NP-MRD: Showing NP-Card for (1r,3ar,5as,7s,9as,11ar)-3a,9a,11a-trimethyl-1-[(2r)-6-methyl-5-methylideneheptan-2-yl]-1h,2h,3h,4h,5h,5ah,6h,7h,8h,9h,10h,11h-cyclopenta[a]phenanthren-7-ol (NP0178099)

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Record Information

Version

2.0

Created at

2022-09-03 16:02:10 UTC

Updated at

2022-09-03 16:02:10 UTC

NP-MRD ID

NP0178099

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r,3ar,5as,7s,9as,11ar)-3a,9a,11a-trimethyl-1-[(2r)-6-methyl-5-methylideneheptan-2-yl]-1h,2h,3h,4h,5h,5ah,6h,7h,8h,9h,10h,11h-cyclopenta[a]phenanthren-7-ol

Description

14Alpha-Methylfecosterol 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. (1r,3ar,5as,7s,9as,11ar)-3a,9a,11a-trimethyl-1-[(2r)-6-methyl-5-methylideneheptan-2-yl]-1h,2h,3h,4h,5h,5ah,6h,7h,8h,9h,10h,11h-cyclopenta[a]phenanthren-7-ol is found in Botrytis cinerea and Ustilago maydis. (1r,3ar,5as,7s,9as,11ar)-3a,9a,11a-trimethyl-1-[(2r)-6-methyl-5-methylideneheptan-2-yl]-1h,2h,3h,4h,5h,5ah,6h,7h,8h,9h,10h,11h-cyclopenta[a]phenanthren-7-ol was first documented in 2009 (PMID: 19670905). Based on a literature review a small amount of articles have been published on 14alpha-Methylfecosterol (PMID: 29515531) (PMID: 19122277).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309032218022D          

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M  END

     RDKit          3D

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M  END


  Mrv1652309032218022D          

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 16 17  1  6  0  0  0
 13 18  1  0  0  0  0
 18 19  1  6  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  6  0  0  0
 22 24  1  0  0  0  0
 25 24  1  6  0  0  0
 18 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 12 27  1  0  0  0  0
  2 28  1  0  0  0  0
 28 29  1  0  0  0  0
 28 30  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0178099

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)C(=C)CC[C@@H](C)[C@H]1CC[C@@]2(C)C3=C(CC[C@]12C)[C@@]1(C)CC[C@H](O)C[C@@H]1CC3

> <INCHI_IDENTIFIER>
InChI=1S/C29H48O/c1-19(2)20(3)8-9-21(4)24-13-16-29(7)26-11-10-22-18-23(30)12-15-27(22,5)25(26)14-17-28(24,29)6/h19,21-24,30H,3,8-18H2,1-2,4-7H3/t21-,22+,23+,24-,27+,28-,29+/m1/s1

> <INCHI_KEY>
OOSRLXVESAEQCR-GLISWAMPSA-N

> <FORMULA>
C29H48O

> <MOLECULAR_WEIGHT>
412.702

> <EXACT_MASS>
412.370516166

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
78

> <JCHEM_AVERAGE_POLARIZABILITY>
52.87101216551339

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S,5S,7S,11R,14R,15R)-2,11,15-trimethyl-14-[(2R)-6-methyl-5-methylideneheptan-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-1(10)-en-5-ol

> <JCHEM_LOGP>
7.3086516113333335

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
18.361385746356767

> <JCHEM_PKA_STRONGEST_BASIC>
-1.32852987454355

> <JCHEM_POLAR_SURFACE_AREA>
20.23

> <JCHEM_REFRACTIVITY>
129.15109999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(2S,5S,7S,11R,14R,15R)-2,11,15-trimethyl-14-[(2R)-6-methyl-5-methylideneheptan-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-1(10)-en-5-ol

