Structure

Physi-Chem Properties

Molecular Weight:  330.18
Volume:  338.945
LogP:  3.728
LogD:  3.319
LogS:  -4.387
# Rotatable Bonds:  1
TPSA:  66.13
# H-Bond Aceptor:  4
# H-Bond Donor:  2
# Rings:  5
# Heavy Atoms:  4

MedChem Properties

QED Drug-Likeness Score:  0.753
Synthetic Accessibility Score:  5.314
Fsp3:  0.7
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Rejected
GSK Rule:  Accepted
BMS Rule:  1
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.947
MDCK Permeability:  1.9863276975229383e-05
Pgp-inhibitor:  0.006
Pgp-substrate:  0.127
Human Intestinal Absorption (HIA):  0.008
20% Bioavailability (F20%):  0.006
30% Bioavailability (F30%):  0.014

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.213
Plasma Protein Binding (PPB):  95.3823013305664%
Volume Distribution (VD):  1.672
Pgp-substrate:  6.6964521408081055%

ADMET: Metabolism

CYP1A2-inhibitor:  0.043
CYP1A2-substrate:  0.896
CYP2C19-inhibitor:  0.027
CYP2C19-substrate:  0.838
CYP2C9-inhibitor:  0.294
CYP2C9-substrate:  0.536
CYP2D6-inhibitor:  0.015
CYP2D6-substrate:  0.453
CYP3A4-inhibitor:  0.183
CYP3A4-substrate:  0.399

ADMET: Excretion

Clearance (CL):  9.43
Half-life (T1/2):  0.768

ADMET: Toxicity

hERG Blockers:  0.139
Human Hepatotoxicity (H-HT):  0.689
Drug-inuced Liver Injury (DILI):  0.609
AMES Toxicity:  0.795
Rat Oral Acute Toxicity:  0.946
Maximum Recommended Daily Dose:  0.919
Skin Sensitization:  0.759
Carcinogencity:  0.804
Eye Corrosion:  0.004
Eye Irritation:  0.027
Respiratory Toxicity:  0.968

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

  Natural Product: NPC81630

Natural Product ID:  NPC81630
Common Name*:   DIJWCRKTZVUBDY-PHJMNMFVSA-N
IUPAC Name:   n.a.
Synonyms:  
Standard InCHIKey:  DIJWCRKTZVUBDY-PHJMNMFVSA-N
Standard InCHI:  InChI=1S/C20H26O4/c1-18(2)6-4-7-19(3)13(18)5-8-20-14(19)9-12-15(16(20)24-20)11(10-21)17(22)23-12/h9,13-14,16,21H,4-8,10H2,1-3H3/t13-,14+,16-,19-,20+/m1/s1
SMILES:  CC1(C)CCC[C@]2(C)[C@@H]1CC[C@]13[C@H]2C=C2C(=C(CO)C(=O)O2)[C@H]1O3
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL1988221
PubChem CID:   6712606
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000002] Organoheterocyclic compounds
      • [CHEMONTID:0001634] Naphthofurans

