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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-10 21:31:17 UTC

Update Date

2021-09-26 22:52:02 UTC

HMDB ID

HMDB0244358

Secondary Accession Numbers

None

Metabolite Identification

Common Name

11-Hydroxy-delta(8)-thc

Description

9-(hydroxymethyl)-6,6-dimethyl-3-pentyl-6H,6aH,7H,10H,10aH-benzo[c]isochromen-1-ol 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. Based on a literature review very few articles have been published on 9-(hydroxymethyl)-6,6-dimethyl-3-pentyl-6H,6aH,7H,10H,10aH-benzo[c]isochromen-1-ol. This compound has been identified in human blood as reported by (PMID: 31557052 ). 11-hydroxy-delta(8)-thc is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically 11-Hydroxy-delta(8)-thc is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HMDB0244358
     RDKit          3D
11-Hydroxy-delta(8)-thc
 54 56  0  0  0  0  0  0  0  0999 V2000
    6.3705   -0.1583    1.2401 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3058   -1.2299    0.2058 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4104   -1.0207   -0.9469 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9725   -0.9269   -0.6714 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5801    0.1856    0.2254 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0661    0.1427    0.3269 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4492   -0.5960    1.2891 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0566   -0.6483    1.3986 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5218   -1.4170    2.3981 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7003    0.0623    0.5143 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0941    0.8101   -0.4589 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3018    0.8585   -0.5638 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9215    1.5039   -1.3187 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0957    2.1100   -0.8188 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6584    3.3456   -0.0379 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8873    2.6411   -1.9971 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9053    1.1694    0.0282 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1972    0.8006   -0.6887 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7946   -0.4682   -0.2034 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0487   -1.5112    0.1356 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5482   -2.8096    0.6263 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9189   -2.8715    0.7147 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5798   -1.3160   -0.0013 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1668    0.0216    0.5992 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4662    0.0259    1.4953 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9319   -0.4497    2.2202 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0119    0.8167    0.9092 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3562   -1.3664   -0.2114 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0260   -2.2126    0.7094 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7162   -0.0765   -1.4920 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5408   -1.8893   -1.6818 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5499   -1.8869   -0.2403 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4087   -0.8133   -1.6379 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8842    0.0269    1.3032 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8725    1.1895   -0.0905 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0660   -1.1577    1.9876 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0030   -1.9467    3.0585 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7658    1.4497   -1.3333 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0921    3.9712   -0.7620 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9648    3.0994    0.7809 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5261    3.9564    0.2875 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9322    2.8383   -1.7796 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8065    1.9436   -2.8542 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4543    3.6214   -2.3547 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2579    1.7998    0.9032 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9822    0.6580   -1.7889 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9638    1.5917   -0.5427 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8690   -0.5833   -0.1102 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2326   -3.5869   -0.1302 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0314   -3.0594    1.5750 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2831   -3.1382   -0.1492 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2424   -1.3124   -1.0414 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0405   -2.0883    0.5838 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3950   -0.0985    1.7052 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  2  0
 20 21  1  0
 21 22  1  0
 20 23  1  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  0
 18 46  1  0
 18 47  1  0
 19 48  1  0
 21 49  1  0
 21 50  1  0
 22 51  1  0
 23 52  1  0
 23 53  1  0
 24 54  1  0
M  END


  Mrv1652309102123312D          

 24 26  0  0  0  0            999 V2000
   -1.4289   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -2.4750    0.0000 C   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
    5.7158   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8258   -4.5663    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4385   -5.2371    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   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 10 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
  8 17  1  0  0  0  0
 16 18  1  0  0  0  0
 16 19  1  0  0  0  0
 12 20  1  0  0  0  0
 20 21  1  0  0  0  0
  9 22  1  0  0  0  0
 22 23  2  0  0  0  0
  6 23  1  0  0  0  0
 22 24  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0244358

> <DATABASE_NAME>
hmdb

> <SMILES>
CCCCCC1=CC2=C(C3CC(CO)=CCC3C(C)(C)O2)C(O)=C1

> <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/h8,11-12,16-17,22-23H,4-7,9-10,13H2,1-3H3