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 03-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-SEP-22         0                                  
HETATM    1  C   UNK     0       4.624  -5.731   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.624  -7.271   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.291  -8.041   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.957  -7.271   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.623  -8.041   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.623  -9.581   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.710  -7.271   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.871  -5.739   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.378  -5.419   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -3.148  -6.753   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -4.053  -5.507   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -4.654  -7.073   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -5.130  -8.538   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -4.099  -9.682   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -2.593  -9.362   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -2.117  -7.897   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -0.973  -8.928   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -6.636  -8.858   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -5.606 -10.002   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -7.112 -10.322   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -8.618 -10.643   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -9.649  -9.498   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0     -11.155  -9.818   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      -9.173  -8.033   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -7.667  -7.713   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -7.191  -6.249   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -5.684  -5.928   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       5.958  -8.041   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       7.292  -7.271   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       5.958  -9.581   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   28                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8   16                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   12   16                                             
CONECT   11   10                                                            
CONECT   12   10   13   27                                                  
CONECT   13   12   14   18                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15    7   10   17                                             
CONECT   17   16                                                            
CONECT   18   13   19   20   25                                             
CONECT   19   18                                                            
CONECT   20   18   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25                                                       
CONECT   25   24   18   26                                                  
CONECT   26   25   27                                                       
CONECT   27   26   12                                                       
CONECT   28    2   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28                                                            
MASTER        0    0    0    0    0    0    0    0   30    0   66    0
END

View in JSmol

Synonyms

Value	Source
14a-Methylfecosterol	Generator
14Α-methylfecosterol	Generator

Chemical Formula

C₂₉H₄₈O

Average Mass

412.7020 Da

Monoisotopic Mass

412.37052 Da

IUPAC Name

(2S,5S,7S,11R,14R,15R)-2,11,15-trimethyl-14-[(2R)-6-methyl-5-methylideneheptan-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-1(10)-en-5-ol

Traditional Name

(2S,5S,7S,11R,14R,15R)-2,11,15-trimethyl-14-[(2R)-6-methyl-5-methylideneheptan-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-1(10)-en-5-ol

CAS Registry Number

Not Available

SMILES

CC(C)C(=C)CC[C@@H](C)[C@H]1CC[C@@]2(C)C3=C(CC[C@]12C)[C@@]1(C)CC[C@H](O)C[C@@H]1CC3

InChI Identifier

InChI=1S/C29H48O/c1-19(2)20(3)8-9-21(4)24-13-16-29(7)26-11-10-22-18-23(30)12-15-27(22,5)25(26)14-17-28(24,29)6/h19,21-24,30H,3,8-18H2,1-2,4-7H3/t21-,22+,23+,24-,27+,28-,29+/m1/s1

InChI Key

OOSRLXVESAEQCR-GLISWAMPSA-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
Botrytis cinerea	LOTUS Database	35616633
Ustilago maydis	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
14-alpha-methylsteroid
3-beta-hydroxysteroid
Hydroxysteroid
3-hydroxysteroid
Cyclic alcohol
Secondary alcohol
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
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	7.31	ChemAxon
pKa (Strongest Acidic)	18.36	ChemAxon
pKa (Strongest Basic)	-1.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	20.23 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	129.15 m³·mol⁻¹	ChemAxon
Polarizability	52.87 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	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

10403122

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

13831899

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Lv QZ, Qin YL, Yan L, Wang L, Zhang C, Jiang YY: NSG2 (ORF19.273) Encoding Protein Controls Sensitivity of Candida albicans to Azoles through Regulating the Synthesis of C14-Methylated Sterols. Front Microbiol. 2018 Feb 20;9:218. doi: 10.3389/fmicb.2018.00218. eCollection 2018. [PubMed:29515531 ]
Abe F, Usui K, Hiraki T: Fluconazole modulates membrane rigidity, heterogeneity, and water penetration into the plasma membrane in Saccharomyces cerevisiae. Biochemistry. 2009 Sep 15;48(36):8494-504. doi: 10.1021/bi900578y. [PubMed:19670905 ]
Sun LM, Lv BB, Cheng AX, Wu XZ, Lou HX: The effect of plagiochin E alone and in combination with fluconazole on the ergosterol biosynthesis of Candida albicans. Biol Pharm Bull. 2009 Jan;32(1):36-40. doi: 10.1248/bpb.32.36. [PubMed:19122277 ]
LOTUS database [Link]

