NP-MRD: Showing NP-Card for (+)-Hippuristerol E (NP0078494)

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Record Information

Version

2.0

Created at

2022-04-28 23:34:05 UTC

Updated at

2022-04-28 23:34:05 UTC

NP-MRD ID

NP0078494

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(+)-Hippuristerol E

Description

(1R,2S,3S)-4-hydroxy-1-[(1'S,2S,2'S,3S,5'R,7'S,10'R,11'S,15'S)-5'-hydroxy-2',3,15'-trimethylspiro[oxirane-2,14'-tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadecane]-3-yl]-2,3,4-trimethylpentyl acetate 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. (+)-Hippuristerol E is found in Isis hippuris. Based on a literature review very few articles have been published on (1R,2S,3S)-4-hydroxy-1-[(1'S,2S,2'S,3S,5'R,7'S,10'R,11'S,15'S)-5'-hydroxy-2',3,15'-trimethylspiro[oxirane-2,14'-tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadecane]-3-yl]-2,3,4-trimethylpentyl acetate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304292201342D          

 36 40  0  0  1  0            999 V2000
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M  END

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M  END


  Mrv1652304292201342D          

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    7.2692    0.4276    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7947   -0.2473    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.0909    0.3541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4222    0.3595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5193   -0.1298    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3165    1.8951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4919    1.8679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1032    1.1402    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5390    0.4397    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1503   -0.2880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3258   -0.3152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1101    0.3853    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2786    1.1130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9346    0.3581    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9749   -0.2608    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6  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  0  0  0  0
  1  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  4  9  1  6  0  0  0
  7 10  1  0  0  0  0
 10 11  1  0  0  0  0
  7 11  1  6  0  0  0
 10 12  1  6  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  1  0  0  0  0
 15 18  1  0  0  0  0
 14 19  1  1  0  0  0
 13 20  1  1  0  0  0
 12 21  1  1  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
 10 25  1  1  0  0  0
  5 26  1  6  0  0  0
  3 27  1  1  0  0  0
 27 28  1  0  0  0  0
 29 28  1  6  0  0  0
 29 30  1  0  0  0  0
  2 30  1  0  0  0  0
 30 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
 29 34  1  0  0  0  0
 33 35  1  1  0  0  0
 30 36  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0078494

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H]([C@H](C)C(C)(C)O)[C@@H](OC(C)=O)[C@]1(C)O[C@]11CC[C@H]2[C@@H]3CC[C@H]4C[C@H](O)CC[C@]4(C)[C@H]3CC[C@]12C

> <INCHI_IDENTIFIER>
InChI=1S/C31H52O5/c1-18(19(2)27(4,5)34)26(35-20(3)32)30(8)31(36-30)16-13-25-23-10-9-21-17-22(33)11-14-28(21,6)24(23)12-15-29(25,31)7/h18-19,21-26,33-34H,9-17H2,1-8H3/t18-,19-,21-,22+,23+,24-,25-,26+,28-,29-,30-,31-/m0/s1

> <INCHI_KEY>
MCEICBGPGATZRB-GZNXOJKZSA-N

> <FORMULA>
C31H52O5

> <MOLECULAR_WEIGHT>
504.752

> <EXACT_MASS>
504.381474774

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
88

> <JCHEM_AVERAGE_POLARIZABILITY>
59.784404734273565

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,2S,3S)-4-hydroxy-1-[(1'S,2S,2'S,3S,5'R,7'S,10'R,11'S,15'S)-5'-hydroxy-2',3,15'-trimethylspiro[oxirane-2,14'-tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecane]-3-yl]-2,3,4-trimethylpentyl acetate

> <ALOGPS_LOGP>
5.19

> <JCHEM_LOGP>
5.0645790553333345

> <ALOGPS_LOGS>
-6.34

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
18.2963963211217

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.064712837580899

> <JCHEM_PKA_STRONGEST_BASIC>
-1.356426975499549

> <JCHEM_POLAR_SURFACE_AREA>
79.28999999999999

> <JCHEM_REFRACTIVITY>
140.5279

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.30e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2S,3S)-4-hydroxy-1-[(1'S,2S,2'S,3S,5'R,7'S,10'R,11'S,15'S)-5'-hydroxy-2',3,15'-trimethylspiro[oxirane-2,14'-tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecane]-3-yl]-2,3,4-trimethylpentyl acetate

