NP-MRD: Showing NP-Card for Dihydrodehydrodiconiferyl alcohol (NP0050451)

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Record Information

Version

2.0

Created at

2022-04-27 21:39:55 UTC

Updated at

2022-04-27 21:39:55 UTC

NP-MRD ID

NP0050451

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Dihydrodehydrodiconiferyl alcohol

Description

Dihydrodehydrodiconiferyl alcohol belongs to the class of organic compounds known as 2-arylbenzofuran flavonoids. These are phenylpropanoids containing the 2-phenylbenzofuran moiety. Dihydrodehydrodiconiferyl alcohol is found in Aconitum baicalense, Annona squamosa, Berberis koreana, Betula maximowicziana, Brosimum acutifolium, Bursera tonkinensis, Cleistopholis glauca, Cycas circinalis, Acanthopanax senticosus , Epimedium sagittatum, Eucommia ulmoides , Euonymus alatus, Helicteres angustifolia , Hibiscus taiwanensis, Juniperus chinensis, Magnolia coco, Mitragyna africanus, Picea glauca, Picea glehnii, Rosa canina, Santalum album L. , Sarcandra glabra , Streblus asper, Taraxacum alpinum, Vitex agnus-castus, Vitex negundo and Vitex rotundifolia. Dihydrodehydrodiconiferyl alcohol was first documented in 2018 (PMID: 30413192). Dihydrodehydrodiconiferyl alcohol is an extremely weak basic (essentially neutral) compound (based on its pKa) (PMID: 32962016) (PMID: 31948026) (PMID: 31857179) (PMID: 30693991).

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309272006312D          

 26 28  0  0  0  0            999 V2000
 9999.301310000.3881    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.447810000.8813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.8704 9997.9125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.1560 9998.3258    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.4416 9997.9125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9995.7272 9998.3258    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9999.2999 9999.5631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.5855 9999.1506    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.5855 9998.3255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.2999 9997.9130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.7999 9999.4055    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10000.0153 9999.1505    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.0153 9998.3255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.7999 9998.0706    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10001.2848 9998.7380    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10001.8619 9997.1145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10001.0549 9997.2860    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.7599 9998.7380    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.3474 9999.4524    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.5223 9999.4524    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.1098 9998.7380    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.5223 9998.0235    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.3474 9998.0235    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.759910000.1669    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10003.347410000.8814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10004.5849 9998.7381    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  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
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  7  1  1  0  0  0  0
  9  3  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 11 12  1  0  0  0  0
 11 15  1  0  0  0  0
 14 17  1  1  0  0  0
 17 16  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 18  1  0  0  0  0
 15 21  1  6  0  0  0
 18 26  1  0  0  0  0
 19 24  1  0  0  0  0
 24 25  1  0  0  0  0
 12  7  1  0  0  0  0
 10 13  1  0  0  0  0
M  END


  Mrv1652309272006312D          

 26 28  0  0  0  0            999 V2000
 9999.301310000.3881    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.447810000.8813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.8704 9997.9125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.1560 9998.3258    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.4416 9997.9125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9995.7272 9998.3258    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9999.2999 9999.5631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.5855 9999.1506    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.5855 9998.3255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.2999 9997.9130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.7999 9999.4055    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10000.0153 9999.1505    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.0153 9998.3255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.7999 9998.0706    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10001.2848 9998.7380    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10001.8619 9997.1145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10001.0549 9997.2860    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.7599 9998.7380    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.3474 9999.4524    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.5223 9999.4524    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.1098 9998.7380    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.5223 9998.0235    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.3474 9998.0235    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.759910000.1669    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10003.347410000.8814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10004.5849 9998.7381    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  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
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  7  1  1  0  0  0  0
  9  3  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 11 12  1  0  0  0  0
 11 15  1  0  0  0  0
 14 17  1  1  0  0  0
 17 16  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 18  1  0  0  0  0
 15 21  1  6  0  0  0
 18 26  1  0  0  0  0
 19 24  1  0  0  0  0
 24 25  1  0  0  0  0
 12  7  1  0  0  0  0
 10 13  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0050451

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(CCCO)=CC2=C1O[C@@H]([C@H]2CO)C1=CC(OC)=C(O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C20H24O6/c1-24-17-10-13(5-6-16(17)23)19-15(11-22)14-8-12(4-3-7-21)9-18(25-2)20(14)26-19/h5-6,8-10,15,19,21-23H,3-4,7,11H2,1-2H3/t15-,19+/m0/s1

> <INCHI_KEY>
SBLZVJIHPWRSQQ-HNAYVOBHSA-N

> <FORMULA>
C20H24O6

> <MOLECULAR_WEIGHT>
360.406

> <EXACT_MASS>
360.157288493

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
50

> <JCHEM_AVERAGE_POLARIZABILITY>
38.91567003214111

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-[(2S,3R)-3-(hydroxymethyl)-5-(3-hydroxypropyl)-7-methoxy-2,3-dihydro-1-benzofuran-2-yl]-2-methoxyphenol

