NP-MRD: Showing NP-Card for teucrolin F (NP0028977)

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Record Information

Version

2.0

Created at

2021-06-19 20:43:13 UTC

Updated at

2021-06-29 23:56:04 UTC

NP-MRD ID

NP0028977

Secondary Accession Numbers

None

Natural Product Identification

Common Name

teucrolin F

Provided By

JEOL Database JEOL Logo

Description

teucrolin F is found in Teucrium oliverianum. teucrolin F was first documented in 2002 (Al-Yahya, M. A., et al.). Based on a literature review very few articles have been published on [(1R,2S,4aR,5R,6S,7R,8R,8aR)-8-(acetyloxy)-5-[2-(furan-3-yl)ethyl]-2,7-dihydroxy-5,6-dimethyl-octahydro-2H-spiro[naphthalene-1,2'-oxirane]-8a-yl]methyl acetate.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306192122433D          

 66 69  0  0  0  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652306192122433D          

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M  END
> <DATABASE_ID>
NP0028977

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]O[C@@]1([H])[C@]([H])(OC(=O)C([H])([H])[H])[C@]2(C([H])([H])OC(=O)C([H])([H])[H])[C@]([H])(C([H])([H])C([H])([H])[C@]([H])(O[H])[C@@]22OC2([H])[H])[C@@](C([H])([H])[H])(C([H])([H])C([H])([H])C2=C([H])OC([H])=C2[H])[C@]1([H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C24H34O8/c1-14-20(28)21(32-16(3)26)23(12-30-15(2)25)18(5-6-19(27)24(23)13-31-24)22(14,4)9-7-17-8-10-29-11-17/h8,10-11,14,18-21,27-28H,5-7,9,12-13H2,1-4H3/t14-,18-,19+,20-,21+,22+,23+,24-/m1/s1

> <INCHI_KEY>
RGEIXNHVBDLHCF-HYDHIAQQSA-N

> <FORMULA>
C24H34O8

> <MOLECULAR_WEIGHT>
450.528

> <EXACT_MASS>
450.225368055

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
66

> <JCHEM_AVERAGE_POLARIZABILITY>
47.390838597804745

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
[(1R,2S,4aR,5R,6S,7R,8R,8aR)-8-(acetyloxy)-5-[2-(furan-3-yl)ethyl]-2,7-dihydroxy-5,6-dimethyl-octahydro-2H-spiro[naphthalene-1,2'-oxirane]-8a-yl]methyl acetate

> <ALOGPS_LOGP>
2.29

> <JCHEM_LOGP>
1.4675551856666669

> <ALOGPS_LOGS>
-3.62

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.196437624014088

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.59418081690135

> <JCHEM_PKA_STRONGEST_BASIC>
-2.7687105772542773

> <JCHEM_POLAR_SURFACE_AREA>
118.73000000000002

> <JCHEM_REFRACTIVITY>
112.38730000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.08e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2S,4aR,5R,6S,7R,8R,8aR)-8-(acetyloxy)-5-[2-(furan-3-yl)ethyl]-2,7-dihydroxy-5,6-dimethyl-hexahydro-2H-spiro[naphthalene-1,2'-oxirane]-8a-ylmethyl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 66 69  0  0  0  0  0  0  0  0999 V2000
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 31 64  1  0
 31 65  1  0
 31 66  1  0
M  END

