NP-MRD: Showing NP-Card for n-[(1r,2r,3r,4s,5r)-2-({7-[(3r,3as,5ar,5br,7as,10r,11as,11br,13ar,13bs)-5a,5b,8,8,10,11a,13b-heptamethyl-hexadecahydrocyclopenta[a]chrysen-3-yl]-2,3,4-tris(acetyloxy)octyl}oxy)-4,5-bis(acetyloxy)-3-[(acetyloxy)methyl]-3-hydroxycyclopentyl]ethanimidic acid (NP0169488)

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Record Information

Version

2.0

Created at

2022-09-03 05:26:59 UTC

Updated at

2022-09-03 05:26:59 UTC

NP-MRD ID

NP0169488

Secondary Accession Numbers

None

Natural Product Identification

Common Name

n-[(1r,2r,3r,4s,5r)-2-({7-[(3r,3as,5ar,5br,7as,10r,11as,11br,13ar,13bs)-5a,5b,8,8,10,11a,13b-heptamethyl-hexadecahydrocyclopenta[a]chrysen-3-yl]-2,3,4-tris(acetyloxy)octyl}oxy)-4,5-bis(acetyloxy)-3-[(acetyloxy)methyl]-3-hydroxycyclopentyl]ethanimidic acid

Description

N-[(1R,2R,3R,4S,5R)-4,5-bis(acetyloxy)-3-[(acetyloxy)methyl]-3-hydroxy-2-{[2,3,4-tris(acetyloxy)-7-[(1R,2R,5S,6R,9S,10R,13R,14S,16R,19S)-1,2,9,14,16,18,18-heptamethylpentacyclo[11.8.0.0²,¹⁰.0⁵,⁹.0¹⁴,¹⁹]Henicosan-6-yl]octyl]oxy}cyclopentyl]ethanimidic acid belongs to the class of organic compounds known as bacteriohopanoids. These are bacterial terpenoids structurally characterized by a C30 skeleton, which is usually conjugated to a C5 (usually hydroxylated) unit linked by a carbon-carbon bond. n-[(1r,2r,3r,4s,5r)-2-({7-[(3r,3as,5ar,5br,7as,10r,11as,11br,13ar,13bs)-5a,5b,8,8,10,11a,13b-heptamethyl-hexadecahydrocyclopenta[a]chrysen-3-yl]-2,3,4-tris(acetyloxy)octyl}oxy)-4,5-bis(acetyloxy)-3-[(acetyloxy)methyl]-3-hydroxycyclopentyl]ethanimidic acid is found in Zymomonas mobilis. Based on a literature review very few articles have been published on N-[(1R,2R,3R,4S,5R)-4,5-bis(acetyloxy)-3-[(acetyloxy)methyl]-3-hydroxy-2-{[2,3,4-tris(acetyloxy)-7-[(1R,2R,5S,6R,9S,10R,13R,14S,16R,19S)-1,2,9,14,16,18,18-heptamethylpentacyclo[11.8.0.0²,¹⁰.0⁵,⁹.0¹⁴,¹⁹]Henicosan-6-yl]octyl]oxy}cyclopentyl]ethanimidic acid.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309032207272D          

