NP-MRD: Showing NP-Card for Rubriflorin C (NP0077083)

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Record Information

Version

2.0

Created at

2022-04-28 22:15:05 UTC

Updated at

2022-04-28 22:15:05 UTC

NP-MRD ID

NP0077083

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Rubriflorin C

Description

Ethyl 2-[(1S,3R,4S,7R,8S,9S,11S,14S,17S,26S)-4,9,11,19,19-pentamethyl-5,10,24-trioxo-2,6,18,25-tetraoxaheptacyclo[12.10.1.1¹,⁸.0³,⁷.0¹⁴,²³.0¹⁶,²⁰.0¹¹,²⁶]Hexacosa-16(20),22-dien-17-yl]acetate belongs to the class of organic compounds known as furopyrans. These are organic polycyclic compounds containing a furan ring fused to a pyran ring. Furan is a five-membered aromatic ring with four carbon atoms and one oxygen atom. Pyran a six-membered heterocyclic, non-aromatic ring, made up of five carbon atoms and one oxygen atom and containing two double bonds. Rubriflorin C is found in Schisandra rubriflora. Based on a literature review very few articles have been published on ethyl 2-[(1S,3R,4S,7R,8S,9S,11S,14S,17S,26S)-4,9,11,19,19-pentamethyl-5,10,24-trioxo-2,6,18,25-tetraoxaheptacyclo[12.10.1.1¹,⁸.0³,⁷.0¹⁴,²³.0¹⁶,²⁰.0¹¹,²⁶]Hexacosa-16(20),22-dien-17-yl]acetate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304292200152D          

 40 46  0  0  1  0            999 V2000
    7.1607    1.9573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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 39 40  1  0  0  0  0
M  END

     RDKit          3D

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M  END


  Mrv1652304292200152D          

 40 46  0  0  1  0            999 V2000
    7.1607    1.9573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7409    2.5659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.6557    2.0479    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.6085    2.8715    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5474    1.1176    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2761   -1.0787    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5749    0.6474    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.2040    1.1812    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.8907    1.9444    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6129    2.3433    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9236    2.7688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6369   -0.1752    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9555   -0.6403    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2121   -0.2827    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.0176   -1.4630    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.3362   -1.9280    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3982   -2.7507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  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
  1  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 11 10  1  6  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
  1 13  1  0  0  0  0
 13 14  2  0  0  0  0
 12 15  1  0  0  0  0
 16 15  1  1  0  0  0
 16 17  1  0  0  0  0
 18 17  1  6  0  0  0
 11 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 10 20  1  0  0  0  0
 20 21  2  0  0  0  0
 19 22  1  1  0  0  0
 17 23  1  1  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 24 26  1  0  0  0  0
 16 26  1  0  0  0  0
 26 27  1  1  0  0  0
 12 28  1  6  0  0  0
  7 28  1  6  0  0  0
 10 29  1  1  0  0  0
  5 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
  4 32  1  0  0  0  0
 32 33  1  0  0  0  0
 32 34  1  0  0  0  0
 30 35  1  1  0  0  0
 35 36  1  0  0  0  0
 36 37  2  0  0  0  0
 36 38  1  0  0  0  0
 38 39  1  0  0  0  0
 39 40  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0077083

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCOC(=O)C[C@@H]1OC(C)(C)C2=C1C[C@]13CC[C@@]4(C)[C@@H]5[C@H]([C@H](C)C4=O)[C@H]4OC(=O)[C@@H](C)[C@H]4O[C@@]5(O1)C(=O)C3=CC2

> <INCHI_IDENTIFIER>
InChI=1S/C31H38O9/c1-7-36-20(32)12-19-16-13-30-11-10-29(6)24-21(14(2)25(29)33)23-22(15(3)27(35)37-23)39-31(24,40-30)26(34)18(30)9-8-17(16)28(4,5)38-19/h9,14-15,19,21-24H,7-8,10-13H2,1-6H3/t14-,15-,19-,21+,22+,23+,24-,29-,30-,31-/m0/s1

