Structure

Physi-Chem Properties

Molecular Weight:  432.14
Volume:  421.419
LogP:  2.822
LogD:  2.731
LogS:  -4.044
# Rotatable Bonds:  8
TPSA:  94.82
# H-Bond Aceptor:  9
# H-Bond Donor:  0
# Rings:  3
# Heavy Atoms:  9

MedChem Properties

QED Drug-Likeness Score:  0.53
Synthetic Accessibility Score:  2.578
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:  -4.541
MDCK Permeability:  2.129799031536095e-05
Pgp-inhibitor:  0.999
Pgp-substrate:  0.0
Human Intestinal Absorption (HIA):  0.018
20% Bioavailability (F20%):  0.001
30% Bioavailability (F30%):  0.006

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.069
Plasma Protein Binding (PPB):  64.93891143798828%
Volume Distribution (VD):  0.909
Pgp-substrate:  45.925350189208984%

ADMET: Metabolism

CYP1A2-inhibitor:  0.108
CYP1A2-substrate:  0.992
CYP2C19-inhibitor:  0.273
CYP2C19-substrate:  0.921
CYP2C9-inhibitor:  0.391
CYP2C9-substrate:  0.903
CYP2D6-inhibitor:  0.0
CYP2D6-substrate:  0.916
CYP3A4-inhibitor:  0.477
CYP3A4-substrate:  0.886

ADMET: Excretion

Clearance (CL):  4.244
Half-life (T1/2):  0.375

ADMET: Toxicity

hERG Blockers:  0.411
Human Hepatotoxicity (H-HT):  0.051
Drug-inuced Liver Injury (DILI):  0.856
AMES Toxicity:  0.093
Rat Oral Acute Toxicity:  0.287
Maximum Recommended Daily Dose:  0.023
Skin Sensitization:  0.383
Carcinogencity:  0.042
Eye Corrosion:  0.003
Eye Irritation:  0.073
Respiratory Toxicity:  0.026

