NP-MRD: Showing NP-Card for (2e)-3-(4-{[(1s,2s)-3-hydroxy-1-[(2-hydroxyethyl)amino]-1-(3,4,5-trimethoxyphenyl)propan-2-yl]oxy}-3,5-dimethoxyphenyl)prop-2-en-1-ol (NP0161152)

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Record Information

Version

2.0

Created at

2022-09-02 19:15:39 UTC

Updated at

2022-09-02 19:15:39 UTC

NP-MRD ID

NP0161152

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2e)-3-(4-{[(1s,2s)-3-hydroxy-1-[(2-hydroxyethyl)amino]-1-(3,4,5-trimethoxyphenyl)propan-2-yl]oxy}-3,5-dimethoxyphenyl)prop-2-en-1-ol

Description

Hispidacine belongs to the class of organic compounds known as dimethoxybenzenes. These are organic aromatic compounds containing a monocyclic benzene moiety carrying exactly two methoxy groups. (2e)-3-(4-{[(1s,2s)-3-hydroxy-1-[(2-hydroxyethyl)amino]-1-(3,4,5-trimethoxyphenyl)propan-2-yl]oxy}-3,5-dimethoxyphenyl)prop-2-en-1-ol is found in Medicago polymorpha. (2e)-3-(4-{[(1s,2s)-3-hydroxy-1-[(2-hydroxyethyl)amino]-1-(3,4,5-trimethoxyphenyl)propan-2-yl]oxy}-3,5-dimethoxyphenyl)prop-2-en-1-ol was first documented in 2015 (PMID: 25468714). Based on a literature review very few articles have been published on Hispidacine.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309022221152D          

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  Mrv1652309022221152D          

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 30 33  2  0  0  0  0
  3 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0161152

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(\C=C\CO)=CC(OC)=C1O[C@H](CO)[C@@H](NCCO)C1=CC(OC)=C(OC)C(OC)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C25H35NO9/c1-30-18-11-16(7-6-9-27)12-19(31-2)25(18)35-22(15-29)23(26-8-10-28)17-13-20(32-3)24(34-5)21(14-17)33-4/h6-7,11-14,22-23,26-29H,8-10,15H2,1-5H3/b7-6+/t22-,23+/m1/s1

> <INCHI_KEY>
PJHVGDSVHPBDFB-ZLHQQMCGSA-N

> <FORMULA>
C25H35NO9

> <MOLECULAR_WEIGHT>
493.553

> <EXACT_MASS>
493.231181711

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
70

> <JCHEM_AVERAGE_POLARIZABILITY>
52.916493880012766

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2E)-3-(4-{[(1S,2S)-3-hydroxy-1-[(2-hydroxyethyl)amino]-1-(3,4,5-trimethoxyphenyl)propan-2-yl]oxy}-3,5-dimethoxyphenyl)prop-2-en-1-ol

