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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2021-09-23 17:11:10 UTC

Update Date

2021-09-23 17:11:10 UTC

HMDB ID

HMDB0302359

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Cynaustine

Description

Cynaustine belongs to alkaloids and derivatives class of compounds. Those are naturally occurring chemical compounds that contain mostly basic nitrogen atoms. This group also includes some related compounds with neutral and even weakly acidic propertiesand is 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. Cynaustine is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Cynaustine can be found in borage, which makes cynaustine a potential biomarker for the consumption of this food product.

Structure

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

HMDB0302359
     RDKit          3D
Cynaustine
 47 47  0  0  0  0  0  0  0  0999 V2000
    4.3187    1.1333    0.9480 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8511    0.7694    0.8205 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3580   -0.1624    1.8674 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6141    0.3365   -0.5938 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.9511    1.4554   -1.3929 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1887    0.0311   -0.8378 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5117    0.7360   -1.6233 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5617   -1.0296   -0.2160 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7989   -1.2658   -0.4830 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6858   -0.1633   -0.0500 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3368    0.9765    0.5464 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6089    1.7800    0.7889 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4704    0.6586    1.0220 N   0  0  0  0  0  4  0  0  0  0  0  0
   -4.8564    0.7970    0.8538 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2434   -0.6668    0.5524 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9416   -1.3070    0.0264 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1305   -0.0964   -0.2026 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5301   -0.7907   -0.9808 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.4376   -1.0009   -2.4772 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3116   -1.9539   -0.2932 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 Cl  0  0  0  0  0 15  0  0  0  0  0  0
    4.7462    1.4571   -0.0085 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4328    1.8684    1.7690 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8389    0.1913    1.2551 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3005    1.7496    0.9871 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1291   -1.1534    1.4659 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4179    0.2310    2.3424 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0701   -0.2444    2.7401 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3585    2.1872   -1.0394 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9555   -1.4001   -1.5824 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0808   -2.2428   -0.0286 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3650    1.3396    0.8452 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8872    2.2633   -0.1483 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5006    2.4358    1.6545 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2205    0.0779    1.8248 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3434    1.1355    1.8005 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1365    1.4072   -0.0040 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4876   -1.1087    1.5410 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0436   -0.7287   -0.1836 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1781   -1.8201   -0.9401 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5031   -1.9769    0.7638 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4535    0.4682   -1.0998 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5764   -0.4342   -0.7522 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8310   -0.2153   -2.9324 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0627   -2.0124   -2.6437 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4449   -0.9457   -2.9439 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3845   -2.7663   -0.8864 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  6
  4  6  1  0
  6  7  2  0
  6  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  1  0
 15 16  1  0
 16 17  1  0
  4 18  1  0
 18 19  1  0
 18 20  1  0
 17 10  1  0
 17 13  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  2 25  1  0
  3 26  1  0
  3 27  1  0
  3 28  1  0
  5 29  1  0
  9 30  1  0
  9 31  1  0
 11 32  1  0
 12 33  1  0
 12 34  1  0
 13 35  1  0
 14 36  1  0
 14 37  1  0
 15 38  1  0
 15 39  1  0
 16 40  1  0
 16 41  1  0
 17 42  1  6
 18 43  1  6
 19 44  1  0
 19 45  1  0
 19 46  1  0
 20 47  1  0
M  CHG  2  13   1  21  -1
M  END


  Mrv0541 02241221232D          

 21 21  0  0  1  0            999 V2000
   -0.6449   -0.4795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4375   -0.2507    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6357    0.5502    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.4365    0.3520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0085    0.9465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6653   -0.4406    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8348    0.7483    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6060    1.5410    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2628    0.1539    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5381    0.3520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1101   -0.2425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9654   -1.0547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6931   -1.4433    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2876   -0.8712    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    1.9273   -0.1291    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5218    0.4429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2495    0.0543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1048   -0.7579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8338    1.3510    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0320   -0.8227    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4888    0.0000    0.0000 Cl  0  5  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  0  0  0  0
  4  5  1  0  0  0  0
  4  6  1  0  0  0  0
  3  7  1  6  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 11 15  1  0  0  0  0
 15 16  1  1  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 14 18  1  0  0  0  0
  3 19  1  1  0  0  0
  2 20  1  6  0  0  0
M  CHG  2  14   1  21  -1
M  END
> <DATABASE_ID>
HMDB0302359

