(1R,2R,4R,7R,8S,12R,13S)-25-(9H-pyrido[3,4-b]indol-1-yl)-28-oxa-11,22-diazahexacyclo[11.11.2.12,22.14,8.02,12.04,11]octacosa-16,25-diene-7,13-diol

Details

• Internal ID: 24b385dc-1489-4900-bd1c-1dc223929141
• Taxonomy: Alkaloids and derivatives > Harmala alkaloids
• IUPAC Name: (1R,2R,4R,7R,8S,12R,13S)-25-(9H-pyrido[3,4-b]indol-1-yl)-28-oxa-11,22-diazahexacyclo[11.11.2.12,22.14,8.02,12.04,11]octacosa-16,25-diene-7,13-diol
• InChI: InChI=1S/C36H44N4O3/c41-29-11-16-36-22-34-23-39-18-8-4-2-1-3-7-15-35(42,33(34)40(36)20-14-30(29)43-36)21-26(27(34)13-19-39)31-32-25(12-17-37-31)24-9-5-6-10-28(24)38-32/h1,3,5-6,9-10,12,17,21,27,29-30,33,38,41-42H,2,4,7-8,11,13-16,18-20,22-23H2/t27-,29+,30-,33+,34-,35-,36+/m0/s1
• InChI Key: BKEROKGINJVXMS-PJOPPWRVSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₆H₄₄N₄O₃
• Molecular Weight: 580.80 g/mol
• Exact Mass: 580.34134128 g/mol
• Topological Polar Surface Area (TPSA): 84.90 Ų
• XlogP: 4.10
• Atomic LogP (AlogP): 5.39
• H-Bond Acceptor: 6
• 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	+	0.9875	98.75%
Caco-2	-	0.8576	85.76%
Blood Brain Barrier	+	0.6500	65.00%
Human oral bioavailability	+	0.5143	51.43%
Subcellular localzation	Mitochondria	0.6502	65.02%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8516	85.16%
OATP1B3 inhibitior	+	0.9416	94.16%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.7000	70.00%
BSEP inhibitior	+	0.9881	98.81%
P-glycoprotein inhibitior	+	0.8376	83.76%
P-glycoprotein substrate	+	0.7431	74.31%
CYP3A4 substrate	+	0.7235	72.35%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.6852	68.52%
CYP3A4 inhibition	-	0.6791	67.91%
CYP2C9 inhibition	-	0.7540	75.40%
CYP2C19 inhibition	-	0.6437	64.37%
CYP2D6 inhibition	-	0.7628	76.28%
CYP1A2 inhibition	-	0.7198	71.98%
CYP2C8 inhibition	+	0.7918	79.18%
CYP inhibitory promiscuity	-	0.6926	69.26%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9400	94.00%
Carcinogenicity (trinary)	Non-required	0.5797	57.97%
Eye corrosion	-	0.9880	98.80%
Eye irritation	-	0.9528	95.28%
Skin irritation	-	0.7563	75.63%
Skin corrosion	-	0.9227	92.27%
Ames mutagenesis	-	0.5100	51.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.3853	38.53%
Micronuclear	+	0.8300	83.00%
Hepatotoxicity	+	0.5301	53.01%
skin sensitisation	-	0.8465	84.65%
Respiratory toxicity	+	0.8778	87.78%
Reproductive toxicity	+	0.9667	96.67%
Mitochondrial toxicity	+	0.9625	96.25%
Nephrotoxicity	-	0.9127	91.27%
Acute Oral Toxicity (c)	III	0.5700	57.00%
Estrogen receptor binding	+	0.8002	80.02%
Androgen receptor binding	+	0.7754	77.54%
Thyroid receptor binding	+	0.5504	55.04%
Glucocorticoid receptor binding	+	0.6509	65.09%
Aromatase binding	+	0.6432	64.32%
PPAR gamma	+	0.6469	64.69%
Honey bee toxicity	-	0.7787	77.87%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	+	0.6000	60.00%
Fish aquatic toxicity	-	0.5326	53.26%

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	98.62%	91.11%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	98.37%	85.14%
CHEMBL1806	P11388	DNA topoisomerase II alpha	95.19%	89.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.74%	96.09%
CHEMBL3310	Q96DB2	Histone deacetylase 11	93.33%	88.56%
CHEMBL2094127	P06493	Cyclin-dependent kinase 1/cyclin B	93.10%	96.00%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	93.04%	94.62%
CHEMBL3192	Q9BY41	Histone deacetylase 8	92.36%	93.99%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	92.25%	94.45%
CHEMBL2095226	P05556	Integrin alpha-5/beta-1	91.36%	96.39%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	90.36%	99.23%
CHEMBL1821	P08173	Muscarinic acetylcholine receptor M4	90.13%	94.08%
CHEMBL240	Q12809	HERG	89.30%	89.76%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	89.22%	94.00%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	88.86%	91.71%
CHEMBL216	P11229	Muscarinic acetylcholine receptor M1	87.16%	94.23%
CHEMBL241	Q14432	Phosphodiesterase 3A	86.28%	92.94%
CHEMBL3137262	O60341	LSD1/CoREST complex	86.27%	97.09%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	86.20%	95.83%
CHEMBL213	P08588	Beta-1 adrenergic receptor	86.13%	95.56%
CHEMBL2107	P61073	C-X-C chemokine receptor type 4	85.77%	93.10%
CHEMBL253	P34972	Cannabinoid CB2 receptor	85.67%	97.25%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	85.49%	92.62%
CHEMBL2693	Q9UIQ6	Cystinyl aminopeptidase	85.28%	97.64%
CHEMBL218	P21554	Cannabinoid CB1 receptor	84.79%	96.61%
CHEMBL2378	P30307	Dual specificity phosphatase Cdc25C	84.76%	96.67%
CHEMBL4302	P08183	P-glycoprotein 1	84.19%	92.98%
CHEMBL3155	P34969	Serotonin 7 (5-HT7) receptor	84.10%	90.71%
CHEMBL5646	Q6L5J4	FML2_HUMAN	83.81%	100.00%
CHEMBL1163125	O60885	Bromodomain-containing protein 4	83.61%	97.31%
CHEMBL5103	Q969S8	Histone deacetylase 10	82.86%	90.08%
CHEMBL4227	P25090	Lipoxin A4 receptor	82.19%	100.00%
CHEMBL3475	P05121	Plasminogen activator inhibitor-1	81.90%	83.00%
CHEMBL4101	P17612	cAMP-dependent protein kinase alpha-catalytic subunit	81.46%	82.86%
CHEMBL4208	P20618	Proteasome component C5	80.99%	90.00%
CHEMBL1795139	Q8IU80	Transmembrane protease serine 6	80.96%	98.33%
CHEMBL4145	Q9UKV0	Histone deacetylase 9	80.78%	85.49%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.72%	95.89%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 162818993
• LOTUS: LTS0227575
• wikiData: Q104937528