Natural Product: NPC167577

Natural Product IDNPC167577
Common Name
?
The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
 Ethyl Cinnamate
IUPAC Name ethyl (E)-3-phenylprop-2-enoate
Synonyms Ethyl Cinnamate
Synthetic Gene Cluster n.a.
ChEMBL Identifier CHEMBL318196
PubChem CID 637758
Chemical Classification
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000261] Phenylpropanoids and polyketides
      • [CHEMONTID:0000476] Cinnamic acids and derivatives
        • [CHEMONTID:0003480] Cinnamic acid esters

The Chemical Classification was calculated by Classyfire, a software for chemical taxonomy calculation. Reference: DOI:10.1186/s13321-016-0174-y.

  Chemical Representations

Standard InCHIKey KBEBGUQPQBELIU-CMDGGOBGSA-N
Standard InCHI InChI=1S/C11H12O2/c1-2-13-11(12)9-8-10-6-4-3-5-7-10/h3-9H,2H2,1H3/b9-8+
SMILES CCOC(=O)/C=C/c1ccccc1

  Calculated Properties

Physi-Chem Properties

Molecular Weight:   176.08 Volume:   194.654
?
Van der Waals volume.
Dense:   0.905 LogP:   2.864
?
The logarithm of the n-octanol/water distribution coefficients.
logD7.4:   2.543
?
The logarithm of the n-octanol/water distribution coefficient at pH=7.4.
 LogS:   -2.889
?
The logarithm of aqueous solubility value.
Rotatable Bonds:   4.0 Rigid Bonds:   8.0
TPSA:   26.3
?
Topological Polar Surface Area.
 H-Bond Acceptor:   2.0
H-Bond Donor:   0.0 Rings:   1.0
Heavy Atoms:   2.0

MedChem Properties

QED Drug-Likeness Score:   0.521 GASA:   0.0
?
GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:   1.585 Fsp3:   0.182
MCE-18:   5.0
?
MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.
 Lipinski Rule-of-5:   Rejected
Pfizer Rule:   Rejected GSK Rule:   Rejected
Golden Triangle Rule:   Accepted BMS Rule:   0
Chelating Alert:   0 PAINS Alert:   0
Colloidal aggregators:   0.431 Fluc inhibitor:   0.947
?
The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:   0.084
?
The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1
 Green fluorescence:   0.344
?
The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:   0.997 Promiscuous compounds:   0.461

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:   -4.822 MDCK Permeability:   -4.441
Pgp-inhibitor:   0.991 Pgp-substrate:   0.005
PAMPA:   0.076
?
The experimental data for Peff was logarithmically transformed (logPeff). Molecules with log Peff values below 2.0 were classified as low-permeability (Category 0), while those with log Peff values exceeding 2.5 were classified as high-permeability (Category 1).
 Human Intestinal Absorption (HIA):   0.015
20% Bioavailability (F20%):   0.376 30% Bioavailability (F30%):   0.563
50% Bioavailability (F50%):   0.462

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):   0.524 MRP1:   0.134
Plasma Protein Binding (PPB):   95.769% Volume Distribution (VD):   0.002
Fu: 5.091%
?
The fraction unbound in plasms.
 OATP1B1 inhibitor:   0.93
OATP1B3 inhibitor:   0.992 BCRP inhibitor:   0.023
BSEP inhibitor:   0.996

ADMET: Metabolism

CYP1A2-inhibitor:   0.0 CYP1A2-substrate:   0.995
CYP2C19-inhibitor:   0.0 CYP2C19-substrate:   0.962
CYP2C9-inhibitor:   0.004 CYP2C9-substrate:   0.189
CYP2D6-inhibitor:   0.001 CYP2D6-substrate:   0.002
CYP3A4-inhibitor:   0.0 CYP3A4-substrate:   1.0
CYP2B6-substrate:   0.0 CYP2C8-inhibitor:   1.0
HLM stability:   0.379
?
Human liver microsomal (HLM) stability. Category 0: stable+ (HLM > 30 min); Category 1: unstable- (HLM ≤ 30 min). The output value is the probability of human liver microsomal instability, where a value closer to 1 indicates a higher likelihood of instability.

