Structure

Physi-Chem Properties

Molecular Weight:  416.11
Volume:  395.567
LogP:  2.869
LogD:  2.935
LogS:  -4.732
# Rotatable Bonds:  6
TPSA:  94.82
# H-Bond Aceptor:  9
# H-Bond Donor:  0
# Rings:  4
# Heavy Atoms:  9

MedChem Properties

QED Drug-Likeness Score:  0.6
Synthetic Accessibility Score:  2.676
Fsp3:  0.286
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.555
MDCK Permeability:  2.2776886908104643e-05
Pgp-inhibitor:  1.0
Pgp-substrate:  0.0
Human Intestinal Absorption (HIA):  0.007
20% Bioavailability (F20%):  0.0
30% Bioavailability (F30%):  0.001

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.035
Plasma Protein Binding (PPB):  73.83110809326172%
Volume Distribution (VD):  0.983
Pgp-substrate:  23.59393310546875%

ADMET: Metabolism

CYP1A2-inhibitor:  0.271
CYP1A2-substrate:  0.982
CYP2C19-inhibitor:  0.899
CYP2C19-substrate:  0.856
CYP2C9-inhibitor:  0.833
CYP2C9-substrate:  0.925
CYP2D6-inhibitor:  0.014
CYP2D6-substrate:  0.892
CYP3A4-inhibitor:  0.835
CYP3A4-substrate:  0.756

ADMET: Excretion

Clearance (CL):  4.817
Half-life (T1/2):  0.296

ADMET: Toxicity

hERG Blockers:  0.291
Human Hepatotoxicity (H-HT):  0.083
Drug-inuced Liver Injury (DILI):  0.978
AMES Toxicity:  0.348
Rat Oral Acute Toxicity:  0.174
Maximum Recommended Daily Dose:  0.017
Skin Sensitization:  0.228
Carcinogencity:  0.871
Eye Corrosion:  0.003
Eye Irritation:  0.204
Respiratory Toxicity:  0.047

