NP-MRD: Showing NP-Card for 5-hydroxy-6-[(2r,4r,5s,6r)-5-hydroxy-6-methyl-4-(methylamino)oxan-2-yl]-1-[(1r)-1-hydroxyethyl]-3-methylnaphtho[2,3-c]thiophene-4,9-dione (NP0260767)

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Record Information

Version

2.0

Created at

2022-09-08 03:01:25 UTC

Updated at

2022-09-08 03:01:25 UTC

NP-MRD ID

NP0260767

Secondary Accession Numbers

None

Natural Product Identification

Common Name

5-hydroxy-6-[(2r,4r,5s,6r)-5-hydroxy-6-methyl-4-(methylamino)oxan-2-yl]-1-[(1r)-1-hydroxyethyl]-3-methylnaphtho[2,3-c]thiophene-4,9-dione

Description

Thioquinomycin C belongs to the class of organic compounds known as naphthalenes. Naphthalenes are compounds containing a naphthalene moiety, which consists of two fused benzene rings. Based on a literature review very few articles have been published on Thioquinomycin C.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309082205012D          

 30 33  0  0  1  0            999 V2000
    6.9246   -1.7771    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2102   -1.3646    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.2102   -0.5396    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.4957   -0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4957    0.6979    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.7812    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668    0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668   -0.1271    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -0.1271    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    0.8555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8838    0.0709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538    1.5229    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    2.1904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8838    2.9750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0768    3.1465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4358    3.5881    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    3.1729    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2102    1.1104    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9246    0.6979    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.6391    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9246   -0.1271    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.6391   -0.5396    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  3  2  1  6  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  6  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
  6 11  1  0  0  0  0
 11 12  1  0  0  0  0
 10 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  1  1  0  0  0
 19 23  2  0  0  0  0
 15 23  1  0  0  0  0
 23 24  1  0  0  0  0
  9 24  1  0  0  0  0
 24 25  2  0  0  0  0
  5 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  6  0  0  0
 27 29  1  0  0  0  0
  3 29  1  0  0  0  0
 29 30  1  1  0  0  0
M  END


  Mrv1652309082205012D          

 30 33  0  0  1  0            999 V2000
    6.9246   -1.7771    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2102   -1.3646    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.2102   -0.5396    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.4957   -0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4957    0.6979    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.7812    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668    0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668   -0.1271    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -0.1271    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    0.8555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8838    0.0709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538    1.5229    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    2.1904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8838    2.9750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0768    3.1465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4358    3.5881    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    3.1729    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2102    1.1104    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9246    0.6979    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.6391    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9246   -0.1271    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.6391   -0.5396    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  3  2  1  6  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  6  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
  6 11  1  0  0  0  0
 11 12  1  0  0  0  0
 10 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  1  1  0  0  0
 19 23  2  0  0  0  0
 15 23  1  0  0  0  0
 23 24  1  0  0  0  0
  9 24  1  0  0  0  0
 24 25  2  0  0  0  0
  5 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  6  0  0  0
 27 29  1  0  0  0  0
  3 29  1  0  0  0  0
 29 30  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0260767

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CN[C@@H]1C[C@@H](O[C@H](C)[C@H]1O)C1=CC=C2C(=O)C3=C(SC(C)=C3C(=O)C2=C1O)[C@@H](C)O

> <INCHI_IDENTIFIER>
InChI=1S/C22H25NO6S/c1-8(24)22-17-15(10(3)30-22)21(28)16-12(20(17)27)6-5-11(19(16)26)14-7-13(23-4)18(25)9(2)29-14/h5-6,8-9,13-14,18,23-26H,7H2,1-4H3/t8-,9-,13-,14-,18-/m1/s1

> <INCHI_KEY>
JGHOHVUBTOPRAL-XKBPWBJDSA-N

> <FORMULA>
C22H25NO6S

> <MOLECULAR_WEIGHT>
431.5

> <EXACT_MASS>
431.140258703

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
55

> <JCHEM_AVERAGE_POLARIZABILITY>
44.63036798470064

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5-hydroxy-6-[(2R,4R,5S,6R)-5-hydroxy-6-methyl-4-(methylamino)oxan-2-yl]-1-[(1R)-1-hydroxyethyl]-3-methyl-4H,9H-naphtho[2,3-c]thiophene-4,9-dione

