ChemFOnt: Showing chemical card for Spinorphin (CFc000040261)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 19:41:39 UTC

Chemfont ID

CFc000040261

Molecule Identification

Common Name

Spinorphin

Definition

Spinorphin is an endogenous opioid heptapeptide that has the amino acid sequence Leu-Val-Val-Tyr-Pro-Trp-Thr (LVVYPWT). It has been observed to possess antinociceptive, antiallodynic and anti-inflammatory properties. The mechanism of action of spinorphin has not been fully elucidated but it has been found to act as an antagonist of the P2X3 receptor,[5] and as a weak partial agonist/antagonist of the FP1 receptor.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Leu-val-val-tyr-pro-TRP-THR	HMDB
Leucyl--valyl-valyl-tyrosyl-prolyl-tryptophyl-threonine	HMDB

Chemical Formula

C₄₅H₆₄N₈O₁₀

Average Molecular Weight

877.0373

Monoisotopic Molecular Weight

876.474540308

IUPAC Name

(2S,3R)-2-{[(2S)-2-({[(2S)-1-[(2S)-2-{[(2S)-2-{[(2S)-2-{[(2S)-2-amino-1-hydroxy-4-methylpentylidene]amino}-1-hydroxy-3-methylbutylidene]amino}-1-hydroxy-3-methylbutylidene]amino}-3-(4-hydroxyphenyl)propanoyl]pyrrolidin-2-yl](hydroxy)methylidene}amino)-1-hydroxy-3-(1H-indol-3-yl)propylidene]amino}-3-hydroxybutanoic acid

Traditional Name

spinorphin

CAS Registry Number

Not Available

SMILES

[H][C@](N)(CC(C)C)C(O)=N[C@@]([H])(C(C)C)C(O)=N[C@@]([H])(C(C)C)C(O)=N[C@@]([H])(CC1=CC=C(O)C=C1)C(=O)N1CCC[C@@]1([H])C(O)=N[C@@]([H])(CC1=CNC2=CC=CC=C12)C(O)=N[C@]([H])(C(O)=O)[C@@]([H])(C)O

InChI Identifier

InChI=1S/C45H64N8O10/c1-23(2)19-31(46)39(56)50-37(25(5)6)43(60)51-36(24(3)4)42(59)49-34(20-27-14-16-29(55)17-15-27)44(61)53-18-10-13-35(53)41(58)48-33(40(57)52-38(26(7)54)45(62)63)21-28-22-47-32-12-9-8-11-30(28)32/h8-9,11-12,14-17,22-26,31,33-38,47,54-55H,10,13,18-21,46H2,1-7H3,(H,48,58)(H,49,59)(H,50,56)(H,51,60)(H,52,57)(H,62,63)/t26-,31+,33+,34+,35+,36+,37+,38+/m1/s1

InChI Key

BXIFNVGZIMFBQB-DYDSHOKNSA-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
Leucine or derivatives
N-acyl-alpha-amino acid
Valine or derivatives
Proline or derivatives
N-acyl-l-alpha-amino acid
N-acyl-alpha amino acid or derivatives
Alpha-amino acid amide
Triptan
N-substituted-alpha-amino acid
Alpha-amino acid or derivatives
Amphetamine or derivatives
3-alkylindole
Indole or derivatives
Indole
N-acylpyrrolidine
Pyrrolidine-2-carboxamide
Pyrrolidine carboxylic acid or derivatives
1-hydroxy-2-unsubstituted benzenoid
Beta-hydroxy acid
Phenol
N-acyl-amine
Substituted pyrrole
Benzenoid
Fatty acyl
Hydroxy acid
Fatty amide
Monocyclic benzene moiety
Heteroaromatic compound
Tertiary carboxylic acid amide
Pyrrolidine
Pyrrole
Amino acid or derivatives
Amino acid
Carboxamide group
Secondary carboxylic acid amide
Secondary alcohol
Monocarboxylic acid or derivatives
Organoheterocyclic compound
Azacycle
Carboxylic acid
Organic oxygen compound
Alcohol
Organonitrogen compound
Carbonyl group
Hydrocarbon derivative
Organooxygen compound
Organic oxide
Primary amine
Primary aliphatic amine
Organic nitrogen compound
Organopnictogen compound
Amine
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0059790)

Source

Exogenous

Exogenous (HMDB: HMDB0059790)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.011 g/L	ALOGPS
logP	1.49	ALOGPS
logP	3.64	ChemAxon
logS	-4.9	ALOGPS
pKa (Strongest Acidic)	3.7	ChemAxon
pKa (Strongest Basic)	9.86	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	16	ChemAxon
Hydrogen Donor Count	10	ChemAxon
Polar Surface Area	302.83 Å²	ChemAxon
Rotatable Bond Count	21	ChemAxon
Refractivity	234.51 m³·mol⁻¹	ChemAxon
Polarizability	93.02 Å³	ChemAxon
Number of Rings	4	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

HMDB0059790

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Spinorphin

METLIN ID

Not Available

PubChem Compound

3081832

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for Spinorphin (CFc000040261)

MOL for CFc000040261 (Spinorphin)

3D MOL for CFc000040261 (Spinorphin)

3D SDF for CFc000040261 (Spinorphin)

3D-SDF for CFc000040261 (Spinorphin)

PDB for CFc000040261 (Spinorphin)

3D PDB for CFc000040261 (Spinorphin)

SMILES for CFc000040261 (Spinorphin)

INCHI for CFc000040261 (Spinorphin)

Structure for CFc000040261 (Spinorphin)

3D Structure for CFc000040261 (Spinorphin)