Structure

Physi-Chem Properties

Molecular Weight:  168.08
Volume:  174.125
LogP:  0.999
LogD:  1.133
LogS:  -1.834
# Rotatable Bonds:  4
TPSA:  50.44
# H-Bond Aceptor:  3
# H-Bond Donor:  1
# Rings:  1
# Heavy Atoms:  3

MedChem Properties

QED Drug-Likeness Score:  0.695
Synthetic Accessibility Score:  2.974
Fsp3:  0.444
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Accepted
BMS Rule:  0
Golden Triangle Rule:  Rejected
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.408
MDCK Permeability:  2.272108758916147e-05
Pgp-inhibitor:  0.002
Pgp-substrate:  0.192
Human Intestinal Absorption (HIA):  0.013
20% Bioavailability (F20%):  0.003
30% Bioavailability (F30%):  0.066

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.93
Plasma Protein Binding (PPB):  63.45048141479492%
Volume Distribution (VD):  1.336
Pgp-substrate:  51.892417907714844%

ADMET: Metabolism

CYP1A2-inhibitor:  0.485
CYP1A2-substrate:  0.119
CYP2C19-inhibitor:  0.219
CYP2C19-substrate:  0.063
CYP2C9-inhibitor:  0.078
CYP2C9-substrate:  0.133
CYP2D6-inhibitor:  0.01
CYP2D6-substrate:  0.388
CYP3A4-inhibitor:  0.012
CYP3A4-substrate:  0.206

ADMET: Excretion

Clearance (CL):  11.707
Half-life (T1/2):  0.892

ADMET: Toxicity

hERG Blockers:  0.025
Human Hepatotoxicity (H-HT):  0.143
Drug-inuced Liver Injury (DILI):  0.184
AMES Toxicity:  0.024
Rat Oral Acute Toxicity:  0.759
Maximum Recommended Daily Dose:  0.257
Skin Sensitization:  0.063
Carcinogencity:  0.94
Eye Corrosion:  0.115
Eye Irritation:  0.947
Respiratory Toxicity:  0.973

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Structure MOL file  
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Biological Activities  
Similar NPs/Drugs  

  Natural Product: NPC79557

Natural Product ID:  NPC79557
Common Name*:   (4S)-1-(Furan-3-Yl)-4-Hydroxypentan-1-One
IUPAC Name:   (4S)-1-(furan-3-yl)-4-hydroxypentan-1-one
Synonyms:  
Standard InCHIKey:  RJYQLMILDVERHH-ZETCQYMHSA-N
Standard InCHI:  InChI=1S/C9H12O3/c1-7(10)2-3-9(11)8-4-5-12-6-8/h4-7,10H,2-3H2,1H3/t7-/m0/s1
SMILES:  C[C@@H](CCC(=O)c1cocc1)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL1965801
PubChem CID:   6711829
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0004603] Organic oxygen compounds
      • [CHEMONTID:0000323] Organooxygen compounds
        • [CHEMONTID:0001831] Carbonyl compounds
          • [CHEMONTID:0000118] Ketones
            • [CHEMONTID:0003670] Aryl ketones
              • [CHEMONTID:0003671] Aryl alkyl ketones

*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
NPO4619 Artemisia gilvescens Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[12713410]
NPO6495 Datura stramonium Species Solanaceae Eukaryota n.a. n.a. n.a. PMID[15374592]
NPO598 Oenanthe fistulosa Species Apiaceae Eukaryota n.a. n.a. n.a. PMID[19245244]
NPO6495 Datura stramonium Species Solanaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO6495 Datura stramonium Species Solanaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO6495 Datura stramonium Species Solanaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO6495 Datura stramonium Species Solanaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO5542 Ceratocystis fimbriata Species Ceratocystidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4619 Artemisia gilvescens Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO920 Cheilanthes chusana Species Pteridaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2760 Picris evae Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1839 Bryophyllum calycinum Species Spathidiidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6495 Datura stramonium Species Solanaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO598 Oenanthe fistulosa Species Apiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

