Hmdb loader
You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version5.0
StatusDetected and Quantified
Creation Date2009-07-25 00:09:24 UTC
Update Date2021-09-14 15:19:50 UTC
HMDB IDHMDB0012895
Secondary Accession Numbers
  • HMDB12895
Metabolite Identification
Common NameArginine vasopressin 1-8
DescriptionArginine vasopressin (AVP), also known as vasopressin, argipressin or antidiuretic hormone (ADH), is a hormone found in most mammals, including humans. Vasopressin is a peptide hormone that controls the reabsorption of molecules in the tubules of the kidneys by affecting the tissue's permeability. It also increases peripheral vascular resistance, which in turn increases arterial blood pressure. It plays a key role in homeostasis, and the regulation of water, glucose, and salts in the blood. It is derived from a preprohormone precursor that is synthesized in the hypothalamus and stored in vesicles at the posterior pituitary. Most of it is stored in the posterior pituitary to be released into the bloodstream; however, some AVP is also released directly into the brain. This is a sample structure of fraction 1-8 of the peptide chain.
Structure
Data?1582753076
Synonyms
ValueSource
Cys-tyr-phe-GLN-asn-cys-pro-argHMDB
Des-gly-NH(,2)('9),[arg('8)]-vasopressinHMDB
(2R)-2-({[(2R)-1-[(4R,10R,13R,16R)-19-amino-13-benzyl-6,9,12,15,18-pentahydroxy-10-[2-(C-hydroxycarbonimidoyl)ethyl]-7-[(C-hydroxycarbonimidoyl)methyl]-16-[(4-hydroxyphenyl)methyl]-1,2-dithia-5,8,11,14,17-pentaazacycloicosa-5,8,11,14,17-pentaene-4-carbonyl]pyrrolidin-2-yl](hydroxy)methylidene}amino)-5-carbamimidamidopentanoateGenerator
Chemical FormulaC44H61N13O12S2
Average Molecular Weight1028.165
Monoisotopic Molecular Weight1027.400405861
IUPAC Name(2R)-2-{[(2R)-1-[(4R,10R,13R,16R)-19-amino-13-benzyl-10-[2-(C-hydroxycarbonimidoyl)ethyl]-7-[(C-hydroxycarbonimidoyl)methyl]-16-[(4-hydroxyphenyl)methyl]-6,9,12,15,18-pentaoxo-1,2-dithia-5,8,11,14,17-pentaazacycloicosane-4-carbonyl]pyrrolidin-2-yl]formamido}-5-carbamimidamidopentanoic acid
Traditional Name(2R)-2-{[(2R)-1-[(4R,10R,13R,16R)-19-amino-13-benzyl-10-[2-(C-hydroxycarbonimidoyl)ethyl]-7-(C-hydroxycarbonimidoylmethyl)-16-[(4-hydroxyphenyl)methyl]-6,9,12,15,18-pentaoxo-1,2-dithia-5,8,11,14,17-pentaazacycloicosane-4-carbonyl]pyrrolidin-2-yl]formamido}-5-carbamimidamidopentanoic acid
CAS Registry Number37552-33-3
SMILES
NC1CSSC[C@H](NC(=O)C(CC(O)=N)NC(=O)[C@@H](CCC(O)=N)NC(=O)[C@@H](CC2=CC=CC=C2)NC(=O)[C@@H](CC2=CC=C(O)C=C2)NC1=O)C(=O)N1CCC[C@@H]1C(=O)N[C@H](CCCNC(N)=N)C(O)=O
InChI Identifier
InChI=1S/C44H61N13O12S2/c45-26-21-70-71-22-32(42(67)57-17-5-9-33(57)41(66)52-28(43(68)69)8-4-16-50-44(48)49)56-40(65)31(20-35(47)60)55-37(62)27(14-15-34(46)59)51-38(63)30(18-23-6-2-1-3-7-23)54-39(64)29(53-36(26)61)19-24-10-12-25(58)13-11-24/h1-3,6-7,10-13,26-33,58H,4-5,8-9,14-22,45H2,(H2,46,59)(H2,47,60)(H,51,63)(H,52,66)(H,53,61)(H,54,64)(H,55,62)(H,56,65)(H,68,69)(H4,48,49,50)/t26?,27-,28-,29-,30-,31?,32+,33-/m1/s1
InChI KeySXYIOPJBWYQZRQ-VMPYSSHJSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as long-chain 3-enoyl coas. These are organic compounds containing a coenzyme A substructure linked to a long-chain 3-enoyl chain of 13 to 21 carbon atoms.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acyl thioesters
