NP-MRD: Showing NP-Card for Raufiayunesin B (NP0333152)

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Record Information

Version

1.0

Created at

2024-05-11 17:00:54 UTC

Updated at

2024-05-13 01:15:42 UTC

NP-MRD ID

NP0333152

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Raufiayunesin B

Description

Not Available

Structure

MOL SDF PDB SMILES InChI


  Mrv2104 01232319372D          

 30 35  0  0  1  0            999 V2000
    4.9954    1.7778    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7136    1.0024    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2442    0.3707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9624   -0.4047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1500   -0.5483    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7132   -1.2482    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9126   -1.0490    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8546   -0.2260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2749    0.4914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3245    0.3545    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5404    1.1507    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6778   -0.4438    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2802   -1.1563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0467   -1.2624    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0906   -0.5435    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4039   -1.0008    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0266    0.1170    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6729    0.6297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0827   -0.7634    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8262   -1.1129    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1036   -1.5110    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0073   -0.1665    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2640    0.1915    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9457    0.6562    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5587    0.1299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4888   -1.7707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3790   -1.7566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7528   -2.4921    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6194    0.0834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9012    0.8588    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
 10  9  1  0  0  0  0
 10 11  1  1  0  0  0
 12 10  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 15 14  1  0  0  0  0
 15 16  1  6  0  0  0
 15 17  1  0  0  0  0
 10 17  1  0  0  0  0
 17 18  1  0  0  0  0
 12 19  1  1  0  0  0
 20 12  1  0  0  0  0
 20 21  1  1  0  0  0
 22 20  1  0  0  0  0
 22 15  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 22 24  1  1  0  0  0
 23 25  1  1  0  0  0
 20 26  1  0  0  0  0
 26 27  1  0  0  0  0
  7 27  1  0  0  0  0
 27 28  2  0  0  0  0
  5 29  1  0  0  0  0
  8 29  1  0  0  0  0
 29 30  2  0  0  0  0
  2 30  1  0  0  0  0
M  END


  Mrv2104 01232319372D          

 30 35  0  0  1  0            999 V2000
    4.9954    1.7778    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7136    1.0024    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2442    0.3707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9624   -0.4047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1500   -0.5483    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7132   -1.2482    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9126   -1.0490    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8546   -0.2260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2749    0.4914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3245    0.3545    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5404    1.1507    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6778   -0.4438    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2802   -1.1563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0467   -1.2624    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0906   -0.5435    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4039   -1.0008    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0266    0.1170    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6729    0.6297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0827   -0.7634    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8262   -1.1129    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1036   -1.5110    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0073   -0.1665    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2640    0.1915    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9457    0.6562    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5587    0.1299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4888   -1.7707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3790   -1.7566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7528   -2.4921    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6194    0.0834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9012    0.8588    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
 10  9  1  0  0  0  0
 10 11  1  1  0  0  0
 12 10  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 15 14  1  0  0  0  0
 15 16  1  6  0  0  0
 15 17  1  0  0  0  0
 10 17  1  0  0  0  0
 17 18  1  0  0  0  0
 12 19  1  1  0  0  0
 20 12  1  0  0  0  0
 20 21  1  1  0  0  0
 22 20  1  0  0  0  0
 22 15  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 22 24  1  1  0  0  0
 23 25  1  1  0  0  0
 20 26  1  0  0  0  0
 26 27  1  0  0  0  0
  7 27  1  0  0  0  0
 27 28  2  0  0  0  0
  5 29  1  0  0  0  0
  8 29  1  0  0  0  0
 29 30  2  0  0  0  0
  2 30  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0333152

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@]12CC3=C(NC4=CC=C(O)C=C34)C(=O)C[C@]3([H])[C@@]1([H])CO[C@]([H])(N2C)[C@]31O[C@@H]1C

