NP-MRD: Showing NP-Card for [9,10a-dihydroxy-4a-({2-[(1-hydroxyethylidene)amino]-2-{[2,4,5-trihydroxy-6-(hydroxymethyl)oxan-3-yl]-c-hydroxycarbonimidoyl}ethyl}sulfanyl)-1-methyl-5,10-dioxo-octahydro-1h-naphtho[2,3-c]pyran-3-yl]acetic acid (NP0281084)

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Record Information

Version

2.0

Created at

2022-09-09 07:13:20 UTC

Updated at

2022-09-09 07:13:21 UTC

NP-MRD ID

NP0281084

Secondary Accession Numbers

None

Natural Product Identification

Common Name

[9,10a-dihydroxy-4a-({2-[(1-hydroxyethylidene)amino]-2-{[2,4,5-trihydroxy-6-(hydroxymethyl)oxan-3-yl]-c-hydroxycarbonimidoyl}ethyl}sulfanyl)-1-methyl-5,10-dioxo-octahydro-1h-naphtho[2,3-c]pyran-3-yl]acetic acid

Description

2-[9,10A-dihydroxy-4a-({2-[(1-hydroxyethylidene)amino]-2-{[2,4,5-trihydroxy-6-(hydroxymethyl)oxan-3-yl]-C-hydroxycarbonimidoyl}ethyl}sulfanyl)-1-methyl-5,10-dioxo-dodecahydro-1H-naphtho[2,3-c]pyran-3-yl]acetic acid belongs to the class of organic compounds known as naphthopyranones. Naphthopyranones are compounds containing a naphthopyran skeleton where a ring carbon bears a carboxylic acid group. Naphthtopyran is made up of the pyran ring fused to a naphthalene ring system. [9,10a-dihydroxy-4a-({2-[(1-hydroxyethylidene)amino]-2-{[2,4,5-trihydroxy-6-(hydroxymethyl)oxan-3-yl]-c-hydroxycarbonimidoyl}ethyl}sulfanyl)-1-methyl-5,10-dioxo-octahydro-1h-naphtho[2,3-c]pyran-3-yl]acetic acid is found in Streptomyces rosa. Based on a literature review very few articles have been published on 2-[9,10a-dihydroxy-4a-({2-[(1-hydroxyethylidene)amino]-2-{[2,4,5-trihydroxy-6-(hydroxymethyl)oxan-3-yl]-C-hydroxycarbonimidoyl}ethyl}sulfanyl)-1-methyl-5,10-dioxo-dodecahydro-1H-naphtho[2,3-c]pyran-3-yl]acetic acid.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309092209132D          

 44 47  0  0  0  0            999 V2000
    5.0013    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    4.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    3.3000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    1.6500    0.0000 S   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
    3.5724    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
    5.0013    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    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    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.8875    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.0000    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.4289    4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    5.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    4.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  2  0  0  0  0
  4  5  1  4  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
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  5 31  1  0  0  0  0
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 37 38  1  0  0  0  0
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 41 42  1  0  0  0  0
 41 43  1  0  0  0  0
 34 43  1  0  0  0  0
 43 44  1  0  0  0  0
M  END

     RDKit          3D

 84 87  0  0  0  0  0  0  0  0999 V2000
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    1.2929   -2.0257   -1.5801 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9992   -2.5080   -2.8903 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1343   -0.8179   -1.4014 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2279    0.1892   -0.4944 C   0  0  1  0  0  0  0  0  0  0  0  0
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   -2.6254   -0.2187   -0.3636 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.3146   -1.5074   -1.0149 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.7534    3.1202   -1.9607 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4995    2.1020   -0.8880 C   0  0  2  0  0  0  0  0  0  0  0  0
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    3.3579   -0.1434    0.4770 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.6831   -0.1802    0.3171 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.2857    0.9417   -0.5262 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.3001    2.1594    0.1235 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5530    0.5727   -0.8882 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4140    0.3883    0.1794 C   0  0  1  0  0  0  0  0  0  0  0  0
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 19 62  1  0
M  END


  Mrv1652309092209132D          

 44 47  0  0  0  0            999 V2000
    5.0013    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    4.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    3.3000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    1.6500    0.0000 S   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
    3.5724    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
    5.0013    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    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    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.8875    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    5.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    4.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  2  0  0  0  0
  4  5  1  4  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
 10 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
  8 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 23 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 22 28  1  0  0  0  0
 28 29  1  0  0  0  0
  8 29  1  0  0  0  0
 29 30  2  0  0  0  0
  5 31  1  0  0  0  0
 31 32  1  0  0  0  0
 31 33  2  0  0  0  0
 33 34  1  4  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 35 37  1  0  0  0  0
 37 38  1  0  0  0  0
 38 39  1  0  0  0  0
 39 40  1  0  0  0  0
 38 41  1  0  0  0  0
 41 42  1  0  0  0  0
 41 43  1  0  0  0  0
 34 43  1  0  0  0  0
 43 44  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0281084

