NP-MRD: Showing NP-Card for (-)-9alpha-Hydroxysophoramine (NP0066006)

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Record Information

Version

2.0

Created at

2022-04-28 10:10:13 UTC

Updated at

2022-04-28 10:10:13 UTC

NP-MRD ID

NP0066006

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(-)-9alpha-Hydroxysophoramine

Description

(1S,9S,15S,17S)-15-hydroxy-7,13-diazatetracyclo[7.7.1.0²,⁷.0¹³,¹⁷]Heptadeca-2,4-dien-6-one belongs to the class of organic compounds known as naphthyridines. Naphthyridines are compounds containing a naphthyridine moiety, a naphthalene in which a carbon atom has been replaced by a nitrogen in each of the two rings. The naphthyridine skeleton can also be described as an assembly two fused pyridine rings, which do not share their nitrogen atom. (-)-9alpha-Hydroxysophoramine is found in Sophora flavescens . Based on a literature review very few articles have been published on (1S,9S,15S,17S)-15-hydroxy-7,13-diazatetracyclo[7.7.1.0²,⁷.0¹³,¹⁷]Heptadeca-2,4-dien-6-one.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 39 42  0  0  0  0  0  0  0  0999 V2000
    3.3412   -2.0317   -1.5925 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1968   -1.0482   -0.8309 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3073   -0.4200   -0.2954 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1380    0.6575    0.5386 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8528    1.0661    0.8052 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7462    0.4241    0.2592 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9499   -0.6278   -0.5534 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7890   -1.2746   -1.1051 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1772   -1.5368    0.0605 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.2428   -2.4684   -0.3314 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6417   -2.0964   -0.0422 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8253   -0.8365    0.7537 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9188    0.1246    0.1554 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2190    1.4864    0.5342 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4223    2.3660   -0.4105 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.5724    3.6790   -0.0278 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0004    1.9055   -0.4897 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3568    0.8741    0.5536 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6044   -0.2446    0.6681 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.3117   -0.7546   -0.5158 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9757    1.1765    0.9777 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6556    1.9038    1.4510 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3139   -0.7516   -1.9319 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0823   -2.2911   -1.4937 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4787   -2.0515    0.8270 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0751   -3.5035    0.0951 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1662   -2.6490   -1.4462 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2595   -1.9624   -0.9792 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2033   -2.9009    0.5189 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4848   -1.0577    1.8021 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8603   -0.5192    0.7582 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2844    1.7286    0.4558 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8017    1.6393    1.5475 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8671    2.2753   -1.4373 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4754    4.2896   -0.8016 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6387    2.8098   -0.2575 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3029    1.6100   -1.5154 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4366    1.4462    1.5256 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7727   -0.4360    1.7701 H   0  0  0  0  0  0  0  0  0  0  0  0
 16 15  1  0
 15 17  1  0
 17 18  1  0
 18 19  1  0
 19  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
  9  8  1  0
  8  7  1  0
  7  2  1  0
  2  1  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
 14 15  1  0
  6  7  1  0
  6 18  1  0
 13 19  1  0
 16 35  1  0
 15 34  1  6
 17 36  1  0
 17 37  1  0
 18 38  1  1
 19 39  1  1
  9 25  1  1
 10 26  1  0
 10 27  1  0
 11 28  1  0
 11 29  1  0
 12 30  1  0
 12 31  1  0
 14 32  1  0
 14 33  1  0
  8 23  1  0
  8 24  1  0
  3 20  1  0
  4 21  1  0
  5 22  1  0
M  END


  Mrv1652304282212102D          

 19 22  0  0  1  0            999 V2000
    0.0000    0.0000    0.0000 C   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
   -0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -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  1  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  2  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
    2.1434   -0.4125    0.0000 N   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 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -3.7125    0.0000 O   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
    3.5724   -1.2375    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
    2.8579   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  5  4  1  1  0  0  0
  5  6  1  0  0  0  0
  6  1  1  1  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
 10  9  1  1  0  0  0
  5 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
  4 13  1  0  0  0  0
 12 14  1  6  0  0  0
  9 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
  8 18  1  0  0  0  0
 18 19  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0066006

> <DATABASE_NAME>
NP-MRD

> <SMILES>
O[C@H]1C[C@H]2[C@@H]3[C@@H](CCCN3C1)CN1C(=O)C=CC=C21

> <INCHI_IDENTIFIER>
InChI=1S/C15H20N2O2/c18-11-7-12-13-4-1-5-14(19)17(13)8-10-3-2-6-16(9-11)15(10)12/h1,4-5,10-12,15,18H,2-3,6-9H2/t10-,11-,12+,15-/m0/s1

