NP-MRD: Showing NP-Card for (+)-11-Hydroxyvittatine (NP0069371)

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Record Information

Version

2.0

Created at

2022-04-28 14:43:25 UTC

Updated at

2022-04-28 14:43:25 UTC

NP-MRD ID

NP0069371

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(+)-11-Hydroxyvittatine

Description

11-Hydroxyvittatine belongs to the class of organic compounds known as crinine- and haemanthamine-type amaryllidaceae alkaloids. These are amaryllidaceae alkaloids compounds with a structure based on the crinine or haemanthamine backbone. Both backbones have a common 5,10b-ethano bridge moiety in their frameworks, which is a very significant taxonomic feature, and the configurations of the 5,10b-ethano bridge are opposite to each other. (+)-11-Hydroxyvittatine is found in Amaryllis belladonna, Galanthus elewesii, Galanthus elwesii, Galanthus plicatus, Hippeastrum papilio, Hippeastrum puniceum, Pancratium canariense, Pancratium maritimum, Pancratium sickenbergeri and Sternbergia lutea. (+)-11-Hydroxyvittatine was first documented in 2003 (PMID: 14598220). Based on a literature review a significant number of articles have been published on 11-Hydroxyvittatine (PMID: 22260001) (PMID: 35448871) (PMID: 30963375) (PMID: 16309304) (PMID: 15587597) (PMID: 30657047).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 38 42  0  0  0  0  0  0  0  0999 V2000
   -4.4336    1.6189   -1.2944 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3569    1.2853   -0.4295 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.2485    2.1928   -0.7088 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9892    1.8446   -0.4869 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6704    0.5304    0.0477 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7226    0.0962   -0.1480 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7809    0.9803   -0.1524 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0908    0.5695   -0.3343 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3691   -0.7691   -0.5197 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3308   -1.6679   -0.5191 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0114   -1.2364   -0.3338 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0759   -2.2548   -0.3445 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2578   -1.6584    0.2398 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0108   -1.2083    1.5696 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9809    0.3251    1.5116 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1097    0.7989    2.2745 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5785   -0.5106   -0.5845 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.0117   -0.1528   -0.5252 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7601   -0.8908   -0.6759 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3647    0.2850   -0.1467 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3165    1.2230   -0.3828 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2351    1.1485   -0.9902 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7661    1.5622    0.5893 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4786    3.2059   -1.1204 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2340    2.5856   -0.7246 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5876    2.0198   -0.0104 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5557   -2.7089   -0.6641 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2463   -2.5780   -1.3915 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2035   -3.1492    0.2494 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7928   -1.5717    2.2443 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0170   -1.5341    1.8983 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9267    0.7288    1.8526 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6024    0.0174    2.6280 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2308   -0.7057   -1.6388 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5780   -0.6873    0.2712 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4781   -0.5371   -1.4844 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4980    0.2260    0.9393 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2598    0.5768   -0.7048 H   0  0  0  0  0  0  0  0  0  0  0  0
 16 15  1  0
 15 14  1  0
 14 13  1  0
 13 12  1  0
 12 11  1  0
 11 10  2  0
 10  9  1  0
  9  8  2  0
  8 21  1  0
 21 20  1  0
 20 19  1  0
  8  7  1  0
  7  6  2  0
  6  5  1  0
  5  4  1  6
  4  3  2  0
  3  2  1  0
  2  1  1  0
  2 18  1  0
 18 17  1  0
  5 15  1  0
 17  5  1  0
 17 13  1  0
  6 11  1  0
 19  9  1  0
 16 33  1  0
 15 32  1  1
 14 30  1  0
 14 31  1  0
 12 28  1  0
 12 29  1  0
 10 27  1  0
 20 37  1  0
 20 38  1  0
  7 26  1  0
  4 25  1  0
  3 24  1  0
  2 23  1  1
  1 22  1  0
 18 35  1  0
 18 36  1  0
 17 34  1  6
M  END


  Mrv1652304282216432D          

 21 25  0  0  1  0            999 V2000
    1.2158   -0.6165    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5015   -1.0291    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3787   -1.8450    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9400   -2.4496    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7627   -2.3877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2272   -1.7060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0316   -1.8893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5926   -1.2844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3492   -0.4961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5449   -0.3128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9839   -0.9177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0237   -0.0211    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6840   -0.5158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4175   -1.2966    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8989   -1.3781    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0808   -1.4845    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4204   -0.8292    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1034   -0.0675    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7147    0.0389    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2385   -0.9355    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1803   -0.5646    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
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
  1 11  1  1  0  0  0
  6 11  1  0  0  0  0
  9 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
  8 14  1  0  0  0  0
 15  4  1  1  0  0  0
  1 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
  1 19  1  0  0  0  0
 17 20  1  6  0  0  0
  2 21  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0069371

