Acevaltrate

Details

• Internal ID: 814c4b16-29a4-4cca-ba72-595452986249
• Taxonomy: Organic acids and derivatives > Carboxylic acids and derivatives > Tetracarboxylic acids and derivatives
• IUPAC Name: [(1S,6S,7R,7aS)-4-(acetyloxymethyl)-1-(3-methylbutanoyloxy)spiro[6,7a-dihydro-1H-cyclopenta[c]pyran-7,2'-oxirane]-6-yl] 3-acetyloxy-3-methylbutanoate
• SMILES (Canonical): CC(C)CC(=O)OC1C2C(=CC(C23CO3)OC(=O)CC(C)(C)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)CC(C)(C)OC(=O)C)C(=CO1)COC(=O)C
• InChI: InChI=1S/C24H32O10/c1-13(2)7-19(27)33-22-21-17(16(11-30-22)10-29-14(3)25)8-18(24(21)12-31-24)32-20(28)9-23(5,6)34-15(4)26/h8,11,13,18,21-22H,7,9-10,12H2,1-6H3/t18-,21+,22-,24+/m0/s1
• InChI Key: FWKBQAVMKVZEOT-STCFVSJZSA-N
• Popularity: 78 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₄H₃₂O₁₀
• Molecular Weight: 480.50 g/mol
• Exact Mass: 480.19954721 g/mol
• Topological Polar Surface Area (TPSA): 127.00 Ų
• XlogP: 0.90
• Atomic LogP (AlogP): 2.35
• H-Bond Acceptor: 10
• H-Bond Donor: 0
• Rotatable Bonds: 9

Synonyms

• 25161-41-5
• Acevaltratum
• Acevaltrato
• S9MFK45GY9
• DTXSID30179834
• [(1S,6S,7R,7aS)-4-(acetyloxymethyl)-1-(3-methylbutanoyloxy)spiro[6,7a-dihydro-1H-cyclopenta[c]pyran-7,2'-oxirane]-6-yl] 3-acetyloxy-3-methylbutanoate
• ((1S,6S,7R,7aS)-4-(acetyloxymethyl)-1-(3-methylbutanoyloxy)spiro(6,7a-dihydro-1H-cyclopenta(c)pyran-7,2'-oxirane)-6-yl) 3-acetyloxy-3-methylbutanoate
• RefChem:109213
• GlyTouCan:G38217ZV
• DTXCID90102325
• G38217ZV
• 246-685-1
• (4-(acetyloxymethyl)-1-(3-methylbutanoyloxy)spiro(6,7a-dihydro-1H-cyclopenta(c)pyran-7,2'-oxirane)-6-yl) 3-acetyloxy-3-methylbutanoate
• 4-((acetyloxy)methyl)-7-((3-methylbutanoyl)oxy)-7,7a-dihydro-2H-spiro(cyclopenta(c)pyran-1,2'-oxirane)-2-yl 3-(acetyloxy)-3-methylbutanoate
• Acetoxyvaltrate
• Acevaltrate [INN]
• Acetovaltrate
• Butanoic acid, 3-(acetyloxy)-3-methyl-, (1S,2'R,6S,7aS)-4-[(acetyloxy)methyl]-6,7a-dihydro-1-(3-methyl-1-oxobutoxy)spiro[cyclopenta[c]pyran-7(1H),2'-oxiran]-6-yl ester
• (Acetyloxy)valepotriate
• Acevaltrat
• CHEBI:80704
• MFCD01741123
• 1,7a-Dihydro-1,6-dihydroxyspiro(cyclopenta(c)pyran-7(6H), 2'-oxirane)-4-methanol 4-acetate 1(or 6)-isovalerate 6(or 1)-(3-hydroxy-3-methylbutyrate, acetate)
• Acevaltrat [German]
• Acevaltratum [INN-Latin]
• Acevaltrato [INN-Spanish]
• EINECS 246-685-1
• C24H32O10
• UNII-S9MFK45GY9
• BUTANOIC ACID, 3-(ACETYLOXY)-3-METHYL-, (1S,2'R,6S,7AS)-4-((ACETYLOXY)METHYL)-6,7A-DIHYDRO-1-(3-METHYL-1-OXOBUTOXY)SPIRO(CYCLOPENTA(C)PYRAN-7(1H),2'-OXIRAN)-6-YL ESTER
• ACEVALTRATE [MART.]
• 1,7a-Dihydro-1,6-dihydroxyspiro(cyclopenta(c)pyran-7(6H),2-oxirane)-4-methanol 4-acetate 1(or 6)-isovalerate 6(or 1)-(3-hydroxy-3-methylbutyrate acetate
• 4-Acetoxymethyl-1,6,7,7a-tetrahydrocyclopenta(c)pyran-7-spiro-2'-oxiran-1,8-diyl 6-(beta-acetoxyisovalerat) 1-isovalerat oder 1-(beta-acetoxyisovalerat) 6-isovalerat
• CHEMBL563350
• orb1297691
• SCHEMBL2110695
• FWKBQAVMKVZEOT-STCFVSJZSA-N
• HY-N2070
• AKOS015896737
• FA74087
• Butanoic acid, 3-(acetyloxy)-3-methyl-, 4-((acetyloxy)methyl)-6,7a-dihydro-1-(3-methyl-1-oxobutoxy)spiro(cyclopenta(c)pyran-7(1H),2'-oxiran)-6-yl ester, (1S-(1-alpha,6-alpha,7-beta,7a-alpha))-
• DA-70514
• MS-28938
• CS-0018575
• NS00027821
• Q15633961
• (1S,6S,7R,7aS)-4-(Acetoxymethyl)-1-((3-methylbutanoyl)oxy)-6,7a-dihydro-1H-spiro[cyclopenta[c]pyran-7,2'-oxiran]-6-yl 3-acetoxy-3-methylbutanoate
• [(1S,6S,7R,7aS)-4-(acetoxymethyl)-1-(3-methylbutanoyloxy)spiro[6,7a-dihydro-1H-cyclopenta[c]pyran-7,2'-oxirane]-6-yl] 3-acetoxy-3-methyl-butanoate