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1OC(CC(O)=O)CC2(SCC(N=C(C)O)C(O)=NC3C(O)OC(CO)C(O)C3O)C(=O)C3CCCC(O)C3C(=O)C12O

> <INCHI_IDENTIFIER>
InChI=1S/C27H40N2O14S/c1-10-27(41)23(38)18-13(4-3-5-15(18)32)22(37)26(27,7-12(42-10)6-17(33)34)44-9-14(28-11(2)31)24(39)29-19-21(36)20(35)16(8-30)43-25(19)40/h10,12-16,18-21,25,30,32,35-36,40-41H,3-9H2,1-2H3,(H,28,31)(H,29,39)(H,33,34)

> <INCHI_KEY>
ABZXRWVSQAVBPT-UHFFFAOYSA-N

> <FORMULA>
C27H40N2O14S

> <MOLECULAR_WEIGHT>
648.68

> <EXACT_MASS>
648.22002515

> <JCHEM_ACCEPTOR_COUNT>
16

> <JCHEM_ATOM_COUNT>
84

> <JCHEM_AVERAGE_POLARIZABILITY>
64.4279730855397

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
9

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-[9,10a-dihydroxy-4a-({2-[(1-hydroxyethylidene)amino]-2-{[2,4,5-trihydroxy-6-(hydroxymethyl)oxan-3-yl]-C-hydroxycarbonimidoyl}ethyl}sulfanyl)-1-methyl-5,10-dioxo-dodecahydro-1H-naphtho[2,3-c]pyran-3-yl]acetic acid

> <JCHEM_LOGP>
-2.2901468703181864

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
4.03549757160594

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.262577988277916

> <JCHEM_PKA_STRONGEST_BASIC>
1.559139894805049

> <JCHEM_POLAR_SURFACE_AREA>
276.46

> <JCHEM_REFRACTIVITY>
148.0009

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
[9,10a-dihydroxy-4a-({2-[(1-hydroxyethylidene)amino]-2-{[2,4,5-trihydroxy-6-(hydroxymethyl)oxan-3-yl]-C-hydroxycarbonimidoyl}ethyl}sulfanyl)-1-methyl-5,10-dioxo-octahydro-1H-naphtho[2,3-c]pyran-3-yl]acetic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 09-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   09-SEP-22         0                                  
HETATM    1  C   UNK     0       9.336   8.470   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.002   7.700   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       6.668   8.470   0.000  0.00  0.00           O+0
HETATM    4  N   UNK     0       8.002   6.160   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0       6.668   5.390   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.668   3.850   0.000  0.00  0.00           C+0
HETATM    7  S   UNK     0       5.335   3.080   0.000  0.00  0.00           S+0
HETATM    8  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       9.336   2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      10.669   1.540   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      12.003   2.310   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0      10.669  -0.000   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0       8.002  -0.000   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       5.335  -1.540   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       4.001  -2.310   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      -0.000   0.000   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       4.001   3.850   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       5.335   6.160   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       5.335   7.700   0.000  0.00  0.00           O+0
HETATM   33  N   UNK     0       4.001   5.390   0.000  0.00  0.00           N+0
HETATM   34  C   UNK     0       2.667   6.160   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       1.334   5.390   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
HETATM   37  O   UNK     0      -0.000   6.160   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0      -0.000   7.700   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      -1.334   8.470   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0      -2.667   7.700   0.000  0.00  0.00           O+0
HETATM   41  C   UNK     0       1.334   8.470   0.000  0.00  0.00           C+0
HETATM   42  O   UNK     0       1.334  10.010   0.000  0.00  0.00           O+0
HETATM   43  C   UNK     0       2.667   7.700   0.000  0.00  0.00           C+0
HETATM   44  O   UNK     0       4.001   8.470   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6   31                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   18   29                                             
CONECT    9    8   10                                                       
CONECT   10    9   11   15                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12                                                            
CONECT   15   10   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16    8   19   20                                             
CONECT   19   18                                                            
CONECT   20   18   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23   28                                                  
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   22   29                                                  
CONECT   29   28    8   30                                                  
CONECT   30   29                                                            
CONECT   31    5   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31   34                                                       
CONECT   34   33   35   43                                                  
CONECT   35   34   36   37                                                  
CONECT   36   35                                                            
CONECT   37   35   38                                                       
CONECT   38   37   39   41                                                  
CONECT   39   38   40                                                       
CONECT   40   39                                                            
CONECT   41   38   42   43                                                  
CONECT   42   41                                                            
CONECT   43   41   34   44                                                  
CONECT   44   43                                                            
MASTER        0    0    0    0    0    0    0    0   44    0   94    0
END

