[(1R,2R,4aR,5R,8aS)-1,4a-dimethyl-6-methylidene-5-[(E)-2-[(5E)-5-[(2E,7E)-2-methylnona-2,7-dienylidene]-2-oxofuran-3-yl]ethenyl]-2-(pyridine-3-carbonyloxy)-3,4,5,7,8,8a-hexahydro-2H-naphthalen-1-yl]methyl pyridine-3-carboxylate

Details

• Internal ID: 3d048a3f-1760-4ad5-9ad2-c96eecb98dc6
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Diterpene lactones
• IUPAC Name: [(1R,2R,4aR,5R,8aS)-1,4a-dimethyl-6-methylidene-5-[(E)-2-[(5E)-5-[(2E,7E)-2-methylnona-2,7-dienylidene]-2-oxofuran-3-yl]ethenyl]-2-(pyridine-3-carbonyloxy)-3,4,5,7,8,8a-hexahydro-2H-naphthalen-1-yl]methyl pyridine-3-carboxylate
• SMILES (Canonical): CC=CCCCC=C(C)C=C1C=C(C(=O)O1)C=CC2C(=C)CCC3C2(CCC(C3(C)COC(=O)C4=CN=CC=C4)OC(=O)C5=CN=CC=C5)C
• SMILES (Isomeric): C/C=C/CCC/C=C(\C)/C=C/1\C=C(C(=O)O1)/C=C/[C@@H]2C(=C)CC[C@H]3[C@]2(CC[C@H]([C@@]3(C)COC(=O)C4=CN=CC=C4)OC(=O)C5=CN=CC=C5)C
• InChI: InChI=1S/C42H48N2O6/c1-6-7-8-9-10-13-29(2)24-34-25-31(39(46)49-34)17-18-35-30(3)16-19-36-41(35,4)21-20-37(50-40(47)33-15-12-23-44-27-33)42(36,5)28-48-38(45)32-14-11-22-43-26-32/h6-7,11-15,17-18,22-27,35-37H,3,8-10,16,19-21,28H2,1-2,4-5H3/b7-6+,18-17+,29-13+,34-24+/t35-,36+,37-,41+,42+/m1/s1
• InChI Key: FGJYTYSOHPJTRK-SSGBKKNDSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₄₂H₄₈N₂O₆
• Molecular Weight: 676.80 g/mol
• Exact Mass: 676.35123726 g/mol
• Topological Polar Surface Area (TPSA): 105.00 Ų
• XlogP: 8.90
• Atomic LogP (AlogP): 8.86
• H-Bond Acceptor: 8
• H-Bond Donor: 0
• Rotatable Bonds: 12

Synonyms

• BDBM50210447
• 14-deoxy-11,12-didehydro-3,19-dinicotinate-15-(2,8-dimethanyl-2,7-octanedieneylidene)-andrographolide

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9789	97.89%
Caco-2	-	0.8264	82.64%
Blood Brain Barrier	+	0.7500	75.00%
Human oral bioavailability	-	0.6143	61.43%
Subcellular localzation	Mitochondria	0.7921	79.21%
OATP2B1 inhibitior	+	0.8573	85.73%
OATP1B1 inhibitior	+	0.7863	78.63%
OATP1B3 inhibitior	+	0.8535	85.35%
MATE1 inhibitior	-	0.8600	86.00%
OCT2 inhibitior	-	0.6000	60.00%
BSEP inhibitior	+	0.9950	99.50%
P-glycoprotein inhibitior	+	0.8561	85.61%
P-glycoprotein substrate	+	0.6474	64.74%
CYP3A4 substrate	+	0.7326	73.26%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8711	87.11%
CYP3A4 inhibition	+	0.7607	76.07%
CYP2C9 inhibition	-	0.7722	77.22%
CYP2C19 inhibition	-	0.7171	71.71%
CYP2D6 inhibition	-	0.9071	90.71%
CYP1A2 inhibition	+	0.5212	52.12%
CYP2C8 inhibition	+	0.8804	88.04%
CYP inhibitory promiscuity	+	0.5627	56.27%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.5877	58.77%
Eye corrosion	-	0.9882	98.82%
Eye irritation	-	0.9146	91.46%
Skin irritation	-	0.7253	72.53%
Skin corrosion	-	0.9359	93.59%
Ames mutagenesis	-	0.6654	66.54%
Human Ether-a-go-go-Related Gene inhibition	+	0.8646	86.46%
Micronuclear	-	0.5300	53.00%
Hepatotoxicity	-	0.5851	58.51%
skin sensitisation	-	0.8403	84.03%
Respiratory toxicity	+	0.7556	75.56%
Reproductive toxicity	+	0.8333	83.33%
Mitochondrial toxicity	+	0.7500	75.00%
Nephrotoxicity	-	0.8120	81.20%
Acute Oral Toxicity (c)	III	0.5530	55.30%
Estrogen receptor binding	+	0.8291	82.91%
Androgen receptor binding	+	0.7036	70.36%
Thyroid receptor binding	+	0.6554	65.54%
Glucocorticoid receptor binding	+	0.7901	79.01%
Aromatase binding	+	0.5544	55.44%
PPAR gamma	+	0.6817	68.17%
Honey bee toxicity	-	0.7251	72.51%
Biodegradation	-	0.9250	92.50%
Crustacea aquatic toxicity	+	0.5300	53.00%
Fish aquatic toxicity	+	0.9959	99.59%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL2074	O43451	Maltase-glucoamylase	28000 nM	IC50	PMID: 17428667

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.07%	91.11%
CHEMBL1293249	Q13887	Kruppel-like factor 5	96.15%	86.33%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	94.21%	99.23%
CHEMBL2996	Q05655	Protein kinase C delta	92.42%	97.79%
CHEMBL2581	P07339	Cathepsin D	91.32%	98.95%
CHEMBL4224	P49759	Dual specificty protein kinase CLK1	90.41%	85.30%
CHEMBL3060	Q9Y345	Glycine transporter 2	89.35%	99.17%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	89.23%	94.45%
CHEMBL1994	P08235	Mineralocorticoid receptor	88.38%	100.00%
CHEMBL1829	O15379	Histone deacetylase 3	88.24%	95.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	88.21%	95.89%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	87.72%	89.34%
CHEMBL2535	P11166	Glucose transporter	87.03%	98.75%
CHEMBL5028	O14672	ADAM10	86.59%	97.50%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	85.65%	96.09%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	85.59%	82.69%
CHEMBL3145	P42338	PI3-kinase p110-beta subunit	83.23%	98.75%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	83.19%	91.07%
CHEMBL1806	P11388	DNA topoisomerase II alpha	82.85%	89.00%
CHEMBL4227	P25090	Lipoxin A4 receptor	81.72%	100.00%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	81.16%	94.33%

Plants that contains it

• Andrographis paniculata

Cross-Links

• PubChem: 44437487
• NPASS: NPC289086
• ChEMBL: CHEMBL396677