NP-MRD: Showing NP-Card for Citrinalin B (NP0009551)

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Record Information

Version

2.0

Created at

2021-01-05 19:08:23 UTC

Updated at

2021-07-15 17:03:35 UTC

NP-MRD ID

NP0009551

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Citrinalin B

Provided By

NPAtlas

Description

Citrinalin B is found in Penicillium citrinum. Based on a literature review very few articles have been published on CHEMBL1739034.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242106363D          

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M  END

     RDKit          3D

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M  CHG  2  19   1  21  -1
M  END


  Mrv1652306242106363D          

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   -2.3845    0.2191    0.1629 C   0  0  1  0  0  0  0  0  0  0  0  0
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   -2.1263    1.3978    2.2358 O   0  5  0  0  0  1  0  0  0  0  0  0
   -3.8081    0.7272   -0.0419 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.6839   -0.2494    0.4384 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7180    0.1009    1.2990 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.8790   -1.1187    2.1953 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.1109   -2.2280    1.5198 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.4846   -1.5920    0.2754 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.0862   -2.1162    0.0511 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.3179   -1.0503   -0.6031 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9159   -1.3112   -0.9758 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9080   -1.7915   -2.4428 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1717   -2.3394   -0.2160 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9141    0.7934    0.9512 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6152    2.8386    1.9951 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0758    3.8440    0.6272 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8680    3.0493    1.7662 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3813    0.7861    1.4611 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8900    1.9157    0.1880 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2901    0.2242   -0.2595 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2489    3.1792   -1.1133 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3033    1.8351   -1.7152 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9139   -0.0901    2.5091 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6200   -0.4263    1.7265 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9207    1.2120   -3.2626 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8565    1.5920   -1.3578 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9012    1.8225    0.1600 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9287    1.6668    0.5330 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9601    0.9604   -1.1046 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6869    0.3088    0.7780 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4640    1.0100    1.8734 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9315   -1.3853    2.3566 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4417   -0.8356    3.1749 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2606   -2.4951    2.2080 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7289   -3.1018    1.2654 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1129   -1.9662   -0.5861 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6461   -2.5945    0.9449 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1469   -2.9756   -0.6959 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8981   -0.8321   -1.5672 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8244   -1.4445   -2.9610 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0174   -2.8942   -2.3826 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0289   -1.5724   -2.9456 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2041   -3.3432   -0.7479 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9391   -2.1347   -0.1935 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5636   -2.5968    0.7862 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 16 14  1  6  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  1  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
 18 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
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  6  0  0  0
 30 32  1  0  0  0  0
  8 33  1  0  0  0  0
 33  2  1  0  0  0  0
 12  7  1  0  0  0  0
 30 16  1  0  0  0  0
 16 11  1  0  0  0  0
 29 18  1  0  0  0  0
 27 23  1  0  0  0  0
  1 34  1  0  0  0  0
  1 35  1  0  0  0  0
  1 36  1  0  0  0  0
  3 37  1  0  0  0  0
  3 38  1  0  0  0  0
  3 39  1  0  0  0  0
  4 40  1  0  0  0  0
  4 41  1  0  0  0  0
  9 42  1  0  0  0  0
 10 43  1  0  0  0  0
 13 44  1  0  0  0  0
 17 45  1  0  0  0  0
 17 46  1  0  0  0  0
 22 47  1  0  0  0  0
 22 48  1  0  0  0  0
 24 49  1  0  0  0  0
 24 50  1  0  0  0  0
 25 51  1  0  0  0  0
 25 52  1  0  0  0  0
 26 53  1  0  0  0  0
 26 54  1  0  0  0  0
 27 55  1  6  0  0  0
 28 56  1  0  0  0  0
 28 57  1  0  0  0  0
 29 58  1  6  0  0  0
 31 59  1  0  0  0  0
 31 60  1  0  0  0  0
 31 61  1  0  0  0  0
 32 62  1  0  0  0  0
 32 63  1  0  0  0  0
 32 64  1  0  0  0  0
M  CHG  2  19   1  21  -1
M  END
> <DATABASE_ID>
NP0009551

