Record Information |
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Version | 5.0 |
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Status | Expected but not Quantified |
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Creation Date | 2017-03-23 04:31:18 UTC |
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Update Date | 2022-03-07 03:17:56 UTC |
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HMDB ID | HMDB0062581 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | 11-hydroxy-Delta(9)-tetrahydrocannabinol |
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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 . |
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Structure | [H][C@@]12C=C(CO)CC[C@@]1([H])C(C)(C)OC1=CC(CCCCC)=CC(O)=C21 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 |
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Synonyms | Value | Source |
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(-)-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 |
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Chemical Formula | C21H30O3 |
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Average Molecular Weight | 330.468 |
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Monoisotopic Molecular Weight | 330.219494826 |
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IUPAC Name | (6aR,10aR)-9-(hydroxymethyl)-6,6-dimethyl-3-pentyl-6H,6aH,7H,8H,10aH-benzo[c]isochromen-1-ol |
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Traditional Name | (6aR,10aR)-9-(hydroxymethyl)-6,6-dimethyl-3-pentyl-6aH,7H,8H,10aH-benzo[c]isochromen-1-ol |
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CAS Registry Number | 36557-05-8 |
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SMILES | [H][C@@]12C=C(CO)CC[C@@]1([H])C(C)(C)OC1=CC(CCCCC)=CC(O)=C21 |
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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 |
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InChI Key | YCBKSSAWEUDACY-IAGOWNOFSA-N |
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Chemical Taxonomy |
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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. |
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Kingdom | Organic compounds |
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Super Class | Organoheterocyclic compounds |
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Class | Benzopyrans |
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Sub Class | 1-benzopyrans |
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Direct Parent | 2,2-dimethyl-1-benzopyrans |
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Alternative Parents | |
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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
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Molecular Framework | Aromatic heteropolycyclic compounds |
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External Descriptors | |
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Ontology |
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Physiological effect | Not Available |
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Disposition | |
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Process | Not Available |
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Role | Not Available |
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Physical Properties |
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State | Not Available |
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Experimental Molecular Properties | Property | Value | Reference |
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Melting Point | Not Available | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | 0.0093 g/l | ALOGPS | LogP | 5.78 | ALOGPS |
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Experimental Chromatographic Properties | Not Available |
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Predicted Molecular Properties | |
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Predicted Chromatographic Properties | Predicted Collision Cross SectionsPredicted Kovats Retention IndicesUnderivatizedDerivatizedDerivative Name / Structure | SMILES | Kovats RI Value | Column Type | Reference |
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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 |
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| GC-MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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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 SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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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 |
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