NP-MRD: Showing NP-Card for 8-acetyl-2',4a,6a,10b-tetramethyl-9-oxo-3,4,4b,5,6,10,10a,11,12,12a-decahydro-2h-spiro[chrysene-1,1'-cyclopropan]-6-yl 3-hydroxybutanoate (NP0179015)

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Record Information

Version

1.0

Created at

2022-09-03 17:07:44 UTC

Updated at

2022-09-03 17:07:44 UTC

NP-MRD ID

NP0179015

Secondary Accession Numbers

None

Natural Product Identification

Common Name

8-acetyl-2',4a,6a,10b-tetramethyl-9-oxo-3,4,4b,5,6,10,10a,11,12,12a-decahydro-2h-spiro[chrysene-1,1'-cyclopropan]-6-yl 3-hydroxybutanoate

Description

8-Acetyl-3',4a,6a,10b-tetramethyl-9-oxo-3,4,4a,4b,5,6,6a,9,10,10a,10b,11,12,12a-tetradecahydro-2H-spiro[chrysene-1,1'-cyclopropane]-6-yl 3-hydroxybutanoate belongs to the class of organic compounds known as beta hydroxy acids and derivatives. Beta hydroxy acids and derivatives are compounds containing a carboxylic acid substituted with a hydroxyl group on the C3 carbon atom. 8-acetyl-2',4a,6a,10b-tetramethyl-9-oxo-3,4,4b,5,6,10,10a,11,12,12a-decahydro-2h-spiro[chrysene-1,1'-cyclopropan]-6-yl 3-hydroxybutanoate is found in Strepsichordaia aliena. 8-Acetyl-3',4a,6a,10b-tetramethyl-9-oxo-3,4,4a,4b,5,6,6a,9,10,10a,10b,11,12,12a-tetradecahydro-2H-spiro[chrysene-1,1'-cyclopropane]-6-yl 3-hydroxybutanoate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004231521122D          

 35 39  0  0  0  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1533004231521122D          

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    0.2366    1.0850    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0579    1.1626    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5800    1.8351    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9282    0.2572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4061    0.9297    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2716   -0.4929    0.0000 C   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
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  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
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 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
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 16 20  1  0  0  0  0
 11 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 10 23  1  0  0  0  0
 23 24  1  0  0  0  0
 23 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 27 29  1  0  0  0  0
 29 30  2  0  0  0  0
 30 31  1  0  0  0  0
  8 31  1  0  0  0  0
 25 31  1  0  0  0  0
 31 32  1  0  0  0  0
 29 33  1  0  0  0  0
 33 34  2  0  0  0  0
 33 35  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0179015

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(O)CC(=O)OC1CC2C3(C)CCCC4(CC4C)C3CCC2(C)C2CC(=O)C(=CC12C)C(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C30H44O5/c1-17-15-30(17)10-7-9-27(4)22(30)8-11-28(5)23-13-21(33)20(19(3)32)16-29(23,6)25(14-24(27)28)35-26(34)12-18(2)31/h16-18,22-25,31H,7-15H2,1-6H3

> <INCHI_KEY>
UBSJGEHBYDKKED-UHFFFAOYSA-N

> <FORMULA>
C30H44O5

> <MOLECULAR_WEIGHT>
484.677

> <EXACT_MASS>
484.318874517

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
79

> <JCHEM_AVERAGE_POLARIZABILITY>
56.10271327498331

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
8-acetyl-2',4a,6a,10b-tetramethyl-9-oxo-3,4,4a,4b,5,6,6a,9,10,10a,10b,11,12,12a-tetradecahydro-2H-spiro[chrysene-1,1'-cyclopropane]-6-yl 3-hydroxybutanoate

