Structure

Physi-Chem Properties

Molecular Weight:  538.16
Volume:  555.941
LogP:  5.861
LogD:  3.623
LogS:  -5.493
# Rotatable Bonds:  10
TPSA:  122.52
# H-Bond Aceptor:  8
# H-Bond Donor:  3
# Rings:  4
# Heavy Atoms:  8

MedChem Properties

QED Drug-Likeness Score:  0.156
Synthetic Accessibility Score:  2.622
Fsp3:  0.062
Lipinski Rule-of-5:  Rejected
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  0
Golden Triangle Rule:  Rejected
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -5.225
MDCK Permeability:  1.2496843737608287e-05
Pgp-inhibitor:  0.116
Pgp-substrate:  0.008
Human Intestinal Absorption (HIA):  0.032
20% Bioavailability (F20%):  0.007
30% Bioavailability (F30%):  0.173

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.046
Plasma Protein Binding (PPB):  108.3249740600586%
Volume Distribution (VD):  0.163
Pgp-substrate:  0.31481778621673584%

ADMET: Metabolism

CYP1A2-inhibitor:  0.611
CYP1A2-substrate:  0.152
CYP2C19-inhibitor:  0.882
CYP2C19-substrate:  0.05
CYP2C9-inhibitor:  0.873
CYP2C9-substrate:  0.978
CYP2D6-inhibitor:  0.026
CYP2D6-substrate:  0.919
CYP3A4-inhibitor:  0.714
CYP3A4-substrate:  0.352

ADMET: Excretion

Clearance (CL):  7.421
Half-life (T1/2):  0.461

ADMET: Toxicity

hERG Blockers:  0.126
Human Hepatotoxicity (H-HT):  0.071
Drug-inuced Liver Injury (DILI):  0.914
AMES Toxicity:  0.88
Rat Oral Acute Toxicity:  0.186
Maximum Recommended Daily Dose:  0.909
Skin Sensitization:  0.953
Carcinogencity:  0.793
Eye Corrosion:  0.003
Eye Irritation:  0.926
Respiratory Toxicity:  0.189

Download Data

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

  Natural Product: NPC188967

Natural Product ID:  NPC188967
Common Name*:   Rhuschalcone I
IUPAC Name:   (E)-3-[4-[4-hydroxy-5-[(E)-3-(4-hydroxyphenyl)prop-2-enoyl]-2-methoxyphenoxy]phenyl]-1-(2-hydroxy-4-methoxyphenyl)prop-2-en-1-one
Synonyms:  
Standard InCHIKey:  KGGDBGGPDRWGEC-BGPOSVGRSA-N
Standard InCHI:  InChI=1S/C32H26O8/c1-38-24-13-14-25(29(36)17-24)27(34)15-7-21-5-11-23(12-6-21)40-32-18-26(30(37)19-31(32)39-2)28(35)16-8-20-3-9-22(33)10-4-20/h3-19,33,36-37H,1-2H3/b15-7+,16-8+
SMILES:  COc1ccc(C(=O)/C=C/c2ccc(cc2)Oc2cc(C(=O)/C=C/c3ccc(cc3)O)c(cc2OC)O)c(c1)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL467415
PubChem CID:   5472697
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000261] Phenylpropanoids and polyketides
      • [CHEMONTID:0003467] Linear 1,3-diarylpropanoids
        • [CHEMONTID:0001630] Chalcones and dihydrochalcones
          • [CHEMONTID:0003472] 2'-Hydroxychalcones

*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
NPO32638 rhus pyroides Species Anacardiaceae Eukaryota root bark n.a. n.a. PMID[12762790]

