NP-MRD: Showing NP-Card for (3s,7r,8as)-1,7-dihydroxy-3-(hydroxymethyl)-3h,6h,7h,8h,8ah-pyrrolo[1,2-a]pyrazin-4-one (NP0314744)

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Record Information

Version

2.0

Created at

2022-09-11 13:00:23 UTC

Updated at

2022-09-11 13:00:23 UTC

NP-MRD ID

NP0314744

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(3s,7r,8as)-1,7-dihydroxy-3-(hydroxymethyl)-3h,6h,7h,8h,8ah-pyrrolo[1,2-a]pyrazin-4-one

Description

JBP485, also known as JBP 485, belongs to the class of organic compounds known as alpha amino acids and derivatives. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon), or a derivative thereof. (3s,7r,8as)-1,7-dihydroxy-3-(hydroxymethyl)-3h,6h,7h,8h,8ah-pyrrolo[1,2-a]pyrazin-4-one is found in Aspergillus fumigatus. (3s,7r,8as)-1,7-dihydroxy-3-(hydroxymethyl)-3h,6h,7h,8h,8ah-pyrrolo[1,2-a]pyrazin-4-one was first documented in 2018 (PMID: 29964132). Based on a literature review a small amount of articles have been published on JBP485 (PMID: 35754503) (PMID: 34808388) (PMID: 31393124) (PMID: 30590313).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309112215002D          

 14 15  0  0  1  0            999 V2000
    3.2789    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    0.8250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.7079    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4223    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    0.0000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    0.0000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7798   -0.2549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2949    0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4699    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7798    1.0799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    0.8250    0.0000 N   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  1  6  0  0  0
  4  5  1  0  0  0  0
  3  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  1  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
  2 14  1  0  0  0  0
  9 14  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0314744

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC[C@@H]1N=C(O)[C@@H]2C[C@@H](O)CN2C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C8H12N2O4/c11-3-5-8(14)10-2-4(12)1-6(10)7(13)9-5/h4-6,11-12H,1-3H2,(H,9,13)/t4-,5+,6+/m1/s1

> <INCHI_KEY>
FUYZNZHRVJWTLT-SRQIZXRXSA-N

> <FORMULA>
C8H12N2O4

> <MOLECULAR_WEIGHT>
200.194

> <EXACT_MASS>
200.079706874

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
26

> <JCHEM_AVERAGE_POLARIZABILITY>
18.72887549046549

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(3S,7R,8aS)-1,7-dihydroxy-3-(hydroxymethyl)-3H,4H,6H,7H,8H,8aH-pyrrolo[1,2-a]pyrazin-4-one

> <JCHEM_LOGP>
-2.175375869666667

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.49696968344735

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.254082138959799

> <JCHEM_PKA_STRONGEST_BASIC>
0.21458657419011573

> <JCHEM_POLAR_SURFACE_AREA>
93.36

> <JCHEM_REFRACTIVITY>
45.6672

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(3S,7R,8aS)-1,7-dihydroxy-3-(hydroxymethyl)-3H,6H,7H,8H,8aH-pyrrolo[1,2-a]pyrazin-4-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 11-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-22         0                                  
HETATM    1  O   UNK     0       6.121   3.850   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       6.121   2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.454   1.540   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.788   2.310   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      10.122   1.540   0.000  0.00  0.00           O+0
HETATM    6  N   UNK     0       7.454   0.000   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0       6.121  -0.770   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       6.121  -2.310   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       4.787   0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.322  -0.476   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.417   0.770   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       0.877   0.770   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       3.322   2.016   0.000  0.00  0.00           C+0
HETATM   14  N   UNK     0       4.787   1.540   0.000  0.00  0.00           N+0
CONECT    1    2                                                            
CONECT    2    1    3   14                                                  
CONECT    3    2    4    6                                                  
CONECT    4    3    5                                                       
CONECT    5    4                                                            
CONECT    6    3    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   14                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13    2    9                                                  
MASTER        0    0    0    0    0    0    0    0   14    0   30    0
END

View in JSmol

Synonyms

Value	Source
JBP 485	MeSH
JBP-485	MeSH
Cyclo(4-hydroxyprolyl-seryl)	MeSH

Chemical Formula

C₈H₁₂N₂O₄

Average Mass

200.1940 Da

Monoisotopic Mass

200.07971 Da

IUPAC Name

(3S,7R,8aS)-1,7-dihydroxy-3-(hydroxymethyl)-3H,4H,6H,7H,8H,8aH-pyrrolo[1,2-a]pyrazin-4-one

Traditional Name

(3S,7R,8aS)-1,7-dihydroxy-3-(hydroxymethyl)-3H,6H,7H,8H,8aH-pyrrolo[1,2-a]pyrazin-4-one

CAS Registry Number

Not Available

SMILES

OC[C@@H]1N=C(O)[C@@H]2C[C@@H](O)CN2C1=O

InChI Identifier

InChI=1S/C8H12N2O4/c11-3-5-8(14)10-2-4(12)1-6(10)7(13)9-5/h4-6,11-12H,1-3H2,(H,9,13)/t4-,5+,6+/m1/s1

InChI Key

FUYZNZHRVJWTLT-SRQIZXRXSA-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
Aspergillus fumigatus	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as alpha amino acids and derivatives. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon), or a derivative thereof.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Alpha amino acids and derivatives

