Structure

Physi-Chem Properties

Molecular Weight:  138.03
Volume:  130.977
LogP:  1.214
LogD:  1.331
LogS:  -1.251
# Rotatable Bonds:  0
TPSA:  38.69
# H-Bond Aceptor:  3
# H-Bond Donor:  1
# Rings:  2
# Heavy Atoms:  3

MedChem Properties

QED Drug-Likeness Score:  0.583
Synthetic Accessibility Score:  1.839
Fsp3:  0.143
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Accepted
BMS Rule:  0
Golden Triangle Rule:  Rejected
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.492
MDCK Permeability:  2.5779581847018562e-05
Pgp-inhibitor:  0.001
Pgp-substrate:  0.001
Human Intestinal Absorption (HIA):  0.003
20% Bioavailability (F20%):  0.003
30% Bioavailability (F30%):  0.09

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.137
Plasma Protein Binding (PPB):  79.20179748535156%
Volume Distribution (VD):  2.054
Pgp-substrate:  13.616765975952148%

ADMET: Metabolism

CYP1A2-inhibitor:  0.993
CYP1A2-substrate:  0.358
CYP2C19-inhibitor:  0.757
CYP2C19-substrate:  0.367
CYP2C9-inhibitor:  0.13
CYP2C9-substrate:  0.923
CYP2D6-inhibitor:  0.957
CYP2D6-substrate:  0.909
CYP3A4-inhibitor:  0.699
CYP3A4-substrate:  0.198

ADMET: Excretion

Clearance (CL):  16.789
Half-life (T1/2):  0.849

ADMET: Toxicity

hERG Blockers:  0.028
Human Hepatotoxicity (H-HT):  0.045
Drug-inuced Liver Injury (DILI):  0.092
AMES Toxicity:  0.125
Rat Oral Acute Toxicity:  0.415
Maximum Recommended Daily Dose:  0.035
Skin Sensitization:  0.871
Carcinogencity:  0.937
Eye Corrosion:  0.892
Eye Irritation:  0.984
Respiratory Toxicity:  0.559

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  Natural Product: NPC247871

Natural Product ID:  NPC247871
Common Name*:   Sesamol
IUPAC Name:   1,3-benzodioxol-5-ol
Synonyms:  
Standard InCHIKey:  LUSZGTFNYDARNI-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C7H6O3/c8-5-1-2-6-7(3-5)10-4-9-6/h1-3,8H,4H2
SMILES:  c1cc2c(cc1O)OCO2
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL1517998
PubChem CID:   68289
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000002] Organoheterocyclic compounds
      • [CHEMONTID:0000296] Benzodioxoles

