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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2021-09-24 08:37:08 UTC

Update Date

2021-09-24 08:37:10 UTC

HMDB ID

HMDB0304284

Secondary Accession Numbers

None

Metabolite Identification

Common Name

cannabigerolate

Description

Cannabigerolic acid, CBGA, is a phytocannabinoid that belongs to the class of organic compounds known as hydroxybenzoic acid derivatives. CBGA is a dihydroxybenzoic acid derived from olivetolic acid on which the hydrogen at position 3 is substituted by a geranyl group. CBGA is a molecule of mixed biosynthetic origin, in which its aromatic moiety (derived from olivetolic acid) occurs through the polyketide biosynthetic pathway while the prenylated sidechain derives from the MEP pathway of the terpenoids (DOI: 10.1016/B978-0-12-800756-3.00002-8). As such, CBGA can be considered a polyketide, a monoterpenoid and a resorcinol, due to the meta arrangement of its two hydroxyl groups on the benzene ring. CBGA is a key biosynthetic precursor of Delta (9)-tetrahydrocannabinol, the main psychoactive component of Cannabis sativa. As mentioned above, olivetolic acid and geranyl diphosphate are synthesized into CBGA. The CBGA is converted in the plant by CBCA synthase, cannabidiolic acid synthase (CBDA synthase) and tetrahydrocannabinolic acid synthase (THCA synthase) into CBCA, CBDA and tetrahydrocannabinolic acid (THCA).The THCA can be decarboxylated into THC by drying and heating plant material. Therefore, CBGA is an important cannabinoid found in cannabis. Because of its biosynthetic relationship to other psychoactive compounds, many efforts have been addressed to find alternative ways of producing it, particularly in yeast (PMID: 28694184 ) Additionally, cannabigerolic acid has shown antibiotic properties (PMID: 6991645 ).

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI


  Mrv1652307312018212D          

 26 26  0  0  0  0            999 V2000
    0.0000   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7171   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0026   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0026   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.1250    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
    5.7158   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  1  1  0  0  0  0
  6  5  1  0  0  0  0
  7  6  1  0  0  0  0
  9  8  1  0  0  0  0
 10  8  1  0  0  0  0
 11  7  1  0  0  0  0
 12 13  1  4  0  0  0
 15  2  1  0  0  0  0
 15  3  1  0  0  0  0
 15  9  2  0  0  0  0
 16  4  1  0  0  0  0
 16 10  1  0  0  0  0
 16 12  2  0  0  0  0
 17 11  1  0  0  0  0
 17 14  2  0  0  0  0
 18 13  1  0  0  0  0
 19 14  1  0  0  0  0
 19 18  2  0  0  0  0
 20 17  1  0  0  0  0
 21 18  1  0  0  0  0
 21 20  2  0  0  0  0
 22 20  1  0  0  0  0
 23 19  1  0  0  0  0
 24 21  1  0  0  0  0
 25 22  2  0  0  0  0
 26 22  1  0  0  0  0
M  END

HMDB0304284
     RDKit          3D
cannabigerolate
 58 58  0  0  0  0  0  0  0  0999 V2000
   -6.2999    1.5853   -0.9482 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9266    0.2388   -0.9076 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1650   -0.9367   -0.5014 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5833   -1.1047    0.8319 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4891   -0.2698    1.3479 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1875   -0.3692    0.6612 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8570    0.5690   -0.2956 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6927    0.4987   -1.0152 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4028    1.4778   -1.9811 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8257   -0.5258   -0.7862 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4765   -0.6257   -1.5474 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4342    0.3314   -0.9483 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5966   -0.0499   -0.4362 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0220   -1.4699   -0.4280 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4896    0.9773    0.1525 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8014    1.0040   -0.5725 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6764    2.0497    0.0497 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8361    1.6810    0.5671 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7451    2.6723    1.1975 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2786    0.2471    0.5359 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1128   -1.5107    0.1817 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1816   -2.4692    0.3139 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2961   -1.4142    0.8960 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5220   -2.3915    1.9244 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5389   -2.4143    2.6374 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6026   -3.3879    2.1912 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0344    2.0614   -0.0186 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4525    1.5578   -1.6810 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0387    2.3396   -1.4240 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2677    0.0477   -1.9931 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9541    0.2896   -0.3989 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3716   -1.0995   -1.3266 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7992   -1.8841   -0.6811 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2963   -2.2019    0.9170 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4643   -1.0784    1.5782 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7583    0.8349    1.3639 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3345   -0.4707    2.4298 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5156    1.3776   -0.4612 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5580    1.3994   -2.4974 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8264   -1.6740   -1.4233 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2942   -0.3670   -2.5892 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1759    1.3796   -0.9241 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8312   -1.9866   -1.3782 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5208   -2.0368    0.4067 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1101   -1.5617   -0.2148 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5967    0.7223    1.2309 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0104    1.9906    0.1198 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6210    1.3003   -1.6150 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3016    0.0215   -0.5991 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3918    3.0763    0.0871 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2845    2.9901    2.1732 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7527    2.2722    1.3597 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8177    3.5865    0.5706 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2812    0.1317    0.9856 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5040   -0.3396    1.0514 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3311   -0.0908   -0.5271 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0705   -3.2430    0.8428 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4084   -3.7376    3.1204 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
 12 13  2  3
 13 14  1  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  2  3
 18 19  1  0
 18 20  1  0
 10 21  1  0
 21 22  1  0
 21 23  2  0
 23 24  1  0
 24 25  2  0
 24 26  1  0
 23  6  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
  2 30  1  0
  2 31  1  0
  3 32  1  0
  3 33  1  0
  4 34  1  0
  4 35  1  0
  5 36  1  0
  5 37  1  0
  7 38  1  0
  9 39  1  0
 11 40  1  0
 11 41  1  0
 12 42  1  0
 14 43  1  0
 14 44  1  0
 14 45  1  0
 15 46  1  0
 15 47  1  0
 16 48  1  0
 16 49  1  0
 17 50  1  0
 19 51  1  0
 19 52  1  0
 19 53  1  0
 20 54  1  0
 20 55  1  0
 20 56  1  0
 22 57  1  0
 26 58  1  0
M  END


