NP-MRD: Showing NP-Card for Decursinol (NP0051442)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-04-27 22:48:28 UTC

Updated at

2022-04-27 22:48:28 UTC

NP-MRD ID

NP0051442

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Decursinol

Description

Decursinol 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. Decursinol is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Decursinol is found in Aegle marmelos , Angelica decursiva , Angelica gigas , Phlojodicarpus villosus, Seseli grandivittatum, Seseli tortuosum LBS.Eur. and Smyrniopsis aucheri. Decursinol was first documented in 2021 (PMID: 34681611). Based on a literature review a small amount of articles have been published on decursinol (PMID: 35163846) (PMID: 33921050) (PMID: 33648943) (PMID: 33148043).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 32 34  0  0  0  0  0  0  0  0999 V2000
   -3.4747    0.9867    1.0973 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3236    0.6395    0.1447 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.6150    1.3959   -1.1597 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1267    1.2140    0.6379 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1058    0.6195    0.4008 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2473    1.3640    0.1799 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4263    0.6887   -0.0467 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5097    1.4103   -0.2565 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6819    0.8951   -0.4820 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6674    1.6285   -0.6728 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8111   -0.4769   -0.5055 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7151   -1.2864   -0.2932 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4964   -0.7058   -0.0588 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3403   -1.4246    0.1649 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1698   -0.7584    0.3900 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0947   -1.4982    0.6347 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2509   -0.8299   -0.0799 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.2046   -1.1516   -1.4557 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0337    1.3873    2.0472 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2059    1.6566    0.6435 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9698    0.0350    1.3881 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6431    1.2189   -1.4987 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5564    2.4816   -0.8803 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8436    1.2178   -1.9120 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1920    2.4427    0.1897 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7840   -0.9065   -0.6926 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8071   -2.3579   -0.3098 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4090   -2.5202    0.1528 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3086   -1.4096    1.7240 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0586   -2.5472    0.3406 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1785   -1.3071    0.2986 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4748   -2.1022   -1.5250 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5 15  2  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 15 14  1  0
 14 13  2  0
 13 12  1  0
 12 11  2  0
 11  9  1  0
  9 10  2  0
  9  8  1  0
  8  7  1  0
  7  6  2  0
 17  2  1  0
  7 13  1  0
  6  5  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  3 22  1  0
  3 23  1  0
  3 24  1  0
 16 29  1  0
 16 30  1  0
 17 31  1  1
 18 32  1  0
 14 28  1  0
 12 27  1  0
 11 26  1  0
  6 25  1  0
M  END


  Mrv1652304282200482D          

 18 20  0  0  1  0            999 V2000
    2.8579   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    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
    2.1434   -0.4125    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
    0.0000   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 O   0  0  0  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
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.0000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7240    1.5246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1113    0.8538    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  1  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
  4 11  1  0  0  0  0
  2 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
  1 15  1  0  0  0  0
 14 16  1  1  0  0  0
 13 17  1  0  0  0  0
 13 18  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0051442

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1(C)OC2=C(C[C@@H]1O)C=C1C=CC(=O)OC1=C2

> <INCHI_IDENTIFIER>
InChI=1S/C14H14O4/c1-14(2)12(15)6-9-5-8-3-4-13(16)17-10(8)7-11(9)18-14/h3-5,7,12,15H,6H2,1-2H3/t12-/m0/s1

> <INCHI_KEY>
BGXFQDFSVDZUIW-LBPRGKRZSA-N

> <FORMULA>
C14H14O4

> <MOLECULAR_WEIGHT>
246.262

> <EXACT_MASS>
246.089208931

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
32

> <JCHEM_AVERAGE_POLARIZABILITY>
25.442755470326574

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(12S)-12-hydroxy-13,13-dimethyl-4,14-dioxatricyclo[8.4.0.0^{3,8}]tetradeca-1(10),2,6,8-tetraen-5-one

> <ALOGPS_LOGP>
2.11

> <JCHEM_LOGP>
1.7323936069999994

> <ALOGPS_LOGS>
-2.68

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.82481629989488

> <JCHEM_PKA_STRONGEST_BASIC>
-3.312825350425978

> <JCHEM_POLAR_SURFACE_AREA>
55.760000000000005

> <JCHEM_REFRACTIVITY>
66.3409

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.12e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(12S)-12-hydroxy-13,13-dimethyl-4,14-dioxatricyclo[8.4.0.0^{3,8}]tetradeca-1(10),2,6,8-tetraen-5-one

> <JCHEM_VEBER_RULE>
0

$$$$

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       5.335  -0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      -1.334   2.310   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       1.334   2.310   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       6.668   2.310   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.002   0.000   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       9.336  -0.770   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       8.818   2.846   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       9.541   1.594   0.000  0.00  0.00           C+0
CONECT    1    2    6   15                                                  
CONECT    2    1    3   12                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   11                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5    1                                                       
CONECT    7    5    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9    4                                                       
CONECT   12    2   13                                                       
CONECT   13   12   14   17   18                                             
CONECT   14   13   15   16                                                  
CONECT   15   14    1                                                       
CONECT   16   14                                                            
CONECT   17   13                                                            
CONECT   18   13                                                            
MASTER        0    0    0    0    0    0    0    0   18    0   40    0
END

