NP-MRD: Showing NP-Card for (1r,13r,16s,18r)-3-hydroxy-13,17,17-trimethyl-8,12-dioxapentacyclo[11.4.1.0²,¹¹.0⁴,⁹.0¹⁶,¹⁸]octadeca-2(11),3,5,9-tetraen-7-one (NP0226279)

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Record Information

Version

2.0

Created at

2022-09-06 05:15:48 UTC

Updated at

2022-09-06 05:15:48 UTC

NP-MRD ID

NP0226279

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r,13r,16s,18r)-3-hydroxy-13,17,17-trimethyl-8,12-dioxapentacyclo[11.4.1.0²,¹¹.0⁴,⁹.0¹⁶,¹⁸]octadeca-2(11),3,5,9-tetraen-7-one

Description

Eriobrucinol belongs to the class of organic compounds known as linear pyranocoumarins. These are organic compounds containing a pyran (or a hydrogenated derivative) linearly fused to a coumarin moiety. (1r,13r,16s,18r)-3-hydroxy-13,17,17-trimethyl-8,12-dioxapentacyclo[11.4.1.0²,¹¹.0⁴,⁹.0¹⁶,¹⁸]octadeca-2(11),3,5,9-tetraen-7-one is found in Philotheca brucei. (1r,13r,16s,18r)-3-hydroxy-13,17,17-trimethyl-8,12-dioxapentacyclo[11.4.1.0²,¹¹.0⁴,⁹.0¹⁶,¹⁸]octadeca-2(11),3,5,9-tetraen-7-one was first documented in 2013 (PMID: 23730958). Based on a literature review very few articles have been published on Eriobrucinol (PMID: 31849214).

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309062207152D          

 23 27  0  0  1  0            999 V2000
   -0.4456   -1.3924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1392   -0.8105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7092   -1.4069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4757   -0.2170    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1077    0.3550    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7880    1.1347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0610    1.0900    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1062    1.8979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8213    1.4674    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5396    1.0309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2706    1.4132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9673    0.9712    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6983    1.3535    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3950    0.9116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1260    1.2939    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3605    0.0873    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6294   -0.2950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9328    0.1470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2017   -0.2354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1673   -1.0596    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5051    0.2066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7670   -0.2343    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1511    0.2836    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  1  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  6  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  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
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 12 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 19 21  1  0  0  0  0
 10 21  2  0  0  0  0
 22 21  1  1  0  0  0
  2 22  1  0  0  0  0
 23 22  1  1  0  0  0
  4 23  1  0  0  0  0
  7 23  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0226279

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1(C)[C@H]2CC[C@@]3(C)OC4=C([C@@H]1[C@@H]23)C(O)=C1C=CC(=O)OC1=C4

> <INCHI_IDENTIFIER>
InChI=1S/C19H20O4/c1-18(2)10-6-7-19(3)15(10)16(18)14-12(23-19)8-11-9(17(14)21)4-5-13(20)22-11/h4-5,8,10,15-16,21H,6-7H2,1-3H3/t10-,15+,16+,19+/m0/s1

> <INCHI_KEY>
FIAJUSACIWBXJG-NIOWNGSVSA-N

> <FORMULA>
C19H20O4

> <MOLECULAR_WEIGHT>
312.365

> <EXACT_MASS>
312.136159124

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
43

> <JCHEM_AVERAGE_POLARIZABILITY>
33.24795504826764

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,13R,16S,18R)-3-hydroxy-13,17,17-trimethyl-8,12-dioxapentacyclo[11.4.1.0^{2,11}.0^{4,9}.0^{16,18}]octadeca-2(11),3,5,9-tetraen-7-one

> <JCHEM_LOGP>
3.1803110523333338

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.007352250320725

> <JCHEM_PKA_STRONGEST_BASIC>
-4.887975916893701

> <JCHEM_POLAR_SURFACE_AREA>
55.760000000000005

> <JCHEM_REFRACTIVITY>
85.8714

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1R,13R,16S,18R)-3-hydroxy-13,17,17-trimethyl-8,12-dioxapentacyclo[11.4.1.0^{2,11}.0^{4,9}.0^{16,18}]octadeca-2(11),3,5,9-tetraen-7-one

> <JCHEM_VEBER_RULE>
0

$$$$

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      -0.832  -2.599   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.260  -1.513   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.324  -2.626   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.888  -0.405   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.068   0.663   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.471   2.118   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.114   2.035   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.198   3.543   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       1.533   2.739   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       2.874   1.924   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.239   2.638   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.539   1.813   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       6.904   2.527   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       8.204   1.702   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       9.569   2.415   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       8.140   0.163   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.775  -0.551   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.475   0.274   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.110  -0.439   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       4.046  -1.978   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       2.810   0.386   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       1.432  -0.437   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       0.282   0.529   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4   22                                             
CONECT    3    2                                                            
CONECT    4    2    5   23                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8    9   23                                             
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9   11   21                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   18                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   12   19                                                  
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   10   22                                                  
CONECT   22   21    2   23                                                  
CONECT   23   22    4    7                                                  
MASTER        0    0    0    0    0    0    0    0   23    0   54    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₉H₂₀O₄

Average Mass

312.3650 Da

Monoisotopic Mass

312.13616 Da

IUPAC Name

(1R,13R,16S,18R)-3-hydroxy-13,17,17-trimethyl-8,12-dioxapentacyclo[11.4.1.0^{2,11}.0^{4,9}.0^{16,18}]octadeca-2(11),3,5,9-tetraen-7-one

Traditional Name

(1R,13R,16S,18R)-3-hydroxy-13,17,17-trimethyl-8,12-dioxapentacyclo[11.4.1.0^{2,11}.0^{4,9}.0^{16,18}]octadeca-2(11),3,5,9-tetraen-7-one