☑ 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
NPT407 Cell Line COLO 205 Homo sapiens ED50 = 11.0 ug ml-1 PMID[475682]
NPT393 Cell Line HCT-116 Homo sapiens ED50 = 5.0 ug ml-1 PMID[475682]
NPT148 Cell Line HCT-15 Homo sapiens ED50 = 51.0 ug ml-1 PMID[475682]
NPT139 Cell Line HT-29 Homo sapiens ED50 = 3.0 ug ml-1 PMID[475682]
NPT386 Cell Line KM12 Homo sapiens ED50 = 17.0 ug ml-1 PMID[475682]
NPT323 Cell Line SW-620 Homo sapiens ED50 = 42.0 ug ml-1 PMID[475682]
NPT368 Cell Line SN12C Homo sapiens GI50 n.a. 3741.11 nM PMID[475683]
NPT367 Cell Line MDA-N Homo sapiens GI50 n.a. 3475.36 nM PMID[475683]
NPT369 Cell Line ACHN Homo sapiens GI50 n.a. 2897.34 nM PMID[475683]
NPT370 Cell Line NCI-H23 Homo sapiens GI50 n.a. 2722.7 nM PMID[475683]
NPT371 Cell Line UO-31 Homo sapiens GI50 n.a. 3589.22 nM PMID[475683]
NPT116 Cell Line HL-60 Homo sapiens GI50 n.a. 3083.19 nM PMID[475683]
NPT372 Cell Line HOP-92 Homo sapiens GI50 n.a. 13867.56 nM PMID[475683]
NPT374 Cell Line SF-539 Homo sapiens GI50 n.a. 2187.76 nM PMID[475683]
NPT90 Cell Line DU-145 Homo sapiens GI50 n.a. 5956.62 nM PMID[475683]
NPT373 Cell Line SK-MEL-5 Homo sapiens GI50 n.a. 4017.91 nM PMID[475683]
NPT375 Cell Line Malme-3M Homo sapiens GI50 n.a. 17218.69 nM PMID[475683]
NPT376 Cell Line A498 Homo sapiens GI50 n.a. 1667.25 nM PMID[475683]
NPT111 Cell Line K562 Homo sapiens GI50 n.a. 3655.95 nM PMID[475683]
NPT112 Cell Line MOLT-4 Homo sapiens GI50 n.a. 2517.68 nM PMID[475683]
NPT377 Cell Line OVCAR-3 Homo sapiens GI50 n.a. 4295.36 nM PMID[475683]
NPT378 Cell Line NCI/ADR-RES Homo sapiens GI50 n.a. 3235.94 nM PMID[475683]
NPT379 Cell Line HOP-62 Homo sapiens GI50 n.a. 4830.59 nM PMID[475683]
NPT380 Cell Line U-251 Homo sapiens GI50 n.a. 3793.15 nM PMID[475683]
NPT381 Cell Line OVCAR-8 Homo sapiens GI50 n.a. 3451.44 nM PMID[475683]
NPT382 Cell Line OVCAR-5 Homo sapiens GI50 n.a. 4187.94 nM PMID[475683]
NPT82 Cell Line MDA-MB-231 Homo sapiens GI50 n.a. 3630.78 nM PMID[475683]
NPT383 Cell Line SNB-19 Homo sapiens GI50 n.a. 8298.51 nM PMID[475683]
NPT385 Cell Line SR Homo sapiens GI50 n.a. 1918.67 nM PMID[475683]
NPT384 Cell Line TK-10 Homo sapiens GI50 n.a. 4055.09 nM PMID[475683]
NPT323 Cell Line SW-620 Homo sapiens GI50 n.a. 4720.63 nM PMID[475683]
NPT455 Cell Line NCI-H522 Homo sapiens GI50 n.a. 2805.43 nM PMID[475683]
