NP-MRD: Showing NP-Card for Dihydroconiferyl alcohol (NP0002803)

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Record Information

Version

1.0

Created at

2020-11-23 19:40:50 UTC

Updated at

2021-08-19 23:59:24 UTC

NP-MRD ID

NP0002803

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Dihydroconiferyl alcohol

Provided By

BMRB

Description

Dihydroconiferyl alcohol, also known as 3-(4-guaiacyl)propanol or 4-(3-hydroxypropyl)guaiacol, belongs to the class of organic compounds known as methoxyphenols. Methoxyphenols are compounds containing a methoxy group attached to the benzene ring of a phenol moiety. Dihydroconiferyl alcohol 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. Dihydroconiferyl alcohol is found in Abies spectabilis, Aconitum baicalense, Ailanthus altissima, Bongardia chrysogonum, Broussonetia papyrifera, Bulbophyllum protractum, Euterpe oleracea, Larix kaempferi, Licaria chrysophylla, Picea glauca, Picea jezoensis, Pinus contorta, Pinus densiflora, Taxus baccata, Taxus mairei and Tsuga chinensis. It was first documented in 2008 (PMID: 17984079). Based on a literature review very few articles have been published on Dihydroconiferyl alcohol (PMID: 21664814) (PMID: 23944031).

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI


     RDKit          2D

 27 27  0  0  0  0  0  0  0  0999 V2000
    3.1169   -2.5726    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5742   -1.1440    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5656   -0.0337    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0997   -0.3520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0912    0.7583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3747    0.4400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8405    0.1217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3064   -0.1966    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7722   -0.5149    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5484    2.1869    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0142    2.5052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0228    1.3949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4887    1.7132    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5455   -3.0298    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6883   -2.1153    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6597   -4.0012    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6425   -1.7806    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6930    1.9058    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0564   -1.0258    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1588    1.5875    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5222   -1.3442    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9880   -1.6625    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6247    1.2692    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2294   -1.9436    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4602    3.2972    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4715    3.9338    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4973    0.6029    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  5 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 12  3  1  0
  1 14  1  1
  1 15  1  0
  1 16  1  0
  4 17  1  0
  6 18  1  1
  6 19  1  0
  7 20  1  1
  7 21  1  0
  8 22  1  1
  8 23  1  0
  9 24  1  0
 10 25  1  0
 11 26  1  0
 13 27  1  0
M  END
> <DATABASE_ID>
NP0002803

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(CCCO)=CC=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C10H14O3/c1-13-10-7-8(3-2-6-11)4-5-9(10)12/h4-5,7,11-12H,2-3,6H2,1H3

> <INCHI_KEY>
MWOMNLDJNQWJMK-UHFFFAOYSA-N

> <FORMULA>
C10H14O3

> <MOLECULAR_WEIGHT>
182.2164

> <EXACT_MASS>
182.094294314

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
27

> <JCHEM_AVERAGE_POLARIZABILITY>
19.83748758400574

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-(3-hydroxypropyl)-2-methoxyphenol

> <ALOGPS_LOGP>
1.25

> <JCHEM_LOGP>
1.4778893313333332

> <ALOGPS_LOGS>
-1.92

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.96338457216963

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.278286203919018

> <JCHEM_PKA_STRONGEST_BASIC>
-2.3774159967318234

> <JCHEM_POLAR_SURFACE_AREA>
49.69

> <JCHEM_REFRACTIVITY>
50.67400000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.18e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
dihydroconiferyl alcohol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 27-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-SEP-20         0                                  
HETATM    1  O   UNK     0    8657.8988658.011   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0    8660.5698661.091   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0    8659.2358660.321   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0    8659.2358658.781   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0    8660.5688658.011   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0    8661.9028658.781   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0    8661.9028660.321   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    8663.2368661.091   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8664.5698660.321   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8665.9028661.091   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0    8667.2358660.321   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0    8660.5688656.472   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0    8661.9018655.702   0.000  0.00  0.00           C+0
CONECT    1    4                                                            
CONECT    2    3    7                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5    1                                                  
CONECT    5    4    6   12                                                  
CONECT    6    5    7                                                       
CONECT    7    8    2    6                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10                                                            
CONECT   12    5   13                                                       
CONECT   13   12                                                            
MASTER        0    0    0    0    0    0    0    0   13    0   26    0
END

