NP-MRD: Showing NP-Card for [(2r,3s,4s,5r,6s)-6-{[(2s,3r,4r,5r,6s)-2-{4-[(2s,11r)-4,11-dihydroxy-9-[(2s)-2-methylbutanoyl]-1,5,9-triazacyclotridec-4-en-2-yl]phenoxy}-4,5-dihydroxy-6-methyloxan-3-yl]oxy}-3,4,5-trihydroxyoxan-2-yl]methyl (2s)-2-methylbutanoate (NP0225853)

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Record Information

Version

2.0

Created at

2022-09-06 04:42:02 UTC

Updated at

2022-09-06 04:42:02 UTC

NP-MRD ID

NP0225853

Secondary Accession Numbers

None

Natural Product Identification

Common Name

[(2r,3s,4s,5r,6s)-6-{[(2s,3r,4r,5r,6s)-2-{4-[(2s,11r)-4,11-dihydroxy-9-[(2s)-2-methylbutanoyl]-1,5,9-triazacyclotridec-4-en-2-yl]phenoxy}-4,5-dihydroxy-6-methyloxan-3-yl]oxy}-3,4,5-trihydroxyoxan-2-yl]methyl (2s)-2-methylbutanoate

Description

[(2R,3S,4S,5R,6S)-6-{[(2S,3R,4R,5R,6S)-2-{4-[(2S,11R)-4,11-dihydroxy-9-[(2S)-2-methylbutanoyl]-1,5,9-triazacyclotridec-4-en-2-yl]phenoxy}-4,5-dihydroxy-6-methyloxan-3-yl]oxy}-3,4,5-trihydroxyoxan-2-yl]methyl (2S)-2-methylbutanoate belongs to the class of organic compounds known as saccharolipids. Saccharolipids are compounds in which fatty acids are linked directly to a sugar backbone, forming structures that are compatible with membrane bilayers. In the saccharolipids, a sugar substitutes for the glycerol backbone that is present in glycerolipids and glycerophospholipids. The most familiar saccharolipids contain an acylated glucosamine. In contrast to others glycolipids, the fatty acid is not glycosidically linked to the sugar moiety. [(2r,3s,4s,5r,6s)-6-{[(2s,3r,4r,5r,6s)-2-{4-[(2s,11r)-4,11-dihydroxy-9-[(2s)-2-methylbutanoyl]-1,5,9-triazacyclotridec-4-en-2-yl]phenoxy}-4,5-dihydroxy-6-methyloxan-3-yl]oxy}-3,4,5-trihydroxyoxan-2-yl]methyl (2s)-2-methylbutanoate is found in Meehania urticifolia. Based on a literature review very few articles have been published on [(2R,3S,4S,5R,6S)-6-{[(2S,3R,4R,5R,6S)-2-{4-[(2S,11R)-4,11-dihydroxy-9-[(2S)-2-methylbutanoyl]-1,5,9-triazacyclotridec-4-en-2-yl]phenoxy}-4,5-dihydroxy-6-methyloxan-3-yl]oxy}-3,4,5-trihydroxyoxan-2-yl]methyl (2S)-2-methylbutanoate.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309062206422D          

