Natural Product: NPC36616

Natural Product IDNPC36616
Common Name
?
The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
 Pinifolic Acid
IUPAC Name (1R,4aR,5S,8aR)-5-[(3S)-4-carboxy-3-methylbutyl]-1,4a-dimethyl-6-methylidene-3,4,5,7,8,8a-hexahydro-2H-naphthalene-1-carboxylic acid
Synonyms Pinifolic Acid
Synthetic Gene Cluster n.a.
ChEMBL Identifier CHEMBL2048915
PubChem CID 12314311
Chemical Classification
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0000259] Prenol lipids
        • [CHEMONTID:0001551] Diterpenoids

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 HPQKNJHVWUWAOR-QBSBYYDBSA-N
Standard InCHI InChI=1S/C20H32O4/c1-13(12-17(21)22)6-8-15-14(2)7-9-16-19(15,3)10-5-11-20(16,4)18(23)24/h13,15-16H,2,5-12H2,1,3-4H3,(H,21,22)(H,23,24)/t13-,15-,16+,19+,20+/m0/s1
SMILES C[C@@H](CC[C@H]1C(=C)CC[C@@H]2[C@]1(C)CCC[C@@]2(C)C(=O)O)CC(=O)O

  Calculated Properties

Physi-Chem Properties

Molecular Weight:   336.23 Volume:   364.615
?
Van der Waals volume.
Dense:   0.922 LogP:   3.805
?
The logarithm of the n-octanol/water distribution coefficients.
logD7.4:   2.914
?
The logarithm of the n-octanol/water distribution coefficient at pH=7.4.
 LogS:   -3.761
?
The logarithm of aqueous solubility value.
Rotatable Bonds:   6.0 Rigid Bonds:   14.0
TPSA:   74.6
?
Topological Polar Surface Area.
 H-Bond Acceptor:   4.0
H-Bond Donor:   2.0 Rings:   2.0
Heavy Atoms:   4.0

MedChem Properties

QED Drug-Likeness Score:   0.687 GASA:   1.0
?
GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:   4.11 Fsp3:   0.8
MCE-18:   45.0
?
MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.
 Lipinski Rule-of-5:   Rejected
Pfizer Rule:   Accepted GSK Rule:   Rejected
Golden Triangle Rule:   Rejected BMS Rule:   0
Chelating Alert:   0 PAINS Alert:   0
Colloidal aggregators:   0.152 Fluc inhibitor:   0.0
?
The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:   0.004
?
The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1
 Green fluorescence:   0.001
?
The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:   0.897 Promiscuous compounds:   0.19

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:   -4.958 MDCK Permeability:   -4.914
Pgp-inhibitor:   0.0 Pgp-substrate:   0.0
PAMPA:   0.99
?
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):   0.001
20% Bioavailability (F20%):   0.024 30% Bioavailability (F30%):   0.008
50% Bioavailability (F50%):   0.116

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):   0.01 MRP1:   0.989
Plasma Protein Binding (PPB):   97.4% Volume Distribution (VD):   -0.615
Fu: 2.867%
?
The fraction unbound in plasms.
 OATP1B1 inhibitor:   0.996
OATP1B3 inhibitor:   0.995 BCRP inhibitor:   0.0
BSEP inhibitor:   0.619

ADMET: Metabolism

CYP1A2-inhibitor:   0.002 CYP1A2-substrate:   0.0
CYP2C19-inhibitor:   0.177 CYP2C19-substrate:   0.0
CYP2C9-inhibitor:   0.661 CYP2C9-substrate:   0.0
CYP2D6-inhibitor:   0.0 CYP2D6-substrate:   0.0
CYP3A4-inhibitor:   0.36 CYP3A4-substrate:   0.0
CYP2B6-substrate:   0.003 CYP2C8-inhibitor:   0.003
HLM stability:   0.13
?
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):  1.152 Half-life (T1/2):  1.207

