Structure

Physi-Chem Properties

Molecular Weight:  370.24
Volume:  372.992
LogP:  0.317
LogD:  -0.584
LogS:  -2.486
# Rotatable Bonds:  0
TPSA:  121.38
# H-Bond Aceptor:  6
# H-Bond Donor:  6
# Rings:  4
# Heavy Atoms:  6

MedChem Properties

QED Drug-Likeness Score:  0.361
Synthetic Accessibility Score:  6.302
Fsp3:  1.0
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
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:  -5.098
MDCK Permeability:  0.00035889577702619135
Pgp-inhibitor:  0.002
Pgp-substrate:  0.169
Human Intestinal Absorption (HIA):  0.865
20% Bioavailability (F20%):  0.122
30% Bioavailability (F30%):  0.015

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.778
Plasma Protein Binding (PPB):  22.238344192504883%
Volume Distribution (VD):  1.164
Pgp-substrate:  48.872703552246094%

ADMET: Metabolism

CYP1A2-inhibitor:  0.003
CYP1A2-substrate:  0.114
CYP2C19-inhibitor:  0.003
CYP2C19-substrate:  0.668
CYP2C9-inhibitor:  0.011
CYP2C9-substrate:  0.261
CYP2D6-inhibitor:  0.001
CYP2D6-substrate:  0.145
CYP3A4-inhibitor:  0.037
CYP3A4-substrate:  0.095

ADMET: Excretion

Clearance (CL):  2.33
Half-life (T1/2):  0.13

ADMET: Toxicity

hERG Blockers:  0.045
Human Hepatotoxicity (H-HT):  0.406
Drug-inuced Liver Injury (DILI):  0.025
AMES Toxicity:  0.052
Rat Oral Acute Toxicity:  0.43
Maximum Recommended Daily Dose:  0.583
Skin Sensitization:  0.029
Carcinogencity:  0.023
Eye Corrosion:  0.003
Eye Irritation:  0.009
Respiratory Toxicity:  0.347

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Structure MOL file  
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Similar NPs/Drugs  

  Natural Product: NPC139765

Natural Product ID:  NPC139765
Common Name*:   BWMFRQKICHXLSH-UHFFFAOYSA-N
IUPAC Name:   n.a.
Synonyms:  
Standard InCHIKey:  BWMFRQKICHXLSH-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C20H34O6/c1-16(2)13(21)7-12-18(4,25)11-6-5-10-15(23)19(11,9-17(10,3)24)8-14(22)20(12,16)26/h10-15,21-26H,5-9H2,1-4H3
SMILES:  CC1(C)C(CC2C(C)(C3CCC4C(C3(CC(C12O)O)CC4(C)O)O)O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL1981629
PubChem CID:   3511
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0000259] Prenol lipids
        • [CHEMONTID:0001551] Diterpenoids
          • [CHEMONTID:0002871] Grayanoids
            • [CHEMONTID:0002878] Leucothol and grayanotoxane diterpenoids