*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
NPO24778 Sesamum orientale Species Pedaliaceae Eukaryota n.a. seed n.a. PMID[11540412]
NPO31494 Acanthopanax senticosus n.a. n.a. n.a. n.a. leaf n.a. PMID[11816040]
NPO9290 Zanthoxylum piperitum Species Rutaceae Eukaryota n.a. leaf n.a. PMID[15388977]
NPO26237 Piper longum Species Piperaceae Eukaryota n.a. n.a. n.a. PMID[16872768]
NPO31494 Acanthopanax senticosus n.a. n.a. n.a. n.a. n.a. n.a. PMID[17125224]
NPO11872 Eleutherococcus senticosus Species Araliaceae Eukaryota n.a. leaf n.a. PMID[17125224]
NPO9290 Zanthoxylum piperitum Species Rutaceae Eukaryota n.a. stem n.a. PMID[17202689]
NPO22079 Paulownia tomentosa Species Paulowniaceae Eukaryota fruits n.a. n.a. PMID[17625893]
NPO22079 Paulownia tomentosa Species Paulowniaceae Eukaryota Fruits n.a. n.a. PMID[18293924]
NPO22079 Paulownia tomentosa Species Paulowniaceae Eukaryota n.a. n.a. n.a. PMID[20192247]
NPO9290 Zanthoxylum piperitum Species Rutaceae Eukaryota n.a. pericarp n.a. PMID[20628994]
NPO26237 Piper longum Species Piperaceae Eukaryota fruits n.a. n.a. PMID[20839888]
NPO22079 Paulownia tomentosa Species Paulowniaceae Eukaryota n.a. fruit n.a. PMID[21319773]
NPO6336 Asarum sieboldii Species Aristolochiaceae Eukaryota roots n.a. n.a. PMID[22381047]
NPO22079 Paulownia tomentosa Species Paulowniaceae Eukaryota fruits n.a. n.a. PMID[22445674]
NPO30633 Acanthopanax sessiliflorus n.a. n.a. n.a. Fruits n.a. n.a. PMID[22691179]
NPO26237 Piper longum Species Piperaceae Eukaryota n.a. n.a. n.a. PMID[23434420]
NPO22079 Paulownia tomentosa Species Paulowniaceae Eukaryota fruits n.a. n.a. PMID[23623680]
NPO29744 Acanthopanax gracilistylus n.a. n.a. n.a. Root Bark n.a. n.a. PMID[25338180]
NPO22079 Paulownia tomentosa Species Paulowniaceae Eukaryota fruits n.a. n.a. PMID[25735399]
NPO11872 Eleutherococcus senticosus Species Araliaceae Eukaryota leaves n.a. n.a. PMID[27400231]
NPO22079 Paulownia tomentosa Species Paulowniaceae Eukaryota Fruits n.a. n.a. PMID[28322565]
NPO22079 Paulownia tomentosa Species Paulowniaceae Eukaryota Fruits n.a. n.a. PMID[28968119]
NPO31494 Acanthopanax senticosus n.a. n.a. n.a. Barks Iksan, Chunbuk, Korea n.a. PMID[3127544]
NPO8500 Acanthopanax gracilistylus Species Araliaceae Eukaryota n.a. n.a. n.a. PMID[32319765]
NPO24778 Sesamum orientale Species Pedaliaceae Eukaryota n.a. n.a. Database[FooDB]
NPO24778 Sesamum orientale Species Pedaliaceae Eukaryota Leaf n.a. n.a. Database[FooDB]
NPO24778 Sesamum orientale Species Pedaliaceae Eukaryota Seed n.a. n.a. Database[FooDB]
NPO24778 Sesamum orientale Species Pedaliaceae Eukaryota n.a. n.a. Database[FooDB]
NPO30633 Acanthopanax sessiliflorus n.a. n.a. n.a. n.a. n.a. n.a. Database[HerDing]
NPO1382 Hyptis tomentosa Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO20362 Ruta montana Species Rutaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO3404 Magnolia mutabilis Species Magnoliaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO26237 Piper longum Species Piperaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO24778 Sesamum orientale Species Pedaliaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO31494 Acanthopanax senticosus n.a. n.a. n.a. n.a. n.a. n.a. Database[HerDing]
NPO542 Artemisia absinthium Species Asteraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO29744 Acanthopanax gracilistylus n.a. n.a. n.a. n.a. n.a. n.a. Database[HerDing]
NPO14512 Oleum sesami n.a. n.a. n.a. n.a. n.a. n.a. Database[HerDing]
NPO22079 Paulownia tomentosa Species Paulowniaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO6336 Asarum sieboldii Species Aristolochiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO9290 Zanthoxylum piperitum Species Rutaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO11387 Semen sesami n.a. n.a. n.a. n.a. n.a. n.a. Database[HerDing]
NPO26237 Piper longum Species Piperaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO11809 Eleutherococcus sessiliflorus Species Araliaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO20362 Ruta montana Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO9290 Zanthoxylum piperitum Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO6336 Asarum sieboldii Species Aristolochiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO1382 Hyptis tomentosa Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO3404 Magnolia mutabilis Species Magnoliaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO14512 Oleum sesami n.a. n.a. n.a. n.a. n.a. n.a. Database[TCMID]
NPO11872 Eleutherococcus senticosus Species Araliaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO24778 Sesamum orientale Species Pedaliaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO8500 Acanthopanax gracilistylus Species Araliaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO22079 Paulownia tomentosa Species Paulowniaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO11387 Semen sesami n.a. n.a. n.a. n.a. n.a. n.a. Database[TCMID]
NPO542 Artemisia absinthium Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO542 Artemisia absinthium Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO22079 Paulownia tomentosa Species Paulowniaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO26237 Piper longum Species Piperaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO24778 Sesamum orientale Species Pedaliaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO9290 Zanthoxylum piperitum Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO3404 Magnolia mutabilis Species Magnoliaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO6336 Asarum sieboldii Species Aristolochiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO30633 Acanthopanax sessiliflorus n.a. n.a. n.a. n.a. n.a. n.a. Database[TCM_Taiwan]
NPO1382 Hyptis tomentosa Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO31494 Acanthopanax senticosus n.a. n.a. n.a. n.a. n.a. n.a. Database[TCM_Taiwan]
NPO29744 Acanthopanax gracilistylus n.a. n.a. n.a. n.a. n.a. n.a. Database[TCM_Taiwan]
NPO20362 Ruta montana Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO6336 Asarum sieboldii Species Aristolochiaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO24778 Sesamum orientale Species Pedaliaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO11872 Eleutherococcus senticosus Species Araliaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO9290 Zanthoxylum piperitum Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO26237 Piper longum Species Piperaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO8500 Acanthopanax gracilistylus Species Araliaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO8500 Acanthopanax gracilistylus Species Araliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11872 Eleutherococcus senticosus Species Araliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22079 Paulownia tomentosa Species Paulowniaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24778 Sesamum orientale Species Pedaliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26237 Piper longum Species Piperaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3404 Magnolia mutabilis Species Magnoliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11809 Eleutherococcus sessiliflorus Species Araliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6336 Asarum sieboldii Species Aristolochiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1382 Hyptis tomentosa Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9290 Zanthoxylum piperitum Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20362 Ruta montana Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO542 Artemisia absinthium Species Asteraceae 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
NPO24778 NPC247871 Oil n.a. 21.54540562 n.a. n.a. mg/100g Database [PHENOL EXPLORER]
NPO24778 NPC247871 Oil n.a. 24.92449951 n.a. n.a. mg/100g Database [PHENOL EXPLORER]

