NP-MRD: Showing NP-Card for (2s,3s,4s,5r,6r)-3-{[(2r)-1,3-dihydroxy-2-{[1-hydroxy-2-(methylamino)ethylidene]amino}propylidene]amino}-4,5-dihydroxy-6-(2-hydroxy-4-iminopyrimidin-1-yl)oxane-2-carboximidic acid (NP0142441)

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Record Information

Version

2.0

Created at

2022-09-01 20:59:21 UTC

Updated at

2022-09-01 20:59:21 UTC

NP-MRD ID

NP0142441

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2s,3s,4s,5r,6r)-3-{[(2r)-1,3-dihydroxy-2-{[1-hydroxy-2-(methylamino)ethylidene]amino}propylidene]amino}-4,5-dihydroxy-6-(2-hydroxy-4-iminopyrimidin-1-yl)oxane-2-carboximidic acid

Description

Gougerotin, also known as aspiculamycin or asteromycin, belongs to the class of organic compounds known as hybrid glycopeptides. Hybrid glycopeptides are compounds containing a carbohydrate component linked to a hybrid peptide component. (2s,3s,4s,5r,6r)-3-{[(2r)-1,3-dihydroxy-2-{[1-hydroxy-2-(methylamino)ethylidene]amino}propylidene]amino}-4,5-dihydroxy-6-(2-hydroxy-4-iminopyrimidin-1-yl)oxane-2-carboximidic acid is found in Streptomyces hygroscopicus. (2s,3s,4s,5r,6r)-3-{[(2r)-1,3-dihydroxy-2-{[1-hydroxy-2-(methylamino)ethylidene]amino}propylidene]amino}-4,5-dihydroxy-6-(2-hydroxy-4-iminopyrimidin-1-yl)oxane-2-carboximidic acid was first documented in 2013 (PMID: 24121866). Based on a literature review a small amount of articles have been published on Gougerotin (PMID: 27382784) (PMID: 24242236) (PMID: 23515837) (PMID: 23352137).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309012222592D          

 31 32  0  0  1  0            999 V2000
   -2.1434    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    3.3000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7145   -3.7125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -6.1875    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000   -4.9500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7145   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  4  0  0  0
  4  6  2  0  0  0  0
  7  6  1  6  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  7 10  1  0  0  0  0
 10 11  1  4  0  0  0
 10 12  2  0  0  0  0
 13 12  1  6  0  0  0
 13 14  1  0  0  0  0
 14 15  1  1  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
 14 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  1  0  0  0
 20 21  1  0  0  0  0
 21 22  2  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
 25 26  2  0  0  0  0
 20 26  1  0  0  0  0
 26 27  1  0  0  0  0
 19 28  1  0  0  0  0
 28 29  1  6  0  0  0
 28 30  1  0  0  0  0
 13 30  1  0  0  0  0
 30 31  1  1  0  0  0
M  END

