1',2',3',4'-Tetradehydrotubulosine

Details

• Internal ID: ce982add-d26f-4975-adff-7a1965cf5b63
• Taxonomy: Alkaloids and derivatives > Harmala alkaloids
• IUPAC Name: 1-[[(2R,3R,11bS)-3-ethyl-9,10-dimethoxy-2,3,4,6,7,11b-hexahydro-1H-benzo[a]quinolizin-2-yl]methyl]-9H-pyrido[3,4-b]indol-6-ol
• SMILES (Canonical): CCC1CN2CCC3=CC(=C(C=C3C2CC1CC4=NC=CC5=C4NC6=C5C=C(C=C6)O)OC)OC
• SMILES (Isomeric): CC[C@H]1CN2CCC3=CC(=C(C=C3[C@@H]2C[C@@H]1CC4=NC=CC5=C4NC6=C5C=C(C=C6)O)OC)OC
• InChI: InChI=1S/C29H33N3O3/c1-4-17-16-32-10-8-18-13-27(34-2)28(35-3)15-22(18)26(32)12-19(17)11-25-29-21(7-9-30-25)23-14-20(33)5-6-24(23)31-29/h5-7,9,13-15,17,19,26,31,33H,4,8,10-12,16H2,1-3H3/t17-,19-,26-/m0/s1
• InChI Key: FYIJNEXYFHEJLZ-IAKTWSEQSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₉H₃₃N₃O₃
• Molecular Weight: 471.60 g/mol
• Exact Mass: 471.25219192 g/mol
• Topological Polar Surface Area (TPSA): 70.60 Ų
• XlogP: 5.30
• Atomic LogP (AlogP): 5.63
• H-Bond Acceptor: 5
• H-Bond Donor: 2
• Rotatable Bonds: 5

Synonyms

• CHEMBL481241
• 1-[[(2R,3R,11bS)-3-ethyl-9,10-dimethoxy-2,3,4,6,7,11b-hexahydro-1H-benzo[a]quinolizin-2-yl]methyl]-9H-pyrido[3,4-b]indol-6-ol

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9856	98.56%
Caco-2	-	0.5694	56.94%
Blood Brain Barrier	+	0.7500	75.00%
Human oral bioavailability	-	0.8286	82.86%
Subcellular localzation	Mitochondria	0.6694	66.94%
OATP2B1 inhibitior	-	0.8570	85.70%
OATP1B1 inhibitior	+	0.8860	88.60%
OATP1B3 inhibitior	+	0.9137	91.37%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	+	0.5250	52.50%
BSEP inhibitior	+	0.9932	99.32%
P-glycoprotein inhibitior	+	0.9275	92.75%
P-glycoprotein substrate	+	0.9352	93.52%
CYP3A4 substrate	+	0.6975	69.75%
CYP2C9 substrate	-	0.8000	80.00%
CYP2D6 substrate	+	0.6501	65.01%
CYP3A4 inhibition	-	0.7310	73.10%
CYP2C9 inhibition	-	0.9209	92.09%
CYP2C19 inhibition	-	0.8734	87.34%
CYP2D6 inhibition	+	0.8724	87.24%
CYP1A2 inhibition	-	0.8376	83.76%
CYP2C8 inhibition	+	0.7760	77.60%
CYP inhibitory promiscuity	+	0.5000	50.00%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6757	67.57%
Eye corrosion	-	0.9911	99.11%
Eye irritation	-	0.9653	96.53%
Skin irritation	-	0.7774	77.74%
Skin corrosion	-	0.9425	94.25%
Ames mutagenesis	-	0.6700	67.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8995	89.95%
Micronuclear	+	0.5500	55.00%
Hepatotoxicity	-	0.6000	60.00%
skin sensitisation	-	0.8891	88.91%
Respiratory toxicity	+	0.7778	77.78%
Reproductive toxicity	+	0.9000	90.00%
Mitochondrial toxicity	+	0.9750	97.50%
Nephrotoxicity	-	0.7366	73.66%
Acute Oral Toxicity (c)	III	0.5919	59.19%
Estrogen receptor binding	+	0.8077	80.77%
Androgen receptor binding	+	0.7915	79.15%
Thyroid receptor binding	+	0.7378	73.78%
Glucocorticoid receptor binding	+	0.7578	75.78%
Aromatase binding	+	0.5271	52.71%
PPAR gamma	+	0.5706	57.06%
Honey bee toxicity	-	0.8114	81.14%
Biodegradation	-	0.9500	95.00%
Crustacea aquatic toxicity	+	0.5851	58.51%
Fish aquatic toxicity	+	0.7468	74.68%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	99.69%	96.09%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	99.59%	85.14%
CHEMBL241	Q14432	Phosphodiesterase 3A	98.57%	92.94%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	98.29%	94.45%
CHEMBL5747	Q92793	CREB-binding protein	97.06%	95.12%
CHEMBL3192	Q9BY41	Histone deacetylase 8	96.59%	93.99%
CHEMBL2107	P61073	C-X-C chemokine receptor type 4	95.06%	93.10%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	94.82%	89.62%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	94.71%	91.11%
CHEMBL2041	P07949	Tyrosine-protein kinase receptor RET	94.20%	91.79%
CHEMBL2535	P11166	Glucose transporter	92.71%	98.75%
CHEMBL2581	P07339	Cathepsin D	91.99%	98.95%
CHEMBL3060	Q9Y345	Glycine transporter 2	91.09%	99.17%
CHEMBL1293249	Q13887	Kruppel-like factor 5	91.05%	86.33%
CHEMBL213	P08588	Beta-1 adrenergic receptor	90.34%	95.56%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	90.26%	95.89%
CHEMBL255	P29275	Adenosine A2b receptor	89.51%	98.59%
CHEMBL3137262	O60341	LSD1/CoREST complex	89.28%	97.09%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	88.36%	94.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	88.16%	89.00%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	87.65%	91.71%
CHEMBL1907598	P05106	Integrin alpha-V/beta-3	87.35%	95.71%
CHEMBL5608	Q16288	NT-3 growth factor receptor	85.05%	95.89%
CHEMBL253	P34972	Cannabinoid CB2 receptor	83.48%	97.25%
CHEMBL202	P00374	Dihydrofolate reductase	83.28%	89.92%
CHEMBL5469	Q14289	Protein tyrosine kinase 2 beta	82.27%	91.03%
CHEMBL1951	P21397	Monoamine oxidase A	81.70%	91.49%
CHEMBL1781	P11387	DNA topoisomerase I	81.54%	97.00%
CHEMBL6175	Q9H3R0	Lysine-specific demethylase 4C	81.51%	96.69%
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	81.51%	95.17%
CHEMBL2069156	Q14145	Kelch-like ECH-associated protein 1	81.19%	82.38%
CHEMBL1938212	Q9UPP1	Histone lysine demethylase PHF8	80.78%	98.33%
CHEMBL217	P14416	Dopamine D2 receptor	80.50%	95.62%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	80.38%	95.56%
CHEMBL284	P27487	Dipeptidyl peptidase IV	80.00%	95.69%

Plants that contains it

• Pogonopus speciosus

Cross-Links

• PubChem: 21668793
• LOTUS: LTS0233927
• wikiData: Q105004499