NP-MRD: Showing NP-Card for 7,10-dihydroxy-3a,6,9a,11a-tetramethyl-1-(6-methyl-5-methylideneheptan-2-yl)-1h,2h,3h,5h,5ah,6h,7h,8h,9h,10h,11h-cyclopenta[a]phenanthren-4-one (NP0226768)

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Record Information

Version

2.0

Created at

2022-09-06 05:54:57 UTC

Updated at

2022-09-06 05:54:57 UTC

NP-MRD ID

NP0226768

Secondary Accession Numbers

None

Natural Product Identification

Common Name

7,10-dihydroxy-3a,6,9a,11a-tetramethyl-1-(6-methyl-5-methylideneheptan-2-yl)-1h,2h,3h,5h,5ah,6h,7h,8h,9h,10h,11h-cyclopenta[a]phenanthren-4-one

Description

5,17-Dihydroxy-2,6,11,15-tetramethyl-14-(6-methyl-5-methylideneheptan-2-yl)tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadec-1(10)-en-9-one belongs to the class of organic compounds known as ergosterols and derivatives. These are steroids containing ergosta-5,7,22-trien-3beta-ol or a derivative thereof, which is based on the 3beta-hydroxylated ergostane skeleton. 7,10-dihydroxy-3a,6,9a,11a-tetramethyl-1-(6-methyl-5-methylideneheptan-2-yl)-1h,2h,3h,5h,5ah,6h,7h,8h,9h,10h,11h-cyclopenta[a]phenanthren-4-one is found in Euphorbia chamaesyce. 5,17-Dihydroxy-2,6,11,15-tetramethyl-14-(6-methyl-5-methylideneheptan-2-yl)tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadec-1(10)-en-9-one is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004171522292D          

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M  END

     RDKit          3D

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M  END


  Mrv1533004171522292D          

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    8.3978   -7.7200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0388   -7.2785    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7838   -8.0631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9768   -8.2346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7219   -9.0192    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  2  0  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  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
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 10 20  1  0  0  0  0
 13 20  1  0  0  0  0
 20 21  1  0  0  0  0
 16 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 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
 22 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 15 32  1  0  0  0  0
 32 33  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0226768

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)C(=C)CCC(C)C1CCC2(C)C3=C(C(O)CC12C)C1(C)CCC(O)C(C)C1CC3=O

> <INCHI_IDENTIFIER>
InChI=1S/C30H48O3/c1-17(2)18(3)9-10-19(4)21-11-14-29(7)27-24(32)15-22-20(5)23(31)12-13-28(22,6)26(27)25(33)16-30(21,29)8/h17,19-23,25,31,33H,3,9-16H2,1-2,4-8H3

> <INCHI_KEY>
AICUYZKXEQURMH-UHFFFAOYSA-N

> <FORMULA>
C30H48O3

> <MOLECULAR_WEIGHT>
456.711

> <EXACT_MASS>
456.360345406

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
81

> <JCHEM_AVERAGE_POLARIZABILITY>
56.01659236434504

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
5,17-dihydroxy-2,6,11,15-tetramethyl-14-(6-methyl-5-methylideneheptan-2-yl)tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-1(10)-en-9-one

> <ALOGPS_LOGP>
5.33

> <JCHEM_LOGP>
5.775530009333332

> <ALOGPS_LOGS>
-5.13

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
19.022496218944376

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.521040008573163

> <JCHEM_PKA_STRONGEST_BASIC>
-1.0393572160647548

> <JCHEM_POLAR_SURFACE_AREA>
57.53

> <JCHEM_REFRACTIVITY>
135.8314

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.37e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5,17-dihydroxy-2,6,11,15-tetramethyl-14-(6-methyl-5-methylideneheptan-2-yl)tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-1(10)-en-9-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 17-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-APR-15         0                                  
HETATM    1  C   UNK     0      -1.819 -14.029   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.486 -13.259   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.486 -11.719   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.848 -14.029   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.848 -15.569   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.182 -13.259   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.515 -14.029   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.849 -13.259   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.849 -11.719   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.183 -14.029   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.344 -15.560   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.850 -15.881   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.620 -14.547   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.525 -15.793   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      10.126 -14.227   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      10.602 -12.762   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       9.572 -11.618   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      10.048 -10.153   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       8.065 -11.938   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       7.590 -13.403   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       6.445 -12.372   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      12.109 -12.442   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      11.078 -11.298   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      12.584 -10.977   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      14.091 -10.657   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      15.121 -11.802   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      16.628 -11.481   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      14.645 -13.266   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      15.676 -14.411   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      13.139 -13.586   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      12.663 -15.051   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      11.157 -15.371   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      10.681 -16.836   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   20                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   15   20                                             
CONECT   14   13                                                            
CONECT   15   13   16   32                                                  
CONECT   16   15   17   22                                                  
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20                                                       
CONECT   20   19   10   13   21                                             
CONECT   21   20                                                            
CONECT   22   16   23   24   30                                             
CONECT   23   22                                                            
CONECT   24   22   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   22   31                                                  
CONECT   31   30   32                                                       
CONECT   32   31   15   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

