NP-MRD: Showing NP-Card for Cannabicyclolic acid (NP0044851)

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Record Information

Version

2.0

Created at

2022-03-10 18:36:36 UTC

Updated at

2022-03-10 22:18:51 UTC

NP-MRD ID

NP0044851

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Cannabicyclolic acid

Description

Cannabicyclolic acid, also known as cannabicyclolate or CBLA, belongs to the class of organic compounds known as salicylic acid and derivatives. Salicylic acid and derivatives are compounds containing a 2-hydroxybenzoic acid moiety or a derivative thereof. Cannabicyclolic acid is a neutral compound. Cannabicyclolic acid or CBLA, has also been placed in the class of cannabis compounds known as Cannabicyclols. Cannabicyclolic acid (CBLA) is a non-psychoactive cannabinoid found in cannabis plants (PMID: 6991645 ). CBLA is a relatively rare or low-abundance compound in cannabis. It is thought to be a photo-oxidation or natural degradation product of cannabichromenic acid (CBCA). CBLA is not considered to be an original cannabinoid (PMID: 6991645 ).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652307312018222D          

 29 32  0  0  1  0            999 V2000
    7.5289   -0.9805    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4726    1.4890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6267    1.5293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8854   -1.7929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7895   -0.6146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1029   -1.0720    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3634   -0.7062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6769   -1.1636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1503   -0.2728    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1867   -1.0451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2509   -1.2552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9374   -0.7977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4687    0.3132    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5114   -0.8893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8846    0.0256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4586   -0.0660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1066   -0.1733    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7108    0.3583    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1451    0.3914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5711    0.4830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0702    0.9203    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0345   -0.9815    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0923    1.2147    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5183    1.3063    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3106    0.1171    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8031   -1.3418    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1079    0.9032    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8425   -0.5462    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1889    1.0306    0.0000 H   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
  8  7  1  0  0  0  0
 10  9  1  0  0  0  0
 12  8  1  0  0  0  0
 12 11  2  0  0  0  0
 13  9  1  0  0  0  0
 14 11  1  0  0  0  0
 15 12  1  0  0  0  0
 16 14  2  0  0  0  0
 17 13  1  0  0  0  0
 18 16  1  0  0  0  0
 18 17  1  0  0  0  0
 19 15  2  0  0  0  0
 19 16  1  0  0  0  0
 20 15  1  0  0  0  0
 21  2  1  0  0  0  0
 21  3  1  0  0  0  0
 21 13  1  0  0  0  0
 21 18  1  0  0  0  0
 22  4  1  6  0  0  0
 22 10  1  0  0  0  0
 22 17  1  0  0  0  0
 23 19  1  0  0  0  0
 24 20  2  0  0  0  0
 25 20  1  0  0  0  0
 26 14  1  0  0  0  0
 26 22  1  0  0  0  0
 13 27  1  6  0  0  0
 17 28  1  6  0  0  0
 18 29  1  6  0  0  0
M  END

     RDKit          3D

 56 59  0  0  0  0  0  0  0  0999 V2000
    6.6655    0.6918   -1.2176 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5813    0.8230    0.2812 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1833    1.2166    0.6707 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2102    0.0587    0.1482 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9058    0.5020    0.5556 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6242   -0.1024    0.3702 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5703    0.7378    0.8589 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7383    0.4196    0.8105 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1077   -0.7726    0.2665 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1417   -1.6084   -0.2137 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4869   -2.8265   -0.7758 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2539   -1.2998   -0.1764 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1526   -2.2905   -0.7175 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5977   -3.3654   -1.1852 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4902   -2.3118   -0.8313 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5256   -1.1390    0.2135 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.3944   -0.5216    1.2727 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.4289   -0.2754    0.1669 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.9318    1.1052    0.3638 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0857    1.7839    1.3981 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9732    0.8042    1.7683 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.8910    0.8167    3.3016 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7478    1.2564    1.2928 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3686   -0.5131   -0.8455 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.7866    0.6969   -1.5254 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8015   -1.5225   -1.9103 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6337    1.1658   -1.5191 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8380    1.2940   -1.6561 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6529   -0.3603   -1.5410 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3491    1.4631    0.7138 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7475   -0.2125    0.7029 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8092    2.1168    0.1967 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1183    1.2444    1.7709 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4441   -0.0180   -0.9302 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6177   -0.7795    0.7472 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9622    0.8138    1.6767 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7922    1.5748    0.0747 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8334    1.7114    1.3056 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4020   -3.1544   -0.8726 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9635   -2.4809   -1.6997 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6833   -2.2558    0.2768 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7715   -1.1998    2.0617 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1721   -1.0974    0.1843 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9847    1.0245    0.7673 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0451    1.6963   -0.5747 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6900    2.0737    2.2856 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6504    2.7517    1.0207 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8390    0.7835    3.6418 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3403    1.7526    3.7092 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5044   -0.0189    3.7183 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0378    0.7376   -2.6102 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0718    1.6492   -1.0853 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6606    0.6152   -1.4943 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6078   -2.5595   -1.6030 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2495   -1.3528   -2.8654 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8769   -1.3425   -2.1592 H   0  0  0  0  0  0  0  0  0  0  0  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  1
 21 23  1  0
 23  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 10 12  2  0
 12 13  1  0
 13 15  1  0
 13 14  2  0
 12  6  1  0
  6  5  1  0
  5  4  1  0
  4  3  1  0
  3  2  1  0
  2  1  1  0
  6  7  2  0
  9 16  1  0
 16 17  1  0
 16 24  1  0
 24 25  1  6
 24 26  1  0
 17 18  1  0
 24 18  1  0
 17 21  1  0
  7  8  1  0
 18 43  1  6
 19 44  1  0
 19 45  1  0
 20 46  1  0
 20 47  1  0
 22 48  1  0
 22 49  1  0
 22 50  1  0
 11 39  1  0
 15 40  1  0
  5 36  1  0
  5 37  1  0
  4 34  1  0
  4 35  1  0
  3 32  1  0
  3 33  1  0
  2 30  1  0
  2 31  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
  7 38  1  0
 16 41  1  6
 17 42  1  1
 25 51  1  0
 25 52  1  0
 25 53  1  0
 26 54  1  0
 26 55  1  0
 26 56  1  0
M  END


