Structure

Physi-Chem Properties

Molecular Weight:  212.08
Volume:  232.713
LogP:  2.927
LogD:  3.485
LogS:  -3.009
# Rotatable Bonds:  2
TPSA:  40.46
# H-Bond Aceptor:  2
# H-Bond Donor:  2
# Rings:  2
# Heavy Atoms:  2

MedChem Properties

QED Drug-Likeness Score:  0.75
Synthetic Accessibility Score:  1.944
Fsp3:  0.0
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Accepted
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.887
MDCK Permeability:  1.3355581359064672e-05
Pgp-inhibitor:  0.087
Pgp-substrate:  0.001
Human Intestinal Absorption (HIA):  0.033
20% Bioavailability (F20%):  0.981
30% Bioavailability (F30%):  0.955

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.052
Plasma Protein Binding (PPB):  97.13024139404297%
Volume Distribution (VD):  0.847
Pgp-substrate:  2.667802333831787%

ADMET: Metabolism

CYP1A2-inhibitor:  0.993
CYP1A2-substrate:  0.096
CYP2C19-inhibitor:  0.485
CYP2C19-substrate:  0.059
CYP2C9-inhibitor:  0.33
CYP2C9-substrate:  0.935
CYP2D6-inhibitor:  0.716
CYP2D6-substrate:  0.717
CYP3A4-inhibitor:  0.943
CYP3A4-substrate:  0.14

ADMET: Excretion

Clearance (CL):  12.959
Half-life (T1/2):  0.898

ADMET: Toxicity

hERG Blockers:  0.136
Human Hepatotoxicity (H-HT):  0.065
Drug-inuced Liver Injury (DILI):  0.108
AMES Toxicity:  0.067
Rat Oral Acute Toxicity:  0.041
Maximum Recommended Daily Dose:  0.459
Skin Sensitization:  0.945
Carcinogencity:  0.246
Eye Corrosion:  0.506
Eye Irritation:  0.991
Respiratory Toxicity:  0.445

Download Data

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General Info & Identifiers & Properties  
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Biological Activities  
Similar NPs/Drugs  

  Natural Product: NPC291789

Natural Product ID:  NPC291789
Common Name*:   Pinosylvin
IUPAC Name:   5-[(E)-2-phenylethenyl]benzene-1,3-diol
Synonyms:   Pinosylvin
Standard InCHIKey:  YCVPRTHEGLPYPB-VOTSOKGWSA-N
Standard InCHI:  InChI=1S/C14H12O2/c15-13-8-12(9-14(16)10-13)7-6-11-4-2-1-3-5-11/h1-10,15-16H/b7-6+
SMILES:  c1ccc(cc1)/C=C/c1cc(cc(c1)O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL101506
PubChem CID:   5280457
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000261] Phenylpropanoids and polyketides
      • [CHEMONTID:0000253] Stilbenes

