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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2021-09-23 17:10:17 UTC

Update Date

2021-09-23 17:10:17 UTC

HMDB ID

HMDB0302357

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Acetyllycopsamine

Description

[1-(acetyloxy)-2,3,5,7a-tetrahydro-1H-pyrrolizin-7-yl]methyl 2,3-dihydroxy-2-(propan-2-yl)butanoate belongs to the class of organic compounds known as alkaloids and derivatives. These are naturally occurring chemical compounds that contain mostly basic nitrogen atoms. This group also includes some related compounds with neutral and even weakly acidic properties. Also some synthetic compounds of similar structure are attributed to alkaloids. In addition to carbon, hydrogen and nitrogen, alkaloids may also contain oxygen, sulfur and more rarely other elements such as chlorine, bromine, and phosphorus. Based on a literature review very few articles have been published on [1-(acetyloxy)-2,3,5,7a-tetrahydro-1H-pyrrolizin-7-yl]methyl 2,3-dihydroxy-2-(propan-2-yl)butanoate.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HMDB0302357
     RDKit          3D
Acetyllycopsamine
 51 52  0  0  0  0  0  0  0  0999 V2000
   -3.4977    0.9837    2.7042 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4697   -0.1623    1.7400 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3675   -1.3373    2.1777 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5515    0.0099    0.3764 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5263   -1.0646   -0.5503 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8073   -1.0084   -1.3967 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4723    0.2098   -2.2671 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0494    0.2393   -2.3986 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4255    1.4131   -1.8522 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1642    0.9239   -1.2368 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1979   -0.3970   -1.1027 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1543   -1.2702   -0.5406 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9893   -0.5342   -0.1157 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0962   -1.1625    0.4467 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9772   -2.4322    0.5371 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2977   -0.4848    0.9048 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1422   -1.5224    1.4467 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1601    0.1140   -0.1700 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6516   -0.9939   -1.1314 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4960    1.1798   -1.0036 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1377    0.4583    2.0513 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3982    1.7215    1.7692 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5636   -0.2187    3.1666 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4951   -0.8413   -1.6287 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0160    1.8724    2.2445 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5169    1.2231    3.1129 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1608    0.6779    3.5497 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4344   -2.0443   -0.0539 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6937   -0.8458   -0.7850 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8267   -1.9202   -2.0122 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8784    1.0829   -1.7238 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0221    0.0724   -3.2117 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0472    1.9985   -1.1794 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1630    2.0718   -2.7206 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3229    1.5365   -0.9323 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5287   -1.9026    0.3016 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2335   -2.0075   -1.2988 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0291   -2.2867    0.8506 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0914    0.5430    0.2511 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8030   -1.5708   -1.5269 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1873   -0.4481   -1.9429 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3237   -1.6898   -0.6109 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0844    1.1925   -1.9700 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4531    0.8755   -1.1994 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6201    2.1563   -0.5176 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1625    0.7276    2.4026 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7618    1.9339    2.6888 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0967    2.5969    1.7417 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7537    1.7304    0.8961 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7223    0.3673    3.9567 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4430   -1.7666   -2.2374 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
 18 20  1  0
 16 21  1  0
 21 22  1  0
 21 23  1  0
 11 24  1  0
 24  5  1  0
 24  8  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  5 28  1  0
  6 29  1  0
  6 30  1  0
  7 31  1  0
  7 32  1  0
  9 33  1  0
  9 34  1  0
 10 35  1  0
 12 36  1  0
 12 37  1  0
 17 38  1  0
 18 39  1  0
 19 40  1  0
 19 41  1  0
 19 42  1  0
 20 43  1  0
 20 44  1  0
 20 45  1  0
 21 46  1  0
 22 47  1  0
 22 48  1  0
 22 49  1  0
 23 50  1  0
 24 51  1  0
M  END