 55 58  0  0  1  0            999 V2000
   -8.1205   -6.3160    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4060   -6.7285    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6916   -6.3160    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.6916   -5.4910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9771   -6.7285    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9771   -7.5535    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2626   -6.3160    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5482   -6.7285    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8337   -6.3160    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.1192   -6.7285    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4047   -6.3160    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6903   -6.7285    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6903   -7.5535    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9758   -7.9660    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2613   -7.5535    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4531   -7.9660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1676   -7.5535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8821   -7.9660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8821   -8.7910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5965   -9.2035    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7433   -8.3916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5607   -8.2803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9511   -7.5535    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9192   -9.0234    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.7392   -9.4011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8505  -10.2185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1982  -10.7237    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3096  -11.5411    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.0732  -11.8534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1845  -12.6709    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7254  -11.3483    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.6141  -10.5308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4890  -11.6606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6004  -12.4781    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6573  -12.0463    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8937  -11.7340    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2414  -12.2391    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7824  -10.9165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0188  -10.6042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9074   -9.7867    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1676   -9.2035    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4531   -8.7910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9758   -8.7910    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6903   -9.2035    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6903  -10.0285    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4047   -8.7910    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.1192   -9.2035    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4047   -7.9660    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.1192   -7.5535    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4047   -5.4910    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6903   -5.0785    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1192   -5.0785    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.1192   -4.2535    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8337   -5.4910    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.5482   -5.0785    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  6  0  0  0
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  9  8  1  6  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  6  0  0  0
 13 12  1  1  0  0  0
 13 14  1  0  0  0  0
 14 15  1  6  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 20 19  1  1  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  2  0  0  0  0
 24 25  1  4  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 29 31  1  0  0  0  0
 31 32  1  1  0  0  0
 31 33  1  0  0  0  0
 33 34  1  0  0  0  0
 28 35  1  0  0  0  0
 35 36  1  0  0  0  0
 36 37  1  6  0  0  0
 36 38  1  0  0  0  0
 38 39  1  0  0  0  0
 39 40  1  0  0  0  0
 20 40  1  0  0  0  0
 19 41  1  0  0  0  0
 41 42  2  0  0  0  0
 16 42  1  0  0  0  0
 14 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
 46 47  1  6  0  0  0
 46 48  1  0  0  0  0
 13 48  1  0  0  0  0
 48 49  1  1  0  0  0
 11 50  1  0  0  0  0
 50 51  1  1  0  0  0
 50 52  1  0  0  0  0
 52 53  1  6  0  0  0
 52 54  1  0  0  0  0
  9 54  1  0  0  0  0
 54 55  1  1  0  0  0
M  END


  Mrv1652309062206422D          

 55 58  0  0  1  0            999 V2000
   -8.1205   -6.3160    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4060   -6.7285    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6916   -6.3160    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.6916   -5.4910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9771   -6.7285    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9771   -7.5535    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2626   -6.3160    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5482   -6.7285    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8337   -6.3160    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.1192   -6.7285    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4047   -6.3160    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6903   -6.7285    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6903   -7.5535    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9758   -7.9660    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2613   -7.5535    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4531   -7.9660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1676   -7.5535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8821   -7.9660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8821   -8.7910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5965   -9.2035    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7433   -8.3916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5607   -8.2803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9511   -7.5535    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9192   -9.0234    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.7392   -9.4011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8505  -10.2185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1982  -10.7237    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3096  -11.5411    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.0732  -11.8534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1845  -12.6709    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7254  -11.3483    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.6141  -10.5308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4890  -11.6606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6004  -12.4781    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6573  -12.0463    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8937  -11.7340    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2414  -12.2391    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7824  -10.9165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0188  -10.6042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9074   -9.7867    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1676   -9.2035    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4531   -8.7910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9758   -8.7910    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6903   -9.2035    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6903  -10.0285    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4047   -8.7910    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.1192   -9.2035    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4047   -7.9660    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.1192   -7.5535    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4047   -5.4910    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6903   -5.0785    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1192   -5.0785    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.1192   -4.2535    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8337   -5.4910    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.5482   -5.0785    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  6  0  0  0
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  9  8  1  6  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  6  0  0  0
 13 12  1  1  0  0  0
 13 14  1  0  0  0  0
 14 15  1  6  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 20 19  1  1  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  2  0  0  0  0
 24 25  1  4  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 29 31  1  0  0  0  0
 31 32  1  1  0  0  0
 31 33  1  0  0  0  0
 33 34  1  0  0  0  0
 28 35  1  0  0  0  0
 35 36  1  0  0  0  0
 36 37  1  6  0  0  0
 36 38  1  0  0  0  0
 38 39  1  0  0  0  0
 39 40  1  0  0  0  0
 20 40  1  0  0  0  0
 19 41  1  0  0  0  0
 41 42  2  0  0  0  0
 16 42  1  0  0  0  0
 14 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
 46 47  1  6  0  0  0
 46 48  1  0  0  0  0
 13 48  1  0  0  0  0
 48 49  1  1  0  0  0
 11 50  1  0  0  0  0
 50 51  1  1  0  0  0
 50 52  1  0  0  0  0
 52 53  1  6  0  0  0
 52 54  1  0  0  0  0
  9 54  1  0  0  0  0
 54 55  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0225853

