(1S,4aS,7aS)-7-(hydroxymethyl)-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(1R,2'R,5S,11R,12R,15S)-2'-hydroxy-3-methyl-2'-propan-2-ylspiro[3-azatetracyclo[6.5.1.11,5.011,14]pentadec-8(14)-ene-15,5'-oxane]-12-carbonyl]oxymethyl]oxan-2-yl]oxy-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-4-carboxylic acid

Details

• Internal ID: 35971dc0-47c3-4a81-afcd-3ebe560ababb
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Iridoid O-glycosides
• IUPAC Name: (1S,4aS,7aS)-7-(hydroxymethyl)-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(1R,2'R,5S,11R,12R,15S)-2'-hydroxy-3-methyl-2'-propan-2-ylspiro[3-azatetracyclo[6.5.1.11,5.011,14]pentadec-8(14)-ene-15,5'-oxane]-12-carbonyl]oxymethyl]oxan-2-yl]oxy-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-4-carboxylic acid
• SMILES (Canonical): CC(C)C1(CCC2(CO1)C3CCC4=C5C2(CC(C5CC4)C(=O)OCC6C(C(C(C(O6)OC7C8C(CC=C8CO)C(=CO7)C(=O)O)O)O)O)CN(C3)C)O
• SMILES (Isomeric): CC(C)[C@]1(CC[C@]2(CO1)[C@@H]3CCC4=C5[C@@]2(C[C@H]([C@H]5CC4)C(=O)OC[C@@H]6[C@H]([C@@H]([C@H]([C@@H](O6)O[C@H]7[C@H]8[C@H](CC=C8CO)C(=CO7)C(=O)O)O)O)O)CN(C3)C)O
• InChI: InChI=1S/C39H55NO13/c1-19(2)39(48)11-10-37(18-51-39)22-7-4-20-5-9-24-25(12-38(37,29(20)24)17-40(3)13-22)34(47)49-16-27-30(42)31(43)32(44)36(52-27)53-35-28-21(14-41)6-8-23(28)26(15-50-35)33(45)46/h6,15,19,22-25,27-28,30-32,35-36,41-44,48H,4-5,7-14,16-18H2,1-3H3,(H,45,46)/t22-,23-,24-,25-,27-,28-,30-,31+,32-,35+,36+,37+,38-,39-/m1/s1
• InChI Key: LLOSAJLSLUXOSZ-VUVWKRRGSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₉H₅₅NO₁₃
• Molecular Weight: 745.90 g/mol
• Exact Mass: 745.36734081 g/mol
• Topological Polar Surface Area (TPSA): 205.00 Ų
• XlogP: -2.60
• Atomic LogP (AlogP): 1.44
• H-Bond Acceptor: 13
• H-Bond Donor: 6
• Rotatable Bonds: 8

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6288	62.88%
Caco-2	-	0.8743	87.43%
Blood Brain Barrier	+	0.5750	57.50%
Human oral bioavailability	-	0.7143	71.43%
Subcellular localzation	Mitochondria	0.5280	52.80%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8126	81.26%
OATP1B3 inhibitior	+	0.9182	91.82%
MATE1 inhibitior	-	0.9420	94.20%
OCT2 inhibitior	-	0.8000	80.00%
BSEP inhibitior	-	0.4677	46.77%
P-glycoprotein inhibitior	+	0.7349	73.49%
P-glycoprotein substrate	+	0.6985	69.85%
CYP3A4 substrate	+	0.7351	73.51%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8571	85.71%
CYP3A4 inhibition	-	0.8135	81.35%
CYP2C9 inhibition	-	0.8251	82.51%
CYP2C19 inhibition	-	0.8800	88.00%
CYP2D6 inhibition	-	0.9507	95.07%
CYP1A2 inhibition	-	0.8967	89.67%
CYP2C8 inhibition	+	0.6630	66.30%
CYP inhibitory promiscuity	-	0.9862	98.62%
UGT catelyzed	-	0.8000	80.00%
Carcinogenicity (binary)	-	0.8900	89.00%
Carcinogenicity (trinary)	Danger	0.4594	45.94%
Eye corrosion	-	0.9838	98.38%
Eye irritation	-	0.9155	91.55%
Skin irritation	-	0.7190	71.90%
Skin corrosion	-	0.9222	92.22%
Ames mutagenesis	-	0.6300	63.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4288	42.88%
Micronuclear	+	0.5100	51.00%
Hepatotoxicity	-	0.5924	59.24%
skin sensitisation	-	0.8513	85.13%
Respiratory toxicity	+	0.8111	81.11%
Reproductive toxicity	+	0.9667	96.67%
Mitochondrial toxicity	+	0.9125	91.25%
Nephrotoxicity	+	0.5764	57.64%
Acute Oral Toxicity (c)	III	0.5790	57.90%
Estrogen receptor binding	+	0.8495	84.95%
Androgen receptor binding	+	0.7414	74.14%
Thyroid receptor binding	-	0.5825	58.25%
Glucocorticoid receptor binding	+	0.6540	65.40%
Aromatase binding	+	0.6559	65.59%
PPAR gamma	+	0.7216	72.16%
Honey bee toxicity	-	0.7036	70.36%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.6500	65.00%
Fish aquatic toxicity	+	0.8239	82.39%

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	99.39%	96.09%
CHEMBL253	P34972	Cannabinoid CB2 receptor	99.18%	97.25%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	97.66%	94.62%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.30%	91.11%
CHEMBL2581	P07339	Cathepsin D	93.70%	98.95%
CHEMBL3137262	O60341	LSD1/CoREST complex	92.79%	97.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.94%	95.56%
CHEMBL218	P21554	Cannabinoid CB1 receptor	90.56%	96.61%
CHEMBL1821	P08173	Muscarinic acetylcholine receptor M4	90.07%	94.08%
CHEMBL1806	P11388	DNA topoisomerase II alpha	89.67%	89.00%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	89.04%	96.47%
CHEMBL5608	Q16288	NT-3 growth factor receptor	88.46%	95.89%
CHEMBL3359	P21462	Formyl peptide receptor 1	87.28%	93.56%
CHEMBL5255	O00206	Toll-like receptor 4	86.89%	92.50%
CHEMBL4227	P25090	Lipoxin A4 receptor	86.45%	100.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	86.39%	94.45%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	86.12%	99.23%
CHEMBL5028	O14672	ADAM10	85.91%	97.50%
CHEMBL226	P30542	Adenosine A1 receptor	85.12%	95.93%
CHEMBL1994	P08235	Mineralocorticoid receptor	85.02%	100.00%
CHEMBL340	P08684	Cytochrome P450 3A4	83.58%	91.19%
CHEMBL2514	O95665	Neurotensin receptor 2	81.53%	100.00%
CHEMBL1795139	Q8IU80	Transmembrane protease serine 6	81.09%	98.33%

Plants that contains it

• Daphniphyllum calycinum

Cross-Links

• PubChem: 163040395
• LOTUS: LTS0050685
• wikiData: Q105161745