Hmdb loader
Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2021-08-28 20:24:44 UTC
Update Date2021-09-26 22:48:54 UTC
HMDB IDHMDB0242253
Secondary Accession NumbersNone
Metabolite Identification
Common Name(+)-Isofebrifugine
Description3-[3-(3-hydroxypiperidin-2-yl)-2-oxopropyl]-3,4-dihydroquinazolin-4-one belongs to the class of organic compounds known as quinazolines. Quinazolines are compounds containing a quinazoline moiety, which is made up of two fused six-member aromatic rings, a benzene ring and a pyrimidine ring. Based on a literature review very few articles have been published on 3-[3-(3-hydroxypiperidin-2-yl)-2-oxopropyl]-3,4-dihydroquinazolin-4-one. This compound has been identified in human blood as reported by (PMID: 31557052 ). (+)-isofebrifugine is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically (+)-Isofebrifugine 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
IsofebrifugineMeSH, HMDB
Chemical FormulaC16H19N3O3
Average Molecular Weight301.346
Monoisotopic Molecular Weight301.142641484
IUPAC Name3-[3-(3-hydroxypiperidin-2-yl)-2-oxopropyl]-3,4-dihydroquinazolin-4-one
Traditional Namegamma-dichroine
CAS Registry NumberNot Available
SMILES
OC1CCCNC1CC(=O)CN1C=NC2=CC=CC=C2C1=O
InChI Identifier
InChI=1S/C16H19N3O3/c20-11(8-14-15(21)6-3-7-17-14)9-19-10-18-13-5-2-1-4-12(13)16(19)22/h1-2,4-5,10,14-15,17,21H,3,6-9H2
InChI KeyFWVHWDSCPKXMDB-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as quinazolines. Quinazolines are compounds containing a quinazoline moiety, which is made up of two fused six-member aromatic rings, a benzene ring and a pyrimidine ring.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassDiazanaphthalenes
Sub ClassBenzodiazines
Direct ParentQuinazolines
Alternative Parents
Substituents
  • Quinazoline
  • Pyrimidone
  • Beta-aminoketone
  • Piperidine
  • Pyrimidine
  • Benzenoid
  • Heteroaromatic compound
  • 1,2-aminoalcohol
  • Ketone
  • Lactam
  • Secondary alcohol
  • Secondary aliphatic amine
  • Azacycle
  • Secondary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxide
  • Organopnictogen compound
  • Organic nitrogen compound
  • Carbonyl group
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Alcohol
  • Amine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot 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 Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
logP0.01ALOGPS
logP0.34ChemAxon
logS-2.9ALOGPS
pKa (Strongest Acidic)14.48ChemAxon
pKa (Strongest Basic)9.28ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area82 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity83.44 m³·mol⁻¹ChemAxon
Polarizability30.43 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+164.34230932474
DeepCCS[M-H]-161.98430932474
DeepCCS[M-2H]-194.8730932474
DeepCCS[M+Na]+170.43530932474
AllCCS[M+H]+171.532859911
AllCCS[M+H-H2O]+168.132859911
AllCCS[M+NH4]+174.632859911
AllCCS[M+Na]+175.532859911
AllCCS[M-H]-174.032859911
AllCCS[M+Na-2H]-173.832859911
AllCCS[M+HCOO]-173.832859911

Predicted Kovats Retention Indices

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
(+)-Isofebrifugine,1TMS,isomer #1C[Si](C)(C)OC1CCCNC1CC(=O)CN1C=NC2=CC=CC=C2C1=O2902.0Semi standard non polar33892256
(+)-Isofebrifugine,1TMS,isomer #1C[Si](C)(C)OC1CCCNC1CC(=O)CN1C=NC2=CC=CC=C2C1=O2823.6Standard non polar33892256
