NP-MRD: Showing NP-Card for (2r)-2-[(1s)-1-hydroxy-3-methylbutyl]-6-methyl-2h-[1,3]dioxolo[4,5-c]pyridin-4-ol (NP0157605)

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Record Information

Version

2.0

Created at

2022-09-02 15:01:32 UTC

Updated at

2022-09-02 15:01:33 UTC

NP-MRD ID

NP0157605

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2r)-2-[(1s)-1-hydroxy-3-methylbutyl]-6-methyl-2h-[1,3]dioxolo[4,5-c]pyridin-4-ol

Description

Dihydroisoflavipucine belongs to the class of organic compounds known as pyridinones. Pyridinones are compounds containing a pyridine ring, which bears a ketone. (2r)-2-[(1s)-1-hydroxy-3-methylbutyl]-6-methyl-2h-[1,3]dioxolo[4,5-c]pyridin-4-ol was first documented in 2011 (PMID: 21236704). Based on a literature review a small amount of articles have been published on Dihydroisoflavipucine (PMID: 34459930) (PMID: 34554766) (PMID: 26603760).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 34 35  0  0  0  0  0  0  0  0999 V2000
    5.8583    0.8925   -0.0031 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5322    0.2136   -0.1052 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3543    0.8567    0.2177 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1216    0.2392    0.1273 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0943   -1.0697   -0.3047 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2688   -1.7052   -0.6248 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2489   -3.0222   -1.0601 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4716   -1.0638   -0.5236 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7817   -1.5109   -0.3291 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0358   -0.5544    0.3627 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.2828   -0.3935   -0.4365 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.9964   -1.6106   -0.3292 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2022    0.6706    0.1251 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4919    0.7656   -0.6274 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2890   -0.5011   -0.6195 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3376    1.8842   -0.0579 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7957    0.5752    0.3621 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8456    1.7171    0.7381 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6407    0.1800    0.3405 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1782    1.2907   -0.9659 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3774    1.8662    0.5507 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8476   -3.7588   -0.4836 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2025   -0.9766    1.3657 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0247   -0.1630   -1.4828 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8771   -1.9718    0.5912 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4306    0.4590    1.1876 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7286    1.6763    0.1042 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2334    1.0160   -1.6890 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3946   -0.2877   -0.7037 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9985   -1.1727   -1.4540 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1818   -1.0827    0.3144 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6137    2.6229   -0.8291 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8094    2.4295    0.7492 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2861    1.4890    0.3847 H   0  0  0  0  0  0  0  0  0  0  0  0
 15 14  1  0
 14 16  1  0
 14 13  1  0
 13 11  1  0
 11 12  1  0
 11 10  1  0
 10 17  1  0
 17  4  1  0
  4  5  2  0
  5  9  1  0
  5  6  1  0
  6  7  1  0
  6  8  2  0
  8  2  1  0
  2  1  1  0
  2  3  2  0
  9 10  1  0
  3  4  1  0
 15 29  1  0
 15 30  1  0
 15 31  1  0
 14 28  1  0
 16 32  1  0
 16 33  1  0
 16 34  1  0
 13 26  1  0
 13 27  1  0
 11 24  1  6
 12 25  1  0
 10 23  1  1
  7 22  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  3 21  1  0
M  END


  Mrv1652309022217012D          

 17 18  0  0  1  0            999 V2000
    2.7845    0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556    0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556    3.1729    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701    1.9354    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435    2.1904    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6284    1.5229    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4534    1.5229    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.8659    2.2374    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8659    0.8085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6909    0.8085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1034    0.0940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1034    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435    0.8555    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  2  0  0  0  0
  2  8  1  0  0  0  0
  5  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  1  0  0  0
 11 12  1  6  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
 10 17  1  0  0  0  0
  4 17  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0157605

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)C[C@H](O)[C@@H]1OC2=C(O1)C(O)=NC(C)=C2

> <INCHI_IDENTIFIER>
InChI=1S/C12H17NO4/c1-6(2)4-8(14)12-16-9-5-7(3)13-11(15)10(9)17-12/h5-6,8,12,14H,4H2,1-3H3,(H,13,15)/t8-,12+/m0/s1

> <INCHI_KEY>
OWGDONWQBHBJKL-QPUJVOFHSA-N

> <FORMULA>
C12H17NO4

> <MOLECULAR_WEIGHT>
239.271

> <EXACT_MASS>
239.115758031

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
34

> <JCHEM_AVERAGE_POLARIZABILITY>
25.623193518406254

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2R)-2-[(1S)-1-hydroxy-3-methylbutyl]-6-methyl-2H-[1,3]dioxolo[4,5-c]pyridin-4-ol

> <ALOGPS_LOGP>
1.78

> <JCHEM_LOGP>
1.9974295309999999

> <ALOGPS_LOGS>
-1.29

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.393909631500385

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.828903807772035

> <JCHEM_PKA_STRONGEST_BASIC>
1.418153817442439

> <JCHEM_POLAR_SURFACE_AREA>
71.81000000000002

> <JCHEM_REFRACTIVITY>
60.86670000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.23e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2R)-2-[(1S)-1-hydroxy-3-methylbutyl]-6-methyl-2H-[1,3]dioxolo[4,5-c]pyridin-4-ol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 02-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-SEP-22         0                                  
HETATM    1  C   UNK     0       5.198   1.303   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.864   2.073   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.530   1.303   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.197   2.073   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.197   3.613   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.530   4.383   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       2.530   5.923   0.000  0.00  0.00           O+0
HETATM    8  N   UNK     0       3.864   3.613   0.000  0.00  0.00           N+0
HETATM    9  O   UNK     0      -0.268   4.089   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      -1.173   2.843   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -2.713   2.843   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -3.483   4.177   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      -3.483   1.509   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -5.023   1.509   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -5.793   0.175   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -5.793   2.843   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -0.268   1.597   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    8                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   17                                                  
CONECT    5    4    6    9                                                  
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    2                                                       
CONECT    9    5   10                                                       
CONECT   10    9   11   17                                                  
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14                                                            
CONECT   17   10    4                                                       
MASTER        0    0    0    0    0    0    0    0   17    0   36    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₂H₁₇NO₄

