Select a section from the left sidebar
Shikimic acid
- Family: Plantae - Hypericaceae
- Kingdom: Plantae
-
Class: Terpenoid
- Subclass: Monoterpene
| Canonical Smiles | O[C@@H]1CC(=C[C@H]([C@H]1O)O)C(=O)O |
|---|---|
| InChI | InChI=1S/C7H10O5/c8-4-1-3(7(11)12)2-5(9)6(4)10/h1,4-6,8-10H,2H2,(H,11,12)/t4-,5-,6-/m1/s1 |
| InChIKey | JXOHGGNKMLTUBP-HSUXUTPPSA-N |
| Formula | C7H10O5 |
| HBA | 4 |
| HBD | 4 |
| MW | 174.15 |
| Rotatable Bonds | 1 |
| TPSA | 97.99 |
| LogP | -1.52 |
| Number Rings | 1 |
| Number Aromatic Rings | 0 |
| Heavy Atom Count | 12 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.57 |
| Exact Mass | 174.05 |
| Number of Lipinski Rule Violations | 0 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Hypericum quartinianum | Hypericaceae | Plantae | 1137015 |
Showing of synonyms
Shikimic acid
138-59-0
L-Shikimic acid
(3R,4S,5R)-3,4,5-TRIHYDROXYCYCLOHEX-1-ENE-1-CARBOXYLIC ACID
1-cyclohexene-1-carboxylic acid, 3,4,5-trihydroxy-, (3R,4S,5R)-
(3R,4S,5R)-3,4,5-Trihydroxycyclohex-1-enecarboxylic acid
(3R,4S,5R)-3,4,5-trihydroxycyclohexene-1-carboxylic acid
CCRIS 7681
HSDB 3537
3alpha,4alpha,5beta-Trihydroxy-1-cyclohexene-1-carboxylic acid
Bracken fern toxic component
Shicimic Acid
EINECS 205-334-2
29MS2WI2NU
NSC 59257
VEROCHIC
CHEBI:16119
1-Cyclohexene-1-carboxylic acid, 3,4,5-trihydroxy-, (3R-(3alpha,4alpha,5beta))-
SHIKIMIC ACID [MI]
SHIKIMIC ACID [HSDB]
SHIKIMIC ACID [IARC]
[3R-(3alpha,4alpha,5beta)]-3,4,5-Trihydroxy-1-cyclohexene-1-carboxylic acid
DTXSID4032039
EC 205-334-2
NSC-59257
SHIKIMIC ACID (IARC)
1-cyclohexene-1-carboxylic acid, 3,4,5-trihydroxy-
Shikimates
(3r,4s,5r)-3,4,5-trihydroxy-1-cyclohexene-1-carboxylic acid
Acid, Shikimic
SHIKIMIC ACID (CONSTITUENT OF CRANBERRY LIQUID PREPARATION) [DSC]
Shikimic Acid Derivatives
(3R-(3alpha,4alpha,5beta))-3,4,5-trihydroxy-1-cyclohexene-1-carboxylic acid
() Shikimic acid
SHIKIMIC ACID [INCI]
DTXCID2012039
3,4,5Trihydroxy1cyclohexene1carboxylic acid
(3R,4S,5R)3,4,5Trihydroxycyclohex1enecarboxylic acid
3alpha,4alpha,5betaTrihydroxy1cyclohexene1carboxylic acid
SHIKIMIC ACID (CONSTITUENT OF CRANBERRY LIQUID PREPARATION)
1Cyclohexene1carboxylic acid, 3,4,5trihydroxy, (3R(3alpha,4alpha,5beta))
1-Cyclohexene-1-carboxylic acid, 3,4,5-trihydroxy-, (3R-(3alpha,4alpha,5beta))-(9CI)
Shikimate
(-)-Shikimic acid
ShikimicAcid
(-)-Shikimate
MFCD00066278
106210-02-0
CHEMBL290345
HYDROTRIS(3-PHENYLPYRAZOL-1-YL)BORATE THALLIUM SALT
3,4,5-Trihydroxy-1-cyclohexenecarboxylic acid
(3R,4S,5R)-(-)-3,4,5-Trihydroxy-1-cyclohexenecarboxylic acid
C7H10O5
SMR001306700
SR-01000632403
UNII-29MS2WI2NU
Skikimate
L-Shikimate
2aay
4guj
Spectrum_001232
1we2
2aa9
SpecPlus_000488
Spectrum2_001508
Spectrum3_001541
Spectrum4_001853
Spectrum5_000386
Shikimic acid (Standard)
Shikimic acid, >=99%
Bmse000114
SCHEMBL43377
BSPBio_002982
KBioGR_002287
KBioSS_001712
MLS002207031
MLS004256600
DivK1c_006584
SPECTRUM1502256
SPBio_001555
MEGxp0_001939
HY-N0130R
KBio1_001528
KBio2_001712
KBio2_004280
KBio2_006848
KBio3_002482
(4S,3R,5R)-3,4,5-trihydroxycyclohex-1-enecarboxylic acid
Shikimic acid, analytical standard
HY-N0130
MSK40056
BDBM50281998
CCG-38884
AKOS004119897
AC-8010
FS06909
SDCCGMLS-0066740.P001
SMP1_000326
NCGC00142601-01
NCGC00142601-02
1ST40056
AS-13905
CS-0007856
NS00079355
S0038
C00493
EN300-208879
Q410830
SR-01000632403-1
SR-01000632403-4
SR-01000632403-5
(-)-3,4,5-Trihydroxy-1-cyclohexene-1-carboxylic acid
Z1198149969
(3R,4S,5R)-3,4,5-trihydroxycyclohexene-1-carboxylicacid
B1A53F8A-8664-405D-8370-A9785ADD2D0B
(3R,4S,5R)-(-)-3,4,5-Trihydroxy-1-cyclohexene-1-carboxylic Acid
