NP-MRD: Showing NP-Card for Nomilinic acid (NP0078031)

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Record Information

Version

2.0

Created at

2022-04-28 23:10:17 UTC

Updated at

2022-04-28 23:10:17 UTC

NP-MRD ID

NP0078031

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Nomilinic acid

Description

(3R)-3-(acetyloxy)-3-[(1R,2R,5R,6S,7R,10S,11R,14S)-11-(furan-3-yl)-5-(2-hydroxypropan-2-yl)-2,6,10-trimethyl-3,13-dioxo-12,15-dioxatetracyclo[8.5.0.0¹,¹⁴.0²,⁷]Pentadecan-6-yl]propanoic acid belongs to the class of organic compounds known as steroid lactones. These are sterol lipids containing a lactone moiety linked to the steroid skeleton. Nomilinic acid is found in Citrus limon , Citrus medica, Citrus paradisi L. , Citrus sudachi , Ciyrus aurantium and Ciyrus junos. Based on a literature review very few articles have been published on (3R)-3-(acetyloxy)-3-[(1R,2R,5R,6S,7R,10S,11R,14S)-11-(furan-3-yl)-5-(2-hydroxypropan-2-yl)-2,6,10-trimethyl-3,13-dioxo-12,15-dioxatetracyclo[8.5.0.0¹,¹⁴.0²,⁷]Pentadecan-6-yl]propanoic acid.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304292201102D          

 38 42  0  0  1  0            999 V2000
    1.1270    1.1270    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5395    0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1270   -0.3020    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3020   -0.3020    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1105    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1105    1.8414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1105   -1.0164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9310   -1.1027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1025   -1.9096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3881   -2.3221    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2250   -1.7701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  1  6  1  0  0  0  0
  6  7  2  0  0  0  0
  4  8  1  6  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
  8 12  2  0  0  0  0
  3 13  1  0  0  0  0
 13 14  1  0  0  0  0
 15 14  1  1  0  0  0
 15 16  1  0  0  0  0
  2 16  1  0  0  0  0
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 17 18  2  0  0  0  0
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 21 31  1  6  0  0  0
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 32 33  1  0  0  0  0
 32 34  1  0  0  0  0
 32 35  1  0  0  0  0
 16 36  1  1  0  0  0
  3 37  1  6  0  0  0
  2 38  1  1  0  0  0
  1 38  1  1  0  0  0
M  END

     RDKit          3D

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M  END


  Mrv1652304292201102D          

 38 42  0  0  1  0            999 V2000
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    2.4507    1.2330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.0164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9520    1.1270    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  1  6  1  0  0  0  0
  6  7  2  0  0  0  0
  4  8  1  6  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
  8 12  2  0  0  0  0
  3 13  1  0  0  0  0
 13 14  1  0  0  0  0
 15 14  1  1  0  0  0
 15 16  1  0  0  0  0
  2 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 15 21  1  0  0  0  0
 21 22  1  1  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 24 26  1  0  0  0  0
 22 27  1  1  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 28 30  1  0  0  0  0
 21 31  1  6  0  0  0
 20 32  1  1  0  0  0
 32 33  1  0  0  0  0
 32 34  1  0  0  0  0
 32 35  1  0  0  0  0
 16 36  1  1  0  0  0
  3 37  1  6  0  0  0
  2 38  1  1  0  0  0
  1 38  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0078031

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)O[C@H](CC(O)=O)[C@]1(C)[C@@H](CC(=O)[C@]2(C)[C@@H]1CC[C@@]1(C)[C@@H](OC(=O)[C@H]3O[C@@]213)C1=COC=C1)C(C)(C)O

> <INCHI_IDENTIFIER>
InChI=1S/C28H36O10/c1-14(29)36-19(12-20(31)32)26(5)16-7-9-25(4)21(15-8-10-35-13-15)37-23(33)22-28(25,38-22)27(16,6)18(30)11-17(26)24(2,3)34/h8,10,13,16-17,19,21-22,34H,7,9,11-12H2,1-6H3,(H,31,32)/t16-,17+,19-,21+,22-,25+,26+,27+,28-/m1/s1

