Structure

Physi-Chem Properties

Molecular Weight:  358.14
Volume:  363.093
LogP:  1.26
LogD:  1.261
LogS:  -3.273
# Rotatable Bonds:  3
TPSA:  86.74
# H-Bond Aceptor:  6
# H-Bond Donor:  0
# Rings:  3
# Heavy Atoms:  6

MedChem Properties

QED Drug-Likeness Score:  0.556
Synthetic Accessibility Score:  4.706
Fsp3:  0.5
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Accepted
BMS Rule:  2
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.782
MDCK Permeability:  2.7395502911531366e-05
Pgp-inhibitor:  0.974
Pgp-substrate:  0.001
Human Intestinal Absorption (HIA):  0.006
20% Bioavailability (F20%):  0.982
30% Bioavailability (F30%):  0.593

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.884
Plasma Protein Binding (PPB):  70.98787689208984%
Volume Distribution (VD):  0.592
Pgp-substrate:  26.95847511291504%

ADMET: Metabolism

CYP1A2-inhibitor:  0.462
CYP1A2-substrate:  0.541
CYP2C19-inhibitor:  0.877
CYP2C19-substrate:  0.69
CYP2C9-inhibitor:  0.784
CYP2C9-substrate:  0.07
CYP2D6-inhibitor:  0.314
CYP2D6-substrate:  0.066
CYP3A4-inhibitor:  0.861
CYP3A4-substrate:  0.319

ADMET: Excretion

Clearance (CL):  8.796
Half-life (T1/2):  0.798

ADMET: Toxicity

hERG Blockers:  0.004
Human Hepatotoxicity (H-HT):  0.168
Drug-inuced Liver Injury (DILI):  0.591
AMES Toxicity:  0.047
Rat Oral Acute Toxicity:  0.601
Maximum Recommended Daily Dose:  0.481
Skin Sensitization:  0.652
Carcinogencity:  0.383
Eye Corrosion:  0.315
Eye Irritation:  0.332
Respiratory Toxicity:  0.806

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

  Natural Product: NPC54843

Natural Product ID:  NPC54843
Common Name*:   Multistatin
IUPAC Name:   [(3aS,5S,5aS,8aR,9S,9aS)-5,8a-dimethyl-1-methylidene-2,4,8-trioxo-5,5a,9,9a-tetrahydro-3aH-azuleno[6,5-b]furan-9-yl] (Z)-2-methylbut-2-enoate
Synonyms:   Multistatin
Standard InCHIKey:  YPIMMVOHCVOXKT-CXMZHGGDSA-N
Standard InCHI:  InChI=1S/C20H22O6/c1-6-9(2)18(23)26-17-14-11(4)19(24)25-16(14)15(22)10(3)12-7-8-13(21)20(12,17)5/h6-8,10,12,14,16-17H,4H2,1-3,5H3/b9-6-/t10-,12-,14+,16-,17-,20-/m0/s1
SMILES:  C/C=C(/C)C(=O)O[C@H]1[C@@H]2C(=C)C(=O)O[C@@H]2C(=O)[C@@H](C)[C@@H]2C=CC(=O)[C@@]12C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL516983
PubChem CID:   5319944
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0000259] Prenol lipids
        • [CHEMONTID:0001283] Terpene lactones
          • [CHEMONTID:0001543] Sesquiterpene lactones

