NP-MRD: Showing NP-Card for α-erythroidine (NP0143724)

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Record Information

Version

2.0

Created at

2022-09-01 22:33:24 UTC

Updated at

2022-09-01 22:33:24 UTC

NP-MRD ID

NP0143724

Secondary Accession Numbers

None

Natural Product Identification

Common Name

α-erythroidine

Description

Alpha-Erythroidine, also known as α-erythroidine, belongs to the class of organic compounds known as erythrinanes. These are erythrina alkaloids possessing either a 6-5-6-6-membered indoloisoquinoline core or a derivative thereof. α-erythroidine is found in Erythrina americana and Erythrina berteroana. α-erythroidine was first documented in 2014 (PMID: 25116117). Based on a literature review very few articles have been published on alpha-Erythroidine.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 39 42  0  0  0  0  0  0  0  0999 V2000
    3.4395    1.7203    2.1600 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2091    0.5076    1.5185 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1858    0.6047    0.5699 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.7762    0.3425   -0.7442 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2006   -0.5811   -1.5246 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0203   -1.3255   -1.1155 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5215   -2.4985   -1.4556 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7337   -2.8040   -0.7224 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6705   -1.8199    0.3335 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0433   -1.3927    0.4957 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2463   -0.1217    1.2263 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7238    0.9859    0.3061 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.9258    1.4969   -0.4482 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4644    2.3784   -1.4724 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5443    1.8007   -2.3702 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5008    2.1989   -3.5581 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6781    0.7453   -1.8380 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7341    0.3389   -0.5936 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1417   -0.7103   -0.1038 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0696   -0.2608    0.9993 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4963    2.0095    2.6642 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7480    2.4670    1.3940 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2801    1.5905    2.8548 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8303    1.6705    0.5981 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6389    0.8893   -1.0380 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6452   -0.7648   -2.4893 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9691   -3.1840   -2.1942 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6876   -3.8453   -0.3207 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6264   -2.6681   -1.3674 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6364   -2.2425    0.9450 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4663   -1.2816   -0.5420 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3631   -0.0208    1.3722 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8204   -0.0964    2.2273 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2721    1.7673    0.9403 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5502    2.0518    0.2848 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4590    0.6386   -0.8875 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0278    0.2902   -2.4951 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4779    0.2905    1.7566 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4687   -1.1671    1.4953 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3 20  1  0
 19 20  1  1
 19  9  1  0
  9  8  1  0
  8  7  1  0
  7  6  2  0
  6  5  1  0
  5  4  2  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 15 17  1  0
 17 18  2  0
  4  3  1  0
 18 12  1  0
  6 19  1  0
 18 19  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  3 24  1  6
 20 38  1  0
 20 39  1  0
  8 28  1  0
  8 29  1  0
  7 27  1  0
  5 26  1  0
  4 25  1  0
 10 30  1  0
 10 31  1  0
 11 32  1  0
 11 33  1  0
 12 34  1  1
 13 35  1  0
 13 36  1  0
 17 37  1  0
M  END


  Mrv1652309022200332D          

 20 23  0  0  1  0            999 V2000
    3.4259   -1.5204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1564   -0.7407    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3464   -0.5842    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8059   -1.2074    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9958   -1.0509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7264   -0.2711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0334    0.0504    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0376    0.8723    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8413    1.0588    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2404    1.7808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0653    1.7961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4910    1.0894    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3158    1.1047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7415    0.3980    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3423   -0.3240    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7680   -1.0306    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5175   -0.3393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9416    0.5460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2669    0.3521    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0770    0.1956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  3  2  1  1  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  1  0  0  0  0
 10 11  1  0  0  0  0
 12 11  1  6  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  2  0  0  0  0
 15 17  1  0  0  0  0
 17 18  2  0  0  0  0
 12 18  1  0  0  0  0
 18 19  1  0  0  0  0
  6 19  1  0  0  0  0
 19  9  1  1  0  0  0
 19 20  1  0  0  0  0
  3 20  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0143724

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CO[C@@H]1C[C@]23N(CC=C2C=C1)CC[C@@H]1COC(=O)C=C31

> <INCHI_IDENTIFIER>
InChI=1S/C16H19NO3/c1-19-13-3-2-12-5-7-17-6-4-11-10-20-15(18)8-14(11)16(12,17)9-13/h2-3,5,8,11,13H,4,6-7,9-10H2,1H3/t11-,13+,16+/m1/s1

> <INCHI_KEY>
IXPDLJKEPLTCOU-FFSVYQOJSA-N

> <FORMULA>
C16H19NO3

> <MOLECULAR_WEIGHT>
273.332

> <EXACT_MASS>
273.136493476

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
39

> <JCHEM_AVERAGE_POLARIZABILITY>
28.794666799064636

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,7S,16R)-16-methoxy-5-oxa-10-azatetracyclo[8.7.0.0^{1,13}.0^{2,7}]heptadeca-2,12,14-trien-4-one

