Structure

Physi-Chem Properties

Molecular Weight:  412.12
Volume:  395.516
LogP:  3.595
LogD:  2.079
LogS:  -4.336
# Rotatable Bonds:  3
TPSA:  129.59
# H-Bond Aceptor:  8
# H-Bond Donor:  4
# Rings:  5
# Heavy Atoms:  8

MedChem Properties

QED Drug-Likeness Score:  0.483
Synthetic Accessibility Score:  4.288
Fsp3:  0.318
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:  -5.027
MDCK Permeability:  1.0552955245657358e-05
Pgp-inhibitor:  0.007
Pgp-substrate:  0.003
Human Intestinal Absorption (HIA):  0.039
20% Bioavailability (F20%):  0.005
30% Bioavailability (F30%):  0.028

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.022
Plasma Protein Binding (PPB):  90.90247344970703%
Volume Distribution (VD):  1.107
Pgp-substrate:  10.14815902709961%

ADMET: Metabolism

CYP1A2-inhibitor:  0.733
CYP1A2-substrate:  0.461
CYP2C19-inhibitor:  0.362
CYP2C19-substrate:  0.066
CYP2C9-inhibitor:  0.799
CYP2C9-substrate:  0.831
CYP2D6-inhibitor:  0.676
CYP2D6-substrate:  0.193
CYP3A4-inhibitor:  0.625
CYP3A4-substrate:  0.316

ADMET: Excretion

Clearance (CL):  2.164
Half-life (T1/2):  0.716

ADMET: Toxicity

hERG Blockers:  0.008
Human Hepatotoxicity (H-HT):  0.968
Drug-inuced Liver Injury (DILI):  0.958
AMES Toxicity:  0.966
Rat Oral Acute Toxicity:  0.912
Maximum Recommended Daily Dose:  0.802
Skin Sensitization:  0.288
Carcinogencity:  0.995
Eye Corrosion:  0.003
Eye Irritation:  0.169
Respiratory Toxicity:  0.459

Download Data

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

  Natural Product: NPC93215

Natural Product ID:  NPC93215
Common Name*:   Austocystin D
IUPAC Name:   n.a.
Synonyms:   Austocystin D
Standard InCHIKey:  VXTQFTUOAJRUDO-IFMALSPDSA-N
Standard InCHI:  InChI=1S/C22H20O8/c1-21(2,26)6-5-10-3-4-11(23)14-17(24)15-12(29-19(10)14)9-13-16(18(15)25)22(27)7-8-28-20(22)30-13/h3-4,7-9,20,23,25-27H,5-6H2,1-2H3/t20-,22-/m1/s1
SMILES:  Oc1ccc(c2c1c(=O)c1c(o2)cc2c(c1O)[C@]1(O)C=CO[C@@H]1O2)CCC(O)(C)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL1966436
PubChem CID:   5470400
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000002] Organoheterocyclic compounds
      • [CHEMONTID:0000123] Benzopyrans
        • [CHEMONTID:0003410] 1-benzopyrans
          • [CHEMONTID:0002817] Dibenzopyrans
            • [CHEMONTID:0000200] Xanthenes
              • [CHEMONTID:0000204] Xanthones
                • [CHEMONTID:0003518] 4-prenylated xanthones

