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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2017-03-23 04:31:18 UTC

Update Date

2022-03-07 03:17:56 UTC

HMDB ID

HMDB0062581

Secondary Accession Numbers

HMDB62581

Metabolite Identification

Common Name

11-hydroxy-Delta(9)-tetrahydrocannabinol

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). A phytocannabinoid that is Delta(9)-tetrahydrocannabinol in which the methyl group at C-11 has been hydroxylated .

Structure

MOL 3D MOL SDF 3D SDF PDB 3D 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

HMDB0062581
     RDKit          3D
11-hydroxy-Delta(9)-tetrahydrocannabinol
 54 56  0  0  0  0  0  0  0  0999 V2000
    6.5078   -1.0617    0.2229 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2417   -0.9833   -1.2332 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3171    0.0586   -1.7156 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9030   -0.0235   -1.2903 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6752    0.0438    0.1732 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1809    0.0208    0.3841 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5772   -1.2029    0.5318 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1944   -1.3151    0.7320 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3137   -2.5897    0.8668 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5205   -0.1784    0.7746 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0698    1.0941    0.6256 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4143    1.1566    0.4334 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7559    2.2291    0.6811 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0852    2.2053    0.2017 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9572    2.7994    1.2844 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1401    3.1187   -1.0016 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4801    0.7852   -0.1406 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.9057    0.6371   -0.4954 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7402   -0.2075    0.4007 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0245   -1.3756    0.9472 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7983   -2.6349    1.1947 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3314   -3.0414   -0.0435 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7123   -1.3179    1.2181 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9757   -0.1076    0.9773 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.2498   -0.1138    0.7254 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0884   -1.9578    0.7409 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6487   -1.1798    0.3217 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8263   -2.0145   -1.5167 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2229   -0.8714   -1.8049 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3121    0.1286   -2.8481 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7356    1.0886   -1.4307 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4904   -1.0125   -1.6818 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2669    0.7520   -1.8223 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0916    0.9107    0.6854 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0954   -0.8760    0.6739 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1494   -2.1096    0.4978 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2472   -3.4136    0.8299 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9168    2.1185    0.3132 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4762    2.5909    2.2769 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9976    2.4833    1.2433 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9046    3.9069    1.1617 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1727    3.5141   -1.1819 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5289    4.0171   -0.7428 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6958    2.6755   -1.8982 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8465    0.5293   -1.0453 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4286    1.6384   -0.5623 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0242    0.2338   -1.5463 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2346    0.3826    1.2191 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6191   -0.5897   -0.1986 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1440   -3.4275    1.6143 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6268   -2.4867    1.8933 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5982   -3.3734   -0.6205 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2957   -2.2046    1.6268 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0886    0.5514    1.9157 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  8 10  2  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 14 16  1  0
 14 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 20 23  2  0
 23 24  1  0
 12  6  1  0
 24 17  1  0
 24 10  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  2 28  1  0
  2 29  1  0
  3 30  1  0
  3 31  1  0
  4 32  1  0
  4 33  1  0
  5 34  1  0
  5 35  1  0
  7 36  1  0
  9 37  1  0
 12 38  1  0
 15 39  1  0
 15 40  1  0
 15 41  1  0
 16 42  1  0
 16 43  1  0
 16 44  1  0
 17 45  1  6
 18 46  1  0
 18 47  1  0
 19 48  1  0
 19 49  1  0
 21 50  1  0
 21 51  1  0
 22 52  1  0
 23 53  1  0
 24 54  1  1
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>
HMDB0062581

