| Record Information |
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| Version | 2.0 |
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| Created at | 2022-09-07 06:58:19 UTC |
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| Updated at | 2022-09-07 06:58:19 UTC |
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| NP-MRD ID | NP0245768 |
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| Secondary Accession Numbers | None |
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| Natural Product Identification |
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| Common Name | hitachimycin |
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| Description | (+)-Hitachimycin belongs to the class of organic compounds known as benzene and substituted derivatives. These are aromatic compounds containing one monocyclic ring system consisting of benzene. hitachimycin was first documented in 2004 (PMID: 15023978). Based on a literature review a small amount of articles have been published on (+)-Hitachimycin (PMID: 35403858) (PMID: 33625847) (PMID: 29464421) (PMID: 25786909). |
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| Structure | CO[C@H]1C[C@@H]2\C=C(\C)/C=C\C=C/C(O)=N[C@@H](C\C=C/CC[C@H](O)CC(=O)C2=C1O)C1=CC=CC=C1 InChI=1S/C29H35NO5/c1-20-11-9-10-16-27(33)30-24(21-12-5-3-6-13-21)15-8-4-7-14-23(31)19-25(32)28-22(17-20)18-26(35-2)29(28)34/h3-6,8-13,16-17,22-24,26,31,34H,7,14-15,18-19H2,1-2H3,(H,30,33)/b8-4-,11-9-,16-10-,20-17-/t22-,23-,24-,26-/m0/s1 |
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| Synonyms | Not Available |
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| Chemical Formula | C29H35NO5 |
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| Average Mass | 477.6010 Da |
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| Monoisotopic Mass | 477.25152 Da |
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| IUPAC Name | (9S,15S,19S,20aR)-7,15,18-trihydroxy-19-methoxy-2-methyl-9-phenyl-9H,10H,13H,14H,15H,16H,17H,19H,20H,20aH-cyclopenta[i]azacyclononadecan-17-one |
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| Traditional Name | (9S,15S,19S,20aR)-7,15,18-trihydroxy-19-methoxy-2-methyl-9-phenyl-9H,10H,13H,14H,15H,16H,19H,20H,20aH-cyclopenta[i]azacyclononadecan-17-one |
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| CAS Registry Number | Not Available |
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| SMILES | CO[C@H]1C[C@@H]2\C=C(\C)/C=C\C=C/C(O)=N[C@@H](C\C=C/CC[C@H](O)CC(=O)C2=C1O)C1=CC=CC=C1 |
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| InChI Identifier | InChI=1S/C29H35NO5/c1-20-11-9-10-16-27(33)30-24(21-12-5-3-6-13-21)15-8-4-7-14-23(31)19-25(32)28-22(17-20)18-26(35-2)29(28)34/h3-6,8-13,16-17,22-24,26,31,34H,7,14-15,18-19H2,1-2H3,(H,30,33)/b8-4-,11-9-,16-10-,20-17-/t22-,23-,24-,26-/m0/s1 |
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| InChI Key | PLQKHNPZPRTISL-ULKJNZDWSA-N |
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| Experimental Spectra |
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| Not Available | | 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 | Not Available |
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| Chemical Taxonomy |
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| Description | Belongs to the class of organic compounds known as benzene and substituted derivatives. These are aromatic compounds containing one monocyclic ring system consisting of benzene. |
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| Kingdom | Organic compounds |
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| Super Class | Benzenoids |
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| Class | Benzene and substituted derivatives |
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| Sub Class | Not Available |
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| Direct Parent | Benzene and substituted derivatives |
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| Alternative Parents | |
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| Substituents | - Monocyclic benzene moiety
- Vinylogous acid
- Cyclic carboximidic acid
- Secondary alcohol
- Ketone
- Azacycle
- Organoheterocyclic compound
- Organic 1,3-dipolar compound
- Propargyl-type 1,3-dipolar organic compound
- Polyol
- Ether
- Enol
- Dialkyl ether
- Organic nitrogen compound
- Organic oxygen compound
- Organopnictogen compound
- Organic oxide
- Hydrocarbon derivative
- Organooxygen compound
- Organonitrogen compound
- Carbonyl group
- Alcohol
- 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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| General References | - Rodriguez-Pena K, Gomez-Roman MP, Macias-Rubalcava ML, Rocha-Zavaleta L, Rodriguez-Sanoja R, Sanchez S: Bioinformatic comparison of three Embleya species and description of steffimycins production by Embleya sp. NF3. Appl Microbiol Biotechnol. 2022 Apr;106(8):3173-3190. doi: 10.1007/s00253-022-11915-0. Epub 2022 Apr 11. [PubMed:35403858 ]
- Kudo F, Takahashi S, Miyanaga A, Nakazawa Y, Nishino K, Hayakawa Y, Kawamura K, Ishikawa F, Tanabe G, Iwai N, Nagumo Y, Usui T, Eguchi T: Mutational Biosynthesis of Hitachimycin Analogs Controlled by the beta-Amino Acid-Selective Adenylation Enzyme HitB. ACS Chem Biol. 2021 Mar 19;16(3):539-547. doi: 10.1021/acschembio.1c00003. Epub 2021 Feb 24. [PubMed:33625847 ]
- Ottilie S, Goldgof GM, Cheung AL, Walker JL, Vigil E, Allen KE, Antonova-Koch Y, Slayman CW, Suzuki Y, Durrant JD: Two inhibitors of yeast plasma membrane ATPase 1 (ScPma1p): toward the development of novel antifungal therapies. J Cheminform. 2018 Feb 20;10(1):6. doi: 10.1186/s13321-018-0261-3. [PubMed:29464421 ]
- Kudo F, Kawamura K, Uchino A, Miyanaga A, Numakura M, Takayanagi R, Eguchi T: Genome mining of the hitachimycin biosynthetic gene cluster: involvement of a phenylalanine-2,3-aminomutase in biosynthesis. Chembiochem. 2015 Apr 13;16(6):909-14. doi: 10.1002/cbic.201500040. Epub 2015 Mar 18. [PubMed:25786909 ]
- Ping X, Takahashi Y, Seino A, Iwai Y, Omura S: Streptomyces scabrisporus sp. nov. Int J Syst Evol Microbiol. 2004 Mar;54(Pt 2):577-581. doi: 10.1099/ijs.0.02692-0. [PubMed:15023978 ]
- LOTUS database [Link]
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