Structure

Physi-Chem Properties

Molecular Weight:  244.11
Volume:  255.515
LogP:  2.867
LogD:  2.66
LogS:  -4.551
# Rotatable Bonds:  0
TPSA:  43.37
# H-Bond Aceptor:  3
# H-Bond Donor:  0
# Rings:  3
# Heavy Atoms:  3

MedChem Properties

QED Drug-Likeness Score:  0.486
Synthetic Accessibility Score:  4.311
Fsp3:  0.467
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Accepted
BMS Rule:  2
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.695
MDCK Permeability:  2.414659502392169e-05
Pgp-inhibitor:  0.979
Pgp-substrate:  0.0
Human Intestinal Absorption (HIA):  0.003
20% Bioavailability (F20%):  0.338
30% Bioavailability (F30%):  0.006

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.015
Plasma Protein Binding (PPB):  97.14944458007812%
Volume Distribution (VD):  1.328
Pgp-substrate:  1.8100742101669312%

ADMET: Metabolism

CYP1A2-inhibitor:  0.993
CYP1A2-substrate:  0.736
CYP2C19-inhibitor:  0.946
CYP2C19-substrate:  0.084
CYP2C9-inhibitor:  0.917
CYP2C9-substrate:  0.079
CYP2D6-inhibitor:  0.955
CYP2D6-substrate:  0.034
CYP3A4-inhibitor:  0.756
CYP3A4-substrate:  0.186

ADMET: Excretion

Clearance (CL):  4.277
Half-life (T1/2):  0.298

ADMET: Toxicity

hERG Blockers:  0.003
Human Hepatotoxicity (H-HT):  0.03
Drug-inuced Liver Injury (DILI):  0.49
AMES Toxicity:  0.038
Rat Oral Acute Toxicity:  0.685
Maximum Recommended Daily Dose:  0.839
Skin Sensitization:  0.836
Carcinogencity:  0.649
Eye Corrosion:  0.007
Eye Irritation:  0.162
Respiratory Toxicity:  0.946

Download Data

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Similar NPs/Drugs  

  Natural Product: NPC302426

Natural Product ID:  NPC302426
Common Name*:   Dehydroleucodin
IUPAC Name:   (3aS,9aS,9bS)-6,9-dimethyl-3-methylidene-4,5,9a,9b-tetrahydro-3aH-azuleno[4,5-b]furan-2,7-dione
Synonyms:   Dehydroleucodin; Dehydroleucodine
Standard InCHIKey:  SKNVIAFTENCNGB-BPNCWPANSA-N
Standard InCHI:  InChI=1S/C15H16O3/c1-7-4-5-10-9(3)15(17)18-14(10)13-8(2)6-11(16)12(7)13/h6,10,13-14H,3-5H2,1-2H3/t10-,13-,14-/m0/s1
SMILES:  CC1=C2C(=O)C=C(C)[C@@H]2[C@@H]2[C@@H](CC1)C(=C)C(=O)O2
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL441260
PubChem CID:   73440
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000002] Organoheterocyclic compounds
      • [CHEMONTID:0000050] Lactones
        • [CHEMONTID:0001245] Gamma butyrolactones

