3beta-acetoxy-16beta,20(R)-dihydroxydammar-24-ene - Compound Card

3beta-acetoxy-16beta,20(R)-dihydroxydammar-24-ene

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3beta-acetoxy-16beta,20(R)-dihydroxydammar-24-ene

Structure
Zoomed Structure
  • Family: Plantae - Burseraceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Triterpenoid
Canonical Smiles CC(=CCC[C@]([C@H]1[C@@H](O)C[C@]2(C1CC[C@H]1[C@H]2CCC2[C@]1(C)CC[C@@H](C2(C)C)OC(=O)C)C)(O)C)C
InChI InChI=1S/C31H52O4/c1-19(2)10-9-16-31(8,34)27-23-12-11-21-22(30(23,7)18-24(27)33)13-14-25-28(4,5)26(35-20(3)32)15-17-29(21,25)6/h10,21-27,33-34H,9,11-18H2,1-8H3/t21-,22+,23?,24-,25?,26-,27+,29+,30+,31+/m0/s1
InChIKey BFFWFQRNBOXUAS-IQDQOMQOSA-N
Formula C31H52O4
HBA 4
HBD 2
MW 488.75
Rotatable Bonds 5
TPSA 66.76
LogP 6.68
Number Rings 4
Number Aromatic Rings 0
Heavy Atom Count 35
Formal Charge 0
Fraction CSP3 0.9
Exact Mass 488.39
Number of Lipinski Rule Violations 1
# Species Family Kingdom NCBI Taxonomy ID
1 Commiphora kua Burseraceae Plantae 246356
2 Boswellia species Burseraceae Plantae 173701

Showing of synonyms

  • Manguro LO, Ugi I, et al. (2003). Further bisabolenes and dammarane triterpenes of Commiphora kua resin.. Chemical and Pharmaceutical Bulletin,2003,51(5),479-482. [View] [PubMed]
  • Melese A, Dagne E. (2007). Phytochemical investigation of the resins of Boswellia species collected from Kebtele area in Agew-Awi (Gojjam). M.Sc. Thesis, Addis Ababa University, Ethiopia, 2007. [View] [PubMed]

No compound-protein relationship available.

Structure

SMILES: C1CCC(C12)CCC3C2CCC4C3CCCC4

Level: 0

Mol. Weight: 488.75 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.87
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
-2.47

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.43
Plasma Protein Binding
86.17
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
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
Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
4.08
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.36
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.7
Liver Injury II
Toxic
hERG Blockers
Toxic
Daphnia Maga
6.56
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
-173.36
Rat (Acute)
2.31
Rat (Chronic Oral)
1.75
Fathead Minnow
3.93
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
477.37
Hydration Free Energy
-2.85
Log(D) at pH=7.4
5.63
Log(P)
6.79
Log S
-6.46
Log(Vapor Pressure)
-8.59
Melting Point
180.35
pKa Acid
10.87
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 C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8537
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8537
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.8456
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.8456
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 3 0.8361
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 3 0.8361
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7908
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7908
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.7596
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.7596
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7383
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7383
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.7272
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.7272
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7212
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7212
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7167
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7167
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 2 0.7052
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 2 0.7052

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