NP-MRD: Showing NP-Card for (4r)-4-[(1r,3ar,5ar,9as,11ar)-3a,6,6,9a,11a-pentamethyl-2,4,7,10,11-pentaoxo-1h,3h,5h,5ah,8h,9h-cyclopenta[a]phenanthren-1-yl]pentanoic acid (NP0215221)

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Record Information

Version

2.0

Created at

2022-09-05 14:45:44 UTC

Updated at

2022-09-05 14:45:44 UTC

NP-MRD ID

NP0215221

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(4r)-4-[(1r,3ar,5ar,9as,11ar)-3a,6,6,9a,11a-pentamethyl-2,4,7,10,11-pentaoxo-1h,3h,5h,5ah,8h,9h-cyclopenta[a]phenanthren-1-yl]pentanoic acid

Description

(4R)-4-[(2S,7R,11R,14R,15R)-2,6,6,11,15-pentamethyl-5,9,13,16,17-pentaoxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadec-1(10)-en-14-yl]pentanoic acid belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units. Based on a literature review very few articles have been published on (4R)-4-[(2S,7R,11R,14R,15R)-2,6,6,11,15-pentamethyl-5,9,13,16,17-pentaoxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadec-1(10)-en-14-yl]pentanoic acid.

Structure

MOL 3D MOL SDF PDB SMILES InChI

  Mrv1652309052216452D          

 34 37  0  0  1  0            999 V2000
    4.9830   -1.5571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

     RDKit          3D

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M  END

  Mrv1652309052216452D          

 34 37  0  0  1  0            999 V2000
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M  END
> <DATABASE_ID>
NP0215221

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@H](CCC(O)=O)[C@H]1C(=O)C[C@@]2(C)C3=C(C(=O)C(=O)[C@]12C)[C@@]1(C)CCC(=O)C(C)(C)[C@@H]1CC3=O

> <INCHI_IDENTIFIER>
InChI=1S/C27H34O7/c1-13(7-8-18(31)32)19-15(29)12-26(5)20-14(28)11-16-24(2,3)17(30)9-10-25(16,4)21(20)22(33)23(34)27(19,26)6/h13,16,19H,7-12H2,1-6H3,(H,31,32)/t13-,16+,19+,25+,26+,27+/m1/s1

> <INCHI_KEY>
SEOWBYMXTMBDQO-XFLVOATNSA-N

> <FORMULA>
C27H34O7

> <MOLECULAR_WEIGHT>
470.562

> <EXACT_MASS>
470.230453435

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
68

> <JCHEM_AVERAGE_POLARIZABILITY>
50.13728486762333

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(4R)-4-[(2S,7R,11R,14R,15R)-2,6,6,11,15-pentamethyl-5,9,13,16,17-pentaoxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-1(10)-en-14-yl]pentanoic acid

> <JCHEM_LOGP>
4.278149617333335

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
18.07727198812138

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.02410733310016

> <JCHEM_PKA_STRONGEST_BASIC>
-7.076853683794323

> <JCHEM_POLAR_SURFACE_AREA>
122.65

> <JCHEM_REFRACTIVITY>
123.6376999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(4R)-4-[(2S,7R,11R,14R,15R)-2,6,6,11,15-pentamethyl-5,9,13,16,17-pentaoxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-1(10)-en-14-yl]pentanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 05-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-SEP-22         0                                  
HETATM    1  C   UNK     0       9.302  -2.907   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.882  -1.480   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      11.407  -1.269   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      12.353  -2.485   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      13.878  -2.275   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      14.823  -3.490   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0      14.458  -0.848   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       8.937  -0.264   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.365   1.215   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      10.813   1.738   0.000  0.00  0.00           O+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       6.505   2.629   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.358   1.405   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.366   0.228   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.889  -1.221   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       3.896  -2.398   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       6.405  -1.492   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       6.928  -2.940   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       7.398  -0.314   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       8.069  -1.700   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       2.850   0.499   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       3.373  -0.949   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       1.857  -0.678   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       0.341  -0.407   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -0.182   1.041   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      -1.698   1.312   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       0.810   2.218   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -0.521   2.992   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       1.341   3.664   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       2.326   1.947   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       3.319   3.125   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       4.835   2.854   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       5.828   4.031   0.000  0.00  0.00           O+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   20                                                  
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11   13   14   20                                             
CONECT   13   12                                                            
CONECT   14   12   15   33                                                  
CONECT   15   14   16   22                                                  
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18    8   12   21                                             
CONECT   21   20                                                            
CONECT   22   15   23   24   31                                             
CONECT   23   22                                                            
CONECT   24   22   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   29   30   31                                             
CONECT   29   28                                                            
CONECT   30   28                                                            
CONECT   31   28   22   32                                                  
CONECT   32   31   33                                                       
CONECT   33   32   14   34                                                  
CONECT   34   33                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   74    0
END

View in JSmol

Synonyms

Value	Source
(4R)-4-[(2S,7R,11R,14R,15R)-2,6,6,11,15-Pentamethyl-5,9,13,16,17-pentaoxotetracyclo[8.7.0.0,.0,]heptadec-1(10)-en-14-yl]pentanoate	Generator

Chemical Formula

C₂₇H₃₄O₇

Average Mass

470.5620 Da

Monoisotopic Mass

470.23045 Da

IUPAC Name

(4R)-4-[(2S,7R,11R,14R,15R)-2,6,6,11,15-pentamethyl-5,9,13,16,17-pentaoxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-1(10)-en-14-yl]pentanoic acid

