Alterobactin A

Details

• Internal ID: b43ae154-f0fa-4e5c-bb3d-0c8f8af7eef8
• Taxonomy: Organic acids and derivatives > Peptidomimetics > Depsipeptides > Cyclic depsipeptides
• IUPAC Name: (2S)-2-[(3R,9S,12R,18S)-18-[[(3S,4R)-4-amino-8-[(2,3-dihydroxybenzoyl)amino]-3-hydroxyoctanoyl]amino]-3-[(R)-carboxy(hydroxy)methyl]-12-[3-(diaminomethylideneamino)propyl]-2,5,8,11,14,17-hexaoxo-1-oxa-4,7,10,13,16-pentazacyclononadec-9-yl]-2-hydroxyacetic acid
• SMILES (Canonical): C1C(C(=O)NCC(=O)NC(C(=O)NC(C(=O)NCC(=O)NC(C(=O)O1)C(C(=O)O)O)C(C(=O)O)O)CCCN=C(N)N)NC(=O)CC(C(CCCCNC(=O)C2=C(C(=CC=C2)O)O)N)O
• SMILES (Isomeric): C1[C@@H](C(=O)NCC(=O)N[C@@H](C(=O)N[C@H](C(=O)NCC(=O)N[C@@H](C(=O)O1)[C@H](C(=O)O)O)[C@@H](C(=O)O)O)CCCN=C(N)N)NC(=O)C[C@@H]([C@@H](CCCCNC(=O)C2=C(C(=CC=C2)O)O)N)O
• InChI: InChI=1S/C36H53N11O18/c37-16(6-1-2-9-40-29(56)15-5-3-8-19(48)26(15)53)20(49)11-21(50)45-18-14-65-35(64)25(28(55)34(62)63)46-23(52)13-43-32(59)24(27(54)33(60)61)47-31(58)17(7-4-10-41-36(38)39)44-22(51)12-42-30(18)57/h3,5,8,16-18,20,24-25,27-28,48-49,53-55H,1-2,4,6-7,9-14,37H2,(H,40,56)(H,42,57)(H,43,59)(H,44,51)(H,45,50)(H,46,52)(H,47,58)(H,60,61)(H,62,63)(H4,38,39,41)/t16-,17-,18+,20+,24+,25-,27+,28-/m1/s1
• InChI Key: RJOBMSXUHGCZMZ-IBGFIEIMSA-N
• Popularity: 3 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₆H₅₃N₁₁O₁₈
• Molecular Weight: 927.90 g/mol
• Exact Mass: 927.35700388 g/mol
• Topological Polar Surface Area (TPSA): 496.00 Ų
• XlogP: -7.10
• Atomic LogP (AlogP): -8.25
• H-Bond Acceptor: 18
• H-Bond Donor: 17
• Rotatable Bonds: 18

