Structure

Physi-Chem Properties

Molecular Weight:  232.15
Volume:  251.998
LogP:  3.307
LogD:  3.393
LogS:  -4.185
# Rotatable Bonds:  0
TPSA:  26.3
# H-Bond Aceptor:  2
# H-Bond Donor:  0
# Rings:  3
# Heavy Atoms:  2

MedChem Properties

QED Drug-Likeness Score:  0.364
Synthetic Accessibility Score:  4.244
Fsp3:  0.667
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Rejected
GSK Rule:  Accepted
BMS Rule:  2
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.701
MDCK Permeability:  3.015323272848036e-05
Pgp-inhibitor:  0.001
Pgp-substrate:  0.0
Human Intestinal Absorption (HIA):  0.004
20% Bioavailability (F20%):  0.15
30% Bioavailability (F30%):  0.003

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.023
Plasma Protein Binding (PPB):  86.27832794189453%
Volume Distribution (VD):  1.383
Pgp-substrate:  9.927428245544434%

ADMET: Metabolism

CYP1A2-inhibitor:  0.384
CYP1A2-substrate:  0.372
CYP2C19-inhibitor:  0.447
CYP2C19-substrate:  0.491
CYP2C9-inhibitor:  0.527
CYP2C9-substrate:  0.291
CYP2D6-inhibitor:  0.065
CYP2D6-substrate:  0.368
CYP3A4-inhibitor:  0.617
CYP3A4-substrate:  0.255

ADMET: Excretion

Clearance (CL):  4.606
Half-life (T1/2):  0.312

ADMET: Toxicity

hERG Blockers:  0.022
Human Hepatotoxicity (H-HT):  0.268
Drug-inuced Liver Injury (DILI):  0.787
AMES Toxicity:  0.325
Rat Oral Acute Toxicity:  0.438
Maximum Recommended Daily Dose:  0.924
Skin Sensitization:  0.609
Carcinogencity:  0.298
Eye Corrosion:  0.743
Eye Irritation:  0.971
Respiratory Toxicity:  0.955

Download Data

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General Info & Identifiers & Properties  
Structure MOL file  
Source Organisms  
Biological Activities  
Similar NPs/Drugs  

  Natural Product: NPC226988

Natural Product ID:  NPC226988
Common Name*:   Isoalantolactone
IUPAC Name:   (3aR,4aS,8aR,9aR)-8a-methyl-3,5-dimethylidene-3a,4,4a,6,7,8,9,9a-octahydrobenzo[f][1]benzofuran-2-one
Synonyms:   Iso-Alantolacton; Isoalantolactone
Standard InCHIKey:  CVUANYCQTOGILD-QVHKTLOISA-N
Standard InCHI:  InChI=1S/C15H20O2/c1-9-5-4-6-15(3)8-13-11(7-12(9)15)10(2)14(16)17-13/h11-13H,1-2,4-8H2,3H3/t11-,12+,13-,15-/m1/s1
SMILES:  C=C1CCC[C@]2(C)C[C@@H]3[C@H](C[C@@H]12)C(=C)C(=O)O3
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL137803
PubChem CID:   73285
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0000259] Prenol lipids
        • [CHEMONTID:0001283] Terpene lactones
          • [CHEMONTID:0001543] Sesquiterpene lactones
            • [CHEMONTID:0001772] Eudesmanolides, secoeudesmanolides, and derivatives

*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
NPO17755 Inula helenium Species Asteraceae Eukaryota n.a. root n.a. PMID[10364842]
NPO17755 Inula helenium Species Asteraceae Eukaryota n.a. root n.a. PMID[12392098]
NPO40799 Bovine platelets Species n.a. n.a. n.a. n.a. n.a. PMID[1431933]
NPO25825 Saussurea lappa Species Asteraceae Eukaryota Roots n.a. n.a. PMID[14510592]
NPO23861 Inula racemosa Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[23451797]
NPO17755 Inula helenium Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[23501116]
NPO17755 Inula helenium Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[24996657]
NPO17755 Inula helenium Species Asteraceae Eukaryota n.a. root n.a. PMID[25767328]
NPO9124 Inula japonica Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[27276091]
NPO25825 Saussurea lappa Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[3572418]
NPO18609 Inula grandis Species Asteraceae Eukaryota n.a. root n.a. Database[Article]
NPO17755 Inula helenium Species Asteraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO18609 Inula grandis Species Asteraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO23861 Inula racemosa Species Asteraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO9124 Inula japonica Species Asteraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO25825 Saussurea lappa Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO18609 Inula grandis Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO23861 Inula racemosa Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO9124 Inula japonica Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO17755 Inula helenium Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO18609 Inula grandis Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO30379 Inula heienium Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO9124 Inula japonica Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO30115 Aucklandia lappa n.a. n.a. n.a. n.a. n.a. n.a. Database[TCM_Taiwan]
NPO17755 Inula helenium Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO9124 Inula japonica Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO25825 Saussurea lappa Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO18609 Inula grandis Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23861 Inula racemosa Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23330 Guatteria dumetorum Species Annonaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25374 Crotalaria sericea Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9124 Inula japonica Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24701 Schizonepeta annua Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17755 Inula helenium Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25825 Saussurea lappa Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25058 Mayetiola destructor Species Cecidomyiidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24797 Chuquiraga ulicina Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24524 Gutierrezia gymnospermoides 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