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

  Natural Product: NPC257914

Natural Product ID:  NPC257914
Common Name*:   2-(1,3-Benzodioxol-5-Yl)-3,5,6,7,8-Pentamethoxychromen-4-One
IUPAC Name:   2-(1,3-benzodioxol-5-yl)-3,5,6,7,8-pentamethoxychromen-4-one
Synonyms:  
Standard InCHIKey:  CRSVEURWRGBEIE-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C21H20O9/c1-23-16-13-14(22)18(24-2)15(10-6-7-11-12(8-10)29-9-28-11)30-17(13)20(26-4)21(27-5)19(16)25-3/h6-8H,9H2,1-5H3
SMILES:  COc1c(OC)c2oc(c3ccc4c(c3)OCO4)c(c(=O)c2c(c1OC)OC)OC
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL1976139
PubChem CID:   386323
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000261] Phenylpropanoids and polyketides
      • [CHEMONTID:0000334] Flavonoids
        • [CHEMONTID:0002585] O-methylated flavonoids
          • [CHEMONTID:0002593] 8-O-methylated 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
NPO7058 Australostichopus mollis Species Stichopodidae Eukaryota n.a. n.a. n.a. PMID[15974605]
NPO7058 Australostichopus mollis Species Stichopodidae Eukaryota n.a. n.a. n.a. PMID[22271309]
NPO1879 Feijoa sellowiana Species Myrtaceae Eukaryota Fruit n.a. n.a. Database[FooDB]
NPO1879 Feijoa sellowiana Species Myrtaceae Eukaryota n.a. n.a. Database[FooDB]
NPO1879 Feijoa sellowiana Species Myrtaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO22038 Lagarostrobos franklinii Species Podocarpaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18403 Lagochilus platycalyx Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1879 Feijoa sellowiana Species Myrtaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22034 Eysenhardtia texana Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19147 Rhodiola pamiroalaica Species Crassulaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18490 Spiraea kamtschatica Species Rosaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18742 Cereus longispinus Species Sagartiidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14576 Trichoderma atroviride Species Hypocreaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18652 Melicope broadbentiana Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7058 Australostichopus mollis Species Stichopodidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17564 Puccinia arachidis Species Pucciniaceae 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
NPT368 Cell Line SN12C Homo sapiens GI50 n.a. 100000.0 nM PMID[522407]
NPT367 Cell Line MDA-N Homo sapiens GI50 n.a. 100000.0 nM PMID[522407]
NPT370 Cell Line NCI-H23 Homo sapiens GI50 n.a. 100000.0 nM PMID[522407]
NPT371 Cell Line UO-31 Homo sapiens GI50 n.a. 57809.6 nM PMID[522407]
NPT369 Cell Line ACHN Homo sapiens GI50 n.a. 68706.84 nM PMID[522407]
NPT116 Cell Line HL-60 Homo sapiens GI50 n.a. 11561.12 nM PMID[522407]
NPT372 Cell Line HOP-92 Homo sapiens GI50 n.a. 1482.52 nM PMID[522407]
NPT374 Cell Line SF-539 Homo sapiens GI50 n.a. 100000.0 nM PMID[522407]
NPT90 Cell Line DU-145 Homo sapiens GI50 n.a. 100000.0 nM PMID[522407]
NPT373 Cell Line SK-MEL-5 Homo sapiens GI50 n.a. 44771.33 nM PMID[522407]
NPT375 Cell Line Malme-3M Homo sapiens GI50 n.a. 100000.0 nM PMID[522407]
NPT376 Cell Line A498 Homo sapiens GI50 n.a. 66221.65 nM PMID[522407]
NPT111 Cell Line K562 Homo sapiens GI50 n.a. 64714.26 nM PMID[522407]