> <ALOGPS_LOGP>
1.46

> <JCHEM_LOGP>
0.969183946333333

> <ALOGPS_LOGS>
-3.96

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
15.366886641548188

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.520056489479643

> <JCHEM_PKA_STRONGEST_BASIC>
7.770277039479076

> <JCHEM_POLAR_SURFACE_AREA>
128.10000000000002

> <JCHEM_REFRACTIVITY>
131.2337

> <JCHEM_ROTATABLE_BOND_COUNT>
15

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.44e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2E)-3-(4-{[(1S,2S)-3-hydroxy-1-[(2-hydroxyethyl)amino]-1-(3,4,5-trimethoxyphenyl)propan-2-yl]oxy}-3,5-dimethoxyphenyl)prop-2-en-1-ol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 02-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-SEP-22         0                                  
HETATM    1  C   UNK     0      -1.334 -13.090   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -1.334 -11.550   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       0.000 -10.780   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000  -9.240   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334  -8.470   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0       0.000  -6.160   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.334  -3.850   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  C   UNK     0       2.667  -6.160   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       4.001  -8.470   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       4.001  -3.850   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       2.667  -1.540   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.335  -1.540   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       8.002  -1.540   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       8.002   0.000   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       9.336   0.770   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      10.669   0.000   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       6.668  -3.850   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       5.335  -6.160   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       6.668  -6.930   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       2.667  -9.240   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       2.667 -10.780   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       4.001 -11.550   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       4.001 -13.090   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       1.334 -11.550   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       1.334 -13.090   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0       0.000 -13.860   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   33                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   29                                                  
CONECT    6    5    7   11                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9                                                            
CONECT   11    6   12   14                                                  
CONECT   12   11   13                                                       
CONECT   13   12                                                            
CONECT   14   11   15                                                       
CONECT   15   14   16   26                                                  
CONECT   16   15   17   19                                                  
CONECT   17   16   18                                                       
CONECT   18   17                                                            
CONECT   19   16   20                                                       
CONECT   20   19   21   25                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23                                                            
CONECT   25   20   26                                                       
CONECT   26   25   15   27                                                  
CONECT   27   26   28                                                       
CONECT   28   27                                                            
CONECT   29    5   30                                                       
CONECT   30   29   31   33                                                  
CONECT   31   30   32                                                       
CONECT   32   31                                                            
CONECT   33   30    3   34                                                  
CONECT   34   33   35                                                       
CONECT   35   34                                                            
MASTER        0    0    0    0    0    0    0    0   35    0   72    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₅H₃₅NO₉

Average Mass

493.5530 Da

Monoisotopic Mass

493.23118 Da

IUPAC Name

(2E)-3-(4-{[(1S,2S)-3-hydroxy-1-[(2-hydroxyethyl)amino]-1-(3,4,5-trimethoxyphenyl)propan-2-yl]oxy}-3,5-dimethoxyphenyl)prop-2-en-1-ol

Traditional Name

(2E)-3-(4-{[(1S,2S)-3-hydroxy-1-[(2-hydroxyethyl)amino]-1-(3,4,5-trimethoxyphenyl)propan-2-yl]oxy}-3,5-dimethoxyphenyl)prop-2-en-1-ol

CAS Registry Number

Not Available

SMILES

COC1=CC(\C=C\CO)=CC(OC)=C1O[C@H](CO)[C@@H](NCCO)C1=CC(OC)=C(OC)C(OC)=C1

InChI Identifier

InChI=1S/C25H35NO9/c1-30-18-11-16(7-6-9-27)12-19(31-2)25(18)35-22(15-29)23(26-8-10-28)17-13-20(32-3)24(34-5)21(14-17)33-4/h6-7,11-14,22-23,26-29H,8-10,15H2,1-5H3/b7-6+/t22-,23+/m1/s1

InChI Key

PJHVGDSVHPBDFB-ZLHQQMCGSA-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
Medicago polymorpha	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as dimethoxybenzenes. These are organic aromatic compounds containing a monocyclic benzene moiety carrying exactly two methoxy groups.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Methoxybenzenes

Direct Parent

Dimethoxybenzenes

Alternative Parents

Substituents

Cinnamyl alcohol
Dimethoxybenzene
M-dimethoxybenzene
Anisole
Phenol ether
Styrene
Phenoxy compound
Aralkylamine
Alkyl aryl ether
1,3-aminoalcohol
1,2-aminoalcohol
Alkanolamine
Secondary amine
Ether
Secondary aliphatic amine
Hydrocarbon derivative
Organic nitrogen compound
Organonitrogen compound
Amine
Organooxygen compound
Primary alcohol
Alcohol
Organic oxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic 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	1.46	ALOGPS
logP	0.97	ChemAxon
logS	-4	ALOGPS
pKa (Strongest Acidic)	14.52	ChemAxon
pKa (Strongest Basic)	7.77	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	128.1 Å²	ChemAxon
Rotatable Bond Count	15	ChemAxon
Refractivity	131.23 m³·mol⁻¹	ChemAxon
Polarizability	52.92 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	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

