NP-MRD: Showing NP-Card for methyl 12-hydroxy-11-methyl-6-methylidene-16-oxo-15-oxapentacyclo[9.3.2.1⁵,⁸.0¹,¹⁰.0²,⁸]heptadec-2-ene-9-carboxylate (NP0221289)

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Record Information

Version

2.0

Created at

2022-09-05 22:49:46 UTC

Updated at

2022-09-05 22:49:47 UTC

NP-MRD ID

NP0221289

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl 12-hydroxy-11-methyl-6-methylidene-16-oxo-15-oxapentacyclo[9.3.2.1⁵,⁸.0¹,¹⁰.0²,⁸]heptadec-2-ene-9-carboxylate

Description

Methyl 12-hydroxy-11-methyl-6-methylidene-16-oxo-15-oxapentacyclo[9.3.2.1⁵,⁸.0¹,¹⁰.0²,⁸]Heptadec-2-ene-9-carboxylate belongs to the class of organic compounds known as terpene lactones. These are prenol lipids containing a lactone ring. methyl 12-hydroxy-11-methyl-6-methylidene-16-oxo-15-oxapentacyclo[9.3.2.1⁵,⁸.0¹,¹⁰.0²,⁸]heptadec-2-ene-9-carboxylate is found in Lygodium reticulatum. Methyl 12-hydroxy-11-methyl-6-methylidene-16-oxo-15-oxapentacyclo[9.3.2.1⁵,⁸.0¹,¹⁰.0²,⁸]Heptadec-2-ene-9-carboxylate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv1533004151514092D          

 25 29  0  0  0  0            999 V2000
    2.0524    3.6544    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0398    2.8295    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8090    2.3696    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5110    3.0485    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0857    1.4333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8212    1.0432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4049    1.7995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9896    2.4628    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0683    1.3090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8763    1.6554    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0984    0.4846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4726   -0.0530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6621    0.1011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2773    0.8309    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6079    1.5867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4899    2.4178    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8602    0.0968    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4437   -0.6661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5895   -0.6303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1951    0.1360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8546    0.4825    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4419    0.8800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7316    1.4319    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9871    0.9733    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1672    1.1734    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  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
  6 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
  7 15  1  0  0  0  0
 15 16  2  0  0  0  0
 13 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
  5 22  1  0  0  0  0
 17 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 20 24  1  0  0  0  0
 24 25  2  0  0  0  0
M  END


  Mrv1533004151514092D          

 25 29  0  0  0  0            999 V2000
    2.0524    3.6544    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0398    2.8295    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8090    2.3696    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5110    3.0485    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0857    1.4333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8212    1.0432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4049    1.7995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9896    2.4628    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0683    1.3090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8763    1.6554    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0984    0.4846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4726   -0.0530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6621    0.1011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2773    0.8309    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6079    1.5867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4899    2.4178    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8602    0.0968    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4437   -0.6661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5895   -0.6303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1951    0.1360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8546    0.4825    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4419    0.8800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7316    1.4319    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9871    0.9733    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1672    1.1734    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  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
  6 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
  7 15  1  0  0  0  0
 15 16  2  0  0  0  0
 13 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
  5 22  1  0  0  0  0
 17 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 20 24  1  0  0  0  0
 24 25  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0221289

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)C1C2C3(C)C(O)CCC2(OC3=O)C2=CCC3CC12CC3=C

> <INCHI_IDENTIFIER>
InChI=1S/C20H24O5/c1-10-8-19-9-11(10)4-5-12(19)20-7-6-13(21)18(2,17(23)25-20)15(20)14(19)16(22)24-3/h5,11,13-15,21H,1,4,6-9H2,2-3H3

> <INCHI_KEY>
CSOGGDRRRLWUTQ-UHFFFAOYSA-N

> <FORMULA>
C20H24O5

> <MOLECULAR_WEIGHT>
344.407

> <EXACT_MASS>
344.162373873

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
49

> <JCHEM_AVERAGE_POLARIZABILITY>
36.266560180439726

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl 12-hydroxy-11-methyl-6-methylidene-16-oxo-15-oxapentacyclo[9.3.2.1⁵,⁸.0¹,¹⁰.0²,⁸]heptadec-2-ene-9-carboxylate

> <ALOGPS_LOGP>
2.24

> <JCHEM_LOGP>
1.378588090000001

> <ALOGPS_LOGS>
-2.85

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.442878034561634

> <JCHEM_PKA_STRONGEST_BASIC>
-3.042485147682741

> <JCHEM_POLAR_SURFACE_AREA>
72.83000000000001

> <JCHEM_REFRACTIVITY>
89.6209

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.89e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl 12-hydroxy-11-methyl-6-methylidene-16-oxo-15-oxapentacyclo[9.3.2.1⁵,⁸.0¹,¹⁰.0²,⁸]heptadec-2-ene-9-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 15-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   15-APR-15         0                                  
HETATM    1  C   UNK     0       3.831   6.821   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       3.808   5.282   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       5.243   4.423   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       6.554   5.691   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       5.760   2.675   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.133   1.947   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.223   3.359   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.314   4.597   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.461   2.443   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      10.969   3.090   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       9.517   0.905   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.349  -0.099   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.836   0.189   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       6.118   1.551   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       6.735   2.962   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       6.514   4.513   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       5.339   0.181   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.562  -1.243   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.967  -1.177   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.231   0.254   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       3.462   0.901   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.558   1.643   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       3.232   2.673   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       1.843   1.817   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       0.312   2.190   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   22                                                  
CONECT    6    5    7   13                                                  
CONECT    7    6    8    9   15                                             
CONECT    8    7                                                            
CONECT    9    7   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12    6   14   17                                             
CONECT   14   13   15                                                       
CONECT   15   14    7   16                                                  
CONECT   16   15                                                            
CONECT   17   13   18   22                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21   24                                                  
CONECT   21   20   22                                                       
CONECT   22   21    5   17   23                                             
CONECT   23   22   24                                                       
CONECT   24   23   20   25                                                  
CONECT   25   24                                                            
MASTER        0    0    0    0    0    0    0    0   25    0   58    0
END