NPT377 Cell Line OVCAR-3 Homo sapiens GI50 n.a. 100000.0 nM PMID[522407]
NPT112 Cell Line MOLT-4 Homo sapiens GI50 n.a. 39719.15 nM PMID[522407]
NPT379 Cell Line HOP-62 Homo sapiens GI50 n.a. 100000.0 nM PMID[522407]
NPT378 Cell Line NCI/ADR-RES Homo sapiens GI50 n.a. 86896.04 nM PMID[522407]
NPT380 Cell Line U-251 Homo sapiens GI50 n.a. 100000.0 nM PMID[522407]
NPT382 Cell Line OVCAR-5 Homo sapiens GI50 n.a. 100000.0 nM PMID[522407]
NPT381 Cell Line OVCAR-8 Homo sapiens GI50 n.a. 60953.69 nM PMID[522407]
NPT383 Cell Line SNB-19 Homo sapiens GI50 n.a. 100000.0 nM PMID[522407]
NPT82 Cell Line MDA-MB-231 Homo sapiens GI50 n.a. 100000.0 nM PMID[522407]
NPT384 Cell Line TK-10 Homo sapiens GI50 n.a. 100000.0 nM PMID[522407]
NPT323 Cell Line SW-620 Homo sapiens GI50 n.a. 100000.0 nM PMID[522407]
NPT455 Cell Line NCI-H522 Homo sapiens GI50 n.a. 100000.0 nM PMID[522407]
NPT386 Cell Line KM12 Homo sapiens GI50 n.a. 100000.0 nM PMID[522407]
NPT387 Cell Line M14 Homo sapiens GI50 n.a. 100000.0 nM PMID[522407]
NPT388 Cell Line NCI-H322M Homo sapiens GI50 n.a. 100000.0 nM PMID[522407]
NPT456 Cell Line OVCAR-4 Homo sapiens GI50 n.a. 100000.0 nM PMID[522407]
NPT390 Cell Line LOX IMVI Homo sapiens GI50 n.a. 100000.0 nM PMID[522407]
NPT457 Cell Line BT-549 Homo sapiens GI50 n.a. 100000.0 nM PMID[522407]
NPT147 Cell Line SK-MEL-2 Homo sapiens GI50 n.a. 100000.0 nM PMID[522407]
NPT81 Cell Line A549 Homo sapiens GI50 n.a. 53210.83 nM PMID[522407]
NPT391 Cell Line HCC 2998 Homo sapiens GI50 n.a. 100000.0 nM PMID[522407]
NPT392 Cell Line SNB-75 Homo sapiens GI50 n.a. 65313.06 nM PMID[522407]
NPT148 Cell Line HCT-15 Homo sapiens GI50 n.a. 78523.56 nM PMID[522407]
NPT393 Cell Line HCT-116 Homo sapiens GI50 n.a. 86696.19 nM PMID[522407]
NPT395 Cell Line SF-268 Homo sapiens GI50 n.a. 100000.0 nM PMID[522407]
NPT83 Cell Line MCF7 Homo sapiens GI50 n.a. 100000.0 nM PMID[522407]
NPT394 Cell Line EKVX Homo sapiens GI50 n.a. 82794.22 nM PMID[522407]
NPT306 Cell Line PC-3 Homo sapiens GI50 n.a. 69183.1 nM PMID[522407]
NPT146 Cell Line SK-OV-3 Homo sapiens GI50 n.a. 100000.0 nM PMID[522407]
NPT397 Cell Line NCI-H460 Homo sapiens GI50 n.a. 100000.0 nM PMID[522407]
NPT396 Cell Line T47D Homo sapiens GI50 n.a. 41879.36 nM PMID[522407]
NPT398 Cell Line UACC-62 Homo sapiens GI50 n.a. 100000.0 nM PMID[522407]
NPT400 Cell Line MDA-MB-435 Homo sapiens GI50 n.a. 82413.81 nM PMID[522407]
NPT308 Cell Line CAKI-1 Homo sapiens GI50 n.a. 100000.0 nM PMID[522407]
NPT458 Cell Line IGROV-1 Homo sapiens GI50 n.a. 100000.0 nM PMID[522407]
NPT399 Cell Line SF-295 Homo sapiens GI50 n.a. 100000.0 nM PMID[522407]
NPT402 Cell Line Hs-578T Homo sapiens GI50 n.a. 100000.0 nM PMID[522407]
NPT403 Cell Line UACC-257 Homo sapiens GI50 n.a. 100000.0 nM PMID[522407]
NPT401 Cell Line 786-0 Homo sapiens GI50 n.a. 100000.0 nM PMID[522407]
NPT404 Cell Line CCRF-CEM Homo sapiens GI50 n.a. 23823.19 nM PMID[522407]
NPT405 Cell Line NCI-H226 Homo sapiens GI50 n.a. 100000.0 nM PMID[522407]
NPT170 Cell Line SK-MEL-28 Homo sapiens GI50 n.a. 100000.0 nM PMID[522407]
NPT139 Cell Line HT-29 Homo sapiens GI50 n.a. 100000.0 nM PMID[522407]
NPT406 Cell Line RXF 393 Homo sapiens GI50 n.a. 100000.0 nM PMID[522407]
NPT407 Cell Line COLO 205 Homo sapiens GI50 n.a. 100000.0 nM PMID[522407]
NPT2 Others Unspecified Ki = 76500.0 nM PMID[522408]

