Structure

Physi-Chem Properties

Molecular Weight:  470.34
Volume:  523.745
LogP:  6.573
LogD:  4.202
LogS:  -4.69
# Rotatable Bonds:  9
TPSA:  74.6
# H-Bond Aceptor:  4
# H-Bond Donor:  2
# Rings:  3
# Heavy Atoms:  4

MedChem Properties

QED Drug-Likeness Score:  0.342
Synthetic Accessibility Score:  5.01
Fsp3:  0.733
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Rejected
GSK Rule:  Rejected
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -5.648
MDCK Permeability:  9.87468047242146e-06
Pgp-inhibitor:  0.001
Pgp-substrate:  0.001
Human Intestinal Absorption (HIA):  0.01
20% Bioavailability (F20%):  0.014
30% Bioavailability (F30%):  0.004

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.277
Plasma Protein Binding (PPB):  99.17060852050781%
Volume Distribution (VD):  0.495
Pgp-substrate:  3.496603012084961%

ADMET: Metabolism

CYP1A2-inhibitor:  0.013
CYP1A2-substrate:  0.315
CYP2C19-inhibitor:  0.01
CYP2C19-substrate:  0.677
CYP2C9-inhibitor:  0.055
CYP2C9-substrate:  0.935
CYP2D6-inhibitor:  0.003
CYP2D6-substrate:  0.154
CYP3A4-inhibitor:  0.11
CYP3A4-substrate:  0.122

ADMET: Excretion

Clearance (CL):  3.142
Half-life (T1/2):  0.231

ADMET: Toxicity

hERG Blockers:  0.01
Human Hepatotoxicity (H-HT):  0.324
Drug-inuced Liver Injury (DILI):  0.02
AMES Toxicity:  0.002
Rat Oral Acute Toxicity:  0.509
Maximum Recommended Daily Dose:  0.336
Skin Sensitization:  0.169
Carcinogencity:  0.528
Eye Corrosion:  0.372
Eye Irritation:  0.017
Respiratory Toxicity:  0.964

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

  Natural Product: NPC164577

Natural Product ID:  NPC164577
Common Name*:   (Z,6R)-6-[(3Ar,6S,7S,9As,9Bs)-6-(2-Carboxyethyl)-3A,6,9B-Trimethyl-7-Prop-1-En-2-Yl-1,2,3,4,7,8,9,9A-Octahydrocyclopenta[A]Naphthalen-3-Yl]-2-Methylhept-2-Enoic Acid
IUPAC Name:   (Z,6R)-6-[(3aR,6S,7S,9aS,9bS)-6-(2-carboxyethyl)-3a,6,9b-trimethyl-7-prop-1-en-2-yl-1,2,3,4,7,8,9,9a-octahydrocyclopenta[a]naphthalen-3-yl]-2-methylhept-2-enoic acid
Synonyms:  
Standard InCHIKey:  JGNPDWQZTUZFHK-LYNKRMMFSA-N
Standard InCHI:  InChI=1S/C30H46O4/c1-19(2)22-11-12-25-24(28(22,5)16-15-26(31)32)14-18-29(6)23(13-17-30(25,29)7)20(3)9-8-10-21(4)27(33)34/h10,14,20,22-23,25H,1,8-9,11-13,15-18H2,2-7H3,(H,31,32)(H,33,34)/b21-10-/t20-,22+,23?,25-,28+,29-,30+/m1/s1
SMILES:  C=C(C)[C@@H]1CC[C@@H]2C(=CC[C@]3(C)C(CC[C@@]23C)[C@H](C)CC/C=C(/C)C(=O)O)[C@@]1(C)CCC(=O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL1976802
PubChem CID:   5384417
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0000259] Prenol lipids
        • [CHEMONTID:0001553] Triterpenoids

*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
NPO8367 Fructus schiandrae n.a. n.a. n.a. n.a. n.a. n.a. Database[HerDing]
NPO8367 Fructus schiandrae n.a. n.a. n.a. n.a. n.a. n.a. Database[TCMID]