  NP Quantity Composition/Concentration

Organism ID NP ID Organism Material Preparation Organism Part NP Quantity (Standard) NP Quantity (Minimum) NP Quantity (Maximum) Quantity Unit Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT368 Cell Line SN12C Homo sapiens GI50 n.a. 100000.0 nM PMID[483142]
NPT370 Cell Line NCI-H23 Homo sapiens GI50 n.a. 100000.0 nM PMID[483142]
NPT369 Cell Line ACHN Homo sapiens GI50 n.a. 100000.0 nM PMID[483142]
NPT371 Cell Line UO-31 Homo sapiens GI50 n.a. 100000.0 nM PMID[483142]
NPT372 Cell Line HOP-92 Homo sapiens GI50 n.a. 100000.0 nM PMID[483142]
NPT116 Cell Line HL-60 Homo sapiens GI50 n.a. 100000.0 nM PMID[483142]
NPT373 Cell Line SK-MEL-5 Homo sapiens GI50 n.a. 100000.0 nM PMID[483142]
NPT374 Cell Line SF-539 Homo sapiens GI50 n.a. 100000.0 nM PMID[483142]
NPT375 Cell Line Malme-3M Homo sapiens GI50 n.a. 100000.0 nM PMID[483142]
NPT376 Cell Line A498 Homo sapiens GI50 n.a. 100000.0 nM PMID[483142]
NPT111 Cell Line K562 Homo sapiens GI50 n.a. 100000.0 nM PMID[483142]
NPT377 Cell Line OVCAR-3 Homo sapiens GI50 n.a. 100000.0 nM PMID[483142]
NPT112 Cell Line MOLT-4 Homo sapiens GI50 n.a. 100000.0 nM PMID[483142]
NPT379 Cell Line HOP-62 Homo sapiens GI50 n.a. 100000.0 nM PMID[483142]
NPT380 Cell Line U-251 Homo sapiens GI50 n.a. 100000.0 nM PMID[483142]
NPT381 Cell Line OVCAR-8 Homo sapiens GI50 n.a. 100000.0 nM PMID[483142]
NPT382 Cell Line OVCAR-5 Homo sapiens GI50 n.a. 100000.0 nM PMID[483142]
NPT572 Cell Line DMS-273 Homo sapiens GI50 n.a. 100000.0 nM PMID[483142]
NPT383 Cell Line SNB-19 Homo sapiens GI50 n.a. 100000.0 nM PMID[483142]
NPT384 Cell Line TK-10 Homo sapiens GI50 n.a. 100000.0 nM PMID[483142]
NPT385 Cell Line SR Homo sapiens GI50 n.a. 100000.0 nM PMID[483142]
NPT573 Cell Line M19-MEL Homo sapiens GI50 n.a. 100000.0 nM PMID[483142]
NPT323 Cell Line SW-620 Homo sapiens GI50 n.a. 100000.0 nM PMID[483142]
NPT386 Cell Line KM12 Homo sapiens GI50 n.a. 100000.0 nM PMID[483142]
NPT455 Cell Line NCI-H522 Homo sapiens GI50 n.a. 100000.0 nM PMID[483142]
NPT574 Cell Line XF498 Homo sapiens GI50 n.a. 100000.0 nM PMID[483142]
NPT387 Cell Line M14 Homo sapiens GI50 n.a. 100000.0 nM PMID[483142]
NPT388 Cell Line NCI-H322M Homo sapiens GI50 n.a. 100000.0 nM PMID[483142]
NPT389 Cell Line RPMI-8226 Homo sapiens GI50 n.a. 100000.0 nM PMID[483142]
