enfuvirtide (CHEM045633)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-06-03 13:32:04 UTC
Update Date2026-04-04 18:06:01 UTC
Accession NumberCHEM045633
Identification
Common Nameenfuvirtide
ClassSmall Molecule
DescriptionA synthetic 36-amino acid peptide consisting of N-acetyltyrosyl, threonyl, seryl, leucyl, isoleucyl, histidyl, seryl, leucyl, isoleucyl, alpha-glutamyl, alpha-glutamyl, seryl, glutaminyl, asparaginyl, glutaminyl, glutaminyl, alpha-glutamyl, lysyl, asparaginyl, alpha-glutamyl, alpha-glutamyl, alpha-glutamyl, leucyl, leucyl, alpha-glutamyl, leucyl, alpha-aspartyl, lysyl, tryptophyl, alanyl, seryl, leucyl, tryptophyl, asparaginyl, tryptophyl, and phenylalaninamide residues joined in sequence. An HIV fusion inhibitor, it was the first of a novel class of antiretroviral drugs used in combination therapy for the treatment of HIV-1 infection. It interferes with entry of HIV into cells by binding to the gp41 sub-unit of the viral envelope glycoprotein, so inhibiting fusion of viral and cellular membranes.
Contaminant Sources
  • STOFF IDENT Compounds
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
Ac-ytslihslieesqnqqekneqelleldkwaslwnwf-NH2ChEBI
AcTyrThrSerLeuIleHisSerLeuIleGluGluSerGlnAsnGlnGlnGluLysAsnGluGlnGluLeuLeuGluLeuAspLysTrpAlaSerLeuTrpAsnTrpPheNH2ChEBI
PentafusideChEBI
T 20ChEBI
T-20 CPDMeSH
FuzeonMeSH
Peptide T20MeSH
T20 PeptideMeSH
Chemical FormulaC204H301N51O64
Average Molecular Mass4491.945 g/mol
Monoisotopic Mass4489.187 g/mol
CAS Registry Number159519-65-0
IUPAC Nameenfuvirtide
Traditional Nameenfuvirtide
SMILES[H][C@](C)(O)[C@]([H])(N=C(O)[C@]([H])(CC1=CC=C(O)C=C1)N=C(C)O)C(O)=N[C@@]([H])(CO)C(O)=N[C@@]([H])(CC(C)C)C(O)=N[C@]([H])(C(O)=N[C@@]([H])(CC1=CN=CN1)C(O)=N[C@@]([H])(CO)C(O)=N[C@@]([H])(CC(C)C)C(O)=N[C@]([H])(C(O)=N[C@@]([H])(CCC(O)=O)C(O)=N[C@@]([H])(CCC(O)=O)C(O)=N[C@@]([H])(CO)C(O)=N[C@@]([H])(CCC(O)=N)C(O)=N[C@@]([H])(CC(O)=N)C(O)=N[C@@]([H])(CCC(O)=N)C(O)=N[C@@]([H])(CCC(O)=N)C(O)=N[C@@]([H])(CCC(O)=O)C(O)=N[C@@]([H])(CCCCN)C(O)=N[C@@]([H])(CC(O)=N)C(O)=N[C@@]([H])(CCC(O)=O)C(O)=N[C@@]([H])(CCC(O)=N)C(O)=N[C@@]([H])(CCC(O)=O)C(O)=N[C@@]([H])(CC(C)C)C(O)=N[C@@]([H])(CC(C)C)C(O)=N[C@@]([H])(CCC(O)=O)C(O)=N[C@@]([H])(CC(C)C)C(O)=N[C@@]([H])(CC(O)=O)C(O)=N[C@@]([H])(CCCCN)C(O)=N[C@@]([H])(CC1=CNC2=CC=CC=C12)C(O)=N[C@@]([H])(C)C(O)=N[C@@]([H])(CO)C(O)=N[C@@]([H])(CC(C)C)C(O)=N[C@@]([H])(CC1=CNC2=CC=CC=C12)C(O)=N[C@@]([H])(CC(O)=N)C(O)=N[C@@]([H])(CC1=CNC2=CC=CC=C12)C(O)=N[C@@]([H])(CC1=CC=CC=C1)C(O)=N)[C@@]([H])(C)CC)[C@@]([H])(C)CC
InChI IdentifierInChI=1S/C204H301N51O64/c1-20-102(15)166(253-195(310)137(75-100(11)12)239-200(315)150(93-258)251-190(305)143(82-112-90-215-95-219-112)248-203(318)167(103(16)21-2)254-196(311)138(76-101(13)14)240-201(316)151(94-259)252-204(319)168(105(18)260)255-197(312)139(221-106(19)261)78-108-45-47-113(262)48-46-108)202(317)233-131(58-68-164(280)281)178(293)228-130(57-67-163(278)279)182(297)250-149(92-257)198(313)232-125(52-62-155(210)266)179(294)245-145(84-157(212)268)191(306)229-124(51-61-154(209)265)175(290)224-122(49-59-152(207)263)173(288)226-126(53-63-159(270)271)176(291)222-120(43-31-33-69-205)172(287)244-144(83-156(211)267)192(307)231-127(54-64-160(272)273)177(292)225-123(50-60-153(208)264)174(289)227-128(55-65-161(274)275)180(295)235-134(72-97(5)6)185(300)237-133(71-96(3)4)184(299)230-129(56-66-162(276)277)181(296)236-135(73-98(7)8)187(302)247-147(86-165(282)283)194(309)223-121(44-32-34-70-206)171