NP-MRD: Showing NP-Card for 1,3-bis(acetyloxy)-7,8-dimethyl-7-(3-methylpenta-2,4-dien-1-yl)-1h,3h,5h,6h,6ah,8h,9h,10h-naphtho[1,8a-c]furan-5-yl 4-hydroxybenzoate (NP0201686)

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Record Information

Version

2.0

Created at

2022-09-04 20:46:31 UTC

Updated at

2022-09-04 20:46:31 UTC

NP-MRD ID

NP0201686

Secondary Accession Numbers

None

Natural Product Identification

Common Name

1,3-bis(acetyloxy)-7,8-dimethyl-7-(3-methylpenta-2,4-dien-1-yl)-1h,3h,5h,6h,6ah,8h,9h,10h-naphtho[1,8a-c]furan-5-yl 4-hydroxybenzoate

Description

AC1L1E0E belongs to the class of organic compounds known as colensane and clerodane diterpenoids. These are diterpenoids with a structure based on the clerodane or the colensane skeleton. Clerodanes arise from labdanes by two methyl migrations. 1,3-bis(acetyloxy)-7,8-dimethyl-7-(3-methylpenta-2,4-dien-1-yl)-1h,3h,5h,6h,6ah,8h,9h,10h-naphtho[1,8a-c]furan-5-yl 4-hydroxybenzoate is found in Casearia arborea. AC1L1E0E is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004241517542D          

 39 42  0  0  0  0            999 V2000
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  1  2  1  0  0  0  0
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 33 39  1  0  0  0  0
M  END

     RDKit          3D

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M  END


  Mrv1533004241517542D          

 39 42  0  0  0  0            999 V2000
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    5.0635   -1.2797    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0692   -0.4547    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7751   -1.6971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4924   -1.2895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2040   -1.7069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1984   -2.5319    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9100   -2.9493    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4811   -2.9395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7695   -2.5221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  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
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
  6 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
 12 17  1  0  0  0  0
  5 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
  5 21  1  0  0  0  0
 21 22  1  0  0  0  0
  2 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  1  0  0  0  0
 25 24  1  4  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 26 28  1  0  0  0  0
 28 29  2  0  0  0  0
 19 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  2  0  0  0  0
 31 33  1  0  0  0  0
 33 34  2  0  0  0  0
 34 35  1  0  0  0  0
 35 36  2  0  0  0  0
 36 37  1  0  0  0  0
 36 38  1  0  0  0  0
 38 39  2  0  0  0  0
 33 39  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0201686

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1CCC23C(OC(C)=O)OC(OC(C)=O)C2=CC(CC3C1(C)CC=C(C)C=C)OC(=O)C1=CC=C(O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C31H38O8/c1-7-18(2)12-14-30(6)19(3)13-15-31-25(28(36-20(4)32)39-29(31)37-21(5)33)16-24(17-26(30)31)38-27(35)22-8-10-23(34)11-9-22/h7-12,16,19,24,26,28-29,34H,1,13-15,17H2,2-6H3

> <INCHI_KEY>
RKOVIXOSRVSKPI-UHFFFAOYSA-N

> <FORMULA>
C31H38O8

> <MOLECULAR_WEIGHT>
538.637

> <EXACT_MASS>
538.256668184

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
77

> <JCHEM_AVERAGE_POLARIZABILITY>
58.474822328846514

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
1,3-bis(acetyloxy)-7,8-dimethyl-7-(3-methylpenta-2,4-dien-1-yl)-1H,3H,5H,6H,6aH,7H,8H,9H,10H-naphtho[4,4a-c]furan-5-yl 4-hydroxybenzoate