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]N1C(=O)[C@@]2(C3=C1C1=C(OC(C([H])([H])[H])(C([H])([H])[H])C([H])([H])C1=O)C([H])=C3[H])C([H])([H])[C@@]1([N+]([O-])=O)C([H])([H])N3C([H])([H])C([H])([H])C([H])([H])[C@]3([H])C([H])([H])[C@]1([H])C2(C([H])([H])[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C25H31N3O5/c1-22(2)11-16(29)19-17(33-22)8-7-15-20(19)26-21(30)25(15)12-24(28(31)32)13-27-9-5-6-14(27)10-18(24)23(25,3)4/h7-8,14,18H,5-6,9-13H2,1-4H3,(H,26,30)/t14-,18-,24-,25+/m1/s1

> <INCHI_KEY>
QVBARITWSQCBBV-KUCRYEJDSA-N

> <FORMULA>
C25H31N3O5

> <MOLECULAR_WEIGHT>
453.539

> <EXACT_MASS>
453.22637111

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
64

> <JCHEM_AVERAGE_POLARIZABILITY>
48.453526439459026

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
{[(5aS,7S,8aR,9aR)-7',7',8,8-tetramethyl-2',9'-dioxo-1,2,2',3,5,5a,6,7',8,8',8a,9,9',9a-tetradecahydro-1'H-spiro[cyclopenta[f]indolizine-7,3'-pyrano[2,3-g]indole]-5a-yl]nitro}-lambda1-oxidanyl

> <ALOGPS_LOGP>
3.83

> <JCHEM_LOGP>
3.329109016666667

> <ALOGPS_LOGS>
-3.99

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
14.776397290865486

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.945809772117558

> <JCHEM_PKA_STRONGEST_BASIC>
8.266479911688949

> <JCHEM_POLAR_SURFACE_AREA>
101.78

> <JCHEM_REFRACTIVITY>
121.99869999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.60e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[(5aS,7S,8aR,9aR)-7',7',8,8-tetramethyl-2',9'-dioxo-1,1',2,3,5,6,8',8a,9,9a-decahydrospiro[cyclopenta[f]indolizine-7,3'-pyrano[2,3-g]indole]-5a-ylnitro]-lambda1-oxidanyl

