Carbamic acid (4E,10E)-(8S,9S,12S,13R,14S,16R)-13,19-dihydroxy-8,14-dimethoxy-4,10,12,16-tetramethyl-3-oxo-2-aza-bicyclo[16.3.1]docosa-1(22),4,10,18,20-pentaen-9-yl ester

Details

• Internal ID: 73bc62ac-ed57-4e58-bcf8-ab9dd5aa832c
• Taxonomy: Phenylpropanoids and polyketides > Macrolactams
• IUPAC Name: [(4E,8S,9S,10E,12S,13R,14S,16R)-13,19-dihydroxy-8,14-dimethoxy-4,10,12,16-tetramethyl-3-oxo-2-azabicyclo[16.3.1]docosa-1(22),4,10,18,20-pentaen-9-yl] carbamate
• SMILES (Canonical): CC1CC(C(C(C=C(C(C(CCC=C(C(=O)NC2=CC(=C(C=C2)O)C1)C)OC)OC(=O)N)C)C)O)OC
• SMILES (Isomeric): C[C@H]1C[C@@H]([C@@H]([C@H](/C=C(/[C@@H]([C@H](CC/C=C(/C(=O)NC2=CC(=C(C=C2)O)C1)\C)OC)OC(=O)N)\C)C)O)OC
• InChI: InChI=1S/C28H42N2O7/c1-16-12-20-15-21(10-11-22(20)31)30-27(33)17(2)8-7-9-23(35-5)26(37-28(29)34)19(4)14-18(3)25(32)24(13-16)36-6/h8,10-11,14-16,18,23-26,31-32H,7,9,12-13H2,1-6H3,(H2,29,34)(H,30,33)/b17-8+,19-14+/t16-,18+,23+,24+,25-,26+/m1/s1
• InChI Key: SIXVFZKPBRDLQR-LRFOCFGISA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₈H₄₂N₂O₇
• Molecular Weight: 518.60 g/mol
• Exact Mass: 518.29920168 g/mol
• Topological Polar Surface Area (TPSA): 140.00 Ų
• XlogP: 3.20
• Atomic LogP (AlogP): 4.08
• H-Bond Acceptor: 7
• H-Bond Donor: 4
• Rotatable Bonds: 3

Synonyms

• SCHEMBL12962840
• BDBM50276167
• Carbamic acid (4E,10E)-(8S,9S,12S,13R,14S,16R)-13,19-dihydroxy-8,14-dimethoxy-4,10,12,16-tetramethyl-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	+	0.9460	94.60%
Caco-2	-	0.7451	74.51%
Blood Brain Barrier	+	0.6000	60.00%
Human oral bioavailability	-	0.6000	60.00%
Subcellular localzation	Mitochondria	0.5626	56.26%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9188	91.88%
OATP1B3 inhibitior	+	0.9233	92.33%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.9072	90.72%
BSEP inhibitior	+	0.8215	82.15%
P-glycoprotein inhibitior	+	0.8352	83.52%
P-glycoprotein substrate	+	0.8110	81.10%
CYP3A4 substrate	+	0.6913	69.13%
CYP2C9 substrate	+	0.6262	62.62%
CYP2D6 substrate	-	0.8624	86.24%
CYP3A4 inhibition	-	0.7828	78.28%
CYP2C9 inhibition	-	0.6995	69.95%
CYP2C19 inhibition	-	0.6989	69.89%
CYP2D6 inhibition	-	0.8781	87.81%
CYP1A2 inhibition	-	0.6321	63.21%
CYP2C8 inhibition	+	0.6729	67.29%
CYP inhibitory promiscuity	-	0.9475	94.75%
UGT catelyzed	+	0.6362	63.62%
Carcinogenicity (binary)	-	0.9000	90.00%
Carcinogenicity (trinary)	Non-required	0.5828	58.28%
Eye corrosion	-	0.9881	98.81%
Eye irritation	-	0.9499	94.99%
Skin irritation	-	0.7838	78.38%
Skin corrosion	-	0.9388	93.88%
Ames mutagenesis	+	0.5100	51.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6274	62.74%
Micronuclear	+	0.6900	69.00%
Hepatotoxicity	-	0.5664	56.64%
skin sensitisation	-	0.8704	87.04%
Respiratory toxicity	+	0.7667	76.67%
Reproductive toxicity	+	0.8778	87.78%
Mitochondrial toxicity	+	0.6500	65.00%
Nephrotoxicity	-	0.7864	78.64%
Acute Oral Toxicity (c)	III	0.5924	59.24%
Estrogen receptor binding	+	0.7578	75.78%
Androgen receptor binding	+	0.8194	81.94%
Thyroid receptor binding	+	0.6291	62.91%
Glucocorticoid receptor binding	+	0.8431	84.31%
Aromatase binding	+	0.5638	56.38%
PPAR gamma	+	0.6893	68.93%
Honey bee toxicity	-	0.7669	76.69%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.5700	57.00%
Fish aquatic toxicity	+	0.9497	94.97%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	0.8 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	99.62%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.85%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	97.69%	94.45%
CHEMBL3137262	O60341	LSD1/CoREST complex	96.32%	97.09%
CHEMBL5469	Q14289	Protein tyrosine kinase 2 beta	95.81%	91.03%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	94.98%	95.56%
CHEMBL241	Q14432	Phosphodiesterase 3A	94.67%	92.94%
CHEMBL5608	Q16288	NT-3 growth factor receptor	94.25%	95.89%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	92.25%	93.03%
CHEMBL2581	P07339	Cathepsin D	92.02%	98.95%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.96%	86.33%
CHEMBL213	P08588	Beta-1 adrenergic receptor	90.28%	95.56%
CHEMBL245	P20309	Muscarinic acetylcholine receptor M3	88.49%	97.53%
CHEMBL2535	P11166	Glucose transporter	87.75%	98.75%
CHEMBL3830	Q2M2I8	Adaptor-associated kinase	87.57%	83.10%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	87.47%	85.14%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	87.40%	96.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	87.07%	89.00%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	87.05%	94.00%
CHEMBL1994	P08235	Mineralocorticoid receptor	86.97%	100.00%
CHEMBL340	P08684	Cytochrome P450 3A4	86.89%	91.19%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	85.98%	91.07%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	85.55%	90.71%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	84.49%	96.77%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	84.12%	99.15%
CHEMBL4581	P52732	Kinesin-like protein 1	82.88%	93.18%
CHEMBL3788	O00444	Serine/threonine-protein kinase PLK4	82.78%	83.65%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	82.19%	97.21%
CHEMBL2553	Q15418	Ribosomal protein S6 kinase alpha 1	82.11%	85.11%
CHEMBL217	P14416	Dopamine D2 receptor	80.32%	95.62%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	80.10%	95.89%

Plants that contains it

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Cross-Links

• PubChem: 24984995
• LOTUS: LTS0109902
• wikiData: Q105254116