Atropuroside D

Details

• Internal ID: 7935a284-44f6-4b66-8e01-1522a628edce
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroidal glycosides > Steroidal saponins
• IUPAC Name: (2R,3R,4S,5R,6R)-2-[(1S,2S,4S,6R,7S,8R,9S,12S,13R,14S,15S,16R)-15,16-dihydroxy-7,9,13-trimethyl-5'-methylidenespiro[5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icos-18-ene-6,2'-oxane]-14-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol
• SMILES (Canonical): CC1C2C(CC3C2(CCC4C3CC=C5C4(C(C(C(C5)O)O)OC6C(C(C(C(O6)CO)O)O)O)C)C)OC17CCC(=C)CO7
• SMILES (Isomeric): C[C@H]1[C@H]2[C@H](C[C@@H]3[C@@]2(CC[C@H]4[C@H]3CC=C5[C@@]4([C@@H]([C@H]([C@@H](C5)O)O)O[C@H]6[C@@H]([C@H]([C@H]([C@H](O6)CO)O)O)O)C)C)O[C@]17CCC(=C)CO7
• InChI: InChI=1S/C33H50O10/c1-15-7-10-33(40-14-15)16(2)24-22(43-33)12-20-18-6-5-17-11-21(35)25(36)29(32(17,4)19(18)8-9-31(20,24)3)42-30-28(39)27(38)26(37)23(13-34)41-30/h5,16,18-30,34-39H,1,6-14H2,2-4H3/t16-,18+,19-,20-,21+,22-,23+,24-,25-,26-,27-,28+,29+,30-,31-,32-,33+/m0/s1
• InChI Key: UGYIVDNSTBVZFU-ZXVGMJOFSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₃₃H₅₀O₁₀
• Molecular Weight: 606.70 g/mol
• Exact Mass: 606.34039779 g/mol
• Topological Polar Surface Area (TPSA): 158.00 Ų
• XlogP: 1.50
• Atomic LogP (AlogP): 1.40
• H-Bond Acceptor: 10
• H-Bond Donor: 6
• Rotatable Bonds: 3

Synonyms

• 2alpha,3beta-Dihydroxy-spirost-5,25(27)-dien-1beta-yl O-.beta.-D-galactopyranoside
• (2R,3R,4S,5R,6R)-2-[(2R)-dihydroxy-trimethyl-5'-methylene-spiro[[?]-2,2'-tetrahydropyran]yl]oxy-6-(hydroxymethyl)tetrahydropyran-3,4,5-triol

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7345	73.45%
Caco-2	-	0.8664	86.64%
Blood Brain Barrier	-	0.6750	67.50%
Human oral bioavailability	-	0.7000	70.00%
Subcellular localzation	Mitochondria	0.6911	69.11%
OATP2B1 inhibitior	-	0.7268	72.68%
OATP1B1 inhibitior	+	0.8692	86.92%
OATP1B3 inhibitior	+	0.8909	89.09%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.6000	60.00%
BSEP inhibitior	-	0.6715	67.15%
P-glycoprotein inhibitior	+	0.5919	59.19%
P-glycoprotein substrate	+	0.5304	53.04%
CYP3A4 substrate	+	0.7393	73.93%
CYP2C9 substrate	-	0.8054	80.54%
CYP2D6 substrate	-	0.8216	82.16%
CYP3A4 inhibition	-	0.9006	90.06%
CYP2C9 inhibition	-	0.9010	90.10%
CYP2C19 inhibition	-	0.9027	90.27%
CYP2D6 inhibition	-	0.9335	93.35%
CYP1A2 inhibition	-	0.8983	89.83%
CYP2C8 inhibition	+	0.7159	71.59%
CYP inhibitory promiscuity	-	0.9325	93.25%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.5433	54.33%
Eye corrosion	-	0.9884	98.84%
Eye irritation	-	0.9358	93.58%
Skin irritation	+	0.5100	51.00%
Skin corrosion	-	0.9400	94.00%
Ames mutagenesis	-	0.7470	74.70%
Human Ether-a-go-go-Related Gene inhibition	+	0.8183	81.83%
Micronuclear	-	0.8800	88.00%
Hepatotoxicity	-	0.7375	73.75%
skin sensitisation	-	0.9094	90.94%
Respiratory toxicity	+	0.7556	75.56%
Reproductive toxicity	+	0.9111	91.11%
Mitochondrial toxicity	+	0.5625	56.25%
Nephrotoxicity	-	0.7975	79.75%
Acute Oral Toxicity (c)	I	0.5214	52.14%
Estrogen receptor binding	+	0.7096	70.96%
Androgen receptor binding	+	0.7240	72.40%
Thyroid receptor binding	-	0.6193	61.93%
Glucocorticoid receptor binding	-	0.4658	46.58%
Aromatase binding	+	0.6894	68.94%
PPAR gamma	+	0.5998	59.98%
Honey bee toxicity	-	0.6282	62.82%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.5800	58.00%
Fish aquatic toxicity	+	0.9570	95.70%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.65%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.01%	91.11%
CHEMBL1994	P08235	Mineralocorticoid receptor	95.13%	100.00%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	93.95%	85.14%
CHEMBL226	P30542	Adenosine A1 receptor	93.37%	95.93%
CHEMBL3137262	O60341	LSD1/CoREST complex	92.34%	97.09%
CHEMBL4681	P42330	Aldo-keto-reductase family 1 member C3	88.45%	89.05%
CHEMBL237	P41145	Kappa opioid receptor	88.16%	98.10%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	88.12%	94.45%
CHEMBL2996	Q05655	Protein kinase C delta	88.09%	97.79%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.33%	86.33%
CHEMBL253	P34972	Cannabinoid CB2 receptor	86.82%	97.25%
CHEMBL5608	Q16288	NT-3 growth factor receptor	85.71%	95.89%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	85.44%	95.89%
CHEMBL2581	P07339	Cathepsin D	84.81%	98.95%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	83.74%	95.50%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	83.25%	91.24%
CHEMBL1977	P11473	Vitamin D receptor	82.97%	99.43%
CHEMBL3392948	Q9NP59	Solute carrier family 40 member 1	81.45%	95.00%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	81.22%	96.21%
CHEMBL1806	P11388	DNA topoisomerase II alpha	81.13%	89.00%
CHEMBL5028	O14672	ADAM10	80.81%	97.50%
CHEMBL5255	O00206	Toll-like receptor 4	80.32%	92.50%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	80.28%	94.00%
CHEMBL1937	Q92769	Histone deacetylase 2	80.22%	94.75%

Plants that contains it

• Maianthemum atropurpureum

Cross-Links

• PubChem: 11844172
• LOTUS: LTS0041881
• wikiData: Q105272649