NP-MRD: Showing NP-Card for (1s,2r,7r,14s)-14-hydroxy-12-oxa-6-azatetracyclo[5.5.2.0¹,⁹.0²,⁶]tetradec-9-en-11-one (NP0272547)

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Record Information

Version

2.0

Created at

2022-09-08 19:12:29 UTC

Updated at

2022-09-08 19:12:29 UTC

NP-MRD ID

NP0272547

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,2r,7r,14s)-14-hydroxy-12-oxa-6-azatetracyclo[5.5.2.0¹,⁹.0²,⁶]tetradec-9-en-11-one

Description

(1S,2R,7R,14S)-14-hydroxy-12-oxa-6-azatetracyclo[5.5.2.0¹,⁹.0²,⁶]Tetradec-9-en-11-one belongs to the class of organic compounds known as azaspirodecane derivatives. These are organic compounds containing a spirodecane moiety with at least one nitrogen atom. (1s,2r,7r,14s)-14-hydroxy-12-oxa-6-azatetracyclo[5.5.2.0¹,⁹.0²,⁶]tetradec-9-en-11-one is found in Phyllanthus niruri. Based on a literature review very few articles have been published on (1S,2R,7R,14S)-14-hydroxy-12-oxa-6-azatetracyclo[5.5.2.0¹,⁹.0²,⁶]Tetradec-9-en-11-one.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 31 34  0  0  0  0  0  0  0  0999 V2000
    3.6716   -2.7666    0.1966 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7943   -1.8914    0.0470 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7390   -0.8243   -0.9767 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6674   -0.1046   -0.8089 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0520    1.0590   -1.4672 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2422    1.3025   -0.6610 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2187    1.6514    0.7307 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7933    2.2403    1.4877 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8338    0.4650    1.3722 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9330   -0.6544    0.3521 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6696   -1.7453    0.8333 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4272   -1.0338   -0.1867 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3293   -1.6434    0.8123 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4714   -0.6758    0.9373 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3725    0.2327   -0.2949 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0259    0.1232   -0.7570 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5170   -0.7116   -1.7351 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6619    1.9713   -1.2946 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8065    0.8996   -2.5265 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7144    2.1737   -1.1587 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9975    2.4644    0.6188 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9652    3.1300    1.0695 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3350    0.1339    2.3025 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8889    0.6920    1.6697 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2232   -1.7667   -1.0220 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8504   -1.8747    1.7852 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7457   -2.5902    0.4110 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4110   -0.1165    1.8715 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4604   -1.2117    0.9375 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0514   -0.1736   -1.0726 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7025    1.2459   -0.0446 H   0  0  0  0  0  0  0  0  0  0  0  0
  8  7  1  0
  7  9  1  0
  9 10  1  0
 10 11  1  1
 11  2  1  0
  2  1  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6 16  1  0
 16 15  1  0
 15 14  1  0
 14 13  1  0
 13 12  1  0
  6  7  1  0
 12 16  1  0
  4 10  1  0
 12 10  1  0
  8 22  1  0
  7 21  1  6
  9 23  1  0
  9 24  1  0
  3 17  1  0
  5 18  1  0
  5 19  1  0
  6 20  1  6
 15 30  1  0
 15 31  1  0
 14 28  1  0
 14 29  1  0
 13 26  1  0
 13 27  1  0
 12 25  1  6
M  END


  Mrv1652309082221122D          

 16 19  0  0  1  0            999 V2000
   -1.0404   -0.5717    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2991   -0.2096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1207    0.6122    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7420    0.6989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1595    1.5338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1057    1.5791    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5496    1.0776    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7559    1.3026    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7595    0.3603    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1740   -0.1075    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4635   -0.5763    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1414   -0.0514    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.7456   -0.6131    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4666   -0.2121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3080    0.5975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4890    0.6969    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  6  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
  4 10  1  0  0  0  0
 10 11  1  6  0  0  0
  2 11  1  0  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
  6 16  1  1  0  0  0
 12 16  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0272547

> <DATABASE_NAME>
NP-MRD

> <SMILES>
O[C@H]1C[C@]23OC(=O)C=C2C[C@H]1N1CCC[C@H]31

> <INCHI_IDENTIFIER>
InChI=1S/C12H15NO3/c14-9-6-12-7(5-11(15)16-12)4-8(9)13-3-1-2-10(12)13/h5,8-10,14H,1-4,6H2/t8-,9+,10-,12+/m1/s1

> <INCHI_KEY>
LXHGRIAYJAHNHR-KLBPJQLPSA-N

> <FORMULA>
C12H15NO3

> <MOLECULAR_WEIGHT>
221.256

> <EXACT_MASS>
221.105193347

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
31

> <JCHEM_AVERAGE_POLARIZABILITY>
22.32907866557654

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,2R,7R,14S)-14-hydroxy-12-oxa-6-azatetracyclo[5.5.2.0^{1,9}.0^{2,6}]tetradec-9-en-11-one

> <JCHEM_LOGP>
0.0920557436666671

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
15.09878771250236

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.15418053421029

> <JCHEM_PKA_STRONGEST_BASIC>
9.456824612855469

> <JCHEM_POLAR_SURFACE_AREA>
49.77

> <JCHEM_REFRACTIVITY>
57.117000000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2R,7R,14S)-14-hydroxy-12-oxa-6-azatetracyclo[5.5.2.0^{1,9}.0^{2,6}]tetradec-9-en-11-one

