NP-MRD: Showing NP-Card for (1r,3r,3as,3bs,5s,5as,6r,7s,9as,9br,11ar)-1-[(2r,5r,6s)-7-hydroxy-5,6-dimethylheptan-2-yl]-9a,11a-dimethyl-tetradecahydrocyclopenta[a]phenanthrene-3,3b,5,6,7-pentol (NP0289557)

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Record Information

Version

2.0

Created at

2022-09-09 19:48:37 UTC

Updated at

2022-09-09 19:48:37 UTC

NP-MRD ID

NP0289557

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r,3r,3as,3bs,5s,5as,6r,7s,9as,9br,11ar)-1-[(2r,5r,6s)-7-hydroxy-5,6-dimethylheptan-2-yl]-9a,11a-dimethyl-tetradecahydrocyclopenta[a]phenanthrene-3,3b,5,6,7-pentol

Description

Certonardosterol m 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. Thus, certonardosterol m is considered to be a sterol. (1r,3r,3as,3bs,5s,5as,6r,7s,9as,9br,11ar)-1-[(2r,5r,6s)-7-hydroxy-5,6-dimethylheptan-2-yl]-9a,11a-dimethyl-tetradecahydrocyclopenta[a]phenanthrene-3,3b,5,6,7-pentol is found in Certonardoa semiregularis. Based on a literature review very few articles have been published on Certonardosterol m.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309092221482D          

 34 37  0  0  1  0            999 V2000
    7.7104   -3.3261    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    8.4249   -1.2636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1394   -2.5011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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 32 33  1  0  0  0  0
 15 33  1  0  0  0  0
 11 33  1  0  0  0  0
 33 34  1  1  0  0  0
M  END

     RDKit          3D

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M  END


  Mrv1652309092221482D          

 34 37  0  0  1  0            999 V2000
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   14.7123   -3.7234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4574   -2.9388    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   13.9053   -3.5519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6504   -2.7673    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   13.0984   -3.3803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2914   -3.2088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0365   -2.4242    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   11.4234   -2.9762    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6  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  6  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  6  0  0  0
 11  9  1  1  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  1  0  0  0
 15 13  1  1  0  0  0
 15 16  1  0  0  0  0
 16 17  1  1  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  6  0  0  0
 21 19  1  1  0  0  0
 21 22  1  0  0  0  0
 22 23  1  1  0  0  0
 22 24  1  0  0  0  0
 24 25  1  1  0  0  0
 24 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 21 28  1  0  0  0  0
 28 29  1  1  0  0  0
 28 30  1  0  0  0  0
 16 30  1  0  0  0  0
 30 31  1  1  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 15 33  1  0  0  0  0
 11 33  1  0  0  0  0
 33 34  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0289557

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@H](CO)[C@H](C)CC[C@@H](C)[C@H]1C[C@@H](O)[C@@H]2[C@]1(C)CC[C@@H]1[C@@]3(C)CC[C@H](O)[C@H](O)[C@@H]3[C@@H](O)C[C@@]21O

> <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/t15-,16-,17-,18-,19+,20-,21+,22-,23+,24+,25-,26-,27-,28+/m1/s1

> <INCHI_KEY>
QLEHTNPUVWZOQF-ZNCSQDSCSA-N

> <FORMULA>
C28H50O6

> <MOLECULAR_WEIGHT>
482.702

> <EXACT_MASS>
482.36073933

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
84

> <JCHEM_AVERAGE_POLARIZABILITY>
57.085124603645

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,2S,5S,6R,7S,8S,10S,11S,12R,14R,15R)-14-[(2R,5R,6S)-7-hydroxy-5,6-dimethylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecane-5,6,8,10,12-pentol

> <JCHEM_LOGP>
1.5273954736666673

> <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>
132.0772

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2S,5S,6R,7S,8S,10S,11S,12R,14R,15R)-14-[(2R,5R,6S)-7-hydroxy-5,6-dimethylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecane-5,6,8,10,12-pentol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 09-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   09-SEP-22         0                                  
HETATM    1  C   UNK     0      14.393  -6.209   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      14.393  -4.669   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      13.059  -3.899   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      11.725  -4.669   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      15.726  -3.899   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      15.726  -2.359   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      17.060  -4.669   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      18.394  -3.899   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      19.728  -4.669   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      19.728  -6.209   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      21.061  -3.899   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      21.222  -2.367   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      22.729  -2.047   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      23.355  -0.640   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      23.499  -3.381   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      25.005  -3.701   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      24.529  -2.236   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      26.035  -2.556   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      27.542  -2.877   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      28.572  -1.732   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      28.018  -4.341   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      29.524  -4.661   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      30.554  -3.517   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      30.000  -6.126   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      31.506  -6.446   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      28.969  -7.271   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      27.463  -6.950   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      26.987  -5.486   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      25.957  -6.630   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      25.481  -5.166   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      24.450  -6.310   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      22.944  -5.990   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      22.468  -4.525   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      21.324  -5.556   0.000  0.00  0.00           C+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   33                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16   33                                                  
CONECT   16   15   17   18   30                                             
CONECT   17   16                                                            
CONECT   18   16   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22   28                                                  
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   21   29   30                                             
CONECT   29   28                                                            
CONECT   30   28   16   31                                                  
CONECT   31   30   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   15   11   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

