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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2012-09-11 17:43:22 UTC
Update Date2022-03-07 02:52:59 UTC
HMDB IDHMDB0031452
Secondary Accession Numbers
  • HMDB31452
Metabolite Identification
Common NameLignans
DescriptionLignans, also known as neolignans, belongs to the class of organic compounds known as podophyllotoxins. These are tetralin lignans in which the benzene moiety of the tetralin skeleton is fused to a 1,3-dioxolane and the cyclohexane is fused to a butyrolactone (pyrrolidin-2-one). Lignans has been detected, but not quantified in, several different foods, such as wheats (Triticum), ryes (Secale cereale), quinoas (Chenopodium quinoa), hard wheats (Triticum durum), and soy beans (Glycine max). This could make lignans a potential biomarker for the consumption of these foods. Based on a literature review a small amount of articles have been published on Lignans.
Structure
Data?1563862127
Synonyms
ValueSource
NeolignansMeSH
LignanMeSH
NeolignanMeSH
PicropodophyllotoxinHMDB
PodophyllotoxinHMDB
LignansMeSH
Chemical FormulaC22H22O8
Average Molecular Weight414.4053
Monoisotopic Molecular Weight414.13146768
IUPAC Name(10R,11S,16R)-16-hydroxy-10-(3,4,5-trimethoxyphenyl)-4,6,13-trioxatetracyclo[7.7.0.0³,⁷.0¹¹,¹⁵]hexadeca-1,3(7),8-trien-12-one
Traditional Nameepipodophyllotoxins
CAS Registry NumberNot Available
SMILES
COC1=CC(=CC(OC)=C1OC)[C@H]1[C@H]2C(COC2=O)[C@@H](O)C2=CC3=C(OCO3)C=C12
InChI Identifier
InChI=1S/C22H22O8/c1-25-16-4-10(5-17(26-2)21(16)27-3)18-11-6-14-15(30-9-29-14)7-12(11)20(23)13-8-28-22(24)19(13)18/h4-7,13,18-20,23H,8-9H2,1-3H3/t13?,18-,19-,20+/m1/s1
InChI KeyYJGVMLPVUAXIQN-BCVBHCCTSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as podophyllotoxins. These are tetralin lignans in which the benzene moiety of the tetralin skeleton is fused to a 1,3-dioxolane and the cyclohexane is fused to a butyrolactone (pyrrolidin-2-one).
KingdomOrganic compounds
Super ClassLignans, neolignans and related compounds
ClassLignan lactones
Sub ClassPodophyllotoxins
Direct ParentPodophyllotoxins
Alternative Parents
Substituents
  • Podophyllotoxin
  • 1-aryltetralin lignan
  • Linear furanonaphthodioxole
  • Naphthofuran
  • Tetralin
  • Benzodioxole
  • Phenoxy compound
  • Phenol ether
  • Anisole
  • Methoxybenzene
  • Alkyl aryl ether
  • Monocyclic benzene moiety
  • Benzenoid
  • Gamma butyrolactone
  • Tetrahydrofuran
  • Secondary alcohol
  • Carboxylic acid ester
  • Lactone
  • Monocarboxylic acid or derivatives
  • Organoheterocyclic compound
  • Ether
  • Oxacycle
  • Carboxylic acid derivative
  • Acetal
  • Organic oxygen compound
  • Carbonyl group
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Alcohol
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point228 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.1 mg/mL at 25 °CNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.11 g/LALOGPS
logP2.37ALOGPS
logP1.62ChemAxon
logS-3.6ALOGPS
pKa (Strongest Acidic)14.02ChemAxon
pKa (Strongest Basic)-3.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area92.68 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity103.9 m³·mol⁻¹ChemAxon
Polarizability41.66 ųChemAxon
Number of Rings5ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+197.76931661259
DarkChem[M-H]-193.36331661259
DeepCCS[M-2H]-225.70430932474
DeepCCS[M+Na]+201.12930932474
AllCCS[M+H]+196.032859911
AllCCS[M+H-H2O]+193.332859911
AllCCS[M+NH4]+198.432859911
AllCCS[M+Na]+199.132859911
AllCCS[M-H]-199.432859911
AllCCS[M+Na-2H]-199.432859911
AllCCS[M+HCOO]-199.632859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
LignansCOC1=CC(=CC(OC)=C1OC)[C@H]1[C@H]2C(COC2=O)[C@@H](O)C2=CC3=C(OCO3)C=C125169.2Standard polar33892256
LignansCOC1=CC(=CC(OC)=C1OC)[C@H]1[C@H]2C(COC2=O)[C@@H](O)C2=CC3=C(OCO3)C=C123345.7Standard non polar33892256
LignansCOC1=CC(=CC(OC)=C1OC)[C@H]1[C@H]2C(COC2=O)[C@@H](O)C2=CC3=C(OCO3)C=C123477.7Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Lignans,1TMS,isomer #1COC1=CC([C@@H]2C3=CC4=C(C=C3[C@H](O[Si](C)(C)C)C3COC(=O)[C@H]32)OCO4)=CC(OC)=C1OC3326.9Semi standard non polar33892256
