NP-MRD: Showing NP-Card for F-14329 (NP0331288)

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Record Information

Version

1.0

Created at

2022-12-22 08:49:38 UTC

Updated at

2024-04-19 09:35:37 UTC

NP-MRD ID

NP0331288

Secondary Accession Numbers

None

Natural Product Identification

Common Name

F-14329

Description

(3Z,5S)-3-[(2S,4S,6E)-1-hydroxy-2,4-dimethyl-6-octen-1-ylidene]-5-[(S)-hydroxy(4-hydroxyphenyl)methyl]-2,4-pyrrolidinedione belongs to the class of organic compounds known as 1-hydroxy-2-unsubstituted benzenoids. These are phenols that are unsubstituted at the 2-position. It was first documented in 2023 (PMID: 37078450). Based on a literature review a significant number of articles have been published on (3Z,5S)-3-[(2S,4S,6E)-1-hydroxy-2,4-dimethyl-6-octen-1-ylidene]-5-[(S)-hydroxy(4-hydroxyphenyl)methyl]-2,4-pyrrolidinedione (PMID: 37078444) (PMID: 37078443) (PMID: 37078154) (PMID: 37078114).

Structure

MOL SDF PDB SMILES InChI


  Mrv1652312222209492D          

 27 28  0  0  1  0            999 V2000
   -2.6960   -3.0318    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3090   -3.5838    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2228   -4.4043    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5083   -4.8168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5083   -5.6418    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7939   -4.4043    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.7939   -3.5793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0794   -4.8168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3649   -4.4043    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3649   -3.5793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3495   -4.8168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0640   -4.4043    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7785   -4.8168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4930   -4.4043    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1160   -3.4123    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.4516   -2.6586    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.9667   -1.9912    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2721   -2.5724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7570   -3.2398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5775   -3.1536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9130   -2.3999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7335   -2.3137    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4281   -1.7325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6076   -1.8187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5285   -4.1268    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9765   -4.7399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1480   -5.5468    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  4  6  1  0  0  0  0
  6  7  1  1  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  1  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
  2 15  1  0  0  0  0
 15 16  1  1  0  0  0
 16 17  1  6  0  0  0
 16 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
 23 24  2  0  0  0  0
 18 24  1  0  0  0  0
 15 25  1  0  0  0  0
 25 26  1  0  0  0  0
  3 26  1  0  0  0  0
 26 27  2  0  0  0  0
M  END


  Mrv1652312222209492D          

 27 28  0  0  1  0            999 V2000
   -2.6960   -3.0318    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3090   -3.5838    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2228   -4.4043    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5083   -4.8168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5083   -5.6418    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7939   -4.4043    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.7939   -3.5793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0794   -4.8168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3649   -4.4043    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3649   -3.5793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3495   -4.8168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0640   -4.4043    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7785   -4.8168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4930   -4.4043    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1160   -3.4123    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.4516   -2.6586    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.9667   -1.9912    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2721   -2.5724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7570   -3.2398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5775   -3.1536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9130   -2.3999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7335   -2.3137    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4281   -1.7325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6076   -1.8187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5285   -4.1268    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9765   -4.7399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1480   -5.5468    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  4  6  1  0  0  0  0
  6  7  1  1  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  1  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
  2 15  1  0  0  0  0
 15 16  1  1  0  0  0
 16 17  1  6  0  0  0
 16 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
 23 24  2  0  0  0  0
 18 24  1  0  0  0  0
 15 25  1  0  0  0  0
 25 26  1  0  0  0  0
  3 26  1  0  0  0  0
 26 27  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0331288

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C\C=C\C[C@H](C)C[C@H](C)C(\O)=C1\C(=O)N[C@@H]([C@@H](O)C2=CC=C(O)C=C2)C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C21H27NO5/c1-4-5-6-12(2)11-13(3)18(24)16-20(26)17(22-21(16)27)19(25)14-7-9-15(23)10-8-14/h4-5,7-10,12-13,17,19,23-25H,6,11H2,1-3H3,(H,22,27)/b5-4+,18-16-/t12-,13-,17-,19-/m0/s1

> <INCHI_KEY>
IWIISBMWNKBQQH-WZFGYRRTSA-N

> <FORMULA>
C21H27NO5

> <MOLECULAR_WEIGHT>
373.449

> <EXACT_MASS>
373.188922973

$$$$

HEADER    PROTEIN                                 22-DEC-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   22-DEC-22         0                                  
HETATM    1  O   UNK     0      -5.032  -5.659   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      -6.177  -6.690   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -6.016  -8.221   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -4.682  -8.991   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      -4.682 -10.531   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      -3.349  -8.221   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -3.349  -6.681   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.015  -8.991   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.681  -8.221   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.681  -6.681   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.652  -8.991   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.986  -8.221   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.320  -8.991   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.654  -8.221   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -7.683  -6.370   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -8.310  -4.963   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -7.404  -3.717   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      -9.841  -4.802   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0     -10.746  -6.048   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0     -12.278  -5.887   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0     -12.904  -4.480   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0     -14.436  -4.319   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0     -11.999  -3.234   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0     -10.468  -3.395   0.000  0.00  0.00           C+0
HETATM   25  N   UNK     0      -8.453  -7.703   0.000  0.00  0.00           N+0
HETATM   26  C   UNK     0      -7.423  -8.848   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      -7.743 -10.354   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   15                                                  
CONECT    3    2    4   26                                                  
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13                                                            
CONECT   15    2   16   25                                                  
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19   24                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24                                                       
CONECT   24   23   18                                                       
CONECT   25   15   26                                                       
CONECT   26   25    3   27                                                  
CONECT   27   26                                                            
MASTER        0    0    0    0    0    0    0    0   27    0   56    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₁H₂₇NO₅

