NP-MRD: Showing NP-Card for 5alpha-Hydroxysophocarpine (NP0055162)

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Record Information

Version

2.0

Created at

2022-04-28 01:17:49 UTC

Updated at

2022-04-28 01:17:49 UTC

NP-MRD ID

NP0055162

Secondary Accession Numbers

None

Natural Product Identification

Common Name

5alpha-Hydroxysophocarpine

Description

5Alpha-Hydroxysophocarpine belongs to the class of organic compounds known as matrine alkaloids. These are lupin alkaloids with a structure based on the matrine skeleton, a four-ring skeleton that based on a saturated dipyrido[2,1-f:3',2',1'-Ij][1,6]naphthyridin-10-one skeleton. 5alpha-Hydroxysophocarpine is found in Sophora flavescens, Sophora flavescens var. angustifolia and Sophora tonkinensis. 5alpha-Hydroxysophocarpine was first documented in 2015 (PMID: 26132528). Based on a literature review very few articles have been published on 5alpha-Hydroxysophocarpine.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 41 44  0  0  0  0  0  0  0  0999 V2000
    3.3423   -2.4639    0.1449 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0019   -1.2529   -0.1143 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0677   -0.2847   -0.2441 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7251    0.9625   -0.5108 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3543    1.4460   -0.6862 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2656    0.4801   -0.4399 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4069    0.8204    0.7639 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0185    2.2515    0.8175 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6608    2.5895   -0.5116 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8839    1.7144   -0.6374 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6164    0.3153   -0.5320 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9162   -0.3507   -0.3403 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7615   -1.8270   -0.3946 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6869   -2.3708    0.4988 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5297   -1.4706    0.7087 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0263   -1.7230    2.0068 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5846   -1.8826   -0.2421 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6450   -0.8954   -0.2635 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8456   -0.0143    0.6447 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.1185   -0.5017   -0.1402 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5105    1.7194   -0.6147 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2946    1.8698   -1.7353 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2403    2.3480   -0.0417 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6019    0.4774   -1.3628 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9421    0.5220    1.6609 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8637    2.2959    1.5679 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7223    2.9668    1.1588 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0139    2.5139   -1.3628 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0174    3.6429   -0.4606 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3781    1.9543   -1.5781 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5740    1.9969    0.1829 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3016    0.0202    0.6357 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6391   -0.0381   -1.1039 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6072   -2.1143   -1.4661 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7360   -2.2865   -0.1110 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3360   -3.3327    0.0232 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1657   -2.6873    1.4585 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0103   -2.7033    2.1842 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0080   -2.8228    0.1688 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2072   -2.1178   -1.2546 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4779    0.2334    1.5226 H   0  0  0  0  0  0  0  0  0  0  0  0
 15 16  1  1
 15 14  1  0
 14 13  1  0
 13 12  1  0
 12 11  1  0
 11 10  1  0
 10  9  1  0
  9  8  1  0
  8  7  1  0
  7  6  1  0
  6  5  1  0
  5  4  1  0
  4  3  2  0
  3  2  1  0
  2  1  2  0
  2 18  1  0
 18 17  1  0
  7 19  1  0
 17 15  1  0
 19 15  1  0
 19 11  1  0
 18  6  1  0
 16 38  1  0
 14 36  1  0
 14 37  1  0
 13 34  1  0
 13 35  1  0
 12 32  1  0
 12 33  1  0
 10 30  1  0
 10 31  1  0
  9 28  1  0
  9 29  1  0
  8 26  1  0
  8 27  1  0
  7 25  1  1
  6 24  1  6
  5 22  1  0
  5 23  1  0
  4 21  1  0
  3 20  1  0
 17 39  1  0
 17 40  1  0
 19 41  1  1
M  END


  Mrv1652304282203172D          

 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  1  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  0  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
    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
    0.7145    0.4125    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
  1  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  9  8  1  6  0  0  0
  9 10  1  0  0  0  0
  5 10  1  0  0  0  0
 10 11  1  1  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
  4 13  1  0  0  0  0
  9 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
  8 17  1  0  0  0  0
 17 18  2  0  0  0  0
  6 19  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0055162

> <DATABASE_NAME>
NP-MRD

> <SMILES>
O[C@]12CCCN3CCC[C@H]([C@H]4CC=CC(=O)N4C1)[C@H]23

> <INCHI_IDENTIFIER>
InChI=1S/C15H22N2O2/c18-13-6-1-5-12-11-4-2-8-16-9-3-7-15(19,14(11)16)10-17(12)13/h1,6,11-12,14,19H,2-5,7-10H2/t11-,12-,14-,15-/m1/s1

> <INCHI_KEY>
RWGCPRXNEWRKMS-QHSBEEBCSA-N

> <FORMULA>
C15H22N2O2

> <MOLECULAR_WEIGHT>
262.353

> <EXACT_MASS>
262.168127956

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
41

> <JCHEM_AVERAGE_POLARIZABILITY>
28.753035198059226

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,2R,9R,17R)-9-hydroxy-7,13-diazatetracyclo[7.7.1.0^{2,7}.0^{13,17}]heptadec-4-en-6-one