☑ 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
NPT111 Cell Line K562 Homo sapiens IC50 = 1200.0 nM PMID[533756]
NPT111 Cell Line K562 Homo sapiens GI = 38.0 % PMID[533756]
NPT111 Cell Line K562 Homo sapiens S = 50.0 % PMID[533756]
NPT111 Cell Line K562 Homo sapiens G2/M = 12.0 % PMID[533756]
NPT111 Cell Line K562 Homo sapiens Activity = 8.2 % PMID[533756]
NPT111 Cell Line K562 Homo sapiens c.v = 3.2 n.a. PMID[533756]
NPT2326 Cell Line BT-20 Homo sapiens ID50 = 1.2 uM PMID[533756]
NPT83 Cell Line MCF7 Homo sapiens ID50 = 0.6 uM PMID[533756]
NPT5297 Cell Line COLO ID50 = 2.1 uM PMID[533756]
NPT81 Cell Line A549 Homo sapiens ID50 = 0.6 uM PMID[533756]
NPT1183 Cell Line WiDr Homo sapiens ID50 = 1.4 uM PMID[533756]
NPT111 Cell Line K562 Homo sapiens ID50 = 1.2 uM PMID[533756]
NPT168 Cell Line P388 Mus musculus ID50 = 0.4 uM PMID[533756]
NPT397 Cell Line NCI-H460 Homo sapiens ID50 = 0.6 uM PMID[533756]
NPT2505 Cell Line NCI-H520 ID50 = 0.9 uM PMID[533756]
NPT108 Individual Protein Estrogen receptor alpha Homo sapiens Activity = 34.75 % PMID[533762]
NPT108 Individual Protein Estrogen receptor alpha Homo sapiens Activity = 34.7 % PMID[533762]
NPT737 Cell Line HUVEC Homo sapiens IC50 = 2.5 ug.mL-1 PMID[533764]
NPT65 Cell Line HepG2 Homo sapiens IC50 = 1.77 ug.mL-1 PMID[533764]
NPT453 Cell Line HT-1080 Homo sapiens IC50 = 0.795 ug.mL-1 PMID[533764]
NPT81 Cell Line A549 Homo sapiens IC50 = 0.38 ug.mL-1 PMID[533764]
NPT83 Cell Line MCF7 Homo sapiens IC50 = 600.0 nM PMID[533766]
NPT111 Cell Line K562 Homo sapiens IC50 = 1200.0 nM PMID[533766]
NPT168 Cell Line P388 Mus musculus IC50 = 400.0 nM PMID[533766]
NPT81 Cell Line A549 Homo sapiens IC50 = 600.0 nM PMID[533766]
NPT2505 Cell Line NCI-H520 IC50 = 900.0 nM PMID[533766]
NPT165 Cell Line HeLa Homo sapiens IC50 = 8150.0 nM PMID[533768]
NPT2 Others Unspecified ID50 = 1.1 uM PMID[533756]
NPT938 Organism Cavia porcellus Cavia porcellus Average skin reaction = 1.4 n.a. PMID[533757]
NPT938 Organism Cavia porcellus Cavia porcellus No. of sensitive = 7.0 n.a. PMID[533757]
NPT938 Organism Cavia porcellus Cavia porcellus Average skin reaction = 2.1 n.a. PMID[533757]
NPT938 Organism Cavia porcellus Cavia porcellus No. of sensitive = 8.0 n.a. PMID[533757]
NPT938 Organism Cavia porcellus Cavia porcellus Average skin reaction = 0.0 n.a. PMID[533757]
NPT938 Organism Cavia porcellus Cavia porcellus No. of sensitive = 0.0 n.a. PMID[533757]
NPT20967 CELL-LINE Platelet n.a. IC50 > 516200.0 nM PMID[533758]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. IC50 > 516500.0 nM PMID[533760]
NPT35 Others n.a. LogP = 3.42 n.a. PMID[533761]
NPT119 Organism Triticum aestivum Triticum aestivum Activity = 63.5 % PMID[533763]
NPT119 Organism Triticum aestivum Triticum aestivum Activity = 47.9 % PMID[533763]
NPT119 Organism Triticum aestivum Triticum aestivum Activity = 51.7 % PMID[533763]
NPT119 Organism Triticum aestivum Triticum aestivum Activity = 53.7 % PMID[533763]
NPT119 Organism Triticum aestivum Triticum aestivum Activity = 100.4 % PMID[533763]
NPT119 Organism Triticum aestivum Triticum aestivum Activity = 96.0 % PMID[533763]
NPT119 Organism Triticum aestivum Triticum aestivum Activity = 102.0 % PMID[533763]
NPT119 Organism Triticum aestivum Triticum aestivum Activity = 100.0 % PMID[533763]
NPT119 Organism Triticum aestivum Triticum aestivum Activity = 83.9 % PMID[533763]
NPT119 Organism Triticum aestivum Triticum aestivum Activity = 76.9 % PMID[533763]
NPT119 Organism Triticum aestivum Triticum aestivum Activity = 63.7 % PMID[533763]
