Select a section from the left sidebar
Dorstenone
- Family: Plantae - Moraceae
- Kingdom: Plantae
-
Class: Terpenoid
- Subclass: Terpene
| Canonical Smiles | CC(=CCc1c(O)ccc(c1O)C(=O)[C@@H]1[C@H](C=C(C[C@H]1c1ccc(cc1)O)C)c1c(O)ccc(c1O)C(=O)/C=C/c1ccc(cc1)O)C |
|---|---|
| InChI | InChI=1S/C40H38O8/c1-22(2)4-14-28-34(44)18-16-30(38(28)46)40(48)36-31(25-8-12-27(42)13-9-25)20-23(3)21-32(36)37-35(45)19-15-29(39(37)47)33(43)17-7-24-5-10-26(41)11-6-24/h4-13,15-19,21,31-32,36,41-42,44-47H,14,20H2,1-3H3/b17-7+/t31-,32-,36-/m0/s1 |
| InChIKey | SUQUIVSLHDOSQP-NOLCOJBVSA-N |
| Formula | C40H38O8 |
| HBA | 8 |
| HBD | 6 |
| MW | 646.74 |
| Rotatable Bonds | 9 |
| TPSA | 155.52 |
| LogP | 8.04 |
| Number Rings | 5 |
| Number Aromatic Rings | 4 |
| Heavy Atom Count | 48 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.2 |
| Exact Mass | 646.26 |
| Number of Lipinski Rule Violations | 3 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Dorstenia barteri | Moraceae | Plantae | 2604977 |
Showing of synonyms
Dorstenone
SCHEMBL15400091
(E)-1-[3-[(1S,5R,6S)-6-[2,4-dihydroxy-3-(3-methylbut-2-enyl)benzoyl]-5-(4-hydroxyphenyl)-3-methylcyclohex-2-en-1-yl]-2,4-dihydroxyphenyl]-3-(4-hydroxyphenyl)prop-2-en-1-one
No compound-protein relationship available.
SMILES: c1ccccc1C=CC(=O)c2cc(ccc2)C(C3C(=O)c4ccccc4)C=CCC3c5ccccc5
Level: 4
Mol. Weight: 646.74 g/mol
SMILES: c1ccccc1C=CC(=O)c2cc(ccc2)C(C=CCC3)C3C(=O)c4ccccc4
Level: 3
Mol. Weight: 646.74 g/mol
SMILES: c1ccccc1C=CC(=O)c2cc(ccc2)C3C=CCC(C3)c4ccccc4
Level: 3
Mol. Weight: 646.74 g/mol
SMILES: c1ccccc1C(=O)C2C(c3ccccc3)C=CCC2c4ccccc4
Level: 3
Mol. Weight: 646.74 g/mol
SMILES: c1ccccc1C=CC(=O)c2cc(ccc2)C3C=CCCC3
Level: 2
Mol. Weight: 646.74 g/mol
SMILES: c1ccccc1C(=O)C2CCC=CC2c3ccccc3
Level: 2
Mol. Weight: 646.74 g/mol
SMILES: c1ccccc1C(=O)C2C(CC=CC2)c3ccccc3
Level: 2
Mol. Weight: 646.74 g/mol
SMILES: c1ccccc1C2C=CCC(C2)c3ccccc3
Level: 2
Mol. Weight: 646.74 g/mol
SMILES: c1ccccc1C(=O)C=Cc2ccccc2
Level: 1
Mol. Weight: 646.74 g/mol
SMILES: C1CC=CCC1C(=O)c2ccccc2
Level: 1
Mol. Weight: 646.74 g/mol
SMILES: c1ccccc1C2CC=CCC2
Level: 1
Mol. Weight: 646.74 g/mol
SMILES: c1ccccc1C2C=CCCC2
Level: 1
Mol. Weight: 646.74 g/mol
SMILES: C1=CCCCC1
Level: 0
Mol. Weight: 646.74 g/mol
SMILES: c1ccccc1
Level: 0
Mol. Weight: 646.74 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -5.73
- Human Oral Bioavailability 20%
- Non-Bioavailable
- Human Intestinal Absorption
- Non-Absorbed
- Madin-Darby Canine Kidney
- -4.65
- Human Oral Bioavailability 50%
- Non-Bioavailable
- P-Glycoprotein Inhibitor
- Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- 91.78
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Non-Penetrable
- Fraction Unbound (Human)
- 1.23
- Plasma Protein Binding
- 106.26
- 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
- Inhibitor
- CYP 2C9 Substrate
- Substrate
- CYP 2D6 Inhibitor
- Inhibitor
- CYP 2D6 Substrate
- Non-Substrate
- CYP 3A4 Inhibitor