> <DATABASE_NAME>
hmdb

> <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

$$$$

HMDB0062581
     RDKit          3D
11-hydroxy-Delta(9)-tetrahydrocannabinol
 54 56  0  0  0  0  0  0  0  0999 V2000
    6.5078   -1.0617    0.2229 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2417   -0.9833   -1.2332 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3171    0.0586   -1.7156 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9030   -0.0235   -1.2903 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6752    0.0438    0.1732 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1809    0.0208    0.3841 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5772   -1.2029    0.5318 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1944   -1.3151    0.7320 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3137   -2.5897    0.8668 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5205   -0.1784    0.7746 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0698    1.0941    0.6256 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4143    1.1566    0.4334 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7559    2.2291    0.6811 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0852    2.2053    0.2017 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9572    2.7994    1.2844 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1401    3.1187   -1.0016 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4801    0.7852   -0.1406 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.9057    0.6371   -0.4954 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7402   -0.2075    0.4007 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0245   -1.3756    0.9472 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7983   -2.6349    1.1947 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3314   -3.0414   -0.0435 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7123   -1.3179    1.2181 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9757   -0.1076    0.9773 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.2498   -0.1138    0.7254 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0884   -1.9578    0.7409 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6487   -1.1798    0.3217 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8263   -2.0145   -1.5167 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2229   -0.8714   -1.8049 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3121    0.1286   -2.8481 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7356    1.0886   -1.4307 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4904   -1.0125   -1.6818 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2669    0.7520   -1.8223 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0916    0.9107    0.6854 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0954   -0.8760    0.6739 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1494   -2.1096    0.4978 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2472   -3.4136    0.8299 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9168    2.1185    0.3132 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4762    2.5909    2.2769 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9976    2.4833    1.2433 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9046    3.9069    1.1617 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1727    3.5141   -1.1819 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5289    4.0171   -0.7428 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6958    2.6755   -1.8982 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8465    0.5293   -1.0453 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4286    1.6384   -0.5623 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0242    0.2338   -1.5463 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2346    0.3826    1.2191 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6191   -0.5897   -0.1986 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1440   -3.4275    1.6143 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6268   -2.4867    1.8933 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5982   -3.3734   -0.6205 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2957   -2.2046    1.6268 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0886    0.5514    1.9157 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  8 10  2  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 14 16  1  0
 14 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 20 23  2  0
 23 24  1  0
 12  6  1  0
 24 17  1  0
 24 10  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  2 28  1  0
  2 29  1  0
  3 30  1  0
  3 31  1  0
  4 32  1  0
  4 33  1  0
  5 34  1  0
  5 35  1  0
  7 36  1  0
  9 37  1  0
 12 38  1  0
 15 39  1  0
 15 40  1  0
 15 41  1  0
 16 42  1  0
 16 43  1  0
 16 44  1  0
 17 45  1  6
 18 46  1  0
 18 47  1  0
 19 48  1  0
 19 49  1  0
 21 50  1  0
 21 51  1  0
 22 52  1  0
 23 53  1  0
 24 54  1  1
M  END

