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Bipendensin

Family: Plantae - Meliaceae
Kingdom: Plantae
Class: Phenolic
- Subclass: Phenolic Acetal

Canonical Smiles	Oc1cccc2c1[C@@H](O)[C@H]1O[C@H]1C12Oc2cccc3c2c(O1)ccc3
InChI	InChI=1S/C20H14O5/c21-12-7-3-6-11-16(12)17(22)18-19(23-18)20(11)24-13-8-1-4-10-5-2-9-14(25-20)15(10)13/h1-9,17-19,21-22H/t17-,18-,19-/m1/s1
InChIKey	HDSAIJZBOBVWLA-GUDVDZBRSA-N
Formula	C₂₀H₁₄O₅
HBA	5
HBD	2
MW	334.33
Rotatable Bonds	0
TPSA	71.45
LogP	2.98
Number Rings	6
Number Aromatic Rings	3
Heavy Atom Count	25
Formal Charge	0
Fraction CSP3	0.2
Exact Mass	334.08
Number of Lipinski Rule Violations	0

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Entandrophragma congoënse	Meliaceae	Plantae	2590899
2	Entandrophragma congoense	Meliaceae	Plantae	2590899

Showing of synonyms

Happi GM, Kouam SF, et al. (2015). Minor secondary metabolites from the bark of Entandrophragma congoënse (Meliaceae).. Fitoterapia,2015, 102, 35-40. [View] [PubMed]

Pubchem: 9884095

Zinc: ZINC000027648971

Nmrshiftdb2: 80008030

Chembl: CHEMBL153990

No compound-protein relationship available.

SMILES: c1cccc2c1CC(O3)C3C24Oc5c6c(ccc5)cccc6O4

Level: 0

Mol. Weight: 334.33 g/mol

Anti-plasmodial

Absorption

Caco-2 (logPapp): -4.76
Human Oral Bioavailability 20%: Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.220
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -1.84

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Penetrable
Fraction Unbound (Human): 0.890
Plasma Protein Binding: 59.45
Steady State Volume of Distribution: -

Metabolism

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

Excretion

Clearance: 11.230
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Toxic
Avian: Safe
Bee: Toxic
Bioconcentration Factor: 1.890
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Toxic
Eye Corrosion: Safe
Eye Irritation: Toxic
Maximum Tolerated Dose: -0.380
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 6.040
Micronucleos: Toxic
NR-AhR: Toxic
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: -7.650
Rat (Acute): 2.800
Rat (Chronic Oral): 1.780
Fathead Minnow: 4.880
Respiratory Disease: Toxic
Skin Sensitisation: Toxic
SR-ARE: Safe
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Toxic
SR-p53: Safe

General Properties

Boiling Point: 469.930
Hydration Free Energy: -6.450
Log(D) at pH=7.4: 2.980
Log(P): 3.3
Log S: -3.98
Log(Vapor Pressure): -10.03
Melting Point: 161.4
pKa Acid: 6.51
pKa Basic: 0.1