Traditional Name

(4R)-4-[(2S,7R,11R,14R,15R)-2,6,6,11,15-pentamethyl-5,9,13,16,17-pentaoxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-1(10)-en-14-yl]pentanoic acid

CAS Registry Number

Not Available

SMILES

C[C@H](CCC(O)=O)[C@H]1C(=O)C[C@@]2(C)C3=C(C(=O)C(=O)[C@]12C)[C@@]1(C)CCC(=O)C(C)(C)[C@@H]1CC3=O

InChI Identifier

InChI=1S/C27H34O7/c1-13(7-8-18(31)32)19-15(29)12-26(5)20-14(28)11-16-24(2,3)17(30)9-10-25(16,4)21(20)22(33)23(34)27(19,26)6/h13,16,19H,7-12H2,1-6H3,(H,31,32)/t13-,16+,19+,25+,26+,27+/m1/s1

InChI Key

SEOWBYMXTMBDQO-XFLVOATNSA-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

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Triterpenoids

Direct Parent

Triterpenoids

Alternative Parents

Substituents

Triterpenoid
Bile acid, alcohol, or derivatives
3-oxosteroid
11-oxosteroid
16-oxosteroid
12-oxosteroid
Oxosteroid
7-oxosteroid
3-oxo-5-alpha-steroid
14-alpha-methylsteroid
Steroid
Cyclohexenone
Ketone
Cyclic ketone
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Carbonyl group
Organic oxygen compound
Organooxygen compound
Organic oxide
Hydrocarbon derivative
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	4.28	ChemAxon
pKa (Strongest Acidic)	4.02	ChemAxon
pKa (Strongest Basic)	-7.1	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	122.65 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	123.64 m³·mol⁻¹	ChemAxon
Polarizability	50.14 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

78437256

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

139585468

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (4r)-4-[(1r,3ar,5ar,9as,11ar)-3a,6,6,9a,11a-pentamethyl-2,4,7,10,11-pentaoxo-1h,3h,5h,5ah,8h,9h-cyclopenta[a]phenanthren-1-yl]pentanoic acid (NP0215221)

MOL for NP0215221 ((4r)-4-[(1r,3ar,5ar,9as,11ar)-3a,6,6,9a,11a-pentamethyl-2,4,7,10,11-pentaoxo-1h,3h,5h,5ah,8h,9h-cyclopenta[a]phenanthren-1-yl]pentanoic acid)

3D MOL for NP0215221 ((4r)-4-[(1r,3ar,5ar,9as,11ar)-3a,6,6,9a,11a-pentamethyl-2,4,7,10,11-pentaoxo-1h,3h,5h,5ah,8h,9h-cyclopenta[a]phenanthren-1-yl]pentanoic acid)

3D SDF for NP0215221 ((4r)-4-[(1r,3ar,5ar,9as,11ar)-3a,6,6,9a,11a-pentamethyl-2,4,7,10,11-pentaoxo-1h,3h,5h,5ah,8h,9h-cyclopenta[a]phenanthren-1-yl]pentanoic acid)

3D-SDF for NP0215221 ((4r)-4-[(1r,3ar,5ar,9as,11ar)-3a,6,6,9a,11a-pentamethyl-2,4,7,10,11-pentaoxo-1h,3h,5h,5ah,8h,9h-cyclopenta[a]phenanthren-1-yl]pentanoic acid)

PDB for NP0215221 ((4r)-4-[(1r,3ar,5ar,9as,11ar)-3a,6,6,9a,11a-pentamethyl-2,4,7,10,11-pentaoxo-1h,3h,5h,5ah,8h,9h-cyclopenta[a]phenanthren-1-yl]pentanoic acid)

3D PDB for NP0215221 ((4r)-4-[(1r,3ar,5ar,9as,11ar)-3a,6,6,9a,11a-pentamethyl-2,4,7,10,11-pentaoxo-1h,3h,5h,5ah,8h,9h-cyclopenta[a]phenanthren-1-yl]pentanoic acid)

SMILES for NP0215221 ((4r)-4-[(1r,3ar,5ar,9as,11ar)-3a,6,6,9a,11a-pentamethyl-2,4,7,10,11-pentaoxo-1h,3h,5h,5ah,8h,9h-cyclopenta[a]phenanthren-1-yl]pentanoic acid)

INCHI for NP0215221 ((4r)-4-[(1r,3ar,5ar,9as,11ar)-3a,6,6,9a,11a-pentamethyl-2,4,7,10,11-pentaoxo-1h,3h,5h,5ah,8h,9h-cyclopenta[a]phenanthren-1-yl]pentanoic acid)

Structure for NP0215221 ((4r)-4-[(1r,3ar,5ar,9as,11ar)-3a,6,6,9a,11a-pentamethyl-2,4,7,10,11-pentaoxo-1h,3h,5h,5ah,8h,9h-cyclopenta[a]phenanthren-1-yl]pentanoic acid)

3D Structure for NP0215221 ((4r)-4-[(1r,3ar,5ar,9as,11ar)-3a,6,6,9a,11a-pentamethyl-2,4,7,10,11-pentaoxo-1h,3h,5h,5ah,8h,9h-cyclopenta[a]phenanthren-1-yl]pentanoic acid)