*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
NPO27058 Aspergillus ustus Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[19769341]
NPO27058 Aspergillus ustus Species Aspergillaceae Eukaryota Suberites domuncula n.a. n.a. PMID[19778087]
NPO30161 Aspergillus Genus Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[21348461]
NPO27058 Aspergillus ustus Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[21348461]
NPO30161 Aspergillus Genus Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[21667925]
NPO30161 Aspergillus Genus Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[22026385]
NPO27058 Aspergillus ustus Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[24033077]
NPO27058 Aspergillus ustus Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[25706180]
NPO27058 Aspergillus ustus Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[29286660]
NPO27058 Aspergillus ustus Species Aspergillaceae 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
NPT367 Cell Line MDA-N Homo sapiens GI50 n.a. 10.0 nM PMID[508886]
NPT368 Cell Line SN12C Homo sapiens GI50 n.a. 8689.6 nM PMID[508886]
NPT369 Cell Line ACHN Homo sapiens GI50 n.a. 10.0 nM PMID[508886]
NPT370 Cell Line NCI-H23 Homo sapiens GI50 n.a. 10.0 nM PMID[508886]
NPT371 Cell Line UO-31 Homo sapiens GI50 n.a. 10.0 nM PMID[508886]
NPT372 Cell Line HOP-92 Homo sapiens GI50 n.a. 250.61 nM PMID[508886]
NPT90 Cell Line DU-145 Homo sapiens GI50 n.a. 10.0 nM PMID[508886]
NPT374 Cell Line SF-539 Homo sapiens GI50 n.a. 514.04 nM PMID[508886]
NPT373 Cell Line SK-MEL-5 Homo sapiens GI50 n.a. 10.19 nM PMID[508886]
NPT375 Cell Line Malme-3M Homo sapiens GI50 n.a. 1081.43 nM PMID[508886]
NPT111 Cell Line K562 Homo sapiens GI50 n.a. 20044.72 nM PMID[508886]
NPT376 Cell Line A498 Homo sapiens GI50 n.a. 10.0 nM PMID[508886]
NPT377 Cell Line OVCAR-3 Homo sapiens GI50 n.a. 10.0 nM PMID[508886]
NPT112 Cell Line MOLT-4 Homo sapiens GI50 n.a. 10.62 nM PMID[508886]
NPT379 Cell Line HOP-62 Homo sapiens GI50 n.a. 146.89 nM PMID[508886]
NPT378 Cell Line NCI/ADR-RES Homo sapiens GI50 n.a. 10.0 nM PMID[508886]
NPT380 Cell Line U-251 Homo sapiens GI50 n.a. 10.0 nM PMID[508886]
NPT381 Cell Line OVCAR-8 Homo sapiens GI50 n.a. 10.0 nM PMID[508886]
NPT382 Cell Line OVCAR-5 Homo sapiens GI50 n.a. 61.52 nM PMID[508886]
NPT82 Cell Line MDA-MB-231 Homo sapiens GI50 n.a. 2264.64 nM PMID[508886]
NPT383 Cell Line SNB-19 Homo sapiens GI50 n.a. 147.57 nM PMID[508886]
NPT385 Cell Line SR Homo sapiens GI50 n.a. 1227.44 nM PMID[508886]
NPT384 Cell Line TK-10 Homo sapiens GI50 n.a. 10.0 nM PMID[508886]
NPT323 Cell Line SW-620 Homo sapiens GI50 n.a. 10.0 nM PMID[508886]
NPT455 Cell Line NCI-H522 Homo sapiens GI50 n.a. 5272.3 nM PMID[508886]
NPT386 Cell Line KM12 Homo sapiens GI50 n.a. 10.0 nM PMID[508886]
NPT387 Cell Line M14 Homo sapiens GI50 n.a. 411.15 nM PMID[508886]
NPT388 Cell Line NCI-H322M Homo sapiens GI50 n.a. 10.0 nM PMID[508886]
NPT389 Cell Line RPMI-8226 Homo sapiens GI50 n.a. 475.34 nM PMID[508886]
NPT456 Cell Line OVCAR-4 Homo sapiens GI50 n.a. 10.0 nM PMID[508886]
NPT390 Cell Line LOX IMVI Homo sapiens GI50 n.a. 9311.08 nM PMID[508886]
NPT457 Cell Line BT-549 Homo sapiens GI50 n.a. 9057.33 nM PMID[508886]
