Structure

Physi-Chem Properties

Molecular Weight:  366.22
Volume:  411.826
LogP:  6.362
LogD:  4.802
LogS:  -4.712
# Rotatable Bonds:  8
TPSA:  50.44
# H-Bond Aceptor:  3
# H-Bond Donor:  1
# Rings:  2
# Heavy Atoms:  3

MedChem Properties

QED Drug-Likeness Score:  0.431
Synthetic Accessibility Score:  2.812
Fsp3:  0.375
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Rejected
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:  -4.794
MDCK Permeability:  2.6489762603887357e-05
Pgp-inhibitor:  0.991
Pgp-substrate:  0.066
Human Intestinal Absorption (HIA):  0.04
20% Bioavailability (F20%):  0.078
30% Bioavailability (F30%):  0.005

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.028
Plasma Protein Binding (PPB):  98.49502563476562%
Volume Distribution (VD):  0.536
Pgp-substrate:  1.3200900554656982%

ADMET: Metabolism

CYP1A2-inhibitor:  0.932
CYP1A2-substrate:  0.226
CYP2C19-inhibitor:  0.844
CYP2C19-substrate:  0.121
CYP2C9-inhibitor:  0.919
CYP2C9-substrate:  0.973
CYP2D6-inhibitor:  0.378
CYP2D6-substrate:  0.804
CYP3A4-inhibitor:  0.447
CYP3A4-substrate:  0.117

ADMET: Excretion

Clearance (CL):  2.788
Half-life (T1/2):  0.131

ADMET: Toxicity

hERG Blockers:  0.007
Human Hepatotoxicity (H-HT):  0.921
Drug-inuced Liver Injury (DILI):  0.06
AMES Toxicity:  0.003
Rat Oral Acute Toxicity:  0.008
Maximum Recommended Daily Dose:  0.18
Skin Sensitization:  0.953
Carcinogencity:  0.049
Eye Corrosion:  0.003
Eye Irritation:  0.124
Respiratory Toxicity:  0.05

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

  Natural Product: NPC470092

Natural Product ID:  NPC470092
Common Name*:   Ferulenol
IUPAC Name:   n.a.
Synonyms:   Ferulenol
Standard InCHIKey:  PRSOPHSUKXJKIM-CFBAGHHKSA-N
Standard InCHI:  InChI=1S/C24H30O3/c1-17(2)9-7-10-18(3)11-8-12-19(4)15-16-21-23(25)20-13-5-6-14-22(20)27-24(21)26/h5-6,9,11,13-15,26H,7-8,10,12,16H2,1-4H3/b18-11+,19-15+
SMILES:  C/C(=CCc1c(O)oc2c(c1=O)cccc2)/CC/C=C(/CCC=C(C)C)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL174839
PubChem CID:   n.a.
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0000259] Prenol lipids
        • [CHEMONTID:0001550] Sesquiterpenoids

