Ophiopogonin A

Details

• Internal ID: ec93cdf8-56af-4fc4-9c73-981e4045108c
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroidal glycosides > Steroidal saponins
• IUPAC Name: [(2S,3R,4R,5S,6S)-2-[(2R,3R,4S,5R,6R)-4,5-dihydroxy-2-[(1S,2S,4S,5'R,6R,7S,8R,9S,12S,13R,14R,16R)-16-hydroxy-5',7,9,13-tetramethylspiro[5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icos-18-ene-6,2'-oxane]-14-yl]oxy-6-methyloxan-3-yl]oxy-3,5-dihydroxy-6-methyloxan-4-yl] acetate
• SMILES (Canonical): CC1CCC2(C(C3C(O2)CC4C3(CCC5C4CC=C6C5(C(CC(C6)O)OC7C(C(C(C(O7)C)O)O)OC8C(C(C(C(O8)C)O)OC(=O)C)O)C)C)C)OC1
• SMILES (Isomeric): C[C@@H]1CC[C@@]2([C@H]([C@H]3[C@@H](O2)C[C@@H]4[C@@]3(CC[C@H]5[C@H]4CC=C6[C@@]5([C@@H](C[C@@H](C6)O)O[C@H]7[C@@H]([C@H]([C@H]([C@H](O7)C)O)O)O[C@H]8[C@@H]([C@@H]([C@H]([C@@H](O8)C)O)OC(=O)C)O)C)C)C)OC1
• InChI: InChI=1S/C41H64O13/c1-18-10-13-41(48-17-18)19(2)30-28(54-41)16-27-25-9-8-23-14-24(43)15-29(40(23,7)26(25)11-12-39(27,30)6)52-38-36(33(46)31(44)20(3)50-38)53-37-34(47)35(51-22(5)42)32(45)21(4)49-37/h8,18-21,24-38,43-47H,9-17H2,1-7H3/t18-,19+,20-,21+,24-,25-,26+,27+,28+,29-,30+,31+,32+,33+,34-,35-,36-,37+,38+,39+,40+,41-/m1/s1
• InChI Key: KSIVGTKSVYIZEB-GDUJLLAZSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₄₁H₆₄O₁₃
• Molecular Weight: 764.90 g/mol
• Exact Mass: 764.43469209 g/mol
• Topological Polar Surface Area (TPSA): 183.00 Ų
• XlogP: 3.10
• Atomic LogP (AlogP): 2.96
• H-Bond Acceptor: 13
• H-Bond Donor: 5
• Rotatable Bonds: 5

Synonyms

• [(2S,3R,4R,5S,6S)-2-[(2R,3R,4S,5R,6R)-4,5-dihydroxy-2-[(1S,2S,4S,5'R,6R,7S,8R,9S,12S,13R,14R,16R)-16-hydroxy-5',7,9,13-tetramethylspiro[5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icos-18-ene-6,2'-oxane]-14-yl]oxy-6-methyloxan-3-yl]oxy-3,5-dihydroxy-6-methyloxan-4-yl] acetate
• ((2S,3R,4R,5S,6S)-2-((2R,3R,4S,5R,6R)-4,5-dihydroxy-2-((1S,2S,4S,5'R,6R,7S,8R,9S,12S,13R,14R,16R)-16-hydroxy-5',7,9,13-tetramethylspiro(5-oxapentacyclo(10.8.0.02,9.04,8.013,18)icos-18-ene-6,2'-oxane)-14-yl)oxy-6-methyloxan-3-yl)oxy-3,5-dihydroxy-6-methyloxan-4-yl) acetate
• RefChem:1093894
• 11054-24-3
• Lirioprolioside B
• Liriopeside B
• 182284-68-0
• orb1684356
• SCHEMBL29395895
• CHEBI:80882
• DTXSID10673002
• HY-N1960
• MFCD11111458
• AKOS016010663
• FS-9826
• CS-0018278
• C17041
• Q27151382
• (1beta,3beta,25R)-3-Hydroxyspirost-5-en-1-yl 2-O-(3-O-acetyl-6-deoxy-alpha-L-mannopyranosyl)-6-deoxy-beta-D-galactopyranoside

