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Record Information
Version1.0
Created at2022-09-02 07:25:24 UTC
Updated at2022-09-02 07:25:24 UTC
NP-MRD IDNP0151154
Secondary Accession NumbersNone
Natural Product Identification
Common Name{[(4e,6z,8r,9r,10e,12r,13s,14r,16s,17r)-3,13-dihydroxy-8,14,17-trimethoxy-4,10,12,16-tetramethyl-20,22-dioxo-2-azabicyclo[16.3.1]docosa-1(21),2,4,6,10,18-hexaen-9-yl]oxy}methanimidic acid
DescriptionHerbimycin C belongs to the class of organic compounds known as macrolactams. These are cyclic amides of amino carboxylic acids, having a 1-azacycloalkan-2-one structure, or analogues having unsaturation or heteroatoms replacing one or more carbon atoms of the ring. They are nitrogen analogues (the a nitrogen atom replacing the o atom of the cyclic carboxylic acid group ) of the naturally occurring macrolides. {[(4e,6z,8r,9r,10e,12r,13s,14r,16s,17r)-3,13-dihydroxy-8,14,17-trimethoxy-4,10,12,16-tetramethyl-20,22-dioxo-2-azabicyclo[16.3.1]docosa-1(21),2,4,6,10,18-hexaen-9-yl]oxy}methanimidic acid is found in Streptomyces hygroscopicus. It was first documented in 1986 (PMID: 3793634). Based on a literature review very few articles have been published on Herbimycin C (PMID: 3236008).
Structure
Thumb
SynonymsNot Available
Chemical FormulaC29H40N2O9
Average Mass560.6440 Da
Monoisotopic Mass560.27338 Da
IUPAC NameNot Available
Traditional NameNot Available
CAS Registry NumberNot Available
SMILES
CO[C@@H]1C[C@H](C)[C@@H](OC)C2=CC(=O)C=C(N=C(O)\C(C)=C\C=C/[C@@H](OC)[C@H](OC(O)=N)\C(C)=C\[C@@H](C)[C@@H]1O)C2=O
InChI Identifier
InChI=1S/C29H40N2O9/c1-15-9-8-10-22(37-5)27(40-29(30)36)17(3)11-16(2)24(33)23(38-6)12-18(4)26(39-7)20-13-19(32)14-21(25(20)34)31-28(15)35/h8-11,13-14,16,18,22-24,26-27,33H,12H2,1-7H3,(H2,30,36)(H,31,35)/b10-8-,15-9+,17-11+/t16-,18+,22-,23-,24+,26-,27-/m1/s1
InChI KeyDWFFHRSGCPBMKD-OZVZJJIRSA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Streptomyces hygroscopicusLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as macrolactams. These are cyclic amides of amino carboxylic acids, having a 1-azacycloalkan-2-one structure, or analogues having unsaturation or heteroatoms replacing one or more carbon atoms of the ring. They are nitrogen analogues (the a nitrogen atom replacing the o atom of the cyclic carboxylic acid group ) of the naturally occurring macrolides.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassMacrolactams
Sub ClassNot Available
Direct ParentMacrolactams
Alternative Parents
Substituents
  • Macrolactam
  • Vinylogous amide
  • Carbamic acid ester
  • Carboxamide group
  • Ketone
  • Lactam
  • Secondary alcohol
  • Secondary carboxylic acid amide
  • Cyclic ketone
  • Carboxylic acid derivative
  • Dialkyl ether
  • Ether
  • Azacycle
  • Organoheterocyclic compound
  • Organic oxide
  • Organic oxygen compound
  • Carbonyl group
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Organooxygen compound
  • Organic nitrogen compound
  • Alcohol
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic 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
logP2.16ALOGPS
logP1ChemAxon
logS-4.9ALOGPS
pKa (Strongest Acidic)-3.6ChemAxon
pKa (Strongest Basic)5.74ChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDC00017820
Chemspider ID114937482
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound6438544
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Lin LZ, Blasko G, Cordell GA: 1H-nmr analysis of herbimycins and dihydro-herbimycins. J Nat Prod. 1988 Nov-Dec;51(6):1161-5. doi: 10.1021/np50060a018. [PubMed:3236008 ]
  2. Shibata K, Satsumabayashi S, Nakagawa A, Omura S: The structure and cytocidal activity of herbimycin C. J Antibiot (Tokyo). 1986 Nov;39(11):1630-3. doi: 10.7164/antibiotics.39.1630. [PubMed:3793634 ]
  3. LOTUS database [Link]