> <DATABASE_NAME>
hmdb

> <SMILES>
[Cl-].CC(C)[C@@](O)([C@H](C)O)C(=O)OCC1=CC[NH+]2CCC[C@H]12

> <INCHI_IDENTIFIER>
InChI=1S/C15H25NO4.ClH/c1-10(2)15(19,11(3)17)14(18)20-9-12-6-8-16-7-4-5-13(12)16;/h6,10-11,13,17,19H,4-5,7-9H2,1-3H3;1H/t11-,13+,15+;/m0./s1

> <INCHI_KEY>
IAZXZAXZQOMXBB-QWMUGUDESA-N

> <FORMULA>
C15H26ClNO4

> <MOLECULAR_WEIGHT>
319.824

> <EXACT_MASS>
319.155036032

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
31.198451911172942

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(7aR)-7-({[(2R)-2-hydroxy-2-[(1S)-1-hydroxyethyl]-3-methylbutanoyl]oxy}methyl)-1,2,3,4,5,7a-hexahydropyrrolizin-4-ium chloride

> <ALOGPS_LOGP>
-1.19

> <JCHEM_LOGP>
0.8565826193333326

> <ALOGPS_LOGS>
-2.94

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
14.8008992296846

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.3429961300961

> <JCHEM_PKA_STRONGEST_BASIC>
8.361161081322797

> <JCHEM_POLAR_SURFACE_AREA>
71.2

> <JCHEM_REFRACTIVITY>
87.64149999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.65e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(7aR)-1-({[(2R)-2-hydroxy-2-[(1S)-1-hydroxyethyl]-3-methylbutanoyl]oxy}methyl)-3,4,5,6,7,7a-hexahydropyrrolizin-4-ium chloride

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0302359
     RDKit          3D
Cynaustine
 47 47  0  0  0  0  0  0  0  0999 V2000
    4.3187    1.1333    0.9480 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8511    0.7694    0.8205 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3580   -0.1624    1.8674 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6141    0.3365   -0.5938 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.9511    1.4554   -1.3929 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1887    0.0311   -0.8378 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5117    0.7360   -1.6233 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5617   -1.0296   -0.2160 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7989   -1.2658   -0.4830 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6858   -0.1633   -0.0500 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3368    0.9765    0.5464 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6089    1.7800    0.7889 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4704    0.6586    1.0220 N   0  0  0  0  0  4  0  0  0  0  0  0
   -4.8564    0.7970    0.8538 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2434   -0.6668    0.5524 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9416   -1.3070    0.0264 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1305   -0.0964   -0.2026 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5301   -0.7907   -0.9808 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.4376   -1.0009   -2.4772 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3116   -1.9539   -0.2932 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 Cl  0  0  0  0  0 15  0  0  0  0  0  0
    4.7462    1.4571   -0.0085 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4328    1.8684    1.7690 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8389    0.1913    1.2551 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3005    1.7496    0.9871 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1291   -1.1534    1.4659 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4179    0.2310    2.3424 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0701   -0.2444    2.7401 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3585    2.1872   -1.0394 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9555   -1.4001   -1.5824 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0808   -2.2428   -0.0286 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3650    1.3396    0.8452 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8872    2.2633   -0.1483 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5006    2.4358    1.6545 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2205    0.0779    1.8248 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3434    1.1355    1.8005 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1365    1.4072   -0.0040 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4876   -1.1087    1.5410 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0436   -0.7287   -0.1836 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1781   -1.8201   -0.9401 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5031   -1.9769    0.7638 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4535    0.4682   -1.0998 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5764   -0.4342   -0.7522 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8310   -0.2153   -2.9324 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0627   -2.0124   -2.6437 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4449   -0.9457   -2.9439 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3845   -2.7663   -0.8864 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  6
  4  6  1  0
  6  7  2  0
  6  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  1  0
 15 16  1  0
 16 17  1  0
  4 18  1  0
 18 19  1  0
 18 20  1  0
 17 10  1  0
 17 13  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  2 25  1  0
  3 26  1  0
  3 27  1  0
  3 28  1  0
  5 29  1  0
  9 30  1  0
  9 31  1  0
 11 32  1  0
 12 33  1  0
 12 34  1  0
 13 35  1  0
 14 36  1  0
 14 37  1  0
 15 38  1  0
 15 39  1  0
 16 40  1  0
 16 41  1  0
 17 42  1  6
 18 43  1  6
 19 44  1  0
 19 45  1  0
 19 46  1  0
 20 47  1  0
M  CHG  2  13   1  21  -1
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      -1.204  -0.895   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.683  -0.468   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -3.053   1.027   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -4.548   0.657   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -5.616   1.767   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -4.975  -0.822   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.558   1.397   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -1.131   2.877   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0      -0.491   0.287   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       1.004   0.657   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.072  -0.453   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.802  -1.969   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.160  -2.694   0.000  0.00  0.00           C+0
HETATM   14  N   UNK     0       4.270  -1.626   0.000  0.00  0.00           N+1
HETATM   15  C   UNK     0       3.598  -0.241   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.707   0.827   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.066   0.101   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.796  -1.415   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -3.423   2.522   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      -3.793  -1.536   0.000  0.00  0.00           O+0
HETATM   21 Cl   UNK     0      10.246   0.000   0.000  0.00  0.00          Cl-1
CONECT    1    2                                                            
CONECT    2    1    3   20                                                  
CONECT    3    2    4    7   19                                             
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4                                                            
CONECT    7    3    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   15                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   18                                                  
CONECT   15   14   11   16                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   14                                                       
CONECT   19    3                                                            
CONECT   20    2                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   42    0
END

