NP-MRD: Showing NP-Card for (1s,13s,15r,18r)-15-{[(3s)-3-hydroxybutanoyl]oxy}-5,7-dioxa-12-azapentacyclo[10.5.2.0¹,¹³.0²,¹⁰.0⁴,⁸]nonadeca-2,4(8),9,16-tetraen-18-yl (2e)-but-2-enoate (NP0214620)

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Record Information

Version

2.0

Created at

2022-09-05 13:58:20 UTC

Updated at

2022-09-05 13:58:20 UTC

NP-MRD ID

NP0214620

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,13s,15r,18r)-15-{[(3s)-3-hydroxybutanoyl]oxy}-5,7-dioxa-12-azapentacyclo[10.5.2.0¹,¹³.0²,¹⁰.0⁴,⁸]nonadeca-2,4(8),9,16-tetraen-18-yl (2e)-but-2-enoate

Description

(1S,13S,15R,18R)-15-{[(3S)-3-hydroxybutanoyl]oxy}-5,7-dioxa-12-azapentacyclo[10.5.2.0¹,¹³.0²,¹⁰.0⁴,⁸]Nonadeca-2,4(8),9,16-tetraen-18-yl (2E)-but-2-enoate 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. (1s,13s,15r,18r)-15-{[(3s)-3-hydroxybutanoyl]oxy}-5,7-dioxa-12-azapentacyclo[10.5.2.0¹,¹³.0²,¹⁰.0⁴,⁸]nonadeca-2,4(8),9,16-tetraen-18-yl (2e)-but-2-enoate is found in Galanthus nivalis. Based on a literature review very few articles have been published on (1S,13S,15R,18R)-15-{[(3S)-3-hydroxybutanoyl]oxy}-5,7-dioxa-12-azapentacyclo[10.5.2.0¹,¹³.0²,¹⁰.0⁴,⁸]Nonadeca-2,4(8),9,16-tetraen-18-yl (2E)-but-2-enoate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309052215582D          

 32 36  0  0  1  0            999 V2000
   -1.9018    3.0531    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3468    2.4427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5980    1.6569    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0430    1.0464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2941    0.2606    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2368    1.2219    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3182    0.6115    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0090   -0.1534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

     RDKit          3D

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M  END


  Mrv1652309052215582D          

 32 36  0  0  1  0            999 V2000
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M  END
> <DATABASE_ID>
NP0214620

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C24H27NO7/c1-3-4-22(27)32-21-12-25-11-15-8-18-19(30-13-29-18)10-17(15)24(21)6-5-16(9-20(24)25)31-23(28)7-14(2)26/h3-6,8,10,14,16,20-21,26H,7,9,11-13H2,1-2H3/b4-3+/t14-,16-,20-,21-,24-/m0/s1

> <INCHI_KEY>
JBUJLIZQYREJLN-HAVIJFIKSA-N

> <FORMULA>
C24H27NO7

> <MOLECULAR_WEIGHT>
441.48

> <EXACT_MASS>
441.178752213

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
59

> <JCHEM_AVERAGE_POLARIZABILITY>
45.896488134248195

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,13S,15R,18R)-15-{[(3S)-3-hydroxybutanoyl]oxy}-5,7-dioxa-12-azapentacyclo[10.5.2.0^{1,13}.0^{2,10}.0^{4,8}]nonadeca-2,4(8),9,16-tetraen-18-yl (2E)-but-2-enoate