*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
NPO29365 Baileya multiradiata Species Asteraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO29365 Baileya multiradiata Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO29365 Baileya multiradiata Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO29365 Baileya multiradiata 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
NPT168 Cell Line P388 Mus musculus T/C = 131.0 n.a. PMID[553991]
NPT368 Cell Line SN12C Homo sapiens GI50 n.a. 1419.06 nM PMID[553992]
NPT367 Cell Line MDA-N Homo sapiens GI50 n.a. 674.53 nM PMID[553992]
NPT369 Cell Line ACHN Homo sapiens GI50 n.a. 212.32 nM PMID[553992]
NPT370 Cell Line NCI-H23 Homo sapiens GI50 n.a. 2877.4 nM PMID[553992]
NPT371 Cell Line UO-31 Homo sapiens GI50 n.a. 1205.04 nM PMID[553992]
NPT372 Cell Line HOP-92 Homo sapiens GI50 n.a. 392.64 nM PMID[553992]
NPT116 Cell Line HL-60 Homo sapiens GI50 n.a. 132.13 nM PMID[553992]
NPT374 Cell Line SF-539 Homo sapiens GI50 n.a. 1840.77 nM PMID[553992]
NPT90 Cell Line DU-145 Homo sapiens GI50 n.a. 1570.36 nM PMID[553992]
NPT375 Cell Line Malme-3M Homo sapiens GI50 n.a. 297.85 nM PMID[553992]
NPT373 Cell Line SK-MEL-5 Homo sapiens GI50 n.a. 1678.8 nM PMID[553992]
NPT376 Cell Line A498 Homo sapiens GI50 n.a. 1690.44 nM PMID[553992]
NPT111 Cell Line K562 Homo sapiens GI50 n.a. 293.09 nM PMID[553992]
NPT377 Cell Line OVCAR-3 Homo sapiens GI50 n.a. 653.13 nM PMID[553992]
NPT112 Cell Line MOLT-4 Homo sapiens GI50 n.a. 410.2 nM PMID[553992]
NPT379 Cell Line HOP-62 Homo sapiens GI50 n.a. 11912.42 nM PMID[553992]
NPT378 Cell Line NCI/ADR-RES Homo sapiens GI50 n.a. 2371.37 nM PMID[553992]
NPT380 Cell Line U-251 Homo sapiens GI50 n.a. 2426.61 nM PMID[553992]
NPT381 Cell Line OVCAR-8 Homo sapiens GI50 n.a. 1725.84 nM PMID[553992]
NPT382 Cell Line OVCAR-5 Homo sapiens GI50 n.a. 2223.31 nM PMID[553992]
NPT82 Cell Line MDA-MB-231 Homo sapiens GI50 n.a. 1883.65 nM PMID[553992]
NPT383 Cell Line SNB-19 Homo sapiens GI50 n.a. 12852.87 nM PMID[553992]
NPT384 Cell Line TK-10 Homo sapiens GI50 n.a. 538.27 nM PMID[553992]
NPT385 Cell Line SR Homo sapiens GI50 n.a. 223.36 nM PMID[553992]
NPT323 Cell Line SW-620 Homo sapiens GI50 n.a. 361.41 nM PMID[553992]
NPT455 Cell Line NCI-H522 Homo sapiens GI50 n.a. 88.31 nM PMID[553992]
NPT386 Cell Line KM12 Homo sapiens GI50 n.a. 2301.44 nM PMID[553992]
