NP-MRD: Showing NP-Card for (-)-25R-Spirost-4-ene-3,12-dione (NP0077457)

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Record Information

Version

2.0

Created at

2022-04-28 22:36:28 UTC

Updated at

2022-04-28 22:36:28 UTC

NP-MRD ID

NP0077457

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(-)-25R-Spirost-4-ene-3,12-dione

Description

(25R)-Spirost-4-ene-3,12-dione belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units. (-)-25R-Spirost-4-ene-3,12-dione is found in Polygonum chinensis L. and Tribulus terrestris. Based on a literature review very few articles have been published on (25R)-Spirost-4-ene-3,12-dione.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304292200362D          

 31 36  0  0  1  0            999 V2000
    7.0487    4.8600    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4190    4.1227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    6.9656    3.4334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1420    3.4814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7717    4.2186    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.2251    4.9079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9481    4.2665    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
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    4.8651    2.8400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6887    2.7921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6712    3.6252    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.3009    4.3624    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.7543    5.0517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3840    5.7890    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5779    5.0038    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

     RDKit          3D

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M  END


  Mrv1652304292200362D          

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M  END
> <DATABASE_ID>
NP0077457

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@H]1[C@H]2[C@H](C[C@H]3[C@@H]4CCC5=CC(=O)CC[C@]5(C)[C@H]4CC(=O)[C@]23C)O[C@]11CC[C@@H](C)CO1

> <INCHI_IDENTIFIER>
InChI=1S/C27H38O4/c1-15-7-10-27(30-14-15)16(2)24-22(31-27)12-21-19-6-5-17-11-18(28)8-9-25(17,3)20(19)13-23(29)26(21,24)4/h11,15-16,19-22,24H,5-10,12-14H2,1-4H3/t15-,16+,19-,20+,21+,22+,24+,25+,26-,27-/m1/s1

> <INCHI_KEY>
ZVWYBBDTSJOAHD-HGMFYQPQSA-N

> <FORMULA>
C27H38O4

> <MOLECULAR_WEIGHT>
426.597

> <EXACT_MASS>
426.277009704

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
69

> <JCHEM_AVERAGE_POLARIZABILITY>
50.12282783518994

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1'R,2R,2'S,4'S,5R,7'S,8'R,9'S,12'S,13'R)-5,7',9',13'-tetramethyl-5'-oxaspiro[oxane-2,6'-pentacyclo[10.8.0.0^{2,9}.0^{4,8}.0^{13,18}]icosan]-17'-ene-10',16'-dione

> <ALOGPS_LOGP>
3.60

> <JCHEM_LOGP>
4.827268040666667

> <ALOGPS_LOGS>
-5.45

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
19.006607815924855

> <JCHEM_PKA_STRONGEST_BASIC>
-3.9812775376182103

> <JCHEM_POLAR_SURFACE_AREA>
52.60000000000001

> <JCHEM_REFRACTIVITY>
119.90769999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.52e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1'R,2R,2'S,4'S,5R,7'S,8'R,9'S,12'S,13'R)-5,7',9',13'-tetramethyl-5'-oxaspiro[oxane-2,6'-pentacyclo[10.8.0.0^{2,9}.0^{4,8}.0^{13,18}]icosan]-17'-ene-10',16'-dione

> <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      13.158   9.072   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      13.849   7.696   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      15.386   7.606   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      13.003   6.409   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      11.465   6.499   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      10.774   7.875   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      11.620   9.161   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.237   7.964   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.390   6.678   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.082   5.301   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      10.619   5.212   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.853   6.767   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.162   8.143   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.008   9.430   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       6.317  10.806   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       8.545   9.340   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.639   7.911   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.390   6.391   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.758   5.684   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       2.867   6.159   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       2.176   7.536   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       3.271   8.618   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       3.039  10.141   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       1.200   6.344   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      -0.320   6.594   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -0.863   8.035   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       0.113   9.226   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       1.632   8.976   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -2.383   8.285   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       5.330   9.440   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      10.083   9.251   0.000  0.00  0.00           C+0
CONECT    1    2    7                                                       
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6   11                                                  
CONECT    6    5    7    8   31                                             
CONECT    7    6    1                                                       
CONECT    8    6    9   16                                                  
CONECT    9    8   10   12                                                  
CONECT   10    9   11                                                       
CONECT   11   10    5                                                       
CONECT   12    9   13   19                                                  
CONECT   13   12   14   17   30                                             
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14    8                                                       
CONECT   17   13   18   22                                                  
CONECT   18   17   19   20                                                  
CONECT   19   18   12                                                       
CONECT   20   18   21                                                       
CONECT   21   20   22   24   28                                             
CONECT   22   21   17   23                                                  
CONECT   23   22                                                            
CONECT   24   21   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27   29                                                  
CONECT   27   26   28                                                       
CONECT   28   27   21                                                       
CONECT   29   26                                                            
CONECT   30   13                                                            
CONECT   31    6                                                            
MASTER        0    0    0    0    0    0    0    0   31    0   72    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₇H₃₈O₄

