Structure

Physi-Chem Properties

Molecular Weight:  232.11
Volume:  246.776
LogP:  3.254
LogD:  3.303
LogS:  -3.911
# Rotatable Bonds:  2
TPSA:  35.53
# H-Bond Aceptor:  3
# H-Bond Donor:  0
# Rings:  2
# Heavy Atoms:  3

MedChem Properties

QED Drug-Likeness Score:  0.735
Synthetic Accessibility Score:  2.607
Fsp3:  0.357
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Rejected
GSK Rule:  Accepted
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.63
MDCK Permeability:  2.1777208530693315e-05
Pgp-inhibitor:  0.979
Pgp-substrate:  0.001
Human Intestinal Absorption (HIA):  0.006
20% Bioavailability (F20%):  0.021
30% Bioavailability (F30%):  0.418

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.558
Plasma Protein Binding (PPB):  90.50720977783203%
Volume Distribution (VD):  1.077
Pgp-substrate:  8.521224975585938%

ADMET: Metabolism

CYP1A2-inhibitor:  0.965
CYP1A2-substrate:  0.89
CYP2C19-inhibitor:  0.817
CYP2C19-substrate:  0.789
CYP2C9-inhibitor:  0.507
CYP2C9-substrate:  0.875
CYP2D6-inhibitor:  0.801
CYP2D6-substrate:  0.733
CYP3A4-inhibitor:  0.204
CYP3A4-substrate:  0.566

ADMET: Excretion

Clearance (CL):  6.02
Half-life (T1/2):  0.407

ADMET: Toxicity

hERG Blockers:  0.029
Human Hepatotoxicity (H-HT):  0.859
Drug-inuced Liver Injury (DILI):  0.365
AMES Toxicity:  0.025
Rat Oral Acute Toxicity:  0.075
Maximum Recommended Daily Dose:  0.095
Skin Sensitization:  0.211
Carcinogencity:  0.887
Eye Corrosion:  0.007
Eye Irritation:  0.378
Respiratory Toxicity:  0.892

Download Data

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Structure MOL file  
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Biological Activities  
Similar NPs/Drugs  

  Natural Product: NPC229646

Natural Product ID:  NPC229646
Common Name*:   Encecalin
IUPAC Name:   1-(7-methoxy-2,2-dimethylchromen-6-yl)ethanone
Synonyms:   Encecalin
Standard InCHIKey:  WXVLCNREBFDEKS-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C14H16O3/c1-9(15)11-7-10-5-6-14(2,3)17-12(10)8-13(11)16-4/h5-8H,1-4H3
SMILES:  COc1cc2OC(C)(C)C=Cc2cc1C(=O)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL451983
PubChem CID:   114703
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000002] Organoheterocyclic compounds
      • [CHEMONTID:0000123] Benzopyrans
        • [CHEMONTID:0003410] 1-benzopyrans
          • [CHEMONTID:0003522] 2,2-dimethyl-1-benzopyrans

