(1R,2R,5S,8S,9S,10R,11R,13R)-5-hydroxy-11-methyl-6-methylidene-16-oxo-13-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-15-oxapentacyclo[9.3.2.15,8.01,10.02,8]heptadecane-9-carboxylic acid

Details

• Internal ID: c4c29a6d-063f-41e8-acb9-b360aa29eedd
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Diterpene glycosides
• IUPAC Name: (1R,2R,5S,8S,9S,10R,11R,13R)-5-hydroxy-11-methyl-6-methylidene-16-oxo-13-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-15-oxapentacyclo[9.3.2.15,8.01,10.02,8]heptadecane-9-carboxylic acid
• SMILES (Canonical): CC12CC(CC3(C1C(C45C3CCC(C4)(C(=C)C5)O)C(=O)O)OC2=O)OC6C(C(C(C(O6)CO)O)O)O
• SMILES (Isomeric): C[C@@]12C[C@H](C[C@@]3([C@@H]1[C@@H]([C@]45[C@H]3CC[C@](C4)(C(=C)C5)O)C(=O)O)OC2=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O
• InChI: InChI=1S/C25H34O11/c1-10-5-23-9-24(10,33)4-3-13(23)25-7-11(34-20-17(29)16(28)15(27)12(8-26)35-20)6-22(2,21(32)36-25)18(25)14(23)19(30)31/h11-18,20,26-29,33H,1,3-9H2,2H3,(H,30,31)/t11-,12-,13-,14-,15-,16+,17-,18-,20-,22-,23+,24+,25-/m1/s1
• InChI Key: LCQKMIMLBQEMSB-VMWKOPFVSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₅H₃₄O₁₁
• Molecular Weight: 510.50 g/mol
• Exact Mass: 510.21011190 g/mol
• Topological Polar Surface Area (TPSA): 183.00 Ų
• XlogP: -1.40
• Atomic LogP (AlogP): -0.92
• H-Bond Acceptor: 10
• H-Bond Donor: 6
• Rotatable Bonds: 4

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7041	70.41%
Caco-2	-	0.8340	83.40%
Blood Brain Barrier	-	0.5750	57.50%
Human oral bioavailability	-	0.8143	81.43%
Subcellular localzation	Mitochondria	0.7865	78.65%
OATP2B1 inhibitior	-	0.7201	72.01%
OATP1B1 inhibitior	+	0.8851	88.51%
OATP1B3 inhibitior	+	0.9562	95.62%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.7303	73.03%
BSEP inhibitior	-	0.5805	58.05%
P-glycoprotein inhibitior	-	0.6219	62.19%
P-glycoprotein substrate	-	0.7388	73.88%
CYP3A4 substrate	+	0.6797	67.97%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8814	88.14%
CYP3A4 inhibition	-	0.8301	83.01%
CYP2C9 inhibition	-	0.8395	83.95%
CYP2C19 inhibition	-	0.8676	86.76%
CYP2D6 inhibition	-	0.9308	93.08%
CYP1A2 inhibition	-	0.8872	88.72%
CYP2C8 inhibition	+	0.4437	44.37%
CYP inhibitory promiscuity	-	0.9364	93.64%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.5808	58.08%
Eye corrosion	-	0.9881	98.81%
Eye irritation	-	0.9396	93.96%
Skin irritation	-	0.5652	56.52%
Skin corrosion	-	0.9339	93.39%
Ames mutagenesis	-	0.6854	68.54%
Human Ether-a-go-go-Related Gene inhibition	-	0.5000	50.00%
Micronuclear	-	0.8300	83.00%
Hepatotoxicity	-	0.7397	73.97%
skin sensitisation	-	0.8853	88.53%
Respiratory toxicity	+	0.6000	60.00%
Reproductive toxicity	+	0.8222	82.22%
Mitochondrial toxicity	+	0.7625	76.25%
Nephrotoxicity	+	0.6243	62.43%
Acute Oral Toxicity (c)	III	0.4617	46.17%
Estrogen receptor binding	+	0.7250	72.50%
Androgen receptor binding	+	0.6703	67.03%
Thyroid receptor binding	-	0.5230	52.30%
Glucocorticoid receptor binding	+	0.5714	57.14%
Aromatase binding	+	0.6818	68.18%
PPAR gamma	+	0.5561	55.61%
Honey bee toxicity	-	0.8632	86.32%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.6100	61.00%
Fish aquatic toxicity	+	0.9622	96.22%

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	97.95%	91.11%
CHEMBL2581	P07339	Cathepsin D	94.04%	98.95%
CHEMBL3137262	O60341	LSD1/CoREST complex	93.70%	97.09%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	92.58%	96.21%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	92.26%	94.45%
CHEMBL253	P34972	Cannabinoid CB2 receptor	92.14%	97.25%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	91.73%	96.09%
CHEMBL5255	O00206	Toll-like receptor 4	88.16%	92.50%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	86.89%	95.50%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.21%	95.56%
CHEMBL1806	P11388	DNA topoisomerase II alpha	85.95%	89.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	84.98%	95.89%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	84.85%	96.38%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	83.43%	93.04%
CHEMBL1994	P08235	Mineralocorticoid receptor	82.77%	100.00%
CHEMBL220	P22303	Acetylcholinesterase	81.67%	94.45%

Plants that contains it

• Phaseolus coccineus

Cross-Links

• PubChem: 101288419
• LOTUS: LTS0101774
• wikiData: Q105149946