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24-methylenecycloartanone

Family: Plantae - Euphorbiaceae
Kingdom: Plantae
Class: Terpenoid
- Subclass: Tetracyclic Triterpene

Canonical Smiles	C=C(C(C)C)CCC(C1CCC2(C1(C)CCC13C2CCC2C3(C1)CCC(=O)C2(C)C)C)C
InChI	InChI=1S/C31H50O/c1-20(2)21(3)9-10-22(4)23-13-15-29(8)25-12-11-24-27(5,6)26(32)14-16-30(24)19-31(25,30)18-17-28(23,29)7/h20,22-25H,3,9-19H2,1-2,4-8H3
InChIKey	AEAWOMODYBIREN-UHFFFAOYSA-N
Formula	C₃₁H₅₀O
HBA	1
HBD	0
MW	438.74
Rotatable Bonds	5
TPSA	17.07
LogP	8.62
Number Rings	5
Number Aromatic Rings	0
Heavy Atom Count	32
Formal Charge	0
Fraction CSP3	0.9
Exact Mass	438.39
Number of Lipinski Rule Violations	1

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Euphorbia pterococca	Euphorbiaceae	Plantae	1087778

Showing of synonyms

Benabdelaziz I, Gómez-Ruiz S, et al. (2018). New cycloartane-type ester triterpenes from Euphorbia pterococca and biological evaluation. Fitoterapia, 2018, 127, 271-278. [View] [PubMed]

Pubchem: 634880

Nmrshiftdb2: 70125952

No compound-protein relationship available.

SMILES: C1CC(=O)CC(C1(C234)C2)CCC3C5C(CC4)CCC5

Level: 0

Mol. Weight: 438.74 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -4.75
Human Oral Bioavailability 20%: Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.65
Human Oral Bioavailability 50%: Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -2.79

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Penetrable
Fraction Unbound (Human): 2.37
Plasma Protein Binding: 42.35
Steady State Volume of Distribution: -

Metabolism

Breast Cancer Resistance Protein: 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: 6.89
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: 1.73
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Toxic
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 1.28
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 6.76
Micronucleos: Safe
NR-AhR: Safe
NR-AR: Toxic
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: -77.18
Rat (Acute): 2.2
Rat (Chronic Oral): 1.73
Fathead Minnow: 5.0
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: 417.14
Hydration Free Energy: -2.82
Log(D) at pH=7.4: 7.16
Log(P): 8.53
Log S: -6.83
Log(Vapor Pressure): -7.39
Melting Point: 158.16
pKa Acid: 11.91
pKa Basic: 7.43

