NP-MRD: Showing NP-Card for 8-[(acetyloxy)methyl]-5a,8,11a-trimethyl-1-oxo-3-(pyridin-3-yl)-6,7,7a,9,10,11,11b,12-octahydro-2,5-dioxatetraphen-9-yl propanoate (NP0273520)

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Record Information

Version

2.0

Created at

2022-09-08 20:35:48 UTC

Updated at

2022-09-08 20:35:48 UTC

NP-MRD ID

NP0273520

Secondary Accession Numbers

None

Natural Product Identification

Common Name

8-[(acetyloxy)methyl]-5a,8,11a-trimethyl-1-oxo-3-(pyridin-3-yl)-6,7,7a,9,10,11,11b,12-octahydro-2,5-dioxatetraphen-9-yl propanoate

Description

8-[(Acetyloxy)methyl]-5a,8,11a-trimethyl-1-oxo-3-(pyridin-3-yl)-1,5a,6,7,7a,8,9,10,11,11a,11b,12-dodecahydro-2,5-dioxatetraphen-9-yl propanoate belongs to the class of organic compounds known as steroids and steroid derivatives. Steroids and steroid derivatives are compounds based on the cyclopenta[a]phenanthrene carbon skeleton, partially or completely hydrogenated; there are usually methyl groups at C-10 and C-13, and often an alkyl group at C-17. By extension, one or more bond scissions, ring expansions and/or ring contractions of the skeleton may have occurred. 8-[(acetyloxy)methyl]-5a,8,11a-trimethyl-1-oxo-3-(pyridin-3-yl)-6,7,7a,9,10,11,11b,12-octahydro-2,5-dioxatetraphen-9-yl propanoate is found in Aspergillus fumigatus. Based on a literature review very few articles have been published on 8-[(acetyloxy)methyl]-5a,8,11a-trimethyl-1-oxo-3-(pyridin-3-yl)-1,5a,6,7,7a,8,9,10,11,11a,11b,12-dodecahydro-2,5-dioxatetraphen-9-yl propanoate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309082222352D          

 38 42  0  0  0  0            999 V2000
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M  END

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M  END


  Mrv1652309082222352D          

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    1.3502   -1.5850    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5401   -1.7409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2700   -2.5204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5401   -2.6764    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7242   -1.8722    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3097   -2.3793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9519   -2.8973    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7215   -2.6002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3636   -3.1182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8490   -1.7851    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 17 22  1  0  0  0  0
 16 23  1  0  0  0  0
 23 24  1  0  0  0  0
 13 24  1  0  0  0  0
 24 25  2  0  0  0  0
 14 26  1  0  0  0  0
 26 27  1  0  0  0  0
 11 27  1  0  0  0  0
 27 28  1  0  0  0  0
 27 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
  9 31  1  0  0  0  0
 31 32  1  0  0  0  0
  6 32  1  0  0  0  0
 32 33  1  0  0  0  0
 32 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 36 37  1  0  0  0  0
 36 38  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0273520

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCC(=O)OC1CCC2(C)C(CCC3(C)OC4=C(CC23)C(=O)OC(=C4)C2=CC=CN=C2)C1(C)COC(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C30H37NO7/c1-6-26(33)37-25-10-11-28(3)23(29(25,4)17-35-18(2)32)9-12-30(5)24(28)14-20-22(38-30)15-21(36-27(20)34)19-8-7-13-31-16-19/h7-8,13,15-16,23-25H,6,9-12,14,17H2,1-5H3

> <INCHI_KEY>
KOPSWANPSRYSOD-UHFFFAOYSA-N

> <FORMULA>
C30H37NO7

> <MOLECULAR_WEIGHT>
523.626

> <EXACT_MASS>
523.257002535

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
75

> <JCHEM_AVERAGE_POLARIZABILITY>
57.94850963500272

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
8-[(acetyloxy)methyl]-5a,8,11a-trimethyl-1-oxo-3-(pyridin-3-yl)-1,5a,6,7,7a,8,9,10,11,11a,11b,12-dodecahydro-2,5-dioxatetraphen-9-yl propanoate