*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
NPO10031 Euphorbia antiquorum Species Euphorbiaceae Eukaryota n.a. n.a. n.a. PMID[11858748]
NPO16205 Euphorbia fischeriana Species Euphorbiaceae Eukaryota roots n.a. n.a. PMID[16792421]
NPO16205 Euphorbia fischeriana Species Euphorbiaceae Eukaryota n.a. whole plant n.a. PMID[21534540]
NPO16205 Euphorbia fischeriana Species Euphorbiaceae Eukaryota whole plants Panshi, Jilin Province, China 2009-JUN PMID[21534540]
NPO299 Euphorbia ebracteolata Species Euphorbiaceae Eukaryota roots n.a. n.a. PMID[24660966]
NPO10031 Euphorbia antiquorum Species Euphorbiaceae Eukaryota n.a. n.a. n.a. PMID[24840014]
NPO16205 Euphorbia fischeriana Species Euphorbiaceae Eukaryota n.a. n.a. n.a. PMID[25453801]
NPO16205 Euphorbia fischeriana Species Euphorbiaceae Eukaryota n.a. n.a. n.a. PMID[26702644]
NPO16205 Euphorbia fischeriana Species Euphorbiaceae Eukaryota Roots n.a. n.a. PMID[28383891]
NPO299 Euphorbia ebracteolata Species Euphorbiaceae Eukaryota Roots n.a. n.a. PMID[29148766]
NPO10031 Euphorbia antiquorum Species Euphorbiaceae Eukaryota Stems n.a. n.a. PMID[31180680]
NPO299 Euphorbia ebracteolata Species Euphorbiaceae Eukaryota n.a. n.a. n.a. PMID[31184480]
NPO8770 Euphorbia wallichii Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO16205 Euphorbia fischeriana Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO10031 Euphorbia antiquorum Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO16205 Euphorbia fischeriana Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO8770 Euphorbia wallichii Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO10031 Euphorbia antiquorum Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO299 Euphorbia ebracteolata Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO299 Euphorbia ebracteolata Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO16205 Euphorbia fischeriana Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO299 Euphorbia ebracteolata Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO16205 Euphorbia fischeriana Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10031 Euphorbia antiquorum Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8770 Euphorbia wallichii Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO299 Euphorbia ebracteolata Species Euphorbiaceae 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
NPT367 Cell Line MDA-N Homo sapiens GI50 n.a. 14028.14 nM PMID[493193]
NPT368 Cell Line SN12C Homo sapiens GI50 n.a. 12941.96 nM PMID[493193]
NPT369 Cell Line ACHN Homo sapiens GI50 n.a. 29174.27 nM PMID[493193]
NPT370 Cell Line NCI-H23 Homo sapiens GI50 n.a. 17538.81 nM PMID[493193]
NPT372 Cell Line HOP-92 Homo sapiens GI50 n.a. 15381.55 nM PMID[493193]
NPT371 Cell Line UO-31 Homo sapiens GI50 n.a. 11721.95 nM PMID[493193]
NPT90 Cell Line DU-145 Homo sapiens GI50 n.a. 18407.72 nM PMID[493193]
NPT373 Cell Line SK-MEL-5 Homo sapiens GI50 n.a. 15523.87 nM PMID[493193]
NPT375 Cell Line Malme-3M Homo sapiens GI50 n.a. 1101.54 nM PMID[493193]
NPT111 Cell Line K562 Homo sapiens GI50 n.a. 21428.91 nM PMID[493193]
NPT376 Cell Line A498 Homo sapiens GI50 n.a. 27164.39 nM PMID[493193]
NPT112 Cell Line MOLT-4 Homo sapiens GI50 n.a. 17298.16 nM PMID[493193]