> <INCHI_KEY>
ZOODLPNNEYPMNC-OHTBPHCPSA-N

> <FORMULA>
C15H20N2O2

> <MOLECULAR_WEIGHT>
260.337

> <EXACT_MASS>
260.152477892

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
39

> <JCHEM_AVERAGE_POLARIZABILITY>
28.136368674099163

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,9S,15S,17S)-15-hydroxy-7,13-diazatetracyclo[7.7.1.0^{2,7}.0^{13,17}]heptadeca-2,4-dien-6-one

> <ALOGPS_LOGP>
1.33

> <JCHEM_LOGP>
-0.06157607500000076

> <ALOGPS_LOGS>
-1.04

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.862938470647183

> <JCHEM_PKA_STRONGEST_BASIC>
8.770958718812674

> <JCHEM_POLAR_SURFACE_AREA>
43.78

> <JCHEM_REFRACTIVITY>
75.39669999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.36e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,9S,15S,17S)-15-hydroxy-7,13-diazatetracyclo[7.7.1.0^{2,7}.0^{13,17}]heptadeca-2,4-dien-6-one

> <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  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    4  N   UNK     0       0.000  -3.080   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    8  N   UNK     0       4.001  -0.770   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       1.334  -6.930   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.335  -0.000   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       5.335   1.540   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5   13                                                  
CONECT    5    4    6   10                                                  
CONECT    6    5    1    7                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   18                                                  
CONECT    9    8   10   15                                                  
CONECT   10    9    5   11                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12    4                                                       
CONECT   14   12                                                            
CONECT   15    9   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17    8   19                                                  
CONECT   19   18                                                            
MASTER        0    0    0    0    0    0    0    0   19    0   44    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₅H₂₀N₂O₂

Average Mass

260.3370 Da

Monoisotopic Mass

260.15248 Da

IUPAC Name

(1S,9S,15S,17S)-15-hydroxy-7,13-diazatetracyclo[7.7.1.0^{2,7}.0^{13,17}]heptadeca-2,4-dien-6-one

Traditional Name

(1S,9S,15S,17S)-15-hydroxy-7,13-diazatetracyclo[7.7.1.0^{2,7}.0^{13,17}]heptadeca-2,4-dien-6-one

CAS Registry Number

Not Available

SMILES

O[C@H]1C[C@H]2[C@@H]3[C@@H](CCCN3C1)CN1C(=O)C=CC=C21

InChI Identifier

InChI=1S/C15H20N2O2/c18-11-7-12-13-4-1-5-14(19)17(13)8-10-3-2-6-16(9-11)15(10)12/h1,4-5,10-12,15,18H,2-3,6-9H2/t10-,11-,12+,15-/m0/s1

InChI Key

ZOODLPNNEYPMNC-OHTBPHCPSA-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
Sophora flavescens	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as naphthyridines. Naphthyridines are compounds containing a naphthyridine moiety, a naphthalene in which a carbon atom has been replaced by a nitrogen in each of the two rings. The naphthyridine skeleton can also be described as an assembly two fused pyridine rings, which do not share their nitrogen atom.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Diazanaphthalenes

Sub Class

Naphthyridines

Direct Parent

Naphthyridines

Alternative Parents

Substituents

Naphthyridine
Quinolizidine
Pyridinone
Aralkylamine
Piperidine
Pyridine
Heteroaromatic compound
Lactam
1,2-aminoalcohol
Secondary alcohol
Tertiary amine
Tertiary aliphatic amine
Azacycle
Organic nitrogen compound
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Organic oxide
Alcohol
Amine
Organopnictogen compound
Organic oxygen compound
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	1.33	ALOGPS
logP	-0.062	ChemAxon
logS	-1	ALOGPS
pKa (Strongest Acidic)	14.86	ChemAxon
pKa (Strongest Basic)	8.77	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	43.78 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	75.4 m³·mol⁻¹	ChemAxon
Polarizability	28.14 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

154495910

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for (-)-9alpha-Hydroxysophoramine (NP0066006)

MOL for NP0066006 ((-)-9alpha-Hydroxysophoramine)

3D MOL for NP0066006 ((-)-9alpha-Hydroxysophoramine)

3D SDF for NP0066006 ((-)-9alpha-Hydroxysophoramine)

3D-SDF for NP0066006 ((-)-9alpha-Hydroxysophoramine)

PDB for NP0066006 ((-)-9alpha-Hydroxysophoramine)

3D PDB for NP0066006 ((-)-9alpha-Hydroxysophoramine)

SMILES for NP0066006 ((-)-9alpha-Hydroxysophoramine)

INCHI for NP0066006 ((-)-9alpha-Hydroxysophoramine)

Structure for NP0066006 ((-)-9alpha-Hydroxysophoramine)

3D Structure for NP0066006 ((-)-9alpha-Hydroxysophoramine)