(1R,2R,4R,5Z,12R,13S,16E)-25-(6-hydroxy-4,9-dihydro-3H-pyrido[3,4-b]indol-1-yl)-11,22-diazapentacyclo[11.11.2.12,22.02,12.04,11]heptacosa-5,16,25-trien-13-ol

Details

• Internal ID: a5db5949-8589-4472-91ff-643e4e16c9c3
• Taxonomy: Alkaloids and derivatives > Harmala alkaloids
• IUPAC Name: (1R,2R,4R,5Z,12R,13S,16E)-25-(6-hydroxy-4,9-dihydro-3H-pyrido[3,4-b]indol-1-yl)-11,22-diazapentacyclo[11.11.2.12,22.02,12.04,11]heptacosa-5,16,25-trien-13-ol
• SMILES (Canonical): C1CCN2CCC3C(=CC(CCC=CC1)(C4C3(C2)CC5N4CCCCC=C5)O)C6=NCCC7=C6NC8=C7C=C(C=C8)O
• SMILES (Isomeric): C1CCN2CC[C@H]3C(=C[C@@](CC/C=C/C1)([C@H]4[C@]3(C2)C[C@H]/5N4CCCC/C=C5)O)C6=NCCC7=C6NC8=C7C=C(C=C8)O
• InChI: InChI=1S/C36H46N4O2/c41-26-12-13-31-28(21-26)27-14-17-37-32(33(27)38-31)29-23-36(42)16-8-4-1-2-5-9-18-39-20-15-30(29)35(24-39)22-25-11-7-3-6-10-19-40(25)34(35)36/h1,4,7,11-13,21,23,25,30,34,38,41-42H,2-3,5-6,8-10,14-20,22,24H2/b4-1+,11-7-/t25-,30-,34+,35-,36-/m0/s1
• InChI Key: ULEDZCZHECPVBC-CMEJLQAVSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₆H₄₆N₄O₂
• Molecular Weight: 566.80 g/mol
• Exact Mass: 566.36207672 g/mol
• Topological Polar Surface Area (TPSA): 75.10 Ų
• XlogP: 5.30
• Atomic LogP (AlogP): 5.90
• H-Bond Acceptor: 5
• H-Bond Donor: 3
• Rotatable Bonds: 1

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9918	99.18%
Caco-2	-	0.8250	82.50%
Blood Brain Barrier	+	0.8507	85.07%
Human oral bioavailability	-	0.5857	58.57%
Subcellular localzation	Mitochondria	0.7950	79.50%
OATP2B1 inhibitior	-	0.8594	85.94%
OATP1B1 inhibitior	+	0.8343	83.43%
OATP1B3 inhibitior	+	0.9405	94.05%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	+	0.7000	70.00%
BSEP inhibitior	+	0.9842	98.42%
P-glycoprotein inhibitior	+	0.8521	85.21%
P-glycoprotein substrate	+	0.7684	76.84%
CYP3A4 substrate	+	0.7097	70.97%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.7314	73.14%
CYP3A4 inhibition	-	0.6039	60.39%
CYP2C9 inhibition	-	0.7783	77.83%
CYP2C19 inhibition	-	0.7591	75.91%
CYP2D6 inhibition	-	0.6484	64.84%
CYP1A2 inhibition	-	0.6162	61.62%
CYP2C8 inhibition	+	0.7072	70.72%
CYP inhibitory promiscuity	-	0.5572	55.72%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.6334	63.34%
Eye corrosion	-	0.9865	98.65%
Eye irritation	-	0.9450	94.50%
Skin irritation	-	0.7311	73.11%
Skin corrosion	-	0.9111	91.11%
Ames mutagenesis	-	0.5300	53.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5141	51.41%
Micronuclear	+	0.7200	72.00%
Hepatotoxicity	+	0.5024	50.24%
skin sensitisation	-	0.8197	81.97%
Respiratory toxicity	+	0.8111	81.11%
Reproductive toxicity	+	0.9556	95.56%
Mitochondrial toxicity	+	0.9250	92.50%
Nephrotoxicity	-	0.8709	87.09%
Acute Oral Toxicity (c)	III	0.5511	55.11%
Estrogen receptor binding	+	0.8025	80.25%
Androgen receptor binding	+	0.7661	76.61%
Thyroid receptor binding	+	0.5594	55.94%
Glucocorticoid receptor binding	+	0.5839	58.39%
Aromatase binding	+	0.5812	58.12%
PPAR gamma	+	0.6787	67.87%
Honey bee toxicity	-	0.7929	79.29%
Biodegradation	-	0.9250	92.50%
Crustacea aquatic toxicity	+	0.6500	65.00%
Fish aquatic toxicity	-	0.3790	37.90%

