NP-MRD: Showing NP-Card for Ponasterone A (NP0052170)

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Record Information

Version

2.0

Created at

2022-04-27 23:19:29 UTC

Updated at

2022-04-27 23:19:29 UTC

NP-MRD ID

NP0052170

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Ponasterone A

Description

Ponasterone A belongs to the class of organic compounds known as pentahydroxy bile acids, alcohols and derivatives. These are bile acids, alcohols or derivatives bearing five hydroxyl groups. Thus, ponasterone a is considered to be a sterol lipid molecule. Ponasterone A is found in Afrocarpus gracilior, Bolbitis subcordata, Brainea insignis, Iotrochota birotulata, Limnanthes douglasii, Matteuccia struthiopteris , Osmunda japonica , Plenasium banksiaefolium, Plenasium banksiifolium, Podocarpus macrophyllus , Podocarpus macrophyllus var.maki , Podocarpus nakaii, Pteridium aquilinum, Pteridium aquilinum var.latiusculum , Tapinella panuoides, Taxus brevifolia , Taxus cuspidata , Taxus floridana, Taxus mairei, Taxus wallichiana, Woodwardia orientalis and Zoanthus sp.. Ponasterone A is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309272007272D          

 36 39  0  0  1  0            999 V2000
    6.3178   -6.0518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    6.3178   -7.7141    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0599   -7.2984    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.7723   -7.7141    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5142   -7.2984    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    7.0599   -6.4673    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
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   10.0110   -4.9540    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
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 10  9  1  0  0  0  0
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  6  7  1  0  0  0  0
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 16  6  2  0  0  0  0
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  3  4  1  0  0  0  0
  3  2  1  0  0  0  0
  2 17  1  1  0  0  0
  3 18  1  1  0  0  0
 21 22  1  0  0  0  0
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 12 22  1  0  0  0  0
 22 13  1  1  0  0  0
 23 19  1  6  0  0  0
  8 23  1  0  0  0  0
M  END

     RDKit          3D

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M  END


  Mrv1652309272007272D          

 36 39  0  0  1  0            999 V2000
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    5.5757   -6.4673    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
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  8  9  1  0  0  0  0
  9 15  1  6  0  0  0
 11  9  1  0  0  0  0
  7  8  2  0  0  0  0
  5 10  1  0  0  0  0
 10 14  1  1  0  0  0
  1 10  1  0  0  0  0
 11 12  1  0  0  0  0
  6  7  1  0  0  0  0
  4  5  1  0  0  0  0
  6  5  1  0  0  0  0
  5 20  1  1  0  0  0
 16  6  2  0  0  0  0
  2  1  1  0  0  0  0
  3  4  1  0  0  0  0
  3  2  1  0  0  0  0
  2 17  1  1  0  0  0
  3 18  1  1  0  0  0
 21 22  1  0  0  0  0
 21 25  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 26 28  1  0  0  0  0
 28 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 28 29  1  6  0  0  0
 26 34  1  6  0  0  0
 26 27  1  1  0  0  0
 32 36  1  0  0  0  0
 21 26  1  0  0  0  0
 21 35  1  6  0  0  0
 12 22  1  0  0  0  0
 22 13  1  1  0  0  0
 23 19  1  6  0  0  0
  8 23  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0052170

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@@]1(CC[C@@]2(O)C3=CC(=O)[C@]4([H])C[C@@H](O)[C@@H](O)C[C@]4(C)[C@@]3([H])CC[C@]12C)[C@@](C)(O)[C@H](O)CCC(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C27H44O6/c1-15(2)6-7-23(31)26(5,32)22-9-11-27(33)17-12-19(28)18-13-20(29)21(30)14-24(18,3)16(17)8-10-25(22,27)4/h12,15-16,18,20-23,29-33H,6-11,13-14H2,1-5H3/t16-,18-,20+,21-,22-,23+,24+,25+,26+,27+/m0/s1

> <INCHI_KEY>
PJYYBCXMCWDUAZ-JJJZTNILSA-N

> <FORMULA>
C27H44O6

> <MOLECULAR_WEIGHT>
464.6347

> <EXACT_MASS>
464.31378914

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
77

> <JCHEM_AVERAGE_POLARIZABILITY>
52.82996351154999

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,2R,4S,5R,7R,11S,14S,15R)-14-[(2R,3R)-2,3-dihydroxy-6-methylheptan-2-yl]-4,5,11-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-9-en-8-one

