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Fraxidin

Family: Plantae - Rubiaceae
Kingdom: Plantae
Class: Coumarin
- Subclass: Hydroxycoumarin

Canonical Smiles	COc1c(OC)cc2c(c1O)oc(=O)cc2
InChI	InChI=1S/C11H10O5/c1-14-7-5-6-3-4-8(12)16-10(6)9(13)11(7)15-2/h3-5,13H,1-2H3
InChIKey	QNFBKOHHLAWWTC-UHFFFAOYSA-N
Formula	C₁₁H₁₀O₅
HBA	5
HBD	1
MW	222.2
Rotatable Bonds	2
TPSA	68.9
LogP	1.52
Number Rings	2
Number Aromatic Rings	2
Heavy Atom Count	16
Formal Charge	0
Fraction CSP3	0.18
Exact Mass	222.05
Number of Lipinski Rule Violations	0

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Erythrina mildbraedii	Leguminosae/Fabaceae	Plantae	2708827
2	Morinda lucida	Rubiaceae	Plantae	339305

Showing of synonyms

Tchokouaha RF, Alexi X, et al. (2010). Erymildbraedin A and B, two novel cytotoxic dimethylpyrano-isoflavones from the stem bark of Erythrina mildbraedii: evaluation of their activity toward endocrine cancer cells.. Journal of enzyme inhibition and medicinal chemistry,2010, 25(2), 228-233. [View] [PubMed]
Mfonku NA, Tadjong AT, et al. (2021). Isolation and characterization of antisalmonellal anthraquinones and coumarins from Morinda lucida Benth. (Rubiaceae). Chem. Pap. 2021, 75, 2067-2073. [View]

Pubchem: 3083616

Cas: 525-21-3

Gnps: CCMSLIB00006417179

Zinc: ZINC000002566165

Kegg Ligand: C17479

Chebi: 81120

Nmrshiftdb2: 76066

Chembl: CHEMBL2334351

Comptox: DTXSID70200499

Bindingdb: 50428430

CPRiL: 218454

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

Level: 0

Mol. Weight: 222.2 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -4.51
Human Oral Bioavailability 20%: Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.190
Human Oral Bioavailability 50%: Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -2.1

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Penetrable
Fraction Unbound (Human): 0.990
Plasma Protein Binding: 52.22
Steady State Volume of Distribution: -

Metabolism

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

Excretion

Clearance: 6.840
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: 1.420
Biodegradation: Toxic
Carcinogenesis: Safe
Crustacean: Safe
Liver Injury I (DILI): Toxic
Eye Corrosion: Safe
Eye Irritation: Toxic
Maximum Tolerated Dose: 1.470
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 5.480
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: 3.510
Rat (Acute): 2.100
Rat (Chronic Oral): 2.100
Fathead Minnow: 4.150
Respiratory Disease: Safe
Skin Sensitisation: Safe
SR-ARE: Safe
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Safe
SR-p53: Safe

General Properties

Boiling Point: 355.960
Hydration Free Energy: -9.230
Log(D) at pH=7.4: 0.820
Log(P): 1.08
Log S: -2.44
Log(Vapor Pressure): -4.74
Melting Point: 153.16
pKa Acid: 6.35
pKa Basic: 2.29

