NP-MRD: Showing NP-Card for 1-(6,7-dihydroxy-5-isopropyloctan-2-yl)-9a,11a-dimethyl-dodecahydro-1h-cyclopenta[a]phenanthrene-3,3b,5,5a,7-pentol (NP0209734)

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Record Information

Version

2.0

Created at

2022-09-05 07:15:51 UTC

Updated at

2022-09-05 07:15:51 UTC

NP-MRD ID

NP0209734

Secondary Accession Numbers

None

Natural Product Identification

Common Name

1-(6,7-dihydroxy-5-isopropyloctan-2-yl)-9a,11a-dimethyl-dodecahydro-1h-cyclopenta[a]phenanthrene-3,3b,5,5a,7-pentol

Description

14-[6,7-Dihydroxy-5-(propan-2-yl)octan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadecane-5,7,8,10,12-pentol belongs to the class of organic compounds known as stigmastanes and derivatives. These are sterol lipids with a structure based on the stigmastane skeleton, which consists of a cholestane moiety bearing an ethyl group at the carbon atom C24. 1-(6,7-dihydroxy-5-isopropyloctan-2-yl)-9a,11a-dimethyl-dodecahydro-1h-cyclopenta[a]phenanthrene-3,3b,5,5a,7-pentol is found in Ctenodiscus crispatus. 14-[6,7-Dihydroxy-5-(propan-2-yl)octan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadecane-5,7,8,10,12-pentol is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004161513352D          

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M  END

     RDKit          3D

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M  END


  Mrv1533004161513352D          

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   -2.7952   -5.1280    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9882   -4.9565    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2036   -4.7016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4362   -5.5696    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6911   -6.3542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4981   -6.5258    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7530   -7.3104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9460   -7.1389    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2010   -7.9235    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4559   -8.7081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2629   -8.8796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5178   -9.6642    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8149   -8.2665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5600   -7.4819    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3669   -7.6534    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1120   -6.8688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9190   -7.0403    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8571   -6.0842    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0501   -5.9127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6021   -5.2996    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6704   -3.7235    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6704   -2.8985    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3849   -4.1360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0993   -3.7235    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3849   -4.9610    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  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
  9 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  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
 19 20  1  0  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  0  0  0  0
 23 25  1  0  0  0  0
 25 26  1  0  0  0  0
 19 26  1  0  0  0  0
 26 27  1  0  0  0  0
 26 28  1  0  0  0  0
 28 29  1  0  0  0  0
 28 30  1  0  0  0  0
 30 31  1  0  0  0  0
 13 31  1  0  0  0  0
 18 31  1  0  0  0  0
 31 32  1  0  0  0  0
  4 33  1  0  0  0  0
 33 34  1  0  0  0  0
 33 35  1  0  0  0  0
 35 36  1  0  0  0  0
 35 37  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0209734

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)C(CCC(C)C1CC(O)C2C1(C)CCC1C2(O)CC(O)C2(O)CC(O)CCC12C)C(O)C(C)O

> <INCHI_IDENTIFIER>
InChI=1S/C30H54O7/c1-16(2)20(25(35)18(4)31)8-7-17(3)21-13-22(33)26-27(21,5)11-10-23-28(6)12-9-19(32)14-30(28,37)24(34)15-29(23,26)36/h16-26,31-37H,7-15H2,1-6H3

> <INCHI_KEY>
MDHQKLXMPNKCJH-UHFFFAOYSA-N

> <FORMULA>
C30H54O7

> <MOLECULAR_WEIGHT>
526.755

> <EXACT_MASS>
526.386954079

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
91

> <JCHEM_AVERAGE_POLARIZABILITY>
60.99191172342485

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
2.00

> <JCHEM_LOGP>
1.348749855333332

> <ALOGPS_LOGS>
-3.41

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.724058098441038

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.111841487858467

> <JCHEM_PKA_STRONGEST_BASIC>
-2.7280228885913527

> <JCHEM_POLAR_SURFACE_AREA>
141.61

> <JCHEM_REFRACTIVITY>
142.4493

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.04e-01 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 16-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   16-APR-15         0                                  
HETATM    1  C   UNK     0       3.118 -10.031   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.784  -9.261   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.451 -10.031   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.784  -7.721   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.451  -6.951   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.883  -7.721   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.217  -6.951   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.217  -5.411   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -3.550  -7.721   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -4.957  -7.094   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -5.988  -8.239   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -7.519  -8.078   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      -5.218  -9.572   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -3.711  -9.252   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -2.247  -8.776   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -2.681 -10.397   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -3.157 -11.861   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -4.663 -12.181   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -5.139 -13.646   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -3.633 -13.326   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -4.108 -14.790   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -4.584 -16.255   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -6.091 -16.575   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      -6.567 -18.040   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      -7.121 -15.431   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -6.645 -13.966   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      -8.152 -14.286   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      -7.676 -12.822   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      -9.182 -13.142   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      -7.200 -11.357   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -5.694 -11.037   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      -6.724  -9.893   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       3.118  -6.951   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       3.118  -5.411   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0       4.452  -7.721   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       5.785  -6.951   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0       4.452  -9.261   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5   33                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   14                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   31                                                  
CONECT   14   13    9   15   16                                             
CONECT   15   14                                                            
CONECT   16   14   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   31                                                  
CONECT   19   18   20   21   26                                             
CONECT   20   19                                                            
CONECT   21   19   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26                                                       
CONECT   26   25   19   27   28                                             
CONECT   27   26                                                            
CONECT   28   26   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   31                                                       
CONECT   31   30   13   18   32                                             
CONECT   32   31                                                            
CONECT   33    4   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33   36   37                                                  
CONECT   36   35                                                            
CONECT   37   35                                                            
MASTER        0    0    0    0    0    0    0    0   37    0   80    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₀H₅₄O₇