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 64 69  0  0  0  0  0  0  0  0999 V2000
    5.8298    2.9421    1.2229 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7845    1.6903    0.3362 C   0  0  2  0  0  0  0  0  0  0  0  0
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    5.4264    2.0840   -1.0522 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.2342    0.8375   -0.7153 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6089    0.5811    0.5894 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6662    0.1241    1.4767 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3737   -0.0670    1.0447 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9504    0.1788   -0.2634 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9136    0.6346   -1.1267 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3691    0.8554   -2.4167 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0080    0.5237   -2.3559 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7830    0.6063   -3.3106 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3167    0.0694   -0.9921 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3567    1.0512   -0.4992 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3845    0.2191    0.1629 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1660    0.2079    1.5539 N   0  0  0  0  0  4  0  0  0  0  0  0
   -2.0174   -0.8127    2.2152 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1263    1.3978    2.2358 O   0  0  0  0  0  1  0  0  0  0  0  0
   -3.8081    0.7272   -0.0419 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6839   -0.2494    0.4384 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7180    0.1009    1.2990 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8790   -1.1187    2.1953 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1109   -2.2280    1.5198 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4846   -1.5920    0.2754 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.0862   -2.1162    0.0511 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3179   -1.0503   -0.6031 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9159   -1.3112   -0.9758 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9080   -1.7915   -2.4428 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1717   -2.3394   -0.2160 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9141    0.7934    0.9512 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6152    2.8386    1.9951 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0758    3.8440    0.6272 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8680    3.0493    1.7662 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3813    0.7861    1.4611 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8900    1.9157    0.1880 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2901    0.2242   -0.2595 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2489    3.1792   -1.1133 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3033    1.8351   -1.7152 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9139   -0.0901    2.5091 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6200   -0.4263    1.7265 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9207    1.2120   -3.2626 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8565    1.5920   -1.3578 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9012    1.8225    0.1600 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9287    1.6668    0.5330 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9601    0.9604   -1.1046 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6869    0.3088    0.7780 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4640    1.0100    1.8734 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9315   -1.3853    2.3566 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4417   -0.8356    3.1749 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2606   -2.4951    2.2080 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7289   -3.1018    1.2654 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1129   -1.9662   -0.5861 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6461   -2.5945    0.9449 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1469   -2.9756   -0.6959 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8981   -0.8321   -1.5672 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8244   -1.4445   -2.9610 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0174   -2.8942   -2.3826 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0289   -1.5724   -2.9456 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2041   -3.3432   -0.7479 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9391   -2.1347   -0.1935 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5636   -2.5968    0.7862 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 16 14  1  6
 16 17  1  0
 17 18  1  0
 18 19  1  1
 19 20  2  0
 19 21  1  0
 18 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  1  6
 30 32  1  0
  8 33  1  0
 33  2  1  0
 12  7  1  0
 30 16  1  0
 16 11  1  0
 29 18  1  0
 27 23  1  0
  1 34  1  0
  1 35  1  0
  1 36  1  0
  3 37  1  0
  3 38  1  0
  3 39  1  0
  4 40  1  0
  4 41  1  0
  9 42  1  0
 10 43  1  0
 13 44  1  0
 17 45  1  0
 17 46  1  0
 22 47  1  0
 22 48  1  0
 24 49  1  0
 24 50  1  0
 25 51  1  0
 25 52  1  0
 26 53  1  0
 26 54  1  0
 27 55  1  6
 28 56  1  0
 28 57  1  0
 29 58  1  6
 31 59  1  0
 31 60  1  0
 31 61  1  0
 32 62  1  0
 32 63  1  0
 32 64  1  0
M  CHG  2  19   1  21  -1
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  C   UNK     0       5.830   2.942   1.223  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.785   1.690   0.336  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.186   1.090   0.421  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.426   2.084  -1.052  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.272   1.319  -1.614  0.00  0.00           C+0
HETATM    6  O   UNK     0       4.176   1.086  -2.825  0.00  0.00           O+0
HETATM    7  C   UNK     0       3.234   0.838  -0.715  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.609   0.581   0.589  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.666   0.124   1.477  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.374  -0.067   1.045  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.950   0.179  -0.263  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.914   0.635  -1.127  0.00  0.00           C+0
HETATM   13  N   UNK     0       1.369   0.855  -2.417  0.00  0.00           N+0
HETATM   14  C   UNK     0       0.008   0.524  -2.356  0.00  0.00           C+0
HETATM   15  O   UNK     0      -0.783   0.606  -3.311  0.00  0.00           O+0
HETATM   16  C   UNK     0      -0.317   0.069  -0.992  0.00  0.00           C+0
HETATM   17  C   UNK     0      -1.357   1.051  -0.499  0.00  0.00           C+0
HETATM   18  C   UNK     0      -2.385   0.219   0.163  0.00  0.00           C+0
HETATM   19  N   UNK     0      -2.166   0.208   1.554  0.00  0.00           N+1
HETATM   20  O   UNK     0      -2.017  -0.813   2.215  0.00  0.00           O+0
HETATM   21  O   UNK     0      -2.126   1.398   2.236  0.00  0.00           O-1
HETATM   22  C   UNK     0      -3.808   0.727  -0.042  0.00  0.00           C+0
HETATM   23  N   UNK     0      -4.684  -0.249   0.438  0.00  0.00           N+0
HETATM   24  C   UNK     0      -5.718   0.101   1.299  0.00  0.00           C+0
HETATM   25  C   UNK     0      -5.879  -1.119   2.195  0.00  0.00           C+0
HETATM   26  C   UNK     0      -5.111  -2.228   1.520  0.00  0.00           C+0
