NP-MRD: Showing NP-Card for (-)-7R-cannabicoumarononic acid A (NP0034370)

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Record Information

Version

2.0

Created at

2021-06-20 18:07:09 UTC

Updated at

2021-06-30 00:04:43 UTC

NP-MRD ID

NP0034370

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(-)-7R-cannabicoumarononic acid A

Provided By

JEOL Database JEOL Logo

Description

(3R)-3-(3-Oxobutyl)-4,4-dimethyl-7-pentyl-3,4-dihydro-1,5-dioxaacenaphthylene-8-carboxylic acid belongs to the class of organic compounds known as 1-benzopyrans. These are organic aromatic compounds that 1-benzopyran, a bicyclic compound made up of a benzene ring fused to a pyran, so that the oxygen atom is at the 1-position. (-)-7R-cannabicoumarononic acid A is found in Cannabis sativa. (-)-7R-cannabicoumarononic acid A was first documented in 2009 (Radwan, M. M., et al.). Based on a literature review very few articles have been published on (3R)-3-(3-Oxobutyl)-4,4-dimethyl-7-pentyl-3,4-dihydro-1,5-dioxaacenaphthylene-8-carboxylic acid.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306202120073D          

 55 57  0  0  0  0            999 V2000
   -2.4921    3.6284   -4.3136 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5670    2.4858   -4.7015 C   0  0  2  0  0  0  0  0  0  0  0  0
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    0.2091    0.8738   -3.9099 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1578    0.4447   -2.7837 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4540   -0.2274   -1.6202 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0830   -1.5899   -1.7858 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5873   -2.2737   -0.7786 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9163   -1.5681    0.3646 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6161   -2.0200    1.4867 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6012   -0.9723    2.3746 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9710    0.1126    1.8146 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.1443   -3.4213    1.4370 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.6303   -3.4340    0.9860 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.5999   -2.6209    1.8503 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.7307   -3.1332    3.2728 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.2367   -4.1974    3.6427 O   0  0  0  0  0  0  0  0  0  0  0  0
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  6 14  2  0  0  0  0
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  7  6  1  0  0  0  0
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  8  7  2  0  0  0  0
 18 42  1  1  0  0  0
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M  END

     RDKit          3D

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   -1.6012   -0.9723    2.3746 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1652306202120073D          

 55 57  0  0  0  0            999 V2000
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   -1.5670    2.4858   -4.7015 C   0  0  2  0  0  0  0  0  0  0  0  0
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   -1.3802    1.7151   -2.7012 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3909    0.0196   -4.2472 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8195    1.1870   -4.7663 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8850   -0.2690   -3.1944 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7620    1.2958   -2.4600 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3301   -2.1196   -2.7037 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9776   -0.8192    3.3765 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2073    3.4795    0.4154 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0585   -3.8788    2.4291 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7025   -3.0607   -0.0439 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9945   -4.4679    0.9719 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3127   -1.5661    1.8776 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5983   -2.6745    1.4000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0610   -1.2924    4.3061 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5573   -2.7426    5.2068 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5524   -2.1747    3.8459 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8093   -5.1198    0.3876 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0274   -5.1822    1.9836 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7055   -3.6699    1.3622 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1436   -6.2198   -0.5401 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1322   -6.1775    0.9337 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7177   -5.4726   -0.5981 H   0  0  0  0  0  0  0  0  0  0  0  0
  6 14  2  0  0  0  0
  6  5  1  0  0  0  0
  5  4  1  0  0  0  0
 14 13  1  0  0  0  0
  4  3  1  0  0  0  0
 13  9  2  0  0  0  0
  3  2  1  0  0  0  0
  8 27  1  0  0  0  0
  2  1  1  0  0  0  0
  9 10  1  0  0  0  0
 14 15  1  0  0  0  0
 10 18  1  0  0  0  0
 15 17  1  0  0  0  0
 18 24  1  0  0  0  0
 15 16  2  0  0  0  0
 24 27  1  0  0  0  0
 10 11  2  0  0  0  0
 12 11  1  0  0  0  0
  8  9  1  0  0  0  0
 18 19  1  0  0  0  0
 24 25  1  1  0  0  0
 19 20  1  0  0  0  0
  7  6  1  0  0  0  0
 20 21  1  0  0  0  0
 24 26  1  0  0  0  0
 21 22  1  0  0  0  0
  8  7  2  0  0  0  0
 18 42  1  1  0  0  0
 13 12  1  0  0  0  0
 21 23  2  0  0  0  0
  7 39  1  0  0  0  0
 25 50  1  0  0  0  0
 25 51  1  0  0  0  0
 25 52  1  0  0  0  0
 26 53  1  0  0  0  0
 26 54  1  0  0  0  0
 26 55  1  0  0  0  0
  5 37  1  0  0  0  0
  5 38  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
 17 41  1  0  0  0  0
 11 40  1  0  0  0  0
 19 43  1  0  0  0  0
 19 44  1  0  0  0  0
 20 45  1  0  0  0  0
 20 46  1  0  0  0  0
 22 47  1  0  0  0  0
 22 48  1  0  0  0  0
 22 49  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0034370

