NP-MRD: Showing NP-Card for (-)-Devenyol (NP0078436)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

1.0

Created at

2022-04-28 23:31:07 UTC

Updated at

2022-04-28 23:31:07 UTC

NP-MRD ID

NP0078436

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(-)-Devenyol

Description

Devenyol belongs to the class of organic compounds known as 7-hydroxycoumarins. These are coumarins that contain one or more hydroxyl groups attached to the C7 position the coumarin skeleton. (-)-Devenyol is found in Seseli devenyense Simonkai. It was first documented in 2005 (PMID: 16309314). Based on a literature review a significant number of articles have been published on Devenyol (PMID: 35501128) (PMID: 35501127) (PMID: 35501126) (PMID: 33673195).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 35 36  0  0  0  0  0  0  0  0999 V2000
   -4.0668    0.5543    0.1743 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7129    0.0437    0.5338 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.7092   -1.4643    0.5387 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3550    0.4687    1.8095 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6603    0.5782   -0.5121 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.7849    1.9803   -0.3276 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3908    0.0660   -0.0543 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8901    0.2744   -0.6654 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2249    0.8568   -1.8358 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3017    1.3776   -2.6748 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5746    0.9423   -2.2321 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5728    0.4435   -1.4522 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2641   -0.1578   -0.2507 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2853   -0.6738    0.5576 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9153   -1.2627    1.7457 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5834   -1.3226    2.0902 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2291   -1.8693    3.1951 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7033   -0.8154    1.2742 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9700   -0.2384    0.1269 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7996    0.0805    0.8318 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1093    1.6620    0.2463 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2884    0.2490   -0.8715 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4517   -1.8065   -0.4820 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7144   -1.7871    0.8741 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9453   -1.7986    1.2855 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1310    0.6864    2.3828 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0960    0.2387   -1.4502 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2360    2.3938   -1.1044 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5061   -1.0782    0.0360 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2977    0.3392    1.0502 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6438    1.4234   -2.6151 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8167    1.4214   -3.1881 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6253    0.4878   -1.7208 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3032   -0.6060    0.2536 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6393   -1.6874    2.4304 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  1
  2  5  1  0
  5  6  1  0
  5  7  1  0
  7  8  1  0
  8 19  2  0
 19 18  1  0
 18 16  1  0
 16 17  2  0
 16 15  1  0
 15 14  2  0
 14 13  1  0
 13 12  2  0
 12 11  1  0
 11  9  2  0
  9 10  1  0
  9  8  1  0
 13 19  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  3 23  1  0
  3 24  1  0
  3 25  1  0
  4 26  1  0
  5 27  1  6
  6 28  1  0
  7 29  1  0
  7 30  1  0
 15 35  1  0
 14 34  1  0
 12 33  1  0
 11 32  1  0
 10 31  1  0
M  END


  Mrv1652304292201312D          

 19 20  0  0  1  0            999 V2000
   -0.7145   -0.4125    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
    0.0000   -1.6500    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
    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 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4289    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5395    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1105    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 O   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
    2.8579   -0.0000    0.0000 O   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   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.0000    0.0000 O   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
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  6  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
 10 13  1  0  0  0  0
  5 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
 17 18  2  0  0  0  0
  4 18  1  0  0  0  0
  1 19  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0078436

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)(O)[C@@H](O)CC1=C2OC(=O)C=CC2=CC=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C14H16O5/c1-14(2,18)11(16)7-9-10(15)5-3-8-4-6-12(17)19-13(8)9/h3-6,11,15-16,18H,7H2,1-2H3/t11-/m0/s1

> <INCHI_KEY>
BFYOVPHBKUQKPM-NSHDSACASA-N

> <FORMULA>
C14H16O5

> <MOLECULAR_WEIGHT>
264.277

> <EXACT_MASS>
264.099773615

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
35

> <JCHEM_AVERAGE_POLARIZABILITY>
26.603433586947773

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
8-[(2S)-2,3-dihydroxy-3-methylbutyl]-7-hydroxy-2H-chromen-2-one

> <ALOGPS_LOGP>
1.34

> <JCHEM_LOGP>
1.0679224823333329

> <ALOGPS_LOGS>
-2.38

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.736042152115637

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.064149105228424

> <JCHEM_PKA_STRONGEST_BASIC>
-3.0941120723013382

> <JCHEM_POLAR_SURFACE_AREA>
86.99

> <JCHEM_REFRACTIVITY>
70.1199

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.11e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
8-[(2S)-2,3-dihydroxy-3-methylbutyl]-7-hydroxychromen-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 29-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-APR-22         0                                  
HETATM    1  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -2.667   1.540   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.334   5.390   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -2.874   3.850   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       0.206   3.850   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       2.667  -0.000   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       5.335  -0.000   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -2.667   0.000   0.000  0.00  0.00           O+0
CONECT    1    2    6   19                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5   18                                                  
CONECT    5    4    6   14                                                  
CONECT    6    5    1    7                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   12   13                                             
CONECT   11   10                                                            
CONECT   12   10                                                            
CONECT   13   10                                                            
CONECT   14    5   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18                                                       
CONECT   18   17    4                                                       
CONECT   19    1                                                            
MASTER        0    0    0    0    0    0    0    0   19    0   40    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₄H₁₆O₅

