NP-MRD: Showing NP-Card for Supinine (NP0046422)

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Record Information

Version

2.0

Created at

2022-03-17 20:00:48 UTC

Updated at

2022-03-17 20:00:48 UTC

NP-MRD ID

NP0046422

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Supinine

Description

Supinine is found in Amsinckia menziesii, Anchusa milleri, Arnebia decumbens, Chromolaena odorata, Cryptantha clevelandii, Cynoglossum creticum, Cynoglossum officinale, Eupatorium cannabinum , Eupatorium fortunei, Eupatorium japonicum, Eupatorium serotinum, Eupatorium stoechadadosum, Eupatorium stoechadosmum, Heliotropium bacciferum , Heliotropium curassavicum, Heliotropium europaeum , Heliotropium hirsutissimum, Heliotropium indicum , Heliotropium supinum, Heliotropium transalpinum, Praxelis clematidea, Tournefortia sarmentosa and Tournefortia zeylanicum.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 02241221352D          

 20 21  0  0  1  0            999 V2000
   -0.1659   -1.8564    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0630   -1.0638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5091   -0.4693    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3099   -0.6674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8820   -0.0730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7372    0.7392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4650    1.1279    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0595    0.5558    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6991   -0.1863    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.2936   -0.7584    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0213   -0.3697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8766    0.4425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8638   -0.8656    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6656   -0.0647    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0620   -1.6664    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8546   -1.8953    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4675   -2.2385    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6647   -0.6674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8935    0.1252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2367   -1.2619    0.0000 C   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  2  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
  5  9  1  0  0  0  0
  9 10  1  6  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
  8 12  1  0  0  0  0
  2 13  1  0  0  0  0
 13 14  1  1  0  0  0
 13 15  1  0  0  0  0
 15 16  1  6  0  0  0
 15 17  1  0  0  0  0
 13 18  1  6  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0046422

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)[C@](O)([C@@H](C)O)C(=O)OCC1=CCN2CCC[C@@H]12

> <INCHI_IDENTIFIER>
InChI=1S/C15H25NO4/c1-10(2)15(19,11(3)17)14(18)20-9-12-6-8-16-7-4-5-13(12)16/h6,10-11,13,17,19H,4-5,7-9H2,1-3H3/t11-,13+,15+/m1/s1

> <INCHI_KEY>
DRVWTOSBCBKXOR-ZLDLUXBVSA-N

> <FORMULA>
C15H25NO4

> <MOLECULAR_WEIGHT>
283.3633

> <EXACT_MASS>
283.178358293

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
30.988678495876588

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(7aS)-2,3,5,7a-tetrahydro-1H-pyrrolizin-7-ylmethyl (2S)-2-hydroxy-2-[(1R)-1-hydroxyethyl]-3-methylbutanoate

> <ALOGPS_LOGP>
1.36

> <JCHEM_LOGP>
0.8565826193333326

> <ALOGPS_LOGS>
-0.99

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
14.8008992296846

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.3429961300961

> <JCHEM_PKA_STRONGEST_BASIC>
8.361161081322797

> <JCHEM_POLAR_SURFACE_AREA>
70

> <JCHEM_REFRACTIVITY>
76.6246

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.89e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
supinine

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  O   UNK     0      -0.310  -3.465   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       0.118  -1.986   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -0.950  -0.876   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      -2.445  -1.246   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -3.513  -0.136   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -3.243   1.380   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -4.601   2.105   0.000  0.00  0.00           C+0
HETATM    8  N   UNK     0      -5.711   1.037   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0      -5.038  -0.348   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -6.148  -1.416   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -7.506  -0.690   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -7.236   0.826   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.612  -1.616   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       1.242  -0.121   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       1.982  -3.111   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       3.462  -3.538   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       0.873  -4.179   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.107  -1.246   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.535   0.234   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.175  -2.356   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   13                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6    9                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   12                                                  
CONECT    9    8    5   10                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11    8                                                       
CONECT   13    2   14   15   18                                             
CONECT   14   13                                                            
CONECT   15   13   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15                                                            
CONECT   18   13   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   42    0
END

