NP-MRD: Showing NP-Card for 2-{2,7-dihydroxy-3a,6,6,9a,11a-pentamethyl-1h,2h,3h,4h,5h,5ah,7h,8h,9h,10h,11h-cyclopenta[a]phenanthren-1-yl}-6-methyl-5-methylideneheptanoic acid (NP0331071)

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Record Information

Version

1.0

Created at

2022-09-12 17:03:25 UTC

Updated at

2022-09-12 17:03:25 UTC

NP-MRD ID

NP0331071

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2-{2,7-dihydroxy-3a,6,6,9a,11a-pentamethyl-1h,2h,3h,4h,5h,5ah,7h,8h,9h,10h,11h-cyclopenta[a]phenanthren-1-yl}-6-methyl-5-methylideneheptanoic acid

Description

2-{5,13-Dihydroxy-2,6,6,11,15-pentamethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadec-1(10)-en-14-yl}-6-methyl-5-methylideneheptanoic acid belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units. 2-{5,13-Dihydroxy-2,6,6,11,15-pentamethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadec-1(10)-en-14-yl}-6-methyl-5-methylideneheptanoic acid is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004201505392D          

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M  END

     RDKit          3D

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M  END


  Mrv1533004201505392D          

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    7.5104   -9.2798    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2950   -9.5347    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8973   -9.8318    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5474  -10.3397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5100  -10.5602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1127   -9.5769    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4996  -10.1289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7150   -9.8740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7668   -6.4899    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3543   -5.7754    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5918   -6.4899    0.0000 O   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
  4  5  2  0  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 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
  9 19  1  0  0  0  0
 13 19  1  0  0  0  0
 19 20  1  0  0  0  0
 16 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  1  0  0  0  0
 27 28  1  0  0  0  0
 27 29  1  0  0  0  0
 27 30  1  0  0  0  0
 21 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 15 32  1  0  0  0  0
  8 33  1  0  0  0  0
 33 34  2  0  0  0  0
 33 35  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0331071

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)C(=C)CCC(C1C(O)CC2(C)C3=C(CCC12C)C1(C)CCC(O)C(C)(C)C1CC3)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C31H50O4/c1-18(2)19(3)9-10-20(27(34)35)26-23(32)17-31(8)22-11-12-24-28(4,5)25(33)14-15-29(24,6)21(22)13-16-30(26,31)7/h18,20,23-26,32-33H,3,9-17H2,1-2,4-8H3,(H,34,35)

> <INCHI_KEY>
XADJANKGURNTIA-UHFFFAOYSA-N

> <FORMULA>
C31H50O4

> <MOLECULAR_WEIGHT>
486.737

> <EXACT_MASS>
486.37091009

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
85

> <JCHEM_AVERAGE_POLARIZABILITY>
57.732631832188375

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-{5,13-dihydroxy-2,6,6,11,15-pentamethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-1(10)-en-14-yl}-6-methyl-5-methylideneheptanoic acid

> <ALOGPS_LOGP>
5.39

> <JCHEM_LOGP>
5.678585907666669

> <ALOGPS_LOGS>
-4.94

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
14.901633417331983

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.773537913062996

> <JCHEM_PKA_STRONGEST_BASIC>
-0.8069747832914828

> <JCHEM_POLAR_SURFACE_AREA>
77.76

> <JCHEM_REFRACTIVITY>
141.30460000000005

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
5.61e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-{5,13-dihydroxy-2,6,6,11,15-pentamethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-1(10)-en-14-yl}-6-methyl-5-methylideneheptanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 20-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-APR-15         0                                  
HETATM    1  C   UNK     0      -1.765 -10.781   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.225 -10.781   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.545  -9.447   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.545 -12.114   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.225 -13.448   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.085 -12.114   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.855 -13.448   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.395 -13.448   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.165 -14.782   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.538 -16.189   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       3.032 -16.509   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       5.683 -17.219   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.016 -16.449   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.177 -17.981   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.481 -16.925   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       9.626 -15.895   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       9.305 -14.388   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       7.841 -13.912   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.696 -14.943   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.220 -13.478   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      11.090 -16.370   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      10.770 -14.864   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      12.235 -15.340   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      13.699 -15.816   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      14.019 -17.322   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      15.484 -17.798   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      12.875 -18.353   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      14.089 -19.301   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      12.152 -19.712   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      11.410 -17.877   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      10.266 -18.907   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       8.801 -18.431   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       5.165 -12.114   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       4.395 -10.781   0.000  0.00  0.00           O+0
HETATM   35  O   UNK     0       6.705 -12.114   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   33                                                  
CONECT    9    8   10   19                                                  
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12   14   15   19                                             
CONECT   14   13                                                            
CONECT   15   13   16   32                                                  
CONECT   16   15   17   21                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18    9   13   20                                             
CONECT   20   19                                                            
CONECT   21   16   22   23   30                                             
CONECT   22   21                                                            
CONECT   23   21   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28   29   30                                             
CONECT   28   27                                                            
CONECT   29   27                                                            
CONECT   30   27   21   31                                                  
CONECT   31   30   32                                                       
CONECT   32   31   15                                                       
CONECT   33    8   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33                                                            
MASTER        0    0    0    0    0    0    0    0   35    0   76    0
END