  Mrv0541 02241221462D          

 24 25  0  0  0  0            999 V2000
   -1.5808   -3.6424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3734   -3.4135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9679   -3.9856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5716   -2.6127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3724   -2.8109    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9445   -2.2164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6012   -3.6035    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7707   -2.4145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5419   -1.6219    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1987   -3.0090    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3978   -2.8109    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1742   -3.4053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0295   -4.2175    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7572   -4.6061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3517   -4.0341    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.9914   -3.2920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5858   -2.7199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3136   -3.1085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1689   -3.9208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4725   -1.9028    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7081   -1.5923    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0571   -2.0991    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5947   -0.7752    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7697   -1.8118    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
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  4  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 12 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 15 19  1  0  0  0  0
 17 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
  4 24  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0302357

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(C)C(O)(C(C)O)C(=O)OCC1=CCN2CCC(OC(C)=O)C12

> <INCHI_IDENTIFIER>
InChI=1S/C17H27NO6/c1-10(2)17(22,11(3)19)16(21)23-9-13-5-7-18-8-6-14(15(13)18)24-12(4)20/h5,10-11,14-15,19,22H,6-9H2,1-4H3

> <INCHI_KEY>
RKDOFSJTBIDAHX-UHFFFAOYSA-N

> <FORMULA>
C17H27NO6

> <MOLECULAR_WEIGHT>
341.3994

> <EXACT_MASS>
341.183837601

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
35.4047916313113

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
[1-(acetyloxy)-2,3,5,7a-tetrahydro-1H-pyrrolizin-7-yl]methyl 2,3-dihydroxy-2-(propan-2-yl)butanoate

> <ALOGPS_LOGP>
1.03

> <JCHEM_LOGP>
0.15001041666666667

> <ALOGPS_LOGS>
-1.41

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
14.800899082063157

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.34257485559295

> <JCHEM_PKA_STRONGEST_BASIC>
7.21834769958406

> <JCHEM_POLAR_SURFACE_AREA>
96.3

> <JCHEM_REFRACTIVITY>
87.09400000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.32e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[7-(acetyloxy)-5,6,7,7a-tetrahydro-3H-pyrrolizin-1-yl]methyl 2,3-dihydroxy-2-isopropylbutanoate

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0302357
     RDKit          3D
Acetyllycopsamine
 51 52  0  0  0  0  0  0  0  0999 V2000
   -3.4977    0.9837    2.7042 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4697   -0.1623    1.7400 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3675   -1.3373    2.1777 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5515    0.0099    0.3764 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5263   -1.0646   -0.5503 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8073   -1.0084   -1.3967 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4723    0.2098   -2.2671 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0494    0.2393   -2.3986 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4255    1.4131   -1.8522 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1642    0.9239   -1.2368 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1979   -0.3970   -1.1027 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1543   -1.2702   -0.5406 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9893   -0.5342   -0.1157 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0962   -1.1625    0.4467 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9772   -2.4322    0.5371 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2977   -0.4848    0.9048 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1422   -1.5224    1.4467 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1601    0.1140   -0.1700 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6516   -0.9939   -1.1314 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4960    1.1798   -1.0036 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1377    0.4583    2.0513 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3982    1.7215    1.7692 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5636   -0.2187    3.1666 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4951   -0.8413   -1.6287 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0160    1.8724    2.2445 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5169    1.2231    3.1129 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1608    0.6779    3.5497 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4344   -2.0443   -0.0539 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6937   -0.8458   -0.7850 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8267   -1.9202   -2.0122 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8784    1.0829   -1.7238 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0221    0.0724   -3.2117 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0472    1.9985   -1.1794 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1630    2.0718   -2.7206 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3229    1.5365   -0.9323 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5287   -1.9026    0.3016 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2335   -2.0075   -1.2988 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0291   -2.2867    0.8506 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0914    0.5430    0.2511 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8030   -1.5708   -1.5269 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1873   -0.4481   -1.9429 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3237   -1.6898   -0.6109 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0844    1.1925   -1.9700 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4531    0.8755   -1.1994 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6201    2.1563   -0.5176 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1625    0.7276    2.4026 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7618    1.9339    2.6888 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0967    2.5969    1.7417 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7537    1.7304    0.8961 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7223    0.3673    3.9567 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4430   -1.7666   -2.2374 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
 18 20  1  0
 16 21  1  0
 21 22  1  0
 21 23  1  0
 11 24  1  0
 24  5  1  0
 24  8  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  5 28  1  0
  6 29  1  0
  6 30  1  0
  7 31  1  0
  7 32  1  0
  9 33  1  0
  9 34  1  0
 10 35  1  0
 12 36  1  0
 12 37  1  0
 17 38  1  0
 18 39  1  0
 19 40  1  0
 19 41  1  0
 19 42  1  0
 20 43  1  0
 20 44  1  0
 20 45  1  0
 21 46  1  0
 22 47  1  0
 22 48  1  0
 22 49  1  0
 23 50  1  0
 24 51  1  0
M  END

