(1S,4aS,7aS)-7-[[(1S,4aS,7aS)-7-[[(1S,4aS,7aS)-7-[[(1S,4aS,7aS)-7-(acetyloxymethyl)-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-4-carbonyl]oxymethyl]-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-4-carbonyl]oxymethyl]-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-4-carbonyl]oxymethyl]-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-4-carboxylic acid

Details

• Internal ID: 244655ac-a48b-4ac3-a75b-49e5bb284bbd
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Iridoid O-glycosides
• IUPAC Name: (1S,4aS,7aS)-7-[[(1S,4aS,7aS)-7-[[(1S,4aS,7aS)-7-[[(1S,4aS,7aS)-7-(acetyloxymethyl)-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-4-carbonyl]oxymethyl]-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-4-carbonyl]oxymethyl]-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-4-carbonyl]oxymethyl]-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-4-carboxylic acid
• SMILES (Canonical): CC(=O)OCC1=CCC2C1C(OC=C2C(=O)OCC3=CCC4C3C(OC=C4C(=O)OCC5=CCC6C5C(OC=C6C(=O)OCC7=CCC8C7C(OC=C8C(=O)O)OC9C(C(C(C(O9)CO)O)O)O)OC1C(C(C(C(O1)CO)O)O)O)OC1C(C(C(C(O1)CO)O)O)O)OC1C(C(C(C(O1)CO)O)O)O
• SMILES (Isomeric): CC(=O)OCC1=CC[C@H]2[C@@H]1[C@@H](OC=C2C(=O)OCC3=CC[C@H]4[C@@H]3[C@@H](OC=C4C(=O)OCC5=CC[C@H]6[C@@H]5[C@@H](OC=C6C(=O)OCC7=CC[C@H]8[C@@H]7[C@@H](OC=C8C(=O)O)O[C@H]9[C@@H]([C@H]([C@@H]([C@H](O9)CO)O)O)O)O[C@H]1[C@@H]([C@H]([C@@H]([C@H](O1)CO)O)O)O)O[C@H]1[C@@H]([C@H]([C@@H]([C@H](O1)CO)O)O)O)O[C@H]1[C@@H]([C@H]([C@@H]([C@H](O1)CO)O)O)O
• InChI: InChI=1S/C66H84O38/c1-22(71)89-14-23-3-7-28-32(19-94-60(40(23)28)102-64-52(81)48(77)44(73)36(11-68)98-64)56(86)91-16-25-5-9-30-34(21-96-62(42(25)30)104-66-54(83)50(79)46(75)38(13-70)100-66)58(88)92-17-26-4-8-29-33(20-95-61(41(26)29)103-65-53(82)49(78)45(74)37(12-69)99-65)57(87)90-15-24-2-6-27-31(55(84)85)18-93-59(39(24)27)101-63-51(80)47(76)43(72)35(10-67)97-63/h2-5,18-21,27-30,35-54,59-70,72-83H,6-17H2,1H3,(H,84,85)/t27-,28-,29-,30-,35-,36-,37-,38-,39-,40-,41-,42-,43-,44-,45-,46-,47+,48+,49+,50+,51-,52-,53-,54-,59+,60+,61+,62+,63+,64+,65+,66+/m1/s1
• InChI Key: SSFQHGWAEPVGIY-DJNZBPMRSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₆₆H₈₄O₃₈
• Molecular Weight: 1485.30 g/mol
• Exact Mass: 1484.4640582 g/mol
• Topological Polar Surface Area (TPSA): 577.00 Ų
• XlogP: -7.70
• Atomic LogP (AlogP): -7.26
• H-Bond Acceptor: 37
• H-Bond Donor: 17
• Rotatable Bonds: 24

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.5886	58.86%
Caco-2	-	0.8577	85.77%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	-	0.7571	75.71%
Subcellular localzation	Mitochondria	0.7932	79.32%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.7462	74.62%
OATP1B3 inhibitior	+	0.9612	96.12%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	+	0.9275	92.75%
P-glycoprotein inhibitior	+	0.7424	74.24%
P-glycoprotein substrate	-	0.8001	80.01%
CYP3A4 substrate	+	0.6115	61.15%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8876	88.76%
CYP3A4 inhibition	-	0.9626	96.26%
CYP2C9 inhibition	-	0.9248	92.48%
CYP2C19 inhibition	-	0.8808	88.08%
CYP2D6 inhibition	-	0.9211	92.11%
CYP1A2 inhibition	-	0.8612	86.12%
CYP2C8 inhibition	-	0.5844	58.44%
CYP inhibitory promiscuity	-	0.8863	88.63%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.7358	73.58%
Eye corrosion	-	0.9883	98.83%
Eye irritation	-	0.8968	89.68%
Skin irritation	-	0.7672	76.72%
Skin corrosion	-	0.9515	95.15%
Ames mutagenesis	-	0.6800	68.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7645	76.45%
Micronuclear	-	0.7700	77.00%
Hepatotoxicity	-	0.8199	81.99%
skin sensitisation	-	0.8951	89.51%
Respiratory toxicity	-	0.5556	55.56%
Reproductive toxicity	+	0.7333	73.33%
Mitochondrial toxicity	+	0.5750	57.50%
Nephrotoxicity	+	0.8315	83.15%
Acute Oral Toxicity (c)	III	0.4211	42.11%
Estrogen receptor binding	+	0.6945	69.45%
Androgen receptor binding	+	0.7610	76.10%
Thyroid receptor binding	+	0.6367	63.67%
Glucocorticoid receptor binding	+	0.7552	75.52%
Aromatase binding	+	0.6345	63.45%
PPAR gamma	+	0.7846	78.46%
Honey bee toxicity	-	0.7921	79.21%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.7750	77.50%
Fish aquatic toxicity	+	0.9366	93.66%

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	97.30%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	93.61%	91.11%
CHEMBL3060	Q9Y345	Glycine transporter 2	90.08%	99.17%
CHEMBL3401	O75469	Pregnane X receptor	88.99%	94.73%
CHEMBL2581	P07339	Cathepsin D	88.68%	98.95%
CHEMBL3137262	O60341	LSD1/CoREST complex	86.85%	97.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	84.85%	89.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	84.80%	86.33%
CHEMBL5255	O00206	Toll-like receptor 4	82.81%	92.50%
CHEMBL1811	P34995	Prostanoid EP1 receptor	82.64%	95.71%

Plants that contains it

• Eucommia ulmoides

Cross-Links

• PubChem: 14540388
• LOTUS: LTS0067223
• wikiData: Q105259641