NP-MRD: Showing NP-Card for NSC 138425 (NP0062298)

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Record Information

Version

2.0

Created at

2022-04-28 06:59:19 UTC

Updated at

2022-04-28 06:59:19 UTC

NP-MRD ID

NP0062298

Secondary Accession Numbers

None

Natural Product Identification

Common Name

NSC 138425

Description

Kinamycin C belongs to the class of organic compounds known as naphthalenes. Naphthalenes are compounds containing a naphthalene moiety, which consists of two fused benzene rings. NSC 138425 is found in Streptomyces murayamaensis. NSC 138425 was first documented in 2006 (PMID: 17105273). Based on a literature review a small amount of articles have been published on kinamycin C (PMID: 28956437) (PMID: 24848236) (PMID: 16926632).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282208592D          

 36 39  0  0  1  0            999 V2000
    3.4623    2.3118    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2997    1.5030    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9189    0.9577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7562    0.1489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9745   -0.1146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8119   -0.9235    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3553    0.4306    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5180    1.2394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7990    1.6440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7037    2.4635    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    1.6084    3.2830    0.0000 N   0  5  0  0  0  0  0  0  0  0  0  0
    1.1920    1.0852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5359    0.3353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0583   -0.3374    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2369   -0.2602    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1069    0.4897    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3706    1.1624    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0268    1.9124    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7946    1.9895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2721    1.3168    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1385    2.7395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8684    0.1722    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7959    0.9435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2406   -0.9330    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0620   -0.8558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5395   -1.5285    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4058   -0.1059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4022   -1.0874    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9246   -1.7601    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1032   -1.6829    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2685   -2.5100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3754   -0.3963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1571   -0.1327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3198    0.6761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7006    1.2213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8632    2.0301    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  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  2  0  0  0  0
  5  7  1  0  0  0  0
  7  8  2  0  0  0  0
  2  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  2  0  0  0  0
  9 12  1  0  0  0  0
 12 13  2  0  0  0  0
  7 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 12 17  1  0  0  0  0
 17 18  1  6  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
 16 22  1  6  0  0  0
 16 23  1  1  0  0  0
 15 24  1  1  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 25 27  1  0  0  0  0
 14 28  1  6  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 29 31  1  0  0  0  0
  4 32  2  0  0  0  0
 32 33  1  0  0  0  0
 33 34  2  0  0  0  0
 34 35  1  0  0  0  0
  3 35  2  0  0  0  0
 35 36  1  0  0  0  0
M  CHG  2  10   1  11  -1
M  END

