NP-MRD: Showing NP-Card for Psychrophilin A (NP0005357)

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Record Information

Version

2.0

Created at

2020-12-09 02:37:30 UTC

Updated at

2021-07-15 16:51:46 UTC

NP-MRD ID

NP0005357

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Psychrophilin A

Provided By

NPAtlas

Description

(11S,17S)-10-hydroxy-17-nitro-1,9,15-triazapentacyclo[17.6.1.0³,⁸.0¹¹,¹⁵.0²⁰,²⁵]Hexacosa-3,5,7,9,19(26),20,22,24-octaene-2,16-dione belongs to the class of organic compounds known as dipeptides. These are organic compounds containing a sequence of exactly two alpha-amino acids joined by a peptide bond. Psychrophilin A is found in Penicillium. Psychrophilin A was first documented in 2004 (PMID: 15165155). Based on a literature review very few articles have been published on (11S,17S)-10-hydroxy-17-nitro-1,9,15-triazapentacyclo[17.6.1.0³,⁸.0¹¹,¹⁵.0²⁰,²⁵]Hexacosa-3,5,7,9,19(26),20,22,24-octaene-2,16-dione.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242118183D          

 52 56  0  0  0  0            999 V2000
    2.4006    0.3095   -1.6958 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4444    0.8283   -0.9446 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6834    1.8738   -1.4586 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2237    2.8715   -1.0030 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3236    4.1954   -0.9893 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3131    5.3171   -0.5903 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6082    5.1890   -0.1562 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1660    3.9518   -0.1563 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5223    2.7563   -0.5703 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3529    1.5372   -0.5256 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6369    1.8317   -0.4853 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0084    0.1464   -0.5146 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2835   -0.5839   -1.3704 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1780   -1.8544   -0.8696 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8867   -1.9089    0.3532 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1232   -2.9513    1.2688 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8817   -2.6982    2.3857 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3895   -1.4441    2.5848 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1722   -0.4087    1.7050 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3947   -0.6639    0.5589 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3911   -3.0299   -1.3367 C   0  0  2  0  0  0  0  0  0  0  0  0
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    2.4932   -4.0230   -2.8550 O   0  0  0  0  0  0  0  0  0  0  0  0
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    1.6827   -2.4096   -0.0639 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7674   -3.3902    0.7953 O   0  0  0  0  0  0  0  0  0  0  0  0
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    3.5312   -0.9105    0.8687 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5968    0.5899    1.0473 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1788    0.9967    1.3280 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4284    0.1145    0.3435 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8460    2.0193   -2.5479 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.1936    6.0393    0.1850 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.7126   -3.3835   -2.3085 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5011   -3.9414   -0.6763 H   0  0  0  0  0  0  0  0  0  0  0  0
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    1.8896    0.8083    2.3736 H   0  0  0  0  0  0  0  0  0  0  0  0
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    0.4163   -0.0971    0.7443 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
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  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
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 26 27  2  0  0  0  0
 26 28  1  0  0  0  0
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 31 32  1  0  0  0  0
 32  2  1  0  0  0  0
  9  4  1  0  0  0  0
 20 12  1  0  0  0  0
 32 28  1  0  0  0  0
 20 15  1  0  0  0  0
  3 33  1  0  0  0  0
  5 34  1  0  0  0  0
  6 35  1  0  0  0  0
  7 36  1  0  0  0  0
  8 37  1  0  0  0  0
 13 38  1  0  0  0  0
 16 39  1  0  0  0  0
 17 40  1  0  0  0  0
 18 41  1  0  0  0  0
 19 42  1  0  0  0  0
 21 43  1  0  0  0  0
 21 44  1  0  0  0  0
 22 45  1  6  0  0  0
 29 46  1  0  0  0  0
 29 47  1  0  0  0  0
 30 48  1  0  0  0  0
 30 49  1  0  0  0  0
 31 50  1  0  0  0  0
 31 51  1  0  0  0  0
 32 52  1  1  0  0  0
M  CHG  2  23   1  25  -1
M  END

