NP-MRD: Showing NP-Card for Methyl 15-hydroxy-8alpha,12alpha-epidioxiabiet-13-en-19-oate (NP0074729)

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Record Information

Version

2.0

Created at

2022-04-28 20:03:01 UTC

Updated at

2022-04-28 20:03:01 UTC

NP-MRD ID

NP0074729

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Methyl 15-hydroxy-8alpha,12alpha-epidioxiabiet-13-en-19-oate

Description

Methyl (1R,4R,5S,9S,10R,12S)-16-(2-hydroxypropan-2-yl)-5,9-dimethyl-13,14-dioxatetracyclo[10.2.2.0¹,¹⁰.0⁴,⁹]Hexadec-15-ene-5-carboxylate belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units. Methyl 15-hydroxy-8alpha,12alpha-epidioxiabiet-13-en-19-oate is found in Juniperus phoenicea . Based on a literature review very few articles have been published on methyl (1R,4R,5S,9S,10R,12S)-16-(2-hydroxypropan-2-yl)-5,9-dimethyl-13,14-dioxatetracyclo[10.2.2.0¹,¹⁰.0⁴,⁹]Hexadec-15-ene-5-carboxylate.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652304282222032D          

 26 29  0  0  1  0            999 V2000
    5.7192   -0.0513    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0621    0.6991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5837    1.3712    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.7624    1.2930    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.4195    0.5426    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.8979   -0.1295    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5460    0.4523    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.9416    1.0930    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5073    1.7811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3254    2.0096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0024    0.8507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4946    0.1874    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1724   -0.3031    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0200   -0.2487    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4560    0.4978    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2416    1.3994    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6784    0.0677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1379   -0.0519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7980   -0.7486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5587    0.8840    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0797   -0.2091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2387    1.8728    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1319    2.6908    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0006    1.5563    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6556    2.0578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5342    2.1947    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  1  0  0  0  0
  5  6  1  0  0  0  0
  1  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  4 10  1  1  0  0  0
  8 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
  7 14  1  1  0  0  0
 13 15  1  6  0  0  0
 15 16  1  0  0  0  0
  8 16  1  1  0  0  0
 12 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 17 20  1  0  0  0  0
  5 21  1  1  0  0  0
  3 22  1  1  0  0  0
 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
  3 26  1  6  0  0  0
M  END


  Mrv1652304282222032D          

 26 29  0  0  1  0            999 V2000
    5.7192   -0.0513    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0621    0.6991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5837    1.3712    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.7624    1.2930    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.4195    0.5426    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.8979   -0.1295    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5460    0.4523    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.9416    1.0930    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5073    1.7811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3254    2.0096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0024    0.8507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4946    0.1874    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1724   -0.3031    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0200   -0.2487    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4560    0.4978    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2416    1.3994    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6784    0.0677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1379   -0.0519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7980   -0.7486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5587    0.8840    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0797   -0.2091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2387    1.8728    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1319    2.6908    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0006    1.5563    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6556    2.0578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5342    2.1947    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  1  0  0  0  0
  5  6  1  0  0  0  0
  1  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  4 10  1  1  0  0  0
  8 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
  7 14  1  1  0  0  0
 13 15  1  6  0  0  0
 15 16  1  0  0  0  0
  8 16  1  1  0  0  0
 12 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 17 20  1  0  0  0  0
  5 21  1  1  0  0  0
  3 22  1  1  0  0  0
 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
  3 26  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0074729

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)[C@@]1(C)CCC[C@@]2(C)[C@H]1CC[C@]13OO[C@@H](C[C@H]21)C(=C3)C(C)(C)O

> <INCHI_IDENTIFIER>
InChI=1S/C21H32O5/c1-18(2,23)13-12-21-10-7-15-19(3,16(21)11-14(13)25-26-21)8-6-9-20(15,4)17(22)24-5/h12,14-16,23H,6-11H2,1-5H3/t14-,15+,16+,19-,20-,21+/m0/s1

> <INCHI_KEY>
IOWHRFKVRZOMCP-YPEWMDEPSA-N

> <FORMULA>
C21H32O5

> <MOLECULAR_WEIGHT>
364.482

> <EXACT_MASS>
364.22497413

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
58

> <JCHEM_AVERAGE_POLARIZABILITY>
39.60592815284151

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl (1R,4R,5S,9S,10R,12S)-16-(2-hydroxypropan-2-yl)-5,9-dimethyl-13,14-dioxatetracyclo[10.2.2.0^{1,10}.0^{4,9}]hexadec-15-ene-5-carboxylate

> <ALOGPS_LOGP>
4.02

> <JCHEM_LOGP>
3.2225474393333338

> <ALOGPS_LOGS>
-4.69

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.643872439638582

> <JCHEM_PKA_STRONGEST_BASIC>
-2.954570194902084

> <JCHEM_POLAR_SURFACE_AREA>
64.99

> <JCHEM_REFRACTIVITY>
97.35319999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.51e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl (1R,4R,5S,9S,10R,12S)-16-(2-hydroxypropan-2-yl)-5,9-dimethyl-13,14-dioxatetracyclo[10.2.2.0^{1,10}.0^{4,9}]hexadec-15-ene-5-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

