NP-MRD: Showing NP-Card for (2e)-2-{2-[(4as,8as)-2,5,5,8a-tetramethyl-3,4,4a,6,7,8-hexahydronaphthalen-1-yl]ethyl}-4-[(2r)-3-(hydroxymethyl)-5-oxo-2h-furan-2-yl]but-2-enal (NP0199074)

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Record Information

Version

1.0

Created at

2022-09-04 17:38:57 UTC

Updated at

2022-09-04 17:38:57 UTC

NP-MRD ID

NP0199074

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2e)-2-{2-[(4as,8as)-2,5,5,8a-tetramethyl-3,4,4a,6,7,8-hexahydronaphthalen-1-yl]ethyl}-4-[(2r)-3-(hydroxymethyl)-5-oxo-2h-furan-2-yl]but-2-enal

Description

(2E)-2-{2-[(4aS,8aS)-2,5,5,8a-tetramethyl-3,4,4a,5,6,7,8,8a-octahydronaphthalen-1-yl]ethyl}-4-[(2R)-3-(hydroxymethyl)-5-oxo-2,5-dihydrofuran-2-yl]but-2-enal belongs to the class of organic compounds known as diterpene lactones. These are diterpenoids containing a lactone moiety. (2e)-2-{2-[(4as,8as)-2,5,5,8a-tetramethyl-3,4,4a,6,7,8-hexahydronaphthalen-1-yl]ethyl}-4-[(2r)-3-(hydroxymethyl)-5-oxo-2h-furan-2-yl]but-2-enal is found in Luffariella geometrica. It was first documented in 2012 (PMID: 36070501). Based on a literature review a significant number of articles have been published on (2E)-2-{2-[(4aS,8aS)-2,5,5,8a-tetramethyl-3,4,4a,5,6,7,8,8a-octahydronaphthalen-1-yl]ethyl}-4-[(2R)-3-(hydroxymethyl)-5-oxo-2,5-dihydrofuran-2-yl]but-2-enal (PMID: 36070500) (PMID: 36070964) (PMID: 36070963) (PMID: 36070962).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309042219382D          

 29 31  0  0  1  0            999 V2000
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    1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

     RDKit          3D

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M  END


  Mrv1652309042219382D          

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M  END
> <DATABASE_ID>
NP0199074

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1=C(CC\C(C=O)=C/C[C@H]2OC(=O)C=C2CO)[C@@]2(C)CCCC(C)(C)[C@@H]2CC1

> <INCHI_IDENTIFIER>
InChI=1S/C25H36O4/c1-17-6-11-22-24(2,3)12-5-13-25(22,4)20(17)9-7-18(15-26)8-10-21-19(16-27)14-23(28)29-21/h8,14-15,21-22,27H,5-7,9-13,16H2,1-4H3/b18-8+/t21-,22+,25-/m1/s1

> <INCHI_KEY>
LJXILPIFWYMKCJ-HSACWFNSSA-N

> <FORMULA>
C25H36O4

> <MOLECULAR_WEIGHT>
400.559

> <EXACT_MASS>
400.261359639

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
65

> <JCHEM_AVERAGE_POLARIZABILITY>
45.40328303504709

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2E)-2-{2-[(4aS,8aS)-2,5,5,8a-tetramethyl-3,4,4a,5,6,7,8,8a-octahydronaphthalen-1-yl]ethyl}-4-[(2R)-3-(hydroxymethyl)-5-oxo-2,5-dihydrofuran-2-yl]but-2-enal

> <JCHEM_LOGP>
4.457006345333334

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
15.608204738594608

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.192545681610676

> <JCHEM_PKA_STRONGEST_BASIC>
-2.79100750560841

> <JCHEM_POLAR_SURFACE_AREA>
63.60000000000001

> <JCHEM_REFRACTIVITY>
117.1195

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(2E)-2-{2-[(4aS,8aS)-2,5,5,8a-tetramethyl-3,4,4a,6,7,8-hexahydronaphthalen-1-yl]ethyl}-4-[(2R)-3-(hydroxymethyl)-5-oxo-2H-furan-2-yl]but-2-enal