☑ 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 NPC257914 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 NPC104459
1.0 High Similarity NPC238405
0.9803 High Similarity NPC131557
0.9669 High Similarity NPC284353
0.9667 High Similarity NPC292460
0.9603 High Similarity NPC279930
0.9554 High Similarity NPC76482
0.9533 High Similarity NPC201547
0.9533 High Similarity NPC259058
0.9467 High Similarity NPC181250
0.9467 High Similarity NPC69752
0.9416 High Similarity NPC258644
0.9412 High Similarity NPC122623
0.9412 High Similarity NPC241774
0.9412 High Similarity NPC276059
0.9412 High Similarity NPC34725
0.9367 High Similarity NPC113093
0.9351 High Similarity NPC257277
0.9346 High Similarity NPC244371
0.9346 High Similarity NPC478213
0.9346 High Similarity NPC57211
0.9333 High Similarity NPC85233
0.9299 High Similarity NPC302741
0.9295 High Similarity NPC269906
0.9281 High Similarity NPC134677
0.9281 High Similarity NPC148497
0.9281 High Similarity NPC52623
0.9281 High Similarity NPC153008
0.9281 High Similarity NPC68882
0.9267 High Similarity NPC283002
0.9267 High Similarity NPC310259
0.9267 High Similarity NPC215932
0.9267 High Similarity NPC302408
0.9267 High Similarity NPC110639
0.9267 High Similarity NPC106461
0.9267 High Similarity NPC14958
0.9267 High Similarity NPC40818
0.9226 High Similarity NPC178854
0.9216 High Similarity NPC474388
0.9216 High Similarity NPC474170
0.9216 High Similarity NPC472535
0.9216 High Similarity NPC279061
0.9205 High Similarity NPC205522
0.9205 High Similarity NPC117463
0.9205 High Similarity NPC299923
0.92 High Similarity NPC165512
0.9182 High Similarity NPC187923
0.9177 High Similarity NPC18284
0.9177 High Similarity NPC273021
0.9167 High Similarity NPC310206
0.9161 High Similarity NPC478238
0.9161 High Similarity NPC189960
0.9161 High Similarity NPC32557
0.915 High Similarity NPC177839
0.9133 High Similarity NPC23955
0.9108 High Similarity NPC7846
0.9108 High Similarity NPC204854
0.9108 High Similarity NPC4481
0.9108 High Similarity NPC152166
0.9108 High Similarity NPC25495
0.9108 High Similarity NPC261004
0.9108 High Similarity NPC18607
0.9108 High Similarity NPC191459
0.9108 High Similarity NPC288669
0.9108 High Similarity NPC130894
0.9108 High Similarity NPC9609
0.9108 High Similarity NPC300943
0.9108 High Similarity NPC18772
0.9108 High Similarity NPC176300
0.9108 High Similarity NPC253634
0.9108 High Similarity NPC22472
0.9108 High Similarity NPC115798
0.9108 High Similarity NPC143828
0.9108 High Similarity NPC105242
0.9108 High Similarity NPC19687
0.9103 High Similarity NPC155063
0.9097 High Similarity NPC246204
0.9097 High Similarity NPC476289
0.9097 High Similarity NPC86485
0.908 High Similarity NPC169977
0.908 High Similarity NPC45522
0.908 High Similarity NPC42773
0.908 High Similarity NPC101026
0.908 High Similarity NPC21666
0.908 High Similarity NPC24043
0.9073 High Similarity NPC136278
0.9073 High Similarity NPC296575
0.9067 High Similarity NPC70853
0.9067 High Similarity NPC9966
0.9057 High Similarity NPC478199
0.9045 High Similarity NPC235215
0.9045 High Similarity NPC305663
0.9045 High Similarity NPC224137
0.9045 High Similarity NPC163524
0.9045 High Similarity NPC110070
0.9045 High Similarity NPC189179
0.9045 High Similarity NPC7973
0.9045 High Similarity NPC176665
0.9045 High Similarity NPC93376
