ChemFOnt: Showing chemical card for Hemorphin-4 (CFc000040259)

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

CFc000040259

Molecule Identification

Common Name

Hemorphin-4

Definition

Hemorphin-4 is an endogenous 4-residue opioid peptide of the hemorphin family which possesses antinociceptive properties. It has the amino acid sequence Tyr-Pro-Trp-Thr. It is derived from the β-chain of hemoglobin in the bloodstream. Hemorphin-4 has affinities for the μ-, δ-, and κ-opioid receptors that are in the same range as the structurally related β-casomorphins, although affinity to the κ-opioid receptor is markedly higher in comparison. It acts as an agonist at these sites. Hemorphin-4 also has inhibitory effects on angiotensin-converting enzyme (ACE).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Tyr-pro-TRP-THR	HMDB
Tyrosyl-prolyl-tryptophyl-threonine	HMDB
Hemorphin 4	MeSH
Hemorphin-4	MeSH

Chemical Formula

C₂₉H₃₅N₅O₇

Average Molecular Weight

565.6175

Monoisotopic Molecular Weight

565.253648499

IUPAC Name

(2S,3R)-2-{[(2S)-2-({[(2S)-1-[(2S)-2-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

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

CAS Registry Number

Not Available

SMILES

[H][C@](N)(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/C29H35N5O7/c1-16(35)25(29(40)41)33-26(37)23(14-18-15-31-22-6-3-2-5-20(18)22)32-27(38)24-7-4-12-34(24)28(39)21(30)13-17-8-10-19(36)11-9-17/h2-3,5-6,8-11,15-16,21,23-25,31,35-36H,4,7,12-14,30H2,1H3,(H,32,38)(H,33,37)(H,40,41)/t16-,21+,23+,24+,25+/m1/s1

InChI Key

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

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Exogenous (HMDB: HMDB0059788)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.027 g/L	ALOGPS
logP	0.05	ALOGPS
logP	-0.16	ChemAxon
logS	-4.3	ALOGPS
pKa (Strongest Acidic)	3.43	ChemAxon
pKa (Strongest Basic)	8.02	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	205.06 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	149.39 m³·mol⁻¹	ChemAxon
Polarizability	58.47 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

HMDB0059788

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

Hemorphin-4

METLIN ID

Not Available

PubChem Compound

128444

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for Hemorphin-4 (CFc000040259)

MOL for CFc000040259 (Hemorphin-4)

3D MOL for CFc000040259 (Hemorphin-4)

3D SDF for CFc000040259 (Hemorphin-4)

3D-SDF for CFc000040259 (Hemorphin-4)

PDB for CFc000040259 (Hemorphin-4)

3D PDB for CFc000040259 (Hemorphin-4)

SMILES for CFc000040259 (Hemorphin-4)

INCHI for CFc000040259 (Hemorphin-4)

Structure for CFc000040259 (Hemorphin-4)

3D Structure for CFc000040259 (Hemorphin-4)