Structure

Physi-Chem Properties

Molecular Weight:  338.21
Volume:  356.109
LogP:  3.446
LogD:  3.289
LogS:  -4.031
# Rotatable Bonds:  5
TPSA:  65.13
# H-Bond Aceptor:  5
# H-Bond Donor:  0
# Rings:  2
# Heavy Atoms:  5

MedChem Properties

QED Drug-Likeness Score:  0.448
Synthetic Accessibility Score:  4.747
Fsp3:  0.789
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:  -4.624
MDCK Permeability:  4.9186390242539346e-05
Pgp-inhibitor:  0.986
Pgp-substrate:  0.001
Human Intestinal Absorption (HIA):  0.01
20% Bioavailability (F20%):  0.007
30% Bioavailability (F30%):  0.937

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.569
Plasma Protein Binding (PPB):  72.07744598388672%
Volume Distribution (VD):  1.198
Pgp-substrate:  35.07158660888672%

ADMET: Metabolism

CYP1A2-inhibitor:  0.078
CYP1A2-substrate:  0.056
CYP2C19-inhibitor:  0.017
CYP2C19-substrate:  0.725
CYP2C9-inhibitor:  0.031
CYP2C9-substrate:  0.033
CYP2D6-inhibitor:  0.375
CYP2D6-substrate:  0.09
CYP3A4-inhibitor:  0.317
CYP3A4-substrate:  0.334

ADMET: Excretion

Clearance (CL):  4.47
Half-life (T1/2):  0.689

ADMET: Toxicity

hERG Blockers:  0.026
Human Hepatotoxicity (H-HT):  0.916
Drug-inuced Liver Injury (DILI):  0.806
AMES Toxicity:  0.035
Rat Oral Acute Toxicity:  0.05
Maximum Recommended Daily Dose:  0.019
Skin Sensitization:  0.74
Carcinogencity:  0.107
Eye Corrosion:  0.885
Eye Irritation:  0.216
Respiratory Toxicity:  0.297

