(1S,4aS,7S,7aS)-1-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(E)-3-phenylprop-2-enoyl]oxyoxan-2-yl]oxy-7-hydroxy-7-methyl-4a,5,6,7a-tetrahydro-1H-cyclopenta[c]pyran-4-carboxylic acid

Details

• Internal ID: d2609686-7b54-4fdb-a269-f236665197ca
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Iridoid O-glycosides
• IUPAC Name: (1S,4aS,7S,7aS)-1-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(E)-3-phenylprop-2-enoyl]oxyoxan-2-yl]oxy-7-hydroxy-7-methyl-4a,5,6,7a-tetrahydro-1H-cyclopenta[c]pyran-4-carboxylic acid
• SMILES (Canonical): CC1(CCC2C1C(OC=C2C(=O)O)OC3C(C(C(C(O3)CO)O)O)OC(=O)C=CC4=CC=CC=C4)O
• SMILES (Isomeric): C[C@@]1(CC[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=CC=C4)O
• InChI: InChI=1S/C25H30O11/c1-25(32)10-9-14-15(22(30)31)12-33-23(18(14)25)36-24-21(20(29)19(28)16(11-26)34-24)35-17(27)8-7-13-5-3-2-4-6-13/h2-8,12,14,16,18-21,23-24,26,28-29,32H,9-11H2,1H3,(H,30,31)/b8-7+/t14-,16-,18-,19-,20+,21-,23+,24+,25+/m1/s1
• InChI Key: BIZBWPKKEHPFMI-GKBUEBNRSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₅H₃₀O₁₁
• Molecular Weight: 506.50 g/mol
• Exact Mass: 506.17881177 g/mol
• Topological Polar Surface Area (TPSA): 172.00 Ų
• XlogP: 0.70
• Atomic LogP (AlogP): 0.17
• H-Bond Acceptor: 10
• H-Bond Donor: 5
• Rotatable Bonds: 7

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7717	77.17%
Caco-2	-	0.8984	89.84%
Blood Brain Barrier	+	0.5500	55.00%
Human oral bioavailability	-	0.7857	78.57%
Subcellular localzation	Mitochondria	0.7427	74.27%
OATP2B1 inhibitior	-	0.8489	84.89%
OATP1B1 inhibitior	+	0.7359	73.59%
OATP1B3 inhibitior	+	0.9263	92.63%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.7183	71.83%
BSEP inhibitior	-	0.5815	58.15%
P-glycoprotein inhibitior	-	0.5709	57.09%
P-glycoprotein substrate	-	0.7081	70.81%
CYP3A4 substrate	+	0.6684	66.84%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8825	88.25%
CYP3A4 inhibition	-	0.8081	80.81%
CYP2C9 inhibition	-	0.8406	84.06%
CYP2C19 inhibition	-	0.8867	88.67%
CYP2D6 inhibition	-	0.9145	91.45%
CYP1A2 inhibition	-	0.8369	83.69%
CYP2C8 inhibition	+	0.7181	71.81%
CYP inhibitory promiscuity	-	0.8730	87.30%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6107	61.07%
Eye corrosion	-	0.9917	99.17%
Eye irritation	-	0.9461	94.61%
Skin irritation	-	0.5999	59.99%
Skin corrosion	-	0.9288	92.88%
Ames mutagenesis	-	0.6670	66.70%
Human Ether-a-go-go-Related Gene inhibition	-	0.4075	40.75%
Micronuclear	-	0.7500	75.00%
Hepatotoxicity	-	0.7941	79.41%
skin sensitisation	-	0.8885	88.85%
Respiratory toxicity	+	0.7333	73.33%
Reproductive toxicity	+	0.8889	88.89%
Mitochondrial toxicity	+	0.7500	75.00%
Nephrotoxicity	-	0.7942	79.42%
Acute Oral Toxicity (c)	III	0.4357	43.57%
Estrogen receptor binding	+	0.8021	80.21%
Androgen receptor binding	+	0.6282	62.82%
Thyroid receptor binding	+	0.5666	56.66%
Glucocorticoid receptor binding	+	0.6267	62.67%
Aromatase binding	+	0.6042	60.42%
PPAR gamma	+	0.6195	61.95%
Honey bee toxicity	-	0.8083	80.83%
Biodegradation	-	0.6250	62.50%
Crustacea aquatic toxicity	-	0.6200	62.00%
Fish aquatic toxicity	+	0.9061	90.61%

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	97.52%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.36%	96.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	96.24%	86.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	95.03%	95.56%
CHEMBL216	P11229	Muscarinic acetylcholine receptor M1	93.69%	94.23%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	93.61%	94.62%
CHEMBL3137262	O60341	LSD1/CoREST complex	93.37%	97.09%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	92.02%	96.00%
CHEMBL1821	P08173	Muscarinic acetylcholine receptor M4	91.99%	94.08%
CHEMBL221	P23219	Cyclooxygenase-1	91.36%	90.17%
CHEMBL1806	P11388	DNA topoisomerase II alpha	88.79%	89.00%
CHEMBL4208	P20618	Proteasome component C5	87.04%	90.00%
CHEMBL5028	O14672	ADAM10	86.78%	97.50%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	85.97%	93.00%
CHEMBL2581	P07339	Cathepsin D	85.37%	98.95%
CHEMBL4227	P25090	Lipoxin A4 receptor	83.97%	100.00%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	80.46%	96.95%
CHEMBL1994	P08235	Mineralocorticoid receptor	80.25%	100.00%

Plants that contains it

• Avicennia germinans
• Avicennia marina
• Avicennia officinalis
• Avicennia schaueriana

Cross-Links

• PubChem: 101919823
• LOTUS: LTS0087600
• wikiData: Q104392522