Average Mass

426.5970 Da

Monoisotopic Mass

426.27701 Da

IUPAC Name

(1'R,2R,2'S,4'S,5R,7'S,8'R,9'S,12'S,13'R)-5,7',9',13'-tetramethyl-5'-oxaspiro[oxane-2,6'-pentacyclo[10.8.0.0^{2,9}.0^{4,8}.0^{13,18}]icosan]-17'-ene-10',16'-dione

Traditional Name

(1'R,2R,2'S,4'S,5R,7'S,8'R,9'S,12'S,13'R)-5,7',9',13'-tetramethyl-5'-oxaspiro[oxane-2,6'-pentacyclo[10.8.0.0^{2,9}.0^{4,8}.0^{13,18}]icosan]-17'-ene-10',16'-dione

CAS Registry Number

Not Available

SMILES

C[C@H]1[C@H]2[C@H](C[C@H]3[C@@H]4CCC5=CC(=O)CC[C@]5(C)[C@H]4CC(=O)[C@]23C)O[C@]11CC[C@@H](C)CO1

InChI Identifier

InChI=1S/C27H38O4/c1-15-7-10-27(30-14-15)16(2)24-22(31-27)12-21-19-6-5-17-11-18(28)8-9-25(17,3)20(19)13-23(29)26(21,24)4/h11,15-16,19-22,24H,5-10,12-14H2,1-4H3/t15-,16+,19-,20+,21+,22+,24+,25+,26-,27-/m1/s1

InChI Key

ZVWYBBDTSJOAHD-HGMFYQPQSA-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
Polygonum chinensis L.	Plant	KNApSAcK
Tribulus terrestris	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
Spirostane skeleton
3-oxo-delta-4-steroid
3-oxosteroid
12-oxosteroid
Oxosteroid
Delta-4-steroid
Steroid
Ketal
Cyclohexenone
Oxane
Tetrahydrofuran
Ketone
Cyclic ketone
Oxacycle
Acetal
Organoheterocyclic compound
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Organic oxygen compound
Carbonyl group
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	3.6	ALOGPS
logP	4.83	ChemAxon
logS	-5.4	ALOGPS
pKa (Strongest Acidic)	19.01	ChemAxon
pKa (Strongest Basic)	-4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	52.6 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	119.91 m³·mol⁻¹	ChemAxon
Polarizability	50.12 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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

9011499

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10836200

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for (-)-25R-Spirost-4-ene-3,12-dione (NP0077457)

MOL for NP0077457 ((-)-25R-Spirost-4-ene-3,12-dione)

3D MOL for NP0077457 ((-)-25R-Spirost-4-ene-3,12-dione)

3D SDF for NP0077457 ((-)-25R-Spirost-4-ene-3,12-dione)

3D-SDF for NP0077457 ((-)-25R-Spirost-4-ene-3,12-dione)

PDB for NP0077457 ((-)-25R-Spirost-4-ene-3,12-dione)

3D PDB for NP0077457 ((-)-25R-Spirost-4-ene-3,12-dione)

SMILES for NP0077457 ((-)-25R-Spirost-4-ene-3,12-dione)

INCHI for NP0077457 ((-)-25R-Spirost-4-ene-3,12-dione)

Structure for NP0077457 ((-)-25R-Spirost-4-ene-3,12-dione)

3D Structure for NP0077457 ((-)-25R-Spirost-4-ene-3,12-dione)