Betulinaldehyde - Compound Card

Betulinaldehyde

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Betulinaldehyde

Structure
Zoomed Structure
  • Family: Plantae - Clusiaceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Triterpene
Canonical Smiles O=C[C@@]12CC[C@H]([C@@H]2[C@@H]2[C@](CC1)(C)[C@]1(C)CC[C@@H]3[C@]([C@H]1CC2)(C)CC[C@@H](C3(C)C)O)C(=C)C
InChI InChI=1S/C30H48O2/c1-19(2)20-10-15-30(18-31)17-16-28(6)21(25(20)30)8-9-23-27(5)13-12-24(32)26(3,4)22(27)11-14-29(23,28)7/h18,20-25,32H,1,8-17H2,2-7H3/t20-,21+,22-,23+,24-,25+,27-,28+,29+,30+/m0/s1
InChIKey FELCJAPFJOPHSD-ROUWMTJPSA-N
Formula C30H48O2
HBA 2
HBD 1
MW 440.71
Rotatable Bonds 2
TPSA 37.3
LogP 7.2
Number Rings 5
Number Aromatic Rings 0
Heavy Atom Count 32
Formal Charge 0
Fraction CSP3 0.9
Exact Mass 440.37
Number of Lipinski Rule Violations 1
# Species Family Kingdom NCBI Taxonomy ID
1 Jacaranda mimosaefolia Bignoniaceae Plantae 185774
2 Melaleuca ericifolia Myrtaceae Plantae 73757
3 Garcinia livingstonei Clusiaceae Plantae 469932

Showing of synonyms

  • Abdel Bar FM, Zaghloul AM, et al. (2008). Antiproliferative triterpenes from Melaleuca ericifolia. Journal of Natural Products,2008,71(10),1787-1790. [View] [PubMed]
  • Mulholland DA, Mwangi EM, et al. (2013). Non-toxic melanin production inhibitors from Garcinia livingstonei (Clusiaceae). Journal of ethnopharmacology, 2013, 149(2), 570–575. [View]
  • Zaghloul AM, Gohar AA, et al. (2011). Phenylpropanoids from the stem bark of Jacaranda mimosaefolia. Natural Product Research,2011,25(1),68-76. [View] [PubMed]
Pubchem: 99615
Chebi: 177424
Nmrshiftdb2: 70127742

No compound-protein relationship available.

Structure

SMILES: C1CCC(C12)CCC3C2CCC4C3CCC5C4CCCC5

Level: 0

Mol. Weight: 440.71 g/mol

Antiproliferative

Absorption

Caco-2 (logPapp)
-4.91
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.39
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.46

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.33
Plasma Protein Binding
83.92
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
Non-Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
10.67
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.5
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
1.32
Liver Injury II
Safe
hERG Blockers
Toxic
Daphnia Maga
6.47
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
-77.61
Rat (Acute)
3.1
Rat (Chronic Oral)
1.38
Fathead Minnow
3.92
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
431.9
Hydration Free Energy
-2.67
Log(D) at pH=7.4
6.88
Log(P)
7.49
Log S
-6.61
Log(Vapor Pressure)
-8.66
Melting Point
211.03
pKa Acid
11.3
pKa Basic
7.17
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 0.8403
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8403
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8375
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8375
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7611
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7611
3-alpha-hydroxysteroid dehydrogenase P23457 DIDH_RAT Rattus norvegicus 3 0.7524
3-alpha-hydroxysteroid dehydrogenase P23457 DIDH_RAT Rattus norvegicus 3 0.7524
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7343
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7343
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7269
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7269
Abscisic acid receptor PYL2 O80992 PYL2_ARATH Arabidopsis thaliana 2 0.7198
Abscisic acid receptor PYL2 O80992 PYL2_ARATH Arabidopsis thaliana 2 0.7198
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7050
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7050

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