     RDKit          3D

 56 57  0  0  0  0  0  0  0  0999 V2000
   -2.0464    2.9965    1.2222 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7192    2.0921    0.8400 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7967    1.0050    1.5267 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3364    1.0886    2.8018 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3187   -0.2965    0.9587 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.2892   -1.2390    1.0765 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9319   -1.6545   -0.0542 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.0617   -0.7795   -0.2631 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2929    0.0047   -1.2940 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4172    0.8130   -1.4007 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3363    0.7970   -0.3824 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3931    1.5332   -0.4453 N   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0840    1.5014    0.3525 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0859   -0.0169    0.6770 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9901   -0.7800    0.7402 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8299   -1.5829    1.8791 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0984   -1.9567   -1.2312 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.9810   -3.3521   -1.4701 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6467   -1.5160   -0.9922 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1080   -1.5930   -2.1260 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7764   -0.1149   -0.4359 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4635    0.6194   -0.4054 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6288    0.1480   -0.2652 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7950   -1.2210   -0.1198 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8696    0.9643   -0.2429 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5902    2.4224   -0.5081 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8436    2.9948    0.5231 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6033    0.8320    0.9707 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.8773    0.9051    1.0634 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5091    0.7589    2.3206 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8136    1.1388   -0.0642 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6963   -0.0290   -0.1771 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.8784   -1.1479   -0.6193 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9498    1.6844    3.5380 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4590   -0.6119    1.5849 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4198   -2.6417    0.2448 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6032    0.0422   -2.0951 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5795    1.4454   -2.2592 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7637   -1.1648    2.8101 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3836   -1.5372   -2.1917 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8798   -3.7852   -1.4054 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3032   -2.2147   -0.1735 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0231   -2.4918   -2.5221 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4592    0.4914   -1.0748 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3979   -1.6244    0.6069 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4876    0.5876   -1.0814 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5597    2.9341   -0.6449 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9803    2.4836   -1.4300 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4921    2.3238    1.1606 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6870   -0.1402    2.7161 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3386    1.3728   -1.0102 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5074    1.9662    0.2715 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1642   -0.2207    0.7292 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3676   -2.1222   -0.4278 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6953   -0.9860   -1.7124 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9013   -1.1267   -0.0886 H   0  0  0  0  0  0  0  0  0  0  0  0
 33 32  1  0
 32 31  1  0
 31 29  1  0
 29 30  1  0
 29 28  2  0
 28 25  1  0
 25 26  1  0
 26 27  1  0
 25 23  1  0
 23 24  1  0
 23 22  2  0
 22 21  1  0
 21 19  1  0
 19 20  1  0
 19 17  1  0
 17 18  1  0
 17  7  1  0
  7  6  1  0
  6  5  1  0
  5  3  1  0
  3  4  1  0
  3  2  2  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 11 14  1  0
 14 15  2  0
 15 16  1  0
  5 21  1  0
 15  8  1  0
 33 54  1  0
 33 55  1  0
 33 56  1  0
 32 53  1  0
 31 51  1  0
 31 52  1  0
 30 50  1  0
 25 46  1  6
 26 47  1  0
 26 48  1  0
 27 49  1  0
 24 45  1  0
 21 44  1  6
 19 42  1  1
 20 43  1  0
 17 40  1  6
 18 41  1  0
  7 36  1  1
  5 35  1  1
  4 34  1  0
  2  1  1  0
  9 37  1  0
 10 38  1  0
 12 13  1  0
 16 39  1  0
M  END


  Mrv1652309012222592D          

 31 32  0  0  1  0            999 V2000
   -2.1434    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    3.3000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7145   -3.7125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -6.1875    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000   -4.9500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7145   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  4  0  0  0
  4  6  2  0  0  0  0
  7  6  1  6  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  7 10  1  0  0  0  0
 10 11  1  4  0  0  0
 10 12  2  0  0  0  0
 13 12  1  6  0  0  0
 13 14  1  0  0  0  0
 14 15  1  1  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
 14 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  1  0  0  0
 20 21  1  0  0  0  0
 21 22  2  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
 25 26  2  0  0  0  0
 20 26  1  0  0  0  0
 26 27  1  0  0  0  0
 19 28  1  0  0  0  0
 28 29  1  6  0  0  0
 28 30  1  0  0  0  0
 13 30  1  0  0  0  0
 30 31  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0142441

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CNCC(O)=N[C@H](CO)C(O)=N[C@H]1[C@H](O)[C@@H](O)[C@@H](O[C@@H]1C(O)=N)N1C=CC(=N)N=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C16H25N7O8/c1-19-4-8(25)20-6(5-24)14(29)22-9-10(26)11(27)15(31-12(9)13(18)28)23-3-2-7(17)21-16(23)30/h2-3,6,9-12,15,19,24,26-27H,4-5H2,1H3,(H2,18,28)(H,20,25)(H,22,29)(H2,17,21,30)/t6-,9+,10+,11-,12+,15-/m1/s1

