Structure

Physi-Chem Properties

Molecular Weight:  356.16
Volume:  371.599
LogP:  3.174
LogD:  2.78
LogS:  -4.642
# Rotatable Bonds:  6
TPSA:  53.99
# H-Bond Aceptor:  5
# H-Bond Donor:  0
# Rings:  3
# Heavy Atoms:  5

MedChem Properties

QED Drug-Likeness Score:  0.727
Synthetic Accessibility Score:  4.064
Fsp3:  0.381
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Rejected
GSK Rule:  Accepted
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.584
MDCK Permeability:  1.7193411622429267e-05
Pgp-inhibitor:  0.997
Pgp-substrate:  0.0
Human Intestinal Absorption (HIA):  0.01
20% Bioavailability (F20%):  0.05
30% Bioavailability (F30%):  0.928

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.299
Plasma Protein Binding (PPB):  80.37195587158203%
Volume Distribution (VD):  1.236
Pgp-substrate:  9.32431697845459%

ADMET: Metabolism

CYP1A2-inhibitor:  0.162
CYP1A2-substrate:  0.962
CYP2C19-inhibitor:  0.678
CYP2C19-substrate:  0.852
CYP2C9-inhibitor:  0.588
CYP2C9-substrate:  0.14
CYP2D6-inhibitor:  0.486
CYP2D6-substrate:  0.342
CYP3A4-inhibitor:  0.884
CYP3A4-substrate:  0.917

ADMET: Excretion

Clearance (CL):  11.753
Half-life (T1/2):  0.4

ADMET: Toxicity

hERG Blockers:  0.107
Human Hepatotoxicity (H-HT):  0.609
Drug-inuced Liver Injury (DILI):  0.093
AMES Toxicity:  0.025
Rat Oral Acute Toxicity:  0.896
Maximum Recommended Daily Dose:  0.771
Skin Sensitization:  0.777
Carcinogencity:  0.9
Eye Corrosion:  0.004
Eye Irritation:  0.018
Respiratory Toxicity:  0.973

Download Data

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

  Natural Product: NPC280399

Natural Product ID:  NPC280399
Common Name*:   Kadsurenone
IUPAC Name:   (2S,3R,3aS)-2-(3,4-dimethoxyphenyl)-3a-methoxy-3-methyl-5-prop-2-enyl-2,3-dihydro-1-benzofuran-6-one
Synonyms:   (+)-Kadsurenone; Kadsurenone
Standard InCHIKey:  VDYACOATPFOZIO-UBWHGVKJSA-N
Standard InCHI:  InChI=1S/C21H24O5/c1-6-7-15-12-21(25-5)13(2)20(26-19(21)11-16(15)22)14-8-9-17(23-3)18(10-14)24-4/h6,8-13,20H,1,7H2,2-5H3/t13-,20+,21+/m1/s1
SMILES:  C=CCC1=C[C@@]2([C@H](C)[C@@H](c3ccc(c(c3)OC)OC)OC2=CC1=O)OC
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL296958
PubChem CID:   122159
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000261] Phenylpropanoids and polyketides
      • [CHEMONTID:0003405] 2-arylbenzofuran flavonoids

