(1R,2S,3R,5R,6S,9R,10R,13R,15S)-6-[(E,4S,5S)-4,5-dihydroxy-6-methoxy-6-methylhept-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: 04222266-7d5c-4533-8562-58eea3edcc59
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Triterpenoids
• IUPAC Name: (1R,2S,3R,5R,6S,9R,10R,13R,15S)-6-[(E,4S,5S)-4,5-dihydroxy-6-methoxy-6-methylhept-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(C(C(C)(C)OC)O)O)C1CCC2(C1CC(C3C2(CCC4C35CCC(C4(C)C)(OC5)O)C)O)C
• SMILES (Isomeric): C/C(=C\[C@@H]([C@@H](C(C)(C)OC)O)O)/[C@H]1CC[C@@]2([C@@H]1C[C@H]([C@H]3[C@]2(CC[C@@H]4[C@]35CC[C@@](C4(C)C)(OC5)O)C)O)C
• InChI: InChI=1S/C31H52O6/c1-18(15-22(33)25(34)27(4,5)36-8)19-9-11-28(6)20(19)16-21(32)24-29(28,7)12-10-23-26(2,3)31(35)14-13-30(23,24)17-37-31/h15,19-25,32-35H,9-14,16-17H2,1-8H3/b18-15+/t19-,20-,21-,22+,23+,24+,25+,28-,29-,30-,31+/m1/s1
• InChI Key: ANFJBMXRWPPYJK-ZUKOLFMSSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₃₁H₅₂O₆
• Molecular Weight: 520.70 g/mol
• Exact Mass: 520.37638937 g/mol
• Topological Polar Surface Area (TPSA): 99.40 Ų
• XlogP: 4.60
• Atomic LogP (AlogP): 4.43
• H-Bond Acceptor: 6
• H-Bond Donor: 4
• Rotatable Bonds: 5

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9267	92.67%
Caco-2	-	0.6877	68.77%
Blood Brain Barrier	-	0.6250	62.50%
Human oral bioavailability	-	0.6857	68.57%
Subcellular localzation	Mitochondria	0.7707	77.07%
OATP2B1 inhibitior	-	0.5746	57.46%
OATP1B1 inhibitior	+	0.8500	85.00%
OATP1B3 inhibitior	+	0.9304	93.04%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.7542	75.42%
BSEP inhibitior	+	0.7670	76.70%
P-glycoprotein inhibitior	-	0.5000	50.00%
P-glycoprotein substrate	+	0.5409	54.09%
CYP3A4 substrate	+	0.7097	70.97%
CYP2C9 substrate	-	0.8090	80.90%
CYP2D6 substrate	-	0.8026	80.26%
CYP3A4 inhibition	-	0.8921	89.21%
CYP2C9 inhibition	-	0.7869	78.69%
CYP2C19 inhibition	-	0.8143	81.43%
CYP2D6 inhibition	-	0.9298	92.98%
CYP1A2 inhibition	-	0.6774	67.74%
CYP2C8 inhibition	+	0.6222	62.22%
CYP inhibitory promiscuity	-	0.9407	94.07%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.6470	64.70%
Eye corrosion	-	0.9908	99.08%
Eye irritation	-	0.9308	93.08%
Skin irritation	-	0.5837	58.37%
Skin corrosion	-	0.9453	94.53%
Ames mutagenesis	-	0.5700	57.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6477	64.77%
Micronuclear	-	0.8100	81.00%
Hepatotoxicity	-	0.6750	67.50%
skin sensitisation	-	0.8553	85.53%
Respiratory toxicity	+	0.6000	60.00%
Reproductive toxicity	+	0.8778	87.78%
Mitochondrial toxicity	+	0.6875	68.75%
Nephrotoxicity	+	0.5837	58.37%
Acute Oral Toxicity (c)	I	0.4513	45.13%
Estrogen receptor binding	+	0.7565	75.65%
Androgen receptor binding	+	0.7326	73.26%
Thyroid receptor binding	+	0.5576	55.76%
Glucocorticoid receptor binding	+	0.7174	71.74%
Aromatase binding	+	0.7112	71.12%
PPAR gamma	+	0.5909	59.09%
Honey bee toxicity	-	0.6069	60.69%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	-	0.6600	66.00%
Fish aquatic toxicity	+	0.9473	94.73%

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	99.39%	97.25%
CHEMBL1914	P06276	Butyrylcholinesterase	98.04%	95.00%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.11%	91.11%
CHEMBL3137262	O60341	LSD1/CoREST complex	95.62%	97.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	92.84%	94.45%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	92.67%	97.14%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	92.60%	96.09%
CHEMBL206	P03372	Estrogen receptor alpha	92.57%	97.64%
CHEMBL233	P35372	Mu opioid receptor	91.87%	97.93%
CHEMBL6136	O60341	Lysine-specific histone demethylase 1	90.51%	95.58%
CHEMBL5469	Q14289	Protein tyrosine kinase 2 beta	90.14%	91.03%
CHEMBL5608	Q16288	NT-3 growth factor receptor	89.96%	95.89%
CHEMBL4227	P25090	Lipoxin A4 receptor	89.86%	100.00%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	89.07%	85.14%
CHEMBL2581	P07339	Cathepsin D	88.38%	98.95%
CHEMBL1293316	Q9HBX9	Relaxin receptor 1	88.31%	82.50%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	87.75%	82.69%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	87.43%	100.00%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	87.16%	96.38%
CHEMBL1994	P08235	Mineralocorticoid receptor	87.10%	100.00%
CHEMBL4005	P42336	PI3-kinase p110-alpha subunit	86.87%	97.47%
CHEMBL259	P32245	Melanocortin receptor 4	86.08%	95.38%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	85.85%	91.07%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	85.62%	96.77%
CHEMBL3267	P48736	PI3-kinase p110-gamma subunit	85.55%	95.71%
CHEMBL2413	P32246	C-C chemokine receptor type 1	84.54%	89.50%
CHEMBL1902	P62942	FK506-binding protein 1A	83.88%	97.05%
CHEMBL340	P08684	Cytochrome P450 3A4	82.91%	91.19%
CHEMBL268	P43235	Cathepsin K	82.01%	96.85%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	80.85%	89.62%
CHEMBL1937	Q92769	Histone deacetylase 2	80.34%	94.75%
CHEMBL5888	Q99558	Mitogen-activated protein kinase kinase kinase 14	80.30%	100.00%

Plants that contains it

• Varronia multispicata

Cross-Links

• PubChem: 162964051
• LOTUS: LTS0122857
• wikiData: Q104915113