NPT378 Cell Line NCI/ADR-RES Homo sapiens GI50 n.a. 15848.93 nM PMID[493193]
NPT379 Cell Line HOP-62 Homo sapiens GI50 n.a. 25585.86 nM PMID[493193]
NPT380 Cell Line U-251 Homo sapiens GI50 n.a. 24434.31 nM PMID[493193]
NPT382 Cell Line OVCAR-5 Homo sapiens GI50 n.a. 9705.1 nM PMID[493193]
NPT82 Cell Line MDA-MB-231 Homo sapiens GI50 n.a. 31117.16 nM PMID[493193]
NPT383 Cell Line SNB-19 Homo sapiens GI50 n.a. 13614.45 nM PMID[493193]
NPT384 Cell Line TK-10 Homo sapiens GI50 n.a. 25234.81 nM PMID[493193]
NPT323 Cell Line SW-620 Homo sapiens GI50 n.a. 18923.44 nM PMID[493193]
NPT386 Cell Line KM12 Homo sapiens GI50 n.a. 11939.88 nM PMID[493193]
NPT455 Cell Line NCI-H522 Homo sapiens GI50 n.a. 10069.32 nM PMID[493193]
NPT388 Cell Line NCI-H322M Homo sapiens GI50 n.a. 19724.23 nM PMID[493193]
NPT387 Cell Line M14 Homo sapiens GI50 n.a. 15776.11 nM PMID[493193]
NPT389 Cell Line RPMI-8226 Homo sapiens GI50 n.a. 21134.89 nM PMID[493193]
NPT456 Cell Line OVCAR-4 Homo sapiens GI50 n.a. 19230.92 nM PMID[493193]
NPT457 Cell Line BT-549 Homo sapiens GI50 n.a. 21978.6 nM PMID[493193]
NPT147 Cell Line SK-MEL-2 Homo sapiens GI50 n.a. 22803.42 nM PMID[493193]
NPT391 Cell Line HCC 2998 Homo sapiens GI50 n.a. 18923.44 nM PMID[493193]
NPT81 Cell Line A549 Homo sapiens GI50 n.a. 10423.17 nM PMID[493193]
NPT392 Cell Line SNB-75 Homo sapiens GI50 n.a. 30478.95 nM PMID[493193]
NPT393 Cell Line HCT-116 Homo sapiens GI50 n.a. 1438.8 nM PMID[493193]
NPT148 Cell Line HCT-15 Homo sapiens GI50 n.a. 14421.15 nM PMID[493193]
NPT394 Cell Line EKVX Homo sapiens GI50 n.a. 13899.53 nM PMID[493193]
NPT395 Cell Line SF-268 Homo sapiens GI50 n.a. 15170.5 nM PMID[493193]
NPT83 Cell Line MCF7 Homo sapiens GI50 n.a. 26363.31 nM PMID[493193]
NPT306 Cell Line PC-3 Homo sapiens GI50 n.a. 14927.94 nM PMID[493193]
NPT146 Cell Line SK-OV-3 Homo sapiens GI50 n.a. 20558.91 nM PMID[493193]
NPT397 Cell Line NCI-H460 Homo sapiens GI50 n.a. 18238.96 nM PMID[493193]
NPT398 Cell Line UACC-62 Homo sapiens GI50 n.a. 13489.63 nM PMID[493193]
NPT308 Cell Line CAKI-1 Homo sapiens GI50 n.a. 18793.17 nM PMID[493193]
NPT399 Cell Line SF-295 Homo sapiens GI50 n.a. 16943.38 nM PMID[493193]
NPT400 Cell Line MDA-MB-435 Homo sapiens GI50 n.a. 20464.45 nM PMID[493193]
NPT458 Cell Line IGROV-1 Homo sapiens GI50 n.a. 5675.45 nM PMID[493193]
NPT401 Cell Line 786-0 Homo sapiens GI50 n.a. 14288.94 nM PMID[493193]
NPT403 Cell Line UACC-257 Homo sapiens GI50 n.a. 18155.16 nM PMID[493193]
NPT139 Cell Line HT-29 Homo sapiens GI50 n.a. 13995.87 nM PMID[493193]
NPT405 Cell Line NCI-H226 Homo sapiens GI50 n.a. 15667.51 nM PMID[493193]
NPT170 Cell Line SK-MEL-28 Homo sapiens GI50 n.a. 16634.13 nM PMID[493193]
NPT406 Cell Line RXF 393 Homo sapiens GI50 n.a. 19906.73 nM PMID[493193]
NPT407 Cell Line COLO 205 Homo sapiens GI50 n.a. 16481.62 nM PMID[493193]
NPT34 Cell Line BV-2 Mus musculus IC50 = 9100.0 nM PMID[493195]
NPT82 Cell Line MDA-MB-231 Homo sapiens IC50 = 8800.0 nM PMID[493196]
NPT148 Cell Line HCT-15 Homo sapiens IC50 = 13000.0 nM PMID[493196]
NPT602 Organism Mycobacterium smegmatis Mycobacterium smegmatis MIC = 100.0 ug.mL-1 PMID[493194]
NPT23295 CELL-LINE LNCaP C4-2B Homo sapiens IC50 = 2200.0 nM PMID[493196]

