NP-MRD: Showing NP-Card for Brunsvigine (NP0050730)

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Record Information

Version

2.0

Created at

2022-04-27 22:03:50 UTC

Updated at

2022-04-27 22:03:50 UTC

NP-MRD ID

NP0050730

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Brunsvigine

Description

Brunsvigine, also known as 3alpha-pancracine, belongs to the class of organic compounds known as alkaloids and derivatives. These are naturally occurring chemical compounds that contain mostly basic nitrogen atoms. This group also includes some related compounds with neutral and even weakly acidic properties. Also some synthetic compounds of similar structure are attributed to alkaloids. In addition to carbon, hydrogen and nitrogen, alkaloids may also contain oxygen, sulfur and more rarely other elements such as chlorine, bromine, and phosphorus. Brunsvigine is found in Brunsvigia cooperi. Brunsvigine was first documented in 2007 (PMID: 17672470). Based on a literature review a small amount of articles have been published on Brunsvigine (PMID: 33170051) (PMID: 18781802).

Structure

MOL SDF PDB SMILES InChI


  Mrv1652304282200032D          

 21 25  0  0  1  0            999 V2000
    6.0992    0.5973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4587    0.0773    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6881    0.3720    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5581    1.1866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1985    1.7066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9691    1.4120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7037    1.7874    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2878    1.2048    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9142    0.4693    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8400    1.5929    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3525    0.7712    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3091   -0.1832    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1323   -0.2377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8384    0.4943    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0747    1.2848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5083    1.8846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7056    1.6940    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4693    0.9035    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0358    0.3037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6667    0.7129    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1392    2.2938    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  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  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
  8  9  1  0  0  0  0
  1  9  1  0  0  0  0
  4 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
  3 13  1  0  0  0  0
 14 12  1  1  0  0  0
 14 15  1  0  0  0  0
 10 15  1  0  0  0  0
 15 16  2  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
 14 19  1  0  0  0  0
 18 20  1  1  0  0  0
 17 21  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0050730

> <DATABASE_NAME>
NP-MRD

> <SMILES>
O[C@@H]1C[C@@H]2N3C[C@H](C2=C[C@@H]1O)C1=C(C3)C=C2OCOC2=C1

> <INCHI_IDENTIFIER>
InChI=1S/C16H17NO4/c18-13-2-10-11-6-17(12(10)4-14(13)19)5-8-1-15-16(3-9(8)11)21-7-20-15/h1-3,11-14,18-19H,4-7H2/t11-,12-,13-,14+/m0/s1

> <INCHI_KEY>
JKZMYBLUKAMPKM-XDQVBPFNSA-N

> <FORMULA>
C16H17NO4

> <MOLECULAR_WEIGHT>
287.315

> <EXACT_MASS>
287.115758031

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
38

> <JCHEM_AVERAGE_POLARIZABILITY>
29.980290727804082

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,13S,15R,16S)-5,7-dioxa-12-azapentacyclo[10.6.1.0^{2,10}.0^{4,8}.0^{13,18}]nonadeca-2(10),3,8,17-tetraene-15,16-diol

> <ALOGPS_LOGP>
0.06

> <JCHEM_LOGP>
0.047983077333333776

> <ALOGPS_LOGS>
-1.88

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
15.112831009888556

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.630132708719849

> <JCHEM_PKA_STRONGEST_BASIC>
7.772740763926425

> <JCHEM_POLAR_SURFACE_AREA>
62.16000000000001

> <JCHEM_REFRACTIVITY>
76.2368

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.79e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,13S,15R,16S)-5,7-dioxa-12-azapentacyclo[10.6.1.0^{2,10}.0^{4,8}.0^{13,18}]nonadeca-2(10),3,8,17-tetraene-15,16-diol

> <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      11.385   1.115   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      10.190   0.144   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.751   0.694   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.508   2.215   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       9.704   3.186   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      11.142   2.636   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      12.514   3.337   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      13.604   2.249   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      12.907   0.876   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       7.168   2.973   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.258   1.440   0.000  0.00  0.00           C+0
HETATM   12  N   UNK     0       6.177  -0.342   0.000  0.00  0.00           N+0
HETATM   13  C   UNK     0       7.714  -0.444   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.298   0.923   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.739   2.398   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.682   3.518   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.184   3.162   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.743   1.687   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.800   0.567   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       1.244   1.331   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       2.127   4.282   0.000  0.00  0.00           O+0
CONECT    1    2    6    9                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4   13                                                  
CONECT    4    3    5   10                                                  
CONECT    5    4    6                                                       
CONECT    6    5    1    7                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8    1                                                       
CONECT   10    4   11   15                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12    3                                                       
CONECT   14   12   15   19                                                  
CONECT   15   14   10   16                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   21                                                  
CONECT   18   17   19   20                                                  
CONECT   19   18   14                                                       
CONECT   20   18                                                            
CONECT   21   17                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   50    0
END

