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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-08-29 23:33:46 UTC

Update Date

2021-09-26 22:48:56 UTC

HMDB ID

HMDB0242334

Secondary Accession Numbers

None

Metabolite Identification

Common Name

(1R,4E,6S,7S,17R)-4-Ethylidene-7-hydroxy-7-(hydroxymethyl)-6-methyl-2,9-dioxa-14-azatricyclo[9.5.1.014,17]heptadec-11-ene-3,8-dione

Description

Usaramine, also known as retrorsine, belongs to the class of organic compounds known as macrolides and analogues. These are organic compounds containing a lactone ring of at least twelve members. Usaramine is a very strong basic compound (based on its pKa). This compound has been identified in human blood as reported by (PMID: 31557052 ). (1r,4e,6s,7s,17r)-4-ethylidene-7-hydroxy-7-(hydroxymethyl)-6-methyl-2,9-dioxa-14-azatricyclo[9.5.1.014,17]heptadec-11-ene-3,8-dione is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically (1R,4E,6S,7S,17R)-4-Ethylidene-7-hydroxy-7-(hydroxymethyl)-6-methyl-2,9-dioxa-14-azatricyclo[9.5.1.014,17]heptadec-11-ene-3,8-dione is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.

Structure

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


  Mrv1533004171501402D          

 25 27  0  0  0  0            999 V2000
    6.7709    3.1074    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9824    2.8648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7982    2.0606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4026    1.4990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2184    0.6948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4299    0.4522    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8228    0.1333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2709    0.8260    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5828   -0.1877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2408    0.3100    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6386   -0.6709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2430   -1.2325    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8501   -0.9135    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2458   -0.3520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4572   -0.5946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9619   -1.2543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1814   -0.9871    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1943   -0.1622    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7199    0.5127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2152    1.1725    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0370    0.7712    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8255    1.0138    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0097    1.8180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4053    2.3796    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8529   -0.0330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  4  0  0  0
  2  3  2  0  0  0  0
  3  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
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
  7 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  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
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
  3 23  1  0  0  0  0
 23 24  2  0  0  0  0
 21 25  1  0  0  0  0
 15 25  1  0  0  0  0
 18 25  1  0  0  0  0
M  END

HMDB0242585
     RDKit          3D
Usaramine
 50 52  0  0  0  0  0  0  0  0999 V2000
   -1.0393    4.3682    0.2549 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7115    3.1312   -0.1615 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1000    2.0572   -0.6679 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8978    0.8839   -1.0436 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9802   -0.1869    0.0319 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9133    0.2296    1.1198 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4652   -1.4306   -0.6693 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5718   -1.0147   -1.4561 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9728   -2.5130    0.2043 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0144   -2.0207    0.9871 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3662   -1.8612   -1.5756 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7146   -2.2000   -2.7614 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0435   -1.9282   -1.2696 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5964   -2.4874   -0.1757 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9941   -1.9540   -0.0507 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1697   -2.3581   -0.5126 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2462   -1.4344   -0.0713 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6218   -0.8508    1.1015 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1245    0.4699    1.3111 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9714    1.4068    1.0219 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2154    0.5599   -0.0200 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1106    1.0685   -0.5566 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3738    2.1318   -0.8326 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7260    3.3043   -1.2498 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2059   -0.7331    0.7160 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0600    4.1585    0.7726 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8850    5.0960   -0.5705 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6750    4.8836    1.0024 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8004    3.0853   -0.0510 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5484    0.3878   -1.9754 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9415    1.2042   -1.2462 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9559   -0.2682    0.4397 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7210   -0.4155    2.0263 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9636    0.2859    0.8321 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6305    1.2511    1.4753 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2889   -0.9320   -2.4188 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2235   -3.0393    0.8227 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4410   -3.2822   -0.4689 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8871   -2.0226    0.5128 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6176   -3.6066   -0.3465 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0564   -2.3945    0.7972 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3093   -3.2346   -1.1208 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1398   -2.0129    0.3064 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6159   -0.7427   -0.8098 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9642    0.7210    0.6297 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5205    0.6281    2.3497 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2750    2.3687    0.6108 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3427    1.4776    1.9387 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9891    0.4462   -0.8434 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6262   -0.6812    1.6602 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  3
  3  4  1  0
  4  5  1  0
  5  6  1  0
  5  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
  7 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  2  0
 21 25  1  0
 23  3  1  0
 25 15  1  0
 25 18  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  2 29  1  0
  4 30  1  0
  4 31  1  0
  5 32  1  0
  6 33  1  0
  6 34  1  0
  6 35  1  0
  8 36  1  0
  9 37  1  0
  9 38  1  0
 10 39  1  0
 14 40  1  0
 14 41  1  0
 16 42  1  0
 17 43  1  0
 17 44  1  0
 19 45  1  0
 19 46  1  0
 20 47  1  0
 20 48  1  0
 21 49  1  0
 25 50  1  0
M  END


