Structure

Physi-Chem Properties

Molecular Weight:  161.08
Volume:  173.645
LogP:  1.661
LogD:  1.438
LogS:  -1.749
# Rotatable Bonds:  2
TPSA:  36.02
# H-Bond Aceptor:  2
# H-Bond Donor:  2
# Rings:  2
# Heavy Atoms:  2

MedChem Properties

QED Drug-Likeness Score:  0.691
Synthetic Accessibility Score:  1.789
Fsp3:  0.2
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:  -4.381
MDCK Permeability:  1.477363912272267e-05
Pgp-inhibitor:  0.004
Pgp-substrate:  0.026
Human Intestinal Absorption (HIA):  0.013
20% Bioavailability (F20%):  0.716
30% Bioavailability (F30%):  0.987

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.834
Plasma Protein Binding (PPB):  57.27055740356445%
Volume Distribution (VD):  1.96
Pgp-substrate:  32.14746856689453%

ADMET: Metabolism

CYP1A2-inhibitor:  0.97
CYP1A2-substrate:  0.815
CYP2C19-inhibitor:  0.64
CYP2C19-substrate:  0.243
CYP2C9-inhibitor:  0.065
CYP2C9-substrate:  0.921
CYP2D6-inhibitor:  0.412
CYP2D6-substrate:  0.842
CYP3A4-inhibitor:  0.142
CYP3A4-substrate:  0.223

ADMET: Excretion

Clearance (CL):  9.564
Half-life (T1/2):  0.878

ADMET: Toxicity

hERG Blockers:  0.029
Human Hepatotoxicity (H-HT):  0.36
Drug-inuced Liver Injury (DILI):  0.193
AMES Toxicity:  0.04
Rat Oral Acute Toxicity:  0.432
Maximum Recommended Daily Dose:  0.249
Skin Sensitization:  0.743
Carcinogencity:  0.151
Eye Corrosion:  0.331
Eye Irritation:  0.989
Respiratory Toxicity:  0.405

Download Data

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  Natural Product: NPC230869

Natural Product ID:  NPC230869
Common Name*:   Tryptophol
IUPAC Name:   2-(1H-indol-3-yl)ethanol
Synonyms:   Tryptophol
Standard InCHIKey:  MBBOMCVGYCRMEA-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C10H11NO/c12-6-5-8-7-11-10-4-2-1-3-9(8)10/h1-4,7,11-12H,5-6H2
SMILES:  OCCc1c[nH]c2c1cccc2
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL226545
PubChem CID:   10685
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000002] Organoheterocyclic compounds
      • [CHEMONTID:0000211] Indoles and derivatives
        • [CHEMONTID:0002497] Indoles
          • [CHEMONTID:0004196] 3-alkylindoles

