NP-MRD: Showing NP-Card for (3s,4e,6r)-6-[(1r,3s,3as,3br,5r,5ar,7s,9ar,9bs,11ar)-3,5,5a,7-tetrahydroxy-9a,11a-dimethyl-tetradecahydrocyclopenta[a]phenanthren-1-yl]-3-methylhept-4-enoic acid (NP0182776)

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Record Information

Version

2.0

Created at

2022-09-03 21:34:05 UTC

Updated at

2022-09-03 21:34:05 UTC

NP-MRD ID

NP0182776

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(3s,4e,6r)-6-[(1r,3s,3as,3br,5r,5ar,7s,9ar,9bs,11ar)-3,5,5a,7-tetrahydroxy-9a,11a-dimethyl-tetradecahydrocyclopenta[a]phenanthren-1-yl]-3-methylhept-4-enoic acid

Description

(3S,4E,6R)-3-methyl-6-[(1S,2R,5S,7R,8R,10R,11S,12S,14R,15R)-5,7,8,12-tetrahydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadecan-14-yl]hept-4-enoic acid belongs to the class of organic compounds known as 3-beta-hydroxysteroids. These are steroids carrying a beta-hydroxyl group at the 3-position of the steroid backbone. (3s,4e,6r)-6-[(1r,3s,3as,3br,5r,5ar,7s,9ar,9bs,11ar)-3,5,5a,7-tetrahydroxy-9a,11a-dimethyl-tetradecahydrocyclopenta[a]phenanthren-1-yl]-3-methylhept-4-enoic acid is found in Myxoderma platyacanthum. Based on a literature review very few articles have been published on (3S,4E,6R)-3-methyl-6-[(1S,2R,5S,7R,8R,10R,11S,12S,14R,15R)-5,7,8,12-tetrahydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadecan-14-yl]hept-4-enoic acid.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309032223342D          

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M  END

     RDKit          3D

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M  END


  Mrv1652309032223342D          

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  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  1  0  0  0
  7  5  1  1  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  6  0  0  0
 11  9  1  1  0  0  0
 11 12  1  0  0  0  0
 12 13  1  6  0  0  0
 13 14  1  0  0  0  0
 14 15  1  1  0  0  0
 14 16  1  0  0  0  0
 16 17  1  6  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  1  0  0  0
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 16 23  1  0  0  0  0
 23 24  1  1  0  0  0
 23 25  1  0  0  0  0
 12 25  1  0  0  0  0
 25 26  1  1  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 11 28  1  0  0  0  0
  7 28  1  0  0  0  0
 28 29  1  1  0  0  0
  2 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  2  0  0  0  0
 31 33  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0182776

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H](CC(O)=O)\C=C\[C@@H](C)[C@H]1C[C@H](O)[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/C27H44O6/c1-15(11-23(31)32)5-6-16(2)20-13-21(29)24-18-12-22(30)27(33)14-17(28)7-10-26(27,4)19(18)8-9-25(20,24)3/h5-6,15-22,24,28-30,33H,7-14H2,1-4H3,(H,31,32)/b6-5+/t15-,16-,17+,18-,19+,20-,21+,22-,24-,25-,26-,27+/m1/s1

> <INCHI_KEY>
BCOCYZFBZDJHOV-YUKSPCHPSA-N

> <FORMULA>
C27H44O6

> <MOLECULAR_WEIGHT>
464.643

> <EXACT_MASS>
464.313789137

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
77

> <JCHEM_AVERAGE_POLARIZABILITY>
52.845425546855026

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(3S,4E,6R)-3-methyl-6-[(1S,2R,5S,7R,8R,10R,11S,12S,14R,15R)-5,7,8,12-tetrahydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]hept-4-enoic acid

