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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2021-09-11 20:19:23 UTC
Update Date2021-09-26 23:15:44 UTC
HMDB IDHMDB0258655
Secondary Accession NumbersNone
Metabolite Identification
Common NameSyrosingopine
DescriptionSyrosingopine belongs to the class of organic compounds known as yohimbine alkaloids. These are alkaloids containing the pentacyclic yohimban skeleton. The Yohimbinoid alkaloids contain a carbocyclic ring E arising through C-17 to C-18 bond formation in a corynantheine precursor. Based on a literature review a significant number of articles have been published on Syrosingopine. This compound has been identified in human blood as reported by (PMID: 31557052 ). Syrosingopine is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Syrosingopine 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
Methyl 17-{4-[(ethoxycarbonyl)oxy]-3,5-dimethoxybenzoyloxy}-6,18-dimethoxy-3,13-diazapentacyclo[11.8.0.0,.0,.0,]henicosa-2(10),4(9),5,7-tetraene-19-carboxylic acidHMDB
Chemical FormulaC35H42N2O11
Average Molecular Weight666.724
Monoisotopic Molecular Weight666.27886018
IUPAC Namemethyl 17-{4-[(ethoxycarbonyl)oxy]-3,5-dimethoxybenzoyloxy}-6,18-dimethoxy-3,13-diazapentacyclo[11.8.0.0^{2,10}.0^{4,9}.0^{15,20}]henicosa-2(10),4(9),5,7-tetraene-19-carboxylate
Traditional Namemethyl 17-{4-[(ethoxycarbonyl)oxy]-3,5-dimethoxybenzoyloxy}-6,18-dimethoxy-3,13-diazapentacyclo[11.8.0.0^{2,10}.0^{4,9}.0^{15,20}]henicosa-2(10),4(9),5,7-tetraene-19-carboxylate
CAS Registry NumberNot Available
SMILES
CCOC(=O)OC1=C(OC)C=C(C=C1OC)C(=O)OC1CC2CN3CCC4=C(NC5=C4C=CC(OC)=C5)C3CC2C(C1OC)C(=O)OC
InChI Identifier
InChI=1S/C35H42N2O11/c1-7-46-35(40)48-31-26(42-3)12-18(13-27(31)43-4)33(38)47-28-14-19-17-37-11-10-22-21-9-8-20(41-2)15-24(21)36-30(22)25(37)16-23(19)29(32(28)44-5)34(39)45-6/h8-9,12-13,15,19,23,25,28-29,32,36H,7,10-11,14,16-17H2,1-6H3
InChI KeyZCDNRPPFBQDQHR-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as yohimbine alkaloids. These are alkaloids containing the pentacyclic yohimban skeleton. The Yohimbinoid alkaloids contain a carbocyclic ring E arising through C-17 to C-18 bond formation in a corynantheine precursor.
KingdomOrganic compounds
Super ClassAlkaloids and derivatives
ClassYohimbine alkaloids
Sub ClassNot Available
Direct ParentYohimbine alkaloids
Alternative Parents
Substituents
  • Yohimbine
  • Corynanthean skeleton
  • Yohimbine alkaloid
  • Beta-carboline
  • Pyridoindole
  • Gallic acid or derivatives
  • M-methoxybenzoic acid or derivatives
  • Benzoate ester
  • M-dimethoxybenzene
  • Dimethoxybenzene
  • 3-alkylindole
  • Indole
  • Indole or derivatives
  • Benzoic acid or derivatives
  • Phenoxy compound
  • Anisole
  • Phenol ether
  • Methoxybenzene
  • Benzoyl
  • Alkyl aryl ether
  • Aralkylamine
  • Piperidine
  • Carbonic acid diester
  • Monocyclic benzene moiety
  • Dicarboxylic acid or derivatives
  • Benzenoid
  • Pyrrole
  • Heteroaromatic compound
  • Methyl ester
  • Tertiary amine
  • Carboxylic acid ester
  • Carbonic acid derivative
  • Tertiary aliphatic amine
  • Amino acid or derivatives
  • Azacycle
  • Organoheterocyclic compound
  • Carboxylic acid derivative
  • Ether
  • Dialkyl ether
  • Organooxygen compound
  • Amine
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organonitrogen compound
  • Carbonyl group
  • Organic oxygen compound
  • Organopnictogen compound
  • 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
logP4.39ALOGPS
logP4.27ChemAxon
logS-4.8ALOGPS
pKa (Strongest Acidic)16.29ChemAxon
pKa (Strongest Basic)7.39ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count9ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area144.08 ŲChemAxon
Rotatable Bond Count13ChemAxon
Refractivity172.46 m³·mol⁻¹ChemAxon
Polarizability72.37 ųChemAxon
Number of Rings6ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+247.40930932474
DeepCCS[M-H]-245.51330932474
DeepCCS[M-2H]-278.75430932474
DeepCCS[M+Na]+253.19630932474
AllCCS[M+H]+252.032859911
AllCCS[M+H-H2O]+251.232859911
AllCCS[M+NH4]+252.832859911
AllCCS[M+Na]+253.032859911
AllCCS[M-H]-245.132859911
AllCCS[M+Na-2H]-248.432859911
AllCCS[M+HCOO]-252.232859911