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC(=O)C1=C(C([H])=C2OC(C([H])([H])[H])(C([H])([H])[H])[C@@]([H])(C3=C([H])OC1=C23)C([H])([H])C([H])([H])C(=O)C([H])([H])[H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C22H28O5/c1-5-6-7-8-14-11-17-19-15(12-26-20(19)18(14)21(24)25)16(10-9-13(2)23)22(3,4)27-17/h11-12,16H,5-10H2,1-4H3,(H,24,25)/t16-/m1/s1

> <INCHI_KEY>
WEYZBZCYDDIMCS-MRXNPFEDSA-N

> <FORMULA>
C22H28O5

> <MOLECULAR_WEIGHT>
372.461

> <EXACT_MASS>
372.193674002

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
55

> <JCHEM_AVERAGE_POLARIZABILITY>
41.36134604211925

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(5R)-6,6-dimethyl-5-(3-oxobutyl)-10-pentyl-2,7-dioxatricyclo[6.3.1.0^{4,12}]dodeca-1(12),3,8,10-tetraene-11-carboxylic acid

> <ALOGPS_LOGP>
4.62

> <JCHEM_LOGP>
4.9245110216666665

> <ALOGPS_LOGS>
-4.65

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
19.49801880708486

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.111511058122435

> <JCHEM_PKA_STRONGEST_BASIC>
-2.890355590602404

> <JCHEM_POLAR_SURFACE_AREA>
76.74

> <JCHEM_REFRACTIVITY>
103.3204

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.30e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(5R)-6,6-dimethyl-5-(3-oxobutyl)-10-pentyl-2,7-dioxatricyclo[6.3.1.0^{4,12}]dodeca-1(12),3,8,10-tetraene-11-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 55 57  0  0  0  0  0  0  0  0999 V2000
   -2.4921    3.6284   -4.3136 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5670    2.4858   -4.7015 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7172    2.0275   -3.5158 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2091    0.8738   -3.9099 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1578    0.4447   -2.7837 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4540   -0.2274   -1.6202 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0830   -1.5899   -1.7858 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5873   -2.2737   -0.7786 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9163   -1.5681    0.3646 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6161   -2.0200    1.4867 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6012   -0.9723    2.3746 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9710    0.1126    1.8146 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5557   -0.2573    0.5575 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1334    0.4685   -0.4148 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4927    1.8703   -0.1633 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5754    2.3886   -0.3553 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5626    2.5780    0.2756 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1443   -3.4213    1.4370 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.6303   -3.4340    0.9860 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5999   -2.6209    1.8503 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7307   -3.1332    3.2728 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5301   -2.2755    4.2184 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2367   -4.1974    3.6427 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2039   -4.2583    0.4184 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1582   -4.5752    1.0814 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8415   -5.6085    0.0448 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9441   -3.5974   -0.8799 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9208    4.4943   -3.9642 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1779    3.3245   -3.5163 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0902    3.9410   -5.1753 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9175    2.8120   -5.5220 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1671    1.6480   -5.0754 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1197    2.8699   -3.1468 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3802    1.7151   -2.7012 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3909    0.0196   -4.2472 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8195    1.1870   -4.7663 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8850   -0.2690   -3.1944 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7620    1.2958   -2.4600 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3301   -2.1196   -2.7037 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9776   -0.8192    3.3765 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2073    3.4795    0.4154 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0585   -3.8788    2.4291 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7025   -3.0607   -0.0439 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9945   -4.4679    0.9719 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3127   -1.5661    1.8776 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5983   -2.6745    1.4000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0610   -1.2924    4.3061 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5573   -2.7426    5.2068 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5524   -2.1747    3.8459 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8093   -5.1198    0.3876 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0274   -5.1822    1.9836 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7055   -3.6699    1.3622 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1436   -6.2198   -0.5401 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1322   -6.1775    0.9337 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7177   -5.4726   -0.5981 H   0  0  0  0  0  0  0  0  0  0  0  0
  6 14  2  0
  6  5  1  0
  5  4  1  0
 14 13  1  0
  4  3  1  0
 13  9  2  0
  3  2  1  0
  8 27  1  0
  2  1  1  0
  9 10  1  0
 14 15  1  0
 10 18  1  0
 15 17  1  0
 18 24  1  0
 15 16  2  0
 24 27  1  0
 10 11  2  0
 12 11  1  0
  8  9  1  0
 18 19  1  0
 24 25  1  1
 19 20  1  0
  7  6  1  0
 20 21  1  0
 24 26  1  0
 21 22  1  0
  8  7  2  0
 18 42  1  1
 13 12  1  0
 21 23  2  0
  7 39  1  0
 25 50  1  0
 25 51  1  0
 25 52  1  0
 26 53  1  0
 26 54  1  0
 26 55  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
 17 41  1  0
 11 40  1  0
 19 43  1  0
 19 44  1  0
 20 45  1  0
 20 46  1  0
 22 47  1  0
 22 48  1  0
 22 49  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      -2.492   3.628  -4.314  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.567   2.486  -4.702  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.717   2.027  -3.516  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.209   0.874  -3.910  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.158   0.445  -2.784  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.454  -0.227  -1.620  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.083  -1.590  -1.786  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.587  -2.274  -0.779  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.916  -1.568   0.365  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.616  -2.020   1.487  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.601  -0.972   2.375  0.00  0.00           C+0
