Anacardicin - Compound Card

Anacardicin

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Anacardicin

Structure
Zoomed Structure
  • Family: Anacardiaceae
  • Kingdom: Plantae
  • Class: Lignan
Canonical Smiles COc1cc(cc(c1CCc1c(OC)cc(cc1OC)C(=O)OC)OC)C(=O)OC
InChI InChI=1S/C22H26O8/c1-25-17-9-13(21(23)29-5)10-18(26-2)15(17)7-8-16-19(27-3)11-14(22(24)30-6)12-20(16)28-4/h9-12H,7-8H2,1-6H3
InChIKey BANZFRHVOVHPCX-UHFFFAOYSA-N
Formula C22H26O8
HBA 8
HBD 0
MW 418.44
Rotatable Bonds 9
TPSA 89.52
LogP 3.08
Number Rings 2
Number Aromatic Rings 2
Heavy Atom Count 30
Formal Charge 0
Fraction CSP3 0.36
Exact Mass 418.16
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Anacardium occidentale Anacardiaceae Plantae 171929

Showing of synonyms

  • Taiwo Bamigboye J, Fatokun Amos A, et al. (2017). Identification of compounds with cytotoxic activity from the leaf of the Nigerian medicinal plant, Anacardium occidentale L. (Anacardiaceae). Bioorganic & Medicinal Chemistry, 2017, 25(8), 2327-2335. [View]
Pubchem: 132961494

No compound-protein relationship available.

Structure

SMILES: c1ccccc1CCc2ccccc2

Level: 1

Mol. Weight: 182.27 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 78.11 g/mol

Cytotoxic

Absorption

Caco-2 (logPapp)
-4.31
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.670
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-3.3

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.610
Plasma Protein Binding
18.69
Steady State Volume of Distribution
-

Metabolism

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

Excretion

Clearance
3.800
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
1.690
Biodegradation
Toxic
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
0.820
Liver Injury II
Safe
hERG Blockers
Safe
Daphnia Maga
6.840
Micronucleos
Safe
NR-AhR
Safe
NR-AR
Safe
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
-18.080
Rat (Acute)
2.530
Rat (Chronic Oral)
2.890
Fathead Minnow
5.270
Respiratory Disease
Safe
Skin Sensitisation
Safe
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
436.110
Hydration Free Energy
-5.660
Log(D) at pH=7.4
5.760
Log(P)
5.53
Log S
-4.51
Log(Vapor Pressure)
-7.0
Melting Point
113.23
pKa Acid
10.68
pKa Basic
1.19
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.9510
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.9190
Thymidylate synthase P0A886 TYSY_ECO57 Escherichia coli O157:H7 3 0.9179
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 4 0.8998
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8880
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.8794
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8602
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8594
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8152
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.8037
Serine/threonine-protein kinase 10 O94804 STK10_HUMAN Homo sapiens 3 0.8034
Cytochrome P450 1A1 P04798 CP1A1_HUMAN Homo sapiens 3 0.7938
Peroxisome proliferator-activated receptor gamma P37231 PPARG_HUMAN Homo sapiens 3 0.7783
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7738
UDP-N-acetylmuramoyl-tripeptide--D-alanyl-D-alanine ligase Q8DNV6 Q8DNV6_STRR6 Streptococcus pneumoniae 3 0.7567
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 2 0.7509
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7492
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7428
Tau-tubulin kinase 1 Q5TCY1 TTBK1_HUMAN Homo sapiens 3 0.7427
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 2 0.7423
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 2 0.7396
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7378
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7366
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7365
Gag-Pol polyprotein P03367 POL_HV1BR Human immunodeficiency virus type 1 group M subtype B 3 0.7350
RNA-dependent RNA polymerase Q6A562 Q6A562_9VIRU Thosea asigna virus 2 0.7343
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7330
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7321
Gag-Pol polyprotein P04584 POL_HV2RO Human immunodeficiency virus type 2 subtype A 4 0.7312
Thymidylate synthase P45352 TYSY_RAT Rattus norvegicus 2 0.7261
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7249
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 2 0.7230
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7227
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7223
L-lactate dehydrogenase A chain P13491 LDHA_RABIT Oryctolagus cuniculus 2 0.7206
Protoporphyrinogen oxidase P50336 PPOX_HUMAN Homo sapiens 3 0.7201
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 2 0.7194
HTH-type transcriptional regulator TtgR Q9AIU0 TTGR_PSEPT Pseudomonas putida 3 0.7190
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7184
Metallo-beta-lactamase type 2 P26918 BLAB_AERHY Aeromonas hydrophila 2 0.7181
Caspase-3 P42574 CASP3_HUMAN Homo sapiens 2 0.7163
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7161
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 2 0.7147
Serine/threonine-protein kinase Chk2 O96017 CHK2_HUMAN Homo sapiens 3 0.7137
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7128
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 2 0.7122
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.7119
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 2 0.7119
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 3 0.7114
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7101
IOMT 3 Q06YR3 Q06YR3_MEDTR Medicago truncatula 3 0.7097
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.7093
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7091
Cytosolic purine 5'-nucleotidase P49902 5NTC_HUMAN Homo sapiens 2 0.7090
17beta-hydroxysteroid dehydrogenase O93874 O93874_COCLU Cochliobolus lunatus 2 0.7062
NADPH dehydrogenase 1 Q02899 OYE1_SACPS Saccharomyces pastorianus 2 0.7056
NAD(P)H dehydrogenase [quinone] 1 P15559 NQO1_HUMAN Homo sapiens 4 0.7047
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 2 0.7039
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 2 0.7038
5-methylthioadenosine/S-adenosylhomocysteine deaminase Q7NZ90 Q7NZ90_CHRVO Chromobacterium violaceum 2 0.7016
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 2 0.7011
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7004

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