> <ALOGPS_LOGP>
1.61

> <JCHEM_LOGP>
0.808414057666666

> <ALOGPS_LOGS>
-1.95

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.85046375646873

> <JCHEM_PKA_STRONGEST_BASIC>
9.263268932245072

> <JCHEM_POLAR_SURFACE_AREA>
38.77

> <JCHEM_REFRACTIVITY>
78.12840000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.06e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,7S,16R)-16-methoxy-5-oxa-10-azatetracyclo[8.7.0.0^{1,13}.0^{2,7}]heptadeca-2,12,14-trien-4-one

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 02-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-SEP-22         0                                  
HETATM    1  C   UNK     0       6.395  -2.838   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       5.892  -1.383   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       4.380  -1.090   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.371  -2.254   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.859  -1.962   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.356  -0.506   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.062   0.094   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.070   1.628   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0       1.570   1.976   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0       2.315   3.324   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.855   3.353   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.650   2.034   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.190   2.062   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       6.984   0.743   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       6.239  -0.605   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       7.034  -1.924   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       4.699  -0.633   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.624   1.019   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.365   0.657   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       3.877   0.365   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   20                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   19                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   19                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   18                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18                                                       
CONECT   18   17   12   19                                                  
CONECT   19   18    6    9   20                                             
CONECT   20   19    3                                                       
MASTER        0    0    0    0    0    0    0    0   20    0   46    0
END

View in JSmol

Synonyms

Value	Source
a-Erythroidine	Generator
Α-erythroidine	Generator

Chemical Formula

C₁₆H₁₉NO₃

Average Mass

273.3320 Da

Monoisotopic Mass

273.13649 Da

IUPAC Name

(1S,7S,16R)-16-methoxy-5-oxa-10-azatetracyclo[8.7.0.0^{1,13}.0^{2,7}]heptadeca-2,12,14-trien-4-one

Traditional Name

(1S,7S,16R)-16-methoxy-5-oxa-10-azatetracyclo[8.7.0.0^{1,13}.0^{2,7}]heptadeca-2,12,14-trien-4-one

CAS Registry Number

Not Available

SMILES

CO[C@@H]1C[C@]23N(CC=C2C=C1)CC[C@@H]1COC(=O)C=C31

InChI Identifier

InChI=1S/C16H19NO3/c1-19-13-3-2-12-5-7-17-6-4-11-10-20-15(18)8-14(11)16(12,17)9-13/h2-3,5,8,11,13H,4,6-7,9-10H2,1H3/t11-,13+,16+/m1/s1

InChI Key

IXPDLJKEPLTCOU-FFSVYQOJSA-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
Erythrina americana	LOTUS Database	35616633
Erythrina berteroana	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as erythrinanes. These are erythrina alkaloids possessing either a 6-5-6-6-membered indoloisoquinoline core or a derivative thereof.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Erythrina alkaloids

Sub Class

Erythrinanes

Direct Parent

Erythrinanes

Alternative Parents

Substituents

Lactonic erythrinane skeleton
Azaspirodecane
Indole or derivatives
Dihydropyranone
Piperidine
Pyran
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Pyrroline
Amino acid or derivatives
Carboxylic acid ester
Lactone
Tertiary aliphatic amine
Tertiary amine
Carboxylic acid derivative
Dialkyl ether
Ether
Oxacycle
Azacycle
Monocarboxylic acid or derivatives
Organoheterocyclic compound
Hydrocarbon derivative
Organic oxide
Amine
Organic nitrogen compound
Organic oxygen compound
Carbonyl group
Organonitrogen compound
Organooxygen compound
Organopnictogen compound
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

indole alkaloid (CHEBI:27674 )
Isoquinoline alkaloids (C06531 )

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	1.61	ALOGPS
logP	0.81	ChemAxon
logS	-2	ALOGPS
pKa (Strongest Acidic)	15.85	ChemAxon
pKa (Strongest Basic)	9.26	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	38.77 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	78.13 m³·mol⁻¹	ChemAxon
Polarizability	28.79 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	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

C00001853

Chemspider ID

389882

KEGG Compound ID

C06531

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

441076

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Djiogue S, Halabalaki M, Njamen D, Kretzschmar G, Lambrinidis G, Hoepping J, Raffaelli FM, Mikros E, Skaltsounis AL, Vollmer G: Erythroidine alkaloids: a novel class of phytoestrogens. Planta Med. 2014 Jul;80(11):861-9. doi: 10.1055/s-0034-1382861. Epub 2014 Aug 12. [PubMed:25116117 ]
LOTUS database [Link]

Showing NP-Card for α-erythroidine (NP0143724)

MOL for NP0143724 (α-erythroidine)

3D MOL for NP0143724 (α-erythroidine)

3D SDF for NP0143724 (α-erythroidine)

3D-SDF for NP0143724 (α-erythroidine)

PDB for NP0143724 (α-erythroidine)

3D PDB for NP0143724 (α-erythroidine)

SMILES for NP0143724 (α-erythroidine)

INCHI for NP0143724 (α-erythroidine)

Structure for NP0143724 (α-erythroidine)

3D Structure for NP0143724 (α-erythroidine)