C₃₀H₄₈O₃

Average Mass

456.7110 Da

Monoisotopic Mass

456.36035 Da

IUPAC Name

5,17-dihydroxy-2,6,11,15-tetramethyl-14-(6-methyl-5-methylideneheptan-2-yl)tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-1(10)-en-9-one

Traditional Name

5,17-dihydroxy-2,6,11,15-tetramethyl-14-(6-methyl-5-methylideneheptan-2-yl)tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-1(10)-en-9-one

CAS Registry Number

Not Available

SMILES

CC(C)C(=C)CCC(C)C1CCC2(C)C3=C(C(O)CC12C)C1(C)CCC(O)C(C)C1CC3=O

InChI Identifier

InChI=1S/C30H48O3/c1-17(2)18(3)9-10-19(4)21-11-14-29(7)27-24(32)15-22-20(5)23(31)12-13-28(22,6)26(27)25(33)16-30(21,29)8/h17,19-23,25,31,33H,3,9-16H2,1-2,4-8H3

InChI Key

AICUYZKXEQURMH-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
Euphorbia chamaesyce	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as ergosterols and derivatives. These are steroids containing ergosta-5,7,22-trien-3beta-ol or a derivative thereof, which is based on the 3beta-hydroxylated ergostane skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Ergostane steroids

Direct Parent

Ergosterols and derivatives

Alternative Parents

Substituents

Ergosterol-skeleton
3-hydroxysteroid
Hydroxysteroid
7-oxosteroid
11-hydroxysteroid
Oxosteroid
Cyclohexenone
Cyclic alcohol
Ketone
Secondary alcohol
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Carbonyl group
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	5.33	ALOGPS
logP	5.78	ChemAxon
logS	-5.1	ALOGPS
pKa (Strongest Acidic)	14.52	ChemAxon
pKa (Strongest Basic)	-1	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	5	ChemAxon
Refractivity	135.83 m³·mol⁻¹	ChemAxon
Polarizability	56.02 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	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

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

85172650

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 7,10-dihydroxy-3a,6,9a,11a-tetramethyl-1-(6-methyl-5-methylideneheptan-2-yl)-1h,2h,3h,5h,5ah,6h,7h,8h,9h,10h,11h-cyclopenta[a]phenanthren-4-one (NP0226768)

MOL for NP0226768 (7,10-dihydroxy-3a,6,9a,11a-tetramethyl-1-(6-methyl-5-methylideneheptan-2-yl)-1h,2h,3h,5h,5ah,6h,7h,8h,9h,10h,11h-cyclopenta[a]phenanthren-4-one)

3D MOL for NP0226768 (7,10-dihydroxy-3a,6,9a,11a-tetramethyl-1-(6-methyl-5-methylideneheptan-2-yl)-1h,2h,3h,5h,5ah,6h,7h,8h,9h,10h,11h-cyclopenta[a]phenanthren-4-one)

3D SDF for NP0226768 (7,10-dihydroxy-3a,6,9a,11a-tetramethyl-1-(6-methyl-5-methylideneheptan-2-yl)-1h,2h,3h,5h,5ah,6h,7h,8h,9h,10h,11h-cyclopenta[a]phenanthren-4-one)

3D-SDF for NP0226768 (7,10-dihydroxy-3a,6,9a,11a-tetramethyl-1-(6-methyl-5-methylideneheptan-2-yl)-1h,2h,3h,5h,5ah,6h,7h,8h,9h,10h,11h-cyclopenta[a]phenanthren-4-one)

PDB for NP0226768 (7,10-dihydroxy-3a,6,9a,11a-tetramethyl-1-(6-methyl-5-methylideneheptan-2-yl)-1h,2h,3h,5h,5ah,6h,7h,8h,9h,10h,11h-cyclopenta[a]phenanthren-4-one)

3D PDB for NP0226768 (7,10-dihydroxy-3a,6,9a,11a-tetramethyl-1-(6-methyl-5-methylideneheptan-2-yl)-1h,2h,3h,5h,5ah,6h,7h,8h,9h,10h,11h-cyclopenta[a]phenanthren-4-one)

SMILES for NP0226768 (7,10-dihydroxy-3a,6,9a,11a-tetramethyl-1-(6-methyl-5-methylideneheptan-2-yl)-1h,2h,3h,5h,5ah,6h,7h,8h,9h,10h,11h-cyclopenta[a]phenanthren-4-one)

INCHI for NP0226768 (7,10-dihydroxy-3a,6,9a,11a-tetramethyl-1-(6-methyl-5-methylideneheptan-2-yl)-1h,2h,3h,5h,5ah,6h,7h,8h,9h,10h,11h-cyclopenta[a]phenanthren-4-one)

Structure for NP0226768 (7,10-dihydroxy-3a,6,9a,11a-tetramethyl-1-(6-methyl-5-methylideneheptan-2-yl)-1h,2h,3h,5h,5ah,6h,7h,8h,9h,10h,11h-cyclopenta[a]phenanthren-4-one)

3D Structure for NP0226768 (7,10-dihydroxy-3a,6,9a,11a-tetramethyl-1-(6-methyl-5-methylideneheptan-2-yl)-1h,2h,3h,5h,5ah,6h,7h,8h,9h,10h,11h-cyclopenta[a]phenanthren-4-one)