(1R,4aR,7aR)-7-(hydroxymethyl)-1-[(2R,3S,4R,5R,6S)-3,4,5-trihydroxy-6-[[(1S,2'R,5R,11S,12S,15S)-2'-methoxy-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: 3aeb6636-2d11-4403-9577-5a71b730a50c
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Iridoid O-glycosides
• IUPAC Name: (1R,4aR,7aR)-7-(hydroxymethyl)-1-[(2R,3S,4R,5R,6S)-3,4,5-trihydroxy-6-[[(1S,2'R,5R,11S,12S,15S)-2'-methoxy-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)OC
• 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)OC
• InChI: InChI=1S/C40H57NO13/c1-20(2)40(49-4)12-11-38(19-52-40)23-8-5-21-6-10-25-26(13-39(38,30(21)25)18-41(3)14-23)35(48)50-17-28-31(43)32(44)33(45)37(53-28)54-36-29-22(15-42)7-9-24(29)27(16-51-36)34(46)47/h7,16,20,23-26,28-29,31-33,36-37,42-45H,5-6,8-15,17-19H2,1-4H3,(H,46,47)/t23-,24-,25-,26-,28-,29-,31-,32+,33-,36+,37+,38-,39-,40+/m0/s1
• InChI Key: JAFMBIXBRHZIQZ-RGFXABRPSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₄₀H₅₇NO₁₃
• Molecular Weight: 759.90 g/mol
• Exact Mass: 759.38299087 g/mol
• Topological Polar Surface Area (TPSA): 194.00 Ų
• XlogP: -2.10
• Atomic LogP (AlogP): 2.10
• H-Bond Acceptor: 13
• H-Bond Donor: 5
• Rotatable Bonds: 9

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.4709	47.09%
Caco-2	-	0.8718	87.18%
Blood Brain Barrier	+	0.5500	55.00%
Human oral bioavailability	-	0.7143	71.43%
Subcellular localzation	Mitochondria	0.5980	59.80%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8086	80.86%
OATP1B3 inhibitior	+	0.9082	90.82%
MATE1 inhibitior	-	0.9420	94.20%
OCT2 inhibitior	-	0.7750	77.50%
BSEP inhibitior	+	0.5994	59.94%
P-glycoprotein inhibitior	+	0.7414	74.14%
P-glycoprotein substrate	+	0.7182	71.82%
CYP3A4 substrate	+	0.7382	73.82%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8580	85.80%
CYP3A4 inhibition	-	0.8659	86.59%
CYP2C9 inhibition	-	0.8320	83.20%
CYP2C19 inhibition	-	0.8811	88.11%
CYP2D6 inhibition	-	0.9510	95.10%
CYP1A2 inhibition	-	0.8871	88.71%
CYP2C8 inhibition	+	0.6986	69.86%
CYP inhibitory promiscuity	-	0.9769	97.69%
UGT catelyzed	-	0.8000	80.00%
Carcinogenicity (binary)	-	0.8800	88.00%
Carcinogenicity (trinary)	Danger	0.4551	45.51%
Eye corrosion	-	0.9837	98.37%
Eye irritation	-	0.9144	91.44%
Skin irritation	-	0.7292	72.92%
Skin corrosion	-	0.9224	92.24%
Ames mutagenesis	-	0.6070	60.70%
Human Ether-a-go-go-Related Gene inhibition	-	0.4303	43.03%
Micronuclear	+	0.5100	51.00%
Hepatotoxicity	-	0.6248	62.48%
skin sensitisation	-	0.8535	85.35%
Respiratory toxicity	+	0.8000	80.00%
Reproductive toxicity	+	0.9556	95.56%
Mitochondrial toxicity	+	0.9250	92.50%
Nephrotoxicity	+	0.5715	57.15%
Acute Oral Toxicity (c)	III	0.6167	61.67%
Estrogen receptor binding	+	0.8487	84.87%
Androgen receptor binding	+	0.7463	74.63%
Thyroid receptor binding	-	0.5738	57.38%
Glucocorticoid receptor binding	+	0.6808	68.08%
Aromatase binding	+	0.6708	67.08%
PPAR gamma	+	0.7426	74.26%
Honey bee toxicity	-	0.6809	68.09%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.6400	64.00%
Fish aquatic toxicity	+	0.8710	87.10%

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	99.44%	96.09%
CHEMBL253	P34972	Cannabinoid CB2 receptor	99.32%	97.25%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.48%	91.11%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	96.82%	94.62%
CHEMBL2581	P07339	Cathepsin D	95.61%	98.95%
CHEMBL3137262	O60341	LSD1/CoREST complex	92.10%	97.09%
CHEMBL1821	P08173	Muscarinic acetylcholine receptor M4	91.93%	94.08%
CHEMBL218	P21554	Cannabinoid CB1 receptor	91.15%	96.61%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.54%	95.56%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	89.33%	96.47%
CHEMBL5608	Q16288	NT-3 growth factor receptor	87.42%	95.89%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	87.13%	94.45%
CHEMBL1806	P11388	DNA topoisomerase II alpha	87.09%	89.00%
CHEMBL5028	O14672	ADAM10	86.41%	97.50%
CHEMBL4227	P25090	Lipoxin A4 receptor	86.04%	100.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	85.52%	99.23%
CHEMBL5255	O00206	Toll-like receptor 4	85.50%	92.50%
CHEMBL340	P08684	Cytochrome P450 3A4	85.27%	91.19%
CHEMBL3359	P21462	Formyl peptide receptor 1	85.14%	93.56%
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	83.18%	95.17%
CHEMBL1994	P08235	Mineralocorticoid receptor	82.92%	100.00%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	81.92%	93.00%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	80.57%	97.14%
CHEMBL1795139	Q8IU80	Transmembrane protease serine 6	80.31%	98.33%

Plants that contains it

• Daphniphyllum calycinum

Cross-Links

• PubChem: 163048457
• LOTUS: LTS0174660
• wikiData: Q105123733