NP-MRD: Showing NP-Card for Nanaomycin A (NP0004172)

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Record Information

Version

1.0

Created at

2020-12-09 01:40:10 UTC

Updated at

2021-07-15 16:48:27 UTC

NP-MRD ID

NP0004172

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Nanaomycin A

Provided By

NPAtlas

Description

2-[(1R,3S)-9-hydroxy-1-methyl-5,10-dioxo-1H,3H,4H,5H,10H-naphtho[2,3-c]pyran-3-yl]acetic acid is also known as DHK. Nanaomycin A is found in Streptomyces, Streptomyces coelicolor, Streptomyces rosa, Streptomyces rosa var. notoensis, Streptomyces roseofulvus and Streptomyces tanashiensis. It was first documented in 1975 (PMID: 1201970). Based on a literature review very few articles have been published on 2-[(1R,3S)-9-hydroxy-1-methyl-5,10-dioxo-1H,3H,4H,5H,10H-naphtho[2,3-c]pyran-3-yl]acetic acid.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242118043D          

 36 38  0  0  0  0            999 V2000
    1.1213   -2.3523   -1.8233 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1440   -1.8495   -0.3964 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3123   -1.1941   -0.1282 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5934   -0.1439   -0.9746 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.7312    0.6374   -0.3559 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.3966    1.1752    0.9879 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3626    0.4131    2.0069 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1097    2.5190    1.1928 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4431    0.7491   -1.2728 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1864    0.3460   -0.5845 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0266   -0.8895   -0.1587 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1991   -1.2827    0.5116 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2842   -2.4656    0.8883 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2482   -0.2974    0.7077 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4390   -0.6193    1.3414 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6537   -1.8742    1.7985 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4309    0.3712    1.5090 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2632    1.6500    1.0674 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0888    1.9780    0.4393 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1010    1.0200    0.2643 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8454    1.3493   -0.4014 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6904    2.5494   -0.8145 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1157   -2.8110   -2.0644 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9302   -1.5264   -2.5366 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3142   -3.0945   -1.9895 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0642   -2.7202    0.2788 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9734   -0.5672   -1.9263 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6307   -0.0090   -0.2193 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0192    1.5086   -0.9822 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3673    2.8617    1.7766 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6554    1.7987   -0.9146 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2439    0.8426   -2.3586 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1909   -2.7161    1.8302 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3292    0.0563    2.0081 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0633    2.3925    1.2207 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9140    2.9819    0.0724 H   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
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  4  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  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
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 15 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 11  2  1  0  0  0  0
 20 14  1  0  0  0  0
 21 10  1  0  0  0  0
  1 23  1  0  0  0  0
  1 24  1  0  0  0  0
  1 25  1  0  0  0  0
  2 26  1  1  0  0  0
  4 27  1  6  0  0  0
  5 28  1  0  0  0  0
  5 29  1  0  0  0  0
  8 30  1  0  0  0  0
  9 31  1  0  0  0  0
  9 32  1  0  0  0  0
 16 33  1  0  0  0  0
 17 34  1  0  0  0  0
 18 35  1  0  0  0  0
 19 36  1  0  0  0  0
M  END

     RDKit          3D

 36 38  0  0  0  0  0  0  0  0999 V2000
    1.1213   -2.3523   -1.8233 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1440   -1.8495   -0.3964 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3123   -1.1941   -0.1282 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5934   -0.1439   -0.9746 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.7312    0.6374   -0.3559 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3966    1.1752    0.9879 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3626    0.4131    2.0069 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1097    2.5190    1.1928 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4431    0.7491   -1.2728 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1864    0.3460   -0.5845 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0266   -0.8895   -0.1587 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1991   -1.2827    0.5116 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2842   -2.4656    0.8883 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2482   -0.2974    0.7077 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4390   -0.6193    1.3414 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6537   -1.8742    1.7985 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4309    0.3712    1.5090 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2632    1.6500    1.0674 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0888    1.9780    0.4393 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1010    1.0200    0.2643 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8454    1.3493   -0.4014 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6904    2.5494   -0.8145 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1157   -2.8110   -2.0644 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9302   -1.5264   -2.5366 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3142   -3.0945   -1.9895 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0642   -2.7202    0.2788 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9734   -0.5672   -1.9263 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6307   -0.0090   -0.2193 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0192    1.5086   -0.9822 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3673    2.8617    1.7766 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6554    1.7987   -0.9146 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2439    0.8426   -2.3586 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1909   -2.7161    1.8302 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3292    0.0563    2.0081 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0633    2.3925    1.2207 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9140    2.9819    0.0724 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  4  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  2  0
 15 16  1  0
 15 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 11  2  1  0
 20 14  1  0
 21 10  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  2 26  1  1
  4 27  1  6
  5 28  1  0
  5 29  1  0
  8 30  1  0
  9 31  1  0
  9 32  1  0
 16 33  1  0
 17 34  1  0
 18 35  1  0
 19 36  1  0
M  END