> <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  C   UNK     0       5.226  -0.436   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.412   0.872   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.138   2.230   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.677   2.281   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.490   0.973   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.765  -0.385   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.985   1.343   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.096   2.879   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.669   3.459   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      10.501   1.072   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       9.509  -0.105   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      11.387   2.332   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      10.739   3.729   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      11.625   4.989   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      10.977   6.386   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      10.328   7.783   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       9.580   5.738   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      12.374   7.034   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      13.159   4.852   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       9.205   3.866   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      12.921   2.195   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      13.569   0.798   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      12.683  -0.462   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      15.103   0.661   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      11.988   0.671   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       8.436  -0.242   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       4.324   3.537   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       2.785   3.487   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       2.059   2.128   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       2.873   0.821   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       2.147  -0.538   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       0.608  -0.588   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -0.205   0.719   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       0.520   2.078   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0      -1.745   0.668   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0       3.686  -0.487   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    3   30                                                  
CONECT    3    2    4   27                                                  
CONECT    4    3    5    9                                                  
CONECT    5    4    6    7   26                                             
CONECT    6    5    1                                                       
CONECT    7    5    8   10   11                                             
CONECT    8    7    9                                                       
CONECT    9    8    4                                                       
CONECT   10    7   11   12   25                                             
CONECT   11   10    7                                                       
CONECT   12   10   13   21                                                  
CONECT   13   12   14   20                                                  
CONECT   14   13   15   19                                                  
CONECT   15   14   16   17   18                                             
CONECT   16   15                                                            
CONECT   17   15                                                            
CONECT   18   15                                                            
CONECT   19   14                                                            
CONECT   20   13                                                            
CONECT   21   12   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22                                                            
CONECT   25   10                                                            
CONECT   26    5                                                            
CONECT   27    3   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30   34                                                  
CONECT   30   29    2   31   36                                             
CONECT   31   30   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   34   35                                                  
CONECT   34   33   29                                                       
CONECT   35   33                                                            
CONECT   36   30                                                            
MASTER        0    0    0    0    0    0    0    0   36    0   80    0
END

View in JSmol

Synonyms

Value	Source
(1R,2S,3S)-4-Hydroxy-1-[(1's,2S,2's,3S,5'r,7's,10'r,11's,15's)-5'-hydroxy-2',3,15'-trimethylspiro[oxirane-2,14'-tetracyclo[8.7.0.0,.0,]heptadecane]-3-yl]-2,3,4-trimethylpentyl acetic acid	Generator

Chemical Formula

C₃₁H₅₂O₅

Average Mass

504.7520 Da

Monoisotopic Mass

504.38147 Da

IUPAC Name

(1R,2S,3S)-4-hydroxy-1-[(1'S,2S,2'S,3S,5'R,7'S,10'R,11'S,15'S)-5'-hydroxy-2',3,15'-trimethylspiro[oxirane-2,14'-tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecane]-3-yl]-2,3,4-trimethylpentyl acetate

Traditional Name

(1R,2S,3S)-4-hydroxy-1-[(1'S,2S,2'S,3S,5'R,7'S,10'R,11'S,15'S)-5'-hydroxy-2',3,15'-trimethylspiro[oxirane-2,14'-tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecane]-3-yl]-2,3,4-trimethylpentyl acetate

CAS Registry Number

Not Available

SMILES

C[C@@H]([C@H](C)C(C)(C)O)[C@@H](OC(C)=O)[C@]1(C)O[C@]11CC[C@H]2[C@@H]3CC[C@H]4C[C@H](O)CC[C@]4(C)[C@H]3CC[C@]12C

InChI Identifier

InChI=1S/C31H52O5/c1-18(19(2)27(4,5)34)26(35-20(3)32)30(8)31(36-30)16-13-25-23-10-9-21-17-22(33)11-14-28(21,6)24(23)12-15-29(25,31)7/h18-19,21-26,33-34H,9-17H2,1-8H3/t18-,19-,21-,22+,23+,24-,25-,26+,28-,29-,30-,31-/m0/s1

InChI Key

MCEICBGPGATZRB-GZNXOJKZSA-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
Isis hippuris	-	KNApSAcK

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
3-alpha-hydroxysteroid
Tertiary alcohol
Cyclic alcohol
Secondary alcohol
Carboxylic acid ester
Organoheterocyclic compound
Oxacycle
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Ether
Oxirane
Dialkyl ether
Organic oxide
Organic oxygen compound
Alcohol
Organooxygen compound
Carbonyl group
Hydrocarbon derivative
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic 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	5.19	ALOGPS
logP	5.06	ChemAxon
logS	-6.3	ALOGPS
pKa (Strongest Acidic)	15.06	ChemAxon
pKa (Strongest Basic)	-1.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	79.29 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	140.53 m³·mol⁻¹	ChemAxon
Polarizability	59.78 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	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

9744443

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11569673

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for (+)-Hippuristerol E (NP0078494)

MOL for NP0078494 ((+)-Hippuristerol E)

3D MOL for NP0078494 ((+)-Hippuristerol E)

3D SDF for NP0078494 ((+)-Hippuristerol E)

3D-SDF for NP0078494 ((+)-Hippuristerol E)

PDB for NP0078494 ((+)-Hippuristerol E)

3D PDB for NP0078494 ((+)-Hippuristerol E)

SMILES for NP0078494 ((+)-Hippuristerol E)

INCHI for NP0078494 ((+)-Hippuristerol E)

Structure for NP0078494 ((+)-Hippuristerol E)

3D Structure for NP0078494 ((+)-Hippuristerol E)