NP-MRD: Showing NP-Card for 8-hydroxycannabinolic acid A (NP0034375)

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Record Information

Version

2.0

Created at

2021-06-20 18:07:21 UTC

Updated at

2021-06-30 00:04:43 UTC

NP-MRD ID

NP0034375

Secondary Accession Numbers

None

Natural Product Identification

Common Name

8-hydroxycannabinolic acid A

Provided By

JEOL Database JEOL Logo

Description

1,8-Dihydroxy-6,6,9-trimethyl-3-pentyl-6H-benzo[c]chromene-2-carboxylic acid belongs to the class of organic compounds known as dibenzopyrans. These are organic heterocyclic compounds with a structure containing a dibenzopyran moiety, made up of two benzene rings fused to a central pyran ring. 8-hydroxycannabinolic acid A is found in Cannabis sativa. 8-hydroxycannabinolic acid A was first documented in 2009 (Radwan, M. M., et al.). Based on a literature review very few articles have been published on 1,8-dihydroxy-6,6,9-trimethyl-3-pentyl-6H-benzo[c]chromene-2-carboxylic acid.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306202120073D          

 53 55  0  0  0  0            999 V2000
    5.7382    0.5588   -3.3033 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7665   -0.5684   -3.6147 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.9571   -0.9665   -2.3799 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9765   -2.0994   -2.7008 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2086   -2.5962   -1.4689 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2442   -1.5830   -0.8872 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6253   -0.9428    0.3004 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8169    0.0295    0.8922 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4349    0.3788    0.3703 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7952   -0.2261   -0.8565 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9612    0.1936   -1.4588 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0187   -1.2127   -1.4811 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4280   -1.8861   -2.7386 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1280   -2.9919   -3.1426 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2414   -1.1028   -3.4813 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2463    1.3503    1.1424 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6422    1.4936    1.0146 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3776    2.4422    1.7480 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8611    2.5412    1.5446 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6880    3.2598    2.6389 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2959    4.2259    3.3882 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3160    3.1184    2.8181 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5896    2.1504    2.1010 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9090    1.9542    2.3042 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3421    2.1684    3.7673 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7039    2.9245    1.4122 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3373    0.6005    2.0235 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3066    0.8275   -4.1992 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4494    0.2602   -2.5266 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2064    1.4511   -2.9580 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0901   -0.2490   -4.4161 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3270   -1.4333   -3.9880 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6388   -1.2845   -1.5817 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4109   -0.0905   -2.0117 H   0  0  0  0  0  0  0  0  0  0  0  0
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    2.9343   -2.8989   -0.7018 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.4004   -1.6576   -4.2791 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -5.2225    1.8026    0.8213 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.8256    3.7769    3.5293 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2298    3.2064    4.0958 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7640    1.5271    4.4436 H   0  0  0  0  0  0  0  0  0  0  0  0
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    1.4933    3.9698    1.6642 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7817    2.7527    1.5142 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4676    2.7857    0.3509 H   0  0  0  0  0  0  0  0  0  0  0  0
 18 20  1  0  0  0  0
  6 12  2  0  0  0  0
 20 22  2  0  0  0  0
 22 23  1  0  0  0  0
 18 19  1  0  0  0  0
  8 27  1  0  0  0  0
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  9 16  1  0  0  0  0
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  6  5  1  0  0  0  0
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  4  3  1  0  0  0  0
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  3  2  1  0  0  0  0
 16 17  1  0  0  0  0
  2  1  1  0  0  0  0
  7  6  1  0  0  0  0
 12 13  1  0  0  0  0
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 13 14  2  0  0  0  0
  7 39  1  0  0  0  0
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 21 46  1  0  0  0  0
 11 40  1  0  0  0  0
  5 37  1  0  0  0  0
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 25 48  1  0  0  0  0
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  4 35  1  0  0  0  0
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  3 33  1  0  0  0  0
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  2 31  1  0  0  0  0
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  1 28  1  0  0  0  0
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  1 30  1  0  0  0  0
 15 41  1  0  0  0  0
M  END