*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
NPO3610 Strychnos panganensis Species Loganiaceae Eukaryota n.a. n.a. n.a. PMID[12398531]
NPO26371 Sorghum bicolor Species Poaceae Eukaryota n.a. n.a. n.a. PMID[12542343]
NPO26371 Sorghum bicolor Species Poaceae Eukaryota roots n.a. n.a. PMID[14664512]
NPO4211 Negombata corticata Species Latrunculiidae Eukaryota n.a. formosan n.a. PMID[20718475]
NPO17034 Panagrellus redivivus Species Panagrolaimidae Eukaryota n.a. n.a. n.a. PMID[23213209]
NPO26371 Sorghum bicolor Species Poaceae Eukaryota n.a. seed n.a. PMID[25172742]
NPO20712 Panax quinquefolius Species Araliaceae Eukaryota leaves and stems n.a. n.a. PMID[25442304]
NPO29401 Bupleurum chinense Species Apiaceae Eukaryota roots n.a. n.a. PMID[26259802]
NPO13981 Helianthella quinquenervis Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[8882437]
NPO26371 Sorghum bicolor Species Poaceae Eukaryota n.a. n.a. n.a. PMID[9677276]
NPO29401 Bupleurum chinense Species Apiaceae Eukaryota n.a. n.a. n.a. Database[Article]
NPO26371 Sorghum bicolor Species Poaceae Eukaryota n.a. n.a. Database[FooDB]
NPO29812 Panax quinquefolium Species Araliaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO6528 Myroxylon pereirae Species Fabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO14105.2 Panax pseudo-ginseng var. notoginseng Varieties Araliaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO16662 Plumbago indica Species Plumbaginaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO14148.1 Panax pseudo - ginseng var. notoginseng Varieties Araliaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO16741 Codonopsis pilosula Species Campanulaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO16412 Menyanthes trifoliata Species Menyanthaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO27892 Eupatorium glandulosum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO29401 Bupleurum chinense Species Apiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO20712 Panax quinquefolius Species Araliaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO16741 Codonopsis pilosula Species Campanulaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO26371 Sorghum bicolor Species Poaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO14105.2 Panax pseudo-ginseng var. notoginseng Varieties Araliaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO16412 Menyanthes trifoliata Species Menyanthaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO27892 Eupatorium glandulosum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO16662 Plumbago indica Species Plumbaginaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO6528 Myroxylon pereirae Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO15985 Iris bungei Species Iridaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO29401 Bupleurum chinense Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO16741 Codonopsis pilosula Species Campanulaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO16412 Menyanthes trifoliata Species Menyanthaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO29812 Panax quinquefolium Species Araliaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO29401 Bupleurum chinense Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO6528 Myroxylon pereirae Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO20712 Panax quinquefolius Species Araliaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO29401 Bupleurum chinense Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO16741 Codonopsis pilosula Species Campanulaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO17133 Clathria reinwardti Species Microcionidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3610 Strychnos panganensis Species Loganiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO29401 Bupleurum chinense Species Apiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1871 Aristolochia durior Species Aristolochiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26371 Sorghum bicolor Species Poaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17298 Thamnophis butleri Species Colubridae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16412 Menyanthes trifoliata Species Menyanthaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10414 Gram-negative bacterium n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO16887 Cordyline cannifolia Species Asparagaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20712 Panax quinquefolius Species Araliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16741 Codonopsis pilosula Species Campanulaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14495 Lindheimera texana Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17034 Panagrellus redivivus Species Panagrolaimidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11052 Helianthus hirsutus Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4211 Negombata corticata Species Latrunculiidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13981 Helianthella quinquenervis Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6803 Heterotheca subaxillaris Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14916 Pseudophryne australis Species Myobatrachidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24739 Graphiopsis chlorocephala Species Cladosporiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13479 Flourensia riparia Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10558 Vernonia wildii Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15685 Paspalum dilatatum Species Poaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9379 Cytisus caucasicus Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3703 Achillea ochroleuca Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1178 Delphinium elisabethae Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13995 Siparuna macrotepala Species Siparunaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8889 Senecio gallicus Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27892 Eupatorium glandulosum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16662 Plumbago indica Species Plumbaginaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6115 Primulina dryas Species Gesneriaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15985 Iris bungei Species Iridaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16198 Parmelia quercina Species Parmeliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6528 Myroxylon pereirae Species Fabaceae 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
NPT83 Cell Line MCF7 Homo sapiens ED50 = 29.0 ug ml-1 PMID[547804]
NPT139 Cell Line HT-29 Homo sapiens ED50 = 18.0 ug ml-1 PMID[547804]
NPT81 Cell Line A549 Homo sapiens ED50 = 25.0 ug ml-1 PMID[547804]
NPT140 Organism Artemia Artemia LC50 = 31.0 ug.mL-1 PMID[547804]
NPT117 Organism Echinochloa crus-galli Echinochloa crus-galli IC50 = 6.0 ug.mL-1 PMID[547804]
NPT965 Organism Amaranthus hypochondriacus Amaranthus hypochondriacus IC50 = 7.0 ug.mL-1 PMID[547804]
NPT776 Organism Spodoptera littoralis Spodoptera littoralis FR50 = 0.08 n.a. PMID[547806]
NPT176 Organism Artemia salina Artemia salina LC50 = 0.9 ppm PMID[547806]

