NP-MRD: Showing NP-Card for Cannabidiolic acid (NP0044836)

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Record Information

Version

2.0

Created at

2022-03-10 18:36:20 UTC

Updated at

2022-03-10 22:18:58 UTC

NP-MRD ID

NP0044836

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Cannabidiolic acid

Description

Cannabidiolic acid (CBDA) 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, at least, one hydroxyl group. CBDA also belongs to the class of cannabis compounds known as cannabidiol. The biosynthesis of CBDA occurs through the cyclization of the isoprenoid side chain of cannabigerolic acid (CBGA) to yield a cyclohexene moiety, common to all cannabidiol-type cannabinoids. CBDA is one of the major cannabinoid compounds found in cannabis plants, particularly in the fiber-type varieties. Even though CBDA is a non-psychoactive component of Cannabis sativa, it has been proven to inhibit the migration of the highly invasive human breast cancer cell line MDA-MB-231. The apparent mechanism of action involves the inhibition of cAMP-dependent protein kinase A and the activation of Ras homolog family member A (RhoA; PMID: 22963825 ). Studies on mice have also shown that CBDA has a potential anticonvulsant activity (PMID: 31686510 ).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309272007292D          

 26 27  0  0  0  0            999 V2000
10000.715610001.0941    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10002.1429 9998.6193    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9999.285510000.2691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.5710 9999.8558    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9999.285510001.0941    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9999.2855 9998.6193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.5710 9999.0308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.8566 9998.6193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.1421 9999.0308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.4277 9998.6193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.8586 9998.1888    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.1429 9997.7753    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.5701 9997.7753    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.858610002.3316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.4294 9999.8561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.715010000.2686    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.0005 9999.8560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.0004 9999.0311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.7149 9998.6186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.4295 9999.0311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.857910001.5065    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.143410001.0940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.143410000.2689    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10002.8579 9999.8565    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10003.572410000.2689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.572410001.0940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  3  4  1  0  0  0  0
  3  5  2  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
  9 10  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  2  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 15  1  0  0  0  0
 17  3  1  0  0  0  0
 18  6  1  0  0  0  0
 20  2  1  0  0  0  0
  1 16  1  0  0  0  0
 21 22  2  0  0  0  0
 21 26  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 21 14  1  0  0  0  0
 24 11  1  1  0  0  0
 23 15  1  6  0  0  0
M  END

     RDKit          3D

 56 57  0  0  0  0  0  0  0  0999 V2000
   -5.7602    1.1895    0.0363 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5250    1.5113   -0.1278 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1156    2.8766    0.3499 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4106    0.6705   -0.7211 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.0160   -0.5303   -1.3016 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2171   -1.7073   -0.4331 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3620   -1.6456    0.7762 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5300   -2.8743    1.6817 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5459   -0.7001    1.0897 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2925    0.5720    0.2486 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9269    0.3266   -0.2548 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4752   -0.7838   -0.9067 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3293   -1.7596   -1.3328 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8942   -0.9664   -1.1527 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8298   -0.0459   -0.7538 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2918   -0.3823   -0.9645 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8366   -0.9258    0.3279 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2836   -1.2410    0.2425 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0800   -0.0185   -0.1289 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5601   -0.3518   -0.1601 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3939    1.0827   -0.0984 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3895    2.1308    0.2068 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6237    2.0108   -0.0086 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9655    3.3279    0.7657 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0668    1.2683    0.1490 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4320    2.3518    0.7937 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2172    0.2566   -0.2248 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4671    1.9208    0.4743 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0125    3.5242    0.5435 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4391    3.2954   -0.4164 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6168    2.7980    1.3398 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9897    1.2711   -1.6004 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0586   -0.2360   -1.6731 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4695   -0.8617   -2.2507 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9915   -2.6251   -1.0559 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2575   -1.8775   -0.0613 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5410   -2.9019    2.1213 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5232   -3.7552    0.9629 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6984   -2.9817    2.3746 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9629   -0.7351    2.0030 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3517    1.3856    0.9741 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0044   -2.5770   -1.7928 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2145   -1.8652   -1.6703 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3038   -1.2687   -1.6726 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8754    0.3977   -1.4094 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6086   -0.2644    1.2053 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2440   -1.9001    0.4869 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6764   -1.6669    1.1958 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4162   -2.0013   -0.5871 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8265    0.3127   -1.1721 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9023    0.7978    0.5903 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0262    0.2758   -0.9459 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0001    0.0260    0.8097 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6898   -1.4171   -0.3038 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5835    4.1497    0.7550 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0433    3.1369    1.1732 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 21  2  0
 21 22  1  0
 22 24  1  0
 22 23  2  0
 21 25  1  0
 25 26  1  0
 25 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 12  1  0
 12 13  1  0
 12 14  2  0
 14 15  1  0
  4 10  1  0
 20 52  1  0
 20 53  1  0
 20 54  1  0
 19 50  1  0
 19 51  1  0
 18 48  1  0
 18 49  1  0
 17 46  1  0
 17 47  1  0
 16 44  1  0
 16 45  1  0
 24 55  1  0
 26 56  1  0
 10 41  1  1
  9 40  1  0
  8 37  1  0
  8 38  1  0
  8 39  1  0
  6 35  1  0
  6 36  1  0
  5 33  1  0
  5 34  1  0
  4 32  1  6
  3 29  1  0
  3 30  1  0
  3 31  1  0
  1 27  1  0
  1 28  1  0
 13 42  1  0
 14 43  1  0
M  END


  Mrv1652309272007292D          

 26 27  0  0  0  0            999 V2000
10000.715610001.0941    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10002.1429 9998.6193    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9999.285510000.2691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.5710 9999.8558    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9999.285510001.0941    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9999.2855 9998.6193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.5710 9999.0308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.8566 9998.6193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.1421 9999.0308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.4277 9998.6193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.8586 9998.1888    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.1429 9997.7753    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.5701 9997.7753    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.858610002.3316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.4294 9999.8561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.715010000.2686    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.0005 9999.8560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.0004 9999.0311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.7149 9998.6186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.4295 9999.0311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.857910001.5065    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.143410001.0940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.143410000.2689    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10002.8579 9999.8565    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10003.572410000.2689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.572410001.0940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  3  4  1  0  0  0  0
  3  5  2  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
  9 10  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  2  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 15  1  0  0  0  0
 17  3  1  0  0  0  0
 18  6  1  0  0  0  0
 20  2  1  0  0  0  0
  1 16  1  0  0  0  0
 21 22  2  0  0  0  0
 21 26  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 21 14  1  0  0  0  0
 24 11  1  1  0  0  0
 23 15  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0044836

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C22H30O4/c1-5-6-7-8-15-12-18(23)20(21(24)19(15)22(25)26)17-11-14(4)9-10-16(17)13(2)3/h11-12,16-17,23-24H,2,5-10H2,1,3-4H3,(H,25,26)/t16-,17+/m0/s1

> <INCHI_KEY>
WVOLTBSCXRRQFR-DLBZAZTESA-N

> <FORMULA>
C22H30O4

> <MOLECULAR_WEIGHT>
358.478

> <EXACT_MASS>
358.214409446

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
56

> <JCHEM_AVERAGE_POLARIZABILITY>
41.04557178941927

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2,4-dihydroxy-3-[(1R,6R)-3-methyl-6-(prop-1-en-2-yl)cyclohex-2-en-1-yl]-6-pentylbenzoic acid

> <ALOGPS_LOGP>
4.55

> <JCHEM_LOGP>
6.632784034666669

> <ALOGPS_LOGS>
-4.00

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
9.665815616418845

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.9122612432924897

> <JCHEM_PKA_STRONGEST_BASIC>
-5.825197843384342

> <JCHEM_POLAR_SURFACE_AREA>
77.75999999999999

> <JCHEM_REFRACTIVITY>
105.78709999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.55e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
cannabidiolic acid

> <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    8668.0028668.709   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0    8670.6678664.089   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0    8665.3338667.169   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0    8663.9998666.397   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0    8665.3338668.709   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0    8665.3338664.089   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0    8663.9998664.857   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    8662.6668664.089   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8661.3328664.857   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8659.9988664.089   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8672.0038663.286   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8670.6678662.514   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8673.3318662.514   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8672.0038671.019   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8669.3358666.398   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    8668.0018667.168   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0    8666.6688666.398   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0    8666.6678664.858   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0    8668.0018664.088   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0    8669.3358664.858   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0    8672.0018669.479   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0    8670.6688668.709   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0    8670.6688667.169   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0    8672.0018666.399   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0    8673.3358667.169   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0    8673.3358668.709   0.000  0.00  0.00           C+0
CONECT    1   16                                                            
CONECT    2   20                                                            
CONECT    3    4    5   17                                                  
CONECT    4    3                                                            
CONECT    5    3                                                            
CONECT    6    7   18                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9                                                            
CONECT   11   12   13   24                                                  
CONECT   12   11                                                            
CONECT   13   11                                                            
CONECT   14   21                                                            
CONECT   15   16   20   23                                                  
CONECT   16   15   17    1                                                  
CONECT   17   16   18    3                                                  
CONECT   18   17   19    6                                                  
CONECT   19   18   20                                                       
CONECT   20   19   15    2                                                  
CONECT   21   22   26   14                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24   15                                                  
CONECT   24   23   25   11                                                  
CONECT   25   24   26                                                       
CONECT   26   21   25                                                       
MASTER        0    0    0    0    0    0    0    0   26    0   54    0
END