> <INCHI_KEY>
AMNAZJFEONUVTD-QJHHURCWSA-N

> <FORMULA>
C16H25N7O8

> <MOLECULAR_WEIGHT>
443.417

> <EXACT_MASS>
443.176460793

> <JCHEM_ACCEPTOR_COUNT>
15

> <JCHEM_ATOM_COUNT>
56

> <JCHEM_AVERAGE_POLARIZABILITY>
42.59312641642599

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
10

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S,3S,4S,5R,6R)-3-[(1,3-dihydroxy-2-{[1-hydroxy-2-(methylamino)ethylidene]amino}propylidene)amino]-4,5-dihydroxy-6-(2-hydroxy-4-imino-1,4-dihydropyrimidin-1-yl)oxane-2-carboximidic acid

> <ALOGPS_LOGP>
-1.72

> <JCHEM_LOGP>
-8.282709367657205

> <ALOGPS_LOGS>
-3.67

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
2.966266980904965

> <JCHEM_PKA_STRONGEST_ACIDIC>
-3.576147142216417

> <JCHEM_PKA_STRONGEST_BASIC>
12.045741437031412

> <JCHEM_POLAR_SURFACE_AREA>
250.88999999999993

> <JCHEM_REFRACTIVITY>
123.6661

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
9.40e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S,3S,4S,5R,6R)-3-[(1,3-dihydroxy-2-{[1-hydroxy-2-(methylamino)ethylidene]amino}propylidene)amino]-4,5-dihydroxy-6-(2-hydroxy-4-iminopyrimidin-1-yl)oxane-2-carboximidic acid

> <JCHEM_VEBER_RULE>
0

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HEADER    PROTEIN                                 01-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   01-SEP-22         0                                  
HETATM    1  C   UNK     0      -4.001   6.930   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0      -2.667   6.160   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0      -2.667   4.620   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       0.000   4.620   0.000  0.00  0.00           O+0
HETATM    6  N   UNK     0      -1.334   2.310   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       2.667   1.540   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -1.334  -0.770   0.000  0.00  0.00           O+0
HETATM   12  N   UNK     0       1.334  -0.770   0.000  0.00  0.00           N+0
HETATM   13  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   16  N   UNK     0       5.335  -3.080   0.000  0.00  0.00           N+0
HETATM   17  O   UNK     0       4.001  -0.770   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   20  N   UNK     0       1.334  -6.930   0.000  0.00  0.00           N+0
HETATM   21  C   UNK     0       2.667  -7.700   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       2.667  -9.240   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       1.334 -10.010   0.000  0.00  0.00           C+0
HETATM   24  N   UNK     0       1.334 -11.550   0.000  0.00  0.00           N+0
HETATM   25  N   UNK     0      -0.000  -9.240   0.000  0.00  0.00           N+0
HETATM   26  C   UNK     0       0.000  -7.700   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      -1.334  -6.930   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      -1.334  -5.390   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      -1.334  -2.310   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6    8   10                                                  
CONECT    8    7    9                                                       
CONECT    9    8                                                            
CONECT   10    7   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12   14   30                                                  
CONECT   14   13   15   18                                                  
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15                                                            
CONECT   18   14   19                                                       
CONECT   19   18   20   28                                                  
CONECT   20   19   21   26                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26                                                       
CONECT   26   25   20   27                                                  
CONECT   27   26                                                            
CONECT   28   19   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   13   31                                                  
CONECT   31   30                                                            
MASTER        0    0    0    0    0    0    0    0   31    0   64    0
END

View in JSmol

Synonyms

Value	Source
Aspiculamycin	MeSH
Asteromycin	MeSH

Chemical Formula

C₁₆H₂₅N₇O₈

Average Mass

443.4170 Da

Monoisotopic Mass

443.17646 Da

IUPAC Name

(2S,3S,4S,5R,6R)-3-[(1,3-dihydroxy-2-{[1-hydroxy-2-(methylamino)ethylidene]amino}propylidene)amino]-4,5-dihydroxy-6-(2-hydroxy-4-imino-1,4-dihydropyrimidin-1-yl)oxane-2-carboximidic acid

Traditional Name

(2S,3S,4S,5R,6R)-3-[(1,3-dihydroxy-2-{[1-hydroxy-2-(methylamino)ethylidene]amino}propylidene)amino]-4,5-dihydroxy-6-(2-hydroxy-4-iminopyrimidin-1-yl)oxane-2-carboximidic acid

