NP-MRD: Showing NP-Card for Astraeusin Q (NP0044171)

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Record Information

Version

1.0

Created at

2021-11-12 23:54:05 UTC

Updated at

2021-11-26 17:46:13 UTC

NP-MRD ID

NP0044171

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Astraeusin Q

Description

Astraeusin Q belongs to the class of organic compounds known as withanolides and derivatives. These are c28 steroids structurally characterized by an ergostane skeleton usually functionalized at carbons 1, 22 and 26 to form a lactone ring. Astraeusin Q is found in Astraeus asiaticus. It was first documented in 2017 (Masahiko Isaka et al.). Based on a literature review very few articles have been published on Astraeusin Q.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652311132100542D          

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M  END

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M  END


  Mrv1652311132100542D          

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    1.2463    1.0432    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9660    1.8191    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7781    1.6739    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5902    1.5287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2939   -0.7929    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.1111   -0.6800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9830   -1.5571    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.8002   -1.4442    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4893   -2.2084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1784   -2.9726    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3612   -3.0854    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.0503   -3.8496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8548   -2.4341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0376   -2.5469    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1657   -1.6699    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1  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  1  0  0  0
  5  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
  2 11  1  0  0  0  0
  5 11  1  0  0  0  0
 11 12  1  6  0  0  0
  8 13  1  0  0  0  0
 13 14  1  6  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  1  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  2  0  0  0  0
 17 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  1  0  0  0  0
 22 25  1  0  0  0  0
 13 25  1  0  0  0  0
 25 26  1  1  0  0  0
 25 27  1  0  0  0  0
 27 28  1  0  0  0  0
  7 28  1  0  0  0  0
  2 29  1  6  0  0  0
 29 30  1  6  0  0  0
 31 29  1  6  0  0  0
 31 32  1  1  0  0  0
 31 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  1  0  0  0
 35 37  1  0  0  0  0
 37 38  2  0  0  0  0
 37 39  1  0  0  0  0
 31 39  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0044171

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@@]1(CC[C@@]2(C)C3=C(CC[C@]12C)[C@@]1(C)CC[C@@H](OC(C)=O)C(C)(C)[C@]1([H])CC3)[C@H](C)[C@]1([H])CC[C@@H](C)C(=O)O1

> <INCHI_IDENTIFIER>
InChI=1S/C32H50O4/c1-19-9-11-25(36-28(19)34)20(2)22-13-17-32(8)24-10-12-26-29(4,5)27(35-21(3)33)15-16-30(26,6)23(24)14-18-31(22,32)7/h19-20,22,25-27H,9-18H2,1-8H3/t19-,20+,22-,25+,26+,27-,30-,31-,32+/m1/s1

> <INCHI_KEY>
IPISRXBXIKQSBU-BQNFLXHXSA-N

> <FORMULA>
C32H50O4

> <MOLECULAR_WEIGHT>
498.748

> <EXACT_MASS>
498.37091009

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
86

> <JCHEM_AVERAGE_POLARIZABILITY>
60.29385213988139

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S,5R,7R,11R,14R,15R)-2,6,6,11,15-pentamethyl-14-[(1S)-1-[(2S,5R)-5-methyl-6-oxooxan-2-yl]ethyl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-1(10)-en-5-yl acetate

