Bovine Metabolome Database: Showing metabocard for Celastrol (BMDB0002385)

Identification Taxonomy Physical properties Pathways Spectra Concentrations Links References enzymes (1) Show 1 protein XML

Record Information

Version

1.0

Creation Date

2016-09-30 22:54:54 UTC

Update Date

2020-04-22 15:10:53 UTC

BMDB ID

BMDB0002385

Secondary Accession Numbers

BMDB02385

Metabolite Identification

Common Name

Celastrol

Description

Celastrol, also known as tripterine, belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units. Based on a literature review a significant number of articles have been published on Celastrol.

Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Value	Source
(2R,4AS,6as,12BR,14as,14BR)-1,2,3,4,4a,5,6,6a,11,12b,13,14,14a,14b-tetradecahydro-10-hydroxy-2,4a,6a,9,12b,14a-hexamethyl-11-oxo-2-picenecarboxylic acid	ChEBI
3-Hydroxy-9beta,13alpha-dimethyl-2-oxo-24,25,26-trinoroleana-1(10),3,5,7-tetraen-29-Oic acid	ChEBI
Tripterine	ChEBI
(2R,4AS,6as,12BR,14as,14BR)-1,2,3,4,4a,5,6,6a,11,12b,13,14,14a,14b-tetradecahydro-10-hydroxy-2,4a,6a,9,12b,14a-hexamethyl-11-oxo-2-picenecarboxylate	Generator
3-Hydroxy-9b,13a-dimethyl-2-oxo-24,25,26-trinoroleana-1(10),3,5,7-tetraen-29-Oate	Generator
3-Hydroxy-9b,13a-dimethyl-2-oxo-24,25,26-trinoroleana-1(10),3,5,7-tetraen-29-Oic acid	Generator
3-Hydroxy-9beta,13alpha-dimethyl-2-oxo-24,25,26-trinoroleana-1(10),3,5,7-tetraen-29-Oate	Generator
3-Hydroxy-9β,13α-dimethyl-2-oxo-24,25,26-trinoroleana-1(10),3,5,7-tetraen-29-Oate	Generator
3-Hydroxy-9β,13α-dimethyl-2-oxo-24,25,26-trinoroleana-1(10),3,5,7-tetraen-29-Oic acid	Generator
3-Hydroxy-24-nor-2-oxo-1(10),3,5,7-friedelatetraen-29-Oic acid	MeSH
Tripterin	MeSH
(20alpha)-3-Hydroxy-2-oxo-d:a-friedo-24-noroleana-1(10),3,5,7-tetraen-29-Oate	HMDB
(20alpha)-3-Hydroxy-2-oxo-d:a-friedo-24-noroleana-1(10),3,5,7-tetraen-29-Oic acid	HMDB
1,2,3,4,4a,5,6,6a, 11,12b,13,14,14a,14b-tetradecahydro-10-Hydroxy-2,4a,6a,9,12b, 14a-hexamethyl-11-oxo-2-picenecarboxylic acid	HMDB

Chemical Formula

C₂₉H₃₈O₄

Average Molecular Weight

450.6096

Monoisotopic Molecular Weight

450.277009704

IUPAC Name

(2R,4aS,6aS,12bR,14aS,14bR)-10-hydroxy-2,4a,6a,9,12b,14a-hexamethyl-11-oxo-1,2,3,4,4a,5,6,6a,11,12b,13,14,14a,14b-tetradecahydropicene-2-carboxylic acid

Traditional Name

triterpene

CAS Registry Number

34157-83-0

SMILES

[H][C@@]12C[C@@](C)(CC[C@]1(C)CC[C@]1(C)C3=CC=C4C(C)=C(O)C(=O)C=C4[C@]3(C)CC[C@@]21C)C(O)=O

InChI Identifier

InChI=1S/C29H38O4/c1-17-18-7-8-21-27(4,19(18)15-20(30)23(17)31)12-14-29(6)22-16-26(3,24(32)33)10-9-25(22,2)11-13-28(21,29)5/h7-8,15,22,31H,9-14,16H2,1-6H3,(H,32,33)/t22-,25-,26-,27+,28-,29+/m1/s1

