NP-MRD: Showing NP-Card for Usambarin B (NP0331582)

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Record Information

Version

2.0

Created at

2023-04-15 00:08:45 UTC

Updated at

2024-09-03 04:16:11 UTC

NP-MRD ID

NP0331582

Natural Product DOI

https://doi.org/10.57994/0562

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Usambarin B

Description

Usambarin B was first documented in 2023 (PMID: 37043719). Based on a literature review very few articles have been published on Usambarin B.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652304152302082D          

 27 30  0  0  0  0            999 V2000
    5.7317   -0.4795    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0376   -0.0335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3043   -0.4116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6103    0.0344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6495    0.8585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3828    1.2366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4220    2.0606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1552    2.4387    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1944    3.2628    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5004    3.7088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9277    3.6409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0768    0.7906    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8101    1.1687    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5041    0.7227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8779    1.1504    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3618    0.5068    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8144   -0.1829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4434   -0.9198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6198   -0.9670    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1671   -0.2772    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3435   -0.3244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1092    0.3654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2618    1.1022    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1908    1.7920    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0145    1.7448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0855    1.1494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5381    0.4596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  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
  9 11  1  0  0  0  0
  6 12  2  0  0  0  0
  2 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
  5 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
  4 17  1  0  0  0  0
 17 18  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 24  1  0  0  0  0
 24 25  1  0  0  0  0
 23 26  1  0  0  0  0
 26 27  2  0  0  0  0
 20 27  1  0  0  0  0
 16 27  1  0  0  0  0
M  END


  Mrv1652304152302082D          

 27 30  0  0  0  0            999 V2000
    5.7317   -0.4795    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0376   -0.0335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3043   -0.4116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6103    0.0344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6495    0.8585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3828    1.2366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4220    2.0606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1552    2.4387    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1944    3.2628    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5004    3.7088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9277    3.6409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0768    0.7906    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8101    1.1687    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5041    0.7227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8779    1.1504    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3618    0.5068    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8144   -0.1829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4434   -0.9198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6198   -0.9670    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1671   -0.2772    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3435   -0.3244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1092    0.3654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2618    1.1022    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1908    1.7920    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0145    1.7448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0855    1.1494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5381    0.4596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  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
  9 11  1  0  0  0  0
  6 12  2  0  0  0  0
  2 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
  5 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
  4 17  1  0  0  0  0
 17 18  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 24  1  0  0  0  0
 24 25  1  0  0  0  0
 23 26  1  0  0  0  0
 26 27  2  0  0  0  0
 20 27  1  0  0  0  0
 16 27  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0331582

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC=C2C=CC3=C(OC4=C3C=C(O)C(OC)=C4CC=C(C)C)C2=C1

> <INCHI_IDENTIFIER>
InChI=1S/C23H22O4/c1-13(2)5-9-17-22-19(12-20(24)23(17)26-4)16-10-7-14-6-8-15(25-3)11-18(14)21(16)27-22/h5-8,10-12,24H,9H2,1-4H3

> <INCHI_KEY>
LYXFNFBBWIYDLC-UHFFFAOYSA-N

> <FORMULA>
C23H22O4

> <MOLECULAR_WEIGHT>
362.425

> <EXACT_MASS>
362.151809188

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
49

> <JCHEM_AVERAGE_POLARIZABILITY>
40.765533867381215

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4,14-dimethoxy-15-(3-methylbut-2-en-1-yl)-17-oxatetracyclo[8.7.0.0^{2,7}.0^{11,16}]heptadeca-1(10),2,4,6,8,11(16),12,14-octaen-13-ol