Direct ParentLong-chain 3-enoyl CoAs
Alternative Parents
Substituents
  • Coenzyme a or derivatives
  • Purine ribonucleoside 3',5'-bisphosphate
  • Purine ribonucleoside bisphosphate
  • Purine ribonucleoside diphosphate
  • Ribonucleoside 3'-phosphate
  • Pentose phosphate
  • Pentose-5-phosphate
  • Octadecanoid
  • Long-chain fatty acid
  • Cysteine or derivatives
  • Glycosyl compound
  • N-glycosyl compound
  • Alpha-amino acid
  • Alpha-amino acid or derivatives
  • 6-aminopurine
  • Monosaccharide phosphate
  • Organic pyrophosphate
  • Pentose monosaccharide
  • Imidazopyrimidine
  • Purine
  • Aminopyrimidine
  • Hydroxy fatty acid
  • Monoalkyl phosphate
  • Thia fatty acid
  • Fatty acid
  • Imidolactam
  • Dicarboxylic acid or derivatives
  • Alkyl phosphate
  • Monosaccharide
  • N-substituted imidazole
  • Organic phosphoric acid derivative
  • Unsaturated fatty acid
  • Phosphoric acid ester
  • Pyrimidine
  • Imidazole
  • Oxolane
  • Azole
  • Heteroaromatic compound
  • Amino acid
  • Secondary alcohol
  • Thiocarboxylic acid ester
  • Carbothioic s-ester
  • Amino acid or derivatives
  • Dialkylthioether
  • Sulfenyl compound
  • Oxacycle
  • Thioether
  • Carboximidic acid
  • Azacycle
  • Thiocarboxylic acid or derivatives
  • Propargyl-type 1,3-dipolar organic compound
  • Carboximidic acid derivative
  • Organic 1,3-dipolar compound
  • Organoheterocyclic compound
  • Carboxylic acid derivative
  • Carboxylic acid
  • Hydrocarbon derivative
  • Organic nitrogen compound
  • Alcohol
  • Organic oxygen compound
  • Organic oxide
  • Primary aliphatic amine
  • Primary amine
  • Amine
  • Organonitrogen compound
  • Organooxygen compound
  • Carbonyl group
  • Organosulfur compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.091 g/LALOGPS
logP-1.7ALOGPS
logP-10ChemAxon
logS-4ALOGPS
pKa (Strongest Acidic)-1.3ChemAxon
pKa (Strongest Basic)12.79ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count18ChemAxon
Hydrogen Donor Count16ChemAxon
Polar Surface Area428.52 ŲChemAxon
Rotatable Bond Count17ChemAxon
Refractivity290.13 m³·mol⁻¹ChemAxon
Polarizability102.37 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+325.31830932474
DeepCCS[M-H]-323.59530932474
DeepCCS[M-2H]-357.62930932474
DeepCCS[M+Na]+331.64830932474
AllCCS[M+H]+300.932859911
AllCCS[M+H-H2O]+301.932859911
AllCCS[M+NH4]+300.032859911
AllCCS[M+Na]+299.832859911
AllCCS[M-H]-259.832859911
AllCCS[M+Na-2H]-265.032859911
AllCCS[M+HCOO]-270.732859911

Predicted Kovats Retention Indices

Not Available
Spectra

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Arginine vasopressin 1-8 10V, Positive-QTOFsplash10-03di-9110000025-1d304e1782b2b92911982017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Arginine vasopressin 1-8 20V, Positive-QTOFsplash10-03fr-9410000648-470eae3d17a7f7d705bb2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Arginine vasopressin 1-8 40V, Positive-QTOFsplash10-0229-9100000100-4b40efe5af3314f71a4b2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Arginine vasopressin 1-8 10V, Negative-QTOFsplash10-0a7i-8000000009-b503dd2d74647ca7d0852017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Arginine vasopressin 1-8 