Eichlerianic acid

Details

• Internal ID: d6ce4b4a-6535-45b0-8a1d-4cb08a6f9ed2
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Diterpene glycosides
• IUPAC Name: 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]propanoic acid
• SMILES (Canonical): CC(=C)C1CCC2(C(C1(C)CCC(=O)O)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)O)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/C30H50O4/c1-19(2)20-11-17-29(7)23(27(20,5)15-14-25(31)32)10-9-21-22(12-16-28(21,29)6)30(8)18-13-24(34-30)26(3,4)33/h20-24,33H,1,9-18H2,2-8H3,(H,31,32)/t20-,21+,22-,23+,24-,27-,28+,29+,30-/m0/s1
• InChI Key: ZKBGKWZSOPPDSD-ZFQFSHTNSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₀H₅₀O₄
• Molecular Weight: 474.70 g/mol
• Exact Mass: 474.37091007 g/mol
• Topological Polar Surface Area (TPSA): 66.80 Ų
• XlogP: 7.30
• Atomic LogP (AlogP): 7.00
• H-Bond Acceptor: 3
• H-Bond Donor: 2
• Rotatable Bonds: 6

Synonyms

• 56421-13-7
• CHEBI:70463
• CHEMBL479140
• DTXSID501098817
• HY-N3801
• AKOS032962140
• CS-0024247
• Q27138800
• (3S,3aR,5aR,6S,7S,9aR,9bR)-Dodecahydro-6,9a,9b-trimethyl-7-(1-methylethenyl)-3-[(2S,5S)-tetrahydro-5-(1-hydroxy-1-methylethyl)-2-methyl-2-furanyl]-1H-benz[e]indene-6-propanoic acid
• 1H-Benz[e]indene-6-propanoic acid, dodecahydro-6,9a,9b-trimethyl-7-(1-methylethenyl)-3-[tetrahydro-5-(1-hydroxy-1-methylethyl)-2-methyl-2-furanyl]-, [3S-[3(2R*,5R*),3a,5a,6,7,9a,9b]]-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9891	98.91%
Caco-2	-	0.6183	61.83%
Blood Brain Barrier	+	0.5250	52.50%
Human oral bioavailability	-	0.5857	58.57%
Subcellular localzation	Mitochondria	0.6883	68.83%
OATP2B1 inhibitior	-	0.5665	56.65%
OATP1B1 inhibitior	+	0.8775	87.75%
OATP1B3 inhibitior	+	0.8193	81.93%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	+	0.7401	74.01%
P-glycoprotein inhibitior	-	0.5162	51.62%
P-glycoprotein substrate	-	0.5683	56.83%
CYP3A4 substrate	+	0.7146	71.46%
CYP2C9 substrate	-	0.7948	79.48%
CYP2D6 substrate	-	0.8727	87.27%
CYP3A4 inhibition	+	0.5569	55.69%
CYP2C9 inhibition	-	0.7751	77.51%
CYP2C19 inhibition	-	0.7419	74.19%
CYP2D6 inhibition	-	0.9306	93.06%
CYP1A2 inhibition	-	0.8137	81.37%
CYP2C8 inhibition	+	0.5517	55.17%
CYP inhibitory promiscuity	-	0.6973	69.73%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.8900	89.00%
Carcinogenicity (trinary)	Non-required	0.6314	63.14%
Eye corrosion	-	0.9896	98.96%
Eye irritation	-	0.9297	92.97%
Skin irritation	-	0.5281	52.81%
Skin corrosion	-	0.9403	94.03%
Ames mutagenesis	-	0.7100	71.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.3605	36.05%
Micronuclear	-	0.8100	81.00%
Hepatotoxicity	-	0.5500	55.00%
skin sensitisation	-	0.7019	70.19%
Respiratory toxicity	+	0.6889	68.89%
Reproductive toxicity	+	0.6889	68.89%
Mitochondrial toxicity	+	0.8000	80.00%
Nephrotoxicity	-	0.8172	81.72%
Acute Oral Toxicity (c)	III	0.4721	47.21%
Estrogen receptor binding	+	0.6786	67.86%
Androgen receptor binding	+	0.7389	73.89%
Thyroid receptor binding	+	0.5937	59.37%
Glucocorticoid receptor binding	+	0.8066	80.66%
Aromatase binding	+	0.7024	70.24%
PPAR gamma	+	0.5886	58.86%
Honey bee toxicity	-	0.7845	78.45%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.6874	68.74%
Fish aquatic toxicity	+	0.9974	99.74%

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	99.08%	83.82%
CHEMBL253	P34972	Cannabinoid CB2 receptor	95.96%	97.25%
CHEMBL218	P21554	Cannabinoid CB1 receptor	95.84%	96.61%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.42%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	92.59%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	91.45%	94.45%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	89.96%	96.95%
CHEMBL4681	P42330	Aldo-keto-reductase family 1 member C3	89.56%	89.05%
CHEMBL2581	P07339	Cathepsin D	88.37%	98.95%
CHEMBL5285	Q99683	Mitogen-activated protein kinase kinase kinase 5	86.95%	92.26%
CHEMBL4618	P09960	Leukotriene A4 hydrolase	84.49%	97.86%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	84.37%	95.50%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	84.18%	93.04%
CHEMBL1293249	Q13887	Kruppel-like factor 5	84.14%	86.33%
CHEMBL4227	P25090	Lipoxin A4 receptor	83.94%	100.00%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	82.85%	93.00%
CHEMBL5028	O14672	ADAM10	81.94%	97.50%
CHEMBL3713062	P10646	Tissue factor pathway inhibitor	81.23%	97.33%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	81.18%	96.77%
CHEMBL1994	P08235	Mineralocorticoid receptor	81.10%	100.00%
CHEMBL1163125	O60885	Bromodomain-containing protein 4	81.02%	97.31%
CHEMBL1806	P11388	DNA topoisomerase II alpha	80.94%	89.00%
CHEMBL340	P08684	Cytochrome P450 3A4	80.66%	91.19%

Plants that contains it

• Aglaia elaeagnoidea
• Aglaia elliptica
• Aglaia foveolata
• Aglaia lawii
• Aglaia leucophylla
• Aglaia perviridis
• Aglaia rubiginosa
• Cabralea canjerana
• Cinnamomum aromaticum
• Dysoxylum mollissimum subsp. molle
• Purshia mexicana

Cross-Links

• PubChem: 12315516
• NPASS: NPC229407
• LOTUS: LTS0166416
• wikiData: Q27138800