NP-MRD: Showing NP-Card for Remisporine B (NP0139264)

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Record Information

Version

2.0

Created at

2022-06-29 19:46:37 UTC

Updated at

2022-06-29 19:46:37 UTC

NP-MRD ID

NP0139264

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Remisporine B

Description

Remisporine B belongs to the class of organic compounds known as xanthones. These are polycyclic aromatic compounds containing a xanthene moiety conjugated to a ketone group at carbon 9. Xanthene is a tricyclic compound made up of two benzene rings linearly fused to each other through a pyran ring. Remisporine B was first documented in 2012 (PMID: 23135875). Based on a literature review a small amount of articles have been published on Remisporine B (PMID: 26295241) (PMID: 25735997).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652306292221462D          

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M  END

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  2  7  1  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
  5 11  1  0  0  0  0
 11 12  2  0  0  0  0
 10 13  1  0  0  0  0
 14 13  1  1  0  0  0
 14 15  1  0  0  0  0
 15 16  1  6  0  0  0
  9 16  1  0  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 14 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 13 21  1  1  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 23 28  1  0  0  0  0
 28 29  1  0  0  0  0
 20 29  1  0  0  0  0
 29 30  2  0  0  0  0
 27 31  1  0  0  0  0
 25 32  1  0  0  0  0
 19 33  1  6  0  0  0
 33 34  2  0  0  0  0
 33 35  1  0  0  0  0
 35 36  1  0  0  0  0
 17 37  1  6  0  0  0
 37 38  2  0  0  0  0
 37 39  1  0  0  0  0
 39 40  1  0  0  0  0
 17 41  1  1  0  0  0
  4 42  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0139264

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)[C@]1(O)O[C@@]2([C@@H]3[C@@H]1CC1=C([C@@H]3C3=C2C(=O)C2=C(O)C=C(C)C=C2O3)C(=O)C2=C(O)C=C(C)C=C2O1)C(=O)OC

> <INCHI_IDENTIFIER>
InChI=1S/C30H24O12/c1-10-5-13(31)18-15(7-10)40-17-9-12-22-21(20(17)24(18)33)26-23(25(34)19-14(32)6-11(2)8-16(19)41-26)29(22,27(35)38-3)42-30(12,37)28(36)39-4/h5-8,12,21-22,31-32,37H,9H2,1-4H3/t12-,21-,22+,29+,30+/m0/s1

> <INCHI_KEY>
RRGJMIUFDPLICY-FHJGPULQSA-N

> <FORMULA>
C30H24O12

> <MOLECULAR_WEIGHT>
576.51

> <EXACT_MASS>
576.126776213

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
66

> <JCHEM_AVERAGE_POLARIZABILITY>
57.67017247887432

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
12,14-dimethyl (1R,12R,14R,15S,27S)-8,14,23-trihydroxy-6,21-dimethyl-10,25-dioxo-3,13,18-trioxaheptacyclo[13.11.1.0^{2,11}.0^{4,9}.0^{12,27}.0^{17,26}.0^{19,24}]heptacosa-2(11),4,6,8,17(26),19,21,23-octaene-12,14-dicarboxylate