> <JCHEM_LOGP>
1.6988239474802491

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
13.409673314362575

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.711628518966756

> <JCHEM_PKA_STRONGEST_BASIC>
9.350107391445055

> <JCHEM_POLAR_SURFACE_AREA>
116.08999999999999

> <JCHEM_REFRACTIVITY>
113.22239999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
5-hydroxy-6-[(2R,4R,5S,6R)-5-hydroxy-6-methyl-4-(methylamino)oxan-2-yl]-1-[(1R)-1-hydroxyethyl]-3-methylnaphtho[2,3-c]thiophene-4,9-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 08-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   08-SEP-22         0                                  
HETATM    1  C   UNK     0      12.926  -3.317   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0      11.592  -2.547   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0      11.592  -1.007   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      10.259  -0.237   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      10.259   1.303   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.925   2.073   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.925   3.613   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.591   4.383   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.258   3.613   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.258   2.073   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.591   1.303   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       7.591  -0.237   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       4.924   1.303   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       4.924  -0.237   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       3.590   2.073   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.126   1.597   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.650   0.132   0.000  0.00  0.00           C+0
HETATM   18  S   UNK     0       1.220   2.843   0.000  0.00  0.00           S+0
HETATM   19  C   UNK     0       2.126   4.089   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.650   5.553   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       0.143   5.874   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       2.680   6.698   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       3.590   3.613   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       4.924   4.383   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       4.924   5.923   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0      11.592   2.073   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      12.926   1.303   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      14.260   2.073   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      12.926  -0.237   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      14.260  -1.007   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   29                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   26                                                  
CONECT    6    5    7   11                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   24                                                  
CONECT   10    9   11   13                                                  
CONECT   11   10    6   12                                                  
CONECT   12   11                                                            
CONECT   13   10   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16   23                                                  
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19                                                       
CONECT   19   18   20   23                                                  
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20                                                            
CONECT   23   19   15   24                                                  
CONECT   24   23    9   25                                                  
CONECT   25   24                                                            
CONECT   26    5   27                                                       
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27    3   30                                                  
CONECT   30   29                                                            
MASTER        0    0    0    0    0    0    0    0   30    0   66    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₂H₂₅NO₆S

Average Mass

431.5000 Da

Monoisotopic Mass

431.14026 Da

IUPAC Name

5-hydroxy-6-[(2R,4R,5S,6R)-5-hydroxy-6-methyl-4-(methylamino)oxan-2-yl]-1-[(1R)-1-hydroxyethyl]-3-methyl-4H,9H-naphtho[2,3-c]thiophene-4,9-dione

Traditional Name

5-hydroxy-6-[(2R,4R,5S,6R)-5-hydroxy-6-methyl-4-(methylamino)oxan-2-yl]-1-[(1R)-1-hydroxyethyl]-3-methylnaphtho[2,3-c]thiophene-4,9-dione

CAS Registry Number

Not Available

SMILES

CN[C@@H]1C[C@@H](O[C@H](C)[C@H]1O)C1=CC=C2C(=O)C3=C(SC(C)=C3C(=O)C2=C1O)[C@@H](C)O

InChI Identifier

InChI=1S/C22H25NO6S/c1-8(24)22-17-15(10(3)30-22)21(28)16-12(20(17)27)6-5-11(19(16)26)14-7-13(23-4)18(25)9(2)29-14/h5-6,8-9,13-14,18,23-26H,7H2,1-4H3/t8-,9-,13-,14-,18-/m1/s1

InChI Key

JGHOHVUBTOPRAL-XKBPWBJDSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as naphthalenes. Naphthalenes are compounds containing a naphthalene moiety, which consists of two fused benzene rings.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Naphthalenes