> <INCHI_KEY>
RBSLMMGBSAUALR-JBZSFQMUSA-N

> <FORMULA>
C31H38O9

> <MOLECULAR_WEIGHT>
554.636

> <EXACT_MASS>
554.251582804

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
78

> <JCHEM_AVERAGE_POLARIZABILITY>
59.09374527571905

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
ethyl 2-[(1S,3R,4S,7R,8S,9S,11S,14S,17S,26S)-4,9,11,19,19-pentamethyl-5,10,24-trioxo-2,6,18,25-tetraoxaheptacyclo[12.10.1.1^{1,8}.0^{3,7}.0^{14,23}.0^{16,20}.0^{11,26}]hexacosa-16(20),22-dien-17-yl]acetate

> <ALOGPS_LOGP>
3.48

> <JCHEM_LOGP>
3.8572441356666647

> <ALOGPS_LOGS>
-4.35

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
18.272489892509387

> <JCHEM_PKA_STRONGEST_BASIC>
-3.890783744541753

> <JCHEM_POLAR_SURFACE_AREA>
114.43000000000002

> <JCHEM_REFRACTIVITY>
141.25680000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.47e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
ethyl [(1S,3R,4S,7R,8S,9S,11S,14S,17S,26S)-4,9,11,19,19-pentamethyl-5,10,24-trioxo-2,6,18,25-tetraoxaheptacyclo[12.10.1.1^{1,8}.0^{3,7}.0^{14,23}.0^{16,20}.0^{11,26}]hexacosa-16(20),22-dien-17-yl]acetate

> <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      13.367   3.654   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      14.450   4.790   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      16.002   4.750   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      16.927   3.514   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      16.563   2.017   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      15.139   1.437   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      13.660   2.055   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      13.768   0.424   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      12.735  -0.757   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      11.154  -0.579   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      10.347   0.807   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      10.862   2.389   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      11.717   3.824   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      11.026   5.200   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0       9.614   3.403   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       8.120   2.990   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       7.728   1.501   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.831   0.394   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       8.700  -1.177   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      10.131  -1.763   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      10.488  -3.261   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       7.387  -1.981   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       6.191   1.413   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       5.632   2.848   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       4.142   3.239   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       6.824   3.823   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       6.736   5.360   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      12.222   2.086   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      11.715  -2.013   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      17.873   1.209   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      19.047   2.205   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      18.463   3.630   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      19.811   4.374   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      18.524   5.168   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      17.989  -0.327   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      16.717  -1.195   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0      15.329  -0.528   0.000  0.00  0.00           O+0
HETATM   38  O   UNK     0      16.833  -2.731   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0      15.561  -3.599   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      15.677  -5.135   0.000  0.00  0.00           C+0
CONECT    1    2    7   13                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5   32                                                  
CONECT    5    4    6   30                                                  
CONECT    6    5    7                                                       
CONECT    7    6    1    8   28                                             
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   20   29                                             
CONECT   11   10   12   18                                                  
CONECT   12   11   13   15   28                                             
CONECT   13   12    1   14                                                  
CONECT   14   13                                                            
CONECT   15   12   16                                                       
CONECT   16   15   17   26                                                  
CONECT   17   16   18   23                                                  
CONECT   18   17   11   19                                                  
CONECT   19   18   20   22                                                  
CONECT   20   19   10   21                                                  
CONECT   21   20                                                            
CONECT   22   19                                                            
CONECT   23   17   24                                                       
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   16   27                                                  
CONECT   27   26                                                            
CONECT   28   12    7                                                       
CONECT   29   10                                                            
CONECT   30    5   31   35                                                  
CONECT   31   30   32                                                       
CONECT   32   31    4   33   34                                             
CONECT   33   32                                                            
CONECT   34   32                                                            
CONECT   35   30   36                                                       
CONECT   36   35   37   38                                                  
CONECT   37   36                                                            
CONECT   38   36   39                                                       
CONECT   39   38   40                                                       
CONECT   40   39                                                            
MASTER        0    0    0    0    0    0    0    0   40    0   92    0
END

