NP-MRD: Showing NP-Card for (−)-2-Oxy-10α-hydroxysophoridine (NP0331672)

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Record Information

Version

2.0

Created at

2023-06-04 16:00:17 UTC

Updated at

2024-09-03 04:16:27 UTC

NP-MRD ID

NP0331672

Natural Product DOI

https://doi.org/10.57994/0668

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(−)-2-Oxy-10α-hydroxysophoridine

Description

(−)-2-Oxy-10α-hydroxysophoridine 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. (−)-2-Oxy-10α-hydroxysophoridine was first documented in 2021 (PMID: 34521046). Based on a literature review very few articles have been published on (−)-2-Oxy-10α-hydroxysophoridine.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652306042318002D          

 24 27  0  0  1  0            999 V2000
    3.5724    2.0625    0.0000 O   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
    4.2868    0.8250    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
    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  1  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    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
    2.1434    0.4125    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8579   -0.8250    0.0000 H   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  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  2  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 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    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
    1.4289    0.8250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7145    0.4125    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4289   -0.8250    0.0000 H   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  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  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
  2  7  1  0  0  0  0
  7  8  1  0  0  0  0
  6  9  1  1  0  0  0
  6 10  1  0  0  0  0
 10 11  1  6  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  6  0  0  0
 14 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
 19 20  1  0  0  0  0
  8 20  1  0  0  0  0
 20 21  1  1  0  0  0
 20 22  1  0  0  0  0
 16 22  1  0  0  0  0
 10 22  1  0  0  0  0
 22 23  1  6  0  0  0
 17 24  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0331672

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@@]12CCC(=O)N3[C@@H](O)CC[C@]([H])([C@@]4([H])CCCC(=O)N4C1)[C@]23[H]

> <INCHI_IDENTIFIER>
InChI=1S/C15H22N2O3/c18-12-3-1-2-11-10-5-7-14(20)17-13(19)6-4-9(15(10)17)8-16(11)12/h9-11,14-15,20H,1-8H2/t9-,10-,11-,14+,15+/m1/s1

> <INCHI_KEY>
YYDDHJWOEVSCAO-UPYBOPHASA-N

> <FORMULA>
C15H22N2O3

> <MOLECULAR_WEIGHT>
278.352

> <EXACT_MASS>
278.163042576

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
42

> <JCHEM_AVERAGE_POLARIZABILITY>
29.689094860520136

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,2R,9R,14S,17S)-14-hydroxy-7,13-diazatetracyclo[7.7.1.0^{2,7}.0^{13,17}]heptadecane-6,12-dione

> <JCHEM_LOGP>
-0.4688982606666672

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.497931425425946

> <JCHEM_PKA_STRONGEST_BASIC>
-0.30212129867412674

> <JCHEM_POLAR_SURFACE_AREA>
60.85000000000001

> <JCHEM_REFRACTIVITY>
72.2143

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2R,9R,14S,17S)-14-hydroxy-7,13-diazatetracyclo[7.7.1.0^{2,7}.0^{13,17}]heptadecane-6,12-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-JUN-23   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-JUN-23         0                                  
HETATM    1  O   UNK     0       6.668   3.850   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.002  -0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.335  -0.000   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0       5.335   1.540   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM    9  H   UNK     0       4.001   0.770   0.000  0.00  0.00           H+0
HETATM   10  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   11  H   UNK     0       5.335  -1.540   0.000  0.00  0.00           H+0
HETATM   12  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       0.000  -3.080   0.000  0.00  0.00           O+0
HETATM   16  N   UNK     0       1.334  -0.770   0.000  0.00  0.00           N+0
HETATM   17  C   UNK     0      -0.000   0.000   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   21  H   UNK     0       1.334   0.770   0.000  0.00  0.00           H+0
HETATM   22  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   23  H   UNK     0       2.667  -1.540   0.000  0.00  0.00           H+0
HETATM   24  O   UNK     0      -1.334  -0.770   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    7                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    9   10                                             
CONECT    7    6    2    8                                                  
CONECT    8    7   20                                                       
CONECT    9    6                                                            
CONECT   10    6   11   12   22                                             
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17   22                                                  
CONECT   17   16   18   24                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19    8   21   22                                             
CONECT   21   20                                                            
CONECT   22   20   16   10   23                                             
CONECT   23   22                                                            
CONECT   24   17                                                            
MASTER        0    0    0    0    0    0    0    0   24    0   54    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₅H₂₂N₂O₃

