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7,7'-dihydroxy-8,8'-biscoumarin

Family: Plantae - Guttiferae
Kingdom: Plantae
Class: Coumarin
- Subclass: Coumarin Derivative

Canonical Smiles	O=c1ccc2c(o1)c(c(cc2)O)c1c(O)ccc2c1oc(=O)cc2
InChI	InChI=1S/C18H10O6/c19-11-5-1-9-3-7-13(21)23-17(9)15(11)16-12(20)6-2-10-4-8-14(22)24-18(10)16/h1-8,19-20H
InChIKey	GSWJQORLOFYJTP-UHFFFAOYSA-N
Formula	C₁₈H₁₀O₆
HBA	6
HBD	2
MW	322.27
Rotatable Bonds	1
TPSA	100.88
LogP	2.98
Number Rings	4
Number Aromatic Rings	4
Heavy Atom Count	24
Formal Charge	0
Fraction CSP3	0.0
Exact Mass	322.05
Number of Lipinski Rule Violations	0

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Hypericum riparium	Guttiferae	Plantae	269018

Showing of synonyms

Tanemossu SA, Franke K, et al. (2014). Rare biscoumarin derivatives and flavonoids from Hypericum riparium.. Phytochemistry,2014, 105, 171-177. [View] [PubMed]

Pubchem: 14463055

Cas: 126221-42-9

No compound-protein relationship available.

SMILES: O=c(o1)ccc(c12)cccc2-c3cccc(c34)ccc(=O)o4

Level: 1

Mol. Weight: 322.27 g/mol

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

Level: 0

Mol. Weight: 322.27 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -4.9
Human Oral Bioavailability 20%: Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.620
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -1.1

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 1.310
Plasma Protein Binding: 89.78
Steady State Volume of Distribution: -

Metabolism

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

Excretion

Clearance: 1.160
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Safe
Bioconcentration Factor: 0.710
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Toxic
Eye Corrosion: Safe
Eye Irritation: Toxic
Maximum Tolerated Dose: 0.910
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 4.360
Micronucleos: Toxic
NR-AhR: Toxic
NR-AR: Safe
NR-AR-LBD: Safe
NR-Aromatase: Safe
NR-ER: Toxic
NR-ER-LBD: Safe
NR-GR: Toxic
NR-PPAR-gamma: Safe
NR-TR: Safe
T. Pyriformis: 2.600
Rat (Acute): 2.450
Rat (Chronic Oral): 2.180
Fathead Minnow: 4.920
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: 512.900
Hydration Free Energy: -11.460
Log(D) at pH=7.4: 1.910
Log(P): 2.06
Log S: -5.01
Log(Vapor Pressure): -10.38
Melting Point: 352.86
pKa Acid: 9.6
pKa Basic: 5.92

