NP-MRD: Showing NP-Card for 5’-O-desmethylarmillaribin (NP0332590)

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Record Information

Version

1.0

Created at

2024-02-29 00:05:35 UTC

Updated at

2024-04-19 10:11:57 UTC

NP-MRD ID

NP0332590

Secondary Accession Numbers

None

Natural Product Identification

Common Name

5’-O-desmethylarmillaribin

Description

Not Available

Structure

MOL SDF PDB SMILES InChI


  Mrv2104 02292400052D          

 29 32  0  0  1  0            999 V2000
   -0.4133   -1.6429    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6563   -0.8545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4606   -0.6707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0218   -1.2754    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7788   -2.0638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8261   -1.0916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0691   -0.3032    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8734   -0.1195    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5079    0.3014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7036    0.1177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1423    0.7223    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0950   -0.2498    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7092   -0.4336    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4079    0.0052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7935    0.7345    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3548    1.4332    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7404    2.1625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6180    0.7652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0567    0.0666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6711   -0.6627    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.2455   -1.2549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9862   -0.8915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2702   -1.6661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7863   -0.6901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8695   -0.0748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2323    0.0359    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8467   -0.6934    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0897   -1.4818    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1480   -1.1322    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
  4  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  9 10  2  0  0  0  0
  3 10  1  0  0  0  0
 10 11  1  0  0  0  0
  2 12  1  0  0  0  0
 13 12  1  1  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 15 18  1  0  0  0  0
 18 19  2  0  0  0  0
 20 19  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  1  0  0  0  0
 22 25  1  0  0  0  0
 19 25  1  0  0  0  0
 20 26  1  1  0  0  0
 20 27  1  0  0  0  0
 27 14  1  0  0  0  0
 27 28  1  6  0  0  0
 27 29  1  0  0  0  0
 13 29  1  0  0  0  0
M  END


  Mrv2104 02292400052D          

 29 32  0  0  1  0            999 V2000
   -0.4133   -1.6429    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6563   -0.8545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4606   -0.6707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0218   -1.2754    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7788   -2.0638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8261   -1.0916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0691   -0.3032    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8734   -0.1195    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5079    0.3014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7036    0.1177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1423    0.7223    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0950   -0.2498    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7092   -0.4336    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4079    0.0052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7935    0.7345    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3548    1.4332    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7404    2.1625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6180    0.7652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0567    0.0666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6711   -0.6627    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.2455   -1.2549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9862   -0.8915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2702   -1.6661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7863   -0.6901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8695   -0.0748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2323    0.0359    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8467   -0.6934    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0897   -1.4818    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1480   -1.1322    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
  4  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  9 10  2  0  0  0  0
  3 10  1  0  0  0  0
 10 11  1  0  0  0  0
  2 12  1  0  0  0  0
 13 12  1  1  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 15 18  1  0  0  0  0
 18 19  2  0  0  0  0
 20 19  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  1  0  0  0  0
 22 25  1  0  0  0  0
 19 25  1  0  0  0  0
 20 26  1  1  0  0  0
 20 27  1  0  0  0  0
 27 14  1  0  0  0  0
 27 28  1  6  0  0  0
 27 29  1  0  0  0  0
 13 29  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0332590

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@]12CC(C)(C)CC1=CC(C=O)=C1[C@@H](C[C@]21C)OC(=O)C1=C(C)C=C(O)C=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C23H26O5/c1-12-5-15(25)7-17(26)19(12)21(27)28-18-10-23(4)16-9-22(2,3)8-13(16)6-14(11-24)20(18)23/h5-7,11,16,18,25-26H,8-10H2,1-4H3/t16-,18+,23+/m0/s1

> <INCHI_KEY>
VLOJQZIRWXNZGC-PRCFCKQXSA-N

> <FORMULA>
C23H26O5

> <MOLECULAR_WEIGHT>
382.456

> <EXACT_MASS>
382.178023937

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
54

> <JCHEM_AVERAGE_POLARIZABILITY>
42.1713463429262

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2R,7aS,7bR)-3-formyl-6,6,7b-trimethyl-1H,2H,5H,6H,7H,7aH,7bH-cyclobuta[e]inden-2-yl 2,4-dihydroxy-6-methylbenzoate

