NP-MRD: Showing NP-Card for (1r,10s)-6,13-bis(3-methylbut-2-en-1-yl)-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-2,4,6,11(16),12,14-hexaene-5,14-diol (NP0222340)

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Record Information

Version

2.0

Created at

2022-09-06 00:09:04 UTC

Updated at

2022-09-06 00:09:04 UTC

NP-MRD ID

NP0222340

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r,10s)-6,13-bis(3-methylbut-2-en-1-yl)-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-2,4,6,11(16),12,14-hexaene-5,14-diol

Description

(1R,10S)-6,13-bis(3-methylbut-2-en-1-yl)-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]Heptadeca-2(7),3,5,11(16),12,14-hexaene-5,14-diol 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,10s)-6,13-bis(3-methylbut-2-en-1-yl)-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-2,4,6,11(16),12,14-hexaene-5,14-diol is found in Erythrina sigmoidea. Based on a literature review very few articles have been published on (1R,10S)-6,13-bis(3-methylbut-2-en-1-yl)-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]Heptadeca-2(7),3,5,11(16),12,14-hexaene-5,14-diol.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309062202092D          

 29 32  0  0  1  0            999 V2000
   -1.8544   -4.9946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8936   -4.1705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6269   -3.7925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1995   -3.7245    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4663   -4.1026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2278   -3.6566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9611   -4.0347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6551   -3.5887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6159   -2.7647    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8826   -2.3866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1886   -2.8326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5447   -2.4545    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3875   -2.4727    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9036   -3.1164    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.7273   -3.1635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1799   -2.4738    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0036   -2.5209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3746   -3.2578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1982   -3.3049    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9219   -3.9475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2929   -4.6844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1166   -4.7315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4876   -5.4684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3112   -5.5156    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0349   -6.1582    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0983   -3.9004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6456   -4.5901    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8220   -4.5430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4510   -3.8061    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
  6 11  1  0  0  0  0
 11 12  1  0  0  0  0
  9 13  1  0  0  0  0
 14 13  1  1  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 23 25  1  0  0  0  0
 20 26  2  0  0  0  0
 15 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29  8  1  6  0  0  0
 14 29  1  0  0  0  0
M  END


  Mrv1652309062202092D          

 29 32  0  0  1  0            999 V2000
   -1.8544   -4.9946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8936   -4.1705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6269   -3.7925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1995   -3.7245    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4663   -4.1026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2278   -3.6566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9611   -4.0347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6551   -3.5887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6159   -2.7647    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8826   -2.3866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1886   -2.8326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5447   -2.4545    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3875   -2.4727    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9036   -3.1164    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.7273   -3.1635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1799   -2.4738    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0036   -2.5209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3746   -3.2578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1982   -3.3049    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9219   -3.9475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2929   -4.6844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1166   -4.7315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4876   -5.4684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3112   -5.5156    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0349   -6.1582    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0983   -3.9004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6456   -4.5901    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8220   -4.5430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4510   -3.8061    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
  6 11  1  0  0  0  0
 11 12  1  0  0  0  0
  9 13  1  0  0  0  0
 14 13  1  1  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 23 25  1  0  0  0  0
 20 26  2  0  0  0  0
 15 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29  8  1  6  0  0  0
 14 29  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0222340

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)=CCC1=CC2=C(O[C@@H]3[C@@H]2COC2=C(CC=C(C)C)C(O)=CC=C32)C=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C25H28O4/c1-14(2)5-7-16-11-19-20-13-28-24-17(8-6-15(3)4)21(26)10-9-18(24)25(20)29-23(19)12-22(16)27/h5-6,9-12,20,25-27H,7-8,13H2,1-4H3/t20-,25+/m1/s1

> <INCHI_KEY>
SAXBNTXROWQAKX-NLFFAJNJSA-N

> <FORMULA>
C25H28O4

> <MOLECULAR_WEIGHT>
392.495

> <EXACT_MASS>
392.198759382

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
57

> <JCHEM_AVERAGE_POLARIZABILITY>
45.861033650866325

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,10S)-6,13-bis(3-methylbut-2-en-1-yl)-8,17-dioxatetracyclo[8.7.0.0^{2,7}.0^{11,16}]heptadeca-2,4,6,11(16),12,14-hexaene-5,14-diol

