NP-MRD: Showing NP-Card for 2-(acetyloxy)-5-cyano-1,3,7-trihydroxy-3-methyl-6,11-dioxo-1h,2h,4h-benzo[b]carbazol-4-yl propanoate (NP0245429)

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Record Information

Version

2.0

Created at

2022-09-07 06:30:29 UTC

Updated at

2022-09-07 06:30:29 UTC

NP-MRD ID

NP0245429

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2-(acetyloxy)-5-cyano-1,3,7-trihydroxy-3-methyl-6,11-dioxo-1h,2h,4h-benzo[b]carbazol-4-yl propanoate

Description

2-(Acetyloxy)-5-cyano-1,3,7-trihydroxy-3-methyl-6,11-dioxo-1H,2H,3H,4H,5H,6H,11H-benzo[b]carbazol-4-yl propanoate belongs to the class of organic compounds known as carbazoles. Carbazoles are compounds containing a three ring system containing a pyrrole ring fused on either side to a benzene ring. 2-(acetyloxy)-5-cyano-1,3,7-trihydroxy-3-methyl-6,11-dioxo-1h,2h,4h-benzo[b]carbazol-4-yl propanoate is found in Streptomyces chattanoogensis. 2-(Acetyloxy)-5-cyano-1,3,7-trihydroxy-3-methyl-6,11-dioxo-1H,2H,3H,4H,5H,6H,11H-benzo[b]carbazol-4-yl propanoate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004171500502D          

 34 37  0  0  0  0            999 V2000
   -0.7383   -5.6148    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0831   -5.5376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4270   -4.7877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0506   -4.1149    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2483   -4.7105    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5922   -3.9606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4136   -3.8834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7574   -3.1335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2799   -2.4607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6237   -1.7108    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4585   -2.5379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9810   -1.8652    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1596   -1.9423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1843   -2.6923    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3180   -1.2696    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1146   -3.2878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3532   -2.9704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4256   -3.7416    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5769   -3.2287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1960   -2.6835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0334   -1.8747    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9778   -2.9471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5969   -2.4018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3787   -2.6654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5413   -3.4742    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9222   -4.0195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0848   -4.8283    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1404   -3.7559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5213   -4.3011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6839   -5.1099    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7395   -4.0376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0205   -4.4422    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9253   -5.2616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8300   -6.0811    0.0000 N   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  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
 11 16  1  0  0  0  0
  6 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
  8 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 26 28  2  0  0  0  0
 22 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 29 31  1  0  0  0  0
 19 31  2  0  0  0  0
 31 32  1  0  0  0  0
  7 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  3  0  0  0  0
M  END

     RDKit          3D

 54 57  0  0  0  0  0  0  0  0999 V2000
   -3.5514    5.0274    0.6954 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0880    3.6583    1.0596 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5775    2.8894   -0.1062 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5298    3.3171   -1.2695 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1255    1.6003    0.1467 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6103    0.7395   -0.8487 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1930    0.4936   -0.5681 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4483   -0.6851   -0.9317 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7682   -0.6154   -0.5363 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8889    0.6187    0.0624 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7051    1.2810    0.0400 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5248    2.5805    0.5860 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4001    3.6407    1.0372 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2169    0.9666    0.5875 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3080    2.0959    1.1302 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3519    0.0574    0.4833 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5976    0.3855    0.9768 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8211    1.5799    1.5857 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6588   -0.5345    0.8474 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5139   -1.7522    0.2494 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2735   -2.0789   -0.2418 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2038   -1.1810   -0.1251 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8919   -1.5373   -0.6495 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7089   -2.6452   -1.2077 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3620   -1.7008   -1.6202 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4722   -1.2982   -2.9538 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7645   -1.7874   -1.0785 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.8884   -2.4916    0.1108 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5724   -3.6896    0.2443 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6769   -4.4020    1.5319 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0868   -4.1120   -0.8009 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4588   -0.4782   -0.9865 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.4060   -0.5257    0.2222 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3247   -0.2780   -2.0881 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7584    5.8083    0.8863 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9043    5.0335   -0.3457 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4179    5.3048    1.3575 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8912    3.0674    1.5440 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2931    3.7780    1.8471 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6522    1.3412   -1.8059 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3370    2.3632    1.8114 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6109   -0.2512    1.2395 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3263   -2.4592    0.1493 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1085   -3.0341   -0.7250 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0618   -2.7064   -1.6206 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3385   -0.3455   -3.0937 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3246   -2.3979   -1.8523 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7258   -4.7951    1.6397 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0187   -5.2692    1.6209 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5433   -3.7077    2.3869 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0996   -1.3797    0.1580 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9012    0.4549    0.3167 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7270   -0.6268    1.1138 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4419    0.6827   -2.2121 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8 25  1  0
 25 26  1  0
 25 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
 29 31  2  0
 27 32  1  0
 32 33  1  0
 32 34  1  6
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  3  0
 10 14  1  0
 14 15  2  0
 14 16  1  0
 16 17  2  0
 17 18  1  0
 17 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 32  6  1  0
 23  9  1  0
 11  7  1  0
 22 16  1  0
  1 35  1  0
  1 36  1  0
  1 37  1  0
  2 38  1  0
  2 39  1  0
  6 40  1  6
 25 45  1  6
 26 46  1  0
 27 47  1  6
 30 48  1  0
 30 49  1  0
 30 50  1  0
 33 51  1  0
 33 52  1  0
 33 53  1  0
 34 54  1  0
 18 41  1  0
 19 42  1  0
 20 43  1  0
 21 44  1  0
M  END