     RDKit          3D

 52 56  0  0  0  0  0  0  0  0999 V2000
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    1.4444    0.8283   -0.9446 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.2237    2.8715   -1.0030 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3236    4.1954   -0.9893 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.1660    3.9518   -0.1563 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.0084    0.1464   -0.5146 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2835   -0.5839   -1.3704 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1780   -1.8544   -0.8696 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8867   -1.9089    0.3532 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.8817   -2.6982    2.3857 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3895   -1.4441    2.5848 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1722   -0.4087    1.7050 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3947   -0.6639    0.5589 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3911   -3.0299   -1.3367 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0893   -2.8025   -1.3541 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7774   -4.0149   -1.8465 N   0  0  0  0  0  4  0  0  0  0  0  0
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   -0.5011   -3.9414   -0.6763 H   0  0  0  0  0  0  0  0  0  0  0  0
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    4.3282   -1.3050    0.2632 H   0  0  0  0  0  0  0  0  0  0  0  0
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    0.4163   -0.0971    0.7443 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
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  5  6  1  0
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 29 30  1  0
 30 31  1  0
 31 32  1  0
 32  2  1  0
  9  4  1  0
 20 12  1  0
 32 28  1  0
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  3 33  1  0
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 29 46  1  0
 29 47  1  0
 30 48  1  0
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 31 50  1  0
 31 51  1  0
 32 52  1  1
M  CHG  2  23   1  25  -1
M  END


  Mrv1652306242118183D          

 52 56  0  0  0  0            999 V2000
    2.4006    0.3095   -1.6958 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4444    0.8283   -0.9446 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6834    1.8738   -1.4586 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2237    2.8715   -1.0030 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3236    4.1954   -0.9893 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.5312   -0.9105    0.8687 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5968    0.5899    1.0473 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1788    0.9967    1.3280 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4284    0.1145    0.3435 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8460    2.0193   -2.5479 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.7105   -3.9398    1.0903 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.9863   -1.2447    3.4628 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5814    0.5721    1.8795 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7126   -3.3835   -2.3085 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5011   -3.9414   -0.6763 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2797   -2.0539   -2.1443 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6168   -1.3780    1.8844 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3282   -1.3050    0.2632 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1961    0.8430    1.9671 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0472    1.1169    0.2032 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8896    0.8083    2.3736 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0287    2.0386    1.0220 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4163   -0.0971    0.7443 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  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 14 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 23 25  1  0  0  0  0
 22 26  1  0  0  0  0
 26 27  2  0  0  0  0
 26 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32  2  1  0  0  0  0
  9  4  1  0  0  0  0
 20 12  1  0  0  0  0
 32 28  1  0  0  0  0
 20 15  1  0  0  0  0
  3 33  1  0  0  0  0
  5 34  1  0  0  0  0
  6 35  1  0  0  0  0
  7 36  1  0  0  0  0
  8 37  1  0  0  0  0
 13 38  1  0  0  0  0
 16 39  1  0  0  0  0
 17 40  1  0  0  0  0
 18 41  1  0  0  0  0
 19 42  1  0  0  0  0
 21 43  1  0  0  0  0
 21 44  1  0  0  0  0
 22 45  1  6  0  0  0
 29 46  1  0  0  0  0
 29 47  1  0  0  0  0
 30 48  1  0  0  0  0
 30 49  1  0  0  0  0
 31 50  1  0  0  0  0
 31 51  1  0  0  0  0
 32 52  1  1  0  0  0
M  CHG  2  23   1  25  -1
M  END
> <DATABASE_ID>
NP0005357

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]N1C2=C([H])C([H])=C([H])C([H])=C2C(=O)N2C([H])=C(C3=C([H])C([H])=C([H])C([H])=C23)C([H])([H])[C@@]([H])(C(=O)N2C([H])([H])C([H])([H])C([H])([H])[C@@]2([H])C1=O)[N+]([O-])=O

> <INCHI_IDENTIFIER>
InChI=1S/C23H20N4O5/c28-21-19-10-5-11-25(19)23(30)20(27(31)32)12-14-13-26(18-9-4-2-6-15(14)18)22(29)16-7-1-3-8-17(16)24-21/h1-4,6-9,13,19-20H,5,10-12H2,(H,24,28)/t19-,20-/m0/s1

> <INCHI_KEY>
YQOXDTHSLKEXLH-PMACEKPBSA-N

> <FORMULA>
C23H20N4O5

> <MOLECULAR_WEIGHT>
432.436

> <EXACT_MASS>
432.14336976

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
52

> <JCHEM_AVERAGE_POLARIZABILITY>
43.21177078629091

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
{[(11S,17S)-2,10,16-trioxo-1,9,15-triazapentacyclo[17.6.1.0^{3,8}.0^{11,15}.0^{20,25}]hexacosa-3,5,7,19(26),20,22,24-heptaen-17-yl]nitro}-lambda1-oxidanyl

