NP-MRD: Showing NP-Card for (+)-Tazettine (NP0066799)

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Record Information

Version

2.0

Created at

2022-04-28 11:01:46 UTC

Updated at

2022-04-28 11:01:46 UTC

NP-MRD ID

NP0066799

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(+)-Tazettine

Description

Tazettine, also known as sekisanolin or ungernine, 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. (+)-Tazettine is found in Brunsvigia gregaria, Crinum amabile , Crinum asiaticum var.sinicum , Crinum jagus, Crinum moorei, Cyrtanthus falcatus, Cyrtanthus obliquus , Galanthus caucasicus , Galanthus elwesii, Galanthus nivalis , Haemanthus albiflos, Hippeastrum equestre, Hippeastrum morelianum, Hippeastrum puniceum, Hippeastrum vittatum L.'Herr., Hymenocallis arenicola Northrop H, Hymenocallis cayamansis, Hymenocallis littoralis , Hymenocallis rotata, Hymenocallis x festalis, Lapiedra martinezii, Leucojum aestivum L. , Leucojum vernum, Lycoris aurea , Lycoris radiata , Lycoris sanguinea, Lycoris sanguinea Maxim, Lycoris squamigera, Narcissus asturiensis, Narcissus bujei, Narcissus cantabricus, Narcissus cyclamineus, Narcissus folli, Narcissus jonquilla, Narcissus papyraceus Kerl-Gawl, Narcissus poeticus L., Narcissus pseudonarcissus, Narcissus tarzettus, Narcissus tazetta L. , Pancratium biflorum Roxb., Pancratium canariense, Pancratium maritimum, Pancratium trianthum, Sprekelia formosissima, Sternbergia lutea, Sternbergia lutea ker-Gawl, Ungernia sewerzowii, Ungernia spiralis, Ungernia trisphaera, Ungernia vvedenskyi, Zephyranthes candida and Zephyranthes sulphurea. (+)-Tazettine was first documented in 2021 (PMID: 33434626). Based on a literature review a small amount of articles have been published on tazettine (PMID: 35483192) (PMID: 35448871) (PMID: 33578992) (PMID: 33401696).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 45 49  0  0  0  0  0  0  0  0999 V2000
   -4.6774    2.0011    0.6544 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3821    2.2434    0.2156 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5246    1.1677    0.4522 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4786    1.5540    1.4352 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3229    0.9161    1.3638 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0296   -0.1319    0.4141 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4821    0.0385    0.0712 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8971    1.1544   -0.6205 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2260    1.3645   -0.9645 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1636    0.4402   -0.6104 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7525   -0.6795    0.0827 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4315   -0.8969    0.4294 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0677   -2.1350    1.1805 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8878   -1.8924    1.8316 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1551   -1.4933    1.0531 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.2971   -1.4257    1.8586 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4790   -2.4334   -0.0859 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2205   -1.5993   -0.9737 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5489   -1.9184   -1.2097 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8425   -0.2420   -0.7921 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.9558    0.7466   -0.8643 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3999    0.8800   -1.0663 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2691    2.1270   -1.7107 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8834    2.3814   -1.6425 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1363    1.1232    0.1557 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6425    1.8982    1.7530 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2953    2.8740    0.3763 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1438    0.3927    0.9431 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7145    2.3264    2.1480 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4322    1.2159    2.0961 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2096    1.9395   -0.9398 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4823   -1.4232    0.3717 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8386   -2.3481    1.9789 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0697   -3.0344    0.5385 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0891   -1.7756    1.4206 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3943   -2.8235   -0.6049 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0915   -3.2669    0.3258 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7006   -3.0124   -1.0936 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3241   -1.4295   -0.6072 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8011   -1.7106   -2.2907 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1687   -0.0205   -1.6684 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6352    1.6796   -1.3889 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7774    0.3288   -1.4814 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6269    1.9841   -2.7534 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8605    2.9153   -1.2267 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3 21  1  0
 21 20  1  0
 20 18  1  0
 18 19  1  0
 18 17  1  0
 17 15  1  0
 15 16  1  1
 15 14  1  0
 14 13  1  0
 13 12  1  0
 12 11  2  0
 11 10  1  0
 10  9  2  0
  9 24  1  0
 24 23  1  0
 23 22  1  0
  9  8  1  0
  8  7  2  0
  7  6  1  0
  6  5  1  1
  5  4  2  0
  4  3  1  0
  6 20  1  0
  6 15  1  0
  7 12  1  0
 22 10  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  3 28  1  1
 21 42  1  0
 21 43  1  0
 20 41  1  6
 19 38  1  0
 19 39  1  0
 19 40  1  0
 17 36  1  0
 17 37  1  0
 16 35  1  0
 13 33  1  0
 13 34  1  0
 11 32  1  0
 23 44  1  0
 23 45  1  0
  8 31  1  0
  5 30  1  0
  4 29  1  0
M  END


