NP-MRD: Showing NP-Card for (2s)-5-hydroxy-2-[(4-hydroxyphenyl)methyl]-4-[(2e,4e)-1,6,7-trihydroxy-2,4,6-trimethylocta-2,4-dien-1-ylidene]-2h-pyrrol-3-one (NP0220760)

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Record Information

Version

2.0

Created at

2022-09-05 22:09:53 UTC

Updated at

2022-09-05 22:09:54 UTC

NP-MRD ID

NP0220760

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2s)-5-hydroxy-2-[(4-hydroxyphenyl)methyl]-4-[(2e,4e)-1,6,7-trihydroxy-2,4,6-trimethylocta-2,4-dien-1-ylidene]-2h-pyrrol-3-one

Description

Prototenellin C belongs to the class of organic compounds known as 1-hydroxy-2-unsubstituted benzenoids. These are phenols that are unsubstituted at the 2-position. Based on a literature review very few articles have been published on Prototenellin C.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309062200092D          

 29 30  0  0  1  0            999 V2000
   -0.1067    0.7634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6078    1.1759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6078    2.0009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1067    2.4134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5192    1.6989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3058    3.1279    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8212    2.8259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8212    3.6509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5356    2.4134    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3222    0.7634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3222   -0.0616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6078   -0.4741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0367   -0.4741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7512   -0.0616    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0367   -1.2991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7041   -1.7840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4888   -1.5291    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4492   -2.5687    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.9341   -3.2361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5986   -3.9898    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0835   -4.6572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7479   -5.4109    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9275   -5.4971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5919   -6.2508    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4425   -4.8297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7781   -4.0760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6242   -2.5687    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3693   -1.7840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5846   -1.5291    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
  4  6  1  0  0  0  0
  4  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  2 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  4  0  0  0
 13 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
 18 19  1  6  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 23 25  1  0  0  0  0
 25 26  2  0  0  0  0
 20 26  1  0  0  0  0
 18 27  1  0  0  0  0
 27 28  2  0  0  0  0
 15 28  1  0  0  0  0
 28 29  1  0  0  0  0
M  END


  Mrv1652309062200092D          

 29 30  0  0  1  0            999 V2000
   -0.1067    0.7634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6078    1.1759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6078    2.0009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1067    2.4134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5192    1.6989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3058    3.1279    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8212    2.8259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8212    3.6509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5356    2.4134    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3222    0.7634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3222   -0.0616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6078   -0.4741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0367   -0.4741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7512   -0.0616    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0367   -1.2991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7041   -1.7840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4888   -1.5291    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4492   -2.5687    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.9341   -3.2361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5986   -3.9898    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0835   -4.6572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7479   -5.4109    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9275   -5.4971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5919   -6.2508    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4425   -4.8297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7781   -4.0760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6242   -2.5687    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3693   -1.7840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5846   -1.5291    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
  4  6  1  0  0  0  0
  4  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  2 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  4  0  0  0
 13 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
 18 19  1  6  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 23 25  1  0  0  0  0
 25 26  2  0  0  0  0
 20 26  1  0  0  0  0
 18 27  1  0  0  0  0
 27 28  2  0  0  0  0
 15 28  1  0  0  0  0
 28 29  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0220760

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(O)C(C)(O)\C=C(/C)\C=C(/C)C(O)=C1C(O)=N[C@@H](CC2=CC=C(O)C=C2)C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C22H27NO6/c1-12(11-22(4,29)14(3)24)9-13(2)19(26)18-20(27)17(23-21(18)28)10-15-5-7-16(25)8-6-15/h5-9,11,14,17,24-26,29H,10H2,1-4H3,(H,23,28)/b12-11+,13-9+,19-18?/t14?,17-,22?/m0/s1

> <INCHI_KEY>
VZEQENBPVTXTLV-SFQDIMNPSA-N

> <FORMULA>
C22H27NO6

> <MOLECULAR_WEIGHT>
401.459

> <EXACT_MASS>
401.183837593

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
56

> <JCHEM_AVERAGE_POLARIZABILITY>
43.000489734267404

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2S)-5-hydroxy-2-[(4-hydroxyphenyl)methyl]-4-[(2E,4E)-1,6,7-trihydroxy-2,4,6-trimethylocta-2,4-dien-1-ylidene]-3,4-dihydro-2H-pyrrol-3-one

> <JCHEM_LOGP>
2.351995373666667

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
9.255327877883376

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.9170368410264973

> <JCHEM_PKA_STRONGEST_BASIC>
0.6654131934469265

> <JCHEM_POLAR_SURFACE_AREA>
130.57999999999998

> <JCHEM_REFRACTIVITY>
112.2533

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(2S)-5-hydroxy-2-[(4-hydroxyphenyl)methyl]-4-[(2E,4E)-1,6,7-trihydroxy-2,4,6-trimethylocta-2,4-dien-1-ylidene]-2H-pyrrol-3-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-SEP-22         0                                  
HETATM    1  C   UNK     0      -0.199   1.425   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.134   2.195   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.134   3.735   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.199   4.505   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.969   3.171   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       0.571   5.839   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      -1.533   5.275   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.533   6.815   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -2.867   4.505   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       2.468   1.425   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.468  -0.115   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.134  -0.885   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.802  -0.885   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       5.136  -0.115   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       3.802  -2.425   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.048  -3.330   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       6.512  -2.854   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       4.572  -4.795   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.477  -6.041   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.851  -7.448   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       5.756  -8.693   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       5.129 -10.100   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       3.598 -10.261   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       2.972 -11.668   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       2.693  -9.015   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       3.319  -7.609   0.000  0.00  0.00           C+0
HETATM   27  N   UNK     0       3.032  -4.795   0.000  0.00  0.00           N+0
HETATM   28  C   UNK     0       2.556  -3.330   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       1.091  -2.854   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   10                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    6    7                                             
CONECT    5    4                                                            
CONECT    6    4                                                            
CONECT    7    4    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7                                                            
CONECT   10    2   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16   28                                                  
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19   27                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21   26                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26                                                       
CONECT   26   25   20                                                       
CONECT   27   18   28                                                       
CONECT   28   27   15   29                                                  
CONECT   29   28                                                            
MASTER        0    0    0    0    0    0    0    0   29    0   60    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₂H₂₇NO₆