☑ 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. 33419.5 nM PMID[487587]
NPT367 Cell Line MDA-N Homo sapiens GI50 n.a. 28313.92 nM PMID[487587]
NPT369 Cell Line ACHN Homo sapiens GI50 n.a. 18967.06 nM PMID[487587]
NPT370 Cell Line NCI-H23 Homo sapiens GI50 n.a. 23988.33 nM PMID[487587]
NPT371 Cell Line UO-31 Homo sapiens GI50 n.a. 16672.47 nM PMID[487587]
NPT372 Cell Line HOP-92 Homo sapiens GI50 n.a. 19186.69 nM PMID[487587]
NPT116 Cell Line HL-60 Homo sapiens GI50 n.a. 26791.68 nM PMID[487587]
NPT374 Cell Line SF-539 Homo sapiens GI50 n.a. 30408.85 nM PMID[487587]
NPT90 Cell Line DU-145 Homo sapiens GI50 n.a. 24210.29 nM PMID[487587]
NPT373 Cell Line SK-MEL-5 Homo sapiens GI50 n.a. 16943.38 nM PMID[487587]
NPT375 Cell Line Malme-3M Homo sapiens GI50 n.a. 25468.3 nM PMID[487587]
NPT376 Cell Line A498 Homo sapiens GI50 n.a. 33342.64 nM PMID[487587]
NPT111 Cell Line K562 Homo sapiens GI50 n.a. 32960.97 nM PMID[487587]
NPT377 Cell Line OVCAR-3 Homo sapiens GI50 n.a. 19906.73 nM PMID[487587]
NPT379 Cell Line HOP-62 Homo sapiens GI50 n.a. 52844.53 nM PMID[487587]
NPT380 Cell Line U-251 Homo sapiens GI50 n.a. 24490.63 nM PMID[487587]
NPT381 Cell Line OVCAR-8 Homo sapiens GI50 n.a. 34434.99 nM PMID[487587]
NPT382 Cell Line OVCAR-5 Homo sapiens GI50 n.a. 30478.95 nM PMID[487587]
NPT383 Cell Line SNB-19 Homo sapiens GI50 n.a. 34040.82 nM PMID[487587]
NPT82 Cell Line MDA-MB-231 Homo sapiens GI50 n.a. 25176.77 nM PMID[487587]
NPT384 Cell Line TK-10 Homo sapiens GI50 n.a. 36559.48 nM PMID[487587]
NPT385 Cell Line SR Homo sapiens GI50 n.a. 21281.39 nM PMID[487587]
NPT323 Cell Line SW-620 Homo sapiens GI50 n.a. 28973.44 nM PMID[487587]
NPT455 Cell Line NCI-H522 Homo sapiens GI50 n.a. 22698.65 nM PMID[487587]
NPT386 Cell Line KM12 Homo sapiens GI50 n.a. 23442.29 nM PMID[487587]
NPT387 Cell Line M14 Homo sapiens GI50 n.a. 29512.09 nM PMID[487587]
NPT388 Cell Line NCI-H322M Homo sapiens GI50 n.a. 26424.09 nM PMID[487587]
NPT389 Cell Line RPMI-8226 Homo sapiens GI50 n.a. 22855.99 nM PMID[487587]
NPT456 Cell Line OVCAR-4 Homo sapiens GI50 n.a. 36643.76 nM PMID[487587]
