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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2021-09-23 20:05:19 UTC

Update Date

2021-09-23 20:05:19 UTC

HMDB ID

HMDB0302721

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Pretazettine

Description

Pretazettine, also known as pretazettine hydrochloride, (6abeta,8beta)-isomer, is a member of the class of compounds known as tazettine-type amaryllidaceae alkaloids. Tazettine-type amaryllidaceae alkaloids are amaryllidaceae alkaloids derived from the haemanthamine-type alkaloids, which are characterized as a linkage between C6 and C11 by an oxygen atom to form a [3,4-g]benzopyran framework. Pretazettine is slightly soluble (in water) and a very weakly acidic compound (based on its pKa). Pretazettine can be found in lovage, which makes pretazettine a potential biomarker for the consumption of this food product.

Structure

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

HMDB0302721
     RDKit          3D
Pretazettine
 45 49  0  0  0  0  0  0  0  0999 V2000
    3.4532    2.6120   -1.8795 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2896    2.0990   -1.3686 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3597    0.7596   -1.0138 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5179   -0.0232   -1.9563 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4565   -0.7195   -1.6529 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0132   -0.7807   -0.2533 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1691    0.0355    0.0316 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0833    1.4100    0.0133 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1887    2.2277    0.2867 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3972    1.6334    0.5823 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4581    0.2430    0.5941 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3775   -0.5546    0.3268 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5782   -2.0384    0.3624 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.4966   -2.4151    1.7029 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5491   -2.6633   -0.3957 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4064   -2.2190    0.1388 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8583   -2.9043   -0.1301 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8529   -1.9732    0.3687 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4640   -2.4763    1.5900 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1678   -0.6985    0.6430 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0869    0.4648    0.4134 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3101    2.6550    0.8091 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7836    3.8776    0.3186 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3747    3.6005    0.3354 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3076    2.5479   -1.1647 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6956    2.1729   -2.8720 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2933    3.6953   -2.0553 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4220    0.4566   -1.2633 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8408    0.0018   -3.0094 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0847   -1.2546   -2.4210 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1852    1.9645   -0.2115 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4230   -0.2069    0.8301 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5237   -2.3497   -0.0927 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3520   -1.6585    2.3106 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5312   -2.1560    1.2610 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0260   -3.1988   -1.1773 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9334   -3.8565    0.4656 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4931   -1.6455    2.3179 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4511   -2.8902    1.3581 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7867   -3.2448    2.0204 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9052   -0.7306    1.7112 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7189    1.3115    1.0212 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0565    0.1743    0.9264 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0391    4.7426    0.9285 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1119    3.9726   -0.7506 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  6  5  1  6
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
 10 22  1  0
 22 23  1  0
 23 24  1  0
 21  3  1  0
 16  6  1  0
 20  6  1  0
 12  7  1  0
 24  9  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  3 28  1  6
  4 29  1  0
  5 30  1  0
  8 31  1  0
 11 32  1  0
 13 33  1  6
 14 34  1  0
 16 35  1  1
 17 36  1  0
 17 37  1  0
 19 38  1  0
 19 39  1  0
 19 40  1  0
 20 41  1  1
 21 42  1  0
 21 43  1  0
 23 44  1  0
 23 45  1  0
M  END


  Mrv0541 02241221432D          

 24 28  0  0  1  0            999 V2000
   -0.5727   -0.6026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0436   -0.0541    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0380    0.7669    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7176    1.0981    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2661    0.4819    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8495   -0.2302    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2579   -0.9471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0829   -0.9518    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4995   -0.2397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0487    0.3685    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4913   -1.6686    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3163   -1.6733    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0740    0.6488    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6226    0.0325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4305    0.1995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6899    0.9826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1414    1.5988    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3335    1.4319    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7849    2.0482    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9770    1.8813    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0444    2.8313    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5149    0.9779    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7654    0.1918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0952   -0.2893    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  2  6  1  0  0  0  0
  6  7  1  6  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  5 10  1  0  0  0  0
  8 11  1  1  0  0  0
 11 12  1  0  0  0  0
  5 13  1  1  0  0  0
 13 14  2  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  2  0  0  0  0
 13 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
  4 20  1  6  0  0  0
 19 21  1  1  0  0  0
 16 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 15 24  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0302721