  Mrv1533004171501402D          

 25 27  0  0  0  0            999 V2000
    6.7709    3.1074    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9824    2.8648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7982    2.0606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4026    1.4990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2184    0.6948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4299    0.4522    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8228    0.1333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2709    0.8260    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5828   -0.1877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2408    0.3100    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6386   -0.6709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2430   -1.2325    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8501   -0.9135    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2458   -0.3520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4572   -0.5946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9619   -1.2543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1814   -0.9871    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1943   -0.1622    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7199    0.5127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2152    1.1725    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0370    0.7712    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8255    1.0138    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0097    1.8180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4053    2.3796    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8529   -0.0330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  4  0  0  0
  2  3  2  0  0  0  0
  3  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
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
  7 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  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
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
  3 23  1  0  0  0  0
 23 24  2  0  0  0  0
 21 25  1  0  0  0  0
 15 25  1  0  0  0  0
 18 25  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0242334

> <DATABASE_NAME>
hmdb

> <SMILES>
CC=C1CC(C)C(O)(CO)C(=O)OCC2=CCN3CCC(OC1=O)C23

> <INCHI_IDENTIFIER>
InChI=1S/C18H25NO6/c1-3-12-8-11(2)18(23,10-20)17(22)24-9-13-4-6-19-7-5-14(15(13)19)25-16(12)21/h3-4,11,14-15,20,23H,5-10H2,1-2H3

> <INCHI_KEY>
BCJMNZRQJAVDLD-UHFFFAOYSA-N

> <FORMULA>
C18H25NO6

> <MOLECULAR_WEIGHT>
351.399

> <EXACT_MASS>
351.168187529

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
50

> <JCHEM_AVERAGE_POLARIZABILITY>
36.34117561085783

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-ethylidene-7-hydroxy-7-(hydroxymethyl)-6-methyl-2,9-dioxa-14-azatricyclo[9.5.1.0¹⁴,¹⁷]heptadec-11-ene-3,8-dione

> <ALOGPS_LOGP>
0.53

> <JCHEM_LOGP>
0.5969526486666659

> <ALOGPS_LOGS>
-1.59

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
14.971010053552853

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.442771664578194

> <JCHEM_PKA_STRONGEST_BASIC>
7.136049874699854

> <JCHEM_POLAR_SURFACE_AREA>
96.30000000000001

> <JCHEM_REFRACTIVITY>
90.95029999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.08e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-ethylidene-7-hydroxy-7-(hydroxymethyl)-6-methyl-2,9-dioxa-14-azatricyclo[9.5.1.0¹⁴,¹⁷]heptadec-11-ene-3,8-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0242585
     RDKit          3D
Usaramine
 50 52  0  0  0  0  0  0  0  0999 V2000
   -1.0393    4.3682    0.2549 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7115    3.1312   -0.1615 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1000    2.0572   -0.6679 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8978    0.8839   -1.0436 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9802   -0.1869    0.0319 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9133    0.2296    1.1198 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4652   -1.4306   -0.6693 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5718   -1.0147   -1.4561 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9728   -2.5130    0.2043 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0144   -2.0207    0.9871 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3662   -1.8612   -1.5756 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7146   -2.2000   -2.7614 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0435   -1.9282   -1.2696 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5964   -2.4874   -0.1757 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9941   -1.9540   -0.0507 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1697   -2.3581   -0.5126 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2462   -1.4344   -0.0713 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6218   -0.8508    1.1015 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1245    0.4699    1.3111 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9714    1.4068    1.0219 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2154    0.5599   -0.0200 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1106    1.0685   -0.5566 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3738    2.1318   -0.8326 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7260    3.3043   -1.2498 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2059   -0.7331    0.7160 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0600    4.1585    0.7726 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8850    5.0960   -0.5705 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6750    4.8836    1.0024 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8004    3.0853   -0.0510 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5484    0.3878   -1.9754 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9415    1.2042   -1.2462 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9559   -0.2682    0.4397 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7210   -0.4155    2.0263 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9636    0.2859    0.8321 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6305    1.2511    1.4753 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2889   -0.9320   -2.4188 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2235   -3.0393    0.8227 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4410   -3.2822   -0.4689 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8871   -2.0226    0.5128 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6176   -3.6066   -0.3465 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0564   -2.3945    0.7972 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3093   -3.2346   -1.1208 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1398   -2.0129    0.3064 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6159   -0.7427   -0.8098 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9642    0.7210    0.6297 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5205    0.6281    2.3497 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2750    2.3687    0.6108 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3427    1.4776    1.9387 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9891    0.4462   -0.8434 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6262   -0.6812    1.6602 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  3
  3  4  1  0
  4  5  1  0
  5  6  1  0
  5  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
  7 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  2  0
 21 25  1  0
 23  3  1  0
 25 15  1  0
 25 18  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  2 29  1  0
  4 30  1  0
  4 31  1  0
  5 32  1  0
  6 33  1  0
  6 34  1  0
  6 35  1  0
  8 36  1  0
  9 37  1  0
  9 38  1  0
 10 39  1  0
 14 40  1  0
 14 41  1  0
 16 42  1  0
 17 43  1  0
 17 44  1  0
 19 45  1  0
 19 46  1  0
 20 47  1  0
 20 48  1  0
 21 49  1  0
 25 50  1  0
M  END

