NP-MRD: Showing NP-Card for 14-hydroxy-2,6,6,13,16,19-hexamethyl-7,15,17,20-tetraoxaspiro[heptacyclo[11.8.1.0¹,¹⁸.0²,¹¹.0⁵,¹⁰.0¹¹,¹⁶.0¹⁴,¹⁸]docosane-22,2'-oxirane]-4,9-diene-8,21-dione (NP0221022)

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Record Information

Version

2.0

Created at

2022-09-05 22:29:38 UTC

Updated at

2022-09-05 22:29:38 UTC

NP-MRD ID

NP0221022

Secondary Accession Numbers

None

Natural Product Identification

Common Name

14-hydroxy-2,6,6,13,16,19-hexamethyl-7,15,17,20-tetraoxaspiro[heptacyclo[11.8.1.0¹,¹⁸.0²,¹¹.0⁵,¹⁰.0¹¹,¹⁶.0¹⁴,¹⁸]docosane-22,2'-oxirane]-4,9-diene-8,21-dione

Description

14-Hydroxy-2,6,6,13,16,19-hexamethyl-7,15,17,20-tetraoxaspiro[heptacyclo[11.8.1.0¹,¹⁸.0²,¹¹.0⁵,¹⁰.0¹¹,¹⁶.0¹⁴,¹⁸]Docosane-22,2'-oxirane]-4,9-diene-8,21-dione belongs to the class of organic compounds known as naphthopyrans. Naphthopyrans are compounds containing a pyran ring fused to a naphthalene moiety. Furan is a 6 membered-ring non-aromatic ring with five carbon and one oxygen atoms. Naphthalene is a polycyclic aromatic hydrocarbon made up of two fused benzene rings. 14-hydroxy-2,6,6,13,16,19-hexamethyl-7,15,17,20-tetraoxaspiro[heptacyclo[11.8.1.0¹,¹⁸.0²,¹¹.0⁵,¹⁰.0¹¹,¹⁶.0¹⁴,¹⁸]docosane-22,2'-oxirane]-4,9-diene-8,21-dione is found in Talaromyces purpureogenus. Based on a literature review very few articles have been published on 14-hydroxy-2,6,6,13,16,19-hexamethyl-7,15,17,20-tetraoxaspiro[heptacyclo[11.8.1.0¹,¹⁸.0²,¹¹.0⁵,¹⁰.0¹¹,¹⁶.0¹⁴,¹⁸]Docosane-22,2'-oxirane]-4,9-diene-8,21-dione.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309062200292D          

 33 40  0  0  0  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652309062200292D          

 33 40  0  0  0  0            999 V2000
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M  END
> <DATABASE_ID>
NP0221022

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1OC(=O)C23C4(CO4)C4(C)CC5(C6=CC(=O)OC(C)(C)C6=CCC25C)C2(C)OC4(O)C13O2

> <INCHI_IDENTIFIER>
InChI=1S/C25H28O8/c1-12-24-23(16(27)30-12)18(4)8-7-13-14(9-15(26)31-17(13,2)3)21(18)10-19(5,22(23)11-29-22)25(24,28)33-20(21,6)32-24/h7,9,12,28H,8,10-11H2,1-6H3

> <INCHI_KEY>
HKYMRYMDXIHYTJ-UHFFFAOYSA-N

> <FORMULA>
C25H28O8

> <MOLECULAR_WEIGHT>
456.491

> <EXACT_MASS>
456.178417862

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
61

> <JCHEM_AVERAGE_POLARIZABILITY>
45.26878683978061

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
14-hydroxy-2,6,6,13,16,19-hexamethyl-7,15,17,20-tetraoxaspiro[heptacyclo[11.8.1.0^{1,18}.0^{2,11}.0^{5,10}.0^{11,16}.0^{14,18}]docosane-22,2'-oxirane]-4,9-diene-8,21-dione