*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
NPO4865 Piper kadsura Species Piperaceae Eukaryota n.a. n.a. n.a. PMID[11040054]
NPO4865 Piper kadsura Species Piperaceae Eukaryota n.a. n.a. n.a. PMID[16724856]
NPO4682 Lindera aggregata Species Lauraceae Eukaryota n.a. leaf n.a. PMID[17999353]
NPO19526 Pleurothyrium cinereum Species Lauraceae Eukaryota leaves n.a. n.a. PMID[19548690]
NPO4682 Lindera aggregata Species Lauraceae Eukaryota Roots; Tubers n.a. n.a. PMID[19639966]
NPO27964 Nectandra amazonum Species Lauraceae Eukaryota leaves n.a. n.a. PMID[19880317]
NPO19526 Pleurothyrium cinereum Species Lauraceae Eukaryota leaves n.a. n.a. PMID[19880317]
NPO26326 Ocotea macrophylla Species Lauraceae Eukaryota leaves n.a. n.a. PMID[19880317]
NPO4865 Piper kadsura Species Piperaceae Eukaryota n.a. n.a. n.a. PMID[19900811]
NPO9925 Rhododendron latoucheae Species Ericaceae Eukaryota Twigs; Leaves n.a. n.a. PMID[30106288]
NPO15473 Ocotea heterochroma Species Lauraceae Eukaryota leaves n.a. n.a. PMID[30188730]
NPO4865 Piper kadsura Species Piperaceae Eukaryota n.a. aerial part n.a. PMID[8237383]
NPO4865 Piper kadsura Species Piperaceae Eukaryota n.a. n.a. n.a. PMID[8237383]
NPO4865 Piper kadsura Species Piperaceae Eukaryota n.a. n.a. n.a. PMID[8368081]
NPO9480 Huperzia miyoshiana Species Lycopodiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO4865 Piper kadsura Species Piperaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO9480 Huperzia miyoshiana Species Lycopodiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO4865 Piper kadsura Species Piperaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO4682 Lindera aggregata Species Lauraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO4865 Piper kadsura Species Piperaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO4682 Lindera aggregata Species Lauraceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO4865 Piper kadsura Species Piperaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO7522 Streptomyces amakusaensis Species Streptomycetaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO313 Castilleja sulphurea Species Orobanchaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9571 Pseudobrickellia brasiliensis Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9301 Dioscorea sativa Species Dioscoreaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9925 Rhododendron latoucheae Species Ericaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26326 Ocotea macrophylla Species Lauraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19174 Anoplophora chinensis Species Cerambycidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9480 Huperzia miyoshiana Species Lycopodiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1155 Forsythia japonica Species Oleaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4682 Lindera aggregata Species Lauraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6475 Gymnosporia trigyna Species Celastraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15473 Ocotea heterochroma Species Lauraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27964 Nectandra amazonum Species Lauraceae 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
NPT1372 Individual Protein Platelet activating factor receptor Cavia porcellus IC50 = 3300.0 nM PMID[476753]
NPT1372 Individual Protein Platelet activating factor receptor Cavia porcellus IC50 = 150.0 nM PMID[476754]
NPT1372 Individual Protein Platelet activating factor receptor Cavia porcellus Inhibition = 68.0 % PMID[476756]
NPT1372 Individual Protein Platelet activating factor receptor Cavia porcellus Inhibition = 84.0 % PMID[476756]
NPT1372 Individual Protein Platelet activating factor receptor Cavia porcellus Inhibition = 95.0 % PMID[476756]
NPT1372 Individual Protein Platelet activating factor receptor Cavia porcellus IC50 = 120.0 nM PMID[476756]
NPT1372 Individual Protein Platelet activating factor receptor Cavia porcellus Inhibition = 57.0 % PMID[476757]
NPT1372 Individual Protein Platelet activating factor receptor Cavia porcellus Inhibition = 77.0 % PMID[476757]
NPT1372 Individual Protein Platelet activating factor receptor Cavia porcellus Inhibition = 94.0 % PMID[476757]
NPT1372 Individual Protein Platelet activating factor receptor Cavia porcellus IC50 = 240.0 nM PMID[476757]
NPT1372 Individual Protein Platelet activating factor receptor Cavia porcellus IC50 = 200.0 nM PMID[476757]
NPT1372 Individual Protein Platelet activating factor receptor Cavia porcellus IC50 = 100.0 nM PMID[476757]
NPT324 Individual Protein Cyclooxygenase-1 Ovis aries IC50 = 25600.0 nM PMID[476759]
NPT325 Individual Protein Cyclooxygenase-2 Ovis aries IC50 = 246000.0 nM PMID[476759]
NPT419 Organism Oryctolagus cuniculus Oryctolagus cuniculus IC50 = 3300.0 nM PMID[476752]
NPT419 Organism Oryctolagus cuniculus Oryctolagus cuniculus IC50 = 3300.0 nM PMID[476755]
NPT419 Organism Oryctolagus cuniculus Oryctolagus cuniculus Ki = 58.0 nM PMID[476756]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. IC50 = 120.0 nM PMID[476758]
NPT2 Others Unspecified IC50 = 104.0 nM PMID[476759]
NPT2 Others Unspecified Ratio IC50 = 12.6 n.a. PMID[476759]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. IC50 = 153.0 nM PMID[476759]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. IC50 = 5610.0 nM PMID[476759]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. IC50 = 38100.0 nM PMID[476759]
NPT27 Others Unspecified Inhibition = 21.3 % PMID[476760]
NPT2 Others Unspecified IC50 = 150.0 nM PMID[476761]

