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Makisterone C

Family: Plantae - Malvaceae
Kingdom: Plantae
Class: Steroid
- Subclass: Ecdysteroid

Canonical Smiles	CC[C@@H](C(O)(C)C)C[C@H]([C@@]([C@H]1CC[C@@]2([C@]1(C)CC[C@H]1C2=CC(=O)[C@H]2[C@]1(C)C[C@H](O)[C@@H](C2)O)O)(O)C)O
InChI	InChI=1S/C29H48O7/c1-7-16(25(2,3)34)12-24(33)28(6,35)23-9-11-29(36)18-13-20(30)19-14-21(31)22(32)15-26(19,4)17(18)8-10-27(23,29)5/h13,16-17,19,21-24,31-36H,7-12,14-15H2,1-6H3/t16-,17+,19+,21-,22+,23+,24-,26-,27-,28-,29-/m1/s1
InChIKey	CIQDSODCPIIBBH-RUVATRSJSA-N
Formula	C₂₉H₄₈O₇
HBA	7
HBD	6
MW	508.7
Rotatable Bonds	6
TPSA	138.45
LogP	2.49
Number Rings	4
Number Aromatic Rings	0
Heavy Atom Count	36
Formal Charge	0
Fraction CSP3	0.9
Exact Mass	508.34
Number of Lipinski Rule Violations	2

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Sida spinosa	Malvaceae	Plantae	108380

Showing of synonyms

Darwish FM, Reinecke MG (2003). Ecdysteroids and other constituents from Sida spinosa L. Phytochemistry,2003,62(8),1179-1184. [View] [PubMed]

Pubchem: 24984905

Cas: 19974-41-5

Zinc: ZINC000084740021

Nmrshiftdb2: 60028925

Chembl: CHEMBL2087159

No compound-protein relationship available.

SMILES: C1CCC(C12)CCC3C2=CC(=O)C4C3CCCC4

Level: 0

Mol. Weight: 508.7 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -5.04
Human Oral Bioavailability 20%: Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -5.18
Human Oral Bioavailability 50%: Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Substrate
Skin Permeability: -1.33

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.65
Plasma Protein Binding: 81.24
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: 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: 2.91
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Toxic
Avian: Safe
Bee: Toxic
Bioconcentration Factor: -3.32
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Safe
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 0.29
Liver Injury II: Toxic
hERG Blockers: Toxic
Daphnia Maga: 5.05
Micronucleos: Safe
NR-AhR: Safe
NR-AR: Safe
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: -242.71
Rat (Acute): 4.96
Rat (Chronic Oral): 2.31
Fathead Minnow: 3.72
Respiratory Disease: Toxic
Skin Sensitisation: Safe
SR-ARE: Safe
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Safe
SR-p53: Safe

General Properties

Boiling Point: 516.36
Hydration Free Energy: -3.02
Log(D) at pH=7.4: 2.39
Log(P): 2.03
Log S: -2.84
Log(Vapor Pressure): -10.48
Melting Point: 188.84
pKa Acid: 6.92
pKa Basic: 6.58

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
3-alpha-hydroxysteroid dehydrogenase	P23457	DIDH_RAT	Rattus norvegicus	3	0.9235
3-alpha-hydroxysteroid dehydrogenase	P23457	DIDH_RAT	Rattus norvegicus	3	0.9235
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.8620
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.8620
Steroid C26-monooxygenase	P9WPP1	CP125_MYCTU	Mycobacterium tuberculosis	3	0.8374
Steroid C26-monooxygenase	P9WPP1	CP125_MYCTU	Mycobacterium tuberculosis	3	0.8374
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.8254
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.8254
Neocarzinostatin	P0A3R9	NCZS_STRCZ	Streptomyces carzinostaticus	3	0.8208
Neocarzinostatin	P0A3R9	NCZS_STRCZ	Streptomyces carzinostaticus	3	0.8208
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.7966
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.7966
Lactoylglutathione lyase	Q9CPU0	LGUL_MOUSE	Mus musculus	2	0.7939
Lactoylglutathione lyase	Q9CPU0	LGUL_MOUSE	Mus musculus	2	0.7939
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.7800
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.7800
Liver carboxylesterase 1	P23141	EST1_HUMAN	Homo sapiens	3	0.7362
Liver carboxylesterase 1	P23141	EST1_HUMAN	Homo sapiens	3	0.7362
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.7311
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.7311
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.7088
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.7088

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