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Garcimultiflorone E

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

Canonical Smiles	CC(=CC[C@]12C(=O)/C(=C(\c3ccc(c(c3)O)O)/O)/C(=O)[C@@](C1=O)(C[C@H](C(=C)C)CC(C(=C)C)O)C[C@H](C2(C)C)CC=C(C)C)C
InChI	InChI=1S/C38H50O7/c1-21(2)11-13-27-20-37(19-26(23(5)6)18-29(40)24(7)8)33(43)31(32(42)25-12-14-28(39)30(41)17-25)34(44)38(35(37)45,36(27,9)10)16-15-22(3)4/h11-12,14-15,17,26-27,29,39-42H,5,7,13,16,18-20H2,1-4,6,8-10H3/b32-31+/t26-,27-,29?,37-,38+/m1/s1
InChIKey	ISSDTQKSAPGZMB-XJHKIBOXSA-N
Formula	C₃₈H₅₀O₇
HBA	7
HBD	4
MW	618.81
Rotatable Bonds	11
TPSA	132.13
LogP	7.73
Number Rings	3
Number Aromatic Rings	1
Heavy Atom Count	45
Formal Charge	0
Fraction CSP3	0.5
Exact Mass	618.36
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: 46919308

No compound-protein relationship available.

SMILES: C1CCC(C2=O)C(=O)C(C(=O)C12)=Cc3ccccc3

Level: 1

Mol. Weight: 618.81 g/mol

SMILES: C12C(=O)C(=C)C(=O)C(C1=O)CCC2

Level: 0

Mol. Weight: 618.81 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 618.81 g/mol

Cancer cell growth inhibitory

Absorption

Caco-2 (logPapp): -4.97
Human Oral Bioavailability 20%: Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.88
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Substrate
Skin Permeability: 3.98

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Penetrable
Fraction Unbound (Human): 1.04
Plasma Protein Binding: 112.28
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: Inhibitor
CYP 3A4 Substrate: Substrate
OATP1B1: Inhibitor
OATP1B3: Inhibitor

Excretion

Clearance: 9.88
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: -1.45
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 0.29
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 7.29
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: -10981.44
Rat (Acute): 3.41
Rat (Chronic Oral): 3.42
Fathead Minnow: 31.25
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: 371.8
Hydration Free Energy: -2.91
Log(D) at pH=7.4: 4.59
Log(P): 7.59
Log S: -6.44
Log(Vapor Pressure): -14.67
Melting Point: 169.09
pKa Acid: 6.74
pKa Basic: 1.79

