Iso-vitexin - Compound Card

Iso-vitexin

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Iso-vitexin

Structure
Zoomed Structure
  • Family: Plantae - Rutaceae
  • Kingdom: Plantae
  • Class: Flavonoid
    • Subclass: Flavonoid Glycoside
Canonical Smiles OC[C@H]1O[C@H]([C@@H]([C@H]([C@@H]1O)O)O)c1c(O)cc2c(c1O)c(=O)cc(o2)c1ccc(cc1)O
InChI InChI=1S/C21H20O10/c22-7-14-17(26)19(28)20(29)21(31-14)16-11(25)6-13-15(18(16)27)10(24)5-12(30-13)8-1-3-9(23)4-2-8/h1-6,14,17,19-23,25-29H,7H2/t14-,17-,19+,20-,21+/m1/s1
InChIKey MYXNWGACZJSMBT-VJXVFPJBSA-N
Formula C21H20O10
HBA 10
HBD 7
MW 432.38
Rotatable Bonds 3
TPSA 181.05
LogP 0.09
Number Rings 4
Number Aromatic Rings 3
Heavy Atom Count 31
Formal Charge 0
Fraction CSP3 0.29
Exact Mass 432.11
Number of Lipinski Rule Violations 1
# Species Family Kingdom NCBI Taxonomy ID
1 Hyphaene thebaica Arecaceae Plantae 115479
2 Bombax malabaricum Bombacaceae Plantae 45325
3 Borago officinalis Boraginaceae Plantae 13363
4 Artemisia herba-alba Asteraceae Plantae 72329
5 Croton zambezicus Euphorbiaceae Plantae 323089
6 Moraea sisyrinchium Iridaceae Plantae 148530
7 Hyparrhenia hirta Poaceae Plantae 42079
8 Ficus exasperata Moraceae Plantae 459060
9 Ficus sansibarica Moraceae Plantae 309319
10 Ficus saussureana Moraceae Plantae 309296
11 Ficus thonningii Moraceae Plantae 309310
12 Gnidia involucrata Thymelaeaceae Plantae 142743
13 Citrus nobilis x Citrus deliciosa Rutaceae Plantae 558547

Showing of synonyms

  • Ferrari J, Terreaux C, et al. (2000). Benzophenone glycosides from Gnidia involucrata. Phytochemistry,2000,54(8),883-889. [View] [PubMed]
  • Zemmouri H, Ammar S, et al. (2014). Chemical composition and antioxidant activity of Borago officinalis L. leaf extract growing in Algeria. Arabian Journal of Chemistry,2014,in press. [View]
  • Wagner H, Horhammer L, et al. (1970). Flavone-C-glykoside in Croton zambezicus. Phytochemistry,1970,9,897-897. [View]
  • Saleh NAM, El-Newumy SI, et al. (1985). Flavonoid glycosides of Artemisia monosperma and A. herba-alba.. Phytochemistry,1985,24(1),201-203. [View]
  • Bouaziz M, Simmonds MS, et al. (2001). Flavonoids from Hyparrhenia hirta Stapf (Poaceae) growing in Tunisia. Biochemical Systematics and Ecology,2001,29(8),849-851. [View] [PubMed]
  • El-Shabrawy MOA Marzouk MM, Kawashty SA, et al. (2013). Flavonoids from Moraea sisyrinchium (L.) Ker Gawl. (Iridaceae) in Egypt. International Conference on Applied Life Sciences (ICALS2013),2013,UAE. September 15-17, 2013. [View]
  • Greenham JR, Grayer RJ, et al. (2007). Intra-and interspecific variations in vacuolar flavonoids among Ficus species from the Budongo Forest, Uganda.. Biochemical systematics and ecology,2007,35(2),81-90. [View] [PubMed]
  • El-Hagrassi AM, Ali MM, et al. (2011). Phytochemical investigation and biological studies of Bombax malabaricum flowers. Natural Product Research,2011,25(2),141-151. [View] [PubMed]
  • El-Hawary S.S, Issa M.Y, et al. (2022). Potential of (Citrus nobilis Lour x Citrus deliciosa Tenora) metabolites on COVID-19 virus main protease supported by in silico analysis. Natural product research, 2022, 36(11), 2843-2847. [View] [PubMed]
  • Eldahshan OA, Ayoub NA, et al. (2008). Potential superoxide anion radical scavenging activity of doum palm (Hyphaene thebaica L.) leaves extract. Records of Natural Products,2008,2(3),83-93. [View]
Pubchem: 162350
Kegg Ligand: C01714
Chebi: 18330
Nmrshiftdb2: 60005880
Metabolights: MTBLC18330
Bindingdb: 50486938
CPRiL: 54729
Structure

SMILES: c1ccccc1-c(cc2=O)oc(c23)ccc(c3)C4CCCCO4

Level: 2

Mol. Weight: 432.38 g/mol

Structure

SMILES: O=c1ccoc(c12)ccc(c2)C3CCCCO3

Level: 1

Mol. Weight: 432.38 g/mol

Structure

SMILES: c1cccc(c12)oc(cc2=O)-c3ccccc3

Level: 1

Mol. Weight: 432.38 g/mol

Structure

SMILES: c1cccc(c12)occc2=O

Level: 0

Mol. Weight: 432.38 g/mol

Structure

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 432.38 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 432.38 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-6.51
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Non-Absorbed
Madin-Darby Canine Kidney
-5.660
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
1.7

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.820
Plasma Protein Binding
83.5
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Non-Inhibitor
CYP 1A2 Inhibitor
Non-Inhibitor
CYP 1A2 Substrate
Non-Substrate
CYP 2C19 Inhibitor
Non-Inhibitor
CYP 2C19 Substrate
Non-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
Non-Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
11.480
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-1.700
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.880
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.400
Micronucleos
Toxic
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
-47.900
Rat (Acute)
2.510
Rat (Chronic Oral)
4.390
Fathead Minnow
3.910
Respiratory Disease
Toxic
Skin Sensitisation
Toxic
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Toxic

