NP-MRD: Showing NP-Card for {[(2r,3r,4r,6r)-3-hydroxy-6-{[(1r,5s,6r,8r,9e,11r,15e,17r)-1-hydroxy-5-[(2r,4r,5s,6s)-5-hydroxy-4,6-dimethyl-7-oxononan-2-yl]-6,8,16,18-tetramethyl-3-oxo-4,21-dioxabicyclo[15.3.1]henicosa-9,15,18-trien-11-yl]oxy}-2-methyloxan-4-yl]oxy}methanimidic acid (NP0195200)

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Record Information

Version

2.0

Created at

2022-09-04 13:01:00 UTC

Updated at

2022-09-04 13:01:00 UTC

NP-MRD ID

NP0195200

Secondary Accession Numbers

None

Natural Product Identification

Common Name

{[(2r,3r,4r,6r)-3-hydroxy-6-{[(1r,5s,6r,8r,9e,11r,15e,17r)-1-hydroxy-5-[(2r,4r,5s,6s)-5-hydroxy-4,6-dimethyl-7-oxononan-2-yl]-6,8,16,18-tetramethyl-3-oxo-4,21-dioxabicyclo[15.3.1]henicosa-9,15,18-trien-11-yl]oxy}-2-methyloxan-4-yl]oxy}methanimidic acid

Description

Venturicidin A belongs to the class of organic compounds known as diterpene lactones. These are diterpenoids containing a lactone moiety. {[(2r,3r,4r,6r)-3-hydroxy-6-{[(1r,5s,6r,8r,9e,11r,15e,17r)-1-hydroxy-5-[(2r,4r,5s,6s)-5-hydroxy-4,6-dimethyl-7-oxononan-2-yl]-6,8,16,18-tetramethyl-3-oxo-4,21-dioxabicyclo[15.3.1]henicosa-9,15,18-trien-11-yl]oxy}-2-methyloxan-4-yl]oxy}methanimidic acid is found in Streptomyces hygroscopicus. {[(2r,3r,4r,6r)-3-hydroxy-6-{[(1r,5s,6r,8r,9e,11r,15e,17r)-1-hydroxy-5-[(2r,4r,5s,6s)-5-hydroxy-4,6-dimethyl-7-oxononan-2-yl]-6,8,16,18-tetramethyl-3-oxo-4,21-dioxabicyclo[15.3.1]henicosa-9,15,18-trien-11-yl]oxy}-2-methyloxan-4-yl]oxy}methanimidic acid was first documented in 2005 (PMID: 15808937). Based on a literature review a significant number of articles have been published on Venturicidin A (PMID: 33356258) (PMID: 32424122) (PMID: 31450430) (PMID: 18667785) (PMID: 18481262).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309042215012D          

 53 55  0  0  1  0            999 V2000
   -5.0013   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -1.6500    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.8579   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -1.2375    0.0000 C   0  0  1  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   -1.6500    0.0000 C   0  0  2  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   -1.2375    0.0000 C   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
   -0.0000   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  1  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
   -0.0000    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
   -0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.0000    1.6500    0.0000 O   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
    1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 C   0  0  2  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
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.7158   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -2.4750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.4302   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -3.7125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.1447   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -5.3625    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -5.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -4.1250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.7158   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -3.7125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.2868   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 C   0  0  0  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
    1.4289   -1.6500    0.0000 C   0  0  1  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
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  6  0  0  0
  5  7  1  0  0  0  0
  7  8  1  1  0  0  0
  7  9  1  0  0  0  0
  9 10  1  1  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  6  0  0  0
 14 12  1  1  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  6  0  0  0
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 23 25  1  0  0  0  0
 25 26  1  1  0  0  0
 19 26  1  0  0  0  0
 25 27  1  0  0  0  0
 27 28  1  0  0  0  0
 27 29  2  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 33  1  0  0  0  0
 33 34  1  1  0  0  0
 35 34  1  1  0  0  0
 35 36  1  0  0  0  0
 36 37  1  0  0  0  0
 37 38  1  1  0  0  0
 38 39  1  0  0  0  0
 39 40  2  0  0  0  0
 39 41  1  0  0  0  0
 37 42  1  0  0  0  0
 42 43  1  6  0  0  0
 42 44  1  0  0  0  0
 44 45  1  1  0  0  0
 44 46  1  0  0  0  0
 35 46  1  0  0  0  0
 33 47  1  0  0  0  0
 47 48  2  0  0  0  0
 48 49  1  0  0  0  0
 49 50  1  6  0  0  0
 49 51  1  0  0  0  0
 51 52  1  0  0  0  0
 14 52  1  0  0  0  0
 52 53  1  1  0  0  0
M  END

