Hapalindolinone B

Details

• Internal ID: ce474ae8-c202-4767-b0e4-48f72554815e
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Sesquiterpenoids
• IUPAC Name: (1'R,2'S,3R,5'R,6'S)-2'-ethenyl-2'-methyl-2-oxo-5'-prop-1-en-2-ylspiro[1H-indole-3,7'-bicyclo[4.1.0]heptane]-1'-carbonitrile
• InChI: InChI=1S/C21H22N2O/c1-5-19(4)11-10-14(13(2)3)17-20(19,12-22)21(17)15-8-6-7-9-16(15)23-18(21)24/h5-9,14,17H,1-2,10-11H2,3-4H3,(H,23,24)/t14-,17-,19+,20-,21+/m0/s1
• InChI Key: OIBWFYOBXWQXKY-UBFQGWSASA-N
• Popularity: 6 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₂₂N₂O
• Molecular Weight: 318.40 g/mol
• Exact Mass: 318.173213330 g/mol
• Topological Polar Surface Area (TPSA): 52.90 Ų
• XlogP: 4.00
• Atomic LogP (AlogP): 4.19
• H-Bond Acceptor: 2
• H-Bond Donor: 1
• Rotatable Bonds: 2

Synonyms

• DTXSID901047311

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9964	99.64%
Caco-2	-	0.6314	63.14%
Blood Brain Barrier	+	0.9500	95.00%
Human oral bioavailability	+	0.6000	60.00%
Subcellular localzation	Plasma membrane	0.4076	40.76%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9049	90.49%
OATP1B3 inhibitior	+	0.9380	93.80%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.6750	67.50%
BSEP inhibitior	+	0.6275	62.75%
P-glycoprotein inhibitior	-	0.8073	80.73%
P-glycoprotein substrate	-	0.6974	69.74%
CYP3A4 substrate	+	0.6359	63.59%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8079	80.79%
CYP3A4 inhibition	+	0.8010	80.10%
CYP2C9 inhibition	+	0.7496	74.96%
CYP2C19 inhibition	+	0.7162	71.62%
CYP2D6 inhibition	-	0.6168	61.68%
CYP1A2 inhibition	+	0.6872	68.72%
CYP2C8 inhibition	+	0.5000	50.00%
CYP inhibitory promiscuity	+	0.8099	80.99%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.8600	86.00%
Carcinogenicity (trinary)	Non-required	0.4625	46.25%
Eye corrosion	-	0.9813	98.13%
Eye irritation	-	0.9890	98.90%
Skin irritation	-	0.7586	75.86%
Skin corrosion	-	0.9317	93.17%
Ames mutagenesis	-	0.7000	70.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6676	66.76%
Micronuclear	+	0.5200	52.00%
Hepatotoxicity	+	0.5680	56.80%
skin sensitisation	-	0.7708	77.08%
Respiratory toxicity	+	0.7333	73.33%
Reproductive toxicity	+	0.5889	58.89%
Mitochondrial toxicity	+	0.6250	62.50%
Nephrotoxicity	+	0.7102	71.02%
Acute Oral Toxicity (c)	III	0.5276	52.76%
Estrogen receptor binding	+	0.7603	76.03%
Androgen receptor binding	+	0.7140	71.40%
Thyroid receptor binding	+	0.6937	69.37%
Glucocorticoid receptor binding	+	0.7714	77.14%
Aromatase binding	+	0.7939	79.39%
PPAR gamma	+	0.7513	75.13%
Honey bee toxicity	-	0.8529	85.29%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.5400	54.00%
Fish aquatic toxicity	+	0.9872	98.72%

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	98.55%	91.11%
CHEMBL2581	P07339	Cathepsin D	96.53%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.78%	95.56%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	90.83%	96.09%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	90.65%	82.69%
CHEMBL221	P23219	Cyclooxygenase-1	89.34%	90.17%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	87.06%	94.62%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	86.67%	99.23%
CHEMBL253	P34972	Cannabinoid CB2 receptor	86.00%	97.25%
CHEMBL1994	P08235	Mineralocorticoid receptor	85.94%	100.00%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	85.72%	94.80%
CHEMBL1806	P11388	DNA topoisomerase II alpha	81.55%	89.00%
CHEMBL4208	P20618	Proteasome component C5	81.45%	90.00%
CHEMBL1821	P08173	Muscarinic acetylcholine receptor M4	80.87%	94.08%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 139588041
• LOTUS: LTS0087926
• wikiData: Q104246456