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      -2.951  -6.799   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -4.430  -6.372   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -5.540  -7.440   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -4.800  -4.877   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -6.295  -5.247   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -7.363  -4.137   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -6.722  -6.727   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -3.305  -4.507   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -2.878  -3.028   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0      -2.238  -5.617   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      -0.743  -5.247   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.325  -6.357   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.055  -7.873   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.413  -8.598   0.000  0.00  0.00           C+0
HETATM   15  N   UNK     0       2.523  -7.530   0.000  0.00  0.00           N+0
HETATM   16  C   UNK     0       1.851  -6.145   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.960  -5.077   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.319  -5.803   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.049  -7.319   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       2.749  -3.552   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       1.322  -2.972   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       0.107  -3.918   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       1.110  -1.447   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      -5.170  -3.382   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5    8   24                                             
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5                                                            
CONECT    8    4    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   16                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   19                                                  
CONECT   16   15   12   17                                                  
CONECT   17   16   18   20                                                  
CONECT   18   17   19                                                       
CONECT   19   18   15                                                       
CONECT   20   17   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21                                                            
CONECT   24    4                                                            
MASTER        0    0    0    0    0    0    0    0   24    0   50    0
END

COMPND    HMDB0302357
HETATM    1  C1  UNL     1      -3.498   0.984   2.704  1.00  0.00           C  
HETATM    2  C2  UNL     1      -3.470  -0.162   1.740  1.00  0.00           C  
HETATM    3  O1  UNL     1      -3.368  -1.337   2.178  1.00  0.00           O  
HETATM    4  O2  UNL     1      -3.551   0.010   0.376  1.00  0.00           O  
HETATM    5  C3  UNL     1      -3.526  -1.065  -0.550  1.00  0.00           C  
HETATM    6  C4  UNL     1      -4.807  -1.008  -1.397  1.00  0.00           C  
HETATM    7  C5  UNL     1      -4.472   0.210  -2.267  1.00  0.00           C  
HETATM    8  N1  UNL     1      -3.049   0.239  -2.399  1.00  0.00           N  
HETATM    9  C6  UNL     1      -2.425   1.413  -1.852  1.00  0.00           C  
HETATM   10  C7  UNL     1      -1.164   0.924  -1.237  1.00  0.00           C  
HETATM   11  C8  UNL     1      -1.198  -0.397  -1.103  1.00  0.00           C  
HETATM   12  C9  UNL     1      -0.154  -1.270  -0.541  1.00  0.00           C  