NPT390 Cell Line LOX IMVI Homo sapiens GI50 n.a. 19186.69 nM PMID[487587]
NPT457 Cell Line BT-549 Homo sapiens GI50 n.a. 21627.19 nM PMID[487587]
NPT147 Cell Line SK-MEL-2 Homo sapiens GI50 n.a. 20183.66 nM PMID[487587]
NPT81 Cell Line A549 Homo sapiens GI50 n.a. 36812.9 nM PMID[487587]
NPT392 Cell Line SNB-75 Homo sapiens GI50 n.a. 34355.79 nM PMID[487587]
NPT391 Cell Line HCC 2998 Homo sapiens GI50 n.a. 18793.17 nM PMID[487587]
NPT393 Cell Line HCT-116 Homo sapiens GI50 n.a. 22335.72 nM PMID[487587]
NPT148 Cell Line HCT-15 Homo sapiens GI50 n.a. 21330.45 nM PMID[487587]
NPT395 Cell Line SF-268 Homo sapiens GI50 n.a. 37670.38 nM PMID[487587]
NPT394 Cell Line EKVX Homo sapiens GI50 n.a. 36307.81 nM PMID[487587]
NPT83 Cell Line MCF7 Homo sapiens GI50 n.a. 39627.8 nM PMID[487587]
NPT306 Cell Line PC-3 Homo sapiens GI50 n.a. 24888.57 nM PMID[487587]
NPT396 Cell Line T47D Homo sapiens GI50 n.a. 45814.19 nM PMID[487587]
NPT146 Cell Line SK-OV-3 Homo sapiens GI50 n.a. 37670.38 nM PMID[487587]
NPT397 Cell Line NCI-H460 Homo sapiens GI50 n.a. 20417.38 nM PMID[487587]
NPT398 Cell Line UACC-62 Homo sapiens GI50 n.a. 20370.42 nM PMID[487587]
NPT400 Cell Line MDA-MB-435 Homo sapiens GI50 n.a. 29174.27 nM PMID[487587]
NPT308 Cell Line CAKI-1 Homo sapiens GI50 n.a. 23768.4 nM PMID[487587]
NPT458 Cell Line IGROV-1 Homo sapiens GI50 n.a. 28183.83 nM PMID[487587]
NPT399 Cell Line SF-295 Homo sapiens GI50 n.a. 30269.13 nM PMID[487587]
NPT402 Cell Line Hs-578T Homo sapiens GI50 n.a. 33342.64 nM PMID[487587]
NPT403 Cell Line UACC-257 Homo sapiens GI50 n.a. 23768.4 nM PMID[487587]
NPT401 Cell Line 786-0 Homo sapiens GI50 n.a. 21827.3 nM PMID[487587]
NPT404 Cell Line CCRF-CEM Homo sapiens GI50 n.a. 21877.62 nM PMID[487587]
NPT405 Cell Line NCI-H226 Homo sapiens GI50 n.a. 21281.39 nM PMID[487587]
NPT139 Cell Line HT-29 Homo sapiens GI50 n.a. 21677.04 nM PMID[487587]
NPT170 Cell Line SK-MEL-28 Homo sapiens GI50 n.a. 27925.44 nM PMID[487587]
NPT407 Cell Line COLO 205 Homo sapiens GI50 n.a. 22594.36 nM PMID[487587]
NPT406 Cell Line RXF 393 Homo sapiens GI50 n.a. 19408.86 nM PMID[487587]

