AFCDB: Sanguiin H6 (FDB000666)

Record Information

Version

1.0

Creation date

2010-04-08 22:04:40 UTC

Update date

2020-02-24 19:10:11 UTC

Primary ID

FDB000666

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Sanguiin H6

Description

Sanguiin H6 belongs to the class of organic compounds known as hydrolyzable tannins. These are tannins with a structure characterized by either of the following models. In model 1, the structure contains galloyl units (in some cases, shikimic acid units) that are linked to diverse polyol carbohydrate-, catechin-, or triterpenoid units. In model 2, contains at least two galloyl units C-C coupled to each other, and do not contain a glycosidically linked catechin unit. Sanguiin H6 is an extremely weak basic (essentially neutral) compound (based on its pKa). Sanguiin H6 has been detected, but not quantified in, red raspberries. This could make sanguiin H6 a potential biomarker for the consumption of these foods.

CAS Number

82978-00-5

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
Not Available	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	3.21 g/L	ALOGPS
logP	4.03	ALOGPS
logP	6.91	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Acidic)	5.89	ChemAxon
pKa (Strongest Basic)	-6.4	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	41	ChemAxon
Hydrogen Donor Count	29	ChemAxon
Polar Surface Area	877.36 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	424.01 m³·mol⁻¹	ChemAxon
Polarizability	162.59 Å³	ChemAxon
Number of Rings	16	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Chemical Formula

C82H54O52

IUPAC name

36-{5-[({7,8,9,12,13,14,28,29,30,33,34,35-dodecahydroxy-4,17,25,38-tetraoxo-3,18,21,24,39-pentaoxaheptacyclo[20.17.0.0²,¹⁹.0⁵,¹⁰.0¹¹,¹⁶.0²⁶,³¹.0³²,³⁷]nonatriaconta-5,7,9,11,13,15,26(31),27,29,32(37),33,35-dodecaen-20-yl}oxy)carbonyl]-2,3-dihydroxyphenoxy}-7,8,9,12,13,14,28,29,30,33,34,35-dodecahydroxy-4,17,25,38-tetraoxo-3,18,21,24,39-pentaoxaheptacyclo[20.17.0.0²,¹⁹.0⁵,¹⁰.0¹¹,¹⁶.0²⁶,³¹.0³²,³⁷]nonatriaconta-5,7,9,11,13,15,26(31),27,29,32(37),33,35-dodecaen-20-yl 3,4,5-trihydroxybenzoate

InChI Identifier

InChI=1S/C82H54O52/c83-23-1-14(2-24(84)45(23)93)71(112)133-81-70-68(130-77(118)20-9-30(90)50(98)57(105)39(20)41-22(79(120)132-70)11-32(92)52(100)59(41)107)65-35(126-81)13-123-74(115)17-6-27(87)53(101)60(108)42(17)43-44(80(121)128-65)66(63(111)62(110)61(43)109)124-33-4-15(3-25(85)46(33)94)72(113)134-82-69-67(129-76(117)19-8-29(89)49(97)56(104)38(19)40-21(78(119)131-69)10-31(91)51(99)58(40)106)64-34(125-82)12-122-73(114)16-5-26(86)47(95)54(102)36(16)37-18(75(116)127-64)7-28(88)48(96)55(37)103/h1-11,34-35,64-65,67-70,81-111H,12-13H2

InChI Key

FFZOOOCGCNFHAQ-UHFFFAOYSA-N

Isomeric SMILES

OC1=CC(=CC(O)=C1O)C(=O)OC1OC2COC(=O)C3=C(C(O)=C(O)C(O)=C3)C3=C(C(OC4=CC(=CC(O)=C4O)C(=O)OC4OC5COC(=O)C6=C(C(O)=C(O)C(O)=C6)C6=C(C=C(O)C(O)=C6O)C(=O)OC5C5OC(=O)C6=CC(O)=C(O)C(O)=C6C6=C(O)C(O)=C(O)C=C6C(=O)OC45)=C(O)C(O)=C3O)C(=O)OC2C2OC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC12

Average Molecular Weight

1871.275

Monoisotopic Molecular Weight

1870.158112072

Classification

Description

Belongs to the class of organic compounds known as hydrolyzable tannins. These are tannins with a structure characterized by either of the following models. In model 1, the structure contains galloyl units (in some cases, shikimic acid units) that are linked to diverse polyol carbohydrate-, catechin-, or triterpenoid units. In model 2, contains at least two galloyl units C-C coupled to each other, and do not contain a glycosidically linked catechin unit.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Tannins