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

  Natural Product: NPC93213

Natural Product ID:  NPC93213
Common Name*:   [(1S,2R,3R,4S,6E,10S)-2-Acetyloxy-6,10-Dimethyl-3-Propan-2-Yl-11-Oxabicyclo[8.1.0]Undec-6-En-4-Yl] Acetate
IUPAC Name:   [(1S,2R,3R,4S,6E,10S)-2-acetyloxy-6,10-dimethyl-3-propan-2-yl-11-oxabicyclo[8.1.0]undec-6-en-4-yl] acetate
Synonyms:  
Standard InCHIKey:  DRGFRBPYLMWXJS-RUQCQGRMSA-N
Standard InCHI:  InChI=1S/C19H30O5/c1-11(2)16-15(22-13(4)20)10-12(3)8-7-9-19(6)18(24-19)17(16)23-14(5)21/h8,11,15-18H,7,9-10H2,1-6H3/b12-8+/t15-,16+,17+,18-,19-/m0/s1
SMILES:  CC(C)[C@@H]1[C@H](C/C(=C/CC[C@@]2(C)[C@H]([C@@H]1OC(=O)C)O2)/C)OC(=O)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL1980398
PubChem CID:   13559439
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0000259] Prenol lipids
        • [CHEMONTID:0001550] Sesquiterpenoids
          • [CHEMONTID:0002456] Germacrane 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
NPO28688 Aster tataricus Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[30931559]
NPO28688 Aster tataricus Species Asteraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO1536 Lindera triloba Species Lauraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO1536 Lindera triloba Species Lauraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO28688 Aster tataricus Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO28688 Aster tataricus Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO28688 Aster tataricus Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO1536 Lindera triloba Species Lauraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28688 Aster tataricus Species Asteraceae 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[534830]
NPT367 Cell Line MDA-N Homo sapiens GI50 n.a. 100000.0 nM PMID[534830]
NPT370 Cell Line NCI-H23 Homo sapiens GI50 n.a. 100000.0 nM PMID[534830]
NPT371 Cell Line UO-31 Homo sapiens GI50 n.a. 100000.0 nM PMID[534830]
NPT369 Cell Line ACHN Homo sapiens GI50 n.a. 100000.0 nM PMID[534830]
NPT116 Cell Line HL-60 Homo sapiens GI50 n.a. 100000.0 nM PMID[534830]
NPT372 Cell Line HOP-92 Homo sapiens GI50 n.a. 100000.0 nM PMID[534830]
NPT90 Cell Line DU-145 Homo sapiens GI50 n.a. 100000.0 nM PMID[534830]
NPT373 Cell Line SK-MEL-5 Homo sapiens GI50 n.a. 100000.0 nM PMID[534830]
NPT375 Cell Line Malme-3M Homo sapiens GI50 n.a. 100000.0 nM PMID[534830]
NPT376 Cell Line A498 Homo sapiens GI50 n.a. 100000.0 nM PMID[534830]
NPT111 Cell Line K562 Homo sapiens GI50 n.a. 100000.0 nM PMID[534830]
NPT377 Cell Line OVCAR-3 Homo sapiens GI50 n.a. 100000.0 nM PMID[534830]
NPT112 Cell Line MOLT-4 Homo sapiens GI50 n.a. 100000.0 nM PMID[534830]
NPT379 Cell Line HOP-62 Homo sapiens GI50 n.a. 100000.0 nM PMID[534830]
NPT380 Cell Line U-251 Homo sapiens GI50 n.a. 100000.0 nM PMID[534830]
NPT378 Cell Line NCI/ADR-RES Homo sapiens GI50 n.a. 100000.0 nM PMID[534830]
