NP-MRD: Showing NP-Card for (1r,10r)-4-[(2e)-3,7-dimethylocta-2,6-dien-1-yl]-13-methyl-15-(3-methylbut-2-en-1-yl)-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-2(7),3,5,11,13,15-hexaene-5,14-diol (NP0249281)

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Record Information

Version

2.0

Created at

2022-09-07 11:47:18 UTC

Updated at

2022-09-07 11:47:18 UTC

NP-MRD ID

NP0249281

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r,10r)-4-[(2e)-3,7-dimethylocta-2,6-dien-1-yl]-13-methyl-15-(3-methylbut-2-en-1-yl)-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-2(7),3,5,11,13,15-hexaene-5,14-diol

Description

CHEMBL1835716 belongs to the class of organic compounds known as pterocarpans. These are benzo-pyrano-furano-benzene compounds, containing the 6H-[1]benzofuro[3,2-c]chromene skeleton. They are derivatives of isoflavonoids. (1r,10r)-4-[(2e)-3,7-dimethylocta-2,6-dien-1-yl]-13-methyl-15-(3-methylbut-2-en-1-yl)-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-2(7),3,5,11,13,15-hexaene-5,14-diol is found in Lespedeza bicolor. Based on a literature review very few articles have been published on CHEMBL1835716.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309072213472D          

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  Mrv1652309072213472D          

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 16 17  1  0  0  0  0
 14 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  1  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 23 25  2  0  0  0  0
 25 26  1  0  0  0  0
 25 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 30 31  1  0  0  0  0
 30 32  1  0  0  0  0
 27 33  2  0  0  0  0
 21 33  1  0  0  0  0
 33 34  1  0  0  0  0
 35 34  1  1  0  0  0
 13 35  1  0  0  0  0
 20 35  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0249281

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)=CCC\C(C)=C\CC1=CC2=C(OC[C@@H]3[C@H]2OC2=C(CC=C(C)C)C(O)=C(C)C=C32)C=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C31H38O4/c1-18(2)8-7-9-20(5)11-12-22-15-25-28(16-27(22)32)34-17-26-24-14-21(6)29(33)23(13-10-19(3)4)30(24)35-31(25)26/h8,10-11,14-16,26,31-33H,7,9,12-13,17H2,1-6H3/b20-11+/t26-,31-/m0/s1

> <INCHI_KEY>
HIFJVFRJNUZYGI-NVKVKWIFSA-N

> <FORMULA>
C31H38O4

> <MOLECULAR_WEIGHT>
474.641

> <EXACT_MASS>
474.277009704

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
73

> <JCHEM_AVERAGE_POLARIZABILITY>
56.18558828312378

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,10R)-4-[(2E)-3,7-dimethylocta-2,6-dien-1-yl]-13-methyl-15-(3-methylbut-2-en-1-yl)-8,17-dioxatetracyclo[8.7.0.0^{2,7}.0^{11,16}]heptadeca-2(7),3,5,11,13,15-hexaene-5,14-diol

> <JCHEM_LOGP>
7.993599003333333

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.800339053671019

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.08821149622257

> <JCHEM_PKA_STRONGEST_BASIC>
-4.587739917992832

> <JCHEM_POLAR_SURFACE_AREA>
58.92

> <JCHEM_REFRACTIVITY>
145.9082

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(1R,10R)-4-[(2E)-3,7-dimethylocta-2,6-dien-1-yl]-13-methyl-15-(3-methylbut-2-en-1-yl)-8,17-dioxatetracyclo[8.7.0.0^{2,7}.0^{11,16}]heptadeca-2(7),3,5,11,13,15-hexaene-5,14-diol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 07-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-SEP-22         0                                  
HETATM    1  C   UNK     0      18.178   1.529   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      16.640   1.617   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      15.795   0.330   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      15.948   2.993   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      14.410   3.081   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      13.718   4.456   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      12.180   4.544   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      11.488   5.920   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      11.335   3.257   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.798   3.345   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.953   2.057   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.415   2.146   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.570   0.858   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.263  -0.517   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.800  -0.606   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       9.645   0.682   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      11.183   0.594   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       6.418  -1.805   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       4.881  -1.717   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.188  -0.341   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.702   0.064   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       1.407  -0.768   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       0.038  -0.063   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -1.257  -0.895   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -0.035   1.476   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      -1.404   2.181   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       1.260   2.308   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       1.187   3.847   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -0.181   4.552   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -0.255   6.091   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -1.623   6.796   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       1.041   6.923   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       2.629   1.603   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       4.070   2.147   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0       5.033   0.946   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   16                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   35                                                  
CONECT   14   13   15   18                                                  
CONECT   15   14   16                                                       
CONECT   16   15   11   17                                                  
CONECT   17   16                                                            
CONECT   18   14   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21   35                                                  
CONECT   21   20   22   33                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28   33                                                  
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30                                                            
CONECT   33   27   21   34                                                  
CONECT   34   33   35                                                       
CONECT   35   34   13   20                                                  
MASTER        0    0    0    0    0    0    0    0   35    0   76    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₁H₃₈O₄