  Mrv1652306242118043D          

 36 38  0  0  0  0            999 V2000
    1.1213   -2.3523   -1.8233 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1440   -1.8495   -0.3964 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3123   -1.1941   -0.1282 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5934   -0.1439   -0.9746 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.7312    0.6374   -0.3559 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.3966    1.1752    0.9879 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3626    0.4131    2.0069 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1097    2.5190    1.1928 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4431    0.7491   -1.2728 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1864    0.3460   -0.5845 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0266   -0.8895   -0.1587 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1991   -1.2827    0.5116 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2842   -2.4656    0.8883 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2482   -0.2974    0.7077 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4390   -0.6193    1.3414 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6537   -1.8742    1.7985 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4309    0.3712    1.5090 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2632    1.6500    1.0674 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0888    1.9780    0.4393 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1010    1.0200    0.2643 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8454    1.3493   -0.4014 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6904    2.5494   -0.8145 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1157   -2.8110   -2.0644 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9302   -1.5264   -2.5366 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3142   -3.0945   -1.9895 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0642   -2.7202    0.2788 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9734   -0.5672   -1.9263 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6307   -0.0090   -0.2193 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0192    1.5086   -0.9822 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3673    2.8617    1.7766 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6554    1.7987   -0.9146 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2439    0.8426   -2.3586 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1909   -2.7161    1.8302 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3292    0.0563    2.0081 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0633    2.3925    1.2207 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9140    2.9819    0.0724 H   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
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  4  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  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
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 15 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 11  2  1  0  0  0  0
 20 14  1  0  0  0  0
 21 10  1  0  0  0  0
  1 23  1  0  0  0  0
  1 24  1  0  0  0  0
  1 25  1  0  0  0  0
  2 26  1  1  0  0  0
  4 27  1  6  0  0  0
  5 28  1  0  0  0  0
  5 29  1  0  0  0  0
  8 30  1  0  0  0  0
  9 31  1  0  0  0  0
  9 32  1  0  0  0  0
 16 33  1  0  0  0  0
 17 34  1  0  0  0  0
 18 35  1  0  0  0  0
 19 36  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0004172

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC(=O)C([H])([H])[C@@]1([H])O[C@@]([H])(C2=C(C(=O)C3=C([H])C([H])=C([H])C(O[H])=C3C2=O)C1([H])[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C16H14O6/c1-7-13-10(5-8(22-7)6-12(18)19)15(20)9-3-2-4-11(17)14(9)16(13)21/h2-4,7-8,17H,5-6H2,1H3,(H,18,19)/t7-,8+/m1/s1

> <INCHI_KEY>
ZCJHPTKRISJQTN-SFYZADRCSA-N

> <FORMULA>
C16H14O6

> <MOLECULAR_WEIGHT>
302.282

> <EXACT_MASS>
302.079038171

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
36

> <JCHEM_AVERAGE_POLARIZABILITY>
29.13614430463291

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-[(1R,3S)-9-hydroxy-1-methyl-5,10-dioxo-1H,3H,4H,5H,10H-naphtho[2,3-c]pyran-3-yl]acetic acid

> <ALOGPS_LOGP>
1.87

> <JCHEM_LOGP>
1.712014211

> <ALOGPS_LOGS>
-2.72

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
8.22585303658231

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.4849699991618888

> <JCHEM_PKA_STRONGEST_BASIC>
-4.20279829222987

> <JCHEM_POLAR_SURFACE_AREA>
100.9

> <JCHEM_REFRACTIVITY>
76.5456

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.78e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
dihydrokalafungin