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

  Species Source

Organism ID Organism Name Taxonomy Level Family SuperKingdom Isolation Part Collection Location Collection Time Reference
NPO5638 Garcinia livingstonei Species Clusiaceae Eukaryota n.a. fruit n.a. DOI[10.1016/S0040-4020(01)89039-6]
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]
NPO30254 Stemona collinsae Species Stemonaceae Eukaryota Leaves, rhizomes, and roots southeast Thailand near Chonburi 2000-Feb, 2001-Jan PMID[12088422]
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]
NPO4703 Solanum hispidum Species Solanaceae Eukaryota leaves n.a. n.a. PMID[15217270]
NPO32936 calligonum leucocladum Species Polygonaceae Eukaryota n.a. n.a. n.a. PMID[15217293]
NPO17593 Pinus sylvestris Species Pinaceae Eukaryota n.a. n.a. n.a. PMID[1536925]
NPO30254 Stemona collinsae Species Stemonaceae Eukaryota n.a. n.a. n.a. PMID[15679323]
NPO30254 Stemona collinsae Species Stemonaceae Eukaryota n.a. Southeast Thailand near Chonburi, Khao Khieo, close to the Chanthathen waterfall and Sri Racha n.a. PMID[15679323]
NPO30254 Stemona collinsae Species Stemonaceae Eukaryota slowly dried tubers Bangkok, Thailand n.a. PMID[15679323]
NPO46 Onosma hispida Species Boraginaceae Eukaryota n.a. whole plant n.a. PMID[16079517]
NPO14054 Penicillium janczewskii Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[16180822]
NPO5638 Garcinia livingstonei Species Clusiaceae Eukaryota root bark n.a. n.a. PMID[16562837]
NPO422 Euphorbia cornigera Species Euphorbiaceae Eukaryota n.a. n.a. n.a. PMID[17512094]
NPO1830 Dalbergia sissoo Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[18154272]
NPO422 Euphorbia cornigera Species Euphorbiaceae Eukaryota n.a. n.a. n.a. PMID[19376614]
NPO28574 Oroxylum indicum Species Bignoniaceae Eukaryota n.a. n.a. n.a. PMID[19948405]
NPO5638 Garcinia livingstonei Species Clusiaceae Eukaryota n.a. fruit n.a. PMID[21028890]
NPO19780 Stemona sessilifolia Species Stemonaceae Eukaryota n.a. root n.a. PMID[21902195]
NPO1830 Dalbergia sissoo Species Fabaceae Eukaryota leaves n.a. n.a. PMID[22212722]
NPO28574 Oroxylum indicum Species Bignoniaceae Eukaryota n.a. seed n.a. PMID[23672042]
NPO17593 Pinus sylvestris Species Pinaceae Eukaryota n.a. seed n.a. PMID[24225786]
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]
NPO14359 Pentarhizidium orientale Species Onocleaceae Eukaryota Rhizomes n.a. n.a. PMID[28984452]
NPO2697 Monodora tenuifolia Species Annonaceae Eukaryota n.a. n.a. n.a. PMID[3509958]
NPO6836 Alpinia blepharocalyx Species Zingiberaceae Eukaryota n.a. n.a. n.a. PMID[9461664]
NPO4564 Anguilla japonica Species Anguillidae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO19780 Stemona sessilifolia Species Stemonaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO31022 0thofagus sp Species 0thofagaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO28574 Oroxylum indicum Species Bignoniaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO31087 Pinus sp Species Pinaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO16850 Eucommia ulmoides Species Eucommiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO10525 Alnus sieboldiana Species Betulaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO1830 Dalbergia sissoo Species Fabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO17593 Pinus sylvestris Species Pinaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO12104 Stemona cf. pierrei Species Stemonaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO46 Onosma hispida Species Boraginaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO6836 Alpinia blepharocalyx Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO28574 Oroxylum indicum Species Bignoniaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO2511 0thofagus sp. Species 0thofagaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO4564 Anguilla japonica Species Anguillidae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO17593 Pinus sylvestris Species Pinaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO14359 Pentarhizidium orientale Species Onocleaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO12104 Stemona cf. pierrei Species Stemonaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO46 Onosma hispida Species Boraginaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO6836 Alpinia blepharocalyx Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO12624 Pinus sp. Species Pinaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO1830 Dalbergia sissoo Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO10525 Alnus sieboldiana Species Betulaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO16850 Eucommia ulmoides Species Eucommiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO19780 Stemona sessilifolia Species Stemonaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO24089 Alcea rosea Species Malvaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO2408 Millettia laurentii Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO19780 Stemona sessilifolia Species Stemonaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO1830 Dalbergia sissoo Species Fabaceae 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]
NPO17593 Pinus sylvestris Species Pinaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO28574 Oroxylum indicum Species Bignoniaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO30254 Stemona collinsae Species Stemonaceae Eukaryota leaf and root n.a. n.a. Database[Title]
NPO16850 Eucommia ulmoides Species Eucommiaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO28574 Oroxylum indicum Species Bignoniaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO24089 Alcea rosea Species Malvaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO10525 Alnus sieboldiana Species Betulaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25760 Aspergillus striatus Species Aspergillaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5638 Garcinia livingstonei Species Clusiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7606 Salacia lehmbachii Species Celastraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4274 Alcyonium utinomii Species Alcyoniidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5584 Aldisa sanguinea Species Dorididae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27945 Cancrinia discoidea Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7007 Eucalyptus jenseni Species Myrtaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3408 Viguiera decurrens Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5261 Sideroxylon cubense Species Sapotaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16850 Eucommia ulmoides Species Eucommiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1896 Proteus penneri Species Morganellaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO2250 Hylocomium splendens Species Hylocomiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO422 Euphorbia cornigera Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6836 Alpinia blepharocalyx Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO295 Kokoona reflexa Species Celastraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1489 Pseudoplexaura flagellosa Species Plexauridae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO849 Euonymus tingens Species Celastraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO46 Onosma hispida Species Boraginaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4703 Solanum hispidum Species Solanaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3261 Aplysina archeri Species Aplysinidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11747 Ocimum tenuiflorum Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1242 Balanops australiana Species Balanopaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5975 Aspergillus carneus Species Aspergillaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2697 Monodora tenuifolia Species Annonaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24089 Alcea rosea Species Malvaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18993 Araiostegiella perdurans Species Davalliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28574 Oroxylum indicum Species Bignoniaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2408 Millettia laurentii Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3554 Aonidiella aurantii Species Diaspididae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3789 Lyonia formosa Species Ericaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15487 Gymnopus confluens Species Omphalotaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19780 Stemona sessilifolia Species Stemonaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4949 Salvia yosgadensis Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17593 Pinus sylvestris Species Pinaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4564 Anguilla japonica Species Anguillidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1830 Dalbergia sissoo Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3743 Sideritis brevibracteata Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14054 Penicillium janczewskii Species Aspergillaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7760 Macrolepiota neomastoidea Species Agaricaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7449 Eleutherobia albiflora Species Alcyoniidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2993 0totodarus sloanii Species Ommastrephidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14359 Pentarhizidium orientale Species Onocleaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8058 Pluchea odorata Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6231 Cortinarius odoratus Species Cortinariaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6457 Pinus strobus Species Pinaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2828 Blaps mucronata Species Tenebrionidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1390 Melolontha melolontha Species Scarabaeidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3956 Maesa ramentacea Species Primulaceae 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 NP ID 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