  Mrv1652307312018212D          

 26 26  0  0  0  0            999 V2000
    0.0000   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7171   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0026   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0026   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.1250    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
    5.7158   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  1  1  0  0  0  0
  6  5  1  0  0  0  0
  7  6  1  0  0  0  0
  9  8  1  0  0  0  0
 10  8  1  0  0  0  0
 11  7  1  0  0  0  0
 12 13  1  4  0  0  0
 15  2  1  0  0  0  0
 15  3  1  0  0  0  0
 15  9  2  0  0  0  0
 16  4  1  0  0  0  0
 16 10  1  0  0  0  0
 16 12  2  0  0  0  0
 17 11  1  0  0  0  0
 17 14  2  0  0  0  0
 18 13  1  0  0  0  0
 19 14  1  0  0  0  0
 19 18  2  0  0  0  0
 20 17  1  0  0  0  0
 21 18  1  0  0  0  0
 21 20  2  0  0  0  0
 22 20  1  0  0  0  0
 23 19  1  0  0  0  0
 24 21  1  0  0  0  0
 25 22  2  0  0  0  0
 26 22  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0304284

> <DATABASE_NAME>
hmdb

> <SMILES>
CCCCCC1=CC(O)=C(CC=C(C)CCC=C(C)C)C(O)=C1C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C22H32O4/c1-5-6-7-11-17-14-19(23)18(21(24)20(17)22(25)26)13-12-16(4)10-8-9-15(2)3/h9,12,14,23-24H,5-8,10-11,13H2,1-4H3,(H,25,26)

> <INCHI_KEY>
SEEZIOZEUUMJME-UHFFFAOYSA-N

> <FORMULA>
C22H32O4

> <MOLECULAR_WEIGHT>
360.494

> <EXACT_MASS>
360.23005951

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
58

> <JCHEM_AVERAGE_POLARIZABILITY>
42.633936693448575

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-(3,7-dimethylocta-2,6-dien-1-yl)-2,4-dihydroxy-6-pentylbenzoic acid