CAS Registry Number

Not Available

SMILES

CNCC(O)=N[C@H](CO)C(O)=N[C@H]1[C@H](O)[C@@H](O)[C@@H](O[C@@H]1C(O)=N)N1C=CC(=N)N=C1O

InChI Identifier

InChI=1S/C16H25N7O8/c1-19-4-8(25)20-6(5-24)14(29)22-9-10(26)11(27)15(31-12(9)13(18)28)23-3-2-7(17)21-16(23)30/h2-3,6,9-12,15,19,24,26-27H,4-5H2,1H3,(H2,18,28)(H,20,25)(H,22,29)(H2,17,21,30)/t6-,9+,10+,11-,12+,15-/m1/s1

InChI Key

AMNAZJFEONUVTD-QJHHURCWSA-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, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, 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 hygroscopicus	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as hybrid glycopeptides. Hybrid glycopeptides are compounds containing a carbohydrate component linked to a hybrid peptide component.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Peptidomimetics

Sub Class

Hybrid peptides

Direct Parent

Hybrid glycopeptides

Alternative Parents

Substituents

Hybrid glycopeptide
Alpha-dipeptide
N-acyl-alpha amino acid or derivatives
Alpha-amino acid amide
Serine or derivatives
N-glycosyl compound
Glycosyl compound
N-substituted-alpha-amino acid
Alpha-amino acid or derivatives
Pyrimidone
Aminopyrimidine
Oxane
Imidolactam
Pyrimidine
Pyran
Hydropyrimidine
Heteroaromatic compound
Carboxamide group
Secondary carboxylic acid amide
Secondary alcohol
Primary carboxylic acid amide
Amino acid or derivatives
Oxacycle
Carboxylic acid derivative
Secondary aliphatic amine
Azacycle
Organoheterocyclic compound
Secondary amine
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Alcohol
Carbonyl group
Hydrocarbon derivative
Amine
Organic oxide
Primary amine
Primary alcohol
Organonitrogen compound
Organooxygen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic 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	-1.7	ALOGPS
logP	-8.3	ChemAxon
logS	-3.7	ALOGPS
pKa (Strongest Acidic)	-3.6	ChemAxon
pKa (Strongest Basic)	12.05	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	15	ChemAxon
Hydrogen Donor Count	10	ChemAxon
Polar Surface Area	250.89 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	123.67 m³·mol⁻¹	ChemAxon
Polarizability	42.59 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	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

C00018700

Chemspider ID

9401772

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Gougerotin

METLIN ID

Not Available

PubChem Compound

11226719

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Wei J, Zhang J, Jiang L, Tan H, Niu G: [Functional characterization of gouC and gouD in gougerotin biosynthesis]. Wei Sheng Wu Xue Bao. 2016 Mar 4;56(3):406-17. [PubMed:27382784 ]
Wei J, Tian Y, Niu G, Tan H: GouR, a TetR family transcriptional regulator, coordinates the biosynthesis and export of gougerotin in Streptomyces graminearus. Appl Environ Microbiol. 2014 Jan;80(2):714-22. doi: 10.1128/AEM.03003-13. Epub 2013 Nov 15. [PubMed:24242236 ]
Jiang L, Wei J, Li L, Niu G, Tan H: Combined gene cluster engineering and precursor feeding to improve gougerotin production in Streptomyces graminearus. Appl Microbiol Biotechnol. 2013 Dec;97(24):10469-77. doi: 10.1007/s00253-013-5270-6. [PubMed:24121866 ]
Du D, Zhu Y, Wei J, Tian Y, Niu G, Tan H: Improvement of gougerotin and nikkomycin production by engineering their biosynthetic gene clusters. Appl Microbiol Biotechnol. 2013 Jul;97(14):6383-96. doi: 10.1007/s00253-013-4836-7. Epub 2013 Mar 21. [PubMed:23515837 ]
Niu G, Li L, Wei J, Tan H: Cloning, heterologous expression, and characterization of the gene cluster required for gougerotin biosynthesis. Chem Biol. 2013 Jan 24;20(1):34-44. doi: 10.1016/j.chembiol.2012.10.017. [PubMed:23352137 ]
LOTUS database [Link]