> <JCHEM_LOGP>
5.820463339000002

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.596450826923505

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.984314321019236

> <JCHEM_PKA_STRONGEST_BASIC>
-4.592766935800818

> <JCHEM_POLAR_SURFACE_AREA>
58.92

> <JCHEM_REFRACTIVITY>
117.06439999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(1R,10S)-6,13-bis(3-methylbut-2-en-1-yl)-8,17-dioxatetracyclo[8.7.0.0^{2,7}.0^{11,16}]heptadeca-2,4,6,11(16),12,14-hexaene-5,14-diol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-SEP-22         0                                  
HETATM    1  C   UNK     0      -3.462  -9.323   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -3.535  -7.785   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -4.903  -7.079   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.239  -6.952   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.870  -7.658   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.425  -6.826   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.794  -7.531   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.090  -6.699   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.016  -5.161   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.648  -4.455   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.352  -5.287   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -1.017  -4.582   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0       4.457  -4.616   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       5.420  -5.817   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.958  -5.905   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       7.803  -4.618   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       9.340  -4.706   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      10.033  -6.081   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      11.570  -6.169   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       9.188  -7.369   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       9.880  -8.744   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      11.418  -8.832   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      12.110 -10.208   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      13.648 -10.296   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      11.265 -11.495   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       7.650  -7.281   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       6.805  -8.568   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       5.268  -8.480   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       4.575  -7.105   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   11                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   29                                                  
CONECT    9    8   10   13                                                  
CONECT   10    9   11                                                       
CONECT   11   10    6   12                                                  
CONECT   12   11                                                            
CONECT   13    9   14                                                       
CONECT   14   13   15   29                                                  
CONECT   15   14   16   26                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21   26                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23                                                            
CONECT   26   20   15   27                                                  
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28    8   14                                                  
MASTER        0    0    0    0    0    0    0    0   29    0   64    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₅H₂₈O₄

Average Mass

392.4950 Da

Monoisotopic Mass

392.19876 Da

IUPAC Name

(1R,10S)-6,13-bis(3-methylbut-2-en-1-yl)-8,17-dioxatetracyclo[8.7.0.0^{2,7}.0^{11,16}]heptadeca-2,4,6,11(16),12,14-hexaene-5,14-diol

Traditional Name

(1R,10S)-6,13-bis(3-methylbut-2-en-1-yl)-8,17-dioxatetracyclo[8.7.0.0^{2,7}.0^{11,16}]heptadeca-2,4,6,11(16),12,14-hexaene-5,14-diol

CAS Registry Number

Not Available

SMILES

CC(C)=CCC1=CC2=C(O[C@@H]3[C@@H]2COC2=C(CC=C(C)C)C(O)=CC=C32)C=C1O

InChI Identifier

InChI=1S/C25H28O4/c1-14(2)5-7-16-11-19-20-13-28-24-17(8-6-15(3)4)21(26)10-9-18(24)25(20)29-23(19)12-22(16)27/h5-6,9-12,20,25-27H,7-8,13H2,1-4H3/t20-,25+/m1/s1

InChI Key

SAXBNTXROWQAKX-NLFFAJNJSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Erythrina sigmoidea	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

Isoflavanol
Pterocarpan
Isoflavan
Chromane
Benzopyran
1-benzopyran
Benzofuran
Coumaran
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Benzenoid
Ether
Organoheterocyclic compound
Oxacycle
Organooxygen compound
Organic oxygen 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
logP	5.82	ChemAxon
pKa (Strongest Acidic)	8.98	ChemAxon
pKa (Strongest Basic)	-4.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	58.92 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	117.06 m³·mol⁻¹	ChemAxon
Polarizability	45.86 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	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

68896162

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

162954531

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1r,10s)-6,13-bis(3-methylbut-2-en-1-yl)-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-2,4,6,11(16),12,14-hexaene-5,14-diol (NP0222340)

MOL for NP0222340 ((1r,10s)-6,13-bis(3-methylbut-2-en-1-yl)-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-2,4,6,11(16),12,14-hexaene-5,14-diol)

3D MOL for NP0222340 ((1r,10s)-6,13-bis(3-methylbut-2-en-1-yl)-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-2,4,6,11(16),12,14-hexaene-5,14-diol)

3D SDF for NP0222340 ((1r,10s)-6,13-bis(3-methylbut-2-en-1-yl)-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-2,4,6,11(16),12,14-hexaene-5,14-diol)

3D-SDF for NP0222340 ((1r,10s)-6,13-bis(3-methylbut-2-en-1-yl)-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-2,4,6,11(16),12,14-hexaene-5,14-diol)

PDB for NP0222340 ((1r,10s)-6,13-bis(3-methylbut-2-en-1-yl)-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-2,4,6,11(16),12,14-hexaene-5,14-diol)

3D PDB for NP0222340 ((1r,10s)-6,13-bis(3-methylbut-2-en-1-yl)-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-2,4,6,11(16),12,14-hexaene-5,14-diol)

SMILES for NP0222340 ((1r,10s)-6,13-bis(3-methylbut-2-en-1-yl)-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-2,4,6,11(16),12,14-hexaene-5,14-diol)

INCHI for NP0222340 ((1r,10s)-6,13-bis(3-methylbut-2-en-1-yl)-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-2,4,6,11(16),12,14-hexaene-5,14-diol)

Structure for NP0222340 ((1r,10s)-6,13-bis(3-methylbut-2-en-1-yl)-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-2,4,6,11(16),12,14-hexaene-5,14-diol)

3D Structure for NP0222340 ((1r,10s)-6,13-bis(3-methylbut-2-en-1-yl)-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-2,4,6,11(16),12,14-hexaene-5,14-diol)