NP-MRD: Showing NP-Card for (+)-3-Epibuphanisine (NP0069862)

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Record Information

Version

2.0

Created at

2022-04-28 15:10:55 UTC

Updated at

2022-04-28 15:10:55 UTC

NP-MRD ID

NP0069862

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(+)-3-Epibuphanisine

Description

(+)-Buphanisine belongs to the class of organic compounds known as crinine- and haemanthamine-type amaryllidaceae alkaloids. These are amaryllidaceae alkaloids compounds with a structure based on the crinine or haemanthamine backbone. Both backbones have a common 5,10b-ethano bridge moiety in their frameworks, which is a very significant taxonomic feature, and the configurations of the 5,10b-ethano bridge are opposite to each other. (+)-3-Epibuphanisine is found in Crinum moorei and Sternbergia sicula. (+)-3-Epibuphanisine was first documented in 2013 (PMID: 23788411). Based on a literature review a small amount of articles have been published on (+)-Buphanisine.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 40 44  0  0  0  0  0  0  0  0999 V2000
    4.8824    1.4097    0.4785 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1565    0.7520   -0.4912 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8111    0.6977   -0.0801 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0140    1.2932   -1.1796 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8365    0.8118   -1.4990 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1781   -0.3064   -0.8629 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1574   -1.5659   -1.7073 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5336   -2.6497   -0.7307 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3913   -2.0587    0.5978 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9731   -2.0212    1.0051 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7397   -0.8518    0.5351 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9956   -0.6500    1.0366 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7021    0.4504    0.5876 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1718    1.3249   -0.3352 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8893    1.0913   -0.8270 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2043    0.0095   -0.3807 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1056    2.3357   -0.6000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9696    2.3275    0.5435 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9801    0.9613    0.8716 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9283   -0.7471    0.3722 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3915   -0.7702    0.0600 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5373    2.4508    0.6620 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8311    0.7916    1.4031 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9487    1.4821    0.2014 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6758    1.1806    0.8872 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4452    2.1673   -1.7316 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3003    1.3068   -2.3400 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8978   -1.7369   -2.0042 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8466   -1.5031   -2.5644 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5506   -3.0091   -0.9066 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1963   -3.5033   -0.7559 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0798   -2.1013    2.1262 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4817   -2.9290    0.5886 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4629   -1.3006    1.7609 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4796    1.8007   -1.5642 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4203    2.8781    1.3303 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9583    2.7450    0.3190 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7522   -0.0578    1.2248 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0035   -1.2898    0.8076 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5359   -1.2160   -0.9473 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3 21  1  0
 21 20  1  0
 20  9  1  0
  9  8  1  0
  8  7  1  0
  6  7  1  6
  6  5  1  0
  5  4  2  0
  6 16  1  0
 16 15  2  0
 15 14  1  0
 14 13  2  0
 13 19  1  0
 19 18  1  0
 18 17  1  0
 13 12  1  0
 12 11  2  0
 11 10  1  0
  4  3  1  0
 11 16  1  0
  6 20  1  0
 17 14  1  0
 10  9  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  3 25  1  1
 21 39  1  0
 21 40  1  0
 20 38  1  1
  8 30  1  0
  8 31  1  0
  7 28  1  0
  7 29  1  0
  5 27  1  0
  4 26  1  0
 15 35  1  0
 18 36  1  0
 18 37  1  0
 12 34  1  0
 10 32  1  0
 10 33  1  0
M  END


  Mrv1652304282217102D          

 21 25  0  0  1  0            999 V2000
    0.3182    0.6115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0090   -0.1534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4142   -0.8720    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2287   -1.0032    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9418   -0.5038    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5788   -0.8137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2651   -0.3559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2118    0.4674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5277    0.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7858    0.3750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1089    0.8466    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9945    0.0296    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6449   -0.4780    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4096   -0.1686    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5241    0.6485    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8737    1.1561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0600   -0.6762    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9456   -1.4932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9783    0.7725    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5053    0.1378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0646   -0.5596    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
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  5 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11  1  1  1  0  0  0
 11 12  1  0  0  0  0
 12  3  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
 11 16  1  0  0  0  0
 14 17  1  6  0  0  0
 17 18  1  0  0  0  0
  8 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
  7 21  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0069862

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CO[C@@H]1C[C@@H]2N3CC[C@@]2(C=C1)C1=CC2=C(OCO2)C=C1C3

> <INCHI_IDENTIFIER>
InChI=1S/C17H19NO3/c1-19-12-2-3-17-4-5-18(16(17)7-12)9-11-6-14-15(8-13(11)17)21-10-20-14/h2-3,6,8,12,16H,4-5,7,9-10H2,1H3/t12-,16-,17-/m0/s1

> <INCHI_KEY>
HATSAIPBKRRCME-ZLIFDBKOSA-N

> <FORMULA>
C17H19NO3

> <MOLECULAR_WEIGHT>
285.343

> <EXACT_MASS>
285.136493476

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
40

> <JCHEM_AVERAGE_POLARIZABILITY>
31.194648486197384

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,13S,15R)-15-methoxy-5,7-dioxa-12-azapentacyclo[10.5.2.0^{1,13}.0^{2,10}.0^{4,8}]nonadeca-2,4(8),9,16-tetraene