NPT387 Cell Line M14 Homo sapiens GI50 n.a. 1563.15 nM PMID[553992]
NPT388 Cell Line NCI-H322M Homo sapiens GI50 n.a. 13243.42 nM PMID[553992]
NPT389 Cell Line RPMI-8226 Homo sapiens GI50 n.a. 326.59 nM PMID[553992]
NPT456 Cell Line OVCAR-4 Homo sapiens GI50 n.a. 5035.01 nM PMID[553992]
NPT390 Cell Line LOX IMVI Homo sapiens GI50 n.a. 554.63 nM PMID[553992]
NPT457 Cell Line BT-549 Homo sapiens GI50 n.a. 688.65 nM PMID[553992]
NPT147 Cell Line SK-MEL-2 Homo sapiens GI50 n.a. 2857.59 nM PMID[553992]
NPT81 Cell Line A549 Homo sapiens GI50 n.a. 10641.43 nM PMID[553992]
NPT391 Cell Line HCC 2998 Homo sapiens GI50 n.a. 1713.96 nM PMID[553992]
NPT392 Cell Line SNB-75 Homo sapiens GI50 n.a. 5533.5 nM PMID[553992]
NPT148 Cell Line HCT-15 Homo sapiens GI50 n.a. 283.79 nM PMID[553992]
NPT393 Cell Line HCT-116 Homo sapiens GI50 n.a. 237.68 nM PMID[553992]
NPT395 Cell Line SF-268 Homo sapiens GI50 n.a. 1690.44 nM PMID[553992]
NPT394 Cell Line EKVX Homo sapiens GI50 n.a. 1104.08 nM PMID[553992]
NPT306 Cell Line PC-3 Homo sapiens GI50 n.a. 2285.6 nM PMID[553992]
NPT83 Cell Line MCF7 Homo sapiens GI50 n.a. 394.46 nM PMID[553992]
NPT146 Cell Line SK-OV-3 Homo sapiens GI50 n.a. 13122.0 nM PMID[553992]
NPT397 Cell Line NCI-H460 Homo sapiens GI50 n.a. 2208.0 nM PMID[553992]
NPT396 Cell Line T47D Homo sapiens GI50 n.a. 483.06 nM PMID[553992]
NPT308 Cell Line CAKI-1 Homo sapiens GI50 n.a. 264.24 nM PMID[553992]
NPT398 Cell Line UACC-62 Homo sapiens GI50 n.a. 1253.14 nM PMID[553992]
NPT400 Cell Line MDA-MB-435 Homo sapiens GI50 n.a. 1291.22 nM PMID[553992]
NPT458 Cell Line IGROV-1 Homo sapiens GI50 n.a. 1482.52 nM PMID[553992]
NPT399 Cell Line SF-295 Homo sapiens GI50 n.a. 13001.7 nM PMID[553992]
NPT402 Cell Line Hs-578T Homo sapiens GI50 n.a. 6441.69 nM PMID[553992]
NPT401 Cell Line 786-0 Homo sapiens GI50 n.a. 310.46 nM PMID[553992]
NPT403 Cell Line UACC-257 Homo sapiens GI50 n.a. 1472.31 nM PMID[553992]
NPT404 Cell Line CCRF-CEM Homo sapiens GI50 n.a. 167.88 nM PMID[553992]
NPT139 Cell Line HT-29 Homo sapiens GI50 n.a. 370.68 nM PMID[553992]
NPT405 Cell Line NCI-H226 Homo sapiens GI50 n.a. 2376.84 nM PMID[553992]
NPT170 Cell Line SK-MEL-28 Homo sapiens GI50 n.a. 277.97 nM PMID[553992]
NPT406 Cell Line RXF 393 Homo sapiens GI50 n.a. 378.44 nM PMID[553992]
NPT407 Cell Line COLO 205 Homo sapiens GI50 n.a. 237.14 nM PMID[553992]