*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
NPO25999 Ferula communis Species Apiaceae Eukaryota n.a. n.a. n.a. PMID[15620264]
NPO25999 Ferula communis 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
NPT5372 Individual Protein Squalene-hopene cyclase Alicyclobacillus acidocaldarius subsp. acidocaldarius (strain ATCC27009 / DSM 446 / 104-1A) (Bacillus acidocaldarius) IC50 = 90000.0 nM PMID[487927]
NPT368 Cell Line SN12C Homo sapiens GI50 n.a. 100000.0 nM PMID[487930]
NPT370 Cell Line NCI-H23 Homo sapiens GI50 n.a. 55847.02 nM PMID[487930]
NPT371 Cell Line UO-31 Homo sapiens GI50 n.a. 48752.85 nM PMID[487930]
NPT369 Cell Line ACHN Homo sapiens GI50 n.a. 100000.0 nM PMID[487930]
NPT372 Cell Line HOP-92 Homo sapiens GI50 n.a. 100000.0 nM PMID[487930]
NPT116 Cell Line HL-60 Homo sapiens GI50 n.a. 99083.19 nM PMID[487930]
NPT374 Cell Line SF-539 Homo sapiens GI50 n.a. 100000.0 nM PMID[487930]
NPT375 Cell Line Malme-3M Homo sapiens GI50 n.a. 100000.0 nM PMID[487930]
NPT111 Cell Line K562 Homo sapiens GI50 n.a. 80537.84 nM PMID[487930]
NPT377 Cell Line OVCAR-3 Homo sapiens GI50 n.a. 75509.22 nM PMID[487930]
NPT112 Cell Line MOLT-4 Homo sapiens GI50 n.a. 100000.0 nM PMID[487930]
NPT379 Cell Line HOP-62 Homo sapiens GI50 n.a. 100000.0 nM PMID[487930]
NPT380 Cell Line U-251 Homo sapiens GI50 n.a. 57942.87 nM PMID[487930]
NPT381 Cell Line OVCAR-8 Homo sapiens GI50 n.a. 100000.0 nM PMID[487930]
NPT572 Cell Line DMS-273 Homo sapiens GI50 n.a. 100000.0 nM PMID[487930]
NPT383 Cell Line SNB-19 Homo sapiens GI50 n.a. 100000.0 nM PMID[487930]
NPT384 Cell Line TK-10 Homo sapiens GI50 n.a. 100000.0 nM PMID[487930]
NPT385 Cell Line SR Homo sapiens GI50 n.a. 100000.0 nM PMID[487930]
NPT323 Cell Line SW-620 Homo sapiens GI50 n.a. 100000.0 nM PMID[487930]
NPT573 Cell Line M19-MEL Homo sapiens GI50 n.a. 100000.0 nM PMID[487930]
NPT455 Cell Line NCI-H522 Homo sapiens GI50 n.a. 100000.0 nM PMID[487930]
NPT386 Cell Line KM12 Homo sapiens GI50 n.a. 100000.0 nM PMID[487930]
NPT574 Cell Line XF498 Homo sapiens GI50 n.a. 100000.0 nM PMID[487930]
NPT387 Cell Line M14 Homo sapiens GI50 n.a. 100000.0 nM PMID[487930]
NPT388 Cell Line NCI-H322M Homo sapiens GI50 n.a. 100000.0 nM PMID[487930]
NPT389 Cell Line RPMI-8226 Homo sapiens GI50 n.a. 91622.05 nM PMID[487930]
NPT456 Cell Line OVCAR-4 Homo sapiens GI50 n.a. 100000.0 nM PMID[487930]
NPT390 Cell Line LOX IMVI Homo sapiens GI50 n.a. 100000.0 nM PMID[487930]
NPT147 Cell Line SK-MEL-2 Homo sapiens GI50 n.a. 100000.0 nM PMID[487930]
NPT81 Cell Line A549 Homo sapiens GI50 n.a. 65614.53 nM PMID[487930]
NPT575 Cell Line KM-20L2 Homo sapiens GI50 n.a. 100000.0 nM PMID[487930]
NPT391 Cell Line HCC 2998 Homo sapiens GI50 n.a. 100000.0 nM PMID[487930]