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	99.12%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	98.14%	94.45%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.40%	96.09%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	95.63%	91.71%
CHEMBL5608	Q16288	NT-3 growth factor receptor	92.92%	95.89%
CHEMBL2581	P07339	Cathepsin D	92.74%	98.95%
CHEMBL2107	P61073	C-X-C chemokine receptor type 4	92.59%	93.10%
CHEMBL3310	Q96DB2	Histone deacetylase 11	92.58%	88.56%
CHEMBL3155	P34969	Serotonin 7 (5-HT7) receptor	92.29%	90.71%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	91.96%	85.14%
CHEMBL4145	Q9UKV0	Histone deacetylase 9	91.52%	85.49%
CHEMBL5103	Q969S8	Histone deacetylase 10	91.34%	90.08%
CHEMBL2095226	P05556	Integrin alpha-5/beta-1	90.58%	96.39%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	90.09%	93.40%
CHEMBL3137262	O60341	LSD1/CoREST complex	90.05%	97.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.93%	95.56%
CHEMBL241	Q14432	Phosphodiesterase 3A	87.74%	92.94%
CHEMBL213	P08588	Beta-1 adrenergic receptor	87.67%	95.56%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	87.39%	93.04%
CHEMBL2782	P35610	Acyl coenzyme A:cholesterol acyltransferase 1	86.26%	91.65%
CHEMBL5203	P33316	dUTP pyrophosphatase	86.17%	99.18%
CHEMBL2535	P11166	Glucose transporter	86.13%	98.75%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	85.57%	96.21%
CHEMBL253	P34972	Cannabinoid CB2 receptor	84.61%	97.25%
CHEMBL242	Q92731	Estrogen receptor beta	84.02%	98.35%
CHEMBL2041	P07949	Tyrosine-protein kinase receptor RET	83.98%	91.79%
CHEMBL240	Q12809	HERG	83.55%	89.76%
CHEMBL206	P03372	Estrogen receptor alpha	82.27%	97.64%
CHEMBL2140	P48775	Tryptophan 2,3-dioxygenase	82.21%	98.46%
CHEMBL1806	P11388	DNA topoisomerase II alpha	82.04%	89.00%
CHEMBL3922	P50579	Methionine aminopeptidase 2	81.94%	97.28%
CHEMBL5646	Q6L5J4	FML2_HUMAN	81.93%	100.00%
CHEMBL2094127	P06493	Cyclin-dependent kinase 1/cyclin B	81.64%	96.00%
CHEMBL1994	P08235	Mineralocorticoid receptor	81.59%	100.00%
CHEMBL4208	P20618	Proteasome component C5	81.15%	90.00%
CHEMBL2781	P19634	Sodium/hydrogen exchanger 1	80.81%	90.24%
CHEMBL1821	P08173	Muscarinic acetylcholine receptor M4	80.71%	94.08%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	80.31%	92.62%
CHEMBL217	P14416	Dopamine D2 receptor	80.19%	95.62%
CHEMBL4073	P09237	Matrix metalloproteinase 7	80.02%	97.56%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 163194537
• LOTUS: LTS0262110
• wikiData: Q105275052