Cucurbitacin B (CED0006678)

Record Information
Version1.0
Creation Date2016-05-26 00:46:25 UTC
Update Date2026-08-22 11:00:37 UTC
Accession NumberCHEM028884
Identification
Common NameCucurbitacin B
ClassSmall Molecule
Description
Cucurbitacin B belongs to the cucurbitacins, a subclass of steroids and steroid derivatives within the organic compounds. With an average molecular weight of 558.70 g/mol, Cucurbitacin B is a heavy molecule. It is characterized by the chemical formula C32H46O8 and is classified within the superclass of lipids and lipid-like molecules. In industrial applications, this compound serves as a softener and conditioner. It has been identified in 14 recorded sources across several sectors. Within the electrical and electronic equipment sector, it is found in cell phones, capacitors, wires and cables, batteries, and printed circuit boards, among one other source. Its presence is also noted in the food, food processing and cookware sector, specifically in food packaging and the preparation of vinegar. In the textiles, leather and furnishings sector, it is associated with carpets, rugs, and synthetic textiles. Additionally, it is found in medical devices within the healthcare, pharmaceuticals and veterinary products sector. In the energy, oil and gas sector, as well as in industrial manufacturing and chemical processing, it is used in lubricants. It is also found in one other sector. Recorded routes of exposure for Cucurbitacin B include inhalation, oral ingestion, and touch.
Contaminant Type
  • PFAS
  • Phytotoxin
Chemical Structure
Synonyms
ValueSource
Amarin?HMDB
Cucurbitacine (b)HMDB
Datisca principle bHMDB
Datiscn principle bHMDB
(3E)-6-{4,13-dihydroxy-1,6,6,11,15-pentamethyl-5,17-dioxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-14-yl}-6-hydroxy-2-methyl-5-oxohept-3-en-2-yl acetic acidGenerator
Chemical FormulaC32H46O8
Average Molecular Mass558.703 g/mol
Monoisotopic Mass558.319 g/mol
CAS Registry Number6199-67-3
IUPAC Name(3E)-6-{4,13-dihydroxy-1,6,6,11,15-pentamethyl-5,17-dioxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-14-yl}-6-hydroxy-2-methyl-5-oxohept-3-en-2-yl acetate
Traditional Namecucurbitacin B
SMILESCC(=O)OC(C)(C)\C=C\C(=O)C(C)(O)C1C(O)CC2(C)C3CC=C4C(CC(O)C(=O)C4(C)C)C3(C)C(=O)CC12C
InChI IdentifierInChI=1S/C32H46O8/c1-17(33)40-27(2,3)13-12-23(36)32(9,39)25-21(35)15-29(6)22-11-10-18-19(14-20(34)26(38)28(18,4)5)31(22,8)24(37)16-30(25,29)7/h10,12-13,19-22,25,34-35,39H,11,14-16H2,1-9H3/b13-12+
InChI KeyIXQKXEUSCPEQRD-OUKQBFOZSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as cucurbitacins. These are polycyclic compounds containing the tetracyclic cucurbitane nucleus skeleton, 19-(10->9b)-abeo-10alanost-5-ene (also known as 9b-methyl-19-nor lanosta-5-ene), with a variety of oxygenation functionalities at different positions.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassCucurbitacins
Direct ParentCucurbitacins
Alternative Parents
Substituents
  • Cucurbitacin skeleton
  • Triterpenoid
  • 22-oxosteroid
  • 21-oxosteroid
  • 20-hydroxysteroid
  • Steroid ester
  • 3-oxo-delta-5-steroid
  • 2-hydroxysteroid
  • Hydroxysteroid
  • 3-oxosteroid
  • 11-oxosteroid
  • Oxosteroid
  • 16-hydroxysteroid
  • Delta-5-steroid
  • Acyloin
  • Acryloyl-group
  • Alpha,beta-unsaturated ketone
  • Cyclic alcohol
  • Alpha-hydroxy ketone
  • Tertiary alcohol
  • Enone
  • Cyclic ketone
  • Secondary alcohol
  • Carboxylic acid ester
  • Ketone
  • Carboxylic acid derivative
  • Monocarboxylic acid or derivatives
  • Carbonyl group
  • Organic oxide
  • Alcohol
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organic oxygen compound
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External DescriptorsNot Available
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Organoleptic EffectsNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.0056 g/LALOGPS