NPT392 Cell Line SNB-75 Homo sapiens GI50 n.a. 100000.0 nM PMID[487930]
NPT148 Cell Line HCT-15 Homo sapiens GI50 n.a. 69023.98 nM PMID[487930]
NPT393 Cell Line HCT-116 Homo sapiens GI50 n.a. 89125.09 nM PMID[487930]
NPT395 Cell Line SF-268 Homo sapiens GI50 n.a. 100000.0 nM PMID[487930]
NPT394 Cell Line EKVX Homo sapiens GI50 n.a. 100000.0 nM PMID[487930]
NPT731 Cell Line LXFL 529 Homo sapiens GI50 n.a. 100000.0 nM PMID[487930]
NPT576 Cell Line DMS-114 Homo sapiens GI50 n.a. 83560.3 nM PMID[487930]
NPT146 Cell Line SK-OV-3 Homo sapiens GI50 n.a. 100000.0 nM PMID[487930]
NPT397 Cell Line NCI-H460 Homo sapiens GI50 n.a. 100000.0 nM PMID[487930]
NPT398 Cell Line UACC-62 Homo sapiens GI50 n.a. 63679.55 nM PMID[487930]
NPT458 Cell Line IGROV-1 Homo sapiens GI50 n.a. 100000.0 nM PMID[487930]
NPT399 Cell Line SF-295 Homo sapiens GI50 n.a. 100000.0 nM PMID[487930]
NPT578 Cell Line SNB-78 Homo sapiens GI50 n.a. 100000.0 nM PMID[487930]
NPT403 Cell Line UACC-257 Homo sapiens GI50 n.a. 99770.01 nM PMID[487930]
NPT401 Cell Line 786-0 Homo sapiens GI50 n.a. 100000.0 nM PMID[487930]
NPT579 Cell Line DLD-1 Homo sapiens GI50 n.a. 100000.0 nM PMID[487930]
NPT404 Cell Line CCRF-CEM Homo sapiens GI50 n.a. 100000.0 nM PMID[487930]
NPT405 Cell Line NCI-H226 Homo sapiens GI50 n.a. 47097.73 nM PMID[487930]
NPT170 Cell Line SK-MEL-28 Homo sapiens GI50 n.a. 100000.0 nM PMID[487930]
NPT139 Cell Line HT-29 Homo sapiens GI50 n.a. 100000.0 nM PMID[487930]
NPT406 Cell Line RXF 393 Homo sapiens GI50 n.a. 99083.19 nM PMID[487930]
NPT407 Cell Line COLO 205 Homo sapiens GI50 n.a. 100000.0 nM PMID[487930]
NPT732 Cell Line HOP-18 Homo sapiens GI50 n.a. 100000.0 nM PMID[487930]
NPT2 Others Unspecified IC50 = 98.0 nM PMID[487928]
NPT1176 Organism Mycobacterium fortuitum Mycobacterium fortuitum MIC = 2.0 ug.mL-1 PMID[487929]
NPT1177 Organism Mycobacterium phlei Mycobacterium phlei MIC = 2.0 ug.mL-1 PMID[487929]
NPT5246 Organism Mycobacterium aurum Mycobacterium aurum MIC = 2.0 ug.mL-1 PMID[487929]
NPT602 Organism Mycobacterium smegmatis Mycobacterium smegmatis MIC = 0.5 ug.mL-1 PMID[487929]
NPT348 Organism Myzus persicae Myzus persicae Inhibition = 62.0 % PMID[487931]
NPT348 Organism Myzus persicae Myzus persicae Inhibition = 71.0 % PMID[487931]
NPT348 Organism Myzus persicae Myzus persicae Inhibition = 63.0 % PMID[487931]
NPT348 Organism Myzus persicae Myzus persicae Inhibition = 26.0 % PMID[487931]
NPT348 Organism Myzus persicae Myzus persicae Inhibition = 20.0 % PMID[487931]
NPT348 Organism Myzus persicae Myzus persicae Inhibition = 28.0 % PMID[487931]
NPT6293 Organism Mycobacterium sp. Mycobacterium sp. MIC = 2.0 ug.mL-1 PMID[487932]