HEADER    PROTEIN                                 19-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-JUN-21         0                                  
HETATM    1  C   UNK     0      -1.958  -1.891  -4.897  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.705  -2.649  -3.630  0.00  0.00           C+0
HETATM    3  O   UNK     0      -1.563  -3.860  -3.562  0.00  0.00           O+0
HETATM    4  O   UNK     0      -1.654  -1.787  -2.576  0.00  0.00           O+0
HETATM    5  C   UNK     0      -1.419  -2.406  -1.308  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.312  -1.369  -0.136  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.560  -0.002  -0.436  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.317   0.912  -1.440  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.775   1.145  -1.046  0.00  0.00           C+0
HETATM   10  C   UNK     0      -3.518  -0.154  -0.788  0.00  0.00           C+0
HETATM   11  O   UNK     0      -4.841   0.164  -0.356  0.00  0.00           O+0
HETATM   12  C   UNK     0      -2.776  -0.961   0.259  0.00  0.00           C+0
HETATM   13  C   UNK     0      -3.264  -0.906   1.707  0.00  0.00           C+0
HETATM   14  O   UNK     0      -3.569  -2.009   0.844  0.00  0.00           O+0
HETATM   15  C   UNK     0       1.000  -0.105  -0.701  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.316  -0.802  -2.047  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.645   1.329  -0.837  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.506   2.272   0.368  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.108   3.611   0.094  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.461   4.753  -0.458  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.410   5.745  -0.524  0.00  0.00           C+0
HETATM   22  O   UNK     0       3.599   5.295  -0.049  0.00  0.00           O+0
HETATM   23  C   UNK     0       3.411   4.005   0.324  0.00  0.00           C+0
HETATM   24  C   UNK     0       1.658  -0.886   0.497  0.00  0.00           C+0
HETATM   25  C   UNK     0       3.176  -1.108   0.341  0.00  0.00           C+0
HETATM   26  C   UNK     0       0.963  -2.230   0.799  0.00  0.00           C+0
HETATM   27  O   UNK     0       1.598  -2.816   1.948  0.00  0.00           O+0
HETATM   28  C   UNK     0      -0.557  -2.064   1.046  0.00  0.00           C+0
HETATM   29  O   UNK     0      -1.129  -3.377   1.271  0.00  0.00           O+0
HETATM   30  C   UNK     0      -1.147  -3.821   2.556  0.00  0.00           C+0
HETATM   31  C   UNK     0      -1.802  -5.164   2.634  0.00  0.00           C+0
HETATM   32  O   UNK     0      -0.685  -3.210   3.510  0.00  0.00           O+0
HETATM   33  H   UNK     0      -1.136  -1.194  -5.080  0.00  0.00           H+0
HETATM   34  H   UNK     0      -2.015  -2.592  -5.734  0.00  0.00           H+0
HETATM   35  H   UNK     0      -2.908  -1.355  -4.825  0.00  0.00           H+0
HETATM   36  H   UNK     0      -0.512  -3.011  -1.385  0.00  0.00           H+0
HETATM   37  H   UNK     0      -2.245  -3.103  -1.113  0.00  0.00           H+0
HETATM   38  H   UNK     0      -0.640   0.543   0.518  0.00  0.00           H+0
HETATM   39  H   UNK     0      -0.852   1.901  -1.483  0.00  0.00           H+0
HETATM   40  H   UNK     0      -1.271   0.520  -2.458  0.00  0.00           H+0
HETATM   41  H   UNK     0      -3.287   1.722  -1.826  0.00  0.00           H+0
HETATM   42  H   UNK     0      -2.810   1.774  -0.146  0.00  0.00           H+0
HETATM   43  H   UNK     0      -3.630  -0.722  -1.715  0.00  0.00           H+0
HETATM   44  H   UNK     0      -5.257  -0.689  -0.132  0.00  0.00           H+0
HETATM   45  H   UNK     0      -2.612  -1.095   2.547  0.00  0.00           H+0
HETATM   46  H   UNK     0      -4.070  -0.226   1.967  0.00  0.00           H+0
HETATM   47  H   UNK     0       2.375  -0.695  -2.311  0.00  0.00           H+0
HETATM   48  H   UNK     0       1.120  -1.873  -2.032  0.00  0.00           H+0
HETATM   49  H   UNK     0       0.750  -0.363  -2.874  0.00  0.00           H+0
HETATM   50  H   UNK     0       2.714   1.229  -1.067  0.00  0.00           H+0
HETATM   51  H   UNK     0       1.240   1.825  -1.728  0.00  0.00           H+0
HETATM   52  H   UNK     0       0.452   2.417   0.628  0.00  0.00           H+0
HETATM   53  H   UNK     0       1.996   1.844   1.248  0.00  0.00           H+0
HETATM   54  H   UNK     0       0.430   4.841  -0.770  0.00  0.00           H+0
HETATM   55  H   UNK     0       2.401   6.771  -0.863  0.00  0.00           H+0
HETATM   56  H   UNK     0       4.282   3.506   0.728  0.00  0.00           H+0
HETATM   57  H   UNK     0       1.543  -0.279   1.405  0.00  0.00           H+0
HETATM   58  H   UNK     0       3.714  -0.170   0.184  0.00  0.00           H+0
HETATM   59  H   UNK     0       3.603  -1.552   1.247  0.00  0.00           H+0
HETATM   60  H   UNK     0       3.402  -1.782  -0.491  0.00  0.00           H+0
HETATM   61  H   UNK     0       1.142  -2.945  -0.009  0.00  0.00           H+0
HETATM   62  H   UNK     0       1.057  -2.643   2.745  0.00  0.00           H+0
HETATM   63  H   UNK     0      -0.669  -1.452   1.948  0.00  0.00           H+0
HETATM   64  H   UNK     0      -2.828  -5.097   2.264  0.00  0.00           H+0