InChI Key

KQJSQWZMSAGSHN-JJWQIEBTSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Triterpenoids

Direct Parent

Triterpenoids

Alternative Parents

Substituents

Triterpenoid
Cyclic ketone
Ketone
Monocarboxylic acid or derivatives
Enol
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

monocarboxylic acid (CHEBI:63959 )
pentacyclic triterpenoid (CHEBI:63959 )

Ontology

Status

Expected but not Quantified

Origin

Endogenous

Exogenous

Biofunction

Not Available

Application

Not Available

Cellular locations

Cell membrane
Cytoplasm
Membrane

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	6.1	ALOGPS
logP	5.33	ChemAxon
logS	-5.3	ALOGPS
pKa (Strongest Acidic)	4.78	ChemAxon
pKa (Strongest Basic)	-3.5	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	74.6 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	132.75 m³·mol⁻¹	ChemAxon
Polarizability	51.31 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0079-0014900000-6314885dda7c42ed3d1c	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive	splash10-004i-0010290000-9d6a734ac76d3675e1d1	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	View in JSpectraViewer
LC-MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , negative	splash10-0btc-0019500000-1c1a5c4d90edabb683a8	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , positive	splash10-0udi-0090200000-a5a5d86168a13b1cebb9	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , positive	splash10-05fr-0090500000-52142edc10fd3d8f32c6	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , positive	splash10-002u-0090200000-1c928670757fc3cd1d3c	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-0udi-0090000000-2df6f0faeb5a9cecc2eb	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-0udi-0090400000-927f3c53625e81d33fae	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-0udi-0090000000-e92220b1115c5f023e57	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0f89-0000900000-d815c343de2be89e8896	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a59-0113900000-2fe25b729286a0d53dc6	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-01p2-1019300000-80c6a400d2828b2c1a4b	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0002-0000900000-ad4c64962161c1430e94	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4j-0000900000-a921248ee3c46bc344ac	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0019-1009800000-7e240152d07e38bf3e4d	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0udi-0010900000-876bac071b1bf2fe4a42	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0k92-0131900000-7d50983e3b91735ea144	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0w29-0594000000-cb3ee89de6bdda2853a3	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-052b-0000900000-82473f6edf6524bbadc6	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0002-0000900000-6611061fcf5a016d150a	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-052k-4006900000-16ba59a651d5e61c6798	View in MoNA

Biological Properties

Cellular Locations

Cell membrane
Cytoplasm
Membrane

Biospecimen Locations

Not Available

Pathways

Not Available

Name	SMPDB/Pathwhiz	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

External Links

HMDB ID

HMDB0002385

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022989

KNApSAcK ID

C00029919

Chemspider ID

109405

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Celastrol

METLIN ID

Not Available

PubChem Compound

122724

PDB ID

Not Available

ChEBI ID

63959

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Enzymes

Enzyme Details

1. Calcium-activated potassium channel subunit beta-1

General function:: Involved in potassium ion transport
Specific function:: Regulatory subunit of the calcium activated potassium KCNMA1 (maxiK) channel. Modulates the calcium sensitivity and gating kinetics of KCNMA1, thereby contributing to KCNMA1 channel diversity. Increases the apparent Ca(2+)/voltage sensitivity of the KCNMA1 channel. It also modifies KCNMA1 channel kinetics and alters its pharmacological properties. It slows down the activation and the deactivation kinetics of the channel. Acts as a negative regulator of smooth muscle contraction by enhancing the calcium sensitivity to KCNMA1. Its presence is also a requirement for internal binding of the KCNMA1 channel opener dehydrosoyasaponin I (DHS-1) triterpene glycoside and for external binding of the agonist hormone 17-beta-estradiol (E2). Increases the binding activity of charybdotoxin (CTX) toxin to KCNMA1 peptide blocker by increasing the CTX association rate and decreasing the dissociation rate (By similarity).
Gene Name:: KCNMB1
Uniprot ID:: Q28067
Molecular weight:: 21957.0

Showing metabocard for Celastrol (BMDB0002385)

Structure for BMDB0002385 (Celastrol)

Enzymes