     RDKit          3D

 53 55  0  0  0  0  0  0  0  0999 V2000
    5.7382    0.5588   -3.3033 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.2086   -2.5962   -1.4689 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.7952   -0.2261   -0.8565 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.0187   -1.2127   -1.4811 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4280   -1.8861   -2.7386 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.8611    2.5412    1.5446 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.3160    3.1184    2.8181 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.9090    1.9542    2.3042 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3421    2.1684    3.7673 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1652306202120073D          

 53 55  0  0  0  0            999 V2000
    5.7382    0.5588   -3.3033 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7665   -0.5684   -3.6147 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.9571   -0.9665   -2.3799 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9765   -2.0994   -2.7008 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2086   -2.5962   -1.4689 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2442   -1.5830   -0.8872 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6253   -0.9428    0.3004 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.1902    0.8425    0.3382 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1253    3.5331    1.1640 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2225    1.8026    0.8213 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3857    2.3610    2.4884 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2426    4.2430    3.1804 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8256    3.7769    3.5293 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2298    3.2064    4.0958 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7640    1.5271    4.4436 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3947    1.8914    3.9043 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4933    3.9698    1.6642 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7817    2.7527    1.5142 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4676    2.7857    0.3509 H   0  0  0  0  0  0  0  0  0  0  0  0
 18 20  1  0  0  0  0
  6 12  2  0  0  0  0
 20 22  2  0  0  0  0
 22 23  1  0  0  0  0
 18 19  1  0  0  0  0
  8 27  1  0  0  0  0
 20 21  1  0  0  0  0
  9 16  1  0  0  0  0
 10 11  1  0  0  0  0
 23 24  1  0  0  0  0
  6  5  1  0  0  0  0
 24 27  1  0  0  0  0
 24 25  1  0  0  0  0
 12 10  1  0  0  0  0
 24 26  1  0  0  0  0
 10  9  2  0  0  0  0
  5  4  1  0  0  0  0
 23 16  2  0  0  0  0
  4  3  1  0  0  0  0
  8  9  1  0  0  0  0
  3  2  1  0  0  0  0
 16 17  1  0  0  0  0
  2  1  1  0  0  0  0
  7  6  1  0  0  0  0
 12 13  1  0  0  0  0
 17 18  2  0  0  0  0
 13 15  1  0  0  0  0
  8  7  2  0  0  0  0
 13 14  2  0  0  0  0
  7 39  1  0  0  0  0
 17 42  1  0  0  0  0
 22 47  1  0  0  0  0
 19 43  1  0  0  0  0
 19 44  1  0  0  0  0
 19 45  1  0  0  0  0
 21 46  1  0  0  0  0
 11 40  1  0  0  0  0
  5 37  1  0  0  0  0
  5 38  1  0  0  0  0
 25 48  1  0  0  0  0
 25 49  1  0  0  0  0
 25 50  1  0  0  0  0
 26 51  1  0  0  0  0
 26 52  1  0  0  0  0
 26 53  1  0  0  0  0
  4 35  1  0  0  0  0
  4 36  1  0  0  0  0
  3 33  1  0  0  0  0
  3 34  1  0  0  0  0
  2 31  1  0  0  0  0
  2 32  1  0  0  0  0
  1 28  1  0  0  0  0
  1 29  1  0  0  0  0
  1 30  1  0  0  0  0
 15 41  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0034375

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC(=O)C1=C(C([H])=C2OC(C3=C(C([H])=C(C(O[H])=C3[H])C([H])([H])[H])C2=C1O[H])(C([H])([H])[H])C([H])([H])[H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C22H26O5/c1-5-6-7-8-13-10-17-19(20(24)18(13)21(25)26)14-9-12(2)16(23)11-15(14)22(3,4)27-17/h9-11,23-24H,5-8H2,1-4H3,(H,25,26)

> <INCHI_KEY>
DMVDJDMFQCOKJW-UHFFFAOYSA-N

> <FORMULA>
C22H26O5

> <MOLECULAR_WEIGHT>
370.445

> <EXACT_MASS>
370.178023937

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
53

> <JCHEM_AVERAGE_POLARIZABILITY>
41.337923545880386

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
1,8-dihydroxy-6,6,9-trimethyl-3-pentyl-6H-benzo[c]chromene-2-carboxylic acid

