(1S,3R,4R,7R,9S,10S,13R,15S)-5,5,9-trimethyl-14-methylidenetetracyclo[11.2.1.01,10.04,9]hexadecane-3,7,15-triol

Details

• Internal ID: 222c11a8-8e5c-4c02-a59d-b86570395cf9
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Diterpenoids > Kaurane diterpenoids
• IUPAC Name: (1S,3R,4R,7R,9S,10S,13R,15S)-5,5,9-trimethyl-14-methylidenetetracyclo[11.2.1.01,10.04,9]hexadecane-3,7,15-triol
• SMILES (Canonical): CC1(CC(CC2(C1C(CC34C2CCC(C3)C(=C)C4O)O)C)O)C
• SMILES (Isomeric): C[C@@]12C[C@@H](CC([C@H]1[C@@H](C[C@]34[C@H]2CC[C@H](C3)C(=C)[C@@H]4O)O)(C)C)O
• InChI: InChI=1S/C20H32O3/c1-11-12-5-6-15-19(4)9-13(21)8-18(2,3)16(19)14(22)10-20(15,7-12)17(11)23/h12-17,21-23H,1,5-10H2,2-4H3/t12-,13-,14-,15+,16-,17+,19+,20+/m1/s1
• InChI Key: OUDUFOYDAUOXPD-ZKKYUWNRSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₃₂O₃
• Molecular Weight: 320.50 g/mol
• Exact Mass: 320.23514488 g/mol
• Topological Polar Surface Area (TPSA): 60.70 Ų
• XlogP: 2.70
• Atomic LogP (AlogP): 2.89
• H-Bond Acceptor: 3
• H-Bond Donor: 3
• Rotatable Bonds: 0

Synonyms

• CHEMBL4098857
• 2,6,15-(-)-Kaur-16-ene
• AKOS032962304
• 2,6,15-Trihydroxy-ent-kaur-16-ene

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9960	99.60%
Caco-2	-	0.5124	51.24%
Blood Brain Barrier	-	0.5000	50.00%
Human oral bioavailability	+	0.7143	71.43%
Subcellular localzation	Mitochondria	0.5320	53.20%
OATP2B1 inhibitior	-	0.8545	85.45%
OATP1B1 inhibitior	+	0.8974	89.74%
OATP1B3 inhibitior	-	0.2198	21.98%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.6000	60.00%
BSEP inhibitior	-	0.8119	81.19%
P-glycoprotein inhibitior	-	0.8751	87.51%
P-glycoprotein substrate	-	0.7363	73.63%
CYP3A4 substrate	+	0.5836	58.36%
CYP2C9 substrate	-	0.6077	60.77%
CYP2D6 substrate	-	0.7196	71.96%
CYP3A4 inhibition	-	0.8125	81.25%
CYP2C9 inhibition	-	0.8348	83.48%
CYP2C19 inhibition	-	0.8324	83.24%
CYP2D6 inhibition	-	0.9455	94.55%
CYP1A2 inhibition	-	0.8616	86.16%
CYP2C8 inhibition	-	0.7269	72.69%
CYP inhibitory promiscuity	-	0.7682	76.82%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9000	90.00%
Carcinogenicity (trinary)	Non-required	0.6014	60.14%
Eye corrosion	-	0.9922	99.22%
Eye irritation	-	0.8635	86.35%
Skin irritation	+	0.5504	55.04%
Skin corrosion	-	0.9483	94.83%
Ames mutagenesis	-	0.6400	64.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5762	57.62%
Micronuclear	-	0.9400	94.00%
Hepatotoxicity	+	0.5250	52.50%
skin sensitisation	-	0.5284	52.84%
Respiratory toxicity	-	0.5333	53.33%
Reproductive toxicity	+	0.9556	95.56%
Mitochondrial toxicity	+	0.9875	98.75%
Nephrotoxicity	+	0.5180	51.80%
Acute Oral Toxicity (c)	I	0.4548	45.48%
Estrogen receptor binding	+	0.8031	80.31%
Androgen receptor binding	-	0.4919	49.19%
Thyroid receptor binding	+	0.6832	68.32%
Glucocorticoid receptor binding	+	0.8383	83.83%
Aromatase binding	+	0.7277	72.77%
PPAR gamma	-	0.6385	63.85%
Honey bee toxicity	-	0.8765	87.65%
Biodegradation	-	0.6250	62.50%
Crustacea aquatic toxicity	+	0.5400	54.00%
Fish aquatic toxicity	+	0.9954	99.54%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4040	P28482	MAP kinase ERK2	92.77%	83.82%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	91.74%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	90.02%	96.09%
CHEMBL253	P34972	Cannabinoid CB2 receptor	89.87%	97.25%
CHEMBL221	P23219	Cyclooxygenase-1	88.47%	90.17%
CHEMBL3137262	O60341	LSD1/CoREST complex	84.74%	97.09%
CHEMBL241	Q14432	Phosphodiesterase 3A	84.14%	92.94%
CHEMBL5608	Q16288	NT-3 growth factor receptor	83.83%	95.89%
CHEMBL1977	P11473	Vitamin D receptor	83.49%	99.43%
CHEMBL1994	P08235	Mineralocorticoid receptor	83.12%	100.00%
CHEMBL2581	P07339	Cathepsin D	81.04%	98.95%
CHEMBL1871	P10275	Androgen Receptor	80.59%	96.43%

Plants that contains it

• Pteris multifida
• Swietenia mahagoni

Cross-Links

• PubChem: 91668395
• NPASS: NPC312989