NPT386 Cell Line KM12 Homo sapiens GI50 n.a. 2648.5 nM PMID[475683]
NPT387 Cell Line M14 Homo sapiens GI50 n.a. 4742.42 nM PMID[475683]
NPT388 Cell Line NCI-H322M Homo sapiens GI50 n.a. 56623.93 nM PMID[475683]
NPT389 Cell Line RPMI-8226 Homo sapiens GI50 n.a. 1853.53 nM PMID[475683]
NPT456 Cell Line OVCAR-4 Homo sapiens GI50 n.a. 3228.49 nM PMID[475683]
NPT390 Cell Line LOX IMVI Homo sapiens GI50 n.a. 2269.86 nM PMID[475683]
NPT457 Cell Line BT-549 Homo sapiens GI50 n.a. 10375.28 nM PMID[475683]
NPT147 Cell Line SK-MEL-2 Homo sapiens GI50 n.a. 8570.38 nM PMID[475683]
NPT81 Cell Line A549 Homo sapiens GI50 n.a. 8709.64 nM PMID[475683]
NPT392 Cell Line SNB-75 Homo sapiens GI50 n.a. 5272.3 nM PMID[475683]
NPT393 Cell Line HCT-116 Homo sapiens GI50 n.a. 1866.38 nM PMID[475683]
NPT148 Cell Line HCT-15 Homo sapiens GI50 n.a. 2432.2 nM PMID[475683]
NPT395 Cell Line SF-268 Homo sapiens GI50 n.a. 5188.0 nM PMID[475683]
NPT394 Cell Line EKVX Homo sapiens GI50 n.a. 4008.67 nM PMID[475683]
NPT306 Cell Line PC-3 Homo sapiens GI50 n.a. 4841.72 nM PMID[475683]
NPT83 Cell Line MCF7 Homo sapiens GI50 n.a. 4405.55 nM PMID[475683]
NPT146 Cell Line SK-OV-3 Homo sapiens GI50 n.a. 9862.79 nM PMID[475683]
NPT397 Cell Line NCI-H460 Homo sapiens GI50 n.a. 4325.14 nM PMID[475683]
NPT396 Cell Line T47D Homo sapiens GI50 n.a. 4988.84 nM PMID[475683]
NPT398 Cell Line UACC-62 Homo sapiens GI50 n.a. 3265.88 nM PMID[475683]
NPT400 Cell Line MDA-MB-435 Homo sapiens GI50 n.a. 3548.13 nM PMID[475683]
NPT308 Cell Line CAKI-1 Homo sapiens GI50 n.a. 4102.04 nM PMID[475683]
NPT458 Cell Line IGROV-1 Homo sapiens GI50 n.a. 2594.18 nM PMID[475683]
NPT399 Cell Line SF-295 Homo sapiens GI50 n.a. 6412.1 nM PMID[475683]
NPT402 Cell Line Hs-578T Homo sapiens GI50 n.a. 16749.43 nM PMID[475683]
NPT401 Cell Line 786-0 Homo sapiens GI50 n.a. 2506.11 nM PMID[475683]
NPT403 Cell Line UACC-257 Homo sapiens GI50 n.a. 25527.01 nM PMID[475683]
NPT404 Cell Line CCRF-CEM Homo sapiens GI50 n.a. 2269.86 nM PMID[475683]
NPT139 Cell Line HT-29 Homo sapiens GI50 n.a. 2233.57 nM PMID[475683]
NPT170 Cell Line SK-MEL-28 Homo sapiens GI50 n.a. 2735.27 nM PMID[475683]
NPT407 Cell Line COLO 205 Homo sapiens GI50 n.a. 4335.11 nM PMID[475683]
NPT406 Cell Line RXF 393 Homo sapiens GI50 n.a. 2564.48 nM PMID[475683]

