(3aR)-1-Methyl-3aalpha-(1,1-dimethyl-2-propenyl)-5-prenyl-6-bromo-1,2,3,3a,8,8aalpha-hexahydropyrrolo[2,3-b]indole

Details

• Internal ID: 0df478d3-5f21-460e-9101-0b54caba1bf5
• Taxonomy: Organoheterocyclic compounds > Indoles and derivatives > Pyrroloindoles
• IUPAC Name: (3aS,8bR)-6-bromo-3-methyl-8b-(2-methylbut-3-en-2-yl)-7-(3-methylbut-2-enyl)-1,2,3a,4-tetrahydropyrrolo[2,3-b]indole
• SMILES (Canonical): CC(=CCC1=CC2=C(C=C1Br)NC3C2(CCN3C)C(C)(C)C=C)C
• SMILES (Isomeric): CC(=CCC1=CC2=C(C=C1Br)N[C@@H]3[C@]2(CCN3C)C(C)(C)C=C)C
• InChI: InChI=1S/C21H29BrN2/c1-7-20(4,5)21-10-11-24(6)19(21)23-18-13-17(22)15(12-16(18)21)9-8-14(2)3/h7-8,12-13,19,23H,1,9-11H2,2-6H3/t19-,21+/m0/s1
• InChI Key: FGDLDCKUPXVIGT-PZJWPPBQSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₂₉BrN₂
• Molecular Weight: 389.40 g/mol
• Exact Mass: 388.15141 g/mol
• Topological Polar Surface Area (TPSA): 15.30 Ų
• XlogP: 6.70
• Atomic LogP (AlogP): 5.49
• H-Bond Acceptor: 2
• H-Bond Donor: 1
• Rotatable Bonds: 4

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9859	98.59%
Caco-2	+	0.6641	66.41%
Blood Brain Barrier	+	0.9250	92.50%
Human oral bioavailability	+	0.5286	52.86%
Subcellular localzation	Lysosomes	0.5684	56.84%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8823	88.23%
OATP1B3 inhibitior	+	0.9382	93.82%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	+	0.6250	62.50%
BSEP inhibitior	+	0.6468	64.68%
P-glycoprotein inhibitior	-	0.6862	68.62%
P-glycoprotein substrate	+	0.5852	58.52%
CYP3A4 substrate	+	0.6260	62.60%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.7040	70.40%
CYP3A4 inhibition	-	0.7961	79.61%
CYP2C9 inhibition	-	0.7422	74.22%
CYP2C19 inhibition	-	0.6342	63.42%
CYP2D6 inhibition	-	0.6829	68.29%
CYP1A2 inhibition	-	0.5179	51.79%
CYP2C8 inhibition	-	0.7792	77.92%
CYP inhibitory promiscuity	+	0.6205	62.05%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.8822	88.22%
Carcinogenicity (trinary)	Non-required	0.6380	63.80%
Eye corrosion	-	0.9831	98.31%
Eye irritation	-	0.9689	96.89%
Skin irritation	-	0.7331	73.31%
Skin corrosion	-	0.8633	86.33%
Ames mutagenesis	-	0.6900	69.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8354	83.54%
Micronuclear	-	0.5400	54.00%
Hepatotoxicity	+	0.6427	64.27%
skin sensitisation	-	0.7944	79.44%
Respiratory toxicity	+	0.7222	72.22%
Reproductive toxicity	+	0.8000	80.00%
Mitochondrial toxicity	+	0.8500	85.00%
Nephrotoxicity	-	0.7829	78.29%
Acute Oral Toxicity (c)	III	0.5732	57.32%
Estrogen receptor binding	+	0.6862	68.62%
Androgen receptor binding	+	0.6575	65.75%
Thyroid receptor binding	+	0.8294	82.94%
Glucocorticoid receptor binding	+	0.6433	64.33%
Aromatase binding	+	0.6154	61.54%
PPAR gamma	+	0.7213	72.13%
Honey bee toxicity	-	0.8182	81.82%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	+	0.5100	51.00%
Fish aquatic toxicity	+	0.9913	99.13%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL253	P34972	Cannabinoid CB2 receptor	98.40%	97.25%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.02%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.92%	91.11%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	93.32%	93.40%
CHEMBL2581	P07339	Cathepsin D	93.12%	98.95%
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	92.69%	95.17%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	92.05%	94.45%
CHEMBL5469	Q14289	Protein tyrosine kinase 2 beta	89.70%	91.03%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	87.87%	89.62%
CHEMBL241	Q14432	Phosphodiesterase 3A	87.85%	92.94%
CHEMBL5608	Q16288	NT-3 growth factor receptor	87.37%	95.89%
CHEMBL2781	P19634	Sodium/hydrogen exchanger 1	86.68%	90.24%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	86.38%	93.00%
CHEMBL4208	P20618	Proteasome component C5	86.26%	90.00%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	86.13%	93.04%
CHEMBL1937	Q92769	Histone deacetylase 2	86.07%	94.75%
CHEMBL1994	P08235	Mineralocorticoid receptor	84.95%	100.00%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	83.87%	91.24%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	83.78%	95.50%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	83.26%	85.14%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	83.19%	95.56%
CHEMBL4506	Q96EB6	NAD-dependent deacetylase sirtuin 1	82.95%	88.33%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	82.20%	91.07%
CHEMBL3137262	O60341	LSD1/CoREST complex	81.20%	97.09%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	80.67%	93.03%
CHEMBL1293249	Q13887	Kruppel-like factor 5	80.45%	86.33%

Plants that contains it

• Conospermum sphacelatum

Cross-Links

• PubChem: 21674200
• LOTUS: LTS0252979
• wikiData: Q105211578