NP-MRD: Showing NP-Card for (+)-Argenteanol E (NP0083008)

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Record Information

Version

2.0

Created at

2022-04-29 04:03:58 UTC

Updated at

2022-04-29 04:03:58 UTC

NP-MRD ID

NP0083008

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(+)-Argenteanol E

Description

(1S,3R,6S,7S,8S,11S,12S,15R,16R)-15-[(2R,4R,5R)-5-hydroperoxy-4-hydroxy-6-methylhept-6-en-2-yl]-7,12,16-trimethylpentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]Octadecan-6-ol belongs to the class of organic compounds known as cycloartanols and derivatives. These are steroids containing a cycloartanol moiety. (+)-Argenteanol E is found in Aglaia argentea . Based on a literature review very few articles have been published on (1S,3R,6S,7S,8S,11S,12S,15R,16R)-15-[(2R,4R,5R)-5-hydroperoxy-4-hydroxy-6-methylhept-6-en-2-yl]-7,12,16-trimethylpentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]Octadecan-6-ol.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304292206042D          

 33 37  0  0  1  0            999 V2000
    4.0480    1.4789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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 26 33  1  1  0  0  0
  2 33  1  1  0  0  0
M  END

     RDKit          3D

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M  END


  Mrv1652304292206042D          

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  8  9  1  0  0  0  0
  4  9  1  0  0  0  0
  7 10  1  1  0  0  0
 10 11  1  6  0  0  0
 10 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
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
 14 18  1  1  0  0  0
 18 19  1  0  0  0  0
 13 20  1  1  0  0  0
  5 21  1  1  0  0  0
  4 22  1  6  0  0  0
  3 23  1  6  0  0  0
 23 24  1  0  0  0  0
 25 24  1  1  0  0  0
 25 26  1  0  0  0  0
  2 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 25 30  1  0  0  0  0
 30 31  1  6  0  0  0
 29 32  1  1  0  0  0
 26 33  1  1  0  0  0
  2 33  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0083008

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@H](C[C@@H](O)[C@H](OO)C(C)=C)[C@H]1CC[C@@]2(C)[C@@H]3CC[C@H]4[C@H](C)[C@@H](O)CC[C@@]44C[C@@]34CC[C@]12C

> <INCHI_IDENTIFIER>
InChI=1S/C29H48O4/c1-17(2)25(33-32)23(31)15-18(3)20-9-11-27(6)24-8-7-21-19(4)22(30)10-12-28(21)16-29(24,28)14-13-26(20,27)5/h18-25,30-32H,1,7-16H2,2-6H3/t18-,19+,20-,21+,22+,23-,24+,25-,26-,27+,28-,29+/m1/s1

> <INCHI_KEY>
BEXKXFSUDVVSFA-ZLOFJMPJSA-N

> <FORMULA>
C29H48O4

> <MOLECULAR_WEIGHT>
460.699

> <EXACT_MASS>
460.355260026

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
81

> <JCHEM_AVERAGE_POLARIZABILITY>
55.42637577150959

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,3R,6S,7S,8S,11S,12S,15R,16R)-15-[(2R,4R,5R)-5-hydroperoxy-4-hydroxy-6-methylhept-6-en-2-yl]-7,12,16-trimethylpentacyclo[9.7.0.0^{1,3}.0^{3,8}.0^{12,16}]octadecan-6-ol

> <ALOGPS_LOGP>
4.54

> <JCHEM_LOGP>
5.371215903

> <ALOGPS_LOGS>
-5.31

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.467056589166397

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.69836170719914

> <JCHEM_PKA_STRONGEST_BASIC>
-1.0961423788057658

> <JCHEM_POLAR_SURFACE_AREA>
69.92

> <JCHEM_REFRACTIVITY>
130.78979999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.28e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,3R,6S,7S,8S,11S,12S,15R,16R)-15-[(2R,4R,5R)-5-hydroperoxy-4-hydroxy-6-methylhept-6-en-2-yl]-7,12,16-trimethylpentacyclo[9.7.0.0^{1,3}.0^{3,8}.0^{12,16}]octadecan-6-ol