☑ 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 NPC280399 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
1.0 High Similarity NPC233961
1.0 High Similarity NPC339621
0.9685 High Similarity NPC145769
0.9462 High Similarity NPC166184
0.9248 High Similarity NPC51681
0.9044 High Similarity NPC15743
0.8984 High Similarity NPC64948
0.896 High Similarity NPC126935
0.896 High Similarity NPC216929
0.896 High Similarity NPC312713
0.896 High Similarity NPC65933
0.896 High Similarity NPC172676
0.896 High Similarity NPC57268
0.8939 High Similarity NPC37065
0.8898 High Similarity NPC34902
0.8898 High Similarity NPC121783
0.8898 High Similarity NPC18449
0.8889 High Similarity NPC278076
0.8832 High Similarity NPC474966
0.878 High Similarity NPC268317
0.876 High Similarity NPC112571
0.876 High Similarity NPC206882
0.876 High Similarity NPC285725
0.876 High Similarity NPC50683
0.8759 High Similarity NPC46180
0.8759 High Similarity NPC476840
0.8759 High Similarity NPC476842
0.8643 High Similarity NPC30890
0.8633 High Similarity NPC50696
0.8626 High Similarity NPC470084
0.8626 High Similarity NPC222127
0.8626 High Similarity NPC82862
0.8615 High Similarity NPC88297
0.8615 High Similarity NPC9891
0.8615 High Similarity NPC186845
0.8603 High Similarity NPC281780
0.8594 High Similarity NPC256167
0.8582 High Similarity NPC25496
0.8571 High Similarity NPC277804
0.855 High Similarity NPC8050
0.855 High Similarity NPC473093
0.855 High Similarity NPC98745
0.855 High Similarity NPC473092
0.8529 High Similarity NPC471988
0.8519 High Similarity NPC67247
0.8507 High Similarity NPC207400
0.8507 High Similarity NPC181049
0.8496 Intermediate Similarity NPC153739
0.8496 Intermediate Similarity NPC64201
0.8496 Intermediate Similarity NPC241522
0.8496 Intermediate Similarity NPC242807
0.8496 Intermediate Similarity NPC92164
0.8496 Intermediate Similarity NPC145305
0.8496 Intermediate Similarity NPC42300
0.8496 Intermediate Similarity NPC77040
0.8496 Intermediate Similarity NPC174495
0.8496 Intermediate Similarity NPC187998
0.8496 Intermediate Similarity NPC257582
0.8489 Intermediate Similarity NPC67467
0.8485 Intermediate Similarity NPC282703
0.8485 Intermediate Similarity NPC184733
0.8485 Intermediate Similarity NPC21867
0.8485 Intermediate Similarity NPC57119
0.8485 Intermediate Similarity NPC328682
0.8485 Intermediate Similarity NPC54321
0.8485 Intermediate Similarity NPC11258
0.8485 Intermediate Similarity NPC128208
0.8485 Intermediate Similarity NPC45774
0.8485 Intermediate Similarity NPC281864
0.8485 Intermediate Similarity NPC129570
0.8485 Intermediate Similarity NPC165128
