NP-MRD: Showing NP-Card for (+)-Ailantinol G (NP0071953)

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Record Information

Version

2.0

Created at

2022-04-28 17:20:44 UTC

Updated at

2022-04-28 17:20:44 UTC

NP-MRD ID

NP0071953

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(+)-Ailantinol G

Description

Ailantinol G 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. (+)-Ailantinol G is found in Ailanthus altissima, Ailanthus altissima and Ailanthus excelsa. (+)-Ailantinol G was first documented in 2003 (PMID: 12672989). Based on a literature review very few articles have been published on Ailantinol G.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282219202D          

 34 38  0  0  1  0            999 V2000
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    1.0397   -1.1761    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
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M  END

     RDKit          3D

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M  END


  Mrv1652304282219202D          

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M  END
> <DATABASE_ID>
NP0071953

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC[C@](C)(O)C(=O)O[C@@H]1[C@H]2[C@@H](C)[C@@H](O)[C@]3(O)OC[C@]22[C@@H](C[C@](C)([C@H]4OC(=O)C=C4C)[C@@H]32)OC1=O

> <INCHI_IDENTIFIER>
InChI=1S/C24H32O10/c1-6-22(5,29)20(28)34-15-14-11(3)16(26)24(30)19-21(4,17-10(2)7-13(25)33-17)8-12(32-18(15)27)23(14,19)9-31-24/h7,11-12,14-17,19,26,29-30H,6,8-9H2,1-5H3/t11-,12-,14-,15-,16-,17+,19-,21-,22+,23+,24+/m1/s1

> <INCHI_KEY>
OTNSHYRETRNONW-KIBZZZOKSA-N

> <FORMULA>
C24H32O10

> <MOLECULAR_WEIGHT>
480.51

> <EXACT_MASS>
480.19954723

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
66

> <JCHEM_AVERAGE_POLARIZABILITY>
47.06627271682643

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,2R,3S,5R,8R,9S,10R,11R,12R)-11,12-dihydroxy-3,10-dimethyl-3-[(2S)-3-methyl-5-oxo-2,5-dihydrofuran-2-yl]-7-oxo-6,13-dioxatetracyclo[7.5.0.0^{1,5}.0^{2,12}]tetradecan-8-yl (2S)-2-hydroxy-2-methylbutanoate

> <ALOGPS_LOGP>
0.75

> <JCHEM_LOGP>
0.9449819380000003

> <ALOGPS_LOGS>
-2.61

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
10.940515503943253

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.661838089781932

> <JCHEM_PKA_STRONGEST_BASIC>
-3.655973333888027

> <JCHEM_POLAR_SURFACE_AREA>
148.82000000000002

> <JCHEM_REFRACTIVITY>
113.76489999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.17e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2R,3S,5R,8R,9S,10R,11R,12R)-11,12-dihydroxy-3,10-dimethyl-3-[(2S)-3-methyl-5-oxo-2H-furan-2-yl]-7-oxo-6,13-dioxatetracyclo[7.5.0.0^{1,5}.0^{2,12}]tetradecan-8-yl (2S)-2-hydroxy-2-methylbutanoate

> <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       0.146  -3.020   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.941  -2.195   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.714  -0.862   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.468   0.044   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.939  -0.583   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.100  -2.114   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -2.507  -2.741   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0      -1.128   0.946   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0      -0.302  -2.326   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       1.238  -2.326   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.944   1.508   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.484   1.508   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.960   0.044   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       4.366  -0.583   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       4.527  -2.114   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       5.934  -2.741   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       3.282  -3.020   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       3.497  -4.544   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       4.925  -5.120   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       6.138  -4.171   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       5.141  -6.645   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       5.356  -8.170   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       6.784  -8.746   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       6.666  -6.430   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       3.616  -6.861   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -0.457   2.149   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      -1.798   1.393   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      -2.932   2.436   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      -4.441   2.131   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      -2.291   3.836   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -0.761   3.659   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       0.281   4.792   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       0.767   3.038   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      -0.015  -4.551   0.000  0.00  0.00           C+0
CONECT    1    2    6   34                                                  
CONECT    2    1    3   17                                                  
CONECT    3    2    4   10   13                                             
CONECT    4    3    5   11                                                  
CONECT    5    4    6    8    9                                             
CONECT    6    5    1    7                                                  
CONECT    7    6                                                            
CONECT    8    5                                                            
CONECT    9    5   10                                                       
CONECT   10    9    3                                                       
CONECT   11    4   12   26   33                                             
CONECT   12   11   13                                                       
CONECT   13   12    3   14                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15    2   18                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22   24   25                                             
CONECT   22   21   23                                                       
CONECT   23   22                                                            
CONECT   24   21                                                            
CONECT   25   21                                                            
CONECT   26   11   27   31                                                  
CONECT   27   26   28                                                       
CONECT   28   27   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   31                                                       
CONECT   31   30   26   32                                                  
CONECT   32   31                                                            
CONECT   33   11                                                            
CONECT   34    1                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   76    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₄H₃₂O₁₀