☑ 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 NPC164577 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
0.9872 High Similarity NPC97913
0.9747 High Similarity NPC472865
0.9506 High Similarity NPC186975
0.95 High Similarity NPC472864
0.95 High Similarity NPC19849
0.939 High Similarity NPC236618
0.9277 High Similarity NPC117122
0.9268 High Similarity NPC472869
0.9167 High Similarity NPC262043
0.9167 High Similarity NPC66344
0.9157 High Similarity NPC136948
0.9125 High Similarity NPC477372
0.9048 High Similarity NPC472870
0.9024 High Similarity NPC248758
0.8987 High Similarity NPC198240
0.8953 High Similarity NPC470113
0.8953 High Similarity NPC204341
0.8916 High Similarity NPC269638
0.8916 High Similarity NPC29447
0.8875 High Similarity NPC477371
0.8861 High Similarity NPC61952
0.8846 High Similarity NPC476795
0.8837 High Similarity NPC472866
0.8795 High Similarity NPC165064
0.878 High Similarity NPC472239
0.878 High Similarity NPC3511
0.878 High Similarity NPC133391
0.878 High Similarity NPC142253
0.878 High Similarity NPC320514
0.8764 High Similarity NPC456
0.8764 High Similarity NPC472941
0.8736 High Similarity NPC473986
0.8736 High Similarity NPC476187
0.8736 High Similarity NPC474018
0.8721 High Similarity NPC214387
0.8706 High Similarity NPC128644
0.869 High Similarity NPC8571
0.8675 High Similarity NPC310470
0.8675 High Similarity NPC470015
0.8675 High Similarity NPC49019
0.8675 High Similarity NPC168188
0.8675 High Similarity NPC477373
0.8659 High Similarity NPC147066
0.8659 High Similarity NPC278459
0.8659 High Similarity NPC201912
0.8659 High Similarity NPC38350
0.8652 High Similarity NPC293052
0.8652 High Similarity NPC476174
0.8642 High Similarity NPC158846
0.8642 High Similarity NPC196827
0.8642 High Similarity NPC274996
0.8636 High Similarity NPC472871
0.8625 High Similarity NPC97377
0.8621 High Similarity NPC477147
0.8621 High Similarity NPC477149
0.859 High Similarity NPC35656
0.8571 High Similarity NPC166745
0.8571 High Similarity NPC87552
0.8571 High Similarity NPC194937
0.8571 High Similarity NPC476038
0.8571 High Similarity NPC235464
0.8571 High Similarity NPC197386
0.8556 High Similarity NPC29152
0.8554 High Similarity NPC472867
0.8554 High Similarity NPC260956
0.8519 High Similarity NPC74410
0.8519 High Similarity NPC179028
0.8506 High Similarity NPC310236
0.85 High Similarity NPC180886
0.8488 Intermediate Similarity NPC476409
0.8478 Intermediate Similarity NPC287833
0.8478 Intermediate Similarity NPC476274
0.8471 Intermediate Similarity NPC60350
0.8471 Intermediate Similarity NPC123319
0.8471 Intermediate Similarity NPC142649
0.8471 Intermediate Similarity NPC94531
0.8471 Intermediate Similarity NPC311702
0.8471 Intermediate Similarity NPC283733
0.8462 Intermediate Similarity NPC160817
0.8462 Intermediate Similarity NPC156546
0.8462 Intermediate Similarity NPC476253
0.8452 Intermediate Similarity NPC279639
0.8452 Intermediate Similarity NPC167103
0.8452 Intermediate Similarity NPC83569
0.8452 Intermediate Similarity NPC69279
0.8452 Intermediate Similarity NPC3856
0.8444 Intermediate Similarity NPC469995
0.8444 Intermediate Similarity NPC174948
0.8444 Intermediate Similarity NPC171395
0.8444 Intermediate Similarity NPC318282
0.8444 Intermediate Similarity NPC173875
0.8434 Intermediate Similarity NPC40228
0.8391 Intermediate Similarity NPC193843
0.8391 Intermediate Similarity NPC48107
0.8391 Intermediate Similarity NPC249889
0.8391 Intermediate Similarity NPC72397
0.8387 Intermediate Similarity NPC476240
0.8387 Intermediate Similarity NPC476223
0.8387 Intermediate Similarity NPC472924
0.8387 Intermediate Similarity NPC224720
0.8387 Intermediate Similarity NPC99411
0.8375 Intermediate Similarity NPC472327
0.8353 Intermediate Similarity NPC16287
0.8353 Intermediate Similarity NPC178025
0.8353 Intermediate Similarity NPC181743
0.8352 Intermediate Similarity NPC328371
