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Calodenin B

Family: Plantae - Ochnaceae
Kingdom: Plantae
Class: Flavonoid
- Subclass: Isomeric Biflavonoid

Canonical Smiles	Oc1ccc(cc1)c1oc2c(c1C(=O)c1ccc(cc1O)O)c(O)cc(c2C(=O)/C=C/c1ccc(cc1)O)O
InChI	InChI=1S/C30H20O9/c31-17-6-1-15(2-7-17)3-12-21(34)25-23(36)14-24(37)26-27(28(38)20-11-10-19(33)13-22(20)35)29(39-30(25)26)16-4-8-18(32)9-5-16/h1-14,31-33,35-37H/b12-3+
InChIKey	OYSSHUWICGHBOU-KGVSQERTSA-N
Formula	C₃₀H₂₀O₉
HBA	9
HBD	6
MW	524.48
Rotatable Bonds	6
TPSA	168.66
LogP	5.46
Number Rings	5
Number Aromatic Rings	5
Heavy Atom Count	39
Formal Charge	0
Fraction CSP3	0.0
Exact Mass	524.11
Number of Lipinski Rule Violations	3

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Ochna holstii	Ochnaceae	Plantae	1389766
2	Ochna kirkii	Ochnaceae	Plantae	2699567

Showing of synonyms

Kalenga TM, Ndoile MM, et al. (2021). Antibacterial and cytotoxic biflavonoids from the root bark of Ochna kirkii. Fitoterapia,2021, 151(), 104857. [View] [PubMed]
Kalenga TM, Ndoile MM, et al. (2021). Biflavanones, Chalconoids, and Flavonoid Analogues from the Stem Bark of Ochna holstii. Journal of natural products,2021, 84(2), 364-372. [View] [PubMed]

Pubchem: 10007020

Zinc: ZINC000095909990

Nmrshiftdb2: 70051587

Chembl: CHEMBL5182711

No compound-protein relationship available.

SMILES: c1ccccc1C=CC(=O)c(ccc2)c(c23)oc(-c4ccccc4)c3C(=O)c5ccccc5

Level: 3

Mol. Weight: 524.48 g/mol

SMILES: c1ccccc1C=CC(=O)c(ccc2)c(c23)occ3C(=O)c4ccccc4

Level: 2

Mol. Weight: 524.48 g/mol

SMILES: c1ccccc1C=CC(=O)c(ccc2)c(c23)oc(c3)-c4ccccc4

Level: 2

Mol. Weight: 524.48 g/mol

SMILES: c1ccccc1C(=O)c2c(-c3ccccc3)oc(c24)cccc4

Level: 2

Mol. Weight: 524.48 g/mol

SMILES: c1coc(c12)c(ccc2)C(=O)C=Cc3ccccc3

Level: 1

Mol. Weight: 524.48 g/mol

SMILES: c1ccccc1C(=O)c2coc(c23)cccc3

Level: 1

Mol. Weight: 524.48 g/mol

SMILES: c1cccc(c12)oc(c2)-c3ccccc3

Level: 1

Mol. Weight: 524.48 g/mol

SMILES: c1coc(c12)cccc2

Level: 0

Mol. Weight: 524.48 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 524.48 g/mol

Antibacterial

Absorption

Caco-2 (logPapp): -6.06
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -5.080
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: 2.26

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 1.220
Plasma Protein Binding: 92.12
Steady State Volume of Distribution: -

Metabolism

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

Excretion

Clearance: 6.800
Organic Cation Transporter 2: Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: 0.860
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Toxic
Eye Corrosion: Safe
Eye Irritation: Toxic
Maximum Tolerated Dose: 1.150
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 6.120
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: -3279.040
Rat (Acute): 2.320
Rat (Chronic Oral): 4.130
Fathead Minnow: 17.690
Respiratory Disease: Safe
Skin Sensitisation: Safe
SR-ARE: Toxic
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Toxic
SR-p53: Toxic

General Properties

Boiling Point: 606.880
Hydration Free Energy: -3.060
Log(D) at pH=7.4: 3.390
Log(P): 6.31
Log S: -7.29
Log(Vapor Pressure): -9.1
Melting Point: 313.03
pKa Acid: 8.65
pKa Basic: 6.95

