NP-MRD: Showing NP-Card for (2s,4s,6e)-7-[(1s,3ar,4r,5s,7s,7as)-1-benzyl-3,3a,5-trihydroxy-7-methyl-6-methylidene-4,5,7,7a-tetrahydro-1h-isoindol-4-yl]-2-hydroxy-4-methylhept-6-en-3-one (NP0218689)

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Record Information

Version

2.0

Created at

2022-09-05 19:26:06 UTC

Updated at

2022-09-05 19:26:07 UTC

NP-MRD ID

NP0218689

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2s,4s,6e)-7-[(1s,3ar,4r,5s,7s,7as)-1-benzyl-3,3a,5-trihydroxy-7-methyl-6-methylidene-4,5,7,7a-tetrahydro-1h-isoindol-4-yl]-2-hydroxy-4-methylhept-6-en-3-one

Description

(2S,4S,6E)-7-[(1S,3aR,4R,5S,7S,7aS)-1-benzyl-3,3a,5-trihydroxy-7-methyl-6-methylidene-3a,4,5,6,7,7a-hexahydro-1H-isoindol-4-yl]-2-hydroxy-4-methylhept-6-en-3-one belongs to the class of organic compounds known as isoindoles. These are heteropolycyclic compounds with a structure containing isoindole, a benzo-fused pyrrole. (2s,4s,6e)-7-[(1s,3ar,4r,5s,7s,7as)-1-benzyl-3,3a,5-trihydroxy-7-methyl-6-methylidene-4,5,7,7a-tetrahydro-1h-isoindol-4-yl]-2-hydroxy-4-methylhept-6-en-3-one is found in Mariannaea elegans. Based on a literature review very few articles have been published on (2S,4S,6E)-7-[(1S,3aR,4R,5S,7S,7aS)-1-benzyl-3,3a,5-trihydroxy-7-methyl-6-methylidene-3a,4,5,6,7,7a-hexahydro-1H-isoindol-4-yl]-2-hydroxy-4-methylhept-6-en-3-one.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309052221262D          

 31 33  0  0  1  0            999 V2000
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    0.8250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6131    1.3770    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4201    1.2055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9721    1.8186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7791    1.6471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3311    2.2602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0762    3.0448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2692    3.2163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7172    2.6032    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2775    2.1307    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5429    2.0445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.3819    1.7224    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    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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M  END


  Mrv1652309052221262D          

 31 33  0  0  1  0            999 V2000
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    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END
> <DATABASE_ID>
NP0218689

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@H](O)C(=O)[C@@H](C)C\C=C\[C@@H]1[C@H](O)C(=C)[C@@H](C)[C@H]2[C@H](CC3=CC=CC=C3)N=C(O)[C@]12O

> <INCHI_IDENTIFIER>
InChI=1S/C25H33NO5/c1-14(22(28)17(4)27)9-8-12-19-23(29)16(3)15(2)21-20(26-24(30)25(19,21)31)13-18-10-6-5-7-11-18/h5-8,10-12,14-15,17,19-21,23,27,29,31H,3,9,13H2,1-2,4H3,(H,26,30)/b12-8+/t14-,15+,17-,19+,20-,21-,23+,25-/m0/s1

> <INCHI_KEY>
XKLGDBFKKUIZTH-ANJXINEASA-N

> <FORMULA>
C25H33NO5

> <MOLECULAR_WEIGHT>
427.541

> <EXACT_MASS>
427.235873167

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
64

> <JCHEM_AVERAGE_POLARIZABILITY>
46.78748077534868

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2S,4S,6E)-7-[(1S,3aR,4R,5S,7S,7aS)-1-benzyl-3,3a,5-trihydroxy-7-methyl-6-methylidene-3a,4,5,6,7,7a-hexahydro-1H-isoindol-4-yl]-2-hydroxy-4-methylhept-6-en-3-one