View in JSmol

Synonyms

Value	Source
2-[9,10a-Dihydroxy-4a-({2-[(1-hydroxyethylidene)amino]-2-{[2,4,5-trihydroxy-6-(hydroxymethyl)oxan-3-yl]-C-hydroxycarbonimidoyl}ethyl}sulfanyl)-1-methyl-5,10-dioxo-dodecahydro-1H-naphtho[2,3-c]pyran-3-yl]acetate	Generator
2-[9,10a-Dihydroxy-4a-({2-[(1-hydroxyethylidene)amino]-2-{[2,4,5-trihydroxy-6-(hydroxymethyl)oxan-3-yl]-C-hydroxycarbonimidoyl}ethyl}sulphanyl)-1-methyl-5,10-dioxo-dodecahydro-1H-naphtho[2,3-c]pyran-3-yl]acetate	Generator
2-[9,10a-Dihydroxy-4a-({2-[(1-hydroxyethylidene)amino]-2-{[2,4,5-trihydroxy-6-(hydroxymethyl)oxan-3-yl]-C-hydroxycarbonimidoyl}ethyl}sulphanyl)-1-methyl-5,10-dioxo-dodecahydro-1H-naphtho[2,3-c]pyran-3-yl]acetic acid	Generator

Chemical Formula

C₂₇H₄₀N₂O₁₄S

Average Mass

648.6800 Da

Monoisotopic Mass

648.22003 Da

IUPAC Name

2-[9,10a-dihydroxy-4a-({2-[(1-hydroxyethylidene)amino]-2-{[2,4,5-trihydroxy-6-(hydroxymethyl)oxan-3-yl]-C-hydroxycarbonimidoyl}ethyl}sulfanyl)-1-methyl-5,10-dioxo-dodecahydro-1H-naphtho[2,3-c]pyran-3-yl]acetic acid

Traditional Name

[9,10a-dihydroxy-4a-({2-[(1-hydroxyethylidene)amino]-2-{[2,4,5-trihydroxy-6-(hydroxymethyl)oxan-3-yl]-C-hydroxycarbonimidoyl}ethyl}sulfanyl)-1-methyl-5,10-dioxo-octahydro-1H-naphtho[2,3-c]pyran-3-yl]acetic acid

CAS Registry Number

Not Available

SMILES

CC1OC(CC(O)=O)CC2(SCC(N=C(C)O)C(O)=NC3C(O)OC(CO)C(O)C3O)C(=O)C3CCCC(O)C3C(=O)C12O

InChI Identifier

InChI=1S/C27H40N2O14S/c1-10-27(41)23(38)18-13(4-3-5-15(18)32)22(37)26(27,7-12(42-10)6-17(33)34)44-9-14(28-11(2)31)24(39)29-19-21(36)20(35)16(8-30)43-25(19)40/h10,12-16,18-21,25,30,32,35-36,40-41H,3-9H2,1-2H3,(H,28,31)(H,29,39)(H,33,34)

InChI Key

ABZXRWVSQAVBPT-UHFFFAOYSA-N

Experimental Spectra

Not Available

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

Species Name	Source	Reference
Streptomyces rosa	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as naphthopyranones. Naphthopyranones are compounds containing a naphthopyran skeleton where a ring carbon bears a carboxylic acid group. Naphthtopyran is made up of the pyran ring fused to a naphthalene ring system.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Naphthopyrans

Sub Class

Naphthopyranones

Direct Parent

Naphthopyranones

Alternative Parents

Substituents

Naphthopyranone
N-acyl-alpha-hexosamine
Hexose monosaccharide
Naphthalene
Pyranone
Pyran
Oxane
Monosaccharide
Tertiary alcohol
Cyclic alcohol
Secondary alcohol
Ketone
Hemiacetal
Oxacycle
Dialkylthioether
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Sulfenyl compound
Thioether
Polyol
Monocarboxylic acid or derivatives
Ether
Dialkyl ether
Carboxylic acid
Carboxylic acid derivative
Carboximidic acid derivative
Carboximidic acid
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Primary alcohol
Organosulfur compound
Organooxygen compound
Organonitrogen compound
Carbonyl group
Alcohol
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic 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	-2.3	ChemAxon
pKa (Strongest Acidic)	3.26	ChemAxon
pKa (Strongest Basic)	1.56	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	16	ChemAxon
Hydrogen Donor Count	9	ChemAxon
Polar Surface Area	276.46 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	148 m³·mol⁻¹	ChemAxon
Polarizability	64.43 Å³	ChemAxon
Number of Rings	4	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

HMDB ID

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DrugBank ID

Not Available

Phenol Explorer Compound ID

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FoodDB ID

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KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

