Structure

Physi-Chem Properties

Molecular Weight:  436.15
Volume:  441.897
LogP:  5.626
LogD:  3.511
LogS:  -2.768
# Rotatable Bonds:  3
TPSA:  120.36
# H-Bond Aceptor:  7
# H-Bond Donor:  4
# Rings:  4
# Heavy Atoms:  7

MedChem Properties

QED Drug-Likeness Score:  0.26
Synthetic Accessibility Score:  3.395
Fsp3:  0.24
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  1
PAINS Alert:  1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.98
MDCK Permeability:  1.4397830454981886e-05
Pgp-inhibitor:  0.315
Pgp-substrate:  0.013
Human Intestinal Absorption (HIA):  0.135
20% Bioavailability (F20%):  0.138
30% Bioavailability (F30%):  0.491

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.005
Plasma Protein Binding (PPB):  95.36846160888672%
Volume Distribution (VD):  0.567
Pgp-substrate:  5.669363498687744%

ADMET: Metabolism

CYP1A2-inhibitor:  0.775
CYP1A2-substrate:  0.177
CYP2C19-inhibitor:  0.56
CYP2C19-substrate:  0.053
CYP2C9-inhibitor:  0.831
CYP2C9-substrate:  0.799
CYP2D6-inhibitor:  0.651
CYP2D6-substrate:  0.221
CYP3A4-inhibitor:  0.234
CYP3A4-substrate:  0.092

ADMET: Excretion

Clearance (CL):  6.149
Half-life (T1/2):  0.562

ADMET: Toxicity

hERG Blockers:  0.015
Human Hepatotoxicity (H-HT):  0.931
Drug-inuced Liver Injury (DILI):  0.984
AMES Toxicity:  0.628
Rat Oral Acute Toxicity:  0.51
Maximum Recommended Daily Dose:  0.901
Skin Sensitization:  0.576
Carcinogencity:  0.731
Eye Corrosion:  0.003
Eye Irritation:  0.749
Respiratory Toxicity:  0.34

Download Data

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

  Natural Product: NPC276444

Natural Product ID:  NPC276444
Common Name*:   Artonin E
IUPAC Name:   5-hydroxy-8,8-dimethyl-3-(3-methylbut-2-enyl)-2-(2,4,5-trihydroxyphenyl)pyrano[2,3-h]chromen-4-one
Synonyms:   Artonin E
Standard InCHIKey:  HDHRTQZSBFUBMJ-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C25H24O7/c1-12(2)5-6-14-22(30)21-19(29)11-20-13(7-8-25(3,4)32-20)24(21)31-23(14)15-9-17(27)18(28)10-16(15)26/h5,7-11,26-29H,6H2,1-4H3
SMILES:  CC(=CCc1c(oc2c(c1=O)c(O)cc1c2C=CC(O1)(C)C)c1cc(O)c(cc1O)O)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL463106
PubChem CID:   5481962
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000261] Phenylpropanoids and polyketides
      • [CHEMONTID:0000334] Flavonoids
        • [CHEMONTID:0001615] Flavones
          • [CHEMONTID:0003501] 3-prenylated flavones

