Stigmast-4,22-dien-3-one - Compound Card

Stigmast-4,22-dien-3-one

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Stigmast-4,22-dien-3-one

Structure
Zoomed Structure
  • Family: Plantae - Guttiferae
  • Kingdom: Plantae
  • Class: Steroid
    • Subclass: Phytosterol
Canonical Smiles CC[C@@H](C(C)C)/C=C/[C@H]([C@H]1CC[C@@H]2[C@]1(C)CC[C@H]1[C@H]2CCC2=CC(=O)CC[C@]12C)C
InChI InChI=1S/C29H46O/c1-7-21(19(2)3)9-8-20(4)25-12-13-26-24-11-10-22-18-23(30)14-16-28(22,5)27(24)15-17-29(25,26)6/h8-9,18-21,24-27H,7,10-17H2,1-6H3/b9-8+/t20-,21-,24+,25-,26+,27+,28+,29-/m1/s1
InChIKey MKGZDUKUQPPHFM-LPJPOILFSA-N
Formula C29H46O
HBA 1
HBD 0
MW 410.69
Rotatable Bonds 5
TPSA 17.07
LogP 8.01
Number Rings 4
Number Aromatic Rings 0
Heavy Atom Count 30
Formal Charge 0
Fraction CSP3 0.83
Exact Mass 410.35
Number of Lipinski Rule Violations 1
# Species Family Kingdom NCBI Taxonomy ID
1 Alchornea cordifolia Euphorbiaceae Plantae 316697
2 Pentadesma butyracea Guttiferae Plantae 198785

Showing of synonyms

  • Tala M, Wabo H, et al. (2013). A prenylated xanthone and antiproliferative compounds from leaves of Pentadesma butyracea. Phytochemistry Letters, 2013, 6(3), 326-330. [View]
  • Siwe-Noundou X, Musyoka TM, et al. (2019). Anti-HIV-1 integrase potency of methylgallate from Alchornea cordifolia using in vitro and in silico approaches.. Scientific reports,2019, 9(1), 4718. [View] [PubMed]
Pubchem: 6442194
Chebi: 184108
Nmrshiftdb2: 60020257

No compound-protein relationship available.

Structure

SMILES: C1CCC(C12)CCC3C2CCC=4C3CCC(=O)C4

Level: 0

Mol. Weight: 410.69 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.8
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.58
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)
2.3
Plasma Protein Binding
85.04
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Inhibitor
CYP 1A2 Inhibitor
Non-Inhibitor
CYP 1A2 Substrate
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
6.11
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
1.58
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
1.37
Liver Injury II
Safe
hERG Blockers
Toxic
Daphnia Maga
6.78
Micronucleos
Safe
NR-AhR
Safe
NR-AR
Toxic
NR-AR-LBD
Toxic
NR-Aromatase
Safe
NR-ER
Toxic
NR-ER-LBD
Safe
NR-GR
Toxic
NR-PPAR-gamma
Safe
NR-TR
Toxic
T. Pyriformis
-31.92
Rat (Acute)
2.32
Rat (Chronic Oral)
1.93
Fathead Minnow
4.23
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
441.06
Hydration Free Energy
-3.85
Log(D) at pH=7.4
6.52
Log(P)
8.16
Log S
-6.39
Log(Vapor Pressure)
-7.22
Melting Point
130.88
pKa Acid
12.36
pKa Basic
7.06
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.9494
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.9393
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.9322
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.9009
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8717
Oxysterols receptor LXR-beta P55055 NR1H2_HUMAN Homo sapiens 4 0.8348
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8333
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8299
Retinol-binding protein 1 P02696 RET1_RAT Rattus norvegicus 3 0.8237
Beta-elicitin cryptogein P15570 ELIB_PHYCR Phytophthora cryptogea 4 0.7805
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7640
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.7597
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7564
Protein BRASSINOSTEROID INSENSITIVE 1 O22476 BRI1_ARATH Arabidopsis thaliana 3 0.7552
Rhodopsin P02699 OPSD_BOVIN Bos taurus 3 0.7483
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7390
Protein BRASSINOSTEROID INSENSITIVE 1 O22476 BRI1_ARATH Arabidopsis thaliana 3 0.7355
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7306
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.7285
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 2 0.7282
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 3 0.7271
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 3 0.7256
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7248
Retinol-binding protein 1 P09455 RET1_HUMAN Homo sapiens 3 0.7239
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 2 0.7225
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 2 0.7198
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7160
Cholesterol side-chain cleavage enzyme, mitochondrial P05108 CP11A_HUMAN Homo sapiens 3 0.7160
Lanosterol 14-alpha-demethylase Q385E8 Q385E8_TRYB2 Trypanosoma brucei brucei 3 0.7110
Reaction center protein L chain P0C0Y7 RCEH_RHOSH Rhodobacter sphaeroides 2 0.7065
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7040

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