> <DATABASE_NAME>
hmdb

> <SMILES>
CO[C@H]1C[C@@H]2N(C)C[C@@H]3O[C@@H](O)C4=CC5=C(OCO5)C=C4[C@@]23C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C18H21NO5/c1-19-8-16-18(4-3-10(21-2)5-15(18)19)12-7-14-13(22-9-23-14)6-11(12)17(20)24-16/h3-4,6-7,10,15-17,20H,5,8-9H2,1-2H3/t10-,15+,16+,17-,18+/m1/s1

> <INCHI_KEY>
KLJOYDMUWKSYBP-YNBLHMCPSA-N

> <FORMULA>
C18H21NO5

> <MOLECULAR_WEIGHT>
331.363

> <EXACT_MASS>
331.141972787

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
34.51890116487225

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,11R,13R,16S,18S)-18-methoxy-15-methyl-5,7,12-trioxa-15-azapentacyclo[11.7.0.0¹,¹⁶.0²,¹⁰.0⁴,⁸]icosa-2,4(8),9,19-tetraen-11-ol

> <ALOGPS_LOGP>
0.73

> <JCHEM_LOGP>
1.1046517213333338

> <ALOGPS_LOGS>
-2.13

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.538935798958123

> <JCHEM_PKA_STRONGEST_BASIC>
7.709644075241631

> <JCHEM_POLAR_SURFACE_AREA>
60.390000000000015

> <JCHEM_REFRACTIVITY>
86.88520000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.46e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
pretazettine

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0302721
     RDKit          3D
Pretazettine
 45 49  0  0  0  0  0  0  0  0999 V2000
    3.4532    2.6120   -1.8795 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2896    2.0990   -1.3686 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3597    0.7596   -1.0138 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5179   -0.0232   -1.9563 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4565   -0.7195   -1.6529 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0132   -0.7807   -0.2533 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1691    0.0355    0.0316 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0833    1.4100    0.0133 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1887    2.2277    0.2867 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3972    1.6334    0.5823 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4581    0.2430    0.5941 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3775   -0.5546    0.3268 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5782   -2.0384    0.3624 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.4966   -2.4151    1.7029 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5491   -2.6633   -0.3957 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4064   -2.2190    0.1388 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8583   -2.9043   -0.1301 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8529   -1.9732    0.3687 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4640   -2.4763    1.5900 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1678   -0.6985    0.6430 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0869    0.4648    0.4134 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3101    2.6550    0.8091 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7836    3.8776    0.3186 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3747    3.6005    0.3354 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3076    2.5479   -1.1647 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6956    2.1729   -2.8720 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2933    3.6953   -2.0553 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4220    0.4566   -1.2633 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8408    0.0018   -3.0094 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0847   -1.2546   -2.4210 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1852    1.9645   -0.2115 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4230   -0.2069    0.8301 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5237   -2.3497   -0.0927 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3520   -1.6585    2.3106 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5312   -2.1560    1.2610 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0260   -3.1988   -1.1773 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9334   -3.8565    0.4656 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4931   -1.6455    2.3179 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4511   -2.8902    1.3581 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7867   -3.2448    2.0204 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9052   -0.7306    1.7112 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7189    1.3115    1.0212 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0565    0.1743    0.9264 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0391    4.7426    0.9285 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1119    3.9726   -0.7506 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  6  5  1  6
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
 10 22  1  0
 22 23  1  0
 23 24  1  0
 21  3  1  0
 16  6  1  0
 20  6  1  0
 12  7  1  0
 24  9  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  3 28  1  6
  4 29  1  0
  5 30  1  0
  8 31  1  0
 11 32  1  0
 13 33  1  6
 14 34  1  0
 16 35  1  1
 17 36  1  0
 17 37  1  0
 19 38  1  0
 19 39  1  0
 19 40  1  0
 20 41  1  1
 21 42  1  0
 21 43  1  0
 23 44  1  0
 23 45  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      -1.069  -1.125   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0       0.081  -0.101   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0      -0.071   1.432   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.340   2.050   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.363   0.900   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.586  -0.430   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.348  -1.768   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.888  -1.777   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.666  -0.447   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.824   0.688   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       4.650  -3.115   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       6.190  -3.123   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.871   1.211   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.896   0.061   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.404   0.372   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.888   1.834   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.864   2.984   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.356   2.673   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.332   3.823   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       1.824   3.512   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       3.816   5.285   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       8.428   1.825   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       8.895   0.358   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       7.644  -0.540   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    6                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   20                                                  
CONECT    5    4    6   10   13                                             
CONECT    6    5    2    7                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   11                                                  
CONECT    9    8   10                                                       
CONECT   10    9    5                                                       
CONECT   11    8   12                                                       
CONECT   12   11                                                            
CONECT   13    5   14   18                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   24                                                  
CONECT   16   15   17   22                                                  
CONECT   17   16   18                                                       
CONECT   18   17   13   19                                                  
CONECT   19   18   20   21                                                  
CONECT   20   19    4                                                       
CONECT   21   19                                                            
CONECT   22   16   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   15                                                       
MASTER        0    0    0    0    0    0    0    0   24    0   56    0
END

