Serobactin B

Details

• Internal ID: 33e15dac-65cc-4050-b17d-3b6af166e5a1
• Taxonomy: Organic acids and derivatives > Peptidomimetics > Hybrid peptides
• IUPAC Name: 4-[[(2S)-1-[[1-carboxy-1-hydroxy-3-[[(2R,3S)-3-hydroxy-1-[[(2S)-3-hydroxy-1-[[(3S)-1-hydroxy-2-oxopiperidin-3-yl]amino]-1-oxopropan-2-yl]amino]-1-oxobutan-2-yl]amino]-3-oxopropan-2-yl]amino]-3-hydroxy-1-oxopropan-2-yl]amino]-3-(dodecanoylamino)-2-hydroxy-4-oxobutanoic acid
• SMILES (Canonical): CCCCCCCCCCCC(=O)NC(C(C(=O)O)O)C(=O)NC(CO)C(=O)NC(C(C(=O)O)O)C(=O)NC(C(C)O)C(=O)NC(CO)C(=O)NC1CCCN(C1=O)O
• SMILES (Isomeric): CCCCCCCCCCCC(=O)NC(C(C(=O)O)O)C(=O)N[C@@H](CO)C(=O)NC(C(C(=O)O)O)C(=O)N[C@H]([C@H](C)O)C(=O)N[C@@H](CO)C(=O)N[C@H]1CCCN(C1=O)O
• InChI: InChI=1S/C35H59N7O17/c1-3-4-5-6-7-8-9-10-11-14-22(46)39-24(26(47)34(55)56)31(52)38-21(17-44)29(50)41-25(27(48)35(57)58)32(53)40-23(18(2)45)30(51)37-20(16-43)28(49)36-19-13-12-15-42(59)33(19)54/h18-21,23-27,43-45,47-48,59H,3-17H2,1-2H3,(H,36,49)(H,37,51)(H,38,52)(H,39,46)(H,40,53)(H,41,50)(H,55,56)(H,57,58)/t18-,19-,20-,21-,23+,24?,25?,26?,27?/m0/s1
• InChI Key: LQPRYCPJOYXBHP-ZPDUTISPSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₅H₅₉N₇O₁₇
• Molecular Weight: 849.90 g/mol
• Exact Mass: 849.39674344 g/mol
• Topological Polar Surface Area (TPSA): 391.00 Ų
• XlogP: -2.00
• Atomic LogP (AlogP): -4.92
• H-Bond Acceptor: 15
• H-Bond Donor: 14
• Rotatable Bonds: 28

Synonyms

• 4-[[(2S)-1-[[1-carboxy-1-hydroxy-3-[[(2R,3S)-3-hydroxy-1-[[(2S)-3-hydroxy-1-[[(3S)-1-hydroxy-2-oxopiperidin-3-yl]amino]-1-oxopropan-2-yl]amino]-1-oxobutan-2-yl]amino]-3-oxopropan-2-yl]amino]-3-hydroxy-1-oxopropan-2-yl]amino]-3-(dodecanoylamino)-2-hydroxy-4-oxobutanoic acid
• 3-(((2S)-2-((3-carboxy-1,3-dihydroxy-2-((1-hydroxydodecylidene)amino)propylidene)amino)-1,3-dihydroxypropylidene)amino)-2-hydroxy-3-(((1R,2S)-2-hydroxy-1-(((1S)-2-hydroxy-1-(((3S)-1-hydroxy-2-oxopiperidin-3-yl)-C-hydroxycarbonimidoyl)ethyl)-C-hydroxycarbonimidoyl)propyl)-C-hydroxycarbonimidoyl)propanoate
• 3-{[(2S)-2-({3-carboxy-1,3-dihydroxy-2-[(1-hydroxydodecylidene)amino]propylidene}amino)-1,3-dihydroxypropylidene]amino}-2-hydroxy-3-{[(1R,2S)-2-hydroxy-1-{[(1S)-2-hydroxy-1-{[(3S)-1-hydroxy-2-oxopiperidin-3-yl]-C-hydroxycarbonimidoyl}ethyl]-C-hydroxycarbonimidoyl}propyl]-C-hydroxycarbonimidoyl}propanoate
• 4-(((2S)-1-((1-carboxy-1-hydroxy-3-(((2R,3S)-3-hydroxy-1-(((2S)-3-hydroxy-1-(((3S)-1-hydroxy-2-oxopiperidin-3-yl)amino)-1-oxopropan-2-yl)amino)-1-oxobutan-2-yl)amino)-3-oxopropan-2-yl)amino)-3-hydroxy-1-oxopropan-2-yl)amino)-3-(dodecanoylamino)-2-hydroxy-4-oxobutanoic acid
• RefChem:182526
• CHEBI:219869

