NP-MRD: Showing NP-Card for 2-[(1r,3ar,12as)-3a,6,10-trimethyl-1h,2h,3h,4h,7h,8h,11h,12h,12ah-cyclopenta[11]annulen-1-yl]propan-2-ol (NP0224296)

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Record Information

Version

2.0

Created at

2022-09-06 02:37:14 UTC

Updated at

2022-09-06 02:37:14 UTC

NP-MRD ID

NP0224296

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2-[(1r,3ar,12as)-3a,6,10-trimethyl-1h,2h,3h,4h,7h,8h,11h,12h,12ah-cyclopenta[11]annulen-1-yl]propan-2-ol

Description

(3E,7E)-dolabella-3,7-dien-18-ol belongs to the class of organic compounds known as dolabellane and neodolabellane diterpenoids. These are diterpenoids with a structure based on the dolabellane skeleton (3a,6,10-trimethyl-1-(propan-2-yl)-cyclopenta[11]annulene) or the neodolabellane skeleton. 2-[(1r,3ar,12as)-3a,6,10-trimethyl-1h,2h,3h,4h,7h,8h,11h,12h,12ah-cyclopenta[11]annulen-1-yl]propan-2-ol is found in Aglaia odorata and Dictyota dichotoma. Based on a literature review very few articles have been published on (3E,7E)-dolabella-3,7-dien-18-ol.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309062204372D          

 21 22  0  0  1  0            999 V2000
    3.2421   -3.9478    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3573   -3.1308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7074   -2.6226    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9423   -2.9314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2924   -2.4232    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0925   -3.2236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4799   -2.5661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0929   -1.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6663   -1.2443    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5234   -0.4317    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3804    0.3808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3359   -0.2888    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2892   -0.5746    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4076   -1.6062    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2294   -1.2324    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5913   -0.4910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4082   -0.6062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9816   -0.0130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5511   -1.4187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2375   -2.0052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1223   -2.8221    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  6  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  1  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
 10 13  1  0  0  0  0
  9 14  1  0  0  0  0
  5 14  1  0  0  0  0
 14 15  1  6  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
  2 21  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0224296

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C\C1=C/C[C@@]2(C)CC[C@H]([C@@H]2CC\C(C)=C\CC1)C(C)(C)O

> <INCHI_IDENTIFIER>
InChI=1S/C20H34O/c1-15-7-6-8-16(2)11-13-20(5)14-12-17(19(3,4)21)18(20)10-9-15/h7,11,17-18,21H,6,8-10,12-14H2,1-5H3/b15-7+,16-11+/t17-,18+,20+/m1/s1

> <INCHI_KEY>
OEBBSSBZPLXOHC-HJHANVIFSA-N

> <FORMULA>
C20H34O

> <MOLECULAR_WEIGHT>
290.491

> <EXACT_MASS>
290.260965715

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
55

> <JCHEM_AVERAGE_POLARIZABILITY>
35.7434258584493

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-[(1R,3aR,12aS)-3a,6,10-trimethyl-1H,2H,3H,3aH,4H,7H,8H,11H,12H,12aH-cyclopenta[11]annulen-1-yl]propan-2-ol

> <JCHEM_LOGP>
5.133508522666667

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
19.47748449613722

> <JCHEM_PKA_STRONGEST_BASIC>
-0.8403482813895805

> <JCHEM_POLAR_SURFACE_AREA>
20.23

> <JCHEM_REFRACTIVITY>
93.2366

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
2-[(1R,3aR,12aS)-3a,6,10-trimethyl-1H,2H,3H,4H,7H,8H,11H,12H,12aH-cyclopenta[11]annulen-1-yl]propan-2-ol

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 06-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-SEP-22         0                                  
HETATM    1  C   UNK     0       6.052  -7.369   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.267  -5.844   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.054  -4.896   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.626  -5.472   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.413  -4.523   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.039  -6.017   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.896  -4.790   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.173  -3.430   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.244  -2.323   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.977  -0.806   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.710   0.711   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.494  -0.539   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -0.540  -1.073   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       2.628  -2.998   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.161  -2.300   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.837  -0.917   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.362  -1.132   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       7.432  -0.024   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.629  -2.648   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       7.910  -3.743   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       7.695  -5.268   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   21                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6    7   14                                             
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   14                                                  
CONECT   10    9   11   12   13                                             
CONECT   11   10                                                            
CONECT   12   10                                                            
CONECT   13   10                                                            
CONECT   14    9    5   15                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20    2                                                       
MASTER        0    0    0    0    0    0    0    0   21    0   44    0
END

View in JSmol

Synonyms

Value	Source
(1R,3E,7E,11S,12R)-Dolabella-3,7-diene-18-ol	ChEBI

Chemical Formula

C₂₀H₃₄O

Average Mass

290.4910 Da

Monoisotopic Mass

290.26097 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

C\C1=C/C[C@@]2(C)CC[C@H]([C@@H]2CC\C(C)=C\CC1)C(C)(C)O

InChI Identifier

InChI=1S/C20H34O/c1-15-7-6-8-16(2)11-13-20(5)14-12-17(19(3,4)21)18(20)10-9-15/h7,11,17-18,21H,6,8-10,12-14H2,1-5H3/b15-7+,16-11+/t17-,18+,20+/m1/s1

InChI Key

OEBBSSBZPLXOHC-HJHANVIFSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Aglaia odorata	LOTUS Database	35616633
Dictyota dichotoma	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as dolabellane and neodolabellane diterpenoids. These are diterpenoids with a structure based on the dolabellane skeleton (3a,6,10-trimethyl-1-(propan-2-yl)-cyclopenta[11]annulene) or the neodolabellane skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Dolabellane and neodolabellane diterpenoids

Alternative Parents

Substituents

Dolabellane diterpenoid
Tertiary 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

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

64808239

KEGG Compound ID

Not Available

BioCyc ID

CPD-20109

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

57404370

PDB ID

Not Available

ChEBI ID

137565

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 2-[(1r,3ar,12as)-3a,6,10-trimethyl-1h,2h,3h,4h,7h,8h,11h,12h,12ah-cyclopenta[11]annulen-1-yl]propan-2-ol (NP0224296)

MOL for NP0224296 (2-[(1r,3ar,12as)-3a,6,10-trimethyl-1h,2h,3h,4h,7h,8h,11h,12h,12ah-cyclopenta[11]annulen-1-yl]propan-2-ol)

3D MOL for NP0224296 (2-[(1r,3ar,12as)-3a,6,10-trimethyl-1h,2h,3h,4h,7h,8h,11h,12h,12ah-cyclopenta[11]annulen-1-yl]propan-2-ol)

3D SDF for NP0224296 (2-[(1r,3ar,12as)-3a,6,10-trimethyl-1h,2h,3h,4h,7h,8h,11h,12h,12ah-cyclopenta[11]annulen-1-yl]propan-2-ol)

3D-SDF for NP0224296 (2-[(1r,3ar,12as)-3a,6,10-trimethyl-1h,2h,3h,4h,7h,8h,11h,12h,12ah-cyclopenta[11]annulen-1-yl]propan-2-ol)

PDB for NP0224296 (2-[(1r,3ar,12as)-3a,6,10-trimethyl-1h,2h,3h,4h,7h,8h,11h,12h,12ah-cyclopenta[11]annulen-1-yl]propan-2-ol)

3D PDB for NP0224296 (2-[(1r,3ar,12as)-3a,6,10-trimethyl-1h,2h,3h,4h,7h,8h,11h,12h,12ah-cyclopenta[11]annulen-1-yl]propan-2-ol)

SMILES for NP0224296 (2-[(1r,3ar,12as)-3a,6,10-trimethyl-1h,2h,3h,4h,7h,8h,11h,12h,12ah-cyclopenta[11]annulen-1-yl]propan-2-ol)

INCHI for NP0224296 (2-[(1r,3ar,12as)-3a,6,10-trimethyl-1h,2h,3h,4h,7h,8h,11h,12h,12ah-cyclopenta[11]annulen-1-yl]propan-2-ol)

Structure for NP0224296 (2-[(1r,3ar,12as)-3a,6,10-trimethyl-1h,2h,3h,4h,7h,8h,11h,12h,12ah-cyclopenta[11]annulen-1-yl]propan-2-ol)

3D Structure for NP0224296 (2-[(1r,3ar,12as)-3a,6,10-trimethyl-1h,2h,3h,4h,7h,8h,11h,12h,12ah-cyclopenta[11]annulen-1-yl]propan-2-ol)