NP-MRD: Showing NP-Card for Acetyllycopsamine (NP0046415)

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Record Information

Version

2.0

Created at

2022-03-17 20:00:41 UTC

Updated at

2022-03-17 20:00:41 UTC

NP-MRD ID

NP0046415

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Acetyllycopsamine

Description

Acetyllycopsamine is found in Amsinckia grandiflora, Amsinckia menziesii, Anchusa officinalis, Echium humile, Echium pininana, Eupatorium fortunei, Lappula myosotis, Liatris punctata, Oreocarya thyrsiflora and Symphytum officinale.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 02241221462D          

 24 25  0  0  0  0            999 V2000
   -1.5808   -3.6424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3734   -3.4135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9679   -3.9856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5716   -2.6127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3724   -2.8109    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9445   -2.2164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6012   -3.6035    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7707   -2.4145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5419   -1.6219    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1987   -3.0090    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3978   -2.8109    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1742   -3.4053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0295   -4.2175    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7572   -4.6061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3517   -4.0341    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.9914   -3.2920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5858   -2.7199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3136   -3.1085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1689   -3.9208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4725   -1.9028    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7081   -1.5923    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0571   -2.0991    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5947   -0.7752    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7697   -1.8118    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
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  4  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 12 16  1  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
 15 19  1  0  0  0  0
 17 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
  4 24  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0046415

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)C(O)(C(C)O)C(=O)OCC1=CCN2CCC(OC(C)=O)C12

> <INCHI_IDENTIFIER>
InChI=1S/C17H27NO6/c1-10(2)17(22,11(3)19)16(21)23-9-13-5-7-18-8-6-14(15(13)18)24-12(4)20/h5,10-11,14-15,19,22H,6-9H2,1-4H3

> <INCHI_KEY>
RKDOFSJTBIDAHX-UHFFFAOYSA-N

> <FORMULA>
C17H27NO6

> <MOLECULAR_WEIGHT>
341.3994

> <EXACT_MASS>
341.183837601

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
35.4047916313113

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
[1-(acetyloxy)-2,3,5,7a-tetrahydro-1H-pyrrolizin-7-yl]methyl 2,3-dihydroxy-2-(propan-2-yl)butanoate

> <ALOGPS_LOGP>
1.03

> <JCHEM_LOGP>
0.15001041666666667

> <ALOGPS_LOGS>
-1.41

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
14.800899082063157

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.34257485559295

> <JCHEM_PKA_STRONGEST_BASIC>
7.21834769958406

> <JCHEM_POLAR_SURFACE_AREA>
96.3

> <JCHEM_REFRACTIVITY>
87.09400000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.32e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[7-(acetyloxy)-5,6,7,7a-tetrahydro-3H-pyrrolizin-1-yl]methyl 2,3-dihydroxy-2-isopropylbutanoate

> <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  C   UNK     0      -2.951  -6.799   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -4.430  -6.372   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -5.540  -7.440   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -4.800  -4.877   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -6.295  -5.247   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -7.363  -4.137   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -6.722  -6.727   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -3.305  -4.507   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -2.878  -3.028   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0      -2.238  -5.617   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      -0.743  -5.247   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.325  -6.357   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.055  -7.873   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.413  -8.598   0.000  0.00  0.00           C+0
HETATM   15  N   UNK     0       2.523  -7.530   0.000  0.00  0.00           N+0
HETATM   16  C   UNK     0       1.851  -6.145   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.960  -5.077   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.319  -5.803   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.049  -7.319   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       2.749  -3.552   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       1.322  -2.972   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       0.107  -3.918   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       1.110  -1.447   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      -5.170  -3.382   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5    8   24                                             
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5                                                            
CONECT    8    4    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   16                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   19                                                  
CONECT   16   15   12   17                                                  
CONECT   17   16   18   20                                                  
CONECT   18   17   19                                                       
CONECT   19   18   15                                                       
CONECT   20   17   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21                                                            
CONECT   24    4                                                            
MASTER        0    0    0    0    0    0    0    0   24    0   50    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₇H₂₇NO₆

Average Mass

341.3994 Da

Monoisotopic Mass

341.18384 Da

IUPAC Name

[1-(acetyloxy)-2,3,5,7a-tetrahydro-1H-pyrrolizin-7-yl]methyl 2,3-dihydroxy-2-(propan-2-yl)butanoate

Traditional Name

[7-(acetyloxy)-5,6,7,7a-tetrahydro-3H-pyrrolizin-1-yl]methyl 2,3-dihydroxy-2-isopropylbutanoate

CAS Registry Number

73544-48-6

SMILES

CC(C)C(O)(C(C)O)C(=O)OCC1=CCN2CCC(OC(C)=O)C12

InChI Identifier

InChI=1S/C17H27NO6/c1-10(2)17(22,11(3)19)16(21)23-9-13-5-7-18-8-6-14(15(13)18)24-12(4)20/h5,10-11,14-15,19,22H,6-9H2,1-4H3

InChI Key

RKDOFSJTBIDAHX-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Amsinckia grandiflora	LOTUS Database	35616633
Amsinckia menziesii	LOTUS Database	35616633
Anchusa officinalis	LOTUS Database	35616633
Borago officinalis	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Echium humile	LOTUS Database	35616633
Echium pininana	LOTUS Database	35616633
Eupatorium fortunei	LOTUS Database	35616633
Lappula myosotis	LOTUS Database	35616633
Liatris punctata	LOTUS Database	35616633
Oreocarya thyrsiflora	LOTUS Database	35616633
Symphytum officinale	LOTUS Database	35616633

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

Molecular Framework

Aliphatic 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	1.03	ALOGPS
logP	0.15	ChemAxon
logS	-1.4	ALOGPS
pKa (Strongest Acidic)	11.34	ChemAxon
pKa (Strongest Basic)	7.22	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	96.3 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	87.09 m³·mol⁻¹	ChemAxon
Polarizability	35.4 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

FDB004283

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

586647

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Acetyllycopsamine (NP0046415)

MOL for NP0046415 (Acetyllycopsamine)

3D MOL for NP0046415 (Acetyllycopsamine)

3D SDF for NP0046415 (Acetyllycopsamine)

3D-SDF for NP0046415 (Acetyllycopsamine)

PDB for NP0046415 (Acetyllycopsamine)

3D PDB for NP0046415 (Acetyllycopsamine)

SMILES for NP0046415 (Acetyllycopsamine)

INCHI for NP0046415 (Acetyllycopsamine)

Structure for NP0046415 (Acetyllycopsamine)

3D Structure for NP0046415 (Acetyllycopsamine)