> <JCHEM_LOGP>
5.250382999999999

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.936876742741806

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9374591524793927

> <JCHEM_POLAR_SURFACE_AREA>
51.83

> <JCHEM_REFRACTIVITY>
106.8271

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
4,14-dimethoxy-15-(3-methylbut-2-en-1-yl)-17-oxatetracyclo[8.7.0.0^{2,7}.0^{11,16}]heptadeca-1(10),2,4,6,8,11(16),12,14-octaen-13-ol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 15-APR-23   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   15-APR-23         0                                  
HETATM    1  O   UNK     0      10.699  -0.895   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       9.404  -0.063   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.035  -0.768   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.739   0.064   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.812   1.603   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.181   2.308   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.254   3.847   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.623   4.552   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.696   6.091   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.401   6.923   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      11.065   6.796   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       9.477   1.476   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      10.845   2.181   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      12.141   1.349   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       5.372   2.147   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       4.409   0.946   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.254  -0.341   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.561  -1.717   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.024  -1.805   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.179  -0.517   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       0.641  -0.606   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -0.204   0.682   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       0.489   2.057   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      -0.356   3.345   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      -1.894   3.257   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       2.026   2.146   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       2.871   0.858   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   12                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   17                                                  
CONECT    5    4    6   15                                                  
CONECT    6    5    7   12                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9                                                            
CONECT   12    6    2   13                                                  
CONECT   13   12   14                                                       
CONECT   14   13                                                            
CONECT   15    5   16                                                       
CONECT   16   15   17   27                                                  
CONECT   17   16    4   18                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21   27                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24   26                                                  
CONECT   24   23   25                                                       
CONECT   25   24                                                            
CONECT   26   23   27                                                       
CONECT   27   26   20   16                                                  
MASTER        0    0    0    0    0    0    0    0   27    0   60    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₃H₂₂O₄

Average Mass

362.4250 Da

Monoisotopic Mass

362.15181 Da

IUPAC Name

4,14-dimethoxy-15-(3-methylbut-2-en-1-yl)-17-oxatetracyclo[8.7.0.0^{2,7}.0^{11,16}]heptadeca-1(10),2,4,6,8,11(16),12,14-octaen-13-ol

Traditional Name

4,14-dimethoxy-15-(3-methylbut-2-en-1-yl)-17-oxatetracyclo[8.7.0.0^{2,7}.0^{11,16}]heptadeca-1(10),2,4,6,8,11(16),12,14-octaen-13-ol

CAS Registry Number

Not Available

SMILES

COC1=CC=C2C=CC3=C(OC4=C3C=C(O)C(OC)=C4CC=C(C)C)C2=C1

InChI Identifier

InChI=1S/C23H22O4/c1-13(2)5-9-17-22-19(12-20(24)23(17)26-4)16-10-7-14-6-8-15(25-3)11-18(14)21(16)27-22/h5-8,10-12,24H,9H2,1-4H3

