NP-MRD: Showing NP-Card for (1r,2r,5s,7s,10r,13s,17s)-5-isopropyl-1,13-dimethyl-6,11-dioxapentacyclo[8.6.1.0²,⁸.0⁵,⁷.0¹³,¹⁷]heptadec-8-en-12-one (NP0325739)

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Record Information

Version

2.0

Created at

2022-09-12 06:43:38 UTC

Updated at

2022-09-12 06:43:39 UTC

NP-MRD ID

NP0325739

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r,2r,5s,7s,10r,13s,17s)-5-isopropyl-1,13-dimethyl-6,11-dioxapentacyclo[8.6.1.0²,⁸.0⁵,⁷.0¹³,¹⁷]heptadec-8-en-12-one

Description

(1R,2R,5S,7S,10R,13S,17S)-1,13-dimethyl-5-(propan-2-yl)-6,11-dioxapentacyclo[8.6.1.0²,⁸.0⁵,⁷.0¹³,¹⁷]Heptadec-8-en-12-one belongs to the class of organic compounds known as naphthofurans. Naphthofurans are compounds containing a furan ring fused to a naphthalene moiety. Furan is a 5 membered- ring aromatic ring with four carbon and one oxygen atoms. Naphthalene is a polycyclic aromatic hydrocarbon made up of two fused benzene rings. (1r,2r,5s,7s,10r,13s,17s)-5-isopropyl-1,13-dimethyl-6,11-dioxapentacyclo[8.6.1.0²,⁸.0⁵,⁷.0¹³,¹⁷]heptadec-8-en-12-one is found in Juniperus chinensis. Based on a literature review very few articles have been published on (1R,2R,5S,7S,10R,13S,17S)-1,13-dimethyl-5-(propan-2-yl)-6,11-dioxapentacyclo[8.6.1.0²,⁸.0⁵,⁷.0¹³,¹⁷]Heptadec-8-en-12-one.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309122208432D          

 23 27  0  0  1  0            999 V2000
    6.4082    1.7623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6541    2.0969    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5667    2.9172    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9872    1.6111    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.5015    2.2779    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6811    2.1906    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3465    1.4365    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.8323    0.7697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4977    0.0155    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6774   -0.0718    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1933   -0.7398    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4084   -0.4859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7415   -0.9717    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4073    0.3391    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6540    0.0025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7935    0.8903    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9639    1.6975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7482    1.9535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5261    1.3492    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7519    2.1427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1916    0.5950    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.6527    0.8570    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.4730    0.9443    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
  4  2  1  6  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  7  6  1  1  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  1  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  6  0  0  0
 14 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
  7 19  1  0  0  0  0
 19 20  1  1  0  0  0
 19 21  1  0  0  0  0
 21 10  1  6  0  0  0
 14 21  1  0  0  0  0
  8 22  1  0  0  0  0
  4 22  1  0  0  0  0
 22 23  1  1  0  0  0
  4 23  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0325739

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)[C@@]12CC[C@H]3C(=C[C@H]4OC(=O)[C@@]5(C)CCC[C@@]3(C)[C@H]45)[C@@H]1O2

> <INCHI_IDENTIFIER>
InChI=1S/C20H28O3/c1-11(2)20-9-6-13-12(16(20)23-20)10-14-15-18(13,3)7-5-8-19(15,4)17(21)22-14/h10-11,13-16H,5-9H2,1-4H3/t13-,14+,15-,16-,18+,19-,20-/m0/s1

> <INCHI_KEY>
LCMPHUFXGRWSHE-ZUJGYIQBSA-N

> <FORMULA>
C20H28O3

> <MOLECULAR_WEIGHT>
316.441

> <EXACT_MASS>
316.203844762

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
51

> <JCHEM_AVERAGE_POLARIZABILITY>
36.07676032084517

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,2R,5S,7S,10R,13S,17S)-1,13-dimethyl-5-(propan-2-yl)-6,11-dioxapentacyclo[8.6.1.0^{2,8}.0^{5,7}.0^{13,17}]heptadec-8-en-12-one

> <JCHEM_LOGP>
3.8752122596666663

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.259689566495186

> <JCHEM_POLAR_SURFACE_AREA>
38.83

> <JCHEM_REFRACTIVITY>
87.61300000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2R,5S,7S,10R,13S,17S)-5-isopropyl-1,13-dimethyl-6,11-dioxapentacyclo[8.6.1.0^{2,8}.0^{5,7}.0^{13,17}]heptadec-8-en-12-one

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 12-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-SEP-22         0                                  
HETATM    1  C   UNK     0      11.962   3.290   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      10.554   3.914   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      10.391   5.445   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.310   3.007   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.403   4.252   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.871   4.089   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.247   2.681   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.154   1.437   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.529   0.029   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.998  -0.134   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       4.094  -1.381   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       2.629  -0.907   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       1.384  -1.814   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       2.627   0.633   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.221   0.005   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.481   1.662   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.799   3.169   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.263   3.646   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.715   2.518   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.137   4.000   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.091   1.111   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       8.685   1.600   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      10.216   1.763   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5   22   23                                             
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8   19                                                  
CONECT    8    7    9   22                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   21                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15   16   21                                             
CONECT   15   14                                                            
CONECT   16   14   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18    7   20   21                                             
CONECT   20   19                                                            
CONECT   21   19   10   14                                                  
CONECT   22    8    4   23                                                  
CONECT   23   22    4                                                       
MASTER        0    0    0    0    0    0    0    0   23    0   54    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₀H₂₈O₃

Average Mass

316.4410 Da

Monoisotopic Mass

316.20384 Da

IUPAC Name

(1R,2R,5S,7S,10R,13S,17S)-1,13-dimethyl-5-(propan-2-yl)-6,11-dioxapentacyclo[8.6.1.0^{2,8}.0^{5,7}.0^{13,17}]heptadec-8-en-12-one

Traditional Name

(1R,2R,5S,7S,10R,13S,17S)-5-isopropyl-1,13-dimethyl-6,11-dioxapentacyclo[8.6.1.0^{2,8}.0^{5,7}.0^{13,17}]heptadec-8-en-12-one

CAS Registry Number

Not Available

SMILES

CC(C)[C@@]12CC[C@H]3C(=C[C@H]4OC(=O)[C@@]5(C)CCC[C@@]3(C)[C@H]45)[C@@H]1O2

InChI Identifier

InChI=1S/C20H28O3/c1-11(2)20-9-6-13-12(16(20)23-20)10-14-15-18(13,3)7-5-8-19(15,4)17(21)22-14/h10-11,13-16H,5-9H2,1-4H3/t13-,14+,15-,16-,18+,19-,20-/m0/s1

InChI Key

LCMPHUFXGRWSHE-ZUJGYIQBSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Juniperus chinensis	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as naphthofurans. Naphthofurans are compounds containing a furan ring fused to a naphthalene moiety. Furan is a 5 membered- ring aromatic ring with four carbon and one oxygen atoms. Naphthalene is a polycyclic aromatic hydrocarbon made up of two fused benzene rings.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Naphthofurans

Sub Class

Not Available

Direct Parent

Naphthofurans

Alternative Parents

Substituents

Naphthofuran
Oxepane
Gamma butyrolactone
Tetrahydrofuran
Carboxylic acid ester
Lactone
Carboxylic acid derivative
Dialkyl ether
Oxirane
Ether
Monocarboxylic acid or derivatives
Oxacycle
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Carbonyl group
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	3.88	ChemAxon
pKa (Strongest Basic)	-4.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	38.83 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	87.61 m³·mol⁻¹	ChemAxon
Polarizability	36.08 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	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

162910805

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1r,2r,5s,7s,10r,13s,17s)-5-isopropyl-1,13-dimethyl-6,11-dioxapentacyclo[8.6.1.0²,⁸.0⁵,⁷.0¹³,¹⁷]heptadec-8-en-12-one (NP0325739)

MOL for NP0325739 ((1r,2r,5s,7s,10r,13s,17s)-5-isopropyl-1,13-dimethyl-6,11-dioxapentacyclo[8.6.1.0²,⁸.0⁵,⁷.0¹³,¹⁷]heptadec-8-en-12-one)

3D MOL for NP0325739 ((1r,2r,5s,7s,10r,13s,17s)-5-isopropyl-1,13-dimethyl-6,11-dioxapentacyclo[8.6.1.0²,⁸.0⁵,⁷.0¹³,¹⁷]heptadec-8-en-12-one)

3D SDF for NP0325739 ((1r,2r,5s,7s,10r,13s,17s)-5-isopropyl-1,13-dimethyl-6,11-dioxapentacyclo[8.6.1.0²,⁸.0⁵,⁷.0¹³,¹⁷]heptadec-8-en-12-one)

3D-SDF for NP0325739 ((1r,2r,5s,7s,10r,13s,17s)-5-isopropyl-1,13-dimethyl-6,11-dioxapentacyclo[8.6.1.0²,⁸.0⁵,⁷.0¹³,¹⁷]heptadec-8-en-12-one)

PDB for NP0325739 ((1r,2r,5s,7s,10r,13s,17s)-5-isopropyl-1,13-dimethyl-6,11-dioxapentacyclo[8.6.1.0²,⁸.0⁵,⁷.0¹³,¹⁷]heptadec-8-en-12-one)

3D PDB for NP0325739 ((1r,2r,5s,7s,10r,13s,17s)-5-isopropyl-1,13-dimethyl-6,11-dioxapentacyclo[8.6.1.0²,⁸.0⁵,⁷.0¹³,¹⁷]heptadec-8-en-12-one)

SMILES for NP0325739 ((1r,2r,5s,7s,10r,13s,17s)-5-isopropyl-1,13-dimethyl-6,11-dioxapentacyclo[8.6.1.0²,⁸.0⁵,⁷.0¹³,¹⁷]heptadec-8-en-12-one)

INCHI for NP0325739 ((1r,2r,5s,7s,10r,13s,17s)-5-isopropyl-1,13-dimethyl-6,11-dioxapentacyclo[8.6.1.0²,⁸.0⁵,⁷.0¹³,¹⁷]heptadec-8-en-12-one)

Structure for NP0325739 ((1r,2r,5s,7s,10r,13s,17s)-5-isopropyl-1,13-dimethyl-6,11-dioxapentacyclo[8.6.1.0²,⁸.0⁵,⁷.0¹³,¹⁷]heptadec-8-en-12-one)

3D Structure for NP0325739 ((1r,2r,5s,7s,10r,13s,17s)-5-isopropyl-1,13-dimethyl-6,11-dioxapentacyclo[8.6.1.0²,⁸.0⁵,⁷.0¹³,¹⁷]heptadec-8-en-12-one)