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT13 Individual Protein Tyrosine-protein kinase LCK Homo sapiens IC50 = 193000.0 nM PMID[491645]
NPT113 Cell Line RAW264.7 Mus musculus IC50 = 10600.0 nM PMID[491646]
NPT116 Cell Line HL-60 Homo sapiens Activity = 36.95 % PMID[491649]
NPT365 Individual Protein NAD(P)H dehydrogenase [quinone] 1 Mus musculus Activity > 20.0 uM PMID[491652]
NPT472 Individual Protein Vanilloid receptor Homo sapiens IC50 > 10000.0 nM PMID[491657]
NPT472 Individual Protein Vanilloid receptor Homo sapiens Efficacy < 10.0 % PMID[491657]
NPT1534 Individual Protein Transient receptor potential cation channel subfamily A member 1 Rattus norvegicus Efficacy < 10.0 % PMID[491657]
NPT1534 Individual Protein Transient receptor potential cation channel subfamily A member 1 Rattus norvegicus IC50 = 12100.0 nM PMID[491657]
NPT346 Individual Protein Transient receptor potential cation channel subfamily A member 1 Homo sapiens FC = -0.1 n.a. PMID[491659]
NPT346 Individual Protein Transient receptor potential cation channel subfamily A member 1 Homo sapiens FC = 0.4 n.a. PMID[491659]
NPT1886 Cell Line J774 Mus musculus IC50 = 16600.0 nM PMID[491660]
NPT1886 Cell Line J774 Mus musculus IC50 = 32100.0 nM PMID[491660]
NPT1886 Cell Line J774 Mus musculus IC50 = 38700.0 nM PMID[491660]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. Activity = 2.04 n.a. PMID[491647]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. Activity = 61.0 % PMID[491647]
NPT2 Others Unspecified Activity = 1.07 uM PMID[491647]
NPT35 Others n.a. Ratio = 0.52 n.a. PMID[491648]
NPT16 Organism Staphylococcus aureus Staphylococcus aureus MIC > 250.0 ug.mL-1 PMID[491648]
NPT16 Organism Staphylococcus aureus Staphylococcus aureus MIC = 125.0 ug.mL-1 PMID[491648]
NPT2 Others Unspecified IC50 = 22700.0 nM PMID[491651]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. IC50 > 25000.0 nM PMID[491652]
NPT35 Others n.a. LogP = 2.25 n.a. PMID[491654]
NPT35 Others n.a. INH = 3.3 10'5L/mol/s PMID[491655]
NPT35 Others n.a. TIME = 0.3617 hr PMID[491655]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. TIME = 0.7167 hr PMID[491655]
NPT35 Others n.a. Time = 2.4 10'3s PMID[491655]
NPT35 Others n.a. INH = 0.5 10'4L/mol/s PMID[491655]
NPT35 Others n.a. Time = 1.5 10'3s PMID[491655]
NPT35 Others n.a. INH = 1.7 10'4L/mol/s PMID[491655]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. TIME = 2.3 hr PMID[491655]
NPT1 Others Radical scavenging activity Inhibition = 29.8 % PMID[491655]
NPT72 Individual Protein Solute carrier organic anion transporter family member 1B3 Homo sapiens Inhibition = 114.57 % PMID[491656]
NPT73 Individual Protein Solute carrier organic anion transporter family member 1B1 Homo sapiens Inhibition = 133.48 % PMID[491656]

☑ Note for Activity Records:
☉ The quantitative biological activities were primarily integrated from ChEMBL (Version-30) database and were also directly collected from PubMed literature. PubMed PMID was provided as the reference link for each activity record.