> <INCHI_KEY>
LOUSQMWLMDHRIK-UHFFFAOYSA-N

> <FORMULA>
C21H30O3

> <MOLECULAR_WEIGHT>
330.468

> <EXACT_MASS>
330.219494826

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
54

> <JCHEM_AVERAGE_POLARIZABILITY>
39.54984668434465

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
5.96

> <JCHEM_LOGP>
4.663385950666666

> <ALOGPS_LOGS>
-4.59

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.160106886816923

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.027598052745365

> <JCHEM_PKA_STRONGEST_BASIC>
-2.7287714683784436

> <JCHEM_POLAR_SURFACE_AREA>
49.69

> <JCHEM_REFRACTIVITY>
98.5082

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.51e-03 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0244358
     RDKit          3D
11-Hydroxy-delta(8)-thc
 54 56  0  0  0  0  0  0  0  0999 V2000
    6.3705   -0.1583    1.2401 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3058   -1.2299    0.2058 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4104   -1.0207   -0.9469 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9725   -0.9269   -0.6714 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5801    0.1856    0.2254 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0661    0.1427    0.3269 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4492   -0.5960    1.2891 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0566   -0.6483    1.3986 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5218   -1.4170    2.3981 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7003    0.0623    0.5143 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0941    0.8101   -0.4589 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3018    0.8585   -0.5638 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9215    1.5039   -1.3187 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0957    2.1100   -0.8188 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6584    3.3456   -0.0379 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8873    2.6411   -1.9971 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9053    1.1694    0.0282 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1972    0.8006   -0.6887 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7946   -0.4682   -0.2034 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0487   -1.5112    0.1356 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5482   -2.8096    0.6263 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9189   -2.8715    0.7147 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5798   -1.3160   -0.0013 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1668    0.0216    0.5992 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4662    0.0259    1.4953 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9319   -0.4497    2.2202 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0119    0.8167    0.9092 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3562   -1.3664   -0.2114 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0260   -2.2126    0.7094 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7162   -0.0765   -1.4920 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5408   -1.8893   -1.6818 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5499   -1.8869   -0.2403 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4087   -0.8133   -1.6379 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8842    0.0269    1.3032 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8725    1.1895   -0.0905 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0660   -1.1577    1.9876 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0030   -1.9467    3.0585 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7658    1.4497   -1.3333 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0921    3.9712   -0.7620 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9648    3.0994    0.7809 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5261    3.9564    0.2875 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9322    2.8383   -1.7796 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8065    1.9436   -2.8542 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4543    3.6214   -2.3547 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2579    1.7998    0.9032 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9822    0.6580   -1.7889 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9638    1.5917   -0.5427 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8690   -0.5833   -0.1102 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2326   -3.5869   -0.1302 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0314   -3.0594    1.5750 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2831   -3.1382   -0.1492 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2424   -1.3124   -1.0414 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0405   -2.0883    0.5838 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3950   -0.0985    1.7052 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  2  0
 20 21  1  0
 21 22  1  0
 20 23  1  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  0
 18 46  1  0
 18 47  1  0
 19 48  1  0
 21 49  1  0
 21 50  1  0
 22 51  1  0
 23 52  1  0
 23 53  1  0
 24 54  1  0
M  END

HEADER    PROTEIN                                 10-SEP-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-SEP-21         0                                  
HETATM    1  C   UNK     0      -2.667  -9.240   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.334  -8.470   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000  -9.240   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334  -8.470   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667  -9.240   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.001  -8.470   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.335  -9.240   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.668  -8.470   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.668  -6.930   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.002  -6.160   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.002  -4.620   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       9.336  -3.850   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      10.669  -4.620   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      10.669  -6.160   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       9.336  -6.930   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       9.336  -8.470   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       8.002  -9.240   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      10.875  -8.524   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      10.152  -9.776   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       9.336  -2.310   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      10.669  -1.540   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       5.335  -6.160   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       5.335  -4.620   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   23                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   17                                                  
CONECT    9    8   10   22                                                  
CONECT   10    9   11   15                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   20                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   10   16                                                  
CONECT   16   15   17   18   19                                             
CONECT   17   16    8                                                       
CONECT   18   16                                                            
CONECT   19   16                                                            
CONECT   20   12   21                                                       
CONECT   21   20                                                            
CONECT   22    9   23   24                                                  
CONECT   23   22    6                                                       
CONECT   24   22                                                            
MASTER        0    0    0    0    0    0    0    0   24    0   52    0
END

