NP-MRD: Showing NP-Card for (2'r,3s,4'ar,4'br,7's,8'ar,10'ar)-2'-[(1e,3e)-2,6-dimethylhepta-1,3,5-trien-1-yl]-7'-hydroxy-4'b,8',8',10'a-tetramethyl-decahydrospiro[oxolane-3,1'-phenanthren]-5-one (NP0284453)

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Record Information

Version

2.0

Created at

2022-09-09 12:09:32 UTC

Updated at

2022-09-09 12:09:32 UTC

NP-MRD ID

NP0284453

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2'r,3s,4'ar,4'br,7's,8'ar,10'ar)-2'-[(1e,3e)-2,6-dimethylhepta-1,3,5-trien-1-yl]-7'-hydroxy-4'b,8',8',10'a-tetramethyl-decahydrospiro[oxolane-3,1'-phenanthren]-5-one

Description

Ebelin lactone belongs to the class of organic compounds known as terpene lactones. These are prenol lipids containing a lactone ring. (2'r,3s,4'ar,4'br,7's,8'ar,10'ar)-2'-[(1e,3e)-2,6-dimethylhepta-1,3,5-trien-1-yl]-7'-hydroxy-4'b,8',8',10'a-tetramethyl-decahydrospiro[oxolane-3,1'-phenanthren]-5-one is found in Colubrina asiatica. (2'r,3s,4'ar,4'br,7's,8'ar,10'ar)-2'-[(1e,3e)-2,6-dimethylhepta-1,3,5-trien-1-yl]-7'-hydroxy-4'b,8',8',10'a-tetramethyl-decahydrospiro[oxolane-3,1'-phenanthren]-5-one was first documented in 2015 (PMID: 25965066). Based on a literature review a small amount of articles have been published on Ebelin lactone (PMID: 35043757) (PMID: 32794231).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309092214092D          

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M  END

     RDKit          3D

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M  END


  Mrv1652309092214092D          

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  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  2  0  0  0  0
 10  9  1  1  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 13 12  1  6  0  0  0
 13 14  1  0  0  0  0
 14 15  1  6  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  6  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
 20 23  1  0  0  0  0
 14 23  1  0  0  0  0
 23 24  1  6  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 13 26  1  0  0  0  0
 26 27  1  6  0  0  0
 26 28  1  0  0  0  0
 10 28  1  0  0  0  0
 28 29  1  1  0  0  0
 29 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
 28 33  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0284453

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)=C\C=C\C(\C)=C\[C@H]1CC[C@@H]2[C@@]3(C)CC[C@H](O)C(C)(C)[C@@H]3CC[C@@]2(C)[C@@]11COC(=O)C1

> <INCHI_IDENTIFIER>
InChI=1S/C30H46O3/c1-20(2)9-8-10-21(3)17-22-11-12-24-28(6)15-14-25(31)27(4,5)23(28)13-16-29(24,7)30(22)18-26(32)33-19-30/h8-10,17,22-25,31H,11-16,18-19H2,1-7H3/b10-8+,21-17+/t22-,23+,24-,25+,28+,29-,30+/m1/s1

> <INCHI_KEY>
TUWRBFMVJOJFCL-SZGKVTBMSA-N

> <FORMULA>
C30H46O3

> <MOLECULAR_WEIGHT>
454.695

> <EXACT_MASS>
454.344695341

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
79

> <JCHEM_AVERAGE_POLARIZABILITY>
55.03872092554292

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2'R,3S,4'aR,4'bR,7'S,8'aR,10'aR)-2'-[(1E,3E)-2,6-dimethylhepta-1,3,5-trien-1-yl]-7'-hydroxy-4'b,8',8',10'a-tetramethyl-dodecahydro-2'H-spiro[oxolane-3,1'-phenanthrene]-5-one

