NP-MRD: Showing NP-Card for (5as,7as,9r,11ar,11br,12s)-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 (NP0320605)

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Record Information

Version

2.0

Created at

2022-09-11 22:20:52 UTC

Updated at

2022-09-11 22:20:52 UTC

NP-MRD ID

NP0320605

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(5as,7as,9r,11ar,11br,12s)-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

(5AS,7aS,9R,11aR,11bR,12S)-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. (5as,7as,9r,11ar,11br,12s)-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. Based on a literature review very few articles have been published on (5aS,7aS,9R,11aR,11bR,12S)-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.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309122200202D          

 34 38  0  0  1  0            999 V2000
    0.6019   -1.9066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    4.1124   -2.6861    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

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M  END


  Mrv1652309122200202D          

 34 38  0  0  1  0            999 V2000
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 28 29  1  0  0  0  0
 29 30  1  1  0  0  0
 31 29  1  1  0  0  0
 13 31  1  0  0  0  0
  8 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>
NP0320605

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)O[C@@H]1CC[C@]2(C)[C@H](CC[C@]3(C)OC4=C([C@@H](O)[C@@H]23)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/t19-,20-,22-,23+,26-,27+/m1/s1

> <INCHI_KEY>
CRIDZJKECHTODK-YHWNCLHNSA-N

> <FORMULA>
C27H33NO6

> <MOLECULAR_WEIGHT>
467.562

> <EXACT_MASS>
467.230787787

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
67

> <JCHEM_AVERAGE_POLARIZABILITY>
51.382221311549564

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(5aS,7aS,9R,11aR,11bR,12S)-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

> <JCHEM_LOGP>
2.3797673489999984

> <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>
94.95

> <JCHEM_REFRACTIVITY>
126.42259999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(5aS,7aS,9R,11aR,11bR,12S)-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                                 12-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-SEP-22         0                                  
HETATM    1  C   UNK     0       1.123  -3.559   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.636  -3.268   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       3.140  -1.813   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       3.644  -4.432   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       5.156  -4.141   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.164  -5.305   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.677  -5.014   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.181  -3.559   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.189  -4.723   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.172  -2.395   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.677  -0.940   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       9.189  -0.649   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      10.197  -1.813   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      10.701  -0.358   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      11.709  -1.522   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      12.717  -2.686   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      14.230  -2.395   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      15.238  -3.559   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      16.750  -3.268   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      17.254  -1.813   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      18.766  -1.522   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      19.775  -2.686   0.000  0.00  0.00           C+0
HETATM   23  N   UNK     0      19.270  -4.141   0.000  0.00  0.00           N+0
HETATM   24  C   UNK     0      17.758  -4.432   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      14.734  -5.014   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      13.221  -5.305   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      12.717  -6.760   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      12.213  -4.141   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      10.701  -4.432   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      10.197  -5.887   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       9.693  -3.268   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       5.660  -2.686   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       5.317  -1.185   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       4.224  -2.131   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   31                                             
CONECT    9    8                                                            
CONECT   10    8   11   32                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   15   31                                             
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15   17   28                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   25                                                  
CONECT   19   18   20   24                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   19                                                       
CONECT   25   18   26                                                       
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   16   29                                                  
CONECT   29   28   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   13    8                                                  
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
(5AS,7as,9R,11ar,11BR,12S)-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

(5aS,7aS,9R,11aR,11bR,12S)-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

(5aS,7aS,9R,11aR,11bR,12S)-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)O[C@@H]1CC[C@]2(C)[C@H](CC[C@]3(C)OC4=C([C@@H](O)[C@@H]23)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/t19-,20-,22-,23+,26-,27+/m1/s1

InChI Key

CRIDZJKECHTODK-YHWNCLHNSA-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
Pyranone
Alkyl aryl ether
Pyridine
Pyran
Heteroaromatic compound
Vinylogous ester
Secondary alcohol
Lactone
Carboxylic acid ester
Oxacycle
Azacycle
Monocarboxylic acid or derivatives
Ether
Carboxylic acid derivative
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen 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	2.38	ChemAxon
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	51.38 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

163035629

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (5as,7as,9r,11ar,11br,12s)-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 (NP0320605)

MOL for NP0320605 ((5as,7as,9r,11ar,11br,12s)-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 NP0320605 ((5as,7as,9r,11ar,11br,12s)-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 NP0320605 ((5as,7as,9r,11ar,11br,12s)-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 NP0320605 ((5as,7as,9r,11ar,11br,12s)-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 NP0320605 ((5as,7as,9r,11ar,11br,12s)-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 NP0320605 ((5as,7as,9r,11ar,11br,12s)-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 NP0320605 ((5as,7as,9r,11ar,11br,12s)-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 NP0320605 ((5as,7as,9r,11ar,11br,12s)-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 NP0320605 ((5as,7as,9r,11ar,11br,12s)-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 NP0320605 ((5as,7as,9r,11ar,11br,12s)-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)