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC[C@H](C)C(=O)OC[C@H]1O[C@@H](O[C@@H]2[C@H](O)[C@@H](O)[C@H](C)O[C@H]2OC2=CC=C(C=C2)[C@@H]2CC(O)=NCCCN(C[C@H](O)CCN2)C(=O)[C@@H](C)CC)[C@H](O)[C@@H](O)[C@@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C38H61N3O14/c1-6-20(3)35(49)41-16-8-14-40-28(43)17-26(39-15-13-24(42)18-41)23-9-11-25(12-10-23)53-38-34(32(47)29(44)22(5)52-38)55-37-33(48)31(46)30(45)27(54-37)19-51-36(50)21(4)7-2/h9-12,20-22,24,26-27,29-34,37-39,42,44-48H,6-8,13-19H2,1-5H3,(H,40,43)/t20-,21-,22-,24+,26-,27+,29-,30+,31-,32+,33+,34+,37-,38-/m0/s1

> <INCHI_KEY>
LAKJMQZPQITUGL-CDIKTVDDSA-N

> <FORMULA>
C38H61N3O14

> <MOLECULAR_WEIGHT>
783.913

> <EXACT_MASS>
783.415353656

> <JCHEM_ACCEPTOR_COUNT>
15

> <JCHEM_ATOM_COUNT>
116

> <JCHEM_AVERAGE_POLARIZABILITY>
83.60195839388572

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
8

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
[(2R,3S,4S,5R,6S)-6-{[(2S,3R,4R,5R,6S)-2-{4-[(2S,11R)-4,11-dihydroxy-9-[(2S)-2-methylbutanoyl]-1,5,9-triazacyclotridec-4-en-2-yl]phenoxy}-4,5-dihydroxy-6-methyloxan-3-yl]oxy}-3,4,5-trihydroxyoxan-2-yl]methyl (2S)-2-methylbutanoate

