NP-MRD: Showing NP-Card for JBIR-88 (NP0009372)

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Record Information

Version

2.0

Created at

2020-12-09 06:46:29 UTC

Updated at

2021-07-15 17:03:04 UTC

NP-MRD ID

NP0009372

Secondary Accession Numbers

None

Natural Product Identification

Common Name

JBIR-88

Provided By

NPAtlas

Description

JBIR-88 belongs to the class of organic compounds known as angucyclines. These are polyketides with a structure based on then benz[a]anthracene skeleton, with the particularity that the central ring of the anthracene moiety is a para-quinone. JBIR-88 is found in Streptomyces. JBIR-88 was first documented in 2010 (PMID: 20664606). Based on a literature review very few articles have been published on JBIR-88.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242106353D          

 37 41  0  0  0  0            999 V2000
   -2.8190   -1.8776   -1.2786 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2192   -0.9822   -0.6734 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9744    0.0774   -0.0179 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3028    1.0643    0.6511 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9733    2.0862    1.2847 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3743    2.1430    1.2607 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0683    1.1695    0.5992 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8227    1.2093    0.5487 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -4.3734    0.1249   -0.0480 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1110   -0.7991   -0.6793 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8364    1.0622    0.7113 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3122    1.9780    1.3375 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1059    0.0031    0.0514 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7637   -1.0171   -0.6358 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0419   -2.0221   -1.2334 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6343   -3.0432   -1.9170 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3640   -1.9949   -1.1350 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0385   -1.0095   -0.4720 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2807    0.0250    0.1383 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0362    1.1126    0.7466 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5886    2.2227    0.8554 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3634    0.7313    1.1927 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.0000    0.3289   -0.1988 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5379   -1.0437   -0.3563 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.0988   -1.7442   -1.4171 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6676    1.0876    0.7872 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.0559    0.3136    1.6112 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    4.9850    2.8226    0.4835 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -2.4452    2.8558    1.8068 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9119    2.9437    1.7567 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8805   -1.5756   -1.1730 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5173   -3.2885   -2.1245 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9018   -2.8019   -1.6152 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3172   -0.0958    1.9630 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6454    0.9456   -1.0870 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7462   -1.6472    0.5713 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8605   -1.3645   -2.2949 H   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  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  2  0  0  0  0
  9 10  1  0  0  0  0
  4 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  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  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 23 26  1  0  0  0  0
 26 27  1  1  0  0  0
 26 28  1  0  0  0  0
 14  2  1  0  0  0  0
 24 18  1  0  0  0  0
  9  3  1  0  0  0  0
 19 13  1  0  0  0  0
 26 22  1  0  0  0  0
  5 29  1  0  0  0  0
  6 30  1  0  0  0  0
 10 31  1  0  0  0  0
 16 32  1  0  0  0  0
 17 33  1  0  0  0  0
 22 34  1  1  0  0  0
 23 35  1  6  0  0  0
 24 36  1  1  0  0  0
 25 37  1  0  0  0  0
M  END

     RDKit          3D

 37 41  0  0  0  0  0  0  0  0999 V2000
   -2.8190   -1.8776   -1.2786 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2192   -0.9822   -0.6734 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9744    0.0774   -0.0179 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3028    1.0643    0.6511 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9733    2.0862    1.2847 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3743    2.1430    1.2607 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0683    1.1695    0.5992 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8227    1.2093    0.5487 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -4.3734    0.1249   -0.0480 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1110   -0.7991   -0.6793 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8364    1.0622    0.7113 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3122    1.9780    1.3375 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1059    0.0031    0.0514 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7637   -1.0171   -0.6358 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0419   -2.0221   -1.2334 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6343   -3.0432   -1.9170 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3640   -1.9949   -1.1350 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0385   -1.0095   -0.4720 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2807    0.0250    0.1383 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0362    1.1126    0.7466 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5886    2.2227    0.8554 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3634    0.7313    1.1927 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.0000    0.3289   -0.1988 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5379   -1.0437   -0.3563 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.0988   -1.7442   -1.4171 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6676    1.0876    0.7872 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.0559    0.3136    1.6112 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    4.9850    2.8226    0.4835 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -2.4452    2.8558    1.8068 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9119    2.9437    1.7567 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8805   -1.5756   -1.1730 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5173   -3.2885   -2.1245 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9018   -2.8019   -1.6152 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3172   -0.0958    1.9630 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6454    0.9456   -1.0870 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7462   -1.6472    0.5713 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8605   -1.3645   -2.2949 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  7  9  2  0
  9 10  1  0
  4 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 15 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 20 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 23 26  1  0
 26 27  1  1
 26 28  1  0
 14  2  1  0
 24 18  1  0
  9  3  1  0
 19 13  1  0
 26 22  1  0
  5 29  1  0
  6 30  1  0
 10 31  1  0
 16 32  1  0
 17 33  1  0
 22 34  1  1
 23 35  1  6
 24 36  1  1
 25 37  1  0
M  END