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Biflaviolin synthase CYP158A1	Q9KZF5	C1581_STRCO	Streptomyces coelicolor / M145)	3	0.9649
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.9329
Toxoflavin degrading enzyme	E3SET7	E3SET7_PAEPO	Paenibacillus polymyxa	3	0.9233
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.9230
NAD(P)H-hydrate epimerase	Q8K4Z3	NNRE_MOUSE	Mus musculus	3	0.9205
Bromodomain-containing protein 2	P25440	BRD2_HUMAN	Homo sapiens	3	0.9177
Biflaviolin synthase CYP158A2	Q9FCA6	C1582_STRCO	Streptomyces coelicolor / M145)	3	0.9145
MAP kinase-activated protein kinase 2	P49137	MAPK2_HUMAN	Homo sapiens	3	0.9138
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.9138
Photosynthetic reaction center cytochrome c subunit	P07173	CYCR_BLAVI	Blastochloris viridis	3	0.9082
NAD-capped RNA hydrolase NudC	P32664	NUDC_ECOLI	Escherichia coli	3	0.8943
Biflaviolin synthase CYP158A2	Q9FCA6	C1582_STRCO	Streptomyces coelicolor / M145)	3	0.8893
Photosynthetic reaction center cytochrome c subunit	P07173	CYCR_BLAVI	Blastochloris viridis	3	0.8890
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.8885
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.8878
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.8877
2-phospho-L-lactate transferase	Q8PVT6	COFD_METMA	Methanosarcina mazei	3	0.8865
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.8787
Glutamate receptor 2	P19491	GRIA2_RAT	Rattus norvegicus	3	0.8714
Gag-Pol polyprotein	P03369	POL_HV1A2	Human immunodeficiency virus type 1 group M subtype B	3	0.8634
Phenylalanine-4-hydroxylase	P00439	PH4H_HUMAN	Homo sapiens	3	0.8599
Uridine phosphorylase	Q5XA29	Q5XA29_STRP6	Streptococcus pyogenes serotype M6	4	0.8483
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase	Q9TQS6	DHDH_MACFA	Macaca fascicularis	3	0.8465
Bromodomain-containing protein 2	P25440	BRD2_HUMAN	Homo sapiens	3	0.8431
Glutamate receptor 2	P19491	GRIA2_RAT	Rattus norvegicus	3	0.8405
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	3	0.8384
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	2	0.8310
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.8307
Lysozyme C II	P11941	LYSC2_ONCMY	Oncorhynchus mykiss	3	0.8164
APH(2'')-Id	O68183	O68183_ENTCA	Enterococcus casseliflavus	4	0.8059
Thymidylate synthase	P0A884	TYSY_ECOLI	Escherichia coli	2	0.8027
Glutamate receptor 2	P19491	GRIA2_RAT	Rattus norvegicus	3	0.8002
Aminoglycoside N(3)-acetyltransferase	A0A3P1UCA6	Q81P86_BACAN	Bacillus anthracis	3	0.7958
Soluble cytochrome b562	P0ABE7	C562_ECOLX	Escherichia coli	3	0.7888
Dual specificity mitogen-activated protein kinase kinase 1	Q02750	MP2K1_HUMAN	Homo sapiens	3	0.7875
Acetylcholinesterase	P04058	ACES_TETCF	Tetronarce californica	3	0.7870
Acetylcholinesterase	P04058	ACES_TETCF	Tetronarce californica	3	0.7847
NAD(P)H-hydrate epimerase	Q8K4Z3	NNRE_MOUSE	Mus musculus	3	0.7843
NADH:flavin oxidoreductase Sye1	Q8EEC8	Q8EEC8_SHEON	Shewanella oneidensis	3	0.7813
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7755
Ribosomal small subunit pseudouridine synthase A	P0AA43	RSUA_ECOLI	Escherichia coli	3	0.7621
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform	P48736	PK3CG_HUMAN	Homo sapiens	3	0.7580
Deoxycytidine kinase	P27707	DCK_HUMAN	Homo sapiens	4	0.7527
Putative S-adenosyl-L-methionine-dependent methyltransferase ML2640	Q9CCZ4	Y2640_MYCLE	Mycobacterium leprae	3	0.7510