  Chemically structural similarity: I. Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes 4,3285 NPs with experimentally-derived bioactivity available in NPASS)

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules. Tc lies between [0, 1] where '1' indicates the highest similarity. What is Tanimoto coefficient

●  The left chart: Distribution of similarity level between NPC291789 and all remaining natural products in the NPASS database.
●  The right table: Most similar natural products (Tc>=0.56 or Top200).

Similarity Score Similarity Level Natural Product ID
0.9785 High Similarity NPC161571
0.9785 High Similarity NPC248573
0.9785 High Similarity NPC275053
0.9681 High Similarity NPC100340
0.9681 High Similarity NPC143659
0.9479 High Similarity NPC30506
0.9479 High Similarity NPC241891
0.9479 High Similarity NPC102216
0.9381 High Similarity NPC292452
0.9381 High Similarity NPC134829
0.9348 High Similarity NPC295295
0.9286 High Similarity NPC470700
0.9286 High Similarity NPC302681
0.9286 High Similarity NPC39097
0.9286 High Similarity NPC39664
0.9286 High Similarity NPC109691
0.9286 High Similarity NPC118286
0.9192 High Similarity NPC176527
0.9192 High Similarity NPC54844
0.9184 High Similarity NPC246056
0.9167 High Similarity NPC10588
0.9167 High Similarity NPC166761
0.91 High Similarity NPC114392
0.91 High Similarity NPC174981
0.91 High Similarity NPC58427
0.91 High Similarity NPC34864
0.91 High Similarity NPC105727
0.9072 High Similarity NPC284011
0.9072 High Similarity NPC72947
0.901 High Similarity NPC19808
0.901 High Similarity NPC33728
0.901 High Similarity NPC202647
0.898 High Similarity NPC71002
0.898 High Similarity NPC302219
0.898 High Similarity NPC146798
0.898 High Similarity NPC106396
0.898 High Similarity NPC313030
0.898 High Similarity NPC249828
0.898 High Similarity NPC94351
0.898 High Similarity NPC222522
0.898 High Similarity NPC85479
0.898 High Similarity NPC24404
0.898 High Similarity NPC53051
0.898 High Similarity NPC168303
0.898 High Similarity NPC242342
0.8922 High Similarity NPC94045
0.89 High Similarity NPC248904
0.8889 High Similarity NPC119860
0.8878 High Similarity NPC11280
0.8878 High Similarity NPC294186
0.8878 High Similarity NPC166313
0.8878 High Similarity NPC24407
0.8878 High Similarity NPC147310
0.8878 High Similarity NPC137415
0.8878 High Similarity NPC192032
0.8835 High Similarity NPC476632
0.8835 High Similarity NPC4493
0.8835 High Similarity NPC165770
0.8835 High Similarity NPC224527
0.8835 High Similarity NPC225679
0.8835 High Similarity NPC268032
0.8835 High Similarity NPC90520
0.8835 High Similarity NPC296920
0.88 High Similarity NPC474839
0.8788 High Similarity NPC168393
0.875 High Similarity NPC166995
0.875 High Similarity NPC274678
0.875 High Similarity NPC280606
0.875 High Similarity NPC43525
0.87 High Similarity NPC227458
0.87 High Similarity NPC218879
0.87 High Similarity NPC244513
0.8673 High Similarity NPC80027
0.8667 High Similarity NPC117846
0.8667 High Similarity NPC261343
0.8654 High Similarity NPC255068
0.8646 High Similarity NPC76938
0.8627 High Similarity NPC204901
0.8627 High Similarity NPC232523
0.8627 High Similarity NPC305603
0.8627 High Similarity NPC61033
0.8627 High Similarity NPC158253
0.8614 High Similarity NPC37802
0.8587 High Similarity NPC150837
0.8585 High Similarity NPC22610
0.8585 High Similarity NPC228287
0.8585 High Similarity NPC180508
0.8585 High Similarity NPC107240
0.8585 High Similarity NPC276737
0.8557 High Similarity NPC32714
0.8544 High Similarity NPC63698
0.8544 High Similarity NPC61885
0.8529 High Similarity NPC12640
0.8529 High Similarity NPC164576
0.8529 High Similarity NPC99836
0.8529 High Similarity NPC67250
0.8529 High Similarity NPC201662
0.8511 High Similarity NPC27974
0.8505 High Similarity NPC167934
0.8505 High Similarity NPC84999
0.8505 High Similarity NPC808
0.8505 High Similarity NPC53906
0.8505 High Similarity NPC246760