*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
NPO17790 Trigonostemon reidioides Species Euphorbiaceae Eukaryota roots Rat Buri Province, Thailand 1988-DEC PMID[14987064]
NPO17790 Trigonostemon reidioides Species Euphorbiaceae Eukaryota n.a. root n.a. PMID[16204992]
NPO9518 Gardenia jasminoides Species Rubiaceae Eukaryota Fruits n.a. n.a. PMID[16309325]
NPO9518 Gardenia jasminoides Species Rubiaceae Eukaryota n.a. Seoul, Korea 2000-Jun PMID[16643034]
NPO8524 Pithecellobium clypearia Species Fabaceae Eukaryota n.a. leaf n.a. PMID[16724853]
NPO8524 Pithecellobium clypearia Species Fabaceae Eukaryota leaves n.a. n.a. PMID[16724853]
NPO9518 Gardenia jasminoides Species Rubiaceae Eukaryota fruit n.a. n.a. PMID[18505286]
NPO9518 Gardenia jasminoides Species Rubiaceae Eukaryota fruit n.a. n.a. PMID[19650637]
NPO16660 Phomopsis archeri Species Valsaceae Eukaryota n.a. mycelium n.a. PMID[21341709]
NPO9518 Gardenia jasminoides Species Rubiaceae Eukaryota fruits n.a. n.a. PMID[23305920]
NPO28626 Isodon rubescens Species Lamiaceae Eukaryota n.a. n.a. n.a. PMID[25590529]
NPO13745 Gynoxys verrucosa Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[27057812]
NPO9518 Gardenia jasminoides Species Rubiaceae Eukaryota n.a. n.a. n.a. PMID[32141747]
NPO2733 Sarcomelicope argyrophylla Species Rutaceae Eukaryota n.a. n.a. n.a. Database[Article]
NPO10436 Aristolochia maxima Species Aristolochiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO13180 Jasminum officinale Species Oleaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO9518 Gardenia jasminoides Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO16620 Malus asiatica Species Rosaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO13856 Bergenia purpurascens Species Saxifragaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO17637 Pimpinella saxifraga Species Apiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO17706 Caragana tibetica Species Fabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO20293 Chrysanthemum lavandulifolium Species Asteraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO17706 Caragana tibetica Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO17244 Montrouziera sphaeroidea Species Clusiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO17637 Pimpinella saxifraga Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO13180 Jasminum officinale Species Oleaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO10436 Aristolochia maxima Species Aristolochiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO17790 Trigonostemon reidioides Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO28626 Isodon rubescens Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO9518 Gardenia jasminoides Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO20293 Chrysanthemum lavandulifolium Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO13856 Bergenia purpurascens Species Saxifragaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO20293 Chrysanthemum lavandulifolium Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO9518 Gardenia jasminoides Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO13180 Jasminum officinale Species Oleaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO28626 Isodon rubescens Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO9518 Gardenia jasminoides Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO12733 Pentapora fascialis Species Bitectiporidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10436 Aristolochia maxima Species Aristolochiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17100 Artemisia vachanica Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18709 Discaria crenata Species Rhamnaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14698 Phyllospongia madagascarensis Species Thorectidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18027 Oreosolen wattii Species Scrophulariaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17706 Caragana tibetica Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17355 Bischofia trifoliata Species Phyllanthaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13856 Bergenia purpurascens Species Saxifragaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26487 Tinospora smilacina Species Menispermaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16253 Rapanea myricoides Species Primulaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5634 Wallago attu Species Siluridae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11925 Mola mola Species Molidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13422 Amoora yunnanensis n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO9428 Annona rensoniana Species Annonaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28626 Isodon rubescens Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22469 Tropaeolum speciosum Species Tropaeolaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17870 Euphorbia ferganensis Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8524 Pithecellobium clypearia Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13180 Jasminum officinale Species Oleaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15079 Polygala myrtifolia Species Polygalaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16374 Crataegus sinaica Species Rosaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21802 Julocroton camporum n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO9523 Nephroma antarcticum Species Nephromataceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11559 Betula mandshurica Species Betulaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17029 Tridacna gigas Species Tridacnidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15814 Rhodiola krylovii Species Crassulaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14408 Chrysolina fastuosa Species Chrysomelidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2589 Solanum bahamense Species Solanaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1148 Phalium undulatum Species Cassidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17244 Montrouziera sphaeroidea Species Clusiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16620 Malus asiatica Species Rosaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11831 Achillea collina Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15667 Ligularia platyglossa Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20293 Chrysanthemum lavandulifolium Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9518 Gardenia jasminoides Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15964 Tropiometra afra Species Tropiometridae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2733 Sarcomelicope argyrophylla Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17790 Trigonostemon reidioides Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17637 Pimpinella saxifraga Species Apiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16660 Phomopsis archeri Species Valsaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17175 Lasiocephalus ovatus Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16510 Ganoderma australe Species Ganodermataceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6939 Vatica diospyroides Species Dipterocarpaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17739 Macrotyloma axillare Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12559 Mikania obtusata Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11420 Dolichospermum affine Species Aphanizomenonaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO13745 Gynoxys verrucosa Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18962 Actinobacillus pleuropneumoniae Species Pasteurellaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO11020 Streptomyces purpeofuscus Species Streptomycetaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO17945 Arachniodes dimorphophylla Species Dryopteridaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17327 Cotoneaster orbicularis Species Rosaceae 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
NPT441 Individual Protein Cytochrome P450 19A1 Homo sapiens IC50 = 15.0 nM PMID[529694]
NPT466 Cell Line U-937 Homo sapiens LD50 = 18.9 uM PMID[529695]
NPT1999 Cell Line TUR Homo sapiens LD50 = 12.2 uM PMID[529695]
NPT1970 Cell Line THP-1 Homo sapiens LD50 = 16.8 uM PMID[529695]
NPT1649 Cell Line MV4-11 Homo sapiens LD50 = 5.0 uM PMID[529695]
NPT6530 Cell Line MOLM-13 Homo sapiens LD50 = 12.6 uM PMID[529695]
NPT2100 Cell Line KG-1 LD50 = 18.7 uM PMID[529695]
NPT2085 Cell Line Kasumi 1 LD50 = 12.9 uM PMID[529695]
NPT116 Cell Line HL-60 Homo sapiens LD50 = 14.1 uM PMID[529695]
NPT83 Cell Line MCF7 Homo sapiens IC50 = 5000.0 nM PMID[529695]
NPT91 Cell Line KB Homo sapiens IC50 = 5300.0 nM PMID[529695]
NPT4720 Cell Line Leukemia cells Homo sapiens LD50 = 9.4 uM PMID[529695]
NPT29 Organism Rattus norvegicus Rattus norvegicus Cytoprotective effect = 0.25 n.a. PMID[529689]
NPT983 Protein Complex Nuclear factor NF-kappa-B complex Homo sapiens IC100 = 50.0 uM PMID[529690]
NPT983 Protein Complex Nuclear factor NF-kappa-B complex Homo sapiens pIC100 = -1.69 n.a. PMID[529690]
NPT721 Individual Protein Nuclear factor NF-kappa-B p65 subunit Homo sapiens IC100 = 50.0 uM PMID[529691]
NPT29 Organism Rattus norvegicus Rattus norvegicus FC = 7.0 n.a. PMID[529693]
NPT29 Organism Rattus norvegicus Rattus norvegicus UI = 0.3 n.a. PMID[529693]
NPT29 Organism Rattus norvegicus Rattus norvegicus UI = 2.4 n.a. PMID[529693]
NPT29 Organism Rattus norvegicus Rattus norvegicus UI = 1.2 n.a. PMID[529693]
NPT29 Organism Rattus norvegicus Rattus norvegicus UI = 3.3 n.a. PMID[529693]
NPT20987 CELL-LINE HeLa S3 Homo sapiens IC50 = 10000.0 nM PMID[529695]