     RDKit          3D

120122  0  0  0  0  0  0  0  0999 V2000
  -10.2515   -2.0191    2.3507 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.0300   -1.7368    1.7326 N   0  0  0  0  0  0  0  0  0  0  0  0
  -10.7899   -1.3122    0.5428 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.8711   -0.9433   -0.2552 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -8.5251   -2.1906    0.5138 C   0  0  2  0  0  0  0  0  0  0  0  0
   -7.2283   -1.7669   -0.1758 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1633   -2.7742    0.1537 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.0743   -2.4852   -0.6565 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9629   -1.9830    0.0192 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.7779   -2.8496   -0.1081 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5088   -2.5606    0.0040 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6136   -1.9165   -1.0095 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1663   -2.9963   -1.7695 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3184   -0.9577   -0.3214 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5363   -0.6858   -1.2159 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0410    0.2486   -2.3042 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6743   -0.1250   -0.4574 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.0591   -0.6609   -0.9289 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.0033   -2.1032   -1.2508 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9603   -0.2473    0.1741 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4159   -0.5179    0.0989 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.7781   -1.9190    0.4572 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1110    0.0989   -1.0673 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.8794   -0.6962   -2.2439 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5786    0.2505   -1.0458 C   0  0  2  0  0  0  0  0  0  0  0  0
    9.3118   -1.0777   -1.2756 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1981    1.0352    0.0126 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5921    2.1746   -0.2745 O   0  0  0  0  0  0  0  0  0  0  0  0
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    3.3463    2.9264   -1.8613 O   0  0  0  0  0  0  0  0  0  0  0  0
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    0.7285    5.3693    1.2634 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.4071    5.9052    0.1492 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9749    3.7574    1.6170 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2975    2.7542    0.9687 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4267    3.6539    1.6433 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2007    4.8758    2.0818 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1234    2.5783    1.3337 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8956    1.6821    0.1715 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1726    0.2627    0.6198 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7727   -0.5654   -0.4729 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5829   -4.0441   -0.0393 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7785   -4.2649   -0.6518 C   0  0  2  0  0  0  0  0  0  0  0  0
   -7.8191   -3.9244   -2.1207 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9405   -3.5578    0.0217 C   0  0  1  0  0  0  0  0  0  0  0  0
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    1.8086   -1.6159   -1.7715 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2251    0.8561   -1.8712 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8524    0.8327   -2.7701 H   0  0  0  0  0  0  0  0  0  0  0  0
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    2.6072   -0.5650    0.5908 H   0  0  0  0  0  0  0  0  0  0  0  0
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    3.3580   -2.7089   -0.5881 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6031   -2.2549   -2.2937 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0481   -2.4971   -1.3436 H   0  0  0  0  0  0  0  0  0  0  0  0
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   11.0849    1.9259    1.5755 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6228    3.0964   -1.1754 H   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1652309042215012D          

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  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  6  0  0  0
  5  7  1  0  0  0  0
  7  8  1  1  0  0  0
  7  9  1  0  0  0  0
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 11 12  1  0  0  0  0
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 25 26  1  1  0  0  0
 19 26  1  0  0  0  0
 25 27  1  0  0  0  0
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 37 42  1  0  0  0  0
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 51 52  1  0  0  0  0
 14 52  1  0  0  0  0
 52 53  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0195200