NPT119 Organism Triticum aestivum Triticum aestivum Activity = 46.0 % PMID[533763]
NPT119 Organism Triticum aestivum Triticum aestivum Activity = 101.2 % PMID[533763]
NPT119 Organism Triticum aestivum Triticum aestivum Activity = 99.1 % PMID[533763]
NPT119 Organism Triticum aestivum Triticum aestivum Activity = 97.4 % PMID[533763]
NPT119 Organism Triticum aestivum Triticum aestivum Activity = 100.7 % PMID[533763]
NPT119 Organism Triticum aestivum Triticum aestivum Activity = 82.5 % PMID[533763]
NPT119 Organism Triticum aestivum Triticum aestivum Activity = 84.6 % PMID[533763]
NPT119 Organism Triticum aestivum Triticum aestivum Activity = 76.1 % PMID[533763]
NPT119 Organism Triticum aestivum Triticum aestivum Activity = 25.0 % PMID[533763]
NPT119 Organism Triticum aestivum Triticum aestivum Activity = 94.0 % PMID[533763]
NPT119 Organism Triticum aestivum Triticum aestivum Activity = 106.7 % PMID[533763]
NPT778 Organism Sitophilus oryzae Sitophilus oryzae LC50 = 610.51 ug/g PMID[533763]
NPT778 Organism Sitophilus oryzae Sitophilus oryzae LC50 = 655.31 ug/g PMID[533763]
NPT778 Organism Sitophilus oryzae Sitophilus oryzae LC50 = 707.21 ug/g PMID[533763]
NPT778 Organism Sitophilus oryzae Sitophilus oryzae LC50 = 1234.57 ug/g PMID[533763]
NPT778 Organism Sitophilus oryzae Sitophilus oryzae mortality = 100.0 % PMID[533763]
NPT778 Organism Sitophilus oryzae Sitophilus oryzae mortality = 86.54 % PMID[533763]
NPT778 Organism Sitophilus oryzae Sitophilus oryzae mortality = 76.19 % PMID[533763]
NPT778 Organism Sitophilus oryzae Sitophilus oryzae mortality = 74.36 % PMID[533763]
NPT778 Organism Sitophilus oryzae Sitophilus oryzae mortality = 69.23 % PMID[533763]
NPT778 Organism Sitophilus oryzae Sitophilus oryzae mortality = 64.28 % PMID[533763]
NPT778 Organism Sitophilus oryzae Sitophilus oryzae mortality = 42.86 % PMID[533763]
NPT778 Organism Sitophilus oryzae Sitophilus oryzae mortality = 58.97 % PMID[533763]
NPT778 Organism Sitophilus oryzae Sitophilus oryzae mortality = 56.41 % PMID[533763]
NPT778 Organism Sitophilus oryzae Sitophilus oryzae mortality = 55.38 % PMID[533763]
NPT778 Organism Sitophilus oryzae Sitophilus oryzae mortality = 33.33 % PMID[533763]
NPT778 Organism Sitophilus oryzae Sitophilus oryzae mortality = 35.91 % PMID[533763]
NPT778 Organism Sitophilus oryzae Sitophilus oryzae mortality = 30.77 % PMID[533763]
NPT778 Organism Sitophilus oryzae Sitophilus oryzae mortality = 23.81 % PMID[533763]
NPT778 Organism Sitophilus oryzae Sitophilus oryzae mortality = 19.04 % PMID[533763]
NPT778 Organism Sitophilus oryzae Sitophilus oryzae mortality = 17.95 % PMID[533763]
NPT778 Organism Sitophilus oryzae Sitophilus oryzae mortality = 16.67 % PMID[533763]
NPT778 Organism Sitophilus oryzae Sitophilus oryzae mortality = 11.9 % PMID[533763]
NPT778 Organism Sitophilus oryzae Sitophilus oryzae Activity = 13.22 % PMID[533763]
NPT778 Organism Sitophilus oryzae Sitophilus oryzae Activity = 12.13 % PMID[533763]
NPT778 Organism Sitophilus oryzae Sitophilus oryzae Activity = 12.41 % PMID[533763]
NPT778 Organism Sitophilus oryzae Sitophilus oryzae Activity = 12.87 % PMID[533763]
NPT840 Individual Protein Transcriptional activator Myb Gallus gallus IC50 = 19230.92 nM PMID[533765]
NPT27 Others Unspecified IC50 > 30000.0 nM PMID[533765]
NPT840 Individual Protein Transcriptional activator Myb Gallus gallus IC50 = 19230.0 nM PMID[533765]
NPT25209 PROTEIN-PROTEIN INTERACTION Transforming growth factor beta-1 proprotein/Mothers against decapentaplegic homolog 3 Mus musculus Inhibition = -35.36 % PMID[533767]