 72 77  0  0  1  0            999 V2000
   -0.5816   -9.6221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3945  -10.4256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3949  -10.6654    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9968  -10.9894    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8098  -11.7929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0204  -12.0327    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1356  -11.2225    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3413  -12.7927    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1448  -12.9798    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7086  -12.3774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4688  -11.5880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.2120  -14.1548    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5351  -14.5048    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    4.3122   -9.1407    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1223   -9.2966    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    6.1817   -7.4433    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8054   -7.9834    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.0451   -7.1940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4844   -8.7434    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.9822   -9.4013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    8.1218   -8.5392    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.6195   -9.1972    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    8.7636   -7.0192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   10.4010   -6.8151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2196   -6.7130    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   11.5406   -5.9530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7173   -7.3710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3964   -8.1310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2006   -8.3151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3548   -8.9549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5777   -8.2331    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   10.2568   -8.9931    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4381   -9.0951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9404   -8.4372    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    9.1275   -9.2407    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6919   -8.8289    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2320   -8.2053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0422   -8.3612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9620   -7.4257    0.0000 O   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
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  6  5  1  1  0  0  0
  6  7  1  6  0  0  0
  6  8  1  0  0  0  0
  8  9  1  6  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  2  0  0  0  0
  8 13  1  0  0  0  0
 13 14  1  1  0  0  0
 14 15  1  0  0  0  0
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 13 18  1  0  0  0  0
 18 19  1  6  0  0  0
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 20 21  1  4  0  0  0
 20 22  1  0  0  0  0
 18 23  1  0  0  0  0
  6 23  1  0  0  0  0
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 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
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 28 29  1  0  0  0  0
 28 30  2  0  0  0  0
 26 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 33 35  2  0  0  0  0
 31 36  1  0  0  0  0
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 37 38  1  0  0  0  0
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 41 46  1  0  0  0  0
 46 47  1  1  0  0  0
 47 48  1  0  0  0  0
 48 49  1  0  0  0  0
 49 50  1  1  0  0  0
 49 51  1  0  0  0  0
 44 51  1  0  0  0  0
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 52 53  1  0  0  0  0
 54 53  1  6  0  0  0
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 64 65  1  6  0  0  0
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 66 67  1  0  0  0  0
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 49 67  1  0  0  0  0
 67 68  1  6  0  0  0
 36 69  1  0  0  0  0
 69 70  1  0  0  0  0
 70 71  1  0  0  0  0
 70 72  2  0  0  0  0
M  END

     RDKit          3D

161166  0  0  0  0  0  0  0  0999 V2000
  -10.3501    5.7494   -0.7364 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.3561    4.7864   -0.1123 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1362    4.9260   -0.3779 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.7630    3.7887    0.7188 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9773    2.8440    1.3421 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2931    1.8949    0.4066 C   0  0  2  0  0  0  0  0  0  0  0  0
   -7.4531    2.5285   -0.4634 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2845    0.9782   -0.2921 C   0  0  1  0  0  0  0  0  0  0  0  0
   -9.0689    1.0879   -1.6819 O   0  0  0  0  0  0  0  0  0  0  0  0
  -10.0952    1.5053   -2.5221 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.9250    1.6390   -3.9954 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -9.9206   -2.4577   -0.6522 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.0543   -3.4096   -0.7527 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8460   -2.7267   -1.2628 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4973   -0.1301    1.5978 C   0  0  1  0  0  0  0  0  0  0  0  0
   -8.0086   -1.2782    2.2861 N   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7061   -1.7924    3.2504 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.0127   -1.2327    3.6796 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1778   -2.9132    3.8860 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4838    0.9396    1.3285 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.4504    0.3994    0.5603 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2126    0.7287    1.0500 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0707    0.2144    0.2118 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.1523    0.7057   -1.1133 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2009    1.5079   -1.6729 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3597    1.9780   -3.0658 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.8581   -3.5051    3.1477 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.1831   -0.3907    1.9588 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9293   -0.7303   -0.5412 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.7479   -1.9442   -0.5168 C   0  0  0  0  0  0  0  0  0  0  0  0
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    6.1944   -1.0338    1.2635 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6928    0.6938    0.2616 C   0  0  2  0  0  0  0  0  0  0  0  0
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    9.4815    2.1690    1.2201 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7811    1.5103    1.5844 C   0  0  2  0  0  0  0  0  0  0  0  0
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   11.1113    0.5474   -0.5987 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7321   -0.8287   -0.2970 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6096    0.9456   -1.9423 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6506    0.4019   -0.4551 C   0  0  2  0  0  0  0  0  0  0  0  0
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    6.8366    0.2796   -0.7545 C   0  0  1  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1652309032207272D          