☑ 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 NPC302426 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
0.9605 High Similarity NPC10276
0.9605 High Similarity NPC35089
0.9487 High Similarity NPC115786
0.9474 High Similarity NPC69271
0.9474 High Similarity NPC74673
0.9342 High Similarity NPC182550
0.9333 High Similarity NPC65603
0.9333 High Similarity NPC15975
0.9333 High Similarity NPC195785
0.9324 High Similarity NPC193351
0.9324 High Similarity NPC138408
0.9324 High Similarity NPC226669
0.925 High Similarity NPC107787
0.9221 High Similarity NPC276356
0.9211 High Similarity NPC299235
0.9125 High Similarity NPC78089
0.9114 High Similarity NPC39588
0.9114 High Similarity NPC215294
0.9091 High Similarity NPC472965
0.9091 High Similarity NPC264227
0.9091 High Similarity NPC63649
0.9079 High Similarity NPC470240
0.9079 High Similarity NPC476794
0.8916 High Similarity NPC268298
0.8889 High Similarity NPC161957
0.8889 High Similarity NPC21471
0.8889 High Similarity NPC33570
0.8861 High Similarity NPC25684
0.8861 High Similarity NPC301477
0.8861 High Similarity NPC281949
0.8861 High Similarity NPC255580
0.8861 High Similarity NPC39411
0.8846 High Similarity NPC470239
0.8846 High Similarity NPC470244
0.8816 High Similarity NPC155587
0.881 High Similarity NPC129419
0.8734 High Similarity NPC223904
0.8718 High Similarity NPC472960
0.8701 High Similarity NPC235906
0.8684 High Similarity NPC469643
0.8684 High Similarity NPC469641
0.859 High Similarity NPC41780
0.859 High Similarity NPC187568
0.8553 High Similarity NPC472956
0.8537 High Similarity NPC165287
0.8537 High Similarity NPC156485
0.8519 High Similarity NPC173609
0.8462 Intermediate Similarity NPC123360
0.8462 Intermediate Similarity NPC472967
0.8462 Intermediate Similarity NPC266159
0.8452 Intermediate Similarity NPC237540
0.8442 Intermediate Similarity NPC320537
0.8442 Intermediate Similarity NPC143979
0.8442 Intermediate Similarity NPC476355
0.8434 Intermediate Similarity NPC235792
0.8434 Intermediate Similarity NPC165162
0.8421 Intermediate Similarity NPC163003
0.8415 Intermediate Similarity NPC318468
0.84 Intermediate Similarity NPC296522
0.84 Intermediate Similarity NPC144511
0.8375 Intermediate Similarity NPC617
0.8354 Intermediate Similarity NPC208223
0.8353 Intermediate Similarity NPC91248
0.8333 Intermediate Similarity NPC67493
0.8312 Intermediate Similarity NPC58956
0.8312 Intermediate Similarity NPC269206
0.8312 Intermediate Similarity NPC295633
0.8289 Intermediate Similarity NPC472955
0.8276 Intermediate Similarity NPC74103
0.8276 Intermediate Similarity NPC123177
0.8276 Intermediate Similarity NPC150978
0.8276 Intermediate Similarity NPC70595
0.8272 Intermediate Similarity NPC290508
0.8272 Intermediate Similarity NPC293418
0.8272 Intermediate Similarity NPC6823
0.8272 Intermediate Similarity NPC73052
0.8256 Intermediate Similarity NPC4986
0.825 Intermediate Similarity NPC128276
0.8228 Intermediate Similarity NPC472959
0.8205 Intermediate Similarity NPC140287
0.8182 Intermediate Similarity NPC135776
0.8171 Intermediate Similarity NPC471325
0.8171 Intermediate Similarity NPC141810
0.8161 Intermediate Similarity NPC37607
0.8161 Intermediate Similarity NPC253144
0.8161 Intermediate Similarity NPC301969
0.8148 Intermediate Similarity NPC270126
0.8148 Intermediate Similarity NPC178277
0.814 Intermediate Similarity NPC224652
0.8125 Intermediate Similarity NPC122264
0.8125 Intermediate Similarity NPC53581
0.8125 Intermediate Similarity NPC57744
0.8125 Intermediate Similarity NPC103987
0.8118 Intermediate Similarity NPC64153
0.8118 Intermediate Similarity NPC284902
0.809 Intermediate Similarity NPC477131
0.809 Intermediate Similarity NPC167219
0.8072 Intermediate Similarity NPC89555
0.8072 Intermediate Similarity NPC178676
0.8068 Intermediate Similarity NPC133698
0.8068 Intermediate Similarity NPC300312
0.8068 Intermediate Similarity NPC131209
0.8068 Intermediate Similarity NPC261607