☑ 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 NPC188967 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
0.9934 High Similarity NPC190487
0.9934 High Similarity NPC154304
0.9608 High Similarity NPC185526
0.9551 High Similarity NPC272064
0.9481 High Similarity NPC183
0.9423 High Similarity NPC196179
0.9423 High Similarity NPC34089
0.9412 High Similarity NPC472915
0.9408 High Similarity NPC308451
0.9408 High Similarity NPC226973
0.9408 High Similarity NPC208043
0.9351 High Similarity NPC20830
0.9351 High Similarity NPC183597
0.9351 High Similarity NPC167815
0.9351 High Similarity NPC256612
0.9351 High Similarity NPC163780
0.9351 High Similarity NPC227325
0.9351 High Similarity NPC50715
0.9351 High Similarity NPC128863
0.9351 High Similarity NPC2476
0.9351 High Similarity NPC146165
0.9351 High Similarity NPC201136
0.9351 High Similarity NPC208197
0.9351 High Similarity NPC4455
0.9351 High Similarity NPC196439
0.9351 High Similarity NPC138360
0.9351 High Similarity NPC280339
0.9351 High Similarity NPC92659
0.9342 High Similarity NPC306821
0.9317 High Similarity NPC174700
0.929 High Similarity NPC472916
0.929 High Similarity NPC178854
0.9286 High Similarity NPC255350
0.9286 High Similarity NPC86485
0.9286 High Similarity NPC176775
0.9286 High Similarity NPC250822
0.9286 High Similarity NPC75279
0.9286 High Similarity NPC160951
0.9286 High Similarity NPC47781
0.9286 High Similarity NPC69394
0.9286 High Similarity NPC274327
0.9286 High Similarity NPC145379
0.9286 High Similarity NPC280937
0.9286 High Similarity NPC22519
0.9286 High Similarity NPC231018
0.9286 High Similarity NPC276409
0.9286 High Similarity NPC183878
0.9281 High Similarity NPC117579
0.9281 High Similarity NPC149614
0.9276 High Similarity NPC328119
0.9272 High Similarity NPC93034
0.9272 High Similarity NPC119660
0.925 High Similarity NPC243877
0.925 High Similarity NPC14662
0.9245 High Similarity NPC477840
0.9231 High Similarity NPC112954
0.9231 High Similarity NPC476981
0.9231 High Similarity NPC227192
0.9231 High Similarity NPC75215
0.9231 High Similarity NPC189179
0.9231 High Similarity NPC63454
0.9231 High Similarity NPC183851
0.9231 High Similarity NPC181960
0.9231 High Similarity NPC224137
0.9231 High Similarity NPC93376
0.9226 High Similarity NPC213622
0.9226 High Similarity NPC37392
0.9226 High Similarity NPC2928
0.9226 High Similarity NPC32557
0.9226 High Similarity NPC189960
0.9226 High Similarity NPC472909
0.9221 High Similarity NPC131624
0.9221 High Similarity NPC187498
0.9221 High Similarity NPC222830
0.9221 High Similarity NPC241498
0.9221 High Similarity NPC198826
0.9221 High Similarity NPC120163
0.9221 High Similarity NPC142540
0.9221 High Similarity NPC212678
0.9221 High Similarity NPC60972
0.9221 High Similarity NPC134677
0.9221 High Similarity NPC83508
0.9221 High Similarity NPC100887
0.9221 High Similarity NPC301323
0.9221 High Similarity NPC25270
0.9221 High Similarity NPC71334
0.9221 High Similarity NPC156222
0.9221 High Similarity NPC301123
0.9221 High Similarity NPC275836
0.9221 High Similarity NPC239128
0.9221 High Similarity NPC256283
0.9221 High Similarity NPC57030
0.9221 High Similarity NPC162313
0.9221 High Similarity NPC39732
0.9221 High Similarity NPC293183
0.9221 High Similarity NPC188203
0.9221 High Similarity NPC275722
0.9216 High Similarity NPC179183