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 36 38  0  0  0  0  0  0  0  0999 V2000
    1.1213   -2.3523   -1.8233 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1440   -1.8495   -0.3964 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3123   -1.1941   -0.1282 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5934   -0.1439   -0.9746 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.7312    0.6374   -0.3559 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3966    1.1752    0.9879 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3626    0.4131    2.0069 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1097    2.5190    1.1928 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4431    0.7491   -1.2728 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1864    0.3460   -0.5845 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0266   -0.8895   -0.1587 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1991   -1.2827    0.5116 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2842   -2.4656    0.8883 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2482   -0.2974    0.7077 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4390   -0.6193    1.3414 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6537   -1.8742    1.7985 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4309    0.3712    1.5090 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2632    1.6500    1.0674 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0888    1.9780    0.4393 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1010    1.0200    0.2643 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8454    1.3493   -0.4014 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6904    2.5494   -0.8145 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1157   -2.8110   -2.0644 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9302   -1.5264   -2.5366 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3142   -3.0945   -1.9895 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0642   -2.7202    0.2788 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9734   -0.5672   -1.9263 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6307   -0.0090   -0.2193 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0192    1.5086   -0.9822 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3673    2.8617    1.7766 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6554    1.7987   -0.9146 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2439    0.8426   -2.3586 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1909   -2.7161    1.8302 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3292    0.0563    2.0081 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0633    2.3925    1.2207 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9140    2.9819    0.0724 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  4  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  2  0
 15 16  1  0
 15 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 11  2  1  0
 20 14  1  0
 21 10  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  2 26  1  1
  4 27  1  6
  5 28  1  0
  5 29  1  0
  8 30  1  0
  9 31  1  0
  9 32  1  0
 16 33  1  0
 17 34  1  0
 18 35  1  0
 19 36  1  0
M  END

