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Hainanmurpanin

Family: Rutaceae
Kingdom: Plantae
Class: Coumarin

Canonical Smiles	COc1ccc2c(c1C(C(=O)C(C)C)OC(=O)C)oc(=O)cc2
InChI	InChI=1S/C17H18O6/c1-9(2)15(20)17(22-10(3)18)14-12(21-4)7-5-11-6-8-13(19)23-16(11)14/h5-9,17H,1-4H3
InChIKey	VLHOVPZUSXEINR-UHFFFAOYSA-N
Formula	C₁₇H₁₈O₆
HBA	6
HBD	0
MW	318.33
Rotatable Bonds	5
TPSA	82.81
LogP	2.63
Number Rings	2
Number Aromatic Rings	2
Heavy Atom Count	23
Formal Charge	0
Fraction CSP3	0.35
Exact Mass	318.11
Number of Lipinski Rule Violations	0

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Murraya exotica	Rutaceae	Plantae	2901850

Showing of synonyms

Negi N, Ochi A, et al. (2005). Two new dimeric coumarins isolated from Murraya exotica. Chemical and Pharmaceutical Bulletin,2005,53(9),1180-1182. [View] [PubMed]

Pubchem: 5317952

Cas: 95360-22-8

Gnps: CCMSLIB00004685029

Chebi: 181255

Nmrshiftdb2: 60062029

No compound-protein relationship available.

SMILES: c1cccc(c12)oc(=O)cc2

Level: 0

Mol. Weight: 146.15 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -4.5
Human Oral Bioavailability 20%: Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.550
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -2.35

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Penetrable
Fraction Unbound (Human): 0.760
Plasma Protein Binding: 41.07
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: Non-Substrate
CYP 2C9 Inhibitor: Inhibitor
CYP 2C9 Substrate: Non-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: 4.550
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Toxic
Avian: Safe
Bee: Safe
Bioconcentration Factor: 1.210
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 1.420
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 5.740
Micronucleos: Safe
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: 3.080
Rat (Acute): 2.770
Rat (Chronic Oral): 2.130
Fathead Minnow: 4.670
Respiratory Disease: Safe
Skin Sensitisation: Safe
SR-ARE: Safe
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Safe
SR-p53: Safe

General Properties

Boiling Point: 398.380
Hydration Free Energy: -9.140
Log(D) at pH=7.4: 1.650
Log(P): 2.1
Log S: -4.1
Log(Vapor Pressure): -6.18
Melting Point: 122.16
pKa Acid: 6.86
pKa Basic: 4.23

