NP-MRD: Showing NP-Card for Nimbidic acid (NP0084255)

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Record Information

Version

2.0

Created at

2022-04-29 05:02:47 UTC

Updated at

2022-04-29 05:02:48 UTC

NP-MRD ID

NP0084255

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Nimbidic acid

Description

Salannic acid, also known as salannate, 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. Nimbidic acid is found in Azadirachta indica . Based on a literature review very few articles have been published on Salannic acid.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304292207022D          

 38 43  0  0  1  0            999 V2000
    2.1354   -2.3323    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2305   -1.5128    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
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    3.7738    0.7363    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5611   -0.5052    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.3183   -0.1778    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    6.3200    0.7046    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    5.1966   -1.0313    0.0000 H   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


  Mrv1652304292207022D          

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 28 29  1  0  0  0  0
 29 30  1  6  0  0  0
 29 31  1  0  0  0  0
 31 32  1  1  0  0  0
 31 33  1  0  0  0  0
 24 33  1  0  0  0  0
 33 34  1  6  0  0  0
 33 35  1  0  0  0  0
  2 35  1  0  0  0  0
 35 36  1  1  0  0  0
 35 37  1  0  0  0  0
 37 38  1  0  0  0  0
 31 38  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0084255

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@@]12C[C@]([H])(C(C)=C1[C@@]1(C)[C@H](CC(O)=O)[C@@]3(C)[C@@H](O)C[C@@H](O)[C@@]4(C)CO[C@@]([H])([C@@]1([H])O2)[C@]34[H])C1=COC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C26H34O7/c1-12-14(13-5-6-31-10-13)7-15-20(12)26(4)16(8-19(29)30)25(3)18(28)9-17(27)24(2)11-32-21(22(24)25)23(26)33-15/h5-6,10,14-18,21-23,27-28H,7-9,11H2,1-4H3,(H,29,30)/t14-,15-,16-,17-,18+,21-,22+,23-,24-,25+,26-/m1/s1

> <INCHI_KEY>
QMEMRUDWBPMCGJ-SRSHEJQUSA-N

> <FORMULA>
C26H34O7

> <MOLECULAR_WEIGHT>
458.551

> <EXACT_MASS>
458.230453435

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
67

> <JCHEM_AVERAGE_POLARIZABILITY>
47.86774969225155

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-[(1R,2S,4R,6R,9R,10R,11R,12S,14R,15R,18R)-6-(furan-3-yl)-12,14-dihydroxy-7,9,11,15-tetramethyl-3,17-dioxapentacyclo[9.6.1.0^{2,9}.0^{4,8}.0^{15,18}]octadec-7-en-10-yl]acetic acid

> <ALOGPS_LOGP>
2.30

> <JCHEM_LOGP>
1.1578845643333326

> <ALOGPS_LOGS>
-3.30

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
14.270886818873247

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.745737608097144

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8388357459468385

> <JCHEM_POLAR_SURFACE_AREA>
109.36000000000001

> <JCHEM_REFRACTIVITY>
118.33630000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.31e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[(1R,2S,4R,6R,9R,10R,11R,12S,14R,15R,18R)-6-(furan-3-yl)-12,14-dihydroxy-7,9,11,15-tetramethyl-3,17-dioxapentacyclo[9.6.1.0^{2,9}.0^{4,8}.0^{15,18}]octadec-7-en-10-yl]acetic 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  H   UNK     0       3.986  -4.354   0.000  0.00  0.00           H+0
HETATM    2  C   UNK     0       4.164  -2.824   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.500  -1.321   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.033  -1.177   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.189  -0.159   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.044   1.375   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.514  -0.943   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.928  -0.332   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      10.264   1.171   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      11.797   1.315   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      12.408  -0.098   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      11.253  -1.116   0.000  0.00  0.00           C+0
HETATM   13  H   UNK     0       9.700  -1.925   0.000  0.00  0.00           H+0
HETATM   14  C   UNK     0       8.178  -2.446   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.644  -2.590   0.000  0.00  0.00           C+0
HETATM   16  H   UNK     0       7.255  -4.004   0.000  0.00  0.00           H+0
HETATM   17  O   UNK     0       5.489  -3.608   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       4.992   0.138   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.367  -0.278   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       3.703   1.224   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.570   2.267   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       1.100   1.807   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       2.906   3.770   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       1.897  -0.738   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       2.020   0.797   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       0.252   0.083   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       0.214   1.623   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      -1.090  -0.672   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -1.107  -2.212   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      -2.449  -2.968   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       0.219  -2.997   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -1.037  -3.888   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       1.561  -2.241   0.000  0.00  0.00           C+0
HETATM   34  H   UNK     0       0.325  -1.323   0.000  0.00  0.00           H+0
HETATM   35  C   UNK     0       2.694  -3.284   0.000  0.00  0.00           C+0
HETATM   36  H   UNK     0       3.030  -1.781   0.000  0.00  0.00           H+0
HETATM   37  O   UNK     0       2.052  -4.684   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0       0.523  -4.506   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   17   35                                             
CONECT    3    2    4   18   19                                             
CONECT    4    3    5   15                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8   13   14                                             
CONECT    8    7    9   12                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11    8                                                       
CONECT   13    7                                                            
CONECT   14    7   15                                                       
CONECT   15   14    4   16   17                                             
CONECT   16   15                                                            
CONECT   17   15    2                                                       
CONECT   18    3                                                            
CONECT   19    3   20   24                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21                                                            
CONECT   24   19   25   26   33                                             
CONECT   25   24                                                            
CONECT   26   24   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   29                                                       
CONECT   29   28   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   32   33   38                                             
CONECT   32   31                                                            
CONECT   33   31   24   34   35                                             
CONECT   34   33                                                            
CONECT   35   33    2   36   37                                             
CONECT   36   35                                                            
CONECT   37   35   38                                                       
CONECT   38   37   31                                                       
MASTER        0    0    0    0    0    0    0    0   38    0   86    0
END

