NP-MRD: Showing NP-Card for (2s,6r)-6-[(1r,3as,3bs,5r,5ar,7s,9ar,9bs,11ar)-5,5a,7-trihydroxy-9a,11a-dimethyl-tetradecahydrocyclopenta[a]phenanthren-1-yl]-2-methyl-3-methylideneheptyl acetate (NP0232027)

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Record Information

Version

2.0

Created at

2022-09-06 13:07:13 UTC

Updated at

2022-09-06 13:07:13 UTC

NP-MRD ID

NP0232027

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2s,6r)-6-[(1r,3as,3bs,5r,5ar,7s,9ar,9bs,11ar)-5,5a,7-trihydroxy-9a,11a-dimethyl-tetradecahydrocyclopenta[a]phenanthren-1-yl]-2-methyl-3-methylideneheptyl acetate

Description

(25S)-24-Methylenecholestane-3beta,5alpha,6beta,26-tetraol 26-acetate belongs to the class of organic compounds known as trihydroxy bile acids, alcohols and derivatives. These are prenol lipids structurally characterized by a bile acid or alcohol which bears three hydroxyl groups. (2s,6r)-6-[(1r,3as,3bs,5r,5ar,7s,9ar,9bs,11ar)-5,5a,7-trihydroxy-9a,11a-dimethyl-tetradecahydrocyclopenta[a]phenanthren-1-yl]-2-methyl-3-methylideneheptyl acetate is found in Clavularia viridis. Based on a literature review very few articles have been published on (25S)-24-Methylenecholestane-3beta,5alpha,6beta,26-tetraol 26-acetate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309062215072D          

 35 38  0  0  1  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652309062215072D          

 35 38  0  0  1  0            999 V2000
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    2.2999   -0.9394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1069   -1.1109    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3618   -1.8955    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.9749   -1.3435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6879   -1.8186    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.6879   -0.9936    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4023   -2.2311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1168   -1.8186    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.8313   -2.2311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5458   -1.8186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8313   -3.0561    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  6  0  0  0
  7  5  1  1  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
 10  9  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  1  0  0  0
 13 15  1  0  0  0  0
 15 16  1  6  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  1  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 15 22  1  0  0  0  0
 22 23  1  1  0  0  0
 22 24  1  0  0  0  0
 11 24  1  0  0  0  0
 24 25  1  1  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 10 27  1  0  0  0  0
  7 27  1  0  0  0  0
 27 28  1  1  0  0  0
  2 29  1  0  0  0  0
 29 30  1  6  0  0  0
 29 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 33 35  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0232027

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C30H50O5/c1-18(20(3)17-35-21(4)31)7-8-19(2)24-9-10-25-23-15-27(33)30(34)16-22(32)11-14-29(30,6)26(23)12-13-28(24,25)5/h19-20,22-27,32-34H,1,7-17H2,2-6H3/t19-,20-,22+,23+,24-,25+,26+,27-,28-,29-,30+/m1/s1

> <INCHI_KEY>
LVPGFMKWMFAKAI-PTUTYXJZSA-N

> <FORMULA>
C30H50O5

> <MOLECULAR_WEIGHT>
490.725

> <EXACT_MASS>
490.36582471

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
85

> <JCHEM_AVERAGE_POLARIZABILITY>
58.46043153940693

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S,6R)-2-methyl-3-methylidene-6-[(1S,2R,5S,7R,8R,10S,11S,14R,15R)-5,7,8-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]heptyl acetate

> <JCHEM_LOGP>
4.233244943

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.715005071511069

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.287487904702036

> <JCHEM_PKA_STRONGEST_BASIC>
-2.728020209621212

> <JCHEM_POLAR_SURFACE_AREA>
86.99000000000001

> <JCHEM_REFRACTIVITY>
137.9418

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(2S,6R)-2-methyl-3-methylidene-6-[(1S,2R,5S,7R,8R,10S,11S,14R,15R)-5,7,8-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]heptyl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-SEP-22         0                                  
HETATM    1  C   UNK     0      13.017  -5.705   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      13.017  -4.165   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      11.683  -3.395   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      10.350  -4.165   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       9.016  -3.395   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.016  -1.855   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.682  -4.165   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.521  -5.696   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.015  -6.016   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.245  -4.683   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.739  -4.363   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.708  -5.507   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.202  -5.187   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       0.171  -6.331   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       0.726  -3.722   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -0.305  -4.867   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      -0.780  -3.402   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -1.256  -1.937   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -2.763  -1.617   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      -0.226  -0.793   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       1.281  -1.113   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       1.756  -2.578   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       2.787  -1.433   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       3.263  -2.898   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       4.293  -1.754   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       5.800  -2.074   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       6.275  -3.538   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       7.420  -2.508   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      14.351  -3.395   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      14.351  -1.855   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      15.684  -4.165   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      17.018  -3.395   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0      18.352  -4.165   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      19.685  -3.395   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0      18.352  -5.705   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   29                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8   27                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   27                                                  
CONECT   11   10   12   24                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16   17   22                                             
CONECT   16   15                                                            
CONECT   17   15   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   15   23   24                                             
CONECT   23   22                                                            
CONECT   24   22   11   25                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   10    7   28                                             
CONECT   28   27                                                            
CONECT   29    2   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33                                                            
MASTER        0    0    0    0    0    0    0    0   35    0   76    0
END

