Celastrol

Details

• Internal ID: a8adee55-0600-4070-bde2-0ac12482f540
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Triterpenoids
• IUPAC Name: (2R,4aS,6aR,6aS,14aS,14bR)-10-hydroxy-2,4a,6a,6a,9,14a-hexamethyl-11-oxo-1,3,4,5,6,13,14,14b-octahydropicene-2-carboxylic acid
• SMILES (Canonical): CC1=C(C(=O)C=C2C1=CC=C3C2(CCC4(C3(CCC5(C4CC(CC5)(C)C(=O)O)C)C)C)C)O
• SMILES (Isomeric): CC1=C(C(=O)C=C2C1=CC=C3[C@]2(CC[C@@]4([C@@]3(CC[C@@]5([C@H]4C[C@](CC5)(C)C(=O)O)C)C)C)C)O
• InChI: 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
• Popularity: 1,548 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₉H₃₈O₄
• Molecular Weight: 450.60 g/mol
• Exact Mass: 450.27700969 g/mol
• Topological Polar Surface Area (TPSA): 74.60 Ų
• XlogP: 5.90
• Atomic LogP (AlogP): 6.70
• H-Bond Acceptor: 3
• H-Bond Donor: 2
• Rotatable Bonds: 1

Synonyms

• 34157-83-0
• Tripterin
• Tripterine
• (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
• Celastrol, Celastrus scandens
• C29H38O4
• NSC70931
• NSC 70931
• (2R,4aS,6aR,6aS,14aS,14bR)-10-hydroxy-2,4a,6a,6a,9,14a-hexamethyl-11-oxo-1,3,4,5,6,13,14,14b-octahydropicene-2-carboxylic acid
• UNII-L8GG98663L
• CHEBI:63959
• 34157-83-0 (castrol)
• L8GG98663L
• NSC-70931
• D:A-Friedo-24-noroleana-1(10),3,5,7-tetraen-29-oic acid, 3-hydroxy-2-oxo-, (20alpha)-
• 24,25,26-Trinoroleana-1(10),3,5,7-tetraen-29-oic acid,3-hydroxy-9,13-dimethyl-2-oxo-, (9b,13a,14b,20a)-
• 3-hydroxy-9beta,13alpha-dimethyl-2-oxo-24,25,26-trinoroleana-1(10),3,5,7-tetraen-29-oic acid
• SR-05000002679
• MLS002701906
• 3-Hydroxy-24-nor-2-oxo-1(10),3,5,7-friedelatetraen-29-oic Acid
• MFCD03424073
• Spectrum_000335
• CELASTROL [MI]
• Spectrum2_000150
• Spectrum3_000233
• Spectrum4_001966
• Spectrum5_000805
• D0I9XH
• C12H16NS.Br
• SCHEMBL14954
• BSPBio_001905
• KBioGR_002436
• KBioSS_000815
• SPECTRUM201664
• MLS006011086
• DivK1c_000718
• SPBio_000260
• 11-alpha-hydroxyandrostenedione
• C12-H16-N-S.Br
• DTXSID2040993
• GTPL10386
• KBio1_000718
• KBio2_000815
• KBio2_003383
• KBio2_005951
• KBio3_001405
• KQJSQWZMSAGSHN-JJWQIEBTSA-N
• NINDS_000718
• BDBM205457
• HMS1923A13
• HMS3649E12
• HMS3884G09
• 10-hydroxy-2,4a,6a,6a,9,14a-hexamethyl-11-oxo-1,3,4,5,6,13,14,14b-octahydropicene-2-carboxylic acid
• BCP07973
• EX-A7823
• CCG-39919
• HB4605
• s1290
• Celastrol, >=98% (HPLC), solid
• AKOS025311497
• AC-6031
• compound 2 [PMID: 28621943]
• CS-0409
• GS-6082
• IDI1_000718
• NCGC00178913-01
• NCGC00178913-02
• NCGC00178913-04
• NCGC00178913-05
• NCGC00178913-14
• HY-13067
• NCI60_038570
• SMR004702874
• LS-157465
• C2737
• H10498
• A822102
• Q-100413
• Q5057534
• SR-05000002679-1
• SR-05000002679-3
• SR-05000002679-4
• (20alpha)-3-hydroxy-2-oxo-D:A-Friedo-24-noroleana-1(10),3,5,7-tetraen-29-oate
• (20alpha)-3-hydroxy-2-oxo-D:A-Friedo-24-noroleana-1(10),3,5,7-tetraen-29-oic acid
• 24-NOR-D:A-FRIEDOOLEANA-1(10),3,5,7-TETRAEN-29-OIC ACID, 3-HYDROXY-2-OXO-
• (2R,4aS,6aR,6aS,14aS,14bR)-10-hydroxy-2,4a,6a,6a,9,14a-hexamethyl-11-oxo-1,3,4,5,6,13,14,14b-octahydropicene-2-carboxylicacid
• (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
• (9-beta,13-alpha,14-beta,20-alpha)-3-Hydroxy-9,13-dimethyl-2-oxo-24,25,26-trinoroleana-1(10),3,5,7-tetraen-29-oic acid
• (9?,13?,14?,20?)-3-Hydroxy-9,13-dimethyl-2-oxo-24,25,26-trinoroleana-1(10),3,5,7-tetraen-29-oic acid
• 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
• 2-Picenecarboxylic acid, 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-, (2R,4aS,6aS,12bR,14aS,14bR)-
• 2-Picenecarboxylic acid,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-
• 24,25,26-TRINOROLEANA-1(10),3,5,7-TETRAEN-29-OIC ACID, 3-HYDROXY-9,13-DIMETHYL-2-OXO-, (9.BETA.,13.ALPHA.,14.BETA.,20.ALPHA.)-
• 3-Hydroxy-9.beta.,13.alpha.-dimethyl-2-oxo-24,25,26-trinoroleana-1(10),3,5,7-tetraen-29-oic acid

