Structure

Physi-Chem Properties

Molecular Weight:  164.12
Volume:  191.137
LogP:  2.472
LogD:  2.568
LogS:  -3.422
# Rotatable Bonds:  3
TPSA:  17.07
# H-Bond Aceptor:  1
# H-Bond Donor:  0
# Rings:  1
# Heavy Atoms:  1

MedChem Properties

QED Drug-Likeness Score:  0.586
Synthetic Accessibility Score:  3.11
Fsp3:  0.545
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:  -4.594
MDCK Permeability:  2.787312405416742e-05
Pgp-inhibitor:  0.027
Pgp-substrate:  0.007
Human Intestinal Absorption (HIA):  0.009
20% Bioavailability (F20%):  0.942
30% Bioavailability (F30%):  0.924

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.908
Plasma Protein Binding (PPB):  80.05655670166016%
Volume Distribution (VD):  0.745
Pgp-substrate:  18.82586097717285%

ADMET: Metabolism

CYP1A2-inhibitor:  0.741
CYP1A2-substrate:  0.903
CYP2C19-inhibitor:  0.484
CYP2C19-substrate:  0.77
CYP2C9-inhibitor:  0.099
CYP2C9-substrate:  0.606
CYP2D6-inhibitor:  0.481
CYP2D6-substrate:  0.831
CYP3A4-inhibitor:  0.05
CYP3A4-substrate:  0.316

ADMET: Excretion

Clearance (CL):  8.942
Half-life (T1/2):  0.907

ADMET: Toxicity

hERG Blockers:  0.027
Human Hepatotoxicity (H-HT):  0.146
Drug-inuced Liver Injury (DILI):  0.175
AMES Toxicity:  0.12
Rat Oral Acute Toxicity:  0.26
Maximum Recommended Daily Dose:  0.417
Skin Sensitization:  0.627
Carcinogencity:  0.776
Eye Corrosion:  0.033
Eye Irritation:  0.424
Respiratory Toxicity:  0.594

Download Data

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Structure MOL file  
Source Organisms  
Biological Activities  
Similar NPs/Drugs  

  Natural Product: NPC100380

Natural Product ID:  NPC100380
Common Name*:   Cis-Jasmone
IUPAC Name:   3-methyl-2-[(Z)-pent-2-enyl]cyclopent-2-en-1-one
Synonyms:  
Standard InCHIKey:  XMLSXPIVAXONDL-PLNGDYQASA-N
Standard InCHI:  InChI=1S/C11H16O/c1-3-4-5-6-10-9(2)7-8-11(10)12/h4-5H,3,6-8H2,1-2H3/b5-4-
SMILES:  CC/C=CCC1=C(C)CCC1=O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL2251602
PubChem CID:   1549018
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0004603] Organic oxygen compounds
      • [CHEMONTID:0000323] Organooxygen compounds
        • [CHEMONTID:0001831] Carbonyl compounds
          • [CHEMONTID:0000118] Ketones
            • [CHEMONTID:0003487] Cyclic ketones