NPT456 Cell Line OVCAR-4 Homo sapiens GI50 n.a. 100000.0 nM PMID[483142]
NPT390 Cell Line LOX IMVI Homo sapiens GI50 n.a. 100000.0 nM PMID[483142]
NPT575 Cell Line KM-20L2 Homo sapiens GI50 n.a. 100000.0 nM PMID[483142]
NPT147 Cell Line SK-MEL-2 Homo sapiens GI50 n.a. 100000.0 nM PMID[483142]
NPT391 Cell Line HCC 2998 Homo sapiens GI50 n.a. 66069.34 nM PMID[483142]
NPT81 Cell Line A549 Homo sapiens GI50 n.a. 100000.0 nM PMID[483142]
NPT392 Cell Line SNB-75 Homo sapiens GI50 n.a. 34514.37 nM PMID[483142]
NPT148 Cell Line HCT-15 Homo sapiens GI50 n.a. 100000.0 nM PMID[483142]
NPT393 Cell Line HCT-116 Homo sapiens GI50 n.a. 100000.0 nM PMID[483142]
NPT394 Cell Line EKVX Homo sapiens GI50 n.a. 100000.0 nM PMID[483142]
NPT395 Cell Line SF-268 Homo sapiens GI50 n.a. 100000.0 nM PMID[483142]
NPT146 Cell Line SK-OV-3 Homo sapiens GI50 n.a. 100000.0 nM PMID[483142]
NPT731 Cell Line LXFL 529 Homo sapiens GI50 n.a. 100000.0 nM PMID[483142]
NPT576 Cell Line DMS-114 Homo sapiens GI50 n.a. 100000.0 nM PMID[483142]
NPT397 Cell Line NCI-H460 Homo sapiens GI50 n.a. 100000.0 nM PMID[483142]
NPT308 Cell Line CAKI-1 Homo sapiens GI50 n.a. 100000.0 nM PMID[483142]
NPT398 Cell Line UACC-62 Homo sapiens GI50 n.a. 100000.0 nM PMID[483142]
NPT399 Cell Line SF-295 Homo sapiens GI50 n.a. 100000.0 nM PMID[483142]
NPT458 Cell Line IGROV-1 Homo sapiens GI50 n.a. 100000.0 nM PMID[483142]
NPT401 Cell Line 786-0 Homo sapiens GI50 n.a. 100000.0 nM PMID[483142]
NPT577 Cell Line RXF 631 Homo sapiens GI50 n.a. 100000.0 nM PMID[483142]
NPT403 Cell Line UACC-257 Homo sapiens GI50 n.a. 100000.0 nM PMID[483142]
NPT578 Cell Line SNB-78 Homo sapiens GI50 n.a. 100000.0 nM PMID[483142]
NPT579 Cell Line DLD-1 Homo sapiens GI50 n.a. 100000.0 nM PMID[483142]
NPT404 Cell Line CCRF-CEM Homo sapiens GI50 n.a. 100000.0 nM PMID[483142]
NPT139 Cell Line HT-29 Homo sapiens GI50 n.a. 100000.0 nM PMID[483142]
NPT405 Cell Line NCI-H226 Homo sapiens GI50 n.a. 100000.0 nM PMID[483142]
NPT170 Cell Line SK-MEL-28 Homo sapiens GI50 n.a. 100000.0 nM PMID[483142]
NPT406 Cell Line RXF 393 Homo sapiens GI50 n.a. 100000.0 nM PMID[483142]
NPT407 Cell Line COLO 205 Homo sapiens GI50 n.a. 100000.0 nM PMID[483142]
NPT732 Cell Line HOP-18 Homo sapiens GI50 n.a. 74989.42 nM PMID[483142]

