NP-MRD: Showing NP-Card for Protosappanin F (NP0332151)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2023-11-29 04:17:32 UTC

Updated at

2024-09-03 04:18:10 UTC

NP-MRD ID

NP0332151

Natural Product DOI

https://doi.org/10.57994/1308

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Protosappanin F

Description

Protosappanin F belongs to the class of organic compounds known as cyclohexylphenols. Cyclohexylphenols are compounds containing a cyclohexane lined to a phenol group. Protosappanin F was first documented in 2024 (PMID: 38705264). Based on a literature review very few articles have been published on Protosappanin F.

Structure

MOL SDF PDB SMILES InChI


  Mrv2104 11292304172D          

 22 24  0  0  1  0            999 V2000
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1434    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.2868   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1434   -2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  5  4  1  0  0  0  0
  5  6  1  1  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
  9 11  1  0  0  0  0
 11 12  2  0  0  0  0
  6 12  1  0  0  0  0
 12 13  1  0  0  0  0
  5 14  1  0  0  0  0
 15 14  1  0  0  0  0
 15 16  1  1  0  0  0
 15 17  1  0  0  0  0
 17 18  1  6  0  0  0
 17 19  1  0  0  0  0
 20 19  1  0  0  0  0
  5 20  1  0  0  0  0
 20 21  1  1  0  0  0
 20 22  1  0  0  0  0
  2 22  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0332151

> <DATABASE_NAME>
NP-MRD

> <SMILES>
O[C@@H]1C[C@]2(O)CC(=C)CO[C@@]2(C[C@H]1O)C1=CC=C(O)C=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C16H20O6/c1-9-5-15(21)6-13(19)14(20)7-16(15,22-8-9)11-3-2-10(17)4-12(11)18/h2-4,13-14,17-21H,1,5-8H2/t13-,14-,15-,16+/m1/s1

> <INCHI_KEY>
UEHJUXZNXOJMQU-FPCVCCKLSA-N

> <FORMULA>
C16H20O6

> <MOLECULAR_WEIGHT>
308.33

> <EXACT_MASS>
308.125988364

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
42

> <JCHEM_AVERAGE_POLARIZABILITY>
31.032635220215106

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(4aR,6R,7R,8aS)-8a-(2,4-dihydroxyphenyl)-3-methylidene-octahydro-2H-1-benzopyran-4a,6,7-triol

> <JCHEM_LOGP>
-0.2923356729999997

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
10.487846201382443

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.929109494244424

> <JCHEM_PKA_STRONGEST_BASIC>
-3.190350696048608

> <JCHEM_POLAR_SURFACE_AREA>
110.38000000000001

> <JCHEM_REFRACTIVITY>
78.39869999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(4aR,6R,7R,8aS)-8a-(2,4-dihydroxyphenyl)-3-methylidene-hexahydro-1-benzopyran-4a,6,7-triol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 29-NOV-23   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-NOV-23         0                                  
HETATM    1  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       2.667   0.000   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.001   0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.667   3.080   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       4.001   5.390   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       5.335   3.080   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       6.668   0.770   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       8.002  -0.000   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       8.002  -3.080   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       4.001  -3.850   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   22                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   14   20                                             
CONECT    6    5    7   12                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11    6   13                                                  
CONECT   13   12                                                            
CONECT   14    5   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20                                                       
CONECT   20   19    5   21   22                                             
CONECT   21   20                                                            
CONECT   22   20    2                                                       
MASTER        0    0    0    0    0    0    0    0   22    0   48    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₆H₂₀O₆

Average Mass

308.3300 Da

Monoisotopic Mass

308.12599 Da

IUPAC Name

(4aR,6R,7R,8aS)-8a-(2,4-dihydroxyphenyl)-3-methylidene-octahydro-2H-1-benzopyran-4a,6,7-triol

Traditional Name

(4aR,6R,7R,8aS)-8a-(2,4-dihydroxyphenyl)-3-methylidene-hexahydro-1-benzopyran-4a,6,7-triol

CAS Registry Number

Not Available

SMILES

O[C@@H]1C[C@]2(O)CC(=C)CO[C@@]2(C[C@H]1O)C1=CC=C(O)C=C1O

InChI Identifier

InChI=1S/C16H20O6/c1-9-5-15(21)6-13(19)14(20)7-16(15,22-8-9)11-3-2-10(17)4-12(11)18/h2-4,13-14,17-21H,1,5-8H2/t13-,14-,15-,16+/m1/s1

InChI Key

UEHJUXZNXOJMQU-FPCVCCKLSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, C2D6OS, experimental)	wangxn@sdu.edu.cn	Shandong University	Xiao-Ning Wang	2023-11-29	View Spectrum
DEPT NMR	[¹³C, ¹H] NMR Spectrum (2D, 151 MHz, C2D6OS, experimental)	wangxn@sdu.edu.cn	Shandong University	Xiao-Ning Wang	2023-11-29	View Spectrum
NOESY NMR	[¹H, ¹H] NMR Spectrum (2D, 600 MHz, C2D6OS, experimental)	wangxn@sdu.edu.cn	Shandong University	Xiao-Ning Wang	2023-11-29	View Spectrum
COSY NMR	[¹H, ¹H] NMR Spectrum (2D, 600 MHz, C2D6OS, experimental)	wangxn@sdu.edu.cn	Shandong University	Xiao-Ning Wang	2023-11-29	View Spectrum
HSQC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, C2D6OS, experimental)	wangxn@sdu.edu.cn	Shandong University	Xiao-Ning Wang	2023-11-29	View Spectrum
HMBC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, C2D6OS, experimental)	wangxn@sdu.edu.cn	Shandong University	Xiao-Ning Wang	2023-11-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, C2D6OS, experimental)	wangxn@sdu.edu.cn	Shandong University	Xiao-Ning Wang	2023-11-29	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

Description

This compound belongs to the class of organic compounds known as cyclohexylphenols. These are compounds containing a cyclohexane lined to a phenol group.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Cyclohexylphenols

Direct Parent

Cyclohexylphenols

Alternative Parents

Substituents

Cyclohexylphenol
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Oxane
Tertiary alcohol
Cyclic alcohol
Secondary alcohol
Oxacycle
Organoheterocyclic compound
Ether
Dialkyl ether
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Alcohol
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	-0.29	ChemAxon
pKa (Strongest Acidic)	8.93	ChemAxon
pKa (Strongest Basic)	-3.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	110.38 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	78.4 m³·mol⁻¹	ChemAxon
Polarizability	31.03 Å³	ChemAxon
Number of Rings	3	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

Feng R, Xu JX, Luan XY, Wang XN, Shen T, Ren DM, Wang XL: Chemical constituents with antioxidant activity from the branches and leaves of Hultholia mimosoides. Phytochemistry. 2024 Jul;223:114131. doi: 10.1016/j.phytochem.2024.114131. Epub 2024 May 3. [PubMed:38705264 ]

Showing NP-Card for Protosappanin F (NP0332151)

MOL for NP0332151 (Protosappanin F)

3D MOL for NP0332151 (Protosappanin F)

3D SDF for NP0332151 (Protosappanin F)

3D-SDF for NP0332151 (Protosappanin F)

PDB for NP0332151 (Protosappanin F)

3D PDB for NP0332151 (Protosappanin F)

SMILES for NP0332151 (Protosappanin F)

INCHI for NP0332151 (Protosappanin F)

Structure for NP0332151 (Protosappanin F)

3D Structure for NP0332151 (Protosappanin F)