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Thymidylate synthase	P00469	TYSY_LACCA	Lacticaseibacillus casei	3	0.8989
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	3	0.8626
Mycocyclosin synthase	P9WPP7	CP121_MYCTU	Mycobacterium tuberculosis	3	0.8593
Serpin domain-containing protein	H0ZQY2	H0ZQY2_TAEGU	Taeniopygia guttata	3	0.8590
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	3	0.8554
Heat shock protein HSP 90-beta	P08238	HS90B_HUMAN	Homo sapiens	3	0.8473
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	Q05603	COBT_SALTY	Salmonella typhimurium	3	0.8463
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.8448
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.8386
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase	Q9TQS6	DHDH_MACFA	Macaca fascicularis	3	0.8376
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	3	0.8360
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.8358
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	3	0.8152
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.8125
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.8092
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	4	0.8023
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	3	0.7995
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	3	0.7992
Bifunctional dihydrofolate reductase-thymidylate synthase	P13922	DRTS_PLAFK	Plasmodium falciparum	3	0.7960
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7854
Tyrosine-protein kinase JAK2	O60674	JAK2_HUMAN	Homo sapiens	3	0.7833
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7819
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	3	0.7813
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7709
Ephrin type-B receptor 2	P54763	EPHB2_MOUSE	Mus musculus	3	0.7709
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7708
Methionine aminopeptidase 2	P50579	MAP2_HUMAN	Homo sapiens	3	0.7685
Phospholipase A2, major isoenzyme	P00592	PA21B_PIG	Sus scrofa	3	0.7685
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7673
Serine/threonine-protein kinase pim-1	P11309	PIM1_HUMAN	Homo sapiens	4	0.7666
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	3	0.7664
Thymidylate synthase	P0A886	TYSY_ECO57	Escherichia coli O157:H7	3	0.7661
Nodulin-13	P93330	NOD13_MEDTR	Medicago truncatula	3	0.7579
Proton-gated ion channel	Q7NDN8	GLIC_GLOVI	Gloeobacter violaceus	3	0.7550
Glycogen synthase	Q9V2J8	Q9V2J8_PYRAB	Pyrococcus abyssi	3	0.7541
Cyclic dipeptide N-prenyltransferase	D1D8L6	D1D8L6_ASPFM	Neosartorya fumigata	3	0.7516
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial	O44074	O44074_ASCSU	Ascaris suum	4	0.7472
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.7457
Nitric oxide synthase 3	P29474	NOS3_HUMAN	Homo sapiens	3	0.7436
Fibroblast growth factor receptor 2	P21802	FGFR2_HUMAN	Homo sapiens	3	0.7432
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7413
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform	O02697	PK3CG_PIG	Sus scrofa	4	0.7412
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit delta isoform	O35904	PK3CD_MOUSE	Mus musculus	3	0.7408
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7382
Fibroblast growth factor receptor 2	P21802	FGFR2_HUMAN	Homo sapiens	3	0.7368
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	3	0.7339
Type II methyltransferase M.TaqI	P14385	MTTA_THEAQ	Thermus aquaticus	3	0.7332
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7323
Type II methyltransferase M.TaqI	P14385	MTTA_THEAQ	Thermus aquaticus	3	0.7322
FMN-dependent NAD(P)H:quinone oxidoreductase 1	Q9I5F3	AZOR1_PSEAE	Pseudomonas aeruginosa	3	0.7297
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7261
Streptavidin	P22629	SAV_STRAV	Streptomyces avidinii	3	0.7254
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7233
Gag-Pol polyprotein	O12158	POL_HV192	Human immunodeficiency virus type 1 group M subtype C	3	0.7231
Chalcone--flavanone isomerase 1	P28012	CFI1_MEDSA	Medicago sativa	3	0.7227
Interstitial collagenase	P03956	MMP1_HUMAN	Homo sapiens	3	0.7169
Mitogen-activated protein kinase 14	Q16539	MK14_HUMAN	Homo sapiens	3	0.7153
Stromelysin-1	P08254	MMP3_HUMAN	Homo sapiens	3	0.7150
Non-receptor tyrosine-protein kinase TYK2	P29597	TYK2_HUMAN	Homo sapiens	3	0.7127
Norsolorinic acid synthase	Q12053	AFLC_ASPPU	Aspergillus parasiticus	2	0.7120
Focal adhesion kinase 1	Q05397	FAK1_HUMAN	Homo sapiens	3	0.7093
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7070
Albumin	P02768	ALBU_HUMAN	Homo sapiens	3	0.7050
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.7041
Glutathione S-transferase F2	P46422	GSTF2_ARATH	Arabidopsis thaliana	3	0.7037
Caspase-3	P42574	CASP3_HUMAN	Homo sapiens	3	0.7036
[Pyruvate dehydrogenase (acetyl-transferring)] kinase isozyme 2, mitochondrial	Q15119	PDK2_HUMAN	Homo sapiens	3	0.7022
Genome polyprotein	A0EKU1	A0EKU1_9FLAV	Meaban virus	3	0.7013
Carbonic anhydrase 13	Q8N1Q1	CAH13_HUMAN	Homo sapiens	3	0.7007

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