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9394	93.94%
Caco-2	-	0.8798	87.98%
Blood Brain Barrier	-	0.7000	70.00%
Human oral bioavailability	-	0.7286	72.86%
Subcellular localzation	Mitochondria	0.8031	80.31%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8720	87.20%
OATP1B3 inhibitior	+	0.9537	95.37%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.7250	72.50%
BSEP inhibitior	+	0.6493	64.93%
P-glycoprotein inhibitior	+	0.7383	73.83%
P-glycoprotein substrate	+	0.5851	58.51%
CYP3A4 substrate	+	0.7599	75.99%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8767	87.67%
CYP3A4 inhibition	-	0.8984	89.84%
CYP2C9 inhibition	-	0.9312	93.12%
CYP2C19 inhibition	-	0.9594	95.94%
CYP2D6 inhibition	-	0.9253	92.53%
CYP1A2 inhibition	-	0.8773	87.73%
CYP2C8 inhibition	+	0.7380	73.80%
CYP inhibitory promiscuity	-	0.9516	95.16%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.4749	47.49%
Eye corrosion	-	0.9895	98.95%
Eye irritation	-	0.9186	91.86%
Skin irritation	+	0.5663	56.63%
Skin corrosion	-	0.9326	93.26%
Ames mutagenesis	-	0.8000	80.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7395	73.95%
Micronuclear	-	0.8100	81.00%
Hepatotoxicity	-	0.6851	68.51%
skin sensitisation	-	0.8797	87.97%
Respiratory toxicity	+	0.7667	76.67%
Reproductive toxicity	+	0.9222	92.22%
Mitochondrial toxicity	+	0.6875	68.75%
Nephrotoxicity	-	0.6924	69.24%
Acute Oral Toxicity (c)	I	0.3923	39.23%
Estrogen receptor binding	+	0.7870	78.70%
Androgen receptor binding	+	0.7189	71.89%
Thyroid receptor binding	-	0.5828	58.28%
Glucocorticoid receptor binding	+	0.6676	66.76%
Aromatase binding	+	0.7152	71.52%
PPAR gamma	+	0.7273	72.73%
Honey bee toxicity	-	0.5550	55.50%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	+	0.5745	57.45%
Fish aquatic toxicity	+	0.9642	96.42%

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	98.80%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.73%	91.11%
CHEMBL1806	P11388	DNA topoisomerase II alpha	94.36%	89.00%
CHEMBL226	P30542	Adenosine A1 receptor	93.63%	95.93%
CHEMBL1994	P08235	Mineralocorticoid receptor	93.06%	100.00%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	92.44%	95.89%
CHEMBL1293249	Q13887	Kruppel-like factor 5	92.05%	86.33%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	91.05%	94.45%
CHEMBL5255	O00206	Toll-like receptor 4	90.53%	92.50%
CHEMBL3137262	O60341	LSD1/CoREST complex	90.17%	97.09%
CHEMBL3401	O75469	Pregnane X receptor	85.17%	94.73%
CHEMBL3922	P50579	Methionine aminopeptidase 2	85.01%	97.28%
CHEMBL2581	P07339	Cathepsin D	84.85%	98.95%
CHEMBL221	P23219	Cyclooxygenase-1	83.90%	90.17%
CHEMBL340	P08684	Cytochrome P450 3A4	83.61%	91.19%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	82.84%	95.56%
CHEMBL5028	O14672	ADAM10	82.56%	97.50%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	82.23%	94.00%
CHEMBL332	P03956	Matrix metalloproteinase-1	82.21%	94.50%
CHEMBL5608	Q16288	NT-3 growth factor receptor	81.53%	95.89%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	80.19%	92.62%
CHEMBL3359	P21462	Formyl peptide receptor 1	80.10%	93.56%

Plants that contains it

• Liriope muscari
• Ophiopogon japonicus

Cross-Links

• PubChem: 46173858
• NPASS: NPC229133