*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
NPO1515 Lonicera japonica Species Caprifoliaceae Eukaryota Flowers n.a. n.a. DOI[10.1002/elan.200403102]
NPO1515 Lonicera japonica Species Caprifoliaceae Eukaryota Flowers n.a. n.a. DOI[10.1016/j.foodchem.2012.02.124]
NPO8258 Camellia sinensis Species Theaceae Eukaryota n.a. n.a. n.a. DOI[10.1016/j.foodchem.2013.08.121]
NPO4391 Hypericum perforatum Species Hypericaceae Eukaryota n.a. n.a. n.a. DOI[10.1078/0176-1617-00195]
NPO4391 Hypericum perforatum Species Hypericaceae Eukaryota n.a. n.a. n.a. PMID[10757735]
NPO1515 Lonicera japonica Species Caprifoliaceae Eukaryota Flowers n.a. n.a. PMID[11077184]
NPO14579 Mentha spicata Species Lamiaceae Eukaryota n.a. n.a. n.a. PMID[12776552]
NPO4391 Hypericum perforatum Species Hypericaceae Eukaryota n.a. n.a. n.a. PMID[14735439]
NPO4391 Hypericum perforatum Species Hypericaceae Eukaryota n.a. callus n.a. PMID[15715262]
NPO8258 Camellia sinensis Species Theaceae Eukaryota Flowers n.a. n.a. PMID[16180814]
NPO8258 Camellia sinensis Species Theaceae Eukaryota seeds Shizuoka prefecture, Japan n.a. PMID[16499314]
NPO1515 Lonicera japonica Species Caprifoliaceae Eukaryota Flowers n.a. n.a. PMID[17328234]
NPO8258 Camellia sinensis Species Theaceae Eukaryota n.a. n.a. n.a. PMID[18068204]
NPO4391 Hypericum perforatum Species Hypericaceae Eukaryota n.a. n.a. n.a. PMID[18220354]
NPO1515 Lonicera japonica Species Caprifoliaceae Eukaryota Flower buds n.a. n.a. PMID[18321056]
NPO8258 Camellia sinensis Species Theaceae Eukaryota n.a. n.a. n.a. PMID[21434603]
NPO1515 Lonicera japonica Species Caprifoliaceae Eukaryota n.a. flower n.a. PMID[21804227]
NPO8258 Camellia sinensis Species Theaceae Eukaryota n.a. flower n.a. PMID[21922925]
NPO8258 Camellia sinensis Species Theaceae Eukaryota flower buds n.a. n.a. PMID[21925888]
NPO1515 Lonicera japonica Species Caprifoliaceae Eukaryota flower buds Henan province, China 2005-MAY PMID[21942812]
NPO1515 Lonicera japonica Species Caprifoliaceae Eukaryota n.a. flower bud n.a. PMID[21942812]
NPO8258 Camellia sinensis Species Theaceae Eukaryota leaves n.a. n.a. PMID[22377672]
NPO8258 Camellia sinensis Species Theaceae Eukaryota n.a. leaf n.a. PMID[23265489]
NPO1515 Lonicera japonica Species Caprifoliaceae Eukaryota n.a. leaf n.a. PMID[23265495]
NPO8258 Camellia sinensis Species Theaceae Eukaryota Leaves Bandung, West Java, Indonesia PMID[23621359]
NPO1515 Lonicera japonica Species Caprifoliaceae Eukaryota Flower buds n.a. n.a. PMID[24279769]
NPO4391 Hypericum perforatum Species Hypericaceae Eukaryota n.a. n.a. n.a. PMID[28445039]
NPO4391 Hypericum perforatum Species Hypericaceae Eukaryota Roots n.a. n.a. PMID[30024167]
NPO21355 Elsholtzia ciliata Species Lamiaceae Eukaryota Aerial Parts n.a. n.a. PMID[32991171]
NPO8258 Camellia sinensis Species Theaceae Eukaryota Shoot n.a. n.a. Database[FooDB]
NPO8258 Camellia sinensis Species Theaceae Eukaryota Cotyledon n.a. n.a. Database[FooDB]
NPO8258 Camellia sinensis Species Theaceae Eukaryota Stem n.a. n.a. Database[FooDB]
NPO14579 Mentha spicata Species Lamiaceae Eukaryota Leaf n.a. n.a. Database[FooDB]
NPO14579 Mentha spicata Species Lamiaceae Eukaryota n.a. n.a. Database[FooDB]
NPO23256 Mentha arvensis Species Lamiaceae Eukaryota Leaf n.a. n.a. Database[FooDB]
NPO22233 Allium schoenoprasum Species Amaryllidaceae Eukaryota Leaf n.a. n.a. Database[FooDB]
NPO26637 Mentha aquatica Species Lamiaceae Eukaryota Leaf n.a. n.a. Database[FooDB]
NPO14579 Mentha spicata Species Lamiaceae Eukaryota n.a. n.a. Database[FooDB]
NPO8258 Camellia sinensis Species Theaceae Eukaryota Leaf n.a. n.a. Database[FooDB]
NPO22233 Allium schoenoprasum Species Amaryllidaceae Eukaryota n.a. n.a. Database[FooDB]
NPO22233 Allium schoenoprasum Species Amaryllidaceae Eukaryota Leaf Essent. Oil n.a. n.a. Database[FooDB]
NPO8258 Camellia sinensis Species Theaceae Eukaryota n.a. n.a. Database[FooDB]
NPO8258 Camellia sinensis Species Theaceae Eukaryota Leaf Essent. Oil n.a. n.a. Database[FooDB]
NPO14579 Mentha spicata Species Lamiaceae Eukaryota Plant n.a. n.a. Database[FooDB]
NPO23256 Mentha arvensis Species Lamiaceae Eukaryota Plant n.a. n.a. Database[FooDB]