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
NAD-capped RNA hydrolase NudC	P32664	NUDC_ECOLI	Escherichia coli	3	0.9134
NAD-capped RNA hydrolase NudC	P32664	NUDC_ECOLI	Escherichia coli	3	0.9134
NADH:flavin oxidoreductase Sye1	Q8EEC8	Q8EEC8_SHEON	Shewanella oneidensis	3	0.8973
NADH:flavin oxidoreductase Sye1	Q8EEC8	Q8EEC8_SHEON	Shewanella oneidensis	3	0.8973
Bromodomain-containing protein 2	P25440	BRD2_HUMAN	Homo sapiens	3	0.8965
Bromodomain-containing protein 2	P25440	BRD2_HUMAN	Homo sapiens	3	0.8965
cGMP-dependent protein kinase 2	Q13237	KGP2_HUMAN	Homo sapiens	3	0.8877
cGMP-dependent protein kinase 2	Q13237	KGP2_HUMAN	Homo sapiens	3	0.8877
Beta-2 adrenergic receptor	P07550	ADRB2_HUMAN	Homo sapiens	3	0.8667
Beta-2 adrenergic receptor	P07550	ADRB2_HUMAN	Homo sapiens	3	0.8667
cAMP-dependent protein kinase type I-alpha regulatory subunit	P00514	KAP0_BOVIN	Bos taurus	3	0.8646
cAMP-dependent protein kinase type I-alpha regulatory subunit	P00514	KAP0_BOVIN	Bos taurus	3	0.8646
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	3	0.8632
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	3	0.8632
cAMP-dependent protein kinase type II-beta regulatory subunit	P12369	KAP3_RAT	Rattus norvegicus	3	0.8578
cAMP-dependent protein kinase type II-beta regulatory subunit	P12369	KAP3_RAT	Rattus norvegicus	3	0.8578
Carminomycin 4-O-methyltransferase DnrK	Q06528	DNRK_STRPE	Streptomyces peucetius	3	0.8528
Carminomycin 4-O-methyltransferase DnrK	Q06528	DNRK_STRPE	Streptomyces peucetius	3	0.8528
cGMP-dependent protein kinase 1	Q13976	KGP1_HUMAN	Homo sapiens	3	0.8495
cGMP-dependent protein kinase 1	Q13976	KGP1_HUMAN	Homo sapiens	3	0.8495
cAMP-dependent protein kinase type I-alpha regulatory subunit	P00514	KAP0_BOVIN	Bos taurus	3	0.8271
cAMP-dependent protein kinase type I-alpha regulatory subunit	P00514	KAP0_BOVIN	Bos taurus	3	0.8271
Mycocyclosin synthase	P9WPP7	CP121_MYCTU	Mycobacterium tuberculosis	2	0.8248
Mycocyclosin synthase	P9WPP7	CP121_MYCTU	Mycobacterium tuberculosis	2	0.8248
Bromodomain-containing protein 2	P25440	BRD2_HUMAN	Homo sapiens	3	0.8206
Bromodomain-containing protein 2	P25440	BRD2_HUMAN	Homo sapiens	3	0.8206
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform	P48736	PK3CG_HUMAN	Homo sapiens	3	0.8201
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform	P48736	PK3CG_HUMAN	Homo sapiens	3	0.8201
Acetylcholinesterase	P21836	ACES_MOUSE	Mus musculus	2	0.8014
Acetylcholinesterase	P21836	ACES_MOUSE	Mus musculus	2	0.8014
Thymidylate synthase	P00469	TYSY_LACCA	Lacticaseibacillus casei	3	0.7975
Thymidylate synthase	P00469	TYSY_LACCA	Lacticaseibacillus casei	3	0.7975
Glucose-1-phosphate thymidylyltransferase	Q9AGY4	Q9AGY4_ANETH	Aneurinibacillus thermoaerophilus	3	0.7898
Glucose-1-phosphate thymidylyltransferase	Q9AGY4	Q9AGY4_ANETH	Aneurinibacillus thermoaerophilus	3	0.7898
Orotidine 5'-phosphate decarboxylase	Q5L0U0	PYRF_GEOKA	Geobacillus kaustophilus	3	0.7771
Orotidine 5'-phosphate decarboxylase	Q5L0U0	PYRF_GEOKA	Geobacillus kaustophilus	3	0.7771
Beta-2 adrenergic receptor	P07550	ADRB2_HUMAN	Homo sapiens	3	0.7744
Beta-2 adrenergic receptor	P07550	ADRB2_HUMAN	Homo sapiens	3	0.7744
Methionine aminopeptidase	P0AE18	MAP1_ECOLI	Escherichia coli	3	0.7736
Methionine aminopeptidase	P0AE18	MAP1_ECOLI	Escherichia coli	3	0.7736
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7732
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7732
