NP-MRD: Showing NP-Card for (+/-)-11-hydroxy-delta9-THC (NP0138952)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

1.0

Created at

2022-06-29 19:33:07 UTC

Updated at

2022-06-29 19:33:07 UTC

NP-MRD ID

NP0138952

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(+/-)-11-hydroxy-delta9-THC

Description

11-Hydroxy-Delta(9)-tetrahydrocannabinol, also known as 11-OH-THC, belongs to the class of organic compounds known as 2,2-dimethyl-1-benzopyrans. These are organic compounds containing a 1-benzopyran moiety that carries two methyl groups at the 2-position. 11-Hydroxy-Delta(9)-tetrahydrocannabinol is an extremely weak basic (essentially neutral) compound (based on its pKa). It was first documented in 2010 (PMID: 20630472). A phytocannabinoid that is Delta(9)-tetrahydrocannabinol in which the methyl group at C-11 has been hydroxylated (PMID: 21871147) (PMID: 24185550).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652303231705312D          

 26 28  0  0  1  0            999 V2000
   -4.2868    1.6500    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868    0.8250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.2868   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7158   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7158   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7158    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013    1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.0013    0.4125    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8138    1.9192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2835    2.8377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  4  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  2  9  1  0  0  0  0
  9 10  1  6  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
 11 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 17 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 24 26  2  0  0  0  0
  2 26  1  0  0  0  0
 15 26  1  0  0  0  0
M  END

     RDKit          3D

 54 56  0  0  0  0  0  0  0  0999 V2000
    6.2367    1.1841    0.3748 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4581   -0.2527    0.6605 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7764   -1.2651   -0.1670 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2937   -1.3352   -0.1397 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6379   -0.0943   -0.5949 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1411   -0.2127   -0.6116 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4477   -0.6364   -1.7042 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0672   -0.7403   -1.7025 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6001   -1.1705   -2.8271 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6378   -0.4209   -0.6041 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0590    0.0213    0.5390 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4220    0.1155    0.5134 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7373    0.3427    1.6527 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9416    1.0843    1.4850 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5949    2.5362    1.7339 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9203    0.6018    2.5035 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4845    0.9258    0.0537 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.9140    1.2707   -0.0286 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8454    0.2385   -0.5575 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2110   -0.7403   -1.4757 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0775   -1.3746   -2.5195 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1480   -2.0735   -1.9292 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9283   -1.0753   -1.3931 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0990   -0.4647   -0.3927 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.2489    1.6928    0.4809 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6204    1.7277    1.1491 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8608    1.4449   -0.6130 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5746   -0.4420    0.6775 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0930   -0.4079    1.7377 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1285   -1.1043   -1.2350 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2271   -2.2816    0.1032 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9020   -2.2583   -0.6412 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0243   -1.5397    0.9526 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8296    0.6920    0.1733 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0050    0.2952   -1.5561 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0025   -0.8968   -2.5939 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1573   -1.4252   -3.6768 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9571    0.4624    1.4158 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5594    2.7736    1.4003 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3269    3.2057    1.2449 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6289    2.7107    2.8349 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4471   -0.1011    3.2397 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7854    0.0573    2.0774 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2715    1.4680    3.1137 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8319    1.6371   -0.5395 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0018    2.1570   -0.7309 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3483    1.6617    0.9207 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3621   -0.3345    0.2662 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6957    0.7329   -1.1002 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4525   -0.6108   -3.2448 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5115   -2.1112   -3.1260 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7064   -2.7600   -1.3420 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5608   -1.8132   -2.0770 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2267   -1.0966    0.5533 H   0  0  0  0  0  0  0  0  0  0  0  0
 24 23  1  0
 23 20  2  0
 20 21  1  0
 21 22  1  0
 20 19  1  0
 19 18  1  0
 18 17  1  0
 17 14  1  0
 14 15  1  0
 14 16  1  0
 14 13  1  0
 13 11  1  0
 11 12  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
  7  8  1  0
  8  9  1  0
  8 10  2  0
 17 24  1  0
 10 11  1  0
 10 24  1  0
 24 54  1  1
 23 53  1  0
 21 50  1  0
 21 51  1  0
 22 52  1  0
 19 48  1  0
 19 49  1  0
 18 46  1  0
 18 47  1  0
 17 45  1  6
 15 39  1  0
 15 40  1  0
 15 41  1  0
 16 42  1  0
 16 43  1  0
 16 44  1  0
 12 38  1  0
  5 34  1  0
  5 35  1  0
  4 32  1  0
  4 33  1  0
  3 30  1  0
  3 31  1  0
  2 28  1  0
  2 29  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  7 36  1  0
  9 37  1  0
M  END