☑ 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 NPC54843 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
0.9341 High Similarity NPC74103
0.9341 High Similarity NPC150978
0.9341 High Similarity NPC284185
0.9341 High Similarity NPC70595
0.9341 High Similarity NPC123177
0.9231 High Similarity NPC253144
0.8958 High Similarity NPC141191
0.8854 High Similarity NPC169205
0.8842 High Similarity NPC275960
0.8842 High Similarity NPC48803
0.8842 High Similarity NPC193645
0.8842 High Similarity NPC90121
0.8791 High Similarity NPC104961
0.8791 High Similarity NPC70555
0.8791 High Similarity NPC70422
0.875 High Similarity NPC185553
0.8681 High Similarity NPC161957
0.8681 High Similarity NPC33570
0.8681 High Similarity NPC21471
0.8646 High Similarity NPC474490
0.8542 High Similarity NPC167219
0.8515 High Similarity NPC203659
0.8462 Intermediate Similarity NPC39588
0.8416 Intermediate Similarity NPC110989
0.8404 Intermediate Similarity NPC469653
0.8404 Intermediate Similarity NPC471047
0.8404 Intermediate Similarity NPC469631
0.8404 Intermediate Similarity NPC469628
0.8404 Intermediate Similarity NPC475906
0.8387 Intermediate Similarity NPC279859
0.8387 Intermediate Similarity NPC238593
0.8387 Intermediate Similarity NPC38576
0.8387 Intermediate Similarity NPC107787
0.8333 Intermediate Similarity NPC111114
0.8333 Intermediate Similarity NPC300312
0.8333 Intermediate Similarity NPC261607
0.8317 Intermediate Similarity NPC225353
0.8316 Intermediate Similarity NPC117405
0.8316 Intermediate Similarity NPC52198
0.828 Intermediate Similarity NPC78089
0.8261 Intermediate Similarity NPC215294
0.8247 Intermediate Similarity NPC475302
0.8235 Intermediate Similarity NPC475945
0.8235 Intermediate Similarity NPC475871
0.8235 Intermediate Similarity NPC475873
0.8218 Intermediate Similarity NPC474742
0.8211 Intermediate Similarity NPC475902
0.8182 Intermediate Similarity NPC476275
0.8172 Intermediate Similarity NPC115786
0.8163 Intermediate Similarity NPC148463
0.8163 Intermediate Similarity NPC289004
0.8155 Intermediate Similarity NPC472756
0.8155 Intermediate Similarity NPC474741
0.8152 Intermediate Similarity NPC173609
0.8144 Intermediate Similarity NPC20713
0.8137 Intermediate Similarity NPC474747
0.8132 Intermediate Similarity NPC223904
0.8081 Intermediate Similarity NPC474947
0.8065 Intermediate Similarity NPC54468
0.8065 Intermediate Similarity NPC474703
0.8061 Intermediate Similarity NPC165383
0.8043 Intermediate Similarity NPC25684
0.8043 Intermediate Similarity NPC301477
0.8043 Intermediate Similarity NPC281949
0.8041 Intermediate Similarity NPC329857
0.8041 Intermediate Similarity NPC471818
0.8041 Intermediate Similarity NPC62815
0.8041 Intermediate Similarity NPC469718
0.8039 Intermediate Similarity NPC185141
0.8039 Intermediate Similarity NPC110443
0.8039 Intermediate Similarity NPC171759
0.8039 Intermediate Similarity NPC46998
0.8039 Intermediate Similarity NPC128733
0.8039 Intermediate Similarity NPC472753
0.8039 Intermediate Similarity NPC133907
0.798 Intermediate Similarity NPC469632
0.7961 Intermediate Similarity NPC472754
0.7959 Intermediate Similarity NPC286341
0.7959 Intermediate Similarity NPC191339
0.7938 Intermediate Similarity NPC168679
0.7938 Intermediate Similarity NPC12872
0.7935 Intermediate Similarity NPC69271
0.7935 Intermediate Similarity NPC74673
0.7921 Intermediate Similarity NPC170143
0.7921 Intermediate Similarity NPC108475
0.7921 Intermediate Similarity NPC213947
0.79 Intermediate Similarity NPC304886
0.7885 Intermediate Similarity NPC472755
0.7879 Intermediate Similarity NPC135776
0.7864 Intermediate Similarity NPC473384
0.7864 Intermediate Similarity NPC477950
0.7857 Intermediate Similarity NPC129419
0.7849 Intermediate Similarity NPC39411
0.7849 Intermediate Similarity NPC35089
0.7849 Intermediate Similarity NPC10276
0.7849 Intermediate Similarity NPC255580
0.7822 Intermediate Similarity NPC121036
0.7822 Intermediate Similarity NPC472674
0.78 Intermediate Similarity NPC140543
0.78 Intermediate Similarity NPC477131
0.78 Intermediate Similarity NPC121825