> <JCHEM_LOGP>
-1.6592135657435105

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
12.1012853956396

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.4285996482003145

> <JCHEM_PKA_STRONGEST_BASIC>
7.914974712705013

> <JCHEM_POLAR_SURFACE_AREA>
249.52999999999994

> <JCHEM_REFRACTIVITY>
194.7666

> <JCHEM_ROTATABLE_BOND_COUNT>
12

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
[(2R,3S,4S,5R,6S)-6-{[(2S,3R,4R,5R,6S)-2-{4-[(2S,11R)-4,11-dihydroxy-9-[(2S)-2-methylbutanoyl]-1,5,9-triazacyclotridec-4-en-2-yl]phenoxy}-4,5-dihydroxy-6-methyloxan-3-yl]oxy}-3,4,5-trihydroxyoxan-2-yl]methyl (2S)-2-methylbutanoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-SEP-22         0                                  
HETATM    1  C   UNK     0     -15.158 -11.790   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0     -13.825 -12.560   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0     -12.491 -11.790   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0     -12.491 -10.250   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0     -11.157 -12.560   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0     -11.157 -14.100   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0      -9.824 -11.790   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -8.490 -12.560   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -7.156 -11.790   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      -5.823 -12.560   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      -4.489 -11.790   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -3.155 -12.560   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      -3.155 -14.100   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.822 -14.870   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -0.488 -14.100   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       0.846 -14.870   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.180 -14.100   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.513 -14.870   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.513 -16.410   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.847 -17.180   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       5.121 -15.664   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       6.647 -15.457   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       7.375 -14.100   0.000  0.00  0.00           O+0
HETATM   24  N   UNK     0       7.316 -16.844   0.000  0.00  0.00           N+0
HETATM   25  C   UNK     0       8.846 -17.549   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       9.054 -19.075   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       7.837 -20.018   0.000  0.00  0.00           C+0
HETATM   28  N   UNK     0       8.045 -21.543   0.000  0.00  0.00           N+0
HETATM   29  C   UNK     0       9.470 -22.126   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       9.678 -23.652   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      10.687 -21.183   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      10.480 -19.658   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      12.113 -21.766   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      12.321 -23.292   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       6.827 -22.486   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       5.402 -21.903   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0       4.184 -22.846   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0       5.194 -20.377   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       3.768 -19.794   0.000  0.00  0.00           C+0
HETATM   40  N   UNK     0       3.561 -18.269   0.000  0.00  0.00           N+0
HETATM   41  C   UNK     0       2.180 -17.180   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0       0.846 -16.410   0.000  0.00  0.00           C+0
HETATM   43  O   UNK     0      -1.822 -16.410   0.000  0.00  0.00           O+0
HETATM   44  C   UNK     0      -3.155 -17.180   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0      -3.155 -18.720   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0      -4.489 -16.410   0.000  0.00  0.00           C+0
HETATM   47  O   UNK     0      -5.823 -17.180   0.000  0.00  0.00           O+0
HETATM   48  C   UNK     0      -4.489 -14.870   0.000  0.00  0.00           C+0
HETATM   49  O   UNK     0      -5.823 -14.100   0.000  0.00  0.00           O+0
HETATM   50  C   UNK     0      -4.489 -10.250   0.000  0.00  0.00           C+0
HETATM   51  O   UNK     0      -3.155  -9.480   0.000  0.00  0.00           O+0
HETATM   52  C   UNK     0      -5.823  -9.480   0.000  0.00  0.00           C+0
HETATM   53  O   UNK     0      -5.823  -7.940   0.000  0.00  0.00           O+0
HETATM   54  C   UNK     0      -7.156 -10.250   0.000  0.00  0.00           C+0
HETATM   55  O   UNK     0      -8.490  -9.480   0.000  0.00  0.00           O+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                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   54                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   50                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   48                                                  
CONECT   14   13   15   43                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   42                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   41                                                  
CONECT   20   19   21   40                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29   35                                                  
CONECT   29   28   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31   34                                                       
CONECT   34   33                                                            
CONECT   35   28   36                                                       
CONECT   36   35   37   38                                                  
CONECT   37   36                                                            
CONECT   38   36   39                                                       
CONECT   39   38   40                                                       
CONECT   40   39   20                                                       
CONECT   41   19   42                                                       
CONECT   42   41   16                                                       
CONECT   43   14   44                                                       
CONECT   44   43   45   46                                                  
CONECT   45   44                                                            
CONECT   46   44   47   48                                                  
CONECT   47   46                                                            
CONECT   48   46   13   49                                                  
CONECT   49   48                                                            
CONECT   50   11   51   52                                                  
CONECT   51   50                                                            
CONECT   52   50   53   54                                                  
CONECT   53   52                                                            
CONECT   54   52    9   55                                                  
CONECT   55   54                                                            
MASTER        0    0    0    0    0    0    0    0   55    0  116    0
END

View in JSmol

Synonyms

Value	Source
[(2R,3S,4S,5R,6S)-6-{[(2S,3R,4R,5R,6S)-2-{4-[(2S,11R)-4,11-dihydroxy-9-[(2S)-2-methylbutanoyl]-1,5,9-triazacyclotridec-4-en-2-yl]phenoxy}-4,5-dihydroxy-6-methyloxan-3-yl]oxy}-3,4,5-trihydroxyoxan-2-yl]methyl (2S)-2-methylbutanoic acid	Generator

Chemical Formula

C₃₈H₆₁N₃O₁₄

Average Mass

783.9130 Da

Monoisotopic Mass

783.41535 Da

IUPAC Name

Traditional Name

CAS Registry Number

Not Available

SMILES

CC[C@H](C)C(=O)OC[C@H]1O[C@@H](O[C@@H]2[C@H](O)[C@@H](O)[C@H](C)O[C@H]2OC2=CC=C(C=C2)[C@@H]2CC(O)=NCCCN(C[C@H](O)CCN2)C(=O)[C@@H](C)CC)[C@H](O)[C@@H](O)[C@@H]1O

