5H-Dibenzo[a,c]cycloheptene-2-carboxylic acid, 5-(acetylamino)-6,7-dihydro-3-hydroxy-9,10,11-trimethoxy-, methyl ester, (S)-

Details

• Internal ID: e6af2793-4663-4086-9b5a-f88c7f37606c
• Taxonomy: Alkaloids and derivatives > Allocolchicine alkaloids
• IUPAC Name: methyl 8-acetamido-5-hydroxy-13,14,15-trimethoxytricyclo[9.4.0.02,7]pentadeca-1(15),2,4,6,11,13-hexaene-4-carboxylate
• InChI: InChI=1S/C22H25NO7/c1-11(24)23-16-7-6-12-8-18(27-2)20(28-3)21(29-4)19(12)14-9-15(22(26)30-5)17(25)10-13(14)16/h8-10,16,25H,6-7H2,1-5H3,(H,23,24)
• InChI Key: VOKPQOKKNBHZIX-UHFFFAOYSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₂H₂₅NO₇
• Molecular Weight: 415.40 g/mol
• Exact Mass: 415.16310214 g/mol
• Topological Polar Surface Area (TPSA): 103.00 Ų
• XlogP: 3.00
• Atomic LogP (AlogP): 3.00
• H-Bond Acceptor: 7
• H-Bond Donor: 2
• Rotatable Bonds: 5

Synonyms

• 5H-Dibenzo[a,c]cycloheptene-2-carboxylic acid, 5-(acetylamino)-6,7-dihydro-3-hydroxy-9,10,11-trimethoxy-, methyl ester, (5S)-
• 5H-Dibenzo[a,c]cycloheptene-2-carboxylic acid, 5-(acetylamino)-6,7-dihydro-3-hydroxy-9,10,11-trimethoxy-, methyl ester, (S)-
• Methyl 5-(acetylamino)-3-hydroxy-9,10,11-trimethoxy-6,7-dihydro-5H-dibenzo[a,c]cycloheptene-2-carboxylate #

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9283	92.83%
Caco-2	+	0.7405	74.05%
Blood Brain Barrier	-	0.5750	57.50%
Human oral bioavailability	+	0.6000	60.00%
Subcellular localzation	Nucleus	0.5157	51.57%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9075	90.75%
OATP1B3 inhibitior	+	0.9264	92.64%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.9072	90.72%
BSEP inhibitior	+	0.9020	90.20%
P-glycoprotein inhibitior	-	0.7452	74.52%
P-glycoprotein substrate	+	0.8271	82.71%
CYP3A4 substrate	+	0.6946	69.46%
CYP2C9 substrate	-	0.8169	81.69%
CYP2D6 substrate	-	0.8403	84.03%
CYP3A4 inhibition	-	0.8912	89.12%
CYP2C9 inhibition	-	0.8756	87.56%
CYP2C19 inhibition	-	0.9407	94.07%
CYP2D6 inhibition	-	0.9367	93.67%
CYP1A2 inhibition	-	0.8872	88.72%
CYP2C8 inhibition	+	0.9252	92.52%
CYP inhibitory promiscuity	-	0.8725	87.25%
UGT catelyzed	-	0.7000	70.00%
Carcinogenicity (binary)	-	0.9300	93.00%
Carcinogenicity (trinary)	Non-required	0.6079	60.79%
Eye corrosion	-	0.9926	99.26%
Eye irritation	-	0.8779	87.79%
Skin irritation	-	0.8022	80.22%
Skin corrosion	-	0.9477	94.77%
Ames mutagenesis	-	0.8300	83.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5661	56.61%
Micronuclear	+	0.7200	72.00%
Hepatotoxicity	-	0.6198	61.98%
skin sensitisation	-	0.9343	93.43%
Respiratory toxicity	+	0.7111	71.11%
Reproductive toxicity	+	0.9111	91.11%
Mitochondrial toxicity	+	0.8250	82.50%
Nephrotoxicity	-	0.5894	58.94%
Acute Oral Toxicity (c)	III	0.5504	55.04%
Estrogen receptor binding	+	0.9049	90.49%
Androgen receptor binding	+	0.6545	65.45%
Thyroid receptor binding	+	0.7709	77.09%
Glucocorticoid receptor binding	+	0.8335	83.35%
Aromatase binding	-	0.5889	58.89%
PPAR gamma	+	0.7710	77.10%
Honey bee toxicity	-	0.8623	86.23%
Biodegradation	-	0.9250	92.50%
Crustacea aquatic toxicity	-	0.6000	60.00%
Fish aquatic toxicity	+	0.9163	91.63%

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	98.33%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.45%	91.11%
CHEMBL2535	P11166	Glucose transporter	94.17%	98.75%
CHEMBL2581	P07339	Cathepsin D	93.03%	98.95%
CHEMBL217	P14416	Dopamine D2 receptor	92.61%	95.62%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	92.43%	85.14%
CHEMBL2041	P07949	Tyrosine-protein kinase receptor RET	91.59%	91.79%
CHEMBL3060	Q9Y345	Glycine transporter 2	90.03%	99.17%
CHEMBL2056	P21728	Dopamine D1 receptor	90.01%	91.00%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	89.52%	93.03%
CHEMBL2413	P32246	C-C chemokine receptor type 1	88.40%	89.50%
CHEMBL241	Q14432	Phosphodiesterase 3A	88.36%	92.94%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	86.71%	95.89%
CHEMBL340	P08684	Cytochrome P450 3A4	86.59%	91.19%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	85.89%	90.71%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	85.11%	92.62%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	83.74%	94.33%
CHEMBL1075317	P61964	WD repeat-containing protein 5	83.74%	96.33%
CHEMBL4208	P20618	Proteasome component C5	83.00%	90.00%
CHEMBL3192	Q9BY41	Histone deacetylase 8	82.49%	93.99%
CHEMBL5608	Q16288	NT-3 growth factor receptor	82.12%	95.89%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	81.00%	99.23%

Plants that contains it

• Colchicum decaisnei

Cross-Links

• PubChem: 634450
• LOTUS: LTS0118309
• wikiData: Q105290235