Cyclotheonamide A

Identification

Name
Cyclotheonamide A
Accession Number
DB04269  (EXPT01047)
Type
Small Molecule
Groups
Experimental
Description

Cyclotheonamide A is a cyclic peptide isolated from the marine sponge Theonella.

Structure
Thumb
Synonyms
Not Available
External IDs
MS-1144
Categories
UNII
2Y1TEH8EW7
CAS number
129033-04-1
Weight
Average: 731.798
Monoisotopic: 731.339109461
Chemical Formula
C36H45N9O8
InChI Key
CDWXSPKJKIUEQF-BIXWYCRZSA-N
InChI
InChI=1S/C36H45N9O8/c37-36(38)39-16-4-8-26-31(49)34(52)44-27(19-22-6-2-1-3-7-22)32(50)42-24(18-23-10-13-25(47)14-11-23)12-15-30(48)40-20-28(41-21-46)35(53)45-17-5-9-29(45)33(51)43-26/h1-3,6-7,10-15,21,24,26-29,47H,4-5,8-9,16-20H2,(H,40,48)(H,41,46)(H,42,50)(H,43,51)(H,44,52)(H4,37,38,39)/b15-12+/t24-,26+,27-,28+,29+/m1/s1
IUPAC Name
N-[(3S,7R,10S,16S,21aS)-7-benzyl-3-(3-carbamimidamidopropyl)-10-[(4-hydroxyphenyl)methyl]-1,4,5,8,13,17-hexaoxo-1H,2H,3H,4H,5H,6H,7H,8H,9H,10H,13H,14H,15H,16H,17H,19H,20H,21H,21aH-pyrrolo[2,1-j]1,4,8,11,15-pentaazacyclononadecan-16-yl]formamide
SMILES
[H][C@@]12CCCN1C(=O)[C@H](CNC(=O)\C=C\[C@H](CC1=CC=C(O)C=C1)NC(=O)[C@@H](CC1=CC=CC=C1)NC(=O)C(=O)[C@H](CCCNC(N)=N)NC2=O)NC=O

Pharmacology

Indication
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UTrypsin-1Not AvailableHumans
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Not Available
Food Interactions
Not Available

References

General References
Not Available
External Links
PubChem Compound
5287991
PubChem Substance
46507851
ChemSpider
4450240
BindingDB
50118723
ChEMBL
CHEMBL342672
ZINC
ZINC000027439086
PDBe Ligand
CTA
PDB Entries
1tyn

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.0453 mg/mLALOGPS
logP-0.36ALOGPS
logP-1.4ChemAxon
logS-4.2ALOGPS
pKa (Strongest Acidic)9.5ChemAxon
pKa (Strongest Basic)11.94ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count11ChemAxon
Hydrogen Donor Count9ChemAxon
Polar Surface Area265.01 Å2ChemAxon
Rotatable Bond Count9ChemAxon
Refractivity202.64 m3·mol-1ChemAxon
Polarizability73.17 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.7332
Blood Brain Barrier-0.9377
Caco-2 permeable-0.792
P-glycoprotein substrateSubstrate0.822
P-glycoprotein inhibitor INon-inhibitor0.8526
P-glycoprotein inhibitor IINon-inhibitor0.7345
Renal organic cation transporterNon-inhibitor0.654
CYP450 2C9 substrateNon-substrate0.7419
CYP450 2D6 substrateNon-substrate0.7914
CYP450 3A4 substrateNon-substrate0.5279
CYP450 1A2 substrateNon-inhibitor0.8906
CYP450 2C9 inhibitorNon-inhibitor0.8628
CYP450 2D6 inhibitorNon-inhibitor0.8768
CYP450 2C19 inhibitorNon-inhibitor0.8617
CYP450 3A4 inhibitorNon-inhibitor0.8783
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9683
Ames testNon AMES toxic0.5989
CarcinogenicityNon-carcinogens0.878
BiodegradationNot ready biodegradable0.988
Rat acute toxicity2.6291 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8946
hERG inhibition (predictor II)Inhibitor0.6061
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

Description
This compound belongs to the class of organic compounds known as cyclic peptides. These are compounds containing a cyclic moiety bearing a peptide backbone.
Kingdom
Organic compounds
Super Class
Organic acids and derivatives
Class
Carboxylic acids and derivatives
Sub Class
Amino acids, peptides, and analogues
Direct Parent
Cyclic peptides
Alternative Parents
Dipeptides / Macrolactams / N-formyl-alpha amino acids / Beta amino acids and derivatives / 1-hydroxy-2-unsubstituted benzenoids / Benzene and substituted derivatives / Tertiary carboxylic acid amides / Pyrrolidines / Secondary carboxylic acid amides / Lactams
show 8 more
Substituents
Alpha-dipeptide / Cyclic alpha peptide / Macrolactam / N-formyl-alpha-amino acid / N-formyl-alpha amino acid or derivatives / Beta amino acid or derivatives / Alpha-amino acid or derivatives / 1-hydroxy-2-unsubstituted benzenoid / Phenol / Monocyclic benzene moiety
show 23 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available

Targets

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Serine-type endopeptidase activity
Specific Function
Has activity against the synthetic substrates Boc-Phe-Ser-Arg-Mec, Boc-Leu-Thr-Arg-Mec, Boc-Gln-Ala-Arg-Mec and Boc-Val-Pro-Arg-Mec. The single-chain form is more active than the two-chain form aga...
Gene Name
PRSS1
Uniprot ID
P07477
Uniprot Name
Trypsin-1
Molecular Weight
26557.88 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]
  3. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235]

Drug created on June 13, 2005 07:24 / Updated on March 01, 2020 19:20

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