Synonyms

• 153888-52-9

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.5462	54.62%
Caco-2	-	0.8636	86.36%
Blood Brain Barrier	-	0.7500	75.00%
Human oral bioavailability	+	0.5286	52.86%
Subcellular localzation	Nucleus	0.5709	57.09%
OATP2B1 inhibitior	-	0.8605	86.05%
OATP1B1 inhibitior	+	0.8391	83.91%
OATP1B3 inhibitior	+	0.9389	93.89%
MATE1 inhibitior	-	0.8000	80.00%
OCT2 inhibitior	-	0.7250	72.50%
BSEP inhibitior	+	0.7764	77.64%
P-glycoprotein inhibitior	+	0.7402	74.02%
P-glycoprotein substrate	+	0.8929	89.29%
CYP3A4 substrate	+	0.7073	70.73%
CYP2C9 substrate	-	0.8065	80.65%
CYP2D6 substrate	-	0.8252	82.52%
CYP3A4 inhibition	-	0.9435	94.35%
CYP2C9 inhibition	-	0.9416	94.16%
CYP2C19 inhibition	-	0.9101	91.01%
CYP2D6 inhibition	-	0.9216	92.16%
CYP1A2 inhibition	-	0.8495	84.95%
CYP2C8 inhibition	+	0.7024	70.24%
CYP inhibitory promiscuity	-	0.9941	99.41%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.8500	85.00%
Carcinogenicity (trinary)	Non-required	0.6520	65.20%
Eye corrosion	-	0.9872	98.72%
Eye irritation	-	0.8973	89.73%
Skin irritation	-	0.7620	76.20%
Skin corrosion	-	0.9305	93.05%
Ames mutagenesis	-	0.5600	56.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4131	41.31%
Micronuclear	+	0.7700	77.00%
Hepatotoxicity	-	0.5625	56.25%
skin sensitisation	-	0.8308	83.08%
Respiratory toxicity	+	0.7889	78.89%
Reproductive toxicity	+	0.8889	88.89%
Mitochondrial toxicity	+	0.8000	80.00%
Nephrotoxicity	+	0.4553	45.53%
Acute Oral Toxicity (c)	III	0.6079	60.79%
Estrogen receptor binding	+	0.7587	75.87%
Androgen receptor binding	+	0.7342	73.42%
Thyroid receptor binding	+	0.5391	53.91%
Glucocorticoid receptor binding	-	0.5213	52.13%
Aromatase binding	+	0.6666	66.66%
PPAR gamma	+	0.7074	70.74%
Honey bee toxicity	-	0.7669	76.69%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.7900	79.00%
Fish aquatic toxicity	-	0.7943	79.43%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4040	P28482	MAP kinase ERK2	99.93%	83.82%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	99.71%	91.11%
CHEMBL2581	P07339	Cathepsin D	99.44%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.40%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	98.06%	94.45%
CHEMBL3137262	O60341	LSD1/CoREST complex	93.31%	97.09%
CHEMBL2107	P61073	C-X-C chemokine receptor type 4	93.11%	93.10%
CHEMBL3392948	Q9NP59	Solute carrier family 40 member 1	92.07%	95.00%
CHEMBL1907605	P24864	Cyclin-dependent kinase 2/cyclin E1	92.01%	92.88%
CHEMBL2535	P11166	Glucose transporter	90.96%	98.75%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	90.08%	90.71%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	89.31%	99.23%
CHEMBL3060	Q9Y345	Glycine transporter 2	89.28%	99.17%
CHEMBL4296	Q15858	Sodium channel protein type IX alpha subunit	89.22%	96.11%
CHEMBL3401	O75469	Pregnane X receptor	88.87%	94.73%
CHEMBL3830	Q2M2I8	Adaptor-associated kinase	86.93%	83.10%
CHEMBL3891	P07384	Calpain 1	86.60%	93.04%
CHEMBL2096618	P11274	Bcr/Abl fusion protein	86.52%	85.83%
CHEMBL4101	P17612	cAMP-dependent protein kinase alpha-catalytic subunit	85.60%	82.86%
CHEMBL1255126	O15151	Protein Mdm4	85.46%	90.20%
CHEMBL3384	Q16512	Protein kinase N1	85.44%	80.71%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	85.26%	99.15%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	84.89%	91.24%
CHEMBL5103	Q969S8	Histone deacetylase 10	84.89%	90.08%
CHEMBL4227	P25090	Lipoxin A4 receptor	84.46%	100.00%
CHEMBL2563	Q9UQL6	Histone deacetylase 5	84.36%	89.67%
CHEMBL5261	Q7L7X3	Serine/threonine-protein kinase TAO1	83.49%	89.33%
CHEMBL3310	Q96DB2	Histone deacetylase 11	83.30%	88.56%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	83.30%	95.56%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	83.29%	96.38%
CHEMBL220	P22303	Acetylcholinesterase	82.08%	94.45%
CHEMBL2514	O95665	Neurotensin receptor 2	81.27%	100.00%
CHEMBL255	P29275	Adenosine A2b receptor	80.11%	98.59%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 132427651
• LOTUS: LTS0139195
• wikiData: Q105237637