HEADER    PROTEIN                                 17-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-APR-15         0                                  
HETATM    1  C   UNK     0      12.639   5.800   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      11.167   5.348   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      10.823   3.846   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      11.951   2.798   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      11.608   1.297   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      10.136   0.844   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      12.736   0.249   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      13.572   1.542   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      14.155  -0.350   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      15.383   0.579   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      12.392  -1.252   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      13.520  -2.301   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0      10.920  -1.705   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       9.792  -0.657   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.320  -1.110   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       7.396  -2.341   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.939  -1.843   0.000  0.00  0.00           C+0
HETATM   18  N   UNK     0       5.963  -0.303   0.000  0.00  0.00           N+0
HETATM   19  C   UNK     0       5.077   0.957   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.002   2.189   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       7.536   1.440   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       9.008   1.892   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       9.351   3.394   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       8.223   4.442   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       7.192  -0.062   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   23                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8    9   11                                             
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9                                                            
CONECT   11    7   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   25                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   25                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22   25                                                  
CONECT   22   21   23                                                       
CONECT   23   22    3   24                                                  
CONECT   24   23                                                            
CONECT   25   21   15   18                                                  
MASTER        0    0    0    0    0    0    0    0   25    0   54    0
END

COMPND    HMDB0242334
HETATM    1  C1  UNL     1      -0.726   4.325  -1.208  1.00  0.00           C  
HETATM    2  C2  UNL     1      -1.478   3.301  -0.409  1.00  0.00           C  
HETATM    3  C3  UNL     1      -1.180   2.017  -0.451  1.00  0.00           C  
HETATM    4  C4  UNL     1      -1.986   1.089   0.377  1.00  0.00           C  
HETATM    5  C5  UNL     1      -2.498  -0.090  -0.389  1.00  0.00           C  
HETATM    6  C6  UNL     1      -4.021  -0.126  -0.452  1.00  0.00           C  
HETATM    7  C7  UNL     1      -1.983  -1.383   0.160  1.00  0.00           C  
HETATM    8  O1  UNL     1      -1.211  -1.152   1.270  1.00  0.00           O  
HETATM    9  C8  UNL     1      -3.100  -2.317   0.587  1.00  0.00           C  
HETATM   10  O2  UNL     1      -2.460  -3.486   1.053  1.00  0.00           O  
HETATM   11  C9  UNL     1      -1.255  -2.075  -0.937  1.00  0.00           C  
HETATM   12  O3  UNL     1      -1.999  -2.600  -1.836  1.00  0.00           O  
HETATM   13  O4  UNL     1       0.090  -2.196  -1.067  1.00  0.00           O  
HETATM   14  C10 UNL     1       1.044  -2.564  -0.126  1.00  0.00           C  
HETATM   15  C11 UNL     1       2.317  -1.850  -0.355  1.00  0.00           C  
HETATM   16  C12 UNL     1       3.398  -2.197  -1.049  1.00  0.00           C  
HETATM   17  C13 UNL     1       4.407  -1.062  -0.933  1.00  0.00           C  
HETATM   18  N1  UNL     1       3.497   0.019  -0.818  1.00  0.00           N  
HETATM   19  C14 UNL     1       3.890   1.184  -0.113  1.00  0.00           C  
HETATM   20  C15 UNL     1       2.523   1.715   0.366  1.00  0.00           C  
HETATM   21  C16 UNL     1       1.574   0.502   0.232  1.00  0.00           C  
HETATM   22  O5  UNL     1       0.815   0.563  -0.947  1.00  0.00           O  
HETATM   23  C17 UNL     1      -0.071   1.555  -1.308  1.00  0.00           C  
HETATM   24  O6  UNL     1       0.020   2.151  -2.443  1.00  0.00           O  
HETATM   25  C18 UNL     1       2.584  -0.560   0.200  1.00  0.00           C  
HETATM   26  H1  UNL     1       0.357   4.042  -1.111  1.00  0.00           H  
HETATM   27  H2  UNL     1      -1.098   4.255  -2.236  1.00  0.00           H  
HETATM   28  H3  UNL     1      -0.912   5.299  -0.738  1.00  0.00           H  
HETATM   29  H4  UNL     1      -2.307   3.608   0.236  1.00  0.00           H  
HETATM   30  H5  UNL     1      -2.882   1.618   0.775  1.00  0.00           H  
HETATM   31  H6  UNL     1      -1.434   0.745   1.270  1.00  0.00           H  
HETATM   32  H7  UNL     1      -2.180   0.075  -1.461  1.00  0.00           H  
HETATM   33  H8  UNL     1      -4.311  -0.859  -1.214  1.00  0.00           H  
HETATM   34  H9  UNL     1      -4.479  -0.301   0.530  1.00  0.00           H  
HETATM   35  H10 UNL     1      -4.383   0.867  -0.829  1.00  0.00           H  
HETATM   36  H11 UNL     1      -1.702  -1.202   2.130  1.00  0.00           H  
HETATM   37  H12 UNL     1      -3.728  -2.575  -0.279  1.00  0.00           H  
HETATM   38  H13 UNL     1      -3.656  -1.922   1.454  1.00  0.00           H  
HETATM   39  H14 UNL     1      -2.729  -4.281   0.528  1.00  0.00           H  
HETATM   40  H15 UNL     1       1.166  -3.685  -0.226  1.00  0.00           H  
HETATM   41  H16 UNL     1       0.693  -2.453   0.942  1.00  0.00           H  
HETATM   42  H17 UNL     1       3.594  -3.100  -1.615  1.00  0.00           H  
HETATM   43  H18 UNL     1       5.060  -1.040  -1.825  1.00  0.00           H  
HETATM   44  H19 UNL     1       4.958  -1.262   0.005  1.00  0.00           H  
HETATM   45  H20 UNL     1       4.505   0.968   0.787  1.00  0.00           H  
HETATM   46  H21 UNL     1       4.398   1.940  -0.744  1.00  0.00           H  
HETATM   47  H22 UNL     1       2.238   2.489  -0.377  1.00  0.00           H  
HETATM   48  H23 UNL     1       2.580   2.074   1.393  1.00  0.00           H  
HETATM   49  H24 UNL     1       0.949   0.541   1.143  1.00  0.00           H  
HETATM   50  H25 UNL     1       3.108  -0.605   1.178  1.00  0.00           H  
CONECT    1    2   26   27   28
CONECT    2    3    3   29
CONECT    3    4   23
CONECT    4    5   30   31
CONECT    5    6    7   32
CONECT    6   33   34   35
CONECT    7    8    9   11
CONECT    8   36
CONECT    9   10   37   38
CONECT   10   39
CONECT   11   12   12   13
CONECT   13   14
CONECT   14   15   40   41
CONECT   15   16   16   25
CONECT   16   17   42
CONECT   17   18   43   44
CONECT   18   19   25
CONECT   19   20   45   46
CONECT   20   21   47   48
CONECT   21   22   25   49
CONECT   22   23
CONECT   23   24   24
CONECT   25   50
END