*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
NPO21658 Saccharomyces cerevisiae Species Saccharomycetaceae Eukaryota n.a. n.a. n.a. DOI[10.1016/0003-9861(62)90112-1]
NPO21658 Saccharomyces cerevisiae Species Saccharomycetaceae Eukaryota n.a. n.a. n.a. PMID[11035032]
NPO32970 epichloë festucae Species n.a. n.a. n.a. n.a. n.a. PMID[11052720]
NPO21658 Saccharomyces cerevisiae Species Saccharomycetaceae Eukaryota n.a. n.a. n.a. PMID[12902239]
NPO21658 Saccharomyces cerevisiae Species Saccharomycetaceae Eukaryota n.a. n.a. n.a. PMID[13835567]
NPO21658 Saccharomyces cerevisiae Species Saccharomycetaceae Eukaryota n.a. n.a. n.a. PMID[14389294]
NPO21658 Saccharomyces cerevisiae Species Saccharomycetaceae Eukaryota n.a. n.a. n.a. PMID[1449509]
NPO21658 Saccharomyces cerevisiae Species Saccharomycetaceae Eukaryota n.a. n.a. n.a. PMID[14607989]
NPO14403 Taiwanofungus camphoratus Species Coriolaceae Eukaryota n.a. fruit body n.a. PMID[15095145]
NPO21658 Saccharomyces cerevisiae Species Saccharomycetaceae Eukaryota n.a. n.a. n.a. PMID[15375647]
NPO21658 Saccharomyces cerevisiae Species Saccharomycetaceae Eukaryota n.a. n.a. n.a. PMID[15744050]
NPO21658 Saccharomyces cerevisiae Species Saccharomycetaceae Eukaryota n.a. n.a. n.a. PMID[16850348]
NPO6984 Brickellia veronicaefolia Species Asteraceae Eukaryota essential oil n.a. n.a. PMID[16933870]
NPO21658 Saccharomyces cerevisiae Species Saccharomycetaceae Eukaryota n.a. n.a. n.a. PMID[17439666]
NPO14403 Taiwanofungus camphoratus Species Coriolaceae Eukaryota n.a. n.a. n.a. PMID[17559265]
NPO4396 Chlorobaculum tepidum Species Chlorobiaceae Bacteria n.a. n.a. n.a. PMID[17586634]
NPO14403 Taiwanofungus camphoratus Species Coriolaceae Eukaryota n.a. mycelium n.a. PMID[17932820]
NPO8737 Saussurea muliensis Species Asteraceae Eukaryota flowers and roots Muli Autonomous County of Sichuan, China 2005-AUG PMID[18419156]
NPO2605 Pichia membranifaciens Species Pichiaceae Eukaryota n.a. n.a. n.a. PMID[19943625]
NPO14403 Taiwanofungus camphoratus Species Coriolaceae Eukaryota fruiting body n.a. n.a. PMID[21028898]
NPO14403 Taiwanofungus camphoratus Species Coriolaceae Eukaryota n.a. fruit body n.a. PMID[21028898]
NPO14403 Taiwanofungus camphoratus Species Coriolaceae Eukaryota fruiting body n.a. n.a. PMID[21115251]
NPO25069 Streptomyces verticillus Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[21210656]
NPO21658 Saccharomyces cerevisiae Species Saccharomycetaceae Eukaryota n.a. n.a. n.a. PMID[22031445]
NPO14403 Taiwanofungus camphoratus Species Coriolaceae Eukaryota n.a. n.a. n.a. PMID[23517145]
NPO21658 Saccharomyces cerevisiae Species Saccharomycetaceae Eukaryota n.a. n.a. n.a. PMID[2405251]
NPO21658 Saccharomyces cerevisiae Species Saccharomycetaceae Eukaryota n.a. n.a. n.a. PMID[24305546]
NPO21658 Saccharomyces cerevisiae Species Saccharomycetaceae Eukaryota n.a. n.a. n.a. PMID[24678285]
NPO21658 Saccharomyces cerevisiae Species Saccharomycetaceae Eukaryota n.a. n.a. n.a. PMID[24733517]
NPO21658 Saccharomyces cerevisiae Species Saccharomycetaceae Eukaryota n.a. n.a. n.a. PMID[24831709]
NPO21658 Saccharomyces cerevisiae Species Saccharomycetaceae Eukaryota n.a. n.a. n.a. PMID[24981409]
NPO4396 Chlorobaculum tepidum Species Chlorobiaceae Bacteria n.a. n.a. n.a. PMID[26088139]
NPO21658 Saccharomyces cerevisiae Species Saccharomycetaceae Eukaryota n.a. n.a. n.a. PMID[2687322]
NPO14403 Taiwanofungus camphoratus Species Coriolaceae Eukaryota n.a. n.a. n.a. PMID[31891260]
NPO21658 Saccharomyces cerevisiae Species Saccharomycetaceae Eukaryota n.a. n.a. n.a. PMID[3289762]
NPO21658 Saccharomyces cerevisiae Species Saccharomycetaceae Eukaryota n.a. n.a. n.a. PMID[4266242]
NPO21658 Saccharomyces cerevisiae Species Saccharomycetaceae Eukaryota n.a. n.a. n.a. PMID[4616942]
NPO21658 Saccharomyces cerevisiae Species Saccharomycetaceae Eukaryota n.a. n.a. n.a. PMID[5764336]
NPO21658 Saccharomyces cerevisiae Species Saccharomycetaceae Eukaryota n.a. n.a. n.a. PMID[6306574]
NPO21658 Saccharomyces cerevisiae Species Saccharomycetaceae Eukaryota n.a. n.a. n.a. PMID[767332]
NPO21658 Saccharomyces cerevisiae Species Saccharomycetaceae Eukaryota n.a. n.a. n.a. PMID[7929110]
NPO21658 Saccharomyces cerevisiae Species Saccharomycetaceae Eukaryota n.a. n.a. n.a. PMID[8017107]
NPO14403 Taiwanofungus camphoratus Species Coriolaceae Eukaryota n.a. fruit body n.a. PMID[8594142]
NPO21658 Saccharomyces cerevisiae Species Saccharomycetaceae Eukaryota n.a. n.a. n.a. PMID[8798704]
NPO21658 Saccharomyces cerevisiae Species Saccharomycetaceae Eukaryota n.a. n.a. n.a. PMID[8852895]
NPO21658 Saccharomyces cerevisiae Species Saccharomycetaceae Eukaryota n.a. n.a. n.a. PMID[8971708]
NPO2676 Anabaena cylindrica Species 0stocaceae Bacteria n.a. n.a. n.a. PMID[9644086]
NPO21658 Saccharomyces cerevisiae Species Saccharomycetaceae Eukaryota n.a. n.a. n.a. PMID[9748245]
NPO695 Picea sitchensis Species Pinaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO3770 Drosera rotundifolia Species Droseraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO7611 Sclerotium poriae cocos Species Typhulaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO9626 Aconitum finetianum Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO9247 Bupleurum smithii Species Apiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO21658 Saccharomyces cerevisiae Species Saccharomycetaceae Eukaryota n.a. n.a. n.a. Database[MetaboLights]
