NP-MRD: Showing NP-Card for Chlorizidine A (NP0011496)

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Record Information

Version

1.0

Created at

2021-01-05 21:09:55 UTC

Updated at

2021-07-15 17:09:06 UTC

NP-MRD ID

NP0011496

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Chlorizidine A

Provided By

NPAtlas

Description

Chlorizidine A belongs to the class of organic compounds known as isoindolones. These are aromatic polycyclic compounds that an isoindole bearing a ketone. Chlorizidine A is found in Streptomyces sp. It was first documented in 2013 (PMID: 23405849). Based on a literature review very few articles have been published on Chlorizidine A.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242116563D          

 37 41  0  0  0  0            999 V2000
    2.0456    0.8284    2.6000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3729    0.3779    1.4653 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4455    0.0919    0.3593 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1882   -0.3825   -0.7000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5917   -0.7344   -1.8816 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1937   -0.5988   -1.9876 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3222   -0.9740   -3.2115 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5334   -0.1233   -0.9200 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9953    0.0140   -1.0231 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.4222    1.4389   -1.2865 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.6420    1.6513   -0.4475 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.5677    0.5571    0.5452 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1569    0.1572    1.7341 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5647   -1.0223    2.1181 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9777   -1.9084    3.5556 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -2.6338   -1.3082    1.1564 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6071   -2.7453    1.2161 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -2.6409   -0.3531    0.2121 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0989    0.2306    0.2797 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7137    0.6986    1.2983 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5995   -0.4010   -0.2719 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8587   -0.7244   -0.7420 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7479   -0.4593    0.2917 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4864   -0.6817    0.2606 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    4.9858    0.0068    1.3240 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6481    0.4874    2.8761 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.6707    0.0454    0.9867 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1687   -1.1082   -2.7187 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2884   -0.9113   -3.4056 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3526   -0.5965   -1.8710 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7286    1.5900   -2.3628 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6155    2.1682   -1.0871 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5861    1.4828   -1.0262 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6671    2.6525   -0.0068 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9437    0.7119    2.2349 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2624    0.9563    2.1696 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1196   -1.1146   -1.7341 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
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  2  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
  8 19  2  0  0  0  0
 19 20  1  0  0  0  0
  4 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 23 25  2  0  0  0  0
 25 26  1  0  0  0  0
 25 27  1  0  0  0  0
 27  2  1  0  0  0  0
 19  3  1  0  0  0  0
 27 21  1  0  0  0  0
 18  9  1  0  0  0  0
 18 12  1  0  0  0  0
  5 28  1  0  0  0  0
  7 29  1  0  0  0  0
  9 30  1  6  0  0  0
 10 31  1  0  0  0  0
 10 32  1  0  0  0  0
 11 33  1  0  0  0  0
 11 34  1  0  0  0  0
 13 35  1  0  0  0  0
 20 36  1  0  0  0  0
 22 37  1  0  0  0  0
M  END

     RDKit          3D

 37 41  0  0  0  0  0  0  0  0999 V2000
    2.0456    0.8284    2.6000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3729    0.3779    1.4653 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4455    0.0919    0.3593 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1882   -0.3825   -0.7000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5917   -0.7344   -1.8816 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1937   -0.5988   -1.9876 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3222   -0.9740   -3.2115 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5334   -0.1233   -0.9200 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9953    0.0140   -1.0231 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.4222    1.4389   -1.2865 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6420    1.6513   -0.4475 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5677    0.5571    0.5452 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1569    0.1572    1.7341 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5647   -1.0223    2.1181 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9777   -1.9084    3.5556 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -2.6338   -1.3082    1.1564 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6071   -2.7453    1.2161 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -2.6409   -0.3531    0.2121 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0989    0.2306    0.2797 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7137    0.6986    1.2983 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5995   -0.4010   -0.2719 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8587   -0.7244   -0.7420 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7479   -0.4593    0.2917 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4864   -0.6817    0.2606 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    4.9858    0.0068    1.3240 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6481    0.4874    2.8761 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.6707    0.0454    0.9867 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1687   -1.1082   -2.7187 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2884   -0.9113   -3.4056 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3526   -0.5965   -1.8710 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7286    1.5900   -2.3628 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6155    2.1682   -1.0871 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5861    1.4828   -1.0262 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6671    2.6525   -0.0068 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9437    0.7119    2.2349 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2624    0.9563    2.1696 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1196   -1.1146   -1.7341 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
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 14 16  2  0
 16 17  1  0
 16 18  1  0
  8 19  2  0
 19 20  1  0
  4 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  1  0
 23 25  2  0
 25 26  1  0
 25 27  1  0
 27  2  1  0
 19  3  1  0
 27 21  1  0
 18  9  1  0
 18 12  1  0
  5 28  1  0
  7 29  1  0
  9 30  1  6
 10 31  1  0
 10 32  1  0
 11 33  1  0
 11 34  1  0
 13 35  1  0
 20 36  1  0
 22 37  1  0
M  END


