NP-MRD: Showing NP-Card for (+)-Argenteanol C (NP0083006)

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Record Information

Version

2.0

Created at

2022-04-29 04:03:53 UTC

Updated at

2022-04-29 04:03:53 UTC

NP-MRD ID

NP0083006

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(+)-Argenteanol C

Description

Argenteanol C belongs to the class of organic compounds known as limonoids. These are highly oxygenated, modified terpenoids with a prototypical structure either containing or derived from a precursor with a 4,4,8-trimethyl-17-furanylsteroid skeleton. All naturally occurring citrus limonoids contain a furan ring attached to the D-ring, at C-17, as well as oxygen containing functional groups at C-3, C-4, C-7, C-16 and C-17. (+)-Argenteanol C is found in Aglaia argentea . Based on a literature review very few articles have been published on Argenteanol C.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304292206032D          

 34 39  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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M  END

     RDKit          3D

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M  END


  Mrv1652304292206032D          

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  1  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  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
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 10 14  1  0  0  0  0
 14 15  1  1  0  0  0
 13 16  1  1  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 11 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  0  0  0  0
 30 32  1  0  0  0  0
 29 33  1  1  0  0  0
 26 34  1  1  0  0  0
  2 34  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0083006

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)=C[C@@H]1O[C@H](O)[C@H]([C@@H]1O)[C@H]1CC[C@@]2(C)[C@@H]3CC[C@@H]4[C@]5(C[C@@]35CC[C@]12C)CC[C@H](O)C4(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C30H48O4/c1-17(2)15-19-24(32)23(25(33)34-19)18-9-11-28(6)21-8-7-20-26(3,4)22(31)10-12-29(20)16-30(21,29)14-13-27(18,28)5/h15,18-25,31-33H,7-14,16H2,1-6H3/t18-,19+,20+,21+,22+,23+,24-,25+,27-,28+,29-,30+/m1/s1

> <INCHI_KEY>
WZYISXKEYZUNQE-LBXJHVLXSA-N

> <FORMULA>
C30H48O4

> <MOLECULAR_WEIGHT>
472.71

> <EXACT_MASS>
472.355260026

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
82

> <JCHEM_AVERAGE_POLARIZABILITY>
56.41659509885313

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
4.12

> <JCHEM_LOGP>
4.827430867333335

> <ALOGPS_LOGS>
-4.78

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.840007871022848

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.064389978812104

> <JCHEM_PKA_STRONGEST_BASIC>
-0.835010315980412

> <JCHEM_POLAR_SURFACE_AREA>
69.92

> <JCHEM_REFRACTIVITY>
133.97609999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.78e-03 g/l

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

> <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      12.121   4.499   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      13.396   5.364   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      14.612   4.418   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      14.088   2.970   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      14.953   1.695   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      16.091   4.846   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      17.201   3.779   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      18.681   4.207   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      16.832   2.284   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      10.673   5.023   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       2.336  -1.712   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       3.696  -2.203   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       0.969   0.228   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       6.040   2.489   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    3   26   34                                             
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   14                                                  
CONECT   11   10   12   20                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   16                                                  
CONECT   14   13   10   15                                                  
CONECT   15   14                                                            
CONECT   16   13   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17                                                            
CONECT   20   11                                                            
CONECT   21    5                                                            
CONECT   22    4                                                            
CONECT   23    3   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26   30                                                  
CONECT   26   25    2   27   34                                             
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30   33                                                  
CONECT   30   29   25   31   32                                             
CONECT   31   30                                                            
CONECT   32   30                                                            
CONECT   33   29                                                            
CONECT   34   26    2                                                       
MASTER        0    0    0    0    0    0    0    0   34    0   78    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₀H₄₈O₄

Average Mass

472.7100 Da

Monoisotopic Mass

472.35526 Da

IUPAC Name

(2S,3S,4S,5S)-3-[(1S,3R,6S,8R,11S,12S,15R,16R)-6-hydroxy-7,7,12,16-tetramethylpentacyclo[9.7.0.0^{1,3}.0^{3,8}.0^{12,16}]octadecan-15-yl]-5-(2-methylprop-1-en-1-yl)oxolane-2,4-diol

Traditional Name

(2S,3S,4S,5S)-3-[(1S,3R,6S,8R,11S,12S,15R,16R)-6-hydroxy-7,7,12,16-tetramethylpentacyclo[9.7.0.0^{1,3}.0^{3,8}.0^{12,16}]octadecan-15-yl]-5-(2-methylprop-1-en-1-yl)oxolane-2,4-diol

CAS Registry Number

Not Available

SMILES

CC(C)=C[C@@H]1O[C@H](O)[C@H]([C@@H]1O)[C@H]1CC[C@@]2(C)[C@@H]3CC[C@@H]4[C@]5(C[C@@]35CC[C@]12C)CC[C@H](O)C4(C)C

InChI Identifier

InChI=1S/C30H48O4/c1-17(2)15-19-24(32)23(25(33)34-19)18-9-11-28(6)21-8-7-20-26(3,4)22(31)10-12-29(20)16-30(21,29)14-13-27(18,28)5/h15,18-25,31-33H,7-14,16H2,1-6H3/t18-,19+,20+,21+,22+,23+,24-,25+,27-,28+,29-,30+/m1/s1

InChI Key

WZYISXKEYZUNQE-LBXJHVLXSA-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 limonoids. These are highly oxygenated, modified terpenoids with a prototypical structure either containing or derived from a precursor with a 4,4,8-trimethyl-17-furanylsteroid skeleton. All naturally occurring citrus limonoids contain a furan ring attached to the D-ring, at C-17, as well as oxygen containing functional groups at C-3, C-4, C-7, C-16 and C-17.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Triterpenoids

Direct Parent

Limonoids

Alternative Parents

Substituents

Cycloartanol-skeleton
Limonoid skeleton
9b,19-cyclo-lanostane-skeleton
Cycloartane-skeleton
22-hydroxysteroid
3-hydroxysteroid
3-beta-hydroxysteroid
Hydroxysteroid
Steroid
Pentose monosaccharide
Monosaccharide
Tetrahydrofuran
Cyclic alcohol
Secondary alcohol
Hemiacetal
Organoheterocyclic compound
Oxacycle
Organooxygen compound
Hydrocarbon derivative
Alcohol
Organic oxygen compound
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic 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	4.12	ALOGPS
logP	4.83	ChemAxon
logS	-4.8	ALOGPS
pKa (Strongest Acidic)	12.06	ChemAxon
pKa (Strongest Basic)	-0.84	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	2	ChemAxon
Refractivity	133.98 m³·mol⁻¹	ChemAxon
Polarizability	56.42 Å³	ChemAxon
Number of Rings	6	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

C00050000

Chemspider ID

8918413

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10743082

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for (+)-Argenteanol C (NP0083006)

MOL for NP0083006 ((+)-Argenteanol C)

3D MOL for NP0083006 ((+)-Argenteanol C)

3D SDF for NP0083006 ((+)-Argenteanol C)

3D-SDF for NP0083006 ((+)-Argenteanol C)

PDB for NP0083006 ((+)-Argenteanol C)

3D PDB for NP0083006 ((+)-Argenteanol C)

SMILES for NP0083006 ((+)-Argenteanol C)

INCHI for NP0083006 ((+)-Argenteanol C)

Structure for NP0083006 ((+)-Argenteanol C)

3D Structure for NP0083006 ((+)-Argenteanol C)