  Mrv1533004171500502D          

 34 37  0  0  0  0            999 V2000
   -0.7383   -5.6148    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0831   -5.5376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4270   -4.7877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0506   -4.1149    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2483   -4.7105    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5922   -3.9606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4136   -3.8834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7574   -3.1335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2799   -2.4607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6237   -1.7108    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4585   -2.5379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9810   -1.8652    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1596   -1.9423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1843   -2.6923    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3180   -1.2696    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1146   -3.2878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3532   -2.9704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4256   -3.7416    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5769   -3.2287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1960   -2.6835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0334   -1.8747    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9778   -2.9471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5969   -2.4018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3787   -2.6654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5413   -3.4742    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9222   -4.0195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0848   -4.8283    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1404   -3.7559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5213   -4.3011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6839   -5.1099    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7395   -4.0376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0205   -4.4422    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9253   -5.2616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8300   -6.0811    0.0000 N   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  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
 11 16  1  0  0  0  0
  6 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
  8 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 26 28  2  0  0  0  0
 22 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 29 31  1  0  0  0  0
 19 31  2  0  0  0  0
 31 32  1  0  0  0  0
  7 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  3  0  0  0  0
M  END
> <DATABASE_ID>
NP0245429

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCC(=O)OC1C2=C(C(O)C(OC(C)=O)C1(C)O)C1=C(N2C#N)C(=O)C2=C(O)C=CC=C2C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C23H20N2O9/c1-4-12(28)34-21-17-15(20(31)22(23(21,3)32)33-9(2)26)14-16(25(17)8-24)19(30)13-10(18(14)29)6-5-7-11(13)27/h5-7,20-22,27,31-32H,4H2,1-3H3

> <INCHI_KEY>
SVEQKWXOEAIICG-UHFFFAOYSA-N

> <FORMULA>
C23H20N2O9

> <MOLECULAR_WEIGHT>
468.418

> <EXACT_MASS>
468.116880232

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
54

> <JCHEM_AVERAGE_POLARIZABILITY>
46.09054433729839

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-(acetyloxy)-5-cyano-1,3,7-trihydroxy-3-methyl-6,11-dioxo-1H,2H,3H,4H,5H,6H,11H-benzo[b]carbazol-4-yl propanoate

> <ALOGPS_LOGP>
1.18

> <JCHEM_LOGP>
1.4052227886666673

> <ALOGPS_LOGS>
-3.31

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.535532185763607

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.738156705604048

> <JCHEM_PKA_STRONGEST_BASIC>
-3.718318493585042

> <JCHEM_POLAR_SURFACE_AREA>
176.15

> <JCHEM_REFRACTIVITY>
113.99759999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.27e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-(acetyloxy)-5-cyano-1,3,7-trihydroxy-3-methyl-6,11-dioxo-1H,2H,4H-benzo[b]carbazol-4-yl propanoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 17-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-APR-15         0                                  
HETATM    1  C   UNK     0      -1.378 -10.481   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.155 -10.337   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.797  -8.937   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      -0.094  -7.681   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0       2.330  -8.793   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       2.972  -7.393   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.505  -7.249   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.147  -5.849   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.256  -4.593   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       4.898  -3.193   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       2.723  -4.737   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       1.831  -3.482   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       0.298  -3.626   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      -0.344  -5.026   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      -0.594  -2.370   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.081  -6.137   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.659  -5.545   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       0.795  -6.984   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       6.677  -6.027   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       7.833  -5.009   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       7.529  -3.499   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       9.292  -5.501   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      10.448  -4.483   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      11.907  -4.975   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      12.210  -6.485   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      11.055  -7.503   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      11.358  -9.013   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       9.595  -7.011   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       8.440  -8.029   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       8.743  -9.539   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       6.980  -7.537   0.000  0.00  0.00           C+0
HETATM   32  N   UNK     0       5.638  -8.292   0.000  0.00  0.00           N+0
HETATM   33  C   UNK     0       5.460  -9.822   0.000  0.00  0.00           C+0
HETATM   34  N   UNK     0       5.283 -11.351   0.000  0.00  0.00           N+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7   16                                                  
CONECT    7    6    8   32                                                  
CONECT    8    7    9   19                                                  
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   16                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13                                                            
CONECT   16   11    6   17   18                                             
CONECT   17   16                                                            
CONECT   18   16                                                            
CONECT   19    8   20   31                                                  
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23   28                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   22   29                                                  
CONECT   29   28   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   19   32                                                  
CONECT   32   31    7   33                                                  
CONECT   33   32   34                                                       
CONECT   34   33                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   74    0
END

