(3R,4S,5S,6R)-2-[2-[(1R,3aS,4S,5Z,9R,12aS)-4,9-dihydroxy-6-(hydroxymethyl)-3a,12a-dimethyl-10-methylidene-2,3,4,7,8,9,11,12-octahydro-1H-cyclopenta[11]annulen-1-yl]-2-methylpropoxy]-6-(hydroxymethyl)oxane-3,4,5-triol

Details

• Internal ID: 35969f7c-2483-4c97-b553-bfb023401f9d
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Diterpene glycosides
• IUPAC Name: (3R,4S,5S,6R)-2-[2-[(1R,3aS,4S,5Z,9R,12aS)-4,9-dihydroxy-6-(hydroxymethyl)-3a,12a-dimethyl-10-methylidene-2,3,4,7,8,9,11,12-octahydro-1H-cyclopenta[11]annulen-1-yl]-2-methylpropoxy]-6-(hydroxymethyl)oxane-3,4,5-triol
• SMILES (Canonical): CC12CCC(=C)C(CCC(=CC(C1(CCC2C(C)(C)COC3C(C(C(C(O3)CO)O)O)O)C)O)CO)O
• SMILES (Isomeric): C[C@@]12CCC(=C)[C@@H](CC/C(=C/[C@@H]([C@]1(CC[C@H]2C(C)(C)COC3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O)C)O)/CO)O
• InChI: InChI=1S/C28H48O9/c1-16-8-10-27(4)20(9-11-28(27,5)21(32)12-17(13-29)6-7-18(16)31)26(2,3)15-36-25-24(35)23(34)22(33)19(14-30)37-25/h12,18-25,29-35H,1,6-11,13-15H2,2-5H3/b17-12-/t18-,19-,20+,21+,22-,23+,24-,25?,27+,28-/m1/s1
• InChI Key: WPCOUSAJELDJIP-UJWPTSQRSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₈H₄₈O₉
• Molecular Weight: 528.70 g/mol
• Exact Mass: 528.32983310 g/mol
• Topological Polar Surface Area (TPSA): 160.00 Ų
• XlogP: 0.90
• Atomic LogP (AlogP): 1.02
• H-Bond Acceptor: 9
• H-Bond Donor: 7
• Rotatable Bonds: 6

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7047	70.47%
Caco-2	-	0.7873	78.73%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	-	0.7571	75.71%
Subcellular localzation	Mitochondria	0.6850	68.50%
OATP2B1 inhibitior	-	0.5779	57.79%
OATP1B1 inhibitior	+	0.8535	85.35%
OATP1B3 inhibitior	+	0.8762	87.62%
MATE1 inhibitior	-	0.9612	96.12%
OCT2 inhibitior	-	0.6500	65.00%
BSEP inhibitior	-	0.5681	56.81%
P-glycoprotein inhibitior	-	0.5473	54.73%
P-glycoprotein substrate	-	0.6995	69.95%
CYP3A4 substrate	+	0.6735	67.35%
CYP2C9 substrate	-	0.8025	80.25%
CYP2D6 substrate	-	0.8264	82.64%
CYP3A4 inhibition	-	0.9099	90.99%
CYP2C9 inhibition	-	0.7695	76.95%
CYP2C19 inhibition	-	0.8257	82.57%
CYP2D6 inhibition	-	0.9357	93.57%
CYP1A2 inhibition	-	0.8163	81.63%
CYP2C8 inhibition	+	0.5950	59.50%
CYP inhibitory promiscuity	-	0.9404	94.04%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9400	94.00%
Carcinogenicity (trinary)	Non-required	0.7059	70.59%
Eye corrosion	-	0.9883	98.83%
Eye irritation	-	0.9381	93.81%
Skin irritation	-	0.6124	61.24%
Skin corrosion	-	0.9440	94.40%
Ames mutagenesis	-	0.6100	61.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8192	81.92%
Micronuclear	-	0.9000	90.00%
Hepatotoxicity	-	0.7539	75.39%
skin sensitisation	-	0.8690	86.90%
Respiratory toxicity	-	0.5222	52.22%
Reproductive toxicity	+	0.7333	73.33%
Mitochondrial toxicity	+	0.5250	52.50%
Nephrotoxicity	-	0.5945	59.45%
Acute Oral Toxicity (c)	III	0.4599	45.99%
Estrogen receptor binding	+	0.6587	65.87%
Androgen receptor binding	+	0.6831	68.31%
Thyroid receptor binding	+	0.5865	58.65%
Glucocorticoid receptor binding	+	0.5870	58.70%
Aromatase binding	+	0.6879	68.79%
PPAR gamma	+	0.5981	59.81%
Honey bee toxicity	-	0.7668	76.68%
Biodegradation	-	0.6500	65.00%
Crustacea aquatic toxicity	-	0.6000	60.00%
Fish aquatic toxicity	+	0.9335	93.35%

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	98.02%	91.11%
CHEMBL253	P34972	Cannabinoid CB2 receptor	95.36%	97.25%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.92%	96.09%
CHEMBL2581	P07339	Cathepsin D	92.53%	98.95%
CHEMBL3137262	O60341	LSD1/CoREST complex	91.65%	97.09%
CHEMBL226	P30542	Adenosine A1 receptor	91.42%	95.93%
CHEMBL218	P21554	Cannabinoid CB1 receptor	90.62%	96.61%
CHEMBL5608	Q16288	NT-3 growth factor receptor	87.30%	95.89%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	86.85%	97.14%
CHEMBL1994	P08235	Mineralocorticoid receptor	85.99%	100.00%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	85.33%	95.89%
CHEMBL1977	P11473	Vitamin D receptor	85.27%	99.43%
CHEMBL4681	P42330	Aldo-keto-reductase family 1 member C3	85.10%	89.05%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	84.89%	91.71%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	82.61%	92.62%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	82.50%	94.00%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	81.77%	95.50%
CHEMBL233	P35372	Mu opioid receptor	80.93%	97.93%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	80.47%	95.56%
CHEMBL241	Q14432	Phosphodiesterase 3A	80.28%	92.94%

Plants that contains it

• Chrozophora plicata

Cross-Links

• PubChem: 162817256
• LOTUS: LTS0066097
• wikiData: Q105309792