HETATM   13  O3  UNL     1       0.989  -0.534  -0.116  1.00  0.00           O  
HETATM   14  C10 UNL     1       2.096  -1.163   0.447  1.00  0.00           C  
HETATM   15  O4  UNL     1       1.977  -2.432   0.537  1.00  0.00           O  
HETATM   16  C11 UNL     1       3.298  -0.485   0.905  1.00  0.00           C  
HETATM   17  O5  UNL     1       4.142  -1.522   1.447  1.00  0.00           O  
HETATM   18  C12 UNL     1       4.160   0.114  -0.170  1.00  0.00           C  
HETATM   19  C13 UNL     1       4.652  -0.994  -1.131  1.00  0.00           C  
HETATM   20  C14 UNL     1       3.496   1.180  -1.004  1.00  0.00           C  
HETATM   21  C15 UNL     1       3.138   0.458   2.051  1.00  0.00           C  
HETATM   22  C16 UNL     1       2.398   1.722   1.769  1.00  0.00           C  
HETATM   23  O6  UNL     1       2.564  -0.219   3.167  1.00  0.00           O  
HETATM   24  C17 UNL     1      -2.495  -0.841  -1.629  1.00  0.00           C  
HETATM   25  H1  UNL     1      -4.016   1.872   2.244  1.00  0.00           H  
HETATM   26  H2  UNL     1      -2.517   1.223   3.113  1.00  0.00           H  
HETATM   27  H3  UNL     1      -4.161   0.678   3.550  1.00  0.00           H  
HETATM   28  H4  UNL     1      -3.434  -2.044  -0.054  1.00  0.00           H  
HETATM   29  H5  UNL     1      -5.694  -0.846  -0.785  1.00  0.00           H  
HETATM   30  H6  UNL     1      -4.827  -1.920  -2.012  1.00  0.00           H  
HETATM   31  H7  UNL     1      -4.878   1.083  -1.724  1.00  0.00           H  
HETATM   32  H8  UNL     1      -5.022   0.072  -3.212  1.00  0.00           H  
HETATM   33  H9  UNL     1      -3.047   1.999  -1.179  1.00  0.00           H  
HETATM   34  H10 UNL     1      -2.163   2.072  -2.721  1.00  0.00           H  
HETATM   35  H11 UNL     1      -0.323   1.537  -0.932  1.00  0.00           H  
HETATM   36  H12 UNL     1      -0.529  -1.903   0.302  1.00  0.00           H  
HETATM   37  H13 UNL     1       0.233  -2.008  -1.299  1.00  0.00           H  
HETATM   38  H14 UNL     1       4.029  -2.287   0.851  1.00  0.00           H  
HETATM   39  H15 UNL     1       5.091   0.543   0.251  1.00  0.00           H  
HETATM   40  H16 UNL     1       3.803  -1.571  -1.527  1.00  0.00           H  
HETATM   41  H17 UNL     1       5.187  -0.448  -1.943  1.00  0.00           H  
HETATM   42  H18 UNL     1       5.324  -1.690  -0.611  1.00  0.00           H  
HETATM   43  H19 UNL     1       4.084   1.192  -1.970  1.00  0.00           H  
HETATM   44  H20 UNL     1       2.453   0.875  -1.199  1.00  0.00           H  
HETATM   45  H21 UNL     1       3.620   2.156  -0.518  1.00  0.00           H  
HETATM   46  H22 UNL     1       4.163   0.728   2.403  1.00  0.00           H  
HETATM   47  H23 UNL     1       1.762   1.934   2.689  1.00  0.00           H  
HETATM   48  H24 UNL     1       3.097   2.597   1.742  1.00  0.00           H  
HETATM   49  H25 UNL     1       1.754   1.730   0.896  1.00  0.00           H  
HETATM   50  H26 UNL     1       2.722   0.367   3.957  1.00  0.00           H  
HETATM   51  H27 UNL     1      -2.443  -1.767  -2.237  1.00  0.00           H  
CONECT    1    2   25   26   27
CONECT    2    3    3    4
CONECT    4    5
CONECT    5    6   24   28
CONECT    6    7   29   30
CONECT    7    8   31   32
CONECT    8    9   24
CONECT    9   10   33   34
CONECT   10   11   11   35
CONECT   11   12   24
CONECT   12   13   36   37
CONECT   13   14
CONECT   14   15   15   16
CONECT   16   17   18   21
CONECT   17   38
CONECT   18   19   20   39
CONECT   19   40   41   42
CONECT   20   43   44   45
CONECT   21   22   23   46
CONECT   22   47   48   49
CONECT   23   50
CONECT   24   51
END

