NP-MRD: Showing NP-Card for Baptifoline (NP0047656)

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Record Information

Version

2.0

Created at

2022-03-17 20:43:46 UTC

Updated at

2022-03-17 20:43:47 UTC

NP-MRD ID

NP0047656

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Baptifoline

Description

Baptifoline, also known as alkaloid P3?, Belongs to the class of organic compounds known as anagyrine-type alkaloids. These are lupin alkaloids with a structure based on the anagyrine skeleton. Anagyrine is a tetracyclic ketone containing a quinolizidine, and two pyridine rings fused together to form dipyrido[1,2-a:1',2'-E][1,5]diazocin-4-one. Baptifoline is a very strong basic compound (based on its pKa). Outside of the human body, baptifoline has been detected, but not quantified in, coffee and coffee products. Baptifoline is found in Ammodendron argenteum O.Ktze., Anagyris foetida, Anarthrophyllum elegans, Baptisia perfoliata, Baptisia simplicifolia, Bolusanthus speciosus, Caulophyllum thalictroides, Clathrotropis glaucophylla, Dermatophyllum secundiflorum, Dicraeopetalum stipulare, Echinosophora koreensis, Euchresta japonica, Genista lobelii, Genista lydia, Genista pilosa, Laburnum watereri, Lamprolobium fruticosum, Lamprolobium grandiflorum, Lupinus shockleyi, Maackia amurensis, Maackia tenuifolia, Petteria ramentacea, Plagiocarpus axillaris, Platycelyphium voense, Retama monosperma, Retama spp., Sophora alopecuroides, Sophora chrysophylla, Sophora flavescens, Sophora macrocarpa, Sophora tetraptera, Sophora tomentosa, Sophora tonkinensis, Spartium junceum , Thermopsis alterniflora Rgl., Thermopsis chinensis, Thermopsis licentiana, Ulex airensis, Ulex australis, Ulex densus, Ulex minor, Ulex parviflorus and Ulex jussiaei. This could make baptifoline a potential biomarker for the consumption of these foods.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 05061307082D          

 19 22  0  0  0  0            999 V2000
   -0.3627    2.4031    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3752    2.0342    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0636    2.4887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8015    2.1198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8510    1.2963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1625    0.8417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4246    1.2107    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3605    0.8417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4408    0.0397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3605    0.0397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1625   -0.0397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0824   -0.8417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3605   -1.2427    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3737   -2.0676    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3340   -2.4915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0550   -2.0905    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0683   -1.2656    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3605   -0.8417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7628   -2.5144    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
  2  7  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  6 11  1  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
  9 18  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
 13 14  1  0  0  0  0
 13 18  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 19  1  0  0  0  0
 17 18  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0047656

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC1CCN2CC3CC(CN4C(=O)C=CC=C34)C2C1

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

> <INCHI_KEY>
AOOCSKCGZYCEJX-UHFFFAOYSA-N

> <FORMULA>
C15H20N2O2

> <MOLECULAR_WEIGHT>
260.3315

> <EXACT_MASS>
260.152477894

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
27.89396993673145

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
12-hydroxy-7,15-diazatetracyclo[7.7.1.0²,⁷.0¹⁰,¹⁵]heptadeca-2,4-dien-6-one

> <ALOGPS_LOGP>
1.20

> <JCHEM_LOGP>
-0.5189790070000008

> <ALOGPS_LOGS>
-1.07

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.169454069354025

> <JCHEM_PKA_STRONGEST_BASIC>
8.670226444811446

> <JCHEM_POLAR_SURFACE_AREA>
43.78

> <JCHEM_REFRACTIVITY>
75.61749999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.24e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
12-hydroxy-7,15-diazatetracyclo[7.7.1.0²,⁷.0¹⁰,¹⁵]heptadeca-2,4-dien-6-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  O   UNK     0      -0.677   4.486   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       0.700   3.797   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.985   4.646   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.363   3.957   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.455   2.420   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.170   1.571   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0       0.793   2.260   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0      -0.673   1.571   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.823   0.074   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.673   0.074   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.170  -0.074   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.020  -1.571   0.000  0.00  0.00           C+0
HETATM   13  N   UNK     0       0.673  -2.320   0.000  0.00  0.00           N+0
HETATM   14  C   UNK     0       0.698  -3.860   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.623  -4.651   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -1.969  -3.902   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -1.994  -2.362   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -0.673  -1.571   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -3.291  -4.694   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   11                                                  
CONECT    7    2    6    8                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   18                                                  
CONECT   10    9   11                                                       
CONECT   11    6   10   12                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   18                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   19                                                  
CONECT   17   16   18                                                       
CONECT   18    9   13   17                                                  
CONECT   19   16                                                            
MASTER        0    0    0    0    0    0    0    0   19    0   44    0
END

View in JSmol

Synonyms

Value	Source
(-)-Baptifoline	HMDB
13-Hydroxyanagyrine	HMDB
Alkaloid P3?	HMDB
Baptifoline	MeSH