HEADER    PROTEIN                                 24-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-JUN-21         0                                  
HETATM    1  C   UNK     0       1.121  -2.352  -1.823  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.144  -1.849  -0.396  0.00  0.00           C+0
HETATM    3  O   UNK     0       2.312  -1.194  -0.128  0.00  0.00           O+0
HETATM    4  C   UNK     0       2.593  -0.144  -0.975  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.731   0.637  -0.356  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.397   1.175   0.988  0.00  0.00           C+0
HETATM    7  O   UNK     0       3.363   0.413   2.007  0.00  0.00           O+0
HETATM    8  O   UNK     0       3.110   2.519   1.193  0.00  0.00           O+0
HETATM    9  C   UNK     0       1.443   0.749  -1.273  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.186   0.346  -0.585  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.027  -0.890  -0.159  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.199  -1.283   0.512  0.00  0.00           C+0
HETATM   13  O   UNK     0      -1.284  -2.466   0.888  0.00  0.00           O+0
HETATM   14  C   UNK     0      -2.248  -0.297   0.708  0.00  0.00           C+0
HETATM   15  C   UNK     0      -3.439  -0.619   1.341  0.00  0.00           C+0
HETATM   16  O   UNK     0      -3.654  -1.874   1.799  0.00  0.00           O+0
HETATM   17  C   UNK     0      -4.431   0.371   1.509  0.00  0.00           C+0
HETATM   18  C   UNK     0      -4.263   1.650   1.067  0.00  0.00           C+0
HETATM   19  C   UNK     0      -3.089   1.978   0.439  0.00  0.00           C+0
HETATM   20  C   UNK     0      -2.101   1.020   0.264  0.00  0.00           C+0
HETATM   21  C   UNK     0      -0.845   1.349  -0.401  0.00  0.00           C+0
HETATM   22  O   UNK     0      -0.690   2.549  -0.815  0.00  0.00           O+0
HETATM   23  H   UNK     0       2.116  -2.811  -2.064  0.00  0.00           H+0
HETATM   24  H   UNK     0       0.930  -1.526  -2.537  0.00  0.00           H+0
HETATM   25  H   UNK     0       0.314  -3.095  -1.990  0.00  0.00           H+0
HETATM   26  H   UNK     0       1.064  -2.720   0.279  0.00  0.00           H+0
HETATM   27  H   UNK     0       2.973  -0.567  -1.926  0.00  0.00           H+0
HETATM   28  H   UNK     0       4.631  -0.009  -0.219  0.00  0.00           H+0
HETATM   29  H   UNK     0       4.019   1.509  -0.982  0.00  0.00           H+0
HETATM   30  H   UNK     0       2.367   2.862   1.777  0.00  0.00           H+0
HETATM   31  H   UNK     0       1.655   1.799  -0.915  0.00  0.00           H+0
HETATM   32  H   UNK     0       1.244   0.843  -2.359  0.00  0.00           H+0
HETATM   33  H   UNK     0      -3.191  -2.716   1.830  0.00  0.00           H+0
HETATM   34  H   UNK     0      -5.329   0.056   2.008  0.00  0.00           H+0
HETATM   35  H   UNK     0      -5.063   2.393   1.221  0.00  0.00           H+0
HETATM   36  H   UNK     0      -2.914   2.982   0.072  0.00  0.00           H+0
CONECT    1    2   23   24   25                                             
CONECT    2    1    3   11   26                                             
CONECT    3    2    4                                                       
CONECT    4    3    5    9   27                                             
CONECT    5    4    6   28   29                                             
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6   30                                                       
CONECT    9    4   10   31   32                                             
CONECT   10    9   11   21                                                  
CONECT   11   10   12    2                                                  
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15   20                                                  
CONECT   15   14   16   17                                                  
CONECT   16   15   33                                                       
CONECT   17   15   18   34                                                  
CONECT   18   17   19   35                                                  
CONECT   19   18   20   36                                                  
CONECT   20   19   21   14                                                  
CONECT   21   20   22   10                                                  
CONECT   22   21                                                            
CONECT   23    1                                                            
CONECT   24    1                                                            
CONECT   25    1                                                            
CONECT   26    2                                                            
CONECT   27    4                                                            
CONECT   28    5                                                            
CONECT   29    5                                                            
CONECT   30    8                                                            
CONECT   31    9                                                            
CONECT   32    9                                                            
CONECT   33   16                                                            
CONECT   34   17                                                            
CONECT   35   18                                                            
CONECT   36   19                                                            
MASTER        0    0    0    0    0    0    0    0   36    0   76    0
END

RDKit          3D

36 38  0  0  0  0  0  0  0  0999 V2000
    1.1213   -2.3523   -1.8233 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1440   -1.8495   -0.3964 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3123   -1.1941   -0.1282 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5934   -0.1439   -0.9746 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.7312    0.6374   -0.3559 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3966    1.1752    0.9879 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3626    0.4131    2.0069 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1097    2.5190    1.1928 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4431    0.7491   -1.2728 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1864    0.3460   -0.5845 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0266   -0.8895   -0.1587 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1991   -1.2827    0.5116 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2842   -2.4656    0.8883 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2482   -0.2974    0.7077 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4390   -0.6193    1.3414 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6537   -1.8742    1.7985 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4309    0.3712    1.5090 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2632    1.6500    1.0674 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0888    1.9780    0.4393 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1010    1.0200    0.2643 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8454    1.3493   -0.4014 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6904    2.5494   -0.8145 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1157   -2.8110   -2.0644 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9302   -1.5264   -2.5366 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3142   -3.0945   -1.9895 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0642   -2.7202    0.2788 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9734   -0.5672   -1.9263 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6307   -0.0090   -0.2193 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0192    1.5086   -0.9822 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3673    2.8617    1.7766 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6554    1.7987   -0.9146 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2439    0.8426   -2.3586 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1909   -2.7161    1.8302 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3292    0.0563    2.0081 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0633    2.3925    1.2207 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9140    2.9819    0.0724 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  4  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  2  0
 15 16  1  0
 15 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 11  2  1  0
 20 14  1  0
 21 10  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  2 26  1  1
  4 27  1  6
  5 28  1  0
  5 29  1  0
  8 30  1  0
  9 31  1  0
  9 32  1  0
 16 33  1  0
 17 34  1  0
 18 35  1  0
 19 36  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Value	Source
DHK	Kegg
2-[(1R,3S)-9-Hydroxy-1-methyl-5,10-dioxo-1H,3H,4H,5H,10H-naphtho[2,3-c]pyran-3-yl]acetate	Generator
Nanaomycin a	MeSH