☑ 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 NPC226988 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
0.9383 High Similarity NPC175293
0.9383 High Similarity NPC305029
0.9383 High Similarity NPC181103
0.9367 High Similarity NPC194637
0.9359 High Similarity NPC38642
0.9259 High Similarity NPC9231
0.9259 High Similarity NPC85698
0.925 High Similarity NPC219011
0.925 High Similarity NPC470011
0.9211 High Similarity NPC92489
0.9157 High Similarity NPC116620
0.9048 High Similarity NPC475776
0.9024 High Similarity NPC477920
0.8929 High Similarity NPC73995
0.8916 High Similarity NPC470012
0.8824 High Similarity NPC152467
0.881 High Similarity NPC215831
0.8795 High Similarity NPC185638
0.8765 High Similarity NPC178676
0.8736 High Similarity NPC148000
0.8736 High Similarity NPC469596
0.8736 High Similarity NPC24861
0.8736 High Similarity NPC225474
0.8721 High Similarity NPC186363
0.8721 High Similarity NPC233345
0.8642 High Similarity NPC475951
0.8642 High Similarity NPC223330
0.8642 High Similarity NPC209318
0.8636 High Similarity NPC259042
0.8636 High Similarity NPC56369
0.8636 High Similarity NPC157686
0.8636 High Similarity NPC90014
0.8588 High Similarity NPC277771
0.8554 High Similarity NPC97505
0.8539 High Similarity NPC473964
0.8539 High Similarity NPC93245
0.8539 High Similarity NPC307164
0.8523 High Similarity NPC474841
0.8523 High Similarity NPC471446
0.8523 High Similarity NPC473434
0.8506 High Similarity NPC49420
0.8488 Intermediate Similarity NPC288699
0.8452 Intermediate Similarity NPC110405
0.8444 Intermediate Similarity NPC136781
0.8444 Intermediate Similarity NPC474921
0.8444 Intermediate Similarity NPC473963
0.8434 Intermediate Similarity NPC22611
0.8427 Intermediate Similarity NPC183012
0.8395 Intermediate Similarity NPC263951
0.8372 Intermediate Similarity NPC477128
0.8352 Intermediate Similarity NPC473155
0.8352 Intermediate Similarity NPC252295
0.8333 Intermediate Similarity NPC139566
0.8315 Intermediate Similarity NPC477130
0.8315 Intermediate Similarity NPC477129
0.8315 Intermediate Similarity NPC66581
0.8293 Intermediate Similarity NPC195424
0.8276 Intermediate Similarity NPC194642
0.8272 Intermediate Similarity NPC35574
0.8261 Intermediate Similarity NPC47024
0.8261 Intermediate Similarity NPC470906
0.8261 Intermediate Similarity NPC476303
0.8235 Intermediate Similarity NPC177932
0.8202 Intermediate Similarity NPC475700
0.8193 Intermediate Similarity NPC475665
0.8182 Intermediate Similarity NPC158488
0.8172 Intermediate Similarity NPC475958
0.8161 Intermediate Similarity NPC226863
0.8152 Intermediate Similarity NPC476807
0.8152 Intermediate Similarity NPC476806
0.8152 Intermediate Similarity NPC216478
0.814 Intermediate Similarity NPC250981
0.814 Intermediate Similarity NPC6979
0.814 Intermediate Similarity NPC471042
0.8132 Intermediate Similarity NPC228766
0.8132 Intermediate Similarity NPC165528
0.8132 Intermediate Similarity NPC284518
0.8118 Intermediate Similarity NPC30486
0.8118 Intermediate Similarity NPC159635
0.8111 Intermediate Similarity NPC470697
0.8095 Intermediate Similarity NPC258153
0.8095 Intermediate Similarity NPC476458
0.8095 Intermediate Similarity NPC186276
0.809 Intermediate Similarity NPC72845
0.8068 Intermediate Similarity NPC50488
0.8068 Intermediate Similarity NPC474396
0.8043 Intermediate Similarity NPC474343
0.8022 Intermediate Similarity NPC280877
0.8 Intermediate Similarity NPC474185
0.8 Intermediate Similarity NPC139692
0.8 Intermediate Similarity NPC475657
0.8 Intermediate Similarity NPC476237
0.8 Intermediate Similarity NPC61442
0.8 Intermediate Similarity NPC243347
0.8 Intermediate Similarity NPC176883
0.8 Intermediate Similarity NPC147272
0.8 Intermediate Similarity NPC254202
0.8 Intermediate Similarity NPC470948
0.8 Intermediate Similarity NPC170862
0.7978 Intermediate Similarity NPC212679
0.7978 Intermediate Similarity NPC220454
0.7978 Intermediate Similarity NPC469595
0.7978 Intermediate Similarity NPC8062
0.7976 Intermediate Similarity NPC47635
0.7952 Intermediate Similarity NPC471475
0.7931 Intermediate Similarity NPC329692
0.7927 Intermediate Similarity NPC189206
0.7917 Intermediate Similarity NPC477127
0.7912 Intermediate Similarity NPC224410
0.7912 Intermediate Similarity NPC250075
0.7912 Intermediate Similarity NPC57117
0.7912 Intermediate Similarity NPC100257
0.7907 Intermediate Similarity NPC96055
0.7907 Intermediate Similarity NPC475509
0.7907 Intermediate Similarity NPC130966
0.7901 Intermediate Similarity NPC39362
0.7895 Intermediate Similarity NPC164551
0.7882 Intermediate Similarity NPC200513
0.7882 Intermediate Similarity NPC471159
0.7882 Intermediate Similarity NPC123880
0.7865 Intermediate Similarity NPC11611
0.7865 Intermediate Similarity NPC471043
0.7865 Intermediate Similarity NPC168131
0.7857 Intermediate Similarity NPC293418
0.7857 Intermediate Similarity NPC170038
0.7857 Intermediate Similarity NPC73052
0.7857 Intermediate Similarity NPC290508
0.7857 Intermediate Similarity NPC6823
0.7849 Intermediate Similarity NPC84335
0.7849 Intermediate Similarity NPC38530
0.7849 Intermediate Similarity NPC110937
0.7841 Intermediate Similarity NPC476932
0.7826 Intermediate Similarity NPC210214
0.7816 Intermediate Similarity NPC189311
0.7816 Intermediate Similarity NPC98270
0.7816 Intermediate Similarity NPC52628
0.7812 Intermediate Similarity NPC99510
0.7812 Intermediate Similarity NPC72842
0.7805 Intermediate Similarity NPC476601
0.7805 Intermediate Similarity NPC41017
0.7802 Intermediate Similarity NPC294263
0.7791 Intermediate Similarity NPC193198
0.7791 Intermediate Similarity NPC471037
0.7789 Intermediate Similarity NPC308824
0.7789 Intermediate Similarity NPC242666
0.7778 Intermediate Similarity NPC161638
0.7778 Intermediate Similarity NPC475965
0.7778 Intermediate Similarity NPC153853
0.7778 Intermediate Similarity NPC474842
0.7778 Intermediate Similarity NPC320537
0.7778 Intermediate Similarity NPC143979
0.7766 Intermediate Similarity NPC176845
0.7755 Intermediate Similarity NPC110496
0.7755 Intermediate Similarity NPC284732
0.7755 Intermediate Similarity NPC78966
0.7753 Intermediate Similarity NPC474845
0.7753 Intermediate Similarity NPC136879
0.7753 Intermediate Similarity NPC477302
0.7742 Intermediate Similarity NPC472362
0.7742 Intermediate Similarity NPC242848
0.7742 Intermediate Similarity NPC13949
0.7742 Intermediate Similarity NPC134072
0.7742 Intermediate Similarity NPC104568
0.7742 Intermediate Similarity NPC154526
0.7742 Intermediate Similarity NPC472363
0.7742 Intermediate Similarity NPC234993
0.7738 Intermediate Similarity NPC118987
0.7732 Intermediate Similarity NPC283850
0.7732 Intermediate Similarity NPC189616
0.7727 Intermediate Similarity NPC472505
0.7717 Intermediate Similarity NPC38830
0.7717 Intermediate Similarity NPC84893
0.7711 Intermediate Similarity NPC316500
0.7711 Intermediate Similarity NPC41780
0.7711 Intermediate Similarity NPC187568
0.7711 Intermediate Similarity NPC474433
0.7708 Intermediate Similarity NPC476081
0.7692 Intermediate Similarity NPC65513
0.7692 Intermediate Similarity NPC469868
0.7692 Intermediate Similarity NPC250753
0.7692 Intermediate Similarity NPC470230
0.7684 Intermediate Similarity NPC471413
0.7684 Intermediate Similarity NPC470761
0.7684 Intermediate Similarity NPC476299
0.7684 Intermediate Similarity NPC473219
0.7684 Intermediate Similarity NPC474012
0.7684 Intermediate Similarity NPC201406
0.7677 Intermediate Similarity NPC189075
0.7677 Intermediate Similarity NPC275539
0.7677 Intermediate Similarity NPC37628
0.7667 Intermediate Similarity NPC77001
0.7667 Intermediate Similarity NPC253618
0.7667 Intermediate Similarity NPC218927
0.7667 Intermediate Similarity NPC206001
0.766 Intermediate Similarity NPC73911
0.766 Intermediate Similarity NPC10057
0.766 Intermediate Similarity NPC151681
0.766 Intermediate Similarity NPC292133
0.766 Intermediate Similarity NPC474395
0.766 Intermediate Similarity NPC132753