0.8485 Intermediate Similarity NPC158471
0.8485 Intermediate Similarity NPC226862
0.8478 Intermediate Similarity NPC322021
0.8456 Intermediate Similarity NPC211386
0.8456 Intermediate Similarity NPC174191
0.844 Intermediate Similarity NPC476843
0.844 Intermediate Similarity NPC476841
0.8433 Intermediate Similarity NPC227160
0.8433 Intermediate Similarity NPC228346
0.8433 Intermediate Similarity NPC40432
0.8433 Intermediate Similarity NPC161557
0.8433 Intermediate Similarity NPC82111
0.8433 Intermediate Similarity NPC158079
0.8433 Intermediate Similarity NPC7171
0.8433 Intermediate Similarity NPC27843
0.8433 Intermediate Similarity NPC115207
0.8421 Intermediate Similarity NPC475875
0.8413 Intermediate Similarity NPC185738
0.8409 Intermediate Similarity NPC223807
0.8403 Intermediate Similarity NPC475170
0.8397 Intermediate Similarity NPC85830
0.8392 Intermediate Similarity NPC236166
0.8385 Intermediate Similarity NPC279379
0.837 Intermediate Similarity NPC2190
0.837 Intermediate Similarity NPC18842
0.837 Intermediate Similarity NPC4940
0.837 Intermediate Similarity NPC7744
0.837 Intermediate Similarity NPC230219
0.8369 Intermediate Similarity NPC264706
0.8369 Intermediate Similarity NPC474444
0.8369 Intermediate Similarity NPC284881
0.8369 Intermediate Similarity NPC93433
0.8358 Intermediate Similarity NPC237169
0.8358 Intermediate Similarity NPC233224
0.8358 Intermediate Similarity NPC470624
0.8358 Intermediate Similarity NPC271208
0.8345 Intermediate Similarity NPC62354
0.8345 Intermediate Similarity NPC147379
0.8333 Intermediate Similarity NPC9341
0.8333 Intermediate Similarity NPC81067
0.8322 Intermediate Similarity NPC153620
0.8322 Intermediate Similarity NPC24257
0.8322 Intermediate Similarity NPC476359
0.8322 Intermediate Similarity NPC476338
0.8322 Intermediate Similarity NPC30720
0.8321 Intermediate Similarity NPC44245
0.8321 Intermediate Similarity NPC72796
0.831 Intermediate Similarity NPC163898
0.8309 Intermediate Similarity NPC158331
0.8309 Intermediate Similarity NPC266848
0.8309 Intermediate Similarity NPC26394
0.8309 Intermediate Similarity NPC1474
0.8309 Intermediate Similarity NPC136750
0.8309 Intermediate Similarity NPC327410
0.8308 Intermediate Similarity NPC288238
0.8308 Intermediate Similarity NPC286573
0.8296 Intermediate Similarity NPC469480
0.8295 Intermediate Similarity NPC267064
0.8288 Intermediate Similarity NPC151425
0.8286 Intermediate Similarity NPC100675
0.8276 Intermediate Similarity NPC12854
0.8273 Intermediate Similarity NPC178290
0.8271 Intermediate Similarity NPC165045
0.8271 Intermediate Similarity NPC5428
0.8271 Intermediate Similarity NPC118533
