NP-MRD: Showing NP-Card for (1r,2r,6r,7r,8r,9r,12e)-6-isopropyl-3,9,13-trimethyl-15-oxatricyclo[6.6.1.0²,⁷]pentadeca-3,12-dien-9-ol (NP0256582)

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Record Information

Version

2.0

Created at

2022-09-07 21:27:47 UTC

Updated at

2022-09-07 21:27:47 UTC

NP-MRD ID

NP0256582

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r,2r,6r,7r,8r,9r,12e)-6-isopropyl-3,9,13-trimethyl-15-oxatricyclo[6.6.1.0²,⁷]pentadeca-3,12-dien-9-ol

Description

(?)-Cladiella-6,11-diene-3-ol belongs to the class of organic compounds known as eunicellane and asbestinane diterpenoids. These are diterpenoids with a structure based on either the eunicellane (5,14-cyclocembrane) or the asbestinane skeleton. Based on a literature review very few articles have been published on (?)-Cladiella-6,11-diene-3-ol.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309072223272D          

 22 24  0  0  1  0            999 V2000
    3.5519    2.1595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5519    1.3345    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2664    0.9220    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2664    0.0970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5519   -0.3155    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5519   -1.1405    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2664   -1.5530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8375   -1.5530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8375    0.0970    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8375    0.9220    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3525    1.5894    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5679    1.8443    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7833    1.5894    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2984    2.2568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2984    0.9220    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2984    0.0970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7833   -0.5705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5679   -0.8254    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0830   -1.4929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0529   -1.4929    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3525   -0.5705    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6225    0.5095    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  6  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  5  9  1  0  0  0  0
  9 10  1  1  0  0  0
 10  2  1  1  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  1  0  0  0
 18 20  1  6  0  0  0
 18 21  1  0  0  0  0
  9 21  1  0  0  0  0
 21 22  1  1  0  0  0
 11 22  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0256582

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)[C@H]1CC=C(C)[C@@H]2[C@H]3C\C(C)=C/CC[C@@](C)(O)[C@H](O3)[C@H]12

> <INCHI_IDENTIFIER>
InChI=1S/C20H32O2/c1-12(2)15-9-8-14(4)17-16-11-13(3)7-6-10-20(5,21)19(22-16)18(15)17/h7-8,12,15-19,21H,6,9-11H2,1-5H3/b13-7-/t15-,16-,17-,18-,19-,20-/m1/s1

> <INCHI_KEY>
QFZNULDNHLMPKN-IWAGMHMGSA-N

> <FORMULA>
C20H32O2

> <MOLECULAR_WEIGHT>
304.474

> <EXACT_MASS>
304.24023027

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
54

> <JCHEM_AVERAGE_POLARIZABILITY>
36.12420700824952

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,2R,6R,7R,8R,9R,12E)-3,9,13-trimethyl-6-(propan-2-yl)-15-oxatricyclo[6.6.1.0^{2,7}]pentadeca-3,12-dien-9-ol

> <JCHEM_LOGP>
3.9764693973333327

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.035846490978482

> <JCHEM_PKA_STRONGEST_BASIC>
-3.220520744846011

> <JCHEM_POLAR_SURFACE_AREA>
29.46

> <JCHEM_REFRACTIVITY>
92.67699999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2R,6R,7R,8R,9R,12E)-6-isopropyl-3,9,13-trimethyl-15-oxatricyclo[6.6.1.0^{2,7}]pentadeca-3,12-dien-9-ol

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 07-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-SEP-22         0                                  
HETATM    1  C   UNK     0       6.630   4.031   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.630   2.491   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.964   1.721   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.964   0.181   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.630  -0.589   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.630  -2.129   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.964  -2.899   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.297  -2.899   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.297   0.181   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.297   1.721   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.391   2.967   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.927   3.443   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.462   2.967   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.557   4.213   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.557   1.721   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.557   0.181   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.462  -1.065   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.927  -1.541   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.022  -2.787   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       3.832  -2.787   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       4.391  -1.065   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       4.895   0.951   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   10                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6    9                                                  
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6                                                            
CONECT    9    5   10   21                                                  
CONECT   10    9    2   11                                                  
CONECT   11   10   12   22                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   20   21                                             
CONECT   19   18                                                            
CONECT   20   18                                                            
CONECT   21   18    9   22                                                  
CONECT   22   21   11                                                       
MASTER        0    0    0    0    0    0    0    0   22    0   48    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₀H₃₂O₂

Average Mass

304.4740 Da

Monoisotopic Mass

304.24023 Da

IUPAC Name

(1R,2R,6R,7R,8R,9R,12E)-3,9,13-trimethyl-6-(propan-2-yl)-15-oxatricyclo[6.6.1.0^{2,7}]pentadeca-3,12-dien-9-ol

Traditional Name

(1R,2R,6R,7R,8R,9R,12E)-6-isopropyl-3,9,13-trimethyl-15-oxatricyclo[6.6.1.0^{2,7}]pentadeca-3,12-dien-9-ol

CAS Registry Number

Not Available

SMILES

CC(C)[C@H]1CC=C(C)[C@@H]2[C@H]3C\C(C)=C/CC[C@@](C)(O)[C@H](O3)[C@H]12

InChI Identifier

InChI=1S/C20H32O2/c1-12(2)15-9-8-14(4)17-16-11-13(3)7-6-10-20(5,21)19(22-16)18(15)17/h7-8,12,15-19,21H,6,9-11H2,1-5H3/b13-7-/t15-,16-,17-,18-,19-,20-/m1/s1

InChI Key

QFZNULDNHLMPKN-IWAGMHMGSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as eunicellane and asbestinane diterpenoids. These are diterpenoids with a structure based on either the eunicellane (5,14-cyclocembrane) or the asbestinane skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Eunicellane and asbestinane diterpenoids

Alternative Parents

Substituents

Cladiellane diterpenoid
Eunicellane-type diterpenoid
Tertiary alcohol
Oxolane
Oxacycle
Organoheterocyclic compound
Ether
Dialkyl ether
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
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	3.98	ChemAxon
pKa (Strongest Acidic)	14.04	ChemAxon
pKa (Strongest Basic)	-3.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	29.46 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	92.68 m³·mol⁻¹	ChemAxon
Polarizability	36.12 Å³	ChemAxon
Number of Rings	3	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

13090250

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Bracket

METLIN ID

Not Available

PubChem Compound

20284252

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,6r,7r,8r,9r,12e)-6-isopropyl-3,9,13-trimethyl-15-oxatricyclo[6.6.1.0²,⁷]pentadeca-3,12-dien-9-ol (NP0256582)

MOL for NP0256582 ((1r,2r,6r,7r,8r,9r,12e)-6-isopropyl-3,9,13-trimethyl-15-oxatricyclo[6.6.1.0²,⁷]pentadeca-3,12-dien-9-ol)

3D MOL for NP0256582 ((1r,2r,6r,7r,8r,9r,12e)-6-isopropyl-3,9,13-trimethyl-15-oxatricyclo[6.6.1.0²,⁷]pentadeca-3,12-dien-9-ol)

3D SDF for NP0256582 ((1r,2r,6r,7r,8r,9r,12e)-6-isopropyl-3,9,13-trimethyl-15-oxatricyclo[6.6.1.0²,⁷]pentadeca-3,12-dien-9-ol)

3D-SDF for NP0256582 ((1r,2r,6r,7r,8r,9r,12e)-6-isopropyl-3,9,13-trimethyl-15-oxatricyclo[6.6.1.0²,⁷]pentadeca-3,12-dien-9-ol)

PDB for NP0256582 ((1r,2r,6r,7r,8r,9r,12e)-6-isopropyl-3,9,13-trimethyl-15-oxatricyclo[6.6.1.0²,⁷]pentadeca-3,12-dien-9-ol)

3D PDB for NP0256582 ((1r,2r,6r,7r,8r,9r,12e)-6-isopropyl-3,9,13-trimethyl-15-oxatricyclo[6.6.1.0²,⁷]pentadeca-3,12-dien-9-ol)

SMILES for NP0256582 ((1r,2r,6r,7r,8r,9r,12e)-6-isopropyl-3,9,13-trimethyl-15-oxatricyclo[6.6.1.0²,⁷]pentadeca-3,12-dien-9-ol)

INCHI for NP0256582 ((1r,2r,6r,7r,8r,9r,12e)-6-isopropyl-3,9,13-trimethyl-15-oxatricyclo[6.6.1.0²,⁷]pentadeca-3,12-dien-9-ol)

Structure for NP0256582 ((1r,2r,6r,7r,8r,9r,12e)-6-isopropyl-3,9,13-trimethyl-15-oxatricyclo[6.6.1.0²,⁷]pentadeca-3,12-dien-9-ol)

3D Structure for NP0256582 ((1r,2r,6r,7r,8r,9r,12e)-6-isopropyl-3,9,13-trimethyl-15-oxatricyclo[6.6.1.0²,⁷]pentadeca-3,12-dien-9-ol)