NP-MRD: Showing NP-Card for (24R)-ergosta-8,22-diene-3beta,6beta,7alpha-triol (NP0085644)

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Record Information

Version

2.0

Created at

2022-04-29 06:08:58 UTC

Updated at

2022-04-29 06:08:58 UTC

NP-MRD ID

NP0085644

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(24R)-ergosta-8,22-diene-3beta,6beta,7alpha-triol

Description

(24R)-ergosta-8,22-diene-3beta,6beta,7alpha-triol is found in Ruppia maritima. Based on a literature review very few articles have been published on (2S,5S,7S,8S,9S,11R,14R,15R)-14-[(2R,3E,5R)-5,6-dimethylhept-3-en-2-yl]-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadec-1(10)-ene-5,8,9-triol.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304292208082D          

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M  END

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M  END


  Mrv1652304292208082D          

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 22 23  1  1  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  1  0  0  0
 25 27  1  0  0  0  0
 20 27  1  0  0  0  0
 27 28  1  6  0  0  0
 24 29  1  6  0  0  0
 24 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  1  0  0  0
 31 33  1  0  0  0  0
 33 34  1  0  0  0  0
 22 34  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0085644

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@@]1(CC[C@@]2([H])C3=C(CC[C@]12C)[C@@]1(C)CC[C@H](O)C[C@]1([H])[C@H](O)[C@H]3O)[C@H](C)\C=C\[C@H](C)C(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C28H46O3/c1-16(2)17(3)7-8-18(4)20-9-10-21-24-22(12-14-27(20,21)5)28(6)13-11-19(29)15-23(28)25(30)26(24)31/h7-8,16-21,23,25-26,29-31H,9-15H2,1-6H3/b8-7+/t17-,18+,19-,20+,21-,23+,25-,26-,27+,28+/m0/s1

> <INCHI_KEY>
PCYLGNDEPYKQOL-PZSZHJQASA-N

> <FORMULA>
C28H46O3

> <MOLECULAR_WEIGHT>
430.673

> <EXACT_MASS>
430.344695341

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
77

> <JCHEM_AVERAGE_POLARIZABILITY>
52.37835500382633

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S,5S,7S,8S,9S,11R,14R,15R)-14-[(2R,3E,5R)-5,6-dimethylhept-3-en-2-yl]-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-1(10)-ene-5,8,9-triol

> <ALOGPS_LOGP>
4.64

> <JCHEM_LOGP>
4.766567701666668

> <ALOGPS_LOGS>
-4.56

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.72705684350457

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.400043568476597

> <JCHEM_PKA_STRONGEST_BASIC>
-2.6915390050343317

> <JCHEM_POLAR_SURFACE_AREA>
60.69

> <JCHEM_REFRACTIVITY>
128.81510000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.18e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S,5S,7S,8S,9S,11R,14R,15R)-14-[(2R,3E,5R)-5,6-dimethylhept-3-en-2-yl]-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-1(10)-ene-5,8,9-triol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 29-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-APR-22         0                                  
HETATM    1  H   UNK     0      10.449   1.514   0.000  0.00  0.00           H+0
HETATM    2  C   UNK     0       8.937   1.804   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       9.882   3.020   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.302   4.447   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      11.407   2.809   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      11.988   1.383   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      13.513   1.172   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      14.458   2.388   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      14.094  -0.254   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      15.619  -0.465   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      13.148  -1.470   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       9.365   0.325   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.090  -0.539   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.874   0.406   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.398   1.854   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.069   3.240   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.405   3.032   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.889   2.761   0.000  0.00  0.00           C+0
HETATM   19  H   UNK     0       5.882   1.583   0.000  0.00  0.00           H+0
HETATM   20  C   UNK     0       5.358   0.135   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.366   1.312   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       2.850   1.041   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       3.373   2.489   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       2.326  -0.407   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       3.319  -1.585   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       2.796  -3.033   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       4.835  -1.314   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       5.828  -2.491   0.000  0.00  0.00           O+0
HETATM   29  H   UNK     0       1.803  -1.856   0.000  0.00  0.00           H+0
HETATM   30  C   UNK     0       0.810  -0.678   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -0.182   0.499   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      -1.698   0.228   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       0.341   1.947   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       1.857   2.218   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   12   15                                             
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9                                                            
CONECT   12    2   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   19   20                                             
CONECT   15   14    2   16   17                                             
CONECT   16   15                                                            
CONECT   17   15   18                                                       
CONECT   18   17   21                                                       
CONECT   19   14                                                            
CONECT   20   14   21   27                                                  
CONECT   21   20   18   22                                                  
CONECT   22   21   23   24   34                                             
CONECT   23   22                                                            
CONECT   24   22   25   29   30                                             
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   20   28                                                  
CONECT   28   27                                                            
CONECT   29   24                                                            
CONECT   30   24   31                                                       
CONECT   31   30   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31   34                                                       
CONECT   34   33   22                                                       
MASTER        0    0    0    0    0    0    0    0   34    0   74    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₈H₄₆O₃