0.8068 Intermediate Similarity NPC284185
0.8068 Intermediate Similarity NPC111114
0.8026 Intermediate Similarity NPC470256
0.8025 Intermediate Similarity NPC93763
0.8025 Intermediate Similarity NPC108816
0.8023 Intermediate Similarity NPC475703
0.8 Intermediate Similarity NPC48803
0.8 Intermediate Similarity NPC215364
0.8 Intermediate Similarity NPC110405
0.8 Intermediate Similarity NPC275960
0.8 Intermediate Similarity NPC193645
0.8 Intermediate Similarity NPC90121
0.7976 Intermediate Similarity NPC54468
0.7976 Intermediate Similarity NPC272814
0.7976 Intermediate Similarity NPC475947
0.7975 Intermediate Similarity NPC472966
0.7955 Intermediate Similarity NPC62815
0.7952 Intermediate Similarity NPC42470
0.7949 Intermediate Similarity NPC129665
0.7931 Intermediate Similarity NPC215831
0.7931 Intermediate Similarity NPC190718
0.7927 Intermediate Similarity NPC469690
0.7922 Intermediate Similarity NPC5714
0.7907 Intermediate Similarity NPC38576
0.7907 Intermediate Similarity NPC279859
0.7907 Intermediate Similarity NPC305475
0.7907 Intermediate Similarity NPC475461
0.7907 Intermediate Similarity NPC150755
0.7901 Intermediate Similarity NPC97516
0.7901 Intermediate Similarity NPC476028
0.7901 Intermediate Similarity NPC141789
0.7901 Intermediate Similarity NPC171204
0.7901 Intermediate Similarity NPC320630
0.7901 Intermediate Similarity NPC7563
0.7901 Intermediate Similarity NPC116177
0.7889 Intermediate Similarity NPC470010
0.7889 Intermediate Similarity NPC262133
0.7889 Intermediate Similarity NPC470013
0.7889 Intermediate Similarity NPC323008
0.7889 Intermediate Similarity NPC198853
0.7882 Intermediate Similarity NPC475100
0.7882 Intermediate Similarity NPC114979
0.7882 Intermediate Similarity NPC96259
0.7882 Intermediate Similarity NPC141193
0.7882 Intermediate Similarity NPC191476
0.7875 Intermediate Similarity NPC244166
0.7857 Intermediate Similarity NPC246076
0.7841 Intermediate Similarity NPC32922
0.7841 Intermediate Similarity NPC295312
0.7841 Intermediate Similarity NPC73995
0.7838 Intermediate Similarity NPC474658
0.7831 Intermediate Similarity NPC281132
0.7826 Intermediate Similarity NPC169205
0.7816 Intermediate Similarity NPC72513
0.7816 Intermediate Similarity NPC160138
0.7805 Intermediate Similarity NPC196653
0.7805 Intermediate Similarity NPC471465
0.7805 Intermediate Similarity NPC267231
0.7802 Intermediate Similarity NPC67584
0.7802 Intermediate Similarity NPC304886
0.7802 Intermediate Similarity NPC52044
0.7791 Intermediate Similarity NPC255307
0.7791 Intermediate Similarity NPC177932
0.7778 Intermediate Similarity NPC473223
0.7765 Intermediate Similarity NPC193198
0.7765 Intermediate Similarity NPC22611
0.7765 Intermediate Similarity NPC474703
0.7765 Intermediate Similarity NPC245665
0.7765 Intermediate Similarity NPC250315
0.7753 Intermediate Similarity NPC71533
0.7753 Intermediate Similarity NPC77337
0.7753 Intermediate Similarity NPC152467
0.7753 Intermediate Similarity NPC106510
0.775 Intermediate Similarity NPC259599
0.775 Intermediate Similarity NPC15499
0.775 Intermediate Similarity NPC294434
0.775 Intermediate Similarity NPC117746
0.7742 Intermediate Similarity NPC141191
0.7742 Intermediate Similarity NPC54843
0.7738 Intermediate Similarity NPC470241
0.7738 Intermediate Similarity NPC325031
0.7727 Intermediate Similarity NPC469628
0.7727 Intermediate Similarity NPC469631
0.7727 Intermediate Similarity NPC475906
0.7727 Intermediate Similarity NPC469653
0.7727 Intermediate Similarity NPC226863
0.7727 Intermediate Similarity NPC471047
0.7717 Intermediate Similarity NPC213078
0.7717 Intermediate Similarity NPC185553
0.7711 Intermediate Similarity NPC98557
0.7711 Intermediate Similarity NPC89128
0.7711 Intermediate Similarity NPC167881
0.7711 Intermediate Similarity NPC469620
0.7708 Intermediate Similarity NPC100487
0.7701 Intermediate Similarity NPC70555
0.7701 Intermediate Similarity NPC236692
0.7701 Intermediate Similarity NPC70422

