NP-MRD: Showing NP-Card for 2-(6-ethenyl-4-hydroxy-6-methyl-3-methylidene-2-oxo-tetrahydro-3ah-1-benzofuran-7-yl)prop-2-enal (NP0321076)

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Record Information

Version

2.0

Created at

2022-09-11 23:05:28 UTC

Updated at

2022-09-11 23:05:29 UTC

NP-MRD ID

NP0321076

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2-(6-ethenyl-4-hydroxy-6-methyl-3-methylidene-2-oxo-tetrahydro-3ah-1-benzofuran-7-yl)prop-2-enal

Description

NSC645991 belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units. 2-(6-ethenyl-4-hydroxy-6-methyl-3-methylidene-2-oxo-tetrahydro-3ah-1-benzofuran-7-yl)prop-2-enal is found in Centaurea paui. NSC645991 is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 37 38  0  0  0  0  0  0  0  0999 V2000
   -1.2507   -1.8258   -1.8666 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2981   -1.7752   -0.5825 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9992   -0.7947    0.4226 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1857   -0.7970    1.4190 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1570   -1.3332    1.3161 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4789   -1.1787    0.5634 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4614   -1.7056    1.3659 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6958    0.2661    0.3703 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8566    0.7107   -0.3800 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0509    0.1858   -0.5218 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4218    1.9580   -1.0061 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0992    2.7999   -1.6716 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0369    2.1018   -0.7440 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5889    0.7635   -0.5910 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6849    0.6027    0.1366 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.7793    1.5188   -0.2372 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0050    2.5912    0.5455 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6573    1.4133   -1.3636 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5510    2.2732   -1.5629 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5392   -2.7125   -2.4075 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9312   -1.0019   -2.4690 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6646   -2.7497   -0.1214 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1369   -0.9488    0.8567 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1986    0.1149    2.0102 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1051   -1.6628    2.1090 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0652   -2.3532    1.6119 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1970   -0.6269    2.1673 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4004   -1.7476   -0.3820 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3611   -2.6771    1.4540 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5905    0.7961    1.3353 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2428   -0.7478    0.0003 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8367    0.6105   -1.1090 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7294    0.2855   -1.5438 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4004    1.0005    1.2032 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3716    2.7140    1.3977 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7735    3.3099    0.3564 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6078    0.6223   -2.0811 H   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  1  0
  3  5  1  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  8 14  1  0
 14 13  1  0
 13 11  1  0
 11 12  2  0
 11  9  1  0
  9 10  2  3
 14 15  1  0
 15 16  1  0
 16 17  2  3
 16 18  1  0
 18 19  2  0
  3  2  1  6
  2  1  2  3
 15  3  1  0
  9  8  1  0
  4 23  1  0
  4 24  1  0
  4 25  1  0
  5 26  1  0
  5 27  1  0
  6 28  1  6
  7 29  1  0
  8 30  1  1
 14 33  1  6
 10 31  1  0
 10 32  1  0
 15 34  1  1
 17 35  1  0
 17 36  1  0
 18 37  1  0
  2 22  1  0
  1 20  1  0
  1 21  1  0
M  END


  Mrv1533004181500372D          

 19 20  0  0  0  0            999 V2000
    3.6345    2.7107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -0.1271    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    2.1904    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1712    1.5229    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    0.8555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8838    0.0709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    3.1729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    3.5854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    3.5854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    4.4104    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1648    1.7922    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4469    1.0169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  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
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
  6 11  1  0  0  0  0
 11 12  2  0  0  0  0
  7 13  1  0  0  0  0
  2 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
 16 17  2  0  0  0  0
  2 18  1  0  0  0  0
 18 19  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0321076

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1(CC(O)C2C(OC(=O)C2=C)C1C(=C)C=O)C=C

> <INCHI_IDENTIFIER>
InChI=1S/C15H18O4/c1-5-15(4)6-10(17)11-9(3)14(18)19-13(11)12(15)8(2)7-16/h5,7,10-13,17H,1-3,6H2,4H3

> <INCHI_KEY>
ZTRSVJILTKDCGR-UHFFFAOYSA-N

> <FORMULA>
C15H18O4

> <MOLECULAR_WEIGHT>
262.305

> <EXACT_MASS>
262.12050906

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
37

> <JCHEM_AVERAGE_POLARIZABILITY>
27.241760056784273

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-(6-ethenyl-4-hydroxy-6-methyl-3-methylidene-2-oxo-octahydro-1-benzofuran-7-yl)prop-2-enal

> <ALOGPS_LOGP>
1.13

> <JCHEM_LOGP>
1.2835815149999996

> <ALOGPS_LOGS>
-2.34

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.752604781476162

> <JCHEM_PKA_STRONGEST_BASIC>
-2.907010668582325

> <JCHEM_POLAR_SURFACE_AREA>
63.6

> <JCHEM_REFRACTIVITY>
70.32919999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.20e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-(6-ethenyl-4-hydroxy-6-methyl-3-methylidene-2-oxo-tetrahydro-3aH-1-benzofuran-7-yl)prop-2-enal

