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Xanthochymol

Family: Plantae - Guttiferae
Kingdom: Plantae
Class: Terpenoid
- Subclass: Sesquiterpene

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)CCC(=C)C)C[C@@H](C2(C)C)CC=C(C)C)C
InChI	InChI=1S/C38H50O6/c1-22(2)11-13-27(25(7)8)20-37-21-28(15-12-23(3)4)36(9,10)38(35(37)44,18-17-24(5)6)34(43)31(33(37)42)32(41)26-14-16-29(39)30(40)19-26/h12,14,16-17,19,27-28,39-41H,1,7,11,13,15,18,20-21H2,2-6,8-10H3/b32-31+/t27-,28+,37+,38-/m1/s1
InChIKey	TZZQZCIACNYHBG-OLPCVCRBSA-N
Formula	C₃₈H₅₀O₆
HBA	6
HBD	3
MW	602.81
Rotatable Bonds	11
TPSA	111.9
LogP	8.76
Number Rings	3
Number Aromatic Rings	1
Heavy Atom Count	44
Formal Charge	0
Fraction CSP3	0.5
Exact Mass	602.36
Number of Lipinski Rule Violations	2

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Garcinia ovalifolia	Guttiferae	Plantae	469935

Showing of synonyms

Gustafson KR, Blunt JW, et al. (1992). The guttiferones, HIV-inhibitory benzophenones from Symphonia globulifera, Garcinia livingstonei, Garcinia ovalifolia and Clusia rosea. Tetrahedron, 1992, 48(46), 10093-10192. [View]

Pubchem: 9938674

Nmrshiftdb2: 60030275

CPRiL: 214231

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

Level: 1

Mol. Weight: 602.81 g/mol

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

Level: 0

Mol. Weight: 602.81 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 602.81 g/mol

Anti-hiv

Absorption

Caco-2 (logPapp): -4.86
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: 2.0

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Penetrable
Fraction Unbound (Human): 1.24
Plasma Protein Binding: 115.71
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: Inhibitor

Excretion

Clearance: 7.51
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: -0.36
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 0.27
Liver Injury II: Toxic
hERG Blockers: Toxic
Daphnia Maga: 7.23
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: -7282.79
Rat (Acute): 3.05
Rat (Chronic Oral): 3.32
Fathead Minnow: 23.16
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: 407.32
Hydration Free Energy: -2.86
Log(D) at pH=7.4: 5.14
Log(P): 8.76
Log S: -6.81
Log(Vapor Pressure): -12.05
Melting Point: 153.94
pKa Acid: 6.97
pKa Basic: 2.51