☑ 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
NPT109 Individual Protein Cytochrome P450 3A4 Homo sapiens Potency = 15848.9 nM PMID[449661]
NPT153 Individual Protein Androgen Receptor Homo sapiens Potency n.a. 5011.9 nM PMID[449661]
NPT153 Individual Protein Androgen Receptor Homo sapiens Potency n.a. 35481.3 nM PMID[449661]
NPT71 Cell Line HEK293 Homo sapiens Inhibition = 10.1 % PMID[449662]
NPT12 Individual Protein Human immunodeficiency virus type 1 integrase Human immunodeficiency virus 1 Kd = 5500000.0 nM PMID[449664]
NPT153 Individual Protein Androgen Receptor Homo sapiens Potency n.a. 10782.3 nM PubChem BioAssay data set
NPT153 Individual Protein Androgen Receptor Homo sapiens Potency n.a. 273.2 nM PubChem BioAssay data set
NPT153 Individual Protein Androgen Receptor Homo sapiens Potency n.a. 60.6 nM PubChem BioAssay data set
NPT99 Individual Protein Peroxisome proliferator-activated receptor gamma Homo sapiens Potency n.a. 15848.9 nM PMID[449661]
NPT2632 Organism Syrian golden hamster Mesocricetus auratus Activity = 31.5 % PMID[449663]
NPT2632 Organism Syrian golden hamster Mesocricetus auratus Activity = 47.3 % PMID[449663]
NPT2632 Organism Syrian golden hamster Mesocricetus auratus Activity = 9.5 % PMID[449663]
NPT2632 Organism Syrian golden hamster Mesocricetus auratus Activity = 5.7 % PMID[449663]
NPT35 Others n.a. Activity = 74.94 % PMID[449665]
NPT35 Others n.a. Activity = 72.76 % PMID[449665]
NPT35 Others n.a. Activity = 66.14 % PMID[449665]
NPT35 Others n.a. Activity = 55.12 % PMID[449665]
NPT35 Others n.a. Activity = 30.62 % PMID[449665]
NPT35 Others n.a. Activity = 12.76 % PMID[449665]
NPT35 Others n.a. Activity = 82.63 % PMID[449665]
NPT35 Others n.a. Activity = 81.91 % PMID[449665]
NPT35 Others n.a. Activity = 75.37 % PMID[449665]
NPT35 Others n.a. Activity = 56.36 % PMID[449665]
NPT35 Others n.a. Activity = 29.66 % PMID[449665]
NPT35 Others n.a. Activity = 12.36 % PMID[449665]
NPT35 Others n.a. Activity = 69.62 % PMID[449665]
NPT35 Others n.a. Activity = 70.32 % PMID[449665]
NPT35 Others n.a. Activity = 63.29 % PMID[449665]
NPT35 Others n.a. Activity = 27.76 % PMID[449665]
NPT35 Others n.a. Activity = 52.74 % PMID[449665]
NPT35 Others n.a. Activity = 12.07 % PMID[449665]
NPT35 Others n.a. Activity = 70.81 % PMID[449665]
NPT35 Others n.a. Activity = 71.52 % PMID[449665]
NPT35 Others n.a. Activity = 67.44 % PMID[449665]
NPT35 Others n.a. Activity = 30.22 % PMID[449665]
NPT35 Others n.a. Activity = 56.2 % PMID[449665]
NPT35 Others n.a. Activity = 13.01 % PMID[449665]
NPT2 Others Unspecified Potency n.a. 48559.1 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 3038.9 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 60633.6 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 68032 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 54039.7 nM PubChem BioAssay data set

