ChemFOnt: Showing chemical card for Valorphin (CFc000040260)

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

CFc000040260

Molecule Identification

Common Name

Valorphin

Definition

Valorphin, also known as VV-hemorphin-5, is a naturally occurring, endogenous opioid heptapeptide of the hemorphin family with the amino acid sequence Val-Val-Tyr-Pro-Trp-Thr-Gln. It is produced in the body via proteolyic cleavage of residues 33-39 of the β-chain of hemoglobin. Valorphin binds preferentially to the μ-opioid receptor and produces effects such as analgesia and self-administration in animals. Interestingly, it also possesses cytotoxic and antiproliferative properties against tumor cells.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Not Available

Chemical Formula

C₄₄H₆₀N₈O₁₂

Average Molecular Weight

892.9936

Monoisotopic Molecular Weight

892.433069424

IUPAC Name

(2S)-2-{[(2S,3R)-2-{[(2S)-2-({[(2S)-1-[(2S)-2-{[(2S)-2-{[(2S)-2-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}-1,3-dihydroxybutylidene]amino}pentanedioic acid

Traditional Name

CAS Registry Number

Not Available

SMILES

[H][C@](C)(O)[C@]([H])(N=C(O)[C@]([H])(CC1=CNC2=CC=CC=C12)N=C(O)[C@]1([H])CCCN1C(=O)[C@]([H])(CC1=CC=C(O)C=C1)N=C(O)[C@@]([H])(N=C(O)[C@@]([H])(N)C(C)C)C(C)C)C(O)=N[C@@]([H])(CCC(O)=O)C(O)=O

InChI Identifier

InChI=1S/C44H60N8O12/c1-22(2)35(45)40(59)50-36(23(3)4)41(60)49-32(19-25-12-14-27(54)15-13-25)43(62)52-18-8-11-33(52)39(58)48-31(20-26-21-46-29-10-7-6-9-28(26)29)38(57)51-37(24(5)53)42(61)47-30(44(63)64)16-17-34(55)56/h6-7,9-10,12-15,21-24,30-33,35-37,46,53-54H,8,11,16-20,45H2,1-5H3,(H,47,61)(H,48,58)(H,49,60)(H,50,59)(H,51,57)(H,55,56)(H,63,64)/t24-,30+,31+,32+,33+,35+,36+,37+/m1/s1

InChI Key

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

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Exogenous (HMDB: HMDB0059789)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.019 g/L	ALOGPS
logP	0.75	ALOGPS
logP	1.82	ChemAxon
logS	-4.7	ALOGPS
pKa (Strongest Acidic)	3.31	ChemAxon
pKa (Strongest Basic)	9.68	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	18	ChemAxon
Hydrogen Donor Count	11	ChemAxon
Polar Surface Area	340.13 Å²	ChemAxon
Rotatable Bond Count	22	ChemAxon
Refractivity	231.63 m³·mol⁻¹	ChemAxon
Polarizability	92.31 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

HMDB0059789

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

Valorphin

METLIN ID

Not Available

PubChem Compound

90470048

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for Valorphin (CFc000040260)

MOL for CFc000040260 (Valorphin)

3D MOL for CFc000040260 (Valorphin)

3D SDF for CFc000040260 (Valorphin)

3D-SDF for CFc000040260 (Valorphin)

PDB for CFc000040260 (Valorphin)

3D PDB for CFc000040260 (Valorphin)

SMILES for CFc000040260 (Valorphin)

INCHI for CFc000040260 (Valorphin)

Structure for CFc000040260 (Valorphin)

3D Structure for CFc000040260 (Valorphin)