logP3.7ALOGPS
logP3.13ChemAxon
logS-5ALOGPS
pKa (Strongest Acidic)12.8ChemAxon
pKa (Strongest Basic)-2.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area138.2 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity151.04 m³·mol⁻¹ChemAxon
Polarizability60.69 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrumsplash10-0gvn-2204590000-999244d691afface476fNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS Spectrumsplash10-01b9-3102195000-67590cd44207aca4c298Not AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
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Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
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Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
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Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
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Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-052f-0002490000-340cd111be87d04d2109Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-000w-1304920000-962e19bce41b3a8d95b9Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-000l-2129410000-7ddb916021a8e5112d5aNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a4j-3900380000-17ed96fef5434e9fdd14Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a4j-5903120000-0a58b6b4a29153fefb70Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a4i-9105300000-aed0a8da08a2f614aaccNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0002-0000910000-2fb757c84672eba50afaNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a4i-9000000000-adc51a9625e7766250c5Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a4v-4001900000-b913bef2cb75f8c0debcNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-000t-0100910000-d57bb7e6e5b6c7259024Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-000e-9501410000-a5aebb06a3552f6953f0Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-014l-9612300000-18db14fe4f5cfcf5b1faNot AvailableView Spectrum
Toxicity Profile
Mechanism of ToxicityNot Available
Carcinogenicity (IARC Classification)Not Available
Minimum Risk LevelNot Available
SymptomsNot Available
TreatmentNot Available
Toxicity Values
Toxicity ValueUnitValue RangeOrganismDose DescriptorRoute of ExposurePredicted or ExperimentalReference
2380.0Log mg/kg[1300:4200]RatLD50oralpredictedNot Available
Health Effects
Health EffectRelationshipDirectionReference
Exposure Sources
Source IDSourceSectorReference
7PesticidesAgriculture & land managementNot Available
120Wires and cablesElectrical & Electronic EquipmentNot Available
121Printed circuit boardsElectrical & Electronic EquipmentNot Available
125BatteriesElectrical & Electronic EquipmentNot Available
130SemiconductorsElectrical & Electronic EquipmentNot Available
138LubricantsEnergy, oil & gasNot Available
147Food packagingFood, food processing & cookwareNot Available
174LubricantsIndustrial manufacturing & chemical processingNot Available
234Medical devicesHealthcare, pharmaceuticals & veterinary productsNot Available
451Carpets and RugsTextiles, leather & furnishingsNot Available
454Synthetic textilesTextiles, leather & furnishingsNot Available
490Personal care & cosmeticsNot Available
492Cell phonesElectrical & Electronic EquipmentNot Available
493CapacitorsElectrical & Electronic EquipmentNot Available
548Preparation Of VinegarFood, food processing & cookwareNot Available
583Anchoring EquipmentMarine, shipping & aquacultureNot Available
589Life BuoysMarine, shipping & aquacultureNot Available
592Marine Propulsion Or SteeringMarine, shipping & aquacultureNot Available
593Nautical InstrumentsMarine, shipping & aquacultureNot Available
594Ship HullsMarine, shipping & aquacultureNot Available
Pathways
0 pathways

No pathways found