☑ 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 NPC247871 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
0.8962 High Similarity NPC124712
0.8868 High Similarity NPC232654
0.8598 High Similarity NPC307875
0.8403 Intermediate Similarity NPC221090
0.839 Intermediate Similarity NPC152722
0.8319 Intermediate Similarity NPC192810
0.8269 Intermediate Similarity NPC16649
0.8264 Intermediate Similarity NPC298845
0.822 Intermediate Similarity NPC276195
0.8197 Intermediate Similarity NPC37074
0.8197 Intermediate Similarity NPC469621
0.8115 Intermediate Similarity NPC469622
0.8115 Intermediate Similarity NPC189589
0.8115 Intermediate Similarity NPC171533
0.8099 Intermediate Similarity NPC25817
0.8034 Intermediate Similarity NPC9248
0.8034 Intermediate Similarity NPC33271
0.8017 Intermediate Similarity NPC217854
0.8 Intermediate Similarity NPC60756
0.7981 Intermediate Similarity NPC288923
0.7967 Intermediate Similarity NPC473960
0.7951 Intermediate Similarity NPC191768
0.7951 Intermediate Similarity NPC283170
0.7951 Intermediate Similarity NPC92869
0.7937 Intermediate Similarity NPC287780
0.7934 Intermediate Similarity NPC211231
0.7931 Intermediate Similarity NPC142319
0.7925 Intermediate Similarity NPC114325
0.792 Intermediate Similarity NPC470633
0.792 Intermediate Similarity NPC228769
0.7899 Intermediate Similarity NPC119949
0.7881 Intermediate Similarity NPC76915
0.7881 Intermediate Similarity NPC151617
0.7857 Intermediate Similarity NPC63574
0.7857 Intermediate Similarity NPC208769
0.7851 Intermediate Similarity NPC285289
0.784 Intermediate Similarity NPC247146
0.7812 Intermediate Similarity NPC60982
0.7788 Intermediate Similarity NPC157213
0.7769 Intermediate Similarity NPC197166
0.775 Intermediate Similarity NPC214289
0.7731 Intermediate Similarity NPC259638
0.7727 Intermediate Similarity NPC284464
0.7717 Intermediate Similarity NPC184814
0.7714 Intermediate Similarity NPC302546
0.7698 Intermediate Similarity NPC19694
0.7692 Intermediate Similarity NPC280254
0.7674 Intermediate Similarity NPC58585
0.7674 Intermediate Similarity NPC471391
0.7674 Intermediate Similarity NPC471390
0.7667 Intermediate Similarity NPC228907
0.7661 Intermediate Similarity NPC183446
0.7652 Intermediate Similarity NPC6369
0.7652 Intermediate Similarity NPC30951
0.7652 Intermediate Similarity NPC9068
0.7647 Intermediate Similarity NPC193067
0.7636 Intermediate Similarity NPC314803
0.7623 Intermediate Similarity NPC205850
0.7619 Intermediate Similarity NPC47422
0.7603 Intermediate Similarity NPC20674
0.7576 Intermediate Similarity NPC195196
0.7556 Intermediate Similarity NPC474808
0.7544 Intermediate Similarity NPC473653
0.7541 Intermediate Similarity NPC229401
0.754 Intermediate Similarity NPC112596
0.7538 Intermediate Similarity NPC112237
0.7538 Intermediate Similarity NPC132895
0.7538 Intermediate Similarity NPC196937
0.7524 Intermediate Similarity NPC206876
0.7519 Intermediate Similarity NPC292487
0.75 Intermediate Similarity NPC474864
0.75 Intermediate Similarity NPC172818
0.75 Intermediate Similarity NPC270326
0.75 Intermediate Similarity NPC135414
0.75 Intermediate Similarity NPC104167
0.75 Intermediate Similarity NPC126216
0.75 Intermediate Similarity NPC105147
0.75 Intermediate Similarity NPC228875
0.75 Intermediate Similarity NPC246967
0.75 Intermediate Similarity NPC25695
0.748 Intermediate Similarity NPC166759
0.7462 Intermediate Similarity NPC470270
0.7451 Intermediate Similarity NPC270094
0.7445 Intermediate Similarity NPC474749
0.7445 Intermediate Similarity NPC178014
0.7445 Intermediate Similarity NPC42716
0.7445 Intermediate Similarity NPC11422
0.7444 Intermediate Similarity NPC474039
0.7438 Intermediate Similarity NPC304208
0.7438 Intermediate Similarity NPC52464
0.7422 Intermediate Similarity NPC63179
0.7422 Intermediate Similarity NPC266691
0.7419 Intermediate Similarity NPC57751
0.7419 Intermediate Similarity NPC75713
0.7405 Intermediate Similarity NPC49074
0.7402 Intermediate Similarity NPC245060
0.7398 Intermediate Similarity NPC247364
0.7398 Intermediate Similarity NPC61516
0.7398 Intermediate Similarity NPC474565