Sub Class

Not Available

Direct Parent

Naphthalenes

Alternative Parents

Substituents

Naphthalene
Aryl ketone
1-hydroxy-4-unsubstituted benzenoid
Aralkylamine
Oxane
Heteroaromatic compound
Vinylogous acid
Thiophene
Secondary alcohol
Ketone
1,2-aminoalcohol
Oxacycle
Organoheterocyclic compound
Secondary amine
Ether
Secondary aliphatic amine
Dialkyl ether
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Aromatic alcohol
Organooxygen compound
Organonitrogen compound
Amine
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	1.7	ChemAxon
pKa (Strongest Acidic)	7.71	ChemAxon
pKa (Strongest Basic)	9.35	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	116.09 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	113.22 m³·mol⁻¹	ChemAxon
Polarizability	44.63 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	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

71048637

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

139590304

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 5-hydroxy-6-[(2r,4r,5s,6r)-5-hydroxy-6-methyl-4-(methylamino)oxan-2-yl]-1-[(1r)-1-hydroxyethyl]-3-methylnaphtho[2,3-c]thiophene-4,9-dione (NP0260767)

MOL for NP0260767 (5-hydroxy-6-[(2r,4r,5s,6r)-5-hydroxy-6-methyl-4-(methylamino)oxan-2-yl]-1-[(1r)-1-hydroxyethyl]-3-methylnaphtho[2,3-c]thiophene-4,9-dione)

3D MOL for NP0260767 (5-hydroxy-6-[(2r,4r,5s,6r)-5-hydroxy-6-methyl-4-(methylamino)oxan-2-yl]-1-[(1r)-1-hydroxyethyl]-3-methylnaphtho[2,3-c]thiophene-4,9-dione)

3D SDF for NP0260767 (5-hydroxy-6-[(2r,4r,5s,6r)-5-hydroxy-6-methyl-4-(methylamino)oxan-2-yl]-1-[(1r)-1-hydroxyethyl]-3-methylnaphtho[2,3-c]thiophene-4,9-dione)

3D-SDF for NP0260767 (5-hydroxy-6-[(2r,4r,5s,6r)-5-hydroxy-6-methyl-4-(methylamino)oxan-2-yl]-1-[(1r)-1-hydroxyethyl]-3-methylnaphtho[2,3-c]thiophene-4,9-dione)

PDB for NP0260767 (5-hydroxy-6-[(2r,4r,5s,6r)-5-hydroxy-6-methyl-4-(methylamino)oxan-2-yl]-1-[(1r)-1-hydroxyethyl]-3-methylnaphtho[2,3-c]thiophene-4,9-dione)

3D PDB for NP0260767 (5-hydroxy-6-[(2r,4r,5s,6r)-5-hydroxy-6-methyl-4-(methylamino)oxan-2-yl]-1-[(1r)-1-hydroxyethyl]-3-methylnaphtho[2,3-c]thiophene-4,9-dione)

SMILES for NP0260767 (5-hydroxy-6-[(2r,4r,5s,6r)-5-hydroxy-6-methyl-4-(methylamino)oxan-2-yl]-1-[(1r)-1-hydroxyethyl]-3-methylnaphtho[2,3-c]thiophene-4,9-dione)

INCHI for NP0260767 (5-hydroxy-6-[(2r,4r,5s,6r)-5-hydroxy-6-methyl-4-(methylamino)oxan-2-yl]-1-[(1r)-1-hydroxyethyl]-3-methylnaphtho[2,3-c]thiophene-4,9-dione)

Structure for NP0260767 (5-hydroxy-6-[(2r,4r,5s,6r)-5-hydroxy-6-methyl-4-(methylamino)oxan-2-yl]-1-[(1r)-1-hydroxyethyl]-3-methylnaphtho[2,3-c]thiophene-4,9-dione)

3D Structure for NP0260767 (5-hydroxy-6-[(2r,4r,5s,6r)-5-hydroxy-6-methyl-4-(methylamino)oxan-2-yl]-1-[(1r)-1-hydroxyethyl]-3-methylnaphtho[2,3-c]thiophene-4,9-dione)