NP-MRD: Showing NP-Card for Cannabigerolic acid monomethylether (NP0044837)

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Record Information

Version

2.0

Created at

2022-03-10 18:36:21 UTC

Updated at

2022-03-10 22:19:10 UTC

NP-MRD ID

NP0044837

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Cannabigerolic acid monomethylether

Description

Cannabigerolic acid monomethyl ether or CBGAM is the methylated derivative of cannabigerolic acid in position four of the aromatic ring. As such, it is a phytocannabinoid that belongs to the class of organic compounds known as hydroxybenzoic acid derivatives. As a derivative of cannabigerolic acid, it is derived from olivetolic acid on which the hydrogen at position 3 is substituted by a geranyl group. CBGAM 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, cannabigerolic acid monomethylether can be considered a polyketide and a monoterpenoid. In a study of the biosynthetic pathway of cannabinoid acids using four strains of Cannibus sativa L. (Mexican, Minamioshihara-1 and Domestic-l and 2; D-l and D2), 3 of the 4 strains produced THC as the major constituent but not the Domestic 2 strain, which only produced cannabigerolic acid. The Mexican strain also produced CBGAM as second major constituent ( https://Www.Thevespiary.Org/rhodium/Rhodium/Vespiary/talk/files/4661-Biosynthesis-of-cannabinoid-acids-6d99.Pdf). This suggested that all cannabis plants do not produce THC and some may accumulate other intermediates in the pathway to THC such as CBGAM. ¬†

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652307312018162D          

 28 28  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
    6.4302   -2.8875    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
    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
    5.7158   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -3.3000    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  6  1  1  0  0  0  0
  7  6  1  0  0  0  0
  8  7  1  0  0  0  0
 10  9  1  0  0  0  0
 11  9  1  0  0  0  0
 12  8  1  0  0  0  0
 14 13  1  0  0  0  0
 16  2  1  0  0  0  0
 16  3  1  0  0  0  0
 16 10  2  0  0  0  0
 17  4  1  0  0  0  0
 17 11  1  0  0  0  0
 17 13  2  0  0  0  0
 18 12  1  0  0  0  0
 18 15  2  0  0  0  0
 19 14  1  0  0  0  0
 20 15  1  0  0  0  0
 20 19  2  0  0  0  0
 21 18  1  0  0  0  0
 22 19  1  0  0  0  0
 22 21  2  0  0  0  0
 23 21  1  0  0  0  0
 24 22  1  0  0  0  0
 25 23  2  0  0  0  0
 26 23  1  0  0  0  0
 27  5  1  0  0  0  0
 27 20  1  0  0  0  0
 28 13  1  0  0  0  0
M  END