  Mrv1652306242106353D          

 37 41  0  0  0  0            999 V2000
   -2.8190   -1.8776   -1.2786 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2192   -0.9822   -0.6734 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9744    0.0774   -0.0179 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3028    1.0643    0.6511 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9733    2.0862    1.2847 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3743    2.1430    1.2607 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0683    1.1695    0.5992 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8227    1.2093    0.5487 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -4.3734    0.1249   -0.0480 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1110   -0.7991   -0.6793 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8364    1.0622    0.7113 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3122    1.9780    1.3375 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1059    0.0031    0.0514 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7637   -1.0171   -0.6358 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0419   -2.0221   -1.2334 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6343   -3.0432   -1.9170 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3640   -1.9949   -1.1350 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0385   -1.0095   -0.4720 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2807    0.0250    0.1383 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0362    1.1126    0.7466 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5886    2.2227    0.8554 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3634    0.7313    1.1927 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.0000    0.3289   -0.1988 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5379   -1.0437   -0.3563 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.0988   -1.7442   -1.4171 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6676    1.0876    0.7872 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.0559    0.3136    1.6112 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    4.9850    2.8226    0.4835 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -2.4452    2.8558    1.8068 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9119    2.9437    1.7567 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8805   -1.5756   -1.1730 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5173   -3.2885   -2.1245 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9018   -2.8019   -1.6152 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3172   -0.0958    1.9630 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6454    0.9456   -1.0870 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7462   -1.6472    0.5713 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8605   -1.3645   -2.2949 H   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  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  2  0  0  0  0
  9 10  1  0  0  0  0
  4 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  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  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 23 26  1  0  0  0  0
 26 27  1  1  0  0  0
 26 28  1  0  0  0  0
 14  2  1  0  0  0  0
 24 18  1  0  0  0  0
  9  3  1  0  0  0  0
 19 13  1  0  0  0  0
 26 22  1  0  0  0  0
  5 29  1  0  0  0  0
  6 30  1  0  0  0  0
 10 31  1  0  0  0  0
 16 32  1  0  0  0  0
 17 33  1  0  0  0  0
 22 34  1  1  0  0  0
 23 35  1  6  0  0  0
 24 36  1  1  0  0  0
 25 37  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0009372

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C([H])C2=C(C(=O)[C@@]3([H])[C@]([H])([C@]2([H])O[H])C3(Cl)Cl)C2=C1C(=O)C1=C(C([H])=C([H])C(Cl)=C1O[H])C2=O

> <INCHI_IDENTIFIER>
InChI=1S/C19H9Cl3O6/c20-6-2-1-4-9(16(6)26)17(27)10-7(23)3-5-8(11(10)14(4)24)18(28)13-12(15(5)25)19(13,21)22/h1-3,12-13,15,23,25-26H/t12-,13-,15-/m1/s1

> <INCHI_KEY>
HIUKLKLVZUROPQ-UHFFFAOYSA-N

> <FORMULA>
C19H9Cl3O6

> <MOLECULAR_WEIGHT>
439.63

> <EXACT_MASS>
437.9464711

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
37

> <JCHEM_AVERAGE_POLARIZABILITY>
39.994454708945135

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(4R,6R,7S)-5,5,15-trichloro-7,10,14-trihydroxypentacyclo[9.8.0.0^{2,8}.0^{4,6}.0^{13,18}]nonadeca-1(11),2(8),9,13(18),14,16-hexaene-3,12,19-trione