(286)241-140(79-109-87-216-117-40-28-25-37-114(109)117)183(298)220-104(17)170(285)249-148(91-256)199(314)238-136(74-99(9)10)186(301)242-142(81-111-89-218-119-42-30-27-39-116(111)119)189(304)246-146(85-158(213)269)193(308)243-141(80-110-88-217-118-41-29-26-38-115(110)118)188(303)234-132(169(214)284)77-107-35-23-22-24-36-107/h22-30,35-42,45-48,87-90,95-105,120-151,166-168,216-218,256-260,262H,20-21,31-34,43-44,49-86,91-94,205-206H2,1-19H3,(H2,207,263)(H2,208,264)(H2,209,265)(H2,210,266)(H2,211,267)(H2,212,268)(H2,213,269)(H2,214,284)(H,215,219)(H,220,298)(H,221,261)(H,222,291)(H,223,309)(H,224,290)(H,225,292)(H,226,288)(H,227,289)(H,228,293)(H,229,306)(H,230,299)(H,231,307)(H,232,313)(H,233,317)(H,234,303)(H,235,295)(H,236,296)(H,237,300)(H,238,314)(H,239,315)(H,240,316)(H,241,286)(H,242,301)(H,243,308)(H,244,287)(H,245,294)(H,246,304)(H,247,302)(H,248,318)(H,249,285)(H,250,297)(H,251,305)(H,252,319)(H,253,310)(H,254,311)(H,255,312)(H,270,271)(H,272,273)(H,274,275)(H,276,277)(H,278,279)(H,280,281)(H,282,283)/t102-,103-,104-,105+,120-,121-,122-,123-,124-,125-,126-,127-,128-,129-,130-,131-,132-,133-,134-,135-,136-,137-,138-,139-,140-,141-,142-,143-,144-,145-,146-,147-,148-,149-,150-,151-,166-,167-,168-/m0/s1
InChI KeyPEASPLKKXBYDKL-FXEVSJAOSA-N
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
  • Alpha peptide
  • Tyrosine or derivatives
  • Phenylalanine or derivatives
  • Histidine or derivatives
  • Glutamic acid or derivatives
  • Glutamine or derivatives
  • Leucine or derivatives
  • Isoleucine or derivatives
  • Aspartic acid or derivatives
  • Asparagine or derivatives
  • N-acyl-alpha amino acid or derivatives
  • Serine or derivatives
  • Triptan
  • Alpha-amino acid amide
  • Alanine or derivatives
  • 3-alkylindole
  • N-substituted-alpha-amino acid
  • Alpha-amino acid or derivatives
  • Amphetamine or derivatives
  • Indole
  • Indole or derivatives
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Monocyclic benzene moiety
  • Fatty amide
  • N-acyl-amine
  • Substituted pyrrole
  • Fatty acyl
  • Benzenoid
  • Pyrrole
  • Acetamide
  • Heteroaromatic compound
  • Azole
  • Imidazole
  • Primary carboxylic acid amide
  • Amino acid or derivatives
  • Secondary carboxylic acid amide
  • Secondary alcohol
  • Carboxamide group
  • Amino acid
  • Organoheterocyclic compound
  • Azacycle
  • Carboxylic acid derivative
  • Carboxylic acid
  • Primary amine
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Primary aliphatic amine
  • Carbonyl group
  • Alcohol
  • Organic oxygen compound
  • Organic oxide
  • Organonitrogen compound
  • Organooxygen compound
  • Organopnictogen compound
  • Amine
  • Primary alcohol
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
logP16.58ChemAxon
pKa (Strongest Acidic)2.46ChemAxon
Physiological Charge-9ChemAxon
Hydrogen Acceptor Count111ChemAxon
Hydrogen Donor Count71ChemAxon
Polar Surface Area2036.45 ŲChemAxon
Rotatable Bond Count151ChemAxon
Refractivity1220.14 m³·mol⁻¹ChemAxon
Polarizability469.24 ųChemAxon
Number of Rings9ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
SpectraNot Available
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDNot Available
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkEnfuvirtide
Chemspider IDNot Available
ChEBI ID608828
PubChem Compound ID16130199
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=17485501
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=25017682