3-beta-acetate-12,20(29)-lupadien-28-oic acid - Compound Card

3-beta-acetate-12,20(29)-lupadien-28-oic acid

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3-beta-acetate-12,20(29)-lupadien-28-oic acid

Structure
Zoomed Structure
  • Family: Plantae - Myrtaceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Pentacyclic Triterpenoid
Canonical Smiles CC(=C)[C@@H]1CC[C@]2([C@H]1[C@H]1C=C[C@H]3[C@@]([C@]1(C)CC2)(C)CC[C@@H]1[C@]3(C)CC[C@@H](C1(C)C)C(=O)C)C(=O)O
InChI InChI=1S/C32H48O3/c1-19(2)21-11-16-32(27(34)35)18-17-30(7)23(26(21)32)9-10-25-29(6)14-12-22(20(3)33)28(4,5)24(29)13-15-31(25,30)8/h9-10,21-26H,1,11-18H2,2-8H3,(H,34,35)/t21-,22+,23+,24-,25+,26+,29-,30+,31+,32-/m0/s1
InChIKey BOQRQZGCBZIJHL-WEQCPXDJSA-N
Formula C32H48O3
HBA 2
HBD 1
MW 480.73
Rotatable Bonds 3
TPSA 54.37
LogP 7.71
Number Rings 5
Number Aromatic Rings 0
Heavy Atom Count 35
Formal Charge 0
Fraction CSP3 0.81
Exact Mass 480.36
Number of Lipinski Rule Violations 1
# Species Family Kingdom NCBI Taxonomy ID
1 Eucalyptus cladocalyx Myrtaceae Plantae 452569

Showing of synonyms

  • Benyahia S, Benayache S, et al. (2005). Cladocalol, a pentacyclic 28-nor-triterpene from Eucalyptus cladocalyxwith cytotoxic activity. Phytochemistry, 2005, 66(6), 627-32. [View] [PubMed]

No compound-protein relationship available.

Structure

SMILES: C1CCC(C12)CCC3C2C=CC4C3CCC5C4CCCC5

Level: 0

Mol. Weight: 480.73 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-5.38
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.75
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.36

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
2.5
Plasma Protein Binding
97.73
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
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
Inhibitor
OATP1B3
Inhibitor

Excretion

Clearance
2.29
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.13
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
2.1
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
3.31
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
-252.17
Rat (Acute)
2.35
Rat (Chronic Oral)
1.94
Fathead Minnow
3.96
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
488.25
Hydration Free Energy
-2.93
Log(D) at pH=7.4
5.42
Log(P)
6.75
Log S
-6.59
Log(Vapor Pressure)
-9.67
Melting Point
250.87
pKa Acid
6.52
pKa Basic
7.37
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.9237
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8534
Deacetoxycephalosporin C synthase P18548 CEFE_STRCL Streptomyces clavuligerus 3 0.8340
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8131
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8019
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7956
Abscisic acid receptor PYL3 Q9SSM7 PYL3_ARATH Arabidopsis thaliana 3 0.7741
Avidin P02701 AVID_CHICK Gallus gallus 2 0.7181
Corticosteroid-binding globulin P31211 CBG_RAT Rattus norvegicus 3 0.7132
Abscisic acid receptor PYL2 O80992 PYL2_ARATH Arabidopsis thaliana 3 0.7096
Cholesterol side-chain cleavage enzyme, mitochondrial P00189 CP11A_BOVIN Bos taurus 4 0.7052
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 2 0.7034

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