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

COMPND    HMDB0062581
HETATM    1  C1  UNL     1       6.508  -1.062   0.223  1.00  0.00           C  
HETATM    2  C2  UNL     1       6.242  -0.983  -1.233  1.00  0.00           C  
HETATM    3  C3  UNL     1       5.317   0.059  -1.716  1.00  0.00           C  
HETATM    4  C4  UNL     1       3.903  -0.023  -1.290  1.00  0.00           C  
HETATM    5  C5  UNL     1       3.675   0.044   0.173  1.00  0.00           C  
HETATM    6  C6  UNL     1       2.181   0.021   0.384  1.00  0.00           C  
HETATM    7  C7  UNL     1       1.577  -1.203   0.532  1.00  0.00           C  
HETATM    8  C8  UNL     1       0.194  -1.315   0.732  1.00  0.00           C  
HETATM    9  O1  UNL     1      -0.314  -2.590   0.867  1.00  0.00           O  
HETATM   10  C9  UNL     1      -0.520  -0.178   0.775  1.00  0.00           C  
HETATM   11  C10 UNL     1       0.070   1.094   0.626  1.00  0.00           C  
HETATM   12  C11 UNL     1       1.414   1.157   0.433  1.00  0.00           C  
HETATM   13  O2  UNL     1      -0.756   2.229   0.681  1.00  0.00           O  
HETATM   14  C12 UNL     1      -2.085   2.205   0.202  1.00  0.00           C  
HETATM   15  C13 UNL     1      -2.957   2.799   1.284  1.00  0.00           C  
HETATM   16  C14 UNL     1      -2.140   3.119  -1.002  1.00  0.00           C  
HETATM   17  C15 UNL     1      -2.480   0.785  -0.141  1.00  0.00           C  
HETATM   18  C16 UNL     1      -3.906   0.637  -0.495  1.00  0.00           C  
HETATM   19  C17 UNL     1      -4.740  -0.208   0.401  1.00  0.00           C  
HETATM   20  C18 UNL     1      -4.024  -1.376   0.947  1.00  0.00           C  
HETATM   21  C19 UNL     1      -4.798  -2.635   1.195  1.00  0.00           C  
HETATM   22  O3  UNL     1      -5.331  -3.041  -0.043  1.00  0.00           O  
HETATM   23  C20 UNL     1      -2.712  -1.318   1.218  1.00  0.00           C  
HETATM   24  C21 UNL     1      -1.976  -0.108   0.977  1.00  0.00           C  
HETATM   25  H1  UNL     1       6.250  -0.114   0.725  1.00  0.00           H  
HETATM   26  H2  UNL     1       6.088  -1.958   0.741  1.00  0.00           H  
HETATM   27  H3  UNL     1       7.649  -1.180   0.322  1.00  0.00           H  
HETATM   28  H4  UNL     1       5.826  -2.014  -1.517  1.00  0.00           H  
HETATM   29  H5  UNL     1       7.223  -0.871  -1.805  1.00  0.00           H  
HETATM   30  H6  UNL     1       5.312   0.129  -2.848  1.00  0.00           H  
HETATM   31  H7  UNL     1       5.736   1.089  -1.431  1.00  0.00           H  
HETATM   32  H8  UNL     1       3.490  -1.013  -1.682  1.00  0.00           H  
HETATM   33  H9  UNL     1       3.267   0.752  -1.822  1.00  0.00           H  
HETATM   34  H10 UNL     1       4.092   0.911   0.685  1.00  0.00           H  
HETATM   35  H11 UNL     1       4.095  -0.876   0.674  1.00  0.00           H  
HETATM   36  H12 UNL     1       2.149  -2.110   0.498  1.00  0.00           H  
HETATM   37  H13 UNL     1       0.247  -3.414   0.830  1.00  0.00           H  
HETATM   38  H14 UNL     1       1.917   2.119   0.313  1.00  0.00           H  
HETATM   39  H15 UNL     1      -2.476   2.591   2.277  1.00  0.00           H  
HETATM   40  H16 UNL     1      -3.998   2.483   1.243  1.00  0.00           H  
HETATM   41  H17 UNL     1      -2.905   3.907   1.162  1.00  0.00           H  
HETATM   42  H18 UNL     1      -3.173   3.514  -1.182  1.00  0.00           H  
HETATM   43  H19 UNL     1      -1.529   4.017  -0.743  1.00  0.00           H  
HETATM   44  H20 UNL     1      -1.696   2.676  -1.898  1.00  0.00           H  
HETATM   45  H21 UNL     1      -1.846   0.529  -1.045  1.00  0.00           H  
HETATM   46  H22 UNL     1      -4.429   1.638  -0.562  1.00  0.00           H  
HETATM   47  H23 UNL     1      -4.024   0.234  -1.546  1.00  0.00           H  
HETATM   48  H24 UNL     1      -5.235   0.383   1.219  1.00  0.00           H  
HETATM   49  H25 UNL     1      -5.619  -0.590  -0.199  1.00  0.00           H  
HETATM   50  H26 UNL     1      -4.144  -3.427   1.614  1.00  0.00           H  
HETATM   51  H27 UNL     1      -5.627  -2.487   1.893  1.00  0.00           H  
HETATM   52  H28 UNL     1      -4.598  -3.373  -0.621  1.00  0.00           H  
HETATM   53  H29 UNL     1      -2.296  -2.205   1.627  1.00  0.00           H  
HETATM   54  H30 UNL     1      -2.089   0.551   1.916  1.00  0.00           H  
CONECT    1    2   25   26   27
CONECT    2    3   28   29
CONECT    3    4   30   31
CONECT    4    5   32   33
CONECT    5    6   34   35
CONECT    6    7    7   12
CONECT    7    8   36
CONECT    8    9   10   10
CONECT    9   37
CONECT   10   11   24
CONECT   11   12   12   13
CONECT   12   38
CONECT   13   14
CONECT   14   15   16   17
CONECT   15   39   40   41
CONECT   16   42   43   44
CONECT   17   18   24   45
CONECT   18   19   46   47
CONECT   19   20   48   49
CONECT   20   21   23   23
CONECT   21   22   50   51
CONECT   22   52
CONECT   23   24   53
CONECT   24   54
END