HMDB0242585
     RDKit          3D
Usaramine
 50 52  0  0  0  0  0  0  0  0999 V2000
   -1.0393    4.3682    0.2549 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7115    3.1312   -0.1615 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1000    2.0572   -0.6679 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8978    0.8839   -1.0436 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9802   -0.1869    0.0319 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9133    0.2296    1.1198 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4652   -1.4306   -0.6693 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5718   -1.0147   -1.4561 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9728   -2.5130    0.2043 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0144   -2.0207    0.9871 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3662   -1.8612   -1.5756 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7146   -2.2000   -2.7614 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0435   -1.9282   -1.2696 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5964   -2.4874   -0.1757 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9941   -1.9540   -0.0507 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1697   -2.3581   -0.5126 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2462   -1.4344   -0.0713 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6218   -0.8508    1.1015 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1245    0.4699    1.3111 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9714    1.4068    1.0219 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2154    0.5599   -0.0200 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1106    1.0685   -0.5566 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3738    2.1318   -0.8326 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7260    3.3043   -1.2498 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2059   -0.7331    0.7160 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0600    4.1585    0.7726 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8850    5.0960   -0.5705 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6750    4.8836    1.0024 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8004    3.0853   -0.0510 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5484    0.3878   -1.9754 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9415    1.2042   -1.2462 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9559   -0.2682    0.4397 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7210   -0.4155    2.0263 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9636    0.2859    0.8321 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6305    1.2511    1.4753 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2889   -0.9320   -2.4188 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2235   -3.0393    0.8227 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4410   -3.2822   -0.4689 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8871   -2.0226    0.5128 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6176   -3.6066   -0.3465 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0564   -2.3945    0.7972 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3093   -3.2346   -1.1208 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1398   -2.0129    0.3064 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6159   -0.7427   -0.8098 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9642    0.7210    0.6297 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5205    0.6281    2.3497 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2750    2.3687    0.6108 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3427    1.4776    1.9387 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9891    0.4462   -0.8434 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6262   -0.6812    1.6602 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  3
  3  4  1  0
  4  5  1  0
  5  6  1  0
  5  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
  7 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  2  0
 21 25  1  0
 23  3  1  0
 25 15  1  0
 25 18  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  2 29  1  0
  4 30  1  0
  4 31  1  0
  5 32  1  0
  6 33  1  0
  6 34  1  0
  6 35  1  0
  8 36  1  0
  9 37  1  0
  9 38  1  0
 10 39  1  0
 14 40  1  0
 14 41  1  0
 16 42  1  0
 17 43  1  0
 17 44  1  0
 19 45  1  0
 19 46  1  0
 20 47  1  0
 20 48  1  0
 21 49  1  0
 25 50  1  0
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
Retrorsine, (15E)-isomer	MeSH
Retrorsine	MeSH
Retrorsine hydrochloride	MeSH
Usaramine	MeSH

