(1S,3aS,5aS,5bR,7aR,9S,11aR,11bR,13bR)-9-hydroxy-5a,5b,8,8,11a-pentamethyl-1-propan-2-yl-1,2,3,4,5,6,7,7a,9,10,11,11b,12,13b-tetradecahydrocyclopenta[a]chrysene-3a-carboxylic acid

Details

• Internal ID: 7f8a5a1e-5234-494a-9737-369c8292c720
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Triterpenoids
• IUPAC Name: (1S,3aS,5aS,5bR,7aR,9S,11aR,11bR,13bR)-9-hydroxy-5a,5b,8,8,11a-pentamethyl-1-propan-2-yl-1,2,3,4,5,6,7,7a,9,10,11,11b,12,13b-tetradecahydrocyclopenta[a]chrysene-3a-carboxylic acid
• SMILES (Canonical): CC(C)C1CCC2(C1C3=CCC4C5(CCC(C(C5CCC4(C3(CC2)C)C)(C)C)O)C)C(=O)O
• SMILES (Isomeric): CC(C)[C@@H]1CC[C@]2([C@H]1C3=CC[C@@H]4[C@]5(CC[C@@H](C([C@@H]5CC[C@]4([C@@]3(CC2)C)C)(C)C)O)C)C(=O)O
• InChI: InChI=1S/C30H48O3/c1-18(2)19-10-15-30(25(32)33)17-16-28(6)20(24(19)30)8-9-22-27(5)13-12-23(31)26(3,4)21(27)11-14-29(22,28)7/h8,18-19,21-24,31H,9-17H2,1-7H3,(H,32,33)/t19-,21-,22+,23-,24+,27-,28+,29+,30-/m0/s1
• InChI Key: KOQBBUWNLZFEMV-SXDGTAOVSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₃₀H₄₈O₃
• Molecular Weight: 456.70 g/mol
• Exact Mass: 456.36034539 g/mol
• Topological Polar Surface Area (TPSA): 57.50 Ų
• XlogP: 7.30
• Atomic LogP (AlogP): 7.09
• H-Bond Acceptor: 2
• H-Bond Donor: 2
• Rotatable Bonds: 2

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	+	0.5446	54.46%
Blood Brain Barrier	-	0.6000	60.00%
Human oral bioavailability	-	0.5000	50.00%
Subcellular localzation	Mitochondria	0.8540	85.40%
OATP2B1 inhibitior	-	0.7165	71.65%
OATP1B1 inhibitior	+	0.9238	92.38%
OATP1B3 inhibitior	+	0.9086	90.86%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	+	0.6750	67.50%
BSEP inhibitior	+	0.8240	82.40%
P-glycoprotein inhibitior	-	0.9121	91.21%
P-glycoprotein substrate	-	0.8094	80.94%
CYP3A4 substrate	+	0.6490	64.90%
CYP2C9 substrate	-	0.8404	84.04%
CYP2D6 substrate	-	0.8509	85.09%
CYP3A4 inhibition	-	0.9088	90.88%
CYP2C9 inhibition	-	0.9189	91.89%
CYP2C19 inhibition	-	0.9182	91.82%
CYP2D6 inhibition	-	0.9537	95.37%
CYP1A2 inhibition	-	0.9191	91.91%
CYP2C8 inhibition	-	0.6533	65.33%
CYP inhibitory promiscuity	-	0.8698	86.98%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.5573	55.73%
Eye corrosion	-	0.9957	99.57%
Eye irritation	-	0.9212	92.12%
Skin irritation	+	0.7045	70.45%
Skin corrosion	-	0.9592	95.92%
Ames mutagenesis	-	0.8800	88.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5686	56.86%
Micronuclear	-	0.8400	84.00%
Hepatotoxicity	-	0.5188	51.88%
skin sensitisation	-	0.5291	52.91%
Respiratory toxicity	+	0.6111	61.11%
Reproductive toxicity	+	0.9778	97.78%
Mitochondrial toxicity	+	1.0000	100.00%
Nephrotoxicity	-	0.8307	83.07%
Acute Oral Toxicity (c)	III	0.6932	69.32%
Estrogen receptor binding	+	0.7440	74.40%
Androgen receptor binding	+	0.7360	73.60%
Thyroid receptor binding	+	0.6697	66.97%
Glucocorticoid receptor binding	+	0.8508	85.08%
Aromatase binding	+	0.6499	64.99%
PPAR gamma	+	0.5938	59.38%
Honey bee toxicity	-	0.8608	86.08%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.6200	62.00%
Fish aquatic toxicity	+	0.9959	99.59%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	92.90%	96.09%
CHEMBL2581	P07339	Cathepsin D	90.64%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.15%	95.56%
CHEMBL221	P23219	Cyclooxygenase-1	89.08%	90.17%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	88.71%	94.45%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	87.97%	91.11%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	86.86%	90.71%
CHEMBL3137262	O60341	LSD1/CoREST complex	85.94%	97.09%
CHEMBL340	P08684	Cytochrome P450 3A4	84.79%	91.19%
CHEMBL3359	P21462	Formyl peptide receptor 1	83.38%	93.56%
CHEMBL1994	P08235	Mineralocorticoid receptor	82.11%	100.00%
CHEMBL4227	P25090	Lipoxin A4 receptor	81.90%	100.00%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	81.80%	93.00%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	81.78%	93.03%
CHEMBL5608	Q16288	NT-3 growth factor receptor	81.31%	95.89%
CHEMBL2514	O95665	Neurotensin receptor 2	80.75%	100.00%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	80.62%	82.69%
CHEMBL5028	O14672	ADAM10	80.05%	97.50%

Plants that contains it

• Achillea arabica
• Argyranthemum frutescens
• Dryopteris crassirhizoma
• Euphorbia polygonifolia
• Hakea amplexicaulis
• Hyptis suaveolens
• Meliosma lanceolata
• Swertia petiolata
• Syzygium grande

Cross-Links

• PubChem: 13996060
• NPASS: NPC211235
• LOTUS: LTS0006110
• wikiData: Q105143935