NP-MRD: Showing NP-Card for Usambarin C (NP0331584)

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Record Information

Version

2.0

Created at

2023-04-15 00:14:52 UTC

Updated at

2024-09-03 04:16:11 UTC

NP-MRD ID

NP0331584

Natural Product DOI

https://doi.org/10.57994/0564

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Usambarin C

Description

Based on a literature review very few articles have been published on Usambarin C.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652304152302142D          

 26 30  0  0  0  0            999 V2000
   -4.9418    0.7433    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1349    0.5718    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8799   -0.2129    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4319   -0.8259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1770   -1.6106    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3700   -1.7821    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8180   -1.1690    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0110   -1.3405    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3436   -0.8556    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6762   -1.3405    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9311   -2.1251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3791   -2.7382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4279   -2.5667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9799   -3.1798    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6828   -1.7821    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1308   -1.1690    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3858   -0.3844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1927   -0.2129    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7448   -0.8259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2527   -0.1758    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4732   -1.2133    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4898   -1.6106    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7561   -2.1251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3081   -2.7382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1151   -2.5667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0729   -0.3844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
 15 16  2  0  0  0  0
 10 16  1  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
 19 20  1  0  0  0  0
 19 21  1  0  0  0  0
 19 22  1  0  0  0  0
 15 22  1  0  0  0  0
  8 23  2  0  0  0  0
 11 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
  6 25  1  0  0  0  0
  7 26  2  0  0  0  0
  3 26  1  0  0  0  0
M  END


  Mrv1652304152302142D          

 26 30  0  0  0  0            999 V2000
   -4.9418    0.7433    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1349    0.5718    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8799   -0.2129    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4319   -0.8259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1770   -1.6106    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3700   -1.7821    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8180   -1.1690    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0110   -1.3405    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3436   -0.8556    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6762   -1.3405    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9311   -2.1251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3791   -2.7382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4279   -2.5667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9799   -3.1798    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6828   -1.7821    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1308   -1.1690    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3858   -0.3844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1927   -0.2129    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7448   -0.8259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2527   -0.1758    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4732   -1.2133    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4898   -1.6106    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7561   -2.1251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3081   -2.7382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1151   -2.5667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0729   -0.3844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
 15 16  2  0  0  0  0
 10 16  1  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
 19 20  1  0  0  0  0
 19 21  1  0  0  0  0
 19 22  1  0  0  0  0
 15 22  1  0  0  0  0
  8 23  2  0  0  0  0
 11 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
  6 25  1  0  0  0  0
  7 26  2  0  0  0  0
  3 26  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0331584

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC=C2C=CC3=C(OC4=C3C=C(O)C3=C4C=CC(C)(C)O3)C2=C1

> <INCHI_IDENTIFIER>
InChI=1S/C22H18O4/c1-22(2)9-8-15-20-17(11-18(23)21(15)26-22)14-7-5-12-4-6-13(24-3)10-16(12)19(14)25-20/h4-11,23H,1-3H3

> <INCHI_KEY>
UXDGHIQFVMIAPM-UHFFFAOYSA-N

> <FORMULA>
C22H18O4

> <MOLECULAR_WEIGHT>
346.382

> <EXACT_MASS>
346.12050906

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
44

> <JCHEM_AVERAGE_POLARIZABILITY>
38.683513722723326

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
16-methoxy-7,7-dimethyl-6,12-dioxapentacyclo[11.8.0.0^{2,11}.0^{5,10}.0^{14,19}]henicosa-1(13),2(11),3,5(10),8,14,16,18,20-nonaen-4-ol

> <JCHEM_LOGP>
4.580110668333333

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.887786124227713

> <JCHEM_PKA_STRONGEST_BASIC>
-2.94173628917125

> <JCHEM_POLAR_SURFACE_AREA>
51.83

> <JCHEM_REFRACTIVITY>
100.51450000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
16-methoxy-7,7-dimethyl-6,12-dioxapentacyclo[11.8.0.0^{2,11}.0^{5,10}.0^{14,19}]henicosa-1(13),2(11),3,5(10),8,14,16,18,20-nonaen-4-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  C   UNK     0      -9.225   1.387   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -7.718   1.067   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -7.243  -0.397   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -8.273  -1.542   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -7.797  -3.006   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -6.291  -3.327   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -5.260  -2.182   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -3.754  -2.502   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -2.508  -1.597   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      -1.262  -2.502   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.738  -3.967   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.708  -5.111   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.799  -4.791   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       1.829  -5.936   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       1.275  -3.327   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.244  -2.182   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.720  -0.718   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.226  -0.397   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.257  -1.542   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.205  -0.328   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.617  -2.265   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       2.781  -3.006   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      -3.278  -3.967   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -4.309  -5.111   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -5.815  -4.791   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -5.736  -0.718   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   26                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   25                                                  
CONECT    7    6    8   26                                                  
CONECT    8    7    9   23                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   16                                                  
CONECT   11   10   12   23                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16   22                                                  
CONECT   16   15   10   17                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   21   22                                             
CONECT   20   19                                                            
CONECT   21   19                                                            
CONECT   22   19   15                                                       
CONECT   23    8   11   24                                                  
CONECT   24   23   25                                                       
CONECT   25   24    6                                                       
CONECT   26    7    3                                                       
MASTER        0    0    0    0    0    0    0    0   26    0   60    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₂H₁₈O₄

Average Mass

346.3820 Da

Monoisotopic Mass

346.12051 Da

IUPAC Name

16-methoxy-7,7-dimethyl-6,12-dioxapentacyclo[11.8.0.0^{2,11}.0^{5,10}.0^{14,19}]henicosa-1(13),2(11),3,5(10),8,14,16,18,20-nonaen-4-ol

Traditional Name

16-methoxy-7,7-dimethyl-6,12-dioxapentacyclo[11.8.0.0^{2,11}.0^{5,10}.0^{14,19}]henicosa-1(13),2(11),3,5(10),8,14,16,18,20-nonaen-4-ol

CAS Registry Number

Not Available

SMILES

COC1=CC=C2C=CC3=C(OC4=C3C=C(O)C3=C4C=CC(C)(C)O3)C2=C1

InChI Identifier

InChI=1S/C22H18O4/c1-22(2)9-8-15-20-17(11-18(23)21(15)26-22)14-7-5-12-4-6-13(24-3)10-16(12)19(14)25-20/h4-11,23H,1-3H3

InChI Key

UXDGHIQFVMIAPM-UHFFFAOYSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
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
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
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
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

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

Chemical Taxonomy

Classification

Not classified

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	4.58	ChemAxon
pKa (Strongest Acidic)	8.89	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	1	ChemAxon
Refractivity	100.51 m³·mol⁻¹	ChemAxon
Polarizability	38.68 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for Usambarin C (NP0331584)

MOL for NP0331584 (Usambarin C)

3D MOL for NP0331584 (Usambarin C)

3D SDF for NP0331584 (Usambarin C)

3D-SDF for NP0331584 (Usambarin C)

PDB for NP0331584 (Usambarin C)

3D PDB for NP0331584 (Usambarin C)

SMILES for NP0331584 (Usambarin C)

INCHI for NP0331584 (Usambarin C)

Structure for NP0331584 (Usambarin C)

3D Structure for NP0331584 (Usambarin C)