NP-MRD: Showing NP-Card for 2-acetyl-12-(acetyloxy)-7-ethyl-4b,7,10a,12a-tetramethyl-3-oxo-6,6a,8,9,10,10b,11,12-octahydro-5h-chrysene-1-carboxylic acid (NP0168708)

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Record Information

Version

1.0

Created at

2022-09-03 04:33:41 UTC

Updated at

2022-09-03 04:33:41 UTC

NP-MRD ID

NP0168708

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2-acetyl-12-(acetyloxy)-7-ethyl-4b,7,10a,12a-tetramethyl-3-oxo-6,6a,8,9,10,10b,11,12-octahydro-5h-chrysene-1-carboxylic acid

Description

2-Acetyl-12-(acetyloxy)-7-ethyl-4b,7,10a,12a-tetramethyl-3-oxo-3,4b,5,6,6a,7,8,9,10,10a,10b,11,12,12a-tetradecahydrochrysene-1-carboxylic acid belongs to the class of organic compounds known as scalarane sesterterpenoids. These are sesterterpenoids with a structure based on the scalarane backbone. Scalarane is a tetracyclic compound, which is similar the homoandrostane with five methyl groups at the 4-, 4-, 8-, 17-, 17a-positions. 2-acetyl-12-(acetyloxy)-7-ethyl-4b,7,10a,12a-tetramethyl-3-oxo-6,6a,8,9,10,10b,11,12-octahydro-5h-chrysene-1-carboxylic acid is found in Carteriospongia foliascens. 2-Acetyl-12-(acetyloxy)-7-ethyl-4b,7,10a,12a-tetramethyl-3-oxo-3,4b,5,6,6a,7,8,9,10,10a,10b,11,12,12a-tetradecahydrochrysene-1-carboxylic acid is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004251512332D          

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M  END

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  Mrv1533004251512332D          

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  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
  8 10  1  0  0  0  0
  3 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
  8 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
 17 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 26 28  1  0  0  0  0
 25 29  1  0  0  0  0
 29 30  2  0  0  0  0
 29 31  1  0  0  0  0
 31 32  2  0  0  0  0
 13 32  1  0  0  0  0
 22 32  1  0  0  0  0
 24 33  1  0  0  0  0
 33 34  2  0  0  0  0
 33 35  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0168708

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCC1(C)CCCC2(C)C1CCC1(C)C2CC(OC(C)=O)C2(C)C1=CC(=O)C(C(C)=O)=C2C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C29H40O6/c1-8-26(4)11-9-12-27(5)19(26)10-13-28(6)20(27)15-22(35-17(3)31)29(7)21(28)14-18(32)23(16(2)30)24(29)25(33)34/h14,19-20,22H,8-13,15H2,1-7H3,(H,33,34)

> <INCHI_KEY>
FUIYHMIILZPRHG-UHFFFAOYSA-N

> <FORMULA>
C29H40O6

> <MOLECULAR_WEIGHT>
484.633

> <EXACT_MASS>
484.282489008

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
75

> <JCHEM_AVERAGE_POLARIZABILITY>
53.69479113327233

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-acetyl-12-(acetyloxy)-7-ethyl-4b,7,10a,12a-tetramethyl-3-oxo-3,4b,5,6,6a,7,8,9,10,10a,10b,11,12,12a-tetradecahydrochrysene-1-carboxylic acid

> <ALOGPS_LOGP>
4.97

> <JCHEM_LOGP>
4.932545345666666

> <ALOGPS_LOGS>
-6.33

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
18.316566414062763

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.4190173304717333

> <JCHEM_PKA_STRONGEST_BASIC>
-7.004257974519532

> <JCHEM_POLAR_SURFACE_AREA>
97.74000000000001

> <JCHEM_REFRACTIVITY>
133.0

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.26e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-acetyl-12-(acetyloxy)-7-ethyl-4b,7,10a,12a-tetramethyl-3-oxo-6,6a,8,9,10,10b,11,12-octahydro-5H-chrysene-1-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 25-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   25-APR-15         0                                  
HETATM    1  C   UNK     0      10.192   4.556   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      10.216   3.016   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.895   2.225   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.346   3.664   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       9.903   1.061   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.399  -0.394   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.887  -0.685   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.879   0.479   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.375  -0.976   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.383   1.934   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.375   3.098   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.862   2.807   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.358   1.352   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.350   2.516   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.366   0.188   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.862  -1.267   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.350  -1.558   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       2.846  -3.013   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       3.854  -4.178   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       5.366  -3.887   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       3.350  -5.633   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       2.342  -0.394   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       1.838  -1.849   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       0.830  -0.685   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -0.179   0.479   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -1.691   0.188   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      -2.195  -1.267   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      -2.699   1.352   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       0.326   1.934   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      -0.683   3.098   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       1.838   2.225   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       2.846   1.061   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       0.326  -2.140   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      -1.187  -2.431   0.000  0.00  0.00           O+0
HETATM   35  O   UNK     0       1.334  -3.304   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5   10                                             
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   10   15                                             
CONECT    9    8                                                            
CONECT   10    8    3   11                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   15   32                                             
CONECT   14   13                                                            
CONECT   15   13    8   16                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   22                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19                                                            
CONECT   22   17   23   24   32                                             
CONECT   23   22                                                            
CONECT   24   22   25   33                                                  
CONECT   25   24   26   29                                                  
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26                                                            
CONECT   29   25   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   32                                                       
CONECT   32   31   13   22                                                  
CONECT   33   24   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33                                                            
MASTER        0    0    0    0    0    0    0    0   35    0   76    0
END