  Mrv1652306242116563D          

 37 41  0  0  0  0            999 V2000
    2.0456    0.8284    2.6000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3729    0.3779    1.4653 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4455    0.0919    0.3593 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1882   -0.3825   -0.7000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5917   -0.7344   -1.8816 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1937   -0.5988   -1.9876 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3222   -0.9740   -3.2115 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5334   -0.1233   -0.9200 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9953    0.0140   -1.0231 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.4222    1.4389   -1.2865 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.6420    1.6513   -0.4475 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.5677    0.5571    0.5452 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1569    0.1572    1.7341 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5647   -1.0223    2.1181 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9777   -1.9084    3.5556 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -2.6338   -1.3082    1.1564 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6071   -2.7453    1.2161 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -2.6409   -0.3531    0.2121 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0989    0.2306    0.2797 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7137    0.6986    1.2983 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5995   -0.4010   -0.2719 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8587   -0.7244   -0.7420 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7479   -0.4593    0.2917 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4864   -0.6817    0.2606 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    4.9858    0.0068    1.3240 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6481    0.4874    2.8761 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.6707    0.0454    0.9867 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1687   -1.1082   -2.7187 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2884   -0.9113   -3.4056 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3526   -0.5965   -1.8710 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7286    1.5900   -2.3628 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6155    2.1682   -1.0871 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5861    1.4828   -1.0262 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6671    2.6525   -0.0068 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9437    0.7119    2.2349 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2624    0.9563    2.1696 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1196   -1.1146   -1.7341 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
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  2  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
  8 19  2  0  0  0  0
 19 20  1  0  0  0  0
  4 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 23 25  2  0  0  0  0
 25 26  1  0  0  0  0
 25 27  1  0  0  0  0
 27  2  1  0  0  0  0
 19  3  1  0  0  0  0
 27 21  1  0  0  0  0
 18  9  1  0  0  0  0
 18 12  1  0  0  0  0
  5 28  1  0  0  0  0
  7 29  1  0  0  0  0
  9 30  1  6  0  0  0
 10 31  1  0  0  0  0
 10 32  1  0  0  0  0
 11 33  1  0  0  0  0
 11 34  1  0  0  0  0
 13 35  1  0  0  0  0
 20 36  1  0  0  0  0
 22 37  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0011496

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C([H])C2=C(C(=O)N3C(Cl)=C(Cl)C([H])=C23)C(O[H])=C1[C@@]1([H])N2C(Cl)=C(Cl)C([H])=C2C([H])([H])C1([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C18H10Cl4N2O3/c19-8-3-6-1-2-10(23(6)16(8)21)14-12(25)4-7-11-5-9(20)17(22)24(11)18(27)13(7)15(14)26/h3-5,10,25-26H,1-2H2/t10-/m0/s1

> <INCHI_KEY>
PNWJMZXCEYWQFJ-JTQLQIEISA-N

> <FORMULA>
C18H10Cl4N2O3

> <MOLECULAR_WEIGHT>
444.09

> <EXACT_MASS>
441.944553

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
37

> <JCHEM_AVERAGE_POLARIZABILITY>
41.600196832976664

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2,3-dichloro-7-[(3S)-5,6-dichloro-2,3-dihydro-1H-pyrrolizin-3-yl]-6,8-dihydroxy-5H-benzo[a]pyrrolizin-5-one