☑ 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 NPC79557 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
0.9386 High Similarity NPC45536
0.876 High Similarity NPC263870
0.8596 High Similarity NPC140688
0.85 High Similarity NPC208906
0.85 High Similarity NPC144745
0.8487 Intermediate Similarity NPC28054
0.8468 Intermediate Similarity NPC118853
0.8455 Intermediate Similarity NPC473379
0.8455 Intermediate Similarity NPC471549
0.8448 Intermediate Similarity NPC177331
0.8433 Intermediate Similarity NPC52412
0.84 Intermediate Similarity NPC474829
0.8385 Intermediate Similarity NPC106247
0.8333 Intermediate Similarity NPC473268
0.8321 Intermediate Similarity NPC159786
0.8308 Intermediate Similarity NPC474425
0.8308 Intermediate Similarity NPC474426
0.8308 Intermediate Similarity NPC470740
0.8308 Intermediate Similarity NPC474407
0.8306 Intermediate Similarity NPC477967
0.8279 Intermediate Similarity NPC243704
0.8271 Intermediate Similarity NPC472376
0.8268 Intermediate Similarity NPC474830
0.8268 Intermediate Similarity NPC319140
0.8268 Intermediate Similarity NPC95567
0.8268 Intermediate Similarity NPC476016
0.8258 Intermediate Similarity NPC146872
0.8231 Intermediate Similarity NPC473982
0.8226 Intermediate Similarity NPC1848
0.8217 Intermediate Similarity NPC21460
0.8195 Intermediate Similarity NPC186626
0.8189 Intermediate Similarity NPC474260
0.8189 Intermediate Similarity NPC329922
0.8189 Intermediate Similarity NPC329694
0.8189 Intermediate Similarity NPC23086
0.8189 Intermediate Similarity NPC81912
0.8182 Intermediate Similarity NPC150895
0.8175 Intermediate Similarity NPC243269
0.8154 Intermediate Similarity NPC136340
0.8154 Intermediate Similarity NPC17681
0.8154 Intermediate Similarity NPC61788
0.8134 Intermediate Similarity NPC236532
0.8125 Intermediate Similarity NPC471554
0.8125 Intermediate Similarity NPC473355
0.8125 Intermediate Similarity NPC471573
0.8125 Intermediate Similarity NPC184391
0.8125 Intermediate Similarity NPC471501
0.811 Intermediate Similarity NPC471559
0.8092 Intermediate Similarity NPC471544
0.8092 Intermediate Similarity NPC471545
0.8092 Intermediate Similarity NPC45358
0.8092 Intermediate Similarity NPC473344
0.8092 Intermediate Similarity NPC97740
0.8083 Intermediate Similarity NPC26157
0.8083 Intermediate Similarity NPC1811
0.8065 Intermediate Similarity NPC473969
0.8062 Intermediate Similarity NPC474279
0.8062 Intermediate Similarity NPC474438
0.806 Intermediate Similarity NPC42400
0.8047 Intermediate Similarity NPC46536
0.8047 Intermediate Similarity NPC138139
0.8045 Intermediate Similarity NPC158525
0.8033 Intermediate Similarity NPC205523
0.8031 Intermediate Similarity NPC188377
0.8031 Intermediate Similarity NPC65735
0.803 Intermediate Similarity NPC218838
0.8016 Intermediate Similarity NPC174915
0.8016 Intermediate Similarity NPC270807
0.8 Intermediate Similarity NPC105249
0.7985 Intermediate Similarity NPC46896
0.7984 Intermediate Similarity NPC21831
0.7984 Intermediate Similarity NPC187547
0.7984 Intermediate Similarity NPC83178
0.7971 Intermediate Similarity NPC267632
0.7971 Intermediate Similarity NPC254198
0.7969 Intermediate Similarity NPC75557
0.7969 Intermediate Similarity NPC71274
0.7956 Intermediate Similarity NPC205765
0.7953 Intermediate Similarity NPC475818
0.7939 Intermediate Similarity NPC45947
0.7923 Intermediate Similarity NPC207294
0.7923 Intermediate Similarity NPC329707
0.7923 Intermediate Similarity NPC112706
0.791 Intermediate Similarity NPC476947
0.7903 Intermediate Similarity NPC131801
0.7903 Intermediate Similarity NPC217180
0.7903 Intermediate Similarity NPC312525
0.7899 Intermediate Similarity NPC473152
0.7899 Intermediate Similarity NPC471521
0.7899 Intermediate Similarity NPC473356
0.7883 Intermediate Similarity NPC18904
0.7881 Intermediate Similarity NPC42471
0.7879 Intermediate Similarity NPC89133
0.7857 Intermediate Similarity NPC474817
0.7846 Intermediate Similarity NPC290955
0.7846 Intermediate Similarity NPC137570
0.7846 Intermediate Similarity NPC141059
0.7842 Intermediate Similarity NPC476946
0.7836 Intermediate Similarity NPC200718