☑ 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 NPC470092 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
0.9035 High Similarity NPC279916
0.8898 High Similarity NPC54243
0.8814 High Similarity NPC32298
0.8739 High Similarity NPC201284
0.8718 High Similarity NPC188907
0.8707 High Similarity NPC53953
0.8689 High Similarity NPC93730
0.8655 High Similarity NPC171023
0.8618 High Similarity NPC193805
0.8618 High Similarity NPC56332
0.8583 High Similarity NPC35744
0.8571 High Similarity NPC187907
0.8571 High Similarity NPC217423
0.8548 High Similarity NPC2771
0.8537 High Similarity NPC472888
0.848 Intermediate Similarity NPC474264
0.8475 Intermediate Similarity NPC114144
0.8455 Intermediate Similarity NPC311219
0.845 Intermediate Similarity NPC477536
0.8438 Intermediate Similarity NPC324488
0.8435 Intermediate Similarity NPC224584
0.8425 Intermediate Similarity NPC473019
0.8417 Intermediate Similarity NPC469954
0.8413 Intermediate Similarity NPC22783
0.8413 Intermediate Similarity NPC298884
0.84 Intermediate Similarity NPC4164
0.8387 Intermediate Similarity NPC182646
0.8376 Intermediate Similarity NPC23332
0.8374 Intermediate Similarity NPC314329
0.8361 Intermediate Similarity NPC230951
0.8361 Intermediate Similarity NPC474874
0.8359 Intermediate Similarity NPC7569
0.8346 Intermediate Similarity NPC125887
0.8333 Intermediate Similarity NPC477534
0.8333 Intermediate Similarity NPC128825
0.8333 Intermediate Similarity NPC19290
0.8321 Intermediate Similarity NPC298900
0.832 Intermediate Similarity NPC470162
0.832 Intermediate Similarity NPC470163
0.8291 Intermediate Similarity NPC183648
0.8281 Intermediate Similarity NPC211120
0.8279 Intermediate Similarity NPC328459
0.8279 Intermediate Similarity NPC90522
0.8268 Intermediate Similarity NPC470841
0.8268 Intermediate Similarity NPC41721
0.8268 Intermediate Similarity NPC293387
0.8264 Intermediate Similarity NPC45104
0.8254 Intermediate Similarity NPC65041
0.8254 Intermediate Similarity NPC224657
0.8244 Intermediate Similarity NPC188646
0.8244 Intermediate Similarity NPC263670
0.8244 Intermediate Similarity NPC312318
0.8244 Intermediate Similarity NPC472365
0.8244 Intermediate Similarity NPC242294
0.8244 Intermediate Similarity NPC192304
0.8244 Intermediate Similarity NPC56031
0.8244 Intermediate Similarity NPC139813
0.8244 Intermediate Similarity NPC337373
0.8244 Intermediate Similarity NPC175098
0.824 Intermediate Similarity NPC473942
0.8231 Intermediate Similarity NPC186097
0.8231 Intermediate Similarity NPC475009
0.8231 Intermediate Similarity NPC64359
0.8231 Intermediate Similarity NPC475008
0.8231 Intermediate Similarity NPC118253
0.8231 Intermediate Similarity NPC308037
0.8231 Intermediate Similarity NPC474340
0.8231 Intermediate Similarity NPC262359
0.8217 Intermediate Similarity NPC39753
0.8217 Intermediate Similarity NPC115998
0.8211 Intermediate Similarity NPC72977
0.8203 Intermediate Similarity NPC80694
0.8203 Intermediate Similarity NPC186098
0.8203 Intermediate Similarity NPC475017
0.8197 Intermediate Similarity NPC94637
0.8189 Intermediate Similarity NPC237868
0.8182 Intermediate Similarity NPC281513
0.8182 Intermediate Similarity NPC286336
0.8182 Intermediate Similarity NPC22222
0.8175 Intermediate Similarity NPC313039
0.8175 Intermediate Similarity NPC473976
0.8175 Intermediate Similarity NPC109812
0.8175 Intermediate Similarity NPC131043
0.8175 Intermediate Similarity NPC6888
0.8175 Intermediate Similarity NPC91475
0.8175 Intermediate Similarity NPC4012
0.8175 Intermediate Similarity NPC198459
0.8175 Intermediate Similarity NPC265910
0.8168 Intermediate Similarity NPC212631
0.8168 Intermediate Similarity NPC205468
0.8168 Intermediate Similarity NPC10971
0.8168 Intermediate Similarity NPC257756
0.8168 Intermediate Similarity NPC87231
0.8168 Intermediate Similarity NPC129132
0.8154 Intermediate Similarity NPC301717
0.8154 Intermediate Similarity NPC137264
0.8154 Intermediate Similarity NPC205360
0.8148 Intermediate Similarity NPC477537
0.814 Intermediate Similarity NPC197425