*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
NPO28803 Artocarpus chama Species Moraceae Eukaryota n.a. root n.a. PMID[15165133]
NPO33150 Artocarpus communis Species Moraceae Eukaryota heartwood n.a. n.a. PMID[16643064]
NPO15265 Paeonia rockii Species Paeoniaceae Eukaryota roots Whitessence Srl, Viterbo, Italy 2005-OCT PMID[21954959]
NPO15265 Paeonia rockii Species Paeoniaceae Eukaryota n.a. root n.a. PMID[21954959]
NPO15265 Paeonia rockii Species Paeoniaceae Eukaryota n.a. seed n.a. PMID[23497864]
NPO33150 Artocarpus communis Species Moraceae Eukaryota roots Khon Kaen, Thailand 2009-DEC PMID[25537111]
NPO33150 Artocarpus communis Species Moraceae Eukaryota n.a. n.a. n.a. PMID[26178912]
NPO15265 Paeonia rockii Species Paeoniaceae Eukaryota Seeds DingXi, GanSu, China early autumn (from August to the beginning of September PMID[32545196]
NPO15265 Paeonia rockii Species Paeoniaceae Eukaryota Seeds LanZhou, GanSu, China early autumn (from August to the beginning of September PMID[32545196]
NPO15265 Paeonia rockii Species Paeoniaceae Eukaryota Seeds Yangling, Shaanxi, China 70 days after pollination PMID[33131958]
NPO15265 Paeonia rockii Species Paeoniaceae Eukaryota Fruits Yangling, Shaanxi, China 10 days after pollination PMID[33131958]
NPO15265 Paeonia rockii Species Paeoniaceae Eukaryota Seeds Yangling, Shaanxi, China 80 days after pollination PMID[33131958]
NPO15265 Paeonia rockii Species Paeoniaceae Eukaryota Fruits Yangling, Shaanxi, China 20 days after pollination PMID[33131958]
NPO15265 Paeonia rockii Species Paeoniaceae Eukaryota Seeds Yangling, Shaanxi, China 90 days after pollination PMID[33131958]
NPO15265 Paeonia rockii Species Paeoniaceae Eukaryota Fruits Yangling, Shaanxi, China 30 days after pollination PMID[33131958]
NPO15265 Paeonia rockii Species Paeoniaceae Eukaryota Seeds Yangling, Shaanxi, China Maturation PMID[33131958]
NPO15265 Paeonia rockii Species Paeoniaceae Eukaryota Fruits Yangling, Shaanxi, China 40 days after pollination PMID[33131958]
NPO15265 Paeonia rockii Species Paeoniaceae Eukaryota Fruits Yangling, Shaanxi, China 50 days after pollination PMID[33131958]
NPO15265 Paeonia rockii Species Paeoniaceae Eukaryota Fruits Yangling, Shaanxi, China 60 days after pollination PMID[33131958]
NPO15265 Paeonia rockii Species Paeoniaceae Eukaryota Fruits Yangling, Shaanxi, China 70 days after pollination PMID[33131958]
NPO15265 Paeonia rockii Species Paeoniaceae Eukaryota Fruits Yangling, Shaanxi, China 80 days after pollination PMID[33131958]
NPO15265 Paeonia rockii Species Paeoniaceae Eukaryota Fruits Yangling, Shaanxi, China 90 days after pollination PMID[33131958]
NPO15265 Paeonia rockii Species Paeoniaceae Eukaryota Fruits Yangling, Shaanxi, China Maturation PMID[33131958]
NPO15265 Paeonia rockii Species Paeoniaceae Eukaryota Seeds Yangling, Shaanxi, China 10 days after pollination PMID[33131958]
NPO15265 Paeonia rockii Species Paeoniaceae Eukaryota Seeds Yangling, Shaanxi, China 20 days after pollination PMID[33131958]
NPO15265 Paeonia rockii Species Paeoniaceae Eukaryota Seeds Yangling, Shaanxi, China 30 days after pollination PMID[33131958]
NPO15265 Paeonia rockii Species Paeoniaceae Eukaryota Seeds Yangling, Shaanxi, China 40 days after pollination PMID[33131958]
NPO15265 Paeonia rockii Species Paeoniaceae Eukaryota Seeds Yangling, Shaanxi, China 50 days after pollination PMID[33131958]
