NP-MRD: Showing NP-Card for (+)-Cineracipadesin B (NP0081407)

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Record Information

Version

2.0

Created at

2022-04-29 02:22:56 UTC

Updated at

2022-04-29 02:22:56 UTC

NP-MRD ID

NP0081407

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(+)-Cineracipadesin B

Description

Cineracipadesin B belongs to the class of organic compounds known as tetracarboxylic acids and derivatives. These are carboxylic acids containing exactly four carboxyl groups. (+)-Cineracipadesin B is found in Cipadessa cinerascens. Based on a literature review very few articles have been published on cineracipadesin B.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304292204222D          

 43 47  0  0  1  0            999 V2000
    4.0877    1.7495    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.2539    0.9414    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.6057    0.3430    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.0102   -0.2744    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
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 39 41  1  0  0  0  0
 41 42  1  0  0  0  0
  2 43  1  6  0  0  0
M  END

     RDKit          3D

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M  END


  Mrv1652304292204222D          

 43 47  0  0  1  0            999 V2000
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    5.0368    0.6813    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.6535    1.2292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4874    2.0373    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.7044    2.2974    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.5383    3.1055    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7553    3.3657    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1386    2.8177    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5892    4.1737    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1041    2.5853    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9379    3.3934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1550    3.6535    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5546    3.9413    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2227    0.6320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4669    1.3671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2030   -0.1268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9859   -0.3869    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6026    0.1610    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1521   -1.1950    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9350   -1.4552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4278    0.1349    0.0000 C   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
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  1  8  1  1  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
  6 13  1  0  0  0  0
 13 14  1  6  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 14 18  2  0  0  0  0
  7 19  1  6  0  0  0
  3 19  1  0  0  0  0
 19 20  2  0  0  0  0
  6 21  1  6  0  0  0
  4 22  1  6  0  0  0
  3 23  1  6  0  0  0
  2 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
  1 27  1  0  0  0  0
 27 28  1  1  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 29 31  1  0  0  0  0
 26 32  1  1  0  0  0
 32 33  1  0  0  0  0
 33 34  2  0  0  0  0
 33 35  1  0  0  0  0
 25 36  1  0  0  0  0
 25 37  1  0  0  0  0
 24 38  1  6  0  0  0
 38 39  1  0  0  0  0
 39 40  2  0  0  0  0
 39 41  1  0  0  0  0
 41 42  1  0  0  0  0
  2 43  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0081407

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)C[C@H]1C(C)(C)[C@H](OC(C)=O)[C@H](OC(C)=O)[C@@H]2O[C@]34CC(=O)O[C@@H](C5=COC=C5)[C@]3(C)C[C@@H](O)[C@@](O)(C4=C)[C@]12C

> <INCHI_IDENTIFIER>
InChI=1S/C31H40O12/c1-15-30-13-22(36)42-24(18-9-10-39-14-18)28(30,6)12-20(34)31(15,37)29(7)19(11-21(35)38-8)27(4,5)25(41-17(3)33)23(26(29)43-30)40-16(2)32/h9-10,14,19-20,23-26,34,37H,1,11-13H2,2-8H3/t19-,20+,23-,24-,25+,26-,28-,29+,30-,31-/m0/s1

> <INCHI_KEY>
FHDMRXVKCNUYLT-PSNIBAITSA-N

> <FORMULA>
C31H40O12

> <MOLECULAR_WEIGHT>
604.649

> <EXACT_MASS>
604.251976728

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
83

> <JCHEM_AVERAGE_POLARIZABILITY>
60.35981734524097

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
methyl 2-[(1R,3R,4R,5S,7S,8R,9S,10R,12S,13R)-4,5-bis(acetyloxy)-13-(furan-3-yl)-9,10-dihydroxy-6,6,8,12-tetramethyl-17-methylidene-15-oxo-2,14-dioxatetracyclo[7.7.1.0^{1,12}.0^{3,8}]heptadecan-7-yl]acetate