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.9278
Macrophage metalloelastase	P39900	MMP12_HUMAN	Homo sapiens	3	0.9211
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	3	0.9197
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.9195
Dihydrofolate reductase	P00378	DYR_CHICK	Gallus gallus	3	0.9102
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.9053
Pantothenate synthetase	P9WIL5	PANC_MYCTU	Mycobacterium tuberculosis	3	0.8989
Urokinase-type plasminogen activator	P00749	UROK_HUMAN	Homo sapiens	3	0.8967
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.8922
Riboflavin synthase	P0AFU8	RISA_ECOLI	Escherichia coli	4	0.8778
Histone deacetylase 4	P56524	HDAC4_HUMAN	Homo sapiens	3	0.8733
Phospholipase A2, major isoenzyme	P00592	PA21B_PIG	Sus scrofa	3	0.8700
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.8592
Purine nucleoside phosphorylase DeoD-type	P0ABP9	DEOD_ECO57	Escherichia coli O157:H7	3	0.8536
Thymidylate synthase	P00469	TYSY_LACCA	Lacticaseibacillus casei	3	0.8490
Acetylcholinesterase	P21836	ACES_MOUSE	Mus musculus	3	0.8438
Matrilysin	P09237	MMP7_HUMAN	Homo sapiens	4	0.8421
Ectonucleoside triphosphate diphosphohydrolase I	Q5ZUA2	Q5ZUA2_LEGPH	Legionella pneumophila subsp. pneumophila	3	0.8374
Purine nucleoside phosphorylase DeoD-type	P0ABP9	DEOD_ECO57	Escherichia coli O157:H7	3	0.8325
Purine nucleoside phosphorylase DeoD-type	P0ABP8	DEOD_ECOLI	Escherichia coli	3	0.8320
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	3	0.8314
Geranylgeranyl transferase type-2 subunit alpha	Q08602	PGTA_RAT	Rattus norvegicus	3	0.8280
HTH-type transcriptional regulator QacR	P0A0N3	QACR_STAAM	Staphylococcus aureus	3	0.8271
HTH-type transcriptional regulator TtgR	Q9AIU0	TTGR_PSEPT	Pseudomonas putida	3	0.8217
Thymidylate synthase	P04818	TYSY_HUMAN	Homo sapiens	3	0.8217
Thymidylate synthase	P00469	TYSY_LACCA	Lacticaseibacillus casei	4	0.8193
Purine nucleoside phosphorylase DeoD-type	O34925	DEOD_BACSU	Bacillus subtilis	3	0.8150
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9QYJ6	PDE10_RAT	Rattus norvegicus	3	0.8082
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.8074
Caspase-6	P55212	CASP6_HUMAN	Homo sapiens	3	0.8065
Rhodopsin kinase GRK1	P28327	GRK1_BOVIN	Bos taurus	3	0.8063
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.8028
Ribonuclease 4	P15468	RNAS4_PIG	Sus scrofa	3	0.7982
Serine/threonine-protein kinase 10	O94804	STK10_HUMAN	Homo sapiens	3	0.7918
Peroxisome proliferator-activated receptor gamma	P37231	PPARG_HUMAN	Homo sapiens	3	0.7903
Valacyclovir hydrolase	Q86WA6	BPHL_HUMAN	Homo sapiens	3	0.7889
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.7881
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	3	0.7874
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7866
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	3	0.7848
Serine/threonine-protein kinase 24	Q9Y6E0	STK24_HUMAN	Homo sapiens	3	0.7793
Methionine aminopeptidase 2	P50579	MAP2_HUMAN	Homo sapiens	3	0.7765
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7764
Tubulin alpha-1B chain	P81947	TBA1B_BOVIN	Bos taurus	3	0.7752
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.7749
cGMP-specific 3',5'-cyclic phosphodiesterase	O76074	PDE5A_HUMAN	Homo sapiens	3	0.7740
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7729
Threonine--tRNA ligase	P0A8M3	SYT_ECOLI	Escherichia coli	3	0.7672
Homoserine dehydrogenase	P31116	DHOM_YEAST	Saccharomyces cerevisiae	4	0.7662
UDP-N-acetylmuramoylalanine--D-glutamate ligase	P14900	MURD_ECOLI	Escherichia coli	3	0.7658
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	3	0.7635
UDP-N-acetylglucosamine 1-carboxyvinyltransferase	P33038	MURA_ENTCC	Enterobacter cloacae subsp. cloacae	3	0.7626
Protein S100-A13	Q99584	S10AD_HUMAN	Homo sapiens	3	0.7623
Peroxisome proliferator-activated receptor gamma	P37231	PPARG_HUMAN	Homo sapiens	4	0.7591
Mycocyclosin synthase	P9WPP7	CP121_MYCTU	Mycobacterium tuberculosis	3	0.7584
Formate--tetrahydrofolate ligase	P21164	FTHS_MOOTH	Moorella thermoacetica	3	0.7584
Purine nucleoside phosphorylase DeoD-type	Q5EEL8	DEOD_BACCE	Bacillus cereus	3	0.7579
L-lactate dehydrogenase A chain	P00338	LDHA_HUMAN	Homo sapiens	4	0.7577