> <ALOGPS_LOGP>
4.92

> <JCHEM_LOGP>
6.416748609999999

> <ALOGPS_LOGS>
-4.60

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
9.367007599253565

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.851899512018126

> <JCHEM_PKA_STRONGEST_BASIC>
-4.941723646153079

> <JCHEM_POLAR_SURFACE_AREA>
86.99000000000001

> <JCHEM_REFRACTIVITY>
104.9734

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
9.32e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1,8-dihydroxy-6,6,9-trimethyl-3-pentylbenzo[c]chromene-2-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 53 55  0  0  0  0  0  0  0  0999 V2000
    5.7382    0.5588   -3.3033 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7665   -0.5684   -3.6147 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9571   -0.9665   -2.3799 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9765   -2.0994   -2.7008 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2086   -2.5962   -1.4689 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2442   -1.5830   -0.8872 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6253   -0.9428    0.3004 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8169    0.0295    0.8922 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4349    0.3788    0.3703 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7952   -0.2261   -0.8565 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9612    0.1936   -1.4588 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0187   -1.2127   -1.4811 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4280   -1.8861   -2.7386 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1280   -2.9919   -3.1426 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2414   -1.1028   -3.4813 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2463    1.3503    1.1424 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6422    1.4936    1.0146 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3776    2.4422    1.7480 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8611    2.5412    1.5446 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6880    3.2598    2.6389 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2959    4.2259    3.3882 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3160    3.1184    2.8181 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5896    2.1504    2.1010 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9090    1.9542    2.3042 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3421    2.1684    3.7673 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7039    2.9245    1.4122 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3373    0.6005    2.0235 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3066    0.8275   -4.1992 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4494    0.2602   -2.5266 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2064    1.4511   -2.9580 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0901   -0.2490   -4.4161 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3270   -1.4333   -3.9880 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6388   -1.2845   -1.5817 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4109   -0.0905   -2.0117 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2854   -1.7687   -3.4841 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5381   -2.9466   -3.1144 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6709   -3.5210   -1.7033 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9343   -2.8989   -0.7018 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5766   -1.1819    0.7736 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9454   -0.0962   -2.3945 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4004   -1.6576   -4.2791 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1902    0.8425    0.3382 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1253    3.5331    1.1640 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2225    1.8026    0.8213 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3857    2.3610    2.4884 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2426    4.2430    3.1804 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8256    3.7769    3.5293 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2298    3.2064    4.0958 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7640    1.5271    4.4436 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3947    1.8914    3.9043 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4933    3.9698    1.6642 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7817    2.7527    1.5142 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4676    2.7857    0.3509 H   0  0  0  0  0  0  0  0  0  0  0  0
 18 20  1  0
  6 12  2  0
 20 22  2  0
 22 23  1  0
 18 19  1  0
  8 27  1  0
 20 21  1  0
  9 16  1  0
 10 11  1  0
 23 24  1  0
  6  5  1  0
 24 27  1  0
 24 25  1  0
 12 10  1  0
 24 26  1  0
 10  9  2  0
  5  4  1  0
 23 16  2  0
  4  3  1  0
  8  9  1  0
  3  2  1  0
 16 17  1  0
  2  1  1  0
  7  6  1  0
 12 13  1  0
 17 18  2  0
 13 15  1  0
  8  7  2  0
 13 14  2  0
  7 39  1  0
 17 42  1  0
 22 47  1  0
 19 43  1  0
 19 44  1  0
 19 45  1  0
 21 46  1  0
 11 40  1  0
  5 37  1  0
  5 38  1  0
 25 48  1  0
 25 49  1  0
 25 50  1  0
 26 51  1  0
 26 52  1  0
 26 53  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
 15 41  1  0
M  END

