NP-MRD: Showing NP-Card for 12-O-benzoyldeacylmetaplexigenin (NP0071896)

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Record Information

Version

2.0

Created at

2022-04-28 17:16:42 UTC

Updated at

2022-04-28 17:16:43 UTC

NP-MRD ID

NP0071896

Secondary Accession Numbers

None

Natural Product Identification

Common Name

12-O-benzoyldeacylmetaplexigenin

Description

19308-44-2 Belongs to the class of organic compounds known as gluco/mineralocorticoids, progestogins and derivatives. These are steroids with a structure based on a hydroxylated prostane moiety. 12-O-benzoyldeacylmetaplexigenin is found in Araujia sericifera. Based on a literature review very few articles have been published on 19308-44-2.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282219162D          

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M  END

     RDKit          3D

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  Mrv1652304282219162D          

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M  END
> <DATABASE_ID>
NP0071896

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)[C@]1(O)CC[C@@]2(O)[C@]1(C)[C@@H](C[C@@H]1[C@@]3(C)CC[C@H](O)CC3=CC[C@@]21O)OC(=O)C1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C28H36O7/c1-17(29)26(32)13-14-28(34)25(26,3)22(35-23(31)18-7-5-4-6-8-18)16-21-24(2)11-10-20(30)15-19(24)9-12-27(21,28)33/h4-9,20-22,30,32-34H,10-16H2,1-3H3/t20-,21+,22+,24-,25+,26+,27-,28+/m0/s1

> <INCHI_KEY>
XESLPBJMIWFAMZ-ZCARJHNXSA-N

> <FORMULA>
C28H36O7

> <MOLECULAR_WEIGHT>
484.589

> <EXACT_MASS>
484.246103499

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
71

> <JCHEM_AVERAGE_POLARIZABILITY>
51.41789180223191

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,2R,5S,10S,11R,14S,15S,16R)-14-acetyl-5,10,11,14-tetrahydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-16-yl benzoate

> <ALOGPS_LOGP>
1.81

> <JCHEM_LOGP>
2.0136837713333335

> <ALOGPS_LOGS>
-3.62

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.149980421893368

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.392590222488664

> <JCHEM_PKA_STRONGEST_BASIC>
-1.3972428675356348

> <JCHEM_POLAR_SURFACE_AREA>
124.29000000000002

> <JCHEM_REFRACTIVITY>
129.3194

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.17e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2R,5S,10S,11R,14S,15S,16R)-14-acetyl-5,10,11,14-tetrahydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-16-yl 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      11.519  -0.407   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      12.042   1.041   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      11.049   2.218   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.533   1.947   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.541   3.125   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.025   2.854   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.502   1.405   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.494   0.228   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.010   0.499   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      10.003  -0.678   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.487  -0.949   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.971  -1.221   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.455  -1.492   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.462  -0.314   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.986   1.134   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.770   2.079   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.495   1.215   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.923  -0.264   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       2.697  -1.787   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       1.503  -0.859   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       0.277   0.073   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       1.308  -2.387   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       5.355   2.629   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       3.791  -1.700   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       4.932  -2.940   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       5.925  -4.117   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       5.401  -5.566   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       7.441  -3.846   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       7.964  -2.398   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       9.480  -2.127   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      10.472  -3.304   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       9.949  -4.752   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       8.433  -5.024   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       5.921   2.832   0.000  0.00  0.00           O+0
HETATM   35  O   UNK     0      13.558   1.312   0.000  0.00  0.00           O+0
CONECT    1    2   10                                                       
CONECT    2    1    3   35                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    9                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8   15   34                                             
CONECT    8    7    9   12                                                  
CONECT    9    8    4   10   11                                             
CONECT   10    9    1                                                       
CONECT   11    9                                                            
CONECT   12    8   13                                                       
CONECT   13   12   14   25                                                  
CONECT   14   13   15   18   24                                             
CONECT   15   14    7   16   23                                             
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   14   19   20                                             
CONECT   19   18                                                            
CONECT   20   18   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20                                                            
CONECT   23   15                                                            
CONECT   24   14                                                            
CONECT   25   13   26                                                       
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   29   33                                                  
CONECT   29   28   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   28                                                       
CONECT   34    7                                                            
CONECT   35    2                                                            
MASTER        0    0    0    0    0    0    0    0   35    0   78    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₈H₃₆O₇