Sub Class

Hydrolyzable tannins

Direct Parent

Hydrolyzable tannins

Alternative Parents

Substituents

Hydrolyzable tannin
Galloyl ester
Gallic acid or derivatives
Dihydroxybenzoic acid
P-hydroxybenzoic acid alkyl ester
M-hydroxybenzoic acid ester
P-hydroxybenzoic acid ester
Diaryl ether
Benzoate ester
Benzenetriol
Benzoic acid or derivatives
Pyrogallol derivative
Phenoxy compound
Phenol ether
Benzoyl
Catechol
1-hydroxy-2-unsubstituted benzenoid
1-hydroxy-4-unsubstituted benzenoid
Phenol
Monocyclic benzene moiety
Benzenoid
Oxane
Monosaccharide
Carboxylic acid ester
Lactone
Polyol
Ether
Organoheterocyclic compound
Carboxylic acid derivative
Oxacycle
Acetal
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

No ontology term

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Not Available
Physical Description	Not Available
Mass Composition	C 52.63%; H 2.91%; O 44.46%	DFC
Melting Point	Not Available
Boiling Point	Not Available
Experimental Water Solubility	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	[a]D +72 (Me2CO)	DFC
Spectroscopic UV Data	Not Available
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Not Available

MS/MS

Type	Description	Splash Key	View
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0uk9-1900000121-c4979907a80785dc232a	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0udi-1900000131-86bb95bdf0afcd24cb14	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0umi-0900000252-feb8d20224d7b6146204	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0gb9-1900000130-01b3b67ee4f29365c7b3	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-016r-0904020111-7119968e46136147cd22	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00ou-0609010413-c85b9f22a96d0a39bec7	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-1400001963-9f6f447894147bd93ae4	2021-09-21	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0i6u-1300000290-787886b6d3b970a8620d	2021-09-21	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-02u1-3600001690-2a6565b871b7890f2110	2021-09-21	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0v4i-0200000691-a301f6e55a758d6e15c1	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0v4r-7800000793-f2d03aa2674a8066d90d	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-014l-0106000962-ad497e24005b0d28be87	2021-09-25	View Spectrum

NMR

Not Available

External Links

ChemSpider ID

23170960

ChEMBL ID

Not Available

KEGG Compound ID

Not Available

Pubchem Compound ID

16181831

Pubchem Substance ID

Not Available

ChEBI ID

Not Available

Phenol-Explorer ID

446

DrugBank ID

Not Available

HMDB ID

HMDB29526

CRC / DFC (Dictionary of Food Compounds) ID

BFL47-N:BFL47-N

EAFUS ID

Not Available

Dr. Duke ID

SANGUIIN-H-6

BIGG ID

Not Available

KNApSAcK ID

Not Available

HET ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

Not Available

SuperScent ID

Not Available

Wikipedia ID

Not Available

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

Food	Content Range	Average	Reference
Food			Reference

Biological Effects and Interactions

Health Effects / Bioactivities

Descriptor	ID	Definition	Reference
anti angiogenic	48422	An agent and endogenous substances that antagonize or inhibit the development of new blood vessels.	DUKE
topoisomerase-II inhibitor	50750	A topoisomerase inhibitor that inhibits DNA topoisomerase (ATP-hydrolysing), EC 5.99.1.3 (topoisomerase II), which catalyses ATP-dependent breakage of both strands of DNA, passage of the unbroken strands through the breaks, and rejoining of the broken strands.	DUKE
topoisomerase-I inhibitor	50276	A topoisomerase inhibitor that inhibits the bacterial enzymes of the DNA topoisomerases, Type I class (EC 5.99.1.2) that catalyze ATP-independent breakage of one of the two strands of DNA, passage of the unbroken strand through the break, and rejoining of the broken strand. These bacterial enzymes reduce the topological stress in the DNA structure by relaxing negatively, but not positively, supercoiled DNA.	DUKE
VEGF inhibitor	35222	A substance that diminishes the rate of a chemical reaction.	DUKE

Enzymes

Not Available

Pathways

Not Available

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

Not Available

Files

MSDS

Not Available

References

Synthesis Reference

Not Available

General Reference

Not Available

Content Reference

— Rothwell JA, Pérez-Jiménez J, Neveu V, Medina-Ramon A, M'Hiri N, Garcia Lobato P, Manach C, Knox K, Eisner R, Wishart D, Scalbert A. (2013) Phenol-Explorer 3.0: a major update of the Phenol-Explorer database to incorporate data on the effects of food processing on polyphenol content. Database, 10.1093/database/bat070.
— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).

Sanguiin H6 (FDB000666)

Structure for FDB000666 (Sanguiin H6)