  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 NPC302426 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
0.8256 Intermediate Similarity NPD1695 Approved
0.8 Intermediate Similarity NPD1698 Clinical (unspecified phase)
0.7791 Intermediate Similarity NPD1694 Approved
0.7586 Intermediate Similarity NPD1733 Clinical (unspecified phase)
0.7241 Intermediate Similarity NPD4752 Clinical (unspecified phase)
0.72 Intermediate Similarity NPD7899 Clinical (unspecified phase)
0.7174 Intermediate Similarity NPD5785 Approved
0.7045 Intermediate Similarity NPD5209 Approved
0.7 Intermediate Similarity NPD5363 Approved
0.6966 Remote Similarity NPD7154 Phase 3
0.6966 Remote Similarity NPD5362 Discontinued
0.6962 Remote Similarity NPD2685 Clinical (unspecified phase)
0.6957 Remote Similarity NPD6903 Approved
0.6923 Remote Similarity NPD5330 Approved
0.6923 Remote Similarity NPD7521 Approved
0.6923 Remote Similarity NPD6684 Approved
0.6923 Remote Similarity NPD6409 Approved
0.6923 Remote Similarity NPD7146 Approved
0.6923 Remote Similarity NPD7334 Approved
0.6827 Remote Similarity NPD6371 Approved
0.6774 Remote Similarity NPD7513 Clinical (unspecified phase)
0.6742 Remote Similarity NPD5369 Approved
0.6667 Remote Similarity NPD4269 Approved
0.6667 Remote Similarity NPD4270 Approved
0.6632 Remote Similarity NPD46 Approved
0.6632 Remote Similarity NPD6698 Approved
0.6632 Remote Similarity NPD5207 Approved
0.663 Remote Similarity NPD6082 Clinical (unspecified phase)
0.6628 Remote Similarity NPD8039 Approved
0.6598 Remote Similarity NPD5282 Discontinued
0.6596 Remote Similarity NPD6672 Approved
0.6596 Remote Similarity NPD5737 Approved
0.6562 Remote Similarity NPD5693 Phase 1
0.6559 Remote Similarity NPD5786 Approved
0.6531 Remote Similarity NPD6356 Clinical (unspecified phase)
0.65 Remote Similarity NPD4225 Approved
0.6495 Remote Similarity NPD6399 Phase 3
0.6484 Remote Similarity NPD6435 Approved
0.6444 Remote Similarity NPD4252 Approved
0.6442 Remote Similarity NPD6008 Approved
0.6429 Remote Similarity NPD6001 Approved
0.6404 Remote Similarity NPD5784 Clinical (unspecified phase)
0.6289 Remote Similarity NPD7838 Discovery
0.6264 Remote Similarity NPD5368 Approved
0.6264 Remote Similarity NPD5790 Clinical (unspecified phase)
0.6263 Remote Similarity NPD7901 Clinical (unspecified phase)
0.6263 Remote Similarity NPD7900 Approved
0.625 Remote Similarity NPD5208 Approved
0.6239 Remote Similarity NPD6053 Discontinued
0.6237 Remote Similarity NPD5331 Approved
0.6237 Remote Similarity NPD5332 Approved
0.6211 Remote Similarity NPD3618 Phase 1
0.6211 Remote Similarity NPD4249 Approved
0.62 Remote Similarity NPD5695 Phase 3
0.6196 Remote Similarity NPD4790 Discontinued
0.6186 Remote Similarity NPD6904 Approved
0.6186 Remote Similarity NPD6673 Approved