> <ALOGPS_LOGP>
3.49

> <JCHEM_LOGP>
4.4061018

> <ALOGPS_LOGS>
-3.82

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
6.745137246327407

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.089380262329637

> <JCHEM_PKA_STRONGEST_BASIC>
-3.387313834676097

> <JCHEM_POLAR_SURFACE_AREA>
111.89999999999999

> <JCHEM_REFRACTIVITY>
102.0971

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.64e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(4R,6R,7S)-5,5,15-trichloro-7,10,14-trihydroxypentacyclo[9.8.0.0^{2,8}.0^{4,6}.0^{13,18}]nonadeca-1(11),2(8),9,13(18),14,16-hexaene-3,12,19-trione

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 37 41  0  0  0  0  0  0  0  0999 V2000
   -2.8190   -1.8776   -1.2786 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2192   -0.9822   -0.6734 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9744    0.0774   -0.0179 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3028    1.0643    0.6511 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9733    2.0862    1.2847 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3743    2.1430    1.2607 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0683    1.1695    0.5992 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8227    1.2093    0.5487 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -4.3734    0.1249   -0.0480 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1110   -0.7991   -0.6793 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8364    1.0622    0.7113 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3122    1.9780    1.3375 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1059    0.0031    0.0514 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7637   -1.0171   -0.6358 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0419   -2.0221   -1.2334 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6343   -3.0432   -1.9170 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3640   -1.9949   -1.1350 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0385   -1.0095   -0.4720 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2807    0.0250    0.1383 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0362    1.1126    0.7466 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5886    2.2227    0.8554 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3634    0.7313    1.1927 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.0000    0.3289   -0.1988 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5379   -1.0437   -0.3563 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.0988   -1.7442   -1.4171 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6676    1.0876    0.7872 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.0559    0.3136    1.6112 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    4.9850    2.8226    0.4835 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -2.4452    2.8558    1.8068 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9119    2.9437    1.7567 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8805   -1.5756   -1.1730 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5173   -3.2885   -2.1245 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9018   -2.8019   -1.6152 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3172   -0.0958    1.9630 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6454    0.9456   -1.0870 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7462   -1.6472    0.5713 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8605   -1.3645   -2.2949 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  7  9  2  0
  9 10  1  0
  4 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 15 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 20 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 23 26  1  0
 26 27  1  1
 26 28  1  0
 14  2  1  0
 24 18  1  0
  9  3  1  0
 19 13  1  0
 26 22  1  0
  5 29  1  0
  6 30  1  0
 10 31  1  0
 16 32  1  0
 17 33  1  0
 22 34  1  1
 23 35  1  6
 24 36  1  1
 25 37  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  O   UNK     0      -2.819  -1.878  -1.279  0.00  0.00           O+0
HETATM    2  C   UNK     0      -2.219  -0.982  -0.673  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.974   0.077  -0.018  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.303   1.064   0.651  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.973   2.086   1.285  0.00  0.00           C+0
HETATM    6  C   UNK     0      -4.374   2.143   1.261  0.00  0.00           C+0
HETATM    7  C   UNK     0      -5.068   1.169   0.599  0.00  0.00           C+0
HETATM    8 Cl   UNK     0      -6.823   1.209   0.549  0.00  0.00          Cl+0
HETATM    9  C   UNK     0      -4.373   0.125  -0.048  0.00  0.00           C+0
HETATM   10  O   UNK     0      -5.111  -0.799  -0.679  0.00  0.00           O+0
HETATM   11  C   UNK     0      -0.836   1.062   0.711  0.00  0.00           C+0
HETATM   12  O   UNK     0      -0.312   1.978   1.337  0.00  0.00           O+0
HETATM   13  C   UNK     0      -0.106   0.003   0.051  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.764  -1.017  -0.636  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.042  -2.022  -1.233  0.00  0.00           C+0
HETATM   16  O   UNK     0      -0.634  -3.043  -1.917  0.00  0.00           O+0
HETATM   17  C   UNK     0       1.364  -1.995  -1.135  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.038  -1.010  -0.472  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.281   0.025   0.138  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.036   1.113   0.747  0.00  0.00           C+0
HETATM   21  O   UNK     0       1.589   2.223   0.855  0.00  0.00           O+0
HETATM   22  C   UNK     0       3.363   0.731   1.193  0.00  0.00           C+0
HETATM   23  C   UNK     0       4.000   0.329  -0.199  0.00  0.00           C+0
HETATM   24  C   UNK     0       3.538  -1.044  -0.356  0.00  0.00           C+0
HETATM   25  O   UNK     0       4.099  -1.744  -1.417  0.00  0.00           O+0
HETATM   26  C   UNK     0       4.668   1.088   0.787  0.00  0.00           C+0
HETATM   27 Cl   UNK     0       6.056   0.314   1.611  0.00  0.00          Cl+0
HETATM   28 Cl   UNK     0       4.985   2.823   0.484  0.00  0.00          Cl+0
HETATM   29  H   UNK     0      -2.445   2.856   1.807  0.00  0.00           H+0
HETATM   30  H   UNK     0      -4.912   2.944   1.757  0.00  0.00           H+0
HETATM   31  H   UNK     0      -4.880  -1.576  -1.173  0.00  0.00           H+0
HETATM   32  H   UNK     0      -1.517  -3.289  -2.124  0.00  0.00           H+0
HETATM   33  H   UNK     0       1.902  -2.802  -1.615  0.00  0.00           H+0
HETATM   34  H   UNK     0       3.317  -0.096   1.963  0.00  0.00           H+0
HETATM   35  H   UNK     0       3.645   0.946  -1.087  0.00  0.00           H+0
HETATM   36  H   UNK     0       3.746  -1.647   0.571  0.00  0.00           H+0
HETATM   37  H   UNK     0       3.861  -1.365  -2.295  0.00  0.00           H+0
CONECT    1    2                                                            
CONECT    2    1    3   14                                                  
CONECT    3    2    4    9                                                  
CONECT    4    3    5   11                                                  
CONECT    5    4    6   29                                                  
CONECT    6    5    7   30                                                  
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10    3                                                  
CONECT   10    9   31                                                       
CONECT   11    4   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   19                                                  
CONECT   14   13   15    2                                                  
CONECT   15   14   16   17                                                  
CONECT   16   15   32                                                       
CONECT   17   15   18   33                                                  
CONECT   18   17   19   24                                                  
CONECT   19   18   20   13                                                  
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23   26   34                                             
CONECT   23   22   24   26   35                                             
CONECT   24   23   25   18   36                                             
CONECT   25   24   37                                                       
CONECT   26   23   27   28   22                                             
CONECT   27   26                                                            
CONECT   28   26                                                            
CONECT   29    5                                                            
CONECT   30    6                                                            
CONECT   31   10                                                            
CONECT   32   16                                                            
CONECT   33   17                                                            
CONECT   34   22                                                            
CONECT   35   23                                                            
CONECT   36   24                                                            
CONECT   37   25                                                            
MASTER        0    0    0    0    0    0    0    0   37    0   82    0
END