0.8352 Intermediate Similarity NPC250757
0.8352 Intermediate Similarity NPC301534
0.8333 Intermediate Similarity NPC469805
0.8333 Intermediate Similarity NPC469804
0.8333 Intermediate Similarity NPC296367
0.8333 Intermediate Similarity NPC469406
0.8333 Intermediate Similarity NPC469806
0.8333 Intermediate Similarity NPC469799
0.8315 Intermediate Similarity NPC165904
0.8315 Intermediate Similarity NPC179517
0.8315 Intermediate Similarity NPC473998
0.8298 Intermediate Similarity NPC293753
0.8295 Intermediate Similarity NPC262858
0.8295 Intermediate Similarity NPC146554
0.8295 Intermediate Similarity NPC5509
0.8295 Intermediate Similarity NPC174342
0.8295 Intermediate Similarity NPC123912
0.8295 Intermediate Similarity NPC473999
0.8295 Intermediate Similarity NPC309603
0.8295 Intermediate Similarity NPC472240
0.8293 Intermediate Similarity NPC321514
0.8293 Intermediate Similarity NPC260385
0.8293 Intermediate Similarity NPC280654
0.8293 Intermediate Similarity NPC239098
0.8293 Intermediate Similarity NPC110094
0.8293 Intermediate Similarity NPC169095
0.8293 Intermediate Similarity NPC275494
0.8293 Intermediate Similarity NPC471409
0.828 Intermediate Similarity NPC241221
0.828 Intermediate Similarity NPC51370
0.8276 Intermediate Similarity NPC167877
0.8276 Intermediate Similarity NPC96496
0.8272 Intermediate Similarity NPC246445
0.8261 Intermediate Similarity NPC320306
0.8261 Intermediate Similarity NPC253826
0.8256 Intermediate Similarity NPC11711
0.8256 Intermediate Similarity NPC473038
0.8256 Intermediate Similarity NPC474083
0.8256 Intermediate Similarity NPC471224
0.8256 Intermediate Similarity NPC65661
0.8235 Intermediate Similarity NPC472740
0.8235 Intermediate Similarity NPC215893
0.8222 Intermediate Similarity NPC151722
0.8222 Intermediate Similarity NPC474736
0.8222 Intermediate Similarity NPC472930
0.8222 Intermediate Similarity NPC38232
0.8222 Intermediate Similarity NPC214697
0.8214 Intermediate Similarity NPC471898
0.8202 Intermediate Similarity NPC48010
0.8202 Intermediate Similarity NPC469400
0.8193 Intermediate Similarity NPC199595
0.8193 Intermediate Similarity NPC327674
0.8182 Intermediate Similarity NPC104560
0.8172 Intermediate Similarity NPC98868
0.8172 Intermediate Similarity NPC471717
0.8171 Intermediate Similarity NPC471899
0.8171 Intermediate Similarity NPC107039
0.8171 Intermediate Similarity NPC471897
0.8171 Intermediate Similarity NPC165711
0.8161 Intermediate Similarity NPC155011
0.8148 Intermediate Similarity NPC192540
0.8148 Intermediate Similarity NPC476346
0.8148 Intermediate Similarity NPC469803
0.8148 Intermediate Similarity NPC279666
0.814 Intermediate Similarity NPC209882
0.814 Intermediate Similarity NPC96095
0.814 Intermediate Similarity NPC473246
0.814 Intermediate Similarity NPC214043
0.814 Intermediate Similarity NPC85774
0.8132 Intermediate Similarity NPC184870
0.8132 Intermediate Similarity NPC8993
0.8125 Intermediate Similarity NPC109576
0.8125 Intermediate Similarity NPC180015
0.8125 Intermediate Similarity NPC130016
0.8125 Intermediate Similarity NPC56747
0.8118 Intermediate Similarity NPC327969
0.8118 Intermediate Similarity NPC240302
0.8118 Intermediate Similarity NPC100297
0.8118 Intermediate Similarity NPC321289
0.8118 Intermediate Similarity NPC193347
0.8111 Intermediate Similarity NPC475806
0.8111 Intermediate Similarity NPC212948
0.8105 Intermediate Similarity NPC234892
0.8105 Intermediate Similarity NPC195290
0.8105 Intermediate Similarity NPC204450
0.8101 Intermediate Similarity NPC235586
0.8095 Intermediate Similarity NPC271104
0.8095 Intermediate Similarity NPC469797
0.8095 Intermediate Similarity NPC37038
0.8095 Intermediate Similarity NPC469798
0.8095 Intermediate Similarity NPC104545
0.809 Intermediate Similarity NPC475921
0.809 Intermediate Similarity NPC168131
0.809 Intermediate Similarity NPC155479