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Peptidyl-prolyl cis-trans isomerase FKBP1A	P62942	FKB1A_HUMAN	Homo sapiens	3	0.9140
Abscisic acid receptor PYL2	O80992	PYL2_ARATH	Arabidopsis thaliana	3	0.8869
Abscisic acid receptor PYL2	O80992	PYL2_ARATH	Arabidopsis thaliana	3	0.8544
Angiotensin-converting enzyme 2	Q9BYF1	ACE2_HUMAN	Homo sapiens	3	0.8536
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	3	0.8392
Mitogen-activated protein kinase 14	Q16539	MK14_HUMAN	Homo sapiens	3	0.8354
Gag-Pol polyprotein	P03369	POL_HV1A2	Human immunodeficiency virus type 1 group M subtype B	3	0.8265
Biphenyl dioxygenase subunit alpha	P37333	BPHA_PARXL	Paraburkholderia xenovorans	3	0.8262
M17 leucyl aminopeptidase	Q8IL11	Q8IL11_PLAF7	Plasmodium falciparum	3	0.8245
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	3	0.8234
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.8011
Glutamate receptor ionotropic, kainate 1	P22756	GRIK1_RAT	Rattus norvegicus	3	0.7899
Gentisate 1,2-dioxygenase	Q67FT0	Q67FT0_PSESE	Pseudaminobacter salicylatoxidans	3	0.7892
11-beta-hydroxysteroid dehydrogenase 1	Q6QLL4	DHI1_CAVPO	Cavia porcellus	3	0.7872
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	3	0.7834
Riboflavin synthase	P0AFU8	RISA_ECOLI	Escherichia coli	3	0.7825
Alpha-1-acid glycoprotein 2	P19652	A1AG2_HUMAN	Homo sapiens	3	0.7783
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.7758
1-deoxy-D-xylulose 5-phosphate reductoisomerase	P9WNS1	DXR_MYCTU	Mycobacterium tuberculosis	3	0.7733
HTH-type transcriptional regulator QacR	P0A0N4	QACR_STAAU	Staphylococcus aureus	3	0.7731
Norsolorinic acid synthase	Q12053	AFLC_ASPPU	Aspergillus parasiticus	3	0.7688
Gag-Pol polyprotein	P04584	POL_HV2RO	Human immunodeficiency virus type 2 subtype A	4	0.7664
Abscisic acid receptor PYR1	O49686	PYR1_ARATH	Arabidopsis thaliana	3	0.7649
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform	P48736	PK3CG_HUMAN	Homo sapiens	3	0.7606
Serpin domain-containing protein	H0ZQY2	H0ZQY2_TAEGU	Taeniopygia guttata	3	0.7591
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7548
Type IV / VI secretion system DotU domain-containing protein	Q9KN50	Q9KN50_VIBCH	Vibrio cholerae serotype O1	2	0.7546
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7479
Polymerase acidic protein	C3W5S0	C3W5S0_I09A0	Influenza A virus	2	0.7452
Serine/threonine-protein kinase PLK2	Q9NYY3	PLK2_HUMAN	Homo sapiens	3	0.7448
Adenylate cyclase type 5	P30803	ADCY5_CANLF	Canis lupus familiaris	4	0.7431
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7428
Mitochondrial poly(A) polymerase	F1NBW0	F1NBW0_CHICK	Gallus gallus	2	0.7427
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	2	0.7425
Pheromone-binding protein ASP1	Q9U9J6	Q9U9J6_APIME	Apis mellifera	3	0.7399
Methionine aminopeptidase	P0AE18	MAP1_ECOLI	Escherichia coli	3	0.7389
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7368
Beta-secretase 2	Q9Y5Z0	BACE2_HUMAN	Homo sapiens	2	0.7339
Gag-Pol polyprotein	P04584	POL_HV2RO	Human immunodeficiency virus type 2 subtype A	4	0.7328
Metallo-beta-lactamase type 2	C7C422	BLAN1_KLEPN	Klebsiella pneumoniae	2	0.7322
Glutamate receptor ionotropic, kainate 1	P22756	GRIK1_RAT	Rattus norvegicus	2	0.7308
Adenylate cyclase type 5	P30803	ADCY5_CANLF	Canis lupus familiaris	3	0.7305
Stromelysin-1	P08254	MMP3_HUMAN	Homo sapiens	3	0.7258
Polymerase acidic protein	C3W5S0	C3W5S0_I09A0	Influenza A virus	2	0.7232
Adenylate cyclase type 5	P30803	ADCY5_CANLF	Canis lupus familiaris	3	0.7199
Mandelate racemase	P11444	MANR_PSEPU	Pseudomonas putida	3	0.7158
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7156
Benzoylformate decarboxylase	P20906	MDLC_PSEPU	Pseudomonas putida	3	0.7154
Serine/threonine-protein kinase PLK2	Q9NYY3	PLK2_HUMAN	Homo sapiens	3	0.7149
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	2	0.7132
Cytohesin-2	Q99418	CYH2_HUMAN	Homo sapiens	3	0.7130
Dipeptidyl peptidase 4	P27487	DPP4_HUMAN	Homo sapiens	3	0.7111
Activin receptor type-1	Q04771	ACVR1_HUMAN	Homo sapiens	3	0.7108
Pheromone-binding protein ASP1	Q9U9J6	Q9U9J6_APIME	Apis mellifera	3	0.7107
Mycinamicin III 3''-O-methyltransferase	Q49492	MYCF_MICGR	Micromonospora griseorubida	2	0.7104
Cytochrome P450 2C19	P33261	CP2CJ_HUMAN	Homo sapiens	3	0.7100
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7078
Thymidylate synthase	P00469	TYSY_LACCA	Lacticaseibacillus casei	2	0.7077
CCA-adding enzyme	O28126	CCA_ARCFU	Archaeoglobus fulgidus	2	0.7075
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	3	0.7073
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.7072
4-hydroxyphenylacetate 3-monooxygenase, reductase component	Q5SJP7	HPAC_THET8	Thermus thermophilus	3	0.7070
N-terminal acetyltransferase A complex subunit NAT1	P12945	NAT1_YEAST	Saccharomyces cerevisiae	2	0.7070
Cytosol aminopeptidase	P00727	AMPL_BOVIN	Bos taurus	2	0.7065
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.7052
Streptogramin A acetyltransferase	P50870	VATD_ENTFC	Enterococcus faecium	3	0.7037
Gag-Pol polyprotein	P05896	POL_SIVM1	Simian immunodeficiency virus	3	0.7035
Carbonic anhydrase 4	Q64444	CAH4_MOUSE	Mus musculus	2	0.7023
cGMP-specific 3',5'-cyclic phosphodiesterase	O76074	PDE5A_HUMAN	Homo sapiens	4	0.7015
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7007
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.7004

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