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   11.3548   -8.9549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5777   -8.2331    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   10.2568   -8.9931    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4381   -9.0951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9404   -8.4372    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    9.1275   -9.2407    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6919   -8.8289    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2320   -8.2053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0422   -8.3612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9620   -7.4257    0.0000 O   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
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  6  5  1  1  0  0  0
  6  7  1  6  0  0  0
  6  8  1  0  0  0  0
  8  9  1  6  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  2  0  0  0  0
  8 13  1  0  0  0  0
 13 14  1  1  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  2  0  0  0  0
 13 18  1  0  0  0  0
 18 19  1  6  0  0  0
 19 20  2  0  0  0  0
 20 21  1  4  0  0  0
 20 22  1  0  0  0  0
 18 23  1  0  0  0  0
  6 23  1  0  0  0  0
 23 24  1  6  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 28 30  2  0  0  0  0
 26 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 33 35  2  0  0  0  0
 31 36  1  0  0  0  0
 36 37  1  0  0  0  0
 37 38  1  0  0  0  0
 38 39  1  0  0  0  0
 39 40  1  0  0  0  0
 41 39  1  1  0  0  0
 41 42  1  0  0  0  0
 42 43  1  0  0  0  0
 43 44  1  0  0  0  0
 44 45  1  1  0  0  0
 44 46  1  0  0  0  0
 41 46  1  0  0  0  0
 46 47  1  1  0  0  0
 47 48  1  0  0  0  0
 48 49  1  0  0  0  0
 49 50  1  1  0  0  0
 49 51  1  0  0  0  0
 44 51  1  0  0  0  0
 51 52  1  1  0  0  0
 52 53  1  0  0  0  0
 54 53  1  6  0  0  0
 54 55  1  0  0  0  0
 55 56  1  6  0  0  0
 55 57  1  0  0  0  0
 57 58  1  0  0  0  0
 58 59  1  6  0  0  0
 58 60  1  0  0  0  0
 60 61  1  0  0  0  0
 61 62  1  0  0  0  0
 61 63  1  0  0  0  0
 61 64  1  0  0  0  0
 55 64  1  0  0  0  0
 64 65  1  6  0  0  0
 65 66  1  0  0  0  0
 66 67  1  0  0  0  0
 54 67  1  0  0  0  0
 49 67  1  0  0  0  0
 67 68  1  6  0  0  0
 36 69  1  0  0  0  0
 69 70  1  0  0  0  0
 70 71  1  0  0  0  0
 70 72  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0169488

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(CCC(OC(C)=O)C(OC(C)=O)C(CO[C@@H]1[C@H](N=C(C)O)[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@@]1(O)COC(C)=O)OC(C)=O)[C@H]1CC[C@@]2(C)[C@H]1CC[C@]1(C)[C@@H]2CC[C@@H]2[C@@]3(C)C[C@H](C)CC(C)(C)[C@@H]3CC[C@@]12C

> <INCHI_IDENTIFIER>
InChI=1S/C56H89NO15/c1-30-26-51(10,11)43-22-25-55(15)45(53(43,13)27-30)19-18-44-52(12)23-20-39(40(52)21-24-54(44,55)14)31(2)16-17-41(68-34(5)60)47(70-36(7)62)42(69-35(6)61)28-66-49-46(57-32(3)58)48(71-37(8)63)50(72-38(9)64)56(49,65)29-67-33(4)59/h30-31,39-50,65H,16-29H2,1-15H3,(H,57,58)/t30-,31?,39-,40+,41?,42?,43+,44-,45-,46-,47?,48-,49-,50+,52+,53+,54-,55-,56-/m1/s1

> <INCHI_KEY>
KCYUHKLSVFENND-KPGAEPCTSA-N

> <FORMULA>
C56H89NO15

> <MOLECULAR_WEIGHT>
1016.32

> <EXACT_MASS>
1015.62322117

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
161

> <JCHEM_AVERAGE_POLARIZABILITY>
113.99639325936118

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
N-[(1R,2R,3R,4S,5R)-4,5-bis(acetyloxy)-3-[(acetyloxy)methyl]-3-hydroxy-2-{[2,3,4-tris(acetyloxy)-7-[(1R,2R,5S,6R,9S,10R,13R,14S,16R,19S)-1,2,9,14,16,18,18-heptamethylpentacyclo[11.8.0.0^{2,10}.0^{5,9}.0^{14,19}]henicosan-6-yl]octyl]oxy}cyclopentyl]ethanimidic acid

