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Cinchonain B

Family: Plantae - Meliaceae
Kingdom: Plantae
Class: Flavonoid
- Subclass: Flavonolignan

Canonical Smiles	O=C1Oc2cc(O)c3c(c2[C@@H](C1)c1ccc(c(c1)O)O)O[C@@H]([C@@H](C3)O)c1ccc(c(c1)O)O
InChI	InChI=1S/C24H20O9/c25-14-3-1-10(5-17(14)28)12-8-21(31)32-20-9-16(27)13-7-19(30)23(33-24(13)22(12)20)11-2-4-15(26)18(29)6-11/h1-6,9,12,19,23,25-30H,7-8H2/t12-,19+,23+/m0/s1
InChIKey	LKCOZWLUAKSRQM-IBUUURQNSA-N
Formula	C₂₄H₂₀O₉
HBA	9
HBD	6
MW	452.42
Rotatable Bonds	2
TPSA	156.91
LogP	2.69
Number Rings	5
Number Aromatic Rings	3
Heavy Atom Count	33
Formal Charge	0
Fraction CSP3	0.21
Exact Mass	452.11
Number of Lipinski Rule Violations	1

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Trichilia gilgiana	Meliaceae	Plantae	2709000

Showing of synonyms

Kowa TK, Tchokouaha LRY, et al. (2020). Antileishmanial and cytotoxic activities of a new limonoid and a new phenyl alkene from the stem bark of Trichilia gilgiana (Meliaceae).. Natural product research,2020, 34(22), 3182-3188. [View] [PubMed]

Pubchem: 10456516

Cas: 85022-69-1

Zinc: ZINC000005838202

Nmrshiftdb2: 70128231

Chembl: CHEMBL401058

Comptox: DTXSID00440220

No compound-protein relationship available.

SMILES: c1ccccc1C(O2)CCc(c2c34)ccc3OC(=O)CC4c5ccccc5

Level: 2

Mol. Weight: 452.42 g/mol

SMILES: O1CCCc(c1c23)ccc2OC(=O)CC3c4ccccc4

Level: 1

Mol. Weight: 452.42 g/mol

SMILES: C1CC(=O)Oc2ccc(c3c12)CCC(O3)c4ccccc4

Level: 1

Mol. Weight: 452.42 g/mol

SMILES: O1CCCc(c1c23)ccc2OC(=O)CC3

Level: 0

Mol. Weight: 452.42 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 452.42 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -6.97
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -5.13
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Inhibitor
P-Glycoprotein Substrate: Substrate
Skin Permeability: -0.07

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.99
Plasma Protein Binding: 87.18
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: Non-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: 12.29
Organic Cation Transporter 2: Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: -0.3
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Toxic
Eye Corrosion: Safe
Eye Irritation: Toxic
Maximum Tolerated Dose: 1.26
Liver Injury II: Toxic
hERG Blockers: Toxic
Daphnia Maga: 5.33
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: -155.2
Rat (Acute): 2.42
Rat (Chronic Oral): 3.32
Fathead Minnow: 4.62
Respiratory Disease: Toxic
Skin Sensitisation: Toxic
SR-ARE: Safe
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Toxic
SR-p53: Safe

General Properties

Boiling Point: 605.81
Hydration Free Energy: -3.71
Log(D) at pH=7.4: 1.59
Log(P): 0.98
Log S: -3.71
Log(Vapor Pressure): -11.73
Melting Point: 284.23
pKa Acid: 6.36
pKa Basic: 6.42