0.9211 High Similarity NPC195202
0.9202 High Similarity NPC99591
0.9198 High Similarity NPC476370
0.9193 High Similarity NPC280493
0.9172 High Similarity NPC300943
0.9172 High Similarity NPC9609
0.9172 High Similarity NPC176300
0.9172 High Similarity NPC253634
0.9172 High Similarity NPC476410
0.9172 High Similarity NPC105242
0.9172 High Similarity NPC22472
0.9172 High Similarity NPC172202
0.9172 High Similarity NPC287458
0.9172 High Similarity NPC143828
0.9172 High Similarity NPC191459
0.9172 High Similarity NPC193842
0.9172 High Similarity NPC19687
0.9172 High Similarity NPC130894
0.9172 High Similarity NPC7846
0.9172 High Similarity NPC4481
0.9172 High Similarity NPC152166
0.9172 High Similarity NPC204854
0.9172 High Similarity NPC115798
0.9172 High Similarity NPC25495
0.9172 High Similarity NPC284127
0.9172 High Similarity NPC18772
0.9172 High Similarity NPC288669
0.9172 High Similarity NPC18607
0.9172 High Similarity NPC261004
0.9167 High Similarity NPC49824
0.9167 High Similarity NPC474520
0.9167 High Similarity NPC247017
0.9167 High Similarity NPC98661
0.9161 High Similarity NPC271779
0.9161 High Similarity NPC88645
0.9161 High Similarity NPC246204
0.9161 High Similarity NPC206238
0.9161 High Similarity NPC292214
0.9161 High Similarity NPC167091
0.9156 High Similarity NPC262623
0.915 High Similarity NPC92722
0.915 High Similarity NPC102003
0.9145 High Similarity NPC85233
0.9145 High Similarity NPC12200
0.9145 High Similarity NPC33265
0.9145 High Similarity NPC62536
0.9145 High Similarity NPC205522
0.9141 High Similarity NPC476374
0.9141 High Similarity NPC473834
0.9136 High Similarity NPC476365
0.913 High Similarity NPC295082
0.9125 High Similarity NPC280893
0.9119 High Similarity NPC83922
0.9119 High Similarity NPC472448
0.9119 High Similarity NPC219927
0.9119 High Similarity NPC477841
0.9114 High Similarity NPC98892
0.9114 High Similarity NPC476980
0.9108 High Similarity NPC472910
0.9108 High Similarity NPC163524
0.9108 High Similarity NPC78225
0.9108 High Similarity NPC287979
0.9108 High Similarity NPC29841
0.9108 High Similarity NPC470402
0.9108 High Similarity NPC472438
0.9108 High Similarity NPC48208
0.9108 High Similarity NPC176665
0.9108 High Similarity NPC474208
0.9108 High Similarity NPC305663
0.9108 High Similarity NPC474836
0.9108 High Similarity NPC96167
0.9108 High Similarity NPC472913
0.9108 High Similarity NPC472914
0.9108 High Similarity NPC99597
0.9108 High Similarity NPC7973
0.9108 High Similarity NPC156057
0.9108 High Similarity NPC245758
0.9108 High Similarity NPC101830
0.9108 High Similarity NPC162869
0.9108 High Similarity NPC36852
0.9108 High Similarity NPC472911
0.9108 High Similarity NPC235215
0.9108 High Similarity NPC203891
0.9108 High Similarity NPC210084
0.9108 High Similarity NPC475267
0.9108 High Similarity NPC222814
0.9108 High Similarity NPC110070
0.9108 High Similarity NPC262286
0.9108 High Similarity NPC78302
0.9103 High Similarity NPC26227
0.9103 High Similarity NPC44079
0.9103 High Similarity NPC255807
0.9103 High Similarity NPC201451
0.9103 High Similarity NPC31018
0.9097 High Similarity NPC257648
0.9097 High Similarity NPC161277
0.9097 High Similarity NPC101996
0.9097 High Similarity NPC199100
0.9097 High Similarity NPC477231
0.9097 High Similarity NPC180234
0.9097 High Similarity NPC39007
0.9097 High Similarity NPC120537