HMDB0062581
     RDKit          3D
11-hydroxy-Delta(9)-tetrahydrocannabinol
 54 56  0  0  0  0  0  0  0  0999 V2000
    6.5078   -1.0617    0.2229 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2417   -0.9833   -1.2332 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3171    0.0586   -1.7156 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9030   -0.0235   -1.2903 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6752    0.0438    0.1732 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1809    0.0208    0.3841 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5772   -1.2029    0.5318 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1944   -1.3151    0.7320 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3137   -2.5897    0.8668 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5205   -0.1784    0.7746 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0698    1.0941    0.6256 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4143    1.1566    0.4334 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7559    2.2291    0.6811 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0852    2.2053    0.2017 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9572    2.7994    1.2844 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1401    3.1187   -1.0016 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4801    0.7852   -0.1406 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.9057    0.6371   -0.4954 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7402   -0.2075    0.4007 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0245   -1.3756    0.9472 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7983   -2.6349    1.1947 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3314   -3.0414   -0.0435 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7123   -1.3179    1.2181 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9757   -0.1076    0.9773 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.2498   -0.1138    0.7254 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0884   -1.9578    0.7409 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6487   -1.1798    0.3217 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8263   -2.0145   -1.5167 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2229   -0.8714   -1.8049 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3121    0.1286   -2.8481 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7356    1.0886   -1.4307 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4904   -1.0125   -1.6818 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2669    0.7520   -1.8223 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0916    0.9107    0.6854 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0954   -0.8760    0.6739 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1494   -2.1096    0.4978 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2472   -3.4136    0.8299 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9168    2.1185    0.3132 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4762    2.5909    2.2769 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9976    2.4833    1.2433 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9046    3.9069    1.1617 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1727    3.5141   -1.1819 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5289    4.0171   -0.7428 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6958    2.6755   -1.8982 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8465    0.5293   -1.0453 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4286    1.6384   -0.5623 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0242    0.2338   -1.5463 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2346    0.3826    1.2191 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6191   -0.5897   -0.1986 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1440   -3.4275    1.6143 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6268   -2.4867    1.8933 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5982   -3.3734   -0.6205 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2957   -2.2046    1.6268 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0886    0.5514    1.9157 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  8 10  2  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 14 16  1  0
 14 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 20 23  2  0
 23 24  1  0
 12  6  1  0
 24 17  1  0
 24 10  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  2 28  1  0
  2 29  1  0
  3 30  1  0
  3 31  1  0
  4 32  1  0
  4 33  1  0
  5 34  1  0
  5 35  1  0
  7 36  1  0
  9 37  1  0
 12 38  1  0
 15 39  1  0
 15 40  1  0
 15 41  1  0
 16 42  1  0
 16 43  1  0
 16 44  1  0
 17 45  1  6
 18 46  1  0
 18 47  1  0
 19 48  1  0
 19 49  1  0
 21 50  1  0
 21 51  1  0
 22 52  1  0
 23 53  1  0
 24 54  1  1
M  END