RDKit          3D

37 41  0  0  0  0  0  0  0  0999 V2000
   -2.8190   -1.8776   -1.2786 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2192   -0.9822   -0.6734 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9744    0.0774   -0.0179 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3028    1.0643    0.6511 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9733    2.0862    1.2847 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3743    2.1430    1.2607 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0683    1.1695    0.5992 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8227    1.2093    0.5487 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -4.3734    0.1249   -0.0480 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1110   -0.7991   -0.6793 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8364    1.0622    0.7113 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3122    1.9780    1.3375 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1059    0.0031    0.0514 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7637   -1.0171   -0.6358 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0419   -2.0221   -1.2334 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6343   -3.0432   -1.9170 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3640   -1.9949   -1.1350 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0385   -1.0095   -0.4720 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2807    0.0250    0.1383 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0362    1.1126    0.7466 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5886    2.2227    0.8554 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3634    0.7313    1.1927 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.0000    0.3289   -0.1988 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5379   -1.0437   -0.3563 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.0988   -1.7442   -1.4171 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6676    1.0876    0.7872 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.0559    0.3136    1.6112 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    4.9850    2.8226    0.4835 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -2.4452    2.8558    1.8068 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9119    2.9437    1.7567 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8805   -1.5756   -1.1730 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5173   -3.2885   -2.1245 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9018   -2.8019   -1.6152 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3172   -0.0958    1.9630 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6454    0.9456   -1.0870 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7462   -1.6472    0.5713 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8605   -1.3645   -2.2949 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  7  9  2  0
  9 10  1  0
  4 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 15 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 20 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 23 26  1  0
 26 27  1  1
 26 28  1  0
 14  2  1  0
 24 18  1  0
  9  3  1  0
 19 13  1  0
 26 22  1  0
  5 29  1  0
  6 30  1  0
 10 31  1  0
 16 32  1  0
 17 33  1  0
 22 34  1  1
 23 35  1  6
 24 36  1  1
 25 37  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Not Available

