NP-MRD: Showing NP-Card for Holyrine A (NP0069945)

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Record Information

Version

2.0

Created at

2022-04-28 15:14:36 UTC

Updated at

2022-04-28 15:14:36 UTC

NP-MRD ID

NP0069945

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Holyrine A

Description

3-[(2R,4R,5S,6R)-4-amino-5-hydroxy-6-methyloxan-2-yl]-3,13,23-triazahexacyclo[14.7.0.0²,¹⁰.0⁴,⁹.0¹¹,¹⁵.0¹⁷,²²]Tricosa-1,4,6,8,10,12,15,17,19,21-decaen-12-ol belongs to the class of organic compounds known as indolocarbazoles. These are polycyclic aromatic compounds containing an indole fused to a carbazole. Holyrine A is found in Streptomyces sp. N96C-47. Based on a literature review very few articles have been published on 3-[(2R,4R,5S,6R)-4-amino-5-hydroxy-6-methyloxan-2-yl]-3,13,23-triazahexacyclo[14.7.0.0²,¹⁰.0⁴,⁹.0¹¹,¹⁵.0¹⁷,²²]Tricosa-1,4,6,8,10,12,15,17,19,21-decaen-12-ol.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282217142D          

 33 39  0  0  1  0            999 V2000
    6.2394    0.7481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1532   -0.0724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3995   -0.4080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7321    0.0769    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8183    0.8974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5720    1.2330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0647    1.2330    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5126    0.6199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9251   -0.0946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5126   -0.8091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6876   -0.8091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2751   -0.0946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6876    0.6199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1356    1.2330    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3819    0.8974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4681    0.0769    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8007   -0.4080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0470   -0.0724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0392    0.7481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6282    1.2330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4327   -1.5937    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1001   -2.0786    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7676   -1.5937    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5522   -1.8486    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8931    2.0400    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1085    2.2949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9370    3.1019    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5501    3.6539    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.3347    3.3990    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.5062    2.5920    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9478    3.9510    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3785    4.4609    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1524    3.3568    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  1  6  2  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  4  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
  8 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 12 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 15 20  2  0  0  0  0
 11 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 10 23  1  0  0  0  0
 23 24  2  0  0  0  0
 25  7  1  1  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
 25 30  1  0  0  0  0
 29 31  1  1  0  0  0
 28 32  1  6  0  0  0
 27 33  1  1  0  0  0
M  END

     RDKit          3D

 57 63  0  0  0  0  0  0  0  0999 V2000
    4.9821   -0.7604   -1.5302 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7971    0.1051   -1.1532 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8140   -0.7430   -0.6666 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6654   -0.0347   -0.2666 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5926   -0.9587   -0.0266 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6865   -2.2806    0.1906 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7938   -3.0915    0.2696 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7004   -4.4616    0.5104 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4657   -4.9965    0.6705 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6886   -4.2047    0.5980 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5748   -2.8584    0.3601 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4808   -1.8210    0.2394 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8594   -1.7745    0.3156 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4749   -0.5584    0.1536 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7649    0.5843   -0.0767 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1783    1.8960   -0.2572 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4225    2.4616   -0.2712 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5364    3.8371   -0.4800 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3921    4.5811   -0.6654 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1402    3.9670   -0.6444 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0194    2.6003   -0.4374 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9437    1.7560   -0.3700 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3929    0.5311   -0.1516 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7191   -0.6829    0.0051 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9512   -0.7171    0.2723 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1409   -2.1004    0.5008 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8626   -2.7756    0.5365 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7789   -3.9952    0.7299 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0833    0.7740    0.9219 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0711    1.8250    0.4083 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.3962    2.7821    1.4401 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2894    1.0470   -0.0463 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.2874    1.8544   -0.5298 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2091   -1.4122   -0.6395 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8808   -0.1584   -1.7765 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7263   -1.4174   -2.3847 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4731    0.7122   -2.0068 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4899    0.6469   -1.1324 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7764   -2.7043    0.1587 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5905   -5.0739    0.5667 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2983   -6.0679    0.8639 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6282   -4.6875    0.7332 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3445    1.9182   -0.1309 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5118    4.2941   -0.4930 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4631    5.6456   -0.8281 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2416    4.5305   -0.7868 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0166    2.1256   -0.4784 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2479   -0.0980    1.1570 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4850   -0.4193   -0.6521 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0685   -2.5579    0.6242 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6815    0.1181    1.5970 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2460    1.2354    1.4672 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6200    2.2887   -0.4870 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5599    2.9905    2.0334 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7273    3.6736    1.0131 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5949    0.4123    0.8025 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7970    2.2180    0.2296 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4 29  1  0
 29 30  1  0
 30 31  1  0
 30 32  1  0
 32 33  1  0
  4  5  1  0
  5  6  1  0
  6 11  1  0
 11 10  2  0
 10  9  1  0
  9  8  2  0
  8  7  1  0
 11 12  1  0
 12 24  2  0
 24 23  1  0
 23 15  2  0
 15 14  1  0
 14 13  2  0
 13 27  1  0
 27 28  2  0
 27 26  1  0
 26 25  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 32  2  1  0
 24  5  1  0
 22 23  1  0
  7  6  2  0
 13 12  1  0
 21 16  1  0
 25 14  1  0
  1 34  1  0
  1 35  1  0
  1 36  1  0
  2 37  1  6
  4 38  1  6
 29 51  1  0
 29 52  1  0
 30 53  1  6
 31 54  1  0
 31 55  1  0
 32 56  1  1
 33 57  1  0
 10 42  1  0
  9 41  1  0
  8 40  1  0
  7 39  1  0
 26 50  1  0
 25 48  1  0
 25 49  1  0
 17 43  1  0
 18 44  1  0
 19 45  1  0
 20 46  1  0
 22 47  1  0
M  END