  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 NPC226988 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
0.8235 Intermediate Similarity NPD1694 Approved
0.7882 Intermediate Similarity NPD4752 Clinical (unspecified phase)
0.7579 Intermediate Similarity NPD4225 Approved
0.75 Intermediate Similarity NPD8035 Phase 2
0.75 Intermediate Similarity NPD8034 Phase 2
0.7416 Intermediate Similarity NPD7520 Clinical (unspecified phase)
0.734 Intermediate Similarity NPD7900 Approved
0.734 Intermediate Similarity NPD7901 Clinical (unspecified phase)
0.7333 Intermediate Similarity NPD7334 Approved
0.7333 Intermediate Similarity NPD5330 Approved
0.7333 Intermediate Similarity NPD7146 Approved
0.7333 Intermediate Similarity NPD7521 Approved
0.7333 Intermediate Similarity NPD6409 Approved
0.7333 Intermediate Similarity NPD6684 Approved
0.7253 Intermediate Similarity NPD3573 Approved
0.7234 Intermediate Similarity NPD6399 Phase 3
0.7216 Intermediate Similarity NPD7638 Approved
0.7174 Intermediate Similarity NPD6903 Approved
0.7174 Intermediate Similarity NPD7513 Clinical (unspecified phase)
0.7158 Intermediate Similarity NPD7748 Approved
0.7143 Intermediate Similarity NPD7640 Approved
0.7143 Intermediate Similarity NPD3618 Phase 1
0.7143 Intermediate Similarity NPD7639 Approved
0.7129 Intermediate Similarity NPD6008 Approved
0.7113 Intermediate Similarity NPD7902 Approved
0.7083 Intermediate Similarity NPD6356 Clinical (unspecified phase)
0.6989 Remote Similarity NPD5737 Approved
0.6989 Remote Similarity NPD6672 Approved
0.6979 Remote Similarity NPD6001 Approved
0.6947 Remote Similarity NPD5693 Phase 1
0.6947 Remote Similarity NPD7515 Phase 2
0.6944 Remote Similarity NPD7115 Discovery
0.6893 Remote Similarity NPD5954 Clinical (unspecified phase)
0.6889 Remote Similarity NPD3667 Approved
0.6771 Remote Similarity NPD6079 Approved
0.6739 Remote Similarity NPD3668 Phase 3
0.6739 Remote Similarity NPD4786 Approved
0.6737 Remote Similarity NPD5328 Approved
0.6737 Remote Similarity NPD1695 Approved
0.6735 Remote Similarity NPD1698 Clinical (unspecified phase)
0.6731 Remote Similarity NPD5697 Approved
0.6706 Remote Similarity NPD5777 Approved
0.6698 Remote Similarity NPD5955 Clinical (unspecified phase)
0.6667 Remote Similarity NPD6881 Approved
0.6667 Remote Similarity NPD6011 Approved
0.6667 Remote Similarity NPD6899 Approved
0.6667 Remote Similarity NPD5207 Approved
0.6667 Remote Similarity NPD7632 Discontinued
0.6667 Remote Similarity NPD1733 Clinical (unspecified phase)
0.6636 Remote Similarity NPD6649 Approved
0.6636 Remote Similarity NPD6650 Approved
0.6635 Remote Similarity NPD6402 Approved
0.6635 Remote Similarity NPD7128 Approved
0.6635 Remote Similarity NPD5739 Approved
0.6635 Remote Similarity NPD6675 Approved
0.6632 Remote Similarity NPD5208 Approved
0.663 Remote Similarity NPD4788 Approved
0.6604 Remote Similarity NPD4061 Clinical (unspecified phase)
0.6604 Remote Similarity NPD6014 Approved
0.6604 Remote Similarity NPD6372 Approved
0.6604 Remote Similarity NPD6013 Approved
0.6604 Remote Similarity NPD6373 Approved
