6,8-diisoprenylaromadendrin - Compound Card

6,8-diisoprenylaromadendrin

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6,8-diisoprenylaromadendrin

Structure
Zoomed Structure
  • Family: Plantae - Euphorbiaceae
  • Kingdom: Plantae
  • Class: Flavonoid
Canonical Smiles CC(=CCc1c2O[C@H](c3ccc(c(c3)O)O)[C@@H](C(=O)c2c(c(c1O)CC=C(C)C)O)O)C
InChI InChI=1S/C25H28O7/c1-12(2)5-8-15-20(28)16(9-6-13(3)4)25-19(21(15)29)22(30)23(31)24(32-25)14-7-10-17(26)18(27)11-14/h5-7,10-11,23-24,26-29,31H,8-9H2,1-4H3/t23-,24-/m1/s1
InChIKey RGBUXOATBSIOSO-DNQXCXABSA-N
Formula C25H28O7
HBA 7
HBD 5
MW 440.49
Rotatable Bonds 5
TPSA 127.45
LogP 4.2
Number Rings 3
Number Aromatic Rings 2
Heavy Atom Count 32
Formal Charge 0
Fraction CSP3 0.32
Exact Mass 440.18
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Macaranga hurifolia Euphorbiaceae Plantae 396461

Showing of synonyms

  • Pagna JI M, Awazi T, et al. (2022). Antibacterial flavonoids from the fruits of Macaranga hurifolia.. Journal of Asian natural products research,2022, 24(11), 1041-1051. [View] [PubMed]

No compound-protein relationship available.

Structure

SMILES: c1cccc(c12)OC(CC2=O)c3ccccc3

Level: 1

Mol. Weight: 440.49 g/mol

Structure

SMILES: c1cccc(c12)OCCC2=O

Level: 0

Mol. Weight: 440.49 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 440.49 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-6.31
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-5.12
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.04

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.93
Plasma Protein Binding
84.82
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
Substrate
CYP 2C9 Inhibitor
Inhibitor
CYP 2C9 Substrate
Substrate
CYP 2D6 Inhibitor
Non-Inhibitor
CYP 2D6 Substrate
Non-Substrate
CYP 3A4 Inhibitor
Non-Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
11.92
Organic Cation Transporter 2
Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.59
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
0.65
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
6.29
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
-42.06
Rat (Acute)
2.34
Rat (Chronic Oral)
3.62
Fathead Minnow
4.94
Respiratory Disease
Toxic
Skin Sensitisation
Toxic
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Toxic

General Properties

Boiling Point
516.72
Hydration Free Energy
-5.24
Log(D) at pH=7.4
2.66
Log(P)
5.24
Log S
-5.02
Log(Vapor Pressure)
-9.36
Melting Point
187.83
pKa Acid
5.67
pKa Basic
6.67
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Histone deacetylase 4 P56524 HDAC4_HUMAN Homo sapiens 3 0.9304
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 3 0.9047
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 3 0.8985
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.8820
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8590
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 3 0.8517
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8328
Peptidyl-prolyl cis-trans isomerase FKBP5 Q13451 FKBP5_HUMAN Homo sapiens 3 0.8310
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8267
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.8243
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 4 0.8209
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 3 0.8156
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 3 0.8138
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 3 0.8121
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.8118
NAD(P)H-hydrate epimerase Q8K4Z3 NNRE_MOUSE Mus musculus 3 0.8110
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.8035
HTH-type transcriptional regulator QacR P0A0N3 QACR_STAAM Staphylococcus aureus 3 0.7944
Proton-gated ion channel Q7NDN8 GLIC_GLOVI Gloeobacter violaceus 3 0.7942
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase P0AF12 MTNN_ECOLI Escherichia coli 3 0.7831
Lysozyme C II P11941 LYSC2_ONCMY Oncorhynchus mykiss 3 0.7822
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 4 0.7814
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.7808
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7797
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 3 0.7699
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.7627
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7615
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7576
Mitogen-activated protein kinase kinase kinase 5 Q99683 M3K5_HUMAN Homo sapiens 3 0.7553
Lethal(3)malignant brain tumor-like protein 1 Q9Y468 LMBL1_HUMAN Homo sapiens 3 0.7517
Ribonuclease J H9CZL7 H9CZL7_DEIRD Deinococcus radiodurans 3 0.7486
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7477
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.7402
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7372
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 3 0.7321
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 3 0.7257
Anthocyanidin 3-O-glucosyltransferase UFGT P51094 UFOG_VITVI Vitis vinifera 4 0.7234
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 4 0.7201
Peptidyl-prolyl cis-trans isomerase FKBP5 Q13451 FKBP5_HUMAN Homo sapiens 3 0.7179
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7174
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 3 0.7156
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7132
Prolyl endopeptidase P23687 PPCE_PIG Sus scrofa 3 0.7098
Polyribonucleotide nucleotidyltransferase A7ZS61 PNP_ECO24 Escherichia coli O139:H28 3 0.7070
5-methyltetrahydropteroyltriglutamate--homocysteine methyltransferase 1 O50008 METE1_ARATH Arabidopsis thaliana 2 0.7047
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7008

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