> <ALOGPS_LOGP>
5.47

> <JCHEM_LOGP>
4.39651472

> <ALOGPS_LOGS>
-4.44

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.447401670736289

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.92992610819336

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6222741666389715

> <JCHEM_POLAR_SURFACE_AREA>
67.38999999999999

> <JCHEM_REFRACTIVITY>
104.7769

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.60e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2,3-dichloro-7-[(3S)-5,6-dichloro-2,3-dihydro-1H-pyrrolizin-3-yl]-6,8-dihydroxybenzo[a]pyrrolizin-5-one

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 37 41  0  0  0  0  0  0  0  0999 V2000
    2.0456    0.8284    2.6000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3729    0.3779    1.4653 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4455    0.0919    0.3593 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1882   -0.3825   -0.7000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5917   -0.7344   -1.8816 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1937   -0.5988   -1.9876 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3222   -0.9740   -3.2115 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5334   -0.1233   -0.9200 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9953    0.0140   -1.0231 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.4222    1.4389   -1.2865 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6420    1.6513   -0.4475 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5677    0.5571    0.5452 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1569    0.1572    1.7341 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5647   -1.0223    2.1181 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9777   -1.9084    3.5556 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -2.6338   -1.3082    1.1564 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6071   -2.7453    1.2161 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -2.6409   -0.3531    0.2121 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0989    0.2306    0.2797 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7137    0.6986    1.2983 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5995   -0.4010   -0.2719 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8587   -0.7244   -0.7420 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7479   -0.4593    0.2917 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4864   -0.6817    0.2606 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    4.9858    0.0068    1.3240 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6481    0.4874    2.8761 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.6707    0.0454    0.9867 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1687   -1.1082   -2.7187 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2884   -0.9113   -3.4056 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3526   -0.5965   -1.8710 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7286    1.5900   -2.3628 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6155    2.1682   -1.0871 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5861    1.4828   -1.0262 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6671    2.6525   -0.0068 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9437    0.7119    2.2349 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2624    0.9563    2.1696 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1196   -1.1146   -1.7341 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
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 14 16  2  0
 16 17  1  0
 16 18  1  0
  8 19  2  0
 19 20  1  0
  4 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  1  0
 23 25  2  0
 25 26  1  0
 25 27  1  0
 27  2  1  0
 19  3  1  0
 27 21  1  0
 18  9  1  0
 18 12  1  0
  5 28  1  0
  7 29  1  0
  9 30  1  6
 10 31  1  0
 10 32  1  0
 11 33  1  0
 11 34  1  0
 13 35  1  0
 20 36  1  0
 22 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       2.046   0.828   2.600  0.00  0.00           O+0
HETATM    2  C   UNK     0       2.373   0.378   1.465  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.446   0.092   0.359  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.188  -0.383  -0.700  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.592  -0.734  -1.882  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.194  -0.599  -1.988  0.00  0.00           C+0
HETATM    7  O   UNK     0      -0.322  -0.974  -3.212  0.00  0.00           O+0
HETATM    8  C   UNK     0      -0.533  -0.123  -0.920  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.995   0.014  -1.023  0.00  0.00           C+0
HETATM   10  C   UNK     0      -2.422   1.439  -1.287  0.00  0.00           C+0
HETATM   11  C   UNK     0      -3.642   1.651  -0.448  0.00  0.00           C+0
HETATM   12  C   UNK     0      -3.568   0.557   0.545  0.00  0.00           C+0
HETATM   13  C   UNK     0      -4.157   0.157   1.734  0.00  0.00           C+0
HETATM   14  C   UNK     0      -3.565  -1.022   2.118  0.00  0.00           C+0
HETATM   15 Cl   UNK     0      -3.978  -1.908   3.556  0.00  0.00          Cl+0
HETATM   16  C   UNK     0      -2.634  -1.308   1.156  0.00  0.00           C+0
HETATM   17 Cl   UNK     0      -1.607  -2.745   1.216  0.00  0.00          Cl+0
HETATM   18  N   UNK     0      -2.641  -0.353   0.212  0.00  0.00           N+0
HETATM   19  C   UNK     0       0.099   0.231   0.280  0.00  0.00           C+0
HETATM   20  O   UNK     0      -0.714   0.699   1.298  0.00  0.00           O+0
HETATM   21  C   UNK     0       3.599  -0.401  -0.272  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.859  -0.724  -0.742  0.00  0.00           C+0
HETATM   23  C   UNK     0       5.748  -0.459   0.292  0.00  0.00           C+0
HETATM   24 Cl   UNK     0       7.486  -0.682   0.261  0.00  0.00          Cl+0
HETATM   25  C   UNK     0       4.986   0.007   1.324  0.00  0.00           C+0
HETATM   26 Cl   UNK     0       5.648   0.487   2.876  0.00  0.00          Cl+0
HETATM   27  N   UNK     0       3.671   0.045   0.987  0.00  0.00           N+0
HETATM   28  H   UNK     0       2.169  -1.108  -2.719  0.00  0.00           H+0
HETATM   29  H   UNK     0      -1.288  -0.911  -3.406  0.00  0.00           H+0
