NP-MRD: Showing NP-Card for Wallifoliol (NP0078813)

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Record Information

Version

2.0

Created at

2022-04-28 23:53:54 UTC

Updated at

2022-04-28 23:53:54 UTC

NP-MRD ID

NP0078813

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Wallifoliol

Description

Wallifoliol belongs to the class of organic compounds known as benzoic acid esters. These are ester derivatives of benzoic acid. Wallifoliol is found in Curvularia lunata, Taxus canadensis, Taxus sumatrana and Taxus wallichiana . Wallifoliol was first documented in 2002 (PMID: 12502326). Based on a literature review very few articles have been published on Wallifoliol (PMID: 20527910).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304292201542D          

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M  END

     RDKit          3D

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  Mrv1652304292201542D          

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  4  8  1  6  0  0  0
  8  9  1  0  0  0  0
  3  9  1  0  0  0  0
  3 10  1  1  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
  2 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  1  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 15 19  1  0  0  0  0
 18 20  1  6  0  0  0
 17 21  1  0  0  0  0
 16 22  1  0  0  0  0
  1 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 23 25  1  0  0  0  0
 25 26  1  0  0  0  0
 15 26  1  0  0  0  0
 26 27  1  0  0  0  0
 26 28  1  0  0  0  0
 22 29  1  1  0  0  0
 14 30  1  1  0  0  0
 30 31  1  0  0  0  0
 31 32  2  0  0  0  0
 31 33  1  0  0  0  0
 33 34  2  0  0  0  0
 34 35  1  0  0  0  0
 35 36  2  0  0  0  0
 36 37  1  0  0  0  0
 37 38  2  0  0  0  0
 33 38  1  0  0  0  0
  1 39  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0078813

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)O[C@@]12CO[C@@H]1C[C@H](O)[C@]1(C)[C@@H]2[C@H](OC(=O)C2=CC=CC=C2)[C@]23C[C@H](O)C(C)=C2[C@@]1(O)C(=O)OC3(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C29H34O10/c1-14-17(31)12-27-20(14)29(35,24(34)39-25(27,3)4)26(5)18(32)11-19-28(13-36-19,38-15(2)30)21(26)22(27)37-23(33)16-9-7-6-8-10-16/h6-10,17-19,21-22,31-32,35H,11-13H2,1-5H3/t17-,18-,19+,21-,22-,26+,27-,28-,29+/m0/s1

> <INCHI_KEY>
CIHPBJOPSVVYIO-RFIZPCKGSA-N

> <FORMULA>
C29H34O10

> <MOLECULAR_WEIGHT>
542.581

> <EXACT_MASS>
542.215197295

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
73

> <JCHEM_AVERAGE_POLARIZABILITY>
53.89741241428955

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,2S,3R,4S,7R,9S,10S,11S,14S)-4-(acetyloxy)-9,11,14-trihydroxy-10,13,16,16-tetramethyl-18-oxo-6,17-dioxapentacyclo[9.4.3.0^{1,12}.0^{3,10}.0^{4,7}]octadec-12-en-2-yl benzoate

> <ALOGPS_LOGP>
1.56

> <JCHEM_LOGP>
0.5961537556666672

> <ALOGPS_LOGS>
-3.19

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.272978591378727

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.391603362609786

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9950061438714934

> <JCHEM_POLAR_SURFACE_AREA>
148.82

> <JCHEM_REFRACTIVITY>
133.91

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.54e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2S,3R,4S,7R,9S,10S,11S,14S)-4-(acetyloxy)-9,11,14-trihydroxy-10,13,16,16-tetramethyl-18-oxo-6,17-dioxapentacyclo[9.4.3.0^{1,12}.0^{3,10}.0^{4,7}]octadec-12-en-2-yl benzoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 29-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-APR-22         0                                  
HETATM    1  C   UNK     0       4.403  -0.071   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.902   1.154   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.510   1.564   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.454   0.347   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.872  -1.079   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.346  -1.288   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       5.718  -2.937   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0       8.671   1.291   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       7.727   2.508   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       6.505   3.439   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       7.547   4.815   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       6.948   6.234   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       9.075   4.625   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.388   2.775   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.962   3.357   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.343   1.865   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.880   1.766   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.449   3.197   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.263   4.181   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       7.435   3.469   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       5.974   0.741   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       2.983  -0.667   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       1.557  -0.085   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       0.151  -0.979   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0       0.960   1.335   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       1.542   2.760   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -0.023   3.337   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       0.792   4.266   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       2.037  -2.116   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0       5.002   4.831   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       4.412   6.417   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       2.893   6.673   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       5.393   7.604   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       4.855   9.047   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       5.836  10.234   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       7.355   9.978   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       7.892   8.535   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       6.911   7.348   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       3.942  -1.762   0.000  0.00  0.00           C+0
CONECT    1    2    6   22   39                                             
CONECT    2    1    3   14                                                  
CONECT    3    2    4    9   10                                             
CONECT    4    3    5    8                                                  
CONECT    5    4    6                                                       
CONECT    6    5    1    7                                                  
CONECT    7    6                                                            
CONECT    8    4    9                                                       
CONECT    9    8    3                                                       
CONECT   10    3   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11                                                            
CONECT   14    2   15   30                                                  
CONECT   15   14   16   19   26                                             
CONECT   16   15   17   22                                                  
CONECT   17   16   18   21                                                  
CONECT   18   17   19   20                                                  
CONECT   19   18   15                                                       
CONECT   20   18                                                            
CONECT   21   17                                                            
CONECT   22   16    1   23   29                                             
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26                                                       
CONECT   26   25   15   27   28                                             
CONECT   27   26                                                            
CONECT   28   26                                                            
CONECT   29   22                                                            
CONECT   30   14   31                                                       
CONECT   31   30   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31   34   38                                                  
CONECT   34   33   35                                                       
CONECT   35   34   36                                                       
CONECT   36   35   37                                                       
CONECT   37   36   38                                                       
CONECT   38   37   33                                                       
CONECT   39    1                                                            
MASTER        0    0    0    0    0    0    0    0   39    0   88    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₉H₃₄O₁₀