0.78 Intermediate Similarity NPC476267
0.78 Intermediate Similarity NPC476596
0.7788 Intermediate Similarity NPC149371
0.7778 Intermediate Similarity NPC219874
0.7755 Intermediate Similarity NPC268298
0.7742 Intermediate Similarity NPC290508
0.7742 Intermediate Similarity NPC73052
0.7742 Intermediate Similarity NPC293418
0.7742 Intermediate Similarity NPC276356
0.7742 Intermediate Similarity NPC6823
0.7742 Intermediate Similarity NPC302426
0.7732 Intermediate Similarity NPC471739
0.7732 Intermediate Similarity NPC478144
0.7714 Intermediate Similarity NPC271059
0.7714 Intermediate Similarity NPC25666
0.7708 Intermediate Similarity NPC96621
0.77 Intermediate Similarity NPC476598
0.77 Intermediate Similarity NPC469692
0.77 Intermediate Similarity NPC469645
0.77 Intermediate Similarity NPC476597
0.7692 Intermediate Similarity NPC47880
0.7692 Intermediate Similarity NPC264477
0.7692 Intermediate Similarity NPC477511
0.7692 Intermediate Similarity NPC476270
0.7684 Intermediate Similarity NPC318468
0.7684 Intermediate Similarity NPC475947
0.7679 Intermediate Similarity NPC471146
0.7679 Intermediate Similarity NPC471145
0.767 Intermediate Similarity NPC470188
0.7664 Intermediate Similarity NPC26617
0.766 Intermediate Similarity NPC471325
0.766 Intermediate Similarity NPC275507
0.766 Intermediate Similarity NPC141810
0.7652 Intermediate Similarity NPC192309
0.7647 Intermediate Similarity NPC126156
0.7647 Intermediate Similarity NPC301596
0.7647 Intermediate Similarity NPC17585
0.7647 Intermediate Similarity NPC91771
0.7647 Intermediate Similarity NPC142529
0.7647 Intermediate Similarity NPC172998
0.7647 Intermediate Similarity NPC299396
0.7647 Intermediate Similarity NPC184065
0.7642 Intermediate Similarity NPC477510
0.7642 Intermediate Similarity NPC471143
0.7642 Intermediate Similarity NPC100487
0.7642 Intermediate Similarity NPC309190
0.7634 Intermediate Similarity NPC178277
0.7634 Intermediate Similarity NPC270126
0.7632 Intermediate Similarity NPC147635
0.7632 Intermediate Similarity NPC163693
0.7629 Intermediate Similarity NPC261721
0.7629 Intermediate Similarity NPC64153
0.7629 Intermediate Similarity NPC284902
0.7624 Intermediate Similarity NPC473331
0.7619 Intermediate Similarity NPC105725
0.7609 Intermediate Similarity NPC65603
0.7609 Intermediate Similarity NPC476794
0.7609 Intermediate Similarity NPC470240
0.7604 Intermediate Similarity NPC149869
0.7604 Intermediate Similarity NPC238197
0.76 Intermediate Similarity NPC133698
0.76 Intermediate Similarity NPC221282
0.7596 Intermediate Similarity NPC477512
0.7586 Intermediate Similarity NPC42747
0.7586 Intermediate Similarity NPC1538
0.7579 Intermediate Similarity NPC471326
0.7579 Intermediate Similarity NPC221231
0.7576 Intermediate Similarity NPC32922
0.7576 Intermediate Similarity NPC166919
0.7551 Intermediate Similarity NPC201658
0.7551 Intermediate Similarity NPC72513
0.7551 Intermediate Similarity NPC478145
0.7551 Intermediate Similarity NPC475703
0.7551 Intermediate Similarity NPC237540
0.7551 Intermediate Similarity NPC266957
0.7549 Intermediate Similarity NPC470978
0.7549 Intermediate Similarity NPC475900
0.7549 Intermediate Similarity NPC470974
0.7549 Intermediate Similarity NPC234339
0.7549 Intermediate Similarity NPC273197
0.7547 Intermediate Similarity NPC472747
0.7547 Intermediate Similarity NPC472750
0.7545 Intermediate Similarity NPC475495
0.7527 Intermediate Similarity NPC128276
0.7526 Intermediate Similarity NPC290329
0.7526 Intermediate Similarity NPC125290
0.7526 Intermediate Similarity NPC165162
0.7526 Intermediate Similarity NPC155873
0.7526 Intermediate Similarity NPC472686
0.7525 Intermediate Similarity NPC473234
0.7525 Intermediate Similarity NPC202824
0.7525 Intermediate Similarity NPC60386
0.7525 Intermediate Similarity NPC308656
0.7525 Intermediate Similarity NPC477361
0.7525 Intermediate Similarity NPC473263
0.7525 Intermediate Similarity NPC473273
0.7525 Intermediate Similarity NPC153590
0.7524 Intermediate Similarity NPC474339
0.7524 Intermediate Similarity NPC201718