> <ALOGPS_LOGP>
2.54

> <JCHEM_LOGP>
2.2018567640000004

> <ALOGPS_LOGS>
-4.11

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
11.938924305073504

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.932052226308904

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9033529294206

> <JCHEM_POLAR_SURFACE_AREA>
114.55

> <JCHEM_REFRACTIVITY>
115.01399999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.35e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[(11S,17S)-2,10,16-trioxo-1,9,15-triazapentacyclo[17.6.1.0^{3,8}.0^{11,15}.0^{20,25}]hexacosa-3,5,7,19(26),20,22,24-heptaen-17-ylnitro]-lambda1-oxidanyl

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 52 56  0  0  0  0  0  0  0  0999 V2000
    2.4006    0.3095   -1.6958 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4444    0.8283   -0.9446 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6834    1.8738   -1.4586 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2237    2.8715   -1.0030 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3236    4.1954   -0.9893 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3131    5.3171   -0.5903 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6082    5.1890   -0.1562 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1660    3.9518   -0.1563 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5223    2.7563   -0.5703 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3529    1.5372   -0.5256 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6369    1.8317   -0.4853 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0084    0.1464   -0.5146 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2835   -0.5839   -1.3704 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1780   -1.8544   -0.8696 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8867   -1.9089    0.3532 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1232   -2.9513    1.2688 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8817   -2.6982    2.3857 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3895   -1.4441    2.5848 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1722   -0.4087    1.7050 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3947   -0.6639    0.5589 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3911   -3.0299   -1.3367 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0893   -2.8025   -1.3541 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7774   -4.0149   -1.8465 N   0  0  0  0  0  4  0  0  0  0  0  0
    2.4932   -4.0230   -2.8550 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6084   -5.1807   -1.1455 O   0  0  0  0  0  1  0  0  0  0  0  0
    1.6827   -2.4096   -0.0639 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7674   -3.3902    0.7953 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1631   -1.1319    0.3458 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5312   -0.9105    0.8687 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5968    0.5899    1.0473 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1788    0.9967    1.3280 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4284    0.1145    0.3435 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8460    2.0193   -2.5479 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3531    4.3549   -1.3690 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1442    6.3016   -0.5957 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1936    6.0393    0.1850 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2047    3.8807    0.2054 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8379   -0.2100   -2.3795 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7105   -3.9398    1.0903 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0545   -3.5238    3.0870 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9863   -1.2447    3.4628 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5814    0.5721    1.8795 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7126   -3.3835   -2.3085 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5011   -3.9414   -0.6763 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2797   -2.0539   -2.1443 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6168   -1.3780    1.8844 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3282   -1.3050    0.2632 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1961    0.8430    1.9671 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0472    1.1169    0.2032 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8896    0.8083    2.3736 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0287    2.0386    1.0220 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4163   -0.0971    0.7443 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 14 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  2  0
 23 25  1  0
 22 26  1  0
 26 27  2  0
 26 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  1  0
 31 32  1  0
 32  2  1  0
  9  4  1  0
 20 12  1  0
 32 28  1  0
 20 15  1  0
  3 33  1  0
  5 34  1  0
  6 35  1  0
  7 36  1  0
  8 37  1  0
 13 38  1  0
 16 39  1  0
 17 40  1  0
 18 41  1  0
 19 42  1  0
 21 43  1  0
 21 44  1  0
 22 45  1  6
 29 46  1  0
 29 47  1  0
 30 48  1  0
 30 49  1  0
 31 50  1  0
 31 51  1  0
 32 52  1  1
M  CHG  2  23   1  25  -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  O   UNK     0       2.401   0.310  -1.696  0.00  0.00           O+0
HETATM    2  C   UNK     0       1.444   0.828  -0.945  0.00  0.00           C+0
HETATM    3  N   UNK     0       0.683   1.874  -1.459  0.00  0.00           N+0
HETATM    4  C   UNK     0      -0.224   2.872  -1.003  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.324   4.195  -0.989  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.313   5.317  -0.590  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.608   5.189  -0.156  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.166   3.952  -0.156  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.522   2.756  -0.570  0.00  0.00           C+0
HETATM   10  C   UNK     0      -2.353   1.537  -0.526  0.00  0.00           C+0
HETATM   11  O   UNK     0      -3.637   1.832  -0.485  0.00  0.00           O+0
HETATM   12  N   UNK     0      -2.008   0.146  -0.515  0.00  0.00           N+0
HETATM   13  C   UNK     0      -1.284  -0.584  -1.370  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.178  -1.854  -0.870  0.00  0.00           C+0
HETATM   15  C   UNK     0      -1.887  -1.909   0.353  0.00  0.00           C+0
HETATM   16  C   UNK     0      -2.123  -2.951   1.269  0.00  0.00           C+0
