(2S,3S,5E)-5-ethylidene-2-hydroxy-2-(hydroxymethyl)-3-methylhexanedioic acid

Details

• Internal ID: d164b4ea-6227-404c-90bc-a6485933a6f2
• Taxonomy: Organic acids and derivatives > Hydroxy acids and derivatives > Medium-chain hydroxy acids and derivatives
• IUPAC Name: (2S,3S,5E)-5-ethylidene-2-hydroxy-2-(hydroxymethyl)-3-methylhexanedioic acid
• SMILES (Canonical): CC=C(CC(C)C(CO)(C(=O)O)O)C(=O)O
• SMILES (Isomeric): C/C=C(\C[C@H](C)[C@](CO)(C(=O)O)O)/C(=O)O
• InChI: InChI=1S/C10H16O6/c1-3-7(8(12)13)4-6(2)10(16,5-11)9(14)15/h3,6,11,16H,4-5H2,1-2H3,(H,12,13)(H,14,15)/b7-3+/t6-,10+/m0/s1
• InChI Key: WGBRYLLSVMNVMD-RBJXLHOQSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₀H₁₆O₆
• Molecular Weight: 232.23 g/mol
• Exact Mass: 232.09468823 g/mol
• Topological Polar Surface Area (TPSA): 115.00 Ų
• XlogP: -0.20
• Atomic LogP (AlogP): -0.15
• H-Bond Acceptor: 4
• 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	+	0.7317	73.17%
Caco-2	-	0.7935	79.35%
Blood Brain Barrier	+	0.5432	54.32%
Human oral bioavailability	-	0.5571	55.71%
Subcellular localzation	Mitochondria	0.7708	77.08%
OATP2B1 inhibitior	-	0.8504	85.04%
OATP1B1 inhibitior	+	0.8806	88.06%
OATP1B3 inhibitior	+	0.9332	93.32%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.8588	85.88%
BSEP inhibitior	-	0.9540	95.40%
P-glycoprotein inhibitior	-	0.9919	99.19%
P-glycoprotein substrate	-	0.9422	94.22%
CYP3A4 substrate	-	0.6246	62.46%
CYP2C9 substrate	-	0.5818	58.18%
CYP2D6 substrate	-	0.9079	90.79%
CYP3A4 inhibition	-	0.8900	89.00%
CYP2C9 inhibition	-	0.7948	79.48%
CYP2C19 inhibition	-	0.8515	85.15%
CYP2D6 inhibition	-	0.8893	88.93%
CYP1A2 inhibition	-	0.8305	83.05%
CYP2C8 inhibition	-	0.9816	98.16%
CYP inhibitory promiscuity	-	0.9532	95.32%
UGT catelyzed	+	0.5362	53.62%
Carcinogenicity (binary)	-	0.8311	83.11%
Carcinogenicity (trinary)	Non-required	0.7327	73.27%
Eye corrosion	-	0.9771	97.71%
Eye irritation	-	0.6960	69.60%
Skin irritation	-	0.7324	73.24%
Skin corrosion	-	0.9691	96.91%
Ames mutagenesis	-	0.5828	58.28%
Human Ether-a-go-go-Related Gene inhibition	-	0.8356	83.56%
Micronuclear	-	0.8100	81.00%
Hepatotoxicity	-	0.6125	61.25%
skin sensitisation	-	0.8192	81.92%
Respiratory toxicity	-	0.7556	75.56%
Reproductive toxicity	-	0.8386	83.86%
Mitochondrial toxicity	-	0.7875	78.75%
Nephrotoxicity	-	0.6076	60.76%
Acute Oral Toxicity (c)	IV	0.4601	46.01%
Estrogen receptor binding	-	0.8947	89.47%
Androgen receptor binding	-	0.7921	79.21%
Thyroid receptor binding	-	0.6493	64.93%
Glucocorticoid receptor binding	-	0.7388	73.88%
Aromatase binding	-	0.7640	76.40%
PPAR gamma	-	0.8173	81.73%
Honey bee toxicity	-	0.9689	96.89%
Biodegradation	-	0.6250	62.50%
Crustacea aquatic toxicity	-	0.8000	80.00%
Fish aquatic toxicity	+	0.8745	87.45%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	88.36%	98.95%
CHEMBL1907591	P30926	Neuronal acetylcholine receptor; alpha4/beta4	87.65%	100.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	85.60%	96.09%
CHEMBL3892	Q99500	Sphingosine 1-phosphate receptor Edg-3	84.00%	97.29%
CHEMBL3060	Q9Y345	Glycine transporter 2	83.95%	99.17%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	80.40%	89.34%

Plants that contains it

• Senecio isatideus
• Xenophyllum decorum

Cross-Links

• PubChem: 163071722
• LOTUS: LTS0156957
• wikiData: Q105304326