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9748	97.48%
Caco-2	-	0.6832	68.32%
Blood Brain Barrier	+	0.9250	92.50%
Human oral bioavailability	-	0.6571	65.71%
Subcellular localzation	Mitochondria	0.7184	71.84%
OATP2B1 inhibitior	-	0.8589	85.89%
OATP1B1 inhibitior	+	0.8388	83.88%
OATP1B3 inhibitior	+	0.9024	90.24%
MATE1 inhibitior	-	0.8400	84.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	+	0.9526	95.26%
P-glycoprotein inhibitior	+	0.8083	80.83%
P-glycoprotein substrate	+	0.5587	55.87%
CYP3A4 substrate	+	0.6602	66.02%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8669	86.69%
CYP3A4 inhibition	-	0.8907	89.07%
CYP2C9 inhibition	-	0.8048	80.48%
CYP2C19 inhibition	-	0.7660	76.60%
CYP2D6 inhibition	-	0.9095	90.95%
CYP1A2 inhibition	-	0.7995	79.95%
CYP2C8 inhibition	+	0.5153	51.53%
CYP inhibitory promiscuity	-	0.8603	86.03%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.8800	88.00%
Carcinogenicity (trinary)	Non-required	0.5377	53.77%
Eye corrosion	-	0.9741	97.41%
Eye irritation	-	0.9280	92.80%
Skin irritation	-	0.6930	69.30%
Skin corrosion	-	0.9170	91.70%
Ames mutagenesis	+	0.5600	56.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6008	60.08%
Micronuclear	-	0.5700	57.00%
Hepatotoxicity	+	0.5749	57.49%
skin sensitisation	-	0.6124	61.24%
Respiratory toxicity	-	0.5333	53.33%
Reproductive toxicity	+	0.6000	60.00%
Mitochondrial toxicity	+	0.5750	57.50%
Nephrotoxicity	+	0.6498	64.98%
Acute Oral Toxicity (c)	III	0.5212	52.12%
Estrogen receptor binding	+	0.6907	69.07%
Androgen receptor binding	+	0.5951	59.51%
Thyroid receptor binding	+	0.5564	55.64%
Glucocorticoid receptor binding	+	0.8219	82.19%
Aromatase binding	+	0.5932	59.32%
PPAR gamma	+	0.6206	62.06%
Honey bee toxicity	-	0.7265	72.65%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.5600	56.00%
Fish aquatic toxicity	+	0.9022	90.22%

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	97.51%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.29%	91.11%
CHEMBL2581	P07339	Cathepsin D	94.80%	98.95%
CHEMBL253	P34972	Cannabinoid CB2 receptor	93.46%	97.25%
CHEMBL3137262	O60341	LSD1/CoREST complex	88.32%	97.09%
CHEMBL4051	P13569	Cystic fibrosis transmembrane conductance regulator	86.24%	95.71%
CHEMBL3060	Q9Y345	Glycine transporter 2	84.79%	99.17%
CHEMBL5966	P55899	IgG receptor FcRn large subunit p51	84.74%	90.93%
CHEMBL3401	O75469	Pregnane X receptor	83.58%	94.73%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	80.92%	95.56%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	80.85%	100.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	80.24%	94.45%

Plants that contains it

• Valeriana condamoana
• Valeriana eriophylla
• Valeriana glechomifolia
• Valeriana jatamansi
• Valeriana microphylla
• Valeriana micropterina
• Valeriana officinalis
• Valeriana pulvinata
• Valeriana rossica
• Valeriana sitchensis

Cross-Links

• PubChem: 65717
• NPASS: NPC90819
• ChEMBL: CHEMBL563350
• LOTUS: LTS0048028
• wikiData: Q15633961