Not Available

Chemspider ID

58838729

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

101883143

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Yap VA, Loong BJ, Ting KN, Loh SH, Yong KT, Low YY, Kam TS, Lim KH: Hispidacine, an unusual 8,4'-oxyneolignan-alkaloid with vasorelaxant activity, and hispiloscine, an antiproliferative phenanthroindolizidine alkaloid, from Ficus hispida Linn. Phytochemistry. 2015 Jan;109:96-102. doi: 10.1016/j.phytochem.2014.10.032. Epub 2014 Nov 19. [PubMed:25468714 ]
LOTUS database [Link]

Showing NP-Card for (2e)-3-(4-{[(1s,2s)-3-hydroxy-1-[(2-hydroxyethyl)amino]-1-(3,4,5-trimethoxyphenyl)propan-2-yl]oxy}-3,5-dimethoxyphenyl)prop-2-en-1-ol (NP0161152)

MOL for NP0161152 ((2e)-3-(4-{[(1s,2s)-3-hydroxy-1-[(2-hydroxyethyl)amino]-1-(3,4,5-trimethoxyphenyl)propan-2-yl]oxy}-3,5-dimethoxyphenyl)prop-2-en-1-ol)

3D MOL for NP0161152 ((2e)-3-(4-{[(1s,2s)-3-hydroxy-1-[(2-hydroxyethyl)amino]-1-(3,4,5-trimethoxyphenyl)propan-2-yl]oxy}-3,5-dimethoxyphenyl)prop-2-en-1-ol)

3D SDF for NP0161152 ((2e)-3-(4-{[(1s,2s)-3-hydroxy-1-[(2-hydroxyethyl)amino]-1-(3,4,5-trimethoxyphenyl)propan-2-yl]oxy}-3,5-dimethoxyphenyl)prop-2-en-1-ol)

3D-SDF for NP0161152 ((2e)-3-(4-{[(1s,2s)-3-hydroxy-1-[(2-hydroxyethyl)amino]-1-(3,4,5-trimethoxyphenyl)propan-2-yl]oxy}-3,5-dimethoxyphenyl)prop-2-en-1-ol)

PDB for NP0161152 ((2e)-3-(4-{[(1s,2s)-3-hydroxy-1-[(2-hydroxyethyl)amino]-1-(3,4,5-trimethoxyphenyl)propan-2-yl]oxy}-3,5-dimethoxyphenyl)prop-2-en-1-ol)

3D PDB for NP0161152 ((2e)-3-(4-{[(1s,2s)-3-hydroxy-1-[(2-hydroxyethyl)amino]-1-(3,4,5-trimethoxyphenyl)propan-2-yl]oxy}-3,5-dimethoxyphenyl)prop-2-en-1-ol)

SMILES for NP0161152 ((2e)-3-(4-{[(1s,2s)-3-hydroxy-1-[(2-hydroxyethyl)amino]-1-(3,4,5-trimethoxyphenyl)propan-2-yl]oxy}-3,5-dimethoxyphenyl)prop-2-en-1-ol)

INCHI for NP0161152 ((2e)-3-(4-{[(1s,2s)-3-hydroxy-1-[(2-hydroxyethyl)amino]-1-(3,4,5-trimethoxyphenyl)propan-2-yl]oxy}-3,5-dimethoxyphenyl)prop-2-en-1-ol)

Structure for NP0161152 ((2e)-3-(4-{[(1s,2s)-3-hydroxy-1-[(2-hydroxyethyl)amino]-1-(3,4,5-trimethoxyphenyl)propan-2-yl]oxy}-3,5-dimethoxyphenyl)prop-2-en-1-ol)

3D Structure for NP0161152 ((2e)-3-(4-{[(1s,2s)-3-hydroxy-1-[(2-hydroxyethyl)amino]-1-(3,4,5-trimethoxyphenyl)propan-2-yl]oxy}-3,5-dimethoxyphenyl)prop-2-en-1-ol)