HETATM   17  C   UNK     0      -2.882  -2.698   2.386  0.00  0.00           C+0
HETATM   18  C   UNK     0      -3.389  -1.444   2.585  0.00  0.00           C+0
HETATM   19  C   UNK     0      -3.172  -0.409   1.705  0.00  0.00           C+0
HETATM   20  C   UNK     0      -2.395  -0.664   0.559  0.00  0.00           C+0
HETATM   21  C   UNK     0      -0.391  -3.030  -1.337  0.00  0.00           C+0
HETATM   22  C   UNK     0       1.089  -2.803  -1.354  0.00  0.00           C+0
HETATM   23  N   UNK     0       1.777  -4.015  -1.847  0.00  0.00           N+1
HETATM   24  O   UNK     0       2.493  -4.023  -2.855  0.00  0.00           O+0
HETATM   25  O   UNK     0       1.608  -5.181  -1.145  0.00  0.00           O-1
HETATM   26  C   UNK     0       1.683  -2.410  -0.064  0.00  0.00           C+0
HETATM   27  O   UNK     0       1.767  -3.390   0.795  0.00  0.00           O+0
HETATM   28  N   UNK     0       2.163  -1.132   0.346  0.00  0.00           N+0
HETATM   29  C   UNK     0       3.531  -0.911   0.869  0.00  0.00           C+0
HETATM   30  C   UNK     0       3.597   0.590   1.047  0.00  0.00           C+0
HETATM   31  C   UNK     0       2.179   0.997   1.328  0.00  0.00           C+0
HETATM   32  C   UNK     0       1.428   0.115   0.344  0.00  0.00           C+0
HETATM   33  H   UNK     0       0.846   2.019  -2.548  0.00  0.00           H+0
HETATM   34  H   UNK     0       1.353   4.355  -1.369  0.00  0.00           H+0
HETATM   35  H   UNK     0       0.144   6.302  -0.596  0.00  0.00           H+0
HETATM   36  H   UNK     0      -2.194   6.039   0.185  0.00  0.00           H+0
HETATM   37  H   UNK     0      -3.205   3.881   0.205  0.00  0.00           H+0
HETATM   38  H   UNK     0      -0.838  -0.210  -2.380  0.00  0.00           H+0
HETATM   39  H   UNK     0      -1.710  -3.940   1.090  0.00  0.00           H+0
HETATM   40  H   UNK     0      -3.054  -3.524   3.087  0.00  0.00           H+0
HETATM   41  H   UNK     0      -3.986  -1.245   3.463  0.00  0.00           H+0
HETATM   42  H   UNK     0      -3.581   0.572   1.880  0.00  0.00           H+0
HETATM   43  H   UNK     0      -0.713  -3.384  -2.309  0.00  0.00           H+0
HETATM   44  H   UNK     0      -0.501  -3.941  -0.676  0.00  0.00           H+0
HETATM   45  H   UNK     0       1.280  -2.054  -2.144  0.00  0.00           H+0
HETATM   46  H   UNK     0       3.617  -1.378   1.884  0.00  0.00           H+0
HETATM   47  H   UNK     0       4.328  -1.305   0.263  0.00  0.00           H+0
HETATM   48  H   UNK     0       4.196   0.843   1.967  0.00  0.00           H+0
HETATM   49  H   UNK     0       4.047   1.117   0.203  0.00  0.00           H+0
HETATM   50  H   UNK     0       1.890   0.808   2.374  0.00  0.00           H+0
HETATM   51  H   UNK     0       2.029   2.039   1.022  0.00  0.00           H+0
HETATM   52  H   UNK     0       0.416  -0.097   0.744  0.00  0.00           H+0
CONECT    1    2                                                            
CONECT    2    1    3   32                                                  
CONECT    3    2    4   33                                                  
CONECT    4    3    5    9                                                  
CONECT    5    4    6   34                                                  
CONECT    6    5    7   35                                                  
CONECT    7    6    8   36                                                  
CONECT    8    7    9   37                                                  
CONECT    9    8   10    4                                                  
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13   20                                                  
CONECT   13   12   14   38                                                  
CONECT   14   13   15   21                                                  
CONECT   15   14   16   20                                                  
CONECT   16   15   17   39                                                  
CONECT   17   16   18   40                                                  
CONECT   18   17   19   41                                                  
CONECT   19   18   20   42                                                  
CONECT   20   19   12   15                                                  
CONECT   21   14   22   43   44                                             
CONECT   22   21   23   26   45                                             
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23                                                            
CONECT   26   22   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   29   32                                                  
CONECT   29   28   30   46   47                                             
CONECT   30   29   31   48   49                                             
CONECT   31   30   32   50   51                                             
CONECT   32   31    2   28   52                                             
CONECT   33    3                                                            
CONECT   34    5                                                            
CONECT   35    6                                                            
CONECT   36    7                                                            
CONECT   37    8                                                            
CONECT   38   13                                                            
CONECT   39   16                                                            
CONECT   40   17                                                            
CONECT   41   18                                                            
CONECT   42   19                                                            
CONECT   43   21                                                            
CONECT   44   21                                                            
CONECT   45   22                                                            
CONECT   46   29                                                            
CONECT   47   29                                                            
CONECT   48   30                                                            
CONECT   49   30                                                            
CONECT   50   31                                                            
CONECT   51   31                                                            
CONECT   52   32                                                            
MASTER        0    0    0    0    0    0    0    0   52    0  112    0
END

