NP-MRD: Showing NP-Card for 3,4-dihydroxy-2-[(2e,6e,10e)-3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraen-1-yl]phenyl acetate (NP0188993)

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Record Information

Version

2.0

Created at

2022-09-04 05:24:54 UTC

Updated at

2022-09-04 05:24:54 UTC

NP-MRD ID

NP0188993

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3,4-dihydroxy-2-[(2e,6e,10e)-3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraen-1-yl]phenyl acetate

Description

Suillin belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units. 3,4-dihydroxy-2-[(2e,6e,10e)-3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraen-1-yl]phenyl acetate is found in Suillus granulatus, Suillus placidus and Suillus variegatus. 3,4-dihydroxy-2-[(2e,6e,10e)-3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraen-1-yl]phenyl acetate was first documented in 2014 (PMID: 24606477). Based on a literature review a small amount of articles have been published on Suillin (PMID: 35576219) (PMID: 34217708) (PMID: 28013555) (PMID: 27174331).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309042207242D          

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M  END

     RDKit          3D

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M  END


  Mrv1652309042207242D          

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M  END
> <DATABASE_ID>
NP0188993

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)=CCC\C(C)=C\CC\C(C)=C\CC\C(C)=C\CC1=C(O)C(O)=CC=C1OC(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C28H40O4/c1-20(2)10-7-11-21(3)12-8-13-22(4)14-9-15-23(5)16-17-25-27(32-24(6)29)19-18-26(30)28(25)31/h10,12,14,16,18-19,30-31H,7-9,11,13,15,17H2,1-6H3/b21-12+,22-14+,23-16+

> <INCHI_KEY>
TVYGOMSIBBSIKO-MLAGYPMBSA-N

> <FORMULA>
C28H40O4

> <MOLECULAR_WEIGHT>
440.624

> <EXACT_MASS>
440.292659768

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
72

> <JCHEM_AVERAGE_POLARIZABILITY>
52.87049172946172

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3,4-dihydroxy-2-[(2E,6E,10E)-3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraen-1-yl]phenyl acetate

> <JCHEM_LOGP>
7.681085971333334

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.413088158373391

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.816965993671994

> <JCHEM_PKA_STRONGEST_BASIC>
-6.257315104011771

> <JCHEM_POLAR_SURFACE_AREA>
66.76

> <JCHEM_REFRACTIVITY>
136.80280000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
13

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
3,4-dihydroxy-2-[(2E,6E,10E)-3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraen-1-yl]phenyl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-22         0                                  
HETATM    1  C   UNK     0       2.667   6.160   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       4.001   3.850   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -1.334  -0.770   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -2.667   1.540   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -4.001   2.310   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -4.001   3.850   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -5.335   1.540   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -6.668   2.310   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -8.002   1.540   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -9.336   2.310   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -9.336   3.850   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0     -10.669   1.540   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0     -12.003   2.310   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0     -13.337   1.540   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0     -14.670   2.310   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0     -14.670   3.850   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0     -16.004   1.540   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0     -17.338   2.310   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0     -18.672   1.540   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0     -20.005   2.310   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0     -21.339   1.540   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0     -20.005   3.850   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   12                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10    5   13                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30                                                            
MASTER        0    0    0    0    0    0    0    0   32    0   64    0
END

View in JSmol

Synonyms

Value	Source
4-Acetoxy-3-geranylgeranyl-1,2-dihydroxybenzene	MeSH

Chemical Formula

C₂₈H₄₀O₄

Average Mass

440.6240 Da

Monoisotopic Mass

440.29266 Da

IUPAC Name

3,4-dihydroxy-2-[(2E,6E,10E)-3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraen-1-yl]phenyl acetate

Traditional Name

3,4-dihydroxy-2-[(2E,6E,10E)-3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraen-1-yl]phenyl acetate

CAS Registry Number

Not Available

SMILES

CC(C)=CCC\C(C)=C\CC\C(C)=C\CC\C(C)=C\CC1=C(O)C(O)=CC=C1OC(C)=O

InChI Identifier

InChI=1S/C28H40O4/c1-20(2)10-7-11-21(3)12-8-13-22(4)14-9-15-23(5)16-17-25-27(32-24(6)29)19-18-26(30)28(25)31/h10,12,14,16,18-19,30-31H,7-9,11,13,15,17H2,1-6H3/b21-12+,22-14+,23-16+