COMPND    NP0002803
HETATM    1  C1  UNL     1      -3.239  -1.683   0.733  1.00  0.00           C  
HETATM    2  O1  UNL     1      -3.346  -0.314   0.434  1.00  0.00           O  
HETATM    3  C2  UNL     1      -2.230   0.407   0.042  1.00  0.00           C  
HETATM    4  C3  UNL     1      -1.008  -0.221  -0.055  1.00  0.00           C  
HETATM    5  C4  UNL     1       0.159   0.409  -0.436  1.00  0.00           C  
HETATM    6  C5  UNL     1       1.447  -0.331  -0.520  1.00  0.00           C  
HETATM    7  C6  UNL     1       2.202  -0.292   0.803  1.00  0.00           C  
HETATM    8  C7  UNL     1       3.482  -1.073   0.588  1.00  0.00           C  
HETATM    9  O2  UNL     1       4.267  -1.111   1.735  1.00  0.00           O  
HETATM   10  C8  UNL     1       0.078   1.752  -0.734  1.00  0.00           C  
HETATM   11  C9  UNL     1      -1.130   2.414  -0.648  1.00  0.00           C  
HETATM   12  C10 UNL     1      -2.280   1.750  -0.263  1.00  0.00           C  
HETATM   13  O3  UNL     1      -3.501   2.396  -0.170  1.00  0.00           O  
HETATM   14  H1  UNL     1      -2.690  -2.265  -0.024  1.00  0.00           H  
HETATM   15  H2  UNL     1      -2.758  -1.828   1.744  1.00  0.00           H  
HETATM   16  H3  UNL     1      -4.275  -2.114   0.753  1.00  0.00           H  
HETATM   17  H4  UNL     1      -0.912  -1.286   0.175  1.00  0.00           H  
HETATM   18  H5  UNL     1       1.270  -1.378  -0.765  1.00  0.00           H  
HETATM   19  H6  UNL     1       2.133   0.100  -1.280  1.00  0.00           H  
HETATM   20  H7  UNL     1       1.597  -0.747   1.623  1.00  0.00           H  
HETATM   21  H8  UNL     1       2.422   0.773   1.003  1.00  0.00           H  
HETATM   22  H9  UNL     1       3.191  -2.080   0.230  1.00  0.00           H  
HETATM   23  H10 UNL     1       4.047  -0.539  -0.210  1.00  0.00           H  
HETATM   24  H11 UNL     1       4.871  -1.870   1.768  1.00  0.00           H  
HETATM   25  H12 UNL     1       0.992   2.269  -1.038  1.00  0.00           H  
HETATM   26  H13 UNL     1      -1.193   3.476  -0.884  1.00  0.00           H  
HETATM   27  H14 UNL     1      -3.596   3.384  -0.382  1.00  0.00           H  
CONECT    1    2   14   15   16
CONECT    2    3
CONECT    3    4    4   12
CONECT    4    5   17
CONECT    5    6   10   10
CONECT    6    7   18   19
CONECT    7    8   20   21
CONECT    8    9   22   23
CONECT    9   24
CONECT   10   11   25
CONECT   11   12   12   26
CONECT   12   13
CONECT   13   27
END

View in JSmol

Synonyms

Value	Source
3-(4-Guaiacyl)propanol	ChEBI
3-(4-Hydroxy-3-methoxyphenyl)-propan-1-ol	ChEBI
Guaiacyl propanol	ChEBI
4-Hydroxy-3-methoxy-benzenepropanol	Kegg
4-Hydroxy-3-methoxybenzenepropanol	HMDB
1-Guaiacyl-3-propanol	HMDB
3-(3-Methoxy-4-hydroxyphenyl)-1-propanol	HMDB
3-(3-Methoxy-4-hydroxyphenyl)propanol	HMDB
3-(4-Hydroxy-3-methoxyphenyl)-1-propanol	HMDB
3-(4-Hydroxy-3-methoxyphenyl)propanol	HMDB
3-(p-Hydroxy-m-methoxyphenyl)-1-propanol	HMDB
3-Guaiacyl-1-propanol	HMDB
4-(3-Hydroxypropyl)-2-methoxyphenol	HMDB
4-(3-Hydroxypropyl)guaiacol	HMDB
4-(gamma-Hydroxypropyl)-2-methoxyphenol	HMDB
4-(Γ-hydroxypropyl)-2-methoxyphenol	HMDB
4-Propanolguaiacol	HMDB
DHCA	HMDB
Guaiacyl-3-propanol	HMDB

