NP-MRD: Showing NP-Card for Holstinone C (NP0076653)

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Record Information

Version

2.0

Created at

2022-04-28 21:50:37 UTC

Updated at

2022-04-28 21:50:38 UTC

NP-MRD ID

NP0076653

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Holstinone C

Description

(1R,2R,7R,9R,10R,14S,15S)-14-[(2R,3S,5R)-5-[(1R)-1,2-dihydroxy-2-methylpropyl]-2-methoxyoxolan-3-yl]-9-hydroxy-2,6,6,10,15-pentamethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadeca-3,11-dien-5-one 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. Holstinone C is found in Turraea holstii . Based on a literature review very few articles have been published on (1R,2R,7R,9R,10R,14S,15S)-14-[(2R,3S,5R)-5-[(1R)-1,2-dihydroxy-2-methylpropyl]-2-methoxyoxolan-3-yl]-9-hydroxy-2,6,6,10,15-pentamethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadeca-3,11-dien-5-one.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282223502D          

 37 41  0  0  1  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652304282223502D          

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    1.2889   -1.5854    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6061   -2.0484    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0452   -1.5420    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2351   -0.7661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8377   -1.7713    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4326   -1.1996    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0354   -2.5723    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2331   -3.3733    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8364   -2.3746    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2344   -2.7699    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0648   -1.8657    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2101   -2.6778    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0307   -0.9107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9511    1.3835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2314    2.1594    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5466   -0.5086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  1  6  1  0  0  0  0
  6  7  2  0  0  0  0
  5  8  1  0  0  0  0
  5  9  1  0  0  0  0
  4 10  1  1  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
  3 13  1  0  0  0  0
 13 14  1  1  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 12 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 16 20  1  0  0  0  0
 20 21  1  6  0  0  0
 21 22  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
 21 25  1  1  0  0  0
 24 26  1  1  0  0  0
 26 27  1  6  0  0  0
 26 28  1  0  0  0  0
 28 29  1  0  0  0  0
 28 30  1  0  0  0  0
 28 31  1  0  0  0  0
 22 32  1  6  0  0  0
 32 33  1  0  0  0  0
 16 34  1  6  0  0  0
 12 35  1  1  0  0  0
 11 36  1  6  0  0  0
  3 37  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0076653

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CO[C@@H]1O[C@H](C[C@H]1[C@@H]1CC=C2[C@@]1(C)CC[C@@H]1[C@@]3(C)C=CC(=O)C(C)(C)[C@@H]3C[C@@H](O)[C@@]21C)[C@@H](O)C(C)(C)O

> <INCHI_IDENTIFIER>
InChI=1S/C31H48O6/c1-27(2)22-16-24(33)31(7)20-10-9-18(17-15-19(37-26(17)36-8)25(34)28(3,4)35)29(20,5)13-11-21(31)30(22,6)14-12-23(27)32/h10,12,14,17-19,21-22,24-26,33-35H,9,11,13,15-16H2,1-8H3/t17-,18-,19+,21+,22-,24+,25+,26+,29-,30+,31-/m0/s1

> <INCHI_KEY>
XCCPYESNSWQOFT-NFEZNXCZSA-N

> <FORMULA>
C31H48O6

> <MOLECULAR_WEIGHT>
516.719

> <EXACT_MASS>
516.345089266

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
85

> <JCHEM_AVERAGE_POLARIZABILITY>
59.05313577592785

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,2R,7R,9R,10R,14S,15S)-14-[(2R,3S,5R)-5-[(1R)-1,2-dihydroxy-2-methylpropyl]-2-methoxyoxolan-3-yl]-9-hydroxy-2,6,6,10,15-pentamethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-3,11-dien-5-one

> <ALOGPS_LOGP>
3.88

> <JCHEM_LOGP>
3.8330585710000005

> <ALOGPS_LOGS>
-4.95

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.09942127729288

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.050987502857872

> <JCHEM_PKA_STRONGEST_BASIC>
-0.30369756429642336

> <JCHEM_POLAR_SURFACE_AREA>
96.22000000000001

> <JCHEM_REFRACTIVITY>
144.48480000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
5.76e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2R,7R,9R,10R,14S,15S)-14-[(2R,3S,5R)-5-[(1R)-1,2-dihydroxy-2-methylpropyl]-2-methoxyoxolan-3-yl]-9-hydroxy-2,6,6,10,15-pentamethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-3,11-dien-5-one