Predicted Retention Times

Underivatized

Chromatographic MethodRetention TimeReference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.6.54 minutes32390414
Predicted by Siyang on May 30, 202215.0541 minutes33406817
Predicted by Siyang using ReTip algorithm on June 8, 20222.63 minutes32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid3287.7 seconds40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid178.2 seconds40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid244.2 seconds40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid169.8 seconds40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid141.7 seconds40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid695.3 seconds40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid607.2 seconds40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)424.5 seconds40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid1213.8 seconds40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid633.7 seconds40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid2019.7 seconds40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid419.9 seconds40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid452.7 seconds40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate283.4 seconds40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA178.1 seconds40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water12.3 seconds40023050

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
SyrosingopineCCOC(=O)OC1=C(OC)C=C(C=C1OC)C(=O)OC1CC2CN3CCC4=C(NC5=C4C=CC(OC)=C5)C3CC2C(C1OC)C(=O)OC5705.2Standard polar33892256
SyrosingopineCCOC(=O)OC1=C(OC)C=C(C=C1OC)C(=O)OC1CC2CN3CCC4=C(NC5=C4C=CC(OC)=C5)C3CC2C(C1OC)C(=O)OC4809.1Standard non polar33892256
SyrosingopineCCOC(=O)OC1=C(OC)C=C(C=C1OC)C(=O)OC1CC2CN3CCC4=C(NC5=C4C=CC(OC)=C5)C3CC2C(C1OC)C(=O)OC5067.2Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Syrosingopine,1TMS,isomer #1CCOC(=O)OC1=C(OC)C=C(C(=O)OC2CC3CN4CCC5=C(C4CC3C(C(=O)OC)C2OC)N([Si](C)(C)C)C2=CC(OC)=CC=C52)C=C1OC4956.9Semi standard non polar33892256
Syrosingopine,1TMS,isomer #1CCOC(=O)OC1=C(OC)C=C(C(=O)OC2CC3CN4CCC5=C(C4CC3C(C(=O)OC)C2OC)N([Si](C)(C)C)C2=CC(OC)=CC=C52)C=C1OC4553.5Standard non polar33892256
Syrosingopine,1TMS,isomer #1CCOC(=O)OC1=C(OC)C=C(C(=O)OC2CC3CN4CCC5=C(C4CC3C(C(=O)OC)C2OC)N([Si](C)(C)C)C2=CC(OC)=CC=C52)C=C1OC6781.9Standard polar33892256
Syrosingopine,1TBDMS,isomer #1CCOC(=O)OC1=C(OC)C=C(C(=O)OC2CC3CN4CCC5=C(C4CC3C(C(=O)OC)C2OC)N([Si](C)(C)C(C)(C)C)C2=CC(OC)=CC=C52)C=C1OC5063.7Semi standard non polar33892256
Syrosingopine,1TBDMS,isomer #1CCOC(=O)OC1=C(OC)C=C(C(=O)OC2CC3CN4CCC5=C(C4CC3C(C(=O)OC)C2OC)N([Si](C)(C)C(C)(C)C)C2=CC(OC)=CC=C52)C=C1OC4676.3Standard non polar33892256
Syrosingopine,1TBDMS,isomer #1CCOC(=O)OC1=C(OC)C=C(C(=O)OC2CC3CN4CCC5=C(C4CC3C(C(=O)OC)C2OC)N([Si](C)(C)C(C)(C)C)C2=CC(OC)=CC=C52)C=C1OC6737.2Standard polar33892256
Spectra

