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Calaustralin

Family: Plantae - Sapotaceae
Kingdom: Plantae
Class: Coumarin
- Subclass: 4-Phenylcoumarin

Canonical Smiles	CC(=CCc1c2O[C@H](C)[C@H](C(=O)c2c(c2c1oc(=O)cc2c1ccccc1)O)C)C
InChI	InChI=1S/C25H24O5/c1-13(2)10-11-17-24-20(18(12-19(26)30-24)16-8-6-5-7-9-16)23(28)21-22(27)14(3)15(4)29-25(17)21/h5-10,12,14-15,28H,11H2,1-4H3/t14-,15-/m1/s1
InChIKey	LCHRCBXGRPWRBG-HUUCEWRRSA-N
Formula	C₂₅H₂₄O₅
HBA	5
HBD	1
MW	404.46
Rotatable Bonds	3
TPSA	76.74
LogP	5.27
Number Rings	4
Number Aromatic Rings	3
Heavy Atom Count	30
Formal Charge	0
Fraction CSP3	0.28
Exact Mass	404.16
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: 21579151

Zinc: ZINC000013382520

Nmrshiftdb2: 70017989

No compound-protein relationship available.

SMILES: O1CCC(=O)c(c2)c1cc(c23)oc(=O)cc3-c4ccccc4

Level: 1

Mol. Weight: 404.46 g/mol

SMILES: O=C1CCOc(c12)cc3c(c2)ccc(=O)o3

Level: 0

Mol. Weight: 404.46 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 404.46 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -4.78
Human Oral Bioavailability 20%: Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.71
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -1.75

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 1.49
Plasma Protein Binding: 97.69
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: 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: 5.66
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Toxic
Avian: Safe
Bee: Toxic
Bioconcentration Factor: 1.56
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: Toxic
Daphnia Maga: 6.4
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: -26.66
Rat (Acute): 3.31
Rat (Chronic Oral): 1.83
Fathead Minnow: 5.35
Respiratory Disease: Toxic
Skin Sensitisation: Safe
SR-ARE: Toxic
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Toxic
SR-p53: Toxic

General Properties

Boiling Point: 498.12
Hydration Free Energy: -4.82
Log(D) at pH=7.4: 3.83
Log(P): 5.52
Log S: -6.01
Log(Vapor Pressure): -9.48
Melting Point: 179.94
pKa Acid: 6.8
pKa Basic: 5.17

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Glycogen phosphorylase, muscle form	P00489	PYGM_RABIT	Oryctolagus cuniculus	3	0.9592
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.8919
Mitogen-activated protein kinase 14	Q16539	MK14_HUMAN	Homo sapiens	3	0.8867
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.8686
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.8607
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.8259
Aurora kinase A	O14965	AURKA_HUMAN	Homo sapiens	3	0.8255
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.8238
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.8198
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.8065
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	3	0.8003
Tyrosine-protein kinase Lck	P06239	LCK_HUMAN	Homo sapiens	3	0.7921
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7897
prolyl oligopeptidase	Q9X6R4	Q9X6R4_AERCA	Aeromonas caviae	3	0.7874
Aldo-keto reductase family 1 member B10	O60218	AK1BA_HUMAN	Homo sapiens	3	0.7802
Serine/threonine-protein kinase pim-1	P11309	PIM1_HUMAN	Homo sapiens	3	0.7767
Lactoylglutathione lyase	Q9CPU0	LGUL_MOUSE	Mus musculus	2	0.7766
Prostaglandin reductase 2	Q8N8N7	PTGR2_HUMAN	Homo sapiens	3	0.7706
Proto-oncogene tyrosine-protein kinase Src	P00523	SRC_CHICK	Gallus gallus	3	0.7695
Mycocyclosin synthase	P9WPP7	CP121_MYCTU	Mycobacterium tuberculosis	3	0.7685
Lactoperoxidase	P80025	PERL_BOVIN	Bos taurus	3	0.7647
Protein ppBat	Q8A8A4	Q8A8A4_BACTN	Bacteroides thetaiotaomicron VPI-5482	2	0.7597
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.7574
Genome polyprotein	P26663	POLG_HCVBK	Hepatitis C virus genotype 1b	3	0.7572
Reductase homolog	Q9ZGC1	Q9ZGC1_STRCY	Streptomyces cyanogenus	4	0.7529
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.7503
Cell division cycle 7-related protein kinase	O00311	CDC7_HUMAN	Homo sapiens	3	0.7494
Dipeptidyl peptidase 4	P27487	DPP4_HUMAN	Homo sapiens	3	0.7468
Genome polyprotein	O92972	POLG_HCVJ4	Hepatitis C virus genotype 1b	3	0.7446
Angiopoietin-1 receptor	Q02763	TIE2_HUMAN	Homo sapiens	3	0.7426
Bromodomain adjacent to zinc finger domain protein 2B	Q9UIF8	BAZ2B_HUMAN	Homo sapiens	2	0.7417
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7362
Cyclin homolog	Q01043	CGH2_SHV21	Saimiriine herpesvirus 2	5	0.7360
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7309
Mitogen-activated protein kinase 1	P28482	MK01_HUMAN	Homo sapiens	3	0.7284
Transcriptional regulator, PadR-like family	A2RI36	A2RI36_LACLM	Lactococcus lactis subsp. cremoris	2	0.7259
4-hydroxyphenylacetate 3-monooxygenase	Q8YHT7	Q8YHT7_BRUME	Brucella melitensis biotype 1	2	0.7258
Dipeptidyl peptidase 4	P27487	DPP4_HUMAN	Homo sapiens	3	0.7239
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	4	0.7237
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	4	0.7237
Tyrosine-protein kinase Lck	P06239	LCK_HUMAN	Homo sapiens	3	0.7233
Polymerase acidic protein	C3W5S0	C3W5S0_I09A0	Influenza A virus	2	0.7219
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.7217
Liver carboxylesterase 1	P23141	EST1_HUMAN	Homo sapiens	2	0.7148
prolyl oligopeptidase	Q9X6R4	Q9X6R4_AERCA	Aeromonas caviae	3	0.7138
Lethal(3)malignant brain tumor-like protein 1	Q9Y468	LMBL1_HUMAN	Homo sapiens	3	0.7137
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.7137
Mycocyclosin synthase	P9WPP7	CP121_MYCTU	Mycobacterium tuberculosis	3	0.7131
cAMP-dependent protein kinase type I-alpha regulatory subunit	P00514	KAP0_BOVIN	Bos taurus	2	0.7131
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7125
cGMP-specific 3',5'-cyclic phosphodiesterase	O76074	PDE5A_HUMAN	Homo sapiens	3	0.7125
Acetylcholinesterase	P21836	ACES_MOUSE	Mus musculus	2	0.7121
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	2	0.7115
Cytosolic purine 5'-nucleotidase	P49902	5NTC_HUMAN	Homo sapiens	2	0.7082
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	2	0.7064
Corticosteroid-binding globulin	P08185	CBG_HUMAN	Homo sapiens	2	0.7057
Chymotrypsinogen A	P00766	CTRA_BOVIN	Bos taurus	3	0.7035
Neuropilin-1	O14786	NRP1_HUMAN	Homo sapiens	3	0.7024
N-terminal acetyltransferase A complex subunit NAT1	P12945	NAT1_YEAST	Saccharomyces cerevisiae	2	0.7008

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