Average Mass

430.6730 Da

Monoisotopic Mass

430.34470 Da

IUPAC Name

(2S,5S,7S,8S,9S,11R,14R,15R)-14-[(2R,3E,5R)-5,6-dimethylhept-3-en-2-yl]-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-1(10)-ene-5,8,9-triol

Traditional Name

(2S,5S,7S,8S,9S,11R,14R,15R)-14-[(2R,3E,5R)-5,6-dimethylhept-3-en-2-yl]-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-1(10)-ene-5,8,9-triol

CAS Registry Number

Not Available

SMILES

[H][C@@]1(CC[C@@]2([H])C3=C(CC[C@]12C)[C@@]1(C)CC[C@H](O)C[C@]1([H])[C@H](O)[C@H]3O)[C@H](C)\C=C\[C@H](C)C(C)C

InChI Identifier

InChI=1S/C28H46O3/c1-16(2)17(3)7-8-18(4)20-9-10-21-24-22(12-14-27(20,21)5)28(6)13-11-19(29)15-23(28)25(30)26(24)31/h7-8,16-21,23,25-26,29-31H,9-15H2,1-6H3/b8-7+/t17-,18+,19-,20+,21-,23+,25-,26-,27+,28+/m0/s1

InChI Key

PCYLGNDEPYKQOL-PZSZHJQASA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Ruppia maritima	Plant	KNApSAcK

Chemical Taxonomy

Classification

Not classified

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	4.64	ALOGPS
logP	4.77	ChemAxon
logS	-4.6	ALOGPS
pKa (Strongest Acidic)	13.4	ChemAxon
pKa (Strongest Basic)	-2.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	60.69 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	128.82 m³·mol⁻¹	ChemAxon
Polarizability	52.38 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

C00055576

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

163184086

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for (24R)-ergosta-8,22-diene-3beta,6beta,7alpha-triol (NP0085644)

MOL for NP0085644 ((24R)-ergosta-8,22-diene-3beta,6beta,7alpha-triol)

3D MOL for NP0085644 ((24R)-ergosta-8,22-diene-3beta,6beta,7alpha-triol)

3D SDF for NP0085644 ((24R)-ergosta-8,22-diene-3beta,6beta,7alpha-triol)

3D-SDF for NP0085644 ((24R)-ergosta-8,22-diene-3beta,6beta,7alpha-triol)

PDB for NP0085644 ((24R)-ergosta-8,22-diene-3beta,6beta,7alpha-triol)

3D PDB for NP0085644 ((24R)-ergosta-8,22-diene-3beta,6beta,7alpha-triol)

SMILES for NP0085644 ((24R)-ergosta-8,22-diene-3beta,6beta,7alpha-triol)

INCHI for NP0085644 ((24R)-ergosta-8,22-diene-3beta,6beta,7alpha-triol)

Structure for NP0085644 ((24R)-ergosta-8,22-diene-3beta,6beta,7alpha-triol)

3D Structure for NP0085644 ((24R)-ergosta-8,22-diene-3beta,6beta,7alpha-triol)