ADMET: Excretion

Clearance (CL):  10.604 Half-life (T1/2):  0.758

ADMET: Toxicity

hERG Blockers:  0.194 hERG Blockers (10um):  0.519
Human Hepatotoxicity (H-HT):  0.355 Drug-induced Liver Injury (DILI):  0.53
AMES Toxicity:  0.272 Rat Oral Acute Toxicity:  0.043
Maximum Recommended Daily Dose:  0.29 Skin Sensitization:  0.941
Carcinogencity:  0.223 Eye Corrosion:  0.717
Eye Irritation:  0.994 Respiratory Toxicity:  0.166
Drug-induced Neurotoxicity:  0.354 Ototoxicity:  0.094
Hematotoxicity:  0.024 Drug-induced Nephrotoxicity:  0.143
Genotoxicity:  0.016 RPMI-8226 Immunitoxicity:  0.037
A549 Cytotoxicity:  0.04 Hek293 Cytotoxicity:  0.231
BCF:   1.317
?
Bioconcentration factors are used for considering secondary poisoning potential and assessing risks to human health via the food chain. The unit is -log10[(mg/L)/(1000*MW)].
 IGC50:   4.035
?
48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:   5.135
?
48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].
 LC50FM:   4.787
?
96 hour fathead minnow LC50. The unit of LC50FM is -log10[(mg/L)/(1000*MW)].

  Species Source

Organism ID Organism Name Taxonomy Level Family SuperKingdom Isolation Part Collection Location Collection Time Reference
NPO26650 Terminalia chebula Species Combretaceae Eukaryota n.a. n.a. n.a. PMID[11520216]
NPO3987 Syzygium aromaticum Species Myrtaceae Eukaryota n.a. n.a. n.a. PMID[1402962]
NPO12830 Styrax tonkinensis Species Styracaceae Eukaryota resin n.a. n.a. PMID[16724846]
NPO14969 Hedychium spicatum Species Zingiberaceae Eukaryota n.a. rhizome n.a. PMID[19027298]
NPO14969 Hedychium spicatum Species Zingiberaceae Eukaryota rhizomes n.a. n.a. PMID[19332371]
NPO31458 Cinnamomum cassia Species Lauraceae Eukaryota twigs n.a. n.a. PMID[19555125]
NPO14969 Hedychium spicatum Species Zingiberaceae Eukaryota rhizomes n.a. n.a. PMID[19782567]
NPO31458 Cinnamomum cassia Species Lauraceae Eukaryota twigs n.a. n.a. PMID[22677314]
NPO14969 Hedychium spicatum Species Zingiberaceae Eukaryota n.a. rhizome n.a. PMID[23422227]
NPO16850 Eucommia ulmoides Species Eucommiaceae Eukaryota n.a. bark n.a. PMID[26767291]
NPO16850 Eucommia ulmoides Species Eucommiaceae Eukaryota n.a. n.a. n.a. PMID[26767291]
NPO3987 Syzygium aromaticum Species Myrtaceae Eukaryota Flower Buds n.a. n.a. PMID[26977531]
NPO542 Artemisia absinthium Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[33588649]
NPO31458 Cinnamomum cassia Species Lauraceae Eukaryota n.a. n.a. n.a. PMID[34332066]
NPO47170 Artemisia pallens Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[34669255]
NPO3987 Syzygium aromaticum Species Myrtaceae Eukaryota n.a. n.a. n.a. PMID[34770801]
NPO14969 Hedychium spicatum Species Zingiberaceae Eukaryota n.a. n.a. n.a. PMID[35481430]
NPO56320 Pinus ponderosa var. ponderosa Species Pinaceae Eukaryota n.a. n.a. n.a. PMID[36080426]
NPO63405 Clinopodium brownei Species Lamiaceae Eukaryota n.a. n.a. n.a. PMID[36838728]
NPO3987 Syzygium aromaticum Species Myrtaceae Eukaryota n.a. n.a. n.a. PMID[36985392]
NPO31458 Cinnamomum cassia Species Lauraceae Eukaryota n.a. n.a. n.a. PMID[37446712]
NPO3987 Syzygium aromaticum Species Myrtaceae Eukaryota n.a. n.a. n.a. PMID[37836118]
NPO542 Artemisia absinthium Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[38538562]
NPO542 Artemisia absinthium Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[38606448]
NPO31458 Cinnamomum cassia Species Lauraceae Eukaryota n.a. n.a. n.a. PMID[38688144]
NPO55669 Artemisia judaica Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[38930948]
NPO542 Artemisia absinthium Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[39598372]
NPO3987 Syzygium aromaticum Species Myrtaceae Eukaryota n.a. n.a. n.a. PMID[39684253]
NPO3987 Syzygium aromaticum Species Myrtaceae Eukaryota n.a. n.a. n.a. PMID[39699537]
NPO3987 Syzygium aromaticum Species Myrtaceae Eukaryota n.a. n.a. n.a. PMID[8904847]
NPO3987 Syzygium aromaticum Species Myrtaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO47170 Artemisia pallens Species Asteraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO22848 Kaempferia galanga Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO14969 Hedychium spicatum Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO12830 Styrax tonkinensis Species Styracaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO11291 Styrax benzoin Species Styracaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO542 Artemisia absinthium Species Asteraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO16850 Eucommia ulmoides Species Eucommiaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO26650 Terminalia chebula Species Combretaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO31458 Cinnamomum cassia Species Lauraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO55669 Artemisia judaica Species Asteraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO3987 Syzygium aromaticum Species Myrtaceae Eukaryota Essential Oil n.a. n.a. Database[FooDB]
NPO3987 Syzygium aromaticum Species Myrtaceae Eukaryota n.a. n.a. Database[FooDB]
NPO3987 Syzygium aromaticum Species Myrtaceae Eukaryota n.a. n.a. Database[FooDB]
NPO3987 Syzygium aromaticum Species Myrtaceae Eukaryota Stem n.a. n.a. Database[FooDB]
NPO3987 Syzygium aromaticum Species Myrtaceae Eukaryota Leaf n.a. n.a. Database[FooDB]
NPO3987 Syzygium aromaticum Species Myrtaceae Eukaryota Fruit n.a. n.a. Database[FooDB]
NPO3987 Syzygium aromaticum Species Myrtaceae Eukaryota Bark n.a. n.a. Database[FooDB]
NPO16850 Eucommia ulmoides Species Eucommiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO11291 Styrax benzoin Species Styracaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO26650 Terminalia chebula Species Combretaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO542 Artemisia absinthium Species Asteraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO3987 Syzygium aromaticum Species Myrtaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO31458 Cinnamomum cassia Species Lauraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO22848 Kaempferia galanga Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO3987 Syzygium aromaticum Species Myrtaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO11291 Styrax benzoin Species Styracaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO14969 Hedychium spicatum Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO26650 Terminalia chebula Species Combretaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO12830 Styrax tonkinensis Species Styracaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO22848 Kaempferia galanga Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO16850 Eucommia ulmoides Species Eucommiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO542 Artemisia absinthium Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO26650 Terminalia chebula Species Combretaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO12830 Styrax tonkinensis Species Styracaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO16850 Eucommia ulmoides Species Eucommiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO31458 Cinnamomum cassia Species Lauraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO11291 Styrax benzoin Species Styracaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO3987 Syzygium aromaticum Species Myrtaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO22848 Kaempferia galanga Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO542 Artemisia absinthium Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO26650 Terminalia chebula Species Combretaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO11291 Styrax benzoin Species Styracaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO12830 Styrax tonkinensis Species Styracaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO16850 Eucommia ulmoides Species Eucommiaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO22848 Kaempferia galanga Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO3987 Syzygium aromaticum Species Myrtaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO22848 Kaempferia galanga Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26650 Terminalia chebula Species Combretaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16850 Eucommia ulmoides Species Eucommiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11291 Styrax benzoin Species Styracaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO542 Artemisia absinthium Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12830 Styrax tonkinensis Species Styracaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3987 Syzygium aromaticum Species Myrtaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14969 Hedychium spicatum Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[UNPD]

Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].



  NP Quantity Composition/Concentration

Organism ID Organism Name Organism Material Preparation Organism Part NP Quantity (Standard) NP Quantity (Minimum) NP Quantity (Maximum) Quantity Unit Reference
NPO47170 Artemisia pallens Oil n.a. 4.9 n.a. n.a. % PMID[34669255]
NPO47170 Artemisia pallens Oil n.a. 5.6 n.a. n.a. % PMID[34669255]
NPO47170 Artemisia pallens Oil n.a. 0.3 n.a. n.a. % PMID[34669255]
NPO542 Artemisia absinthium Headspace solid phase microextraction n.a. 5.4 n.a. n.a. % PMID[39598372]
NPO542 Artemisia absinthium Hydro distillation n.a. 3.7 n.a. n.a. % PMID[39598372]
NPO55669 Artemisia judaica Oil Aerial parts 5.1 n.a. n.a. % PMID[38930948]
NPO55669 Artemisia judaica Oil Aerial parts 12.9 n.a. n.a. % PMID[38930948]
NPO56320 Pinus ponderosa var. ponderosa Oil n.a. 0.2 n.a. n.a. % PMID[36080426]
NPO56320 Pinus ponderosa var. ponderosa Oil n.a. 0.1 n.a. n.a. % PMID[36080426]
NPO63405 Clinopodium brownei Oil Leaves 21.4 n.a. n.a. % PMID[36838728]
NPO63405 Clinopodium brownei Oil Leaves 18.75 n.a. n.a. % PMID[36838728]

Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].