NPT147 Cell Line SK-MEL-2 Homo sapiens GI50 n.a. 10.0 nM PMID[508886]
NPT391 Cell Line HCC 2998 Homo sapiens GI50 n.a. 10.0 nM PMID[508886]
NPT81 Cell Line A549 Homo sapiens GI50 n.a. 726.11 nM PMID[508886]
NPT392 Cell Line SNB-75 Homo sapiens GI50 n.a. 56.23 nM PMID[508886]
NPT148 Cell Line HCT-15 Homo sapiens GI50 n.a. 10.0 nM PMID[508886]
NPT393 Cell Line HCT-116 Homo sapiens GI50 n.a. 19.95 nM PMID[508886]
NPT395 Cell Line SF-268 Homo sapiens GI50 n.a. 55.98 nM PMID[508886]
NPT394 Cell Line EKVX Homo sapiens GI50 n.a. 254.68 nM PMID[508886]
NPT306 Cell Line PC-3 Homo sapiens GI50 n.a. 118.85 nM PMID[508886]
NPT83 Cell Line MCF7 Homo sapiens GI50 n.a. 10.0 nM PMID[508886]
NPT146 Cell Line SK-OV-3 Homo sapiens GI50 n.a. 12.53 nM PMID[508886]
NPT397 Cell Line NCI-H460 Homo sapiens GI50 n.a. 50.7 nM PMID[508886]
NPT308 Cell Line CAKI-1 Homo sapiens GI50 n.a. 10.0 nM PMID[508886]
NPT398 Cell Line UACC-62 Homo sapiens GI50 n.a. 10.0 nM PMID[508886]
NPT400 Cell Line MDA-MB-435 Homo sapiens GI50 n.a. 10.0 nM PMID[508886]
NPT399 Cell Line SF-295 Homo sapiens GI50 n.a. 8871.56 nM PMID[508886]
NPT458 Cell Line IGROV-1 Homo sapiens GI50 n.a. 10.0 nM PMID[508886]
NPT402 Cell Line Hs-578T Homo sapiens GI50 n.a. 10185.91 nM PMID[508886]
NPT401 Cell Line 786-0 Homo sapiens GI50 n.a. 7063.18 nM PMID[508886]
NPT403 Cell Line UACC-257 Homo sapiens GI50 n.a. 18.41 nM PMID[508886]
NPT404 Cell Line CCRF-CEM Homo sapiens GI50 n.a. 9794.9 nM PMID[508886]
NPT405 Cell Line NCI-H226 Homo sapiens GI50 n.a. 10.0 nM PMID[508886]
NPT139 Cell Line HT-29 Homo sapiens GI50 n.a. 1235.95 nM PMID[508886]
NPT170 Cell Line SK-MEL-28 Homo sapiens GI50 n.a. 285.76 nM PMID[508886]
NPT406 Cell Line RXF 393 Homo sapiens GI50 n.a. 147.91 nM PMID[508886]
NPT407 Cell Line COLO 205 Homo sapiens GI50 n.a. 10.91 nM PMID[508886]
NPT148 Cell Line HCT-15 Homo sapiens RatioGI50 > 1000.0 n.a. PMID[508887]
NPT83 Cell Line MCF7 Homo sapiens RatioGI50 > 1000.0 n.a. PMID[508887]
NPT83 Cell Line MCF7 Homo sapiens RatioGI50 > 10000.0 n.a. PMID[508887]
NPT148 Cell Line HCT-15 Homo sapiens GI50 = 42.0 nM PMID[508887]
NPT323 Cell Line SW-620 Homo sapiens GI50 = 27.0 nM PMID[508887]
NPT306 Cell Line PC-3 Homo sapiens GI50 = 3.0 nM PMID[508887]
NPT82 Cell Line MDA-MB-231 Homo sapiens GI50 = 549.0 nM PMID[508887]
NPT83 Cell Line MCF7 Homo sapiens GI50 < 1.0 nM PMID[508887]
NPT385 Cell Line SR Homo sapiens GI50 = 16.0 nM PMID[508887]
NPT165 Cell Line HeLa Homo sapiens GI50 > 5000.0 nM PMID[508887]
NPT81 Cell Line A549 Homo sapiens GI50 > 5000.0 nM PMID[508887]
NPT2257 Cell Line MCF-10A Homo sapiens GI50 = 3513.0 nM PMID[508887]
NPT737 Cell Line HUVEC Homo sapiens GI50 = 4249.0 nM PMID[508887]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. GI50 = 3358.0 nM PMID[508887]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. GI50 > 10000.0 nM PMID[508887]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. GI50 = 4946.0 nM PMID[508887]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. AbsAC35_uM = 0.065 uM PMID[508888]
NPT2 Others Unspecified AbsAC35_uM < 0.026 uM PMID[508888]
NPT2 Others Unspecified AbsAC35_uM = 0.0326 uM PMID[508888]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. AbsAC35_uM = 0.0808 uM PMID[508888]