InChI Key

TVYGOMSIBBSIKO-MLAGYPMBSA-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
Suillus granulatus	LOTUS Database	35616633
Suillus placidus	LOTUS Database	35616633
Suillus variegatus	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Diterpenoids

Alternative Parents

Substituents

Diterpenoid
Phenol ester
Phenoxy compound
Catechol
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Monocyclic benzene moiety
Benzenoid
Carboxylic acid ester
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Hydrocarbon derivative
Organic oxide
Carbonyl group
Organic oxygen compound
Organooxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic 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	7.68	ChemAxon
pKa (Strongest Acidic)	8.82	ChemAxon
pKa (Strongest Basic)	-6.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	66.76 Å²	ChemAxon
Rotatable Bond Count	13	ChemAxon
Refractivity	136.8 m³·mol⁻¹	ChemAxon
Polarizability	52.87 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	No	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

C00057747

Chemspider ID

4534053

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5387599

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Andrade JM, Pachar P, Trujillo L, Cartuche L: Suillin: A mixed-type acetylcholinesterase inhibitor from Suillus luteus which is used by Saraguros indigenous, southern Ecuador. PLoS One. 2022 May 16;17(5):e0268292. doi: 10.1371/journal.pone.0268292. eCollection 2022. [PubMed:35576219 ]
Yan Y, Yao S, Jia Z, Zhao J, Wang L: Iso-suillin-induced DNA damage leading to cell cycle arrest and apoptosis arised from p53 phosphorylation in A549 cells. Eur J Pharmacol. 2021 Sep 15;907:174299. doi: 10.1016/j.ejphar.2021.174299. Epub 2021 Jul 1. [PubMed:34217708 ]
Venditti A, Frezza C, Sciubba F, Serafini M, Bianco A: Primary and secondary metabolites of an European edible mushroom and its nutraceutical value: Suillus bellinii (Inzenga) Kuntze. Nat Prod Res. 2017 Aug;31(16):1910-1919. doi: 10.1080/14786419.2016.1267731. Epub 2016 Dec 26. [PubMed:28013555 ]
Zhao JX, Zhang QS, Chen Y, Yao SJ, Yan YX, Wang Y, Zhang JX, Wang LA: Iso-suillin from Suillus flavus Induces Apoptosis in Human Small Cell Lung Cancer H446 Cell Line. Chin Med J (Engl). 2016 May 20;129(10):1215-23. doi: 10.4103/0366-6999.181961. [PubMed:27174331 ]
Jia ZQ, Chen Y, Yan YX, Zhao JX: Iso-suillin isolated from Suillus luteus, induces G1 phase arrest and apoptosis in human hepatoma SMMC-7721 cells. Asian Pac J Cancer Prev. 2014;15(3):1423-8. doi: 10.7314/apjcp.2014.15.3.1423. [PubMed:24606477 ]
LOTUS database [Link]

Showing NP-Card for 3,4-dihydroxy-2-[(2e,6e,10e)-3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraen-1-yl]phenyl acetate (NP0188993)

MOL for NP0188993 (3,4-dihydroxy-2-[(2e,6e,10e)-3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraen-1-yl]phenyl acetate)

3D MOL for NP0188993 (3,4-dihydroxy-2-[(2e,6e,10e)-3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraen-1-yl]phenyl acetate)

3D SDF for NP0188993 (3,4-dihydroxy-2-[(2e,6e,10e)-3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraen-1-yl]phenyl acetate)

3D-SDF for NP0188993 (3,4-dihydroxy-2-[(2e,6e,10e)-3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraen-1-yl]phenyl acetate)

PDB for NP0188993 (3,4-dihydroxy-2-[(2e,6e,10e)-3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraen-1-yl]phenyl acetate)

3D PDB for NP0188993 (3,4-dihydroxy-2-[(2e,6e,10e)-3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraen-1-yl]phenyl acetate)

SMILES for NP0188993 (3,4-dihydroxy-2-[(2e,6e,10e)-3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraen-1-yl]phenyl acetate)

INCHI for NP0188993 (3,4-dihydroxy-2-[(2e,6e,10e)-3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraen-1-yl]phenyl acetate)

Structure for NP0188993 (3,4-dihydroxy-2-[(2e,6e,10e)-3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraen-1-yl]phenyl acetate)

3D Structure for NP0188993 (3,4-dihydroxy-2-[(2e,6e,10e)-3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraen-1-yl]phenyl acetate)