NP-MRD: Showing NP-Card for (2r,5r,6r,11s,14s)-6,11-dimethyl-5-[(2r)-6-methylheptan-2-yl]-9-oxatetracyclo[8.8.0.0²,⁶.0¹¹,¹⁶]octadeca-1(10),16-dien-14-ol (NP0260997)

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Record Information

Version

2.0

Created at

2022-09-08 03:19:53 UTC

Updated at

2022-09-08 03:19:53 UTC

NP-MRD ID

NP0260997

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2r,5r,6r,11s,14s)-6,11-dimethyl-5-[(2r)-6-methylheptan-2-yl]-9-oxatetracyclo[8.8.0.0²,⁶.0¹¹,¹⁶]octadeca-1(10),16-dien-14-ol

Description

9,11-Epoxy-9,11-secocholesta-5,8-diene-3beta-ol belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. (2r,5r,6r,11s,14s)-6,11-dimethyl-5-[(2r)-6-methylheptan-2-yl]-9-oxatetracyclo[8.8.0.0²,⁶.0¹¹,¹⁶]octadeca-1(10),16-dien-14-ol is found in Sinularia leptoclados. Based on a literature review very few articles have been published on 9,11-Epoxy-9,11-secocholesta-5,8-diene-3beta-ol.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309082205192D          

 29 32  0  0  1  0            999 V2000
    4.3166   -2.3455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0311   -2.7580    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0311   -3.5830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7456   -2.3455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4600   -2.7580    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1745   -2.3455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8890   -2.7580    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.8890   -3.5830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6034   -2.3455    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.6897   -1.5250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4967   -1.3535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9092   -2.0680    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.7327   -2.1173    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2076   -2.7919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9762   -3.5838    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.2128   -3.8967    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4923   -3.4949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3571   -2.6811    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.7045   -3.1857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0292   -2.7180    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   11.6824   -3.4666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5041   -3.3926    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3258   -3.3187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6726   -2.5701    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   14.4943   -2.4961    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.1977   -1.8955    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3760   -1.9694    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9012   -1.2948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0795   -1.3687    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
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  6  0  0  0
  9  7  1  1  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 12 11  1  1  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  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
 12 18  1  0  0  0  0
  9 18  1  0  0  0  0
 18 19  1  1  0  0  0
 14 20  1  0  0  0  0
 20 21  1  1  0  0  0
 20 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  1  0  0  0
 24 26  1  0  0  0  0
 26 27  1  0  0  0  0
 20 27  1  0  0  0  0
 27 28  2  0  0  0  0
 28 29  1  0  0  0  0
 13 29  1  0  0  0  0
M  END


  Mrv1652309082205192D          

 29 32  0  0  1  0            999 V2000
    4.3166   -2.3455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0311   -2.7580    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0311   -3.5830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7456   -2.3455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4600   -2.7580    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1745   -2.3455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8890   -2.7580    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.8890   -3.5830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6034   -2.3455    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.6897   -1.5250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4967   -1.3535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9092   -2.0680    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.7327   -2.1173    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2076   -2.7919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9762   -3.5838    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.2128   -3.8967    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4923   -3.4949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3571   -2.6811    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.7045   -3.1857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0292   -2.7180    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   11.6824   -3.4666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5041   -3.3926    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3258   -3.3187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6726   -2.5701    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   14.4943   -2.4961    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.1977   -1.8955    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3760   -1.9694    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9012   -1.2948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0795   -1.3687    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
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  6  0  0  0
  9  7  1  1  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 12 11  1  1  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  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
 12 18  1  0  0  0  0
  9 18  1  0  0  0  0
 18 19  1  1  0  0  0
 14 20  1  0  0  0  0
 20 21  1  1  0  0  0
 20 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  1  0  0  0
 24 26  1  0  0  0  0
 26 27  1  0  0  0  0
 20 27  1  0  0  0  0
 27 28  2  0  0  0  0
 28 29  1  0  0  0  0
 13 29  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0260997

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2C3=C(OCC[C@]12C)[C@@]1(C)CC[C@H](O)CC1=CC3

> <INCHI_IDENTIFIER>
InChI=1S/C27H44O2/c1-18(2)7-6-8-19(3)23-11-12-24-22-10-9-20-17-21(28)13-14-26(20,4)25(22)29-16-15-27(23,24)5/h9,18-19,21,23-24,28H,6-8,10-17H2,1-5H3/t19-,21+,23-,24+,26+,27-/m1/s1

> <INCHI_KEY>
KWWIDBSRZVKILE-BXAZICILSA-N

> <FORMULA>
C27H44O2

> <MOLECULAR_WEIGHT>
400.647

> <EXACT_MASS>
400.334130657

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
73

> <JCHEM_AVERAGE_POLARIZABILITY>
50.46563693198281

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R,5R,6R,11S,14S)-6,11-dimethyl-5-[(2R)-6-methylheptan-2-yl]-9-oxatetracyclo[8.8.0.0^{2,6}.0^{11,16}]octadeca-1(10),16-dien-14-ol

> <JCHEM_LOGP>
5.852463963

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
18.270302401055506

> <JCHEM_PKA_STRONGEST_BASIC>
-1.368203960666818

> <JCHEM_POLAR_SURFACE_AREA>
29.46

> <JCHEM_REFRACTIVITY>
123.63199999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(2R,5R,6R,11S,14S)-6,11-dimethyl-5-[(2R)-6-methylheptan-2-yl]-9-oxatetracyclo[8.8.0.0^{2,6}.0^{11,16}]octadeca-1(10),16-dien-14-ol

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 08-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   08-SEP-22         0                                  
HETATM    1  C   UNK     0       8.058  -4.378   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.391  -5.148   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       9.391  -6.688   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      10.725  -4.378   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      12.059  -5.148   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      13.392  -4.378   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      14.726  -5.148   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      14.726  -6.688   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      16.060  -4.378   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      16.221  -2.847   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      17.727  -2.527   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      18.497  -3.860   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      20.034  -3.952   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      20.921  -5.212   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      20.489  -6.690   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      19.064  -7.274   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      17.719  -6.524   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      17.467  -5.005   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      16.248  -5.947   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      22.455  -5.074   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      21.807  -6.471   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      23.341  -6.333   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      24.875  -6.195   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      25.522  -4.797   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      27.056  -4.659   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      24.636  -3.538   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      23.102  -3.676   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      22.215  -2.417   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      20.682  -2.555   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   18                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   18                                                  
CONECT   13   12   14   29                                                  
CONECT   14   13   15   20                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   12    9   19                                             
CONECT   19   18                                                            
CONECT   20   14   21   22   27                                             
CONECT   21   20                                                            
CONECT   22   20   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   27                                                       
CONECT   27   26   20   28                                                  
CONECT   28   27   29                                                       
CONECT   29   28   13                                                       
MASTER        0    0    0    0    0    0    0    0   29    0   64    0
END

View in JSmol

Synonyms

Value	Source
9,11-Epoxy-9,11-secocholesta-5,8-diene-3b-ol	Generator
9,11-Epoxy-9,11-secocholesta-5,8-diene-3β-ol	Generator

Chemical Formula

C₂₇H₄₄O₂

Average Mass

400.6470 Da

Monoisotopic Mass

400.33413 Da

IUPAC Name

(2R,5R,6R,11S,14S)-6,11-dimethyl-5-[(2R)-6-methylheptan-2-yl]-9-oxatetracyclo[8.8.0.0^{2,6}.0^{11,16}]octadeca-1(10),16-dien-14-ol

Traditional Name

(2R,5R,6R,11S,14S)-6,11-dimethyl-5-[(2R)-6-methylheptan-2-yl]-9-oxatetracyclo[8.8.0.0^{2,6}.0^{11,16}]octadeca-1(10),16-dien-14-ol

CAS Registry Number

Not Available

SMILES

CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2C3=C(OCC[C@]12C)[C@@]1(C)CC[C@H](O)CC1=CC3

InChI Identifier

InChI=1S/C27H44O2/c1-18(2)7-6-8-19(3)23-11-12-24-22-10-9-20-17-21(28)13-14-26(20,4)25(22)29-16-15-27(23,24)5/h9,18-19,21,23-24,28H,6-8,10-17H2,1-5H3/t19-,21+,23-,24+,26+,27-/m1/s1

InChI Key

KWWIDBSRZVKILE-BXAZICILSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Sinularia leptoclados	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Sesquiterpenoids

Alternative Parents

Substituents

Sesquiterpenoid
Cyclic alcohol
Secondary alcohol
Oxacycle
Organoheterocyclic compound
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	5.85	ChemAxon
pKa (Strongest Acidic)	18.27	ChemAxon
pKa (Strongest Basic)	-1.4	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	5	ChemAxon
Refractivity	123.63 m³·mol⁻¹	ChemAxon
Polarizability	50.47 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	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

53381440

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2r,5r,6r,11s,14s)-6,11-dimethyl-5-[(2r)-6-methylheptan-2-yl]-9-oxatetracyclo[8.8.0.0²,⁶.0¹¹,¹⁶]octadeca-1(10),16-dien-14-ol (NP0260997)

MOL for NP0260997 ((2r,5r,6r,11s,14s)-6,11-dimethyl-5-[(2r)-6-methylheptan-2-yl]-9-oxatetracyclo[8.8.0.0²,⁶.0¹¹,¹⁶]octadeca-1(10),16-dien-14-ol)

3D MOL for NP0260997 ((2r,5r,6r,11s,14s)-6,11-dimethyl-5-[(2r)-6-methylheptan-2-yl]-9-oxatetracyclo[8.8.0.0²,⁶.0¹¹,¹⁶]octadeca-1(10),16-dien-14-ol)

3D SDF for NP0260997 ((2r,5r,6r,11s,14s)-6,11-dimethyl-5-[(2r)-6-methylheptan-2-yl]-9-oxatetracyclo[8.8.0.0²,⁶.0¹¹,¹⁶]octadeca-1(10),16-dien-14-ol)

3D-SDF for NP0260997 ((2r,5r,6r,11s,14s)-6,11-dimethyl-5-[(2r)-6-methylheptan-2-yl]-9-oxatetracyclo[8.8.0.0²,⁶.0¹¹,¹⁶]octadeca-1(10),16-dien-14-ol)

PDB for NP0260997 ((2r,5r,6r,11s,14s)-6,11-dimethyl-5-[(2r)-6-methylheptan-2-yl]-9-oxatetracyclo[8.8.0.0²,⁶.0¹¹,¹⁶]octadeca-1(10),16-dien-14-ol)

3D PDB for NP0260997 ((2r,5r,6r,11s,14s)-6,11-dimethyl-5-[(2r)-6-methylheptan-2-yl]-9-oxatetracyclo[8.8.0.0²,⁶.0¹¹,¹⁶]octadeca-1(10),16-dien-14-ol)

SMILES for NP0260997 ((2r,5r,6r,11s,14s)-6,11-dimethyl-5-[(2r)-6-methylheptan-2-yl]-9-oxatetracyclo[8.8.0.0²,⁶.0¹¹,¹⁶]octadeca-1(10),16-dien-14-ol)

INCHI for NP0260997 ((2r,5r,6r,11s,14s)-6,11-dimethyl-5-[(2r)-6-methylheptan-2-yl]-9-oxatetracyclo[8.8.0.0²,⁶.0¹¹,¹⁶]octadeca-1(10),16-dien-14-ol)

Structure for NP0260997 ((2r,5r,6r,11s,14s)-6,11-dimethyl-5-[(2r)-6-methylheptan-2-yl]-9-oxatetracyclo[8.8.0.0²,⁶.0¹¹,¹⁶]octadeca-1(10),16-dien-14-ol)

3D Structure for NP0260997 ((2r,5r,6r,11s,14s)-6,11-dimethyl-5-[(2r)-6-methylheptan-2-yl]-9-oxatetracyclo[8.8.0.0²,⁶.0¹¹,¹⁶]octadeca-1(10),16-dien-14-ol)