NP-MRD: Showing NP-Card for (+)-Sphenadilactone A (NP0073744)

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Record Information

Version

2.0

Created at

2022-04-28 18:58:09 UTC

Updated at

2022-04-28 18:58:09 UTC

NP-MRD ID

NP0073744

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(+)-Sphenadilactone A

Description

(1S,3R,7R,9R,10S,13S,14S,16R,17R,19R,20S,21R,24S,25R,27S,30S)-14,19-dihydroxy-9-(hydroxymethyl)-9,17,19,24-tetramethyl-4,8,15,22,26,28-hexaoxanonacyclo[14.12.1.1¹⁷,²⁰.0¹,¹³.0³,⁷.0³,¹⁰.0¹⁴,²⁷.0²¹,²⁵.0²⁷,³⁰]Triacontane-5,18,23-trione belongs to the class of organic compounds known as furopyrans. These are organic polycyclic compounds containing a furan ring fused to a pyran ring. Furan is a five-membered aromatic ring with four carbon atoms and one oxygen atom. Pyran a six-membered heterocyclic, non-aromatic ring, made up of five carbon atoms and one oxygen atom and containing two double bonds. (+)-Sphenadilactone A is found in Schisandra sphenanthera . Based on a literature review very few articles have been published on (1S,3R,7R,9R,10S,13S,14S,16R,17R,19R,20S,21R,24S,25R,27S,30S)-14,19-dihydroxy-9-(hydroxymethyl)-9,17,19,24-tetramethyl-4,8,15,22,26,28-hexaoxanonacyclo[14.12.1.1¹⁷,²⁰.0¹,¹³.0³,⁷.0³,¹⁰.0¹⁴,²⁷.0²¹,²⁵.0²⁷,³⁰]Triacontane-5,18,23-trione.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282220582D          

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M  END

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M  END


  Mrv1652304282220582D          

 41 49  0  0  1  0            999 V2000
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    2.9372   -1.6714    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.7730   -1.6239    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3500   -1.0920    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6174   -1.4714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8798   -1.1019    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7520   -2.2854    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4735   -0.2763    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5204   -4.6944    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0578   -3.3420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6816   -2.9304    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1011   -1.1063    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.6260   -1.7428    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1830   -2.4387    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.2336   -3.2621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4661   -3.5647    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2598   -4.3635    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9411   -2.9283    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8887   -0.3091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6730   -0.5117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4739   -0.7097    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  1  0  0  0
  3  4  1  0  0  0  0
  5  4  1  1  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  1  7  1  0  0  0  0
  6  8  1  0  0  0  0
  9  8  1  6  0  0  0
  9 10  1  0  0  0  0
  5 10  1  0  0  0  0
 10 11  1  0  0  0  0
 12 11  1  1  0  0  0
 12 13  1  0  0  0  0
 14 13  1  6  0  0  0
  9 14  1  0  0  0  0
 15 14  1  6  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 13 17  1  0  0  0  0
 17 18  2  0  0  0  0
 16 19  1  6  0  0  0
 16 20  1  1  0  0  0
 15 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  1  0  0  0
  9 23  1  0  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 25 27  1  0  0  0  0
 21 27  1  1  0  0  0
 24 28  1  1  0  0  0
 13 29  1  1  0  0  0
 12 30  1  0  0  0  0
  6 30  1  1  0  0  0
 10 31  1  1  0  0  0
  2 32  1  0  0  0  0
 32 33  1  0  0  0  0
 34 33  1  6  0  0  0
  1 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 36 37  2  0  0  0  0
 36 38  1  0  0  0  0
  1 38  1  6  0  0  0
 32 39  1  1  0  0  0
 32 40  1  6  0  0  0
 40 41  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0073744

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@H]1[C@H]2O[C@@]34O[C@]56C[C@@H](O[C@@]3(O)[C@H]5CC[C@H]3[C@](C)(CO)O[C@@H]5CC(=O)O[C@]35C6)[C@@]3(C)[C@@H]4[C@@H]([C@H]2OC1=O)[C@@](C)(O)C3=O