HETATM   12  O   UNK     0      -0.971   0.113   1.815  0.00  0.00           O+0
HETATM   13  C   UNK     0      -0.556  -0.257   0.558  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.133   0.469  -0.415  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.493   1.870  -0.163  0.00  0.00           C+0
HETATM   16  O   UNK     0       1.575   2.389  -0.355  0.00  0.00           O+0
HETATM   17  O   UNK     0      -0.563   2.578   0.276  0.00  0.00           O+0
HETATM   18  C   UNK     0      -2.144  -3.421   1.437  0.00  0.00           C+0
HETATM   19  C   UNK     0      -3.630  -3.434   0.986  0.00  0.00           C+0
HETATM   20  C   UNK     0      -4.600  -2.621   1.850  0.00  0.00           C+0
HETATM   21  C   UNK     0      -4.731  -3.133   3.273  0.00  0.00           C+0
HETATM   22  C   UNK     0      -5.530  -2.276   4.218  0.00  0.00           C+0
HETATM   23  O   UNK     0      -4.237  -4.197   3.643  0.00  0.00           O+0
HETATM   24  C   UNK     0      -1.204  -4.258   0.418  0.00  0.00           C+0
HETATM   25  C   UNK     0       0.158  -4.575   1.081  0.00  0.00           C+0
HETATM   26  C   UNK     0      -1.841  -5.609   0.045  0.00  0.00           C+0
HETATM   27  O   UNK     0      -0.944  -3.597  -0.880  0.00  0.00           O+0
HETATM   28  H   UNK     0      -1.921   4.494  -3.964  0.00  0.00           H+0
HETATM   29  H   UNK     0      -3.178   3.325  -3.516  0.00  0.00           H+0
HETATM   30  H   UNK     0      -3.090   3.941  -5.175  0.00  0.00           H+0
HETATM   31  H   UNK     0      -0.918   2.812  -5.522  0.00  0.00           H+0
HETATM   32  H   UNK     0      -2.167   1.648  -5.075  0.00  0.00           H+0
HETATM   33  H   UNK     0      -0.120   2.870  -3.147  0.00  0.00           H+0
HETATM   34  H   UNK     0      -1.380   1.715  -2.701  0.00  0.00           H+0
HETATM   35  H   UNK     0      -0.391   0.020  -4.247  0.00  0.00           H+0
HETATM   36  H   UNK     0       0.820   1.187  -4.766  0.00  0.00           H+0
HETATM   37  H   UNK     0       1.885  -0.269  -3.194  0.00  0.00           H+0
HETATM   38  H   UNK     0       1.762   1.296  -2.460  0.00  0.00           H+0
HETATM   39  H   UNK     0       0.330  -2.120  -2.704  0.00  0.00           H+0
HETATM   40  H   UNK     0      -1.978  -0.819   3.377  0.00  0.00           H+0
HETATM   41  H   UNK     0      -0.207   3.479   0.415  0.00  0.00           H+0
HETATM   42  H   UNK     0      -2.059  -3.879   2.429  0.00  0.00           H+0
HETATM   43  H   UNK     0      -3.703  -3.061  -0.044  0.00  0.00           H+0
HETATM   44  H   UNK     0      -3.994  -4.468   0.972  0.00  0.00           H+0
HETATM   45  H   UNK     0      -4.313  -1.566   1.878  0.00  0.00           H+0
HETATM   46  H   UNK     0      -5.598  -2.675   1.400  0.00  0.00           H+0
HETATM   47  H   UNK     0      -5.061  -1.292   4.306  0.00  0.00           H+0
HETATM   48  H   UNK     0      -5.557  -2.743   5.207  0.00  0.00           H+0
HETATM   49  H   UNK     0      -6.552  -2.175   3.846  0.00  0.00           H+0
HETATM   50  H   UNK     0       0.809  -5.120   0.388  0.00  0.00           H+0
HETATM   51  H   UNK     0       0.027  -5.182   1.984  0.00  0.00           H+0
HETATM   52  H   UNK     0       0.706  -3.670   1.362  0.00  0.00           H+0
HETATM   53  H   UNK     0      -1.144  -6.220  -0.540  0.00  0.00           H+0
HETATM   54  H   UNK     0      -2.132  -6.178   0.934  0.00  0.00           H+0
HETATM   55  H   UNK     0      -2.718  -5.473  -0.598  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   14    5    7                                                  
CONECT    7    6    8   39                                                  
CONECT    8   27    9    7                                                  
CONECT    9   13   10    8                                                  
CONECT   10    9   18   11                                                  
CONECT   11   10   12   40                                                  
CONECT   12   11   13                                                       
CONECT   13   14    9   12                                                  
CONECT   14    6   13   15                                                  
CONECT   15   14   17   16                                                  
CONECT   16   15                                                            
CONECT   17   15   41                                                       
CONECT   18   10   24   19   42                                             
CONECT   19   18   20   43   44                                             
CONECT   20   19   21   45   46                                             
CONECT   21   20   22   23                                                  
CONECT   22   21   47   48   49                                             
CONECT   23   21                                                            
CONECT   24   18   27   25   26                                             
CONECT   25   24   50   51   52                                             
CONECT   26   24   53   54   55                                             
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   17                                                            
CONECT   42   18                                                            
CONECT   43   19                                                            
CONECT   44   19                                                            
CONECT   45   20                                                            
CONECT   46   20                                                            
CONECT   47   22                                                            
CONECT   48   22                                                            
CONECT   49   22                                                            
CONECT   50   25                                                            
CONECT   51   25                                                            
CONECT   52   25                                                            
CONECT   53   26                                                            
CONECT   54   26                                                            
CONECT   55   26                                                            
MASTER        0    0    0    0    0    0    0    0   55    0  114    0
END