View in JSmol

Synonyms

Value	Source
(25S)-24-Methylenecholestane-3b,5a,6b,26-tetraol 26-acetate	Generator
(25S)-24-Methylenecholestane-3b,5a,6b,26-tetraol 26-acetic acid	Generator
(25S)-24-Methylenecholestane-3beta,5alpha,6beta,26-tetraol 26-acetic acid	Generator
(25S)-24-Methylenecholestane-3β,5α,6β,26-tetraol 26-acetate	Generator
(25S)-24-Methylenecholestane-3β,5α,6β,26-tetraol 26-acetic acid	Generator

Chemical Formula

C₃₀H₅₀O₅

Average Mass

490.7250 Da

Monoisotopic Mass

490.36582 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

C[C@H](CCC(=C)[C@H](C)COC(C)=O)[C@H]1CC[C@H]2[C@@H]3C[C@@H](O)[C@@]4(O)C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@]12C

InChI Identifier

InChI=1S/C30H50O5/c1-18(20(3)17-35-21(4)31)7-8-19(2)24-9-10-25-23-15-27(33)30(34)16-22(32)11-14-29(30,6)26(23)12-13-28(24,25)5/h19-20,22-27,32-34H,1,7-17H2,2-6H3/t19-,20-,22+,23+,24-,25+,26+,27-,28-,29-,30+/m1/s1

InChI Key

LVPGFMKWMFAKAI-PTUTYXJZSA-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
Clavularia viridis	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as trihydroxy bile acids, alcohols and derivatives. These are prenol lipids structurally characterized by a bile acid or alcohol which bears three hydroxyl groups.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Bile acids, alcohols and derivatives

Direct Parent

Trihydroxy bile acids, alcohols and derivatives

Alternative Parents

Substituents

Ergosterol-skeleton
Ergostane-skeleton
Trihydroxy bile acid, alcohol, or derivatives
Steroid ester
3-hydroxysteroid
3-beta-hydroxysteroid
6-hydroxysteroid
5-hydroxysteroid
Hydroxysteroid
Cyclic alcohol
Tertiary alcohol
Carboxylic acid ester
Secondary alcohol
Polyol
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Alcohol
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Carbonyl group
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

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

27023739

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

24865197

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2s,6r)-6-[(1r,3as,3bs,5r,5ar,7s,9ar,9bs,11ar)-5,5a,7-trihydroxy-9a,11a-dimethyl-tetradecahydrocyclopenta[a]phenanthren-1-yl]-2-methyl-3-methylideneheptyl acetate (NP0232027)

MOL for NP0232027 ((2s,6r)-6-[(1r,3as,3bs,5r,5ar,7s,9ar,9bs,11ar)-5,5a,7-trihydroxy-9a,11a-dimethyl-tetradecahydrocyclopenta[a]phenanthren-1-yl]-2-methyl-3-methylideneheptyl acetate)

3D MOL for NP0232027 ((2s,6r)-6-[(1r,3as,3bs,5r,5ar,7s,9ar,9bs,11ar)-5,5a,7-trihydroxy-9a,11a-dimethyl-tetradecahydrocyclopenta[a]phenanthren-1-yl]-2-methyl-3-methylideneheptyl acetate)

3D SDF for NP0232027 ((2s,6r)-6-[(1r,3as,3bs,5r,5ar,7s,9ar,9bs,11ar)-5,5a,7-trihydroxy-9a,11a-dimethyl-tetradecahydrocyclopenta[a]phenanthren-1-yl]-2-methyl-3-methylideneheptyl acetate)

3D-SDF for NP0232027 ((2s,6r)-6-[(1r,3as,3bs,5r,5ar,7s,9ar,9bs,11ar)-5,5a,7-trihydroxy-9a,11a-dimethyl-tetradecahydrocyclopenta[a]phenanthren-1-yl]-2-methyl-3-methylideneheptyl acetate)

PDB for NP0232027 ((2s,6r)-6-[(1r,3as,3bs,5r,5ar,7s,9ar,9bs,11ar)-5,5a,7-trihydroxy-9a,11a-dimethyl-tetradecahydrocyclopenta[a]phenanthren-1-yl]-2-methyl-3-methylideneheptyl acetate)

3D PDB for NP0232027 ((2s,6r)-6-[(1r,3as,3bs,5r,5ar,7s,9ar,9bs,11ar)-5,5a,7-trihydroxy-9a,11a-dimethyl-tetradecahydrocyclopenta[a]phenanthren-1-yl]-2-methyl-3-methylideneheptyl acetate)

SMILES for NP0232027 ((2s,6r)-6-[(1r,3as,3bs,5r,5ar,7s,9ar,9bs,11ar)-5,5a,7-trihydroxy-9a,11a-dimethyl-tetradecahydrocyclopenta[a]phenanthren-1-yl]-2-methyl-3-methylideneheptyl acetate)

INCHI for NP0232027 ((2s,6r)-6-[(1r,3as,3bs,5r,5ar,7s,9ar,9bs,11ar)-5,5a,7-trihydroxy-9a,11a-dimethyl-tetradecahydrocyclopenta[a]phenanthren-1-yl]-2-methyl-3-methylideneheptyl acetate)

Structure for NP0232027 ((2s,6r)-6-[(1r,3as,3bs,5r,5ar,7s,9ar,9bs,11ar)-5,5a,7-trihydroxy-9a,11a-dimethyl-tetradecahydrocyclopenta[a]phenanthren-1-yl]-2-methyl-3-methylideneheptyl acetate)

3D Structure for NP0232027 ((2s,6r)-6-[(1r,3as,3bs,5r,5ar,7s,9ar,9bs,11ar)-5,5a,7-trihydroxy-9a,11a-dimethyl-tetradecahydrocyclopenta[a]phenanthren-1-yl]-2-methyl-3-methylideneheptyl acetate)