Nosiheptide

Basic Info

Common NameNosiheptide(F06200)
2D Structure
FRCD IDF06200
CAS Number56377-79-8
PubChem CID70691386
FormulaC51H43N13O12S6
IUPAC Name

None

InChI Key

MQWDKYHFGBWGQZ-MQVPCCJGSA-N

InChI

InChI=1S/C51H43N13O12S6/c1-5-23-46-60-28(14-79-46)41(70)56-25-10-33(67)50(74)76-11-21-7-6-8-24-34(21)18(2)35(54-24)51(75)82-17-31(57-42(71)29-15-80-47(25)61-29)48-58-26(12-78-48)37-22(45-59-30(13-77-45)43(72)64-36(20(4)65)44(73)55-23)9-32(66)38(63-37)49-62-27(16-81-49)40(69)53-19(3)39(52)68/h5-9,12-16,20,25,31,33,36,54,62,65,67H,3,10-11,17H2,1-2,4H3,(H2,52,68)(H,53,69)(H,55,73)(H,56,70)(H,57,71)(H,64,72)/b23-5-,49-38+

Canonical SMILES

CC=C1C2=NC(=CS2)C(=O)NC3CC(C(=O)OCC4=C5C(=C(C(=O)SCC(C6=NC(=CS6)C7=NC(=C8NC(=CS8)C(=O)NC(=C)C(=O)N)C(=O)C=C7C9=NC(=CS9)C(=O)NC(C(=O)N1)C(C)O)NC(=O)C1=CSC3=N1)NC5=CC=C4)C)O

Isomeric SMILES

C/C=C\1/C2=NC(=CS2)C(=O)NC3CC(C(=O)OCC4=C5C(=C(C(=O)SCC(C6=NC(=CS6)C7=N/C(=C/8\NC(=CS8)C(=O)NC(=C)C(=O)N)/C(=O)C=C7C9=NC(=CS9)C(=O)NC(C(=O)N1)C(C)O)NC(=O)C1=CSC3=N1)NC5=CC=C4)C)O

Synonyms
        
            Nosiheptide, Antibiotic for Culture Media Use Only
        
            Nosiheptide
        
            56377-79-8
        
            Nosiheptide (USAN/INN)
        
            C12053
        
            D02392
        
            CHEMBL2103750
        
            EX-A819
        
            RP-9671
        
            377N798
Classifies
                

                  
                    Predicted: Plant Toxin
Update DateNov 13, 2018 17:07

Chemical Taxonomy

KingdomOrganic compounds
SuperclassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
SubclassAmino acids, peptides, and analogues
Intermediate Tree NodesNot available
Direct ParentPeptides
Alternative Parents
Molecular FrameworkAromatic heteropolycyclic compounds
SubstituentsAlpha peptide - N-acyl-alpha amino acid or derivatives - Indolecarboxylic acid derivative - Alpha-amino acid or derivatives - 3-alkylindole - 3-methylindole - Indole or derivatives - Indole - 2-heteroaryl carboxamide - Thiazolecarboxylic acid or derivatives - Vinylogous thioester - Substituted pyrrole - Benzenoid - Heteroaromatic compound - Vinylogous amide - Carbothioic s-lactone - Pyrrole - Thiazole - Azole - Meta-thiazoline - Thiocarboxylic acid ester - Lactam - Thioenolether - Cyclic ketone - Amino acid or derivatives - Ketone - Secondary carboxylic acid amide - Lactone - Secondary alcohol - Ketimine - Primary carboxylic acid amide - Carboxylic acid ester - Carboxamide group - Secondary aliphatic amine - Enamine - Oxacycle - Azacycle - Organoheterocyclic compound - Organic 1,3-dipolar compound - Propargyl-type 1,3-dipolar organic compound - Thiocarboxylic acid or derivatives - Secondary amine - Monocarboxylic acid or derivatives - Imine - Organic nitrogen compound - Amine - Organic oxygen compound - Organopnictogen compound - Carbonyl group - Organic oxide - Hydrocarbon derivative - Alcohol - Organooxygen compound - Organonitrogen compound - Aromatic heteropolycyclic compound
DescriptionThis compound belongs to the class of organic compounds known as peptides. These are compounds containing an amide derived from two or more amino carboxylic acid molecules (the same or different) by formation of a covalent bond from the carbonyl carbon of one to the nitrogen atom of another.

Properties

Property NameProperty Value
Molecular Weight1222.344
Hydrogen Bond Donor Count10
Hydrogen Bond Acceptor Count24
Rotatable Bond Count4
Complexity2840
Monoisotopic Mass1221.148
Exact Mass1221.148
XLogP3.8
Formal Charge0
Heavy Atom Count82
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count5
Defined Bond Stereocenter Count2
Undefined Bond Stereocenter Count0
Isotope Atom Count0
Covalently-Bonded Unit Count1

ADMET

Model Result Probability
Absorption
Blood-Brain BarrierBBB-0.9812
Human Intestinal AbsorptionHIA-0.8071
Caco-2 PermeabilityCaco2-0.6514
P-glycoprotein SubstrateSubstrate0.7752
P-glycoprotein InhibitorNon-inhibitor0.8328
Non-inhibitor0.9796
Renal Organic Cation TransporterNon-inhibitor0.8630
Distribution
Subcellular localizationMitochondria0.5184
Metabolism
CYP450 2C9 SubstrateNon-substrate0.8452
CYP450 2D6 SubstrateNon-substrate0.8170
CYP450 3A4 SubstrateSubstrate0.6471
CYP450 1A2 InhibitorNon-inhibitor0.6952
CYP450 2C9 InhibitorNon-inhibitor0.6694
CYP450 2D6 InhibitorNon-inhibitor0.8931
CYP450 2C19 InhibitorNon-inhibitor0.5956
CYP450 3A4 InhibitorNon-inhibitor0.8197
CYP Inhibitory PromiscuityLow CYP Inhibitory Promiscuity0.6954
Excretion
Toxicity
Human Ether-a-go-go-Related Gene InhibitionWeak inhibitor0.9987
Non-inhibitor0.6769
AMES ToxicityNon AMES toxic0.5704
CarcinogensNon-carcinogens0.8678
Fish ToxicityHigh FHMT0.9919
Tetrahymena Pyriformis ToxicityHigh TPT0.9810
Honey Bee ToxicityLow HBT0.6198
BiodegradationNot ready biodegradable1.0000
Acute Oral ToxicityIII0.5656
Carcinogenicity (Three-class)Non-required0.5142
Model Value Unit
Absorption
Aqueous solubility-3.1426LogS
Caco-2 Permeability0.1281LogPapp, cm/s
Distribution
Metabolism
Excretion
Toxicity
Rat Acute Toxicity2.5771LD50, mol/kg
Fish Toxicity1.1787pLC50, mg/L
Tetrahymena Pyriformis Toxicity0.5360pIGC50, ug/L

MRLs

FoodProduct CodeCountryMRLsApplication DateNotes
Chicken,Edible OffalJapan0.03ppm
Chicken,KidneyJapan0.03ppm
Chicken,LiverJapan0.03ppm
Chicken,FatJapan0.03ppm
Chicken,MuscleJapan0.03ppm
Pig,Edible OffalJapan0.03ppm
Pig,KidneyJapan0.03ppm
Pig,LiverJapan0.03ppm
Pig,FatJapan0.03ppm
Pig,MuscleJapan0.03ppm

References

TitleJournalDatePubmed ID
Nosiheptide, a sulfur-containing peptide antibiotic isolated from Streptomyces actuosus 40037.Experientia1980 Apr 157379912