NPO15265 Paeonia rockii Species Paeoniaceae Eukaryota Seeds Yangling, Shaanxi, China 60 days after pollination PMID[33131958]
NPO28969 Solanum sarrachoides Species Solanaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO28969 Solanum sarrachoides Species Solanaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO28969 Solanum sarrachoides Species Solanaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO28803 Artocarpus chama Species Moraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO29358 Senecio oxyodon Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO29318 Cereus validus Species Cactaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14058 Papaver pavoninum Species Papaveraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO29409 Oenothera laciniata Species Onagraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12131 Salvia calycina Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO29386 Agabus bipustulatus Species Dytiscidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO29156 Conyza incana Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15554 Eucalyptus amplifolia Species Myrtaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14309 Desmodium tortuosum Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14430 Grateloupia carnosa Species Halymeniaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7819.1 Epichloe festucae var. lolii Varieties Clavicipitaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15265 Paeonia rockii Species Paeoniaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28969 Solanum sarrachoides Species Solanaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO29519 Primula glaucescens Species Primulaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO29462 Helinus ovatus Species Rhamnaceae 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
NPT81 Cell Line A549 Homo sapiens ED50 = 8.5 ug ml-1 PMID[522563]
NPT83 Cell Line MCF7 Homo sapiens ED50 = 2.2 ug ml-1 PMID[522563]
NPT309 Cell Line 1A9 Homo sapiens ED50 < 1.25 ug ml-1 PMID[522563]
NPT180 Cell Line HCT-8 Homo sapiens ED50 = 3.3 ug ml-1 PMID[522563]
NPT308 Cell Line CAKI-1 Homo sapiens ED50 = 9.7 ug ml-1 PMID[522563]
NPT147 Cell Line SK-MEL-2 Homo sapiens ED50 = 4.3 ug ml-1 PMID[522563]
NPT306 Cell Line PC-3 Homo sapiens ED50 = 6.9 ug ml-1 PMID[522563]
NPT82 Cell Line MDA-MB-231 Homo sapiens ED50 = 3.0 ug ml-1 PMID[522563]
NPT91 Cell Line KB Homo sapiens ED50 = 6.5 ug ml-1 PMID[522563]
NPT196 Cell Line AGS Homo sapiens Activity = 58.4 % PMID[522564]
NPT196 Cell Line AGS Homo sapiens FC = 1.9 n.a. PMID[522564]
NPT196 Cell Line AGS Homo sapiens Inhibition = 3.6 % PMID[522564]
NPT196 Cell Line AGS Homo sapiens FC = 12.2 n.a. PMID[522564]
NPT196 Cell Line AGS Homo sapiens FC = 3.7 n.a. PMID[522564]
NPT196 Cell Line AGS Homo sapiens Inhibition = 2.9 % PMID[522564]
NPT196 Cell Line AGS Homo sapiens Inhibition = 32.7 % PMID[522564]
NPT196 Cell Line AGS Homo sapiens Activity = 44.0 % PMID[522564]
NPT196 Cell Line AGS Homo sapiens FC = 11.1 n.a. PMID[522564]
NPT196 Cell Line AGS Homo sapiens FC = 34.3 n.a. PMID[522564]
NPT168 Cell Line P388 Mus musculus IC50 = 140.0 nM PMID[522565]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. ED50 = 6.4 ug ml-1 PMID[522563]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. ED50 > 10.0 ug ml-1 PMID[522563]

