NP-MRD: Showing NP-Card for 1-(5-ethyl-3-hydroxy-6-methylheptan-2-yl)-7-hydroxy-9a,11a-dimethyl-1h,2h,3h,3ah,3bh,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-4-one (NP0172643)

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Record Information

Version

2.0

Created at

2022-09-03 09:36:36 UTC

Updated at

2022-09-03 09:36:37 UTC

NP-MRD ID

NP0172643

Secondary Accession Numbers

None

Natural Product Identification

Common Name

1-(5-ethyl-3-hydroxy-6-methylheptan-2-yl)-7-hydroxy-9a,11a-dimethyl-1h,2h,3h,3ah,3bh,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-4-one

Description

Schleicherastatin 5 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. Schleicherastatin 5 is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, schleicherastatin 5 has been detected, but not quantified in, fruits. 1-(5-ethyl-3-hydroxy-6-methylheptan-2-yl)-7-hydroxy-9a,11a-dimethyl-1h,2h,3h,3ah,3bh,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-4-one is found in Schleichera oleosa. This could make schleicherastatin 5 a potential biomarker for the consumption of these foods.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 02241208402D          

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M  END

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M  END


  Mrv0541 02241208402D          

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  5 10  2  0  0  0  0
  7  8  1  0  0  0  0
  7 11  1  0  0  0  0
  8  9  1  0  0  0  0
  8 14  1  0  0  0  0
  9 10  1  0  0  0  0
  9 21  2  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
 13 32  1  0  0  0  0
 14 17  1  0  0  0  0
 15 16  1  0  0  0  0
 15 18  1  0  0  0  0
 16 17  1  0  0  0  0
 18 22  1  0  0  0  0
 18 30  1  0  0  0  0
 22 23  1  0  0  0  0
 22 31  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 24 27  1  0  0  0  0
 25 26  1  0  0  0  0
 25 29  1  0  0  0  0
 27 28  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0172643

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCC(CC(O)C(C)C1CCC2C3C(CCC12C)C1(C)CCC(O)CC1=CC3=O)C(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C29H48O3/c1-7-19(17(2)3)14-25(31)18(4)22-8-9-23-27-24(11-13-29(22,23)6)28(5)12-10-21(30)15-20(28)16-26(27)32/h16-19,21-25,27,30-31H,7-15H2,1-6H3

> <INCHI_KEY>
XWLHFTUCQDCSTJ-UHFFFAOYSA-N

> <FORMULA>
C29H48O3

> <MOLECULAR_WEIGHT>
444.6896

> <EXACT_MASS>
444.360345402

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
54.418739884966534

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
14-(5-ethyl-3-hydroxy-6-methylheptan-2-yl)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-9-one

> <ALOGPS_LOGP>
5.01

> <JCHEM_LOGP>
5.972206598000001

> <ALOGPS_LOGS>
-5.16

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
18.270745923091404

> <JCHEM_PKA_STRONGEST_ACIDIC>
17.38833010645442

> <JCHEM_PKA_STRONGEST_BASIC>
-0.5843642472725484

> <JCHEM_POLAR_SURFACE_AREA>
57.53

> <JCHEM_REFRACTIVITY>
132.00259999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.10e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
14-(5-ethyl-3-hydroxy-6-methylheptan-2-yl)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-9-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      -5.349  -5.459   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -5.349  -3.916   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -4.015  -3.145   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.683  -3.916   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.683  -5.459   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -4.015  -6.227   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.348  -3.145   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.017  -3.916   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.017  -5.459   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.348  -6.227   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.348  -1.604   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.017  -0.836   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.313  -1.604   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.313  -3.145   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.776  -1.129   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.675  -2.373   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.776  -3.613   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.254   0.337   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -2.683  -2.373   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      -6.684  -6.227   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       1.313  -6.227   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       4.740   0.738   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       5.141   2.224   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       4.372   3.559   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       5.141   4.893   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       4.372   6.227   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       2.835   3.559   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       2.061   4.893   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       6.684   4.893   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       2.192   1.455   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       5.830  -0.352   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       1.313  -0.062   0.000  0.00  0.00           C+0
CONECT    1    2    6   20                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5    7   19                                             
CONECT    5    4    6   10                                                  
CONECT    6    1    5                                                       
CONECT    7    4    8   11                                                  
CONECT    8    7    9   14                                                  
CONECT    9    8   10   21                                                  
CONECT   10    5    9                                                       
CONECT   11    7   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   15   32                                             
CONECT   14    8   13   17                                                  
CONECT   15   13   16   18                                                  
CONECT   16   15   17                                                       
CONECT   17   14   16                                                       
CONECT   18   15   22   30                                                  
CONECT   19    4                                                            
CONECT   20    1                                                            
CONECT   21    9                                                            
CONECT   22   18   23   31                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25   27                                                  
CONECT   25   24   26   29                                                  
CONECT   26   25                                                            
CONECT   27   24   28                                                       
CONECT   28   27                                                            
CONECT   29   25                                                            
CONECT   30   18                                                            
CONECT   31   22                                                            
CONECT   32   13                                                            
MASTER        0    0    0    0    0    0    0    0   32    0   70    0
END

