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Cumambrin A

Family: Plantae - Asteraceae
Kingdom: Plantae
Class: Terpenoid
- Subclass: Sesquiterpene Lactone

Canonical Smiles	CC(=O)O[C@H]1C[C@@](C)(O)[C@H]2[C@@H]([C@@H]3[C@@H]1C(=C)C(=O)O3)C(=CC2)C
InChI	InChI=1S/C17H22O5/c1-8-5-6-11-13(8)15-14(9(2)16(19)22-15)12(21-10(3)18)7-17(11,4)20/h5,11-15,20H,2,6-7H2,1,3-4H3/t11-,12+,13+,14-,15-,17-/m1/s1
InChIKey	XMJROHDIQQOWTO-NRPXGKOBSA-N
Formula	C₁₇H₂₂O₅
HBA	5
HBD	1
MW	306.36
Rotatable Bonds	1
TPSA	72.83
LogP	1.75
Number Rings	3
Number Aromatic Rings	0
Heavy Atom Count	22
Formal Charge	0
Fraction CSP3	0.65
Exact Mass	306.15
Number of Lipinski Rule Violations	0

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Chrysanthemum coronarium	Asteraceae	Plantae	99038

Showing of synonyms

El-masry S, Abou-donia AHA, et al. (1984). Sesquiterpene lactones from Chrysanthemum coronarium. Phytochemistry,1984,23(12),2953-2954. [View]

Pubchem: 174867

Cas: 20482-33-1

Zinc: ZINC000004027543

Nmrshiftdb2: 60025467

Chembl: CHEMBL190755

Comptox: DTXSID80174450

CPRiL: 416551

SMILES: O=C(O1)C(=C)C(C1C23)CCCC3CC=C2

Level: 0

Mol. Weight: 306.36 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -4.63
Human Oral Bioavailability 20%: Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.61
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -2.5

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Penetrable
Fraction Unbound (Human): 0.58
Plasma Protein Binding: 46.88
Steady State Volume of Distribution: -

Metabolism

Breast Cancer Resistance Protein: Non-Inhibitor
CYP 1A2 Inhibitor: Inhibitor
CYP 1A2 Substrate: Non-Substrate
CYP 2C19 Inhibitor: Non-Inhibitor
CYP 2C19 Substrate: Non-Substrate
CYP 2C9 Inhibitor: Non-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: 10.46
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: 0.29
Biodegradation: Safe
Carcinogenesis: Toxic
Crustacean: Safe
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: -0.25
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 5.0
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: 0.24
Rat (Acute): 3.28
Rat (Chronic Oral): 1.76
Fathead Minnow: 3.92
Respiratory Disease: Safe
Skin Sensitisation: Toxic
SR-ARE: Safe
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Safe
SR-p53: Toxic

General Properties

Boiling Point: 351.17
Hydration Free Energy: -6.68
Log(D) at pH=7.4: 1.09
Log(P): 1.58
Log S: -3.05
Log(Vapor Pressure): -6.55
Melting Point: 161.57
pKa Acid: 8.42
pKa Basic: 5.25

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
CmeR	Q7B8P6	Q7B8P6_CAMJU	Campylobacter jejuni	3	0.9489
CmeR	Q7B8P6	Q7B8P6_CAMJU	Campylobacter jejuni	3	0.9489
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	3	0.9006
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	3	0.9006
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.8652
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.8652
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.8442
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.8442
Sulfotransferase 2A1	Q06520	ST2A1_HUMAN	Homo sapiens	3	0.8210
Sulfotransferase 2A1	Q06520	ST2A1_HUMAN	Homo sapiens	3	0.8210
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	3	0.7837
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	3	0.7837
Cytochrome P450 monooxygenase	Q5YNS8	Q5YNS8_NOCFA	Nocardia farcinica	3	0.7812
Cytochrome P450 monooxygenase	Q5YNS8	Q5YNS8_NOCFA	Nocardia farcinica	3	0.7812
Lactoylglutathione lyase	Q9CPU0	LGUL_MOUSE	Mus musculus	2	0.7759
Lactoylglutathione lyase	Q9CPU0	LGUL_MOUSE	Mus musculus	2	0.7759
Cytochrome P450 monooxygenase	Q5YNS8	Q5YNS8_NOCFA	Nocardia farcinica	3	0.7702
Cytochrome P450 monooxygenase	Q5YNS8	Q5YNS8_NOCFA	Nocardia farcinica	3	0.7702
Cytochrome P450 monooxygenase	Q5YNS8	Q5YNS8_NOCFA	Nocardia farcinica	3	0.7633
Cytochrome P450 monooxygenase	Q5YNS8	Q5YNS8_NOCFA	Nocardia farcinica	3	0.7633
Progesterone receptor	P06401	PRGR_HUMAN	Homo sapiens	3	0.7484
Progesterone receptor	P06401	PRGR_HUMAN	Homo sapiens	3	0.7484
Corticosteroid-binding globulin	P08185	CBG_HUMAN	Homo sapiens	3	0.7465
Corticosteroid-binding globulin	P08185	CBG_HUMAN	Homo sapiens	3	0.7465
Mineralocorticoid receptor	P08235	MCR_HUMAN	Homo sapiens	3	0.7455
Mineralocorticoid receptor	P08235	MCR_HUMAN	Homo sapiens	3	0.7455
Mineralocorticoid receptor	P08235	MCR_HUMAN	Homo sapiens	3	0.7421
Mineralocorticoid receptor	P08235	MCR_HUMAN	Homo sapiens	3	0.7421
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7411
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7411
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.7300
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.7300
Ferrochelatase, mitochondrial	P22830	HEMH_HUMAN	Homo sapiens	3	0.7218
Ferrochelatase, mitochondrial	P22830	HEMH_HUMAN	Homo sapiens	3	0.7218

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