NP-MRD: Showing NP-Card for 3,4a,8,12a-tetrahydroxy-12b-[(5-hydroxy-6-methyloxan-2-yl)oxy]-3-methyl-4,5,6,6a-tetrahydro-2h-tetraphene-1,7,12-trione (NP0245850)

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Record Information

Version

2.0

Created at

2022-09-07 07:05:15 UTC

Updated at

2022-09-07 07:05:15 UTC

NP-MRD ID

NP0245850

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3,4a,8,12a-tetrahydroxy-12b-[(5-hydroxy-6-methyloxan-2-yl)oxy]-3-methyl-4,5,6,6a-tetrahydro-2h-tetraphene-1,7,12-trione

Description

3,4A,8,12a-tetrahydroxy-12b-[(5-hydroxy-6-methyloxan-2-yl)oxy]-3-methyl-1,2,3,4,4a,5,6,6a,7,12,12a,12b-dodecahydrotetraphene-1,7,12-trione belongs to the class of organic compounds known as anthraquinone glycosides. These are organic compounds containing an anthraquinone moiety glycosidically bound to a carbohydrate moiety. 3,4a,8,12a-tetrahydroxy-12b-[(5-hydroxy-6-methyloxan-2-yl)oxy]-3-methyl-4,5,6,6a-tetrahydro-2h-tetraphene-1,7,12-trione is found in Streptomyces fradiae. 3,4A,8,12a-tetrahydroxy-12b-[(5-hydroxy-6-methyloxan-2-yl)oxy]-3-methyl-1,2,3,4,4a,5,6,6a,7,12,12a,12b-dodecahydrotetraphene-1,7,12-trione is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004161519232D          

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M  END

     RDKit          3D

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M  END


  Mrv1533004161519232D          

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M  END
> <DATABASE_ID>
NP0245850

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1OC(CCC1O)OC12C(=O)CC(C)(O)CC1(O)CCC1C(=O)C3=C(O)C=CC=C3C(=O)C21O

> <INCHI_IDENTIFIER>
InChI=1S/C25H30O10/c1-12-15(26)6-7-18(34-12)35-25-17(28)10-22(2,31)11-23(25,32)9-8-14-20(29)19-13(4-3-5-16(19)27)21(30)24(14,25)33/h3-5,12,14-15,18,26-27,31-33H,6-11H2,1-2H3

> <INCHI_KEY>
BDZBETDENXLJSX-UHFFFAOYSA-N

> <FORMULA>
C25H30O10

> <MOLECULAR_WEIGHT>
490.505

> <EXACT_MASS>
490.183897166

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
65

> <JCHEM_AVERAGE_POLARIZABILITY>
48.369208289195576

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3,4a,8,12a-tetrahydroxy-12b-[(5-hydroxy-6-methyloxan-2-yl)oxy]-3-methyl-1,2,3,4,4a,5,6,6a,7,12,12a,12b-dodecahydrotetraphene-1,7,12-trione

> <ALOGPS_LOGP>
0.78

> <JCHEM_LOGP>
0.5907687070000005

> <ALOGPS_LOGS>
-2.01

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.787894248522885

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.087754348605651

> <JCHEM_PKA_STRONGEST_BASIC>
-2.899240557939863

> <JCHEM_POLAR_SURFACE_AREA>
170.81999999999996

> <JCHEM_REFRACTIVITY>
119.50239999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.74e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3,4a,8,12a-tetrahydroxy-12b-[(5-hydroxy-6-methyloxan-2-yl)oxy]-3-methyl-4,5,6,6a-tetrahydro-2H-tetraphene-1,7,12-trione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 16-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   16-APR-15         0                                  
HETATM    1  C   UNK     0       5.156  -8.215   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.668  -7.924   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       7.172  -6.469   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       8.685  -6.178   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       9.693  -7.342   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.189  -8.798   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.677  -9.089   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       7.172 -10.544   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0       9.189  -4.723   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       8.181  -3.559   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.677  -5.014   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       7.808  -6.549   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       6.164  -5.305   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.156  -4.141   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.185  -5.336   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       3.811  -3.392   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       5.660  -2.686   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       7.172  -2.395   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       6.164  -1.231   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       7.677  -0.940   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       9.189  -0.649   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      10.197  -1.813   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      11.709  -1.522   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      12.213  -0.067   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      12.717  -2.686   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      14.230  -2.395   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      14.734  -0.940   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      15.238  -3.559   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      14.734  -5.014   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      13.221  -5.305   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      12.213  -4.141   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      10.701  -4.432   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      10.197  -5.887   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       9.693  -3.268   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0      10.140  -4.741   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    7                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    9                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    2    8                                                  
CONECT    8    7                                                            
CONECT    9    4   10                                                       
CONECT   10    9   11   18   34                                             
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13   15   16   17                                             
CONECT   15   14                                                            
CONECT   16   14                                                            
CONECT   17   14   18                                                       
CONECT   18   17   10   19   20                                             
CONECT   19   18                                                            
CONECT   20   18   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23   34                                                  
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26   31                                                  
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   25   32                                                  
CONECT   32   31   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32   10   22   35                                             
CONECT   35   34                                                            
MASTER        0    0    0    0    0    0    0    0   35    0   78    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₅H₃₀O₁₀