COMPND    HMDB0302721
HETATM    1  C1  UNL     1       3.453   2.612  -1.880  1.00  0.00           C  
HETATM    2  O1  UNL     1       2.290   2.099  -1.369  1.00  0.00           O  
HETATM    3  C2  UNL     1       2.360   0.760  -1.014  1.00  0.00           C  
HETATM    4  C3  UNL     1       1.518  -0.023  -1.956  1.00  0.00           C  
HETATM    5  C4  UNL     1       0.457  -0.719  -1.653  1.00  0.00           C  
HETATM    6  C5  UNL     1      -0.013  -0.781  -0.253  1.00  0.00           C  
HETATM    7  C6  UNL     1      -1.169   0.036   0.032  1.00  0.00           C  
HETATM    8  C7  UNL     1      -1.083   1.410   0.013  1.00  0.00           C  
HETATM    9  C8  UNL     1      -2.189   2.228   0.287  1.00  0.00           C  
HETATM   10  C9  UNL     1      -3.397   1.633   0.582  1.00  0.00           C  
HETATM   11  C10 UNL     1      -3.458   0.243   0.594  1.00  0.00           C  
HETATM   12  C11 UNL     1      -2.378  -0.555   0.327  1.00  0.00           C  
HETATM   13  C12 UNL     1      -2.578  -2.038   0.362  1.00  0.00           C  
HETATM   14  O2  UNL     1      -2.497  -2.415   1.703  1.00  0.00           O  
HETATM   15  O3  UNL     1      -1.549  -2.663  -0.396  1.00  0.00           O  
HETATM   16  C13 UNL     1      -0.406  -2.219   0.139  1.00  0.00           C  
HETATM   17  C14 UNL     1       0.858  -2.904  -0.130  1.00  0.00           C  
HETATM   18  N1  UNL     1       1.853  -1.973   0.369  1.00  0.00           N  
HETATM   19  C15 UNL     1       2.464  -2.476   1.590  1.00  0.00           C  
HETATM   20  C16 UNL     1       1.168  -0.699   0.643  1.00  0.00           C  
HETATM   21  C17 UNL     1       2.087   0.465   0.413  1.00  0.00           C  
HETATM   22  O4  UNL     1      -4.310   2.655   0.809  1.00  0.00           O  
HETATM   23  C18 UNL     1      -3.784   3.878   0.319  1.00  0.00           C  
HETATM   24  O5  UNL     1      -2.375   3.600   0.335  1.00  0.00           O  
HETATM   25  H1  UNL     1       4.308   2.548  -1.165  1.00  0.00           H  
HETATM   26  H2  UNL     1       3.696   2.173  -2.872  1.00  0.00           H  
HETATM   27  H3  UNL     1       3.293   3.695  -2.055  1.00  0.00           H  
HETATM   28  H4  UNL     1       3.422   0.457  -1.263  1.00  0.00           H  
HETATM   29  H5  UNL     1       1.841   0.002  -3.009  1.00  0.00           H  
HETATM   30  H6  UNL     1      -0.085  -1.255  -2.421  1.00  0.00           H  
HETATM   31  H7  UNL     1      -0.185   1.965  -0.211  1.00  0.00           H  
HETATM   32  H8  UNL     1      -4.423  -0.207   0.830  1.00  0.00           H  
HETATM   33  H9  UNL     1      -3.524  -2.350  -0.093  1.00  0.00           H  
HETATM   34  H10 UNL     1      -2.352  -1.659   2.311  1.00  0.00           H  
HETATM   35  H11 UNL     1      -0.531  -2.156   1.261  1.00  0.00           H  
HETATM   36  H12 UNL     1       1.026  -3.199  -1.177  1.00  0.00           H  
HETATM   37  H13 UNL     1       0.933  -3.856   0.466  1.00  0.00           H  
HETATM   38  H14 UNL     1       2.493  -1.645   2.318  1.00  0.00           H  
HETATM   39  H15 UNL     1       3.451  -2.890   1.358  1.00  0.00           H  
HETATM   40  H16 UNL     1       1.787  -3.245   2.020  1.00  0.00           H  
HETATM   41  H17 UNL     1       0.905  -0.731   1.711  1.00  0.00           H  
HETATM   42  H18 UNL     1       1.719   1.311   1.021  1.00  0.00           H  
HETATM   43  H19 UNL     1       3.056   0.174   0.926  1.00  0.00           H  
HETATM   44  H20 UNL     1      -4.039   4.743   0.929  1.00  0.00           H  
HETATM   45  H21 UNL     1      -4.112   3.973  -0.751  1.00  0.00           H  
CONECT    1    2   25   26   27
CONECT    2    3
CONECT    3    4   21   28
CONECT    4    5    5   29
CONECT    5    6   30
CONECT    6    7   16   20
CONECT    7    8    8   12
CONECT    8    9   31
CONECT    9   10   10   24
CONECT   10   11   22
CONECT   11   12   12   32
CONECT   12   13
CONECT   13   14   15   33
CONECT   14   34
CONECT   15   16
CONECT   16   17   35
CONECT   17   18   36   37
CONECT   18   19   20
CONECT   19   38   39   40
CONECT   20   21   41
CONECT   21   42   43
CONECT   22   23
CONECT   23   24   44   45
END

