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Record Information
Version1.0
Created at2021-01-05 20:42:07 UTC
Updated at2021-07-15 17:07:23 UTC
NP-MRD IDNP0010898
Secondary Accession NumbersNone
Natural Product Identification
Common NameCatenulipeptin
Provided ByNPAtlasNPAtlas Logo
Description(2S)-2-{[(2S)-2-({[(3S,9S,11R,15R,18S,21S)-9-{[(2S)-2-[(2-{[(2S)-2-({[(3S,9S,11R,15R,21S,24S)-9-{[(2S)-2-[(2-{[2-({2-[(2-{[(2S)-2-[(2-amino-1-hydroxyethylidene)amino]-1-hydroxy-3-(1H-imidazol-5-yl)propylidene]amino}-1-hydroxyethylidene)amino]-1-hydroxyethylidene}amino)-1-hydroxyethylidene]amino}-1-hydroxyethylidene)amino]-3-carboxy-1-hydroxypropylidene]amino}-2,5,8,17,20,23,26-heptahydroxy-21-[(1R)-1-hydroxyethyl]-3-(2-methylpropyl)-24-(propan-2-yl)-13-thia-1,4,7,16,19,22,25-heptaazaspiro[10.15]Hexacosa-1,4,7,16,19,22,25-heptaen-15-yl](hydroxy)methylidene}amino)-1-hydroxy-3-(C-hydroxycarbonimidoyl)propylidene]amino}-1-hydroxyethylidene)amino]-1-hydroxy-3-(1H-imidazol-5-yl)propylidene]amino}-3-[(2S)-butan-2-yl]-2,5,8,17,20,23-hexahydroxy-18,21-bis(2-methylpropyl)-13-thia-1,4,7,16,19,22-hexaazaspiro[10.12]Tricosa-1,4,7,16,19,22-hexaen-15-yl](hydroxy)methylidene}amino)-3-carboxy-1-hydroxypropylidene]amino}-4-methylpentanoic acid belongs to the class of organic compounds known as polypeptides. These are peptides containing ten or more amino acid residues. Catenulipeptin is found in Catenulispora acidiphila DSM 44928. It was first documented in 2012 (PMID: 22725258). Based on a literature review very few articles have been published on (2S)-2-{[(2S)-2-({[(3S,9S,11R,15R,18S,21S)-9-{[(2S)-2-[(2-{[(2S)-2-({[(3S,9S,11R,15R,21S,24S)-9-{[(2S)-2-[(2-{[2-({2-[(2-{[(2S)-2-[(2-amino-1-hydroxyethylidene)amino]-1-hydroxy-3-(1H-imidazol-5-yl)propylidene]amino}-1-hydroxyethylidene)amino]-1-hydroxyethylidene}amino)-1-hydroxyethylidene]amino}-1-hydroxyethylidene)amino]-3-carboxy-1-hydroxypropylidene]amino}-2,5,8,17,20,23,26-heptahydroxy-21-[(1R)-1-hydroxyethyl]-3-(2-methylpropyl)-24-(propan-2-yl)-13-thia-1,4,7,16,19,22,25-heptaazaspiro[10.15]Hexacosa-1,4,7,16,19,22,25-heptaen-15-yl](hydroxy)methylidene}amino)-1-hydroxy-3-(C-hydroxycarbonimidoyl)propylidene]amino}-1-hydroxyethylidene)amino]-1-hydroxy-3-(1H-imidazol-5-yl)propylidene]amino}-3-[(2S)-butan-2-yl]-2,5,8,17,20,23-hexahydroxy-18,21-bis(2-methylpropyl)-13-thia-1,4,7,16,19,22-hexaazaspiro[10.12]Tricosa-1,4,7,16,19,22-hexaen-15-yl](hydroxy)methylidene}amino)-3-carboxy-1-hydroxypropylidene]amino}-4-methylpentanoic acid (PMID: 34383398) (PMID: 34383397) (PMID: 34383396) (PMID: 34384147).
