NP-MRD: Showing NP-Card for (+)-Murramarin A (NP0072248)

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Record Information

Version

2.0

Created at

2022-04-28 17:36:43 UTC

Updated at

2022-04-28 17:36:43 UTC

NP-MRD ID

NP0072248

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(+)-Murramarin A

Description

(1R)-1-[(2S,5'S)-7-methoxy-5'-[(7-methoxy-2-oxo-2H-chromen-8-yl)methyl]-4',4'-dimethylspiro[chromene-2,2'-[1,3]dioxolane]-8-yl]-3-methyl-2-oxobutyl acetate belongs to the class of organic compounds known as coumarins and derivatives. These are polycyclic aromatic compounds containing a 1-benzopyran moiety with a ketone group at the C2 carbon atom (1-benzopyran-2-one). (+)-Murramarin A is found in Murraya exotica . Based on a literature review very few articles have been published on (1R)-1-[(2S,5'S)-7-methoxy-5'-[(7-methoxy-2-oxo-2H-chromen-8-yl)methyl]-4',4'-dimethylspiro[chromene-2,2'-[1,3]dioxolane]-8-yl]-3-methyl-2-oxobutyl acetate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282219362D          

 42 46  0  0  1  0            999 V2000
   -0.6378   -4.9146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1228   -5.5821    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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  1  2  2  0  0  0  0
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 38 39  2  0  0  0  0
 38 40  1  0  0  0  0
 29 41  1  0  0  0  0
 41 42  1  0  0  0  0
M  END

     RDKit          3D

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M  END


  Mrv1652304282219362D          

 42 46  0  0  1  0            999 V2000
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   -1.7939   -4.0747    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9734   -4.1610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4885   -3.4935    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8240   -2.7398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6445   -2.6536    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3391   -2.0724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6747   -1.3187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4814   -2.1586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3320   -3.5798    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8169   -2.9123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9885   -2.1053    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6239   -2.7408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1294   -3.3211    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9499   -3.2348    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  2  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
  5  7  1  1  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  5 10  1  0  0  0  0
  9 11  1  0  0  0  0
  9 12  1  0  0  0  0
  8 13  1  1  0  0  0
 13 14  1  0  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  2  0  0  0  0
 18 19  1  0  0  0  0
 14 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
 23 24  2  0  0  0  0
 18 24  1  0  0  0  0
 15 25  1  0  0  0  0
 25 26  1  0  0  0  0
  2 27  1  0  0  0  0
 27 28  2  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
  1 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  2  0  0  0  0
 32 34  1  0  0  0  0
 34 35  1  0  0  0  0
 34 36  1  0  0  0  0
 31 37  1  6  0  0  0
 37 38  1  0  0  0  0
 38 39  2  0  0  0  0
 38 40  1  0  0  0  0
 29 41  1  0  0  0  0
 41 42  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0072248

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC=C2C=CC(=O)OC2=C1C[C@@H]1O[C@]2(OC1(C)C)OC1=C(C=CC(OC)=C1[C@@H](OC(C)=O)C(=O)C(C)C)C=C2

> <INCHI_IDENTIFIER>
InChI=1S/C32H34O10/c1-17(2)27(35)30(38-18(3)33)26-23(37-7)12-9-20-14-15-32(41-29(20)26)40-24(31(4,5)42-32)16-21-22(36-6)11-8-19-10-13-25(34)39-28(19)21/h8-15,17,24,30H,16H2,1-7H3/t24-,30+,32-/m0/s1

> <INCHI_KEY>
LFCPZZTYFCUDCA-AYHXQYBJSA-N

> <FORMULA>
C32H34O10

> <MOLECULAR_WEIGHT>
578.614

> <EXACT_MASS>
578.215197295

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
76

> <JCHEM_AVERAGE_POLARIZABILITY>
59.622676137464225

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R)-1-[(2S,5'S)-7-methoxy-5'-[(7-methoxy-2-oxo-2H-chromen-8-yl)methyl]-4',4'-dimethylspiro[chromene-2,2'-[1,3]dioxolane]-8-yl]-3-methyl-2-oxobutyl acetate