Chemical Formula

C₁₅H₂₀N₂O₂

Average Mass

260.3315 Da

Monoisotopic Mass

260.15248 Da

IUPAC Name

12-hydroxy-7,15-diazatetracyclo[7.7.1.0²,⁷.0¹⁰,¹⁵]heptadeca-2,4-dien-6-one

Traditional Name

12-hydroxy-7,15-diazatetracyclo[7.7.1.0²,⁷.0¹⁰,¹⁵]heptadeca-2,4-dien-6-one

CAS Registry Number

732-50-3

SMILES

OC1CCN2CC3CC(CN4C(=O)C=CC=C34)C2C1

InChI Identifier

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

InChI Key

AOOCSKCGZYCEJX-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Ammodendron argenteum O.Ktze.	Plant	KNApSAcK
Anagyris foetida	LOTUS Database	35616633
Anarthrophyllum elegans	LOTUS Database	35616633
Baptisia perfoliata	LOTUS Database	35616633
Baptisia simplicifolia	LOTUS Database	35616633
Bolusanthus speciosus	LOTUS Database	35616633
Caulophyllum thalictroides	LOTUS Database	35616633
Clathrotropis glaucophylla	Plant	KNApSAcK
Coffea arabica L.	FooDB	Shmuel Yannai Dictionary of Food Compounds with CD-ROM: Additives, Flavors, and Ingredients. Chap...
Coffea canephora	FooDB	Shmuel Yannai Dictionary of Food Compounds with CD-ROM: Additives, Flavors, and Ingredients. Chap...
Dermatophyllum secundiflorum	LOTUS Database	35616633
Dicraeopetalum stipulare	LOTUS Database	35616633
Echinosophora koreensis	LOTUS Database	35616633
Euchresta japonica	LOTUS Database	35616633
Genista lobelii	LOTUS Database	35616633
Genista lydia	LOTUS Database	35616633
Genista pilosa	LOTUS Database	35616633
Laburnum watereri	Plant	KNApSAcK
Lamprolobium fruticosum	Plant	KNApSAcK
Lamprolobium grandiflorum	LOTUS Database	35616633
Lupinus shockleyi	LOTUS Database	35616633
Maackia amurensis	LOTUS Database	35616633
Maackia tenuifolia	LOTUS Database	35616633
Petteria ramentacea	Plant	KNApSAcK
Plagiocarpus axillaris	LOTUS Database	35616633
Platycelyphium voense	LOTUS Database	35616633
Retama monosperma	LOTUS Database	35616633
Retama spp.	Plant	KNApSAcK
Sophora alopecuroides	LOTUS Database	35616633
Sophora chrysophylla	LOTUS Database	35616633
Sophora flavescens	LOTUS Database	35616633
Sophora macrocarpa	LOTUS Database	35616633
Sophora tetraptera	LOTUS Database	35616633
Sophora tomentosa	LOTUS Database	35616633
Sophora tonkinensis	LOTUS Database	35616633
Spartium junceum	Plant	KNApSAcK
Thermopsis alterniflora Rgl.	Plant	KNApSAcK
Thermopsis chinensis	LOTUS Database	35616633
Thermopsis licentiana	Plant	KNApSAcK
Ulex airensis	Plant	KNApSAcK
Ulex australis	Plant	KNApSAcK
Ulex densus	Plant	KNApSAcK
Ulex minor	Plant	KNApSAcK
Ulex parviflorus	LOTUS Database	35616633
Ulex parviflorus subsp. jussiaei	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as anagyrine-type alkaloids. These are lupin alkaloids with a structure based on the anagyrine skeleton. Anagyrine is a tetracyclic ketone containing a quinolizidine, and two pyridine rings fused together to form dipyrido[1,2-a:1',2'-E][1,5]diazocin-4-one.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Lupin alkaloids

Sub Class

Anagyrine-type alkaloids

Direct Parent

Anagyrine-type alkaloids

Alternative Parents

Substituents

Anagyrine-type alkaloid
Quinolizidine
Pyridinone
Aralkylamine
Piperidine
Pyridine
Heteroaromatic compound
Lactam
Secondary alcohol
Tertiary aliphatic amine
Tertiary amine
Azacycle
Organoheterocyclic compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organooxygen compound
Organonitrogen compound
Organic oxygen compound
Organic nitrogen compound
Alcohol
Amine
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	1.2	ALOGPS
logP	-0.52	ChemAxon
logS	-1.1	ALOGPS
pKa (Strongest Acidic)	15.17	ChemAxon
pKa (Strongest Basic)	8.67	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	75.62 m³·mol⁻¹	ChemAxon
Polarizability	27.89 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0033481

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

621307

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Baptifoline (NP0047656)

MOL for NP0047656 (Baptifoline)

3D MOL for NP0047656 (Baptifoline)

3D SDF for NP0047656 (Baptifoline)

3D-SDF for NP0047656 (Baptifoline)

PDB for NP0047656 (Baptifoline)

3D PDB for NP0047656 (Baptifoline)

SMILES for NP0047656 (Baptifoline)

INCHI for NP0047656 (Baptifoline)

Structure for NP0047656 (Baptifoline)

3D Structure for NP0047656 (Baptifoline)