Andirobicin A glucoside

Details

• Internal ID: be16e751-986f-49a1-a1a5-a5dc8d5fa232
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroidal glycosides
• IUPAC Name: (8S,9R,13R,16R,17R)-17-[(E,2R)-2,3-dihydroxy-6-methoxy-6-methylhept-4-en-2-yl]-3,16-dihydroxy-4,9,13,14-tetramethyl-2-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-7,8,12,15,16,17-hexahydro-6H-cyclopenta[a]phenanthren-11-one
• SMILES (Canonical): CC1=C2CCC3C4(CC(C(C4(CC(=O)C3(C2=CC(=C1O)OC5C(C(C(C(O5)CO)O)O)O)C)C)C(C)(C(C=CC(C)(C)OC)O)O)O)C
• SMILES (Isomeric): CC1=C2CC[C@@H]3[C@](C2=CC(=C1O)O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O)(C(=O)C[C@]5(C3(C[C@H]([C@@H]5[C@](C)(C(/C=C/C(C)(C)OC)O)O)O)C)C)C
• InChI: InChI=1S/C36H54O12/c1-17-18-9-10-23-33(4)14-20(38)30(36(7,45)24(39)11-12-32(2,3)46-8)34(33,5)15-25(40)35(23,6)19(18)13-21(26(17)41)47-31-29(44)28(43)27(42)22(16-37)48-31/h11-13,20,22-24,27-31,37-39,41-45H,9-10,14-16H2,1-8H3/b12-11+/t20-,22-,23+,24?,27-,28+,29-,30+,31-,33?,34-,35+,36+/m1/s1
• InChI Key: FSGJPKCVUUKVDV-IRFBWZKWSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₃₆H₅₄O₁₂
• Molecular Weight: 678.80 g/mol
• Exact Mass: 678.36152715 g/mol
• Topological Polar Surface Area (TPSA): 207.00 Ų
• XlogP: 1.70
• Atomic LogP (AlogP): 1.16
• H-Bond Acceptor: 12
• H-Bond Donor: 8
• Rotatable Bonds: 8

Synonyms

• 151703-09-2
• (8S,9R,13R,16R,17R)-17-[(E,2R)-2,3-dihydroxy-6-methoxy-6-methylhept-4-en-2-yl]-3,16-dihydroxy-4,9,13,14-tetramethyl-2-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-7,8,12,15,16,17-hexahydro-6H-cyclopenta[a]phenanthren-11-one
• 19-nor-1,2,3,4,5,10-dehydro-25-methoxy-2-O-glucopyranosyl-3,16,20,22-tetrahydroxy-11-oxocucurbit-23-ene
• 19-Norcholesta-1,3,5(10),23-tetraen-11-one, 2-(beta-D-glucopyranosyloxy)-3,16,20,22-tetrahydroxy-25-methoxy-4,9,14-trimethyl-, (9beta,16alpha)-
• (8S,9R,13R,16R,17R)-17-((E,2R)-2,3-dihydroxy-6-methoxy-6-methylhept-4-en-2-yl)-3,16-dihydroxy-4,9,13,14-tetramethyl-2-((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl)oxy-7,8,12,15,16,17-hexahydro-6H-cyclopenta(a)phenanthren-11-one
• RefChem:112594
• 29-Nor-1,2,3,4,5,10-dehydro-25-methoxy-2-O-glucopyranosyl-3,16,20,22-tetrahydroxy-11-oxocucurbit-23-ene

