NP-MRD: Showing NP-Card for Cannabidiol (NP0044828)

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Record Information

Version

2.0

Created at

2022-03-10 18:31:33 UTC

Updated at

2022-03-10 22:18:52 UTC

NP-MRD ID

NP0044828

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Cannabidiol

Description

Cannabidiol (CBD) is one of at least 85 active cannabinoids identified within the Cannabis plant. It is a major phytocannabinoid, accounting for up to 40% of the Cannabis plant's extract, that binds to a wide variety of physiological targets of the endocannabinoid system within the body. Although the exact medical implications are currently being investigated, CBD has shown promise as a therapeutic and pharmaceutical drug target as an analgesic, anticonvulsant, muscle relaxant, anxiolytic, antipsychotic and has shown neuroprotective, anti-inflammatory, and antioxidant activity, among other currently investigated uses (PMID: 26218440 ; PMID: 17828291 ). CBD's exact place within medical practice is still currently hotly debated. However as the body of evidence grows and legislation changes to reflect its wide-spread use, public and medical opinion have changed significantly with regards to its usefulness in a number of medical conditions ranging from anxiety to epilepsy. From a pharmacological perspective, Cannabis' (and CBD's) diverse receptor profile explains its potential application for such a wide variety of medical conditions. Cannabis contains more than 400 different chemical compounds, of which 61 are considered cannabinoids (PMID: 23408483 ). Cannabinoid receptors are utilized endogenously by the body through the endocannabinoid system, which includes a group of lipid proteins, enzymes, and receptors that are involved in many physiological processes. Through its modulation of neurotransmitter release, the endocannabinoid system regulates cognition, pain sensation, appetite, memory, sleep, immune function, and mood among many other bodily systems. These effects are largely mediated through two members of the G-protein coupled receptors family, cannabinoid receptors 1 and 2 (CB1 and CB2) (PMID: 26015168 ; PMID: 29533978 ). CB1 receptors are found in both the central and peripheral nervous systems, with most receptors localized to the hippocampus and amygdala of the brain. Physiological effects of using cannabis make sense in the context of its receptor activity as the hippocampus and amygdala are primarily involved with regulation of memory, fear, and emotion. In contrast, CB2 receptors are mainly found peripherally in immune cells, lymphoid tissue, and peripheral nerve terminals (PMID: 27086601 ). Tetrahydrocannabinol (THC) and cannabidiol (CBD) are two types of cannabinoids found naturally in the resin of the marijuana plant, both of which interact with the cannabinoid receptors that are found throughout the body. Although THC and CBD have been the most studied cannabinoids, there are many others identified to date including cannabinol (CBN), cannabigerol (CBG), Cannabidivarin (CBDV), and Tetrahydrocannabivarin (THCV) that can be found within the medical cannabis (PMID: 16199061 ). While both CBD and THC are used for medicinal purposes, they have different receptor activity, function, and physiological effects. If not provided in their activated form (such as through synthetic forms of THC like Dronabinol or Nabilone), THC and CBD are obtained through conversion from their precursors, tetrahydrocannabinolic acid-A (THCA-A) and cannabidiolic acid (CBDA), through decarboxylation reactions. This can be achieved through heating, smoking, vaporization, or baking of dried unfertilized female cannabis flowers. The primary psychoactive component of Cannabis, delta 9-tetrahydrocannabinol (≈í√Æ9-THC), demonstrates its effects through weak partial agonist activity at Cannabinoid-1 (CB1R) and Cannabinoid-2 (CB2R) receptors. This activity results in the well-known effects of smoking cannabis such as increased appetite, reduced pain, and changes in emotional and cognitive processes. In contrast to THC's weak agonist activity, CBD has been shown to act as a negative allosteric modulator of the CB1 receptor, the most abundant G-Protein Coupled Receptor (GPCR) in the body (PMID: 26218440 ). Allosteric regulation is achieved through the modulation of receptor activity on a functionally distinct site from the agonist or antagonist binding site which is clinically significant as direct agonists (such as THC) are limited by their psychomimetic effects such as changes to mood, memory, and anxiety (PMID: 26218440 ). In addition to the well-known activity on CB1 and CB2 receptors, there is further evidence that CBD also activates serotonin Type 1A, 2A,3A (HT1A/2A/3A) serotonergic and transient receptor potential cation channel subfamily V member 2 receptors (TRPV1‚Äö√Ñ√¨2) vanilloid receptors, antagonizes alpha-1 adrenergic and ¬¨¬µ-opioid receptors, inhibits synaptosomal uptake of noradrenaline, dopamine, serotonin and gamma-aminobutyric acid (GABA), and cellular uptake of anandamide, acts on mitochondria Ca2+ stores, blocks low-voltage-activated (T-type) Ca2+ channels, stimulates activity of the inhibitory glycine-receptor, and inhibits activity of fatty amide hydrolase (FAAH) (PMID: 26264914 ; PMID: 24281562 ). CBD is currently available in Canada within a 1:1 Formulation with tetrahydrocannbinol (THC) (as the formulation known as "nabiximols"; as the brand name product Sativex). It is approved for use as adjunctive treatment for symptomatic relief of spasticity in adult patients with multiple sclerosis (MS). Sativex was also given a conditional Notice of Compliance (NOC/c) for use as adjunctive treatment for the symptomatic relief of neuropathic pain in adult patients with multiple sclerosis and as adjunctive analgesic treatment for moderate to severe pain in adult patients with advanced cancer. In April 2018, a Food and Drug Administration advisory panel unanimously recommended approval of Epidiolex (cannabidiol oral solution) for the treatment of two rare forms of epilepsy - Lennox-Gastaut syndrome and Dravet syndrome, which are among the two most difficult types of epilepsy to treat. Epidiolex was granted Orphan Drug designation as well as Fast Track Approval from the FDA for further study in these hard to treat conditions. Notably, phase 3 clinical trials of Epidiolex have demonstrated clinically significant improvement in Lennox-Gastaut syndrome and Dravet syndrome. On June 25th, 2018, Epidiolex was approved by the FDA to be the first CBD-based product available on the US market.