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Calophyllolide

Family: Plantae - Sapotaceae
Kingdom: Plantae
Class: Xanthone

Canonical Smiles	C/C=C(/C(=O)c1c(OC)c2C=CC(Oc2c2c1oc(=O)cc2c1ccccc1)(C)C)\C
InChI	InChI=1S/C26H24O5/c1-6-15(2)22(28)21-23(29-5)17-12-13-26(3,4)31-24(17)20-18(14-19(27)30-25(20)21)16-10-8-7-9-11-16/h6-14H,1-5H3/b15-6+
InChIKey	PMBLOLOJQZPEND-GIDUJCDVSA-N
Formula	C₂₆H₂₄O₅
HBA	5
HBD	0
MW	416.47
Rotatable Bonds	4
TPSA	65.74
LogP	5.8
Number Rings	4
Number Aromatic Rings	3
Heavy Atom Count	31
Formal Charge	0
Fraction CSP3	0.23
Exact Mass	416.16
Number of Lipinski Rule Violations	1

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Manilkara obovata	Sapotaceae	Plantae	362719

Showing of synonyms

Akosung E, Kenmogne SB, et al. (2021). Bioactive constituents from Manilkara obovata (Sabine & G.Don) J.H.Hemsl.. Natural product research,2021, 35(22), 4347-4356. [View] [PubMed]

Pubchem: 5281392

Cas: 548-27-6

Kegg Ligand: C09158

Chebi: 3328

Nmrshiftdb2: 60077593

CPRiL: 301213

SMILES: O1CC=Cc(c1c23)ccc3oc(=O)cc2-c4ccccc4

Level: 1

Mol. Weight: 416.47 g/mol

SMILES: O1CC=Cc(c1c23)ccc2oc(=O)cc3

Level: 0

Mol. Weight: 416.47 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 416.47 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -4.72
Human Oral Bioavailability 20%: Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.66
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -1.83

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Penetrable
Fraction Unbound (Human): 1.71
Plasma Protein Binding: 79.67
Steady State Volume of Distribution: -

Metabolism

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

Excretion

Clearance: 3.21
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: 1.84
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Toxic
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 0.62
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 7.32
Micronucleos: Toxic
NR-AhR: Toxic
NR-AR: Safe
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: -43.24
Rat (Acute): 3.5
Rat (Chronic Oral): 1.82
Fathead Minnow: 6.07
Respiratory Disease: Toxic
Skin Sensitisation: Safe
SR-ARE: Toxic
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Toxic
SR-p53: Safe

General Properties

Boiling Point: 502.55
Hydration Free Energy: -3.83
Log(D) at pH=7.4: 4.02
Log(P): 5.18
Log S: -6.52
Log(Vapor Pressure): -8.33
Melting Point: 175.58
pKa Acid: 7.87
pKa Basic: 3.33

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	3	0.9667
cGMP-specific 3',5'-cyclic phosphodiesterase	O76074	PDE5A_HUMAN	Homo sapiens	3	0.9206
Peptidyl-prolyl cis-trans isomerase FKBP1A	P62942	FKB1A_HUMAN	Homo sapiens	3	0.8927
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.8648
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.8540
HTH-type transcriptional regulator QacR	P0A0N3	QACR_STAAM	Staphylococcus aureus	3	0.8431
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform	O02697	PK3CG_PIG	Sus scrofa	3	0.8412
Glycogen phosphorylase, muscle form	P00489	PYGM_RABIT	Oryctolagus cuniculus	3	0.8340
Proto-oncogene tyrosine-protein kinase Src	P00523	SRC_CHICK	Gallus gallus	3	0.7867
Fibroblast growth factor receptor 1	P11362	FGFR1_HUMAN	Homo sapiens	3	0.7863
Tyrosine-protein kinase Lck	P06239	LCK_HUMAN	Homo sapiens	3	0.7847
Lactoylglutathione lyase	Q9CPU0	LGUL_MOUSE	Mus musculus	2	0.7845
Progesterone receptor	P06401	PRGR_HUMAN	Homo sapiens	3	0.7740
Serine/threonine-protein kinase pim-1	P11309	PIM1_HUMAN	Homo sapiens	3	0.7676
HTH-type transcriptional regulator QacR	P0A0N4	QACR_STAAU	Staphylococcus aureus	3	0.7633
Pentaerythritol tetranitrate reductase	P71278	P71278_ENTCL	Enterobacter cloacae	2	0.7485
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7446
Bromodomain adjacent to zinc finger domain protein 2B	Q9UIF8	BAZ2B_HUMAN	Homo sapiens	2	0.7415
Gag-Pol polyprotein	P03367	POL_HV1BR	Human immunodeficiency virus type 1 group M subtype B	4	0.7408
Protein ppBat	Q8A8A4	Q8A8A4_BACTN	Bacteroides thetaiotaomicron VPI-5482	2	0.7392
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7351
Polymerase acidic protein	C3W5S0	C3W5S0_I09A0	Influenza A virus	2	0.7318
3-alpha-hydroxysteroid dehydrogenase	P23457	DIDH_RAT	Rattus norvegicus	2	0.7279
Pentaerythritol tetranitrate reductase	P71278	P71278_ENTCL	Enterobacter cloacae	2	0.7264
Mycocyclosin synthase	P9WPP7	CP121_MYCTU	Mycobacterium tuberculosis	3	0.7208
TDP-4-oxo-6-deoxy-alpha-D-glucose-3,4-oxoisomerase	Q6T1W8	FDTA_ANETH	Aneurinibacillus thermoaerophilus	3	0.7123
Ras-related protein Ral-B	P11234	RALB_HUMAN	Homo sapiens	2	0.7120
Nuclear receptor subfamily 4immunitygroup A member 1	P22736	NR4A1_HUMAN	Homo sapiens	2	0.7060
Neuropilin-1	O14786	NRP1_HUMAN	Homo sapiens	3	0.7033
CCA-adding enzyme	O28126	CCA_ARCFU	Archaeoglobus fulgidus	2	0.7026
Methionine aminopeptidase	P0AE18	MAP1_ECOLI	Escherichia coli	2	0.7008
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.7007

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