Kinesin-like protein KIF11	P52732	KIF11_HUMAN	Homo sapiens	3	0.7556
Urokinase-type plasminogen activator	P00749	UROK_HUMAN	Homo sapiens	3	0.7533
Collagenase 3	P45452	MMP13_HUMAN	Homo sapiens	4	0.7522
UDP-N-acetylmuramoyl-tripeptide--D-alanyl-D-alanine ligase	Q8DNV6	Q8DNV6_STRR6	Streptococcus pneumoniae	3	0.7513
Secoisolariciresinol dehydrogenase	Q94KL8	SILD_PODPE	Podophyllum peltatum	4	0.7501
Hypoxanthine phosphoribosyltransferase	Q4DRC4	Q4DRC4_TRYCC	Trypanosoma cruzi	3	0.7454
3-hydroxy-3-methylglutaryl-coenzyme A reductase	P04035	HMDH_HUMAN	Homo sapiens	3	0.7410
Hygromycin-B 4-O-kinase	P00557	KHYB_ECOLX	Escherichia coli	3	0.7406
Orotidine 5'-phosphate decarboxylase	Q5L0U0	PYRF_GEOKA	Geobacillus kaustophilus	3	0.7402
Bis(5'-adenosyl)-triphosphatase	P49789	FHIT_HUMAN	Homo sapiens	3	0.7386
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7377
Methionine aminopeptidase	P0AE18	MAP1_ECOLI	Escherichia coli	3	0.7364
Proto-oncogene tyrosine-protein kinase Src	P00523	SRC_CHICK	Gallus gallus	3	0.7363
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	3	0.7350
17beta-hydroxysteroid dehydrogenase	O93874	O93874_COCLU	Cochliobolus lunatus	3	0.7328
Ribonuclease TTHA0252	Q5SLP1	RNSE_THET8	Thermus thermophilus	3	0.7320
Phosphoenolpyruvate carboxykinase [GTP]	A5TYT6	PCKG_MYCTA	Mycobacterium tuberculosis	3	0.7313
Apoptosis regulator Bcl-2	P10415	BCL2_HUMAN	Homo sapiens	3	0.7310
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	3	0.7309
MAP kinase-activated protein kinase 2	P49137	MAPK2_HUMAN	Homo sapiens	4	0.7300
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	2	0.7300
Carnitine O-acetyltransferase	P47934	CACP_MOUSE	Mus musculus	3	0.7296
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.7294
Histone-lysine N-methyltransferase SETD7	Q8WTS6	SETD7_HUMAN	Homo sapiens	3	0.7281
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	3	0.7277
Adenosine monophosphate-protein transferase	Q8ZVF7	Q8ZVF7_PYRAE	Pyrobaculum aerophilum	3	0.7276
D-aminoacyl-tRNA deacylase	Q8IIS0	DTD_PLAF7	Plasmodium falciparum	3	0.7270
Dihydrofolate reductase	P0ABQ4	DYR_ECOLI	Escherichia coli	4	0.7245
Tyrosine-protein kinase JAK3	P52333	JAK3_HUMAN	Homo sapiens	3	0.7244
Phosphodiesterase	Q8WQX9	Q8WQX9_9TRYP	Trypanosoma brucei	3	0.7232
2-aminohexano-6-lactam racemase	Q7M181	ACLR_ACHOB	Achromobacter obae	2	0.7210
Nonspecific lipid-transfer protein, putative	C9ZUV7	C9ZUV7_TRYB9	Trypanosoma brucei gambiense	3	0.7207
Thymidylate synthase	P00469	TYSY_LACCA	Lacticaseibacillus casei	3	0.7185
Beta-ketoacyl-[acyl-carrier-protein] synthase III	P0A6R0	FABH_ECOLI	Escherichia coli	3	0.7174
Peroxisome proliferator-activated receptor gamma	P37231	PPARG_HUMAN	Homo sapiens	3	0.7160
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	3	0.7149
Glutamate receptor ionotropic, kainate 1	P22756	GRIK1_RAT	Rattus norvegicus	3	0.7146
cAMP-dependent protein kinase catalytic subunit alpha	P17612	KAPCA_HUMAN	Homo sapiens	5	0.7141
Nitrogenase iron protein 1	P00459	NIFH1_AZOVI	Azotobacter vinelandii	3	0.7122
Biotin carboxylase	P24182	ACCC_ECOLI	Escherichia coli	5	0.7118
Phosphoenolpyruvate carboxykinase [GTP]	P9WIH3	PCKG_MYCTU	Mycobacterium tuberculosis	3	0.7107
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.7092
Purine nucleoside phosphorylase DeoD-type	O34925	DEOD_BACSU	Bacillus subtilis	3	0.7072
Laccase	P07788	COTA_BACSU	Bacillus subtilis	3	0.7065
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7061
5-formyltetrahydrofolate cyclo-ligase	P75430	MTHFS_MYCPN	Mycoplasma pneumoniae	2	0.7060
S-adenosylmethionine decarboxylase proenzyme	P17707	DCAM_HUMAN	Homo sapiens	3	0.7058
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	2	0.7054
Flavin-dependent thymidylate synthase	Q9WYT0	THYX_THEMA	Thermotoga maritima	3	0.7040
Prostaglandin reductase 1	Q14914	PTGR1_HUMAN	Homo sapiens	5	0.7038
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7013
Metallo-beta-lactamase type 2	C7C422	BLAN1_KLEPN	Klebsiella pneumoniae	3	0.7010
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.7009
Thymidylate synthase	P00469	TYSY_LACCA	Lacticaseibacillus casei	3	0.7008
Transthyretin	P02767	TTHY_RAT	Rattus norvegicus	3	0.7006

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