0.8491 Intermediate Similarity NPC23804
0.8462 Intermediate Similarity NPC186385
0.8462 Intermediate Similarity NPC299568
0.8438 Intermediate Similarity NPC45040
0.8426 Intermediate Similarity NPC150624
0.8426 Intermediate Similarity NPC141090
0.8426 Intermediate Similarity NPC203113
0.84 Intermediate Similarity NPC223393
0.84 Intermediate Similarity NPC294741
0.8384 Intermediate Similarity NPC32674
0.8384 Intermediate Similarity NPC156313
0.8381 Intermediate Similarity NPC242178
0.8381 Intermediate Similarity NPC475018
0.8352 Intermediate Similarity NPC270094
0.8349 Intermediate Similarity NPC470759
0.8349 Intermediate Similarity NPC474933
0.8349 Intermediate Similarity NPC69261
0.8349 Intermediate Similarity NPC219070
0.8349 Intermediate Similarity NPC15860
0.8349 Intermediate Similarity NPC50521
0.8349 Intermediate Similarity NPC195466
0.8349 Intermediate Similarity NPC221549
0.8349 Intermediate Similarity NPC33270
0.8349 Intermediate Similarity NPC127894
0.8349 Intermediate Similarity NPC244816
0.8349 Intermediate Similarity NPC470760
0.8333 Intermediate Similarity NPC192
0.8333 Intermediate Similarity NPC312304
0.8333 Intermediate Similarity NPC472893
0.8317 Intermediate Similarity NPC12221
0.8316 Intermediate Similarity NPC19680
0.8283 Intermediate Similarity NPC132271
0.8283 Intermediate Similarity NPC82664
0.8283 Intermediate Similarity NPC216520
0.8283 Intermediate Similarity NPC292730
0.828 Intermediate Similarity NPC265146
0.8273 Intermediate Similarity NPC190514
0.8273 Intermediate Similarity NPC144343
0.8269 Intermediate Similarity NPC35543
0.8265 Intermediate Similarity NPC151715
0.8265 Intermediate Similarity NPC128062
0.8257 Intermediate Similarity NPC114064
0.8257 Intermediate Similarity NPC115808
0.8252 Intermediate Similarity NPC471350
0.8247 Intermediate Similarity NPC231150
0.8242 Intermediate Similarity NPC4154
0.8241 Intermediate Similarity NPC249270
0.8235 Intermediate Similarity NPC233827
0.8218 Intermediate Similarity NPC130103
0.8208 Intermediate Similarity NPC168657
0.8208 Intermediate Similarity NPC224870
0.82 Intermediate Similarity NPC88420
0.8198 Intermediate Similarity NPC217174
0.8198 Intermediate Similarity NPC226629
0.8198 Intermediate Similarity NPC184302
0.8191 Intermediate Similarity NPC175313
0.8191 Intermediate Similarity NPC248817
0.819 Intermediate Similarity NPC169450
0.819 Intermediate Similarity NPC245115
0.819 Intermediate Similarity NPC95344
0.8182 Intermediate Similarity NPC257182
0.8182 Intermediate Similarity NPC277588
0.8182 Intermediate Similarity NPC26244
0.8163 Intermediate Similarity NPC29373
0.8163 Intermediate Similarity NPC271440
0.8163 Intermediate Similarity NPC3358
0.8163 Intermediate Similarity NPC94139
0.8163 Intermediate Similarity NPC210497
0.8163 Intermediate Similarity NPC147284
0.8163 Intermediate Similarity NPC55903
0.8163 Intermediate Similarity NPC162314
0.8163 Intermediate Similarity NPC306884
0.8155 Intermediate Similarity NPC323810
0.8155 Intermediate Similarity NPC471511
0.8155 Intermediate Similarity NPC474603
0.8155 Intermediate Similarity NPC12987
0.8148 Intermediate Similarity NPC319803
0.8144 Intermediate Similarity NPC47950
0.8144 Intermediate Similarity NPC300478
0.8125 Intermediate Similarity NPC61516
0.8125 Intermediate Similarity NPC223451
0.8125 Intermediate Similarity NPC474565
0.8125 Intermediate Similarity NPC247364
0.8125 Intermediate Similarity NPC10932
0.8125 Intermediate Similarity NPC104216
0.8125 Intermediate Similarity NPC472071
0.8125 Intermediate Similarity NPC232084
0.8125 Intermediate Similarity NPC69006
0.8119 Intermediate Similarity NPC92730
0.8113 Intermediate Similarity NPC82016
0.8108 Intermediate Similarity NPC48781
0.8108 Intermediate Similarity NPC9592
0.8105 Intermediate Similarity NPC155393
0.8105 Intermediate Similarity NPC197783
0.81 Intermediate Similarity NPC473388
0.8085 Intermediate Similarity NPC124436
0.8081 Intermediate Similarity NPC245187

