6alpha-methoxy-4,24(28)-ergostadien-7alpha-ol - Compound Card

6alpha-methoxy-4,24(28)-ergostadien-7alpha-ol

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6alpha-methoxy-4,24(28)-ergostadien-7alpha-ol

Structure
Zoomed Structure
  • Family: Plantae - Anacardiaceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Triterpene
Canonical Smiles CO[C@H]1[C@@H](O)C2C3CCC([C@@]3(C)CCC2[C@@]2(C1=CCCC2)C)[C@@H](CCC(=C)C(C)C)C
InChI InChI=1S/C29H48O2/c1-18(2)19(3)11-12-20(4)21-13-14-22-25-23(15-17-29(21,22)6)28(5)16-9-8-10-24(28)27(31-7)26(25)30/h10,18,20-23,25-27,30H,3,8-9,11-17H2,1-2,4-7H3/t20-,21?,22?,23?,25?,26+,27-,28-,29-/m1/s1
InChIKey WXPRQGPGQDZXBG-ZPLNLATJSA-N
Formula C29H48O2
HBA 2
HBD 1
MW 428.7
Rotatable Bonds 6
TPSA 29.46
LogP 7.18
Number Rings 4
Number Aromatic Rings 0
Heavy Atom Count 31
Formal Charge 0
Fraction CSP3 0.86
Exact Mass 428.37
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]
Pubchem: 122390693

No compound-protein relationship available.

Structure

SMILES: C1CCC(C12)CCC3C2CCC=4C3CCCC4

Level: 0

Mol. Weight: 428.7 g/mol

Anti-plasmodial

Absorption

Caco-2 (logPapp)
-4.83
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.450
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.97

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.610
Plasma Protein Binding
74.26
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
8.940
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
1.630
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.690
Liver Injury II
Safe
hERG Blockers
Toxic
Daphnia Maga
6.850
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
-50.230
Rat (Acute)
2.610
Rat (Chronic Oral)
1.640
Fathead Minnow
4.380
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
421.240
Hydration Free Energy
-3.480
Log(D) at pH=7.4
5.450
Log(P)
7.8
Log S
-6.67
Log(Vapor Pressure)
-7.43
Melting Point
122.51
pKa Acid
12.31
pKa Basic
7.22
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 3 0.9524
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 3 0.9524
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8549
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8549
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8512
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8512
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8306
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8306
Beta-lactoglobulin P02754 LACB_BOVIN Bos taurus 3 0.8282
Beta-lactoglobulin P02754 LACB_BOVIN Bos taurus 3 0.8282
Vitamin D(3) 25-hydroxylase C4B644 CPVDH_PSEAH Pseudonocardia autotrophica 3 0.8218
Vitamin D(3) 25-hydroxylase C4B644 CPVDH_PSEAH Pseudonocardia autotrophica 3 0.8218
Integrin alpha-L P20701 ITAL_HUMAN Homo sapiens 3 0.8183
Integrin alpha-L P20701 ITAL_HUMAN Homo sapiens 3 0.8183
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8147
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8147
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 3 0.7845
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 3 0.7845
Protein BRASSINOSTEROID INSENSITIVE 1 O22476 BRI1_ARATH Arabidopsis thaliana 3 0.7772
Protein BRASSINOSTEROID INSENSITIVE 1 O22476 BRI1_ARATH Arabidopsis thaliana 3 0.7772
Retinol-binding protein 1 P02696 RET1_RAT Rattus norvegicus 3 0.7768
Retinol-binding protein 1 P02696 RET1_RAT Rattus norvegicus 3 0.7768
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7605
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7605
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7602
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7602
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7550
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7550
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7497
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7497
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 3 0.7472
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 3 0.7472
Methionine aminopeptidase 1 P53582 MAP11_HUMAN Homo sapiens 2 0.7461
Methionine aminopeptidase 1 P53582 MAP11_HUMAN Homo sapiens 2 0.7461
Retinol dehydratase Q26490 Q26490_SPOFR Spodoptera frugiperda 3 0.7439
Retinol dehydratase Q26490 Q26490_SPOFR Spodoptera frugiperda 3 0.7439
Beta-lactoglobulin P02754 LACB_BOVIN Bos taurus 3 0.7391
Beta-lactoglobulin P02754 LACB_BOVIN Bos taurus 3 0.7391
Vitamin D3 receptor P13053 VDR_RAT Rattus norvegicus 3 0.7351
Vitamin D3 receptor P13053 VDR_RAT Rattus norvegicus 3 0.7351
Protein BRASSINOSTEROID INSENSITIVE 1 O22476 BRI1_ARATH Arabidopsis thaliana 3 0.7307
Protein BRASSINOSTEROID INSENSITIVE 1 O22476 BRI1_ARATH Arabidopsis thaliana 3 0.7307
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 3 0.7303
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 3 0.7303
Sodium-dependent dopamine transporter Q7K4Y6 DAT_DROME Drosophila melanogaster 2 0.7301
Sodium-dependent dopamine transporter Q7K4Y6 DAT_DROME Drosophila melanogaster 2 0.7301
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7286
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7286
Cholesterol side-chain cleavage enzyme, mitochondrial P00189 CP11A_BOVIN Bos taurus 4 0.7261
Cholesterol side-chain cleavage enzyme, mitochondrial P00189 CP11A_BOVIN Bos taurus 4 0.7261
Japanin M1MR49 M1MR49_RHIAP Rhipicephalus appendiculatus 3 0.7136
Japanin M1MR49 M1MR49_RHIAP Rhipicephalus appendiculatus 3 0.7136
Nuclear receptor ROR-alpha P35398 RORA_HUMAN Homo sapiens 4 0.7130
Nuclear receptor ROR-alpha P35398 RORA_HUMAN Homo sapiens 4 0.7130
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 3 0.7023
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 3 0.7023
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7006
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7006

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