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Syrosingopine 6V, Negative-QTOFsplash10-014i-0010019000-7fcde86a9944ec40fa602021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Syrosingopine 6V, Positive-QTOFsplash10-014i-0000009000-94be94a76eac46eadbd62021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Syrosingopine 6V, Positive-QTOFsplash10-004i-0891000000-bd01e1654c8d6b6c06f72021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Syrosingopine 6V, Positive-QTOFsplash10-014i-0000009000-9cb2af563f1a3b63f2cc2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Syrosingopine 6V, Positive-QTOFsplash10-00e9-0920000000-3e71f9d81714ecd653d52021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Syrosingopine 6V, Positive-QTOFsplash10-014i-0000009000-ad63bcfc9f6a53d46deb2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Syrosingopine 6V, Positive-QTOFsplash10-014i-0101009000-08a683d9f7694d308b872021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Syrosingopine 6V, Positive-QTOFsplash10-014i-0010019000-96e4c968017538bfeeb12021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Syrosingopine 6V, Positive-QTOFsplash10-014j-0428149000-043b11fe6e71f47b7e2f2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Syrosingopine 6V, Positive-QTOFsplash10-014i-0000009000-7b8fcc8bc8f0a15f651c2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Syrosingopine 6V, Positive-QTOFsplash10-014l-0571097000-345a4298db27ac9608142021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Syrosingopine 6V, Positive-QTOFsplash10-014l-0561098000-22364e96cec7c2ca45df2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Syrosingopine 6V, Positive-QTOFsplash10-014i-0000009000-a8575e8d3d75592e59e32021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Syrosingopine 6V, Positive-QTOFsplash10-0fr6-0461096000-6fd2915804ae3ccd6d452021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Syrosingopine 6V, Positive-QTOFsplash10-014i-0000009000-d47079b17a2086c867f52021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Syrosingopine 6V, Positive-QTOFsplash10-014i-0000009000-c2b599badcc44eb575922021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Syrosingopine 6V, Positive-QTOFsplash10-014j-0327149000-be073b2ea45030a3bbfe2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Syrosingopine 6V, Positive-QTOFsplash10-014i-0101009000-d9d371e8401c3714e8e32021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Syrosingopine 6V, Positive-QTOFsplash10-004i-0591000000-6bffe3f305092fe139052021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Syrosingopine 6V, Positive-QTOFsplash10-014i-0100019000-8fdd61b01e56d31d9e572021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Syrosingopine 6V, Positive-QTOFsplash10-00e9-0910000000-6d819b182ab053ff366a2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Syrosingopine 6V, Positive-QTOFsplash10-014j-0428149000-77afccdf556a6aee84c02021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Syrosingopine 6V, Positive-QTOFsplash10-004i-0691000000-2b9734bc04e33b22f0f52021-09-20HMDB team, MONAView 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 ID5174
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkSyrosingopine
METLIN IDNot Available
PubChem Compound5367
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 ]