(2E)-6-[(6S)-3a,5-dihydroxy-6-(hydroxymethyl)-4-oxo-3,5,6,7a-tetrahydro-2H-furo[2,3-b]pyran-3-yl]-2-methylhepta-2,6-dienoic acid

Details

• Internal ID: dec2fd84-573d-42d9-8fbb-b542ab7454c6
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Monoterpenoids > Bicyclic monoterpenoids
• IUPAC Name: (2E)-6-[(6S)-3a,5-dihydroxy-6-(hydroxymethyl)-4-oxo-3,5,6,7a-tetrahydro-2H-furo[2,3-b]pyran-3-yl]-2-methylhepta-2,6-dienoic acid
• SMILES (Canonical): CC(=CCCC(=C)C1COC2C1(C(=O)C(C(O2)CO)O)O)C(=O)O
• SMILES (Isomeric): C/C(=C\CCC(=C)C1COC2C1(C(=O)C([C@@H](O2)CO)O)O)/C(=O)O
• InChI: InChI=1S/C16H22O8/c1-8(4-3-5-9(2)14(20)21)10-7-23-15-16(10,22)13(19)12(18)11(6-17)24-15/h5,10-12,15,17-18,22H,1,3-4,6-7H2,2H3,(H,20,21)/b9-5+/t10?,11-,12?,15?,16?/m0/s1
• InChI Key: DLYSHNRKPFPELT-KPZGIQGDSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₆H₂₂O₈
• Molecular Weight: 342.34 g/mol
• Exact Mass: 342.13146766 g/mol
• Topological Polar Surface Area (TPSA): 134.00 Ų
• XlogP: 0.00
• Atomic LogP (AlogP): -0.62
• H-Bond Acceptor: 7
• H-Bond Donor: 4
• Rotatable Bonds: 6

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7632	76.32%
Caco-2	-	0.7402	74.02%
Blood Brain Barrier	+	0.5527	55.27%
Human oral bioavailability	-	0.6286	62.86%
Subcellular localzation	Mitochondria	0.8310	83.10%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8393	83.93%
OATP1B3 inhibitior	+	0.9510	95.10%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.6092	60.92%
BSEP inhibitior	-	0.7520	75.20%
P-glycoprotein inhibitior	-	0.8649	86.49%
P-glycoprotein substrate	-	0.7707	77.07%
CYP3A4 substrate	+	0.5934	59.34%
CYP2C9 substrate	-	0.8042	80.42%
CYP2D6 substrate	-	0.9045	90.45%
CYP3A4 inhibition	-	0.9684	96.84%
CYP2C9 inhibition	-	0.9208	92.08%
CYP2C19 inhibition	-	0.9195	91.95%
CYP2D6 inhibition	-	0.9431	94.31%
CYP1A2 inhibition	-	0.8801	88.01%
CYP2C8 inhibition	-	0.8114	81.14%
CYP inhibitory promiscuity	-	0.9518	95.18%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.5724	57.24%
Eye corrosion	-	0.9852	98.52%
Eye irritation	-	0.9639	96.39%
Skin irritation	-	0.6103	61.03%
Skin corrosion	-	0.9213	92.13%
Ames mutagenesis	+	0.5900	59.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7877	78.77%
Micronuclear	-	0.8600	86.00%
Hepatotoxicity	+	0.5500	55.00%
skin sensitisation	-	0.8851	88.51%
Respiratory toxicity	+	0.5222	52.22%
Reproductive toxicity	+	0.6667	66.67%
Mitochondrial toxicity	+	0.7000	70.00%
Nephrotoxicity	-	0.6427	64.27%
Acute Oral Toxicity (c)	III	0.5372	53.72%
Estrogen receptor binding	+	0.7074	70.74%
Androgen receptor binding	+	0.6443	64.43%
Thyroid receptor binding	+	0.5983	59.83%
Glucocorticoid receptor binding	+	0.6878	68.78%
Aromatase binding	+	0.6584	65.84%
PPAR gamma	-	0.5499	54.99%
Honey bee toxicity	-	0.8362	83.62%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	-	0.5900	59.00%
Fish aquatic toxicity	+	0.9153	91.53%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.59%	91.11%
CHEMBL4040	P28482	MAP kinase ERK2	96.74%	83.82%
CHEMBL340	P08684	Cytochrome P450 3A4	90.64%	91.19%
CHEMBL2581	P07339	Cathepsin D	90.03%	98.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	89.52%	89.00%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	86.99%	93.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	83.80%	95.56%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	83.66%	99.23%
CHEMBL1994	P08235	Mineralocorticoid receptor	81.55%	100.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	81.17%	94.45%

Plants that contains it

• Lycopodiella cernua

Cross-Links

• PubChem: 5321272
• NPASS: NPC235060