☑ 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 NPC81630 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
0.9175 High Similarity NPC260796
0.8614 High Similarity NPC278673
0.85 High Similarity NPC111273
0.8491 Intermediate Similarity NPC50124
0.8476 Intermediate Similarity NPC471206
0.8469 Intermediate Similarity NPC280149
0.8469 Intermediate Similarity NPC221111
0.8462 Intermediate Similarity NPC471938
0.8416 Intermediate Similarity NPC16967
0.84 Intermediate Similarity NPC191521
0.8381 Intermediate Similarity NPC471937
0.8365 Intermediate Similarity NPC109195
0.8365 Intermediate Similarity NPC475038
0.8365 Intermediate Similarity NPC471914
0.835 Intermediate Similarity NPC16601
0.8317 Intermediate Similarity NPC276110
0.8302 Intermediate Similarity NPC34768
0.83 Intermediate Similarity NPC162615
0.83 Intermediate Similarity NPC205034
0.83 Intermediate Similarity NPC152778
0.8286 Intermediate Similarity NPC474822
0.8283 Intermediate Similarity NPC78973
0.8182 Intermediate Similarity NPC42658
0.8173 Intermediate Similarity NPC38855
0.8173 Intermediate Similarity NPC474012
0.8173 Intermediate Similarity NPC476299
0.8165 Intermediate Similarity NPC478209
0.8142 Intermediate Similarity NPC478205
0.8142 Intermediate Similarity NPC478206
0.8142 Intermediate Similarity NPC108581
0.8137 Intermediate Similarity NPC471915
0.8137 Intermediate Similarity NPC472441
0.8113 Intermediate Similarity NPC45897
0.81 Intermediate Similarity NPC310479
0.81 Intermediate Similarity NPC182136
0.8081 Intermediate Similarity NPC93411
0.8061 Intermediate Similarity NPC131813
0.8058 Intermediate Similarity NPC165632
0.8058 Intermediate Similarity NPC242848
0.8058 Intermediate Similarity NPC473153
0.8056 Intermediate Similarity NPC179380
0.8056 Intermediate Similarity NPC475074
0.8053 Intermediate Similarity NPC478204
0.8039 Intermediate Similarity NPC105490
0.8019 Intermediate Similarity NPC476081
0.7982 Intermediate Similarity NPC181994
0.7946 Intermediate Similarity NPC171126
0.7946 Intermediate Similarity NPC122056
0.7946 Intermediate Similarity NPC478212
0.7944 Intermediate Similarity NPC23584
0.7941 Intermediate Similarity NPC53555
0.7941 Intermediate Similarity NPC7349
0.7941 Intermediate Similarity NPC472641
0.7941 Intermediate Similarity NPC472812
0.7941 Intermediate Similarity NPC472640
0.7925 Intermediate Similarity NPC11974
0.7921 Intermediate Similarity NPC472642
0.7909 Intermediate Similarity NPC299590
0.7909 Intermediate Similarity NPC75389
0.7909 Intermediate Similarity NPC228477
0.7909 Intermediate Similarity NPC137911
0.7905 Intermediate Similarity NPC474440
0.7905 Intermediate Similarity NPC275086
0.7905 Intermediate Similarity NPC124512
0.7905 Intermediate Similarity NPC159763
0.7905 Intermediate Similarity NPC316598
0.7905 Intermediate Similarity NPC325229
0.7905 Intermediate Similarity NPC278386
0.7895 Intermediate Similarity NPC469684
0.7895 Intermediate Similarity NPC53396
0.7895 Intermediate Similarity NPC98249
0.789 Intermediate Similarity NPC302788
0.789 Intermediate Similarity NPC67321
0.789 Intermediate Similarity NPC43063
0.789 Intermediate Similarity NPC471205
0.789 Intermediate Similarity NPC187435
0.789 Intermediate Similarity NPC79298
0.7885 Intermediate Similarity NPC194132
0.7885 Intermediate Similarity NPC209297
0.7885 Intermediate Similarity NPC190713
0.7885 Intermediate Similarity NPC475380
0.7864 Intermediate Similarity NPC470255
0.7864 Intermediate Similarity NPC140277
0.7857 Intermediate Similarity NPC44537
0.785 Intermediate Similarity NPC11956
0.785 Intermediate Similarity NPC472552
0.7843 Intermediate Similarity NPC472811
0.7843 Intermediate Similarity NPC72845
0.7843 Intermediate Similarity NPC78594
0.7843 Intermediate Similarity NPC329842
0.7838 Intermediate Similarity NPC12795
0.7838 Intermediate Similarity NPC177047
0.783 Intermediate Similarity NPC117685
0.783 Intermediate Similarity NPC324841
0.7826 Intermediate Similarity NPC709
0.7826 Intermediate Similarity NPC284707
0.7826 Intermediate Similarity NPC50774
0.7822 Intermediate Similarity NPC16265
0.7818 Intermediate Similarity NPC90946