> <ALOGPS_LOGP>
5.31

> <JCHEM_LOGP>
7.353675404333334

> <ALOGPS_LOGS>
-4.48

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
9.700709372280667

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.9163853279065366

> <JCHEM_PKA_STRONGEST_BASIC>
-5.8183565341602845

> <JCHEM_POLAR_SURFACE_AREA>
77.76

> <JCHEM_REFRACTIVITY>
108.76659999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.20e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-(3,7-dimethylocta-2,6-dien-1-yl)-2,4-dihydroxy-6-pentylbenzoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0304284
     RDKit          3D
cannabigerolate
 58 58  0  0  0  0  0  0  0  0999 V2000
   -6.2999    1.5853   -0.9482 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9266    0.2388   -0.9076 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1650   -0.9367   -0.5014 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5833   -1.1047    0.8319 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4891   -0.2698    1.3479 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1875   -0.3692    0.6612 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8570    0.5690   -0.2956 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6927    0.4987   -1.0152 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4028    1.4778   -1.9811 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8257   -0.5258   -0.7862 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4765   -0.6257   -1.5474 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4342    0.3314   -0.9483 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5966   -0.0499   -0.4362 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0220   -1.4699   -0.4280 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4896    0.9773    0.1525 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8014    1.0040   -0.5725 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6764    2.0497    0.0497 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8361    1.6810    0.5671 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7451    2.6723    1.1975 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2786    0.2471    0.5359 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1128   -1.5107    0.1817 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1816   -2.4692    0.3139 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2961   -1.4142    0.8960 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5220   -2.3915    1.9244 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5389   -2.4143    2.6374 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6026   -3.3879    2.1912 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0344    2.0614   -0.0186 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4525    1.5578   -1.6810 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0387    2.3396   -1.4240 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2677    0.0477   -1.9931 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9541    0.2896   -0.3989 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3716   -1.0995   -1.3266 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7992   -1.8841   -0.6811 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2963   -2.2019    0.9170 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4643   -1.0784    1.5782 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7583    0.8349    1.3639 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3345   -0.4707    2.4298 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5156    1.3776   -0.4612 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5580    1.3994   -2.4974 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8264   -1.6740   -1.4233 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2942   -0.3670   -2.5892 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1759    1.3796   -0.9241 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8312   -1.9866   -1.3782 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5208   -2.0368    0.4067 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1101   -1.5617   -0.2148 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5967    0.7223    1.2309 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0104    1.9906    0.1198 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6210    1.3003   -1.6150 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3016    0.0215   -0.5991 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3918    3.0763    0.0871 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2845    2.9901    2.1732 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7527    2.2722    1.3597 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8177    3.5865    0.5706 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2812    0.1317    0.9856 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5040   -0.3396    1.0514 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3311   -0.0908   -0.5271 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0705   -3.2430    0.8428 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4084   -3.7376    3.1204 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
 12 13  2  3
 13 14  1  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  2  3
 18 19  1  0
 18 20  1  0
 10 21  1  0
 21 22  1  0
 21 23  2  0
 23 24  1  0
 24 25  2  0
 24 26  1  0
 23  6  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
  2 30  1  0
  2 31  1  0
  3 32  1  0
  3 33  1  0
  4 34  1  0
  4 35  1  0
  5 36  1  0
  5 37  1  0
  7 38  1  0
  9 39  1  0
 11 40  1  0
 11 41  1  0
 12 42  1  0
 14 43  1  0
 14 44  1  0
 14 45  1  0
 15 46  1  0
 15 47  1  0
 16 48  1  0
 16 49  1  0
 17 50  1  0
 19 51  1  0
 19 52  1  0
 19 53  1  0
 20 54  1  0
 20 55  1  0
 20 56  1  0
 22 57  1  0
 26 58  1  0
M  END

HEADER    PROTEIN                                 31-JUL-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   31-JUL-20         0                                  
HETATM    1  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      20.005  -6.930   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      18.672  -9.240   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      13.337  -9.240   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      16.004  -7.700   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      17.338  -6.930   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      14.671  -6.930   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      12.003  -6.930   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      10.669  -7.700   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.002  -4.620   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      18.672  -7.700   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      13.337  -7.700   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.668  -5.390   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       9.336  -6.930   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       9.336  -5.390   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.668  -6.930   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       8.002  -7.700   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       5.335  -7.700   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      10.669  -4.620   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       8.002  -9.240   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0       5.335  -9.240   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0       4.001  -6.930   0.000  0.00  0.00           O+0
CONECT    1    5                                                            
CONECT    2   15                                                            
CONECT    3   15                                                            
CONECT    4   16                                                            
CONECT    5    1    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6   11                                                       
CONECT    8    9   10                                                       
CONECT    9    8   15                                                       
CONECT   10    8   16                                                       
CONECT   11    7   17                                                       
CONECT   12   13   16                                                       
CONECT   13   12   18                                                       
CONECT   14   17   19                                                       
CONECT   15    2    3    9                                                  
CONECT   16    4   10   12                                                  
CONECT   17   11   14   20                                                  
CONECT   18   13   19   21                                                  
CONECT   19   14   18   23                                                  
CONECT   20   17   21   22                                                  
CONECT   21   18   20   24                                                  
CONECT   22   20   25   26                                                  
CONECT   23   19                                                            
CONECT   24   21                                                            
CONECT   25   22                                                            
CONECT   26   22                                                            
MASTER        0    0    0    0    0    0    0    0   26    0   52    0
END

