NP-MRD: Showing NP-Card for (3r,4as,8ar)-3-ethenyl-1,1,3,6-tetramethyl-4a,7,8,8a-tetrahydro-4h-2-benzopyran (NP0178189)

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Record Information

Version

2.0

Created at

2022-09-03 16:08:16 UTC

Updated at

2022-09-03 16:08:17 UTC

NP-MRD ID

NP0178189

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(3r,4as,8ar)-3-ethenyl-1,1,3,6-tetramethyl-4a,7,8,8a-tetrahydro-4h-2-benzopyran

Description

Cabreuva oxide D belongs to the class of organic compounds known as benzopyrans. These are organic compounds containing a benzene ring fused to a pyran ring. Pyran a six-membered heterocyclic, non-aromatic ring, made up of five carbon atoms and one oxygen atom and containing two double bonds. Cabreuva oxide D is an extremely weak basic (essentially neutral) compound (based on its pKa). (3r,4as,8ar)-3-ethenyl-1,1,3,6-tetramethyl-4a,7,8,8a-tetrahydro-4h-2-benzopyran is found in Baccharis dracunculifolia and Myrocarpus fastigiatus. These are terpenes with three consecutive isoprene units.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 40 41  0  0  0  0  0  0  0  0999 V2000
   -1.4823   -2.7683   -0.7306 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2285   -1.5103   -1.0561 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5480   -0.4697   -0.0079 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.0293   -0.7211    0.3224 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7761   -0.7533    1.2179 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6218   -0.1189    1.2512 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5735   -1.1479    0.8575 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2621   -1.1151   -0.2443 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2450   -2.2131   -0.6149 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0895    0.0058   -1.1553 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7234    1.3152   -0.5108 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6810    1.1917    0.5646 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6905    1.6951    0.0859 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4973    2.8280   -0.9318 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4430    2.3522    1.2238 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3895    0.7377   -0.5833 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8972   -3.0734    0.2274 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2811   -3.5740   -1.4274 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8228   -1.2849   -2.0126 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5428   -0.9830   -0.6279 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1544   -1.5592    1.0160 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5087    0.1843    0.7124 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6464   -1.8663    1.2908 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3476   -0.5214    2.1665 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7945    0.0072    2.3766 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7009   -2.0034    1.5535 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8475   -3.2036   -0.3730 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1243   -2.0348    0.0471 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5852   -2.0858   -1.6490 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3441   -0.2663   -1.9418 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0525    0.1338   -1.7320 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4188    1.9657   -1.3566 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6787    1.7556   -0.1443 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9681    1.9492    1.3304 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4580    2.4321   -1.9724 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2968    3.5151   -0.6606 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4521    3.4366   -0.9226 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3503    1.8664    2.1810 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9887    3.3785    1.3569 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4733    2.5235    0.8733 H   0  0  0  0  0  0  0  0  0  0  0  0
  6  5  1  0
  5  3  1  0
  3  4  1  0
  3 16  1  0
 16 13  1  0
 13 14  1  0
 13 15  1  0
 13 12  1  0
 12 11  1  0
 11 10  1  0
 10  8  1  0
  8  9  1  0
  8  7  2  0
  3  2  1  6
  2  1  2  3
 12  6  1  0
  7  6  1  0
  6 25  1  1
  5 23  1  0
  5 24  1  0
  4 20  1  0
  4 21  1  0
  4 22  1  0
 14 35  1  0
 14 36  1  0
 14 37  1  0
 15 38  1  0
 15 39  1  0
 15 40  1  0
 12 34  1  1
 11 32  1  0
 11 33  1  0
 10 30  1  0
 10 31  1  0
  9 27  1  0
  9 28  1  0
  9 29  1  0
  7 26  1  0
  2 19  1  0
  1 17  1  0
  1 18  1  0
M  END


  Mrv0541 03071314322D          

 18 19  0  0  0  0            999 V2000
    4.9151    0.0762    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3276   -2.2820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3882   -2.2820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8545    0.3627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3848   -0.5558    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
    1.4289   -1.6500    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
    2.8579    0.0000    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
    2.1434   -0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  2  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
    3.5724   -0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    0.4125    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.0625    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  6  1  2  0  0  0  0
  8  7  1  0  0  0  0
 11  2  1  0  0  0  0
 11  7  1  0  0  0  0
 11  9  2  0  0  0  0
 12  9  1  0  0  0  0
 12 10  1  0  0  0  0
 13  8  1  0  0  0  0
 13 12  1  0  0  0  0
 14  3  1  0  0  0  0
 14  4  1  0  0  0  0
 14 13  1  0  0  0  0
 15  5  1  1  0  0  0
 15  6  1  6  0  0  0
 15 10  1  0  0  0  0
 16 14  1  0  0  0  0
 16 15  1  0  0  0  0
 12 17  1  1  0  0  0
 13 18  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0178189

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@@]12C[C@@](C)(OC(C)(C)[C@]1([H])CCC(C)=C2)C=C

> <INCHI_IDENTIFIER>
InChI=1S/C15H24O/c1-6-15(5)10-12-9-11(2)7-8-13(12)14(3,4)16-15/h6,9,12-13H,1,7-8,10H2,2-5H3/t12-,13-,15+/m1/s1

> <INCHI_KEY>
NIGRJVWIKNICMW-NFAWXSAZSA-N

> <FORMULA>
C15H24O

> <MOLECULAR_WEIGHT>
220.3505

> <EXACT_MASS>
220.18271539

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
26.454992339215423

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3R,4aS,8aR)-3-ethenyl-1,1,3,6-tetramethyl-3,4,4a,7,8,8a-hexahydro-1H-2-benzopyran