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

C[C@H](CO)[C@H](C)CC[C@@H](C)[C@H]1C[C@@H](O)[C@@H]2[C@]1(C)CC[C@@H]1[C@@]3(C)CC[C@H](O)[C@H](O)[C@@H]3[C@@H](O)C[C@@]21O

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/t15-,16-,17-,18-,19+,20-,21+,22-,23+,24+,25-,26-,27-,28+/m1/s1

InChI Key

QLEHTNPUVWZOQF-ZNCSQDSCSA-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
3-beta-hydroxysteroid
4-hydroxysteroid
6-hydroxysteroid
15-hydroxysteroid
Hydroxysteroid
Fatty alcohol
Fatty acyl
Cyclic alcohol
Tertiary alcohol
Secondary alcohol
Polyol
Primary alcohol
Alcohol
Hydrocarbon derivative
Organic oxygen compound
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

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

10258021

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

21629557

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1r,3r,3as,3bs,5s,5as,6r,7s,9as,9br,11ar)-1-[(2r,5r,6s)-7-hydroxy-5,6-dimethylheptan-2-yl]-9a,11a-dimethyl-tetradecahydrocyclopenta[a]phenanthrene-3,3b,5,6,7-pentol (NP0289557)

MOL for NP0289557 ((1r,3r,3as,3bs,5s,5as,6r,7s,9as,9br,11ar)-1-[(2r,5r,6s)-7-hydroxy-5,6-dimethylheptan-2-yl]-9a,11a-dimethyl-tetradecahydrocyclopenta[a]phenanthrene-3,3b,5,6,7-pentol)

3D MOL for NP0289557 ((1r,3r,3as,3bs,5s,5as,6r,7s,9as,9br,11ar)-1-[(2r,5r,6s)-7-hydroxy-5,6-dimethylheptan-2-yl]-9a,11a-dimethyl-tetradecahydrocyclopenta[a]phenanthrene-3,3b,5,6,7-pentol)

3D SDF for NP0289557 ((1r,3r,3as,3bs,5s,5as,6r,7s,9as,9br,11ar)-1-[(2r,5r,6s)-7-hydroxy-5,6-dimethylheptan-2-yl]-9a,11a-dimethyl-tetradecahydrocyclopenta[a]phenanthrene-3,3b,5,6,7-pentol)

3D-SDF for NP0289557 ((1r,3r,3as,3bs,5s,5as,6r,7s,9as,9br,11ar)-1-[(2r,5r,6s)-7-hydroxy-5,6-dimethylheptan-2-yl]-9a,11a-dimethyl-tetradecahydrocyclopenta[a]phenanthrene-3,3b,5,6,7-pentol)

PDB for NP0289557 ((1r,3r,3as,3bs,5s,5as,6r,7s,9as,9br,11ar)-1-[(2r,5r,6s)-7-hydroxy-5,6-dimethylheptan-2-yl]-9a,11a-dimethyl-tetradecahydrocyclopenta[a]phenanthrene-3,3b,5,6,7-pentol)

3D PDB for NP0289557 ((1r,3r,3as,3bs,5s,5as,6r,7s,9as,9br,11ar)-1-[(2r,5r,6s)-7-hydroxy-5,6-dimethylheptan-2-yl]-9a,11a-dimethyl-tetradecahydrocyclopenta[a]phenanthrene-3,3b,5,6,7-pentol)

SMILES for NP0289557 ((1r,3r,3as,3bs,5s,5as,6r,7s,9as,9br,11ar)-1-[(2r,5r,6s)-7-hydroxy-5,6-dimethylheptan-2-yl]-9a,11a-dimethyl-tetradecahydrocyclopenta[a]phenanthrene-3,3b,5,6,7-pentol)

INCHI for NP0289557 ((1r,3r,3as,3bs,5s,5as,6r,7s,9as,9br,11ar)-1-[(2r,5r,6s)-7-hydroxy-5,6-dimethylheptan-2-yl]-9a,11a-dimethyl-tetradecahydrocyclopenta[a]phenanthrene-3,3b,5,6,7-pentol)

Structure for NP0289557 ((1r,3r,3as,3bs,5s,5as,6r,7s,9as,9br,11ar)-1-[(2r,5r,6s)-7-hydroxy-5,6-dimethylheptan-2-yl]-9a,11a-dimethyl-tetradecahydrocyclopenta[a]phenanthrene-3,3b,5,6,7-pentol)

3D Structure for NP0289557 ((1r,3r,3as,3bs,5s,5as,6r,7s,9as,9br,11ar)-1-[(2r,5r,6s)-7-hydroxy-5,6-dimethylheptan-2-yl]-9a,11a-dimethyl-tetradecahydrocyclopenta[a]phenanthrene-3,3b,5,6,7-pentol)