0.8261 Intermediate Similarity NPC209229
0.8261 Intermediate Similarity NPC143895
0.8254 Intermediate Similarity NPC47194
0.8252 Intermediate Similarity NPC476362
0.8248 Intermediate Similarity NPC474478
0.8248 Intermediate Similarity NPC135127
0.8248 Intermediate Similarity NPC237594
0.8248 Intermediate Similarity NPC16485
0.8248 Intermediate Similarity NPC476387
0.8248 Intermediate Similarity NPC249791
0.8248 Intermediate Similarity NPC287745
0.8248 Intermediate Similarity NPC119060
0.8244 Intermediate Similarity NPC108545
0.8244 Intermediate Similarity NPC21238
0.824 Intermediate Similarity NPC165106
0.8235 Intermediate Similarity NPC33611
0.8235 Intermediate Similarity NPC100223
0.8235 Intermediate Similarity NPC16830
0.8235 Intermediate Similarity NPC65183
0.8235 Intermediate Similarity NPC204215
0.8235 Intermediate Similarity NPC72046
0.8235 Intermediate Similarity NPC475856
0.8235 Intermediate Similarity NPC129687
0.8235 Intermediate Similarity NPC239302
0.8235 Intermediate Similarity NPC171928
0.8235 Intermediate Similarity NPC158526
0.8235 Intermediate Similarity NPC175067
0.8235 Intermediate Similarity NPC261812
0.8231 Intermediate Similarity NPC477886
0.8231 Intermediate Similarity NPC327225
0.8231 Intermediate Similarity NPC114845
0.8231 Intermediate Similarity NPC308555
0.8227 Intermediate Similarity NPC253722
0.8227 Intermediate Similarity NPC31751
0.8227 Intermediate Similarity NPC253481
0.8222 Intermediate Similarity NPC142985
0.8209 Intermediate Similarity NPC210674
0.8203 Intermediate Similarity NPC277460
0.8195 Intermediate Similarity NPC127604
0.8188 Intermediate Similarity NPC99572
0.8188 Intermediate Similarity NPC126409
0.8188 Intermediate Similarity NPC474139
0.8188 Intermediate Similarity NPC189474
0.8182 Intermediate Similarity NPC232883
0.8182 Intermediate Similarity NPC223185
0.8176 Intermediate Similarity NPC25127
0.8168 Intermediate Similarity NPC261661
0.8163 Intermediate Similarity NPC267091
0.8163 Intermediate Similarity NPC476434
0.8163 Intermediate Similarity NPC476335
0.8162 Intermediate Similarity NPC192255
0.8154 Intermediate Similarity NPC471877
0.8151 Intermediate Similarity NPC316989
0.8148 Intermediate Similarity NPC476748
0.8143 Intermediate Similarity NPC470962
0.814 Intermediate Similarity NPC135961
0.814 Intermediate Similarity NPC475961
0.814 Intermediate Similarity NPC254625
0.8138 Intermediate Similarity NPC252281
0.8138 Intermediate Similarity NPC477375
0.8138 Intermediate Similarity NPC102934
0.8138 Intermediate Similarity NPC198129
0.8138 Intermediate Similarity NPC473408
0.8138 Intermediate Similarity NPC252402

