NP-MRD: Showing NP-Card for octahydro-1h-quinolizin-1-ylmethyl 3-{3-methoxy-4-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]phenyl}prop-2-enoate (NP0240807)

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Record Information

Version

2.0

Created at

2022-09-07 00:43:06 UTC

Updated at

2022-09-07 00:43:06 UTC

NP-MRD ID

NP0240807

Secondary Accession Numbers

None

Natural Product Identification

Common Name

octahydro-1h-quinolizin-1-ylmethyl 3-{3-methoxy-4-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]phenyl}prop-2-enoate

Description

(Octahydro-1H-quinolizin-1-yl)methyl 3-{3-methoxy-4-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]phenyl}prop-2-enoate belongs to the class of organic compounds known as phenolic glycosides. These are organic compounds containing a phenolic structure attached to a glycosyl moiety. Some examples of phenolic structures include lignans, and flavonoids. octahydro-1h-quinolizin-1-ylmethyl 3-{3-methoxy-4-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]phenyl}prop-2-enoate is found in Lupinus angustifolius and Lupinus pilosus. Among the sugar units found in natural glycosides are D-glucose, L-Fructose, and L rhamnose (octahydro-1H-quinolizin-1-yl)methyl 3-{3-methoxy-4-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]phenyl}prop-2-enoate is a very strong basic compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004161508332D          

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M  END

     RDKit          3D

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M  END


  Mrv1533004161508332D          

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  5 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
  3 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 28 30  1  0  0  0  0
 30 31  1  0  0  0  0
 30 32  1  0  0  0  0
 32 33  1  0  0  0  0
 32 34  1  0  0  0  0
 26 34  1  0  0  0  0
 34 35  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0240807

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(C=CC(=O)OCC2CCCN3CCCCC23)=CC=C1OC1OC(C)C(O)C(O)C1O

> <INCHI_IDENTIFIER>
InChI=1S/C26H37NO8/c1-16-23(29)24(30)25(31)26(34-16)35-20-10-8-17(14-21(20)32-2)9-11-22(28)33-15-18-6-5-13-27-12-4-3-7-19(18)27/h8-11,14,16,18-19,23-26,29-31H,3-7,12-13,15H2,1-2H3

> <INCHI_KEY>
QVWPBWPQLTYKFZ-UHFFFAOYSA-N

> <FORMULA>
C26H37NO8

> <MOLECULAR_WEIGHT>
491.581

> <EXACT_MASS>
491.251917155

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
72

> <JCHEM_AVERAGE_POLARIZABILITY>
53.90219782981868

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(octahydro-1H-quinolizin-1-yl)methyl 3-{3-methoxy-4-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]phenyl}prop-2-enoate

> <ALOGPS_LOGP>
2.31

> <JCHEM_LOGP>
2.2720157396666663

> <ALOGPS_LOGS>
-3.22

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
13.268671603378476

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.213966922619974

> <JCHEM_PKA_STRONGEST_BASIC>
9.291911322419333

> <JCHEM_POLAR_SURFACE_AREA>
117.92000000000002

> <JCHEM_REFRACTIVITY>
128.85630000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.97e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
octahydro-1H-quinolizin-1-ylmethyl 3-{3-methoxy-4-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]phenyl}prop-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 16-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   16-APR-15         0                                  
HETATM    1  C   UNK     0       6.668 -14.630   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       8.002 -13.860   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       8.002 -12.320   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.668 -11.550   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.668 -10.010   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.335  -9.240   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.335  -7.700   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       2.667  -7.700   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0       4.001  -5.390   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   16  N   UNK     0       4.001  -0.770   0.000  0.00  0.00           N+0
HETATM   17  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       8.002  -9.240   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       9.336 -10.010   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       9.336 -11.550   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      10.669 -12.320   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      10.669 -13.860   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       9.336 -14.630   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       9.336 -16.170   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       8.002 -16.940   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      10.669 -16.940   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      10.669 -18.480   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      12.003 -16.170   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      13.337 -16.940   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0      12.003 -14.630   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0      13.337 -13.860   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   24                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   22                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   21                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   21                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   12   16                                                  
CONECT   22    5   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23    3   25                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27   34                                                  
CONECT   27   26   28                                                       
CONECT   28   27   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32   26   35                                                  
CONECT   35   34                                                            
MASTER        0    0    0    0    0    0    0    0   35    0   76    0
END