HETATM   65  H   UNK     0      -1.829  -5.494   3.676  0.00  0.00           H+0
HETATM   66  H   UNK     0      -1.229  -5.890   2.051  0.00  0.00           H+0
CONECT    1    2   33   34   35                                             
CONECT    2    4    1    3                                                  
CONECT    3    2                                                            
CONECT    4    5    2                                                       
CONECT    5    6    4   36   37                                             
CONECT    6   28   12    7    5                                             
CONECT    7    8    6   15   38                                             
CONECT    8    7    9   39   40                                             
CONECT    9   10    8   41   42                                             
CONECT   10   12    9   11   43                                             
CONECT   11   10   44                                                       
CONECT   12   10    6   13   14                                             
CONECT   13   12   14   45   46                                             
CONECT   14   12   13                                                       
CONECT   15   24   17   16    7                                             
CONECT   16   15   47   48   49                                             
CONECT   17   15   18   50   51                                             
CONECT   18   19   17   52   53                                             
CONECT   19   18   23   20                                                  
CONECT   20   21   19   54                                                  
CONECT   21   22   20   55                                                  
CONECT   22   23   21                                                       
CONECT   23   19   22   56                                                  
CONECT   24   26   15   25   57                                             
CONECT   25   24   58   59   60                                             
CONECT   26   28   24   27   61                                             
CONECT   27   26   62                                                       
CONECT   28    6   26   29   63                                             
CONECT   29   28   30                                                       
CONECT   30   29   31   32                                                  
CONECT   31   30   64   65   66                                             
CONECT   32   30                                                            
CONECT   33    1                                                            
CONECT   34    1                                                            
CONECT   35    1                                                            
CONECT   36    5                                                            
CONECT   37    5                                                            
CONECT   38    7                                                            
CONECT   39    8                                                            
CONECT   40    8                                                            
CONECT   41    9                                                            
CONECT   42    9                                                            
CONECT   43   10                                                            
CONECT   44   11                                                            
CONECT   45   13                                                            
CONECT   46   13                                                            
CONECT   47   16                                                            
CONECT   48   16                                                            
CONECT   49   16                                                            
CONECT   50   17                                                            
CONECT   51   17                                                            
CONECT   52   18                                                            
CONECT   53   18                                                            
CONECT   54   20                                                            
CONECT   55   21                                                            
CONECT   56   23                                                            
CONECT   57   24                                                            
CONECT   58   25                                                            
CONECT   59   25                                                            
CONECT   60   25                                                            
CONECT   61   26                                                            
CONECT   62   27                                                            
CONECT   63   28                                                            
CONECT   64   31                                                            
CONECT   65   31                                                            
CONECT   66   31                                                            
MASTER        0    0    0    0    0    0    0    0   66    0  138    0
END

