(1S,4aS,7aS)-1-[(2S,3R,4S,5S,6R)-6-[[(1R,2S,3R,5R,6S,10S,16R,17R)-2,6-dimethyl-20-oxo-8-azahexacyclo[11.5.1.11,5.02,10.03,8.016,19]icos-13(19)-ene-17-carbonyl]oxymethyl]-3,4,5-trihydroxyoxan-2-yl]oxy-7-(hydroxymethyl)-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-4-carboxylic acid

Details

• Internal ID: 290b23fc-e4a2-45fa-ab6d-7836afd78854
• Taxonomy: Alkaloids and derivatives > Yuzurimine-type alkaloids
• IUPAC Name: (1S,4aS,7aS)-1-[(2S,3R,4S,5S,6R)-6-[[(1R,2S,3R,5R,6S,10S,16R,17R)-2,6-dimethyl-20-oxo-8-azahexacyclo[11.5.1.11,5.02,10.03,8.016,19]icos-13(19)-ene-17-carbonyl]oxymethyl]-3,4,5-trihydroxyoxan-2-yl]oxy-7-(hydroxymethyl)-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-4-carboxylic acid
• SMILES (Canonical): CC1CN2CC3CCC4=C5C(CC4)C(CC56C3(C2CC1C6=O)C)C(=O)OCC7C(C(C(C(O7)OC8C9C(CC=C9CO)C(=CO8)C(=O)O)O)O)O
• SMILES (Isomeric): C[C@@H]1CN2C[C@H]3CCC4=C5[C@H](CC4)[C@@H](C[C@]56[C@]3([C@H]2C[C@H]1C6=O)C)C(=O)OC[C@@H]7[C@H]([C@@H]([C@H]([C@@H](O7)O[C@H]8[C@H]9[C@H](CC=C9CO)C(=CO8)C(=O)O)O)O)O
• InChI: InChI=1S/C38H49NO12/c1-16-11-39-12-19-6-3-17-4-8-21-23(10-38(28(17)21)32(44)22(16)9-26(39)37(19,38)2)34(47)48-15-25-29(41)30(42)31(43)36(50-25)51-35-27-18(13-40)5-7-20(27)24(14-49-35)33(45)46/h5,14,16,19-23,25-27,29-31,35-36,40-43H,3-4,6-13,15H2,1-2H3,(H,45,46)/t16-,19-,20-,21-,22-,23-,25-,26-,27-,29-,30+,31-,35+,36+,37-,38+/m1/s1
• InChI Key: BGFSQHCTVLDZEX-QTLPULPNSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₈H₄₉NO₁₂
• Molecular Weight: 711.80 g/mol
• Exact Mass: 711.32547600 g/mol
• Topological Polar Surface Area (TPSA): 193.00 Ų
• XlogP: -2.80
• Atomic LogP (AlogP): 1.29
• H-Bond Acceptor: 12
• H-Bond Donor: 5
• Rotatable Bonds: 7

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7340	73.40%
Caco-2	-	0.8767	87.67%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	-	0.7143	71.43%
Subcellular localzation	Mitochondria	0.5860	58.60%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.7986	79.86%
OATP1B3 inhibitior	+	0.9354	93.54%
MATE1 inhibitior	-	0.9420	94.20%
OCT2 inhibitior	-	0.8021	80.21%
BSEP inhibitior	-	0.5968	59.68%
P-glycoprotein inhibitior	+	0.7081	70.81%
P-glycoprotein substrate	+	0.6448	64.48%
CYP3A4 substrate	+	0.7289	72.89%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8603	86.03%
CYP3A4 inhibition	-	0.9008	90.08%
CYP2C9 inhibition	-	0.9046	90.46%
CYP2C19 inhibition	-	0.9220	92.20%
CYP2D6 inhibition	-	0.9396	93.96%
CYP1A2 inhibition	-	0.9053	90.53%
CYP2C8 inhibition	+	0.7300	73.00%
CYP inhibitory promiscuity	-	0.9631	96.31%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Danger	0.5271	52.71%
Eye corrosion	-	0.9853	98.53%
Eye irritation	-	0.9184	91.84%
Skin irritation	-	0.7165	71.65%
Skin corrosion	-	0.9254	92.54%
Ames mutagenesis	-	0.6070	60.70%
Human Ether-a-go-go-Related Gene inhibition	-	0.3890	38.90%
Micronuclear	+	0.6200	62.00%
Hepatotoxicity	-	0.5750	57.50%
skin sensitisation	-	0.8597	85.97%
Respiratory toxicity	+	0.7000	70.00%
Reproductive toxicity	+	0.9556	95.56%
Mitochondrial toxicity	+	0.9250	92.50%
Nephrotoxicity	+	0.5435	54.35%
Acute Oral Toxicity (c)	III	0.5783	57.83%
Estrogen receptor binding	+	0.8222	82.22%
Androgen receptor binding	+	0.7614	76.14%
Thyroid receptor binding	-	0.5783	57.83%
Glucocorticoid receptor binding	+	0.6386	63.86%
Aromatase binding	+	0.6282	62.82%
PPAR gamma	+	0.6630	66.30%
Honey bee toxicity	-	0.7003	70.03%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.6100	61.00%
Fish aquatic toxicity	+	0.8966	89.66%

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	98.52%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	96.30%	97.09%
CHEMBL2581	P07339	Cathepsin D	96.01%	98.95%
CHEMBL5255	O00206	Toll-like receptor 4	94.32%	92.50%
CHEMBL253	P34972	Cannabinoid CB2 receptor	94.23%	97.25%
CHEMBL1293249	Q13887	Kruppel-like factor 5	92.63%	86.33%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	92.06%	91.11%
CHEMBL218	P21554	Cannabinoid CB1 receptor	89.41%	96.61%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	88.35%	94.62%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.08%	95.56%
CHEMBL340	P08684	Cytochrome P450 3A4	86.59%	91.19%
CHEMBL1806	P11388	DNA topoisomerase II alpha	86.50%	89.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	84.72%	99.23%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	83.96%	93.00%
CHEMBL1994	P08235	Mineralocorticoid receptor	83.03%	100.00%
CHEMBL3359	P21462	Formyl peptide receptor 1	82.75%	93.56%
CHEMBL1811	P34995	Prostanoid EP1 receptor	82.66%	95.71%
CHEMBL5028	O14672	ADAM10	82.08%	97.50%
CHEMBL2514	O95665	Neurotensin receptor 2	81.86%	100.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	81.12%	95.89%
CHEMBL1075162	Q13304	Uracil nucleotide/cysteinyl leukotriene receptor	81.03%	80.33%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	80.07%	91.71%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	80.01%	94.33%

Plants that contains it

• Daphniphyllum calycinum

Cross-Links

• PubChem: 21580235
• LOTUS: LTS0237503
• wikiData: Q104935500