20V, Negative-QTOFsplash10-0a4l-9110000017-bd06143bf9064ccc775e2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Arginine vasopressin 1-8 40V, Negative-QTOFsplash10-052f-9100000000-4e293036f769e50bf0f82017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Arginine vasopressin 1-8 10V, Negative-QTOFsplash10-004i-9000000001-b63902d3b4c23aa08ec72021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Arginine vasopressin 1-8 20V, Negative-QTOFsplash10-05mo-6100000009-7777e6244da2676c85ac2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Arginine vasopressin 1-8 40V, Negative-QTOFsplash10-0006-9100000010-2cc8a7f561fd1c804ae02021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Arginine vasopressin 1-8 10V, Positive-QTOFsplash10-01t9-9000000020-ae807e7e466480b191d62021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Arginine vasopressin 1-8 20V, Positive-QTOFsplash10-03e9-9010000315-5e0e5a761015a74ef4fa2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Arginine vasopressin 1-8 40V, Positive-QTOFsplash10-01x3-6200000930-54c5785551341cad6b322021-09-24Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Cerebrospinal Fluid (CSF)
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
Cerebrospinal Fluid (CSF)Detected and Quantified0.0000292 +/- 0.0000029 uMAdult (>18 years old)Not SpecifiedNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified0.0000040000 +/- 0.0000002528 uMNot SpecifiedNot SpecifiedNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
Cerebrospinal Fluid (CSF)Detected and Quantified0.0000268 +/- 0.000006 uMAdult (>18 years old)Not SpecifiedPrader-Willi syndrome details
Cerebrospinal Fluid (CSF)Detected and Quantified0.0000006904 +/- 0.0000001556 uMAdult (>18 years old)Not SpecifiedFebrile seizure details
Cerebrospinal Fluid (CSF)Detected and Quantified0.0000007779 +/- 0.0000004376 uMAdult (>18 years old)Not SpecifiedConvulsive disorder details
Cerebrospinal Fluid (CSF)Detected and Quantified0.0000008265 +/- 0.0000003403 uMAdult (>18 years old)Not SpecifiedMiscellaneous infectious diseases details
Cerebrospinal Fluid (CSF)Detected and Quantified0.00003365 +/- 0.000020000 uMNot SpecifiedNot SpecifiedTraumatic subarachnoid hemorrhage details
Associated Disorders and Diseases
Disease References
Prader-Willi syndrome
  1. Martin A, State M, Anderson GM, Kaye WM, Hanchett JM, McConaha CW, North WG, Leckman JF: Cerebrospinal fluid levels of oxytocin in Prader-Willi syndrome: a preliminary report. Biol Psychiatry. 1998 Dec 15;44(12):1349-52. [PubMed:9861478 ]
Febrile seizures
  1. Cotton MF, Donald PR, Aalbers C: Arginine vasopressin concentrations in the cerebrospinal fluid of children. Childs Nerv Syst. 1991 Nov;7(7):399-401. [PubMed:1794121 ]
Convulsion
  1. Cotton MF, Donald PR, Aalbers C: Arginine vasopressin concentrations in the cerebrospinal fluid of children. Childs Nerv Syst. 1991 Nov;7(7):399-401. [PubMed:1794121 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB029201
KNApSAcK IDNot Available
Chemspider ID35032552
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound53481539
PDB IDNot Available
ChEBI ID89492
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDMDB00029856
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available