  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 NPC280399 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
0.8413 Intermediate Similarity NPD5536 Phase 2
0.824 Intermediate Similarity NPD5283 Phase 1
0.8231 Intermediate Similarity NPD3705 Approved
0.797 Intermediate Similarity NPD4379 Clinical (unspecified phase)
0.7908 Intermediate Similarity NPD5494 Approved
0.7883 Intermediate Similarity NPD3027 Phase 3
0.777 Intermediate Similarity NPD6980 Clinical (unspecified phase)
0.7687 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.7674 Intermediate Similarity NPD1241 Discontinued
0.7619 Intermediate Similarity NPD1358 Approved
0.7603 Intermediate Similarity NPD4110 Phase 3
0.7603 Intermediate Similarity NPD4109 Clinical (unspecified phase)
0.7584 Intermediate Similarity NPD7314 Clinical (unspecified phase)
0.754 Intermediate Similarity NPD3134 Approved
0.7516 Intermediate Similarity NPD37 Approved
0.7516 Intermediate Similarity NPD1934 Approved
0.75 Intermediate Similarity NPD7028 Phase 2
0.75 Intermediate Similarity NPD2981 Phase 2
0.7484 Intermediate Similarity NPD4965 Approved
0.7484 Intermediate Similarity NPD4966 Approved
0.7484 Intermediate Similarity NPD4967 Phase 2
0.7484 Intermediate Similarity NPD3882 Suspended
0.7466 Intermediate Similarity NPD2424 Discontinued
0.7463 Intermediate Similarity NPD5691 Approved
0.7445 Intermediate Similarity NPD2983 Phase 2
0.7445 Intermediate Similarity NPD2982 Phase 2
0.7405 Intermediate Similarity NPD8127 Discontinued
0.7397 Intermediate Similarity NPD1375 Discontinued
0.7391 Intermediate Similarity NPD1876 Approved
0.7389 Intermediate Similarity NPD6234 Discontinued
0.7385 Intermediate Similarity NPD228 Approved
0.7368 Intermediate Similarity NPD4210 Discontinued
0.7365 Intermediate Similarity NPD4628 Phase 3
0.7357 Intermediate Similarity NPD2861 Phase 2
0.7357 Intermediate Similarity NPD3018 Phase 2
0.7355 Intermediate Similarity NPD2393 Clinical (unspecified phase)
0.7349 Intermediate Similarity NPD8055 Clinical (unspecified phase)
0.7343 Intermediate Similarity NPD1613 Approved
0.7343 Intermediate Similarity NPD1612 Clinical (unspecified phase)
0.7338 Intermediate Similarity NPD6385 Approved
0.7338 Intermediate Similarity NPD6386 Approved
0.7333 Intermediate Similarity NPD4357 Discontinued
0.7333 Intermediate Similarity NPD1357 Approved
0.7333 Intermediate Similarity NPD5585 Approved
0.7333 Intermediate Similarity NPD1651 Approved
0.7329 Intermediate Similarity NPD2438 Suspended
0.7329 Intermediate Similarity NPD2796 Approved
0.7315 Intermediate Similarity NPD5307 Clinical (unspecified phase)
0.7312 Intermediate Similarity NPD3926 Phase 2
0.7308 Intermediate Similarity NPD3817 Phase 2
0.7308 Intermediate Similarity NPD5353 Approved
0.7297 Intermediate Similarity NPD4236 Phase 3
0.7297 Intermediate Similarity NPD4237 Approved
0.7296 Intermediate Similarity NPD1247 Approved
0.7293 Intermediate Similarity NPD7157 Approved
0.7292 Intermediate Similarity NPD6355 Discontinued
0.7292 Intermediate Similarity NPD3657 Discovery
0.7287 Intermediate Similarity NPD2684 Approved
0.7284 Intermediate Similarity NPD3818 Discontinued
0.7279 Intermediate Similarity NPD7266 Discontinued
0.7279 Intermediate Similarity NPD17 Approved
0.7278 Intermediate Similarity NPD919 Approved
0.7254 Intermediate Similarity NPD7095 Approved
0.7246 Intermediate Similarity NPD3972 Approved
0.7244 Intermediate Similarity NPD2801 Approved
