NP-MRD: Showing NP-Card for 1-Acetoxydihydroisochromolaenin (NP0061880)

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Record Information

Version

2.0

Created at

2022-04-28 06:34:44 UTC

Updated at

2022-04-28 06:34:44 UTC

NP-MRD ID

NP0061880

Secondary Accession Numbers

None

Natural Product Identification

Common Name

1-Acetoxydihydroisochromolaenin

Description

(5R,5aR,6S)-1,5-dimethyl-8-methylidene-4H,5H,5aH,6H,7H,8H-naphtho[2,1-b]furan-6-yl acetate belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. 1-Acetoxydihydroisochromolaenin is found in Chromolaena spp. Based on a literature review very few articles have been published on (5R,5aR,6S)-1,5-dimethyl-8-methylidene-4H,5H,5aH,6H,7H,8H-naphtho[2,1-b]furan-6-yl acetate.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 40 42  0  0  0  0  0  0  0  0999 V2000
    0.0053   -3.2972   -1.6661 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0902   -2.0563   -1.2312 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1095   -1.3590   -0.7927 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9884   -0.3435    0.0160 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1957    0.3430    0.4451 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5250   -0.0615    0.6036 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0395   -1.4089    0.3482 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1663    1.0924    1.0421 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2954    2.0712    1.1299 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1123    1.6680    0.7841 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8441    2.3870    0.7222 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3306    1.6400    0.2331 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5057    1.9275   -1.2421 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3007    0.1674    0.5355 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4863   -0.5959    0.1373 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.6843    0.1484    0.0918 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8001   -0.1070    0.8416 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0481    0.7309    0.7419 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7514   -1.0898    1.6389 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3981   -1.3402   -1.1745 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9369   -3.8009   -1.7044 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8910   -3.8050   -1.9890 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0590   -1.7004   -1.1503 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9873   -1.4940    0.9628 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3961   -1.5788   -0.6918 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4060   -2.2298    0.7409 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2152    1.1709    1.2737 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9719    3.3672    0.1660 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6390    2.7451    1.7782 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2606    2.0412    0.7303 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3102    3.0208   -1.3746 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2826    1.4090   -1.8253 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5175    1.7422   -1.6079 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2063    0.1082    1.6626 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6818   -1.4039    0.9061 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5505    0.6510    1.7219 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8288    1.7571    0.4264 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7389    0.2432    0.0078 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2426   -2.0744   -1.1887 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5517   -0.6854   -2.0496 H   0  0  0  0  0  0  0  0  0  0  0  0
 13 12  1  0
 12 11  1  0
 11 10  1  0
 10  5  2  0
  5  6  1  0
  6  7  1  0
  6  8  2  0
  8  9  1  0
  5  4  1  0
  4  3  2  0
  3  2  1  0
  2  1  2  3
  2 20  1  0
 20 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 17 19  2  0
 15 14  1  0
 14 12  1  0
  9 10  1  0
 14  4  1  0
 13 31  1  0
 13 32  1  0
 13 33  1  0
 12 30  1  1
 11 28  1  0
 11 29  1  0
  7 24  1  0
  7 25  1  0
  7 26  1  0
  8 27  1  0
  3 23  1  0
  1 21  1  0
  1 22  1  0
 20 39  1  0
 20 40  1  0
 15 35  1  1
 18 36  1  0
 18 37  1  0
 18 38  1  0
 14 34  1  1
M  END


  Mrv1652304282208342D          

 20 22  0  0  1  0            999 V2000
    2.8571    0.8217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2917    0.1205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2470    1.5487    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8124    2.2499    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9878    2.2242    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5978    1.4972    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0325    0.7959    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7732    1.4714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3386    2.1727    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7286    2.8997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5532    2.9254    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9432    3.6524    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4626    1.9760    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5232    1.1532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2406    0.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4373    0.0402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2024    2.9770    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0270    3.0027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4170    3.7297    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4616    2.3015    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  1  0  0  0
  6  7  2  0  0  0  0
  1  7  1  0  0  0  0
  6  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
  5 11  1  0  0  0  0
 11 12  1  1  0  0  0
  9 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
  8 15  1  0  0  0  0
 15 16  1  0  0  0  0
  4 17  1  1  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0061880

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H]1CC2=C(C(C)=CO2)C2=CC(=C)C[C@H](OC(C)=O)[C@H]12

> <INCHI_IDENTIFIER>
InChI=1S/C17H20O3/c1-9-5-13-16(15(6-9)20-12(4)18)10(2)7-14-17(13)11(3)8-19-14/h5,8,10,15-16H,1,6-7H2,2-4H3/t10-,15+,16-/m1/s1