> <JCHEM_LOGP>
2.2205429153333323

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
13.287457530588917

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.616651264919317

> <JCHEM_PKA_STRONGEST_BASIC>
-0.649000573233859

> <JCHEM_POLAR_SURFACE_AREA>
118.22000000000001

> <JCHEM_REFRACTIVITY>
126.98699999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(3S,4E,6R)-3-methyl-6-[(1S,2R,5S,7R,8R,10R,11S,12S,14R,15R)-5,7,8,12-tetrahydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]hept-4-enoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

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       4.053 -11.147   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.998  -9.932   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.417  -8.505   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.363  -7.289   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.782  -5.863   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.257  -5.652   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.727  -4.647   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.299  -3.168   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.574  -2.304   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       6.624  -0.764   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       7.790  -3.249   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       9.306  -2.978   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       9.829  -1.529   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      11.345  -1.258   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      11.868   0.190   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      12.338  -2.436   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      12.861  -0.987   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      13.854  -2.164   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      14.846  -3.342   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      16.362  -3.071   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      14.323  -4.790   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      12.807  -5.061   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      11.814  -3.884   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      11.291  -5.332   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      10.299  -4.155   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       9.775  -5.603   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       8.259  -5.874   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       7.267  -4.697   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       6.595  -6.083   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       6.523 -10.142   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       7.104 -11.569   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       8.629 -11.779   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0       6.158 -12.785   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   30                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8   28                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   28                                                  
CONECT   12   11   13   25                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17   18   23                                             
CONECT   17   16                                                            
CONECT   18   16   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   16   24   25                                             
CONECT   24   23                                                            
CONECT   25   23   12   26                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   11    7   29                                             
CONECT   29   28                                                            
CONECT   30    2   31                                                       
CONECT   31   30   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   72    0
END

View in JSmol

Synonyms

Value	Source
(3S,4E,6R)-3-Methyl-6-[(1S,2R,5S,7R,8R,10R,11S,12S,14R,15R)-5,7,8,12-tetrahydroxy-2,15-dimethyltetracyclo[8.7.0.0,.0,]heptadecan-14-yl]hept-4-enoate	Generator

Chemical Formula

C₂₇H₄₄O₆

Average Mass

464.6430 Da

Monoisotopic Mass

464.31379 Da

IUPAC Name

(3S,4E,6R)-3-methyl-6-[(1S,2R,5S,7R,8R,10R,11S,12S,14R,15R)-5,7,8,12-tetrahydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]hept-4-enoic acid

Traditional Name

(3S,4E,6R)-3-methyl-6-[(1S,2R,5S,7R,8R,10R,11S,12S,14R,15R)-5,7,8,12-tetrahydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]hept-4-enoic acid

CAS Registry Number

Not Available

SMILES

C[C@@H](CC(O)=O)\C=C\[C@@H](C)[C@H]1C[C@H](O)[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/C27H44O6/c1-15(11-23(31)32)5-6-16(2)20-13-21(29)24-18-12-22(30)27(33)14-17(28)7-10-26(27,4)19(18)8-9-25(20,24)3/h5-6,15-22,24,28-30,33H,7-14H2,1-4H3,(H,31,32)/b6-5+/t15-,16-,17+,18-,19+,20-,21+,22-,24-,25-,26-,27+/m1/s1

InChI Key

BCOCYZFBZDJHOV-YUKSPCHPSA-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
Myxoderma platyacanthum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 3-beta-hydroxysteroids. These are steroids carrying a beta-hydroxyl group at the 3-position of the steroid backbone.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Hydroxysteroids

Direct Parent

3-beta-hydroxysteroids

Alternative Parents

Substituents

Steroid acid
6-hydroxysteroid
3-beta-hydroxysteroid
Medium-chain fatty acid
Branched fatty acid
Hydroxy fatty acid
Methyl-branched fatty acid
Fatty acyl
Fatty acid
Unsaturated fatty acid
Cyclic alcohol
Tertiary alcohol
Secondary alcohol
Polyol
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Alcohol
Carbonyl group
Organic oxygen 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
logP	2.22	ChemAxon
pKa (Strongest Acidic)	4.62	ChemAxon
pKa (Strongest Basic)	-0.65	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	118.22 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	126.99 m³·mol⁻¹	ChemAxon
Polarizability	52.85 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	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

