NP-MRD: Showing NP-Card for Platanic acid (NP0064273)

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Record Information

Version

2.0

Created at

2022-04-28 08:32:14 UTC

Updated at

2022-04-28 08:32:14 UTC

NP-MRD ID

NP0064273

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Platanic acid

Description

ZINC253500929 belongs to the class of organic compounds known as oxosteroids. These are steroid derivatives carrying a C=O group attached to steroid skeleton. Platanic acid is found in Arbutus unedo, Breynia fruticosa, Eugenia moraviana, Leptospermum scoparium, Melaleuca ericifolia, Melaleuca leucadendra, Melaleuca leucadendron , Melilotus messanensis, Platanus occidentalis and Syzigium claviflorum. Based on a literature review very few articles have been published on ZINC253500929.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282210322D          

 33 37  0  0  1  0            999 V2000
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  3 31  1  0  0  0  0
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  2 33  1  1  0  0  0
M  END

     RDKit          3D

 79 83  0  0  0  0  0  0  0  0999 V2000
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M  END


  Mrv1652304282210322D          

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 21 22  1  6  0  0  0
 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
 16 25  1  1  0  0  0
 25 26  2  0  0  0  0
 25 27  1  0  0  0  0
 11 28  1  6  0  0  0
  8 29  1  1  0  0  0
  5 30  1  1  0  0  0
  3 31  1  0  0  0  0
  3 32  1  0  0  0  0
  2 33  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0064273

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)[C@@H]1CC[C@@]2(CC[C@]3(C)[C@H](CC[C@@H]4[C@@]5(C)CC[C@H](O)C(C)(C)[C@H]5CC[C@@]34C)[C@H]12)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C29H46O4/c1-17(30)18-9-14-29(24(32)33)16-15-27(5)19(23(18)29)7-8-21-26(4)12-11-22(31)25(2,3)20(26)10-13-28(21,27)6/h18-23,31H,7-16H2,1-6H3,(H,32,33)/t18-,19+,20+,21+,22-,23-,26-,27+,28+,29-/m0/s1

> <INCHI_KEY>
RVMPLOSJMIQORE-ISZXNJLNSA-N

> <FORMULA>
C29H46O4

> <MOLECULAR_WEIGHT>
458.683

> <EXACT_MASS>
458.339609961

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
79

> <JCHEM_AVERAGE_POLARIZABILITY>
53.02156423999929

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,2R,5S,8R,9R,10R,13R,14R,17S,19S)-8-acetyl-17-hydroxy-1,2,14,18,18-pentamethylpentacyclo[11.8.0.0^{2,10}.0^{5,9}.0^{14,19}]henicosane-5-carboxylic acid

> <ALOGPS_LOGP>
4.86

> <JCHEM_LOGP>
5.521148069333333

> <ALOGPS_LOGS>
-5.54

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
19.42356970991523

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.578571079163897

> <JCHEM_PKA_STRONGEST_BASIC>
-0.8351233785945736

> <JCHEM_POLAR_SURFACE_AREA>
74.60000000000001

> <JCHEM_REFRACTIVITY>
128.9408

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.33e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2R,5S,8R,9R,10R,13R,14R,17S,19S)-8-acetyl-17-hydroxy-1,2,14,18,18-pentamethylpentacyclo[11.8.0.0^{2,10}.0^{5,9}.0^{14,19}]henicosane-5-carboxylic acid