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.6640	66.40%
Caco-2	-	0.8638	86.38%
Blood Brain Barrier	-	0.8250	82.50%
Human oral bioavailability	-	0.7714	77.14%
Subcellular localzation	Mitochondria	0.6046	60.46%
OATP2B1 inhibitior	-	0.5769	57.69%
OATP1B1 inhibitior	+	0.8772	87.72%
OATP1B3 inhibitior	+	0.9283	92.83%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	+	0.8039	80.39%
P-glycoprotein inhibitior	+	0.7258	72.58%
P-glycoprotein substrate	+	0.6995	69.95%
CYP3A4 substrate	+	0.6285	62.85%
CYP2C9 substrate	-	0.7914	79.14%
CYP2D6 substrate	-	0.8550	85.50%
CYP3A4 inhibition	-	0.9055	90.55%
CYP2C9 inhibition	-	0.8459	84.59%
CYP2C19 inhibition	-	0.8322	83.22%
CYP2D6 inhibition	-	0.8763	87.63%
CYP1A2 inhibition	-	0.8926	89.26%
CYP2C8 inhibition	-	0.7299	72.99%
CYP inhibitory promiscuity	-	0.9783	97.83%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.7400	74.00%
Carcinogenicity (trinary)	Non-required	0.5655	56.55%
Eye corrosion	-	0.9832	98.32%
Eye irritation	-	0.8963	89.63%
Skin irritation	-	0.7625	76.25%
Skin corrosion	-	0.9325	93.25%
Ames mutagenesis	-	0.7400	74.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6530	65.30%
Micronuclear	+	0.7800	78.00%
Hepatotoxicity	-	0.5967	59.67%
skin sensitisation	-	0.8511	85.11%
Respiratory toxicity	+	0.6556	65.56%
Reproductive toxicity	+	0.8111	81.11%
Mitochondrial toxicity	+	0.8750	87.50%
Nephrotoxicity	+	0.6580	65.80%
Acute Oral Toxicity (c)	III	0.6255	62.55%
Estrogen receptor binding	+	0.7666	76.66%
Androgen receptor binding	+	0.5262	52.62%
Thyroid receptor binding	-	0.5000	50.00%
Glucocorticoid receptor binding	-	0.4766	47.66%
Aromatase binding	+	0.6097	60.97%
PPAR gamma	+	0.6686	66.86%
Honey bee toxicity	-	0.9403	94.03%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	+	0.5000	50.00%
Fish aquatic toxicity	-	0.4350	43.50%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	99.84%	98.95%
CHEMBL3060	Q9Y345	Glycine transporter 2	96.35%	99.17%
CHEMBL4040	P28482	MAP kinase ERK2	96.33%	83.82%
CHEMBL3359	P21462	Formyl peptide receptor 1	95.79%	93.56%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.76%	96.09%
CHEMBL1795139	Q8IU80	Transmembrane protease serine 6	95.57%	98.33%
CHEMBL230	P35354	Cyclooxygenase-2	94.05%	89.63%
CHEMBL221	P23219	Cyclooxygenase-1	93.04%	90.17%
CHEMBL4588	P22894	Matrix metalloproteinase 8	92.73%	94.66%
CHEMBL321	P14780	Matrix metalloproteinase 9	92.69%	92.12%
CHEMBL2107	P61073	C-X-C chemokine receptor type 4	92.02%	93.10%
CHEMBL3392948	Q9NP59	Solute carrier family 40 member 1	91.76%	95.00%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	91.62%	90.71%
CHEMBL5043	Q6P179	Endoplasmic reticulum aminopeptidase 2	90.96%	91.81%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	90.73%	93.00%
CHEMBL3837	P07711	Cathepsin L	90.30%	96.61%
CHEMBL259	P32245	Melanocortin receptor 4	89.57%	95.38%
CHEMBL2514	O95665	Neurotensin receptor 2	89.45%	100.00%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	89.44%	96.47%
CHEMBL3468	P55210	Caspase-7	89.18%	95.68%
CHEMBL3892	Q99500	Sphingosine 1-phosphate receptor Edg-3	88.97%	97.29%
CHEMBL5255	O00206	Toll-like receptor 4	88.90%	92.50%
CHEMBL4072	P07858	Cathepsin B	88.81%	93.67%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	88.42%	99.23%
CHEMBL5103	Q969S8	Histone deacetylase 10	88.15%	90.08%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	88.00%	94.45%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	87.60%	96.90%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	87.50%	96.38%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	87.31%	95.50%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	86.68%	97.14%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	86.57%	93.03%
CHEMBL2781	P19634	Sodium/hydrogen exchanger 1	86.55%	90.24%
CHEMBL1907591	P30926	Neuronal acetylcholine receptor; alpha4/beta4	86.33%	100.00%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	86.02%	100.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	85.64%	97.09%
CHEMBL4227	P25090	Lipoxin A4 receptor	85.04%	100.00%
CHEMBL2534	O15530	3-phosphoinositide dependent protein kinase-1	84.75%	95.36%
CHEMBL1944495	P28065	Proteasome subunit beta type-9	84.61%	97.50%
CHEMBL333	P08253	Matrix metalloproteinase-2	84.59%	96.31%
CHEMBL3430907	Q96GD4	Aurora kinase B/Inner centromere protein	82.61%	97.50%
CHEMBL2001	Q9H244	Purinergic receptor P2Y12	82.54%	96.00%
CHEMBL2955	O95136	Sphingosine 1-phosphate receptor Edg-5	82.51%	92.86%
CHEMBL340	P08684	Cytochrome P450 3A4	81.38%	91.19%
CHEMBL3024	P53350	Serine/threonine-protein kinase PLK1	80.93%	97.43%
CHEMBL253	P34972	Cannabinoid CB2 receptor	80.87%	97.25%
CHEMBL1907605	P24864	Cyclin-dependent kinase 2/cyclin E1	80.57%	92.88%
CHEMBL3776	Q14790	Caspase-8	80.33%	97.06%
CHEMBL299	P17252	Protein kinase C alpha	80.30%	98.03%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	80.09%	94.33%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.01%	95.89%

Plants that contains it

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Cross-Links

• PubChem: 139588805
• LOTUS: LTS0271252
• wikiData: Q105155660