RDKit          3D

66 69  0  0  0  0  0  0  0  0999 V2000
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 31 65  1  0
 31 66  1  0
M  END

View in JSmol

Synonyms

Value	Source
[(1R,2S,4AR,5R,6S,7R,8R,8ar)-8-(acetyloxy)-5-[2-(furan-3-yl)ethyl]-2,7-dihydroxy-5,6-dimethyl-octahydro-2H-spiro[naphthalene-1,2'-oxirane]-8a-yl]methyl acetic acid	Generator

Chemical Formula

C₂₄H₃₄O₈

Average Mass

450.5280 Da

Monoisotopic Mass

450.22537 Da

IUPAC Name

[(1R,2S,4aR,5R,6S,7R,8R,8aR)-8-(acetyloxy)-5-[2-(furan-3-yl)ethyl]-2,7-dihydroxy-5,6-dimethyl-octahydro-2H-spiro[naphthalene-1,2'-oxirane]-8a-yl]methyl acetate

Traditional Name

(1R,2S,4aR,5R,6S,7R,8R,8aR)-8-(acetyloxy)-5-[2-(furan-3-yl)ethyl]-2,7-dihydroxy-5,6-dimethyl-hexahydro-2H-spiro[naphthalene-1,2'-oxirane]-8a-ylmethyl acetate

CAS Registry Number

Not Available

SMILES

[H]O[C@@]1([H])[C@]([H])(OC(=O)C([H])([H])[H])[C@]2(C([H])([H])OC(=O)C([H])([H])[H])[C@]([H])(C([H])([H])C([H])([H])[C@]([H])(O[H])[C@@]22OC2([H])[H])[C@@](C([H])([H])[H])(C([H])([H])C([H])([H])C2=C([H])OC([H])=C2[H])[C@]1([H])C([H])([H])[H]

InChI Identifier

InChI=1S/C24H34O8/c1-14-20(28)21(32-16(3)26)23(12-30-15(2)25)18(5-6-19(27)24(23)13-31-24)22(14,4)9-7-17-8-10-29-11-17/h8,10-11,14,18-21,27-28H,5-7,9,12-13H2,1-4H3/t14-,18-,19+,20-,21+,22+,23+,24-/m1/s1

InChI Key

RGEIXNHVBDLHCF-HYDHIAQQSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Teucrium oliverianum	JEOL database	Al-Yahya, M. A., et al, Phytochemistry 59, 409 (2002)

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as dicarboxylic acids and derivatives. These are organic compounds containing exactly two carboxylic acid groups.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Dicarboxylic acids and derivatives

Direct Parent

Dicarboxylic acids and derivatives

Alternative Parents

Substituents

Dicarboxylic acid or derivatives
Cyclic alcohol
Furan
Heteroaromatic compound
Secondary alcohol
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Ether
Oxirane
Dialkyl ether
Organooxygen compound
Organic oxygen compound
Alcohol
Carbonyl group
Hydrocarbon derivative
Organic oxide
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic 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	2.29	ALOGPS
logP	1.47	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Acidic)	13.59	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	118.73 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	112.39 m³·mol⁻¹	ChemAxon
Polarizability	47.39 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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

552299

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

636533

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Al-Yahya, M. A., et al. (2002). Al-Yahya, M. A., et al, Phytochemistry 59, 409 (2002). Phytochem..

Showing NP-Card for teucrolin F (NP0028977)

MOL for NP0028977 (teucrolin F)

3D MOL for NP0028977 (teucrolin F)

3D SDF for NP0028977 (teucrolin F)

3D-SDF for NP0028977 (teucrolin F)

PDB for NP0028977 (teucrolin F)

3D PDB for NP0028977 (teucrolin F)

SMILES for NP0028977 (teucrolin F)

INCHI for NP0028977 (teucrolin F)

Structure for NP0028977 (teucrolin F)

3D Structure for NP0028977 (teucrolin F)