COMPND    HMDB0244358
HETATM    1  C1  UNL     1       6.370  -0.158   1.240  1.00  0.00           C  
HETATM    2  C2  UNL     1       6.306  -1.230   0.206  1.00  0.00           C  
HETATM    3  C3  UNL     1       5.410  -1.021  -0.947  1.00  0.00           C  
HETATM    4  C4  UNL     1       3.973  -0.927  -0.671  1.00  0.00           C  
HETATM    5  C5  UNL     1       3.580   0.186   0.225  1.00  0.00           C  
HETATM    6  C6  UNL     1       2.066   0.143   0.327  1.00  0.00           C  
HETATM    7  C7  UNL     1       1.449  -0.596   1.289  1.00  0.00           C  
HETATM    8  C8  UNL     1       0.057  -0.648   1.399  1.00  0.00           C  
HETATM    9  O1  UNL     1      -0.522  -1.417   2.398  1.00  0.00           O  
HETATM   10  C9  UNL     1      -0.700   0.062   0.514  1.00  0.00           C  
HETATM   11  C10 UNL     1      -0.094   0.810  -0.459  1.00  0.00           C  
HETATM   12  C11 UNL     1       1.302   0.859  -0.564  1.00  0.00           C  
HETATM   13  O2  UNL     1      -0.921   1.504  -1.319  1.00  0.00           O  
HETATM   14  C12 UNL     1      -2.096   2.110  -0.819  1.00  0.00           C  
HETATM   15  C13 UNL     1      -1.658   3.346  -0.038  1.00  0.00           C  
HETATM   16  C14 UNL     1      -2.887   2.641  -1.997  1.00  0.00           C  
HETATM   17  C15 UNL     1      -2.905   1.169   0.028  1.00  0.00           C  
HETATM   18  C16 UNL     1      -4.197   0.801  -0.689  1.00  0.00           C  
HETATM   19  C17 UNL     1      -4.795  -0.468  -0.203  1.00  0.00           C  
HETATM   20  C18 UNL     1      -4.049  -1.511   0.136  1.00  0.00           C  
HETATM   21  C19 UNL     1      -4.548  -2.810   0.626  1.00  0.00           C  
HETATM   22  O3  UNL     1      -5.919  -2.872   0.715  1.00  0.00           O  
HETATM   23  C20 UNL     1      -2.580  -1.316  -0.001  1.00  0.00           C  
HETATM   24  C21 UNL     1      -2.167   0.022   0.599  1.00  0.00           C  
HETATM   25  H1  UNL     1       7.466   0.026   1.495  1.00  0.00           H  
HETATM   26  H2  UNL     1       5.932  -0.450   2.220  1.00  0.00           H  
HETATM   27  H3  UNL     1       6.012   0.817   0.909  1.00  0.00           H  
HETATM   28  H4  UNL     1       7.356  -1.366  -0.211  1.00  0.00           H  
HETATM   29  H5  UNL     1       6.026  -2.213   0.709  1.00  0.00           H  
HETATM   30  H6  UNL     1       5.716  -0.076  -1.492  1.00  0.00           H  
HETATM   31  H7  UNL     1       5.541  -1.889  -1.682  1.00  0.00           H  
HETATM   32  H8  UNL     1       3.550  -1.887  -0.240  1.00  0.00           H  
HETATM   33  H9  UNL     1       3.409  -0.813  -1.638  1.00  0.00           H  
HETATM   34  H10 UNL     1       3.884   0.027   1.303  1.00  0.00           H  
HETATM   35  H11 UNL     1       3.873   1.189  -0.091  1.00  0.00           H  
HETATM   36  H12 UNL     1       2.066  -1.158   1.988  1.00  0.00           H  
HETATM   37  H13 UNL     1       0.003  -1.947   3.059  1.00  0.00           H  
HETATM   38  H14 UNL     1       1.766   1.450  -1.333  1.00  0.00           H  
HETATM   39  H15 UNL     1      -1.092   3.971  -0.762  1.00  0.00           H  
HETATM   40  H16 UNL     1      -0.965   3.099   0.781  1.00  0.00           H  
HETATM   41  H17 UNL     1      -2.526   3.956   0.287  1.00  0.00           H  
HETATM   42  H18 UNL     1      -3.932   2.838  -1.780  1.00  0.00           H  
HETATM   43  H19 UNL     1      -2.807   1.944  -2.854  1.00  0.00           H  
HETATM   44  H20 UNL     1      -2.454   3.621  -2.355  1.00  0.00           H  
HETATM   45  H21 UNL     1      -3.258   1.800   0.903  1.00  0.00           H  
HETATM   46  H22 UNL     1      -3.982   0.658  -1.789  1.00  0.00           H  
HETATM   47  H23 UNL     1      -4.964   1.592  -0.543  1.00  0.00           H  
HETATM   48  H24 UNL     1      -5.869  -0.583  -0.110  1.00  0.00           H  
HETATM   49  H25 UNL     1      -4.233  -3.587  -0.130  1.00  0.00           H  
HETATM   50  H26 UNL     1      -4.031  -3.059   1.575  1.00  0.00           H  
HETATM   51  H27 UNL     1      -6.283  -3.138  -0.149  1.00  0.00           H  
HETATM   52  H28 UNL     1      -2.242  -1.312  -1.041  1.00  0.00           H  
HETATM   53  H29 UNL     1      -2.041  -2.088   0.584  1.00  0.00           H  
HETATM   54  H30 UNL     1      -2.395  -0.098   1.705  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   20   48
CONECT   20   21   23
CONECT   21   22   49   50
CONECT   22   51
CONECT   23   24   52   53
CONECT   24   54
END

