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Isojacareubin

Family: Plantae - Clusiaceae
Kingdom: Plantae
Class: Xanthone

Canonical Smiles	Oc1ccc2c(c1O)oc1c(c2=O)c(O)cc2c1C=CC(O2)(C)C
InChI	InChI=1S/C18H14O6/c1-18(2)6-5-8-12(24-18)7-11(20)13-14(21)9-3-4-10(19)15(22)17(9)23-16(8)13/h3-7,19-20,22H,1-2H3
InChIKey	FSTNFJKGRSHPBO-UHFFFAOYSA-N
Formula	C₁₈H₁₄O₆
HBA	6
HBD	3
MW	326.3
Rotatable Bonds	0
TPSA	100.13
LogP	3.25
Number Rings	4
Number Aromatic Rings	3
Heavy Atom Count	24
Formal Charge	0
Fraction CSP3	0.17
Exact Mass	326.08
Number of Lipinski Rule Violations	0

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Garcinia livingstonei	Clusiaceae	Plantae	469932

Showing of synonyms

Mulholland DA, Mwangi EM, et al. (2013). Non-toxic melanin production inhibitors from Garcinia livingstonei (Clusiaceae). Journal of ethnopharmacology, 2013, 149(2), 570–575. [View]

Pubchem: 9996463

Cas: 50597-93-8

Zinc: ZINC000014560090

Nmrshiftdb2: 60077532

Chembl: CHEMBL5426411

CPRiL: 109297

SMILES: C1=CCOc(cc2)c1c(c23)oc4c(c3=O)cccc4

Level: 0

Mol. Weight: 326.3 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -5.03
Human Oral Bioavailability 20%: Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.910
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -0.86

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 1.140
Plasma Protein Binding: 64.23
Steady State Volume of Distribution: -

Metabolism

Breast Cancer Resistance Protein: Inhibitor
CYP 1A2 Inhibitor: Inhibitor
CYP 1A2 Substrate: Non-Substrate
CYP 2C19 Inhibitor: Inhibitor
CYP 2C19 Substrate: Non-Substrate
CYP 2C9 Inhibitor: Inhibitor
CYP 2C9 Substrate: Substrate
CYP 2D6 Inhibitor: Inhibitor
CYP 2D6 Substrate: Non-Substrate
CYP 3A4 Inhibitor: Non-Inhibitor
CYP 3A4 Substrate: Non-Substrate
OATP1B1: Non-Inhibitor
OATP1B3: Non-Inhibitor

Excretion

Clearance: 5.810
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Toxic
Avian: Safe
Bee: Toxic
Bioconcentration Factor: 0.820
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Toxic
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 0.780
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 5.530
Micronucleos: Toxic
NR-AhR: Toxic
NR-AR: Safe
NR-AR-LBD: Safe
NR-Aromatase: Safe
NR-ER: Toxic
NR-ER-LBD: Safe
NR-GR: Toxic
NR-PPAR-gamma: Safe
NR-TR: Safe
T. Pyriformis: 3.950
Rat (Acute): 2.460
Rat (Chronic Oral): 2.910
Fathead Minnow: 4.630
Respiratory Disease: Toxic
Skin Sensitisation: Toxic
SR-ARE: Toxic
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Toxic
SR-p53: Safe

General Properties

Boiling Point: 475.050
Hydration Free Energy: -11.210
Log(D) at pH=7.4: 2.860
Log(P): 3.94
Log S: -4.69
Log(Vapor Pressure): -8.71
Melting Point: 280.93
pKa Acid: 6.53
pKa Basic: 5.09

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	3	0.9176
Neocarzinostatin	P0A3R9	NCZS_STRCZ	Streptomyces carzinostaticus	3	0.9051
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	3	0.8526
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.8517
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.8442
TetR family transcriptional regulator	Q58L87	Q58L87_MYCSM	Mycolicibacterium smegmatis	3	0.8129
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	F6MZ55	F6MZ55_9FIRM	Sporomusa ovata	3	0.8016
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.7912
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	3	0.7892
Protein ppBat	Q8A8A4	Q8A8A4_BACTN	Bacteroides thetaiotaomicron VPI-5482	3	0.7835
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	4	0.7776
Capsid protein	Q9WBP8	Q9WBP8_9VIRU	Adeno-associated virus - 1	3	0.7732
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7704
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	3	0.7669
MAP kinase-activated protein kinase 2	P49137	MAPK2_HUMAN	Homo sapiens	3	0.7600
Cytochrome P450 monooxygenase	Q5YNS8	Q5YNS8_NOCFA	Nocardia farcinica	3	0.7572
Vascular endothelial growth factor receptor 2	P35968	VGFR2_HUMAN	Homo sapiens	3	0.7449
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7441
Cytosolic purine 5'-nucleotidase	P49902	5NTC_HUMAN	Homo sapiens	2	0.7432
APH(2'')-Id	O68183	O68183_ENTCA	Enterococcus casseliflavus	4	0.7409
4-hydroxyphenylacetate 3-monooxygenase	Q8YHT7	Q8YHT7_BRUME	Brucella melitensis biotype 1	2	0.7373
Type II methyltransferase M.TaqI	P14385	MTTA_THEAQ	Thermus aquaticus	3	0.7355
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7217
ActVA 6 protein	Q53908	Q53908_STRCH	Streptomyces coelicolor	3	0.7192
ADP compounds hydrolase NudE	P45799	NUDE_ECOLI	Escherichia coli	3	0.7180
Retinaldehyde-binding protein 1	P12271	RLBP1_HUMAN	Homo sapiens	4	0.7132
Tyrosine-protein kinase JAK2	O60674	JAK2_HUMAN	Homo sapiens	3	0.7093
Vitamin D3 receptor	P13053	VDR_RAT	Rattus norvegicus	4	0.7069
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7053
Beta-galactosidase	P00722	BGAL_ECOLI	Escherichia coli	3	0.7006

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