Desvancosaminyl vancomycin

Identification

Generic Name
Desvancosaminyl vancomycin
DrugBank Accession Number
DB04529
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
Weight
Average: 1306.08
Monoisotopic: 1304.3355711
Chemical Formula
C59H62Cl2N8O22
Synonyms
  • Pseudovancomycin
  • Vancomycin pseudoaglycone

Pharmacology

Indication

Not Available

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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UDesvancosaminyl-vancomycin vancosaminetransferaseNot AvailableAmycolatopsis orientalis
UdTDP-epi-vancosaminyltransferaseNot AvailableAmycolatopsis orientalis
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

Adverse Effects
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Toxicity

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

Categories

Drug Categories
Not Available
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as oligopeptides. These are organic compounds containing a sequence of between three and ten alpha-amino acids joined by peptide bonds.
Kingdom
Organic compounds
Super Class
Organic acids and derivatives
Class
Carboxylic acids and derivatives
Sub Class
Amino acids, peptides, and analogues
Direct Parent
Oligopeptides
Alternative Parents
Cyclic peptides / Phenolic glycosides / Leucine and derivatives / N-acyl-alpha amino acids and derivatives / Hexoses / Alpha amino acid amides / Diarylethers / O-glycosyl compounds / 1-hydroxy-2-unsubstituted benzenoids / 1-hydroxy-4-unsubstituted benzenoids
show 21 more
Substituents
1-hydroxy-2-unsubstituted benzenoid / 1-hydroxy-4-unsubstituted benzenoid / Acetal / Alcohol / Alpha-amino acid amide / Alpha-amino acid or derivatives / Alpha-oligopeptide / Amine / Amino acid / Amino acid or derivatives
show 43 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
organochlorine compound, monosaccharide derivative, polyphenol, heterodetic cyclic peptide, cyclic ether, glycopeptide (CHEBI:47395)
Affected organisms
Not Available

Chemical Identifiers

UNII
Not Available
CAS number
101485-50-1
InChI Key
QCHYVJAUGVHJHX-PZIRYZLHSA-N
InChI
InChI=1S/C59H62Cl2N8O22/c1-20(2)10-30(63-3)52(80)68-44-46(75)22-5-8-34(28(60)12-22)88-36-14-24-15-37(51(36)91-59-50(79)49(78)48(77)38(19-70)90-59)89-35-9-6-23(13-29(35)61)47(76)45-57(85)67-43(58(86)87)27-16-25(71)17-33(73)40(27)26-11-21(4-7-32(26)72)41(54(82)69-45)66-55(83)42(24)65-53(81)31(18-39(62)74)64-56(44)84/h4-9,11-17,20,30-31,38,41-50,59,63,70-73,75-79H,10,18-19H2,1-3H3,(H2,62,74)(H,64,84)(H,65,81)(H,66,83)(H,67,85)(H,68,80)(H,69,82)(H,86,87)/t30-,31+,38-,41-,42-,43+,44-,45+,46-,47-,48-,49+,50-,59+/m1/s1
IUPAC Name
(1S,2R,18R,19R,22S,25R,28R,40S)-22-(carbamoylmethyl)-5,47-dichloro-2,18,32,35,37-pentahydroxy-19-[(2R)-4-methyl-2-(methylamino)pentanamido]-20,23,26,42,44-pentaoxo-48-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-7,13-dioxa-21,24,27,41,43-pentaazaoctacyclo[26.14.2.2^{3,6}.2^{14,17}.1^{8,12}.1^{29,33}.0^{10,25}.0^{34,39}]pentaconta-3,5,8,10,12(48),14,16,29(45),30,32,34,36,38,46,49-pentadecaene-40-carboxylic acid
SMILES
CN[C@H](CC(C)C)C(=O)N[C@@H]1[C@H](O)C2=CC=C(OC3=C(O[C@@H]4O[C@H](CO)[C@@H](O)[C@H](O)[C@H]4O)C4=CC(=C3)[C@@H](NC(=O)[C@H](CC(N)=O)NC1=O)C(=O)N[C@@H]1C3=CC(=C(O)C=C3)C3=C(O)C=C(O)C=C3[C@H](NC(=O)[C@@H](NC1=O)[C@H](O)C1=CC(Cl)=C(O4)C=C1)C(O)=O)C(Cl)=C2