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCC(=O)[C@@H](C)[C@@H](O)[C@H](C)C[C@@H](C)[C@H]1OC(=O)C[C@@]2(O)CC=C(C)[C@H](O2)\C(C)=C\CCC[C@@H](O[C@H]2C[C@@H](OC(O)=N)[C@H](O)[C@@H](C)O2)\C=C\[C@H](C)C[C@H]1C

> <INCHI_IDENTIFIER>
InChI=1S/C41H67NO11/c1-10-32(43)29(8)36(45)26(5)20-28(7)38-27(6)19-23(2)15-16-31(50-35-21-33(51-40(42)47)37(46)30(9)49-35)14-12-11-13-24(3)39-25(4)17-18-41(48,53-39)22-34(44)52-38/h13,15-17,23,26-31,33,35-39,45-46,48H,10-12,14,18-22H2,1-9H3,(H2,42,47)/b16-15+,24-13+/t23-,26+,27+,28+,29+,30+,31+,33+,35-,36-,37+,38-,39+,41+/m0/s1

> <INCHI_KEY>
HHQKNFDAEDTRJK-LIOWZGMGSA-N

> <FORMULA>
C41H67NO11

> <MOLECULAR_WEIGHT>
749.983

> <EXACT_MASS>
749.471411981

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_ATOM_COUNT>
120

> <JCHEM_AVERAGE_POLARIZABILITY>
83.2096781630606

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
{[(2R,3R,4R,6R)-3-hydroxy-6-{[(1R,5S,6R,8R,9E,11R,15E,17R)-1-hydroxy-5-[(2R,4R,5S,6S)-5-hydroxy-4,6-dimethyl-7-oxononan-2-yl]-6,8,16,18-tetramethyl-3-oxo-4,21-dioxabicyclo[15.3.1]henicosa-9,15,18-trien-11-yl]oxy}-2-methyloxan-4-yl]oxy}methanimidic acid

> <JCHEM_LOGP>
4.9731445832170085

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
11.928595299381739

> <JCHEM_PKA_STRONGEST_ACIDIC>
-2.979667540430902

> <JCHEM_PKA_STRONGEST_BASIC>
11.327306901995303

> <JCHEM_POLAR_SURFACE_AREA>
185.05999999999995

> <JCHEM_REFRACTIVITY>
213.33320000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
{[(2R,3R,4R,6R)-3-hydroxy-6-{[(1R,5S,6R,8R,9E,11R,15E,17R)-1-hydroxy-5-[(2R,4R,5S,6S)-5-hydroxy-4,6-dimethyl-7-oxononan-2-yl]-6,8,16,18-tetramethyl-3-oxo-4,21-dioxabicyclo[15.3.1]henicosa-9,15,18-trien-11-yl]oxy}-2-methyloxan-4-yl]oxy}methanimidic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-22         0                                  
HETATM    1  C   UNK     0      -9.336  -2.310   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -8.002  -3.080   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -6.668  -2.310   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      -6.668  -0.770   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      -5.335  -3.080   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -5.335  -4.620   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -4.001  -2.310   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -4.001  -0.770   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      -2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.000  -3.080   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.000  -4.620   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       1.334  -0.770   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      -0.000   0.000   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -1.334  -0.770   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      -0.000   1.540   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      -0.000   3.080   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       5.335   4.620   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       2.667   1.540   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       8.002   0.000   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       9.336  -0.770   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       9.336  -2.310   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      10.669  -3.080   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0      10.669  -4.620   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      12.003  -5.390   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      12.003  -6.930   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0      13.337  -7.700   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0      13.337  -9.240   0.000  0.00  0.00           C+0
HETATM   40  N   UNK     0      14.670 -10.010   0.000  0.00  0.00           N+0
HETATM   41  O   UNK     0      12.003 -10.010   0.000  0.00  0.00           O+0
HETATM   42  C   UNK     0      10.669  -7.700   0.000  0.00  0.00           C+0
HETATM   43  O   UNK     0      10.669  -9.240   0.000  0.00  0.00           O+0
HETATM   44  C   UNK     0       9.336  -6.930   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0       8.002  -7.700   0.000  0.00  0.00           C+0
HETATM   46  O   UNK     0       9.336  -5.390   0.000  0.00  0.00           O+0
HETATM   47  C   UNK     0       8.002  -3.080   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   51  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   52  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   53  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15   52                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19                                                       
CONECT   19   18   20   21   26                                             
CONECT   20   19                                                            
CONECT   21   19   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26   27                                                  
CONECT   26   25   19                                                       
CONECT   27   25   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   34   47                                                  
CONECT   34   33   35                                                       
CONECT   35   34   36   46                                                  
CONECT   36   35   37                                                       
CONECT   37   36   38   42                                                  
CONECT   38   37   39                                                       
CONECT   39   38   40   41                                                  
CONECT   40   39                                                            
CONECT   41   39                                                            
CONECT   42   37   43   44                                                  
CONECT   43   42                                                            
CONECT   44   42   45   46                                                  
CONECT   45   44                                                            
CONECT   46   44   35                                                       
CONECT   47   33   48                                                       
CONECT   48   47   49                                                       
CONECT   49   48   50   51                                                  
CONECT   50   49                                                            
CONECT   51   49   52                                                       
CONECT   52   51   14   53                                                  
CONECT   53   52                                                            
MASTER        0    0    0    0    0    0    0    0   53    0  110    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₄₁H₆₇NO₁₁