     RDKit          3D

 56 59  0  0  0  0  0  0  0  0999 V2000
   -1.3738   -4.6328    0.8035 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5235   -3.1887    1.0752 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0724   -2.7608    2.1195 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0457   -2.2521    0.1536 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1510   -0.8933    0.3413 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1074   -0.1238    0.3942 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0462    1.2590    0.4756 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2187    1.7987    0.5140 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4691    3.0370    0.5893 N   0  0  0  0  0  4  0  0  0  0  0  0
    1.7303    4.1136    1.1257 N   0  0  0  0  0  2  0  0  0  0  0  0
    2.1321    0.7707    0.4573 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5295    0.8412    0.4671 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0906    1.9728    0.5373 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2696   -0.3097    0.4008 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6395   -0.2706    0.4084 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4076    0.8327    0.4776 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2924   -1.5126    0.3361 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5970   -2.7045    0.2617 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2314   -2.6891    0.2574 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5538   -1.4954    0.3267 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1769   -1.5510    0.3179 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5507   -2.6382    0.2499 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4610   -0.3611    0.3867 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3825    1.8944    0.5049 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3064    3.1905   -0.0395 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5198    4.3454    0.6698 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4069    5.6475   -0.0317 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8036    4.2655    1.8893 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4483    1.1524   -0.2176 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.6633    1.0799    0.6866 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8793    1.8620   -1.3639 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0029   -0.1908   -0.6976 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.0306   -0.9838   -1.1954 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1324   -1.4290   -2.4999 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3033   -2.2700   -2.8527 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2468   -1.1055   -3.3028 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1248   -5.2522    1.3331 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4451   -4.8534   -0.2986 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3705   -4.9852    1.1650 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6627   -0.7288    1.3367 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2057    1.7758    0.5336 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3767   -1.5027    0.3408 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1439   -3.6306    0.2081 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6832   -3.6202    0.1993 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6388    2.0423    1.5955 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1770    6.3731    0.3134 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3745    6.0522    0.0808 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5953    5.4899   -1.1135 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8049    2.1081    1.0952 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5980    0.8658    0.1009 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5294    0.4117    1.5401 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1082    2.2043   -1.8803 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2989   -0.0000   -1.5632 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2430   -1.6690   -2.8964 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1375   -2.6293   -3.9079 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4198   -3.1520   -2.2090 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5 32  1  0
 32 33  1  0
 33 34  1  0
 34 35  1  0
 34 36  2  0
 32 29  1  0
 29 30  1  0
 29 31  1  6
 29 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 26 28  2  0
 24  7  1  0
  7  6  2  0
  6 23  1  0
 23 11  2  0
 11  8  1  0
  8  9  2  0
  9 10  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
  6  5  1  0
 21 23  1  0
  8  7  1  0
 20 14  1  0
  1 37  1  0
  1 38  1  0
  1 39  1  0
  5 40  1  1
 32 53  1  6
 35 54  1  0
 35 55  1  0
 35 56  1  0
 30 49  1  0
 30 50  1  0
 30 51  1  0
 31 52  1  0
 24 45  1  1
 27 46  1  0
 27 47  1  0
 27 48  1  0
 16 41  1  0
 17 42  1  0
 18 43  1  0
 19 44  1  0
M  CHG  2   9   1  10  -1
M  END


  Mrv1652304282208592D          

 36 39  0  0  1  0            999 V2000
    3.4623    2.3118    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2997    1.5030    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9189    0.9577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7562    0.1489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9745   -0.1146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8119   -0.9235    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3553    0.4306    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5180    1.2394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7990    1.6440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7037    2.4635    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    1.6084    3.2830    0.0000 N   0  5  0  0  0  0  0  0  0  0  0  0
    1.1920    1.0852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5359    0.3353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0583   -0.3374    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2369   -0.2602    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1069    0.4897    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3706    1.1624    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0268    1.9124    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7946    1.9895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2721    1.3168    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1385    2.7395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8684    0.1722    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7959    0.9435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2406   -0.9330    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0620   -0.8558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5395   -1.5285    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4058   -0.1059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4022   -1.0874    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9246   -1.7601    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1032   -1.6829    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2685   -2.5100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3754   -0.3963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1571   -0.1327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3198    0.6761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7006    1.2213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8632    2.0301    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  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  2  0  0  0  0
  5  7  1  0  0  0  0
  7  8  2  0  0  0  0
  2  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  2  0  0  0  0
  9 12  1  0  0  0  0
 12 13  2  0  0  0  0
  7 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 12 17  1  0  0  0  0
 17 18  1  6  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
 16 22  1  6  0  0  0
 16 23  1  1  0  0  0
 15 24  1  1  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 25 27  1  0  0  0  0
 14 28  1  6  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 29 31  1  0  0  0  0
  4 32  2  0  0  0  0
 32 33  1  0  0  0  0
 33 34  2  0  0  0  0
 34 35  1  0  0  0  0
  3 35  2  0  0  0  0
 35 36  1  0  0  0  0
M  CHG  2  10   1  11  -1
M  END
> <DATABASE_ID>
NP0062298

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@](C)(O)[C@H](OC(C)=O)C2=C1C1=C(C2=[N+]=[N-])C(=O)C2=C(O)C=CC=C2C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C24H20N2O10/c1-8(27)34-21-15-14-16(20(32)13-11(19(14)31)6-5-7-12(13)30)18(26-25)17(15)22(35-9(2)28)24(4,33)23(21)36-10(3)29/h5-7,21-23,30,33H,1-4H3/t21-,22+,23+,24+/m0/s1