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Wikipedia Link

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METLIN ID

Not Available

PubChem Compound

163107034

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for [9,10a-dihydroxy-4a-({2-[(1-hydroxyethylidene)amino]-2-{[2,4,5-trihydroxy-6-(hydroxymethyl)oxan-3-yl]-c-hydroxycarbonimidoyl}ethyl}sulfanyl)-1-methyl-5,10-dioxo-octahydro-1h-naphtho[2,3-c]pyran-3-yl]acetic acid (NP0281084)

MOL for NP0281084 ([9,10a-dihydroxy-4a-({2-[(1-hydroxyethylidene)amino]-2-{[2,4,5-trihydroxy-6-(hydroxymethyl)oxan-3-yl]-c-hydroxycarbonimidoyl}ethyl}sulfanyl)-1-methyl-5,10-dioxo-octahydro-1h-naphtho[2,3-c]pyran-3-yl]acetic acid)

3D MOL for NP0281084 ([9,10a-dihydroxy-4a-({2-[(1-hydroxyethylidene)amino]-2-{[2,4,5-trihydroxy-6-(hydroxymethyl)oxan-3-yl]-c-hydroxycarbonimidoyl}ethyl}sulfanyl)-1-methyl-5,10-dioxo-octahydro-1h-naphtho[2,3-c]pyran-3-yl]acetic acid)

3D SDF for NP0281084 ([9,10a-dihydroxy-4a-({2-[(1-hydroxyethylidene)amino]-2-{[2,4,5-trihydroxy-6-(hydroxymethyl)oxan-3-yl]-c-hydroxycarbonimidoyl}ethyl}sulfanyl)-1-methyl-5,10-dioxo-octahydro-1h-naphtho[2,3-c]pyran-3-yl]acetic acid)

3D-SDF for NP0281084 ([9,10a-dihydroxy-4a-({2-[(1-hydroxyethylidene)amino]-2-{[2,4,5-trihydroxy-6-(hydroxymethyl)oxan-3-yl]-c-hydroxycarbonimidoyl}ethyl}sulfanyl)-1-methyl-5,10-dioxo-octahydro-1h-naphtho[2,3-c]pyran-3-yl]acetic acid)

PDB for NP0281084 ([9,10a-dihydroxy-4a-({2-[(1-hydroxyethylidene)amino]-2-{[2,4,5-trihydroxy-6-(hydroxymethyl)oxan-3-yl]-c-hydroxycarbonimidoyl}ethyl}sulfanyl)-1-methyl-5,10-dioxo-octahydro-1h-naphtho[2,3-c]pyran-3-yl]acetic acid)

3D PDB for NP0281084 ([9,10a-dihydroxy-4a-({2-[(1-hydroxyethylidene)amino]-2-{[2,4,5-trihydroxy-6-(hydroxymethyl)oxan-3-yl]-c-hydroxycarbonimidoyl}ethyl}sulfanyl)-1-methyl-5,10-dioxo-octahydro-1h-naphtho[2,3-c]pyran-3-yl]acetic acid)

SMILES for NP0281084 ([9,10a-dihydroxy-4a-({2-[(1-hydroxyethylidene)amino]-2-{[2,4,5-trihydroxy-6-(hydroxymethyl)oxan-3-yl]-c-hydroxycarbonimidoyl}ethyl}sulfanyl)-1-methyl-5,10-dioxo-octahydro-1h-naphtho[2,3-c]pyran-3-yl]acetic acid)

INCHI for NP0281084 ([9,10a-dihydroxy-4a-({2-[(1-hydroxyethylidene)amino]-2-{[2,4,5-trihydroxy-6-(hydroxymethyl)oxan-3-yl]-c-hydroxycarbonimidoyl}ethyl}sulfanyl)-1-methyl-5,10-dioxo-octahydro-1h-naphtho[2,3-c]pyran-3-yl]acetic acid)

Structure for NP0281084 ([9,10a-dihydroxy-4a-({2-[(1-hydroxyethylidene)amino]-2-{[2,4,5-trihydroxy-6-(hydroxymethyl)oxan-3-yl]-c-hydroxycarbonimidoyl}ethyl}sulfanyl)-1-methyl-5,10-dioxo-octahydro-1h-naphtho[2,3-c]pyran-3-yl]acetic acid)

3D Structure for NP0281084 ([9,10a-dihydroxy-4a-({2-[(1-hydroxyethylidene)amino]-2-{[2,4,5-trihydroxy-6-(hydroxymethyl)oxan-3-yl]-c-hydroxycarbonimidoyl}ethyl}sulfanyl)-1-methyl-5,10-dioxo-octahydro-1h-naphtho[2,3-c]pyran-3-yl]acetic acid)