Triptophenolide

Details

• Internal ID: bd7489cf-1284-4427-9095-2e63fa0caccf
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Oxosteroids
• IUPAC Name: (3bR,9bS)-6-hydroxy-9b-methyl-7-propan-2-yl-3,3b,4,5,10,11-hexahydronaphtho[2,1-e][2]benzofuran-1-one
• SMILES (Canonical): CC(C)C1=C(C2=C(C=C1)C3(CCC4=C(C3CC2)COC4=O)C)O
• SMILES (Isomeric): CC(C)C1=C(C2=C(C=C1)[C@]3(CCC4=C([C@@H]3CC2)COC4=O)C)O
• InChI: InChI=1S/C20H24O3/c1-11(2)12-4-6-16-14(18(12)21)5-7-17-15-10-23-19(22)13(15)8-9-20(16,17)3/h4,6,11,17,21H,5,7-10H2,1-3H3/t17-,20+/m0/s1
• InChI Key: KPXIBWGPZSPABK-FXAWDEMLSA-N
• Popularity: 18 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₂₄O₃
• Molecular Weight: 312.40 g/mol
• Exact Mass: 312.17254462 g/mol
• Topological Polar Surface Area (TPSA): 46.50 Ų
• XlogP: 4.00
• Atomic LogP (AlogP): 3.98
• H-Bond Acceptor: 3
• H-Bond Donor: 1
• Rotatable Bonds: 1

Synonyms

• 74285-86-2
• Tryptophenolide
• Hypolide
• (3bR,9bS)-6-hydroxy-9b-methyl-7-propan-2-yl-3,3b,4,5,10,11-hexahydronaphtho[2,1-e][2]benzofuran-1-one
• Phenanthro[1,2-c]furan-1(3H)-one,3b,4,5,9b,10,11-hexahydro-6-hydroxy-9b-methyl-7-(1-methylethyl)-,(3bR,9bS)-
• Hypolide;(+)-Triptophenolide
• Triptohenolide
• (-)-triptophenolide
• (+)-Triptophenolide
• Spectrum_001722
• SpecPlus_000566
• Spectrum2_001618
• Spectrum3_001928
• Spectrum4_001660
• Spectrum5_000539
• BSPBio_003528
• KBioGR_002159
• KBioSS_002202
• DivK1c_006662
• SPECTRUM1504005
• SPBio_001655
• CHEMBL3039217
• SCHEMBL19236270
• KBio1_001606
• KBio2_002202
• KBio2_004770
• KBio2_007338
• KBio3_002756
• DTXSID80995809
• CHEBI:114185
• BCP26008
• HY-N0475
• BDBM50199857
• CCG-38739
• MFCD00210567
• s9045
• AKOS015897179
• CS-3764
• SDCCGMLS-0066775.P001
• AC-34444
• MS-24563
• Phenanthro(1,2-c)furan-1(3H)-one, 3b,4,5,9b,10,11-hexahydro-6-hydroxy-9b-methyl-7-(1-methylethyl)-, (3bR-trans)-
• A838080
• SR-05000002569
• SR-05000002569-1
• BRD-K73210450-001-02-3
• BRD-K73210450-001-03-1
• Q27195253
• (3bR,9bS)-6-hydroxy-9b-methyl-7-propan-2-yl-3,3b,4,5,10,11-hexahydronaphtho[2,1-e]isobenzofuran-1-one
• 6-hydroxy-7-isopropyl-9b-methyl-3,3b,4,5,10,11-hexahydronaphtho[2,1-e]isobenzofuran-1-one
• 6-Hydroxy-9b-methyl-7-(propan-2-yl)-3b,4,5,9b,10,11-hexahydrophenanthro[1,2-c]furan-1(3H)-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	1.0000	100.00%
Caco-2	+	0.8724	87.24%
Blood Brain Barrier	+	0.6750	67.50%
Human oral bioavailability	-	0.6286	62.86%
Subcellular localzation	Mitochondria	0.8926	89.26%
OATP2B1 inhibitior	-	0.8600	86.00%
OATP1B1 inhibitior	+	0.9414	94.14%
OATP1B3 inhibitior	+	0.9479	94.79%
MATE1 inhibitior	-	0.8200	82.00%
OCT2 inhibitior	-	0.5000	50.00%
BSEP inhibitior	-	0.5000	50.00%
P-glycoprotein inhibitior	-	0.8093	80.93%
P-glycoprotein substrate	-	0.7019	70.19%
CYP3A4 substrate	+	0.6507	65.07%
CYP2C9 substrate	-	0.6108	61.08%
CYP2D6 substrate	-	0.8600	86.00%
CYP3A4 inhibition	+	0.6596	65.96%
CYP2C9 inhibition	+	0.6369	63.69%
CYP2C19 inhibition	+	0.7169	71.69%
CYP2D6 inhibition	-	0.7874	78.74%
CYP1A2 inhibition	+	0.8441	84.41%
CYP2C8 inhibition	-	0.7346	73.46%
CYP inhibitory promiscuity	+	0.5764	57.64%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9000	90.00%
Carcinogenicity (trinary)	Non-required	0.5466	54.66%
Eye corrosion	-	0.9916	99.16%
Eye irritation	-	0.8521	85.21%
Skin irritation	-	0.6853	68.53%
Skin corrosion	-	0.9498	94.98%
Ames mutagenesis	-	0.6400	64.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4284	42.84%
Micronuclear	-	0.8100	81.00%
Hepatotoxicity	+	0.9000	90.00%
skin sensitisation	-	0.7685	76.85%
Respiratory toxicity	+	0.8778	87.78%
Reproductive toxicity	+	0.8000	80.00%
Mitochondrial toxicity	+	0.6750	67.50%
Nephrotoxicity	-	0.8478	84.78%
Acute Oral Toxicity (c)	III	0.5657	56.57%
Estrogen receptor binding	-	0.4943	49.43%
Androgen receptor binding	+	0.6170	61.70%
Thyroid receptor binding	+	0.7428	74.28%
Glucocorticoid receptor binding	+	0.6452	64.52%
Aromatase binding	-	0.6632	66.32%
PPAR gamma	+	0.6402	64.02%
Honey bee toxicity	-	0.8330	83.30%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	-	0.6400	64.00%
Fish aquatic toxicity	+	1.0000	100.00%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1871	P10275	Androgen Receptor	260 nM	IC50	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	99.32%	91.11%
CHEMBL2581	P07339	Cathepsin D	96.19%	98.95%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	95.52%	94.45%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.09%	95.56%
CHEMBL1994	P08235	Mineralocorticoid receptor	91.02%	100.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	89.97%	96.09%
CHEMBL3359	P21462	Formyl peptide receptor 1	88.78%	93.56%
CHEMBL1806	P11388	DNA topoisomerase II alpha	87.90%	89.00%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	86.83%	93.40%
CHEMBL3137262	O60341	LSD1/CoREST complex	86.56%	97.09%
CHEMBL5608	Q16288	NT-3 growth factor receptor	85.35%	95.89%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	85.12%	99.15%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	84.36%	99.23%
CHEMBL253	P34972	Cannabinoid CB2 receptor	83.59%	97.25%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	83.47%	82.69%
CHEMBL2553	Q15418	Ribosomal protein S6 kinase alpha 1	82.68%	85.11%

Plants that contains it

• Cynanchum gracillimum
• Tripterygium doianum
• Tripterygium regelii
• Tripterygium wilfordii

Cross-Links

• PubChem: 173273
• NPASS: NPC131684
• ChEMBL: CHEMBL3039217
• LOTUS: LTS0181594
• wikiData: Q105372789