HETATM   27  C   UNK     0      -4.485  -1.592   0.275  0.00  0.00           C+0
HETATM   28  C   UNK     0      -3.086  -2.116   0.051  0.00  0.00           C+0
HETATM   29  C   UNK     0      -2.318  -1.050  -0.603  0.00  0.00           C+0
HETATM   30  C   UNK     0      -0.916  -1.311  -0.976  0.00  0.00           C+0
HETATM   31  C   UNK     0      -0.908  -1.792  -2.443  0.00  0.00           C+0
HETATM   32  C   UNK     0      -0.172  -2.339  -0.216  0.00  0.00           C+0
HETATM   33  O   UNK     0       4.914   0.793   0.951  0.00  0.00           O+0
HETATM   34  H   UNK     0       6.615   2.839   1.995  0.00  0.00           H+0
HETATM   35  H   UNK     0       6.076   3.844   0.627  0.00  0.00           H+0
HETATM   36  H   UNK     0       4.868   3.049   1.766  0.00  0.00           H+0
HETATM   37  H   UNK     0       7.381   0.786   1.461  0.00  0.00           H+0
HETATM   38  H   UNK     0       7.890   1.916   0.188  0.00  0.00           H+0
HETATM   39  H   UNK     0       7.290   0.224  -0.260  0.00  0.00           H+0
HETATM   40  H   UNK     0       5.249   3.179  -1.113  0.00  0.00           H+0
HETATM   41  H   UNK     0       6.303   1.835  -1.715  0.00  0.00           H+0
HETATM   42  H   UNK     0       2.914  -0.090   2.509  0.00  0.00           H+0
HETATM   43  H   UNK     0       0.620  -0.426   1.726  0.00  0.00           H+0
HETATM   44  H   UNK     0       1.921   1.212  -3.263  0.00  0.00           H+0
HETATM   45  H   UNK     0      -1.857   1.592  -1.358  0.00  0.00           H+0
HETATM   46  H   UNK     0      -0.901   1.823   0.160  0.00  0.00           H+0
HETATM   47  H   UNK     0      -3.929   1.667   0.533  0.00  0.00           H+0
HETATM   48  H   UNK     0      -3.960   0.960  -1.105  0.00  0.00           H+0
HETATM   49  H   UNK     0      -6.687   0.309   0.778  0.00  0.00           H+0
HETATM   50  H   UNK     0      -5.464   1.010   1.873  0.00  0.00           H+0
HETATM   51  H   UNK     0      -6.931  -1.385   2.357  0.00  0.00           H+0
HETATM   52  H   UNK     0      -5.442  -0.836   3.175  0.00  0.00           H+0
HETATM   53  H   UNK     0      -4.261  -2.495   2.208  0.00  0.00           H+0
HETATM   54  H   UNK     0      -5.729  -3.102   1.265  0.00  0.00           H+0
HETATM   55  H   UNK     0      -5.113  -1.966  -0.586  0.00  0.00           H+0
HETATM   56  H   UNK     0      -2.646  -2.595   0.945  0.00  0.00           H+0
HETATM   57  H   UNK     0      -3.147  -2.976  -0.696  0.00  0.00           H+0
HETATM   58  H   UNK     0      -2.898  -0.832  -1.567  0.00  0.00           H+0
HETATM   59  H   UNK     0      -1.824  -1.444  -2.961  0.00  0.00           H+0
HETATM   60  H   UNK     0      -1.017  -2.894  -2.383  0.00  0.00           H+0
HETATM   61  H   UNK     0       0.029  -1.572  -2.946  0.00  0.00           H+0
HETATM   62  H   UNK     0      -0.204  -3.343  -0.748  0.00  0.00           H+0
HETATM   63  H   UNK     0       0.939  -2.135  -0.194  0.00  0.00           H+0
HETATM   64  H   UNK     0      -0.564  -2.597   0.786  0.00  0.00           H+0
CONECT    1    2   34   35   36                                             
CONECT    2    1    3    4   33                                             
CONECT    3    2   37   38   39                                             
CONECT    4    2    5   40   41                                             
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8   12                                                  
CONECT    8    7    9   33                                                  
CONECT    9    8   10   42                                                  
CONECT   10    9   11   43                                                  
CONECT   11   10   12   16                                                  
CONECT   12   11   13    7                                                  
CONECT   13   12   14   44                                                  
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17   30   11                                             
CONECT   17   16   18   45   46                                             
CONECT   18   17   19   22   29                                             
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19                                                            
CONECT   22   18   23   47   48                                             
CONECT   23   22   24   27                                                  
CONECT   24   23   25   49   50                                             
CONECT   25   24   26   51   52                                             
CONECT   26   25   27   53   54                                             
CONECT   27   26   28   23   55                                             
CONECT   28   27   29   56   57                                             
CONECT   29   28   30   18   58                                             
CONECT   30   29   31   32   16                                             
CONECT   31   30   59   60   61                                             
CONECT   32   30   62   63   64                                             
CONECT   33    8    2                                                       
CONECT   34    1                                                            
CONECT   35    1                                                            
CONECT   36    1                                                            
CONECT   37    3                                                            
CONECT   38    3                                                            
CONECT   39    3                                                            
CONECT   40    4                                                            
CONECT   41    4                                                            
CONECT   42    9                                                            
CONECT   43   10                                                            
CONECT   44   13                                                            
CONECT   45   17                                                            
CONECT   46   17                                                            
CONECT   47   22                                                            
CONECT   48   22                                                            
CONECT   49   24                                                            
CONECT   50   24                                                            
CONECT   51   25                                                            
CONECT   52   25                                                            
CONECT   53   26                                                            
CONECT   54   26                                                            
CONECT   55   27                                                            
CONECT   56   28                                                            
CONECT   57   28                                                            
CONECT   58   29                                                            
CONECT   59   31                                                            
CONECT   60   31                                                            
CONECT   61   31                                                            
CONECT   62   32                                                            
CONECT   63   32                                                            
CONECT   64   32                                                            
MASTER        0    0    0    0    0    0    0    0   64    0  138    0
END