(+)-Isofebrifugine,1TMS,isomer #1C[Si](C)(C)OC1CCCNC1CC(=O)CN1C=NC2=CC=CC=C2C1=O3772.9Standard polar33892256
(+)-Isofebrifugine,1TMS,isomer #2C[Si](C)(C)OC(=CN1C=NC2=CC=CC=C2C1=O)CC1NCCCC1O3048.9Semi standard non polar33892256
(+)-Isofebrifugine,1TMS,isomer #2C[Si](C)(C)OC(=CN1C=NC2=CC=CC=C2C1=O)CC1NCCCC1O2818.6Standard non polar33892256
(+)-Isofebrifugine,1TMS,isomer #2C[Si](C)(C)OC(=CN1C=NC2=CC=CC=C2C1=O)CC1NCCCC1O4177.0Standard polar33892256
(+)-Isofebrifugine,1TMS,isomer #3C[Si](C)(C)OC(=CC1NCCCC1O)CN1C=NC2=CC=CC=C2C1=O3008.6Semi standard non polar33892256
(+)-Isofebrifugine,1TMS,isomer #3C[Si](C)(C)OC(=CC1NCCCC1O)CN1C=NC2=CC=CC=C2C1=O2857.9Standard non polar33892256
(+)-Isofebrifugine,1TMS,isomer #3C[Si](C)(C)OC(=CC1NCCCC1O)CN1C=NC2=CC=CC=C2C1=O4049.0Standard polar33892256
(+)-Isofebrifugine,1TMS,isomer #4C[Si](C)(C)N1CCCC(O)C1CC(=O)CN1C=NC2=CC=CC=C2C1=O2950.7Semi standard non polar33892256
(+)-Isofebrifugine,1TMS,isomer #4C[Si](C)(C)N1CCCC(O)C1CC(=O)CN1C=NC2=CC=CC=C2C1=O2898.0Standard non polar33892256
(+)-Isofebrifugine,1TMS,isomer #4C[Si](C)(C)N1CCCC(O)C1CC(=O)CN1C=NC2=CC=CC=C2C1=O3891.7Standard polar33892256
(+)-Isofebrifugine,2TMS,isomer #1C[Si](C)(C)OC(=CN1C=NC2=CC=CC=C2C1=O)CC1NCCCC1O[Si](C)(C)C2969.8Semi standard non polar33892256
(+)-Isofebrifugine,2TMS,isomer #1C[Si](C)(C)OC(=CN1C=NC2=CC=CC=C2C1=O)CC1NCCCC1O[Si](C)(C)C2888.3Standard non polar33892256
(+)-Isofebrifugine,2TMS,isomer #1C[Si](C)(C)OC(=CN1C=NC2=CC=CC=C2C1=O)CC1NCCCC1O[Si](C)(C)C3749.2Standard polar33892256
(+)-Isofebrifugine,2TMS,isomer #2C[Si](C)(C)OC(=CC1NCCCC1O[Si](C)(C)C)CN1C=NC2=CC=CC=C2C1=O2943.3Semi standard non polar33892256
(+)-Isofebrifugine,2TMS,isomer #2C[Si](C)(C)OC(=CC1NCCCC1O[Si](C)(C)C)CN1C=NC2=CC=CC=C2C1=O2896.2Standard non polar33892256
(+)-Isofebrifugine,2TMS,isomer #2C[Si](C)(C)OC(=CC1NCCCC1O[Si](C)(C)C)CN1C=NC2=CC=CC=C2C1=O3658.1Standard polar33892256
(+)-Isofebrifugine,2TMS,isomer #3C[Si](C)(C)OC1CCCN([Si](C)(C)C)C1CC(=O)CN1C=NC2=CC=CC=C2C1=O2914.2Semi standard non polar33892256
(+)-Isofebrifugine,2TMS,isomer #3C[Si](C)(C)OC1CCCN([Si](C)(C)C)C1CC(=O)CN1C=NC2=CC=CC=C2C1=O2961.5Standard non polar33892256
(+)-Isofebrifugine,2TMS,isomer #3C[Si](C)(C)OC1CCCN([Si](C)(C)C)C1CC(=O)CN1C=NC2=CC=CC=C2C1=O3620.6Standard polar33892256
(+)-Isofebrifugine,2TMS,isomer #4C[Si](C)(C)OC(=CN1C=NC2=CC=CC=C2C1=O)CC1C(O)CCCN1[Si](C)(C)C2983.0Semi standard non polar33892256
(+)-Isofebrifugine,2TMS,isomer #4C[Si](C)(C)OC(=CN1C=NC2=CC=CC=C2C1=O)CC1C(O)CCCN1[Si](C)(C)C3016.6Standard non polar33892256
(+)-Isofebrifugine,2TMS,isomer #4C[Si](C)(C)OC(=CN1C=NC2=CC=CC=C2C1=O)CC1C(O)CCCN1[Si](C)(C)C3888.5Standard polar33892256
(+)-Isofebrifugine,2TMS,isomer #5C[Si](C)(C)OC(=CC1C(O)CCCN1[Si](C)(C)C)CN1C=NC2=CC=CC=C2C1=O2961.8Semi standard non polar33892256
(+)-Isofebrifugine,2TMS,isomer #5C[Si](C)(C)OC(=CC1C(O)CCCN1[Si](C)(C)C)CN1C=NC2=CC=CC=C2C1=O2998.1Standard non polar33892256
(+)-Isofebrifugine,2TMS,isomer #5C[Si](C)(C)OC(=CC1C(O)CCCN1[Si](C)(C)C)CN1C=NC2=CC=CC=C2C1=O3813.2Standard polar33892256
(+)-Isofebrifugine,3TMS,isomer #1C[Si](C)(C)OC(=CN1C=NC2=CC=CC=C2C1=O)CC1C(O[Si](C)(C)C)CCCN1[Si](C)(C)C2983.9Semi standard non polar33892256
(+)-Isofebrifugine,3TMS,isomer #1C[Si](C)(C)OC(=CN1C=NC2=CC=CC=C2C1=O)CC1C(O[Si](C)(C)C)CCCN1[Si](C)(C)C3046.2Standard non polar33892256
(+)-Isofebrifugine,3TMS,isomer #1C[Si](C)(C)OC(=CN1C=NC2=CC=CC=C2C1=O)CC1C(O[Si](C)(C)C)CCCN1[Si](C)(C)C3621.9Standard polar33892256