☑ 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 NPC93215 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
0.9545 High Similarity NPC211482
0.9545 High Similarity NPC476652
0.943 High Similarity NPC471286
0.9423 High Similarity NPC470607
0.9359 High Similarity NPC470606
0.9359 High Similarity NPC23817
0.9308 High Similarity NPC183672
0.9308 High Similarity NPC91288
0.9295 High Similarity NPC265480
0.9295 High Similarity NPC149368
0.9295 High Similarity NPC17521
0.929 High Similarity NPC106625
0.9286 High Similarity NPC472636
0.9286 High Similarity NPC318424
0.9245 High Similarity NPC131745
0.9245 High Similarity NPC259834
0.9245 High Similarity NPC44947
0.9245 High Similarity NPC310603
0.9241 High Similarity NPC200708
0.9241 High Similarity NPC472320
0.9236 High Similarity NPC122809
0.9236 High Similarity NPC161650
0.9231 High Similarity NPC470604
0.9231 High Similarity NPC470603
0.9231 High Similarity NPC470605
0.9231 High Similarity NPC99233
0.9226 High Similarity NPC473996
0.9226 High Similarity NPC259182
0.9226 High Similarity NPC121001
0.9187 High Similarity NPC66087
0.9187 High Similarity NPC179198
0.9187 High Similarity NPC124155
0.9187 High Similarity NPC257566
0.9187 High Similarity NPC278419
0.9182 High Similarity NPC47923
0.9177 High Similarity NPC308265
0.9177 High Similarity NPC50430
0.9177 High Similarity NPC311574
0.9177 High Similarity NPC73511
0.9177 High Similarity NPC264932
0.9172 High Similarity NPC206378
0.9172 High Similarity NPC127406
0.9167 High Similarity NPC268950
0.9167 High Similarity NPC108706
0.9167 High Similarity NPC211158
0.9167 High Similarity NPC78021
0.9167 High Similarity NPC87304
0.9161 High Similarity NPC471675
0.9161 High Similarity NPC472580
0.9125 High Similarity NPC150164
0.9125 High Similarity NPC190450
0.9119 High Similarity NPC306978
0.9119 High Similarity NPC172687
0.9119 High Similarity NPC271479
0.9114 High Similarity NPC156457
0.9114 High Similarity NPC313163
0.9114 High Similarity NPC210048
0.9114 High Similarity NPC258035
0.9114 High Similarity NPC161749
0.9114 High Similarity NPC197896
0.9114 High Similarity NPC6985
0.9114 High Similarity NPC43638
0.9108 High Similarity NPC95090
0.9108 High Similarity NPC26195
0.9108 High Similarity NPC169248
0.9108 High Similarity NPC27408
0.9108 High Similarity NPC97052
0.9108 High Similarity NPC72649
0.9108 High Similarity NPC39351
0.9103 High Similarity NPC476238
0.9103 High Similarity NPC327269
0.9103 High Similarity NPC31627
0.9103 High Similarity NPC88484
0.9103 High Similarity NPC259767
0.9103 High Similarity NPC210597
0.9103 High Similarity NPC477957
0.9097 High Similarity NPC472421
0.908 High Similarity NPC473202
0.9074 High Similarity NPC178851
0.9062 High Similarity NPC303913
0.9062 High Similarity NPC92589
0.9051 High Similarity NPC170475
0.9051 High Similarity NPC45165
0.9045 High Similarity NPC39360
0.9045 High Similarity NPC83283
0.9045 High Similarity NPC209760
0.9045 High Similarity NPC121910
0.9045 High Similarity NPC143851
0.9045 High Similarity NPC100134
0.9045 High Similarity NPC29763
0.9045 High Similarity NPC168805
0.9045 High Similarity NPC210003
0.9038 High Similarity NPC472420
0.9038 High Similarity NPC474772
0.9038 High Similarity NPC472422
0.9038 High Similarity NPC190217
0.9038 High Similarity NPC471677
0.9038 High Similarity NPC244577