> <JCHEM_LOGP>
6.073142363333334

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
19.489433390169342

> <JCHEM_PKA_STRONGEST_BASIC>
-0.8351215651647189

> <JCHEM_POLAR_SURFACE_AREA>
46.53

> <JCHEM_REFRACTIVITY>
137.73040000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(2'R,3S,4'aR,4'bR,7'S,8'aR,10'aR)-2'-[(1E,3E)-2,6-dimethylhepta-1,3,5-trien-1-yl]-7'-hydroxy-4'b,8',8',10'a-tetramethyl-decahydrospiro[oxolane-3,1'-phenanthrene]-5-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 09-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   09-SEP-22         0                                  
HETATM    1  C   UNK     0      -3.717  -0.980   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.292  -1.562   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.083  -3.087   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.075  -0.618   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.351  -1.200   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.568  -0.256   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.994  -0.839   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.211   0.105   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.203  -2.364   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.628  -2.946   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.845  -2.003   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.271  -2.585   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.480  -4.111   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.906  -4.693   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.697  -3.167   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      10.123  -3.749   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      11.548  -4.331   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      11.757  -5.857   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      13.183  -6.439   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      10.540  -6.801   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      11.681  -7.835   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       9.719  -8.104   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       9.114  -6.219   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       7.897  -7.162   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       6.472  -6.580   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       6.263  -5.054   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       5.397  -6.328   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       4.837  -4.472   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       4.885  -6.012   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       3.436  -6.533   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       2.492  -5.316   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       0.953  -5.364   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       3.358  -4.042   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9   11   28                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   26                                                  
CONECT   14   13   15   16   23                                             
CONECT   15   14                                                            
CONECT   16   14   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21   22   23                                             
CONECT   21   20                                                            
CONECT   22   20                                                            
CONECT   23   20   14   24                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   13   27   28                                             
CONECT   27   26                                                            
CONECT   28   26   10   29   33                                             
CONECT   29   28   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31   28                                                       
MASTER        0    0    0    0    0    0    0    0   33    0   72    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₀H₄₆O₃

Average Mass

454.6950 Da

Monoisotopic Mass

454.34470 Da

IUPAC Name

(2'R,3S,4'aR,4'bR,7'S,8'aR,10'aR)-2'-[(1E,3E)-2,6-dimethylhepta-1,3,5-trien-1-yl]-7'-hydroxy-4'b,8',8',10'a-tetramethyl-dodecahydro-2'H-spiro[oxolane-3,1'-phenanthrene]-5-one

Traditional Name

(2'R,3S,4'aR,4'bR,7'S,8'aR,10'aR)-2'-[(1E,3E)-2,6-dimethylhepta-1,3,5-trien-1-yl]-7'-hydroxy-4'b,8',8',10'a-tetramethyl-decahydrospiro[oxolane-3,1'-phenanthrene]-5-one

CAS Registry Number

Not Available

SMILES

CC(C)=C\C=C\C(\C)=C\[C@H]1CC[C@@H]2[C@@]3(C)CC[C@H](O)C(C)(C)[C@@H]3CC[C@@]2(C)[C@@]11COC(=O)C1

InChI Identifier

InChI=1S/C30H46O3/c1-20(2)9-8-10-21(3)17-22-11-12-24-28(6)15-14-25(31)27(4,5)23(28)13-16-29(24,7)30(22)18-26(32)33-19-30/h8-10,17,22-25,31H,11-16,18-19H2,1-7H3/b10-8+,21-17+/t22-,23+,24-,25+,28+,29-,30+/m1/s1

InChI Key

TUWRBFMVJOJFCL-SZGKVTBMSA-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
Colubrina asiatica	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as terpene lactones. These are prenol lipids containing a lactone ring.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Terpene lactones

Alternative Parents

Substituents

Terpene lactone
Phenanthrene
Monoterpenoid
Gamma butyrolactone
Cyclic alcohol
Tetrahydrofuran
Carboxylic acid ester
Lactone
Secondary alcohol
Carboxylic acid derivative
Oxacycle
Monocarboxylic acid or derivatives
Organoheterocyclic compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Carbonyl group
Alcohol
Organooxygen compound
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	6.07	ChemAxon
pKa (Strongest Acidic)	19.49	ChemAxon
pKa (Strongest Basic)	-0.84	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	46.53 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	137.73 m³·mol⁻¹	ChemAxon
Polarizability	55.04 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	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

66424017

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

15559069

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Ramasamy S, Chin SP, Sukumaran SD, Buckle MJ, Kiew LV, Chung LY: In Silico and In Vitro Analysis of Bacoside A Aglycones and Its Derivatives as the Constituents Responsible for the Cognitive Effects of Bacopa monnieri. PLoS One. 2015 May 12;10(5):e0126565. doi: 10.1371/journal.pone.0126565. eCollection 2015. [PubMed:25965066 ]
Vinod A, Sathianarayanan S, Babu AE, Sadanandan P, Athira K V, Venkidasamy B: Bacopa monnieri for disorders affecting brain: Current perspectives. Curr Top Med Chem. 2022 Jan 19. pii: CTMC-EPUB-120281. doi: 10.2174/1568026622666220119111538. [PubMed:35043757 ]
Shang J, Chen XL, Li L, Zhang H, Yang L, Yang B, Cao L, Wang ZZ, Xiao W: Identification of the absorptive constituents and their metabolites in vivo of Ziziphi Spinosae Semen by UPLC-ESI-Q-TOF-MS/MS. Biomed Chromatogr. 2020 Dec;34(12):e4965. doi: 10.1002/bmc.4965. Epub 2020 Aug 24. [PubMed:32794231 ]
LOTUS database [Link]