Chemical Formula

C₁₈H₂₅NO₆

Average Molecular Weight

351.399

Monoisotopic Molecular Weight

351.168187529

IUPAC Name

4-ethylidene-7-hydroxy-7-(hydroxymethyl)-6-methyl-2,9-dioxa-14-azatricyclo[9.5.1.0¹⁴,¹⁷]heptadec-11-ene-3,8-dione

Traditional Name

4-ethylidene-7-hydroxy-7-(hydroxymethyl)-6-methyl-2,9-dioxa-14-azatricyclo[9.5.1.0¹⁴,¹⁷]heptadec-11-ene-3,8-dione

CAS Registry Number

Not Available

SMILES

CC=C1CC(C)C(O)(CO)C(=O)OCC2=CCN3CCC(OC1=O)C23

InChI Identifier

InChI=1S/C18H25NO6/c1-3-12-8-11(2)18(23,10-20)17(22)24-9-13-4-6-19-7-5-14(15(13)19)25-16(12)21/h3-4,11,14-15,20,23H,5-10H2,1-2H3

InChI Key

BCJMNZRQJAVDLD-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as macrolides and analogues. These are organic compounds containing a lactone ring of at least twelve members.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Macrolides and analogues

Sub Class

Not Available

Direct Parent

Macrolides and analogues

Alternative Parents

Substituents

Senecionan-skeleton
Macrolide
Alkaloid or derivatives
Pyrrolizine
Dicarboxylic acid or derivatives
N-alkylpyrrolidine
Pyrrolidine
Pyrroline
Tertiary alcohol
Alpha,beta-unsaturated carboxylic ester
Enoate ester
1,2-diol
Amino acid or derivatives
Carboxylic acid ester
Lactone
Tertiary amine
Tertiary aliphatic amine
Carboxylic acid derivative
Oxacycle
Azacycle
Organoheterocyclic compound
Organic oxide
Primary alcohol
Organooxygen compound
Organonitrogen compound
Organopnictogen compound
Organic nitrogen compound
Organic oxygen compound
Carbonyl group
Hydrocarbon derivative
Amine
Alcohol
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Process

Not Available

Role

Not Available

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	0.53	ALOGPS
logP	0.6	ChemAxon
logS	-1.6	ALOGPS
pKa (Strongest Acidic)	11.44	ChemAxon
pKa (Strongest Basic)	7.14	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	1	ChemAxon
Refractivity	90.95 m³·mol⁻¹	ChemAxon
Polarizability	36.34 Å³	ChemAxon
Number of Rings	3	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
DeepCCS	[M-2H]-	210.932	30932474
DeepCCS	[M+Na]+	186.159	30932474
AllCCS	[M+H]+	181.9	32859911
AllCCS	[M+H-H2O]+	179.0	32859911
AllCCS	[M+NH4]+	184.6	32859911
AllCCS	[M+Na]+	185.4	32859911
AllCCS	[M-H]-	183.4	32859911
AllCCS	[M+Na-2H]-	183.6	32859911
AllCCS	[M+HCOO]-	183.9	32859911