☑ 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 NPC229646 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
0.9615 High Similarity NPC46869
0.9542 High Similarity NPC161196
0.947 High Similarity NPC157855
0.947 High Similarity NPC253616
0.9466 High Similarity NPC151113
0.9449 High Similarity NPC473907
0.9403 High Similarity NPC472409
0.9398 High Similarity NPC36414
0.9398 High Similarity NPC17848
0.9394 High Similarity NPC268081
0.9375 High Similarity NPC473894
0.937 High Similarity NPC475496
0.937 High Similarity NPC49852
0.9333 High Similarity NPC103362
0.9328 High Similarity NPC23257
0.9328 High Similarity NPC11566
0.9313 High Similarity NPC247743
0.9313 High Similarity NPC292998
0.9308 High Similarity NPC284424
0.9265 High Similarity NPC226636
0.9265 High Similarity NPC11561
0.9259 High Similarity NPC471587
0.9259 High Similarity NPC475680
0.9259 High Similarity NPC150522
0.9259 High Similarity NPC305355
0.9254 High Similarity NPC470669
0.9254 High Similarity NPC470668
0.9254 High Similarity NPC131130
0.9248 High Similarity NPC174999
0.9248 High Similarity NPC254741
0.9242 High Similarity NPC125920
0.9237 High Similarity NPC473655
0.9237 High Similarity NPC101294
0.9213 High Similarity NPC65041
0.9197 High Similarity NPC17262
0.9197 High Similarity NPC59522
0.9191 High Similarity NPC64908
0.9191 High Similarity NPC118840
0.9191 High Similarity NPC147688
0.9191 High Similarity NPC156590
0.9191 High Similarity NPC205006
0.9191 High Similarity NPC110969
0.9185 High Similarity NPC472515
0.9185 High Similarity NPC473076
0.9179 High Similarity NPC38153
0.9179 High Similarity NPC259685
0.9173 High Similarity NPC60667
0.9173 High Similarity NPC101752
0.9167 High Similarity NPC93756
0.9167 High Similarity NPC108113
0.916 High Similarity NPC278556
0.913 High Similarity NPC234629
0.913 High Similarity NPC179970
0.913 High Similarity NPC311741
0.9124 High Similarity NPC147145
0.9118 High Similarity NPC241100
0.9118 High Similarity NPC270883
0.9118 High Similarity NPC261227
0.9118 High Similarity NPC159275
0.9118 High Similarity NPC172986
0.9118 High Similarity NPC235239
0.9104 High Similarity NPC472516
0.9098 High Similarity NPC125269
0.9077 High Similarity NPC211120
0.9058 High Similarity NPC106985
0.9058 High Similarity NPC166138
0.9058 High Similarity NPC18585
0.9058 High Similarity NPC38219
0.9051 High Similarity NPC282300
0.9051 High Similarity NPC52576
0.9044 High Similarity NPC217186
0.9044 High Similarity NPC55018
0.9044 High Similarity NPC96565
0.9044 High Similarity NPC216978
0.9044 High Similarity NPC78913
0.9044 High Similarity NPC220062
0.9044 High Similarity NPC139554
0.9044 High Similarity NPC18260
0.9044 High Similarity NPC53181
0.9044 High Similarity NPC301217
0.9044 High Similarity NPC303633
0.9037 High Similarity NPC317119
0.903 High Similarity NPC99854
0.9023 High Similarity NPC223354
0.9015 High Similarity NPC31872
0.9015 High Similarity NPC473584
0.9015 High Similarity NPC475589
0.9 High Similarity NPC79469
0.9 High Similarity NPC237635
0.9 High Similarity NPC201731
0.9 High Similarity NPC125887
0.9 High Similarity NPC104406
0.9 High Similarity NPC97716
0.9 High Similarity NPC110303
0.9 High Similarity NPC24673
0.9 High Similarity NPC23728
0.8993 High Similarity NPC209040
0.8993 High Similarity NPC469953
0.8993 High Similarity NPC171656