Alternative Parents

Substituents

Alpha-amino acid or derivatives
Dioxopiperazine
2,5-dioxopiperazine
N-alkylpiperazine
1,4-diazinane
Piperazine
Pyrrolidine
Tertiary carboxylic acid amide
Secondary carboxylic acid amide
Secondary alcohol
Lactam
Carboxamide group
Azacycle
Organoheterocyclic compound
Alcohol
Primary alcohol
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Organic oxide
Organic oxygen compound
Carbonyl group
Organic nitrogen compound
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic 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	-2.2	ChemAxon
pKa (Strongest Acidic)	4.25	ChemAxon
pKa (Strongest Basic)	0.21	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	93.36 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	45.67 m³·mol⁻¹	ChemAxon
Polarizability	18.73 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	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

7991337

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

9815587

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Wang C, Wang C, Wu J, Meng Q, Jin H, Sun H, Kaku T, Chen J, Huo X, Liu K: JBP485, A Dual Inhibitor of Organic Anion Transporters (OATs) and Renal Dehydropeptidase-I (DHP-I), Protects Against Imipenem-Induced Nephrotoxicity. Front Pharmacol. 2022 Jun 8;13:938813. doi: 10.3389/fphar.2022.938813. eCollection 2022. [PubMed:35754503 ]
Wu B, Zheng X, Li X, Wang C, Li L, Tang Z, Cui H, Li Z, Chen L, Ma X: Design, synthesis and activity evaluation of prodrug form JBP485 and Vitamin E for alleviation of NASH. Bioorg Med Chem Lett. 2022 Jan 15;56:128464. doi: 10.1016/j.bmcl.2021.128464. Epub 2021 Nov 19. [PubMed:34808388 ]
Jiang Q, Zhang J, Tong P, Gao Y, Lv Y, Wang C, Luo M, Sun M, Wang J, Feng Y, Cao L, Wang G, Wang Y, Kan Q, Zhang T, Wang Y, Liu K, Sun J, He Z: Bioactivatable Pseudotripeptidization of Cyclic Dipeptides To Increase the Affinity toward Oligopeptide Transporter 1 for Enhanced Oral Absorption: An Application to Cyclo(l-Hyp-l-Ser) (JBP485). J Med Chem. 2019 Sep 12;62(17):7708-7721. doi: 10.1021/acs.jmedchem.9b00358. Epub 2019 Sep 3. [PubMed:31393124 ]
Shu R, Wang C, Meng Q, Liu Z, Wu J, Sun P, Sun H, Ma X, Huo X, Liu K: Resveratrol enhances the protective effects of JBP485 against indomethacin-induced rat intestinal damage in vivo and vitro through up-regulating oligopeptide transporter 1 (Pept1). Biomed Pharmacother. 2019 Mar;111:251-261. doi: 10.1016/j.biopha.2018.12.084. Epub 2018 Dec 24. [PubMed:30590313 ]
Wen S, Wang C, Huo X, Meng Q, Liu Z, Yang S, Zhu Y, Sun H, Ma X, Liu K: JBP485 attenuates vancomycin-induced nephrotoxicity by regulating the expressions of organic anion transporter (Oat) 1, Oat3, organic cation transporter 2 (Oct2), multidrug resistance-associated protein 2 (Mrp2) and P-glycoprotein (P-gp) in rats. Toxicol Lett. 2018 Oct 1;295:195-204. doi: 10.1016/j.toxlet.2018.06.1220. Epub 2018 Jun 28. [PubMed:29964132 ]
LOTUS database [Link]

Showing NP-Card for (3s,7r,8as)-1,7-dihydroxy-3-(hydroxymethyl)-3h,6h,7h,8h,8ah-pyrrolo[1,2-a]pyrazin-4-one (NP0314744)

MOL for NP0314744 ((3s,7r,8as)-1,7-dihydroxy-3-(hydroxymethyl)-3h,6h,7h,8h,8ah-pyrrolo[1,2-a]pyrazin-4-one)

3D MOL for NP0314744 ((3s,7r,8as)-1,7-dihydroxy-3-(hydroxymethyl)-3h,6h,7h,8h,8ah-pyrrolo[1,2-a]pyrazin-4-one)

3D SDF for NP0314744 ((3s,7r,8as)-1,7-dihydroxy-3-(hydroxymethyl)-3h,6h,7h,8h,8ah-pyrrolo[1,2-a]pyrazin-4-one)

3D-SDF for NP0314744 ((3s,7r,8as)-1,7-dihydroxy-3-(hydroxymethyl)-3h,6h,7h,8h,8ah-pyrrolo[1,2-a]pyrazin-4-one)

PDB for NP0314744 ((3s,7r,8as)-1,7-dihydroxy-3-(hydroxymethyl)-3h,6h,7h,8h,8ah-pyrrolo[1,2-a]pyrazin-4-one)

3D PDB for NP0314744 ((3s,7r,8as)-1,7-dihydroxy-3-(hydroxymethyl)-3h,6h,7h,8h,8ah-pyrrolo[1,2-a]pyrazin-4-one)

SMILES for NP0314744 ((3s,7r,8as)-1,7-dihydroxy-3-(hydroxymethyl)-3h,6h,7h,8h,8ah-pyrrolo[1,2-a]pyrazin-4-one)

INCHI for NP0314744 ((3s,7r,8as)-1,7-dihydroxy-3-(hydroxymethyl)-3h,6h,7h,8h,8ah-pyrrolo[1,2-a]pyrazin-4-one)

Structure for NP0314744 ((3s,7r,8as)-1,7-dihydroxy-3-(hydroxymethyl)-3h,6h,7h,8h,8ah-pyrrolo[1,2-a]pyrazin-4-one)

3D Structure for NP0314744 ((3s,7r,8as)-1,7-dihydroxy-3-(hydroxymethyl)-3h,6h,7h,8h,8ah-pyrrolo[1,2-a]pyrazin-4-one)