NP-MRD: Showing NP-Card for (-)-Shinjulactone C (NP0071847)

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Record Information

Version

2.0

Created at

2022-04-28 17:13:09 UTC

Updated at

2022-04-28 17:13:09 UTC

NP-MRD ID

NP0071847

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(-)-Shinjulactone C

Description

(1S,2R,3R,7R,9R,13R,14R,15S,17S)-3,15-dihydroxy-17-(hydroxymethyl)-2,6,14-trimethyl-10-oxahexacyclo[7.7.1.0²,⁷.0³,¹⁵.0⁷,¹⁴.0¹³,¹⁷]Heptadec-5-ene-4,11,16-trione belongs to the class of organic compounds known as quassinoids. These are a group of compounds chemically degraded from triterpenes. According to their basic skeleton, quassinoids are categorized into five distinct groups, C-18, C-19, C-20, C-22 and C-25 types. The C-20 quassinoids can be further classified into two types, tetracyclic and the pentacyclic. The tetracyclic variety does not have oxygenation at C-20, while the pentacyclic quassinoids possess additional oxygenation at C-20 that allows for the formation of an additional ring. (-)-Shinjulactone C is found in Ailanthus altissima and Ailanthus altissima . Based on a literature review very few articles have been published on (1S,2R,3R,7R,9R,13R,14R,15S,17S)-3,15-dihydroxy-17-(hydroxymethyl)-2,6,14-trimethyl-10-oxahexacyclo[7.7.1.0²,⁷.0³,¹⁵.0⁷,¹⁴.0¹³,¹⁷]Heptadec-5-ene-4,11,16-trione.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652304282219132D          

 27 32  0  0  1  0            999 V2000
    3.0758    1.7457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0033    2.6198    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2141    0.7422    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.1135    0.3743    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.0055    0.3884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7675   -0.3273    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3846   -0.4623    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5462   -0.7783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8598   -0.2478    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.6041    0.3209    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.4248    1.0103    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.2910    0.9877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6643    0.2310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5491    0.3119    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1621   -0.4491    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3744    1.2974    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3970    1.1546    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5923    0.8718    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8713    1.3600    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4040    0.0303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0552   -0.5261    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9056   -1.3995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6123    0.4090    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9227    0.0065    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9673    1.9235    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9450    1.9968    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8861   -0.4417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  3  1  1  1  0  0  0
  3  4  1  0  0  0  0
  4  5  1  1  0  0  0
  5  6  1  0  0  0  0
  4  7  1  0  0  0  0
  7  8  1  0  0  0  0
  9  8  1  6  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
  4 11  1  0  0  0  0
 11 12  1  6  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
  7 15  1  6  0  0  0
 10 16  1  0  0  0  0
  1 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
 20 21  2  0  0  0  0
  9 21  1  0  0  0  0
 21 22  1  0  0  0  0
 17 23  1  0  0  0  0
  3 23  1  0  0  0  0
  9 23  1  0  0  0  0
 23 24  1  1  0  0  0
 17 25  1  1  0  0  0
 16 26  1  1  0  0  0
 10 27  1  1  0  0  0
M  END


  Mrv1652304282219132D          

 27 32  0  0  1  0            999 V2000
    3.0758    1.7457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0033    2.6198    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2141    0.7422    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.1135    0.3743    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.0055    0.3884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7675   -0.3273    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3846   -0.4623    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5462   -0.7783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8598   -0.2478    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.6041    0.3209    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.4248    1.0103    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.2910    0.9877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6643    0.2310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5491    0.3119    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1621   -0.4491    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3744    1.2974    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3970    1.1546    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5923    0.8718    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8713    1.3600    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4040    0.0303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0552   -0.5261    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9056   -1.3995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6123    0.4090    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9227    0.0065    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9673    1.9235    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9450    1.9968    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8861   -0.4417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  3  1  1  1  0  0  0
  3  4  1  0  0  0  0
  4  5  1  1  0  0  0
  5  6  1  0  0  0  0
  4  7  1  0  0  0  0
  7  8  1  0  0  0  0
  9  8  1  6  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
  4 11  1  0  0  0  0
 11 12  1  6  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
  7 15  1  6  0  0  0
 10 16  1  0  0  0  0
  1 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
 20 21  2  0  0  0  0
  9 21  1  0  0  0  0
 21 22  1  0  0  0  0
 17 23  1  0  0  0  0
  3 23  1  0  0  0  0
  9 23  1  0  0  0  0
 23 24  1  1  0  0  0
 17 25  1  1  0  0  0
 16 26  1  1  0  0  0
 10 27  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0071847

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1=CC(=O)[C@@]2(O)[C@]3(C)[C@H]4C(=O)[C@]2(O)[C@]2(C)[C@@H]5CC(=O)O[C@H](C[C@]132)[C@]45CO

> <INCHI_IDENTIFIER>
InChI=1S/C20H22O7/c1-8-4-10(22)19(25)16(3)13-14(24)20(19,26)15(2)9-5-12(23)27-11(6-18(8,15)16)17(9,13)7-21/h4,9,11,13,21,25-26H,5-7H2,1-3H3/t9-,11+,13+,15+,16+,17+,18+,19+,20-/m0/s1

> <INCHI_KEY>
QUDGSOQXSJGXMH-HHIPSTAOSA-N

> <FORMULA>
C20H22O7

> <MOLECULAR_WEIGHT>
374.389

> <EXACT_MASS>
374.136553048

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
49

> <JCHEM_AVERAGE_POLARIZABILITY>
37.763013324774775

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,2R,3R,7R,9R,13R,14R,15S,17S)-3,15-dihydroxy-17-(hydroxymethyl)-2,6,14-trimethyl-10-oxahexacyclo[7.7.1.0^{2,7}.0^{3,15}.0^{7,14}.0^{13,17}]heptadec-5-ene-4,11,16-trione