References

General References
Not Available
PubChem Compound
447876
PubChem Substance
46507259
ChemSpider
394844
ChEBI
47395

Clinical Trials

Clinical Trials
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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 Solubility0.226 mg/mLALOGPS
logP1.6ALOGPS
logP-4Chemaxon
logS-3.8ALOGPS
pKa (Strongest Acidic)3.08Chemaxon
pKa (Strongest Basic)8.89Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count21Chemaxon
Hydrogen Donor Count18Chemaxon
Polar Surface Area486.01 Å2Chemaxon
Rotatable Bond Count11Chemaxon
Refractivity310.95 m3·mol-1Chemaxon
Polarizability122.1 Å3Chemaxon
Number of Rings9Chemaxon
Bioavailability0Chemaxon
Rule of FiveNoChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleYesChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption-0.6585
Blood Brain Barrier-0.9912
Caco-2 permeable-0.7221
P-glycoprotein substrateSubstrate0.8112
P-glycoprotein inhibitor INon-inhibitor0.8702
P-glycoprotein inhibitor IINon-inhibitor0.9799
Renal organic cation transporterNon-inhibitor0.9502
CYP450 2C9 substrateNon-substrate0.842
CYP450 2D6 substrateNon-substrate0.8321
CYP450 3A4 substrateSubstrate0.6331
CYP450 1A2 substrateNon-inhibitor0.9005
CYP450 2C9 inhibitorNon-inhibitor0.8935
CYP450 2D6 inhibitorNon-inhibitor0.9168
CYP450 2C19 inhibitorNon-inhibitor0.8863
CYP450 3A4 inhibitorNon-inhibitor0.7683
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.827
Ames testNon AMES toxic0.6584
CarcinogenicityNon-carcinogens0.8953
BiodegradationNot ready biodegradable0.9975
Rat acute toxicity2.5447 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.997
hERG inhibition (predictor II)Non-inhibitor0.7908
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/MSsplash10-004i-0942000000-c2791bb57e38db2f1a66
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0f79-0797000000-54104412134de4bfbfe8
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-00n0-1691000000-6d040f455a30784f2ec3
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0a4u-1960000000-cf5bcd2aa47c07c42809
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-02wi-7920000000-ce447a04c8f50ceb163f
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-03dj-9300000001-ae82ab7ea2b4c39b138a
Chromatographic Properties
Collision Cross Sections (CCS)
Not Available

Targets

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Kind
Protein
Organism
Amycolatopsis orientalis
Pharmacological action
Unknown
General Function
Catalyzes the attachment of L-vancosamine to a monoglucosylated heptapeptide intermediate during the final stage of glycopeptide antibiotic vancomycin biosynthesis.
Specific Function
enzyme binding
Gene Name
gtfD
Uniprot ID
Q9AFC7
Uniprot Name
Desvancosaminyl-vancomycin vancosaminetransferase
Molecular Weight
42880.545 Da
Kind
Protein
Organism
Amycolatopsis orientalis
Pharmacological action
Unknown
General Function
Catalyzes the attachment of 4-epi-vancosamine from a TDP donor to the beta-OH-Tyr-6 of the aglycone cosubstrate in the biosynthesis of glycopeptide antibiotic chloroeremomycin, a member of the vancomycin group of antibiotics. Strongly prefers devancoaminyl-vancomycin (DVV) as substrate rather than the heptapeptide vancomycin aglycone (AGV). Acts downstream of GtfB.
Specific Function
enzyme binding
Gene Name
gtfA
Uniprot ID
P96558
Uniprot Name
dTDP-epi-vancosaminyltransferase
Molecular Weight
41661.965 Da

Drug created at June 13, 2005 13:24 / Updated at June 12, 2020 16:52