General Properties

Boiling Point
623.770
Hydration Free Energy
-6.750
Log(D) at pH=7.4
0.600
Log(P)
1.16
Log S
-3.88
Log(Vapor Pressure)
-13.78
Melting Point
229.94
pKa Acid
4.37
pKa Basic
8.22
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.9492
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.9492
Histone deacetylase 4 P56524 HDAC4_HUMAN Homo sapiens 3 0.9475
Histone deacetylase 4 P56524 HDAC4_HUMAN Homo sapiens 3 0.9475
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.9249
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.9249
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.9141
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.9141
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.8947
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.8947
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.8880
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.8880
Glycogen phosphorylase, muscle form P00489 PYGM_RABIT Oryctolagus cuniculus 3 0.8786
Glycogen phosphorylase, muscle form P00489 PYGM_RABIT Oryctolagus cuniculus 3 0.8786
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 3 0.8757
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 3 0.8757
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8603
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8603
MAP kinase-activated protein kinase 2 P49137 MAPK2_HUMAN Homo sapiens 3 0.8474
MAP kinase-activated protein kinase 2 P49137 MAPK2_HUMAN Homo sapiens 3 0.8474
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 4 0.8431
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 4 0.8431
Genome polyprotein P26663 POLG_HCVBK Hepatitis C virus genotype 1b 3 0.8378
Genome polyprotein P26663 POLG_HCVBK Hepatitis C virus genotype 1b 3 0.8378
Glucan 1,3-beta-glucosidase P29717 EXG1_CANAL Candida albicans 3 0.8246
Glucan 1,3-beta-glucosidase P29717 EXG1_CANAL Candida albicans 3 0.8246
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8235
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8235
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8154
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8154
Squalene synthase P37268 FDFT_HUMAN Homo sapiens 3 0.8145
Squalene synthase P37268 FDFT_HUMAN Homo sapiens 3 0.8145
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8078
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8078
Beta sliding clamp P0A988 DPO3B_ECOLI Escherichia coli 3 0.8057
Beta sliding clamp P0A988 DPO3B_ECOLI Escherichia coli 3 0.8057
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.8009
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.8009
Anthocyanidin 3-O-glucosyltransferase UFGT P51094 UFOG_VITVI Vitis vinifera 4 0.7919
Anthocyanidin 3-O-glucosyltransferase UFGT P51094 UFOG_VITVI Vitis vinifera 4 0.7919
ATP synthase subunit alpha, mitochondrial P19483 ATPA_BOVIN Bos taurus 3 0.7900
ATP synthase subunit alpha, mitochondrial P19483 ATPA_BOVIN Bos taurus 3 0.7900
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7835
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7835
Valacyclovir hydrolase Q86WA6 BPHL_HUMAN Homo sapiens 3 0.7803
Valacyclovir hydrolase Q86WA6 BPHL_HUMAN Homo sapiens 3 0.7803
Cytohesin-2 Q99418 CYH2_HUMAN Homo sapiens 3 0.7696
Cytohesin-2 Q99418 CYH2_HUMAN Homo sapiens 3 0.7696
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 3 0.7675
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 3 0.7675
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.7628
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.7628
S-adenosylmethionine decarboxylase proenzyme P17707 DCAM_HUMAN Homo sapiens 4 0.7587
S-adenosylmethionine decarboxylase proenzyme P17707 DCAM_HUMAN Homo sapiens 4 0.7587
Protein ppBat Q8A8A4 Q8A8A4_BACTN Bacteroides thetaiotaomicron VPI-5482 2 0.7574
Protein ppBat Q8A8A4 Q8A8A4_BACTN Bacteroides thetaiotaomicron VPI-5482 2 0.7574
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform O02697 PK3CG_PIG Sus scrofa 5 0.7552
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform O02697 PK3CG_PIG Sus scrofa 5 0.7552
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7517
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7517
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.7496
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.7496
Alpha-ketoglutarate-dependent dioxygenase FTO Q9C0B1 FTO_HUMAN Homo sapiens 3 0.7403
Alpha-ketoglutarate-dependent dioxygenase FTO Q9C0B1 FTO_HUMAN Homo sapiens 3 0.7403
cGMP-specific 3',5'-cyclic phosphodiesterase O76074 PDE5A_HUMAN Homo sapiens 4 0.7333
cGMP-specific 3',5'-cyclic phosphodiesterase O76074 PDE5A_HUMAN Homo sapiens 4 0.7333
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7220
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7220
Nucleoside 2-deoxyribosyltransferase Q8RLY5 Q8RLY5_LACHE Lactobacillus helveticus 3 0.7192
Nucleoside 2-deoxyribosyltransferase Q8RLY5 Q8RLY5_LACHE Lactobacillus helveticus 3 0.7192
IOMT 3 Q06YR3 Q06YR3_MEDTR Medicago truncatula 3 0.7169
IOMT 3 Q06YR3 Q06YR3_MEDTR Medicago truncatula 3 0.7169
C-1-tetrahydrofolate synthase, cytoplasmic P11586 C1TC_HUMAN Homo sapiens 3 0.7127
C-1-tetrahydrofolate synthase, cytoplasmic P11586 C1TC_HUMAN Homo sapiens 3 0.7127
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7090
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7090
Neuropilin-1 O14786 NRP1_HUMAN Homo sapiens 3 0.7042
Neuropilin-1 O14786 NRP1_HUMAN Homo sapiens 3 0.7042
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7012
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7012

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