Bovine Metabolome Database: Showing metabocard for 3,4-Dihydroxy-trans-cinnamate (BMDB0003501)

Identification Taxonomy Physical properties Pathways Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-09-30 23:04:56 UTC

Update Date

2020-03-13 16:34:15 UTC

BMDB ID

BMDB0003501

Secondary Accession Numbers

BMDB03501

Metabolite Identification

Common Name

3,4-Dihydroxy-trans-cinnamate

Description

Caffeic acid, also known as caffeate, belongs to the class of organic compounds known as hydroxycinnamic acids. Hydroxycinnamic acids are compounds containing an cinnamic acid where the benzene ring is hydroxylated. Caffeic acid exists as a solid, possibly soluble (in water), and an extremely weak basic (essentially neutral) compound (based on its pKa) molecule. Caffeic acid exists in all living species, ranging from bacteria to humans. Caffeic acid is formally rated as a possible carcinogen (by IARC 2B) and is also a potentially toxic compound.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
3,4-Dihydroxycinnamic acid	ChEBI
Caffeate	ChEBI
Caffeic acid	ChEBI
3,4-Dihydroxycinnamate	Generator
cis-Caffeate	Generator
3,4-Dihydroxybenzeneacrylate	HMDB
3,4-Dihydroxybenzeneacrylic acid	HMDB
Caffeic acid pure	HMDB
Caffeicacid	HMDB
(2Z)-3-(3,4-Dihydroxyphenyl)-2-propenoic acid	HMDB
(Z)-3-(3,4-Dihydroxyphenyl)-2-propenoic acid	HMDB
(Z)-Caffeic acid	HMDB
3-(3,4-Dihydroxyphenyl)-2-propenoic acid	HMDB
3-(3,4-Dihydroxyphenyl)propenoic acid	HMDB
4-(2'-Carboxyvinyl)-1,2-dihydroxybenzene	HMDB
4-(2-Carboxyethenyl)-1,2-dihydroxybenzene	HMDB
4-(2’-carboxyvinyl)-1,2-dihydroxybenzene	HMDB
DHCA	HMDB
Isocaffeic acid	HMDB
cis-3,4-Dihydroxycinnamic acid	HMDB
cis-Caffeic acid	HMDB

Chemical Formula

C₉H₈O₄

Average Molecular Weight

180.1574

Monoisotopic Molecular Weight

180.042258744

IUPAC Name

(2Z)-3-(3,4-dihydroxyphenyl)prop-2-enoic acid

Traditional Name

caffeicacid

CAS Registry Number

501-16-6

SMILES

OC(=O)\C=C/C1=CC(O)=C(O)C=C1

InChI Identifier

InChI=1S/C9H8O4/c10-7-3-1-6(5-8(7)11)2-4-9(12)13/h1-5,10-11H,(H,12,13)/b4-2-

InChI Key

QAIPRVGONGVQAS-RQOWECAXSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as hydroxycinnamic acids. Hydroxycinnamic acids are compounds containing an cinnamic acid where the benzene ring is hydroxylated.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Cinnamic acids and derivatives

Sub Class

Hydroxycinnamic acids and derivatives

Direct Parent

Hydroxycinnamic acids

Alternative Parents

Substituents

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

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

caffeic acid (CHEBI:17395 )

Ontology

Status

Expected but not Quantified

Origin

Not Available

Biofunction

Not Available

Application

Not Available

Cellular locations

Not Available

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	1.35	Not Available

Predicted Properties

Property	Value	Source
logP	1.53	ChemAxon
pKa (Strongest Acidic)	3.14	ChemAxon
pKa (Strongest Basic)	-6.3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	77.76 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	47.02 m³·mol⁻¹	ChemAxon
Polarizability	16.85 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS)	splash10-00di-9341000000-6dc8d392552b88bd4d8c	View in MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS)	splash10-00di-9351000000-50a6f144c73d7ab2794e	View in MoNA
GC-MS	GC-MS Spectrum - GC-MS (3 TMS)	splash10-014i-2793000000-251334452407128b38bd	View in MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-00di-9341000000-6dc8d392552b88bd4d8c	View in MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-00di-9351000000-50a6f144c73d7ab2794e	View in MoNA
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-014i-2793000000-251334452407128b38bd	View in MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-014i-0692000000-32624fa3a157a1f11cef	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-001r-0900000000-c3283a4b6f6f11b66cfb	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positive	splash10-00e9-5039000000-d55c6a31e04536d33b58	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	View in JSpectraViewer
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-03di-0900000000-298c46c83441485d1d70	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-00kr-9800000000-942c1934d3c7c395499e	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-000i-9000000000-e9bdfc2dec7a449ccb11	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative	splash10-004i-0900000000-b07143eccfcbf1caba0c	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative	splash10-000i-0900000000-8f21d50b78f0d9fde98a	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative	splash10-000i-0900000000-4013461a961ebed6fd99	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative	splash10-0019-2900000000-b41600c20a73cd258d40	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative	splash10-001r-8900000000-81ea3878c2912bdddf71	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative	splash10-000i-0900000000-a1680074d0439bcd4c20	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative	splash10-000i-0900000000-096221135a729c5d6aac	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Negative	splash10-0019-0900000000-98893b92962a162b2fb0	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive	splash10-03dr-2900000000-fc2581b0410dd8cb6e71	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Positive	splash10-000i-9200000000-0fd7b8f57372dc8172d5	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive	splash10-03dr-2900000000-454a31169c27631fb00c	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative	splash10-000i-0900000000-eb2466a330b617695c80	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-004i-0900000000-31b407ecba8c8e813fd0	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-000i-0900000000-8f21d50b78f0d9fde98a	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-000i-0900000000-4013461a961ebed6fd99	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0019-2900000000-71ad48cc68ef0b7fe30d	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03di-0900000000-4d70eb21dfd5dcee3360	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-01wr-0900000000-eb4ac130dea5eced36c9	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0100-9800000000-68217b65b3cfbf177196	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-0900000000-28ed8e427213908fdd9f	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-01ti-0900000000-5913f01901b92071e2fc	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-090u-1900000000-2454d377d14f50d8c9b2	View in MoNA
MS	Mass Spectrum (Electron Ionization)	splash10-001i-4900000000-3c93f113512b8284301d	View in MoNA
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 90 MHz, DMSO-d6, experimental)	Not Available	View in JSpectraViewer
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	Not Available	View in JSpectraViewer