Average Mass

401.4590 Da

Monoisotopic Mass

401.18384 Da

IUPAC Name

(2S)-5-hydroxy-2-[(4-hydroxyphenyl)methyl]-4-[(2E,4E)-1,6,7-trihydroxy-2,4,6-trimethylocta-2,4-dien-1-ylidene]-3,4-dihydro-2H-pyrrol-3-one

Traditional Name

(2S)-5-hydroxy-2-[(4-hydroxyphenyl)methyl]-4-[(2E,4E)-1,6,7-trihydroxy-2,4,6-trimethylocta-2,4-dien-1-ylidene]-2H-pyrrol-3-one

CAS Registry Number

Not Available

SMILES

CC(O)C(C)(O)\C=C(/C)\C=C(/C)C(O)=C1C(O)=N[C@@H](CC2=CC=C(O)C=C2)C1=O

InChI Identifier

InChI=1S/C22H27NO6/c1-12(11-22(4,29)14(3)24)9-13(2)19(26)18-20(27)17(23-21(18)28)10-15-5-7-16(25)8-6-15/h5-9,11,14,17,24-26,29H,10H2,1-4H3,(H,23,28)/b12-11+,13-9+,19-18?/t14?,17-,22?/m0/s1

InChI Key

VZEQENBPVTXTLV-SFQDIMNPSA-N

Experimental Spectra

Not Available

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
Tertiary alcohol
Pyrrolidine
Cyclic ketone
Secondary carboxylic acid amide
Secondary alcohol
Lactam
Ketone
Carboxamide group
1,2-diol
Azacycle
Organoheterocyclic compound
Polyol
Enol
Carboxylic acid derivative
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
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
logP	2.35	ChemAxon
pKa (Strongest Acidic)	3.92	ChemAxon
pKa (Strongest Basic)	0.67	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	130.58 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	112.25 m³·mol⁻¹	ChemAxon
Polarizability	43 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

78436142

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

139583757

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2s)-5-hydroxy-2-[(4-hydroxyphenyl)methyl]-4-[(2e,4e)-1,6,7-trihydroxy-2,4,6-trimethylocta-2,4-dien-1-ylidene]-2h-pyrrol-3-one (NP0220760)

MOL for NP0220760 ((2s)-5-hydroxy-2-[(4-hydroxyphenyl)methyl]-4-[(2e,4e)-1,6,7-trihydroxy-2,4,6-trimethylocta-2,4-dien-1-ylidene]-2h-pyrrol-3-one)

3D MOL for NP0220760 ((2s)-5-hydroxy-2-[(4-hydroxyphenyl)methyl]-4-[(2e,4e)-1,6,7-trihydroxy-2,4,6-trimethylocta-2,4-dien-1-ylidene]-2h-pyrrol-3-one)

3D SDF for NP0220760 ((2s)-5-hydroxy-2-[(4-hydroxyphenyl)methyl]-4-[(2e,4e)-1,6,7-trihydroxy-2,4,6-trimethylocta-2,4-dien-1-ylidene]-2h-pyrrol-3-one)

3D-SDF for NP0220760 ((2s)-5-hydroxy-2-[(4-hydroxyphenyl)methyl]-4-[(2e,4e)-1,6,7-trihydroxy-2,4,6-trimethylocta-2,4-dien-1-ylidene]-2h-pyrrol-3-one)

PDB for NP0220760 ((2s)-5-hydroxy-2-[(4-hydroxyphenyl)methyl]-4-[(2e,4e)-1,6,7-trihydroxy-2,4,6-trimethylocta-2,4-dien-1-ylidene]-2h-pyrrol-3-one)

3D PDB for NP0220760 ((2s)-5-hydroxy-2-[(4-hydroxyphenyl)methyl]-4-[(2e,4e)-1,6,7-trihydroxy-2,4,6-trimethylocta-2,4-dien-1-ylidene]-2h-pyrrol-3-one)

SMILES for NP0220760 ((2s)-5-hydroxy-2-[(4-hydroxyphenyl)methyl]-4-[(2e,4e)-1,6,7-trihydroxy-2,4,6-trimethylocta-2,4-dien-1-ylidene]-2h-pyrrol-3-one)

INCHI for NP0220760 ((2s)-5-hydroxy-2-[(4-hydroxyphenyl)methyl]-4-[(2e,4e)-1,6,7-trihydroxy-2,4,6-trimethylocta-2,4-dien-1-ylidene]-2h-pyrrol-3-one)

Structure for NP0220760 ((2s)-5-hydroxy-2-[(4-hydroxyphenyl)methyl]-4-[(2e,4e)-1,6,7-trihydroxy-2,4,6-trimethylocta-2,4-dien-1-ylidene]-2h-pyrrol-3-one)

3D Structure for NP0220760 ((2s)-5-hydroxy-2-[(4-hydroxyphenyl)methyl]-4-[(2e,4e)-1,6,7-trihydroxy-2,4,6-trimethylocta-2,4-dien-1-ylidene]-2h-pyrrol-3-one)