  Mrv1652304282213012D          

 24 28  0  0  1  0            999 V2000
    3.4305    0.6255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6899   -0.1576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1414   -0.7738    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3335   -0.6069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1165    0.0675    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6226    0.7925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2661    0.3431    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7176   -0.2731    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9770   -1.0563    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7849   -1.2232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0380    0.0581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0436    0.8791    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.8495    1.0552    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2579    1.7721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0829    1.7768    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4995    1.0647    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0911    0.3478    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4913    2.4936    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3163    2.4983    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5727    1.4276    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1077   -0.8286    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5149   -0.1529    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7654    0.6332    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0952    1.1143    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  1  6  1  0  0  0  0
  7  5  1  6  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  4 10  1  0  0  0  0
  8 11  1  0  0  0  0
 11 12  1  0  0  0  0
 13 12  1  1  0  0  0
  7 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
  7 17  1  0  0  0  0
 15 18  1  6  0  0  0
 18 19  1  0  0  0  0
 12 20  1  0  0  0  0
  8 21  1  1  0  0  0
  2 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
  1 24  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0066799

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CO[C@H]1C[C@@H]2N(C)C[C@@]3(O)OCC4=CC5=C(OCO5)C=C4[C@@]23C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C18H21NO5/c1-19-9-18(20)17(4-3-12(21-2)6-16(17)19)13-7-15-14(22-10-23-15)5-11(13)8-24-18/h3-5,7,12,16,20H,6,8-10H2,1-2H3/t12-,16+,17+,18-/m1/s1

> <INCHI_KEY>
YLWAQARRNQVEHD-PBZHRCKQSA-N

> <FORMULA>
C18H21NO5

> <MOLECULAR_WEIGHT>
331.368

> <EXACT_MASS>
331.14197278

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
45

> <JCHEM_AVERAGE_POLARIZABILITY>
34.363350910240406

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,13S,16S,18S)-18-methoxy-15-methyl-5,7,12-trioxa-15-azapentacyclo[11.7.0.0^{1,16}.0^{2,10}.0^{4,8}]icosa-2,4(8),9,19-tetraen-13-ol

> <ALOGPS_LOGP>
0.48

> <JCHEM_LOGP>
1.2791916213333336

> <ALOGPS_LOGS>
-2.17

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.086838077509851

> <JCHEM_PKA_STRONGEST_BASIC>
7.557602653536731

> <JCHEM_POLAR_SURFACE_AREA>
60.390000000000015

> <JCHEM_REFRACTIVITY>
87.32260000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.24e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,13S,16S,18S)-18-methoxy-15-methyl-5,7,12-trioxa-15-azapentacyclo[11.7.0.0^{1,16}.0^{2,10}.0^{4,8}]icosa-2,4(8),9,19-tetraen-13-ol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0       6.404   1.168   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.888  -0.294   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.864  -1.445   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.356  -1.133   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.951   0.126   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.895   1.479   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.363   0.641   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.339  -0.510   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       1.824  -1.972   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       3.332  -2.283   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.071   0.109   0.000  0.00  0.00           C+0
HETATM   12  N   UNK     0       0.081   1.641   0.000  0.00  0.00           N+0
HETATM   13  C   UNK     0       1.586   1.970   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.348   3.308   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.888   3.317   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.666   1.987   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.903   0.649   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       4.650   4.655   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       6.190   4.663   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -1.069   2.665   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       0.201  -1.547   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       8.428  -0.285   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       8.895   1.182   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       7.644   2.080   0.000  0.00  0.00           O+0
CONECT    1    2    6   24                                                  
CONECT    2    1    3   22                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   10                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5    1                                                       
CONECT    7    5    8   13   17                                             
CONECT    8    7    9   11   21                                             
CONECT    9    8   10                                                       
CONECT   10    9    4                                                       
CONECT   11    8   12                                                       
CONECT   12   11   13   20                                                  
CONECT   13   12    7   14                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   18                                                  
CONECT   16   15   17                                                       
CONECT   17   16    7                                                       
CONECT   18   15   19                                                       
CONECT   19   18                                                            
CONECT   20   12                                                            
CONECT   21    8                                                            
CONECT   22    2   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23    1                                                       
MASTER        0    0    0    0    0    0    0    0   24    0   56    0
END

