19-O-(2-O-beta-D-Apiofuranosyl-beta-D-glucopyranosyl)-3,14-dideoxyandrograpolide

Details

• Internal ID: ca902c1f-b8f2-47e4-ad6a-72479bdcf7bd
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Diterpene glycosides
• IUPAC Name: 4-[2-[(1R,4aS,5R,8aS)-5-[[(2R,3R,4S,5S,6R)-3-[(2S,3R,4R)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]-5,8a-dimethyl-2-methylidene-3,4,4a,6,7,8-hexahydro-1H-naphthalen-1-yl]ethyl]-2H-furan-5-one
• SMILES (Canonical): CC1(CCCC2(C1CCC(=C)C2CCC3=CCOC3=O)C)COC4C(C(C(C(O4)CO)O)O)OC5C(C(CO5)(CO)O)O
• SMILES (Isomeric): C[C@]1(CCC[C@@]2([C@@H]1CCC(=C)[C@H]2CCC3=CCOC3=O)C)CO[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O[C@H]5[C@@H]([C@](CO5)(CO)O)O
• InChI: InChI=1S/C31H48O12/c1-17-5-8-21-29(2,10-4-11-30(21,3)19(17)7-6-18-9-12-39-26(18)37)15-40-27-24(23(35)22(34)20(13-32)42-27)43-28-25(36)31(38,14-33)16-41-28/h9,19-25,27-28,32-36,38H,1,4-8,10-16H2,2-3H3/t19-,20-,21-,22-,23+,24-,25+,27-,28+,29+,30+,31-/m1/s1
• InChI Key: OOQRHGBPHULERW-DPGDLXMDSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₃₁H₄₈O₁₂
• Molecular Weight: 612.70 g/mol
• Exact Mass: 612.31457696 g/mol
• Topological Polar Surface Area (TPSA): 185.00 Ų
• XlogP: 1.40
• Atomic LogP (AlogP): 0.31
• H-Bond Acceptor: 12
• H-Bond Donor: 6
• Rotatable Bonds: 10

Synonyms

• DTXSID801099907
• 19-O-(2-O-beta-D-Apiofuranosyl-beta-D-glucopyranosyl)-3,14-dideoxyandrograpolide
• 2(5H)-Furanone, 3-[2-[(1R,4aS,5R,8aS)-5-[[(2-O-D-apio-beta-D-furanosyl-beta-D-glucopyranosyl)oxy]methyl]decahydro-5,8a-dimethyl-2-methylene-1-naphthalenyl]ethyl]-
• 869384-83-8

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7469	74.69%
Caco-2	-	0.8551	85.51%
Blood Brain Barrier	-	0.6250	62.50%
Human oral bioavailability	-	0.7429	74.29%
Subcellular localzation	Mitochondria	0.7735	77.35%
OATP2B1 inhibitior	-	0.5806	58.06%
OATP1B1 inhibitior	+	0.8361	83.61%
OATP1B3 inhibitior	+	0.9273	92.73%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.7250	72.50%
BSEP inhibitior	+	0.6750	67.50%
P-glycoprotein inhibitior	+	0.6447	64.47%
P-glycoprotein substrate	+	0.5000	50.00%
CYP3A4 substrate	+	0.7268	72.68%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8896	88.96%
CYP3A4 inhibition	-	0.9013	90.13%
CYP2C9 inhibition	-	0.9158	91.58%
CYP2C19 inhibition	-	0.9084	90.84%
CYP2D6 inhibition	-	0.9256	92.56%
CYP1A2 inhibition	-	0.8918	89.18%
CYP2C8 inhibition	+	0.6646	66.46%
CYP inhibitory promiscuity	-	0.9396	93.96%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6268	62.68%
Eye corrosion	-	0.9902	99.02%
Eye irritation	-	0.9256	92.56%
Skin irritation	+	0.5000	50.00%
Skin corrosion	-	0.9394	93.94%
Ames mutagenesis	-	0.5900	59.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8484	84.84%
Micronuclear	-	0.9000	90.00%
Hepatotoxicity	-	0.6198	61.98%
skin sensitisation	-	0.9025	90.25%
Respiratory toxicity	+	0.6444	64.44%
Reproductive toxicity	+	0.8778	87.78%
Mitochondrial toxicity	+	0.5500	55.00%
Nephrotoxicity	-	0.6643	66.43%
Acute Oral Toxicity (c)	I	0.6455	64.55%
Estrogen receptor binding	+	0.7622	76.22%
Androgen receptor binding	+	0.7075	70.75%
Thyroid receptor binding	-	0.5589	55.89%
Glucocorticoid receptor binding	+	0.5656	56.56%
Aromatase binding	+	0.6981	69.81%
PPAR gamma	+	0.6564	65.64%
Honey bee toxicity	-	0.7057	70.57%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.6100	61.00%
Fish aquatic toxicity	+	0.9678	96.78%

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	99.22%	91.11%
CHEMBL226	P30542	Adenosine A1 receptor	98.20%	95.93%
CHEMBL2581	P07339	Cathepsin D	96.33%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	95.86%	95.56%
CHEMBL253	P34972	Cannabinoid CB2 receptor	95.76%	97.25%
CHEMBL3137262	O60341	LSD1/CoREST complex	93.84%	97.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	92.04%	94.45%
CHEMBL1293255	P15428	15-hydroxyprostaglandin dehydrogenase [NAD+]	91.86%	83.57%
CHEMBL1994	P08235	Mineralocorticoid receptor	89.49%	100.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.59%	86.33%
CHEMBL1806	P11388	DNA topoisomerase II alpha	87.94%	89.00%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	86.24%	86.92%
CHEMBL5608	Q16288	NT-3 growth factor receptor	86.05%	95.89%
CHEMBL5255	O00206	Toll-like receptor 4	85.84%	92.50%
CHEMBL1907605	P24864	Cyclin-dependent kinase 2/cyclin E1	83.90%	92.88%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	83.04%	94.00%
CHEMBL5028	O14672	ADAM10	82.53%	97.50%
CHEMBL218	P21554	Cannabinoid CB1 receptor	82.12%	96.61%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	82.10%	99.23%
CHEMBL3401	O75469	Pregnane X receptor	82.01%	94.73%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	81.07%	82.69%
CHEMBL4051	P13569	Cystic fibrosis transmembrane conductance regulator	80.72%	95.71%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	80.17%	91.24%
CHEMBL5203	P33316	dUTP pyrophosphatase	80.00%	99.18%

Plants that contains it

• Andrographis paniculata

Cross-Links

• PubChem: 44575258
• NPASS: NPC183587
• LOTUS: LTS0098327
• wikiData: Q105195550