Valtrate

Details

• Internal ID: 4cb2d14a-05f3-4277-a785-03cd430bfb70
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Monoterpenoids > Iridoids 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-methylbutanoate
• SMILES (Canonical): CC(C)CC(=O)OC1C=C2C(C13CO3)C(OC=C2COC(=O)C)OC(=O)CC(C)C
• SMILES (Isomeric): CC(C)CC(=O)O[C@H]1C=C2[C@@H]([C@@]13CO3)[C@@H](OC=C2COC(=O)C)OC(=O)CC(C)C
• InChI: InChI=1S/C22H30O8/c1-12(2)6-18(24)29-17-8-16-15(9-26-14(5)23)10-27-21(20(16)22(17)11-28-22)30-19(25)7-13(3)4/h8,10,12-13,17,20-21H,6-7,9,11H2,1-5H3/t17-,20+,21-,22+/m0/s1
• InChI Key: BDIAUFOIMFAIPU-KVJIRVJXSA-N
• Popularity: 197 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

• Valepotriate
• 18296-44-1
• Valtratum
• Valtrato
• Valtrats
• Halazuchrome B
• Valtrate [INN]
• UNII-L3JQ035X9B
• Baldrisedon
• Valtrats [German]
• CCRIS 5795
• L3JQ035X9B
• Valtratum [INN-Latin]
• Valtrato [INN-Spanish]
• EINECS 242-174-2
• CHEBI:9928
• [(1S,6S,7R,7aS)-4-(acetyloxymethyl)-1-(3-methylbutanoyloxy)spiro[6,7a-dihydro-1H-cyclopenta[c]pyran-7,2'-oxirane]-6-yl] 3-methylbutanoate
• VALTRATE (MART.)
• VALTRATE [MART.]
• 4-Acetoxymethyl-1,6,7,7a-tetrahydro-1,6-bis(isovaleryloxy)cyclopenta(c)pyran-7-spiro-2'-oxiran
• (7S)-4-Acetoxymethyl-1,6,7,7a-tetrahydro-1alpha,6alpha-bis(isovaleroyl)cyclopent(c)pyran-7-spiro-2-oxiran
• 3a,4-Dihydro-3,4-dihydroxyspiro(benzofuran-2(3H),2'-oxirane)-6-methanol 6-acetate 3,4-diisovalerate
• Butanoic acid, 3-methyl-, 4-((acetyloxy)methyl)-6,7a-dihydrospiro(cyclopenta(c)pyran-7(1H),2'-oxirane)-1,6-diyl ester, (1S-(1-alpha,6-alpha,7-beta,7a-alpha))-
• VALTRATE [WHO-DD]
• CHEMBL402061
• MEGxp0_000900
• SCHEMBL1073699
• ACon0_000478
• BDIAUFOIMFAIPU-KVJIRVJXSA-N
• DTXSID501031053
• 1,7a-Dihydro-1,6-dihydroxyspiro(cyclopenta(c)pyran-7-(6H),2'-oxirane)-4-methanol 4-acetate 1,6-diisovalerate
• Butanoic acid, 3-methyl-, 4-[(acetyloxy)methyl]-6,7a-dihydrospiro[cyclopenta[c]pyran-7(1H),2'-oxirane]-1,6-diyl ester, [1S-(1.alpha.,6.alpha.,7.beta.,7a.alpha.)]-
• HY-N0718
• MFCD00868024
• AKOS015896850
• LMPR0102070015
• AC-34887
• MS-27416
• CS-0009735
• C09801
• V-2700
• Q27108520
• (1S,2'R,6S)-4-(acetoxymethyl)-6,7a-dihydro-1H-spiro[cyclopenta[c]pyran-7,2'-oxirane]-1,6-diyl bis(3-methylbutanoate)
• (1S,6S,7R,7aS)-4-[(Acetyloxy)methyl]-6,7a-dihydro-1H-spiro[cyclopenta[c]pyran-7,2'-oxirane]-1,6-diyl bis(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-methylbutanoate
• Butanoic acid, 3-methyl-, 1,1'-[(1S,2'R,6S,7aS)-4-[(acetyloxy)methyl]-6,7a-dihydrospiro[cyclopenta[c]pyran-7(1H),2'-oxirane]-1,6-diyl] ester
• Butanoic acid, 3-methyl-, 4-((acetyloxy)methyl)-6,7a-dihydrospiro(cyclopenta(c)pyran-7(1H),2'-oxirane)-1,6-diyl ester, (1S-(1alpha,6alpha,7beta,7aalpha))-