0.814 Intermediate Similarity NPC60558
0.814 Intermediate Similarity NPC238309
0.8125 Intermediate Similarity NPC71525
0.8125 Intermediate Similarity NPC264428
0.8125 Intermediate Similarity NPC45537
0.812 Intermediate Similarity NPC131039
0.8115 Intermediate Similarity NPC240664
0.8115 Intermediate Similarity NPC269414
0.8106 Intermediate Similarity NPC82225
0.8106 Intermediate Similarity NPC18877
0.8106 Intermediate Similarity NPC294593
0.8106 Intermediate Similarity NPC204960
0.8106 Intermediate Similarity NPC223354
0.8106 Intermediate Similarity NPC159623
0.8106 Intermediate Similarity NPC20560
0.8106 Intermediate Similarity NPC144051
0.8106 Intermediate Similarity NPC28753
0.8092 Intermediate Similarity NPC313618
0.8092 Intermediate Similarity NPC470160
0.8092 Intermediate Similarity NPC284424
0.8087 Intermediate Similarity NPC38209
0.8077 Intermediate Similarity NPC278787
0.8077 Intermediate Similarity NPC327457
0.8077 Intermediate Similarity NPC86774
0.8077 Intermediate Similarity NPC185497
0.8074 Intermediate Similarity NPC473988
0.8065 Intermediate Similarity NPC233282
0.8062 Intermediate Similarity NPC196034
0.8062 Intermediate Similarity NPC473907
0.806 Intermediate Similarity NPC41461
0.806 Intermediate Similarity NPC472367
0.806 Intermediate Similarity NPC274109
0.806 Intermediate Similarity NPC66349
0.806 Intermediate Similarity NPC476333
0.806 Intermediate Similarity NPC150399
0.806 Intermediate Similarity NPC473391
0.806 Intermediate Similarity NPC25287
0.806 Intermediate Similarity NPC168105
0.806 Intermediate Similarity NPC472364
0.806 Intermediate Similarity NPC240593
0.806 Intermediate Similarity NPC186838
0.806 Intermediate Similarity NPC13408
0.806 Intermediate Similarity NPC1486
0.806 Intermediate Similarity NPC477244
0.806 Intermediate Similarity NPC249606
0.806 Intermediate Similarity NPC98115
0.806 Intermediate Similarity NPC213603
0.806 Intermediate Similarity NPC12165
0.806 Intermediate Similarity NPC477243
0.806 Intermediate Similarity NPC477242
0.8051 Intermediate Similarity NPC234639
0.8034 Intermediate Similarity NPC141523
0.8033 Intermediate Similarity NPC33717
0.8033 Intermediate Similarity NPC477453
0.8033 Intermediate Similarity NPC470860
0.8031 Intermediate Similarity NPC89630
0.803 Intermediate Similarity NPC101294
0.803 Intermediate Similarity NPC473655
0.803 Intermediate Similarity NPC287533
0.803 Intermediate Similarity NPC229646
0.803 Intermediate Similarity NPC182428
0.8017 Intermediate Similarity NPC227255
0.8016 Intermediate Similarity NPC46634
0.8015 Intermediate Similarity NPC477535
0.8015 Intermediate Similarity NPC141549
0.8015 Intermediate Similarity NPC5515
0.8015 Intermediate Similarity NPC270369
0.8 Intermediate Similarity NPC253616
0.8 Intermediate Similarity NPC153979
0.8 Intermediate Similarity NPC188879
0.8 Intermediate Similarity NPC57552
0.8 Intermediate Similarity NPC303644
0.8 Intermediate Similarity NPC7013
0.8 Intermediate Similarity NPC298224
0.8 Intermediate Similarity NPC250266
0.8 Intermediate Similarity NPC228661
0.8 Intermediate Similarity NPC266597
0.8 Intermediate Similarity NPC209560
0.8 Intermediate Similarity NPC472419
0.8 Intermediate Similarity NPC181124
0.8 Intermediate Similarity NPC116632
0.8 Intermediate Similarity NPC473894
0.8 Intermediate Similarity NPC294409
0.8 Intermediate Similarity NPC162680
0.8 Intermediate Similarity NPC317119
0.8 Intermediate Similarity NPC332594
0.7985 Intermediate Similarity NPC151113
0.7985 Intermediate Similarity NPC156092
0.7985 Intermediate Similarity NPC13575
0.7985 Intermediate Similarity NPC472881
0.7984 Intermediate Similarity NPC121104
0.7984 Intermediate Similarity NPC305518
0.7984 Intermediate Similarity NPC264976
0.7984 Intermediate Similarity NPC43435
0.7984 Intermediate Similarity NPC37512
0.7984 Intermediate Similarity NPC475496
0.7984 Intermediate Similarity NPC61779
0.7984 Intermediate Similarity NPC49852
0.7984 Intermediate Similarity NPC128428
0.7984 Intermediate Similarity NPC181715
0.797 Intermediate Similarity NPC57601

