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Bonducellin

Family: Plantae - Leguminosae/Fabaceae
Kingdom: Plantae
Class: Flavonoid
- Subclass: Homoisoflavonoid

Canonical Smiles	COc1ccc(cc1)/C=C/1\COc2c(C1=O)ccc(c2)O
InChI	InChI=1S/C17H14O4/c1-20-14-5-2-11(3-6-14)8-12-10-21-16-9-13(18)4-7-15(16)17(12)19/h2-9,18H,10H2,1H3/b12-8+
InChIKey	DLQSYZMPSWHYMW-XYOKQWHBSA-N
Formula	C₁₇H₁₄O₄
HBA	4
HBD	1
MW	282.29
Rotatable Bonds	2
TPSA	55.76
LogP	3.06
Number Rings	3
Number Aromatic Rings	2
Heavy Atom Count	21
Formal Charge	0
Fraction CSP3	0.12
Exact Mass	282.09
Number of Lipinski Rule Violations	0

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Caesalpinia welwitschiana	Leguminosae/Fabaceae	Plantae	1387604

Showing of synonyms

Essoung FRE, Mba'ning BM, et al. (2021). Antifeedant and ovicidal activities of a new cassane and other compounds from Caesalpinia welwitschiana Oliv. and Caesalpinia bonduc L. against Tuta absoluta (Lepidoptera: Gelechiidae).. Natural product research,2021, 35(24), 5681-5691. [View] [PubMed]

Pubchem: 14079439

Cas: 83162-84-9

Zinc: ZINC000014454949

Nmrshiftdb2: 60069305

Chembl: CHEMBL450675

Bindingdb: 50443669

CPRiL: 214286

SMILES: c1ccccc1C=C(C2=O)COc(c23)cccc3

Level: 1

Mol. Weight: 282.29 g/mol

SMILES: O=C1C(=C)COc(c12)cccc2

Level: 0

Mol. Weight: 282.29 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 282.29 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -4.69
Human Oral Bioavailability 20%: Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.550
Human Oral Bioavailability 50%: Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -2.41

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Penetrable
Fraction Unbound (Human): 1.240
Plasma Protein Binding: 67.46
Steady State Volume of Distribution: -

Metabolism

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

Excretion

Clearance: 6.350
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: 1.370
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 0.860
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 5.670
Micronucleos: Toxic
NR-AhR: Toxic
NR-AR: Safe
NR-AR-LBD: Safe
NR-Aromatase: Safe
NR-ER: Toxic
NR-ER-LBD: Safe
NR-GR: Safe
NR-PPAR-gamma: Safe
NR-TR: Toxic
T. Pyriformis: 4.670
Rat (Acute): 1.980
Rat (Chronic Oral): 2.420
Fathead Minnow: 4.880
Respiratory Disease: Safe
Skin Sensitisation: Safe
SR-ARE: Toxic
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Toxic
SR-p53: Safe

General Properties

Boiling Point: 411.150
Hydration Free Energy: -8.770
Log(D) at pH=7.4: 3.430
Log(P): 3.25
Log S: -5.65
Log(Vapor Pressure): -6.94
Melting Point: 189.21
pKa Acid: 7.85
pKa Basic: 4.76

