NP-MRD: Showing NP-Card for (1r,2r,4as,8as)-1-{2-[(5s)-5-hydroxy-2-oxo-5h-furan-3-yl]ethyl}-1,2-dimethyl-5-({[(2z)-2-methylbut-2-enoyl]oxy}methyl)-2,3,4,7,8,8a-hexahydronaphthalene-4a-carboxylic acid (NP0236348)

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Record Information

Version

2.0

Created at

2022-09-06 19:13:31 UTC

Updated at

2022-09-06 19:13:31 UTC

NP-MRD ID

NP0236348

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r,2r,4as,8as)-1-{2-[(5s)-5-hydroxy-2-oxo-5h-furan-3-yl]ethyl}-1,2-dimethyl-5-({[(2z)-2-methylbut-2-enoyl]oxy}methyl)-2,3,4,7,8,8a-hexahydronaphthalene-4a-carboxylic acid

Description

(1R,2R,4aS,8aS)-1-{2-[(5S)-5-hydroxy-2-oxo-2,5-dihydrofuran-3-yl]ethyl}-1,2-dimethyl-5-({[(2Z)-2-methylbut-2-enoyl]oxy}methyl)-1,2,3,4,4a,7,8,8a-octahydronaphthalene-4a-carboxylic acid belongs to the class of organic compounds known as diterpene lactones. These are diterpenoids containing a lactone moiety. (1r,2r,4as,8as)-1-{2-[(5s)-5-hydroxy-2-oxo-5h-furan-3-yl]ethyl}-1,2-dimethyl-5-({[(2z)-2-methylbut-2-enoyl]oxy}methyl)-2,3,4,7,8,8a-hexahydronaphthalene-4a-carboxylic acid is found in Solidago virgaurea. Based on a literature review very few articles have been published on (1R,2R,4aS,8aS)-1-{2-[(5S)-5-hydroxy-2-oxo-2,5-dihydrofuran-3-yl]ethyl}-1,2-dimethyl-5-({[(2Z)-2-methylbut-2-enoyl]oxy}methyl)-1,2,3,4,4a,7,8,8a-octahydronaphthalene-4a-carboxylic acid.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309062221132D          

 32 34  0  0  1  0            999 V2000
   -0.7145    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

     RDKit          3D

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    2.8898   -0.3305    0.1574 C   0  0  0  0  0  0  0  0  0  0  0  0
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    4.0883    1.5933    1.1305 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1652309062221132D          

 32 34  0  0  1  0            999 V2000
   -0.7145    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END
> <DATABASE_ID>
NP0236348

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C\C=C(\C)C(=O)OCC1=CCC[C@H]2[C@](C)(CCC3=C[C@@H](O)OC3=O)[C@H](C)CC[C@@]12C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C25H34O7/c1-5-15(2)21(27)31-14-18-7-6-8-19-24(4,11-10-17-13-20(26)32-22(17)28)16(3)9-12-25(18,19)23(29)30/h5,7,13,16,19-20,26H,6,8-12,14H2,1-4H3,(H,29,30)/b15-5-/t16-,19+,20+,24-,25-/m1/s1

> <INCHI_KEY>
AWOYIEKZALIOEL-WRKMGEQLSA-N

> <FORMULA>
C25H34O7

> <MOLECULAR_WEIGHT>
446.54

> <EXACT_MASS>
446.230453435

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
66

> <JCHEM_AVERAGE_POLARIZABILITY>
47.325003458939676

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,2R,4aS,8aS)-1-{2-[(5S)-5-hydroxy-2-oxo-2,5-dihydrofuran-3-yl]ethyl}-1,2-dimethyl-5-({[(2Z)-2-methylbut-2-enoyl]oxy}methyl)-1,2,3,4,4a,7,8,8a-octahydronaphthalene-4a-carboxylic acid

> <JCHEM_LOGP>
4.950508568333332

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
11.829957809528011

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.265658610277641

> <JCHEM_PKA_STRONGEST_BASIC>
-4.1622494659179745

> <JCHEM_POLAR_SURFACE_AREA>
110.13000000000002

> <JCHEM_REFRACTIVITY>
119.70289999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2R,4aS,8aS)-1-{2-[(5S)-5-hydroxy-2-oxo-5H-furan-3-yl]ethyl}-1,2-dimethyl-5-({[(2Z)-2-methylbut-2-enoyl]oxy}methyl)-2,3,4,7,8,8a-hexahydronaphthalene-4a-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-SEP-22         0                                  
HETATM    1  C   UNK     0      -1.334   6.930   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.667   6.160   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.667   4.620   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -4.001   3.850   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       0.000   4.620   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0      -1.334   2.310   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.334   0.770   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       0.707   2.177   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       2.667   1.540   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+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  -2.310   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       3.390  -4.440   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       1.944  -4.440   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       2.760  -5.746   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       2.037  -7.105   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       2.713  -8.490   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       1.605  -9.559   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       1.819 -11.084   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0       0.245  -8.836   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       0.512  -7.320   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      -0.557  -6.212   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   14                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   22                                                  
CONECT   14   13    9   15   18                                             
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15                                                            
CONECT   18   14   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   13   23   24                                             
CONECT   23   22                                                            
CONECT   24   22   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27   31                                                  
CONECT   27   26   28                                                       
CONECT   28   27   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   31                                                       
CONECT   31   30   26   32                                                  
CONECT   32   31                                                            
MASTER        0    0    0    0    0    0    0    0   32    0   68    0
END