View in JSmol

Synonyms

Value	Source
Sekisanin	ChEBI
Sekisanolin	ChEBI
Sekisanoline	ChEBI
Ungernine	ChEBI

Chemical Formula

C₁₈H₂₁NO₅

Average Mass

331.3680 Da

Monoisotopic Mass

331.14197 Da

IUPAC Name

(1S,13S,16S,18S)-18-methoxy-15-methyl-5,7,12-trioxa-15-azapentacyclo[11.7.0.0^{1,16}.0^{2,10}.0^{4,8}]icosa-2,4(8),9,19-tetraen-13-ol

Traditional Name

(1S,13S,16S,18S)-18-methoxy-15-methyl-5,7,12-trioxa-15-azapentacyclo[11.7.0.0^{1,16}.0^{2,10}.0^{4,8}]icosa-2,4(8),9,19-tetraen-13-ol

CAS Registry Number

Not Available

SMILES

CO[C@H]1C[C@@H]2N(C)C[C@@]3(O)OCC4=CC5=C(OCO5)C=C4[C@@]23C=C1

InChI Identifier

InChI=1S/C18H21NO5/c1-19-9-18(20)17(4-3-12(21-2)6-16(17)19)13-7-15-14(22-10-23-15)5-11(13)8-24-18/h3-5,7,12,16,20H,6,8-10H2,1-2H3/t12-,16+,17+,18-/m1/s1

InChI Key

YLWAQARRNQVEHD-PBZHRCKQSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Brunsvigia gregaria	Plant	KNApSAcK
Crinum amabile	Plant	KNApSAcK
Crinum asiaticum var.sinicum	Plant	KNApSAcK
Crinum jagus	LOTUS Database	35616633
Crinum moorei	LOTUS Database	35616633
Cyrtanthus falcatus	LOTUS Database	35616633
Cyrtanthus obliquus	Plant	KNApSAcK
Galanthus caucasicus	Plant	KNApSAcK
Galanthus elwesii	Plant	KNApSAcK
Galanthus nivalis	Plant	KNApSAcK
Haemanthus albiflos	LOTUS Database	35616633
Hippeastrum equestre	Plant	KNApSAcK
Hippeastrum morelianum	LOTUS Database	35616633
Hippeastrum puniceum	LOTUS Database	35616633
Hippeastrum vittatum L.'Herr.	Plant	KNApSAcK
Hymenocallis arenicola Northrop H	Plant	KNApSAcK
Hymenocallis cayamansis	Plant	KNApSAcK
Hymenocallis littoralis	Plant	KNApSAcK
Hymenocallis rotata	LOTUS Database	35616633
Hymenocallis x festalis	Plant	KNApSAcK
Lapiedra martinezii	LOTUS Database	35616633
Leucojum aestivum	Plant	KNApSAcK
Leucojum vernum	Plant	KNApSAcK
Lycoris aurea	Plant	KNApSAcK
Lycoris radiata	Plant	KNApSAcK
Lycoris sanguinea	LOTUS Database	35616633
Lycoris sanguinea Maxim	Plant	KNApSAcK
Lycoris squamigera	LOTUS Database	35616633
Narcissus asturiensis	Plant	KNApSAcK
Narcissus bujei	Plant	KNApSAcK
Narcissus cantabricus	LOTUS Database	35616633
Narcissus cyclamineus	Plant	KNApSAcK
Narcissus folli	Plant	KNApSAcK
Narcissus jonquilla	Plant	KNApSAcK
Narcissus papyraceus Kerl-Gawl	Plant	KNApSAcK
Narcissus poeticus	Plant	KNApSAcK
Narcissus pseudonarcissus	Plant	KNApSAcK
Narcissus tarzettus	Plant	KNApSAcK
Narcissus tazetta	Plant	KNApSAcK
Pancratium biflorum Roxb.	Plant	KNApSAcK
Pancratium canariense	Plant	KNApSAcK
Pancratium maritimum	Plant	KNApSAcK
Pancratium trianthum	Plant	KNApSAcK
Sprekelia formosissima	Plant	KNApSAcK
Sternbergia lutea	LOTUS Database	35616633
Sternbergia lutea ker-Gawl	Plant	KNApSAcK
Ungernia sewerzowii	Plant	KNApSAcK
Ungernia spiralis	Plant	KNApSAcK
Ungernia trisphaera	Plant	KNApSAcK
Ungernia vvedenskyi	Plant	KNApSAcK
Zephyranthes candida	Plant	KNApSAcK
Zephyranthes sulphurea	Plant	KNApSAcK