> <ALOGPS_LOGP>
4.08

> <JCHEM_LOGP>
4.758390053666668

> <ALOGPS_LOGS>
-5.77

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
18.238476124159593

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.406575072582186

> <JCHEM_PKA_STRONGEST_BASIC>
-2.6206837103202645

> <JCHEM_POLAR_SURFACE_AREA>
80.67

> <JCHEM_REFRACTIVITY>
135.13989999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.23e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
8-acetyl-2',4a,6a,10b-tetramethyl-9-oxo-3,4,4b,5,6,10,10a,11,12,12a-decahydro-2H-spiro[chrysene-1,1'-cyclopropane]-6-yl 3-hydroxybutanoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 23-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-APR-15         0                                  
HETATM    1  C   UNK     0      -3.127   7.046   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.235   5.791   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -2.876   4.391   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      -0.702   5.936   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.191   4.681   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      -0.451   3.281   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0       1.724   4.826   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       2.616   3.570   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.149   3.715   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.041   2.460   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.574   2.605   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.682   3.860   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.215   4.005   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.748   4.150   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       9.641   2.895   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.999   1.495   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      10.400   0.854   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       9.144  -0.038   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       8.503  -1.439   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       7.466   1.350   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       6.825  -0.050   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       5.292  -0.195   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       4.400   1.060   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       3.759  -0.340   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       2.867   0.915   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       2.226  -0.485   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       0.693  -0.630   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       0.052  -2.030   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      -0.199   0.625   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       0.442   2.025   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       1.975   2.170   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       1.083   3.426   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -1.733   0.480   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      -2.625   1.735   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0      -2.374  -0.920   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    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9   31                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   23                                                  
CONECT   11   10   12   13   20                                             
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   18   20                                             
CONECT   17   16   18                                                       
CONECT   18   17   16   19                                                  
CONECT   19   18                                                            
CONECT   20   16   11   21                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   10   24   25                                             
CONECT   24   23                                                            
CONECT   25   23   26   31                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30   33                                                  
CONECT   30   29   31                                                       
CONECT   31   30    8   25   32                                             
CONECT   32   31                                                            
CONECT   33   29   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33                                                            
MASTER        0    0    0    0    0    0    0    0   35    0   78    0
END

View in JSmol

Synonyms

Value	Source
8-Acetyl-3',4a,6a,10b-tetramethyl-9-oxo-3,4,4a,4b,5,6,6a,9,10,10a,10b,11,12,12a-tetradecahydro-2H-spiro[chrysene-1,1'-cyclopropane]-6-yl 3-hydroxybutanoic acid	Generator

Chemical Formula

C₃₀H₄₄O₅

Average Mass

484.6770 Da

Monoisotopic Mass

484.31887 Da

IUPAC Name

8-acetyl-2',4a,6a,10b-tetramethyl-9-oxo-3,4,4a,4b,5,6,6a,9,10,10a,10b,11,12,12a-tetradecahydro-2H-spiro[chrysene-1,1'-cyclopropane]-6-yl 3-hydroxybutanoate

Traditional Name

8-acetyl-2',4a,6a,10b-tetramethyl-9-oxo-3,4,4b,5,6,10,10a,11,12,12a-decahydro-2H-spiro[chrysene-1,1'-cyclopropane]-6-yl 3-hydroxybutanoate

CAS Registry Number

Not Available

SMILES

CC(O)CC(=O)OC1CC2C3(C)CCCC4(CC4C)C3CCC2(C)C2CC(=O)C(=CC12C)C(C)=O

InChI Identifier

InChI=1S/C30H44O5/c1-17-15-30(17)10-7-9-27(4)22(30)8-11-28(5)23-13-21(33)20(19(3)32)16-29(23,6)25(14-24(27)28)35-26(34)12-18(2)31/h16-18,22-25,31H,7-15H2,1-6H3

InChI Key

UBSJGEHBYDKKED-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
Strepsichordaia aliena	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as beta hydroxy acids and derivatives. Beta hydroxy acids and derivatives are compounds containing a carboxylic acid substituted with a hydroxyl group on the C3 carbon atom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Hydroxy acids and derivatives