  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 NPC188967 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
0.9286 High Similarity NPD2801 Approved
0.8889 High Similarity NPD6167 Clinical (unspecified phase)
0.8889 High Similarity NPD6166 Phase 2
0.8889 High Similarity NPD6168 Clinical (unspecified phase)
0.8854 High Similarity NPD1934 Approved
0.8805 High Similarity NPD3882 Suspended
0.8701 High Similarity NPD1511 Approved
0.8688 High Similarity NPD4868 Clinical (unspecified phase)
0.8679 High Similarity NPD2393 Clinical (unspecified phase)
0.8642 High Similarity NPD5494 Approved
0.8625 High Similarity NPD3817 Phase 2
0.859 High Similarity NPD1512 Approved
0.8554 High Similarity NPD3818 Discontinued
0.8537 High Similarity NPD6232 Discontinued
0.8526 High Similarity NPD7410 Clinical (unspecified phase)
0.8521 High Similarity NPD4338 Clinical (unspecified phase)
0.8512 High Similarity NPD7993 Clinical (unspecified phase)
0.8503 High Similarity NPD7054 Approved
0.8494 Intermediate Similarity NPD7473 Discontinued
0.8452 Intermediate Similarity NPD7074 Phase 3
0.8452 Intermediate Similarity NPD7472 Approved
0.8412 Intermediate Similarity NPD7808 Phase 3
0.8408 Intermediate Similarity NPD4378 Clinical (unspecified phase)
0.8395 Intermediate Similarity NPD8443 Clinical (unspecified phase)
0.8393 Intermediate Similarity NPD5844 Phase 1
0.8375 Intermediate Similarity NPD4380 Phase 2
0.8364 Intermediate Similarity NPD6959 Discontinued
0.8323 Intermediate Similarity NPD7852 Clinical (unspecified phase)
0.8323 Intermediate Similarity NPD7411 Suspended
0.8294 Intermediate Similarity NPD6797 Phase 2
0.8293 Intermediate Similarity NPD4381 Clinical (unspecified phase)
0.8282 Intermediate Similarity NPD5402 Approved
0.8258 Intermediate Similarity NPD1549 Phase 2
0.8246 Intermediate Similarity NPD7251 Discontinued
0.8232 Intermediate Similarity NPD7768 Phase 2
0.8221 Intermediate Similarity NPD7819 Suspended
0.8194 Intermediate Similarity NPD1552 Clinical (unspecified phase)
0.8194 Intermediate Similarity NPD1550 Clinical (unspecified phase)
0.8182 Intermediate Similarity NPD1510 Phase 2
0.8182 Intermediate Similarity NPD7075 Discontinued
0.8158 Intermediate Similarity NPD1240 Approved
0.8155 Intermediate Similarity NPD3926 Phase 2
0.8129 Intermediate Similarity NPD2796 Approved
0.8125 Intermediate Similarity NPD8397 Clinical (unspecified phase)
0.8113 Intermediate Similarity NPD6799 Approved
0.811 Intermediate Similarity NPD1465 Phase 2
0.8075 Intermediate Similarity NPD6980 Clinical (unspecified phase)
0.8072 Intermediate Similarity NPD3749 Approved
0.8052 Intermediate Similarity NPD1607 Approved
0.8036 Intermediate Similarity NPD1247 Approved
0.8 Intermediate Similarity NPD7096 Clinical (unspecified phase)
0.7965 Intermediate Similarity NPD7804 Clinical (unspecified phase)
0.7939 Intermediate Similarity NPD6801 Discontinued
0.7922 Intermediate Similarity NPD943 Approved
0.7898 Intermediate Similarity NPD2935 Discontinued
0.7871 Intermediate Similarity NPD447 Suspended
0.7853 Intermediate Similarity NPD5403 Approved
0.7829 Intermediate Similarity NPD6559 Discontinued
0.7818 Intermediate Similarity NPD6599 Discontinued
0.7812 Intermediate Similarity NPD3750 Approved
0.7799 Intermediate Similarity NPD970 Clinical (unspecified phase)
0.7778 Intermediate Similarity NPD7390 Discontinued
0.775 Intermediate Similarity NPD7421 Clinical (unspecified phase)
0.7735 Intermediate Similarity NPD7879 Clinical (unspecified phase)
0.773 Intermediate Similarity NPD5401 Approved
0.7706 Intermediate Similarity NPD919 Approved
