NP-MRD: Showing NP-Card for hypocrellin A (NP0029581)

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Record Information

Version

2.0

Created at

2021-06-19 21:10:33 UTC

Updated at

2021-06-29 23:57:02 UTC

NP-MRD ID

NP0029581

Secondary Accession Numbers

None

Natural Product Identification

Common Name

hypocrellin A

Provided By

JEOL Database JEOL Logo

Description

(12R,13S)-12-acetyl-9,13,17-trihydroxy-5,10,16,21-tetramethoxy-13-methylhexacyclo[13.8.0.0²,¹¹.0³,⁸.0⁴,²².0¹⁸,²³]Tricosa-1(15),2(11),3(8),4(22),5,9,16,18(23),20-nonaene-7,19-dione belongs to the class of organic compounds known as perylenequinones. These are heterocyclic compounds characterized by two 8-hydroxy-1,4-dihydronaphthalen-1-one moieties joined together one or two CC-bonds. hypocrellin A is found in Ascomycete Shiraia bambusicola and Shiraia bambusicola. hypocrellin A was first documented in 2006 (Fang, L.-Z., et al.). Based on a literature review very few articles have been published on (12R,13S)-12-acetyl-9,13,17-trihydroxy-5,10,16,21-tetramethoxy-13-methylhexacyclo[13.8.0.0²,¹¹.0³,⁸.0⁴,²².0¹⁸,²³]Tricosa-1(15),2(11),3(8),4(22),5,9,16,18(23),20-nonaene-7,19-dione.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306192123103D          

 66 71  0  0  0  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652306192123103D          

 66 71  0  0  0  0            999 V2000
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M  END
> <DATABASE_ID>
NP0029581

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C2C(=O)C([H])=C(OC([H])([H])[H])C3=C4C(OC([H])([H])[H])=C([H])C(=O)C5=C(O[H])C(OC([H])([H])[H])=C6C(=C45)C(=C23)C(=C1OC([H])([H])[H])C([H])([H])[C@@](O[H])(C([H])([H])[H])[C@]6([H])C(=O)C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C30H26O10/c1-10(31)25-24-22-16-11(9-30(25,2)36)28(39-5)26(34)17-12(32)7-14(37-3)19(21(16)17)20-15(38-4)8-13(33)18(23(20)22)27(35)29(24)40-6/h7-8,25,34-36H,9H2,1-6H3/t25-,30+/m1/s1

> <INCHI_KEY>
VANSZAOQCMTTPB-RNAHPLFWSA-N

> <FORMULA>
C30H26O10

> <MOLECULAR_WEIGHT>
546.528

> <EXACT_MASS>
546.152597037

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
66

> <JCHEM_AVERAGE_POLARIZABILITY>
55.294203912355954

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(12R,13S)-12-acetyl-9,13,17-trihydroxy-5,10,16,21-tetramethoxy-13-methylhexacyclo[13.8.0.0^{2,11}.0^{3,8}.0^{4,22}.0^{18,23}]tricosa-1(15),2(11),3(8),4(22),5,9,16,18(23),20-nonaene-7,19-dione

> <ALOGPS_LOGP>
3.17

> <JCHEM_LOGP>
2.5457756676666676

> <ALOGPS_LOGS>
-4.51

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
7.741481393330778

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.138765067581505

> <JCHEM_PKA_STRONGEST_BASIC>
3.6528176008479503

> <JCHEM_POLAR_SURFACE_AREA>
148.82

> <JCHEM_REFRACTIVITY>
147.48149999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.70e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(12R,13S)-12-acetyl-9,13,17-trihydroxy-5,10,16,21-tetramethoxy-13-methylhexacyclo[13.8.0.0^{2,11}.0^{3,8}.0^{4,22}.0^{18,23}]tricosa-1(15),2(11),3(8),4(22),5,9,16,18(23),20-nonaene-7,19-dione

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 66 71  0  0  0  0  0  0  0  0999 V2000
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 17 50  1  0
 17 51  1  0
 12 46  1  0
 12 47  1  0
 12 48  1  0
 23 53  1  0
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 26 55  1  0
 26 56  1  0
  1 41  1  0
  1 42  1  0
  1 43  1  0
  5 44  1  0
 31 57  1  0
 31 58  1  0
 34 62  1  0
 33 59  1  0
 33 60  1  0
 33 61  1  0
 37 64  1  0
 37 65  1  0
 37 66  1  0
M  END