  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 NPC470092 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
0.9412 High Similarity NPD2798 Approved
0.8455 Intermediate Similarity NPD9717 Approved
0.8374 Intermediate Similarity NPD1547 Clinical (unspecified phase)
0.8359 Intermediate Similarity NPD2313 Discontinued
0.8346 Intermediate Similarity NPD6832 Phase 2
0.8333 Intermediate Similarity NPD9493 Approved
0.8258 Intermediate Similarity NPD2799 Discontinued
0.8254 Intermediate Similarity NPD1203 Approved
0.8222 Intermediate Similarity NPD1878 Clinical (unspecified phase)
0.8092 Intermediate Similarity NPD1240 Approved
0.8083 Intermediate Similarity NPD1241 Discontinued
0.806 Intermediate Similarity NPD2935 Discontinued
0.803 Intermediate Similarity NPD1933 Approved
0.8016 Intermediate Similarity NPD3972 Approved
0.797 Intermediate Similarity NPD1607 Approved
0.7969 Intermediate Similarity NPD2797 Approved
0.7926 Intermediate Similarity NPD2796 Approved
0.7907 Intermediate Similarity NPD1019 Discontinued
0.7881 Intermediate Similarity NPD9264 Approved
0.7881 Intermediate Similarity NPD9263 Approved
0.7881 Intermediate Similarity NPD9267 Approved
0.7868 Intermediate Similarity NPD2346 Discontinued
0.7868 Intermediate Similarity NPD2344 Approved
0.7852 Intermediate Similarity NPD1510 Phase 2
0.7845 Intermediate Similarity NPD9261 Approved
0.7815 Intermediate Similarity NPD74 Approved
0.7815 Intermediate Similarity NPD9266 Approved
0.7803 Intermediate Similarity NPD411 Approved
0.7803 Intermediate Similarity NPD3268 Approved
0.7786 Intermediate Similarity NPD6799 Approved
0.7761 Intermediate Similarity NPD447 Suspended
0.7761 Intermediate Similarity NPD1899 Clinical (unspecified phase)
0.7752 Intermediate Similarity NPD1876 Approved
0.7742 Intermediate Similarity NPD405 Clinical (unspecified phase)
0.7721 Intermediate Similarity NPD4308 Phase 3
0.7712 Intermediate Similarity NPD9697 Approved
0.7692 Intermediate Similarity NPD3267 Approved
0.7692 Intermediate Similarity NPD3266 Approved
0.7687 Intermediate Similarity NPD4307 Phase 2
0.7643 Intermediate Similarity NPD2309 Approved
0.7626 Intermediate Similarity NPD7421 Clinical (unspecified phase)
0.7622 Intermediate Similarity NPD5403 Approved
0.7606 Intermediate Similarity NPD4378 Clinical (unspecified phase)
0.7606 Intermediate Similarity NPD5401 Approved
0.7606 Intermediate Similarity NPD7410 Clinical (unspecified phase)
0.7606 Intermediate Similarity NPD4662 Approved
0.7606 Intermediate Similarity NPD4661 Approved
0.7554 Intermediate Similarity NPD1549 Phase 2
0.7554 Intermediate Similarity NPD970 Clinical (unspecified phase)
0.7536 Intermediate Similarity NPD1551 Phase 2
0.75 Intermediate Similarity NPD3134 Approved
0.75 Intermediate Similarity NPD1243 Approved
0.7482 Intermediate Similarity NPD2343 Clinical (unspecified phase)
0.7482 Intermediate Similarity NPD1550 Clinical (unspecified phase)
0.7482 Intermediate Similarity NPD1552 Clinical (unspecified phase)
0.748 Intermediate Similarity NPD9545 Approved
0.7466 Intermediate Similarity NPD6599 Discontinued
0.7464 Intermediate Similarity NPD3748 Approved
0.7447 Intermediate Similarity NPD3750 Approved
0.7447 Intermediate Similarity NPD7003 Approved
0.744 Intermediate Similarity NPD9281 Approved
0.7426 Intermediate Similarity NPD3140 Approved
0.7426 Intermediate Similarity NPD3142 Approved
0.7415 Intermediate Similarity NPD7411 Suspended
