Np mrd loader

Showing NP-Card for Tulipalin A (NP0077320)

Jump To Section:
IdentificationSpectraBioTaxonomyChemoTaxonomyPhysical propertiesLinksReferencesXML
Record Information
Version2.0
Created at2022-04-28 22:29:10 UTC
Updated at2022-04-28 22:29:10 UTC
NP-MRD IDNP0077320
Secondary Accession NumbersNone
Natural Product Identification
Common NameTulipalin A
DescriptionAlpha-methylene gamma-butyrolactone, also known as tulipalin a or 3-methylenedihydro-2(3H)-furanone, belongs to the class of organic compounds known as gamma butyrolactones. Gamma butyrolactones are compounds containing a gamma butyrolactone moiety, which consists of an aliphatic five-member ring with four carbon atoms, one oxygen atom, and bears a ketone group on the carbon adjacent to the oxygen atom. Alpha-methylene gamma-butyrolactone is an extremely weak basic (essentially neutral) compound (based on its pKa). Tulipalin A is found in Alstroemeria angustifolia, Alstroemeria pallida, Erythronium americanum, Erythronium grandiflorum, Fritillaria imperialis , Fritillaria meleagris, Laurus nobilis, Spiraea thunbergii, Tulipa clusiana, Tulipa gesneriana and Tulipa turkestanica. Tulipalin A was first documented in 1984 (PMID: 6476889). A butan-4-olide having a methylene group at the 3-position.
Structure
Thumb
MOL3D MOLSDFPDBSMILESInChI

MOL for NP0077320 (Tulipalin A)


  Mrv1533004161514452D          

  7  7  0  0  0  0            999 V2000
    0.5678    1.9393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    1.1143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2352    0.6294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9803   -0.1553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1553   -0.1553    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0997    0.6294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8843    0.8843    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  2  6  1  0  0  0  0
  6  7  2  0  0  0  0
M  END
Download

3D MOL for NP0077320 (Tulipalin A)

     RDKit          3D

 13 13  0  0  0  0  0  0  0  0999 V2000
    1.8427   -0.1157    0.6327 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6721    0.1109    0.0907 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3081   -0.9152   -0.4080 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6125   -0.1446   -0.1706 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2580    1.1309   -0.6720 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0177    1.3916   -0.1698 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5563    2.5159    0.0403 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1882   -1.1185    0.7582 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4499    0.7017    0.9484 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1244   -1.0713   -1.4843 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2425   -1.8178    0.2066 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7205   -0.0660    0.9194 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4610   -0.6019   -0.6915 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  6  2  1  0
  1  8  1  0
  1  9  1  0
  3 10  1  0
  3 11  1  0
  4 12  1  0
  4 13  1  0
M  END
Download

3D SDF for NP0077320 (Tulipalin A)


  Mrv1533004161514452D          

  7  7  0  0  0  0            999 V2000
    0.5678    1.9393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    1.1143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2352    0.6294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9803   -0.1553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1553   -0.1553    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0997    0.6294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8843    0.8843    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  2  6  1  0  0  0  0
  6  7  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0077320

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C=C1CCOC1=O

> <INCHI_IDENTIFIER>
InChI=1S/C5H6O2/c1-4-2-3-7-5(4)6/h1-3H2

> <INCHI_KEY>
GSLDEZOOOSBFGP-UHFFFAOYSA-N

> <FORMULA>
C5H6O2

> <MOLECULAR_WEIGHT>
98.101

> <EXACT_MASS>
98.036779433

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
13

> <JCHEM_AVERAGE_POLARIZABILITY>
9.421352634592743

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-methylideneoxolan-2-one

> <ALOGPS_LOGP>
0.39

> <JCHEM_LOGP>
0.8341922883333334

> <ALOGPS_LOGS>
0.06

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-6.847029159484089

> <JCHEM_POLAR_SURFACE_AREA>
26.3

> <JCHEM_REFRACTIVITY>
24.686

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.13e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
tulipalin A

> <JCHEM_VEBER_RULE>
1

$$$$
Download

3D-SDF for NP0077320 (Tulipalin A)

