Germacra-1(10),4,11(13)-triene-12,14-dioic acid, 2-beta,6-alpha,8-alpha-trihydroxy-, 12,6:14,2-dilactone, methacrylate, (E)-

Details

• Internal ID: 79f6039a-047e-4d99-bcfc-522844fb430d
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones
• IUPAC Name: [(9E)-10-methyl-5-methylidene-6,14-dioxo-7,13-dioxatricyclo[10.2.1.04,8]pentadeca-1(15),9-dien-3-yl] 2-methylprop-2-enoate
• SMILES (Canonical): CC1=CC2C(C(CC3=CC(C1)OC3=O)OC(=O)C(=C)C)C(=C)C(=O)O2
• SMILES (Isomeric): C/C/1=C\C2C(C(CC3=CC(C1)OC3=O)OC(=O)C(=C)C)C(=C)C(=O)O2
• InChI: InChI=1S/C19H20O6/c1-9(2)17(20)24-15-8-12-7-13(23-19(12)22)5-10(3)6-14-16(15)11(4)18(21)25-14/h6-7,13-16H,1,4-5,8H2,2-3H3/b10-6+
• InChI Key: JMUOPRSXUVOHFE-UXBLZVDNSA-N
• Popularity: 38 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₉H₂₀O₆
• Molecular Weight: 344.40 g/mol
• Exact Mass: 344.12598835 g/mol
• Topological Polar Surface Area (TPSA): 78.90 Ų
• XlogP: 2.40
• Atomic LogP (AlogP): 2.16
• H-Bond Acceptor: 6
• H-Bond Donor: 0
• Rotatable Bonds: 2

Synonyms

• NSC 259726
• BRN 1662665
• Germacra-1(10),4,11(13)-triene-12,14-dioic acid, 2-beta,6-alpha,8-alpha-trihydroxy-, 12,6:14,2-dilactone, methacrylate, (E)-
• 29307-03-7
• LS-71188

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9918	99.18%
Caco-2	+	0.5509	55.09%
Blood Brain Barrier	+	0.6250	62.50%
Human oral bioavailability	-	0.5143	51.43%
Subcellular localzation	Mitochondria	0.6435	64.35%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8986	89.86%
OATP1B3 inhibitior	+	0.8773	87.73%
MATE1 inhibitior	-	0.7800	78.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	-	0.6252	62.52%
P-glycoprotein inhibitior	-	0.5156	51.56%
P-glycoprotein substrate	-	0.7876	78.76%
CYP3A4 substrate	+	0.5812	58.12%
CYP2C9 substrate	-	0.6140	61.40%
CYP2D6 substrate	-	0.8816	88.16%
CYP3A4 inhibition	-	0.7384	73.84%
CYP2C9 inhibition	-	0.8404	84.04%
CYP2C19 inhibition	-	0.7929	79.29%
CYP2D6 inhibition	-	0.9269	92.69%
CYP1A2 inhibition	-	0.6639	66.39%
CYP2C8 inhibition	-	0.7673	76.73%
CYP inhibitory promiscuity	-	0.8271	82.71%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.8743	87.43%
Carcinogenicity (trinary)	Non-required	0.5208	52.08%
Eye corrosion	-	0.9019	90.19%
Eye irritation	-	0.7404	74.04%
Skin irritation	-	0.6776	67.76%
Skin corrosion	-	0.9237	92.37%
Ames mutagenesis	-	0.6500	65.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5161	51.61%
Micronuclear	-	0.5300	53.00%
Hepatotoxicity	+	0.6018	60.18%
skin sensitisation	-	0.6203	62.03%
Respiratory toxicity	+	0.6556	65.56%
Reproductive toxicity	+	0.5889	58.89%
Mitochondrial toxicity	+	0.7750	77.50%
Nephrotoxicity	+	0.6942	69.42%
Acute Oral Toxicity (c)	III	0.4250	42.50%
Estrogen receptor binding	+	0.5778	57.78%
Androgen receptor binding	-	0.4949	49.49%
Thyroid receptor binding	+	0.5373	53.73%
Glucocorticoid receptor binding	+	0.7530	75.30%
Aromatase binding	-	0.5000	50.00%
PPAR gamma	+	0.6454	64.54%
Honey bee toxicity	-	0.6502	65.02%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.5200	52.00%
Fish aquatic toxicity	+	0.9812	98.12%

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	99.90%	83.82%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	93.82%	91.11%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	89.48%	99.23%
CHEMBL2581	P07339	Cathepsin D	88.95%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.75%	95.56%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	84.66%	94.45%
CHEMBL1293249	Q13887	Kruppel-like factor 5	84.18%	86.33%
CHEMBL3401	O75469	Pregnane X receptor	84.04%	94.73%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	81.43%	95.50%
CHEMBL5028	O14672	ADAM10	80.69%	97.50%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	80.46%	96.09%

Plants that contains it

• Andrographis paniculata

Cross-Links

• PubChem: 6381428
• NPASS: NPC146043