☑ 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 NPC276444 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
0.9933 High Similarity NPC218871
0.9933 High Similarity NPC476630
0.9865 High Similarity NPC170492
0.9737 High Similarity NPC198829
0.9737 High Similarity NPC259456
0.9733 High Similarity NPC471985
0.9673 High Similarity NPC194427
0.9671 High Similarity NPC204290
0.9669 High Similarity NPC237418
0.9664 High Similarity NPC249570
0.9662 High Similarity NPC3825
0.9662 High Similarity NPC88804
0.9608 High Similarity NPC29876
0.9608 High Similarity NPC167678
0.9605 High Similarity NPC469658
0.9603 High Similarity NPC282307
0.9603 High Similarity NPC170026
0.96 High Similarity NPC476631
0.9597 High Similarity NPC154345
0.9548 High Similarity NPC156432
0.9545 High Similarity NPC329760
0.9545 High Similarity NPC472448
0.9545 High Similarity NPC83922
0.9545 High Similarity NPC261470
0.9542 High Similarity NPC476980
0.9533 High Similarity NPC157784
0.9533 High Similarity NPC37684
0.9533 High Similarity NPC63187
0.9484 High Similarity NPC189473
0.9484 High Similarity NPC23298
0.9484 High Similarity NPC207690
0.9477 High Similarity NPC184755
0.9477 High Similarity NPC74178
0.9474 High Similarity NPC191146
0.9474 High Similarity NPC68093
0.9467 High Similarity NPC304295
0.9467 High Similarity NPC205046
0.9467 High Similarity NPC59162
0.9423 High Similarity NPC130920
0.9423 High Similarity NPC85057
0.9423 High Similarity NPC239752
0.9423 High Similarity NPC50960
0.9423 High Similarity NPC472450
0.9423 High Similarity NPC275780
0.9419 High Similarity NPC78332
0.9416 High Similarity NPC28241
0.9416 High Similarity NPC119209
0.9416 High Similarity NPC118256
0.9416 High Similarity NPC192686
0.9416 High Similarity NPC476280
0.9412 High Similarity NPC78225
0.9412 High Similarity NPC218313
0.9412 High Similarity NPC471209
0.9412 High Similarity NPC476981
0.9412 High Similarity NPC474681
0.9408 High Similarity NPC472280
0.9408 High Similarity NPC113906
0.9408 High Similarity NPC133392
0.9408 High Similarity NPC234255
0.9404 High Similarity NPC471982
0.9404 High Similarity NPC237994
0.94 High Similarity NPC184136
0.9367 High Similarity NPC476637
0.9363 High Similarity NPC472449
0.9363 High Similarity NPC37870
0.9363 High Similarity NPC39091
0.9359 High Similarity NPC303460
0.9359 High Similarity NPC306321
0.9355 High Similarity NPC258331
0.9355 High Similarity NPC278427
0.9355 High Similarity NPC40037
0.9355 High Similarity NPC474038
0.9351 High Similarity NPC204879
0.9351 High Similarity NPC46736
0.9351 High Similarity NPC197856
0.9351 High Similarity NPC172770
0.9351 High Similarity NPC185258
0.9346 High Similarity NPC138243
0.9346 High Similarity NPC142339
0.9346 High Similarity NPC3980
0.9346 High Similarity NPC472455
0.9346 High Similarity NPC133970
0.9346 High Similarity NPC6633
0.9346 High Similarity NPC5322
0.9342 High Similarity NPC231018
0.9342 High Similarity NPC176775
0.9342 High Similarity NPC74924
0.9342 High Similarity NPC69394
0.9342 High Similarity NPC47781
0.9342 High Similarity NPC22519
0.9342 High Similarity NPC160951
0.9342 High Similarity NPC255350
0.9342 High Similarity NPC145379
0.9342 High Similarity NPC213896
0.9342 High Similarity NPC274327
0.9342 High Similarity NPC192083
0.9342 High Similarity NPC183878
0.9329 High Similarity NPC108406