HMDB0244358
     RDKit          3D
11-Hydroxy-delta(8)-thc
 54 56  0  0  0  0  0  0  0  0999 V2000
    6.3705   -0.1583    1.2401 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3058   -1.2299    0.2058 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4104   -1.0207   -0.9469 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9725   -0.9269   -0.6714 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5801    0.1856    0.2254 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0661    0.1427    0.3269 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4492   -0.5960    1.2891 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0566   -0.6483    1.3986 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5218   -1.4170    2.3981 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7003    0.0623    0.5143 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0941    0.8101   -0.4589 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3018    0.8585   -0.5638 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9215    1.5039   -1.3187 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0957    2.1100   -0.8188 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6584    3.3456   -0.0379 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8873    2.6411   -1.9971 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9053    1.1694    0.0282 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1972    0.8006   -0.6887 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7946   -0.4682   -0.2034 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0487   -1.5112    0.1356 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5482   -2.8096    0.6263 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9189   -2.8715    0.7147 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5798   -1.3160   -0.0013 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1668    0.0216    0.5992 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4662    0.0259    1.4953 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9319   -0.4497    2.2202 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0119    0.8167    0.9092 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3562   -1.3664   -0.2114 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0260   -2.2126    0.7094 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7162   -0.0765   -1.4920 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5408   -1.8893   -1.6818 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5499   -1.8869   -0.2403 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4087   -0.8133   -1.6379 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8842    0.0269    1.3032 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8725    1.1895   -0.0905 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0660   -1.1577    1.9876 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0030   -1.9467    3.0585 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7658    1.4497   -1.3333 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0921    3.9712   -0.7620 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9648    3.0994    0.7809 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5261    3.9564    0.2875 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9322    2.8383   -1.7796 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8065    1.9436   -2.8542 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4543    3.6214   -2.3547 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2579    1.7998    0.9032 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9822    0.6580   -1.7889 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9638    1.5917   -0.5427 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8690   -0.5833   -0.1102 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2326   -3.5869   -0.1302 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0314   -3.0594    1.5750 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2831   -3.1382   -0.1492 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2424   -1.3124   -1.0414 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0405   -2.0883    0.5838 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3950   -0.0985    1.7052 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  2  0
 20 21  1  0
 21 22  1  0
 20 23  1  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  0
 18 46  1  0
 18 47  1  0
 19 48  1  0
 21 49  1  0
 21 50  1  0
 22 51  1  0
 23 52  1  0
 23 53  1  0
 24 54  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
11-Hydroxy-δ(8)-THC	Generator
11-Hydroxy-delta(8)-tetrahydrocannabinol	MeSH
11-Hydroxy-delta(8)-tetrahydrocannabinol, (6ar-trans)-isomer	MeSH

