Antrocarine A - Compound Card

Antrocarine A

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Antrocarine A

Structure
Zoomed Structure
  • Family: Plantae - Ebenaceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Triterpene
Canonical Smiles CC(C(=C)CC[C@H]([C@H]1CCC2[C@]1(C)CCC1C2C(O)[C@@H](C2=CCCC[C@]12C)O)C)C
InChI InChI=1S/C28H46O2/c1-17(2)18(3)10-11-19(4)20-12-13-21-24-22(14-16-28(20,21)6)27(5)15-8-7-9-23(27)25(29)26(24)30/h9,17,19-22,24-26,29-30H,3,7-8,10-16H2,1-2,4-6H3/t19-,20-,21?,22?,24?,25-,26?,27-,28-/m1/s1
InChIKey SSLPGGYQJSYCAP-DQKCCRMRSA-N
Formula C28H46O2
HBA 2
HBD 2
MW 414.67
Rotatable Bonds 5
TPSA 40.46
LogP 6.53
Number Rings 4
Number Aromatic Rings 0
Heavy Atom Count 30
Formal Charge 0
Fraction CSP3 0.86
Exact Mass 414.35
Number of Lipinski Rule Violations 1
# Species Family Kingdom NCBI Taxonomy ID
1 Antrocaryon klaineanum Anacardiaceae Plantae 289695
2 Diospyros conocarpa Ebenaceae Plantae 2708806

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]
  • Fouokeng Y, Akak CM, et al. (2017). The structure of antrocarine E, an ergostane isolated from Antrocaryon klaineanum Pierre (Anacardiaceae).. Fitoterapia,2017, 117, 61-64. [View] [PubMed]
Pubchem: 145999689

No compound-protein relationship available.

Structure

SMILES: C1CCC(C12)CCC3C2CCC=4C3CCCC4

Level: 0

Mol. Weight: 414.67 g/mol

Antitrypanosomal

Absorption

Caco-2 (logPapp)
-4.83
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.45
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-3.08

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.46
Plasma Protein Binding
74.41
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
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
9.75
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.73
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
1.08
Liver Injury II
Safe
hERG Blockers
Toxic
Daphnia Maga
5.76
Micronucleos
Safe
NR-AhR
Safe
NR-AR
Toxic
NR-AR-LBD
Safe
NR-Aromatase
Safe
NR-ER
Safe
NR-ER-LBD
Safe
NR-GR
Toxic
NR-PPAR-gamma
Safe
NR-TR
Safe
T. Pyriformis
-29.72
Rat (Acute)
2.59
Rat (Chronic Oral)
2.04
Fathead Minnow
4.08
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
395.44
Hydration Free Energy
-3.55
Log(D) at pH=7.4
5.73
Log(P)
7.16
Log S
-6.2
Log(Vapor Pressure)
-7.96
Melting Point
147.93
pKa Acid
11.57
pKa Basic
7.42
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8890
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8890
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 3 0.8804
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 3 0.8804
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.8570
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.8570
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8256
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8256
Enoyl-[acyl-carrier-protein] reductase [NADH] P9WGR1 INHA_MYCTU Mycobacterium tuberculosis 3 0.8037
Enoyl-[acyl-carrier-protein] reductase [NADH] P9WGR1 INHA_MYCTU Mycobacterium tuberculosis 3 0.8037
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7934
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7934
Integrin alpha-L P20701 ITAL_HUMAN Homo sapiens 3 0.7927
Integrin alpha-L P20701 ITAL_HUMAN Homo sapiens 3 0.7927
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7918
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7918
3-ketosteroid dehydrogenase Q9RA02 Q9RA02_RHOER Rhodococcus erythropolis 2 0.7831
3-ketosteroid dehydrogenase Q9RA02 Q9RA02_RHOER Rhodococcus erythropolis 2 0.7831
Nuclear receptor ROR-alpha P35398 RORA_HUMAN Homo sapiens 4 0.7680
Nuclear receptor ROR-alpha P35398 RORA_HUMAN Homo sapiens 4 0.7680
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 3 0.7666
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 3 0.7666
Methylketone synthase I E0YCS2 E0YCS2_SOLHA Solanum habrochaites 2 0.7654
Methylketone synthase I E0YCS2 E0YCS2_SOLHA Solanum habrochaites 2 0.7654
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7611
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7611
Cholesterol side-chain cleavage enzyme, mitochondrial P00189 CP11A_BOVIN Bos taurus 4 0.7587
Cholesterol side-chain cleavage enzyme, mitochondrial P00189 CP11A_BOVIN Bos taurus 4 0.7587
Steroid C26-monooxygenase P9WPP1 CP125_MYCTU Mycobacterium tuberculosis 3 0.7479
Steroid C26-monooxygenase P9WPP1 CP125_MYCTU Mycobacterium tuberculosis 3 0.7479
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 3 0.7449
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 3 0.7449
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7431
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7431
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7339
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7339
Sodium-dependent dopamine transporter Q7K4Y6 DAT_DROME Drosophila melanogaster 2 0.7323
Sodium-dependent dopamine transporter Q7K4Y6 DAT_DROME Drosophila melanogaster 2 0.7323
11-beta-hydroxysteroid dehydrogenase 1 P50172 DHI1_MOUSE Mus musculus 3 0.7206
11-beta-hydroxysteroid dehydrogenase 1 P50172 DHI1_MOUSE Mus musculus 3 0.7206
Cellular retinol-binding protein type II Q8UVG6 Q8UVG6_DANRE Danio rerio 3 0.7114
Cellular retinol-binding protein type II Q8UVG6 Q8UVG6_DANRE Danio rerio 3 0.7114
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7112
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7112
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7055
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7055
Vitamin D-binding protein P02774 VTDB_HUMAN Homo sapiens 2 0.7054
Vitamin D-binding protein P02774 VTDB_HUMAN Homo sapiens 2 0.7054
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 3 0.7019
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 3 0.7019

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