ChemFOnt: Showing chemical card for Oxytocin 1-8 (CFc000008170)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:54:50 UTC

Chemfont ID

CFc000008170

Molecule Identification

Common Name

Oxytocin 1-8

Definition

Oxytocin 1-8 is the fraction of Oxytocin which contains only Cys-Tyr-Ile-Gln-Asn-Cys-Pro-Leu amino acid peptide. Oxytocin (sold as Pitocin, Syntocinon) is a mammalian hormone that acts primarily as a neurotransmitter in the brain. Also known as alpha-hypophamine (α-hypophamine), oxytocin has the distinction of being the very first polypeptide hormone to be sequenced and synthesized biochemically by Vincent du Vigneaud et al. in 1953. Oxytocin is best known for its roles in female reproduction: 1) it is released in large amounts after distension of the cervix and vagina during labor, and 2) after stimulation of the nipples, facilitating birth and breastfeeding, respectively. Recent studies have begun to investigate oxytocin's role in various behaviors, including orgasm, social recognition, pair bonding, anxiety, trust, love, and maternal behaviors.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Cys-tyr-ile-GLN-asn-cys-pro-leu	HMDB
(2R)-2-({[(2R)-1-[(4S,10S,13S,16S)-19-amino-13-[(2R)-butan-2-yl]-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-pentaazacyclononadeca-5,8,11,14,17-pentaene-4-carbonyl]pyrrolidin-2-yl](hydroxy)methylidene}amino)-4-methylpentanoate	Generator

Chemical Formula

C₄₀H₆₀N₁₀O₁₂S₂

Average Molecular Weight

937.094

Monoisotopic Molecular Weight

936.383358814

IUPAC Name

(2R)-2-{[(2R)-1-[(4S,10S,13S,16S)-19-amino-13-[(2R)-butan-2-yl]-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-pentaazacyclononadecane-4-carbonyl]pyrrolidin-2-yl]formamido}-4-methylpentanoic acid

Traditional Name

(2R)-2-{[(2R)-1-[(4S,10S,13S,16S)-19-amino-13-[(2R)-butan-2-yl]-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-pentaazacyclononadecane-4-carbonyl]pyrrolidin-2-yl]formamido}-4-methylpentanoic acid

CAS Registry Number

None

SMILES

CC[C@@H](C)[C@@H]1NC(=O)[C@H](CC2=CC=C(O)C=C2)NC(=O)C(N)SSC[C@@H](NC(=O)C(CC(O)=N)NC(=O)[C@H](CCC(O)=N)NC1=O)C(=O)N1CCC[C@@H]1C(=O)N[C@H](CC(C)C)C(O)=O

InChI Identifier

InChI=1S/C40H60N10O12S2/c1-5-20(4)31-37(58)44-23(12-13-29(41)52)33(54)45-25(17-30(42)53)34(55)48-27(39(60)50-14-6-7-28(50)36(57)47-26(40(61)62)15-19(2)3)18-63-64-32(43)38(59)46-24(35(56)49-31)16-21-8-10-22(51)11-9-21/h8-11,19-20,23-28,31-32,51H,5-7,12-18,43H2,1-4H3,(H2,41,52)(H2,42,53)(H,44,58)(H,45,54)(H,46,59)(H,47,57)(H,48,55)(H,49,56)(H,61,62)/t20-,23+,24+,25?,26-,27-,28-,31+,32?/m1/s1

InChI Key

XGKIWGGRSRCBRX-YOKTWZFESA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as oligopeptides. These are organic compounds containing a sequence of between three and ten alpha-amino acids joined by peptide bonds.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Oligopeptides

Alternative Parents

Substituents

Alpha-oligopeptide
Cyclic alpha peptide
Leucine or derivatives
Macrolactam
Proline or derivatives
N-acyl-alpha-amino acid
N-acyl-alpha amino acid or derivatives
Alpha-amino acid amide
Alpha-amino acid or derivatives
N-acylpyrrolidine
Pyrrolidine carboxylic acid or derivatives
Pyrrolidine-2-carboxamide
1-hydroxy-2-unsubstituted benzenoid
Phenol
Monocyclic benzene moiety
Fatty amide
Fatty acyl
Benzenoid
Pyrrolidine
Tertiary carboxylic acid amide
Primary carboxylic acid amide
Secondary carboxylic acid amide
Organic disulfide
Carboxamide group
Lactam
Organoheterocyclic compound
Azacycle
Monocarboxylic acid or derivatives
Carboxylic acid
Organooxygen compound
Organic oxide
Organic oxygen compound
Organopnictogen compound
Primary aliphatic amine
Hydrocarbon derivative
Carbonyl group
Organic nitrogen compound
Organonitrogen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Endogenous (HMDB: HMDB0013033)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.086 g/L	ALOGPS
logP	-1.8	ALOGPS
logP	-8.3	ChemAxon
logS	-4	ALOGPS
pKa (Strongest Acidic)	-1.3	ChemAxon
pKa (Strongest Basic)	12.79	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	15	ChemAxon
Hydrogen Donor Count	13	ChemAxon
Polar Surface Area	366.62 Å²	ChemAxon
Rotatable Bond Count	15	ChemAxon
Refractivity	254.35 m³·mol⁻¹	ChemAxon
Polarizability	93.65 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

HMDB0013033

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB029259

KNApSAcK ID

Not Available

Chemspider ID

35032563

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

53481590

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for Oxytocin 1-8 (CFc000008170)

MOL for CFc000008170 (Oxytocin 1-8)

3D MOL for CFc000008170 (Oxytocin 1-8)

3D SDF for CFc000008170 (Oxytocin 1-8)

3D-SDF for CFc000008170 (Oxytocin 1-8)

PDB for CFc000008170 (Oxytocin 1-8)

3D PDB for CFc000008170 (Oxytocin 1-8)

SMILES for CFc000008170 (Oxytocin 1-8)

INCHI for CFc000008170 (Oxytocin 1-8)

Structure for CFc000008170 (Oxytocin 1-8)

3D Structure for CFc000008170 (Oxytocin 1-8)