InChI Identifier

InChI=1S/C38H61N3O14/c1-6-20(3)35(49)41-16-8-14-40-28(43)17-26(39-15-13-24(42)18-41)23-9-11-25(12-10-23)53-38-34(32(47)29(44)22(5)52-38)55-37-33(48)31(46)30(45)27(54-37)19-51-36(50)21(4)7-2/h9-12,20-22,24,26-27,29-34,37-39,42,44-48H,6-8,13-19H2,1-5H3,(H,40,43)/t20-,21-,22-,24+,26-,27+,29-,30+,31-,32+,33+,34+,37-,38-/m0/s1

InChI Key

LAKJMQZPQITUGL-CDIKTVDDSA-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
Meehania urticifolia	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as saccharolipids. Saccharolipids are compounds in which fatty acids are linked directly to a sugar backbone, forming structures that are compatible with membrane bilayers. In the saccharolipids, a sugar substitutes for the glycerol backbone that is present in glycerolipids and glycerophospholipids. The most familiar saccharolipids contain an acylated glucosamine. In contrast to others glycolipids, the fatty acid is not glycosidically linked to the sugar moiety.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Saccharolipids

Sub Class

Not Available

Direct Parent

Saccharolipids

Alternative Parents

Substituents

Saccharolipid
Phenolic glycoside
Macrolactam
Beta amino acid or derivatives
Disaccharide
Glycosyl compound
O-glycosyl compound
Phenoxy compound
Phenol ether
Fatty acid ester
Aralkylamine
Monocyclic benzene moiety
Oxane
Benzenoid
Fatty acyl
Tertiary carboxylic acid amide
Secondary carboxylic acid amide
Secondary alcohol
Amino acid or derivatives
Lactam
Carboxamide group
Carboxylic acid ester
Secondary amine
Polyol
Azacycle
Organoheterocyclic compound
Oxacycle
Monocarboxylic acid or derivatives
Acetal
Carboxylic acid derivative
Secondary aliphatic amine
Alcohol
Organic oxygen compound
Organopnictogen compound
Organic oxide
Carbonyl group
Organic nitrogen compound
Hydrocarbon derivative
Organonitrogen compound
Amine
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	ChemAxon
pKa (Strongest Acidic)	3.43	ChemAxon
pKa (Strongest Basic)	7.91	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	15	ChemAxon
Hydrogen Donor Count	8	ChemAxon
Polar Surface Area	249.53 Å²	ChemAxon
Rotatable Bond Count	12	ChemAxon
Refractivity	194.77 m³·mol⁻¹	ChemAxon
Polarizability	83.6 Å³	ChemAxon
Number of Rings	4	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

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

44179262

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for [(2r,3s,4s,5r,6s)-6-{[(2s,3r,4r,5r,6s)-2-{4-[(2s,11r)-4,11-dihydroxy-9-[(2s)-2-methylbutanoyl]-1,5,9-triazacyclotridec-4-en-2-yl]phenoxy}-4,5-dihydroxy-6-methyloxan-3-yl]oxy}-3,4,5-trihydroxyoxan-2-yl]methyl (2s)-2-methylbutanoate (NP0225853)

MOL for NP0225853 ([(2r,3s,4s,5r,6s)-6-{[(2s,3r,4r,5r,6s)-2-{4-[(2s,11r)-4,11-dihydroxy-9-[(2s)-2-methylbutanoyl]-1,5,9-triazacyclotridec-4-en-2-yl]phenoxy}-4,5-dihydroxy-6-methyloxan-3-yl]oxy}-3,4,5-trihydroxyoxan-2-yl]methyl (2s)-2-methylbutanoate)

3D MOL for NP0225853 ([(2r,3s,4s,5r,6s)-6-{[(2s,3r,4r,5r,6s)-2-{4-[(2s,11r)-4,11-dihydroxy-9-[(2s)-2-methylbutanoyl]-1,5,9-triazacyclotridec-4-en-2-yl]phenoxy}-4,5-dihydroxy-6-methyloxan-3-yl]oxy}-3,4,5-trihydroxyoxan-2-yl]methyl (2s)-2-methylbutanoate)