Showing NP-Card for (2'r,3s,4'ar,4'br,7's,8'ar,10'ar)-2'-[(1e,3e)-2,6-dimethylhepta-1,3,5-trien-1-yl]-7'-hydroxy-4'b,8',8',10'a-tetramethyl-decahydrospiro[oxolane-3,1'-phenanthren]-5-one (NP0284453)

MOL for NP0284453 ((2'r,3s,4'ar,4'br,7's,8'ar,10'ar)-2'-[(1e,3e)-2,6-dimethylhepta-1,3,5-trien-1-yl]-7'-hydroxy-4'b,8',8',10'a-tetramethyl-decahydrospiro[oxolane-3,1'-phenanthren]-5-one)

3D MOL for NP0284453 ((2'r,3s,4'ar,4'br,7's,8'ar,10'ar)-2'-[(1e,3e)-2,6-dimethylhepta-1,3,5-trien-1-yl]-7'-hydroxy-4'b,8',8',10'a-tetramethyl-decahydrospiro[oxolane-3,1'-phenanthren]-5-one)

3D SDF for NP0284453 ((2'r,3s,4'ar,4'br,7's,8'ar,10'ar)-2'-[(1e,3e)-2,6-dimethylhepta-1,3,5-trien-1-yl]-7'-hydroxy-4'b,8',8',10'a-tetramethyl-decahydrospiro[oxolane-3,1'-phenanthren]-5-one)

3D-SDF for NP0284453 ((2'r,3s,4'ar,4'br,7's,8'ar,10'ar)-2'-[(1e,3e)-2,6-dimethylhepta-1,3,5-trien-1-yl]-7'-hydroxy-4'b,8',8',10'a-tetramethyl-decahydrospiro[oxolane-3,1'-phenanthren]-5-one)

PDB for NP0284453 ((2'r,3s,4'ar,4'br,7's,8'ar,10'ar)-2'-[(1e,3e)-2,6-dimethylhepta-1,3,5-trien-1-yl]-7'-hydroxy-4'b,8',8',10'a-tetramethyl-decahydrospiro[oxolane-3,1'-phenanthren]-5-one)

3D PDB for NP0284453 ((2'r,3s,4'ar,4'br,7's,8'ar,10'ar)-2'-[(1e,3e)-2,6-dimethylhepta-1,3,5-trien-1-yl]-7'-hydroxy-4'b,8',8',10'a-tetramethyl-decahydrospiro[oxolane-3,1'-phenanthren]-5-one)

SMILES for NP0284453 ((2'r,3s,4'ar,4'br,7's,8'ar,10'ar)-2'-[(1e,3e)-2,6-dimethylhepta-1,3,5-trien-1-yl]-7'-hydroxy-4'b,8',8',10'a-tetramethyl-decahydrospiro[oxolane-3,1'-phenanthren]-5-one)

INCHI for NP0284453 ((2'r,3s,4'ar,4'br,7's,8'ar,10'ar)-2'-[(1e,3e)-2,6-dimethylhepta-1,3,5-trien-1-yl]-7'-hydroxy-4'b,8',8',10'a-tetramethyl-decahydrospiro[oxolane-3,1'-phenanthren]-5-one)

Structure for NP0284453 ((2'r,3s,4'ar,4'br,7's,8'ar,10'ar)-2'-[(1e,3e)-2,6-dimethylhepta-1,3,5-trien-1-yl]-7'-hydroxy-4'b,8',8',10'a-tetramethyl-decahydrospiro[oxolane-3,1'-phenanthren]-5-one)

3D Structure for NP0284453 ((2'r,3s,4'ar,4'br,7's,8'ar,10'ar)-2'-[(1e,3e)-2,6-dimethylhepta-1,3,5-trien-1-yl]-7'-hydroxy-4'b,8',8',10'a-tetramethyl-decahydrospiro[oxolane-3,1'-phenanthren]-5-one)