NP-MRD: Showing NP-Card for (3r,5r)-3,5-dihydroxy-1-(3-methyl-2,5-dihydrofuran-2-yl)pyrrolidin-2-one (NP0251934)

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Record Information

Version

1.0

Created at

2022-09-07 15:17:03 UTC

Updated at

2022-09-07 15:17:03 UTC

NP-MRD ID

NP0251934

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(3r,5r)-3,5-dihydroxy-1-(3-methyl-2,5-dihydrofuran-2-yl)pyrrolidin-2-one

Description

Fulvanine B belongs to the class of organic compounds known as n-alkylpyrrolidines. N-alkylpyrrolidines are compounds containing a pyrrolidine moiety that is substituted at the N1-position with an alkyl group. Pyrrolidine is a five-membered saturated aliphatic heterocycle with one nitrogen atom and four carbon atoms. (3r,5r)-3,5-dihydroxy-1-(3-methyl-2,5-dihydrofuran-2-yl)pyrrolidin-2-one is found in Hemerocallis fulva. It was first documented in 2002 (PMID: 26389337). Based on a literature review a significant number of articles have been published on Fulvanine B (PMID: 36100310) (PMID: 36100309) (PMID: 36100308) (PMID: 36100300) (PMID: 36100248) (PMID: 36099751).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309072217172D          

 14 15  0  0  1  0            999 V2000
    1.2564   -0.1802    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2564   -1.0052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9239   -1.4901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6689   -2.2748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8439   -2.2748    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5890   -1.4901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1956   -1.2352    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8631   -1.7201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8631   -2.5451    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5305   -1.2352    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3151   -1.4901    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2756   -0.4506    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4506   -0.4506    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0343    0.2169    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  1  0  0  0  0
  5  6  1  0  0  0  0
  2  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  6  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
  7 13  1  0  0  0  0
 13 14  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0251934

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1=CCOC1N1[C@H](O)C[C@@H](O)C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C9H13NO4/c1-5-2-3-14-9(5)10-7(12)4-6(11)8(10)13/h2,6-7,9,11-12H,3-4H2,1H3/t6-,7-,9?/m1/s1

> <INCHI_KEY>
DEFSJMDKJOFVBS-UMPGHQJDSA-N

> <FORMULA>
C9H13NO4

> <MOLECULAR_WEIGHT>
199.206

> <EXACT_MASS>
199.084457903

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
27

> <JCHEM_AVERAGE_POLARIZABILITY>
19.313857468220544

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(3R,5R)-3,5-dihydroxy-1-(3-methyl-2,5-dihydrofuran-2-yl)pyrrolidin-2-one

> <JCHEM_LOGP>
-0.575719155333333

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.615463770529232

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.851453418491523

> <JCHEM_PKA_STRONGEST_BASIC>
-3.5244699817018885

> <JCHEM_POLAR_SURFACE_AREA>
70.0

> <JCHEM_REFRACTIVITY>
47.6322

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(3R,5R)-3,5-dihydroxy-1-(3-methyl-2,5-dihydrofuran-2-yl)pyrrolidin-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 07-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-SEP-22         0                                  
HETATM    1  C   UNK     0       2.345  -0.336   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.345  -1.876   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.591  -2.782   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.115  -4.246   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       1.575  -4.246   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       1.099  -2.782   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0      -0.365  -2.306   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0      -1.611  -3.211   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -1.611  -4.751   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      -2.857  -2.306   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -4.322  -2.782   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      -2.381  -0.841   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.841  -0.841   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       0.064   0.405   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    6                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    2    7                                                  
CONECT    7    6    8   13                                                  
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12    7   14                                                  
CONECT   14   13                                                            
MASTER        0    0    0    0    0    0    0    0   14    0   30    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₉H₁₃NO₄

Average Mass

199.2060 Da

Monoisotopic Mass

199.08446 Da

IUPAC Name

(3R,5R)-3,5-dihydroxy-1-(3-methyl-2,5-dihydrofuran-2-yl)pyrrolidin-2-one

Traditional Name

(3R,5R)-3,5-dihydroxy-1-(3-methyl-2,5-dihydrofuran-2-yl)pyrrolidin-2-one

CAS Registry Number

Not Available

SMILES

CC1=CCOC1N1[C@H](O)C[C@@H](O)C1=O

InChI Identifier

InChI=1S/C9H13NO4/c1-5-2-3-14-9(5)10-7(12)4-6(11)8(10)13/h2,6-7,9,11-12H,3-4H2,1H3/t6-,7-,9?/m1/s1

InChI Key

DEFSJMDKJOFVBS-UMPGHQJDSA-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
Hemerocallis fulva	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as n-alkylpyrrolidines. N-alkylpyrrolidines are compounds containing a pyrrolidine moiety that is substituted at the N1-position with an alkyl group. Pyrrolidine is a five-membered saturated aliphatic heterocycle with one nitrogen atom and four carbon atoms.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Pyrrolidines

