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(2R,3S,2''S)-3''',4',4''',5,5'',7,7''-heptahydroxy-3,8"-biflavanone

Family: Plantae - Onagraceae
Kingdom: Plantae
Class: Flavonoid

Canonical Smiles	Oc1ccc(cc1)[C@@H]1Oc2cc(O)cc(c2C(=O)[C@H]1c1c(O)cc(c2c1O[C@@H](CC2=O)c1ccc(c(c1)O)O)O)O
InChI	InChI=1S/C30H22O11/c31-14-4-1-12(2-5-14)29-27(28(39)25-18(35)8-15(32)9-23(25)41-29)26-20(37)10-19(36)24-21(38)11-22(40-30(24)26)13-3-6-16(33)17(34)7-13/h1-10,22,27,29,31-37H,11H2/t22-,27+,29-/m0/s1
InChIKey	IMIXFUXOSFSXPC-JWMKGCOUSA-N
Formula	C₃₀H₂₂O₁₁
HBA	11
HBD	7
MW	558.5
Rotatable Bonds	3
TPSA	194.21
LogP	4.43
Number Rings	6
Number Aromatic Rings	4
Heavy Atom Count	41
Formal Charge	0
Fraction CSP3	0.13
Exact Mass	558.12
Number of Lipinski Rule Violations	3

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Ludwigia leptocarpa	Onagraceae	Plantae	1401410

Showing of synonyms

Mabou FD, Tamokou JD, et al. (2016). Complex secondary metabolites from Ludwigia leptocarpa with potent antibacterial and antioxidant activities.. Drug discoveries & therapeutics,2016, 10(3), 141-149. [View] [PubMed]

Pubchem: 102223069

Zinc: ZINC000026189531

Nmrshiftdb2: 70098826

No compound-protein relationship available.

SMILES: c1ccccc1C(CC2=O)Oc(c23)c(ccc3)C(C4=O)C(c5ccccc5)Oc(c46)cccc6

Level: 3

Mol. Weight: 558.5 g/mol

SMILES: c1ccccc1C(CC2=O)Oc(c23)c(ccc3)C(C4=O)COc(c45)cccc5

Level: 2

Mol. Weight: 558.5 g/mol

SMILES: O=C1CCOc(c12)c(ccc2)C(C3=O)C(c4ccccc4)Oc(c35)cccc5

Level: 2

Mol. Weight: 558.5 g/mol

SMILES: O=C1CCOc(c12)c(ccc2)C(C3=O)COc(c34)cccc4

Level: 1

Mol. Weight: 558.5 g/mol

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

Level: 1

Mol. Weight: 558.5 g/mol

SMILES: c1cccc(c12)OCCC2=O

Level: 0

Mol. Weight: 558.5 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 558.5 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -6.34
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Non-Absorbed
Madin-Darby Canine Kidney: -5.130
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: 4.82

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 1.090
Plasma Protein Binding: 94.4
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: Inhibitor
CYP 3A4 Substrate: Non-Substrate
OATP1B1: Inhibitor
OATP1B3: Non-Inhibitor

Excretion

Clearance: 11.320
Organic Cation Transporter 2: Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: -0.940
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Toxic
Eye Corrosion: Safe
Eye Irritation: Toxic
Maximum Tolerated Dose: 1.070
Liver Injury II: Toxic
hERG Blockers: Toxic
Daphnia Maga: 6.770
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: Toxic
T. Pyriformis: -7920.990
Rat (Acute): 2.400
Rat (Chronic Oral): 3.880
Fathead Minnow: 22.260
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: 542.980
Hydration Free Energy: -3.130
Log(D) at pH=7.4: 2.590
Log(P): 4.37
Log S: -6.3
Log(Vapor Pressure): -10.01
Melting Point: 315.53
pKa Acid: 8.96
pKa Basic: 6.25