COMPND    HMDB0304284
HETATM    1  C1  UNL     1      -6.300   1.585  -0.948  1.00  0.00           C  
HETATM    2  C2  UNL     1      -6.927   0.239  -0.908  1.00  0.00           C  
HETATM    3  C3  UNL     1      -6.165  -0.937  -0.501  1.00  0.00           C  
HETATM    4  C4  UNL     1      -5.583  -1.105   0.832  1.00  0.00           C  
HETATM    5  C5  UNL     1      -4.489  -0.270   1.348  1.00  0.00           C  
HETATM    6  C6  UNL     1      -3.187  -0.369   0.661  1.00  0.00           C  
HETATM    7  C7  UNL     1      -2.857   0.569  -0.296  1.00  0.00           C  
HETATM    8  C8  UNL     1      -1.693   0.499  -1.015  1.00  0.00           C  
HETATM    9  O1  UNL     1      -1.403   1.478  -1.981  1.00  0.00           O  
HETATM   10  C9  UNL     1      -0.826  -0.526  -0.786  1.00  0.00           C  
HETATM   11  C10 UNL     1       0.476  -0.626  -1.547  1.00  0.00           C  
HETATM   12  C11 UNL     1       1.434   0.331  -0.948  1.00  0.00           C  
HETATM   13  C12 UNL     1       2.597  -0.050  -0.436  1.00  0.00           C  
HETATM   14  C13 UNL     1       3.022  -1.470  -0.428  1.00  0.00           C  
HETATM   15  C14 UNL     1       3.490   0.977   0.153  1.00  0.00           C  
HETATM   16  C15 UNL     1       4.801   1.004  -0.573  1.00  0.00           C  
HETATM   17  C16 UNL     1       5.676   2.050   0.050  1.00  0.00           C  
HETATM   18  C17 UNL     1       6.836   1.681   0.567  1.00  0.00           C  
HETATM   19  C18 UNL     1       7.745   2.672   1.198  1.00  0.00           C  
HETATM   20  C19 UNL     1       7.279   0.247   0.536  1.00  0.00           C  
HETATM   21  C20 UNL     1      -1.113  -1.511   0.182  1.00  0.00           C  
HETATM   22  O2  UNL     1      -0.182  -2.469   0.314  1.00  0.00           O  
HETATM   23  C21 UNL     1      -2.296  -1.414   0.896  1.00  0.00           C  
HETATM   24  C22 UNL     1      -2.522  -2.392   1.924  1.00  0.00           C  
HETATM   25  O3  UNL     1      -3.539  -2.414   2.637  1.00  0.00           O  
HETATM   26  O4  UNL     1      -1.603  -3.388   2.191  1.00  0.00           O  
HETATM   27  H1  UNL     1      -6.034   2.061  -0.019  1.00  0.00           H  
HETATM   28  H2  UNL     1      -5.453   1.558  -1.681  1.00  0.00           H  
HETATM   29  H3  UNL     1      -7.039   2.340  -1.424  1.00  0.00           H  
HETATM   30  H4  UNL     1      -7.268   0.048  -1.993  1.00  0.00           H  
HETATM   31  H5  UNL     1      -7.954   0.290  -0.399  1.00  0.00           H  
HETATM   32  H6  UNL     1      -5.372  -1.100  -1.327  1.00  0.00           H  
HETATM   33  H7  UNL     1      -6.799  -1.884  -0.681  1.00  0.00           H  
HETATM   34  H8  UNL     1      -5.296  -2.202   0.917  1.00  0.00           H  
HETATM   35  H9  UNL     1      -6.464  -1.078   1.578  1.00  0.00           H  
HETATM   36  H10 UNL     1      -4.758   0.835   1.364  1.00  0.00           H  
HETATM   37  H11 UNL     1      -4.335  -0.471   2.430  1.00  0.00           H  
HETATM   38  H12 UNL     1      -3.516   1.378  -0.461  1.00  0.00           H  
HETATM   39  H13 UNL     1      -0.558   1.399  -2.497  1.00  0.00           H  
HETATM   40  H14 UNL     1       0.826  -1.674  -1.423  1.00  0.00           H  
HETATM   41  H15 UNL     1       0.294  -0.367  -2.589  1.00  0.00           H  
HETATM   42  H16 UNL     1       1.176   1.380  -0.924  1.00  0.00           H  
HETATM   43  H17 UNL     1       2.831  -1.987  -1.378  1.00  0.00           H  
HETATM   44  H18 UNL     1       2.521  -2.037   0.407  1.00  0.00           H  
HETATM   45  H19 UNL     1       4.110  -1.562  -0.215  1.00  0.00           H  
HETATM   46  H20 UNL     1       3.597   0.722   1.231  1.00  0.00           H  
HETATM   47  H21 UNL     1       3.010   1.991   0.120  1.00  0.00           H  
HETATM   48  H22 UNL     1       4.621   1.300  -1.615  1.00  0.00           H  
HETATM   49  H23 UNL     1       5.302   0.021  -0.599  1.00  0.00           H  
HETATM   50  H24 UNL     1       5.392   3.076   0.087  1.00  0.00           H  
HETATM   51  H25 UNL     1       7.285   2.990   2.173  1.00  0.00           H  
HETATM   52  H26 UNL     1       8.753   2.272   1.360  1.00  0.00           H  
HETATM   53  H27 UNL     1       7.818   3.587   0.571  1.00  0.00           H  
HETATM   54  H28 UNL     1       8.281   0.132   0.986  1.00  0.00           H  
HETATM   55  H29 UNL     1       6.504  -0.340   1.051  1.00  0.00           H  
HETATM   56  H30 UNL     1       7.331  -0.091  -0.527  1.00  0.00           H  
HETATM   57  H31 UNL     1      -0.071  -3.243   0.843  1.00  0.00           H  
HETATM   58  H32 UNL     1      -1.408  -3.738   3.120  1.00  0.00           H  
CONECT    1    2   27   28   29
CONECT    2    3   30   31
CONECT    3    4   32   33
CONECT    4    5   34   35
CONECT    5    6   36   37
CONECT    6    7    7   23
CONECT    7    8   38
CONECT    8    9   10   10
CONECT    9   39
CONECT   10   11   21
CONECT   11   12   40   41
CONECT   12   13   13   42
CONECT   13   14   15
CONECT   14   43   44   45
CONECT   15   16   46   47
CONECT   16   17   48   49
CONECT   17   18   18   50
CONECT   18   19   20
CONECT   19   51   52   53
CONECT   20   54   55   56
CONECT   21   22   23   23
CONECT   22   57
CONECT   23   24
CONECT   24   25   25   26
CONECT   26   58
END

