NP-MRD: Showing NP-Card for (+)-Saponaceolide B (NP0073169)

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Record Information

Version

2.0

Created at

2022-04-28 18:25:55 UTC

Updated at

2022-04-28 18:25:55 UTC

NP-MRD ID

NP0073169

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(+)-Saponaceolide B

Description

Saponaceolide B belongs to the class of organic compounds known as ketals. These are acetals derived from ketones by replacement of the oxo group by two hydrocarbyloxy groups R2C(OR)2 ( R not Hydrogen ). This term, once abandoned, has been reinstated as a subclass of acetals. (+)-Saponaceolide B is found in Tricholoma saponaceum , Tricholoma scalpturatum and Tricholoma terreum. (+)-Saponaceolide B was first documented in 2014 (PMID: 24753190). Based on a literature review very few articles have been published on Saponaceolide B.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282220252D          

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M  END

     RDKit          3D

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M  END


  Mrv1652304282220252D          

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   10.0594    1.9573    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4902    1.8333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1881    2.1694    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3964    1.7764    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  3  2  1  6  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  1  0  0  0  0
  6  8  1  0  0  0  0
  4  9  1  6  0  0  0
  4 10  1  0  0  0  0
 10 11  1  0  0  0  0
  1 11  1  0  0  0  0
  3 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  1  0  0  0  0
  3 16  1  0  0  0  0
 14 17  1  6  0  0  0
 17 18  1  0  0  0  0
 19 18  1  1  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  2  0  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
 19 25  1  0  0  0  0
 21 26  1  1  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 28 32  1  0  0  0  0
 32 33  2  0  0  0  0
 20 34  1  0  0  0  0
 20 35  1  0  0  0  0
  1 36  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0073169

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1(C)O[C@@]2(C)CC[C@]1(O)O[C@@]21CC[C@H](CC[C@@H]2CCC(=C)[C@H](C\C=C3/CCOC3=O)C2(C)C)CO1

> <INCHI_IDENTIFIER>
InChI=1S/C30H46O6/c1-20-7-10-23(26(2,3)24(20)12-9-22-14-18-33-25(22)31)11-8-21-13-15-30(34-19-21)28(6)16-17-29(32,36-30)27(4,5)35-28/h9,21,23-24,32H,1,7-8,10-19H2,2-6H3/b22-9+/t21-,23-,24-,28-,29-,30-/m0/s1

> <INCHI_KEY>
SCWVCRCOVNDPJB-RQKPTXGCSA-N

> <FORMULA>
C30H46O6

> <MOLECULAR_WEIGHT>
502.692

> <EXACT_MASS>
502.329439201

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
82

> <JCHEM_AVERAGE_POLARIZABILITY>
57.77755618693692

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(3E)-3-{2-[(1S,3R)-3-{2-[(1S,2S,4S,5'S)-4-hydroxy-1,5,5-trimethyl-3,6-dioxaspiro[bicyclo[2.2.2]octane-2,2'-oxane]-5'-yl]ethyl}-2,2-dimethyl-6-methylidenecyclohexyl]ethylidene}oxolan-2-one

> <ALOGPS_LOGP>
4.94

> <JCHEM_LOGP>
6.107266964666667

> <ALOGPS_LOGS>
-6.03

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.93171241686637

> <JCHEM_PKA_STRONGEST_BASIC>
-3.9118002794539293

> <JCHEM_POLAR_SURFACE_AREA>
74.22

> <JCHEM_REFRACTIVITY>
139.0611

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.69e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3E)-3-{2-[(1S,3R)-3-{2-[(1S,2S,4S,5'S)-4-hydroxy-1,5,5-trimethyl-3,6-dioxaspiro[bicyclo[2.2.2]octane-2,2'-oxane]-5'-yl]ethyl}-2,2-dimethyl-6-methylidenecyclohexyl]ethylidene}oxolan-2-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       1.408   1.928   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       2.944   1.813   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       3.612   0.426   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.745  -0.847   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       1.209  -0.732   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       0.541   0.656   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.869   0.037   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.761   1.478   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.413  -2.234   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.068  -0.033   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.622   0.892   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.479   1.698   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.015   1.583   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.683   0.196   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.816  -1.077   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       4.280  -0.962   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       8.219   0.081   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       9.087   1.353   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      10.622   1.238   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      11.490   2.511   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      13.025   2.396   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      13.694   1.008   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      15.229   0.893   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      12.826  -0.264   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      11.291  -0.149   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      13.893   3.668   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      15.429   3.553   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      16.296   4.826   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      15.777   6.275   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      16.995   7.217   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      18.267   6.350   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      17.835   4.872   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      18.777   3.654   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0      10.248   3.422   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      11.551   4.050   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0       0.740   3.316   0.000  0.00  0.00           O+0
CONECT    1    2    6   11   36                                             
CONECT    2    1    3                                                       
CONECT    3    2    4   12   16                                             
CONECT    4    3    5    9   10                                             
CONECT    5    4    6                                                       
CONECT    6    5    1    7    8                                             
CONECT    7    6                                                            
CONECT    8    6                                                            
CONECT    9    4                                                            
CONECT   10    4   11                                                       
CONECT   11   10    1                                                       
CONECT   12    3   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   17                                                  
CONECT   15   14   16                                                       
CONECT   16   15    3                                                       
CONECT   17   14   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   25                                                  
CONECT   20   19   21   34   35                                             
CONECT   21   20   22   26                                                  
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25                                                       
CONECT   25   24   19                                                       
CONECT   26   21   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29   32                                                  
CONECT   29   28   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   28   33                                                  
CONECT   33   32                                                            
CONECT   34   20                                                            
CONECT   35   20                                                            
CONECT   36    1                                                            
MASTER        0    0    0    0    0    0    0    0   36    0   80    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₀H₄₆O₆

