NP-MRD: Showing NP-Card for 6-hydroxy-7-(2-hydroxypropan-2-yl)-9b-methyl-3h,3bh,4h,5h,10h,11h-phenanthro[1,2-c]furan-1-one (NP0220796)

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Record Information

Version

2.0

Created at

2022-09-05 22:12:33 UTC

Updated at

2022-09-05 22:12:33 UTC

NP-MRD ID

NP0220796

Secondary Accession Numbers

None

Natural Product Identification

Common Name

6-hydroxy-7-(2-hydroxypropan-2-yl)-9b-methyl-3h,3bh,4h,5h,10h,11h-phenanthro[1,2-c]furan-1-one

Description

SCHEMBL9359741 belongs to the class of organic compounds known as oxosteroids. These are steroid derivatives carrying a C=O group attached to steroid skeleton. 6-hydroxy-7-(2-hydroxypropan-2-yl)-9b-methyl-3h,3bh,4h,5h,10h,11h-phenanthro[1,2-c]furan-1-one is found in Tripterygium wilfordii. Based on a literature review very few articles have been published on SCHEMBL9359741.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309062200122D          

 24 27  0  0  0  0            999 V2000
    0.4215   -0.3894    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2336   -0.5346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0884   -1.3467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3789    0.2775    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0458   -0.6798    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3261   -1.4557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1382   -1.6009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6700   -0.9702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3897   -0.1943    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5776   -0.0491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2973    0.7268    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9215    0.4364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7336    0.2912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0139   -0.4847    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8261   -0.6299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1064   -1.4059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5745   -2.0366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7624   -1.8914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4821   -1.1154    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9503   -1.7461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9309   -1.3791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4373   -2.0304    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1602   -0.5866    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4774   -0.1236    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
  2  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  5 10  1  0  0  0  0
 10 11  1  0  0  0  0
  9 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  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  1  0  0  0  0
 18 19  1  0  0  0  0
  8 19  1  0  0  0  0
 14 19  1  0  0  0  0
 19 20  1  0  0  0  0
 16 21  1  0  0  0  0
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
 15 24  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0220796

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)(O)C1=CC=C2C(CCC3C4=C(CCC23C)C(=O)OC4)=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C20H24O4/c1-19(2,23)16-7-6-14-12(17(16)21)4-5-15-13-10-24-18(22)11(13)8-9-20(14,15)3/h6-7,15,21,23H,4-5,8-10H2,1-3H3

> <INCHI_KEY>
IJRYPWHSZRRHHZ-UHFFFAOYSA-N

> <FORMULA>
C20H24O4

> <MOLECULAR_WEIGHT>
328.408

> <EXACT_MASS>
328.167459253

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
48

> <JCHEM_AVERAGE_POLARIZABILITY>
36.30618900847967

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
6-hydroxy-5-(2-hydroxypropan-2-yl)-1-methyl-13-oxatetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-2,4,6,11(15)-tetraen-14-one

> <JCHEM_LOGP>
3.2847601529999992

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.187840751388375

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.178430363394794

> <JCHEM_PKA_STRONGEST_BASIC>
-3.051184289361273

> <JCHEM_POLAR_SURFACE_AREA>
66.76

> <JCHEM_REFRACTIVITY>
92.04639999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
6-hydroxy-5-(2-hydroxypropan-2-yl)-1-methyl-13-oxatetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-2,4,6,11(15)-tetraen-14-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-SEP-22         0                                  
HETATM    1  C   UNK     0       0.787  -0.727   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.303  -0.998   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.032  -2.514   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       2.574   0.518   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       3.819  -1.269   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.342  -2.717   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.858  -2.988   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.851  -1.811   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.327  -0.363   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.811  -0.092   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       4.288   1.357   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       7.320   0.815   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.836   0.544   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.359  -0.905   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      10.875  -1.176   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      11.399  -2.624   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      10.406  -3.802   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.890  -3.531   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       8.367  -2.082   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       7.374  -3.259   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      12.938  -2.574   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      13.883  -3.790   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      13.366  -1.095   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      12.091  -0.231   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4    5                                             
CONECT    3    2                                                            
CONECT    4    2                                                            
CONECT    5    2    6   10                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   19                                                  
CONECT    9    8   10   12                                                  
CONECT   10    9    5   11                                                  
CONECT   11   10                                                            
CONECT   12    9   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   19                                                  
CONECT   15   14   16   24                                                  
CONECT   16   15   17   21                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18    8   14   20                                             
CONECT   20   19                                                            
CONECT   21   16   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24                                                       
CONECT   24   23   15                                                       
MASTER        0    0    0    0    0    0    0    0   24    0   54    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₀H₂₄O₄