0.7241 Intermediate Similarity NPD6653 Approved
0.7234 Intermediate Similarity NPD9494 Approved
0.7222 Intermediate Similarity NPD3619 Clinical (unspecified phase)
0.7222 Intermediate Similarity NPD3620 Phase 2
0.7222 Intermediate Similarity NPD2979 Phase 3
0.7219 Intermediate Similarity NPD5297 Approved
0.7205 Intermediate Similarity NPD5242 Approved
0.7203 Intermediate Similarity NPD5111 Phase 2
0.7203 Intermediate Similarity NPD5109 Approved
0.7203 Intermediate Similarity NPD5110 Phase 2
0.72 Intermediate Similarity NPD6190 Approved
0.7197 Intermediate Similarity NPD7843 Approved
0.7194 Intermediate Similarity NPD5327 Phase 3
0.7188 Intermediate Similarity NPD7199 Phase 2
0.7183 Intermediate Similarity NPD1529 Clinical (unspecified phase)
0.716 Intermediate Similarity NPD6166 Phase 2
0.716 Intermediate Similarity NPD6168 Clinical (unspecified phase)
0.716 Intermediate Similarity NPD6167 Clinical (unspecified phase)
0.7153 Intermediate Similarity NPD4626 Approved
0.7152 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.7143 Intermediate Similarity NPD8651 Approved
0.7143 Intermediate Similarity NPD1653 Approved
0.7143 Intermediate Similarity NPD3748 Approved
0.7134 Intermediate Similarity NPD5844 Phase 1
0.7133 Intermediate Similarity NPD8166 Discontinued
0.7133 Intermediate Similarity NPD6398 Clinical (unspecified phase)
0.7122 Intermediate Similarity NPD1608 Approved
0.7113 Intermediate Similarity NPD1530 Clinical (unspecified phase)
0.7108 Intermediate Similarity NPD7685 Pre-registration
0.7103 Intermediate Similarity NPD4060 Phase 1
0.7101 Intermediate Similarity NPD3496 Discontinued
0.7099 Intermediate Similarity NPD7184 Clinical (unspecified phase)
0.7097 Intermediate Similarity NPD6055 Clinical (unspecified phase)
0.7097 Intermediate Similarity NPD3866 Clinical (unspecified phase)
0.7095 Intermediate Similarity NPD2161 Phase 2
0.7075 Intermediate Similarity NPD7097 Phase 1
0.7075 Intermediate Similarity NPD6111 Discontinued
0.7073 Intermediate Similarity NPD7228 Approved
0.7071 Intermediate Similarity NPD4359 Approved
0.7071 Intermediate Similarity NPD4749 Approved
0.7068 Intermediate Similarity NPD5535 Approved
0.7067 Intermediate Similarity NPD6674 Discontinued
0.7063 Intermediate Similarity NPD4908 Phase 1
0.7063 Intermediate Similarity NPD5752 Clinical (unspecified phase)
0.7059 Intermediate Similarity NPD3146 Approved
0.7059 Intermediate Similarity NPD3688 Clinical (unspecified phase)
0.7055 Intermediate Similarity NPD447 Suspended
0.7055 Intermediate Similarity NPD230 Phase 1
0.7051 Intermediate Similarity NPD4380 Phase 2
0.705 Intermediate Similarity NPD1281 Approved
0.7047 Intermediate Similarity NPD6002 Phase 3
0.7047 Intermediate Similarity NPD5763 Approved
0.7047 Intermediate Similarity NPD5762 Approved
0.7047 Intermediate Similarity NPD6003 Clinical (unspecified phase)
0.7047 Intermediate Similarity NPD6006 Clinical (unspecified phase)
0.7047 Intermediate Similarity NPD6004 Phase 3
0.7047 Intermediate Similarity NPD6005 Phase 3
0.7039 Intermediate Similarity NPD7124 Phase 2
0.7034 Intermediate Similarity NPD8032 Phase 2
0.7034 Intermediate Similarity NPD6233 Phase 2
0.7034 Intermediate Similarity NPD1726 Clinical (unspecified phase)
0.7032 Intermediate Similarity NPD3686 Approved
0.7032 Intermediate Similarity NPD3687 Approved
0.7027 Intermediate Similarity NPD6029 Clinical (unspecified phase)