> <INCHI_KEY>
ZIKZPLSIAVHITA-FNCGWBFLSA-N

> <FORMULA>
C28H36O10

> <MOLECULAR_WEIGHT>
532.586

> <EXACT_MASS>
532.230847359

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
74

> <JCHEM_AVERAGE_POLARIZABILITY>
54.19584488587882

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(3R)-3-(acetyloxy)-3-[(1R,2R,5R,6S,7R,10S,11R,14S)-11-(furan-3-yl)-5-(2-hydroxypropan-2-yl)-2,6,10-trimethyl-3,13-dioxo-12,15-dioxatetracyclo[8.5.0.0^{1,14}.0^{2,7}]pentadecan-6-yl]propanoic acid

> <ALOGPS_LOGP>
2.81

> <JCHEM_LOGP>
2.3529130109999996

> <ALOGPS_LOGS>
-3.88

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
15.024417643214168

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.1006866569721065

> <JCHEM_PKA_STRONGEST_BASIC>
-2.7854874609257863

> <JCHEM_POLAR_SURFACE_AREA>
149.57

> <JCHEM_REFRACTIVITY>
129.0983

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
7.05e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3R)-3-(acetyloxy)-3-[(1R,2R,5R,6S,7R,10S,11R,14S)-11-(furan-3-yl)-5-(2-hydroxypropan-2-yl)-2,6,10-trimethyl-3,13-dioxo-12,15-dioxatetracyclo[8.5.0.0^{1,14}.0^{2,7}]pentadecan-6-yl]propanoic 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       2.104   2.104   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.874   0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.104  -0.564   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.564  -0.564   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      -0.206   0.770   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       0.564   2.104   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -0.206   3.437   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -0.206  -1.897   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.738  -2.058   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -2.058  -3.565   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -0.724  -4.335   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       0.420  -3.304   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.874  -1.897   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.414  -1.897   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.184  -0.564   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.414   0.770   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.184   2.104   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       4.414   3.437   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       6.724   2.104   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       7.494   0.770   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       6.724  -0.564   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       6.777  -2.103   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       8.137  -2.826   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       8.191  -4.365   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       9.551  -5.088   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0       6.885  -5.181   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0       5.471  -2.919   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       5.525  -4.458   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       6.200  -5.842   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       4.219  -5.274   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       8.030  -1.380   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       9.034   0.770   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      10.574   0.770   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       9.034  -0.770   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       9.034   2.310   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       4.575   2.302   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       1.334  -1.897   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0       3.644   2.104   0.000  0.00  0.00           O+0
CONECT    1    2    6   38                                                  
CONECT    2    1    3   16   38                                             
CONECT    3    2    4   13   37                                             
CONECT    4    3    5    8                                                  
CONECT    5    4    6                                                       
CONECT    6    5    1    7                                                  
CONECT    7    6                                                            
CONECT    8    4    9   12                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11    8                                                       
CONECT   13    3   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   21                                                  
CONECT   16   15    2   17   36                                             
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20                                                       
CONECT   20   19   21   32                                                  
CONECT   21   20   15   22   31                                             
CONECT   22   21   23   27                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24                                                            
CONECT   27   22   28                                                       
CONECT   28   27   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28                                                            
CONECT   31   21                                                            
CONECT   32   20   33   34   35                                             
CONECT   33   32                                                            
CONECT   34   32                                                            
CONECT   35   32                                                            
CONECT   36   16                                                            
CONECT   37    3                                                            
CONECT   38    2    1                                                       
MASTER        0    0    0    0    0    0    0    0   38    0   84    0
END

View in JSmol

Synonyms

Value	Source
(3R)-3-(Acetyloxy)-3-[(1R,2R,5R,6S,7R,10S,11R,14S)-11-(furan-3-yl)-5-(2-hydroxypropan-2-yl)-2,6,10-trimethyl-3,13-dioxo-12,15-dioxatetracyclo[8.5.0.0,.0,]pentadecan-6-yl]propanoate	Generator