HEADER    PROTEIN                                 19-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-JUN-21         0                                  
HETATM    1  C   UNK     0       3.106  -5.497   0.702  0.00  0.00           C+0
HETATM    2  O   UNK     0       1.926  -5.009   0.063  0.00  0.00           O+0
HETATM    3  C   UNK     0       1.481  -3.828   0.601  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.091  -3.720   1.932  0.00  0.00           C+0
HETATM    5  O   UNK     0       1.182  -4.829   2.735  0.00  0.00           O+0
HETATM    6  C   UNK     0       0.557  -2.510   2.390  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.053  -2.421   3.777  0.00  0.00           C+0
HETATM    8  O   UNK     0       0.008  -3.405   4.508  0.00  0.00           O+0
HETATM    9  C   UNK     0      -0.332  -1.098   4.288  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.405  -0.040   3.469  0.00  0.00           C+0
HETATM   11  O   UNK     0      -0.550   1.269   3.883  0.00  0.00           O+0
HETATM   12  C   UNK     0      -0.772   1.523   5.265  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.199  -0.205   1.999  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.577   0.770   1.047  0.00  0.00           C+0
HETATM   15  C   UNK     0      -1.701   1.729   1.263  0.00  0.00           C+0
HETATM   16  O   UNK     0      -2.630   1.322   2.199  0.00  0.00           O+0
HETATM   17  C   UNK     0      -3.726   2.181   2.488  0.00  0.00           C+0
HETATM   18  C   UNK     0      -1.810   2.828   0.504  0.00  0.00           C+0
HETATM   19  C   UNK     0      -0.894   3.057  -0.620  0.00  0.00           C+0
HETATM   20  O   UNK     0      -0.922   4.117  -1.239  0.00  0.00           O+0
HETATM   21  C   UNK     0       0.008   1.955  -1.021  0.00  0.00           C+0
HETATM   22  C   UNK     0       0.771   2.086  -2.189  0.00  0.00           C+0
HETATM   23  O   UNK     0       0.696   3.205  -2.980  0.00  0.00           O+0
HETATM   24  C   UNK     0       1.688   1.093  -2.523  0.00  0.00           C+0
HETATM   25  O   UNK     0       2.548   1.191  -3.588  0.00  0.00           O+0
HETATM   26  C   UNK     0       1.927   1.534  -4.826  0.00  0.00           C+0
HETATM   27  C   UNK     0       1.841  -0.032  -1.686  0.00  0.00           C+0
HETATM   28  C   UNK     0       0.966  -0.244  -0.563  0.00  0.00           C+0
HETATM   29  C   UNK     0       0.928  -1.449   0.221  0.00  0.00           C+0
HETATM   30  C   UNK     0       1.335  -2.731  -0.268  0.00  0.00           C+0
HETATM   31  C   UNK     0       1.470  -2.954  -1.766  0.00  0.00           C+0
HETATM   32  C   UNK     0       2.719  -2.346  -2.417  0.00  0.00           C+0
HETATM   33  C   UNK     0       2.482  -2.299  -3.939  0.00  0.00           C+0
HETATM   34  O   UNK     0       3.828  -3.246  -2.257  0.00  0.00           O+0
HETATM   35  C   UNK     0       3.072  -0.933  -1.897  0.00  0.00           C+0
HETATM   36  C   UNK     0       3.985  -0.913  -0.655  0.00  0.00           C+0
HETATM   37  C   UNK     0       4.567   0.423  -0.255  0.00  0.00           C+0
HETATM   38  O   UNK     0       4.257  -1.927  -0.006  0.00  0.00           O+0
HETATM   39  C   UNK     0       0.443  -1.379   1.549  0.00  0.00           C+0
HETATM   40  C   UNK     0       0.111   0.821  -0.186  0.00  0.00           C+0
HETATM   41  H   UNK     0       3.720  -4.697   1.132  0.00  0.00           H+0
HETATM   42  H   UNK     0       3.707  -6.007  -0.057  0.00  0.00           H+0
HETATM   43  H   UNK     0       2.843  -6.234   1.467  0.00  0.00           H+0
HETATM   44  H   UNK     0       0.765  -4.630   3.602  0.00  0.00           H+0
HETATM   45  H   UNK     0      -0.474  -1.048   5.359  0.00  0.00           H+0
HETATM   46  H   UNK     0      -1.687   1.031   5.612  0.00  0.00           H+0
HETATM   47  H   UNK     0      -0.901   2.602   5.392  0.00  0.00           H+0
HETATM   48  H   UNK     0       0.092   1.214   5.863  0.00  0.00           H+0
HETATM   49  H   UNK     0      -4.324   1.709   3.273  0.00  0.00           H+0
HETATM   50  H   UNK     0      -4.365   2.310   1.609  0.00  0.00           H+0
HETATM   51  H   UNK     0      -3.376   3.147   2.866  0.00  0.00           H+0
HETATM   52  H   UNK     0      -2.596   3.563   0.611  0.00  0.00           H+0
HETATM   53  H   UNK     0       0.097   3.861  -2.556  0.00  0.00           H+0
HETATM   54  H   UNK     0       0.888   1.192  -4.890  0.00  0.00           H+0
HETATM   55  H   UNK     0       2.488   1.036  -5.624  0.00  0.00           H+0
HETATM   56  H   UNK     0       1.998   2.611  -4.999  0.00  0.00           H+0
HETATM   57  H   UNK     0       0.559  -2.544  -2.227  0.00  0.00           H+0
HETATM   58  H   UNK     0       1.427  -4.025  -2.001  0.00  0.00           H+0
HETATM   59  H   UNK     0       2.282  -3.303  -4.332  0.00  0.00           H+0
HETATM   60  H   UNK     0       3.375  -1.939  -4.464  0.00  0.00           H+0
HETATM   61  H   UNK     0       1.640  -1.653  -4.206  0.00  0.00           H+0
HETATM   62  H   UNK     0       4.016  -3.301  -1.295  0.00  0.00           H+0
HETATM   63  H   UNK     0       3.742  -0.498  -2.652  0.00  0.00           H+0
HETATM   64  H   UNK     0       5.343   0.270   0.501  0.00  0.00           H+0