> <ALOGPS_LOGP>
4.67

> <JCHEM_LOGP>
5.7471524233333335

> <ALOGPS_LOGS>
-5.86

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.935057278357634

> <JCHEM_PKA_STRONGEST_BASIC>
-4.046530026888798

> <JCHEM_POLAR_SURFACE_AREA>
115.82000000000001

> <JCHEM_REFRACTIVITY>
153.3691

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
7.98e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R)-1-[(2S,5'S)-7-methoxy-5'-[(7-methoxy-2-oxochromen-8-yl)methyl]-4',4'-dimethylspiro[chromene-2,2'-[1,3]dioxolane]-8-yl]-3-methyl-2-oxobutyl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0      -1.191  -9.174   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.096 -10.420   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.469 -11.827   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.062 -11.988   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.967 -10.742   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       0.341  -9.335   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0       1.998  -9.597   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       3.405 -10.224   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.244 -11.755   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       1.737 -12.076   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       3.735 -13.215   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.747 -12.091   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.738  -9.454   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.738  -7.914   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.405  -7.144   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.405  -5.604   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.738  -4.834   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.072  -5.604   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.072  -7.144   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       7.406  -7.914   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       8.739  -7.144   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      10.073  -7.914   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       8.739  -5.604   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       7.406  -4.834   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       2.071  -7.914   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       0.565  -7.594   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -3.627 -10.259   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -4.254  -8.852   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -3.349  -7.606   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -1.817  -7.767   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -0.912  -6.521   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -1.538  -5.114   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      -3.070  -4.953   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0      -0.633  -3.868   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      -1.259  -2.462   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       0.899  -4.029   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0       0.620  -6.682   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0       1.525  -5.436   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0       1.845  -3.930   0.000  0.00  0.00           O+0
HETATM   40  C   UNK     0       3.031  -5.116   0.000  0.00  0.00           C+0
HETATM   41  O   UNK     0      -3.975  -6.199   0.000  0.00  0.00           O+0
HETATM   42  C   UNK     0      -5.506  -6.038   0.000  0.00  0.00           C+0
CONECT    1    2    6   30                                                  
CONECT    2    1    3   27                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6    7   10                                             
CONECT    6    5    1                                                       
CONECT    7    5    8                                                       
CONECT    8    7    9   13                                                  
CONECT    9    8   10   11   12                                             
CONECT   10    9    5                                                       
CONECT   11    9                                                            
CONECT   12    9                                                            
CONECT   13    8   14                                                       
CONECT   14   13   15   19                                                  
CONECT   15   14   16   25                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   24                                                  
CONECT   19   18   14   20                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24                                                       
CONECT   24   23   18                                                       
CONECT   25   15   26                                                       
CONECT   26   25                                                            
CONECT   27    2   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30   41                                                  
CONECT   30   29    1   31                                                  
CONECT   31   30   32   37                                                  
CONECT   32   31   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32   35   36                                                  
CONECT   35   34                                                            
CONECT   36   34                                                            
CONECT   37   31   38                                                       
CONECT   38   37   39   40                                                  
CONECT   39   38                                                            
CONECT   40   38                                                            
CONECT   41   29   42                                                       
CONECT   42   41                                                            
MASTER        0    0    0    0    0    0    0    0   42    0   92    0
END

View in JSmol

Synonyms

Value	Source
(1R)-1-[(2S,5's)-7-Methoxy-5'-[(7-methoxy-2-oxo-2H-chromen-8-yl)methyl]-4',4'-dimethylspiro[chromene-2,2'-[1,3]dioxolane]-8-yl]-3-methyl-2-oxobutyl acetic acid	Generator

Chemical Formula

C₃₂H₃₄O₁₀

Average Mass

578.6140 Da

Monoisotopic Mass

578.21520 Da

IUPAC Name

(1R)-1-[(2S,5'S)-7-methoxy-5'-[(7-methoxy-2-oxo-2H-chromen-8-yl)methyl]-4',4'-dimethylspiro[chromene-2,2'-[1,3]dioxolane]-8-yl]-3-methyl-2-oxobutyl acetate

Traditional Name

(1R)-1-[(2S,5'S)-7-methoxy-5'-[(7-methoxy-2-oxochromen-8-yl)methyl]-4',4'-dimethylspiro[chromene-2,2'-[1,3]dioxolane]-8-yl]-3-methyl-2-oxobutyl acetate

CAS Registry Number

Not Available

SMILES

COC1=CC=C2C=CC(=O)OC2=C1C[C@@H]1O[C@]2(OC1(C)C)OC1=C(C=CC(OC)=C1[C@@H](OC(C)=O)C(=O)C(C)C)C=C2

InChI Identifier

InChI=1S/C32H34O10/c1-17(2)27(35)30(38-18(3)33)26-23(37-7)12-9-20-14-15-32(41-29(20)26)40-24(31(4,5)42-32)16-21-22(36-6)11-8-19-10-13-25(34)39-28(19)21/h8-15,17,24,30H,16H2,1-7H3/t24-,30+,32-/m0/s1

InChI Key

LFCPZZTYFCUDCA-AYHXQYBJSA-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
Murraya exotica	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as coumarins and derivatives. These are polycyclic aromatic compounds containing a 1-benzopyran moiety with a ketone group at the C2 carbon atom (1-benzopyran-2-one).

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Coumarins and derivatives

Sub Class

Not Available

Direct Parent

Coumarins and derivatives

Alternative Parents

Substituents

Coumarin
1-benzopyran
Benzopyran
Anisole
Alpha-acyloxy ketone
Pyranone
Ortho ester
Carboxylic acid orthoester
Alkyl aryl ether
Benzenoid
Pyran
Heteroaromatic compound
Meta-dioxolane
Orthocarboxylic acid derivative
Lactone
Ketone
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Ether
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen 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
logP	4.67	ALOGPS
logP	5.75	ChemAxon
logS	-5.9	ALOGPS
pKa (Strongest Acidic)	10.94	ChemAxon
pKa (Strongest Basic)	-4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	115.82 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	153.37 m³·mol⁻¹	ChemAxon
Polarizability	59.62 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	No	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

163026478

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for (+)-Murramarin A (NP0072248)

MOL for NP0072248 ((+)-Murramarin A)

3D MOL for NP0072248 ((+)-Murramarin A)

3D SDF for NP0072248 ((+)-Murramarin A)

3D-SDF for NP0072248 ((+)-Murramarin A)

PDB for NP0072248 ((+)-Murramarin A)

3D PDB for NP0072248 ((+)-Murramarin A)

SMILES for NP0072248 ((+)-Murramarin A)

INCHI for NP0072248 ((+)-Murramarin A)

Structure for NP0072248 ((+)-Murramarin A)

3D Structure for NP0072248 ((+)-Murramarin A)