RDKit          3D

52 56  0  0  0  0  0  0  0  0999 V2000
    2.4006    0.3095   -1.6958 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4444    0.8283   -0.9446 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6834    1.8738   -1.4586 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2237    2.8715   -1.0030 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3236    4.1954   -0.9893 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3131    5.3171   -0.5903 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6082    5.1890   -0.1562 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1660    3.9518   -0.1563 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5223    2.7563   -0.5703 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3529    1.5372   -0.5256 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6369    1.8317   -0.4853 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0084    0.1464   -0.5146 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2835   -0.5839   -1.3704 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1780   -1.8544   -0.8696 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8867   -1.9089    0.3532 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1232   -2.9513    1.2688 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8817   -2.6982    2.3857 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3895   -1.4441    2.5848 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1722   -0.4087    1.7050 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3947   -0.6639    0.5589 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3911   -3.0299   -1.3367 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0893   -2.8025   -1.3541 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7774   -4.0149   -1.8465 N   0  0  0  0  0  4  0  0  0  0  0  0
    2.4932   -4.0230   -2.8550 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6084   -5.1807   -1.1455 O   0  0  0  0  0  1  0  0  0  0  0  0
    1.6827   -2.4096   -0.0639 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7674   -3.3902    0.7953 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1631   -1.1319    0.3458 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5312   -0.9105    0.8687 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5968    0.5899    1.0473 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1788    0.9967    1.3280 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4284    0.1145    0.3435 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8460    2.0193   -2.5479 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3531    4.3549   -1.3690 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1442    6.3016   -0.5957 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1936    6.0393    0.1850 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2047    3.8807    0.2054 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8379   -0.2100   -2.3795 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7105   -3.9398    1.0903 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0545   -3.5238    3.0870 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9863   -1.2447    3.4628 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5814    0.5721    1.8795 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7126   -3.3835   -2.3085 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5011   -3.9414   -0.6763 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2797   -2.0539   -2.1443 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6168   -1.3780    1.8844 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3282   -1.3050    0.2632 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1961    0.8430    1.9671 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0472    1.1169    0.2032 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8896    0.8083    2.3736 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0287    2.0386    1.0220 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4163   -0.0971    0.7443 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 14 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  2  0
 23 25  1  0
 22 26  1  0
 26 27  2  0
 26 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  1  0
 31 32  1  0
 32  2  1  0
  9  4  1  0
 20 12  1  0
 32 28  1  0
 20 15  1  0
  3 33  1  0
  5 34  1  0
  6 35  1  0
  7 36  1  0
  8 37  1  0
 13 38  1  0
 16 39  1  0
 17 40  1  0
 18 41  1  0
 19 42  1  0
 21 43  1  0
 21 44  1  0
 22 45  1  6
 29 46  1  0
 29 47  1  0
 30 48  1  0
 30 49  1  0
 31 50  1  0
 31 51  1  0
 32 52  1  1
M  CHG  2  23   1  25  -1
M  END