> <INCHI_KEY>
XDFMDORPDZXRFS-HPEXNQPKSA-N

> <FORMULA>
C17H20O3

> <MOLECULAR_WEIGHT>
272.344

> <EXACT_MASS>
272.141244504

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
40

> <JCHEM_AVERAGE_POLARIZABILITY>
30.42357566469511

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(5R,5aR,6S)-1,5-dimethyl-8-methylidene-4H,5H,5aH,6H,7H,8H-naphtho[2,1-b]furan-6-yl acetate

> <ALOGPS_LOGP>
3.75

> <JCHEM_LOGP>
2.9346170623333343

> <ALOGPS_LOGS>
-3.89

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-2.691210725938276

> <JCHEM_POLAR_SURFACE_AREA>
39.44

> <JCHEM_REFRACTIVITY>
78.092

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.54e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(5R,5aR,6S)-1,5-dimethyl-8-methylidene-4H,5H,5aH,6H,7H-naphtho[2,1-b]furan-6-yl acetate

> <JCHEM_VEBER_RULE>
1

$$$$

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       5.333   1.534   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.144   0.225   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.061   2.891   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.250   4.200   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.711   4.152   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.983   2.795   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.794   1.486   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.443   2.747   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.632   4.056   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.360   5.413   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.899   5.461   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.627   6.818   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -0.863   3.689   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      -0.977   2.153   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.449   1.571   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.816   0.075   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       5.978   5.557   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       7.517   5.605   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       8.245   6.962   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       8.328   4.296   0.000  0.00  0.00           C+0
CONECT    1    2    3    7                                                  
CONECT    2    1                                                            
CONECT    3    1    4                                                       
CONECT    4    3    5   17                                                  
CONECT    5    4    6   11                                                  
CONECT    6    5    7    8                                                  
CONECT    7    6    1                                                       
CONECT    8    6    9   15                                                  
CONECT    9    8   10   13                                                  
CONECT   10    9   11                                                       
CONECT   11   10    5   12                                                  
CONECT   12   11                                                            
CONECT   13    9   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14    8   16                                                  
CONECT   16   15                                                            
CONECT   17    4   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   44    0
END

View in JSmol

Synonyms

Value	Source
(5R,5AR,6S)-1,5-dimethyl-8-methylidene-4H,5H,5ah,6H,7H,8H-naphtho[2,1-b]furan-6-yl acetic acid	Generator

Chemical Formula

C₁₇H₂₀O₃

Average Mass

272.3440 Da

Monoisotopic Mass

272.14124 Da

IUPAC Name

(5R,5aR,6S)-1,5-dimethyl-8-methylidene-4H,5H,5aH,6H,7H,8H-naphtho[2,1-b]furan-6-yl acetate

Traditional Name

(5R,5aR,6S)-1,5-dimethyl-8-methylidene-4H,5H,5aH,6H,7H-naphtho[2,1-b]furan-6-yl acetate

CAS Registry Number

Not Available

SMILES

C[C@@H]1CC2=C(C(C)=CO2)C2=CC(=C)C[C@H](OC(C)=O)[C@H]12

InChI Identifier

InChI=1S/C17H20O3/c1-9-5-13-16(15(6-9)20-12(4)18)10(2)7-14-17(13)11(3)8-19-14/h5,8,10,15-16H,1,6-7H2,2-4H3/t10-,15+,16-/m1/s1

InChI Key

XDFMDORPDZXRFS-HPEXNQPKSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Chromolaena spp.	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

Cadinane sesquiterpenoid
Sesquiterpenoid
Naphthofuran
Benzofuran
Furan
Heteroaromatic compound
Carboxylic acid ester
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Oxacycle
Organoheterocyclic compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Carbonyl group
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic 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	3.75	ALOGPS
logP	2.93	ChemAxon
logS	-3.9	ALOGPS
pKa (Strongest Basic)	-2.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	39.44 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	78.09 m³·mol⁻¹	ChemAxon
Polarizability	30.42 Å³	ChemAxon
Number of Rings	3	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

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

162874917

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for 1-Acetoxydihydroisochromolaenin (NP0061880)

MOL for NP0061880 (1-Acetoxydihydroisochromolaenin)

3D MOL for NP0061880 (1-Acetoxydihydroisochromolaenin)

3D SDF for NP0061880 (1-Acetoxydihydroisochromolaenin)

3D-SDF for NP0061880 (1-Acetoxydihydroisochromolaenin)

PDB for NP0061880 (1-Acetoxydihydroisochromolaenin)

3D PDB for NP0061880 (1-Acetoxydihydroisochromolaenin)

SMILES for NP0061880 (1-Acetoxydihydroisochromolaenin)

INCHI for NP0061880 (1-Acetoxydihydroisochromolaenin)

Structure for NP0061880 (1-Acetoxydihydroisochromolaenin)

3D Structure for NP0061880 (1-Acetoxydihydroisochromolaenin)