0.74 Intermediate Similarity NPD4381 Clinical (unspecified phase)
0.7397 Intermediate Similarity NPD7458 Discontinued
0.7397 Intermediate Similarity NPD3226 Approved
0.7394 Intermediate Similarity NPD3295 Clinical (unspecified phase)
0.7385 Intermediate Similarity NPD1201 Approved
0.7383 Intermediate Similarity NPD7318 Phase 3
0.7365 Intermediate Similarity NPD6844 Discontinued
0.7365 Intermediate Similarity NPD6801 Discontinued
0.7364 Intermediate Similarity NPD4626 Approved
0.7351 Intermediate Similarity NPD3252 Approved
0.7348 Intermediate Similarity NPD3225 Approved
0.7347 Intermediate Similarity NPD4380 Phase 2
0.7344 Intermediate Similarity NPD1894 Discontinued
0.7339 Intermediate Similarity NPD1609 Clinical (unspecified phase)
0.7328 Intermediate Similarity NPD1608 Approved
0.7315 Intermediate Similarity NPD7096 Clinical (unspecified phase)
0.7315 Intermediate Similarity NPD7819 Suspended
0.7308 Intermediate Similarity NPD3496 Discontinued
0.7308 Intermediate Similarity NPD3847 Discontinued
0.7295 Intermediate Similarity NPD1358 Approved
0.7293 Intermediate Similarity NPD1470 Approved
0.7293 Intermediate Similarity NPD1164 Approved
0.7292 Intermediate Similarity NPD1511 Approved
0.7287 Intermediate Similarity NPD1651 Approved
0.7287 Intermediate Similarity NPD4196 Clinical (unspecified phase)
0.7279 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.7279 Intermediate Similarity NPD6798 Discontinued
0.7267 Intermediate Similarity NPD3817 Phase 2
0.7267 Intermediate Similarity NPD5402 Approved
0.7266 Intermediate Similarity NPD5536 Phase 2
0.7254 Intermediate Similarity NPD2654 Approved
0.7252 Intermediate Similarity NPD422 Phase 1
0.7248 Intermediate Similarity NPD7317 Phase 3
0.7244 Intermediate Similarity NPD709 Approved
0.7234 Intermediate Similarity NPD1471 Phase 3
0.7231 Intermediate Similarity NPD1778 Approved
0.7231 Intermediate Similarity NPD17 Approved
0.723 Intermediate Similarity NPD6585 Discontinued
0.7222 Intermediate Similarity NPD643 Clinical (unspecified phase)
0.7218 Intermediate Similarity NPD1283 Approved
0.7214 Intermediate Similarity NPD7033 Discontinued
0.7203 Intermediate Similarity NPD4628 Phase 3
0.72 Intermediate Similarity NPD2801 Approved
0.7197 Intermediate Similarity NPD1481 Phase 2
0.7194 Intermediate Similarity NPD6651 Approved
0.7192 Intermediate Similarity NPD1512 Approved
0.7192 Intermediate Similarity NPD5049 Phase 3
0.7185 Intermediate Similarity NPD9494 Approved
0.7181 Intermediate Similarity NPD5890 Approved
0.7181 Intermediate Similarity NPD5889 Approved
0.7171 Intermediate Similarity NPD7075 Discontinued
0.7154 Intermediate Similarity NPD5691 Approved
0.7154 Intermediate Similarity NPD9265 Clinical (unspecified phase)
0.7153 Intermediate Similarity NPD2354 Approved
0.7143 Intermediate Similarity NPD920 Approved
0.7143 Intermediate Similarity NPD4379 Clinical (unspecified phase)
0.7143 Intermediate Similarity NPD5535 Approved
0.7143 Intermediate Similarity NPD1238 Approved
0.7143 Intermediate Similarity NPD1138 Approved
0.7123 Intermediate Similarity NPD642 Clinical (unspecified phase)
0.7122 Intermediate Similarity NPD6355 Discontinued
0.7121 Intermediate Similarity NPD1535 Discovery
0.7121 Intermediate Similarity NPD1281 Approved
0.712 Intermediate Similarity NPD2181 Clinical (unspecified phase)
0.7113 Intermediate Similarity NPD2353 Approved
0.7113 Intermediate Similarity NPD2355 Clinical (unspecified phase)