Average Mass

373.4490 Da

Monoisotopic Mass

373.18892 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

C\C=C\C[C@H](C)C[C@H](C)C(\O)=C1\C(=O)N[C@@H]([C@@H](O)C2=CC=C(O)C=C2)C1=O

InChI Identifier

InChI=1S/C21H27NO5/c1-4-5-6-12(2)11-13(3)18(24)16-20(26)17(22-21(16)27)19(25)14-7-9-15(23)10-8-14/h4-5,7-10,12-13,17,19,23-25H,6,11H2,1-3H3,(H,22,27)/b5-4+,18-16-/t12-,13-,17-,19-/m0/s1

InChI Key

IWIISBMWNKBQQH-WZFGYRRTSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
ROESY NMR	[¹H, ¹H] NMR Spectrum (2D, 600 MHz, C2D6OS, experimental)	r.capon@imb.uq.edu.au	Not Available	Not Available	2022-12-22	View Spectrum
HMBC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, C2D6OS, experimental)	r.capon@imb.uq.edu.au	Not Available	Not Available	2022-12-22	View Spectrum
HSQC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, C2D6OS, experimental)	r.capon@imb.uq.edu.au	Not Available	Not Available	2022-12-22	View Spectrum
COSY NMR	[¹H, ¹H] NMR Spectrum (2D, 600 MHz, C2D6OS, experimental)	r.capon@imb.uq.edu.au	Not Available	Not Available	2022-12-22	View Spectrum
1D NMR	[¹³C, ] NMR Spectrum (2D, 151 MHz, C2D6OS, experimental)	r.capon@imb.uq.edu.au	Not Available	Not Available	2022-12-22	View Spectrum
ROESY NMR	[¹H, ¹H] NMR Spectrum (2D, 600 MHz, CDCl3, experimental)	r.capon@imb.uq.edu.au	Not Available	Not Available	2022-12-22	View Spectrum
1D NMR	[¹H, ] NMR Spectrum (2D, 600 MHz, C2D6OS, experimental)	r.capon@imb.uq.edu.au	Not Available	Not Available	2022-12-22	View Spectrum
HMBC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, CDCl3, experimental)	r.capon@imb.uq.edu.au	Not Available	Not Available	2022-12-22	View Spectrum
HSQC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, CDCl3, experimental)	r.capon@imb.uq.edu.au	Not Available	Not Available	2022-12-22	View Spectrum
COSY NMR	[¹H, ¹H] NMR Spectrum (2D, 600 MHz, CDCl3, experimental)	r.capon@imb.uq.edu.au	Not Available	Not Available	2022-12-22	View Spectrum
1D NMR	[¹³C, ] NMR Spectrum (2D, 151 MHz, CDCl3, experimental)	r.capon@imb.uq.edu.au	Not Available	Not Available	2022-12-22	View Spectrum
1D NMR	[¹H, ] NMR Spectrum (2D, 600 MHz, CDCl3, experimental)	r.capon@imb.uq.edu.au	Not Available	Not Available	2022-12-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600.08 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 150.91 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600.08 MHz, C2D6OS, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 150.91 MHz, C2D6OS, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 1-hydroxy-2-unsubstituted benzenoids. These are phenols that are unsubstituted at the 2-position.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Phenols

Sub Class

1-hydroxy-2-unsubstituted benzenoids

Direct Parent

1-hydroxy-2-unsubstituted benzenoids

Alternative Parents

Substituents

1-hydroxy-2-unsubstituted benzenoid
3-pyrrolidone
2-pyrrolidone
Pyrrolidone
Monocyclic benzene moiety
Vinylogous acid
Pyrrolidine
Cyclic ketone
Secondary carboxylic acid amide
Secondary alcohol
Lactam
Ketone
Carboxamide group
Azacycle
Organoheterocyclic compound
Enol
Carboxylic acid derivative
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Aromatic alcohol
Organooxygen compound
Organonitrogen compound
Carbonyl group
Alcohol
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic 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

35517105

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

156588973

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Russi AE, Shivakumar P, Luo Z, Bezerra J: Plasticity between ILC2 subsets and amphiregulin expression regulate epithelial repair in biliary atresia. Hepatology. 2023 Apr 21. doi: 10.1097/HEP.0000000000000418. [PubMed:37078450 ]
Hlady RA, Robertson KD: Epigenetic memory of environmental exposures as a mediator of liver disease. Hepatology. 2023 Apr 21. doi: 10.1097/HEP.0000000000000414. [PubMed:37078444 ]
Ufere NN: Home is where the liver is?: moving beyond readmissions to time at home as a patient-centered and pragmatic quality measure in cirrhosis care. Hepatology. 2023 Apr 21. doi: 10.1097/HEP.0000000000000415. [PubMed:37078443 ]
Arnon R, Rubinov A: [[PTOSIS AS A SIGN OF A SYSTEMIC DISEASE]]. Harefuah. 2023 Feb;162(2):119-121. [PubMed:37078154 ]
Shemesh N, Olshaker H: [[A MULTICENTER SPANISH STUDY OF ATROPINE 0.01% IN CHILDHOOD MYOPIA PROGRESSION]]. Harefuah. 2023 Feb;162(2):116-118. [PubMed:37078114 ]

Showing NP-Card for F-14329 (NP0331288)

MOL for NP0331288 (F-14329)

3D MOL for NP0331288 (F-14329)

3D SDF for NP0331288 (F-14329)

3D-SDF for NP0331288 (F-14329)

PDB for NP0331288 (F-14329)

3D PDB for NP0331288 (F-14329)

SMILES for NP0331288 (F-14329)

INCHI for NP0331288 (F-14329)

Structure for NP0331288 (F-14329)

3D Structure for NP0331288 (F-14329)