NPT381 Cell Line OVCAR-8 Homo sapiens GI50 n.a. 100000.0 nM PMID[534830]
NPT382 Cell Line OVCAR-5 Homo sapiens GI50 n.a. 100000.0 nM PMID[534830]
NPT383 Cell Line SNB-19 Homo sapiens GI50 n.a. 100000.0 nM PMID[534830]
NPT82 Cell Line MDA-MB-231 Homo sapiens GI50 n.a. 100000.0 nM PMID[534830]
NPT323 Cell Line SW-620 Homo sapiens GI50 n.a. 100000.0 nM PMID[534830]
NPT384 Cell Line TK-10 Homo sapiens GI50 n.a. 100000.0 nM PMID[534830]
NPT455 Cell Line NCI-H522 Homo sapiens GI50 n.a. 100000.0 nM PMID[534830]
NPT386 Cell Line KM12 Homo sapiens GI50 n.a. 100000.0 nM PMID[534830]
NPT387 Cell Line M14 Homo sapiens GI50 n.a. 100000.0 nM PMID[534830]
NPT388 Cell Line NCI-H322M Homo sapiens GI50 n.a. 100000.0 nM PMID[534830]
NPT389 Cell Line RPMI-8226 Homo sapiens GI50 n.a. 100000.0 nM PMID[534830]
NPT456 Cell Line OVCAR-4 Homo sapiens GI50 n.a. 100000.0 nM PMID[534830]
NPT390 Cell Line LOX IMVI Homo sapiens GI50 n.a. 100000.0 nM PMID[534830]
NPT457 Cell Line BT-549 Homo sapiens GI50 n.a. 100000.0 nM PMID[534830]
NPT147 Cell Line SK-MEL-2 Homo sapiens GI50 n.a. 100000.0 nM PMID[534830]
NPT81 Cell Line A549 Homo sapiens GI50 n.a. 100000.0 nM PMID[534830]
NPT391 Cell Line HCC 2998 Homo sapiens GI50 n.a. 100000.0 nM PMID[534830]
NPT392 Cell Line SNB-75 Homo sapiens GI50 n.a. 100000.0 nM PMID[534830]
NPT148 Cell Line HCT-15 Homo sapiens GI50 n.a. 100000.0 nM PMID[534830]
NPT393 Cell Line HCT-116 Homo sapiens GI50 n.a. 100000.0 nM PMID[534830]
NPT395 Cell Line SF-268 Homo sapiens GI50 n.a. 100000.0 nM PMID[534830]
NPT394 Cell Line EKVX Homo sapiens GI50 n.a. 100000.0 nM PMID[534830]
NPT83 Cell Line MCF7 Homo sapiens GI50 n.a. 100000.0 nM PMID[534830]
NPT306 Cell Line PC-3 Homo sapiens GI50 n.a. 100000.0 nM PMID[534830]
NPT396 Cell Line T47D Homo sapiens GI50 n.a. 100000.0 nM PMID[534830]
NPT146 Cell Line SK-OV-3 Homo sapiens GI50 n.a. 100000.0 nM PMID[534830]
NPT397 Cell Line NCI-H460 Homo sapiens GI50 n.a. 100000.0 nM PMID[534830]
NPT398 Cell Line UACC-62 Homo sapiens GI50 n.a. 100000.0 nM PMID[534830]
NPT400 Cell Line MDA-MB-435 Homo sapiens GI50 n.a. 100000.0 nM PMID[534830]
NPT308 Cell Line CAKI-1 Homo sapiens GI50 n.a. 100000.0 nM PMID[534830]
NPT458 Cell Line IGROV-1 Homo sapiens GI50 n.a. 100000.0 nM PMID[534830]
NPT399 Cell Line SF-295 Homo sapiens GI50 n.a. 100000.0 nM PMID[534830]
NPT402 Cell Line Hs-578T Homo sapiens GI50 n.a. 100000.0 nM PMID[534830]
NPT403 Cell Line UACC-257 Homo sapiens GI50 n.a. 100000.0 nM PMID[534830]
NPT401 Cell Line 786-0 Homo sapiens GI50 n.a. 100000.0 nM PMID[534830]
NPT405 Cell Line NCI-H226 Homo sapiens GI50 n.a. 100000.0 nM PMID[534830]
NPT170 Cell Line SK-MEL-28 Homo sapiens GI50 n.a. 100000.0 nM PMID[534830]
NPT139 Cell Line HT-29 Homo sapiens GI50 n.a. 100000.0 nM PMID[534830]
NPT407 Cell Line COLO 205 Homo sapiens GI50 n.a. 100000.0 nM PMID[534830]
NPT406 Cell Line RXF 393 Homo sapiens GI50 n.a. 100000.0 nM PMID[534830]