0.7111 Intermediate Similarity NPD5647 Approved
0.7109 Intermediate Similarity NPD6671 Approved
0.7109 Intermediate Similarity NPD6387 Discontinued
0.7105 Intermediate Similarity NPD7768 Phase 2
0.7105 Intermediate Similarity NPD3882 Suspended
0.7097 Intermediate Similarity NPD2684 Approved
0.7097 Intermediate Similarity NPD2182 Approved
0.7086 Intermediate Similarity NPD2393 Clinical (unspecified phase)
0.7067 Intermediate Similarity NPD2366 Approved
0.7063 Intermediate Similarity NPD1137 Approved
0.7063 Intermediate Similarity NPD1139 Approved
0.7049 Intermediate Similarity NPD164 Approved
0.7049 Intermediate Similarity NPD5909 Discontinued
0.7047 Intermediate Similarity NPD2649 Approved
0.7047 Intermediate Similarity NPD2651 Approved
0.7042 Intermediate Similarity NPD4477 Approved
0.7042 Intermediate Similarity NPD4476 Approved
0.7039 Intermediate Similarity NPD2296 Approved
0.7039 Intermediate Similarity NPD8443 Clinical (unspecified phase)
0.7034 Intermediate Similarity NPD3887 Approved
0.7031 Intermediate Similarity NPD690 Clinical (unspecified phase)
0.7029 Intermediate Similarity NPD1296 Phase 2
0.7029 Intermediate Similarity NPD3764 Approved
0.7027 Intermediate Similarity NPD6980 Clinical (unspecified phase)
0.7025 Intermediate Similarity NPD3818 Discontinued
0.7023 Intermediate Similarity NPD5585 Approved
0.702 Intermediate Similarity NPD1934 Approved
0.702 Intermediate Similarity NPD6279 Approved
0.702 Intermediate Similarity NPD6280 Approved
0.7016 Intermediate Similarity NPD290 Approved
0.7014 Intermediate Similarity NPD2800 Approved
0.7007 Intermediate Similarity NPD2614 Approved
0.7 Intermediate Similarity NPD4618 Approved
0.7 Intermediate Similarity NPD4622 Approved
0.6986 Remote Similarity NPD7440 Discontinued
0.6981 Remote Similarity NPD7804 Clinical (unspecified phase)
0.6981 Remote Similarity NPD7054 Approved
0.6978 Remote Similarity NPD6233 Phase 2
0.6978 Remote Similarity NPD4062 Phase 3
0.6978 Remote Similarity NPD520 Approved
0.6966 Remote Similarity NPD6398 Clinical (unspecified phase)
0.696 Remote Similarity NPD6831 Clinical (unspecified phase)
0.6959 Remote Similarity NPD6273 Approved
0.6948 Remote Similarity NPD3749 Approved
0.6939 Remote Similarity NPD6143 Clinical (unspecified phase)
0.6937 Remote Similarity NPD7472 Approved
0.6933 Remote Similarity NPD5808 Clinical (unspecified phase)
0.6929 Remote Similarity NPD943 Approved
0.6929 Remote Similarity NPD2203 Discontinued
0.6911 Remote Similarity NPD1237 Approved
0.6905 Remote Similarity NPD5451 Approved
0.6901 Remote Similarity NPD5688 Approved
0.6901 Remote Similarity NPD5689 Approved
0.6899 Remote Similarity NPD7852 Clinical (unspecified phase)
0.6897 Remote Similarity NPD9258 Approved
0.6897 Remote Similarity NPD9256 Approved
0.6894 Remote Similarity NPD6797 Phase 2
0.6892 Remote Similarity NPD2532 Approved
0.6892 Remote Similarity NPD2534 Approved
0.6892 Remote Similarity NPD2533 Approved
0.6879 Remote Similarity NPD1184 Approved
0.6875 Remote Similarity NPD7843 Approved
0.6871 Remote Similarity NPD160 Clinical (unspecified phase)
0.6864 Remote Similarity NPD1202 Approved
0.686 Remote Similarity NPD2066 Phase 3
0.6857 Remote Similarity NPD8032 Phase 2
0.6852 Remote Similarity NPD7251 Discontinued
0.6852 Remote Similarity NPD6559 Discontinued
0.6842 Remote Similarity NPD9259 Approved
0.6842 Remote Similarity NPD9257 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