> <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       7.556   2.761   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       7.033   1.312   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.026   0.135   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.542   0.406   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      10.065   1.854   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.072   3.032   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      11.604   1.804   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      12.032   0.325   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      10.757  -0.539   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      12.549   3.020   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      11.969   4.447   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      14.075   2.809   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      15.020   4.025   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      16.545   3.815   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      17.491   5.030   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      19.016   4.820   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      16.910   6.457   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      17.126   2.388   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      16.181   1.172   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      14.440   5.452   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      10.737   3.240   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       9.173  -1.089   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       7.502  -1.314   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       5.986  -1.585   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       4.994  -0.407   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       5.517   1.041   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       4.524   2.218   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       3.008   1.947   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       2.485   0.499   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       3.478  -0.678   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       2.955  -2.127   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       0.969   0.228   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       6.040   2.489   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    3   26   33                                             
CONECT    3    2    4   23                                                  
CONECT    4    3    5    9   22                                             
CONECT    5    4    6    7   21                                             
CONECT    6    5    1                                                       
CONECT    7    5    8   10                                                  
CONECT    8    7    9                                                       
CONECT    9    8    4                                                       
CONECT   10    7   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12   14   20                                                  
CONECT   14   13   15   18                                                  
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15                                                            
CONECT   18   14   19                                                       
CONECT   19   18                                                            
CONECT   20   13                                                            
CONECT   21    5                                                            
CONECT   22    4                                                            
CONECT   23    3   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26   30                                                  
CONECT   26   25    2   27   33                                             
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30   32                                                  
CONECT   30   29   25   31                                                  
CONECT   31   30                                                            
CONECT   32   29                                                            
CONECT   33   26    2                                                       
MASTER        0    0    0    0    0    0    0    0   33    0   74    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₉H₄₈O₄

Average Mass

460.6990 Da

Monoisotopic Mass

460.35526 Da

IUPAC Name

(1S,3R,6S,7S,8S,11S,12S,15R,16R)-15-[(2R,4R,5R)-5-hydroperoxy-4-hydroxy-6-methylhept-6-en-2-yl]-7,12,16-trimethylpentacyclo[9.7.0.0^{1,3}.0^{3,8}.0^{12,16}]octadecan-6-ol

Traditional Name

(1S,3R,6S,7S,8S,11S,12S,15R,16R)-15-[(2R,4R,5R)-5-hydroperoxy-4-hydroxy-6-methylhept-6-en-2-yl]-7,12,16-trimethylpentacyclo[9.7.0.0^{1,3}.0^{3,8}.0^{12,16}]octadecan-6-ol

CAS Registry Number

Not Available

SMILES

C[C@H](C[C@@H](O)[C@H](OO)C(C)=C)[C@H]1CC[C@@]2(C)[C@@H]3CC[C@H]4[C@H](C)[C@@H](O)CC[C@@]44C[C@@]34CC[C@]12C

InChI Identifier

InChI=1S/C29H48O4/c1-17(2)25(33-32)23(31)15-18(3)20-9-11-27(6)24-8-7-21-19(4)22(30)10-12-28(21)16-29(24,28)14-13-26(20,27)5/h18-25,30-32H,1,7-16H2,2-6H3/t18-,19+,20-,21+,22+,23-,24+,25-,26-,27+,28-,29+/m1/s1

InChI Key

BEXKXFSUDVVSFA-ZLOFJMPJSA-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
Aglaia argentea	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cycloartanols and derivatives. These are steroids containing a cycloartanol moiety.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Cycloartanols and derivatives

Direct Parent

Cycloartanols and derivatives

Alternative Parents

Substituents

Cycloartanol-skeleton
Triterpenoid
Cycloartane-skeleton
9b,19-cyclo-lanostane-skeleton
Dihydroxy bile acid, alcohol, or derivatives
23-hydroxysteroid
Hydroxy bile acid, alcohol, or derivatives
Bile acid, alcohol, or derivatives
3-beta-hydroxysteroid
Hydroxysteroid
3-hydroxysteroid
Cyclic alcohol
Secondary alcohol
Hydroperoxide
Alkyl hydroperoxide
Peroxol
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
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	4.54	ALOGPS
logP	5.37	ChemAxon
logS	-5.3	ALOGPS
pKa (Strongest Acidic)	11.7	ChemAxon
pKa (Strongest Basic)	-1.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	69.92 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	130.79 m³·mol⁻¹	ChemAxon
Polarizability	55.43 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	Yes	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

8751344

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10575958

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for (+)-Argenteanol E (NP0083008)

MOL for NP0083008 ((+)-Argenteanol E)

3D MOL for NP0083008 ((+)-Argenteanol E)

3D SDF for NP0083008 ((+)-Argenteanol E)

3D-SDF for NP0083008 ((+)-Argenteanol E)

PDB for NP0083008 ((+)-Argenteanol E)

3D PDB for NP0083008 ((+)-Argenteanol E)

SMILES for NP0083008 ((+)-Argenteanol E)

INCHI for NP0083008 ((+)-Argenteanol E)

Structure for NP0083008 ((+)-Argenteanol E)

3D Structure for NP0083008 ((+)-Argenteanol E)