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

  Natural Product: NPC283002

Natural Product ID:  NPC283002
Common Name*:   Hepatamethoxyflavone
IUPAC Name:   5,6,7,8-tetramethoxy-2-(3,4,5-trimethoxyphenyl)chromen-4-one
Synonyms:   NSC-67580
Standard InCHIKey:  UAELIRBOLQZEAT-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C22H24O9/c1-24-14-8-11(9-15(25-2)17(14)26-3)13-10-12(23)16-18(27-4)20(28-5)22(30-7)21(29-6)19(16)31-13/h8-10H,1-7H3
SMILES:  COc1c(OC)cc(cc1OC)c1cc(=O)c2c(o1)c(OC)c(c(c2OC)OC)OC
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL310982
PubChem CID:   72815
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
NPO13624 Ageratum corymbosum Species Asteraceae Eukaryota n.a. n.a. n.a. DOI[10.1016/S0031-9422(00)91044-6]
NPO13624 Ageratum corymbosum Species Asteraceae 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
NPT517 Cell Line Panel NCI-60 (60 carcinoma cell lines) Homo sapiens GI50 = 32000.0 nM PMID[458827]
NPT91 Cell Line KB Homo sapiens ED50 = 0.5 ug ml-1 PMID[458828]
NPT368 Cell Line SN12C Homo sapiens GI50 n.a. 43551.19 nM PMID[458829]
NPT367 Cell Line MDA-N Homo sapiens GI50 n.a. 42657.95 nM PMID[458829]
NPT369 Cell Line ACHN Homo sapiens GI50 n.a. 21877.62 nM PMID[458829]
NPT370 Cell Line NCI-H23 Homo sapiens GI50 n.a. 41783.04 nM PMID[458829]
NPT371 Cell Line UO-31 Homo sapiens GI50 n.a. 7379.04 nM PMID[458829]
NPT372 Cell Line HOP-92 Homo sapiens GI50 n.a. 9977.0 nM PMID[458829]
NPT90 Cell Line DU-145 Homo sapiens GI50 n.a. 45498.81 nM PMID[458829]
NPT116 Cell Line HL-60 Homo sapiens GI50 n.a. 15031.42 nM PMID[458829]
NPT373 Cell Line SK-MEL-5 Homo sapiens GI50 n.a. 12445.15 nM PMID[458829]
NPT374 Cell Line SF-539 Homo sapiens GI50 n.a. 100000.0 nM PMID[458829]
NPT375 Cell Line Malme-3M Homo sapiens GI50 n.a. 39627.8 nM PMID[458829]
NPT376 Cell Line A498 Homo sapiens GI50 n.a. 21183.61 nM PMID[458829]
NPT111 Cell Line K562 Homo sapiens GI50 n.a. 63386.97 nM PMID[458829]
NPT377 Cell Line OVCAR-3 Homo sapiens GI50 n.a. 25468.3 nM PMID[458829]
NPT112 Cell Line MOLT-4 Homo sapiens GI50 n.a. 24945.95 nM PMID[458829]
NPT378 Cell Line NCI/ADR-RES Homo sapiens GI50 n.a. 23550.49 nM PMID[458829]
NPT379 Cell Line HOP-62 Homo sapiens GI50 n.a. 41879.36 nM PMID[458829]
NPT380 Cell Line U-251 Homo sapiens GI50 n.a. 40086.67 nM PMID[458829]
NPT381 Cell Line OVCAR-8 Homo sapiens GI50 n.a. 24547.09 nM PMID[458829]
NPT382 Cell Line OVCAR-5 Homo sapiens GI50 n.a. 100000.0 nM PMID[458829]
NPT383 Cell Line SNB-19 Homo sapiens GI50 n.a. 76559.66 nM PMID[458829]
NPT82 Cell Line MDA-MB-231 Homo sapiens GI50 n.a. 31622.78 nM PMID[458829]
