NP-MRD: Showing NP-Card for Teucrolin A (NP0075837)

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Record Information

Version

2.0

Created at

2022-04-28 21:03:45 UTC

Updated at

2022-04-28 21:03:45 UTC

NP-MRD ID

NP0075837

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Teucrolin A

Description

[(2S,4S,6R,6aS,7S,8R,10aR,10bS)-6,8-bis(acetyloxy)-2-(furan-3-yl)-2-hydroxy-4,10b-dimethyl-decahydrospiro[naphtho[4a,4-b]furan-7,2'-oxirane]-6a-yl]methyl acetate belongs to the class of organic compounds known as naphthofurans. Naphthofurans are compounds containing a furan ring fused to a naphthalene moiety. Furan is a 5 membered- ring aromatic ring with four carbon and one oxygen atoms. Naphthalene is a polycyclic aromatic hydrocarbon made up of two fused benzene rings. Teucrolin A is found in Teucrium oliverianum . Based on a literature review very few articles have been published on [(2S,4S,6R,6aS,7S,8R,10aR,10bS)-6,8-bis(acetyloxy)-2-(furan-3-yl)-2-hydroxy-4,10b-dimethyl-decahydrospiro[naphtho[4a,4-b]furan-7,2'-oxirane]-6a-yl]methyl acetate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282223032D          

 36 40  0  0  1  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652304282223032D          

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 22 23  2  0  0  0  0
 19 23  1  0  0  0  0
 17 24  1  1  0  0  0
  7 25  1  6  0  0  0
  4 26  1  1  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 28 30  1  0  0  0  0
  3 31  1  1  0  0  0
 31 32  1  0  0  0  0
  3 32  1  0  0  0  0
  2 33  1  6  0  0  0
 33 34  1  0  0  0  0
 34 35  2  0  0  0  0
 34 36  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0075837

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@H]1C[C@@H](OC(C)=O)[C@]2(COC(C)=O)[C@]3(CO3)[C@@H](CC[C@]22O[C@@](O)(C[C@@]12C)C1=COC=C1)OC(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C26H34O10/c1-15-10-21(35-18(4)29)23(13-32-16(2)27)24(14-33-24)20(34-17(3)28)6-8-26(23)22(15,5)12-25(30,36-26)19-7-9-31-11-19/h7,9,11,15,20-21,30H,6,8,10,12-14H2,1-5H3/t15-,20+,21+,22-,23+,24-,25-,26+/m0/s1

> <INCHI_KEY>
TXKGSLWXTMOCHC-QQINISSKSA-N

> <FORMULA>
C26H34O10

> <MOLECULAR_WEIGHT>
506.548

> <EXACT_MASS>
506.215197295

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
70

> <JCHEM_AVERAGE_POLARIZABILITY>
51.204983822904595

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
[(2S,4S,6R,6aS,7S,8R,10aR,10bS)-6,8-bis(acetyloxy)-2-(furan-3-yl)-2-hydroxy-4,10b-dimethyl-decahydrospiro[naphtho[4a,4-b]furan-7,2'-oxirane]-6a-yl]methyl acetate