Structure
Thumb
Synonyms
ValueSource
(2S)-2-{[(2S)-2-({[(3S,9S,11R,15R,18S,21S)-9-{[(2S)-2-[(2-{[(2S)-2-({[(3S,9S,11R,15R,21S,24S)-9-{[(2S)-2-[(2-{[2-({2-[(2-{[(2S)-2-[(2-amino-1-hydroxyethylidene)amino]-1-hydroxy-3-(1H-imidazol-5-yl)propylidene]amino}-1-hydroxyethylidene)amino]-1-hydroxyethylidene}amino)-1-hydroxyethylidene]amino}-1-hydroxyethylidene)amino]-3-carboxy-1-hydroxypropylidene]amino}-2,5,8,17,20,23,26-heptahydroxy-21-[(1R)-1-hydroxyethyl]-3-(2-methylpropyl)-24-(propan-2-yl)-13-thia-1,4,7,16,19,22,25-heptaazaspiro[10.15]hexacosa-1,4,7,16,19,22,25-heptaen-15-yl](hydroxy)methylidene}amino)-1-hydroxy-3-(C-hydroxycarbonimidoyl)propylidene]amino}-1-hydroxyethylidene)amino]-1-hydroxy-3-(1H-imidazol-5-yl)propylidene]amino}-3-[(2S)-butan-2-yl]-2,5,8,17,20,23-hexahydroxy-18,21-bis(2-methylpropyl)-13-thia-1,4,7,16,19,22-hexaazaspiro[10.12]tricosa-1,4,7,16,19,22-hexaen-15-yl](hydroxy)methylidene}amino)-3-carboxy-1-hydroxypropylidene]amino}-4-methylpentanoateGenerator
Chemical FormulaC99H152N32O34S2
Average Mass2398.6200 Da
Monoisotopic Mass2397.05901 Da
IUPAC Name(2S)-2-[(2S)-2-{[(3S,9S,11R,15R,18S,21S)-9-[(2S)-2-{2-[(2S)-2-{[(3S,9S,11R,15R,21S,24S)-9-[(2S)-2-{2-[2-(2-{2-[(2S)-2-(2-aminoacetamido)-3-(1H-imidazol-5-yl)propanamido]acetamido}acetamido)acetamido]acetamido}-3-carboxypropanamido]-21-[(1R)-1-hydroxyethyl]-3-(2-methylpropyl)-2,5,8,17,20,23,26-heptaoxo-24-(propan-2-yl)-13-thia-1,4,7,16,19,22,25-heptaazaspiro[10.15]hexacosan-15-yl]formamido}-3-carbamoylpropanamido]acetamido}-3-(1H-imidazol-5-yl)propanamido]-3-[(2S)-butan-2-yl]-18,21-bis(2-methylpropyl)-2,5,8,17,20,23-hexaoxo-13-thia-1,4,7,16,19,22-hexaazaspiro[10.12]tricosan-15-yl]formamido}-3-carboxypropanamido]-4-methylpentanoic acid
Traditional Name(2S)-2-[(2S)-2-{[(3S,9S,11R,15R,18S,21S)-9-[(2S)-2-{2-[(2S)-2-{[(3S,9S,11R,15R,21S,24S)-9-[(2S)-2-{2-[2-(2-{2-[(2S)-2-(2-aminoacetamido)-3-(3H-imidazol-4-yl)propanamido]acetamido}acetamido)acetamido]acetamido}-3-carboxypropanamido]-21-[(1R)-1-hydroxyethyl]-24-isopropyl-3-(2-methylpropyl)-2,5,8,17,20,23,26-heptaoxo-13-thia-1,4,7,16,19,22,25-heptaazaspiro[10.15]hexacosan-15-yl]formamido}-3-carbamoylpropanamido]acetamido}-3-(3H-imidazol-4-yl)propanamido]-3-[(2S)-butan-2-yl]-18,21-bis(2-methylpropyl)-2,5,8,17,20,23-hexaoxo-13-thia-1,4,7,16,19,22-hexaazaspiro[10.12]tricosan-15-yl]formamido}-3-carboxypropanamido]-4-methylpentanoic acid
CAS Registry NumberNot Available
SMILES
CC[C@H](C)[C@@H]1NC(=O)CNC(=O)[C@H](C[C@@]2(CSC[C@H](NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC(C)C)NC2=O)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CC(C)C)C(O)=O)NC1=O)NC(=O)[C@H](CC1=CN=CN1)NC(=O)CNC(=O)[C@H](CC(N)=O)NC(=O)[C@@H]1CSC[C@@]2(C[C@H](NC(=O)[C@H](CC(O)=O)NC(=O)CNC(=O)CNC(=O)CNC(=O)CNC(=O)[C@H](CC3=CN=CN3)NC(=O)CN)C(=O)NCC(=O)N[C@@H](CC(C)C)C(=O)N2)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H]([C@@H](C)O)C(=O)NCC(=O)N1
InChI Identifier
