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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 20:20:43 UTC
Update Date2022-03-07 02:54:29 UTC
HMDB IDHMDB0035367
Secondary Accession Numbers
  • HMDB35367
Metabolite Identification
Common NameCytochalasin Npho
DescriptionCytochalasin Npho belongs to the class of organic compounds known as cytochalasans. These are fungal metabolites structurally characterized by the presence of an isoindolone nucleus fused to a macrocyclic ring, which can either a lactone, as in cytochalasin B, a carbonate, as in cytochalasin E, or a carbocycle, as in cytochalasin D, H, and K. Based on a literature review very few articles have been published on Cytochalasin Npho.
Structure
Data?1563862708
Synonyms
ValueSource
Cytochalasin n?HMDB
3-Benzyl-1,6,12-trihydroxy-4,5,10,12-tetramethyl-3H,6H,6ah,9H,10H,11H,12H,15H,15BH-cycloundeca[e]isoindol-15-yl acetic acidGenerator
Chemical FormulaC30H39NO5
Average Molecular Weight493.6344
Monoisotopic Molecular Weight493.282823363
IUPAC Name3-benzyl-6,12-dihydroxy-4,5,10,12-tetramethyl-1-oxo-1H,2H,3H,6H,6aH,9H,10H,11H,12H,15H,15bH-cycloundeca[e]isoindol-15-yl acetate
Traditional Name3-benzyl-6,12-dihydroxy-4,5,10,12-tetramethyl-1-oxo-2H,3H,6H,6aH,9H,10H,11H,15H,15bH-cycloundeca[e]isoindol-15-yl acetate
CAS Registry Number108050-28-8
SMILES
CC1C\C=C\C2C(O)C(C)=C(C)C3C(CC4=CC=CC=C4)NC(=O)C23C(OC(C)=O)\C=C/C(C)(O)C1
InChI Identifier
InChI=1S/C30H39NO5/c1-18-10-9-13-23-27(33)20(3)19(2)26-24(16-22-11-7-6-8-12-22)31-28(34)30(23,26)25(36-21(4)32)14-15-29(5,35)17-18/h6-9,11-15,18,23-27,33,35H,10,16-17H2,1-5H3,(H,31,34)/b13-9+,15-14-
InChI KeyWFSYATBEJTUDQA-WISUYLHISA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as cytochalasans. These are fungal metabolites structurally characterized by the presence of an isoindolone nucleus fused to a macrocyclic ring, which can either a lactone, as in cytochalasin B, a carbonate, as in cytochalasin E, or a carbocycle, as in cytochalasin D, H, and K.
KingdomOrganic compounds
Super ClassAlkaloids and derivatives
ClassCytochalasans
Sub ClassNot Available
Direct ParentCytochalasans
Alternative Parents
Substituents
  • Carbocyclic cytochalasan skeleton
  • Cytochalasan
  • Isoindolone
  • Isoindoline
  • Isoindole
  • Isoindole or derivatives
  • Monocyclic benzene moiety
  • Benzenoid
  • Pyrrolidone
  • 2-pyrrolidone
  • Pyrrolidine
  • Tertiary alcohol
  • Secondary alcohol
  • Secondary carboxylic acid amide
  • Carboxamide group
  • Carboxylic acid ester
  • Lactam
  • Organoheterocyclic compound
  • Azacycle
  • Carboxylic acid derivative
  • Monocarboxylic acid or derivatives
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Carbonyl group
  • Organonitrogen compound
  • Organooxygen compound
  • Alcohol
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point253 - 254 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.0034 g/LALOGPS
logP3.66ALOGPS
logP3.27ChemAxon
logS-5.2ALOGPS
pKa (Strongest Acidic)13.92ChemAxon
