NP-MRD: Showing NP-Card for Uvarialeptone A (NP0333240)

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Record Information

Version

2.0

Created at

2024-05-13 01:45:15 UTC

Updated at

2024-09-16 20:03:41 UTC

NP-MRD ID

NP0333240

Natural Product DOI

https://doi.org/10.57994/2576

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Uvarialeptone A

Description

Not Available

Structure

MOL SDF PDB SMILES InChI


  Mrv2104 01252304212D          

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> <DATABASE_ID>
NP0333240

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC2=C(O[C@@]3(CC(=O)\C(=C(/O)[C@H]4[C@H]([C@@H]([C@@H]4C4=CC=CC=C4)C(\O)=C4\C(=O)C[C@]5(OC)OC6=C(C[C@]5(OC)C4=O)C=C(OC)C=C6)C4=CC=CC=C4)C(=O)[C@@]3(C2)OC)OC)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C50H48O14/c1-57-31-17-19-35-29(21-31)23-47(59-3)45(55)39(33(51)25-49(47,61-5)63-35)43(53)41-37(27-13-9-7-10-14-27)42(38(41)28-15-11-8-12-16-28)44(54)40-34(52)26-50(62-6)48(60-4,46(40)56)24-30-22-32(58-2)18-20-36(30)64-50/h7-22,37-38,41-42,53-54H,23-26H2,1-6H3/b43-39+,44-40+/t37-,38-,41-,42-,47-,48+,49-,50+

> <INCHI_KEY>
RLUPCOVCBSKEGP-NUTSQRBNSA-N

> <FORMULA>
C50H48O14

> <MOLECULAR_WEIGHT>
872.92

> <EXACT_MASS>
872.304406226

> <JCHEM_ACCEPTOR_COUNT>
14

> <JCHEM_ATOM_COUNT>
112

> <JCHEM_AVERAGE_POLARIZABILITY>
88.74551483309808

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2E,4aS,9aS)-2-{[(1R,2R,3S,4S)-3-{[(2E,4aR,9aR)-4a,7,9a-trimethoxy-1,3-dioxo-2,3,4,4a,9,9a-hexahydro-1H-xanthen-2-ylidene](hydroxy)methyl}-2,4-diphenylcyclobutyl](hydroxy)methylidene}-4a,7,9a-trimethoxy-2,3,4,4a,9,9a-hexahydro-1H-xanthene-1,3-dione

