3beta,22(S)-dihydroxycycloart-24E-en-26-oic acid - Compound Card

3beta,22(S)-dihydroxycycloart-24E-en-26-oic acid

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3beta,22(S)-dihydroxycycloart-24E-en-26-oic acid

Structure
Zoomed Structure
  • Family: Plantae - Anacardiaceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Triterpene
Canonical Smiles O[C@H]([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](C2(C)C)O)C)C)C/C=C(/C(=O)O)\C
InChI InChI=1S/C30H48O4/c1-18(25(33)34)7-8-21(31)19(2)20-11-13-28(6)23-10-9-22-26(3,4)24(32)12-14-29(22)17-30(23,29)16-15-27(20,28)5/h7,19-24,31-32H,8-17H2,1-6H3,(H,33,34)/b18-7+/t19-,20+,21-,22-,23-,24-,27+,28-,29+,30-/m0/s1
InChIKey WCKMOTWOWWZGCU-QGHBHSBYSA-N
Formula C30H48O4
HBA 3
HBD 3
MW 472.71
Rotatable Bonds 5
TPSA 77.76
LogP 6.2
Number Rings 5
Number Aromatic Rings 0
Heavy Atom Count 34
Formal Charge 0
Fraction CSP3 0.9
Exact Mass 472.36
Number of Lipinski Rule Violations 1
# Species Family Kingdom NCBI Taxonomy ID
1 Antrocaryon klaineanum Anacardiaceae Plantae 289695

Showing of synonyms

  • Fouokeng Y, Feusso HMF, et al. (2019). In vitro antimalarial, antitrypanosomal and HIV-1 integrase inhibitory activities of two Cameroonian medicinal plants: Antrocaryon klaineanum (Anacardiaceae) and Diospyros conocarpa (Ebenaceae).. South African Journal of Botany, 2019, 122, 510-517. [View]

No compound-protein relationship available.

Structure

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

Level: 0

Mol. Weight: 472.71 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-5.31
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.96
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-3.25

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.74
Plasma Protein Binding
101.93
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
Non-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
Inhibitor
OATP1B3
Inhibitor

Excretion

Clearance
2.88
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-1.55
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
1.0
Liver Injury II
Toxic
hERG Blockers
Toxic
Daphnia Maga
3.49
Micronucleos
Safe
NR-AhR
Safe
NR-AR
Safe
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
-205.2
Rat (Acute)
2.35
Rat (Chronic Oral)
1.96
Fathead Minnow
3.75
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
464.54
Hydration Free Energy
-2.3
Log(D) at pH=7.4
4.28
Log(P)
6.03
Log S
-6.0
Log(Vapor Pressure)
-10.56
Melting Point
264.82
pKa Acid
4.75
pKa Basic
7.21
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 0.8388
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8388
Aldo-keto reductase family 1 member C1 Q04828 AK1C1_HUMAN Homo sapiens 3 0.8363
Aldo-keto reductase family 1 member C1 Q04828 AK1C1_HUMAN Homo sapiens 3 0.8363
3-alpha-(or 20-beta)-hydroxysteroid dehydrogenase P19992 HSD_STREX Streptomyces exfoliatus 3 0.7949
3-alpha-(or 20-beta)-hydroxysteroid dehydrogenase P19992 HSD_STREX Streptomyces exfoliatus 3 0.7949
4,5:9,10-diseco-3-hydroxy-5,9,17-trioxoandrosta-1(10),2-diene-4-oate hydrolase P9WNH5 HSAD_MYCTU Mycobacterium tuberculosis 3 0.7924
4,5:9,10-diseco-3-hydroxy-5,9,17-trioxoandrosta-1(10),2-diene-4-oate hydrolase P9WNH5 HSAD_MYCTU Mycobacterium tuberculosis 3 0.7924
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7923
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7923
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7884
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7884
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 3 0.7875
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 3 0.7875
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 3 0.7816
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 3 0.7816
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7740
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7740
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7636
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7636
Retinol-binding protein 1 P09455 RET1_HUMAN Homo sapiens 4 0.7575
Retinol-binding protein 1 P09455 RET1_HUMAN Homo sapiens 4 0.7575
N-alpha-acetyltransferase 50 Q9GZZ1 NAA50_HUMAN Homo sapiens 3 0.7460
N-alpha-acetyltransferase 50 Q9GZZ1 NAA50_HUMAN Homo sapiens 3 0.7460
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 3 0.7457
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 3 0.7457
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7184
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7184

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