Average Mass

749.9830 Da

Monoisotopic Mass

749.47141 Da

IUPAC Name

{[(2R,3R,4R,6R)-3-hydroxy-6-{[(1R,5S,6R,8R,9E,11R,15E,17R)-1-hydroxy-5-[(2R,4R,5S,6S)-5-hydroxy-4,6-dimethyl-7-oxononan-2-yl]-6,8,16,18-tetramethyl-3-oxo-4,21-dioxabicyclo[15.3.1]henicosa-9,15,18-trien-11-yl]oxy}-2-methyloxan-4-yl]oxy}methanimidic acid

Traditional Name

CAS Registry Number

Not Available

SMILES

CCC(=O)[C@@H](C)[C@@H](O)[C@H](C)C[C@@H](C)[C@H]1OC(=O)C[C@@]2(O)CC=C(C)[C@H](O2)\C(C)=C\CCC[C@@H](O[C@H]2C[C@@H](OC(O)=N)[C@H](O)[C@@H](C)O2)\C=C\[C@H](C)C[C@H]1C

InChI Identifier

InChI=1S/C41H67NO11/c1-10-32(43)29(8)36(45)26(5)20-28(7)38-27(6)19-23(2)15-16-31(50-35-21-33(51-40(42)47)37(46)30(9)49-35)14-12-11-13-24(3)39-25(4)17-18-41(48,53-39)22-34(44)52-38/h13,15-17,23,26-31,33,35-39,45-46,48H,10-12,14,18-22H2,1-9H3,(H2,42,47)/b16-15+,24-13+/t23-,26+,27+,28+,29+,30+,31+,33+,35-,36-,37+,38-,39+,41+/m0/s1

InChI Key

HHQKNFDAEDTRJK-LIOWZGMGSA-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 diterpene lactones. These are diterpenoids containing a lactone moiety.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Diterpene lactones

Alternative Parents

Substituents

Diterpene lactone
Diterpenoid
Macrolide
Hexose monosaccharide
Glycosyl compound
O-glycosyl compound
Beta-hydroxy ketone
Monosaccharide
Oxane
Pyran
Carbamic acid ester
Secondary alcohol
Lactone
Ketone
Carboxylic acid ester
Hemiacetal
Carboxylic acid derivative
Acetal
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Oxacycle
Organooxygen compound
Organic oxide
Organopnictogen compound
Organic oxygen compound
Hydrocarbon derivative
Organonitrogen compound
Carbonyl group
Organic nitrogen compound
Aldehyde
Alcohol
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic 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	4.97	ChemAxon
pKa (Strongest Acidic)	-3	ChemAxon
pKa (Strongest Basic)	11.33	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	185.06 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	213.33 m³·mol⁻¹	ChemAxon
Polarizability	83.21 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's 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