Chemical Formula

C₁₆H₁₄O₆

Average Mass

302.2820 Da

Monoisotopic Mass

302.07904 Da

IUPAC Name

2-[(1R,3S)-9-hydroxy-1-methyl-5,10-dioxo-1H,3H,4H,5H,10H-naphtho[2,3-c]pyran-3-yl]acetic acid

Traditional Name

dihydrokalafungin

CAS Registry Number

Not Available

SMILES

C[C@H]1O[C@H](CC(O)=O)CC2=C1C(=O)C1=C(C=CC=C1O)C2=O

InChI Identifier

InChI=1S/C16H14O6/c1-7-13-10(5-8(22-7)6-12(18)19)15(20)9-3-2-4-11(17)14(9)16(13)21/h2-4,7-8,17H,5-6H2,1H3,(H,18,19)/t7-,8+/m1/s1

InChI Key

ZCJHPTKRISJQTN-SFYZADRCSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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	NPAtlas	1201970
Streptomyces coelicolor	LOTUS Database	35616633
Streptomyces rosa	LOTUS Database	35616633
Streptomyces rosa var. notoensis	Bacteria	KNApSAcK
Streptomyces roseofulvus	LOTUS Database	35616633
Streptomyces tanashiensis	LOTUS Database	35616633

Chemical Taxonomy

Description

This compound belongs to the class of organic compounds known as benzoisochromanequinones. These are benzo derivatives of isochromanequinones. Isochromanequinones are structurally characterized by a quinone fused to an isochromane, and forming a naphtho[2,3-c]pyran-6,9-dione skeleton.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Isochromanequinones

Sub Class

Benzoisochromanequinones

Direct Parent

Benzoisochromanequinones

Alternative Parents

Substituents

Benzoisochromanequinone
Naphthopyranone
Naphthopyran
Naphthoquinone
Naphthalene
Aryl ketone
Quinone
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Pyranone
Benzenoid
Pyran
Vinylogous acid
Ketone
Carboxylic acid derivative
Carboxylic acid
Dialkyl ether
Ether
Monocarboxylic acid or derivatives
Oxacycle
Organoheterocyclic compound
Organic oxide
Organic oxygen compound
Hydrocarbon derivative
Carbonyl group
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

benzoisochromanequinone (CHEBI:31491 )

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	1.87	ALOGPS
logP	1.71	ChemAxon
logS	-2.7	ALOGPS
pKa (Strongest Acidic)	3.48	ChemAxon
pKa (Strongest Basic)	-4.2	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	100.9 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	76.55 m³·mol⁻¹	ChemAxon
Polarizability	29.14 Å³	ChemAxon
Number of Rings	3	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

NPAtlas ID

NPA013837

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

391930

KEGG Compound ID

C12436

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

443835

PDB ID

Not Available

ChEBI ID

31491

Good Scents ID

Not Available

References

General References

Tanaka H, Koyama Y, Nagai T, Marumo H, Omura S: Nanomycins, new antibiotics produced by a strain of Streptomyces. II. Structure and biosynthesis. J Antibiot (Tokyo). 1975 Nov;28(11):868-75. doi: 10.7164/antibiotics.28.868. [PubMed:1201970 ]

Showing NP-Card for Nanaomycin A (NP0004172)

MOL for NP0004172 (Nanaomycin A)

3D MOL for NP0004172 (Nanaomycin A)

3D SDF for NP0004172 (Nanaomycin A)

3D-SDF for NP0004172 (Nanaomycin A)

PDB for NP0004172 (Nanaomycin A)

3D PDB for NP0004172 (Nanaomycin A)

SMILES for NP0004172 (Nanaomycin A)

INCHI for NP0004172 (Nanaomycin A)

Structure for NP0004172 (Nanaomycin A)

3D Structure for NP0004172 (Nanaomycin A)