3,4-seco-mansumbinoic acid - Compound Card

3,4-seco-mansumbinoic acid

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3,4-seco-mansumbinoic acid

Structure
Zoomed Structure
  • Family: Burseraceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Octanordammarane
Canonical Smiles OC(=O)CC[C@@]1(C)[C@@H](CC[C@@]2([C@H]1CC[C@@H]1[C@@]2(C)CC=C1)C)C(=C)C
InChI InChI=1S/C22H34O2/c1-15(2)17-10-14-22(5)18(20(17,3)13-11-19(23)24)9-8-16-7-6-12-21(16,22)4/h6-7,16-18H,1,8-14H2,2-5H3,(H,23,24)/t16-,17+,18+,20+,21-,22-/m1/s1
InChIKey JHGHHJNAAWXVMF-XQAJHESWSA-N
Formula C22H34O2
HBA 1
HBD 1
MW 330.51
Rotatable Bonds 4
TPSA 37.3
LogP 5.84
Number Rings 3
Number Aromatic Rings 0
Heavy Atom Count 24
Formal Charge 0
Fraction CSP3 0.77
Exact Mass 330.26
Number of Lipinski Rule Violations 1
# Species Family Kingdom NCBI Taxonomy ID
1 Commiphora molmol Burseraceae Plantae 318982

Showing of synonyms

  • Rahman MM, Garvey M, et al. (2008). Antibacterial terpenes from the oleo-resin of Commiphora molmol (Engl.). Phytotherapy Research,2008,22(10),1356-1360. [View] [PubMed]
Pubchem: 163037638
Nmrshiftdb2: 60115441

No compound-protein relationship available.

Structure

SMILES: C1=CCC(C12)C3C(CC2)CCCC3

Level: 0

Mol. Weight: 176.3 g/mol

Antibacterial

Absorption

Caco-2 (logPapp)
-4.66
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.7
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.68

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.24
Plasma Protein Binding
87.68
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
Non-Substrate
CYP 2C9 Inhibitor
Non-Inhibitor
CYP 2C9 Substrate
Substrate
CYP 2D6 Inhibitor
Non-Inhibitor
CYP 2D6 Substrate
Non-Substrate
CYP 3A4 Inhibitor
Non-Inhibitor
CYP 3A4 Substrate
Substrate
OATP1B1
Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
1.65
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.59
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
0.85
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
3.28
Micronucleos
Safe
NR-AhR
Safe
NR-AR
Safe
NR-AR-LBD
Safe
NR-Aromatase
Safe
NR-ER
Safe
NR-ER-LBD
Safe
NR-GR
Safe
NR-PPAR-gamma
Safe
NR-TR
Safe
T. Pyriformis
-1.38
Rat (Acute)
2.2
Rat (Chronic Oral)
1.26
Fathead Minnow
3.9
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
379.09
Hydration Free Energy
-3.25
Log(D) at pH=7.4
3.13
Log(P)
5.7
Log S
-5.5
Log(Vapor Pressure)
-7.21
Melting Point
160.38
pKa Acid
6.38
pKa Basic
7.65
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.8042
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.8042
Beta-lactoglobulin P02754 LACB_BOVIN Bos taurus 3 0.7882
Beta-lactoglobulin P02754 LACB_BOVIN Bos taurus 3 0.7882
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7870
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7870
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7842
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7842
Retinol-binding protein 2 P50120 RET2_HUMAN Homo sapiens 3 0.7712
Retinol-binding protein 2 P50120 RET2_HUMAN Homo sapiens 3 0.7712
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 2 0.7654
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 2 0.7654
Retinol-binding protein 2 P50120 RET2_HUMAN Homo sapiens 3 0.7648
Retinol-binding protein 2 P50120 RET2_HUMAN Homo sapiens 3 0.7648
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 3 0.7508
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 3 0.7508
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7398
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7398
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7392
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7392
Retinol dehydratase Q26490 Q26490_SPOFR Spodoptera frugiperda 3 0.7388
Retinol dehydratase Q26490 Q26490_SPOFR Spodoptera frugiperda 3 0.7388
Retinol-binding protein 1 P09455 RET1_HUMAN Homo sapiens 3 0.7345
Retinol-binding protein 1 P09455 RET1_HUMAN Homo sapiens 3 0.7345
Lanosterol synthase P48449 ERG7_HUMAN Homo sapiens 3 0.7292
Lanosterol synthase P48449 ERG7_HUMAN Homo sapiens 3 0.7292
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7281
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7281
Streptavidin P22629 SAV_STRAV Streptomyces avidinii 2 0.7257
Streptavidin P22629 SAV_STRAV Streptomyces avidinii 2 0.7257
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.7248
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.7248
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7216
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7216
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7184
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7184
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7181
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7181
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 2 0.7169
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 2 0.7169
Bacteriorhodopsin P02945 BACR_HALSA Halobacterium salinarum 3 0.7113
Bacteriorhodopsin P02945 BACR_HALSA Halobacterium salinarum 3 0.7113
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 2 0.7047
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 2 0.7047

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