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Record Information
Version2.0
Created at2022-04-28 17:09:51 UTC
Updated at2022-04-28 17:09:51 UTC
NP-MRD IDNP0071815
Secondary Accession NumbersNone
Natural Product Identification
Common NameScillascillin
DescriptionScillascillin belongs to the class of organic compounds known as isoflavanones. These are polycyclic compounds containing an isoflavan skeleton which bears a ketone at position C4. Scillascillin is found in Merwilla plumbea, Muscari neglectum and Scilla scilloides DRUCE. Scillascillin was first documented in 2004 (PMID: 15165167). Based on a literature review a small amount of articles have been published on Scillascillin (PMID: 25612441) (PMID: 25632469) (PMID: 25276067) (PMID: 25153098).
Structure
Thumb
SynonymsNot Available
Chemical FormulaC17H12O6
Average Mass312.2770 Da
Monoisotopic Mass312.06339 Da
IUPAC Name(3R)-5,7-dihydroxy-2,4-dihydro-9',11'-dioxaspiro[1-benzopyran-3,4'-tricyclo[6.3.0.0^{3,6}]undecane]-1',3'(6'),7'-trien-4-one
Traditional Name(3R)-5,7-dihydroxy-2H-9',11'-dioxaspiro[1-benzopyran-3,4'-tricyclo[6.3.0.0^{3,6}]undecane]-1',3'(6'),7'-trien-4-one
CAS Registry NumberNot Available
SMILES
OC1=CC(O)=C2C(=O)[C@@]3(CC4=C3C=C3OCOC3=C4)COC2=C1
InChI Identifier
InChI=1S/C17H12O6/c18-9-2-11(19)15-14(3-9)21-6-17(16(15)20)5-8-1-12-13(4-10(8)17)23-7-22-12/h1-4,18-19H,5-7H2/t17-/m0/s1
InChI KeySAXOGBBWXWKZKR-KRWDZBQOSA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Merwilla plumbeaLOTUS Database
Muscari neglectumLOTUS Database
Scilla scilloides DRUCEPlant
Chemical Taxonomy
Description Belongs to the class of organic compounds known as isoflavanones. These are polycyclic compounds containing an isoflavan skeleton which bears a ketone at position C4.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassIsoflavonoids
Sub ClassIsoflavans
Direct ParentIsoflavanones
Alternative Parents
Substituents
  • Isoflavanol
  • Isoflavanone
  • Chromone
  • Chromane
  • Benzopyran
  • 1-benzopyran
  • Benzodioxole
  • Aryl alkyl ketone
  • Aryl ketone
  • Alkyl aryl ether
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Benzenoid
  • Vinylogous acid
  • Ketone
  • Oxacycle
  • Organoheterocyclic compound
  • Acetal
  • Ether
  • Organic oxide
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP2.27ALOGPS
logP2.82ChemAxon
logS-3.1ALOGPS
pKa (Strongest Acidic)7.84ChemAxon
pKa (Strongest Basic)-4.5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area85.22 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity78.6 m³·mol⁻¹ChemAxon
Polarizability31.31 ųChemAxon
Number of Rings5ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDC00031319
Chemspider ID28425464
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound75492722
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Wang YM, Fan MY, Li J, Wang ZM, Gao HM: [Homoisoflavanones and stilbenes from fresh bulb of Scilla scilloides]. Zhongguo Zhong Yao Za Zhi. 2014 Oct;39(19):3788-93. [PubMed:25612441 ]
  2. Moodley N, Mulholland DA, Crouch NR: Eucosterol-type nortriterpenoids from Merwilla natalensis. J Nat Prod. 2004 May;67(5):918-20. doi: 10.1021/np0204803. [PubMed:15165167 ]
  3. Matsuo Y, Kurihara R, Akagi N, Mimaki Y: Two new homoisoflavonoids from the bulbs of Bessera elegans. Nat Prod Commun. 2014 Dec;9(12):1725-7. [PubMed:25632469 ]
  4. Chinthala Y, Chinde S, Kumar AN, Srinivas KV, Kumar JK, Sastry KP, Grover P, Ramana MV: Anticancer Active Homoisoflavone from the Underground Bulbs of Ledebouria hyderabadensis. Pharmacognosy Res. 2014 Oct;6(4):303-5. doi: 10.4103/0974-8490.138272. [PubMed:25276067 ]
  5. Lin LG, Liu QY, Ye Y: Naturally occurring homoisoflavonoids and their pharmacological activities. Planta Med. 2014 Aug;80(13):1053-66. doi: 10.1055/s-0034-1383026. Epub 2014 Aug 25. [PubMed:25153098 ]