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Garcinialiptone B

Family: Plantae - Clusiaceae
Kingdom: Plantae
Class: Phenolic
- Subclass: Benzophenone

Canonical Smiles	CC(=CC[C@@]12C(=O)C(=C3[C@](C1=O)(C[C@H]([C@@H](O3)C=C(C)C)C(=C)C)C[C@@H](C2(C)C)CC=C(C)C)C(=O)c1ccc(c(c1)O)O)C
InChI	InChI=1S/C38H48O6/c1-21(2)11-13-26-19-37-20-27(24(7)8)30(17-23(5)6)44-34(37)31(32(41)25-12-14-28(39)29(40)18-25)33(42)38(35(37)43,36(26,9)10)16-15-22(3)4/h11-12,14-15,17-18,26-27,30,39-40H,7,13,16,19-20H2,1-6,8-10H3/t26-,27-,30-,37+,38+/m0/s1
InChIKey	AFHKVDYTQYGRHC-JVFVNDAQSA-N
Formula	C₃₈H₄₈O₆
HBA	6
HBD	2
MW	600.8
Rotatable Bonds	8
TPSA	100.9
LogP	8.37
Number Rings	4
Number Aromatic Rings	1
Heavy Atom Count	44
Formal Charge	0
Fraction CSP3	0.5
Exact Mass	600.35
Number of Lipinski Rule Violations	2

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Garcinia preussii	Clusiaceae	Plantae	58227

Showing of synonyms

Biloa Messi B, Ho R, et al. (2014). Isolation and biological activity of compounds from Garcinia preussii.. Pharmaceutical biology,2014, 52(6), 706-711. [View] [PubMed]

Pubchem: 46184557

Cas: 1220854-30-7

Zinc: ZINC000049777509

Nmrshiftdb2: 60081802

Chembl: CHEMBL1077025

No compound-protein relationship available.

SMILES: C1CCC(C2=O)C(=O)C(=C(C123)OCCC3)C(=O)c4ccccc4

Level: 1

Mol. Weight: 600.8 g/mol

SMILES: C1CCC(C2=O)C(=O)C=C(C123)OCCC3

Level: 0

Mol. Weight: 600.8 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 600.8 g/mol

Cancer cell growth inhibitory

Absorption

Caco-2 (logPapp): -4.79
Human Oral Bioavailability 20%: Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.85
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: 3.67

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Penetrable
Fraction Unbound (Human): 1.28
Plasma Protein Binding: 111.91
Steady State Volume of Distribution: -

Metabolism

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

Excretion

Clearance: 8.49
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: 0.11
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: -0.05
Liver Injury II: Toxic
hERG Blockers: Toxic
Daphnia Maga: 7.45
Micronucleos: Toxic
NR-AhR: Safe
NR-AR: Toxic
NR-AR-LBD: Safe
NR-Aromatase: Safe
NR-ER: Safe
NR-ER-LBD: Safe
NR-GR: Toxic
NR-PPAR-gamma: Safe
NR-TR: Safe
T. Pyriformis: -9792.43
Rat (Acute): 2.58
Rat (Chronic Oral): 3.32
Fathead Minnow: 29.12
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: 365.61
Hydration Free Energy: -2.91
Log(D) at pH=7.4: 5.56
Log(P): 9.28
Log S: -7.43
Log(Vapor Pressure): -14.47
Melting Point: 202.86
pKa Acid: 6.75
pKa Basic: 2.27

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Lactoylglutathione lyase	Q9CPU0	LGUL_MOUSE	Mus musculus	3	0.8850
Retinol-binding protein 1	P02696	RET1_RAT	Rattus norvegicus	3	0.8674
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8412
NAD(P)H-hydrate epimerase	Q8K4Z3	NNRE_MOUSE	Mus musculus	3	0.8391
Retinol dehydratase	Q26490	Q26490_SPOFR	Spodoptera frugiperda	3	0.8341
Carbonic anhydrase 1	P00915	CAH1_HUMAN	Homo sapiens	3	0.8320
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8293
D-aminoacyl-tRNA deacylase	Q8IIS0	DTD_PLAF7	Plasmodium falciparum	3	0.8208
Mycinamicin III 3''-O-methyltransferase	Q49492	MYCF_MICGR	Micromonospora griseorubida	2	0.8171
Retinol-binding protein 2	P50120	RET2_HUMAN	Homo sapiens	3	0.8063
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase	Q9TQS6	DHDH_MACFA	Macaca fascicularis	3	0.7910
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7904
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7817
Catechol O-methyltransferase	P21964	COMT_HUMAN	Homo sapiens	3	0.7789
NAD(P)H-hydrate epimerase	Q8K4Z3	NNRE_MOUSE	Mus musculus	3	0.7742
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7689
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	2	0.7682
Streptavidin	P22629	SAV_STRAV	Streptomyces avidinii	2	0.7664
CmeR	Q7B8P6	Q7B8P6_CAMJU	Campylobacter jejuni	2	0.7627
Lethal(3)malignant brain tumor-like protein 1	Q9Y468	LMBL1_HUMAN	Homo sapiens	3	0.7564
Peptidyl-prolyl cis-trans isomerase FKBP1A	P62942	FKB1A_HUMAN	Homo sapiens	2	0.7558
Acetylcholinesterase	P21836	ACES_MOUSE	Mus musculus	2	0.7544
Vitamin D(3) 25-hydroxylase	C4B644	CPVDH_PSEAH	Pseudonocardia autotrophica	3	0.7514
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	2	0.7487
Probable NDP-rhamnosyltransferase	Q9ALM8	Q9ALM8_SACSN	Saccharopolyspora spinosa	2	0.7477
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7470
Pantothenate synthetase	P9WIL5	PANC_MYCTU	Mycobacterium tuberculosis	3	0.7427
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7373
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	Q05603	COBT_SALTY	Salmonella typhimurium	2	0.7354
LysR-type regulatory protein	Q7WT50	Q7WT50_9BURK	Burkholderia sp. DNT	3	0.7340
Genome polyprotein	P26663	POLG_HCVBK	Hepatitis C virus genotype 1b	4	0.7311
Retinol-binding protein 4	P18902	RET4_BOVIN	Bos taurus	3	0.7301
Photosynthetic reaction center cytochrome c subunit	P07173	CYCR_BLAVI	Blastochloris viridis	2	0.7293
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7225
Streptavidin	P22629	SAV_STRAV	Streptomyces avidinii	2	0.7210
Pentaerythritol tetranitrate reductase	P71278	P71278_ENTCL	Enterobacter cloacae	2	0.7188
prolyl oligopeptidase	Q9X6R4	Q9X6R4_AERCA	Aeromonas caviae	3	0.7179
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7163
Hypoxanthine phosphoribosyltransferase	Q4DRC4	Q4DRC4_TRYCC	Trypanosoma cruzi	3	0.7147
Aldo-keto reductase family 1 member C1	Q04828	AK1C1_HUMAN	Homo sapiens	2	0.7123
Peptidyl-prolyl cis-trans isomerase FKBP1A	P62942	FKB1A_HUMAN	Homo sapiens	3	0.7118
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7085
rRNA N-glycosylase	D9J2T9	D9J2T9_MOMBA	Momordica balsamina	3	0.7040
Bifunctional epoxide hydrolase 2	P34913	HYES_HUMAN	Homo sapiens	2	0.7012
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7008
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7002
Ribosomal small subunit pseudouridine synthase A	P0AA43	RSUA_ECOLI	Escherichia coli	3	0.7001

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