NP-MRD: Showing NP-Card for (1r,3br,4r,5ar,9ar,9br,11as)-3b,6,6,9a,11a-pentamethyl-2,7-dioxo-1-(2-oxo-5h-furan-3-yl)-1h,4h,5h,5ah,9bh,10h,11h-cyclopenta[a]phenanthren-4-yl acetate (NP0321643)

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Record Information

Version

2.0

Created at

2022-09-11 23:57:35 UTC

Updated at

2022-09-11 23:57:35 UTC

NP-MRD ID

NP0321643

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r,3br,4r,5ar,9ar,9br,11as)-3b,6,6,9a,11a-pentamethyl-2,7-dioxo-1-(2-oxo-5h-furan-3-yl)-1h,4h,5h,5ah,9bh,10h,11h-cyclopenta[a]phenanthren-4-yl acetate

Description

AZADIRADIONOLIDE 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. (1r,3br,4r,5ar,9ar,9br,11as)-3b,6,6,9a,11a-pentamethyl-2,7-dioxo-1-(2-oxo-5h-furan-3-yl)-1h,4h,5h,5ah,9bh,10h,11h-cyclopenta[a]phenanthren-4-yl acetate is found in Azadirachta indica. (1r,3br,4r,5ar,9ar,9br,11as)-3b,6,6,9a,11a-pentamethyl-2,7-dioxo-1-(2-oxo-5h-furan-3-yl)-1h,4h,5h,5ah,9bh,10h,11h-cyclopenta[a]phenanthren-4-yl acetate was first documented in 1999 (PMID: 10425127). Based on a literature review very few articles have been published on AZADIRADIONOLIDE.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309122201572D          

 34 38  0  0  1  0            999 V2000
    3.3736   -5.2160    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


  Mrv1652309122201572D          

 34 38  0  0  1  0            999 V2000
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 20 26  1  0  0  0  0
 26 27  1  6  0  0  0
 27 28  2  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 27 31  1  0  0  0  0
 31 32  2  0  0  0  0
 22 33  1  0  0  0  0
  5 33  1  0  0  0  0
 17 33  1  0  0  0  0
 33 34  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0321643

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)O[C@@H]1C[C@H]2C(C)(C)C(=O)C=C[C@]2(C)[C@H]2CC[C@@]3(C)[C@@H](C(=O)C=C3[C@]12C)C1=CCOC1=O

> <INCHI_IDENTIFIER>
InChI=1S/C28H34O6/c1-15(29)34-22-14-19-25(2,3)21(31)8-11-26(19,4)18-7-10-27(5)20(28(18,22)6)13-17(30)23(27)16-9-12-33-24(16)32/h8-9,11,13,18-19,22-23H,7,10,12,14H2,1-6H3/t18-,19+,22-,23-,26-,27-,28-/m1/s1

> <INCHI_KEY>
ANQXYDNAHFDKKH-ZWERPURDSA-N

> <FORMULA>
C28H34O6

> <MOLECULAR_WEIGHT>
466.574

> <EXACT_MASS>
466.235538815

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
68

> <JCHEM_AVERAGE_POLARIZABILITY>
50.23504839547235

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <JCHEM_LOGP>
4.146491296333334

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
16.267231396530864

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.146178752553674

> <JCHEM_PKA_STRONGEST_BASIC>
-4.9260598369522155

> <JCHEM_POLAR_SURFACE_AREA>
86.74000000000001

> <JCHEM_REFRACTIVITY>
128.04139999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

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

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 12-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-SEP-22         0                                  
HETATM    1  C   UNK     0       6.297  -9.737   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.305  -8.559   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       3.789  -8.830   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       5.828  -7.111   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       4.835  -5.934   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.319  -6.205   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.326  -5.027   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.810  -5.298   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.341  -6.744   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.521  -6.072   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.182  -4.121   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -1.698  -4.392   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       0.341  -2.673   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.857  -2.402   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.850  -3.579   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.373  -2.131   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.366  -3.308   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.889  -1.859   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.405  -1.588   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       7.398  -2.766   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       8.069  -1.380   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       6.874  -4.214   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       8.090  -5.159   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       9.365  -4.295   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      10.813  -4.818   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       8.937  -2.816   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       9.882  -1.600   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       9.454  -0.121   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      10.728   0.744   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      11.944  -0.202   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      11.421  -1.650   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      12.285  -2.925   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       5.358  -4.485   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       6.351  -5.663   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6   33                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   15                                                  
CONECT    8    7    9   10   11                                             
CONECT    9    8                                                            
CONECT   10    8                                                            
CONECT   11    8   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14    7   16   17                                             
CONECT   16   15                                                            
CONECT   17   15   18   33                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21   22   26                                             
CONECT   21   20                                                            
CONECT   22   20   23   33                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   20   27                                                  
CONECT   27   26   28   31                                                  
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   27   32                                                  
CONECT   32   31                                                            
CONECT   33   22    5   17   34                                             
CONECT   34   33                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   76    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₈H₃₄O₆

Average Mass

466.5740 Da

Monoisotopic Mass

466.23554 Da

IUPAC Name

(1R,2R,7R,9R,10R,14R,15S)-2,6,6,10,15-pentamethyl-5,13-dioxo-14-(2-oxo-2,5-dihydrofuran-3-yl)tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-3,11-dien-9-yl acetate