View in JSmol View Stereo Labels

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 Molecular Weight

330.468

Monoisotopic Molecular Weight

330.219494826

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

36557-05-8

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

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 )

Ontology

Not Available

Exogenous (HMDB: HMDB0062581)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.0093 g/l	ALOGPS
LogP	5.78	ALOGPS

Experimental Chromatographic Properties

Not Available

Predicted Molecular 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

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	181.805	31661259
DarkChem	[M-H]-	177.912	31661259
DeepCCS	[M-2H]-	218.221	30932474
DeepCCS	[M+Na]+	193.677	30932474
AllCCS	[M+H]+	183.5	32859911
AllCCS	[M+H-H2O]+	180.5	32859911
AllCCS	[M+NH4]+	186.3	32859911
AllCCS	[M+Na]+	187.0	32859911
AllCCS	[M-H]-	189.2	32859911
AllCCS	[M+Na-2H]-	189.8	32859911
AllCCS	[M+HCOO]-	190.7	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	8.47 minutes	32390414
Predicted by Siyang on May 30, 2022	18.9527 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.09 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2755.0 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	488.6 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	228.6 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	225.6 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	438.3 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	1015.2 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	902.6 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	86.0 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1705.5 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	604.4 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1760.5 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	627.7 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	492.6 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	367.0 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	392.0 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	8.2 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
11-hydroxy-Delta(9)-tetrahydrocannabinol	[H][C@@]12C=C(CO)CC[C@@]1([H])C(C)(C)OC1=CC(CCCCC)=CC(O)=C21	3721.4	Standard polar	33892256
11-hydroxy-Delta(9)-tetrahydrocannabinol	[H][C@@]12C=C(CO)CC[C@@]1([H])C(C)(C)OC1=CC(CCCCC)=CC(O)=C21	2804.2	Standard non polar	33892256
11-hydroxy-Delta(9)-tetrahydrocannabinol	[H][C@@]12C=C(CO)CC[C@@]1([H])C(C)(C)OC1=CC(CCCCC)=CC(O)=C21	2902.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
11-hydroxy-Delta(9)-tetrahydrocannabinol,1TMS,isomer #1	CCCCCC1=CC(O)=C2C(=C1)OC(C)(C)[C@@H]1CCC(CO[Si](C)(C)C)=C[C@@H]21	2540.9	Semi standard non polar	33892256
11-hydroxy-Delta(9)-tetrahydrocannabinol,1TMS,isomer #2	CCCCCC1=CC2=C(C(O[Si](C)(C)C)=C1)[C@@H]1C=C(CO)CC[C@H]1C(C)(C)O2	2561.0	Semi standard non polar	33892256
11-hydroxy-Delta(9)-tetrahydrocannabinol,2TMS,isomer #1	CCCCCC1=CC2=C(C(O[Si](C)(C)C)=C1)[C@@H]1C=C(CO[Si](C)(C)C)CC[C@H]1C(C)(C)O2	2581.3	Semi standard non polar	33892256
11-hydroxy-Delta(9)-tetrahydrocannabinol,1TBDMS,isomer #1	CCCCCC1=CC(O)=C2C(=C1)OC(C)(C)[C@@H]1CCC(CO[Si](C)(C)C(C)(C)C)=C[C@@H]21	2782.9	Semi standard non polar	33892256
11-hydroxy-Delta(9)-tetrahydrocannabinol,1TBDMS,isomer #2	CCCCCC1=CC2=C(C(O[Si](C)(C)C(C)(C)C)=C1)[C@@H]1C=C(CO)CC[C@H]1C(C)(C)O2	2788.8	Semi standard non polar	33892256
