NP-MRD: Showing NP-Card for 2-[(3ar,5ar,6r,9ar)-6-isopropyl-3a,5a-dimethyl-2,8-dioxo-3h,4h,5h,6h,7h-azuleno[5,6-b]furan-9a-yl]prop-2-enal (NP0218225)

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Record Information

Version

2.0

Created at

2022-09-05 18:49:39 UTC

Updated at

2022-09-05 18:49:40 UTC

NP-MRD ID

NP0218225

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2-[(3ar,5ar,6r,9ar)-6-isopropyl-3a,5a-dimethyl-2,8-dioxo-3h,4h,5h,6h,7h-azuleno[5,6-b]furan-9a-yl]prop-2-enal

Description

Lepistal belongs to the class of organic compounds known as diterpene lactones. These are diterpenoids containing a lactone moiety. 2-[(3ar,5ar,6r,9ar)-6-isopropyl-3a,5a-dimethyl-2,8-dioxo-3h,4h,5h,6h,7h-azuleno[5,6-b]furan-9a-yl]prop-2-enal is found in Lepista sordida. Based on a literature review very few articles have been published on Lepistal.

Structure

MOL SDF PDB SMILES InChI

  Mrv1652309052220492D          

 24 26  0  0  1  0            999 V2000
    1.1606    0.5680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8558    0.1239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5881    0.5039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6251    1.3281    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8188   -0.7003    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5621   -0.3423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3054   -0.7003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0136   -0.2772    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0876    0.5445    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6349   -0.8199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3107   -1.5786    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.7338   -2.2868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5587   -2.2744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3321   -3.0073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4890   -1.5046    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.8132   -2.2632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9746   -2.1496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1496   -2.1496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6352   -1.5046    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3110   -2.2632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8136   -1.5786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4893   -0.8199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3150   -0.6364    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1106   -0.2772    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  2  0  0  0  0
  5  2  1  1  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  6  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
 11 15  1  0  0  0  0
  7 15  1  0  0  0  0
 15 16  1  6  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
  5 19  1  0  0  0  0
 19 20  1  1  0  0  0
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
  5 24  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0218225

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)[C@H]1CC(=O)C2=C[C@]3(OC(=O)C[C@@]3(C)CC[C@]12C)C(=C)C=O

> <INCHI_IDENTIFIER>
InChI=1S/C20H26O4/c1-12(2)14-8-16(22)15-9-20(13(3)11-21)18(4,10-17(23)24-20)6-7-19(14,15)5/h9,11-12,14H,3,6-8,10H2,1-2,4-5H3/t14-,18-,19-,20+/m1/s1

> <INCHI_KEY>
XDEMETQGFBYWPP-DMSXTEQDSA-N

> <FORMULA>
C20H26O4

> <MOLECULAR_WEIGHT>
330.424

> <EXACT_MASS>
330.183109317

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
50

> <JCHEM_AVERAGE_POLARIZABILITY>
35.827355320772945

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-[(3aR,5aR,6R,9aR)-3a,5a-dimethyl-2,8-dioxo-6-(propan-2-yl)-2H,3H,3aH,4H,5H,5aH,6H,7H,8H,9aH-azuleno[5,6-b]furan-9a-yl]prop-2-enal

> <JCHEM_LOGP>
3.1450695343333335

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-5.829810635300723

> <JCHEM_POLAR_SURFACE_AREA>
60.44

> <JCHEM_REFRACTIVITY>
91.10499999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
2-[(3aR,5aR,6R,9aR)-6-isopropyl-3a,5a-dimethyl-2,8-dioxo-3H,4H,5H,6H,7H-azuleno[5,6-b]furan-9a-yl]prop-2-enal

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 05-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-SEP-22         0                                  
HETATM    1  C   UNK     0       2.166   1.060   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.464   0.231   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.831   0.941   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       4.900   2.479   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       3.395  -1.307   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.783  -0.639   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.170  -1.307   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.492  -0.517   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       7.630   1.016   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       8.652  -1.531   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.047  -2.947   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.836  -4.269   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      10.376  -4.246   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.086  -5.614   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.513  -2.809   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       7.118  -4.225   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.553  -4.013   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.013  -4.013   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.052  -2.809   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.447  -4.225   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       1.519  -2.947   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       0.913  -1.531   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      -0.588  -1.188   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       2.073  -0.517   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    5                                                  
CONECT    3    2    4                                                       
CONECT    4    3                                                            
CONECT    5    2    6   19   24                                             
CONECT    6    5    7                                                       
CONECT    7    6    8   15                                                  
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10   12   15                                                  
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12                                                            
CONECT   15   11    7   16   17                                             
CONECT   16   15                                                            
CONECT   17   15   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18    5   20   21                                             
CONECT   20   19                                                            
CONECT   21   19   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22    5                                                       
MASTER        0    0    0    0    0    0    0    0   24    0   52    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₀H₂₆O₄