0.7818 Intermediate Similarity NPC275060
0.7818 Intermediate Similarity NPC300614
0.781 Intermediate Similarity NPC205143
0.781 Intermediate Similarity NPC121402
0.781 Intermediate Similarity NPC73911
0.781 Intermediate Similarity NPC151681
0.781 Intermediate Similarity NPC132753
0.781 Intermediate Similarity NPC99726
0.781 Intermediate Similarity NPC287668
0.781 Intermediate Similarity NPC475446
0.781 Intermediate Similarity NPC51499
0.781 Intermediate Similarity NPC53844
0.781 Intermediate Similarity NPC175351
0.781 Intermediate Similarity NPC224356
0.781 Intermediate Similarity NPC141401
0.781 Intermediate Similarity NPC311241
0.781 Intermediate Similarity NPC199099
0.781 Intermediate Similarity NPC100912
0.78 Intermediate Similarity NPC166857
0.7798 Intermediate Similarity NPC295843
0.7798 Intermediate Similarity NPC266570
0.7798 Intermediate Similarity NPC477090
0.7798 Intermediate Similarity NPC478208
0.7798 Intermediate Similarity NPC478052
0.7788 Intermediate Similarity NPC476519
0.7788 Intermediate Similarity NPC475966
0.7778 Intermediate Similarity NPC159533
0.7778 Intermediate Similarity NPC120321
0.7778 Intermediate Similarity NPC329345
0.7778 Intermediate Similarity NPC475526
0.7778 Intermediate Similarity NPC297617
0.7778 Intermediate Similarity NPC473283
0.7768 Intermediate Similarity NPC469656
0.7768 Intermediate Similarity NPC474846
0.7768 Intermediate Similarity NPC469655
0.7768 Intermediate Similarity NPC474315
0.7767 Intermediate Similarity NPC472954
0.7767 Intermediate Similarity NPC110022
0.7767 Intermediate Similarity NPC115021
0.7767 Intermediate Similarity NPC139692
0.7759 Intermediate Similarity NPC35171
0.7759 Intermediate Similarity NPC213761
0.7757 Intermediate Similarity NPC244456
0.7757 Intermediate Similarity NPC472554
0.7757 Intermediate Similarity NPC469657
0.7755 Intermediate Similarity NPC311070
0.7748 Intermediate Similarity NPC475065
0.7748 Intermediate Similarity NPC31522
0.7739 Intermediate Similarity NPC183580
0.7739 Intermediate Similarity NPC140055
0.7739 Intermediate Similarity NPC470492
0.7739 Intermediate Similarity NPC286528
0.7739 Intermediate Similarity NPC58662
0.7739 Intermediate Similarity NPC470493
0.7739 Intermediate Similarity NPC157380
0.7739 Intermediate Similarity NPC312824
0.7739 Intermediate Similarity NPC20302
0.7739 Intermediate Similarity NPC243065
0.7739 Intermediate Similarity NPC167606
0.7739 Intermediate Similarity NPC185287
0.7736 Intermediate Similarity NPC218107
0.7736 Intermediate Similarity NPC107806
0.7736 Intermediate Similarity NPC92275
0.7736 Intermediate Similarity NPC181147
0.7736 Intermediate Similarity NPC72647
0.7727 Intermediate Similarity NPC330011
0.7727 Intermediate Similarity NPC329048
0.7727 Intermediate Similarity NPC473284
0.7727 Intermediate Similarity NPC122816
0.7714 Intermediate Similarity NPC162346
0.7714 Intermediate Similarity NPC195366
0.7714 Intermediate Similarity NPC154526
0.7714 Intermediate Similarity NPC472363
0.7714 Intermediate Similarity NPC234993
0.7714 Intermediate Similarity NPC114743
0.7714 Intermediate Similarity NPC472362
0.7714 Intermediate Similarity NPC57664
0.7714 Intermediate Similarity NPC134072
0.7706 Intermediate Similarity NPC472822
0.7706 Intermediate Similarity NPC200861
0.7699 Intermediate Similarity NPC269530
0.7692 Intermediate Similarity NPC279410
0.7692 Intermediate Similarity NPC474370
0.7692 Intermediate Similarity NPC119562
0.7692 Intermediate Similarity NPC104925
0.7692 Intermediate Similarity NPC57117
0.7692 Intermediate Similarity NPC298973
0.7692 Intermediate Similarity NPC469697
0.7692 Intermediate Similarity NPC161998
0.7692 Intermediate Similarity NPC112936
0.7692 Intermediate Similarity NPC38830
0.7685 Intermediate Similarity NPC273005
0.7685 Intermediate Similarity NPC114540
0.7685 Intermediate Similarity NPC32577
0.7685 Intermediate Similarity NPC469606
0.7685 Intermediate Similarity NPC31058
0.7685 Intermediate Similarity NPC165250
0.7685 Intermediate Similarity NPC273668
0.7685 Intermediate Similarity NPC155332
0.7679 Intermediate Similarity NPC478211
0.7679 Intermediate Similarity NPC103491