0.6604 Remote Similarity NPD6012 Approved
0.6596 Remote Similarity NPD6098 Approved
0.6591 Remote Similarity NPD6117 Approved
0.6571 Remote Similarity NPD5701 Approved
0.6562 Remote Similarity NPD6051 Approved
0.6562 Remote Similarity NPD6904 Approved
0.6562 Remote Similarity NPD6673 Approved
0.6562 Remote Similarity NPD6080 Approved
0.6559 Remote Similarity NPD3666 Approved
0.6559 Remote Similarity NPD3133 Approved
0.6559 Remote Similarity NPD3665 Phase 1
0.6552 Remote Similarity NPD6113 Clinical (unspecified phase)
0.6542 Remote Similarity NPD6883 Approved
0.6542 Remote Similarity NPD7102 Approved
0.6542 Remote Similarity NPD7290 Approved
0.6535 Remote Similarity NPD5696 Approved
0.6531 Remote Similarity NPD4202 Approved
0.6517 Remote Similarity NPD6116 Phase 1
0.6509 Remote Similarity NPD5345 Clinical (unspecified phase)
0.6509 Remote Similarity NPD6686 Approved
0.6509 Remote Similarity NPD7320 Approved
0.65 Remote Similarity NPD5220 Clinical (unspecified phase)
0.65 Remote Similarity NPD5222 Approved
0.65 Remote Similarity NPD4697 Phase 3
0.65 Remote Similarity NPD5221 Approved
0.6481 Remote Similarity NPD6617 Approved
0.6481 Remote Similarity NPD8130 Phase 1
0.6481 Remote Similarity NPD6847 Approved
0.6481 Remote Similarity NPD6869 Approved
0.6477 Remote Similarity NPD8039 Approved
0.6444 Remote Similarity NPD6115 Approved
0.6444 Remote Similarity NPD6114 Approved
0.6444 Remote Similarity NPD6118 Approved
0.6444 Remote Similarity NPD6697 Approved
0.6436 Remote Similarity NPD6084 Phase 2
0.6436 Remote Similarity NPD6083 Phase 2
0.6436 Remote Similarity NPD5173 Approved
0.6422 Remote Similarity NPD8297 Approved
0.6422 Remote Similarity NPD6882 Approved
0.6421 Remote Similarity NPD3574 Clinical (unspecified phase)
0.64 Remote Similarity NPD5695 Phase 3
0.6364 Remote Similarity NPD8133 Approved
0.6346 Remote Similarity NPD5211 Phase 2
0.6337 Remote Similarity NPD5349 Clinical (unspecified phase)
0.633 Remote Similarity NPD6401 Clinical (unspecified phase)
0.6327 Remote Similarity NPD5785 Approved
0.6327 Remote Similarity NPD5692 Phase 3
0.6311 Remote Similarity NPD5285 Approved
0.6311 Remote Similarity NPD4696 Approved
0.6311 Remote Similarity NPD5286 Approved
0.6304 Remote Similarity NPD4695 Discontinued
0.6292 Remote Similarity NPD3702 Approved
0.6279 Remote Similarity NPD3700 Clinical (unspecified phase)
0.6279 Remote Similarity NPD3699 Clinical (unspecified phase)
0.6275 Remote Similarity NPD4755 Approved
0.6263 Remote Similarity NPD5694 Approved
0.6263 Remote Similarity NPD6411 Approved
0.6263 Remote Similarity NPD6050 Approved
0.6261 Remote Similarity NPD6291 Clinical (unspecified phase)
0.625 Remote Similarity NPD6274 Approved
0.625 Remote Similarity NPD6868 Approved
0.625 Remote Similarity NPD5223 Approved
0.6226 Remote Similarity NPD5141 Approved
0.6216 Remote Similarity NPD4632 Approved
0.6207 Remote Similarity NPD4691 Approved
0.6195 Remote Similarity NPD6317 Approved
0.619 Remote Similarity NPD4633 Approved
0.619 Remote Similarity NPD5225 Approved
0.619 Remote Similarity NPD5226 Approved