View in JSmol

Synonyms

Value	Source
2-(Acetyloxy)-5-cyano-1,3,7-trihydroxy-3-methyl-6,11-dioxo-1H,2H,3H,4H,5H,6H,11H-benzo[b]carbazol-4-yl propanoic acid	Generator

Chemical Formula

C₂₃H₂₀N₂O₉

Average Mass

468.4180 Da

Monoisotopic Mass

468.11688 Da

IUPAC Name

2-(acetyloxy)-5-cyano-1,3,7-trihydroxy-3-methyl-6,11-dioxo-1H,2H,3H,4H,5H,6H,11H-benzo[b]carbazol-4-yl propanoate

Traditional Name

2-(acetyloxy)-5-cyano-1,3,7-trihydroxy-3-methyl-6,11-dioxo-1H,2H,4H-benzo[b]carbazol-4-yl propanoate

CAS Registry Number

Not Available

SMILES

CCC(=O)OC1C2=C(C(O)C(OC(C)=O)C1(C)O)C1=C(N2C#N)C(=O)C2=C(O)C=CC=C2C1=O

InChI Identifier

InChI=1S/C23H20N2O9/c1-4-12(28)34-21-17-15(20(31)22(23(21,3)32)33-9(2)26)14-16(25(17)8-24)19(30)13-10(18(14)29)6-5-7-11(13)27/h5-7,20-22,27,31-32H,4H2,1-3H3

InChI Key

SVEQKWXOEAIICG-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 chattanoogensis	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as carbazoles. Carbazoles are compounds containing a three ring system containing a pyrrole ring fused on either side to a benzene ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indoles and derivatives

Sub Class

Carbazoles

Direct Parent

Carbazoles

Alternative Parents

Substituents

Carbazole
Naphthalene
Aryl ketone
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Dicarboxylic acid or derivatives
Substituted pyrrole
Benzenoid
Pyrrole
Tertiary alcohol
Heteroaromatic compound
Vinylogous acid
Vinylogous amide
Secondary alcohol
Ketone
Carboxylic acid ester
Polyol
Carboxylic acid derivative
Azacycle
Organic oxide
Alcohol
Organooxygen compound
Organonitrogen compound
Organopnictogen compound
Organic oxygen compound
Hydrocarbon derivative
Organic nitrogen compound
Carbonyl group
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	1.18	ALOGPS
logP	1.41	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Acidic)	7.74	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	176.15 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	114 m³·mol⁻¹	ChemAxon
Polarizability	46.09 Å³	ChemAxon
Number of Rings	4	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

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

85135798

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 2-(acetyloxy)-5-cyano-1,3,7-trihydroxy-3-methyl-6,11-dioxo-1h,2h,4h-benzo[b]carbazol-4-yl propanoate (NP0245429)

MOL for NP0245429 (2-(acetyloxy)-5-cyano-1,3,7-trihydroxy-3-methyl-6,11-dioxo-1h,2h,4h-benzo[b]carbazol-4-yl propanoate)

3D MOL for NP0245429 (2-(acetyloxy)-5-cyano-1,3,7-trihydroxy-3-methyl-6,11-dioxo-1h,2h,4h-benzo[b]carbazol-4-yl propanoate)

3D SDF for NP0245429 (2-(acetyloxy)-5-cyano-1,3,7-trihydroxy-3-methyl-6,11-dioxo-1h,2h,4h-benzo[b]carbazol-4-yl propanoate)

3D-SDF for NP0245429 (2-(acetyloxy)-5-cyano-1,3,7-trihydroxy-3-methyl-6,11-dioxo-1h,2h,4h-benzo[b]carbazol-4-yl propanoate)

PDB for NP0245429 (2-(acetyloxy)-5-cyano-1,3,7-trihydroxy-3-methyl-6,11-dioxo-1h,2h,4h-benzo[b]carbazol-4-yl propanoate)

3D PDB for NP0245429 (2-(acetyloxy)-5-cyano-1,3,7-trihydroxy-3-methyl-6,11-dioxo-1h,2h,4h-benzo[b]carbazol-4-yl propanoate)

SMILES for NP0245429 (2-(acetyloxy)-5-cyano-1,3,7-trihydroxy-3-methyl-6,11-dioxo-1h,2h,4h-benzo[b]carbazol-4-yl propanoate)

INCHI for NP0245429 (2-(acetyloxy)-5-cyano-1,3,7-trihydroxy-3-methyl-6,11-dioxo-1h,2h,4h-benzo[b]carbazol-4-yl propanoate)

Structure for NP0245429 (2-(acetyloxy)-5-cyano-1,3,7-trihydroxy-3-methyl-6,11-dioxo-1h,2h,4h-benzo[b]carbazol-4-yl propanoate)

3D Structure for NP0245429 (2-(acetyloxy)-5-cyano-1,3,7-trihydroxy-3-methyl-6,11-dioxo-1h,2h,4h-benzo[b]carbazol-4-yl propanoate)