NPO26637 Mentha aquatica Species Lamiaceae Eukaryota Plant n.a. n.a. Database[FooDB]
NPO8258 Camellia sinensis Species Theaceae Eukaryota Plant n.a. n.a. Database[FooDB]
NPO8258 Camellia sinensis Species Theaceae Eukaryota Seed n.a. n.a. Database[FooDB]
NPO8258 Camellia sinensis Species Theaceae Eukaryota Seed Oil n.a. n.a. Database[FooDB]
NPO14579 Mentha spicata Species Lamiaceae Eukaryota Shoot n.a. n.a. Database[FooDB]
NPO8258 Camellia sinensis Species Theaceae Eukaryota n.a. n.a. Database[FooDB]
NPO26637 Mentha aquatica Species Lamiaceae Eukaryota Shoot n.a. n.a. Database[FooDB]
NPO22233 Allium schoenoprasum Species Amaryllidaceae Eukaryota n.a. n.a. Database[FooDB]
NPO21355 Elsholtzia ciliata Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO4391 Hypericum perforatum Species Hypericaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO14579 Mentha spicata Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO22233 Allium schoenoprasum Species Amaryllidaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO8258 Camellia sinensis Species Theaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO1515 Lonicera japonica Species Caprifoliaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO18046 Mosla chinensis Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO14579 Mentha spicata Species Lamiaceae Eukaryota n.a. n.a. Database[Phenol-Explorer]
NPO4391 Hypericum perforatum Species Hypericaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO8258 Camellia sinensis Species Theaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO18046 Mosla chinensis Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO13857 Mentha canadensis Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO22233 Allium schoenoprasum Species Amaryllidaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO21355 Elsholtzia ciliata Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO14579 Mentha spicata Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO1515 Lonicera japonica Species Caprifoliaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO8258 Camellia sinensis Species Theaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO4391 Hypericum perforatum Species Hypericaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO22233 Allium schoenoprasum Species Amaryllidaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO21355 Elsholtzia ciliata Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO1515 Lonicera japonica Species Caprifoliaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO18046 Mosla chinensis Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO18046 Mosla chinensis Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO13857 Mentha canadensis Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO23256 Mentha arvensis Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO21355 Elsholtzia ciliata Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO1515 Lonicera japonica Species Caprifoliaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO4391 Hypericum perforatum Species Hypericaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO26637 Mentha aquatica Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1515 Lonicera japonica Species Caprifoliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4391 Hypericum perforatum Species Hypericaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23256 Mentha arvensis Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22233 Allium schoenoprasum Species Amaryllidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18046 Mosla chinensis Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13857 Mentha canadensis Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21355 Elsholtzia ciliata Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8258 Camellia sinensis Species Theaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14579 Mentha spicata Species Lamiaceae 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
NPO14579 NPC100380 Other Leaf 1.3 0.1 2.5 mg/100g Database [DUKE]
NPO8258 NPC100380 Tea Or Coffee Leaf Essent. Oil 2 2 2 mg/100g Database [DUKE]
NPO14579 NPC100380 Other Shoot 4.25 0 8.5 mg/100g Database [DUKE]
NPO26637 NPC100380 Raw Shoot 0.055 0.01 0.1 mg/100g Database [DUKE]