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Flavoredoxin	Q72HI0	Q72HI0_THET2	Thermus thermophilus	3	0.9395
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.9334
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.9293
Ribosomal small subunit pseudouridine synthase A	P0AA43	RSUA_ECOLI	Escherichia coli	3	0.9262
Reaction center protein L chain	P0C0Y7	RCEH_RHOSH	Rhodobacter sphaeroides	3	0.9227
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.9148
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.9146
NADPH-dependent 7-cyano-7-deazaguanine reductase	Q9KTK0	QUEF_VIBCH	Vibrio cholerae serotype O1	3	0.9127
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.9017
Urokinase-type plasminogen activator	P00749	UROK_HUMAN	Homo sapiens	3	0.8920
Mitogen-activated protein kinase 8	P45983	MK08_HUMAN	Homo sapiens	3	0.8920
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.8904
Sulfotransferase 1A1	P50225	ST1A1_HUMAN	Homo sapiens	3	0.8829
Pteridine reductase	O76290	O76290_TRYBB	Trypanosoma brucei brucei	3	0.8772
Decaprenylphosphoryl-beta-D-ribose oxidase	I6X8C4	I6X8C4_MYCTU	Mycobacterium tuberculosis	3	0.8700
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.8517
Trichothecene 15-O-acetyltransferase TRI3	Q9C1B7	TRI3_FUSSP	Fusarium sporotrichioides	3	0.8407
HTH-type transcriptional regulator EthR	P9WMC1	ETHR_MYCTU	Mycobacterium tuberculosis	4	0.8399
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.8395
Histone deacetylase 8	Q9BY41	HDAC8_HUMAN	Homo sapiens	3	0.8343
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.8248
Chalcone--flavanone isomerase 1	P28012	CFI1_MEDSA	Medicago sativa	3	0.8156
IOMT 3	Q06YR3	Q06YR3_MEDTR	Medicago truncatula	4	0.8128
Matrilysin	P09237	MMP7_HUMAN	Homo sapiens	3	0.8082
Peroxisome proliferator-activated receptor gamma	P37231	PPARG_HUMAN	Homo sapiens	3	0.8007
HTH-type transcriptional regulator EthR	P9WMC1	ETHR_MYCTU	Mycobacterium tuberculosis	3	0.7934
17beta-hydroxysteroid dehydrogenase	O93874	O93874_COCLU	Cochliobolus lunatus	4	0.7927
Aldo-keto reductase family 1 member C3	P42330	AK1C3_HUMAN	Homo sapiens	2	0.7893
Xylose isomerase	P24300	XYLA_STRRU	Streptomyces rubiginosus	3	0.7890
Toxoflavin degrading enzyme	E3SET7	E3SET7_PAEPO	Paenibacillus polymyxa	3	0.7884
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7851
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7825
S-norcoclaurine synthase	Q67A25	NCS_THLFG	Thalictrum flavum subsp. glaucum	3	0.7794
Dihydrofolate reductase	P00374	DYR_HUMAN	Homo sapiens	3	0.7786
Gag-Pol polyprotein	P03367	POL_HV1BR	Human immunodeficiency virus type 1 group M subtype B	3	0.7781
ALK tyrosine kinase receptor	Q9UM73	ALK_HUMAN	Homo sapiens	3	0.7769
Transthyretin	P02766	TTHY_HUMAN	Homo sapiens	4	0.7708
Dihydrofolate reductase	P00374	DYR_HUMAN	Homo sapiens	3	0.7697
Gag-Pol polyprotein	P04584	POL_HV2RO	Human immunodeficiency virus type 2 subtype A	3	0.7691
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	2	0.7672
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	4	0.7619
Flavin-dependent thymidylate synthase	Q9WYT0	THYX_THEMA	Thermotoga maritima	3	0.7602
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	Q05603	COBT_SALTY	Salmonella typhimurium	2	0.7601
Tannase	B3Y018	B3Y018_LACPN	Lactiplantibacillus plantarum	3	0.7595
LIM domain kinase 1	P53667	LIMK1_HUMAN	Homo sapiens	2	0.7537
Beta-1 adrenergic receptor	P07700	ADRB1_MELGA	Meleagris gallopavo	2	0.7520
Nuclear receptor subfamily 1 group I member 2	O75469	NR1I2_HUMAN	Homo sapiens	3	0.7515
Photosynthetic reaction center cytochrome c subunit	P07173	CYCR_BLAVI	Blastochloris viridis	2	0.7510
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7488
Casein kinase II subunit alpha	P28523	CSK2A_MAIZE	Zea mays	4	0.7475
Thymidylate synthase	P00469	TYSY_LACCA	Lacticaseibacillus casei	3	0.7451
Beta-1 adrenergic receptor	P07700	ADRB1_MELGA	Meleagris gallopavo	2	0.7410
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7389
