NP-MRD: Showing NP-Card for 5-benzyl-2-(5,6-dihydroxy-4-methylhept-1-en-1-yl)-6,6a-dimethyl-1ah,2h,5h,5ah,6h-oxireno[2,3-f]isoindole-2a,3-diol (NP0249764)

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Record Information

Version

2.0

Created at

2022-09-07 12:25:14 UTC

Updated at

2022-09-07 12:25:15 UTC

NP-MRD ID

NP0249764

Secondary Accession Numbers

None

Natural Product Identification

Common Name

5-benzyl-2-(5,6-dihydroxy-4-methylhept-1-en-1-yl)-6,6a-dimethyl-1ah,2h,5h,5ah,6h-oxireno[2,3-f]isoindole-2a,3-diol

Description

5-Benzyl-2-(5,6-dihydroxy-4-methylhept-1-en-1-yl)-6,6a-dimethyl-1aH,2H,2aH,5H,5aH,6H,6aH-oxireno[2,3-f]isoindole-2a,3-diol belongs to the class of organic compounds known as isoindolones. These are aromatic polycyclic compounds that an isoindole bearing a ketone. 5-benzyl-2-(5,6-dihydroxy-4-methylhept-1-en-1-yl)-6,6a-dimethyl-1ah,2h,5h,5ah,6h-oxireno[2,3-f]isoindole-2a,3-diol is found in Mariannaea elegans. Based on a literature review very few articles have been published on 5-benzyl-2-(5,6-dihydroxy-4-methylhept-1-en-1-yl)-6,6a-dimethyl-1aH,2H,2aH,5H,5aH,6H,6aH-oxireno[2,3-f]isoindole-2a,3-diol.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309072214252D          

 31 34  0  0  0  0            999 V2000
    5.4223    5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4223    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1368    4.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7079    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7079    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4223    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7079    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4059   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789   -0.4125    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


  Mrv1652309072214252D          

 31 34  0  0  0  0            999 V2000
    5.4223    5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END
> <DATABASE_ID>
NP0249764

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(O)C(O)C(C)CC=CC1C2OC2(C)C(C)C2C(CC3=CC=CC=C3)N=C(O)C12O

> <INCHI_IDENTIFIER>
InChI=1S/C25H35NO5/c1-14(21(28)16(3)27)9-8-12-18-22-24(4,31-22)15(2)20-19(26-23(29)25(18,20)30)13-17-10-6-5-7-11-17/h5-8,10-12,14-16,18-22,27-28,30H,9,13H2,1-4H3,(H,26,29)

> <INCHI_KEY>
PYBCICUBSSPZBO-UHFFFAOYSA-N

> <FORMULA>
C25H35NO5

> <MOLECULAR_WEIGHT>
429.557

> <EXACT_MASS>
429.251523231

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
66

> <JCHEM_AVERAGE_POLARIZABILITY>
48.75032746621504

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5-benzyl-2-(5,6-dihydroxy-4-methylhept-1-en-1-yl)-6,6a-dimethyl-1aH,2H,2aH,5H,5aH,6H,6aH-oxireno[2,3-f]isoindole-2a,3-diol

> <JCHEM_LOGP>
1.4700142401740113

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.299575619680713

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.0320686175698697

> <JCHEM_PKA_STRONGEST_BASIC>
4.74067794973806

> <JCHEM_POLAR_SURFACE_AREA>
105.81

> <JCHEM_REFRACTIVITY>
119.02420000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
5-benzyl-2-(5,6-dihydroxy-4-methylhept-1-en-1-yl)-6,6a-dimethyl-1aH,2H,5H,5aH,6H-oxireno[2,3-f]isoindole-2a,3-diol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 07-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-SEP-22         0                                  
HETATM    1  C   UNK     0      10.122  10.780   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      10.122   9.240   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      11.455   8.470   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       8.788   8.470   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       7.454   9.240   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       8.788   6.930   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      10.122   6.160   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.454   6.160   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.454   4.620   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.121   3.850   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.121   2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.454   1.540   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       8.788   0.770   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       7.454   0.000   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.224  -1.334   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.121  -0.770   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.121  -2.310   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.787   0.000   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.322  -0.476   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.846  -1.941   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       1.340  -2.261   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       0.864  -3.725   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -0.642  -4.046   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -1.673  -2.901   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -1.197  -1.436   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       0.310  -1.116   0.000  0.00  0.00           C+0
HETATM   27  N   UNK     0       2.417   0.770   0.000  0.00  0.00           N+0
HETATM   28  C   UNK     0       3.322   2.016   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       2.846   3.481   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       4.787   1.540   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       4.626   3.072   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   30                                                  
CONECT   12   11   13   14                                                  
CONECT   13   12   14                                                       
CONECT   14   13   12   15   16                                             
CONECT   15   14                                                            
CONECT   16   14   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19   30                                                  
CONECT   19   18   20   27                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22   26                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   21                                                       
CONECT   27   19   28                                                       
CONECT   28   27   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   11   18   31                                             
CONECT   31   30                                                            
MASTER        0    0    0    0    0    0    0    0   31    0   68    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₅H₃₅NO₅