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Acetolactate synthase, chloroplastic	P17597	ILVB_ARATH	Arabidopsis thaliana	3	0.8919
Prostaglandin reductase 3	Q8N4Q0	PTGR3_HUMAN	Homo sapiens	5	0.8861
Ras-related protein Ral-B	P11234	RALB_HUMAN	Homo sapiens	3	0.8701
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	4	0.8640
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.8574
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.8524
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	4	0.8504
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.8377
Collagenase 3	P45452	MMP13_HUMAN	Homo sapiens	4	0.8367
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8239
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	3	0.8197
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8189
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha	Q04631	FNTA_RAT	Rattus norvegicus	3	0.8165
Acetolactate synthase, chloroplastic	P17597	ILVB_ARATH	Arabidopsis thaliana	3	0.8146
Phospholipase A2, major isoenzyme	P00592	PA21B_PIG	Sus scrofa	3	0.8081
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	3	0.8019
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.8009
Annexin A5	P08758	ANXA5_HUMAN	Homo sapiens	3	0.7999
Nitric oxide synthase oxygenase	O34453	NOSO_BACSU	Bacillus subtilis	4	0.7937
Leucoanthocyanidin dioxygenase	Q96323	LDOX_ARATH	Arabidopsis thaliana	4	0.7883
Leucoanthocyanidin dioxygenase	Q96323	LDOX_ARATH	Arabidopsis thaliana	4	0.7819
Maltose/maltodextrin-binding periplasmic protein	P0AEX9	MALE_ECOLI	Escherichia coli	3	0.7788
Lactoperoxidase	P80025	PERL_BOVIN	Bos taurus	3	0.7778
Insulin-degrading enzyme	P14735	IDE_HUMAN	Homo sapiens	3	0.7720
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha	Q4WP27	Q4WP27_ASPFU	Aspergillus fumigatus	3	0.7717
[Pyruvate dehydrogenase (acetyl-transferring)] kinase isozyme 2, mitochondrial	Q15119	PDK2_HUMAN	Homo sapiens	3	0.7712
Polyprotein	Q80J95	Q80J95_9CALI	Murine norovirus 1	3	0.7696
Collagenase 3	P45452	MMP13_HUMAN	Homo sapiens	4	0.7690
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7667
Stromelysin-1	P08254	MMP3_HUMAN	Homo sapiens	4	0.7568
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7567
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.7567
Thymidylate synthase	P00469	TYSY_LACCA	Lacticaseibacillus casei	4	0.7554
Putative HMP/thiamine-binding protein YkoF	O34911	YKOF_BACSU	Bacillus subtilis	3	0.7498
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.7491
Transcriptional regulator, PadR-like family	A2RI36	A2RI36_LACLM	Lactococcus lactis subsp. cremoris	3	0.7489
Polyribonucleotide nucleotidyltransferase	A7ZS61	PNP_ECO24	Escherichia coli O139:H28	3	0.7446
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7381
Protease	O38896	O38896_9HIV1	Human immunodeficiency virus 1	3	0.7364
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7338
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	4	0.7337
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7268
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7178
D-aminoacyl-tRNA deacylase	Q8IIS0	DTD_PLAF7	Plasmodium falciparum	3	0.7157
Cyclic GMP-AMP phosphodiesterase SMPDL3A	Q92484	ASM3A_HUMAN	Homo sapiens	2	0.7152
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7113
Lethal(3)malignant brain tumor-like protein 1	Q9Y468	LMBL1_HUMAN	Homo sapiens	3	0.7102
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	3	0.7083
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7077
Gag-Pol polyprotein	P03367	POL_HV1BR	Human immunodeficiency virus type 1 group M subtype B	3	0.7067
Seminal ribonuclease	P00669	RNS_BOVIN	Bos taurus	3	0.7055
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.7040
HTH-type transcriptional regulator QacR	P0A0N4	QACR_STAAU	Staphylococcus aureus	5	0.7031
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7026
Casein kinase II subunit alpha	P68400	CSK21_HUMAN	Homo sapiens	4	0.7015
Dihydrofolate reductase	P22906	DYR_CANAX	Candida albicans	4	0.7014

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