  Chemically structural similarity: II. Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC291789 and all drugs/candidates.
●  The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

Similarity Score Similarity Level Drug ID Developmental Stage
0.9785 High Similarity NPD1242 Phase 1
0.85 High Similarity NPD940 Approved
0.85 High Similarity NPD846 Approved
0.8462 Intermediate Similarity NPD4750 Phase 3
0.8352 Intermediate Similarity NPD9089 Approved
0.8265 Intermediate Similarity NPD2934 Approved
0.8265 Intermediate Similarity NPD2933 Approved
0.8242 Intermediate Similarity NPD9093 Approved
0.8182 Intermediate Similarity NPD2859 Approved
0.8182 Intermediate Similarity NPD2860 Approved
0.8119 Intermediate Similarity NPD3020 Approved
0.8085 Intermediate Similarity NPD111 Approved
0.8 Intermediate Similarity NPD844 Approved
0.7921 Intermediate Similarity NPD288 Approved
0.7864 Intermediate Similarity NPD289 Clinical (unspecified phase)
0.7835 Intermediate Similarity NPD9094 Approved
0.7788 Intermediate Similarity NPD1548 Phase 1
0.7778 Intermediate Similarity NPD3022 Approved
0.7778 Intermediate Similarity NPD3021 Approved
0.7723 Intermediate Similarity NPD1432 Clinical (unspecified phase)
0.7672 Intermediate Similarity NPD1610 Phase 2
0.7593 Intermediate Similarity NPD2342 Discontinued
0.7521 Intermediate Similarity NPD1529 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD9273 Approved
0.75 Intermediate Similarity NPD968 Approved
0.7473 Intermediate Similarity NPD9087 Approved
0.7459 Intermediate Similarity NPD3027 Phase 3
0.7459 Intermediate Similarity NPD4625 Phase 3
0.7455 Intermediate Similarity NPD1792 Phase 2
0.7451 Intermediate Similarity NPD845 Approved
0.7438 Intermediate Similarity NPD1530 Clinical (unspecified phase)
0.7411 Intermediate Similarity NPD7635 Approved
0.7395 Intermediate Similarity NPD4749 Approved
0.7383 Intermediate Similarity NPD9500 Approved
0.734 Intermediate Similarity NPD9088 Approved
0.7339 Intermediate Similarity NPD1445 Approved
0.7339 Intermediate Similarity NPD1444 Approved
0.7281 Intermediate Similarity NPD1476 Clinical (unspecified phase)
0.728 Intermediate Similarity NPD1613 Approved
0.728 Intermediate Similarity NPD1612 Clinical (unspecified phase)
0.728 Intermediate Similarity NPD943 Approved
0.725 Intermediate Similarity NPD2983 Phase 2
0.725 Intermediate Similarity NPD2982 Phase 2
0.7236 Intermediate Similarity NPD4908 Phase 1
0.7232 Intermediate Similarity NPD9280 Clinical (unspecified phase)
0.7227 Intermediate Similarity NPD422 Phase 1
0.7227 Intermediate Similarity NPD1201 Approved
0.7196 Intermediate Similarity NPD3028 Approved
0.7168 Intermediate Similarity NPD228 Approved
0.7167 Intermediate Similarity NPD2981 Phase 2
0.7165 Intermediate Similarity NPD2568 Approved
0.7143 Intermediate Similarity NPD1809 Phase 2
0.7143 Intermediate Similarity NPD9380 Clinical (unspecified phase)
0.712 Intermediate Similarity NPD4907 Clinical (unspecified phase)
0.7105 Intermediate Similarity NPD9379 Approved
0.7105 Intermediate Similarity NPD9377 Approved
0.7073 Intermediate Similarity NPD859 Approved
0.7073 Intermediate Similarity NPD602 Approved
0.7073 Intermediate Similarity NPD858 Approved
0.7073 Intermediate Similarity NPD599 Approved