COMPND    HMDB0302359
HETATM    1  C1  UNL     1       4.319   1.133   0.948  1.00  0.00           C  
HETATM    2  C2  UNL     1       2.851   0.769   0.820  1.00  0.00           C  
HETATM    3  C3  UNL     1       2.358  -0.162   1.867  1.00  0.00           C  
HETATM    4  C4  UNL     1       2.614   0.337  -0.594  1.00  0.00           C  
HETATM    5  O1  UNL     1       2.951   1.455  -1.393  1.00  0.00           O  
HETATM    6  C5  UNL     1       1.189   0.031  -0.838  1.00  0.00           C  
HETATM    7  O2  UNL     1       0.512   0.736  -1.623  1.00  0.00           O  
HETATM    8  O3  UNL     1       0.562  -1.030  -0.216  1.00  0.00           O  
HETATM    9  C6  UNL     1      -0.799  -1.266  -0.483  1.00  0.00           C  
HETATM   10  C7  UNL     1      -1.686  -0.163  -0.050  1.00  0.00           C  
HETATM   11  C8  UNL     1      -1.337   0.976   0.546  1.00  0.00           C  
HETATM   12  C9  UNL     1      -2.609   1.780   0.789  1.00  0.00           C  
HETATM   13  N1  UNL     1      -3.470   0.659   1.022  1.00  0.00           N1+
HETATM   14  C10 UNL     1      -4.856   0.797   0.854  1.00  0.00           C  
HETATM   15  C11 UNL     1      -5.243  -0.667   0.552  1.00  0.00           C  
HETATM   16  C12 UNL     1      -3.942  -1.307   0.026  1.00  0.00           C  
HETATM   17  C13 UNL     1      -3.130  -0.096  -0.203  1.00  0.00           C  
HETATM   18  C14 UNL     1       3.530  -0.791  -0.981  1.00  0.00           C  
HETATM   19  C15 UNL     1       3.438  -1.001  -2.477  1.00  0.00           C  
HETATM   20  O4  UNL     1       3.312  -1.954  -0.293  1.00  0.00           O  
HETATM   21 CL1  UNL     1       0.000   0.000   0.000  1.00  0.00          CL1-
HETATM   22  H1  UNL     1       4.746   1.457  -0.008  1.00  0.00           H  
HETATM   23  H2  UNL     1       4.433   1.868   1.769  1.00  0.00           H  
HETATM   24  H3  UNL     1       4.839   0.191   1.255  1.00  0.00           H  
HETATM   25  H4  UNL     1       2.300   1.750   0.987  1.00  0.00           H  
HETATM   26  H5  UNL     1       2.129  -1.153   1.466  1.00  0.00           H  
HETATM   27  H6  UNL     1       1.418   0.231   2.342  1.00  0.00           H  
HETATM   28  H7  UNL     1       3.070  -0.244   2.740  1.00  0.00           H  
HETATM   29  H8  UNL     1       2.358   2.187  -1.039  1.00  0.00           H  
HETATM   30  H9  UNL     1      -0.955  -1.400  -1.582  1.00  0.00           H  
HETATM   31  H10 UNL     1      -1.081  -2.243  -0.029  1.00  0.00           H  
HETATM   32  H11 UNL     1      -0.365   1.340   0.845  1.00  0.00           H  
HETATM   33  H12 UNL     1      -2.887   2.263  -0.148  1.00  0.00           H  
HETATM   34  H13 UNL     1      -2.501   2.436   1.654  1.00  0.00           H  
HETATM   35  H14 UNL     1      -3.221   0.078   1.825  1.00  0.00           H  
HETATM   36  H15 UNL     1      -5.343   1.136   1.801  1.00  0.00           H  
HETATM   37  H16 UNL     1      -5.136   1.407  -0.004  1.00  0.00           H  
HETATM   38  H17 UNL     1      -5.488  -1.109   1.541  1.00  0.00           H  
HETATM   39  H18 UNL     1      -6.044  -0.729  -0.184  1.00  0.00           H  
HETATM   40  H19 UNL     1      -4.178  -1.820  -0.940  1.00  0.00           H  
HETATM   41  H20 UNL     1      -3.503  -1.977   0.764  1.00  0.00           H  
HETATM   42  H21 UNL     1      -3.454   0.468  -1.100  1.00  0.00           H  
HETATM   43  H22 UNL     1       4.576  -0.434  -0.752  1.00  0.00           H  
HETATM   44  H23 UNL     1       2.831  -0.215  -2.932  1.00  0.00           H  
HETATM   45  H24 UNL     1       3.063  -2.012  -2.644  1.00  0.00           H  
HETATM   46  H25 UNL     1       4.445  -0.946  -2.944  1.00  0.00           H  
HETATM   47  H26 UNL     1       3.385  -2.766  -0.886  1.00  0.00           H  
CONECT    1    2   22   23   24
CONECT    2    3    4   25
CONECT    3   26   27   28
CONECT    4    5    6   18
CONECT    5   29
CONECT    6    7    7    8
CONECT    8    9
CONECT    9   10   30   31
CONECT   10   11   11   17
CONECT   11   12   32
CONECT   12   13   33   34
CONECT   13   14   17   35
CONECT   14   15   36   37
CONECT   15   16   38   39
CONECT   16   17   40   41
CONECT   17   42
CONECT   18   19   20   43
CONECT   19   44   45   46
CONECT   20   47
END