0.6186 Remote Similarity NPD6080 Approved
0.6176 Remote Similarity NPD5696 Approved
0.6176 Remote Similarity NPD7638 Approved
0.617 Remote Similarity NPD3133 Approved
0.617 Remote Similarity NPD3666 Approved
0.617 Remote Similarity NPD3665 Phase 1
0.6161 Remote Similarity NPD7115 Discovery
0.6146 Remote Similarity NPD4251 Approved
0.6146 Remote Similarity NPD4250 Approved
0.6146 Remote Similarity NPD3573 Approved
0.6129 Remote Similarity NPD3667 Approved
0.6122 Remote Similarity NPD5692 Phase 3
0.6117 Remote Similarity NPD7639 Approved
0.6117 Remote Similarity NPD7640 Approved
0.6111 Remote Similarity NPD4756 Discovery
0.61 Remote Similarity NPD7748 Approved
0.6087 Remote Similarity NPD4819 Approved
0.6087 Remote Similarity NPD4820 Approved
0.6087 Remote Similarity NPD4822 Approved
0.6087 Remote Similarity NPD4821 Approved
0.6078 Remote Similarity NPD6084 Phase 2
0.6078 Remote Similarity NPD6083 Phase 2
0.6078 Remote Similarity NPD7902 Approved
0.6071 Remote Similarity NPD7331 Phase 2
0.6071 Remote Similarity NPD6108 Clinical (unspecified phase)
0.6061 Remote Similarity NPD5694 Approved
0.6061 Remote Similarity NPD6050 Approved
0.6044 Remote Similarity NPD4268 Approved
0.6044 Remote Similarity NPD4271 Approved
0.6042 Remote Similarity NPD6098 Approved
0.6042 Remote Similarity NPD5279 Phase 3
0.602 Remote Similarity NPD6101 Approved
0.602 Remote Similarity NPD5764 Clinical (unspecified phase)
0.6019 Remote Similarity NPD6686 Approved
0.6019 Remote Similarity NPD8029 Clinical (unspecified phase)
0.6 Remote Similarity NPD3668 Phase 3
0.6 Remote Similarity NPD5779 Approved
0.6 Remote Similarity NPD5778 Approved
0.6 Remote Similarity NPD2181 Clinical (unspecified phase)
0.6 Remote Similarity NPD4786 Approved
0.5952 Remote Similarity NPD7341 Phase 2
0.5943 Remote Similarity NPD6052 Approved
0.5926 Remote Similarity NPD5697 Approved
0.5914 Remote Similarity NPD4695 Discontinued
0.59 Remote Similarity NPD7515 Phase 2
0.59 Remote Similarity NPD5281 Approved
0.59 Remote Similarity NPD7983 Approved
0.59 Remote Similarity NPD6411 Approved
0.59 Remote Similarity NPD5284 Approved
0.59 Remote Similarity NPD6079 Approved
0.5876 Remote Similarity NPD6422 Discontinued
0.5872 Remote Similarity NPD7320 Approved
0.5872 Remote Similarity NPD6899 Approved
0.5872 Remote Similarity NPD6011 Approved
0.5872 Remote Similarity NPD6881 Approved
0.5859 Remote Similarity NPD5328 Approved
0.5859 Remote Similarity NPD5370 Suspended
0.5859 Remote Similarity NPD6051 Approved
0.5856 Remote Similarity NPD6649 Approved
0.5856 Remote Similarity NPD8413 Clinical (unspecified phase)
0.5856 Remote Similarity NPD6650 Approved
0.5833 Remote Similarity NPD6675 Approved
0.5833 Remote Similarity NPD5739 Approved
0.5833 Remote Similarity NPD7128 Approved