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-22         0                                  
HETATM    1  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       2.667   6.160   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -2.667   4.620   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -4.074   3.994   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      -5.105   5.138   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      -6.636   4.977   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      -4.335   6.472   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -2.828   6.152   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -1.684   7.182   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -0.219   6.706   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.001   0.770   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       6.325  -4.260   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       4.345  -4.260   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   29                                                  
CONECT    3    2    4   19                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    9                                                  
CONECT    7    6    8                                                       
CONECT    8    7                                                            
CONECT    9    6   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   16                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15   11   17                                                  
CONECT   17   16   18                                                       
CONECT   18   17                                                            
CONECT   19    3   20   21   27                                             
CONECT   20   19                                                            
CONECT   21   19   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25   26   27                                             
CONECT   25   24                                                            
CONECT   26   24                                                            
CONECT   27   24   19   28                                                  
CONECT   28   27   29                                                       
CONECT   29   28    2                                                       
MASTER        0    0    0    0    0    0    0    0   29    0   62    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₅H₃₆O₄

Average Mass

400.5590 Da

Monoisotopic Mass

400.26136 Da

IUPAC Name

(2E)-2-{2-[(4aS,8aS)-2,5,5,8a-tetramethyl-3,4,4a,5,6,7,8,8a-octahydronaphthalen-1-yl]ethyl}-4-[(2R)-3-(hydroxymethyl)-5-oxo-2,5-dihydrofuran-2-yl]but-2-enal

Traditional Name

(2E)-2-{2-[(4aS,8aS)-2,5,5,8a-tetramethyl-3,4,4a,6,7,8-hexahydronaphthalen-1-yl]ethyl}-4-[(2R)-3-(hydroxymethyl)-5-oxo-2H-furan-2-yl]but-2-enal

CAS Registry Number

Not Available

SMILES

CC1=C(CC\C(C=O)=C/C[C@H]2OC(=O)C=C2CO)[C@@]2(C)CCCC(C)(C)[C@@H]2CC1

InChI Identifier

InChI=1S/C25H36O4/c1-17-6-11-22-24(2,3)12-5-13-25(22,4)20(17)9-7-18(15-26)8-10-21-19(16-27)14-23(28)29-21/h8,14-15,21-22,27H,5-7,9-13,16H2,1-4H3/b18-8+/t21-,22+,25-/m1/s1

InChI Key

LJXILPIFWYMKCJ-HSACWFNSSA-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
Luffariella geometrica	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
Labdane diterpenoid
Diterpenoid
2-furanone
Alpha,beta-unsaturated aldehyde
Dihydrofuran
Enal
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Lactone
Carboxylic acid ester
Monocarboxylic acid or derivatives
Oxacycle
Carboxylic acid derivative
Organoheterocyclic compound
Hydrocarbon derivative
Organic oxide
Aldehyde
Carbonyl group
Organooxygen compound
Primary alcohol
Alcohol
Organic oxygen 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	4.46	ChemAxon
pKa (Strongest Acidic)	6.19	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	63.6 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	117.12 m³·mol⁻¹	ChemAxon
Polarizability	45.4 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	Yes	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

8561729

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10386287

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Authors unspecified: Thalidomide. 2012. [PubMed:36070501 ]
Authors unspecified: Lenalidomide. 2012. [PubMed:36070500 ]
Uehara M, Wada-Hiraike O, Koga K, Yamamoto N, Hirano M, Harada M, Hirota Y, Osuga Y: Prediction of the final menstrual period in women taking Dienogest using estradiol and follicle-stimulating hormone values: a case-control study. Endocr J. 2022 Sep 7. doi: 10.1507/endocrj.EJ22-0158. [PubMed:36070964 ]
Oginosawa Y: Validation of the Implantable Cardioverter-Defibrillators Indication Criteria for Nonischemic Cardiomyopathy- Why? When? How? Circ J. 2022 Sep 6. doi: 10.1253/circj.CJ-22-0478. [PubMed:36070963 ]
Kodera S, Morita H, Nishi H, Takeda N, Ando J, Komuro I: Cost-Effectiveness of Dapagliflozin for Chronic Kidney Disease in Japan. Circ J. 2022 Sep 6. doi: 10.1253/circj.CJ-22-0086. [PubMed:36070962 ]
LOTUS database [Link]