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

indole alkaloid (CHEBI:32185 )
indole alkaloid fundamental parent (CHEBI:32185 )

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	0.48	ALOGPS
logP	1.28	ChemAxon
logS	-2.2	ALOGPS
pKa (Strongest Acidic)	11.09	ChemAxon
pKa (Strongest Basic)	7.56	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	87.32 m³·mol⁻¹	ChemAxon
Polarizability	34.36 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

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00024438

Chemspider ID

4479445

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5321780

PDB ID

Not Available

ChEBI ID

32185

Good Scents ID

Not Available

References

General References

Aleya F, Xianmin C, Anthony H, Meriel J: Relative expression of putative genes involved in galanthamine and other Amaryllidaceae alkaloids biosynthesis in Narcissus field and in vitro tissues. Gene. 2021 Mar 30;774:145424. doi: 10.1016/j.gene.2021.145424. Epub 2021 Jan 9. [PubMed:33434626 ]
Sierra K, de Andrade JP, R Tallini L, Osorio EH, Yanez O, Osorio MI, Oleas NH, Garcia-Beltran O, de S Borges W, Bastida J, Osorio E, Cortes N: In vitro and in silico analysis of galanthine from Zephyranthes carinata as an inhibitor of acetylcholinesterase. Biomed Pharmacother. 2022 Jun;150:113016. doi: 10.1016/j.biopha.2022.113016. Epub 2022 Apr 25. [PubMed:35483192 ]
Masi M, Di Lecce R, Merindol N, Girard MP, Berthoux L, Desgagne-Penix I, Calabro V, Evidente A: Cytotoxicity and Antiviral Properties of Alkaloids Isolated from Pancratium maritimum. Toxins (Basel). 2022 Apr 7;14(4). pii: toxins14040262. doi: 10.3390/toxins14040262. [PubMed:35448871 ]
Spina R, Saliba S, Dupire F, Ptak A, Hehn A, Piutti S, Poinsignon S, Leclerc S, Bouguet-Bonnet S, Laurain-Mattar D: Molecular Identification of Endophytic Bacteria in Leucojum aestivum In Vitro Culture, NMR-Based Metabolomics Study and LC-MS Analysis Leading to Potential Amaryllidaceae Alkaloid Production. Int J Mol Sci. 2021 Feb 10;22(4). pii: ijms22041773. doi: 10.3390/ijms22041773. [PubMed:33578992 ]
Zaragoza-Puchol D, Ortiz JE, Orden AA, Sanchez M, Palermo J, Tapia A, Bastida J, Feresin GE: Alkaloids Analysis of Habranthus cardenasianus (Amaryllidaceae), Anti-Cholinesterase Activity and Biomass Production by Propagation Strategies. Molecules. 2021 Jan 2;26(1). pii: molecules26010192. doi: 10.3390/molecules26010192. [PubMed:33401696 ]

Showing NP-Card for (+)-Tazettine (NP0066799)

MOL for NP0066799 ((+)-Tazettine)

3D MOL for NP0066799 ((+)-Tazettine)

3D SDF for NP0066799 ((+)-Tazettine)

3D-SDF for NP0066799 ((+)-Tazettine)

PDB for NP0066799 ((+)-Tazettine)

3D PDB for NP0066799 ((+)-Tazettine)

SMILES for NP0066799 ((+)-Tazettine)

INCHI for NP0066799 ((+)-Tazettine)

Structure for NP0066799 ((+)-Tazettine)

3D Structure for NP0066799 ((+)-Tazettine)