NP-MRD: Showing NP-Card for (1s,2r,3r,4r)-2-(acetyloxy)-5-cyano-1,3,7-trihydroxy-3-methyl-6,11-dioxo-1h,2h,4h-benzo[b]carbazol-4-yl 2-methylpropanoate (NP0292767)

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Record Information

Version

2.0

Created at

2022-09-10 00:27:25 UTC

Updated at

2022-09-10 00:27:26 UTC

NP-MRD ID

NP0292767

Secondary Accession Numbers

None

Natural Product Identification

Common Name

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

Description

FL-120C, also known as FL 120C, 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. (1s,2r,3r,4r)-2-(acetyloxy)-5-cyano-1,3,7-trihydroxy-3-methyl-6,11-dioxo-1h,2h,4h-benzo[b]carbazol-4-yl 2-methylpropanoate is found in Streptomyces chattanoogensis. Based on a literature review very few articles have been published on FL-120C.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309102202272D          

 35 38  0  0  1  0            999 V2000
    6.7920    2.3535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3145    1.6808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6583    0.9309    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4931    1.7580    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0155    1.0852    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.1942    1.1624    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.8503    1.9124    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7166    0.4897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8971    0.3944    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7345   -0.4144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4535   -0.8190    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5488   -1.6385    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6440   -2.4580    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.0605   -0.2602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8818   -0.3374    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.2257   -1.0874    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0471   -1.1645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5246   -0.4918    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3909   -1.9145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2123   -1.9917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9134   -2.5872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3594    0.3353    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.0484   -0.1185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1209    0.6528    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9528   -0.6780    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7901   -1.4868    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3336   -0.1327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5519   -0.3963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3892   -1.2051    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0673    0.1489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0953    0.9577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8771    1.2213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4962    0.6761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2780    0.9396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4406    1.7485    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  5  4  1  1  0  0  0
  5  6  1  0  0  0  0
  6  7  1  6  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  3  0  0  0  0
 11 14  1  0  0  0  0
  8 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  6  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  1  0  0  0  0
 15 22  1  0  0  0  0
  5 22  1  0  0  0  0
 22 23  1  1  0  0  0
 22 24  1  6  0  0  0
 10 25  1  0  0  0  0
 25 26  2  0  0  0  0
 25 27  1  0  0  0  0
 27 28  2  0  0  0  0
 28 29  1  0  0  0  0
 28 30  1  0  0  0  0
 30 31  2  0  0  0  0
 31 32  1  0  0  0  0
 32 33  2  0  0  0  0
 27 33  1  0  0  0  0
 33 34  1  0  0  0  0
  9 34  1  0  0  0  0
 34 35  2  0  0  0  0
M  END

     RDKit          3D

 57 60  0  0  0  0  0  0  0  0999 V2000
   -1.7914    5.0710   -2.3000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5788    4.4401   -0.9720 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8477    5.0217    0.1096 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0669    3.1626   -0.8630 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8396    2.5013    0.3781 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5729    2.1494    0.6163 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9047    2.4301    1.9641 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9289    0.7569    0.3568 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1696    0.1520    0.4977 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0319   -1.1648    0.1403 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7395   -1.3672   -0.2121 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.2361   -2.6009   -0.6361 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1732   -3.6414   -1.0081 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0509   -0.1980   -0.0843 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3432    0.1492   -0.3242 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.2693   -0.8936   -0.1314 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1145   -1.3759   -1.1229 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0146   -0.8201   -2.2518 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0648   -2.4697   -0.8580 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0593   -2.0901    0.2412 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4293   -3.7795   -0.5266 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8000    1.3432    0.4781 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.1109    1.8046   -0.1409 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0572    1.0543    1.7998 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1655   -2.1017    0.1745 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9939   -3.2963   -0.1608 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4830   -1.6653    0.5910 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5809   -2.5090    0.6398 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5045   -3.8145    0.2993 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7895   -1.9573    1.0592 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9258   -0.6464    1.4150 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8316    0.1787    1.3624 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6117   -0.3302    0.9508 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4821    0.5971    0.9152 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6026    1.8067    1.2421 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9025    5.6370   -2.5900 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6639    5.7570   -2.2984 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0326    4.2993   -3.0819 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1605    3.2374    1.1496 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2268    2.8552    0.0255 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4232    1.7113    2.4846 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4614    0.4584   -1.4062 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6871   -2.6261   -1.7748 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5383   -1.8940    1.1990 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6100   -1.2054   -0.1387 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7818   -2.9205    0.3163 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0121   -4.2950   -1.4240 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2460   -4.4451   -0.1354 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6615   -3.7120    0.2686 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9308    2.0328   -1.2288 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4865    2.7310    0.3111 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8482    0.9739   -0.1388 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8719    1.4820    2.1563 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7781   -4.3565   -0.0050 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6533   -2.6125    1.0999 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8826   -0.2451    1.7384 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8863    1.2399    1.6376 H   0  0  0  0  0  0  0  0  0  0  0  0
 20 19  1  0
 19 21  1  0
 19 17  1  0
 17 18  2  0
 17 16  1  0
 16 15  1  0
 15 14  1  0
 14  8  2  0
  8  6  1  0
  6  7  1  0
  6  5  1  0
  5  4  1  0
  4  2  1  0
  2  1  1  0
  2  3  2  0
  5 22  1  0
 22 23  1  0
 22 24  1  1
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  3  0
 10 25  1  0
 25 26  2  0
 25 27  1  0
 27 28  2  0
 28 29  1  0
 28 30  1  0
 30 31  2  0
 31 32  1  0
 32 33  2  0
 33 34  1  0
 34 35  2  0
 22 15  1  0
 34  9  1  0
 11 14  1  0
 33 27  1  0
 20 44  1  0
 20 45  1  0
 20 46  1  0
 19 43  1  0
 21 47  1  0
 21 48  1  0
 21 49  1  0
 15 42  1  6
  6 40  1  6
  7 41  1  0
  5 39  1  1
  1 36  1  0
  1 37  1  0
  1 38  1  0
 23 50  1  0
 23 51  1  0
 23 52  1  0
 24 53  1  0
 29 54  1  0
 30 55  1  0
 31 56  1  0
 32 57  1  0
M  END


