InChI

InChI=1S/C21H30O2/c1-5-6-7-8-16-12-19(22)21(20(23)13-16)18-11-15(4)9-10-17(18)14(2)3/h11-13,17-18,22-23H,2,5-10H2,1,3-4H3/t17-,18+/m0/s1

InChIKey

QHMBSVQNZZTUGM-ZWKOTPCHSA-N

SMILES

[H][C@]1(CCC(C)=C[C@H]1C1=C(O)C=C(CCCCC)C=C1O)C(C)=C

Metabolite of Species	Details
Cannabis sativa (NCBI:txid3483)	Found in aerial part (BTO:0001658). Acetone extract of Dried, powdered and heated flowered aerial parts See: PubMed

Roles Classification
Biological Role(s):	antimicrobial agent A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans. plant metabolite Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms. metabolite Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites. (via phytocannabinoid ) cannabinoid receptor agonist An agonist that binds to and activates cannabinoid receptors. (via cannabinoid )

View more via ChEBI Ontology

ChEBI Ontology
Outgoing	cannabidiol (CHEBI:69478) has role antimicrobial agent (CHEBI:33281) cannabidiol (CHEBI:69478) has role plant metabolite (CHEBI:76924) cannabidiol (CHEBI:69478) is a olefinic compound (CHEBI:78840) cannabidiol (CHEBI:69478) is a phytocannabinoid (CHEBI:67196) cannabidiol (CHEBI:69478) is a resorcinols (CHEBI:33572)

Incoming	hydroxy-cannabidiol (CHEBI:133048) has functional parent cannabidiol (CHEBI:69478)

IUPAC Name

(1'R,2'R)-5'-methyl-4-pentyl-2'-(prop-1-en-2-yl)-1',2',3',4'-tetrahydrobiphenyl-2,6-diol

INNs	Sources
cannabidiol	WHO MedNet
cannabidiol	WHO MedNet
cannabidiol	WHO MedNet
cannabidiolum	WHO MedNet

Synonyms	Sources
(−)-cannabidiol	ChemIDplus
(−)-CBD	ChemIDplus
(−)-trans-2-p-mentha-1,8-dien-3-yl-5-pentylresorcinol	ChemIDplus
(−)-trans-cannabidiol	ChemIDplus
Δ¹⁽²⁾-trans-cannabidiol	ChemIDplus

Manual Xrefs	Databases
5288	DrugCentral
C00002641	KNApSAcK
C07578	KEGG COMPOUND
Cannabidiol	Wikipedia
CPD-7173	MetaCyc
DB09061	DrugBank
LMPK13120001	LIPID MAPS
P0T	PDBeChem
US2304669	Patent
View more database links

Registry Numbers	Types	Sources
13956-29-1	CAS Registry Number	KEGG COMPOUND
13956-29-1	CAS Registry Number	ChemIDplus
13956-29-1	CAS Registry Number	NIST Chemistry WebBook
2222023	Reaxys Registry Number	Reaxys

Citations	Types	Sources
25703248	PubMed citation	Europe PMC
26845349	PubMed citation	Europe PMC
26976797	PubMed citation	Europe PMC
27067870	PubMed citation	Europe PMC
27157263	PubMed citation	Europe PMC
27215129	PubMed citation	Europe PMC
27267317	PubMed citation	Europe PMC
27285147	PubMed citation	Europe PMC
27344041	PubMed citation	Europe PMC
27374322	PubMed citation	Europe PMC
27430346	PubMed citation	Europe PMC
27471947	PubMed citation	Europe PMC
27506704	PubMed citation	Europe PMC
31566564	PubMed citation	Europe PMC
32144889	PubMed citation	Europe PMC
36868996	PubMed citation	Europe PMC

Last Modified

07 June 2023

CHEBI:69478 - cannabidiol

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