(R)-1-[5-[[(S)-3,3-Dimethyloxiran-2-yl]methyl]-1H-indol-3-yl]-3-methylbutane-2,3-diol

Details

• Internal ID: dd24b19e-0638-447a-939a-523c3513aa33
• Taxonomy: Organoheterocyclic compounds > Indoles and derivatives > Indoles > 3-alkylindoles
• IUPAC Name: (2R)-1-[5-[[(2S)-3,3-dimethyloxiran-2-yl]methyl]-1H-indol-3-yl]-3-methylbutane-2,3-diol
• SMILES (Canonical): CC1(C(O1)CC2=CC3=C(C=C2)NC=C3CC(C(C)(C)O)O)C
• SMILES (Isomeric): CC1([C@@H](O1)CC2=CC3=C(C=C2)NC=C3C[C@H](C(C)(C)O)O)C
• InChI: InChI=1S/C18H25NO3/c1-17(2,21)15(20)9-12-10-19-14-6-5-11(7-13(12)14)8-16-18(3,4)22-16/h5-7,10,15-16,19-21H,8-9H2,1-4H3/t15-,16+/m1/s1
• InChI Key: HXYYXPJRHVMUQY-CVEARBPZSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₈H₂₅NO₃
• Molecular Weight: 303.40 g/mol
• Exact Mass: 303.18344366 g/mol
• Topological Polar Surface Area (TPSA): 68.80 Ų
• XlogP: 2.20
• Atomic LogP (AlogP): 2.56
• H-Bond Acceptor: 3
• H-Bond Donor: 3
• Rotatable Bonds: 5

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9820	98.20%
Caco-2	-	0.5239	52.39%
Blood Brain Barrier	+	0.6250	62.50%
Human oral bioavailability	-	0.5286	52.86%
Subcellular localzation	Lysosomes	0.3933	39.33%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9142	91.42%
OATP1B3 inhibitior	+	0.9418	94.18%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	-	0.4692	46.92%
P-glycoprotein inhibitior	-	0.9162	91.62%
P-glycoprotein substrate	+	0.5243	52.43%
CYP3A4 substrate	+	0.5532	55.32%
CYP2C9 substrate	-	0.5979	59.79%
CYP2D6 substrate	-	0.7041	70.41%
CYP3A4 inhibition	-	0.7022	70.22%
CYP2C9 inhibition	-	0.7907	79.07%
CYP2C19 inhibition	-	0.5985	59.85%
CYP2D6 inhibition	-	0.8666	86.66%
CYP1A2 inhibition	-	0.5829	58.29%
CYP2C8 inhibition	+	0.4763	47.63%
CYP inhibitory promiscuity	-	0.5456	54.56%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.8600	86.00%
Carcinogenicity (trinary)	Non-required	0.5386	53.86%
Eye corrosion	-	0.9903	99.03%
Eye irritation	-	0.8675	86.75%
Skin irritation	-	0.7302	73.02%
Skin corrosion	-	0.9042	90.42%
Ames mutagenesis	-	0.6000	60.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4235	42.35%
Micronuclear	+	0.5300	53.00%
Hepatotoxicity	-	0.8500	85.00%
skin sensitisation	-	0.7517	75.17%
Respiratory toxicity	+	0.7222	72.22%
Reproductive toxicity	+	0.7889	78.89%
Mitochondrial toxicity	+	0.7625	76.25%
Nephrotoxicity	-	0.9072	90.72%
Acute Oral Toxicity (c)	III	0.5484	54.84%
Estrogen receptor binding	+	0.7808	78.08%
Androgen receptor binding	-	0.5624	56.24%
Thyroid receptor binding	+	0.6503	65.03%
Glucocorticoid receptor binding	+	0.6483	64.83%
Aromatase binding	+	0.6561	65.61%
PPAR gamma	+	0.7683	76.83%
Honey bee toxicity	-	0.7549	75.49%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.6400	64.00%
Fish aquatic toxicity	-	0.4255	42.55%

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	98.83%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	97.40%	94.45%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.42%	96.09%
CHEMBL4040	P28482	MAP kinase ERK2	95.84%	83.82%
CHEMBL2581	P07339	Cathepsin D	95.62%	98.95%
CHEMBL1907605	P24864	Cyclin-dependent kinase 2/cyclin E1	93.43%	92.88%
CHEMBL253	P34972	Cannabinoid CB2 receptor	92.85%	97.25%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	90.40%	85.14%
CHEMBL5608	Q16288	NT-3 growth factor receptor	89.94%	95.89%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	89.76%	92.62%
CHEMBL2535	P11166	Glucose transporter	88.68%	98.75%
CHEMBL213	P08588	Beta-1 adrenergic receptor	88.55%	95.56%
CHEMBL3837	P07711	Cathepsin L	87.77%	96.61%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	87.52%	94.00%
CHEMBL215	P09917	Arachidonate 5-lipoxygenase	86.49%	92.68%
CHEMBL4051	P13569	Cystic fibrosis transmembrane conductance regulator	86.49%	95.71%
CHEMBL1951	P21397	Monoamine oxidase A	85.94%	91.49%
CHEMBL3401	O75469	Pregnane X receptor	84.89%	94.73%
CHEMBL1806	P11388	DNA topoisomerase II alpha	84.70%	89.00%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	82.57%	96.90%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	82.48%	89.62%
CHEMBL3137262	O60341	LSD1/CoREST complex	82.32%	97.09%
CHEMBL255	P29275	Adenosine A2b receptor	81.31%	98.59%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	80.89%	95.56%

Plants that contains it

• Hexalobus crispiflorus
• Xanthium strumarium subsp. strumarium

Cross-Links

• PubChem: 10357624
• NPASS: NPC185411
• LOTUS: LTS0256124
• wikiData: Q105035203