NP-MRD: Showing NP-Card for 1,8a-dihydroxy-3-{[2-hydroxy-7,7-dimethyl-3-(2-methylbut-3-en-2-yl)chromeno[5,6-b]pyrrol-3-yl]methyl}-3h,6h,7h,8h-pyrrolo[1,2-a]pyrazin-4-one (NP0283611)

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Record Information

Version

2.0

Created at

2022-09-09 10:56:55 UTC

Updated at

2022-09-09 10:56:55 UTC

NP-MRD ID

NP0283611

Secondary Accession Numbers

None

Natural Product Identification

Common Name

1,8a-dihydroxy-3-{[2-hydroxy-7,7-dimethyl-3-(2-methylbut-3-en-2-yl)chromeno[5,6-b]pyrrol-3-yl]methyl}-3h,6h,7h,8h-pyrrolo[1,2-a]pyrazin-4-one

Description

1,8A-dihydroxy-3-{[2-hydroxy-7,7-dimethyl-3-(2-methylbut-3-en-2-yl)-3H,7H-chromeno[5,6-b]pyrrol-3-yl]methyl}-3H,4H,6H,7H,8H,8aH-pyrrolo[1,2-a]pyrazin-4-one belongs to the class of organic compounds known as 2,2-dimethyl-1-benzopyrans. These are organic compounds containing a 1-benzopyran moiety that carries two methyl groups at the 2-position. 1,8A-dihydroxy-3-{[2-hydroxy-7,7-dimethyl-3-(2-methylbut-3-en-2-yl)-3H,7H-chromeno[5,6-b]pyrrol-3-yl]methyl}-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


  Mrv1533004251508072D          

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M  END

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M  END


  Mrv1533004251508072D          

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M  END
> <DATABASE_ID>
NP0283611

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)(C=C)C1(CC2NC(=O)C3(O)CCCN3C2=O)C(=O)NC2=C3C=CC(C)(C)OC3=CC=C12

> <INCHI_IDENTIFIER>
InChI=1S/C26H31N3O5/c1-6-23(2,3)25(14-17-20(30)29-13-7-11-26(29,33)22(32)27-17)16-8-9-18-15(19(16)28-21(25)31)10-12-24(4,5)34-18/h6,8-10,12,17,33H,1,7,11,13-14H2,2-5H3,(H,27,32)(H,28,31)

> <INCHI_KEY>
GRGBTCMGCXJTOO-UHFFFAOYSA-N

> <FORMULA>
C26H31N3O5

> <MOLECULAR_WEIGHT>
465.55

> <EXACT_MASS>
465.22637111

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
65

> <JCHEM_AVERAGE_POLARIZABILITY>
49.255999943788936

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-{[7,7-dimethyl-3-(2-methylbut-3-en-2-yl)-2-oxo-1H,2H,3H,7H-chromeno[5,6-b]pyrrol-3-yl]methyl}-8a-hydroxy-octahydropyrrolo[1,2-a]piperazine-1,4-dione

