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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2021-09-11 08:06:19 UTC
Update Date2021-09-26 23:02:41 UTC
HMDB IDHMDB0250948
Secondary Accession NumbersNone
Metabolite Identification
Common NameDehydrodidemnin B
DescriptionN-[10-(butan-2-yl)-8,11,18-trihydroxy-3-[(4-methoxyphenyl)methyl]-2,6,17-trimethyl-20-(2-methylpropyl)-1,4,13,16,21-pentaoxo-15-(propan-2-yl)-1H,2H,3H,4H,6H,7H,10H,11H,12H,13H,15H,16H,17H,20H,21H,23H,24H,25H,25aH-pyrrolo[2,1-f]1,15-dioxa-4,7,10,20-tetraazacyclotricosan-7-yl]-4-methyl-2-{N-methyl-1-[1-(2-oxopropanoyl)pyrrolidin-2-yl]formamido}pentanimidic acid belongs to the class of organic compounds known as cyclic depsipeptides. These are natural or synthetic compounds having sequences of amino and hydroxy carboxylic acid residues (usually α-amino and α-hydroxy acids) connected in a ring. The residues are commonly but not necessarily regularly alternating. Based on a literature review very few articles have been published on N-[10-(butan-2-yl)-8,11,18-trihydroxy-3-[(4-methoxyphenyl)methyl]-2,6,17-trimethyl-20-(2-methylpropyl)-1,4,13,16,21-pentaoxo-15-(propan-2-yl)-1H,2H,3H,4H,6H,7H,10H,11H,12H,13H,15H,16H,17H,20H,21H,23H,24H,25H,25aH-pyrrolo[2,1-f]1,15-dioxa-4,7,10,20-tetraazacyclotricosan-7-yl]-4-methyl-2-{N-methyl-1-[1-(2-oxopropanoyl)pyrrolidin-2-yl]formamido}pentanimidic acid. This compound has been identified in human blood as reported by (PMID: 31557052 ). Dehydrodidemnin b is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Dehydrodidemnin B is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.
Structure
Thumb
Synonyms
ValueSource
N-[10-(Butan-2-yl)-8,11,18-trihydroxy-3-[(4-methoxyphenyl)methyl]-2,6,17-trimethyl-20-(2-methylpropyl)-1,4,13,16,21-pentaoxo-15-(propan-2-yl)-1H,2H,3H,4H,6H,7H,10H,11H,12H,13H,15H,16H,17H,20H,21H,23H,24H,25H,25ah-pyrrolo[2,1-F]1,15-dioxa-4,7,10,20-tetraazacyclotricosan-7-yl]-4-methyl-2-{n-methyl-1-[1-(2-oxopropanoyl)pyrrolidin-2-yl]formamido}pentanimidateGenerator
AplidinMeSH
PlitidepsinMeSH
Chemical FormulaC57H87N7O15
Average Molecular Weight1110.357
Monoisotopic Molecular Weight1109.626015129
IUPAC NameN-[10-(butan-2-yl)-11-hydroxy-3-[(4-methoxyphenyl)methyl]-2,6,17-trimethyl-20-(2-methylpropyl)-1,4,8,13,16,18,21-heptaoxo-15-(propan-2-yl)-docosahydro-1H-pyrrolo[2,1-f]1,15-dioxa-4,7,10,20-tetraazacyclotricosan-7-yl]-4-methyl-2-{N-methyl-1-[1-(2-oxopropanoyl)pyrrolidin-2-yl]formamido}pentanamide
Traditional NameN-{11-hydroxy-15-isopropyl-3-[(4-methoxyphenyl)methyl]-2,6,17-trimethyl-20-(2-methylpropyl)-1,4,8,13,16,18,21-heptaoxo-10-(sec-butyl)-tetradecahydro-3H-pyrrolo[2,1-f]1,15-dioxa-4,7,10,20-tetraazacyclotricosan-7-yl}-4-methyl-2-{N-methyl-1-[1-(2-oxopropanoyl)pyrrolidin-2-yl]formamido}pentanamide
CAS Registry NumberNot Available
SMILES
CCC(C)C1NC(=O)C(NC(=O)C(CC(C)C)N(C)C(=O)C2CCCN2C(=O)C(C)=O)C(C)OC(=O)C(CC2=CC=C(OC)C=C2)N(C)C(=O)C2CCCN2C(=O)C(CC(C)C)NC(=O)C(C)C(=O)C(OC(=O)CC1O)C(C)C
InChI Identifier
InChI=1S/C57H87N7O15/c1-15-33(8)46-44(66)29-45(67)79-49(32(6)7)48(68)34(9)50(69)58-39(26-30(2)3)54(73)64-25-17-19-41(64)56(75)62(13)43(28-37-20-22-38(77-14)23-21-37)57(76)78-36(11)47(52(71)59-46)60-51(70)42(27-31(4)5)61(12)55(74)40-18-16-24-63(40)53(72)35(10)65/h20-23,30-34,36,39-44,46-47,49,66H,15-19,24-29H2,1-14H3,(H,58,69)(H,59,71)(H,60,70)
InChI KeyUUSZLLQJYRSZIS-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as cyclic depsipeptides. These are natural or synthetic compounds having sequences of amino and hydroxy carboxylic acid residues (usually α-amino and α-hydroxy acids) connected in a ring. The residues are commonly but not necessarily regularly alternating.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassPeptidomimetics
Sub ClassDepsipeptides
Direct ParentCyclic depsipeptides
Alternative Parents
Substituents
  • Cyclic depsipeptide
  • Macrolide lactam
  • Leucine or derivatives
  • N-acyl-alpha amino acid or derivatives
  • Macrolactam
  • Proline or derivatives
  • Alpha-amino acid ester
  • Alpha-amino acid amide
  • Alpha-amino acid or derivatives
  • Anisole
  • Pyrrolidine-2-carboxamide
  • Methoxybenzene
  • Pyrrolidine carboxylic acid or derivatives
  • Phenol ether
  • Phenoxy compound
  • N-acylpyrrolidine
  • Alpha-acyloxy ketone
  • Alkyl aryl ether
  • N-acyl-amine
  • 1,3-dicarbonyl compound
  • Dicarboxylic acid or derivatives
  • Benzenoid
  • Fatty acyl
  • Fatty amide
  • Monocyclic benzene moiety
  • Tertiary carboxylic acid amide
  • Pyrrolidine
  • Secondary carboxylic acid amide
  • Carboxamide group
  • Cyclic ketone
  • Carboxylic acid ester
  • Lactone
  • Lactam
  • Secondary alcohol
  • Ketone
  • Oxacycle
  • Azacycle
  • Carboxylic acid derivative
  • Organoheterocyclic compound
  • Ether
  • Organic nitrogen compound
  • Carbonyl group
  • Alcohol
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Organopnictogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxide
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Not Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Spectral PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
logP10(3.07) g/LALOGPS
logP10(3.98) g/LChemAxon
logS10(-4.7) g/LALOGPS
pKa (Strongest Acidic)10.88ChemAxon
pKa (Strongest Basic)-3.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count13ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area284.74 ŲChemAxon
Rotatable Bond Count15ChemAxon
Refractivity288.14 m³·mol⁻¹ChemAxon
Polarizability117.63 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted Spectral Properties

Predicted Kovats Retention Indices

Not Available
Spectra
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID25021302
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound73313844
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]