NP-MRD: Showing NP-Card for 8-(3-hydroxy-3-methylpent-4-en-1-yl)-4,4,7,8a-tetramethyl-1,2,3,4a,5,8-hexahydronaphthalen-2-ol (NP0319956)

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Record Information

Version

2.0

Created at

2022-09-11 21:15:39 UTC

Updated at

2022-09-11 21:15:39 UTC

NP-MRD ID

NP0319956

Secondary Accession Numbers

None

Natural Product Identification

Common Name

8-(3-hydroxy-3-methylpent-4-en-1-yl)-4,4,7,8a-tetramethyl-1,2,3,4a,5,8-hexahydronaphthalen-2-ol

Description

8-(3-Hydroxy-3-methylpent-4-en-1-yl)-4,4,7,8a-tetramethyl-1,2,3,4,4a,5,8,8a-octahydronaphthalen-2-ol belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units. 8-(3-hydroxy-3-methylpent-4-en-1-yl)-4,4,7,8a-tetramethyl-1,2,3,4a,5,8-hexahydronaphthalen-2-ol is found in Waitzia acuminata and Zanthoxylum simulans. 8-(3-Hydroxy-3-methylpent-4-en-1-yl)-4,4,7,8a-tetramethyl-1,2,3,4,4a,5,8,8a-octahydronaphthalen-2-ol is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv1533004161522022D          

 22 23  0  0  0  0            999 V2000
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3276    0.6320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3882    0.6320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3184   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9684   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.9500    0.0000 C   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  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  6  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
  5 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
  2 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
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
 18 21  1  0  0  0  0
 21 22  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0319956

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1=CCC2C(C)(C)CC(O)CC2(C)C1CCC(C)(O)C=C

> <INCHI_IDENTIFIER>
InChI=1S/C20H34O2/c1-7-19(5,22)11-10-16-14(2)8-9-17-18(3,4)12-15(21)13-20(16,17)6/h7-8,15-17,21-22H,1,9-13H2,2-6H3

> <INCHI_KEY>
OSUUGEJSAUZHLM-UHFFFAOYSA-N

> <FORMULA>
C20H34O2

> <MOLECULAR_WEIGHT>
306.49

> <EXACT_MASS>
306.255880335

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
56

> <JCHEM_AVERAGE_POLARIZABILITY>
37.13747133963283

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
8-(3-hydroxy-3-methylpent-4-en-1-yl)-4,4,7,8a-tetramethyl-1,2,3,4,4a,5,8,8a-octahydronaphthalen-2-ol

> <ALOGPS_LOGP>
4.43

> <JCHEM_LOGP>
3.8597674056666658

> <ALOGPS_LOGS>
-4.49

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
19.36311888721961

> <JCHEM_PKA_STRONGEST_ACIDIC>
18.327628377933426

> <JCHEM_PKA_STRONGEST_BASIC>
-0.7592560696138585

> <JCHEM_POLAR_SURFACE_AREA>
40.46

> <JCHEM_REFRACTIVITY>
93.82029999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.82e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
8-(3-hydroxy-3-methylpent-4-en-1-yl)-4,4,7,8a-tetramethyl-1,2,3,4a,5,8-hexahydronaphthalen-2-ol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 16-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   16-APR-15         0                                  
HETATM    1  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.345   1.180   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.325   1.180   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       8.002  -3.080   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.001  -3.850   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.461  -6.930   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       5.541  -6.930   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       4.001  -8.470   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       5.335  -9.240   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   15                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   13                                                  
CONECT    6    5    7    8    9                                             
CONECT    7    6                                                            
CONECT    8    6                                                            
CONECT    9    6   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12    5   14   15                                             
CONECT   14   13                                                            
CONECT   15   13    2   16                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   20   21                                             
CONECT   19   18                                                            
CONECT   20   18                                                            
CONECT   21   18   22                                                       
CONECT   22   21                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   46    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₀H₃₄O₂

Average Mass

306.4900 Da

Monoisotopic Mass

306.25588 Da

IUPAC Name

8-(3-hydroxy-3-methylpent-4-en-1-yl)-4,4,7,8a-tetramethyl-1,2,3,4,4a,5,8,8a-octahydronaphthalen-2-ol

Traditional Name

8-(3-hydroxy-3-methylpent-4-en-1-yl)-4,4,7,8a-tetramethyl-1,2,3,4a,5,8-hexahydronaphthalen-2-ol

CAS Registry Number

Not Available

SMILES

CC1=CCC2C(C)(C)CC(O)CC2(C)C1CCC(C)(O)C=C

InChI Identifier

InChI=1S/C20H34O2/c1-7-19(5,22)11-10-16-14(2)8-9-17-18(3,4)12-15(21)13-20(16,17)6/h7-8,15-17,21-22H,1,9-13H2,2-6H3

InChI Key

OSUUGEJSAUZHLM-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Waitzia acuminata	LOTUS Database	35616633
Zanthoxylum simulans	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Diterpenoids

Alternative Parents

Substituents

Diterpenoid
Labdane diterpenoid
Tertiary alcohol
Cyclic alcohol
Secondary alcohol
Organic oxygen compound
Hydrocarbon derivative
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	4.43	ALOGPS
logP	3.86	ChemAxon
logS	-4.5	ALOGPS
pKa (Strongest Acidic)	18.33	ChemAxon
pKa (Strongest Basic)	-0.76	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	4	ChemAxon
Refractivity	93.82 m³·mol⁻¹	ChemAxon
Polarizability	37.14 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

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

14355862

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 8-(3-hydroxy-3-methylpent-4-en-1-yl)-4,4,7,8a-tetramethyl-1,2,3,4a,5,8-hexahydronaphthalen-2-ol (NP0319956)

MOL for NP0319956 (8-(3-hydroxy-3-methylpent-4-en-1-yl)-4,4,7,8a-tetramethyl-1,2,3,4a,5,8-hexahydronaphthalen-2-ol)

3D MOL for NP0319956 (8-(3-hydroxy-3-methylpent-4-en-1-yl)-4,4,7,8a-tetramethyl-1,2,3,4a,5,8-hexahydronaphthalen-2-ol)

3D SDF for NP0319956 (8-(3-hydroxy-3-methylpent-4-en-1-yl)-4,4,7,8a-tetramethyl-1,2,3,4a,5,8-hexahydronaphthalen-2-ol)

3D-SDF for NP0319956 (8-(3-hydroxy-3-methylpent-4-en-1-yl)-4,4,7,8a-tetramethyl-1,2,3,4a,5,8-hexahydronaphthalen-2-ol)

PDB for NP0319956 (8-(3-hydroxy-3-methylpent-4-en-1-yl)-4,4,7,8a-tetramethyl-1,2,3,4a,5,8-hexahydronaphthalen-2-ol)

3D PDB for NP0319956 (8-(3-hydroxy-3-methylpent-4-en-1-yl)-4,4,7,8a-tetramethyl-1,2,3,4a,5,8-hexahydronaphthalen-2-ol)

SMILES for NP0319956 (8-(3-hydroxy-3-methylpent-4-en-1-yl)-4,4,7,8a-tetramethyl-1,2,3,4a,5,8-hexahydronaphthalen-2-ol)

INCHI for NP0319956 (8-(3-hydroxy-3-methylpent-4-en-1-yl)-4,4,7,8a-tetramethyl-1,2,3,4a,5,8-hexahydronaphthalen-2-ol)

Structure for NP0319956 (8-(3-hydroxy-3-methylpent-4-en-1-yl)-4,4,7,8a-tetramethyl-1,2,3,4a,5,8-hexahydronaphthalen-2-ol)

3D Structure for NP0319956 (8-(3-hydroxy-3-methylpent-4-en-1-yl)-4,4,7,8a-tetramethyl-1,2,3,4a,5,8-hexahydronaphthalen-2-ol)