NP-MRD: Showing NP-Card for (1r,3r,3as,3br,5s,5as,7s,9ar,9bs,11ar)-1-[(2r,3e,5r,6r)-7-hydroxy-4,5,6-trimethylhept-3-en-2-yl]-9a,11a-dimethyl-tetradecahydro-1h-cyclopenta[a]phenanthrene-3,5,7-triol (NP0245900)

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Record Information

Version

2.0

Created at

2022-09-07 07:09:19 UTC

Updated at

2022-09-07 07:09:20 UTC

NP-MRD ID

NP0245900

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r,3r,3as,3br,5s,5as,7s,9ar,9bs,11ar)-1-[(2r,3e,5r,6r)-7-hydroxy-4,5,6-trimethylhept-3-en-2-yl]-9a,11a-dimethyl-tetradecahydro-1h-cyclopenta[a]phenanthrene-3,5,7-triol

Description

Certonardosterol j belongs to the class of organic compounds known as gorgostanes and derivatives. These are steroids containing a gorgostane moiety, which a skeleton characterized by the presence. Thus, certonardosterol J is considered to be a sterol. (1r,3r,3as,3br,5s,5as,7s,9ar,9bs,11ar)-1-[(2r,3e,5r,6r)-7-hydroxy-4,5,6-trimethylhept-3-en-2-yl]-9a,11a-dimethyl-tetradecahydro-1h-cyclopenta[a]phenanthrene-3,5,7-triol is found in Certonardoa semiregularis. Based on a literature review very few articles have been published on Certonardosterol j.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309072209092D          

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M  END

     RDKit          3D

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M  END


  Mrv1652309072209092D          

 33 36  0  0  1  0            999 V2000
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    3.4946   -5.4334    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.0009   -4.7820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8055   -6.1975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6227   -6.3104    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  1  0  0  0
  6  4  1  1  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  1  0  0  0
 10  8  1  1  0  0  0
 10 11  1  0  0  0  0
 11 12  1  6  0  0  0
 12 13  1  0  0  0  0
 13 14  1  6  0  0  0
 13 15  1  0  0  0  0
 15 16  1  1  0  0  0
 16 17  1  0  0  0  0
 17 18  1  1  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 15 21  1  0  0  0  0
 21 22  1  1  0  0  0
 21 23  1  0  0  0  0
 11 23  1  0  0  0  0
 23 24  1  1  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 10 26  1  0  0  0  0
  6 26  1  0  0  0  0
 26 27  1  1  0  0  0
  2 28  1  0  0  0  0
 28 29  1  1  0  0  0
 28 30  1  0  0  0  0
 30 31  1  1  0  0  0
 30 32  1  0  0  0  0
 32 33  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0245900

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H](CO)[C@@H](C)C(\C)=C\[C@@H](C)[C@H]1C[C@@H](O)[C@H]2[C@@H]3C[C@H](O)[C@H]4C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@]12C

> <INCHI_IDENTIFIER>
InChI=1S/C29H50O4/c1-16(19(4)18(3)15-30)11-17(2)23-14-26(33)27-21-13-25(32)24-12-20(31)7-9-28(24,5)22(21)8-10-29(23,27)6/h11,17-27,30-33H,7-10,12-15H2,1-6H3/b16-11+/t17-,18+,19+,20+,21-,22+,23-,24-,25+,26-,27-,28-,29-/m1/s1

> <INCHI_KEY>
GEUZMMXOSWUBAU-XWKDZGFSSA-N

> <FORMULA>
C29H50O4

> <MOLECULAR_WEIGHT>
462.715

> <EXACT_MASS>
462.37091009

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
83

> <JCHEM_AVERAGE_POLARIZABILITY>
56.60748642178445

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,2R,5S,7S,8S,10R,11S,12R,14R,15R)-14-[(2R,3E,5R,6R)-7-hydroxy-4,5,6-trimethylhept-3-en-2-yl]-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecane-5,8,12-triol

