NP-MRD: Showing NP-Card for (8s,10s)-10-{[(2r,4s,5s,6s)-4-amino-5-hydroxy-6-methyloxan-2-yl]oxy}-8-ethyl-8,11-dihydroxy-1-methoxy-9,10-dihydro-7h-tetracene-5,12-dione (NP0174748)

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Record Information

Version

2.0

Created at

2022-09-03 12:03:32 UTC

Updated at

2022-09-03 12:03:32 UTC

NP-MRD ID

NP0174748

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(8s,10s)-10-{[(2r,4s,5s,6s)-4-amino-5-hydroxy-6-methyloxan-2-yl]oxy}-8-ethyl-8,11-dihydroxy-1-methoxy-9,10-dihydro-7h-tetracene-5,12-dione

Description

11-Deoxy-13-deoxodaunorubicin 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. Based on a literature review very few articles have been published on 11-Deoxy-13-deoxodaunorubicin.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309032214032D          

 36 40  0  0  1  0            999 V2000
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    3.5724    1.2375    0.0000 C   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


  Mrv1652309032214032D          

 36 40  0  0  1  0            999 V2000
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M  END
> <DATABASE_ID>
NP0174748

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC[C@@]1(O)C[C@H](O[C@H]2C[C@H](N)[C@H](O)[C@H](C)O2)C2=C(O)C3=C(C=C2C1)C(=O)C1=CC=CC(OC)=C1C3=O

> <INCHI_IDENTIFIER>
InChI=1S/C27H31NO8/c1-4-27(33)10-13-8-15-22(26(32)21-14(24(15)30)6-5-7-17(21)34-3)25(31)20(13)18(11-27)36-19-9-16(28)23(29)12(2)35-19/h5-8,12,16,18-19,23,29,31,33H,4,9-11,28H2,1-3H3/t12-,16-,18-,19-,23+,27-/m0/s1

> <INCHI_KEY>
IYSDLBHEPBYCFI-PAFKHDOYSA-N

> <FORMULA>
C27H31NO8

> <MOLECULAR_WEIGHT>
497.544

> <EXACT_MASS>
497.204966962

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
67

> <JCHEM_AVERAGE_POLARIZABILITY>
52.72704632926629

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(8S,10S)-10-{[(2R,4S,5S,6S)-4-amino-5-hydroxy-6-methyloxan-2-yl]oxy}-8-ethyl-8,11-dihydroxy-1-methoxy-5,7,8,9,10,12-hexahydrotetracene-5,12-dione

> <ALOGPS_LOGP>
1.89

> <JCHEM_LOGP>
1.841364847279981

> <ALOGPS_LOGS>
-3.48

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
13.564762831192574

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.78899263765233

> <JCHEM_PKA_STRONGEST_BASIC>
9.462707829290972

> <JCHEM_POLAR_SURFACE_AREA>
148.54

> <JCHEM_REFRACTIVITY>
130.39729999999992

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.63e-01 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 03-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-SEP-22         0                                  
HETATM    1  C   UNK     0      10.206   4.167   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      11.196   2.987   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      10.669   1.540   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      12.186   1.273   0.000  0.00  0.00           O+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       6.668   2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       6.668  -2.310   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       8.002   0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       9.336  -0.770   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       9.336  -2.310   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      10.669  -3.080   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      12.003  -2.310   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      13.337  -3.080   0.000  0.00  0.00           C+0
HETATM   18  N   UNK     0      14.670  -2.310   0.000  0.00  0.00           N+0
HETATM   19  C   UNK     0      13.337  -4.620   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      14.670  -5.390   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      12.003  -5.390   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      12.003  -6.930   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      10.669  -4.620   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      10.669  -0.000   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       4.001  -2.310   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -0.000   0.000   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0       4.001   3.850   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5   24                                             
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7   12                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   35                                                  
CONECT    9    8   10   25                                                  
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10    6   13                                                  
CONECT   13   12   14   24                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   23                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   15                                                       
CONECT   24   13    3                                                       
CONECT   25    9   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28   34                                                  
CONECT   28   27   29   31                                                  
CONECT   29   28   30                                                       
CONECT   30   29                                                            
CONECT   31   28   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33   27   35                                                  
CONECT   35   34    8   36                                                  
CONECT   36   35                                                            
MASTER        0    0    0    0    0    0    0    0   36    0   80    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₇H₃₁NO₈