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 53 54  0  0  0  0  0  0  0  0999 V2000
   -3.3595   -2.0281   -1.9131 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0879   -1.8979   -0.6467 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5245   -3.1003    0.2041 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4301   -0.7984    0.0432 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.4828   -0.2487    1.0793 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3199    0.7702    0.3117 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4257    1.9622    0.1823 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8375    3.3214    0.5617 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2246    1.7236   -0.3139 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8713    0.3388   -0.6574 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3592    0.2735   -0.7745 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3947    1.1514   -0.0130 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1692    1.9668    0.9614 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7910    1.2359   -0.2024 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4286    0.4655   -1.1264 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8711    0.4870   -1.2798 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5888   -0.7141   -0.8272 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5319   -1.2441    0.5245 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9872   -0.4732    1.6907 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3135    0.7900    2.0383 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6534   -0.4103   -1.8790 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2587   -0.5151   -1.7117 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4200   -1.4213   -2.5175 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8721   -2.9465   -2.2847 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1343   -1.2798   -2.6753 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9414   -3.9662   -0.1550 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2572   -2.9465    1.2452 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5888   -3.2671    0.0210 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6609   -1.2880    0.7512 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9227    0.2690    1.8628 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1048   -1.0374    1.4689 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2930    0.9715    0.7513 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3893    0.3708   -0.7564 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0550    3.8189    1.2100 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9932    3.9833   -0.2866 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7754    3.2909    1.1752 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5264    2.5609   -0.5037 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2331    0.2472   -1.7650 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2921    2.6100    1.5572 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3118    1.9517    0.4137 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0946    0.6027   -2.4104 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2689    1.3968   -0.8498 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4668   -1.5699   -1.5960 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7021   -0.4729   -1.0230 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5018   -1.7151    0.7594 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1670   -2.2042    0.5239 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8745   -1.1483    2.6049 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0953   -0.2825    1.6824 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2155    0.6418    2.2712 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7214    1.0713    3.0709 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4925    1.6759    1.4383 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1327   -1.0066   -2.6108 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1041   -1.9665   -3.1829 H   0  0  0  0  0  0  0  0  0  0  0  0
 20 19  1  0
 19 18  1  0
 18 17  1  0
 17 16  1  0
 16 15  1  0
 15 14  2  0
 14 12  1  0
 12 13  1  0
 12 11  2  0
 11 10  1  0
 10  9  1  0
  9  7  2  0
  7  8  1  0
  7  6  1  0
  6  5  1  0
  5  4  1  0
  4  2  1  0
  2  3  1  0
  2  1  2  3
 11 22  1  0
 22 23  1  0
 22 21  2  0
 21 15  1  0
  4 10  1  0
 20 49  1  0
 20 50  1  0
 20 51  1  0
 19 47  1  0
 19 48  1  0
 18 45  1  0
 18 46  1  0
 17 43  1  0
 17 44  1  0
 16 41  1  0
 16 42  1  0
 14 40  1  0
 13 39  1  0
 10 38  1  6
  9 37  1  0
  8 34  1  0
  8 35  1  0
  8 36  1  0
  6 32  1  0
  6 33  1  0
  5 30  1  0
  5 31  1  0
  4 29  1  1
  3 26  1  0
  3 27  1  0
  3 28  1  0
  1 24  1  0
  1 25  1  0
 23 53  1  0
 21 52  1  0
M  END