☑ 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
NPT153 Individual Protein Androgen Receptor Homo sapiens Potency n.a. 68589.6 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 69.2 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 54941 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 68589.6 nM PubChem BioAssay data set
NPT1280 Organism Thrips tabaci Thrips tabaci Ratio = 1.2 n.a. PMID[548925]
NPT1281 Organism Thrips obscuratus Thrips obscuratus Ratio = 24.5 n.a. PMID[548925]
NPT1281 Organism Thrips obscuratus Thrips obscuratus Ratio = 42.1 n.a. PMID[548925]

☑ 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 NPC100380 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
0.913 High Similarity NPC145311
0.8444 Intermediate Similarity NPC301972
0.84 Intermediate Similarity NPC296311
0.8298 Intermediate Similarity NPC471752
0.8261 Intermediate Similarity NPC25771
0.814 Intermediate Similarity NPC155880
0.814 Intermediate Similarity NPC92863
0.8043 Intermediate Similarity NPC292463
0.8039 Intermediate Similarity NPC45283
0.8039 Intermediate Similarity NPC474141
0.7955 Intermediate Similarity NPC217923
0.7917 Intermediate Similarity NPC8610
0.7917 Intermediate Similarity NPC262558
0.7907 Intermediate Similarity NPC185839
0.7872 Intermediate Similarity NPC471753
0.7843 Intermediate Similarity NPC471751
0.78 Intermediate Similarity NPC32351
0.78 Intermediate Similarity NPC15325
0.7727 Intermediate Similarity NPC180840
0.7708 Intermediate Similarity NPC191337
0.7674 Intermediate Similarity NPC38497
0.766 Intermediate Similarity NPC216921
0.7647 Intermediate Similarity NPC477458
0.7593 Intermediate Similarity NPC20603
0.75 Intermediate Similarity NPC267514
0.75 Intermediate Similarity NPC145755
0.75 Intermediate Similarity NPC24833
0.75 Intermediate Similarity NPC477686
0.7455 Intermediate Similarity NPC281230
0.7455 Intermediate Similarity NPC192843
0.7451 Intermediate Similarity NPC176819
0.7451 Intermediate Similarity NPC163984
0.7451 Intermediate Similarity NPC474391
0.7451 Intermediate Similarity NPC58970
0.7407 Intermediate Similarity NPC275472
0.74 Intermediate Similarity NPC324812
0.7391 Intermediate Similarity NPC113082
0.7358 Intermediate Similarity NPC37644
0.7358 Intermediate Similarity NPC268564
0.7321 Intermediate Similarity NPC94991
0.7321 Intermediate Similarity NPC266295
0.7308 Intermediate Similarity NPC234829
0.7308 Intermediate Similarity NPC64866
0.7308 Intermediate Similarity NPC27438
0.7273 Intermediate Similarity NPC473733
0.7241 Intermediate Similarity NPC97322
0.7241 Intermediate Similarity NPC260573
0.7234 Intermediate Similarity NPC7754
0.7234 Intermediate Similarity NPC270170
0.7209 Intermediate Similarity NPC12889
0.72 Intermediate Similarity NPC4079
0.72 Intermediate Similarity NPC14917
0.72 Intermediate Similarity NPC236355
0.7193 Intermediate Similarity NPC143834
0.7193 Intermediate Similarity NPC259261
0.7143 Intermediate Similarity NPC193695
0.7143 Intermediate Similarity NPC115385
0.7119 Intermediate Similarity NPC167256
0.7115 Intermediate Similarity NPC118788
0.7115 Intermediate Similarity NPC228776
0.7111 Intermediate Similarity NPC220061
0.7083 Intermediate Similarity NPC287397
0.7083 Intermediate Similarity NPC298710
0.7083 Intermediate Similarity NPC67920
0.7069 Intermediate Similarity NPC25853
0.7059 Intermediate Similarity NPC91962
0.7045 Intermediate Similarity NPC269641
0.7021 Intermediate Similarity NPC111474
0.7018 Intermediate Similarity NPC311852
0.7018 Intermediate Similarity NPC30215
0.7 Intermediate Similarity NPC474202
0.7 Intermediate Similarity NPC239754
0.7 Intermediate Similarity NPC166788
0.7 Intermediate Similarity NPC474362
0.6977 Remote Similarity NPC266979
0.6957 Remote Similarity NPC130923
0.6949 Remote Similarity NPC213152
0.6909 Remote Similarity NPC63396
0.6909 Remote Similarity NPC202850
0.6909 Remote Similarity NPC189677
0.6897 Remote Similarity NPC472304
0.6897 Remote Similarity NPC96551
0.6897 Remote Similarity NPC276764
0.6897 Remote Similarity NPC285594