> <JCHEM_LOGP>
2.277474526333334

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.407199715528243

> <JCHEM_PKA_STRONGEST_BASIC>
7.879225157048153

> <JCHEM_POLAR_SURFACE_AREA>
94.53

> <JCHEM_REFRACTIVITY>
115.79750000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1S,13S,15R,18R)-15-{[(3S)-3-hydroxybutanoyl]oxy}-5,7-dioxa-12-azapentacyclo[10.5.2.0^{1,13}.0^{2,10}.0^{4,8}]nonadeca-2,4(8),9,16-tetraen-18-yl (2E)-but-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 05-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-SEP-22         0                                  
HETATM    1  C   UNK     0      -3.550   5.699   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.514   4.560   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.983   3.093   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.947   1.953   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      -2.416   0.486   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0      -0.442   2.281   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       0.594   1.141   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.017  -0.286   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0       0.773  -1.628   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0       2.294  -1.873   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.625  -0.940   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.814  -1.519   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.095  -0.664   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.995   0.872   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.718   1.746   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.334   0.700   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.070   1.580   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.498   2.158   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.712   1.210   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.498  -0.315   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       5.712  -1.262   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       5.498  -2.787   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       4.071  -3.365   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       6.712  -3.735   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       6.499  -5.260   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       7.713  -6.207   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       5.071  -5.838   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       3.070  -0.892   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       1.856   0.055   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       7.426   1.442   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       8.410   0.257   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       7.587  -1.045   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6    8   17                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   29                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   16                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   32                                                  
CONECT   14   13   15   30                                                  
CONECT   15   14   16                                                       
CONECT   16   15   11   17                                                  
CONECT   17   16    7   18   29                                             
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21   28                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25                                                       
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25                                                            
CONECT   28   20   29                                                       
CONECT   29   28    9   17                                                  
CONECT   30   14   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   13                                                       
MASTER        0    0    0    0    0    0    0    0   32    0   72    0
END

View in JSmol

Synonyms

Value	Source
(1S,13S,15R,18R)-15-{[(3S)-3-hydroxybutanoyl]oxy}-5,7-dioxa-12-azapentacyclo[10.5.2.0,.0,.0,]nonadeca-2,4(8),9,16-tetraen-18-yl (2E)-but-2-enoic acid	Generator

Chemical Formula

C₂₄H₂₇NO₇

Average Mass

441.4800 Da

Monoisotopic Mass

441.17875 Da

IUPAC Name

(1S,13S,15R,18R)-15-{[(3S)-3-hydroxybutanoyl]oxy}-5,7-dioxa-12-azapentacyclo[10.5.2.0^{1,13}.0^{2,10}.0^{4,8}]nonadeca-2,4(8),9,16-tetraen-18-yl (2E)-but-2-enoate

Traditional Name

(1S,13S,15R,18R)-15-{[(3S)-3-hydroxybutanoyl]oxy}-5,7-dioxa-12-azapentacyclo[10.5.2.0^{1,13}.0^{2,10}.0^{4,8}]nonadeca-2,4(8),9,16-tetraen-18-yl (2E)-but-2-enoate

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C24H27NO7/c1-3-4-22(27)32-21-12-25-11-15-8-18-19(30-13-29-18)10-17(15)24(21)6-5-16(9-20(24)25)31-23(28)7-14(2)26/h3-6,8,10,14,16,20-21,26H,7,9,11-13H2,1-2H3/b4-3+/t14-,16-,20-,21-,24-/m0/s1

InChI Key

JBUJLIZQYREJLN-HAVIJFIKSA-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, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, 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
Galanthus nivalis	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
Indole or derivatives
Benzodioxole
Azepine
Beta-hydroxy acid
Fatty acid ester
Aralkylamine
N-alkylpyrrolidine
Benzenoid
Dicarboxylic acid or derivatives
Hydroxy acid
Fatty acyl
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Pyrrolidine
Secondary alcohol
Tertiary amine
Tertiary aliphatic amine
Carboxylic acid ester
Amino acid or derivatives
Acetal
Oxacycle
Carboxylic acid derivative
Azacycle
Organoheterocyclic compound
Carbonyl group
Alcohol
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic oxygen compound
Amine
Organic nitrogen compound
Organooxygen compound
Organonitrogen compound
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	2.28	ChemAxon
pKa (Strongest Acidic)	15.41	ChemAxon
pKa (Strongest Basic)	7.88	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	94.53 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	115.8 m³·mol⁻¹	ChemAxon
Polarizability	45.9 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	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