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Beta-lactoglobulin	P02754	LACB_BOVIN	Bos taurus	3	0.9330
Cholesterol side-chain cleavage enzyme, mitochondrial	P05108	CP11A_HUMAN	Homo sapiens	3	0.9169
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.9083
Mycinamicin III 3''-O-methyltransferase	Q49492	MYCF_MICGR	Micromonospora griseorubida	2	0.8995
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.8942
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	3	0.8927
Mycinamicin III 3''-O-methyltransferase	Q49492	MYCF_MICGR	Micromonospora griseorubida	2	0.8856
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.8798
Beta-elicitin cryptogein	P15570	ELIB_PHYCR	Phytophthora cryptogea	4	0.8749
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	3	0.8646
Retinol-binding protein 1	P02696	RET1_RAT	Rattus norvegicus	3	0.8604
Retinol-binding protein 2	P50120	RET2_HUMAN	Homo sapiens	3	0.8589
Cytochrome P450 monooxygenase	Q5YNS8	Q5YNS8_NOCFA	Nocardia farcinica	3	0.8490
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	3	0.8445
Probable NDP-rhamnosyltransferase	Q9ALM8	Q9ALM8_SACSN	Saccharopolyspora spinosa	3	0.8289
Protein BRASSINOSTEROID INSENSITIVE 1	O22476	BRI1_ARATH	Arabidopsis thaliana	3	0.8247
Progesterone receptor	P06401	PRGR_HUMAN	Homo sapiens	3	0.8201
Aldo-keto reductase family 1 member C1	Q04828	AK1C1_HUMAN	Homo sapiens	3	0.8198
Steroid C26-monooxygenase	P9WPP1	CP125_MYCTU	Mycobacterium tuberculosis	3	0.8121
Abscisic acid receptor PYL3	Q9SSM7	PYL3_ARATH	Arabidopsis thaliana	3	0.8096
Vitamin D(3) 25-hydroxylase	C4B644	CPVDH_PSEAH	Pseudonocardia autotrophica	3	0.8059
Protein BRASSINOSTEROID INSENSITIVE 1	O22476	BRI1_ARATH	Arabidopsis thaliana	3	0.8026
Protein BRASSINOSTEROID INSENSITIVE 1	O22476	BRI1_ARATH	Arabidopsis thaliana	3	0.8024
Cytochrome P450 monooxygenase	Q5YNS8	Q5YNS8_NOCFA	Nocardia farcinica	3	0.7954
Lactoylglutathione lyase	Q9CPU0	LGUL_MOUSE	Mus musculus	2	0.7904
Retinol dehydratase	Q26490	Q26490_SPOFR	Spodoptera frugiperda	3	0.7870
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1	P04191	AT2A1_RABIT	Oryctolagus cuniculus	3	0.7812
Abscisic acid receptor PYR1	O49686	PYR1_ARATH	Arabidopsis thaliana	3	0.7651
Retinol-binding protein 2	P50120	RET2_HUMAN	Homo sapiens	3	0.7619
Beta-1 adrenergic receptor	P07700	ADRB1_MELGA	Meleagris gallopavo	3	0.7594
Ferrochelatase, mitochondrial	P22830	HEMH_HUMAN	Homo sapiens	3	0.7585
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	2	0.7570
CmeR	Q7B8P6	Q7B8P6_CAMJU	Campylobacter jejuni	2	0.7557
Rhodopsin	P02699	OPSD_BOVIN	Bos taurus	3	0.7556
3-alpha-hydroxysteroid dehydrogenase	P23457	DIDH_RAT	Rattus norvegicus	2	0.7523
Beta-1 adrenergic receptor	P07700	ADRB1_MELGA	Meleagris gallopavo	3	0.7463
Beta-lactoglobulin	P02754	LACB_BOVIN	Bos taurus	3	0.7431
Progesterone receptor	P06401	PRGR_HUMAN	Homo sapiens	3	0.7415
Enoyl-[acyl-carrier-protein] reductase [NADH]	P9WGR1	INHA_MYCTU	Mycobacterium tuberculosis	2	0.7400
3-ketosteroid dehydrogenase	Q9RA02	Q9RA02_RHOER	Rhodococcus erythropolis	2	0.7389
Reaction center protein L chain	P0C0Y7	RCEH_RHOSH	Rhodobacter sphaeroides	2	0.7373
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1	P04191	AT2A1_RABIT	Oryctolagus cuniculus	2	0.7371
Androgen receptor	P10275	ANDR_HUMAN	Homo sapiens	3	0.7350
Photosynthetic reaction center cytochrome c subunit	P07173	CYCR_BLAVI	Blastochloris viridis	2	0.7303
Vitamin D3 receptor	P13053	VDR_RAT	Rattus norvegicus	3	0.7290
Lanosterol synthase	P48449	ERG7_HUMAN	Homo sapiens	3	0.7287
Steroid C26-monooxygenase	P9WPP1	CP125_MYCTU	Mycobacterium tuberculosis	2	0.7282
Retinol-binding protein 1	P02696	RET1_RAT	Rattus norvegicus	3	0.7263
17-beta-hydroxysteroid dehydrogenase type 1	P14061	DHB1_HUMAN	Homo sapiens	2	0.7252
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	2	0.7238
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	2	0.7196
Vitamin D3 receptor	P13053	VDR_RAT	Rattus norvegicus	3	0.7192
Beta-1 adrenergic receptor	P07700	ADRB1_MELGA	Meleagris gallopavo	3	0.7150
Fatty acid-binding protein 10-A, liver basic	Q9I8L5	FA10A_DANRE	Danio rerio	2	0.7144
Abscisic acid receptor PYL2	O80992	PYL2_ARATH	Arabidopsis thaliana	2	0.7103
Retinoic acid receptor RXR-alpha	P19793	RXRA_HUMAN	Homo sapiens	3	0.7099
Cholesterol side-chain cleavage enzyme, mitochondrial	P00189	CP11A_BOVIN	Bos taurus	3	0.7088
Retinol-binding protein 1	P09455	RET1_HUMAN	Homo sapiens	3	0.7068
CmeR	Q7B8P6	Q7B8P6_CAMJU	Campylobacter jejuni	2	0.7058
Acetylcholinesterase	P21836	ACES_MOUSE	Mus musculus	2	0.7053
11-beta-hydroxysteroid dehydrogenase 1	P28845	DHI1_HUMAN	Homo sapiens	3	0.7052
Photosynthetic reaction center cytochrome c subunit	P07173	CYCR_BLAVI	Blastochloris viridis	2	0.7036

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