> <ALOGPS_LOGP>
4.34

> <JCHEM_LOGP>
3.702503786333333

> <ALOGPS_LOGS>
-4.57

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.2336200062683504

> <JCHEM_POLAR_SURFACE_AREA>
9.23

> <JCHEM_REFRACTIVITY>
69.50120000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.97e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3R,4aS,8aR)-3-ethenyl-1,1,3,6-tetramethyl-4a,7,8,8a-tetrahydro-4H-2-benzopyran

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 07-MAR-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-MAR-13         0                                  
HETATM    1  C   UNK     0       9.175   0.142   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.345  -4.260   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.325  -4.260   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.195   0.677   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.185  -1.037   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.001  -0.770   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       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       6.668  -2.310   0.000  0.00  0.00           O+0
HETATM   17  H   UNK     0       4.001   0.770   0.000  0.00  0.00           H+0
HETATM   18  H   UNK     0       4.001  -3.850   0.000  0.00  0.00           H+0
CONECT    1    6                                                            
CONECT    2   11                                                            
CONECT    3   14                                                            
CONECT    4   14                                                            
CONECT    5   15                                                            
CONECT    6    1   15                                                       
CONECT    7    8   11                                                       
CONECT    8    7   13                                                       
CONECT    9   11   12                                                       
CONECT   10   12   15                                                       
CONECT   11    2    7    9                                                  
CONECT   12    9   10   13   17                                             
CONECT   13    8   12   14   18                                             
CONECT   14    3    4   13   16                                             
CONECT   15    5    6   10   16                                             
CONECT   16   14   15                                                       
CONECT   17   12                                                            
CONECT   18   13                                                            
MASTER        0    0    0    0    0    0    0    0   18    0   38    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₅H₂₄O

Average Mass

220.3505 Da

Monoisotopic Mass

220.18272 Da

IUPAC Name

(3R,4aS,8aR)-3-ethenyl-1,1,3,6-tetramethyl-3,4,4a,7,8,8a-hexahydro-1H-2-benzopyran

Traditional Name

(3R,4aS,8aR)-3-ethenyl-1,1,3,6-tetramethyl-4a,7,8,8a-tetrahydro-4H-2-benzopyran

CAS Registry Number

Not Available

SMILES

[H][C@@]12C[C@@](C)(OC(C)(C)[C@]1([H])CCC(C)=C2)C=C

InChI Identifier

InChI=1S/C15H24O/c1-6-15(5)10-12-9-11(2)7-8-13(12)14(3,4)16-15/h6,9,12-13H,1,7-8,10H2,2-5H3/t12-,13-,15+/m1/s1

InChI Key

NIGRJVWIKNICMW-NFAWXSAZSA-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
Baccharis dracunculifolia	LOTUS Database	35616633
Myrocarpus fastigiatus	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as benzopyrans. These are organic compounds containing a benzene ring fused to a pyran ring. Pyran a six-membered heterocyclic, non-aromatic ring, made up of five carbon atoms and one oxygen atom and containing two double bonds.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzopyrans

Sub Class

Not Available

Direct Parent

Benzopyrans

Alternative Parents

Substituents

Benzopyran
Oxane
Oxacycle
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	4.34	ALOGPS
logP	3.7	ChemAxon
logS	-4.6	ALOGPS
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	69.5 m³·mol⁻¹	ChemAxon
Polarizability	26.45 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0059836

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

21603104

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (3r,4as,8ar)-3-ethenyl-1,1,3,6-tetramethyl-4a,7,8,8a-tetrahydro-4h-2-benzopyran (NP0178189)

MOL for NP0178189 ((3r,4as,8ar)-3-ethenyl-1,1,3,6-tetramethyl-4a,7,8,8a-tetrahydro-4h-2-benzopyran)

3D MOL for NP0178189 ((3r,4as,8ar)-3-ethenyl-1,1,3,6-tetramethyl-4a,7,8,8a-tetrahydro-4h-2-benzopyran)

3D SDF for NP0178189 ((3r,4as,8ar)-3-ethenyl-1,1,3,6-tetramethyl-4a,7,8,8a-tetrahydro-4h-2-benzopyran)

3D-SDF for NP0178189 ((3r,4as,8ar)-3-ethenyl-1,1,3,6-tetramethyl-4a,7,8,8a-tetrahydro-4h-2-benzopyran)

PDB for NP0178189 ((3r,4as,8ar)-3-ethenyl-1,1,3,6-tetramethyl-4a,7,8,8a-tetrahydro-4h-2-benzopyran)

3D PDB for NP0178189 ((3r,4as,8ar)-3-ethenyl-1,1,3,6-tetramethyl-4a,7,8,8a-tetrahydro-4h-2-benzopyran)

SMILES for NP0178189 ((3r,4as,8ar)-3-ethenyl-1,1,3,6-tetramethyl-4a,7,8,8a-tetrahydro-4h-2-benzopyran)

INCHI for NP0178189 ((3r,4as,8ar)-3-ethenyl-1,1,3,6-tetramethyl-4a,7,8,8a-tetrahydro-4h-2-benzopyran)

Structure for NP0178189 ((3r,4as,8ar)-3-ethenyl-1,1,3,6-tetramethyl-4a,7,8,8a-tetrahydro-4h-2-benzopyran)

3D Structure for NP0178189 ((3r,4as,8ar)-3-ethenyl-1,1,3,6-tetramethyl-4a,7,8,8a-tetrahydro-4h-2-benzopyran)