Showing Compound Intermedine (FDB004288)

Record Information

Version

1.0

Creation date

2010-04-08 22:06:10 UTC

Update date

2019-11-26 02:59:55 UTC

Primary ID

FDB004288

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Intermedine

Description

Intermedine, also known as 9-(+)-trachelanthylretronecine or beta-msh, belongs to alkaloids and derivatives class of compounds. Those are naturally occurring chemical compounds that contain mostly basic nitrogen atoms. This group also includes some related compounds with neutral and even weakly acidic propertiesand is also some synthetic compounds of similar structure are attributed to alkaloids. In addition to carbon, hydrogen and nitrogen, alkaloids may also contain oxygen, sulfur and more rarely other elements such as chlorine, bromine, and phosphorus. Intermedine is soluble (in water) and a very weakly acidic compound (based on its pKa). Intermedine can be found in borage, which makes intermedine a potential biomarker for the consumption of this food product.

CAS Number

10285-06-0

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
9-(+)-Trachelanthylretronecine	ChEBI
beta-MSH	ChEBI
Intermedina	ChEBI
Intermedinum	ChEBI
b-MSH	Generator
Β-MSH	Generator
Beta-melanocyte-stimulating hormone	biospider
Beta-melanotropin	biospider
Beta-MSH	biospider
Intermedin	biospider
Intermedine	biospider
Mel-stimulating hormone	biospider
Melanocyte stimulating hormones	biospider
Melanocyte-stimulating hormones	biospider
Melanophore hormone	biospider
Melanophore stimulating hormone	biospider
Melanophore-expanding hormone	biospider
Melanophore-stimulating hormone	biospider
Melanotropin	biospider
MSH	biospider
MSH (melanocyte-stimulating hormones)	biospider
Pigment hormone	biospider

Predicted Properties

Property	Value	Source
Water Solubility	50.8 g/L	ALOGPS
logP	0.41	ALOGPS
logP	-0.29	ChemAxon
logS	-0.77	ALOGPS
pKa (Strongest Acidic)	11.34	ChemAxon
pKa (Strongest Basic)	8.82	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	90.23 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	77.94 m³·mol⁻¹	ChemAxon
Polarizability	31.65 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C15H25NO5

IUPAC name

[(1R,7aR)-1-hydroxy-2,3,5,7a-tetrahydro-1H-pyrrolizin-7-yl]methyl (2S)-2-hydroxy-2-[(1R)-1-hydroxyethyl]-3-methylbutanoate

InChI Identifier

InChI=1S/C15H25NO5/c1-9(2)15(20,10(3)17)14(19)21-8-11-4-6-16-7-5-12(18)13(11)16/h4,9-10,12-13,17-18,20H,5-8H2,1-3H3/t10-,12-,13-,15+/m1/s1

InChI Key

SFVVQRJOGUKCEG-OPQSFPLASA-N

Isomeric SMILES

[H][C@@]12[C@H](O)CCN1CC=C2COC(=O)[C@](O)(C(C)C)[C@@H](C)O

Average Molecular Weight

299.3627

Monoisotopic Molecular Weight

299.173272915

Classification

Description

Belongs to the class of organic compounds known as alkaloids and derivatives. These are naturally occurring chemical compounds that contain mostly basic nitrogen atoms. This group also includes some related compounds with neutral and even weakly acidic properties. Also some synthetic compounds of similar structure are attributed to alkaloids. In addition to carbon, hydrogen and nitrogen, alkaloids may also contain oxygen, sulfur and more rarely other elements such as chlorine, bromine, and phosphorus.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Not Available

Sub Class

Not Available

Direct Parent

Alkaloids and derivatives

Alternative Parents

Substituents

Alkaloid or derivatives
Pyrrolizine
Beta-hydroxy acid
Fatty acid ester
Hydroxy acid
N-alkylpyrrolidine
Fatty acyl
Tertiary alcohol
Pyrroline
Pyrrolidine
Amino acid or derivatives
Tertiary aliphatic amine
Tertiary amine
Secondary alcohol
Carboxylic acid ester
Azacycle
Organoheterocyclic compound
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Hydrocarbon derivative
Organonitrogen compound
Alcohol
Organic oxygen compound
Organooxygen compound
Organopnictogen compound
Carbonyl group
Organic nitrogen compound
Organic oxide
Amine
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

azabicycloalkane (CHEBI:5941 )
carboxylic ester (CHEBI:5941 )
pyrrolizines (CHEBI:5941 )
Pyrrolizidine alkaloids (C10330 )

Ontology

No ontology term

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Not Available
Physical Description	Not Available
Mass Composition	Not Available
Melting Point	Not Available
Boiling Point	Not Available
Experimental Water Solubility	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	Not Available
Spectroscopic UV Data	Not Available
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Not Available

MS/MS

Type	Description	Splash Key	View
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0f89-0894000000-0ca28f402d6c3271b3a2	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00dv-5930000000-4468609a3d1860632eef	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-007a-7900000000-5a507c75289e1cb511d8	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00kb-1690000000-463ea0b40b7c8f9f7914	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-02aa-1960000000-f1389da2df24657ebf1e	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00xs-9500000000-374e4d150e4fd3eaa16f	2016-08-03	View Spectrum

NMR

Not Available

External Links

ChemSpider ID

Not Available

ChEMBL ID

Not Available

KEGG Compound ID

C10330

Pubchem Compound ID

114843

Pubchem Substance ID

Not Available

ChEBI ID

5941

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

Not Available

CRC / DFC (Dictionary of Food Compounds) ID

Not Available

EAFUS ID

Not Available

Dr. Duke ID

INTERMEDINE

BIGG ID

Not Available

KNApSAcK ID

C00002093

HET ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

Not Available

SuperScent ID

Not Available

Wikipedia ID

Not Available

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

Food	Content Range	Average	Reference
Food			Reference

Biological Effects and Interactions

Health Effects / Bioactivities

Descriptor	ID	Definition	Reference
hepatotoxic	50908	A role played by a chemical compound exihibiting itself through the ability to induce damage to the liver in animals.	DUKE

Enzymes

Not Available

Pathways

Not Available

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

Not Available

Files

MSDS

Not Available

References

Synthesis Reference

Not Available

General Reference

Not Available

Content Reference

— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).

Showing Compound Intermedine (FDB004288)

Structure for FDB004288 (Intermedine)