Showing NP-Card for (2s,3s,4s,5r,6r)-3-{[(2r)-1,3-dihydroxy-2-{[1-hydroxy-2-(methylamino)ethylidene]amino}propylidene]amino}-4,5-dihydroxy-6-(2-hydroxy-4-iminopyrimidin-1-yl)oxane-2-carboximidic acid (NP0142441)

MOL for NP0142441 ((2s,3s,4s,5r,6r)-3-{[(2r)-1,3-dihydroxy-2-{[1-hydroxy-2-(methylamino)ethylidene]amino}propylidene]amino}-4,5-dihydroxy-6-(2-hydroxy-4-iminopyrimidin-1-yl)oxane-2-carboximidic acid)

3D MOL for NP0142441 ((2s,3s,4s,5r,6r)-3-{[(2r)-1,3-dihydroxy-2-{[1-hydroxy-2-(methylamino)ethylidene]amino}propylidene]amino}-4,5-dihydroxy-6-(2-hydroxy-4-iminopyrimidin-1-yl)oxane-2-carboximidic acid)

3D SDF for NP0142441 ((2s,3s,4s,5r,6r)-3-{[(2r)-1,3-dihydroxy-2-{[1-hydroxy-2-(methylamino)ethylidene]amino}propylidene]amino}-4,5-dihydroxy-6-(2-hydroxy-4-iminopyrimidin-1-yl)oxane-2-carboximidic acid)

3D-SDF for NP0142441 ((2s,3s,4s,5r,6r)-3-{[(2r)-1,3-dihydroxy-2-{[1-hydroxy-2-(methylamino)ethylidene]amino}propylidene]amino}-4,5-dihydroxy-6-(2-hydroxy-4-iminopyrimidin-1-yl)oxane-2-carboximidic acid)

PDB for NP0142441 ((2s,3s,4s,5r,6r)-3-{[(2r)-1,3-dihydroxy-2-{[1-hydroxy-2-(methylamino)ethylidene]amino}propylidene]amino}-4,5-dihydroxy-6-(2-hydroxy-4-iminopyrimidin-1-yl)oxane-2-carboximidic acid)

3D PDB for NP0142441 ((2s,3s,4s,5r,6r)-3-{[(2r)-1,3-dihydroxy-2-{[1-hydroxy-2-(methylamino)ethylidene]amino}propylidene]amino}-4,5-dihydroxy-6-(2-hydroxy-4-iminopyrimidin-1-yl)oxane-2-carboximidic acid)

SMILES for NP0142441 ((2s,3s,4s,5r,6r)-3-{[(2r)-1,3-dihydroxy-2-{[1-hydroxy-2-(methylamino)ethylidene]amino}propylidene]amino}-4,5-dihydroxy-6-(2-hydroxy-4-iminopyrimidin-1-yl)oxane-2-carboximidic acid)

INCHI for NP0142441 ((2s,3s,4s,5r,6r)-3-{[(2r)-1,3-dihydroxy-2-{[1-hydroxy-2-(methylamino)ethylidene]amino}propylidene]amino}-4,5-dihydroxy-6-(2-hydroxy-4-iminopyrimidin-1-yl)oxane-2-carboximidic acid)

Structure for NP0142441 ((2s,3s,4s,5r,6r)-3-{[(2r)-1,3-dihydroxy-2-{[1-hydroxy-2-(methylamino)ethylidene]amino}propylidene]amino}-4,5-dihydroxy-6-(2-hydroxy-4-iminopyrimidin-1-yl)oxane-2-carboximidic acid)

3D Structure for NP0142441 ((2s,3s,4s,5r,6r)-3-{[(2r)-1,3-dihydroxy-2-{[1-hydroxy-2-(methylamino)ethylidene]amino}propylidene]amino}-4,5-dihydroxy-6-(2-hydroxy-4-iminopyrimidin-1-yl)oxane-2-carboximidic acid)