NPO3092 Pycnarrhena ozantha Species Menispermaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO9247 Bupleurum smithii Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO695 Picea sitchensis Species Pinaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO11920 Geraea canescens Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO14403 Taiwanofungus camphoratus Species Coriolaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO3770 Drosera rotundifolia Species Droseraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO12143 Corydalis solida Species Papaveraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO9626 Aconitum finetianum Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO7611 Sclerotium poriae cocos Species Typhulaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO9626 Aconitum finetianum Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO9247 Bupleurum smithii Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO8183 Asplenium viviparum Species Aspleniaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2676 Anabaena cylindrica Species 0stocaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO695 Picea sitchensis Species Pinaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2531 Daniellia oliveri Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO254 Coreopsis capillacea Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1845 Physocarpus opulifolius Species Rosaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6984 Brickellia veronicaefolia Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2605 Pichia membranifaciens Species Pichiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3712 Pedicularis olgae Species Orobanchaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6636 Ophiorrhiza filistipula Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5089 Abies forrestii Species Pinaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24743 Swartschewskia papyracea Species Lubomirskiidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25069 Streptomyces verticillus Species Streptomycetaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO8737 Saussurea muliensis Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3092 Pycnarrhena ozantha Species Menispermaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1378 Peltigera dolichorrhiza Species Peltigeraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9247 Bupleurum smithii Species Apiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10207.1 Olea europaea subsp. cuspidata Subspecies Oleaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12143 Corydalis solida Species Papaveraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10777 Persea lingue Species Lauraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11920 Geraea canescens Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3770 Drosera rotundifolia Species Droseraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4396 Chlorobaculum tepidum Species Chlorobiaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO5944 Guatteria dielsiana Species Annonaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6814 Pegaeophyton scapiflorum Species Brassicaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16977 Centrosema pubescens Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21658 Saccharomyces cerevisiae Species Saccharomycetaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14403 Taiwanofungus camphoratus Species Coriolaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24119 Pilocarpus trachylophus Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4093 Astragalus stipulosus Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO693 Chamaebatia foliolosa Species Rosaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9626 Aconitum finetianum Species Ranunculaceae 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
NPT101 Individual Protein Glucagon-like peptide 1 receptor Homo sapiens Potency n.a. 31622.8 nM PMID[540278]
NPT157 Individual Protein Breast cancer type 1 susceptibility protein Homo sapiens Potency n.a. 316.2 nM PMID[540278]
NPT380 Cell Line U-251 Homo sapiens EC50 = 1220000.0 nM PMID[540281]
NPT27 Others Unspecified LogP app = -4.72 n.a. PMID[540276]
NPT35 Others n.a. LogP = 1.54 n.a. PMID[540276]
NPT1 Others Radical scavenging activity Activity = 52.0 % PMID[540277]
NPT6 Organism Plasmodium falciparum Plasmodium falciparum Potency n.a. 3696.4 nM PMID[540278]
NPT4113 Organism Leptosphaeria maculans Leptosphaeria maculans GI = 16.0 % PMID[540279]
NPT4113 Organism Leptosphaeria maculans Leptosphaeria maculans GI = 29.0 % PMID[540279]
NPT2820 Organism Cryphonectria parasitica Cryphonectria parasitica IZ = 7.0 mm PMID[540280]
NPT2820 Organism Cryphonectria parasitica Cryphonectria parasitica IZ = 9.0 mm PMID[540280]
NPT2820 Organism Cryphonectria parasitica Cryphonectria parasitica IZ = 11.0 mm PMID[540280]
NPT2820 Organism Cryphonectria parasitica Cryphonectria parasitica IZ = 14.0 mm PMID[540280]
NPT2 Others Unspecified Potency n.a. 4466.8 nM PMID[540278]
NPT2 Others Unspecified Potency n.a. 1584.9 nM PMID[540278]
NPT2 Others Unspecified EC50 = 1950000.0 nM PMID[540281]
NPT2 Others Unspecified EC50 = 580000.0 nM PMID[540281]
NPT2 Others Unspecified EC50 = 1740000.0 nM PMID[540281]
NPT2 Others Unspecified EC50 = 4570000.0 nM PMID[540281]