(+)-Isofebrifugine,3TMS,isomer #2C[Si](C)(C)OC(=CC1C(O[Si](C)(C)C)CCCN1[Si](C)(C)C)CN1C=NC2=CC=CC=C2C1=O2972.8Semi standard non polar33892256
(+)-Isofebrifugine,3TMS,isomer #2C[Si](C)(C)OC(=CC1C(O[Si](C)(C)C)CCCN1[Si](C)(C)C)CN1C=NC2=CC=CC=C2C1=O3028.3Standard non polar33892256
(+)-Isofebrifugine,3TMS,isomer #2C[Si](C)(C)OC(=CC1C(O[Si](C)(C)C)CCCN1[Si](C)(C)C)CN1C=NC2=CC=CC=C2C1=O3527.7Standard polar33892256
(+)-Isofebrifugine,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1CCCNC1CC(=O)CN1C=NC2=CC=CC=C2C1=O3169.6Semi standard non polar33892256
(+)-Isofebrifugine,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1CCCNC1CC(=O)CN1C=NC2=CC=CC=C2C1=O3056.2Standard non polar33892256
(+)-Isofebrifugine,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1CCCNC1CC(=O)CN1C=NC2=CC=CC=C2C1=O3871.1Standard polar33892256
(+)-Isofebrifugine,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC(=CN1C=NC2=CC=CC=C2C1=O)CC1NCCCC1O3298.1Semi standard non polar33892256
(+)-Isofebrifugine,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC(=CN1C=NC2=CC=CC=C2C1=O)CC1NCCCC1O3027.7Standard non polar33892256
(+)-Isofebrifugine,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC(=CN1C=NC2=CC=CC=C2C1=O)CC1NCCCC1O4232.9Standard polar33892256
(+)-Isofebrifugine,1TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC(=CC1NCCCC1O)CN1C=NC2=CC=CC=C2C1=O3285.0Semi standard non polar33892256
(+)-Isofebrifugine,1TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC(=CC1NCCCC1O)CN1C=NC2=CC=CC=C2C1=O3069.4Standard non polar33892256
(+)-Isofebrifugine,1TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC(=CC1NCCCC1O)CN1C=NC2=CC=CC=C2C1=O4127.2Standard polar33892256
(+)-Isofebrifugine,1TBDMS,isomer #4CC(C)(C)[Si](C)(C)N1CCCC(O)C1CC(=O)CN1C=NC2=CC=CC=C2C1=O3219.1Semi standard non polar33892256
(+)-Isofebrifugine,1TBDMS,isomer #4CC(C)(C)[Si](C)(C)N1CCCC(O)C1CC(=O)CN1C=NC2=CC=CC=C2C1=O3106.4Standard non polar33892256
(+)-Isofebrifugine,1TBDMS,isomer #4CC(C)(C)[Si](C)(C)N1CCCC(O)C1CC(=O)CN1C=NC2=CC=CC=C2C1=O4051.3Standard polar33892256
(+)-Isofebrifugine,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=CN1C=NC2=CC=CC=C2C1=O)CC1NCCCC1O[Si](C)(C)C(C)(C)C3479.1Semi standard non polar33892256
(+)-Isofebrifugine,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=CN1C=NC2=CC=CC=C2C1=O)CC1NCCCC1O[Si](C)(C)C(C)(C)C3334.3Standard non polar33892256
(+)-Isofebrifugine,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=CN1C=NC2=CC=CC=C2C1=O)CC1NCCCC1O[Si](C)(C)C(C)(C)C3845.2Standard polar33892256
(+)-Isofebrifugine,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC(=CC1NCCCC1O[Si](C)(C)C(C)(C)C)CN1C=NC2=CC=CC=C2C1=O3475.5Semi standard non polar33892256
(+)-Isofebrifugine,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC(=CC1NCCCC1O[Si](C)(C)C(C)(C)C)CN1C=NC2=CC=CC=C2C1=O3334.0Standard non polar33892256
(+)-Isofebrifugine,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC(=CC1NCCCC1O[Si](C)(C)C(C)(C)C)CN1C=NC2=CC=CC=C2C1=O3761.8Standard polar33892256
(+)-Isofebrifugine,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC1CCCN([Si](C)(C)C(C)(C)C)C1CC(=O)CN1C=NC2=CC=CC=C2C1=O3411.5Semi standard non polar33892256
(+)-Isofebrifugine,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC1CCCN([Si](C)(C)C(C)(C)C)C1CC(=O)CN1C=NC2=CC=CC=C2C1=O3375.9Standard non polar33892256