HMDB0302359
     RDKit          3D
Cynaustine
 47 47  0  0  0  0  0  0  0  0999 V2000
    4.3187    1.1333    0.9480 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8511    0.7694    0.8205 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3580   -0.1624    1.8674 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6141    0.3365   -0.5938 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.9511    1.4554   -1.3929 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1887    0.0311   -0.8378 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5117    0.7360   -1.6233 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5617   -1.0296   -0.2160 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7989   -1.2658   -0.4830 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6858   -0.1633   -0.0500 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3368    0.9765    0.5464 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6089    1.7800    0.7889 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4704    0.6586    1.0220 N   0  0  0  0  0  4  0  0  0  0  0  0
   -4.8564    0.7970    0.8538 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2434   -0.6668    0.5524 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9416   -1.3070    0.0264 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1305   -0.0964   -0.2026 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5301   -0.7907   -0.9808 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.4376   -1.0009   -2.4772 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3116   -1.9539   -0.2932 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 Cl  0  0  0  0  0 15  0  0  0  0  0  0
    4.7462    1.4571   -0.0085 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4328    1.8684    1.7690 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8389    0.1913    1.2551 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3005    1.7496    0.9871 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1291   -1.1534    1.4659 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4179    0.2310    2.3424 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0701   -0.2444    2.7401 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3585    2.1872   -1.0394 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9555   -1.4001   -1.5824 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0808   -2.2428   -0.0286 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3650    1.3396    0.8452 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8872    2.2633   -0.1483 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5006    2.4358    1.6545 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2205    0.0779    1.8248 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3434    1.1355    1.8005 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1365    1.4072   -0.0040 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4876   -1.1087    1.5410 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0436   -0.7287   -0.1836 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1781   -1.8201   -0.9401 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5031   -1.9769    0.7638 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4535    0.4682   -1.0998 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5764   -0.4342   -0.7522 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8310   -0.2153   -2.9324 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0627   -2.0124   -2.6437 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4449   -0.9457   -2.9439 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3845   -2.7663   -0.8864 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  6
  4  6  1  0
  6  7  2  0
  6  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  1  0
 15 16  1  0
 16 17  1  0
  4 18  1  0
 18 19  1  0
 18 20  1  0
 17 10  1  0
 17 13  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  2 25  1  0
  3 26  1  0
  3 27  1  0
  3 28  1  0
  5 29  1  0
  9 30  1  0
  9 31  1  0
 11 32  1  0
 12 33  1  0
 12 34  1  0
 13 35  1  0
 14 36  1  0
 14 37  1  0
 15 38  1  0
 15 39  1  0
 16 40  1  0
 16 41  1  0
 17 42  1  6
 18 43  1  6
 19 44  1  0
 19 45  1  0
 19 46  1  0
 20 47  1  0
M  CHG  2  13   1  21  -1
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
[(7AR)-2,3,5,7a-tetrahydro-1H-pyrrolizin-7-yl]methyl (2R)-2-hydroxy-2-[(1S)-1-hydroxyethyl]-3-methylbutanoic acid hydrochloride	Generator

