NP-MRD: Showing NP-Card for (1s,4ar)-3-acetyl-4a-{[(2s,4r,5s,6r)-4,5-dihydroxy-6-methyloxan-2-yl]oxy}-4,6,7,9-tetrahydroxy-1-methoxy-12,12a-dihydro-1h-tetracene-2,5-dione (NP0291216)

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Record Information

Version

2.0

Created at

2022-09-09 22:13:29 UTC

Updated at

2022-09-09 22:13:29 UTC

NP-MRD ID

NP0291216

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,4ar)-3-acetyl-4a-{[(2s,4r,5s,6r)-4,5-dihydroxy-6-methyloxan-2-yl]oxy}-4,6,7,9-tetrahydroxy-1-methoxy-12,12a-dihydro-1h-tetracene-2,5-dione

Description

(1S,4aR)-3-acetyl-4a-{[(2S,4R,5S,6R)-4,5-dihydroxy-6-methyloxan-2-yl]oxy}-4,6,7,9-tetrahydroxy-1-methoxy-1,2,4a,5,12,12a-hexahydrotetracene-2,5-dione belongs to the class of organic compounds known as o-glycosyl compounds. These are glycoside in which a sugar group is bonded through one carbon to another group via a O-glycosidic bond. (1s,4ar)-3-acetyl-4a-{[(2s,4r,5s,6r)-4,5-dihydroxy-6-methyloxan-2-yl]oxy}-4,6,7,9-tetrahydroxy-1-methoxy-12,12a-dihydro-1h-tetracene-2,5-dione is found in Streptomyces argillaceus. Based on a literature review very few articles have been published on (1S,4aR)-3-acetyl-4a-{[(2S,4R,5S,6R)-4,5-dihydroxy-6-methyloxan-2-yl]oxy}-4,6,7,9-tetrahydroxy-1-methoxy-1,2,4a,5,12,12a-hexahydrotetracene-2,5-dione.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309102200132D          

 39 43  0  0  1  0            999 V2000
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 O   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


  Mrv1652309102200132D          

 39 43  0  0  1  0            999 V2000
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  1  2  1  0  0  0  0
  3  2  1  1  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4  6  1  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
  6 10  2  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
 12 13  1  1  0  0  0
 14 13  1  1  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  1  0  0  0
 16 18  1  0  0  0  0
 18 19  1  6  0  0  0
 18 20  1  0  0  0  0
 20 21  1  1  0  0  0
 20 22  1  0  0  0  0
 14 22  1  0  0  0  0
 12 23  1  0  0  0  0
 23 24  2  0  0  0  0
 23 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 30 31  1  0  0  0  0
 30 32  1  0  0  0  0
 32 33  2  0  0  0  0
 33 34  1  0  0  0  0
 33 35  1  0  0  0  0
 28 35  1  0  0  0  0
 35 36  2  0  0  0  0
 25 36  1  0  0  0  0
 36 37  1  0  0  0  0
 26 38  1  0  0  0  0
 38 39  1  0  0  0  0
  3 39  1  0  0  0  0
 12 39  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0291216

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CO[C@H]1C2CC3=C(C(O)=C4C(O)=CC(O)=CC4=C3)C(=O)[C@]2(O[C@H]2C[C@@H](O)[C@H](O)[C@@H](C)O2)C(O)=C(C(C)=O)C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C27H28O12/c1-9(28)18-23(34)24(37-3)14-6-12-4-11-5-13(29)7-15(30)19(11)22(33)20(12)26(36)27(14,25(18)35)39-17-8-16(31)21(32)10(2)38-17/h4-5,7,10,14,16-17,21,24,29-33,35H,6,8H2,1-3H3/t10-,14?,16-,17+,21-,24+,27-/m1/s1

> <INCHI_KEY>
NROOIKAJMQWERE-XARGASECSA-N

> <FORMULA>
C27H28O12

> <MOLECULAR_WEIGHT>
544.509

> <EXACT_MASS>
544.158076342

> <JCHEM_ACCEPTOR_COUNT>
12

> <JCHEM_ATOM_COUNT>
67

> <JCHEM_AVERAGE_POLARIZABILITY>
53.95846928330201

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,4aR)-3-acetyl-4a-{[(2S,4R,5S,6R)-4,5-dihydroxy-6-methyloxan-2-yl]oxy}-4,6,7,9-tetrahydroxy-1-methoxy-1,2,4a,5,12,12a-hexahydrotetracene-2,5-dione