> <JCHEM_LOGP>
1.7129540624903925

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.20084938317747

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.0138140885581817

> <JCHEM_PKA_STRONGEST_BASIC>
4.720291818585655

> <JCHEM_POLAR_SURFACE_AREA>
110.35000000000002

> <JCHEM_REFRACTIVITY>
119.98920000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(2S,4S,6E)-7-[(1S,3aR,4R,5S,7S,7aS)-1-benzyl-3,3a,5-trihydroxy-7-methyl-6-methylidene-4,5,7,7a-tetrahydro-1H-isoindol-4-yl]-2-hydroxy-4-methylhept-6-en-3-one

> <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       1.334  -2.310   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      -0.000   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.000   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.144   2.570   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.651   2.250   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -3.681   3.395   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -5.188   3.075   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -6.218   4.219   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -5.742   5.684   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -4.236   6.004   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -3.205   4.859   0.000  0.00  0.00           C+0
HETATM   14  N   UNK     0      -0.518   3.977   0.000  0.00  0.00           N+0
HETATM   15  C   UNK     0       1.013   3.816   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       2.044   4.961   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       2.580   3.215   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       2.667   1.540   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   1.540   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       8.002   0.000   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       9.336   2.310   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       9.336   3.850   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      10.669   1.540   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      12.003   2.310   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      10.669   0.000   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       4.001  -0.770   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   30                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   17                                                  
CONECT    6    5    7   14                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   13                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12    8                                                       
CONECT   14    6   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15    5   18   19                                             
CONECT   18   17                                                            
CONECT   19   17   20   30                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27                                                            
CONECT   30   19    2   31                                                  
CONECT   31   30                                                            
MASTER        0    0    0    0    0    0    0    0   31    0   66    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₅H₃₃NO₅

Average Mass

427.5410 Da

Monoisotopic Mass

427.23587 Da

IUPAC Name

(2S,4S,6E)-7-[(1S,3aR,4R,5S,7S,7aS)-1-benzyl-3,3a,5-trihydroxy-7-methyl-6-methylidene-3a,4,5,6,7,7a-hexahydro-1H-isoindol-4-yl]-2-hydroxy-4-methylhept-6-en-3-one

Traditional Name

(2S,4S,6E)-7-[(1S,3aR,4R,5S,7S,7aS)-1-benzyl-3,3a,5-trihydroxy-7-methyl-6-methylidene-4,5,7,7a-tetrahydro-1H-isoindol-4-yl]-2-hydroxy-4-methylhept-6-en-3-one

CAS Registry Number

Not Available

SMILES

C[C@H](O)C(=O)[C@@H](C)C\C=C\[C@@H]1[C@H](O)C(=C)[C@@H](C)[C@H]2[C@H](CC3=CC=CC=C3)N=C(O)[C@]12O

InChI Identifier

InChI=1S/C25H33NO5/c1-14(22(28)17(4)27)9-8-12-19-23(29)16(3)15(2)21-20(26-24(30)25(19,21)31)13-18-10-6-5-7-11-18/h5-8,10-12,14-15,17,19-21,23,27,29,31H,3,9,13H2,1-2,4H3,(H,26,30)/b12-8+/t14-,15+,17-,19+,20-,21-,23+,25-/m0/s1

InChI Key

XKLGDBFKKUIZTH-ANJXINEASA-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
Mariannaea elegans	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as isoindoles. These are heteropolycyclic compounds with a structure containing isoindole, a benzo-fused pyrrole.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Isoindoles and derivatives

Sub Class

Isoindoles

Direct Parent

Isoindoles

Alternative Parents

Substituents

Isoindole
Benzenoid
Monosaccharide
Monocyclic benzene moiety
Acyloin
Cyclic carboximidic acid
Tertiary alcohol
Pyrroline
Cyclic alcohol
Alpha-hydroxy ketone
Secondary alcohol
Ketone
Azacycle
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Polyol
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Carbonyl group
Alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic 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	1.71	ChemAxon
pKa (Strongest Acidic)	2.01	ChemAxon
pKa (Strongest Basic)	4.72	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	110.35 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	119.99 m³·mol⁻¹	ChemAxon
Polarizability	46.79 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

