(1R,2R,4S,7S,12R,13S,16Z)-25-(6-hydroxy-9H-pyrido[3,4-b]indol-1-yl)-28-oxa-11,22-diazahexacyclo[11.11.2.12,22.14,7.02,12.04,11]octacosa-16,25-dien-13-ol

Details

• Internal ID: 290536cb-e1bd-43cf-b745-bb402c5d9003
• Taxonomy: Alkaloids and derivatives > Harmala alkaloids
• IUPAC Name: (1R,2R,4S,7S,12R,13S,16Z)-25-(6-hydroxy-9H-pyrido[3,4-b]indol-1-yl)-28-oxa-11,22-diazahexacyclo[11.11.2.12,22.14,7.02,12.04,11]octacosa-16,25-dien-13-ol
• InChI: InChI=1S/C36H44N4O3/c41-24-9-10-30-27(20-24)26-12-16-37-31(32(26)38-30)28-21-35(42)14-5-3-1-2-4-6-17-39-19-13-29(28)34(23-39)22-36-15-11-25(43-36)8-7-18-40(36)33(34)35/h1,3,9-10,12,16,20-21,25,29,33,38,41-42H,2,4-8,11,13-15,17-19,22-23H2/b3-1-/t25-,29-,33+,34-,35-,36-/m0/s1
• InChI Key: YFLBQKLEXJGASL-VIRHFZLLSA-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: 4.80
• Atomic LogP (AlogP): 6.12
• 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	+	0.9890	98.90%
Caco-2	-	0.8481	84.81%
Blood Brain Barrier	+	0.6000	60.00%
Human oral bioavailability	-	0.5857	58.57%
Subcellular localzation	Mitochondria	0.6426	64.26%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8283	82.83%
OATP1B3 inhibitior	+	0.9435	94.35%
MATE1 inhibitior	-	0.8600	86.00%
OCT2 inhibitior	-	0.5500	55.00%
BSEP inhibitior	+	0.9941	99.41%
P-glycoprotein inhibitior	+	0.8428	84.28%
P-glycoprotein substrate	+	0.7985	79.85%
CYP3A4 substrate	+	0.7243	72.43%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.6948	69.48%
CYP3A4 inhibition	+	0.6980	69.80%
CYP2C9 inhibition	-	0.7034	70.34%
CYP2C19 inhibition	-	0.5454	54.54%
CYP2D6 inhibition	-	0.7783	77.83%
CYP1A2 inhibition	-	0.7377	73.77%
CYP2C8 inhibition	+	0.8398	83.98%
CYP inhibitory promiscuity	-	0.5348	53.48%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.6172	61.72%
Eye corrosion	-	0.9871	98.71%
Eye irritation	-	0.9485	94.85%
Skin irritation	-	0.7554	75.54%
Skin corrosion	-	0.9221	92.21%
Ames mutagenesis	-	0.5300	53.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5089	50.89%
Micronuclear	+	0.7800	78.00%
Hepatotoxicity	-	0.5375	53.75%
skin sensitisation	-	0.8417	84.17%
Respiratory toxicity	+	0.8222	82.22%
Reproductive toxicity	+	0.9667	96.67%
Mitochondrial toxicity	+	0.9500	95.00%
Nephrotoxicity	-	0.9338	93.38%
Acute Oral Toxicity (c)	III	0.5741	57.41%
Estrogen receptor binding	+	0.8148	81.48%
Androgen receptor binding	+	0.7883	78.83%
Thyroid receptor binding	+	0.5906	59.06%
Glucocorticoid receptor binding	+	0.6687	66.87%
Aromatase binding	+	0.6771	67.71%
PPAR gamma	+	0.6693	66.93%
Honey bee toxicity	-	0.7656	76.56%
Biodegradation	-	0.9250	92.50%
Crustacea aquatic toxicity	+	0.6600	66.00%
Fish aquatic toxicity	+	0.6481	64.81%

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	99.52%	91.11%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	99.09%	85.14%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	97.38%	94.45%
CHEMBL2107	P61073	C-X-C chemokine receptor type 4	96.99%	93.10%
CHEMBL1806	P11388	DNA topoisomerase II alpha	96.66%	89.00%
CHEMBL6175	Q9H3R0	Lysine-specific demethylase 4C	96.05%	96.69%
CHEMBL241	Q14432	Phosphodiesterase 3A	95.21%	92.94%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.71%	96.09%
CHEMBL3192	Q9BY41	Histone deacetylase 8	93.78%	93.99%
CHEMBL213	P08588	Beta-1 adrenergic receptor	92.97%	95.56%
CHEMBL2094127	P06493	Cyclin-dependent kinase 1/cyclin B	92.14%	96.00%
CHEMBL3310	Q96DB2	Histone deacetylase 11	92.12%	88.56%
CHEMBL1163125	O60885	Bromodomain-containing protein 4	91.46%	97.31%
CHEMBL2095226	P05556	Integrin alpha-5/beta-1	90.90%	96.39%
CHEMBL4145	Q9UKV0	Histone deacetylase 9	90.80%	85.49%
CHEMBL5203	P33316	dUTP pyrophosphatase	90.72%	99.18%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	90.67%	94.00%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	90.36%	91.71%
CHEMBL3137262	O60341	LSD1/CoREST complex	90.06%	97.09%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	89.48%	95.78%
CHEMBL3155	P34969	Serotonin 7 (5-HT7) receptor	89.46%	90.71%
CHEMBL5608	Q16288	NT-3 growth factor receptor	89.10%	95.89%
CHEMBL5103	Q969S8	Histone deacetylase 10	88.08%	90.08%
CHEMBL4101	P17612	cAMP-dependent protein kinase alpha-catalytic subunit	87.07%	82.86%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	86.05%	99.23%
CHEMBL253	P34972	Cannabinoid CB2 receptor	85.38%	97.25%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	85.25%	94.62%
CHEMBL2581	P07339	Cathepsin D	84.14%	98.95%
CHEMBL325	Q13547	Histone deacetylase 1	83.77%	95.92%
CHEMBL1821	P08173	Muscarinic acetylcholine receptor M4	83.61%	94.08%
CHEMBL3553	P29597	Tyrosine-protein kinase TYK2	83.43%	97.09%
CHEMBL2781	P19634	Sodium/hydrogen exchanger 1	83.32%	90.24%
CHEMBL5646	Q6L5J4	FML2_HUMAN	83.08%	100.00%
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	82.74%	95.17%
CHEMBL4208	P20618	Proteasome component C5	82.47%	90.00%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	82.05%	99.15%
CHEMBL1994	P08235	Mineralocorticoid receptor	81.84%	100.00%
CHEMBL3384	Q16512	Protein kinase N1	81.03%	80.71%
CHEMBL1937	Q92769	Histone deacetylase 2	80.95%	94.75%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	80.48%	92.62%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 101855965
• LOTUS: LTS0040670
• wikiData: Q105347651