Average Mass

330.4240 Da

Monoisotopic Mass

330.18311 Da

IUPAC Name

2-[(3aR,5aR,6R,9aR)-3a,5a-dimethyl-2,8-dioxo-6-(propan-2-yl)-2H,3H,3aH,4H,5H,5aH,6H,7H,8H,9aH-azuleno[5,6-b]furan-9a-yl]prop-2-enal

Traditional Name

2-[(3aR,5aR,6R,9aR)-6-isopropyl-3a,5a-dimethyl-2,8-dioxo-3H,4H,5H,6H,7H-azuleno[5,6-b]furan-9a-yl]prop-2-enal

CAS Registry Number

Not Available

SMILES

CC(C)[C@H]1CC(=O)C2=C[C@]3(OC(=O)C[C@@]3(C)CC[C@]12C)C(=C)C=O

InChI Identifier

InChI=1S/C20H26O4/c1-12(2)14-8-16(22)15-9-20(13(3)11-21)18(4,10-17(23)24-20)6-7-19(14,15)5/h9,11-12,14H,3,6-8,10H2,1-2,4-5H3/t14-,18-,19-,20+/m1/s1

InChI Key

XDEMETQGFBYWPP-DMSXTEQDSA-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
Lepista sordida	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as diterpene lactones. These are diterpenoids containing a lactone moiety.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Diterpene lactones

Alternative Parents

Substituents

Diterpene lactone
Diterpenoid
Gamma butyrolactone
Alpha,beta-unsaturated aldehyde
Enal
Oxolane
Carboxylic acid ester
Ketone
Lactone
Organoheterocyclic compound
Oxacycle
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Hydrocarbon derivative
Organic oxide
Aldehyde
Carbonyl group
Organic oxygen compound
Organooxygen compound
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	3.15	ChemAxon
pKa (Strongest Basic)	-5.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	60.44 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	91.1 m³·mol⁻¹	ChemAxon
Polarizability	35.83 Å³	ChemAxon
Number of Rings	3	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

8195116

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10019543

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 2-[(3ar,5ar,6r,9ar)-6-isopropyl-3a,5a-dimethyl-2,8-dioxo-3h,4h,5h,6h,7h-azuleno[5,6-b]furan-9a-yl]prop-2-enal (NP0218225)

MOL for NP0218225 (2-[(3ar,5ar,6r,9ar)-6-isopropyl-3a,5a-dimethyl-2,8-dioxo-3h,4h,5h,6h,7h-azuleno[5,6-b]furan-9a-yl]prop-2-enal)

3D MOL for NP0218225 (2-[(3ar,5ar,6r,9ar)-6-isopropyl-3a,5a-dimethyl-2,8-dioxo-3h,4h,5h,6h,7h-azuleno[5,6-b]furan-9a-yl]prop-2-enal)

3D SDF for NP0218225 (2-[(3ar,5ar,6r,9ar)-6-isopropyl-3a,5a-dimethyl-2,8-dioxo-3h,4h,5h,6h,7h-azuleno[5,6-b]furan-9a-yl]prop-2-enal)

3D-SDF for NP0218225 (2-[(3ar,5ar,6r,9ar)-6-isopropyl-3a,5a-dimethyl-2,8-dioxo-3h,4h,5h,6h,7h-azuleno[5,6-b]furan-9a-yl]prop-2-enal)

PDB for NP0218225 (2-[(3ar,5ar,6r,9ar)-6-isopropyl-3a,5a-dimethyl-2,8-dioxo-3h,4h,5h,6h,7h-azuleno[5,6-b]furan-9a-yl]prop-2-enal)

3D PDB for NP0218225 (2-[(3ar,5ar,6r,9ar)-6-isopropyl-3a,5a-dimethyl-2,8-dioxo-3h,4h,5h,6h,7h-azuleno[5,6-b]furan-9a-yl]prop-2-enal)

SMILES for NP0218225 (2-[(3ar,5ar,6r,9ar)-6-isopropyl-3a,5a-dimethyl-2,8-dioxo-3h,4h,5h,6h,7h-azuleno[5,6-b]furan-9a-yl]prop-2-enal)

INCHI for NP0218225 (2-[(3ar,5ar,6r,9ar)-6-isopropyl-3a,5a-dimethyl-2,8-dioxo-3h,4h,5h,6h,7h-azuleno[5,6-b]furan-9a-yl]prop-2-enal)

Structure for NP0218225 (2-[(3ar,5ar,6r,9ar)-6-isopropyl-3a,5a-dimethyl-2,8-dioxo-3h,4h,5h,6h,7h-azuleno[5,6-b]furan-9a-yl]prop-2-enal)

3D Structure for NP0218225 (2-[(3ar,5ar,6r,9ar)-6-isopropyl-3a,5a-dimethyl-2,8-dioxo-3h,4h,5h,6h,7h-azuleno[5,6-b]furan-9a-yl]prop-2-enal)