0.9038 High Similarity NPC472423
0.9038 High Similarity NPC23253
0.9038 High Similarity NPC474744
0.9038 High Similarity NPC263384
0.9038 High Similarity NPC471676
0.9036 High Similarity NPC475233
0.903 High Similarity NPC98776
0.9024 High Similarity NPC8704
0.9024 High Similarity NPC212748
0.9024 High Similarity NPC287884
0.9012 High Similarity NPC72016
0.9006 High Similarity NPC127782
0.9006 High Similarity NPC300537
0.9006 High Similarity NPC125991
0.9 High Similarity NPC153342
0.9 High Similarity NPC19554
0.9 High Similarity NPC271270
0.9 High Similarity NPC74749
0.9 High Similarity NPC142860
0.9 High Similarity NPC43971
0.9 High Similarity NPC246469
0.9 High Similarity NPC97285
0.8994 High Similarity NPC288084
0.8994 High Similarity NPC60966
0.8994 High Similarity NPC44931
0.8994 High Similarity NPC182634
0.8994 High Similarity NPC65003
0.8994 High Similarity NPC473512
0.8994 High Similarity NPC108831
0.8994 High Similarity NPC129827
0.8987 High Similarity NPC92395
0.8987 High Similarity NPC476169
0.8987 High Similarity NPC471116
0.8987 High Similarity NPC87404
0.8987 High Similarity NPC108937
0.8987 High Similarity NPC279218
0.8981 High Similarity NPC150123
0.8981 High Similarity NPC56232
0.8981 High Similarity NPC244583
0.8981 High Similarity NPC10807
0.8981 High Similarity NPC161881
0.8981 High Similarity NPC475790
0.8981 High Similarity NPC285623
0.8976 High Similarity NPC108202
0.8974 High Similarity NPC477240
0.8974 High Similarity NPC38775
0.8974 High Similarity NPC191154
0.8974 High Similarity NPC106025
0.8974 High Similarity NPC214454
0.897 High Similarity NPC475825
0.897 High Similarity NPC235575
0.897 High Similarity NPC223375
0.897 High Similarity NPC261254
0.8968 High Similarity NPC199335
0.8963 High Similarity NPC259905
0.8963 High Similarity NPC5319
0.8944 High Similarity NPC94155
0.8938 High Similarity NPC472459
0.8938 High Similarity NPC320283
0.8938 High Similarity NPC138811
0.8938 High Similarity NPC111929
0.8938 High Similarity NPC43761
0.8938 High Similarity NPC473634
0.8938 High Similarity NPC41121
0.8938 High Similarity NPC22062
0.8931 High Similarity NPC129053
0.8931 High Similarity NPC323593
0.8931 High Similarity NPC215917
0.8931 High Similarity NPC261866
0.8931 High Similarity NPC10754
0.8931 High Similarity NPC20530
0.8931 High Similarity NPC475797
0.8931 High Similarity NPC203500
0.8931 High Similarity NPC469936
0.8931 High Similarity NPC78554
0.8931 High Similarity NPC321372
0.8931 High Similarity NPC109967
0.8931 High Similarity NPC474609
0.8931 High Similarity NPC307938
0.8931 High Similarity NPC474738
0.8924 High Similarity NPC7989
0.8924 High Similarity NPC223701
0.8924 High Similarity NPC472583
0.8917 High Similarity NPC474023
0.8917 High Similarity NPC254412
0.8917 High Similarity NPC278476
0.8917 High Similarity NPC471291
0.8917 High Similarity NPC262039
0.8917 High Similarity NPC134819
0.8917 High Similarity NPC328740
0.8917 High Similarity NPC209846
0.8917 High Similarity NPC477897
0.8917 High Similarity NPC471229
0.8917 High Similarity NPC289774
0.8917 High Similarity NPC262038
0.8917 High Similarity NPC319910
0.8917 High Similarity NPC474021
0.891 High Similarity NPC89442
0.891 High Similarity NPC277032
0.891 High Similarity NPC472628
0.891 High Similarity NPC88886
0.891 High Similarity NPC104172