0.7398 Intermediate Similarity NPC232084
0.7398 Intermediate Similarity NPC10932
0.7391 Intermediate Similarity NPC164576
0.7391 Intermediate Similarity NPC33832
0.7377 Intermediate Similarity NPC474612
0.7373 Intermediate Similarity NPC203924
0.7364 Intermediate Similarity NPC190144
0.7364 Intermediate Similarity NPC58164
0.7364 Intermediate Similarity NPC10225
0.736 Intermediate Similarity NPC71579
0.736 Intermediate Similarity NPC473411
0.736 Intermediate Similarity NPC262253
0.7353 Intermediate Similarity NPC4154
0.735 Intermediate Similarity NPC165386
0.735 Intermediate Similarity NPC127326
0.7348 Intermediate Similarity NPC7163
0.7348 Intermediate Similarity NPC107478
0.7344 Intermediate Similarity NPC216836
0.7333 Intermediate Similarity NPC177868
0.7328 Intermediate Similarity NPC299144
0.7328 Intermediate Similarity NPC162093
0.7328 Intermediate Similarity NPC252833
0.7323 Intermediate Similarity NPC58279
0.7323 Intermediate Similarity NPC300326
0.7323 Intermediate Similarity NPC12308
0.7319 Intermediate Similarity NPC307466
0.7317 Intermediate Similarity NPC226629
0.7317 Intermediate Similarity NPC308217
0.7313 Intermediate Similarity NPC65530
0.7313 Intermediate Similarity NPC59324
0.7313 Intermediate Similarity NPC185908
0.7308 Intermediate Similarity NPC220935
0.7308 Intermediate Similarity NPC224157
0.7308 Intermediate Similarity NPC299221
0.7308 Intermediate Similarity NPC51840
0.7308 Intermediate Similarity NPC192687
0.7308 Intermediate Similarity NPC229231
0.7308 Intermediate Similarity NPC311680
0.7308 Intermediate Similarity NPC234488
0.7302 Intermediate Similarity NPC220598
0.7302 Intermediate Similarity NPC165375
0.7302 Intermediate Similarity NPC282496
0.7302 Intermediate Similarity NPC238810
0.7302 Intermediate Similarity NPC233526
0.7302 Intermediate Similarity NPC95168
0.7299 Intermediate Similarity NPC252169
0.7299 Intermediate Similarity NPC298317
0.7299 Intermediate Similarity NPC255566
0.7293 Intermediate Similarity NPC134968
0.7293 Intermediate Similarity NPC150534
0.7288 Intermediate Similarity NPC31279
0.7288 Intermediate Similarity NPC94045
0.7286 Intermediate Similarity NPC301961
0.7286 Intermediate Similarity NPC166584
0.728 Intermediate Similarity NPC49341
0.728 Intermediate Similarity NPC310373
0.7273 Intermediate Similarity NPC6836
0.7266 Intermediate Similarity NPC162193
0.7266 Intermediate Similarity NPC226540
0.7266 Intermediate Similarity NPC110677
0.7259 Intermediate Similarity NPC212770
0.7259 Intermediate Similarity NPC98777
0.7252 Intermediate Similarity NPC166168
0.7252 Intermediate Similarity NPC82503
0.7252 Intermediate Similarity NPC45715
0.7252 Intermediate Similarity NPC12275
0.7252 Intermediate Similarity NPC474356
0.725 Intermediate Similarity NPC204120
0.7246 Intermediate Similarity NPC297342
0.7244 Intermediate Similarity NPC206487
0.7244 Intermediate Similarity NPC5796
0.7241 Intermediate Similarity NPC41594
0.7239 Intermediate Similarity NPC242028
0.7239 Intermediate Similarity NPC203230
0.7239 Intermediate Similarity NPC164857
0.7238 Intermediate Similarity NPC23837
0.7236 Intermediate Similarity NPC63083
0.7231 Intermediate Similarity NPC218003
0.7231 Intermediate Similarity NPC45824
0.7231 Intermediate Similarity NPC307110
0.7231 Intermediate Similarity NPC158477
0.7226 Intermediate Similarity NPC184684
0.7226 Intermediate Similarity NPC133934
0.7226 Intermediate Similarity NPC184641
0.7226 Intermediate Similarity NPC41782
0.7222 Intermediate Similarity NPC41562
0.7218 Intermediate Similarity NPC470881
0.7218 Intermediate Similarity NPC13745
0.7218 Intermediate Similarity NPC48863
0.7218 Intermediate Similarity NPC251981
0.7214 Intermediate Similarity NPC116019
0.7209 Intermediate Similarity NPC50368
0.72 Intermediate Similarity NPC199023
0.7197 Intermediate Similarity NPC161203
0.7197 Intermediate Similarity NPC6451
0.7197 Intermediate Similarity NPC471505
0.7194 Intermediate Similarity NPC180953
0.7188 Intermediate Similarity NPC234400
0.7188 Intermediate Similarity NPC17943
0.7188 Intermediate Similarity NPC251855
0.7188 Intermediate Similarity NPC472093

