NP-MRD: Showing NP-Card for 12-hydroxy-5a,8,8,11a-tetramethyl-1-oxo-3-(pyridin-3-yl)-6,7,7a,9,10,11,11b,12-octahydro-2,5-dioxatetraphen-9-yl acetate (NP0308465)

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Record Information

Version

2.0

Created at

2022-09-11 02:15:23 UTC

Updated at

2022-09-11 02:15:24 UTC

NP-MRD ID

NP0308465

Secondary Accession Numbers

None

Natural Product Identification

Common Name

12-hydroxy-5a,8,8,11a-tetramethyl-1-oxo-3-(pyridin-3-yl)-6,7,7a,9,10,11,11b,12-octahydro-2,5-dioxatetraphen-9-yl acetate

Description

12-Hydroxy-5a,8,8,11a-tetramethyl-1-oxo-3-(pyridin-3-yl)-1,5a,6,7,7a,8,9,10,11,11a,11b,12-dodecahydro-2,5-dioxatetraphen-9-yl acetate 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. 12-hydroxy-5a,8,8,11a-tetramethyl-1-oxo-3-(pyridin-3-yl)-6,7,7a,9,10,11,11b,12-octahydro-2,5-dioxatetraphen-9-yl acetate is found in Aspergillus fumigatus. 12-Hydroxy-5a,8,8,11a-tetramethyl-1-oxo-3-(pyridin-3-yl)-1,5a,6,7,7a,8,9,10,11,11a,11b,12-dodecahydro-2,5-dioxatetraphen-9-yl acetate is a strong basic compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004191518252D          

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M  END

     RDKit          3D

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M  END


  Mrv1533004191518252D          

 34 38  0  0  0  0            999 V2000
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 26 31  1  0  0  0  0
 10 32  1  0  0  0  0
  5 32  1  0  0  0  0
 32 33  1  0  0  0  0
 32 34  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0308465

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)OC1CCC2(C)C(CCC3(C)OC4=C(C(O)C23)C(=O)OC(=C4)C2=CC=CN=C2)C1(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C27H33NO6/c1-15(29)32-20-9-10-26(4)19(25(20,2)3)8-11-27(5)23(26)22(30)21-18(34-27)13-17(33-24(21)31)16-7-6-12-28-14-16/h6-7,12-14,19-20,22-23,30H,8-11H2,1-5H3

> <INCHI_KEY>
CRIDZJKECHTODK-UHFFFAOYSA-N

> <FORMULA>
C27H33NO6

> <MOLECULAR_WEIGHT>
467.562

> <EXACT_MASS>
467.230787787

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
67

> <JCHEM_AVERAGE_POLARIZABILITY>
51.26777990843112

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
12-hydroxy-5a,8,8,11a-tetramethyl-1-oxo-3-(pyridin-3-yl)-1,5a,6,7,7a,8,9,10,11,11a,11b,12-dodecahydro-2,5-dioxatetraphen-9-yl acetate

> <ALOGPS_LOGP>
4.13

> <JCHEM_LOGP>
2.3797673489999984

> <ALOGPS_LOGS>
-4.80

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.84399314057027

> <JCHEM_PKA_STRONGEST_BASIC>
4.206339572640568

> <JCHEM_POLAR_SURFACE_AREA>
94.95000000000002

> <JCHEM_REFRACTIVITY>
126.42259999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.35e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
12-hydroxy-5a,8,8,11a-tetramethyl-1-oxo-3-(pyridin-3-yl)-6,7,7a,9,10,11,11b,12-octahydro-2,5-dioxatetraphen-9-yl acetate

> <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      -9.546  -4.141   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -8.034  -4.432   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -7.530  -5.887   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      -7.026  -3.268   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      -5.513  -3.559   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -4.505  -2.395   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.993  -2.686   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.489  -4.141   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.481  -2.977   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -3.497  -5.305   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -2.993  -6.760   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.481  -7.051   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.472  -5.887   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.032  -7.342   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       1.040  -6.178   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       2.048  -5.014   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.544  -3.559   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.032  -3.268   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -0.472  -1.813   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      -0.977  -4.432   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.552  -2.395   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       2.048  -0.940   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       4.064  -2.686   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       4.568  -4.141   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       3.560  -5.305   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       6.081  -4.432   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       7.089  -3.268   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       8.601  -3.559   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       9.105  -5.014   0.000  0.00  0.00           C+0
HETATM   30  N   UNK     0       8.097  -6.178   0.000  0.00  0.00           N+0
HETATM   31  C   UNK     0       6.585  -5.887   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -5.009  -5.014   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -5.353  -6.515   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      -6.446  -5.569   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6   32                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   10   20                                             
CONECT    9    8                                                            
CONECT   10    8   11   32                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   15   20                                             
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15   17   25                                                  
CONECT   17   16   18   21                                                  
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18    8   13                                                  
CONECT   21   17   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24                                                       
CONECT   24   23   25   26                                                  
CONECT   25   24   16                                                       
CONECT   26   24   27   31                                                  
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   26                                                       
CONECT   32   10    5   33   34                                             
CONECT   33   32                                                            
CONECT   34   32                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   76    0
END

