Bacobitacin D

Details

• Internal ID: c179b41f-58ff-43da-aa69-476506cabe89
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroidal glycosides > Steroidal saponins > Cucurbitacin glycosides
• IUPAC Name: [(E,6R)-6-[(7R,8S,9S,10R,13R,14S,16R,17R)-7,16-dihydroxy-2-[(2S,3R,4S,5S)-4-hydroxy-5-[(2S,3R,4S,5S)-4-hydroxy-5-(hydroxymethyl)-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxolan-2-yl]oxy-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-4,4,9,13,14-pentamethyl-3,11-dioxo-8,10,12,15,16,17-hexahydro-7H-cyclopenta[a]phenanthren-17-yl]-6-hydroxy-2-methyl-5-oxohept-3-en-2-yl] acetate
• SMILES (Canonical): CC1C(C(C(C(O1)OC2C(C(COC2OC3=CC4C(=CC(C5C4(C(=O)CC6(C5(CC(C6C(C)(C(=O)C=CC(C)(C)OC(=O)C)O)O)C)C)C)O)C(C3=O)(C)C)OC7C(C(C(O7)CO)O)OC8C(C(C(C(O8)C)O)O)O)O)O)O)O
• SMILES (Isomeric): C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)O[C@@H]2[C@H]([C@H](CO[C@H]2OC3=C[C@@H]4C(=C[C@H]([C@@H]5[C@]4(C(=O)C[C@]6([C@]5(C[C@H]([C@@H]6[C@](C)(C(=O)/C=C/C(C)(C)OC(=O)C)O)O)C)C)C)O)C(C3=O)(C)C)O[C@H]7[C@@H]([C@H]([C@@H](O7)CO)O)O[C@H]8[C@@H]([C@@H]([C@H]([C@@H](O8)C)O)O)O)O)O)O)O
• InChI: InChI=1S/C54H80O25/c1-20-32(61)36(65)38(67)45(72-20)77-40-35(64)29(76-48-41(34(63)28(18-55)75-48)78-46-39(68)37(66)33(62)21(2)73-46)19-71-47(40)74-27-15-24-23(50(6,7)44(27)69)14-25(57)42-51(8)16-26(58)43(52(51,9)17-31(60)53(24,42)10)54(11,70)30(59)12-13-49(4,5)79-22(3)56/h12-15,20-21,24-26,28-29,32-43,45-48,55,57-58,61-68,70H,16-19H2,1-11H3/b13-12+/t20-,21-,24+,25+,26+,28-,29-,32-,33-,34-,35-,36+,37+,38+,39+,40+,41+,42-,43-,45-,46-,47-,48-,51-,52+,53+,54-/m0/s1
• InChI Key: IFGSTKBYVZGKSH-JARDLGJNSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₅₄H₈₀O₂₅
• Molecular Weight: 1129.20 g/mol
• Exact Mass: 1128.49886803 g/mol
• Topological Polar Surface Area (TPSA): 394.00 Ų
• XlogP: -2.80
• Atomic LogP (AlogP): -2.77
• H-Bond Acceptor: 25
• H-Bond Donor: 12
• Rotatable Bonds: 14

Synonyms

• (-)-Bacobitacin D

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8573	85.73%
Caco-2	-	0.8634	86.34%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	-	0.8143	81.43%
Subcellular localzation	Mitochondria	0.8327	83.27%
OATP2B1 inhibitior	-	0.8691	86.91%
OATP1B1 inhibitior	+	0.8086	80.86%
OATP1B3 inhibitior	+	0.8860	88.60%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	+	0.9535	95.35%
P-glycoprotein inhibitior	+	0.7446	74.46%
P-glycoprotein substrate	+	0.7118	71.18%
CYP3A4 substrate	+	0.7468	74.68%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8976	89.76%
CYP3A4 inhibition	-	0.8194	81.94%
CYP2C9 inhibition	-	0.8721	87.21%
CYP2C19 inhibition	-	0.9202	92.02%
CYP2D6 inhibition	-	0.9427	94.27%
CYP1A2 inhibition	-	0.9179	91.79%
CYP2C8 inhibition	+	0.7764	77.64%
CYP inhibitory promiscuity	-	0.9347	93.47%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.5107	51.07%
Eye corrosion	-	0.9887	98.87%
Eye irritation	-	0.8985	89.85%
Skin irritation	-	0.5786	57.86%
Skin corrosion	-	0.9405	94.05%
Ames mutagenesis	-	0.5300	53.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7165	71.65%
Micronuclear	-	0.7400	74.00%
Hepatotoxicity	-	0.6125	61.25%
skin sensitisation	-	0.8849	88.49%
Respiratory toxicity	+	0.7222	72.22%
Reproductive toxicity	+	0.9556	95.56%
Mitochondrial toxicity	+	0.5875	58.75%
Nephrotoxicity	-	0.8454	84.54%
Acute Oral Toxicity (c)	III	0.5237	52.37%
Estrogen receptor binding	+	0.7474	74.74%
Androgen receptor binding	+	0.7510	75.10%
Thyroid receptor binding	+	0.6764	67.64%
Glucocorticoid receptor binding	+	0.8126	81.26%
Aromatase binding	+	0.6142	61.42%
PPAR gamma	+	0.8146	81.46%
Honey bee toxicity	-	0.5752	57.52%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	+	0.5100	51.00%
Fish aquatic toxicity	+	0.9785	97.85%

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	99.72%	91.11%
CHEMBL1951	P21397	Monoamine oxidase A	98.79%	91.49%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	98.49%	85.14%
CHEMBL2581	P07339	Cathepsin D	97.75%	98.95%
CHEMBL1293294	P51151	Ras-related protein Rab-9A	94.60%	87.67%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.52%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	93.71%	94.45%
CHEMBL1293249	Q13887	Kruppel-like factor 5	93.55%	86.33%
CHEMBL1806	P11388	DNA topoisomerase II alpha	93.10%	89.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	91.50%	97.09%
CHEMBL1994	P08235	Mineralocorticoid receptor	87.69%	100.00%
CHEMBL1902	P62942	FK506-binding protein 1A	86.78%	97.05%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	85.30%	91.07%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	85.18%	95.56%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	84.83%	91.24%
CHEMBL3401	O75469	Pregnane X receptor	84.29%	94.73%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	83.26%	94.00%
CHEMBL218	P21554	Cannabinoid CB1 receptor	83.15%	96.61%
CHEMBL5608	Q16288	NT-3 growth factor receptor	82.91%	95.89%
CHEMBL4829	O00763	Acetyl-CoA carboxylase 2	82.34%	98.00%
CHEMBL2335	P42785	Lysosomal Pro-X carboxypeptidase	80.62%	100.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	80.58%	99.23%
CHEMBL3714130	P46095	G-protein coupled receptor 6	80.42%	97.36%
CHEMBL3060	Q9Y345	Glycine transporter 2	80.42%	99.17%
CHEMBL241	Q14432	Phosphodiesterase 3A	80.24%	92.94%

Plants that contains it

• Bacopa monnieri

Cross-Links

• PubChem: 162962173
• LOTUS: LTS0025107
• wikiData: Q105112142