Average Mass

474.6410 Da

Monoisotopic Mass

474.27701 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

CC(C)=CCC\C(C)=C\CC1=CC2=C(OC[C@@H]3[C@H]2OC2=C(CC=C(C)C)C(O)=C(C)C=C32)C=C1O

InChI Identifier

InChI=1S/C31H38O4/c1-18(2)8-7-9-20(5)11-12-22-15-25-28(16-27(22)32)34-17-26-24-14-21(6)29(33)23(13-10-19(3)4)30(24)35-31(25)26/h8,10-11,14-16,26,31-33H,7,9,12-13,17H2,1-6H3/b20-11+/t26-,31-/m0/s1

InChI Key

HIFJVFRJNUZYGI-NVKVKWIFSA-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
Lespedeza bicolor	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pterocarpans. These are benzo-pyrano-furano-benzene compounds, containing the 6H-[1]benzofuro[3,2-c]chromene skeleton. They are derivatives of isoflavonoids.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Isoflavonoids

Sub Class

Furanoisoflavonoids

Direct Parent

Pterocarpans

Alternative Parents

Substituents

Pterocarpan
Isoflavanol
Isoflavan
Aromatic monoterpenoid
Chromane
1-benzopyran
Benzopyran
Monoterpenoid
Coumaran
Benzofuran
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Benzenoid
Oxacycle
Organoheterocyclic compound
Ether
Organic oxygen compound
Organooxygen compound
Hydrocarbon derivative
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

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

26636705

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

56665359

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1r,10r)-4-[(2e)-3,7-dimethylocta-2,6-dien-1-yl]-13-methyl-15-(3-methylbut-2-en-1-yl)-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-2(7),3,5,11,13,15-hexaene-5,14-diol (NP0249281)

MOL for NP0249281 ((1r,10r)-4-[(2e)-3,7-dimethylocta-2,6-dien-1-yl]-13-methyl-15-(3-methylbut-2-en-1-yl)-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-2(7),3,5,11,13,15-hexaene-5,14-diol)

3D MOL for NP0249281 ((1r,10r)-4-[(2e)-3,7-dimethylocta-2,6-dien-1-yl]-13-methyl-15-(3-methylbut-2-en-1-yl)-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-2(7),3,5,11,13,15-hexaene-5,14-diol)

3D SDF for NP0249281 ((1r,10r)-4-[(2e)-3,7-dimethylocta-2,6-dien-1-yl]-13-methyl-15-(3-methylbut-2-en-1-yl)-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-2(7),3,5,11,13,15-hexaene-5,14-diol)

3D-SDF for NP0249281 ((1r,10r)-4-[(2e)-3,7-dimethylocta-2,6-dien-1-yl]-13-methyl-15-(3-methylbut-2-en-1-yl)-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-2(7),3,5,11,13,15-hexaene-5,14-diol)

PDB for NP0249281 ((1r,10r)-4-[(2e)-3,7-dimethylocta-2,6-dien-1-yl]-13-methyl-15-(3-methylbut-2-en-1-yl)-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-2(7),3,5,11,13,15-hexaene-5,14-diol)

3D PDB for NP0249281 ((1r,10r)-4-[(2e)-3,7-dimethylocta-2,6-dien-1-yl]-13-methyl-15-(3-methylbut-2-en-1-yl)-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-2(7),3,5,11,13,15-hexaene-5,14-diol)

SMILES for NP0249281 ((1r,10r)-4-[(2e)-3,7-dimethylocta-2,6-dien-1-yl]-13-methyl-15-(3-methylbut-2-en-1-yl)-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-2(7),3,5,11,13,15-hexaene-5,14-diol)

INCHI for NP0249281 ((1r,10r)-4-[(2e)-3,7-dimethylocta-2,6-dien-1-yl]-13-methyl-15-(3-methylbut-2-en-1-yl)-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-2(7),3,5,11,13,15-hexaene-5,14-diol)

Structure for NP0249281 ((1r,10r)-4-[(2e)-3,7-dimethylocta-2,6-dien-1-yl]-13-methyl-15-(3-methylbut-2-en-1-yl)-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-2(7),3,5,11,13,15-hexaene-5,14-diol)

3D Structure for NP0249281 ((1r,10r)-4-[(2e)-3,7-dimethylocta-2,6-dien-1-yl]-13-methyl-15-(3-methylbut-2-en-1-yl)-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-2(7),3,5,11,13,15-hexaene-5,14-diol)