> <INCHI_IDENTIFIER>
InChI=1S/C29H36O12/c1-11-18-19(36-21(11)32)17-20-24(3,22(33)25(17,4)34)15-8-26-9-27-12(23(2,10-30)37-14(27)7-16(31)39-27)5-6-13(26)28(35,38-15)29(20,40-18)41-26/h11-15,17-20,30,34-35H,5-10H2,1-4H3/t11-,12-,13-,14+,15+,17+,18+,19+,20-,23-,24-,25+,26-,27+,28-,29-/m0/s1

> <INCHI_KEY>
NJTZWXJTMLGIFW-QISOINHRSA-N

> <FORMULA>
C29H36O12

> <MOLECULAR_WEIGHT>
576.595

> <EXACT_MASS>
576.220676599

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
77

> <JCHEM_AVERAGE_POLARIZABILITY>
57.02548131403305

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,3R,7R,9R,10S,13S,14S,16R,17R,19R,20S,21R,24S,25R,27S,30S)-14,19-dihydroxy-9-(hydroxymethyl)-9,17,19,24-tetramethyl-4,8,15,22,26,28-hexaoxanonacyclo[14.12.1.1^{17,20}.0^{1,13}.0^{3,7}.0^{3,10}.0^{14,27}.0^{21,25}.0^{27,30}]triacontane-5,18,23-trione

> <ALOGPS_LOGP>
0.46

> <JCHEM_LOGP>
0.28042678633333207

> <ALOGPS_LOGS>
-2.32

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
9

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.910161971090975

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.985966024249679

> <JCHEM_PKA_STRONGEST_BASIC>
-3.078302531802243

> <JCHEM_POLAR_SURFACE_AREA>
167.28

> <JCHEM_REFRACTIVITY>
131.32309999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.77e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,3R,7R,9R,10S,13S,14S,16R,17R,19R,20S,21R,24S,25R,27S,30S)-14,19-dihydroxy-9-(hydroxymethyl)-9,17,19,24-tetramethyl-4,8,15,22,26,28-hexaoxanonacyclo[14.12.1.1^{17,20}.0^{1,13}.0^{3,7}.0^{3,10}.0^{14,27}.0^{21,25}.0^{27,30}]triacontane-5,18,23-trione

> <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      13.784  -4.167   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      13.689  -2.630   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      12.429  -1.746   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      10.951  -2.180   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      10.369  -3.606   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      11.121  -4.949   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      12.448  -5.099   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       9.349  -3.222   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       8.007  -4.321   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.169  -4.916   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       9.179  -6.597   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       9.913  -7.230   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.968  -7.296   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.164  -5.771   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.632  -5.843   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.286  -7.380   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.616  -8.195   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       6.644  -9.735   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       4.342  -8.597   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       3.755  -7.209   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.793  -4.497   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       5.483  -3.120   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       7.043  -3.031   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       4.387  -2.038   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       3.019  -2.747   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       1.642  -2.057   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0       3.270  -4.266   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       4.617  -0.516   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       8.438  -8.763   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      11.308  -6.238   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      10.606  -5.470   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      15.122  -2.065   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      16.102  -3.253   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0      15.275  -4.552   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      15.369  -6.089   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      13.937  -6.654   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0      13.552  -8.145   0.000  0.00  0.00           O+0
HETATM   38  O   UNK     0      12.957  -5.466   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0      14.726  -0.577   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      16.190  -0.955   0.000  0.00  0.00           C+0
HETATM   41  O   UNK     0      17.685  -1.325   0.000  0.00  0.00           O+0
CONECT    1    2    7   34   38                                             
CONECT    2    1    3   32                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   10                                                  
CONECT    6    5    7    8   30                                             
CONECT    7    6    1                                                       
CONECT    8    6    9                                                       
CONECT    9    8   10   14   23                                             
CONECT   10    9    5   11   31                                             
CONECT   11   10   12                                                       
CONECT   12   11   13   30                                                  
CONECT   13   12   14   17   29                                             
CONECT   14   13    9   15                                                  
CONECT   15   14   16   21                                                  
CONECT   16   15   17   19   20                                             
CONECT   17   16   13   18                                                  
CONECT   18   17                                                            
CONECT   19   16                                                            
CONECT   20   16                                                            
CONECT   21   15   22   27                                                  
CONECT   22   21   23   24                                                  
CONECT   23   22    9                                                       
CONECT   24   22   25   28                                                  
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   21                                                       
CONECT   28   24                                                            
CONECT   29   13                                                            
CONECT   30   12    6                                                       
CONECT   31   10                                                            
CONECT   32    2   33   39   40                                             
CONECT   33   32   34                                                       
CONECT   34   33    1   35                                                  
CONECT   35   34   36                                                       
CONECT   36   35   37   38                                                  
CONECT   37   36                                                            
CONECT   38   36    1                                                       
CONECT   39   32                                                            
CONECT   40   32   41                                                       
CONECT   41   40                                                            
MASTER        0    0    0    0    0    0    0    0   41    0   98    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₉H₃₆O₁₂

