NP-MRD: Showing NP-Card for (2e,6r)-6-[(1s,5ar,7r,9as,11as)-7-hydroxy-1,6,6,9a,11a-pentamethyl-2h,4h,5h,5ah,7h,8h,9h,10h,11h-cyclopenta[a]phenanthren-1-yl]-2-methylhept-2-enoic acid (NP0302454)

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Record Information

Version

2.0

Created at

2022-09-10 16:03:33 UTC

Updated at

2022-09-10 16:03:34 UTC

NP-MRD ID

NP0302454

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2e,6r)-6-[(1s,5ar,7r,9as,11as)-7-hydroxy-1,6,6,9a,11a-pentamethyl-2h,4h,5h,5ah,7h,8h,9h,10h,11h-cyclopenta[a]phenanthren-1-yl]-2-methylhept-2-enoic acid

Description

(13Alpha,17S,24E)-3alpha-Hydroxy-17-methyl-14-demethyl-5alpha-lanosta-8,14,24-triene-26-oic 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. (2e,6r)-6-[(1s,5ar,7r,9as,11as)-7-hydroxy-1,6,6,9a,11a-pentamethyl-2h,4h,5h,5ah,7h,8h,9h,10h,11h-cyclopenta[a]phenanthren-1-yl]-2-methylhept-2-enoic acid is found in Garcinia hombroniana. Based on a literature review very few articles have been published on (13alpha,17S,24E)-3alpha-Hydroxy-17-methyl-14-demethyl-5alpha-lanosta-8,14,24-triene-26-oic acid.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309102218032D          

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M  END

     RDKit          3D

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M  END


  Mrv1652309102218032D          

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  6  7  1  1  0  0  0
  8  6  1  1  0  0  0
  8  9  1  6  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 12 17  1  0  0  0  0
  8 17  1  0  0  0  0
 17 18  1  1  0  0  0
 14 19  1  0  0  0  0
 19 20  1  6  0  0  0
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  1  0  0  0
 23 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  1  0  0  0  0
 25 28  1  0  0  0  0
 19 28  1  0  0  0  0
 28 29  1  6  0  0  0
 29 30  1  0  0  0  0
 13 30  1  0  0  0  0
  2 31  1  0  0  0  0
 31 32  2  0  0  0  0
 31 33  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0302454

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@H](CC\C=C(/C)C(O)=O)[C@]1(C)CC=C2C3=C(CC[C@@]12C)[C@@]1(C)CC[C@@H](O)C(C)(C)[C@@H]1CC3

> <INCHI_IDENTIFIER>
InChI=1S/C30H46O3/c1-19(26(32)33)9-8-10-20(2)29(6)17-14-23-21-11-12-24-27(3,4)25(31)15-16-28(24,5)22(21)13-18-30(23,29)7/h9,14,20,24-25,31H,8,10-13,15-18H2,1-7H3,(H,32,33)/b19-9+/t20-,24+,25-,28-,29+,30-/m1/s1

> <INCHI_KEY>
GFTFIKIFKMPWNH-XUMMNONCSA-N

> <FORMULA>
C30H46O3

> <MOLECULAR_WEIGHT>
454.695

> <EXACT_MASS>
454.344695341

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
79

> <JCHEM_AVERAGE_POLARIZABILITY>
55.12930729627525

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2E,6R)-6-[(2S,5R,7R,14S,15S)-5-hydroxy-2,6,6,14,15-pentamethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-1(10),11-dien-14-yl]-2-methylhept-2-enoic acid

