NP-MRD: Showing NP-Card for Aranciamycin A (NP0331159)

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Record Information

Version

2.0

Created at

2022-11-17 19:07:31 UTC

Updated at

2024-09-03 04:14:46 UTC

NP-MRD ID

NP0331159

Natural Product DOI

https://doi.org/10.57994/0034

Secondary Accession Numbers

NP0308966

Natural Product Identification

Common Name

Aranciamycin A

Description

(8R,10S)-10-[(6-deoxy-2-O-methyl-alpha-L-mannopyranosyl)oxy]-7,8,9,10-tetrahydro-1,8,11-trihydroxy-8-methyl-5,12-naphthacenedione belongs to the class of organic compounds known as anthracyclines. These are polyketides containing a tetracenequinone ring structure with a sugar attached by glycosidic linkage. Based on a literature review very few articles have been published on (8R,10S)-10-[(6-deoxy-2-O-methyl-alpha-L-mannopyranosyl)oxy]-7,8,9,10-tetrahydro-1,8,11-trihydroxy-8-methyl-5,12-naphthacenedione.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309112205102D          

 36 40  0  0  1  0            999 V2000
    7.1447    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.7158   -1.6500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.0013   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.7158    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    0.8250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.5282    0.6817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9979    1.6002    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    4.2868   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    7.1447   -1.6500    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.8592   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
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  8  9  1  6  0  0  0
  8 10  1  1  0  0  0
  8 11  1  0  0  0  0
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 12 18  1  0  0  0  0
  6 18  1  0  0  0  0
 15 19  1  0  0  0  0
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 35 36  1  6  0  0  0
M  END

     RDKit          3D

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    0.4814   -1.1173    0.2783 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1596    1.4104    1.1695 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.2235   -2.7612   -1.9766 H   0  0  0  0  0  0  0  0  0  0  0  0
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 28 29  2  0
  4  3  1  0
 18  6  1  0
 27 21  1  0
 18 12  1  0
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  1 37  1  0
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M  END


  Mrv1652309112205102D          

 36 40  0  0  1  0            999 V2000
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    6.4302   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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  4 30  1  0  0  0  0
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 33 34  1  1  0  0  0
 33 35  1  0  0  0  0
  3 35  1  0  0  0  0
 35 36  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0331159

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CO[C@@H]1[C@H](O)[C@@H](O)[C@H](C)O[C@H]1O[C@H]1C[C@](C)(O)CC2=CC3=C(C(O)=C12)C(=O)C1=C(O)C=CC=C1C3=O

> <INCHI_IDENTIFIER>
InChI=1S/C26H28O10/c1-10-19(28)23(32)24(34-3)25(35-10)36-15-9-26(2,33)8-11-7-13-18(21(30)16(11)15)22(31)17-12(20(13)29)5-4-6-14(17)27/h4-7,10,15,19,23-25,27-28,30,32-33H,8-9H2,1-3H3/t10-,15-,19-,23+,24+,25-,26+/m0/s1

> <INCHI_KEY>
DEPMSUJGYKZLRC-ZCUANGBISA-N

> <FORMULA>
C26H28O10

> <MOLECULAR_WEIGHT>
500.5

> <EXACT_MASS>
500.168247102

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
64

> <JCHEM_AVERAGE_POLARIZABILITY>
50.575736234061026

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(8R,10S)-10-{[(2R,3R,4R,5R,6S)-4,5-dihydroxy-3-methoxy-6-methyloxan-2-yl]oxy}-1,8,11-trihydroxy-8-methyl-5,7,8,9,10,12-hexahydrotetracene-5,12-dione

> <JCHEM_LOGP>
2.573283530333332

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.3852592512253

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.6518682930174435

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8979419778602136

> <JCHEM_POLAR_SURFACE_AREA>
162.98000000000002

> <JCHEM_REFRACTIVITY>
125.9954

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(8R,10S)-10-{[(2R,3R,4R,5R,6S)-4,5-dihydroxy-3-methoxy-6-methyloxan-2-yl]oxy}-1,8,11-trihydroxy-8-methyl-9,10-dihydro-7H-tetracene-5,12-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 11-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-22         0                                  
HETATM    1  C   UNK     0      13.337   0.000   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      12.003  -0.770   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      12.003  -2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      10.669  -3.080   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       9.336  -2.310   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       9.336  -0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      10.669   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      10.669   1.540   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      12.186   1.273   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      11.196   2.987   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       9.336   2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       6.668  -2.310   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       8.002  -0.000   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       4.001  -2.310   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      -0.000   0.000   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       4.001   3.850   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0      10.669  -4.620   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      12.003  -5.390   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      12.003  -6.930   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      13.337  -4.620   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      14.670  -5.390   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0      13.337  -3.080   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0      14.670  -2.310   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   35                                                  
CONECT    4    3    5   30                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7   18                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   10   11                                             
CONECT    9    8                                                            
CONECT   10    8                                                            
CONECT   11    8   12                                                       
CONECT   12   11   13   18                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   28                                                  
CONECT   15   14   16   19                                                  
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   12    6                                                  
CONECT   19   15   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22   27                                                  
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   21   28                                                  
CONECT   28   27   14   29                                                  
CONECT   29   28                                                            
CONECT   30    4   31                                                       
CONECT   31   30   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33    3   36                                                  
CONECT   36   35                                                            
MASTER        0    0    0    0    0    0    0    0   36    0   80    0
END

View in JSmol

Synonyms

Value	Source
(8R,10S)-10-[(6-Deoxy-2-O-methyl-a-L-mannopyranosyl)oxy]-7,8,9,10-tetrahydro-1,8,11-trihydroxy-8-methyl-5,12-naphthacenedione	Generator
(8R,10S)-10-[(6-Deoxy-2-O-methyl-α-L-mannopyranosyl)oxy]-7,8,9,10-tetrahydro-1,8,11-trihydroxy-8-methyl-5,12-naphthacenedione	Generator

