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

Details

• Internal ID: f22a12ac-9b59-4751-9837-a2279c8572b5
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Triterpenoids
• IUPAC Name: (5R,8R,9S,10R,13R,14R,17S)-17-[(2S)-2-hydroxy-6-methylhept-5-en-2-yl]-4,4,8,10,14-pentamethyl-1,2,5,6,7,9,11,12,13,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-one
• SMILES (Canonical): CC(=CCCC(C)(C1CCC2(C1CCC3C2(CCC4C3(CCC(=O)C4(C)C)C)C)C)O)C
• SMILES (Isomeric): CC(=CCC[C@@](C)([C@H]1CC[C@@]2([C@@H]1CC[C@@H]3[C@]2(CC[C@@H]4[C@@]3(CCC(=O)C4(C)C)C)C)C)O)C
• InChI: InChI=1S/C30H50O2/c1-20(2)10-9-16-30(8,32)22-13-18-28(6)21(22)11-12-24-27(5)17-15-25(31)26(3,4)23(27)14-19-29(24,28)7/h10,21-24,32H,9,11-19H2,1-8H3/t21-,22+,23+,24+,27+,28-,29-,30+/m1/s1
• InChI Key: NJICGAVMYWKCMW-HSUNHJJFSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₀H₅₀O₂
• Molecular Weight: 442.70 g/mol
• Exact Mass: 442.381080833 g/mol
• Topological Polar Surface Area (TPSA): 37.30 Ų
• XlogP: 8.20
• Atomic LogP (AlogP): 7.74
• H-Bond Acceptor: 2
• H-Bond Donor: 1
• Rotatable Bonds: 4

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	1.0000	100.00%
Caco-2	+	0.5286	52.86%
Blood Brain Barrier	+	0.5750	57.50%
Human oral bioavailability	-	0.6429	64.29%
Subcellular localzation	Mitochondria	0.7219	72.19%
OATP2B1 inhibitior	-	0.7203	72.03%
OATP1B1 inhibitior	+	0.8499	84.99%
OATP1B3 inhibitior	+	0.9394	93.94%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	+	0.5750	57.50%
BSEP inhibitior	+	0.9710	97.10%
P-glycoprotein inhibitior	-	0.5000	50.00%
P-glycoprotein substrate	-	0.8359	83.59%
CYP3A4 substrate	+	0.6471	64.71%
CYP2C9 substrate	-	0.8375	83.75%
CYP2D6 substrate	-	0.8168	81.68%
CYP3A4 inhibition	-	0.8359	83.59%
CYP2C9 inhibition	-	0.8869	88.69%
CYP2C19 inhibition	-	0.7734	77.34%
CYP2D6 inhibition	-	0.9597	95.97%
CYP1A2 inhibition	-	0.9266	92.66%
CYP2C8 inhibition	-	0.6567	65.67%
CYP inhibitory promiscuity	-	0.7134	71.34%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.5796	57.96%
Eye corrosion	-	0.9946	99.46%
Eye irritation	-	0.9297	92.97%
Skin irritation	+	0.6466	64.66%
Skin corrosion	-	0.9675	96.75%
Ames mutagenesis	-	0.6054	60.54%
Human Ether-a-go-go-Related Gene inhibition	-	0.4280	42.80%
Micronuclear	-	0.9700	97.00%
Hepatotoxicity	-	0.7223	72.23%
skin sensitisation	+	0.5678	56.78%
Respiratory toxicity	+	0.8333	83.33%
Reproductive toxicity	+	0.9778	97.78%
Mitochondrial toxicity	+	0.9500	95.00%
Nephrotoxicity	-	0.7314	73.14%
Acute Oral Toxicity (c)	III	0.8115	81.15%
Estrogen receptor binding	+	0.8123	81.23%
Androgen receptor binding	+	0.7264	72.64%
Thyroid receptor binding	+	0.7103	71.03%
Glucocorticoid receptor binding	+	0.8168	81.68%
Aromatase binding	+	0.7704	77.04%
PPAR gamma	+	0.6926	69.26%
Honey bee toxicity	-	0.7482	74.82%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	+	0.5800	58.00%
Fish aquatic toxicity	+	0.9885	98.85%

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	95.84%	91.11%
CHEMBL253	P34972	Cannabinoid CB2 receptor	95.52%	97.25%
CHEMBL1937	Q92769	Histone deacetylase 2	92.77%	94.75%
CHEMBL2581	P07339	Cathepsin D	92.55%	98.95%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	90.27%	94.45%
CHEMBL1994	P08235	Mineralocorticoid receptor	90.12%	100.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	88.27%	97.09%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	87.84%	96.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.72%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	84.90%	86.33%
CHEMBL5608	Q16288	NT-3 growth factor receptor	83.66%	95.89%
CHEMBL1902	P62942	FK506-binding protein 1A	82.68%	97.05%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	82.38%	89.34%
CHEMBL241	Q14432	Phosphodiesterase 3A	81.14%	92.94%

Plants that contains it

• Aldama oblongifolia
• Artemisia schimperi
• Cajanus trinervius
• Dipterocarpus hispidus
• Elephantopus mollis
• Euryops algoensis
• Gardenia jasminoides
• Gomortega keule
• Iris ensata
• Litsea pungens
• Nuphar lutea
• Petasites hybridus
• Phoenix loureiroi
• Picea mariana
• Quercus robur
• Salvia parryi
• Staphylea ternata
• Thalictrum longistylum
• Viburnum urceolatum
• Xyris pterygoblephara

Cross-Links

• PubChem: 12309262
• NPASS: NPC4467
• LOTUS: LTS0255771
• wikiData: Q105180147