View in JSmol

Synonyms

Value	Source
3,22-Dihydroxystigmast-5-en-7-one	HMDB

Chemical Formula

C₂₉H₄₈O₃

Average Mass

444.6896 Da

Monoisotopic Mass

444.36035 Da

IUPAC Name

14-(5-ethyl-3-hydroxy-6-methylheptan-2-yl)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-9-one

Traditional Name

14-(5-ethyl-3-hydroxy-6-methylheptan-2-yl)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-9-one

CAS Registry Number

Not Available

SMILES

CCC(CC(O)C(C)C1CCC2C3C(CCC12C)C1(C)CCC(O)CC1=CC3=O)C(C)C

InChI Identifier

InChI=1S/C29H48O3/c1-7-19(17(2)3)14-25(31)18(4)22-8-9-23-27-24(11-13-29(22,23)6)28(5)12-10-21(30)15-20(28)16-26(27)32/h16-19,21-25,27,30-31H,7-15H2,1-6H3

InChI Key

XWLHFTUCQDCSTJ-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
Schleichera oleosa	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

Not Available

Substituents

Not Available

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	5.01	ALOGPS
logP	5.97	ChemAxon
logS	-5.2	ALOGPS
pKa (Strongest Acidic)	17.39	ChemAxon
pKa (Strongest Basic)	-0.58	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	57.53 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	132 m³·mol⁻¹	ChemAxon
Polarizability	54.42 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

HMDB0035804

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB014556

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

73105735

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 1-(5-ethyl-3-hydroxy-6-methylheptan-2-yl)-7-hydroxy-9a,11a-dimethyl-1h,2h,3h,3ah,3bh,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-4-one (NP0172643)

MOL for NP0172643 (1-(5-ethyl-3-hydroxy-6-methylheptan-2-yl)-7-hydroxy-9a,11a-dimethyl-1h,2h,3h,3ah,3bh,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-4-one)

3D MOL for NP0172643 (1-(5-ethyl-3-hydroxy-6-methylheptan-2-yl)-7-hydroxy-9a,11a-dimethyl-1h,2h,3h,3ah,3bh,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-4-one)

3D SDF for NP0172643 (1-(5-ethyl-3-hydroxy-6-methylheptan-2-yl)-7-hydroxy-9a,11a-dimethyl-1h,2h,3h,3ah,3bh,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-4-one)

3D-SDF for NP0172643 (1-(5-ethyl-3-hydroxy-6-methylheptan-2-yl)-7-hydroxy-9a,11a-dimethyl-1h,2h,3h,3ah,3bh,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-4-one)

PDB for NP0172643 (1-(5-ethyl-3-hydroxy-6-methylheptan-2-yl)-7-hydroxy-9a,11a-dimethyl-1h,2h,3h,3ah,3bh,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-4-one)

3D PDB for NP0172643 (1-(5-ethyl-3-hydroxy-6-methylheptan-2-yl)-7-hydroxy-9a,11a-dimethyl-1h,2h,3h,3ah,3bh,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-4-one)

SMILES for NP0172643 (1-(5-ethyl-3-hydroxy-6-methylheptan-2-yl)-7-hydroxy-9a,11a-dimethyl-1h,2h,3h,3ah,3bh,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-4-one)

INCHI for NP0172643 (1-(5-ethyl-3-hydroxy-6-methylheptan-2-yl)-7-hydroxy-9a,11a-dimethyl-1h,2h,3h,3ah,3bh,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-4-one)

Structure for NP0172643 (1-(5-ethyl-3-hydroxy-6-methylheptan-2-yl)-7-hydroxy-9a,11a-dimethyl-1h,2h,3h,3ah,3bh,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-4-one)

3D Structure for NP0172643 (1-(5-ethyl-3-hydroxy-6-methylheptan-2-yl)-7-hydroxy-9a,11a-dimethyl-1h,2h,3h,3ah,3bh,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-4-one)