View in JSmol

Synonyms

Value	Source
(+)-Decursinol	ChEBI
(S)-(+)-Decursinol	ChEBI
Decursin	MeSH
Decursinol angelate	MeSH

Chemical Formula

C₁₄H₁₄O₄

Average Mass

246.2620 Da

Monoisotopic Mass

246.08921 Da

IUPAC Name

(12S)-12-hydroxy-13,13-dimethyl-4,14-dioxatricyclo[8.4.0.0^{3,8}]tetradeca-1(10),2,6,8-tetraen-5-one

Traditional Name

(12S)-12-hydroxy-13,13-dimethyl-4,14-dioxatricyclo[8.4.0.0^{3,8}]tetradeca-1(10),2,6,8-tetraen-5-one

CAS Registry Number

Not Available

SMILES

CC1(C)OC2=C(C[C@@H]1O)C=C1C=CC(=O)OC1=C2

InChI Identifier

InChI=1S/C14H14O4/c1-14(2)12(15)6-9-5-8-3-4-13(16)17-10(8)7-11(9)18-14/h3-5,7,12,15H,6H2,1-2H3/t12-/m0/s1

InChI Key

BGXFQDFSVDZUIW-LBPRGKRZSA-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
Aegle marmelos	Plant	KNApSAcK
Angelica decursiva	Plant	KNApSAcK
Angelica gigas	Plant	KNApSAcK
Phlojodicarpus villosus	LOTUS Database	35616633
Seseli grandivittatum	Plant	KNApSAcK
Seseli tortuosum LBS.Eur.	Plant	KNApSAcK
Smyrniopsis aucheri	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
2,2-dimethyl-1-benzopyran
Chromane
Benzopyran
1-benzopyran
Alkyl aryl ether
Pyranone
Benzenoid
Pyran
Heteroaromatic compound
Lactone
Secondary alcohol
Ether
Oxacycle
Organoheterocyclic compound
Alcohol
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

organic heterotricyclic compound (CHEBI:4354 )
secondary alcohol (CHEBI:4354 )
delta-lactone (CHEBI:4354 )
cyclic ether (CHEBI:4354 )

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	2.11	ALOGPS
logP	1.73	ChemAxon
logS	-2.7	ALOGPS
pKa (Strongest Acidic)	13.82	ChemAxon
pKa (Strongest Basic)	-3.3	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	66.34 m³·mol⁻¹	ChemAxon
Polarizability	25.44 Å³	ChemAxon
Number of Rings	3	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

C00002466

Chemspider ID

390649

KEGG Compound ID

C09259

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

442127

PDB ID

Not Available

ChEBI ID

4354

Good Scents ID

rw1725521

References

General References

Chang SN, Khan I, Kim CG, Park SM, Choi DK, Lee H, Hwang BS, Kang SC, Park JG: Correction: Chang et al. Decursinol Angelate Arrest Melanoma Cell Proliferation by Initiating Cell Death and Tumor Shrinkage via Induction of Apoptosis. Int. J. Mol. Sci. 2021, 22, 4096. Int J Mol Sci. 2022 Jan 31;23(3). pii: ijms23031629. doi: 10.3390/ijms23031629. [PubMed:35163846 ]
Pak S, Thapa B, Lee K: Decursinol Angelate Mitigates Sepsis Induced by Methicillin-Resistant Staphylococcus aureus Infection by Modulating the Inflammatory Responses of Macrophages. Int J Mol Sci. 2021 Oct 11;22(20). pii: ijms222010950. doi: 10.3390/ijms222010950. [PubMed:34681611 ]
Chang SN, Khan I, Kim CG, Park SM, Choi DK, Lee H, Hwang BS, Kang SC, Park JG: Decursinol Angelate Arrest Melanoma Cell Proliferation by Initiating Cell Death and Tumor Shrinkage via Induction of Apoptosis. Int J Mol Sci. 2021 Apr 15;22(8). pii: ijms22084096. doi: 10.3390/ijms22084096. [PubMed:33921050 ]
Tang SN, Jiang P, Kim S, Zhang J, Jiang C, Lu J: Interception Targets of Angelica Gigas Nakai Root Extract versus Pyranocoumarins in Prostate Early Lesions and Neuroendocrine Carcinomas in TRAMP Mice. Cancer Prev Res (Phila). 2021 Jun;14(6):635-648. doi: 10.1158/1940-6207.CAPR-20-0589. Epub 2021 Mar 1. [PubMed:33648943 ]
Sharma C, Kang SC: Molecular dynamic simulation (MDS) and in vitro cathepsin-B inhibitory activity of decrusin angelate, ibuprofen, and thymol. Nat Prod Res. 2022 Feb;36(4):1020-1025. doi: 10.1080/14786419.2020.1843030. Epub 2020 Nov 4. [PubMed:33148043 ]

Showing NP-Card for Decursinol (NP0051442)

MOL for NP0051442 (Decursinol)

3D MOL for NP0051442 (Decursinol)

3D SDF for NP0051442 (Decursinol)

3D-SDF for NP0051442 (Decursinol)

PDB for NP0051442 (Decursinol)

3D PDB for NP0051442 (Decursinol)

SMILES for NP0051442 (Decursinol)

INCHI for NP0051442 (Decursinol)

Structure for NP0051442 (Decursinol)

3D Structure for NP0051442 (Decursinol)