  Mrv1652309102202272D          

 35 38  0  0  1  0            999 V2000
    6.7920    2.3535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3145    1.6808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6583    0.9309    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4931    1.7580    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0155    1.0852    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.1942    1.1624    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.8503    1.9124    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7166    0.4897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8971    0.3944    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7345   -0.4144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4535   -0.8190    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5488   -1.6385    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6440   -2.4580    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.0605   -0.2602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8818   -0.3374    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.2257   -1.0874    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0471   -1.1645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5246   -0.4918    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3909   -1.9145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2123   -1.9917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9134   -2.5872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3594    0.3353    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.0484   -0.1185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1209    0.6528    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9528   -0.6780    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7901   -1.4868    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3336   -0.1327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5519   -0.3963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3892   -1.2051    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0673    0.1489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0953    0.9577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8771    1.2213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4962    0.6761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2780    0.9396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4406    1.7485    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  5  4  1  1  0  0  0
  5  6  1  0  0  0  0
  6  7  1  6  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  3  0  0  0  0
 11 14  1  0  0  0  0
  8 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  6  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  1  0  0  0  0
 15 22  1  0  0  0  0
  5 22  1  0  0  0  0
 22 23  1  1  0  0  0
 22 24  1  6  0  0  0
 10 25  1  0  0  0  0
 25 26  2  0  0  0  0
 25 27  1  0  0  0  0
 27 28  2  0  0  0  0
 28 29  1  0  0  0  0
 28 30  1  0  0  0  0
 30 31  2  0  0  0  0
 31 32  1  0  0  0  0
 32 33  2  0  0  0  0
 27 33  1  0  0  0  0
 33 34  1  0  0  0  0
  9 34  1  0  0  0  0
 34 35  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0292767

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)C(=O)O[C@@H]1C2=C([C@H](O)[C@@H](OC(C)=O)[C@]1(C)O)C1=C(N2C#N)C(=O)C2=C(O)C=CC=C2C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C24H22N2O9/c1-9(2)23(32)35-21-17-15(20(31)22(24(21,4)33)34-10(3)27)14-16(26(17)8-25)19(30)13-11(18(14)29)6-5-7-12(13)28/h5-7,9,20-22,28,31,33H,1-4H3/t20-,21+,22+,24+/m0/s1

> <INCHI_KEY>
URROGYQLXVLJJM-JVNMPXIPSA-N

> <FORMULA>
C24H22N2O9

> <MOLECULAR_WEIGHT>
482.445

> <EXACT_MASS>
482.132530296

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
57

> <JCHEM_AVERAGE_POLARIZABILITY>
47.64679583531752

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,2R,3R,4R)-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 2-methylpropanoate

> <JCHEM_LOGP>
1.9482090669999994

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.535523685624899

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.738156704825413

> <JCHEM_PKA_STRONGEST_BASIC>
-3.7183186177394925

> <JCHEM_POLAR_SURFACE_AREA>
176.15

> <JCHEM_REFRACTIVITY>
118.57209999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

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

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 10-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-SEP-22         0                                  
HETATM    1  C   UNK     0      12.678   4.393   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      11.787   3.138   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      12.429   1.738   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      10.254   3.282   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       9.362   2.026   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.829   2.170   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       7.187   3.570   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       6.938   0.914   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.408   0.736   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.104  -0.774   0.000  0.00  0.00           C+0
HETATM   11  N   UNK     0       6.447  -1.529   0.000  0.00  0.00           N+0
HETATM   12  C   UNK     0       6.624  -3.059   0.000  0.00  0.00           C+0
HETATM   13  N   UNK     0       6.802  -4.588   0.000  0.00  0.00           N+0
HETATM   14  C   UNK     0       7.580  -0.486   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       9.113  -0.630   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       9.755  -2.030   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      11.288  -2.174   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      12.179  -0.918   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      11.930  -3.574   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      13.463  -3.718   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      11.038  -4.829   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      10.004   0.626   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      11.290  -0.221   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      11.426   1.219   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       3.645  -1.266   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       3.342  -2.775   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       2.489  -0.248   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       1.030  -0.740   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       0.727  -2.250   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      -0.126   0.278   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       0.178   1.788   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       1.637   2.280   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       2.793   1.262   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       4.252   1.754   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0       4.556   3.264   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   22                                                  
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   14                                                  
CONECT    9    8   10   34                                                  
CONECT   10    9   11   25                                                  
CONECT   11   10   12   14                                                  
CONECT   12   11   13                                                       
CONECT   13   12                                                            
CONECT   14   11    8   15                                                  
CONECT   15   14   16   22                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19                                                            
CONECT   22   15    5   23   24                                             
CONECT   23   22                                                            
CONECT   24   22                                                            
CONECT   25   10   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28   33                                                  
CONECT   28   27   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   27   34                                                  
CONECT   34   33    9   35                                                  
CONECT   35   34                                                            
MASTER        0    0    0    0    0    0    0    0   35    0   76    0
END

