NP-MRD: Showing NP-Card for 1-[(1s,3as,3br,5as,7s,9as,9bs,11ar)-7-{[(2r,4s,5r,6r)-5-amino-4-methoxy-6-methyloxan-2-yl]oxy}-3a-hydroxy-9a,11a-dimethyl-tetradecahydrocyclopenta[a]phenanthren-1-yl]ethanone (NP0195889)

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Record Information

Version

2.0

Created at

2022-09-04 13:50:26 UTC

Updated at

2022-09-04 13:50:26 UTC

NP-MRD ID

NP0195889

Secondary Accession Numbers

None

Natural Product Identification

Common Name

1-[(1s,3as,3br,5as,7s,9as,9bs,11ar)-7-{[(2r,4s,5r,6r)-5-amino-4-methoxy-6-methyloxan-2-yl]oxy}-3a-hydroxy-9a,11a-dimethyl-tetradecahydrocyclopenta[a]phenanthren-1-yl]ethanone

Description

N-demethylholacurtine belongs to the class of organic compounds known as steroidal glycosides. These are sterol lipids containing a carbohydrate moiety glycosidically linked to the steroid skeleton. 1-[(1s,3as,3br,5as,7s,9as,9bs,11ar)-7-{[(2r,4s,5r,6r)-5-amino-4-methoxy-6-methyloxan-2-yl]oxy}-3a-hydroxy-9a,11a-dimethyl-tetradecahydrocyclopenta[a]phenanthren-1-yl]ethanone is found in Holarrhena curtisii. 1-[(1s,3as,3br,5as,7s,9as,9bs,11ar)-7-{[(2r,4s,5r,6r)-5-amino-4-methoxy-6-methyloxan-2-yl]oxy}-3a-hydroxy-9a,11a-dimethyl-tetradecahydrocyclopenta[a]phenanthren-1-yl]ethanone was first documented in 1998 (PMID: 9834146). Based on a literature review very few articles have been published on N-demethylholacurtine.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309042215502D          

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M  END

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M  END


  Mrv1652309042215502D          

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    5.9193    1.1884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0117    2.1096    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2920    2.8855    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.7602    3.5162    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1041    3.0307    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.3844    3.8066    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  3  2  1  1  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  6  0  0  0
  7  6  1  1  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  1  0  0  0
 10 12  1  0  0  0  0
 12 13  1  1  0  0  0
 13 14  1  0  0  0  0
 15 14  1  6  0  0  0
 15 16  1  0  0  0  0
 10 16  1  0  0  0  0
 16 17  1  1  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  1  0  0  0
 19 21  1  0  0  0  0
 21 22  1  1  0  0  0
 22 23  1  0  0  0  0
 22 24  2  0  0  0  0
 21 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 15 27  1  0  0  0  0
 19 27  1  0  0  0  0
 27 28  1  1  0  0  0
 12 29  1  0  0  0  0
  7 29  1  0  0  0  0
  5 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  6  0  0  0
 31 33  1  0  0  0  0
  3 33  1  0  0  0  0
 33 34  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0195889

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CO[C@H]1C[C@H](O[C@H]2CC[C@@]3(C)[C@@H](CC[C@@H]4[C@@H]3CC[C@]3(C)[C@H](CC[C@]43O)C(C)=O)C2)O[C@H](C)[C@H]1N

> <INCHI_IDENTIFIER>
InChI=1S/C28H47NO5/c1-16(30)20-10-13-28(31)22-7-6-18-14-19(34-24-15-23(32-5)25(29)17(2)33-24)8-11-26(18,3)21(22)9-12-27(20,28)4/h17-25,31H,6-15,29H2,1-5H3/t17-,18+,19+,20-,21+,22-,23+,24+,25-,26+,27-,28+/m1/s1

> <INCHI_KEY>
XNPZZOKPHOMJPJ-KLVKTECBSA-N

> <FORMULA>
C28H47NO5

> <MOLECULAR_WEIGHT>
477.686

> <EXACT_MASS>
477.345423617

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
81

> <JCHEM_AVERAGE_POLARIZABILITY>
55.57745500483645

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
1-[(1S,2S,5S,7S,10R,11S,14S,15R)-5-{[(2R,4S,5R,6R)-5-amino-4-methoxy-6-methyloxan-2-yl]oxy}-11-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]ethan-1-one