View in JSmol

Synonyms

Value	Source
12-Hydroxy-5a,8,8,11a-tetramethyl-1-oxo-3-(pyridin-3-yl)-1,5a,6,7,7a,8,9,10,11,11a,11b,12-dodecahydro-2,5-dioxatetraphen-9-yl acetic acid	Generator

Chemical Formula

C₂₇H₃₃NO₆

Average Mass

467.5620 Da

Monoisotopic Mass

467.23079 Da

IUPAC Name

12-hydroxy-5a,8,8,11a-tetramethyl-1-oxo-3-(pyridin-3-yl)-1,5a,6,7,7a,8,9,10,11,11a,11b,12-dodecahydro-2,5-dioxatetraphen-9-yl acetate

Traditional Name

12-hydroxy-5a,8,8,11a-tetramethyl-1-oxo-3-(pyridin-3-yl)-6,7,7a,9,10,11,11b,12-octahydro-2,5-dioxatetraphen-9-yl acetate

CAS Registry Number

Not Available

SMILES

CC(=O)OC1CCC2(C)C(CCC3(C)OC4=C(C(O)C23)C(=O)OC(=C4)C2=CC=CN=C2)C1(C)C

InChI Identifier

InChI=1S/C27H33NO6/c1-15(29)32-20-9-10-26(4)19(25(20,2)3)8-11-27(5)23(26)22(30)21-18(34-27)13-17(33-24(21)31)16-7-6-12-28-14-16/h6-7,12-14,19-20,22-23,30H,8-11H2,1-5H3

InChI Key

CRIDZJKECHTODK-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
Aspergillus fumigatus	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
Alkyl aryl ether
Pyranone
Pyran
Pyridine
Heteroaromatic compound
Vinylogous ester
Carboxylic acid ester
Lactone
Secondary alcohol
Carboxylic acid derivative
Ether
Monocarboxylic acid or derivatives
Oxacycle
Azacycle
Organic oxide
Organopnictogen compound
Organic nitrogen compound
Organic oxygen compound
Hydrocarbon derivative
Organonitrogen compound
Organooxygen compound
Carbonyl group
Alcohol
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	4.13	ALOGPS
logP	2.38	ChemAxon
logS	-4.8	ALOGPS
pKa (Strongest Acidic)	13.84	ChemAxon
pKa (Strongest Basic)	4.21	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	94.95 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	126.42 m³·mol⁻¹	ChemAxon
Polarizability	51.27 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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 12-hydroxy-5a,8,8,11a-tetramethyl-1-oxo-3-(pyridin-3-yl)-6,7,7a,9,10,11,11b,12-octahydro-2,5-dioxatetraphen-9-yl acetate (NP0308465)

MOL for NP0308465 (12-hydroxy-5a,8,8,11a-tetramethyl-1-oxo-3-(pyridin-3-yl)-6,7,7a,9,10,11,11b,12-octahydro-2,5-dioxatetraphen-9-yl acetate)

3D MOL for NP0308465 (12-hydroxy-5a,8,8,11a-tetramethyl-1-oxo-3-(pyridin-3-yl)-6,7,7a,9,10,11,11b,12-octahydro-2,5-dioxatetraphen-9-yl acetate)

3D SDF for NP0308465 (12-hydroxy-5a,8,8,11a-tetramethyl-1-oxo-3-(pyridin-3-yl)-6,7,7a,9,10,11,11b,12-octahydro-2,5-dioxatetraphen-9-yl acetate)

3D-SDF for NP0308465 (12-hydroxy-5a,8,8,11a-tetramethyl-1-oxo-3-(pyridin-3-yl)-6,7,7a,9,10,11,11b,12-octahydro-2,5-dioxatetraphen-9-yl acetate)

PDB for NP0308465 (12-hydroxy-5a,8,8,11a-tetramethyl-1-oxo-3-(pyridin-3-yl)-6,7,7a,9,10,11,11b,12-octahydro-2,5-dioxatetraphen-9-yl acetate)

3D PDB for NP0308465 (12-hydroxy-5a,8,8,11a-tetramethyl-1-oxo-3-(pyridin-3-yl)-6,7,7a,9,10,11,11b,12-octahydro-2,5-dioxatetraphen-9-yl acetate)

SMILES for NP0308465 (12-hydroxy-5a,8,8,11a-tetramethyl-1-oxo-3-(pyridin-3-yl)-6,7,7a,9,10,11,11b,12-octahydro-2,5-dioxatetraphen-9-yl acetate)

INCHI for NP0308465 (12-hydroxy-5a,8,8,11a-tetramethyl-1-oxo-3-(pyridin-3-yl)-6,7,7a,9,10,11,11b,12-octahydro-2,5-dioxatetraphen-9-yl acetate)

Structure for NP0308465 (12-hydroxy-5a,8,8,11a-tetramethyl-1-oxo-3-(pyridin-3-yl)-6,7,7a,9,10,11,11b,12-octahydro-2,5-dioxatetraphen-9-yl acetate)

3D Structure for NP0308465 (12-hydroxy-5a,8,8,11a-tetramethyl-1-oxo-3-(pyridin-3-yl)-6,7,7a,9,10,11,11b,12-octahydro-2,5-dioxatetraphen-9-yl acetate)