Methyl eichlerianate

Details

• Internal ID: 6269691e-d396-494c-b750-5b8554cf19a4
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Diterpene glycosides
• IUPAC Name: methyl 3-[(3S,3aR,5aR,6S,7S,9aR,9bR)-3-[(2S,5S)-5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-6,9a,9b-trimethyl-7-prop-1-en-2-yl-1,2,3,3a,4,5,5a,7,8,9-decahydrocyclopenta[a]naphthalen-6-yl]propanoate
• SMILES (Canonical): CC(=C)C1CCC2(C(C1(C)CCC(=O)OC)CCC3C2(CCC3C4(CCC(O4)C(C)(C)O)C)C)C
• SMILES (Isomeric): CC(=C)[C@@H]1CC[C@@]2([C@@H]([C@@]1(C)CCC(=O)OC)CC[C@H]3[C@]2(CC[C@@H]3[C@@]4(CC[C@H](O4)C(C)(C)O)C)C)C
• InChI: InChI=1S/C31H52O4/c1-20(2)21-12-18-30(7)24(28(21,5)16-15-26(32)34-9)11-10-22-23(13-17-29(22,30)6)31(8)19-14-25(35-31)27(3,4)33/h21-25,33H,1,10-19H2,2-9H3/t21-,22+,23-,24+,25-,28-,29+,30+,31-/m0/s1
• InChI Key: TWFMQZXDUHCZFN-GVEJJQTFSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₃₁H₅₂O₄
• Molecular Weight: 488.70 g/mol
• Exact Mass: 488.38656014 g/mol
• Topological Polar Surface Area (TPSA): 55.80 Ų
• XlogP: 7.60
• Atomic LogP (AlogP): 7.09
• H-Bond Acceptor: 4
• H-Bond Donor: 1
• Rotatable Bonds: 6

Synonyms

• Methyl shorate
• 56421-12-6
• CHEMBL3109456
• 3,4-Secodammar-4(28)-en-3-oic acid, 20,24-epoxy-25-hydroxy-, methyl ester, (24S)-; Eichlerianic acid methyl ester
• AKOS032962445
• 21671-01-2
• methyl 3-[(3S,3aR,5aR,6S,7S,9aR,9bR)-3-[(2S,5S)-5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-6,9a,9b-trimethyl-7-prop-1-en-2-yl-1,2,3,3a,4,5,5a,7,8,9-decahydrocyclopenta[a]naphthalen-6-yl]propanoate

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9871	98.71%
Caco-2	-	0.6238	62.38%
Blood Brain Barrier	+	0.7750	77.50%
Human oral bioavailability	-	0.6571	65.71%
Subcellular localzation	Mitochondria	0.6642	66.42%
OATP2B1 inhibitior	-	0.5680	56.80%
OATP1B1 inhibitior	+	0.8746	87.46%
OATP1B3 inhibitior	-	0.4183	41.83%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.7250	72.50%
BSEP inhibitior	+	0.8126	81.26%
P-glycoprotein inhibitior	+	0.5768	57.68%
P-glycoprotein substrate	+	0.5309	53.09%
CYP3A4 substrate	+	0.7376	73.76%
CYP2C9 substrate	-	0.7980	79.80%
CYP2D6 substrate	-	0.8696	86.96%
CYP3A4 inhibition	+	0.6372	63.72%
CYP2C9 inhibition	-	0.5317	53.17%
CYP2C19 inhibition	-	0.5998	59.98%
CYP2D6 inhibition	-	0.9240	92.40%
CYP1A2 inhibition	-	0.7035	70.35%
CYP2C8 inhibition	+	0.6303	63.03%
CYP inhibitory promiscuity	-	0.5526	55.26%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.8900	89.00%
Carcinogenicity (trinary)	Non-required	0.6510	65.10%
Eye corrosion	-	0.9877	98.77%
Eye irritation	-	0.9189	91.89%
Skin irritation	-	0.6510	65.10%
Skin corrosion	-	0.9497	94.97%
Ames mutagenesis	-	0.6600	66.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6616	66.16%
Micronuclear	-	0.7500	75.00%
Hepatotoxicity	-	0.7125	71.25%
skin sensitisation	-	0.7495	74.95%
Respiratory toxicity	+	0.6111	61.11%
Reproductive toxicity	+	0.6333	63.33%
Mitochondrial toxicity	+	0.6875	68.75%
Nephrotoxicity	-	0.6586	65.86%
Acute Oral Toxicity (c)	III	0.4944	49.44%
Estrogen receptor binding	+	0.6749	67.49%
Androgen receptor binding	+	0.7451	74.51%
Thyroid receptor binding	+	0.5727	57.27%
Glucocorticoid receptor binding	+	0.7588	75.88%
Aromatase binding	+	0.6820	68.20%
PPAR gamma	+	0.5903	59.03%
Honey bee toxicity	-	0.6899	68.99%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.5400	54.00%
Fish aquatic toxicity	+	0.9968	99.68%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4040	P28482	MAP kinase ERK2	98.99%	83.82%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.96%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	96.19%	94.45%
CHEMBL253	P34972	Cannabinoid CB2 receptor	95.73%	97.25%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.17%	96.09%
CHEMBL218	P21554	Cannabinoid CB1 receptor	93.98%	96.61%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	93.43%	96.95%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	88.46%	95.50%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	87.76%	92.62%
CHEMBL4227	P25090	Lipoxin A4 receptor	87.30%	100.00%
CHEMBL4681	P42330	Aldo-keto-reductase family 1 member C3	86.69%	89.05%
CHEMBL3713062	P10646	Tissue factor pathway inhibitor	85.65%	97.33%
CHEMBL4051	P13569	Cystic fibrosis transmembrane conductance regulator	85.41%	95.71%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	84.51%	96.77%
CHEMBL5028	O14672	ADAM10	83.64%	97.50%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	83.00%	91.07%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	82.68%	96.90%
CHEMBL340	P08684	Cytochrome P450 3A4	82.47%	91.19%
CHEMBL1293249	Q13887	Kruppel-like factor 5	82.30%	86.33%
CHEMBL233	P35372	Mu opioid receptor	82.28%	97.93%
CHEMBL3430907	Q96GD4	Aurora kinase B/Inner centromere protein	82.02%	97.50%
CHEMBL5888	Q99558	Mitogen-activated protein kinase kinase kinase 14	81.88%	100.00%
CHEMBL1871	P10275	Androgen Receptor	81.69%	96.43%
CHEMBL1907601	P11802	Cyclin-dependent kinase 4/cyclin D1	81.43%	98.99%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	81.05%	97.14%
CHEMBL2095194	P08709	Coagulation factor VII/tissue factor	80.64%	99.17%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	80.41%	85.14%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	80.33%	94.33%

Plants that contains it

• Cinnamomum aromaticum

Cross-Links

• PubChem: 76313960
• NPASS: NPC48824