Biflaviolin synthase CYP158A1	Q9KZF5	C1581_STRCO	Streptomyces coelicolor / M145)	3	0.7696
Biflaviolin synthase CYP158A1	Q9KZF5	C1581_STRCO	Streptomyces coelicolor / M145)	3	0.7696
ActVA 6 protein	Q53908	Q53908_STRCH	Streptomyces coelicolor	3	0.7660
ActVA 6 protein	Q53908	Q53908_STRCH	Streptomyces coelicolor	3	0.7660
4-hydroxyphenylacetate 3-monooxygenase, reductase component	Q5SJP7	HPAC_THET8	Thermus thermophilus	3	0.7631
4-hydroxyphenylacetate 3-monooxygenase, reductase component	Q5SJP7	HPAC_THET8	Thermus thermophilus	3	0.7631
Nuclear receptor subfamily 1 group I member 2	O75469	NR1I2_HUMAN	Homo sapiens	3	0.7609
Nuclear receptor subfamily 1 group I member 2	O75469	NR1I2_HUMAN	Homo sapiens	3	0.7609
Peptidyl-prolyl cis-trans isomerase FKBP5	Q13451	FKBP5_HUMAN	Homo sapiens	3	0.7602
Peptidyl-prolyl cis-trans isomerase FKBP5	Q13451	FKBP5_HUMAN	Homo sapiens	3	0.7602
Bifunctional dihydrofolate reductase-thymidylate synthase	P13922	DRTS_PLAFK	Plasmodium falciparum	2	0.7567
Bifunctional dihydrofolate reductase-thymidylate synthase	P13922	DRTS_PLAFK	Plasmodium falciparum	2	0.7567
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7557
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7557
Biflaviolin synthase CYP158A2	Q9FCA6	C1582_STRCO	Streptomyces coelicolor / M145)	3	0.7487
Biflaviolin synthase CYP158A2	Q9FCA6	C1582_STRCO	Streptomyces coelicolor / M145)	3	0.7487
Biflaviolin synthase CYP158A2	Q9FCA6	C1582_STRCO	Streptomyces coelicolor / M145)	3	0.7474
Biflaviolin synthase CYP158A2	Q9FCA6	C1582_STRCO	Streptomyces coelicolor / M145)	3	0.7474
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7450
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7450
Acetylcholinesterase	P04058	ACES_TETCF	Tetronarce californica	3	0.7430
Acetylcholinesterase	P04058	ACES_TETCF	Tetronarce californica	3	0.7430
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	2	0.7429
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	2	0.7429
cAMP-dependent protein kinase type I-alpha regulatory subunit	P00514	KAP0_BOVIN	Bos taurus	3	0.7424
cAMP-dependent protein kinase type I-alpha regulatory subunit	P00514	KAP0_BOVIN	Bos taurus	3	0.7424
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	3	0.7406
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	3	0.7406
Casein kinase II subunit alpha'	P19784	CSK22_HUMAN	Homo sapiens	3	0.7387
Casein kinase II subunit alpha'	P19784	CSK22_HUMAN	Homo sapiens	3	0.7387
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7385
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7385
Adenylate cyclase type 5	P30803	ADCY5_CANLF	Canis lupus familiaris	3	0.7373
Adenylate cyclase type 5	P30803	ADCY5_CANLF	Canis lupus familiaris	3	0.7373
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1	P04191	AT2A1_RABIT	Oryctolagus cuniculus	2	0.7371
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1	P04191	AT2A1_RABIT	Oryctolagus cuniculus	2	0.7371
Genome polyprotein	Q2YHF0	POLG_DEN4T	Dengue virus type 4	3	0.7352
Genome polyprotein	Q2YHF0	POLG_DEN4T	Dengue virus type 4	3	0.7352
Chitinase	Q54276	Q54276_SERMA	Serratia marcescens	2	0.7315
Chitinase	Q54276	Q54276_SERMA	Serratia marcescens	2	0.7315
Metallo-beta-lactamase type 2	C7C422	BLAN1_KLEPN	Klebsiella pneumoniae	2	0.7286
Metallo-beta-lactamase type 2	C7C422	BLAN1_KLEPN	Klebsiella pneumoniae	2	0.7286
LIM domain kinase 1	P53667	LIMK1_HUMAN	Homo sapiens	2	0.7281
LIM domain kinase 1	P53667	LIMK1_HUMAN	Homo sapiens	2	0.7281