> <JCHEM_LOGP>
6.492785638666668

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
19.55378667739605

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.952208544641751

> <JCHEM_PKA_STRONGEST_BASIC>
-0.8069744634473587

> <JCHEM_POLAR_SURFACE_AREA>
57.53

> <JCHEM_REFRACTIVITY>
137.11190000000005

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(2E,6R)-6-[(2S,5R,7R,14S,15S)-5-hydroxy-2,6,6,14,15-pentamethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-1(10),11-dien-14-yl]-2-methylhept-2-enoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 10-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-SEP-22         0                                  
HETATM    1  C   UNK     0      15.993  -0.171   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      15.470   1.277   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      13.954   1.548   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      12.961   0.371   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      11.445   0.642   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      10.453  -0.535   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      10.976  -1.984   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.937  -0.264   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.826  -1.800   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.365   1.215   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.090   2.079   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.874   1.134   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.358   1.405   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.366   0.228   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.889  -1.221   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.405  -1.492   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       7.398  -0.314   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.069  -1.700   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.850   0.499   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       3.373  -0.949   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       1.857  -0.678   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       0.341  -0.407   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -0.182   1.041   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      -1.698   1.312   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       0.810   2.218   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -0.521   2.992   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       1.341   3.664   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       2.326   1.947   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       3.319   3.125   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       4.835   2.854   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      16.463   2.455   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      15.940   3.903   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0      17.979   2.183   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   31                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   10   17                                             
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   17                                                  
CONECT   13   12   14   30                                                  
CONECT   14   13   15   19                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   12    8   18                                             
CONECT   18   17                                                            
CONECT   19   14   20   21   28                                             
CONECT   20   19                                                            
CONECT   21   19   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26   27   28                                             
CONECT   26   25                                                            
CONECT   27   25                                                            
CONECT   28   25   19   29                                                  
CONECT   29   28   30                                                       
CONECT   30   29   13                                                       
CONECT   31    2   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   72    0
END

View in JSmol

Synonyms

Value	Source
(13a,17S,24E)-3a-Hydroxy-17-methyl-14-demethyl-5a-lanosta-8,14,24-triene-26-Oate	Generator
(13a,17S,24E)-3a-Hydroxy-17-methyl-14-demethyl-5a-lanosta-8,14,24-triene-26-Oic acid	Generator
(13alpha,17S,24E)-3alpha-Hydroxy-17-methyl-14-demethyl-5alpha-lanosta-8,14,24-triene-26-Oate	Generator
(13Α,17S,24E)-3α-hydroxy-17-methyl-14-demethyl-5α-lanosta-8,14,24-triene-26-Oate	Generator
(13Α,17S,24E)-3α-hydroxy-17-methyl-14-demethyl-5α-lanosta-8,14,24-triene-26-Oic acid	Generator

Chemical Formula

C₃₀H₄₆O₃

Average Mass

454.6950 Da

Monoisotopic Mass

454.34470 Da

IUPAC Name

(2E,6R)-6-[(2S,5R,7R,14S,15S)-5-hydroxy-2,6,6,14,15-pentamethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-1(10),11-dien-14-yl]-2-methylhept-2-enoic acid

Traditional Name

(2E,6R)-6-[(2S,5R,7R,14S,15S)-5-hydroxy-2,6,6,14,15-pentamethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-1(10),11-dien-14-yl]-2-methylhept-2-enoic acid

CAS Registry Number

Not Available

SMILES

C[C@H](CC\C=C(/C)C(O)=O)[C@]1(C)CC=C2C3=C(CC[C@@]12C)[C@@]1(C)CC[C@@H](O)C(C)(C)[C@@H]1CC3

InChI Identifier

InChI=1S/C30H46O3/c1-19(26(32)33)9-8-10-20(2)29(6)17-14-23-21-11-12-24-27(3,4)25(31)15-16-28(24,5)22(21)13-18-30(23,29)7/h9,14,20,24-25,31H,8,10-13,15-18H2,1-7H3,(H,32,33)/b19-9+/t20-,24+,25-,28-,29+,30-/m1/s1

InChI Key

GFTFIKIFKMPWNH-XUMMNONCSA-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
Garcinia hombroniana	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
Steroid acid
3-hydroxysteroid
3-alpha-hydroxysteroid
Hydroxysteroid
Medium-chain fatty acid
Hydroxy fatty acid
Fatty acyl
Fatty acid
Unsaturated fatty acid
Cyclic alcohol
Secondary alcohol
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Organic oxide
Alcohol
Organic oxygen compound
Carbonyl group
Hydrocarbon derivative
Organooxygen compound
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	6.49	ChemAxon
pKa (Strongest Acidic)	4.95	ChemAxon
pKa (Strongest Basic)	-0.81	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	57.53 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	137.11 m³·mol⁻¹	ChemAxon
Polarizability	55.13 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	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