> <ALOGPS_LOGP>
2.57

> <JCHEM_LOGP>
2.3469801846666662

> <ALOGPS_LOGS>
-4.29

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
11.875457530531659

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.45968309273311

> <JCHEM_PKA_STRONGEST_BASIC>
-3.498792689099995

> <JCHEM_POLAR_SURFACE_AREA>
107.97000000000001

> <JCHEM_REFRACTIVITY>
128.7801

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.40e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-{[7,7-dimethyl-3-(2-methylbut-3-en-2-yl)-2-oxo-1H-chromeno[5,6-b]pyrrol-3-yl]methyl}-8a-hydroxy-tetrahydro-2H-pyrrolo[1,2-a]piperazine-1,4-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 25-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   25-APR-15         0                                  
HETATM    1  C   UNK     0      -1.264  -5.776   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.261  -5.984   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.787  -6.193   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.053  -7.510   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.373  -8.092   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.470  -4.459   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.069  -4.410   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.797  -3.053   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0      -0.986  -1.744   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0      -1.714  -0.387   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -0.902   0.922   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      -3.253  -0.339   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -2.583   1.047   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      -4.247   0.837   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -5.673   0.255   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -5.560  -1.281   0.000  0.00  0.00           C+0
HETATM   17  N   UNK     0      -4.064  -1.648   0.000  0.00  0.00           N+0
HETATM   18  C   UNK     0      -3.336  -3.005   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -4.148  -4.314   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       0.357  -2.923   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      -0.225  -1.497   0.000  0.00  0.00           O+0
HETATM   22  N   UNK     0       1.783  -2.341   0.000  0.00  0.00           N+0
HETATM   23  C   UNK     0       2.777  -3.517   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       4.316  -3.565   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       5.128  -2.256   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       6.667  -2.304   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       7.395  -3.661   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       8.543  -4.687   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       8.605  -2.708   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       6.584  -4.970   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       5.044  -4.922   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       4.233  -6.231   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       2.694  -6.183   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       1.966  -4.826   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4    6                                             
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4                                                            
CONECT    6    2    7   20   34                                             
CONECT    7    6    8                                                       
CONECT    8    7    9   18                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13   14   17                                             
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   12   18                                                  
CONECT   18   17    8   19                                                  
CONECT   19   18                                                            
CONECT   20    6   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23                                                       
CONECT   23   22   24   34                                                  
CONECT   24   23   25   31                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28   29   30                                             
CONECT   28   27                                                            
CONECT   29   27                                                            
CONECT   30   27   31                                                       
CONECT   31   30   24   32                                                  
CONECT   32   31   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33    6   23                                                  
MASTER        0    0    0    0    0    0    0    0   34    0   76    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₆H₃₁N₃O₅

Average Mass

465.5500 Da

Monoisotopic Mass

465.22637 Da

IUPAC Name

3-{[7,7-dimethyl-3-(2-methylbut-3-en-2-yl)-2-oxo-1H,2H,3H,7H-chromeno[5,6-b]pyrrol-3-yl]methyl}-8a-hydroxy-octahydropyrrolo[1,2-a]piperazine-1,4-dione

Traditional Name

3-{[7,7-dimethyl-3-(2-methylbut-3-en-2-yl)-2-oxo-1H-chromeno[5,6-b]pyrrol-3-yl]methyl}-8a-hydroxy-tetrahydro-2H-pyrrolo[1,2-a]piperazine-1,4-dione

CAS Registry Number

Not Available

SMILES

CC(C)(C=C)C1(CC2NC(=O)C3(O)CCCN3C2=O)C(=O)NC2=C3C=CC(C)(C)OC3=CC=C12

InChI Identifier

InChI=1S/C26H31N3O5/c1-6-23(2,3)25(14-17-20(30)29-13-7-11-26(29,33)22(32)27-17)16-8-9-18-15(19(16)28-21(25)31)10-12-24(4,5)34-18/h6,8-10,12,17,33H,1,7,11,13-14H2,2-5H3,(H,27,32)(H,28,31)

InChI Key

GRGBTCMGCXJTOO-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

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 2,2-dimethyl-1-benzopyrans. These are organic compounds containing a 1-benzopyran moiety that carries two methyl groups at the 2-position.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzopyrans

Sub Class

1-benzopyrans

Direct Parent

2,2-dimethyl-1-benzopyrans

Alternative Parents

Substituents

2,2-dimethyl-1-benzopyran
Alpha-amino acid or derivatives
3-alkylindole
Indole or derivatives
Alkyl aryl ether
Benzenoid
Pyrrolidine
Tertiary carboxylic acid amide
Cyclic carboximidic acid
Carboxamide group
Lactam
Azacycle
Oxacycle
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Alkanolamine
Carboxylic acid derivative
Ether
Organic oxygen compound
Organic oxide
Organonitrogen compound
Organooxygen compound
Carbonyl group
Organic nitrogen compound
Hydrocarbon derivative
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	2.57	ALOGPS
logP	2.35	ChemAxon
logS	-4.3	ALOGPS
pKa (Strongest Acidic)	10.46	ChemAxon
pKa (Strongest Basic)	-3.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	107.97 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	128.78 m³·mol⁻¹	ChemAxon
Polarizability	49.26 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