NPT384 Cell Line TK-10 Homo sapiens GI50 n.a. 44360.86 nM PMID[458829]
NPT385 Cell Line SR Homo sapiens GI50 n.a. 100000.0 nM PMID[458829]
NPT323 Cell Line SW-620 Homo sapiens GI50 n.a. 54954.09 nM PMID[458829]
NPT455 Cell Line NCI-H522 Homo sapiens GI50 n.a. 19098.53 nM PMID[458829]
NPT387 Cell Line M14 Homo sapiens GI50 n.a. 45708.82 nM PMID[458829]
NPT388 Cell Line NCI-H322M Homo sapiens GI50 n.a. 58884.37 nM PMID[458829]
NPT389 Cell Line RPMI-8226 Homo sapiens GI50 n.a. 26061.54 nM PMID[458829]
NPT456 Cell Line OVCAR-4 Homo sapiens GI50 n.a. 32359.37 nM PMID[458829]
NPT390 Cell Line LOX IMVI Homo sapiens GI50 n.a. 25941.79 nM PMID[458829]
NPT457 Cell Line BT-549 Homo sapiens GI50 n.a. 48640.72 nM PMID[458829]
NPT147 Cell Line SK-MEL-2 Homo sapiens GI50 n.a. 27861.21 nM PMID[458829]
NPT391 Cell Line HCC 2998 Homo sapiens GI50 n.a. 30269.13 nM PMID[458829]
NPT81 Cell Line A549 Homo sapiens GI50 n.a. 35481.34 nM PMID[458829]
NPT392 Cell Line SNB-75 Homo sapiens GI50 n.a. 26363.31 nM PMID[458829]
NPT148 Cell Line HCT-15 Homo sapiens GI50 n.a. 33419.5 nM PMID[458829]
NPT393 Cell Line HCT-116 Homo sapiens GI50 n.a. 44771.33 nM PMID[458829]
NPT394 Cell Line EKVX Homo sapiens GI50 n.a. 48417.24 nM PMID[458829]
NPT395 Cell Line SF-268 Homo sapiens GI50 n.a. 32885.16 nM PMID[458829]
NPT83 Cell Line MCF7 Homo sapiens GI50 n.a. 84333.48 nM PMID[458829]
NPT146 Cell Line SK-OV-3 Homo sapiens GI50 n.a. 3872.58 nM PMID[458829]
NPT396 Cell Line T47D Homo sapiens GI50 n.a. 12735.03 nM PMID[458829]
NPT397 Cell Line NCI-H460 Homo sapiens GI50 n.a. 42266.86 nM PMID[458829]
NPT308 Cell Line CAKI-1 Homo sapiens GI50 n.a. 21627.19 nM PMID[458829]
NPT398 Cell Line UACC-62 Homo sapiens GI50 n.a. 21037.78 nM PMID[458829]
NPT400 Cell Line MDA-MB-435 Homo sapiens GI50 n.a. 29040.23 nM PMID[458829]
NPT399 Cell Line SF-295 Homo sapiens GI50 n.a. 28119.01 nM PMID[458829]
NPT458 Cell Line IGROV-1 Homo sapiens GI50 n.a. 52239.62 nM PMID[458829]
NPT401 Cell Line 786-0 Homo sapiens GI50 n.a. 58884.37 nM PMID[458829]
NPT402 Cell Line Hs-578T Homo sapiens GI50 n.a. 28973.44 nM PMID[458829]
NPT403 Cell Line UACC-257 Homo sapiens GI50 n.a. 39994.47 nM PMID[458829]
NPT404 Cell Line CCRF-CEM Homo sapiens GI50 n.a. 30478.95 nM PMID[458829]
NPT139 Cell Line HT-29 Homo sapiens GI50 n.a. 35892.19 nM PMID[458829]
NPT405 Cell Line NCI-H226 Homo sapiens GI50 n.a. 44771.33 nM PMID[458829]
NPT170 Cell Line SK-MEL-28 Homo sapiens GI50 n.a. 53210.83 nM PMID[458829]
NPT406 Cell Line RXF 393 Homo sapiens GI50 n.a. 28119.01 nM PMID[458829]
NPT407 Cell Line COLO 205 Homo sapiens GI50 n.a. 18706.82 nM PMID[458829]