> <INCHI_IDENTIFIER>
InChI=1S/C20H22N2O4/c1-9-20(26-9)14-7-17(24)18-12(11-5-10(23)3-4-15(11)21-18)6-16-13(14)8-25-19(20)22(16)2/h3-5,9,13-14,16,19,21,23H,6-8H2,1-2H3/t9-,13-,14-,16+,19+,20-/m1/s1

> <INCHI_KEY>
GBGNYFQIWHULOT-SLJSTOASSA-N

> <FORMULA>
C20H22N2O4

> <MOLECULAR_WEIGHT>
354.406

> <EXACT_MASS>
354.157957196

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
48

> <JCHEM_AVERAGE_POLARIZABILITY>
36.60622963796173

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1'S,2S,3R,14'R,16'S,19'R)-6'-hydroxy-3,20'-dimethyl-17'-oxa-10',20'-diazaspiro[oxirane-2,15'-pentacyclo[14.3.1.0^{3,11}.0^{4,9}.0^{14,19}]icosane]-3'(11'),4',6',8'-tetraen-12'-one

> <JCHEM_LOGP>
1.6033000030000002

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.444130578635738

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.547966304452293

> <JCHEM_PKA_STRONGEST_BASIC>
5.035966895982059

> <JCHEM_POLAR_SURFACE_AREA>
78.09

> <JCHEM_REFRACTIVITY>
94.88330000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1'S,2S,3R,14'R,16'S,19'R)-6'-hydroxy-3,20'-dimethyl-17'-oxa-10',20'-diazaspiro[oxirane-2,15'-pentacyclo[14.3.1.0^{3,11}.0^{4,9}.0^{14,19}]icosane]-3'(11'),4',6',8'-tetraen-12'-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 23-JAN-23   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-JAN-23         0                                  
HETATM    1  O   UNK     0       9.325   3.319   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       8.799   1.871   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       9.789   0.692   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.263  -0.755   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.747  -1.024   0.000  0.00  0.00           C+0
HETATM    6  N   UNK     0       6.931  -2.330   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0       5.437  -1.958   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.329  -0.422   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.247   0.917   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.472   0.662   0.000  0.00  0.00           C+0
HETATM   11  H   UNK     0       2.875   2.148   0.000  0.00  0.00           H+0
HETATM   12  C   UNK     0       1.265  -0.828   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.390  -2.158   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       3.821  -2.357   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       3.902  -1.015   0.000  0.00  0.00           C+0
HETATM   16  H   UNK     0       2.621  -1.868   0.000  0.00  0.00           H+0
HETATM   17  N   UNK     0       3.783   0.218   0.000  0.00  0.00           N+0
HETATM   18  C   UNK     0       4.990   1.175   0.000  0.00  0.00           C+0
HETATM   19  H   UNK     0      -0.154  -1.425   0.000  0.00  0.00           H+0
HETATM   20  C   UNK     0       1.542  -2.077   0.000  0.00  0.00           C+0
HETATM   21  H   UNK     0       0.193  -2.821   0.000  0.00  0.00           H+0
HETATM   22  C   UNK     0       1.880  -0.311   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       0.493   0.357   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       1.765   1.225   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      -1.043   0.242   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       2.779  -3.305   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       4.441  -3.279   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       5.139  -4.652   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       6.756   0.156   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       7.282   1.603   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   30                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   29                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   27                                                  
CONECT    8    7    9   29                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   12   17                                             
CONECT   11   10                                                            
CONECT   12   10   13   19   20                                             
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   17   22                                             
CONECT   16   15                                                            
CONECT   17   15   10   18                                                  
CONECT   18   17                                                            
CONECT   19   12                                                            
CONECT   20   12   21   22   26                                             
CONECT   21   20                                                            
CONECT   22   20   15   23   24                                             
CONECT   23   22   24   25                                                  
CONECT   24   23   22                                                       
CONECT   25   23                                                            
CONECT   26   20   27                                                       
CONECT   27   26    7   28                                                  
CONECT   28   27                                                            
CONECT   29    5    8   30                                                  
CONECT   30   29    2                                                       
MASTER        0    0    0    0    0    0    0    0   30    0   70    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₀H₂₂N₂O₄