InChI Key

LYXFNFBBWIYDLC-UHFFFAOYSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
TOCSY NMR	[¹H, ¹H] NMR Spectrum (2D, 500 MHz, CD3OD, experimental)	mate.erdelyi@kemi.uu.se	Not Available	Not Available	2024-05-11	View Spectrum
NOESY NMR	[¹H, ¹H] NMR Spectrum (2D, 500 MHz, CDCl3, experimental)	mate.erdelyi@kemi.uu.se	Not Available	Not Available	2024-05-11	View Spectrum
HMBC NMR	[¹H, ¹³C] NMR Spectrum (2D, 500 MHz, CD3OD, experimental)	mate.erdelyi@kemi.uu.se	Not Available	Not Available	2024-05-11	View Spectrum
COSY NMR	[¹H, ¹H] NMR Spectrum (2D, 500 MHz, CD3OD, experimental)	mate.erdelyi@kemi.uu.se	Not Available	Not Available	2024-05-11	View Spectrum
HSQC NMR	[¹H, ¹³C] NMR Spectrum (2D, 500 MHz, CD3OD, experimental)	mate.erdelyi@kemi.uu.se	Not Available	Not Available	2024-05-11	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, CD3OD, experimental)	mate.erdelyi@kemi.uu.se	Not Available	Not Available	2024-05-11	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CD3OD, experimental)	mate.erdelyi@kemi.uu.se	Not Available	Not Available	2024-05-11	View Spectrum
HMBC NMR	[¹H, ¹³C] NMR Spectrum (2D, 500 MHz, CDCl3, experimental)	mate.erdelyi@kemi.uu.se	Not Available	Not Available	2023-04-15	View Spectrum
HSQC NMR	[¹H, ¹³C] NMR Spectrum (2D, 500 MHz, CDCl3, experimental)	mate.erdelyi@kemi.uu.se	Not Available	Not Available	2023-04-15	View Spectrum
NOESY NMR	[¹H, ¹H] NMR Spectrum (2D, 500 MHz, CDCl3, experimental)	mate.erdelyi@kemi.uu.se	Not Available	Not Available	2023-04-15	View Spectrum
TOCSY NMR	[¹H, ¹H] NMR Spectrum (2D, 500 MHz, CDCl3, experimental)	mate.erdelyi@kemi.uu.se	Not Available	Not Available	2023-04-15	View Spectrum
COSY NMR	[¹H, ¹H] NMR Spectrum (2D, 500 MHz, CDCl3, experimental)	mate.erdelyi@kemi.uu.se	Not Available	Not Available	2023-04-15	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, CDCl3, experimental)	mate.erdelyi@kemi.uu.se	Not Available	Not Available	2023-04-15	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CDCl3, experimental)	mate.erdelyi@kemi.uu.se	Not Available	Not Available	2023-04-15	View Spectrum
NOESY NMR	[¹H, ¹H] NMR Spectrum (2D, 500 MHz, CDCl3, experimental)	mate.erdelyi@kemi.uu.se	Not Available	Not Available	2023-04-15	View Spectrum
TOCSY NMR	[¹H, ¹H] NMR Spectrum (2D, 500 MHz, CD3OD, experimental)	mate.erdelyi@kemi.uu.se	Not Available	Not Available	2023-04-15	View Spectrum
HMBC NMR	[¹H, ¹³C] NMR Spectrum (2D, 500 MHz, CD3OD, experimental)	mate.erdelyi@kemi.uu.se	Not Available	Not Available	2023-04-15	View Spectrum
HSQC NMR	[¹H, ¹³C] NMR Spectrum (2D, 500 MHz, CD3OD, experimental)	mate.erdelyi@kemi.uu.se	Not Available	Not Available	2023-04-15	View Spectrum
COSY NMR	[¹H, ¹H] NMR Spectrum (2D, 500 MHz, CD3OD, experimental)	mate.erdelyi@kemi.uu.se	Not Available	Not Available	2023-04-15	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, CD3OD, experimental)	mate.erdelyi@kemi.uu.se	Not Available	Not Available	2023-04-15	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CD3OD, experimental)	mate.erdelyi@kemi.uu.se	Not Available	Not Available	2023-04-15	View Spectrum

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
usambarensis		Not Available

Chemical Taxonomy

Description

This compound belongs to the class of organic compounds known as 2-phenylbenzofurans. These are phenylbenzofurans where the benzofuran moiety is conjugated at the 2-position to a phenyl group.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzofurans

Sub Class

Phenylbenzofurans

Direct Parent

2-phenylbenzofurans

Alternative Parents

Substituents

2-phenylbenzofuran
Naphthofuran
Dibenzofuran
Naphthalene
Anisole
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Benzenoid
Heteroaromatic compound
Furan
Dihydrofuran
Oxacycle
Ether
Organic oxygen compound
Hydrocarbon derivative
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	5.25	ChemAxon
pKa (Strongest Acidic)	8.94	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	51.83 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	106.83 m³·mol⁻¹	ChemAxon
Polarizability	40.77 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	Yes	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

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

171355755

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Chepkirui C, Ali Adem F, Rudenko A, Gutlin Y, Ndakala A, Derese S, Orthaber A, Bourgard C, Yenesew A, Erdelyi M: Benzo[b]naphtho[2,1-d]furans and 2-Phenylnaphthalenes from Streblus usambarensis. J Nat Prod. 2023 Apr 28;86(4):1010-1018. doi: 10.1021/acs.jnatprod.3c00051. Epub 2023 Apr 12. [PubMed:37043719 ]

Showing NP-Card for Usambarin B (NP0331582)

MOL for NP0331582 (Usambarin B)

3D MOL for NP0331582 (Usambarin B)

3D SDF for NP0331582 (Usambarin B)

3D-SDF for NP0331582 (Usambarin B)

PDB for NP0331582 (Usambarin B)

3D PDB for NP0331582 (Usambarin B)

SMILES for NP0331582 (Usambarin B)

INCHI for NP0331582 (Usambarin B)

Structure for NP0331582 (Usambarin B)

3D Structure for NP0331582 (Usambarin B)