NP-MRD: Showing NP-Card for 1-(furan-3-yl)-3,5,10-trihydroxy-3a,3b,6,6,9a-pentamethyl-2h,3h,9bh,10h,11h-cyclopenta[a]phenanthrene-4,7-dione (NP0299170)

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Record Information

Version

2.0

Created at

2022-09-10 10:51:04 UTC

Updated at

2022-09-10 10:51:05 UTC

NP-MRD ID

NP0299170

Secondary Accession Numbers

None

Natural Product Identification

Common Name

1-(furan-3-yl)-3,5,10-trihydroxy-3a,3b,6,6,9a-pentamethyl-2h,3h,9bh,10h,11h-cyclopenta[a]phenanthrene-4,7-dione

Description

14-(Furan-3-yl)-8,12,17-trihydroxy-2,6,6,10,11-pentamethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadeca-3,7,14-triene-5,9-dione belongs to the class of organic compounds known as 17-furanylsteroids and derivatives. These are steroidal compounds having a furanyl group linked to the steroid backbone at the C17 position. 1-(furan-3-yl)-3,5,10-trihydroxy-3a,3b,6,6,9a-pentamethyl-2h,3h,9bh,10h,11h-cyclopenta[a]phenanthrene-4,7-dione is found in Walsura robusta. 14-(Furan-3-yl)-8,12,17-trihydroxy-2,6,6,10,11-pentamethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadeca-3,7,14-triene-5,9-dione is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004241516422D          

 32 36  0  0  0  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1533004241516422D          

 32 36  0  0  0  0            999 V2000
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M  END
> <DATABASE_ID>
NP0299170

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC12C(O)CC(C3=COC=C3)=C1CC(O)C1C3(C)C=CC(=O)C(C)(C)C3=C(O)C(=O)C21C

> <INCHI_IDENTIFIER>
InChI=1S/C26H30O6/c1-23(2)17(28)6-8-24(3)20-16(27)11-15-14(13-7-9-32-12-13)10-18(29)25(15,4)26(20,5)22(31)19(30)21(23)24/h6-9,12,16,18,20,27,29-30H,10-11H2,1-5H3

> <INCHI_KEY>
XXFWAJSCCSMNPP-UHFFFAOYSA-N

> <FORMULA>
C26H30O6

> <MOLECULAR_WEIGHT>
438.52

> <EXACT_MASS>
438.204238686

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
62

> <JCHEM_AVERAGE_POLARIZABILITY>
46.63391308043092

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
14-(furan-3-yl)-8,12,17-trihydroxy-2,6,6,10,11-pentamethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-3,7,14-triene-5,9-dione

> <ALOGPS_LOGP>
2.71

> <JCHEM_LOGP>
2.5181532646666662

> <ALOGPS_LOGS>
-3.79

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.354868458640887

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.414873364028091

> <JCHEM_PKA_STRONGEST_BASIC>
-2.848031884365993

> <JCHEM_POLAR_SURFACE_AREA>
107.97

> <JCHEM_REFRACTIVITY>
121.0672

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.17e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
14-(furan-3-yl)-8,12,17-trihydroxy-2,6,6,10,11-pentamethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-3,7,14-triene-5,9-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-APR-15         0                                  
HETATM    1  C   UNK     0      -0.521  -6.072   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.810  -5.298   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.341  -6.744   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.182  -4.121   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      -1.698  -4.392   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       0.341  -2.673   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.857  -2.402   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.850  -3.579   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.373  -2.131   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.366  -3.308   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.889  -1.859   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       3.896  -0.682   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       6.405  -1.588   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.398  -2.766   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.937  -2.816   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       9.365  -4.295   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.090  -5.159   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       8.040  -6.698   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       6.874  -4.214   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.505  -5.709   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       5.358  -4.485   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       5.939  -5.912   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       4.835  -5.934   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       5.828  -7.111   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       3.319  -6.205   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       2.326  -5.027   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       2.796  -7.653   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       9.882  -1.600   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       9.454  -0.121   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      10.728   0.744   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      11.944  -0.202   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      11.421  -1.650   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4   26                                             
CONECT    3    2                                                            
CONECT    4    2    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   10   26                                             
CONECT    9    8                                                            
CONECT   10    8   11   21                                                  
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13   15   19                                                  
CONECT   15   14   16   28                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   14   20   21                                             
CONECT   20   19                                                            
CONECT   21   19   10   22   23                                             
CONECT   22   21                                                            
CONECT   23   21   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26   27                                                  
CONECT   26   25    2    8                                                  
CONECT   27   25                                                            
CONECT   28   15   29   32                                                  
CONECT   29   28   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   28                                                       
MASTER        0    0    0    0    0    0    0    0   32    0   72    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₆H₃₀O₆