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      10.676  -0.096   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      11.316   1.305   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      10.423   2.560   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.890   2.414   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.250   1.013   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.143  -0.242   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.619   0.844   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.491   2.040   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.547   3.325   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.074   3.751   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.738   1.588   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.790   0.350   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.055  -0.566   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.637  -0.464   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       4.585   0.929   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       4.184   2.612   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       1.266   0.126   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -0.257  -0.097   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.490  -1.397   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       1.043   1.650   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       7.615  -0.390   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      11.646   3.496   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      11.446   5.023   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0      13.068   2.905   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      14.291   3.841   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      10.330   4.097   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4   22   26                                             
CONECT    4    3    5   10                                                  
CONECT    5    4    6    7   21                                             
CONECT    6    5    1                                                       
CONECT    7    5    8   14                                                  
CONECT    8    7    9   11   16                                             
CONECT    9    8   10                                                       
CONECT   10    9    4                                                       
CONECT   11    8   12                                                       
CONECT   12   11   13   17                                                  
CONECT   13   12   14   15                                                  
CONECT   14   13    7                                                       
CONECT   15   13   16                                                       
CONECT   16   15    8                                                       
CONECT   17   12   18   19   20                                             
CONECT   18   17                                                            
CONECT   19   17                                                            
CONECT   20   17                                                            
CONECT   21    5                                                            
CONECT   22    3   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25                                                       
CONECT   25   24                                                            
CONECT   26    3                                                            
MASTER        0    0    0    0    0    0    0    0   26    0   58    0
END

View in JSmol

Synonyms

Value	Source
Methyl (1R,4R,5S,9S,10R,12S)-16-(2-hydroxypropan-2-yl)-5,9-dimethyl-13,14-dioxatetracyclo[10.2.2.0,.0,]hexadec-15-ene-5-carboxylic acid	Generator

Chemical Formula

C₂₁H₃₂O₅

Average Mass

364.4820 Da

Monoisotopic Mass

364.22497 Da

IUPAC Name

methyl (1R,4R,5S,9S,10R,12S)-16-(2-hydroxypropan-2-yl)-5,9-dimethyl-13,14-dioxatetracyclo[10.2.2.0^{1,10}.0^{4,9}]hexadec-15-ene-5-carboxylate

Traditional Name

methyl (1R,4R,5S,9S,10R,12S)-16-(2-hydroxypropan-2-yl)-5,9-dimethyl-13,14-dioxatetracyclo[10.2.2.0^{1,10}.0^{4,9}]hexadec-15-ene-5-carboxylate

CAS Registry Number

Not Available

SMILES

COC(=O)[C@@]1(C)CCC[C@@]2(C)[C@H]1CC[C@]13OO[C@@H](C[C@H]21)C(=C3)C(C)(C)O

InChI Identifier

InChI=1S/C21H32O5/c1-18(2,23)13-12-21-10-7-15-19(3,16(21)11-14(13)25-26-21)8-6-9-20(15,4)17(22)24-5/h12,14-16,23H,6-11H2,1-5H3/t14-,15+,16+,19-,20-,21+/m0/s1

InChI Key

IOWHRFKVRZOMCP-YPEWMDEPSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Juniperus phoenicea	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Diterpenoids

Alternative Parents

Substituents

Diterpenoid
Abietane diterpenoid
Ortho-dioxane
Methyl ester
Tertiary alcohol
Dialkyl peroxide
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
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	4.02	ALOGPS
logP	3.22	ChemAxon
logS	-4.7	ALOGPS
pKa (Strongest Acidic)	14.64	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	64.99 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	97.35 m³·mol⁻¹	ChemAxon
Polarizability	39.61 Å³	ChemAxon
Number of Rings	4	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

162975261

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Methyl 15-hydroxy-8alpha,12alpha-epidioxiabiet-13-en-19-oate (NP0074729)

MOL for NP0074729 (Methyl 15-hydroxy-8alpha,12alpha-epidioxiabiet-13-en-19-oate)

3D MOL for NP0074729 (Methyl 15-hydroxy-8alpha,12alpha-epidioxiabiet-13-en-19-oate)

3D SDF for NP0074729 (Methyl 15-hydroxy-8alpha,12alpha-epidioxiabiet-13-en-19-oate)

3D-SDF for NP0074729 (Methyl 15-hydroxy-8alpha,12alpha-epidioxiabiet-13-en-19-oate)

PDB for NP0074729 (Methyl 15-hydroxy-8alpha,12alpha-epidioxiabiet-13-en-19-oate)

3D PDB for NP0074729 (Methyl 15-hydroxy-8alpha,12alpha-epidioxiabiet-13-en-19-oate)

SMILES for NP0074729 (Methyl 15-hydroxy-8alpha,12alpha-epidioxiabiet-13-en-19-oate)

INCHI for NP0074729 (Methyl 15-hydroxy-8alpha,12alpha-epidioxiabiet-13-en-19-oate)

Structure for NP0074729 (Methyl 15-hydroxy-8alpha,12alpha-epidioxiabiet-13-en-19-oate)

3D Structure for NP0074729 (Methyl 15-hydroxy-8alpha,12alpha-epidioxiabiet-13-en-19-oate)