  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 NPC93215 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
0.9114 High Similarity NPD4381 Clinical (unspecified phase)
0.8963 High Similarity NPD7804 Clinical (unspecified phase)
0.8802 High Similarity NPD6559 Discontinued
0.8788 High Similarity NPD3818 Discontinued
0.8758 High Similarity NPD7075 Discontinued
0.8734 High Similarity NPD4380 Phase 2
0.8688 High Similarity NPD2393 Clinical (unspecified phase)
0.8683 High Similarity NPD7074 Phase 3
0.8654 High Similarity NPD4378 Clinical (unspecified phase)
0.8623 High Similarity NPD7054 Approved
0.8571 High Similarity NPD7472 Approved
0.8571 High Similarity NPD7096 Clinical (unspecified phase)
0.8521 High Similarity NPD6797 Phase 2
0.8519 High Similarity NPD8443 Clinical (unspecified phase)
0.8509 High Similarity NPD1934 Approved
0.8471 Intermediate Similarity NPD7251 Discontinued
0.8457 Intermediate Similarity NPD7819 Suspended
0.8447 Intermediate Similarity NPD7411 Suspended
0.8442 Intermediate Similarity NPD1550 Clinical (unspecified phase)
0.8442 Intermediate Similarity NPD1552 Clinical (unspecified phase)
0.8421 Intermediate Similarity NPD7808 Phase 3
0.8418 Intermediate Similarity NPD7410 Clinical (unspecified phase)
0.8395 Intermediate Similarity NPD6801 Discontinued
0.8387 Intermediate Similarity NPD1549 Phase 2
0.8314 Intermediate Similarity NPD4338 Clinical (unspecified phase)
0.8242 Intermediate Similarity NPD3882 Suspended
0.8239 Intermediate Similarity NPD6799 Approved
0.8232 Intermediate Similarity NPD2801 Approved
0.8225 Intermediate Similarity NPD6168 Clinical (unspecified phase)
0.8225 Intermediate Similarity NPD6166 Phase 2
0.8225 Intermediate Similarity NPD6167 Clinical (unspecified phase)
0.8225 Intermediate Similarity NPD7852 Clinical (unspecified phase)
0.8204 Intermediate Similarity NPD5494 Approved
0.8194 Intermediate Similarity NPD1510 Phase 2
0.8182 Intermediate Similarity NPD3817 Phase 2
0.816 Intermediate Similarity NPD6599 Discontinued
0.8155 Intermediate Similarity NPD6959 Discontinued
0.8141 Intermediate Similarity NPD2796 Approved
0.8125 Intermediate Similarity NPD1511 Approved
0.8101 Intermediate Similarity NPD2800 Approved
0.8084 Intermediate Similarity NPD3749 Approved
0.8052 Intermediate Similarity NPD1240 Approved
0.8045 Intermediate Similarity NPD7879 Clinical (unspecified phase)
0.8025 Intermediate Similarity NPD1512 Approved
0.8024 Intermediate Similarity NPD7768 Phase 2
0.8024 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.8 Intermediate Similarity NPD6232 Discontinued
0.7965 Intermediate Similarity NPD7473 Discontinued
0.7963 Intermediate Similarity NPD2533 Approved
0.7963 Intermediate Similarity NPD2532 Approved
0.7963 Intermediate Similarity NPD2534 Approved
0.7949 Intermediate Similarity NPD1607 Approved
0.7941 Intermediate Similarity NPD7199 Phase 2
0.7875 Intermediate Similarity NPD7421 Clinical (unspecified phase)
0.7872 Intermediate Similarity NPD7584 Approved
0.7866 Intermediate Similarity NPD5403 Approved
0.7866 Intermediate Similarity NPD920 Approved
0.7866 Intermediate Similarity NPD6980 Clinical (unspecified phase)
0.7853 Intermediate Similarity NPD8312 Approved
0.7853 Intermediate Similarity NPD8313 Approved
0.7849 Intermediate Similarity NPD7184 Clinical (unspecified phase)
0.7826 Intermediate Similarity NPD3750 Approved
0.7824 Intermediate Similarity NPD6234 Discontinued
0.7798 Intermediate Similarity NPD8455 Phase 2
0.7797 Intermediate Similarity NPD4419 Clinical (unspecified phase)