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Multidrug-efflux transporter 1 regulator	P39075	BMRR_BACSU	Bacillus subtilis	3	0.9607
Homoserine dehydrogenase	P31116	DHOM_YEAST	Saccharomyces cerevisiae	4	0.9283
Protease	O38896	O38896_9HIV1	Human immunodeficiency virus 1	3	0.9043
Chitinase	Q54276	Q54276_SERMA	Serratia marcescens	3	0.9028
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha	Q04631	FNTA_RAT	Rattus norvegicus	3	0.8944
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.8893
Acetylcholinesterase	P21836	ACES_MOUSE	Mus musculus	3	0.8839
Thymidylate synthase	P00469	TYSY_LACCA	Lacticaseibacillus casei	3	0.8835
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.8520
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.8373
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8318
Nuclear receptor subfamily 4immunitygroup A member 1	P22736	NR4A1_HUMAN	Homo sapiens	3	0.8218
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8202
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha	Q4WP27	Q4WP27_ASPFU	Aspergillus fumigatus	3	0.8170
Phenylalanine-4-hydroxylase	P00439	PH4H_HUMAN	Homo sapiens	4	0.8103
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	Q05603	COBT_SALTY	Salmonella typhimurium	3	0.8086
rRNA N-glycosylase	D9J2T9	D9J2T9_MOMBA	Momordica balsamina	3	0.8073
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	3	0.8055
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.8022
HTH-type transcriptional regulator QacR	P0A0N3	QACR_STAAM	Staphylococcus aureus	3	0.7976
Annexin A5	P08758	ANXA5_HUMAN	Homo sapiens	3	0.7962
Aldos-2-ulose dehydratase	P84193	AUD_PHACH	Phanerodontia chrysosporium	3	0.7952
Peptidyl-prolyl cis-trans isomerase FKBP1A	P62942	FKB1A_HUMAN	Homo sapiens	3	0.7894
NAD-capped RNA hydrolase NudC	P32664	NUDC_ECOLI	Escherichia coli	3	0.7847
Mitogen-activated protein kinase 14	Q16539	MK14_HUMAN	Homo sapiens	3	0.7808
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7802
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.7786
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.7734
Proliferating cell nuclear antigen	P12004	PCNA_HUMAN	Homo sapiens	3	0.7733
NAD(P)H-hydrate epimerase	Q8K4Z3	NNRE_MOUSE	Mus musculus	3	0.7685
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7672
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	4	0.7658
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7646
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.7559
Nitric oxide synthase oxygenase	O34453	NOSO_BACSU	Bacillus subtilis	4	0.7550
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7539
HTH-type transcriptional regulator QacR	P0A0N4	QACR_STAAU	Staphylococcus aureus	3	0.7533
Tyrosine-protein kinase JAK2	O60674	JAK2_HUMAN	Homo sapiens	3	0.7531
Vascular endothelial growth factor receptor 2	P35968	VGFR2_HUMAN	Homo sapiens	3	0.7526
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7497
Polyribonucleotide nucleotidyltransferase	A7ZS61	PNP_ECO24	Escherichia coli O139:H28	3	0.7471
Ephrin type-B receptor 4	P54760	EPHB4_HUMAN	Homo sapiens	3	0.7450
S-adenosylmethionine decarboxylase proenzyme	P17707	DCAM_HUMAN	Homo sapiens	3	0.7377
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	4	0.7360
Mycocyclosin synthase	P9WPP7	CP121_MYCTU	Mycobacterium tuberculosis	3	0.7350
Genome polyprotein	Q2YHF0	POLG_DEN4T	Dengue virus type 4	3	0.7268
N-terminal acetyltransferase A complex subunit NAT1	P12945	NAT1_YEAST	Saccharomyces cerevisiae	2	0.7250
Bifunctional dihydrofolate reductase-thymidylate synthase	P13922	DRTS_PLAFK	Plasmodium falciparum	3	0.7249
Riboflavin synthase	P0AFU8	RISA_ECOLI	Escherichia coli	4	0.7231
Oxygenase	Q194P4	Q194P4_STRAA	Streptomyces argillaceus	3	0.7229
Nodulin-13	P93330	NOD13_MEDTR	Medicago truncatula	3	0.7228
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.7208
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.7170
Transcriptional regulator, PadR-like family	A2RI36	A2RI36_LACLM	Lactococcus lactis subsp. cremoris	3	0.7163
Regucalcin	Q64374	RGN_MOUSE	Mus musculus	3	0.7159
cGMP-dependent 3',5'-cyclic phosphodiesterase	O00408	PDE2A_HUMAN	Homo sapiens	3	0.7156
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7148
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.7146
NAD(P)H dehydrogenase [quinone] 1	P15559	NQO1_HUMAN	Homo sapiens	4	0.7144
Collagenase 3	P45452	MMP13_HUMAN	Homo sapiens	3	0.7121
Cytosolic purine 5'-nucleotidase	P49902	5NTC_HUMAN	Homo sapiens	2	0.7111
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha	Q04631	FNTA_RAT	Rattus norvegicus	3	0.7106
cGMP-dependent protein kinase 1	Q13976	KGP1_HUMAN	Homo sapiens	3	0.7098
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	3	0.7094
Proton-gated ion channel	Q7NDN8	GLIC_GLOVI	Gloeobacter violaceus	3	0.7088
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7077
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	3	0.7063
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	3	0.7052
Lactoylglutathione lyase	Q9CPU0	LGUL_MOUSE	Mus musculus	2	0.7036
Vitamin D-binding protein	P02774	VTDB_HUMAN	Homo sapiens	2	0.7035
Serine/threonine-protein kinase 24	Q9Y6E0	STK24_HUMAN	Homo sapiens	4	0.7033
Flavin-dependent monooxygenase	Q93L51	TETX_BACT4	Bacteroides thetaiotaomicron	3	0.7033
Acetolactate synthase, chloroplastic	P17597	ILVB_ARATH	Arabidopsis thaliana	3	0.7019
5-methyltetrahydropteroyltriglutamate--homocysteine methyltransferase 1	O50008	METE1_ARATH	Arabidopsis thaliana	2	0.7004
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7001

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