0.7073 Intermediate Similarity NPD6917 Clinical (unspecified phase)
0.7069 Intermediate Similarity NPD6671 Approved
0.7059 Intermediate Similarity NPD2286 Discontinued
0.7053 Intermediate Similarity NPD9294 Approved
0.7043 Intermediate Similarity NPD2229 Approved
0.7043 Intermediate Similarity NPD2228 Approved
0.7043 Intermediate Similarity NPD2234 Approved
0.7034 Intermediate Similarity NPD3091 Approved
0.7025 Intermediate Similarity NPD9269 Phase 2
0.7016 Intermediate Similarity NPD3018 Phase 2
0.7 Intermediate Similarity NPD9610 Approved
0.7 Intermediate Similarity NPD9608 Approved
0.6992 Remote Similarity NPD4339 Clinical (unspecified phase)
0.6992 Remote Similarity NPD1470 Approved
0.6984 Remote Similarity NPD6410 Clinical (unspecified phase)
0.6983 Remote Similarity NPD9618 Approved
0.6983 Remote Similarity NPD9614 Approved
0.6975 Remote Similarity NPD9268 Approved
0.6975 Remote Similarity NPD4093 Discontinued
0.6964 Remote Similarity NPD9265 Clinical (unspecified phase)
0.6942 Remote Similarity NPD3092 Approved
0.6923 Remote Similarity NPD1509 Clinical (unspecified phase)
0.6923 Remote Similarity NPD709 Approved
0.6917 Remote Similarity NPD4059 Approved
0.6917 Remote Similarity NPD9384 Approved
0.6917 Remote Similarity NPD2932 Approved
0.6917 Remote Similarity NPD5238 Clinical (unspecified phase)
0.6917 Remote Similarity NPD9381 Approved
0.6917 Remote Similarity NPD3019 Approved
0.6903 Remote Similarity NPD9266 Approved
0.6903 Remote Similarity NPD74 Approved
0.6891 Remote Similarity NPD2226 Clinical (unspecified phase)
0.6885 Remote Similarity NPD1608 Approved
0.6885 Remote Similarity NPD2337 Clinical (unspecified phase)
0.688 Remote Similarity NPD2861 Phase 2
0.6875 Remote Similarity NPD1240 Approved
0.6875 Remote Similarity NPD1555 Discontinued
0.6864 Remote Similarity NPD405 Clinical (unspecified phase)
0.686 Remote Similarity NPD1981 Approved
0.686 Remote Similarity NPD1980 Approved
0.686 Remote Similarity NPD1983 Approved
0.6855 Remote Similarity NPD3094 Phase 2
0.6838 Remote Similarity NPD1791 Approved
0.6838 Remote Similarity NPD1793 Approved
0.6838 Remote Similarity NPD497 Approved
0.6829 Remote Similarity NPD4379 Clinical (unspecified phase)
0.6829 Remote Similarity NPD3600 Clinical (unspecified phase)
0.6814 Remote Similarity NPD290 Approved
0.6814 Remote Similarity NPD9263 Approved
0.6814 Remote Similarity NPD9264 Approved
0.6814 Remote Similarity NPD9267 Approved
0.6807 Remote Similarity NPD9613 Approved
0.6807 Remote Similarity NPD9615 Approved
0.6807 Remote Similarity NPD9616 Approved
0.6803 Remote Similarity NPD5350 Clinical (unspecified phase)
0.6803 Remote Similarity NPD5351 Clinical (unspecified phase)
0.6794 Remote Similarity NPD1510 Phase 2
0.6777 Remote Similarity NPD1751 Approved
0.6774 Remote Similarity NPD5310 Approved
0.6774 Remote Similarity NPD5311 Approved
0.6769 Remote Similarity NPD1607 Approved
0.6752 Remote Similarity NPD495 Approved
0.6752 Remote Similarity NPD496 Approved
0.6752 Remote Similarity NPD5283 Phase 1
0.6752 Remote Similarity NPD498 Approved
0.675 Remote Similarity NPD316 Approved
0.6748 Remote Similarity NPD2561 Approved
0.6748 Remote Similarity NPD2562 Approved
0.6742 Remote Similarity NPD6100 Approved
