(1S,4aS,6S,7R,7aS)-1-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-3-[(E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy-6-(hydroxymethyl)oxan-2-yl]oxy-6-hydroxy-7-methyl-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-4-carboxylic acid

Details

• Internal ID: 036ba54a-da61-4453-93a1-486f289fbb92
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Iridoid O-glycosides
• IUPAC Name: (1S,4aS,6S,7R,7aS)-1-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-3-[(E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy-6-(hydroxymethyl)oxan-2-yl]oxy-6-hydroxy-7-methyl-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-4-carboxylic acid
• SMILES (Canonical): CC1C(CC2C1C(OC=C2C(=O)O)OC3C(C(C(C(O3)CO)O)O)OC(=O)C=CC4=CC(=C(C=C4)O)OC)O
• SMILES (Isomeric): C[C@H]1[C@H](C[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)O)O)OC(=O)/C=C/C4=CC(=C(C=C4)O)OC)O
• InChI: InChI=1S/C26H32O13/c1-11-16(29)8-13-14(24(33)34)10-36-25(20(11)13)39-26-23(22(32)21(31)18(9-27)37-26)38-19(30)6-4-12-3-5-15(28)17(7-12)35-2/h3-7,10-11,13,16,18,20-23,25-29,31-32H,8-9H2,1-2H3,(H,33,34)/b6-4+/t11-,13+,16-,18+,20+,21+,22-,23+,25-,26-/m0/s1
• InChI Key: GALCALDKJPMULI-QZRLTIIASA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₆H₃₂O₁₃
• Molecular Weight: 552.50 g/mol
• Exact Mass: 552.18429107 g/mol
• Topological Polar Surface Area (TPSA): 202.00 Ų
• XlogP: 0.60
• Atomic LogP (AlogP): -0.26
• H-Bond Acceptor: 12
• 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	+	0.8072	80.72%
Caco-2	-	0.8891	88.91%
Blood Brain Barrier	-	0.6000	60.00%
Human oral bioavailability	-	0.7714	77.14%
Subcellular localzation	Mitochondria	0.4794	47.94%
OATP2B1 inhibitior	-	0.8601	86.01%
OATP1B1 inhibitior	-	0.3612	36.12%
OATP1B3 inhibitior	+	0.9579	95.79%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	-	0.5091	50.91%
P-glycoprotein inhibitior	-	0.6037	60.37%
P-glycoprotein substrate	-	0.5388	53.88%
CYP3A4 substrate	+	0.6547	65.47%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8699	86.99%
CYP3A4 inhibition	-	0.8254	82.54%
CYP2C9 inhibition	-	0.8173	81.73%
CYP2C19 inhibition	-	0.8468	84.68%
CYP2D6 inhibition	-	0.8589	85.89%
CYP1A2 inhibition	-	0.7495	74.95%
CYP2C8 inhibition	+	0.7131	71.31%
CYP inhibitory promiscuity	-	0.8092	80.92%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.7206	72.06%
Eye corrosion	-	0.9902	99.02%
Eye irritation	-	0.9355	93.55%
Skin irritation	-	0.7615	76.15%
Skin corrosion	-	0.9426	94.26%
Ames mutagenesis	-	0.5623	56.23%
Human Ether-a-go-go-Related Gene inhibition	+	0.6923	69.23%
Micronuclear	-	0.5600	56.00%
Hepatotoxicity	-	0.7216	72.16%
skin sensitisation	-	0.8292	82.92%
Respiratory toxicity	+	0.7556	75.56%
Reproductive toxicity	+	0.9667	96.67%
Mitochondrial toxicity	+	0.7625	76.25%
Nephrotoxicity	-	0.9713	97.13%
Acute Oral Toxicity (c)	III	0.4756	47.56%
Estrogen receptor binding	+	0.8135	81.35%
Androgen receptor binding	+	0.5434	54.34%
Thyroid receptor binding	+	0.5326	53.26%
Glucocorticoid receptor binding	+	0.6072	60.72%
Aromatase binding	-	0.5596	55.96%
PPAR gamma	+	0.6396	63.96%
Honey bee toxicity	-	0.7753	77.53%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.6700	67.00%
Fish aquatic toxicity	+	0.8995	89.95%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	99.51%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.20%	96.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	96.56%	86.33%
CHEMBL1806	P11388	DNA topoisomerase II alpha	96.55%	89.00%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	96.47%	96.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	94.64%	95.56%
CHEMBL3137262	O60341	LSD1/CoREST complex	93.46%	97.09%
CHEMBL1951	P21397	Monoamine oxidase A	93.26%	91.49%
CHEMBL4208	P20618	Proteasome component C5	93.04%	90.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	91.92%	99.17%
CHEMBL3194	P02766	Transthyretin	91.91%	90.71%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	89.08%	89.62%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	87.44%	95.50%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	87.37%	86.92%
CHEMBL3401	O75469	Pregnane X receptor	87.15%	94.73%

Plants that contains it

• Celastrus angulata
• Chiococca alba
• Tripterygium wilfordii

Cross-Links

• PubChem: 10578625
• LOTUS: LTS0109888
• wikiData: Q105226638