0.8986 High Similarity NPC217083
0.8986 High Similarity NPC214236
0.8986 High Similarity NPC293852
0.8986 High Similarity NPC162476
0.8986 High Similarity NPC62840
0.8986 High Similarity NPC144499
0.8986 High Similarity NPC59739
0.8986 High Similarity NPC299080
0.8986 High Similarity NPC78803
0.8978 High Similarity NPC470856
0.8978 High Similarity NPC171094
0.8978 High Similarity NPC69769
0.8971 High Similarity NPC21350
0.8971 High Similarity NPC474487
0.8971 High Similarity NPC470672
0.8971 High Similarity NPC470671
0.8971 High Similarity NPC201395
0.8971 High Similarity NPC474504
0.8971 High Similarity NPC124269
0.8963 High Similarity NPC41461
0.8963 High Similarity NPC477243
0.8963 High Similarity NPC240593
0.8963 High Similarity NPC477244
0.8963 High Similarity NPC25287
0.8963 High Similarity NPC472883
0.8963 High Similarity NPC12165
0.8963 High Similarity NPC98115
0.8963 High Similarity NPC168105
0.8963 High Similarity NPC249606
0.8963 High Similarity NPC187826
0.8963 High Similarity NPC66349
0.8963 High Similarity NPC186838
0.8963 High Similarity NPC1486
0.8963 High Similarity NPC156910
0.8963 High Similarity NPC29638
0.8963 High Similarity NPC61546
0.8963 High Similarity NPC72452
0.8963 High Similarity NPC150399
0.8963 High Similarity NPC274109
0.8963 High Similarity NPC477242
0.8955 High Similarity NPC164136
0.8947 High Similarity NPC25937
0.8947 High Similarity NPC10971
0.8947 High Similarity NPC182428
0.8939 High Similarity NPC5515
0.8939 High Similarity NPC270369
0.8936 High Similarity NPC132592
0.8936 High Similarity NPC266572
0.8936 High Similarity NPC6511
0.8936 High Similarity NPC160821
0.8929 High Similarity NPC195621
0.8929 High Similarity NPC301276
0.8929 High Similarity NPC267375
0.8929 High Similarity NPC83357
0.8929 High Similarity NPC67805
0.8929 High Similarity NPC142405
0.8929 High Similarity NPC20488
0.8929 High Similarity NPC111786
0.8929 High Similarity NPC475052
0.8929 High Similarity NPC214774
0.8929 High Similarity NPC124729
0.8929 High Similarity NPC246948
0.8929 High Similarity NPC176229
0.8929 High Similarity NPC88964
0.8929 High Similarity NPC54577
0.8929 High Similarity NPC312973
0.8929 High Similarity NPC477955
0.8929 High Similarity NPC470647
0.8923 High Similarity NPC41721
0.8923 High Similarity NPC37512
0.8921 High Similarity NPC478086
0.8921 High Similarity NPC316816
0.8921 High Similarity NPC310130
0.8921 High Similarity NPC143896
0.8921 High Similarity NPC149026
0.8921 High Similarity NPC255133
0.8921 High Similarity NPC214166
0.8921 High Similarity NPC150408
0.8921 High Similarity NPC91560
0.8921 High Similarity NPC39329
0.8921 High Similarity NPC257097
0.8921 High Similarity NPC219915
0.8921 High Similarity NPC75049
0.8921 High Similarity NPC68104
0.8921 High Similarity NPC242100
0.8921 High Similarity NPC169591
0.8921 High Similarity NPC164980
0.8921 High Similarity NPC221432
0.8921 High Similarity NPC175504
0.8915 High Similarity NPC165556
0.8913 High Similarity NPC22467
0.8913 High Similarity NPC254010
0.8913 High Similarity NPC3188
0.8905 High Similarity NPC262635
0.8905 High Similarity NPC136095
0.8905 High Similarity NPC471697
0.8905 High Similarity NPC137009
0.8905 High Similarity NPC473209
0.8897 High Similarity NPC228661
0.8897 High Similarity NPC332594
0.8897 High Similarity NPC266597