Average Mass

526.7550 Da

Monoisotopic Mass

526.38695 Da

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

CC(C)C(CCC(C)C1CC(O)C2C1(C)CCC1C2(O)CC(O)C2(O)CC(O)CCC12C)C(O)C(C)O

InChI Identifier

InChI=1S/C30H54O7/c1-16(2)20(25(35)18(4)31)8-7-17(3)21-13-22(33)26-27(21,5)11-10-23-28(6)12-9-19(32)14-30(28,37)24(34)15-29(23,26)36/h16-26,31-37H,7-15H2,1-6H3

InChI Key

MDHQKLXMPNKCJH-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
Ctenodiscus crispatus	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as stigmastanes and derivatives. These are sterol lipids with a structure based on the stigmastane skeleton, which consists of a cholestane moiety bearing an ethyl group at the carbon atom C24.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Stigmastanes and derivatives

Direct Parent

Stigmastanes and derivatives

Alternative Parents

Substituents

Stigmastane-skeleton
Triterpenoid
27-hydroxysteroid
25-hydroxysteroid
3-hydroxysteroid
6-hydroxysteroid
15-hydroxysteroid
5-hydroxysteroid
Hydroxysteroid
Fatty alcohol
Fatty acyl
Cyclic alcohol
Tertiary alcohol
Secondary alcohol
Polyol
Hydrocarbon derivative
Organic oxygen compound
Alcohol
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	2	ALOGPS
logP	1.35	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Acidic)	13.11	ChemAxon
pKa (Strongest Basic)	-2.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	141.61 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	142.45 m³·mol⁻¹	ChemAxon
Polarizability	60.99 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	No	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

73835784

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 1-(6,7-dihydroxy-5-isopropyloctan-2-yl)-9a,11a-dimethyl-dodecahydro-1h-cyclopenta[a]phenanthrene-3,3b,5,5a,7-pentol (NP0209734)

MOL for NP0209734 (1-(6,7-dihydroxy-5-isopropyloctan-2-yl)-9a,11a-dimethyl-dodecahydro-1h-cyclopenta[a]phenanthrene-3,3b,5,5a,7-pentol)

3D MOL for NP0209734 (1-(6,7-dihydroxy-5-isopropyloctan-2-yl)-9a,11a-dimethyl-dodecahydro-1h-cyclopenta[a]phenanthrene-3,3b,5,5a,7-pentol)

3D SDF for NP0209734 (1-(6,7-dihydroxy-5-isopropyloctan-2-yl)-9a,11a-dimethyl-dodecahydro-1h-cyclopenta[a]phenanthrene-3,3b,5,5a,7-pentol)

3D-SDF for NP0209734 (1-(6,7-dihydroxy-5-isopropyloctan-2-yl)-9a,11a-dimethyl-dodecahydro-1h-cyclopenta[a]phenanthrene-3,3b,5,5a,7-pentol)

PDB for NP0209734 (1-(6,7-dihydroxy-5-isopropyloctan-2-yl)-9a,11a-dimethyl-dodecahydro-1h-cyclopenta[a]phenanthrene-3,3b,5,5a,7-pentol)

3D PDB for NP0209734 (1-(6,7-dihydroxy-5-isopropyloctan-2-yl)-9a,11a-dimethyl-dodecahydro-1h-cyclopenta[a]phenanthrene-3,3b,5,5a,7-pentol)

SMILES for NP0209734 (1-(6,7-dihydroxy-5-isopropyloctan-2-yl)-9a,11a-dimethyl-dodecahydro-1h-cyclopenta[a]phenanthrene-3,3b,5,5a,7-pentol)

INCHI for NP0209734 (1-(6,7-dihydroxy-5-isopropyloctan-2-yl)-9a,11a-dimethyl-dodecahydro-1h-cyclopenta[a]phenanthrene-3,3b,5,5a,7-pentol)

Structure for NP0209734 (1-(6,7-dihydroxy-5-isopropyloctan-2-yl)-9a,11a-dimethyl-dodecahydro-1h-cyclopenta[a]phenanthrene-3,3b,5,5a,7-pentol)

3D Structure for NP0209734 (1-(6,7-dihydroxy-5-isopropyloctan-2-yl)-9a,11a-dimethyl-dodecahydro-1h-cyclopenta[a]phenanthrene-3,3b,5,5a,7-pentol)