HMDB0304284
     RDKit          3D
cannabigerolate
 58 58  0  0  0  0  0  0  0  0999 V2000
   -6.2999    1.5853   -0.9482 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9266    0.2388   -0.9076 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1650   -0.9367   -0.5014 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5833   -1.1047    0.8319 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4891   -0.2698    1.3479 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1875   -0.3692    0.6612 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8570    0.5690   -0.2956 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6927    0.4987   -1.0152 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4028    1.4778   -1.9811 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8257   -0.5258   -0.7862 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4765   -0.6257   -1.5474 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4342    0.3314   -0.9483 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5966   -0.0499   -0.4362 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0220   -1.4699   -0.4280 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4896    0.9773    0.1525 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8014    1.0040   -0.5725 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6764    2.0497    0.0497 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8361    1.6810    0.5671 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7451    2.6723    1.1975 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2786    0.2471    0.5359 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1128   -1.5107    0.1817 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1816   -2.4692    0.3139 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2961   -1.4142    0.8960 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5220   -2.3915    1.9244 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5389   -2.4143    2.6374 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6026   -3.3879    2.1912 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0344    2.0614   -0.0186 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4525    1.5578   -1.6810 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0387    2.3396   -1.4240 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2677    0.0477   -1.9931 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9541    0.2896   -0.3989 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3716   -1.0995   -1.3266 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7992   -1.8841   -0.6811 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2963   -2.2019    0.9170 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4643   -1.0784    1.5782 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7583    0.8349    1.3639 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3345   -0.4707    2.4298 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5156    1.3776   -0.4612 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5580    1.3994   -2.4974 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8264   -1.6740   -1.4233 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2942   -0.3670   -2.5892 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1759    1.3796   -0.9241 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8312   -1.9866   -1.3782 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5208   -2.0368    0.4067 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1101   -1.5617   -0.2148 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5967    0.7223    1.2309 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0104    1.9906    0.1198 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6210    1.3003   -1.6150 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3016    0.0215   -0.5991 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3918    3.0763    0.0871 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2845    2.9901    2.1732 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7527    2.2722    1.3597 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8177    3.5865    0.5706 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2812    0.1317    0.9856 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5040   -0.3396    1.0514 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3311   -0.0908   -0.5271 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0705   -3.2430    0.8428 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4084   -3.7376    3.1204 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
 12 13  2  3
 13 14  1  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  2  3
 18 19  1  0
 18 20  1  0
 10 21  1  0
 21 22  1  0
 21 23  2  0
 23 24  1  0
 24 25  2  0
 24 26  1  0
 23  6  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
  2 30  1  0
  2 31  1  0
  3 32  1  0
  3 33  1  0
  4 34  1  0
  4 35  1  0
  5 36  1  0
  5 37  1  0
  7 38  1  0
  9 39  1  0
 11 40  1  0
 11 41  1  0
 12 42  1  0
 14 43  1  0
 14 44  1  0
 14 45  1  0
 15 46  1  0
 15 47  1  0
 16 48  1  0
 16 49  1  0
 17 50  1  0
 19 51  1  0
 19 52  1  0
 19 53  1  0
 20 54  1  0
 20 55  1  0
 20 56  1  0
 22 57  1  0
 26 58  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
3-(3,7-Dimethylocta-2,6-dien-1-yl)-2,4-dihydroxy-6-pentylbenzoate	Generator
Cannabigerolic acid	Generator

Chemical Formula

C₂₂H₃₂O₄

Average Molecular Weight

360.494

Monoisotopic Molecular Weight

360.23005951

IUPAC Name

3-(3,7-dimethylocta-2,6-dien-1-yl)-2,4-dihydroxy-6-pentylbenzoic acid

Traditional Name

3-(3,7-dimethylocta-2,6-dien-1-yl)-2,4-dihydroxy-6-pentylbenzoic acid

CAS Registry Number

Not Available

SMILES

CCCCCC1=CC(O)=C(CC=C(C)CCC=C(C)C)C(O)=C1C(O)=O

InChI Identifier

InChI=1S/C22H32O4/c1-5-6-7-11-17-14-19(23)18(21(24)20(17)22(25)26)13-12-16(4)10-8-9-15(2)3/h9,12,14,23-24H,5-8,10-11,13H2,1-4H3,(H,25,26)

InChI Key

SEEZIOZEUUMJME-UHFFFAOYSA-N

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
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

Not Available

Ontology

Not Available

Exogenous (HMDB: HMDB0304284)

Herbs and Spices (FooDB: FOOD00866)