HEADER    PROTEIN                                 20-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-JUN-21         0                                  
HETATM    1  C   UNK     0       5.738   0.559  -3.303  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.766  -0.568  -3.615  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.957  -0.967  -2.380  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.977  -2.099  -2.701  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.209  -2.596  -1.469  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.244  -1.583  -0.887  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.625  -0.943   0.300  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.817   0.030   0.892  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.435   0.379   0.370  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.795  -0.226  -0.857  0.00  0.00           C+0
HETATM   11  O   UNK     0      -1.961   0.194  -1.459  0.00  0.00           O+0
HETATM   12  C   UNK     0       0.019  -1.213  -1.481  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.428  -1.886  -2.739  0.00  0.00           C+0
HETATM   14  O   UNK     0      -0.128  -2.992  -3.143  0.00  0.00           O+0
HETATM   15  O   UNK     0      -1.241  -1.103  -3.481  0.00  0.00           O+0
HETATM   16  C   UNK     0      -1.246   1.350   1.142  0.00  0.00           C+0
HETATM   17  C   UNK     0      -2.642   1.494   1.015  0.00  0.00           C+0
HETATM   18  C   UNK     0      -3.378   2.442   1.748  0.00  0.00           C+0
HETATM   19  C   UNK     0      -4.861   2.541   1.545  0.00  0.00           C+0
HETATM   20  C   UNK     0      -2.688   3.260   2.639  0.00  0.00           C+0
HETATM   21  O   UNK     0      -3.296   4.226   3.388  0.00  0.00           O+0
HETATM   22  C   UNK     0      -1.316   3.118   2.818  0.00  0.00           C+0
HETATM   23  C   UNK     0      -0.590   2.150   2.101  0.00  0.00           C+0
HETATM   24  C   UNK     0       0.909   1.954   2.304  0.00  0.00           C+0
HETATM   25  C   UNK     0       1.342   2.168   3.767  0.00  0.00           C+0
HETATM   26  C   UNK     0       1.704   2.925   1.412  0.00  0.00           C+0
HETATM   27  O   UNK     0       1.337   0.601   2.023  0.00  0.00           O+0
HETATM   28  H   UNK     0       6.307   0.828  -4.199  0.00  0.00           H+0
HETATM   29  H   UNK     0       6.449   0.260  -2.527  0.00  0.00           H+0
HETATM   30  H   UNK     0       5.206   1.451  -2.958  0.00  0.00           H+0
HETATM   31  H   UNK     0       4.090  -0.249  -4.416  0.00  0.00           H+0
HETATM   32  H   UNK     0       5.327  -1.433  -3.988  0.00  0.00           H+0
HETATM   33  H   UNK     0       4.639  -1.285  -1.582  0.00  0.00           H+0
HETATM   34  H   UNK     0       3.411  -0.091  -2.012  0.00  0.00           H+0
HETATM   35  H   UNK     0       2.285  -1.769  -3.484  0.00  0.00           H+0
HETATM   36  H   UNK     0       3.538  -2.947  -3.114  0.00  0.00           H+0
HETATM   37  H   UNK     0       1.671  -3.521  -1.703  0.00  0.00           H+0
HETATM   38  H   UNK     0       2.934  -2.899  -0.702  0.00  0.00           H+0
HETATM   39  H   UNK     0       2.577  -1.182   0.774  0.00  0.00           H+0
HETATM   40  H   UNK     0      -1.945  -0.096  -2.394  0.00  0.00           H+0
HETATM   41  H   UNK     0      -1.400  -1.658  -4.279  0.00  0.00           H+0
HETATM   42  H   UNK     0      -3.190   0.843   0.338  0.00  0.00           H+0
HETATM   43  H   UNK     0      -5.125   3.533   1.164  0.00  0.00           H+0
HETATM   44  H   UNK     0      -5.223   1.803   0.821  0.00  0.00           H+0
HETATM   45  H   UNK     0      -5.386   2.361   2.488  0.00  0.00           H+0
HETATM   46  H   UNK     0      -4.243   4.243   3.180  0.00  0.00           H+0
HETATM   47  H   UNK     0      -0.826   3.777   3.529  0.00  0.00           H+0
HETATM   48  H   UNK     0       1.230   3.206   4.096  0.00  0.00           H+0
HETATM   49  H   UNK     0       0.764   1.527   4.444  0.00  0.00           H+0
HETATM   50  H   UNK     0       2.395   1.891   3.904  0.00  0.00           H+0
HETATM   51  H   UNK     0       1.493   3.970   1.664  0.00  0.00           H+0
HETATM   52  H   UNK     0       2.782   2.753   1.514  0.00  0.00           H+0
HETATM   53  H   UNK     0       1.468   2.786   0.351  0.00  0.00           H+0
CONECT    1    2   28   29   30                                             
CONECT    2    3    1   31   32                                             
CONECT    3    4    2   33   34                                             
CONECT    4    5    3   35   36                                             
CONECT    5    6    4   37   38                                             
CONECT    6   12    5    7                                                  
CONECT    7    6    8   39                                                  
CONECT    8   27    9    7                                                  
CONECT    9   16   10    8                                                  
CONECT   10   11   12    9                                                  
CONECT   11   10   40                                                       
CONECT   12    6   10   13                                                  
CONECT   13   12   15   14                                                  
CONECT   14   13                                                            
CONECT   15   13   41                                                       
CONECT   16    9   23   17                                                  
CONECT   17   16   18   42                                                  
CONECT   18   20   19   17                                                  
CONECT   19   18   43   44   45                                             
CONECT   20   18   22   21                                                  
CONECT   21   20   46                                                       
CONECT   22   20   23   47                                                  
CONECT   23   22   24   16                                                  
CONECT   24   23   27   25   26                                             
CONECT   25   24   48   49   50                                             
CONECT   26   24   51   52   53                                             
CONECT   27    8   24                                                       
CONECT   28    1                                                            
CONECT   29    1                                                            
CONECT   30    1                                                            
CONECT   31    2                                                            
CONECT   32    2                                                            
CONECT   33    3                                                            
CONECT   34    3                                                            
CONECT   35    4                                                            
CONECT   36    4                                                            
CONECT   37    5                                                            
CONECT   38    5                                                            
CONECT   39    7                                                            
CONECT   40   11                                                            
CONECT   41   15                                                            
CONECT   42   17                                                            
CONECT   43   19                                                            
CONECT   44   19                                                            
CONECT   45   19                                                            
CONECT   46   21                                                            
CONECT   47   22                                                            
CONECT   48   25                                                            
CONECT   49   25                                                            
CONECT   50   25                                                            
CONECT   51   26                                                            
CONECT   52   26                                                            
CONECT   53   26                                                            
MASTER        0    0    0    0    0    0    0    0   53    0  110    0
END