Chemical Formula

C₁₅H₂₆ClNO₄

Average Molecular Weight

319.824

Monoisotopic Molecular Weight

319.155036032

IUPAC Name

(7aR)-7-({[(2R)-2-hydroxy-2-[(1S)-1-hydroxyethyl]-3-methylbutanoyl]oxy}methyl)-1,2,3,4,5,7a-hexahydropyrrolizin-4-ium chloride

Traditional Name

(7aR)-1-({[(2R)-2-hydroxy-2-[(1S)-1-hydroxyethyl]-3-methylbutanoyl]oxy}methyl)-3,4,5,6,7,7a-hexahydropyrrolizin-4-ium chloride

CAS Registry Number

Not Available

SMILES

[Cl-].CC(C)[C@@](O)([C@H](C)O)C(=O)OCC1=CC[NH+]2CCC[C@H]12

InChI Identifier

InChI=1S/C15H25NO4.ClH/c1-10(2)15(19,11(3)17)14(18)20-9-12-6-8-16-7-4-5-13(12)16;/h6,10-11,13,17,19H,4-5,7-9H2,1-3H3;1H/t11-,13+,15+;/m0./s1

InChI Key

IAZXZAXZQOMXBB-QWMUGUDESA-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
Hydroxy acid
Fatty acyl
N-alkylpyrrolidine
Pyrrolidine
Pyrroline
Tertiary alcohol
1,2-diol
Amino acid or derivatives
Carboxylic acid ester
Secondary alcohol
Tertiary amine
Tertiary aliphatic amine
Organoheterocyclic compound
Azacycle
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Organic salt
Organooxygen compound
Organonitrogen compound
Organic oxide
Organopnictogen compound
Organic oxygen compound
Hydrocarbon derivative
Carbonyl group
Organic chloride salt
Alcohol
Organic nitrogen compound
Amine
Organic zwitterion
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Exogenous (HMDB: HMDB0302359)

Food

Herb and spice

Oilseed crop

Borage (FooDB: FOOD00026)

