NP-MRD: Showing NP-Card for (+)-Paeoniflorigenone (NP0057761)

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Record Information

Version

2.0

Created at

2022-04-28 03:09:42 UTC

Updated at

2022-04-28 03:09:42 UTC

NP-MRD ID

NP0057761

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(+)-Paeoniflorigenone

Description

[(1S,3S,6R,8S,10R)-8-hydroxy-3-methyl-5-oxo-2,9-dioxatricyclo[4.3.1.0³,⁸]Decan-10-yl]methyl benzoate belongs to the class of organic compounds known as benzoic acid esters. These are ester derivatives of benzoic acid. (+)-Paeoniflorigenone is found in Paeonia hybrida, Paeonia albiflora , Paeonia lactiflora wild , Paeonia peregrina, Paeonia suffruticosa ANDREWS and Paeonia tenuifolia. Based on a literature review very few articles have been published on [(1S,3S,6R,8S,10R)-8-hydroxy-3-methyl-5-oxo-2,9-dioxatricyclo[4.3.1.0³,⁸]Decan-10-yl]methyl benzoate.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652304282205092D          

 23 26  0  0  1  0            999 V2000
    1.3174    0.3686    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3347   -0.3557    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2032   -0.4909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7572    0.1761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5758    0.0740    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3717    0.9844    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8438    1.1322    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5291    1.5963    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7258    1.0269    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4964   -0.0555    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3918    0.5280    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5338    2.4213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2507    2.8297    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2554    3.6547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5433    4.0713    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9722    4.0631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9769    4.8881    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6938    5.2965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4059    4.8799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4011    4.0549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6843    3.6465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1313   -1.1553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1080    0.1328    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
  4  6  1  0  0  0  0
  6  7  1  1  0  0  0
  1  7  1  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  2 10  1  0  0  0  0
  9 11  1  1  0  0  0
  1 11  1  0  0  0  0
  8 12  1  1  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 16 21  1  0  0  0  0
  2 22  1  1  0  0  0
  1 23  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0057761

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@]12CC(=O)[C@@H]3C[C@]1(O)O[C@H](O2)[C@H]3COC(=O)C1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C17H18O6/c1-16-8-13(18)11-7-17(16,20)23-15(22-16)12(11)9-21-14(19)10-5-3-2-4-6-10/h2-6,11-12,15,20H,7-9H2,1H3/t11-,12+,15+,16+,17+/m1/s1

> <INCHI_KEY>
BANPEMKDTXIFRE-PQTROMPISA-N

> <FORMULA>
C17H18O6

> <MOLECULAR_WEIGHT>
318.325

> <EXACT_MASS>
318.1103383

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
41

> <JCHEM_AVERAGE_POLARIZABILITY>
19.546817687064852

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
[(1S,3S,6R,8S,10R)-8-hydroxy-3-methyl-5-oxo-2,9-dioxatricyclo[4.3.1.0^{3,8}]decan-10-yl]methyl benzoate

