Andrographolactone

Details

• Internal ID: fd7d7f57-75ee-4f21-8ba9-0a64f1dac12a
• Taxonomy: Organoheterocyclic compounds > Dihydrofurans > Furanones > Butenolides
• IUPAC Name: 4-[2-(1,3,6-trimethyl-8,9-dihydro-7H-benzo[7]annulen-2-yl)ethyl]-2H-furan-5-one
• SMILES (Canonical): CC1=CC2=C(CCC1)C(=C(C(=C2)C)CCC3=CCOC3=O)C
• SMILES (Isomeric): CC1=CC2=C(CCC1)C(=C(C(=C2)C)CCC3=CCOC3=O)C
• InChI: InChI=1S/C20H24O2/c1-13-5-4-6-19-15(3)18(14(2)12-17(19)11-13)8-7-16-9-10-22-20(16)21/h9,11-12H,4-8,10H2,1-3H3
• InChI Key: AZVREFBOZWOSCN-UHFFFAOYSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₂₄O₂
• Molecular Weight: 296.40 g/mol
• Exact Mass: 296.177630004 g/mol
• Topological Polar Surface Area (TPSA): 26.30 Ų
• XlogP: 4.70
• Atomic LogP (AlogP): 4.46
• H-Bond Acceptor: 2
• H-Bond Donor: 0
• Rotatable Bonds: 3

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	1.0000	100.00%
Caco-2	+	0.8356	83.56%
Blood Brain Barrier	+	0.7500	75.00%
Human oral bioavailability	+	0.5429	54.29%
Subcellular localzation	Mitochondria	0.5180	51.80%
OATP2B1 inhibitior	-	0.7161	71.61%
OATP1B1 inhibitior	+	0.8674	86.74%
OATP1B3 inhibitior	+	0.9438	94.38%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.7000	70.00%
BSEP inhibitior	+	0.9126	91.26%
P-glycoprotein inhibitior	-	0.6477	64.77%
P-glycoprotein substrate	-	0.7618	76.18%
CYP3A4 substrate	+	0.5134	51.34%
CYP2C9 substrate	-	0.6012	60.12%
CYP2D6 substrate	-	0.8570	85.70%
CYP3A4 inhibition	-	0.7672	76.72%
CYP2C9 inhibition	-	0.6876	68.76%
CYP2C19 inhibition	+	0.6316	63.16%
CYP2D6 inhibition	-	0.8382	83.82%
CYP1A2 inhibition	+	0.8580	85.80%
CYP2C8 inhibition	-	0.7869	78.69%
CYP inhibitory promiscuity	+	0.5000	50.00%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.8800	88.00%
Carcinogenicity (trinary)	Non-required	0.6429	64.29%
Eye corrosion	-	0.9674	96.74%
Eye irritation	-	0.7250	72.50%
Skin irritation	-	0.6817	68.17%
Skin corrosion	-	0.9631	96.31%
Ames mutagenesis	+	0.5100	51.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.3817	38.17%
Micronuclear	-	0.9000	90.00%
Hepatotoxicity	+	0.7053	70.53%
skin sensitisation	-	0.5873	58.73%
Respiratory toxicity	+	0.6111	61.11%
Reproductive toxicity	-	0.5642	56.42%
Mitochondrial toxicity	+	0.5250	52.50%
Nephrotoxicity	-	0.6968	69.68%
Acute Oral Toxicity (c)	III	0.5547	55.47%
Estrogen receptor binding	+	0.6421	64.21%
Androgen receptor binding	+	0.6626	66.26%
Thyroid receptor binding	-	0.6158	61.58%
Glucocorticoid receptor binding	+	0.7736	77.36%
Aromatase binding	-	0.5469	54.69%
PPAR gamma	+	0.7003	70.03%
Honey bee toxicity	-	0.9020	90.20%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.5900	59.00%
Fish aquatic toxicity	+	1.0000	100.00%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.17%	91.11%
CHEMBL2581	P07339	Cathepsin D	94.04%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	94.03%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	91.87%	86.33%
CHEMBL1293255	P15428	15-hydroxyprostaglandin dehydrogenase [NAD+]	90.65%	83.57%
CHEMBL3401	O75469	Pregnane X receptor	89.89%	94.73%
CHEMBL4803	P29474	Nitric-oxide synthase, endothelial	84.15%	86.00%
CHEMBL230	P35354	Cyclooxygenase-2	83.96%	89.63%
CHEMBL253	P34972	Cannabinoid CB2 receptor	82.23%	97.25%
CHEMBL4208	P20618	Proteasome component C5	81.89%	90.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	81.70%	97.09%
CHEMBL3227	P41594	Metabotropic glutamate receptor 5	80.66%	96.42%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	80.39%	93.40%
CHEMBL1806	P11388	DNA topoisomerase II alpha	80.18%	89.00%

Plants that contains it

• Andrographis paniculata

Cross-Links

• PubChem: 44206466
• NPASS: NPC40871
• LOTUS: LTS0268808
• wikiData: Q104921961