NP-MRD: Showing NP-Card for 8',12'-dihydroxy-2,2,2',6',9',13'-hexamethyl-16'-methylidene-10',14'-dioxaspiro[pyran-3,5'-tetracyclo[7.6.1.0¹,¹².0²,⁷]hexadecan]-6'-ene-6,11',15'-trione (NP0199858)

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Record Information

Version

2.0

Created at

2022-09-04 18:34:39 UTC

Updated at

2022-09-04 18:34:40 UTC

NP-MRD ID

NP0199858

Secondary Accession Numbers

None

Natural Product Identification

Common Name

8',12'-dihydroxy-2,2,2',6',9',13'-hexamethyl-16'-methylidene-10',14'-dioxaspiro[pyran-3,5'-tetracyclo[7.6.1.0¹,¹².0²,⁷]hexadecan]-6'-ene-6,11',15'-trione

Description

Austinol belongs to the class of organic compounds known as furopyrans. These are organic polycyclic compounds containing a furan ring fused to a pyran ring. Furan is a five-membered aromatic ring with four carbon atoms and one oxygen atom. Pyran a six-membered heterocyclic, non-aromatic ring, made up of five carbon atoms and one oxygen atom and containing two double bonds. Austinol is an extremely weak basic (essentially neutral) compound (based on its pKa). 8',12'-dihydroxy-2,2,2',6',9',13'-hexamethyl-16'-methylidene-10',14'-dioxaspiro[pyran-3,5'-tetracyclo[7.6.1.0¹,¹².0²,⁷]hexadecan]-6'-ene-6,11',15'-trione is found in Aegiceras corniculatum, Aspergillus ustus and Penicillium simplicissimum. Metabolite of Emericella nidulans, Emericella dentata, Aspergillus variecolor and Aspergillus ustus.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 05061307502D          

 33 37  0  0  0  0            999 V2000
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    1.7541    0.5363    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.7100   -0.8075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7026   -1.1807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0898    0.1511    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9565    2.0007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0093    1.1417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1954    1.0070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

     RDKit          3D

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M  END


  Mrv0541 05061307502D          

 33 37  0  0  0  0            999 V2000
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M  END
> <DATABASE_ID>
NP0199858

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1OC(=O)C23C(=C)C(C)(OC(=O)C12O)C(O)C1=C(C)C2(CCC31C)C=CC(=O)OC2(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C25H30O8/c1-12-16-17(27)22(7)13(2)24(18(28)31-14(3)25(24,30)19(29)33-22)21(16,6)10-11-23(12)9-8-15(26)32-20(23,4)5/h8-9,14,17,27,30H,2,10-11H2,1,3-7H3

> <INCHI_KEY>
DNKFADXVMUNRRM-UHFFFAOYSA-N

> <FORMULA>
C25H30O8

> <MOLECULAR_WEIGHT>
458.5009

> <EXACT_MASS>
458.194067936

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
45.548013601963625

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
8',12'-dihydroxy-2,2,2',6',9',13'-hexamethyl-16'-methylidene-2,6-dihydro-10',14'-dioxaspiro[pyran-3,5'-tetracyclo[7.6.1.0¹,¹².0²,⁷]hexadecan]-6'-ene-6,11',15'-trione

