5-(3,17-Dihydroxy-4,4,8,10,14-pentamethyl-1,2,3,5,6,7,9,11,12,13,15,16-dodecahydrocyclopenta[a]phenanthren-17-yl)-5-methyloxolan-2-one

Details

• Internal ID: 27a25f35-116a-48d1-86a0-345d8a144451
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Triterpenoids
• IUPAC Name: 5-(3,17-dihydroxy-4,4,8,10,14-pentamethyl-1,2,3,5,6,7,9,11,12,13,15,16-dodecahydrocyclopenta[a]phenanthren-17-yl)-5-methyloxolan-2-one
• SMILES (Canonical): CC1(C2CCC3(C(C2(CCC1O)C)CCC4C3(CCC4(C5(CCC(=O)O5)C)O)C)C)C
• SMILES (Isomeric): CC1(C2CCC3(C(C2(CCC1O)C)CCC4C3(CCC4(C5(CCC(=O)O5)C)O)C)C)C
• InChI: InChI=1S/C27H44O4/c1-22(2)17-9-13-24(4)18(23(17,3)12-10-20(22)28)7-8-19-25(24,5)15-16-27(19,30)26(6)14-11-21(29)31-26/h17-20,28,30H,7-16H2,1-6H3
• InChI Key: SAHJNWSRUWGRMS-UHFFFAOYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₇H₄₄O₄
• Molecular Weight: 432.60 g/mol
• Exact Mass: 432.32395988 g/mol
• Topological Polar Surface Area (TPSA): 66.80 Ų
• XlogP: 5.40
• Atomic LogP (AlogP): 5.24
• H-Bond Acceptor: 4
• H-Bond Donor: 2
• Rotatable Bonds: 1

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9860	98.60%
Caco-2	-	0.5479	54.79%
Blood Brain Barrier	-	0.6500	65.00%
Human oral bioavailability	+	0.5857	58.57%
Subcellular localzation	Mitochondria	0.8048	80.48%
OATP2B1 inhibitior	-	0.7106	71.06%
OATP1B1 inhibitior	+	0.9293	92.93%
OATP1B3 inhibitior	+	0.8869	88.69%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.7108	71.08%
BSEP inhibitior	+	0.7883	78.83%
P-glycoprotein inhibitior	-	0.7506	75.06%
P-glycoprotein substrate	-	0.8843	88.43%
CYP3A4 substrate	+	0.6715	67.15%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8422	84.22%
CYP3A4 inhibition	-	0.6155	61.55%
CYP2C9 inhibition	-	0.8725	87.25%
CYP2C19 inhibition	-	0.8246	82.46%
CYP2D6 inhibition	-	0.9583	95.83%
CYP1A2 inhibition	-	0.8209	82.09%
CYP2C8 inhibition	-	0.7780	77.80%
CYP inhibitory promiscuity	-	0.9441	94.41%
UGT catelyzed	-	0.7000	70.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6066	60.66%
Eye corrosion	-	0.9917	99.17%
Eye irritation	-	0.9046	90.46%
Skin irritation	+	0.5232	52.32%
Skin corrosion	-	0.9018	90.18%
Ames mutagenesis	-	0.7500	75.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5899	58.99%
Micronuclear	-	0.8900	89.00%
Hepatotoxicity	-	0.7716	77.16%
skin sensitisation	-	0.8451	84.51%
Respiratory toxicity	+	0.7667	76.67%
Reproductive toxicity	+	0.8222	82.22%
Mitochondrial toxicity	+	0.9000	90.00%
Nephrotoxicity	-	0.6148	61.48%
Acute Oral Toxicity (c)	III	0.5258	52.58%
Estrogen receptor binding	+	0.6974	69.74%
Androgen receptor binding	+	0.6555	65.55%
Thyroid receptor binding	+	0.5814	58.14%
Glucocorticoid receptor binding	+	0.7940	79.40%
Aromatase binding	+	0.7997	79.97%
PPAR gamma	+	0.5427	54.27%
Honey bee toxicity	-	0.8211	82.11%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	+	0.5200	52.00%
Fish aquatic toxicity	+	0.9789	97.89%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	91.58%	91.11%
CHEMBL2581	P07339	Cathepsin D	89.85%	98.95%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	89.29%	94.45%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.28%	95.56%
CHEMBL1994	P08235	Mineralocorticoid receptor	87.01%	100.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	85.59%	95.89%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	84.72%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	84.42%	97.09%
CHEMBL253	P34972	Cannabinoid CB2 receptor	83.55%	97.25%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	81.43%	82.69%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	80.24%	96.38%

Plants that contains it

• Cleome africana

Cross-Links

• PubChem: 85162653
• LOTUS: LTS0200275
• wikiData: Q105248861