RDKit          3D

55 57  0  0  0  0  0  0  0  0999 V2000
   -2.4921    3.6284   -4.3136 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5670    2.4858   -4.7015 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7172    2.0275   -3.5158 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2091    0.8738   -3.9099 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1578    0.4447   -2.7837 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4540   -0.2274   -1.6202 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0830   -1.5899   -1.7858 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5873   -2.2737   -0.7786 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9163   -1.5681    0.3646 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6161   -2.0200    1.4867 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6012   -0.9723    2.3746 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9710    0.1126    1.8146 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5557   -0.2573    0.5575 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1334    0.4685   -0.4148 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4927    1.8703   -0.1633 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5754    2.3886   -0.3553 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5626    2.5780    0.2756 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1443   -3.4213    1.4370 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.6303   -3.4340    0.9860 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5999   -2.6209    1.8503 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7307   -3.1332    3.2728 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5301   -2.2755    4.2184 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2367   -4.1974    3.6427 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2039   -4.2583    0.4184 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1582   -4.5752    1.0814 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8415   -5.6085    0.0448 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9441   -3.5974   -0.8799 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9208    4.4943   -3.9642 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1779    3.3245   -3.5163 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0902    3.9410   -5.1753 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9175    2.8120   -5.5220 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1671    1.6480   -5.0754 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1197    2.8699   -3.1468 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3802    1.7151   -2.7012 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3909    0.0196   -4.2472 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8195    1.1870   -4.7663 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8850   -0.2690   -3.1944 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7620    1.2958   -2.4600 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3301   -2.1196   -2.7037 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9776   -0.8192    3.3765 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2073    3.4795    0.4154 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0585   -3.8788    2.4291 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7025   -3.0607   -0.0439 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9945   -4.4679    0.9719 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3127   -1.5661    1.8776 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5983   -2.6745    1.4000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0610   -1.2924    4.3061 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5573   -2.7426    5.2068 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5524   -2.1747    3.8459 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8093   -5.1198    0.3876 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0274   -5.1822    1.9836 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7055   -3.6699    1.3622 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1436   -6.2198   -0.5401 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1322   -6.1775    0.9337 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7177   -5.4726   -0.5981 H   0  0  0  0  0  0  0  0  0  0  0  0
  6 14  2  0
  6  5  1  0
  5  4  1  0
 14 13  1  0
  4  3  1  0
 13  9  2  0
  3  2  1  0
  8 27  1  0
  2  1  1  0
  9 10  1  0
 14 15  1  0
 10 18  1  0
 15 17  1  0
 18 24  1  0
 15 16  2  0
 24 27  1  0
 10 11  2  0
 12 11  1  0
  8  9  1  0
 18 19  1  0
 24 25  1  1
 19 20  1  0
  7  6  1  0
 20 21  1  0
 24 26  1  0
 21 22  1  0
  8  7  2  0
 18 42  1  1
 13 12  1  0
 21 23  2  0
  7 39  1  0
 25 50  1  0
 25 51  1  0
 25 52  1  0
 26 53  1  0
 26 54  1  0
 26 55  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
 17 41  1  0
 11 40  1  0
 19 43  1  0
 19 44  1  0
 20 45  1  0
 20 46  1  0
 22 47  1  0
 22 48  1  0
 22 49  1  0
M  END