> <ALOGPS_LOGP>
0.32

> <JCHEM_LOGP>
-0.9463190383333331

> <ALOGPS_LOGS>
-1.54

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.316391173216864

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.613934129978665

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8016288694418057

> <JCHEM_POLAR_SURFACE_AREA>
121.13

> <JCHEM_REFRACTIVITY>
89.9786

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.09e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2R,3R,7R,9R,13R,14R,15S,17S)-3,15-dihydroxy-17-(hydroxymethyl)-2,6,14-trimethyl-10-oxahexacyclo[7.7.1.0^{2,7}.0^{3,15}.0^{7,14}.0^{13,17}]heptadec-5-ene-4,11,16-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       5.742   3.259   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       5.606   4.890   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       6.000   1.385   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.679   0.699   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       9.344   0.725   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      10.766  -0.611   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       8.185  -0.863   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.620  -1.453   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.338  -0.463   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.728   0.599   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.260   1.886   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       9.877   1.844   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      10.573   0.431   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      12.225   0.582   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0       9.636  -0.838   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       6.299   2.422   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.474   2.155   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.972   1.627   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       1.626   2.539   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       2.621   0.057   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       3.836  -0.982   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       3.557  -2.612   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       4.876   0.763   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       3.589   0.012   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       3.672   3.590   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0       7.364   3.727   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       7.254  -0.824   0.000  0.00  0.00           C+0
CONECT    1    2    3   16                                                  
CONECT    2    1                                                            
CONECT    3    1    4   23                                                  
CONECT    4    3    5    7   11                                             
CONECT    5    4    6                                                       
CONECT    6    5                                                            
CONECT    7    4    8   15                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   21   23                                             
CONECT   10    9   11   16   27                                             
CONECT   11   10    4   12                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13    7                                                       
CONECT   16   10    1   17   26                                             
CONECT   17   16   18   23   25                                             
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21                                                       
CONECT   21   20    9   22                                                  
CONECT   22   21                                                            
CONECT   23   17    3    9   24                                             
CONECT   24   23                                                            
CONECT   25   17                                                            
CONECT   26   16                                                            
CONECT   27   10                                                            
MASTER        0    0    0    0    0    0    0    0   27    0   64    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₀H₂₂O₇

Average Mass

374.3890 Da

Monoisotopic Mass

374.13655 Da

IUPAC Name

(1S,2R,3R,7R,9R,13R,14R,15S,17S)-3,15-dihydroxy-17-(hydroxymethyl)-2,6,14-trimethyl-10-oxahexacyclo[7.7.1.0^{2,7}.0^{3,15}.0^{7,14}.0^{13,17}]heptadec-5-ene-4,11,16-trione

Traditional Name

(1S,2R,3R,7R,9R,13R,14R,15S,17S)-3,15-dihydroxy-17-(hydroxymethyl)-2,6,14-trimethyl-10-oxahexacyclo[7.7.1.0^{2,7}.0^{3,15}.0^{7,14}.0^{13,17}]heptadec-5-ene-4,11,16-trione

CAS Registry Number

Not Available

SMILES

CC1=CC(=O)[C@@]2(O)[C@]3(C)[C@H]4C(=O)[C@]2(O)[C@]2(C)[C@@H]5CC(=O)O[C@H](C[C@]132)[C@]45CO

InChI Identifier

InChI=1S/C20H22O7/c1-8-4-10(22)19(25)16(3)13-14(24)20(19,26)15(2)9-5-12(23)27-11(6-18(8,15)16)17(9,13)7-21/h4,9,11,13,21,25-26H,5-7H2,1-3H3/t9-,11+,13+,15+,16+,17+,18+,19+,20-/m0/s1

InChI Key

QUDGSOQXSJGXMH-HHIPSTAOSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Ailanthus altissima	LOTUS Database	35616633
Ailanthus altissimus	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as quassinoids. These are a group of compounds chemically degraded from triterpenes. According to their basic skeleton, quassinoids are categorized into five distinct groups, C-18, C-19, C-20, C-22 and C-25 types. The C-20 quassinoids can be further classified into two types, tetracyclic and the pentacyclic. The tetracyclic variety does not have oxygenation at C-20, while the pentacyclic quassinoids possess additional oxygenation at C-20 that allows for the formation of an additional ring.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Quassinoids

Alternative Parents

Substituents

Polycyclic triterpenoid
Triterpenoid
C-20 quassinoid skeleton
Quassinoid
Naphthopyran
Naphthalene
Cyclohexenone
Delta_valerolactone
Delta valerolactone
Pyran
Oxane
Tertiary alcohol
Cyclic alcohol
Lactone
Ketone
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Carboxylic acid derivative
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	0.32	ALOGPS
logP	-0.95	ChemAxon
logS	-1.5	ALOGPS
pKa (Strongest Acidic)	10.61	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	121.13 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	89.98 m³·mol⁻¹	ChemAxon
Polarizability	37.76 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

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

162977650

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for (-)-Shinjulactone C (NP0071847)

MOL for NP0071847 ((-)-Shinjulactone C)

3D MOL for NP0071847 ((-)-Shinjulactone C)

3D SDF for NP0071847 ((-)-Shinjulactone C)

3D-SDF for NP0071847 ((-)-Shinjulactone C)

PDB for NP0071847 ((-)-Shinjulactone C)

3D PDB for NP0071847 ((-)-Shinjulactone C)

SMILES for NP0071847 ((-)-Shinjulactone C)

INCHI for NP0071847 ((-)-Shinjulactone C)

Structure for NP0071847 ((-)-Shinjulactone C)

3D Structure for NP0071847 ((-)-Shinjulactone C)