| Record Information |
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| Version | 2.0 |
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| Created at | 2021-06-20 20:47:14 UTC |
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| Updated at | 2021-06-30 00:10:31 UTC |
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| NP-MRD ID | NP0037985 |
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| Secondary Accession Numbers | None |
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| Natural Product Identification |
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| Common Name | 3,4-dihydro-6-hydroxy-10,11-epoxymanzamine A |
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| Provided By | JEOL Database |
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| Description | (4AR)-2,7-[(Z)-5-Octene-1,8-diyl]-5-(6-hydroxy-3,4-dihydro-9H-pyrido[3,4-b]indole-1-yl)-8alpha,8aalpha-[[(8R)-1,2,3,4,5,8-hexahydroazocine-1,8beta-diyl]methylene]-5beta,6beta-epoxy-1,2,3,4,4aalpha,5,6,7,8,8a-decahydroisoquinoline-7alpha-ol belongs to the class of organic compounds known as harmala alkaloids. Harmala alkaloids are compounds with a structure based on harmaline, harmine, harmalol, harman or a derivative of those parents. These parents are beta-carbolines, consisting of a pyrimidine fused to the pyrrole moiety of an indole to form a pyrido[3,4-b]indole. 3,4-dihydro-6-hydroxy-10,11-epoxymanzamine A is found in Amphimedon sp. 3,4-dihydro-6-hydroxy-10,11-epoxymanzamine A was first documented in 2009 (Yamada, M., et al.). Based on a literature review very few articles have been published on (4aR)-2,7-[(Z)-5-Octene-1,8-diyl]-5-(6-hydroxy-3,4-dihydro-9H-pyrido[3,4-b]indole-1-yl)-8alpha,8aalpha-[[(8R)-1,2,3,4,5,8-hexahydroazocine-1,8beta-diyl]methylene]-5beta,6beta-epoxy-1,2,3,4,4aalpha,5,6,7,8,8a-decahydroisoquinoline-7alpha-ol. |
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| Structure | [H]OC1=C([H])C2=C(N([H])C3=C2C([H])([H])C([H])([H])N=C3[C@]23O[C@@]2([H])[C@@]2(O[H])C([H])([H])C([H])([H])\C([H])=C([H])/C([H])([H])C([H])([H])C([H])([H])C([H])([H])[N@@]4C([H])([H])C([H])([H])[C@]3([H])[C@]3(C([H])([H])[C@]5([H])\C([H])=C([H])/C([H])([H])C([H])([H])C([H])([H])C([H])([H])N5[C@@]23[H])C4([H])[H])C([H])=C1[H] InChI=1S/C36H46N4O3/c41-25-12-13-28-27(21-25)26-14-17-37-31(30(26)38-28)36-29-15-20-39-18-9-5-2-1-4-8-16-35(42,33(36)43-36)32-34(29,23-39)22-24-11-7-3-6-10-19-40(24)32/h1,4,7,11-13,21,24,29,32-33,38,41-42H,2-3,5-6,8-10,14-20,22-23H2/b4-1-,11-7-/t24-,29+,32+,33-,34-,35+,36-/m0/s1 |
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| Synonyms | | Value | Source |
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| (4AR)-2,7-[(Z)-5-octene-1,8-diyl]-5-(6-hydroxy-3,4-dihydro-9H-pyrido[3,4-b]indole-1-yl)-8a,8aalpha-[[(8R)-1,2,3,4,5,8-hexahydroazocine-1,8b-diyl]methylene]-5b,6b-epoxy-1,2,3,4,4aalpha,5,6,7,8,8a-decahydroisoquinoline-7a-ol | Generator | | (4AR)-2,7-[(Z)-5-octene-1,8-diyl]-5-(6-hydroxy-3,4-dihydro-9H-pyrido[3,4-b]indole-1-yl)-8α,8aalpha-[[(8R)-1,2,3,4,5,8-hexahydroazocine-1,8β-diyl]methylene]-5β,6β-epoxy-1,2,3,4,4aalpha,5,6,7,8,8a-decahydroisoquinoline-7α-ol | Generator |
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| Chemical Formula | C36H46N4O3 |
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| Average Mass | 582.7890 Da |
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| Monoisotopic Mass | 582.35699 Da |
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| IUPAC Name | (1R,2R,4R,5Z,12R,13R,16Z,22R,25S,27S)-25-{6-hydroxy-3H,4H,9H-pyrido[3,4-b]indol-1-yl}-26-oxa-11,22-diazahexacyclo[11.11.3.1^{2,22}.0^{2,12}.0^{4,11}.0^{25,27}]octacosa-5,16-dien-13-ol |
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| Traditional Name | (1R,2R,4R,5Z,12R,13R,16Z,22R,25S,27S)-25-{6-hydroxy-3H,4H,9H-pyrido[3,4-b]indol-1-yl}-26-oxa-11,22-diazahexacyclo[11.11.3.1^{2,22}.0^{2,12}.0^{4,11}.0^{25,27}]octacosa-5,16-dien-13-ol |
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| CAS Registry Number | Not Available |
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| SMILES | [H]OC1=C([H])C2=C(N([H])C3=C2C([H])([H])C([H])([H])N=C3[C@]23O[C@@]2([H])[C@@]2(O[H])C([H])([H])C([H])([H])\C([H])=C([H])/C([H])([H])C([H])([H])C([H])([H])C([H])([H])[N@@]4C([H])([H])C([H])([H])[C@]3([H])[C@]3(C([H])([H])[C@]5([H])\C([H])=C([H])/C([H])([H])C([H])([H])C([H])([H])C([H])([H])N5[C@@]23[H])C4([H])[H])C([H])=C1[H] |
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| InChI Identifier | InChI=1S/C36H46N4O3/c41-25-12-13-28-27(21-25)26-14-17-37-31(30(26)38-28)36-29-15-20-39-18-9-5-2-1-4-8-16-35(42,33(36)43-36)32-34(29,23-39)22-24-11-7-3-6-10-19-40(24)32/h1,4,7,11-13,21,24,29,32-33,38,41-42H,2-3,5-6,8-10,14-20,22-23H2/b4-1-,11-7-/t24-,29+,32+,33-,34-,35+,36-/m0/s1 |