  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 NPC229646 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
0.9248 High Similarity NPD2796 Approved
0.8905 High Similarity NPD1243 Approved
0.8872 High Similarity NPD1240 Approved
0.8857 High Similarity NPD7410 Clinical (unspecified phase)
0.8857 High Similarity NPD4378 Clinical (unspecified phase)
0.8741 High Similarity NPD1607 Approved
0.8714 High Similarity NPD643 Clinical (unspecified phase)
0.8696 High Similarity NPD1549 Phase 2
0.8623 High Similarity NPD1552 Clinical (unspecified phase)
0.8623 High Similarity NPD1550 Clinical (unspecified phase)
0.8613 High Similarity NPD1510 Phase 2
0.8601 High Similarity NPD920 Approved
0.8592 High Similarity NPD642 Clinical (unspecified phase)
0.8521 High Similarity NPD6799 Approved
0.8493 Intermediate Similarity NPD7411 Suspended
0.8435 Intermediate Similarity NPD6801 Discontinued
0.8378 Intermediate Similarity NPD7096 Clinical (unspecified phase)
0.8378 Intermediate Similarity NPD7819 Suspended
0.8299 Intermediate Similarity NPD6599 Discontinued
0.8299 Intermediate Similarity NPD4380 Phase 2
0.8255 Intermediate Similarity NPD2393 Clinical (unspecified phase)
0.8214 Intermediate Similarity NPD3748 Approved
0.8212 Intermediate Similarity NPD7075 Discontinued
0.82 Intermediate Similarity NPD8443 Clinical (unspecified phase)
0.8182 Intermediate Similarity NPD1547 Clinical (unspecified phase)
0.8169 Intermediate Similarity NPD970 Clinical (unspecified phase)
0.8158 Intermediate Similarity NPD919 Approved
0.8138 Intermediate Similarity NPD1511 Approved
0.8112 Intermediate Similarity NPD2800 Approved
0.8112 Intermediate Similarity NPD7421 Clinical (unspecified phase)
0.8105 Intermediate Similarity NPD5494 Approved
0.8071 Intermediate Similarity NPD6651 Approved
0.8052 Intermediate Similarity NPD1247 Approved
0.8047 Intermediate Similarity NPD1241 Discontinued
0.8043 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.8029 Intermediate Similarity NPD6832 Phase 2
0.8027 Intermediate Similarity NPD1512 Approved
0.8013 Intermediate Similarity NPD2801 Approved
0.7986 Intermediate Similarity NPD2654 Approved
0.7974 Intermediate Similarity NPD4381 Clinical (unspecified phase)
0.7961 Intermediate Similarity NPD3817 Phase 2
0.7958 Intermediate Similarity NPD2799 Discontinued
0.7947 Intermediate Similarity NPD1934 Approved
0.7931 Intermediate Similarity NPD3750 Approved
0.7914 Intermediate Similarity NPD1296 Phase 2
0.7908 Intermediate Similarity NPD3882 Suspended
0.7908 Intermediate Similarity NPD7768 Phase 2
0.7902 Intermediate Similarity NPD1551 Phase 2
0.7898 Intermediate Similarity NPD7852 Clinical (unspecified phase)
0.7852 Intermediate Similarity NPD3972 Approved
0.7852 Intermediate Similarity NPD9717 Approved
0.7852 Intermediate Similarity NPD5403 Approved
0.7838 Intermediate Similarity NPD5401 Approved
0.7808 Intermediate Similarity NPD1878 Clinical (unspecified phase)
0.7786 Intermediate Similarity NPD2313 Discontinued
0.7778 Intermediate Similarity NPD422 Phase 1
0.7778 Intermediate Similarity NPD2935 Discontinued
0.7754 Intermediate Similarity NPD2798 Approved
0.7754 Intermediate Similarity NPD1019 Discontinued
0.775 Intermediate Similarity NPD7804 Clinical (unspecified phase)
0.7742 Intermediate Similarity NPD3749 Approved
0.7724 Intermediate Similarity NPD2344 Approved
0.7722 Intermediate Similarity NPD3926 Phase 2
0.7718 Intermediate Similarity NPD2534 Approved
