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Showing Compound Capsianside A (FDB012286)

Record Information
Version1.0
Creation date2010-04-08 22:10:05 UTC
Update date2019-11-26 03:06:31 UTC
Primary IDFDB012286
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameCapsianside A
DescriptionCapsianside A belongs to the class of organic compounds known as sophorolipids. These are glycolipids containing a sophorose moiety linked glycosidically to the hydroxyl group of a 17-hydroxy-C18 saturated fatty acid. The carboxyl group of the fatty acid can be linked to the 4'-hydroxyl of the second glucose to form a lactone. Based on a literature review a significant number of articles have been published on Capsianside A.
CAS Number116107-40-5
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
2-({6-[(2-{[(2E,6Z,10E)-14-{[4,5-dihydroxy-6-(hydroxymethyl)-3-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-2,6,10,14-tetramethylhexadeca-2,6,10,15-tetraen-1-yl]oxy}-3,5-dihydroxy-6-methyloxan-4-yl)oxy]-3,4,5-trihydroxyoxan-2-yl}methoxy)-4,5-dihydroxy-6-methyloxan-3-yl (2Z,6Z,10Z)-4-hydroxy-2,6,10,14-tetramethyl-14-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}hexadeca-2,6,10,15-tetraenoic acidHMDB
Capsianside Adb_source
Predicted Properties
PropertyValueSource
Water Solubility0.084 g/LALOGPS
logP1.58ALOGPS
logP0.98ChemAxon
logS-4.3ALOGPS
pKa (Strongest Acidic)11.67ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count32ChemAxon
Hydrogen Donor Count19ChemAxon
Polar Surface Area521.43 ŲChemAxon
Rotatable Bond Count40ChemAxon
Refractivity388.53 m³·mol⁻¹ChemAxon
Polarizability163.92 ųChemAxon
Number of Rings6ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC76H124O33
IUPAC name2-({6-[(2-{[(2E,6Z,10E)-14-{[4,5-dihydroxy-6-(hydroxymethyl)-3-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-2,6,10,14-tetramethylhexadeca-2,6,10,15-tetraen-1-yl]oxy}-3,5-dihydroxy-6-methyloxan-4-yl)oxy]-3,4,5-trihydroxyoxan-2-yl}methoxy)-4,5-dihydroxy-6-methyloxan-3-yl (2Z,6Z,10Z)-4-hydroxy-2,6,10,14-tetramethyl-14-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}hexadeca-2,6,10,15-tetraenoate
InChI IdentifierInChI=1S/C76H124O33/c1-13-75(11,108-72-63(94)57(88)53(84)47(33-78)102-72)28-18-26-39(5)22-16-24-40(6)30-45(80)31-42(8)68(96)105-66-59(90)50(81)43(9)100-73(66)98-36-49-55(86)58(89)62(93)71(104-49)106-65-51(82)44(10)99-69(64(65)95)97-35-41(7)25-17-23-37(3)20-15-21-38(4)27-19-29-76(12,14-2)109-74-67(60(91)54(85)48(34-79)103-74)107-70-61(92)56(87)52(83)46(32-77)101-70/h13-14,20,24-27,31,43-67,69-74,77-95H,1-2,15-19,21-23,28-30,32-36H2,3-12H3/b37-20-,38-27+,39-26-,40-24-,41-25+,42-31-
InChI KeyKUPGGXGLYVOMMG-UOSNZFRRSA-N
Isomeric SMILESCC1OC(OCC2OC(OC3C(O)C(C)OC(OC\C(C)=C\CC\C(C)=C/CC\C(C)=C\CCC(C)(OC4OC(CO)C(O)C(O)C4OC4OC(CO)C(O)C(O)C4O)C=C)C3O)C(O)C(O)C2O)C(OC(=O)C(\C)=C/C(O)C\C(C)=C/CC\C(C)=C/CCC(C)(OC2OC(CO)C(O)C(O)C2O)C=C)C(O)C1O
Average Molecular Weight1565.778
Monoisotopic Molecular Weight1564.802486494
Classification
Description Belongs to the class of organic compounds known as sophorolipids. These are glycolipids containing a sophorose moiety linked glycosidically to the hydroxyl group of a 17-hydroxy-C18 saturated fatty acid. The carboxyl group of the fatty acid can be linked to the 4'-hydroxyl of the second glucose to form a lactone.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acyl glycosides
Direct ParentSophorolipids
Alternative Parents
Substituents
  • Sophorolipid
  • Diterpene glycoside
  • Oligosaccharide
  • Diterpenoid
  • Terpene glycoside
  • Long chain fatty alcohol
  • Alkyl glycoside
  • Glycosyl compound
  • O-glycosyl compound
  • Fatty alcohol
  • Fatty acid ester
  • Oxane
  • Alpha,beta-unsaturated carboxylic ester
  • Enoate ester
  • Carboxylic acid ester
  • Secondary alcohol
  • Oxacycle
  • Carboxylic acid derivative
  • Organoheterocyclic compound
  • Polyol
  • Acetal
  • Monocarboxylic acid or derivatives
  • Organic oxygen compound
  • Organic oxide
  • Primary alcohol
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 58.30%; H 7.98%; O 33.72%DFC
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]D -25.1 (MeOH)DFC
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MSNot Available
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000b-1165492301-a7456c98b722814749292017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0h51-3195847500-125790d7679ddbfee3062017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ims-3383956300-8295c471a19fb32db4022017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0032-3345694202-93c9fcb7229c9a4c6d4c2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-002b-1634961211-741d5b64c787d0d09dfc2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-002b-3612902000-9bd2bf6ccc7023882d8f2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0400-0400692308-57dcdcd1ff41ebe62e062021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03fr-5402920202-8a58ce2efda5e7c6b02c2021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-02dm-0801829201-b4edcc22f06ee4b8fcfc2021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-05mo-9137321502-c3914f97e178ca326a202021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-006x-9443231102-97ba564be33e58be7ec32021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00kr-4934442106-fc41aae914b548311ac92021-09-24View Spectrum
NMRNot Available
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound IDNot Available
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB34044
CRC / DFC (Dictionary of Food Compounds) IDHFQ21-O:HFQ21-O
EAFUS IDNot Available
Dr. Duke IDCAPSIANSIDE-A|CAPSIANOSIDE-A
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
Angiotensin converting enzyme inhibitor35457 An agent that blocks the conversion of angiotensin I to angiotensin II, reducing blood pressure and fluid retention. Therapeutically, it's used to treat hypertension, heart failure, and protect kidney function in diabetes, thereby reducing the risk of cardiovascular disease and stroke.DUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).