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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2009-07-25 00:09:23 UTC
Update Date2019-01-11 19:31:53 UTC
HMDB IDHMDB0012894
Secondary Accession Numbers
  • HMDB12894
Metabolite Identification
Common NameApelin-13
DescriptionApelin also known as APLN is a peptide which in humans is encoded by the APLN gene.[ Apelin is the endogenous ligand for the G-protein-coupled APJ receptor that is expressed at the surface of some cell types.[7] It is widely expressed in various organs such as the heart, lung, kidney, liver, adipose tissue, gastrointestinal tract, brain, adrenal glands, endothelium, and human plasma.
Structure
Data?1547235113
Synonyms
ValueSource
prepro-65-77-ApelinHMDB
Apelin-13 peptideMeSH
Chemical FormulaC69H111N23O16S
Average Molecular Weight1550.829
Monoisotopic Molecular Weight1549.829985309
IUPAC Name(2R)-2-{[(2S)-1-[(2R)-2-{[(2R)-1-{2-[(2R)-6-amino-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-{[(2R)-1-[(2S)-2-[(2S)-2-amino-4-carbamoylbutanamido]-5-[(diaminomethylidene)amino]pentanoyl]pyrrolidin-2-yl]formamido}-5-[(diaminomethylidene)amino]pentanamido]-4-methylpentanamido]-3-hydroxypropanamido]-3-(1H-imidazol-5-yl)propanamido]hexanamido]acetyl}pyrrolidin-2-yl]formamido}-4-(methylsulfanyl)butanoyl]pyrrolidin-2-yl]formamido}-3-phenylpropanoic acid
Traditional Name(2R)-2-{[(2S)-1-[(2R)-2-{[(2R)-1-{2-[(2R)-6-amino-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-{[(2R)-1-[(2S)-2-[(2S)-2-amino-4-carbamoylbutanamido]-5-[(diaminomethylidene)amino]pentanoyl]pyrrolidin-2-yl]formamido}-5-[(diaminomethylidene)amino]pentanamido]-4-methylpentanamido]-3-hydroxypropanamido]-3-(3H-imidazol-4-yl)propanamido]hexanamido]acetyl}pyrrolidin-2-yl]formamido}-4-(methylsulfanyl)butanoyl]pyrrolidin-2-yl]formamido}-3-phenylpropanoic acid
CAS Registry NumberNot Available
SMILES
CSCC[C@@H](NC(=O)[C@H]1CCCN1C(=O)CNC(=O)[C@@H](CCCCN)NC(=O)[C@H](CC1=CN=CN1)NC(=O)[C@H](CO)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCCN=C(N)N)NC(=O)[C@H]1CCCN1C(=O)[C@H](CCCN=C(N)N)NC(=O)[C@@H](N)CCC(N)=O)C(=O)N1CCC[C@H]1C(=O)N[C@H](CC1=CC=CC=C1)C(O)=O
InChI Identifier
InChI=1S/C69H111N23O16S/c1-39(2)32-47(86-58(98)44(17-9-26-78-68(73)74)83-63(103)52-20-12-29-91(52)65(105)45(18-10-27-79-69(75)76)84-56(96)42(71)22-23-54(72)94)59(99)89-50(37-93)61(101)87-48(34-41-35-77-38-81-41)60(100)82-43(16-7-8-25-70)57(97)80-36-55(95)90-28-11-19-51(90)62(102)85-46(24-31-109-3)66(106)92-30-13-21-53(92)64(104)88-49(67(107)108)33-40-14-5-4-6-15-40/h4-6,14-15,35,38-39,42-53,93H,7-13,16-34,36-37,70-71H2,1-3H3,(H2,72,94)(H,77,81)(H,80,97)(H,82,100)(H,83,103)(H,84,96)(H,85,102)(H,86,98)(H,87,101)(H,88,104)(H,89,99)(H,107,108)(H4,73,74,78)(H4,75,76,79)/t42-,43+,44-,45-,46+,47-,48-,49+,50-,51+,52+,53-/m0/s1
InChI KeyXXCCRHIAIBQDPX-YHQCEEEXSA-N
Chemical Taxonomy
DescriptionThis compound 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
  • Phenylalanine or derivatives
  • Histidine or derivatives
  • Glutamine or derivatives
  • Methionine or derivatives
  • Leucine or derivatives
  • N-acyl-alpha amino acid or derivatives
  • N-acyl-alpha-amino acid
  • Proline or derivatives
  • Serine or derivatives
  • Alpha-amino acid amide
  • 3-phenylpropanoic-acid
  • Amphetamine or derivatives
  • Alpha-amino acid or derivatives