cAMP-dependent protein kinase catalytic subunit alpha	P17612	KAPCA_HUMAN	Homo sapiens	2	0.7277
cAMP-dependent protein kinase catalytic subunit alpha	P17612	KAPCA_HUMAN	Homo sapiens	2	0.7277
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	2	0.7259
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	2	0.7259
Adenylate cyclase type 5	P30803	ADCY5_CANLF	Canis lupus familiaris	3	0.7246
Adenylate cyclase type 5	P30803	ADCY5_CANLF	Canis lupus familiaris	3	0.7246
cAMP-dependent protein kinase catalytic subunit alpha	P00517	KAPCA_BOVIN	Bos taurus	2	0.7220
cAMP-dependent protein kinase catalytic subunit alpha	P00517	KAPCA_BOVIN	Bos taurus	2	0.7220
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1	P04191	AT2A1_RABIT	Oryctolagus cuniculus	2	0.7212
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1	P04191	AT2A1_RABIT	Oryctolagus cuniculus	2	0.7212
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	3	0.7209
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	3	0.7209
Pteridine reductase	O76290	O76290_TRYBB	Trypanosoma brucei brucei	2	0.7207
Pteridine reductase	O76290	O76290_TRYBB	Trypanosoma brucei brucei	2	0.7207
Mitochondrial poly(A) polymerase	F1NBW0	F1NBW0_CHICK	Gallus gallus	2	0.7197
Mitochondrial poly(A) polymerase	F1NBW0	F1NBW0_CHICK	Gallus gallus	2	0.7197
Albumin	P02768	ALBU_HUMAN	Homo sapiens	3	0.7190
Albumin	P02768	ALBU_HUMAN	Homo sapiens	3	0.7190
Polymerase acidic protein	C3W5S0	C3W5S0_I09A0	Influenza A virus	2	0.7188
Polymerase acidic protein	C3W5S0	C3W5S0_I09A0	Influenza A virus	2	0.7188
Type IV / VI secretion system DotU domain-containing protein	Q9KN50	Q9KN50_VIBCH	Vibrio cholerae serotype O1	2	0.7180
Type IV / VI secretion system DotU domain-containing protein	Q9KN50	Q9KN50_VIBCH	Vibrio cholerae serotype O1	2	0.7180
Aromatic-amino-acid aminotransferase	P95468	TYRB_PARDE	Paracoccus denitrificans	2	0.7145
Aromatic-amino-acid aminotransferase	P95468	TYRB_PARDE	Paracoccus denitrificans	2	0.7145
AcsD	Q93AT8	Q93AT8_DICCH	Dickeya chrysanthemi	3	0.7143
AcsD	Q93AT8	Q93AT8_DICCH	Dickeya chrysanthemi	3	0.7143
Uridine phosphorylase	P0A1F6	UDP_SALTY	Salmonella typhimurium	3	0.7115
Uridine phosphorylase	P0A1F6	UDP_SALTY	Salmonella typhimurium	3	0.7115
Adenosine kinase	Q9TVW2	ADK_TOXGO	Toxoplasma gondii	3	0.7114
Adenosine kinase	Q9TVW2	ADK_TOXGO	Toxoplasma gondii	3	0.7114
Sepiapterin reductase	Q64105	SPRE_MOUSE	Mus musculus	3	0.7107
Sepiapterin reductase	Q64105	SPRE_MOUSE	Mus musculus	3	0.7107
Catabolite activator protein	C3SQJ7	C3SQJ7_ECOLX	Escherichia coli	3	0.7087
Catabolite activator protein	C3SQJ7	C3SQJ7_ECOLX	Escherichia coli	3	0.7087
Bifunctional dihydrofolate reductase-thymidylate synthase	Q27783	DRTS_TRYBB	Trypanosoma brucei brucei	3	0.7066
Bifunctional dihydrofolate reductase-thymidylate synthase	Q27783	DRTS_TRYBB	Trypanosoma brucei brucei	3	0.7066
Lethal(3)malignant brain tumor-like protein 1	Q9Y468	LMBL1_HUMAN	Homo sapiens	3	0.7066
Lethal(3)malignant brain tumor-like protein 1	Q9Y468	LMBL1_HUMAN	Homo sapiens	3	0.7066
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	3	0.7060
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	3	0.7060
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial	Q0QF01	SDHA_PIG	Sus scrofa	3	0.7024
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial	Q0QF01	SDHA_PIG	Sus scrofa	3	0.7024
Histone deacetylase 8	Q9BY41	HDAC8_HUMAN	Homo sapiens	2	0.7016
Histone deacetylase 8	Q9BY41	HDAC8_HUMAN	Homo sapiens	2	0.7016

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