View in JSmol

Synonyms

Value	Source
Salannate	Generator

Chemical Formula

C₂₆H₃₄O₇

Average Mass

458.5510 Da

Monoisotopic Mass

458.23045 Da

IUPAC Name

2-[(1R,2S,4R,6R,9R,10R,11R,12S,14R,15R,18R)-6-(furan-3-yl)-12,14-dihydroxy-7,9,11,15-tetramethyl-3,17-dioxapentacyclo[9.6.1.0^{2,9}.0^{4,8}.0^{15,18}]octadec-7-en-10-yl]acetic acid

Traditional Name

[(1R,2S,4R,6R,9R,10R,11R,12S,14R,15R,18R)-6-(furan-3-yl)-12,14-dihydroxy-7,9,11,15-tetramethyl-3,17-dioxapentacyclo[9.6.1.0^{2,9}.0^{4,8}.0^{15,18}]octadec-7-en-10-yl]acetic acid

CAS Registry Number

Not Available

SMILES

[H][C@@]12C[C@]([H])(C(C)=C1[C@@]1(C)[C@H](CC(O)=O)[C@@]3(C)[C@@H](O)C[C@@H](O)[C@@]4(C)CO[C@@]([H])([C@@]1([H])O2)[C@]34[H])C1=COC=C1

InChI Identifier

InChI=1S/C26H34O7/c1-12-14(13-5-6-31-10-13)7-15-20(12)26(4)16(8-19(29)30)25(3)18(28)9-17(27)24(2)11-32-21(22(24)25)23(26)33-15/h5-6,10,14-18,21-23,27-28H,7-9,11H2,1-4H3,(H,29,30)/t14-,15-,16-,17-,18+,21-,22+,23-,24-,25+,26-/m1/s1

InChI Key

QMEMRUDWBPMCGJ-SRSHEJQUSA-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 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
Naphthofuran
Cyclic alcohol
Furan
Heteroaromatic compound
Tetrahydrofuran
Secondary alcohol
Carboxylic acid derivative
Carboxylic acid
Dialkyl ether
Ether
Monocarboxylic acid or derivatives
Oxacycle
Organoheterocyclic compound
Alcohol
Organic oxide
Hydrocarbon derivative
Organic oxygen compound
Organooxygen compound
Carbonyl group
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	2.3	ALOGPS
logP	1.16	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Acidic)	4.75	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	109.36 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	118.34 m³·mol⁻¹	ChemAxon
Polarizability	47.87 Å³	ChemAxon
Number of Rings	6	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

C00053552

Chemspider ID

161438

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

185704

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for Nimbidic acid (NP0084255)

MOL for NP0084255 (Nimbidic acid)

3D MOL for NP0084255 (Nimbidic acid)

3D SDF for NP0084255 (Nimbidic acid)

3D-SDF for NP0084255 (Nimbidic acid)

PDB for NP0084255 (Nimbidic acid)

3D PDB for NP0084255 (Nimbidic acid)

SMILES for NP0084255 (Nimbidic acid)

INCHI for NP0084255 (Nimbidic acid)

Structure for NP0084255 (Nimbidic acid)

3D Structure for NP0084255 (Nimbidic acid)