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Rhusflavone

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

Canonical Smiles	Oc1ccc(cc1)[C@@H]1CC(=O)c2c(O1)cc(c(c2O)c1c(O)cc(c2c1O[C@@H](CC2=O)c1ccc(cc1)O)O)O
InChI	InChI=1S/C30H22O10/c31-15-5-1-13(2-6-15)22-11-20(36)26-24(39-22)12-21(37)27(29(26)38)28-18(34)9-17(33)25-19(35)10-23(40-30(25)28)14-3-7-16(32)8-4-14/h1-9,12,22-23,31-34,37-38H,10-11H2/t22-,23-/m0/s1
InChIKey	YBDIZQWDBBOOFB-GOTSBHOMSA-N
Formula	C₃₀H₂₂O₁₀
HBA	10
HBD	6
MW	542.5
Rotatable Bonds	3
TPSA	173.98
LogP	5.0
Number Rings	6
Number Aromatic Rings	4
Heavy Atom Count	40
Formal Charge	0
Fraction CSP3	0.13
Exact Mass	542.12
Number of Lipinski Rule Violations	3

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Rhabdophyllum arnoldianum	Ochnaceae	Plantae	1501067

Showing of synonyms

Mbing JN, Missi MB, et al. (2014). New flavonoids C-glycosides from Rhabdophyllum arnoldianum.. Natural product research,2014, 28(8), 539-544. [View] [PubMed]

Pubchem: 12114300

Cas: 53060-72-3

Gnps: CCMSLIB00004710194

Zinc: ZINC000026256601

Nmrshiftdb2: 60079166

No compound-protein relationship available.

SMILES: c1ccccc1C(CC2=O)Oc(c23)c(ccc3)-c(c4)ccc(c45)OC(CC5=O)c6ccccc6

Level: 3

Mol. Weight: 542.5 g/mol

SMILES: O=C1CCOc(c12)ccc(c2)-c(ccc3)c(c34)OC(CC4=O)c5ccccc5

Level: 2

Mol. Weight: 542.5 g/mol

SMILES: O=C1CCOc(c12)c(ccc2)-c(c3)ccc(c34)OC(CC4=O)c5ccccc5

Level: 2

Mol. Weight: 542.5 g/mol

SMILES: O=C1CCOc(c12)c(ccc2)-c(c3)ccc(c34)OCCC4=O

Level: 1

Mol. Weight: 542.5 g/mol

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

Level: 1

Mol. Weight: 542.5 g/mol

SMILES: c1cccc(c12)OCCC2=O

Level: 0

Mol. Weight: 542.5 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 542.5 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -6.32
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Non-Absorbed
Madin-Darby Canine Kidney: -5.040
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: 4.26

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 1.030
Plasma Protein Binding: 92.41
Steady State Volume of Distribution: -

Metabolism

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

Excretion

Clearance: 10.460
Organic Cation Transporter 2: Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: -0.010
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Toxic
Eye Corrosion: Safe
Eye Irritation: Toxic
Maximum Tolerated Dose: 0.980
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 6.330
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: -5497.640
Rat (Acute): 2.430
Rat (Chronic Oral): 3.520
Fathead Minnow: 18.410
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: 556.360
Hydration Free Energy: -3.100
Log(D) at pH=7.4: 3.250
Log(P): 4.5
Log S: -7.25
Log(Vapor Pressure): -8.9
Melting Point: 288.22
pKa Acid: 7.66
pKa Basic: 6.29