> <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      10.003  -0.678   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       9.010   0.499   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      11.049   2.218   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      12.042   1.041   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      13.558   1.312   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      10.831   3.743   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      12.191   3.252   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.541   3.125   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.025   2.854   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.502   1.405   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.494   0.228   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.971  -1.221   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.455  -1.492   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.462  -0.314   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.986   1.134   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.770   2.079   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.495   1.215   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.923  -0.264   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       1.978  -1.480   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       2.406  -2.959   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       1.131  -3.824   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      -0.084  -2.878   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       0.439  -1.430   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -1.564  -3.306   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      -2.674  -2.239   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      -1.933  -4.802   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      -2.302  -6.297   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      -3.428  -4.433   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -0.438  -5.171   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       3.854  -3.483   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       4.125  -4.999   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       3.791  -1.700   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       5.509   2.583   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0       6.032   4.031   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0       8.487  -0.949   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4   13   37                                             
CONECT    4    3    5   10                                                  
CONECT    5    4    6    8    9                                             
CONECT    6    5    1    7                                                  
CONECT    7    6                                                            
CONECT    8    5                                                            
CONECT    9    5                                                            
CONECT   10    4   11                                                       
CONECT   11   10   12   36                                                  
CONECT   12   11   13   17   35                                             
CONECT   13   12    3   14                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   20   34                                             
CONECT   17   16   12   18                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   16   21                                                  
CONECT   21   20   22   25                                                  
CONECT   22   21   23   32                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25   26                                                  
CONECT   25   24   21                                                       
CONECT   26   24   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   29   30   31                                             
CONECT   29   28                                                            
CONECT   30   28                                                            
CONECT   31   28                                                            
CONECT   32   22   33                                                       
CONECT   33   32                                                            
CONECT   34   16                                                            
CONECT   35   12                                                            
CONECT   36   11                                                            
CONECT   37    3                                                            
MASTER        0    0    0    0    0    0    0    0   37    0   82    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₁H₄₈O₆

Average Mass

516.7190 Da

Monoisotopic Mass

516.34509 Da

IUPAC Name

(1R,2R,7R,9R,10R,14S,15S)-14-[(2R,3S,5R)-5-[(1R)-1,2-dihydroxy-2-methylpropyl]-2-methoxyoxolan-3-yl]-9-hydroxy-2,6,6,10,15-pentamethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-3,11-dien-5-one

Traditional Name

(1R,2R,7R,9R,10R,14S,15S)-14-[(2R,3S,5R)-5-[(1R)-1,2-dihydroxy-2-methylpropyl]-2-methoxyoxolan-3-yl]-9-hydroxy-2,6,6,10,15-pentamethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-3,11-dien-5-one

CAS Registry Number

Not Available

SMILES

CO[C@@H]1O[C@H](C[C@H]1[C@@H]1CC=C2[C@@]1(C)CC[C@@H]1[C@@]3(C)C=CC(=O)C(C)(C)[C@@H]3C[C@@H](O)[C@@]21C)[C@@H](O)C(C)(C)O

InChI Identifier

InChI=1S/C31H48O6/c1-27(2)22-16-24(33)31(7)20-10-9-18(17-15-19(37-26(17)36-8)25(34)28(3,4)35)29(20,5)13-11-21(31)30(22,6)14-12-23(27)32/h10,12,14,17-19,21-22,24-26,33-35H,9,11,13,15-16H2,1-8H3/t17-,18-,19+,21+,22-,24+,25+,26+,29-,30+,31-/m0/s1

InChI Key

XCCPYESNSWQOFT-NFEZNXCZSA-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
Turraea holstii	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

Limonoid skeleton
24-hydroxysteroid
Dihydroxy bile acid, alcohol, or derivatives
Hydroxy bile acid, alcohol, or derivatives
Bile acid, alcohol, or derivatives
3-oxo-5-alpha-steroid
7-hydroxysteroid
Oxosteroid
Hydroxysteroid
3-oxosteroid
3-oxo-delta-1-steroid
Steroid
Delta-1-steroid
Cyclohexenone
Tetrahydrofuran
Tertiary alcohol
Cyclic alcohol
Cyclic ketone
Secondary alcohol
Ketone
Oxacycle
Organoheterocyclic compound
Acetal
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
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	3.88	ALOGPS
logP	3.83	ChemAxon
logS	-5	ALOGPS
pKa (Strongest Acidic)	13.05	ChemAxon
pKa (Strongest Basic)	-0.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	96.22 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	144.48 m³·mol⁻¹	ChemAxon
Polarizability	59.05 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	No	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

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

162884473

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for Holstinone C (NP0076653)

MOL for NP0076653 (Holstinone C)

3D MOL for NP0076653 (Holstinone C)

3D SDF for NP0076653 (Holstinone C)

3D-SDF for NP0076653 (Holstinone C)

PDB for NP0076653 (Holstinone C)

3D PDB for NP0076653 (Holstinone C)

SMILES for NP0076653 (Holstinone C)

INCHI for NP0076653 (Holstinone C)

Structure for NP0076653 (Holstinone C)

3D Structure for NP0076653 (Holstinone C)