Download
PDB for NP0077320 (Tulipalin A)
HEADER    PROTEIN                                 16-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   16-APR-15         0                                  
HETATM    1  C   UNK     0       1.060   3.620   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.060   2.080   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.306   1.175   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.830  -0.290   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       0.290  -0.290   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      -0.186   1.175   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -1.651   1.651   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    6                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    2    7                                                  
CONECT    7    6                                                            
MASTER        0    0    0    0    0    0    0    0    7    0   14    0
END

Download
3D PDB for NP0077320 (Tulipalin A)
Download
SMILES for NP0077320 (Tulipalin A)
C=C1CCOC1=O
Download
INCHI for NP0077320 (Tulipalin A)
InChI=1S/C5H6O2/c1-4-2-3-7-5(4)6/h1-3H2
Download
View in JSmol
Synonyms
ValueSource
3-Methylenedihydro-2(3H)-furanoneChEBI
alpha-Methylene butyrolactoneChEBI
alpha-Methylene-gamma-butyrolactoneChEBI
alpha-Methylidene-gamma-butyrolactoneChEBI
Dihydro-3-methylene-2(3H)-furanoneChEBI
Tulipalin aChEBI
2-MethylenebutanolactoneKegg
a-Methylene butyrolactoneGenerator
Α-methylene butyrolactoneGenerator
a-Methylene-g-butyrolactoneGenerator
Α-methylene-γ-butyrolactoneGenerator
a-Methylidene-g-butyrolactoneGenerator
Α-methylidene-γ-butyrolactoneGenerator
a-Methylene g-butyrolactoneGenerator
Α-methylene γ-butyrolactoneGenerator
alpha-Methylene gamma-butyrolactoneMeSH
Chemical FormulaC5H6O2
Average Mass98.1010 Da
Monoisotopic Mass98.03678 Da
IUPAC Name3-methylideneoxolan-2-one
Traditional Nametulipalin A
CAS Registry NumberNot Available
SMILES
C=C1CCOC1=O
InChI Identifier
InChI=1S/C5H6O2/c1-4-2-3-7-5(4)6/h1-3H2
InChI KeyGSLDEZOOOSBFGP-UHFFFAOYSA-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
Alstroemeria angustifoliaLOTUS Database
Alstroemeria pallidaLOTUS Database
Erythronium americanumLOTUS Database
Erythronium grandiflorumLOTUS Database
Fritillaria imperialisPlant
Fritillaria meleagrisPlant
Laurus nobilisLOTUS Database
Spiraea thunbergiiLOTUS Database
Tulipa clusianaLOTUS Database
Tulipa gesnerianaLOTUS Database
Tulipa turkestanicaPlant
Chemical Taxonomy
Description Belongs to the class of organic compounds known as gamma butyrolactones. Gamma butyrolactones are compounds containing a gamma butyrolactone moiety, which consists of an aliphatic five-member ring with four carbon atoms, one oxygen atom, and bears a ketone group on the carbon adjacent to the oxygen atom.
KingdomOrganic compounds  
Super ClassOrganoheterocyclic compounds  
ClassLactones  
Sub ClassGamma butyrolactones  
Direct ParentGamma butyrolactones  
Alternative Parents
Substituents
  • Gamma butyrolactone
    • 

  • Alpha,beta-unsaturated carboxylic ester
    • 

  • Enoate ester
    • 

  • Tetrahydrofuran
    • 

  • Carboxylic acid ester
    • 

  • Oxacycle
    • 

  • Monocarboxylic acid or derivatives
    • 

  • Carboxylic acid derivative
    • 

  • Organic oxygen compound
    • 

  • Organic oxide
    • 

  • Hydrocarbon derivative
    • 

  • Organooxygen compound
    • 

  • Carbonyl group
    • 

  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
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
logP0.39ALOGPS
logP0.83ChemAxon
logS0.06ALOGPS
pKa (Strongest Basic)-6.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area26.3 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity24.69 m³·mol⁻¹ChemAxon
Polarizability9.42 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDC20578  
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound68352  
PDB IDNot Available
ChEBI ID104120  
Good Scents IDNot Available
References
General References
  1. Cheminat A, Stampf JL, Benezra C: Allergic contact dermatitis to laurel (Laurus nobilis L.): isolation and identification of haptens. Arch Dermatol Res. 1984;276(3):178-81. doi: 10.1007/BF00414016. [PubMed:6476889  ]