  Mrv1652304282217142D          

 33 39  0  0  1  0            999 V2000
    6.2394    0.7481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1532   -0.0724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3995   -0.4080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7321    0.0769    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8183    0.8974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5720    1.2330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0647    1.2330    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5126    0.6199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9251   -0.0946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5126   -0.8091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6876   -0.8091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2751   -0.0946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6876    0.6199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1356    1.2330    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3819    0.8974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4681    0.0769    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8007   -0.4080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0470   -0.0724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0392    0.7481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6282    1.2330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4327   -1.5937    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1001   -2.0786    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7676   -1.5937    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5522   -1.8486    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8931    2.0400    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1085    2.2949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9370    3.1019    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5501    3.6539    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.3347    3.3990    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.5062    2.5920    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9478    3.9510    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3785    4.4609    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1524    3.3568    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  1  6  2  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  4  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
  8 13  1  0  0  0  0
 13 14  1  0  0  0  0
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 15 16  1  0  0  0  0
 12 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 15 20  2  0  0  0  0
 11 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 10 23  1  0  0  0  0
 23 24  2  0  0  0  0
 25  7  1  1  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
 25 30  1  0  0  0  0
 29 31  1  1  0  0  0
 28 32  1  6  0  0  0
 27 33  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0069945

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@H]1O[C@H](C[C@@H](N)[C@@H]1O)N1C2=C(C=CC=C2)C2=C1C1=C(C3=C2C(=O)NC3)C2=CC=CC=C2N1

> <INCHI_IDENTIFIER>
InChI=1S/C26H24N4O3/c1-12-25(31)16(27)10-19(33-12)30-18-9-5-3-7-14(18)21-22-15(11-28-26(22)32)20-13-6-2-4-8-17(13)29-23(20)24(21)30/h2-9,12,16,19,25,29,31H,10-11,27H2,1H3,(H,28,32)/t12-,16-,19-,25-/m1/s1

> <INCHI_KEY>
QNQXRLNOOGRQEB-DWPQWDBESA-N

> <FORMULA>
C26H24N4O3

> <MOLECULAR_WEIGHT>
440.503

> <EXACT_MASS>
440.184840649

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
57

> <JCHEM_AVERAGE_POLARIZABILITY>
47.323287556618006

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-[(2R,4R,5S,6R)-4-amino-5-hydroxy-6-methyloxan-2-yl]-3,13,23-triazahexacyclo[14.7.0.0^{2,10}.0^{4,9}.0^{11,15}.0^{17,22}]tricosa-1(16),2(10),4(9),5,7,11(15),17,19,21-nonaen-12-one

