NP-MRD: Showing NP-Card for Steffimycin C (NP0062211)

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Record Information

Version

2.0

Created at

2022-04-28 06:52:04 UTC

Updated at

2022-04-28 06:52:04 UTC

NP-MRD ID

NP0062211

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Steffimycin C

Description

(8R,9R,10S)-1,8,11-trihydroxy-10-{[(2S,3S,4R,5R,6S)-4-hydroxy-3,5-dimethoxy-6-methyloxan-2-yl]oxy}-3,9-dimethoxy-8-methyl-5,7,8,9,10,12-hexahydrotetracene-5,12-dione belongs to the class of organic compounds known as anthracyclines. These are polyketides containing a tetracenequinone ring structure with a sugar attached by glycosidic linkage. Steffimycin C is found in Streptomyces elgrereus. Based on a literature review very few articles have been published on (8R,9R,10S)-1,8,11-trihydroxy-10-{[(2S,3S,4R,5R,6S)-4-hydroxy-3,5-dimethoxy-6-methyloxan-2-yl]oxy}-3,9-dimethoxy-8-methyl-5,7,8,9,10,12-hexahydrotetracene-5,12-dione.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282208522D          

 41 45  0  0  1  0            999 V2000
    5.0013   -1.2375    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


  Mrv1652304282208522D          

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    7.1447   -1.6500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.1447   -2.4750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.4302   -2.8875    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.7158   -2.4750    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.0013   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  2  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
  6 12  1  0  0  0  0
 11 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
 10 17  1  0  0  0  0
 17 18  2  0  0  0  0
 16 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 15 22  1  0  0  0  0
 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
 19 25  1  0  0  0  0
  4 26  1  6  0  0  0
  4 27  1  1  0  0  0
  3 28  1  6  0  0  0
 28 29  1  0  0  0  0
 30  1  1  6  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 30 35  1  0  0  0  0
 35 36  1  6  0  0  0
 36 37  1  0  0  0  0
 34 38  1  1  0  0  0
 33 39  1  6  0  0  0
 39 40  1  0  0  0  0
 32 41  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0062211

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CO[C@H]1[C@H](C)O[C@@H](O[C@@H]2[C@@H](OC)[C@](C)(O)CC3=C2C(O)=C2C(=O)C4=C(C=C(OC)C=C4O)C(=O)C2=C3)[C@@H](OC)[C@@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C29H34O12/c1-11-24(37-4)23(34)26(38-5)28(40-11)41-25-17-12(10-29(2,35)27(25)39-6)7-14-19(21(17)32)22(33)18-15(20(14)31)8-13(36-3)9-16(18)30/h7-9,11,23-28,30,32,34-35H,10H2,1-6H3/t11-,23+,24-,25-,26-,27+,28-,29+/m0/s1

> <INCHI_KEY>
OJEGCXWWBDCZGW-BHPXOZNESA-N

> <FORMULA>
C29H34O12

> <MOLECULAR_WEIGHT>
574.579

> <EXACT_MASS>
574.205026535

> <JCHEM_ACCEPTOR_COUNT>
12

> <JCHEM_ATOM_COUNT>
75

> <JCHEM_AVERAGE_POLARIZABILITY>
58.03811319091531

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(8R,9R,10S)-1,8,11-trihydroxy-10-{[(2S,3S,4R,5R,6S)-4-hydroxy-3,5-dimethoxy-6-methyloxan-2-yl]oxy}-3,9-dimethoxy-8-methyl-5,7,8,9,10,12-hexahydrotetracene-5,12-dione

> <ALOGPS_LOGP>
2.28

> <JCHEM_LOGP>
3.011570591

> <ALOGPS_LOGS>
-3.18

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.321788579127446

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.6101375463978185

> <JCHEM_PKA_STRONGEST_BASIC>
-3.3349853356103942

> <JCHEM_POLAR_SURFACE_AREA>
170.43999999999997

> <JCHEM_REFRACTIVITY>
143.0581

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.80e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(8R,9R,10S)-1,8,11-trihydroxy-10-{[(2S,3S,4R,5R,6S)-4-hydroxy-3,5-dimethoxy-6-methyloxan-2-yl]oxy}-3,9-dimethoxy-8-methyl-9,10-dihydro-7H-tetracene-5,12-dione