0.9329 High Similarity NPC130230
0.9329 High Similarity NPC275772
0.9329 High Similarity NPC239312
0.9308 High Similarity NPC101107
0.9299 High Similarity NPC259757
0.9295 High Similarity NPC474162
0.9295 High Similarity NPC25152
0.9295 High Similarity NPC206605
0.9295 High Similarity NPC229632
0.9295 High Similarity NPC474150
0.9295 High Similarity NPC8300
0.929 High Similarity NPC235018
0.929 High Similarity NPC80375
0.929 High Similarity NPC45146
0.929 High Similarity NPC471973
0.929 High Similarity NPC297212
0.929 High Similarity NPC475784
0.929 High Similarity NPC139036
0.929 High Similarity NPC246478
0.929 High Similarity NPC328102
0.9286 High Similarity NPC284820
0.9286 High Similarity NPC27337
0.9286 High Similarity NPC473272
0.9286 High Similarity NPC223787
0.9286 High Similarity NPC273843
0.9286 High Similarity NPC36852
0.9286 High Similarity NPC79053
0.9286 High Similarity NPC262286
0.9286 High Similarity NPC52889
0.9286 High Similarity NPC236796
0.9281 High Similarity NPC200246
0.9281 High Similarity NPC146165
0.9281 High Similarity NPC163780
0.9281 High Similarity NPC138360
0.9281 High Similarity NPC321779
0.9281 High Similarity NPC280339
0.9281 High Similarity NPC213622
0.9281 High Similarity NPC256612
0.9281 High Similarity NPC201136
0.9281 High Similarity NPC196439
0.9281 High Similarity NPC2476
0.9281 High Similarity NPC92659
0.9281 High Similarity NPC167815
0.9281 High Similarity NPC128863
0.9281 High Similarity NPC4455
0.9281 High Similarity NPC50715
0.9281 High Similarity NPC20830
0.9281 High Similarity NPC227325
0.9281 High Similarity NPC183597
0.9276 High Similarity NPC71334
0.9276 High Similarity NPC83508
0.9276 High Similarity NPC100887
0.9276 High Similarity NPC275836
0.9276 High Similarity NPC301323
0.9276 High Similarity NPC25270
0.9276 High Similarity NPC239128
0.9276 High Similarity NPC156222
0.9276 High Similarity NPC131624
0.9276 High Similarity NPC57030
0.9276 High Similarity NPC198826
0.9276 High Similarity NPC188203
0.9276 High Similarity NPC293183
0.9276 High Similarity NPC256283
0.9276 High Similarity NPC187498
0.9276 High Similarity NPC162313
0.9276 High Similarity NPC241498
0.9276 High Similarity NPC106976
0.9276 High Similarity NPC275722
0.9276 High Similarity NPC120163
0.9276 High Similarity NPC222830
0.9276 High Similarity NPC212678
0.9272 High Similarity NPC120105
0.9272 High Similarity NPC62042
0.9272 High Similarity NPC101957
0.9267 High Similarity NPC276930
0.9267 High Similarity NPC12367
0.9267 High Similarity NPC118726
0.9257 High Similarity NPC279121
0.9245 High Similarity NPC475805
0.9245 High Similarity NPC471287
0.9236 High Similarity NPC12461
0.9236 High Similarity NPC236521
0.9236 High Similarity NPC472625
0.9236 High Similarity NPC234004
0.9236 High Similarity NPC186686
0.9236 High Similarity NPC248638
0.9236 High Similarity NPC152659
0.9231 High Similarity NPC26326
0.9231 High Similarity NPC266314
0.9231 High Similarity NPC471210
0.9231 High Similarity NPC234644
0.9231 High Similarity NPC472632
0.9231 High Similarity NPC472275
0.9231 High Similarity NPC32694
0.9231 High Similarity NPC61010
0.9226 High Similarity NPC100123
0.9226 High Similarity NPC474290
0.9226 High Similarity NPC53545
0.9226 High Similarity NPC117418
0.9226 High Similarity NPC250214
0.9226 High Similarity NPC280680
0.9226 High Similarity NPC95936