     RDKit          3D

 61 61  0  0  0  0  0  0  0  0999 V2000
   -8.7345    0.2343   -0.9320 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3501   -0.1977   -0.4385 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6049    0.9648    0.1457 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2371    0.6331    0.6807 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3834    0.1013   -0.4195 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0289   -0.2668   -0.0242 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9904    0.6190   -0.2426 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6834    0.3398    0.1461 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3236    1.2589   -0.0954 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0058    2.4756   -0.7366 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3995   -0.8364    0.7619 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9804   -1.2248    1.2221 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9704   -0.1614    1.0340 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0124   -0.3512    0.2548 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2044   -1.6471   -0.4479 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0347    0.7040    0.0352 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4074    0.2195    0.4909 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3719    1.3131    0.2347 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3962    1.0903   -0.5747 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5519   -0.2311   -1.1971 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4012    2.1704   -0.8665 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4268   -1.7325    0.9866 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1909   -2.9462    1.6107 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7424   -1.4563    0.5967 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7556   -2.4730    0.8525 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9682   -2.3731    0.5614 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3524   -3.6717    1.4775 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2987   -0.6818   -1.2353 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6884    0.9002   -1.7923 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.3176    0.6907   -0.1104 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4916   -0.9783    0.3345 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8410   -0.6834   -1.2880 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4869    1.7009   -0.7058 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2189    1.5013    0.8995 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8095    1.6216    1.0479 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3333    0.0252    1.5805 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9056   -0.7197   -0.9338 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3141    0.9709   -1.1655 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2178    1.5508   -0.7305 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8151    2.9342   -0.1188 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8406    3.1885   -0.7394 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3794    2.2850   -1.7795 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9438   -1.5775    2.2781 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2673   -2.1163    0.6306 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8775    0.7972    1.5320 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1209   -1.6519   -1.0750 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2447   -2.4681    0.3234 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3264   -1.8687   -1.0872 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0619    1.0145   -1.0185 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8009    1.6077    0.6458 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3752    0.0411    1.6061 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6744   -0.7079   -0.0422 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2643    2.2756    0.6842 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4734   -0.2512   -1.8133 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6560   -0.9854   -0.3817 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6771   -0.5439   -1.8077 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3470    2.9532   -0.0867 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1721    2.5709   -1.8602 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.4031    1.6784   -0.9174 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2878   -3.2458    1.9307 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9325   -4.3824    0.8652 H   0  0  0  0  0  0  0  0  0  0  0  0
 13 12  1  0
 12 11  1  0
 11  8  2  0
  8  9  1  0
  9 10  1  0
  8  7  1  0
  7  6  2  0
  6  5  1  0
  5  4  1  0
  4  3  1  0
  3  2  1  0
  2  1  1  0
  6 24  1  0
 24 25  1  0
 25 27  1  0
 25 26  2  0
 24 22  2  0
 22 23  1  0
 13 14  2  0
 14 15  1  0
 14 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  3
 19 20  1  0
 19 21  1  0
 22 11  1  0
 13 45  1  0
 12 43  1  0
 12 44  1  0
 10 40  1  0
 10 41  1  0
 10 42  1  0
  7 39  1  0
  5 37  1  0
  5 38  1  0
  4 35  1  0
  4 36  1  0
  3 33  1  0
  3 34  1  0
  2 31  1  0
  2 32  1  0
  1 28  1  0
  1 29  1  0
  1 30  1  0
 27 61  1  0
 23 60  1  0
 15 46  1  0
 15 47  1  0
 15 48  1  0
 16 49  1  0
 16 50  1  0
 17 51  1  0
 17 52  1  0
 18 53  1  0
 20 54  1  0
 20 55  1  0
 20 56  1  0
 21 57  1  0
 21 58  1  0
 21 59  1  0
M  END


  Mrv1652307312018162D          

 28 28  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
    6.4302   -2.8875    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
    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
    5.7158   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -3.3000    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  6  1  1  0  0  0  0
  7  6  1  0  0  0  0
  8  7  1  0  0  0  0
 10  9  1  0  0  0  0
 11  9  1  0  0  0  0
 12  8  1  0  0  0  0
 14 13  1  0  0  0  0
 16  2  1  0  0  0  0
 16  3  1  0  0  0  0
 16 10  2  0  0  0  0
 17  4  1  0  0  0  0
 17 11  1  0  0  0  0
 17 13  2  0  0  0  0
 18 12  1  0  0  0  0
 18 15  2  0  0  0  0
 19 14  1  0  0  0  0
 20 15  1  0  0  0  0
 20 19  2  0  0  0  0
 21 18  1  0  0  0  0
 22 19  1  0  0  0  0
 22 21  2  0  0  0  0
 23 21  1  0  0  0  0
 24 22  1  0  0  0  0
 25 23  2  0  0  0  0
 26 23  1  0  0  0  0
 27  5  1  0  0  0  0
 27 20  1  0  0  0  0
 28 13  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0044837

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]C(CC1=C(OC)C=C(CCCCC)C(C(O)=O)=C1O)=C(C)CCC=C(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C23H34O4/c1-6-7-8-12-18-15-20(27-5)19(22(24)21(18)23(25)26)14-13-17(4)11-9-10-16(2)3/h10,13,15,24H,6-9,11-12,14H2,1-5H3,(H,25,26)/b17-13+

> <INCHI_KEY>
VAFRUJRAAHLCFZ-GHRIWEEISA-N

> <FORMULA>
C23H34O4

> <MOLECULAR_WEIGHT>
374.521

> <EXACT_MASS>
374.245709575

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
61

> <JCHEM_AVERAGE_POLARIZABILITY>
44.43855836394819

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
5.56

> <JCHEM_LOGP>
7.499569460333333

> <ALOGPS_LOGS>
-5.09

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
12.301253534056887

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.902665432418568

> <JCHEM_PKA_STRONGEST_BASIC>
-4.866728236473544

> <JCHEM_POLAR_SURFACE_AREA>
66.76

> <JCHEM_REFRACTIVITY>
113.24889999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.02e-03 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

