NP-MRD: Showing NP-Card for Tuberosinone (NP0069359)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-04-28 14:42:44 UTC

Updated at

2022-04-28 14:42:44 UTC

NP-MRD ID

NP0069359

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Tuberosinone

Description

17-Hydroxy-3,5-dioxa-11-azapentacyclo[10.7.1.0²,⁶.0⁸,²⁰.0¹⁴,¹⁹]Icosa-1(19),2(6),7,12(20),13,15,17-heptaene-9,10-dione belongs to the class of organic compounds known as 4,5-dioxoaporphines. These are alkaloids that contains the tetracyclic aporphine skeleton with two C=O groups at the 4- and 5-positions. Tuberosinone is found in Aristolochia cinnabarina, Aristolochia kaempferi and Aristolochia tuberosa. 17-Hydroxy-3,5-dioxa-11-azapentacyclo[10.7.1.0²,⁶.0⁸,²⁰.0¹⁴,¹⁹]Icosa-1(19),2(6),7,12(20),13,15,17-heptaene-9,10-dione is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 32 36  0  0  0  0  0  0  0  0999 V2000
   -5.0872   -1.8208   -0.0257 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9289   -1.3478    0.0003 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7560   -2.1378    0.0250 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4538   -1.5789    0.0543 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3283   -2.3811    0.0780 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9146   -1.8028    0.1059 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9873   -2.6506    0.1284 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2766   -2.1631    0.1573 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4335   -0.8041    0.1624 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7473   -0.2983    0.1918 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3807    0.0960    0.1404 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1025   -0.4133    0.1118 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0391    0.3655    0.0877 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0931    1.7427    0.0923 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0181    2.5892    0.0689 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2468    2.0119    0.0413 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3967    0.6369    0.0363 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3084   -0.2083    0.0591 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7646    0.0779    0.0056 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7195    0.8727   -0.0143 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5401    3.8960    0.0810 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8212    3.8276   -0.3374 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2343    2.5301    0.1183 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8489   -3.1798    0.0217 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4858   -3.4511    0.0732 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8746   -3.7421    0.1246 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1183   -2.8605    0.1749 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2619   -0.1063   -0.6429 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6060    1.1332    0.1466 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1163    2.6496    0.0230 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8146    3.8837   -1.4443 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3722    4.6335    0.1545 H   0  0  0  0  0  0  0  0  0  0  0  0
 10  9  1  0
  9  8  2  0
  8  7  1  0
  7  6  2  0
  6  5  1  0
  5  4  2  0
  4  3  1  0
  3  2  1  0
  2  1  2  0
  2 19  1  0
 19 20  2  0
 19 17  1  0
 17 18  1  0
 18 13  2  0
 13 14  1  0
 14 23  1  0
 23 22  1  0
 22 21  1  0
 21 15  1  0
 15 16  1  0
 13 12  1  0
 12 11  2  0
 11  9  1  0
 12  6  1  0
 18  4  1  0
 15 14  2  0
 16 17  2  0
 10 28  1  0
  8 27  1  0
  7 26  1  0
  5 25  1  0
  3 24  1  0
 22 31  1  0
 22 32  1  0
 16 30  1  0
 11 29  1  0
M  END


  Mrv1533005011514092D          

 23 27  0  0  0  0            999 V2000
    5.7158    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3149    2.0445    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1354    2.1307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4710    1.3770    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 15 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
  5 21  1  0  0  0  0
 21 22  2  0  0  0  0
  2 22  1  0  0  0  0
 20 23  1  0  0  0  0
  7 23  1  0  0  0  0
 13 23  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0069359

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC1=CC=C2C=C3NC(=O)C(=O)C4=C3C(=C3OCOC3=C4)C2=C1

> <INCHI_IDENTIFIER>
InChI=1S/C17H9NO5/c19-8-2-1-7-3-11-13-10(15(20)17(21)18-11)5-12-16(23-6-22-12)14(13)9(7)4-8/h1-5,19H,6H2,(H,18,21)

> <INCHI_KEY>
QTUOOWLAKCKQHG-UHFFFAOYSA-N

> <FORMULA>
C17H9NO5

> <MOLECULAR_WEIGHT>
307.261

> <EXACT_MASS>
307.048072394

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
32

> <JCHEM_AVERAGE_POLARIZABILITY>
29.869986897233368

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
17-hydroxy-3,5-dioxa-11-azapentacyclo[10.7.1.0²,⁶.0⁸,²⁰.0¹⁴,¹⁹]icosa-1,6,8(20),12,14,16,18-heptaene-9,10-dione