0.7829 Intermediate Similarity NPC473885
0.7829 Intermediate Similarity NPC471074
0.7823 Intermediate Similarity NPC474987
0.7812 Intermediate Similarity NPC476351
0.7812 Intermediate Similarity NPC16922
0.781 Intermediate Similarity NPC90953
0.7803 Intermediate Similarity NPC939
0.7801 Intermediate Similarity NPC104924
0.7795 Intermediate Similarity NPC115859
0.7787 Intermediate Similarity NPC22678
0.7786 Intermediate Similarity NPC476944
0.7786 Intermediate Similarity NPC137295
0.7778 Intermediate Similarity NPC137710
0.7778 Intermediate Similarity NPC67345
0.7778 Intermediate Similarity NPC244862
0.7778 Intermediate Similarity NPC92941
0.7769 Intermediate Similarity NPC83301
0.7769 Intermediate Similarity NPC216810
0.7761 Intermediate Similarity NPC214097
0.7754 Intermediate Similarity NPC201370
0.7754 Intermediate Similarity NPC90296
0.7754 Intermediate Similarity NPC473983
0.7752 Intermediate Similarity NPC477038
0.7752 Intermediate Similarity NPC477965
0.7746 Intermediate Similarity NPC308799
0.7744 Intermediate Similarity NPC477645
0.7744 Intermediate Similarity NPC298190
0.7742 Intermediate Similarity NPC11821
0.7737 Intermediate Similarity NPC220094
0.7737 Intermediate Similarity NPC476943
0.7734 Intermediate Similarity NPC283284
0.7734 Intermediate Similarity NPC289911
0.7734 Intermediate Similarity NPC323118
0.7734 Intermediate Similarity NPC317217
0.773 Intermediate Similarity NPC185456
0.7724 Intermediate Similarity NPC474219
0.7724 Intermediate Similarity NPC474378
0.7714 Intermediate Similarity NPC243577
0.7714 Intermediate Similarity NPC103134
0.771 Intermediate Similarity NPC246392
0.7698 Intermediate Similarity NPC206007
0.7692 Intermediate Similarity NPC179354
0.7692 Intermediate Similarity NPC61284
0.7692 Intermediate Similarity NPC113428
0.7687 Intermediate Similarity NPC471817
0.7681 Intermediate Similarity NPC98395
0.7681 Intermediate Similarity NPC474615
0.7681 Intermediate Similarity NPC107571
0.768 Intermediate Similarity NPC76844
0.768 Intermediate Similarity NPC79202
0.768 Intermediate Similarity NPC59035
0.7674 Intermediate Similarity NPC272899
0.7664 Intermediate Similarity NPC310830
0.7664 Intermediate Similarity NPC470742
0.7656 Intermediate Similarity NPC474136
0.7652 Intermediate Similarity NPC477040
0.7652 Intermediate Similarity NPC279877
0.7652 Intermediate Similarity NPC26532
0.7652 Intermediate Similarity NPC477123
0.7652 Intermediate Similarity NPC477966
0.7652 Intermediate Similarity NPC477039
0.7647 Intermediate Similarity NPC265793
0.7634 Intermediate Similarity NPC74612
0.763 Intermediate Similarity NPC471006
0.7626 Intermediate Similarity NPC67003
0.7622 Intermediate Similarity NPC476938
0.7622 Intermediate Similarity NPC476937
0.7622 Intermediate Similarity NPC250228
0.7622 Intermediate Similarity NPC10088
0.7619 Intermediate Similarity NPC42458
0.7619 Intermediate Similarity NPC179170
0.7619 Intermediate Similarity NPC158261
0.7619 Intermediate Similarity NPC227660
0.7615 Intermediate Similarity NPC141252
0.7615 Intermediate Similarity NPC11799
0.7612 Intermediate Similarity NPC475092
0.7609 Intermediate Similarity NPC177262
0.7606 Intermediate Similarity NPC195920
0.7603 Intermediate Similarity NPC471613
0.7603 Intermediate Similarity NPC156244
0.7603 Intermediate Similarity NPC145830
0.7597 Intermediate Similarity NPC314329
0.7594 Intermediate Similarity NPC59502
0.7591 Intermediate Similarity NPC303217
0.7581 Intermediate Similarity NPC53953
0.7571 Intermediate Similarity NPC477537
0.7569 Intermediate Similarity NPC7388
0.7569 Intermediate Similarity NPC476942
0.7569 Intermediate Similarity NPC476941
0.7559 Intermediate Similarity NPC291619
0.7559 Intermediate Similarity NPC254958
0.7557 Intermediate Similarity NPC290193
0.7557 Intermediate Similarity NPC4012
0.7557 Intermediate Similarity NPC300098
0.7557 Intermediate Similarity NPC303010
0.7556 Intermediate Similarity NPC324488
0.7556 Intermediate Similarity NPC471995
0.7554 Intermediate Similarity NPC202260
0.7552 Intermediate Similarity NPC475864
0.7552 Intermediate Similarity NPC346
0.7552 Intermediate Similarity NPC276676