Average Mass

484.5890 Da

Monoisotopic Mass

484.24610 Da

IUPAC Name

(1R,2R,5S,10S,11R,14S,15S,16R)-14-acetyl-5,10,11,14-tetrahydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-16-yl benzoate

Traditional Name

(1R,2R,5S,10S,11R,14S,15S,16R)-14-acetyl-5,10,11,14-tetrahydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-16-yl benzoate

CAS Registry Number

Not Available

SMILES

CC(=O)[C@]1(O)CC[C@@]2(O)[C@]1(C)[C@@H](C[C@@H]1[C@@]3(C)CC[C@H](O)CC3=CC[C@@]21O)OC(=O)C1=CC=CC=C1

InChI Identifier

InChI=1S/C28H36O7/c1-17(29)26(32)13-14-28(34)25(26,3)22(35-23(31)18-7-5-4-6-8-18)16-21-24(2)11-10-20(30)15-19(24)9-12-27(21,28)33/h4-9,20-22,30,32-34H,10-16H2,1-3H3/t20-,21+,22+,24-,25+,26+,27-,28+/m0/s1

InChI Key

XESLPBJMIWFAMZ-ZCARJHNXSA-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
Araujia sericifera	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as gluco/mineralocorticoids, progestogins and derivatives. These are steroids with a structure based on a hydroxylated prostane moiety.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Pregnane steroids

Direct Parent

Gluco/mineralocorticoids, progestogins and derivatives

Alternative Parents

Substituents

Progestogin-skeleton
20-oxosteroid
3-hydroxy-delta-5-steroid
3-hydroxysteroid
17-hydroxysteroid
3-beta-hydroxysteroid
3-beta-hydroxy-delta-5-steroid
14-hydroxysteroid
Oxosteroid
Hydroxysteroid
Delta-5-steroid
Benzoate ester
Benzoic acid or derivatives
Benzoyl
Monocyclic benzene moiety
Benzenoid
Tertiary alcohol
Cyclic alcohol
Alpha-hydroxy ketone
Ketone
Secondary alcohol
Carboxylic acid ester
Monocarboxylic acid or derivatives
Polyol
Carboxylic acid derivative
Organooxygen compound
Hydrocarbon derivative
Organic oxygen compound
Carbonyl group
Alcohol
Organic oxide
Aromatic homopolycyclic compound

Molecular Framework

Aromatic 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	1.81	ALOGPS
logP	2.01	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Acidic)	12.39	ChemAxon
pKa (Strongest Basic)	-1.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	124.29 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	129.32 m³·mol⁻¹	ChemAxon
Polarizability	51.42 Å³	ChemAxon
Number of Rings	5	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

C00031497

Chemspider ID

8430250

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10254765

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for 12-O-benzoyldeacylmetaplexigenin (NP0071896)

MOL for NP0071896 (12-O-benzoyldeacylmetaplexigenin)

3D MOL for NP0071896 (12-O-benzoyldeacylmetaplexigenin)

3D SDF for NP0071896 (12-O-benzoyldeacylmetaplexigenin)

3D-SDF for NP0071896 (12-O-benzoyldeacylmetaplexigenin)

PDB for NP0071896 (12-O-benzoyldeacylmetaplexigenin)

3D PDB for NP0071896 (12-O-benzoyldeacylmetaplexigenin)

SMILES for NP0071896 (12-O-benzoyldeacylmetaplexigenin)

INCHI for NP0071896 (12-O-benzoyldeacylmetaplexigenin)

Structure for NP0071896 (12-O-benzoyldeacylmetaplexigenin)

3D Structure for NP0071896 (12-O-benzoyldeacylmetaplexigenin)