> <JCHEM_LOGP>
3.710672742666667

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.420097304032424

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.751498124416088

> <JCHEM_PKA_STRONGEST_BASIC>
-0.6016511040902411

> <JCHEM_POLAR_SURFACE_AREA>
80.92

> <JCHEM_REFRACTIVITY>
134.75039999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2R,5S,7S,8S,10R,11S,12R,14R,15R)-14-[(2R,3E,5R,6R)-7-hydroxy-4,5,6-trimethylhept-3-en-2-yl]-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecane-5,8,12-triol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 07-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-SEP-22         0                                  
HETATM    1  C   UNK     0       2.892  -8.295   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.417  -8.505   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.363  -7.289   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.782  -5.863   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.257  -5.652   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.727  -4.647   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.299  -3.168   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.574  -2.304   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       6.624  -0.764   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       7.790  -3.249   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       9.306  -2.978   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       9.829  -1.529   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      11.345  -1.258   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      11.868   0.190   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      12.338  -2.436   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      13.854  -2.164   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      14.846  -3.342   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      16.362  -3.071   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      14.323  -4.790   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      12.807  -5.061   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      11.814  -3.884   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      11.291  -5.332   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      10.299  -4.155   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       9.775  -5.603   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       8.259  -5.874   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       7.267  -4.697   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       6.595  -6.083   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       4.998  -9.932   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       4.053 -11.147   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       6.523 -10.142   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       7.468  -8.926   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       7.104 -11.569   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       8.629 -11.779   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   28                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7   26                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   26                                                  
CONECT   11   10   12   23                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16   21                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   15   22   23                                             
CONECT   22   21                                                            
CONECT   23   21   11   24                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   10    6   27                                             
CONECT   27   26                                                            
CONECT   28    2   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30   33                                                       
CONECT   33   32                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   72    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₉H₅₀O₄

Average Mass

462.7150 Da

Monoisotopic Mass

462.37091 Da

IUPAC Name

(1S,2R,5S,7S,8S,10R,11S,12R,14R,15R)-14-[(2R,3E,5R,6R)-7-hydroxy-4,5,6-trimethylhept-3-en-2-yl]-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecane-5,8,12-triol

Traditional Name

(1S,2R,5S,7S,8S,10R,11S,12R,14R,15R)-14-[(2R,3E,5R,6R)-7-hydroxy-4,5,6-trimethylhept-3-en-2-yl]-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecane-5,8,12-triol

CAS Registry Number

Not Available

SMILES

C[C@@H](CO)[C@@H](C)C(\C)=C\[C@@H](C)[C@H]1C[C@@H](O)[C@H]2[C@@H]3C[C@H](O)[C@H]4C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@]12C

InChI Identifier

InChI=1S/C29H50O4/c1-16(19(4)18(3)15-30)11-17(2)23-14-26(33)27-21-13-25(32)24-12-20(31)7-9-28(24,5)22(21)8-10-29(23,27)6/h11,17-27,30-33H,7-10,12-15H2,1-6H3/b16-11+/t17-,18+,19+,20+,21-,22+,23-,24-,25+,26-,27-,28-,29-/m1/s1

InChI Key

GEUZMMXOSWUBAU-XWKDZGFSSA-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 gorgostanes and derivatives. These are steroids containing a gorgostane moiety, which a skeleton characterized by the presence.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Gorgostanes and derivatives

Direct Parent

Gorgostanes and derivatives

Alternative Parents

Substituents

Gorgostane-skeleton
26-hydroxysteroid
3-hydroxysteroid
6-hydroxysteroid
3-beta-hydroxysteroid
15-hydroxysteroid
Hydroxysteroid
Fatty alcohol
Fatty acyl
Cyclic alcohol
Secondary alcohol
Polyol
Primary alcohol
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	3.71	ChemAxon
pKa (Strongest Acidic)	14.75	ChemAxon
pKa (Strongest Basic)	-0.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	80.92 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	134.75 m³·mol⁻¹	ChemAxon
Polarizability	56.61 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	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