InChI=1S/C99H152N32O34S2/c1-14-48(12)78-94(161)131-98(39-167-38-64(90(157)121-59(23-76(145)146)88(155)122-60(95(162)163)18-46(8)9)125-84(151)52(15-43(2)3)119-85(152)53(16-44(4)5)126-96(98)164)24-61(83(150)110-36-74(142)127-78)123-86(153)56(20-51-28-103-42-113-51)116-72(140)33-108-81(148)57(21-65(101)133)120-89(156)63-37-166-40-99(97(165)129-77(47(10)11)93(160)128-79(49(13)132)92(159)111-35-73(141)118-63)25-62(82(149)109-34-71(139)115-54(17-45(6)7)91(158)130-99)124-87(154)58(22-75(143)144)117-70(138)32-106-68(136)30-104-67(135)29-105-69(137)31-107-80(147)55(114-66(134)26-100)19-50-27-102-41-112-50/h27-28,41-49,52-64,77-79,132H,14-26,29-40,100H2,1-13H3,(H2,101,133)(H,102,112)(H,103,113)(H,104,135)(H,105,137)(H,106,136)(H,107,147)(H,108,148)(H,109,149)(H,110,150)(H,111,159)(H,114,134)(H,115,139)(H,116,140)(H,117,138)(H,118,141)(H,119,152)(H,120,156)(H,121,157)(H,122,155)(H,123,153)(H,124,154)(H,125,151)(H,126,164)(H,127,142)(H,128,160)(H,129,165)(H,130,158)(H,131,161)(H,143,144)(H,145,146)(H,162,163)/t48-,49+,52-,53-,54-,55-,56-,57-,58-,59-,60-,61-,62-,63-,64-,77-,78-,79-,98-,99-/m0/s1
InChI KeyAXDPBAOMGSGZMT-PMTSSQHDSA-N
Spectra
Spectrum TypeDescriptionDepositor IDDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
Species
Species of Origin
Species NameSourceReference
Catenulispora acidiphila DSM 44928
Chemical Taxonomy
Description Belongs to the class of organic compounds known as polypeptides. These are peptides containing ten or more amino acid residues.
KingdomOrganic compounds
Super ClassOrganic Polymers
ClassPolypeptides
Sub ClassNot Available
Direct ParentPolypeptides
Alternative Parents
Substituents
  • Polypeptide
  • Cyclic alpha peptide
  • Histidine or derivatives
  • Leucine or derivatives
  • Aspartic acid or derivatives
  • Asparagine or derivatives
  • N-acyl-alpha amino acid or derivatives
  • N-acyl-alpha-amino acid
  • N-acyl-l-alpha-amino acid
  • Alpha-amino acid amide
  • N-substituted-alpha-amino acid
  • Alpha-amino acid or derivatives
  • Tricarboxylic acid or derivatives
  • N-acyl-amine
  • Fatty acyl
  • Fatty amide
  • Imidazole
  • Azole
  • Heteroaromatic compound
  • Secondary carboxylic acid amide
  • Secondary alcohol
  • Primary carboxylic acid amide
  • Lactam
  • Carboxamide group
  • Amino acid
  • Amino acid or derivatives
  • Azacycle
  • Carboxylic acid derivative
  • Carboxylic acid
  • Organoheterocyclic compound
  • Dialkylthioether
  • Thioether
  • Organopnictogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Alcohol
  • Carbonyl group
  • Hydrocarbon derivative
  • Amine
  • Organic oxide
  • Primary amine
  • Primary aliphatic amine
  • Organooxygen compound
  • Organonitrogen compound
  • 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
logP-24ChemAxon
pKa (Strongest Acidic)3.09ChemAxon
pKa (Strongest Basic)7.9ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count37ChemAxon
Hydrogen Donor Count34ChemAxon
Polar Surface Area1015.2 ŲChemAxon
Rotatable Bond Count49ChemAxon
Refractivity576.04 m³·mol⁻¹ChemAxon
Polarizability237.23 ųChemAxon
Number of Rings6ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID78442587
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound139585188
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Wang H, van der Donk WA: Biosynthesis of the class III lantipeptide catenulipeptin. ACS Chem Biol. 2012 Sep 21;7(9):1529-35. doi: 10.1021/cb3002446. Epub 2012 Jul 2. [PubMed:22725258 ]
  2. Mitchell PM: The cost-effectiveness of what in health and care?. 2021 Feb. [PubMed:34383398 ]
  3. Authors unspecified: Ozanimod. 2012. [PubMed:34383397 ]
  4. Authors unspecified: Ponesimod. 2012. [PubMed:34383396 ]
  5. Lee J, Cho Y, Choi KH, Hwang I, Oh YL: Metastatic leiomyosarcoma of the thyroid gland: cytologic findings and differential diagnosis. J Pathol Transl Med. 2021 Aug 13. pii: jptm.2021.06.23. doi: 10.4132/jptm.2021.06.23. [PubMed:34384147 ]