NP-MRD: Showing NP-Card for Azadirolic acid (NP0082289)

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Record Information

Version

2.0

Created at

2022-04-29 03:19:56 UTC

Updated at

2022-04-29 03:19:56 UTC

NP-MRD ID

NP0082289

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Azadirolic acid

Description

(4Z)-5-[(1R,2R,7S,8S,9S,10R,14S,15S)-8-(acetyloxy)-9-hydroxy-2,6,6,10,15-pentamethyl-5-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadeca-3,11-dien-14-yl]hex-4-enoic acid belongs to the class of organic compounds known as sesterterpenoids. These are terpenes composed of five consecutive isoprene units. Azadirolic acid is found in Azadirachta indica . Based on a literature review very few articles have been published on (4Z)-5-[(1R,2R,7S,8S,9S,10R,14S,15S)-8-(acetyloxy)-9-hydroxy-2,6,6,10,15-pentamethyl-5-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadeca-3,11-dien-14-yl]hex-4-enoic acid.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304292205192D          

 36 39  0  0  1  0            999 V2000
    2.6190   -0.6539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3387    0.1221    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8705    0.7528    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.6826    0.6076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3340    1.1139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0168    0.6509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7875   -0.1416    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.9629   -0.1684    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.4311   -0.7991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3228   -0.9107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.7493    3.8565    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    3.1220    2.1594    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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  2  1  1  6  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
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  1  9  1  0  0  0  0
  8 10  1  1  0  0  0
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 15 17  1  0  0  0  0
 11 18  1  0  0  0  0
  3 19  1  0  0  0  0
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  2 22  1  0  0  0  0
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 32 33  2  0  0  0  0
 32 34  1  0  0  0  0
 19 35  1  1  0  0  0
  3 36  1  6  0  0  0
M  END

     RDKit          3D

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M  END


  Mrv1652304292205192D          

 36 39  0  0  1  0            999 V2000
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    3.4023    1.3835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  4  8  1  0  0  0  0
  8  9  1  0  0  0  0
  1  9  1  0  0  0  0
  8 10  1  1  0  0  0
  7 11  1  1  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
 11 18  1  0  0  0  0
  3 19  1  0  0  0  0
 19 20  1  0  0  0  0
 21 20  1  1  0  0  0
 21 22  1  0  0  0  0
  2 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 25 27  1  0  0  0  0
 21 27  1  0  0  0  0
 27 28  1  0  0  0  0
 27 29  1  0  0  0  0
 22 30  1  6  0  0  0
 20 31  1  6  0  0  0
 31 32  1  0  0  0  0
 32 33  2  0  0  0  0
 32 34  1  0  0  0  0
 19 35  1  1  0  0  0
  3 36  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0082289

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)O[C@@H]1[C@@H](O)[C@]2(C)[C@H](CC[C@@]3(C)[C@@H](CC=C23)C(\C)=C/CCC(O)=O)[C@@]2(C)C=CC(=O)C(C)(C)[C@@H]12

> <INCHI_IDENTIFIER>
InChI=1S/C30H42O6/c1-17(9-8-10-23(33)34)19-11-12-20-28(19,5)15-13-21-29(6)16-14-22(32)27(3,4)25(29)24(36-18(2)31)26(35)30(20,21)7/h9,12,14,16,19,21,24-26,35H,8,10-11,13,15H2,1-7H3,(H,33,34)/b17-9-/t19-,21+,24-,25+,26+,28-,29+,30-/m0/s1

> <INCHI_KEY>
BRINQTOFCWWSPH-PKFNJFLISA-N

> <FORMULA>
C30H42O6

> <MOLECULAR_WEIGHT>
498.66

> <EXACT_MASS>
498.298139072

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
78

> <JCHEM_AVERAGE_POLARIZABILITY>
55.42806404892606

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(4Z)-5-[(1R,2R,7S,8S,9S,10R,14S,15S)-8-(acetyloxy)-9-hydroxy-2,6,6,10,15-pentamethyl-5-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-3,11-dien-14-yl]hex-4-enoic acid

