Didrovaltrate

Details

• Internal ID: 6c314979-ad16-4d50-baa4-3e30220de904
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Monoterpenoids > Iridoids and derivatives
• IUPAC Name: [(1S,4aS,6S,7R,7aS)-6-acetyloxy-1-(3-methylbutanoyloxy)spiro[4a,5,6,7a-tetrahydro-1H-cyclopenta[c]pyran-7,2'-oxirane]-4-yl]methyl 3-methylbutanoate
• SMILES (Canonical): CC(C)CC(=O)OCC1=COC(C2C1CC(C23CO3)OC(=O)C)OC(=O)CC(C)C
• SMILES (Isomeric): CC(C)CC(=O)OCC1=CO[C@H]([C@H]2[C@@H]1C[C@@H]([C@]23CO3)OC(=O)C)OC(=O)CC(C)C
• InChI: InChI=1S/C22H32O8/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/h10,12-13,16-17,20-21H,6-9,11H2,1-5H3/t16-,17+,20-,21+,22-/m1/s1
• InChI Key: PHHROXLDZHUIGO-PNBTUHDLSA-N
• Popularity: 90 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₂H₃₂O₈
• Molecular Weight: 424.50 g/mol
• Exact Mass: 424.20971797 g/mol
• Topological Polar Surface Area (TPSA): 101.00 Ų
• XlogP: 2.30
• Atomic LogP (AlogP): 2.74
• H-Bond Acceptor: 8
• H-Bond Donor: 0
• Rotatable Bonds: 8

Synonyms

• Didrovaltratum
• 18296-45-2
• Dihydroisovaltrate
• Isovaltrate, dihydro-
• Dihydroisovaltratum
• Isovalepotriate, dihydro-
• Dihydroisovalepotriate
• Didrovaltrat
• Didrovaltrato
• Dihydrovaltrate
• Didrovaltrate [INN]
• Isovaltrate, 4a,5-dihydro-
• Didrovaltrat [German]
• CCRIS 2662
• Didrovaltratum [INN-Latin]
• EINECS 242-175-8
• UNII-KEN63D125F
• Didrovaltrato [INN-Spanish]
• NSC 335756
• NSC-335756
• BRN 6010565
• KEN63D125F
• CHEBI:4517
• DTXSID80171363
• (7S)-6alpha-Acetoxy-1-alpha-isovaleryloxy-4-isovaleryloxymethyl-1,4aalpha,5,6,7,7aalpha-hexahydrocyclopenta(c)pyran-7-spiro-2'-oxiran
• 1,4a,5,7a-Tetrahydro-1,6-dihydroxyspiro(cyclopenta(c)pyran-7(6H),2'-oxirane)-4-methanol 6-acetate 1,4-diisovalerate
• Butanoic acid, 3-methyl-, (1S,4aS,6S,2'R,7aS)-6-(acetyloxy)-4a,5,6,7a-tetrahydro-4-((3-methyl-1-oxobutoxy)methyl)spiro(cyclopenta(c)pyran-7(1H),2'-oxiran)-1-yl ester
• Butanoic acid, 3-methyl-, 6-(acetyloxy)-4a,5,6,7a-tetrahydro-4-((3-methyl-1-oxobutoxy)methyl)spiro(cyclopenta(c)pyran-7(1H),2'-oxiran)-1-yl ester, (1S-(1-alpha,4a-alpha,6-alpha,7-beta,7a-alpha))-
• Isovaleric acid, 3,4-diester with 3a,4,5,6-tetrahydro-6-(hydroxymethyl)spiro(benzofuran-2(3H),2'-oxirane)-3,4-diol, 6-acetate
• DIDROVALTRATE (MART.)
• DIDROVALTRATE [MART.]
• BUTANOIC ACID, 3-METHYL-, (1S,2'R,4AS,6S,7AS)-6-(ACETYLOXY)-4A,5,6,7A-TETRAHYDRO-4-((3-METHYL-1-OXOBUTOXY)METHYL)SPIRO(CYCLOPENTA(C)PYRAN-7(1H),2'-OXIRAN)-1-YL ESTER
• [(1S,4aS,6S,7R,7aS)-6-acetyloxy-1-(3-methylbutanoyloxy)spiro[4a,5,6,7a-tetrahydro-1H-cyclopenta[c]pyran-7,2'-oxirane]-4-yl]methyl 3-methylbutanoate
• Isovaltrate,5-dihydro-
• SCHEMBL424675
• CHEMBL550227
• DTXCID9093854
• Butanoic acid, 3-methyl-, 6-(acetyloxy)-4a,5,6,7a-tetrahydro-4-[(3-methyl-1-oxobutoxy)methyl]spiro[cyclopenta[c]pyran-7(1H),2'-oxiran]-1-yl ester, [1S-(1.alpha.,4a.alpha.,6.alpha.,7.beta.,7a.alpha.)]-
• HY-N3741
• Isovaleric acid, 3,4-diester with 3a,4,5,6-tetrahydro-6-(hydroxymethyl)spiro[benzofuran-2(3H),2'-oxirane-3,4-diol, 6-acetate
• NSC335756
• AKOS040761620
• LMPR0102070008
• LS-46350
• XD178328
• CS-0024137
• C09776
• Q27106405
• 1,5,7a-Tetrahydro-1,6-dihydroxyspiro[cyclopenta[c]pyran-7(6H),2'-oxirane]-4-methanol 6-acetate 1,4-diisovalerate
• Butanoic acid, 3-methyl-, 6-(acetyloxy)-4a,5,6,7a-tetrahydro-4-((3-methyl-1-oxobutoxy)methyl)spiro(cyclopenta(c)pyran-7(1H),2'-oxiran)-1-yl ester, (1S-(1alpha,4aalpha,6alpha,7beta,7aalpha))-
• Butanoic acid, 6-(acetyloxy)-4a,5,6,7a-tetrahydro-4-[(3-methyl-1-oxobutoxy)methyl]spiro[cyclopenta[c]pyran-7(1H),2'-oxiran]-1-yl ester, [1S-(1.alpha.,4a.alpha.,6.alpha.,7.beta.,7a.alpha.)]-
• Isovaleric acid,4-diester with 3a,4,5,6-tetrahydro-6-(hydroxymethyl)spiro[benzofuran-2(3H),2'-oxirane-3,4-diol, 6-acetate