(+)-Isofebrifugine,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC1CCCN([Si](C)(C)C(C)(C)C)C1CC(=O)CN1C=NC2=CC=CC=C2C1=O3786.2Standard polar33892256
(+)-Isofebrifugine,2TBDMS,isomer #4CC(C)(C)[Si](C)(C)OC(=CN1C=NC2=CC=CC=C2C1=O)CC1C(O)CCCN1[Si](C)(C)C(C)(C)C3491.7Semi standard non polar33892256
(+)-Isofebrifugine,2TBDMS,isomer #4CC(C)(C)[Si](C)(C)OC(=CN1C=NC2=CC=CC=C2C1=O)CC1C(O)CCCN1[Si](C)(C)C(C)(C)C3421.4Standard non polar33892256
(+)-Isofebrifugine,2TBDMS,isomer #4CC(C)(C)[Si](C)(C)OC(=CN1C=NC2=CC=CC=C2C1=O)CC1C(O)CCCN1[Si](C)(C)C(C)(C)C4028.6Standard polar33892256
(+)-Isofebrifugine,2TBDMS,isomer #5CC(C)(C)[Si](C)(C)OC(=CC1C(O)CCCN1[Si](C)(C)C(C)(C)C)CN1C=NC2=CC=CC=C2C1=O3466.2Semi standard non polar33892256
(+)-Isofebrifugine,2TBDMS,isomer #5CC(C)(C)[Si](C)(C)OC(=CC1C(O)CCCN1[Si](C)(C)C(C)(C)C)CN1C=NC2=CC=CC=C2C1=O3396.7Standard non polar33892256
(+)-Isofebrifugine,2TBDMS,isomer #5CC(C)(C)[Si](C)(C)OC(=CC1C(O)CCCN1[Si](C)(C)C(C)(C)C)CN1C=NC2=CC=CC=C2C1=O3963.5Standard polar33892256
(+)-Isofebrifugine,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=CN1C=NC2=CC=CC=C2C1=O)CC1C(O[Si](C)(C)C(C)(C)C)CCCN1[Si](C)(C)C(C)(C)C3702.7Semi standard non polar33892256
(+)-Isofebrifugine,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=CN1C=NC2=CC=CC=C2C1=O)CC1C(O[Si](C)(C)C(C)(C)C)CCCN1[Si](C)(C)C(C)(C)C3618.0Standard non polar33892256
(+)-Isofebrifugine,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=CN1C=NC2=CC=CC=C2C1=O)CC1C(O[Si](C)(C)C(C)(C)C)CCCN1[Si](C)(C)C(C)(C)C3814.7Standard polar33892256
(+)-Isofebrifugine,3TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC(=CC1C(O[Si](C)(C)C(C)(C)C)CCCN1[Si](C)(C)C(C)(C)C)CN1C=NC2=CC=CC=C2C1=O3689.0Semi standard non polar33892256
(+)-Isofebrifugine,3TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC(=CC1C(O[Si](C)(C)C(C)(C)C)CCCN1[Si](C)(C)C(C)(C)C)CN1C=NC2=CC=CC=C2C1=O3595.2Standard non polar33892256
(+)-Isofebrifugine,3TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC(=CC1C(O[Si](C)(C)C(C)(C)C)CCCN1[Si](C)(C)C(C)(C)C)CN1C=NC2=CC=CC=C2C1=O3723.1Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - (+)-Isofebrifugine GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-5910000000-d57051a9a9ddbc220e9e2021-09-23Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (+)-Isofebrifugine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (+)-Isofebrifugine 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 - (+)-Isofebrifugine 10V, Positive-QTOFsplash10-001i-0194000000-77a68c0ee1565ec29dd82021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (+)-Isofebrifugine 20V, Positive-QTOFsplash10-0ul0-0593000000-a307e80e4d1dd6079a7b2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (+)-Isofebrifugine 40V, Positive-QTOFsplash10-001j-9740000000-ddd0a088b9cfe14b51eb2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (+)-Isofebrifugine 10V, Negative-QTOFsplash10-0ue9-0279000000-a3bc72ef92ff8519552b2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (+)-Isofebrifugine 20V, Negative-QTOFsplash10-001j-0590000000-02c2d859a8d5360c6d172021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (+)-Isofebrifugine 40V, Negative-QTOFsplash10-0002-3910000000-d2713516144828cb8be82021-10-12Wishart LabView Spectrum
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 ID103493
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem CompoundNot Available
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 ]