> <ALOGPS_LOGP>
6.82

> <JCHEM_LOGP>
7.296993302000002

> <ALOGPS_LOGS>
-6.36

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.00261475077074

> <JCHEM_PKA_STRONGEST_ACIDIC>
5.48893111881664

> <JCHEM_PKA_STRONGEST_BASIC>
2.0096181791577163

> <JCHEM_POLAR_SURFACE_AREA>
219.8499999999999

> <JCHEM_REFRACTIVITY>
262.19839999999994

> <JCHEM_ROTATABLE_BOND_COUNT>
23

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.44e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
N-[(1R,2R,3R,4S,5R)-4,5-bis(acetyloxy)-3-[(acetyloxy)methyl]-3-hydroxy-2-{[2,3,4-tris(acetyloxy)-7-[(1R,2R,5S,6R,9S,10R,13R,14S,16R,19S)-1,2,9,14,16,18,18-heptamethylpentacyclo[11.8.0.0^{2,10}.0^{5,9}.0^{14,19}]henicosan-6-yl]octyl]oxy}cyclopentyl]ethanimidic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 03-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-SEP-22         0                                  
HETATM    1  C   UNK     0      -1.086 -17.961   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.736 -19.461   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       0.737 -19.909   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      -1.861 -20.514   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      -1.512 -22.013   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.038 -22.461   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       0.253 -20.949   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -0.637 -23.880   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -2.137 -24.229   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      -3.189 -23.105   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -2.742 -21.631   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -4.689 -23.454   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       0.527 -24.888   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       0.396 -26.422   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      -0.999 -27.076   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -2.262 -26.195   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -1.130 -28.610   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       1.846 -24.092   0.000  0.00  0.00           C+0
HETATM   19  N   UNK     0       3.264 -24.691   0.000  0.00  0.00           N+0
HETATM   20  C   UNK     0       3.455 -26.219   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.874 -26.819   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       2.227 -27.149   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       1.496 -22.592   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       2.505 -21.428   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       2.000 -19.973   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       3.009 -18.809   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       2.505 -17.354   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       0.992 -17.063   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       0.488 -15.608   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      -0.016 -18.227   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       4.521 -19.100   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       5.025 -20.555   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       6.537 -20.846   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       7.545 -19.682   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0       7.041 -22.301   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0       5.529 -17.936   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       7.041 -18.227   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       8.049 -17.063   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       9.562 -17.354   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      10.066 -18.809   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      10.570 -16.190   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0      10.221 -14.690   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0      11.539 -13.894   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0      12.703 -14.902   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0      13.151 -13.429   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0      12.104 -16.321   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0      13.033 -17.549   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0      14.562 -17.359   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0      15.161 -15.940   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0      16.090 -17.168   0.000  0.00  0.00           C+0
HETATM   51  C   UNK     0      14.232 -14.712   0.000  0.00  0.00           C+0
HETATM   52  C   UNK     0      14.831 -13.293   0.000  0.00  0.00           C+0
HETATM   53  C   UNK     0      16.359 -13.103   0.000  0.00  0.00           C+0
HETATM   54  C   UNK     0      17.288 -14.331   0.000  0.00  0.00           C+0
HETATM   55  C   UNK     0      18.816 -14.140   0.000  0.00  0.00           C+0
HETATM   56  C   UNK     0      17.887 -12.912   0.000  0.00  0.00           C+0
HETATM   57  C   UNK     0      19.415 -12.721   0.000  0.00  0.00           C+0
HETATM   58  C   UNK     0      20.943 -12.531   0.000  0.00  0.00           C+0
HETATM   59  C   UNK     0      21.542 -11.112   0.000  0.00  0.00           C+0
HETATM   60  C   UNK     0      21.872 -13.759   0.000  0.00  0.00           C+0