> <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  O   UNK     0       9.336  -2.310   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       9.336  -0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      10.669   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      10.669   1.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       9.336   2.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.002  -0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       6.668  -2.310   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       5.335  -0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       4.001   3.850   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       4.001  -2.310   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      -1.334   2.310   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      12.208   1.594   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      11.486   2.846   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0      12.003  -0.770   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      13.337   0.000   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      10.669  -3.080   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      12.003  -2.310   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      13.337  -3.080   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      13.337  -4.620   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      12.003  -5.390   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      10.669  -4.620   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0       9.336  -5.390   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0       8.002  -4.620   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0      12.003  -6.930   0.000  0.00  0.00           O+0
HETATM   39  O   UNK     0      14.670  -5.390   0.000  0.00  0.00           O+0
HETATM   40  C   UNK     0      16.004  -4.620   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      14.670  -2.310   0.000  0.00  0.00           C+0
CONECT    1    2   30                                                       
CONECT    2    1    3    7                                                  
CONECT    3    2    4   28                                                  
CONECT    4    3    5   26   27                                             
CONECT    5    4    6                                                       
CONECT    6    5    7   12                                                  
CONECT    7    6    2    8                                                  
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   17                                                  
CONECT   11   10   12   13                                                  
CONECT   12   11    6                                                       
CONECT   13   11   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16   22                                                  
CONECT   16   15   17   19                                                  
CONECT   17   16   10   18                                                  
CONECT   18   17                                                            
CONECT   19   16   20   25                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21   15                                                       
CONECT   23   21   24                                                       
CONECT   24   23                                                            
CONECT   25   19                                                            
CONECT   26    4                                                            
CONECT   27    4                                                            
CONECT   28    3   29                                                       
CONECT   29   28                                                            
CONECT   30    1   31   35                                                  
CONECT   31   30   32                                                       
CONECT   32   31   33   41                                                  
CONECT   33   32   34   39                                                  
CONECT   34   33   35   38                                                  
CONECT   35   34   30   36                                                  
CONECT   36   35   37                                                       
CONECT   37   36                                                            
CONECT   38   34                                                            
CONECT   39   33   40                                                       
CONECT   40   39                                                            
CONECT   41   32                                                            
MASTER        0    0    0    0    0    0    0    0   41    0   90    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₉H₃₄O₁₂

Average Mass

574.5790 Da

Monoisotopic Mass

574.20503 Da

IUPAC Name

(8R,9R,10S)-1,8,11-trihydroxy-10-{[(2S,3S,4R,5R,6S)-4-hydroxy-3,5-dimethoxy-6-methyloxan-2-yl]oxy}-3,9-dimethoxy-8-methyl-5,7,8,9,10,12-hexahydrotetracene-5,12-dione

Traditional Name

(8R,9R,10S)-1,8,11-trihydroxy-10-{[(2S,3S,4R,5R,6S)-4-hydroxy-3,5-dimethoxy-6-methyloxan-2-yl]oxy}-3,9-dimethoxy-8-methyl-9,10-dihydro-7H-tetracene-5,12-dione

CAS Registry Number

Not Available

SMILES

CO[C@H]1[C@H](C)O[C@@H](O[C@@H]2[C@@H](OC)[C@](C)(O)CC3=C2C(O)=C2C(=O)C4=C(C=C(OC)C=C4O)C(=O)C2=C3)[C@@H](OC)[C@@H]1O

InChI Identifier

InChI=1S/C29H34O12/c1-11-24(37-4)23(34)26(38-5)28(40-11)41-25-17-12(10-29(2,35)27(25)39-6)7-14-19(21(17)32)22(33)18-15(20(14)31)8-13(36-3)9-16(18)30/h7-9,11,23-28,30,32,34-35H,10H2,1-6H3/t11-,23+,24-,25-,26-,27+,28-,29+/m0/s1

InChI Key

OJEGCXWWBDCZGW-BHPXOZNESA-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
Streptomyces elgrereus	Bacteria	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as anthracyclines. These are polyketides containing a tetracenequinone ring structure with a sugar attached by glycosidic linkage.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Anthracyclines

Sub Class

Not Available

Direct Parent

Anthracyclines

Alternative Parents

Substituents

Anthracyclinone-skeleton
Anthracycline
Tetracenequinone
1,4-anthraquinone
9,10-anthraquinone
Anthracene
Hexose monosaccharide
O-glycosyl compound
Glycosyl compound
Tetralin
Aryl ketone
Anisole
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Benzenoid
Oxane
Monosaccharide
Vinylogous acid
Tertiary alcohol
Secondary alcohol
Ketone
Oxacycle
Organoheterocyclic compound
Polyol
Ether
Dialkyl ether
Acetal
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen 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	2.28	ALOGPS
logP	3.01	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	7.61	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	12	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	170.44 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	143.06 m³·mol⁻¹	ChemAxon
Polarizability	58.04 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	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

162870565

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Steffimycin C (NP0062211)

MOL for NP0062211 (Steffimycin C)

3D MOL for NP0062211 (Steffimycin C)

3D SDF for NP0062211 (Steffimycin C)

3D-SDF for NP0062211 (Steffimycin C)

PDB for NP0062211 (Steffimycin C)

3D PDB for NP0062211 (Steffimycin C)

SMILES for NP0062211 (Steffimycin C)

INCHI for NP0062211 (Steffimycin C)

Structure for NP0062211 (Steffimycin C)

3D Structure for NP0062211 (Steffimycin C)