> <JCHEM_LOGP>
7.50600574

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
9

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
2.969576491014081

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.331163661857754

> <JCHEM_PKA_STRONGEST_BASIC>
-3.938568247775518

> <JCHEM_POLAR_SURFACE_AREA>
182.57999999999998

> <JCHEM_REFRACTIVITY>
232.0361999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(2E,4aS,9aS)-2-{[(1R,2R,3S,4S)-3-{[(2E,4aR,9aR)-4a,7,9a-trimethoxy-1,3-dioxo-4,9-dihydroxanthen-2-ylidene](hydroxy)methyl}-2,4-diphenylcyclobutyl](hydroxy)methylidene}-4a,7,9a-trimethoxy-4,9-dihydroxanthene-1,3-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 25-JAN-23   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   25-JAN-23         0                                  
HETATM    1  O   UNK     0       0.000  -4.620   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.366  -7.809   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.019  -8.229   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.733  -6.685   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.216  -6.475   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.043  -8.019   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.273  -9.353   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.733  -9.353   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.334  -9.108   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.965 -10.479   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       3.298 -11.249   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       0.631 -11.249   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.000 -12.958   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.334 -12.188   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.334 -10.648   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       2.667  -9.878   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       2.667  -8.338   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.001  -7.568   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       3.370  -6.197   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       2.667  -5.258   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       4.001  -6.028   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       5.335  -5.258   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       1.334  -6.028   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       1.334  -7.568   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -0.210  -8.394   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       2.667 -11.418   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       2.667 -12.958   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       0.000  -9.878   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       0.000 -11.418   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      -1.965 -12.357   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -1.334 -10.648   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      -1.334  -9.108   0.000  0.00  0.00           O+0
HETATM   35  O   UNK     0      -1.334 -12.188   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0       0.245  -8.019   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      -1.295  -8.019   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      -2.065  -9.353   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      -3.605  -9.353   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      -4.375  -8.019   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      -3.605  -6.685   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0      -2.065  -6.685   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   47  O   UNK     0       6.668  -2.310   0.000  0.00  0.00           O+0
HETATM   48  C   UNK     0       8.002  -3.080   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0       9.336  -2.310   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0      10.669  -3.080   0.000  0.00  0.00           C+0
HETATM   51  C   UNK     0      10.669  -4.620   0.000  0.00  0.00           C+0
HETATM   52  O   UNK     0      12.003  -5.390   0.000  0.00  0.00           O+0
HETATM   53  C   UNK     0      13.337  -4.620   0.000  0.00  0.00           C+0
HETATM   54  C   UNK     0       9.336  -5.390   0.000  0.00  0.00           C+0
HETATM   55  C   UNK     0       8.002  -4.620   0.000  0.00  0.00           C+0
HETATM   56  C   UNK     0       6.668  -5.390   0.000  0.00  0.00           C+0
HETATM   57  O   UNK     0       5.335  -1.540   0.000  0.00  0.00           O+0
HETATM   58  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   59  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   60  O   UNK     0       5.335  -6.160   0.000  0.00  0.00           O+0
HETATM   61  C   UNK     0       6.668  -6.930   0.000  0.00  0.00           C+0
HETATM   62  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM   63  O   UNK     0       4.001  -6.930   0.000  0.00  0.00           O+0
HETATM   64  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   43                                                  
CONECT    3    2    4   36                                                  
CONECT    4    3    5   11                                                  
CONECT    5    4    6   10                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9    5                                                       
CONECT   11    4   12   36                                                  
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15   33                                                  
CONECT   15   14   16   35                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   28   30                                             
CONECT   18   17   19                                                       
CONECT   19   18   20   26                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23   25                                                  
CONECT   23   22   24                                                       
CONECT   24   23                                                            
CONECT   25   22   26                                                       
CONECT   26   19   25   27                                                  
CONECT   27   26   30                                                       
CONECT   28   17   29                                                       
CONECT   29   28                                                            
CONECT   30   17   27   31   33                                             
CONECT   31   30   32                                                       
CONECT   32   31                                                            
CONECT   33   30   14   34                                                  
CONECT   34   33                                                            
CONECT   35   15                                                            
CONECT   36   11    3   37                                                  
CONECT   37   36   38   42                                                  
CONECT   38   37   39                                                       
CONECT   39   38   40                                                       
CONECT   40   39   41                                                       
CONECT   41   40   42                                                       
CONECT   42   41   37                                                       
CONECT   43    2   44   62                                                  
CONECT   44   43   45   64                                                  
CONECT   45   44   46                                                       
CONECT   46   45   47   57   59                                             
CONECT   47   46   48                                                       
CONECT   48   47   49   55                                                  
CONECT   49   48   50                                                       
CONECT   50   49   51                                                       
CONECT   51   50   52   54                                                  
CONECT   52   51   53                                                       
CONECT   53   52                                                            
CONECT   54   51   55                                                       
CONECT   55   48   54   56                                                  
CONECT   56   55   59                                                       
CONECT   57   46   58                                                       
CONECT   58   57                                                            
CONECT   59   46   56   60   62                                             
CONECT   60   59   61                                                       
CONECT   61   60                                                            
CONECT   62   59   43   63                                                  
CONECT   63   62                                                            
CONECT   64   44                                                            
MASTER        0    0    0    0    0    0    0    0   64    0  144    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₅₀H₄₈O₁₄

Average Mass

872.9200 Da

Monoisotopic Mass

872.30441 Da

IUPAC Name

(2E,4aS,9aS)-2-{[(1R,2R,3S,4S)-3-{[(2E,4aR,9aR)-4a,7,9a-trimethoxy-1,3-dioxo-2,3,4,4a,9,9a-hexahydro-1H-xanthen-2-ylidene](hydroxy)methyl}-2,4-diphenylcyclobutyl](hydroxy)methylidene}-4a,7,9a-trimethoxy-2,3,4,4a,9,9a-hexahydro-1H-xanthene-1,3-dione