  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 NPC79557 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
0.781 Intermediate Similarity NPD2344 Approved
0.7681 Intermediate Similarity NPD2343 Clinical (unspecified phase)
0.7597 Intermediate Similarity NPD1547 Clinical (unspecified phase)
0.7589 Intermediate Similarity NPD2309 Approved
0.7429 Intermediate Similarity NPD1471 Phase 3
0.7302 Intermediate Similarity NPD1241 Discontinued
0.7273 Intermediate Similarity NPD9717 Approved
0.7267 Intermediate Similarity NPD5761 Phase 2
0.7267 Intermediate Similarity NPD5760 Phase 2
0.7226 Intermediate Similarity NPD2313 Discontinued
0.7163 Intermediate Similarity NPD2799 Discontinued
0.7095 Intermediate Similarity NPD920 Approved
0.7075 Intermediate Similarity NPD642 Clinical (unspecified phase)
0.7059 Intermediate Similarity NPD2798 Approved
0.7055 Intermediate Similarity NPD643 Clinical (unspecified phase)
0.7037 Intermediate Similarity NPD1876 Approved
0.7014 Intermediate Similarity NPD1549 Phase 2
0.6993 Remote Similarity NPD2796 Approved
0.6993 Remote Similarity NPD1551 Phase 2
0.6993 Remote Similarity NPD2296 Approved
0.6985 Remote Similarity NPD1203 Approved
0.6974 Remote Similarity NPD6279 Approved
0.6974 Remote Similarity NPD6280 Approved
0.6957 Remote Similarity NPD6832 Phase 2
0.695 Remote Similarity NPD447 Suspended
0.6947 Remote Similarity NPD9092 Discovery
0.6944 Remote Similarity NPD1550 Clinical (unspecified phase)
0.6944 Remote Similarity NPD1552 Clinical (unspecified phase)
0.6944 Remote Similarity NPD2346 Discontinued
0.6934 Remote Similarity NPD1019 Discontinued
0.6918 Remote Similarity NPD1878 Clinical (unspecified phase)
0.6884 Remote Similarity NPD9494 Approved
0.6879 Remote Similarity NPD1240 Approved
0.687 Remote Similarity NPD9493 Approved
0.6857 Remote Similarity NPD411 Approved
0.6849 Remote Similarity NPD1243 Approved
0.6846 Remote Similarity NPD4661 Approved
0.6846 Remote Similarity NPD4662 Approved
0.6812 Remote Similarity NPD5647 Approved
0.6806 Remote Similarity NPD1510 Phase 2
0.6803 Remote Similarity NPD4628 Phase 3
0.6783 Remote Similarity NPD1607 Approved
0.6765 Remote Similarity NPD3972 Approved
0.6753 Remote Similarity NPD6844 Discontinued
0.673 Remote Similarity NPD6808 Phase 2
0.6713 Remote Similarity NPD1899 Clinical (unspecified phase)
0.6707 Remote Similarity NPD6559 Discontinued
0.6689 Remote Similarity NPD6273 Approved
0.6667 Remote Similarity NPD3226 Approved
0.6667 Remote Similarity NPD1247 Approved
0.6667 Remote Similarity NPD2181 Clinical (unspecified phase)
0.6646 Remote Similarity NPD919 Approved
0.6644 Remote Similarity NPD2935 Discontinued
0.6642 Remote Similarity NPD9545 Approved
0.6642 Remote Similarity NPD1608 Approved
0.6624 Remote Similarity NPD3882 Suspended
0.6623 Remote Similarity NPD4378 Clinical (unspecified phase)
0.6623 Remote Similarity NPD5401 Approved
0.6622 Remote Similarity NPD7421 Clinical (unspecified phase)
0.6622 Remote Similarity NPD2800 Approved
0.6617 Remote Similarity NPD405 Clinical (unspecified phase)
0.6607 Remote Similarity NPD8434 Phase 2
0.6603 Remote Similarity NPD7096 Clinical (unspecified phase)
0.6582 Remote Similarity NPD3749 Approved