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	0.9555
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.9437
Histone deacetylase 4	P56524	HDAC4_HUMAN	Homo sapiens	3	0.9373
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha	Q04631	FNTA_RAT	Rattus norvegicus	3	0.8928
Polyribonucleotide nucleotidyltransferase	A7ZS61	PNP_ECO24	Escherichia coli O139:H28	4	0.8922
Homoserine dehydrogenase	P31116	DHOM_YEAST	Saccharomyces cerevisiae	4	0.8655
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	4	0.8614
Caspase-6	P55212	CASP6_HUMAN	Homo sapiens	3	0.8594
Serine/threonine-protein kinase pim-1	P11309	PIM1_HUMAN	Homo sapiens	3	0.8559
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.8545
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	4	0.8527
Pantothenate synthetase	P9WIL5	PANC_MYCTU	Mycobacterium tuberculosis	3	0.8522
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	4	0.8445
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform	O02697	PK3CG_PIG	Sus scrofa	5	0.8443
Bifunctional epoxide hydrolase 2	P34913	HYES_HUMAN	Homo sapiens	3	0.8347
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	3	0.8324
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	4	0.8281
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.8227
Carbonyl reductase [NADPH] 1	P16152	CBR1_HUMAN	Homo sapiens	3	0.8083
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha	Q4WP27	Q4WP27_ASPFU	Aspergillus fumigatus	3	0.8014
Endoplasmin	P41148	ENPL_CANLF	Canis lupus familiaris	4	0.7974
Acetylcholinesterase	P21836	ACES_MOUSE	Mus musculus	3	0.7845
Coagulation factor X	P00742	FA10_HUMAN	Homo sapiens	3	0.7809
Glucose-1-phosphate thymidylyltransferase	Q9HU22	Q9HU22_PSEAE	Pseudomonas aeruginosa	3	0.7757
HTH-type transcriptional regulator TtgR	Q9AIU0	TTGR_PSEPT	Pseudomonas putida	3	0.7757
Riboflavin synthase	P0AFU8	RISA_ECOLI	Escherichia coli	4	0.7703
Dipeptidyl peptidase 4	P27487	DPP4_HUMAN	Homo sapiens	3	0.7700
Kinesin-like protein KIF11	P52732	KIF11_HUMAN	Homo sapiens	3	0.7597
HTH-type transcriptional regulator QacR	P0A0N3	QACR_STAAM	Staphylococcus aureus	3	0.7585
3-hydroxy-3-methylglutaryl-coenzyme A reductase	P04035	HMDH_HUMAN	Homo sapiens	3	0.7485
Collagenase 3	P45452	MMP13_HUMAN	Homo sapiens	4	0.7471
Gag-Pol polyprotein	P04584	POL_HV2RO	Human immunodeficiency virus type 2 subtype A	4	0.7463
Disintegrin and metalloproteinase domain-containing protein 17	P78536	ADA17_HUMAN	Homo sapiens	3	0.7451
Polymerase basic protein 2	Q2LG68	Q2LG68_9INFA	Influenza A virus)	5	0.7401
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7377
D-aminoacyl-tRNA deacylase	Q8IIS0	DTD_PLAF7	Plasmodium falciparum	3	0.7370
Caffeoyl-CoA O-methyltransferase	Q40313	CAMT_MEDSA	Medicago sativa	3	0.7363
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7349
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7340
Hygromycin-B 4-O-kinase	P00557	KHYB_ECOLX	Escherichia coli	3	0.7335
2-C-methyl-D-erythritol 2,4-cyclodiphosphate synthase	Q3JRA0	ISPF_BURP1	Burkholderia pseudomallei	4	0.7318
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	4	0.7302
Ras-related protein Ral-B	P11234	RALB_HUMAN	Homo sapiens	3	0.7299
cGMP-dependent 3',5'-cyclic phosphodiesterase	O00408	PDE2A_HUMAN	Homo sapiens	3	0.7239
Cyclin-dependent kinase 9	P50750	CDK9_HUMAN	Homo sapiens	3	0.7221
2-aminohexano-6-lactam racemase	Q7M181	ACLR_ACHOB	Achromobacter obae	2	0.7219
Anthocyanidin 3-O-glucosyltransferase UFGT	P51094	UFOG_VITVI	Vitis vinifera	4	0.7206
Threonine--tRNA ligase	P0A8M3	SYT_ECOLI	Escherichia coli	3	0.7159
GTPase KRas	P01116	RASK_HUMAN	Homo sapiens	3	0.7151
Probable enoyl-CoA hydratase EchA8	P9WNN9	ECHA8_MYCTU	Mycobacterium tuberculosis	3	0.7149
3-hydroxy-3-methylglutaryl-coenzyme A reductase	P04035	HMDH_HUMAN	Homo sapiens	3	0.7140
Tyrosine-protein kinase ABL1	P00519	ABL1_HUMAN	Homo sapiens	3	0.7137
Thymidylate synthase	P00469	TYSY_LACCA	Lacticaseibacillus casei	3	0.7121
Peptidyl-prolyl cis-trans isomerase FKBP1A	P62942	FKB1A_HUMAN	Homo sapiens	3	0.7114
YbaK/aminoacyl-tRNA synthetase-associated domain-containing protein	Q5SHN1	Q5SHN1_THET8	Thermus thermophilus	3	0.7112
Aurora kinase A	O14965	AURKA_HUMAN	Homo sapiens	3	0.7106
Serpin domain-containing protein	H0ZQY2	H0ZQY2_TAEGU	Taeniopygia guttata	3	0.7102
GTPase HRas	P01112	RASH_HUMAN	Homo sapiens	3	0.7097
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform	P48736	PK3CG_HUMAN	Homo sapiens	3	0.7084
4-hydroxyphenylacetate 3-monooxygenase	Q8YHT7	Q8YHT7_BRUME	Brucella melitensis biotype 1	2	0.7074
Valacyclovir hydrolase	Q86WA6	BPHL_HUMAN	Homo sapiens	3	0.7074
Basic phospholipase A2 homolog piratoxin-1	P58399	PA2H1_BOTPI	Bothrops pirajai	4	0.7064
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7052
Pentaerythritol tetranitrate reductase	P71278	P71278_ENTCL	Enterobacter cloacae	2	0.7047
Calmodulin	P62157	CALM_BOVIN	Bos taurus	3	0.7025
Catechol O-methyltransferase	P22734	COMT_RAT	Rattus norvegicus	3	0.7025

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