Natural Product: NPC209411

Natural Product IDNPC209411
Common Name
?
The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
 Picropodophyllone
IUPAC Name (5aR,8aS,9R)-9-(3,4,5-trimethoxyphenyl)-5a,6,8a,9-tetrahydro-[2]benzofuro[5,6-f][1,3]benzodioxole-5,8-dione
Synonyms
Synthetic Gene Cluster n.a.
ChEMBL Identifier CHEMBL82303
PubChem CID 3083574
Chemical Classification
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0001392] Lignans, neolignans and related compounds
      • [CHEMONTID:0001510] Lignan lactones

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 ISCQYPPCSYRZOT-MJXNMMHHSA-N
Standard InCHI InChI=1S/C22H20O8/c1-25-16-4-10(5-17(26-2)21(16)27-3)18-11-6-14-15(30-9-29-14)7-12(11)20(23)13-8-28-22(24)19(13)18/h4-7,13,18-19H,8-9H2,1-3H3/t13-,18+,19+/m0/s1
SMILES COc1cc(cc(c1OC)OC)[C@@H]1c2cc3c(cc2C(=O)[C@H]2COC(=O)[C@@H]12)OCO3

  Calculated Properties

Physi-Chem Properties

Molecular Weight:   412.12 Volume:   395.516
?
Van der Waals volume.
Dense:   1.042 LogP:   2.01
?
The logarithm of the n-octanol/water distribution coefficients.
logD7.4:   2.332
?
The logarithm of the n-octanol/water distribution coefficient at pH=7.4.
 LogS:   -4.703
?
The logarithm of aqueous solubility value.
Rotatable Bonds:   4.0 Rigid Bonds:   27.0
TPSA:   89.52
?
Topological Polar Surface Area.
 H-Bond Acceptor:   8.0
H-Bond Donor:   0.0 Rings:   5.0
Heavy Atoms:   8.0

MedChem Properties

QED Drug-Likeness Score:   0.708 GASA:   0.0
?
GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:   3.622 Fsp3:   0.364
MCE-18:   93.333
?
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:   Accepted
Golden Triangle Rule:   Rejected BMS Rule:   0
Chelating Alert:   0 PAINS Alert:   0
Colloidal aggregators:   0.143 Fluc inhibitor:   0.093
?
The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:   0.251
?
The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1
 Green fluorescence:   0.317
?
The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:   0.246 Promiscuous compounds:   0.444

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:   -4.852 MDCK Permeability:   -4.719
Pgp-inhibitor:   0.029 Pgp-substrate:   0.0
PAMPA:   0.163
?
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):   0.0
20% Bioavailability (F20%):   0.003 30% Bioavailability (F30%):   0.0
50% Bioavailability (F50%):   0.021

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):   0.977 MRP1:   0.997
Plasma Protein Binding (PPB):   93.63% Volume Distribution (VD):   -0.034
Fu: 6.479%
?
The fraction unbound in plasms.
 OATP1B1 inhibitor:   0.227
OATP1B3 inhibitor:   0.618 BCRP inhibitor:   0.0
BSEP inhibitor:   0.998

ADMET: Metabolism

CYP1A2-inhibitor:   0.994 CYP1A2-substrate:   0.027
CYP2C19-inhibitor:   1.0 CYP2C19-substrate:   0.972
CYP2C9-inhibitor:   0.0 CYP2C9-substrate:   0.0
CYP2D6-inhibitor:   0.0 CYP2D6-substrate:   0.969
CYP3A4-inhibitor:   1.0 CYP3A4-substrate:   1.0
CYP2B6-substrate:   0.0 CYP2C8-inhibitor:   0.618
HLM stability:   0.237
?
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):  2.986 Half-life (T1/2):  2.241