0.9045 High Similarity NPC75215
0.9045 High Similarity NPC227192
0.9045 High Similarity NPC203891
0.9045 High Similarity NPC78302
0.9045 High Similarity NPC472438
0.9045 High Similarity NPC101830
0.9045 High Similarity NPC287979
0.9045 High Similarity NPC29841
0.9036 High Similarity NPC473073
0.9036 High Similarity NPC473071
0.9032 High Similarity NPC301123
0.9024 High Similarity NPC264735
0.902 High Similarity NPC63256
0.902 High Similarity NPC10304
0.902 High Similarity NPC261548
0.9018 High Similarity NPC476405
0.9018 High Similarity NPC117260
0.9012 High Similarity NPC476771
0.9007 High Similarity NPC113089
0.9006 High Similarity NPC475214
0.9006 High Similarity NPC255615
0.9006 High Similarity NPC254306
0.9006 High Similarity NPC67037
0.9 High Similarity NPC124467
0.9 High Similarity NPC214919
0.9 High Similarity NPC29536
0.8994 High Similarity NPC34376
0.8987 High Similarity NPC113055
0.8987 High Similarity NPC195832
0.8987 High Similarity NPC193842
0.8987 High Similarity NPC62518
0.8987 High Similarity NPC215375
0.8982 High Similarity NPC473072
0.8981 High Similarity NPC292107
0.8981 High Similarity NPC98661
0.8981 High Similarity NPC200388
0.8981 High Similarity NPC247017
0.8981 High Similarity NPC266960
0.8981 High Similarity NPC268161
0.8981 High Similarity NPC43243
0.8981 High Similarity NPC100916
0.8981 High Similarity NPC55619
0.8981 High Similarity NPC245546
0.8981 High Similarity NPC474520
0.8981 High Similarity NPC49824
0.8974 High Similarity NPC186507
0.897 High Similarity NPC198324
0.897 High Similarity NPC472385
0.8968 High Similarity NPC208043
0.8968 High Similarity NPC236769
0.8968 High Similarity NPC76376
0.8968 High Similarity NPC226973
0.8961 High Similarity NPC238366
0.8957 High Similarity NPC72249
0.8957 High Similarity NPC282987
0.8957 High Similarity NPC84265
0.8957 High Similarity NPC245014
0.8951 High Similarity NPC42892
0.8951 High Similarity NPC135345
0.8947 High Similarity NPC224687
0.8944 High Similarity NPC34531
0.8944 High Similarity NPC280893
0.8938 High Similarity NPC469575
0.8924 High Similarity NPC19097
0.8924 High Similarity NPC167595
0.8917 High Similarity NPC280339
0.8917 High Similarity NPC50715
0.8917 High Similarity NPC2476
0.8917 High Similarity NPC18954
0.8917 High Similarity NPC128863
0.8917 High Similarity NPC26227
0.8917 High Similarity NPC183597
0.8917 High Similarity NPC44079
0.8917 High Similarity NPC227325
0.8917 High Similarity NPC163780
0.8917 High Similarity NPC201136
0.8917 High Similarity NPC196439
0.8917 High Similarity NPC92659
0.8917 High Similarity NPC167815
0.8917 High Similarity NPC214138
0.8917 High Similarity NPC201451
0.8917 High Similarity NPC4455
0.8917 High Similarity NPC471746
0.8917 High Similarity NPC146165
0.8917 High Similarity NPC138360
0.8916 High Similarity NPC168584
0.8909 High Similarity NPC49344
0.8909 High Similarity NPC210094
0.8909 High Similarity NPC135277
0.8909 High Similarity NPC43211
0.8909 High Similarity NPC101191
0.8909 High Similarity NPC237435
0.8909 High Similarity NPC477848
0.8909 High Similarity NPC115760
0.8903 High Similarity NPC306821
0.8903 High Similarity NPC219330
0.8903 High Similarity NPC50728
0.8903 High Similarity NPC166753
0.8902 High Similarity NPC245452
0.8902 High Similarity NPC476772
0.8902 High Similarity NPC475825