> <ALOGPS_LOGP>
2.24

> <JCHEM_LOGP>
1.956526430333334

> <ALOGPS_LOGS>
-3.87

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.131312234490373

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.909971918704782

> <JCHEM_PKA_STRONGEST_BASIC>
-2.3774160823365182

> <JCHEM_POLAR_SURFACE_AREA>
88.38000000000001

> <JCHEM_REFRACTIVITY>
97.4943

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.84e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-[(2S,3R)-3-(hydroxymethyl)-5-(3-hydroxypropyl)-7-methoxy-2,3-dihydro-1-benzofuran-2-yl]-2-methoxyphenol

> <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    8665.3628667.391   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0    8663.7698668.312   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0    8662.6918662.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0    8661.3588663.541   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0    8660.0248662.770   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0    8658.6918663.541   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0    8665.3608665.851   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    8664.0268665.081   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8664.0268663.541   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8665.3608662.771   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0    8668.1608665.557   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0    8666.6958665.081   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8666.6958663.541   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8668.1608663.065   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8669.0658664.311   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0    8670.1428661.280   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0    8668.6368661.601   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0    8673.6858664.311   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0    8672.9158665.644   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0    8671.3758665.644   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0    8670.6058664.311   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0    8671.3758662.977   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0    8672.9158662.977   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0    8673.6858666.978   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0    8672.9158668.312   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0    8675.2258664.311   0.000  0.00  0.00           O+0
CONECT    1    2    7                                                       
CONECT    2    1                                                            
CONECT    3    4    9                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5                                                            
CONECT    7    8    1   12                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10    3                                                  
CONECT   10    9   13                                                       
CONECT   11   12   15                                                       
CONECT   12   13   11    7                                                  
CONECT   13   12   14   10                                                  
CONECT   14   13   15   17                                                  
CONECT   15   14   11   21                                                  
CONECT   16   17                                                            
CONECT   17   14   16                                                       
CONECT   18   19   23   26                                                  
CONECT   19   18   20   24                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22   15                                                  
CONECT   22   21   23                                                       
CONECT   23   22   18                                                       
CONECT   24   19   25                                                       
CONECT   25   24                                                            
CONECT   26   18                                                            
MASTER        0    0    0    0    0    0    0    0   26    0   56    0
END

View in JSmol

Synonyms

Value	Source
(+)-Dihydrodehydrodiconiferyl alcohol	PhytoBank
(2S,3R)-Dihydrodehydroconiferyl alcohol	PhytoBank
(7S,8R)-Dihydrodehydrodiconiferyl alcohol	PhytoBank
(7S,8R)-Lawsonicin	PhytoBank
Dehydroconiferyl alcohol	PhytoBank

Chemical Formula

C₂₀H₂₄O₆

Average Mass

360.4060 Da

Monoisotopic Mass

360.15729 Da

IUPAC Name

4-[(2S,3R)-3-(hydroxymethyl)-5-(3-hydroxypropyl)-7-methoxy-2,3-dihydro-1-benzofuran-2-yl]-2-methoxyphenol

Traditional Name

4-[(2S,3R)-3-(hydroxymethyl)-5-(3-hydroxypropyl)-7-methoxy-2,3-dihydro-1-benzofuran-2-yl]-2-methoxyphenol

CAS Registry Number

Not Available

SMILES

COC1=CC(CCCO)=CC2=C1O[C@@H]([C@H]2CO)C1=CC(OC)=C(O)C=C1

InChI Identifier

InChI=1S/C20H24O6/c1-24-17-10-13(5-6-16(17)23)19-15(11-22)14-8-12(4-3-7-21)9-18(25-2)20(14)26-19/h5-6,8-10,15,19,21-23H,3-4,7,11H2,1-2H3/t15-,19+/m0/s1