  Mrv1652303231705312D          

 26 28  0  0  1  0            999 V2000
   -4.2868    1.6500    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868    0.8250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.2868   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7158   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7158   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7158    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013    1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.0013    0.4125    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8138    1.9192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2835    2.8377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  4  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  2  9  1  0  0  0  0
  9 10  1  6  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
 11 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 17 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 24 26  2  0  0  0  0
  2 26  1  0  0  0  0
 15 26  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0138952

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@@]12C=C(CO)CC[C@@]1([H])C(C)(C)OC1=CC(CCCCC)=CC(O)=C21

> <INCHI_IDENTIFIER>
InChI=1S/C21H30O3/c1-4-5-6-7-14-11-18(23)20-16-10-15(13-22)8-9-17(16)21(2,3)24-19(20)12-14/h10-12,16-17,22-23H,4-9,13H2,1-3H3/t16-,17-/m1/s1

> <INCHI_KEY>
YCBKSSAWEUDACY-IAGOWNOFSA-N

> <FORMULA>
C21H30O3

> <MOLECULAR_WEIGHT>
330.468

> <EXACT_MASS>
330.219494826

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
54

> <JCHEM_AVERAGE_POLARIZABILITY>
39.923581367833876

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(6aR,10aR)-9-(hydroxymethyl)-6,6-dimethyl-3-pentyl-6H,6aH,7H,8H,10aH-benzo[c]isochromen-1-ol

> <ALOGPS_LOGP>
5.78

> <JCHEM_LOGP>
4.663385950666666

> <ALOGPS_LOGS>
-4.55

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.15741868828038

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.342413799705275

> <JCHEM_PKA_STRONGEST_BASIC>
-2.7299672945679365

> <JCHEM_POLAR_SURFACE_AREA>
49.69

> <JCHEM_REFRACTIVITY>
98.50819999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.34e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(6aR,10aR)-9-(hydroxymethyl)-6,6-dimethyl-3-pentyl-6aH,7H,8H,10aH-benzo[c]isochromen-1-ol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 23-MAR-17   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-MAR-17         0                                  
HETATM    1  H   UNK     0      -8.002   3.080   0.000  0.00  0.00           H+0
HETATM    2  C   UNK     0      -8.002   1.540   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -8.002  -0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -9.336  -0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -9.336  -2.310   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0     -10.669  -3.080   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0     -10.669  -0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0     -10.669   1.540   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -9.336   2.310   0.000  0.00  0.00           C+0
HETATM   10  H   UNK     0      -9.336   0.770   0.000  0.00  0.00           H+0
HETATM   11  C   UNK     0      -9.336   3.850   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0     -10.852   3.583   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -9.862   5.297   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      -8.002   4.620   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      -6.668   3.850   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -5.335   4.620   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -4.001   3.850   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -2.667   4.620   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -4.001   2.310   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -5.335   1.540   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      -5.335   0.000   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      -6.668   2.310   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    9   26                                             
CONECT    3    2    4                                                       
CONECT    4    3    5    7                                                  
CONECT    5    4    6                                                       
CONECT    6    5                                                            
CONECT    7    4    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8    2   10   11                                             
CONECT   10    9                                                            
CONECT   11    9   12   13   14                                             
CONECT   12   11                                                            
CONECT   13   11                                                            
CONECT   14   11   15                                                       
CONECT   15   14   16   26                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   23                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21                                                            
CONECT   23   17   24                                                       
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24    2   15                                                  
MASTER        0    0    0    0    0    0    0    0   26    0   56    0
END

View in JSmol

Synonyms

Value	Source
(-)-11-Hydroxy-Delta(9)-tetrahydrocannabinol	ChEBI
(-)-11-Hydroxy-Delta(9)-THC	ChEBI
(6AR,10ar)-6a,7,8,10a-tetrahydro-1-hydroxy-6,6-dimethyl-3-pentyl-6H-dibenzo[b,D]pyran-9-methanol	ChEBI
11-Hydroxytetrahydrocannabinol	ChEBI
11-OH-THC	ChEBI
(-)-11-Hydroxy-δ(9)-tetrahydrocannabinol	Generator
(-)-11-Hydroxy-δ(9)-THC	Generator
11-Hydroxy-δ(9)-tetrahydrocannabinol	Generator
11-Hydroxy-delta(9)-tetrahydrocannabinol, (6ar-trans)-isomer	HMDB
11-Hydroxy-delta(9)-tetrahydrocannabinol, (trans)-isomer	HMDB
11-Hydroxy-delta(9)-THC	HMDB
7-Hydroxy-delta(1)-tetrahydrocannabinol	HMDB

