NP-MRD: Showing NP-Card for Dihydroprehelminthosporol (NP0066413)

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Record Information

Version

2.0

Created at

2022-04-28 10:40:34 UTC

Updated at

2022-04-28 10:40:35 UTC

NP-MRD ID

NP0066413

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Dihydroprehelminthosporol

Description

[(1R,4R,5S,6R,8R)-6-(hydroxymethyl)-1-methyl-7-methylidene-4-(propan-2-yl)bicyclo[3.2.1]Octan-8-yl]methanol belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. Dihydroprehelminthosporol is found in Cochliobolus sativus, Biporalis setariae, Biporalis sorokiniana, Biporalis sp., Cochlibolus setariae, Helminthosporium sativum and Sorghum halepense L.. Based on a literature review very few articles have been published on [(1R,4R,5S,6R,8R)-6-(hydroxymethyl)-1-methyl-7-methylidene-4-(propan-2-yl)bicyclo[3.2.1]Octan-8-yl]methanol.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652304282212402D          

 17 18  0  0  1  0            999 V2000
    0.1570    0.4916    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1617   -0.3334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5971   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8097   -0.8440    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6130   -0.6558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1986    0.0648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6043    0.8308    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7990    1.0097    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0361    0.0842    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8023   -0.1172    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4794   -0.7649    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0821    1.5947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8166    2.3918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9477    1.7116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5534   -1.6742    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6033    0.9142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7467    1.7501    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
  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  0  0  0  0
  8  1  1  6  0  0  0
  8  9  1  0  0  0  0
  4  9  1  0  0  0  0
  9 10  1  1  0  0  0
 10 11  1  0  0  0  0
  7 12  1  1  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
  4 15  1  6  0  0  0
  1 16  1  6  0  0  0
 16 17  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0066413

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)[C@H]1CC[C@]2(C)[C@H](CO)[C@@H]1[C@@H](CO)C2=C

> <INCHI_IDENTIFIER>
InChI=1S/C15H26O2/c1-9(2)11-5-6-15(4)10(3)12(7-16)14(11)13(15)8-17/h9,11-14,16-17H,3,5-8H2,1-2,4H3/t11-,12+,13-,14+,15+/m1/s1

> <INCHI_KEY>
KFSUHYMYSGYWGI-SEBNEYGDSA-N

> <FORMULA>
C15H26O2

> <MOLECULAR_WEIGHT>
238.371

> <EXACT_MASS>
238.193280077

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
43

> <JCHEM_AVERAGE_POLARIZABILITY>
27.37506773697284

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
[(1R,4R,5S,6R,8R)-6-(hydroxymethyl)-1-methyl-7-methylidene-4-(propan-2-yl)bicyclo[3.2.1]octan-8-yl]methanol

> <ALOGPS_LOGP>
2.21

> <JCHEM_LOGP>
1.8923399623333346

> <ALOGPS_LOGS>
-2.92

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
18.652967864752675

> <JCHEM_PKA_STRONGEST_ACIDIC>
18.217528787729627

> <JCHEM_PKA_STRONGEST_BASIC>
-0.984834096207381

> <JCHEM_POLAR_SURFACE_AREA>
40.46

> <JCHEM_REFRACTIVITY>
70.201

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.87e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[(1R,4R,5S,6R,8R)-6-(hydroxymethyl)-4-isopropyl-1-methyl-7-methylidenebicyclo[3.2.1]octan-8-yl]methanol

> <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       0.293   0.918   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.302  -0.622   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.115  -1.400   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.511  -1.576   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.011  -1.224   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.104   0.121   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.995   1.551   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.491   1.885   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.934   0.157   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.364  -0.219   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       4.628  -1.428   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       3.887   2.977   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.391   4.465   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.502   3.195   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.033  -3.125   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -1.126   1.707   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -1.394   3.267   0.000  0.00  0.00           O+0
CONECT    1    2    8   16                                                  
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5    9   15                                             
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8   12                                                  
CONECT    8    7    1    9                                                  
CONECT    9    8    4   10                                                  
CONECT   10    9   11                                                       
CONECT   11   10                                                            
CONECT   12    7   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12                                                            
CONECT   15    4                                                            
CONECT   16    1   17                                                       
CONECT   17   16                                                            
MASTER        0    0    0    0    0    0    0    0   17    0   36    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₅H₂₆O₂

Average Mass

238.3710 Da

Monoisotopic Mass

238.19328 Da

IUPAC Name

[(1R,4R,5S,6R,8R)-6-(hydroxymethyl)-1-methyl-7-methylidene-4-(propan-2-yl)bicyclo[3.2.1]octan-8-yl]methanol

Traditional Name

[(1R,4R,5S,6R,8R)-6-(hydroxymethyl)-4-isopropyl-1-methyl-7-methylidenebicyclo[3.2.1]octan-8-yl]methanol

CAS Registry Number

Not Available

SMILES

CC(C)[C@H]1CC[C@]2(C)[C@H](CO)[C@@H]1[C@@H](CO)C2=C

InChI Identifier

InChI=1S/C15H26O2/c1-9(2)11-5-6-15(4)10(3)12(7-16)14(11)13(15)8-17/h9,11-14,16-17H,3,5-8H2,1-2,4H3/t11-,12+,13-,14+,15+/m1/s1

InChI Key

KFSUHYMYSGYWGI-SEBNEYGDSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Bipolaris sorokiniana	Fungi	KNApSAcK
Biporalis setariae	-	KNApSAcK
Biporalis sorokiniana	-	KNApSAcK
Biporalis sp.	-	KNApSAcK
Cochlibolus setariae	-	KNApSAcK
Helminthosporium sativum	Fungi	KNApSAcK
Sorghum halepense L.	Plant	KNApSAcK

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
Organic oxygen compound
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
Alcohol
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic 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	2.21	ALOGPS
logP	1.89	ChemAxon
logS	-2.9	ALOGPS
pKa (Strongest Acidic)	18.22	ChemAxon
pKa (Strongest Basic)	-0.98	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	40.46 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	70.2 m³·mol⁻¹	ChemAxon
Polarizability	27.38 Å³	ChemAxon
Number of Rings	2	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

113610779

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

162821332

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Dihydroprehelminthosporol (NP0066413)

MOL for NP0066413 (Dihydroprehelminthosporol)

3D MOL for NP0066413 (Dihydroprehelminthosporol)

3D SDF for NP0066413 (Dihydroprehelminthosporol)

3D-SDF for NP0066413 (Dihydroprehelminthosporol)

PDB for NP0066413 (Dihydroprehelminthosporol)

3D PDB for NP0066413 (Dihydroprehelminthosporol)

SMILES for NP0066413 (Dihydroprehelminthosporol)

INCHI for NP0066413 (Dihydroprehelminthosporol)

Structure for NP0066413 (Dihydroprehelminthosporol)

3D Structure for NP0066413 (Dihydroprehelminthosporol)