InChI Key

SBLZVJIHPWRSQQ-HNAYVOBHSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Aconitum baicalense	LOTUS Database	35616633
Annona squamosa	LOTUS Database	35616633
Berberis koreana	LOTUS Database	35616633
Betula maximowicziana	LOTUS Database	35616633
Brosimum acutifolium	LOTUS Database	35616633
Bursera tonkinensis	LOTUS Database	35616633
Cleistopholis glauca	LOTUS Database	35616633
Cycas circinalis	LOTUS Database	35616633
Eleutherococcus senticosus	Plant	KNApSAcK
Epimedium sagittatum	LOTUS Database	35616633
Eucommia ulmoides	Plant	KNApSAcK
Euonymus alatus	LOTUS Database	35616633
Helicteres angustifolia	Plant	KNApSAcK
Hibiscus taiwanensis	Plant	KNApSAcK
Juniperus chinensis	LOTUS Database	35616633
Magnolia coco	LOTUS Database	35616633
Mitragyna africanus	Plant	KNApSAcK
Picea glauca	LOTUS Database	35616633
Picea glehnii	LOTUS Database	35616633
Rosa canina	LOTUS Database	35616633
Santalum album	Plant	KNApSAcK
Sarcandra glabra	Plant	KNApSAcK
Streblus asper	LOTUS Database	35616633
Taraxacum alpinum	LOTUS Database	35616633
Vitex agnus-castus	LOTUS Database	35616633
Vitex negundo	LOTUS Database	35616633
Vitex rotundifolia	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 2-arylbenzofuran flavonoids. These are phenylpropanoids containing the 2-phenylbenzofuran moiety.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

2-arylbenzofuran flavonoids

Sub Class

Not Available

Direct Parent

2-arylbenzofuran flavonoids

Alternative Parents

Substituents

2-arylbenzofuran flavonoid
Norlignan skeleton
Neolignan skeleton
Methoxyphenol
Coumaran
Benzofuran
Phenoxy compound
Anisole
Methoxybenzene
Phenol ether
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Phenol
Monocyclic benzene moiety
Benzenoid
Oxacycle
Organoheterocyclic compound
Ether
Organic oxygen compound
Alcohol
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
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	2.24	ALOGPS
logP	1.96	ChemAxon
logS	-3.9	ALOGPS
pKa (Strongest Acidic)	9.91	ChemAxon
pKa (Strongest Basic)	-2.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	88.38 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	97.49 m³·mol⁻¹	ChemAxon
Polarizability	38.92 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	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

340859

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

384679

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Qi Y, Choi SI, Son SR, Han HS, Ahn HS, Shin YK, Lee SH, Lee KT, Kwon HC, Jang DS: Chemical Constituents of the Leaves of Campanula takesimana (Korean Bellflower) and Their Inhibitory Effects on LPS-induced PGE2 Production. Plants (Basel). 2020 Sep 18;9(9). pii: plants9091232. doi: 10.3390/plants9091232. [PubMed:32962016 ]
Li S, Zhao C, Yue F, Lu F: Revealing Structural Modifications of Lignin in Acidic gamma-Valerolactone-H(2)O Pretreatment. Polymers (Basel). 2020 Jan 5;12(1):116. doi: 10.3390/polym12010116. [PubMed:31948026 ]
Chang CC, Tsai WT, Chen CK, Chen CH, Lee SS: Diastereomeric identification of neolignan rhamnosides from Trochodendron aralioides leaves by LC-SPE-NMR and circular dichroism. Fitoterapia. 2020 Jul;144:104455. doi: 10.1016/j.fitote.2019.104455. Epub 2019 Dec 17. [PubMed:31857179 ]
Li M, Li B, Hou Y, Tian Y, Chen L, Liu S, Zhang N, Dong J: Anti-inflammatory effects of chemical components from Ginkgo biloba L. male flowers on lipopolysaccharide-stimulated RAW264.7 macrophages. Phytother Res. 2019 Apr;33(4):989-997. doi: 10.1002/ptr.6292. Epub 2019 Jan 29. [PubMed:30693991 ]
Thabet AA, Youssef FS, Korinek M, Chang FR, Wu YC, Chen BH, El-Shazly M, Singab ANB, Hwang TL: Study of the anti-allergic and anti-inflammatory activity of Brachychiton rupestris and Brachychiton discolor leaves (Malvaceae) using in vitro models. BMC Complement Altern Med. 2018 Nov 9;18(1):299. doi: 10.1186/s12906-018-2359-6. [PubMed:30413192 ]

Showing NP-Card for Dihydrodehydrodiconiferyl alcohol (NP0050451)

MOL for NP0050451 (Dihydrodehydrodiconiferyl alcohol)

3D MOL for NP0050451 (Dihydrodehydrodiconiferyl alcohol)

3D SDF for NP0050451 (Dihydrodehydrodiconiferyl alcohol)

3D-SDF for NP0050451 (Dihydrodehydrodiconiferyl alcohol)

PDB for NP0050451 (Dihydrodehydrodiconiferyl alcohol)

3D PDB for NP0050451 (Dihydrodehydrodiconiferyl alcohol)

SMILES for NP0050451 (Dihydrodehydrodiconiferyl alcohol)

INCHI for NP0050451 (Dihydrodehydrodiconiferyl alcohol)

Structure for NP0050451 (Dihydrodehydrodiconiferyl alcohol)

3D Structure for NP0050451 (Dihydrodehydrodiconiferyl alcohol)