Average Mass

480.5100 Da

Monoisotopic Mass

480.19955 Da

IUPAC Name

(1S,2R,3S,5R,8R,9S,10R,11R,12R)-11,12-dihydroxy-3,10-dimethyl-3-[(2S)-3-methyl-5-oxo-2,5-dihydrofuran-2-yl]-7-oxo-6,13-dioxatetracyclo[7.5.0.0^{1,5}.0^{2,12}]tetradecan-8-yl (2S)-2-hydroxy-2-methylbutanoate

Traditional Name

(1S,2R,3S,5R,8R,9S,10R,11R,12R)-11,12-dihydroxy-3,10-dimethyl-3-[(2S)-3-methyl-5-oxo-2H-furan-2-yl]-7-oxo-6,13-dioxatetracyclo[7.5.0.0^{1,5}.0^{2,12}]tetradecan-8-yl (2S)-2-hydroxy-2-methylbutanoate

CAS Registry Number

Not Available

SMILES

CC[C@](C)(O)C(=O)O[C@@H]1[C@H]2[C@@H](C)[C@@H](O)[C@]3(O)OC[C@]22[C@@H](C[C@](C)([C@H]4OC(=O)C=C4C)[C@@H]32)OC1=O

InChI Identifier

InChI=1S/C24H32O10/c1-6-22(5,29)20(28)34-15-14-11(3)16(26)24(30)19-21(4,17-10(2)7-13(25)33-17)8-12(32-18(15)27)23(14,19)9-31-24/h7,11-12,14-17,19,26,29-30H,6,8-9H2,1-5H3/t11-,12-,14-,15-,16-,17+,19-,21-,22+,23+,24+/m1/s1

InChI Key

OTNSHYRETRNONW-KIBZZZOKSA-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
Ailanthus altissima	LOTUS Database	35616633
Ailanthus altissimus	Plant	KNApSAcK
Ailanthus excelsa	LOTUS Database	35616633

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

Quassinoid
Tricarboxylic acid or derivatives
Delta valerolactone
Fatty acid ester
Delta_valerolactone
Oxepane
2-furanone
Oxane
Fatty acyl
Tetrahydrofuran
Tertiary alcohol
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Cyclic alcohol
Dihydrofuran
Secondary alcohol
Carboxylic acid ester
Hemiacetal
Lactone
Oxacycle
Carboxylic acid derivative
Organoheterocyclic compound
Organic oxide
Organic oxygen compound
Alcohol
Hydrocarbon derivative
Carbonyl group
Organooxygen 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	0.75	ALOGPS
logP	0.94	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Acidic)	7.66	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	148.82 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	113.76 m³·mol⁻¹	ChemAxon
Polarizability	47.07 Å³	ChemAxon
Number of Rings	5	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

C00031580

Chemspider ID

9071390

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10896127

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Tamura S, Fukamiya N, Okano M, Koyama J, Koike K, Tokuda H, Aoi W, Takayasu J, Kuchide M, Nishino H: Three new quassinoids, ailantinol E, F, and G, from Ailanthus altissima. Chem Pharm Bull (Tokyo). 2003 Apr;51(4):385-9. doi: 10.1248/cpb.51.385. [PubMed:12672989 ]

Showing NP-Card for (+)-Ailantinol G (NP0071953)

MOL for NP0071953 ((+)-Ailantinol G)

3D MOL for NP0071953 ((+)-Ailantinol G)

3D SDF for NP0071953 ((+)-Ailantinol G)

3D-SDF for NP0071953 ((+)-Ailantinol G)

PDB for NP0071953 ((+)-Ailantinol G)

3D PDB for NP0071953 ((+)-Ailantinol G)

SMILES for NP0071953 ((+)-Ailantinol G)

INCHI for NP0071953 ((+)-Ailantinol G)

Structure for NP0071953 ((+)-Ailantinol G)

3D Structure for NP0071953 ((+)-Ailantinol G)