Average Mass

328.4080 Da

Monoisotopic Mass

328.16746 Da

IUPAC Name

6-hydroxy-5-(2-hydroxypropan-2-yl)-1-methyl-13-oxatetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-2,4,6,11(15)-tetraen-14-one

Traditional Name

6-hydroxy-5-(2-hydroxypropan-2-yl)-1-methyl-13-oxatetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-2,4,6,11(15)-tetraen-14-one

CAS Registry Number

Not Available

SMILES

CC(C)(O)C1=CC=C2C(CCC3C4=C(CCC23C)C(=O)OC4)=C1O

InChI Identifier

InChI=1S/C20H24O4/c1-19(2,23)16-7-6-14-12(17(16)21)4-5-15-13-10-24-18(22)11(13)8-9-20(14,15)3/h6-7,15,21,23H,4-5,8-10H2,1-3H3

InChI Key

IJRYPWHSZRRHHZ-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
Tripterygium wilfordii	LOTUS Database	35616633

Chemical Taxonomy

Description

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

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Oxosteroids

Direct Parent

Oxosteroids

Alternative Parents

Substituents

4-hydroxysteroid
Hydroxysteroid
17-oxosteroid
Oxosteroid
16-oxasteroid
Phenanthrene
Tetralin
1-hydroxy-4-unsubstituted benzenoid
Phenol
Benzenoid
2-furanone
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Tertiary alcohol
Dihydrofuran
Carboxylic acid ester
Lactone
Monocarboxylic acid or derivatives
Organoheterocyclic compound
Carboxylic acid derivative
Oxacycle
Organooxygen compound
Organic oxygen compound
Alcohol
Aromatic alcohol
Hydrocarbon derivative
Organic oxide
Carbonyl group
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	3.28	ChemAxon
pKa (Strongest Acidic)	10.18	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	66.76 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	92.05 m³·mol⁻¹	ChemAxon
Polarizability	36.31 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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

14418869

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

19775901

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 6-hydroxy-7-(2-hydroxypropan-2-yl)-9b-methyl-3h,3bh,4h,5h,10h,11h-phenanthro[1,2-c]furan-1-one (NP0220796)

MOL for NP0220796 (6-hydroxy-7-(2-hydroxypropan-2-yl)-9b-methyl-3h,3bh,4h,5h,10h,11h-phenanthro[1,2-c]furan-1-one)

3D MOL for NP0220796 (6-hydroxy-7-(2-hydroxypropan-2-yl)-9b-methyl-3h,3bh,4h,5h,10h,11h-phenanthro[1,2-c]furan-1-one)

3D SDF for NP0220796 (6-hydroxy-7-(2-hydroxypropan-2-yl)-9b-methyl-3h,3bh,4h,5h,10h,11h-phenanthro[1,2-c]furan-1-one)

3D-SDF for NP0220796 (6-hydroxy-7-(2-hydroxypropan-2-yl)-9b-methyl-3h,3bh,4h,5h,10h,11h-phenanthro[1,2-c]furan-1-one)

PDB for NP0220796 (6-hydroxy-7-(2-hydroxypropan-2-yl)-9b-methyl-3h,3bh,4h,5h,10h,11h-phenanthro[1,2-c]furan-1-one)

3D PDB for NP0220796 (6-hydroxy-7-(2-hydroxypropan-2-yl)-9b-methyl-3h,3bh,4h,5h,10h,11h-phenanthro[1,2-c]furan-1-one)

SMILES for NP0220796 (6-hydroxy-7-(2-hydroxypropan-2-yl)-9b-methyl-3h,3bh,4h,5h,10h,11h-phenanthro[1,2-c]furan-1-one)

INCHI for NP0220796 (6-hydroxy-7-(2-hydroxypropan-2-yl)-9b-methyl-3h,3bh,4h,5h,10h,11h-phenanthro[1,2-c]furan-1-one)

Structure for NP0220796 (6-hydroxy-7-(2-hydroxypropan-2-yl)-9b-methyl-3h,3bh,4h,5h,10h,11h-phenanthro[1,2-c]furan-1-one)

3D Structure for NP0220796 (6-hydroxy-7-(2-hydroxypropan-2-yl)-9b-methyl-3h,3bh,4h,5h,10h,11h-phenanthro[1,2-c]furan-1-one)