15546292

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2e,6r)-6-[(1s,5ar,7r,9as,11as)-7-hydroxy-1,6,6,9a,11a-pentamethyl-2h,4h,5h,5ah,7h,8h,9h,10h,11h-cyclopenta[a]phenanthren-1-yl]-2-methylhept-2-enoic acid (NP0302454)

MOL for NP0302454 ((2e,6r)-6-[(1s,5ar,7r,9as,11as)-7-hydroxy-1,6,6,9a,11a-pentamethyl-2h,4h,5h,5ah,7h,8h,9h,10h,11h-cyclopenta[a]phenanthren-1-yl]-2-methylhept-2-enoic acid)

3D MOL for NP0302454 ((2e,6r)-6-[(1s,5ar,7r,9as,11as)-7-hydroxy-1,6,6,9a,11a-pentamethyl-2h,4h,5h,5ah,7h,8h,9h,10h,11h-cyclopenta[a]phenanthren-1-yl]-2-methylhept-2-enoic acid)

3D SDF for NP0302454 ((2e,6r)-6-[(1s,5ar,7r,9as,11as)-7-hydroxy-1,6,6,9a,11a-pentamethyl-2h,4h,5h,5ah,7h,8h,9h,10h,11h-cyclopenta[a]phenanthren-1-yl]-2-methylhept-2-enoic acid)

3D-SDF for NP0302454 ((2e,6r)-6-[(1s,5ar,7r,9as,11as)-7-hydroxy-1,6,6,9a,11a-pentamethyl-2h,4h,5h,5ah,7h,8h,9h,10h,11h-cyclopenta[a]phenanthren-1-yl]-2-methylhept-2-enoic acid)

PDB for NP0302454 ((2e,6r)-6-[(1s,5ar,7r,9as,11as)-7-hydroxy-1,6,6,9a,11a-pentamethyl-2h,4h,5h,5ah,7h,8h,9h,10h,11h-cyclopenta[a]phenanthren-1-yl]-2-methylhept-2-enoic acid)

3D PDB for NP0302454 ((2e,6r)-6-[(1s,5ar,7r,9as,11as)-7-hydroxy-1,6,6,9a,11a-pentamethyl-2h,4h,5h,5ah,7h,8h,9h,10h,11h-cyclopenta[a]phenanthren-1-yl]-2-methylhept-2-enoic acid)

SMILES for NP0302454 ((2e,6r)-6-[(1s,5ar,7r,9as,11as)-7-hydroxy-1,6,6,9a,11a-pentamethyl-2h,4h,5h,5ah,7h,8h,9h,10h,11h-cyclopenta[a]phenanthren-1-yl]-2-methylhept-2-enoic acid)

INCHI for NP0302454 ((2e,6r)-6-[(1s,5ar,7r,9as,11as)-7-hydroxy-1,6,6,9a,11a-pentamethyl-2h,4h,5h,5ah,7h,8h,9h,10h,11h-cyclopenta[a]phenanthren-1-yl]-2-methylhept-2-enoic acid)

Structure for NP0302454 ((2e,6r)-6-[(1s,5ar,7r,9as,11as)-7-hydroxy-1,6,6,9a,11a-pentamethyl-2h,4h,5h,5ah,7h,8h,9h,10h,11h-cyclopenta[a]phenanthren-1-yl]-2-methylhept-2-enoic acid)

3D Structure for NP0302454 ((2e,6r)-6-[(1s,5ar,7r,9as,11as)-7-hydroxy-1,6,6,9a,11a-pentamethyl-2h,4h,5h,5ah,7h,8h,9h,10h,11h-cyclopenta[a]phenanthren-1-yl]-2-methylhept-2-enoic acid)