0.7791 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.7771 Intermediate Similarity NPD5844 Phase 1
0.7764 Intermediate Similarity NPD1243 Approved
0.7751 Intermediate Similarity NPD5402 Approved
0.7744 Intermediate Similarity NPD642 Clinical (unspecified phase)
0.7744 Intermediate Similarity NPD5401 Approved
0.7742 Intermediate Similarity NPD6780 Approved
0.7742 Intermediate Similarity NPD6782 Approved
0.7742 Intermediate Similarity NPD6776 Approved
0.7742 Intermediate Similarity NPD6778 Approved
0.7742 Intermediate Similarity NPD6777 Approved
0.7742 Intermediate Similarity NPD6781 Approved
0.7742 Intermediate Similarity NPD6779 Approved
0.773 Intermediate Similarity NPD643 Clinical (unspecified phase)
0.7716 Intermediate Similarity NPD1878 Clinical (unspecified phase)
0.7716 Intermediate Similarity NPD4628 Phase 3
0.7714 Intermediate Similarity NPD7228 Approved
0.7706 Intermediate Similarity NPD4967 Phase 2
0.7706 Intermediate Similarity NPD4965 Approved
0.7706 Intermediate Similarity NPD4966 Approved
0.7702 Intermediate Similarity NPD970 Clinical (unspecified phase)
0.7692 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.7688 Intermediate Similarity NPD2935 Discontinued
0.7688 Intermediate Similarity NPD1551 Phase 2
0.7684 Intermediate Similarity NPD5953 Discontinued
0.7667 Intermediate Similarity NPD8055 Clinical (unspecified phase)
0.7665 Intermediate Similarity NPD7458 Discontinued
0.764 Intermediate Similarity NPD2344 Approved
0.7633 Intermediate Similarity NPD37 Approved
0.7625 Intermediate Similarity NPD2799 Discontinued
0.7619 Intermediate Similarity NPD7435 Discontinued
0.7616 Intermediate Similarity NPD919 Approved
0.7614 Intermediate Similarity NPD3751 Discontinued
0.761 Intermediate Similarity NPD6651 Approved
0.7588 Intermediate Similarity NPD1465 Phase 2
0.7586 Intermediate Similarity NPD3787 Discontinued
0.7584 Intermediate Similarity NPD7993 Clinical (unspecified phase)
0.758 Intermediate Similarity NPD4907 Clinical (unspecified phase)
0.7571 Intermediate Similarity NPD7286 Phase 2
0.756 Intermediate Similarity NPD3226 Approved
0.7543 Intermediate Similarity NPD3926 Phase 2
0.7529 Intermediate Similarity NPD1247 Approved
0.7526 Intermediate Similarity NPD7696 Phase 3
0.7526 Intermediate Similarity NPD7783 Phase 2
0.7526 Intermediate Similarity NPD7697 Approved
0.7526 Intermediate Similarity NPD7698 Approved
0.7526 Intermediate Similarity NPD7782 Clinical (unspecified phase)
0.7516 Intermediate Similarity NPD3748 Approved
0.7513 Intermediate Similarity NPD8151 Discontinued
0.7487 Intermediate Similarity NPD7870 Phase 2
0.7487 Intermediate Similarity NPD7871 Phase 2
0.7486 Intermediate Similarity NPD5711 Approved
0.7486 Intermediate Similarity NPD5710 Approved
0.7474 Intermediate Similarity NPD6823 Phase 2
0.7473 Intermediate Similarity NPD6535 Approved
0.7473 Intermediate Similarity NPD6534 Approved
0.7469 Intermediate Similarity NPD6099 Approved
0.7469 Intermediate Similarity NPD6100 Approved
0.7468 Intermediate Similarity NPD2313 Discontinued
0.7461 Intermediate Similarity NPD7701 Phase 2
0.7461 Intermediate Similarity NPD7585 Approved
0.7455 Intermediate Similarity NPD2309 Approved
0.7452 Intermediate Similarity NPD4908 Phase 1
0.7446 Intermediate Similarity NPD8397 Clinical (unspecified phase)
0.7444 Intermediate Similarity NPD7685 Pre-registration
0.7438 Intermediate Similarity NPD1933 Approved
0.7436 Intermediate Similarity NPD2798 Approved
0.7432 Intermediate Similarity NPD8434 Phase 2
0.7423 Intermediate Similarity NPD2346 Discontinued
0.7411 Intermediate Similarity NPD7930 Approved