Traditional Name

(2E,4aS,9aS)-2-{[(1R,2R,3S,4S)-3-{[(2E,4aR,9aR)-4a,7,9a-trimethoxy-1,3-dioxo-4,9-dihydroxanthen-2-ylidene](hydroxy)methyl}-2,4-diphenylcyclobutyl](hydroxy)methylidene}-4a,7,9a-trimethoxy-4,9-dihydroxanthene-1,3-dione

CAS Registry Number

Not Available

SMILES

COC1=CC2=C(O[C@@]3(CC(=O)\C(=C(/O)[C@H]4[C@H]([C@@H]([C@@H]4C4=CC=CC=C4)C(\O)=C4\C(=O)C[C@]5(OC)OC6=C(C[C@]5(OC)C4=O)C=C(OC)C=C6)C4=CC=CC=C4)C(=O)[C@@]3(C2)OC)OC)C=C1

InChI Identifier

InChI=1S/C50H48O14/c1-57-31-17-19-35-29(21-31)23-47(59-3)45(55)39(33(51)25-49(47,61-5)63-35)43(53)41-37(27-13-9-7-10-14-27)42(38(41)28-15-11-8-12-16-28)44(54)40-34(52)26-50(62-6)48(60-4,46(40)56)24-30-22-32(58-2)18-20-36(30)64-50/h7-22,37-38,41-42,53-54H,23-26H2,1-6H3/b43-39+,44-40+/t37-,38-,41-,42-,47-,48+,49-,50+

InChI Key

RLUPCOVCBSKEGP-NUTSQRBNSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
NOESY NMR	[¹H, ¹H] NMR Spectrum (2D, 500 MHz, CDCl3, experimental)	surat.lap@mfu.ac.th	Mae Fah Luang University	Surat Laphookhieo	2024-05-13	View Spectrum
HSQC NMR	[¹H, ¹³C] NMR Spectrum (2D, 500 MHz, CDCl3, experimental)	surat.lap@mfu.ac.th	Mae Fah Luang University	Surat Laphookhieo	2024-05-13	View Spectrum
HMBC NMR	[¹H, ¹³C] NMR Spectrum (2D, 500 MHz, CDCl3, experimental)	surat.lap@mfu.ac.th	Mae Fah Luang University	Surat Laphookhieo	2024-05-13	View Spectrum
COSY NMR	[¹H, ¹H] NMR Spectrum (2D, 500 MHz, CDCl3, experimental)	surat.lap@mfu.ac.th	Mae Fah Luang University	Surat Laphookhieo	2024-05-13	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CDCl3, experimental)	surat.lap@mfu.ac.th	Mae Fah Luang University	Surat Laphookhieo	2024-05-13	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, CDCl3, experimental)	surat.lap@mfu.ac.th	Mae Fah Luang University	Surat Laphookhieo	2024-05-13	View Spectrum

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
leptopoda		Not Available

Chemical Taxonomy

Classification

Not classified

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	7.51	ChemAxon
pKa (Strongest Acidic)	2.33	ChemAxon
pKa (Strongest Basic)	-3.9	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	14	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	182.58 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	232.04 m³·mol⁻¹	ChemAxon
Polarizability	88.75 Å³	ChemAxon
Number of Rings	9	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

Not Available

References

General References

Not Available

Showing NP-Card for Uvarialeptone A (NP0333240)

MOL for NP0333240 (Uvarialeptone A)

3D MOL for NP0333240 (Uvarialeptone A)

3D SDF for NP0333240 (Uvarialeptone A)

3D-SDF for NP0333240 (Uvarialeptone A)

PDB for NP0333240 (Uvarialeptone A)

3D PDB for NP0333240 (Uvarialeptone A)

SMILES for NP0333240 (Uvarialeptone A)

INCHI for NP0333240 (Uvarialeptone A)

Structure for NP0333240 (Uvarialeptone A)

3D Structure for NP0333240 (Uvarialeptone A)