4,24(28)-ergostadiene-6alpla,7alpha-diol - Compound Card

4,24(28)-ergostadiene-6alpla,7alpha-diol

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4,24(28)-ergostadiene-6alpla,7alpha-diol

Structure
Zoomed Structure
  • Family: Anacardiaceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Triterpene
Canonical Smiles CC(C(=C)CC[C@H](C1CCC2[C@]1(C)CCC1C2[C@H](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-BVGOMKNWSA-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

Showing of synonyms

  • DouanlaPD, Tabopda TK, et al. (2015). Antrocarines A-F, antiplasmodial ergostane steroids from the stem bark of Antrocaryon klaineanum.. Phytochemistry,2015, 117, 521-526. [View] [PubMed]

No compound-protein relationship available.

Structure

SMILES: C1CCC(C12)CCC3C2CCC=4C3CCCC4

Level: 0

Mol. Weight: 230.39 g/mol

Anti-plasmodial

Absorption

Caco-2 (logPapp)
-4.84
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.48
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.89

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.51
Plasma Protein Binding
73.5
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
8.53
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
1.11
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.71
Liver Injury II
Safe
hERG Blockers
Toxic
Daphnia Maga
5.64
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
-29.85
Rat (Acute)
2.5
Rat (Chronic Oral)
1.8
Fathead Minnow
4.34
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
430.42
Hydration Free Energy
-4.26
Log(D) at pH=7.4
5.49
Log(P)
7.14
Log S
-6.12
Log(Vapor Pressure)
-8.1
Melting Point
146.17
pKa Acid
11.84
pKa Basic
7.5
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 3 0.9458
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 3 0.9458
Enoyl-[acyl-carrier-protein] reductase [NADH] P9WGR1 INHA_MYCTU Mycobacterium tuberculosis 3 0.8712
Enoyl-[acyl-carrier-protein] reductase [NADH] P9WGR1 INHA_MYCTU Mycobacterium tuberculosis 3 0.8712
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8310
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8310
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8223
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8223
Beta-lactoglobulin P02754 LACB_BOVIN Bos taurus 3 0.8147
Beta-lactoglobulin P02754 LACB_BOVIN Bos taurus 3 0.8147
Protein BRASSINOSTEROID INSENSITIVE 1 O22476 BRI1_ARATH Arabidopsis thaliana 3 0.8073
Protein BRASSINOSTEROID INSENSITIVE 1 O22476 BRI1_ARATH Arabidopsis thaliana 3 0.8073
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8053
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8053
Integrin alpha-L P20701 ITAL_HUMAN Homo sapiens 3 0.7960
Integrin alpha-L P20701 ITAL_HUMAN Homo sapiens 3 0.7960
Lanosterol 14-alpha-demethylase Q385E8 Q385E8_TRYB2 Trypanosoma brucei brucei 4 0.7938
Lanosterol 14-alpha-demethylase Q385E8 Q385E8_TRYB2 Trypanosoma brucei brucei 4 0.7938
Retinol-binding protein 1 P02696 RET1_RAT Rattus norvegicus 3 0.7712
Retinol-binding protein 1 P02696 RET1_RAT Rattus norvegicus 3 0.7712
Methylketone synthase I E0YCS2 E0YCS2_SOLHA Solanum habrochaites 2 0.7678
Methylketone synthase I E0YCS2 E0YCS2_SOLHA Solanum habrochaites 2 0.7678
Cholesterol side-chain cleavage enzyme, mitochondrial P00189 CP11A_BOVIN Bos taurus 4 0.7673
Cholesterol side-chain cleavage enzyme, mitochondrial P00189 CP11A_BOVIN Bos taurus 4 0.7673
Vitamin D(3) 25-hydroxylase C4B644 CPVDH_PSEAH Pseudonocardia autotrophica 3 0.7661
Vitamin D(3) 25-hydroxylase C4B644 CPVDH_PSEAH Pseudonocardia autotrophica 3 0.7661
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7645
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7645
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7636
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7636
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7563
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7563
Protein BRASSINOSTEROID INSENSITIVE 1 O22476 BRI1_ARATH Arabidopsis thaliana 3 0.7545
Protein BRASSINOSTEROID INSENSITIVE 1 O22476 BRI1_ARATH Arabidopsis thaliana 3 0.7545
Protein BRASSINOSTEROID INSENSITIVE 1 O22476 BRI1_ARATH Arabidopsis thaliana 3 0.7505
Protein BRASSINOSTEROID INSENSITIVE 1 O22476 BRI1_ARATH Arabidopsis thaliana 3 0.7505
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7307
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7307
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.7186
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.7186
Sodium-dependent dopamine transporter Q7K4Y6 DAT_DROME Drosophila melanogaster 2 0.7147
Sodium-dependent dopamine transporter Q7K4Y6 DAT_DROME Drosophila melanogaster 2 0.7147
Nuclear receptor ROR-alpha P35398 RORA_HUMAN Homo sapiens 4 0.7133
Nuclear receptor ROR-alpha P35398 RORA_HUMAN Homo sapiens 4 0.7133
Retinol dehydratase Q26490 Q26490_SPOFR Spodoptera frugiperda 3 0.7065
Retinol dehydratase Q26490 Q26490_SPOFR Spodoptera frugiperda 3 0.7065

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