0.7409 Intermediate Similarity NPD7583 Approved
0.7407 Intermediate Similarity NPD7033 Discontinued
0.7396 Intermediate Similarity NPD1653 Approved
0.7394 Intermediate Similarity NPD8090 Clinical (unspecified phase)
0.7394 Intermediate Similarity NPD6398 Clinical (unspecified phase)
0.7385 Intermediate Similarity NPD7875 Clinical (unspecified phase)
0.7385 Intermediate Similarity NPD7874 Approved
0.738 Intermediate Similarity NPD4363 Phase 3
0.738 Intermediate Similarity NPD4360 Phase 2
0.7365 Intermediate Similarity NPD7390 Discontinued
0.7354 Intermediate Similarity NPD7699 Phase 2
0.7354 Intermediate Similarity NPD7700 Phase 2
0.7348 Intermediate Similarity NPD7240 Approved
0.7347 Intermediate Similarity NPD7801 Approved
0.7342 Intermediate Similarity NPD6832 Phase 2
0.734 Intermediate Similarity NPD4362 Clinical (unspecified phase)
0.734 Intermediate Similarity NPD4361 Phase 2
0.7338 Intermediate Similarity NPD1610 Phase 2
0.7301 Intermediate Similarity NPD1509 Clinical (unspecified phase)
0.7288 Intermediate Similarity NPD7229 Phase 3
0.7277 Intermediate Similarity NPD7501 Clinical (unspecified phase)
0.7273 Intermediate Similarity NPD2424 Discontinued
0.7267 Intermediate Similarity NPD1613 Approved
0.7267 Intermediate Similarity NPD943 Approved
0.7267 Intermediate Similarity NPD7615 Clinical (unspecified phase)
0.7267 Intermediate Similarity NPD1612 Clinical (unspecified phase)
0.7261 Intermediate Similarity NPD1203 Approved
0.725 Intermediate Similarity NPD3268 Approved
0.7233 Intermediate Similarity NPD1529 Clinical (unspecified phase)
0.7226 Intermediate Similarity NPD1547 Clinical (unspecified phase)
0.7226 Intermediate Similarity NPD1091 Approved
0.7222 Intermediate Similarity NPD5123 Clinical (unspecified phase)
0.7222 Intermediate Similarity NPD5124 Phase 1
0.7222 Intermediate Similarity NPD6355 Discontinued
0.7219 Intermediate Similarity NPD7004 Clinical (unspecified phase)
0.7216 Intermediate Similarity NPD8320 Phase 1
0.7216 Intermediate Similarity NPD8319 Approved
0.7212 Intermediate Similarity NPD2343 Clinical (unspecified phase)
0.7207 Intermediate Similarity NPD2403 Approved
0.7202 Intermediate Similarity NPD5058 Phase 3
0.7188 Intermediate Similarity NPD4625 Phase 3
0.717 Intermediate Similarity NPD1530 Clinical (unspecified phase)
0.7166 Intermediate Similarity NPD4287 Approved
0.7152 Intermediate Similarity NPD2797 Approved
0.7151 Intermediate Similarity NPD8150 Discontinued
0.7143 Intermediate Similarity NPD1729 Discontinued
0.7143 Intermediate Similarity NPD6212 Phase 3
0.7143 Intermediate Similarity NPD3764 Approved
0.7143 Intermediate Similarity NPD6214 Clinical (unspecified phase)
0.7143 Intermediate Similarity NPD6213 Phase 3
0.7143 Intermediate Similarity NPD6798 Discontinued
0.7126 Intermediate Similarity NPD2654 Approved
0.7117 Intermediate Similarity NPD230 Phase 1
0.7108 Intermediate Similarity NPD6004 Phase 3
0.7108 Intermediate Similarity NPD6005 Phase 3
0.7108 Intermediate Similarity NPD6003 Clinical (unspecified phase)
0.7108 Intermediate Similarity NPD6006 Clinical (unspecified phase)
0.7108 Intermediate Similarity NPD6002 Phase 3
0.7091 Intermediate Similarity NPD4308 Phase 3
0.7086 Intermediate Similarity NPD5761 Phase 2
0.7086 Intermediate Similarity NPD5760 Phase 2
0.7078 Intermediate Similarity NPD1548 Phase 1
0.707 Intermediate Similarity NPD9717 Approved
0.7055 Intermediate Similarity NPD4060 Phase 1
0.7052 Intermediate Similarity NPD5808 Clinical (unspecified phase)

  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