Predicted Kovats Retention Indices

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
(1R,4E,6S,7S,17R)-4-Ethylidene-7-hydroxy-7-(hydroxymethyl)-6-methyl-2,9-dioxa-14-azatricyclo[9.5.1.014,17]heptadec-11-ene-3,8-dione,1TMS,isomer #1	CC=C1CC(C)C(CO)(O[Si](C)(C)C)C(=O)OCC2=CCN3CCC(OC1=O)C23	2983.9	Semi standard non polar	33892256
(1R,4E,6S,7S,17R)-4-Ethylidene-7-hydroxy-7-(hydroxymethyl)-6-methyl-2,9-dioxa-14-azatricyclo[9.5.1.014,17]heptadec-11-ene-3,8-dione,1TMS,isomer #1	CC=C1CC(C)C(CO)(O[Si](C)(C)C)C(=O)OCC2=CCN3CCC(OC1=O)C23	2683.4	Standard non polar	33892256
(1R,4E,6S,7S,17R)-4-Ethylidene-7-hydroxy-7-(hydroxymethyl)-6-methyl-2,9-dioxa-14-azatricyclo[9.5.1.014,17]heptadec-11-ene-3,8-dione,1TMS,isomer #1	CC=C1CC(C)C(CO)(O[Si](C)(C)C)C(=O)OCC2=CCN3CCC(OC1=O)C23	3948.3	Standard polar	33892256
(1R,4E,6S,7S,17R)-4-Ethylidene-7-hydroxy-7-(hydroxymethyl)-6-methyl-2,9-dioxa-14-azatricyclo[9.5.1.014,17]heptadec-11-ene-3,8-dione,1TMS,isomer #2	CC=C1CC(C)C(O)(CO[Si](C)(C)C)C(=O)OCC2=CCN3CCC(OC1=O)C23	2910.8	Semi standard non polar	33892256
(1R,4E,6S,7S,17R)-4-Ethylidene-7-hydroxy-7-(hydroxymethyl)-6-methyl-2,9-dioxa-14-azatricyclo[9.5.1.014,17]heptadec-11-ene-3,8-dione,1TMS,isomer #2	CC=C1CC(C)C(O)(CO[Si](C)(C)C)C(=O)OCC2=CCN3CCC(OC1=O)C23	2694.2	Standard non polar	33892256
(1R,4E,6S,7S,17R)-4-Ethylidene-7-hydroxy-7-(hydroxymethyl)-6-methyl-2,9-dioxa-14-azatricyclo[9.5.1.014,17]heptadec-11-ene-3,8-dione,1TMS,isomer #2	CC=C1CC(C)C(O)(CO[Si](C)(C)C)C(=O)OCC2=CCN3CCC(OC1=O)C23	3922.1	Standard polar	33892256
(1R,4E,6S,7S,17R)-4-Ethylidene-7-hydroxy-7-(hydroxymethyl)-6-methyl-2,9-dioxa-14-azatricyclo[9.5.1.014,17]heptadec-11-ene-3,8-dione,2TMS,isomer #1	CC=C1CC(C)C(CO[Si](C)(C)C)(O[Si](C)(C)C)C(=O)OCC2=CCN3CCC(OC1=O)C23	3010.1	Semi standard non polar	33892256
(1R,4E,6S,7S,17R)-4-Ethylidene-7-hydroxy-7-(hydroxymethyl)-6-methyl-2,9-dioxa-14-azatricyclo[9.5.1.014,17]heptadec-11-ene-3,8-dione,2TMS,isomer #1	CC=C1CC(C)C(CO[Si](C)(C)C)(O[Si](C)(C)C)C(=O)OCC2=CCN3CCC(OC1=O)C23	2799.9	Standard non polar	33892256
(1R,4E,6S,7S,17R)-4-Ethylidene-7-hydroxy-7-(hydroxymethyl)-6-methyl-2,9-dioxa-14-azatricyclo[9.5.1.014,17]heptadec-11-ene-3,8-dione,2TMS,isomer #1	CC=C1CC(C)C(CO[Si](C)(C)C)(O[Si](C)(C)C)C(=O)OCC2=CCN3CCC(OC1=O)C23	3804.0	Standard polar	33892256
(1R,4E,6S,7S,17R)-4-Ethylidene-7-hydroxy-7-(hydroxymethyl)-6-methyl-2,9-dioxa-14-azatricyclo[9.5.1.014,17]heptadec-11-ene-3,8-dione,1TBDMS,isomer #1	CC=C1CC(C)C(CO)(O[Si](C)(C)C(C)(C)C)C(=O)OCC2=CCN3CCC(OC1=O)C23	3203.2	Semi standard non polar	33892256
(1R,4E,6S,7S,17R)-4-Ethylidene-7-hydroxy-7-(hydroxymethyl)-6-methyl-2,9-dioxa-14-azatricyclo[9.5.1.014,17]heptadec-11-ene-3,8-dione,1TBDMS,isomer #1	CC=C1CC(C)C(CO)(O[Si](C)(C)C(C)(C)C)C(=O)OCC2=CCN3CCC(OC1=O)C23	2934.3	Standard non polar	33892256
(1R,4E,6S,7S,17R)-4-Ethylidene-7-hydroxy-7-(hydroxymethyl)-6-methyl-2,9-dioxa-14-azatricyclo[9.5.1.014,17]heptadec-11-ene-3,8-dione,1TBDMS,isomer #1	CC=C1CC(C)C(CO)(O[Si](C)(C)C(C)(C)C)C(=O)OCC2=CCN3CCC(OC1=O)C23	4055.3	Standard polar	33892256
(1R,4E,6S,7S,17R)-4-Ethylidene-7-hydroxy-7-(hydroxymethyl)-6-methyl-2,9-dioxa-14-azatricyclo[9.5.1.014,17]heptadec-11-ene-3,8-dione,1TBDMS,isomer #2	CC=C1CC(C)C(O)(CO[Si](C)(C)C(C)(C)C)C(=O)OCC2=CCN3CCC(OC1=O)C23	3134.7	Semi standard non polar	33892256
(1R,4E,6S,7S,17R)-4-Ethylidene-7-hydroxy-7-(hydroxymethyl)-6-methyl-2,9-dioxa-14-azatricyclo[9.5.1.014,17]heptadec-11-ene-3,8-dione,1TBDMS,isomer #2	CC=C1CC(C)C(O)(CO[Si](C)(C)C(C)(C)C)C(=O)OCC2=CCN3CCC(OC1=O)C23	2939.8	Standard non polar	33892256
(1R,4E,6S,7S,17R)-4-Ethylidene-7-hydroxy-7-(hydroxymethyl)-6-methyl-2,9-dioxa-14-azatricyclo[9.5.1.014,17]heptadec-11-ene-3,8-dione,1TBDMS,isomer #2	CC=C1CC(C)C(O)(CO[Si](C)(C)C(C)(C)C)C(=O)OCC2=CCN3CCC(OC1=O)C23	4060.6	Standard polar	33892256
(1R,4E,6S,7S,17R)-4-Ethylidene-7-hydroxy-7-(hydroxymethyl)-6-methyl-2,9-dioxa-14-azatricyclo[9.5.1.014,17]heptadec-11-ene-3,8-dione,2TBDMS,isomer #1	CC=C1CC(C)C(CO[Si](C)(C)C(C)(C)C)(O[Si](C)(C)C(C)(C)C)C(=O)OCC2=CCN3CCC(OC1=O)C23	3435.4	Semi standard non polar	33892256
(1R,4E,6S,7S,17R)-4-Ethylidene-7-hydroxy-7-(hydroxymethyl)-6-methyl-2,9-dioxa-14-azatricyclo[9.5.1.014,17]heptadec-11-ene-3,8-dione,2TBDMS,isomer #1	CC=C1CC(C)C(CO[Si](C)(C)C(C)(C)C)(O[Si](C)(C)C(C)(C)C)C(=O)OCC2=CCN3CCC(OC1=O)C23	3264.1	Standard non polar	33892256
