NP-MRD: Showing NP-Card for 3-Epiglochidiol (NP0137676)

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Record Information

Version

1.0

Created at

2022-05-31 16:03:01 UTC

Updated at

2022-05-31 16:03:01 UTC

NP-MRD ID

NP0137676

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3-Epiglochidiol

Description

20(29)-Lupene-1beta,3beta-diol, also known as 3-epi-glochidiol, belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units. 3-Epiglochidiol is found in Breynia fruticosa, Celastrus hypoleucus, Glochidion eriocarpum, Glochidion puberum, Glochidion zeylanicum and Salvia deserta. It was first documented in 2006 (PMID: 16455245). Based on a literature review very few articles have been published on 20(29)-lupene-1beta,3beta-diol (PMID: 21428418).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652305312218032D          

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M  END

     RDKit          3D

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M  END


  Mrv1652305312218032D          

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   10.9263   -2.7581    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.3279   -2.0374    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.1014   -2.7706    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2765   -2.7832    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    9.6998   -3.4913    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.8749   -3.5038    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.8532   -2.0750    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.4516   -2.7957    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5536   -2.1252    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.9551   -1.4046    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1947   -3.5509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9831   -3.7939    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5901   -4.1122    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1  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  1  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  6  0  0  0
  9 11  1  0  0  0  0
 11 12  1  1  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  6  0  0  0
 15 17  1  0  0  0  0
  9 17  1  0  0  0  0
 17 18  1  1  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  6  0  0  0
 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
 23 25  1  0  0  0  0
 23 26  1  0  0  0  0
 26 27  1  6  0  0  0
 26 28  1  1  0  0  0
 26 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  6  0  0  0
 30 32  1  1  0  0  0
 30 33  1  0  0  0  0
 15 33  1  0  0  0  0
 21 33  1  0  0  0  0
 33 34  1  1  0  0  0
 11 35  1  0  0  0  0
  2 35  1  0  0  0  0
  5 35  1  0  0  0  0
 35 36  1  6  0  0  0
  2 37  1  6  0  0  0
 37 38  1  0  0  0  0
 37 39  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0137676

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@]1(CC[C@]2(C)CC[C@]3(C)[C@]([H])(CC[C@@]4([H])[C@@]3(C)CC[C@@]3([H])C(C)(C)[C@@]([H])(O)C[C@@]([H])(O)[C@]43C)[C@@]12[H])C(C)=C

> <INCHI_IDENTIFIER>
InChI=1S/C30H50O2/c1-18(2)19-11-13-27(5)15-16-28(6)20(25(19)27)9-10-22-29(28,7)14-12-21-26(3,4)23(31)17-24(32)30(21,22)8/h19-25,31-32H,1,9-17H2,2-8H3/t19-,20+,21-,22-,23-,24+,25+,27+,28+,29+,30-/m0/s1

> <INCHI_KEY>
SWEUJTWPRYKNNX-AXLUDCLJSA-N

> <FORMULA>
C30H50O2

> <MOLECULAR_WEIGHT>
442.728

> <EXACT_MASS>
442.38108085

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
82

> <JCHEM_AVERAGE_POLARIZABILITY>
54.4830385119252

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,2R,5R,8R,9R,10R,13S,14R,15R,17S,19S)-1,2,5,14,18,18-hexamethyl-8-(prop-1-en-2-yl)pentacyclo[11.8.0.0^{2,10}.0^{5,9}.0^{14,19}]henicosane-15,17-diol