*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
NPO25980 Rhododendron molle Species Ericaceae Eukaryota flowers n.a. n.a. PMID[15974620]
NPO25980 Rhododendron molle Species Ericaceae Eukaryota Roots n.a. n.a. PMID[26599832]
NPO25980 Rhododendron molle Species Ericaceae Eukaryota Leaves n.a. n.a. PMID[29272126]
NPO25980 Rhododendron molle Species Ericaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO25980 Rhododendron molle Species Ericaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO25980 Rhododendron molle Species Ericaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO25980 Rhododendron molle Species Ericaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO25980 Rhododendron molle Species Ericaceae 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. 100000.0 nM PMID[572952]
NPT368 Cell Line SN12C Homo sapiens GI50 n.a. 100000.0 nM PMID[572952]
NPT370 Cell Line NCI-H23 Homo sapiens GI50 n.a. 100000.0 nM PMID[572952]
NPT369 Cell Line ACHN Homo sapiens GI50 n.a. 100000.0 nM PMID[572952]
NPT371 Cell Line UO-31 Homo sapiens GI50 n.a. 100000.0 nM PMID[572952]
NPT372 Cell Line HOP-92 Homo sapiens GI50 n.a. 100000.0 nM PMID[572952]
NPT116 Cell Line HL-60 Homo sapiens GI50 n.a. 100000.0 nM PMID[572952]
NPT90 Cell Line DU-145 Homo sapiens GI50 n.a. 100000.0 nM PMID[572952]
NPT374 Cell Line SF-539 Homo sapiens GI50 n.a. 100000.0 nM PMID[572952]
NPT375 Cell Line Malme-3M Homo sapiens GI50 n.a. 100000.0 nM PMID[572952]
NPT373 Cell Line SK-MEL-5 Homo sapiens GI50 n.a. 100000.0 nM PMID[572952]
NPT111 Cell Line K562 Homo sapiens GI50 n.a. 100000.0 nM PMID[572952]
NPT376 Cell Line A498 Homo sapiens GI50 n.a. 100000.0 nM PMID[572952]
NPT112 Cell Line MOLT-4 Homo sapiens GI50 n.a. 100000.0 nM PMID[572952]
NPT378 Cell Line NCI/ADR-RES Homo sapiens GI50 n.a. 100000.0 nM PMID[572952]
NPT380 Cell Line U-251 Homo sapiens GI50 n.a. 100000.0 nM PMID[572952]
NPT381 Cell Line OVCAR-8 Homo sapiens GI50 n.a. 100000.0 nM PMID[572952]
NPT382 Cell Line OVCAR-5 Homo sapiens GI50 n.a. 100000.0 nM PMID[572952]
NPT383 Cell Line SNB-19 Homo sapiens GI50 n.a. 100000.0 nM PMID[572952]
NPT385 Cell Line SR Homo sapiens GI50 n.a. 100000.0 nM PMID[572952]
NPT82 Cell Line MDA-MB-231 Homo sapiens GI50 n.a. 100000.0 nM PMID[572952]
NPT384 Cell Line TK-10 Homo sapiens GI50 n.a. 100000.0 nM PMID[572952]