  Mrv1652309272007282D          

 23 24  0  0  0  0            999 V2000
10005.843810006.2223    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10007.271010003.7475    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10004.413710003.7475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.699210004.1590    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.984810003.7475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.270310004.1590    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.555910003.7475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10007.986810003.3170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10007.271010002.9035    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10008.698310002.9035    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10007.986810007.4598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10006.557610004.9844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10005.843210005.3968    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10005.128610004.9843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10005.128510004.1593    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10005.843110003.7468    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10006.557710004.1593    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10007.986110006.6347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10007.271510006.2222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10007.271510005.3971    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10007.986110004.9848    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10008.700610005.3971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10008.700610006.2222    0.0000 C   0  0  0  0  0  0  0  0  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
  8  9  1  0  0  0  0
  8 10  2  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 12  1  0  0  0  0
 15  3  1  0  0  0  0
 17  2  1  0  0  0  0
  1 13  1  0  0  0  0
 18 19  2  0  0  0  0
 18 23  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 18 11  1  0  0  0  0
 21  8  1  1  0  0  0
 20 12  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0044828

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCCCC1=CC(O)=C([C@@H]2C=C(C)CC[C@H]2C(C)=C)C(O)=C1

> <INCHI_IDENTIFIER>
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

> <INCHI_KEY>
QHMBSVQNZZTUGM-ZWKOTPCHSA-N

> <FORMULA>
C21H30O2

> <MOLECULAR_WEIGHT>
314.469

> <EXACT_MASS>
314.224580206

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
53

> <JCHEM_AVERAGE_POLARIZABILITY>
38.26369097866226

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-[(1R,6R)-3-methyl-6-(prop-1-en-2-yl)cyclohex-2-en-1-yl]-5-pentylbenzene-1,3-diol