HETATM   65  H   UNK     0       3.787   1.061   0.166  0.00  0.00           H+0
HETATM   66  H   UNK     0       5.024   0.903  -1.123  0.00  0.00           H+0
CONECT    1    2   41   42   43                                             
CONECT    2    3    1                                                       
CONECT    3    2   30    4                                                  
CONECT    4    6    5    3                                                  
CONECT    5    4   44                                                       
CONECT    6    4    7   39                                                  
CONECT    7    8    9    6                                                  
CONECT    8    7                                                            
CONECT    9   10    7   45                                                  
CONECT   10    9   11   13                                                  
CONECT   11   10   12                                                       
CONECT   12   11   46   47   48                                             
CONECT   13   14   10   39                                                  
CONECT   14   13   40   15                                                  
CONECT   15   16   14   18                                                  
CONECT   16   15   17                                                       
CONECT   17   16   49   50   51                                             
CONECT   18   15   19   52                                                  
CONECT   19   20   18   21                                                  
CONECT   20   19                                                            
CONECT   21   40   22   19                                                  
CONECT   22   21   24   23                                                  
CONECT   23   22   53                                                       
CONECT   24   22   27   25                                                  
CONECT   25   24   26                                                       
CONECT   26   25   54   55   56                                             
CONECT   27   24   35   28                                                  
CONECT   28   29   40   27                                                  
CONECT   29   39   28   30                                                  
CONECT   30   31   29    3                                                  
CONECT   31   30   32   57   58                                             
CONECT   32   31   35   34   33                                             
CONECT   33   32   59   60   61                                             
CONECT   34   32   62                                                       
CONECT   35   27   32   36   63                                             
CONECT   36   35   37   38                                                  
CONECT   37   36   64   65   66                                             
CONECT   38   36                                                            
CONECT   39   29   13    6                                                  
CONECT   40   21   14   28                                                  
CONECT   41    1                                                            
CONECT   42    1                                                            
CONECT   43    1                                                            
CONECT   44    5                                                            
CONECT   45    9                                                            
CONECT   46   12                                                            
CONECT   47   12                                                            
CONECT   48   12                                                            
CONECT   49   17                                                            
CONECT   50   17                                                            
CONECT   51   17                                                            
CONECT   52   18                                                            
CONECT   53   23                                                            
CONECT   54   26                                                            
CONECT   55   26                                                            
CONECT   56   26                                                            
CONECT   57   31                                                            
CONECT   58   31                                                            
CONECT   59   33                                                            
CONECT   60   33                                                            
CONECT   61   33                                                            
CONECT   62   34                                                            
CONECT   63   35                                                            
CONECT   64   37                                                            
CONECT   65   37                                                            
CONECT   66   37                                                            
MASTER        0    0    0    0    0    0    0    0   66    0  142    0
END