• BUTANOIC ACID, 3-METHYL-, 4-((ACETYLOXY)METHYL)-6,7A-DIHYDROSPIRO(CYCLOPENTA-(C)PYRAN-7(1H),2'-OXIRANE)-1,6-DIYL ESTER, (1S-(1-.ALPHA.,6-.ALPHA,,7- .BETA.,7A-.ALPHA.))-
• BUTANOIC ACID, 3-METHYL-, 4-((ACETYLOXY)METHYL)-6,7A-DIHYDROSPIRO(CYCLOPENTA-(C)PYRAN-7(1H),2'-OXIRANE)-1,6-DIYL ESTER, (1S-(1-alpha,6-.ALPHA,,7-beta,7A-alpha))-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9783	97.83%
Caco-2	-	0.5730	57.30%
Blood Brain Barrier	+	0.9250	92.50%
Human oral bioavailability	-	0.6429	64.29%
Subcellular localzation	Mitochondria	0.7332	73.32%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8451	84.51%
OATP1B3 inhibitior	+	0.9107	91.07%
MATE1 inhibitior	-	0.8400	84.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	+	0.8489	84.89%
P-glycoprotein inhibitior	+	0.6999	69.99%
P-glycoprotein substrate	-	0.6277	62.77%
CYP3A4 substrate	+	0.6189	61.89%
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	-	0.6466	64.66%
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	-	0.9249	92.49%
Skin irritation	-	0.6952	69.52%
Skin corrosion	-	0.9185	91.85%
Ames mutagenesis	+	0.6000	60.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6248	62.48%
Micronuclear	-	0.5700	57.00%
Hepatotoxicity	+	0.5749	57.49%
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	+	0.6872	68.72%
Acute Oral Toxicity (c)	III	0.4983	49.83%
Estrogen receptor binding	+	0.6968	69.68%
Androgen receptor binding	+	0.5887	58.87%
Thyroid receptor binding	-	0.5711	57.11%
Glucocorticoid receptor binding	+	0.7789	77.89%
Aromatase binding	+	0.6035	60.35%
PPAR gamma	+	0.5329	53.29%
Honey bee toxicity	-	0.7762	77.62%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.6000	60.00%
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	96.40%	91.11%
CHEMBL2581	P07339	Cathepsin D	90.44%	98.95%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	89.98%	94.45%
CHEMBL3137262	O60341	LSD1/CoREST complex	86.67%	97.09%
CHEMBL253	P34972	Cannabinoid CB2 receptor	83.93%	97.25%
CHEMBL3060	Q9Y345	Glycine transporter 2	82.04%	99.17%
CHEMBL3401	O75469	Pregnane X receptor	81.46%	94.73%
CHEMBL340	P08684	Cytochrome P450 3A4	80.04%	91.19%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	80.02%	91.07%

Plants that contains it

• Jasminum polyanthum
• Valeriana ajanensis subsp. fasciculata
• Valeriana capensis
• Valeriana edulis
• Valeriana eriophylla
• Valeriana fedtschenkoi
• Valeriana glechomifolia
• Valeriana jatamansi
• Valeriana microphylla
• Valeriana micropterina
• Valeriana officinalis
• Valeriana prionophylla
• Valeriana pulvinata
• Valeriana rossica
• Valeriana sitchensis
• Valeriana sorbifolia
• Valeriana vaginata
• Valeriana wolgensis

Cross-Links

• PubChem: 442436
• NPASS: NPC241407
• ChEMBL: CHEMBL402061
• LOTUS: LTS0134617
• wikiData: Q105382468