Chemical Formula

C₂₆H₂₈O₁₀

Average Mass

500.5000 Da

Monoisotopic Mass

500.16825 Da

IUPAC Name

(8R,10S)-10-{[(2R,3R,4R,5R,6S)-4,5-dihydroxy-3-methoxy-6-methyloxan-2-yl]oxy}-1,8,11-trihydroxy-8-methyl-5,7,8,9,10,12-hexahydrotetracene-5,12-dione

Traditional Name

(8R,10S)-10-{[(2R,3R,4R,5R,6S)-4,5-dihydroxy-3-methoxy-6-methyloxan-2-yl]oxy}-1,8,11-trihydroxy-8-methyl-9,10-dihydro-7H-tetracene-5,12-dione

CAS Registry Number

Not Available

SMILES

CO[C@@H]1[C@H](O)[C@@H](O)[C@H](C)O[C@H]1O[C@H]1C[C@](C)(O)CC2=CC3=C(C(O)=C12)C(=O)C1=C(O)C=CC=C1C3=O

InChI Identifier

InChI=1S/C26H28O10/c1-10-19(28)23(32)24(34-3)25(35-10)36-15-9-26(2,33)8-11-7-13-18(21(30)16(11)15)22(31)17-12(20(13)29)5-4-6-14(17)27/h4-7,10,15,19,23-25,27-28,30,32-33H,8-9H2,1-3H3/t10-,15-,19-,23+,24+,25-,26+/m0/s1

InChI Key

DEPMSUJGYKZLRC-ZCUANGBISA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CDCl3, experimental)	z.khalil@uq.edu.au	Not Available	Not Available	2022-11-17	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, C2D6OS, experimental)	z.khalil@uq.edu.au	Not Available	Not Available	2022-11-17	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, C2D6OS, experimental)	z.khalil@uq.edu.au	Not Available	Not Available	2022-11-17	View Spectrum
ROESY NMR	[¹H, ¹H] NMR Spectrum (2D, 600 MHz, CDCl3, experimental)	z.khalil@uq.edu.au	Not Available	Not Available	2022-11-17	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, CDCl3, experimental)	z.khalil@uq.edu.au	Not Available	Not Available	2022-11-17	View Spectrum
HMBC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, CDCl3, experimental)	z.khalil@uq.edu.au	Not Available	Not Available	2022-11-17	View Spectrum
COSY NMR	[¹H, ¹H] NMR Spectrum (2D, 600 MHz, CDCl3, experimental)	z.khalil@uq.edu.au	Not Available	Not Available	2022-11-17	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, C2D6OS, experimental)	z.khalil@uq.edu.au	Not Available	Not Available	2022-11-17	View Spectrum
ROESY NMR	[¹H, ¹H] NMR Spectrum (2D, 600 MHz, C2D6OS, experimental)	z.khalil@uq.edu.au	Not Available	Not Available	2022-11-17	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, C2D6OS, experimental)	z.khalil@uq.edu.au	Not Available	Not Available	2022-11-17	View Spectrum
HMBC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, C2D6OS, experimental)	z.khalil@uq.edu.au	Not Available	Not Available	2022-11-17	View Spectrum
COSY NMR	[¹H, ¹H] NMR Spectrum (2D, 600 MHz, C2D6OS, experimental)	z.khalil@uq.edu.au	Not Available	Not Available	2022-11-17	View Spectrum
HSQC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, C2D6OS, experimental)	z.khalil@uq.edu.au	Not Available	Not Available	2022-11-17	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, C2D6OS, experimental)	z.khalil@uq.edu.au	Not Available	Not Available	2022-11-17	View Spectrum
HSQC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, CDCl3, experimental)	z.khalil@uq.edu.au	Not Available	Not Available	2022-11-17	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CDCl3, experimental)	z.khalil@uq.edu.au	Not Available	Not Available	2022-11-17	View Spectrum

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as anthracyclines. These are polyketides containing a tetracenequinone ring structure with a sugar attached by glycosidic linkage.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Anthracyclines

Sub Class

Not Available

Direct Parent

Anthracyclines

Alternative Parents

Substituents

Anthracycline
Anthracyclinone-skeleton
Tetracenequinone
9,10-anthraquinone
1,4-anthraquinone
Anthracene
Hexose monosaccharide
Glycosyl compound
O-glycosyl compound
Tetralin
Aryl ketone
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Benzenoid
Monosaccharide
Oxane
Vinylogous acid
Tertiary alcohol
Secondary alcohol
Ketone
Acetal
Ether
Dialkyl ether
Organoheterocyclic compound
Oxacycle
Polyol
Alcohol
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Organooxygen compound
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	2.57	ChemAxon
pKa (Strongest Acidic)	7.65	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	162.98 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	126 m³·mol⁻¹	ChemAxon
Polarizability	50.58 Å³	ChemAxon
Number of Rings	5	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

34499563

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

122177932

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Aranciamycin A (NP0331159)

MOL for NP0331159 (Aranciamycin A)

3D MOL for NP0331159 (Aranciamycin A)

3D SDF for NP0331159 (Aranciamycin A)

3D-SDF for NP0331159 (Aranciamycin A)

PDB for NP0331159 (Aranciamycin A)

3D PDB for NP0331159 (Aranciamycin A)

SMILES for NP0331159 (Aranciamycin A)

INCHI for NP0331159 (Aranciamycin A)

Structure for NP0331159 (Aranciamycin A)

3D Structure for NP0331159 (Aranciamycin A)