☑ 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 NPC230869 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
0.9408 High Similarity NPC102423
0.9333 High Similarity NPC469785
0.9272 High Similarity NPC469762
0.9161 High Similarity NPC54988
0.915 High Similarity NPC131718
0.9073 High Similarity NPC469763
0.9073 High Similarity NPC73952
0.9073 High Similarity NPC469786
0.9073 High Similarity NPC469765
0.9073 High Similarity NPC469760
0.9073 High Similarity NPC25008
0.9073 High Similarity NPC259644
0.9068 High Similarity NPC71037
0.9051 High Similarity NPC313791
0.9032 High Similarity NPC311276
0.9026 High Similarity NPC279918
0.9013 High Similarity NPC80597
0.9013 High Similarity NPC211572
0.9013 High Similarity NPC75540
0.9013 High Similarity NPC212376
0.9013 High Similarity NPC70922
0.8968 High Similarity NPC282231
0.8926 High Similarity NPC314372
0.8919 High Similarity NPC190296
0.891 High Similarity NPC40779
0.8896 High Similarity NPC469358
0.8882 High Similarity NPC111275
0.8861 High Similarity NPC201700
0.8848 High Similarity NPC315555
0.88 High Similarity NPC159856
0.8797 High Similarity NPC160105
0.8797 High Similarity NPC49954
0.8797 High Similarity NPC474561
0.8788 High Similarity NPC163421
0.8788 High Similarity NPC188387
0.8742 High Similarity NPC63751
0.8742 High Similarity NPC78020
0.869 High Similarity NPC154339
0.865 High Similarity NPC151939
0.8639 High Similarity NPC29886
0.8639 High Similarity NPC96102
0.8639 High Similarity NPC261195
0.8625 High Similarity NPC317430
0.8606 High Similarity NPC233936
0.8581 High Similarity NPC105127
0.8581 High Similarity NPC84911
0.858 High Similarity NPC314603
0.858 High Similarity NPC95783
0.8571 High Similarity NPC105818
0.8571 High Similarity NPC24678
0.8563 High Similarity NPC15102
0.8562 High Similarity NPC471957
0.8554 High Similarity NPC220765
0.8554 High Similarity NPC163055
0.8553 High Similarity NPC194640
0.8538 High Similarity NPC267343
0.8528 High Similarity NPC110500
0.8528 High Similarity NPC149155
0.8528 High Similarity NPC203468
0.8503 High Similarity NPC204717
0.8493 Intermediate Similarity NPC82295
0.8476 Intermediate Similarity NPC267885
0.8467 Intermediate Similarity NPC73767
0.8467 Intermediate Similarity NPC110126
0.8462 Intermediate Similarity NPC46580
0.8452 Intermediate Similarity NPC314002
0.8443 Intermediate Similarity NPC48938
0.8439 Intermediate Similarity NPC251090
0.8434 Intermediate Similarity NPC300688
0.8424 Intermediate Similarity NPC248454
0.8424 Intermediate Similarity NPC184964
0.8424 Intermediate Similarity NPC59269
0.8411 Intermediate Similarity NPC469767
0.8411 Intermediate Similarity NPC469784
0.8411 Intermediate Similarity NPC469783
0.8411 Intermediate Similarity NPC469761
0.8411 Intermediate Similarity NPC469780
0.8411 Intermediate Similarity NPC469768
0.8411 Intermediate Similarity NPC469779
0.8411 Intermediate Similarity NPC279081
0.8402 Intermediate Similarity NPC171171
0.8397 Intermediate Similarity NPC216713
0.8373 Intermediate Similarity NPC126709
0.8373 Intermediate Similarity NPC248041
0.8373 Intermediate Similarity NPC55772
0.8373 Intermediate Similarity NPC283219
0.8355 Intermediate Similarity NPC469766
0.8354 Intermediate Similarity NPC141353
0.8353 Intermediate Similarity NPC317030
0.8313 Intermediate Similarity NPC96890
0.8303 Intermediate Similarity NPC37423
0.8303 Intermediate Similarity NPC275305
0.8294 Intermediate Similarity NPC474707
0.8293 Intermediate Similarity NPC470498
0.8289 Intermediate Similarity NPC230002
0.825 Intermediate Similarity NPC135141
0.825 Intermediate Similarity NPC92796
0.8249 Intermediate Similarity NPC470497
0.8246 Intermediate Similarity NPC204565
0.8239 Intermediate Similarity NPC285469
0.8204 Intermediate Similarity NPC68354
0.8198 Intermediate Similarity NPC173028
0.8198 Intermediate Similarity NPC65215
0.8187 Intermediate Similarity NPC129721
