Cycloeucalenol - Compound Card

Cycloeucalenol

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Cycloeucalenol

Structure
Zoomed Structure
  • Family: Plantae - Euphorbiaceae
  • Kingdom: Plantae
  • Class: Steroid
    • Subclass: Sterol
Canonical Smiles C=C(C(C)C)CC[C@H]([C@H]1CC[C@@]2([C@]1(C)CC[C@@]13[C@H]2CC[C@@H]2[C@]3(C1)CC[C@@H]([C@H]2C)O)C)C
InChI InChI=1S/C30H50O/c1-19(2)20(3)8-9-21(4)23-12-14-28(7)26-11-10-24-22(5)25(31)13-15-29(24)18-30(26,29)17-16-27(23,28)6/h19,21-26,31H,3,8-18H2,1-2,4-7H3/t21-,22+,23-,24+,25+,26+,27-,28+,29-,30+/m1/s1
InChIKey HUNLTIZKNQDZEI-PGFZVWMDSA-N
Formula C30H50O
HBA 1
HBD 1
MW 426.73
Rotatable Bonds 5
TPSA 20.23
LogP 8.02
Number Rings 5
Number Aromatic Rings 0
Heavy Atom Count 31
Formal Charge 0
Fraction CSP3 0.93
Exact Mass 426.39
Number of Lipinski Rule Violations 1
# Species Family Kingdom NCBI Taxonomy ID
1 Euphorbia guyoniana Euphorbiaceae Plantae 1138347
2 Euphorbia bupleuroides Euphorbiaceae Plantae 1532838

Showing of synonyms

  • Haba H, Lavaud C, et al. (2007). Diterpenoids and triterpenoids from Euphorbia guyoniana. Phytochemistry,2007,68,1255-1260. [View] [PubMed]
  • Aichour S, Haba H, et al. (2014). Terpenoids and other constituents from Euphorbia bupleuroides. Phytochemistry,2014,10,198-203. [View]
Pubchem: 101690
Kegg Ligand: C02141
Chebi: 16653
Nmrshiftdb2: 60018455
CPRiL: 73603
Structure

SMILES: C1CCCC(C1(C234)C2)CCC3C5C(CC4)CCC5

Level: 0

Mol. Weight: 426.73 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.81
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.52
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-3.18

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.87
Plasma Protein Binding
89.52
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
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
Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
8.39
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.54
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
1.4
Liver Injury II
Toxic
hERG Blockers
Toxic
Daphnia Maga
6.47
Micronucleos
Safe
NR-AhR
Safe
NR-AR
Toxic
NR-AR-LBD
Toxic
NR-Aromatase
Safe
NR-ER
Safe
NR-ER-LBD
Safe
NR-GR
Safe
NR-PPAR-gamma
Safe
NR-TR
Toxic
T. Pyriformis
-62.37
Rat (Acute)
2.44
Rat (Chronic Oral)
1.94
Fathead Minnow
3.92
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
408.02
Hydration Free Energy
-2.89
Log(D) at pH=7.4
7.17
Log(P)
8.49
Log S
-7.01
Log(Vapor Pressure)
-7.89
Melting Point
172.34
pKa Acid
12.97
pKa Basic
7.93
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.9322
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.9322
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.8890
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.8890
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8563
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8563
Steroid C26-monooxygenase P9WPP1 CP125_MYCTU Mycobacterium tuberculosis 3 0.8384
Steroid C26-monooxygenase P9WPP1 CP125_MYCTU Mycobacterium tuberculosis 3 0.8384
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8348
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8348
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8278
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8278
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 3 0.8185
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 3 0.8185
Retinol-binding protein 1 P02696 RET1_RAT Rattus norvegicus 3 0.8035
Retinol-binding protein 1 P02696 RET1_RAT Rattus norvegicus 3 0.8035
Gastrotropin P51161 FABP6_HUMAN Homo sapiens 3 0.7946
Gastrotropin P51161 FABP6_HUMAN Homo sapiens 3 0.7946
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 3 0.7940
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 3 0.7940
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7830
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7830
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7799
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7799
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7743
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7743
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7736
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7736
Beta-elicitin cryptogein P15570 ELIB_PHYCR Phytophthora cryptogea 3 0.7711
Beta-elicitin cryptogein P15570 ELIB_PHYCR Phytophthora cryptogea 3 0.7711
Aromatase P11511 CP19A_HUMAN Homo sapiens 3 0.7677
Aromatase P11511 CP19A_HUMAN Homo sapiens 3 0.7677
Protein BRASSINOSTEROID INSENSITIVE 1 O22476 BRI1_ARATH Arabidopsis thaliana 3 0.7663
Protein BRASSINOSTEROID INSENSITIVE 1 O22476 BRI1_ARATH Arabidopsis thaliana 3 0.7663
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 3 0.7618
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 3 0.7618
Nuclear receptor subfamily 1 group I member 3 O35627 NR1I3_MOUSE Mus musculus 3 0.7596
Nuclear receptor subfamily 1 group I member 3 O35627 NR1I3_MOUSE Mus musculus 3 0.7596
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7557
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7557
Protein BRASSINOSTEROID INSENSITIVE 1 O22476 BRI1_ARATH Arabidopsis thaliana 3 0.7533
Protein BRASSINOSTEROID INSENSITIVE 1 O22476 BRI1_ARATH Arabidopsis thaliana 3 0.7533
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.7508
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.7508
Protein BRASSINOSTEROID INSENSITIVE 1 O22476 BRI1_ARATH Arabidopsis thaliana 3 0.7447
Protein BRASSINOSTEROID INSENSITIVE 1 O22476 BRI1_ARATH Arabidopsis thaliana 3 0.7447
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 3 0.7400
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 3 0.7400
Retinol dehydratase Q26490 Q26490_SPOFR Spodoptera frugiperda 3 0.7339
Retinol dehydratase Q26490 Q26490_SPOFR Spodoptera frugiperda 3 0.7339
Sodium-dependent dopamine transporter Q7K4Y6 DAT_DROME Drosophila melanogaster 2 0.7168
Sodium-dependent dopamine transporter Q7K4Y6 DAT_DROME Drosophila melanogaster 2 0.7168
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7144
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7144
NPC intracellular cholesterol transporter 1 O15118 NPC1_HUMAN Homo sapiens 3 0.7104
NPC intracellular cholesterol transporter 1 O15118 NPC1_HUMAN Homo sapiens 3 0.7104
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 3 0.7056
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 3 0.7056

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