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| InChI Key | WUNUWEQIIMWSQX-WJXWIWBUSA-N |
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| Experimental Spectra |
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| | Spectrum Type | Description | Depositor Email | Depositor Organization | Depositor | Deposition Date | View |
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| 1D NMR | 13C NMR Spectrum (1D, 500 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 500 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 100 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 100 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 200 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 200 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 300 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 300 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 400 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 400 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 600 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 700 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 700 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 800 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 800 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 900 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 900 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 1000 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, CDCl3, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum |
| | Predicted Spectra |
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| Not Available | | Chemical Shift Submissions |
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| Not Available | | Species |
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| Species of Origin | | Species Name | Source | Reference |
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| Amphimedon sp. | JEOL database | - Yamada, M., et al, Tetrahedron 65, 2313 (2009)
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| Chemical Taxonomy |
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| Description | Belongs to the class of organic compounds known as harmala alkaloids. Harmala alkaloids are compounds with a structure based on harmaline, harmine, harmalol, harman or a derivative of those parents. These parents are beta-carbolines, consisting of a pyrimidine fused to the pyrrole moiety of an indole to form a pyrido[3,4-b]indole. |
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| Kingdom | Organic compounds |
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| Super Class | Alkaloids and derivatives |
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| Class | Harmala alkaloids |
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| Sub Class | Not Available |
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| Direct Parent | Harmala alkaloids |
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| Alternative Parents | |
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| Substituents | - Harman
- Beta-carboline
- Pyridoindole
- Azaspirodecane
- Hydroxyindole
- 3-alkylindole
- Indole
- Indole or derivatives
- 1-hydroxy-2-unsubstituted benzenoid
- Oxepane
- Piperidine
- N-alkylpyrrolidine
- Benzenoid
- Cyclic alcohol
- Heteroaromatic compound
- Pyrrole
- Pyrrolidine
- Tertiary alcohol
- Tertiary aliphatic amine
- Tertiary amine
- Ketimine
- 1,2-aminoalcohol
- Propargyl-type 1,3-dipolar organic compound
- Organic 1,3-dipolar compound
- Organoheterocyclic compound
- Azacycle
- Oxacycle
- Dialkyl ether
- Oxirane
- Ether
- Amine
- Organopnictogen compound
- Imine
- Hydrocarbon derivative
- Alcohol
- Organic oxygen compound
- Organic nitrogen compound
- Organonitrogen compound
- Organooxygen compound
- Aromatic heteropolycyclic compound
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| Molecular Framework | Aromatic heteropolycyclic compounds |
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| External Descriptors | Not Available |
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| Physical Properties |
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| State | Not Available |
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| Experimental Properties | | Property | Value | Reference |
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| Melting Point | Not Available | Not Available | | Boiling Point | Not Available | Not Available | | Water Solubility | Not Available | Not Available | | LogP | Not Available | Not Available |
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| Predicted Properties | |
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