HETATM   61  C   UNK     0      21.273 -15.178   0.000  0.00  0.00           C+0
HETATM   62  C   UNK     0      22.774 -15.521   0.000  0.00  0.00           C+0
HETATM   63  C   UNK     0      21.196 -16.716   0.000  0.00  0.00           C+0
HETATM   64  C   UNK     0      19.745 -15.368   0.000  0.00  0.00           C+0
HETATM   65  C   UNK     0      19.146 -16.787   0.000  0.00  0.00           C+0
HETATM   66  C   UNK     0      17.618 -16.978   0.000  0.00  0.00           C+0
HETATM   67  C   UNK     0      16.689 -15.749   0.000  0.00  0.00           C+0
HETATM   68  C   UNK     0      17.038 -17.249   0.000  0.00  0.00           C+0
HETATM   69  O   UNK     0       5.025 -16.481   0.000  0.00  0.00           O+0
HETATM   70  C   UNK     0       6.033 -15.317   0.000  0.00  0.00           C+0
HETATM   71  C   UNK     0       7.545 -15.608   0.000  0.00  0.00           C+0
HETATM   72  O   UNK     0       5.529 -13.861   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    8   23                                             
CONECT    7    6                                                            
CONECT    8    6    9   13                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10                                                            
CONECT   13    8   14   18                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15                                                            
CONECT   18   13   19   23                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20                                                            
CONECT   23   18    6   24                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27   31                                                  
CONECT   27   26   28                                                       
CONECT   28   27   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28                                                            
CONECT   31   26   32   36                                                  
CONECT   32   31   33                                                       
CONECT   33   32   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33                                                            
CONECT   36   31   37   69                                                  
CONECT   37   36   38                                                       
CONECT   38   37   39                                                       
CONECT   39   38   40   41                                                  
CONECT   40   39                                                            
CONECT   41   39   42   46                                                  
CONECT   42   41   43                                                       
CONECT   43   42   44                                                       
CONECT   44   43   45   46   51                                             
CONECT   45   44                                                            
CONECT   46   44   41   47                                                  
CONECT   47   46   48                                                       
CONECT   48   47   49                                                       
CONECT   49   48   50   51   67                                             
CONECT   50   49                                                            
CONECT   51   49   44   52                                                  
CONECT   52   51   53                                                       
CONECT   53   52   54                                                       
CONECT   54   53   55   67                                                  
CONECT   55   54   56   57   64                                             
CONECT   56   55                                                            
CONECT   57   55   58                                                       
CONECT   58   57   59   60                                                  
CONECT   59   58                                                            
CONECT   60   58   61                                                       
CONECT   61   60   62   63   64                                             
CONECT   62   61                                                            
CONECT   63   61                                                            
CONECT   64   61   55   65                                                  
CONECT   65   64   66                                                       
CONECT   66   65   67                                                       
CONECT   67   66   54   49   68                                             
CONECT   68   67                                                            
CONECT   69   36   70                                                       
CONECT   70   69   71   72                                                  
CONECT   71   70                                                            
CONECT   72   70                                                            
MASTER        0    0    0    0    0    0    0    0   72    0  154    0
END

View in JSmol

Synonyms

Value	Source
N-[(1R,2R,3R,4S,5R)-4,5-Bis(acetyloxy)-3-[(acetyloxy)methyl]-3-hydroxy-2-{[2,3,4-tris(acetyloxy)-7-[(1R,2R,5S,6R,9S,10R,13R,14S,16R,19S)-1,2,9,14,16,18,18-heptamethylpentacyclo[11.8.0.0,.0,.0,]henicosan-6-yl]octyl]oxy}cyclopentyl]ethanimidate	Generator