View in JSmol

Synonyms

Value	Source
2-{5,13-dihydroxy-2,6,6,11,15-pentamethyltetracyclo[8.7.0.0,.0,]heptadec-1(10)-en-14-yl}-6-methyl-5-methylideneheptanoate	Generator
2-{5,13-dihydroxy-2,6,6,11,15-pentamethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-1(10)-en-14-yl}-6-methyl-5-methylideneheptanoate	Generator

Chemical Formula

C₃₁H₅₀O₄

Average Mass

486.7370 Da

Monoisotopic Mass

486.37091 Da

IUPAC Name

2-{5,13-dihydroxy-2,6,6,11,15-pentamethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-1(10)-en-14-yl}-6-methyl-5-methylideneheptanoic acid

Traditional Name

2-{5,13-dihydroxy-2,6,6,11,15-pentamethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-1(10)-en-14-yl}-6-methyl-5-methylideneheptanoic acid

CAS Registry Number

Not Available

SMILES

CC(C)C(=C)CCC(C1C(O)CC2(C)C3=C(CCC12C)C1(C)CCC(O)C(C)(C)C1CC3)C(O)=O

InChI Identifier

InChI=1S/C31H50O4/c1-18(2)19(3)9-10-20(27(34)35)26-23(32)17-31(8)22-11-12-24-28(4,5)25(33)14-15-29(24,6)21(22)13-16-30(26,31)7/h18,20,23-26,32-33H,3,9-17H2,1-2,4-8H3,(H,34,35)

InChI Key

XADJANKGURNTIA-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

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
Dihydroxy bile acid, alcohol, or derivatives
Hydroxy bile acid, alcohol, or derivatives
Bile acid, alcohol, or derivatives
Steroid acid
3-hydroxysteroid
16-hydroxysteroid
Hydroxysteroid
Steroid
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
Alcohol
Organic oxygen compound
Carbonyl group
Organic oxide
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	5.39	ALOGPS
logP	5.68	ChemAxon
logS	-4.9	ALOGPS
pKa (Strongest Acidic)	4.77	ChemAxon
pKa (Strongest Basic)	-0.81	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	77.76 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	141.3 m³·mol⁻¹	ChemAxon
Polarizability	57.73 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	Yes	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

12314445

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 2-{2,7-dihydroxy-3a,6,6,9a,11a-pentamethyl-1h,2h,3h,4h,5h,5ah,7h,8h,9h,10h,11h-cyclopenta[a]phenanthren-1-yl}-6-methyl-5-methylideneheptanoic acid (NP0331071)

MOL for NP0331071 (2-{2,7-dihydroxy-3a,6,6,9a,11a-pentamethyl-1h,2h,3h,4h,5h,5ah,7h,8h,9h,10h,11h-cyclopenta[a]phenanthren-1-yl}-6-methyl-5-methylideneheptanoic acid)

3D MOL for NP0331071 (2-{2,7-dihydroxy-3a,6,6,9a,11a-pentamethyl-1h,2h,3h,4h,5h,5ah,7h,8h,9h,10h,11h-cyclopenta[a]phenanthren-1-yl}-6-methyl-5-methylideneheptanoic acid)

3D SDF for NP0331071 (2-{2,7-dihydroxy-3a,6,6,9a,11a-pentamethyl-1h,2h,3h,4h,5h,5ah,7h,8h,9h,10h,11h-cyclopenta[a]phenanthren-1-yl}-6-methyl-5-methylideneheptanoic acid)

3D-SDF for NP0331071 (2-{2,7-dihydroxy-3a,6,6,9a,11a-pentamethyl-1h,2h,3h,4h,5h,5ah,7h,8h,9h,10h,11h-cyclopenta[a]phenanthren-1-yl}-6-methyl-5-methylideneheptanoic acid)

PDB for NP0331071 (2-{2,7-dihydroxy-3a,6,6,9a,11a-pentamethyl-1h,2h,3h,4h,5h,5ah,7h,8h,9h,10h,11h-cyclopenta[a]phenanthren-1-yl}-6-methyl-5-methylideneheptanoic acid)

3D PDB for NP0331071 (2-{2,7-dihydroxy-3a,6,6,9a,11a-pentamethyl-1h,2h,3h,4h,5h,5ah,7h,8h,9h,10h,11h-cyclopenta[a]phenanthren-1-yl}-6-methyl-5-methylideneheptanoic acid)

SMILES for NP0331071 (2-{2,7-dihydroxy-3a,6,6,9a,11a-pentamethyl-1h,2h,3h,4h,5h,5ah,7h,8h,9h,10h,11h-cyclopenta[a]phenanthren-1-yl}-6-methyl-5-methylideneheptanoic acid)

INCHI for NP0331071 (2-{2,7-dihydroxy-3a,6,6,9a,11a-pentamethyl-1h,2h,3h,4h,5h,5ah,7h,8h,9h,10h,11h-cyclopenta[a]phenanthren-1-yl}-6-methyl-5-methylideneheptanoic acid)

Structure for NP0331071 (2-{2,7-dihydroxy-3a,6,6,9a,11a-pentamethyl-1h,2h,3h,4h,5h,5ah,7h,8h,9h,10h,11h-cyclopenta[a]phenanthren-1-yl}-6-methyl-5-methylideneheptanoic acid)

3D Structure for NP0331071 (2-{2,7-dihydroxy-3a,6,6,9a,11a-pentamethyl-1h,2h,3h,4h,5h,5ah,7h,8h,9h,10h,11h-cyclopenta[a]phenanthren-1-yl}-6-methyl-5-methylideneheptanoic acid)