  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 NPC257914 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
0.9038 High Similarity NPD3817 Phase 2
0.8909 High Similarity NPD4338 Clinical (unspecified phase)
0.8854 High Similarity NPD2801 Approved
0.8834 High Similarity NPD3818 Discontinued
0.8742 High Similarity NPD3882 Suspended
0.8696 High Similarity NPD5494 Approved
0.8683 High Similarity NPD7808 Phase 3
0.8675 High Similarity NPD6797 Phase 2
0.8642 High Similarity NPD1247 Approved
0.8623 High Similarity NPD7251 Discontinued
0.859 High Similarity NPD6980 Clinical (unspecified phase)
0.8554 High Similarity NPD7054 Approved
0.8503 High Similarity NPD7472 Approved
0.8424 Intermediate Similarity NPD3926 Phase 2
0.8408 Intermediate Similarity NPD1512 Approved
0.8405 Intermediate Similarity NPD919 Approved
0.8393 Intermediate Similarity NPD7074 Phase 3
0.8333 Intermediate Similarity NPD5402 Approved
0.8323 Intermediate Similarity NPD1934 Approved
0.828 Intermediate Similarity NPD1511 Approved
0.828 Intermediate Similarity NPD6799 Approved
0.8263 Intermediate Similarity NPD6168 Clinical (unspecified phase)
0.8263 Intermediate Similarity NPD6166 Phase 2
0.8263 Intermediate Similarity NPD6167 Clinical (unspecified phase)
0.8232 Intermediate Similarity NPD4381 Clinical (unspecified phase)
0.8228 Intermediate Similarity NPD4378 Clinical (unspecified phase)
0.8225 Intermediate Similarity NPD7804 Clinical (unspecified phase)
0.8182 Intermediate Similarity NPD2796 Approved
0.816 Intermediate Similarity NPD2393 Clinical (unspecified phase)
0.8098 Intermediate Similarity NPD6801 Discontinued
0.8095 Intermediate Similarity NPD7184 Clinical (unspecified phase)
0.8049 Intermediate Similarity NPD7096 Clinical (unspecified phase)
0.8012 Intermediate Similarity NPD7075 Discontinued
0.7975 Intermediate Similarity NPD6599 Discontinued
0.7929 Intermediate Similarity NPD6232 Discontinued
0.7922 Intermediate Similarity NPD1933 Approved
0.7901 Intermediate Similarity NPD5403 Approved
0.7895 Intermediate Similarity NPD7473 Discontinued
0.7888 Intermediate Similarity NPD5401 Approved
0.7874 Intermediate Similarity NPD6559 Discontinued
0.787 Intermediate Similarity NPD7199 Phase 2
0.7844 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.7831 Intermediate Similarity NPD7819 Suspended
0.7826 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.7791 Intermediate Similarity NPD920 Approved
0.7758 Intermediate Similarity NPD4380 Phase 2
0.7719 Intermediate Similarity NPD3787 Discontinued
0.7701 Intermediate Similarity NPD5844 Phase 1
0.7688 Intermediate Similarity NPD1243 Approved
0.7673 Intermediate Similarity NPD1550 Clinical (unspecified phase)
0.7673 Intermediate Similarity NPD1552 Clinical (unspecified phase)
0.7669 Intermediate Similarity NPD642 Clinical (unspecified phase)
0.7669 Intermediate Similarity NPD7410 Clinical (unspecified phase)
0.7665 Intermediate Similarity NPD37 Approved
0.7658 Intermediate Similarity NPD1510 Phase 2
0.7644 Intermediate Similarity NPD3751 Discontinued
0.7633 Intermediate Similarity NPD4966 Approved
0.7633 Intermediate Similarity NPD4965 Approved
0.7633 Intermediate Similarity NPD4967 Phase 2
0.7625 Intermediate Similarity NPD1549 Phase 2
0.7614 Intermediate Similarity NPD7993 Clinical (unspecified phase)
0.7605 Intermediate Similarity NPD7411 Suspended
0.7582 Intermediate Similarity NPD7879 Clinical (unspecified phase)