☑ 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 NPC93213 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
0.9324 High Similarity NPC474739
0.8718 High Similarity NPC231601
0.8472 Intermediate Similarity NPC329656
0.8289 Intermediate Similarity NPC301525
0.8243 Intermediate Similarity NPC477084
0.8228 Intermediate Similarity NPC207188
0.8095 Intermediate Similarity NPC151770
0.8052 Intermediate Similarity NPC170148
0.7975 Intermediate Similarity NPC86971
0.7973 Intermediate Similarity NPC269841
0.7952 Intermediate Similarity NPC204048
0.7952 Intermediate Similarity NPC50637
0.7949 Intermediate Similarity NPC186109
0.7792 Intermediate Similarity NPC190859
0.7778 Intermediate Similarity NPC474894
0.7738 Intermediate Similarity NPC471480
0.7738 Intermediate Similarity NPC214315
0.7727 Intermediate Similarity NPC473330
0.7727 Intermediate Similarity NPC473316
0.7722 Intermediate Similarity NPC84360
0.7674 Intermediate Similarity NPC166919
0.7674 Intermediate Similarity NPC475971
0.7662 Intermediate Similarity NPC476709
0.7647 Intermediate Similarity NPC231889
0.7625 Intermediate Similarity NPC3852
0.7619 Intermediate Similarity NPC38468
0.7619 Intermediate Similarity NPC50362
0.7619 Intermediate Similarity NPC319795
0.759 Intermediate Similarity NPC475622
0.759 Intermediate Similarity NPC108045
0.7586 Intermediate Similarity NPC475748
0.7558 Intermediate Similarity NPC233997
0.7558 Intermediate Similarity NPC309656
0.7556 Intermediate Similarity NPC279621
0.7531 Intermediate Similarity NPC471537
0.7531 Intermediate Similarity NPC325869
0.7529 Intermediate Similarity NPC137253
0.7528 Intermediate Similarity NPC471147
0.75 Intermediate Similarity NPC476703
0.75 Intermediate Similarity NPC78673
0.75 Intermediate Similarity NPC160517
0.75 Intermediate Similarity NPC186155
0.75 Intermediate Similarity NPC158061
0.7473 Intermediate Similarity NPC471140
0.7468 Intermediate Similarity NPC475861
0.7444 Intermediate Similarity NPC475659
0.7416 Intermediate Similarity NPC228451
0.7416 Intermediate Similarity NPC125674
0.7416 Intermediate Similarity NPC212486
0.7416 Intermediate Similarity NPC475838
0.7412 Intermediate Similarity NPC474547
0.7407 Intermediate Similarity NPC264610
0.7407 Intermediate Similarity NPC474005
0.7407 Intermediate Similarity NPC23187
0.7407 Intermediate Similarity NPC477089
0.7403 Intermediate Similarity NPC475310
0.7391 Intermediate Similarity NPC208233
0.7391 Intermediate Similarity NPC279561
0.7386 Intermediate Similarity NPC312042
0.7386 Intermediate Similarity NPC251385
0.7386 Intermediate Similarity NPC49342
0.7386 Intermediate Similarity NPC3952
0.7381 Intermediate Similarity NPC272814
0.7381 Intermediate Similarity NPC475842
0.7381 Intermediate Similarity NPC170286
0.7363 Intermediate Similarity NPC473859
0.7349 Intermediate Similarity NPC118116
0.7349 Intermediate Similarity NPC141810
0.7333 Intermediate Similarity NPC57405
0.7333 Intermediate Similarity NPC474247
0.7333 Intermediate Similarity NPC161998
0.7333 Intermediate Similarity NPC140543
0.7333 Intermediate Similarity NPC476267
0.7333 Intermediate Similarity NPC303942
0.7326 Intermediate Similarity NPC61527
0.7317 Intermediate Similarity NPC617
0.7312 Intermediate Similarity NPC288876
0.7284 Intermediate Similarity NPC40049
0.7273 Intermediate Similarity NPC74722
0.7273 Intermediate Similarity NPC304690
0.7263 Intermediate Similarity NPC19239
0.7263 Intermediate Similarity NPC474166
0.7253 Intermediate Similarity NPC471141
0.7253 Intermediate Similarity NPC270013
0.7253 Intermediate Similarity NPC14961
0.7253 Intermediate Similarity NPC220221
0.725 Intermediate Similarity NPC113639
0.7241 Intermediate Similarity NPC5130
0.7241 Intermediate Similarity NPC474765
0.7241 Intermediate Similarity NPC476600
0.7237 Intermediate Similarity NPC473357
0.7237 Intermediate Similarity NPC193029
0.7234 Intermediate Similarity NPC164598
0.7234 Intermediate Similarity NPC474339
0.7234 Intermediate Similarity NPC264477
0.7234 Intermediate Similarity NPC477511
0.7229 Intermediate Similarity NPC475946