> <JCHEM_LOGP>
3.61854899

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
18.846055398424042

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.15830356832829

> <JCHEM_PKA_STRONGEST_BASIC>
9.133373253458648

> <JCHEM_POLAR_SURFACE_AREA>
91.01

> <JCHEM_REFRACTIVITY>
130.12539999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
1-[(1S,2S,5S,7S,10R,11S,14S,15R)-5-{[(2R,4S,5R,6R)-5-amino-4-methoxy-6-methyloxan-2-yl]oxy}-11-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]ethanone

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-22         0                                  
HETATM    1  C   UNK     0      18.160   6.199   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      17.636   4.751   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      16.120   4.480   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      15.597   3.032   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      14.081   2.761   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      13.558   1.312   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      12.042   1.041   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      11.519  -0.407   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      10.003  -0.678   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.010   0.499   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.487  -0.949   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       9.533   1.947   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.541   3.125   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.025   2.854   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.502   1.405   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       7.494   0.228   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.971  -1.221   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.455  -1.492   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.462  -0.314   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       3.791  -1.700   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.923  -0.264   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       1.978  -1.480   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       2.558  -2.907   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       0.452  -1.269   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       2.495   1.215   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       3.770   2.079   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       4.986   1.134   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       5.355   2.629   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      11.049   2.218   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      13.089   3.938   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      13.612   5.386   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      12.619   6.564   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      15.128   5.657   0.000  0.00  0.00           C+0
HETATM   34  N   UNK     0      15.651   7.106   0.000  0.00  0.00           N+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   33                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   30                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   29                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   12   16                                             
CONECT   11   10                                                            
CONECT   12   10   13   29                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   27                                                  
CONECT   16   15   10   17                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   21   27                                             
CONECT   20   19                                                            
CONECT   21   19   22   25                                                  
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22                                                            
CONECT   25   21   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   15   19   28                                             
CONECT   28   27                                                            
CONECT   29   12    7                                                       
CONECT   30    5   31                                                       
CONECT   31   30   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31    3   34                                                  
CONECT   34   33                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   76    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₈H₄₇NO₅

Average Mass

477.6860 Da

Monoisotopic Mass

477.34542 Da

IUPAC Name

1-[(1S,2S,5S,7S,10R,11S,14S,15R)-5-{[(2R,4S,5R,6R)-5-amino-4-methoxy-6-methyloxan-2-yl]oxy}-11-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]ethan-1-one

Traditional Name

1-[(1S,2S,5S,7S,10R,11S,14S,15R)-5-{[(2R,4S,5R,6R)-5-amino-4-methoxy-6-methyloxan-2-yl]oxy}-11-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]ethanone

CAS Registry Number

Not Available

SMILES

CO[C@H]1C[C@H](O[C@H]2CC[C@@]3(C)[C@@H](CC[C@@H]4[C@@H]3CC[C@]3(C)[C@H](CC[C@]43O)C(C)=O)C2)O[C@H](C)[C@H]1N

InChI Identifier

InChI=1S/C28H47NO5/c1-16(30)20-10-13-28(31)22-7-6-18-14-19(34-24-15-23(32-5)25(29)17(2)33-24)8-11-26(18,3)21(22)9-12-27(20,28)4/h17-25,31H,6-15,29H2,1-5H3/t17-,18+,19+,20-,21+,22-,23+,24+,25-,26+,27-,28+/m1/s1

InChI Key

XNPZZOKPHOMJPJ-KLVKTECBSA-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
Holarrhena curtisii	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as steroidal glycosides. These are sterol lipids containing a carbohydrate moiety glycosidically linked to the steroid skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Steroidal glycosides

Direct Parent

Steroidal glycosides

Alternative Parents

Substituents

Steroidal glycoside
20-oxosteroid
Pregnane-skeleton
Aminoglycoside core
14-hydroxysteroid
Hydroxysteroid
Oxosteroid
Amino saccharide
Oxane
Tertiary alcohol
Cyclic alcohol
Ketone
Oxacycle
Organoheterocyclic compound
Dialkyl ether
Acetal
Ether
Primary amine
Primary aliphatic amine
Organonitrogen compound
Organopnictogen compound
Organic oxygen compound
Organooxygen compound
Organic oxide
Hydrocarbon derivative
Carbonyl group
Organic nitrogen compound
Amine
Alcohol
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic 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	3.62	ChemAxon
pKa (Strongest Acidic)	14.16	ChemAxon
pKa (Strongest Basic)	9.13	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	91.01 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	130.13 m³·mol⁻¹	ChemAxon
Polarizability	55.58 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

