(3S,8S,9R,10R,13R,14S,16S,17R)-3-[(2R,3R,4R,5S,6R)-5-[(2S,3R,4R)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy-3,4-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-16-hydroxy-17-[(2S,5S)-5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-4,4,9,13,14-pentamethyl-1,2,3,7,8,10,12,15,16,17-decahydrocyclopenta[a]phenanthren-11-one

Details

• Internal ID: fee28ea0-499c-49ca-bca8-90ebf8580d2c
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroidal glycosides > Steroidal saponins > Cucurbitacin glycosides
• IUPAC Name: (3S,8S,9R,10R,13R,14S,16S,17R)-3-[(2R,3R,4R,5S,6R)-5-[(2S,3R,4R)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy-3,4-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-16-hydroxy-17-[(2S,5S)-5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-4,4,9,13,14-pentamethyl-1,2,3,7,8,10,12,15,16,17-decahydrocyclopenta[a]phenanthren-11-one
• SMILES (Canonical): CC1(C(CCC2C1=CCC3C2(C(=O)CC4(C3(CC(C4C5(CCC(O5)C(C)(C)O)C)O)C)C)C)OC6C(C(C(C(O6)CO)OC7C(C(CO7)(CO)O)O)O)O)C
• SMILES (Isomeric): C[C@]1(CC[C@H](O1)C(C)(C)O)[C@H]2[C@H](C[C@@]3([C@@]2(CC(=O)[C@@]4([C@H]3CC=C5[C@H]4CC[C@@H](C5(C)C)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O[C@H]7[C@@H]([C@](CO7)(CO)O)O)O)O)C)C)C)O
• InChI: InChI=1S/C41H66O14/c1-35(2)20-9-11-24-37(5)15-22(44)31(39(7)14-13-27(55-39)36(3,4)49)38(37,6)16-25(45)40(24,8)21(20)10-12-26(35)53-33-29(47)28(46)30(23(17-42)52-33)54-34-32(48)41(50,18-43)19-51-34/h9,21-24,26-34,42-44,46-50H,10-19H2,1-8H3/t21-,22+,23-,24+,26+,27+,28-,29-,30-,31+,32+,33+,34+,37+,38-,39+,40+,41-/m1/s1
• InChI Key: IOTJQIMOVXPYNO-RCSZUNTISA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₄₁H₆₆O₁₄
• Molecular Weight: 783.00 g/mol
• Exact Mass: 782.44525677 g/mol
• Topological Polar Surface Area (TPSA): 225.00 Ų
• XlogP: 0.10
• Atomic LogP (AlogP): 1.10
• H-Bond Acceptor: 14
• H-Bond Donor: 8
• Rotatable Bonds: 8

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8931	89.31%
Caco-2	-	0.8783	87.83%
Blood Brain Barrier	-	0.7000	70.00%
Human oral bioavailability	-	0.7714	77.14%
Subcellular localzation	Mitochondria	0.8712	87.12%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8566	85.66%
OATP1B3 inhibitior	+	0.8426	84.26%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	+	0.6338	63.38%
P-glycoprotein inhibitior	+	0.7511	75.11%
P-glycoprotein substrate	+	0.5622	56.22%
CYP3A4 substrate	+	0.7430	74.30%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8733	87.33%
CYP3A4 inhibition	-	0.8847	88.47%
CYP2C9 inhibition	-	0.8631	86.31%
CYP2C19 inhibition	-	0.9157	91.57%
CYP2D6 inhibition	-	0.9300	93.00%
CYP1A2 inhibition	-	0.9156	91.56%
CYP2C8 inhibition	+	0.6881	68.81%
CYP inhibitory promiscuity	-	0.9151	91.51%
UGT catelyzed	-	0.8000	80.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.5218	52.18%
Eye corrosion	-	0.9888	98.88%
Eye irritation	-	0.9126	91.26%
Skin irritation	-	0.5588	55.88%
Skin corrosion	-	0.9383	93.83%
Ames mutagenesis	-	0.7800	78.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7524	75.24%
Micronuclear	-	0.8500	85.00%
Hepatotoxicity	-	0.5278	52.78%
skin sensitisation	-	0.9052	90.52%
Respiratory toxicity	+	0.6111	61.11%
Reproductive toxicity	+	0.9333	93.33%
Mitochondrial toxicity	-	0.5875	58.75%
Nephrotoxicity	-	0.7060	70.60%
Acute Oral Toxicity (c)	I	0.5999	59.99%
Estrogen receptor binding	+	0.7507	75.07%
Androgen receptor binding	+	0.7516	75.16%
Thyroid receptor binding	-	0.5478	54.78%
Glucocorticoid receptor binding	+	0.7153	71.53%
Aromatase binding	+	0.6768	67.68%
PPAR gamma	+	0.7383	73.83%
Honey bee toxicity	-	0.6866	68.66%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.5500	55.00%
Fish aquatic toxicity	+	0.9652	96.52%

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	98.29%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	95.01%	95.56%
CHEMBL218	P21554	Cannabinoid CB1 receptor	94.52%	96.61%
CHEMBL226	P30542	Adenosine A1 receptor	93.79%	95.93%
CHEMBL3137262	O60341	LSD1/CoREST complex	93.77%	97.09%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	93.10%	94.00%
CHEMBL2581	P07339	Cathepsin D	92.93%	98.95%
CHEMBL1293249	Q13887	Kruppel-like factor 5	92.19%	86.33%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	91.30%	94.45%
CHEMBL5888	Q99558	Mitogen-activated protein kinase kinase kinase 14	89.36%	100.00%
CHEMBL1994	P08235	Mineralocorticoid receptor	89.26%	100.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	88.63%	89.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	88.57%	99.23%
CHEMBL253	P34972	Cannabinoid CB2 receptor	88.29%	97.25%
CHEMBL1937	Q92769	Histone deacetylase 2	88.13%	94.75%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	86.31%	96.77%
CHEMBL5608	Q16288	NT-3 growth factor receptor	85.17%	95.89%
CHEMBL241	Q14432	Phosphodiesterase 3A	85.12%	92.94%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	84.31%	92.62%
CHEMBL4581	P52732	Kinesin-like protein 1	83.83%	93.18%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	83.68%	96.09%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	83.52%	93.04%
CHEMBL3401	O75469	Pregnane X receptor	83.28%	94.73%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	82.55%	86.92%
CHEMBL3713062	P10646	Tissue factor pathway inhibitor	82.45%	97.33%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	82.31%	91.07%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	82.30%	97.14%
CHEMBL4051	P13569	Cystic fibrosis transmembrane conductance regulator	82.23%	95.71%
CHEMBL1871	P10275	Androgen Receptor	81.79%	96.43%
CHEMBL2959	Q08881	Tyrosine-protein kinase ITK/TSK	80.80%	95.00%
CHEMBL1293255	P15428	15-hydroxyprostaglandin dehydrogenase [NAD+]	80.75%	83.57%

Plants that contains it

• Gratiola officinalis

Cross-Links

• PubChem: 21575888
• LOTUS: LTS0009835
• wikiData: Q105116875