NPT323 Cell Line SW-620 Homo sapiens GI50 n.a. 100000.0 nM PMID[572952]
NPT386 Cell Line KM12 Homo sapiens GI50 n.a. 100000.0 nM PMID[572952]
NPT455 Cell Line NCI-H522 Homo sapiens GI50 n.a. 100000.0 nM PMID[572952]
NPT387 Cell Line M14 Homo sapiens GI50 n.a. 100000.0 nM PMID[572952]
NPT388 Cell Line NCI-H322M Homo sapiens GI50 n.a. 100000.0 nM PMID[572952]
NPT456 Cell Line OVCAR-4 Homo sapiens GI50 n.a. 100000.0 nM PMID[572952]
NPT457 Cell Line BT-549 Homo sapiens GI50 n.a. 100000.0 nM PMID[572952]
NPT390 Cell Line LOX IMVI Homo sapiens GI50 n.a. 100000.0 nM PMID[572952]
NPT147 Cell Line SK-MEL-2 Homo sapiens GI50 n.a. 100000.0 nM PMID[572952]
NPT81 Cell Line A549 Homo sapiens GI50 n.a. 100000.0 nM PMID[572952]
NPT391 Cell Line HCC 2998 Homo sapiens GI50 n.a. 100000.0 nM PMID[572952]
NPT148 Cell Line HCT-15 Homo sapiens GI50 n.a. 100000.0 nM PMID[572952]
NPT393 Cell Line HCT-116 Homo sapiens GI50 n.a. 100000.0 nM PMID[572952]
NPT395 Cell Line SF-268 Homo sapiens GI50 n.a. 100000.0 nM PMID[572952]
NPT83 Cell Line MCF7 Homo sapiens GI50 n.a. 100000.0 nM PMID[572952]
NPT394 Cell Line EKVX Homo sapiens GI50 n.a. 100000.0 nM PMID[572952]
NPT306 Cell Line PC-3 Homo sapiens GI50 n.a. 100000.0 nM PMID[572952]
NPT396 Cell Line T47D Homo sapiens GI50 n.a. 100000.0 nM PMID[572952]
NPT146 Cell Line SK-OV-3 Homo sapiens GI50 n.a. 100000.0 nM PMID[572952]
NPT398 Cell Line UACC-62 Homo sapiens GI50 n.a. 100000.0 nM PMID[572952]
NPT397 Cell Line NCI-H460 Homo sapiens GI50 n.a. 100000.0 nM PMID[572952]
NPT308 Cell Line CAKI-1 Homo sapiens GI50 n.a. 100000.0 nM PMID[572952]
NPT400 Cell Line MDA-MB-435 Homo sapiens GI50 n.a. 100000.0 nM PMID[572952]
NPT399 Cell Line SF-295 Homo sapiens GI50 n.a. 100000.0 nM PMID[572952]
NPT458 Cell Line IGROV-1 Homo sapiens GI50 n.a. 100000.0 nM PMID[572952]
NPT402 Cell Line Hs-578T Homo sapiens GI50 n.a. 100000.0 nM PMID[572952]
NPT403 Cell Line UACC-257 Homo sapiens GI50 n.a. 100000.0 nM PMID[572952]
NPT401 Cell Line 786-0 Homo sapiens GI50 n.a. 100000.0 nM PMID[572952]
NPT404 Cell Line CCRF-CEM Homo sapiens GI50 n.a. 100000.0 nM PMID[572952]
NPT405 Cell Line NCI-H226 Homo sapiens GI50 n.a. 100000.0 nM PMID[572952]
NPT139 Cell Line HT-29 Homo sapiens GI50 n.a. 100000.0 nM PMID[572952]
NPT170 Cell Line SK-MEL-28 Homo sapiens GI50 n.a. 100000.0 nM PMID[572952]
NPT407 Cell Line COLO 205 Homo sapiens GI50 n.a. 100000.0 nM PMID[572952]

