Cryptogranodoside A

Details

• Internal ID: 07725899-60d9-4af4-b8ae-6ffc1560ec9f
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroid lactones > Cardenolides and derivatives > Cardenolide glycosides and derivatives
• IUPAC Name: [(3S,5R,8R,9S,10S,13R,14S,16S,17R)-14-hydroxy-3-[(2R,4S,5S,6R)-5-hydroxy-4-methoxy-6-methyloxan-2-yl]oxy-10,13-dimethyl-17-(5-oxo-2H-furan-3-yl)-1,2,3,4,5,6,7,8,9,11,12,15,16,17-tetradecahydrocyclopenta[a]phenanthren-16-yl] acetate
• SMILES (Canonical): CC1C(C(CC(O1)OC2CCC3(C(C2)CCC4C3CCC5(C4(CC(C5C6=CC(=O)OC6)OC(=O)C)O)C)C)OC)O
• SMILES (Isomeric): C[C@@H]1[C@@H]([C@H](C[C@@H](O1)O[C@H]2CC[C@]3([C@@H](C2)CC[C@@H]4[C@@H]3CC[C@]5([C@@]4(C[C@@H]([C@@H]5C6=CC(=O)OC6)OC(=O)C)O)C)C)OC)O
• InChI: InChI=1S/C32H48O9/c1-17-29(35)24(37-5)14-27(39-17)41-21-8-10-30(3)20(13-21)6-7-23-22(30)9-11-31(4)28(19-12-26(34)38-16-19)25(40-18(2)33)15-32(23,31)36/h12,17,20-25,27-29,35-36H,6-11,13-16H2,1-5H3/t17-,20-,21+,22+,23-,24+,25+,27+,28+,29+,30+,31-,32+/m1/s1
• InChI Key: JLPDBLFIVFSOCC-YANMAMTOSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₃₂H₄₈O₉
• Molecular Weight: 576.70 g/mol
• Exact Mass: 576.32983310 g/mol
• Topological Polar Surface Area (TPSA): 121.00 Ų
• XlogP: 2.40
• Atomic LogP (AlogP): 3.68
• H-Bond Acceptor: 9
• H-Bond Donor: 2
• Rotatable Bonds: 5

Synonyms

• CHEMBL413068
• 5-alpha-Card-20(22)-enolide, 3-beta-(2,6-dideoxy-3-O-methylxylohexopyranoxyl)oxy)-14,16-dihydroxy-, 16-acetate
• 16beta-Acetoxy-14-hydroxy-3beta-[(3-O-methyl-2,6-dideoxy-beta-D-xylo-hexopyranosyl)oxy]-5beta,14beta-carda-20(22)-enolide
• 465-17-8

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9759	97.59%
Caco-2	-	0.8135	81.35%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	+	0.7000	70.00%
Subcellular localzation	Mitochondria	0.8454	84.54%
OATP2B1 inhibitior	-	0.5765	57.65%
OATP1B1 inhibitior	+	0.9293	92.93%
OATP1B3 inhibitior	+	0.9726	97.26%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.8364	83.64%
BSEP inhibitior	+	0.7261	72.61%
P-glycoprotein inhibitior	+	0.6932	69.32%
P-glycoprotein substrate	+	0.8234	82.34%
CYP3A4 substrate	+	0.7305	73.05%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.9071	90.71%
CYP3A4 inhibition	-	0.8309	83.09%
CYP2C9 inhibition	-	0.9043	90.43%
CYP2C19 inhibition	-	0.9471	94.71%
CYP2D6 inhibition	-	0.9540	95.40%
CYP1A2 inhibition	-	0.9087	90.87%
CYP2C8 inhibition	-	0.6203	62.03%
CYP inhibitory promiscuity	-	0.9394	93.94%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.4628	46.28%
Eye corrosion	-	0.9904	99.04%
Eye irritation	-	0.9349	93.49%
Skin irritation	+	0.4943	49.43%
Skin corrosion	-	0.9372	93.72%
Ames mutagenesis	-	0.5593	55.93%
Human Ether-a-go-go-Related Gene inhibition	-	0.3887	38.87%
Micronuclear	-	0.7400	74.00%
Hepatotoxicity	-	0.7342	73.42%
skin sensitisation	-	0.9150	91.50%
Respiratory toxicity	+	0.8889	88.89%
Reproductive toxicity	+	0.9333	93.33%
Mitochondrial toxicity	+	0.8125	81.25%
Nephrotoxicity	-	0.7210	72.10%
Acute Oral Toxicity (c)	I	0.8422	84.22%
Estrogen receptor binding	+	0.7191	71.91%
Androgen receptor binding	+	0.8096	80.96%
Thyroid receptor binding	-	0.6394	63.94%
Glucocorticoid receptor binding	+	0.7300	73.00%
Aromatase binding	+	0.6765	67.65%
PPAR gamma	+	0.6159	61.59%
Honey bee toxicity	-	0.6083	60.83%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	+	0.5400	54.00%
Fish aquatic toxicity	+	0.9692	96.92%

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	98.18%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.35%	91.11%
CHEMBL1994	P08235	Mineralocorticoid receptor	96.02%	100.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	94.64%	94.45%
CHEMBL1293249	Q13887	Kruppel-like factor 5	93.44%	86.33%
CHEMBL5608	Q16288	NT-3 growth factor receptor	92.46%	95.89%
CHEMBL3137262	O60341	LSD1/CoREST complex	91.66%	97.09%
CHEMBL241	Q14432	Phosphodiesterase 3A	90.46%	92.94%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	90.38%	96.77%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	86.23%	85.14%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	85.95%	99.23%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	84.91%	91.07%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	84.88%	82.69%
CHEMBL1806	P11388	DNA topoisomerase II alpha	84.33%	89.00%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	84.15%	94.33%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	83.29%	94.00%
CHEMBL5255	O00206	Toll-like receptor 4	82.86%	92.50%
CHEMBL4208	P20618	Proteasome component C5	82.59%	90.00%
CHEMBL5028	O14672	ADAM10	81.72%	97.50%
CHEMBL340	P08684	Cytochrome P450 3A4	81.53%	91.19%
CHEMBL1871	P10275	Androgen Receptor	81.47%	96.43%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	81.33%	95.89%
CHEMBL3713062	P10646	Tissue factor pathway inhibitor	80.29%	97.33%

Plants that contains it

• Aconitum brevicalcaratum
• Ammodendron conollyi
• Cirsium dipsacolepis
• Cocculus diversifolius
• Crinum kirkii
• Cryptostegia grandiflora
• Cryptotaenia japonica
• Cytisus scoparius
• Heliomeris longifolia var. annua
• Hypericum triquetrifolium
• Isodon japonicus
• Knightia deplanchei
• Mallotus rhamnifolius
• Malva sylvestris
• Mesembryanthemum emarcidum
• Nerium oleander
• Plantago lanceolata
• Ptilidium ciliare
• Rhododendron farrerae
• Scutellaria seleriana
• Solanum pimpinellifolium
• Teucrium pestalozzae
• Toxicodendron succedaneum
• Trichotosia subsessilis
• Trifolium apertum
• Tripodanthus acutifolius
• Veronica pectinata

Cross-Links

• PubChem: 44425149
• NPASS: NPC44899
• ChEMBL: CHEMBL413068
• LOTUS: LTS0008604
• wikiData: Q105130971