NP-MRD: Showing NP-Card for Pretazettine (NP0046792)

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Record Information

Version

2.0

Created at

2022-03-17 20:29:37 UTC

Updated at

2022-03-17 20:29:38 UTC

NP-MRD ID

NP0046792

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Pretazettine

Description

Pretazettine is found in Cyrtanthus obliquus, Hippeastrum equestre, Hippeastrum morelianum, Hymenocallis cayamansis, Hymenocallis rotata, Hymenocallis tubiflora , Ismene calithina, Leucojum aestivum , Lycoris radiata , Narcissus bicolor, Narcissus confusus, Narcissus obesus, Narcissus pallidiflorus, Narcissus papyraceus, Narcissus tazetta , Pancratium biflorum, Sprekelia formosissima, Sternbergia lutea, Zephyranthes candida and Zephyranthes carinata .

Structure

MOL SDF PDB SMILES InChI


  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>
NP0046792

> <DATABASE_NAME>
NP-MRD

> <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

$$$$

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

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₈H₂₁NO₅

Average Mass

331.3630 Da

Monoisotopic Mass

331.14197 Da

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

17322-84-8

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

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Cyrtanthus obliquus	LOTUS Database	35616633
Hippeastrum equestre	Plant	KNApSAcK
Hippeastrum morelianum	LOTUS Database	35616633
Hymenocallis cayamansis	Plant	KNApSAcK
Hymenocallis rotata	LOTUS Database	35616633
Hymenocallis tubiflora	Plant	KNApSAcK
Ismene calithina	Plant	KNApSAcK
Leucojum aestivum	Plant	KNApSAcK
Levisticum officinale	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Lycoris radiata	Plant	KNApSAcK
Narcissus bicolor	LOTUS Database	35616633
Narcissus confusus	LOTUS Database	35616633
Narcissus obesus	LOTUS Database	35616633
Narcissus pallidiflorus	LOTUS Database	35616633
Narcissus papyraceus	LOTUS Database	35616633
Narcissus tazetta	Plant	KNApSAcK
Pancratium biflorum	Plant	KNApSAcK
Sprekelia formosissima	Plant	KNApSAcK
Sternbergia lutea	LOTUS Database	35616633
Zephyranthes candida	Plant	KNApSAcK
Zephyranthes carinata	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

alkaloid (CHEBI:8402 )

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	0.73	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

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB005931

KNApSAcK ID

C00001580

Chemspider ID

Not Available

KEGG Compound ID

C08536

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

73360

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Pretazettine (NP0046792)

MOL for NP0046792 (Pretazettine)

3D MOL for NP0046792 (Pretazettine)

3D SDF for NP0046792 (Pretazettine)

3D-SDF for NP0046792 (Pretazettine)

PDB for NP0046792 (Pretazettine)

3D PDB for NP0046792 (Pretazettine)

SMILES for NP0046792 (Pretazettine)

INCHI for NP0046792 (Pretazettine)

Structure for NP0046792 (Pretazettine)

3D Structure for NP0046792 (Pretazettine)