1,5-di-O-caffeoylquinic acid - Compound Card

1,5-di-O-caffeoylquinic acid

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1,5-di-O-caffeoylquinic acid

Structure
Zoomed Structure
  • Family: Plantae - Cannabaceae
  • Kingdom: Plantae
  • Class: Phenolic
    • Subclass: Hydroxycinnamic Acid
Canonical Smiles O=C1CC[C@@H]2[C@]([C@H]1C)(C)CC[C@H]1[C@@]2(C)CC[C@@]2([C@]1(C)CC[C@@]1([C@H]2CC(C)(C)CC1)C)C
InChI InChI=1S/C30H50O/c1-20-21(31)9-10-22-27(20,5)12-11-23-28(22,6)16-18-30(8)24-19-25(2,3)13-14-26(24,4)15-17-29(23,30)7/h20,22-24H,9-19H2,1-8H3/t20-,22+,23-,24+,26+,27+,28-,29+,30-/m0/s1
InChIKey OFMXGFHWLZPCFL-SVRPQWSVSA-N
Formula C30H50O
HBA 1
HBD 0
MW 426.73
Rotatable Bonds 0
TPSA 17.07
LogP 8.46
Number Rings 5
Number Aromatic Rings 0
Heavy Atom Count 31
Formal Charge 0
Fraction CSP3 0.97
Exact Mass 426.39
Number of Lipinski Rule Violations 1
# Species Family Kingdom NCBI Taxonomy ID
1 Inula crithmoides Asteraceae Plantae 119182
2 Inula crithmoides Asteraceae Plantae 119182
3 Garcinia edulis Clusiaceae-Guttiferae Plantae 58227
4 Vernonia auriculifera Asteraceae Plantae 3032568
5 Vernonia auriculifera Asteraceae Plantae 3032568
6 Antidesma venosum Euphorbiaceae Plantae 992644
7 Drypetes gerrardii Euphorbiaceae Plantae 992685
8 Drypetes armoracia Euphorbiaceae Plantae 3703
9 Alchornea cordifolia Euphorbiaceae Plantae 316697
10 Citrus aurantium Rutaceae Plantae 43166
11 Paullinia pinnata Sapindaceae Plantae 290984
12 Celtis africana Cannabaceae Plantae 266494

Showing of synonyms

  • Magadula JJ. (2010). A bioactive isoprenylated xanthone and other constituents of Garcinia edulis. Fitoterapia,2010,81(5),420-423. [View] [PubMed]
  • Mahmoud ZF, Salam NAA, et al. (1981). A carotane derivative and a eudesmanolide from Inula crithmoides. Phytochemistry,1981,20(4),735-738. [View]
  • Magadula JJ, Mwangomo DT, et al. (2013). A novel gama-lactone and other constituents of a Tanzanian Antidesma venosum. Spatula DD,2013,3(1),7-12. [View] [PubMed]
  • Siwe-Noundou X, Musyoka TM, et al. (2019). Anti-HIV-1 integrase potency of methylgallate from Alchornea cordifolia using in vitro and in silico approaches.. Scientific reports,2019, 9(1), 4718. [View] [PubMed]
  • Kudzanai IT, Evonia KN, et al. (2020). Antibacterial activity and gas chromatography mass spectrometry (GC–MS)-based metabolite profiles of Celtis africana and its endophytic extracts. Industrial Crops and Products, 2020,157, 112933. [View]
  • Lunga PK, Qin XJ, et al. (2014). Antimicrobial steroidal saponin and oleanane-type triterpenoid saponins from Paullinia pinnata.. BMC complementary and alternative medicine,2014, 14, 369. [View] [PubMed]
  • Bissim S, Kenmogne S, et al. (2019). Bioactive acridone alkaloids and their derivatives from Citrus aurantium (Rutaceae). Phytochemistry Letters, 2019, 29, 148-153. [View]
  • Ng’ang’a MM, Chhabra S, et al. (2008). Chemical constituents from the leaves of Drypetes gerrardii. Biochemical Systematics and Ecology,2008,36,320-322. [View] [PubMed]
  • Ela MAA, El-Lakany AM, et al. (2012). New quinic acid derivatives from hepatoprotective Inula crithmoides root extract. Helvetica Chimica Acta,2012,95,61-66. [View]
  • Wandji J, Tillequin F, et al. (2003). Phenolic constituents from Drypetes armoracia.. Phytochemistry,2003, 63(4), 453-456. [View] [PubMed]
  • Kiplimo JJ, Koorbanally NA. (2012). The phytochemistry and biological activity of secondary metabolites from Kenyan Vernonia and Vepris species. PhD Thesis, University of Kwazulu-Natal, South Africa,2012. [View] [PubMed]
  • Kiplimo JJ, Koorbanally NA, et al. (2011). Triterpenoids from Vernonia auriculifera Hiern exhibit antimicrobial activity. African Journal of Pharmacy and Pharmacology,2011,5(8),1150-1156. [View] [PubMed]
Pubchem: 6474640
Nmrshiftdb2: 60025901
Bindingdb: 50455379
CPRiL: 69227
Structure