View in JSmol

Synonyms

Value	Source
FL 120C	MeSH

Chemical Formula

C₂₄H₂₂N₂O₉

Average Mass

482.4450 Da

Monoisotopic Mass

482.13253 Da

IUPAC Name

(1S,2R,3R,4R)-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 2-methylpropanoate

Traditional Name

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

CAS Registry Number

Not Available

SMILES

CC(C)C(=O)O[C@@H]1C2=C([C@H](O)[C@@H](OC(C)=O)[C@]1(C)O)C1=C(N2C#N)C(=O)C2=C(O)C=CC=C2C1=O

InChI Identifier

InChI=1S/C24H22N2O9/c1-9(2)23(32)35-21-17-15(20(31)22(24(21,4)33)34-10(3)27)14-16(26(17)8-25)19(30)13-11(18(14)29)6-5-7-12(13)28/h5-7,9,20-22,28,31,33H,1-4H3/t20-,21+,22+,24+/m0/s1

InChI Key

URROGYQLXVLJJM-JVNMPXIPSA-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	1.95	ChemAxon
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	118.57 m³·mol⁻¹	ChemAxon
Polarizability	47.65 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	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

8430145

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10254660

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1s,2r,3r,4r)-2-(acetyloxy)-5-cyano-1,3,7-trihydroxy-3-methyl-6,11-dioxo-1h,2h,4h-benzo[b]carbazol-4-yl 2-methylpropanoate (NP0292767)

MOL for NP0292767 ((1s,2r,3r,4r)-2-(acetyloxy)-5-cyano-1,3,7-trihydroxy-3-methyl-6,11-dioxo-1h,2h,4h-benzo[b]carbazol-4-yl 2-methylpropanoate)

3D MOL for NP0292767 ((1s,2r,3r,4r)-2-(acetyloxy)-5-cyano-1,3,7-trihydroxy-3-methyl-6,11-dioxo-1h,2h,4h-benzo[b]carbazol-4-yl 2-methylpropanoate)

3D SDF for NP0292767 ((1s,2r,3r,4r)-2-(acetyloxy)-5-cyano-1,3,7-trihydroxy-3-methyl-6,11-dioxo-1h,2h,4h-benzo[b]carbazol-4-yl 2-methylpropanoate)

3D-SDF for NP0292767 ((1s,2r,3r,4r)-2-(acetyloxy)-5-cyano-1,3,7-trihydroxy-3-methyl-6,11-dioxo-1h,2h,4h-benzo[b]carbazol-4-yl 2-methylpropanoate)

PDB for NP0292767 ((1s,2r,3r,4r)-2-(acetyloxy)-5-cyano-1,3,7-trihydroxy-3-methyl-6,11-dioxo-1h,2h,4h-benzo[b]carbazol-4-yl 2-methylpropanoate)

3D PDB for NP0292767 ((1s,2r,3r,4r)-2-(acetyloxy)-5-cyano-1,3,7-trihydroxy-3-methyl-6,11-dioxo-1h,2h,4h-benzo[b]carbazol-4-yl 2-methylpropanoate)

SMILES for NP0292767 ((1s,2r,3r,4r)-2-(acetyloxy)-5-cyano-1,3,7-trihydroxy-3-methyl-6,11-dioxo-1h,2h,4h-benzo[b]carbazol-4-yl 2-methylpropanoate)

INCHI for NP0292767 ((1s,2r,3r,4r)-2-(acetyloxy)-5-cyano-1,3,7-trihydroxy-3-methyl-6,11-dioxo-1h,2h,4h-benzo[b]carbazol-4-yl 2-methylpropanoate)

Structure for NP0292767 ((1s,2r,3r,4r)-2-(acetyloxy)-5-cyano-1,3,7-trihydroxy-3-methyl-6,11-dioxo-1h,2h,4h-benzo[b]carbazol-4-yl 2-methylpropanoate)

3D Structure for NP0292767 ((1s,2r,3r,4r)-2-(acetyloxy)-5-cyano-1,3,7-trihydroxy-3-methyl-6,11-dioxo-1h,2h,4h-benzo[b]carbazol-4-yl 2-methylpropanoate)