0.7215 Intermediate Similarity NPC477085
0.7204 Intermediate Similarity NPC473326
0.7204 Intermediate Similarity NPC152480
0.7176 Intermediate Similarity NPC474703
0.7176 Intermediate Similarity NPC127917
0.7176 Intermediate Similarity NPC239308
0.7176 Intermediate Similarity NPC475989
0.7174 Intermediate Similarity NPC17585
0.7174 Intermediate Similarity NPC35498
0.7174 Intermediate Similarity NPC230800
0.7174 Intermediate Similarity NPC476315
0.7174 Intermediate Similarity NPC57664
0.7159 Intermediate Similarity NPC281516
0.7158 Intermediate Similarity NPC471148
0.7143 Intermediate Similarity NPC305698
0.7143 Intermediate Similarity NPC81386
0.7143 Intermediate Similarity NPC476716
0.7143 Intermediate Similarity NPC223604
0.7143 Intermediate Similarity NPC79277
0.7143 Intermediate Similarity NPC474035
0.7143 Intermediate Similarity NPC77003
0.7143 Intermediate Similarity NPC475481
0.7126 Intermediate Similarity NPC261253
0.7126 Intermediate Similarity NPC474045
0.7126 Intermediate Similarity NPC311163
0.7113 Intermediate Similarity NPC9303
0.7113 Intermediate Similarity NPC475802
0.7113 Intermediate Similarity NPC16313
0.7111 Intermediate Similarity NPC208839
0.7111 Intermediate Similarity NPC184463
0.7108 Intermediate Similarity NPC476701
0.7089 Intermediate Similarity NPC477087
0.7089 Intermediate Similarity NPC477086
0.7089 Intermediate Similarity NPC472254
0.7079 Intermediate Similarity NPC161560
0.7079 Intermediate Similarity NPC4986
0.7079 Intermediate Similarity NPC133450
0.7079 Intermediate Similarity NPC307411
0.7065 Intermediate Similarity NPC107476
0.7065 Intermediate Similarity NPC291709
0.7065 Intermediate Similarity NPC241407
0.7065 Intermediate Similarity NPC240838
0.7059 Intermediate Similarity NPC103171
0.7059 Intermediate Similarity NPC475936
0.7053 Intermediate Similarity NPC473332
0.7051 Intermediate Similarity NPC101622
0.7051 Intermediate Similarity NPC22301
0.7045 Intermediate Similarity NPC475087
0.7045 Intermediate Similarity NPC266957
0.7045 Intermediate Similarity NPC475703
0.7041 Intermediate Similarity NPC475510
0.7041 Intermediate Similarity NPC474421
0.7041 Intermediate Similarity NPC326994
0.7041 Intermediate Similarity NPC194620
0.7041 Intermediate Similarity NPC324327
0.7041 Intermediate Similarity NPC475587
0.7041 Intermediate Similarity NPC72813
0.7033 Intermediate Similarity NPC476300
0.7033 Intermediate Similarity NPC477615
0.7033 Intermediate Similarity NPC475912
0.7024 Intermediate Similarity NPC469802
0.7024 Intermediate Similarity NPC103634
0.7024 Intermediate Similarity NPC233332
0.7021 Intermediate Similarity NPC222303
0.7013 Intermediate Similarity NPC259299
0.7013 Intermediate Similarity NPC163290
0.7011 Intermediate Similarity NPC471379
0.7011 Intermediate Similarity NPC476725
0.7011 Intermediate Similarity NPC196911
0.7011 Intermediate Similarity NPC477746
0.7011 Intermediate Similarity NPC471494
0.7011 Intermediate Similarity NPC477747
0.701 Intermediate Similarity NPC477510
0.701 Intermediate Similarity NPC471143
0.7 Intermediate Similarity NPC179394
0.7 Intermediate Similarity NPC475855
0.7 Intermediate Similarity NPC329857
0.7 Intermediate Similarity NPC62815
0.7 Intermediate Similarity NPC177668
0.7 Intermediate Similarity NPC469718
0.7 Intermediate Similarity NPC144133
0.7 Intermediate Similarity NPC51004
0.6988 Remote Similarity NPC474341
0.6979 Remote Similarity NPC283567
0.6979 Remote Similarity NPC470972
0.6979 Remote Similarity NPC183571
0.6977 Remote Similarity NPC49208
0.6977 Remote Similarity NPC5958
0.6977 Remote Similarity NPC474193
0.6977 Remote Similarity NPC170377
0.6977 Remote Similarity NPC12283
0.6977 Remote Similarity NPC474472
0.6977 Remote Similarity NPC257358
0.6977 Remote Similarity NPC53867
0.6974 Remote Similarity NPC61503
0.697 Remote Similarity NPC327286
0.697 Remote Similarity NPC233379
0.697 Remote Similarity NPC473939
0.697 Remote Similarity NPC55972
0.697 Remote Similarity NPC70235
0.697 Remote Similarity NPC474664
0.697 Remote Similarity NPC94377
0.697 Remote Similarity NPC14862