  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 NPC276444 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
0.9342 High Similarity NPD2393 Clinical (unspecified phase)
0.9342 High Similarity NPD2801 Approved
0.9257 High Similarity NPD1511 Approved
0.9133 High Similarity NPD1512 Approved
0.9026 High Similarity NPD1934 Approved
0.894 High Similarity NPD4378 Clinical (unspecified phase)
0.8816 High Similarity NPD7410 Clinical (unspecified phase)
0.8704 High Similarity NPD6167 Clinical (unspecified phase)
0.8704 High Similarity NPD6168 Clinical (unspecified phase)
0.8704 High Similarity NPD6166 Phase 2
0.8654 High Similarity NPD4380 Phase 2
0.8616 High Similarity NPD3882 Suspended
0.8571 High Similarity NPD5494 Approved
0.8553 High Similarity NPD3817 Phase 2
0.8545 High Similarity NPD7054 Approved
0.8494 Intermediate Similarity NPD7074 Phase 3
0.8494 Intermediate Similarity NPD7472 Approved
0.8485 Intermediate Similarity NPD3818 Discontinued
0.8452 Intermediate Similarity NPD4338 Clinical (unspecified phase)
0.8443 Intermediate Similarity NPD6797 Phase 2
0.8393 Intermediate Similarity NPD7251 Discontinued
0.8385 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.8355 Intermediate Similarity NPD1552 Clinical (unspecified phase)
0.8355 Intermediate Similarity NPD1550 Clinical (unspecified phase)
0.8344 Intermediate Similarity NPD1510 Phase 2
0.8333 Intermediate Similarity NPD4381 Clinical (unspecified phase)
0.8333 Intermediate Similarity NPD7075 Discontinued
0.8323 Intermediate Similarity NPD8443 Clinical (unspecified phase)
0.8301 Intermediate Similarity NPD1549 Phase 2
0.8289 Intermediate Similarity NPD2796 Approved
0.8261 Intermediate Similarity NPD7096 Clinical (unspecified phase)
0.8261 Intermediate Similarity NPD7819 Suspended
0.825 Intermediate Similarity NPD7411 Suspended
0.8242 Intermediate Similarity NPD6232 Discontinued
0.8235 Intermediate Similarity NPD7808 Phase 3
0.8214 Intermediate Similarity NPD5844 Phase 1
0.8214 Intermediate Similarity NPD7804 Clinical (unspecified phase)
0.821 Intermediate Similarity NPD5402 Approved
0.8204 Intermediate Similarity NPD7473 Discontinued
0.82 Intermediate Similarity NPD1240 Approved
0.82 Intermediate Similarity NPD943 Approved
0.8199 Intermediate Similarity NPD6801 Discontinued
0.8182 Intermediate Similarity NPD6959 Discontinued
0.817 Intermediate Similarity NPD2935 Discontinued
0.8092 Intermediate Similarity NPD1607 Approved
0.8077 Intermediate Similarity NPD3750 Approved
0.8072 Intermediate Similarity NPD1247 Approved
0.8038 Intermediate Similarity NPD6799 Approved
0.8037 Intermediate Similarity NPD1465 Phase 2
0.8013 Intermediate Similarity NPD2800 Approved
0.7949 Intermediate Similarity NPD970 Clinical (unspecified phase)
0.7939 Intermediate Similarity NPD7768 Phase 2
0.7933 Intermediate Similarity NPD1529 Clinical (unspecified phase)
0.7929 Intermediate Similarity NPD7852 Clinical (unspecified phase)
0.7907 Intermediate Similarity NPD7993 Clinical (unspecified phase)
0.7892 Intermediate Similarity NPD3749 Approved
0.7888 Intermediate Similarity NPD5403 Approved
0.7867 Intermediate Similarity NPD1530 Clinical (unspecified phase)
0.7861 Intermediate Similarity NPD6559 Discontinued
0.7853 Intermediate Similarity NPD6599 Discontinued
0.7844 Intermediate Similarity NPD919 Approved
0.7785 Intermediate Similarity NPD1243 Approved
0.7785 Intermediate Similarity NPD7421 Clinical (unspecified phase)
0.7764 Intermediate Similarity NPD2534 Approved
0.7764 Intermediate Similarity NPD2532 Approved