> <JCHEM_LOGP>
1.952354284000001

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
8

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.412359961864441

> <JCHEM_PKA_STRONGEST_BASIC>
-3.9110083376877083

> <JCHEM_POLAR_SURFACE_AREA>
103.82000000000002

> <JCHEM_REFRACTIVITY>
111.5337

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
14-hydroxy-2,6,6,13,16,19-hexamethyl-7,15,17,20-tetraoxaspiro[heptacyclo[11.8.1.0^{1,18}.0^{2,11}.0^{5,10}.0^{11,16}.0^{14,18}]docosane-22,2'-oxirane]-4,9-diene-8,21-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-SEP-22         0                                  
HETATM    1  C   UNK     0      -0.288  -0.956   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.809   0.125   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       0.319   1.585   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       1.758   2.105   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       2.019   3.623   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       2.975   1.105   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.544   1.581   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.082   1.650   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.082   3.115   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.596   3.507   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.485   2.218   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.753   0.862   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.561  -0.449   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.100  -0.405   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       9.908  -1.716   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       9.832   0.950   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       9.024   2.261   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      10.306   3.114   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       9.034   3.801   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.270  -0.014   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       6.391  -1.126   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.913  -1.505   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       5.225  -3.014   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       3.172  -1.780   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       1.814  -2.506   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0       3.756  -3.136   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       3.972  -1.397   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       3.151  -0.094   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       2.193  -1.961   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       2.272  -0.389   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       3.989  -0.099   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       3.830   1.433   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       5.236   0.805   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   30                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7   30   31                                             
CONECT    7    6    8    9   20                                             
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   17                                                  
CONECT   12   11   13   20                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17                                                       
CONECT   17   16   11   18   19                                             
CONECT   18   17                                                            
CONECT   19   17                                                            
CONECT   20   12    7   21   27                                             
CONECT   21   20   22                                                       
CONECT   22   21   23   24   31                                             
CONECT   23   22                                                            
CONECT   24   22   25   26   30                                             
CONECT   25   24                                                            
CONECT   26   24   27                                                       
CONECT   27   26   20   28   29                                             
CONECT   28   27                                                            
CONECT   29   27   30                                                       
CONECT   30   29    2   24    6                                             
CONECT   31   22    6   32   33                                             
CONECT   32   31   33                                                       
CONECT   33   32   31                                                       
MASTER        0    0    0    0    0    0    0    0   33    0   80    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₅H₂₈O₈

Average Mass

456.4910 Da

Monoisotopic Mass

456.17842 Da

IUPAC Name

14-hydroxy-2,6,6,13,16,19-hexamethyl-7,15,17,20-tetraoxaspiro[heptacyclo[11.8.1.0^{1,18}.0^{2,11}.0^{5,10}.0^{11,16}.0^{14,18}]docosane-22,2'-oxirane]-4,9-diene-8,21-dione

Traditional Name

14-hydroxy-2,6,6,13,16,19-hexamethyl-7,15,17,20-tetraoxaspiro[heptacyclo[11.8.1.0^{1,18}.0^{2,11}.0^{5,10}.0^{11,16}.0^{14,18}]docosane-22,2'-oxirane]-4,9-diene-8,21-dione

CAS Registry Number

Not Available

SMILES

CC1OC(=O)C23C4(CO4)C4(C)CC5(C6=CC(=O)OC(C)(C)C6=CCC25C)C2(C)OC4(O)C13O2

InChI Identifier

InChI=1S/C25H28O8/c1-12-24-23(16(27)30-12)18(4)8-7-13-14(9-15(26)31-17(13,2)3)21(18)10-19(5,22(23)11-29-22)25(24,28)33-20(21,6)32-24/h7,9,12,28H,8,10-11H2,1-6H3

InChI Key

HKYMRYMDXIHYTJ-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
Penicillium purpurogenum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as naphthopyrans. Naphthopyrans are compounds containing a pyran ring fused to a naphthalene moiety. Furan is a 6 membered-ring non-aromatic ring with five carbon and one oxygen atoms. Naphthalene is a polycyclic aromatic hydrocarbon made up of two fused benzene rings.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Naphthopyrans

Sub Class

Not Available

Direct Parent

Naphthopyrans

Alternative Parents

Substituents

Naphthopyran
Naphthalene
Furopyran
Ketal
Dihydropyranone
Oxepane
Dicarboxylic acid or derivatives
Pyran
Oxane
Gamma butyrolactone
Meta-dioxolane
Cyclic alcohol
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Tetrahydrofuran
Furan
Carboxylic acid ester
Lactone
Hemiacetal
Ether
Oxirane
Oxacycle
Dialkyl ether
Carboxylic acid derivative
Acetal
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
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	1.95	ChemAxon
pKa (Strongest Acidic)	10.41	ChemAxon
pKa (Strongest Basic)	-3.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	103.82 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	111.53 m³·mol⁻¹	ChemAxon
Polarizability	45.27 Å³	ChemAxon
Number of Rings	8	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