View in JSmol

Synonyms

Value	Source
(-)-Brunsvigine	Kegg
3alpha-Pancracine	Kegg
3a-Pancracine	Generator
3Α-pancracine	Generator

Chemical Formula

C₁₆H₁₇NO₄

Average Mass

287.3150 Da

Monoisotopic Mass

287.11576 Da

IUPAC Name

(1S,13S,15R,16S)-5,7-dioxa-12-azapentacyclo[10.6.1.0^{2,10}.0^{4,8}.0^{13,18}]nonadeca-2(10),3,8,17-tetraene-15,16-diol

Traditional Name

(1S,13S,15R,16S)-5,7-dioxa-12-azapentacyclo[10.6.1.0^{2,10}.0^{4,8}.0^{13,18}]nonadeca-2(10),3,8,17-tetraene-15,16-diol

CAS Registry Number

Not Available

SMILES

O[C@@H]1C[C@@H]2N3C[C@H](C2=C[C@@H]1O)C1=C(C3)C=C2OCOC2=C1

InChI Identifier

InChI=1S/C16H17NO4/c18-13-2-10-11-6-17(12(10)4-14(13)19)5-8-1-15-16(3-9(8)11)21-7-20-15/h1-3,11-14,18-19H,4-7H2/t11-,12-,13-,14+/m0/s1

InChI Key

JKZMYBLUKAMPKM-XDQVBPFNSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Brunsvigia cooperi	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as alkaloids and derivatives. These are naturally occurring chemical compounds that contain mostly basic nitrogen atoms. This group also includes some related compounds with neutral and even weakly acidic properties. Also some synthetic compounds of similar structure are attributed to alkaloids. In addition to carbon, hydrogen and nitrogen, alkaloids may also contain oxygen, sulfur and more rarely other elements such as chlorine, bromine, and phosphorus.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Not Available

Sub Class

Not Available

Direct Parent

Alkaloids and derivatives

Alternative Parents

Substituents

Pancranine-skeleton
Benzazepine
Tetrahydroisoquinoline
Benzodioxole
Indole or derivatives
Alkaloid or derivatives
Aralkylamine
Azepine
Benzenoid
N-alkylpyrrolidine
Pyrrolidine
Tertiary aliphatic amine
Tertiary amine
Secondary alcohol
1,2-diol
Oxacycle
Organoheterocyclic compound
Azacycle
Acetal
Hydrocarbon derivative
Organonitrogen compound
Organic oxygen compound
Organooxygen compound
Amine
Organic nitrogen compound
Organopnictogen compound
Alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

citraconoyl group (CHEBI:3196 )

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	0.06	ALOGPS
logP	0.048	ChemAxon
logS	-1.9	ALOGPS
pKa (Strongest Acidic)	13.63	ChemAxon
pKa (Strongest Basic)	7.77	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	62.16 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	76.24 m³·mol⁻¹	ChemAxon
Polarizability	29.98 Å³	ChemAxon
Number of Rings	5	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

C00001563

Chemspider ID

390256

KEGG Compound ID

C08519

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

441587

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Hoang THX, Ho DV, Van Phan K, Le QV, Raal A, Nguyen HT: Effects of Hippeastrum reticulatum on memory, spatial learning and object recognition in a scopolamine-induced animal model of Alzheimer's disease. Pharm Biol. 2020 Dec;58(1):1098-1104. doi: 10.1080/13880209.2020.1841810. [PubMed:33170051 ]
Hong AW, Cheng TH, Raghukumar V, Sha CK: An expedient route to Montanine-type Amaryllidaceae alkaloids: total syntheses of (-)-brunsvigine and (-)-manthine. J Org Chem. 2008 Oct 3;73(19):7580-5. doi: 10.1021/jo801089y. Epub 2008 Sep 10. [PubMed:18781802 ]
Banwell MG, Kokas OJ, Willis AC: Chemoenzymatic approaches to the montanine alkaloids: a total synthesis of (+)-brunsvigine. Org Lett. 2007 Aug 30;9(18):3503-6. doi: 10.1021/ol071344y. Epub 2007 Aug 2. [PubMed:17672470 ]

Showing NP-Card for Brunsvigine (NP0050730)

MOL for NP0050730 (Brunsvigine)

3D MOL for NP0050730 (Brunsvigine)

3D SDF for NP0050730 (Brunsvigine)

3D-SDF for NP0050730 (Brunsvigine)

PDB for NP0050730 (Brunsvigine)

3D PDB for NP0050730 (Brunsvigine)

SMILES for NP0050730 (Brunsvigine)

INCHI for NP0050730 (Brunsvigine)

Structure for NP0050730 (Brunsvigine)

3D Structure for NP0050730 (Brunsvigine)