NP-MRD: Showing NP-Card for 1-(7-hydroxy-5,6-dimethylheptan-2-yl)-9a,11a-dimethyl-tetradecahydrocyclopenta[a]phenanthrene-3,3b,5,6,7-pentol (NP0209508)

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Record Information

Version

2.0

Created at

2022-09-05 06:56:50 UTC

Updated at

2022-09-05 06:56:50 UTC

NP-MRD ID

NP0209508

Secondary Accession Numbers

None

Natural Product Identification

Common Name

1-(7-hydroxy-5,6-dimethylheptan-2-yl)-9a,11a-dimethyl-tetradecahydrocyclopenta[a]phenanthrene-3,3b,5,6,7-pentol

Description

14-(7-Hydroxy-5,6-dimethylheptan-2-yl)-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadecane-5,6,8,10,12-pentol belongs to the class of organic compounds known as pentahydroxy bile acids, alcohols and derivatives. These are bile acids, alcohols or derivatives bearing five hydroxyl groups. 1-(7-hydroxy-5,6-dimethylheptan-2-yl)-9a,11a-dimethyl-tetradecahydrocyclopenta[a]phenanthrene-3,3b,5,6,7-pentol is found in Certonardoa semiregularis. 14-(7-Hydroxy-5,6-dimethylheptan-2-yl)-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadecane-5,6,8,10,12-pentol is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004231521042D          

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M  END

     RDKit          3D

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M  END


  Mrv1533004231521042D          

 34 37  0  0  0  0            999 V2000
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    7.8457   -7.1069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3978   -7.7200    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0388   -7.2785    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7838   -8.0631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3358   -8.6762    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9768   -8.2346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4248   -7.6215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1699   -8.4061    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
  3  4  1  0  0  0  0
  2  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5  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
  9 11  1  0  0  0  0
 11 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  1  0  0  0  0
 11 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 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
 21 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 30 32  1  0  0  0  0
 32 33  1  0  0  0  0
 15 33  1  0  0  0  0
 20 33  1  0  0  0  0
 33 34  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0209508

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(CO)C(C)CCC(C)C1CC(O)C2C1(C)CCC1C3(C)CCC(O)C(O)C3C(O)CC21O

> <INCHI_IDENTIFIER>
InChI=1S/C28H50O6/c1-15(17(3)14-29)6-7-16(2)18-12-20(31)25-26(18,4)11-9-22-27(5)10-8-19(30)24(33)23(27)21(32)13-28(22,25)34/h15-25,29-34H,6-14H2,1-5H3

> <INCHI_KEY>
QLEHTNPUVWZOQF-UHFFFAOYSA-N

> <FORMULA>
C28H50O6

> <MOLECULAR_WEIGHT>
482.702

> <EXACT_MASS>
482.36073933

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
84

> <JCHEM_AVERAGE_POLARIZABILITY>
56.506592924431324

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
14-(7-hydroxy-5,6-dimethylheptan-2-yl)-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecane-5,6,8,10,12-pentol

> <ALOGPS_LOGP>
2.02

> <JCHEM_LOGP>
1.5273954736666673

> <ALOGPS_LOGS>
-3.31

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.112396505764188

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.519217075286996

> <JCHEM_PKA_STRONGEST_BASIC>
-1.618594009839275

> <JCHEM_POLAR_SURFACE_AREA>
121.38000000000001

> <JCHEM_REFRACTIVITY>
132.07720000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.34e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
14-(7-hydroxy-5,6-dimethylheptan-2-yl)-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecane-5,6,8,10,12-pentol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 23-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-APR-15         0                                  
HETATM    1  C   UNK     0      -0.486 -11.719   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.486 -13.259   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.819 -14.029   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      -3.153 -13.259   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       0.848 -14.029   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.848 -15.569   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.182 -13.259   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.515 -14.029   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.849 -13.259   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.849 -11.719   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.183 -14.029   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.344 -15.560   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.850 -15.881   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       8.476 -17.288   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       8.620 -14.547   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       7.590 -13.403   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.445 -12.372   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.065 -11.938   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       9.572 -11.618   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      10.602 -12.762   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      12.109 -12.442   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      11.078 -11.298   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      12.584 -10.977   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      14.091 -10.657   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      15.121 -11.802   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      16.628 -11.481   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      14.645 -13.266   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      15.676 -14.411   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      13.139 -13.586   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      12.663 -15.051   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      13.694 -16.196   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      11.157 -15.371   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      10.126 -14.227   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       9.650 -15.691   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    5                                                  
CONECT    3    2    4                                                       
CONECT    4    3                                                            
CONECT    5    2    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   16                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16   33                                                  
CONECT   16   15   11   17   18                                             
CONECT   17   16                                                            
CONECT   18   16   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21   33                                                  
CONECT   21   20   22   23   29                                             
CONECT   22   21                                                            
CONECT   23   21   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   21   30                                                  
CONECT   30   29   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30   33                                                       
CONECT   33   32   15   20   34                                             
CONECT   34   33                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   74    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₈H₅₀O₆