View in JSmol

Synonyms

Value	Source
Spinin	MeSH

Chemical Formula

C₁₅H₂₅NO₄

Average Mass

283.3633 Da

Monoisotopic Mass

283.17836 Da

IUPAC Name

(7aS)-2,3,5,7a-tetrahydro-1H-pyrrolizin-7-ylmethyl (2S)-2-hydroxy-2-[(1R)-1-hydroxyethyl]-3-methylbutanoate

Traditional Name

supinine

CAS Registry Number

551-58-6

SMILES

CC(C)[C@](O)([C@@H](C)O)C(=O)OCC1=CCN2CCC[C@@H]12

InChI Identifier

InChI=1S/C15H25NO4/c1-10(2)15(19,11(3)17)14(18)20-9-12-6-8-16-7-4-5-13(12)16/h6,10-11,13,17,19H,4-5,7-9H2,1-3H3/t11-,13+,15+/m1/s1

InChI Key

DRVWTOSBCBKXOR-ZLDLUXBVSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Amsinckia menziesii	LOTUS Database	35616633
Anchusa milleri	LOTUS Database	35616633
Arnebia decumbens	Plant	KNApSAcK
Borago officinalis	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Chromolaena odorata	LOTUS Database	35616633
Cryptantha clevelandii	LOTUS Database	35616633
Cynoglossum creticum	LOTUS Database	35616633
Cynoglossum officinale	LOTUS Database	35616633
Eupatorium cannabinum	Plant	KNApSAcK
Eupatorium fortunei	LOTUS Database	35616633
Eupatorium japonicum	LOTUS Database	35616633
Eupatorium serotinum	Plant	KNApSAcK
Eupatorium stoechadadosum	Plant	KNApSAcK
Eupatorium stoechadosmum	Plant	KNApSAcK
Heliotropium bacciferum	Plant	KNApSAcK
Heliotropium curassavicum	LOTUS Database	35616633
Heliotropium europaeum	Plant	KNApSAcK
Heliotropium hirsutissimum	Plant	KNApSAcK
Heliotropium indicum	Plant	KNApSAcK
Heliotropium supinum	Plant	KNApSAcK
Heliotropium transalpinum	Plant	KNApSAcK
Praxelis clematidea	LOTUS Database	35616633
Tournefortia sarmentosa	Plant	KNApSAcK
Tournefortia zeylanicum	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

Alkaloid or derivatives
Pyrrolizine
Beta-hydroxy acid
Fatty acid ester
Hydroxy acid
Fatty acyl
N-alkylpyrrolidine
Pyrrolidine
Tertiary alcohol
Pyrroline
1,2-diol
Amino acid or derivatives
Carboxylic acid ester
Tertiary aliphatic amine
Tertiary amine
Secondary alcohol
Carboxylic acid derivative
Azacycle
Monocarboxylic acid or derivatives
Organoheterocyclic compound
Alcohol
Hydrocarbon derivative
Organic oxide
Organic nitrogen compound
Carbonyl group
Organopnictogen compound
Organic oxygen compound
Organonitrogen compound
Organooxygen compound
Amine
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

pyrrolizines (CHEBI:9361 )
Pyrrolizidine alkaloids (C10403 )

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	1.36	ALOGPS
logP	0.86	ChemAxon
logS	-0.99	ALOGPS
pKa (Strongest Acidic)	11.34	ChemAxon
pKa (Strongest Basic)	8.36	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	70 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	76.62 m³·mol⁻¹	ChemAxon
Polarizability	30.99 Å³	ChemAxon
Number of Rings	2	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

FDB004295

KNApSAcK ID

C00002121

Chemspider ID

Not Available

KEGG Compound ID

C10403

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

108053

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Supinine (NP0046422)

MOL for NP0046422 (Supinine)

3D MOL for NP0046422 (Supinine)

3D SDF for NP0046422 (Supinine)

3D-SDF for NP0046422 (Supinine)

PDB for NP0046422 (Supinine)

3D PDB for NP0046422 (Supinine)

SMILES for NP0046422 (Supinine)

INCHI for NP0046422 (Supinine)

Structure for NP0046422 (Supinine)

3D Structure for NP0046422 (Supinine)