  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 NPC247871 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
0.7925 Intermediate Similarity NPD9296 Approved
0.7788 Intermediate Similarity NPD9295 Approved
0.7692 Intermediate Similarity NPD9094 Approved
0.7451 Intermediate Similarity NPD9089 Approved
0.7353 Intermediate Similarity NPD9093 Approved
0.7345 Intermediate Similarity NPD291 Approved
0.7317 Intermediate Similarity NPD1357 Approved
0.7203 Intermediate Similarity NPD556 Approved
0.7185 Intermediate Similarity NPD3454 Phase 3
0.7143 Intermediate Similarity NPD1091 Approved
0.7099 Intermediate Similarity NPD3027 Phase 3
0.7059 Intermediate Similarity NPD9088 Approved
0.7016 Intermediate Similarity NPD1408 Clinical (unspecified phase)
0.7008 Intermediate Similarity NPD3705 Approved
0.7 Intermediate Similarity NPD9365 Approved
0.6993 Remote Similarity NPD1653 Approved
0.696 Remote Similarity NPD7534 Approved
0.696 Remote Similarity NPD7533 Approved
0.6942 Remote Similarity NPD228 Approved
0.6894 Remote Similarity NPD1529 Clinical (unspecified phase)
0.6825 Remote Similarity NPD1548 Phase 1
0.6818 Remote Similarity NPD1530 Clinical (unspecified phase)
0.6815 Remote Similarity NPD1612 Clinical (unspecified phase)
0.6815 Remote Similarity NPD1613 Approved
0.6807 Remote Similarity NPD968 Approved
0.6774 Remote Similarity NPD9299 Approved
0.6769 Remote Similarity NPD2983 Phase 2
0.6769 Remote Similarity NPD2982 Phase 2
0.6692 Remote Similarity NPD2981 Phase 2
0.6667 Remote Similarity NPD9087 Approved
0.6615 Remote Similarity NPD1610 Phase 2
0.6615 Remote Similarity NPD422 Phase 1
0.6577 Remote Similarity NPD37 Approved
0.6567 Remote Similarity NPD3018 Phase 2
0.6475 Remote Similarity NPD9552 Approved
0.6475 Remote Similarity NPD290 Approved
0.6471 Remote Similarity NPD6234 Discontinued
0.6467 Remote Similarity NPD3383 Approved
0.6467 Remote Similarity NPD3382 Approved
0.6467 Remote Similarity NPD3384 Approved
0.6447 Remote Similarity NPD4966 Approved
0.6447 Remote Similarity NPD4965 Approved
0.6447 Remote Similarity NPD4967 Phase 2
0.6397 Remote Similarity NPD3537 Clinical (unspecified phase)
0.6387 Remote Similarity NPD1242 Phase 1
0.637 Remote Similarity NPD6143 Clinical (unspecified phase)
0.6364 Remote Similarity NPD9501 Approved
0.6351 Remote Similarity NPD6980 Clinical (unspecified phase)
0.6333 Remote Similarity NPD940 Approved
0.6333 Remote Similarity NPD846 Approved
0.6328 Remote Similarity NPD191 Approved
0.6289 Remote Similarity NPD3818 Discontinued
0.6288 Remote Similarity NPD915 Approved
0.6277 Remote Similarity NPD4908 Phase 1
0.6269 Remote Similarity NPD4749 Approved
0.6269 Remote Similarity NPD4379 Clinical (unspecified phase)
0.6259 Remote Similarity NPD4357 Discontinued
0.6233 Remote Similarity NPD2219 Phase 1
0.6209 Remote Similarity NPD2801 Approved
0.6204 Remote Similarity NPD2861 Phase 2
0.6202 Remote Similarity NPD6671 Approved
0.6188 Remote Similarity NPD7228 Approved
0.6187 Remote Similarity NPD4907 Clinical (unspecified phase)
0.6181 Remote Similarity NPD1375 Discontinued
0.6178 Remote Similarity NPD7199 Phase 2
0.6172 Remote Similarity NPD5283 Phase 1
