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Record Information
Version2.0
Created at2022-09-07 06:58:19 UTC
Updated at2022-09-07 06:58:19 UTC
NP-MRD IDNP0245768
Secondary Accession NumbersNone
Natural Product Identification
Common Namehitachimycin
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).
Structure
Thumb
SynonymsNot Available
Chemical FormulaC29H35NO5
Average Mass477.6010 Da
Monoisotopic Mass477.25152 Da
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
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
CAS Registry NumberNot Available
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
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
InChI KeyPLQKHNPZPRTISL-ULKJNZDWSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of OriginNot Available
Chemical Taxonomy
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.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassNot Available
Direct ParentBenzene and substituted derivatives
Alternative Parents
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
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP4.4ChemAxon
pKa (Strongest Acidic)6.46ChemAxon
pKa (Strongest Basic)4.05ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area99.35 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity143.32 m³·mol⁻¹ChemAxon
Polarizability51.95 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound101529348
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. 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 ]
  2. 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 ]
  3. 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 ]
  4. 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 ]
  5. 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 ]
  6. LOTUS database [Link]