☑ 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 NPC139765 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
1.0 High Similarity NPC131584
0.9324 High Similarity NPC66766
0.9324 High Similarity NPC117137
0.8961 High Similarity NPC29342
0.8961 High Similarity NPC2572
0.8846 High Similarity NPC242016
0.8684 High Similarity NPC269333
0.8649 High Similarity NPC317242
0.8625 High Similarity NPC145245
0.8533 High Similarity NPC163597
0.8421 Intermediate Similarity NPC192046
0.8421 Intermediate Similarity NPC128951
0.8421 Intermediate Similarity NPC185915
0.8421 Intermediate Similarity NPC105208
0.8421 Intermediate Similarity NPC302578
0.8421 Intermediate Similarity NPC477227
0.8415 Intermediate Similarity NPC22376
0.8395 Intermediate Similarity NPC64862
0.8378 Intermediate Similarity NPC470610
0.8378 Intermediate Similarity NPC153719
0.8312 Intermediate Similarity NPC67657
0.8312 Intermediate Similarity NPC18857
0.8267 Intermediate Similarity NPC48795
0.8267 Intermediate Similarity NPC304499
0.8267 Intermediate Similarity NPC475458
0.825 Intermediate Similarity NPC69953
0.8228 Intermediate Similarity NPC473257
0.8205 Intermediate Similarity NPC287452
0.8169 Intermediate Similarity NPC472946
0.8158 Intermediate Similarity NPC158208
0.8158 Intermediate Similarity NPC196136
0.8158 Intermediate Similarity NPC243027
0.8125 Intermediate Similarity NPC475388
0.8108 Intermediate Similarity NPC251201
0.8108 Intermediate Similarity NPC63588
0.8108 Intermediate Similarity NPC232925
0.8082 Intermediate Similarity NPC474756
0.8026 Intermediate Similarity NPC10476
0.8026 Intermediate Similarity NPC228994
0.8026 Intermediate Similarity NPC192501
0.7975 Intermediate Similarity NPC81074
0.7975 Intermediate Similarity NPC477282
0.7973 Intermediate Similarity NPC107919
0.7973 Intermediate Similarity NPC66407
0.7973 Intermediate Similarity NPC477820
0.7949 Intermediate Similarity NPC11907
0.7949 Intermediate Similarity NPC474574
0.7949 Intermediate Similarity NPC64081
0.7949 Intermediate Similarity NPC133596
0.7945 Intermediate Similarity NPC63190
0.7931 Intermediate Similarity NPC39453
0.7857 Intermediate Similarity NPC472396
0.7857 Intermediate Similarity NPC5943
0.7848 Intermediate Similarity NPC147993
0.7805 Intermediate Similarity NPC478054
0.7763 Intermediate Similarity NPC252182
0.7763 Intermediate Similarity NPC187471
0.7763 Intermediate Similarity NPC1340
0.7763 Intermediate Similarity NPC470071
0.7763 Intermediate Similarity NPC127094
0.7738 Intermediate Similarity NPC131365
0.7733 Intermediate Similarity NPC470833
0.7722 Intermediate Similarity NPC476233
0.7714 Intermediate Similarity NPC475968
0.7692 Intermediate Similarity NPC91387
0.7692 Intermediate Similarity NPC231680
0.7692 Intermediate Similarity NPC270306
0.7681 Intermediate Similarity NPC29976
0.7681 Intermediate Similarity NPC150713
0.7681 Intermediate Similarity NPC119425
0.7671 Intermediate Similarity NPC190827
0.7671 Intermediate Similarity NPC243469
0.7671 Intermediate Similarity NPC475943
0.7654 Intermediate Similarity NPC474714
0.7647 Intermediate Similarity NPC210658
0.7647 Intermediate Similarity NPC161928
0.7639 Intermediate Similarity NPC249078
0.7639 Intermediate Similarity NPC236099
0.7639 Intermediate Similarity NPC209686
0.7632 Intermediate Similarity NPC192192
0.7625 Intermediate Similarity NPC471045
0.7619 Intermediate Similarity NPC266651
0.7595 Intermediate Similarity NPC470145
0.759 Intermediate Similarity NPC470070
0.7568 Intermediate Similarity NPC44122
0.7558 Intermediate Similarity NPC128475
0.7532 Intermediate Similarity NPC157777
0.7532 Intermediate Similarity NPC131506
0.7529 Intermediate Similarity NPC471240
0.7529 Intermediate Similarity NPC121981
0.75 Intermediate Similarity NPC320824
0.75 Intermediate Similarity NPC474156
0.75 Intermediate Similarity NPC95804
0.75 Intermediate Similarity NPC470830
0.75 Intermediate Similarity NPC129829
0.75 Intermediate Similarity NPC185547
0.75 Intermediate Similarity NPC299948
0.75 Intermediate Similarity NPC99264
0.75 Intermediate Similarity NPC254037
0.75 Intermediate Similarity NPC241085