HMDB0302721
     RDKit          3D
Pretazettine
 45 49  0  0  0  0  0  0  0  0999 V2000
    3.4532    2.6120   -1.8795 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2896    2.0990   -1.3686 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3597    0.7596   -1.0138 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5179   -0.0232   -1.9563 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4565   -0.7195   -1.6529 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0132   -0.7807   -0.2533 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1691    0.0355    0.0316 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0833    1.4100    0.0133 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1887    2.2277    0.2867 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3972    1.6334    0.5823 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4581    0.2430    0.5941 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3775   -0.5546    0.3268 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5782   -2.0384    0.3624 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.4966   -2.4151    1.7029 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5491   -2.6633   -0.3957 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4064   -2.2190    0.1388 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8583   -2.9043   -0.1301 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8529   -1.9732    0.3687 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4640   -2.4763    1.5900 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1678   -0.6985    0.6430 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0869    0.4648    0.4134 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3101    2.6550    0.8091 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7836    3.8776    0.3186 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3747    3.6005    0.3354 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3076    2.5479   -1.1647 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6956    2.1729   -2.8720 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2933    3.6953   -2.0553 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4220    0.4566   -1.2633 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8408    0.0018   -3.0094 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0847   -1.2546   -2.4210 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1852    1.9645   -0.2115 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4230   -0.2069    0.8301 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5237   -2.3497   -0.0927 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3520   -1.6585    2.3106 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5312   -2.1560    1.2610 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0260   -3.1988   -1.1773 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9334   -3.8565    0.4656 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4931   -1.6455    2.3179 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4511   -2.8902    1.3581 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7867   -3.2448    2.0204 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9052   -0.7306    1.7112 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7189    1.3115    1.0212 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0565    0.1743    0.9264 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0391    4.7426    0.9285 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1119    3.9726   -0.7506 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  6  5  1  6
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
 10 22  1  0
 22 23  1  0
 23 24  1  0
 21  3  1  0
 16  6  1  0
 20  6  1  0
 12  7  1  0
 24  9  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  3 28  1  6
  4 29  1  0
  5 30  1  0
  8 31  1  0
 11 32  1  0
 13 33  1  6
 14 34  1  0
 16 35  1  1
 17 36  1  0
 17 37  1  0
 19 38  1  0
 19 39  1  0
 19 40  1  0
 20 41  1  1
 21 42  1  0
 21 43  1  0
 23 44  1  0
 23 45  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₁₈H₂₁NO₅

Average Molecular Weight

331.363

Monoisotopic Molecular Weight

331.141972787

IUPAC Name

(1S,11R,13R,16S,18S)-18-methoxy-15-methyl-5,7,12-trioxa-15-azapentacyclo[11.7.0.0¹,¹⁶.0²,¹⁰.0⁴,⁸]icosa-2,4(8),9,19-tetraen-11-ol