  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 NPC81630 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
0.7909 Intermediate Similarity NPD4061 Clinical (unspecified phase)
0.7905 Intermediate Similarity NPD4225 Approved
0.7739 Intermediate Similarity NPD7115 Discovery
0.7679 Intermediate Similarity NPD5955 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD7639 Approved
0.75 Intermediate Similarity NPD7640 Approved
0.7411 Intermediate Similarity NPD5954 Clinical (unspecified phase)
0.7407 Intermediate Similarity NPD7638 Approved
0.7339 Intermediate Similarity NPD6648 Approved
0.7273 Intermediate Similarity NPD5344 Discontinued
0.717 Intermediate Similarity NPD7637 Suspended
0.7083 Intermediate Similarity NPD7328 Approved
0.7083 Intermediate Similarity NPD7327 Approved
0.7054 Intermediate Similarity NPD7632 Discontinued
0.7049 Intermediate Similarity NPD7503 Approved
0.7025 Intermediate Similarity NPD7516 Approved
0.7018 Intermediate Similarity NPD7128 Approved
0.7018 Intermediate Similarity NPD5739 Approved
0.7018 Intermediate Similarity NPD6402 Approved
0.7018 Intermediate Similarity NPD6675 Approved
0.6957 Remote Similarity NPD5701 Approved
0.6957 Remote Similarity NPD5697 Approved
0.6897 Remote Similarity NPD6899 Approved
0.6897 Remote Similarity NPD6881 Approved
0.6897 Remote Similarity NPD7320 Approved
0.6881 Remote Similarity NPD7748 Approved
0.6852 Remote Similarity NPD6411 Approved
0.6852 Remote Similarity NPD7515 Phase 2
0.6847 Remote Similarity NPD7902 Approved
0.6838 Remote Similarity NPD6014 Approved
0.6838 Remote Similarity NPD6012 Approved
0.6838 Remote Similarity NPD6373 Approved
0.6838 Remote Similarity NPD6372 Approved
0.6838 Remote Similarity NPD6013 Approved
0.6827 Remote Similarity NPD6400 Clinical (unspecified phase)
0.6827 Remote Similarity NPD7338 Clinical (unspecified phase)
0.6814 Remote Similarity NPD4159 Approved
0.6797 Remote Similarity NPD7319 Approved
0.6796 Remote Similarity NPD4752 Clinical (unspecified phase)
0.6789 Remote Similarity NPD5779 Approved
0.6789 Remote Similarity NPD6399 Phase 3
0.6789 Remote Similarity NPD5778 Approved
0.678 Remote Similarity NPD6883 Approved
0.678 Remote Similarity NPD7290 Approved
0.678 Remote Similarity NPD7102 Approved
0.6774 Remote Similarity NPD8296 Approved
0.6774 Remote Similarity NPD8033 Approved
0.6774 Remote Similarity NPD8335 Approved
0.6774 Remote Similarity NPD8379 Approved
0.6774 Remote Similarity NPD8380 Approved
0.6774 Remote Similarity NPD8378 Approved
0.6754 Remote Similarity NPD5211 Phase 2
0.6752 Remote Similarity NPD6686 Approved
0.6752 Remote Similarity NPD5345 Clinical (unspecified phase)
0.6752 Remote Similarity NPD6011 Approved
0.6731 Remote Similarity NPD6695 Phase 3
0.6724 Remote Similarity NPD6008 Approved
0.6723 Remote Similarity NPD6847 Approved
0.6723 Remote Similarity NPD6617 Approved
0.6723 Remote Similarity NPD8130 Phase 1
0.6723 Remote Similarity NPD6869 Approved
0.6723 Remote Similarity NPD6649 Approved
0.6723 Remote Similarity NPD6650 Approved
