Bacicyclin - Compound Card

Bacicyclin

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Bacicyclin

Structure
Zoomed Structure
  • Family: Monera - Bacillaceae
  • Kingdom: Monera
  • Class: Peptide
    • Subclass: Hexapeptide
Canonical Smiles CC[C@@H]([C@@H]1NC(=O)[C@@H](NC(=O)[C@H](CC(C)C)NC(=O)CNC(=O)[C@H](NC(=O)[C@H](NC1=O)C)Cc1ccccc1)C(C)C)C
InChI InChI=1S/C31H48N6O6/c1-8-19(6)26-31(43)33-20(7)27(39)35-23(15-21-12-10-9-11-13-21)28(40)32-16-24(38)34-22(14-17(2)3)29(41)36-25(18(4)5)30(42)37-26/h9-13,17-20,22-23,25-26H,8,14-16H2,1-7H3,(H,32,40)(H,33,43)(H,34,38)(H,35,39)(H,36,41)(H,37,42)/t19-,20+,22-,23+,25-,26-/m0/s1
InChIKey OBFRQFUQLPRNNO-WLBISBHISA-N
Formula C31H48N6O6
HBA 6
HBD 6
MW 600.76
Rotatable Bonds 7
TPSA 174.6
LogP 0.55
Number Rings 2
Number Aromatic Rings 1
Heavy Atom Count 43
Formal Charge 0
Fraction CSP3 0.61
Exact Mass 600.36
Number of Lipinski Rule Violations 2
# Species Family Kingdom NCBI Taxonomy ID
1 Bacillus sp Bacillaceae Monera 1409

Showing of synonyms

  • Wiese J, Abdelmohsen U.R, et al. (2018). Bacicyclin, a new antibacterial cyclic hexapeptide from Bacillus sp. Strain BC028 isolated from Mytilus edulis. Bioorganic & medicinal chemistry letters, 2018, 28(4), 558-561. [View] [PubMed]
Pubchem: 146684013

No compound-protein relationship available.

Structure

SMILES: c1ccccc1CC(C2=O)NC(=O)CNC(=O)CNC(=O)CNC(=O)CNC(=O)CN2

Level: 1

Mol. Weight: 600.76 g/mol

Structure

SMILES: O=C1CNC(=O)CNC(=O)CNC(=O)CNC(=O)CNC(=O)CN1

Level: 0

Mol. Weight: 600.76 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 600.76 g/mol

Antibacterial

Absorption

Caco-2 (logPapp)
-5.92
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-5.2
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
1.76

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.81
Plasma Protein Binding
75.58
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Non-Inhibitor
CYP 1A2 Inhibitor
Non-Inhibitor
CYP 1A2 Substrate
Non-Substrate
CYP 2C19 Inhibitor
Non-Inhibitor
CYP 2C19 Substrate
Substrate
CYP 2C9 Inhibitor
Non-Inhibitor
CYP 2C9 Substrate
Non-Substrate
CYP 2D6 Inhibitor
Non-Inhibitor
CYP 2D6 Substrate
Non-Substrate
CYP 3A4 Inhibitor
Non-Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
4.71
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-3.02
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.31
Liver Injury II
Toxic
hERG Blockers
Toxic
Daphnia Maga
4.13
Micronucleos
Toxic
NR-AhR
Safe
NR-AR
Safe
NR-AR-LBD
Safe
NR-Aromatase
Safe
NR-ER
Safe
NR-ER-LBD
Safe
NR-GR
Safe
NR-PPAR-gamma
Safe
NR-TR
Safe
T. Pyriformis
-5744.67
Rat (Acute)
4.8
Rat (Chronic Oral)
1.95
Fathead Minnow
15.41
Respiratory Disease
Safe
Skin Sensitisation
Safe
SR-ARE
Toxic
SR-ATAD5
Toxic
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Toxic