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 18-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   18-APR-15         0                                  
HETATM    1  C   UNK     0       6.784   5.060   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.258   3.613   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.258   2.073   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.924   1.303   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       4.924  -0.237   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       3.590   2.073   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.590   3.613   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       2.126   4.089   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       1.220   2.843   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      -0.320   2.843   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       2.126   1.597   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.650   0.132   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.924   4.383   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.924   5.923   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.590   6.693   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.258   6.693   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       6.258   8.233   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       7.774   3.345   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       8.301   1.898   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   13   18                                             
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7   11                                                  
CONECT    7    6    8   13                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9    6   12                                                  
CONECT   12   11                                                            
CONECT   13    7    2   14                                                  
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17                                                       
CONECT   17   16                                                            
CONECT   18    2   19                                                       
CONECT   19   18                                                            
MASTER        0    0    0    0    0    0    0    0   19    0   40    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₅H₁₈O₄

Average Mass

262.3050 Da

Monoisotopic Mass

262.12051 Da

IUPAC Name

2-(6-ethenyl-4-hydroxy-6-methyl-3-methylidene-2-oxo-octahydro-1-benzofuran-7-yl)prop-2-enal

Traditional Name

2-(6-ethenyl-4-hydroxy-6-methyl-3-methylidene-2-oxo-tetrahydro-3aH-1-benzofuran-7-yl)prop-2-enal

CAS Registry Number

Not Available

SMILES

CC1(CC(O)C2C(OC(=O)C2=C)C1C(=C)C=O)C=C

InChI Identifier

InChI=1S/C15H18O4/c1-5-15(4)6-10(17)11-9(3)14(18)19-13(11)12(15)8(2)7-16/h5,7,10-13,17H,1-3,6H2,4H3

InChI Key

ZTRSVJILTKDCGR-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Centaurea paui	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Diterpenoids

Alternative Parents

Substituents

Diterpenoid
Elemanolide-skeleton
Benzofuran
Gamma butyrolactone
Alpha,beta-unsaturated aldehyde
Cyclic alcohol
Enal
Tetrahydrofuran
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Lactone
Carboxylic acid ester
Secondary alcohol
Monocarboxylic acid or derivatives
Oxacycle
Carboxylic acid derivative
Organoheterocyclic compound
Hydrocarbon derivative
Organic oxide
Aldehyde
Organooxygen compound
Alcohol
Organic oxygen compound
Carbonyl group
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	1.13	ALOGPS
logP	1.28	ChemAxon
logS	-2.3	ALOGPS
pKa (Strongest Acidic)	14.75	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	63.6 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	70.33 m³·mol⁻¹	ChemAxon
Polarizability	27.24 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

495207

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 2-(6-ethenyl-4-hydroxy-6-methyl-3-methylidene-2-oxo-tetrahydro-3ah-1-benzofuran-7-yl)prop-2-enal (NP0321076)

MOL for NP0321076 (2-(6-ethenyl-4-hydroxy-6-methyl-3-methylidene-2-oxo-tetrahydro-3ah-1-benzofuran-7-yl)prop-2-enal)

3D MOL for NP0321076 (2-(6-ethenyl-4-hydroxy-6-methyl-3-methylidene-2-oxo-tetrahydro-3ah-1-benzofuran-7-yl)prop-2-enal)

3D SDF for NP0321076 (2-(6-ethenyl-4-hydroxy-6-methyl-3-methylidene-2-oxo-tetrahydro-3ah-1-benzofuran-7-yl)prop-2-enal)

3D-SDF for NP0321076 (2-(6-ethenyl-4-hydroxy-6-methyl-3-methylidene-2-oxo-tetrahydro-3ah-1-benzofuran-7-yl)prop-2-enal)

PDB for NP0321076 (2-(6-ethenyl-4-hydroxy-6-methyl-3-methylidene-2-oxo-tetrahydro-3ah-1-benzofuran-7-yl)prop-2-enal)

3D PDB for NP0321076 (2-(6-ethenyl-4-hydroxy-6-methyl-3-methylidene-2-oxo-tetrahydro-3ah-1-benzofuran-7-yl)prop-2-enal)

SMILES for NP0321076 (2-(6-ethenyl-4-hydroxy-6-methyl-3-methylidene-2-oxo-tetrahydro-3ah-1-benzofuran-7-yl)prop-2-enal)

INCHI for NP0321076 (2-(6-ethenyl-4-hydroxy-6-methyl-3-methylidene-2-oxo-tetrahydro-3ah-1-benzofuran-7-yl)prop-2-enal)

Structure for NP0321076 (2-(6-ethenyl-4-hydroxy-6-methyl-3-methylidene-2-oxo-tetrahydro-3ah-1-benzofuran-7-yl)prop-2-enal)

3D Structure for NP0321076 (2-(6-ethenyl-4-hydroxy-6-methyl-3-methylidene-2-oxo-tetrahydro-3ah-1-benzofuran-7-yl)prop-2-enal)