NP-MRD: Showing NP-Card for 4-{3-hydroxy-3a,6,6,9a,11a-pentamethyl-7-oxo-1h,2h,3h,5h,5ah,8h,9h,11h-cyclopenta[a]phenanthren-1-yl}pentanoic acid (NP0284395)

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Record Information

Version

2.0

Created at

2022-09-09 12:04:14 UTC

Updated at

2022-09-09 12:04:14 UTC

NP-MRD ID

NP0284395

Secondary Accession Numbers

None

Natural Product Identification

Common Name

4-{3-hydroxy-3a,6,6,9a,11a-pentamethyl-7-oxo-1h,2h,3h,5h,5ah,8h,9h,11h-cyclopenta[a]phenanthren-1-yl}pentanoic acid

Description

4-{12-Hydroxy-2,6,6,11,15-pentamethyl-5-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadeca-1(17),9-dien-14-yl}pentanoic acid belongs to the class of organic compounds known as monohydroxy bile acids, alcohols and derivatives. These are bile acids, alcohols or any of their derivatives bearing a hydroxyl group. 4-{3-hydroxy-3a,6,6,9a,11a-pentamethyl-7-oxo-1h,2h,3h,5h,5ah,8h,9h,11h-cyclopenta[a]phenanthren-1-yl}pentanoic acid is found in Ganoderma sinense. Based on a literature review very few articles have been published on 4-{12-hydroxy-2,6,6,11,15-pentamethyl-5-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadeca-1(17),9-dien-14-yl}pentanoic acid.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309092214042D          

 31 34  0  0  0  0            999 V2000
    2.8728   -3.9050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5619   -3.1408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7447   -3.0280    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2383   -3.6793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4211   -3.5665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0853   -4.2178    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1102   -2.8023    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0683   -2.4895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8390   -1.6970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5218   -1.2340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5486   -0.4095    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1731   -1.7404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3708   -0.9394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9853   -1.5952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2655   -0.8192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0777   -0.6740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    8.7655   -1.6450    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6731   -2.5662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8610   -2.7114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.5330   -3.2587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
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  3  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
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  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
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 29 30  1  0  0  0  0
  8 30  1  0  0  0  0
 12 30  1  0  0  0  0
 30 31  1  0  0  0  0
M  END

     RDKit          3D

 71 74  0  0  0  0  0  0  0  0999 V2000
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   -3.8581    2.0782   -0.6448 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1652309092214042D          

 31 34  0  0  0  0            999 V2000
    2.8728   -3.9050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END
> <DATABASE_ID>
NP0284395

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(CCC(O)=O)C1CC(O)C2(C)C3=CCC4C(C)(C)C(=O)CCC4(C)C3=CCC12C

> <INCHI_IDENTIFIER>
InChI=1S/C27H40O4/c1-16(7-10-23(30)31)19-15-22(29)27(6)18-8-9-20-24(2,3)21(28)12-13-25(20,4)17(18)11-14-26(19,27)5/h8,11,16,19-20,22,29H,7,9-10,12-15H2,1-6H3,(H,30,31)

> <INCHI_KEY>
PWADAHTZZKLCAK-UHFFFAOYSA-N

> <FORMULA>
C27H40O4

> <MOLECULAR_WEIGHT>
428.613

> <EXACT_MASS>
428.292659768

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
71

> <JCHEM_AVERAGE_POLARIZABILITY>
49.544989483590406

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
4-{12-hydroxy-2,6,6,11,15-pentamethyl-5-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-1(17),9-dien-14-yl}pentanoic acid

> <JCHEM_LOGP>
4.586648793

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
19.63517857538889

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.6241547947998205

> <JCHEM_PKA_STRONGEST_BASIC>
-0.43533866349327666

> <JCHEM_POLAR_SURFACE_AREA>
74.6

> <JCHEM_REFRACTIVITY>
123.41929999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
4-{12-hydroxy-2,6,6,11,15-pentamethyl-5-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-1(17),9-dien-14-yl}pentanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 09-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   09-SEP-22         0                                  
HETATM    1  C   UNK     0       5.363  -7.289   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.782  -5.863   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.257  -5.652   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.312  -6.868   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.786  -6.657   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      -0.159  -7.873   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0       0.206  -5.231   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       5.727  -4.647   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.299  -3.168   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.574  -2.304   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       6.624  -0.764   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       7.790  -3.249   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.159  -1.754   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.306  -2.978   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       9.829  -1.529   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      11.345  -1.258   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      12.338  -2.436   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      13.854  -2.164   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      13.323  -0.719   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      15.185  -1.391   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      14.846  -3.342   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      16.362  -3.071   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      14.323  -4.790   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      12.807  -5.061   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      11.814  -3.884   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      11.291  -5.332   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      10.299  -4.155   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       9.775  -5.603   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       8.259  -5.874   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       7.267  -4.697   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       6.595  -6.083   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    8                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5                                                            
CONECT    8    2    9   30                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13   14   30                                             
CONECT   13   12                                                            
CONECT   14   12   15   27                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   25                                                  
CONECT   18   17   19   20   21                                             
CONECT   19   18                                                            
CONECT   20   18                                                            
CONECT   21   18   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   17   26   27                                             
CONECT   26   25                                                            
CONECT   27   25   14   28                                                  
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29    8   12   31                                             
CONECT   31   30                                                            
MASTER        0    0    0    0    0    0    0    0   31    0   68    0
END