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Probable NDP-rhamnosyltransferase	Q9ALM8	Q9ALM8_SACSN	Saccharopolyspora spinosa	3	0.8806
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.8617
NAD(P)H-hydrate epimerase	Q8K4Z3	NNRE_MOUSE	Mus musculus	3	0.8583
D-aminoacyl-tRNA deacylase	Q8IIS0	DTD_PLAF7	Plasmodium falciparum	3	0.8509
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1	P04191	AT2A1_RABIT	Oryctolagus cuniculus	3	0.8421
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8420
Thymidine phosphorylase	Q7CP66	TYPH_SALTY	Salmonella typhimurium	3	0.8406
Retinol-binding protein 1	P02696	RET1_RAT	Rattus norvegicus	3	0.8363
Carbonic anhydrase 4	Q64444	CAH4_MOUSE	Mus musculus	3	0.8332
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase	Q9TQS6	DHDH_MACFA	Macaca fascicularis	3	0.8326
rRNA N-glycosylase	D9J2T9	D9J2T9_MOMBA	Momordica balsamina	3	0.8298
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8296
Phenylalanine-4-hydroxylase	P00439	PH4H_HUMAN	Homo sapiens	3	0.8286
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.8222
Chitinase	Q54276	Q54276_SERMA	Serratia marcescens	3	0.8216
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.8207
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.8189
NAD-capped RNA hydrolase NudC	P32664	NUDC_ECOLI	Escherichia coli	3	0.8187
Carbonic anhydrase 1	P00915	CAH1_HUMAN	Homo sapiens	3	0.8150
Androgen receptor	P10275	ANDR_HUMAN	Homo sapiens	3	0.8129
Catechol O-methyltransferase	P21964	COMT_HUMAN	Homo sapiens	3	0.8079
Serpin domain-containing protein	H0ZQY2	H0ZQY2_TAEGU	Taeniopygia guttata	3	0.8078
Ferrochelatase, mitochondrial	P22830	HEMH_HUMAN	Homo sapiens	3	0.7979
Peptidyl-prolyl cis-trans isomerase FKBP1A	P62942	FKB1A_HUMAN	Homo sapiens	3	0.7961
LysR-type regulatory protein	Q7WT50	Q7WT50_9BURK	Burkholderia sp. DNT	3	0.7944
Prostaglandin F2a synthase	Q8I6L9	Q8I6L9_TRYCR	Trypanosoma cruzi	3	0.7871
Gastrotropin	Q6IMW5	Q6IMW5_DANRE	Danio rerio	3	0.7772
Ribonuclease J	H9CZL7	H9CZL7_DEIRD	Deinococcus radiodurans	3	0.7686
Lactoylglutathione lyase	Q9CPU0	LGUL_MOUSE	Mus musculus	2	0.7684
Retinol-binding protein 1	P09455	RET1_HUMAN	Homo sapiens	3	0.7660
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	2	0.7576
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7531
Androgen receptor	P10275	ANDR_HUMAN	Homo sapiens	3	0.7467
Purine nucleoside phosphorylase DeoD-type	P0ABP9	DEOD_ECO57	Escherichia coli O157:H7	3	0.7445
Retinol dehydratase	Q26490	Q26490_SPOFR	Spodoptera frugiperda	3	0.7430
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	Q05603	COBT_SALTY	Salmonella typhimurium	2	0.7360
Fibroblast growth factor receptor 2	P21802	FGFR2_HUMAN	Homo sapiens	3	0.7359
Aldo-keto reductase family 1 member C1	Q04828	AK1C1_HUMAN	Homo sapiens	2	0.7353
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7347
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1	P04191	AT2A1_RABIT	Oryctolagus cuniculus	3	0.7338
Camphor 5-monooxygenase	P00183	CPXA_PSEPU	Pseudomonas putida	3	0.7334
3-hydroxy-3-methylglutaryl-coenzyme A reductase	P13702	MVAA_PSEMV	Pseudomonas mevalonii	3	0.7313
Mitochondrial poly(A) polymerase	F1NBW0	F1NBW0_CHICK	Gallus gallus	2	0.7307
Bifunctional epoxide hydrolase 2	P34913	HYES_HUMAN	Homo sapiens	2	0.7296
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7294
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7282
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7270
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7263
MAP kinase-activated protein kinase 2	P49137	MAPK2_HUMAN	Homo sapiens	3	0.7254
Sulfotransferase 2A1	Q06520	ST2A1_HUMAN	Homo sapiens	3	0.7252
Sulfotransferase 2B1	O00204	ST2B1_HUMAN	Homo sapiens	3	0.7249
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	2	0.7220
CmeR	Q7B8P6	Q7B8P6_CAMJU	Campylobacter jejuni	2	0.7211
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	2	0.7200
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7199
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7188
3-hydroxyanthranilate 3,4-dioxygenase	Q1LCS4	3HAO_CUPMC	Cupriavidus metallidurans	2	0.7175
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7173
Flavoredoxin	Q72HI0	Q72HI0_THET2	Thermus thermophilus	2	0.7172
Rhodopsin	P02699	OPSD_BOVIN	Bos taurus	3	0.7144
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	3	0.7136
Histone deacetylase-like amidohydrolase	Q70I53	HDAH_ALCSD	Alcaligenes sp.)	2	0.7126
Histone deacetylase 8	Q9BY41	HDAC8_HUMAN	Homo sapiens	2	0.7112
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7108
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7104
NAD(P)H-hydrate epimerase	Q8K4Z3	NNRE_MOUSE	Mus musculus	3	0.7099
Corticosteroid-binding globulin	P08185	CBG_HUMAN	Homo sapiens	3	0.7098
cAMP-dependent protein kinase catalytic subunit alpha	P00517	KAPCA_BOVIN	Bos taurus	3	0.7098
Protein mono-ADP-ribosyltransferase PARP3	Q9Y6F1	PARP3_HUMAN	Homo sapiens	3	0.7089
Hypoxanthine phosphoribosyltransferase	Q4DRC4	Q4DRC4_TRYCC	Trypanosoma cruzi	3	0.7083
Avidin	P02701	AVID_CHICK	Gallus gallus	2	0.7063
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	Q05603	COBT_SALTY	Salmonella typhimurium	2	0.7052
Sulfotransferase 2A1	Q06520	ST2A1_HUMAN	Homo sapiens	3	0.7041
Formylmethanofuran--tetrahydromethanopterin formyltransferase	Q49610	FTR_METKA	Methanopyrus kandleri	3	0.7037
Cyclic GMP-AMP phosphodiesterase SMPDL3A	Q92484	ASM3A_HUMAN	Homo sapiens	2	0.7028
Protocatechuate 3,4-dioxygenase beta chain	P00437	PCXB_PSEPU	Pseudomonas putida	2	0.7028
Gentisate 1,2-dioxygenase	Q67FT0	Q67FT0_PSESE	Pseudaminobacter salicylatoxidans	2	0.7020
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7019
Acetolactate synthase, chloroplastic	P17597	ILVB_ARATH	Arabidopsis thaliana	2	0.7019

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