☑ 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 NPC283002 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 NPC302408
0.9929 High Similarity NPC85233
0.9928 High Similarity NPC165512
0.9857 High Similarity NPC14958
0.9857 High Similarity NPC40818
0.9857 High Similarity NPC106461
0.9857 High Similarity NPC215932
0.9857 High Similarity NPC110639
0.9789 High Similarity NPC181250
0.9787 High Similarity NPC205522
0.972 High Similarity NPC201547
0.972 High Similarity NPC259058
0.9714 High Similarity NPC23955
0.9712 High Similarity NPC29536
0.965 High Similarity NPC69752
0.9645 High Similarity NPC136278
0.9643 High Similarity NPC70853
0.9643 High Similarity NPC9966
0.9586 High Similarity NPC134677
0.958 High Similarity NPC63256
0.958 High Similarity NPC10304
0.9574 High Similarity NPC113089
0.9571 High Similarity NPC124467
0.9571 High Similarity NPC214919
0.9521 High Similarity NPC276409
0.9521 High Similarity NPC75279
0.9521 High Similarity NPC250822
0.9517 High Similarity NPC226973
0.9517 High Similarity NPC208043
0.9514 High Similarity NPC238366
0.9514 High Similarity NPC328119
0.9456 High Similarity NPC128863
0.9456 High Similarity NPC167815
0.9456 High Similarity NPC50715
0.9456 High Similarity NPC241774
0.9456 High Similarity NPC201136
0.9456 High Similarity NPC227325
0.9456 High Similarity NPC208197
0.9456 High Similarity NPC146165
0.9456 High Similarity NPC34725
0.9456 High Similarity NPC4455
0.9456 High Similarity NPC2476
0.9456 High Similarity NPC92659
0.9456 High Similarity NPC163780
0.9456 High Similarity NPC196439
0.9456 High Similarity NPC138360
0.9456 High Similarity NPC280339
0.9456 High Similarity NPC183597
0.9456 High Similarity NPC276059
0.9456 High Similarity NPC122623
0.9448 High Similarity NPC306821
0.9441 High Similarity NPC310259
0.9441 High Similarity NPC231013
0.9441 High Similarity NPC216314
0.9441 High Similarity NPC120924
0.9441 High Similarity NPC195919
0.9437 High Similarity NPC182842
0.9392 High Similarity NPC178854
0.9392 High Similarity NPC474520
0.9392 High Similarity NPC257277
0.9388 High Similarity NPC47781
0.9388 High Similarity NPC274327
0.9388 High Similarity NPC231018
0.9388 High Similarity NPC255350
0.9388 High Similarity NPC186507
0.9388 High Similarity NPC246204
0.9388 High Similarity NPC69394
0.9388 High Similarity NPC145379
0.9388 High Similarity NPC22519
0.9388 High Similarity NPC280937
0.9388 High Similarity NPC160951
0.9388 High Similarity NPC476289
0.9388 High Similarity NPC472408
0.9388 High Similarity NPC183878
0.9388 High Similarity NPC86485
0.9388 High Similarity NPC176775
0.9384 High Similarity NPC474663
0.9384 High Similarity NPC308451
0.9375 High Similarity NPC299923
0.9375 High Similarity NPC62536
0.9375 High Similarity NPC33265
0.9371 High Similarity NPC471590
0.9362 High Similarity NPC58229
0.9329 High Similarity NPC224137
0.9329 High Similarity NPC29841
0.9329 High Similarity NPC235215
0.9329 High Similarity NPC93376
0.9329 High Similarity NPC227192
0.9329 High Similarity NPC189179
0.9329 High Similarity NPC472438
0.9329 High Similarity NPC7973
0.9329 High Similarity NPC78302
0.9329 High Similarity NPC75215
0.9324 High Similarity NPC213622
0.9324 High Similarity NPC32557
0.9324 High Similarity NPC20830
0.9324 High Similarity NPC189960
0.9324 High Similarity NPC256612
0.932 High Similarity NPC241498
0.932 High Similarity NPC100887
0.932 High Similarity NPC25270
0.932 High Similarity NPC188203
0.932 High Similarity NPC239128
0.932 High Similarity NPC198826
0.932 High Similarity NPC301123
0.932 High Similarity NPC131624
0.932 High Similarity NPC71334
0.932 High Similarity NPC187498
0.932 High Similarity NPC142540
0.932 High Similarity NPC120163
0.932 High Similarity NPC212678
0.932 High Similarity NPC222830
0.932 High Similarity NPC275722
0.932 High Similarity NPC57030
0.932 High Similarity NPC301323
0.932 High Similarity NPC292460
0.932 High Similarity NPC156222
0.932 High Similarity NPC83508
0.932 High Similarity NPC162313
0.932 High Similarity NPC293183
0.932 High Similarity NPC256283
0.932 High Similarity NPC275836
0.932 High Similarity NPC166201
0.9315 High Similarity NPC219330
0.9315 High Similarity NPC29056
0.931 High Similarity NPC261548
0.931 High Similarity NPC195202
0.9301 High Similarity NPC293201
0.9267 High Similarity NPC22472
0.9267 High Similarity NPC104459
0.9267 High Similarity NPC238405
0.9267 High Similarity NPC130894
0.9267 High Similarity NPC18772
0.9267 High Similarity NPC7846
0.9267 High Similarity NPC300943
0.9267 High Similarity NPC18607
0.9267 High Similarity NPC115798
0.9267 High Similarity NPC105242
0.9267 High Similarity NPC9609
0.9267 High Similarity NPC261004
0.9267 High Similarity NPC19687
0.9267 High Similarity NPC191459
0.9267 High Similarity NPC288669
0.9267 High Similarity NPC143828
0.9267 High Similarity NPC152166
0.9267 High Similarity NPC4481
0.9267 High Similarity NPC176300
0.9267 High Similarity NPC253634
0.9267 High Similarity NPC257914
0.9267 High Similarity NPC204854
0.9267 High Similarity NPC25495
0.9262 High Similarity NPC100916
0.9262 High Similarity NPC49824
0.9262 High Similarity NPC247017
0.9262 High Similarity NPC98661
0.9262 High Similarity NPC200388
0.9262 High Similarity NPC55619
0.9262 High Similarity NPC268161
0.9257 High Similarity NPC472915
0.9257 High Similarity NPC128961
0.9252 High Similarity NPC474170
0.9252 High Similarity NPC474388
0.9252 High Similarity NPC472535
0.9252 High Similarity NPC198615
0.9252 High Similarity NPC117579
0.9252 High Similarity NPC76376
0.9247 High Similarity NPC48479
0.9247 High Similarity NPC177298
0.9241 High Similarity NPC12200
0.92 High Similarity NPC110070
0.92 High Similarity NPC476981
0.92 High Similarity NPC305663
0.92 High Similarity NPC287979
0.92 High Similarity NPC203891
0.92 High Similarity NPC163524
0.92 High Similarity NPC19097
0.92 High Similarity NPC176665
0.92 High Similarity NPC470402
0.92 High Similarity NPC101830
0.9195 High Similarity NPC201451
0.9195 High Similarity NPC37392
0.9195 High Similarity NPC44079
0.9195 High Similarity NPC26227
0.9195 High Similarity NPC472909
0.9189 High Similarity NPC39732
0.9189 High Similarity NPC60972
0.9184 High Similarity NPC239363
0.9184 High Similarity NPC50728
0.9184 High Similarity NPC177839
0.9184 High Similarity NPC166753
0.9184 High Similarity NPC179183
0.9184 High Similarity NPC184136
0.9178 High Similarity NPC476058
0.9178 High Similarity NPC476342
0.9178 High Similarity NPC120464
0.9161 High Similarity NPC185607
0.9149 High Similarity NPC44573
0.9139 High Similarity NPC190487
0.9139 High Similarity NPC193842
0.9139 High Similarity NPC154304

