NP-MRD: Showing NP-Card for Lentofuranine (NP0350826)

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Record Information

Version

2.0

Created at

2025-03-12 00:54:57 UTC

Updated at

2025-03-13 00:06:26 UTC

NP-MRD ID

NP0350826

Natural Product DOI

https://doi.org/10.57994/3811

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Lentofuranine

Description

Lentofuranine was first documented in 2023 (PMID: 36706030). Based on a literature review very few articles have been published on Lentofuranine (PMID: 38517623).

Structure

MOL SDF PDB SMILES InChI


  Mrv2104 06092301012D          

 22 23  0  0  0  0            999 V2000
   -3.0907    4.5517    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2657    4.5517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8532    5.2661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2657    5.9806    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0282    5.2661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6157    4.5517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1913    4.3801    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2775    3.5596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9920    3.1471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7065    3.5596    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4209    3.1471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4209    2.3221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1354    3.5596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8499    3.1471    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1354    4.3846    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9920    2.3221    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4761    3.2241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0282    3.8372    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8532    3.8372    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2657    3.1227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0907    3.1227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5032    2.4082    0.0000 C   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
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  2  0  0  0  0
  9 16  2  0  0  0  0
  8 17  2  0  0  0  0
  6 18  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
  2 19  1  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
M  END
> <DATABASE_ID>
NP0350826

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C\C=C\C1=C2C=C(OC2=CC(O)=C1O)C(=O)NC(C)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1/C15H15NO6/c1-3-4-8-9-5-12(14(19)16-7(2)15(20)21)22-11(9)6-10(17)13(8)18/h3-7,17-18H,1-2H3,(H,16,19)(H,20,21)/b4-3+

> <INCHI_KEY>
GUHJREMXNVVWRT-ONEGZZNKNA-N

> <FORMULA>
C15H15NO6

> <MOLECULAR_WEIGHT>
305.286

> <EXACT_MASS>
305.089937207

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
37

> <JCHEM_AVERAGE_POLARIZABILITY>
30.884973081500235

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-({5,6-dihydroxy-4-[(1E)-prop-1-en-1-yl]-1-benzofuran-2-yl}formamido)propanoic acid

> <JCHEM_LOGP>
1.6896406703333329

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
8.231812113525766

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.5336524519900014

> <JCHEM_PKA_STRONGEST_BASIC>
-2.906194541582458

> <JCHEM_POLAR_SURFACE_AREA>
120.0

> <JCHEM_REFRACTIVITY>
78.65180000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
2-({5,6-dihydroxy-4-[(1E)-prop-1-en-1-yl]-1-benzofuran-2-yl}formamido)propanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 09-JUN-23   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   09-JUN-23         0                                  
HETATM    1  O   UNK     0      -5.769   8.496   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      -4.229   8.496   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -3.459   9.830   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      -4.229  11.164   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      -1.919   9.830   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.149   8.496   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       0.357   8.176   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       0.518   6.645   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.852   5.875   0.000  0.00  0.00           C+0
HETATM   10  N   UNK     0       3.185   6.645   0.000  0.00  0.00           N+0
HETATM   11  C   UNK     0       4.519   5.875   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.519   4.335   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.853   6.645   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       7.186   5.875   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0       5.853   8.185   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       1.852   4.335   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      -0.889   6.018   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -1.919   7.163   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -3.459   7.163   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -4.229   5.829   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -5.769   5.829   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -6.539   4.495   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   19                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7   18                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   17                                                  
CONECT    9    8   10   16                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13                                                            
CONECT   16    9                                                            
CONECT   17    8   18                                                       
CONECT   18    6   17   19                                                  
CONECT   19   18    2   20                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   46    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₅H₁₅NO₆

Average Mass

305.2860 Da

Monoisotopic Mass

305.08994 Da

IUPAC Name

2-({5,6-dihydroxy-4-[(1E)-prop-1-en-1-yl]-1-benzofuran-2-yl}formamido)propanoic acid

Traditional Name

2-({5,6-dihydroxy-4-[(1E)-prop-1-en-1-yl]-1-benzofuran-2-yl}formamido)propanoic acid

CAS Registry Number

Not Available

SMILES

C\C=C\C1=C2C=C(OC2=CC(O)=C1O)C(=O)NC(C)C(O)=O

InChI Identifier

InChI=1/C15H15NO6/c1-3-4-8-9-5-12(14(19)16-7(2)15(20)21)22-11(9)6-10(17)13(8)18/h3-7,17-18H,1-2H3,(H,16,19)(H,20,21)/b4-3+

InChI Key

GUHJREMXNVVWRT-ONEGZZNKNA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 500 MHz, C3D6O, experimental)	kishimoto@u-shizuoka-ken.ac.jp	University of Shizuoka	Shinji Kishimoto	2025-03-12	View Spectrum
HMBC NMR	[¹H, ¹³C] NMR Spectrum (2D, 500 MHz, C3D6O, experimental)	kishimoto@u-shizuoka-ken.ac.jp	University of Shizuoka	Shinji Kishimoto	2025-03-12	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, C3D6O, experimental)	kishimoto@u-shizuoka-ken.ac.jp	University of Shizuoka	Shinji Kishimoto	2025-03-12	View Spectrum
HSQC NMR	[¹H, ¹³C] NMR Spectrum (2D, 500 MHz, C3D6O, experimental)	kishimoto@u-shizuoka-ken.ac.jp	University of Shizuoka	Shinji Kishimoto	2025-03-12	View Spectrum
COSY NMR	[¹H, ¹H] NMR Spectrum (2D, 500 MHz, C3D6O, experimental)	kishimoto@u-shizuoka-ken.ac.jp	University of Shizuoka	Shinji Kishimoto	2025-03-12	View Spectrum

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Aspergillus lentulus		Not Available

Chemical Taxonomy

Classification

Not classified

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	1.69	ChemAxon
pKa (Strongest Acidic)	3.53	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	120 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	78.65 m³·mol⁻¹	ChemAxon
Polarizability	30.88 Å³	ChemAxon
Number of Rings	2	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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Kishimoto S, Minami A, Aoki Y, Matsubara Y, Watanabe S, Watanabe K: Reactive Azlactone Intermediate Drives Fungal Secondary Metabolite Cross-Pathway Generation. J Am Chem Soc. 2023 Feb 8;145(5):3221-3228. doi: 10.1021/jacs.2c13188. Epub 2023 Jan 27. [PubMed:36706030 ]
Kishimoto S: Non-enzymatic reactions in biogenesis of fungal natural products. J Nat Med. 2024 Jun;78(3):467-473. doi: 10.1007/s11418-024-01797-z. Epub 2024 Mar 22. [PubMed:38517623 ]
DOI: 10.1021/jacs.2c13188

Showing NP-Card for Lentofuranine (NP0350826)

MOL for NP0350826 (Lentofuranine)

3D MOL for NP0350826 (Lentofuranine)

3D SDF for NP0350826 (Lentofuranine)

3D-SDF for NP0350826 (Lentofuranine)

PDB for NP0350826 (Lentofuranine)

3D PDB for NP0350826 (Lentofuranine)

SMILES for NP0350826 (Lentofuranine)

INCHI for NP0350826 (Lentofuranine)

Structure for NP0350826 (Lentofuranine)

3D Structure for NP0350826 (Lentofuranine)