(E,4S,5R,6S)-2-benzyl-4,5,6,7-tetrahydroxyhept-2-enoic acid

Details

• Internal ID: 4589e722-e71b-4519-9510-4b63f5353a1b
• Taxonomy: Phenylpropanoids and polyketides > Phenylpropanoic acids
• IUPAC Name: (E,4S,5R,6S)-2-benzyl-4,5,6,7-tetrahydroxyhept-2-enoic acid
• SMILES (Canonical): C1=CC=C(C=C1)CC(=CC(C(C(CO)O)O)O)C(=O)O
• SMILES (Isomeric): C1=CC=C(C=C1)C/C(=C\[C@@H]([C@H]([C@H](CO)O)O)O)/C(=O)O
• InChI: InChI=1S/C14H18O6/c15-8-12(17)13(18)11(16)7-10(14(19)20)6-9-4-2-1-3-5-9/h1-5,7,11-13,15-18H,6,8H2,(H,19,20)/b10-7+/t11-,12-,13+/m0/s1
• InChI Key: ZYSLTUAGDIMLQK-PUJUQVOMSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₄H₁₈O₆
• Molecular Weight: 282.29 g/mol
• Exact Mass: 282.11033829 g/mol
• Topological Polar Surface Area (TPSA): 118.00 Ų
• XlogP: -0.60
• Atomic LogP (AlogP): -0.68
• H-Bond Acceptor: 5
• H-Bond Donor: 5
• Rotatable Bonds: 7

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7480	74.80%
Caco-2	-	0.9380	93.80%
Blood Brain Barrier	-	0.5000	50.00%
Human oral bioavailability	-	0.6714	67.14%
Subcellular localzation	Mitochondria	0.7612	76.12%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9296	92.96%
OATP1B3 inhibitior	+	0.9396	93.96%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.9088	90.88%
BSEP inhibitior	-	0.9155	91.55%
P-glycoprotein inhibitior	-	0.9747	97.47%
P-glycoprotein substrate	-	0.9396	93.96%
CYP3A4 substrate	-	0.6167	61.67%
CYP2C9 substrate	-	0.7723	77.23%
CYP2D6 substrate	-	0.8711	87.11%
CYP3A4 inhibition	-	0.9232	92.32%
CYP2C9 inhibition	-	0.8428	84.28%
CYP2C19 inhibition	-	0.9182	91.82%
CYP2D6 inhibition	-	0.8984	89.84%
CYP1A2 inhibition	-	0.8400	84.00%
CYP2C8 inhibition	-	0.8344	83.44%
CYP inhibitory promiscuity	-	0.9049	90.49%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.8900	89.00%
Carcinogenicity (trinary)	Non-required	0.7827	78.27%
Eye corrosion	-	0.9940	99.40%
Eye irritation	-	0.6468	64.68%
Skin irritation	-	0.6710	67.10%
Skin corrosion	-	0.9585	95.85%
Ames mutagenesis	-	0.7337	73.37%
Human Ether-a-go-go-Related Gene inhibition	-	0.6956	69.56%
Micronuclear	-	0.7482	74.82%
Hepatotoxicity	-	0.7500	75.00%
skin sensitisation	-	0.6389	63.89%
Respiratory toxicity	+	0.6000	60.00%
Reproductive toxicity	-	0.5778	57.78%
Mitochondrial toxicity	-	0.6625	66.25%
Nephrotoxicity	-	0.7204	72.04%
Acute Oral Toxicity (c)	III	0.4777	47.77%
Estrogen receptor binding	-	0.6335	63.35%
Androgen receptor binding	-	0.5844	58.44%
Thyroid receptor binding	-	0.5787	57.87%
Glucocorticoid receptor binding	-	0.5000	50.00%
Aromatase binding	-	0.4872	48.72%
PPAR gamma	+	0.6392	63.92%
Honey bee toxicity	-	0.9618	96.18%
Biodegradation	-	0.6000	60.00%
Crustacea aquatic toxicity	-	0.7800	78.00%
Fish aquatic toxicity	+	0.7031	70.31%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	96.24%	98.95%
CHEMBL221	P23219	Cyclooxygenase-1	93.45%	90.17%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	90.16%	95.50%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.24%	95.56%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	89.10%	94.62%
CHEMBL3060	Q9Y345	Glycine transporter 2	88.66%	99.17%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	88.47%	96.09%
CHEMBL3401	O75469	Pregnane X receptor	82.29%	94.73%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	80.19%	91.11%

Plants that contains it

• Drypetes gossweileri

Cross-Links

• PubChem: 163187198
• LOTUS: LTS0273340
• wikiData: Q105386382