NP-MRD: Showing NP-Card for 3,5,7-trihydroxy-7-methyl-2-[(1e)-pent-1-en-1-yl]pyrano[2,3-c]pyrrol-4-one (NP0280495)

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Record Information

Version

2.0

Created at

2022-09-09 06:19:10 UTC

Updated at

2022-09-09 06:19:10 UTC

NP-MRD ID

NP0280495

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3,5,7-trihydroxy-7-methyl-2-[(1e)-pent-1-en-1-yl]pyrano[2,3-c]pyrrol-4-one

Description

7-Hydroxycordylactam belongs to the class of organic compounds known as pyranones and derivatives. Pyranones and derivatives are compounds containing a pyran ring which bears a ketone. 3,5,7-trihydroxy-7-methyl-2-[(1e)-pent-1-en-1-yl]pyrano[2,3-c]pyrrol-4-one is found in Warcupiella spinulosa. 3,5,7-trihydroxy-7-methyl-2-[(1e)-pent-1-en-1-yl]pyrano[2,3-c]pyrrol-4-one was first documented in 2022 (PMID: 33280415). Based on a literature review very few articles have been published on 7-hydroxycordylactam.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309092208192D          

 19 20  0  0  0  0            999 V2000
    5.6424    0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9279    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2135    0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4990    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    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 O   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 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7845    2.3479    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435    2.1904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3984    2.9750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6284    1.5229    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435    0.8555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7508    0.2971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0196    0.0468    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  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
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
  6 12  2  0  0  0  0
 12 13  1  0  0  0  0
  9 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  2  0  0  0  0
 16 17  1  0  0  0  0
  8 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0280495

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCC\C=C\C1=C(O)C(=O)C2=C(O1)C(C)(O)N=C2O

> <INCHI_IDENTIFIER>
InChI=1S/C13H15NO5/c1-3-4-5-6-7-9(15)10(16)8-11(19-7)13(2,18)14-12(8)17/h5-6,15,18H,3-4H2,1-2H3,(H,14,17)/b6-5+

> <INCHI_KEY>
JNKJMYDDORVXSD-AATRIKPKSA-N

> <FORMULA>
C13H15NO5

> <MOLECULAR_WEIGHT>
265.265

> <EXACT_MASS>
265.095022587

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
34

> <JCHEM_AVERAGE_POLARIZABILITY>
27.05339671329087

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3,5,7-trihydroxy-7-methyl-2-[(1E)-pent-1-en-1-yl]-4H,7H-pyrano[2,3-c]pyrrol-4-one

> <JCHEM_LOGP>
1.5778013759999996

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.679331143520796

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.23637302390285

> <JCHEM_PKA_STRONGEST_BASIC>
-3.0296561612920785

> <JCHEM_POLAR_SURFACE_AREA>
99.35000000000001

> <JCHEM_REFRACTIVITY>
71.47970000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
3,5,7-trihydroxy-7-methyl-2-[(1E)-pent-1-en-1-yl]pyrano[2,3-c]pyrrol-4-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 09-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   09-SEP-22         0                                  
HETATM    1  C   UNK     0      10.533   1.303   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.199   2.073   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.865   1.303   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.531   2.073   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.198   1.303   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.864   2.073   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       2.530   1.303   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       1.197   2.073   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.197   3.613   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.530   4.383   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       2.530   5.923   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       3.864   3.613   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       5.198   4.383   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      -0.268   4.089   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -0.744   5.553   0.000  0.00  0.00           O+0
HETATM   16  N   UNK     0      -1.173   2.843   0.000  0.00  0.00           N+0
HETATM   17  C   UNK     0      -0.268   1.597   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -1.401   0.555   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       0.037   0.087   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   12                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   17                                                  
CONECT    9    8   10   14                                                  
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10    6   13                                                  
CONECT   13   12                                                            
CONECT   14    9   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17                                                       
CONECT   17   16    8   18   19                                             
CONECT   18   17                                                            
CONECT   19   17                                                            
MASTER        0    0    0    0    0    0    0    0   19    0   40    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₃H₁₅NO₅

Average Mass

265.2650 Da

Monoisotopic Mass

265.09502 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

CCC\C=C\C1=C(O)C(=O)C2=C(O1)C(C)(O)N=C2O

InChI Identifier

InChI=1S/C13H15NO5/c1-3-4-5-6-7-9(15)10(16)8-11(19-7)13(2,18)14-12(8)17/h5-6,15,18H,3-4H2,1-2H3,(H,14,17)/b6-5+

InChI Key

JNKJMYDDORVXSD-AATRIKPKSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Warcupiella spinulosa	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pyranones and derivatives. Pyranones and derivatives are compounds containing a pyran ring which bears a ketone.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Pyrans

Sub Class

Pyranones and derivatives

Direct Parent

Pyranones and derivatives

Alternative Parents

Substituents

Pyranone
Heteroaromatic compound
Secondary carboxylic acid amide
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
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

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

146684239

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Nord C, Levenfors JJ, Bjerketorp J, Guss B, Oberg B, Broberg A: Tetramic acid based alkaloids from Aspergillus amoenus Roberg strain UP197 - antibiotic properties and new pyranterreones. Nat Prod Res. 2022 Feb;36(4):967-973. doi: 10.1080/14786419.2020.1855643. Epub 2020 Dec 7. [PubMed:33280415 ]
LOTUS database [Link]

Showing NP-Card for 3,5,7-trihydroxy-7-methyl-2-[(1e)-pent-1-en-1-yl]pyrano[2,3-c]pyrrol-4-one (NP0280495)

MOL for NP0280495 (3,5,7-trihydroxy-7-methyl-2-[(1e)-pent-1-en-1-yl]pyrano[2,3-c]pyrrol-4-one)

3D MOL for NP0280495 (3,5,7-trihydroxy-7-methyl-2-[(1e)-pent-1-en-1-yl]pyrano[2,3-c]pyrrol-4-one)

3D SDF for NP0280495 (3,5,7-trihydroxy-7-methyl-2-[(1e)-pent-1-en-1-yl]pyrano[2,3-c]pyrrol-4-one)

3D-SDF for NP0280495 (3,5,7-trihydroxy-7-methyl-2-[(1e)-pent-1-en-1-yl]pyrano[2,3-c]pyrrol-4-one)

PDB for NP0280495 (3,5,7-trihydroxy-7-methyl-2-[(1e)-pent-1-en-1-yl]pyrano[2,3-c]pyrrol-4-one)

3D PDB for NP0280495 (3,5,7-trihydroxy-7-methyl-2-[(1e)-pent-1-en-1-yl]pyrano[2,3-c]pyrrol-4-one)

SMILES for NP0280495 (3,5,7-trihydroxy-7-methyl-2-[(1e)-pent-1-en-1-yl]pyrano[2,3-c]pyrrol-4-one)

INCHI for NP0280495 (3,5,7-trihydroxy-7-methyl-2-[(1e)-pent-1-en-1-yl]pyrano[2,3-c]pyrrol-4-one)

Structure for NP0280495 (3,5,7-trihydroxy-7-methyl-2-[(1e)-pent-1-en-1-yl]pyrano[2,3-c]pyrrol-4-one)

3D Structure for NP0280495 (3,5,7-trihydroxy-7-methyl-2-[(1e)-pent-1-en-1-yl]pyrano[2,3-c]pyrrol-4-one)