RDKit          3D

66 71  0  0  0  0  0  0  0  0999 V2000
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    3.7874    1.0614    0.1658 H   0  0  0  0  0  0  0  0  0  0  0  0
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 40 21  1  0
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  1 41  1  0
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 37 64  1  0
 37 65  1  0
 37 66  1  0
M  END

View in JSmol

Synonyms

Value	Source
1-Acetyl-2,3-dihydro-2,6,11-trihydroxy-4,8,9,13-tetramethoxy-2-methyl-1H-cyclohepta(ghi)perylene-5,12-dione	MeSH
Hypocrellin	MeSH

Chemical Formula

C₃₀H₂₆O₁₀

Average Mass

546.5280 Da

Monoisotopic Mass

546.15260 Da

IUPAC Name

(12R,13S)-12-acetyl-9,13,17-trihydroxy-5,10,16,21-tetramethoxy-13-methylhexacyclo[13.8.0.0^{2,11}.0^{3,8}.0^{4,22}.0^{18,23}]tricosa-1(15),2(11),3(8),4(22),5,9,16,18(23),20-nonaene-7,19-dione

Traditional Name

(12R,13S)-12-acetyl-9,13,17-trihydroxy-5,10,16,21-tetramethoxy-13-methylhexacyclo[13.8.0.0^{2,11}.0^{3,8}.0^{4,22}.0^{18,23}]tricosa-1(15),2(11),3(8),4(22),5,9,16,18(23),20-nonaene-7,19-dione

CAS Registry Number

Not Available

SMILES

[H]OC1=C2C(=O)C([H])=C(OC([H])([H])[H])C3=C4C(OC([H])([H])[H])=C([H])C(=O)C5=C(O[H])C(OC([H])([H])[H])=C6C(=C45)C(=C23)C(=C1OC([H])([H])[H])C([H])([H])[C@@](O[H])(C([H])([H])[H])[C@]6([H])C(=O)C([H])([H])[H]

InChI Identifier

InChI=1S/C30H26O10/c1-10(31)25-24-22-16-11(9-30(25,2)36)28(39-5)26(34)17-12(32)7-14(37-3)19(21(16)17)20-15(38-4)8-13(33)18(23(20)22)27(35)29(24)40-6/h7-8,25,34-36H,9H2,1-6H3/t25-,30+/m1/s1

InChI Key

VANSZAOQCMTTPB-RNAHPLFWSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, CDCl₃, 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

Species Name	Source	Reference
Ascomycete Shiraia bambusicola	JEOL database	Fang, L.-Z., et al, J. Antibiotics 59, 351 (2006)
Shiraia bambusicola	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as perylenequinones. These are heterocyclic compounds characterized by two 8-hydroxy-1,4-dihydronaphthalen-1-one moieties joined together one or two CC-bonds.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Perylenequinones

Sub Class

Not Available

Direct Parent

Perylenequinones

Alternative Parents

Substituents

Perylenequinone
Phenanthrol
Anthracene
Phenanthrene
2-naphthol
1-naphthol
Anisole
Phenol ether
Alkyl aryl ether
Phenol
Vinylogous ester
Vinylogous acid
Tertiary alcohol
Ketone
Ether
Polyol
Alcohol
Carbonyl group
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Organooxygen compound
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic 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	3.17	ALOGPS
logP	2.55	ChemAxon
logS	-4.5	ALOGPS
pKa (Strongest Acidic)	7.14	ChemAxon
pKa (Strongest Basic)	3.65	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	148.82 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	147.48 m³·mol⁻¹	ChemAxon
Polarizability	55.29 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	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

75548422

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

14502645

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Fang, L.-Z., et al. (2006). Fang, L.-Z., et al, J. Antibiotics 59, 351 (2006). J. Antibiotics.

Showing NP-Card for hypocrellin A (NP0029581)

MOL for NP0029581 (hypocrellin A)

3D MOL for NP0029581 (hypocrellin A)

3D SDF for NP0029581 (hypocrellin A)

3D-SDF for NP0029581 (hypocrellin A)

PDB for NP0029581 (hypocrellin A)

3D PDB for NP0029581 (hypocrellin A)

SMILES for NP0029581 (hypocrellin A)

INCHI for NP0029581 (hypocrellin A)

Structure for NP0029581 (hypocrellin A)

3D Structure for NP0029581 (hypocrellin A)