  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 NPC283002 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
0.9388 High Similarity NPD2801 Approved
0.9067 High Similarity NPD3817 Phase 2
0.8954 High Similarity NPD5494 Approved
0.8808 High Similarity NPD1934 Approved
0.8776 High Similarity NPD1511 Approved
0.8681 High Similarity NPD2796 Approved
0.8658 High Similarity NPD1512 Approved
0.8636 High Similarity NPD3882 Suspended
0.8627 High Similarity NPD2393 Clinical (unspecified phase)
0.8535 High Similarity NPD1247 Approved
0.85 High Similarity NPD3818 Discontinued
0.8491 Intermediate Similarity NPD6168 Clinical (unspecified phase)
0.8491 Intermediate Similarity NPD6166 Phase 2
0.8491 Intermediate Similarity NPD6167 Clinical (unspecified phase)
0.8467 Intermediate Similarity NPD4378 Clinical (unspecified phase)
0.8466 Intermediate Similarity NPD4338 Clinical (unspecified phase)
0.8447 Intermediate Similarity NPD7054 Approved
0.8428 Intermediate Similarity NPD3926 Phase 2
0.8395 Intermediate Similarity NPD7472 Approved
0.8333 Intermediate Similarity NPD5402 Approved
0.8282 Intermediate Similarity NPD7074 Phase 3
0.828 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.8278 Intermediate Similarity NPD6799 Approved
0.825 Intermediate Similarity NPD6232 Discontinued
0.8242 Intermediate Similarity NPD7808 Phase 3
0.8235 Intermediate Similarity NPD6980 Clinical (unspecified phase)
0.8232 Intermediate Similarity NPD6797 Phase 2
0.821 Intermediate Similarity NPD7473 Discontinued
0.8194 Intermediate Similarity NPD4380 Phase 2
0.8182 Intermediate Similarity NPD7251 Discontinued
0.8176 Intermediate Similarity NPD919 Approved
0.8153 Intermediate Similarity NPD7819 Suspended
0.8121 Intermediate Similarity NPD1552 Clinical (unspecified phase)
0.8121 Intermediate Similarity NPD1550 Clinical (unspecified phase)
0.8113 Intermediate Similarity NPD4381 Clinical (unspecified phase)
0.8108 Intermediate Similarity NPD1510 Phase 2
0.8105 Intermediate Similarity NPD7410 Clinical (unspecified phase)
0.8089 Intermediate Similarity NPD6801 Discontinued
0.8067 Intermediate Similarity NPD1549 Phase 2
0.8038 Intermediate Similarity NPD7096 Clinical (unspecified phase)
0.8 Intermediate Similarity NPD7075 Discontinued
0.8 Intermediate Similarity NPD5844 Phase 1
0.7962 Intermediate Similarity NPD6599 Discontinued
0.7959 Intermediate Similarity NPD1240 Approved
0.7947 Intermediate Similarity NPD970 Clinical (unspecified phase)
0.7925 Intermediate Similarity NPD1465 Phase 2
0.7911 Intermediate Similarity NPD7411 Suspended
0.7905 Intermediate Similarity NPD1933 Approved
0.7895 Intermediate Similarity NPD1243 Approved
0.7885 Intermediate Similarity NPD920 Approved
0.7885 Intermediate Similarity NPD5403 Approved
0.7875 Intermediate Similarity NPD8443 Clinical (unspecified phase)
0.7871 Intermediate Similarity NPD5401 Approved
0.7867 Intermediate Similarity NPD3748 Approved
0.7853 Intermediate Similarity NPD6959 Discontinued
0.7852 Intermediate Similarity NPD1607 Approved
0.7798 Intermediate Similarity NPD7993 Clinical (unspecified phase)
0.7785 Intermediate Similarity NPD447 Suspended
0.7784 Intermediate Similarity NPD7804 Clinical (unspecified phase)
0.7756 Intermediate Similarity NPD642 Clinical (unspecified phase)
0.7718 Intermediate Similarity NPD943 Approved
0.7703 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.7697 Intermediate Similarity NPD2935 Discontinued
0.7687 Intermediate Similarity NPD6832 Phase 2