Average Mass

278.3520 Da

Monoisotopic Mass

278.16304 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

[H][C@@]12CCC(=O)N3[C@@H](O)CC[C@]([H])([C@@]4([H])CCCC(=O)N4C1)[C@]23[H]

InChI Identifier

InChI=1S/C15H22N2O3/c18-12-3-1-2-11-10-5-7-14(20)17-13(19)6-4-9(15(10)17)8-16(11)12/h9-11,14-15,20H,1-8H2/t9-,10-,11-,14+,15+/m1/s1

InChI Key

YYDDHJWOEVSCAO-UPYBOPHASA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D_DEPT NMR	¹³C NMR Spectrum (1D, 101 MHz, CDCl3, experimental)	luoding225@hotmail.com	Not Available	Not Available	2024-05-11	View Spectrum
NOESY NMR	[¹H, ¹H] NMR Spectrum (2D, 400 MHz, CDCl3, experimental)	luoding225@hotmail.com	Not Available	Not Available	2023-06-04	View Spectrum
HMBC NMR	[¹H, ¹³C] NMR Spectrum (2D, 400 MHz, CDCl3, experimental)	luoding225@hotmail.com	Not Available	Not Available	2023-06-04	View Spectrum
COSY NMR	[¹H, ¹H] NMR Spectrum (2D, 400 MHz, CDCl3, experimental)	luoding225@hotmail.com	Not Available	Not Available	2023-06-04	View Spectrum
HSQC NMR	[¹H, ¹³C] NMR Spectrum (2D, 400 MHz, CDCl3, experimental)	luoding225@hotmail.com	Not Available	Not Available	2023-06-04	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, CDCl3, experimental)	luoding225@hotmail.com	Not Available	Not Available	2023-06-04	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CDCl3, experimental)	luoding225@hotmail.com	Not Available	Not Available	2023-06-04	View Spectrum

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View

Chemical Shift Submissions

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 100.620817547, CDCl₃, simulated)	luoding225@hotmail.com	Jinan University	Ding Luo	2024-05-11	View Spectrum

Species

Species of Origin

Species Name	Source	Reference
alopecuroides		Not Available

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
Quinolizidinone
Diazanaphthalene
Quinolizidine
Naphthyridine
N-acyl-piperidine
Piperidinone
Delta-lactam
Piperidine
N-acyl-amine
Tertiary carboxylic acid amide
Lactam
Carboxamide group
Azacycle
Organoheterocyclic compound
Carboxylic acid derivative
Alkanolamine
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
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

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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for (−)-2-Oxy-10α-hydroxysophoridine (NP0331672)

MOL for NP0331672 ((−)-2-Oxy-10α-hydroxysophoridine)

3D MOL for NP0331672 ((−)-2-Oxy-10α-hydroxysophoridine)

3D SDF for NP0331672 ((−)-2-Oxy-10α-hydroxysophoridine)

3D-SDF for NP0331672 ((−)-2-Oxy-10α-hydroxysophoridine)

PDB for NP0331672 ((−)-2-Oxy-10α-hydroxysophoridine)

3D PDB for NP0331672 ((−)-2-Oxy-10α-hydroxysophoridine)

SMILES for NP0331672 ((−)-2-Oxy-10α-hydroxysophoridine)

INCHI for NP0331672 ((−)-2-Oxy-10α-hydroxysophoridine)

Structure for NP0331672 ((−)-2-Oxy-10α-hydroxysophoridine)

3D Structure for NP0331672 ((−)-2-Oxy-10α-hydroxysophoridine)