> <ALOGPS_LOGP>
2.13

> <JCHEM_LOGP>
1.662103973333334

> <ALOGPS_LOGS>
-3.49

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.328454660557899

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.787206581508324

> <JCHEM_PKA_STRONGEST_BASIC>
-3.5307128875628324

> <JCHEM_POLAR_SURFACE_AREA>
119.36000000000001

> <JCHEM_REFRACTIVITY>
115.75819999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.50e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
8',12'-dihydroxy-2,2,2',6',9',13'-hexamethyl-16'-methylidene-10',14'-dioxaspiro[pyran-3,5'-tetracyclo[7.6.1.0¹,¹².0²,⁷]hexadecan]-6'-ene-6,11',15'-trione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       6.854   3.070   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.274   1.001   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.695  -2.908   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.925  -1.507   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.778  -2.204   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.768   0.282   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.786   3.735   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.351   2.131   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.831   1.880   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.228  -1.254   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.748  -1.003   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.312   1.629   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.600   0.640   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.708  -2.272   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      10.328   0.941   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.793   1.377   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.671   2.518   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.198  -2.000   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -0.083   0.424   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       8.267  -0.752   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.251  -0.064   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       2.076   2.222   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       7.290   0.438   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       2.630  -0.516   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       1.014  -0.759   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      11.847   1.193   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0       4.696  -2.358   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0      -1.595   0.133   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0      -0.468  -1.176   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0       2.051  -3.039   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0       4.134   3.987   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0       9.786  -0.500   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0       0.489   1.908   0.000  0.00  0.00           O+0
CONECT    1   12                                                            
CONECT    2   13                                                            
CONECT    3   14                                                            
CONECT    4   20                                                            
CONECT    5   20                                                            
CONECT    6   21                                                            
CONECT    7   22                                                            
CONECT    8    9   15                                                       
CONECT    9    8   23                                                       
CONECT   10   11   21                                                       
CONECT   11   10   23                                                       
CONECT   12    1   16   23                                                  
CONECT   13    2   22   24                                                  
CONECT   14    3   25   30                                                  
CONECT   15    8   26   32                                                  
CONECT   16   12   17   21                                                  
CONECT   17   16   22   31                                                  
CONECT   18   24   27   30                                                  
CONECT   19   25   28   33                                                  
CONECT   20    4    5   23   32                                             
CONECT   21    6   10   16   24                                             
CONECT   22    7   13   17   33                                             
CONECT   23    9   11   12   20                                             
CONECT   24   13   18   21   25                                             
CONECT   25   14   19   24   29                                             
CONECT   26   15                                                            
CONECT   27   18                                                            
CONECT   28   19                                                            
CONECT   29   25                                                            
CONECT   30   14   18                                                       
CONECT   31   17                                                            
CONECT   32   15   20                                                       
CONECT   33   19   22                                                       
MASTER        0    0    0    0    0    0    0    0   33    0   74    0
END

View in JSmol

Synonyms

Value	Source
Austinol	MeSH
Dehydroaustinol	MeSH

Chemical Formula

C₂₅H₃₀O₈

Average Mass

458.5009 Da

Monoisotopic Mass

458.19407 Da

IUPAC Name

8',12'-dihydroxy-2,2,2',6',9',13'-hexamethyl-16'-methylidene-2,6-dihydro-10',14'-dioxaspiro[pyran-3,5'-tetracyclo[7.6.1.0¹,¹².0²,⁷]hexadecan]-6'-ene-6,11',15'-trione

Traditional Name

8',12'-dihydroxy-2,2,2',6',9',13'-hexamethyl-16'-methylidene-10',14'-dioxaspiro[pyran-3,5'-tetracyclo[7.6.1.0¹,¹².0²,⁷]hexadecan]-6'-ene-6,11',15'-trione

CAS Registry Number

Not Available

SMILES

CC1OC(=O)C23C(=C)C(C)(OC(=O)C12O)C(O)C1=C(C)C2(CCC31C)C=CC(=O)OC2(C)C

InChI Identifier

InChI=1S/C25H30O8/c1-12-16-17(27)22(7)13(2)24(18(28)31-14(3)25(24,30)19(29)33-22)21(16,6)10-11-23(12)9-8-15(26)32-20(23,4)5/h8-9,14,17,27,30H,2,10-11H2,1,3-7H3

InChI Key

DNKFADXVMUNRRM-UHFFFAOYSA-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, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, 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
Aegiceras corniculatum	LOTUS Database	35616633
Aspergillus ustus	LOTUS Database	35616633
Penicillium simplicissimum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as furopyrans. These are organic polycyclic compounds containing a furan ring fused to a pyran ring. Furan is a five-membered aromatic ring with four carbon atoms and one oxygen atom. Pyran a six-membered heterocyclic, non-aromatic ring, made up of five carbon atoms and one oxygen atom and containing two double bonds.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Furopyrans