> <JCHEM_LOGP>
3.429911789666665

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
4.206464980867094

> <JCHEM_POLAR_SURFACE_AREA>
101.02000000000001

> <JCHEM_REFRACTIVITY>
140.559

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
8-[(acetyloxy)methyl]-5a,8,11a-trimethyl-1-oxo-3-(pyridin-3-yl)-6,7,7a,9,10,11,11b,12-octahydro-2,5-dioxatetraphen-9-yl propanoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 08-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   08-SEP-22         0                                  
HETATM    1  C   UNK     0      -3.024 -10.817   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.520  -9.361   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -3.529  -8.197   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      -5.041  -8.488   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0      -3.024  -6.742   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      -1.512  -6.451   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.504  -7.615   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.008  -7.324   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.512  -5.869   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.520  -7.033   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.024  -5.578   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.033  -6.742   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.545  -6.451   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.049  -4.996   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.561  -4.705   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.569  -5.869   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      10.082  -5.578   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      10.586  -4.123   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      12.098  -3.832   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      13.106  -4.996   0.000  0.00  0.00           C+0
HETATM   21  N   UNK     0      12.602  -6.451   0.000  0.00  0.00           N+0
HETATM   22  C   UNK     0      11.090  -6.742   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       8.065  -7.324   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       6.553  -7.615   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       6.049  -9.070   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0       5.041  -3.832   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       3.529  -4.123   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       4.033  -2.668   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       2.520  -2.959   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       1.008  -3.250   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       0.504  -4.705   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -1.008  -4.996   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -1.352  -3.495   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      -2.445  -4.441   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0      -3.643  -5.408   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0      -5.080  -4.854   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      -6.279  -5.821   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0      -5.318  -3.332   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7   32                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   11   31                                             
CONECT   10    9                                                            
CONECT   11    9   12   27                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   24                                                  
CONECT   14   13   15   26                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   23                                                  
CONECT   17   16   18   22                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   17                                                       
CONECT   23   16   24                                                       
CONECT   24   23   13   25                                                  
CONECT   25   24                                                            
CONECT   26   14   27                                                       
CONECT   27   26   11   28   29                                             
CONECT   28   27                                                            
CONECT   29   27   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30    9   32                                                  
CONECT   32   31    6   33   34                                             
CONECT   33   32                                                            
CONECT   34   32   35                                                       
CONECT   35   34   36                                                       
CONECT   36   35   37   38                                                  
CONECT   37   36                                                            
CONECT   38   36                                                            
MASTER        0    0    0    0    0    0    0    0   38    0   84    0
END

View in JSmol

Synonyms

Value	Source
8-[(Acetyloxy)methyl]-5a,8,11a-trimethyl-1-oxo-3-(pyridin-3-yl)-1,5a,6,7,7a,8,9,10,11,11a,11b,12-dodecahydro-2,5-dioxatetraphen-9-yl propanoic acid	Generator

Chemical Formula

C₃₀H₃₇NO₇

Average Mass

523.6260 Da

Monoisotopic Mass

523.25700 Da

IUPAC Name

8-[(acetyloxy)methyl]-5a,8,11a-trimethyl-1-oxo-3-(pyridin-3-yl)-1,5a,6,7,7a,8,9,10,11,11a,11b,12-dodecahydro-2,5-dioxatetraphen-9-yl propanoate

Traditional Name

8-[(acetyloxy)methyl]-5a,8,11a-trimethyl-1-oxo-3-(pyridin-3-yl)-6,7,7a,9,10,11,11b,12-octahydro-2,5-dioxatetraphen-9-yl propanoate

CAS Registry Number

Not Available

SMILES

CCC(=O)OC1CCC2(C)C(CCC3(C)OC4=C(CC23)C(=O)OC(=C4)C2=CC=CN=C2)C1(C)COC(C)=O

InChI Identifier

InChI=1S/C30H37NO7/c1-6-26(33)37-25-10-11-28(3)23(29(25,4)17-35-18(2)32)9-12-30(5)24(28)14-20-22(38-30)15-21(36-27(20)34)19-8-7-13-31-16-19/h7-8,13,15-16,23-25H,6,9-12,14,17H2,1-5H3