pKa (Strongest Basic)-0.53ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area95.86 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity141.76 m³·mol⁻¹ChemAxon
Polarizability55.05 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+218.55231661259
DarkChem[M-H]-205.67131661259
DeepCCS[M-2H]-260.16830932474
DeepCCS[M+Na]+235.73130932474
AllCCS[M+H]+221.032859911
AllCCS[M+H-H2O]+219.032859911
AllCCS[M+NH4]+222.832859911
AllCCS[M+Na]+223.332859911
AllCCS[M-H]-221.832859911
AllCCS[M+Na-2H]-223.732859911
AllCCS[M+HCOO]-226.032859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Cytochalasin NphoCC1C\C=C\C2C(O)C(C)=C(C)C3C(CC4=CC=CC=C4)NC(=O)C23C(OC(C)=O)\C=C/C(C)(O)C14674.0Standard polar33892256
Cytochalasin NphoCC1C\C=C\C2C(O)C(C)=C(C)C3C(CC4=CC=CC=C4)NC(=O)C23C(OC(C)=O)\C=C/C(C)(O)C13542.6Standard non polar33892256
Cytochalasin NphoCC1C\C=C\C2C(O)C(C)=C(C)C3C(CC4=CC=CC=C4)NC(=O)C23C(OC(C)=O)\C=C/C(C)(O)C13620.9Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Cytochalasin Npho,1TMS,isomer #1CC(=O)OC1/C=C\C(C)(O)CC(C)C/C=C/C2C(O[Si](C)(C)C)C(C)=C(C)C3C(CC4=CC=CC=C4)NC(=O)C1233643.5Semi standard non polar33892256
Cytochalasin Npho,1TMS,isomer #2CC(=O)OC1/C=C\C(C)(O[Si](C)(C)C)CC(C)C/C=C/C2C(O)C(C)=C(C)C3C(CC4=CC=CC=C4)NC(=O)C1233704.1Semi standard non polar33892256
Cytochalasin Npho,1TMS,isomer #3CC(=O)OC1/C=C\C(C)(O)CC(C)C/C=C/C2C(O)C(C)=C(C)C3C(CC4=CC=CC=C4)N([Si](C)(C)C)C(=O)C1233606.6Semi standard non polar33892256
Cytochalasin Npho,2TMS,isomer #1CC(=O)OC1/C=C\C(C)(O[Si](C)(C)C)CC(C)C/C=C/C2C(O[Si](C)(C)C)C(C)=C(C)C3C(CC4=CC=CC=C4)NC(=O)C1233590.3Semi standard non polar33892256
Cytochalasin Npho,2TMS,isomer #2CC(=O)OC1/C=C\C(C)(O)CC(C)C/C=C/C2C(O[Si](C)(C)C)C(C)=C(C)C3C(CC4=CC=CC=C4)N([Si](C)(C)C)C(=O)C1233537.0Semi standard non polar33892256
Cytochalasin Npho,2TMS,isomer #3CC(=O)OC1/C=C\C(C)(O[Si](C)(C)C)CC(C)C/C=C/C2C(O)C(C)=C(C)C3C(CC4=CC=CC=C4)N([Si](C)(C)C)C(=O)C1233568.6Semi standard non polar33892256
Cytochalasin Npho,3TMS,isomer #1CC(=O)OC1/C=C\C(C)(O[Si](C)(C)C)CC(C)C/C=C/C2C(O[Si](C)(C)C)C(C)=C(C)C3C(CC4=CC=CC=C4)N([Si](C)(C)C)C(=O)C1233530.7Semi standard non polar33892256
Cytochalasin Npho,3TMS,isomer #1CC(=O)OC1/C=C\C(C)(O[Si](C)(C)C)CC(C)C/C=C/C2C(O[Si](C)(C)C)C(C)=C(C)C3C(CC4=CC=CC=C4)N([Si](C)(C)C)C(=O)C1233520.7Standard non polar33892256
Cytochalasin Npho,1TBDMS,isomer #1CC(=O)OC1/C=C\C(C)(O)CC(C)C/C=C/C2C(O[Si](C)(C)C(C)(C)C)C(C)=C(C)C3C(CC4=CC=CC=C4)NC(=O)C1233864.8Semi standard non polar33892256
Cytochalasin Npho,1TBDMS,isomer #2CC(=O)OC1/C=C\C(C)(O[Si](C)(C)C(C)(C)C)CC(C)C/C=C/C2C(O)C(C)=C(C)C3C(CC4=CC=CC=C4)NC(=O)C1233940.6Semi standard non polar33892256
Cytochalasin Npho,1TBDMS,isomer #3CC(=O)OC1/C=C\C(C)(O)CC(C)C/C=C/C2C(O)C(C)=C(C)C3C(CC4=CC=CC=C4)N([Si](C)(C)C(C)(C)C)C(=O)C1233855.5Semi standard non polar33892256
Cytochalasin Npho,2TBDMS,isomer #1CC(=O)OC1/C=C\C(C)(O[Si](C)(C)C(C)(C)C)CC(C)C/C=C/C2C(O[Si](C)(C)C(C)(C)C)C(C)=C(C)C3C(CC4=CC=CC=C4)NC(=O)C1234036.8Semi standard non polar33892256