RDKit          3D

64 69  0  0  0  0  0  0  0  0999 V2000
    5.8298    2.9421    1.2229 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7845    1.6903    0.3362 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.1858    1.0901    0.4213 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4264    2.0840   -1.0522 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2720    1.3195   -1.6136 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1765    1.0858   -2.8245 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2342    0.8375   -0.7153 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6089    0.5811    0.5894 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6662    0.1241    1.4767 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3737   -0.0670    1.0447 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9504    0.1788   -0.2634 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9136    0.6346   -1.1267 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3691    0.8554   -2.4167 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0080    0.5237   -2.3559 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7830    0.6063   -3.3106 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3167    0.0694   -0.9921 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3567    1.0512   -0.4992 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3845    0.2191    0.1629 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1660    0.2079    1.5539 N   0  0  0  0  0  4  0  0  0  0  0  0
   -2.0174   -0.8127    2.2152 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1263    1.3978    2.2358 O   0  0  0  0  0  1  0  0  0  0  0  0
   -3.8081    0.7272   -0.0419 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6839   -0.2494    0.4384 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7180    0.1009    1.2990 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8790   -1.1187    2.1953 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1109   -2.2280    1.5198 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4846   -1.5920    0.2754 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.0862   -2.1162    0.0511 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3179   -1.0503   -0.6031 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9159   -1.3112   -0.9758 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9080   -1.7915   -2.4428 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1717   -2.3394   -0.2160 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9141    0.7934    0.9512 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6152    2.8386    1.9951 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0758    3.8440    0.6272 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8680    3.0493    1.7662 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3813    0.7861    1.4611 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8900    1.9157    0.1880 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2901    0.2242   -0.2595 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2489    3.1792   -1.1133 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3033    1.8351   -1.7152 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9139   -0.0901    2.5091 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6200   -0.4263    1.7265 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9207    1.2120   -3.2626 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8565    1.5920   -1.3578 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9012    1.8225    0.1600 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9287    1.6668    0.5330 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9601    0.9604   -1.1046 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6869    0.3088    0.7780 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4640    1.0100    1.8734 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9315   -1.3853    2.3566 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4417   -0.8356    3.1749 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2606   -2.4951    2.2080 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7289   -3.1018    1.2654 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1129   -1.9662   -0.5861 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6461   -2.5945    0.9449 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1469   -2.9756   -0.6959 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8981   -0.8321   -1.5672 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8244   -1.4445   -2.9610 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0174   -2.8942   -2.3826 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0289   -1.5724   -2.9456 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2041   -3.3432   -0.7479 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9391   -2.1347   -0.1935 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5636   -2.5968    0.7862 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 16 14  1  6
 16 17  1  0
 17 18  1  0
 18 19  1  1
 19 20  2  0
 19 21  1  0
 18 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  1  6
 30 32  1  0
  8 33  1  0
 33  2  1  0
 12  7  1  0
 30 16  1  0
 16 11  1  0
 29 18  1  0
 27 23  1  0
  1 34  1  0
  1 35  1  0
  1 36  1  0
  3 37  1  0
  3 38  1  0
  3 39  1  0
  4 40  1  0
  4 41  1  0
  9 42  1  0
 10 43  1  0
 13 44  1  0
 17 45  1  0
 17 46  1  0
 22 47  1  0
 22 48  1  0
 24 49  1  0
 24 50  1  0
 25 51  1  0
 25 52  1  0
 26 53  1  0
 26 54  1  0
 27 55  1  6
 28 56  1  0
 28 57  1  0
 29 58  1  6
 31 59  1  0
 31 60  1  0
 31 61  1  0
 32 62  1  0
 32 63  1  0
 32 64  1  0
M  CHG  2  19   1  21  -1
M  END