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7453
Serine/threonine-protein kinase 24	Q9Y6E0	STK24_HUMAN	Homo sapiens	3	0.7423
4-hydroxy-7-methoxy-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-2-yl glucoside beta-D-glucosidase 1b, chloroplastic	Q1XH05	HGL1B_WHEAT	Triticum aestivum	3	0.7388
Tyrosine-protein kinase JAK3	P52333	JAK3_HUMAN	Homo sapiens	3	0.7384
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	2	0.7370
O-GlcNAcase NagJ	Q0TR53	OGA_CLOP1	Clostridium perfringens	3	0.7360
Ribonuclease J	H9CZL7	H9CZL7_DEIRD	Deinococcus radiodurans	3	0.7359
ADP-ribosylation factor 1	P84077	ARF1_HUMAN	Homo sapiens	2	0.7349
Mitochondrial poly(A) polymerase	F1NBW0	F1NBW0_CHICK	Gallus gallus	2	0.7287
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7284
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	3	0.7281
Agglutinin alpha chain	P18674	LECA_MACPO	Maclura pomifera	3	0.7275
cAMP-dependent protein kinase catalytic subunit alpha	P00517	KAPCA_BOVIN	Bos taurus	3	0.7270
Cytidine and deoxycytidylate deaminase zinc-binding region	Q82Y41	Q82Y41_NITEU	Nitrosomonas europaea	3	0.7251
Histone-lysine N-methyltransferase SETD7	Q8WTS6	SETD7_HUMAN	Homo sapiens	3	0.7236
Uncharacterized protein	Q3F0V8	Q3F0V8_BACTI	Bacillus thuringiensis serovar israelensis ATCC 35646	3	0.7231
Flavin-dependent thymidylate synthase	Q9WYT0	THYX_THEMA	Thermotoga maritima	3	0.7208
Methionine aminopeptidase	P0AE18	MAP1_ECOLI	Escherichia coli	3	0.7206
Ribosome-inactivating protein 3	P25891	RIP3_MAIZE	Zea mays	3	0.7201
Kynurenine/alpha-aminoadipate aminotransferase, mitochondrial	Q8N5Z0	AADAT_HUMAN	Homo sapiens	2	0.7200
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7196
Dual specificity mitogen-activated protein kinase kinase 1	Q02750	MP2K1_HUMAN	Homo sapiens	3	0.7181
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.7175
Thymidylate kinase	Q9KQI2	KTHY_VIBCH	Vibrio cholerae serotype O1	4	0.7147
Proton-gated ion channel	Q7NDN8	GLIC_GLOVI	Gloeobacter violaceus	3	0.7141
L-lactate dehydrogenase	Q5SJA1	LDH_THET8	Thermus thermophilus	3	0.7128
LIM domain kinase 1	P53667	LIMK1_HUMAN	Homo sapiens	2	0.7127
Fibroblast growth factor receptor 2	P21802	FGFR2_HUMAN	Homo sapiens	3	0.7124
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta	P78356	PI42B_HUMAN	Homo sapiens	3	0.7124
CREB-binding protein	Q92793	CBP_HUMAN	Homo sapiens	3	0.7122
Adenosine kinase	Q9TVW2	ADK_TOXGO	Toxoplasma gondii	3	0.7121
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7121
Acetylcholinesterase	P04058	ACES_TETCF	Tetronarce californica	3	0.7100
1-deoxy-D-xylulose 5-phosphate reductoisomerase	P45568	DXR_ECOLI	Escherichia coli	2	0.7100
Ribosomal small subunit pseudouridine synthase A	P0AA43	RSUA_ECOLI	Escherichia coli	3	0.7098
Adenylate cyclase type 5	P30803	ADCY5_CANLF	Canis lupus familiaris	3	0.7098
rRNA N-glycosylase	D9J2T9	D9J2T9_MOMBA	Momordica balsamina	3	0.7077
Acetylcholinesterase	P22303	ACES_HUMAN	Homo sapiens	3	0.7065
Carbonic anhydrase 1	P00915	CAH1_HUMAN	Homo sapiens	2	0.7061
Achbp	I6L8L2	I6L8L2_CAPTE	Capitella teleta	3	0.7050
Cytosolic IMP-GMP specific 5'-nucleotidase	Q5ZZB6	Q5ZZB6_LEGPH	Legionella pneumophila subsp. pneumophila	3	0.7040
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	3	0.7015
GTPase IMAP family member 2	Q9UG22	GIMA2_HUMAN	Homo sapiens	3	0.7002
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.7001

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