ADMET: Toxicity

hERG Blockers:  0.008 hERG Blockers (10um):  0.01
Human Hepatotoxicity (H-HT):  0.669 Drug-induced Liver Injury (DILI):  0.648
AMES Toxicity:  0.124 Rat Oral Acute Toxicity:  0.395
Maximum Recommended Daily Dose:  0.182 Skin Sensitization:  0.963
Carcinogencity:  0.425 Eye Corrosion:  0.876
Eye Irritation:  0.955 Respiratory Toxicity:  0.801
Drug-induced Neurotoxicity:  0.063 Ototoxicity:  0.661
Hematotoxicity:  0.541 Drug-induced Nephrotoxicity:  0.955
Genotoxicity:  0.623 RPMI-8226 Immunitoxicity:  0.031
A549 Cytotoxicity:  0.012 Hek293 Cytotoxicity:  0.02
BCF:   0.785
?
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:   3.694
?
48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:   5.089
?
48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].
 LC50FM:   4.072
?
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
NPO17593 Pinus sylvestris Species Pinaceae Eukaryota n.a. n.a. n.a. DOI[10.1023/A:1025674116183]
NPO6836 Alpinia blepharocalyx Species Zingiberaceae Eukaryota seeds Mengha, Yunnan Province, China 1991-Aug PMID[11277741]
NPO6836 Alpinia blepharocalyx Species Zingiberaceae Eukaryota seeds n.a. n.a. PMID[11325233]
NPO6836 Alpinia blepharocalyx Species Zingiberaceae Eukaryota Seeds n.a. n.a. PMID[11430002]
NPO3261 Aplysina archeri Species Aplysinidae Eukaryota n.a. n.a. n.a. PMID[1324982]
NPO6457 Pinus strobus Species Pinaceae Eukaryota n.a. heartwood n.a. PMID[13465274]
NPO17593 Pinus sylvestris Species Pinaceae Eukaryota n.a. n.a. n.a. PMID[1536925]
NPO14054 Penicillium janczewskii Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[16180822]
NPO422 Euphorbia cornigera Species Euphorbiaceae Eukaryota n.a. n.a. n.a. PMID[17512094]
NPO422 Euphorbia cornigera Species Euphorbiaceae Eukaryota n.a. n.a. n.a. PMID[19376614]
NPO32774 Copaifera Genus Fabaceae Eukaryota n.a. n.a. n.a. PMID[22440015]
NPO17593 Pinus sylvestris Species Pinaceae Eukaryota n.a. seed n.a. PMID[24225786]
NPO2697 Monodora tenuifolia Species Annonaceae Eukaryota n.a. n.a. n.a. PMID[3509958]
NPO11747 Ocimum tenuiflorum Species Lamiaceae Eukaryota n.a. n.a. n.a. PMID[39073007]
NPO6836 Alpinia blepharocalyx Species Zingiberaceae Eukaryota n.a. n.a. n.a. PMID[9461664]
NPO5975 Aspergillus carneus Species Aspergillaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO18993 Araiostegiella perdurans Species Davalliaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO3261 Aplysina archeri Species Aplysinidae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO3554 Aonidiella aurantii Species Diaspididae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO4564 Anguilla japonica Species Anguillidae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO5584 Aldisa sanguinea Species Dorididae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO4274 Alcyonium utinomii Species Alcyoniidae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO24089 Alcea rosea Species Malvaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO6457 Pinus strobus Species Pinaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO6836 Alpinia blepharocalyx Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO25760 Aspergillus striatus Species Aspergillaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO1390 Melolontha melolontha Species Scarabaeidae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO5261 Sideroxylon cubense Species Sapotaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO3743 Sideritis brevibracteata Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO4949 Salvia yosgadensis Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO7606 Salacia lehmbachii Species Celastraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO1489 Pseudoplexaura flagellosa Species Plexauridae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO8058 Pluchea odorata Species Asteraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO17593 Pinus sylvestris Species Pinaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO14054 Penicillium janczewskii Species Aspergillaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO11747 Ocimum tenuiflorum Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO2993 Nototodarus sloanii Species Ommastrephidae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO2697 Monodora tenuifolia Species Annonaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO2408 Millettia laurentii Species Fabaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO3408 Viguiera decurrens Species Asteraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO3956 Maesa ramentacea Species Primulaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO7760 Macrolepiota neomastoidea Species Agaricaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO295 Kokoona reflexa Species Celastraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO2250 Hylocomium splendens Species Hylocomiaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO15487 Gymnopus confluens Species Omphalotaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO422 Euphorbia cornigera Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO849 Euonymus tingens Species Celastraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO7007 Eucalyptus jenseni Species Myrtaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO7449 Eleutherobia albiflora Species Alcyoniidae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO6231 Cortinarius odoratus Species Cortinariaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO1242 Balanops australiana Species Balanopaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO17593 Pinus sylvestris Species Pinaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO4564 Anguilla japonica Species Anguillidae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO6836 Alpinia blepharocalyx Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO4564 Anguilla japonica Species Anguillidae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO2408 Millettia laurentii Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO24089 Alcea rosea Species Malvaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO6836 Alpinia blepharocalyx Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO17593 Pinus sylvestris Species Pinaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO17593 Pinus sylvestris Species Pinaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO24089 Alcea rosea Species Malvaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO2408 Millettia laurentii Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO422 Euphorbia cornigera Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18993 Araiostegiella perdurans Species Davalliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5975 Aspergillus carneus Species Aspergillaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3261 Aplysina archeri Species Aplysinidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO295 Kokoona reflexa Species Celastraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2250 Hylocomium splendens Species Hylocomiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5261 Sideroxylon cubense Species Sapotaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7007 Eucalyptus jenseni Species Myrtaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7606 Salacia lehmbachii Species Celastraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3956 Maesa ramentacea Species Primulaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6231 Cortinarius odoratus Species Cortinariaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2993 Nototodarus sloanii Species Ommastrephidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14054 Penicillium janczewskii Species Aspergillaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17593 Pinus sylvestris Species Pinaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2697 Monodora tenuifolia Species Annonaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11747 Ocimum tenuiflorum Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO849 Euonymus tingens Species Celastraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1242 Balanops australiana Species Balanopaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1489 Pseudoplexaura flagellosa Species Plexauridae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3408 Viguiera decurrens Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4274 Alcyonium utinomii Species Alcyoniidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6457 Pinus strobus Species Pinaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7760 Macrolepiota neomastoidea Species Agaricaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4564 Anguilla japonica Species Anguillidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3554 Aonidiella aurantii Species Diaspididae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24089 Alcea rosea Species Malvaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15487 Gymnopus confluens Species Omphalotaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6836 Alpinia blepharocalyx Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5584 Aldisa sanguinea Species Dorididae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25760 Aspergillus striatus Species Aspergillaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1390 Melolontha melolontha Species Scarabaeidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8058 Pluchea odorata Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7449 Eleutherobia albiflora Species Alcyoniidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3743 Sideritis brevibracteata Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4949 Salvia yosgadensis Species Lamiaceae 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