> <INCHI_KEY>
MXDLFLPONIABIS-OLKYXYMISA-N

> <FORMULA>
C24H20N2O10

> <MOLECULAR_WEIGHT>
496.428

> <EXACT_MASS>
496.111794852

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
56

> <JCHEM_AVERAGE_POLARIZABILITY>
47.87423777290918

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,2R,3R,4S)-1,3-bis(acetyloxy)-2,9-dihydroxy-11-(-lambda5-diazynylidene)-2-methyl-5,10-dioxo-1H,2H,3H,4H,5H,10H,11H-benzo[b]fluoren-4-yl acetate

> <ALOGPS_LOGP>
2.32

> <JCHEM_LOGP>
-1.1964424742092785

> <ALOGPS_LOGS>
-3.65

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
8.991889430660866

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.059619319429814

> <JCHEM_PKA_STRONGEST_BASIC>
-3.7317223949752973

> <JCHEM_POLAR_SURFACE_AREA>
170.56999999999996

> <JCHEM_REFRACTIVITY>
117.74119999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.12e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2R,3R,4S)-1,3-bis(acetyloxy)-2,9-dihydroxy-11-(-lambda5-diazynylidene)-2-methyl-5,10-dioxo-1H,3H,4H-benzo[b]fluoren-4-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  O   UNK     0       6.463   4.315   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       6.159   2.806   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.315   1.788   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.012   0.278   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.552  -0.214   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       5.249  -1.724   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       4.397   0.804   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.700   2.314   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.358   3.069   0.000  0.00  0.00           C+0
HETATM   10  N   UNK     0       3.180   4.599   0.000  0.00  0.00           N+1
HETATM   11  N   UNK     0       3.002   6.128   0.000  0.00  0.00           N-1
HETATM   12  C   UNK     0       2.225   2.026   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.867   0.626   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.976  -0.630   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.442  -0.486   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -0.200   0.914   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.692   2.170   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       0.050   3.570   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      -1.483   3.714   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      -2.375   2.458   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      -2.125   5.114   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      -1.621   0.321   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      -1.486   1.761   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      -0.449  -1.742   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      -1.982  -1.598   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      -2.874  -2.853   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      -2.624  -0.198   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       2.617  -2.030   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       1.726  -3.286   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       0.193  -3.141   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       2.368  -4.685   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       8.167  -0.740   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       9.627  -0.248   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       9.930   1.262   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       8.774   2.280   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0       9.078   3.790   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    8                                                  
CONECT    3    2    4   35                                                  
CONECT    4    3    5   32                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8   13                                                  
CONECT    8    7    2    9                                                  
CONECT    9    8   10   12                                                  
CONECT   10    9   11                                                       
CONECT   11   10                                                            
CONECT   12    9   13   17                                                  
CONECT   13   12    7   14                                                  
CONECT   14   13   15   28                                                  
CONECT   15   14   16   24                                                  
CONECT   16   15   17   22   23                                             
CONECT   17   16   12   18                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19                                                            
CONECT   22   16                                                            
CONECT   23   16                                                            
CONECT   24   15   25                                                       
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25                                                            
CONECT   28   14   29                                                       
CONECT   29   28   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29                                                            
CONECT   32    4   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33   35                                                       
CONECT   35   34    3   36                                                  
CONECT   36   35                                                            
MASTER        0    0    0    0    0    0    0    0   36    0   78    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₄H₂₀N₂O₁₀

Average Mass

496.4280 Da

Monoisotopic Mass

496.11179 Da

IUPAC Name

(1R,2R,3R,4S)-1,3-bis(acetyloxy)-2,9-dihydroxy-11-(-lambda5-diazynylidene)-2-methyl-5,10-dioxo-1H,2H,3H,4H,5H,10H,11H-benzo[b]fluoren-4-yl acetate