  • N-substituted-alpha-amino acid
  • N-acylpyrrolidine
  • Pyrrolidine carboxylic acid or derivatives
  • Pyrrolidine-2-carboxamide
  • Imidazolyl carboxylic acid derivative
  • Benzenoid
  • Fatty acyl
  • Fatty amide
  • Monocyclic benzene moiety
  • N-acyl-amine
  • Azole
  • Pyrrolidine
  • Tertiary carboxylic acid amide
  • Heteroaromatic compound
  • Imidazole
  • Amino acid or derivatives
  • Amino acid
  • Carboxamide group
  • Guanidine
  • Secondary carboxylic acid amide
  • Primary carboxylic acid amide
  • Thioether
  • Carboxylic acid derivative
  • Carboxylic acid
  • Azacycle
  • Organoheterocyclic compound
  • Dialkylthioether
  • Monocarboxylic acid or derivatives
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Sulfenyl compound
  • Carboximidamide
  • Amine
  • Primary alcohol
  • Primary amine
  • Organic oxygen compound
  • Organopnictogen compound
  • Alcohol
  • Organosulfur compound
  • Primary aliphatic amine
  • Organic oxide
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Carbonyl group
  • Organonitrogen compound
  • Organooxygen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Source:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.087 g/LALOGPS
logP-1.9ALOGPS
logP-10ChemAxon
logS-4.2ALOGPS
pKa (Strongest Acidic)3.46ChemAxon
pKa (Strongest Basic)11.12ChemAxon
Physiological Charge4ChemAxon
Hydrogen Acceptor Count25ChemAxon
Hydrogen Donor Count19ChemAxon
Polar Surface Area632.97 ŲChemAxon
Rotatable Bond Count47ChemAxon
Refractivity397.32 m³·mol⁻¹ChemAxon
Polarizability162.2 ųChemAxon
Number of Rings5ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0f89-2200090000-082156889447f3345908JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0f89-6922250020-31ec08ecb438cf19de98JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0v6u-9532200100-d80feb4bb0cf4ac7c780JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-06rj-3000890000-634f1d2b6dfd4644a8f3JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-052k-9111640010-6124249b3e3cf13ec481JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0005-9202130011-7991b2aee185e1378dc9JSpectraViewer | MoNA
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB029200
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound53481538
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Zhou N, Fang J, Acheampong E, Mukhtar M, Pomerantz RJ: Binding of ALX40-4C to APJ, a CNS-based receptor, inhibits its utilization as a co-receptor by HIV-1. Virology. 2003 Jul 20;312(1):196-203. [PubMed:12890632 ]
  2. Hashimoto Y, Ishida J, Yamamoto R, Fujiwara K, Asada S, Kasuya Y, Mochizuki N, Fukamizu A: G protein-coupled APJ receptor signaling induces focal adhesion formation and cell motility. Int J Mol Med. 2005 Nov;16(5):787-92. [PubMed:16211245 ]

Enzymes

General function:
Involved in metallopeptidase activity
Specific function:
Carboxypeptidase which converts angiotensin I to angiotensin 1-9, a peptide of unknown function, and angiotensin II to angiotensin 1-7, a vasodilator. Also able to hydrolyze apelin-13 and dynorphin-13 with high efficiency. May be an important regulator of heart function. In case of human coronaviruses SARS and HCoV-NL63 infections, serve as functional receptor for the spike glycoprotein of both coronaviruses.
Gene Name:
ACE2
Uniprot ID:
Q9BYF1
Molecular weight:
92462.4