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
D-aminoacyl-tRNA deacylase	Q8IIS0	DTD_PLAF7	Plasmodium falciparum	3	0.9364
Corticosteroid-binding globulin	P08185	CBG_HUMAN	Homo sapiens	3	0.9243
Type IV / VI secretion system DotU domain-containing protein	Q9KN50	Q9KN50_VIBCH	Vibrio cholerae serotype O1	3	0.9069
Carbonic anhydrase 1	P00915	CAH1_HUMAN	Homo sapiens	3	0.8971
Retinol-binding protein 1	P02696	RET1_RAT	Rattus norvegicus	3	0.8925
NAD-capped RNA hydrolase NudC	P32664	NUDC_ECOLI	Escherichia coli	3	0.8853
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase	Q9TQS6	DHDH_MACFA	Macaca fascicularis	3	0.8779
rRNA N-glycosylase	D9J2T9	D9J2T9_MOMBA	Momordica balsamina	3	0.8760
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.8641
DNA gyrase subunit A	P0AES5	GYRA_SHIFL	Shigella flexneri	3	0.8640
Prostaglandin F2a synthase	Q8I6L9	Q8I6L9_TRYCR	Trypanosoma cruzi	3	0.8635
NAD(P)H-hydrate epimerase	Q8K4Z3	NNRE_MOUSE	Mus musculus	3	0.8595
Coagulation factor X	P00742	FA10_HUMAN	Homo sapiens	3	0.8574
Serpin domain-containing protein	H0ZQY2	H0ZQY2_TAEGU	Taeniopygia guttata	3	0.8493
Biflaviolin synthase CYP158A1	Q9KZF5	C1581_STRCO	Streptomyces coelicolor / M145)	3	0.8432
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8427
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.8424
Phenylalanine-4-hydroxylase	P00439	PH4H_HUMAN	Homo sapiens	3	0.8371
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.8324
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8299
Chitinase	Q54276	Q54276_SERMA	Serratia marcescens	3	0.8283
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.8265
Thymidine phosphorylase	Q7CP66	TYPH_SALTY	Salmonella typhimurium	3	0.8247
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	3	0.8181
Catechol O-methyltransferase	P21964	COMT_HUMAN	Homo sapiens	3	0.8173
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.8140
Carbonic anhydrase 4	Q64444	CAH4_MOUSE	Mus musculus	3	0.8139
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.8111
Acetylcholinesterase	P21836	ACES_MOUSE	Mus musculus	2	0.8097
Mycinamicin III 3''-O-methyltransferase	Q49492	MYCF_MICGR	Micromonospora griseorubida	2	0.8075
LysR-type regulatory protein	Q7WT50	Q7WT50_9BURK	Burkholderia sp. DNT	3	0.7996
NAD(P)H-hydrate epimerase	Q8K4Z3	NNRE_MOUSE	Mus musculus	3	0.7930
prolyl oligopeptidase	Q9X6R4	Q9X6R4_AERCA	Aeromonas caviae	3	0.7915
Retinol dehydratase	Q26490	Q26490_SPOFR	Spodoptera frugiperda	3	0.7893
Peptidyl-prolyl cis-trans isomerase FKBP1A	P62942	FKB1A_HUMAN	Homo sapiens	3	0.7883
Alcohol dehydrogenase 1C	P00326	ADH1G_HUMAN	Homo sapiens	2	0.7862
Lactoylglutathione lyase	Q9CPU0	LGUL_MOUSE	Mus musculus	2	0.7849
MAP kinase-activated protein kinase 2	P49137	MAPK2_HUMAN	Homo sapiens	3	0.7826
Photosynthetic reaction center cytochrome c subunit	P07173	CYCR_BLAVI	Blastochloris viridis	2	0.7825
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7789
CmeR	Q7B8P6	Q7B8P6_CAMJU	Campylobacter jejuni	2	0.7722
Ribonuclease J	H9CZL7	H9CZL7_DEIRD	Deinococcus radiodurans	3	0.7719
Beta-lactoglobulin	P02754	LACB_BOVIN	Bos taurus	3	0.7710
Gag-Pol polyprotein	P05896	POL_SIVM1	Simian immunodeficiency virus	3	0.7689
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	2	0.7679
Bacteriorhodopsin	P02945	BACR_HALSA	Halobacterium salinarum	3	0.7644
Succinate dehydrogenase flavoprotein subunit	P0AC41	SDHA_ECOLI	Escherichia coli	3	0.7634
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7632
Cellular retinol-binding protein type II	Q8UVG6	Q8UVG6_DANRE	Danio rerio	3	0.7630
NADPH-dependent oxidoreductase 2-alkenal reductase	Q39172	AER_ARATH	Arabidopsis thaliana	3	0.7629
Pantothenate synthetase	P9WIL5	PANC_MYCTU	Mycobacterium tuberculosis	3	0.7607
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	2	0.7605
cAMP-dependent protein kinase catalytic subunit alpha	P00517	KAPCA_BOVIN	Bos taurus	3	0.7601
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7596
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7585
Protein BRASSINOSTEROID INSENSITIVE 1	O22476	BRI1_ARATH	Arabidopsis thaliana	3	0.7582
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	3	0.7581
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7576
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7553
3-alpha-hydroxysteroid dehydrogenase	P23457	DIDH_RAT	Rattus norvegicus	2	0.7531
Probable NDP-rhamnosyltransferase	Q9ALM8	Q9ALM8_SACSN	Saccharopolyspora spinosa	3	0.7517
Sulfotransferase 2B1	O00204	ST2B1_HUMAN	Homo sapiens	2	0.7517
Integrin alpha-L	P20701	ITAL_HUMAN	Homo sapiens	3	0.7505
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	2	0.7504
