NP-MRD: Showing NP-Card for 3-({4-[2,3-dihydroxy-1-(4-hydroxy-3,5-dimethoxyphenyl)propoxy]phenyl}methyl)-1-hydroxy-3h,6h,7h,8h,8ah-pyrrolo[1,2-a]pyrazin-4-one (NP0293379)

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Record Information

Version

2.0

Created at

2022-09-10 01:21:17 UTC

Updated at

2022-09-10 01:21:17 UTC

NP-MRD ID

NP0293379

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3-({4-[2,3-dihydroxy-1-(4-hydroxy-3,5-dimethoxyphenyl)propoxy]phenyl}methyl)-1-hydroxy-3h,6h,7h,8h,8ah-pyrrolo[1,2-a]pyrazin-4-one

Description

3-({4-[2,3-Dihydroxy-1-(4-hydroxy-3,5-dimethoxyphenyl)propoxy]phenyl}methyl)-1-hydroxy-3H,4H,6H,7H,8H,8aH-pyrrolo[1,2-a]pyrazin-4-one belongs to the class of organic compounds known as methoxyphenols. Methoxyphenols are compounds containing a methoxy group attached to the benzene ring of a phenol moiety. 3-({4-[2,3-dihydroxy-1-(4-hydroxy-3,5-dimethoxyphenyl)propoxy]phenyl}methyl)-1-hydroxy-3h,6h,7h,8h,8ah-pyrrolo[1,2-a]pyrazin-4-one is found in Eleutherococcus senticosus. 3-({4-[2,3-Dihydroxy-1-(4-hydroxy-3,5-dimethoxyphenyl)propoxy]phenyl}methyl)-1-hydroxy-3H,4H,6H,7H,8H,8aH-pyrrolo[1,2-a]pyrazin-4-one is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004171509532D          

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M  END

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  Mrv1533004171509532D          

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M  END
> <DATABASE_ID>
NP0293379

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(=CC(OC)=C1O)C(OC1=CC=C(CC2NC(=O)C3CCCN3C2=O)C=C1)C(O)CO

> <INCHI_IDENTIFIER>
InChI=1S/C25H30N2O8/c1-33-20-11-15(12-21(34-2)22(20)30)23(19(29)13-28)35-16-7-5-14(6-8-16)10-17-25(32)27-9-3-4-18(27)24(31)26-17/h5-8,11-12,17-19,23,28-30H,3-4,9-10,13H2,1-2H3,(H,26,31)

> <INCHI_KEY>
KEHHDVAPJYKAGP-UHFFFAOYSA-N

> <FORMULA>
C25H30N2O8

> <MOLECULAR_WEIGHT>
486.521

> <EXACT_MASS>
486.200215934

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
65

> <JCHEM_AVERAGE_POLARIZABILITY>
49.19993881433146

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-({4-[2,3-dihydroxy-1-(4-hydroxy-3,5-dimethoxyphenyl)propoxy]phenyl}methyl)-octahydropyrrolo[1,2-a]piperazine-1,4-dione

> <ALOGPS_LOGP>
1.46

> <JCHEM_LOGP>
0.5431780653333335

> <ALOGPS_LOGS>
-2.98

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
10.784078214516647

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.283740877070818

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9779509873448404

> <JCHEM_POLAR_SURFACE_AREA>
137.79000000000002

> <JCHEM_REFRACTIVITY>
124.81099999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.11e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-({4-[2,3-dihydroxy-1-(4-hydroxy-3,5-dimethoxyphenyl)propoxy]phenyl}methyl)-hexahydropyrrolo[1,2-a]piperazine-1,4-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 17-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-APR-15         0                                  
HETATM    1  C   UNK     0       8.925  17.473   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       8.925  15.933   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       7.591  15.163   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.591  13.623   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.258  12.853   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.924  13.623   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.924  15.163   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       3.590  15.933   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       3.590  17.473   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.258  15.933   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       6.258  17.473   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       6.258  11.313   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       7.591  10.543   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       7.591   9.003   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.925   8.233   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.925   6.693   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       7.591   5.923   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       7.591   4.383   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.258   3.613   0.000  0.00  0.00           C+0
HETATM   20  N   UNK     0       6.258   2.073   0.000  0.00  0.00           N+0
HETATM   21  C   UNK     0       4.924   1.303   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       4.924  -0.237   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       3.590   2.073   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       2.126   1.597   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       1.220   2.843   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       2.126   4.089   0.000  0.00  0.00           C+0
HETATM   27  N   UNK     0       3.590   3.613   0.000  0.00  0.00           N+0
HETATM   28  C   UNK     0       4.924   4.383   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       4.924   5.923   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       6.258   6.693   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       6.258   8.233   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       4.924  10.543   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       3.590  11.313   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       4.924   9.003   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0       3.590   8.233   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   10                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   12                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   10                                                  
CONECT    8    7    9                                                       
CONECT    9    8                                                            
CONECT   10    7    3   11                                                  
CONECT   11   10                                                            
CONECT   12    5   13   32                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   31                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   30                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20   28                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24   27                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   23   28                                                  
CONECT   28   27   19   29                                                  
CONECT   29   28                                                            
CONECT   30   17   31                                                       
CONECT   31   30   14                                                       
CONECT   32   12   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32   35                                                       
CONECT   35   34                                                            
MASTER        0    0    0    0    0    0    0    0   35    0   76    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₅H₃₀N₂O₈