View in JSmol

Synonyms

Value	Source
(1R,2R,4AS,8as)-1-{2-[(5S)-5-hydroxy-2-oxo-2,5-dihydrofuran-3-yl]ethyl}-1,2-dimethyl-5-({[(2Z)-2-methylbut-2-enoyl]oxy}methyl)-1,2,3,4,4a,7,8,8a-octahydronaphthalene-4a-carboxylate	Generator

Chemical Formula

C₂₅H₃₄O₇

Average Mass

446.5400 Da

Monoisotopic Mass

446.23045 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

C\C=C(\C)C(=O)OCC1=CCC[C@H]2[C@](C)(CCC3=C[C@@H](O)OC3=O)[C@H](C)CC[C@@]12C(O)=O

InChI Identifier

InChI=1S/C25H34O7/c1-5-15(2)21(27)31-14-18-7-6-8-19-24(4,11-10-17-13-20(26)32-22(17)28)16(3)9-12-25(18,19)23(29)30/h5,7,13,16,19-20,26H,6,8-12,14H2,1-4H3,(H,29,30)/b15-5-/t16-,19+,20+,24-,25-/m1/s1

InChI Key

AWOYIEKZALIOEL-WRKMGEQLSA-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
Solidago virgaurea	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
Clerodane diterpenoid
Tricarboxylic acid or derivatives
Fatty acid ester
2-furanone
Fatty acyl
Dihydrofuran
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Carboxylic acid ester
Hemiacetal
Lactone
Organoheterocyclic compound
Oxacycle
Carboxylic acid
Carboxylic acid derivative
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Carbonyl group
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

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

163190030

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1r,2r,4as,8as)-1-{2-[(5s)-5-hydroxy-2-oxo-5h-furan-3-yl]ethyl}-1,2-dimethyl-5-({[(2z)-2-methylbut-2-enoyl]oxy}methyl)-2,3,4,7,8,8a-hexahydronaphthalene-4a-carboxylic acid (NP0236348)

MOL for NP0236348 ((1r,2r,4as,8as)-1-{2-[(5s)-5-hydroxy-2-oxo-5h-furan-3-yl]ethyl}-1,2-dimethyl-5-({[(2z)-2-methylbut-2-enoyl]oxy}methyl)-2,3,4,7,8,8a-hexahydronaphthalene-4a-carboxylic acid)

3D MOL for NP0236348 ((1r,2r,4as,8as)-1-{2-[(5s)-5-hydroxy-2-oxo-5h-furan-3-yl]ethyl}-1,2-dimethyl-5-({[(2z)-2-methylbut-2-enoyl]oxy}methyl)-2,3,4,7,8,8a-hexahydronaphthalene-4a-carboxylic acid)

3D SDF for NP0236348 ((1r,2r,4as,8as)-1-{2-[(5s)-5-hydroxy-2-oxo-5h-furan-3-yl]ethyl}-1,2-dimethyl-5-({[(2z)-2-methylbut-2-enoyl]oxy}methyl)-2,3,4,7,8,8a-hexahydronaphthalene-4a-carboxylic acid)

3D-SDF for NP0236348 ((1r,2r,4as,8as)-1-{2-[(5s)-5-hydroxy-2-oxo-5h-furan-3-yl]ethyl}-1,2-dimethyl-5-({[(2z)-2-methylbut-2-enoyl]oxy}methyl)-2,3,4,7,8,8a-hexahydronaphthalene-4a-carboxylic acid)

PDB for NP0236348 ((1r,2r,4as,8as)-1-{2-[(5s)-5-hydroxy-2-oxo-5h-furan-3-yl]ethyl}-1,2-dimethyl-5-({[(2z)-2-methylbut-2-enoyl]oxy}methyl)-2,3,4,7,8,8a-hexahydronaphthalene-4a-carboxylic acid)

3D PDB for NP0236348 ((1r,2r,4as,8as)-1-{2-[(5s)-5-hydroxy-2-oxo-5h-furan-3-yl]ethyl}-1,2-dimethyl-5-({[(2z)-2-methylbut-2-enoyl]oxy}methyl)-2,3,4,7,8,8a-hexahydronaphthalene-4a-carboxylic acid)

SMILES for NP0236348 ((1r,2r,4as,8as)-1-{2-[(5s)-5-hydroxy-2-oxo-5h-furan-3-yl]ethyl}-1,2-dimethyl-5-({[(2z)-2-methylbut-2-enoyl]oxy}methyl)-2,3,4,7,8,8a-hexahydronaphthalene-4a-carboxylic acid)

INCHI for NP0236348 ((1r,2r,4as,8as)-1-{2-[(5s)-5-hydroxy-2-oxo-5h-furan-3-yl]ethyl}-1,2-dimethyl-5-({[(2z)-2-methylbut-2-enoyl]oxy}methyl)-2,3,4,7,8,8a-hexahydronaphthalene-4a-carboxylic acid)

Structure for NP0236348 ((1r,2r,4as,8as)-1-{2-[(5s)-5-hydroxy-2-oxo-5h-furan-3-yl]ethyl}-1,2-dimethyl-5-({[(2z)-2-methylbut-2-enoyl]oxy}methyl)-2,3,4,7,8,8a-hexahydronaphthalene-4a-carboxylic acid)

3D Structure for NP0236348 ((1r,2r,4as,8as)-1-{2-[(5s)-5-hydroxy-2-oxo-5h-furan-3-yl]ethyl}-1,2-dimethyl-5-({[(2z)-2-methylbut-2-enoyl]oxy}methyl)-2,3,4,7,8,8a-hexahydronaphthalene-4a-carboxylic acid)