Showing NP-Card for (1r,3ar,5as,7s,9as,11ar)-3a,9a,11a-trimethyl-1-[(2r)-6-methyl-5-methylideneheptan-2-yl]-1h,2h,3h,4h,5h,5ah,6h,7h,8h,9h,10h,11h-cyclopenta[a]phenanthren-7-ol (NP0178099)

MOL for NP0178099 ((1r,3ar,5as,7s,9as,11ar)-3a,9a,11a-trimethyl-1-[(2r)-6-methyl-5-methylideneheptan-2-yl]-1h,2h,3h,4h,5h,5ah,6h,7h,8h,9h,10h,11h-cyclopenta[a]phenanthren-7-ol)

3D MOL for NP0178099 ((1r,3ar,5as,7s,9as,11ar)-3a,9a,11a-trimethyl-1-[(2r)-6-methyl-5-methylideneheptan-2-yl]-1h,2h,3h,4h,5h,5ah,6h,7h,8h,9h,10h,11h-cyclopenta[a]phenanthren-7-ol)

3D SDF for NP0178099 ((1r,3ar,5as,7s,9as,11ar)-3a,9a,11a-trimethyl-1-[(2r)-6-methyl-5-methylideneheptan-2-yl]-1h,2h,3h,4h,5h,5ah,6h,7h,8h,9h,10h,11h-cyclopenta[a]phenanthren-7-ol)

3D-SDF for NP0178099 ((1r,3ar,5as,7s,9as,11ar)-3a,9a,11a-trimethyl-1-[(2r)-6-methyl-5-methylideneheptan-2-yl]-1h,2h,3h,4h,5h,5ah,6h,7h,8h,9h,10h,11h-cyclopenta[a]phenanthren-7-ol)

PDB for NP0178099 ((1r,3ar,5as,7s,9as,11ar)-3a,9a,11a-trimethyl-1-[(2r)-6-methyl-5-methylideneheptan-2-yl]-1h,2h,3h,4h,5h,5ah,6h,7h,8h,9h,10h,11h-cyclopenta[a]phenanthren-7-ol)

3D PDB for NP0178099 ((1r,3ar,5as,7s,9as,11ar)-3a,9a,11a-trimethyl-1-[(2r)-6-methyl-5-methylideneheptan-2-yl]-1h,2h,3h,4h,5h,5ah,6h,7h,8h,9h,10h,11h-cyclopenta[a]phenanthren-7-ol)

SMILES for NP0178099 ((1r,3ar,5as,7s,9as,11ar)-3a,9a,11a-trimethyl-1-[(2r)-6-methyl-5-methylideneheptan-2-yl]-1h,2h,3h,4h,5h,5ah,6h,7h,8h,9h,10h,11h-cyclopenta[a]phenanthren-7-ol)

INCHI for NP0178099 ((1r,3ar,5as,7s,9as,11ar)-3a,9a,11a-trimethyl-1-[(2r)-6-methyl-5-methylideneheptan-2-yl]-1h,2h,3h,4h,5h,5ah,6h,7h,8h,9h,10h,11h-cyclopenta[a]phenanthren-7-ol)

Structure for NP0178099 ((1r,3ar,5as,7s,9as,11ar)-3a,9a,11a-trimethyl-1-[(2r)-6-methyl-5-methylideneheptan-2-yl]-1h,2h,3h,4h,5h,5ah,6h,7h,8h,9h,10h,11h-cyclopenta[a]phenanthren-7-ol)

3D Structure for NP0178099 ((1r,3ar,5as,7s,9as,11ar)-3a,9a,11a-trimethyl-1-[(2r)-6-methyl-5-methylideneheptan-2-yl]-1h,2h,3h,4h,5h,5ah,6h,7h,8h,9h,10h,11h-cyclopenta[a]phenanthren-7-ol)