NP-MRD: Showing NP-Card for 5'-methoxy-4,5,5,6',10',12'-hexamethyl-14'-oxaspiro[oxolane-2,13'-tetracyclo[9.3.2.0¹,¹⁰.0²,⁷]hexadecane]-2',4',6'-triene-3,8'-diol (NP0279745)

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Record Information

Version

2.0

Created at

2022-09-09 05:14:48 UTC

Updated at

2022-09-09 05:14:48 UTC

NP-MRD ID

NP0279745

Secondary Accession Numbers

None

Natural Product Identification

Common Name

5'-methoxy-4,5,5,6',10',12'-hexamethyl-14'-oxaspiro[oxolane-2,13'-tetracyclo[9.3.2.0¹,¹⁰.0²,⁷]hexadecane]-2',4',6'-triene-3,8'-diol

Description

5'-Methoxy-4,5,5,6',10',12'-hexamethyl-14'-oxaspiro[oxolane-2,13'-tetracyclo[9.3.2.0¹,¹⁰.0²,⁷]Hexadecane]-2'(7'),3',5'-triene-3,8'-diol 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. 5'-methoxy-4,5,5,6',10',12'-hexamethyl-14'-oxaspiro[oxolane-2,13'-tetracyclo[9.3.2.0¹,¹⁰.0²,⁷]hexadecane]-2',4',6'-triene-3,8'-diol is found in Agaricus blazei. 5'-Methoxy-4,5,5,6',10',12'-hexamethyl-14'-oxaspiro[oxolane-2,13'-tetracyclo[9.3.2.0¹,¹⁰.0²,⁷]Hexadecane]-2'(7'),3',5'-triene-3,8'-diol is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004191523542D          

 30 34  0  0  0  0            999 V2000
    5.5132   -0.3392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9812    0.2913    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1691    0.1459    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8891   -0.6301    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0770   -0.7756    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5450   -0.1450    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8250    0.6310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2930    1.2615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5731    2.0375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3645    1.1235    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2009    0.3401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7182   -0.3290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3136    0.6945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3534   -0.1296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0225   -0.6123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7329   -0.2905    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1387    0.3695    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7453    1.0947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4878    1.8785    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1536    2.3656    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5995    2.9769    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7036    2.9806    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8227    1.8829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6064    2.1405    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5703    1.0975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0575    0.4317    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9331    1.2393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7110    2.0339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6371    0.7764    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9172    1.5524    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
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 11 13  1  0  0  0  0
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  6 16  1  0  0  0  0
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  7 29  2  0  0  0  0
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M  END

     RDKit          3D

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   -2.5220    2.3742    0.8970 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1533004191523542D          

 30 34  0  0  0  0            999 V2000
    5.5132   -0.3392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9812    0.2913    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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M  END
> <DATABASE_ID>
NP0279745

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC=C2C(C(O)CC3(C)C4CCC23OC2(OC(C)(C)C(C)C2O)C4C)=C1C

> <INCHI_IDENTIFIER>
InChI=1S/C25H36O5/c1-13-19(28-7)9-8-17-20(13)18(26)12-23(6)16-10-11-24(17,23)30-25(14(16)2)21(27)15(3)22(4,5)29-25/h8-9,14-16,18,21,26-27H,10-12H2,1-7H3

> <INCHI_KEY>
MZTFHKCGOTZMAW-UHFFFAOYSA-N

> <FORMULA>
C25H36O5

> <MOLECULAR_WEIGHT>
416.558

> <EXACT_MASS>
416.256274259

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
66

> <JCHEM_AVERAGE_POLARIZABILITY>
46.66953849303403

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5'-methoxy-4,5,5,6',10',12'-hexamethyl-14'-oxaspiro[oxolane-2,13'-tetracyclo[9.3.2.0¹,¹⁰.0²,⁷]hexadecane]-2',4',6'-triene-3,8'-diol

> <ALOGPS_LOGP>
3.73

> <JCHEM_LOGP>
4.056994296999999

> <ALOGPS_LOGS>
-4.97

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.352550026092256

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.941009507374037

> <JCHEM_PKA_STRONGEST_BASIC>
-3.0898301143765794

> <JCHEM_POLAR_SURFACE_AREA>
68.15

> <JCHEM_REFRACTIVITY>
114.6213

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.48e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5'-methoxy-4,5,5,6',10',12'-hexamethyl-14'-oxaspiro[oxolane-2,13'-tetracyclo[9.3.2.0¹,¹⁰.0²,⁷]hexadecane]-2',4',6'-triene-3,8'-diol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 19-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-APR-15         0                                  
HETATM    1  C   UNK     0      10.291  -0.633   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       9.298   0.544   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       7.782   0.272   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.260  -1.176   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.744  -1.448   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.751  -0.271   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.273   1.178   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.280   2.355   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       4.803   3.803   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       2.547   2.097   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.242   0.635   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.341  -0.614   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.585   1.296   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.660  -0.242   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.909  -1.143   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.235  -0.542   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       3.992   0.690   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       3.258   2.043   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       2.777   3.507   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       4.020   4.416   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.986   5.557   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       5.047   5.564   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       5.269   3.515   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       6.732   3.996   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       4.798   2.049   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       5.707   0.806   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       1.742   2.313   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       1.327   3.797   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       6.789   1.449   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       7.312   2.898   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   29                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   16                                                  
CONECT    7    6    8   29                                                  
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10   12   13   16                                             
CONECT   12   11                                                            
CONECT   13   11   14   27                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15    6   11   17                                             
CONECT   17   16   18                                                       
CONECT   18   17   19   25   27                                             
CONECT   19   18   20                                                       
CONECT   20   19   21   22   23                                             
CONECT   21   20                                                            
CONECT   22   20                                                            
CONECT   23   20   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   18   26                                                  
CONECT   26   25                                                            
CONECT   27   18   13   28                                                  
CONECT   28   27                                                            
CONECT   29    7    3   30                                                  
CONECT   30   29                                                            
MASTER        0    0    0    0    0    0    0    0   30    0   68    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₅H₃₆O₅