> <ALOGPS_LOGP>
1.58

> <JCHEM_LOGP>
1.7447453063333334

> <ALOGPS_LOGS>
-2.32

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
8.979117557406028

> <JCHEM_POLAR_SURFACE_AREA>
30.930000000000003

> <JCHEM_REFRACTIVITY>
79.8966

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.38e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,13S,15R)-15-methoxy-5,7-dioxa-12-azapentacyclo[10.5.2.0^{1,13}.0^{2,10}.0^{4,8}]nonadeca-2,4(8),9,16-tetraene

> <JCHEM_VEBER_RULE>
1

$$$$

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       0.594   1.141   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.017  -0.286   0.000  0.00  0.00           C+0
HETATM    3  N   UNK     0       0.773  -1.628   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0       2.294  -1.873   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.625  -0.940   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.814  -1.519   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.095  -0.664   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.995   0.872   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.718   1.746   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.334   0.700   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.070   1.580   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.856   0.055   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.070  -0.892   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.498  -0.315   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.712   1.210   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.498   2.158   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       5.712  -1.262   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       5.498  -2.787   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       7.426   1.442   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       8.410   0.257   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       7.587  -1.045   0.000  0.00  0.00           O+0
CONECT    1    2   11                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4   12                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   10                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   21                                                  
CONECT    8    7    9   19                                                  
CONECT    9    8   10                                                       
CONECT   10    9    5   11                                                  
CONECT   11   10    1   12   16                                             
CONECT   12   11    3   13                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   17                                                  
CONECT   15   14   16                                                       
CONECT   16   15   11                                                       
CONECT   17   14   18                                                       
CONECT   18   17                                                            
CONECT   19    8   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20    7                                                       
MASTER        0    0    0    0    0    0    0    0   21    0   50    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₇H₁₉NO₃

Average Mass

285.3430 Da

Monoisotopic Mass

285.13649 Da

IUPAC Name

(1R,13S,15R)-15-methoxy-5,7-dioxa-12-azapentacyclo[10.5.2.0^{1,13}.0^{2,10}.0^{4,8}]nonadeca-2,4(8),9,16-tetraene

Traditional Name

(1R,13S,15R)-15-methoxy-5,7-dioxa-12-azapentacyclo[10.5.2.0^{1,13}.0^{2,10}.0^{4,8}]nonadeca-2,4(8),9,16-tetraene

CAS Registry Number

Not Available

SMILES

CO[C@@H]1C[C@@H]2N3CC[C@@]2(C=C1)C1=CC2=C(OCO2)C=C1C3

InChI Identifier

InChI=1S/C17H19NO3/c1-19-12-2-3-17-4-5-18(16(17)7-12)9-11-6-14-15(8-13(11)17)21-10-20-14/h2-3,6,8,12,16H,4-5,7,9-10H2,1H3/t12-,16-,17-/m0/s1

InChI Key

HATSAIPBKRRCME-ZLIFDBKOSA-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
Crinum moorei	Plant	KNApSAcK
Sternbergia sicula	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as crinine- and haemanthamine-type amaryllidaceae alkaloids. These are amaryllidaceae alkaloids compounds with a structure based on the crinine or haemanthamine backbone. Both backbones have a common 5,10b-ethano bridge moiety in their frameworks, which is a very significant taxonomic feature, and the configurations of the 5,10b-ethano bridge are opposite to each other.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Amaryllidaceae alkaloids

Sub Class

Crinine- and Haemanthamine-type amaryllidaceae alkaloids

Direct Parent

Crinine- and Haemanthamine-type amaryllidaceae alkaloids

Alternative Parents

Substituents

Hemanthamine/crinine alkaloid skeleton
Phenanthridine
Benzoquinoline
Benzazepine
Tetrahydroisoquinoline
Quinoline
Indole or derivatives
Benzodioxole
Aralkylamine
Azepine
Benzenoid
N-alkylpyrrolidine
Pyrrolidine
Tertiary aliphatic amine
Tertiary amine
Oxacycle
Azacycle
Organoheterocyclic compound
Ether
Dialkyl ether
Acetal
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
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	1.58	ALOGPS
logP	1.74	ChemAxon
logS	-2.3	ALOGPS
pKa (Strongest Basic)	8.98	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	30.93 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	79.9 m³·mol⁻¹	ChemAxon
Polarizability	31.19 Å³	ChemAxon
Number of Rings	5	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

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

12302150

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Wei MX, Wang CT, Du JY, Qu H, Yin PR, Bao X, Ma XY, Zhao XH, Zhang GB, Fan CA: Enantioselective synthesis of Amaryllidaceae alkaloids (+)-vittatine, (+)-epi-vittatine, and (+)-buphanisine. Chem Asian J. 2013 Sep;8(9):1966-71. doi: 10.1002/asia.201300595. Epub 2013 Jun 20. [PubMed:23788411 ]

Showing NP-Card for (+)-3-Epibuphanisine (NP0069862)

MOL for NP0069862 ((+)-3-Epibuphanisine)

3D MOL for NP0069862 ((+)-3-Epibuphanisine)

3D SDF for NP0069862 ((+)-3-Epibuphanisine)

3D-SDF for NP0069862 ((+)-3-Epibuphanisine)

PDB for NP0069862 ((+)-3-Epibuphanisine)

3D PDB for NP0069862 ((+)-3-Epibuphanisine)

SMILES for NP0069862 ((+)-3-Epibuphanisine)

INCHI for NP0069862 ((+)-3-Epibuphanisine)

Structure for NP0069862 ((+)-3-Epibuphanisine)

3D Structure for NP0069862 ((+)-3-Epibuphanisine)