[(1S,6S,7R,7aS)-6-acetyloxy-4-(acetyloxymethyl)spiro[6,7a-dihydro-1H-cyclopenta[c]pyran-7,2'-oxirane]-1-yl] 3-methylbutanoate

Details

• Internal ID: d4e2d73b-872c-4adc-ad22-9e434fc075e5
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Monoterpenoids > Iridoids and derivatives
• IUPAC Name: [(1S,6S,7R,7aS)-6-acetyloxy-4-(acetyloxymethyl)spiro[6,7a-dihydro-1H-cyclopenta[c]pyran-7,2'-oxirane]-1-yl] 3-methylbutanoate
• SMILES (Canonical): CC(C)CC(=O)OC1C2C(=CC(C23CO3)OC(=O)C)C(=CO1)COC(=O)C
• SMILES (Isomeric): CC(C)CC(=O)O[C@H]1[C@H]2C(=C[C@@H]([C@]23CO3)OC(=O)C)C(=CO1)COC(=O)C
• InChI: InChI=1S/C19H24O8/c1-10(2)5-16(22)27-18-17-14(13(8-24-18)7-23-11(3)20)6-15(26-12(4)21)19(17)9-25-19/h6,8,10,15,17-18H,5,7,9H2,1-4H3/t15-,17+,18-,19+/m0/s1
• InChI Key: OZYPVATWXAXGPT-WZGPROSRSA-N
• Popularity: 4 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₉H₂₄O₈
• Molecular Weight: 380.40 g/mol
• Exact Mass: 380.14711772 g/mol
• Topological Polar Surface Area (TPSA): 101.00 Ų
• XlogP: 0.50
• Atomic LogP (AlogP): 1.64
• H-Bond Acceptor: 8
• H-Bond Donor: 0
• Rotatable Bonds: 6

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9783	97.83%
Caco-2	+	0.5000	50.00%
Blood Brain Barrier	+	0.9250	92.50%
Human oral bioavailability	-	0.6714	67.14%
Subcellular localzation	Mitochondria	0.7332	73.32%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8528	85.28%
OATP1B3 inhibitior	+	0.9107	91.07%
MATE1 inhibitior	-	0.8400	84.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	+	0.7487	74.87%
P-glycoprotein inhibitior	+	0.6049	60.49%
P-glycoprotein substrate	-	0.6109	61.09%
CYP3A4 substrate	+	0.6275	62.75%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8669	86.69%
CYP3A4 inhibition	-	0.9201	92.01%
CYP2C9 inhibition	-	0.8317	83.17%
CYP2C19 inhibition	-	0.7739	77.39%
CYP2D6 inhibition	-	0.8906	89.06%
CYP1A2 inhibition	-	0.8070	80.70%
CYP2C8 inhibition	-	0.6146	61.46%
CYP inhibitory promiscuity	-	0.8523	85.23%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.8800	88.00%
Carcinogenicity (trinary)	Non-required	0.5511	55.11%
Eye corrosion	-	0.9693	96.93%
Eye irritation	-	0.8579	85.79%
Skin irritation	-	0.6952	69.52%
Skin corrosion	-	0.9185	91.85%
Ames mutagenesis	+	0.6200	62.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5667	56.67%
Micronuclear	-	0.5700	57.00%
Hepatotoxicity	-	0.5448	54.48%
skin sensitisation	-	0.5886	58.86%
Respiratory toxicity	-	0.5444	54.44%
Reproductive toxicity	+	0.5778	57.78%
Mitochondrial toxicity	+	0.5625	56.25%
Nephrotoxicity	+	0.6623	66.23%
Acute Oral Toxicity (c)	III	0.4983	49.83%
Estrogen receptor binding	+	0.6927	69.27%
Androgen receptor binding	+	0.5663	56.63%
Thyroid receptor binding	-	0.5116	51.16%
Glucocorticoid receptor binding	+	0.8538	85.38%
Aromatase binding	+	0.5203	52.03%
PPAR gamma	-	0.4831	48.31%
Honey bee toxicity	-	0.7889	78.89%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.6200	62.00%
Fish aquatic toxicity	+	0.8991	89.91%

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	97.05%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.78%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	91.15%	94.45%
CHEMBL2581	P07339	Cathepsin D	89.95%	98.95%
CHEMBL3137262	O60341	LSD1/CoREST complex	87.23%	97.09%
CHEMBL253	P34972	Cannabinoid CB2 receptor	84.32%	97.25%
CHEMBL3060	Q9Y345	Glycine transporter 2	82.10%	99.17%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	81.08%	91.07%
CHEMBL3401	O75469	Pregnane X receptor	80.46%	94.73%
CHEMBL340	P08684	Cytochrome P450 3A4	80.21%	91.19%

Plants that contains it

• Valeriana capensis
• Valeriana glechomifolia
• Valeriana microphylla
• Valeriana officinalis

Cross-Links

• PubChem: 101656903
• LOTUS: LTS0060301
• wikiData: Q104666946