C00050174

Chemspider ID

8158079

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

9982489

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Kam TS, Sim KM, Koyano T, Toyoshima M, Hayashi M, Komiyama K: Cytotoxic and leishmanicidal aminoglycosteroids and aminosteroids from Holarrhena curtisii. J Nat Prod. 1998 Nov;61(11):1332-6. doi: 10.1021/np970545f. [PubMed:9834146 ]
LOTUS database [Link]

Showing NP-Card for 1-[(1s,3as,3br,5as,7s,9as,9bs,11ar)-7-{[(2r,4s,5r,6r)-5-amino-4-methoxy-6-methyloxan-2-yl]oxy}-3a-hydroxy-9a,11a-dimethyl-tetradecahydrocyclopenta[a]phenanthren-1-yl]ethanone (NP0195889)

MOL for NP0195889 (1-[(1s,3as,3br,5as,7s,9as,9bs,11ar)-7-{[(2r,4s,5r,6r)-5-amino-4-methoxy-6-methyloxan-2-yl]oxy}-3a-hydroxy-9a,11a-dimethyl-tetradecahydrocyclopenta[a]phenanthren-1-yl]ethanone)

3D MOL for NP0195889 (1-[(1s,3as,3br,5as,7s,9as,9bs,11ar)-7-{[(2r,4s,5r,6r)-5-amino-4-methoxy-6-methyloxan-2-yl]oxy}-3a-hydroxy-9a,11a-dimethyl-tetradecahydrocyclopenta[a]phenanthren-1-yl]ethanone)

3D SDF for NP0195889 (1-[(1s,3as,3br,5as,7s,9as,9bs,11ar)-7-{[(2r,4s,5r,6r)-5-amino-4-methoxy-6-methyloxan-2-yl]oxy}-3a-hydroxy-9a,11a-dimethyl-tetradecahydrocyclopenta[a]phenanthren-1-yl]ethanone)

3D-SDF for NP0195889 (1-[(1s,3as,3br,5as,7s,9as,9bs,11ar)-7-{[(2r,4s,5r,6r)-5-amino-4-methoxy-6-methyloxan-2-yl]oxy}-3a-hydroxy-9a,11a-dimethyl-tetradecahydrocyclopenta[a]phenanthren-1-yl]ethanone)

PDB for NP0195889 (1-[(1s,3as,3br,5as,7s,9as,9bs,11ar)-7-{[(2r,4s,5r,6r)-5-amino-4-methoxy-6-methyloxan-2-yl]oxy}-3a-hydroxy-9a,11a-dimethyl-tetradecahydrocyclopenta[a]phenanthren-1-yl]ethanone)

3D PDB for NP0195889 (1-[(1s,3as,3br,5as,7s,9as,9bs,11ar)-7-{[(2r,4s,5r,6r)-5-amino-4-methoxy-6-methyloxan-2-yl]oxy}-3a-hydroxy-9a,11a-dimethyl-tetradecahydrocyclopenta[a]phenanthren-1-yl]ethanone)

SMILES for NP0195889 (1-[(1s,3as,3br,5as,7s,9as,9bs,11ar)-7-{[(2r,4s,5r,6r)-5-amino-4-methoxy-6-methyloxan-2-yl]oxy}-3a-hydroxy-9a,11a-dimethyl-tetradecahydrocyclopenta[a]phenanthren-1-yl]ethanone)

INCHI for NP0195889 (1-[(1s,3as,3br,5as,7s,9as,9bs,11ar)-7-{[(2r,4s,5r,6r)-5-amino-4-methoxy-6-methyloxan-2-yl]oxy}-3a-hydroxy-9a,11a-dimethyl-tetradecahydrocyclopenta[a]phenanthren-1-yl]ethanone)

Structure for NP0195889 (1-[(1s,3as,3br,5as,7s,9as,9bs,11ar)-7-{[(2r,4s,5r,6r)-5-amino-4-methoxy-6-methyloxan-2-yl]oxy}-3a-hydroxy-9a,11a-dimethyl-tetradecahydrocyclopenta[a]phenanthren-1-yl]ethanone)

3D Structure for NP0195889 (1-[(1s,3as,3br,5as,7s,9as,9bs,11ar)-7-{[(2r,4s,5r,6r)-5-amino-4-methoxy-6-methyloxan-2-yl]oxy}-3a-hydroxy-9a,11a-dimethyl-tetradecahydrocyclopenta[a]phenanthren-1-yl]ethanone)