> <JCHEM_LOGP>
6.144441408000001

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.019212641057546

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.316028225604082

> <JCHEM_PKA_STRONGEST_BASIC>
-2.962357883617428

> <JCHEM_POLAR_SURFACE_AREA>
40.46

> <JCHEM_REFRACTIVITY>
132.38019999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2R,5R,8R,9R,10R,13S,14R,15R,17S,19S)-1,2,5,14,18,18-hexamethyl-8-(prop-1-en-2-yl)pentacyclo[11.8.0.0^{2,10}.0^{5,9}.0^{14,19}]henicosane-15,17-diol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 31-MAY-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   31-MAY-22         0                                  
HETATM    1  H   UNK     0      10.847  -5.503   0.000  0.00  0.00           H+0
HETATM    2  C   UNK     0       9.354  -5.127   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.937  -4.522   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.075  -2.988   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       9.576  -2.645   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.652  -1.413   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      10.326  -1.300   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      11.866  -1.277   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      12.656  -2.598   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      13.406  -1.253   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      11.906  -3.944   0.000  0.00  0.00           C+0
HETATM   12  H   UNK     0      11.157  -5.289   0.000  0.00  0.00           H+0
HETATM   13  C   UNK     0      12.697  -5.265   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      14.236  -5.242   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      14.986  -3.897   0.000  0.00  0.00           C+0
HETATM   16  H   UNK     0      15.736  -2.552   0.000  0.00  0.00           H+0
HETATM   17  C   UNK     0      14.196  -2.575   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      14.334  -1.041   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      14.946  -1.230   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      16.485  -1.206   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      17.276  -2.528   0.000  0.00  0.00           C+0
HETATM   22  H   UNK     0      18.066  -3.850   0.000  0.00  0.00           H+0
HETATM   23  C   UNK     0      18.815  -2.505   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      18.525  -0.992   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      20.254  -1.956   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      19.606  -3.827   0.000  0.00  0.00           C+0
HETATM   27  H   UNK     0      20.396  -5.148   0.000  0.00  0.00           H+0
HETATM   28  O   UNK     0      21.145  -3.803   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      18.856  -5.172   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      17.316  -5.195   0.000  0.00  0.00           C+0
HETATM   31  H   UNK     0      18.106  -6.517   0.000  0.00  0.00           H+0
HETATM   32  O   UNK     0      16.566  -6.540   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0      16.526  -3.873   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      15.776  -5.219   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      10.367  -3.967   0.000  0.00  0.00           C+0
HETATM   36  H   UNK     0      11.116  -2.622   0.000  0.00  0.00           H+0
HETATM   37  C   UNK     0       9.697  -6.628   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      11.168  -7.082   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       8.568  -7.676   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   35   37                                             
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6    7   35                                             
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   11   17                                             
CONECT   10    9                                                            
CONECT   11    9   12   13   35                                             
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   17   33                                             
CONECT   16   15                                                            
CONECT   17   15    9   18   19                                             
CONECT   18   17                                                            
CONECT   19   17   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22   23   33                                             
CONECT   22   21                                                            
CONECT   23   21   24   25   26                                             
CONECT   24   23                                                            
CONECT   25   23                                                            
CONECT   26   23   27   28   29                                             
CONECT   27   26                                                            
CONECT   28   26                                                            
CONECT   29   26   30                                                       
CONECT   30   29   31   32   33                                             
CONECT   31   30                                                            
CONECT   32   30                                                            
CONECT   33   30   15   21   34                                             
CONECT   34   33                                                            
CONECT   35   11    2    5   36                                             
CONECT   36   35                                                            
CONECT   37    2   38   39                                                  
CONECT   38   37                                                            
CONECT   39   37                                                            
MASTER        0    0    0    0    0    0    0    0   39    0   86    0
END

View in JSmol

Synonyms

Value	Source
3-Epi-glochidiol	ChEBI
20(29)-Lupene-1b,3b-diol	Generator
20(29)-Lupene-1β,3β-diol	Generator

Chemical Formula

C₃₀H₅₀O₂

Average Mass

442.7280 Da

Monoisotopic Mass

442.38108 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

29028-10-2

SMILES

[H][C@]1(CC[C@]2(C)CC[C@]3(C)[C@]([H])(CC[C@@]4([H])[C@@]3(C)CC[C@@]3([H])C(C)(C)[C@@]([H])(O)C[C@@]([H])(O)[C@]43C)[C@@]12[H])C(C)=C

InChI Identifier

InChI=1S/C30H50O2/c1-18(2)19-11-13-27(5)15-16-28(6)20(25(19)27)9-10-22-29(28,7)14-12-21-26(3,4)23(31)17-24(32)30(21,22)8/h19-25,31-32H,1,9-17H2,2-8H3/t19-,20+,21-,22-,23-,24+,25+,27+,28+,29+,30-/m0/s1

InChI Key

SWEUJTWPRYKNNX-AXLUDCLJSA-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
Breynia fruticosa	LOTUS Database	35616633
Celastrus hypoleucus	LOTUS Database	35616633
Glochidion eriocarpum	LOTUS Database	35616633
Glochidion puberum	LOTUS Database	35616633
Glochidion zeylanicum	LOTUS Database	35616633
Salvia deserta	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Triterpenoids

Direct Parent

Triterpenoids

Alternative Parents

Substituents

Triterpenoid
Steroid
Cyclic alcohol
Secondary alcohol
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Alcohol
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

diol (CHEBI:67599 )
pentacyclic triterpenoid (CHEBI:67599 )

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

427858

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

488250

PDB ID

Not Available

ChEBI ID

67599

Good Scents ID

Not Available

References

General References

Liu YP, Cai XH, Feng T, Li Y, Li XN, Luo XD: Triterpene and sterol derivatives from the roots of Breynia fruticosa. J Nat Prod. 2011 May 27;74(5):1161-8. doi: 10.1021/np2000914. Epub 2011 Mar 23. [PubMed:21428418 ]
Wang KW, Mao JS, Tai YP, Pan YJ: Novel skeleton terpenes from Celastrus hypoleucus with anti-tumor activities. Bioorg Med Chem Lett. 2006 Apr 15;16(8):2274-7. doi: 10.1016/j.bmcl.2006.01.021. Epub 2006 Feb 7. [PubMed:16455245 ]

Showing NP-Card for 3-Epiglochidiol (NP0137676)

MOL for NP0137676 (3-Epiglochidiol)

3D MOL for NP0137676 (3-Epiglochidiol)

3D SDF for NP0137676 (3-Epiglochidiol)

3D-SDF for NP0137676 (3-Epiglochidiol)

PDB for NP0137676 (3-Epiglochidiol)

3D PDB for NP0137676 (3-Epiglochidiol)

SMILES for NP0137676 (3-Epiglochidiol)

INCHI for NP0137676 (3-Epiglochidiol)

Structure for NP0137676 (3-Epiglochidiol)

3D Structure for NP0137676 (3-Epiglochidiol)