SMILES: C1CC(=O)CC(CC2)C1C3CCC(C4C23)C5C(CC4)CCCC5

Level: 0

Mol. Weight: 426.73 g/mol

Antimicrobial
Hepatoprotective

Absorption

Caco-2 (logPapp)
-4.75
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.5
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.38

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
2.09
Plasma Protein Binding
89.1
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Inhibitor
CYP 1A2 Inhibitor
Non-Inhibitor
CYP 1A2 Substrate
Substrate
CYP 2C19 Inhibitor
Non-Inhibitor
CYP 2C19 Substrate
Substrate
CYP 2C9 Inhibitor
Non-Inhibitor
CYP 2C9 Substrate
Non-Substrate
CYP 2D6 Inhibitor
Non-Inhibitor
CYP 2D6 Substrate
Non-Substrate
CYP 3A4 Inhibitor
Non-Inhibitor
CYP 3A4 Substrate
Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
11.67
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.66
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
1.64
Liver Injury II
Toxic
hERG Blockers
Toxic
Daphnia Maga
6.09
Micronucleos
Safe
NR-AhR
Safe
NR-AR
Toxic
NR-AR-LBD
Safe
NR-Aromatase
Safe
NR-ER
Safe
NR-ER-LBD
Safe
NR-GR
Safe
NR-PPAR-gamma
Safe
NR-TR
Safe
T. Pyriformis
-32.16
Rat (Acute)
2.11
Rat (Chronic Oral)
1.46
Fathead Minnow
3.92
Respiratory Disease
Safe
Skin Sensitisation
Toxic
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
426.44
Hydration Free Energy
-3.65
Log(D) at pH=7.4
7.5
Log(P)
7.55
Log S
-6.89
Log(Vapor Pressure)
-7.95
Melting Point
249.27
pKa Acid
12.31
pKa Basic
7.57
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8834
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8834
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8778
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8778
Aldo-keto reductase family 1 member C1 Q04828 AK1C1_HUMAN Homo sapiens 3 0.7789
Aldo-keto reductase family 1 member C1 Q04828 AK1C1_HUMAN Homo sapiens 3 0.7789
Rhodopsin P02699 OPSD_BOVIN Bos taurus 3 0.7709
Rhodopsin P02699 OPSD_BOVIN Bos taurus 3 0.7709
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7704
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7704
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7640
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7640
Retinol dehydratase Q26490 Q26490_SPOFR Spodoptera frugiperda 3 0.7361
Retinol dehydratase Q26490 Q26490_SPOFR Spodoptera frugiperda 3 0.7361
Avidin P02701 AVID_CHICK Gallus gallus 2 0.7187
Avidin P02701 AVID_CHICK Gallus gallus 2 0.7187

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