Average Mass

490.5050 Da

Monoisotopic Mass

490.18390 Da

IUPAC Name

3,4a,8,12a-tetrahydroxy-12b-[(5-hydroxy-6-methyloxan-2-yl)oxy]-3-methyl-1,2,3,4,4a,5,6,6a,7,12,12a,12b-dodecahydrotetraphene-1,7,12-trione

Traditional Name

3,4a,8,12a-tetrahydroxy-12b-[(5-hydroxy-6-methyloxan-2-yl)oxy]-3-methyl-4,5,6,6a-tetrahydro-2H-tetraphene-1,7,12-trione

CAS Registry Number

Not Available

SMILES

CC1OC(CCC1O)OC12C(=O)CC(C)(O)CC1(O)CCC1C(=O)C3=C(O)C=CC=C3C(=O)C21O

InChI Identifier

InChI=1S/C25H30O10/c1-12-15(26)6-7-18(34-12)35-25-17(28)10-22(2,31)11-23(25,32)9-8-14-20(29)19-13(4-3-5-16(19)27)21(30)24(14,25)33/h3-5,12,14-15,18,26-27,31-33H,6-11H2,1-2H3

InChI Key

BDZBETDENXLJSX-UHFFFAOYSA-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
Streptomyces fradiae	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as anthraquinone glycosides. These are organic compounds containing an anthraquinone moiety glycosidically bound to a carbohydrate moiety.

Kingdom

Super Class

Class

Sub Class

Direct Parent

Anthraquinone glycosides

Alternative Parents

Substituents

Anthraquinone glycoside
Hydroxyanthraquinone
Naphthalene
Tetralin
Aryl alkyl ketone
Aryl ketone
Quinone
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Oxane
Cyclic alcohol
Vinylogous acid
Tertiary alcohol
Ketone
Secondary alcohol
Organoheterocyclic compound
Oxacycle
Acetal
Polyol
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Carbonyl group
Organic oxygen compound
Alcohol
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	0.78	ALOGPS
logP	0.59	ChemAxon
logS	-2	ALOGPS
pKa (Strongest Acidic)	8.09	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	170.82 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	119.5 m³·mol⁻¹	ChemAxon
Polarizability	48.37 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	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

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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 3,4a,8,12a-tetrahydroxy-12b-[(5-hydroxy-6-methyloxan-2-yl)oxy]-3-methyl-4,5,6,6a-tetrahydro-2h-tetraphene-1,7,12-trione (NP0245850)

MOL for NP0245850 (3,4a,8,12a-tetrahydroxy-12b-[(5-hydroxy-6-methyloxan-2-yl)oxy]-3-methyl-4,5,6,6a-tetrahydro-2h-tetraphene-1,7,12-trione)

3D MOL for NP0245850 (3,4a,8,12a-tetrahydroxy-12b-[(5-hydroxy-6-methyloxan-2-yl)oxy]-3-methyl-4,5,6,6a-tetrahydro-2h-tetraphene-1,7,12-trione)

3D SDF for NP0245850 (3,4a,8,12a-tetrahydroxy-12b-[(5-hydroxy-6-methyloxan-2-yl)oxy]-3-methyl-4,5,6,6a-tetrahydro-2h-tetraphene-1,7,12-trione)

3D-SDF for NP0245850 (3,4a,8,12a-tetrahydroxy-12b-[(5-hydroxy-6-methyloxan-2-yl)oxy]-3-methyl-4,5,6,6a-tetrahydro-2h-tetraphene-1,7,12-trione)

PDB for NP0245850 (3,4a,8,12a-tetrahydroxy-12b-[(5-hydroxy-6-methyloxan-2-yl)oxy]-3-methyl-4,5,6,6a-tetrahydro-2h-tetraphene-1,7,12-trione)

3D PDB for NP0245850 (3,4a,8,12a-tetrahydroxy-12b-[(5-hydroxy-6-methyloxan-2-yl)oxy]-3-methyl-4,5,6,6a-tetrahydro-2h-tetraphene-1,7,12-trione)

SMILES for NP0245850 (3,4a,8,12a-tetrahydroxy-12b-[(5-hydroxy-6-methyloxan-2-yl)oxy]-3-methyl-4,5,6,6a-tetrahydro-2h-tetraphene-1,7,12-trione)

INCHI for NP0245850 (3,4a,8,12a-tetrahydroxy-12b-[(5-hydroxy-6-methyloxan-2-yl)oxy]-3-methyl-4,5,6,6a-tetrahydro-2h-tetraphene-1,7,12-trione)

Structure for NP0245850 (3,4a,8,12a-tetrahydroxy-12b-[(5-hydroxy-6-methyloxan-2-yl)oxy]-3-methyl-4,5,6,6a-tetrahydro-2h-tetraphene-1,7,12-trione)

3D Structure for NP0245850 (3,4a,8,12a-tetrahydroxy-12b-[(5-hydroxy-6-methyloxan-2-yl)oxy]-3-methyl-4,5,6,6a-tetrahydro-2h-tetraphene-1,7,12-trione)