Madindoline A/B

Details

• Internal ID: 9471c94d-ff4b-4066-841e-0c7900532900
• Taxonomy: Organoheterocyclic compounds > Indoles and derivatives
• IUPAC Name: 2-[(8b-hydroxy-2,3a-dihydro-1H-furo[2,3-b]indol-4-yl)methyl]-4-butyl-2,5-dimethylcyclopentane-1,3-dione
• SMILES (Canonical): CCCCC1C(C(=O)C(C1=O)(C)CN2C3C(CCO3)(C4=CC=CC=C42)O)C
• SMILES (Isomeric): CCCCC1C(C(=O)C(C1=O)(C)CN2C3C(CCO3)(C4=CC=CC=C42)O)C
• InChI: InChI=1S/C22H29NO4/c1-4-5-8-15-14(2)18(24)21(3,19(15)25)13-23-17-10-7-6-9-16(17)22(26)11-12-27-20(22)23/h6-7,9-10,14-15,20,26H,4-5,8,11-13H2,1-3H3
• InChI Key: YJLIDBBCWAQBOC-UHFFFAOYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₂H₂₉NO₄
• Molecular Weight: 371.50 g/mol
• Exact Mass: 371.20965841 g/mol
• Topological Polar Surface Area (TPSA): 66.80 Ų
• XlogP: 3.30
• Atomic LogP (AlogP): 3.04
• H-Bond Acceptor: 5
• H-Bond Donor: 1
• Rotatable Bonds: 5

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9390	93.90%
Caco-2	+	0.6555	65.55%
Blood Brain Barrier	+	0.6250	62.50%
Human oral bioavailability	-	0.6143	61.43%
Subcellular localzation	Mitochondria	0.5306	53.06%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8441	84.41%
OATP1B3 inhibitior	+	0.9290	92.90%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	+	0.9305	93.05%
P-glycoprotein inhibitior	-	0.4316	43.16%
P-glycoprotein substrate	-	0.5076	50.76%
CYP3A4 substrate	+	0.6523	65.23%
CYP2C9 substrate	-	0.6187	61.87%
CYP2D6 substrate	-	0.7783	77.83%
CYP3A4 inhibition	+	0.5919	59.19%
CYP2C9 inhibition	-	0.6547	65.47%
CYP2C19 inhibition	-	0.6151	61.51%
CYP2D6 inhibition	-	0.9251	92.51%
CYP1A2 inhibition	-	0.8851	88.51%
CYP2C8 inhibition	-	0.5862	58.62%
CYP inhibitory promiscuity	-	0.8235	82.35%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.8600	86.00%
Carcinogenicity (trinary)	Non-required	0.5432	54.32%
Eye corrosion	-	0.9893	98.93%
Eye irritation	-	0.9862	98.62%
Skin irritation	-	0.7908	79.08%
Skin corrosion	-	0.9236	92.36%
Ames mutagenesis	-	0.5200	52.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4111	41.11%
Micronuclear	+	0.6700	67.00%
Hepatotoxicity	+	0.5042	50.42%
skin sensitisation	-	0.8718	87.18%
Respiratory toxicity	+	0.8333	83.33%
Reproductive toxicity	+	0.8556	85.56%
Mitochondrial toxicity	+	0.8500	85.00%
Nephrotoxicity	+	0.4513	45.13%
Acute Oral Toxicity (c)	III	0.6627	66.27%
Estrogen receptor binding	+	0.8002	80.02%
Androgen receptor binding	+	0.6930	69.30%
Thyroid receptor binding	+	0.5509	55.09%
Glucocorticoid receptor binding	+	0.6682	66.82%
Aromatase binding	+	0.6384	63.84%
PPAR gamma	+	0.6158	61.58%
Honey bee toxicity	-	0.9468	94.68%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	+	0.5600	56.00%
Fish aquatic toxicity	+	0.7862	78.62%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL240	Q12809	HERG	99.46%	89.76%
CHEMBL2581	P07339	Cathepsin D	97.64%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.73%	96.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	95.87%	86.33%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.32%	91.11%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	94.03%	82.69%
CHEMBL230	P35354	Cyclooxygenase-2	92.68%	89.63%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.47%	95.56%
CHEMBL253	P34972	Cannabinoid CB2 receptor	91.02%	97.25%
CHEMBL3137262	O60341	LSD1/CoREST complex	83.79%	97.09%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	83.72%	97.14%
CHEMBL2069156	Q14145	Kelch-like ECH-associated protein 1	81.29%	82.38%
CHEMBL4227	P25090	Lipoxin A4 receptor	80.17%	100.00%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 9864227
• LOTUS: LTS0082205
• wikiData: Q77381778