NP-MRD: Showing NP-Card for (+)-ent-2,3-Seco-beyer-15-ene-2,3-dioic acid (NP0082309)

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Record Information

Version

2.0

Created at

2022-04-29 03:21:04 UTC

Updated at

2022-04-29 03:21:04 UTC

NP-MRD ID

NP0082309

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(+)-ent-2,3-Seco-beyer-15-ene-2,3-dioic acid

Description

2-[(1S,4R,5S,6S,9S)-5-(carboxymethyl)-5,9-dimethyltricyclo[7.2.1.0¹,⁶]Dodec-10-en-4-yl]-2-methylpropanoic acid belongs to the class of organic compounds known as dicarboxylic acids and derivatives. These are organic compounds containing exactly two carboxylic acid groups. (+)-ent-2,3-Seco-beyer-15-ene-2,3-dioic acid is found in Spirostachys africana . Based on a literature review very few articles have been published on 2-[(1S,4R,5S,6S,9S)-5-(carboxymethyl)-5,9-dimethyltricyclo[7.2.1.0¹,⁶]Dodec-10-en-4-yl]-2-methylpropanoic acid.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652304292205212D          

 24 26  0  0  1  0            999 V2000
    1.6210   -0.0685    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7663   -0.0295    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3619    0.7355    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1751    1.5792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9156    2.0371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6210    1.4802    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0353    0.6960    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8660    0.6193    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.3422    1.2946    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.0021    2.0523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1727    2.1350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1634    1.2154    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0842    0.3942    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9846    1.1362    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4638    1.8078    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3266    0.3855    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2426    2.0366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8194   -0.2044    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5094   -0.6566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2460   -0.2851    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4627   -1.4803    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5230    0.1203    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0211    1.0660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125    0.4510    0.0000 C   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  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  1  1  6  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
  6 11  1  0  0  0  0
  9 12  1  1  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
 12 17  1  0  0  0  0
  8 18  1  1  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
  8 22  1  6  0  0  0
  6 23  1  6  0  0  0
  3 23  1  0  0  0  0
  3 24  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0082309

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)([C@@H]1CC[C@@]23C[C@](C)(CC[C@H]2[C@]1(C)CC(O)=O)C=C3)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C20H30O4/c1-17(2,16(23)24)13-6-8-20-10-9-18(3,12-20)7-5-14(20)19(13,4)11-15(21)22/h9-10,13-14H,5-8,11-12H2,1-4H3,(H,21,22)(H,23,24)/t13-,14-,18+,19+,20+/m0/s1

> <INCHI_KEY>
VZEYWVSTCVDYGB-LNARHQNUSA-N

> <FORMULA>
C20H30O4

> <MOLECULAR_WEIGHT>
334.456

> <EXACT_MASS>
334.214409446

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
54

> <JCHEM_AVERAGE_POLARIZABILITY>
20.878682591513666

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-[(1S,4R,5S,6S,9S)-5-(carboxymethyl)-5,9-dimethyltricyclo[7.2.1.0^{1,6}]dodec-10-en-4-yl]-2-methylpropanoic acid

> <ALOGPS_LOGP>
3.84

> <JCHEM_LOGP>
3.95006708

> <ALOGPS_LOGS>
-4.43

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
5.0225436117006925

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.340768453740417

> <JCHEM_POLAR_SURFACE_AREA>
74.6

> <JCHEM_REFRACTIVITY>
92.09679999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.25e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-[(1S,4R,5S,6S,9S)-5-(carboxymethyl)-5,9-dimethyltricyclo[7.2.1.0^{1,6}]dodec-10-en-4-yl]-2-methylpropanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 29-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-APR-22         0                                  
HETATM    1  C   UNK     0       3.026  -0.128   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.430  -0.055   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.675   1.373   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.327   2.948   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.709   3.803   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.026   2.763   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.799   1.299   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.350   1.156   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.239   2.417   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.604   3.831   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.056   3.985   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.772   2.269   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.624   0.736   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.305   2.121   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      10.199   3.375   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       9.943   0.720   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       7.920   3.802   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.263  -0.381   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.551  -1.226   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       7.926  -0.532   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       6.464  -2.763   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       6.576   0.225   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       1.906   1.990   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -0.770   0.842   0.000  0.00  0.00           C+0
CONECT    1    2    7                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4   23   24                                             
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   11   23                                             
CONECT    7    6    1    8                                                  
CONECT    8    7    9   18   22                                             
CONECT    9    8   10   12                                                  
CONECT   10    9   11                                                       
CONECT   11   10    6                                                       
CONECT   12    9   13   14   17                                             
CONECT   13   12                                                            
CONECT   14   12   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14                                                            
CONECT   17   12                                                            
CONECT   18    8   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19                                                            
CONECT   22    8                                                            
CONECT   23    6    3                                                       
CONECT   24    3                                                            
MASTER        0    0    0    0    0    0    0    0   24    0   52    0
END