> <ALOGPS_LOGP>
1.97

> <JCHEM_LOGP>
2.684449373333333

> <ALOGPS_LOGS>
-4.23

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
13.780431644830415

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.15917249461928

> <JCHEM_PKA_STRONGEST_BASIC>
9.825027150987797

> <JCHEM_POLAR_SURFACE_AREA>
105.3

> <JCHEM_REFRACTIVITY>
124.57799999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.57e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-[(2R,4R,5S,6R)-4-amino-5-hydroxy-6-methyloxan-2-yl]-3,13,23-triazahexacyclo[14.7.0.0^{2,10}.0^{4,9}.0^{11,15}.0^{17,22}]tricosa-1(16),2(10),4(9),5,7,11(15),17,19,21-nonaen-12-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0      11.647   1.396   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      11.486  -0.135   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      10.079  -0.762   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.833   0.144   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.994   1.675   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      10.401   2.302   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0       7.587   2.302   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0       6.557   1.157   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.327  -0.177   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.557  -1.510   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.017  -1.510   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.247  -0.177   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.017   1.157   0.000  0.00  0.00           C+0
HETATM   14  N   UNK     0       3.986   2.302   0.000  0.00  0.00           N+0
HETATM   15  C   UNK     0       2.580   1.675   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.741   0.144   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.495  -0.762   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.088  -0.135   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -0.073   1.396   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.173   2.302   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.541  -2.975   0.000  0.00  0.00           C+0
HETATM   22  N   UNK     0       5.787  -3.880   0.000  0.00  0.00           N+0
HETATM   23  C   UNK     0       7.033  -2.975   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       8.497  -3.451   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       7.267   3.808   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       5.803   4.284   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       5.482   5.790   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       6.627   6.821   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       8.091   6.345   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       8.412   4.838   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       9.236   7.375   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       6.307   8.327   0.000  0.00  0.00           O+0
HETATM   33  N   UNK     0       4.018   6.266   0.000  0.00  0.00           N+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5    9                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5    1                                                       
CONECT    7    5    8   25                                                  
CONECT    8    7    9   13                                                  
CONECT    9    8    4   10                                                  
CONECT   10    9   11   23                                                  
CONECT   11   10   12   21                                                  
CONECT   12   11   13   16                                                  
CONECT   13   12    8   14                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   20                                                  
CONECT   16   15   12   17                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   15                                                       
CONECT   21   11   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   10   24                                                  
CONECT   24   23                                                            
CONECT   25    7   26   30                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28   33                                                  
CONECT   28   27   29   32                                                  
CONECT   29   28   30   31                                                  
CONECT   30   29   25                                                       
CONECT   31   29                                                            
CONECT   32   28                                                            
CONECT   33   27                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   78    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₆H₂₄N₄O₃

Average Mass

440.5030 Da

Monoisotopic Mass

440.18484 Da

IUPAC Name

3-[(2R,4R,5S,6R)-4-amino-5-hydroxy-6-methyloxan-2-yl]-3,13,23-triazahexacyclo[14.7.0.0^{2,10}.0^{4,9}.0^{11,15}.0^{17,22}]tricosa-1(16),2(10),4(9),5,7,11(15),17,19,21-nonaen-12-one

Traditional Name

3-[(2R,4R,5S,6R)-4-amino-5-hydroxy-6-methyloxan-2-yl]-3,13,23-triazahexacyclo[14.7.0.0^{2,10}.0^{4,9}.0^{11,15}.0^{17,22}]tricosa-1(16),2(10),4(9),5,7,11(15),17,19,21-nonaen-12-one

CAS Registry Number

Not Available

SMILES

C[C@H]1O[C@H](C[C@@H](N)[C@@H]1O)N1C2=C(C=CC=C2)C2=C1C1=C(C3=C2C(=O)NC3)C2=CC=CC=C2N1

InChI Identifier

InChI=1S/C26H24N4O3/c1-12-25(31)16(27)10-19(33-12)30-18-9-5-3-7-14(18)21-22-15(11-28-26(22)32)20-13-6-2-4-8-17(13)29-23(20)24(21)30/h2-9,12,16,19,25,29,31H,10-11,27H2,1H3,(H,28,32)/t12-,16-,19-,25-/m1/s1

InChI Key

QNQXRLNOOGRQEB-DWPQWDBESA-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. N96C-47	Bacteria	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as indolocarbazoles. These are polycyclic aromatic compounds containing an indole fused to a carbazole.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indoles and derivatives

Sub Class

Carbazoles

Direct Parent

Indolocarbazoles

Alternative Parents

Substituents

Indolocarbazole
Pyrrolo[2,3-a]carbazole
Pyrroloindole
N-alkylindole
Isoindole or derivatives
Isoindole
Indole
Benzenoid
Substituted pyrrole
Oxane
Heteroaromatic compound
Cyclic carboximidic acid
Pyrrole
Secondary alcohol
1,2-aminoalcohol
Oxacycle
Azacycle
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Hydrocarbon derivative
Primary amine
Organooxygen compound
Organonitrogen compound
Primary aliphatic amine
Amine
Alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	1.97	ALOGPS
logP	2.68	ChemAxon
logS	-4.2	ALOGPS
pKa (Strongest Acidic)	13.16	ChemAxon
pKa (Strongest Basic)	9.83	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	105.3 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	124.58 m³·mol⁻¹	ChemAxon
Polarizability	47.32 Å³	ChemAxon
Number of Rings	7	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

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

162972954

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for Holyrine A (NP0069945)

MOL for NP0069945 (Holyrine A)

3D MOL for NP0069945 (Holyrine A)

3D SDF for NP0069945 (Holyrine A)

3D-SDF for NP0069945 (Holyrine A)

PDB for NP0069945 (Holyrine A)

3D PDB for NP0069945 (Holyrine A)

SMILES for NP0069945 (Holyrine A)

INCHI for NP0069945 (Holyrine A)

Structure for NP0069945 (Holyrine A)

3D Structure for NP0069945 (Holyrine A)