HMDB0302357
     RDKit          3D
Acetyllycopsamine
 51 52  0  0  0  0  0  0  0  0999 V2000
   -3.4977    0.9837    2.7042 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4697   -0.1623    1.7400 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3675   -1.3373    2.1777 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5515    0.0099    0.3764 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5263   -1.0646   -0.5503 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8073   -1.0084   -1.3967 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4723    0.2098   -2.2671 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0494    0.2393   -2.3986 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4255    1.4131   -1.8522 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1642    0.9239   -1.2368 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1979   -0.3970   -1.1027 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1543   -1.2702   -0.5406 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9893   -0.5342   -0.1157 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0962   -1.1625    0.4467 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9772   -2.4322    0.5371 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2977   -0.4848    0.9048 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1422   -1.5224    1.4467 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1601    0.1140   -0.1700 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6516   -0.9939   -1.1314 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4960    1.1798   -1.0036 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1377    0.4583    2.0513 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3982    1.7215    1.7692 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5636   -0.2187    3.1666 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4951   -0.8413   -1.6287 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0160    1.8724    2.2445 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5169    1.2231    3.1129 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1608    0.6779    3.5497 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4344   -2.0443   -0.0539 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6937   -0.8458   -0.7850 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8267   -1.9202   -2.0122 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8784    1.0829   -1.7238 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0221    0.0724   -3.2117 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0472    1.9985   -1.1794 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1630    2.0718   -2.7206 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3229    1.5365   -0.9323 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5287   -1.9026    0.3016 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2335   -2.0075   -1.2988 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0291   -2.2867    0.8506 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0914    0.5430    0.2511 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8030   -1.5708   -1.5269 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1873   -0.4481   -1.9429 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3237   -1.6898   -0.6109 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0844    1.1925   -1.9700 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4531    0.8755   -1.1994 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6201    2.1563   -0.5176 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1625    0.7276    2.4026 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7618    1.9339    2.6888 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0967    2.5969    1.7417 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7537    1.7304    0.8961 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7223    0.3673    3.9567 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4430   -1.7666   -2.2374 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
 18 20  1  0
 16 21  1  0
 21 22  1  0
 21 23  1  0
 11 24  1  0
 24  5  1  0
 24  8  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  5 28  1  0
  6 29  1  0
  6 30  1  0
  7 31  1  0
  7 32  1  0
  9 33  1  0
  9 34  1  0
 10 35  1  0
 12 36  1  0
 12 37  1  0
 17 38  1  0
 18 39  1  0
 19 40  1  0
 19 41  1  0
 19 42  1  0
 20 43  1  0
 20 44  1  0
 20 45  1  0
 21 46  1  0
 22 47  1  0
 22 48  1  0
 22 49  1  0
 23 50  1  0
 24 51  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
[1-(Acetyloxy)-2,3,5,7a-tetrahydro-1H-pyrrolizin-7-yl]methyl 2,3-dihydroxy-2-(propan-2-yl)butanoic acid	Generator

Chemical Formula

C₁₇H₂₇NO₆

Average Molecular Weight

341.3994

Monoisotopic Molecular Weight

341.183837601

IUPAC Name

[1-(acetyloxy)-2,3,5,7a-tetrahydro-1H-pyrrolizin-7-yl]methyl 2,3-dihydroxy-2-(propan-2-yl)butanoate

Traditional Name

[7-(acetyloxy)-5,6,7,7a-tetrahydro-3H-pyrrolizin-1-yl]methyl 2,3-dihydroxy-2-isopropylbutanoate

CAS Registry Number

Not Available

SMILES

CC(C)C(O)(C(C)O)C(=O)OCC1=CCN2CCC(OC(C)=O)C12

InChI Identifier

InChI=1S/C17H27NO6/c1-10(2)17(22,11(3)19)16(21)23-9-13-5-7-18-8-6-14(15(13)18)24-12(4)20/h5,10-11,14-15,19,22H,6-9H2,1-4H3

InChI Key

RKDOFSJTBIDAHX-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as alkaloids and derivatives. These are naturally occurring chemical compounds that contain mostly basic nitrogen atoms. This group also includes some related compounds with neutral and even weakly acidic properties. Also some synthetic compounds of similar structure are attributed to alkaloids. In addition to carbon, hydrogen and nitrogen, alkaloids may also contain oxygen, sulfur and more rarely other elements such as chlorine, bromine, and phosphorus.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Not Available