0.7547 Intermediate Similarity NPD3748 Approved
0.7546 Intermediate Similarity NPD643 Clinical (unspecified phase)
0.7544 Intermediate Similarity NPD6234 Discontinued
0.753 Intermediate Similarity NPD1653 Approved
0.7529 Intermediate Similarity NPD2403 Approved
0.7516 Intermediate Similarity NPD1240 Approved
0.7516 Intermediate Similarity NPD970 Clinical (unspecified phase)
0.7515 Intermediate Similarity NPD1465 Phase 2
0.75 Intermediate Similarity NPD8055 Clinical (unspecified phase)
0.7471 Intermediate Similarity NPD8443 Clinical (unspecified phase)
0.7468 Intermediate Similarity NPD447 Suspended
0.7423 Intermediate Similarity NPD1878 Clinical (unspecified phase)
0.7421 Intermediate Similarity NPD1607 Approved
0.7391 Intermediate Similarity NPD2935 Discontinued
0.7389 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.7384 Intermediate Similarity NPD3749 Approved
0.7377 Intermediate Similarity NPD8397 Clinical (unspecified phase)
0.7372 Intermediate Similarity NPD6832 Phase 2
0.7362 Intermediate Similarity NPD2800 Approved
0.7356 Intermediate Similarity NPD6959 Discontinued
0.7349 Intermediate Similarity NPD2534 Approved
0.7349 Intermediate Similarity NPD2532 Approved
0.7349 Intermediate Similarity NPD2533 Approved
0.733 Intermediate Similarity NPD7784 Clinical (unspecified phase)
0.7317 Intermediate Similarity NPD3750 Approved
0.7296 Intermediate Similarity NPD943 Approved
0.7278 Intermediate Similarity NPD7685 Pre-registration
0.7273 Intermediate Similarity NPD6190 Approved
0.7273 Intermediate Similarity NPD5242 Approved
0.7256 Intermediate Similarity NPD2654 Approved
0.725 Intermediate Similarity NPD1899 Clinical (unspecified phase)
0.7247 Intermediate Similarity NPD7228 Approved
0.7244 Intermediate Similarity NPD2798 Approved
0.7239 Intermediate Similarity NPD1471 Phase 3
0.7232 Intermediate Similarity NPD7852 Clinical (unspecified phase)
0.7225 Intermediate Similarity NPD5006 Approved
0.7225 Intermediate Similarity NPD5005 Approved
0.7211 Intermediate Similarity NPD6777 Approved
0.7211 Intermediate Similarity NPD6780 Approved
0.7211 Intermediate Similarity NPD6781 Approved
0.7211 Intermediate Similarity NPD6778 Approved
0.7211 Intermediate Similarity NPD6782 Approved
0.7211 Intermediate Similarity NPD6779 Approved
0.7211 Intermediate Similarity NPD6776 Approved
0.7193 Intermediate Similarity NPD6386 Approved
0.7193 Intermediate Similarity NPD6385 Approved
0.7188 Intermediate Similarity NPD7435 Discontinued
0.7178 Intermediate Similarity NPD1551 Phase 2
0.7176 Intermediate Similarity NPD3226 Approved
0.7174 Intermediate Similarity NPD8434 Phase 2
0.717 Intermediate Similarity NPD2313 Discontinued
0.7168 Intermediate Similarity NPD5353 Approved
0.7152 Intermediate Similarity NPD7421 Clinical (unspecified phase)
0.7143 Intermediate Similarity NPD3705 Approved
0.7143 Intermediate Similarity NPD230 Phase 1
0.7134 Intermediate Similarity NPD2344 Approved
0.7126 Intermediate Similarity NPD7768 Phase 2
0.7125 Intermediate Similarity NPD6233 Phase 2
0.7117 Intermediate Similarity NPD2799 Discontinued
0.7117 Intermediate Similarity NPD651 Clinical (unspecified phase)
0.7105 Intermediate Similarity NPD4420 Approved
0.7098 Intermediate Similarity NPD7698 Approved
0.7098 Intermediate Similarity NPD7697 Approved
0.7098 Intermediate Similarity NPD7696 Phase 3
0.7089 Intermediate Similarity NPD3018 Phase 2
0.7088 Intermediate Similarity NPD7240 Approved
0.7062 Intermediate Similarity NPD7871 Phase 2