Average Mass

576.5950 Da

Monoisotopic Mass

576.22068 Da

IUPAC Name

Traditional Name

CAS Registry Number

Not Available

SMILES

C[C@H]1[C@H]2O[C@@]34O[C@]56C[C@@H](O[C@@]3(O)[C@H]5CC[C@H]3[C@](C)(CO)O[C@@H]5CC(=O)O[C@]35C6)[C@@]3(C)[C@@H]4[C@@H]([C@H]2OC1=O)[C@@](C)(O)C3=O

InChI Identifier

InChI=1S/C29H36O12/c1-11-18-19(36-21(11)32)17-20-24(3,22(33)25(17,4)34)15-8-26-9-27-12(23(2,10-30)37-14(27)7-16(31)39-27)5-6-13(26)28(35,38-15)29(20,40-18)41-26/h11-15,17-20,30,34-35H,5-10H2,1-4H3/t11-,12-,13-,14+,15+,17+,18+,19+,20-,23-,24-,25+,26-,27+,28-,29-/m0/s1

InChI Key

NJTZWXJTMLGIFW-QISOINHRSA-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
Schisandra sphenanthera	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as furopyrans. These are organic polycyclic compounds containing a furan ring fused to a pyran ring. Furan is a five-membered aromatic ring with four carbon atoms and one oxygen atom. Pyran a six-membered heterocyclic, non-aromatic ring, made up of five carbon atoms and one oxygen atom and containing two double bonds.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Furopyrans

Sub Class

Not Available

Direct Parent

Furopyrans

Alternative Parents

Substituents

Furopyran
Furofuran
Ketal
Oxepane
Dioxepane
1,4-dioxepane
Pyran
Oxane
Monosaccharide
Gamma butyrolactone
Dicarboxylic acid or derivatives
Acyloin
Tetrahydrofuran
Tertiary alcohol
Furan
Cyclic alcohol
Lactone
Ketone
Hemiacetal
Carboxylic acid ester
Oxacycle
Ether
Dialkyl ether
Carboxylic acid derivative
Acetal
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Primary alcohol
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	0.46	ALOGPS
logP	0.28	ChemAxon
logS	-2.3	ALOGPS
pKa (Strongest Acidic)	9.99	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	167.28 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	131.32 m³·mol⁻¹	ChemAxon
Polarizability	57.03 Å³	ChemAxon
Number of Rings	9	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

162928862

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for (+)-Sphenadilactone A (NP0073744)

MOL for NP0073744 ((+)-Sphenadilactone A)

3D MOL for NP0073744 ((+)-Sphenadilactone A)

3D SDF for NP0073744 ((+)-Sphenadilactone A)

3D-SDF for NP0073744 ((+)-Sphenadilactone A)

PDB for NP0073744 ((+)-Sphenadilactone A)

3D PDB for NP0073744 ((+)-Sphenadilactone A)

SMILES for NP0073744 ((+)-Sphenadilactone A)

INCHI for NP0073744 ((+)-Sphenadilactone A)

Structure for NP0073744 ((+)-Sphenadilactone A)

3D Structure for NP0073744 ((+)-Sphenadilactone A)