> <DATABASE_NAME>
NP-MRD

> <SMILES>
O[C@@H]1CN2CC3=CC4=C(OCO4)C=C3[C@]11C=C[C@@H](O)C[C@H]21

> <INCHI_IDENTIFIER>
InChI=1S/C16H17NO4/c18-10-1-2-16-11-5-13-12(20-8-21-13)3-9(11)6-17(7-15(16)19)14(16)4-10/h1-3,5,10,14-15,18-19H,4,6-8H2/t10-,14+,15-,16+/m1/s1

> <INCHI_KEY>
KWAOMPWGIIXDPH-NWLYGAKOSA-N

> <FORMULA>
C16H17NO4

> <MOLECULAR_WEIGHT>
287.315

> <EXACT_MASS>
287.115758031

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
38

> <JCHEM_AVERAGE_POLARIZABILITY>
29.565469694161685

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,13S,15S,18S)-5,7-dioxa-12-azapentacyclo[10.5.2.0^{1,13}.0^{2,10}.0^{4,8}]nonadeca-2,4(8),9,16-tetraene-15,18-diol

> <ALOGPS_LOGP>
0.66

> <JCHEM_LOGP>
0.1826226556666668

> <ALOGPS_LOGS>
-1.68

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
14.921831969492807

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.049491816751907

> <JCHEM_PKA_STRONGEST_BASIC>
8.128018362533648

> <JCHEM_POLAR_SURFACE_AREA>
62.16000000000001

> <JCHEM_REFRACTIVITY>
76.35289999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.05e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,13S,15S,18S)-5,7-dioxa-12-azapentacyclo[10.5.2.0^{1,13}.0^{2,10}.0^{4,8}]nonadeca-2,4(8),9,16-tetraene-15,18-diol

> <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       2.270  -1.151   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.936  -1.921   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.707  -3.444   0.000  0.00  0.00           C+0
HETATM    4  N   UNK     0       1.755  -4.573   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0       3.290  -4.457   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.158  -3.184   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.659  -3.527   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.706  -2.398   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.252  -0.926   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.750  -0.584   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.703  -1.713   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       7.511  -0.039   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       8.743  -0.963   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       8.246  -2.420   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       1.678  -2.573   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.151  -2.771   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -0.785  -1.548   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -0.193  -0.126   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.334   0.073   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      -2.312  -1.746   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      -0.337  -1.054   0.000  0.00  0.00           O+0
CONECT    1    2   11   15   19                                             
CONECT    2    1    3   21                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   15                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7   11                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   14                                                  
CONECT    9    8   10   12                                                  
CONECT   10    9   11                                                       
CONECT   11   10    1    6                                                  
CONECT   12    9   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13    8                                                       
CONECT   15    4    1   16                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   20                                                  
CONECT   18   17   19                                                       
CONECT   19   18    1                                                       
CONECT   20   17                                                            
CONECT   21    2                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   50    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₆H₁₇NO₄

Average Mass

287.3150 Da

Monoisotopic Mass

287.11576 Da

IUPAC Name

(1S,13S,15S,18S)-5,7-dioxa-12-azapentacyclo[10.5.2.0^{1,13}.0^{2,10}.0^{4,8}]nonadeca-2,4(8),9,16-tetraene-15,18-diol

Traditional Name

(1S,13S,15S,18S)-5,7-dioxa-12-azapentacyclo[10.5.2.0^{1,13}.0^{2,10}.0^{4,8}]nonadeca-2,4(8),9,16-tetraene-15,18-diol

CAS Registry Number

Not Available

SMILES

O[C@@H]1CN2CC3=CC4=C(OCO4)C=C3[C@]11C=C[C@@H](O)C[C@H]21

InChI Identifier

InChI=1S/C16H17NO4/c18-10-1-2-16-11-5-13-12(20-8-21-13)3-9(11)6-17(7-15(16)19)14(16)4-10/h1-3,5,10,14-15,18-19H,4,6-8H2/t10-,14+,15-,16+/m1/s1

InChI Key

KWAOMPWGIIXDPH-NWLYGAKOSA-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
Amaryllis belladonna	Plant	KNApSAcK
Galanthus elewesii	Plant	KNApSAcK
Galanthus elwesii	LOTUS Database	35616633
Galanthus plicatus	LOTUS Database	35616633
Hippeastrum papilio	LOTUS Database	35616633
Hippeastrum puniceum	LOTUS Database	35616633
Pancratium canariense	LOTUS Database	35616633
Pancratium maritimum	LOTUS Database	35616633
Pancratium sickenbergeri	LOTUS Database	35616633
Sternbergia lutea	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as crinine- and haemanthamine-type amaryllidaceae alkaloids. These are amaryllidaceae alkaloids compounds with a structure based on the crinine or haemanthamine backbone. Both backbones have a common 5,10b-ethano bridge moiety in their frameworks, which is a very significant taxonomic feature, and the configurations of the 5,10b-ethano bridge are opposite to each other.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Amaryllidaceae alkaloids