0.6742 Remote Similarity NPD6099 Approved
0.6742 Remote Similarity NPD1551 Phase 2
0.6731 Remote Similarity NPD9295 Approved
0.6723 Remote Similarity NPD9493 Approved
0.672 Remote Similarity NPD1164 Approved
0.672 Remote Similarity NPD3053 Approved
0.672 Remote Similarity NPD3055 Approved
0.6719 Remote Similarity NPD6859 Clinical (unspecified phase)
0.6696 Remote Similarity NPD9244 Approved
0.6694 Remote Similarity NPD4659 Approved
0.6694 Remote Similarity NPD9622 Approved
0.6692 Remote Similarity NPD230 Phase 1
0.6667 Remote Similarity NPD6405 Approved
0.6667 Remote Similarity NPD6407 Approved
0.6667 Remote Similarity NPD317 Approved
0.6667 Remote Similarity NPD318 Approved
0.6667 Remote Similarity NPD651 Clinical (unspecified phase)
0.6667 Remote Similarity NPD6584 Phase 3
0.6667 Remote Similarity NPD16 Approved
0.6667 Remote Similarity NPD856 Approved
0.6667 Remote Similarity NPD9073 Approved
0.6667 Remote Similarity NPD1091 Approved
0.6642 Remote Similarity NPD1511 Approved
0.664 Remote Similarity NPD3225 Approved
0.6639 Remote Similarity NPD3095 Discontinued
0.6639 Remote Similarity NPD17 Approved
0.6639 Remote Similarity NPD4589 Approved
0.6615 Remote Similarity NPD3062 Approved
0.6615 Remote Similarity NPD2238 Phase 2
0.6615 Remote Similarity NPD3061 Approved
0.6615 Remote Similarity NPD1558 Phase 1
0.6615 Remote Similarity NPD3059 Approved
0.6613 Remote Similarity NPD2232 Approved
0.6613 Remote Similarity NPD2230 Approved
0.6613 Remote Similarity NPD2235 Phase 2
0.6613 Remote Similarity NPD2233 Approved
0.6613 Remote Similarity NPD2231 Phase 2
0.6612 Remote Similarity NPD5304 Approved
0.6612 Remote Similarity NPD1759 Phase 1
0.6612 Remote Similarity NPD9545 Approved
0.6612 Remote Similarity NPD5303 Approved
0.6612 Remote Similarity NPD1182 Approved
0.6587 Remote Similarity NPD1203 Approved
0.6587 Remote Similarity NPD4103 Phase 2
0.6587 Remote Similarity NPD4104 Clinical (unspecified phase)
0.6585 Remote Similarity NPD3421 Phase 3
0.6583 Remote Similarity NPD7325 Clinical (unspecified phase)
0.6577 Remote Similarity NPD1616 Discontinued
0.6567 Remote Similarity NPD1550 Clinical (unspecified phase)
0.6567 Remote Similarity NPD1552 Clinical (unspecified phase)
0.656 Remote Similarity NPD1755 Approved
0.6557 Remote Similarity NPD1357 Approved
0.6552 Remote Similarity NPD5451 Approved
0.6547 Remote Similarity NPD1512 Approved
0.6544 Remote Similarity NPD3750 Approved
0.6544 Remote Similarity NPD3892 Phase 2
0.6535 Remote Similarity NPD9621 Approved
0.6535 Remote Similarity NPD9619 Approved
0.6535 Remote Similarity NPD9620 Approved
0.6532 Remote Similarity NPD1535 Discovery
0.6529 Remote Similarity NPD5536 Phase 2
0.6529 Remote Similarity NPD1758 Phase 1
0.6522 Remote Similarity NPD7390 Discontinued
0.6522 Remote Similarity NPD4357 Discontinued
0.6519 Remote Similarity NPD970 Clinical (unspecified phase)
0.6519 Remote Similarity NPD1549 Phase 2
0.6515 Remote Similarity NPD5314 Approved
0.6508 Remote Similarity NPD1283 Approved
0.6504 Remote Similarity NPD1778 Approved
0.6504 Remote Similarity NPD2423 Clinical (unspecified phase)
0.65 Remote Similarity NPD255 Approved

  Bioactivity similarity: Similar Natural Products in NPASS

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