Average Mass

482.7020 Da

Monoisotopic Mass

482.36074 Da

IUPAC Name

14-(7-hydroxy-5,6-dimethylheptan-2-yl)-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecane-5,6,8,10,12-pentol

Traditional Name

14-(7-hydroxy-5,6-dimethylheptan-2-yl)-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecane-5,6,8,10,12-pentol

CAS Registry Number

Not Available

SMILES

CC(CO)C(C)CCC(C)C1CC(O)C2C1(C)CCC1C3(C)CCC(O)C(O)C3C(O)CC21O

InChI Identifier

InChI=1S/C28H50O6/c1-15(17(3)14-29)6-7-16(2)18-12-20(31)25-26(18,4)11-9-22-27(5)10-8-19(30)24(33)23(27)21(32)13-28(22,25)34/h15-25,29-34H,6-14H2,1-5H3

InChI Key

QLEHTNPUVWZOQF-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
Certonardoa semiregularis	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pentahydroxy bile acids, alcohols and derivatives. These are bile acids, alcohols or derivatives bearing five hydroxyl groups.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Bile acids, alcohols and derivatives

Direct Parent

Pentahydroxy bile acids, alcohols and derivatives

Alternative Parents

Substituents

Pentahydroxy bile acid, alcohol, or derivatives
26-hydroxysteroid
3-hydroxysteroid
4-hydroxysteroid
6-hydroxysteroid
15-hydroxysteroid
Hydroxysteroid
Fatty alcohol
Fatty acyl
Tertiary alcohol
Cyclic alcohol
Secondary alcohol
Polyol
Organooxygen compound
Primary alcohol
Hydrocarbon derivative
Organic oxygen compound
Alcohol
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	2.02	ALOGPS
logP	1.53	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Acidic)	13.52	ChemAxon
pKa (Strongest Basic)	-1.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	121.38 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	132.08 m³·mol⁻¹	ChemAxon
Polarizability	56.51 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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 1-(7-hydroxy-5,6-dimethylheptan-2-yl)-9a,11a-dimethyl-tetradecahydrocyclopenta[a]phenanthrene-3,3b,5,6,7-pentol (NP0209508)

MOL for NP0209508 (1-(7-hydroxy-5,6-dimethylheptan-2-yl)-9a,11a-dimethyl-tetradecahydrocyclopenta[a]phenanthrene-3,3b,5,6,7-pentol)

3D MOL for NP0209508 (1-(7-hydroxy-5,6-dimethylheptan-2-yl)-9a,11a-dimethyl-tetradecahydrocyclopenta[a]phenanthrene-3,3b,5,6,7-pentol)

3D SDF for NP0209508 (1-(7-hydroxy-5,6-dimethylheptan-2-yl)-9a,11a-dimethyl-tetradecahydrocyclopenta[a]phenanthrene-3,3b,5,6,7-pentol)

3D-SDF for NP0209508 (1-(7-hydroxy-5,6-dimethylheptan-2-yl)-9a,11a-dimethyl-tetradecahydrocyclopenta[a]phenanthrene-3,3b,5,6,7-pentol)

PDB for NP0209508 (1-(7-hydroxy-5,6-dimethylheptan-2-yl)-9a,11a-dimethyl-tetradecahydrocyclopenta[a]phenanthrene-3,3b,5,6,7-pentol)

3D PDB for NP0209508 (1-(7-hydroxy-5,6-dimethylheptan-2-yl)-9a,11a-dimethyl-tetradecahydrocyclopenta[a]phenanthrene-3,3b,5,6,7-pentol)

SMILES for NP0209508 (1-(7-hydroxy-5,6-dimethylheptan-2-yl)-9a,11a-dimethyl-tetradecahydrocyclopenta[a]phenanthrene-3,3b,5,6,7-pentol)

INCHI for NP0209508 (1-(7-hydroxy-5,6-dimethylheptan-2-yl)-9a,11a-dimethyl-tetradecahydrocyclopenta[a]phenanthrene-3,3b,5,6,7-pentol)

Structure for NP0209508 (1-(7-hydroxy-5,6-dimethylheptan-2-yl)-9a,11a-dimethyl-tetradecahydrocyclopenta[a]phenanthrene-3,3b,5,6,7-pentol)

3D Structure for NP0209508 (1-(7-hydroxy-5,6-dimethylheptan-2-yl)-9a,11a-dimethyl-tetradecahydrocyclopenta[a]phenanthrene-3,3b,5,6,7-pentol)