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Kulactone

Family: Plantae - Meliaceae
Kingdom: Plantae
Class: Terpenoid
- Subclass: Triterpenoid

Canonical Smiles	CC(=CCC[C@H]1C(=O)O[C@@H]2[C@@H]1[C@]1(C)CC[C@H]3C(=CC[C@@H]4[C@]3(C)CCC(=O)C4(C)C)[C@]1(C2)C)C
InChI	InChI=1S/C30H44O3/c1-18(2)9-8-10-19-25-22(33-26(19)32)17-30(7)21-11-12-23-27(3,4)24(31)14-15-28(23,5)20(21)13-16-29(25,30)6/h9,11,19-20,22-23,25H,8,10,12-17H2,1-7H3/t19-,20+,22+,23+,25-,28-,29+,30-/m1/s1
InChIKey	ZIVZDNPCRURPNL-QCWHEMHRSA-N
Formula	C₃₀H₄₄O₃
HBA	3
HBD	0
MW	452.68
Rotatable Bonds	3
TPSA	43.37
LogP	7.06
Number Rings	5
Number Aromatic Rings	0
Heavy Atom Count	33
Formal Charge	0
Fraction CSP3	0.8
Exact Mass	452.33
Number of Lipinski Rule Violations	1

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Melia volkensii	Meliaceae	Plantae	643111

Showing of synonyms

Cantrell CL, Rajab MS, et al. (1999). Antimycobacterial triterpenes from Melia volkensii.. Journal of Natural Products,1999,62(4),546-548. [View] [PubMed]

Pubchem: 15560423

Cas: 22611-36-5

Nmrshiftdb2: 60070907

Chembl: CHEMBL464664

No compound-protein relationship available.

SMILES: C1C(=O)OC2CC(C3C12)C=4C(CC3)C5C(CC4)CC(=O)CC5

Level: 0

Mol. Weight: 452.68 g/mol

Antimycobacterial

Absorption

Caco-2 (logPapp): -4.82
Human Oral Bioavailability 20%: Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.69
Human Oral Bioavailability 50%: Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -1.69

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Penetrable
Fraction Unbound (Human): 2.23
Plasma Protein Binding: 90.61
Steady State Volume of Distribution: -

Metabolism

Breast Cancer Resistance Protein: Non-Inhibitor
CYP 1A2 Inhibitor: Non-Inhibitor
CYP 1A2 Substrate: Substrate
CYP 2C19 Inhibitor: Non-Inhibitor
CYP 2C19 Substrate: 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: Substrate
OATP1B1: Non-Inhibitor
OATP1B3: Non-Inhibitor

Excretion

Clearance: 10.08
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: 0.56
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 0.65
Liver Injury II: Toxic
hERG Blockers: Toxic
Daphnia Maga: 6.6
Micronucleos: Safe
NR-AhR: Safe
NR-AR: Toxic
NR-AR-LBD: Safe
NR-Aromatase: Safe
NR-ER: Safe
NR-ER-LBD: Safe
NR-GR: Toxic
NR-PPAR-gamma: Safe
NR-TR: Safe
T. Pyriformis: -117.05
Rat (Acute): 1.85
Rat (Chronic Oral): 1.56
Fathead Minnow: 3.97
Respiratory Disease: Toxic
Skin Sensitisation: Toxic
SR-ARE: Toxic
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Safe
SR-p53: Safe

General Properties

Boiling Point: 487.72
Hydration Free Energy: -2.56
Log(D) at pH=7.4: 6.0
Log(P): 6.68
Log S: -6.83
Log(Vapor Pressure): -7.95
Melting Point: 179.4
pKa Acid: 10.91
pKa Basic: 5.84

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	0.8792
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	3	0.8792
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	3	0.8757
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	3	0.8757
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.7919
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.7919
Pentaerythritol tetranitrate reductase	P71278	P71278_ENTCL	Enterobacter cloacae	2	0.7702
Pentaerythritol tetranitrate reductase	P71278	P71278_ENTCL	Enterobacter cloacae	2	0.7702
Protein BRASSINOSTEROID INSENSITIVE 1	O22476	BRI1_ARATH	Arabidopsis thaliana	3	0.7591
Protein BRASSINOSTEROID INSENSITIVE 1	O22476	BRI1_ARATH	Arabidopsis thaliana	3	0.7591
Lactoylglutathione lyase	Q9CPU0	LGUL_MOUSE	Mus musculus	2	0.7555
Lactoylglutathione lyase	Q9CPU0	LGUL_MOUSE	Mus musculus	2	0.7555
Protein BRASSINOSTEROID INSENSITIVE 1	O22476	BRI1_ARATH	Arabidopsis thaliana	3	0.7554
Protein BRASSINOSTEROID INSENSITIVE 1	O22476	BRI1_ARATH	Arabidopsis thaliana	3	0.7554
Retinol-binding protein 1	P09455	RET1_HUMAN	Homo sapiens	3	0.7366
Retinol-binding protein 1	P09455	RET1_HUMAN	Homo sapiens	3	0.7366
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	2	0.7364
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	2	0.7364
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7347
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7347
Transcriptional activator, LuxR/UhpA family of regulators	Q7NQP7	Q7NQP7_CHRVO	Chromobacterium violaceum	2	0.7309
Transcriptional activator, LuxR/UhpA family of regulators	Q7NQP7	Q7NQP7_CHRVO	Chromobacterium violaceum	2	0.7309
Pentaerythritol tetranitrate reductase	P71278	P71278_ENTCL	Enterobacter cloacae	3	0.7298
Pentaerythritol tetranitrate reductase	P71278	P71278_ENTCL	Enterobacter cloacae	3	0.7298
Mycinamicin III 3''-O-methyltransferase	Q49492	MYCF_MICGR	Micromonospora griseorubida	2	0.7245
Mycinamicin III 3''-O-methyltransferase	Q49492	MYCF_MICGR	Micromonospora griseorubida	2	0.7245
Nuclear receptor subfamily 1 group I member 2	O75469	NR1I2_HUMAN	Homo sapiens	3	0.7181
Nuclear receptor subfamily 1 group I member 2	O75469	NR1I2_HUMAN	Homo sapiens	3	0.7181
Mineralocorticoid receptor	P08235	MCR_HUMAN	Homo sapiens	4	0.7121
Mineralocorticoid receptor	P08235	MCR_HUMAN	Homo sapiens	4	0.7121
Beta-1 adrenergic receptor	P07700	ADRB1_MELGA	Meleagris gallopavo	3	0.7116
Beta-1 adrenergic receptor	P07700	ADRB1_MELGA	Meleagris gallopavo	3	0.7116
Retinol-binding protein 1	P02696	RET1_RAT	Rattus norvegicus	3	0.7081
Retinol-binding protein 1	P02696	RET1_RAT	Rattus norvegicus	3	0.7081

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