HETATM   30  H   UNK     0      -2.353  -0.597  -1.871  0.00  0.00           H+0
HETATM   31  H   UNK     0      -2.729   1.590  -2.363  0.00  0.00           H+0
HETATM   32  H   UNK     0      -1.615   2.168  -1.087  0.00  0.00           H+0
HETATM   33  H   UNK     0      -4.586   1.483  -1.026  0.00  0.00           H+0
HETATM   34  H   UNK     0      -3.667   2.652  -0.007  0.00  0.00           H+0
HETATM   35  H   UNK     0      -4.944   0.712   2.235  0.00  0.00           H+0
HETATM   36  H   UNK     0      -0.262   0.956   2.170  0.00  0.00           H+0
HETATM   37  H   UNK     0       5.120  -1.115  -1.734  0.00  0.00           H+0
CONECT    1    2                                                            
CONECT    2    1    3   27                                                  
CONECT    3    2    4   19                                                  
CONECT    4    3    5   21                                                  
CONECT    5    4    6   28                                                  
CONECT    6    5    7    8                                                  
CONECT    7    6   29                                                       
CONECT    8    6    9   19                                                  
CONECT    9    8   10   18   30                                             
CONECT   10    9   11   31   32                                             
CONECT   11   10   12   33   34                                             
CONECT   12   11   13   18                                                  
CONECT   13   12   14   35                                                  
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16    9   12                                                  
CONECT   19    8   20    3                                                  
CONECT   20   19   36                                                       
CONECT   21    4   22   27                                                  
CONECT   22   21   23   37                                                  
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25    2   21                                                  
CONECT   28    5                                                            
CONECT   29    7                                                            
CONECT   30    9                                                            
CONECT   31   10                                                            
CONECT   32   10                                                            
CONECT   33   11                                                            
CONECT   34   11                                                            
CONECT   35   13                                                            
CONECT   36   20                                                            
CONECT   37   22                                                            
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
    2.0456    0.8284    2.6000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3729    0.3779    1.4653 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4455    0.0919    0.3593 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1882   -0.3825   -0.7000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5917   -0.7344   -1.8816 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1937   -0.5988   -1.9876 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3222   -0.9740   -3.2115 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5334   -0.1233   -0.9200 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9953    0.0140   -1.0231 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.4222    1.4389   -1.2865 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6420    1.6513   -0.4475 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5677    0.5571    0.5452 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1569    0.1572    1.7341 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5647   -1.0223    2.1181 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9777   -1.9084    3.5556 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -2.6338   -1.3082    1.1564 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6071   -2.7453    1.2161 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -2.6409   -0.3531    0.2121 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0989    0.2306    0.2797 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7137    0.6986    1.2983 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5995   -0.4010   -0.2719 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8587   -0.7244   -0.7420 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7479   -0.4593    0.2917 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4864   -0.6817    0.2606 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    4.9858    0.0068    1.3240 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6481    0.4874    2.8761 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.6707    0.0454    0.9867 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1687   -1.1082   -2.7187 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2884   -0.9113   -3.4056 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3526   -0.5965   -1.8710 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7286    1.5900   -2.3628 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6155    2.1682   -1.0871 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5861    1.4828   -1.0262 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6671    2.6525   -0.0068 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9437    0.7119    2.2349 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2624    0.9563    2.1696 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1196   -1.1146   -1.7341 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
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 14 16  2  0
 16 17  1  0
 16 18  1  0
  8 19  2  0
 19 20  1  0
  4 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  1  0
 23 25  2  0
 25 26  1  0
 25 27  1  0
 27  2  1  0
 19  3  1  0
 27 21  1  0
 18  9  1  0
 18 12  1  0
  5 28  1  0
  7 29  1  0
  9 30  1  6
 10 31  1  0
 10 32  1  0
 11 33  1  0
 11 34  1  0
 13 35  1  0
 20 36  1  0
 22 37  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Not Available

Chemical Formula

C₁₈H₁₀Cl₄N₂O₃

Average Mass

444.0900 Da

Monoisotopic Mass

441.94455 Da

IUPAC Name

2,3-dichloro-7-[(3S)-5,6-dichloro-2,3-dihydro-1H-pyrrolizin-3-yl]-6,8-dihydroxy-5H-benzo[a]pyrrolizin-5-one

Traditional Name

2,3-dichloro-7-[(3S)-5,6-dichloro-2,3-dihydro-1H-pyrrolizin-3-yl]-6,8-dihydroxybenzo[a]pyrrolizin-5-one

CAS Registry Number

Not Available

SMILES

OC1=C([C@@H]2CCC3=CC(Cl)=C(Cl)N23)C(O)=C2C(=O)N3C(Cl)=C(Cl)C=C3C2=C1

InChI Identifier

InChI=1S/C18H10Cl4N2O3/c19-8-3-6-1-2-10(23(6)16(8)21)14-12(25)4-7-11-5-9(20)17(22)24(11)18(27)13(7)15(14)26/h3-5,10,25-26H,1-2H2/t10-/m0/s1

InChI Key

PNWJMZXCEYWQFJ-JTQLQIEISA-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 sp.	NPAtlas	23405849

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as isoindolones. These are aromatic polycyclic compounds that an isoindole bearing a ketone.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Isoindoles and derivatives

Sub Class

Isoindolines

Direct Parent

Isoindolones

Alternative Parents

Substituents

Isoindolone
Pyrrolizine
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Aryl chloride
Aryl halide
Substituted pyrrole
Benzenoid
Pyrrole
Heteroaromatic compound
Vinylogous acid
Lactam
Azacycle
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Organochloride
Organohalogen compound
Organic oxide
Organic nitrogen compound
Organic oxygen compound
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	5.47	ALOGPS
logP	4.4	ChemAxon
logS	-4.4	ALOGPS
pKa (Strongest Acidic)	7.93	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	67.39 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	104.78 m³·mol⁻¹	ChemAxon
Polarizability	41.6 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

NPA008760

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

28945556

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

71583130

PDB ID

Not Available

ChEBI ID

156431

Good Scents ID

Not Available

References

General References

Alvarez-Mico X, Jensen PR, Fenical W, Hughes CC: Chlorizidine, a cytotoxic 5H-pyrrolo[2,1-a]isoindol-5-one-containing alkaloid from a marine Streptomyces sp. Org Lett. 2013 Mar 1;15(5):988-91. doi: 10.1021/ol303374e. Epub 2013 Feb 13. [PubMed:23405849 ]

Showing NP-Card for Chlorizidine A (NP0011496)

MOL for NP0011496 (Chlorizidine A)

3D MOL for NP0011496 (Chlorizidine A)

3D SDF for NP0011496 (Chlorizidine A)

3D-SDF for NP0011496 (Chlorizidine A)

PDB for NP0011496 (Chlorizidine A)

3D PDB for NP0011496 (Chlorizidine A)

SMILES for NP0011496 (Chlorizidine A)

INCHI for NP0011496 (Chlorizidine A)

Structure for NP0011496 (Chlorizidine A)

3D Structure for NP0011496 (Chlorizidine A)