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(3R,4S)-4-hydroxymellein

Family: Fungi - Botryosphaeriaceae
Kingdom: Fungi
Class: Coumarin
- Subclass: Isocoumarin

Canonical Smiles	C[C@H]1OC(=O)c2c([C@@H]1O)cccc2O
InChI	InChI=1S/C10H10O4/c1-5-9(12)6-3-2-4-7(11)8(6)10(13)14-5/h2-5,9,11-12H,1H3/t5-,9-/m1/s1
InChIKey	STSOHAOGZMLWFR-MLUIRONXSA-N
Formula	C₁₀H₁₀O₄
HBA	4
HBD	2
MW	194.19
Rotatable Bonds	0
TPSA	66.76
LogP	0.98
Number Rings	2
Number Aromatic Rings	1
Heavy Atom Count	14
Formal Charge	0
Fraction CSP3	0.3
Exact Mass	194.06
Number of Lipinski Rule Violations	0

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Diplodia sapinea	Botryosphaeriaceae	Fungi	—

Showing of synonyms

Masi M, Di Lecce R, et al. (2021). Pinofuranoxins A and B, bioactive trisubstituted furanones produced by the invasive pathogen Diplodia sapinea. Journal of natural products, 2021, 84(9), 2600-2605. [View] [PubMed]

Pubchem: 10262028

Cas: 70287-70-6

Nmrshiftdb2: 20213235

Chembl: CHEMBL499001

Comptox: DTXSID60437474

No compound-protein relationship available.

SMILES: c1cccc(c12)CCOC2=O

Level: 0

Mol. Weight: 194.19 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -4.83
Human Oral Bioavailability 20%: Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.61
Human Oral Bioavailability 50%: Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -2.68

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Penetrable
Fraction Unbound (Human): 0.57
Plasma Protein Binding: 43.37
Steady State Volume of Distribution: -

Metabolism

Breast Cancer Resistance Protein: Non-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: 6.14
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Safe
Bioconcentration Factor: 0.2
Biodegradation: Toxic
Carcinogenesis: Safe
Crustacean: Safe
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Toxic
Maximum Tolerated Dose: -0.35
Liver Injury II: Safe
hERG Blockers: Safe
Daphnia Maga: 4.15
Micronucleos: Toxic
NR-AhR: Safe
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: 1.23
Rat (Acute): 2.07
Rat (Chronic Oral): 2.64
Fathead Minnow: 4.04
Respiratory Disease: Safe
Skin Sensitisation: Toxic
SR-ARE: Safe
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Safe
SR-p53: Safe

General Properties

Boiling Point: 314.52
Hydration Free Energy: -10.97
Log(D) at pH=7.4: 0.73
Log(P): 1.48
Log S: -1.7
Log(Vapor Pressure): -5.1
Melting Point: 143.93
pKa Acid: 7.97
pKa Basic: 2.76

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.8916
cGMP-dependent 3',5'-cyclic phosphodiesterase	O00408	PDE2A_HUMAN	Homo sapiens	3	0.8874
Pheromone-binding protein ASP1	Q9U9J6	Q9U9J6_APIME	Apis mellifera	3	0.8856
Norsolorinic acid synthase	Q12053	AFLC_ASPPU	Aspergillus parasiticus	3	0.8808
Mycinamicin III 3''-O-methyltransferase	Q49492	MYCF_MICGR	Micromonospora griseorubida	2	0.8715
Pheromone-binding protein ASP1	Q9U9J6	Q9U9J6_APIME	Apis mellifera	3	0.8482
Epoxide hydrolase	Q41415	Q41415_SOLTU	Solanum tuberosum	3	0.8368
Acetylcholine-binding protein	P58154	ACHP_LYMST	Lymnaea stagnalis	3	0.8295
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.8245
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.8108
Pheromone-binding protein ASP1	Q9U9J6	Q9U9J6_APIME	Apis mellifera	3	0.7981
Albumin	P02768	ALBU_HUMAN	Homo sapiens	3	0.7956
Mycinamicin III 3''-O-methyltransferase	Q49492	MYCF_MICGR	Micromonospora griseorubida	2	0.7936
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase	Q9TQS6	DHDH_MACFA	Macaca fascicularis	3	0.7848
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.7834
Phospholipase A2, major isoenzyme	P00592	PA21B_PIG	Sus scrofa	3	0.7715
Acetylcholinesterase	P04058	ACES_TETCF	Tetronarce californica	3	0.7711
Gag-Pol polyprotein	P0C6F2	POL_HV1LW	Human immunodeficiency virus type 1 group M subtype B	3	0.7691
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7546
Phenylalanine-4-hydroxylase	P00439	PH4H_HUMAN	Homo sapiens	3	0.7539
Nitric oxide synthase oxygenase	O34453	NOSO_BACSU	Bacillus subtilis	3	0.7504
Lethal(3)malignant brain tumor-like protein 1	Q9Y468	LMBL1_HUMAN	Homo sapiens	3	0.7499
Cystathionine gamma-synthase	P56069	METB_HELPY	Helicobacter pylori	3	0.7483
Peptidyl-prolyl cis-trans isomerase FKBP5	Q13451	FKBP5_HUMAN	Homo sapiens	3	0.7478
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7435
Nitric oxide synthase oxygenase	O34453	NOSO_BACSU	Bacillus subtilis	3	0.7407
NADPH dehydrogenase 1	Q02899	OYE1_SACPS	Saccharomyces pastorianus	3	0.7378
cGMP-inhibited 3',5'-cyclic phosphodiesterase 3B	Q13370	PDE3B_HUMAN	Homo sapiens	3	0.7336
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.7327
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7327
Tetracycline repressor protein class H	P51561	TETR8_PASMD	Pasteurella multocida	2	0.7282
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7280
Mitochondrial poly(A) polymerase	F1NBW0	F1NBW0_CHICK	Gallus gallus	2	0.7265
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7262
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	3	0.7240
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1	P04191	AT2A1_RABIT	Oryctolagus cuniculus	3	0.7228
Abscisic acid receptor PYL3	Q9SSM7	PYL3_ARATH	Arabidopsis thaliana	2	0.7188
Serine/threonine-protein kinase PLK1	P53350	PLK1_HUMAN	Homo sapiens	3	0.7169
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	3	0.7166
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7159
Vitamin D-binding protein	P02774	VTDB_HUMAN	Homo sapiens	2	0.7139
Acetylcholinesterase	P04058	ACES_TETCF	Tetronarce californica	3	0.7129
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.7121
Dual specificity mitogen-activated protein kinase kinase 1	Q02750	MP2K1_HUMAN	Homo sapiens	3	0.7119
Deoxycytidine kinase	P27707	DCK_HUMAN	Homo sapiens	3	0.7085
5-methyltetrahydropteroyltriglutamate--homocysteine methyltransferase 1	O50008	METE1_ARATH	Arabidopsis thaliana	2	0.7085
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7018
Ribonuclease J	H9CZL7	H9CZL7_DEIRD	Deinococcus radiodurans	3	0.7012
Phospholipase A2, major isoenzyme	P00592	PA21B_PIG	Sus scrofa	3	0.7012
Lactoylglutathione lyase	Q9CPU0	LGUL_MOUSE	Mus musculus	2	0.7008

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