0.617 Remote Similarity NPD230 Phase 1
0.6164 Remote Similarity NPD1878 Clinical (unspecified phase)
0.616 Remote Similarity NPD2684 Approved
0.6143 Remote Similarity NPD554 Clinical (unspecified phase)
0.6136 Remote Similarity NPD1797 Approved
0.6136 Remote Similarity NPD1798 Approved
0.6131 Remote Similarity NPD6917 Clinical (unspecified phase)
0.6115 Remote Similarity NPD4625 Phase 3
0.6104 Remote Similarity NPD2978 Approved
0.6104 Remote Similarity NPD2977 Approved
0.6103 Remote Similarity NPD6696 Suspended
0.6101 Remote Similarity NPD7184 Clinical (unspecified phase)
0.6099 Remote Similarity NPD1240 Approved
0.6099 Remote Similarity NPD1558 Phase 1
0.6098 Remote Similarity NPD4338 Clinical (unspecified phase)
0.6087 Remote Similarity NPD9494 Approved
0.608 Remote Similarity NPD1358 Approved
0.6071 Remote Similarity NPD6859 Clinical (unspecified phase)
0.6071 Remote Similarity NPD6410 Clinical (unspecified phase)
0.6069 Remote Similarity NPD7266 Discontinued
0.6069 Remote Similarity NPD3540 Phase 1
0.6056 Remote Similarity NPD447 Suspended
0.6049 Remote Similarity NPD7054 Approved
0.6045 Remote Similarity NPD155 Clinical (unspecified phase)
0.604 Remote Similarity NPD1511 Approved
0.6039 Remote Similarity NPD1934 Approved
0.6026 Remote Similarity NPD3882 Suspended
0.6018 Remote Similarity NPD9073 Approved
0.6018 Remote Similarity NPD111 Approved
0.6016 Remote Similarity NPD969 Suspended
0.6014 Remote Similarity NPD1772 Clinical (unspecified phase)
0.6014 Remote Similarity NPD2492 Phase 1
0.6014 Remote Similarity NPD1607 Approved
0.6013 Remote Similarity NPD4678 Approved
0.6013 Remote Similarity NPD4675 Approved
0.6012 Remote Similarity NPD7472 Approved
0.6012 Remote Similarity NPD7074 Phase 3
0.6 Remote Similarity NPD1535 Discovery
0.6 Remote Similarity NPD1551 Phase 2
0.6 Remote Similarity NPD3539 Phase 1
0.5987 Remote Similarity NPD5604 Discontinued
0.5987 Remote Similarity NPD4381 Clinical (unspecified phase)
0.5987 Remote Similarity NPD7975 Clinical (unspecified phase)
0.5986 Remote Similarity NPD1652 Phase 2
0.5985 Remote Similarity NPD1102 Approved
0.5985 Remote Similarity NPD1103 Approved
0.5985 Remote Similarity NPD9092 Discovery
0.5985 Remote Similarity NPD5536 Phase 2
0.5973 Remote Similarity NPD5058 Phase 3
0.5972 Remote Similarity NPD6111 Discontinued
0.5969 Remote Similarity NPD7843 Approved
0.5969 Remote Similarity NPD1138 Approved
0.596 Remote Similarity NPD1940 Clinical (unspecified phase)
0.596 Remote Similarity NPD1512 Approved
0.5959 Remote Similarity NPD521 Clinical (unspecified phase)
0.5957 Remote Similarity NPD3145 Approved
0.5957 Remote Similarity NPD3144 Approved
0.5956 Remote Similarity NPD1481 Phase 2
0.5956 Remote Similarity NPD9269 Phase 2
0.595 Remote Similarity NPD9097 Approved
0.595 Remote Similarity NPD9096 Approved
0.595 Remote Similarity NPD9095 Approved
0.595 Remote Similarity NPD68 Approved
0.5944 Remote Similarity NPD1933 Approved
0.5942 Remote Similarity NPD2082 Clinical (unspecified phase)
0.5942 Remote Similarity NPD3827 Clinical (unspecified phase)
0.5938 Remote Similarity NPD2673 Approved
0.5938 Remote Similarity NPD2671 Approved
