(1R,2S,3R,5R,6S,9R,10R,13R,15S)-6-[(E,4S)-4-[(2R)-3,3-dimethyloxiran-2-yl]-4-hydroxybut-2-en-2-yl]-9,10,14,14-tetramethyl-16-oxapentacyclo[13.2.2.01,13.02,10.05,9]nonadecane-3,15-diol

Details

• Internal ID: b0ae3710-e1f2-4de5-b2fd-f1f09035174c
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Triterpenoids
• IUPAC Name: (1R,2S,3R,5R,6S,9R,10R,13R,15S)-6-[(E,4S)-4-[(2R)-3,3-dimethyloxiran-2-yl]-4-hydroxybut-2-en-2-yl]-9,10,14,14-tetramethyl-16-oxapentacyclo[13.2.2.01,13.02,10.05,9]nonadecane-3,15-diol
• SMILES (Canonical): CC(=CC(C1C(O1)(C)C)O)C2CCC3(C2CC(C4C3(CCC5C46CCC(C5(C)C)(OC6)O)C)O)C
• SMILES (Isomeric): C/C(=C\[C@@H]([C@@H]1C(O1)(C)C)O)/[C@H]2CC[C@@]3([C@@H]2C[C@H]([C@H]4[C@]3(CC[C@@H]5[C@]46CC[C@@](C5(C)C)(OC6)O)C)O)C
• InChI: InChI=1S/C30H48O5/c1-17(14-21(32)24-26(4,5)35-24)18-8-10-27(6)19(18)15-20(31)23-28(27,7)11-9-22-25(2,3)30(33)13-12-29(22,23)16-34-30/h14,18-24,31-33H,8-13,15-16H2,1-7H3/b17-14+/t18-,19-,20-,21+,22+,23+,24-,27-,28-,29-,30+/m1/s1
• InChI Key: USYORMLHRJBQQS-OBMVDCASSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₀H₄₈O₅
• Molecular Weight: 488.70 g/mol
• Exact Mass: 488.35017463 g/mol
• Topological Polar Surface Area (TPSA): 82.40 Ų
• XlogP: 5.10
• Atomic LogP (AlogP): 4.83
• H-Bond Acceptor: 5
• H-Bond Donor: 3
• Rotatable Bonds: 3

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9590	95.90%
Caco-2	-	0.6479	64.79%
Blood Brain Barrier	-	0.5000	50.00%
Human oral bioavailability	-	0.6000	60.00%
Subcellular localzation	Mitochondria	0.7300	73.00%
OATP2B1 inhibitior	-	0.5754	57.54%
OATP1B1 inhibitior	+	0.8509	85.09%
OATP1B3 inhibitior	+	0.9248	92.48%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.6750	67.50%
BSEP inhibitior	+	0.7468	74.68%
P-glycoprotein inhibitior	-	0.5698	56.98%
P-glycoprotein substrate	+	0.5132	51.32%
CYP3A4 substrate	+	0.6832	68.32%
CYP2C9 substrate	-	0.8090	80.90%
CYP2D6 substrate	-	0.8005	80.05%
CYP3A4 inhibition	-	0.9041	90.41%
CYP2C9 inhibition	-	0.8216	82.16%
CYP2C19 inhibition	-	0.8854	88.54%
CYP2D6 inhibition	-	0.9343	93.43%
CYP1A2 inhibition	-	0.7949	79.49%
CYP2C8 inhibition	+	0.5909	59.09%
CYP inhibitory promiscuity	-	0.9411	94.11%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.5498	54.98%
Eye corrosion	-	0.9902	99.02%
Eye irritation	-	0.9403	94.03%
Skin irritation	-	0.5336	53.36%
Skin corrosion	-	0.9400	94.00%
Ames mutagenesis	-	0.6200	62.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6491	64.91%
Micronuclear	-	0.7200	72.00%
Hepatotoxicity	-	0.7000	70.00%
skin sensitisation	-	0.8165	81.65%
Respiratory toxicity	+	0.6333	63.33%
Reproductive toxicity	+	0.8889	88.89%
Mitochondrial toxicity	+	0.7125	71.25%
Nephrotoxicity	+	0.5963	59.63%
Acute Oral Toxicity (c)	I	0.4381	43.81%
Estrogen receptor binding	+	0.7609	76.09%
Androgen receptor binding	+	0.7459	74.59%
Thyroid receptor binding	+	0.5527	55.27%
Glucocorticoid receptor binding	+	0.7219	72.19%
Aromatase binding	+	0.7056	70.56%
PPAR gamma	+	0.5853	58.53%
Honey bee toxicity	-	0.6722	67.22%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	-	0.5900	59.00%
Fish aquatic toxicity	+	0.9593	95.93%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL253	P34972	Cannabinoid CB2 receptor	97.00%	97.25%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.76%	91.11%
CHEMBL6136	O60341	Lysine-specific histone demethylase 1	94.53%	95.58%
CHEMBL206	P03372	Estrogen receptor alpha	93.19%	97.64%
CHEMBL3137262	O60341	LSD1/CoREST complex	92.73%	97.09%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	92.56%	96.38%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	92.07%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	90.95%	94.45%
CHEMBL1994	P08235	Mineralocorticoid receptor	90.25%	100.00%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	89.89%	85.14%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	88.54%	97.14%
CHEMBL259	P32245	Melanocortin receptor 4	87.79%	95.38%
CHEMBL4681	P42330	Aldo-keto-reductase family 1 member C3	87.52%	89.05%
CHEMBL233	P35372	Mu opioid receptor	87.45%	97.93%
CHEMBL4227	P25090	Lipoxin A4 receptor	87.11%	100.00%
CHEMBL268	P43235	Cathepsin K	86.35%	96.85%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	86.33%	82.69%
CHEMBL4005	P42336	PI3-kinase p110-alpha subunit	84.91%	97.47%
CHEMBL1293316	Q9HBX9	Relaxin receptor 1	84.89%	82.50%
CHEMBL5469	Q14289	Protein tyrosine kinase 2 beta	84.38%	91.03%
CHEMBL1907601	P11802	Cyclin-dependent kinase 4/cyclin D1	84.34%	98.99%
CHEMBL5608	Q16288	NT-3 growth factor receptor	84.32%	95.89%
CHEMBL3837	P07711	Cathepsin L	84.17%	96.61%
CHEMBL1937	Q92769	Histone deacetylase 2	84.16%	94.75%
CHEMBL3922	P50579	Methionine aminopeptidase 2	83.55%	97.28%
CHEMBL2581	P07339	Cathepsin D	83.02%	98.95%
CHEMBL221	P23219	Cyclooxygenase-1	81.85%	90.17%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	81.79%	96.77%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	81.67%	95.89%
CHEMBL340	P08684	Cytochrome P450 3A4	81.48%	91.19%
CHEMBL2096618	P11274	Bcr/Abl fusion protein	81.44%	85.83%
CHEMBL5646	Q6L5J4	FML2_HUMAN	81.01%	100.00%
CHEMBL218	P21554	Cannabinoid CB1 receptor	80.92%	96.61%

Plants that contains it

• Varronia multispicata

Cross-Links

• PubChem: 163062917
• LOTUS: LTS0208724
• wikiData: Q105278606