Average Mass

264.2770 Da

Monoisotopic Mass

264.09977 Da

IUPAC Name

8-[(2S)-2,3-dihydroxy-3-methylbutyl]-7-hydroxy-2H-chromen-2-one

Traditional Name

8-[(2S)-2,3-dihydroxy-3-methylbutyl]-7-hydroxychromen-2-one

CAS Registry Number

Not Available

SMILES

CC(C)(O)[C@@H](O)CC1=C2OC(=O)C=CC2=CC=C1O

InChI Identifier

InChI=1S/C14H16O5/c1-14(2,18)11(16)7-9-10(15)5-3-8-4-6-12(17)19-13(8)9/h3-6,11,15-16,18H,7H2,1-2H3/t11-/m0/s1

InChI Key

BFYOVPHBKUQKPM-NSHDSACASA-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
Seseli devenyense Simonkai	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 7-hydroxycoumarins. These are coumarins that contain one or more hydroxyl groups attached to the C7 position the coumarin skeleton.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Coumarins and derivatives

Sub Class

Hydroxycoumarins

Direct Parent

7-hydroxycoumarins

Alternative Parents

Substituents

7-hydroxycoumarin
Benzopyran
1-benzopyran
1-hydroxy-2-unsubstituted benzenoid
Pyranone
Pyran
Benzenoid
Heteroaromatic compound
Tertiary alcohol
Secondary alcohol
1,2-diol
Lactone
Oxacycle
Organoheterocyclic compound
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Organic oxide
Alcohol
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	1.34	ALOGPS
logP	1.07	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Acidic)	8.06	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	86.99 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	70.12 m³·mol⁻¹	ChemAxon
Polarizability	26.6 Å³	ChemAxon
Number of Rings	2	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

C00042466

Chemspider ID

9797849

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11623101

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Booke F, Fauser D, Reims N, Bethge M: Unemployment due to the SARS-CoV-2-pandemic among people with and without severe disabilities: a difference-in-differences analysis. Occup Environ Med. 2022 May 2. pii: oemed-2021-108125. doi: 10.1136/oemed-2021-108125. [PubMed:35501128 ]
Ritonja JA, Aronson KJ, Leung M, Flaten L, Topouza DG, Duan QL, Durocher F, Tranmer JE, Bhatti P: Investigating the relationship between melatonin patterns and methylation in circadian genes among day shift and night shift workers. Occup Environ Med. 2022 May 2. pii: oemed-2021-108111. doi: 10.1136/oemed-2021-108111. [PubMed:35501127 ]
Kelly-Reif K, Bertke SJ, Samet J, Sood A, Schubauer-Berigan MK: Health burdens of uranium miners will extend beyond the radiation exposure compensation act deadline. Occup Environ Med. 2022 May 2. pii: oemed-2022-108311. doi: 10.1136/oemed-2022-108311. [PubMed:35501126 ]
Widelski J, Luca SV, Skiba A, Maciag M, Budzynska B, Marcourt L, Wolfender JL, Skalicka-Wozniak K: Coumarins from Seseli devenyense Simonk.: Isolation by Liquid-Liquid Chromatography and Potential Anxiolytic Activity Using an In Vivo Zebrafish Larvae Model. Int J Mol Sci. 2021 Feb 12;22(4). pii: ijms22041829. doi: 10.3390/ijms22041829. [PubMed:33673195 ]
Widelski J, Melliou E, Fokialakis N, Magiatis P, Glowniak K, Chinou I: Coumarins from the fruits of Seseli devenyense. J Nat Prod. 2005 Nov;68(11):1637-41. doi: 10.1021/np050209w. [PubMed:16309314 ]

Showing NP-Card for (-)-Devenyol (NP0078436)

MOL for NP0078436 ((-)-Devenyol)

3D MOL for NP0078436 ((-)-Devenyol)

3D SDF for NP0078436 ((-)-Devenyol)

3D-SDF for NP0078436 ((-)-Devenyol)

PDB for NP0078436 ((-)-Devenyol)

3D PDB for NP0078436 ((-)-Devenyol)

SMILES for NP0078436 ((-)-Devenyol)

INCHI for NP0078436 ((-)-Devenyol)

Structure for NP0078436 ((-)-Devenyol)

3D Structure for NP0078436 ((-)-Devenyol)