ContaminantDB: Levcromakalim

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-05-22 05:16:52 UTC

Update Date

2026-04-15 17:50:21 UTC

Accession Number

CHEM018483

Identification

Common Name

Levcromakalim

Class

Small Molecule

Description

Cromakalim (INN) is a potassium channel-opening vasodilator. The active isomer is levcromakalim. It acts on ATP-sensitive potassium channels and so causes membrane hyperpolarization. It can be used to treat hypertension as it will relax vascular smooth muscle to lower blood pressure. Hyperpolarisation of smooth muscle cell membranes pulls their membrane potential away from the threshold, so making it more difficult to excite them and thereby cause relaxation.

Contaminant Sources

ToxCast & Tox21 Chemicals

Contaminant Type

Not Available

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(-)-Cromakalim	Kegg
Lemakalim	Kegg
Cromakalim, (3S-cis)-isomer	MeSH
Cromakalim, (3R-cis)-isomer	MeSH
Cromakalim, (3R-trans)-isomer	MeSH
Cromakalim, (trans)-isomer	MeSH
Cromakalim	MeSH
Cromakalim, (3S-trans)-isomer	MeSH

Chemical Formula

C₁₆H₁₈N₂O₃

Average Molecular Mass

286.331 g/mol

Monoisotopic Mass

286.132 g/mol

CAS Registry Number

94535-50-9

IUPAC Name

(3S,4R)-3-hydroxy-2,2-dimethyl-4-(2-oxopyrrolidin-1-yl)-3,4-dihydro-2H-1-benzopyran-6-carbonitrile

Traditional Name

(-)-cromakalim

SMILES

[H][C@]1(O)[C@]([H])(N2CCCC2=O)C2=C(OC1(C)C)C=CC(=C2)C#N

InChI Identifier

InChI=1S/C16H18N2O3/c1-16(2)15(20)14(18-7-3-4-13(18)19)11-8-10(9-17)5-6-12(11)21-16/h5-6,8,14-15,20H,3-4,7H2,1-2H3/t14-,15+/m1/s1

InChI Key

TVZCRIROJQEVOT-CABCVRRESA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as 2,2-dimethyl-1-benzopyrans. These are organic compounds containing a 1-benzopyran moiety that carries two methyl groups at the 2-position.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzopyrans

Sub Class

1-benzopyrans

Direct Parent

2,2-dimethyl-1-benzopyrans

Alternative Parents

Substituents

2,2-dimethyl-1-benzopyran
Alkyl aryl ether
Pyrrolidone
2-pyrrolidone
N-alkylpyrrolidine
Benzenoid
Pyrrolidine
Tertiary carboxylic acid amide
Carboxamide group
Lactam
Secondary alcohol
Oxacycle
Azacycle
Carboxylic acid derivative
Ether
Carbonitrile
Nitrile
Hydrocarbon derivative
Organic oxide
Carbonyl group
Organopnictogen compound
Organonitrogen compound
Organooxygen compound
Organic oxygen compound
Alcohol
Organic nitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

1-benzopyran (CHEBI:6436 )

Biological Properties

Status

Detected and Not Quantified

Origin

Not Available

Cellular Locations

Not Available

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Not Available

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	2.26 g/L	ALOGPS
logP	1.42	ALOGPS
logP	1.02	ChemAxon
logS	-2.1	ALOGPS
pKa (Strongest Acidic)	13.26	ChemAxon
pKa (Strongest Basic)	-1.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	73.56 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	76.67 m³·mol⁻¹	ChemAxon
Polarizability	30.12 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-0090000000-286d3b291c7937e1441e	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-014r-2290000000-ec019c1ce1860e1878f7	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-001j-1920000000-653fd52c87db3740aa88	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-1090000000-9eb53fc8a8b3066084ae	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000i-4190000000-78470ef73671ae30c6e7	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-067i-4900000000-ca4cdb2831c3f63d868a	Spectrum

Toxicity Profile

Route of Exposure

Not Available

Mechanism of Toxicity

Not Available

Metabolism

Not Available

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

Not Available

Uses/Sources

Not Available

Minimum Risk Level

Not Available

Health Effects

Not Available

Symptoms

Not Available

Treatment

Not Available

Concentrations

Not Available

External Links

DrugBank ID

Not Available

HMDB ID

Not Available

FooDB ID

Not Available

Phenol Explorer ID

Not Available

KNApSAcK ID

Not Available

BiGG ID

Not Available

BioCyc ID

Not Available

METLIN ID

Not Available

PDB ID

Not Available

Wikipedia Link

Cromakalim

Chemspider ID

Not Available

ChEBI ID

Not Available

PubChem Compound ID

93504

Kegg Compound ID

C11697

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Not Available

MSDS

Not Available

General References

Not Available

Levcromakalim (CHEM018483)

Structure for CHEM018483: Levcromakalim