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Rhamnitrin

Family: Plantae - Sapotaceae
Kingdom: Plantae
Class: Flavonoid
- Subclass: Flavone

Canonical Smiles	COc1cc(O)c2c(c1)oc(c(c2=O)O[C@H]1OC(C)[C@H](C([C@H]1O)O)O)c1ccc(c(c1)O)O
InChI	InChI=1S/C22H22O11/c1-8-16(26)18(28)19(29)22(31-8)33-21-17(27)15-13(25)6-10(30-2)7-14(15)32-20(21)9-3-4-11(23)12(24)5-9/h3-8,16,18-19,22-26,28-29H,1-2H3/t8?,16-,18?,19-,22-/m1/s1
InChIKey	LOMXQCXSNSCLNP-FOOXGEMHSA-N
Formula	C₂₂H₂₂O₁₁
HBA	11
HBD	6
MW	462.41
Rotatable Bonds	4
TPSA	179.28
LogP	0.79
Number Rings	4
Number Aromatic Rings	3
Heavy Atom Count	33
Formal Charge	0
Fraction CSP3	0.32
Exact Mass	462.12
Number of Lipinski Rule Violations	2

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Synsepalum zenkeri	Sapotaceae	Plantae	233754

Showing of synonyms

Kuete V, Ngnintedo D, et al. (2018). Cytotoxicity of seputhecarpan D, thonningiol and 12 other phytochemicals from African flora towards human carcinoma cells.. BMC complementary and alternative medicine,2018, 18(1), 36. [View] [PubMed]

No compound-protein relationship available.

SMILES: c1cccc(c12)oc(-c3ccccc3)c(c2=O)OC4CCCCO4

Level: 2

Mol. Weight: 462.41 g/mol

SMILES: c1cccc(c12)occ(c2=O)OC3CCCCO3

Level: 1

Mol. Weight: 462.41 g/mol

SMILES: c1cccc(c12)oc(cc2=O)-c3ccccc3

Level: 1

Mol. Weight: 462.41 g/mol

SMILES: c1cccc(c12)occc2=O

Level: 0

Mol. Weight: 462.41 g/mol

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 462.41 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 462.41 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -6.5
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Non-Absorbed
Madin-Darby Canine Kidney: -5.260
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: 0.52

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 1.040
Plasma Protein Binding: 78.82
Steady State Volume of Distribution: -

Metabolism

Breast Cancer Resistance Protein: Non-Inhibitor
CYP 1A2 Inhibitor: Non-Inhibitor
CYP 1A2 Substrate: Non-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: 12.400
Organic Cation Transporter 2: Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Toxic
Avian: Safe
Bee: Safe
Bioconcentration Factor: -1.130
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Safe
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 1.090
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 5.300
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: Safe
T. Pyriformis: -109.560
Rat (Acute): 2.420
Rat (Chronic Oral): 3.600
Fathead Minnow: 4.230
Respiratory Disease: Safe
Skin Sensitisation: Safe
SR-ARE: Toxic
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Safe
SR-p53: Safe

General Properties

Boiling Point: 577.180
Hydration Free Energy: -4.030
Log(D) at pH=7.4: 1.300
Log(P): 1.34
Log S: -4.77
Log(Vapor Pressure): -10.15
Melting Point: 198.87
pKa Acid: 6.18
pKa Basic: 4.75

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	3	0.9791
Ribosomal small subunit pseudouridine synthase A	P0AA43	RSUA_ECOLI	Escherichia coli	3	0.9401
HTH-type transcriptional regulator TtgR	Q9AIU0	TTGR_PSEPT	Pseudomonas putida	4	0.9014
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.8996
Bromodomain-containing protein 2	P25440	BRD2_HUMAN	Homo sapiens	3	0.8920
Putative protease I	Q8A8A4	Q8A8A4_BACTN	Bacteroides thetaiotaomicron	3	0.8773
Serpin domain-containing protein	H0ZQY2	H0ZQY2_TAEGU	Taeniopygia guttata	3	0.8452
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8313
Major pollen allergen Bet v 1-A	P15494	BEV1A_BETPN	Betula pendula	3	0.8300
ATP synthase subunit alpha, mitochondrial	P19483	ATPA_BOVIN	Bos taurus	3	0.8269
Carbonyl reductase [NADPH] 1	P16152	CBR1_HUMAN	Homo sapiens	3	0.8153
Flavin reductase (NADPH)	P30043	BLVRB_HUMAN	Homo sapiens	3	0.8091
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8076
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.8002
Chloramphenicol 3-O phosphotransferase	Q56148	CPT_STRVP	Streptomyces venezuelae	4	0.7968
rRNA N-glycosylase	D9J2T9	D9J2T9_MOMBA	Momordica balsamina	3	0.7908
NAD(P)H-hydrate epimerase	Q8K4Z3	NNRE_MOUSE	Mus musculus	3	0.7876
Peptidyl-prolyl cis-trans isomerase FKBP1A	P62942	FKB1A_HUMAN	Homo sapiens	3	0.7841
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	3	0.7795
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7792
Rhodopsin kinase GRK1	P28327	GRK1_BOVIN	Bos taurus	3	0.7781
Bromodomain adjacent to zinc finger domain protein 2B	Q9UIF8	BAZ2B_HUMAN	Homo sapiens	3	0.7746
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.7719
Polyprotein	Q80J95	Q80J95_9CALI	Murine norovirus 1	3	0.7710
Endoplasmin	P41148	ENPL_CANLF	Canis lupus familiaris	4	0.7680
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.7678
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7627
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7602
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7554
Botulinum neurotoxin type A	P0DPI0	BXA1_CLOBO	Clostridium botulinum	3	0.7550
Genome polyprotein	O92972	POLG_HCVJ4	Hepatitis C virus genotype 1b	3	0.7485
Flavin-dependent monooxygenase	Q93L51	TETX_BACT4	Bacteroides thetaiotaomicron	3	0.7480
HTH-type transcriptional regulator TtgR	Q9AIU0	TTGR_PSEPT	Pseudomonas putida	3	0.7403
Mitogen-activated protein kinase 1	P28482	MK01_HUMAN	Homo sapiens	3	0.7392
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.7337
Leucoanthocyanidin dioxygenase	Q96323	LDOX_ARATH	Arabidopsis thaliana	5	0.7323
Phosphoenolpyruvate carboxykinase [GTP]	A5TYT6	PCKG_MYCTA	Mycobacterium tuberculosis	3	0.7293
Polymerase acidic protein	C3W5S0	C3W5S0_I09A0	Influenza A virus	2	0.7291
WxcM-like protein	Q12KT8	Q12KT8_SHEDO	Shewanella denitrificans	3	0.7230
Phosphoenolpyruvate carboxykinase [GTP]	P9WIH3	PCKG_MYCTU	Mycobacterium tuberculosis	3	0.7212
Beta-galactoside-specific lectin 4	Q6ITZ3	ML4_VISAL	Viscum album	2	0.7189
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7184
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.7162
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7159
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.7156
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	3	0.7130
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7129
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	2	0.7125
Avidin	P02701	AVID_CHICK	Gallus gallus	3	0.7080
Gag-Pol polyprotein	P05896	POL_SIVM1	Simian immunodeficiency virus	3	0.7076
3-phosphoinositide-dependent protein kinase 1	O15530	PDPK1_HUMAN	Homo sapiens	3	0.7065
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	Q05603	COBT_SALTY	Salmonella typhimurium	2	0.7061
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7056
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	2	0.7031
DNA-directed DNA polymerase	Q38087	DPOL_BPR69	Escherichia phage RB69	2	0.7028

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