View in JSmol

Synonyms

Value	Source
2-[(1S,4R,5S,6S,9S)-5-(Carboxymethyl)-5,9-dimethyltricyclo[7.2.1.0,]dodec-10-en-4-yl]-2-methylpropanoate	Generator

Chemical Formula

C₂₀H₃₀O₄

Average Mass

334.4560 Da

Monoisotopic Mass

334.21441 Da

IUPAC Name

2-[(1S,4R,5S,6S,9S)-5-(carboxymethyl)-5,9-dimethyltricyclo[7.2.1.0^{1,6}]dodec-10-en-4-yl]-2-methylpropanoic acid

Traditional Name

2-[(1S,4R,5S,6S,9S)-5-(carboxymethyl)-5,9-dimethyltricyclo[7.2.1.0^{1,6}]dodec-10-en-4-yl]-2-methylpropanoic acid

CAS Registry Number

Not Available

SMILES

CC(C)([C@@H]1CC[C@@]23C[C@](C)(CC[C@H]2[C@]1(C)CC(O)=O)C=C3)C(O)=O

InChI Identifier

InChI=1S/C20H30O4/c1-17(2,16(23)24)13-6-8-20-10-9-18(3,12-20)7-5-14(20)19(13,4)11-15(21)22/h9-10,13-14H,5-8,11-12H2,1-4H3,(H,21,22)(H,23,24)/t13-,14-,18+,19+,20+/m0/s1

InChI Key

VZEYWVSTCVDYGB-LNARHQNUSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Spirostachys africana	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as dicarboxylic acids and derivatives. These are organic compounds containing exactly two carboxylic acid groups.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Dicarboxylic acids and derivatives

Direct Parent

Dicarboxylic acids and derivatives

Alternative Parents

Substituents

Dicarboxylic acid or derivatives
Carboxylic acid
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic 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	3.84	ALOGPS
logP	3.95	ChemAxon
logS	-4.4	ALOGPS
pKa (Strongest Acidic)	4.34	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	74.6 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	92.1 m³·mol⁻¹	ChemAxon
Polarizability	20.88 Å³	ChemAxon
Number of Rings	3	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

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

162970747

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for (+)-ent-2,3-Seco-beyer-15-ene-2,3-dioic acid (NP0082309)

MOL for NP0082309 ((+)-ent-2,3-Seco-beyer-15-ene-2,3-dioic acid)

3D MOL for NP0082309 ((+)-ent-2,3-Seco-beyer-15-ene-2,3-dioic acid)

3D SDF for NP0082309 ((+)-ent-2,3-Seco-beyer-15-ene-2,3-dioic acid)

3D-SDF for NP0082309 ((+)-ent-2,3-Seco-beyer-15-ene-2,3-dioic acid)

PDB for NP0082309 ((+)-ent-2,3-Seco-beyer-15-ene-2,3-dioic acid)

3D PDB for NP0082309 ((+)-ent-2,3-Seco-beyer-15-ene-2,3-dioic acid)

SMILES for NP0082309 ((+)-ent-2,3-Seco-beyer-15-ene-2,3-dioic acid)

INCHI for NP0082309 ((+)-ent-2,3-Seco-beyer-15-ene-2,3-dioic acid)

Structure for NP0082309 ((+)-ent-2,3-Seco-beyer-15-ene-2,3-dioic acid)

3D Structure for NP0082309 ((+)-ent-2,3-Seco-beyer-15-ene-2,3-dioic acid)