ADMET: Toxicity

hERG Blockers:  0.192 hERG Blockers (10um):  0.518
Human Hepatotoxicity (H-HT):  0.848 Drug-induced Liver Injury (DILI):  0.99
AMES Toxicity:  0.638 Rat Oral Acute Toxicity:  0.413
Maximum Recommended Daily Dose:  0.734 Skin Sensitization:  0.933
Carcinogencity:  0.847 Eye Corrosion:  0.0
Eye Irritation:  0.351 Respiratory Toxicity:  0.431
Drug-induced Neurotoxicity:  0.73 Ototoxicity:  0.742
Hematotoxicity:  0.919 Drug-induced Nephrotoxicity:  0.982
Genotoxicity:  0.99 RPMI-8226 Immunitoxicity:  0.451
A549 Cytotoxicity:  0.505 Hek293 Cytotoxicity:  0.517
BCF:   1.369
?
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:   3.714
?
48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:   5.796
?
48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].
 LC50FM:   4.646
?
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
NPO21891 Panax notoginseng Species Araliaceae Eukaryota Flower buds n.a. n.a. PMID[12880307]
NPO17807 Dysosma versipellis Species Berberidaceae Eukaryota Roots Panan, Zhejiang Province, China 2004-MAY PMID[17256902]
NPO17807 Dysosma versipellis Species Berberidaceae Eukaryota n.a. root n.a. PMID[17256902]
NPO21891 Panax notoginseng Species Araliaceae Eukaryota Stems n.a. n.a. PMID[17663584]
NPO21891 Panax notoginseng Species Araliaceae Eukaryota Roots n.a. n.a. PMID[18186611]
NPO26380 Tacca plantaginea Species Taccaceae Eukaryota n.a. n.a. n.a. PMID[23031596]
NPO17807 Dysosma versipellis Species Berberidaceae Eukaryota n.a. n.a. n.a. PMID[25712646]
NPO11163 Methylobacterium organophilum Species Methylobacteriaceae Bacteria n.a. n.a. n.a. PMID[26032177]
NPO21891 Panax notoginseng Species Araliaceae Eukaryota Steamed Roots n.a. n.a. PMID[26200131]
NPO10903 Sinopodophyllum hexandrum Species Berberidaceae Eukaryota n.a. n.a. n.a. PMID[26359402]
NPO20275 Juniperus sabina Species Cupressaceae Eukaryota n.a. n.a. n.a. PMID[34203980]
NPO20275 Juniperus sabina Species Cupressaceae Eukaryota n.a. n.a. n.a. PMID[37894884]
NPO11163 Methylobacterium organophilum Species Methylobacteriaceae Bacteria n.a. n.a. n.a. PMID[3928379]
NPO7946 Navicula delognei Species Berkeleyaceae Eukaryota n.a. n.a. n.a. PMID[6512534]
NPO22726 Carthamus lanatus Species Asteraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO20275 Juniperus sabina Species Cupressaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO27244 Dysosma pleiantha Species Berberidaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO18134 Heliobacterium modesticaldum Species Heliobacteriaceae Bacteria n.a. n.a. n.a. Database[COCONUT]
NPO3675 Actinobole uliginosum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO7946 Navicula delognei Species Berkeleyaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO26380 Tacca plantaginea Species Taccaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO25651 Tecoma grandiflora Species Bignoniaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO22413 Dysosma aurantiocaulis Species Berberidaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO27647 Diphylleia cymosa Species Berberidaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO23382 Podophyllum emodii Species Berberidaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO18381 Inula eupatorioides Species Asteraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO4464 Senecio mexicanus Species Asteraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO26179 Chrysosplenium tetrandrum Species Saxifragaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO3025 Schefflera capitata Species Araliaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO10903 Sinopodophyllum hexandrum Species Berberidaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO26868 Diphylleia sinensis Species Berberidaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO6893 Dimorphotheca sinuata Species Asteraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO21891 Panax notoginseng Species Araliaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO25340 Galega officinalis Species Fabaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO22413 Dysosma aurantiocaulis Species Berberidaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO17807 Dysosma versipellis Species Berberidaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO26868 Diphylleia sinensis Species Berberidaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO23382 Podophyllum emodii Species Berberidaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO27244 Dysosma pleiantha Species Berberidaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO26380 Tacca plantaginea Species Taccaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO25340 Galega officinalis Species Fabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO20275 Juniperus sabina Species Cupressaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO27647 Diphylleia cymosa Species Berberidaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO22413 Dysosma aurantiocaulis Species Berberidaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO26868 Diphylleia sinensis Species Berberidaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO7946 Navicula delognei Species Berkeleyaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO5627 Dysosma majoensis Species Berberidaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO27244 Dysosma pleiantha Species Berberidaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO26380 Tacca plantaginea Species Taccaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO17807 Dysosma versipellis Species Berberidaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO22208 Spiraea mongolica Species Rosaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO20275 Juniperus sabina Species Cupressaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO23382 Podophyllum emodii Species Berberidaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO25340 Galega officinalis Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO22208 Spiraea mongolica Species Rosaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO20275 Juniperus sabina Species Cupressaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO26868 Diphylleia sinensis Species Berberidaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO21891 Panax notoginseng Species Araliaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO17807 Dysosma versipellis Species Berberidaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO26380 Tacca plantaginea Species Taccaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO10903 Sinopodophyllum hexandrum Species Berberidaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO21891 Panax notoginseng Species Araliaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO26710 Hypotrachyna rachista Species Parmeliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3025 Schefflera capitata Species Araliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27244 Dysosma pleiantha Species Berberidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19243 Sarcophyton decaryi Species Orchidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16081 Peltophorum dasyrhachis Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22266 Fagus taurica Species Fagaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10903 Sinopodophyllum hexandrum Species Berberidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26868 Diphylleia sinensis Species Berberidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26380 Tacca plantaginea Species Taccaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22783 Pteris arguta Species Pteridaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11417 Gesneria cardinalis Species Crambidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11163 Methylobacterium organophilum Species Methylobacteriaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO6893 Dimorphotheca sinuata Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13152 Chalcas paniculata n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO3675 Actinobole uliginosum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4464 Senecio mexicanus Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21891 Panax notoginseng Species Araliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22726 Carthamus lanatus Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23767 Aspropaxillus candidus Species Tricholomataceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21763 Parmotrema subisidiosum Species Parmeliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21288 Ficus rumphii Species Moraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25340 Galega officinalis Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18134 Heliobacterium modesticaldum Species Heliobacteriaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO26179 Chrysosplenium tetrandrum Species Saxifragaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22208 Spiraea mongolica Species Rosaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21892 Eisenibacter elegans Species Microscillaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO20275 Juniperus sabina Species Cupressaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18381 Inula eupatorioides Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23074 Achillea grandifolia Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7946 Navicula delognei Species Berkeleyaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27647 Diphylleia cymosa Species Berberidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17807 Dysosma versipellis Species Berberidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22026 Sibthorpia africana Species Plantaginaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22413 Dysosma aurantiocaulis Species Berberidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25651 Tecoma grandiflora Species Bignoniaceae 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
NPT168 Cell line P388 Mus musculus IC50 = 12000.0 nM DOI[10.1016/0960-894X(95)00432-S]
NPT81 Cell line A549 Homo sapiens IC50 = 12000.0 nM DOI[10.1016/0960-894X(95)00432-S]
NPT139 Cell line HT-29 Homo sapiens IC50 = 12000.0 nM DOI[10.1016/0960-894X(95)00432-S]
NPT3885 Cell line CV-1 Chlorocebus aethiops IC50 = 48000.0 nM DOI[10.1016/0960-894X(95)00432-S]