- Non-Inhibitor
- CYP 3A4 Substrate
- Non-Substrate
- OATP1B1
- Inhibitor
- OATP1B3
- Inhibitor
Excretion
- Clearance
- 9.0
- Organic Cation Transporter 2
- Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- -0.65
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Toxic
- Liver Injury I (DILI)
- Toxic
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- 1.04
- Liver Injury II
- Toxic
- hERG Blockers
- Toxic
- Daphnia Maga
- 7.55
- Micronucleos
- Toxic
- NR-AhR
- Safe
- NR-AR
- Safe
- NR-AR-LBD
- Safe
- NR-Aromatase
- Safe
- NR-ER
- Toxic
- NR-ER-LBD
- Safe
- NR-GR
- Toxic
- NR-PPAR-gamma
- Safe
- NR-TR
- Toxic
- T. Pyriformis
- -166824.18
- Rat (Acute)
- 2.32
- Rat (Chronic Oral)
- 3.92
- Fathead Minnow
- 226.73
- Respiratory Disease
- Toxic
- Skin Sensitisation
- Safe
- SR-ARE
- Toxic
- SR-ATAD5
- Safe
- SR-HSE
- Safe
- SR-MMP
- Toxic
- SR-p53
- Toxic
General Properties
- Boiling Point
- 12146.13
- Hydration Free Energy
- -2.92
- Log(D) at pH=7.4
- 4.88
- Log(P)
- 8.94
- Log S
- -7.52
- Log(Vapor Pressure)
- -439.84
- Melting Point
- 253.15
- pKa Acid
- 6.44
- pKa Basic
- 8.86
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Histone deacetylase 4 | P56524 | HDAC4_HUMAN | Homo sapiens | 3 | 0.9433 |
| Dihydrofolate reductase | P00378 | DYR_CHICK | Gallus gallus | 3 | 0.9221 |
| NADPH-dependent oxidoreductase 2-alkenal reductase | Q39172 | AER_ARATH | Arabidopsis thaliana | 3 | 0.9182 |
| Valacyclovir hydrolase | Q86WA6 | BPHL_HUMAN | Homo sapiens | 3 | 0.8690 |
| Bifunctional epoxide hydrolase 2 | P34913 | HYES_HUMAN | Homo sapiens | 3 | 0.8566 |
| Soluble acetylcholine receptor | Q8WSF8 | Q8WSF8_APLCA | Aplysia californica | 3 | 0.8439 |
| D-aminoacyl-tRNA deacylase | Q8IIS0 | DTD_PLAF7 | Plasmodium falciparum | 3 | 0.8314 |
| Chitinase A | Q9AMP1 | Q9AMP1_VIBHA | Vibrio harveyi | 3 | 0.8190 |
| Serpin domain-containing protein | H0ZQY2 | H0ZQY2_TAEGU | Taeniopygia guttata | 3 | 0.8134 |
| Polyribonucleotide nucleotidyltransferase | A7ZS61 | PNP_ECO24 | Escherichia coli O139:H28 | 4 | 0.8126 |
| Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha | Q04631 | FNTA_RAT | Rattus norvegicus | 3 | 0.8097 |
| Nuclear receptor subfamily 4immunitygroup A member 1 | P22736 | NR4A1_HUMAN | Homo sapiens | 3 | 0.8059 |
| Matrilysin | P09237 | MMP7_HUMAN | Homo sapiens | 3 | 0.8015 |
| Cathepsin S | P25774 | CATS_HUMAN | Homo sapiens | 3 | 0.7963 |
| Beta-secretase 1 | P56817 | BACE1_HUMAN | Homo sapiens | 3 | 0.7962 |
| Urokinase-type plasminogen activator | P00749 | UROK_HUMAN | Homo sapiens | 3 | 0.7871 |
| Geranylgeranyl transferase type-2 subunit alpha | Q08602 | PGTA_RAT | Rattus norvegicus | 3 | 0.7747 |
| Threonine--tRNA ligase | P0A8M3 | SYT_ECOLI | Escherichia coli | 3 | 0.7692 |
| Serine/threonine-protein kinase Chk1 | O14757 | CHK1_HUMAN | Homo sapiens | 3 | 0.7647 |
| Protease | O38896 | O38896_9HIV1 | Human immunodeficiency virus 1 | 3 | 0.7629 |