InChI Key

KOPSWANPSRYSOD-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 steroids and steroid derivatives. Steroids and steroid derivatives are compounds based on the cyclopenta[a]phenanthrene carbon skeleton, partially or completely hydrogenated; there are usually methyl groups at C-10 and C-13, and often an alkyl group at C-17. By extension, one or more bond scissions, ring expansions and/or ring contractions of the skeleton may have occurred.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Not Available

Direct Parent

Steroids and steroid derivatives

Alternative Parents

Substituents

Steroid
Naphthopyran
Naphthalene
Alkyl aryl ether
Pyranone
Dicarboxylic acid or derivatives
Pyran
Pyridine
Heteroaromatic compound
Vinylogous ester
Carboxylic acid ester
Lactone
Carboxylic acid derivative
Ether
Oxacycle
Azacycle
Organoheterocyclic compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Carbonyl group
Organonitrogen compound
Organooxygen compound
Organic nitrogen compound
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	3.43	ChemAxon
pKa (Strongest Basic)	4.21	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	101.02 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	140.56 m³·mol⁻¹	ChemAxon
Polarizability	57.95 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	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

85227823

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 8-[(acetyloxy)methyl]-5a,8,11a-trimethyl-1-oxo-3-(pyridin-3-yl)-6,7,7a,9,10,11,11b,12-octahydro-2,5-dioxatetraphen-9-yl propanoate (NP0273520)

MOL for NP0273520 (8-[(acetyloxy)methyl]-5a,8,11a-trimethyl-1-oxo-3-(pyridin-3-yl)-6,7,7a,9,10,11,11b,12-octahydro-2,5-dioxatetraphen-9-yl propanoate)

3D MOL for NP0273520 (8-[(acetyloxy)methyl]-5a,8,11a-trimethyl-1-oxo-3-(pyridin-3-yl)-6,7,7a,9,10,11,11b,12-octahydro-2,5-dioxatetraphen-9-yl propanoate)

3D SDF for NP0273520 (8-[(acetyloxy)methyl]-5a,8,11a-trimethyl-1-oxo-3-(pyridin-3-yl)-6,7,7a,9,10,11,11b,12-octahydro-2,5-dioxatetraphen-9-yl propanoate)

3D-SDF for NP0273520 (8-[(acetyloxy)methyl]-5a,8,11a-trimethyl-1-oxo-3-(pyridin-3-yl)-6,7,7a,9,10,11,11b,12-octahydro-2,5-dioxatetraphen-9-yl propanoate)

PDB for NP0273520 (8-[(acetyloxy)methyl]-5a,8,11a-trimethyl-1-oxo-3-(pyridin-3-yl)-6,7,7a,9,10,11,11b,12-octahydro-2,5-dioxatetraphen-9-yl propanoate)

3D PDB for NP0273520 (8-[(acetyloxy)methyl]-5a,8,11a-trimethyl-1-oxo-3-(pyridin-3-yl)-6,7,7a,9,10,11,11b,12-octahydro-2,5-dioxatetraphen-9-yl propanoate)

SMILES for NP0273520 (8-[(acetyloxy)methyl]-5a,8,11a-trimethyl-1-oxo-3-(pyridin-3-yl)-6,7,7a,9,10,11,11b,12-octahydro-2,5-dioxatetraphen-9-yl propanoate)

INCHI for NP0273520 (8-[(acetyloxy)methyl]-5a,8,11a-trimethyl-1-oxo-3-(pyridin-3-yl)-6,7,7a,9,10,11,11b,12-octahydro-2,5-dioxatetraphen-9-yl propanoate)

Structure for NP0273520 (8-[(acetyloxy)methyl]-5a,8,11a-trimethyl-1-oxo-3-(pyridin-3-yl)-6,7,7a,9,10,11,11b,12-octahydro-2,5-dioxatetraphen-9-yl propanoate)

3D Structure for NP0273520 (8-[(acetyloxy)methyl]-5a,8,11a-trimethyl-1-oxo-3-(pyridin-3-yl)-6,7,7a,9,10,11,11b,12-octahydro-2,5-dioxatetraphen-9-yl propanoate)