0.6575 Remote Similarity NPD4308 Phase 3
0.6564 Remote Similarity NPD7893 Clinical (unspecified phase)
0.6562 Remote Similarity NPD290 Approved
0.6556 Remote Similarity NPD6799 Approved
0.6541 Remote Similarity NPD5537 Clinical (unspecified phase)
0.6538 Remote Similarity NPD1934 Approved
0.6536 Remote Similarity NPD5403 Approved
0.6528 Remote Similarity NPD3140 Approved
0.6528 Remote Similarity NPD3142 Approved
0.6522 Remote Similarity NPD5668 Clinical (unspecified phase)
0.6519 Remote Similarity NPD1894 Discontinued
0.6516 Remote Similarity NPD4380 Phase 2
0.6512 Remote Similarity NPD2684 Approved
0.65 Remote Similarity NPD1049 Clinical (unspecified phase)
0.65 Remote Similarity NPD2797 Approved
0.6497 Remote Similarity NPD7819 Suspended
0.6497 Remote Similarity NPD2393 Clinical (unspecified phase)
0.6483 Remote Similarity NPD6355 Discontinued
0.6483 Remote Similarity NPD1933 Approved
0.6481 Remote Similarity NPD3926 Phase 2
0.6478 Remote Similarity NPD7075 Discontinued
0.6478 Remote Similarity NPD4381 Clinical (unspecified phase)
0.6474 Remote Similarity NPD7411 Suspended
0.6463 Remote Similarity NPD7033 Discontinued
0.6463 Remote Similarity NPD3818 Discontinued
0.6457 Remote Similarity NPD1237 Approved
0.6456 Remote Similarity NPD5616 Clinical (unspecified phase)
0.6456 Remote Similarity NPD5402 Approved
0.6456 Remote Similarity NPD8443 Clinical (unspecified phase)
0.6452 Remote Similarity NPD2651 Approved
0.6452 Remote Similarity NPD2649 Approved
0.6443 Remote Similarity NPD2424 Discontinued
0.6442 Remote Similarity NPD4575 Clinical (unspecified phase)
0.6433 Remote Similarity NPD6801 Discontinued
0.6429 Remote Similarity NPD3869 Phase 3
0.6429 Remote Similarity NPD3873 Phase 3
0.6423 Remote Similarity NPD1778 Approved
0.6423 Remote Similarity NPD17 Approved
0.6414 Remote Similarity NPD4307 Phase 2
0.641 Remote Similarity NPD6599 Discontinued
0.6405 Remote Similarity NPD7410 Clinical (unspecified phase)
0.6398 Remote Similarity NPD5494 Approved
0.6389 Remote Similarity NPD6798 Discontinued
0.6389 Remote Similarity NPD3764 Approved
0.6389 Remote Similarity NPD3268 Approved
0.6383 Remote Similarity NPD1470 Approved
0.6376 Remote Similarity NPD6004 Phase 3
0.6376 Remote Similarity NPD6006 Clinical (unspecified phase)
0.6376 Remote Similarity NPD6002 Phase 3
0.6376 Remote Similarity NPD6003 Clinical (unspecified phase)
0.6376 Remote Similarity NPD6005 Phase 3
0.6364 Remote Similarity NPD1609 Clinical (unspecified phase)
0.6358 Remote Similarity NPD3750 Approved
0.6346 Remote Similarity NPD5808 Clinical (unspecified phase)
0.634 Remote Similarity NPD1511 Approved
0.6333 Remote Similarity NPD970 Clinical (unspecified phase)
0.6316 Remote Similarity NPD3887 Approved
0.6316 Remote Similarity NPD7843 Approved
0.6316 Remote Similarity NPD2354 Approved
0.6312 Remote Similarity NPD7768 Phase 2
0.6312 Remote Similarity NPD1283 Approved
0.631 Remote Similarity NPD6764 Approved
0.631 Remote Similarity NPD6765 Approved
0.6309 Remote Similarity NPD5712 Approved
0.6308 Remote Similarity NPD9264 Approved
0.6308 Remote Similarity NPD9267 Approved
0.6308 Remote Similarity NPD9263 Approved
0.6299 Remote Similarity NPD2534 Approved
0.6299 Remote Similarity NPD2532 Approved