Lignans,1TBDMS,isomer #1COC1=CC([C@@H]2C3=CC4=C(C=C3[C@H](O[Si](C)(C)C(C)(C)C)C3COC(=O)[C@H]32)OCO4)=CC(OC)=C1OC3564.8Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Lignans GC-MS (Non-derivatized) - 70eV, Positivesplash10-005j-0109000000-14f78dbe46f8312a8fb52017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Lignans GC-MS (1 TMS) - 70eV, Positivesplash10-0kmi-1003900000-d43e5f990afbda30580d2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Lignans GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Lignans 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 - Lignans 10V, Positive-QTOFsplash10-00kb-0009500000-4616d49ee91153709c322016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lignans 20V, Positive-QTOFsplash10-014j-0029100000-07a109dcecbceb6115342016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lignans 40V, Positive-QTOFsplash10-0gc0-0029000000-866502321774872dbd1f2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lignans 10V, Negative-QTOFsplash10-03di-0003900000-0a5bb4d2c68362569d3c2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lignans 20V, Negative-QTOFsplash10-02ta-0009200000-dc7b8f1ae65bdd58832d2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lignans 40V, Negative-QTOFsplash10-014j-1039000000-d11a736e9337d8575e1e2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lignans 10V, Positive-QTOFsplash10-014i-0020900000-1608d78c8539edf244232021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lignans 20V, Positive-QTOFsplash10-014i-0043900000-e81bc57018acf33199a42021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lignans 40V, Positive-QTOFsplash10-02vi-0039000000-552005d9b6b201ff35632021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lignans 10V, Negative-QTOFsplash10-03di-0100900000-ec8194ed366395157a1b2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lignans 20V, Negative-QTOFsplash10-00lr-0009100000-bcb75b5aa88155a814142021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lignans 40V, Negative-QTOFsplash10-004i-2019100000-98fbf20ab2f57af371642021-09-24Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen Locations
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
UrineDetected and Quantified0.246 +/- 0.269 umol/mmol creatinineAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified0.161 +/- 0.135 umol/mmol creatinineAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified1.373 +/- 2.313 umol/mmol creatinineAdult (>18 years old)Female
Normal
details
UrineDetected and Quantified0.331 +/- 0.419 umol/mmol creatinineAdult (>18 years old)BothNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB005955
KNApSAcK IDC00002619 C00033300
Chemspider ID391314
KEGG Compound IDC10871
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkLignan
METLIN IDNot Available
PubChem Compound443013
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. Lima LM, Perazzo FF, Tavares Carvalho JC, Bastos JK: Anti-inflammatory and analgesic activities of the ethanolic extracts from Zanthoxylum riedelianum (Rutaceae) leaves and stem bark. J Pharm Pharmacol. 2007 Aug;59(8):1151-8. [PubMed:17725859 ]
  2. Valimaa AL, Honkalampi-Hamalainen U, Pietarinen S, Willfor S, Holmbom B, von Wright A: Antimicrobial and cytotoxic knotwood extracts and related pure compounds and their effects on food-associated microorganisms. Int J Food Microbiol. 2007 Apr 10;115(2):235-43. Epub 2006 Dec 22. [PubMed:17188387 ]
  3. Ma CJ, Sung SH, Kim YC: New neuroprotective dibenzylbutane lignans isolated from Machilus thunbergii. Nat Prod Res. 2010 Apr;24(6):562-8. doi: 10.1080/14786410902823279. [PubMed:20397106 ]
  4. Kassuya CA, Leite DF, de Melo LV, Rehder VL, Calixto JB: Anti-inflammatory properties of extracts, fractions and lignans isolated from Phyllanthus amarus. Planta Med. 2005 Aug;71(8):721-6. [PubMed:16142635 ]
  5. (). Duke, James A. (1992) Handbook of phytochemical constituents of GRAS herbs and other economic plants. Boca Raton, FL. CRC Press.. .