Nut

Almond (FooDB: FOOD00148)
Brazil nut (FooDB: FOOD00024)
Cashew nut (FooDB: FOOD00011)
Chestnut (FooDB: FOOD00045)
Hazelnut (FooDB: FOOD00376)
Peanut (FooDB: FOOD00016)
Pecan nut (FooDB: FOOD00044)
Pine nut (FooDB: FOOD00138)
Pistachio (FooDB: FOOD00140)
Walnut (FooDB: FOOD00608)
Acorn (FooDB: FOOD00282)
Beech nut (FooDB: FOOD00299)
Butternut (FooDB: FOOD00316)
Chinese chestnut (FooDB: FOOD00331)
European chestnut (FooDB: FOOD00363)
Hickory nut (FooDB: FOOD00377)
Macadamia nut (FooDB: FOOD00525)
Mixed nuts (FooDB: FOOD00771)
Pili nut (FooDB: FOOD00432)
Colorado pinyon (FooDB: FOOD00433)
Black walnut (FooDB: FOOD00093)
Common walnut (FooDB: FOOD00094)
Japanese chestnut (FooDB: FOOD00385)
Common hazelnut (FooDB: FOOD00062)
Macadamia nut (M. tetraphylla) (FooDB: FOOD00225)
Japanese walnut (FooDB: FOOD00240)
Nuts (FooDB: FOOD00869)

Fruit

Pome

Drupe

Apricot (FooDB: FOOD00144)
Prunus (Cherry, Plum) (FooDB: FOOD00143)
Nectarine (FooDB: FOOD00229)
Peach (FooDB: FOOD00149)
European plum (FooDB: FOOD00147)
Sour cherry (FooDB: FOOD00146)
Sweet cherry (FooDB: FOOD00145)
Common chokecherry (FooDB: FOOD00562)
Peach (var.) (FooDB: FOOD00230)

Tropical fruit

Berry

Bilberry (FooDB: FOOD00193)
Rubus (Blackberry, Raspberry) (FooDB: FOOD00160)
Vaccinium (Blueberry, Cranberry, Huckleberry) (FooDB: FOOD00188)
Blackcurrant (FooDB: FOOD00155)
Redcurrant (FooDB: FOOD00156)
Elderberry (FooDB: FOOD00358)
Gooseberry (FooDB: FOOD00157)
Grape (FooDB: FOOD00369)
Lingonberry (FooDB: FOOD00194)
Loganberry (FooDB: FOOD00400)
Strawberry (FooDB: FOOD00083)
Boysenberry (FooDB: FOOD00542)
American cranberry (FooDB: FOOD00192)
Common grape (FooDB: FOOD00204)
Strawberry guava (FooDB: FOOD00482)
Black mulberry (FooDB: FOOD00117)
Red raspberry (FooDB: FOOD00162)
Muscadine grape (FooDB: FOOD00203)
Salmonberry (FooDB: FOOD00456)
Alaska blueberry (FooDB: FOOD00380)
Sea-buckthornberry (FooDB: FOOD00087)
Black elderberry (FooDB: FOOD00166)
Black crowberry (FooDB: FOOD00075)
Black huckleberry (FooDB: FOOD00084)
Mulberry (FooDB: FOOD00116)
Black chokeberry (FooDB: FOOD00136)
Cloudberry (FooDB: FOOD00161)
Black raspberry (FooDB: FOOD00163)
Rowanberry (FooDB: FOOD00176)
Lowbush blueberry (FooDB: FOOD00189)
Sparkleberry (FooDB: FOOD00190)
Highbush blueberry (FooDB: FOOD00191)
Arctic blackberry (FooDB: FOOD00207)
Bayberry (FooDB: FOOD00209)
Elliott's blueberry (FooDB: FOOD00210)
Canada blueberry (FooDB: FOOD00211)
Bog bilberry (FooDB: FOOD00212)
Buffalo currant (FooDB: FOOD00213)
European cranberry (FooDB: FOOD00217)
Deerberry (FooDB: FOOD00218)
Cascade huckleberry (FooDB: FOOD00220)
Oval-leaf huckleberry (FooDB: FOOD00221)
Evergreen huckleberry (FooDB: FOOD00222)
Red huckleberry (FooDB: FOOD00223)
Summer grape (FooDB: FOOD00227)
Fox grape (FooDB: FOOD00228)
Half-highbush blueberry (FooDB: FOOD00248)
Jostaberry (FooDB: FOOD00257)
Sweet rowanberry (FooDB: FOOD00265)
Skunk currant (FooDB: FOOD00267)
Squashberry (FooDB: FOOD00344)
Ohelo berry (FooDB: FOOD00419)
Chinese bayberry (FooDB: FOOD00852)
Saskatoon berry (FooDB: FOOD00884)
Nanking cherry (FooDB: FOOD00885)

Other fruit

Date (FooDB: FOOD00135)
Fig (FooDB: FOOD00081)
Jujube (FooDB: FOOD00388)

Citrus

Grapefruit (FooDB: FOOD00256)
Lemon (FooDB: FOOD00054)
Lime (FooDB: FOOD00053)
Sweet orange (FooDB: FOOD00057)
Mandarin orange (Clementine, Tangerine) (FooDB: FOOD00056)
Persian lime (FooDB: FOOD00543)
Pummelo (FooDB: FOOD00055)
Grapefruit/Pummelo hybrid (FooDB: FOOD00255)
Citrus (FooDB: FOOD00859)