> <ALOGPS_LOGP>
6.81

> <JCHEM_LOGP>
6.844809157333332

> <ALOGPS_LOGS>
-5.96

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-6.738264509368373

> <JCHEM_POLAR_SURFACE_AREA>
52.60000000000001

> <JCHEM_REFRACTIVITY>
142.6378

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
5.47e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S,5R,7R,11R,14R,15R)-2,6,6,11,15-pentamethyl-14-[(1S)-1-[(2S,5R)-5-methyl-6-oxooxan-2-yl]ethyl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-1(10)-en-5-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 13-NOV-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   13-NOV-21         0                                  
HETATM    1  H   UNK     0      10.449   0.026   0.000  0.00  0.00           H+0
HETATM    2  C   UNK     0       8.937  -0.264   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       9.365   1.215   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.090   2.079   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.874   1.134   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.505   2.629   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.358   1.405   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.366   0.228   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.889  -1.221   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.405  -1.492   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.398  -0.314   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.069  -1.700   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.850   0.499   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.373  -0.949   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.857  -0.678   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.341  -0.407   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -0.182   1.041   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -1.698   1.312   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      -2.221   2.761   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -3.737   3.032   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      -1.229   3.938   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       0.810   2.218   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -0.521   2.992   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       1.341   3.664   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       2.326   1.947   0.000  0.00  0.00           C+0
HETATM   26  H   UNK     0       1.803   3.396   0.000  0.00  0.00           H+0
HETATM   27  C   UNK     0       3.319   3.125   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       4.835   2.854   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       9.882  -1.480   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      11.407  -1.269   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       9.302  -2.907   0.000  0.00  0.00           C+0
HETATM   32  H   UNK     0      10.827  -2.696   0.000  0.00  0.00           H+0
HETATM   33  C   UNK     0      10.247  -4.122   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       9.666  -5.549   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       8.141  -5.759   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       7.561  -7.186   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       7.196  -4.544   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0       5.670  -4.754   0.000  0.00  0.00           O+0
HETATM   39  O   UNK     0       7.776  -3.117   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   11   29                                             
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6    7   11                                             
CONECT    6    5                                                            
CONECT    7    5    8   28                                                  
CONECT    8    7    9   13                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10    2    5   12                                             
CONECT   12   11                                                            
CONECT   13    8   14   15   25                                             
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   22                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19                                                            
CONECT   22   17   23   24   25                                             
CONECT   23   22                                                            
CONECT   24   22                                                            
CONECT   25   22   13   26   27                                             
CONECT   26   25                                                            
CONECT   27   25   28                                                       
CONECT   28   27    7                                                       
CONECT   29    2   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   32   33   39                                             
CONECT   32   31                                                            
CONECT   33   31   34                                                       
CONECT   34   33   35                                                       
CONECT   35   34   36   37                                                  
CONECT   36   35                                                            
CONECT   37   35   38   39                                                  
CONECT   38   37                                                            
CONECT   39   37   31                                                       
MASTER        0    0    0    0    0    0    0    0   39    0   86    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₂H₅₀O₄

Average Mass

498.7480 Da

Monoisotopic Mass

498.37091 Da

IUPAC Name

(2S,5R,7R,11R,14R,15R)-2,6,6,11,15-pentamethyl-14-[(1S)-1-[(2S,5R)-5-methyl-6-oxooxan-2-yl]ethyl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-1(10)-en-5-yl acetate

Traditional Name

(2S,5R,7R,11R,14R,15R)-2,6,6,11,15-pentamethyl-14-[(1S)-1-[(2S,5R)-5-methyl-6-oxooxan-2-yl]ethyl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-1(10)-en-5-yl acetate

CAS Registry Number

Not Available

SMILES

[H][C@@]1(CC[C@@]2(C)C3=C(CC[C@]12C)[C@@]1(C)CC[C@@H](OC(C)=O)C(C)(C)[C@]1([H])CC3)[C@H](C)[C@]1([H])CC[C@@H](C)C(=O)O1

InChI Identifier

InChI=1S/C32H50O4/c1-19-9-11-25(36-28(19)34)20(2)22-13-17-32(8)24-10-12-26-29(4,5)27(35-21(3)33)15-16-30(26,6)23(24)14-18-31(22,32)7/h19-20,22,25-27H,9-18H2,1-8H3/t19-,20+,22-,25+,26+,27-,30-,31-,32+/m1/s1

InChI Key

IPISRXBXIKQSBU-BQNFLXHXSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, Acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 150 MHz, Acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 250 MHz, Acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 175 MHz, Acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, Acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, Acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 225 MHz, Acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, Acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 125 MHz, Acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, Acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Astraeus asiaticus	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as withanolides and derivatives. These are c28 steroids structurally characterized by an ergostane skeleton usually functionalized at carbons 1, 22 and 26 to form a lactone ring.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Steroid lactones

Direct Parent

Withanolides and derivatives

Alternative Parents

Substituents

Triterpenoid
Withanolide-skeleton
Steroid ester
14-alpha-methylsteroid
Delta_valerolactone
Delta valerolactone
Oxane
Dicarboxylic acid or derivatives
Lactone
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
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	6.81	ALOGPS
logP	6.84	ChemAxon
logS	-6	ALOGPS
pKa (Strongest Basic)	-6.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	52.6 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	142.64 m³·mol⁻¹	ChemAxon
Polarizability	60.29 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

78439161

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

139590188

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Masahiko Isaka et al. (2017). Lanostane triterpenoids from the edible mushroom Astraeus asiaticus. Tetrahedron, 73(12), 1561-1567 - March 2017. DOI: 10.1016/j.tet.2017.01.070. Tetrahedron.

Showing NP-Card for Astraeusin Q (NP0044171)

MOL for NP0044171 (Astraeusin Q)

3D MOL for NP0044171 (Astraeusin Q)

3D SDF for NP0044171 (Astraeusin Q)

3D-SDF for NP0044171 (Astraeusin Q)

PDB for NP0044171 (Astraeusin Q)

3D PDB for NP0044171 (Astraeusin Q)

SMILES for NP0044171 (Astraeusin Q)

INCHI for NP0044171 (Astraeusin Q)

Structure for NP0044171 (Astraeusin Q)

3D Structure for NP0044171 (Astraeusin Q)