> <ALOGPS_LOGP>
2.14

> <JCHEM_LOGP>
2.080976889666665

> <ALOGPS_LOGS>
-3.31

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.743303424775707

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.261564175718128

> <JCHEM_PKA_STRONGEST_BASIC>
-3.153288443303487

> <JCHEM_POLAR_SURFACE_AREA>
118.22000000000001

> <JCHEM_REFRACTIVITY>
127.03969999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.28e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2R,4S,5R,7R,11S,14S,15R)-14-[(2R,3R)-2,3-dihydroxy-6-methylheptan-2-yl]-4,5,11-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-9-en-8-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 27-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-SEP-20         0                                  
HETATM    1  C   UNK     0      11.793 -11.297   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      10.408 -12.072   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      10.408 -13.624   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      11.793 -14.400   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      13.178 -13.624   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      14.508 -14.400   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      15.893 -13.624   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      15.893 -12.017   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      14.508 -11.297   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      13.178 -12.072   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      14.508  -9.690   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      15.893  -8.914   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      17.223  -8.139   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      13.178 -10.521   0.000  0.00  0.00           C+0
HETATM   15  H   UNK     0      14.508 -12.903   0.000  0.00  0.00           H+0
HETATM   16  O   UNK     0      14.508 -16.006   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       9.023 -11.241   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       9.023 -14.455   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      17.223 -12.903   0.000  0.00  0.00           O+0
HETATM   20  H   UNK     0      13.178 -15.230   0.000  0.00  0.00           H+0
HETATM   21  C   UNK     0      18.687  -9.247   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      17.223  -9.723   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      17.223 -11.263   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      18.687 -11.739   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      19.592 -10.493   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      18.687  -7.708   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      17.354  -6.938   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      20.021  -6.938   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      20.021  -5.398   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      21.354  -7.708   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      22.688  -6.938   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      24.021  -7.708   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      25.354  -6.938   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      18.687  -6.168   0.000  0.00  0.00           C+0
HETATM   35  H   UNK     0      20.021  -8.478   0.000  0.00  0.00           H+0
HETATM   36  C   UNK     0      24.021  -9.201   0.000  0.00  0.00           C+0
CONECT    1   10    2                                                       
CONECT    2    1    3   17                                                  
CONECT    3    4    2   18                                                  
CONECT    4    5    3                                                       
CONECT    5   10    4    6   20                                             
CONECT    6    7    5   16                                                  
CONECT    7    8    6                                                       
CONECT    8    9    7   23                                                  
CONECT    9   10    8   15   11                                             
CONECT   10    9    5   14    1                                             
CONECT   11    9   12                                                       
CONECT   12   11   22                                                       
CONECT   13   22                                                            
CONECT   14   10                                                            
CONECT   15    9                                                            
CONECT   16    6                                                            
CONECT   17    2                                                            
CONECT   18    3                                                            
CONECT   19   23                                                            
CONECT   20    5                                                            
CONECT   21   22   25   26   35                                             
CONECT   22   21   23   12   13                                             
CONECT   23   22   24   19    8                                             
CONECT   24   23   25                                                       
CONECT   25   21   24                                                       
CONECT   26   28   34   27   21                                             
CONECT   27   26                                                            
CONECT   28   26   30   29                                                  
CONECT   29   28                                                            
CONECT   30   28   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   33   36                                                  
CONECT   33   32                                                            
CONECT   34   26                                                            
CONECT   35   21                                                            
CONECT   36   32                                                            
MASTER        0    0    0    0    0    0    0    0   36    0   78    0
END

View in JSmol

Synonyms

Value	Source
25-Deoxycedysterone	ChEBI
25-Deoxy-20-ecdysone	MeSH
2 beta,3 beta,14,20,22-Pentahydroxy-5 beta- cholest-7-en-6-one	MeSH
Ponasterone a, ponasterone b (2alpha,3alpha,5beta,22R)-isomer	MeSH
25-Deoxyecdysterone	MeSH
(2beta,3beta,5beta,22R)-2,3,14,20,22-Pentahydroxycholest-7-en-6-one	PhytoBank
(2β,3β,5β,22R)-2,3,14,20,22-Pentahydroxycholest-7-en-6-one	PhytoBank

Chemical Formula

C₂₇H₄₄O₆

Average Mass

464.6347 Da

Monoisotopic Mass

464.31379 Da

IUPAC Name

(1R,2R,4S,5R,7R,11S,14S,15R)-14-[(2R,3R)-2,3-dihydroxy-6-methylheptan-2-yl]-4,5,11-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-9-en-8-one

Traditional Name

(1R,2R,4S,5R,7R,11S,14S,15R)-14-[(2R,3R)-2,3-dihydroxy-6-methylheptan-2-yl]-4,5,11-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-9-en-8-one