Average Mass

438.5200 Da

Monoisotopic Mass

438.20424 Da

IUPAC Name

14-(furan-3-yl)-8,12,17-trihydroxy-2,6,6,10,11-pentamethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-3,7,14-triene-5,9-dione

Traditional Name

14-(furan-3-yl)-8,12,17-trihydroxy-2,6,6,10,11-pentamethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-3,7,14-triene-5,9-dione

CAS Registry Number

Not Available

SMILES

CC12C(O)CC(C3=COC=C3)=C1CC(O)C1C3(C)C=CC(=O)C(C)(C)C3=C(O)C(=O)C21C

InChI Identifier

InChI=1S/C26H30O6/c1-23(2)17(28)6-8-24(3)20-16(27)11-15-14(13-7-9-32-12-13)10-18(29)25(15,4)26(20,5)22(31)19(30)21(23)24/h6-9,12,16,18,20,27,29-30H,10-11H2,1-5H3

InChI Key

XXFWAJSCCSMNPP-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
Walsura robusta	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 17-furanylsteroids and derivatives. These are steroidal compounds having a furanyl group linked to the steroid backbone at the C17 position.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

17-furanylsteroids and derivatives

Direct Parent

17-furanylsteroids and derivatives

Alternative Parents

Substituents

17-furanylsteroid skeleton
15-hydroxysteroid
Hydroxysteroid
6-hydroxysteroid
Oxosteroid
11-hydroxysteroid
7-oxosteroid
3-oxosteroid
3-oxo-delta-1-steroid
Delta-1-steroid
Cyclohexenone
Furan
Cyclic alcohol
Heteroaromatic compound
Cyclic ketone
Secondary alcohol
Ketone
Oxacycle
Organoheterocyclic compound
Enol
Polyol
Organic oxygen compound
Carbonyl group
Organic oxide
Hydrocarbon derivative
Alcohol
Organooxygen compound
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	2.71	ALOGPS
logP	2.52	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Acidic)	8.41	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	107.97 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	121.07 m³·mol⁻¹	ChemAxon
Polarizability	46.63 Å³	ChemAxon
Number of Rings	5	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

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

73311290

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 1-(furan-3-yl)-3,5,10-trihydroxy-3a,3b,6,6,9a-pentamethyl-2h,3h,9bh,10h,11h-cyclopenta[a]phenanthrene-4,7-dione (NP0299170)

MOL for NP0299170 (1-(furan-3-yl)-3,5,10-trihydroxy-3a,3b,6,6,9a-pentamethyl-2h,3h,9bh,10h,11h-cyclopenta[a]phenanthrene-4,7-dione)

3D MOL for NP0299170 (1-(furan-3-yl)-3,5,10-trihydroxy-3a,3b,6,6,9a-pentamethyl-2h,3h,9bh,10h,11h-cyclopenta[a]phenanthrene-4,7-dione)

3D SDF for NP0299170 (1-(furan-3-yl)-3,5,10-trihydroxy-3a,3b,6,6,9a-pentamethyl-2h,3h,9bh,10h,11h-cyclopenta[a]phenanthrene-4,7-dione)

3D-SDF for NP0299170 (1-(furan-3-yl)-3,5,10-trihydroxy-3a,3b,6,6,9a-pentamethyl-2h,3h,9bh,10h,11h-cyclopenta[a]phenanthrene-4,7-dione)

PDB for NP0299170 (1-(furan-3-yl)-3,5,10-trihydroxy-3a,3b,6,6,9a-pentamethyl-2h,3h,9bh,10h,11h-cyclopenta[a]phenanthrene-4,7-dione)

3D PDB for NP0299170 (1-(furan-3-yl)-3,5,10-trihydroxy-3a,3b,6,6,9a-pentamethyl-2h,3h,9bh,10h,11h-cyclopenta[a]phenanthrene-4,7-dione)

SMILES for NP0299170 (1-(furan-3-yl)-3,5,10-trihydroxy-3a,3b,6,6,9a-pentamethyl-2h,3h,9bh,10h,11h-cyclopenta[a]phenanthrene-4,7-dione)

INCHI for NP0299170 (1-(furan-3-yl)-3,5,10-trihydroxy-3a,3b,6,6,9a-pentamethyl-2h,3h,9bh,10h,11h-cyclopenta[a]phenanthrene-4,7-dione)

Structure for NP0299170 (1-(furan-3-yl)-3,5,10-trihydroxy-3a,3b,6,6,9a-pentamethyl-2h,3h,9bh,10h,11h-cyclopenta[a]phenanthrene-4,7-dione)

3D Structure for NP0299170 (1-(furan-3-yl)-3,5,10-trihydroxy-3a,3b,6,6,9a-pentamethyl-2h,3h,9bh,10h,11h-cyclopenta[a]phenanthrene-4,7-dione)