No metabolic pathways have been associated with this synthetic chemical

Targets
StructureProteinUniProt IDOrganismRelationshipDetails
Signal transducer and activator of transcription 3 structureClick to view 3D structureSignal transducer and activator of transcription 3P40763HumansPredicted (SEA)10.0426
Hypoxia-inducible factor 1-alpha structureClick to view 3D structureHypoxia-inducible factor 1-alphaQ16665HumansPredicted (SEA)0.544945
Integrin alpha-L structureClick to view 3D structureIntegrin alpha-LP20701HumansPredicted (SEA)0.233548
Insulin-like growth factor 2 mRNA-binding protein 1 structureClick to view 3D structureInsulin-like growth factor 2 mRNA-binding protein 1Q9NZI8HumansPredicted (SEA)11.2881
Tyrosine-protein phosphatase non-receptor type 1 structureClick to view 3D structureTyrosine-protein phosphatase non-receptor type 1P18031HumansPredicted (SEA)1279.22
Click to view 3D structureTransient receptor potential cation channel subfamily M member 2E9PTA2Rattus norvegicusPredicted (SEA)5.44945
FUN14 domain-containing protein 1 structureClick to view 3D structureFUN14 domain-containing protein 1Q8IVP5HumansPredicted (SEA)7.31783
G-protein coupled bile acid receptor 1 structureClick to view 3D structureG-protein coupled bile acid receptor 1Q8TDU6HumansPredicted (SEA)544.088
Tyrosine-protein phosphatase non-receptor type 2 structureClick to view 3D structureTyrosine-protein phosphatase non-receptor type 2P17706HumansPredicted (SEA)795.463
Click to view 3D structureGlycogen [starch] synthase, liverP54840HumansPredicted (SEA)18.1389
Click to view 3D structureGlucose-6-phosphatase catalytic subunit 1P43428Rattus norvegicusPredicted (SEA)18.1389
Aldo-keto reductase family 1 member B10 structureClick to view 3D structureAldo-keto reductase family 1 member B10O60218HumansPredicted (SEA)843.886
Tissue factor structureClick to view 3D structureTissue factorP13726HumansPredicted (SEA)647.706
Bile acid receptor structureClick to view 3D structureBile acid receptorQ96RI1HumansPredicted (SEA)3103.85
Click to view 3D structureProteaseQ9YQ12Human immunodeficiency virus 1Predicted (SEA)766.503
Click to view 3D structureEcdysone receptorP34021Drosophila melanogasterPredicted (SEA)14.0907
Glucocorticoid receptor structureClick to view 3D structureGlucocorticoid receptorP04150HumansPredicted (SEA)3829.4
Click to view 3D structureStreptokinase AP10520Streptococcus pyogenes serotype M1Predicted (SEA)5955.39
Androgen receptor structureClick to view 3D structureAndrogen receptorP10275HumansPredicted (SEA)4110.59
11-beta-hydroxysteroid dehydrogenase 1 structureClick to view 3D structure11-beta-hydroxysteroid dehydrogenase 1P28845HumansPredicted (SEA)2720.67
Click to view 3D structureAcetylcholinesteraseO42275Electrophorus electricusPredicted (SEA)5072.58
Sex hormone-binding globulin structureClick to view 3D structureSex hormone-binding globulinP04278HumansPredicted (SEA)130.631
Click to view 3D structureAndrogen receptorP15207Rattus norvegicusPredicted (SEA)1384.16
Click to view 3D structureProgesterone receptorQ690N0Bos taurusPredicted (SEA)280.102
Progesterone receptor structureClick to view 3D structureProgesterone receptorP06401HumansPredicted (SEA)5042.22
Concentrations
Not Available
External Links
DrugBank IDNot Available
HMDB IDHMDB0034927
FooDB IDFDB013515
Phenol Explorer IDNot Available
KNApSAcK IDC00003683
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkCucurbitacin
Chemspider ID4510124
ChEBI IDNot Available
PubChem Compound ID5353545
Kegg Compound IDC08794
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9.
2. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10.
3. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20.
4. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621.
5. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.
6. The lipid handbook with CD-ROM