> <ALOGPS_LOGP>
2.76

> <JCHEM_LOGP>
3.699225715666668

> <ALOGPS_LOGS>
-3.65

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
7.269195524524726

> <JCHEM_PKA_STRONGEST_ACIDIC>
-10.928630609540107

> <JCHEM_PKA_STRONGEST_BASIC>
0.6463535989377345

> <JCHEM_POLAR_SURFACE_AREA>
175.11999999999998

> <JCHEM_REFRACTIVITY>
143.2502

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.30e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
12,14-dimethyl (1R,12R,14R,15S,27S)-8,14,23-trihydroxy-6,21-dimethyl-10,25-dioxo-3,13,18-trioxaheptacyclo[13.11.1.0^{2,11}.0^{4,9}.0^{12,27}.0^{17,26}.0^{19,24}]heptacosa-2(11),4,6,8,17(26),19,21,23-octaene-12,14-dicarboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 29-JUN-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-JUN-22         0                                  
HETATM    1  C   UNK     0      21.894  -0.030   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      20.370  -0.253   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      19.415   0.955   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      17.891   0.732   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      17.322  -0.699   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      18.278  -1.907   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      19.801  -1.684   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      17.709  -3.338   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      16.185  -3.561   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      15.230  -2.353   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      15.799  -0.922   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      14.844   0.286   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      13.706  -2.577   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      13.138  -4.008   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      14.093  -5.216   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      15.617  -4.993   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      13.239  -6.497   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      11.756  -6.082   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      11.694  -4.543   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      10.739  -3.335   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      11.592  -2.053   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      10.909  -0.673   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       9.372  -0.574   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       8.689   0.806   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       7.152   0.904   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       6.299  -0.377   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       6.982  -1.758   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       8.519  -1.856   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       9.202  -3.236   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       8.348  -4.518   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0       6.128  -3.039   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       6.469   2.285   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      10.250  -5.078   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       9.064  -4.095   0.000  0.00  0.00           O+0
HETATM   35  O   UNK     0       9.991  -6.596   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0       8.547  -7.131   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      12.996  -8.018   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0      14.192  -8.989   0.000  0.00  0.00           O+0
HETATM   39  O   UNK     0      11.558  -8.568   0.000  0.00  0.00           O+0
HETATM   40  C   UNK     0      11.315 -10.089   0.000  0.00  0.00           C+0
HETATM   41  O   UNK     0      14.414  -7.493   0.000  0.00  0.00           O+0
HETATM   42  O   UNK     0      16.936   1.940   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    7                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   42                                                  
CONECT    5    4    6   11                                                  
CONECT    6    5    7    8                                                  
CONECT    7    6    2                                                       
CONECT    8    6    9                                                       
CONECT    9    8   10   16                                                  
CONECT   10    9   11   13                                                  
CONECT   11   10    5   12                                                  
CONECT   12   11                                                            
CONECT   13   10   14   21                                                  
CONECT   14   13   15   19                                                  
CONECT   15   14   16   17                                                  
CONECT   16   15    9                                                       
CONECT   17   15   18   37   41                                             
CONECT   18   17   19                                                       
CONECT   19   18   14   20   33                                             
CONECT   20   19   21   29                                                  
CONECT   21   20   13   22                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24   28                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26   32                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28   31                                                  
CONECT   28   27   23   29                                                  
CONECT   29   28   20   30                                                  
CONECT   30   29                                                            
CONECT   31   27                                                            
CONECT   32   25                                                            
CONECT   33   19   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33   36                                                       
CONECT   36   35                                                            
CONECT   37   17   38   39                                                  
CONECT   38   37                                                            
CONECT   39   37   40                                                       
CONECT   40   39                                                            
CONECT   41   17                                                            
CONECT   42    4                                                            
MASTER        0    0    0    0    0    0    0    0   42    0   96    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₀H₂₄O₁₂

Average Mass

576.5100 Da

Monoisotopic Mass

576.12678 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

COC(=O)[C@]1(O)O[C@@]2([C@@H]3[C@@H]1CC1=C([C@@H]3C3=C2C(=O)C2=C(O)C=C(C)C=C2O3)C(=O)C2=C(O)C=C(C)C=C2O1)C(=O)OC

InChI Identifier

InChI=1S/C30H24O12/c1-10-5-13(31)18-15(7-10)40-17-9-12-22-21(20(17)24(18)33)26-23(25(34)19-14(32)6-11(2)8-16(19)41-26)29(22,27(35)38-3)42-30(12,37)28(36)39-4/h5-8,12,21-22,31-32,37H,9H2,1-4H3/t12-,21-,22+,29+,30+/m0/s1

InChI Key

RRGJMIUFDPLICY-FHJGPULQSA-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

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as xanthones. These are polycyclic aromatic compounds containing a xanthene moiety conjugated to a ketone group at carbon 9. Xanthene is a tricyclic compound made up of two benzene rings linearly fused to each other through a pyran ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzopyrans

Sub Class

1-benzopyrans

Direct Parent

Xanthones

Alternative Parents

Substituents

Xanthone
Chromone
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Pyranone
Dicarboxylic acid or derivatives
Pyran
Benzenoid
Oxolane
Heteroaromatic compound
Vinylogous acid
Methyl ester
Hemiacetal
Carboxylic acid ester
Polyol
Oxacycle
Carboxylic acid derivative
Hydrocarbon derivative
Organooxygen compound
Organic oxide
Organic oxygen 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

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

8523601

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10348143

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Xia MW, Cui CB, Li CW, Wu CJ, Peng JX, Li DH: Rare Chromones from a Fungal Mutant of the Marine-Derived Penicillium purpurogenum G59. Mar Drugs. 2015 Aug 18;13(8):5219-36. doi: 10.3390/md13085219. [PubMed:26295241 ]
Sherer EC, Cheeseman JR, Williamson RT: Absolute configuration of remisporines A & B. Org Biomol Chem. 2015 Apr 14;13(14):4169-73. doi: 10.1039/c5ob00082c. Epub 2015 Mar 4. [PubMed:25735997 ]
Kong F, Zhu T, Pan W, Tsao R, Pagano TG, Nguyen B, Marquez B: WYE-120318, a ring contraction product of methylnaltrexone, and structure revision of coniothyrione. Magn Reson Chem. 2012 Dec;50(12):829-33. doi: 10.1002/mrc.3892. Epub 2012 Nov 8. [PubMed:23135875 ]

Showing NP-Card for Remisporine B (NP0139264)

MOL for NP0139264 (Remisporine B)

3D MOL for NP0139264 (Remisporine B)

3D SDF for NP0139264 (Remisporine B)

3D-SDF for NP0139264 (Remisporine B)

PDB for NP0139264 (Remisporine B)

3D PDB for NP0139264 (Remisporine B)

SMILES for NP0139264 (Remisporine B)

INCHI for NP0139264 (Remisporine B)

Structure for NP0139264 (Remisporine B)

3D Structure for NP0139264 (Remisporine B)