NP-MRD: Showing NP-Card for ruageanin b (NP0194444)

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Record Information

Version

2.0

Created at

2022-09-04 12:06:00 UTC

Updated at

2022-09-04 12:06:00 UTC

NP-MRD ID

NP0194444

Secondary Accession Numbers

None

Natural Product Identification

Common Name

ruageanin b

Description

Ruageanin B 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. ruageanin b is found in Heynea trijuga, Swietenia macrophylla and Swietenia mahagoni. Based on a literature review very few articles have been published on ruageanin B.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309042214062D          

 42 47  0  0  1  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652309042214062D          

 42 47  0  0  1  0            999 V2000
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    0.3284    0.9385    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3242    0.2191    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1283    0.3909    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9086   -0.4366    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4765   -1.1954    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8124   -1.9493    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6291   -2.0329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1086   -1.3574    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4519   -2.1075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9299   -1.4356    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2728   -2.1860    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0814   -2.3496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1756   -3.1692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4253   -3.5121    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8673   -2.9044    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4082   -0.7635    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0653   -0.0131    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5437    0.6590    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2441    0.0651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7657   -0.6070    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  8  7  1  6  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
  9 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  1  0  0  0  0
 12 18  1  0  0  0  0
 18 19  1  1  0  0  0
 18 20  1  0  0  0  0
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
  8 22  1  0  0  0  0
 22 23  1  1  0  0  0
 22 24  1  0  0  0  0
 24 25  1  1  0  0  0
 26 25  1  1  0  0  0
 24 26  1  0  0  0  0
 26 27  1  0  0  0  0
 18 27  1  0  0  0  0
 27 28  1  6  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  1  0  0  0
 30 32  1  0  0  0  0
 32 33  1  1  0  0  0
 33 34  1  0  0  0  0
 34 35  2  0  0  0  0
 35 36  1  0  0  0  0
 36 37  1  0  0  0  0
 33 37  2  0  0  0  0
 32 38  1  0  0  0  0
 38 39  1  0  0  0  0
 39 40  2  0  0  0  0
 39 41  1  0  0  0  0
 42 41  1  6  0  0  0
 26 42  1  0  0  0  0
 30 42  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0194444

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)C[C@H]1C(C)(C)[C@H](OC(=O)C(\C)=C\C)[C@]2(O)[C@H]3O[C@@]33[C@H](CC[C@]4(C)[C@H]3CC(=O)O[C@H]4C3=COC=C3)[C@@]1(C)C2=O

> <INCHI_IDENTIFIER>
InChI=1S/C32H40O10/c1-8-16(2)24(35)41-26-28(3,4)19(13-21(33)38-7)30(6)18-9-11-29(5)20(32(18)27(42-32)31(26,37)25(30)36)14-22(34)40-23(29)17-10-12-39-15-17/h8,10,12,15,18-20,23,26-27,37H,9,11,13-14H2,1-7H3/b16-8+/t18-,19+,20-,23+,26+,27-,29-,30-,31+,32-/m1/s1

> <INCHI_KEY>
RHNVFPUACKXTEQ-DEBVYSQHSA-N

> <FORMULA>
C32H40O10

> <MOLECULAR_WEIGHT>
584.662

> <EXACT_MASS>
584.262147488

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
82

> <JCHEM_AVERAGE_POLARIZABILITY>
60.78010041341872

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,2R,4S,5R,9R,10R,13R,14S,15S,17S)-9-(furan-3-yl)-1-hydroxy-15-(2-methoxy-2-oxoethyl)-10,14,16,16-tetramethyl-7,18-dioxo-3,8-dioxapentacyclo[12.3.1.0^{2,4}.0^{4,13}.0^{5,10}]octadecan-17-yl (2E)-2-methylbut-2-enoate