> <JCHEM_LOGP>
1.6508080393333326

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
7.732956712593055

> <JCHEM_PKA_STRONGEST_ACIDIC>
0.828209664260279

> <JCHEM_PKA_STRONGEST_BASIC>
-3.25259197802721

> <JCHEM_POLAR_SURFACE_AREA>
200.28

> <JCHEM_REFRACTIVITY>
133.32139999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(1S,4aR)-3-acetyl-4a-{[(2S,4R,5S,6R)-4,5-dihydroxy-6-methyloxan-2-yl]oxy}-4,6,7,9-tetrahydroxy-1-methoxy-12,12a-dihydro-1H-tetracene-2,5-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 10-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-SEP-22         0                                  
HETATM    1  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       5.335  -3.080   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.667  -7.700   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       2.498  -8.609   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       5.335  -7.700   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       4.430  -8.946   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       6.668  -6.930   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       6.668  -8.470   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       5.335  -9.240   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.335 -10.780   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.001 -11.550   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       4.001 -13.090   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       2.667 -10.780   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       1.334 -11.550   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       2.667  -9.240   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       1.334  -8.470   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       4.001  -8.470   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       8.002  -7.700   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       8.002  -9.240   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       9.336  -6.930   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       9.336  -5.390   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      10.669  -4.620   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      12.003  -5.390   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      13.337  -4.620   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      14.670  -5.390   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      16.004  -4.620   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      14.670  -6.930   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      13.337  -7.700   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      13.337  -9.240   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0      12.003  -6.930   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      10.669  -7.700   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0      10.669  -9.240   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0       8.002  -4.620   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       6.668  -5.390   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   39                                                  
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7   10                                                  
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7                                                            
CONECT   10    6   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13   23   39                                             
CONECT   13   12   14                                                       
CONECT   14   13   15   22                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   14                                                       
CONECT   23   12   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26   36                                                  
CONECT   26   25   27   38                                                  
CONECT   27   26   28                                                       
CONECT   28   27   29   35                                                  
CONECT   29   28   30                                                       
CONECT   30   29   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30   33                                                       
CONECT   33   32   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33   28   36                                                  
CONECT   36   35   25   37                                                  
CONECT   37   36                                                            
CONECT   38   26   39                                                       
CONECT   39   38    3   12                                                  
MASTER        0    0    0    0    0    0    0    0   39    0   86    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₇H₂₈O₁₂

Average Mass

544.5090 Da

Monoisotopic Mass

544.15808 Da

IUPAC Name

(1S,4aR)-3-acetyl-4a-{[(2S,4R,5S,6R)-4,5-dihydroxy-6-methyloxan-2-yl]oxy}-4,6,7,9-tetrahydroxy-1-methoxy-1,2,4a,5,12,12a-hexahydrotetracene-2,5-dione

Traditional Name

(1S,4aR)-3-acetyl-4a-{[(2S,4R,5S,6R)-4,5-dihydroxy-6-methyloxan-2-yl]oxy}-4,6,7,9-tetrahydroxy-1-methoxy-12,12a-dihydro-1H-tetracene-2,5-dione

CAS Registry Number

Not Available

SMILES

CO[C@H]1C2CC3=C(C(O)=C4C(O)=CC(O)=CC4=C3)C(=O)[C@]2(O[C@H]2C[C@@H](O)[C@H](O)[C@@H](C)O2)C(O)=C(C(C)=O)C1=O

InChI Identifier

InChI=1S/C27H28O12/c1-9(28)18-23(34)24(37-3)14-6-12-4-11-5-13(29)7-15(30)19(11)22(33)20(12)26(36)27(14,25(18)35)39-17-8-16(31)21(32)10(2)38-17/h4-5,7,10,14,16-17,21,24,29-33,35H,6,8H2,1-3H3/t10-,14?,16-,17+,21-,24+,27-/m1/s1

InChI Key

NROOIKAJMQWERE-XARGASECSA-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 argillaceus	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as o-glycosyl compounds. These are glycoside in which a sugar group is bonded through one carbon to another group via a O-glycosidic bond.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