Chemical Formula

C₁₉H₉Cl₃O₆

Average Mass

439.6300 Da

Monoisotopic Mass

437.94647 Da

IUPAC Name

(4R,6R,7S)-5,5,15-trichloro-7,10,14-trihydroxypentacyclo[9.8.0.0^{2,8}.0^{4,6}.0^{13,18}]nonadeca-1(11),2(8),9,13(18),14,16-hexaene-3,12,19-trione

Traditional Name

(4R,6R,7S)-5,5,15-trichloro-7,10,14-trihydroxypentacyclo[9.8.0.0^{2,8}.0^{4,6}.0^{13,18}]nonadeca-1(11),2(8),9,13(18),14,16-hexaene-3,12,19-trione

CAS Registry Number

Not Available

SMILES

OC1C2C(C(=O)C3=C4C(=O)C5=C(C(O)=C(Cl)C=C5)C(=O)C4=C(O)C=C13)C2(Cl)Cl

InChI Identifier

InChI=1S/C19H9Cl3O6/c20-6-2-1-4-9(16(6)26)17(27)10-7(23)3-5-8(11(10)14(4)24)18(28)13-12(15(5)25)19(13,21)22/h1-3,12-13,15,23,25-26H

InChI Key

HIUKLKLVZUROPQ-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, 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	20664606

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as angucyclines. These are polyketides with a structure based on then benz[a]anthracene skeleton, with the particularity that the central ring of the anthracene moiety is a para-quinone.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Angucyclines

Sub Class

Not Available

Direct Parent

Angucyclines

Alternative Parents

Substituents

Angucycline core
9,10-anthraquinone
Anthraquinone
Phenanthrol
Anthracene
Phenanthrene
Tetralin
2-halophenol
Aryl alkyl ketone
Aryl ketone
Phenol
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Benzenoid
Aryl chloride
Aryl halide
Vinylogous acid
Secondary alcohol
Ketone
Polyol
Alkyl halide
Alcohol
Organohalogen compound
Organochloride
Organic oxygen compound
Organooxygen compound
Organic oxide
Alkyl chloride
Hydrocarbon derivative
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic 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	3.49	ALOGPS
logP	4.41	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Acidic)	6.09	ChemAxon
pKa (Strongest Basic)	-3.4	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	111.9 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	102.1 m³·mol⁻¹	ChemAxon
Polarizability	39.99 Å³	ChemAxon
Number of Rings	5	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

NPA019195

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

28288015

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

49780532

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Motohashi K, Takagi M, Yamamura H, Hayakawa M, Shin-ya K: A new angucycline and a new butenolide isolated from lichen-derived Streptomyces spp. J Antibiot (Tokyo). 2010 Sep;63(9):545-8. doi: 10.1038/ja.2010.94. Epub 2010 Jul 28. [PubMed:20664606 ]

Showing NP-Card for JBIR-88 (NP0009372)

MOL for NP0009372 (JBIR-88)

3D MOL for NP0009372 (JBIR-88)

3D SDF for NP0009372 (JBIR-88)

3D-SDF for NP0009372 (JBIR-88)

PDB for NP0009372 (JBIR-88)

3D PDB for NP0009372 (JBIR-88)

SMILES for NP0009372 (JBIR-88)

INCHI for NP0009372 (JBIR-88)

Structure for NP0009372 (JBIR-88)

3D Structure for NP0009372 (JBIR-88)