Burkholdines 1213

Details

• Internal ID: 85594ca9-4cac-4370-a49f-c13276bae785
• Taxonomy: Organic acids and derivatives > Peptidomimetics > Hybrid peptides
• IUPAC Name: 2-[(3S,6S,9S,15R,18R,21R,25R)-3,15-bis(2-amino-2-oxoethyl)-25-[(2R,3R,4S)-2,3-dihydroxy-4-[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxypentadecyl]-18-[(R)-hydroxy-(4-hydroxyphenyl)methyl]-6,21-bis(hydroxymethyl)-2,5,8,11,14,17,20,23-octaoxo-1,4,7,10,13,16,19,22-octazacyclopentacos-9-yl]acetamide
• SMILES (Canonical): CCCCCCCCCCCC(C(C(CC1CC(=O)NC(C(=O)NC(C(=O)NC(C(=O)NCC(=O)NC(C(=O)NC(C(=O)NC(C(=O)N1)CC(=O)N)CO)CC(=O)N)CC(=O)N)C(C2=CC=C(C=C2)O)O)CO)O)O)OC3C(C(C(CO3)O)O)O
• SMILES (Isomeric): CCCCCCCCCCC[C@@H]([C@@H]([C@@H](C[C@@H]1CC(=O)N[C@@H](C(=O)N[C@@H](C(=O)N[C@@H](C(=O)NCC(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N1)CC(=O)N)CO)CC(=O)N)CC(=O)N)[C@@H](C2=CC=C(C=C2)O)O)CO)O)O)O[C@H]3[C@@H]([C@H]([C@@H](CO3)O)O)O
• InChI: InChI=1S/C52H83N11O22/c1-2-3-4-5-6-7-8-9-10-11-35(85-52-45(77)44(76)34(68)24-84-52)43(75)33(67)16-26-17-39(72)59-31(22-64)50(82)63-41(42(74)25-12-14-27(66)15-13-25)51(83)61-28(18-36(53)69)46(78)56-21-40(73)58-29(19-37(54)70)48(80)62-32(23-65)49(81)60-30(20-38(55)71)47(79)57-26/h12-15,26,28-35,41-45,52,64-68,74-77H,2-11,16-24H2,1H3,(H2,53,69)(H2,54,70)(H2,55,71)(H,56,78)(H,57,79)(H,58,73)(H,59,72)(H,60,81)(H,61,83)(H,62,80)(H,63,82)/t26-,28-,29+,30+,31-,32+,33-,34-,35+,41-,42-,43-,44+,45-,52+/m1/s1
• InChI Key: IRPZALKPQWMSQP-DDAPKMJSSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₅₂H₈₃N₁₁O₂₂
• Molecular Weight: 1214.30 g/mol
• Exact Mass: 1213.57141332 g/mol
• Topological Polar Surface Area (TPSA): 563.00 Ų
• XlogP: -5.20
• Atomic LogP (AlogP): -8.19
• H-Bond Acceptor: 22
• H-Bond Donor: 20
• Rotatable Bonds: 26

Synonyms

• CHEMBL2146950

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.5271	52.71%
Caco-2	-	0.8599	85.99%
Blood Brain Barrier	-	0.8000	80.00%
Human oral bioavailability	-	0.7571	75.71%
Subcellular localzation	Mitochondria	0.4723	47.23%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8343	83.43%
OATP1B3 inhibitior	+	0.9278	92.78%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	+	0.9094	90.94%
P-glycoprotein inhibitior	+	0.7415	74.15%
P-glycoprotein substrate	+	0.8825	88.25%
CYP3A4 substrate	+	0.7127	71.27%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8581	85.81%
CYP3A4 inhibition	-	0.7733	77.33%
CYP2C9 inhibition	-	0.9188	91.88%
CYP2C19 inhibition	-	0.8641	86.41%
CYP2D6 inhibition	-	0.8090	80.90%
CYP1A2 inhibition	-	0.8794	87.94%
CYP2C8 inhibition	+	0.7498	74.98%
CYP inhibitory promiscuity	-	0.9232	92.32%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.8800	88.00%
Carcinogenicity (trinary)	Non-required	0.6423	64.23%
Eye corrosion	-	0.9899	98.99%
Eye irritation	-	0.8963	89.63%
Skin irritation	-	0.7740	77.40%
Skin corrosion	-	0.9402	94.02%
Ames mutagenesis	-	0.5886	58.86%
Human Ether-a-go-go-Related Gene inhibition	+	0.7119	71.19%
Micronuclear	+	0.8000	80.00%
Hepatotoxicity	+	0.5522	55.22%
skin sensitisation	-	0.8743	87.43%
Respiratory toxicity	+	0.7000	70.00%
Reproductive toxicity	+	0.9111	91.11%
Mitochondrial toxicity	+	0.8875	88.75%
Nephrotoxicity	-	0.6725	67.25%
Acute Oral Toxicity (c)	III	0.7028	70.28%
Estrogen receptor binding	+	0.7082	70.82%
Androgen receptor binding	+	0.6923	69.23%
Thyroid receptor binding	+	0.5258	52.58%
Glucocorticoid receptor binding	+	0.5992	59.92%
Aromatase binding	+	0.6583	65.83%
PPAR gamma	+	0.7013	70.13%
Honey bee toxicity	-	0.7592	75.92%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	+	0.5388	53.88%
Fish aquatic toxicity	-	0.3747	37.47%

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	99.94%	83.82%
CHEMBL2581	P07339	Cathepsin D	99.50%	98.95%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	99.48%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	99.22%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	97.53%	94.45%
CHEMBL3137262	O60341	LSD1/CoREST complex	96.02%	97.09%
CHEMBL3060	Q9Y345	Glycine transporter 2	94.64%	99.17%
CHEMBL2996	Q05655	Protein kinase C delta	94.33%	97.79%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	93.19%	90.71%
CHEMBL5103	Q969S8	Histone deacetylase 10	92.38%	90.08%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	92.16%	100.00%
CHEMBL253	P34972	Cannabinoid CB2 receptor	91.85%	97.25%
CHEMBL241	Q14432	Phosphodiesterase 3A	89.89%	92.94%
CHEMBL3392948	Q9NP59	Solute carrier family 40 member 1	89.36%	95.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	89.18%	89.00%
CHEMBL226	P30542	Adenosine A1 receptor	88.43%	95.93%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.79%	95.56%
CHEMBL5608	Q16288	NT-3 growth factor receptor	87.24%	95.89%
CHEMBL299	P17252	Protein kinase C alpha	86.88%	98.03%
CHEMBL3892	Q99500	Sphingosine 1-phosphate receptor Edg-3	86.71%	97.29%
CHEMBL5043	Q6P179	Endoplasmic reticulum aminopeptidase 2	86.20%	91.81%
CHEMBL2693	Q9UIQ6	Cystinyl aminopeptidase	85.39%	97.64%
CHEMBL2563	Q9UQL6	Histone deacetylase 5	84.20%	89.67%
CHEMBL1293249	Q13887	Kruppel-like factor 5	84.18%	86.33%
CHEMBL3359	P21462	Formyl peptide receptor 1	83.14%	93.56%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	82.71%	96.90%
CHEMBL3401	O75469	Pregnane X receptor	82.58%	94.73%
CHEMBL2535	P11166	Glucose transporter	81.82%	98.75%
CHEMBL255	P29275	Adenosine A2b receptor	80.97%	98.59%
CHEMBL4227	P25090	Lipoxin A4 receptor	80.53%	100.00%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	80.11%	95.50%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 71460075
• LOTUS: LTS0268033
• wikiData: Q105119021