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8994	89.94%
Caco-2	-	0.8479	84.79%
Blood Brain Barrier	-	0.6000	60.00%
Human oral bioavailability	-	0.7286	72.86%
Subcellular localzation	Mitochondria	0.7659	76.59%
OATP2B1 inhibitior	-	0.8621	86.21%
OATP1B1 inhibitior	+	0.8327	83.27%
OATP1B3 inhibitior	+	0.8604	86.04%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.7792	77.92%
BSEP inhibitior	+	0.8414	84.14%
P-glycoprotein inhibitior	+	0.7514	75.14%
P-glycoprotein substrate	+	0.5753	57.53%
CYP3A4 substrate	+	0.7218	72.18%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8563	85.63%
CYP3A4 inhibition	-	0.7099	70.99%
CYP2C9 inhibition	-	0.8049	80.49%
CYP2C19 inhibition	-	0.8195	81.95%
CYP2D6 inhibition	-	0.9162	91.62%
CYP1A2 inhibition	-	0.5293	52.93%
CYP2C8 inhibition	+	0.7047	70.47%
CYP inhibitory promiscuity	-	0.8982	89.82%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.7187	71.87%
Eye corrosion	-	0.9924	99.24%
Eye irritation	-	0.9124	91.24%
Skin irritation	-	0.7101	71.01%
Skin corrosion	-	0.9498	94.98%
Ames mutagenesis	-	0.6100	61.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6674	66.74%
Micronuclear	-	0.8500	85.00%
Hepatotoxicity	-	0.6098	60.98%
skin sensitisation	-	0.9046	90.46%
Respiratory toxicity	+	0.6667	66.67%
Reproductive toxicity	+	0.8889	88.89%
Mitochondrial toxicity	+	0.7125	71.25%
Nephrotoxicity	-	0.6476	64.76%
Acute Oral Toxicity (c)	I	0.3348	33.48%
Estrogen receptor binding	+	0.7576	75.76%
Androgen receptor binding	+	0.7353	73.53%
Thyroid receptor binding	+	0.5231	52.31%
Glucocorticoid receptor binding	+	0.8045	80.45%
Aromatase binding	+	0.7266	72.66%
PPAR gamma	+	0.7170	71.70%
Honey bee toxicity	-	0.6554	65.54%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.5400	54.00%
Fish aquatic toxicity	+	0.9768	97.68%

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	99.68%	91.11%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	99.38%	85.14%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	95.84%	94.45%
CHEMBL2581	P07339	Cathepsin D	95.82%	98.95%
CHEMBL220	P22303	Acetylcholinesterase	94.79%	94.45%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.85%	95.56%
CHEMBL241	Q14432	Phosphodiesterase 3A	93.67%	92.94%
CHEMBL1293249	Q13887	Kruppel-like factor 5	93.22%	86.33%
CHEMBL3137262	O60341	LSD1/CoREST complex	91.90%	97.09%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	91.60%	96.09%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	90.72%	96.21%
CHEMBL1806	P11388	DNA topoisomerase II alpha	90.64%	89.00%
CHEMBL253	P34972	Cannabinoid CB2 receptor	90.48%	97.25%
CHEMBL5608	Q16288	NT-3 growth factor receptor	89.87%	95.89%
CHEMBL1994	P08235	Mineralocorticoid receptor	89.78%	100.00%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	89.49%	95.89%
CHEMBL2069156	Q14145	Kelch-like ECH-associated protein 1	87.66%	82.38%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	87.52%	91.07%
CHEMBL4581	P52732	Kinesin-like protein 1	87.36%	93.18%
CHEMBL3060	Q9Y345	Glycine transporter 2	87.13%	99.17%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	85.07%	94.00%
CHEMBL5469	Q14289	Protein tyrosine kinase 2 beta	84.86%	91.03%
CHEMBL204	P00734	Thrombin	84.79%	96.01%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	83.33%	100.00%
CHEMBL4829	O00763	Acetyl-CoA carboxylase 2	81.69%	98.00%
CHEMBL3401	O75469	Pregnane X receptor	81.50%	94.73%
CHEMBL5255	O00206	Toll-like receptor 4	81.45%	92.50%

Plants that contains it

• Fevillea trilobata

Cross-Links

• PubChem: 6443696
• LOTUS: LTS0145940
• wikiData: Q105000627