View in JSmol

Synonyms

Value	Source
Ethyl 2-[(1S,3R,4S,7R,8S,9S,11S,14S,17S,26S)-4,9,11,19,19-pentamethyl-5,10,24-trioxo-2,6,18,25-tetraoxaheptacyclo[12.10.1.1,.0,.0,.0,.0,]hexacosa-16(20),22-dien-17-yl]acetic acid	Generator

Chemical Formula

C₃₁H₃₈O₉

Average Mass

554.6360 Da

Monoisotopic Mass

554.25158 Da

IUPAC Name

ethyl 2-[(1S,3R,4S,7R,8S,9S,11S,14S,17S,26S)-4,9,11,19,19-pentamethyl-5,10,24-trioxo-2,6,18,25-tetraoxaheptacyclo[12.10.1.1^{1,8}.0^{3,7}.0^{14,23}.0^{16,20}.0^{11,26}]hexacosa-16(20),22-dien-17-yl]acetate

Traditional Name

ethyl [(1S,3R,4S,7R,8S,9S,11S,14S,17S,26S)-4,9,11,19,19-pentamethyl-5,10,24-trioxo-2,6,18,25-tetraoxaheptacyclo[12.10.1.1^{1,8}.0^{3,7}.0^{14,23}.0^{16,20}.0^{11,26}]hexacosa-16(20),22-dien-17-yl]acetate

CAS Registry Number

Not Available

SMILES

CCOC(=O)C[C@@H]1OC(C)(C)C2=C1C[C@]13CC[C@@]4(C)[C@@H]5[C@H]([C@H](C)C4=O)[C@H]4OC(=O)[C@@H](C)[C@H]4O[C@@]5(O1)C(=O)C3=CC2

InChI Identifier

InChI=1S/C31H38O9/c1-7-36-20(32)12-19-16-13-30-11-10-29(6)24-21(14(2)25(29)33)23-22(15(3)27(35)37-23)39-31(24,40-30)26(34)18(30)9-8-17(16)28(4,5)38-19/h9,14-15,19,21-24H,7-8,10-13H2,1-6H3/t14-,15-,19-,21+,22+,23+,24-,29-,30-,31-/m0/s1

InChI Key

RBSLMMGBSAUALR-JBZSFQMUSA-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
Schisandra rubriflora	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as furopyrans. These are organic polycyclic compounds containing a furan ring fused to a pyran ring. Furan is a five-membered aromatic ring with four carbon atoms and one oxygen atom. Pyran a six-membered heterocyclic, non-aromatic ring, made up of five carbon atoms and one oxygen atom and containing two double bonds.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Furopyrans

Sub Class

Not Available

Direct Parent

Furopyrans

Alternative Parents

Substituents

Furopyran
Ketal
Oxepane
Pyran
Oxane
Gamma butyrolactone
3-furanone
Dicarboxylic acid or derivatives
Tetrahydrofuran
Furan
Dihydrofuran
Lactone
Ketone
Carboxylic acid ester
Oxacycle
Ether
Dialkyl ether
Carboxylic acid derivative
Acetal
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
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	3.48	ALOGPS
logP	3.86	ChemAxon
logS	-4.4	ALOGPS
pKa (Strongest Acidic)	18.27	ChemAxon
pKa (Strongest Basic)	-3.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	114.43 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	141.26 m³·mol⁻¹	ChemAxon
Polarizability	59.09 Å³	ChemAxon
Number of Rings	7	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	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

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

163105784

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Rubriflorin C (NP0077083)

MOL for NP0077083 (Rubriflorin C)

3D MOL for NP0077083 (Rubriflorin C)

3D SDF for NP0077083 (Rubriflorin C)

3D-SDF for NP0077083 (Rubriflorin C)

PDB for NP0077083 (Rubriflorin C)

3D PDB for NP0077083 (Rubriflorin C)

SMILES for NP0077083 (Rubriflorin C)

INCHI for NP0077083 (Rubriflorin C)

Structure for NP0077083 (Rubriflorin C)

3D Structure for NP0077083 (Rubriflorin C)