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Madiaol

Family: Plantae - Asteraceae
Kingdom: Plantae
Class: Terpenoid
- Subclass: Diterpenoid

Canonical Smiles	OC[C@@H](C1(C)CCC(O1)(O)C(=C)CCC1C(C)(C)CCCC1(C)O)O
InChI	InChI=1S/C20H36O5/c1-14(20(24)12-11-19(5,25-20)16(22)13-21)7-8-15-17(2,3)9-6-10-18(15,4)23/h15-16,21-24H,1,6-13H2,2-5H3/t15?,16-,18?,19?,20?/m0/s1
InChIKey	RIFYQCYKHQDXDN-OHJGJUJKSA-N
Formula	C₂₀H₃₆O₅
HBA	5
HBD	4
MW	356.5
Rotatable Bonds	6
TPSA	90.15
LogP	2.51
Number Rings	2
Number Aromatic Rings	0
Heavy Atom Count	25
Formal Charge	0
Fraction CSP3	0.9
Exact Mass	356.26
Number of Lipinski Rule Violations	0

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Madia anomala	Asteraceae	Plantae	71817
2	Madia capitata	Asteraceae	Plantae	576756
3	Madia citrigracilis	Asteraceae	Plantae	4253
4	Madia dissitiflora	Asteraceae	Plantae	907201
5	Madia elegans	Asteraceae	Plantae	4255

Showing of synonyms

Wollenweber E, Dörr M, et al. (2003). Flavonoids and terpenoids from the resinous exudates of Madia species (Asteraceae, Helenieae). Zeitschrift fur Naturforschung C,2003,58,153-160. [View] [PubMed]

Pubchem: 162816892

Nmrshiftdb2: 70054845

No compound-protein relationship available.

SMILES: O1CCCC1C(=C)CCC2CCCCC2

Level: 1

Mol. Weight: 356.5 g/mol

SMILES: C1CCCCC1

Level: 0

Mol. Weight: 356.5 g/mol

SMILES: C1CCOC1

Level: 0

Mol. Weight: 356.5 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -4.92
Human Oral Bioavailability 20%: Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.52
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -2.18

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Penetrable
Fraction Unbound (Human): 0.57
Plasma Protein Binding: 29.78
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: 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: 6.02
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: -0.18
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Safe
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: -0.55
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 4.38
Micronucleos: Safe
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: -0.34
Rat (Acute): 2.53
Rat (Chronic Oral): 2.03
Fathead Minnow: 3.6
Respiratory Disease: Toxic
Skin Sensitisation: Toxic
SR-ARE: Safe
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Safe
SR-p53: Safe

General Properties

Boiling Point: 391.05
Hydration Free Energy: -11.11
Log(D) at pH=7.4: 2.0
Log(P): 2.37
Log S: -2.82
Log(Vapor Pressure): -7.84
Melting Point: 112.02
pKa Acid: 8.42
pKa Basic: 7.79