0.7718 Intermediate Similarity NPD2533 Approved
0.7718 Intermediate Similarity NPD2532 Approved
0.7707 Intermediate Similarity NPD6959 Discontinued
0.7681 Intermediate Similarity NPD1203 Approved
0.7654 Intermediate Similarity NPD5953 Discontinued
0.764 Intermediate Similarity NPD7286 Phase 2
0.7578 Intermediate Similarity NPD3818 Discontinued
0.7562 Intermediate Similarity NPD6167 Clinical (unspecified phase)
0.7562 Intermediate Similarity NPD6166 Phase 2
0.7562 Intermediate Similarity NPD6168 Clinical (unspecified phase)
0.7561 Intermediate Similarity NPD4419 Clinical (unspecified phase)
0.7554 Intermediate Similarity NPD3266 Approved
0.7554 Intermediate Similarity NPD3267 Approved
0.7552 Intermediate Similarity NPD3142 Approved
0.7552 Intermediate Similarity NPD4307 Phase 2
0.7552 Intermediate Similarity NPD3140 Approved
0.7534 Intermediate Similarity NPD6100 Approved
0.7534 Intermediate Similarity NPD6099 Approved
0.7518 Intermediate Similarity NPD1008 Clinical (unspecified phase)
0.7517 Intermediate Similarity NPD2309 Approved
0.75 Intermediate Similarity NPD5124 Phase 1
0.75 Intermediate Similarity NPD5123 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD1899 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD5402 Approved
0.75 Intermediate Similarity NPD1933 Approved
0.75 Intermediate Similarity NPD6980 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD17 Approved
0.7485 Intermediate Similarity NPD1729 Discontinued
0.7483 Intermediate Similarity NPD1471 Phase 3
0.7481 Intermediate Similarity NPD9545 Approved
0.7481 Intermediate Similarity NPD1548 Phase 1
0.7468 Intermediate Similarity NPD6585 Discontinued
0.7466 Intermediate Similarity NPD1509 Clinical (unspecified phase)
0.7466 Intermediate Similarity NPD7033 Discontinued
0.7463 Intermediate Similarity NPD9493 Approved
0.7453 Intermediate Similarity NPD2403 Approved
0.745 Intermediate Similarity NPD6398 Clinical (unspecified phase)
0.745 Intermediate Similarity NPD4628 Phase 3
0.7438 Intermediate Similarity NPD6232 Discontinued
0.7431 Intermediate Similarity NPD943 Approved
0.7429 Intermediate Similarity NPD2797 Approved
0.7423 Intermediate Similarity NPD7054 Approved
0.7419 Intermediate Similarity NPD5889 Approved
0.7419 Intermediate Similarity NPD5890 Approved
0.7413 Intermediate Similarity NPD3268 Approved
0.7407 Intermediate Similarity NPD7473 Discontinued
0.7403 Intermediate Similarity NPD3226 Approved
0.7394 Intermediate Similarity NPD6559 Discontinued
0.7378 Intermediate Similarity NPD7472 Approved
0.7378 Intermediate Similarity NPD7074 Phase 3
0.7365 Intermediate Similarity NPD2346 Discontinued
0.7357 Intermediate Similarity NPD1876 Approved
0.7347 Intermediate Similarity NPD4308 Phase 3
0.7342 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.7338 Intermediate Similarity NPD1608 Approved
0.7333 Intermediate Similarity NPD6797 Phase 2
0.7317 Intermediate Similarity NPD5844 Phase 1
0.7299 Intermediate Similarity NPD1651 Approved
0.7292 Intermediate Similarity NPD411 Approved
0.7292 Intermediate Similarity NPD4907 Clinical (unspecified phase)
0.7289 Intermediate Similarity NPD7251 Discontinued
0.7289 Intermediate Similarity NPD6104 Discontinued
0.7285 Intermediate Similarity NPD3887 Approved
0.7266 Intermediate Similarity NPD1610 Phase 2
0.7261 Intermediate Similarity NPD6280 Approved
0.7261 Intermediate Similarity NPD6279 Approved
0.726 Intermediate Similarity NPD447 Suspended
0.7256 Intermediate Similarity NPD7893 Clinical (unspecified phase)