Average Mass

502.6920 Da

Monoisotopic Mass

502.32944 Da

IUPAC Name

(3E)-3-{2-[(1S,3R)-3-{2-[(1S,2S,4S,5'S)-4-hydroxy-1,5,5-trimethyl-3,6-dioxaspiro[bicyclo[2.2.2]octane-2,2'-oxane]-5'-yl]ethyl}-2,2-dimethyl-6-methylidenecyclohexyl]ethylidene}oxolan-2-one

Traditional Name

(3E)-3-{2-[(1S,3R)-3-{2-[(1S,2S,4S,5'S)-4-hydroxy-1,5,5-trimethyl-3,6-dioxaspiro[bicyclo[2.2.2]octane-2,2'-oxane]-5'-yl]ethyl}-2,2-dimethyl-6-methylidenecyclohexyl]ethylidene}oxolan-2-one

CAS Registry Number

Not Available

SMILES

CC1(C)O[C@@]2(C)CC[C@]1(O)O[C@@]21CC[C@H](CC[C@@H]2CCC(=C)[C@H](C\C=C3/CCOC3=O)C2(C)C)CO1

InChI Identifier

InChI=1S/C30H46O6/c1-20-7-10-23(26(2,3)24(20)12-9-22-14-18-33-25(22)31)11-8-21-13-15-30(34-19-21)28(6)16-17-29(32,36-30)27(4,5)35-28/h9,21,23-24,32H,1,7-8,10-19H2,2-6H3/b22-9+/t21-,23-,24-,28-,29-,30-/m0/s1

InChI Key

SCWVCRCOVNDPJB-RQKPTXGCSA-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
Tricholoma saponaceum	Fungi	KNApSAcK
Tricholoma scalpturatum	LOTUS Database	35616633
Tricholoma terreum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as ketals. These are acetals derived from ketones by replacement of the oxo group by two hydrocarbyloxy groups R2C(OR)2 ( R not Hydrogen ). This term, once abandoned, has been reinstated as a subclass of acetals.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Ethers

Direct Parent

Ketals

Alternative Parents

Substituents

Ketal
Para-dioxane
Gamma butyrolactone
Oxane
Oxolane
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Carboxylic acid ester
Hemiacetal
Lactone
Dialkyl ether
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Oxacycle
Organoheterocyclic compound
Carbonyl group
Hydrocarbon derivative
Organic oxide
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	4.94	ALOGPS
logP	6.11	ChemAxon
logS	-6	ALOGPS
pKa (Strongest Acidic)	10.93	ChemAxon
pKa (Strongest Basic)	-3.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	74.22 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	139.06 m³·mol⁻¹	ChemAxon
Polarizability	57.78 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	No	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

C00033355

Chemspider ID

9213608

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11038434

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Yin X, Feng T, Shang JH, Zhao YL, Wang F, Li ZH, Dong ZJ, Luo XD, Liu JK: Chemical and toxicological investigations of a previously unknown poisonous European mushroom Tricholoma terreum. Chemistry. 2014 Jun 2;20(23):7001-9. doi: 10.1002/chem.201400226. Epub 2014 Apr 17. [PubMed:24753190 ]

Showing NP-Card for (+)-Saponaceolide B (NP0073169)

MOL for NP0073169 ((+)-Saponaceolide B)

3D MOL for NP0073169 ((+)-Saponaceolide B)

3D SDF for NP0073169 ((+)-Saponaceolide B)

3D-SDF for NP0073169 ((+)-Saponaceolide B)

PDB for NP0073169 ((+)-Saponaceolide B)

3D PDB for NP0073169 ((+)-Saponaceolide B)

SMILES for NP0073169 ((+)-Saponaceolide B)

INCHI for NP0073169 ((+)-Saponaceolide B)

Structure for NP0073169 ((+)-Saponaceolide B)

3D Structure for NP0073169 ((+)-Saponaceolide B)