> <JCHEM_LOGP>
4.505776754666667

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
10.554610762452878

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.696128839889976

> <JCHEM_PKA_STRONGEST_BASIC>
-4.003049173826859

> <JCHEM_POLAR_SURFACE_AREA>
83.83000000000001

> <JCHEM_REFRACTIVITY>
107.41009999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(2R,7aS,7bR)-3-formyl-6,6,7b-trimethyl-1H,2H,5H,7H,7aH-cyclobuta[e]inden-2-yl 2,4-dihydroxy-6-methylbenzoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 29-FEB-24   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-FEB-24         0                                  
HETATM    1  O   UNK     0      -0.771  -3.067   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      -1.225  -1.595   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.726  -1.252   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -3.774  -2.381   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -3.321  -3.852   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -5.275  -2.038   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -5.729  -0.566   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -7.230  -0.223   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      -4.681   0.563   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -3.180   0.220   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -2.132   1.348   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0      -0.177  -0.466   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       1.324  -0.809   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.628   0.010   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.348   1.371   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.529   2.675   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       3.249   4.037   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       4.887   1.428   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.706   0.124   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.986  -1.237   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       6.058  -2.342   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       7.441  -1.664   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       7.971  -3.110   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       8.934  -1.288   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       7.223  -0.140   0.000  0.00  0.00           C+0
HETATM   26  H   UNK     0       4.167   0.067   0.000  0.00  0.00           H+0
HETATM   27  C   UNK     0       3.447  -1.294   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       3.901  -2.766   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       2.143  -2.113   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   12                                                  
CONECT    3    2    4   10                                                  
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9    3   11                                                  
CONECT   11   10                                                            
CONECT   12    2   13                                                       
CONECT   13   12   14   29                                                  
CONECT   14   13   15   27                                                  
CONECT   15   14   16   18                                                  
CONECT   16   15   17                                                       
CONECT   17   16                                                            
CONECT   18   15   19                                                       
CONECT   19   18   20   25                                                  
CONECT   20   19   21   26   27                                             
CONECT   21   20   22                                                       
CONECT   22   21   23   24   25                                             
CONECT   23   22                                                            
CONECT   24   22                                                            
CONECT   25   22   19                                                       
CONECT   26   20                                                            
CONECT   27   20   14   28   29                                             
CONECT   28   27                                                            
CONECT   29   27   13                                                       
MASTER        0    0    0    0    0    0    0    0   29    0   64    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₃H₂₆O₅

Average Mass

382.4560 Da

Monoisotopic Mass

382.17802 Da

IUPAC Name

(2R,7aS,7bR)-3-formyl-6,6,7b-trimethyl-1H,2H,5H,6H,7H,7aH,7bH-cyclobuta[e]inden-2-yl 2,4-dihydroxy-6-methylbenzoate

Traditional Name

(2R,7aS,7bR)-3-formyl-6,6,7b-trimethyl-1H,2H,5H,7H,7aH-cyclobuta[e]inden-2-yl 2,4-dihydroxy-6-methylbenzoate

CAS Registry Number

Not Available

SMILES

[H][C@]12CC(C)(C)CC1=CC(C=O)=C1[C@@H](C[C@]21C)OC(=O)C1=C(C)C=C(O)C=C1O

InChI Identifier

InChI=1S/C23H26O5/c1-12-5-15(25)7-17(26)19(12)21(27)28-18-10-23(4)16-9-22(2,3)8-13(16)6-14(11-24)20(18)23/h5-7,11,16,18,25-26H,8-10H2,1-4H3/t16-,18+,23+/m0/s1

InChI Key

VLOJQZIRWXNZGC-PRCFCKQXSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
COSY NMR	[¹H, ¹H] NMR Spectrum (2D, 500 MHz, C2D6OS, experimental)	sebastian.pfuetze@helmholtz-hzi.de	Helmholtz-centre for infection research	Sebastian Pfütze	2024-02-29	View Spectrum
ROESY NMR	[¹H, ¹H] NMR Spectrum (2D, 500 MHz, C3D6O, experimental)	sebastian.pfuetze@helmholtz-hzi.de	Helmholtz-centre for infection research	Sebastian Pfütze	2024-02-29	View Spectrum
HSQC NMR	[¹H, ¹³C] NMR Spectrum (2D, 500 MHz, C3D6O, experimental)	sebastian.pfuetze@helmholtz-hzi.de	Helmholtz-centre for infection research	Sebastian Pfütze	2024-02-29	View Spectrum
HMBC NMR	[¹H, ¹³C] NMR Spectrum (2D, 500 MHz, C3D6O, experimental)	sebastian.pfuetze@helmholtz-hzi.de	Helmholtz-centre for infection research	Sebastian Pfütze	2024-02-29	View Spectrum
1D NMR	[¹H, ] NMR Spectrum (2D, 500 MHz, C3D6O, experimental)	sebastian.pfuetze@helmholtz-hzi.de	Helmholtz-centre for infection research	Sebastian Pfütze	2024-02-29	View Spectrum
1D NMR	[¹³C, ] NMR Spectrum (2D, 126 MHz, C3D6O, experimental)	sebastian.pfuetze@helmholtz-hzi.de	Helmholtz-centre for infection research	Sebastian Pfütze	2024-02-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 125.809846744 MHz, C3D6O, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500.283089229 MHz, C3D6O, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

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	4.51	ChemAxon
pKa (Strongest Acidic)	8.7	ChemAxon
pKa (Strongest Basic)	-4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	83.83 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	107.41 m³·mol⁻¹	ChemAxon
Polarizability	42.17 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

Not Available

References

General References

Not Available

Showing NP-Card for 5’-O-desmethylarmillaribin (NP0332590)

MOL for NP0332590 (5’-O-desmethylarmillaribin)

3D MOL for NP0332590 (5’-O-desmethylarmillaribin)

3D SDF for NP0332590 (5’-O-desmethylarmillaribin)

3D-SDF for NP0332590 (5’-O-desmethylarmillaribin)

PDB for NP0332590 (5’-O-desmethylarmillaribin)

3D PDB for NP0332590 (5’-O-desmethylarmillaribin)

SMILES for NP0332590 (5’-O-desmethylarmillaribin)

INCHI for NP0332590 (5’-O-desmethylarmillaribin)

Structure for NP0332590 (5’-O-desmethylarmillaribin)

3D Structure for NP0332590 (5’-O-desmethylarmillaribin)