0.8187 Intermediate Similarity NPC62749
0.8161 Intermediate Similarity NPC99666
0.8155 Intermediate Similarity NPC213468
0.8141 Intermediate Similarity NPC143872
0.8141 Intermediate Similarity NPC288838
0.8136 Intermediate Similarity NPC470499
0.8133 Intermediate Similarity NPC472123
0.8125 Intermediate Similarity NPC242209
0.8121 Intermediate Similarity NPC194411
0.8114 Intermediate Similarity NPC307963
0.8113 Intermediate Similarity NPC200214
0.8095 Intermediate Similarity NPC145885
0.8095 Intermediate Similarity NPC14113
0.8095 Intermediate Similarity NPC84827
0.8092 Intermediate Similarity NPC296527
0.8089 Intermediate Similarity NPC469811
0.8084 Intermediate Similarity NPC189812
0.8084 Intermediate Similarity NPC329688
0.8081 Intermediate Similarity NPC235684
0.8047 Intermediate Similarity NPC176199
0.8047 Intermediate Similarity NPC215795
0.8046 Intermediate Similarity NPC83111
0.8046 Intermediate Similarity NPC76748
0.8038 Intermediate Similarity NPC321911
0.8037 Intermediate Similarity NPC16667
0.8035 Intermediate Similarity NPC278434
0.8034 Intermediate Similarity NPC131887
0.8025 Intermediate Similarity NPC63545
0.8023 Intermediate Similarity NPC62510
0.8012 Intermediate Similarity NPC19679
0.8011 Intermediate Similarity NPC474177
0.8011 Intermediate Similarity NPC88315
0.8011 Intermediate Similarity NPC106937
0.8 Intermediate Similarity NPC92111
0.8 Intermediate Similarity NPC49217
0.7989 Intermediate Similarity NPC321708
0.7989 Intermediate Similarity NPC213629
0.7989 Intermediate Similarity NPC100321
0.7987 Intermediate Similarity NPC53947
0.7978 Intermediate Similarity NPC77555
0.7978 Intermediate Similarity NPC88008
0.7978 Intermediate Similarity NPC156704
0.7976 Intermediate Similarity NPC472586
0.7975 Intermediate Similarity NPC201380
0.7975 Intermediate Similarity NPC179787
0.7966 Intermediate Similarity NPC133366
0.7965 Intermediate Similarity NPC284678
0.795 Intermediate Similarity NPC207726
0.7944 Intermediate Similarity NPC106771
0.7944 Intermediate Similarity NPC23420
0.7944 Intermediate Similarity NPC205254
0.7944 Intermediate Similarity NPC213308
0.7944 Intermediate Similarity NPC303820
0.7941 Intermediate Similarity NPC472443
0.7939 Intermediate Similarity NPC42372
0.7939 Intermediate Similarity NPC470508
0.7937 Intermediate Similarity NPC470823
0.7935 Intermediate Similarity NPC314957
0.7933 Intermediate Similarity NPC473640
0.7921 Intermediate Similarity NPC13880
0.7917 Intermediate Similarity NPC34508
0.7901 Intermediate Similarity NPC52909
0.7901 Intermediate Similarity NPC475935
0.7901 Intermediate Similarity NPC94211
0.7888 Intermediate Similarity NPC141926
0.7888 Intermediate Similarity NPC325903
0.7874 Intermediate Similarity NPC94752
0.7865 Intermediate Similarity NPC326634
0.7861 Intermediate Similarity NPC165495
0.7857 Intermediate Similarity NPC476874
0.7857 Intermediate Similarity NPC193761
0.7857 Intermediate Similarity NPC476073
0.7853 Intermediate Similarity NPC477167
0.7853 Intermediate Similarity NPC473342
0.7853 Intermediate Similarity NPC324149
0.7849 Intermediate Similarity NPC314394
0.7845 Intermediate Similarity NPC315491
0.7845 Intermediate Similarity NPC45459
0.7844 Intermediate Similarity NPC154293
0.784 Intermediate Similarity NPC34844
0.784 Intermediate Similarity NPC470507
0.7836 Intermediate Similarity NPC42979
0.7829 Intermediate Similarity NPC17059
0.7824 Intermediate Similarity NPC224764
0.7816 Intermediate Similarity NPC280290
0.7815 Intermediate Similarity NPC22079
0.7811 Intermediate Similarity NPC474409
0.7805 Intermediate Similarity NPC67056
0.7803 Intermediate Similarity NPC139291
0.7803 Intermediate Similarity NPC472444
0.7803 Intermediate Similarity NPC472108
0.7802 Intermediate Similarity NPC475506
0.7799 Intermediate Similarity NPC316069
0.7798 Intermediate Similarity NPC280548
0.7797 Intermediate Similarity NPC138370
0.7792 Intermediate Similarity NPC325252

  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 NPC230869 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
0.8688 High Similarity NPD4184 Clinical (unspecified phase)
0.8639 High Similarity NPD198 Clinical (unspecified phase)
0.8545 High Similarity NPD6595 Phase 3
0.8528 High Similarity NPD5065 Approved
0.8528 High Similarity NPD482 Approved
0.8476 Intermediate Similarity NPD749 Clinical (unspecified phase)
0.8467 Intermediate Similarity NPD786 Approved
0.8355 Intermediate Similarity NPD1722 Approved
0.8333 Intermediate Similarity NPD2094 Phase 2
0.8333 Intermediate Similarity NPD2095 Phase 2
0.8333 Intermediate Similarity NPD2092 Phase 2
0.8313 Intermediate Similarity NPD2144 Approved
0.8284 Intermediate Similarity NPD2096 Phase 2
0.8284 Intermediate Similarity NPD2091 Phase 2
0.8282 Intermediate Similarity NPD5069 Clinical (unspecified phase)
0.8263 Intermediate Similarity NPD4076 Approved
0.8263 Intermediate Similarity NPD4079 Approved
0.8232 Intermediate Similarity NPD1325 Approved
0.8232 Intermediate Similarity NPD1326 Approved
0.8204 Intermediate Similarity NPD3505 Approved
0.8204 Intermediate Similarity NPD6203 Clinical (unspecified phase)
0.8204 Intermediate Similarity NPD3506 Approved
0.8166 Intermediate Similarity NPD3038 Discontinued
0.8133 Intermediate Similarity NPD750 Phase 2
0.8129 Intermediate Similarity NPD6610 Clinical (unspecified phase)
0.8117 Intermediate Similarity NPD1592 Phase 3
0.8114 Intermediate Similarity NPD1038 Approved
0.8114 Intermediate Similarity NPD5575 Clinical (unspecified phase)
0.8038 Intermediate Similarity NPD4374 Clinical (unspecified phase)
0.8038 Intermediate Similarity NPD3100 Discontinued
0.8035 Intermediate Similarity NPD8431 Approved
0.8012 Intermediate Similarity NPD5728 Clinical (unspecified phase)
0.8011 Intermediate Similarity NPD802 Phase 2
0.7989 Intermediate Similarity NPD8110 Clinical (unspecified phase)
0.7987 Intermediate Similarity NPD2172 Phase 1
0.7975 Intermediate Similarity NPD4703 Approved
0.7975 Intermediate Similarity NPD4702 Approved
0.7964 Intermediate Similarity NPD5934 Clinical (unspecified phase)
0.791 Intermediate Similarity NPD1304 Clinical (unspecified phase)
0.7877 Intermediate Similarity NPD7948 Phase 1
0.7845 Intermediate Similarity NPD484 Approved
0.7778 Intermediate Similarity NPD2837 Discontinued
0.7772 Intermediate Similarity NPD5426 Phase 3
0.7764 Intermediate Similarity NPD4462 Approved
0.7764 Intermediate Similarity NPD4463 Approved
0.7758 Intermediate Similarity NPD1403 Approved
0.7758 Intermediate Similarity NPD1404 Approved
0.7753 Intermediate Similarity NPD3404 Approved
0.7738 Intermediate Similarity NPD4640 Approved
0.7738 Intermediate Similarity NPD4639 Approved
0.7738 Intermediate Similarity NPD4638 Approved
0.7719 Intermediate Similarity NPD6375 Clinical (unspecified phase)
0.7711 Intermediate Similarity NPD972 Clinical (unspecified phase)
0.7692 Intermediate Similarity NPD7621 Clinical (unspecified phase)
0.7688 Intermediate Similarity NPD1392 Approved
0.7688 Intermediate Similarity NPD8464 Clinical (unspecified phase)
0.7676 Intermediate Similarity NPD8272 Phase 2
0.7676 Intermediate Similarity NPD5901 Discontinued
0.7665 Intermediate Similarity NPD5138 Approved
0.7665 Intermediate Similarity NPD5140 Approved
0.7661 Intermediate Similarity NPD4128 Approved
0.7634 Intermediate Similarity NPD4862 Clinical (unspecified phase)
0.7622 Intermediate Similarity NPD8072 Approved
0.761 Intermediate Similarity NPD3717 Discontinued
0.7576 Intermediate Similarity NPD276 Clinical (unspecified phase)
0.7574 Intermediate Similarity NPD2639 Approved
0.7574 Intermediate Similarity NPD2642 Approved
