24-methylenecycloartanyl formate - Compound Card

24-methylenecycloartanyl formate

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24-methylenecycloartanyl formate

Structure
Zoomed Structure
  • Family: Plantae - Euphorbiaceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Triterpenoid
Canonical Smiles O=CO[C@H]1CC[C@]23[C@H](C1(C)C)CCC1[C@@]3(C2)CC[C@]2([C@@]1(C)CC[C@@H]2C(=C)CCCC(C)C)C
InChI InChI=1S/C31H50O2/c1-21(2)9-8-10-22(3)23-13-15-29(7)25-12-11-24-27(4,5)26(33-20-32)14-16-30(24)19-31(25,30)18-17-28(23,29)6/h20-21,23-26H,3,8-19H2,1-2,4-7H3/t23-,24+,25?,26+,28-,29+,30-,31+/m1/s1
InChIKey QEDQTNZVGXGFNQ-MSIUMDTJSA-N
Formula C31H50O2
HBA 2
HBD 0
MW 454.74
Rotatable Bonds 7
TPSA 26.3
LogP 8.35
Number Rings 5
Number Aromatic Rings 0
Heavy Atom Count 33
Formal Charge 0
Fraction CSP3 0.9
Exact Mass 454.38
Number of Lipinski Rule Violations 1
# Species Family Kingdom NCBI Taxonomy ID
1 Euphorbia retusa Euphorbiaceae Plantae 1091645

Showing of synonyms

  • Haba H, Lavaud C, et al. (2009). Diterpenoids and triterpenoids from Euphorbia retusa. Journal of Natural Products,2009,72(7),1258-1264. [View] [PubMed]
Pubchem: 162898922
Nmrshiftdb2: 60062695

No compound-protein relationship available.

Structure

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

Level: 0

Mol. Weight: 454.74 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.77
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.44
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.74

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
2.11
Plasma Protein Binding
92.87
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Inhibitor
CYP 1A2 Inhibitor
Non-Inhibitor
CYP 1A2 Substrate
Non-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
5.17
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
1.18
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.8
Liver Injury II
Toxic
hERG Blockers
Toxic
Daphnia Maga
7.47
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
-144.27
Rat (Acute)
2.54
Rat (Chronic Oral)
1.98
Fathead Minnow
4.19
Respiratory Disease
Safe
Skin Sensitisation
Toxic
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
445.59
Hydration Free Energy
-2.8
Log(D) at pH=7.4
7.61
Log(P)
9.28
Log S
-7.07
Log(Vapor Pressure)
-8.02
Melting Point
143.36
pKa Acid
11.46
pKa Basic
6.64
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.9096
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.9096
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8972
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8972
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8816
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8816
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8739
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8739
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8493
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8493
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.8345
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.8345
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8191
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8191
Protein BRASSINOSTEROID INSENSITIVE 1 O22476 BRI1_ARATH Arabidopsis thaliana 3 0.8005
Protein BRASSINOSTEROID INSENSITIVE 1 O22476 BRI1_ARATH Arabidopsis thaliana 3 0.8005
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7936
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7936
Vitamin D(3) 25-hydroxylase C4B644 CPVDH_PSEAH Pseudonocardia autotrophica 3 0.7812
Vitamin D(3) 25-hydroxylase C4B644 CPVDH_PSEAH Pseudonocardia autotrophica 3 0.7812
Protein BRASSINOSTEROID INSENSITIVE 1 O22476 BRI1_ARATH Arabidopsis thaliana 3 0.7750
Protein BRASSINOSTEROID INSENSITIVE 1 O22476 BRI1_ARATH Arabidopsis thaliana 3 0.7750
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7707
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7707
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7680
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7680
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7680
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7680
Beta-lactoglobulin P02754 LACB_BOVIN Bos taurus 3 0.7546
Beta-lactoglobulin P02754 LACB_BOVIN Bos taurus 3 0.7546
Protein BRASSINOSTEROID INSENSITIVE 1 O22476 BRI1_ARATH Arabidopsis thaliana 3 0.7544
Protein BRASSINOSTEROID INSENSITIVE 1 O22476 BRI1_ARATH Arabidopsis thaliana 3 0.7544
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7525
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7525
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 2 0.7495
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 2 0.7495
Retinol-binding protein 1 P02696 RET1_RAT Rattus norvegicus 3 0.7463
Retinol-binding protein 1 P02696 RET1_RAT Rattus norvegicus 3 0.7463
Aldo-keto reductase family 1 member C1 Q04828 AK1C1_HUMAN Homo sapiens 2 0.7423
Aldo-keto reductase family 1 member C1 Q04828 AK1C1_HUMAN Homo sapiens 2 0.7423
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 3 0.7344
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 3 0.7344
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7283
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7283
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7212
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7212
Steroid C26-monooxygenase P9WPP1 CP125_MYCTU Mycobacterium tuberculosis 3 0.7203
Steroid C26-monooxygenase P9WPP1 CP125_MYCTU Mycobacterium tuberculosis 3 0.7203
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7187
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7187
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 2 0.7153
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 2 0.7153
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7136
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7136
Beta-lactoglobulin P02754 LACB_BOVIN Bos taurus 3 0.7117
Beta-lactoglobulin P02754 LACB_BOVIN Bos taurus 3 0.7117
Methylketone synthase I E0YCS2 E0YCS2_SOLHA Solanum habrochaites 2 0.7076
Methylketone synthase I E0YCS2 E0YCS2_SOLHA Solanum habrochaites 2 0.7076

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