Chemical Formula

C₂₁H₃₀O₃

Average Molecular Weight

330.468

Monoisotopic Molecular Weight

330.219494826

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

CCCCCC1=CC2=C(C3CC(CO)=CCC3C(C)(C)O2)C(O)=C1

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/h8,11-12,16-17,22-23H,4-7,9-10,13H2,1-3H3

InChI Key

LOUSQMWLMDHRIK-UHFFFAOYSA-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

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

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	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	5.96	ALOGPS
logP	4.66	ChemAxon
logS	-4.6	ALOGPS
pKa (Strongest Acidic)	10.03	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	39.55 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
DeepCCS	[M+H]+	198.915	30932474
DeepCCS	[M-H]-	196.365	30932474
DeepCCS	[M-2H]-	230.127	30932474
DeepCCS	[M+Na]+	206.293	30932474
AllCCS	[M+H]+	183.5	32859911
AllCCS	[M+H-H2O]+	180.5	32859911
AllCCS	[M+NH4]+	186.3	32859911
AllCCS	[M+Na]+	187.1	32859911
AllCCS	[M-H]-	189.2	32859911
AllCCS	[M+Na-2H]-	189.9	32859911
AllCCS	[M+HCOO]-	190.8	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
11-Hydroxy-delta(8)-thc	CCCCCC1=CC2=C(C3CC(CO)=CCC3C(C)(C)O2)C(O)=C1	3571.7	Standard polar	33892256
11-Hydroxy-delta(8)-thc	CCCCCC1=CC2=C(C3CC(CO)=CCC3C(C)(C)O2)C(O)=C1	2723.8	Standard non polar	33892256
11-Hydroxy-delta(8)-thc	CCCCCC1=CC2=C(C3CC(CO)=CCC3C(C)(C)O2)C(O)=C1	2898.5	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(8)-thc GC-MS (Non-derivatized) - 70eV, Positive	splash10-00xs-5094000000-2e57ccaf0e0f54f9f760	2021-09-24	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 11-Hydroxy-delta(8)-thc GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 11-Hydroxy-delta(8)-thc GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 11-Hydroxy-delta(8)-thc GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 11-Hydroxy-delta(8)-thc GC-MS (TMS_2_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 11-Hydroxy-delta(8)-thc GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 11-Hydroxy-delta(8)-thc GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 11-Hydroxy-delta(8)-thc GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	2021-11-03	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(8)-thc 10V, Positive-QTOF	splash10-001i-0009000000-c02b0dd42396d1c408db	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 11-Hydroxy-delta(8)-thc 20V, Positive-QTOF	splash10-001i-0129000000-24e86d7283c942221270	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 11-Hydroxy-delta(8)-thc 40V, Positive-QTOF	splash10-0v0d-9764000000-87b178505feec0078847	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 11-Hydroxy-delta(8)-thc 10V, Negative-QTOF	splash10-004i-0009000000-3acdbd949ad93c49c37e	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 11-Hydroxy-delta(8)-thc 20V, Negative-QTOF	splash10-004i-0009000000-43097c53ba50769df8c7	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 11-Hydroxy-delta(8)-thc 40V, Negative-QTOF	splash10-05r3-0092000000-a7f98665565b9cc0fb30	2021-10-12	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	31557052	details

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

30720

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

33252

PDB ID

Not Available

ChEBI ID

Not Available

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

Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]

Showing metabocard for 11-Hydroxy-delta(8)-thc (HMDB0244358)

MOL for HMDB0244358 (11-Hydroxy-delta(8)-thc)

3D MOL for HMDB0244358 (11-Hydroxy-delta(8)-thc)

3D SDF for HMDB0244358 (11-Hydroxy-delta(8)-thc)

3D-SDF for HMDB0244358 (11-Hydroxy-delta(8)-thc)

PDB for HMDB0244358 (11-Hydroxy-delta(8)-thc)

3D PDB for HMDB0244358 (11-Hydroxy-delta(8)-thc)

SMILES for HMDB0244358 (11-Hydroxy-delta(8)-thc)

INCHI for HMDB0244358 (11-Hydroxy-delta(8)-thc)

Structure for HMDB0244358 (11-Hydroxy-delta(8)-thc)

3D Structure for HMDB0244358 (11-Hydroxy-delta(8)-thc)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra