NP-MRD: Showing NP-Card for (3s,4as,6ar,10ar,10bs)-3-ethenyl-3,4a,7,7,10a-pentamethyl-octahydro-1h-naphtho[2,1-b]pyran (NP0221392)

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Record Information

Version

2.0

Created at

2022-09-05 22:57:16 UTC

Updated at

2022-09-05 22:57:16 UTC

NP-MRD ID

NP0221392

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(3s,4as,6ar,10ar,10bs)-3-ethenyl-3,4a,7,7,10a-pentamethyl-octahydro-1h-naphtho[2,1-b]pyran

Description

ZINC34126010 belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units. (3s,4as,6ar,10ar,10bs)-3-ethenyl-3,4a,7,7,10a-pentamethyl-octahydro-1h-naphtho[2,1-b]pyran is found in Cistus creticus and Croton insularis. Based on a literature review very few articles have been published on ZINC34126010.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309062200572D          

 21 23  0  0  1  0            999 V2000
    4.5032    1.7553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6465    0.9428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0145    0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.6465   -0.1178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6020    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7770   -0.3020    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.1895   -1.0164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -1.0164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395   -1.0164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270   -0.3020    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3020   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4452   -1.1144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4733   -0.5841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1105    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395    0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9520    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6020   -0.3020    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  3  2  1  1  0  0  0
  3  4  1  6  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  7  6  1  6  0  0  0
  7  8  1  0  0  0  0
  8  9  1  6  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 12 11  1  6  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
 13 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
  7 19  1  0  0  0  0
 12 19  1  0  0  0  0
 19 20  1  6  0  0  0
  8 21  1  0  0  0  0
  3 21  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0221392

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1(C)CCC[C@]2(C)[C@@H]1CC[C@]1(C)O[C@@](C)(CC[C@@H]21)C=C

> <INCHI_IDENTIFIER>
InChI=1S/C20H34O/c1-7-18(4)13-9-16-19(5)12-8-11-17(2,3)15(19)10-14-20(16,6)21-18/h7,15-16H,1,8-14H2,2-6H3/t15-,16+,18-,19-,20+/m1/s1

> <INCHI_KEY>
IGGWKHQYMAJOHK-LHDHZVESSA-N

> <FORMULA>
C20H34O

> <MOLECULAR_WEIGHT>
290.491

> <EXACT_MASS>
290.260965715

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
55

> <JCHEM_AVERAGE_POLARIZABILITY>
36.09833959149877

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3S,4aS,6aR,10aR,10bS)-3-ethenyl-3,4a,7,7,10a-pentamethyl-dodecahydro-1H-naphtho[2,1-b]pyran

> <JCHEM_LOGP>
5.498561761333333

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.235396953661379

> <JCHEM_POLAR_SURFACE_AREA>
9.23

> <JCHEM_REFRACTIVITY>
89.47279999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(3S,4aS,6aR,10aR,10bS)-3-ethenyl-3,4a,7,7,10a-pentamethyl-octahydro-1H-naphtho[2,1-b]pyran

> <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       8.406   3.276   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.673   1.760   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.494   0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.673  -0.220   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.724   2.104   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.184   2.104   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.414   0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.184  -0.564   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.954  -1.897   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.414  -1.897   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.874  -1.897   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.104  -0.564   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.564  -0.564   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.831  -2.080   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.883  -1.090   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -0.206   0.770   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.564   2.104   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.104   2.104   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.874   0.770   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       3.644   2.104   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       6.724  -0.564   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5   21                                             
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8   19                                                  
CONECT    8    7    9   10   21                                             
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   19                                                  
CONECT   13   12   14   15   16                                             
CONECT   14   13                                                            
CONECT   15   13                                                            
CONECT   16   13   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18    7   12   20                                             
CONECT   20   19                                                            
CONECT   21    8    3                                                       
MASTER        0    0    0    0    0    0    0    0   21    0   46    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₀H₃₄O