> <ALOGPS_LOGP>
5.18

> <JCHEM_LOGP>
4.473216481

> <ALOGPS_LOGS>
-5.12

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
13.652090864066103

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.591961539207082

> <JCHEM_PKA_STRONGEST_BASIC>
-3.388375456222894

> <JCHEM_POLAR_SURFACE_AREA>
100.89999999999999

> <JCHEM_REFRACTIVITY>
139.5496

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.80e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(4Z)-5-[(1R,2R,7S,8S,9S,10R,14S,15S)-8-(acetyloxy)-9-hydroxy-2,6,6,10,15-pentamethyl-5-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-3,11-dien-14-yl]hex-4-enoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 29-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-APR-22         0                                  
HETATM    1  C   UNK     0       4.889  -1.221   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.366   0.228   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.358   1.405   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.874   1.134   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.090   2.079   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.365   1.215   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.937  -0.264   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.398  -0.314   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.405  -1.492   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.069  -1.700   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       9.882  -1.480   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       9.302  -2.907   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.776  -3.117   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.196  -4.544   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.141  -5.759   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       7.561  -7.186   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       9.666  -5.549   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      11.407  -1.269   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.835   2.854   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       3.319   3.125   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.326   1.947   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       2.850   0.499   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       1.857  -0.678   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       0.341  -0.407   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -0.182   1.041   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      -1.698   1.312   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       0.810   2.218   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -0.332   3.252   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       1.028   3.743   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       3.373  -0.949   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       2.796   4.573   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       3.789   5.750   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       3.265   7.199   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       5.305   5.479   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0       5.828   4.031   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0       6.351   2.583   0.000  0.00  0.00           C+0
CONECT    1    2    9                                                       
CONECT    2    1    3   22                                                  
CONECT    3    2    4   19   36                                             
CONECT    4    3    5    8                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8   11                                                  
CONECT    8    7    4    9   10                                             
CONECT    9    8    1                                                       
CONECT   10    8                                                            
CONECT   11    7   12   18                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15                                                            
CONECT   18   11                                                            
CONECT   19    3   20   35                                                  
CONECT   20   19   21   31                                                  
CONECT   21   20   22   27                                                  
CONECT   22   21    2   23   30                                             
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   21   28   29                                             
CONECT   28   27                                                            
CONECT   29   27                                                            
CONECT   30   22                                                            
CONECT   31   20   32                                                       
CONECT   32   31   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32                                                            
CONECT   35   19                                                            
CONECT   36    3                                                            
MASTER        0    0    0    0    0    0    0    0   36    0   78    0
END

View in JSmol

Synonyms

Value	Source
(4Z)-5-[(1R,2R,7S,8S,9S,10R,14S,15S)-8-(Acetyloxy)-9-hydroxy-2,6,6,10,15-pentamethyl-5-oxotetracyclo[8.7.0.0,.0,]heptadeca-3,11-dien-14-yl]hex-4-enoate	Generator

Chemical Formula

C₃₀H₄₂O₆

Average Mass

498.6600 Da

Monoisotopic Mass

498.29814 Da

IUPAC Name

(4Z)-5-[(1R,2R,7S,8S,9S,10R,14S,15S)-8-(acetyloxy)-9-hydroxy-2,6,6,10,15-pentamethyl-5-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-3,11-dien-14-yl]hex-4-enoic acid

Traditional Name

(4Z)-5-[(1R,2R,7S,8S,9S,10R,14S,15S)-8-(acetyloxy)-9-hydroxy-2,6,6,10,15-pentamethyl-5-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-3,11-dien-14-yl]hex-4-enoic acid

CAS Registry Number

Not Available

SMILES

CC(=O)O[C@@H]1[C@@H](O)[C@]2(C)[C@H](CC[C@@]3(C)[C@@H](CC=C23)C(\C)=C/CCC(O)=O)[C@@]2(C)C=CC(=O)C(C)(C)[C@@H]12

InChI Identifier

InChI=1S/C30H42O6/c1-17(9-8-10-23(33)34)19-11-12-20-28(19,5)15-13-21-29(6)16-14-22(32)27(3,4)25(29)24(36-18(2)31)26(35)30(20,21)7/h9,12,14,16,19,21,24-26,35H,8,10-11,13,15H2,1-7H3,(H,33,34)/b17-9-/t19-,21+,24-,25+,26+,28-,29+,30-/m0/s1

InChI Key

BRINQTOFCWWSPH-PKFNJFLISA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as sesterterpenoids. These are terpenes composed of five consecutive isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesterterpenoids

Direct Parent

Sesterterpenoids

Alternative Parents

Substituents

Sesterterpenoid
Steroid ester
Steroid acid
3-oxo-5-beta-steroid
7-hydroxysteroid
Oxosteroid
Hydroxysteroid
3-oxosteroid
3-oxo-delta-1-steroid
Steroid
Delta-1-steroid
Medium-chain fatty acid
Cyclohexenone
Hydroxy fatty acid
Fatty acyl
Fatty acid
Unsaturated fatty acid
Dicarboxylic acid or derivatives
Cyclic alcohol
Cyclic ketone
Secondary alcohol
Ketone
Carboxylic acid ester
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic 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	5.18	ALOGPS
logP	4.47	ChemAxon
logS	-5.1	ALOGPS
pKa (Strongest Acidic)	4.59	ChemAxon
pKa (Strongest Basic)	-3.4	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	100.9 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	139.55 m³·mol⁻¹	ChemAxon
Polarizability	55.43 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	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

163057991

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Azadirolic acid (NP0082289)

MOL for NP0082289 (Azadirolic acid)

3D MOL for NP0082289 (Azadirolic acid)

3D SDF for NP0082289 (Azadirolic acid)

3D-SDF for NP0082289 (Azadirolic acid)

PDB for NP0082289 (Azadirolic acid)

3D PDB for NP0082289 (Azadirolic acid)

SMILES for NP0082289 (Azadirolic acid)

INCHI for NP0082289 (Azadirolic acid)

Structure for NP0082289 (Azadirolic acid)

3D Structure for NP0082289 (Azadirolic acid)