0.5938 Remote Similarity NPD9280 Clinical (unspecified phase)
0.5933 Remote Similarity NPD5297 Approved
0.5931 Remote Similarity NPD1510 Phase 2
0.5926 Remote Similarity NPD3496 Discontinued
0.5915 Remote Similarity NPD2674 Phase 3
0.5906 Remote Similarity NPD5307 Clinical (unspecified phase)
0.5904 Remote Similarity NPD7808 Phase 3
0.5896 Remote Similarity NPD9268 Approved
0.5891 Remote Similarity NPD1137 Approved
0.5891 Remote Similarity NPD1139 Approved
0.5882 Remote Similarity NPD776 Approved
0.5879 Remote Similarity NPD6797 Phase 2
0.5878 Remote Similarity NPD4236 Phase 3
0.5878 Remote Similarity NPD4237 Approved
0.5878 Remote Similarity NPD6674 Discontinued
0.5874 Remote Similarity NPD3619 Clinical (unspecified phase)
0.5874 Remote Similarity NPD3620 Phase 2
0.5873 Remote Similarity NPD3134 Approved
0.587 Remote Similarity NPD3225 Approved
0.5859 Remote Similarity NPD4750 Phase 3
0.5854 Remote Similarity NPD289 Clinical (unspecified phase)
0.5852 Remote Similarity NPD1778 Approved
0.585 Remote Similarity NPD1550 Clinical (unspecified phase)
0.585 Remote Similarity NPD1552 Clinical (unspecified phase)
0.5846 Remote Similarity NPD821 Approved
0.5846 Remote Similarity NPD769 Approved
0.5843 Remote Similarity NPD7251 Discontinued
0.5843 Remote Similarity NPD7240 Approved
0.5839 Remote Similarity NPD6232 Discontinued
0.5833 Remote Similarity NPD709 Approved
0.5833 Remote Similarity NPD7157 Approved
0.5833 Remote Similarity NPD7090 Clinical (unspecified phase)
0.5827 Remote Similarity NPD1049 Clinical (unspecified phase)
0.5823 Remote Similarity NPD4868 Clinical (unspecified phase)
0.5821 Remote Similarity NPD9545 Approved
0.582 Remote Similarity NPD9273 Approved
0.5816 Remote Similarity NPD600 Approved
0.5816 Remote Similarity NPD596 Approved
0.5811 Remote Similarity NPD970 Clinical (unspecified phase)
0.5811 Remote Similarity NPD1549 Phase 2
0.5804 Remote Similarity NPD6233 Phase 2
0.5804 Remote Similarity NPD1726 Clinical (unspecified phase)
0.5796 Remote Similarity NPD1465 Phase 2
0.5796 Remote Similarity NPD2393 Clinical (unspecified phase)
0.5794 Remote Similarity NPD9697 Approved
0.5789 Remote Similarity NPD9493 Approved
0.5786 Remote Similarity NPD1469 Clinical (unspecified phase)
0.5786 Remote Similarity NPD5647 Approved
0.5772 Remote Similarity NPD3060 Approved
0.5772 Remote Similarity NPD5177 Phase 3
0.5762 Remote Similarity NPD7124 Phase 2
0.5759 Remote Similarity NPD6374 Clinical (unspecified phase)
0.5759 Remote Similarity NPD3817 Phase 2
0.5758 Remote Similarity NPD5844 Phase 1
0.5753 Remote Similarity NPD4978 Clinical (unspecified phase)
0.5749 Remote Similarity NPD6559 Discontinued
0.5745 Remote Similarity NPD2250 Discontinued
0.5742 Remote Similarity NPD4005 Discontinued
0.5742 Remote Similarity NPD6055 Clinical (unspecified phase)
0.5735 Remote Similarity NPD5125 Phase 3
0.5735 Remote Similarity NPD5126 Approved
0.5734 Remote Similarity NPD1048 Approved
0.5733 Remote Similarity NPD3750 Approved
0.5732 Remote Similarity NPD7473 Discontinued
0.5725 Remote Similarity NPD1608 Approved
0.5725 Remote Similarity NPD9717 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