General Properties

Boiling Point
495.45
Hydration Free Energy
-2.9
Log(D) at pH=7.4
3.53
Log(P)
1.77
Log S
-3.65
Log(Vapor Pressure)
-8.44
Melting Point
284.4
pKa Acid
8.35
pKa Basic
6.26
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Lactoperoxidase P80025 PERL_BOVIN Bos taurus 3 0.9056
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.8698
Thermolysin P00800 THER_BACTH Bacillus thermoproteolyticus 3 0.8659
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.8569
L-lactate dehydrogenase A chain P04642 LDHA_RAT Rattus norvegicus 3 0.8488
cAMP-dependent protein kinase type I-alpha regulatory subunit P00514 KAP0_BOVIN Bos taurus 3 0.8278
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 3 0.8197
Polyribonucleotide nucleotidyltransferase A7ZS61 PNP_ECO24 Escherichia coli O139:H28 3 0.8134
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 2 0.8054
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.7884
prolyl oligopeptidase Q9X6R4 Q9X6R4_AERCA Aeromonas caviae 3 0.7793
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase P0AF12 MTNN_ECOLI Escherichia coli 3 0.7679
Glutamate receptor 2 P19491 GRIA2_RAT Rattus norvegicus 2 0.7678
Type II methyltransferase M.RsrI P14751 MTR1_RHOSH Cereibacter sphaeroides 3 0.7571
Chymotrypsinogen A P00766 CTRA_BOVIN Bos taurus 3 0.7510
Type II methyltransferase M.RsrI P14751 MTR1_RHOSH Cereibacter sphaeroides 3 0.7454
NADPH-dependent oxidoreductase 2-alkenal reductase Q39172 AER_ARATH Arabidopsis thaliana 2 0.7404
Coagulation factor X P00742 FA10_HUMAN Homo sapiens 3 0.7377
Bifunctional epoxide hydrolase 2 P34913 HYES_HUMAN Homo sapiens 2 0.7375
Sodium-dependent dopamine transporter Q7K4Y6 DAT_DROME Drosophila melanogaster 2 0.7366
Indole-3-glycerol phosphate synthase P9WFX7 TRPC_MYCTU Mycobacterium tuberculosis 2 0.7314
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7309
Carbonic anhydrase 1 P00915 CAH1_HUMAN Homo sapiens 2 0.7295
Plasma membrane ATPase Q42932 Q42932_NICPL Nicotiana plumbaginifolia 2 0.7289
Prolyl tripeptidyl peptidase Q7MUW6 PTP_PORGI Porphyromonas gingivalis 2 0.7241
Dihydrofolate reductase P00378 DYR_CHICK Gallus gallus 2 0.7228
Caffeoyl-CoA O-methyltransferase Q40313 CAMT_MEDSA Medicago sativa 3 0.7226
Carbonic anhydrase 4 Q64444 CAH4_MOUSE Mus musculus 2 0.7214
Flavoredoxin Q72HI0 Q72HI0_THET2 Thermus thermophilus 2 0.7212
Cytidine and deoxycytidylate deaminase zinc-binding region Q82Y41 Q82Y41_NITEU Nitrosomonas europaea 3 0.7210
F420-dependent methylenetetrahydromethanopterin dehydrogenase P94951 MTD_METKA Methanopyrus kandleri 2 0.7202
CCA-adding enzyme O28126 CCA_ARCFU Archaeoglobus fulgidus 2 0.7198
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7196
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7178
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7139
Putative snRNP Sm-like protein Q8ZYG5 Q8ZYG5_PYRAE Pyrobaculum aerophilum 2 0.7112
Proton-gated ion channel Q7NDN8 GLIC_GLOVI Gloeobacter violaceus 2 0.7099
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.7051
prolyl oligopeptidase Q9X6R4 Q9X6R4_AERCA Aeromonas caviae 3 0.7036
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 2 0.7026
ABC-type polar amino acid transport system, ATPase component Q8RCC2 Q8RCC2_CALS4 Caldanaerobacter subterraneus subsp. tengcongensis 2 0.7018
S-adenosylmethionine decarboxylase proenzyme P17707 DCAM_HUMAN Homo sapiens 3 0.7004

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