> <ALOGPS_LOGP>
2.19

> <JCHEM_LOGP>
2.250165220666667

> <ALOGPS_LOGS>
-3.22

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.603157743728204

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.996737898603461

> <JCHEM_PKA_STRONGEST_BASIC>
-4.673369093848972

> <JCHEM_POLAR_SURFACE_AREA>
84.86000000000001

> <JCHEM_REFRACTIVITY>
81.1232

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.84e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
17-hydroxy-3,5-dioxa-11-azapentacyclo[10.7.1.0²,⁶.0⁸,²⁰.0¹⁴,¹⁹]icosa-1,6,8(20),12,14,16,18-heptaene-9,10-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 01-MAY-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   01-MAY-15         0                                  
HETATM    1  O   UNK     0      10.669   0.000   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       9.336  -2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.002  -3.080   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM    8  N   UNK     0       2.667  -3.080   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       0.000  -3.080   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       4.321   3.816   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       5.853   3.977   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       6.479   2.570   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.335  -0.000   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       8.002  -0.000   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   22                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   21                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   23                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   23                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   19                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   15   20                                                  
CONECT   20   19   21   23                                                  
CONECT   21   20    5   22                                                  
CONECT   22   21    2                                                       
CONECT   23   20    7   13                                                  
MASTER        0    0    0    0    0    0    0    0   23    0   54    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₇H₉NO₅

Average Mass

307.2610 Da

Monoisotopic Mass

307.04807 Da

IUPAC Name

17-hydroxy-3,5-dioxa-11-azapentacyclo[10.7.1.0²,⁶.0⁸,²⁰.0¹⁴,¹⁹]icosa-1,6,8(20),12,14,16,18-heptaene-9,10-dione

Traditional Name

17-hydroxy-3,5-dioxa-11-azapentacyclo[10.7.1.0²,⁶.0⁸,²⁰.0¹⁴,¹⁹]icosa-1,6,8(20),12,14,16,18-heptaene-9,10-dione

CAS Registry Number

Not Available

SMILES

OC1=CC=C2C=C3NC(=O)C(=O)C4=C3C(=C3OCOC3=C4)C2=C1

InChI Identifier

InChI=1S/C17H9NO5/c19-8-2-1-7-3-11-13-10(15(20)17(21)18-11)5-12-16(23-6-22-12)14(13)9(7)4-8/h1-5,19H,6H2,(H,18,21)

InChI Key

QTUOOWLAKCKQHG-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, 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
Aristolochia cinnabarina	Plant	KNApSAcK
Aristolochia kaempferi	LOTUS Database	35616633
Aristolochia tuberosa	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 4,5-dioxoaporphines. These are alkaloids that contains the tetracyclic aporphine skeleton with two C=O groups at the 4- and 5-positions.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Aporphines

Sub Class

4,5-dioxoaporphines

Direct Parent

4,5-dioxoaporphines

Alternative Parents

Substituents

4,5-dioxoaporphine
Phenanthrol
Benzoquinoline
Phenanthrene
Isoquinolone
2-naphthol
Quinolone
Quinoline
Naphthalene
Benzodioxole
Aryl ketone
1-hydroxy-2-unsubstituted benzenoid
Benzenoid
Secondary carboxylic acid amide
Carboxamide group
Ketone
Lactam
Azacycle
Organoheterocyclic compound
Oxacycle
Carboxylic acid derivative
Acetal
Organic oxide
Aldehyde
Organonitrogen compound
Organooxygen compound
Organic oxygen compound
Carbonyl group
Organic nitrogen compound
Organopnictogen compound
Hydrocarbon derivative
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	2.19	ALOGPS
logP	2.25	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	9	ChemAxon
pKa (Strongest Basic)	-4.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	84.86 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	81.12 m³·mol⁻¹	ChemAxon
Polarizability	29.87 Å³	ChemAxon
Number of Rings	5	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

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

101674012

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Tuberosinone (NP0069359)

MOL for NP0069359 (Tuberosinone)

3D MOL for NP0069359 (Tuberosinone)

3D SDF for NP0069359 (Tuberosinone)

3D-SDF for NP0069359 (Tuberosinone)

PDB for NP0069359 (Tuberosinone)

3D PDB for NP0069359 (Tuberosinone)

SMILES for NP0069359 (Tuberosinone)

INCHI for NP0069359 (Tuberosinone)

Structure for NP0069359 (Tuberosinone)

3D Structure for NP0069359 (Tuberosinone)