0.7572 Intermediate Similarity NPD4181 Approved
0.756 Intermediate Similarity NPD3323 Discontinued
0.754 Intermediate Similarity NPD7958 Clinical (unspecified phase)
0.754 Intermediate Similarity NPD7957 Phase 1
0.7531 Intermediate Similarity NPD1661 Suspended
0.7529 Intermediate Similarity NPD2640 Approved
0.7529 Intermediate Similarity NPD8386 Phase 2
0.7529 Intermediate Similarity NPD2185 Clinical (unspecified phase)
0.7529 Intermediate Similarity NPD2844 Phase 3
0.7529 Intermediate Similarity NPD2641 Approved
0.7526 Intermediate Similarity NPD7470 Discontinued
0.7514 Intermediate Similarity NPD2381 Approved
0.7514 Intermediate Similarity NPD4075 Phase 2
0.7514 Intermediate Similarity NPD2380 Approved
0.7514 Intermediate Similarity NPD2382 Approved
0.75 Intermediate Similarity NPD3825 Phase 3
0.75 Intermediate Similarity NPD1853 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD991 Phase 2
0.75 Intermediate Similarity NPD992 Clinical (unspecified phase)
0.7485 Intermediate Similarity NPD1554 Clinical (unspecified phase)
0.7484 Intermediate Similarity NPD3943 Clinical (unspecified phase)
0.7474 Intermediate Similarity NPD7809 Clinical (unspecified phase)
0.7473 Intermediate Similarity NPD8073 Approved
0.7472 Intermediate Similarity NPD706 Phase 1
0.7461 Intermediate Similarity NPD5612 Discontinued
0.746 Intermediate Similarity NPD7947 Clinical (unspecified phase)
0.7457 Intermediate Similarity NPD2928 Phase 2
0.7433 Intermediate Similarity NPD2121 Clinical (unspecified phase)
0.7427 Intermediate Similarity NPD5021 Discontinued
0.7427 Intermediate Similarity NPD5862 Discovery
0.7421 Intermediate Similarity NPD2125 Clinical (unspecified phase)
0.7414 Intermediate Similarity NPD5100 Phase 3
0.7412 Intermediate Similarity NPD5744 Clinical (unspecified phase)
0.7401 Intermediate Similarity NPD5596 Phase 2
0.7381 Intermediate Similarity NPD5255 Approved
0.7368 Intermediate Similarity NPD2189 Approved
0.7368 Intermediate Similarity NPD2187 Approved
0.7346 Intermediate Similarity NPD3813 Approved
0.7346 Intermediate Similarity NPD5254 Discontinued
0.7344 Intermediate Similarity NPD5067 Phase 2
0.7344 Intermediate Similarity NPD5066 Phase 2
0.7341 Intermediate Similarity NPD3117 Approved
0.7341 Intermediate Similarity NPD3116 Approved
0.7341 Intermediate Similarity NPD3610 Approved
0.7341 Intermediate Similarity NPD3609 Approved
0.7333 Intermediate Similarity NPD3961 Discontinued
0.7333 Intermediate Similarity NPD6141 Clinical (unspecified phase)
0.7333 Intermediate Similarity NPD3486 Clinical (unspecified phase)
0.7316 Intermediate Similarity NPD8493 Clinical (unspecified phase)
0.7316 Intermediate Similarity NPD6838 Clinical (unspecified phase)
0.7312 Intermediate Similarity NPD1768 Approved
0.7308 Intermediate Similarity NPD5912 Clinical (unspecified phase)
0.7308 Intermediate Similarity NPD5913 Phase 3
0.7306 Intermediate Similarity NPD3330 Phase 1
0.7296 Intermediate Similarity NPD1262 Discovery
0.729 Intermediate Similarity NPD3654 Approved
0.7289 Intermediate Similarity NPD6476 Clinical (unspecified phase)
0.7289 Intermediate Similarity NPD6158 Phase 2
0.7284 Intermediate Similarity NPD4637 Clinical (unspecified phase)
0.7283 Intermediate Similarity NPD7944 Discontinued
0.7282 Intermediate Similarity NPD6803 Clinical (unspecified phase)
0.7277 Intermediate Similarity NPD2510 Approved
0.7277 Intermediate Similarity NPD2509 Approved
0.7268 Intermediate Similarity NPD8488 Clinical (unspecified phase)
0.7268 Intermediate Similarity NPD1322 Clinical (unspecified phase)
0.7263 Intermediate Similarity NPD3003 Approved
0.7263 Intermediate Similarity NPD3607 Clinical (unspecified phase)