MAP kinase-activated protein kinase 2	P49137	MAPK2_HUMAN	Homo sapiens	3	0.7386
Putative N-acetyl glucosaminyl transferase	Q6U8B0	Q6U8B0_RAOTE	Raoultella terrigena	3	0.7367
Kynurenine/alpha-aminoadipate aminotransferase, mitochondrial	Q8N5Z0	AADAT_HUMAN	Homo sapiens	2	0.7365
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.7359
APH(2'')-Id	O68183	O68183_ENTCA	Enterococcus casseliflavus	3	0.7346
Mitogen-activated protein kinase kinase kinase 5	Q99683	M3K5_HUMAN	Homo sapiens	3	0.7339
3-hydroxyanthranilate 3,4-dioxygenase	Q1LCS4	3HAO_CUPMC	Cupriavidus metallidurans	2	0.7336
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7323
Pantothenate synthetase	P9WIL4	PANC_MYCTO	Mycobacterium tuberculosis	2	0.7314
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	2	0.7305
Serine/threonine-protein kinase Chk2	O96017	CHK2_HUMAN	Homo sapiens	2	0.7293
NAD(P)H-hydrate epimerase	Q8K4Z3	NNRE_MOUSE	Mus musculus	2	0.7292
Polymerase acidic protein	C3W5S0	C3W5S0_I09A0	Influenza A virus	2	0.7280
Tannase	B3Y018	B3Y018_LACPN	Lactiplantibacillus plantarum	3	0.7270
ATP synthase subunit alpha, mitochondrial	P19483	ATPA_BOVIN	Bos taurus	4	0.7253
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.7247
Phosphodiesterase	Q8WQX9	Q8WQX9_9TRYP	Trypanosoma brucei	3	0.7243
Beta-galactoside-specific lectin 4	Q6ITZ3	ML4_VISAL	Viscum album	2	0.7231
Mitogen-activated protein kinase 8	P45983	MK08_HUMAN	Homo sapiens	3	0.7213
Endoplasmic reticulum aminopeptidase 2	Q6P179	ERAP2_HUMAN	Homo sapiens	2	0.7206
Albumin	P02768	ALBU_HUMAN	Homo sapiens	2	0.7200
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	2	0.7179
Mitochondrial poly(A) polymerase	F1NBW0	F1NBW0_CHICK	Gallus gallus	2	0.7176
2-C-methyl-D-erythritol 2,4-cyclodiphosphate synthase	Q8RQP5	ISPF_THET8	Thermus thermophilus	3	0.7169
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	2	0.7169
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7167
UDP-galactopyranose mutase	Q48485	GLF1_KLEPN	Klebsiella pneumoniae	3	0.7146
Glycogen phosphorylase, liver form	P06737	PYGL_HUMAN	Homo sapiens	3	0.7144
Genome polyprotein	P26663	POLG_HCVBK	Hepatitis C virus genotype 1b	2	0.7140
rRNA N-glycosylase	D9J2T9	D9J2T9_MOMBA	Momordica balsamina	2	0.7140
Genome polyprotein	P26663	POLG_HCVBK	Hepatitis C virus genotype 1b	2	0.7138
Macrophage metalloelastase	P39900	MMP12_HUMAN	Homo sapiens	2	0.7135
DNA gyrase subunit B	Q839Z1	GYRB_ENTFA	Enterococcus faecalis	2	0.7135
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	2	0.7112
2-aminohexano-6-lactam racemase	Q7M181	ACLR_ACHOB	Achromobacter obae	2	0.7103
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	3	0.7101
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	3	0.7090
Pteridine reductase 1	Q01782	PTR1_LEIMA	Leishmania major	3	0.7089
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7084
Mitogen-activated protein kinase 14	Q16539	MK14_HUMAN	Homo sapiens	3	0.7072
Glycogen phosphorylase, liver form	P06737	PYGL_HUMAN	Homo sapiens	3	0.7056
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7048
Serine/threonine-protein kinase PLK1	P53350	PLK1_HUMAN	Homo sapiens	3	0.7044
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.7042
Aldehyde dehydrogenase, mitochondrial	P05091	ALDH2_HUMAN	Homo sapiens	4	0.7030
Acetolactate synthase, chloroplastic	P17597	ILVB_ARATH	Arabidopsis thaliana	2	0.7027
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	2	0.7025
cAMP-dependent protein kinase catalytic subunit alpha	P00517	KAPCA_BOVIN	Bos taurus	2	0.7024
Mitogen-activated protein kinase 14	Q16539	MK14_HUMAN	Homo sapiens	3	0.7023
Aldehyde dehydrogenase, mitochondrial	P05091	ALDH2_HUMAN	Homo sapiens	3	0.7015
L-lactate dehydrogenase A chain	P13491	LDHA_RABIT	Oryctolagus cuniculus	2	0.7015
CCA-adding enzyme	O28126	CCA_ARCFU	Archaeoglobus fulgidus	2	0.7005
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	2	0.7005

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