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9867	98.67%
Caco-2	+	0.5093	50.93%
Blood Brain Barrier	+	0.6500	65.00%
Human oral bioavailability	-	0.5000	50.00%
Subcellular localzation	Mitochondria	0.8627	86.27%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9414	94.14%
OATP1B3 inhibitior	-	0.3619	36.19%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.5092	50.92%
BSEP inhibitior	+	0.9408	94.08%
P-glycoprotein inhibitior	-	0.4738	47.38%
P-glycoprotein substrate	-	0.6151	61.51%
CYP3A4 substrate	+	0.6425	64.25%
CYP2C9 substrate	-	0.7739	77.39%
CYP2D6 substrate	-	0.9120	91.20%
CYP3A4 inhibition	-	0.8401	84.01%
CYP2C9 inhibition	-	0.8821	88.21%
CYP2C19 inhibition	-	0.9302	93.02%
CYP2D6 inhibition	-	0.9206	92.06%
CYP1A2 inhibition	-	0.7552	75.52%
CYP2C8 inhibition	+	0.4780	47.80%
CYP inhibitory promiscuity	-	0.9376	93.76%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.6304	63.04%
Eye corrosion	-	0.9931	99.31%
Eye irritation	-	0.9356	93.56%
Skin irritation	+	0.6275	62.75%
Skin corrosion	-	0.9558	95.58%
Ames mutagenesis	-	0.5400	54.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7765	77.65%
Micronuclear	-	0.7500	75.00%
Hepatotoxicity	-	0.5245	52.45%
skin sensitisation	-	0.5440	54.40%
Respiratory toxicity	+	0.5444	54.44%
Reproductive toxicity	+	0.8444	84.44%
Mitochondrial toxicity	+	0.7625	76.25%
Nephrotoxicity	+	0.5167	51.67%
Acute Oral Toxicity (c)	III	0.5253	52.53%
Estrogen receptor binding	+	0.8134	81.34%
Androgen receptor binding	+	0.7548	75.48%
Thyroid receptor binding	+	0.7615	76.15%
Glucocorticoid receptor binding	+	0.7859	78.59%
Aromatase binding	+	0.8239	82.39%
PPAR gamma	+	0.7171	71.71%
Honey bee toxicity	-	0.8401	84.01%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.7234	72.34%
Fish aquatic toxicity	+	1.0000	100.00%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL5869	Q00613	Heat shock factor protein 1	2600 nM; 1100 nM	EC50; EC50	PMID: 19502057; PMID: 19502057
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	13200 nM	IC50	PMID: 21193311
CHEMBL3166	P29350	Protein-tyrosine phosphatase 1C	27800 nM	IC50	PMID: 21193311
CHEMBL3864	Q06124	Protein-tyrosine phosphatase 2C	3300 nM	IC50	PMID: 21193311
CHEMBL2916	O14746	Telomerase reverse transcriptase	780 nM; 780 nM	IC50; IC50	via Super-PRED; PMID: 25812966

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3746	P80365	11-beta-hydroxysteroid dehydrogenase 2	94.81%	94.78%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	94.41%	94.45%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	92.61%	99.23%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	92.51%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.46%	95.56%
CHEMBL279	P35968	Vascular endothelial growth factor receptor 2	89.30%	95.52%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	83.67%	96.09%
CHEMBL2581	P07339	Cathepsin D	82.91%	98.95%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	80.74%	93.03%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	80.37%	93.00%

Plants that contains it

• Berberis lambertii
• Catha edulis
• Celastrus hypoleucus
• Celastrus orbiculatus
• Celastrus paniculatus
• Centella asiatica
• Crossopetalum gaumeri
• Echinochloa crus-galli
• Gymnosporia cassinoides
• Kokoona ochracea
• Kokoona zeylanica
• Maytenus chubutensis
• Maytenus woodsonii
• Orthosphenia mexicana
• Peritassa campestris
• Reissantia buchananii
• Salacia kraussii
• Salacia reticulata
• Semialarium mexicanum
• Taraxacum coreanum
• Taraxacum mongolicum
• Taraxacum officinale
• Taraxacum platycarpum
• Taraxacum sinicum
• Thunbergia grandiflora
• Tripterygium regelii
• Tripterygium wilfordii
• Zanthoxylum syncarpum

Cross-Links

• PubChem: 122724
• NPASS: NPC112454
• ChEMBL: CHEMBL301982
• LOTUS: LTS0029200
• wikiData: Q5057534