0.7764 Intermediate Similarity NPD5401 Approved
0.7764 Intermediate Similarity NPD2533 Approved
0.7756 Intermediate Similarity NPD3748 Approved
0.7727 Intermediate Similarity NPD1613 Approved
0.7727 Intermediate Similarity NPD1612 Clinical (unspecified phase)
0.7712 Intermediate Similarity NPD2313 Discontinued
0.7707 Intermediate Similarity NPD6100 Approved
0.7707 Intermediate Similarity NPD6099 Approved
0.7702 Intermediate Similarity NPD7390 Discontinued
0.7683 Intermediate Similarity NPD3226 Approved
0.7677 Intermediate Similarity NPD230 Phase 1
0.7669 Intermediate Similarity NPD920 Approved
0.7661 Intermediate Similarity NPD3926 Phase 2
0.7654 Intermediate Similarity NPD8397 Clinical (unspecified phase)
0.7643 Intermediate Similarity NPD1509 Clinical (unspecified phase)
0.7643 Intermediate Similarity NPD2799 Discontinued
0.7643 Intermediate Similarity NPD651 Clinical (unspecified phase)
0.7628 Intermediate Similarity NPD6651 Approved
0.7614 Intermediate Similarity NPD4419 Clinical (unspecified phase)
0.7597 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.7595 Intermediate Similarity NPD1551 Phase 2
0.7569 Intermediate Similarity NPD7879 Clinical (unspecified phase)
0.7564 Intermediate Similarity NPD447 Suspended
0.7561 Intermediate Similarity NPD6980 Clinical (unspecified phase)
0.7547 Intermediate Similarity NPD2346 Discontinued
0.7547 Intermediate Similarity NPD2344 Approved
0.7546 Intermediate Similarity NPD642 Clinical (unspecified phase)
0.7532 Intermediate Similarity NPD3027 Phase 3
0.7531 Intermediate Similarity NPD643 Clinical (unspecified phase)
0.7516 Intermediate Similarity NPD6398 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD5953 Discontinued
0.7486 Intermediate Similarity NPD7286 Phase 2
0.7484 Intermediate Similarity NPD4907 Clinical (unspecified phase)
0.7429 Intermediate Similarity NPD3751 Discontinued
0.7419 Intermediate Similarity NPD4625 Phase 3
0.741 Intermediate Similarity NPD1653 Approved
0.7407 Intermediate Similarity NPD1878 Clinical (unspecified phase)
0.7407 Intermediate Similarity NPD4628 Phase 3
0.7399 Intermediate Similarity NPD3787 Discontinued
0.7391 Intermediate Similarity NPD4360 Phase 2
0.7391 Intermediate Similarity NPD4363 Phase 3
0.7389 Intermediate Similarity NPD8055 Clinical (unspecified phase)
0.7386 Intermediate Similarity NPD1203 Approved
0.738 Intermediate Similarity NPD7501 Clinical (unspecified phase)
0.7378 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.7372 Intermediate Similarity NPD3268 Approved
0.7362 Intermediate Similarity NPD6190 Approved
0.7362 Intermediate Similarity NPD2309 Approved
0.7355 Intermediate Similarity NPD4908 Phase 1
0.7342 Intermediate Similarity NPD5123 Clinical (unspecified phase)
0.7342 Intermediate Similarity NPD5124 Phase 1
0.7341 Intermediate Similarity NPD7199 Phase 2
0.7338 Intermediate Similarity NPD2798 Approved
0.7333 Intermediate Similarity NPD7422 Clinical (unspecified phase)
0.7326 Intermediate Similarity NPD6234 Discontinued
0.732 Intermediate Similarity NPD3225 Approved
0.7312 Intermediate Similarity NPD8090 Clinical (unspecified phase)
0.7312 Intermediate Similarity NPD4308 Phase 3
0.7312 Intermediate Similarity NPD7033 Discontinued
0.7287 Intermediate Similarity NPD6779 Approved
0.7287 Intermediate Similarity NPD6780 Approved
0.7287 Intermediate Similarity NPD6778 Approved
0.7287 Intermediate Similarity NPD6776 Approved
0.7287 Intermediate Similarity NPD6777 Approved
0.7287 Intermediate Similarity NPD6781 Approved
0.7287 Intermediate Similarity NPD6782 Approved