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

163049498

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 14-hydroxy-2,6,6,13,16,19-hexamethyl-7,15,17,20-tetraoxaspiro[heptacyclo[11.8.1.0¹,¹⁸.0²,¹¹.0⁵,¹⁰.0¹¹,¹⁶.0¹⁴,¹⁸]docosane-22,2'-oxirane]-4,9-diene-8,21-dione (NP0221022)

MOL for NP0221022 (14-hydroxy-2,6,6,13,16,19-hexamethyl-7,15,17,20-tetraoxaspiro[heptacyclo[11.8.1.0¹,¹⁸.0²,¹¹.0⁵,¹⁰.0¹¹,¹⁶.0¹⁴,¹⁸]docosane-22,2'-oxirane]-4,9-diene-8,21-dione)

3D MOL for NP0221022 (14-hydroxy-2,6,6,13,16,19-hexamethyl-7,15,17,20-tetraoxaspiro[heptacyclo[11.8.1.0¹,¹⁸.0²,¹¹.0⁵,¹⁰.0¹¹,¹⁶.0¹⁴,¹⁸]docosane-22,2'-oxirane]-4,9-diene-8,21-dione)

3D SDF for NP0221022 (14-hydroxy-2,6,6,13,16,19-hexamethyl-7,15,17,20-tetraoxaspiro[heptacyclo[11.8.1.0¹,¹⁸.0²,¹¹.0⁵,¹⁰.0¹¹,¹⁶.0¹⁴,¹⁸]docosane-22,2'-oxirane]-4,9-diene-8,21-dione)

3D-SDF for NP0221022 (14-hydroxy-2,6,6,13,16,19-hexamethyl-7,15,17,20-tetraoxaspiro[heptacyclo[11.8.1.0¹,¹⁸.0²,¹¹.0⁵,¹⁰.0¹¹,¹⁶.0¹⁴,¹⁸]docosane-22,2'-oxirane]-4,9-diene-8,21-dione)

PDB for NP0221022 (14-hydroxy-2,6,6,13,16,19-hexamethyl-7,15,17,20-tetraoxaspiro[heptacyclo[11.8.1.0¹,¹⁸.0²,¹¹.0⁵,¹⁰.0¹¹,¹⁶.0¹⁴,¹⁸]docosane-22,2'-oxirane]-4,9-diene-8,21-dione)

3D PDB for NP0221022 (14-hydroxy-2,6,6,13,16,19-hexamethyl-7,15,17,20-tetraoxaspiro[heptacyclo[11.8.1.0¹,¹⁸.0²,¹¹.0⁵,¹⁰.0¹¹,¹⁶.0¹⁴,¹⁸]docosane-22,2'-oxirane]-4,9-diene-8,21-dione)

SMILES for NP0221022 (14-hydroxy-2,6,6,13,16,19-hexamethyl-7,15,17,20-tetraoxaspiro[heptacyclo[11.8.1.0¹,¹⁸.0²,¹¹.0⁵,¹⁰.0¹¹,¹⁶.0¹⁴,¹⁸]docosane-22,2'-oxirane]-4,9-diene-8,21-dione)

INCHI for NP0221022 (14-hydroxy-2,6,6,13,16,19-hexamethyl-7,15,17,20-tetraoxaspiro[heptacyclo[11.8.1.0¹,¹⁸.0²,¹¹.0⁵,¹⁰.0¹¹,¹⁶.0¹⁴,¹⁸]docosane-22,2'-oxirane]-4,9-diene-8,21-dione)

Structure for NP0221022 (14-hydroxy-2,6,6,13,16,19-hexamethyl-7,15,17,20-tetraoxaspiro[heptacyclo[11.8.1.0¹,¹⁸.0²,¹¹.0⁵,¹⁰.0¹¹,¹⁶.0¹⁴,¹⁸]docosane-22,2'-oxirane]-4,9-diene-8,21-dione)

3D Structure for NP0221022 (14-hydroxy-2,6,6,13,16,19-hexamethyl-7,15,17,20-tetraoxaspiro[heptacyclo[11.8.1.0¹,¹⁸.0²,¹¹.0⁵,¹⁰.0¹¹,¹⁶.0¹⁴,¹⁸]docosane-22,2'-oxirane]-4,9-diene-8,21-dione)