Chemical Formula

C₂₈H₃₆O₁₀

Average Mass

532.5860 Da

Monoisotopic Mass

532.23085 Da

IUPAC Name

(3R)-3-(acetyloxy)-3-[(1R,2R,5R,6S,7R,10S,11R,14S)-11-(furan-3-yl)-5-(2-hydroxypropan-2-yl)-2,6,10-trimethyl-3,13-dioxo-12,15-dioxatetracyclo[8.5.0.0^{1,14}.0^{2,7}]pentadecan-6-yl]propanoic acid

Traditional Name

(3R)-3-(acetyloxy)-3-[(1R,2R,5R,6S,7R,10S,11R,14S)-11-(furan-3-yl)-5-(2-hydroxypropan-2-yl)-2,6,10-trimethyl-3,13-dioxo-12,15-dioxatetracyclo[8.5.0.0^{1,14}.0^{2,7}]pentadecan-6-yl]propanoic acid

CAS Registry Number

Not Available

SMILES

CC(=O)O[C@H](CC(O)=O)[C@]1(C)[C@@H](CC(=O)[C@]2(C)[C@@H]1CC[C@@]1(C)[C@@H](OC(=O)[C@H]3O[C@@]213)C1=COC=C1)C(C)(C)O

InChI Identifier

InChI=1S/C28H36O10/c1-14(29)36-19(12-20(31)32)26(5)16-7-9-25(4)21(15-8-10-35-13-15)37-23(33)22-28(25,38-22)27(16,6)18(30)11-17(26)24(2,3)34/h8,10,13,16-17,19,21-22,34H,7,9,11-12H2,1-6H3,(H,31,32)/t16-,17+,19-,21+,22-,25+,26+,27+,28-/m1/s1

InChI Key

ZIKZPLSIAVHITA-FNCGWBFLSA-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
Citrus limon	Plant	KNApSAcK
Citrus medica	LOTUS Database	35616633
Citrus paradisi L.	Plant	KNApSAcK
Citrus sudachi	Plant	KNApSAcK
Ciyrus aurantium	-	KNApSAcK
Ciyrus junos	-	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as steroid lactones. These are sterol lipids containing a lactone moiety linked to the steroid skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Steroid lactones

Direct Parent

Steroid lactones

Alternative Parents

Substituents

Steroid lactone
Steroid acid
17-hydroxysteroid
2-oxosteroid
Oxosteroid
11-oxosteroid
Hydroxysteroid
Naphthopyran
Naphthalene
Tricarboxylic acid or derivatives
Carbocyclic fatty acid
Delta_valerolactone
Hydroxy fatty acid
Dioxepane
Delta valerolactone
1,4-dioxepane
Fatty acyl
Pyran
Oxane
Heteroaromatic compound
Tertiary alcohol
Furan
Lactone
Ketone
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Ether
Oxirane
Dialkyl ether
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
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	2.81	ALOGPS
logP	2.35	ChemAxon
logS	-3.9	ALOGPS
pKa (Strongest Acidic)	4.1	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	149.57 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	129.1 m³·mol⁻¹	ChemAxon
Polarizability	54.2 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	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

162978918

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Nomilinic acid (NP0078031)

MOL for NP0078031 (Nomilinic acid)

3D MOL for NP0078031 (Nomilinic acid)

3D SDF for NP0078031 (Nomilinic acid)

3D-SDF for NP0078031 (Nomilinic acid)

PDB for NP0078031 (Nomilinic acid)

3D PDB for NP0078031 (Nomilinic acid)

SMILES for NP0078031 (Nomilinic acid)

INCHI for NP0078031 (Nomilinic acid)

Structure for NP0078031 (Nomilinic acid)

3D Structure for NP0078031 (Nomilinic acid)