0.5833 Remote Similarity NPD6402 Approved
0.5833 Remote Similarity NPD6400 Clinical (unspecified phase)
0.5825 Remote Similarity NPD5349 Clinical (unspecified phase)
0.5818 Remote Similarity NPD6013 Approved
0.5818 Remote Similarity NPD6373 Approved
0.5818 Remote Similarity NPD6012 Approved
0.5818 Remote Similarity NPD6014 Approved
0.5818 Remote Similarity NPD6372 Approved
0.5795 Remote Similarity NPD4691 Approved
0.5789 Remote Similarity NPD4221 Approved
0.5789 Remote Similarity NPD4223 Phase 3
0.578 Remote Similarity NPD5701 Approved
0.5766 Remote Similarity NPD7102 Approved
0.5766 Remote Similarity NPD6883 Approved
0.5766 Remote Similarity NPD2067 Discontinued
0.5766 Remote Similarity NPD7290 Approved
0.5743 Remote Similarity NPD4810 Clinical (unspecified phase)
0.5728 Remote Similarity NPD5654 Approved
0.5728 Remote Similarity NPD5210 Approved
0.5728 Remote Similarity NPD4629 Approved
0.5714 Remote Similarity NPD6927 Phase 3
0.5714 Remote Similarity NPD29 Approved
0.5714 Remote Similarity NPD5690 Phase 2
0.5714 Remote Similarity NPD6869 Approved
0.5714 Remote Similarity NPD6847 Approved
0.5714 Remote Similarity NPD3574 Clinical (unspecified phase)
0.5714 Remote Similarity NPD8130 Phase 1
0.5714 Remote Similarity NPD6617 Approved
0.5714 Remote Similarity NPD28 Approved
0.5714 Remote Similarity NPD2664 Clinical (unspecified phase)
0.5714 Remote Similarity NPD4519 Discontinued
0.5714 Remote Similarity NPD4623 Approved
0.57 Remote Similarity NPD4753 Phase 2
0.5696 Remote Similarity NPD9298 Approved
0.5686 Remote Similarity NPD4202 Approved
0.5684 Remote Similarity NPD857 Phase 3
0.5682 Remote Similarity NPD4137 Phase 3
0.5678 Remote Similarity NPD6291 Clinical (unspecified phase)
0.5673 Remote Similarity NPD4697 Phase 3
0.5673 Remote Similarity NPD7839 Suspended
0.5673 Remote Similarity NPD5221 Approved
0.5673 Remote Similarity NPD5220 Clinical (unspecified phase)
0.5673 Remote Similarity NPD5222 Approved
0.567 Remote Similarity NPD4197 Approved
0.5664 Remote Similarity NPD8297 Approved
0.5664 Remote Similarity NPD6882 Approved
0.566 Remote Similarity NPD6648 Approved
0.5648 Remote Similarity NPD6647 Phase 2
0.5647 Remote Similarity NPD3197 Phase 1
0.5647 Remote Similarity NPD5325 Clinical (unspecified phase)
0.5636 Remote Similarity NPD6614 Approved
0.5636 Remote Similarity NPD5954 Clinical (unspecified phase)
0.5625 Remote Similarity NPD4800 Clinical (unspecified phase)
0.5619 Remote Similarity NPD5173 Approved
0.5619 Remote Similarity NPD5959 Approved
0.5618 Remote Similarity NPD4747 Approved
0.5612 Remote Similarity NPD5329 Approved
0.5612 Remote Similarity NPD1696 Phase 3
0.5607 Remote Similarity NPD5344 Discontinued
0.5604 Remote Similarity NPD4058 Approved
0.56 Remote Similarity NPD4518 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