Average Mass

239.2710 Da

Monoisotopic Mass

239.11576 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

CC(C)C[C@H](O)[C@@H]1OC2=C(O1)C(O)=NC(C)=C2

InChI Identifier

InChI=1S/C12H17NO4/c1-6(2)4-8(14)12-16-9-5-7(3)13-11(15)10(9)17-12/h5-6,8,12,14H,4H2,1-3H3,(H,13,15)/t8-,12+/m0/s1

InChI Key

OWGDONWQBHBJKL-QPUJVOFHSA-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 pyridinones. Pyridinones are compounds containing a pyridine ring, which bears a ketone.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Pyridines and derivatives

Sub Class

Hydropyridines

Direct Parent

Pyridinones

Alternative Parents

Substituents

Pyridinone
Methylpyridine
Vinylogous ester
Heteroaromatic compound
Lactam
Secondary alcohol
Acetal
Azacycle
Oxacycle
Organic oxide
Organopnictogen compound
Organic oxygen compound
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Alcohol
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

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

78437069

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

38354263

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Du X, Li H, Qi J, Chen C, Lu Y, Wang Y: Genome mining of secondary metabolites from a marine-derived Aspergillus terreus B12. Arch Microbiol. 2021 Nov;203(9):5621-5633. doi: 10.1007/s00203-021-02548-4. Epub 2021 Aug 30. [PubMed:34459930 ]
Wei G, Shu X, Yao Y, Zhang K, Zhang J, Gao SS: Heterologous Production of Unnatural Flavipucine Family Products Provides Insights into Flavipucines Biosynthesis. Org Lett. 2021 Oct 15;23(20):7708-7712. doi: 10.1021/acs.orglett.1c02566. Epub 2021 Sep 23. [PubMed:34554766 ]
Boruta T, Bizukojc M: Induction of secondary metabolism of Aspergillus terreus ATCC 20542 in the batch bioreactor cultures. Appl Microbiol Biotechnol. 2016 Apr;100(7):3009-22. doi: 10.1007/s00253-015-7157-1. Epub 2015 Nov 25. [PubMed:26603760 ]
Gressler M, Zaehle C, Scherlach K, Hertweck C, Brock M: Multifactorial induction of an orphan PKS-NRPS gene cluster in Aspergillus terreus. Chem Biol. 2011 Feb 25;18(2):198-209. doi: 10.1016/j.chembiol.2010.12.011. Epub 2011 Jan 13. [PubMed:21236704 ]
LOTUS database [Link]

Showing NP-Card for (2r)-2-[(1s)-1-hydroxy-3-methylbutyl]-6-methyl-2h-[1,3]dioxolo[4,5-c]pyridin-4-ol (NP0157605)

MOL for NP0157605 ((2r)-2-[(1s)-1-hydroxy-3-methylbutyl]-6-methyl-2h-[1,3]dioxolo[4,5-c]pyridin-4-ol)

3D MOL for NP0157605 ((2r)-2-[(1s)-1-hydroxy-3-methylbutyl]-6-methyl-2h-[1,3]dioxolo[4,5-c]pyridin-4-ol)

3D SDF for NP0157605 ((2r)-2-[(1s)-1-hydroxy-3-methylbutyl]-6-methyl-2h-[1,3]dioxolo[4,5-c]pyridin-4-ol)

3D-SDF for NP0157605 ((2r)-2-[(1s)-1-hydroxy-3-methylbutyl]-6-methyl-2h-[1,3]dioxolo[4,5-c]pyridin-4-ol)

PDB for NP0157605 ((2r)-2-[(1s)-1-hydroxy-3-methylbutyl]-6-methyl-2h-[1,3]dioxolo[4,5-c]pyridin-4-ol)

3D PDB for NP0157605 ((2r)-2-[(1s)-1-hydroxy-3-methylbutyl]-6-methyl-2h-[1,3]dioxolo[4,5-c]pyridin-4-ol)

SMILES for NP0157605 ((2r)-2-[(1s)-1-hydroxy-3-methylbutyl]-6-methyl-2h-[1,3]dioxolo[4,5-c]pyridin-4-ol)

INCHI for NP0157605 ((2r)-2-[(1s)-1-hydroxy-3-methylbutyl]-6-methyl-2h-[1,3]dioxolo[4,5-c]pyridin-4-ol)

Structure for NP0157605 ((2r)-2-[(1s)-1-hydroxy-3-methylbutyl]-6-methyl-2h-[1,3]dioxolo[4,5-c]pyridin-4-ol)

3D Structure for NP0157605 ((2r)-2-[(1s)-1-hydroxy-3-methylbutyl]-6-methyl-2h-[1,3]dioxolo[4,5-c]pyridin-4-ol)