> <ALOGPS_LOGP>
0.88

> <JCHEM_LOGP>
0.2626629596666661

> <ALOGPS_LOGS>
-1.15

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
18.535711543018454

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.798549584941483

> <JCHEM_PKA_STRONGEST_BASIC>
9.398420866661718

> <JCHEM_POLAR_SURFACE_AREA>
43.78

> <JCHEM_REFRACTIVITY>
73.7837

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.87e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2R,9R,17R)-9-hydroxy-7,13-diazatetracyclo[7.7.1.0^{2,7}.0^{13,17}]heptadec-4-en-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  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.335  -0.000   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       5.335   1.540   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       1.334   0.770   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   19                                             
CONECT    7    6    8                                                       
CONECT    8    7    9   17                                                  
CONECT    9    8   10   14                                                  
CONECT   10    9    5   11                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12    4                                                       
CONECT   14    9   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16    8   18                                                  
CONECT   18   17                                                            
CONECT   19    6                                                            
MASTER        0    0    0    0    0    0    0    0   19    0   44    0
END

View in JSmol

Synonyms

Value	Source
5a-Hydroxysophocarpine	Generator
5Α-hydroxysophocarpine	Generator

Chemical Formula

C₁₅H₂₂N₂O₂

Average Mass

262.3530 Da

Monoisotopic Mass

262.16813 Da

IUPAC Name

(1R,2R,9R,17R)-9-hydroxy-7,13-diazatetracyclo[7.7.1.0^{2,7}.0^{13,17}]heptadec-4-en-6-one

Traditional Name

(1R,2R,9R,17R)-9-hydroxy-7,13-diazatetracyclo[7.7.1.0^{2,7}.0^{13,17}]heptadec-4-en-6-one

CAS Registry Number

Not Available

SMILES

O[C@]12CCCN3CCC[C@H]([C@H]4CC=CC(=O)N4C1)[C@H]23

InChI Identifier

InChI=1S/C15H22N2O2/c18-13-6-1-5-12-11-4-2-8-16-9-3-7-15(19,14(11)16)10-17(12)13/h1,6,11-12,14,19H,2-5,7-10H2/t11-,12-,14-,15-/m1/s1

InChI Key

RWGCPRXNEWRKMS-QHSBEEBCSA-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	LOTUS Database	35616633
Sophora flavescens var. angustifolia	Plant	KNApSAcK
Sophora tonkinensis	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as matrine alkaloids. These are lupin alkaloids with a structure based on the matrine skeleton, a four-ring skeleton that based on a saturated dipyrido[2,1-f:3',2',1'-Ij][1,6]naphthyridin-10-one skeleton.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Lupin alkaloids

Sub Class

Matrine alkaloids

Direct Parent

Matrine alkaloids

Alternative Parents

Substituents

Matrine
Diazanaphthalene
Naphthyridine
Quinolizidine
Piperidine
Tertiary alcohol
Tertiary carboxylic acid amide
1,2-aminoalcohol
Amino acid or derivatives
Carboxamide group
Lactam
Tertiary amine
Tertiary aliphatic amine
Carboxylic acid derivative
Azacycle
Organoheterocyclic compound
Organopnictogen compound
Organooxygen compound
Organonitrogen compound
Organic oxygen compound
Organic nitrogen compound
Amine
Organic oxide
Hydrocarbon derivative
Alcohol
Carbonyl group
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	0.88	ALOGPS
logP	0.26	ChemAxon
logS	-1.2	ALOGPS
pKa (Strongest Acidic)	13.8	ChemAxon
pKa (Strongest Basic)	9.4	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	73.78 m³·mol⁻¹	ChemAxon
Polarizability	28.75 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

C00007762

Chemspider ID

59004336

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

15385686

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Pan QM, Li YH, Hua J, Huang FP, Wang HS, Liang D: Antiviral Matrine-Type Alkaloids from the Rhizomes of Sophora tonkinensis. J Nat Prod. 2015 Jul 24;78(7):1683-8. doi: 10.1021/acs.jnatprod.5b00325. Epub 2015 Jul 1. [PubMed:26132528 ]

Showing NP-Card for 5alpha-Hydroxysophocarpine (NP0055162)

MOL for NP0055162 (5alpha-Hydroxysophocarpine)

3D MOL for NP0055162 (5alpha-Hydroxysophocarpine)

3D SDF for NP0055162 (5alpha-Hydroxysophocarpine)

3D-SDF for NP0055162 (5alpha-Hydroxysophocarpine)

PDB for NP0055162 (5alpha-Hydroxysophocarpine)

3D PDB for NP0055162 (5alpha-Hydroxysophocarpine)

SMILES for NP0055162 (5alpha-Hydroxysophocarpine)

INCHI for NP0055162 (5alpha-Hydroxysophocarpine)

Structure for NP0055162 (5alpha-Hydroxysophocarpine)

3D Structure for NP0055162 (5alpha-Hydroxysophocarpine)