NP-MRD: Showing NP-Card for 7-benzoylnimbocinol (NP0208474)

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Record Information

Version

2.0

Created at

2022-09-05 05:29:31 UTC

Updated at

2022-09-05 05:29:31 UTC

NP-MRD ID

NP0208474

Secondary Accession Numbers

None

Natural Product Identification

Common Name

7-benzoylnimbocinol

Description

7-Benzoylnimbocinol 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-benzoylnimbocinol is found in Azadirachta indica. Based on a literature review very few articles have been published on 7-benzoylnimbocinol.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309052207292D          

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M  END

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M  END


  Mrv1652309052207292D          

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  4  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  6  0  0  0
  8 10  1  0  0  0  0
  2 10  1  0  0  0  0
 10 11  1  6  0  0  0
 11 12  1  0  0  0  0
 12 13  1  1  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  6  0  0  0
 22 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 26 28  1  0  0  0  0
 28 29  1  1  0  0  0
 29 30  1  0  0  0  0
 30 31  2  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 29 33  2  0  0  0  0
 28 34  1  0  0  0  0
 24 34  1  0  0  0  0
 34 35  1  1  0  0  0
 34 36  1  0  0  0  0
 36 37  1  0  0  0  0
 38 37  1  6  0  0  0
  8 38  1  0  0  0  0
 22 38  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0208474

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@]12CC[C@@H]3[C@@]4(C)C=CC(=O)C(C)(C)[C@@H]4C[C@@H](OC(=O)C4=CC=CC=C4)[C@@]3(C)C1=CC(=O)[C@H]2C1=COC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C33H36O5/c1-30(2)24-18-27(38-29(36)20-9-7-6-8-10-20)33(5)23(31(24,3)15-12-26(30)35)11-14-32(4)25(33)17-22(34)28(32)21-13-16-37-19-21/h6-10,12-13,15-17,19,23-24,27-28H,11,14,18H2,1-5H3/t23-,24+,27-,28-,31-,32-,33-/m1/s1

> <INCHI_KEY>
BNCQITGVZDTXDN-RCNGYQEYSA-N

> <FORMULA>
C33H36O5

> <MOLECULAR_WEIGHT>
512.646

> <EXACT_MASS>
512.256274259

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
74

> <JCHEM_AVERAGE_POLARIZABILITY>
56.39772867577433

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,2R,7R,9R,10R,14R,15S)-14-(furan-3-yl)-2,6,6,10,15-pentamethyl-5,13-dioxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-3,11-dien-9-yl benzoate

> <JCHEM_LOGP>
6.895412382333334

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.39526477594693

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8766107333545055

> <JCHEM_POLAR_SURFACE_AREA>
73.58000000000001

> <JCHEM_REFRACTIVITY>
146.72000000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2R,7R,9R,10R,14R,15S)-14-(furan-3-yl)-2,6,6,10,15-pentamethyl-5,13-dioxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-3,11-dien-9-yl benzoate

> <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       3.480   0.682   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.811  -0.092   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.342   1.354   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.819  -1.269   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       2.303  -0.998   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       4.342  -2.717   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.858  -2.988   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.851  -1.811   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.374  -3.259   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.327  -0.363   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.320   0.815   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.836   0.544   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       9.829   1.721   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       9.306   3.169   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       7.790   3.440   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      10.298   4.347   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       9.775   5.795   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      10.768   6.972   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      12.284   6.701   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      12.807   5.253   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      11.814   4.076   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       9.359  -0.905   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      10.352   0.273   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      10.875  -1.176   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      12.091  -0.231   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      13.366  -1.095   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      14.814  -0.572   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      12.938  -2.574   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      13.883  -3.790   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      15.422  -3.740   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      15.945  -5.188   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      14.730  -6.134   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0      13.455  -5.269   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      11.399  -2.624   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      12.070  -4.010   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      10.406  -3.802   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       8.890  -3.531   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       8.367  -2.082   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   38                                             
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   38                                             
CONECT   23   22                                                            
CONECT   24   22   25   34                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   29   34                                                  
CONECT   29   28   30   33                                                  
CONECT   30   29   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   29                                                       
CONECT   34   28   24   35   36                                             
CONECT   35   34                                                            
CONECT   36   34   37                                                       
CONECT   37   36   38                                                       
CONECT   38   37    8   22                                                  
MASTER        0    0    0    0    0    0    0    0   38    0   86    0
END

