(1R,2R,8Z,12R,13S,21E,26S,27S)-27-[(1R)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indol-1-yl]-25-oxa-3,16-diazapentacyclo[11.11.3.112,16.01,26.02,12]octacosa-8,21-diene

Details

• Internal ID: 4b50f6ec-f2c7-4e71-ad3e-209b445c3153
• Taxonomy: Alkaloids and derivatives > Harmala alkaloids
• IUPAC Name: (1R,2R,8Z,12R,13S,21E,26S,27S)-27-[(1R)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indol-1-yl]-25-oxa-3,16-diazapentacyclo[11.11.3.112,16.01,26.02,12]octacosa-8,21-diene
• SMILES (Canonical): C1CCNC2C3(CCC=CC1)CN4CCCCC=CCCC25C(O5)C(C3CC4)C6C7=C(CCN6)C8=CC=CC=C8N7
• SMILES (Isomeric): C1CCN[C@@H]2[C@@]3(CC/C=C\C1)CN4CCCC/C=C/CC[C@]25[C@@H](O5)[C@@H]([C@@H]3CC4)[C@@H]6C7=C(CCN6)C8=CC=CC=C8N7
• InChI: InChI=1S/C36H50N4O/c1-3-7-13-21-38-34-35(19-11-5-1)25-40-23-14-8-4-2-6-12-20-36(34)33(41-36)30(28(35)18-24-40)32-31-27(17-22-37-32)26-15-9-10-16-29(26)39-31/h1-2,5-6,9-10,15-16,28,30,32-34,37-39H,3-4,7-8,11-14,17-25H2/b5-1-,6-2+/t28-,30-,32+,33-,34+,35-,36-/m0/s1
• InChI Key: NNZHASOWBAIFFH-NTBUGXPYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₆H₅₀N₄O
• Molecular Weight: 554.80 g/mol
• Exact Mass: 554.39846223 g/mol
• Topological Polar Surface Area (TPSA): 55.60 Ų
• XlogP: 5.80
• Atomic LogP (AlogP): 6.43
• H-Bond Acceptor: 4
• 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	+	0.9855	98.55%
Caco-2	-	0.7820	78.20%
Blood Brain Barrier	+	0.9379	93.79%
Human oral bioavailability	-	0.5857	58.57%
Subcellular localzation	Lysosomes	0.4582	45.82%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8537	85.37%
OATP1B3 inhibitior	+	0.9431	94.31%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.5500	55.00%
BSEP inhibitior	+	0.9838	98.38%
P-glycoprotein inhibitior	+	0.8014	80.14%
P-glycoprotein substrate	+	0.6201	62.01%
CYP3A4 substrate	+	0.7034	70.34%
CYP2C9 substrate	-	0.8042	80.42%
CYP2D6 substrate	+	0.4133	41.33%
CYP3A4 inhibition	+	0.5000	50.00%
CYP2C9 inhibition	-	0.7857	78.57%
CYP2C19 inhibition	-	0.7086	70.86%
CYP2D6 inhibition	-	0.5479	54.79%
CYP1A2 inhibition	-	0.5854	58.54%
CYP2C8 inhibition	+	0.7559	75.59%
CYP inhibitory promiscuity	-	0.6266	62.66%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9100	91.00%
Carcinogenicity (trinary)	Non-required	0.6660	66.60%
Eye corrosion	-	0.9829	98.29%
Eye irritation	-	0.9650	96.50%
Skin irritation	-	0.7347	73.47%
Skin corrosion	-	0.9012	90.12%
Ames mutagenesis	-	0.5600	56.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.9011	90.11%
Micronuclear	+	0.7400	74.00%
Hepatotoxicity	+	0.5305	53.05%
skin sensitisation	-	0.8294	82.94%
Respiratory toxicity	+	0.8000	80.00%
Reproductive toxicity	+	0.9556	95.56%
Mitochondrial toxicity	+	0.9250	92.50%
Nephrotoxicity	-	0.7541	75.41%
Acute Oral Toxicity (c)	III	0.5943	59.43%
Estrogen receptor binding	+	0.8158	81.58%
Androgen receptor binding	+	0.7233	72.33%
Thyroid receptor binding	+	0.5447	54.47%
Glucocorticoid receptor binding	-	0.5187	51.87%
Aromatase binding	+	0.6446	64.46%
PPAR gamma	+	0.6543	65.43%
Honey bee toxicity	-	0.7641	76.41%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	+	0.5500	55.00%
Fish aquatic toxicity	-	0.5000	50.00%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5697	Q9GZT9	Egl nine homolog 1	94.23%	93.40%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	93.91%	91.11%
CHEMBL3310	Q96DB2	Histone deacetylase 11	93.71%	88.56%
CHEMBL3137262	O60341	LSD1/CoREST complex	93.07%	97.09%
CHEMBL216	P11229	Muscarinic acetylcholine receptor M1	91.95%	94.23%
CHEMBL253	P34972	Cannabinoid CB2 receptor	91.89%	97.25%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	91.30%	94.45%
CHEMBL3192	Q9BY41	Histone deacetylase 8	91.11%	93.99%
CHEMBL5608	Q16288	NT-3 growth factor receptor	91.08%	95.89%
CHEMBL238	Q01959	Dopamine transporter	90.41%	95.88%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.80%	95.56%
CHEMBL241	Q14432	Phosphodiesterase 3A	87.79%	92.94%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	86.52%	93.04%
CHEMBL1806	P11388	DNA topoisomerase II alpha	86.35%	89.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	86.15%	96.09%
CHEMBL1937	Q92769	Histone deacetylase 2	86.03%	94.75%
CHEMBL2095226	P05556	Integrin alpha-5/beta-1	85.84%	96.39%
CHEMBL2096618	P11274	Bcr/Abl fusion protein	85.58%	85.83%
CHEMBL3155	P34969	Serotonin 7 (5-HT7) receptor	84.94%	90.71%
CHEMBL230	P35354	Cyclooxygenase-2	84.92%	89.63%
CHEMBL233	P35372	Mu opioid receptor	84.92%	97.93%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	84.90%	99.23%
CHEMBL4302	P08183	P-glycoprotein 1	84.48%	92.98%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	84.09%	92.62%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	83.88%	94.62%
CHEMBL2693	Q9UIQ6	Cystinyl aminopeptidase	82.81%	97.64%
CHEMBL3746	P80365	11-beta-hydroxysteroid dehydrogenase 2	82.27%	94.78%
CHEMBL5646	Q6L5J4	FML2_HUMAN	82.16%	100.00%
CHEMBL1821	P08173	Muscarinic acetylcholine receptor M4	82.00%	94.08%
CHEMBL5028	O14672	ADAM10	81.97%	97.50%
CHEMBL5103	Q969S8	Histone deacetylase 10	81.46%	90.08%
CHEMBL3384	Q16512	Protein kinase N1	80.94%	80.71%
CHEMBL1994	P08235	Mineralocorticoid receptor	80.82%	100.00%
CHEMBL3430907	Q96GD4	Aurora kinase B/Inner centromere protein	80.33%	97.50%
CHEMBL4227	P25090	Lipoxin A4 receptor	80.16%	100.00%
CHEMBL333	P08253	Matrix metalloproteinase-2	80.11%	96.31%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 162960475
• LOTUS: LTS0268237
• wikiData: Q105182404