Chemical Formula

C₁₀H₁₄O₃

Average Mass

182.2164 Da

Monoisotopic Mass

182.09429 Da

IUPAC Name

4-(3-hydroxypropyl)-2-methoxyphenol

Traditional Name

dihydroconiferyl alcohol

CAS Registry Number

Not Available

SMILES

COC1=CC(CCCO)=CC=C1O

InChI Identifier

InChI=1S/C10H14O3/c1-13-10-7-8(3-2-6-11)4-5-9(10)12/h4-5,7,11-12H,2-3,6H2,1H3

InChI Key

MWOMNLDJNQWJMK-UHFFFAOYSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 500 MHz, DMSO, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, DMSO, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, DMSO, experimental)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Abies spectabilis	LOTUS Database	35616633
Aconitum baicalense	LOTUS Database	35616633
Ailanthus altissima	LOTUS Database	35616633
Bongardia chrysogonum	LOTUS Database	35616633
Broussonetia papyrifera	LOTUS Database	35616633
Bulbophyllum protractum	LOTUS Database	35616633
Euterpe oleracea	LOTUS Database	35616633
Lactuca sativa	KNApSAcK Database	22123792
Larix kaempferi	LOTUS Database	35616633
Licaria chrysophylla	LOTUS Database	35616633
Picea glauca	LOTUS Database	35616633
Picea jezoensis	LOTUS Database	35616633
Pinus contorta	LOTUS Database	35616633
Pinus densiflora	LOTUS Database	35616633
Taxus baccata	LOTUS Database	35616633
Taxus mairei	LOTUS Database	35616633
Tsuga chinensis	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as methoxyphenols. Methoxyphenols are compounds containing a methoxy group attached to the benzene ring of a phenol moiety.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Phenols

Sub Class

Methoxyphenols

Direct Parent

Methoxyphenols

Alternative Parents

Not Available

Substituents

Not Available

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	65.00 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Boiling Point	339.00 to 340.00 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	11030 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	0.983 (est)	The Good Scents Company Information System

Predicted Properties

Property	Value	Source
logP	1.25	ALOGPS
logP	1.48	ChemAxon
logS	-1.9	ALOGPS
pKa (Strongest Acidic)	10.28	ChemAxon
pKa (Strongest Basic)	-2.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	49.69 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	50.67 m³·mol⁻¹	ChemAxon
Polarizability	19.84 Å³	ChemAxon
Number of Rings	1	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

HMDB0303757

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

16822

PDB ID

Not Available

ChEBI ID

4559

Good Scents ID

rw1486411

References

General References

Ulrich EL, Akutsu H, Doreleijers JF, Harano Y, Ioannidis YE, Lin J, Livny M, Mading S, Maziuk D, Miller Z, Nakatani E, Schulte CF, Tolmie DE, Kent Wenger R, Yao H, Markley JL: BioMagResBank. Nucleic Acids Res. 2008 Jan;36(Database issue):D402-8. doi: 10.1093/nar/gkm957. Epub 2007 Nov 4. [PubMed:17984079 ]
Torr KM, van de Pas DJ, Cazeils E, Suckling ID: Mild hydrogenolysis of in-situ and isolated Pinus radiata lignins. Bioresour Technol. 2011 Aug;102(16):7608-11. doi: 10.1016/j.biortech.2011.05.040. Epub 2011 May 27. [PubMed:21664814 ]
Wang XL, Chen MH, Wang F, Bu PB, Lin S, Zhu CG, Li YH, Jiang JD, Shi JG: [Chemical consitituents from root of Isatis indigotica]. Zhongguo Zhong Yao Za Zhi. 2013 Apr;38(8):1172-82. [PubMed:23944031 ]

Showing NP-Card for Dihydroconiferyl alcohol (NP0002803)

MOL for NP0002803 (Dihydroconiferyl alcohol)

3D MOL for NP0002803 (Dihydroconiferyl alcohol)

3D SDF for NP0002803 (Dihydroconiferyl alcohol)

3D-SDF for NP0002803 (Dihydroconiferyl alcohol)

PDB for NP0002803 (Dihydroconiferyl alcohol)

3D PDB for NP0002803 (Dihydroconiferyl alcohol)

SMILES for NP0002803 (Dihydroconiferyl alcohol)

INCHI for NP0002803 (Dihydroconiferyl alcohol)

Structure for NP0002803 (Dihydroconiferyl alcohol)

3D Structure for NP0002803 (Dihydroconiferyl alcohol)