View in JSmol

Synonyms

Value	Source
4-{12-hydroxy-2,6,6,11,15-pentamethyl-5-oxotetracyclo[8.7.0.0,.0,]heptadeca-1(17),9-dien-14-yl}pentanoate	Generator

Chemical Formula

C₂₇H₄₀O₄

Average Mass

428.6130 Da

Monoisotopic Mass

428.29266 Da

IUPAC Name

4-{12-hydroxy-2,6,6,11,15-pentamethyl-5-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-1(17),9-dien-14-yl}pentanoic acid

Traditional Name

4-{12-hydroxy-2,6,6,11,15-pentamethyl-5-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-1(17),9-dien-14-yl}pentanoic acid

CAS Registry Number

Not Available

SMILES

CC(CCC(O)=O)C1CC(O)C2(C)C3=CCC4C(C)(C)C(=O)CCC4(C)C3=CCC12C

InChI Identifier

InChI=1S/C27H40O4/c1-16(7-10-23(30)31)19-15-22(29)27(6)18-8-9-20-24(2,3)21(28)12-13-25(20,4)17(18)11-14-26(19,27)5/h8,11,16,19-20,22,29H,7,9-10,12-15H2,1-6H3,(H,30,31)

InChI Key

PWADAHTZZKLCAK-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
Ganoderma sinense	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as monohydroxy bile acids, alcohols and derivatives. These are bile acids, alcohols or any of their derivatives bearing a hydroxyl group.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Bile acids, alcohols and derivatives

Direct Parent

Monohydroxy bile acids, alcohols and derivatives

Alternative Parents

Substituents

Monohydroxy bile acid, alcohol, or derivatives
3-oxo-delta-7-steroid
3-oxosteroid
15-hydroxysteroid
Hydroxysteroid
Oxosteroid
Delta-7-steroid
Cyclic alcohol
Ketone
Secondary alcohol
Cyclic ketone
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organooxygen compound
Organic oxygen compound
Alcohol
Carbonyl group
Hydrocarbon derivative
Organic oxide
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	4.59	ChemAxon
pKa (Strongest Acidic)	4.62	ChemAxon
pKa (Strongest Basic)	-0.44	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	74.6 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	123.42 m³·mol⁻¹	ChemAxon
Polarizability	49.54 Å³	ChemAxon
Number of Rings	4	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

162951632

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 4-{3-hydroxy-3a,6,6,9a,11a-pentamethyl-7-oxo-1h,2h,3h,5h,5ah,8h,9h,11h-cyclopenta[a]phenanthren-1-yl}pentanoic acid (NP0284395)

MOL for NP0284395 (4-{3-hydroxy-3a,6,6,9a,11a-pentamethyl-7-oxo-1h,2h,3h,5h,5ah,8h,9h,11h-cyclopenta[a]phenanthren-1-yl}pentanoic acid)

3D MOL for NP0284395 (4-{3-hydroxy-3a,6,6,9a,11a-pentamethyl-7-oxo-1h,2h,3h,5h,5ah,8h,9h,11h-cyclopenta[a]phenanthren-1-yl}pentanoic acid)

3D SDF for NP0284395 (4-{3-hydroxy-3a,6,6,9a,11a-pentamethyl-7-oxo-1h,2h,3h,5h,5ah,8h,9h,11h-cyclopenta[a]phenanthren-1-yl}pentanoic acid)

3D-SDF for NP0284395 (4-{3-hydroxy-3a,6,6,9a,11a-pentamethyl-7-oxo-1h,2h,3h,5h,5ah,8h,9h,11h-cyclopenta[a]phenanthren-1-yl}pentanoic acid)

PDB for NP0284395 (4-{3-hydroxy-3a,6,6,9a,11a-pentamethyl-7-oxo-1h,2h,3h,5h,5ah,8h,9h,11h-cyclopenta[a]phenanthren-1-yl}pentanoic acid)

3D PDB for NP0284395 (4-{3-hydroxy-3a,6,6,9a,11a-pentamethyl-7-oxo-1h,2h,3h,5h,5ah,8h,9h,11h-cyclopenta[a]phenanthren-1-yl}pentanoic acid)

SMILES for NP0284395 (4-{3-hydroxy-3a,6,6,9a,11a-pentamethyl-7-oxo-1h,2h,3h,5h,5ah,8h,9h,11h-cyclopenta[a]phenanthren-1-yl}pentanoic acid)

INCHI for NP0284395 (4-{3-hydroxy-3a,6,6,9a,11a-pentamethyl-7-oxo-1h,2h,3h,5h,5ah,8h,9h,11h-cyclopenta[a]phenanthren-1-yl}pentanoic acid)

Structure for NP0284395 (4-{3-hydroxy-3a,6,6,9a,11a-pentamethyl-7-oxo-1h,2h,3h,5h,5ah,8h,9h,11h-cyclopenta[a]phenanthren-1-yl}pentanoic acid)

3D Structure for NP0284395 (4-{3-hydroxy-3a,6,6,9a,11a-pentamethyl-7-oxo-1h,2h,3h,5h,5ah,8h,9h,11h-cyclopenta[a]phenanthren-1-yl}pentanoic acid)