> <ALOGPS_LOGP>
5.16

> <JCHEM_LOGP>
5.793047602666665

> <ALOGPS_LOGS>
-5.58

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.493088297595648

> <JCHEM_PKA_STRONGEST_BASIC>
-4.548291848226022

> <JCHEM_POLAR_SURFACE_AREA>
108.36

> <JCHEM_REFRACTIVITY>
145.11619999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.41e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1,3-bis(acetyloxy)-7,8-dimethyl-7-(3-methylpenta-2,4-dien-1-yl)-1H,3H,5H,6H,6aH,8H,9H,10H-naphtho[4,4a-c]furan-5-yl 4-hydroxybenzoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-APR-15         0                                  
HETATM    1  C   UNK     0       0.111  -3.095   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.450  -2.334   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.461  -0.794   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.378  -0.143   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.128  -0.812   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.991   0.226   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       1.482  -0.084   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       0.459   1.068   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -1.049   0.758   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       0.945   2.529   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       3.627   1.629   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       5.157   1.457   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       6.195   2.594   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       5.729   4.062   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       4.225   4.393   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       6.768   5.200   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.467  -0.051   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.795  -0.831   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.785  -2.370   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.446  -3.131   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.117  -2.352   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       2.778  -3.113   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       2.046  -4.468   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       3.492  -4.478   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       2.667  -5.778   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       1.128  -5.714   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       0.415  -4.349   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       0.303  -7.014   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -1.235  -6.950   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       8.113  -3.150   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       9.452  -2.389   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       9.462  -0.849   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0      10.780  -3.168   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      12.119  -2.407   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      13.448  -3.186   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      13.437  -4.726   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0      14.765  -5.505   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0      12.098  -5.487   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      10.770  -4.708   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   22                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   17   21                                             
CONECT    6    5    7   11                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8                                                            
CONECT   11    6   12                                                       
CONECT   12   11   13   17                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14                                                            
CONECT   17   12    5   18                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20   30                                                  
CONECT   20   19   21                                                       
CONECT   21   20    5   22                                                  
CONECT   22   21    2   23   24                                             
CONECT   23   22                                                            
CONECT   24   22   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   29                                                       
CONECT   29   28                                                            
CONECT   30   19   31                                                       
CONECT   31   30   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31   34   39                                                  
CONECT   34   33   35                                                       
CONECT   35   34   36                                                       
CONECT   36   35   37   38                                                  
CONECT   37   36                                                            
CONECT   38   36   39                                                       
CONECT   39   38   33                                                       
MASTER        0    0    0    0    0    0    0    0   39    0   84    0
END

View in JSmol

Synonyms

Value	Source
1,3-Bis(acetyloxy)-7,8-dimethyl-7-(3-methylpenta-2,4-dien-1-yl)-1H,3H,5H,6H,6ah,7H,8H,9H,10H-naphtho[4,4a-c]furan-5-yl 4-hydroxybenzoic acid	Generator

Chemical Formula

C₃₁H₃₈O₈

Average Mass

538.6370 Da

Monoisotopic Mass

538.25667 Da

IUPAC Name

1,3-bis(acetyloxy)-7,8-dimethyl-7-(3-methylpenta-2,4-dien-1-yl)-1H,3H,5H,6H,6aH,7H,8H,9H,10H-naphtho[4,4a-c]furan-5-yl 4-hydroxybenzoate

Traditional Name

1,3-bis(acetyloxy)-7,8-dimethyl-7-(3-methylpenta-2,4-dien-1-yl)-1H,3H,5H,6H,6aH,8H,9H,10H-naphtho[4,4a-c]furan-5-yl 4-hydroxybenzoate

CAS Registry Number

Not Available

SMILES

CC1CCC23C(OC(C)=O)OC(OC(C)=O)C2=CC(CC3C1(C)CC=C(C)C=C)OC(=O)C1=CC=C(O)C=C1

InChI Identifier

InChI=1S/C31H38O8/c1-7-18(2)12-14-30(6)19(3)13-15-31-25(28(36-20(4)32)39-29(31)37-21(5)33)16-24(17-26(30)31)38-27(35)22-8-10-23(34)11-9-22/h7-12,16,19,24,26,28-29,34H,1,13-15,17H2,2-6H3

InChI Key

RKOVIXOSRVSKPI-UHFFFAOYSA-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
Casearia arborea	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as colensane and clerodane diterpenoids. These are diterpenoids with a structure based on the clerodane or the colensane skeleton. Clerodanes arise from labdanes by two methyl migrations.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Colensane and clerodane diterpenoids

