NP-MRD: Showing NP-Card for 1,2-bis(acetyloxy)-6-hydroxy-7-isopropyl-1,4a-dimethyl-2,3,4,9,10,10a-hexahydrophenanthren-9-yl acetate (NP0259056)

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Record Information

Version

2.0

Created at

2022-09-08 00:47:42 UTC

Updated at

2022-09-08 00:47:42 UTC

NP-MRD ID

NP0259056

Secondary Accession Numbers

None

Natural Product Identification

Common Name

1,2-bis(acetyloxy)-6-hydroxy-7-isopropyl-1,4a-dimethyl-2,3,4,9,10,10a-hexahydrophenanthren-9-yl acetate

Description

1,9-Bis(acetyloxy)-6-hydroxy-1,4a-dimethyl-7-(propan-2-yl)-1,2,3,4,4a,9,10,10a-octahydrophenanthren-2-yl acetate belongs to the class of organic compounds known as 16-oxosteroids. These are steroid derivatives carrying a C=O group at the 16-position of the steroid skeleton. 1,9-Bis(acetyloxy)-6-hydroxy-1,4a-dimethyl-7-(propan-2-yl)-1,2,3,4,4a,9,10,10a-octahydrophenanthren-2-yl acetate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004251507022D          

 32 34  0  0  0  0            999 V2000
    0.7954   -1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2079   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7954   -0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0329   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4454   -0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2704   -0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6829    0.6039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    5.7454   -0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    6.5206    0.1716    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6639    0.9841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0319    1.5144    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

     RDKit          3D

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M  END


  Mrv1533004251507022D          

 32 34  0  0  0  0            999 V2000
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M  END
> <DATABASE_ID>
NP0259056

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)C1=CC2=C(C=C1O)C1(C)CCC(OC(C)=O)C(C)(OC(C)=O)C1CC2OC(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C25H34O7/c1-13(2)17-10-18-19(11-20(17)29)24(6)9-8-23(31-15(4)27)25(7,32-16(5)28)22(24)12-21(18)30-14(3)26/h10-11,13,21-23,29H,8-9,12H2,1-7H3

> <INCHI_KEY>
RYHLIIWRCPVHRD-UHFFFAOYSA-N

> <FORMULA>
C25H34O7

> <MOLECULAR_WEIGHT>
446.54

> <EXACT_MASS>
446.230453435

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
66

> <JCHEM_AVERAGE_POLARIZABILITY>
49.4218204897883

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1,2-bis(acetyloxy)-6-hydroxy-1,4a-dimethyl-7-(propan-2-yl)-1,2,3,4,4a,9,10,10a-octahydrophenanthren-9-yl acetate

> <ALOGPS_LOGP>
4.33

> <JCHEM_LOGP>
3.655914019333334

> <ALOGPS_LOGS>
-5.03

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.8633973984289

> <JCHEM_PKA_STRONGEST_BASIC>
-5.721807208782722

> <JCHEM_POLAR_SURFACE_AREA>
99.13000000000002

> <JCHEM_REFRACTIVITY>
117.24619999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.16e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1,2-bis(acetyloxy)-6-hydroxy-7-isopropyl-1,4a-dimethyl-2,3,4,9,10,10a-hexahydrophenanthren-9-yl acetate

> <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       1.485  -2.874   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.255  -1.540   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.485  -0.206   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.795  -1.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.565  -0.206   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.105  -0.206   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.875   1.127   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.415   1.127   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.185  -0.206   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      10.725  -0.206   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      10.457   1.310   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      12.172   0.320   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      12.439   1.837   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      11.260   2.827   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      13.886   2.364   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      11.495  -1.540   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      10.725  -2.874   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       9.185  -2.874   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       8.415  -1.540   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       7.645  -2.874   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       6.875  -1.540   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       6.105  -2.874   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       4.565  -2.874   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       3.795  -4.207   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0      13.035  -1.540   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      13.805  -2.874   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      15.345  -2.874   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      13.035  -4.207   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       6.105   2.461   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       4.565   2.461   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       3.795   1.127   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       3.795   3.795   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5   23                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7   21                                                  
CONECT    7    6    8   29                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   19                                                  
CONECT   10    9   11   12   16                                             
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13                                                            
CONECT   16   10   17   25                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18    9   20   21                                             
CONECT   20   19                                                            
CONECT   21   19    6   22                                                  
CONECT   22   21   23                                                       
CONECT   23   22    4   24                                                  
CONECT   24   23                                                            
CONECT   25   16   26                                                       
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26                                                            
CONECT   29    7   30                                                       
CONECT   30   29   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30                                                            
MASTER        0    0    0    0    0    0    0    0   32    0   68    0
END