0.7248 Intermediate Similarity NPD2353 Approved
0.7248 Intermediate Similarity NPD2355 Clinical (unspecified phase)
0.7246 Intermediate Similarity NPD7808 Phase 3
0.7239 Intermediate Similarity NPD7784 Clinical (unspecified phase)
0.7218 Intermediate Similarity NPD1609 Clinical (unspecified phase)
0.7171 Intermediate Similarity NPD3295 Clinical (unspecified phase)
0.717 Intermediate Similarity NPD4288 Approved
0.7154 Intermediate Similarity NPD9697 Approved
0.7153 Intermediate Similarity NPD4908 Phase 1
0.7143 Intermediate Similarity NPD4661 Approved
0.7143 Intermediate Similarity NPD8090 Clinical (unspecified phase)
0.7143 Intermediate Similarity NPD4338 Clinical (unspecified phase)
0.7143 Intermediate Similarity NPD230 Phase 1
0.7143 Intermediate Similarity NPD4662 Approved
0.7133 Intermediate Similarity NPD2343 Clinical (unspecified phase)
0.7132 Intermediate Similarity NPD9261 Approved
0.7126 Intermediate Similarity NPD4363 Phase 3
0.7126 Intermediate Similarity NPD4360 Phase 2
0.7117 Intermediate Similarity NPD5710 Approved
0.7117 Intermediate Similarity NPD5711 Approved
0.7113 Intermediate Similarity NPD3225 Approved
0.7103 Intermediate Similarity NPD4625 Phase 3
0.7097 Intermediate Similarity NPD5049 Phase 3
0.7089 Intermediate Similarity NPD7615 Clinical (unspecified phase)
0.7086 Intermediate Similarity NPD4361 Phase 2
0.7086 Intermediate Similarity NPD2424 Discontinued
0.7086 Intermediate Similarity NPD4362 Clinical (unspecified phase)
0.7078 Intermediate Similarity NPD7390 Discontinued
0.7063 Intermediate Similarity NPD1164 Approved
0.7059 Intermediate Similarity NPD2354 Approved
0.705 Intermediate Similarity NPD5691 Approved
0.705 Intermediate Similarity NPD4196 Clinical (unspecified phase)
0.7042 Intermediate Similarity NPD4749 Approved
0.7039 Intermediate Similarity NPD1652 Phase 2
0.7021 Intermediate Similarity NPD1281 Approved
0.7012 Intermediate Similarity NPD6808 Phase 2
0.7 Intermediate Similarity NPD651 Clinical (unspecified phase)
0.7 Intermediate Similarity NPD1778 Approved
0.7 Intermediate Similarity NPD1465 Phase 2
0.6993 Remote Similarity NPD7003 Approved
0.697 Remote Similarity NPD3134 Approved
0.6962 Remote Similarity NPD7458 Discontinued
0.6957 Remote Similarity NPD2296 Approved
0.6954 Remote Similarity NPD4477 Approved
0.6954 Remote Similarity NPD4476 Approved
0.6943 Remote Similarity NPD5586 Clinical (unspecified phase)
0.6939 Remote Similarity NPD6410 Clinical (unspecified phase)
0.6939 Remote Similarity NPD6798 Discontinued
0.6923 Remote Similarity NPD7993 Clinical (unspecified phase)
0.6917 Remote Similarity NPD9264 Approved
0.6917 Remote Similarity NPD1358 Approved
0.6917 Remote Similarity NPD9263 Approved
0.6917 Remote Similarity NPD9267 Approved
0.6912 Remote Similarity NPD5535 Approved
0.6909 Remote Similarity NPD7229 Phase 3
0.6901 Remote Similarity NPD1201 Approved
0.6885 Remote Similarity NPD7584 Approved
0.6879 Remote Similarity NPD2186 Approved
0.6879 Remote Similarity NPD4626 Approved
0.6875 Remote Similarity NPD1283 Approved
0.6867 Remote Similarity NPD5242 Approved
0.6866 Remote Similarity NPD9266 Approved
0.6866 Remote Similarity NPD2684 Approved
0.6866 Remote Similarity NPD74 Approved
0.6857 Remote Similarity NPD1894 Discontinued
0.6855 Remote Similarity NPD5808 Clinical (unspecified phase)
0.6852 Remote Similarity NPD5353 Approved
0.6849 Remote Similarity NPD9494 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