0.7673 Intermediate Similarity NPD1551 Phase 2
0.7669 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.7651 Intermediate Similarity NPD3226 Approved
0.7643 Intermediate Similarity NPD230 Phase 1
0.764 Intermediate Similarity NPD8312 Approved
0.764 Intermediate Similarity NPD8313 Approved
0.764 Intermediate Similarity NPD2800 Approved
0.7625 Intermediate Similarity NPD2344 Approved
0.7616 Intermediate Similarity NPD7199 Phase 2
0.76 Intermediate Similarity NPD3751 Discontinued
0.7572 Intermediate Similarity NPD3787 Discontinued
0.7564 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.7556 Intermediate Similarity NPD8055 Clinical (unspecified phase)
0.7548 Intermediate Similarity NPD1529 Clinical (unspecified phase)
0.7546 Intermediate Similarity NPD6190 Approved
0.754 Intermediate Similarity NPD7501 Clinical (unspecified phase)
0.7532 Intermediate Similarity NPD1933 Approved
0.7529 Intermediate Similarity NPD7184 Clinical (unspecified phase)
0.7515 Intermediate Similarity NPD2532 Approved
0.7515 Intermediate Similarity NPD2534 Approved
0.7515 Intermediate Similarity NPD2533 Approved
0.75 Intermediate Similarity NPD651 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD3748 Approved
0.75 Intermediate Similarity NPD1509 Clinical (unspecified phase)
0.7485 Intermediate Similarity NPD1878 Clinical (unspecified phase)
0.7485 Intermediate Similarity NPD1653 Approved
0.7484 Intermediate Similarity NPD1530 Clinical (unspecified phase)
0.7472 Intermediate Similarity NPD5953 Discontinued
0.7468 Intermediate Similarity NPD1613 Approved
0.7468 Intermediate Similarity NPD1612 Clinical (unspecified phase)
0.7439 Intermediate Similarity NPD2309 Approved
0.7436 Intermediate Similarity NPD4908 Phase 1
0.7425 Intermediate Similarity NPD920 Approved
0.7412 Intermediate Similarity NPD37 Approved
0.741 Intermediate Similarity NPD7422 Clinical (unspecified phase)
0.7399 Intermediate Similarity NPD6234 Discontinued
0.7391 Intermediate Similarity NPD2799 Discontinued
0.7389 Intermediate Similarity NPD3027 Phase 3
0.7384 Intermediate Similarity NPD4966 Approved
0.7384 Intermediate Similarity NPD4965 Approved
0.7384 Intermediate Similarity NPD4967 Phase 2
0.7382 Intermediate Similarity NPD7870 Phase 2
0.7382 Intermediate Similarity NPD7871 Phase 2
0.738 Intermediate Similarity NPD8090 Clinical (unspecified phase)
0.7378 Intermediate Similarity NPD4628 Phase 3
0.7375 Intermediate Similarity NPD6651 Approved
0.7372 Intermediate Similarity NPD9494 Approved
0.736 Intermediate Similarity NPD7286 Phase 2
0.7355 Intermediate Similarity NPD1203 Approved
0.7354 Intermediate Similarity NPD6777 Approved
0.7354 Intermediate Similarity NPD6778 Approved
0.7354 Intermediate Similarity NPD6779 Approved
0.7354 Intermediate Similarity NPD6782 Approved
0.7354 Intermediate Similarity NPD6776 Approved
0.7354 Intermediate Similarity NPD6781 Approved
0.7354 Intermediate Similarity NPD6780 Approved
0.7346 Intermediate Similarity NPD6099 Approved
0.7346 Intermediate Similarity NPD6100 Approved
0.7342 Intermediate Similarity NPD2313 Discontinued
0.7342 Intermediate Similarity NPD4907 Clinical (unspecified phase)
0.7338 Intermediate Similarity NPD4379 Clinical (unspecified phase)
0.7333 Intermediate Similarity NPD7685 Pre-registration
0.733 Intermediate Similarity NPD7697 Approved
0.733 Intermediate Similarity NPD7696 Phase 3
0.733 Intermediate Similarity NPD7698 Approved
0.7325 Intermediate Similarity NPD6832 Phase 2
0.732 Intermediate Similarity NPD8151 Discontinued
0.7317 Intermediate Similarity NPD1243 Approved