> <JCHEM_LOGP>
4.191301287666668

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.110785855757564

> <JCHEM_PKA_STRONGEST_BASIC>
-2.87047453073211

> <JCHEM_POLAR_SURFACE_AREA>
141.87

> <JCHEM_REFRACTIVITY>
146.38119999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2R,4S,5R,9R,10R,13R,14S,15S,17S)-9-(furan-3-yl)-1-hydroxy-15-(2-methoxy-2-oxoethyl)-10,14,16,16-tetramethyl-7,18-dioxo-3,8-dioxapentacyclo[12.3.1.0^{2,4}.0^{4,13}.0^{5,10}]octadecan-17-yl (2E)-2-methylbut-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-22         0                                  
HETATM    1  C   UNK     0      -4.518   4.857   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -3.585   3.632   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -4.180   2.211   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -5.708   2.016   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -3.247   0.986   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      -3.842  -0.435   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0      -1.720   1.181   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -0.787  -0.045   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.467  -1.503   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -2.754  -0.656   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -2.491  -2.653   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.441  -2.725   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.993  -4.163   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.025  -5.360   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       1.497  -5.119   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0      -0.577  -6.797   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       0.392  -7.994   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.163  -2.501   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.397  -4.023   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.009  -1.128   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       2.538  -0.939   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       0.826   0.227   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       0.613   1.752   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       2.472   0.409   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       3.973   0.730   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       3.563  -0.815   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       2.756  -2.232   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       3.383  -3.639   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       4.908  -3.795   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       5.803  -2.534   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       6.444  -3.934   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       7.336  -2.680   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       7.976  -4.080   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       9.485  -4.386   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       9.661  -5.916   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0       8.260  -6.556   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0       7.219  -5.422   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0       8.229  -1.425   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0       7.589  -0.024   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0       8.482   1.230   0.000  0.00  0.00           O+0
HETATM   41  C   UNK     0       6.056   0.122   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0       5.163  -1.133   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9   22                                                  
CONECT    9    8   10   11   12                                             
CONECT   10    9                                                            
CONECT   11    9                                                            
CONECT   12    9   13   18                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17                                                       
CONECT   17   16                                                            
CONECT   18   12   19   20   27                                             
CONECT   19   18                                                            
CONECT   20   18   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20    8   23   24                                             
CONECT   23   22                                                            
CONECT   24   22   25   26                                                  
CONECT   25   24   26                                                       
CONECT   26   25   24   27   42                                             
CONECT   27   26   18   28                                                  
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   31   32   42                                             
CONECT   31   30                                                            
CONECT   32   30   33   38                                                  
CONECT   33   32   34   37                                                  
CONECT   34   33   35                                                       
CONECT   35   34   36                                                       
CONECT   36   35   37                                                       
CONECT   37   36   33                                                       
CONECT   38   32   39                                                       
CONECT   39   38   40   41                                                  
CONECT   40   39                                                            
CONECT   41   39   42                                                       
CONECT   42   41   26   30                                                  
MASTER        0    0    0    0    0    0    0    0   42    0   94    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₂H₄₀O₁₀

Average Mass

584.6620 Da

Monoisotopic Mass

584.26215 Da

IUPAC Name

(1S,2R,4S,5R,9R,10R,13R,14S,15S,17S)-9-(furan-3-yl)-1-hydroxy-15-(2-methoxy-2-oxoethyl)-10,14,16,16-tetramethyl-7,18-dioxo-3,8-dioxapentacyclo[12.3.1.0^{2,4}.0^{4,13}.0^{5,10}]octadecan-17-yl (2E)-2-methylbut-2-enoate

Traditional Name

CAS Registry Number

Not Available

SMILES

COC(=O)C[C@H]1C(C)(C)[C@H](OC(=O)C(\C)=C\C)[C@]2(O)[C@H]3O[C@@]33[C@H](CC[C@]4(C)[C@H]3CC(=O)O[C@H]4C3=COC=C3)[C@@]1(C)C2=O

InChI Identifier

InChI=1S/C32H40O10/c1-8-16(2)24(35)41-26-28(3,4)19(13-21(33)38-7)30(6)18-9-11-29(5)20(32(18)27(42-32)31(26,37)25(30)36)14-22(34)40-23(29)17-10-12-39-15-17/h8,10,12,15,18-20,23,26-27,37H,9,11,13-14H2,1-7H3/b16-8+/t18-,19+,20-,23+,26+,27-,29-,30-,31+,32-/m1/s1

InChI Key

RHNVFPUACKXTEQ-DEBVYSQHSA-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
Heynea trijuga	LOTUS Database	35616633
Swietenia macrophylla	LOTUS Database	35616633
Swietenia mahagoni	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
Mexicanolide
Naphthopyran
Naphthalene
Tricarboxylic acid or derivatives
Delta valerolactone
Fatty acid ester
Delta_valerolactone
Oxepane
Fatty acyl
Oxane
Pyran
Cyclic alcohol
Furan
Heteroaromatic compound
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Methyl ester
Tertiary alcohol
Lactone
Ketone
Carboxylic acid ester
Ether
Oxirane
Dialkyl ether
Oxacycle
Organoheterocyclic compound
Carboxylic acid derivative
Carbonyl group
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Alcohol
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

limonoid (CHEBI:68371 )

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	4.19	ChemAxon
pKa (Strongest Acidic)	11.11	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	141.87 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	146.38 m³·mol⁻¹	ChemAxon
Polarizability	60.78 Å³	ChemAxon
Number of Rings	6	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

9976101

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11801433

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for ruageanin b (NP0194444)

MOL for NP0194444 (ruageanin b)

3D MOL for NP0194444 (ruageanin b)

3D SDF for NP0194444 (ruageanin b)

3D-SDF for NP0194444 (ruageanin b)

PDB for NP0194444 (ruageanin b)

3D PDB for NP0194444 (ruageanin b)

SMILES for NP0194444 (ruageanin b)

INCHI for NP0194444 (ruageanin b)

Structure for NP0194444 (ruageanin b)

3D Structure for NP0194444 (ruageanin b)