vasopressin   Click here for help

GtoPdb Ligand ID: 2168

Abbreviated name: AVP
Synonyms: ADH | antidiuretic hormone | arginine vasopressin | argipressin
Approved drug
vasopressin is an approved drug (FDA (date of approval not specified))
Comment: The approved drug is administered as an injection, as indicated by the INN.

As with all large peptide molecules, there is some ambiguity in representations of the stereochemistry of vasopressin, therefore the chemical structure shown here may differ slightly from that shown on other resouces linked to from the table above.
Species: Human, Mouse, Rat
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2D Structure
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SMILES / InChI / InChIKey
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Canonical SMILES NC(=O)CC1NC(=O)C(CCC(=O)N)NC(=O)C(Cc2ccccc2)NC(=O)C(Cc2ccc(cc2)O)NC(=O)C(CSSCC(NC1=O)C(=O)N1CCCC1C(=O)NC(C(=O)NCC(=O)N)CCCN=C(N)N)N
Isomeric SMILES NC(=O)C[C@@H]1NC(=O)[C@H](CCC(=O)N)NC(=O)[C@H](Cc2ccccc2)NC(=O)[C@H](Cc2ccc(cc2)O)NC(=O)[C@H](CSSC[C@H](NC1=O)C(=O)N1CCC[C@H]1C(=O)N[C@H](C(=O)NCC(=O)N)CCCN=C(N)N)N
InChI InChI=1S/C46H65N15O12S2/c47-27-22-74-75-23-33(45(73)61-17-5-9-34(61)44(72)56-28(8-4-16-53-46(51)52)39(67)54-21-37(50)65)60-43(71)32(20-36(49)64)59-40(68)29(14-15-35(48)63)55-41(69)31(18-24-6-2-1-3-7-24)58-42(70)30(57-38(27)66)19-25-10-12-26(62)13-11-25/h1-3,6-7,10-13,27-34,62H,4-5,8-9,14-23,47H2,(H2,48,63)(H2,49,64)(H2,50,65)(H,54,67)(H,55,69)(H,56,72)(H,57,66)(H,58,70)(H,59,68)(H,60,71)(H4,51,52,53)/t27-,28-,29-,30-,31-,32-,33-,34-/m0/s1
InChI Key KBZOIRJILGZLEJ-LGYYRGKSSA-N
Classification Click here for help
Compound class Endogenous peptide in human, mouse or rat
Ligand families/groups Neuropeptides
Approved drug? Yes (FDA (date of approval not specified))
IUPAC Name Click here for help
(2S)-1-[(4R,7S,10S,13S,16S,19R)-19-amino-7-(2-amino-2-oxoethyl)-10-(3-amino-3-oxopropyl)-16-[(4-hydroxyphenyl)methyl]-6,9,12,15,18-pentaoxo-13-(phenylmethyl)1,2-dithia-5,8,11,14,17-pentazacycloicosane-4-carbonyl]-N-[(2S)-1-[(2-amino-2-oxoethyl)amino]-5-(diaminomethylideneamino)-1-oxopentan-2-yl]pyrrolidine-2-carboxamide
International Nonproprietary Names Click here for help
INN number INN
2144 vasopressin injection
Synonyms Click here for help
ADH | antidiuretic hormone | arginine vasopressin | argipressin
Gene/Precursor Click here for help
Gene symbol Gene name Species Precursor protein name Synonyms
AVP arginine vasopressin Human prepro-AVP-NP II (prepro-arginine-vasopressin-neurophysin II) ADH, antidiuretic hormone, ARVP, diabetes insipidus, neurohypophyseal, neurophysin II
Avp arginine vasopressin Mouse prepro-AVP-NP II (prepro-arginine-vasopressin-neurophysin II) Vp, Vsp
Avp arginine vasopressin Rat prepro-AVP-NP II (prepro-arginine-vasopressin-neurophysin II) Arginine vasopressin (Diabetes insipidus), arginine vasopressin (Diabetes insipidus) same as Di (conflicting physical mapping), arginine vasopressin (Diabetes insipidus), same as Di (conflicting physical mapping), Arginine vasopressin (Diabetes insipidus) same as Di (conflicting physical mapping), AVP-NPII, DI, prepropressophysin, preprovasopressin-neurophysin, Vas, vasopressin-neurophysin 2-copeptin, vasopressin-neurophysin prepropeptide
Database Links Click here for help
CAS Registry No. 50-56-6
CATH/Gene3D 2.60.9.10
ChEBI CHEBI:34543
ChEMBL Ligand CHEMBL373742
DrugBank Ligand DB00067
DrugCentral Ligand 2810
GtoPdb PubChem SID 135651625
PubChem CID 644077
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Search UniChem for chemical match using the InChIKey KBZOIRJILGZLEJ-LGYYRGKSSA-N
Search UniChem for chemicals with the same backbone KBZOIRJILGZLEJ
UniProtKB P01186 (Rn), P35455 (Mm), P01185 (Hs)
Wikipedia Vasopressin