Chemical Formula

C₅₆H₈₉NO₁₅

Average Mass

1016.3200 Da

Monoisotopic Mass

1015.62322 Da

IUPAC Name

Traditional Name

CAS Registry Number

Not Available

SMILES

CC(CCC(OC(C)=O)C(OC(C)=O)C(CO[C@@H]1[C@H](N=C(C)O)[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@@]1(O)COC(C)=O)OC(C)=O)[C@H]1CC[C@@]2(C)[C@H]1CC[C@]1(C)[C@@H]2CC[C@@H]2[C@@]3(C)C[C@H](C)CC(C)(C)[C@@H]3CC[C@@]12C

InChI Identifier

InChI=1S/C56H89NO15/c1-30-26-51(10,11)43-22-25-55(15)45(53(43,13)27-30)19-18-44-52(12)23-20-39(40(52)21-24-54(44,55)14)31(2)16-17-41(68-34(5)60)47(70-36(7)62)42(69-35(6)61)28-66-49-46(57-32(3)58)48(71-37(8)63)50(72-38(9)64)56(49,65)29-67-33(4)59/h30-31,39-50,65H,16-29H2,1-15H3,(H,57,58)/t30-,31?,39-,40+,41?,42?,43+,44-,45-,46-,47?,48-,49-,50+,52+,53+,54-,55-,56-/m1/s1

InChI Key

KCYUHKLSVFENND-KPGAEPCTSA-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
Zymomonas mobilis	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as bacteriohopanoids. These are bacterial terpenoids structurally characterized by a C30 skeleton, which is usually conjugated to a C5 (usually hydroxylated) unit linked by a carbon-carbon bond.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Hopanoids

Direct Parent

Bacteriohopanoids

Alternative Parents

Substituents

Sesquaterpenoid
Bacteriohopane skeleton
Steroid ester
Hexacarboxylic acid or derivatives
Steroid
Monosaccharide
Cyclopentanol
Cyclitol or derivatives
Tertiary alcohol
Cyclic alcohol
Carboxylic acid ester
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Ether
Dialkyl ether
Carboxylic acid derivative
Carboximidic acid derivative
Carboximidic acid
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Carbonyl group
Alcohol
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic 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	6.82	ALOGPS
logP	7.3	ChemAxon
logS	-6.4	ALOGPS
pKa (Strongest Acidic)	5.49	ChemAxon
pKa (Strongest Basic)	2.01	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	219.85 Å²	ChemAxon
Rotatable Bond Count	23	ChemAxon
Refractivity	262.2 m³·mol⁻¹	ChemAxon
Polarizability	114 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	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

78445166

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

139585740

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for n-[(1r,2r,3r,4s,5r)-2-({7-[(3r,3as,5ar,5br,7as,10r,11as,11br,13ar,13bs)-5a,5b,8,8,10,11a,13b-heptamethyl-hexadecahydrocyclopenta[a]chrysen-3-yl]-2,3,4-tris(acetyloxy)octyl}oxy)-4,5-bis(acetyloxy)-3-[(acetyloxy)methyl]-3-hydroxycyclopentyl]ethanimidic acid (NP0169488)

MOL for NP0169488 (n-[(1r,2r,3r,4s,5r)-2-({7-[(3r,3as,5ar,5br,7as,10r,11as,11br,13ar,13bs)-5a,5b,8,8,10,11a,13b-heptamethyl-hexadecahydrocyclopenta[a]chrysen-3-yl]-2,3,4-tris(acetyloxy)octyl}oxy)-4,5-bis(acetyloxy)-3-[(acetyloxy)methyl]-3-hydroxycyclopentyl]ethanimidic acid)

3D MOL for NP0169488 (n-[(1r,2r,3r,4s,5r)-2-({7-[(3r,3as,5ar,5br,7as,10r,11as,11br,13ar,13bs)-5a,5b,8,8,10,11a,13b-heptamethyl-hexadecahydrocyclopenta[a]chrysen-3-yl]-2,3,4-tris(acetyloxy)octyl}oxy)-4,5-bis(acetyloxy)-3-[(acetyloxy)methyl]-3-hydroxycyclopentyl]ethanimidic acid)