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	2	0.7502
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	Q05603	COBT_SALTY	Salmonella typhimurium	2	0.7491
Sodium-dependent dopamine transporter	Q7K4Y6	DAT_DROME	Drosophila melanogaster	2	0.7448
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7443
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial	Q0QF01	SDHA_PIG	Sus scrofa	3	0.7437
Succinate dehydrogenase flavoprotein subunit	P0AC41	SDHA_ECOLI	Escherichia coli	3	0.7420
Bifunctional epoxide hydrolase 2	P34913	HYES_HUMAN	Homo sapiens	2	0.7408
Fatty acid-binding protein 10-A, liver basic	Q9I8L5	FA10A_DANRE	Danio rerio	2	0.7379
Fibroblast growth factor receptor 2	P21802	FGFR2_HUMAN	Homo sapiens	3	0.7365
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7353
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.7352
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7349
17-beta-hydroxysteroid dehydrogenase type 1	P14061	DHB1_HUMAN	Homo sapiens	2	0.7347
3-hydroxy-3-methylglutaryl-coenzyme A reductase	P13702	MVAA_PSEMV	Pseudomonas mevalonii	3	0.7309
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7299
Aldo-keto reductase family 1 member C1	Q04828	AK1C1_HUMAN	Homo sapiens	2	0.7299
cGMP-dependent 3',5'-cyclic phosphodiesterase	O00408	PDE2A_HUMAN	Homo sapiens	3	0.7277
Tryptophan--tRNA ligase	Q9PIB4	SYW_CAMJE	Campylobacter jejuni subsp. jejuni serotype O:2	4	0.7266
Rhodopsin	P02699	OPSD_BOVIN	Bos taurus	3	0.7258
APH(2'')-Id	O68183	O68183_ENTCA	Enterococcus casseliflavus	3	0.7258
Deoxycytidine kinase	P27707	DCK_HUMAN	Homo sapiens	4	0.7254
Streptavidin	P22629	SAV_STRAV	Streptomyces avidinii	2	0.7250
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1	P04191	AT2A1_RABIT	Oryctolagus cuniculus	3	0.7236
Rhodopsin	P02699	OPSD_BOVIN	Bos taurus	2	0.7233
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta	P78356	PI42B_HUMAN	Homo sapiens	3	0.7227
4,4'-diapophytoene synthase	A9JQL9	CRTM_STAAU	Staphylococcus aureus	2	0.7216
Formylmethanofuran--tetrahydromethanopterin formyltransferase	Q49610	FTR_METKA	Methanopyrus kandleri	3	0.7216
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7215
Flavoredoxin	Q72HI0	Q72HI0_THET2	Thermus thermophilus	2	0.7194
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7190
Dipeptidyl peptidase 4	P27487	DPP4_HUMAN	Homo sapiens	2	0.7183
Ribosomal small subunit pseudouridine synthase A	P0AA43	RSUA_ECOLI	Escherichia coli	3	0.7179
Aldo-keto reductase family 1 member B1	P80276	ALDR_PIG	Sus scrofa	3	0.7178
17-beta-hydroxysteroid dehydrogenase type 1	P14061	DHB1_HUMAN	Homo sapiens	2	0.7174
Prostaglandin reductase 2	Q8N8N7	PTGR2_HUMAN	Homo sapiens	2	0.7160
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7145
Cytidine and deoxycytidylate deaminase zinc-binding region	Q82Y41	Q82Y41_NITEU	Nitrosomonas europaea	4	0.7136
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7132
Hypoxanthine phosphoribosyltransferase	Q4DRC4	Q4DRC4_TRYCC	Trypanosoma cruzi	3	0.7129
Protein mono-ADP-ribosyltransferase PARP3	Q9Y6F1	PARP3_HUMAN	Homo sapiens	3	0.7126
17-beta-hydroxysteroid dehydrogenase type 1	P14061	DHB1_HUMAN	Homo sapiens	2	0.7124
Abscisic acid receptor PYL2	O80992	PYL2_ARATH	Arabidopsis thaliana	2	0.7123
Cyclic GMP-AMP phosphodiesterase SMPDL3A	Q92484	ASM3A_HUMAN	Homo sapiens	2	0.7115
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7107
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	Q05603	COBT_SALTY	Salmonella typhimurium	2	0.7098
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	2	0.7071
Beta-1 adrenergic receptor	P07700	ADRB1_MELGA	Meleagris gallopavo	2	0.7069
prolyl oligopeptidase	Q9X6R4	Q9X6R4_AERCA	Aeromonas caviae	3	0.7068
Sulfotransferase 2B1	O00204	ST2B1_HUMAN	Homo sapiens	2	0.7064
Neocarzinostatin	P0A3R9	NCZS_STRCZ	Streptomyces carzinostaticus	2	0.7059
Toxoflavin degrading enzyme	E3SET7	E3SET7_PAEPO	Paenibacillus polymyxa	3	0.7047
Protocatechuate 3,4-dioxygenase beta chain	P00437	PCXB_PSEPU	Pseudomonas putida	2	0.7045
Acetolactate synthase, chloroplastic	P17597	ILVB_ARATH	Arabidopsis thaliana	2	0.7041
17-beta-hydroxysteroid dehydrogenase type 1	P14061	DHB1_HUMAN	Homo sapiens	2	0.7036
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	2	0.7036
Nuclear receptor subfamily 1 group I member 3	O35627	NR1I3_MOUSE	Mus musculus	2	0.7032
Tyrosine-protein kinase JAK2	O60674	JAK2_HUMAN	Homo sapiens	3	0.7032
Polyprotein	Q80J95	Q80J95_9CALI	Murine norovirus 1	4	0.7021
Vitamin D(3) 25-hydroxylase	C4B644	CPVDH_PSEAH	Pseudonocardia autotrophica	3	0.7016

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