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	-1.2	ALOGPS
logP	0.86	ChemAxon
logS	-2.9	ALOGPS
pKa (Strongest Acidic)	11.34	ChemAxon
pKa (Strongest Basic)	8.36	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	71.2 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	87.64 m³·mol⁻¹	ChemAxon
Polarizability	31.2 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]+	195.594	32859911
AllCCS	[M+H-H2O]+	193.143	32859911
AllCCS	[M+Na]+	198.496	32859911
AllCCS	[M+NH4]+	197.85	32859911
AllCCS	[M-H]-	176.11	32859911
AllCCS	[M+Na-2H]-	176.893	32859911
AllCCS	[M+HCOO]-	177.876	32859911
DeepCCS	[M-2H]-	202.319	30932474
DeepCCS	[M+Na]+	177.151	30932474

Predicted Kovats Retention Indices

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Cynaustine,3TMS,isomer #1	CC(C)[C@](O[Si](C)(C)C)(C(=O)OCC1=CC[N+]2([Si](C)(C)C)CCC[C@H]12)[C@H](C)O[Si](C)(C)C	2303.7	Semi standard non polar	33892256
Cynaustine,3TMS,isomer #1	CC(C)[C@](O[Si](C)(C)C)(C(=O)OCC1=CC[N+]2([Si](C)(C)C)CCC[C@H]12)[C@H](C)O[Si](C)(C)C	2339.1	Standard non polar	33892256
Cynaustine,3TMS,isomer #1	CC(C)[C@](O[Si](C)(C)C)(C(=O)OCC1=CC[N+]2([Si](C)(C)C)CCC[C@H]12)[C@H](C)O[Si](C)(C)C	2776.6	Standard polar	33892256
Cynaustine,3TBDMS,isomer #1	CC(C)[C@](O[Si](C)(C)C(C)(C)C)(C(=O)OCC1=CC[N+]2([Si](C)(C)C(C)(C)C)CCC[C@H]12)[C@H](C)O[Si](C)(C)C(C)(C)C	2950.0	Semi standard non polar	33892256
Cynaustine,3TBDMS,isomer #1	CC(C)[C@](O[Si](C)(C)C(C)(C)C)(C(=O)OCC1=CC[N+]2([Si](C)(C)C(C)(C)C)CCC[C@H]12)[C@H](C)O[Si](C)(C)C(C)(C)C	2925.0	Standard non polar	33892256
Cynaustine,3TBDMS,isomer #1	CC(C)[C@](O[Si](C)(C)C(C)(C)C)(C(=O)OCC1=CC[N+]2([Si](C)(C)C(C)(C)C)CCC[C@H]12)[C@H](C)O[Si](C)(C)C(C)(C)C	3070.3	Standard polar	33892256

Spectra

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cynaustine 10V, Positive-QTOF	splash10-00di-0009000000-aeaa6a18fbdff1763fd2	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cynaustine 20V, Positive-QTOF	splash10-00di-0009000000-aeaa6a18fbdff1763fd2	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cynaustine 40V, Positive-QTOF	splash10-00di-0009000000-aeaa6a18fbdff1763fd2	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cynaustine 10V, Negative-QTOF	splash10-014i-0009000000-a91ce199ed3dfc96a1c5	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cynaustine 20V, Negative-QTOF	splash10-014i-0009000000-a91ce199ed3dfc96a1c5	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cynaustine 40V, Negative-QTOF	splash10-014i-0009000000-a91ce199ed3dfc96a1c5	2016-08-03	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

FDB004286

KNApSAcK ID

Not Available

Chemspider ID

26831

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

28846

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 Cynaustine (HMDB0302359)

MOL for HMDB0302359 (Cynaustine)

3D MOL for HMDB0302359 (Cynaustine)

3D SDF for HMDB0302359 (Cynaustine)

3D-SDF for HMDB0302359 (Cynaustine)

PDB for HMDB0302359 (Cynaustine)

3D PDB for HMDB0302359 (Cynaustine)

SMILES for HMDB0302359 (Cynaustine)

INCHI for HMDB0302359 (Cynaustine)

Structure for HMDB0302359 (Cynaustine)

3D Structure for HMDB0302359 (Cynaustine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Derivatized

MS/MS Spectra