O-methylandrocymbine

Details

• Internal ID: 424f09c3-1ab5-49ee-b314-7b6c7f78602d
• Taxonomy: Alkaloids and derivatives > Androcymbine alkaloids
• IUPAC Name: (1R,10S)-3,4,5,14-tetramethoxy-18-methyl-18-azatetracyclo[8.5.3.01,11.02,7]octadeca-2,4,6,11,14-pentaen-13-one
• SMILES (Canonical): CN1CCC23C=C(C(=O)C=C2C1CCC4=CC(=C(C(=C34)OC)OC)OC)OC
• SMILES (Isomeric): CN1CC[C@@]23C=C(C(=O)C=C2[C@@H]1CCC4=CC(=C(C(=C34)OC)OC)OC)OC
• InChI: InChI=1S/C22H27NO5/c1-23-9-8-22-12-18(26-3)16(24)11-14(22)15(23)7-6-13-10-17(25-2)20(27-4)21(28-5)19(13)22/h10-12,15H,6-9H2,1-5H3/t15-,22+/m0/s1
• InChI Key: AYPIIWGCGUQVNZ-OYHNWAKOSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₂H₂₇NO₅
• Molecular Weight: 385.50 g/mol
• Exact Mass: 385.18892296 g/mol
• Topological Polar Surface Area (TPSA): 57.20 Ų
• XlogP: 2.60
• Atomic LogP (AlogP): 2.64
• H-Bond Acceptor: 6
• H-Bond Donor: 0
• Rotatable Bonds: 4

Synonyms

• CHEBI:80674
• CHEMBL2032098
• Q27149716
• (1R,10S)-3,4,5,14-tetramethoxy-18-methyl-18-azatetracyclo[8.5.3.01,11.02,7]octadeca-2,4,6,11,14-pentaen-13-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9821	98.21%
Caco-2	+	0.9039	90.39%
Blood Brain Barrier	+	0.9000	90.00%
Human oral bioavailability	+	0.5143	51.43%
Subcellular localzation	Mitochondria	0.5404	54.04%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9390	93.90%
OATP1B3 inhibitior	+	0.9493	94.93%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.5750	57.50%
BSEP inhibitior	+	0.8267	82.67%
P-glycoprotein inhibitior	-	0.6201	62.01%
P-glycoprotein substrate	+	0.6201	62.01%
CYP3A4 substrate	+	0.6625	66.25%
CYP2C9 substrate	-	0.8075	80.75%
CYP2D6 substrate	+	0.3717	37.17%
CYP3A4 inhibition	-	0.8667	86.67%
CYP2C9 inhibition	-	0.8806	88.06%
CYP2C19 inhibition	-	0.9243	92.43%
CYP2D6 inhibition	+	0.5098	50.98%
CYP1A2 inhibition	-	0.7405	74.05%
CYP2C8 inhibition	-	0.6373	63.73%
CYP inhibitory promiscuity	-	0.9128	91.28%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Non-required	0.6276	62.76%
Eye corrosion	-	0.9887	98.87%
Eye irritation	-	0.9272	92.72%
Skin irritation	-	0.7624	76.24%
Skin corrosion	-	0.9335	93.35%
Ames mutagenesis	-	0.6400	64.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6746	67.46%
Micronuclear	-	0.6300	63.00%
Hepatotoxicity	-	0.5250	52.50%
skin sensitisation	-	0.8399	83.99%
Respiratory toxicity	+	0.7000	70.00%
Reproductive toxicity	+	0.9222	92.22%
Mitochondrial toxicity	+	0.8250	82.50%
Nephrotoxicity	-	0.6396	63.96%
Acute Oral Toxicity (c)	III	0.6275	62.75%
Estrogen receptor binding	+	0.7933	79.33%
Androgen receptor binding	+	0.6052	60.52%
Thyroid receptor binding	+	0.7052	70.52%
Glucocorticoid receptor binding	+	0.8178	81.78%
Aromatase binding	-	0.4931	49.31%
PPAR gamma	+	0.6020	60.20%
Honey bee toxicity	-	0.6910	69.10%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	+	0.6000	60.00%
Fish aquatic toxicity	+	0.9709	97.09%

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	98.78%	96.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	95.84%	95.56%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	95.71%	96.77%
CHEMBL3192	Q9BY41	Histone deacetylase 8	95.46%	93.99%
CHEMBL253	P34972	Cannabinoid CB2 receptor	94.85%	97.25%
CHEMBL5469	Q14289	Protein tyrosine kinase 2 beta	94.80%	91.03%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	94.78%	93.40%
CHEMBL5203	P33316	dUTP pyrophosphatase	92.47%	99.18%
CHEMBL5608	Q16288	NT-3 growth factor receptor	91.60%	95.89%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	90.27%	85.14%
CHEMBL4247	Q9UM73	ALK tyrosine kinase receptor	90.22%	96.86%
CHEMBL2535	P11166	Glucose transporter	89.46%	98.75%
CHEMBL1293249	Q13887	Kruppel-like factor 5	89.08%	86.33%
CHEMBL217	P14416	Dopamine D2 receptor	88.32%	95.62%
CHEMBL2581	P07339	Cathepsin D	87.29%	98.95%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	86.58%	95.89%
CHEMBL2781	P19634	Sodium/hydrogen exchanger 1	86.47%	90.24%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	86.13%	90.71%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	85.63%	94.00%
CHEMBL4208	P20618	Proteasome component C5	85.39%	90.00%
CHEMBL1871	P10275	Androgen Receptor	85.28%	96.43%
CHEMBL4829	O00763	Acetyl-CoA carboxylase 2	85.14%	98.00%
CHEMBL3820	P35557	Hexokinase type IV	84.79%	91.96%
CHEMBL3746	P80365	11-beta-hydroxysteroid dehydrogenase 2	84.77%	94.78%
CHEMBL2146302	O94925	Glutaminase kidney isoform, mitochondrial	84.42%	100.00%
CHEMBL1902	P62942	FK506-binding protein 1A	84.27%	97.05%
CHEMBL5925	P22413	Ectonucleotide pyrophosphatase/phosphodiesterase family member 1	84.16%	92.38%
CHEMBL5747	Q92793	CREB-binding protein	83.72%	95.12%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	83.70%	97.14%
CHEMBL2069156	Q14145	Kelch-like ECH-associated protein 1	83.53%	82.38%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	83.18%	91.07%
CHEMBL1994	P08235	Mineralocorticoid receptor	82.80%	100.00%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	82.46%	91.11%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	81.63%	93.04%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	81.62%	94.45%
CHEMBL1806	P11388	DNA topoisomerase II alpha	81.37%	89.00%
CHEMBL241	Q14432	Phosphodiesterase 3A	80.69%	92.94%

Plants that contains it

• Colchicum ritchiei
• Colchicum schimperi
• Colchicum szovitsii

Cross-Links

• PubChem: 15286666
• LOTUS: LTS0177684
• wikiData: Q27149716