  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 NPC93213 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
0.7619 Intermediate Similarity NPD1733 Clinical (unspecified phase)
0.7386 Intermediate Similarity NPD7838 Discovery
0.72 Intermediate Similarity NPD2685 Clinical (unspecified phase)
0.7191 Intermediate Similarity NPD6698 Approved
0.7191 Intermediate Similarity NPD46 Approved
0.7128 Intermediate Similarity NPD6648 Approved
0.7079 Intermediate Similarity NPD1695 Approved
0.7053 Intermediate Similarity NPD5344 Discontinued
0.7 Intermediate Similarity NPD3168 Discontinued
0.6739 Remote Similarity NPD7983 Approved
0.6633 Remote Similarity NPD3653 Clinical (unspecified phase)
0.6556 Remote Similarity NPD4249 Approved
0.6484 Remote Similarity NPD4250 Approved
0.6484 Remote Similarity NPD4251 Approved
0.6437 Remote Similarity NPD5790 Clinical (unspecified phase)
0.6437 Remote Similarity NPD4819 Approved
0.6437 Remote Similarity NPD4821 Approved
0.6437 Remote Similarity NPD4822 Approved
0.6437 Remote Similarity NPD4820 Approved
0.6373 Remote Similarity NPD7899 Clinical (unspecified phase)
0.6346 Remote Similarity NPD6371 Approved
0.6333 Remote Similarity NPD7338 Clinical (unspecified phase)
0.6327 Remote Similarity NPD8029 Clinical (unspecified phase)
0.6316 Remote Similarity NPD5778 Approved
0.6316 Remote Similarity NPD5779 Approved
0.6304 Remote Similarity NPD7524 Approved
0.6292 Remote Similarity NPD6435 Approved
0.6275 Remote Similarity NPD6008 Approved
0.625 Remote Similarity NPD5282 Discontinued
0.6222 Remote Similarity NPD6695 Phase 3
0.6222 Remote Similarity NPD7154 Phase 3
0.6207 Remote Similarity NPD4268 Approved
0.6207 Remote Similarity NPD4271 Approved
0.618 Remote Similarity NPD5369 Approved
0.617 Remote Similarity NPD5764 Clinical (unspecified phase)
0.617 Remote Similarity NPD6101 Approved
0.6117 Remote Similarity NPD5357 Phase 1
0.6087 Remote Similarity NPD6082 Clinical (unspecified phase)
0.6067 Remote Similarity NPD5368 Approved
0.6058 Remote Similarity NPD5954 Clinical (unspecified phase)
0.6044 Remote Similarity NPD5362 Discontinued
0.6042 Remote Similarity NPD6411 Approved
0.6042 Remote Similarity NPD7637 Suspended
0.6026 Remote Similarity NPD1145 Discontinued
0.6 Remote Similarity NPD6051 Approved
0.6 Remote Similarity NPD6686 Approved
0.6 Remote Similarity NPD4225 Approved
0.5981 Remote Similarity NPD8413 Clinical (unspecified phase)
0.5979 Remote Similarity NPD6399 Phase 3
0.5957 Remote Similarity NPD7750 Discontinued
0.5943 Remote Similarity NPD4061 Clinical (unspecified phase)
0.5934 Remote Similarity NPD4752 Clinical (unspecified phase)
0.5934 Remote Similarity NPD5209 Approved
0.5889 Remote Similarity NPD6931 Approved
0.5889 Remote Similarity NPD6930 Phase 2
0.5888 Remote Similarity NPD5955 Clinical (unspecified phase)
0.587 Remote Similarity NPD5331 Approved
0.587 Remote Similarity NPD5332 Approved
0.5859 Remote Similarity NPD1698 Clinical (unspecified phase)
0.5851 Remote Similarity NPD5330 Approved
0.5851 Remote Similarity NPD7146 Approved
0.5851 Remote Similarity NPD7521 Approved
0.5851 Remote Similarity NPD6409 Approved
0.5851 Remote Similarity NPD6684 Approved
0.5851 Remote Similarity NPD7334 Approved
0.5842 Remote Similarity NPD7638 Approved
0.5824 Remote Similarity NPD4790 Discontinued
0.58 Remote Similarity NPD7839 Suspended
0.5795 Remote Similarity NPD6933 Approved
0.5784 Remote Similarity NPD7640 Approved
0.5784 Remote Similarity NPD7639 Approved
0.578 Remote Similarity NPD6053 Discontinued
0.5778 Remote Similarity NPD6929 Approved
0.5761 Remote Similarity NPD4270 Approved
0.5761 Remote Similarity NPD4269 Approved
0.5758 Remote Similarity NPD7901 Clinical (unspecified phase)
0.5758 Remote Similarity NPD7900 Approved
0.5755 Remote Similarity NPD6412 Phase 2
0.575 Remote Similarity NPD368 Approved
0.5747 Remote Similarity NPD6924 Approved
0.5747 Remote Similarity NPD6926 Approved
0.573 Remote Similarity NPD6932 Approved
0.5729 Remote Similarity NPD5737 Approved
0.5729 Remote Similarity NPD7513 Clinical (unspecified phase)
0.5729 Remote Similarity NPD6903 Approved
0.5729 Remote Similarity NPD6672 Approved
0.5714 Remote Similarity NPD7087 Discontinued
0.57 Remote Similarity NPD5695 Phase 3
0.5684 Remote Similarity NPD6422 Discontinued
0.5684 Remote Similarity NPD5786 Approved
0.5682 Remote Similarity NPD8039 Approved
0.5667 Remote Similarity NPD5784 Clinical (unspecified phase)
0.5664 Remote Similarity NPD7327 Approved
0.5664 Remote Similarity NPD7328 Approved
0.5652 Remote Similarity NPD8033 Approved
0.5638 Remote Similarity NPD6400 Clinical (unspecified phase)
0.5614 Remote Similarity NPD7516 Approved
0.561 Remote Similarity NPD5325 Clinical (unspecified phase)
0.5607 Remote Similarity NPD6685 Approved
0.5604 Remote Similarity NPD6683 Phase 2
0.56 Remote Similarity NPD7748 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