Sub Class

Not Available

Direct Parent

Alkaloids and derivatives

Alternative Parents

Substituents

Alkaloid or derivatives
Pyrrolizine
Beta-hydroxy acid
Fatty acid ester
N-alkylpyrrolidine
Hydroxy acid
Fatty acyl
Dicarboxylic acid or derivatives
Pyrroline
Pyrrolidine
Tertiary alcohol
Tertiary aliphatic amine
Tertiary amine
1,2-diol
Amino acid or derivatives
Carboxylic acid ester
Secondary alcohol
Carboxylic acid derivative
Azacycle
Organoheterocyclic compound
Alcohol
Hydrocarbon derivative
Organic oxide
Organic nitrogen compound
Carbonyl group
Organopnictogen compound
Organic oxygen compound
Amine
Organonitrogen compound
Organooxygen compound
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Exogenous (HMDB: HMDB0302357)

Food

Herb and spice

Oilseed crop

Borage (FooDB: FOOD00026)

Process

Not Available

Role

Biological role

Mutagenic (HMDB: HMDB0302357)

Physical Properties

State

Not Available

Experimental Molecular 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

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	1.03	ALOGPS
logP	0.15	ChemAxon
logS	-1.4	ALOGPS
pKa (Strongest Acidic)	11.34	ChemAxon
pKa (Strongest Basic)	7.22	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	96.3 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	87.09 m³·mol⁻¹	ChemAxon
Polarizability	35.4 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
AllCCS	[M+H]+	180.014	32859911
AllCCS	[M+H-H2O]+	177.313	32859911
AllCCS	[M+Na]+	183.219	32859911
AllCCS	[M+NH4]+	182.506	32859911
AllCCS	[M-H]-	182.831	32859911
AllCCS	[M+Na-2H]-	183.376	32859911
AllCCS	[M+HCOO]-	184.108	32859911
DeepCCS	[M-2H]-	208.565	30932474
DeepCCS	[M+Na]+	183.793	30932474

Predicted Kovats Retention Indices

Not Available

Spectra

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Acetyllycopsamine 10V, Positive-QTOF	splash10-001l-0839000000-a2be6c5d4f2cc1b09606	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Acetyllycopsamine 20V, Positive-QTOF	splash10-001m-6931000000-7192535d5d31f0be896f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Acetyllycopsamine 40V, Positive-QTOF	splash10-000t-3900000000-50099b06ddeda965c4e7	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Acetyllycopsamine 10V, Negative-QTOF	splash10-00kg-3977000000-edfecea9808e48a11e83	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Acetyllycopsamine 20V, Negative-QTOF	splash10-00ke-2941000000-692082994b3cf64c66c4	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Acetyllycopsamine 40V, Negative-QTOF	splash10-01b9-9800000000-2b7fdc36c42ba6795daa	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Acetyllycopsamine 10V, Positive-QTOF	splash10-00di-0029000000-4d1ea9e866ba5dfc5610	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Acetyllycopsamine 20V, Positive-QTOF	splash10-008c-2988000000-2774c64b8a3c9c6c0812	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Acetyllycopsamine 40V, Positive-QTOF	splash10-00e9-1900000000-12a8ff9900fbb723fbba	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Acetyllycopsamine 10V, Negative-QTOF	splash10-014i-3911000000-01d9be965fb43f765e4e	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Acetyllycopsamine 20V, Negative-QTOF	splash10-0aor-9820000000-e82a63b41a5cf391a290	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Acetyllycopsamine 40V, Negative-QTOF	splash10-0a4l-9300000000-108d8f10f5ed97f8c4de	2021-10-21	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB004283

KNApSAcK ID

Not Available

Chemspider ID

509930

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

586647

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Showing metabocard for Acetyllycopsamine (HMDB0302357)

MOL for HMDB0302357 (Acetyllycopsamine)

3D MOL for HMDB0302357 (Acetyllycopsamine)

3D SDF for HMDB0302357 (Acetyllycopsamine)

3D-SDF for HMDB0302357 (Acetyllycopsamine)

PDB for HMDB0302357 (Acetyllycopsamine)

3D PDB for HMDB0302357 (Acetyllycopsamine)

SMILES for HMDB0302357 (Acetyllycopsamine)

INCHI for HMDB0302357 (Acetyllycopsamine)

Structure for HMDB0302357 (Acetyllycopsamine)

3D Structure for HMDB0302357 (Acetyllycopsamine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

MS/MS Spectra