0.6698 Remote Similarity NPD3618 Phase 1
0.6696 Remote Similarity NPD6084 Phase 2
0.6696 Remote Similarity NPD4755 Approved
0.6696 Remote Similarity NPD6083 Phase 2
0.6694 Remote Similarity NPD8377 Approved
0.6694 Remote Similarity NPD8294 Approved
0.6667 Remote Similarity NPD5764 Clinical (unspecified phase)
0.6667 Remote Similarity NPD6101 Approved
0.6667 Remote Similarity NPD6053 Discontinued
0.6667 Remote Similarity NPD8297 Approved
0.6667 Remote Similarity NPD6882 Approved
0.6667 Remote Similarity NPD6051 Approved
0.6638 Remote Similarity NPD5141 Approved
0.6636 Remote Similarity NPD4202 Approved
0.6606 Remote Similarity NPD7838 Discovery
0.6604 Remote Similarity NPD1696 Phase 3
0.6604 Remote Similarity NPD1694 Approved
0.6602 Remote Similarity NPD7525 Registered
0.6583 Remote Similarity NPD6401 Clinical (unspecified phase)
0.6579 Remote Similarity NPD5286 Approved
0.6579 Remote Similarity NPD4696 Approved
0.6579 Remote Similarity NPD5285 Approved
0.6579 Remote Similarity NPD4700 Approved
0.6577 Remote Similarity NPD7900 Approved
0.6577 Remote Similarity NPD7901 Clinical (unspecified phase)
0.6562 Remote Similarity NPD7507 Approved
0.656 Remote Similarity NPD6319 Approved
0.6542 Remote Similarity NPD3574 Clinical (unspecified phase)
0.6518 Remote Similarity NPD5695 Phase 3
0.6514 Remote Similarity NPD5328 Approved
0.6514 Remote Similarity NPD7285 Clinical (unspecified phase)
0.6505 Remote Similarity NPD7645 Phase 2
0.6504 Remote Similarity NPD6274 Approved
0.6491 Remote Similarity NPD5696 Approved
0.6481 Remote Similarity NPD7750 Discontinued
0.6481 Remote Similarity NPD7524 Approved
0.6476 Remote Similarity NPD3667 Approved
0.6466 Remote Similarity NPD4633 Approved
0.6466 Remote Similarity NPD5225 Approved
0.6466 Remote Similarity NPD5224 Approved
0.6466 Remote Similarity NPD5226 Approved
0.6442 Remote Similarity NPD6931 Approved
0.6442 Remote Similarity NPD6930 Phase 2
0.641 Remote Similarity NPD5175 Approved
0.641 Remote Similarity NPD5174 Approved
0.6396 Remote Similarity NPD6079 Approved
0.6396 Remote Similarity NPD5281 Approved
0.6396 Remote Similarity NPD5693 Phase 1
0.6396 Remote Similarity NPD5284 Approved
0.6389 Remote Similarity NPD6684 Approved
0.6389 Remote Similarity NPD7146 Approved
0.6389 Remote Similarity NPD7521 Approved
0.6389 Remote Similarity NPD6409 Approved
0.6389 Remote Similarity NPD7334 Approved
0.6389 Remote Similarity NPD5330 Approved
0.6379 Remote Similarity NPD5223 Approved
0.6378 Remote Similarity NPD8513 Phase 3
0.6378 Remote Similarity NPD8515 Approved
0.6378 Remote Similarity NPD8517 Approved
0.6378 Remote Similarity NPD8516 Approved
0.6373 Remote Similarity NPD3701 Clinical (unspecified phase)
0.6372 Remote Similarity NPD6356 Clinical (unspecified phase)
0.6372 Remote Similarity NPD1698 Clinical (unspecified phase)
0.6364 Remote Similarity NPD4753 Phase 2
0.6364 Remote Similarity NPD6371 Approved
0.6364 Remote Similarity NPD4634 Approved
0.6357 Remote Similarity NPD7492 Approved
0.6355 Remote Similarity NPD4786 Approved