Average Mass

354.4060 Da

Monoisotopic Mass

354.15796 Da

IUPAC Name

(1'S,2S,3R,14'R,16'S,19'R)-6'-hydroxy-3,20'-dimethyl-17'-oxa-10',20'-diazaspiro[oxirane-2,15'-pentacyclo[14.3.1.0^{3,11}.0^{4,9}.0^{14,19}]icosane]-3'(11'),4',6',8'-tetraen-12'-one

Traditional Name

(1'S,2S,3R,14'R,16'S,19'R)-6'-hydroxy-3,20'-dimethyl-17'-oxa-10',20'-diazaspiro[oxirane-2,15'-pentacyclo[14.3.1.0^{3,11}.0^{4,9}.0^{14,19}]icosane]-3'(11'),4',6',8'-tetraen-12'-one

CAS Registry Number

Not Available

SMILES

[H][C@]12CC3=C(NC4=CC=C(O)C=C34)C(=O)C[C@]3([H])[C@@]1([H])CO[C@]([H])(N2C)[C@]31O[C@@H]1C

InChI Identifier

InChI=1S/C20H22N2O4/c1-9-20(26-9)14-7-17(24)18-12(11-5-10(23)3-4-15(11)21-18)6-16-13(14)8-25-19(20)22(16)2/h3-5,9,13-14,16,19,21,23H,6-8H2,1-2H3/t9-,13-,14-,16+,19+,20-/m1/s1

InChI Key

GBGNYFQIWHULOT-SLJSTOASSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
ROESY NMR	[¹H, ¹H] NMR Spectrum (2D, 600 MHz, CDCl3, experimental)	qinmalong@163.com	Not Available	Not Available	2024-05-11	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, C2D6OS, experimental)	qinmalong@163.com	Not Available	Not Available	2024-05-11	View Spectrum
COSY NMR	[¹H, ¹H] NMR Spectrum (2D, 600 MHz, CDCl3, experimental)	qinmalong@163.com	Not Available	Not Available	2024-05-11	View Spectrum
HMBC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, CDCl3, experimental)	qinmalong@163.com	Not Available	Not Available	2024-05-11	View Spectrum
HSQC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, CDCl3, experimental)	qinmalong@163.com	Not Available	Not Available	2024-05-11	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CDCl3, experimental)	qinmalong@163.com	Not Available	Not Available	2024-05-11	View Spectrum
1D_DEPT NMR	¹³C NMR Spectrum (1D, 151 MHz, CDCl3, experimental)	qinmalong@163.com	Not Available	Not Available	2024-05-11	View Spectrum
1D_DEPT NMR	¹³C NMR Spectrum (1D, 151 MHz, CDCl3, experimental)	qinmalong@163.com	Not Available	Not Available	2024-05-11	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, CDCl3, experimental)	qinmalong@163.com	Not Available	Not Available	2024-05-11	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
yunnanensis		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	1.6	ChemAxon
pKa (Strongest Acidic)	9.55	ChemAxon
pKa (Strongest Basic)	5.04	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	78.09 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	94.88 m³·mol⁻¹	ChemAxon
Polarizability	36.61 Å³	ChemAxon
Number of Rings	6	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 Raufiayunesin B (NP0333152)

MOL for NP0333152 (Raufiayunesin B)

3D MOL for NP0333152 (Raufiayunesin B)

3D SDF for NP0333152 (Raufiayunesin B)

3D-SDF for NP0333152 (Raufiayunesin B)

PDB for NP0333152 (Raufiayunesin B)

3D PDB for NP0333152 (Raufiayunesin B)

SMILES for NP0333152 (Raufiayunesin B)

INCHI for NP0333152 (Raufiayunesin B)

Structure for NP0333152 (Raufiayunesin B)

3D Structure for NP0333152 (Raufiayunesin B)