Alternative Parents

Substituents

Clerodane diterpenoid
Naphthofuran
P-hydroxybenzoic acid alkyl ester
P-hydroxybenzoic acid ester
Benzoate ester
Benzoic acid or derivatives
Tricarboxylic acid or derivatives
Benzoyl
1-hydroxy-2-unsubstituted benzenoid
Phenol
Monocyclic benzene moiety
Benzenoid
Tetrahydrofuran
Carboxylic acid ester
Organoheterocyclic compound
Oxacycle
Acetal
Carboxylic acid derivative
Organic oxygen compound
Carbonyl group
Organooxygen compound
Hydrocarbon derivative
Organic oxide
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	5.16	ALOGPS
logP	5.79	ChemAxon
logS	-5.6	ALOGPS
pKa (Strongest Acidic)	8.49	ChemAxon
pKa (Strongest Basic)	-4.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	108.36 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	145.12 m³·mol⁻¹	ChemAxon
Polarizability	58.47 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	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

2586

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 1,3-bis(acetyloxy)-7,8-dimethyl-7-(3-methylpenta-2,4-dien-1-yl)-1h,3h,5h,6h,6ah,8h,9h,10h-naphtho[1,8a-c]furan-5-yl 4-hydroxybenzoate (NP0201686)

MOL for NP0201686 (1,3-bis(acetyloxy)-7,8-dimethyl-7-(3-methylpenta-2,4-dien-1-yl)-1h,3h,5h,6h,6ah,8h,9h,10h-naphtho[1,8a-c]furan-5-yl 4-hydroxybenzoate)

3D MOL for NP0201686 (1,3-bis(acetyloxy)-7,8-dimethyl-7-(3-methylpenta-2,4-dien-1-yl)-1h,3h,5h,6h,6ah,8h,9h,10h-naphtho[1,8a-c]furan-5-yl 4-hydroxybenzoate)

3D SDF for NP0201686 (1,3-bis(acetyloxy)-7,8-dimethyl-7-(3-methylpenta-2,4-dien-1-yl)-1h,3h,5h,6h,6ah,8h,9h,10h-naphtho[1,8a-c]furan-5-yl 4-hydroxybenzoate)

3D-SDF for NP0201686 (1,3-bis(acetyloxy)-7,8-dimethyl-7-(3-methylpenta-2,4-dien-1-yl)-1h,3h,5h,6h,6ah,8h,9h,10h-naphtho[1,8a-c]furan-5-yl 4-hydroxybenzoate)

PDB for NP0201686 (1,3-bis(acetyloxy)-7,8-dimethyl-7-(3-methylpenta-2,4-dien-1-yl)-1h,3h,5h,6h,6ah,8h,9h,10h-naphtho[1,8a-c]furan-5-yl 4-hydroxybenzoate)

3D PDB for NP0201686 (1,3-bis(acetyloxy)-7,8-dimethyl-7-(3-methylpenta-2,4-dien-1-yl)-1h,3h,5h,6h,6ah,8h,9h,10h-naphtho[1,8a-c]furan-5-yl 4-hydroxybenzoate)

SMILES for NP0201686 (1,3-bis(acetyloxy)-7,8-dimethyl-7-(3-methylpenta-2,4-dien-1-yl)-1h,3h,5h,6h,6ah,8h,9h,10h-naphtho[1,8a-c]furan-5-yl 4-hydroxybenzoate)

INCHI for NP0201686 (1,3-bis(acetyloxy)-7,8-dimethyl-7-(3-methylpenta-2,4-dien-1-yl)-1h,3h,5h,6h,6ah,8h,9h,10h-naphtho[1,8a-c]furan-5-yl 4-hydroxybenzoate)

Structure for NP0201686 (1,3-bis(acetyloxy)-7,8-dimethyl-7-(3-methylpenta-2,4-dien-1-yl)-1h,3h,5h,6h,6ah,8h,9h,10h-naphtho[1,8a-c]furan-5-yl 4-hydroxybenzoate)

3D Structure for NP0201686 (1,3-bis(acetyloxy)-7,8-dimethyl-7-(3-methylpenta-2,4-dien-1-yl)-1h,3h,5h,6h,6ah,8h,9h,10h-naphtho[1,8a-c]furan-5-yl 4-hydroxybenzoate)