> <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       9.931   1.521   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      10.681   2.866   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       9.890   4.188   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.351   4.165   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.601   2.819   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.391   1.498   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.061   2.796   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.271   4.118   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.021   5.463   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.560   5.486   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.731   4.094   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.982   2.749   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.772   1.427   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.312   1.451   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.442   2.726   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.651   4.048   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.401   5.393   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.941   5.416   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -0.850   3.704   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -0.987   2.171   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       0.429   1.566   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       0.772   0.064   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      -0.357  -0.983   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       2.244  -0.389   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -0.273   5.280   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       0.332   6.696   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0      -1.801   5.095   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       4.481   5.440   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       5.409   5.652   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       6.851   1.474   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       9.921   5.728   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      11.184   5.024   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      12.220   2.890   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3   33                                                  
CONECT    3    2    4   31   32                                             
CONECT    4    3    5   10                                                  
CONECT    5    4    6    7   30                                             
CONECT    6    5    1                                                       
CONECT    7    5    8   14                                                  
CONECT    8    7    9   11   29                                             
CONECT    9    8   10                                                       
CONECT   10    9    4                                                       
CONECT   11    8   12   18   28                                             
CONECT   12   11   13   15                                                  
CONECT   13   12   14                                                       
CONECT   14   13    7                                                       
CONECT   15   12   16   21                                                  
CONECT   16   15   17   19   25                                             
CONECT   17   16   18                                                       
CONECT   18   17   11                                                       
CONECT   19   16   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   15   22                                                  
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22                                                            
CONECT   25   16   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25                                                            
CONECT   28   11                                                            
CONECT   29    8                                                            
CONECT   30    5                                                            
CONECT   31    3                                                            
CONECT   32    3                                                            
CONECT   33    2                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   74    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₉H₄₆O₄

Average Mass

458.6830 Da

Monoisotopic Mass

458.33961 Da

IUPAC Name

(1R,2R,5S,8R,9R,10R,13R,14R,17S,19S)-8-acetyl-17-hydroxy-1,2,14,18,18-pentamethylpentacyclo[11.8.0.0^{2,10}.0^{5,9}.0^{14,19}]henicosane-5-carboxylic acid

Traditional Name

(1R,2R,5S,8R,9R,10R,13R,14R,17S,19S)-8-acetyl-17-hydroxy-1,2,14,18,18-pentamethylpentacyclo[11.8.0.0^{2,10}.0^{5,9}.0^{14,19}]henicosane-5-carboxylic acid

CAS Registry Number

Not Available

SMILES

CC(=O)[C@@H]1CC[C@@]2(CC[C@]3(C)[C@H](CC[C@@H]4[C@@]5(C)CC[C@H](O)C(C)(C)[C@H]5CC[C@@]34C)[C@H]12)C(O)=O

InChI Identifier

InChI=1S/C29H46O4/c1-17(30)18-9-14-29(24(32)33)16-15-27(5)19(23(18)29)7-8-21-26(4)12-11-22(31)25(2,3)20(26)10-13-28(21,27)6/h18-23,31H,7-16H2,1-6H3,(H,32,33)/t18-,19+,20+,21+,22-,23-,26-,27+,28+,29-/m0/s1

InChI Key

RVMPLOSJMIQORE-ISZXNJLNSA-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
Arbutus unedo	LOTUS Database	35616633
Breynia fruticosa	LOTUS Database	35616633
Eugenia moraviana	LOTUS Database	35616633
Leptospermum scoparium	LOTUS Database	35616633
Melaleuca ericifolia	Plant	KNApSAcK
Melaleuca leucadendra	LOTUS Database	35616633
Melaleuca leucadendron	Plant	KNApSAcK
Melilotus messanensis	LOTUS Database	35616633
Platanus occidentalis	Plant	KNApSAcK
Syzigium claviflorum	-	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as oxosteroids. These are steroid derivatives carrying a C=O group attached to steroid skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Oxosteroids

Direct Parent

Oxosteroids

Alternative Parents

Substituents

18-hydroxysteroid
18-oxosteroid
Oxosteroid
Hydroxysteroid
Monoterpenoid
11-noriridane monoterpenoid
Cyclic alcohol
Secondary alcohol
Ketone
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic 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	4.86	ALOGPS
logP	5.52	ChemAxon
logS	-5.5	ALOGPS
pKa (Strongest Acidic)	4.58	ChemAxon
pKa (Strongest Basic)	-0.84	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	74.6 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	128.94 m³·mol⁻¹	ChemAxon
Polarizability	53.02 Å³	ChemAxon
Number of Rings	5	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

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

124900004

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Platanic acid (NP0064273)

MOL for NP0064273 (Platanic acid)

3D MOL for NP0064273 (Platanic acid)

3D SDF for NP0064273 (Platanic acid)

3D-SDF for NP0064273 (Platanic acid)

PDB for NP0064273 (Platanic acid)

3D PDB for NP0064273 (Platanic acid)

SMILES for NP0064273 (Platanic acid)

INCHI for NP0064273 (Platanic acid)

Structure for NP0064273 (Platanic acid)

3D Structure for NP0064273 (Platanic acid)