Fruits (FooDB: FOOD00871)

Vegetable

Shoot vegetable

Fruit vegetable

Eggplant (FooDB: FOOD00174)
Avocado (FooDB: FOOD00130)
Groundcherry (FooDB: FOOD00371)
Olive (FooDB: FOOD00121)
Pepper (FooDB: FOOD00040)
Garden tomato (FooDB: FOOD00171)
Mexican groundcherry (FooDB: FOOD00491)
Green bell pepper (FooDB: FOOD00877)
Yellow bell pepper (FooDB: FOOD00878)
Red bell pepper (FooDB: FOOD00880)
Italian sweet red pepper (FooDB: FOOD00881)
Garden tomato (var.) (FooDB: FOOD00173)
Cherry tomato (FooDB: FOOD00172)
Pepper (C. baccatum) (FooDB: FOOD00231)
Pepper (C. chinense) (FooDB: FOOD00232)
Pepper (Capsicum) (FooDB: FOOD00233)
Pepper (C. frutescens) (FooDB: FOOD00428)
Pepper (C. pubescens) (FooDB: FOOD00849)
Orange bell pepper (FooDB: FOOD00879)

Root vegetable

Cabbage

Leaf vegetable

Lettuce (FooDB: FOOD00095)
Swiss chard (FooDB: FOOD00237)
Garden cress (FooDB: FOOD00099)
Endive (FooDB: FOOD00048)
Spinach (FooDB: FOOD00178)
Common beet (FooDB: FOOD00025)
Garland chrysanthemum (FooDB: FOOD00333)
Jute (FooDB: FOOD00389)
Lambsquarters (FooDB: FOOD00394)
New Zealand spinach (FooDB: FOOD00415)
Swamp cabbage (FooDB: FOOD00091)
Rocket salad (ssp.) (FooDB: FOOD00077)
Yautia (FooDB: FOOD00510)
Romaine lettuce (FooDB: FOOD00888)
Rocket salad (FooDB: FOOD00244)
Chicory leaves (FooDB: FOOD00250)
Corn salad (FooDB: FOOD00340)
Malabar spinach (FooDB: FOOD00404)
Ostrich fern (FooDB: FOOD00556)
Green vegetables (FooDB: FOOD00872)

Mushroom

Tuber

Onion-family vegetable

Leek (FooDB: FOOD00007)
Allium (FooDB: FOOD00005)
Wild leek (FooDB: FOOD00396)
Shallot (FooDB: FOOD00243)
Garden onion (FooDB: FOOD00006)
Garden onion (var.) (FooDB: FOOD00226)
Onion-family vegetables (FooDB: FOOD00855)
Green onion (FooDB: FOOD00963)
Red onion (FooDB: FOOD00962)

Other vegetable

Okra (FooDB: FOOD00420)
Horseradish tree (FooDB: FOOD00379)
Sacred lotus (FooDB: FOOD00402)
Tree fern (FooDB: FOOD00797)
Chinese water chestnut (FooDB: FOOD00332)
Nopal (FooDB: FOOD00416)
Carob (FooDB: FOOD00321)
Agave (FooDB: FOOD00563)
Narrowleaf cattail (FooDB: FOOD00564)
Giant butterbur (FooDB: FOOD00314)
Sesbania flower (FooDB: FOOD00469)

Stalk vegetable

Brassica

Brassicas (FooDB: FOOD00857)

Cereal and cereal product

Other bread

Other bread (FooDB: FOOD00269)

Cereal

Cereal product

Dough

Sourdough (FooDB: FOOD00275)

Cereals and cereal products (FooDB: FOOD00858)

Pulse

Bean

Lentil

Lentils (FooDB: FOOD00098)

Pea

Other pulse

White lupine (FooDB: FOOD00403)
Lupine (FooDB: FOOD00104)

Pulses (FooDB: FOOD00867)

Soy

Soy bean (FooDB: FOOD00085)

Soy product

Other soy product (FooDB: FOOD00271)

Abalone (FooDB: FOOD00279)
Conch (FooDB: FOOD00611)

Gourd

Chayote (FooDB: FOOD00325)
Cucumber (FooDB: FOOD00065)
Muskmelon (FooDB: FOOD00064)
Cucurbita (FooDB: FOOD00066)
Watermelon (FooDB: FOOD00052)
Bitter gourd (FooDB: FOOD00115)
Calabash (FooDB: FOOD00318)
Towel gourd (FooDB: FOOD00492)
Winter squash (FooDB: FOOD00283)
Butternut squash (FooDB: FOOD00317)
Wax gourd (FooDB: FOOD00499)
Green zucchini (FooDB: FOOD00875)
Yellow zucchini (FooDB: FOOD00876)
Japanese pumpkin (FooDB: FOOD00886)
Sunburst squash (pattypan squash) (FooDB: FOOD00874)
Tinda (FooDB: FOOD00559)
Horned melon (FooDB: FOOD00761)