View in JSmol View DFT Assignments 3D Conformers

Synonyms

Value	Source
(3R)-3-(3-Oxobutyl)-4,4-dimethyl-7-pentyl-3,4-dihydro-1,5-dioxaacenaphthylene-8-carboxylate	Generator

Chemical Formula

C₂₂H₂₈O₅

Average Mass

372.4610 Da

Monoisotopic Mass

372.19367 Da

IUPAC Name

(5R)-6,6-dimethyl-5-(3-oxobutyl)-10-pentyl-2,7-dioxatricyclo[6.3.1.0^{4,12}]dodeca-1(12),3,8,10-tetraene-11-carboxylic acid

Traditional Name

(5R)-6,6-dimethyl-5-(3-oxobutyl)-10-pentyl-2,7-dioxatricyclo[6.3.1.0^{4,12}]dodeca-1(12),3,8,10-tetraene-11-carboxylic acid

CAS Registry Number

Not Available

SMILES

[H]OC(=O)C1=C(C([H])=C2OC(C([H])([H])[H])(C([H])([H])[H])[C@@]([H])(C3=C([H])OC1=C23)C([H])([H])C([H])([H])C(=O)C([H])([H])[H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H]

InChI Identifier

InChI=1S/C22H28O5/c1-5-6-7-8-14-11-17-19-15(12-26-20(19)18(14)21(24)25)16(10-9-13(2)23)22(3,4)27-17/h11-12,16H,5-10H2,1-4H3,(H,24,25)/t16-/m1/s1

InChI Key

WEYZBZCYDDIMCS-MRXNPFEDSA-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 1-benzopyrans. These are organic aromatic compounds that 1-benzopyran, a bicyclic compound made up of a benzene ring fused to a pyran, so that the oxygen atom is at the 1-position.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzopyrans

Sub Class

1-benzopyrans

Direct Parent

1-benzopyrans

Alternative Parents

Substituents

1-benzopyran
Benzofuran
Alkyl aryl ether
Benzenoid
Furan
Heteroaromatic compound
Ketone
Carboxylic acid derivative
Carboxylic acid
Ether
Oxacycle
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Carbonyl group
Organooxygen 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	4.62	ALOGPS
logP	4.92	ChemAxon
logS	-4.6	ALOGPS
pKa (Strongest Acidic)	4.11	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	76.74 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	103.32 m³·mol⁻¹	ChemAxon
Polarizability	41.36 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	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

44139614

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 (-)-7R-cannabicoumarononic acid A (NP0034370)

MOL for NP0034370 ((-)-7R-cannabicoumarononic acid A)

3D MOL for NP0034370 ((-)-7R-cannabicoumarononic acid A)

3D SDF for NP0034370 ((-)-7R-cannabicoumarononic acid A)

3D-SDF for NP0034370 ((-)-7R-cannabicoumarononic acid A)

PDB for NP0034370 ((-)-7R-cannabicoumarononic acid A)

3D PDB for NP0034370 ((-)-7R-cannabicoumarononic acid A)

SMILES for NP0034370 ((-)-7R-cannabicoumarononic acid A)

INCHI for NP0034370 ((-)-7R-cannabicoumarononic acid A)

Structure for NP0034370 ((-)-7R-cannabicoumarononic acid A)

3D Structure for NP0034370 ((-)-7R-cannabicoumarononic acid A)