View in JSmol

Synonyms

Value	Source
1,9-Bis(acetyloxy)-6-hydroxy-1,4a-dimethyl-7-(propan-2-yl)-1,2,3,4,4a,9,10,10a-octahydrophenanthren-2-yl acetic acid	Generator

Chemical Formula

C₂₅H₃₄O₇

Average Mass

446.5400 Da

Monoisotopic Mass

446.23045 Da

IUPAC Name

1,2-bis(acetyloxy)-6-hydroxy-1,4a-dimethyl-7-(propan-2-yl)-1,2,3,4,4a,9,10,10a-octahydrophenanthren-9-yl acetate

Traditional Name

1,2-bis(acetyloxy)-6-hydroxy-7-isopropyl-1,4a-dimethyl-2,3,4,9,10,10a-hexahydrophenanthren-9-yl acetate

CAS Registry Number

Not Available

SMILES

CC(C)C1=CC2=C(C=C1O)C1(C)CCC(OC(C)=O)C(C)(OC(C)=O)C1CC2OC(C)=O

InChI Identifier

InChI=1S/C25H34O7/c1-13(2)17-10-18-19(11-20(17)29)24(6)9-8-23(31-15(4)27)25(7,32-16(5)28)22(24)12-21(18)30-14(3)26/h10-11,13,21-23,29H,8-9,12H2,1-7H3

InChI Key

RYHLIIWRCPVHRD-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

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 16-oxosteroids. These are steroid derivatives carrying a C=O group at the 16-position of the steroid skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Oxosteroids

Direct Parent

16-oxosteroids

Alternative Parents

Substituents

Abietane diterpenoid
Diterpenoid
2-hydroxysteroid
Hydroxysteroid
16-oxosteroid
Hydrophenanthrene
Phenanthrene
Tetralin
Tricarboxylic acid or derivatives
1-hydroxy-2-unsubstituted benzenoid
Benzenoid
Carboxylic acid ester
Carboxylic acid derivative
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Carbonyl group
Aromatic homopolycyclic compound

Molecular Framework

Aromatic 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	4.33	ALOGPS
logP	3.66	ChemAxon
logS	-5	ALOGPS
pKa (Strongest Acidic)	9.86	ChemAxon
pKa (Strongest Basic)	-5.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	99.13 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	117.25 m³·mol⁻¹	ChemAxon
Polarizability	49.42 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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

75306407

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 1,2-bis(acetyloxy)-6-hydroxy-7-isopropyl-1,4a-dimethyl-2,3,4,9,10,10a-hexahydrophenanthren-9-yl acetate (NP0259056)

MOL for NP0259056 (1,2-bis(acetyloxy)-6-hydroxy-7-isopropyl-1,4a-dimethyl-2,3,4,9,10,10a-hexahydrophenanthren-9-yl acetate)

3D MOL for NP0259056 (1,2-bis(acetyloxy)-6-hydroxy-7-isopropyl-1,4a-dimethyl-2,3,4,9,10,10a-hexahydrophenanthren-9-yl acetate)

3D SDF for NP0259056 (1,2-bis(acetyloxy)-6-hydroxy-7-isopropyl-1,4a-dimethyl-2,3,4,9,10,10a-hexahydrophenanthren-9-yl acetate)

3D-SDF for NP0259056 (1,2-bis(acetyloxy)-6-hydroxy-7-isopropyl-1,4a-dimethyl-2,3,4,9,10,10a-hexahydrophenanthren-9-yl acetate)

PDB for NP0259056 (1,2-bis(acetyloxy)-6-hydroxy-7-isopropyl-1,4a-dimethyl-2,3,4,9,10,10a-hexahydrophenanthren-9-yl acetate)

3D PDB for NP0259056 (1,2-bis(acetyloxy)-6-hydroxy-7-isopropyl-1,4a-dimethyl-2,3,4,9,10,10a-hexahydrophenanthren-9-yl acetate)

SMILES for NP0259056 (1,2-bis(acetyloxy)-6-hydroxy-7-isopropyl-1,4a-dimethyl-2,3,4,9,10,10a-hexahydrophenanthren-9-yl acetate)

INCHI for NP0259056 (1,2-bis(acetyloxy)-6-hydroxy-7-isopropyl-1,4a-dimethyl-2,3,4,9,10,10a-hexahydrophenanthren-9-yl acetate)

Structure for NP0259056 (1,2-bis(acetyloxy)-6-hydroxy-7-isopropyl-1,4a-dimethyl-2,3,4,9,10,10a-hexahydrophenanthren-9-yl acetate)

3D Structure for NP0259056 (1,2-bis(acetyloxy)-6-hydroxy-7-isopropyl-1,4a-dimethyl-2,3,4,9,10,10a-hexahydrophenanthren-9-yl acetate)