  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 NPC164577 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
0.828 Intermediate Similarity NPD6404 Discontinued
0.8118 Intermediate Similarity NPD4221 Approved
0.8118 Intermediate Similarity NPD4223 Phase 3
0.8111 Intermediate Similarity NPD5281 Approved
0.8111 Intermediate Similarity NPD5284 Approved
0.8046 Intermediate Similarity NPD5329 Approved
0.7978 Intermediate Similarity NPD5737 Approved
0.7978 Intermediate Similarity NPD6672 Approved
0.7955 Intermediate Similarity NPD5690 Phase 2
0.7931 Intermediate Similarity NPD4197 Approved
0.7907 Intermediate Similarity NPD4752 Clinical (unspecified phase)
0.7889 Intermediate Similarity NPD6080 Approved
0.7889 Intermediate Similarity NPD6904 Approved
0.7889 Intermediate Similarity NPD6673 Approved
0.7872 Intermediate Similarity NPD6084 Phase 2
0.7872 Intermediate Similarity NPD6083 Phase 2
0.7849 Intermediate Similarity NPD5695 Phase 3
0.7826 Intermediate Similarity NPD6399 Phase 3
0.7753 Intermediate Similarity NPD3574 Clinical (unspecified phase)
0.7753 Intermediate Similarity NPD4690 Approved
0.7753 Intermediate Similarity NPD7146 Approved
0.7753 Intermediate Similarity NPD5205 Approved
0.7753 Intermediate Similarity NPD4694 Approved
0.7753 Intermediate Similarity NPD4519 Discontinued
0.7753 Intermediate Similarity NPD4693 Phase 3
0.7753 Intermediate Similarity NPD7334 Approved
0.7753 Intermediate Similarity NPD4138 Approved
0.7753 Intermediate Similarity NPD5280 Approved
0.7753 Intermediate Similarity NPD4623 Approved
0.7753 Intermediate Similarity NPD7521 Approved
0.7753 Intermediate Similarity NPD4689 Approved
0.7753 Intermediate Similarity NPD4688 Approved
0.7753 Intermediate Similarity NPD6409 Approved
0.7753 Intermediate Similarity NPD6684 Approved
0.7753 Intermediate Similarity NPD5330 Approved
0.7727 Intermediate Similarity NPD3133 Approved
0.7727 Intermediate Similarity NPD4786 Approved
0.7727 Intermediate Similarity NPD3666 Approved
0.7727 Intermediate Similarity NPD3665 Phase 1
0.7717 Intermediate Similarity NPD6050 Approved
0.7717 Intermediate Similarity NPD5693 Phase 1
0.7717 Intermediate Similarity NPD6079 Approved
0.7692 Intermediate Similarity NPD5328 Approved
0.7692 Intermediate Similarity NPD4753 Phase 2
0.7674 Intermediate Similarity NPD4695 Discontinued
0.7647 Intermediate Similarity NPD3617 Approved
0.7647 Intermediate Similarity NPD5784 Clinical (unspecified phase)
0.7609 Intermediate Similarity NPD5692 Phase 3
0.7604 Intermediate Similarity NPD5696 Approved
0.7582 Intermediate Similarity NPD5208 Approved
0.7582 Intermediate Similarity NPD7513 Clinical (unspecified phase)
0.7582 Intermediate Similarity NPD6903 Approved
0.7558 Intermediate Similarity NPD4195 Approved
0.7556 Intermediate Similarity NPD6098 Approved
0.7556 Intermediate Similarity NPD3618 Phase 1
0.7556 Intermediate Similarity NPD5279 Phase 3
0.7527 Intermediate Similarity NPD7515 Phase 2
0.7527 Intermediate Similarity NPD5694 Approved
0.7526 Intermediate Similarity NPD7640 Approved
0.7526 Intermediate Similarity NPD7639 Approved
0.75 Intermediate Similarity NPD7285 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD3667 Approved