0.6355 Remote Similarity NPD3666 Approved
0.6355 Remote Similarity NPD3665 Phase 1
0.6355 Remote Similarity NPD3133 Approved
0.6349 Remote Similarity NPD7100 Approved
0.6349 Remote Similarity NPD7101 Approved
0.6346 Remote Similarity NPD6929 Approved
0.6341 Remote Similarity NPD4632 Approved
0.633 Remote Similarity NPD3573 Approved
0.633 Remote Similarity NPD4751 Clinical (unspecified phase)
0.6321 Remote Similarity NPD5209 Approved
0.632 Remote Similarity NPD6317 Approved
0.6316 Remote Similarity NPD5222 Approved
0.6316 Remote Similarity NPD4697 Phase 3
0.6316 Remote Similarity NPD5221 Approved
0.6316 Remote Similarity NPD5220 Clinical (unspecified phase)
0.6308 Remote Similarity NPD6616 Approved
0.6306 Remote Similarity NPD46 Approved
0.6306 Remote Similarity NPD6698 Approved
0.6306 Remote Similarity NPD5785 Approved
0.6303 Remote Similarity NPD4768 Approved
0.6303 Remote Similarity NPD4767 Approved
0.6299 Remote Similarity NPD6054 Approved
0.6299 Remote Similarity NPD6059 Approved
0.6286 Remote Similarity NPD7514 Phase 3
0.6286 Remote Similarity NPD7332 Phase 2
0.6275 Remote Similarity NPD6942 Approved
0.6275 Remote Similarity NPD8264 Approved
0.6275 Remote Similarity NPD7339 Approved
0.6273 Remote Similarity NPD7513 Clinical (unspecified phase)
0.6273 Remote Similarity NPD6672 Approved
0.6273 Remote Similarity NPD5737 Approved
0.6273 Remote Similarity NPD6903 Approved
0.6271 Remote Similarity NPD4754 Approved
0.627 Remote Similarity NPD6335 Approved
0.627 Remote Similarity NPD6313 Approved
0.627 Remote Similarity NPD6314 Approved
0.6261 Remote Similarity NPD5173 Approved
0.626 Remote Similarity NPD7078 Approved
0.626 Remote Similarity NPD8293 Discontinued
0.625 Remote Similarity NPD6909 Approved
0.625 Remote Similarity NPD6908 Approved
0.625 Remote Similarity NPD8035 Phase 2
0.625 Remote Similarity NPD6016 Approved
0.625 Remote Similarity NPD7087 Discontinued
0.625 Remote Similarity NPD6015 Approved
0.625 Remote Similarity NPD8034 Phase 2
0.6239 Remote Similarity NPD4623 Approved
0.6239 Remote Similarity NPD5279 Phase 3
0.6239 Remote Similarity NPD4519 Discontinued
0.6226 Remote Similarity NPD6902 Approved
0.6212 Remote Similarity NPD7736 Approved
0.6207 Remote Similarity NPD8029 Clinical (unspecified phase)
0.6202 Remote Similarity NPD6370 Approved
0.6202 Remote Similarity NPD5988 Approved
0.6198 Remote Similarity NPD4730 Approved
0.6198 Remote Similarity NPD4729 Approved
0.6198 Remote Similarity NPD5128 Approved
0.619 Remote Similarity NPD6009 Approved
0.6176 Remote Similarity NPD6926 Approved
0.6176 Remote Similarity NPD6924 Approved
0.6161 Remote Similarity NPD5692 Phase 3
0.6154 Remote Similarity NPD5776 Phase 2
0.6154 Remote Similarity NPD7604 Phase 2
0.6154 Remote Similarity NPD8328 Phase 3
0.6154 Remote Similarity NPD6925 Approved
0.6147 Remote Similarity NPD6893 Approved
0.6147 Remote Similarity NPD7520 Clinical (unspecified phase)
0.614 Remote Similarity NPD6001 Approved
0.614 Remote Similarity NPD5282 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