NP-MRD: Showing NP-Card for 7-deacetyl-7-benzoylgedunin (NP0250341)

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Record Information

Version

2.0

Created at

2022-09-07 13:08:21 UTC

Updated at

2022-09-07 13:08:21 UTC

NP-MRD ID

NP0250341

Secondary Accession Numbers

None

Natural Product Identification

Common Name

7-deacetyl-7-benzoylgedunin

Description

7-Deacetyl-7-benzoylgedunin belongs to the class of organic compounds known as limonoids. These are highly oxygenated, modified terpenoids with a prototypical structure either containing or derived from a precursor with a 4,4,8-trimethyl-17-furanylsteroid skeleton. All naturally occurring citrus limonoids contain a furan ring attached to the D-ring, at C-17, as well as oxygen containing functional groups at C-3, C-4, C-7, C-16 and C-17. 7-deacetyl-7-benzoylgedunin is found in Azadirachta indica. Based on a literature review very few articles have been published on 7-deacetyl-7-benzoylgedunin.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309072215082D          

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M  END

     RDKit          3D

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M  END


  Mrv1652309072215082D          

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   -0.6310   -2.2112    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6150   -1.3863    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0957    0.2566    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1744    1.0361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3657    1.6598    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9845    1.1921    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7946    1.3480    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5246    0.5684    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  1  0  0  0
  8 10  1  0  0  0  0
  2 10  1  0  0  0  0
 10 11  1  1  0  0  0
 11 12  1  0  0  0  0
 12 13  1  6  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 16 21  1  0  0  0  0
 12 22  1  0  0  0  0
 22 23  1  1  0  0  0
 22 24  1  0  0  0  0
  8 24  1  0  0  0  0
 24 25  1  1  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  6  0  0  0
 27 29  1  0  0  0  0
 29 30  1  6  0  0  0
 30 31  1  0  0  0  0
 31 32  2  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 30 34  2  0  0  0  0
 29 35  1  0  0  0  0
 35 36  1  0  0  0  0
 36 37  2  0  0  0  0
 36 38  1  0  0  0  0
 38 39  1  1  0  0  0
 40 39  1  1  0  0  0
 38 40  1  0  0  0  0
 27 40  1  0  0  0  0
 22 40  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0250341

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1(C)[C@@H]2C[C@@H](OC(=O)C3=CC=CC=C3)[C@]3(C)[C@H](CC[C@@]4(C)[C@@H](OC(=O)[C@H]5O[C@@]345)C3=COC=C3)[C@@]2(C)C=CC1=O

> <INCHI_IDENTIFIER>
InChI=1S/C33H36O7/c1-29(2)22-17-24(38-27(35)19-9-7-6-8-10-19)32(5)21(30(22,3)14-12-23(29)34)11-15-31(4)25(20-13-16-37-18-20)39-28(36)26-33(31,32)40-26/h6-10,12-14,16,18,21-22,24-26H,11,15,17H2,1-5H3/t21-,22+,24-,25+,26-,30-,31+,32+,33-/m1/s1

> <INCHI_KEY>
FJGQKVDLYYRRKR-VHSMAHMUSA-N

> <FORMULA>
C33H36O7

> <MOLECULAR_WEIGHT>
544.644

> <EXACT_MASS>
544.246103499

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
76

> <JCHEM_AVERAGE_POLARIZABILITY>
57.23986490699163

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,2R,4S,7R,8S,11R,12R,17R,19R)-7-(furan-3-yl)-1,8,12,16,16-pentamethyl-5,15-dioxo-3,6-dioxapentacyclo[9.8.0.0^{2,4}.0^{2,8}.0^{12,17}]nonadec-13-en-19-yl benzoate

> <JCHEM_LOGP>
6.354158751333333

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-2.869808689334488

> <JCHEM_POLAR_SURFACE_AREA>
95.34

> <JCHEM_REFRACTIVITY>
145.66350000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2R,4S,7R,8S,11R,12R,17R,19R)-7-(furan-3-yl)-1,8,12,16,16-pentamethyl-5,15-dioxo-3,6-dioxapentacyclo[9.8.0.0^{2,4}.0^{2,8}.0^{12,17}]nonadec-13-en-19-yl benzoate

> <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      10.216   3.016   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.895   2.225   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.346   3.664   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.903   1.061   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      11.415   1.352   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       9.399  -0.394   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.887  -0.685   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.879   0.479   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.375  -0.976   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.383   1.934   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.375   3.098   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.862   2.807   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       3.854   3.971   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       4.358   5.427   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       5.870   5.718   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       3.350   6.591   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.838   6.300   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.830   7.464   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.334   8.919   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.846   9.210   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       3.854   8.046   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.358   1.352   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       4.227   2.886   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       5.366   0.188   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       4.862  -1.267   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       3.350  -1.558   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       2.342  -0.394   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       1.838  -1.849   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       0.830  -0.685   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       0.326  -2.140   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       1.206  -3.403   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       0.277  -4.632   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      -1.178  -4.128   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0      -1.148  -2.588   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0      -0.179   0.479   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0       0.326   1.934   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0      -0.683   3.098   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0       1.838   2.225   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0       3.350   2.516   0.000  0.00  0.00           O+0
HETATM   40  C   UNK     0       2.846   1.061   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4   10                                             
CONECT    3    2                                                            
CONECT    4    2    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   10   24                                             
CONECT    9    8                                                            
CONECT   10    8    2   11                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   22                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17   21                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   16                                                       
CONECT   22   12   23   24   40                                             
CONECT   23   22                                                            
CONECT   24   22    8   25                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28   29   40                                             
CONECT   28   27                                                            
CONECT   29   27   30   35                                                  
CONECT   30   29   31   34                                                  
CONECT   31   30   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33   30                                                       
CONECT   35   29   36                                                       
CONECT   36   35   37   38                                                  
CONECT   37   36                                                            
CONECT   38   36   39   40                                                  
CONECT   39   38   40                                                       
CONECT   40   39   38   27   22                                             
MASTER        0    0    0    0    0    0    0    0   40    0   92    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₃H₃₆O₇

