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(3R,4R)-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-ANLVUFKYSA-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: 10420140

Cas: 32885-83-9

Nmrshiftdb2: 60061038

Chembl: CHEMBL444818

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: 42.69
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: 0.15
Biodegradation: Toxic
Carcinogenesis: Safe
Crustacean: Safe
Liver Injury I (DILI): Toxic
Eye Corrosion: Safe
Eye Irritation: Toxic
Maximum Tolerated Dose: -0.35
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 4.12
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: 1.16
Rat (Acute): 2.07
Rat (Chronic Oral): 2.63
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: 315.33
Hydration Free Energy: -10.98
Log(D) at pH=7.4: 0.74
Log(P): 1.53
Log S: -1.71
Log(Vapor Pressure): -5.1
Melting Point: 140.17
pKa Acid: 7.97
pKa Basic: 2.74

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Pheromone-binding protein ASP1	Q9U9J6	Q9U9J6_APIME	Apis mellifera	3	0.9151
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.8820
Norsolorinic acid synthase	Q12053	AFLC_ASPPU	Aspergillus parasiticus	3	0.8662
L-lactate dehydrogenase A chain	P04642	LDHA_RAT	Rattus norvegicus	3	0.8465
Nitric oxide synthase 3	P29474	NOS3_HUMAN	Homo sapiens	3	0.8316
Albumin	P02768	ALBU_HUMAN	Homo sapiens	3	0.8236
Photosynthetic reaction center cytochrome c subunit	P07173	CYCR_BLAVI	Blastochloris viridis	3	0.8164
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.8126
Biphenyl-2,3-diol 1,2-dioxygenase	P17297	BPHC_PSES1	Pseudomonas sp	3	0.8111
Transcriptional activator, LuxR/UhpA family of regulators	Q7NQP7	Q7NQP7_CHRVO	Chromobacterium violaceum	3	0.8021
Trichothecene 15-O-acetyltransferase TRI3	Q9C1B7	TRI3_FUSSP	Fusarium sporotrichioides	3	0.8016
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase	Q9TQS6	DHDH_MACFA	Macaca fascicularis	3	0.8012
Acetylcholine-binding protein	P58154	ACHP_LYMST	Lymnaea stagnalis	3	0.7969
Acetylcholinesterase	P04058	ACES_TETCF	Tetronarce californica	3	0.7965
Biphenyl-2,3-diol 1,2-dioxygenase	P17297	BPHC_PSES1	Pseudomonas sp	3	0.7964
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	3	0.7958
Lactose operon repressor	P03023	LACI_ECOLI	Escherichia coli	3	0.7883
cGMP-dependent 3',5'-cyclic phosphodiesterase	O00408	PDE2A_HUMAN	Homo sapiens	3	0.7772
Class 10 plant pathogenesis-related protein 2B	Q9LLQ2	P102B_LUPLU	Lupinus luteus	2	0.7768
Lactoylglutathione lyase	Q9CPU0	LGUL_MOUSE	Mus musculus	2	0.7737
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7712
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	Q05603	COBT_SALTY	Salmonella typhimurium	3	0.7696
Chloramphenicol acetyltransferase	P62577	CAT_ECOLX	Escherichia coli	2	0.7671
Pheromone-binding protein ASP1	Q9U9J6	Q9U9J6_APIME	Apis mellifera	3	0.7651
Lethal(3)malignant brain tumor-like protein 1	Q9Y468	LMBL1_HUMAN	Homo sapiens	3	0.7563
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	2	0.7529
NADPH dehydrogenase 1	Q02899	OYE1_SACPS	Saccharomyces pastorianus	3	0.7464
Abscisic acid receptor PYL3	Q9SSM7	PYL3_ARATH	Arabidopsis thaliana	2	0.7442
Calmodulin-1	P0DP29	CALM1_RAT	Rattus norvegicus	3	0.7418
Phenylalanine-4-hydroxylase	P00439	PH4H_HUMAN	Homo sapiens	3	0.7405
Nitric oxide synthase oxygenase	O34453	NOSO_BACSU	Bacillus subtilis	3	0.7398
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7370
Nitric oxide synthase oxygenase	O34453	NOSO_BACSU	Bacillus subtilis	3	0.7365
Acetylcholinesterase	P04058	ACES_TETCF	Tetronarce californica	3	0.7292
CmeR	Q7B8P6	Q7B8P6_CAMJU	Campylobacter jejuni	2	0.7290
L-lactate dehydrogenase A chain	P04642	LDHA_RAT	Rattus norvegicus	3	0.7289
Purine nucleoside phosphorylase DeoD-type	P0ABP8	DEOD_ECOLI	Escherichia coli	3	0.7282
RNA-dependent RNA polymerase	Q6A562	Q6A562_9VIRU	Thosea asigna virus	2	0.7279
cGMP-inhibited 3',5'-cyclic phosphodiesterase 3B	Q13370	PDE3B_HUMAN	Homo sapiens	3	0.7263
Gag-Pol polyprotein	P0C6F2	POL_HV1LW	Human immunodeficiency virus type 1 group M subtype B	3	0.7246
Sulfotransferase 2B1	O00204	ST2B1_HUMAN	Homo sapiens	2	0.7233
Mitochondrial poly(A) polymerase	F1NBW0	F1NBW0_CHICK	Gallus gallus	2	0.7229
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7225
Sulfotransferase 1A1	P50225	ST1A1_HUMAN	Homo sapiens	2	0.7218
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	2	0.7216
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	3	0.7150
Rhodopsin	P02699	OPSD_BOVIN	Bos taurus	2	0.7147
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7124
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7103
Ribonuclease J	H9CZL7	H9CZL7_DEIRD	Deinococcus radiodurans	3	0.7089
Gastrotropin	Q6IMW5	Q6IMW5_DANRE	Danio rerio	2	0.7081
Dihydropteroate synthase	Q81VW8	Q81VW8_BACAN	Bacillus anthracis	2	0.7077
5-methyltetrahydropteroyltriglutamate--homocysteine methyltransferase 1	O50008	METE1_ARATH	Arabidopsis thaliana	2	0.7075
Fatty acid-binding protein, liver	P80226	FABPL_CHICK	Gallus gallus	2	0.7074
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.7030
Pheromone-binding protein ASP1	Q9U9J6	Q9U9J6_APIME	Apis mellifera	3	0.7029
Succinate dehydrogenase flavoprotein subunit	P0AC41	SDHA_ECOLI	Escherichia coli	3	0.7024
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.7020
Reductase homolog	Q9ZGC1	Q9ZGC1_STRCY	Streptomyces cyanogenus	3	0.7018

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