RDKit          3D

53 55  0  0  0  0  0  0  0  0999 V2000
    5.7382    0.5588   -3.3033 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7665   -0.5684   -3.6147 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9571   -0.9665   -2.3799 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9765   -2.0994   -2.7008 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2086   -2.5962   -1.4689 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2442   -1.5830   -0.8872 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6253   -0.9428    0.3004 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8169    0.0295    0.8922 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4349    0.3788    0.3703 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7952   -0.2261   -0.8565 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9612    0.1936   -1.4588 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0187   -1.2127   -1.4811 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4280   -1.8861   -2.7386 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1280   -2.9919   -3.1426 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2414   -1.1028   -3.4813 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2463    1.3503    1.1424 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6422    1.4936    1.0146 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3776    2.4422    1.7480 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8611    2.5412    1.5446 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6880    3.2598    2.6389 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2959    4.2259    3.3882 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3160    3.1184    2.8181 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5896    2.1504    2.1010 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9090    1.9542    2.3042 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3421    2.1684    3.7673 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7039    2.9245    1.4122 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3373    0.6005    2.0235 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3066    0.8275   -4.1992 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4494    0.2602   -2.5266 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2064    1.4511   -2.9580 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0901   -0.2490   -4.4161 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3270   -1.4333   -3.9880 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6388   -1.2845   -1.5817 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4109   -0.0905   -2.0117 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2854   -1.7687   -3.4841 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5381   -2.9466   -3.1144 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6709   -3.5210   -1.7033 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9343   -2.8989   -0.7018 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5766   -1.1819    0.7736 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9454   -0.0962   -2.3945 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4004   -1.6576   -4.2791 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1902    0.8425    0.3382 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1253    3.5331    1.1640 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2225    1.8026    0.8213 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3857    2.3610    2.4884 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2426    4.2430    3.1804 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8256    3.7769    3.5293 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2298    3.2064    4.0958 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7640    1.5271    4.4436 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3947    1.8914    3.9043 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4933    3.9698    1.6642 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7817    2.7527    1.5142 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4676    2.7857    0.3509 H   0  0  0  0  0  0  0  0  0  0  0  0
 18 20  1  0
  6 12  2  0
 20 22  2  0
 22 23  1  0
 18 19  1  0
  8 27  1  0
 20 21  1  0
  9 16  1  0
 10 11  1  0
 23 24  1  0
  6  5  1  0
 24 27  1  0
 24 25  1  0
 12 10  1  0
 24 26  1  0
 10  9  2  0
  5  4  1  0
 23 16  2  0
  4  3  1  0
  8  9  1  0
  3  2  1  0
 16 17  1  0
  2  1  1  0
  7  6  1  0
 12 13  1  0
 17 18  2  0
 13 15  1  0
  8  7  2  0
 13 14  2  0
  7 39  1  0
 17 42  1  0
 22 47  1  0
 19 43  1  0
 19 44  1  0
 19 45  1  0
 21 46  1  0
 11 40  1  0
  5 37  1  0
  5 38  1  0
 25 48  1  0
 25 49  1  0
 25 50  1  0
 26 51  1  0
 26 52  1  0
 26 53  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
 15 41  1  0
M  END