Average Mass

544.6440 Da

Monoisotopic Mass

544.24610 Da

IUPAC Name

(1S,2R,4S,7R,8S,11R,12R,17R,19R)-7-(furan-3-yl)-1,8,12,16,16-pentamethyl-5,15-dioxo-3,6-dioxapentacyclo[9.8.0.0^{2,4}.0^{2,8}.0^{12,17}]nonadec-13-en-19-yl benzoate

Traditional Name

(1S,2R,4S,7R,8S,11R,12R,17R,19R)-7-(furan-3-yl)-1,8,12,16,16-pentamethyl-5,15-dioxo-3,6-dioxapentacyclo[9.8.0.0^{2,4}.0^{2,8}.0^{12,17}]nonadec-13-en-19-yl benzoate

CAS Registry Number

Not Available

SMILES

CC1(C)[C@@H]2C[C@@H](OC(=O)C3=CC=CC=C3)[C@]3(C)[C@H](CC[C@@]4(C)[C@@H](OC(=O)[C@H]5O[C@@]345)C3=COC=C3)[C@@]2(C)C=CC1=O

InChI Identifier

InChI=1S/C33H36O7/c1-29(2)22-17-24(38-27(35)19-9-7-6-8-10-19)32(5)21(30(22,3)14-12-23(29)34)11-15-31(4)25(20-13-16-37-18-20)39-28(36)26-33(31,32)40-26/h6-10,12-14,16,18,21-22,24-26H,11,15,17H2,1-5H3/t21-,22+,24-,25+,26-,30-,31+,32+,33-/m1/s1

InChI Key

FJGQKVDLYYRRKR-VHSMAHMUSA-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
Azadirachta indica	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as limonoids. These are highly oxygenated, modified terpenoids with a prototypical structure either containing or derived from a precursor with a 4,4,8-trimethyl-17-furanylsteroid skeleton. All naturally occurring citrus limonoids contain a furan ring attached to the D-ring, at C-17, as well as oxygen containing functional groups at C-3, C-4, C-7, C-16 and C-17.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Triterpenoids

Direct Parent

Limonoids

Alternative Parents

Substituents

Limonoid skeleton
Naphthopyran
Naphthalene
Benzoate ester
Benzoic acid or derivatives
Benzoyl
Delta_valerolactone
Dioxepane
1,4-dioxepane
Cyclohexenone
Delta valerolactone
Dicarboxylic acid or derivatives
Oxane
Pyran
Monocyclic benzene moiety
Benzenoid
Furan
Heteroaromatic compound
Carboxylic acid ester
Cyclic ketone
Lactone
Ketone
Dialkyl ether
Carboxylic acid derivative
Organoheterocyclic compound
Oxacycle
Oxirane
Ether
Organooxygen compound
Organic oxygen compound
Carbonyl group
Organic oxide
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

epoxide (CHEBI:67297 )
enone (CHEBI:67297 )
furans (CHEBI:67297 )
benzoate ester (CHEBI:67297 )
delta-lactone (CHEBI:67297 )
pentacyclic triterpenoid (CHEBI:67297 )
cyclic terpene ketone (CHEBI:67297 )
limonoid (CHEBI:67297 )

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	6.35	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	95.34 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	145.66 m³·mol⁻¹	ChemAxon
Polarizability	57.24 Å³	ChemAxon
Number of Rings	7	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	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

26335456

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

52952112

PDB ID

Not Available

ChEBI ID

67297

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 7-deacetyl-7-benzoylgedunin (NP0250341)

MOL for NP0250341 (7-deacetyl-7-benzoylgedunin)

3D MOL for NP0250341 (7-deacetyl-7-benzoylgedunin)

3D SDF for NP0250341 (7-deacetyl-7-benzoylgedunin)

3D-SDF for NP0250341 (7-deacetyl-7-benzoylgedunin)

PDB for NP0250341 (7-deacetyl-7-benzoylgedunin)

3D PDB for NP0250341 (7-deacetyl-7-benzoylgedunin)

SMILES for NP0250341 (7-deacetyl-7-benzoylgedunin)

INCHI for NP0250341 (7-deacetyl-7-benzoylgedunin)

Structure for NP0250341 (7-deacetyl-7-benzoylgedunin)

3D Structure for NP0250341 (7-deacetyl-7-benzoylgedunin)