View in JSmol

Synonyms

Value	Source
(Octahydro-1H-quinolizin-1-yl)methyl 3-{3-methoxy-4-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]phenyl}prop-2-enoic acid	Generator

Chemical Formula

C₂₆H₃₇NO₈

Average Mass

491.5810 Da

Monoisotopic Mass

491.25192 Da

IUPAC Name

(octahydro-1H-quinolizin-1-yl)methyl 3-{3-methoxy-4-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]phenyl}prop-2-enoate

Traditional Name

octahydro-1H-quinolizin-1-ylmethyl 3-{3-methoxy-4-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]phenyl}prop-2-enoate

CAS Registry Number

Not Available

SMILES

COC1=CC(C=CC(=O)OCC2CCCN3CCCCC23)=CC=C1OC1OC(C)C(O)C(O)C1O

InChI Identifier

InChI=1S/C26H37NO8/c1-16-23(29)24(30)25(31)26(34-16)35-20-10-8-17(14-21(20)32-2)9-11-22(28)33-15-18-6-5-13-27-12-4-3-7-19(18)27/h8-11,14,16,18-19,23-26,29-31H,3-7,12-13,15H2,1-2H3

InChI Key

QVWPBWPQLTYKFZ-UHFFFAOYSA-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
Lupinus angustifolius	LOTUS Database	35616633
Lupinus pilosus	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenolic glycosides. These are organic compounds containing a phenolic structure attached to a glycosyl moiety. Some examples of phenolic structures include lignans, and flavonoids. Among the sugar units found in natural glycosides are D-glucose, L-Fructose, and L rhamnose.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Phenolic glycosides

Alternative Parents

Substituents

Phenolic glycoside
Cinnamic acid ester
Cinnamic acid or derivatives
Coumaric acid or derivatives
Hexose monosaccharide
Lupinine
O-glycosyl compound
Quinolizine
Quinolizidine
Alkaloid or derivatives
Styrene
Phenol ether
Anisole
Phenoxy compound
Methoxybenzene
Fatty acid ester
Alkyl aryl ether
Monocyclic benzene moiety
Fatty acyl
Monosaccharide
Oxane
Benzenoid
Piperidine
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Tertiary amine
Amino acid or derivatives
Tertiary aliphatic amine
Secondary alcohol
Carboxylic acid ester
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Azacycle
Oxacycle
Ether
Polyol
Acetal
Carboxylic acid derivative
Organopnictogen compound
Carbonyl group
Organic oxide
Hydrocarbon derivative
Alcohol
Organic nitrogen compound
Organonitrogen compound
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	2.31	ALOGPS
logP	2.27	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	12.21	ChemAxon
pKa (Strongest Basic)	9.29	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	117.92 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	128.86 m³·mol⁻¹	ChemAxon
Polarizability	53.9 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for octahydro-1h-quinolizin-1-ylmethyl 3-{3-methoxy-4-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]phenyl}prop-2-enoate (NP0240807)

MOL for NP0240807 (octahydro-1h-quinolizin-1-ylmethyl 3-{3-methoxy-4-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]phenyl}prop-2-enoate)

3D MOL for NP0240807 (octahydro-1h-quinolizin-1-ylmethyl 3-{3-methoxy-4-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]phenyl}prop-2-enoate)

3D SDF for NP0240807 (octahydro-1h-quinolizin-1-ylmethyl 3-{3-methoxy-4-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]phenyl}prop-2-enoate)

3D-SDF for NP0240807 (octahydro-1h-quinolizin-1-ylmethyl 3-{3-methoxy-4-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]phenyl}prop-2-enoate)

PDB for NP0240807 (octahydro-1h-quinolizin-1-ylmethyl 3-{3-methoxy-4-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]phenyl}prop-2-enoate)

3D PDB for NP0240807 (octahydro-1h-quinolizin-1-ylmethyl 3-{3-methoxy-4-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]phenyl}prop-2-enoate)

SMILES for NP0240807 (octahydro-1h-quinolizin-1-ylmethyl 3-{3-methoxy-4-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]phenyl}prop-2-enoate)

INCHI for NP0240807 (octahydro-1h-quinolizin-1-ylmethyl 3-{3-methoxy-4-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]phenyl}prop-2-enoate)

Structure for NP0240807 (octahydro-1h-quinolizin-1-ylmethyl 3-{3-methoxy-4-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]phenyl}prop-2-enoate)

3D Structure for NP0240807 (octahydro-1h-quinolizin-1-ylmethyl 3-{3-methoxy-4-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]phenyl}prop-2-enoate)