View in JSmol

Synonyms

Value	Source
Methyl 12-hydroxy-11-methyl-6-methylidene-16-oxo-15-oxapentacyclo[9.3.2.1,.0,.0,]heptadec-2-ene-9-carboxylic acid	Generator
Methyl 12-hydroxy-11-methyl-6-methylidene-16-oxo-15-oxapentacyclo[9.3.2.1⁵,⁸.0¹,¹⁰.0²,⁸]heptadec-2-ene-9-carboxylic acid	Generator

Chemical Formula

C₂₀H₂₄O₅

Average Mass

344.4070 Da

Monoisotopic Mass

344.16237 Da

IUPAC Name

methyl 12-hydroxy-11-methyl-6-methylidene-16-oxo-15-oxapentacyclo[9.3.2.1⁵,⁸.0¹,¹⁰.0²,⁸]heptadec-2-ene-9-carboxylate

Traditional Name

methyl 12-hydroxy-11-methyl-6-methylidene-16-oxo-15-oxapentacyclo[9.3.2.1⁵,⁸.0¹,¹⁰.0²,⁸]heptadec-2-ene-9-carboxylate

CAS Registry Number

Not Available

SMILES

COC(=O)C1C2C3(C)C(O)CCC2(OC3=O)C2=CCC3CC12CC3=C

InChI Identifier

InChI=1S/C20H24O5/c1-10-8-19-9-11(10)4-5-12(19)20-7-6-13(21)18(2,17(23)25-20)15(20)14(19)16(22)24-3/h5,11,13-15,21H,1,4,6-9H2,2-3H3

InChI Key

CSOGGDRRRLWUTQ-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Lygodium reticulatum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as terpene lactones. These are prenol lipids containing a lactone ring.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Terpene lactones

Alternative Parents

Substituents

Terpene lactone
Sesquiterpenoid
Caprolactone
Oxepane
Dicarboxylic acid or derivatives
Gamma butyrolactone
Cyclic alcohol
Methyl ester
Tetrahydrofuran
Secondary alcohol
Lactone
Carboxylic acid ester
Oxacycle
Carboxylic acid derivative
Organoheterocyclic compound
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Alcohol
Carbonyl group
Organic oxygen 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	2.24	ALOGPS
logP	1.38	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Acidic)	14.44	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	72.83 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	89.62 m³·mol⁻¹	ChemAxon
Polarizability	36.27 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

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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for methyl 12-hydroxy-11-methyl-6-methylidene-16-oxo-15-oxapentacyclo[9.3.2.1⁵,⁸.0¹,¹⁰.0²,⁸]heptadec-2-ene-9-carboxylate (NP0221289)

MOL for NP0221289 (methyl 12-hydroxy-11-methyl-6-methylidene-16-oxo-15-oxapentacyclo[9.3.2.1⁵,⁸.0¹,¹⁰.0²,⁸]heptadec-2-ene-9-carboxylate)

3D MOL for NP0221289 (methyl 12-hydroxy-11-methyl-6-methylidene-16-oxo-15-oxapentacyclo[9.3.2.1⁵,⁸.0¹,¹⁰.0²,⁸]heptadec-2-ene-9-carboxylate)

3D SDF for NP0221289 (methyl 12-hydroxy-11-methyl-6-methylidene-16-oxo-15-oxapentacyclo[9.3.2.1⁵,⁸.0¹,¹⁰.0²,⁸]heptadec-2-ene-9-carboxylate)

3D-SDF for NP0221289 (methyl 12-hydroxy-11-methyl-6-methylidene-16-oxo-15-oxapentacyclo[9.3.2.1⁵,⁸.0¹,¹⁰.0²,⁸]heptadec-2-ene-9-carboxylate)

PDB for NP0221289 (methyl 12-hydroxy-11-methyl-6-methylidene-16-oxo-15-oxapentacyclo[9.3.2.1⁵,⁸.0¹,¹⁰.0²,⁸]heptadec-2-ene-9-carboxylate)

3D PDB for NP0221289 (methyl 12-hydroxy-11-methyl-6-methylidene-16-oxo-15-oxapentacyclo[9.3.2.1⁵,⁸.0¹,¹⁰.0²,⁸]heptadec-2-ene-9-carboxylate)

SMILES for NP0221289 (methyl 12-hydroxy-11-methyl-6-methylidene-16-oxo-15-oxapentacyclo[9.3.2.1⁵,⁸.0¹,¹⁰.0²,⁸]heptadec-2-ene-9-carboxylate)

INCHI for NP0221289 (methyl 12-hydroxy-11-methyl-6-methylidene-16-oxo-15-oxapentacyclo[9.3.2.1⁵,⁸.0¹,¹⁰.0²,⁸]heptadec-2-ene-9-carboxylate)

Structure for NP0221289 (methyl 12-hydroxy-11-methyl-6-methylidene-16-oxo-15-oxapentacyclo[9.3.2.1⁵,⁸.0¹,¹⁰.0²,⁸]heptadec-2-ene-9-carboxylate)

3D Structure for NP0221289 (methyl 12-hydroxy-11-methyl-6-methylidene-16-oxo-15-oxapentacyclo[9.3.2.1⁵,⁸.0¹,¹⁰.0²,⁸]heptadec-2-ene-9-carboxylate)