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	3	0.8813
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	3	0.8813
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	3	0.8640
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	3	0.8640
Beta-glucosidase 1A	Q25BW5	BGL1A_PHACH	Phanerodontia chrysosporium	3	0.8216
Beta-glucosidase 1A	Q25BW5	BGL1A_PHACH	Phanerodontia chrysosporium	3	0.8216
CmeR	Q7B8P6	Q7B8P6_CAMJU	Campylobacter jejuni	3	0.8100
CmeR	Q7B8P6	Q7B8P6_CAMJU	Campylobacter jejuni	3	0.8100
Gastrotropin	P51161	FABP6_HUMAN	Homo sapiens	3	0.7953
Gastrotropin	P51161	FABP6_HUMAN	Homo sapiens	3	0.7953
Prolyl tripeptidyl peptidase	Q7MUW6	PTP_PORGI	Porphyromonas gingivalis	3	0.7913
Prolyl tripeptidyl peptidase	Q7MUW6	PTP_PORGI	Porphyromonas gingivalis	3	0.7913
Neocarzinostatin	P0A3R9	NCZS_STRCZ	Streptomyces carzinostaticus	3	0.7794
Neocarzinostatin	P0A3R9	NCZS_STRCZ	Streptomyces carzinostaticus	3	0.7794
Integrin alpha-L	P20701	ITAL_HUMAN	Homo sapiens	3	0.7663
Integrin alpha-L	P20701	ITAL_HUMAN	Homo sapiens	3	0.7663
Sulfotransferase 2B1	O00204	ST2B1_HUMAN	Homo sapiens	2	0.7606
Sulfotransferase 2B1	O00204	ST2B1_HUMAN	Homo sapiens	2	0.7606
Nuclear receptor ROR-beta	P45446	RORB_RAT	Rattus norvegicus	2	0.7598
Nuclear receptor ROR-beta	P45446	RORB_RAT	Rattus norvegicus	2	0.7598
Lactoylglutathione lyase	Q9CPU0	LGUL_MOUSE	Mus musculus	2	0.7454
Lactoylglutathione lyase	Q9CPU0	LGUL_MOUSE	Mus musculus	2	0.7454
Aldo-keto reductase family 1 member C1	Q04828	AK1C1_HUMAN	Homo sapiens	2	0.7453
Aldo-keto reductase family 1 member C1	Q04828	AK1C1_HUMAN	Homo sapiens	2	0.7453
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	3	0.7392
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	3	0.7392
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	2	0.7216
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	2	0.7216
Vitamin D-binding protein	P02774	VTDB_HUMAN	Homo sapiens	2	0.7212
Vitamin D-binding protein	P02774	VTDB_HUMAN	Homo sapiens	2	0.7212
11-beta-hydroxysteroid dehydrogenase 1	P28845	DHI1_HUMAN	Homo sapiens	3	0.7209
11-beta-hydroxysteroid dehydrogenase 1	P28845	DHI1_HUMAN	Homo sapiens	3	0.7209
Fatty acid-binding protein, liver	P80226	FABPL_CHICK	Gallus gallus	3	0.7195
Fatty acid-binding protein, liver	P80226	FABPL_CHICK	Gallus gallus	3	0.7195
Laminarinase	Q9WXN1	Q9WXN1_THEMA	Thermotoga maritima	3	0.7166
Laminarinase	Q9WXN1	Q9WXN1_THEMA	Thermotoga maritima	3	0.7166
Transcriptional activator, LuxR/UhpA family of regulators	Q7NQP7	Q7NQP7_CHRVO	Chromobacterium violaceum	3	0.7163
Transcriptional activator, LuxR/UhpA family of regulators	Q7NQP7	Q7NQP7_CHRVO	Chromobacterium violaceum	3	0.7163
N-alpha-acetyltransferase 50	Q9GZZ1	NAA50_HUMAN	Homo sapiens	3	0.7140
N-alpha-acetyltransferase 50	Q9GZZ1	NAA50_HUMAN	Homo sapiens	3	0.7140
Nuclear receptor subfamily 1 group I member 2	O75469	NR1I2_HUMAN	Homo sapiens	3	0.7096
Nuclear receptor subfamily 1 group I member 2	O75469	NR1I2_HUMAN	Homo sapiens	3	0.7096
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	3	0.7087
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	3	0.7087
Cytochrome P450 monooxygenase	Q5YNS8	Q5YNS8_NOCFA	Nocardia farcinica	3	0.7067
Cytochrome P450 monooxygenase	Q5YNS8	Q5YNS8_NOCFA	Nocardia farcinica	3	0.7067
Transcriptional activator, LuxR/UhpA family of regulators	Q7NQP7	Q7NQP7_CHRVO	Chromobacterium violaceum	3	0.7049
Transcriptional activator, LuxR/UhpA family of regulators	Q7NQP7	Q7NQP7_CHRVO	Chromobacterium violaceum	3	0.7049
Methionine aminopeptidase 1	P53582	MAP11_HUMAN	Homo sapiens	3	0.7043
Methionine aminopeptidase 1	P53582	MAP11_HUMAN	Homo sapiens	3	0.7043
Retinaldehyde-binding protein 1	P12271	RLBP1_HUMAN	Homo sapiens	4	0.7038
Retinaldehyde-binding protein 1	P12271	RLBP1_HUMAN	Homo sapiens	4	0.7038

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