0.75 Intermediate Similarity NPC255882
0.747 Intermediate Similarity NPC60018
0.747 Intermediate Similarity NPC470611
0.747 Intermediate Similarity NPC202688
0.747 Intermediate Similarity NPC154043
0.7468 Intermediate Similarity NPC472952
0.7468 Intermediate Similarity NPC472950
0.7439 Intermediate Similarity NPC16449
0.7412 Intermediate Similarity NPC273290
0.7412 Intermediate Similarity NPC232044
0.7403 Intermediate Similarity NPC231945
0.7391 Intermediate Similarity NPC277917
0.7391 Intermediate Similarity NPC89069
0.7391 Intermediate Similarity NPC166894
0.7391 Intermediate Similarity NPC283655
0.7391 Intermediate Similarity NPC178223
0.7381 Intermediate Similarity NPC477285
0.7381 Intermediate Similarity NPC216420
0.7381 Intermediate Similarity NPC85095
0.7381 Intermediate Similarity NPC232023
0.7381 Intermediate Similarity NPC111582
0.7381 Intermediate Similarity NPC211135
0.7375 Intermediate Similarity NPC473916
0.7375 Intermediate Similarity NPC477601
0.7375 Intermediate Similarity NPC477602
0.7368 Intermediate Similarity NPC472741
0.7342 Intermediate Similarity NPC472944
0.7342 Intermediate Similarity NPC472945
0.7333 Intermediate Similarity NPC470424
0.7326 Intermediate Similarity NPC476726
0.7326 Intermediate Similarity NPC476727
0.7326 Intermediate Similarity NPC215968
0.7326 Intermediate Similarity NPC155531
0.7326 Intermediate Similarity NPC472272
0.7317 Intermediate Similarity NPC476176
0.7317 Intermediate Similarity NPC329871
0.7308 Intermediate Similarity NPC100586
0.7308 Intermediate Similarity NPC109457
0.7308 Intermediate Similarity NPC157422
0.7303 Intermediate Similarity NPC473066
0.7297 Intermediate Similarity NPC281540
0.7297 Intermediate Similarity NPC159654
0.7297 Intermediate Similarity NPC199937
0.7297 Intermediate Similarity NPC167995
0.7297 Intermediate Similarity NPC118937
0.7294 Intermediate Similarity NPC227260
0.7284 Intermediate Similarity NPC171658
0.7273 Intermediate Similarity NPC228059
0.7273 Intermediate Similarity NPC20822
0.7273 Intermediate Similarity NPC109744
0.7262 Intermediate Similarity NPC477286
0.7262 Intermediate Similarity NPC296734
0.7262 Intermediate Similarity NPC286719
0.7241 Intermediate Similarity NPC186145
0.7241 Intermediate Similarity NPC474657
0.7237 Intermediate Similarity NPC48079
0.7237 Intermediate Similarity NPC473230
0.7237 Intermediate Similarity NPC475884
0.7229 Intermediate Similarity NPC71535
0.7229 Intermediate Similarity NPC78545
0.7229 Intermediate Similarity NPC470609
0.7222 Intermediate Similarity NPC311246
0.7222 Intermediate Similarity NPC167644
0.7222 Intermediate Similarity NPC256104
0.7222 Intermediate Similarity NPC211845
0.7222 Intermediate Similarity NPC122083
0.7222 Intermediate Similarity NPC182740
0.7215 Intermediate Similarity NPC472341
0.7215 Intermediate Similarity NPC476422
0.7215 Intermediate Similarity NPC473238
0.7209 Intermediate Similarity NPC290612
0.72 Intermediate Similarity NPC165069
0.7195 Intermediate Similarity NPC477817
0.7195 Intermediate Similarity NPC471769
0.7195 Intermediate Similarity NPC477819
0.7191 Intermediate Similarity NPC473956
0.7191 Intermediate Similarity NPC475751
0.7191 Intermediate Similarity NPC279329
0.7191 Intermediate Similarity NPC473542
0.7183 Intermediate Similarity NPC291147
0.7179 Intermediate Similarity NPC282454
0.7162 Intermediate Similarity NPC114891
0.7159 Intermediate Similarity NPC281004
0.7159 Intermediate Similarity NPC475664
0.7143 Intermediate Similarity NPC175
0.7143 Intermediate Similarity NPC45959
0.7143 Intermediate Similarity NPC190940
0.7143 Intermediate Similarity NPC3538
0.7143 Intermediate Similarity NPC477224
0.7143 Intermediate Similarity NPC252253
0.7143 Intermediate Similarity NPC113500
0.7143 Intermediate Similarity NPC469745
0.7143 Intermediate Similarity NPC30687
0.7126 Intermediate Similarity NPC474448
0.7126 Intermediate Similarity NPC477283
0.7126 Intermediate Similarity NPC201273
0.7126 Intermediate Similarity NPC6605
0.7125 Intermediate Similarity NPC477508
0.7125 Intermediate Similarity NPC470151
0.7111 Intermediate Similarity NPC59006

