NP-MRD: Showing NP-Card for Oogoniol (NP0066392)

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Record Information

Version

2.0

Created at

2022-04-28 10:39:43 UTC

Updated at

2022-04-28 10:39:44 UTC

NP-MRD ID

NP0066392

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Oogoniol

Description

SCHEMBL8500637 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. Oogoniol is found in Achlya bisexualis and Achlya heterosexualis. Based on a literature review very few articles have been published on SCHEMBL8500637.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282212392D          

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  1 11  1  0  0  0  0
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  9 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 16 15  1  1  0  0  0
  8 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
 15 19  1  0  0  0  0
 19 20  1  1  0  0  0
 20 21  1  6  0  0  0
 20 22  1  0  0  0  0
 22 23  1  0  0  0  0
 24 23  1  6  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 24 28  1  0  0  0  0
 28 29  1  0  0  0  0
 28 30  1  0  0  0  0
 17 31  1  1  0  0  0
 15 32  1  1  0  0  0
 13 33  1  6  0  0  0
  2 34  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0066392

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)[C@@H](CCO)CC[C@@H](C)[C@H]1C[C@@H](O)[C@H]2[C@H]3[C@H]([C@H](O)C[C@]12C)[C@@]1(C)CC[C@H](O)CC1=CC3=O

> <INCHI_IDENTIFIER>
InChI=1S/C29H48O5/c1-16(2)18(9-11-30)7-6-17(3)21-14-23(33)26-25-22(32)13-19-12-20(31)8-10-28(19,4)27(25)24(34)15-29(21,26)5/h13,16-18,20-21,23-27,30-31,33-34H,6-12,14-15H2,1-5H3/t17-,18-,20+,21-,23-,24-,25+,26+,27+,28+,29-/m1/s1

> <INCHI_KEY>
QQEXUEXZMINFCW-ZHVYCVCCSA-N

> <FORMULA>
C29H48O5

> <MOLECULAR_WEIGHT>
476.698

> <EXACT_MASS>
476.350174646

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
82

> <JCHEM_AVERAGE_POLARIZABILITY>
57.20256193033083

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,2R,5S,10S,11S,12R,14R,15R,17R)-5,12,17-trihydroxy-14-[(2R,5R)-7-hydroxy-5-(propan-2-yl)heptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-9-one

> <ALOGPS_LOGP>
3.19

> <JCHEM_LOGP>
3.2267631843333326

> <ALOGPS_LOGS>
-4.27

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.190604695192075

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.571857702046238

> <JCHEM_PKA_STRONGEST_BASIC>
-1.2528514610659989

> <JCHEM_POLAR_SURFACE_AREA>
97.99000000000001

> <JCHEM_REFRACTIVITY>
135.52379999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.58e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2R,5S,10S,11S,12R,14R,15R,17R)-5,12,17-trihydroxy-14-[(2R,5R)-7-hydroxy-5-isopropylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-9-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0      -4.461   7.172   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -5.492   6.028   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -5.016   4.563   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -3.510   4.243   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -3.034   2.779   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.527   2.458   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -1.051   0.994   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -0.497   3.603   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.973   5.067   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -2.479   5.388   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -2.955   6.852   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.449   6.532   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.058   6.212   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.564   5.892   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.040   4.427   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.010   3.283   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.780   1.949   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.286   2.269   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.447   3.801   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.781   4.571   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.781   6.111   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       6.114   3.801   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       7.448   4.571   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       8.782   3.801   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      10.115   4.571   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      11.449   3.801   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      12.783   4.571   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       8.782   2.261   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      10.115   1.491   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       7.448   1.491   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       1.153   0.542   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       3.184   5.458   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      -0.418   7.677   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0      -6.998   6.348   0.000  0.00  0.00           O+0
CONECT    1    2   11                                                       
CONECT    2    1    3   34                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   10                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   16                                                  
CONECT    9    8   10   13                                                  
CONECT   10    9    4   11   12                                             
CONECT   11   10    1                                                       
CONECT   12   10                                                            
CONECT   13    9   14   33                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   19   32                                             
CONECT   16   15    8   17                                                  
CONECT   17   16   18   31                                                  
CONECT   18   17   19                                                       
CONECT   19   18   15   20                                                  
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25   28                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26                                                            
CONECT   28   24   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28                                                            
CONECT   31   17                                                            
CONECT   32   15                                                            
CONECT   33   13                                                            
CONECT   34    2                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   74    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₉H₄₈O₅

Average Mass

476.6980 Da

Monoisotopic Mass

476.35017 Da

IUPAC Name

(1S,2R,5S,10S,11S,12R,14R,15R,17R)-5,12,17-trihydroxy-14-[(2R,5R)-7-hydroxy-5-(propan-2-yl)heptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-9-one

Traditional Name

(1S,2R,5S,10S,11S,12R,14R,15R,17R)-5,12,17-trihydroxy-14-[(2R,5R)-7-hydroxy-5-isopropylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-9-one

CAS Registry Number

Not Available

SMILES

CC(C)[C@@H](CCO)CC[C@@H](C)[C@H]1C[C@@H](O)[C@H]2[C@H]3[C@H]([C@H](O)C[C@]12C)[C@@]1(C)CC[C@H](O)CC1=CC3=O

InChI Identifier

InChI=1S/C29H48O5/c1-16(2)18(9-11-30)7-6-17(3)21-14-23(33)26-25-22(32)13-19-12-20(31)8-10-28(19,4)27(25)24(34)15-29(21,26)5/h13,16-18,20-21,23-27,30-31,33-34H,6-12,14-15H2,1-5H3/t17-,18-,20+,21-,23-,24-,25+,26+,27+,28+,29-/m1/s1

InChI Key

QQEXUEXZMINFCW-ZHVYCVCCSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Achlya bisexualis	Animalia	KNApSAcK
Achlya heterosexualis	Animalia	KNApSAcK

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

C24-propyl-sterol-skeleton
Triterpenoid
Stigmastane-skeleton
3-hydroxy-delta-5-steroid
3-hydroxysteroid
15-hydroxysteroid
Hydroxysteroid
7-oxosteroid
3-beta-hydroxysteroid
11-hydroxysteroid
11-alpha-hydroxysteroid
3-beta-hydroxy-delta-5-steroid
Oxosteroid
Delta-5-steroid
Fatty alcohol
Cyclohexenone
Fatty acyl
Cyclic alcohol
Secondary alcohol
Ketone
Polyol
Organooxygen compound
Hydrocarbon derivative
Organic oxygen compound
Carbonyl group
Alcohol
Organic oxide
Primary 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	3.19	ALOGPS
logP	3.23	ChemAxon
logS	-4.3	ALOGPS
pKa (Strongest Acidic)	14.57	ChemAxon
pKa (Strongest Basic)	-1.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	97.99 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	135.52 m³·mol⁻¹	ChemAxon
Polarizability	57.2 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	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

10378744

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

14238091

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Oogoniol (NP0066392)

MOL for NP0066392 (Oogoniol)

3D MOL for NP0066392 (Oogoniol)

3D SDF for NP0066392 (Oogoniol)

3D-SDF for NP0066392 (Oogoniol)

PDB for NP0066392 (Oogoniol)

3D PDB for NP0066392 (Oogoniol)

SMILES for NP0066392 (Oogoniol)

INCHI for NP0066392 (Oogoniol)

Structure for NP0066392 (Oogoniol)

3D Structure for NP0066392 (Oogoniol)