10267273

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

21634650

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (3s,4e,6r)-6-[(1r,3s,3as,3br,5r,5ar,7s,9ar,9bs,11ar)-3,5,5a,7-tetrahydroxy-9a,11a-dimethyl-tetradecahydrocyclopenta[a]phenanthren-1-yl]-3-methylhept-4-enoic acid (NP0182776)

MOL for NP0182776 ((3s,4e,6r)-6-[(1r,3s,3as,3br,5r,5ar,7s,9ar,9bs,11ar)-3,5,5a,7-tetrahydroxy-9a,11a-dimethyl-tetradecahydrocyclopenta[a]phenanthren-1-yl]-3-methylhept-4-enoic acid)

3D MOL for NP0182776 ((3s,4e,6r)-6-[(1r,3s,3as,3br,5r,5ar,7s,9ar,9bs,11ar)-3,5,5a,7-tetrahydroxy-9a,11a-dimethyl-tetradecahydrocyclopenta[a]phenanthren-1-yl]-3-methylhept-4-enoic acid)

3D SDF for NP0182776 ((3s,4e,6r)-6-[(1r,3s,3as,3br,5r,5ar,7s,9ar,9bs,11ar)-3,5,5a,7-tetrahydroxy-9a,11a-dimethyl-tetradecahydrocyclopenta[a]phenanthren-1-yl]-3-methylhept-4-enoic acid)

3D-SDF for NP0182776 ((3s,4e,6r)-6-[(1r,3s,3as,3br,5r,5ar,7s,9ar,9bs,11ar)-3,5,5a,7-tetrahydroxy-9a,11a-dimethyl-tetradecahydrocyclopenta[a]phenanthren-1-yl]-3-methylhept-4-enoic acid)

PDB for NP0182776 ((3s,4e,6r)-6-[(1r,3s,3as,3br,5r,5ar,7s,9ar,9bs,11ar)-3,5,5a,7-tetrahydroxy-9a,11a-dimethyl-tetradecahydrocyclopenta[a]phenanthren-1-yl]-3-methylhept-4-enoic acid)

3D PDB for NP0182776 ((3s,4e,6r)-6-[(1r,3s,3as,3br,5r,5ar,7s,9ar,9bs,11ar)-3,5,5a,7-tetrahydroxy-9a,11a-dimethyl-tetradecahydrocyclopenta[a]phenanthren-1-yl]-3-methylhept-4-enoic acid)

SMILES for NP0182776 ((3s,4e,6r)-6-[(1r,3s,3as,3br,5r,5ar,7s,9ar,9bs,11ar)-3,5,5a,7-tetrahydroxy-9a,11a-dimethyl-tetradecahydrocyclopenta[a]phenanthren-1-yl]-3-methylhept-4-enoic acid)

INCHI for NP0182776 ((3s,4e,6r)-6-[(1r,3s,3as,3br,5r,5ar,7s,9ar,9bs,11ar)-3,5,5a,7-tetrahydroxy-9a,11a-dimethyl-tetradecahydrocyclopenta[a]phenanthren-1-yl]-3-methylhept-4-enoic acid)

Structure for NP0182776 ((3s,4e,6r)-6-[(1r,3s,3as,3br,5r,5ar,7s,9ar,9bs,11ar)-3,5,5a,7-tetrahydroxy-9a,11a-dimethyl-tetradecahydrocyclopenta[a]phenanthren-1-yl]-3-methylhept-4-enoic acid)

3D Structure for NP0182776 ((3s,4e,6r)-6-[(1r,3s,3as,3br,5r,5ar,7s,9ar,9bs,11ar)-3,5,5a,7-tetrahydroxy-9a,11a-dimethyl-tetradecahydrocyclopenta[a]phenanthren-1-yl]-3-methylhept-4-enoic acid)