Methyl Shikimate

Details

• Internal ID: 718868c5-5eca-44fe-9bb7-bade9e555d67
• Taxonomy: Organic oxygen compounds > Organooxygen compounds > Alcohols and polyols > Cyclitols and derivatives > Shikimic acids and derivatves
• IUPAC Name: methyl (3R,4S,5R)-3,4,5-trihydroxycyclohexene-1-carboxylate
• SMILES (Canonical): COC(=O)C1=CC(C(C(C1)O)O)O
• SMILES (Isomeric): COC(=O)C1=C[C@H]([C@H]([C@@H](C1)O)O)O
• InChI: InChI=1S/C8H12O5/c1-13-8(12)4-2-5(9)7(11)6(10)3-4/h2,5-7,9-11H,3H2,1H3/t5-,6-,7-/m1/s1
• InChI Key: LSNUUAUXWJZSFD-FSDSQADBSA-N
• Popularity: 7 references in papers

Physical and Chemical Properties

• Molecular Formula: C₈H₁₂O₅
• Molecular Weight: 188.18 g/mol
• Exact Mass: 188.06847348 g/mol
• Topological Polar Surface Area (TPSA): 87.00 Ų
• XlogP: -1.40
• Atomic LogP (AlogP): -1.43
• H-Bond Acceptor: 5
• H-Bond Donor: 3
• Rotatable Bonds: 1

Synonyms

• Methyl (-)-Shikimate
• methyl (3R,4S,5R)-3,4,5-trihydroxycyclohexene-1-carboxylate
• MFCD08274584
• SCHEMBL3006812
• AKOS006286961
• (3R-(3alpha,4alpha,5beta))-3,4,5-trihydroxy-1-Cyclohexene-1-carboxylic acid methyl ester

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7725	77.25%
Caco-2	-	0.8084	80.84%
Blood Brain Barrier	-	0.6500	65.00%
Human oral bioavailability	+	0.6571	65.71%
Subcellular localzation	Mitochondria	0.7415	74.15%
OATP2B1 inhibitior	-	0.8591	85.91%
OATP1B1 inhibitior	+	0.9377	93.77%
OATP1B3 inhibitior	+	0.9572	95.72%
MATE1 inhibitior	-	0.8400	84.00%
OCT2 inhibitior	-	0.9588	95.88%
BSEP inhibitior	-	0.9563	95.63%
P-glycoprotein inhibitior	-	0.9750	97.50%
P-glycoprotein substrate	-	0.9140	91.40%
CYP3A4 substrate	-	0.5167	51.67%
CYP2C9 substrate	-	0.7943	79.43%
CYP2D6 substrate	-	0.8503	85.03%
CYP3A4 inhibition	-	0.9672	96.72%
CYP2C9 inhibition	-	0.8747	87.47%
CYP2C19 inhibition	-	0.8992	89.92%
CYP2D6 inhibition	-	0.9284	92.84%
CYP1A2 inhibition	-	0.9062	90.62%
CYP2C8 inhibition	-	0.9334	93.34%
CYP inhibitory promiscuity	-	0.9419	94.19%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.8943	89.43%
Carcinogenicity (trinary)	Non-required	0.6557	65.57%
Eye corrosion	-	0.9766	97.66%
Eye irritation	-	0.7745	77.45%
Skin irritation	-	0.6399	63.99%
Skin corrosion	-	0.9191	91.91%
Ames mutagenesis	-	0.8100	81.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6368	63.68%
Micronuclear	+	0.5200	52.00%
Hepatotoxicity	-	0.5375	53.75%
skin sensitisation	-	0.7126	71.26%
Respiratory toxicity	-	0.5444	54.44%
Reproductive toxicity	+	0.6778	67.78%
Mitochondrial toxicity	+	0.5125	51.25%
Nephrotoxicity	+	0.5902	59.02%
Acute Oral Toxicity (c)	III	0.4620	46.20%
Estrogen receptor binding	-	0.8830	88.30%
Androgen receptor binding	-	0.8453	84.53%
Thyroid receptor binding	-	0.7732	77.32%
Glucocorticoid receptor binding	-	0.7441	74.41%
Aromatase binding	-	0.8973	89.73%
PPAR gamma	-	0.8962	89.62%
Honey bee toxicity	-	0.9218	92.18%
Biodegradation	+	0.5500	55.00%
Crustacea aquatic toxicity	-	0.7900	79.00%
Fish aquatic toxicity	-	0.3646	36.46%

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	96.43%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	93.50%	91.11%
CHEMBL4040	P28482	MAP kinase ERK2	92.20%	83.82%
CHEMBL2581	P07339	Cathepsin D	88.54%	98.95%
CHEMBL4208	P20618	Proteasome component C5	80.73%	90.00%
CHEMBL2535	P11166	Glucose transporter	80.04%	98.75%

Plants that contains it

• Hydrangea macrophylla
• Sequoiadendron giganteum

Cross-Links

• PubChem: 10773951
• LOTUS: LTS0161079
• wikiData: Q105156676