In vivo activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT1769 Organism Mythimna separata Mythimna separata mortality = 27.6 % PMID[22891988]
NPT1769 Organism Mythimna separata Mythimna separata mortality = 20.7 % PMID[22891988]
NPT1769 Organism Mythimna separata Mythimna separata mortality = 16.7 % PMID[22891988]





 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 NPC209411 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
1.0 High Similarity NPC239890
0.6557 Remote Similarity NPC237946
0.6557 Remote Similarity NPC32373
0.65 Remote Similarity NPC80230
0.65 Remote Similarity NPC104024
0.65 Remote Similarity NPC101755
0.65 Remote Similarity NPC304687
0.65 Remote Similarity NPC65574
0.6129 Remote Similarity NPC262455
0.6129 Remote Similarity NPC177476
0.6094 Remote Similarity NPC210642
0.6094 Remote Similarity NPC13985
0.6094 Remote Similarity NPC207584
0.6094 Remote Similarity NPC19947
0.6032 Remote Similarity NPC149505
0.5909 Remote Similarity NPC119910
0.5781 Remote Similarity NPC480477
0.5588 Remote Similarity NPC115281
0.5517 Remote Similarity NPC151423
0.5362 Remote Similarity NPC288149
0.5362 Remote Similarity NPC470637
0.5345 Remote Similarity NPC218841
0.5323 Remote Similarity NPC477698
0.5294 Remote Similarity NPC91634
0.5294 Remote Similarity NPC150943
0.5294 Remote Similarity NPC268718
0.5246 Remote Similarity NPC86455
0.5246 Remote Similarity NPC125134
0.5246 Remote Similarity NPC137920
0.5167 Remote Similarity NPC475000
0.5161 Remote Similarity NPC164082
0.5147 Remote Similarity NPC30009
0.5147 Remote Similarity NPC103197
0.5077 Remote Similarity NPC218092
0.5077 Remote Similarity NPC246474
0.5077 Remote Similarity NPC162851

Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC209411 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
0.6557 Remote Similarity NPD4965 Approved
0.6557 Remote Similarity NPD4966 Phase 4
0.6557 Remote Similarity NPD4967 Phase 2
0.5455 Remote Similarity NPD37 Approved

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