> <ALOGPS_LOGP>
2.44

> <JCHEM_LOGP>
1.1397863173333342

> <ALOGPS_LOGS>
-3.78

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.706348571336257

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.78789991525354

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8702508646169775

> <JCHEM_POLAR_SURFACE_AREA>
168.03

> <JCHEM_REFRACTIVITY>
144.4645

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.01e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl [(1R,3R,4R,5S,7S,8R,9S,10R,12S,13R)-4,5-bis(acetyloxy)-13-(furan-3-yl)-9,10-dihydroxy-6,6,8,12-tetramethyl-17-methylidene-15-oxo-2,14-dioxatetracyclo[7.7.1.0^{1,12}.0^{3,8}]heptadecan-7-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       7.630   3.266   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       7.941   1.757   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.731   0.640   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.619  -0.512   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.057  -0.186   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.664   1.377   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.755   2.643   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       6.075   3.702   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       3.942   4.018   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.389   4.186   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       1.764   5.594   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       1.478   2.931   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       2.094   1.526   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.192   0.278   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.671  -1.186   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.427  -2.094   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -0.821  -1.191   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      -0.348   0.275   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.730   1.645   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.634   0.564   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.661   0.209   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       6.072  -1.984   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       7.808  -0.460   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       9.402   1.272   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      10.553   2.295   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      10.243   3.803   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       8.782   4.289   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       8.471   5.797   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       7.010   6.283   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       5.859   5.260   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       6.700   7.791   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      11.394   4.826   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0      11.084   6.334   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       9.623   6.820   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0      12.235   7.357   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      11.616   1.180   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      12.072   2.552   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       9.712  -0.237   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      11.174  -0.722   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0      12.325   0.301   0.000  0.00  0.00           O+0
HETATM   41  O   UNK     0      11.484  -2.231   0.000  0.00  0.00           O+0
HETATM   42  C   UNK     0      12.945  -2.716   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0       8.265   0.252   0.000  0.00  0.00           C+0
CONECT    1    2    8   27                                                  
CONECT    2    1    3   24   43                                             
CONECT    3    2    4   19   23                                             
CONECT    4    3    5   22                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7   13   21                                             
CONECT    7    6    8    9   19                                             
CONECT    8    7    1                                                       
CONECT    9    7   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12    6   14                                                  
CONECT   14   13   15   18                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   14                                                       
CONECT   19    7    3   20                                                  
CONECT   20   19                                                            
CONECT   21    6                                                            
CONECT   22    4                                                            
CONECT   23    3                                                            
CONECT   24    2   25   38                                                  
CONECT   25   24   26   36   37                                             
CONECT   26   25   27   32                                                  
CONECT   27   26    1   28                                                  
CONECT   28   27   29                                                       
CONECT   29   28   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29                                                            
CONECT   32   26   33                                                       
CONECT   33   32   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33                                                            
CONECT   36   25                                                            
CONECT   37   25                                                            
CONECT   38   24   39                                                       
CONECT   39   38   40   41                                                  
CONECT   40   39                                                            
CONECT   41   39   42                                                       
CONECT   42   41                                                            
CONECT   43    2                                                            
MASTER        0    0    0    0    0    0    0    0   43    0   94    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₁H₄₀O₁₂

Average Mass

604.6490 Da

Monoisotopic Mass

604.25198 Da

IUPAC Name

methyl 2-[(1R,3R,4R,5S,7S,8R,9S,10R,12S,13R)-4,5-bis(acetyloxy)-13-(furan-3-yl)-9,10-dihydroxy-6,6,8,12-tetramethyl-17-methylidene-15-oxo-2,14-dioxatetracyclo[7.7.1.0^{1,12}.0^{3,8}]heptadecan-7-yl]acetate

Traditional Name

methyl [(1R,3R,4R,5S,7S,8R,9S,10R,12S,13R)-4,5-bis(acetyloxy)-13-(furan-3-yl)-9,10-dihydroxy-6,6,8,12-tetramethyl-17-methylidene-15-oxo-2,14-dioxatetracyclo[7.7.1.0^{1,12}.0^{3,8}]heptadecan-7-yl]acetate

CAS Registry Number

Not Available

SMILES

COC(=O)C[C@H]1C(C)(C)[C@H](OC(C)=O)[C@H](OC(C)=O)[C@@H]2O[C@]34CC(=O)O[C@@H](C5=COC=C5)[C@]3(C)C[C@@H](O)[C@@](O)(C4=C)[C@]12C

InChI Identifier

InChI=1S/C31H40O12/c1-15-30-13-22(36)42-24(18-9-10-39-14-18)28(30,6)12-20(34)31(15,37)29(7)19(11-21(35)38-8)27(4,5)25(41-17(3)33)23(26(29)43-30)40-16(2)32/h9-10,14,19-20,23-26,34,37H,1,11-13H2,2-8H3/t19-,20+,23-,24-,25+,26-,28-,29+,30-,31-/m0/s1

InChI Key

FHDMRXVKCNUYLT-PSNIBAITSA-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
Cipadessa cinerascens	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as tetracarboxylic acids and derivatives. These are carboxylic acids containing exactly four carboxyl groups.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Tetracarboxylic acids and derivatives

Direct Parent

Tetracarboxylic acids and derivatives

Alternative Parents

Substituents

Tetracarboxylic acid or derivatives
Delta valerolactone
Delta_valerolactone
Oxane
Cyclic alcohol
Heteroaromatic compound
Furan
Methyl ester
Tertiary alcohol
1,2-diol
Carboxylic acid ester
Secondary alcohol
Lactone
Oxacycle
Dialkyl ether
Ether
Organoheterocyclic compound
Organic oxygen compound
Hydrocarbon derivative
Organic oxide
Alcohol
Carbonyl group
Organooxygen compound
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	2.44	ALOGPS
logP	1.14	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Acidic)	12.79	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	168.03 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	144.46 m³·mol⁻¹	ChemAxon
Polarizability	60.36 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

C00047419

Chemspider ID

24611050

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

42639673

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for (+)-Cineracipadesin B (NP0081407)

MOL for NP0081407 ((+)-Cineracipadesin B)

3D MOL for NP0081407 ((+)-Cineracipadesin B)

3D SDF for NP0081407 ((+)-Cineracipadesin B)

3D-SDF for NP0081407 ((+)-Cineracipadesin B)

PDB for NP0081407 ((+)-Cineracipadesin B)

3D PDB for NP0081407 ((+)-Cineracipadesin B)

SMILES for NP0081407 ((+)-Cineracipadesin B)

INCHI for NP0081407 ((+)-Cineracipadesin B)

Structure for NP0081407 ((+)-Cineracipadesin B)

3D Structure for NP0081407 ((+)-Cineracipadesin B)