Average Mass

497.5440 Da

Monoisotopic Mass

497.20497 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

CC[C@@]1(O)C[C@H](O[C@H]2C[C@H](N)[C@H](O)[C@H](C)O2)C2=C(O)C3=C(C=C2C1)C(=O)C1=CC=CC(OC)=C1C3=O

InChI Identifier

InChI=1S/C27H31NO8/c1-4-27(33)10-13-8-15-22(26(32)21-14(24(15)30)6-5-7-17(21)34-3)25(31)20(13)18(11-27)36-19-9-16(28)23(29)12(2)35-19/h5-8,12,16,18-19,23,29,31,33H,4,9-11,28H2,1-3H3/t12-,16-,18-,19-,23+,27-/m0/s1

InChI Key

IYSDLBHEPBYCFI-PAFKHDOYSA-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

Not Available

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

Anthracycline
Anthracyclinone-skeleton
Aminoglycoside core
Tetracenequinone
9,10-anthraquinone
1,4-anthraquinone
Anthracene
Hexose monosaccharide
Glycosyl compound
O-glycosyl compound
Tetralin
Aryl ketone
Anisole
Amino saccharide
Alkyl aryl ether
1-hydroxy-4-unsubstituted benzenoid
Benzenoid
Oxane
Monosaccharide
Vinylogous acid
Tertiary alcohol
Secondary alcohol
1,2-aminoalcohol
Ketone
Oxacycle
Organoheterocyclic compound
Ether
Acetal
Primary aliphatic amine
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic oxygen compound
Organonitrogen compound
Organooxygen compound
Organic nitrogen compound
Amine
Primary amine
Aldehyde
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	1.89	ALOGPS
logS	-3.5	ALOGPS

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

102115576

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (8s,10s)-10-{[(2r,4s,5s,6s)-4-amino-5-hydroxy-6-methyloxan-2-yl]oxy}-8-ethyl-8,11-dihydroxy-1-methoxy-9,10-dihydro-7h-tetracene-5,12-dione (NP0174748)

MOL for NP0174748 ((8s,10s)-10-{[(2r,4s,5s,6s)-4-amino-5-hydroxy-6-methyloxan-2-yl]oxy}-8-ethyl-8,11-dihydroxy-1-methoxy-9,10-dihydro-7h-tetracene-5,12-dione)

3D MOL for NP0174748 ((8s,10s)-10-{[(2r,4s,5s,6s)-4-amino-5-hydroxy-6-methyloxan-2-yl]oxy}-8-ethyl-8,11-dihydroxy-1-methoxy-9,10-dihydro-7h-tetracene-5,12-dione)

3D SDF for NP0174748 ((8s,10s)-10-{[(2r,4s,5s,6s)-4-amino-5-hydroxy-6-methyloxan-2-yl]oxy}-8-ethyl-8,11-dihydroxy-1-methoxy-9,10-dihydro-7h-tetracene-5,12-dione)

3D-SDF for NP0174748 ((8s,10s)-10-{[(2r,4s,5s,6s)-4-amino-5-hydroxy-6-methyloxan-2-yl]oxy}-8-ethyl-8,11-dihydroxy-1-methoxy-9,10-dihydro-7h-tetracene-5,12-dione)

PDB for NP0174748 ((8s,10s)-10-{[(2r,4s,5s,6s)-4-amino-5-hydroxy-6-methyloxan-2-yl]oxy}-8-ethyl-8,11-dihydroxy-1-methoxy-9,10-dihydro-7h-tetracene-5,12-dione)

3D PDB for NP0174748 ((8s,10s)-10-{[(2r,4s,5s,6s)-4-amino-5-hydroxy-6-methyloxan-2-yl]oxy}-8-ethyl-8,11-dihydroxy-1-methoxy-9,10-dihydro-7h-tetracene-5,12-dione)

SMILES for NP0174748 ((8s,10s)-10-{[(2r,4s,5s,6s)-4-amino-5-hydroxy-6-methyloxan-2-yl]oxy}-8-ethyl-8,11-dihydroxy-1-methoxy-9,10-dihydro-7h-tetracene-5,12-dione)

INCHI for NP0174748 ((8s,10s)-10-{[(2r,4s,5s,6s)-4-amino-5-hydroxy-6-methyloxan-2-yl]oxy}-8-ethyl-8,11-dihydroxy-1-methoxy-9,10-dihydro-7h-tetracene-5,12-dione)

Structure for NP0174748 ((8s,10s)-10-{[(2r,4s,5s,6s)-4-amino-5-hydroxy-6-methyloxan-2-yl]oxy}-8-ethyl-8,11-dihydroxy-1-methoxy-9,10-dihydro-7h-tetracene-5,12-dione)

3D Structure for NP0174748 ((8s,10s)-10-{[(2r,4s,5s,6s)-4-amino-5-hydroxy-6-methyloxan-2-yl]oxy}-8-ethyl-8,11-dihydroxy-1-methoxy-9,10-dihydro-7h-tetracene-5,12-dione)