Isovaltrate

Details

• Internal ID: 617518da-36dd-4bad-ac6c-dba0e1aa40ea
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Monoterpenoids > Iridoids and derivatives
• IUPAC Name: [(1S,6S,7R,7aS)-6-acetyloxy-1-(3-methylbutanoyloxy)spiro[6,7a-dihydro-1H-cyclopenta[c]pyran-7,2'-oxirane]-4-yl]methyl 3-methylbutanoate
• SMILES (Canonical): CC(C)CC(=O)OCC1=COC(C2C1=CC(C23CO3)OC(=O)C)OC(=O)CC(C)C
• SMILES (Isomeric): CC(C)CC(=O)OCC1=CO[C@H]([C@H]2C1=C[C@@H]([C@]23CO3)OC(=O)C)OC(=O)CC(C)C
• InChI: InChI=1S/C22H30O8/c1-12(2)6-18(24)26-9-15-10-27-21(30-19(25)7-13(3)4)20-16(15)8-17(29-14(5)23)22(20)11-28-22/h8,10,12-13,17,20-21H,6-7,9,11H2,1-5H3/t17-,20+,21-,22+/m0/s1
• InChI Key: XLACUABANMZLCJ-KVJIRVJXSA-N
• Popularity: 26 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₂H₃₀O₈
• Molecular Weight: 422.50 g/mol
• Exact Mass: 422.19406791 g/mol
• Topological Polar Surface Area (TPSA): 101.00 Ų
• XlogP: 1.80
• Atomic LogP (AlogP): 2.66
• H-Bond Acceptor: 8
• H-Bond Donor: 0
• Rotatable Bonds: 8

Synonyms

• 31078-10-1
• EINECS 250-454-0
• CHEBI:80745
• (1S-(1alpha,6alpha,7beta,7aalpha))-6-Acetoxy-6,7a-dihydro-4-((isovaleryloxy)methyl)spiro(cyclopenta(c)pyran-7(1H),2'-oxiran)-1-yl isovalerate
• ((1S,2'R,6S,7aS)-6-Acetoxy-1-((3-methylbutanoyl)oxy)-6,7a-dihydro-1H-spiro[cyclopenta[c]pyran-7,2'-oxiran]-4-yl)methyl 3-methylbutanoate
• [1S-(1alpha,6alpha,7beta,7aalpha)]-6-acetoxy-6,7a-dihydro-4-[(isovaleryloxy)methyl]spiro[cyclopenta[c]pyran-7(1H),2'-oxiran]-1-yl isovalerate
• Isovaltrate/valtrate
• CHEMBL249657
• DTXSID80185026
• [(1S,6S,7R,7aS)-6-acetyloxy-1-(3-methylbutanoyloxy)spiro[6,7a-dihydro-1H-cyclopenta[c]pyran-7,2'-oxirane]-4-yl]methyl 3-methylbutanoate
• LS-46345
• Q27149798
• Butanoic acid, 3-methyl-, 6-(acetyloxy)-6,7a-dihydro-4-((3-methyl-1-oxobutoxy)methyl)spiro(cyclopenta(c)pyran-7(1H),2'-oxiran)-1-yl ester, (1S-(1alpha,6alpha,7beta,7aalpha))-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9686	96.86%
Caco-2	-	0.5800	58.00%
Blood Brain Barrier	+	0.9250	92.50%
Human oral bioavailability	-	0.7000	70.00%
Subcellular localzation	Mitochondria	0.7877	78.77%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8576	85.76%
OATP1B3 inhibitior	+	0.9275	92.75%
MATE1 inhibitior	-	0.8400	84.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	+	0.7374	73.74%
P-glycoprotein inhibitior	+	0.6330	63.30%
P-glycoprotein substrate	-	0.6199	61.99%
CYP3A4 substrate	+	0.6287	62.87%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8669	86.69%
CYP3A4 inhibition	-	0.8887	88.87%
CYP2C9 inhibition	-	0.8073	80.73%
CYP2C19 inhibition	-	0.7639	76.39%
CYP2D6 inhibition	-	0.8975	89.75%
CYP1A2 inhibition	-	0.8400	84.00%
CYP2C8 inhibition	-	0.5897	58.97%
CYP inhibitory promiscuity	-	0.8128	81.28%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.8800	88.00%
Carcinogenicity (trinary)	Non-required	0.4944	49.44%
Eye corrosion	-	0.9654	96.54%
Eye irritation	-	0.8758	87.58%
Skin irritation	-	0.7160	71.60%
Skin corrosion	-	0.9214	92.14%
Ames mutagenesis	+	0.6300	63.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4195	41.95%
Micronuclear	-	0.5700	57.00%
Hepatotoxicity	-	0.5448	54.48%
skin sensitisation	-	0.5931	59.31%
Respiratory toxicity	-	0.5111	51.11%
Reproductive toxicity	+	0.5667	56.67%
Mitochondrial toxicity	+	0.6500	65.00%
Nephrotoxicity	+	0.5933	59.33%
Acute Oral Toxicity (c)	III	0.5478	54.78%
Estrogen receptor binding	+	0.6901	69.01%
Androgen receptor binding	+	0.5519	55.19%
Thyroid receptor binding	-	0.5167	51.67%
Glucocorticoid receptor binding	+	0.8213	82.13%
Aromatase binding	+	0.6178	61.78%
PPAR gamma	+	0.5638	56.38%
Honey bee toxicity	-	0.7861	78.61%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.6400	64.00%
Fish aquatic toxicity	+	0.9230	92.30%

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	97.36%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.63%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	90.32%	94.45%
CHEMBL2581	P07339	Cathepsin D	90.26%	98.95%
CHEMBL3137262	O60341	LSD1/CoREST complex	87.33%	97.09%
CHEMBL2996	Q05655	Protein kinase C delta	82.86%	97.79%
CHEMBL3060	Q9Y345	Glycine transporter 2	81.38%	99.17%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	80.84%	95.89%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	80.68%	91.07%
CHEMBL3401	O75469	Pregnane X receptor	80.30%	94.73%
CHEMBL340	P08684	Cytochrome P450 3A4	80.21%	91.19%

Plants that contains it

• Valeriana capensis
• Valeriana edulis
• Valeriana eriophylla
• Valeriana jatamansi
• Valeriana microphylla
• Valeriana micropterina
• Valeriana officinalis
• Valeriana pulvinata
• Valeriana sitchensis
• Valeriana sorbifolia
• Valeriana vaginata

Cross-Links

• PubChem: 92275
• NPASS: NPC291709
• ChEMBL: CHEMBL249657
• LOTUS: LTS0042859
• wikiData: Q27149798