Showing NP-Card for (2e)-2-{2-[(4as,8as)-2,5,5,8a-tetramethyl-3,4,4a,6,7,8-hexahydronaphthalen-1-yl]ethyl}-4-[(2r)-3-(hydroxymethyl)-5-oxo-2h-furan-2-yl]but-2-enal (NP0199074)

MOL for NP0199074 ((2e)-2-{2-[(4as,8as)-2,5,5,8a-tetramethyl-3,4,4a,6,7,8-hexahydronaphthalen-1-yl]ethyl}-4-[(2r)-3-(hydroxymethyl)-5-oxo-2h-furan-2-yl]but-2-enal)

3D MOL for NP0199074 ((2e)-2-{2-[(4as,8as)-2,5,5,8a-tetramethyl-3,4,4a,6,7,8-hexahydronaphthalen-1-yl]ethyl}-4-[(2r)-3-(hydroxymethyl)-5-oxo-2h-furan-2-yl]but-2-enal)

3D SDF for NP0199074 ((2e)-2-{2-[(4as,8as)-2,5,5,8a-tetramethyl-3,4,4a,6,7,8-hexahydronaphthalen-1-yl]ethyl}-4-[(2r)-3-(hydroxymethyl)-5-oxo-2h-furan-2-yl]but-2-enal)

3D-SDF for NP0199074 ((2e)-2-{2-[(4as,8as)-2,5,5,8a-tetramethyl-3,4,4a,6,7,8-hexahydronaphthalen-1-yl]ethyl}-4-[(2r)-3-(hydroxymethyl)-5-oxo-2h-furan-2-yl]but-2-enal)

PDB for NP0199074 ((2e)-2-{2-[(4as,8as)-2,5,5,8a-tetramethyl-3,4,4a,6,7,8-hexahydronaphthalen-1-yl]ethyl}-4-[(2r)-3-(hydroxymethyl)-5-oxo-2h-furan-2-yl]but-2-enal)

3D PDB for NP0199074 ((2e)-2-{2-[(4as,8as)-2,5,5,8a-tetramethyl-3,4,4a,6,7,8-hexahydronaphthalen-1-yl]ethyl}-4-[(2r)-3-(hydroxymethyl)-5-oxo-2h-furan-2-yl]but-2-enal)

SMILES for NP0199074 ((2e)-2-{2-[(4as,8as)-2,5,5,8a-tetramethyl-3,4,4a,6,7,8-hexahydronaphthalen-1-yl]ethyl}-4-[(2r)-3-(hydroxymethyl)-5-oxo-2h-furan-2-yl]but-2-enal)

INCHI for NP0199074 ((2e)-2-{2-[(4as,8as)-2,5,5,8a-tetramethyl-3,4,4a,6,7,8-hexahydronaphthalen-1-yl]ethyl}-4-[(2r)-3-(hydroxymethyl)-5-oxo-2h-furan-2-yl]but-2-enal)

Structure for NP0199074 ((2e)-2-{2-[(4as,8as)-2,5,5,8a-tetramethyl-3,4,4a,6,7,8-hexahydronaphthalen-1-yl]ethyl}-4-[(2r)-3-(hydroxymethyl)-5-oxo-2h-furan-2-yl]but-2-enal)

3D Structure for NP0199074 ((2e)-2-{2-[(4as,8as)-2,5,5,8a-tetramethyl-3,4,4a,6,7,8-hexahydronaphthalen-1-yl]ethyl}-4-[(2r)-3-(hydroxymethyl)-5-oxo-2h-furan-2-yl]but-2-enal)