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9559	95.59%
Caco-2	-	0.6078	60.78%
Blood Brain Barrier	+	0.9250	92.50%
Human oral bioavailability	-	0.7571	75.71%
Subcellular localzation	Mitochondria	0.7775	77.75%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8429	84.29%
OATP1B3 inhibitior	+	0.9235	92.35%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	+	0.7822	78.22%
P-glycoprotein inhibitior	+	0.5912	59.12%
P-glycoprotein substrate	-	0.6591	65.91%
CYP3A4 substrate	+	0.6108	61.08%
CYP2C9 substrate	-	0.8053	80.53%
CYP2D6 substrate	-	0.8524	85.24%
CYP3A4 inhibition	-	0.8816	88.16%
CYP2C9 inhibition	-	0.7799	77.99%
CYP2C19 inhibition	-	0.7285	72.85%
CYP2D6 inhibition	-	0.9168	91.68%
CYP1A2 inhibition	-	0.8374	83.74%
CYP2C8 inhibition	-	0.5872	58.72%
CYP inhibitory promiscuity	-	0.8448	84.48%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.8900	89.00%
Carcinogenicity (trinary)	Non-required	0.5628	56.28%
Eye corrosion	-	0.9730	97.30%
Eye irritation	-	0.8635	86.35%
Skin irritation	-	0.7448	74.48%
Skin corrosion	-	0.9383	93.83%
Ames mutagenesis	+	0.7900	79.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4520	45.20%
Micronuclear	-	0.5900	59.00%
Hepatotoxicity	+	0.5003	50.03%
skin sensitisation	-	0.6108	61.08%
Respiratory toxicity	+	0.5111	51.11%
Reproductive toxicity	+	0.5667	56.67%
Mitochondrial toxicity	+	0.6250	62.50%
Nephrotoxicity	+	0.5590	55.90%
Acute Oral Toxicity (c)	III	0.4886	48.86%
Estrogen receptor binding	+	0.7659	76.59%
Androgen receptor binding	+	0.6106	61.06%
Thyroid receptor binding	+	0.5247	52.47%
Glucocorticoid receptor binding	+	0.7912	79.12%
Aromatase binding	+	0.5415	54.15%
PPAR gamma	+	0.5597	55.97%
Honey bee toxicity	-	0.7844	78.44%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.5400	54.00%
Fish aquatic toxicity	+	0.9523	95.23%

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	98.34%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	93.89%	91.11%
CHEMBL3137262	O60341	LSD1/CoREST complex	93.55%	97.09%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	92.85%	97.21%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	92.24%	94.45%
CHEMBL2581	P07339	Cathepsin D	89.42%	98.95%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	89.42%	85.14%
CHEMBL2996	Q05655	Protein kinase C delta	87.66%	97.79%
CHEMBL340	P08684	Cytochrome P450 3A4	85.51%	91.19%
CHEMBL1293249	Q13887	Kruppel-like factor 5	85.47%	86.33%
CHEMBL1806	P11388	DNA topoisomerase II alpha	84.94%	89.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	84.20%	99.17%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	82.44%	95.89%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	81.64%	95.56%
CHEMBL2413	P32246	C-C chemokine receptor type 1	80.41%	89.50%

Plants that contains it

• 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 vaginata

Cross-Links

• PubChem: 65689
• NPASS: NPC66504
• ChEMBL: CHEMBL550227
• LOTUS: LTS0005262
• wikiData: Q27106405