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Cleomiscosin C

Family: Plantae - Euphorbiaceae
Kingdom: Plantae
Class: Coumarin

Canonical Smiles	OC[C@H]1Oc2c(O[C@@H]1c1cc(OC)c(c(c1)OC)O)c(OC)cc1c2oc(=O)cc1
InChI	InChI=1S/C21H20O9/c1-25-12-7-11(8-13(26-2)17(12)24)18-15(9-22)28-21-19-10(4-5-16(23)29-19)6-14(27-3)20(21)30-18/h4-8,15,18,22,24H,9H2,1-3H3/t15-,18-/m1/s1
InChIKey	GZXPCBAETDEQAX-CRAIPNDOSA-N
Formula	C₂₁H₂₀O₉
HBA	9
HBD	2
MW	416.38
Rotatable Bonds	5
TPSA	116.82
LogP	2.4
Number Rings	4
Number Aromatic Rings	3
Heavy Atom Count	30
Formal Charge	0
Fraction CSP3	0.29
Exact Mass	416.11
Number of Lipinski Rule Violations	0

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Euphorbia bupleuroides	Euphorbiaceae	Plantae	1532838

Showing of synonyms

Aichour S, Haba H, et al. (2014). Terpenoids and other constituents from Euphorbia bupleuroides. Phytochemistry,2014,10,198-203. [View]

Pubchem: 11464176

Cas: 84575-10-0

Zinc: ZINC000013400299

Nmrshiftdb2: 60027356

Chembl: CHEMBL465491

No compound-protein relationship available.

SMILES: O=c(o1)ccc2ccc(c3c12)OC(CO3)c4ccccc4

Level: 1

Mol. Weight: 416.38 g/mol

SMILES: O1CCOc(c1c23)ccc2ccc(=O)o3

Level: 0

Mol. Weight: 416.38 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 416.38 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -4.88
Human Oral Bioavailability 20%: Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.770
Human Oral Bioavailability 50%: Bioavailable
P-Glycoprotein Inhibitor: Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -1.93

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 1.440
Plasma Protein Binding: 84.19
Steady State Volume of Distribution: -

Metabolism

Breast Cancer Resistance Protein: Inhibitor
CYP 1A2 Inhibitor: Non-Inhibitor
CYP 1A2 Substrate: Non-Substrate
CYP 2C19 Inhibitor: Inhibitor
CYP 2C19 Substrate: Non-Substrate
CYP 2C9 Inhibitor: Non-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: 8.210
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: 1.610
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 1.210
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 6.330
Micronucleos: Toxic
NR-AhR: Toxic
NR-AR: Safe
NR-AR-LBD: Safe
NR-Aromatase: Safe
NR-ER: Safe
NR-ER-LBD: Safe
NR-GR: Safe
NR-PPAR-gamma: Safe
NR-TR: Safe
T. Pyriformis: -35.670
Rat (Acute): 2.150
Rat (Chronic Oral): 2.240
Fathead Minnow: 4.730
Respiratory Disease: Toxic
Skin Sensitisation: Safe
SR-ARE: Toxic
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Safe
SR-p53: Toxic

General Properties

Boiling Point: 488.830
Hydration Free Energy: -4.870
Log(D) at pH=7.4: 1.980
Log(P): 1.12
Log S: -3.99
Log(Vapor Pressure): -8.6
Melting Point: 196.15
pKa Acid: 7.28
pKa Basic: 0.05