| Ephrin type-A receptor 2 | P29317 | EPHA2_HUMAN | Homo sapiens | 3 | 0.7598 |
| Gag-Pol polyprotein | P03367 | POL_HV1BR | Human immunodeficiency virus type 1 group M subtype B | 3 | 0.7572 |
| Acetylcholinesterase | P21836 | ACES_MOUSE | Mus musculus | 3 | 0.7561 |
| Death-associated protein kinase 1 | P53355 | DAPK1_HUMAN | Homo sapiens | 4 | 0.7504 |
| Death-associated protein kinase 1 | P53355 | DAPK1_HUMAN | Homo sapiens | 4 | 0.7478 |
| Gag-Pol polyprotein | P12497 | POL_HV1N5 | Human immunodeficiency virus type 1 group M subtype B | 3 | 0.7476 |
| Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha | Q04631 | FNTA_RAT | Rattus norvegicus | 3 | 0.7373 |
| Epidermal growth factor receptor | P00533 | EGFR_HUMAN | Homo sapiens | 3 | 0.7331 |
| 3',5'-cyclic-AMP phosphodiesterase 4D | Q08499 | PDE4D_HUMAN | Homo sapiens | 3 | 0.7322 |
| Seminal ribonuclease | P00669 | RNS_BOVIN | Bos taurus | 3 | 0.7298 |
| Urokinase-type plasminogen activator | P00749 | UROK_HUMAN | Homo sapiens | 3 | 0.7285 |
| Acyl-CoA:acyl-CoA alkyltransferase | Q8PDX2 | OLEA_XANCP | Xanthomonas campestris pv. campestris | 3 | 0.7247 |
| Death-associated protein kinase 1 | P53355 | DAPK1_HUMAN | Homo sapiens | 4 | 0.7223 |
| C-1-tetrahydrofolate synthase, cytoplasmic | P11586 | C1TC_HUMAN | Homo sapiens | 3 | 0.7217 |
| Dihydrofolate reductase | P0ABQ4 | DYR_ECOLI | Escherichia coli | 4 | 0.7197 |
| S-adenosylmethionine decarboxylase proenzyme | P17707 | DCAM_HUMAN | Homo sapiens | 3 | 0.7181 |
| 17beta-hydroxysteroid dehydrogenase | O93874 | O93874_COCLU | Cochliobolus lunatus | 3 | 0.7178 |
| Beta-secretase 1 | P56817 | BACE1_HUMAN | Homo sapiens | 3 | 0.7174 |
| Lactotransferrin | P24627 | TRFL_BOVIN | Bos taurus | 3 | 0.7145 |
| Prothrombin | P00734 | THRB_HUMAN | Homo sapiens | 2 | 0.7143 |
| Endothiapepsin | P11838 | CARP_CRYPA | Cryphonectria parasitica | 2 | 0.7137 |
| Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha | Q4WP27 | Q4WP27_ASPFU | Aspergillus fumigatus | 3 | 0.7134 |
| Endoplasmin | P41148 | ENPL_CANLF | Canis lupus familiaris | 3 | 0.7131 |
| Serine/threonine-protein kinase pim-1 | P11309 | PIM1_HUMAN | Homo sapiens | 3 | 0.7106 |
| Death-associated protein kinase 1 | P53355 | DAPK1_HUMAN | Homo sapiens | 4 | 0.7096 |
| Basic phospholipase A2 VRV-PL-VIIIa | P59071 | PA2B8_DABRR | Daboia russelii | 2 | 0.7080 |
| Neuropilin-1 | O14786 | NRP1_HUMAN | Homo sapiens | 4 | 0.7078 |
| IOMT 3 | Q06YR3 | Q06YR3_MEDTR | Medicago truncatula | 3 | 0.7072 |
| Lactotransferrin | P24627 | TRFL_BOVIN | Bos taurus | 2 | 0.7045 |
| High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A | O76083 | PDE9A_HUMAN | Homo sapiens | 3 | 0.7044 |
| Cytidine and deoxycytidylate deaminase zinc-binding region | Q82Y41 | Q82Y41_NITEU | Nitrosomonas europaea | 3 | 0.7025 |
| Coagulation factor X | P00742 | FA10_HUMAN | Homo sapiens | 3 | 0.7017 |
| Gag-Pol polyprotein | P12497 | POL_HV1N5 | Human immunodeficiency virus type 1 group M subtype B | 3 | 0.7015 |