Cytochalasin Npho,2TBDMS,isomer #2CC(=O)OC1/C=C\C(C)(O)CC(C)C/C=C/C2C(O[Si](C)(C)C(C)(C)C)C(C)=C(C)C3C(CC4=CC=CC=C4)N([Si](C)(C)C(C)(C)C)C(=O)C1233993.6Semi standard non polar33892256
Cytochalasin Npho,2TBDMS,isomer #3CC(=O)OC1/C=C\C(C)(O[Si](C)(C)C(C)(C)C)CC(C)C/C=C/C2C(O)C(C)=C(C)C3C(CC4=CC=CC=C4)N([Si](C)(C)C(C)(C)C)C(=O)C1234046.8Semi standard non polar33892256
Cytochalasin Npho,3TBDMS,isomer #1CC(=O)OC1/C=C\C(C)(O[Si](C)(C)C(C)(C)C)CC(C)C/C=C/C2C(O[Si](C)(C)C(C)(C)C)C(C)=C(C)C3C(CC4=CC=CC=C4)N([Si](C)(C)C(C)(C)C)C(=O)C1234203.2Semi standard non polar33892256
Cytochalasin Npho,3TBDMS,isomer #1CC(=O)OC1/C=C\C(C)(O[Si](C)(C)C(C)(C)C)CC(C)C/C=C/C2C(O[Si](C)(C)C(C)(C)C)C(C)=C(C)C3C(CC4=CC=CC=C4)N([Si](C)(C)C(C)(C)C)C(=O)C1234031.7Standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Cytochalasin Npho GC-MS (Non-derivatized) - 70eV, Positivesplash10-0036-9001700000-ccb3b677aaf655efdd522017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Cytochalasin Npho GC-MS (2 TMS) - 70eV, Positivesplash10-00fr-8000093000-2672d3ce2062c3418e0b2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Cytochalasin Npho GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cytochalasin Npho 10V, Positive-QTOFsplash10-004l-0000900000-a887a58c18dbefb347da2016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cytochalasin Npho 20V, Positive-QTOFsplash10-003r-1000900000-6a1c878ec99dc2b455572016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cytochalasin Npho 40V, Positive-QTOFsplash10-0pbc-8902400000-8e4f29fec6fd370499bd2016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cytochalasin Npho 10V, Negative-QTOFsplash10-0006-1000900000-1191b7343df6d6b448722016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cytochalasin Npho 20V, Negative-QTOFsplash10-0khc-2000900000-32310d51739119b187f72016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cytochalasin Npho 40V, Negative-QTOFsplash10-0006-9036300000-5183c0a016d1038c2f192016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cytochalasin Npho 10V, Negative-QTOFsplash10-0a4i-9000000000-c01bbbf5bed889264ddb2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cytochalasin Npho 20V, Negative-QTOFsplash10-0a4i-9000000000-c01bbbf5bed889264ddb2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cytochalasin Npho 40V, Negative-QTOFsplash10-052f-9000000000-2dee1995aa51e221300f2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cytochalasin Npho 10V, Positive-QTOFsplash10-00mo-0000900000-b7d2c978208cf4a488fe2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cytochalasin Npho 20V, Positive-QTOFsplash10-016r-0000900000-ccf8da00f7c7629e69a52021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cytochalasin Npho 40V, Positive-QTOFsplash10-0006-2206900000-a6b42b2c43ecc50977d32021-09-25Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB014040
KNApSAcK IDC00011339
Chemspider ID35013911
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound131751725
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. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .