Pentanamide, 2-(dimethylamino)-3-methyl-N-[3-(1-methylethyl)-7-(2-methylpropyl)-5,8-dioxo-2-oxa-6,9-diazabicyclo[10.2.2]hexadeca-10,12,14,15-tetraen-4-yl]-, [3R-[3R*,4S*(2S*,3S*),7S*]]-

Details

• Internal ID: cee29150-8d35-49d5-ba67-4f5828486aa1
• Taxonomy: Organic acids and derivatives > Carboxylic acids and derivatives > Amino acids, peptides, and analogues > Peptides > Oligopeptides
• IUPAC Name: 2-(dimethylamino)-3-methyl-N-[(10E)-7-(2-methylpropyl)-5,8-dioxo-3-propan-2-yl-2-oxa-6,9-diazabicyclo[10.2.2]hexadeca-1(14),10,12,15-tetraen-4-yl]pentanamide
• SMILES (Canonical): CCC(C)C(C(=O)NC1C(OC2=CC=C(C=C2)C=CNC(=O)C(NC1=O)CC(C)C)C(C)C)N(C)C
• SMILES (Isomeric): CCC(C)C(C(=O)NC1C(OC2=CC=C(C=C2)/C=C/NC(=O)C(NC1=O)CC(C)C)C(C)C)N(C)C
• InChI: InChI=1S/C28H44N4O4/c1-9-19(6)24(32(7)8)28(35)31-23-25(18(4)5)36-21-12-10-20(11-13-21)14-15-29-26(33)22(16-17(2)3)30-27(23)34/h10-15,17-19,22-25H,9,16H2,1-8H3,(H,29,33)(H,30,34)(H,31,35)/b15-14+
• InChI Key: ULQXKOIGVXLOOC-CCEZHUSRSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₈H₄₄N₄O₄
• Molecular Weight: 500.70 g/mol
• Exact Mass: 500.33625590 g/mol
• Topological Polar Surface Area (TPSA): 99.80 Ų
• XlogP: 5.00
• Atomic LogP (AlogP): 3.18
• H-Bond Acceptor: 5
• H-Bond Donor: 3
• Rotatable Bonds: 8

Synonyms

• Ceanothamine A
• Daechuine S2
• ULQXKOIGVXLOOC-CCEZHUSRSA-N
• Pentanamide, 2-(dimethylamino)-3-methyl-N-[3-(1-methylethyl)-7-(2-methylpropyl)-5,8-dioxo-2-oxa-6,9-diazabicyclo[10.2.2]hexadeca-10,12,14,15-tetraen-4-yl]-, [3R-[3R*,4S*(2S*,3S*),7S*]]-
• 2-(Dimethylamino)-N-[7-isobutyl-3-isopropyl-5,8-dioxo-2-oxa-6,9-diazabicyclo[10.2.2]hexadeca-1(14),10,12,15-tetraen-4-yl]-3-methylpentanamide #
• L-Leucinamide, N,N-dimethyl-L-isoleucyl-(3S)-3-hydroxy-L-leucyl-N-[2-(4-hydroxyphenyl)ethenyl]-, cyclic (2->3)-ether

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9410	94.10%
Caco-2	-	0.6627	66.27%
Blood Brain Barrier	-	0.7250	72.50%
Human oral bioavailability	-	0.5143	51.43%
Subcellular localzation	Mitochondria	0.4213	42.13%
OATP2B1 inhibitior	-	0.8612	86.12%
OATP1B1 inhibitior	+	0.8633	86.33%
OATP1B3 inhibitior	+	0.9191	91.91%
MATE1 inhibitior	-	0.8600	86.00%
OCT2 inhibitior	-	0.9068	90.68%
BSEP inhibitior	+	0.9450	94.50%
P-glycoprotein inhibitior	+	0.7659	76.59%
P-glycoprotein substrate	+	0.7650	76.50%
CYP3A4 substrate	+	0.6152	61.52%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.7308	73.08%
CYP3A4 inhibition	+	0.6516	65.16%
CYP2C9 inhibition	-	0.8676	86.76%
CYP2C19 inhibition	-	0.8211	82.11%
CYP2D6 inhibition	-	0.8593	85.93%
CYP1A2 inhibition	-	0.7944	79.44%
CYP2C8 inhibition	-	0.7273	72.73%
CYP inhibitory promiscuity	-	0.8682	86.82%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.8400	84.00%
Carcinogenicity (trinary)	Non-required	0.5828	58.28%
Eye corrosion	-	0.9866	98.66%
Eye irritation	-	0.9707	97.07%
Skin irritation	-	0.7813	78.13%
Skin corrosion	-	0.9259	92.59%
Ames mutagenesis	-	0.5300	53.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7381	73.81%
Micronuclear	+	0.8000	80.00%
Hepatotoxicity	+	0.5373	53.73%
skin sensitisation	-	0.8657	86.57%
Respiratory toxicity	+	0.8111	81.11%
Reproductive toxicity	+	0.8778	87.78%
Mitochondrial toxicity	+	0.9000	90.00%
Nephrotoxicity	-	0.5995	59.95%
Acute Oral Toxicity (c)	III	0.6392	63.92%
Estrogen receptor binding	+	0.6641	66.41%
Androgen receptor binding	+	0.6767	67.67%
Thyroid receptor binding	+	0.5210	52.10%
Glucocorticoid receptor binding	+	0.6690	66.90%
Aromatase binding	+	0.5750	57.50%
PPAR gamma	+	0.7237	72.37%
Honey bee toxicity	-	0.8353	83.53%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.5500	55.00%
Fish aquatic toxicity	+	0.8575	85.75%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	98.55%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.36%	96.09%
CHEMBL3837	P07711	Cathepsin L	94.98%	96.61%
CHEMBL3060	Q9Y345	Glycine transporter 2	91.22%	99.17%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	87.89%	91.11%
CHEMBL3359	P21462	Formyl peptide receptor 1	87.13%	93.56%
CHEMBL253	P34972	Cannabinoid CB2 receptor	84.87%	97.25%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	83.81%	96.90%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	83.30%	89.34%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	82.83%	94.33%
CHEMBL1907605	P24864	Cyclin-dependent kinase 2/cyclin E1	82.55%	92.88%
CHEMBL3401	O75469	Pregnane X receptor	82.50%	94.73%
CHEMBL1806	P11388	DNA topoisomerase II alpha	82.40%	89.00%
CHEMBL340	P08684	Cytochrome P450 3A4	81.47%	91.19%
CHEMBL5103	Q969S8	Histone deacetylase 10	81.30%	90.08%
CHEMBL221	P23219	Cyclooxygenase-1	81.23%	90.17%
CHEMBL255	P29275	Adenosine A2b receptor	80.94%	98.59%
CHEMBL4227	P25090	Lipoxin A4 receptor	80.53%	100.00%

Plants that contains it

• Ziziphus jujuba

Cross-Links

• PubChem: 5370447
• NPASS: NPC196119