(1R,4E,6S,7S,17R)-4-Ethylidene-7-hydroxy-7-(hydroxymethyl)-6-methyl-2,9-dioxa-14-azatricyclo[9.5.1.014,17]heptadec-11-ene-3,8-dione,2TBDMS,isomer #1	CC=C1CC(C)C(CO[Si](C)(C)C(C)(C)C)(O[Si](C)(C)C(C)(C)C)C(=O)OCC2=CCN3CCC(OC1=O)C23	3936.3	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - (1R,4E,6S,7S,17R)-4-Ethylidene-7-hydroxy-7-(hydroxymethyl)-6-methyl-2,9-dioxa-14-azatricyclo[9.5.1.014,17]heptadec-11-ene-3,8-dione GC-MS (Non-derivatized) - 70eV, Positive	splash10-001i-3009000000-c833a2bf3eb8c90047f2	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (1R,4E,6S,7S,17R)-4-Ethylidene-7-hydroxy-7-(hydroxymethyl)-6-methyl-2,9-dioxa-14-azatricyclo[9.5.1.014,17]heptadec-11-ene-3,8-dione GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (1R,4E,6S,7S,17R)-4-Ethylidene-7-hydroxy-7-(hydroxymethyl)-6-methyl-2,9-dioxa-14-azatricyclo[9.5.1.014,17]heptadec-11-ene-3,8-dione GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (1R,4E,6S,7S,17R)-4-Ethylidene-7-hydroxy-7-(hydroxymethyl)-6-methyl-2,9-dioxa-14-azatricyclo[9.5.1.014,17]heptadec-11-ene-3,8-dione GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (1R,4E,6S,7S,17R)-4-Ethylidene-7-hydroxy-7-(hydroxymethyl)-6-methyl-2,9-dioxa-14-azatricyclo[9.5.1.014,17]heptadec-11-ene-3,8-dione GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (1R,4E,6S,7S,17R)-4-Ethylidene-7-hydroxy-7-(hydroxymethyl)-6-methyl-2,9-dioxa-14-azatricyclo[9.5.1.014,17]heptadec-11-ene-3,8-dione GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (1R,4E,6S,7S,17R)-4-Ethylidene-7-hydroxy-7-(hydroxymethyl)-6-methyl-2,9-dioxa-14-azatricyclo[9.5.1.014,17]heptadec-11-ene-3,8-dione GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - (1R,4E,6S,7S,17R)-4-Ethylidene-7-hydroxy-7-(hydroxymethyl)-6-methyl-2,9-dioxa-14-azatricyclo[9.5.1.014,17]heptadec-11-ene-3,8-dione 6V, Positive-QTOF	splash10-0udi-0009000000-68619703f6a76e56a2e4	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - (1R,4E,6S,7S,17R)-4-Ethylidene-7-hydroxy-7-(hydroxymethyl)-6-methyl-2,9-dioxa-14-azatricyclo[9.5.1.014,17]heptadec-11-ene-3,8-dione 10V, Positive-QTOF	splash10-0udi-0009000000-c2e13f46e427c67d54f1	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - (1R,4E,6S,7S,17R)-4-Ethylidene-7-hydroxy-7-(hydroxymethyl)-6-methyl-2,9-dioxa-14-azatricyclo[9.5.1.014,17]heptadec-11-ene-3,8-dione 20V, Positive-QTOF	splash10-0udi-0109000000-9e1b1771da7232c86120	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - (1R,4E,6S,7S,17R)-4-Ethylidene-7-hydroxy-7-(hydroxymethyl)-6-methyl-2,9-dioxa-14-azatricyclo[9.5.1.014,17]heptadec-11-ene-3,8-dione 40V, Positive-QTOF	splash10-00di-0900000000-eca870f83e3b56e09c3a	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (1R,4E,6S,7S,17R)-4-Ethylidene-7-hydroxy-7-(hydroxymethyl)-6-methyl-2,9-dioxa-14-azatricyclo[9.5.1.014,17]heptadec-11-ene-3,8-dione 10V, Positive-QTOF	splash10-0udi-0009000000-e1a56fac03732a251e54	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (1R,4E,6S,7S,17R)-4-Ethylidene-7-hydroxy-7-(hydroxymethyl)-6-methyl-2,9-dioxa-14-azatricyclo[9.5.1.014,17]heptadec-11-ene-3,8-dione 20V, Positive-QTOF	splash10-0udi-0009000000-752955825b811f4b40b0	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (1R,4E,6S,7S,17R)-4-Ethylidene-7-hydroxy-7-(hydroxymethyl)-6-methyl-2,9-dioxa-14-azatricyclo[9.5.1.014,17]heptadec-11-ene-3,8-dione 40V, Positive-QTOF	splash10-0udi-0009000000-e5da015c5edf810c1bb1	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (1R,4E,6S,7S,17R)-4-Ethylidene-7-hydroxy-7-(hydroxymethyl)-6-methyl-2,9-dioxa-14-azatricyclo[9.5.1.014,17]heptadec-11-ene-3,8-dione 10V, Negative-QTOF	splash10-0udi-0009000000-a7d25e157fa82ae07948	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (1R,4E,6S,7S,17R)-4-Ethylidene-7-hydroxy-7-(hydroxymethyl)-6-methyl-2,9-dioxa-14-azatricyclo[9.5.1.014,17]heptadec-11-ene-3,8-dione 20V, Negative-QTOF	splash10-0v4i-0009000000-62ccf65d51f0492d50d1	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (1R,4E,6S,7S,17R)-4-Ethylidene-7-hydroxy-7-(hydroxymethyl)-6-methyl-2,9-dioxa-14-azatricyclo[9.5.1.014,17]heptadec-11-ene-3,8-dione 40V, Negative-QTOF	splash10-0udi-0009000000-627b22a11453e593166b	2021-10-12	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	31557052	details