Tea

Herbal tea

Greenthread tea (FooDB: FOOD00820)

Cocoa and cocoa product

Cocoa

Cocoa bean (FooDB: FOOD00182)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular 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

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	5.31	ALOGPS
logP	7.35	ChemAxon
logS	-4.5	ALOGPS
pKa (Strongest Acidic)	2.92	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	10	ChemAxon
Refractivity	108.77 m³·mol⁻¹	ChemAxon
Polarizability	42.63 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
AllCCS	[M+H]+	194.681	32859911
AllCCS	[M+H-H2O]+	191.917	32859911
AllCCS	[M+Na]+	197.967	32859911
AllCCS	[M+NH4]+	197.235	32859911
AllCCS	[M-H]-	194.284	32859911
AllCCS	[M+Na-2H]-	195.606	32859911
AllCCS	[M+HCOO]-	197.218	32859911
DeepCCS	[M+H]+	199.494	30932474
DeepCCS	[M-H]-	197.06	30932474
DeepCCS	[M-2H]-	230.996	30932474
DeepCCS	[M+Na]+	207.003	30932474

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Predicted by Siyang on May 30, 2022	21.0646 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.04 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	3384.1 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	520.6 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	243.3 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	254.8 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	286.6 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	979.4 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	991.0 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	84.3 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1869.5 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	793.4 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1717.5 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	633.9 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	545.9 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	269.2 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	384.6 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	8.4 seconds	40023050

Predicted Kovats Retention Indices

Not Available

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - cannabigerolate GC-MS (1 TMS) - 70eV, Positive	Not Available	2020-06-30	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - cannabigerolate GC-MS (1 TMS) - 70eV, Positive	Not Available	2020-06-30	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - cannabigerolate GC-MS (1 TMS) - 70eV, Positive	Not Available	2020-06-30	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - cannabigerolate GC-MS (2 TMS) - 70eV, Positive	Not Available	2020-06-30	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - cannabigerolate GC-MS (2 TMS) - 70eV, Positive	Not Available	2020-06-30	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - cannabigerolate GC-MS (2 TMS) - 70eV, Positive	Not Available	2020-06-30	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - cannabigerolate GC-MS (3 TMS) - 70eV, Positive	Not Available	2020-06-30	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - cannabigerolate 10V, Positive-QTOF	splash10-03xu-0119000000-b8e5c06544056dd55091	2015-05-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - cannabigerolate 20V, Positive-QTOF	splash10-05to-6957000000-cb8ac2f7deabc706cd56	2015-05-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - cannabigerolate 40V, Positive-QTOF	splash10-0ldl-9330000000-c7e7b332c6c5845bc49b	2015-05-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - cannabigerolate 10V, Negative-QTOF	splash10-0aor-0009000000-f612500589c166d6bd84	2015-05-27	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - cannabigerolate 20V, Negative-QTOF	splash10-014i-0119000000-9843f3bdf4bed8e477cf	2015-05-27	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - cannabigerolate 40V, Negative-QTOF	splash10-002b-1974000000-f64241ac053166d0e6da	2015-05-27	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - cannabigerolate 10V, Positive-QTOF	splash10-03di-2029000000-15e29defeb1cc4528edc	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - cannabigerolate 20V, Positive-QTOF	splash10-001r-9183000000-626fa32d60f248181dfd	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - cannabigerolate 40V, Positive-QTOF	splash10-0006-9210000000-ca31895d0fab30e1ae60	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - cannabigerolate 10V, Negative-QTOF	splash10-0a4l-0009000000-1d04fad9fcf034954bb1	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - cannabigerolate 20V, Negative-QTOF	splash10-0a4i-0119000000-a0af8bbe8d2db5c09ac5	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - cannabigerolate 40V, Negative-QTOF	splash10-0a71-1491000000-78b3b6f8d3f55214d92d	2021-10-21	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB030712

KNApSAcK ID

Not Available

Chemspider ID

26459938

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

3082240

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. [PubMed:6991645 ]
Zirpel B, Degenhardt F, Martin C, Kayser O, Stehle F: Engineering yeasts as platform organisms for cannabinoid biosynthesis. J Biotechnol. 2017 Oct 10;259:204-212. doi: 10.1016/j.jbiotec.2017.07.008. Epub 2017 Jul 8. [PubMed:28694184 ]

Showing metabocard for cannabigerolate (HMDB0304284)

MOL for HMDB0304284 (cannabigerolate)

3D MOL for HMDB0304284 (cannabigerolate)

3D SDF for HMDB0304284 (cannabigerolate)

3D-SDF for HMDB0304284 (cannabigerolate)

PDB for HMDB0304284 (cannabigerolate)

3D PDB for HMDB0304284 (cannabigerolate)

SMILES for HMDB0304284 (cannabigerolate)

INCHI for HMDB0304284 (cannabigerolate)

Structure for HMDB0304284 (cannabigerolate)

3D Structure for HMDB0304284 (cannabigerolate)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

GC-MS Spectra

MS/MS Spectra