  Mrv1652307312018222D          

 29 32  0  0  1  0            999 V2000
    7.5289   -0.9805    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4726    1.4890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6267    1.5293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8854   -1.7929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7895   -0.6146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1029   -1.0720    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3634   -0.7062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6769   -1.1636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1503   -0.2728    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1867   -1.0451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2509   -1.2552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9374   -0.7977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4687    0.3132    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5114   -0.8893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8846    0.0256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4586   -0.0660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1066   -0.1733    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7108    0.3583    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1451    0.3914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5711    0.4830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0702    0.9203    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0345   -0.9815    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0923    1.2147    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5183    1.3063    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3106    0.1171    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8031   -1.3418    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1079    0.9032    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8425   -0.5462    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1889    1.0306    0.0000 H   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
  8  7  1  0  0  0  0
 10  9  1  0  0  0  0
 12  8  1  0  0  0  0
 12 11  2  0  0  0  0
 13  9  1  0  0  0  0
 14 11  1  0  0  0  0
 15 12  1  0  0  0  0
 16 14  2  0  0  0  0
 17 13  1  0  0  0  0
 18 16  1  0  0  0  0
 18 17  1  0  0  0  0
 19 15  2  0  0  0  0
 19 16  1  0  0  0  0
 20 15  1  0  0  0  0
 21  2  1  0  0  0  0
 21  3  1  0  0  0  0
 21 13  1  0  0  0  0
 21 18  1  0  0  0  0
 22  4  1  6  0  0  0
 22 10  1  0  0  0  0
 22 17  1  0  0  0  0
 23 19  1  0  0  0  0
 24 20  2  0  0  0  0
 25 20  1  0  0  0  0
 26 14  1  0  0  0  0
 26 22  1  0  0  0  0
 13 27  1  6  0  0  0
 17 28  1  6  0  0  0
 18 29  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0044851

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@@]12CC[C@]3(C)OC4=C(C(O)=C(C(O)=O)C(CCCCC)=C4)[C@@]([H])([C@]13[H])C2(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C22H30O4/c1-5-6-7-8-12-11-14-16(19(23)15(12)20(24)25)18-17-13(21(18,2)3)9-10-22(17,4)26-14/h11,13,17-18,23H,5-10H2,1-4H3,(H,24,25)/t13-,17+,18+,22+/m1/s1

> <INCHI_KEY>
JVOHLEIRDMVLHS-NDONDOTQSA-N

> <FORMULA>
C22H30O4

> <MOLECULAR_WEIGHT>
358.478

> <EXACT_MASS>
358.214409446

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
56

> <JCHEM_AVERAGE_POLARIZABILITY>
40.948506037201824

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,9S,12R,14S)-3-hydroxy-9,13,13-trimethyl-5-pentyl-8-oxatetracyclo[7.4.1.0^{2,7}.0^{12,14}]tetradeca-2(7),3,5-triene-4-carboxylic acid