11-hydroxy-Delta(9)-tetrahydrocannabinol,2TBDMS,isomer #1	CCCCCC1=CC2=C(C(O[Si](C)(C)C(C)(C)C)=C1)[C@@H]1C=C(CO[Si](C)(C)C(C)(C)C)CC[C@H]1C(C)(C)O2	3006.0	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 11-hydroxy-Delta(9)-tetrahydrocannabinol GC-MS (Non-derivatized) - 70eV, Positive	splash10-0q2j-3094000000-d72f2aa02202e5e7cee8	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 11-hydroxy-Delta(9)-tetrahydrocannabinol GC-MS (2 TMS) - 70eV, Positive	splash10-05ur-5405900000-79bd0cd65b75242f9905	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 11-hydroxy-Delta(9)-tetrahydrocannabinol GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 11-hydroxy-Delta(9)-tetrahydrocannabinol 10V, Positive-QTOF	splash10-01q9-0229000000-5b2b7fb128289cd4eb0f	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 11-hydroxy-Delta(9)-tetrahydrocannabinol 20V, Positive-QTOF	splash10-0229-3393000000-45adc3372058b0168f6d	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 11-hydroxy-Delta(9)-tetrahydrocannabinol 40V, Positive-QTOF	splash10-1073-9240000000-d3775dacb2ad8c9b7f6f	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 11-hydroxy-Delta(9)-tetrahydrocannabinol 10V, Negative-QTOF	splash10-004i-0019000000-0f31ad0b33a131cc92c6	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 11-hydroxy-Delta(9)-tetrahydrocannabinol 20V, Negative-QTOF	splash10-004j-0359000000-21d14b56c1f7aba53cd9	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 11-hydroxy-Delta(9)-tetrahydrocannabinol 40V, Negative-QTOF	splash10-03g0-0951000000-e084c8b8e35156da2fa1	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 11-hydroxy-Delta(9)-tetrahydrocannabinol 10V, Positive-QTOF	splash10-001i-0009000000-1c9347e11fa941f38c14	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 11-hydroxy-Delta(9)-tetrahydrocannabinol 20V, Positive-QTOF	splash10-03e9-1459000000-41e2691cbaab82a4cf4e	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 11-hydroxy-Delta(9)-tetrahydrocannabinol 40V, Positive-QTOF	splash10-0006-9830000000-cd735dd73094b4659853	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 11-hydroxy-Delta(9)-tetrahydrocannabinol 10V, Negative-QTOF	splash10-004i-0009000000-3acdbd949ad93c49c37e	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 11-hydroxy-Delta(9)-tetrahydrocannabinol 20V, Negative-QTOF	splash10-03fr-0009000000-0becf9a3490213d6fec3	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 11-hydroxy-Delta(9)-tetrahydrocannabinol 40V, Negative-QTOF	splash10-0571-0192000000-2527184cc89ea0159348	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB 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

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Showing metabocard for 11-hydroxy-Delta(9)-tetrahydrocannabinol (HMDB0062581)

MOL for HMDB0062581 (11-hydroxy-Delta(9)-tetrahydrocannabinol)

3D MOL for HMDB0062581 (11-hydroxy-Delta(9)-tetrahydrocannabinol)

3D SDF for HMDB0062581 (11-hydroxy-Delta(9)-tetrahydrocannabinol)

3D-SDF for HMDB0062581 (11-hydroxy-Delta(9)-tetrahydrocannabinol)

PDB for HMDB0062581 (11-hydroxy-Delta(9)-tetrahydrocannabinol)

3D PDB for HMDB0062581 (11-hydroxy-Delta(9)-tetrahydrocannabinol)

SMILES for HMDB0062581 (11-hydroxy-Delta(9)-tetrahydrocannabinol)

INCHI for HMDB0062581 (11-hydroxy-Delta(9)-tetrahydrocannabinol)

Structure for HMDB0062581 (11-hydroxy-Delta(9)-tetrahydrocannabinol)

3D Structure for HMDB0062581 (11-hydroxy-Delta(9)-tetrahydrocannabinol)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra