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Showing NP-Card for (-)-Sirenin (NP0051826)

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Record Information
Version2.0
Created at2022-04-27 23:02:45 UTC
Updated at2022-04-27 23:02:45 UTC
NP-MRD IDNP0051826
Secondary Accession NumbersNone
Natural Product Identification
Common Name(-)-Sirenin
Description(2E)-5-[(1S,6S,7R)-3-(hydroxymethyl)-7-methylbicyclo[4.1.0]Hept-2-en-7-yl]-2-methylpent-2-en-1-ol belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. (-)-Sirenin is found in Allomyces spp. and Saprolegnia ferax. Based on a literature review very few articles have been published on (2E)-5-[(1S,6S,7R)-3-(hydroxymethyl)-7-methylbicyclo[4.1.0]Hept-2-en-7-yl]-2-methylpent-2-en-1-ol.
Structure
Thumb
MOLSDFPDBSMILESInChI

MOL for NP0051826 ((-)-Sirenin)


  Mrv1652304282201022D          

 17 18  0  0  1  0            999 V2000
    0.0780    2.5452    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7344    2.4020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0166    1.6267    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4863    0.9947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7685    0.2195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2382   -0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4763   -0.8250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4763   -0.0000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1908    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9053   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9053   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1908   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6197    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3342   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7685   -1.0445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2647    3.0340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0772    2.8907    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
  6  5  1  1  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  1  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
  7 12  1  6  0  0  0
 10 13  1  0  0  0  0
 13 14  1  0  0  0  0
  6 15  1  6  0  0  0
  2 16  1  0  0  0  0
 16 17  1  0  0  0  0
M  END
Download

3D MOL for NP0051826 ((-)-Sirenin)

Download
3D SDF for NP0051826 ((-)-Sirenin)

  Mrv1652304282201022D          

 17 18  0  0  1  0            999 V2000
    0.0780    2.5452    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7344    2.4020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0166    1.6267    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4863    0.9947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7685    0.2195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2382   -0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4763   -0.8250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4763   -0.0000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1908    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9053   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9053   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1908   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6197    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3342   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7685   -1.0445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2647    3.0340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0772    2.8907    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
  6  5  1  1  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  1  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
  7 12  1  6  0  0  0
 10 13  1  0  0  0  0
 13 14  1  0  0  0  0
  6 15  1  6  0  0  0
  2 16  1  0  0  0  0
 16 17  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0051826

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C\C(CO)=C/CC[C@]1(C)[C@H]2CCC(CO)=C[C@H]12

> <INCHI_IDENTIFIER>
InChI=1S/C15H24O2/c1-11(9-16)4-3-7-15(2)13-6-5-12(10-17)8-14(13)15/h4,8,13-14,16-17H,3,5-7,9-10H2,1-2H3/b11-4+/t13-,14-,15+/m0/s1

> <INCHI_KEY>
BOEUJLMNWCJKHN-BPOZQBESSA-N

> <FORMULA>
C15H24O2

> <MOLECULAR_WEIGHT>
236.355

> <EXACT_MASS>
236.177630013

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
41

> <JCHEM_AVERAGE_POLARIZABILITY>
28.805727101553618

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2E)-5-[(1S,6S,7R)-3-(hydroxymethyl)-7-methylbicyclo[4.1.0]hept-2-en-7-yl]-2-methylpent-2-en-1-ol

> <ALOGPS_LOGP>
2.56

> <JCHEM_LOGP>
1.8998334080000008

> <ALOGPS_LOGS>
-3.24

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
16.828172383978192

> <JCHEM_PKA_STRONGEST_ACIDIC>
16.64402351692681

> <JCHEM_PKA_STRONGEST_BASIC>
-1.999157399247939

> <JCHEM_POLAR_SURFACE_AREA>
40.46

> <JCHEM_REFRACTIVITY>
72.0743

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.37e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2E)-5-[(1S,6S,7R)-3-(hydroxymethyl)-7-methylbicyclo[4.1.0]hept-2-en-7-yl]-2-methylpent-2-en-1-ol

> <JCHEM_VEBER_RULE>
0

$$$$

Download
3D-SDF for NP0051826 ((-)-Sirenin)
Download
PDB for NP0051826 ((-)-Sirenin)
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       0.146   4.751   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.371   4.484   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.898   3.037   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.908   1.857   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.434   0.410   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.445  -0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.889  -1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.889  -0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.223   0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.556  -0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.556  -1.540   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.223  -2.310   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.890   0.770   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       6.224  -0.000   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      -1.434  -1.950   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -2.361   5.663   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -3.877   5.396   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   16                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    8   15                                             
CONECT    7    6    8   12                                                  
CONECT    8    7    6    9                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   13                                                  
CONECT   11   10   12                                                       
CONECT   12   11    7                                                       
CONECT   13   10   14                                                       
CONECT   14   13                                                            
CONECT   15    6                                                            
CONECT   16    2   17                                                       
CONECT   17   16                                                            
MASTER        0    0    0    0    0    0    0    0   17    0   36    0
END

Download
3D PDB for NP0051826 ((-)-Sirenin)
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SMILES for NP0051826 ((-)-Sirenin)
C\C(CO)=C/CC[C@]1(C)[C@H]2CCC(CO)=C[C@H]12
Download
INCHI for NP0051826 ((-)-Sirenin)
InChI=1S/C15H24O2/c1-11(9-16)4-3-7-15(2)13-6-5-12(10-17)8-14(13)15/h4,8,13-14,16-17H,3,5-7,9-10H2,1-2H3/b11-4+/t13-,14-,15+/m0/s1
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View in JSmol
SynonymsNot Available
Chemical FormulaC15H24O2
Average Mass236.3550 Da
Monoisotopic Mass236.17763 Da
IUPAC Name(2E)-5-[(1S,6S,7R)-3-(hydroxymethyl)-7-methylbicyclo[4.1.0]hept-2-en-7-yl]-2-methylpent-2-en-1-ol
Traditional Name(2E)-5-[(1S,6S,7R)-3-(hydroxymethyl)-7-methylbicyclo[4.1.0]hept-2-en-7-yl]-2-methylpent-2-en-1-ol
CAS Registry NumberNot Available
SMILES
C\C(CO)=C/CC[C@]1(C)[C@H]2CCC(CO)=C[C@H]12
InChI Identifier
InChI=1S/C15H24O2/c1-11(9-16)4-3-7-15(2)13-6-5-12(10-17)8-14(13)15/h4,8,13-14,16-17H,3,5-7,9-10H2,1-2H3/b11-4+/t13-,14-,15+/m0/s1
InChI KeyBOEUJLMNWCJKHN-BPOZQBESSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Allomyces spp.Fungi
Saprolegnia feraxChromalveolata
Chemical Taxonomy
Description Belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units.
KingdomOrganic compounds  
Super ClassLipids and lipid-like molecules  
ClassPrenol lipids  
Sub ClassSesquiterpenoids  
Direct ParentSesquiterpenoids  
Alternative Parents
Substituents
  • Sesquicarane sesquiterpenoid
    • 

  • Sesquiterpenoid
    • 

  • Fatty alcohol
    • 

  • Fatty acyl
    • 

  • Organic oxygen compound
    • 

  • Hydrocarbon derivative
    • 

  • Primary alcohol
    • 

  • Organooxygen compound
    • 

  • Alcohol
    • 

  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External DescriptorsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP2.56ALOGPS
logP1.9ChemAxon
logS-3.2ALOGPS
pKa (Strongest Acidic)16.64ChemAxon
pKa (Strongest Basic)-2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area40.46 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity72.07 m³·mol⁻¹ChemAxon
Polarizability28.81 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound12304477  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General ReferencesNot Available