View in JSmol

Synonyms

Value	Source
2-Acetyl-12-(acetyloxy)-7-ethyl-4b,7,10a,12a-tetramethyl-3-oxo-3,4b,5,6,6a,7,8,9,10,10a,10b,11,12,12a-tetradecahydrochrysene-1-carboxylate	Generator

Chemical Formula

C₂₉H₄₀O₆

Average Mass

484.6330 Da

Monoisotopic Mass

484.28249 Da

IUPAC Name

2-acetyl-12-(acetyloxy)-7-ethyl-4b,7,10a,12a-tetramethyl-3-oxo-3,4b,5,6,6a,7,8,9,10,10a,10b,11,12,12a-tetradecahydrochrysene-1-carboxylic acid

Traditional Name

2-acetyl-12-(acetyloxy)-7-ethyl-4b,7,10a,12a-tetramethyl-3-oxo-6,6a,8,9,10,10b,11,12-octahydro-5H-chrysene-1-carboxylic acid

CAS Registry Number

Not Available

SMILES

CCC1(C)CCCC2(C)C1CCC1(C)C2CC(OC(C)=O)C2(C)C1=CC(=O)C(C(C)=O)=C2C(O)=O

InChI Identifier

InChI=1S/C29H40O6/c1-8-26(4)11-9-12-27(5)19(26)10-13-28(6)20(27)15-22(35-17(3)31)29(7)21(28)14-18(32)23(16(2)30)24(29)25(33)34/h14,19-20,22H,8-13,15H2,1-7H3,(H,33,34)

InChI Key

FUIYHMIILZPRHG-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
Phyllospongia foliascens	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as scalarane sesterterpenoids. These are sesterterpenoids with a structure based on the scalarane backbone. Scalarane is a tetracyclic compound, which is similar the homoandrostane with five methyl groups at the 4-, 4-, 8-, 17-, 17a-positions.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesterterpenoids

Direct Parent

Scalarane sesterterpenoids

Alternative Parents

Substituents

Scalarane sesterterpenoid
15-hydroxysteroid
Oxosteroid
12-oxosteroid
17-oxosteroid
Hydroxysteroid
Steroid
Dicarboxylic acid or derivatives
Carboxylic acid ester
Cyclic ketone
Ketone
Carboxylic acid derivative
Carboxylic acid
Organic oxide
Carbonyl group
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic 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	4.97	ALOGPS
logP	4.93	ChemAxon
logS	-6.3	ALOGPS
pKa (Strongest Acidic)	2.42	ChemAxon
pKa (Strongest Basic)	-7	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	97.74 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	133 m³·mol⁻¹	ChemAxon
Polarizability	53.69 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	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

74051537

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 2-acetyl-12-(acetyloxy)-7-ethyl-4b,7,10a,12a-tetramethyl-3-oxo-6,6a,8,9,10,10b,11,12-octahydro-5h-chrysene-1-carboxylic acid (NP0168708)

MOL for NP0168708 (2-acetyl-12-(acetyloxy)-7-ethyl-4b,7,10a,12a-tetramethyl-3-oxo-6,6a,8,9,10,10b,11,12-octahydro-5h-chrysene-1-carboxylic acid)

3D MOL for NP0168708 (2-acetyl-12-(acetyloxy)-7-ethyl-4b,7,10a,12a-tetramethyl-3-oxo-6,6a,8,9,10,10b,11,12-octahydro-5h-chrysene-1-carboxylic acid)

3D SDF for NP0168708 (2-acetyl-12-(acetyloxy)-7-ethyl-4b,7,10a,12a-tetramethyl-3-oxo-6,6a,8,9,10,10b,11,12-octahydro-5h-chrysene-1-carboxylic acid)

3D-SDF for NP0168708 (2-acetyl-12-(acetyloxy)-7-ethyl-4b,7,10a,12a-tetramethyl-3-oxo-6,6a,8,9,10,10b,11,12-octahydro-5h-chrysene-1-carboxylic acid)

PDB for NP0168708 (2-acetyl-12-(acetyloxy)-7-ethyl-4b,7,10a,12a-tetramethyl-3-oxo-6,6a,8,9,10,10b,11,12-octahydro-5h-chrysene-1-carboxylic acid)

3D PDB for NP0168708 (2-acetyl-12-(acetyloxy)-7-ethyl-4b,7,10a,12a-tetramethyl-3-oxo-6,6a,8,9,10,10b,11,12-octahydro-5h-chrysene-1-carboxylic acid)

SMILES for NP0168708 (2-acetyl-12-(acetyloxy)-7-ethyl-4b,7,10a,12a-tetramethyl-3-oxo-6,6a,8,9,10,10b,11,12-octahydro-5h-chrysene-1-carboxylic acid)

INCHI for NP0168708 (2-acetyl-12-(acetyloxy)-7-ethyl-4b,7,10a,12a-tetramethyl-3-oxo-6,6a,8,9,10,10b,11,12-octahydro-5h-chrysene-1-carboxylic acid)

Structure for NP0168708 (2-acetyl-12-(acetyloxy)-7-ethyl-4b,7,10a,12a-tetramethyl-3-oxo-6,6a,8,9,10,10b,11,12-octahydro-5h-chrysene-1-carboxylic acid)

3D Structure for NP0168708 (2-acetyl-12-(acetyloxy)-7-ethyl-4b,7,10a,12a-tetramethyl-3-oxo-6,6a,8,9,10,10b,11,12-octahydro-5h-chrysene-1-carboxylic acid)