0.731 Intermediate Similarity NPD6844 Discontinued
0.7305 Intermediate Similarity NPD642 Clinical (unspecified phase)
0.7301 Intermediate Similarity NPD2346 Discontinued
0.724 Intermediate Similarity NPD7435 Discontinued
0.7239 Intermediate Similarity NPD5404 Approved
0.7239 Intermediate Similarity NPD5405 Approved
0.7239 Intermediate Similarity NPD5406 Approved
0.7239 Intermediate Similarity NPD5408 Approved
0.7232 Intermediate Similarity NPD5242 Approved
0.7228 Intermediate Similarity NPD8434 Phase 2
0.7228 Intermediate Similarity NPD8150 Discontinued
0.7216 Intermediate Similarity NPD8127 Discontinued
0.7207 Intermediate Similarity NPD7228 Approved
0.7205 Intermediate Similarity NPD1899 Clinical (unspecified phase)
0.7202 Intermediate Similarity NPD7004 Clinical (unspecified phase)
0.7198 Intermediate Similarity NPD7549 Discontinued
0.7198 Intermediate Similarity NPD4419 Clinical (unspecified phase)
0.7188 Intermediate Similarity NPD6233 Phase 2
0.7186 Intermediate Similarity NPD643 Clinical (unspecified phase)
0.7179 Intermediate Similarity NPD7701 Phase 2
0.7169 Intermediate Similarity NPD6398 Clinical (unspecified phase)
0.7168 Intermediate Similarity NPD8455 Phase 2
0.7161 Intermediate Similarity NPD9717 Approved
0.7157 Intermediate Similarity NPD7782 Clinical (unspecified phase)
0.7157 Intermediate Similarity NPD7783 Phase 2
0.7152 Intermediate Similarity NPD3018 Phase 2
0.7151 Intermediate Similarity NPD4287 Approved
0.7151 Intermediate Similarity NPD6385 Approved
0.7151 Intermediate Similarity NPD6386 Approved
0.7143 Intermediate Similarity NPD4357 Discontinued
0.7135 Intermediate Similarity NPD7458 Discontinued
0.7126 Intermediate Similarity NPD5353 Approved
0.7107 Intermediate Similarity NPD7874 Approved
0.7107 Intermediate Similarity NPD7875 Clinical (unspecified phase)
0.7105 Intermediate Similarity NPD5536 Phase 2
0.7098 Intermediate Similarity NPD6823 Phase 2
0.7097 Intermediate Similarity NPD1547 Clinical (unspecified phase)
0.7095 Intermediate Similarity NPD7784 Clinical (unspecified phase)
0.709 Intermediate Similarity NPD6534 Approved
0.709 Intermediate Similarity NPD6535 Approved
0.7089 Intermediate Similarity NPD2798 Approved
0.7079 Intermediate Similarity NPD7229 Phase 3
0.7071 Intermediate Similarity NPD7801 Approved
0.7068 Intermediate Similarity NPD7699 Phase 2
0.7068 Intermediate Similarity NPD7700 Phase 2
0.7059 Intermediate Similarity NPD1548 Phase 1
0.7051 Intermediate Similarity NPD9269 Phase 2
0.7049 Intermediate Similarity NPD7039 Approved
0.7049 Intermediate Similarity NPD7038 Approved
0.7045 Intermediate Similarity NPD6971 Discontinued
0.7035 Intermediate Similarity NPD5808 Clinical (unspecified phase)
0.7025 Intermediate Similarity NPD1470 Approved
0.7019 Intermediate Similarity NPD3268 Approved
0.7019 Intermediate Similarity NPD411 Approved
0.7019 Intermediate Similarity NPD3764 Approved
0.7019 Intermediate Similarity NPD6798 Discontinued
0.7017 Intermediate Similarity NPD7177 Discontinued
0.7013 Intermediate Similarity NPD9268 Approved
0.7006 Intermediate Similarity NPD2982 Phase 2
0.7006 Intermediate Similarity NPD2654 Approved
0.7006 Intermediate Similarity NPD2983 Phase 2
0.7 Intermediate Similarity NPD2403 Approved
0.7 Intermediate Similarity NPD4363 Phase 3
0.7 Intermediate Similarity NPD4360 Phase 2
0.6987 Remote Similarity NPD422 Phase 1
0.6987 Remote Similarity NPD1610 Phase 2

  Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity
B: biological targets similarity
C: networks similarity
D: cell-based bioactivity similarity
E: similarity based on clinical data