(20S)-3beta-acetoxy-12beta,16beta,25-tetrahydroxydammar-23-ene - Compound Card

(20S)-3beta-acetoxy-12beta,16beta,25-tetrahydroxydammar-23-ene

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(20S)-3beta-acetoxy-12beta,16beta,25-tetrahydroxydammar-23-ene

Structure
Zoomed Structure
  • Family: Plantae - Burseraceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Dammarane Triterpene
Canonical Smiles CC(=O)O[C@@]1(O)CC[C@]2(C(C1(C)C)CC[C@@H]1[C@@H]2C[C@@H](O)C2[C@]1(C)C[C@@H]([C@@H]2[C@H](C/C=C/C(O)(C)C)C)O)C
InChI InChI=1S/C31H52O6/c1-18(10-9-13-27(3,4)35)25-23(34)17-30(8)20-11-12-24-28(5,6)31(36,37-19(2)32)15-14-29(24,7)21(20)16-22(33)26(25)30/h9,13,18,20-26,33-36H,10-12,14-17H2,1-8H3/b13-9+/t18-,20+,21-,22+,23-,24?,25-,26?,29+,30+,31-/m0/s1
InChIKey PXTJUJYHGKKSCW-LRMRNDJNSA-N
Formula C31H52O6
HBA 6
HBD 4
MW 520.75
Rotatable Bonds 5
TPSA 107.22
LogP 4.83
Number Rings 4
Number Aromatic Rings 0
Heavy Atom Count 37
Formal Charge 0
Fraction CSP3 0.9
Exact Mass 520.38
Number of Lipinski Rule Violations 1
# Species Family Kingdom NCBI Taxonomy ID
1 Commiphora confusa Burseraceae Plantae 43868

Showing of synonyms

  • Manguro LO, Ugi I, et al. (2003). Dammarane triterpenes of Commiphora confusa resin. Chemical and Pharmaceutical Bulletin,2003,51(5),483-486. [View] [PubMed]

No compound-protein relationship available.

Structure

SMILES: C1CCC(C12)CCC3C2CCC4C3CCCC4

Level: 0

Mol. Weight: 520.75 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.97
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.9
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
-2.46

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.02
Plasma Protein Binding
86.28
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
3.55
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.78
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.33
Liver Injury II
Safe
hERG Blockers
Toxic
Daphnia Maga
6.6
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
-333.18
Rat (Acute)
4.58
Rat (Chronic Oral)
2.02
Fathead Minnow
4.02
Respiratory Disease
Toxic
Skin Sensitisation
Safe
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Safe

General Properties

Boiling Point
478.54
Hydration Free Energy
-3.03
Log(D) at pH=7.4
4.16
Log(P)
4.61
Log S
-4.96
Log(Vapor Pressure)
-8.86
Melting Point
200.63
pKa Acid
7.89
pKa Basic
6.68
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 0.9080
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.9080
Vitamin D(3) 25-hydroxylase C4B644 CPVDH_PSEAH Pseudonocardia autotrophica 3 0.8601
Vitamin D(3) 25-hydroxylase C4B644 CPVDH_PSEAH Pseudonocardia autotrophica 3 0.8601
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8433
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8433
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 3 0.8408
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 3 0.8408
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8331
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8331
Prolyl tripeptidyl peptidase Q7MUW6 PTP_PORGI Porphyromonas gingivalis 3 0.8194
Prolyl tripeptidyl peptidase Q7MUW6 PTP_PORGI Porphyromonas gingivalis 3 0.8194
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8132
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8132
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.8125
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.8125
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 3 0.7984
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 3 0.7984
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7932
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7932
3-alpha-hydroxysteroid dehydrogenase P23457 DIDH_RAT Rattus norvegicus 3 0.7782
3-alpha-hydroxysteroid dehydrogenase P23457 DIDH_RAT Rattus norvegicus 3 0.7782
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.7745
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.7745
Gastrotropin Q6IMW5 Q6IMW5_DANRE Danio rerio 3 0.7631
Gastrotropin Q6IMW5 Q6IMW5_DANRE Danio rerio 3 0.7631
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7551
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7551
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7531
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7531
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7491
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7491
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7449
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7449
Gastrotropin P51161 FABP6_HUMAN Homo sapiens 3 0.7214
Gastrotropin P51161 FABP6_HUMAN Homo sapiens 3 0.7214
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7211
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7211
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.7146
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.7146
N-alpha-acetyltransferase 50 Q9GZZ1 NAA50_HUMAN Homo sapiens 3 0.7140
N-alpha-acetyltransferase 50 Q9GZZ1 NAA50_HUMAN Homo sapiens 3 0.7140
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7075
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7075
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 4 0.7036
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 4 0.7036
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7000
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7000

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