Chemical Formula

C₂₁H₃₀O₃

Average Mass

330.4680 Da

Monoisotopic Mass

330.21949 Da

IUPAC Name

(6aR,10aR)-9-(hydroxymethyl)-6,6-dimethyl-3-pentyl-6H,6aH,7H,8H,10aH-benzo[c]isochromen-1-ol

Traditional Name

(6aR,10aR)-9-(hydroxymethyl)-6,6-dimethyl-3-pentyl-6aH,7H,8H,10aH-benzo[c]isochromen-1-ol

CAS Registry Number

Not Available

SMILES

[H][C@@]12C=C(CO)CC[C@@]1([H])C(C)(C)OC1=CC(CCCCC)=CC(O)=C21

InChI Identifier

InChI=1S/C21H30O3/c1-4-5-6-7-14-11-18(23)20-16-10-15(13-22)8-9-17(16)21(2,3)24-19(20)12-14/h10-12,16-17,22-23H,4-9,13H2,1-3H3/t16-,17-/m1/s1

InChI Key

YCBKSSAWEUDACY-IAGOWNOFSA-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, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 2,2-dimethyl-1-benzopyrans. These are organic compounds containing a 1-benzopyran moiety that carries two methyl groups at the 2-position.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzopyrans

Sub Class

1-benzopyrans

Direct Parent

2,2-dimethyl-1-benzopyrans

Alternative Parents

Substituents

2,2-dimethyl-1-benzopyran
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Benzenoid
Oxacycle
Ether
Organic oxygen compound
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
Alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

phytocannabinoid (CHEBI:77270 )

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	5.78	ALOGPS
logP	4.66	ChemAxon
logS	-4.6	ALOGPS
pKa (Strongest Acidic)	9.34	ChemAxon
pKa (Strongest Basic)	-2.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	49.69 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	98.51 m³·mol⁻¹	ChemAxon
Polarizability	39.92 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	No	ChemAxon

External Links

HMDB ID

HMDB0062581

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

11-Hydroxy-THC

METLIN ID

Not Available

PubChem Compound

644022

PDB ID

Not Available

ChEBI ID

77270

Good Scents ID

Not Available

References

General References

Niemi MH, Turunen L, Pulli T, Nevanen TK, Hoyhtya M, Soderlund H, Rouvinen J, Takkinen K: A structural insight into the molecular recognition of a (-)-Delta9-tetrahydrocannabinol and the development of a sensitive, one-step, homogeneous immunocomplex-based assay for its detection. J Mol Biol. 2010 Jul 23;400(4):803-14. doi: 10.1016/j.jmb.2010.05.048. Epub 2010 May 26. [PubMed:20630472 ]
Lemos NP, Ingle EA: Cannabinoids in postmortem toxicology. J Anal Toxicol. 2011 Sep;35(7):394-401. doi: 10.1093/anatox/35.7.394. [PubMed:21871147 ]
Desrosiers NA, Lee D, Concheiro-Guisan M, Scheidweiler KB, Gorelick DA, Huestis MA: Urinary cannabinoid disposition in occasional and frequent smokers: is THC-glucuronide in sequential urine samples a marker of recent use in frequent smokers? Clin Chem. 2014 Feb;60(2):361-72. doi: 10.1373/clinchem.2013.214106. Epub 2013 Nov 1. [PubMed:24185550 ]

Showing NP-Card for (+/-)-11-hydroxy-delta9-THC (NP0138952)

MOL for NP0138952 ((+/-)-11-hydroxy-delta9-THC)

3D MOL for NP0138952 ((+/-)-11-hydroxy-delta9-THC)

3D SDF for NP0138952 ((+/-)-11-hydroxy-delta9-THC)

3D-SDF for NP0138952 ((+/-)-11-hydroxy-delta9-THC)

PDB for NP0138952 ((+/-)-11-hydroxy-delta9-THC)

3D PDB for NP0138952 ((+/-)-11-hydroxy-delta9-THC)

SMILES for NP0138952 ((+/-)-11-hydroxy-delta9-THC)

INCHI for NP0138952 ((+/-)-11-hydroxy-delta9-THC)

Structure for NP0138952 ((+/-)-11-hydroxy-delta9-THC)

3D Structure for NP0138952 ((+/-)-11-hydroxy-delta9-THC)