Traditional Name

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

CAS Registry Number

Not Available

SMILES

CC(=O)O[C@@H]1C[C@H]2C(C)(C)C(=O)C=C[C@]2(C)[C@H]2CC[C@@]3(C)[C@@H](C(=O)C=C3[C@]12C)C1=CCOC1=O

InChI Identifier

InChI=1S/C28H34O6/c1-15(29)34-22-14-19-25(2,3)21(31)8-11-26(19,4)18-7-10-27(5)20(28(18,22)6)13-17(30)23(27)16-9-12-33-24(16)32/h8-9,11,13,18-19,22-23H,7,10,12,14H2,1-6H3/t18-,19+,22-,23-,26-,27-,28-/m1/s1

InChI Key

ANQXYDNAHFDKKH-ZWERPURDSA-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
Steroid lactone
Steroid ester
3-oxo-delta-1-steroid
3-oxosteroid
16-oxosteroid
Oxosteroid
3-oxo-5-alpha-steroid
Delta-1-steroid
Steroid
Cyclohexenone
2-furanone
Dicarboxylic acid or derivatives
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Dihydrofuran
Cyclic ketone
Lactone
Ketone
Carboxylic acid ester
Organoheterocyclic compound
Oxacycle
Carboxylic acid derivative
Organic oxide
Organic oxygen compound
Carbonyl group
Organooxygen compound
Hydrocarbon derivative
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
logP	4.15	ChemAxon
pKa (Strongest Acidic)	13.15	ChemAxon
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	86.74 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	128.04 m³·mol⁻¹	ChemAxon
Polarizability	50.24 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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

C00049626

Chemspider ID

9973098

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11798426

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Siddiqui BS, Ghiasuddin G, Faizi S, Rasheed M: Triterpenoids of the fruit coats of azadirachta indica. J Nat Prod. 1999 Jul;62(7):1006-9. doi: 10.1021/np980177v. [PubMed:10425127 ]
LOTUS database [Link]

Showing NP-Card for (1r,3br,4r,5ar,9ar,9br,11as)-3b,6,6,9a,11a-pentamethyl-2,7-dioxo-1-(2-oxo-5h-furan-3-yl)-1h,4h,5h,5ah,9bh,10h,11h-cyclopenta[a]phenanthren-4-yl acetate (NP0321643)

MOL for NP0321643 ((1r,3br,4r,5ar,9ar,9br,11as)-3b,6,6,9a,11a-pentamethyl-2,7-dioxo-1-(2-oxo-5h-furan-3-yl)-1h,4h,5h,5ah,9bh,10h,11h-cyclopenta[a]phenanthren-4-yl acetate)

3D MOL for NP0321643 ((1r,3br,4r,5ar,9ar,9br,11as)-3b,6,6,9a,11a-pentamethyl-2,7-dioxo-1-(2-oxo-5h-furan-3-yl)-1h,4h,5h,5ah,9bh,10h,11h-cyclopenta[a]phenanthren-4-yl acetate)

3D SDF for NP0321643 ((1r,3br,4r,5ar,9ar,9br,11as)-3b,6,6,9a,11a-pentamethyl-2,7-dioxo-1-(2-oxo-5h-furan-3-yl)-1h,4h,5h,5ah,9bh,10h,11h-cyclopenta[a]phenanthren-4-yl acetate)

3D-SDF for NP0321643 ((1r,3br,4r,5ar,9ar,9br,11as)-3b,6,6,9a,11a-pentamethyl-2,7-dioxo-1-(2-oxo-5h-furan-3-yl)-1h,4h,5h,5ah,9bh,10h,11h-cyclopenta[a]phenanthren-4-yl acetate)

PDB for NP0321643 ((1r,3br,4r,5ar,9ar,9br,11as)-3b,6,6,9a,11a-pentamethyl-2,7-dioxo-1-(2-oxo-5h-furan-3-yl)-1h,4h,5h,5ah,9bh,10h,11h-cyclopenta[a]phenanthren-4-yl acetate)

3D PDB for NP0321643 ((1r,3br,4r,5ar,9ar,9br,11as)-3b,6,6,9a,11a-pentamethyl-2,7-dioxo-1-(2-oxo-5h-furan-3-yl)-1h,4h,5h,5ah,9bh,10h,11h-cyclopenta[a]phenanthren-4-yl acetate)

SMILES for NP0321643 ((1r,3br,4r,5ar,9ar,9br,11as)-3b,6,6,9a,11a-pentamethyl-2,7-dioxo-1-(2-oxo-5h-furan-3-yl)-1h,4h,5h,5ah,9bh,10h,11h-cyclopenta[a]phenanthren-4-yl acetate)

INCHI for NP0321643 ((1r,3br,4r,5ar,9ar,9br,11as)-3b,6,6,9a,11a-pentamethyl-2,7-dioxo-1-(2-oxo-5h-furan-3-yl)-1h,4h,5h,5ah,9bh,10h,11h-cyclopenta[a]phenanthren-4-yl acetate)

Structure for NP0321643 ((1r,3br,4r,5ar,9ar,9br,11as)-3b,6,6,9a,11a-pentamethyl-2,7-dioxo-1-(2-oxo-5h-furan-3-yl)-1h,4h,5h,5ah,9bh,10h,11h-cyclopenta[a]phenanthren-4-yl acetate)

3D Structure for NP0321643 ((1r,3br,4r,5ar,9ar,9br,11as)-3b,6,6,9a,11a-pentamethyl-2,7-dioxo-1-(2-oxo-5h-furan-3-yl)-1h,4h,5h,5ah,9bh,10h,11h-cyclopenta[a]phenanthren-4-yl acetate)