> <ALOGPS_LOGP>
2.18

> <JCHEM_LOGP>
1.4147451656666648

> <ALOGPS_LOGS>
-3.62

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.914475758047413

> <JCHEM_PKA_STRONGEST_BASIC>
-2.869157427416532

> <JCHEM_POLAR_SURFACE_AREA>
134.03000000000003

> <JCHEM_REFRACTIVITY>
121.2115

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.22e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S,4S,6R,6aS,7S,8R,10aR,10bS)-6,8-bis(acetyloxy)-2-(furan-3-yl)-2-hydroxy-4,10b-dimethyl-hexahydro-3H-spiro[naphtho[4a,4-b]furan-7,2'-oxirane]-6a-ylmethyl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0       1.642  -0.827   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.106  -0.349   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.424   1.158   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.278   2.187   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.814   1.709   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.903   0.359   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.332   2.737   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.014   4.244   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.450   4.722   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.596   3.694   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       4.060   4.172   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       4.378   5.679   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       5.841   6.157   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       3.231   6.707   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -1.160   5.273   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -1.664   1.965   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -1.342   0.459   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       0.190   0.301   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      -2.801  -0.034   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -3.259  -1.504   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      -4.799  -1.523   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      -5.292  -0.064   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -4.057   0.856   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      -1.675  -1.044   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      -1.579   3.641   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       3.181   3.434   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       4.713   3.276   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       5.616   4.523   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       7.148   4.364   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       6.384   5.858   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       4.453   2.304   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       4.931   0.840   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       4.252  -1.377   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       3.935  -2.884   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0       5.081  -3.913   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0       2.471  -3.362   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    3   33                                                  
CONECT    3    2    4   31   32                                             
CONECT    4    3    5   10   26                                             
CONECT    5    4    6    7   18                                             
CONECT    6    5    1                                                       
CONECT    7    5    8   16   25                                             
CONECT    8    7    9   15                                                  
CONECT    9    8   10                                                       
CONECT   10    9    4   11                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12                                                            
CONECT   15    8                                                            
CONECT   16    7   17                                                       
CONECT   17   16   18   19   24                                             
CONECT   18   17    5                                                       
CONECT   19   17   20   23                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   19                                                       
CONECT   24   17                                                            
CONECT   25    7                                                            
CONECT   26    4   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28                                                            
CONECT   31    3   32                                                       
CONECT   32   31    3                                                       
CONECT   33    2   34                                                       
CONECT   34   33   35   36                                                  
CONECT   35   34                                                            
CONECT   36   34                                                            
MASTER        0    0    0    0    0    0    0    0   36    0   80    0
END

View in JSmol

Synonyms

Value	Source
[(2S,4S,6R,6AS,7S,8R,10ar,10BS)-6,8-bis(acetyloxy)-2-(furan-3-yl)-2-hydroxy-4,10b-dimethyl-decahydrospiro[naphtho[4a,4-b]furan-7,2'-oxirane]-6a-yl]methyl acetic acid	Generator

Chemical Formula

C₂₆H₃₄O₁₀

Average Mass

506.5480 Da

Monoisotopic Mass

506.21520 Da

IUPAC Name

[(2S,4S,6R,6aS,7S,8R,10aR,10bS)-6,8-bis(acetyloxy)-2-(furan-3-yl)-2-hydroxy-4,10b-dimethyl-decahydrospiro[naphtho[4a,4-b]furan-7,2'-oxirane]-6a-yl]methyl acetate

Traditional Name

(2S,4S,6R,6aS,7S,8R,10aR,10bS)-6,8-bis(acetyloxy)-2-(furan-3-yl)-2-hydroxy-4,10b-dimethyl-hexahydro-3H-spiro[naphtho[4a,4-b]furan-7,2'-oxirane]-6a-ylmethyl acetate

CAS Registry Number

Not Available

SMILES

C[C@H]1C[C@@H](OC(C)=O)[C@]2(COC(C)=O)[C@]3(CO3)[C@@H](CC[C@]22O[C@@](O)(C[C@@]12C)C1=COC=C1)OC(C)=O

InChI Identifier

InChI=1S/C26H34O10/c1-15-10-21(35-18(4)29)23(13-32-16(2)27)24(14-33-24)20(34-17(3)28)6-8-26(23)22(15,5)12-25(30,36-26)19-7-9-31-11-19/h7,9,11,15,20-21,30H,6,8,10,12-14H2,1-5H3/t15-,20+,21+,22-,23+,24-,25-,26+/m0/s1

InChI Key

TXKGSLWXTMOCHC-QQINISSKSA-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
Teucrium oliverianum	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as naphthofurans. Naphthofurans are compounds containing a furan ring fused to a naphthalene moiety. Furan is a 5 membered- ring aromatic ring with four carbon and one oxygen atoms. Naphthalene is a polycyclic aromatic hydrocarbon made up of two fused benzene rings.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Naphthofurans

Sub Class

Not Available

Direct Parent

Naphthofurans

Alternative Parents

Substituents

Naphthofuran
Tricarboxylic acid or derivatives
Heteroaromatic compound
Tetrahydrofuran
Furan
Hemiacetal
Carboxylic acid ester
Oxacycle
Ether
Oxirane
Dialkyl ether
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
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	2.18	ALOGPS
logP	1.41	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Acidic)	10.91	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	134.03 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	121.21 m³·mol⁻¹	ChemAxon
Polarizability	51.2 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	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

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

162851075

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Teucrolin A (NP0075837)

MOL for NP0075837 (Teucrolin A)

3D MOL for NP0075837 (Teucrolin A)

3D SDF for NP0075837 (Teucrolin A)

3D-SDF for NP0075837 (Teucrolin A)

PDB for NP0075837 (Teucrolin A)

3D PDB for NP0075837 (Teucrolin A)

SMILES for NP0075837 (Teucrolin A)

INCHI for NP0075837 (Teucrolin A)

Structure for NP0075837 (Teucrolin A)

3D Structure for NP0075837 (Teucrolin A)