CAS Registry Number

Not Available

SMILES

[H][C@@]1(CC[C@@]2(O)C3=CC(=O)[C@]4([H])C[C@@H](O)[C@@H](O)C[C@]4(C)[C@@]3([H])CC[C@]12C)[C@@](C)(O)[C@H](O)CCC(C)C

InChI Identifier

InChI=1S/C27H44O6/c1-15(2)6-7-23(31)26(5,32)22-9-11-27(33)17-12-19(28)18-13-20(29)21(30)14-24(18,3)16(17)8-10-25(22,27)4/h12,15-16,18,20-23,29-33H,6-11,13-14H2,1-5H3/t16-,18-,20+,21-,22-,23+,24+,25+,26+,27+/m0/s1

InChI Key

PJYYBCXMCWDUAZ-JJJZTNILSA-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
Afrocarpus gracilior	LOTUS Database	35616633
Bolbitis subcordata	Plant	KNApSAcK
Brainea insignis	LOTUS Database	35616633
Iotrochota birotulata	LOTUS Database	35616633
Limnanthes douglasii	LOTUS Database	35616633
Matteuccia struthiopteris	Plant	KNApSAcK
Osmunda japonica	Plant	KNApSAcK
Plenasium banksiaefolium	-	KNApSAcK
Plenasium banksiifolium	LOTUS Database	35616633
Podocarpus macrophyllus	Plant	KNApSAcK
Podocarpus macrophyllus var.maki	Plant	KNApSAcK
Podocarpus nakaii	Plant	KNApSAcK
Pteridium aquilinum	LOTUS Database	35616633
Pteridium aquilinum var.latiusculum	Plant	KNApSAcK
Tapinella panuoides	Fungi	KNApSAcK
Taxus brevifolia	Plant	KNApSAcK
Taxus cuspidata	Plant	KNApSAcK
Taxus floridana	LOTUS Database	35616633
Taxus mairei	LOTUS Database	35616633
Taxus wallichiana	LOTUS Database	35616633
Woodwardia orientalis	Plant	KNApSAcK
Zoanthus sp.	Animalia	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pentahydroxy bile acids, alcohols and derivatives. These are bile acids, alcohols or derivatives bearing five hydroxyl groups.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Bile acids, alcohols and derivatives

Direct Parent

Pentahydroxy bile acids, alcohols and derivatives

Alternative Parents

Substituents

Pentahydroxy bile acid, alcohol, or derivatives
Cholesterol-skeleton
Cholesterol
Cholestane-skeleton
Ecdysteroid
22-hydroxysteroid
20-hydroxysteroid
2-hydroxysteroid
6-oxosteroid
3-beta-hydroxysteroid
Hydroxysteroid
14-hydroxysteroid
Oxosteroid
3-hydroxysteroid
3-hydroxy-delta-7-steroid
Delta-7-steroid
Cyclohexenone
Tertiary alcohol
Cyclic alcohol
Secondary alcohol
Ketone
Polyol
Organic oxide
Organic oxygen compound
Hydrocarbon derivative
Carbonyl group
Alcohol
Organooxygen compound
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

3beta-hydroxy steroid (CHEBI:28135 )
20-hydroxy steroid (CHEBI:28135 )
6-oxo steroid (CHEBI:28135 )
22-hydroxy steroid (CHEBI:28135 )
2beta-hydroxy steroid (CHEBI:28135 )
14alpha-hydroxy steroid (CHEBI:28135 )
phytoecdysteroid (CHEBI:28135 )
cholestane (C08835 )
Cholesterol and derivatives (LMST01010195 )

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	2.14	ALOGPS
logP	2.08	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Acidic)	13.26	ChemAxon
pKa (Strongest Basic)	-3.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	118.22 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	127.04 m³·mol⁻¹	ChemAxon
Polarizability	52.83 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	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

C00003667

Chemspider ID

Not Available

KEGG Compound ID

C08835

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

115127

PDB ID

Not Available

ChEBI ID

28135

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Ponasterone A (NP0052170)

MOL for NP0052170 (Ponasterone A)

3D MOL for NP0052170 (Ponasterone A)

3D SDF for NP0052170 (Ponasterone A)

3D-SDF for NP0052170 (Ponasterone A)

PDB for NP0052170 (Ponasterone A)

3D PDB for NP0052170 (Ponasterone A)

SMILES for NP0052170 (Ponasterone A)

INCHI for NP0052170 (Ponasterone A)

Structure for NP0052170 (Ponasterone A)

3D Structure for NP0052170 (Ponasterone A)