> <ALOGPS_LOGP>
0.86

> <JCHEM_LOGP>
2.1250527573333335

> <ALOGPS_LOGS>
-1.85

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.196181333681654

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.876343593220733

> <JCHEM_PKA_STRONGEST_BASIC>
-4.16942926127861

> <JCHEM_POLAR_SURFACE_AREA>
82.06

> <JCHEM_REFRACTIVITY>
78.37090000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.45e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[(1S,3S,6R,8S,10R)-8-hydroxy-3-methyl-5-oxo-2,9-dioxatricyclo[4.3.1.0^{3,8}]decan-10-yl]methyl benzoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0       2.459   0.688   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.492  -0.664   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.113  -0.916   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.147   0.329   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       6.675   0.138   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       4.427   1.838   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.442   2.113   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.854   2.980   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.355   1.917   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       0.927  -0.104   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       0.731   0.986   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       2.863   4.520   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       4.201   5.282   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       4.210   6.822   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       2.881   7.600   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       5.548   7.584   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.557   9.124   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.895   9.887   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       8.224   9.109   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       8.215   7.569   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       6.877   6.807   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       2.112  -2.156   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       3.935   0.248   0.000  0.00  0.00           O+0
CONECT    1    2    7   11   23                                             
CONECT    2    1    3   10   22                                             
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7    8                                                  
CONECT    7    6    1                                                       
CONECT    8    6    9   12                                                  
CONECT    9    8   10   11                                                  
CONECT   10    9    2                                                       
CONECT   11    9    1                                                       
CONECT   12    8   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17   21                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   16                                                       
CONECT   22    2                                                            
CONECT   23    1                                                            
MASTER        0    0    0    0    0    0    0    0   23    0   52    0
END

View in JSmol

Synonyms

Value	Source
[(1S,3S,6R,8S,10R)-8-Hydroxy-3-methyl-5-oxo-2,9-dioxatricyclo[4.3.1.0,]decan-10-yl]methyl benzoic acid	Generator

Chemical Formula

C₁₇H₁₈O₆

Average Mass

318.3250 Da

Monoisotopic Mass

318.11034 Da

IUPAC Name

[(1S,3S,6R,8S,10R)-8-hydroxy-3-methyl-5-oxo-2,9-dioxatricyclo[4.3.1.0^{3,8}]decan-10-yl]methyl benzoate

Traditional Name

[(1S,3S,6R,8S,10R)-8-hydroxy-3-methyl-5-oxo-2,9-dioxatricyclo[4.3.1.0^{3,8}]decan-10-yl]methyl benzoate

CAS Registry Number

Not Available

SMILES

C[C@]12CC(=O)[C@@H]3C[C@]1(O)O[C@H](O2)[C@H]3COC(=O)C1=CC=CC=C1

InChI Identifier

InChI=1S/C17H18O6/c1-16-8-13(18)11-7-17(16,20)23-15(22-16)12(11)9-21-14(19)10-5-3-2-4-6-10/h2-6,11-12,15,20H,7-9H2,1H3/t11-,12+,15+,16+,17+/m1/s1

InChI Key

BANPEMKDTXIFRE-PQTROMPISA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Paeonia hybrida	Plant	KNApSAcK
Paeonia lactiflora	Plant	KNApSAcK
Paeonia lactiflora wild	Plant	KNApSAcK
Paeonia peregrina	Plant	KNApSAcK
Paeonia suffruticosa	Plant	KNApSAcK
Paeonia tenuifolia	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as benzoic acid esters. These are ester derivatives of benzoic acid.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Benzoic acids and derivatives

Direct Parent

Benzoic acid esters

Alternative Parents

Substituents

Benzoate ester
Benzoyl
Oxepane
Oxane
Cyclic alcohol
Meta-dioxolane
Ketone
Hemiacetal
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Acetal
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
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
logP	0.86	ALOGPS
logP	2.13	ChemAxon
logS	-1.8	ALOGPS
pKa (Strongest Acidic)	10.88	ChemAxon
pKa (Strongest Basic)	-4.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	82.06 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	78.37 m³·mol⁻¹	ChemAxon
Polarizability	19.55 Å³	ChemAxon
Number of Rings	4	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

157288674

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for (+)-Paeoniflorigenone (NP0057761)

MOL for NP0057761 ((+)-Paeoniflorigenone)

3D MOL for NP0057761 ((+)-Paeoniflorigenone)

3D SDF for NP0057761 ((+)-Paeoniflorigenone)

3D-SDF for NP0057761 ((+)-Paeoniflorigenone)

PDB for NP0057761 ((+)-Paeoniflorigenone)

3D PDB for NP0057761 ((+)-Paeoniflorigenone)

SMILES for NP0057761 ((+)-Paeoniflorigenone)

INCHI for NP0057761 ((+)-Paeoniflorigenone)

Structure for NP0057761 ((+)-Paeoniflorigenone)

3D Structure for NP0057761 ((+)-Paeoniflorigenone)