0.6885 Remote Similarity NPC133904
0.6875 Remote Similarity NPC33489
0.6863 Remote Similarity NPC110234
0.6863 Remote Similarity NPC163751
0.6863 Remote Similarity NPC44363
0.6842 Remote Similarity NPC49575
0.6842 Remote Similarity NPC55004
0.6842 Remote Similarity NPC267626
0.6842 Remote Similarity NPC230823
0.6833 Remote Similarity NPC322457
0.6833 Remote Similarity NPC165695
0.6833 Remote Similarity NPC477707
0.6833 Remote Similarity NPC288253
0.6833 Remote Similarity NPC32285
0.6792 Remote Similarity NPC20934
0.6792 Remote Similarity NPC225974
0.6792 Remote Similarity NPC288381
0.678 Remote Similarity NPC127582
0.6731 Remote Similarity NPC471958
0.6727 Remote Similarity NPC69898
0.6727 Remote Similarity NPC23117
0.6727 Remote Similarity NPC295777
0.6727 Remote Similarity NPC14002
0.6724 Remote Similarity NPC56905
0.6724 Remote Similarity NPC27610
0.6721 Remote Similarity NPC212210
0.6721 Remote Similarity NPC4638
0.6721 Remote Similarity NPC473902
0.6719 Remote Similarity NPC256846
0.6719 Remote Similarity NPC236208
0.6667 Remote Similarity NPC101147
0.6667 Remote Similarity NPC325977
0.6667 Remote Similarity NPC12319
0.6667 Remote Similarity NPC475795
0.6667 Remote Similarity NPC18205
0.6615 Remote Similarity NPC318766
0.6613 Remote Similarity NPC474329
0.6613 Remote Similarity NPC251118
0.6613 Remote Similarity NPC474304
0.661 Remote Similarity NPC106851
0.661 Remote Similarity NPC274927
0.6607 Remote Similarity NPC5626
0.6607 Remote Similarity NPC322461
0.66 Remote Similarity NPC106819
0.6562 Remote Similarity NPC476614
0.6557 Remote Similarity NPC477830
0.6557 Remote Similarity NPC57463
0.6557 Remote Similarity NPC151728
0.6538 Remote Similarity NPC276009
0.6538 Remote Similarity NPC195246
0.6538 Remote Similarity NPC22098
0.6508 Remote Similarity NPC16119
0.65 Remote Similarity NPC122521
0.65 Remote Similarity NPC174447
0.65 Remote Similarity NPC235242
0.65 Remote Similarity NPC251042
0.65 Remote Similarity NPC229252
0.65 Remote Similarity NPC143857
0.6491 Remote Similarity NPC188789
0.6491 Remote Similarity NPC478117
0.6481 Remote Similarity NPC224227
0.6481 Remote Similarity NPC59051
0.6481 Remote Similarity NPC116906
0.6458 Remote Similarity NPC33761
0.6452 Remote Similarity NPC150162
0.6452 Remote Similarity NPC34622
0.6452 Remote Similarity NPC474400
0.6452 Remote Similarity NPC285371
0.6452 Remote Similarity NPC6697
0.6452 Remote Similarity NPC475124
0.6441 Remote Similarity NPC170799
0.6441 Remote Similarity NPC308108
0.6441 Remote Similarity NPC60772
0.6429 Remote Similarity NPC217188
0.6406 Remote Similarity NPC475523
0.6406 Remote Similarity NPC474619
0.64 Remote Similarity NPC208936
0.6393 Remote Similarity NPC228574
0.6393 Remote Similarity NPC40082
0.6393 Remote Similarity NPC294304
0.6393 Remote Similarity NPC64985
0.6379 Remote Similarity NPC477201
0.6364 Remote Similarity NPC30433
0.6364 Remote Similarity NPC262968
0.6349 Remote Similarity NPC98897
0.6349 Remote Similarity NPC470688
0.6333 Remote Similarity NPC38455
0.6333 Remote Similarity NPC473494
0.6327 Remote Similarity NPC48930
0.6324 Remote Similarity NPC227396
0.6316 Remote Similarity NPC478120
0.6316 Remote Similarity NPC317796
0.6316 Remote Similarity NPC95581
0.6316 Remote Similarity NPC100809
0.6316 Remote Similarity NPC209431
0.6308 Remote Similarity NPC469679
0.6308 Remote Similarity NPC87141
0.6308 Remote Similarity NPC188292
0.6308 Remote Similarity NPC218477
0.6308 Remote Similarity NPC469688
0.6308 Remote Similarity NPC260474
0.6296 Remote Similarity NPC267110
0.629 Remote Similarity NPC210303
0.629 Remote Similarity NPC190049
0.629 Remote Similarity NPC197238
0.629 Remote Similarity NPC44343
0.629 Remote Similarity NPC202118
0.629 Remote Similarity NPC132243
0.629 Remote Similarity NPC179087
0.629 Remote Similarity NPC143168
0.629 Remote Similarity NPC53109
0.629 Remote Similarity NPC472306
0.6271 Remote Similarity NPC283502
0.6271 Remote Similarity NPC192427
0.6269 Remote Similarity NPC181204
0.6269 Remote Similarity NPC54123

