(1S,4aS,5R,7aS)-1-[(2S,3R,4R,5S,6R)-5-[(1S,4aS,5R,7aS)-5-hydroxy-7-(methylsulfanylcarbonyloxymethyl)-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]oxy-3,4-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-5-hydroxy-7-(methylsulfanylcarbonyloxymethyl)-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-4-carboxylic acid

Details

• Internal ID: 061d10c8-010e-4cdf-a8b1-a1013e6ae5ec
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Iridoid O-glycosides
• IUPAC Name: (1S,4aS,5R,7aS)-1-[(2S,3R,4R,5S,6R)-5-[(1S,4aS,5R,7aS)-5-hydroxy-7-(methylsulfanylcarbonyloxymethyl)-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]oxy-3,4-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-5-hydroxy-7-(methylsulfanylcarbonyloxymethyl)-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-4-carboxylic acid
• SMILES (Canonical): CSC(=O)OCC1=CC(C2C1C(OC=C2C(=O)O)OC3C(C(C(C(O3)CO)OC(=O)C4=COC(C5C4C(C=C5COC(=O)SC)O)OC6C(C(C(C(O6)CO)O)O)O)O)O)O
• SMILES (Isomeric): CSC(=O)OCC1=C[C@H]([C@H]2[C@@H]1[C@@H](OC=C2C(=O)O)O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)OC(=O)C4=CO[C@H]([C@H]5[C@@H]4[C@@H](C=C5COC(=O)SC)O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O)O)O)O
• InChI: InChI=1S/C36H46O23S2/c1-60-35(49)53-7-11-3-15(39)21-13(29(46)47)9-51-31(19(11)21)59-34-27(45)25(43)28(18(6-38)56-34)57-30(48)14-10-52-32(58-33-26(44)24(42)23(41)17(5-37)55-33)20-12(4-16(40)22(14)20)8-54-36(50)61-2/h3-4,9-10,15-28,31-34,37-45H,5-8H2,1-2H3,(H,46,47)/t15-,16-,17-,18-,19-,20-,21+,22+,23-,24+,25-,26-,27-,28-,31+,32+,33+,34+/m1/s1
• InChI Key: OCXLLLWIXQZTLP-RIENXSNZSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₆H₄₆O₂₃S₂
• Molecular Weight: 910.90 g/mol
• Exact Mass: 910.18713006 g/mol
• Topological Polar Surface Area (TPSA): 404.00 Ų
• XlogP: -4.30
• Atomic LogP (AlogP): -3.20
• H-Bond Acceptor: 24
• H-Bond Donor: 10
• Rotatable Bonds: 13

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.5183	51.83%
Caco-2	-	0.8761	87.61%
Blood Brain Barrier	-	0.5000	50.00%
Human oral bioavailability	-	0.8571	85.71%
Subcellular localzation	Mitochondria	0.6642	66.42%
OATP2B1 inhibitior	-	0.7263	72.63%
OATP1B1 inhibitior	+	0.7590	75.90%
OATP1B3 inhibitior	+	0.9391	93.91%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	+	0.7987	79.87%
P-glycoprotein inhibitior	+	0.7234	72.34%
P-glycoprotein substrate	-	0.6950	69.50%
CYP3A4 substrate	+	0.6312	63.12%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8753	87.53%
CYP3A4 inhibition	-	0.7989	79.89%
CYP2C9 inhibition	-	0.8246	82.46%
CYP2C19 inhibition	-	0.7321	73.21%
CYP2D6 inhibition	-	0.8907	89.07%
CYP1A2 inhibition	-	0.8366	83.66%
CYP2C8 inhibition	+	0.5531	55.31%
CYP inhibitory promiscuity	-	0.6584	65.84%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6533	65.33%
Eye corrosion	-	0.9852	98.52%
Eye irritation	-	0.9070	90.70%
Skin irritation	-	0.7806	78.06%
Skin corrosion	-	0.9403	94.03%
Ames mutagenesis	-	0.6600	66.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7347	73.47%
Micronuclear	-	0.5400	54.00%
Hepatotoxicity	-	0.8000	80.00%
skin sensitisation	-	0.8473	84.73%
Respiratory toxicity	+	0.5889	58.89%
Reproductive toxicity	+	0.8111	81.11%
Mitochondrial toxicity	+	0.6875	68.75%
Nephrotoxicity	+	0.7613	76.13%
Acute Oral Toxicity (c)	III	0.5265	52.65%
Estrogen receptor binding	+	0.7963	79.63%
Androgen receptor binding	+	0.7016	70.16%
Thyroid receptor binding	-	0.4950	49.50%
Glucocorticoid receptor binding	+	0.6835	68.35%
Aromatase binding	+	0.5628	56.28%
PPAR gamma	+	0.7584	75.84%
Honey bee toxicity	-	0.6936	69.36%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.6650	66.50%
Fish aquatic toxicity	+	0.7878	78.78%

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	96.32%	96.09%
CHEMBL3060	Q9Y345	Glycine transporter 2	92.52%	99.17%
CHEMBL1293249	Q13887	Kruppel-like factor 5	91.39%	86.33%
CHEMBL3401	O75469	Pregnane X receptor	90.67%	94.73%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	87.62%	91.11%
CHEMBL3714130	P46095	G-protein coupled receptor 6	84.15%	97.36%
CHEMBL1811	P34995	Prostanoid EP1 receptor	83.84%	95.71%
CHEMBL1966	Q02127	Dihydroorotate dehydrogenase	82.75%	96.09%
CHEMBL5255	O00206	Toll-like receptor 4	82.42%	92.50%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	81.65%	95.56%

Plants that contains it

• Saprosma scortechinii

Cross-Links

• PubChem: 163029266
• LOTUS: LTS0034420
• wikiData: Q105189640