0.7474 Intermediate Similarity NPD4629 Approved
0.7474 Intermediate Similarity NPD6356 Clinical (unspecified phase)
0.7474 Intermediate Similarity NPD5210 Approved
0.7439 Intermediate Similarity NPD4691 Approved
0.7439 Intermediate Similarity NPD4747 Approved
0.7423 Intermediate Similarity NPD7638 Approved
0.7419 Intermediate Similarity NPD5207 Approved
0.7396 Intermediate Similarity NPD5222 Approved
0.7396 Intermediate Similarity NPD5221 Approved
0.7396 Intermediate Similarity NPD5220 Clinical (unspecified phase)
0.7381 Intermediate Similarity NPD5733 Approved
0.7374 Intermediate Similarity NPD5211 Phase 2
0.7368 Intermediate Similarity NPD7748 Approved
0.7353 Intermediate Similarity NPD6899 Approved
0.7353 Intermediate Similarity NPD6881 Approved
0.7327 Intermediate Similarity NPD6402 Approved
0.7327 Intermediate Similarity NPD7128 Approved
0.7327 Intermediate Similarity NPD5739 Approved
0.7327 Intermediate Similarity NPD6675 Approved
0.732 Intermediate Similarity NPD5173 Approved
0.7317 Intermediate Similarity NPD4137 Phase 3
0.729 Intermediate Similarity NPD7115 Discovery
0.7263 Intermediate Similarity NPD4202 Approved
0.7255 Intermediate Similarity NPD5697 Approved
0.7253 Intermediate Similarity NPD7520 Clinical (unspecified phase)
0.7253 Intermediate Similarity NPD5363 Approved
0.7234 Intermediate Similarity NPD5785 Approved
0.7234 Intermediate Similarity NPD4096 Approved
0.7228 Intermediate Similarity NPD5141 Approved
0.7222 Intermediate Similarity NPD4788 Approved
0.7222 Intermediate Similarity NPD5362 Discontinued
0.7216 Intermediate Similarity NPD4697 Phase 3
0.7216 Intermediate Similarity NPD7614 Phase 1
0.7212 Intermediate Similarity NPD7102 Approved
0.7212 Intermediate Similarity NPD6883 Approved
0.7212 Intermediate Similarity NPD7290 Approved
0.7191 Intermediate Similarity NPD4692 Approved
0.7191 Intermediate Similarity NPD4139 Approved
0.7188 Intermediate Similarity NPD6001 Approved
0.7184 Intermediate Similarity NPD7320 Approved
0.7184 Intermediate Similarity NPD6011 Approved
0.7176 Intermediate Similarity NPD4687 Approved
0.7176 Intermediate Similarity NPD4058 Approved
0.7172 Intermediate Similarity NPD5286 Approved
0.7172 Intermediate Similarity NPD4696 Approved
0.7172 Intermediate Similarity NPD5285 Approved
0.7143 Intermediate Similarity NPD8130 Phase 1
0.7143 Intermediate Similarity NPD4755 Approved
0.7143 Intermediate Similarity NPD6869 Approved
0.7143 Intermediate Similarity NPD6617 Approved
0.7143 Intermediate Similarity NPD7902 Approved
0.7143 Intermediate Similarity NPD5276 Approved
0.7143 Intermediate Similarity NPD6650 Approved
0.7143 Intermediate Similarity NPD6847 Approved
0.7143 Intermediate Similarity NPD4243 Approved
0.7143 Intermediate Similarity NPD6649 Approved
0.7143 Intermediate Similarity NPD3668 Phase 3
0.7115 Intermediate Similarity NPD6013 Approved
0.7115 Intermediate Similarity NPD6373 Approved
0.7115 Intermediate Similarity NPD6372 Approved
0.7115 Intermediate Similarity NPD6014 Approved
0.7115 Intermediate Similarity NPD6012 Approved
0.7113 Intermediate Similarity NPD5654 Approved
0.71 Intermediate Similarity NPD5223 Approved
0.7097 Intermediate Similarity NPD3573 Approved
0.7087 Intermediate Similarity NPD5701 Approved