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

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

267891

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

Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]

Showing metabocard for (1R,4E,6S,7S,17R)-4-Ethylidene-7-hydroxy-7-(hydroxymethyl)-6-methyl-2,9-dioxa-14-azatricyclo[9.5.1.014,17]heptadec-11-ene-3,8-dione (HMDB0242334)

MOL for HMDB0242334 ((1R,4E,6S,7S,17R)-4-Ethylidene-7-hydroxy-7-(hydroxymethyl)-6-methyl-2,9-dioxa-14-azatricyclo[9.5.1.014,17]heptadec-11-ene-3,8-dione)

3D MOL for HMDB0242334 ((1R,4E,6S,7S,17R)-4-Ethylidene-7-hydroxy-7-(hydroxymethyl)-6-methyl-2,9-dioxa-14-azatricyclo[9.5.1.014,17]heptadec-11-ene-3,8-dione)

3D SDF for HMDB0242334 ((1R,4E,6S,7S,17R)-4-Ethylidene-7-hydroxy-7-(hydroxymethyl)-6-methyl-2,9-dioxa-14-azatricyclo[9.5.1.014,17]heptadec-11-ene-3,8-dione)

3D-SDF for HMDB0242334 ((1R,4E,6S,7S,17R)-4-Ethylidene-7-hydroxy-7-(hydroxymethyl)-6-methyl-2,9-dioxa-14-azatricyclo[9.5.1.014,17]heptadec-11-ene-3,8-dione)

PDB for HMDB0242334 ((1R,4E,6S,7S,17R)-4-Ethylidene-7-hydroxy-7-(hydroxymethyl)-6-methyl-2,9-dioxa-14-azatricyclo[9.5.1.014,17]heptadec-11-ene-3,8-dione)

3D PDB for HMDB0242334 ((1R,4E,6S,7S,17R)-4-Ethylidene-7-hydroxy-7-(hydroxymethyl)-6-methyl-2,9-dioxa-14-azatricyclo[9.5.1.014,17]heptadec-11-ene-3,8-dione)

SMILES for HMDB0242334 ((1R,4E,6S,7S,17R)-4-Ethylidene-7-hydroxy-7-(hydroxymethyl)-6-methyl-2,9-dioxa-14-azatricyclo[9.5.1.014,17]heptadec-11-ene-3,8-dione)

INCHI for HMDB0242334 ((1R,4E,6S,7S,17R)-4-Ethylidene-7-hydroxy-7-(hydroxymethyl)-6-methyl-2,9-dioxa-14-azatricyclo[9.5.1.014,17]heptadec-11-ene-3,8-dione)

Structure for HMDB0242334 ((1R,4E,6S,7S,17R)-4-Ethylidene-7-hydroxy-7-(hydroxymethyl)-6-methyl-2,9-dioxa-14-azatricyclo[9.5.1.014,17]heptadec-11-ene-3,8-dione)

3D Structure for HMDB0242334 ((1R,4E,6S,7S,17R)-4-Ethylidene-7-hydroxy-7-(hydroxymethyl)-6-methyl-2,9-dioxa-14-azatricyclo[9.5.1.014,17]heptadec-11-ene-3,8-dione)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra