NP-MRD: Showing NP-Card for (+)-Viticosterone E (NP0080325)

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Record Information

Version

2.0

Created at

2022-04-29 01:21:40 UTC

Updated at

2022-04-29 01:21:40 UTC

NP-MRD ID

NP0080325

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(+)-Viticosterone E

Description

Viticosterone E 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. (+)-Viticosterone E is found in Ajuga reptans, Digitalis purpurea, Klasea sogdiana, Rhaponticum integrifolium, Serratula coronata, Silene brahuica, Silene chalcedonica, Silene linicola, Silene wallichiana, Vitex agnus-castus, Vitex megapotamica and Zoanthus sp.. (+)-Viticosterone E was first documented in 2002 (PMID: 12193031). Based on a literature review very few articles have been published on Viticosterone E (PMID: 34302431).

Structure

MOL 3D MOL SDF PDB SMILES InChI

  Mrv1652304292203212D          

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M  END

     RDKit          3D

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M  END

  Mrv1652304292203212D          

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   -1.0592    4.1438    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5151    2.2220    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2124    3.2347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1073    2.8462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9451    0.5269    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6232    2.4441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3399    1.2325    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7793    2.7844    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
  4  3  1  1  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  1  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  6  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
  4 10  1  0  0  0  0
 10 11  2  0  0  0  0
  8 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
  7 15  1  0  0  0  0
 13 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 12 18  1  0  0  0  0
 16 19  1  6  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 23 25  1  0  0  0  0
 23 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 27 29  1  0  0  0  0
 20 30  1  1  0  0  0
 19 31  1  6  0  0  0
 19 32  1  6  0  0  0
 13 33  1  6  0  0  0
 12 34  1  1  0  0  0
  5 35  1  6  0  0  0
  2 36  1  6  0  0  0
  1 37  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0080325

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C29H46O8/c1-16(30)37-25(2,3)10-9-24(34)28(6,35)23-8-12-29(36)18-13-20(31)19-14-21(32)22(33)15-26(19,4)17(18)7-11-27(23,29)5/h13,17,19,21-24,32-36H,7-12,14-15H2,1-6H3/t17-,19-,21+,22-,23-,24+,26+,27+,28+,29+/m0/s1

> <INCHI_KEY>
DWHBRFSKXQCVDN-FORVDKSSSA-N

> <FORMULA>
C29H46O8

> <MOLECULAR_WEIGHT>
522.679

> <EXACT_MASS>
522.319268441

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
83

> <JCHEM_AVERAGE_POLARIZABILITY>
57.812549701662846

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(5R,6R)-5,6-dihydroxy-2-methyl-6-[(1R,2R,4S,5R,7R,11S,14S,15R)-4,5,11-trihydroxy-2,15-dimethyl-8-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-9-en-14-yl]heptan-2-yl acetate

> <ALOGPS_LOGP>
1.89

> <JCHEM_LOGP>
1.0509876150000013

> <ALOGPS_LOGS>
-3.60

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.742606839920164

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.260670992937158

> <JCHEM_PKA_STRONGEST_BASIC>
-3.153288443303487

> <JCHEM_POLAR_SURFACE_AREA>
144.52

> <JCHEM_REFRACTIVITY>
138.02730000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.30e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(5R,6R)-5,6-dihydroxy-2-methyl-6-[(1R,2R,4S,5R,7R,11S,14S,15R)-4,5,11-trihydroxy-2,15-dimethyl-8-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-9-en-14-yl]heptan-2-yl acetate

> <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       7.929   4.020   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.452   2.572   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.459   1.394   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.943   1.666   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.420   3.114   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.413   4.291   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.904   3.385   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.911   2.208   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.434   0.759   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.950   0.488   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       5.474  -0.960   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       1.395   2.479   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.872   3.927   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.865   5.104   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.381   4.833   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -0.667   3.877   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -1.095   2.398   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.179   1.534   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -1.612   5.093   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -2.557   6.309   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -4.083   6.098   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -5.028   7.314   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -6.554   7.103   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -6.343   5.578   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -6.764   8.629   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      -8.079   6.893   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      -9.024   8.108   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0     -10.550   7.898   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      -8.444   9.535   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      -1.977   7.735   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0      -2.828   4.148   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      -0.396   6.038   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       0.200   5.313   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       1.764   0.984   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0       4.897   4.562   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0       9.968   2.301   0.000  0.00  0.00           O+0
HETATM   37  O   UNK     0       8.921   5.197   0.000  0.00  0.00           O+0
CONECT    1    2    6   37                                                  
CONECT    2    1    3   36                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   10                                                  
CONECT    5    4    6    7   35                                             
CONECT    6    5    1                                                       
CONECT    7    5    8   15                                                  
CONECT    8    7    9   12                                                  
CONECT    9    8   10                                                       
CONECT   10    9    4   11                                                  
CONECT   11   10                                                            
CONECT   12    8   13   18   34                                             
CONECT   13   12   14   16   33                                             
CONECT   14   13   15                                                       
CONECT   15   14    7                                                       
CONECT   16   13   17   19                                                  
CONECT   17   16   18                                                       
CONECT   18   17   12                                                       
CONECT   19   16   20   31   32                                             
CONECT   20   19   21   30                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24   25   26                                             
CONECT   24   23                                                            
CONECT   25   23                                                            
CONECT   26   23   27                                                       
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27                                                            
CONECT   30   20                                                            
CONECT   31   19                                                            
CONECT   32   19                                                            
CONECT   33   13                                                            
CONECT   34   12                                                            
CONECT   35    5                                                            
CONECT   36    2                                                            
CONECT   37    1                                                            
MASTER        0    0    0    0    0    0    0    0   37    0   80    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₉H₄₆O₈

Average Mass

522.6790 Da

Monoisotopic Mass

522.31927 Da

IUPAC Name

(5R,6R)-5,6-dihydroxy-2-methyl-6-[(1R,2R,4S,5R,7R,11S,14S,15R)-4,5,11-trihydroxy-2,15-dimethyl-8-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-9-en-14-yl]heptan-2-yl acetate

Traditional Name

(5R,6R)-5,6-dihydroxy-2-methyl-6-[(1R,2R,4S,5R,7R,11S,14S,15R)-4,5,11-trihydroxy-2,15-dimethyl-8-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-9-en-14-yl]heptan-2-yl acetate

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C29H46O8/c1-16(30)37-25(2,3)10-9-24(34)28(6,35)23-8-12-29(36)18-13-20(31)19-14-21(32)22(33)15-26(19,4)17(18)7-11-27(23,29)5/h13,17,19,21-24,32-36H,7-12,14-15H2,1-6H3/t17-,19-,21+,22-,23-,24+,26+,27+,28+,29+/m0/s1

InChI Key

DWHBRFSKXQCVDN-FORVDKSSSA-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
Ajuga reptans	LOTUS Database	35616633
Digitalis purpurea	LOTUS Database	35616633
Klasea sogdiana	LOTUS Database	35616633
Rhaponticum integrifolium	LOTUS Database	35616633
Serratula coronata	LOTUS Database	35616633
Silene brahuica	LOTUS Database	35616633
Silene chalcedonica	LOTUS Database	35616633
Silene linicola	LOTUS Database	35616633
Silene wallichiana	LOTUS Database	35616633
Vitex agnus-castus	LOTUS Database	35616633
Vitex megapotamica	LOTUS Database	35616633
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
Steroid ester
20-hydroxysteroid
2-hydroxysteroid
6-oxosteroid
3-beta-hydroxysteroid
14-hydroxysteroid
Hydroxysteroid
Oxosteroid
3-hydroxysteroid
3-hydroxy-delta-7-steroid
Delta-7-steroid
Cyclohexenone
Tertiary alcohol
Cyclic alcohol
Secondary alcohol
Carboxylic acid ester
Ketone
Polyol
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Organooxygen compound
Organic oxide
Organic oxygen compound
Hydrocarbon derivative
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	1.89	ALOGPS
logP	1.05	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Acidic)	13.26	ChemAxon
pKa (Strongest Basic)	-3.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	144.52 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	138.03 m³·mol⁻¹	ChemAxon
Polarizability	57.81 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00045448

Chemspider ID

9401264

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11226211

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Suksamrarn A, Jankam A, Tarnchompoo B, Putchakarn S: Ecdysteroids from a Zoanthus sp. J Nat Prod. 2002 Aug;65(8):1194-7. doi: 10.1021/np010645s. [PubMed:12193031 ]
Jiang P, Liu Y, Sun YP, Pan J, Guan W, Xu ZP, Li XM, Wang SY, Mei Y, Kuang HX, Yang BY: Ecdysteroids from the Aerial Parts of Paris verticillata. Chem Biodivers. 2021 Sep;18(9):e2100239. doi: 10.1002/cbdv.202100239. Epub 2021 Aug 9. [PubMed:34302431 ]

Showing NP-Card for (+)-Viticosterone E (NP0080325)

MOL for NP0080325 ((+)-Viticosterone E)

3D MOL for NP0080325 ((+)-Viticosterone E)

3D SDF for NP0080325 ((+)-Viticosterone E)

3D-SDF for NP0080325 ((+)-Viticosterone E)

PDB for NP0080325 ((+)-Viticosterone E)

3D PDB for NP0080325 ((+)-Viticosterone E)

SMILES for NP0080325 ((+)-Viticosterone E)

INCHI for NP0080325 ((+)-Viticosterone E)

Structure for NP0080325 ((+)-Viticosterone E)

3D Structure for NP0080325 ((+)-Viticosterone E)