O-glycosyl compounds

Alternative Parents

Substituents

Hexose monosaccharide
O-glycosyl compound
1-naphthol
2-naphthol
Tetralin
Naphthalene
Aryl alkyl ketone
Aryl ketone
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Cyclohexenone
Benzenoid
Oxane
Monosaccharide
Vinylogous acid
Cyclic ketone
Secondary alcohol
Ketone
1,2-diol
Oxacycle
Organoheterocyclic compound
Polyol
Ether
Enol
Dialkyl ether
Acetal
Organic oxide
Hydrocarbon derivative
Carbonyl group
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	1.65	ChemAxon
pKa (Strongest Acidic)	0.83	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	12	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	200.28 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	133.32 m³·mol⁻¹	ChemAxon
Polarizability	53.96 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	No	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

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

163056982

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1s,4ar)-3-acetyl-4a-{[(2s,4r,5s,6r)-4,5-dihydroxy-6-methyloxan-2-yl]oxy}-4,6,7,9-tetrahydroxy-1-methoxy-12,12a-dihydro-1h-tetracene-2,5-dione (NP0291216)

MOL for NP0291216 ((1s,4ar)-3-acetyl-4a-{[(2s,4r,5s,6r)-4,5-dihydroxy-6-methyloxan-2-yl]oxy}-4,6,7,9-tetrahydroxy-1-methoxy-12,12a-dihydro-1h-tetracene-2,5-dione)

3D MOL for NP0291216 ((1s,4ar)-3-acetyl-4a-{[(2s,4r,5s,6r)-4,5-dihydroxy-6-methyloxan-2-yl]oxy}-4,6,7,9-tetrahydroxy-1-methoxy-12,12a-dihydro-1h-tetracene-2,5-dione)

3D SDF for NP0291216 ((1s,4ar)-3-acetyl-4a-{[(2s,4r,5s,6r)-4,5-dihydroxy-6-methyloxan-2-yl]oxy}-4,6,7,9-tetrahydroxy-1-methoxy-12,12a-dihydro-1h-tetracene-2,5-dione)

3D-SDF for NP0291216 ((1s,4ar)-3-acetyl-4a-{[(2s,4r,5s,6r)-4,5-dihydroxy-6-methyloxan-2-yl]oxy}-4,6,7,9-tetrahydroxy-1-methoxy-12,12a-dihydro-1h-tetracene-2,5-dione)

PDB for NP0291216 ((1s,4ar)-3-acetyl-4a-{[(2s,4r,5s,6r)-4,5-dihydroxy-6-methyloxan-2-yl]oxy}-4,6,7,9-tetrahydroxy-1-methoxy-12,12a-dihydro-1h-tetracene-2,5-dione)

3D PDB for NP0291216 ((1s,4ar)-3-acetyl-4a-{[(2s,4r,5s,6r)-4,5-dihydroxy-6-methyloxan-2-yl]oxy}-4,6,7,9-tetrahydroxy-1-methoxy-12,12a-dihydro-1h-tetracene-2,5-dione)

SMILES for NP0291216 ((1s,4ar)-3-acetyl-4a-{[(2s,4r,5s,6r)-4,5-dihydroxy-6-methyloxan-2-yl]oxy}-4,6,7,9-tetrahydroxy-1-methoxy-12,12a-dihydro-1h-tetracene-2,5-dione)

INCHI for NP0291216 ((1s,4ar)-3-acetyl-4a-{[(2s,4r,5s,6r)-4,5-dihydroxy-6-methyloxan-2-yl]oxy}-4,6,7,9-tetrahydroxy-1-methoxy-12,12a-dihydro-1h-tetracene-2,5-dione)

Structure for NP0291216 ((1s,4ar)-3-acetyl-4a-{[(2s,4r,5s,6r)-4,5-dihydroxy-6-methyloxan-2-yl]oxy}-4,6,7,9-tetrahydroxy-1-methoxy-12,12a-dihydro-1h-tetracene-2,5-dione)

3D Structure for NP0291216 ((1s,4ar)-3-acetyl-4a-{[(2s,4r,5s,6r)-4,5-dihydroxy-6-methyloxan-2-yl]oxy}-4,6,7,9-tetrahydroxy-1-methoxy-12,12a-dihydro-1h-tetracene-2,5-dione)