Average Mass

486.5210 Da

Monoisotopic Mass

486.20022 Da

IUPAC Name

3-({4-[2,3-dihydroxy-1-(4-hydroxy-3,5-dimethoxyphenyl)propoxy]phenyl}methyl)-octahydropyrrolo[1,2-a]piperazine-1,4-dione

Traditional Name

3-({4-[2,3-dihydroxy-1-(4-hydroxy-3,5-dimethoxyphenyl)propoxy]phenyl}methyl)-hexahydropyrrolo[1,2-a]piperazine-1,4-dione

CAS Registry Number

Not Available

SMILES

COC1=CC(=CC(OC)=C1O)C(OC1=CC=C(CC2NC(=O)C3CCCN3C2=O)C=C1)C(O)CO

InChI Identifier

InChI=1S/C25H30N2O8/c1-33-20-11-15(12-21(34-2)22(20)30)23(19(29)13-28)35-16-7-5-14(6-8-16)10-17-25(32)27-9-3-4-18(27)24(31)26-17/h5-8,11-12,17-19,23,28-30H,3-4,9-10,13H2,1-2H3,(H,26,31)

InChI Key

KEHHDVAPJYKAGP-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
Eleutherococcus senticosus	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as methoxyphenols. Methoxyphenols are compounds containing a methoxy group attached to the benzene ring of a phenol moiety.

Kingdom

Super Class

Class

Sub Class

Direct Parent

Alternative Parents

Substituents

Alpha-amino acid or derivatives
Methoxyphenol
M-dimethoxybenzene
Dimethoxybenzene
Phenoxy compound
Anisole
Dioxopiperazine
Phenol ether
Methoxybenzene
2,5-dioxopiperazine
Alkyl aryl ether
N-alkylpiperazine
Monocyclic benzene moiety
1,4-diazinane
Piperazine
Pyrrolidine
Tertiary carboxylic acid amide
Secondary alcohol
Secondary carboxylic acid amide
1,2-diol
Carboxamide group
Lactam
Organoheterocyclic compound
Azacycle
Ether
Carboxylic acid derivative
Primary alcohol
Alcohol
Organic oxide
Hydrocarbon derivative
Carbonyl group
Organonitrogen compound
Organopnictogen compound
Organic oxygen compound
Organooxygen compound
Organic nitrogen 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	1.46	ALOGPS
logP	0.54	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	9.28	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	137.79 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	124.81 m³·mol⁻¹	ChemAxon
Polarizability	49.2 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 3-({4-[2,3-dihydroxy-1-(4-hydroxy-3,5-dimethoxyphenyl)propoxy]phenyl}methyl)-1-hydroxy-3h,6h,7h,8h,8ah-pyrrolo[1,2-a]pyrazin-4-one (NP0293379)

MOL for NP0293379 (3-({4-[2,3-dihydroxy-1-(4-hydroxy-3,5-dimethoxyphenyl)propoxy]phenyl}methyl)-1-hydroxy-3h,6h,7h,8h,8ah-pyrrolo[1,2-a]pyrazin-4-one)

3D MOL for NP0293379 (3-({4-[2,3-dihydroxy-1-(4-hydroxy-3,5-dimethoxyphenyl)propoxy]phenyl}methyl)-1-hydroxy-3h,6h,7h,8h,8ah-pyrrolo[1,2-a]pyrazin-4-one)

3D SDF for NP0293379 (3-({4-[2,3-dihydroxy-1-(4-hydroxy-3,5-dimethoxyphenyl)propoxy]phenyl}methyl)-1-hydroxy-3h,6h,7h,8h,8ah-pyrrolo[1,2-a]pyrazin-4-one)

3D-SDF for NP0293379 (3-({4-[2,3-dihydroxy-1-(4-hydroxy-3,5-dimethoxyphenyl)propoxy]phenyl}methyl)-1-hydroxy-3h,6h,7h,8h,8ah-pyrrolo[1,2-a]pyrazin-4-one)

PDB for NP0293379 (3-({4-[2,3-dihydroxy-1-(4-hydroxy-3,5-dimethoxyphenyl)propoxy]phenyl}methyl)-1-hydroxy-3h,6h,7h,8h,8ah-pyrrolo[1,2-a]pyrazin-4-one)

3D PDB for NP0293379 (3-({4-[2,3-dihydroxy-1-(4-hydroxy-3,5-dimethoxyphenyl)propoxy]phenyl}methyl)-1-hydroxy-3h,6h,7h,8h,8ah-pyrrolo[1,2-a]pyrazin-4-one)

SMILES for NP0293379 (3-({4-[2,3-dihydroxy-1-(4-hydroxy-3,5-dimethoxyphenyl)propoxy]phenyl}methyl)-1-hydroxy-3h,6h,7h,8h,8ah-pyrrolo[1,2-a]pyrazin-4-one)

INCHI for NP0293379 (3-({4-[2,3-dihydroxy-1-(4-hydroxy-3,5-dimethoxyphenyl)propoxy]phenyl}methyl)-1-hydroxy-3h,6h,7h,8h,8ah-pyrrolo[1,2-a]pyrazin-4-one)

Structure for NP0293379 (3-({4-[2,3-dihydroxy-1-(4-hydroxy-3,5-dimethoxyphenyl)propoxy]phenyl}methyl)-1-hydroxy-3h,6h,7h,8h,8ah-pyrrolo[1,2-a]pyrazin-4-one)

3D Structure for NP0293379 (3-({4-[2,3-dihydroxy-1-(4-hydroxy-3,5-dimethoxyphenyl)propoxy]phenyl}methyl)-1-hydroxy-3h,6h,7h,8h,8ah-pyrrolo[1,2-a]pyrazin-4-one)