View in JSmol View NMR Assignments

Synonyms

Not Available

Chemical Formula

C₂₃H₂₀N₄O₅

Average Mass

432.4360 Da

Monoisotopic Mass

432.14337 Da

IUPAC Name

{[(11S,17S)-2,10,16-trioxo-1,9,15-triazapentacyclo[17.6.1.0^{3,8}.0^{11,15}.0^{20,25}]hexacosa-3,5,7,19(26),20,22,24-heptaen-17-yl]nitro}-lambda1-oxidanyl

Traditional Name

[(11S,17S)-2,10,16-trioxo-1,9,15-triazapentacyclo[17.6.1.0^{3,8}.0^{11,15}.0^{20,25}]hexacosa-3,5,7,19(26),20,22,24-heptaen-17-ylnitro]-lambda1-oxidanyl

CAS Registry Number

Not Available

SMILES

[O-][N+](=O)[C@H]1CC2=CN(C3=CC=CC=C23)C(=O)C2=CC=CC=C2NC(=O)[C@@H]2CCCN2C1=O

InChI Identifier

InChI=1S/C23H20N4O5/c28-21-19-10-5-11-25(19)23(30)20(27(31)32)12-14-13-26(18-9-4-2-6-15(14)18)22(29)16-7-1-3-8-17(16)24-21/h1-4,6-9,13,19-20H,5,10-12H2,(H,24,28)/t19-,20-/m0/s1

InChI Key

YQOXDTHSLKEXLH-PMACEKPBSA-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	NPAtlas	15165155

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as dipeptides. These are organic compounds containing a sequence of exactly two alpha-amino acids joined by a peptide bond.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Dipeptides

Alternative Parents

Substituents

Alpha-dipeptide
Macrolactam
Alpha-amino acid or derivatives
3-alkylindole
Indole
Indole or derivatives
Benzenoid
Heteroaromatic compound
Pyrrole
Pyrrolidine
Tertiary carboxylic acid amide
Vinylogous amide
Carboxamide group
Lactam
C-nitro compound
Organic nitro compound
Secondary carboxylic acid amide
Organoheterocyclic compound
Azacycle
Organic oxoazanium
Organic 1,3-dipolar compound
Allyl-type 1,3-dipolar organic compound
Propargyl-type 1,3-dipolar organic compound
Organic oxygen compound
Organic nitrogen compound
Organooxygen compound
Organonitrogen compound
Carbonyl group
Hydrocarbon derivative
Organic oxide
Organic salt
Organic zwitterion
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	2.54	ALOGPS
logP	2.2	ChemAxon
logS	-4.1	ALOGPS
pKa (Strongest Acidic)	4.93	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	114.55 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	115.01 m³·mol⁻¹	ChemAxon
Polarizability	43.21 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

NPA017049

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

10190610

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

21578956

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Dalsgaard PW, Larsen TO, Frydenvang K, Christophersen C: Psychrophilin A and cycloaspeptide D, novel cyclic peptides from the psychrotolerant fungus Penicillium ribeum. J Nat Prod. 2004 May;67(5):878-81. doi: 10.1021/np0303714. [PubMed:15165155 ]

Showing NP-Card for Psychrophilin A (NP0005357)

MOL for NP0005357 (Psychrophilin A)

3D MOL for NP0005357 (Psychrophilin A)

3D SDF for NP0005357 (Psychrophilin A)

3D-SDF for NP0005357 (Psychrophilin A)

PDB for NP0005357 (Psychrophilin A)

3D PDB for NP0005357 (Psychrophilin A)

SMILES for NP0005357 (Psychrophilin A)

INCHI for NP0005357 (Psychrophilin A)

Structure for NP0005357 (Psychrophilin A)

3D Structure for NP0005357 (Psychrophilin A)