3D SDF for NP0225853 ([(2r,3s,4s,5r,6s)-6-{[(2s,3r,4r,5r,6s)-2-{4-[(2s,11r)-4,11-dihydroxy-9-[(2s)-2-methylbutanoyl]-1,5,9-triazacyclotridec-4-en-2-yl]phenoxy}-4,5-dihydroxy-6-methyloxan-3-yl]oxy}-3,4,5-trihydroxyoxan-2-yl]methyl (2s)-2-methylbutanoate)

3D-SDF for NP0225853 ([(2r,3s,4s,5r,6s)-6-{[(2s,3r,4r,5r,6s)-2-{4-[(2s,11r)-4,11-dihydroxy-9-[(2s)-2-methylbutanoyl]-1,5,9-triazacyclotridec-4-en-2-yl]phenoxy}-4,5-dihydroxy-6-methyloxan-3-yl]oxy}-3,4,5-trihydroxyoxan-2-yl]methyl (2s)-2-methylbutanoate)

PDB for NP0225853 ([(2r,3s,4s,5r,6s)-6-{[(2s,3r,4r,5r,6s)-2-{4-[(2s,11r)-4,11-dihydroxy-9-[(2s)-2-methylbutanoyl]-1,5,9-triazacyclotridec-4-en-2-yl]phenoxy}-4,5-dihydroxy-6-methyloxan-3-yl]oxy}-3,4,5-trihydroxyoxan-2-yl]methyl (2s)-2-methylbutanoate)

3D PDB for NP0225853 ([(2r,3s,4s,5r,6s)-6-{[(2s,3r,4r,5r,6s)-2-{4-[(2s,11r)-4,11-dihydroxy-9-[(2s)-2-methylbutanoyl]-1,5,9-triazacyclotridec-4-en-2-yl]phenoxy}-4,5-dihydroxy-6-methyloxan-3-yl]oxy}-3,4,5-trihydroxyoxan-2-yl]methyl (2s)-2-methylbutanoate)

SMILES for NP0225853 ([(2r,3s,4s,5r,6s)-6-{[(2s,3r,4r,5r,6s)-2-{4-[(2s,11r)-4,11-dihydroxy-9-[(2s)-2-methylbutanoyl]-1,5,9-triazacyclotridec-4-en-2-yl]phenoxy}-4,5-dihydroxy-6-methyloxan-3-yl]oxy}-3,4,5-trihydroxyoxan-2-yl]methyl (2s)-2-methylbutanoate)

INCHI for NP0225853 ([(2r,3s,4s,5r,6s)-6-{[(2s,3r,4r,5r,6s)-2-{4-[(2s,11r)-4,11-dihydroxy-9-[(2s)-2-methylbutanoyl]-1,5,9-triazacyclotridec-4-en-2-yl]phenoxy}-4,5-dihydroxy-6-methyloxan-3-yl]oxy}-3,4,5-trihydroxyoxan-2-yl]methyl (2s)-2-methylbutanoate)

Structure for NP0225853 ([(2r,3s,4s,5r,6s)-6-{[(2s,3r,4r,5r,6s)-2-{4-[(2s,11r)-4,11-dihydroxy-9-[(2s)-2-methylbutanoyl]-1,5,9-triazacyclotridec-4-en-2-yl]phenoxy}-4,5-dihydroxy-6-methyloxan-3-yl]oxy}-3,4,5-trihydroxyoxan-2-yl]methyl (2s)-2-methylbutanoate)

3D Structure for NP0225853 ([(2r,3s,4s,5r,6s)-6-{[(2s,3r,4r,5r,6s)-2-{4-[(2s,11r)-4,11-dihydroxy-9-[(2s)-2-methylbutanoyl]-1,5,9-triazacyclotridec-4-en-2-yl]phenoxy}-4,5-dihydroxy-6-methyloxan-3-yl]oxy}-3,4,5-trihydroxyoxan-2-yl]methyl (2s)-2-methylbutanoate)