Average Mass

542.5810 Da

Monoisotopic Mass

542.21520 Da

IUPAC Name

(1S,2S,3R,4S,7R,9S,10S,11S,14S)-4-(acetyloxy)-9,11,14-trihydroxy-10,13,16,16-tetramethyl-18-oxo-6,17-dioxapentacyclo[9.4.3.0^{1,12}.0^{3,10}.0^{4,7}]octadec-12-en-2-yl benzoate

Traditional Name

(1S,2S,3R,4S,7R,9S,10S,11S,14S)-4-(acetyloxy)-9,11,14-trihydroxy-10,13,16,16-tetramethyl-18-oxo-6,17-dioxapentacyclo[9.4.3.0^{1,12}.0^{3,10}.0^{4,7}]octadec-12-en-2-yl benzoate

CAS Registry Number

Not Available

SMILES

CC(=O)O[C@@]12CO[C@@H]1C[C@H](O)[C@]1(C)[C@@H]2[C@H](OC(=O)C2=CC=CC=C2)[C@]23C[C@H](O)C(C)=C2[C@@]1(O)C(=O)OC3(C)C

InChI Identifier

InChI=1S/C29H34O10/c1-14-17(31)12-27-20(14)29(35,24(34)39-25(27,3)4)26(5)18(32)11-19-28(13-36-19,38-15(2)30)21(26)22(27)37-23(33)16-9-7-6-8-10-16/h6-10,17-19,21-22,31-32,35H,11-13H2,1-5H3/t17-,18-,19+,21-,22-,26+,27-,28-,29+/m0/s1

InChI Key

CIHPBJOPSVVYIO-RFIZPCKGSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Curvularia lunata	LOTUS Database	35616633
Taxus canadensis	Plant	KNApSAcK
Taxus sumatrana	Plant	KNApSAcK
Taxus wallichiana	Plant	KNApSAcK

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
Tricarboxylic acid or derivatives
Benzoyl
Delta valerolactone
Delta_valerolactone
Oxane
Cyclic alcohol
Tertiary alcohol
Carboxylic acid ester
Lactone
Secondary alcohol
Oxetane
Organoheterocyclic compound
Ether
Dialkyl ether
Oxacycle
Carboxylic acid derivative
Polyol
Hydrocarbon derivative
Alcohol
Carbonyl group
Organooxygen compound
Organic oxygen compound
Organic oxide
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	1.56	ALOGPS
logP	0.6	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	11.39	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	148.82 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	133.91 m³·mol⁻¹	ChemAxon
Polarizability	53.9 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	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

C00043117

Chemspider ID

10285161

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

21673419

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Shen YC, Wang SS, Pan YL, Lo KL, Chakraborty R, Chien CT, Kuo YH, Lin YC: New taxane diterpenoids from the leaves and twigs of Taxus sumatrana. J Nat Prod. 2002 Dec;65(12):1848-52. doi: 10.1021/np0202273. [PubMed:12502326 ]
Arnone A, Bava A, Fronza G, Malpezzi L, Nasini G: Microbial transformations of the taxan ring of 10-DAB by some strains of the fungus Curvularia lunata: formation of the bis-abeotaxanes wallifoliol and 4-deacylwallifoliol. J Nat Prod. 2010 Jun 25;73(6):1049-52. doi: 10.1021/np900765y. [PubMed:20527910 ]

Showing NP-Card for Wallifoliol (NP0078813)

MOL for NP0078813 (Wallifoliol)

3D MOL for NP0078813 (Wallifoliol)

3D SDF for NP0078813 (Wallifoliol)

3D-SDF for NP0078813 (Wallifoliol)

PDB for NP0078813 (Wallifoliol)

3D PDB for NP0078813 (Wallifoliol)

SMILES for NP0078813 (Wallifoliol)

INCHI for NP0078813 (Wallifoliol)

Structure for NP0078813 (Wallifoliol)

3D Structure for NP0078813 (Wallifoliol)