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Ribosomal small subunit pseudouridine synthase A	P0AA43	RSUA_ECOLI	Escherichia coli	3	0.9184
Ribosomal small subunit pseudouridine synthase A	P0AA43	RSUA_ECOLI	Escherichia coli	3	0.9184
Serine/threonine-protein kinase 24	Q9Y6E0	STK24_HUMAN	Homo sapiens	3	0.8999
Serine/threonine-protein kinase 24	Q9Y6E0	STK24_HUMAN	Homo sapiens	3	0.8999
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.8969
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.8969
WxcM-like protein	Q12KT8	Q12KT8_SHEDO	Shewanella denitrificans	4	0.8967
WxcM-like protein	Q12KT8	Q12KT8_SHEDO	Shewanella denitrificans	4	0.8967
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.8850
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.8850
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8694
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8694
Mycocyclosin synthase	P9WPP7	CP121_MYCTU	Mycobacterium tuberculosis	3	0.8671
Mycocyclosin synthase	P9WPP7	CP121_MYCTU	Mycobacterium tuberculosis	3	0.8671
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8608
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8608
Thymidine phosphorylase	Q7CP66	TYPH_SALTY	Salmonella typhimurium	3	0.8495
Thymidine phosphorylase	Q7CP66	TYPH_SALTY	Salmonella typhimurium	3	0.8495
Serine/threonine-protein kinase 10	O94804	STK10_HUMAN	Homo sapiens	3	0.8458
Serine/threonine-protein kinase 10	O94804	STK10_HUMAN	Homo sapiens	3	0.8458
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.8387
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.8387
Mycocyclosin synthase	P9WPP7	CP121_MYCTU	Mycobacterium tuberculosis	4	0.8348
Mycocyclosin synthase	P9WPP7	CP121_MYCTU	Mycobacterium tuberculosis	4	0.8348
Bromodomain-containing protein 2	P25440	BRD2_HUMAN	Homo sapiens	3	0.8341
Bromodomain-containing protein 2	P25440	BRD2_HUMAN	Homo sapiens	3	0.8341
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.8247
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.8247
D-aminoacyl-tRNA deacylase	Q8IIS0	DTD_PLAF7	Plasmodium falciparum	3	0.8246
D-aminoacyl-tRNA deacylase	Q8IIS0	DTD_PLAF7	Plasmodium falciparum	3	0.8246
HTH-type transcriptional regulator TtgR	Q9AIU0	TTGR_PSEPT	Pseudomonas putida	3	0.8225
HTH-type transcriptional regulator TtgR	Q9AIU0	TTGR_PSEPT	Pseudomonas putida	3	0.8225
Carminomycin 4-O-methyltransferase DnrK	Q06528	DNRK_STRPE	Streptomyces peucetius	3	0.8174
Carminomycin 4-O-methyltransferase DnrK	Q06528	DNRK_STRPE	Streptomyces peucetius	3	0.8174
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	3	0.8130
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	3	0.8130
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.8123
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.8123
Peroxisome proliferator-activated receptor gamma	P37231	PPARG_HUMAN	Homo sapiens	3	0.8056
Peroxisome proliferator-activated receptor gamma	P37231	PPARG_HUMAN	Homo sapiens	3	0.8056
NADH:flavin oxidoreductase Sye1	Q8EEC8	Q8EEC8_SHEON	Shewanella oneidensis	3	0.7922
NADH:flavin oxidoreductase Sye1	Q8EEC8	Q8EEC8_SHEON	Shewanella oneidensis	3	0.7922
Rhodopsin kinase GRK1	P28327	GRK1_BOVIN	Bos taurus	3	0.7825
Rhodopsin kinase GRK1	P28327	GRK1_BOVIN	Bos taurus	3	0.7825
Tau-tubulin kinase 1	Q5TCY1	TTBK1_HUMAN	Homo sapiens	3	0.7816
Tau-tubulin kinase 1	Q5TCY1	TTBK1_HUMAN	Homo sapiens	3	0.7816
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7805
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7805
Hypoxanthine phosphoribosyltransferase	Q4DRC4	Q4DRC4_TRYCC	Trypanosoma cruzi	3	0.7760
Hypoxanthine phosphoribosyltransferase	Q4DRC4	Q4DRC4_TRYCC	Trypanosoma cruzi	3	0.7760
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7736
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7736
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7717
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7717
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	5	0.7706
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	5	0.7706
Thymidylate synthase	P0A884	TYSY_ECOLI	Escherichia coli	4	0.7653
Thymidylate synthase	P0A884	TYSY_ECOLI	Escherichia coli	4	0.7653
Genome polyprotein	P26663	POLG_HCVBK	Hepatitis C virus genotype 1b	3	0.7616
Genome polyprotein	P26663	POLG_HCVBK	Hepatitis C virus genotype 1b	3	0.7616
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	3	0.7566
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	3	0.7566
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform	P48736	PK3CG_HUMAN	Homo sapiens	3	0.7554
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform	P48736	PK3CG_HUMAN	Homo sapiens	3	0.7554