> <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  O   UNK     0      -1.942  -1.067   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      -0.558  -0.391   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.225   1.143   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.385   1.305   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.164   2.863   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.931   2.948   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.893   2.012   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       1.411   2.431   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       3.284   0.673   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.192  -0.201   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       0.865  -1.076   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       3.997  -0.096   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.125  -1.145   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.471  -0.396   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.175   1.115   0.000  0.00  0.00           C+0
HETATM   16  N   UNK     0       4.646   1.301   0.000  0.00  0.00           N+0
CONECT    1    2                                                            
CONECT    2    1    3   11                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   10                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7   16                                                  
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9    4   11   12                                             
CONECT   11   10    2                                                       
CONECT   12   10   13   16                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15    6   12                                                  
MASTER        0    0    0    0    0    0    0    0   16    0   38    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₂H₁₅NO₃

Average Mass

221.2560 Da

Monoisotopic Mass

221.10519 Da

IUPAC Name

(1S,2R,7R,14S)-14-hydroxy-12-oxa-6-azatetracyclo[5.5.2.0^{1,9}.0^{2,6}]tetradec-9-en-11-one

Traditional Name

(1S,2R,7R,14S)-14-hydroxy-12-oxa-6-azatetracyclo[5.5.2.0^{1,9}.0^{2,6}]tetradec-9-en-11-one

CAS Registry Number

Not Available

SMILES

O[C@H]1C[C@]23OC(=O)C=C2C[C@H]1N1CCC[C@H]31

InChI Identifier

InChI=1S/C12H15NO3/c14-9-6-12-7(5-11(15)16-12)4-8(9)13-3-1-2-10(12)13/h5,8-10,14H,1-4,6H2/t8-,9+,10-,12+/m1/s1

InChI Key

LXHGRIAYJAHNHR-KLBPJQLPSA-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
Phyllanthus niruri	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as azaspirodecane derivatives. These are organic compounds containing a spirodecane moiety with at least one nitrogen atom.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Azaspirodecane derivatives

Sub Class

Not Available

Direct Parent

Azaspirodecane derivatives

Alternative Parents

Substituents

Azaspirodecane
Indolizidine
Piperidine
2-furanone
N-alkylpyrrolidine
Pyrrolidine
Cyclic alcohol
Dihydrofuran
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Tertiary aliphatic amine
Tertiary amine
Secondary alcohol
Carboxylic acid ester
Amino acid or derivatives
1,2-aminoalcohol
Lactone
Carboxylic acid derivative
Oxacycle
Azacycle
Monocarboxylic acid or derivatives
Alcohol
Hydrocarbon derivative
Organic nitrogen compound
Carbonyl group
Organic oxide
Organopnictogen compound
Organic oxygen compound
Organooxygen compound
Organonitrogen compound
Amine
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic 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	0.092	ChemAxon
pKa (Strongest Acidic)	14.15	ChemAxon
pKa (Strongest Basic)	9.46	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	49.77 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	57.12 m³·mol⁻¹	ChemAxon
Polarizability	22.33 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

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

135034108

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1s,2r,7r,14s)-14-hydroxy-12-oxa-6-azatetracyclo[5.5.2.0¹,⁹.0²,⁶]tetradec-9-en-11-one (NP0272547)

MOL for NP0272547 ((1s,2r,7r,14s)-14-hydroxy-12-oxa-6-azatetracyclo[5.5.2.0¹,⁹.0²,⁶]tetradec-9-en-11-one)

3D MOL for NP0272547 ((1s,2r,7r,14s)-14-hydroxy-12-oxa-6-azatetracyclo[5.5.2.0¹,⁹.0²,⁶]tetradec-9-en-11-one)

3D SDF for NP0272547 ((1s,2r,7r,14s)-14-hydroxy-12-oxa-6-azatetracyclo[5.5.2.0¹,⁹.0²,⁶]tetradec-9-en-11-one)

3D-SDF for NP0272547 ((1s,2r,7r,14s)-14-hydroxy-12-oxa-6-azatetracyclo[5.5.2.0¹,⁹.0²,⁶]tetradec-9-en-11-one)

PDB for NP0272547 ((1s,2r,7r,14s)-14-hydroxy-12-oxa-6-azatetracyclo[5.5.2.0¹,⁹.0²,⁶]tetradec-9-en-11-one)

3D PDB for NP0272547 ((1s,2r,7r,14s)-14-hydroxy-12-oxa-6-azatetracyclo[5.5.2.0¹,⁹.0²,⁶]tetradec-9-en-11-one)

SMILES for NP0272547 ((1s,2r,7r,14s)-14-hydroxy-12-oxa-6-azatetracyclo[5.5.2.0¹,⁹.0²,⁶]tetradec-9-en-11-one)

INCHI for NP0272547 ((1s,2r,7r,14s)-14-hydroxy-12-oxa-6-azatetracyclo[5.5.2.0¹,⁹.0²,⁶]tetradec-9-en-11-one)

Structure for NP0272547 ((1s,2r,7r,14s)-14-hydroxy-12-oxa-6-azatetracyclo[5.5.2.0¹,⁹.0²,⁶]tetradec-9-en-11-one)

3D Structure for NP0272547 ((1s,2r,7r,14s)-14-hydroxy-12-oxa-6-azatetracyclo[5.5.2.0¹,⁹.0²,⁶]tetradec-9-en-11-one)