Traditional Name

pretazettine

CAS Registry Number

Not Available

SMILES

CO[C@H]1C[C@@H]2N(C)C[C@@H]3O[C@@H](O)C4=CC5=C(OCO5)C=C4[C@@]23C=C1

InChI Identifier

InChI=1S/C18H21NO5/c1-19-8-16-18(4-3-10(21-2)5-15(18)19)12-7-14-13(22-9-23-14)6-11(12)17(20)24-16/h3-4,6-7,10,15-17,20H,5,8-9H2,1-2H3/t10-,15+,16+,17-,18+/m1/s1

InChI Key

KLJOYDMUWKSYBP-YNBLHMCPSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as tazettine-type amaryllidaceae alkaloids. These are amaryllidaceae alkaloids derived from the haemanthamine-type alkaloids, which are characterized as a linkage between C6 and C11 by an oxygen atom to form a [3,4-g]benzopyran framework.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Amaryllidaceae alkaloids

Sub Class

Tazettine-type amaryllidaceae alkaloids

Direct Parent

Tazettine-type amaryllidaceae alkaloids

Alternative Parents

Substituents

Tazettine alkaloid skeleton
Benzopyran
Isochromane
2-benzopyran
Benzodioxole
Indole or derivatives
Aralkylamine
N-alkylpyrrolidine
Benzenoid
Pyrrolidine
Hemiacetal
Tertiary amine
Tertiary aliphatic amine
Oxacycle
Acetal
Ether
Dialkyl ether
Azacycle
Organoheterocyclic compound
Amine
Organooxygen compound
Organonitrogen compound
Hydrocarbon derivative
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

alkaloid (CHEBI:8402 )

Ontology

Not Available

Lovage (FooDB: FOOD00100)

Process

Not Available

Role

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	0.73	ALOGPS
logP	1.1	ChemAxon
logS	-2.1	ALOGPS
pKa (Strongest Acidic)	11.54	ChemAxon
pKa (Strongest Basic)	7.71	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	60.39 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	86.89 m³·mol⁻¹	ChemAxon
Polarizability	34.52 Å³	ChemAxon
Number of Rings	5	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]+	179.274	32859911
AllCCS	[M+H-H2O]+	176.118	32859911
AllCCS	[M+Na]+	183.034	32859911
AllCCS	[M+NH4]+	182.195	32859911
AllCCS	[M-H]-	182.47	32859911
AllCCS	[M+Na-2H]-	182.118	32859911
AllCCS	[M+HCOO]-	181.87	32859911
DeepCCS	[M-2H]-	216.786	30932474
DeepCCS	[M+Na]+	192.211	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 - Pretazettine 10V, Positive-QTOF	splash10-001i-0009000000-e2435e272ca9f1a2d42f	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pretazettine 20V, Positive-QTOF	splash10-0f89-0059000000-cafe65902dcbae1ebf7d	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pretazettine 40V, Positive-QTOF	splash10-054o-1490000000-3350b494f2ef37f52c8c	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pretazettine 10V, Negative-QTOF	splash10-001i-0119000000-8e3643f4ca920a1640fe	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pretazettine 20V, Negative-QTOF	splash10-001i-0059000000-11edba5eac58052a23ab	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pretazettine 40V, Negative-QTOF	splash10-03ds-2931000000-9cde7fc633100e58bb8c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pretazettine 10V, Positive-QTOF	splash10-001i-0009000000-918c8ddc5fbef0f4ca7c	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pretazettine 20V, Positive-QTOF	splash10-001i-0009000000-fefcf3e894e6993c6dbc	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pretazettine 40V, Positive-QTOF	splash10-0f80-0592000000-fc3653dcf02c25c99288	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pretazettine 10V, Negative-QTOF	splash10-001i-0009000000-84445a1cf82498088abb	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pretazettine 20V, Negative-QTOF	splash10-001i-0009000000-51577d2cac66b76a3ea0	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pretazettine 40V, Negative-QTOF	splash10-0inj-0389000000-76f32be696d3d3ea0c2f	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

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

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 Pretazettine (HMDB0302721)

MOL for HMDB0302721 (Pretazettine)

3D MOL for HMDB0302721 (Pretazettine)

3D SDF for HMDB0302721 (Pretazettine)

3D-SDF for HMDB0302721 (Pretazettine)

PDB for HMDB0302721 (Pretazettine)

3D PDB for HMDB0302721 (Pretazettine)

SMILES for HMDB0302721 (Pretazettine)

INCHI for HMDB0302721 (Pretazettine)

Structure for HMDB0302721 (Pretazettine)

3D Structure for HMDB0302721 (Pretazettine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

MS/MS Spectra