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	4	0.7551
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	4	0.7551
Flavoredoxin	Q72HI0	Q72HI0_THET2	Thermus thermophilus	3	0.7509
Flavoredoxin	Q72HI0	Q72HI0_THET2	Thermus thermophilus	3	0.7509
Thymidylate synthase	P0A886	TYSY_ECO57	Escherichia coli O157:H7	3	0.7506
Thymidylate synthase	P0A886	TYSY_ECO57	Escherichia coli O157:H7	3	0.7506
Cyclin-dependent kinase 9	P50750	CDK9_HUMAN	Homo sapiens	3	0.7502
Cyclin-dependent kinase 9	P50750	CDK9_HUMAN	Homo sapiens	3	0.7502
GTPase KRas	P01116	RASK_HUMAN	Homo sapiens	3	0.7465
GTPase KRas	P01116	RASK_HUMAN	Homo sapiens	3	0.7465
Purine nucleoside phosphorylase	P00491	PNPH_HUMAN	Homo sapiens	3	0.7428
Purine nucleoside phosphorylase	P00491	PNPH_HUMAN	Homo sapiens	3	0.7428
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7378
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7378
Cytochrome P450 2C8	P10632	CP2C8_HUMAN	Homo sapiens	3	0.7377
Cytochrome P450 2C8	P10632	CP2C8_HUMAN	Homo sapiens	3	0.7377
Glycogen synthase	Q9V2J8	Q9V2J8_PYRAB	Pyrococcus abyssi	3	0.7369
Glycogen synthase	Q9V2J8	Q9V2J8_PYRAB	Pyrococcus abyssi	3	0.7369
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	4	0.7363
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	4	0.7363
[LysW]-aminoadipate kinase	O50147	LYSZ_THET2	Thermus thermophilus	3	0.7357
[LysW]-aminoadipate kinase	O50147	LYSZ_THET2	Thermus thermophilus	3	0.7357
Homoserine dehydrogenase	P31116	DHOM_YEAST	Saccharomyces cerevisiae	3	0.7357
Homoserine dehydrogenase	P31116	DHOM_YEAST	Saccharomyces cerevisiae	3	0.7357
Caspase-6	P55212	CASP6_HUMAN	Homo sapiens	3	0.7351
Caspase-6	P55212	CASP6_HUMAN	Homo sapiens	3	0.7351
Pentaerythritol tetranitrate reductase	P71278	P71278_ENTCL	Enterobacter cloacae	2	0.7311
Pentaerythritol tetranitrate reductase	P71278	P71278_ENTCL	Enterobacter cloacae	2	0.7311
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7290
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7290
Histone deacetylase 4	P56524	HDAC4_HUMAN	Homo sapiens	3	0.7263
Histone deacetylase 4	P56524	HDAC4_HUMAN	Homo sapiens	3	0.7263
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7255
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7255
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	3	0.7231
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	3	0.7231
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	3	0.7219
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	3	0.7219
Flavin-dependent monooxygenase	Q93L51	TETX_BACT4	Bacteroides thetaiotaomicron	3	0.7203
Flavin-dependent monooxygenase	Q93L51	TETX_BACT4	Bacteroides thetaiotaomicron	3	0.7203
AcsD	Q93AT8	Q93AT8_DICCH	Dickeya chrysanthemi	3	0.7174
AcsD	Q93AT8	Q93AT8_DICCH	Dickeya chrysanthemi	3	0.7174
Uracil-DNA glycosylase	P13051	UNG_HUMAN	Homo sapiens	4	0.7162
Uracil-DNA glycosylase	P13051	UNG_HUMAN	Homo sapiens	4	0.7162
Thymidine kinase	P0DTH5	KITH_HHV11	Human herpesvirus 1	3	0.7141
Thymidine kinase	P0DTH5	KITH_HHV11	Human herpesvirus 1	3	0.7141
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7129
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7129
Riboflavin synthase	P0AFU8	RISA_ECOLI	Escherichia coli	4	0.7127
Riboflavin synthase	P0AFU8	RISA_ECOLI	Escherichia coli	4	0.7127
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7126
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7126
Nitric oxide synthase oxygenase	O34453	NOSO_BACSU	Bacillus subtilis	3	0.7118
Nitric oxide synthase oxygenase	O34453	NOSO_BACSU	Bacillus subtilis	3	0.7118
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7112
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7112
Gag-Pol polyprotein	P03367	POL_HV1BR	Human immunodeficiency virus type 1 group M subtype B	3	0.7108
Gag-Pol polyprotein	P03367	POL_HV1BR	Human immunodeficiency virus type 1 group M subtype B	3	0.7108
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7058
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7058
Hypoxanthine-guanine phosphoribosyltransferase	P00492	HPRT_HUMAN	Homo sapiens	3	0.7045
Hypoxanthine-guanine phosphoribosyltransferase	P00492	HPRT_HUMAN	Homo sapiens	3	0.7045
Bifunctional protein GAL10	P04397	GAL10_YEAST	Saccharomyces cerevisiae	4	0.7026
Bifunctional protein GAL10	P04397	GAL10_YEAST	Saccharomyces cerevisiae	4	0.7026
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.7015
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.7015
Hypoxanthine-guanine phosphoribosyltransferase	P00492	HPRT_HUMAN	Homo sapiens	3	0.7003
Hypoxanthine-guanine phosphoribosyltransferase	P00492	HPRT_HUMAN	Homo sapiens	3	0.7003

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