Sub Class

Not Available

Direct Parent

Furopyrans

Alternative Parents

Not Available

Substituents

Not Available

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	2.13	ALOGPS
logP	1.66	ChemAxon
logS	-3.5	ALOGPS
pKa (Strongest Acidic)	10.79	ChemAxon
pKa (Strongest Basic)	-3.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	119.36 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	115.76 m³·mol⁻¹	ChemAxon
Polarizability	45.55 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0034464

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB012873

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

73745644

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 8',12'-dihydroxy-2,2,2',6',9',13'-hexamethyl-16'-methylidene-10',14'-dioxaspiro[pyran-3,5'-tetracyclo[7.6.1.0¹,¹².0²,⁷]hexadecan]-6'-ene-6,11',15'-trione (NP0199858)

MOL for NP0199858 (8',12'-dihydroxy-2,2,2',6',9',13'-hexamethyl-16'-methylidene-10',14'-dioxaspiro[pyran-3,5'-tetracyclo[7.6.1.0¹,¹².0²,⁷]hexadecan]-6'-ene-6,11',15'-trione)

3D MOL for NP0199858 (8',12'-dihydroxy-2,2,2',6',9',13'-hexamethyl-16'-methylidene-10',14'-dioxaspiro[pyran-3,5'-tetracyclo[7.6.1.0¹,¹².0²,⁷]hexadecan]-6'-ene-6,11',15'-trione)

3D SDF for NP0199858 (8',12'-dihydroxy-2,2,2',6',9',13'-hexamethyl-16'-methylidene-10',14'-dioxaspiro[pyran-3,5'-tetracyclo[7.6.1.0¹,¹².0²,⁷]hexadecan]-6'-ene-6,11',15'-trione)

3D-SDF for NP0199858 (8',12'-dihydroxy-2,2,2',6',9',13'-hexamethyl-16'-methylidene-10',14'-dioxaspiro[pyran-3,5'-tetracyclo[7.6.1.0¹,¹².0²,⁷]hexadecan]-6'-ene-6,11',15'-trione)

PDB for NP0199858 (8',12'-dihydroxy-2,2,2',6',9',13'-hexamethyl-16'-methylidene-10',14'-dioxaspiro[pyran-3,5'-tetracyclo[7.6.1.0¹,¹².0²,⁷]hexadecan]-6'-ene-6,11',15'-trione)

3D PDB for NP0199858 (8',12'-dihydroxy-2,2,2',6',9',13'-hexamethyl-16'-methylidene-10',14'-dioxaspiro[pyran-3,5'-tetracyclo[7.6.1.0¹,¹².0²,⁷]hexadecan]-6'-ene-6,11',15'-trione)

SMILES for NP0199858 (8',12'-dihydroxy-2,2,2',6',9',13'-hexamethyl-16'-methylidene-10',14'-dioxaspiro[pyran-3,5'-tetracyclo[7.6.1.0¹,¹².0²,⁷]hexadecan]-6'-ene-6,11',15'-trione)

INCHI for NP0199858 (8',12'-dihydroxy-2,2,2',6',9',13'-hexamethyl-16'-methylidene-10',14'-dioxaspiro[pyran-3,5'-tetracyclo[7.6.1.0¹,¹².0²,⁷]hexadecan]-6'-ene-6,11',15'-trione)

Structure for NP0199858 (8',12'-dihydroxy-2,2,2',6',9',13'-hexamethyl-16'-methylidene-10',14'-dioxaspiro[pyran-3,5'-tetracyclo[7.6.1.0¹,¹².0²,⁷]hexadecan]-6'-ene-6,11',15'-trione)

3D Structure for NP0199858 (8',12'-dihydroxy-2,2,2',6',9',13'-hexamethyl-16'-methylidene-10',14'-dioxaspiro[pyran-3,5'-tetracyclo[7.6.1.0¹,¹².0²,⁷]hexadecan]-6'-ene-6,11',15'-trione)