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

163027871

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2s,4s,6e)-7-[(1s,3ar,4r,5s,7s,7as)-1-benzyl-3,3a,5-trihydroxy-7-methyl-6-methylidene-4,5,7,7a-tetrahydro-1h-isoindol-4-yl]-2-hydroxy-4-methylhept-6-en-3-one (NP0218689)

MOL for NP0218689 ((2s,4s,6e)-7-[(1s,3ar,4r,5s,7s,7as)-1-benzyl-3,3a,5-trihydroxy-7-methyl-6-methylidene-4,5,7,7a-tetrahydro-1h-isoindol-4-yl]-2-hydroxy-4-methylhept-6-en-3-one)

3D MOL for NP0218689 ((2s,4s,6e)-7-[(1s,3ar,4r,5s,7s,7as)-1-benzyl-3,3a,5-trihydroxy-7-methyl-6-methylidene-4,5,7,7a-tetrahydro-1h-isoindol-4-yl]-2-hydroxy-4-methylhept-6-en-3-one)

3D SDF for NP0218689 ((2s,4s,6e)-7-[(1s,3ar,4r,5s,7s,7as)-1-benzyl-3,3a,5-trihydroxy-7-methyl-6-methylidene-4,5,7,7a-tetrahydro-1h-isoindol-4-yl]-2-hydroxy-4-methylhept-6-en-3-one)

3D-SDF for NP0218689 ((2s,4s,6e)-7-[(1s,3ar,4r,5s,7s,7as)-1-benzyl-3,3a,5-trihydroxy-7-methyl-6-methylidene-4,5,7,7a-tetrahydro-1h-isoindol-4-yl]-2-hydroxy-4-methylhept-6-en-3-one)

PDB for NP0218689 ((2s,4s,6e)-7-[(1s,3ar,4r,5s,7s,7as)-1-benzyl-3,3a,5-trihydroxy-7-methyl-6-methylidene-4,5,7,7a-tetrahydro-1h-isoindol-4-yl]-2-hydroxy-4-methylhept-6-en-3-one)

3D PDB for NP0218689 ((2s,4s,6e)-7-[(1s,3ar,4r,5s,7s,7as)-1-benzyl-3,3a,5-trihydroxy-7-methyl-6-methylidene-4,5,7,7a-tetrahydro-1h-isoindol-4-yl]-2-hydroxy-4-methylhept-6-en-3-one)

SMILES for NP0218689 ((2s,4s,6e)-7-[(1s,3ar,4r,5s,7s,7as)-1-benzyl-3,3a,5-trihydroxy-7-methyl-6-methylidene-4,5,7,7a-tetrahydro-1h-isoindol-4-yl]-2-hydroxy-4-methylhept-6-en-3-one)

INCHI for NP0218689 ((2s,4s,6e)-7-[(1s,3ar,4r,5s,7s,7as)-1-benzyl-3,3a,5-trihydroxy-7-methyl-6-methylidene-4,5,7,7a-tetrahydro-1h-isoindol-4-yl]-2-hydroxy-4-methylhept-6-en-3-one)

Structure for NP0218689 ((2s,4s,6e)-7-[(1s,3ar,4r,5s,7s,7as)-1-benzyl-3,3a,5-trihydroxy-7-methyl-6-methylidene-4,5,7,7a-tetrahydro-1h-isoindol-4-yl]-2-hydroxy-4-methylhept-6-en-3-one)

3D Structure for NP0218689 ((2s,4s,6e)-7-[(1s,3ar,4r,5s,7s,7as)-1-benzyl-3,3a,5-trihydroxy-7-methyl-6-methylidene-4,5,7,7a-tetrahydro-1h-isoindol-4-yl]-2-hydroxy-4-methylhept-6-en-3-one)