Sub Class

Beta hydroxy acids and derivatives

Direct Parent

Beta hydroxy acids and derivatives

Alternative Parents

Substituents

Beta-hydroxy acid
Cyclohexenone
Fatty acid ester
Fatty acyl
Carboxylic acid ester
Cyclic ketone
Secondary alcohol
Ketone
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Hydrocarbon derivative
Organic oxide
Alcohol
Carbonyl group
Organic oxygen compound
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	4.08	ALOGPS
logP	4.76	ChemAxon
logS	-5.8	ALOGPS
pKa (Strongest Acidic)	15.41	ChemAxon
pKa (Strongest Basic)	-2.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	80.67 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	135.14 m³·mol⁻¹	ChemAxon
Polarizability	56.1 Å³	ChemAxon
Number of Rings	5	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

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 8-acetyl-2',4a,6a,10b-tetramethyl-9-oxo-3,4,4b,5,6,10,10a,11,12,12a-decahydro-2h-spiro[chrysene-1,1'-cyclopropan]-6-yl 3-hydroxybutanoate (NP0179015)

MOL for NP0179015 (8-acetyl-2',4a,6a,10b-tetramethyl-9-oxo-3,4,4b,5,6,10,10a,11,12,12a-decahydro-2h-spiro[chrysene-1,1'-cyclopropan]-6-yl 3-hydroxybutanoate)

3D MOL for NP0179015 (8-acetyl-2',4a,6a,10b-tetramethyl-9-oxo-3,4,4b,5,6,10,10a,11,12,12a-decahydro-2h-spiro[chrysene-1,1'-cyclopropan]-6-yl 3-hydroxybutanoate)

3D SDF for NP0179015 (8-acetyl-2',4a,6a,10b-tetramethyl-9-oxo-3,4,4b,5,6,10,10a,11,12,12a-decahydro-2h-spiro[chrysene-1,1'-cyclopropan]-6-yl 3-hydroxybutanoate)

3D-SDF for NP0179015 (8-acetyl-2',4a,6a,10b-tetramethyl-9-oxo-3,4,4b,5,6,10,10a,11,12,12a-decahydro-2h-spiro[chrysene-1,1'-cyclopropan]-6-yl 3-hydroxybutanoate)

PDB for NP0179015 (8-acetyl-2',4a,6a,10b-tetramethyl-9-oxo-3,4,4b,5,6,10,10a,11,12,12a-decahydro-2h-spiro[chrysene-1,1'-cyclopropan]-6-yl 3-hydroxybutanoate)

3D PDB for NP0179015 (8-acetyl-2',4a,6a,10b-tetramethyl-9-oxo-3,4,4b,5,6,10,10a,11,12,12a-decahydro-2h-spiro[chrysene-1,1'-cyclopropan]-6-yl 3-hydroxybutanoate)

SMILES for NP0179015 (8-acetyl-2',4a,6a,10b-tetramethyl-9-oxo-3,4,4b,5,6,10,10a,11,12,12a-decahydro-2h-spiro[chrysene-1,1'-cyclopropan]-6-yl 3-hydroxybutanoate)

INCHI for NP0179015 (8-acetyl-2',4a,6a,10b-tetramethyl-9-oxo-3,4,4b,5,6,10,10a,11,12,12a-decahydro-2h-spiro[chrysene-1,1'-cyclopropan]-6-yl 3-hydroxybutanoate)

Structure for NP0179015 (8-acetyl-2',4a,6a,10b-tetramethyl-9-oxo-3,4,4b,5,6,10,10a,11,12,12a-decahydro-2h-spiro[chrysene-1,1'-cyclopropan]-6-yl 3-hydroxybutanoate)

3D Structure for NP0179015 (8-acetyl-2',4a,6a,10b-tetramethyl-9-oxo-3,4,4b,5,6,10,10a,11,12,12a-decahydro-2h-spiro[chrysene-1,1'-cyclopropan]-6-yl 3-hydroxybutanoate)