10258017

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

21629553

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,3br,5s,5as,7s,9ar,9bs,11ar)-1-[(2r,3e,5r,6r)-7-hydroxy-4,5,6-trimethylhept-3-en-2-yl]-9a,11a-dimethyl-tetradecahydro-1h-cyclopenta[a]phenanthrene-3,5,7-triol (NP0245900)

MOL for NP0245900 ((1r,3r,3as,3br,5s,5as,7s,9ar,9bs,11ar)-1-[(2r,3e,5r,6r)-7-hydroxy-4,5,6-trimethylhept-3-en-2-yl]-9a,11a-dimethyl-tetradecahydro-1h-cyclopenta[a]phenanthrene-3,5,7-triol)

3D MOL for NP0245900 ((1r,3r,3as,3br,5s,5as,7s,9ar,9bs,11ar)-1-[(2r,3e,5r,6r)-7-hydroxy-4,5,6-trimethylhept-3-en-2-yl]-9a,11a-dimethyl-tetradecahydro-1h-cyclopenta[a]phenanthrene-3,5,7-triol)

3D SDF for NP0245900 ((1r,3r,3as,3br,5s,5as,7s,9ar,9bs,11ar)-1-[(2r,3e,5r,6r)-7-hydroxy-4,5,6-trimethylhept-3-en-2-yl]-9a,11a-dimethyl-tetradecahydro-1h-cyclopenta[a]phenanthrene-3,5,7-triol)

3D-SDF for NP0245900 ((1r,3r,3as,3br,5s,5as,7s,9ar,9bs,11ar)-1-[(2r,3e,5r,6r)-7-hydroxy-4,5,6-trimethylhept-3-en-2-yl]-9a,11a-dimethyl-tetradecahydro-1h-cyclopenta[a]phenanthrene-3,5,7-triol)

PDB for NP0245900 ((1r,3r,3as,3br,5s,5as,7s,9ar,9bs,11ar)-1-[(2r,3e,5r,6r)-7-hydroxy-4,5,6-trimethylhept-3-en-2-yl]-9a,11a-dimethyl-tetradecahydro-1h-cyclopenta[a]phenanthrene-3,5,7-triol)

3D PDB for NP0245900 ((1r,3r,3as,3br,5s,5as,7s,9ar,9bs,11ar)-1-[(2r,3e,5r,6r)-7-hydroxy-4,5,6-trimethylhept-3-en-2-yl]-9a,11a-dimethyl-tetradecahydro-1h-cyclopenta[a]phenanthrene-3,5,7-triol)

SMILES for NP0245900 ((1r,3r,3as,3br,5s,5as,7s,9ar,9bs,11ar)-1-[(2r,3e,5r,6r)-7-hydroxy-4,5,6-trimethylhept-3-en-2-yl]-9a,11a-dimethyl-tetradecahydro-1h-cyclopenta[a]phenanthrene-3,5,7-triol)

INCHI for NP0245900 ((1r,3r,3as,3br,5s,5as,7s,9ar,9bs,11ar)-1-[(2r,3e,5r,6r)-7-hydroxy-4,5,6-trimethylhept-3-en-2-yl]-9a,11a-dimethyl-tetradecahydro-1h-cyclopenta[a]phenanthrene-3,5,7-triol)

Structure for NP0245900 ((1r,3r,3as,3br,5s,5as,7s,9ar,9bs,11ar)-1-[(2r,3e,5r,6r)-7-hydroxy-4,5,6-trimethylhept-3-en-2-yl]-9a,11a-dimethyl-tetradecahydro-1h-cyclopenta[a]phenanthrene-3,5,7-triol)

3D Structure for NP0245900 ((1r,3r,3as,3br,5s,5as,7s,9ar,9bs,11ar)-1-[(2r,3e,5r,6r)-7-hydroxy-4,5,6-trimethylhept-3-en-2-yl]-9a,11a-dimethyl-tetradecahydro-1h-cyclopenta[a]phenanthrene-3,5,7-triol)