View in JSmol

Synonyms

Value	Source
3-p-Mentha-1,8-dien-3-yl-6-pentyl-beta-resorcylic acid	ChEBI
CBDA	ChEBI
Cannabidiolate	Kegg
3-p-Mentha-1,8-dien-3-yl-6-pentyl-b-resorcylate	Generator
3-p-Mentha-1,8-dien-3-yl-6-pentyl-b-resorcylic acid	Generator
3-p-Mentha-1,8-dien-3-yl-6-pentyl-beta-resorcylate	Generator
3-p-Mentha-1,8-dien-3-yl-6-pentyl-β-resorcylate	Generator
3-p-Mentha-1,8-dien-3-yl-6-pentyl-β-resorcylic acid	Generator
Cannabidiol acid	PhytoBank
Cannabidiolcarboxylic acid	PhytoBank

Chemical Formula

C₂₂H₃₀O₄

Average Mass

358.4780 Da

Monoisotopic Mass

358.21441 Da

IUPAC Name

2,4-dihydroxy-3-[(1R,6R)-3-methyl-6-(prop-1-en-2-yl)cyclohex-2-en-1-yl]-6-pentylbenzoic acid

Traditional Name

cannabidiolic acid

CAS Registry Number

1244-58-2

SMILES

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

InChI Identifier

InChI=1S/C22H30O4/c1-5-6-7-8-15-12-18(23)20(21(24)19(15)22(25)26)17-11-14(4)9-10-16(17)13(2)3/h11-12,16-17,23-24H,2,5-10H2,1,3-4H3,(H,25,26)/t16-,17+/m0/s1

InChI Key

WVOLTBSCXRRQFR-DLBZAZTESA-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 inflorescences	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 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
Aromatic monoterpenoid
P-menthane monoterpenoid
Salicylic acid
Salicylic acid or derivatives
Hydroxybenzoic acid
Monoterpenoid
Monocyclic monoterpenoid
Benzoic acid
Benzoyl
Resorcinol
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Vinylogous acid
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Hydrocarbon derivative
Organic oxygen compound
Organooxygen compound
Organic oxide
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

resorcinols (CHEBI:3359 )
polyketide (CHEBI:3359 )
dihydroxybenzoic acid (CHEBI:3359 )
phytocannabinoid (CHEBI:3359 )
Other aromatic polyketides (C10784 )
Other aromatic polyketides (LMPK13120003 )

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	4.55	ALOGPS
logP	6.63	ChemAxon
logS	-4	ALOGPS
pKa (Strongest Acidic)	2.91	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	7	ChemAxon
Refractivity	105.79 m³·mol⁻¹	ChemAxon
Polarizability	41.05 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

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00002642

Chemspider ID

Not Available

KEGG Compound ID

C10784

BioCyc ID

CPD-7170

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

160570

PDB ID

Not Available

ChEBI ID

3359

Good Scents ID

Not Available

References

General References

Takeda S, Okajima S, Miyoshi H, Yoshida K, Okamoto Y, Okada T, Amamoto T, Watanabe K, Omiecinski CJ, Aramaki H: Cannabidiolic acid, a major cannabinoid in fiber-type cannabis, is an inhibitor of MDA-MB-231 breast cancer cell migration. Toxicol Lett. 2012 Nov 15;214(3):314-9. doi: 10.1016/j.toxlet.2012.08.029. Epub 2012 Sep 8. [PubMed:22963825 ]
Anderson LL, Low IK, Banister SD, McGregor IS, Arnold JC: Pharmacokinetics of Phytocannabinoid Acids and Anticonvulsant Effect of Cannabidiolic Acid in a Mouse Model of Dravet Syndrome. J Nat Prod. 2019 Nov 22;82(11):3047-3055. doi: 10.1021/acs.jnatprod.9b00600. Epub 2019 Nov 5. [PubMed:31686510 ]
Taura F, Sirikantaramas S, Shoyama Y, Yoshikai K, Shoyama Y, Morimoto S: Cannabidiolic-acid synthase, the chemotype-determining enzyme in the fiber-type Cannabis sativa. FEBS Lett. 2007 Jun 26;581(16):2929-34. doi: 10.1016/j.febslet.2007.05.043. Epub 2007 May 25. [PubMed:17544411 ]

Showing NP-Card for Cannabidiolic acid (NP0044836)

MOL for NP0044836 (Cannabidiolic acid)

3D MOL for NP0044836 (Cannabidiolic acid)

3D SDF for NP0044836 (Cannabidiolic acid)

3D-SDF for NP0044836 (Cannabidiolic acid)

PDB for NP0044836 (Cannabidiolic acid)

3D PDB for NP0044836 (Cannabidiolic acid)

SMILES for NP0044836 (Cannabidiolic acid)

INCHI for NP0044836 (Cannabidiolic acid)

Structure for NP0044836 (Cannabidiolic acid)

3D Structure for NP0044836 (Cannabidiolic acid)