Sub Class

Crinine- and Haemanthamine-type amaryllidaceae alkaloids

Direct Parent

Crinine- and Haemanthamine-type amaryllidaceae alkaloids

Alternative Parents

Substituents

Hemanthamine/crinine alkaloid skeleton
Benzoquinoline
Phenanthridine
Benzazepine
Quinoline
Tetrahydroisoquinoline
Benzodioxole
Indole or derivatives
Azepine
Aralkylamine
N-alkylpyrrolidine
Benzenoid
Pyrrolidine
Tertiary aliphatic amine
1,2-aminoalcohol
Secondary alcohol
Tertiary amine
Oxacycle
Organoheterocyclic compound
Acetal
Azacycle
Organooxygen compound
Organonitrogen compound
Hydrocarbon derivative
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Alcohol
Amine
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

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	0.66	ALOGPS
logP	0.18	ChemAxon
logS	-1.7	ALOGPS
pKa (Strongest Acidic)	14.05	ChemAxon
pKa (Strongest Basic)	8.13	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	62.16 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	76.35 m³·mol⁻¹	ChemAxon
Polarizability	29.57 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

C00027615

Chemspider ID

28512985

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

70682698

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Zhao YY, Liang YQ, Chen Y, Sun H, Wang M, Feng X: [Study on chemical constituents of the bulbs of Lycoris longituba]. Zhong Yao Cai. 2011 Sep;34(9):1366-8. [PubMed:22260001 ]
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 ]
Endo Y, Sugiura Y, Funasaki M, Kagechika H, Ishibashi M, Ohsaki A: Two new alkaloids from Crinum asiaticum var. japonicum. J Nat Med. 2019 Jun;73(3):648-652. doi: 10.1007/s11418-019-01304-9. Epub 2019 Apr 8. [PubMed:30963375 ]
Forgo P, Hohmann J: Leucovernine and acetylleucovernine, alkaloids from Leucojum vernum. J Nat Prod. 2005 Nov;68(11):1588-91. doi: 10.1021/np050126f. [PubMed:16309304 ]
Aboul-Ela MA, El-Lakany AM, Hammoda HM: Alkaloids from the bulbs of Crinum bulbispermum. Pharmazie. 2004 Nov;59(11):894-6. [PubMed:15587597 ]
Cole ER, de Andrade JP, Filho JFA, Schmitt EFP, Alves-Araujo A, Bastida J, Endringer DC, de S Borges W, Lacerda V: Cytotoxic and Genotoxic Activities of Alkaloids from the Bulbs of Griffinia gardneriana and Habranthus itaobinus (Amaryllidaceae). Anticancer Agents Med Chem. 2019;19(5):707-717. doi: 10.2174/1871520619666190118122523. [PubMed:30657047 ]
Cedron JC, Gutierrez D, Flores N, Ravelo AG, Estevez-Braun A: Synthesis and antimalarial activity of new haemanthamine-type derivatives. Bioorg Med Chem. 2012 Sep 15;20(18):5464-72. doi: 10.1016/j.bmc.2012.07.036. Epub 2012 Jul 31. [PubMed:22910226 ]
Abou-Donia AH, Toaima SM, Hammoda HM, Shawky E, Kinoshita E, Takayama H: Phytochemical and biological investigation of Hymenocallis littoralis SALISB. Chem Biodivers. 2008 Feb;5(2):332-40. doi: 10.1002/cbdv.200890031. [PubMed:18293433 ]
Evidente A, Andolfi A, Abou-Donia AH, Touema SM, Hammoda HM, Shawky E, Motta A: (-)-Amarbellisine, a lycorine-type alkaloid from Amaryllis belladonna L. growing in Egypt. Phytochemistry. 2004 Jul;65(14):2113-8. doi: 10.1016/j.phytochem.2004.03.020. [PubMed:15279981 ]
Unver N, Kaya GI, Werner C, Verpoorte R, Gozler B: Galanthindole: a new indole alkaloid from Galanthus plicatus ssp. byzantinus. Planta Med. 2003 Sep;69(9):869-71. doi: 10.1055/s-2003-43206. [PubMed:14598220 ]

Showing NP-Card for (+)-11-Hydroxyvittatine (NP0069371)

MOL for NP0069371 ((+)-11-Hydroxyvittatine)

3D MOL for NP0069371 ((+)-11-Hydroxyvittatine)

3D SDF for NP0069371 ((+)-11-Hydroxyvittatine)

3D-SDF for NP0069371 ((+)-11-Hydroxyvittatine)

PDB for NP0069371 ((+)-11-Hydroxyvittatine)

3D PDB for NP0069371 ((+)-11-Hydroxyvittatine)

SMILES for NP0069371 ((+)-11-Hydroxyvittatine)

INCHI for NP0069371 ((+)-11-Hydroxyvittatine)

Structure for NP0069371 ((+)-11-Hydroxyvittatine)

3D Structure for NP0069371 ((+)-11-Hydroxyvittatine)