0.7263 Intermediate Similarity NPD6732 Clinical (unspecified phase)
0.7254 Intermediate Similarity NPD8013 Clinical (unspecified phase)
0.7253 Intermediate Similarity NPD6281 Approved
0.7247 Intermediate Similarity NPD3178 Discontinued
0.7244 Intermediate Similarity NPD3475 Approved
0.7244 Intermediate Similarity NPD3476 Approved
0.7238 Intermediate Similarity NPD5590 Clinical (unspecified phase)
0.7231 Intermediate Similarity NPD8112 Clinical (unspecified phase)
0.7222 Intermediate Similarity NPD7424 Clinical (unspecified phase)
0.7219 Intermediate Similarity NPD2581 Approved
0.7219 Intermediate Similarity NPD1192 Clinical (unspecified phase)
0.7219 Intermediate Similarity NPD7000 Clinical (unspecified phase)
0.7219 Intermediate Similarity NPD2582 Approved
0.7219 Intermediate Similarity NPD6999 Discontinued
0.7216 Intermediate Similarity NPD8458 Clinical (unspecified phase)
0.7216 Intermediate Similarity NPD8093 Discontinued
0.7213 Intermediate Similarity NPD4699 Discontinued
0.7212 Intermediate Similarity NPD4547 Phase 3
0.7209 Intermediate Similarity NPD926 Approved
0.7209 Intermediate Similarity NPD925 Approved
0.7204 Intermediate Similarity NPD5003 Discontinued
0.7202 Intermediate Similarity NPD7998 Clinical (unspecified phase)
0.7202 Intermediate Similarity NPD7825 Clinical (unspecified phase)
0.7198 Intermediate Similarity NPD1534 Approved
0.7193 Intermediate Similarity NPD8026 Phase 1
0.7191 Intermediate Similarity NPD6277 Clinical (unspecified phase)
0.7189 Intermediate Similarity NPD3324 Clinical (unspecified phase)
0.7189 Intermediate Similarity NPD7619 Phase 3
0.7189 Intermediate Similarity NPD7618 Phase 3
0.7186 Intermediate Similarity NPD2882 Phase 1
0.7186 Intermediate Similarity NPD3262 Approved
0.7182 Intermediate Similarity NPD4426 Clinical (unspecified phase)
0.7182 Intermediate Similarity NPD6217 Discontinued
0.7181 Intermediate Similarity NPD4601 Approved
0.7181 Intermediate Similarity NPD4600 Approved
0.7179 Intermediate Similarity NPD8094 Discontinued
0.7178 Intermediate Similarity NPD2007 Clinical (unspecified phase)
0.7178 Intermediate Similarity NPD2006 Phase 2
0.7173 Intermediate Similarity NPD7001 Phase 3
0.7169 Intermediate Similarity NPD2430 Phase 2
0.7168 Intermediate Similarity NPD424 Approved
0.7168 Intermediate Similarity NPD1248 Discontinued
0.7168 Intermediate Similarity NPD425 Approved
0.7161 Intermediate Similarity NPD2119 Approved
0.7161 Intermediate Similarity NPD2118 Approved
0.7161 Intermediate Similarity NPD9080 Approved
0.716 Intermediate Similarity NPD473 Clinical (unspecified phase)
0.716 Intermediate Similarity NPD6026 Approved
0.716 Intermediate Similarity NPD2580 Discontinued
0.7158 Intermediate Similarity NPD5117 Phase 2
0.7158 Intermediate Similarity NPD4886 Phase 2
0.7158 Intermediate Similarity NPD4499 Approved
0.7152 Intermediate Similarity NPD1683 Approved
0.7152 Intermediate Similarity NPD6148 Clinical (unspecified phase)
0.7143 Intermediate Similarity NPD2896 Discontinued
0.7143 Intermediate Similarity NPD2383 Phase 1
0.7143 Intermediate Similarity NPD2012 Clinical (unspecified phase)
0.7135 Intermediate Similarity NPD2511 Approved
0.7135 Intermediate Similarity NPD112 Approved
0.7135 Intermediate Similarity NPD8410 Clinical (unspecified phase)
0.7135 Intermediate Similarity NPD9705 Discontinued
0.7134 Intermediate Similarity NPD9207 Approved
0.7134 Intermediate Similarity NPD9206 Approved
0.7128 Intermediate Similarity NPD7594 Clinical (unspecified phase)
0.7127 Intermediate Similarity NPD6344 Clinical (unspecified phase)
0.7127 Intermediate Similarity NPD5555 Phase 1

  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