8231414

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10055855

PDB ID

Not Available

ChEBI ID

184114

Good Scents ID

Not Available

References

General References

Li H, Zhang M, Li H, Yu H, Chen S, Wu W, Sun P: Discovery of Venturicidin Congeners and Identification of the Biosynthetic Gene Cluster from Streptomyces sp. NRRL S-4. J Nat Prod. 2021 Jan 22;84(1):110-119. doi: 10.1021/acs.jnatprod.0c01177. Epub 2020 Dec 23. [PubMed:33356258 ]
Yarlagadda V, Medina R, Wright GD: Venturicidin A, A Membrane-active Natural Product Inhibitor of ATP synthase Potentiates Aminoglycoside Antibiotics. Sci Rep. 2020 May 18;10(1):8134. doi: 10.1038/s41598-020-64756-0. [PubMed:32424122 ]
Lin J, Weixler D, Daboss S, Seibold GM, Andronescu C, Schuhmann W, Kranz C: Time-resolved ATP measurements during vesicle respiration. Talanta. 2019 Dec 1;205:120083. doi: 10.1016/j.talanta.2019.06.083. Epub 2019 Jun 29. [PubMed:31450430 ]
Otoguro K, Ishiyama A, Namatame M, Nishihara A, Furusawa T, Masuma R, Shiomi K, Takahashi Y, Yamada H, Omura S: Selective and potent in vitro antitrypanosomal activities of ten microbial metabolites. J Antibiot (Tokyo). 2008 Jun;61(6):372-8. doi: 10.1038/ja.2008.52. [PubMed:18667785 ]
Fourati-Ben Fguira L, Smaoui S, Karray-Rebai I, Bejar S, Mellouli L: The antifungal activity of the terrestrial Streptomyces US80 strain is induced by heat-killed fungi. Biotechnol J. 2008 Aug;3(8):1058-66. doi: 10.1002/biot.200700155. [PubMed:18481262 ]
Fourati-Ben Fguira L, Fotso S, Ben Ameur-Mehdi R, Mellouli L, Laatsch H: Purification and structure elucidation of antifungal and antibacterial activities of newly isolated Streptomyces sp. strain US80. Res Microbiol. 2005 Apr;156(3):341-7. doi: 10.1016/j.resmic.2004.10.006. Epub 2004 Dec 15. [PubMed:15808937 ]
LOTUS database [Link]

Showing NP-Card for {[(2r,3r,4r,6r)-3-hydroxy-6-{[(1r,5s,6r,8r,9e,11r,15e,17r)-1-hydroxy-5-[(2r,4r,5s,6s)-5-hydroxy-4,6-dimethyl-7-oxononan-2-yl]-6,8,16,18-tetramethyl-3-oxo-4,21-dioxabicyclo[15.3.1]henicosa-9,15,18-trien-11-yl]oxy}-2-methyloxan-4-yl]oxy}methanimidic acid (NP0195200)

MOL for NP0195200 ({[(2r,3r,4r,6r)-3-hydroxy-6-{[(1r,5s,6r,8r,9e,11r,15e,17r)-1-hydroxy-5-[(2r,4r,5s,6s)-5-hydroxy-4,6-dimethyl-7-oxononan-2-yl]-6,8,16,18-tetramethyl-3-oxo-4,21-dioxabicyclo[15.3.1]henicosa-9,15,18-trien-11-yl]oxy}-2-methyloxan-4-yl]oxy}methanimidic acid)

3D MOL for NP0195200 ({[(2r,3r,4r,6r)-3-hydroxy-6-{[(1r,5s,6r,8r,9e,11r,15e,17r)-1-hydroxy-5-[(2r,4r,5s,6s)-5-hydroxy-4,6-dimethyl-7-oxononan-2-yl]-6,8,16,18-tetramethyl-3-oxo-4,21-dioxabicyclo[15.3.1]henicosa-9,15,18-trien-11-yl]oxy}-2-methyloxan-4-yl]oxy}methanimidic acid)