0.7027 Intermediate Similarity NPD6028 Clinical (unspecified phase)
0.702 Intermediate Similarity NPD6331 Phase 2
0.7012 Intermediate Similarity NPD7473 Discontinued
0.7007 Intermediate Similarity NPD2492 Phase 1
0.7007 Intermediate Similarity NPD2653 Approved
0.7006 Intermediate Similarity NPD6873 Phase 2
0.7006 Intermediate Similarity NPD5089 Approved
0.7006 Intermediate Similarity NPD5090 Approved
0.6993 Remote Similarity NPD6799 Approved
0.6993 Remote Similarity NPD1511 Approved
0.6988 Remote Similarity NPD7074 Phase 3
0.6986 Remote Similarity NPD4140 Approved
0.6986 Remote Similarity NPD2238 Phase 2
0.6981 Remote Similarity NPD2560 Approved
0.6981 Remote Similarity NPD5977 Approved
0.6981 Remote Similarity NPD2563 Approved
0.6981 Remote Similarity NPD5978 Approved
0.698 Remote Similarity NPD2935 Discontinued
0.6974 Remote Similarity NPD3887 Approved
0.6972 Remote Similarity NPD3266 Approved
0.6972 Remote Similarity NPD3267 Approved
0.697 Remote Similarity NPD3021 Approved
0.697 Remote Similarity NPD3022 Approved
0.6966 Remote Similarity NPD4907 Clinical (unspecified phase)
0.6966 Remote Similarity NPD3764 Approved
0.6966 Remote Similarity NPD6410 Clinical (unspecified phase)
0.6966 Remote Similarity NPD6798 Discontinued
0.6966 Remote Similarity NPD6859 Clinical (unspecified phase)
0.6959 Remote Similarity NPD6896 Approved
0.6959 Remote Similarity NPD6895 Approved
0.6954 Remote Similarity NPD5698 Clinical (unspecified phase)
0.6954 Remote Similarity NPD7421 Clinical (unspecified phase)
0.6951 Remote Similarity NPD4481 Phase 3
0.6943 Remote Similarity NPD6599 Discontinued
0.6939 Remote Similarity NPD1933 Approved
0.6939 Remote Similarity NPD5123 Clinical (unspecified phase)
0.6939 Remote Similarity NPD5735 Approved
0.6939 Remote Similarity NPD5124 Phase 1
0.6937 Remote Similarity NPD5019 Clinical (unspecified phase)
0.6933 Remote Similarity NPD6232 Discontinued
0.6929 Remote Similarity NPD1547 Clinical (unspecified phase)
0.6929 Remote Similarity NPD1610 Phase 2
0.6928 Remote Similarity NPD7054 Approved
0.6928 Remote Similarity NPD5058 Phase 3
0.6923 Remote Similarity NPD2798 Approved
0.6923 Remote Similarity NPD6917 Clinical (unspecified phase)
0.6918 Remote Similarity NPD7096 Clinical (unspecified phase)
0.6918 Remote Similarity NPD7819 Suspended
0.6918 Remote Similarity NPD4870 Approved
0.6918 Remote Similarity NPD4585 Approved
0.6913 Remote Similarity NPD7033 Discontinued
0.6913 Remote Similarity NPD5588 Approved
0.6913 Remote Similarity NPD2799 Discontinued
0.6913 Remote Similarity NPD1510 Phase 2
0.6912 Remote Similarity NPD6671 Approved
0.6908 Remote Similarity NPD6658 Clinical (unspecified phase)
0.6908 Remote Similarity NPD3750 Approved
0.6906 Remote Similarity NPD1778 Approved
0.6905 Remote Similarity NPD7240 Approved
0.6903 Remote Similarity NPD1940 Clinical (unspecified phase)
0.6903 Remote Similarity NPD7526 Approved
0.6903 Remote Similarity NPD7527 Clinical (unspecified phase)
0.6903 Remote Similarity NPD1512 Approved
0.6903 Remote Similarity NPD52 Approved
0.6903 Remote Similarity NPD6273 Approved
0.6901 Remote Similarity NPD1283 Approved
0.6887 Remote Similarity NPD970 Clinical (unspecified phase)
0.6887 Remote Similarity NPD1549 Phase 2
0.6886 Remote Similarity NPD7472 Approved
0.6875 Remote Similarity NPD6374 Clinical (unspecified phase)
0.6871 Remote Similarity NPD1240 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