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      12.003  -5.390   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      16.004  -7.700   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      17.338  -6.930   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      14.671  -6.930   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      12.003  -6.930   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      10.669  -7.700   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.002  -4.620   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      18.672  -7.700   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      13.337  -7.700   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.668  -5.390   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       9.336  -6.930   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       9.336  -5.390   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       6.668  -6.930   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       8.002  -7.700   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       5.335  -7.700   0.000  0.00  0.00           C+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
HETATM   27  O   UNK     0      10.669  -4.620   0.000  0.00  0.00           O+0
HETATM   28  H   UNK     0      10.669  -6.160   0.000  0.00  0.00           H+0
CONECT    1    6                                                            
CONECT    2   16                                                            
CONECT    3   16                                                            
CONECT    4   17                                                            
CONECT    5   27                                                            
CONECT    6    1    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7   12                                                       
CONECT    9   10   11                                                       
CONECT   10    9   16                                                       
CONECT   11    9   17                                                       
CONECT   12    8   18                                                       
CONECT   13   14   17   28                                                  
CONECT   14   13   19                                                       
CONECT   15   18   20                                                       
CONECT   16    2    3   10                                                  
CONECT   17    4   11   13                                                  
CONECT   18   12   15   21                                                  
CONECT   19   14   20   22                                                  
CONECT   20   15   19   27                                                  
CONECT   21   18   22   23                                                  
CONECT   22   19   21   24                                                  
CONECT   23   21   25   26                                                  
CONECT   24   22                                                            
CONECT   25   23                                                            
CONECT   26   23                                                            
CONECT   27    5   20                                                       
CONECT   28   13                                                            
MASTER        0    0    0    0    0    0    0    0   28    0   56    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₃H₃₄O₄

Average Mass

374.5210 Da

Monoisotopic Mass

374.24571 Da

IUPAC Name

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

Traditional Name

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

CAS Registry Number

29624-08-6

SMILES

[H]C(CC1=C(OC)C=C(CCCCC)C(C(O)=O)=C1O)=C(C)CCC=C(C)C

InChI Identifier

InChI=1S/C23H34O4/c1-6-7-8-12-18-15-20(27-5)19(22(24)21(18)23(25)26)14-13-17(4)11-9-10-16(2)3/h10,13,15,24H,6-9,11-12,14H2,1-5H3,(H,25,26)/b17-13+

InChI Key

VAFRUJRAAHLCFZ-GHRIWEEISA-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 sativa	NULL	Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as p-methoxybenzoic acids and derivatives. These are benzoic acids in which the hydrogen atom at position 4 of the benzene ring is replaced by a methoxy group.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Benzoic acids and derivatives

Direct Parent

P-methoxybenzoic acids and derivatives

Alternative Parents

Substituents

P-methoxybenzoic acid or derivatives
Hydroxybenzoic acid
Methoxyphenol
Monocyclic monoterpenoid
Monoterpenoid
Salicylic acid or derivatives
Salicylic acid
Aromatic monoterpenoid
Benzoic acid
Benzoyl
Phenol ether
Methoxybenzene
Phenoxy compound
Anisole
Phenol
Alkyl aryl ether
1-hydroxy-4-unsubstituted benzenoid
Vinylogous acid
Ether
Carboxylic acid derivative
Carboxylic acid
Organooxygen compound
Hydrocarbon derivative
Organic oxygen compound
Organic oxide
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	5.56	ALOGPS
logP	7.5	ChemAxon
logS	-5.1	ALOGPS
pKa (Strongest Acidic)	2.9	ChemAxon
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	66.76 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	113.25 m³·mol⁻¹	ChemAxon
Polarizability	44.44 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	No	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

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

24739091

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Cannabigerolic acid monomethylether (NP0044837)

MOL for NP0044837 (Cannabigerolic acid monomethylether)

3D MOL for NP0044837 (Cannabigerolic acid monomethylether)

3D SDF for NP0044837 (Cannabigerolic acid monomethylether)

3D-SDF for NP0044837 (Cannabigerolic acid monomethylether)

PDB for NP0044837 (Cannabigerolic acid monomethylether)

3D PDB for NP0044837 (Cannabigerolic acid monomethylether)

SMILES for NP0044837 (Cannabigerolic acid monomethylether)

INCHI for NP0044837 (Cannabigerolic acid monomethylether)

Structure for NP0044837 (Cannabigerolic acid monomethylether)

3D Structure for NP0044837 (Cannabigerolic acid monomethylether)