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
NPT2679 Cell line LLC-MK2 Macaca mulatta CC50 = 251500.0 nM PMID[22440015]
NPT580 Organism Trypanosoma cruzi Trypanosoma cruzi IC50 = 854000.0 nM PMID[22440015]
NPT580 Organism Trypanosoma cruzi Trypanosoma cruzi EC50 = 1630000.0 nM PMID[22440015]
NPT580 Organism Trypanosoma cruzi Trypanosoma cruzi IC50 = 18600.0 nM PMID[22440015]
NPT580 Organism Trypanosoma cruzi Trypanosoma cruzi Activity = 25.0 % PMID[22440015]
NPT580 Organism Trypanosoma cruzi Trypanosoma cruzi Activity = 91.66 % PMID[22440015]
NPT580 Organism Trypanosoma cruzi Trypanosoma cruzi Activity = 3.85 % PMID[22440015]
NPT580 Organism Trypanosoma cruzi Trypanosoma cruzi Activity = 0.71 % PMID[22440015]
NPT580 Organism Trypanosoma cruzi Trypanosoma cruzi Activity = 3.78 % PMID[22440015]
NPT580 Organism Trypanosoma cruzi Trypanosoma cruzi Activity = 1.02 % PMID[22440015]
NPT580 Organism Trypanosoma cruzi Trypanosoma cruzi Activity = 0.21 % PMID[22440015]
NPT580 Organism Trypanosoma cruzi Trypanosoma cruzi Activity = 97.96 % PMID[22440015]
NPT580 Organism Trypanosoma cruzi Trypanosoma cruzi Activity = 0.81 % PMID[22440015]

In vivo activity

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





 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 NPC36616 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
0.72 Intermediate Similarity NPC72343
0.7 Intermediate Similarity NPC488498
0.7 Intermediate Similarity NPC61952
0.7 Intermediate Similarity NPC481630
0.7 Intermediate Similarity NPC603184
0.6923 Remote Similarity NPC91369
0.6863 Remote Similarity NPC198240
0.6604 Remote Similarity NPC18819
0.6604 Remote Similarity NPC46610
0.6538 Remote Similarity NPC237591
0.6538 Remote Similarity NPC3753
0.6481 Remote Similarity NPC239098
0.6415 Remote Similarity NPC59436
0.6296 Remote Similarity NPC471159
0.6296 Remote Similarity NPC123880
0.625 Remote Similarity NPC40228
0.6182 Remote Similarity NPC269543
0.6182 Remote Similarity NPC247783
0.614 Remote Similarity NPC600691
0.6038 Remote Similarity NPC290445
0.5932 Remote Similarity NPC14203
0.5932 Remote Similarity NPC229584
0.5932 Remote Similarity NPC477782
0.5862 Remote Similarity NPC232344
0.5833 Remote Similarity NPC477783
0.5741 Remote Similarity NPC99154
0.5636 Remote Similarity NPC161923
0.5636 Remote Similarity NPC183503
0.5636 Remote Similarity NPC283908
0.5636 Remote Similarity NPC103958
0.5636 Remote Similarity NPC610917
0.5397 Remote Similarity NPC46536
0.5397 Remote Similarity NPC138139
0.5397 Remote Similarity NPC603180
0.5263 Remote Similarity NPC165711
0.5263 Remote Similarity NPC109854
0.5085 Remote Similarity NPC610334

Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC36616 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
NPD

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