CAS Registry Number

Not Available

SMILES

CC1(C)[C@H]2CC[C@@]3(C)OC4=C([C@@H]1[C@@H]23)C(O)=C1C=CC(=O)OC1=C4

InChI Identifier

InChI=1S/C19H20O4/c1-18(2)10-6-7-19(3)15(10)16(18)14-12(23-19)8-11-9(17(14)21)4-5-13(20)22-11/h4-5,8,10,15-16,21H,6-7H2,1-3H3/t10-,15+,16+,19+/m0/s1

InChI Key

FIAJUSACIWBXJG-NIOWNGSVSA-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
Eriostemon brucei	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as linear pyranocoumarins. These are organic compounds containing a pyran (or a hydrogenated derivative) linearly fused to a coumarin moiety.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Coumarins and derivatives

Sub Class

Pyranocoumarins

Direct Parent

Linear pyranocoumarins

Alternative Parents

Substituents

Linear pyranocoumarin
Pyranochromene
Chromane
Benzopyran
1-benzopyran
1-hydroxy-4-unsubstituted benzenoid
Alkyl aryl ether
Phenol
Pyranone
Benzenoid
Pyran
Heteroaromatic compound
Lactone
Oxacycle
Ether
Organoheterocyclic compound
Organooxygen compound
Organic oxygen 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	3.18	ChemAxon
pKa (Strongest Acidic)	8.01	ChemAxon
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	55.76 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	85.87 m³·mol⁻¹	ChemAxon
Polarizability	33.25 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	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

C00019900

Chemspider ID

74176500

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

102059837

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Day AJ, Sumby CJ, George JH: Biomimetic Synthetic Studies on the Bruceol Family of Meroterpenoid Natural Products. J Org Chem. 2020 Feb 21;85(4):2103-2117. doi: 10.1021/acs.joc.9b02862. Epub 2020 Jan 6. [PubMed:31849214 ]
Yeom HS, Li H, Tang Y, Hsung RP: Total syntheses of cannabicyclol, clusiacyclol A and B, iso-eriobrucinol A and B, and eriobrucinol. Org Lett. 2013 Jun 21;15(12):3130-3. doi: 10.1021/ol401335u. Epub 2013 Jun 3. [PubMed:23730958 ]
LOTUS database [Link]

Showing NP-Card for (1r,13r,16s,18r)-3-hydroxy-13,17,17-trimethyl-8,12-dioxapentacyclo[11.4.1.0²,¹¹.0⁴,⁹.0¹⁶,¹⁸]octadeca-2(11),3,5,9-tetraen-7-one (NP0226279)

MOL for NP0226279 ((1r,13r,16s,18r)-3-hydroxy-13,17,17-trimethyl-8,12-dioxapentacyclo[11.4.1.0²,¹¹.0⁴,⁹.0¹⁶,¹⁸]octadeca-2(11),3,5,9-tetraen-7-one)

3D MOL for NP0226279 ((1r,13r,16s,18r)-3-hydroxy-13,17,17-trimethyl-8,12-dioxapentacyclo[11.4.1.0²,¹¹.0⁴,⁹.0¹⁶,¹⁸]octadeca-2(11),3,5,9-tetraen-7-one)

3D SDF for NP0226279 ((1r,13r,16s,18r)-3-hydroxy-13,17,17-trimethyl-8,12-dioxapentacyclo[11.4.1.0²,¹¹.0⁴,⁹.0¹⁶,¹⁸]octadeca-2(11),3,5,9-tetraen-7-one)

3D-SDF for NP0226279 ((1r,13r,16s,18r)-3-hydroxy-13,17,17-trimethyl-8,12-dioxapentacyclo[11.4.1.0²,¹¹.0⁴,⁹.0¹⁶,¹⁸]octadeca-2(11),3,5,9-tetraen-7-one)

PDB for NP0226279 ((1r,13r,16s,18r)-3-hydroxy-13,17,17-trimethyl-8,12-dioxapentacyclo[11.4.1.0²,¹¹.0⁴,⁹.0¹⁶,¹⁸]octadeca-2(11),3,5,9-tetraen-7-one)

3D PDB for NP0226279 ((1r,13r,16s,18r)-3-hydroxy-13,17,17-trimethyl-8,12-dioxapentacyclo[11.4.1.0²,¹¹.0⁴,⁹.0¹⁶,¹⁸]octadeca-2(11),3,5,9-tetraen-7-one)

SMILES for NP0226279 ((1r,13r,16s,18r)-3-hydroxy-13,17,17-trimethyl-8,12-dioxapentacyclo[11.4.1.0²,¹¹.0⁴,⁹.0¹⁶,¹⁸]octadeca-2(11),3,5,9-tetraen-7-one)

INCHI for NP0226279 ((1r,13r,16s,18r)-3-hydroxy-13,17,17-trimethyl-8,12-dioxapentacyclo[11.4.1.0²,¹¹.0⁴,⁹.0¹⁶,¹⁸]octadeca-2(11),3,5,9-tetraen-7-one)

Structure for NP0226279 ((1r,13r,16s,18r)-3-hydroxy-13,17,17-trimethyl-8,12-dioxapentacyclo[11.4.1.0²,¹¹.0⁴,⁹.0¹⁶,¹⁸]octadeca-2(11),3,5,9-tetraen-7-one)

3D Structure for NP0226279 ((1r,13r,16s,18r)-3-hydroxy-13,17,17-trimethyl-8,12-dioxapentacyclo[11.4.1.0²,¹¹.0⁴,⁹.0¹⁶,¹⁸]octadeca-2(11),3,5,9-tetraen-7-one)