(3R,4S,5R))-3,4,5-Trihydroxy-1-cyclohexenecarboxylic acid
1-Cyclohexene-1-carboxylic acid, 3,4,5-trihydroxy-, (3R,4S,5R)- (9CI)
[3R-(3 alpha,4 alpha,5 beta)]-3,4,5-Trihydroxy-1-cyclohexene-1-carboxylic acid
1-Cyclohexene-1-carboxylic acid, 3,4,5-trihydroxy-, (3R-(3alpha,4alpha,5beta))
1-Cyclohexene-1-carboxylic acid, 3,4,5-trihydroxy-, (3R-(3alpha,4alpha,5beta))- (9CI)
Shikimic acid [3R-(3alpha,4alpha,5beta)]-3,4,5-Trihydroxy-1-cyclohexene-1-carboxylic acid
InChI=1/C7H10O5/c8-4-1-3(7(11)12)2-5(9)6(4)10/h1,4-6,8-10H,2H2,(H,11,12)/t4-,5-,6-/m1/s
Pubchem:
8742
Cas:
138-59-0
Gnps:
CCMSLIB00000212371
Zinc:
ZINC000003860720
Kegg Ligand:
C00493
Chebi:
16119
Nmrshiftdb2:
20096803
Metabolights:
MTBLC16119
Chembl:
CHEMBL290345
Comptox:
DTXSID4032039
Pdb Ligand:
SKM
Bindingdb:
50281998
CPRiL:
46833
SMILES: C1=CCCCC1
Level: 0
Mol. Weight: 174.15 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -5.52
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -3.49
- Human Oral Bioavailability 50%
- Non-Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -2.13
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Non-Penetrable
- Fraction Unbound (Human)
- 0.43
- Plasma Protein Binding
- 22.44
- 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
- 1.57
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- -1.52
- Biodegradation
- Toxic
- Carcinogenesis
- Safe
- Crustacean
- Safe
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Toxic
- Maximum Tolerated Dose
- 1.8
- Liver Injury II
- Safe
- hERG Blockers
- Safe
- Daphnia Maga
- 2.35
- 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
- -2.99
- Rat (Acute)
- 0.92
- Rat (Chronic Oral)
- 2.97
- Fathead Minnow
- 2.76
- Respiratory Disease
- Safe
- Skin Sensitisation
- Toxic
- SR-ARE
- Safe
- SR-ATAD5
- Safe
- SR-HSE
- Safe
- SR-MMP
- Safe
- SR-p53
- Safe
General Properties
- Boiling Point
- 363.44
- Hydration Free Energy
- -18.91
- Log(D) at pH=7.4
- -3.39
- Log(P)
- -1.96
- Log S
- -0.19
- Log(Vapor Pressure)
- -9.18
- Melting Point
- 156.31
- pKa Acid
- 3.94
- pKa Basic
- 5.34
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Macrophage metalloelastase | P39900 | MMP12_HUMAN | Homo sapiens | 3 | 0.8990 |
| Macrophage metalloelastase | P39900 | MMP12_HUMAN | Homo sapiens | 3 | 0.8990 |
| 3-dehydroquinate dehydratase | P9WPX7 | AROQ_MYCTU | Mycobacterium tuberculosis | 3 | 0.8962 |
| 3-dehydroquinate dehydratase | P9WPX7 | AROQ_MYCTU | Mycobacterium tuberculosis | 3 | 0.8962 |
| Pyridoxal kinase, putative | C4LVZ4 | C4LVZ4_ENTHI | Entamoeba histolytica | 3 | 0.8653 |
| Pyridoxal kinase, putative | C4LVZ4 | C4LVZ4_ENTHI | Entamoeba histolytica | 3 | 0.8653 |
| ADP-ribosylation factor 1 | P84077 | ARF1_HUMAN | Homo sapiens | 2 | 0.8103 |
| ADP-ribosylation factor 1 | P84077 | ARF1_HUMAN | Homo sapiens | 2 | 0.8103 |
| Trichothecene 15-O-acetyltransferase TRI3 | Q9C1B7 | TRI3_FUSSP | Fusarium sporotrichioides | 3 | 0.7702 |
| Trichothecene 15-O-acetyltransferase TRI3 | Q9C1B7 | TRI3_FUSSP | Fusarium sporotrichioides | 3 | 0.7702 |
| Shikimate dehydrogenase (NADP(+)) | P56119 | AROE_HELPY | Helicobacter pylori | 3 | 0.7527 |
| Shikimate dehydrogenase (NADP(+)) | P56119 | AROE_HELPY | Helicobacter pylori | 3 | 0.7527 |
| Shikimate kinase | P9WPY3 | AROK_MYCTU | Mycobacterium tuberculosis | 3 | 0.7395 |
| Shikimate kinase | P9WPY3 | AROK_MYCTU | Mycobacterium tuberculosis | 3 | 0.7395 |
| ADP-ribosylation factor 1 | P84080 | ARF1_BOVIN | Bos taurus | 2 | 0.7134 |
| ADP-ribosylation factor 1 | P84080 | ARF1_BOVIN | Bos taurus | 2 | 0.7134 |