> <ALOGPS_LOGP>
5.22

> <JCHEM_LOGP>
5.969476210333333

> <ALOGPS_LOGS>
-4.60

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
13.303868109190624

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.911322331356541

> <JCHEM_PKA_STRONGEST_BASIC>
-4.904369323037083

> <JCHEM_POLAR_SURFACE_AREA>
66.76

> <JCHEM_REFRACTIVITY>
101.08219999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
9.00e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,9S,12R,14S)-3-hydroxy-9,13,13-trimethyl-5-pentyl-8-oxatetracyclo[7.4.1.0^{2,7}.0^{12,14}]tetradeca-2(7),3,5-triene-4-carboxylic 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      14.054  -1.830   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.882   2.779   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.037   2.855   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.653  -3.347   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      12.674  -1.147   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      11.392  -2.001   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      10.012  -1.318   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.730  -2.172   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.281  -0.509   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.349  -1.951   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.068  -2.343   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.350  -1.489   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.875   0.585   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.688  -1.660   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.251   0.048   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.589  -0.123   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.066  -0.323   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.193   0.669   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.871   0.731   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       8.533   0.902   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       1.998   1.718   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       1.931  -1.832   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       5.772   2.267   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       8.434   2.438   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0       9.913   0.219   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0       3.366  -2.505   0.000  0.00  0.00           O+0
HETATM   27  H   UNK     0      -0.201   1.686   0.000  0.00  0.00           H+0
HETATM   28  H   UNK     0       3.439  -1.020   0.000  0.00  0.00           H+0
HETATM   29  H   UNK     0       4.086   1.924   0.000  0.00  0.00           H+0
CONECT    1    5                                                            
CONECT    2   21                                                            
CONECT    3   21                                                            
CONECT    4   22                                                            
CONECT    5    1    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7   12                                                       
CONECT    9   10   13                                                       
CONECT   10    9   22                                                       
CONECT   11   12   14                                                       
CONECT   12    8   11   15                                                  
CONECT   13    9   17   21   27                                             
CONECT   14   11   16   26                                                  
CONECT   15   12   19   20                                                  
CONECT   16   14   18   19                                                  
CONECT   17   13   18   22   28                                             
CONECT   18   16   17   21   29                                             
CONECT   19   15   16   23                                                  
CONECT   20   15   24   25                                                  
CONECT   21    2    3   13   18                                             
CONECT   22    4   10   17   26                                             
CONECT   23   19                                                            
CONECT   24   20                                                            
CONECT   25   20                                                            
CONECT   26   14   22                                                       
CONECT   27   13                                                            
CONECT   28   17                                                            
CONECT   29   18                                                            
MASTER        0    0    0    0    0    0    0    0   29    0   64    0
END

View in JSmol

Synonyms

Value	Source
(1AR)-1a,2,3,3a,8bbeta,8cbeta-hexahydro-1,1,3abeta-trimethyl-6-pentyl-8-hydroxy-1H-4-oxa-benzo[F]cyclobuta[CD]indene-7-carboxylate	Generator

Chemical Formula

C₂₂H₃₀O₄

Average Mass

358.4780 Da

Monoisotopic Mass

358.21441 Da

IUPAC Name

(1S,9S,12R,14S)-3-hydroxy-9,13,13-trimethyl-5-pentyl-8-oxatetracyclo[7.4.1.0^{2,7}.0^{12,14}]tetradeca-2(7),3,5-triene-4-carboxylic acid

Traditional Name

(1S,9S,12R,14S)-3-hydroxy-9,13,13-trimethyl-5-pentyl-8-oxatetracyclo[7.4.1.0^{2,7}.0^{12,14}]tetradeca-2(7),3,5-triene-4-carboxylic acid

CAS Registry Number

Not Available

SMILES

[H][C@@]12CC[C@]3(C)OC4=C(C(O)=C(C(O)=O)C(CCCCC)=C4)[C@@]([H])([C@]13[H])C2(C)C

InChI Identifier

InChI=1S/C22H30O4/c1-5-6-7-8-12-11-14-16(19(23)15(12)20(24)25)18-17-13(21(18,2)3)9-10-22(17,4)26-14/h11,13,17-18,23H,5-10H2,1-4H3,(H,24,25)/t13-,17+,18+,22+/m1/s1

InChI Key

JVOHLEIRDMVLHS-NDONDOTQSA-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 salicylic acid and derivatives. Salicylic acid and derivatives are compounds containing a 2-hydroxybenzoic acid moiety or a derivative thereof.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Benzoic acids and derivatives

Direct Parent

Salicylic acid and derivatives

Alternative Parents

Substituents

Chromane
Benzopyran
Salicylic acid or derivatives
1-benzopyran
1-hydroxy-4-unsubstituted benzenoid
Alkyl aryl ether
Phenol
Vinylogous acid
Carboxylic acid derivative
Carboxylic acid
Ether
Oxacycle
Organoheterocyclic compound
Organic oxide
Organooxygen compound
Hydrocarbon derivative
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic 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	5.22	ALOGPS
logP	5.97	ChemAxon
logS	-4.6	ALOGPS
pKa (Strongest Acidic)	2.91	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	5	ChemAxon
Refractivity	101.08 m³·mol⁻¹	ChemAxon
Polarizability	40.95 Å³	ChemAxon
Number of Rings	4	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

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

101769204

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for Cannabicyclolic acid (NP0044851)

MOL for NP0044851 (Cannabicyclolic acid)

3D MOL for NP0044851 (Cannabicyclolic acid)

3D SDF for NP0044851 (Cannabicyclolic acid)

3D-SDF for NP0044851 (Cannabicyclolic acid)

PDB for NP0044851 (Cannabicyclolic acid)

3D PDB for NP0044851 (Cannabicyclolic acid)

SMILES for NP0044851 (Cannabicyclolic acid)

INCHI for NP0044851 (Cannabicyclolic acid)

Structure for NP0044851 (Cannabicyclolic acid)

3D Structure for NP0044851 (Cannabicyclolic acid)