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

78144474

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 1,8a-dihydroxy-3-{[2-hydroxy-7,7-dimethyl-3-(2-methylbut-3-en-2-yl)chromeno[5,6-b]pyrrol-3-yl]methyl}-3h,6h,7h,8h-pyrrolo[1,2-a]pyrazin-4-one (NP0283611)

MOL for NP0283611 (1,8a-dihydroxy-3-{[2-hydroxy-7,7-dimethyl-3-(2-methylbut-3-en-2-yl)chromeno[5,6-b]pyrrol-3-yl]methyl}-3h,6h,7h,8h-pyrrolo[1,2-a]pyrazin-4-one)

3D MOL for NP0283611 (1,8a-dihydroxy-3-{[2-hydroxy-7,7-dimethyl-3-(2-methylbut-3-en-2-yl)chromeno[5,6-b]pyrrol-3-yl]methyl}-3h,6h,7h,8h-pyrrolo[1,2-a]pyrazin-4-one)

3D SDF for NP0283611 (1,8a-dihydroxy-3-{[2-hydroxy-7,7-dimethyl-3-(2-methylbut-3-en-2-yl)chromeno[5,6-b]pyrrol-3-yl]methyl}-3h,6h,7h,8h-pyrrolo[1,2-a]pyrazin-4-one)

3D-SDF for NP0283611 (1,8a-dihydroxy-3-{[2-hydroxy-7,7-dimethyl-3-(2-methylbut-3-en-2-yl)chromeno[5,6-b]pyrrol-3-yl]methyl}-3h,6h,7h,8h-pyrrolo[1,2-a]pyrazin-4-one)

PDB for NP0283611 (1,8a-dihydroxy-3-{[2-hydroxy-7,7-dimethyl-3-(2-methylbut-3-en-2-yl)chromeno[5,6-b]pyrrol-3-yl]methyl}-3h,6h,7h,8h-pyrrolo[1,2-a]pyrazin-4-one)

3D PDB for NP0283611 (1,8a-dihydroxy-3-{[2-hydroxy-7,7-dimethyl-3-(2-methylbut-3-en-2-yl)chromeno[5,6-b]pyrrol-3-yl]methyl}-3h,6h,7h,8h-pyrrolo[1,2-a]pyrazin-4-one)

SMILES for NP0283611 (1,8a-dihydroxy-3-{[2-hydroxy-7,7-dimethyl-3-(2-methylbut-3-en-2-yl)chromeno[5,6-b]pyrrol-3-yl]methyl}-3h,6h,7h,8h-pyrrolo[1,2-a]pyrazin-4-one)

INCHI for NP0283611 (1,8a-dihydroxy-3-{[2-hydroxy-7,7-dimethyl-3-(2-methylbut-3-en-2-yl)chromeno[5,6-b]pyrrol-3-yl]methyl}-3h,6h,7h,8h-pyrrolo[1,2-a]pyrazin-4-one)

Structure for NP0283611 (1,8a-dihydroxy-3-{[2-hydroxy-7,7-dimethyl-3-(2-methylbut-3-en-2-yl)chromeno[5,6-b]pyrrol-3-yl]methyl}-3h,6h,7h,8h-pyrrolo[1,2-a]pyrazin-4-one)

3D Structure for NP0283611 (1,8a-dihydroxy-3-{[2-hydroxy-7,7-dimethyl-3-(2-methylbut-3-en-2-yl)chromeno[5,6-b]pyrrol-3-yl]methyl}-3h,6h,7h,8h-pyrrolo[1,2-a]pyrazin-4-one)