Carbamic acid (4E,10E)-(8S,9S,12S,13R,14S,16R)-13,20-dihydroxy-8,14-dimethoxy-10,12,16-trimethyl-3-oxo-2-aza-bicyclo[16.3.1]docosa-1(22),4,10,18,20-pentaen-9-yl ester

Details

• Internal ID: bc65bf22-1d6e-4d8f-b5d8-fcfff0655805
• Taxonomy: Phenylpropanoids and polyketides > Macrolactams
• IUPAC Name: [(4E,8S,9S,10E,12S,13R,14S,16R)-13,20-dihydroxy-8,14-dimethoxy-10,12,16-trimethyl-3-oxo-2-azabicyclo[16.3.1]docosa-1(21),4,10,18(22),19-pentaen-9-yl] carbamate
• InChI: InChI=1S/C27H40N2O7/c1-16-10-19-13-20(15-21(30)14-19)29-24(31)9-7-6-8-22(34-4)26(36-27(28)33)18(3)12-17(2)25(32)23(11-16)35-5/h7,9,12-17,22-23,25-26,30,32H,6,8,10-11H2,1-5H3,(H2,28,33)(H,29,31)/b9-7+,18-12+/t16-,17+,22+,23+,25-,26+/m1/s1
• InChI Key: PSWCTDDGKOXOPF-WPNUPFKDSA-N
• Popularity: 3 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₇H₄₀N₂O₇
• Molecular Weight: 504.60 g/mol
• Exact Mass: 504.28355162 g/mol
• Topological Polar Surface Area (TPSA): 140.00 Ų
• XlogP: 2.80
• Atomic LogP (AlogP): 3.69
• H-Bond Acceptor: 7
• H-Bond Donor: 4
• Rotatable Bonds: 3

Synonyms

• EH21A14
• SCHEMBL14094942
• CHEBI:197588
• BDBM50233854
• [(4E,8S,9S,10E,12S,13R,14S,16R)-13,20-dihydroxy-8,14-dimethoxy-10,12,16-trimethyl-3-oxo-2-azabicyclo[16.3.1]docosa-1(21),4,10,18(22),19-pentaen-9-yl] carbamate
• carbamic acid (4E,10E)-(8S,9S,12S,13R,14S,16R)-13,20-dihydroxy-8,14-dimethoxy-10,12,16-trimethyl-3-oxo-2-aza-bicyclo[16.3.1]docosa-1(21),4,10,18(22),19-pentaen-9-yl ester
• Carbamic acid (4E,10E)-(8S,9S,12S,13R,14S,16R)-13,20-dihydroxy-8,14-dimethoxy-10,12,16-trimethyl-3-oxo-2-aza-bicyclo[16.3.1]docosa-1(22),4,10,18,20-pentaen-9-yl ester

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8788	87.88%
Caco-2	-	0.7050	70.50%
Blood Brain Barrier	+	0.5500	55.00%
Human oral bioavailability	-	0.6571	65.71%
Subcellular localzation	Mitochondria	0.5585	55.85%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8840	88.40%
OATP1B3 inhibitior	+	0.9259	92.59%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.8822	88.22%
BSEP inhibitior	+	0.9152	91.52%
P-glycoprotein inhibitior	+	0.8297	82.97%
P-glycoprotein substrate	+	0.7664	76.64%
CYP3A4 substrate	+	0.7030	70.30%
CYP2C9 substrate	-	0.5966	59.66%
CYP2D6 substrate	-	0.8659	86.59%
CYP3A4 inhibition	-	0.8351	83.51%
CYP2C9 inhibition	-	0.7599	75.99%
CYP2C19 inhibition	-	0.7177	71.77%
CYP2D6 inhibition	-	0.8881	88.81%
CYP1A2 inhibition	-	0.7285	72.85%
CYP2C8 inhibition	+	0.6474	64.74%
CYP inhibitory promiscuity	-	0.9169	91.69%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9200	92.00%
Carcinogenicity (trinary)	Non-required	0.5675	56.75%
Eye corrosion	-	0.9877	98.77%
Eye irritation	-	0.9583	95.83%
Skin irritation	-	0.7834	78.34%
Skin corrosion	-	0.9369	93.69%
Ames mutagenesis	-	0.5500	55.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6025	60.25%
Micronuclear	+	0.7400	74.00%
Hepatotoxicity	-	0.5125	51.25%
skin sensitisation	-	0.8694	86.94%
Respiratory toxicity	+	0.7778	77.78%
Reproductive toxicity	+	0.8333	83.33%
Mitochondrial toxicity	+	0.6750	67.50%
Nephrotoxicity	-	0.6816	68.16%
Acute Oral Toxicity (c)	III	0.6223	62.23%
Estrogen receptor binding	+	0.6987	69.87%
Androgen receptor binding	+	0.7640	76.40%
Thyroid receptor binding	+	0.5542	55.42%
Glucocorticoid receptor binding	+	0.8241	82.41%
Aromatase binding	+	0.5576	55.76%
PPAR gamma	+	0.6766	67.66%
Honey bee toxicity	-	0.7518	75.18%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.5300	53.00%
Fish aquatic toxicity	+	0.9165	91.65%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	16 nM	Kd	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	99.67%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.63%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	97.28%	94.45%
CHEMBL3137262	O60341	LSD1/CoREST complex	95.57%	97.09%
CHEMBL241	Q14432	Phosphodiesterase 3A	95.50%	92.94%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	94.06%	96.21%
CHEMBL2581	P07339	Cathepsin D	91.75%	98.95%
CHEMBL5608	Q16288	NT-3 growth factor receptor	90.71%	95.89%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.70%	95.56%
CHEMBL4208	P20618	Proteasome component C5	89.40%	90.00%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	89.02%	93.03%
CHEMBL1806	P11388	DNA topoisomerase II alpha	87.33%	89.00%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	86.95%	96.95%
CHEMBL245	P20309	Muscarinic acetylcholine receptor M3	86.86%	97.53%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	85.45%	91.07%
CHEMBL215	P09917	Arachidonate 5-lipoxygenase	85.17%	92.68%
CHEMBL1994	P08235	Mineralocorticoid receptor	84.44%	100.00%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	83.01%	94.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	82.85%	86.33%
CHEMBL5469	Q14289	Protein tyrosine kinase 2 beta	82.63%	91.03%
CHEMBL221	P23219	Cyclooxygenase-1	82.52%	90.17%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	82.38%	99.23%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	82.26%	85.14%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	82.11%	90.71%
CHEMBL340	P08684	Cytochrome P450 3A4	81.99%	91.19%
CHEMBL3713062	P10646	Tissue factor pathway inhibitor	81.85%	97.33%
CHEMBL2553	Q15418	Ribosomal protein S6 kinase alpha 1	81.38%	85.11%
CHEMBL5852	Q96P65	Pyroglutamylated RFamide peptide receptor	81.37%	85.00%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	80.49%	97.21%
CHEMBL3437	Q16853	Amine oxidase, copper containing	80.43%	94.00%
CHEMBL3830	Q2M2I8	Adaptor-associated kinase	80.30%	83.10%
CHEMBL211	P08172	Muscarinic acetylcholine receptor M2	80.21%	94.97%

Plants that contains it

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Cross-Links

• PubChem: 44446535
• LOTUS: LTS0065010
• wikiData: Q104995832