  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 NPC139765 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
0.7973 Intermediate Similarity NPD4267 Clinical (unspecified phase)
0.7179 Intermediate Similarity NPD4787 Phase 1
0.7024 Intermediate Similarity NPD6928 Phase 2
0.6848 Remote Similarity NPD8171 Discontinued
0.6786 Remote Similarity NPD6118 Approved
0.6786 Remote Similarity NPD6114 Approved
0.6786 Remote Similarity NPD6697 Approved
0.6786 Remote Similarity NPD6115 Approved
0.6667 Remote Similarity NPD6116 Phase 1
0.6628 Remote Similarity NPD7525 Registered
0.6623 Remote Similarity NPD371 Approved
0.6548 Remote Similarity NPD6117 Approved
0.6543 Remote Similarity NPD4244 Approved
0.6543 Remote Similarity NPD4245 Approved
0.6463 Remote Similarity NPD4809 Clinical (unspecified phase)
0.6463 Remote Similarity NPD4808 Clinical (unspecified phase)
0.6429 Remote Similarity NPD3703 Phase 2
0.642 Remote Similarity NPD3698 Phase 2
0.6329 Remote Similarity NPD3171 Clinical (unspecified phase)
0.631 Remote Similarity NPD6113 Clinical (unspecified phase)
0.625 Remote Similarity NPD4748 Discontinued
0.6232 Remote Similarity NPD385 Approved
0.6232 Remote Similarity NPD384 Approved
0.622 Remote Similarity NPD3699 Clinical (unspecified phase)
0.622 Remote Similarity NPD3700 Clinical (unspecified phase)
0.62 Remote Similarity NPD1700 Approved
0.6176 Remote Similarity NPD8170 Clinical (unspecified phase)
0.6163 Remote Similarity NPD6933 Approved
0.6154 Remote Similarity NPD7338 Clinical (unspecified phase)
0.6145 Remote Similarity NPD4789 Approved
0.6129 Remote Similarity NPD7524 Approved
0.6118 Remote Similarity NPD1811 Approved
0.6118 Remote Similarity NPD1810 Approved
0.6098 Remote Similarity NPD5360 Phase 3
0.6098 Remote Similarity NPD6705 Phase 1
0.6098 Remote Similarity NPD5361 Clinical (unspecified phase)
0.6067 Remote Similarity NPD6930 Phase 2
0.6067 Remote Similarity NPD6931 Approved
0.6047 Remote Similarity NPD3702 Approved
0.6044 Remote Similarity NPD6695 Phase 3
0.602 Remote Similarity NPD7991 Discontinued
0.5977 Remote Similarity NPD3701 Clinical (unspecified phase)
0.5957 Remote Similarity NPD4751 Clinical (unspecified phase)
0.5955 Remote Similarity NPD6929 Approved
0.5952 Remote Similarity NPD7532 Clinical (unspecified phase)
0.5938 Remote Similarity NPD6701 Clinical (unspecified phase)
0.5938 Remote Similarity NPD6700 Approved
0.593 Remote Similarity NPD6926 Approved
0.593 Remote Similarity NPD6924 Approved
0.5909 Remote Similarity NPD6932 Approved
0.59 Remote Similarity NPD4755 Approved
0.5888 Remote Similarity NPD4634 Approved
0.5882 Remote Similarity NPD4243 Approved
0.5876 Remote Similarity NPD6703 Approved
0.5876 Remote Similarity NPD6702 Approved
0.587 Remote Similarity NPD4788 Approved
0.5862 Remote Similarity NPD6942 Approved
0.5862 Remote Similarity NPD7339 Approved
0.5857 Remote Similarity NPD386 Approved
0.5857 Remote Similarity NPD388 Approved
0.5849 Remote Similarity NPD7320 Approved
0.5816 Remote Similarity NPD4202 Approved
0.5804 Remote Similarity NPD7327 Approved
0.5804 Remote Similarity NPD7328 Approved
0.5789 Remote Similarity NPD8033 Approved
0.5789 Remote Similarity NPD7750 Discontinued
0.5784 Remote Similarity NPD5285 Approved
0.5784 Remote Similarity NPD4700 Approved
0.5784 Remote Similarity NPD5286 Approved
0.5784 Remote Similarity NPD4696 Approved
0.5778 Remote Similarity NPD6683 Phase 2
0.5765 Remote Similarity NPD2687 Approved
0.5765 Remote Similarity NPD2254 Approved
0.5765 Remote Similarity NPD2686 Approved
0.5752 Remote Similarity NPD7516 Approved
0.5747 Remote Similarity NPD4785 Approved
0.5747 Remote Similarity NPD4784 Approved
0.5745 Remote Similarity NPD6893 Approved
0.5745 Remote Similarity NPD7520 Clinical (unspecified phase)
0.573 Remote Similarity NPD5776 Phase 2
0.573 Remote Similarity NPD6925 Approved
0.5714 Remote Similarity NPD7514 Phase 3
0.5714 Remote Similarity NPD586 Phase 1
0.5714 Remote Similarity NPD7509 Discontinued
0.5702 Remote Similarity NPD8377 Approved
0.5702 Remote Similarity NPD8294 Approved
0.5698 Remote Similarity NPD6081 Approved
0.5698 Remote Similarity NPD4758 Discontinued
0.5698 Remote Similarity NPD5777 Approved
0.5696 Remote Similarity NPD3198 Approved
0.5673 Remote Similarity NPD5224 Approved
0.5673 Remote Similarity NPD5225 Approved
0.5673 Remote Similarity NPD4633 Approved
0.5673 Remote Similarity NPD5211 Phase 2
0.5673 Remote Similarity NPD5226 Approved
0.567 Remote Similarity NPD4753 Phase 2
0.5667 Remote Similarity NPD7145 Approved
0.5667 Remote Similarity NPD3671 Phase 1
0.5667 Remote Similarity NPD5364 Discontinued
0.566 Remote Similarity NPD7128 Approved
0.566 Remote Similarity NPD6402 Approved
0.566 Remote Similarity NPD5739 Approved
0.566 Remote Similarity NPD6675 Approved
0.5652 Remote Similarity NPD8378 Approved
0.5652 Remote Similarity NPD8380 Approved
0.5652 Remote Similarity NPD8296 Approved
0.5652 Remote Similarity NPD8379 Approved
0.5652 Remote Similarity NPD8335 Approved
0.5619 Remote Similarity NPD5175 Approved
0.5619 Remote Similarity NPD5174 Approved
0.5607 Remote Similarity NPD6412 Phase 2
0.5604 Remote Similarity NPD7645 Phase 2

  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