0.7062 Intermediate Similarity NPD7870 Phase 2
0.7049 Intermediate Similarity NPD4419 Clinical (unspecified phase)
0.7044 Intermediate Similarity NPD1529 Clinical (unspecified phase)
0.7041 Intermediate Similarity NPD3688 Clinical (unspecified phase)
0.7041 Intermediate Similarity NPD3146 Approved
0.7039 Intermediate Similarity NPD5536 Phase 2
0.7033 Intermediate Similarity NPD5953 Discontinued
0.7032 Intermediate Similarity NPD1547 Clinical (unspecified phase)
0.7031 Intermediate Similarity NPD7501 Clinical (unspecified phase)
0.703 Intermediate Similarity NPD2346 Discontinued
0.7011 Intermediate Similarity NPD8313 Approved
0.7011 Intermediate Similarity NPD8312 Approved
0.7006 Intermediate Similarity NPD4628 Phase 3
0.7 Intermediate Similarity NPD1940 Clinical (unspecified phase)
0.6987 Remote Similarity NPD2981 Phase 2
0.6981 Remote Similarity NPD1530 Clinical (unspecified phase)
0.6975 Remote Similarity NPD1612 Clinical (unspecified phase)
0.6975 Remote Similarity NPD1613 Approved
0.697 Remote Similarity NPD7874 Approved
0.697 Remote Similarity NPD7875 Clinical (unspecified phase)
0.6964 Remote Similarity NPD3887 Approved
0.6964 Remote Similarity NPD2309 Approved
0.6963 Remote Similarity NPD8090 Clinical (unspecified phase)
0.6962 Remote Similarity NPD3266 Approved
0.6962 Remote Similarity NPD3267 Approved
0.6961 Remote Similarity NPD2163 Approved
0.6957 Remote Similarity NPD6798 Discontinued
0.6954 Remote Similarity NPD7701 Phase 2
0.6954 Remote Similarity NPD6844 Discontinued
0.6949 Remote Similarity NPD5537 Clinical (unspecified phase)
0.6947 Remote Similarity NPD6534 Approved
0.6947 Remote Similarity NPD6535 Approved
0.6943 Remote Similarity NPD2982 Phase 2
0.6943 Remote Similarity NPD5457 Discontinued
0.6943 Remote Similarity NPD2983 Phase 2
0.6933 Remote Similarity NPD6355 Discontinued
0.6932 Remote Similarity NPD5019 Clinical (unspecified phase)
0.6928 Remote Similarity NPD2355 Clinical (unspecified phase)
0.6928 Remote Similarity NPD2353 Approved
0.6927 Remote Similarity NPD7229 Phase 3
0.6923 Remote Similarity NPD7286 Phase 2
0.6909 Remote Similarity NPD7033 Discontinued
0.6904 Remote Similarity NPD7584 Approved
0.6903 Remote Similarity NPD17 Approved
0.6894 Remote Similarity NPD3027 Phase 3
0.689 Remote Similarity NPD6651 Approved
0.6879 Remote Similarity NPD7458 Discontinued
0.6871 Remote Similarity NPD4307 Phase 2
0.6867 Remote Similarity NPD6100 Approved
0.6867 Remote Similarity NPD6099 Approved
0.6855 Remote Similarity NPD1203 Approved
0.6852 Remote Similarity NPD3268 Approved
0.6852 Remote Similarity NPD1296 Phase 2
0.685 Remote Similarity NPD7782 Clinical (unspecified phase)
0.685 Remote Similarity NPD7783 Phase 2
0.685 Remote Similarity NPD7801 Approved
0.6839 Remote Similarity NPD7700 Phase 2
0.6839 Remote Similarity NPD7028 Phase 2
0.6839 Remote Similarity NPD7699 Phase 2
0.6834 Remote Similarity NPD8151 Discontinued
0.6833 Remote Similarity NPD5710 Approved
0.6833 Remote Similarity NPD5711 Approved
0.6818 Remote Similarity NPD8455 Phase 2
0.6813 Remote Similarity NPD1019 Discontinued
0.6807 Remote Similarity NPD1509 Clinical (unspecified phase)
0.6786 Remote Similarity NPD6823 Phase 2
0.6784 Remote Similarity NPD4357 Discontinued
0.6784 Remote Similarity NPD7390 Discontinued
0.6776 Remote Similarity NPD7893 Clinical (unspecified phase)
0.6772 Remote Similarity NPD3972 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