NP-MRD: Showing NP-Card for Astraeusin O (NP0044169)

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Record Information

Version

2.0

Created at

2021-11-12 23:54:00 UTC

Updated at

2021-11-26 17:46:12 UTC

NP-MRD ID

NP0044169

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Astraeusin O

Description

Astraeusin O belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units. Astraeusin O is found in Astraeus asiaticus. Astraeusin O was first documented in 2017 (Masahiko Isaka et al.). Based on a literature review very few articles have been published on Astraeusin O.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652311132100542D          

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    9.0692   -0.9928    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2647   -2.4083    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
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  1  0  0  0  0
 19 22  1  0  0  0  0
 13 22  1  0  0  0  0
 22 23  1  1  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
  7 25  1  0  0  0  0
  2 26  1  6  0  0  0
 26 27  1  1  0  0  0
 26 28  1  0  0  0  0
 28 29  1  1  0  0  0
 28 30  1  0  0  0  0
 31 30  1  4  0  0  0
 31 32  2  0  0  0  0
 32 33  1  0  0  0  0
 32 34  1  0  0  0  0
 34 35  1  0  0  0  0
 34 36  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0044169

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C30H48O4/c1-18(26(33)34)8-10-23(31)19(2)20-12-16-30(7)22-9-11-24-27(3,4)25(32)14-15-28(24,5)21(22)13-17-29(20,30)6/h8,19-20,23-25,31-32H,9-17H2,1-7H3,(H,33,34)/t19-,20+,23-,24-,25+,28+,29+,30-/m0/s1

> <INCHI_KEY>
ZOAZKOJQEVTDKV-ASSAYMTPSA-N

> <FORMULA>
C30H48O4

> <MOLECULAR_WEIGHT>
472.71

> <EXACT_MASS>
472.355260026

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
82

> <JCHEM_AVERAGE_POLARIZABILITY>
57.01457608788744

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(5S,6S)-5-hydroxy-6-[(2S,5R,7R,11R,14R,15R)-5-hydroxy-2,6,6,11,15-pentamethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-1(10)-en-14-yl]-2-methylhept-2-enoic acid

> <ALOGPS_LOGP>
5.71

> <JCHEM_LOGP>
5.589600323000003

> <ALOGPS_LOGS>
-5.19

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
19.42328439632149

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.674449588214905

> <JCHEM_PKA_STRONGEST_BASIC>
-0.5335494565412987

> <JCHEM_POLAR_SURFACE_AREA>
77.76

> <JCHEM_REFRACTIVITY>
137.85440000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.07e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(5S,6S)-5-hydroxy-6-[(2S,5R,7R,11R,14R,15R)-5-hydroxy-2,6,6,11,15-pentamethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-1(10)-en-14-yl]-2-methylhept-2-enoic acid

> <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       0.810   2.218   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -0.521   2.992   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       1.341   3.664   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       2.326   1.947   0.000  0.00  0.00           C+0
HETATM   23  H   UNK     0       1.803   3.396   0.000  0.00  0.00           H+0
HETATM   24  C   UNK     0       3.319   3.125   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       4.835   2.854   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       9.882  -1.480   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       9.302  -2.907   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      11.407  -1.269   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      11.988   0.157   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      12.353  -2.485   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      13.878  -2.275   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      14.823  -3.490   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      14.243  -4.917   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      16.349  -3.280   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0      16.929  -1.853   0.000  0.00  0.00           O+0
HETATM   36  O   UNK     0      17.294  -4.496   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   11   26                                             
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6    7   11                                             
CONECT    6    5                                                            
CONECT    7    5    8   25                                                  
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   22                                             
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20   21   22                                             
CONECT   20   19                                                            
CONECT   21   19                                                            
CONECT   22   19   13   23   24                                             
CONECT   23   22                                                            
CONECT   24   22   25                                                       
CONECT   25   24    7                                                       
CONECT   26    2   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32   35   36                                                  
CONECT   35   34                                                            
CONECT   36   34                                                            
MASTER        0    0    0    0    0    0    0    0   36    0   78    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₀H₄₈O₄

Average Mass

472.7100 Da

Monoisotopic Mass

472.35526 Da

IUPAC Name

(5S,6S)-5-hydroxy-6-[(2S,5R,7R,11R,14R,15R)-5-hydroxy-2,6,6,11,15-pentamethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-1(10)-en-14-yl]-2-methylhept-2-enoic acid

Traditional Name

(5S,6S)-5-hydroxy-6-[(2S,5R,7R,11R,14R,15R)-5-hydroxy-2,6,6,11,15-pentamethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-1(10)-en-14-yl]-2-methylhept-2-enoic acid

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C30H48O4/c1-18(26(33)34)8-10-23(31)19(2)20-12-16-30(7)22-9-11-24-27(3,4)25(32)14-15-28(24,5)21(22)13-17-29(20,30)6/h8,19-20,23-25,31-32H,9-17H2,1-7H3,(H,33,34)/t19-,20+,23-,24-,25+,28+,29+,30-/m0/s1

InChI Key

ZOAZKOJQEVTDKV-ASSAYMTPSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 150 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 250 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 175 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 225 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 125 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, Dimethylsulfoxide-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 triterpenoids. These are terpene molecules containing six isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Triterpenoids

Direct Parent

Triterpenoids

Alternative Parents

Substituents

Triterpenoid
Dihydroxy bile acid, alcohol, or derivatives
Hydroxy bile acid, alcohol, or derivatives
Bile acid, alcohol, or derivatives
22-hydroxysteroid
Steroid acid
3-hydroxysteroid
14-alpha-methylsteroid
3-alpha-hydroxysteroid
Hydroxysteroid
Steroid
Medium-chain fatty acid
Hydroxy fatty acid
Fatty acyl
Fatty acid
Unsaturated fatty acid
Cyclic alcohol
Secondary alcohol
Carboxylic acid
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Organooxygen compound
Hydrocarbon derivative
Organic oxygen compound
Carbonyl group
Organic oxide
Alcohol
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic 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	5.71	ALOGPS
logP	5.59	ChemAxon
logS	-5.2	ALOGPS
pKa (Strongest Acidic)	4.67	ChemAxon
pKa (Strongest Basic)	-0.53	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	77.76 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	137.85 m³·mol⁻¹	ChemAxon
Polarizability	57.01 Å³	ChemAxon
Number of Rings	4	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

78439159

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

139590186

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 O (NP0044169)

MOL for NP0044169 (Astraeusin O)

3D MOL for NP0044169 (Astraeusin O)

3D SDF for NP0044169 (Astraeusin O)

3D-SDF for NP0044169 (Astraeusin O)

PDB for NP0044169 (Astraeusin O)

3D PDB for NP0044169 (Astraeusin O)

SMILES for NP0044169 (Astraeusin O)

INCHI for NP0044169 (Astraeusin O)

Structure for NP0044169 (Astraeusin O)

3D Structure for NP0044169 (Astraeusin O)