0.7662 Intermediate Similarity NPD2800 Approved
0.7628 Intermediate Similarity NPD643 Clinical (unspecified phase)
0.7613 Intermediate Similarity NPD3750 Approved
0.755 Intermediate Similarity NPD230 Phase 1
0.755 Intermediate Similarity NPD1899 Clinical (unspecified phase)
0.7548 Intermediate Similarity NPD2654 Approved
0.7546 Intermediate Similarity NPD5353 Approved
0.7545 Intermediate Similarity NPD5242 Approved
0.7544 Intermediate Similarity NPD6559 Discontinued
0.7532 Intermediate Similarity NPD2534 Approved
0.7532 Intermediate Similarity NPD2533 Approved
0.7532 Intermediate Similarity NPD2532 Approved
0.753 Intermediate Similarity NPD7199 Phase 2
0.75 Intermediate Similarity NPD7852 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD1530 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD2403 Approved
0.75 Intermediate Similarity NPD3018 Phase 2
0.7469 Intermediate Similarity NPD6385 Approved
0.7469 Intermediate Similarity NPD6386 Approved
0.7468 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.7468 Intermediate Similarity NPD1551 Phase 2
0.7467 Intermediate Similarity NPD2313 Discontinued
0.7465 Intermediate Similarity NPD5536 Phase 2
0.7455 Intermediate Similarity NPD3749 Approved
0.7453 Intermediate Similarity NPD3226 Approved
0.745 Intermediate Similarity NPD1529 Clinical (unspecified phase)
0.7448 Intermediate Similarity NPD1547 Clinical (unspecified phase)
0.744 Intermediate Similarity NPD7184 Clinical (unspecified phase)
0.7436 Intermediate Similarity NPD7421 Clinical (unspecified phase)
0.7423 Intermediate Similarity NPD37 Approved
0.7403 Intermediate Similarity NPD2799 Discontinued
0.7397 Intermediate Similarity NPD2981 Phase 2
0.7394 Intermediate Similarity NPD4965 Approved
0.7394 Intermediate Similarity NPD7768 Phase 2
0.7394 Intermediate Similarity NPD4966 Approved
0.7394 Intermediate Similarity NPD4967 Phase 2
0.7391 Intermediate Similarity NPD1653 Approved
0.7389 Intermediate Similarity NPD1878 Clinical (unspecified phase)
0.7386 Intermediate Similarity NPD6651 Approved
0.7381 Intermediate Similarity NPD3787 Discontinued
0.7368 Intermediate Similarity NPD1612 Clinical (unspecified phase)
0.7368 Intermediate Similarity NPD1613 Approved
0.7363 Intermediate Similarity NPD7501 Clinical (unspecified phase)
0.7355 Intermediate Similarity NPD6100 Approved
0.7355 Intermediate Similarity NPD6099 Approved
0.7347 Intermediate Similarity NPD2983 Phase 2
0.7347 Intermediate Similarity NPD2982 Phase 2
0.7345 Intermediate Similarity NPD8397 Clinical (unspecified phase)
0.7317 Intermediate Similarity NPD6844 Discontinued
0.7315 Intermediate Similarity NPD2798 Approved
0.731 Intermediate Similarity NPD3751 Discontinued
0.7308 Intermediate Similarity NPD2346 Discontinued
0.7308 Intermediate Similarity NPD2344 Approved
0.7305 Intermediate Similarity NPD6234 Discontinued
0.7294 Intermediate Similarity NPD7784 Clinical (unspecified phase)
0.729 Intermediate Similarity NPD651 Clinical (unspecified phase)
0.729 Intermediate Similarity NPD1509 Clinical (unspecified phase)
0.7285 Intermediate Similarity NPD3027 Phase 3
0.7283 Intermediate Similarity NPD5953 Discontinued
0.7278 Intermediate Similarity NPD4628 Phase 3
0.7267 Intermediate Similarity NPD1940 Clinical (unspecified phase)
0.725 Intermediate Similarity NPD7390 Discontinued
0.7248 Intermediate Similarity NPD3267 Approved
0.7248 Intermediate Similarity NPD3266 Approved
0.7233 Intermediate Similarity NPD6190 Approved