3D SDF for NP0195200 ({[(2r,3r,4r,6r)-3-hydroxy-6-{[(1r,5s,6r,8r,9e,11r,15e,17r)-1-hydroxy-5-[(2r,4r,5s,6s)-5-hydroxy-4,6-dimethyl-7-oxononan-2-yl]-6,8,16,18-tetramethyl-3-oxo-4,21-dioxabicyclo[15.3.1]henicosa-9,15,18-trien-11-yl]oxy}-2-methyloxan-4-yl]oxy}methanimidic acid)

3D-SDF for NP0195200 ({[(2r,3r,4r,6r)-3-hydroxy-6-{[(1r,5s,6r,8r,9e,11r,15e,17r)-1-hydroxy-5-[(2r,4r,5s,6s)-5-hydroxy-4,6-dimethyl-7-oxononan-2-yl]-6,8,16,18-tetramethyl-3-oxo-4,21-dioxabicyclo[15.3.1]henicosa-9,15,18-trien-11-yl]oxy}-2-methyloxan-4-yl]oxy}methanimidic acid)

PDB for NP0195200 ({[(2r,3r,4r,6r)-3-hydroxy-6-{[(1r,5s,6r,8r,9e,11r,15e,17r)-1-hydroxy-5-[(2r,4r,5s,6s)-5-hydroxy-4,6-dimethyl-7-oxononan-2-yl]-6,8,16,18-tetramethyl-3-oxo-4,21-dioxabicyclo[15.3.1]henicosa-9,15,18-trien-11-yl]oxy}-2-methyloxan-4-yl]oxy}methanimidic acid)

3D PDB for NP0195200 ({[(2r,3r,4r,6r)-3-hydroxy-6-{[(1r,5s,6r,8r,9e,11r,15e,17r)-1-hydroxy-5-[(2r,4r,5s,6s)-5-hydroxy-4,6-dimethyl-7-oxononan-2-yl]-6,8,16,18-tetramethyl-3-oxo-4,21-dioxabicyclo[15.3.1]henicosa-9,15,18-trien-11-yl]oxy}-2-methyloxan-4-yl]oxy}methanimidic acid)

SMILES for NP0195200 ({[(2r,3r,4r,6r)-3-hydroxy-6-{[(1r,5s,6r,8r,9e,11r,15e,17r)-1-hydroxy-5-[(2r,4r,5s,6s)-5-hydroxy-4,6-dimethyl-7-oxononan-2-yl]-6,8,16,18-tetramethyl-3-oxo-4,21-dioxabicyclo[15.3.1]henicosa-9,15,18-trien-11-yl]oxy}-2-methyloxan-4-yl]oxy}methanimidic acid)

INCHI for NP0195200 ({[(2r,3r,4r,6r)-3-hydroxy-6-{[(1r,5s,6r,8r,9e,11r,15e,17r)-1-hydroxy-5-[(2r,4r,5s,6s)-5-hydroxy-4,6-dimethyl-7-oxononan-2-yl]-6,8,16,18-tetramethyl-3-oxo-4,21-dioxabicyclo[15.3.1]henicosa-9,15,18-trien-11-yl]oxy}-2-methyloxan-4-yl]oxy}methanimidic acid)

Structure for NP0195200 ({[(2r,3r,4r,6r)-3-hydroxy-6-{[(1r,5s,6r,8r,9e,11r,15e,17r)-1-hydroxy-5-[(2r,4r,5s,6s)-5-hydroxy-4,6-dimethyl-7-oxononan-2-yl]-6,8,16,18-tetramethyl-3-oxo-4,21-dioxabicyclo[15.3.1]henicosa-9,15,18-trien-11-yl]oxy}-2-methyloxan-4-yl]oxy}methanimidic acid)

3D Structure for NP0195200 ({[(2r,3r,4r,6r)-3-hydroxy-6-{[(1r,5s,6r,8r,9e,11r,15e,17r)-1-hydroxy-5-[(2r,4r,5s,6s)-5-hydroxy-4,6-dimethyl-7-oxononan-2-yl]-6,8,16,18-tetramethyl-3-oxo-4,21-dioxabicyclo[15.3.1]henicosa-9,15,18-trien-11-yl]oxy}-2-methyloxan-4-yl]oxy}methanimidic acid)