0.7083 Intermediate Similarity NPD5133 Approved
0.7075 Intermediate Similarity NPD6882 Approved
0.7075 Intermediate Similarity NPD8297 Approved
0.7065 Intermediate Similarity NPD1694 Approved
0.703 Intermediate Similarity NPD5224 Approved
0.703 Intermediate Similarity NPD5226 Approved
0.703 Intermediate Similarity NPD5091 Approved
0.703 Intermediate Similarity NPD5225 Approved
0.703 Intermediate Similarity NPD4633 Approved
0.7021 Intermediate Similarity NPD4518 Approved
0.7 Intermediate Similarity NPD4700 Approved
0.6981 Remote Similarity NPD6401 Clinical (unspecified phase)
0.6979 Remote Similarity NPD8035 Phase 2
0.6979 Remote Similarity NPD8034 Phase 2
0.6979 Remote Similarity NPD7637 Suspended
0.6977 Remote Similarity NPD4784 Approved
0.6977 Remote Similarity NPD4785 Approved
0.697 Remote Similarity NPD5959 Approved
0.6961 Remote Similarity NPD5175 Approved
0.6961 Remote Similarity NPD5174 Approved
0.6961 Remote Similarity NPD6052 Approved
0.6947 Remote Similarity NPD6051 Approved
0.6941 Remote Similarity NPD6081 Approved
0.6923 Remote Similarity NPD4270 Approved
0.6923 Remote Similarity NPD6614 Approved
0.6923 Remote Similarity NPD4269 Approved
0.69 Remote Similarity NPD4225 Approved
0.6897 Remote Similarity NPD7339 Approved
0.6897 Remote Similarity NPD6942 Approved
0.6881 Remote Similarity NPD6868 Approved
0.6863 Remote Similarity NPD7632 Discontinued
0.6857 Remote Similarity NPD6686 Approved
0.6852 Remote Similarity NPD4632 Approved
0.6848 Remote Similarity NPD5331 Approved
0.6848 Remote Similarity NPD5332 Approved
0.6837 Remote Similarity NPD7901 Clinical (unspecified phase)
0.6837 Remote Similarity NPD7900 Approved
0.6813 Remote Similarity NPD4790 Discontinued
0.6796 Remote Similarity NPD4754 Approved
0.6786 Remote Similarity NPD3621 Clinical (unspecified phase)
0.6762 Remote Similarity NPD6412 Phase 2
0.6759 Remote Similarity NPD6053 Discontinued
0.6757 Remote Similarity NPD6335 Approved
0.6747 Remote Similarity NPD4224 Phase 2
0.6747 Remote Similarity NPD7331 Phase 2
0.6735 Remote Similarity NPD5778 Approved
0.6735 Remote Similarity NPD5779 Approved
0.6727 Remote Similarity NPD6274 Approved
0.6705 Remote Similarity NPD8039 Approved
0.6705 Remote Similarity NPD5275 Approved
0.6705 Remote Similarity NPD4190 Phase 3
0.6703 Remote Similarity NPD4821 Approved
0.6703 Remote Similarity NPD4252 Approved
0.6703 Remote Similarity NPD4819 Approved
0.6703 Remote Similarity NPD7525 Registered
0.6703 Remote Similarity NPD4820 Approved
0.6703 Remote Similarity NPD4822 Approved
0.67 Remote Similarity NPD7732 Phase 3
0.6698 Remote Similarity NPD5168 Approved
0.6698 Remote Similarity NPD4730 Approved
0.6698 Remote Similarity NPD4729 Approved
0.6698 Remote Similarity NPD5128 Approved
0.6696 Remote Similarity NPD7100 Approved
0.6696 Remote Similarity NPD7101 Approved
0.6667 Remote Similarity NPD4767 Approved
0.6667 Remote Similarity NPD4192 Approved
0.6667 Remote Similarity NPD4768 Approved
0.6667 Remote Similarity NPD6008 Approved
0.6667 Remote Similarity NPD4194 Approved
0.6667 Remote Similarity NPD6009 Approved
0.6667 Remote Similarity NPD6317 Approved
0.6667 Remote Similarity NPD7154 Phase 3

  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