  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 NPC100380 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
0.7556 Intermediate Similarity NPD5783 Phase 3
0.6508 Remote Similarity NPD6108 Clinical (unspecified phase)
0.6491 Remote Similarity NPD4627 Clinical (unspecified phase)
0.6441 Remote Similarity NPD287 Approved
0.6364 Remote Similarity NPD29 Approved
0.6364 Remote Similarity NPD28 Approved
0.6346 Remote Similarity NPD3174 Discontinued
0.629 Remote Similarity NPD2664 Clinical (unspecified phase)
0.625 Remote Similarity NPD7331 Phase 2
0.6212 Remote Similarity NPD4137 Phase 3
0.614 Remote Similarity NPD3172 Approved
0.6119 Remote Similarity NPD4747 Approved
0.6119 Remote Similarity NPD4691 Approved
0.6087 Remote Similarity NPD4687 Approved
0.6087 Remote Similarity NPD4058 Approved
0.6038 Remote Similarity NPD39 Approved
0.6038 Remote Similarity NPD4222 Approved
0.6034 Remote Similarity NPD4266 Approved
0.6034 Remote Similarity NPD3196 Approved
0.6034 Remote Similarity NPD3194 Approved
0.6034 Remote Similarity NPD539 Approved
0.6034 Remote Similarity NPD3195 Phase 2
0.6029 Remote Similarity NPD5276 Approved
0.6 Remote Similarity NPD3173 Approved
0.6 Remote Similarity NPD4220 Pre-registration
0.6 Remote Similarity NPD8779 Phase 3
0.5909 Remote Similarity NPD3709 Clinical (unspecified phase)
0.5857 Remote Similarity NPD5733 Approved
0.5821 Remote Similarity NPD3621 Clinical (unspecified phase)
0.5818 Remote Similarity NPD5343 Approved
0.566 Remote Similarity NPD5326 Phase 3
0.5658 Remote Similarity NPD5209 Approved
0.5625 Remote Similarity NPD4194 Approved
0.5625 Remote Similarity NPD4193 Approved
0.5625 Remote Similarity NPD4192 Approved
0.5625 Remote Similarity NPD4191 Approved
0.5606 Remote Similarity NPD7341 Phase 2

  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