 Biological Activity

Molecular-level activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference

In vitro activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT1970 Cell line THP-1 Homo sapiens IC50 = 41230.0 nM PMID[19782567]
NPT116 Cell line HL-60 Homo sapiens IC50 = 35690.0 nM PMID[19782567]
NPT1083 Cell line A-375 Homo sapiens IC50 = 31590.0 nM PMID[19782567]
NPT81 Cell line A549 Homo sapiens IC50 = 50350.0 nM PMID[19782567]
NPT737 Cell line HUVEC Homo sapiens MTD = 130.0 ug ml-1 PMID[21955679]
NPT737 Cell line HUVEC Homo sapiens Inhibition = 85.0 % PMID[21955679]
NPT737 Cell line HUVEC Homo sapiens IC50 = 95.0 ug.mL-1 PMID[21955679]
NPT2711 Cell line BALB/3T3 Mus musculus Inhibition = 29.09 % PMID[28236590]
NPT722 Organism Athelia rolfsii Athelia rolfsii GI = 36.0 % DOI[10.1584/jpestics.25.263]
NPT722 Organism Athelia rolfsii Athelia rolfsii GI = 63.0 % DOI[10.1584/jpestics.25.263]
NPT722 Organism Athelia rolfsii Athelia rolfsii GI = 14.0 % DOI[10.1584/jpestics.25.263]
NPT28438 Unchecked Unchecked n.a. LC10 = 30.4 ug ml-1 PMID[34225166]
NPT723 Organism Pythium Pythium GI = 57.0 % DOI[10.1584/jpestics.25.263]
NPT20529 Non-molecular NON-PROTEIN TARGET n.a. ED50 > 50.0 ug ml-1 PMID[691008]
NPT2 Others Unspecified n.a. IC50 > 5000000.0 nM PMID[15125954]
NPT21912 Organism Hylobius abietis Hylobius abietis AFI = 83.0 % PMID[17927202]
NPT3934 Organism Brassica rapa subsp. chinensis Brassica rapa subsp. chinensis GI = 26.0 % DOI[10.1584/jpestics.25.263]
NPT3934 Organism Brassica rapa subsp. chinensis Brassica rapa subsp. chinensis GI = 0.0 % DOI[10.1584/jpestics.25.263]

In vivo activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT28438 Unchecked Unchecked n.a. mortality = 95.0 % PMID[34225166]





 Experimental ADME

Experiment Model Experiment Tissue ADME Type ADME Relation ADME Value ADME Unit Reference





 Experimental Toxicity

Quantitative toxicity

Experiment Model Experiment Organism Toxicity Type Toxicity Relation Toxicity Value Toxicity Unit Reference

Common Abbreviations:
LC: Lethal Concentration; LD: Lethal Dose; LT:Lethal Time; NOAEL: No-observed-adverse-effect Level; BMDL: Benchmark Dose Lower Confidence Limit; BMD: Benchmark Dose; BMC:Benchmark Concentration; LOAEL: Lowest Observed Adverse Effect Level; RfD:Reference Dose; RfC:Reference Concentration; MRL: Minimal Risk Level; MEG: Maximum Exposure Guideline; PAC: Protective Action Criteria

Categorical toxicity labels

Hepatotoxicity Carcinogenicity Mutagenicity Cardiotoxicity Respiratory Toxicity Eye Irritation Endocrine Disruption
Hepatotoxicity Carcinogenicity Mutagenicity Cardiotoxicity Respiratory Toxicity Eye Irritation Endocrine Disruption

Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP toxicity records from domain-specific databases. These databases include:
☉ ToxValDB: a curated database that compiles quantitative toxicity values for chemicals from diverse public sources to support toxicological research and risk assessment.
☉ TOXRIC: a comprehensive, free-to-access, online database providing toxicological/feature data. The toxicity labels are retrieved from this database. [PMID: 36400569]


  Chemically structural similarity

Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes approximately 50,000 NPs with experimentally-derived bioactivity available in NPASS)

Similarity is measured using the Tanimoto coefficient (Tc) , which compares the binary fingerprints of two molecules. Tc is calculated as the intersection divided by the union of '1' bits in the fingerprints, ranging from 0 to 1, with 1 indicating highest similarity.

●  The left chart: Distribution of similarity level between NPC167577 and all remaining natural products in the NPASS database.
●  The right table: Most similar natural products (Tc>=0.5 or Top200).

Similarity Score Similarity Level Natural Product ID

Similar Clinical/Approved Drugs

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules.

●  The left chart: Distribution of similarity level between NPC167577 and all drugs/candidates.
●  The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

Similarity Score Similarity Level Drug ID Developmental Stage

Bioactivity similarity

  Bioactivity similarity

Similar Natural Products in NPASS

Similarity level is defined by Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.
Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity
B: biological targets similarity
C: networks similarity
D: cell-based bioactivity similarity
E: similarity based on clinical data