Average Mass

290.4910 Da

Monoisotopic Mass

290.26097 Da

IUPAC Name

(3S,4aS,6aR,10aR,10bS)-3-ethenyl-3,4a,7,7,10a-pentamethyl-dodecahydro-1H-naphtho[2,1-b]pyran

Traditional Name

(3S,4aS,6aR,10aR,10bS)-3-ethenyl-3,4a,7,7,10a-pentamethyl-octahydro-1H-naphtho[2,1-b]pyran

CAS Registry Number

Not Available

SMILES

CC1(C)CCC[C@]2(C)[C@@H]1CC[C@]1(C)O[C@@](C)(CC[C@@H]21)C=C

InChI Identifier

InChI=1S/C20H34O/c1-7-18(4)13-9-16-19(5)12-8-11-17(2,3)15(19)10-14-20(16,6)21-18/h7,15-16H,1,8-14H2,2-6H3/t15-,16+,18-,19-,20+/m1/s1

InChI Key

IGGWKHQYMAJOHK-LHDHZVESSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Cistus creticus	LOTUS Database	35616633
Croton insularis	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Triterpenoids

Direct Parent

Triterpenoids

Alternative Parents

Substituents

Polycyclic triterpenoid
Triterpenoid
Naphthopyran
Naphthalene
Pyran
Oxane
Oxacycle
Organoheterocyclic compound
Ether
Dialkyl ether
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
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	5.5	ChemAxon
pKa (Strongest Basic)	-4.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	9.23 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	89.47 m³·mol⁻¹	ChemAxon
Polarizability	36.1 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	Yes	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

62623789

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

15560095

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (3s,4as,6ar,10ar,10bs)-3-ethenyl-3,4a,7,7,10a-pentamethyl-octahydro-1h-naphtho[2,1-b]pyran (NP0221392)

MOL for NP0221392 ((3s,4as,6ar,10ar,10bs)-3-ethenyl-3,4a,7,7,10a-pentamethyl-octahydro-1h-naphtho[2,1-b]pyran)

3D MOL for NP0221392 ((3s,4as,6ar,10ar,10bs)-3-ethenyl-3,4a,7,7,10a-pentamethyl-octahydro-1h-naphtho[2,1-b]pyran)

3D SDF for NP0221392 ((3s,4as,6ar,10ar,10bs)-3-ethenyl-3,4a,7,7,10a-pentamethyl-octahydro-1h-naphtho[2,1-b]pyran)

3D-SDF for NP0221392 ((3s,4as,6ar,10ar,10bs)-3-ethenyl-3,4a,7,7,10a-pentamethyl-octahydro-1h-naphtho[2,1-b]pyran)

PDB for NP0221392 ((3s,4as,6ar,10ar,10bs)-3-ethenyl-3,4a,7,7,10a-pentamethyl-octahydro-1h-naphtho[2,1-b]pyran)

3D PDB for NP0221392 ((3s,4as,6ar,10ar,10bs)-3-ethenyl-3,4a,7,7,10a-pentamethyl-octahydro-1h-naphtho[2,1-b]pyran)

SMILES for NP0221392 ((3s,4as,6ar,10ar,10bs)-3-ethenyl-3,4a,7,7,10a-pentamethyl-octahydro-1h-naphtho[2,1-b]pyran)

INCHI for NP0221392 ((3s,4as,6ar,10ar,10bs)-3-ethenyl-3,4a,7,7,10a-pentamethyl-octahydro-1h-naphtho[2,1-b]pyran)

Structure for NP0221392 ((3s,4as,6ar,10ar,10bs)-3-ethenyl-3,4a,7,7,10a-pentamethyl-octahydro-1h-naphtho[2,1-b]pyran)

3D Structure for NP0221392 ((3s,4as,6ar,10ar,10bs)-3-ethenyl-3,4a,7,7,10a-pentamethyl-octahydro-1h-naphtho[2,1-b]pyran)