Traditional Name

(1R,2R,3R,4S)-1,3-bis(acetyloxy)-2,9-dihydroxy-11-(-lambda5-diazynylidene)-2-methyl-5,10-dioxo-1H,3H,4H-benzo[b]fluoren-4-yl acetate

CAS Registry Number

Not Available

SMILES

CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@](C)(O)[C@H](OC(C)=O)C2=C1C1=C(C2=[N+]=[N-])C(=O)C2=C(O)C=CC=C2C1=O

InChI Identifier

InChI=1S/C24H20N2O10/c1-8(27)34-21-15-14-16(20(32)13-11(19(14)31)6-5-7-12(13)30)18(26-25)17(15)22(35-9(2)28)24(4,33)23(21)36-10(3)29/h5-7,21-23,30,33H,1-4H3/t21-,22+,23+,24+/m0/s1

InChI Key

MXDLFLPONIABIS-OLKYXYMISA-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 murayamaensis	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as naphthalenes. Naphthalenes are compounds containing a naphthalene moiety, which consists of two fused benzene rings.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Naphthalenes

Sub Class

Not Available

Direct Parent

Naphthalenes

Alternative Parents

Substituents

Naphthalene
Indene
Tricarboxylic acid or derivatives
Aryl ketone
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Vinylogous acid
Tertiary alcohol
Carboxylic acid ester
Diazo compound
Ketone
Organic diazonium salt
Carboxylic acid derivative
Organic oxygen compound
Organooxygen compound
Organic nitrogen compound
Organic zwitterion
Alcohol
Organic salt
Hydrocarbon derivative
Carbonyl group
Organic oxide
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic compounds

External Descriptors

kinamycin (CHEBI:48211 )

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	2.32	ALOGPS
logP	-1.2	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Acidic)	8.06	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	170.57 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	117.74 m³·mol⁻¹	ChemAxon
Polarizability	47.87 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00018812

Chemspider ID

23106969

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

135430800

PDB ID

Not Available

ChEBI ID

48211

Good Scents ID

Not Available

References

General References

Herzon SB: The Mechanism of Action of (-)-Lomaiviticin A. Acc Chem Res. 2017 Oct 17;50(10):2577-2588. doi: 10.1021/acs.accounts.7b00347. Epub 2017 Sep 28. [PubMed:28956437 ]
Colis LC, Woo CM, Hegan DC, Li Z, Glazer PM, Herzon SB: The cytotoxicity of (-)-lomaiviticin A arises from induction of double-strand breaks in DNA. Nat Chem. 2014 Jun;6(6):504-10. doi: 10.1038/nchem.1944. Epub 2014 May 11. [PubMed:24848236 ]
Lei X, Porco JA Jr: Total synthesis of the diazobenzofluorene antibiotic (-)-kinamycin C1. J Am Chem Soc. 2006 Nov 22;128(46):14790-1. doi: 10.1021/ja066621v. [PubMed:17105273 ]
Hasinoff BB, Wu X, Yalowich JC, Goodfellow V, Laufer RS, Adedayo O, Dmitrienko GI: Kinamycins A and C, bacterial metabolites that contain an unusual diazo group, as potential new anticancer agents: antiproliferative and cell cycle effects. Anticancer Drugs. 2006 Aug;17(7):825-37. doi: 10.1097/01.cad.0000224442.78211.27. [PubMed:16926632 ]

Showing NP-Card for NSC 138425 (NP0062298)

MOL for NP0062298 (NSC 138425)

3D MOL for NP0062298 (NSC 138425)

3D SDF for NP0062298 (NSC 138425)

3D-SDF for NP0062298 (NSC 138425)

PDB for NP0062298 (NSC 138425)

3D PDB for NP0062298 (NSC 138425)

SMILES for NP0062298 (NSC 138425)

INCHI for NP0062298 (NSC 138425)

Structure for NP0062298 (NSC 138425)

3D Structure for NP0062298 (NSC 138425)