View in JSmol View DFT Assignments 3D Conformers

Synonyms

Value	Source
1,8-Dihydroxy-6,6,9-trimethyl-3-pentyl-6H-benzo[c]chromene-2-carboxylate	Generator
8-Hydroxycannabinolate a	Generator

Chemical Formula

C₂₂H₂₆O₅

Average Mass

370.4450 Da

Monoisotopic Mass

370.17802 Da

IUPAC Name

1,8-dihydroxy-6,6,9-trimethyl-3-pentyl-6H-benzo[c]chromene-2-carboxylic acid

Traditional Name

1,8-dihydroxy-6,6,9-trimethyl-3-pentylbenzo[c]chromene-2-carboxylic acid

CAS Registry Number

Not Available

SMILES

[H]OC(=O)C1=C(C([H])=C2OC(C3=C(C([H])=C(C(O[H])=C3[H])C([H])([H])[H])C2=C1O[H])(C([H])([H])[H])C([H])([H])[H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H]

InChI Identifier

InChI=1S/C22H26O5/c1-5-6-7-8-13-10-17-19(20(24)18(13)21(25)26)14-9-12(2)16(23)11-15(14)22(3,4)27-17/h9-11,23-24H,5-8H2,1-4H3,(H,25,26)

InChI Key

DMVDJDMFQCOKJW-UHFFFAOYSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 125 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 150 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 175 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 225 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 250 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, chcl3, 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	JEOL database	Radwan, M. M., et al, J. Nat. Prod. 72, 906 (2009)

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as dibenzopyrans. These are organic heterocyclic compounds with a structure containing a dibenzopyran moiety, made up of two benzene rings fused to a central pyran ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzopyrans

Sub Class

1-benzopyrans

Direct Parent

Dibenzopyrans

Alternative Parents

Substituents

Dibenzopyran
Hydroxybenzoic acid
Salicylic acid or derivatives
2-benzopyran
Phenol
Alkyl aryl ether
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Benzenoid
Vinylogous acid
Oxacycle
Carboxylic acid derivative
Ether
Carboxylic acid
Hydrocarbon derivative
Organooxygen compound
Organic oxide
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	4.92	ALOGPS
logP	6.42	ChemAxon
logS	-4.6	ALOGPS
pKa (Strongest Acidic)	2.85	ChemAxon
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	86.99 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	104.97 m³·mol⁻¹	ChemAxon
Polarizability	41.34 Å³	ChemAxon
Number of Rings	3	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

24625385

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

44139742

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Radwan, M. M., et al. (2009). Radwan, M. M., et al, J. Nat. Prod. 72, 906 (2009). J. Nat. Prod..

Showing NP-Card for 8-hydroxycannabinolic acid A (NP0034375)

MOL for NP0034375 (8-hydroxycannabinolic acid A)

3D MOL for NP0034375 (8-hydroxycannabinolic acid A)

3D SDF for NP0034375 (8-hydroxycannabinolic acid A)

3D-SDF for NP0034375 (8-hydroxycannabinolic acid A)

PDB for NP0034375 (8-hydroxycannabinolic acid A)

3D PDB for NP0034375 (8-hydroxycannabinolic acid A)

SMILES for NP0034375 (8-hydroxycannabinolic acid A)

INCHI for NP0034375 (8-hydroxycannabinolic acid A)

Structure for NP0034375 (8-hydroxycannabinolic acid A)

3D Structure for NP0034375 (8-hydroxycannabinolic acid A)