> <ALOGPS_LOGP>
6.10

> <JCHEM_LOGP>
6.325201126666667

> <ALOGPS_LOGS>
-4.40

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
10.58381154908063

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.12873016538115

> <JCHEM_PKA_STRONGEST_BASIC>
-5.723975042887205

> <JCHEM_POLAR_SURFACE_AREA>
40.46

> <JCHEM_REFRACTIVITY>
98.53089999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.26e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
cannabidiol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 27-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-SEP-20         0                                  
HETATM    1  O   UNK     0    8677.5758678.282   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0    8680.2398673.662   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0    8674.9068673.662   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0    8673.5728674.430   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0    8672.2388673.662   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0    8670.9058674.430   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0    8669.5718673.662   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    8681.5758672.858   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8680.2398672.087   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8682.9038672.087   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8681.5758680.592   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8678.9078675.971   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8677.5748676.741   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8676.2408675.971   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8676.2408674.431   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    8677.5748673.661   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0    8678.9088674.431   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0    8681.5748679.051   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0    8680.2408678.281   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0    8680.2408676.741   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0    8681.5748675.972   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0    8682.9088676.741   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0    8682.9088678.281   0.000  0.00  0.00           C+0
CONECT    1   13                                                            
CONECT    2   17                                                            
CONECT    3    4   15                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6                                                            
CONECT    8    9   10   21                                                  
CONECT    9    8                                                            
CONECT   10    8                                                            
CONECT   11   18                                                            
CONECT   12   13   17   20                                                  
CONECT   13   12   14    1                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16    3                                                  
CONECT   16   15   17                                                       
CONECT   17   16   12    2                                                  
CONECT   18   19   23   11                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21   12                                                  
CONECT   21   20   22    8                                                  
CONECT   22   21   23                                                       
CONECT   23   18   22                                                       
MASTER        0    0    0    0    0    0    0    0   23    0   48    0
END

View in JSmol

Synonyms

Value	Source
(-)-Cannabidiol	ChEBI
(-)-CBD	ChEBI
(-)-trans-2-p-Mentha-1,8-dien-3-yl-5-pentylresorcinol	ChEBI
(-)-trans-Cannabidiol	ChEBI
Cannabidiolum	ChEBI
Delta(1(2))-trans-Cannabidiol	ChEBI
Δ(1(2))-trans-cannabidiol	Generator
CBD	ChEMBL
Cannabidiol	MeSH
Epidiolex	PhytoBank
delta1(2)-trans-Cannabidiol	PhytoBank
Δ1(2)-trans-Cannabidiol	PhytoBank

Chemical Formula

C₂₁H₃₀O₂

Average Mass

314.4690 Da

Monoisotopic Mass

314.22458 Da

IUPAC Name

2-[(1R,6R)-3-methyl-6-(prop-1-en-2-yl)cyclohex-2-en-1-yl]-5-pentylbenzene-1,3-diol

Traditional Name

cannabidiol

CAS Registry Number

3556-78-3

SMILES

CCCCCC1=CC(O)=C([C@@H]2C=C(C)CC[C@H]2C(C)=C)C(O)=C1

InChI Identifier

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

InChI Key

QHMBSVQNZZTUGM-ZWKOTPCHSA-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 indica	Plant	KNApSAcK
Cannabis sativa	NULL	Not Available
Cannabis sativa var. indica	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as aromatic monoterpenoids. These are monoterpenoids containing at least one aromatic ring.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Monoterpenoids

Direct Parent

Aromatic monoterpenoids

Alternative Parents

Substituents

P-menthane monoterpenoid
Monocyclic monoterpenoid
Aromatic monoterpenoid
Resorcinol
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Benzenoid
Monocyclic benzene moiety
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

organic molecular entity (CHEBI:69478 )

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	6.1	ALOGPS
logP	6.33	ChemAxon
logS	-4.4	ALOGPS
pKa (Strongest Acidic)	9.13	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	6	ChemAxon
Refractivity	98.53 m³·mol⁻¹	ChemAxon
Polarizability	38.26 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