View in JSmol View NMR Assignments

Synonyms

Not Available

Chemical Formula

C₂₅H₃₁N₃O₅

Average Mass

453.5390 Da

Monoisotopic Mass

453.22637 Da

IUPAC Name

{[(5aS,7S,8aR,9aR)-7',7',8,8-tetramethyl-2',9'-dioxo-1,2,2',3,5,5a,6,7',8,8',8a,9,9',9a-tetradecahydro-1'H-spiro[cyclopenta[f]indolizine-7,3'-pyrano[2,3-g]indole]-5a-yl]nitro}-lambda1-oxidanyl

Traditional Name

[(5aS,7S,8aR,9aR)-7',7',8,8-tetramethyl-2',9'-dioxo-1,1',2,3,5,6,8',8a,9,9a-decahydrospiro[cyclopenta[f]indolizine-7,3'-pyrano[2,3-g]indole]-5a-ylnitro]-lambda1-oxidanyl

CAS Registry Number

Not Available

SMILES

CC1(C)[C@H]2C[C@H]3CCCN3C[C@@]2(C[C@]11C(=O)NC2=C1C=CC1=C2C(=O)CC(C)(C)O1)[N+]([O-])=O

InChI Identifier

InChI=1S/C25H31N3O5/c1-22(2)11-16(29)19-17(33-22)8-7-15-20(19)26-21(30)25(15)12-24(28(31)32)13-27-9-5-6-14(27)10-18(24)23(25,3)4/h7-8,14,18H,5-6,9-13H2,1-4H3,(H,26,30)/t14-,18-,24-,25+/m1/s1

InChI Key

QVBARITWSQCBBV-KUCRYEJDSA-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
Penicillium citrinum	NPAtlas	21053938

Chemical Taxonomy

Classification

Not classified

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	3.83	ALOGPS
logP	3.33	ChemAxon
logS	-4	ALOGPS
pKa (Strongest Acidic)	11.95	ChemAxon
pKa (Strongest Basic)	8.27	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	101.78 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	122 m³·mol⁻¹	ChemAxon
Polarizability	48.45 Å³	ChemAxon
Number of Rings	6	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

NPA014353

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

26338883

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

50900042

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for Citrinalin B (NP0009551)

MOL for NP0009551 (Citrinalin B)

3D MOL for NP0009551 (Citrinalin B)

3D SDF for NP0009551 (Citrinalin B)

3D-SDF for NP0009551 (Citrinalin B)

PDB for NP0009551 (Citrinalin B)

3D PDB for NP0009551 (Citrinalin B)

SMILES for NP0009551 (Citrinalin B)

INCHI for NP0009551 (Citrinalin B)

Structure for NP0009551 (Citrinalin B)

3D Structure for NP0009551 (Citrinalin B)