3-[(2R,3R,4R,5R,6R)-5-hydroxy-3,4-bis[[(2S,3R,4R,5S,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy]-6-[[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxymethyl]oxan-2-yl]oxy-17-(2-hydroxy-6-methyl-4-oxohept-5-en-2-yl)-4,4,8,10,14-pentamethyl-1,2,3,5,6,7,9,11,13,15,16,17-dodecahydrocyclopenta[a]phenanthren-12-one

Details

• Internal ID: 407e8f1c-62a1-46d5-a129-f0a1ad3770af
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Triterpenoids
• IUPAC Name: 3-[(2R,3R,4R,5R,6R)-5-hydroxy-3,4-bis[[(2S,3R,4R,5S,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy]-6-[[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxymethyl]oxan-2-yl]oxy-17-(2-hydroxy-6-methyl-4-oxohept-5-en-2-yl)-4,4,8,10,14-pentamethyl-1,2,3,5,6,7,9,11,13,15,16,17-dodecahydrocyclopenta[a]phenanthren-12-one
• SMILES (Canonical): CC1C(C(C(C(O1)OCC2C(C(C(C(O2)OC3CCC4(C(C3(C)C)CCC5(C4CC(=O)C6C5(CCC6C(C)(CC(=O)C=C(C)C)O)C)C)C)OC7C(C(C(C(O7)C)O)O)O)OC8C(C(C(C(O8)C)O)O)O)O)O)O)O
• SMILES (Isomeric): C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)OC[C@@H]2[C@H]([C@H]([C@H]([C@@H](O2)OC3CCC4(C(C3(C)C)CCC5(C4CC(=O)C6C5(CCC6C(C)(CC(=O)C=C(C)C)O)C)C)C)O[C@H]7[C@@H]([C@@H]([C@@H]([C@@H](O7)C)O)O)O)O[C@H]8[C@@H]([C@@H]([C@@H]([C@@H](O8)C)O)O)O)O)O)O)O
• InChI: InChI=1S/C54H88O21/c1-22(2)18-26(55)20-54(11,67)27-12-16-53(10)33(27)28(56)19-31-51(8)15-14-32(50(6,7)30(51)13-17-52(31,53)9)73-49-45(75-48-43(66)40(63)36(59)25(5)71-48)44(74-47-42(65)39(62)35(58)24(4)70-47)37(60)29(72-49)21-68-46-41(64)38(61)34(57)23(3)69-46/h18,23-25,27,29-49,57-67H,12-17,19-21H2,1-11H3/t23-,24-,25-,27?,29+,30?,31?,32?,33?,34-,35+,36+,37+,38+,39+,40+,41+,42+,43+,44+,45+,46+,47-,48-,49-,51?,52?,53?,54?/m0/s1
• InChI Key: IJWRDCGWZHZENT-PXMMARCWSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₅₄H₈₈O₂₁
• Molecular Weight: 1073.30 g/mol
• Exact Mass: 1072.58180981 g/mol
• Topological Polar Surface Area (TPSA): 331.00 Ų
• XlogP: 0.30
• Atomic LogP (AlogP): 0.27
• H-Bond Acceptor: 21
• H-Bond Donor: 11
• Rotatable Bonds: 13

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8488	84.88%
Caco-2	-	0.8776	87.76%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	-	0.7000	70.00%
Subcellular localzation	Mitochondria	0.8499	84.99%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8320	83.20%
OATP1B3 inhibitior	+	0.8693	86.93%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.6558	65.58%
BSEP inhibitior	+	0.8885	88.85%
P-glycoprotein inhibitior	+	0.7541	75.41%
P-glycoprotein substrate	+	0.5000	50.00%
CYP3A4 substrate	+	0.7326	73.26%
CYP2C9 substrate	-	0.8024	80.24%
CYP2D6 substrate	-	0.8899	88.99%
CYP3A4 inhibition	-	0.8733	87.33%
CYP2C9 inhibition	-	0.8135	81.35%
CYP2C19 inhibition	-	0.9268	92.68%
CYP2D6 inhibition	-	0.9474	94.74%
CYP1A2 inhibition	-	0.9118	91.18%
CYP2C8 inhibition	+	0.6842	68.42%
CYP inhibitory promiscuity	-	0.9439	94.39%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6502	65.02%
Eye corrosion	-	0.9915	99.15%
Eye irritation	-	0.9015	90.15%
Skin irritation	+	0.5461	54.61%
Skin corrosion	-	0.9407	94.07%
Ames mutagenesis	-	0.6954	69.54%
Human Ether-a-go-go-Related Gene inhibition	+	0.7398	73.98%
Micronuclear	-	0.7800	78.00%
Hepatotoxicity	-	0.5764	57.64%
skin sensitisation	-	0.9007	90.07%
Respiratory toxicity	+	0.5444	54.44%
Reproductive toxicity	+	0.9111	91.11%
Mitochondrial toxicity	+	0.7125	71.25%
Nephrotoxicity	-	0.8005	80.05%
Acute Oral Toxicity (c)	I	0.4587	45.87%
Estrogen receptor binding	+	0.7882	78.82%
Androgen receptor binding	+	0.7511	75.11%
Thyroid receptor binding	-	0.4872	48.72%
Glucocorticoid receptor binding	+	0.7676	76.76%
Aromatase binding	+	0.6592	65.92%
PPAR gamma	+	0.7945	79.45%
Honey bee toxicity	-	0.6347	63.47%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	+	0.5600	56.00%
Fish aquatic toxicity	+	0.9817	98.17%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	99.29%	91.11%
CHEMBL1806	P11388	DNA topoisomerase II alpha	95.44%	89.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	94.42%	86.33%
CHEMBL2581	P07339	Cathepsin D	92.99%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	92.60%	96.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.34%	95.56%
CHEMBL5608	Q16288	NT-3 growth factor receptor	88.10%	95.89%
CHEMBL1994	P08235	Mineralocorticoid receptor	87.18%	100.00%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	86.57%	93.04%
CHEMBL253	P34972	Cannabinoid CB2 receptor	86.38%	97.25%
CHEMBL5255	O00206	Toll-like receptor 4	85.41%	92.50%
CHEMBL3137262	O60341	LSD1/CoREST complex	83.91%	97.09%
CHEMBL3401	O75469	Pregnane X receptor	82.75%	94.73%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	82.72%	94.00%
CHEMBL4051	P13569	Cystic fibrosis transmembrane conductance regulator	82.67%	95.71%
CHEMBL241	Q14432	Phosphodiesterase 3A	82.48%	92.94%
CHEMBL1902	P62942	FK506-binding protein 1A	81.99%	97.05%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	81.58%	94.45%
CHEMBL1951	P21397	Monoamine oxidase A	81.13%	91.49%
CHEMBL5028	O14672	ADAM10	80.28%	97.50%

Plants that contains it

• Gynostemma pentaphyllum

Cross-Links

• PubChem: 6325321
• NPASS: NPC230140