DB09061

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00002641

Chemspider ID

559095

KEGG Compound ID

Not Available

BioCyc ID

CPD-7173

BiGG ID

Not Available

Wikipedia Link

Cannabidiol

METLIN ID

Not Available

PubChem Compound

644019

PDB ID

Not Available

ChEBI ID

69478

Good Scents ID

Not Available

References

General References

Burstein S: Cannabidiol (CBD) and its analogs: a review of their effects on inflammation. Bioorg Med Chem. 2015 Apr 1;23(7):1377-85. doi: 10.1016/j.bmc.2015.01.059. Epub 2015 Feb 7. [PubMed:25703248 ]
Campos AC, Fogaca MV, Sonego AB, Guimaraes FS: Cannabidiol, neuroprotection and neuropsychiatric disorders. Pharmacol Res. 2016 Oct;112:119-127. doi: 10.1016/j.phrs.2016.01.033. Epub 2016 Feb 1. [PubMed:26845349 ]
Leo A, Russo E, Elia M: Cannabidiol and epilepsy: Rationale and therapeutic potential. Pharmacol Res. 2016 May;107:85-92. doi: 10.1016/j.phrs.2016.03.005. Epub 2016 Mar 11. [PubMed:26976797 ]
Parray HA, Yun JW: Cannabidiol promotes browning in 3T3-L1 adipocytes. Mol Cell Biochem. 2016 May;416(1-2):131-9. doi: 10.1007/s11010-016-2702-5. Epub 2016 Apr 11. [PubMed:27067870 ]
Soares VP, Campos AC: Evidences for the Anti-panic Actions of Cannabidiol. Curr Neuropharmacol. 2017;15(2):291-299. doi: 10.2174/1570159x14666160509123955. [PubMed:27157263 ]
Laprairie RB, Bagher AM, Kelly ME, Denovan-Wright EM: Cannabidiol is a negative allosteric modulator of the cannabinoid CB1 receptor. Br J Pharmacol. 2015 Oct;172(20):4790-805. doi: 10.1111/bph.13250. Epub 2015 Oct 13. [PubMed:26218440 ]
Pertwee RG: The diverse CB1 and CB2 receptor pharmacology of three plant cannabinoids: delta9-tetrahydrocannabinol, cannabidiol and delta9-tetrahydrocannabivarin. Br J Pharmacol. 2008 Jan;153(2):199-215. doi: 10.1038/sj.bjp.0707442. Epub 2007 Sep 10. [PubMed:17828291 ]
Baron EP: Comprehensive Review of Medicinal Marijuana, Cannabinoids, and Therapeutic Implications in Medicine and Headache: What a Long Strange Trip It's Been .... Headache. 2015 Jun;55(6):885-916. doi: 10.1111/head.12570. Epub 2015 May 25. [PubMed:26015168 ]
Kaur R, Ambwani SR, Singh S: Endocannabinoid System: A Multi-Facet Therapeutic Target. Curr Clin Pharmacol. 2016;11(2):110-7. doi: 10.2174/1574884711666160418105339. [PubMed:27086601 ]
Ibeas Bih C, Chen T, Nunn AV, Bazelot M, Dallas M, Whalley BJ: Molecular Targets of Cannabidiol in Neurological Disorders. Neurotherapeutics. 2015 Oct;12(4):699-730. doi: 10.1007/s13311-015-0377-3. [PubMed:26264914 ]
Zhornitsky S, Potvin S: Cannabidiol in humans-the quest for therapeutic targets. Pharmaceuticals (Basel). 2012 May 21;5(5):529-52. doi: 10.3390/ph5050529. [PubMed:24281562 ]

Showing NP-Card for Cannabidiol (NP0044828)

MOL for NP0044828 (Cannabidiol)

3D MOL for NP0044828 (Cannabidiol)

3D SDF for NP0044828 (Cannabidiol)

3D-SDF for NP0044828 (Cannabidiol)

PDB for NP0044828 (Cannabidiol)

3D PDB for NP0044828 (Cannabidiol)

SMILES for NP0044828 (Cannabidiol)

INCHI for NP0044828 (Cannabidiol)

Structure for NP0044828 (Cannabidiol)

3D Structure for NP0044828 (Cannabidiol)