0.6299 Remote Similarity NPD2533 Approved
0.6296 Remote Similarity NPD7157 Approved
0.6294 Remote Similarity NPD454 Approved
0.6289 Remote Similarity NPD2801 Approved
0.6286 Remote Similarity NPD1481 Phase 2
0.6268 Remote Similarity NPD6362 Approved
0.6268 Remote Similarity NPD3267 Approved
0.6268 Remote Similarity NPD3266 Approved
0.626 Remote Similarity NPD9266 Approved
0.626 Remote Similarity NPD2182 Approved
0.626 Remote Similarity NPD74 Approved
0.6259 Remote Similarity NPD3496 Discontinued
0.6258 Remote Similarity NPD1512 Approved
0.6242 Remote Similarity NPD3748 Approved
0.6242 Remote Similarity NPD6168 Clinical (unspecified phase)
0.6242 Remote Similarity NPD6166 Phase 2
0.6242 Remote Similarity NPD6167 Clinical (unspecified phase)
0.6233 Remote Similarity NPD4062 Phase 3
0.6233 Remote Similarity NPD6233 Phase 2
0.6232 Remote Similarity NPD1651 Approved
0.6231 Remote Similarity NPD3134 Approved
0.6231 Remote Similarity NPD968 Approved
0.6222 Remote Similarity NPD690 Clinical (unspecified phase)
0.6216 Remote Similarity NPD6653 Approved
0.6214 Remote Similarity NPD1535 Discovery
0.6214 Remote Similarity NPD1201 Approved
0.6202 Remote Similarity NPD164 Approved
0.62 Remote Similarity NPD4477 Approved
0.62 Remote Similarity NPD4476 Approved
0.6194 Remote Similarity NPD821 Approved
0.6188 Remote Similarity NPD1006 Clinical (unspecified phase)
0.6187 Remote Similarity NPD3412 Clinical (unspecified phase)
0.6183 Remote Similarity NPD1358 Approved
0.6169 Remote Similarity NPD7440 Discontinued
0.6168 Remote Similarity NPD2163 Approved
0.6164 Remote Similarity NPD6859 Clinical (unspecified phase)
0.6164 Remote Similarity NPD1699 Clinical (unspecified phase)
0.6163 Remote Similarity NPD6784 Approved
0.6163 Remote Similarity NPD6785 Approved
0.6159 Remote Similarity NPD2355 Clinical (unspecified phase)
0.6159 Remote Similarity NPD2353 Approved
0.6154 Remote Similarity NPD5953 Discontinued
0.6154 Remote Similarity NPD9697 Approved
0.6149 Remote Similarity NPD3817 Phase 2
0.6145 Remote Similarity NPD7852 Clinical (unspecified phase)
0.6144 Remote Similarity NPD7003 Approved
0.6144 Remote Similarity NPD4110 Phase 3
0.6144 Remote Similarity NPD4109 Clinical (unspecified phase)
0.6142 Remote Similarity NPD1238 Approved
0.6131 Remote Similarity NPD7804 Clinical (unspecified phase)
0.6127 Remote Similarity NPD4379 Clinical (unspecified phase)
0.6125 Remote Similarity NPD7577 Discontinued
0.6124 Remote Similarity NPD9261 Approved
0.6118 Remote Similarity NPD4534 Discontinued
0.6118 Remote Similarity NPD5958 Discontinued
0.6115 Remote Similarity NPD5585 Approved
0.6104 Remote Similarity NPD3295 Clinical (unspecified phase)
0.6099 Remote Similarity NPD1281 Approved
0.6095 Remote Similarity NPD1729 Discontinued
0.6095 Remote Similarity NPD7074 Phase 3
0.6093 Remote Similarity NPD1501 Clinical (unspecified phase)
0.6093 Remote Similarity NPD6032 Approved
0.609 Remote Similarity NPD7004 Clinical (unspecified phase)
0.6087 Remote Similarity NPD5536 Phase 2
0.6082 Remote Similarity NPD4419 Clinical (unspecified phase)
0.6081 Remote Similarity NPD4140 Approved
0.608 Remote Similarity NPD3269 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