Average Mass

416.5580 Da

Monoisotopic Mass

416.25627 Da

IUPAC Name

5'-methoxy-4,5,5,6',10',12'-hexamethyl-14'-oxaspiro[oxolane-2,13'-tetracyclo[9.3.2.0¹,¹⁰.0²,⁷]hexadecane]-2',4',6'-triene-3,8'-diol

Traditional Name

5'-methoxy-4,5,5,6',10',12'-hexamethyl-14'-oxaspiro[oxolane-2,13'-tetracyclo[9.3.2.0¹,¹⁰.0²,⁷]hexadecane]-2',4',6'-triene-3,8'-diol

CAS Registry Number

Not Available

SMILES

COC1=CC=C2C(C(O)CC3(C)C4CCC23OC2(OC(C)(C)C(C)C2O)C4C)=C1C

InChI Identifier

InChI=1S/C25H36O5/c1-13-19(28-7)9-8-17-20(13)18(26)12-23(6)16-10-11-24(17,23)30-25(14(16)2)21(27)15(3)22(4,5)29-25/h8-9,14-16,18,21,26-27H,10-12H2,1-7H3

InChI Key

MZTFHKCGOTZMAW-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
Agaricus blazei	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
Tetralin
Anisole
Alkyl aryl ether
Ketal
Oxepane
Benzenoid
Oxane
Pyran
Oxolane
Secondary alcohol
Acetal
Oxacycle
Ether
Alcohol
Organooxygen compound
Hydrocarbon derivative
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic 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	3.73	ALOGPS
logP	4.06	ChemAxon
logS	-5	ALOGPS
pKa (Strongest Acidic)	12.94	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	68.15 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	114.62 m³·mol⁻¹	ChemAxon
Polarizability	46.67 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

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

57406061

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 5'-methoxy-4,5,5,6',10',12'-hexamethyl-14'-oxaspiro[oxolane-2,13'-tetracyclo[9.3.2.0¹,¹⁰.0²,⁷]hexadecane]-2',4',6'-triene-3,8'-diol (NP0279745)

MOL for NP0279745 (5'-methoxy-4,5,5,6',10',12'-hexamethyl-14'-oxaspiro[oxolane-2,13'-tetracyclo[9.3.2.0¹,¹⁰.0²,⁷]hexadecane]-2',4',6'-triene-3,8'-diol)

3D MOL for NP0279745 (5'-methoxy-4,5,5,6',10',12'-hexamethyl-14'-oxaspiro[oxolane-2,13'-tetracyclo[9.3.2.0¹,¹⁰.0²,⁷]hexadecane]-2',4',6'-triene-3,8'-diol)

3D SDF for NP0279745 (5'-methoxy-4,5,5,6',10',12'-hexamethyl-14'-oxaspiro[oxolane-2,13'-tetracyclo[9.3.2.0¹,¹⁰.0²,⁷]hexadecane]-2',4',6'-triene-3,8'-diol)

3D-SDF for NP0279745 (5'-methoxy-4,5,5,6',10',12'-hexamethyl-14'-oxaspiro[oxolane-2,13'-tetracyclo[9.3.2.0¹,¹⁰.0²,⁷]hexadecane]-2',4',6'-triene-3,8'-diol)

PDB for NP0279745 (5'-methoxy-4,5,5,6',10',12'-hexamethyl-14'-oxaspiro[oxolane-2,13'-tetracyclo[9.3.2.0¹,¹⁰.0²,⁷]hexadecane]-2',4',6'-triene-3,8'-diol)

3D PDB for NP0279745 (5'-methoxy-4,5,5,6',10',12'-hexamethyl-14'-oxaspiro[oxolane-2,13'-tetracyclo[9.3.2.0¹,¹⁰.0²,⁷]hexadecane]-2',4',6'-triene-3,8'-diol)

SMILES for NP0279745 (5'-methoxy-4,5,5,6',10',12'-hexamethyl-14'-oxaspiro[oxolane-2,13'-tetracyclo[9.3.2.0¹,¹⁰.0²,⁷]hexadecane]-2',4',6'-triene-3,8'-diol)

INCHI for NP0279745 (5'-methoxy-4,5,5,6',10',12'-hexamethyl-14'-oxaspiro[oxolane-2,13'-tetracyclo[9.3.2.0¹,¹⁰.0²,⁷]hexadecane]-2',4',6'-triene-3,8'-diol)

Structure for NP0279745 (5'-methoxy-4,5,5,6',10',12'-hexamethyl-14'-oxaspiro[oxolane-2,13'-tetracyclo[9.3.2.0¹,¹⁰.0²,⁷]hexadecane]-2',4',6'-triene-3,8'-diol)

3D Structure for NP0279745 (5'-methoxy-4,5,5,6',10',12'-hexamethyl-14'-oxaspiro[oxolane-2,13'-tetracyclo[9.3.2.0¹,¹⁰.0²,⁷]hexadecane]-2',4',6'-triene-3,8'-diol)