(4S)-4-[(3S,5R,8R,9R,10R,12R,13R,14R,17S)-3-[(2R,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-12-hydroxy-4,4,8,10,14-pentamethyl-2,3,5,6,7,9,11,12,13,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxypentanal

Details

• Internal ID: 9bf78cd7-368d-4c4a-9860-83ef71b3d588
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Triterpenoids
• IUPAC Name: (4S)-4-[(3S,5R,8R,9R,10R,12R,13R,14R,17S)-3-[(2R,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-12-hydroxy-4,4,8,10,14-pentamethyl-2,3,5,6,7,9,11,12,13,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxypentanal
• SMILES (Canonical): CC1(C2CCC3(C(C2(CCC1OC4C(C(C(C(O4)CO)O)O)OC5C(C(C(C(O5)CO)O)O)O)C)CC(C6C3(CCC6C(C)(CCC=O)OC7C(C(C(C(O7)CO)O)O)O)C)O)C)C
• SMILES (Isomeric): C[C@]12CC[C@@H](C([C@@H]1CC[C@@]3([C@@H]2C[C@H]([C@H]4[C@]3(CC[C@@H]4[C@](C)(CCC=O)O[C@H]5[C@@H]([C@H]([C@@H]([C@H](O5)CO)O)O)O)C)O)C)(C)C)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O[C@H]7[C@@H]([C@H]([C@@H]([C@H](O7)CO)O)O)O
• InChI: InChI=1S/C45H76O19/c1-41(2)25-9-14-43(4)26(16-21(50)28-20(8-13-44(28,43)5)45(6,11-7-15-46)64-39-36(58)33(55)30(52)23(18-48)60-39)42(25,3)12-10-27(41)62-40-37(34(56)31(53)24(19-49)61-40)63-38-35(57)32(54)29(51)22(17-47)59-38/h15,20-40,47-58H,7-14,16-19H2,1-6H3/t20-,21+,22+,23+,24+,25-,26+,27-,28-,29+,30+,31+,32-,33-,34-,35+,36+,37+,38-,39-,40-,42-,43+,44+,45-/m0/s1
• InChI Key: IGLJYCHASIODBT-VODKKTFRSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₄₅H₇₆O₁₉
• Molecular Weight: 921.10 g/mol
• Exact Mass: 920.49808019 g/mol
• Topological Polar Surface Area (TPSA): 315.00 Ų
• XlogP: -0.10
• Atomic LogP (AlogP): -1.79
• H-Bond Acceptor: 19
• H-Bond Donor: 12
• Rotatable Bonds: 13

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.5878	58.78%
Caco-2	-	0.8887	88.87%
Blood Brain Barrier	-	0.6250	62.50%
Human oral bioavailability	-	0.8143	81.43%
Subcellular localzation	Mitochondria	0.7552	75.52%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.7923	79.23%
OATP1B3 inhibitior	+	0.8702	87.02%
MATE1 inhibitior	-	0.9812	98.12%
OCT2 inhibitior	-	0.6500	65.00%
BSEP inhibitior	+	0.7427	74.27%
P-glycoprotein inhibitior	+	0.7495	74.95%
P-glycoprotein substrate	-	0.7686	76.86%
CYP3A4 substrate	+	0.7259	72.59%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8508	85.08%
CYP3A4 inhibition	-	0.9394	93.94%
CYP2C9 inhibition	-	0.8941	89.41%
CYP2C19 inhibition	-	0.9060	90.60%
CYP2D6 inhibition	-	0.9604	96.04%
CYP1A2 inhibition	-	0.9213	92.13%
CYP2C8 inhibition	+	0.5851	58.51%
CYP inhibitory promiscuity	-	0.9775	97.75%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6894	68.94%
Eye corrosion	-	0.9919	99.19%
Eye irritation	-	0.9050	90.50%
Skin irritation	-	0.6714	67.14%
Skin corrosion	-	0.9539	95.39%
Ames mutagenesis	-	0.7800	78.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8139	81.39%
Micronuclear	-	0.9000	90.00%
Hepatotoxicity	+	0.5741	57.41%
skin sensitisation	-	0.9351	93.51%
Respiratory toxicity	+	0.5556	55.56%
Reproductive toxicity	+	0.7667	76.67%
Mitochondrial toxicity	-	0.5750	57.50%
Nephrotoxicity	-	0.7451	74.51%
Acute Oral Toxicity (c)	I	0.5589	55.89%
Estrogen receptor binding	+	0.7550	75.50%
Androgen receptor binding	+	0.7492	74.92%
Thyroid receptor binding	-	0.5689	56.89%
Glucocorticoid receptor binding	+	0.7151	71.51%
Aromatase binding	+	0.6622	66.22%
PPAR gamma	+	0.7628	76.28%
Honey bee toxicity	-	0.5600	56.00%
Biodegradation	-	0.6000	60.00%
Crustacea aquatic toxicity	-	0.5000	50.00%
Fish aquatic toxicity	+	0.8367	83.67%

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	97.15%	97.25%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.35%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.15%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	93.01%	97.09%
CHEMBL3714130	P46095	G-protein coupled receptor 6	90.76%	97.36%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.63%	86.33%
CHEMBL1994	P08235	Mineralocorticoid receptor	88.78%	100.00%
CHEMBL218	P21554	Cannabinoid CB1 receptor	88.43%	96.61%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.40%	95.56%
CHEMBL5608	Q16288	NT-3 growth factor receptor	88.18%	95.89%
CHEMBL2581	P07339	Cathepsin D	88.04%	98.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	87.72%	89.00%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	86.16%	97.14%
CHEMBL4227	P25090	Lipoxin A4 receptor	84.27%	100.00%
CHEMBL241	Q14432	Phosphodiesterase 3A	83.34%	92.94%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	83.22%	95.50%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	83.01%	96.21%
CHEMBL6136	O60341	Lysine-specific histone demethylase 1	81.80%	95.58%
CHEMBL5028	O14672	ADAM10	81.57%	97.50%
CHEMBL5255	O00206	Toll-like receptor 4	81.45%	92.50%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	80.83%	100.00%

Plants that contains it

• Panax ginseng

Cross-Links

• PubChem: 44627819
• LOTUS: LTS0011640
• wikiData: Q105112712