View in JSmol

Synonyms

Value	Source
7-Desacetyl-7-benzoylazadiradione	ChEBI

Chemical Formula

C₃₃H₃₆O₅

Average Mass

512.6460 Da

Monoisotopic Mass

512.25627 Da

IUPAC Name

(1R,2R,7R,9R,10R,14R,15S)-14-(furan-3-yl)-2,6,6,10,15-pentamethyl-5,13-dioxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-3,11-dien-9-yl benzoate

Traditional Name

(1R,2R,7R,9R,10R,14R,15S)-14-(furan-3-yl)-2,6,6,10,15-pentamethyl-5,13-dioxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-3,11-dien-9-yl benzoate

CAS Registry Number

Not Available

SMILES

C[C@@]12CC[C@@H]3[C@@]4(C)C=CC(=O)C(C)(C)[C@@H]4C[C@@H](OC(=O)C4=CC=CC=C4)[C@@]3(C)C1=CC(=O)[C@H]2C1=COC=C1

InChI Identifier

InChI=1S/C33H36O5/c1-30(2)24-18-27(38-29(36)20-9-7-6-8-10-20)33(5)23(31(24,3)15-12-26(30)35)11-14-32(4)25(33)17-22(34)28(32)21-13-16-37-19-21/h6-10,12-13,15-17,19,23-24,27-28H,11,14,18H2,1-5H3/t23-,24+,27-,28-,31-,32-,33-/m1/s1

InChI Key

BNCQITGVZDTXDN-RCNGYQEYSA-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
17-furanylsteroid skeleton
3-oxo-delta-1-steroid
3-oxosteroid
3-oxo-5-alpha-steroid
Oxosteroid
16-oxosteroid
Delta-1-steroid
Steroid
Benzoate ester
Benzoic acid or derivatives
Benzoyl
Cyclohexenone
Monocyclic benzene moiety
Benzenoid
Furan
Heteroaromatic compound
Cyclic ketone
Ketone
Carboxylic acid ester
Carboxylic acid derivative
Organoheterocyclic compound
Oxacycle
Monocarboxylic acid or derivatives
Organic oxide
Carbonyl group
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

furans (CHEBI:67282 )
benzoate ester (CHEBI:67282 )
tetracyclic triterpenoid (CHEBI:67282 )
cyclic terpene ketone (CHEBI:67282 )
limonoid (CHEBI:67282 )

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	6.9	ChemAxon
pKa (Strongest Acidic)	14.4	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	73.58 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	146.72 m³·mol⁻¹	ChemAxon
Polarizability	56.4 Å³	ChemAxon
Number of Rings	6	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

26347220

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

54580354

PDB ID

Not Available

ChEBI ID

67282

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 7-benzoylnimbocinol (NP0208474)

MOL for NP0208474 (7-benzoylnimbocinol)

3D MOL for NP0208474 (7-benzoylnimbocinol)

3D SDF for NP0208474 (7-benzoylnimbocinol)

3D-SDF for NP0208474 (7-benzoylnimbocinol)

PDB for NP0208474 (7-benzoylnimbocinol)

3D PDB for NP0208474 (7-benzoylnimbocinol)

SMILES for NP0208474 (7-benzoylnimbocinol)

INCHI for NP0208474 (7-benzoylnimbocinol)

Structure for NP0208474 (7-benzoylnimbocinol)

3D Structure for NP0208474 (7-benzoylnimbocinol)