0.619 Remote Similarity NPD5224 Approved
0.617 Remote Similarity NPD4223 Phase 3
0.617 Remote Similarity NPD5209 Approved
0.617 Remote Similarity NPD4221 Approved
0.6163 Remote Similarity NPD229 Approved
0.6154 Remote Similarity NPD4700 Approved
0.614 Remote Similarity NPD6313 Approved
0.614 Remote Similarity NPD6335 Approved
0.614 Remote Similarity NPD6314 Approved
0.6136 Remote Similarity NPD4808 Clinical (unspecified phase)
0.6136 Remote Similarity NPD4809 Clinical (unspecified phase)
0.6132 Remote Similarity NPD6052 Approved
0.6132 Remote Similarity NPD5175 Approved
0.6132 Remote Similarity NPD5174 Approved
0.6118 Remote Similarity NPD4224 Phase 2
0.6111 Remote Similarity NPD3703 Phase 2
0.61 Remote Similarity NPD5281 Approved
0.61 Remote Similarity NPD5284 Approved
0.6098 Remote Similarity NPD1145 Discontinued
0.6092 Remote Similarity NPD4137 Phase 3
0.6087 Remote Similarity NPD7101 Approved
0.6087 Remote Similarity NPD7100 Approved
0.6087 Remote Similarity NPD3617 Approved
0.6082 Remote Similarity NPD4519 Discontinued
0.6082 Remote Similarity NPD4623 Approved
0.6082 Remote Similarity NPD5279 Phase 3
0.6078 Remote Similarity NPD4629 Approved
0.6078 Remote Similarity NPD5210 Approved
0.6061 Remote Similarity NPD5764 Clinical (unspecified phase)
0.6061 Remote Similarity NPD7285 Clinical (unspecified phase)
0.6061 Remote Similarity NPD4753 Phase 2
0.6061 Remote Similarity NPD6101 Approved
0.6053 Remote Similarity NPD6009 Approved
0.605 Remote Similarity NPD7507 Approved
0.6044 Remote Similarity NPD3701 Clinical (unspecified phase)
0.6042 Remote Similarity NPD4197 Approved
0.604 Remote Similarity NPD5778 Approved
0.604 Remote Similarity NPD5779 Approved
0.6034 Remote Similarity NPD6319 Approved
0.6023 Remote Similarity NPD4747 Approved
0.6022 Remote Similarity NPD7645 Phase 2
0.6019 Remote Similarity NPD7732 Phase 3
0.6 Remote Similarity NPD3171 Clinical (unspecified phase)
0.6 Remote Similarity NPD8132 Clinical (unspecified phase)
0.6 Remote Similarity NPD4058 Approved
0.5983 Remote Similarity NPD5983 Phase 2
0.5981 Remote Similarity NPD4754 Approved
0.5979 Remote Similarity NPD5329 Approved
0.5966 Remote Similarity NPD7492 Approved
0.5963 Remote Similarity NPD6614 Approved
0.5957 Remote Similarity NPD7525 Registered
0.5941 Remote Similarity NPD7637 Suspended
0.5934 Remote Similarity NPD7339 Approved
0.5934 Remote Similarity NPD6942 Approved
0.5922 Remote Similarity NPD5654 Approved
0.5918 Remote Similarity NPD5205 Approved
0.5918 Remote Similarity NPD5690 Phase 2
0.5918 Remote Similarity NPD4693 Phase 3
0.5918 Remote Similarity NPD4689 Approved
0.5918 Remote Similarity NPD4688 Approved
0.5918 Remote Similarity NPD4690 Approved
0.5918 Remote Similarity NPD4138 Approved
0.5917 Remote Similarity NPD6616 Approved
0.5909 Remote Similarity NPD5168 Approved
0.5909 Remote Similarity NPD5128 Approved
0.5909 Remote Similarity NPD4729 Approved
0.5909 Remote Similarity NPD4730 Approved
0.5909 Remote Similarity NPD3698 Phase 2
0.5902 Remote Similarity NPD7319 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