3D SDF for NP0169488 (n-[(1r,2r,3r,4s,5r)-2-({7-[(3r,3as,5ar,5br,7as,10r,11as,11br,13ar,13bs)-5a,5b,8,8,10,11a,13b-heptamethyl-hexadecahydrocyclopenta[a]chrysen-3-yl]-2,3,4-tris(acetyloxy)octyl}oxy)-4,5-bis(acetyloxy)-3-[(acetyloxy)methyl]-3-hydroxycyclopentyl]ethanimidic acid)

3D-SDF for NP0169488 (n-[(1r,2r,3r,4s,5r)-2-({7-[(3r,3as,5ar,5br,7as,10r,11as,11br,13ar,13bs)-5a,5b,8,8,10,11a,13b-heptamethyl-hexadecahydrocyclopenta[a]chrysen-3-yl]-2,3,4-tris(acetyloxy)octyl}oxy)-4,5-bis(acetyloxy)-3-[(acetyloxy)methyl]-3-hydroxycyclopentyl]ethanimidic acid)

PDB for NP0169488 (n-[(1r,2r,3r,4s,5r)-2-({7-[(3r,3as,5ar,5br,7as,10r,11as,11br,13ar,13bs)-5a,5b,8,8,10,11a,13b-heptamethyl-hexadecahydrocyclopenta[a]chrysen-3-yl]-2,3,4-tris(acetyloxy)octyl}oxy)-4,5-bis(acetyloxy)-3-[(acetyloxy)methyl]-3-hydroxycyclopentyl]ethanimidic acid)

3D PDB for NP0169488 (n-[(1r,2r,3r,4s,5r)-2-({7-[(3r,3as,5ar,5br,7as,10r,11as,11br,13ar,13bs)-5a,5b,8,8,10,11a,13b-heptamethyl-hexadecahydrocyclopenta[a]chrysen-3-yl]-2,3,4-tris(acetyloxy)octyl}oxy)-4,5-bis(acetyloxy)-3-[(acetyloxy)methyl]-3-hydroxycyclopentyl]ethanimidic acid)

SMILES for NP0169488 (n-[(1r,2r,3r,4s,5r)-2-({7-[(3r,3as,5ar,5br,7as,10r,11as,11br,13ar,13bs)-5a,5b,8,8,10,11a,13b-heptamethyl-hexadecahydrocyclopenta[a]chrysen-3-yl]-2,3,4-tris(acetyloxy)octyl}oxy)-4,5-bis(acetyloxy)-3-[(acetyloxy)methyl]-3-hydroxycyclopentyl]ethanimidic acid)

INCHI for NP0169488 (n-[(1r,2r,3r,4s,5r)-2-({7-[(3r,3as,5ar,5br,7as,10r,11as,11br,13ar,13bs)-5a,5b,8,8,10,11a,13b-heptamethyl-hexadecahydrocyclopenta[a]chrysen-3-yl]-2,3,4-tris(acetyloxy)octyl}oxy)-4,5-bis(acetyloxy)-3-[(acetyloxy)methyl]-3-hydroxycyclopentyl]ethanimidic acid)

Structure for NP0169488 (n-[(1r,2r,3r,4s,5r)-2-({7-[(3r,3as,5ar,5br,7as,10r,11as,11br,13ar,13bs)-5a,5b,8,8,10,11a,13b-heptamethyl-hexadecahydrocyclopenta[a]chrysen-3-yl]-2,3,4-tris(acetyloxy)octyl}oxy)-4,5-bis(acetyloxy)-3-[(acetyloxy)methyl]-3-hydroxycyclopentyl]ethanimidic acid)

3D Structure for NP0169488 (n-[(1r,2r,3r,4s,5r)-2-({7-[(3r,3as,5ar,5br,7as,10r,11as,11br,13ar,13bs)-5a,5b,8,8,10,11a,13b-heptamethyl-hexadecahydrocyclopenta[a]chrysen-3-yl]-2,3,4-tris(acetyloxy)octyl}oxy)-4,5-bis(acetyloxy)-3-[(acetyloxy)methyl]-3-hydroxycyclopentyl]ethanimidic acid)