Average Mass

429.5570 Da

Monoisotopic Mass

429.25152 Da

IUPAC Name

5-benzyl-2-(5,6-dihydroxy-4-methylhept-1-en-1-yl)-6,6a-dimethyl-1aH,2H,2aH,5H,5aH,6H,6aH-oxireno[2,3-f]isoindole-2a,3-diol

Traditional Name

5-benzyl-2-(5,6-dihydroxy-4-methylhept-1-en-1-yl)-6,6a-dimethyl-1aH,2H,5H,5aH,6H-oxireno[2,3-f]isoindole-2a,3-diol

CAS Registry Number

Not Available

SMILES

CC(O)C(O)C(C)CC=CC1C2OC2(C)C(C)C2C(CC3=CC=CC=C3)N=C(O)C12O

InChI Identifier

InChI=1S/C25H35NO5/c1-14(21(28)16(3)27)9-8-12-18-22-24(4,31-22)15(2)20-19(26-23(29)25(18,20)30)13-17-10-6-5-7-11-17/h5-8,10-12,14-16,18-22,27-28,30H,9,13H2,1-4H3,(H,26,29)

InChI Key

PYBCICUBSSPZBO-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
Mariannaea elegans	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as isoindolones. These are aromatic polycyclic compounds that an isoindole bearing a ketone.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Isoindoles and derivatives

Sub Class

Isoindolines

Direct Parent

Isoindolones

Alternative Parents

Substituents

Isoindolone
Isoindole
Oxepane
Monocyclic benzene moiety
Pyrrolidone
2-pyrrolidone
Benzenoid
Tertiary alcohol
Cyclic alcohol
Pyrrolidine
Carboxamide group
Secondary carboxylic acid amide
Secondary alcohol
Lactam
Oxacycle
Azacycle
Carboxylic acid derivative
Dialkyl ether
Oxirane
Ether
Organic oxide
Carbonyl group
Hydrocarbon derivative
Alcohol
Organic nitrogen compound
Organic oxygen compound
Organonitrogen compound
Organooxygen compound
Organopnictogen compound
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	1.47	ChemAxon
pKa (Strongest Acidic)	2.03	ChemAxon
pKa (Strongest Basic)	4.74	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	105.81 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	119.02 m³·mol⁻¹	ChemAxon
Polarizability	48.75 Å³	ChemAxon
Number of Rings	4	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

75986799

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 5-benzyl-2-(5,6-dihydroxy-4-methylhept-1-en-1-yl)-6,6a-dimethyl-1ah,2h,5h,5ah,6h-oxireno[2,3-f]isoindole-2a,3-diol (NP0249764)

MOL for NP0249764 (5-benzyl-2-(5,6-dihydroxy-4-methylhept-1-en-1-yl)-6,6a-dimethyl-1ah,2h,5h,5ah,6h-oxireno[2,3-f]isoindole-2a,3-diol)

3D MOL for NP0249764 (5-benzyl-2-(5,6-dihydroxy-4-methylhept-1-en-1-yl)-6,6a-dimethyl-1ah,2h,5h,5ah,6h-oxireno[2,3-f]isoindole-2a,3-diol)

3D SDF for NP0249764 (5-benzyl-2-(5,6-dihydroxy-4-methylhept-1-en-1-yl)-6,6a-dimethyl-1ah,2h,5h,5ah,6h-oxireno[2,3-f]isoindole-2a,3-diol)

3D-SDF for NP0249764 (5-benzyl-2-(5,6-dihydroxy-4-methylhept-1-en-1-yl)-6,6a-dimethyl-1ah,2h,5h,5ah,6h-oxireno[2,3-f]isoindole-2a,3-diol)

PDB for NP0249764 (5-benzyl-2-(5,6-dihydroxy-4-methylhept-1-en-1-yl)-6,6a-dimethyl-1ah,2h,5h,5ah,6h-oxireno[2,3-f]isoindole-2a,3-diol)

3D PDB for NP0249764 (5-benzyl-2-(5,6-dihydroxy-4-methylhept-1-en-1-yl)-6,6a-dimethyl-1ah,2h,5h,5ah,6h-oxireno[2,3-f]isoindole-2a,3-diol)

SMILES for NP0249764 (5-benzyl-2-(5,6-dihydroxy-4-methylhept-1-en-1-yl)-6,6a-dimethyl-1ah,2h,5h,5ah,6h-oxireno[2,3-f]isoindole-2a,3-diol)

INCHI for NP0249764 (5-benzyl-2-(5,6-dihydroxy-4-methylhept-1-en-1-yl)-6,6a-dimethyl-1ah,2h,5h,5ah,6h-oxireno[2,3-f]isoindole-2a,3-diol)

Structure for NP0249764 (5-benzyl-2-(5,6-dihydroxy-4-methylhept-1-en-1-yl)-6,6a-dimethyl-1ah,2h,5h,5ah,6h-oxireno[2,3-f]isoindole-2a,3-diol)

3D Structure for NP0249764 (5-benzyl-2-(5,6-dihydroxy-4-methylhept-1-en-1-yl)-6,6a-dimethyl-1ah,2h,5h,5ah,6h-oxireno[2,3-f]isoindole-2a,3-diol)