0.72 Intermediate Similarity NPD4419 Clinical (unspecified phase)
0.7192 Intermediate Similarity NPD17 Approved
0.7168 Intermediate Similarity NPD7286 Phase 2
0.7167 Intermediate Similarity NPD7879 Clinical (unspecified phase)
0.7162 Intermediate Similarity NPD3972 Approved
0.7152 Intermediate Similarity NPD9494 Approved
0.7143 Intermediate Similarity NPD4307 Phase 2
0.7133 Intermediate Similarity NPD1203 Approved
0.7125 Intermediate Similarity NPD2309 Approved
0.7124 Intermediate Similarity NPD3268 Approved
0.7124 Intermediate Similarity NPD1296 Phase 2
0.7114 Intermediate Similarity NPD4379 Clinical (unspecified phase)
0.7089 Intermediate Similarity NPD1471 Phase 3
0.7086 Intermediate Similarity NPD1019 Discontinued
0.7083 Intermediate Similarity NPD5019 Clinical (unspecified phase)
0.7079 Intermediate Similarity NPD8055 Clinical (unspecified phase)
0.7078 Intermediate Similarity NPD6233 Phase 2
0.707 Intermediate Similarity NPD7033 Discontinued
0.7063 Intermediate Similarity NPD5283 Phase 1
0.7063 Intermediate Similarity NPD1241 Discontinued
0.7063 Intermediate Similarity NPD6398 Clinical (unspecified phase)
0.7055 Intermediate Similarity NPD1548 Phase 1
0.7047 Intermediate Similarity NPD1608 Approved
0.7047 Intermediate Similarity NPD9717 Approved
0.7045 Intermediate Similarity NPD7685 Pre-registration
0.7039 Intermediate Similarity NPD8434 Phase 2
0.7037 Intermediate Similarity NPD4357 Discontinued
0.7025 Intermediate Similarity NPD3539 Phase 1
0.702 Intermediate Similarity NPD2797 Approved
0.7011 Intermediate Similarity NPD7228 Approved
0.7007 Intermediate Similarity NPD9268 Approved
0.6994 Remote Similarity NPD3688 Clinical (unspecified phase)
0.6994 Remote Similarity NPD3146 Approved
0.6993 Remote Similarity NPD4908 Phase 1
0.6981 Remote Similarity NPD3540 Phase 1
0.698 Remote Similarity NPD422 Phase 1
0.6977 Remote Similarity NPD7229 Phase 3
0.6977 Remote Similarity NPD5710 Approved
0.6977 Remote Similarity NPD5711 Approved
0.6962 Remote Similarity NPD4308 Phase 3
0.6954 Remote Similarity NPD3225 Approved
0.6933 Remote Similarity NPD9269 Phase 2
0.6923 Remote Similarity NPD4288 Approved
0.6923 Remote Similarity NPD5977 Approved
0.6923 Remote Similarity NPD5978 Approved
0.6919 Remote Similarity NPD8090 Clinical (unspecified phase)
0.6915 Remote Similarity NPD5006 Approved
0.6915 Remote Similarity NPD5005 Approved
0.6914 Remote Similarity NPD3887 Approved
0.691 Remote Similarity NPD7549 Discontinued
0.6905 Remote Similarity NPD6280 Approved
0.6905 Remote Similarity NPD6279 Approved
0.6903 Remote Similarity NPD4907 Clinical (unspecified phase)
0.6903 Remote Similarity NPD411 Approved
0.6903 Remote Similarity NPD6798 Discontinued
0.6902 Remote Similarity NPD4363 Phase 3
0.6902 Remote Similarity NPD4360 Phase 2
0.6898 Remote Similarity NPD6779 Approved
0.6898 Remote Similarity NPD6781 Approved
0.6898 Remote Similarity NPD6782 Approved
0.6898 Remote Similarity NPD6780 Approved
0.6898 Remote Similarity NPD6778 Approved
0.6898 Remote Similarity NPD6777 Approved
0.6898 Remote Similarity NPD6776 Approved
0.6894 Remote Similarity NPD1652 Phase 2
0.689 Remote Similarity NPD7422 Clinical (unspecified phase)
0.689 Remote Similarity NPD7004 Clinical (unspecified phase)
0.6883 Remote Similarity NPD1008 Clinical (unspecified phase)
0.6875 Remote Similarity NPD2355 Clinical (unspecified phase)
0.6875 Remote Similarity NPD2353 Approved
0.6872 Remote Similarity NPD8313 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