163191047

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1s,13s,15r,18r)-15-{[(3s)-3-hydroxybutanoyl]oxy}-5,7-dioxa-12-azapentacyclo[10.5.2.0¹,¹³.0²,¹⁰.0⁴,⁸]nonadeca-2,4(8),9,16-tetraen-18-yl (2e)-but-2-enoate (NP0214620)

MOL for NP0214620 ((1s,13s,15r,18r)-15-{[(3s)-3-hydroxybutanoyl]oxy}-5,7-dioxa-12-azapentacyclo[10.5.2.0¹,¹³.0²,¹⁰.0⁴,⁸]nonadeca-2,4(8),9,16-tetraen-18-yl (2e)-but-2-enoate)

3D MOL for NP0214620 ((1s,13s,15r,18r)-15-{[(3s)-3-hydroxybutanoyl]oxy}-5,7-dioxa-12-azapentacyclo[10.5.2.0¹,¹³.0²,¹⁰.0⁴,⁸]nonadeca-2,4(8),9,16-tetraen-18-yl (2e)-but-2-enoate)

3D SDF for NP0214620 ((1s,13s,15r,18r)-15-{[(3s)-3-hydroxybutanoyl]oxy}-5,7-dioxa-12-azapentacyclo[10.5.2.0¹,¹³.0²,¹⁰.0⁴,⁸]nonadeca-2,4(8),9,16-tetraen-18-yl (2e)-but-2-enoate)

3D-SDF for NP0214620 ((1s,13s,15r,18r)-15-{[(3s)-3-hydroxybutanoyl]oxy}-5,7-dioxa-12-azapentacyclo[10.5.2.0¹,¹³.0²,¹⁰.0⁴,⁸]nonadeca-2,4(8),9,16-tetraen-18-yl (2e)-but-2-enoate)

PDB for NP0214620 ((1s,13s,15r,18r)-15-{[(3s)-3-hydroxybutanoyl]oxy}-5,7-dioxa-12-azapentacyclo[10.5.2.0¹,¹³.0²,¹⁰.0⁴,⁸]nonadeca-2,4(8),9,16-tetraen-18-yl (2e)-but-2-enoate)

3D PDB for NP0214620 ((1s,13s,15r,18r)-15-{[(3s)-3-hydroxybutanoyl]oxy}-5,7-dioxa-12-azapentacyclo[10.5.2.0¹,¹³.0²,¹⁰.0⁴,⁸]nonadeca-2,4(8),9,16-tetraen-18-yl (2e)-but-2-enoate)

SMILES for NP0214620 ((1s,13s,15r,18r)-15-{[(3s)-3-hydroxybutanoyl]oxy}-5,7-dioxa-12-azapentacyclo[10.5.2.0¹,¹³.0²,¹⁰.0⁴,⁸]nonadeca-2,4(8),9,16-tetraen-18-yl (2e)-but-2-enoate)

INCHI for NP0214620 ((1s,13s,15r,18r)-15-{[(3s)-3-hydroxybutanoyl]oxy}-5,7-dioxa-12-azapentacyclo[10.5.2.0¹,¹³.0²,¹⁰.0⁴,⁸]nonadeca-2,4(8),9,16-tetraen-18-yl (2e)-but-2-enoate)

Structure for NP0214620 ((1s,13s,15r,18r)-15-{[(3s)-3-hydroxybutanoyl]oxy}-5,7-dioxa-12-azapentacyclo[10.5.2.0¹,¹³.0²,¹⁰.0⁴,⁸]nonadeca-2,4(8),9,16-tetraen-18-yl (2e)-but-2-enoate)

3D Structure for NP0214620 ((1s,13s,15r,18r)-15-{[(3s)-3-hydroxybutanoyl]oxy}-5,7-dioxa-12-azapentacyclo[10.5.2.0¹,¹³.0²,¹⁰.0⁴,⁸]nonadeca-2,4(8),9,16-tetraen-18-yl (2e)-but-2-enoate)