Sub Class

N-alkylpyrrolidines

Direct Parent

N-alkylpyrrolidines

Alternative Parents

Substituents

N-alkylpyrrolidine
2-pyrrolidone
Pyrrolidone
Tertiary carboxylic acid amide
Dihydrofuran
Secondary alcohol
Lactam
Carboxamide group
Oxacycle
Azacycle
Carboxylic acid derivative
Alkanolamine
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Carbonyl group
Alcohol
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic 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
logP	-0.58	ChemAxon
pKa (Strongest Acidic)	12.85	ChemAxon
pKa (Strongest Basic)	-3.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	70 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	47.63 m³·mol⁻¹	ChemAxon
Polarizability	19.31 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

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

14779025

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

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Vavolizza RD, Petroni GR, Mauldin IS, Chianese-Bullock KA, Olson WC, Smith KT, Dengel LT, Haden K, Grosh WW, Kaur V, Varhegyi N, Gaughan EM, Slingluff CL Jr: Phase I/II clinical trial of a helper peptide vaccine plus PD-1 blockade in PD-1 antibody-naive and PD-1 antibody-experienced patients with melanoma (MEL64). J Immunother Cancer. 2022 Sep;10(9). pii: jitc-2022-005424. doi: 10.1136/jitc-2022-005424. [PubMed:36100309 ]
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Cibula D, Borcinova M, Kocian R, Feltl D, Argalacsova S, Dvorak P, Fischerova D, Dundr P, Jarkovsky J, Hoschlova E, Slama J, Scambia G: CERVANTES: an international randomized trial of radical surgery followed by adjuvant (chemo) radiation versus no further treatment in patients with early-stage, intermediate-risk cervical cancer (CEEGOG-CX-05; ENGOT-CX16). Int J Gynecol Cancer. 2022 Sep 13:ijgc-2022-003918. doi: 10.1136/ijgc-2022-003918. [PubMed:36100282 ]
Zhong X, Chen Z, Wang Y, Mao M, Deng Y, Shi M, Xu Y, Chen L, Cao W: JQ1 attenuates neuroinflammation by inhibiting the inflammasome-dependent canonical pyroptosis pathway in SAE. Brain Res Bull. 2022 Oct 15;189:174-183. doi: 10.1016/j.brainresbull.2022.09.007. Epub 2022 Sep 12. [PubMed:36100190 ]
Soneda K, Uda K, Araki K, Murakoshi T, Yuza Y, Saito O, Kinoshita K, Higuchi H, Horikoshi Y: Clinical characteristics and treatment of IMP-type carbapenemase-producing Enterobacteriaceae bacteremia: Case series and literature review. J Infect Chemother. 2023 Jan;29(1):26-32. doi: 10.1016/j.jiac.2022.09.003. Epub 2022 Sep 12. [PubMed:36100144 ]
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Mirlekar B, Wang Y, Li S, Zhou M, Entwistle S, De Buysscher T, Morrison A, Herrera G, Harris C, Vincent BG, Ting JP, Rashid N, Kim WY, Yeh JJ, Pylayeva-Gupta Y: Balance between immunoregulatory B cells and plasma cells drives pancreatic tumor immunity. Cell Rep Med. 2022 Sep 20;3(9):100744. doi: 10.1016/j.xcrm.2022.100744. Epub 2022 Sep 12. [PubMed:36099917 ]
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LOTUS database [Link]

Showing NP-Card for (3r,5r)-3,5-dihydroxy-1-(3-methyl-2,5-dihydrofuran-2-yl)pyrrolidin-2-one (NP0251934)

MOL for NP0251934 ((3r,5r)-3,5-dihydroxy-1-(3-methyl-2,5-dihydrofuran-2-yl)pyrrolidin-2-one)

3D MOL for NP0251934 ((3r,5r)-3,5-dihydroxy-1-(3-methyl-2,5-dihydrofuran-2-yl)pyrrolidin-2-one)

3D SDF for NP0251934 ((3r,5r)-3,5-dihydroxy-1-(3-methyl-2,5-dihydrofuran-2-yl)pyrrolidin-2-one)

3D-SDF for NP0251934 ((3r,5r)-3,5-dihydroxy-1-(3-methyl-2,5-dihydrofuran-2-yl)pyrrolidin-2-one)

PDB for NP0251934 ((3r,5r)-3,5-dihydroxy-1-(3-methyl-2,5-dihydrofuran-2-yl)pyrrolidin-2-one)

3D PDB for NP0251934 ((3r,5r)-3,5-dihydroxy-1-(3-methyl-2,5-dihydrofuran-2-yl)pyrrolidin-2-one)

SMILES for NP0251934 ((3r,5r)-3,5-dihydroxy-1-(3-methyl-2,5-dihydrofuran-2-yl)pyrrolidin-2-one)

INCHI for NP0251934 ((3r,5r)-3,5-dihydroxy-1-(3-methyl-2,5-dihydrofuran-2-yl)pyrrolidin-2-one)

Structure for NP0251934 ((3r,5r)-3,5-dihydroxy-1-(3-methyl-2,5-dihydrofuran-2-yl)pyrrolidin-2-one)

3D Structure for NP0251934 ((3r,5r)-3,5-dihydroxy-1-(3-methyl-2,5-dihydrofuran-2-yl)pyrrolidin-2-one)