0.7273 Intermediate Similarity NPD2797 Approved
0.7257 Intermediate Similarity NPD7184 Clinical (unspecified phase)
0.7255 Intermediate Similarity NPD4379 Clinical (unspecified phase)
0.724 Intermediate Similarity NPD7584 Approved
0.7237 Intermediate Similarity NPD422 Phase 1
0.7235 Intermediate Similarity NPD6844 Discontinued
0.7233 Intermediate Similarity NPD1933 Approved
0.72 Intermediate Similarity NPD1548 Phase 1
0.72 Intermediate Similarity NPD5711 Approved
0.72 Intermediate Similarity NPD5710 Approved
0.719 Intermediate Similarity NPD9717 Approved
0.719 Intermediate Similarity NPD9269 Phase 2
0.719 Intermediate Similarity NPD1608 Approved
0.7182 Intermediate Similarity NPD8313 Approved
0.7182 Intermediate Similarity NPD8312 Approved
0.7179 Intermediate Similarity NPD9494 Approved
0.7173 Intermediate Similarity NPD7435 Discontinued
0.7167 Intermediate Similarity NPD7685 Pre-registration
0.7166 Intermediate Similarity NPD4362 Clinical (unspecified phase)
0.7166 Intermediate Similarity NPD4361 Phase 2
0.716 Intermediate Similarity NPD5405 Approved
0.716 Intermediate Similarity NPD5406 Approved
0.716 Intermediate Similarity NPD5404 Approved
0.716 Intermediate Similarity NPD5408 Approved
0.7158 Intermediate Similarity NPD8434 Phase 2
0.7158 Intermediate Similarity NPD8150 Discontinued
0.7151 Intermediate Similarity NPD4288 Approved
0.7143 Intermediate Similarity NPD4749 Approved
0.7135 Intermediate Similarity NPD7228 Approved
0.7135 Intermediate Similarity NPD37 Approved
0.7134 Intermediate Similarity NPD6832 Phase 2
0.7126 Intermediate Similarity NPD7004 Clinical (unspecified phase)
0.7125 Intermediate Similarity NPD1899 Clinical (unspecified phase)
0.7124 Intermediate Similarity NPD1201 Approved
0.7124 Intermediate Similarity NPD1610 Phase 2
0.7124 Intermediate Similarity NPD1547 Clinical (unspecified phase)
0.711 Intermediate Similarity NPD4965 Approved
0.711 Intermediate Similarity NPD4966 Approved
0.711 Intermediate Similarity NPD4967 Phase 2
0.7108 Intermediate Similarity NPD3300 Phase 2
0.7102 Intermediate Similarity NPD7229 Phase 3
0.7092 Intermediate Similarity NPD7783 Phase 2
0.7092 Intermediate Similarity NPD7782 Clinical (unspecified phase)
0.7083 Intermediate Similarity NPD7697 Approved
0.7083 Intermediate Similarity NPD7696 Phase 3
0.7083 Intermediate Similarity NPD7698 Approved
0.7076 Intermediate Similarity NPD7615 Clinical (unspecified phase)
0.707 Intermediate Similarity NPD2861 Phase 2
0.7063 Intermediate Similarity NPD4307 Phase 2
0.7059 Intermediate Similarity NPD7458 Discontinued
0.7059 Intermediate Similarity NPD5808 Clinical (unspecified phase)
0.7051 Intermediate Similarity NPD3267 Approved
0.7051 Intermediate Similarity NPD1470 Approved
0.7051 Intermediate Similarity NPD3266 Approved
0.7047 Intermediate Similarity NPD7871 Phase 2
0.7047 Intermediate Similarity NPD7870 Phase 2
0.7044 Intermediate Similarity NPD411 Approved
0.7033 Intermediate Similarity NPD7549 Discontinued
0.7031 Intermediate Similarity NPD6823 Phase 2
0.703 Intermediate Similarity NPD2654 Approved
0.7026 Intermediate Similarity NPD7701 Phase 2
0.7022 Intermediate Similarity NPD2403 Approved
0.7021 Intermediate Similarity NPD6534 Approved
0.7021 Intermediate Similarity NPD6535 Approved
0.7018 Intermediate Similarity NPD6585 Discontinued
0.7 Intermediate Similarity NPD6671 Approved
0.7 Intermediate Similarity NPD6233 Phase 2
0.6993 Remote Similarity NPD17 Approved
0.699 Remote Similarity NPD8151 Discontinued

  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