  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 NPC54843 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
0.8842 High Similarity NPD1698 Clinical (unspecified phase)
0.7664 Intermediate Similarity NPD7899 Clinical (unspecified phase)
0.7451 Intermediate Similarity NPD5282 Discontinued
0.74 Intermediate Similarity NPD1695 Approved
0.7396 Intermediate Similarity NPD5209 Approved
0.7347 Intermediate Similarity NPD1694 Approved
0.7327 Intermediate Similarity NPD5785 Approved
0.7297 Intermediate Similarity NPD6371 Approved
0.7041 Intermediate Similarity NPD4752 Clinical (unspecified phase)
0.6852 Remote Similarity NPD4225 Approved
0.6832 Remote Similarity NPD5363 Approved
0.6832 Remote Similarity NPD1733 Clinical (unspecified phase)
0.6765 Remote Similarity NPD5786 Approved
0.6726 Remote Similarity NPD5697 Approved
0.6697 Remote Similarity NPD5696 Approved
0.6667 Remote Similarity NPD6899 Approved
0.6667 Remote Similarity NPD6881 Approved
0.6638 Remote Similarity NPD6650 Approved
0.6638 Remote Similarity NPD6649 Approved
0.6635 Remote Similarity NPD5737 Approved
0.6635 Remote Similarity NPD6672 Approved
0.6609 Remote Similarity NPD6014 Approved
0.6609 Remote Similarity NPD6013 Approved
0.6609 Remote Similarity NPD6012 Approved
0.6604 Remote Similarity NPD6411 Approved
0.6604 Remote Similarity NPD5693 Phase 1
0.6552 Remote Similarity NPD7102 Approved
0.6552 Remote Similarity NPD7290 Approved
0.6552 Remote Similarity NPD6883 Approved
0.6542 Remote Similarity NPD5779 Approved
0.6542 Remote Similarity NPD5778 Approved
0.6535 Remote Similarity NPD4270 Approved
0.6535 Remote Similarity NPD6435 Approved
0.6535 Remote Similarity NPD4269 Approved
0.6522 Remote Similarity NPD6011 Approved
0.6522 Remote Similarity NPD7320 Approved
0.65 Remote Similarity NPD7115 Discovery
0.6496 Remote Similarity NPD6617 Approved
0.6496 Remote Similarity NPD8130 Phase 1
0.6496 Remote Similarity NPD6847 Approved
0.6496 Remote Similarity NPD6869 Approved
0.6491 Remote Similarity NPD5739 Approved
0.6491 Remote Similarity NPD6008 Approved
0.6491 Remote Similarity NPD6675 Approved
0.6491 Remote Similarity NPD6402 Approved
0.6491 Remote Similarity NPD7128 Approved
0.6471 Remote Similarity NPD7154 Phase 3
0.6471 Remote Similarity NPD5362 Discontinued
0.6466 Remote Similarity NPD6372 Approved
0.6466 Remote Similarity NPD6373 Approved
0.6449 Remote Similarity NPD7983 Approved
0.6441 Remote Similarity NPD8297 Approved
0.6441 Remote Similarity NPD6882 Approved
0.6436 Remote Similarity NPD5369 Approved
0.6435 Remote Similarity NPD5701 Approved
0.6422 Remote Similarity NPD5695 Phase 3
0.6415 Remote Similarity NPD5764 Clinical (unspecified phase)
0.6415 Remote Similarity NPD6101 Approved
0.64 Remote Similarity NPD7492 Approved
0.6357 Remote Similarity NPD7260 Phase 2
0.6355 Remote Similarity NPD6698 Approved
0.6355 Remote Similarity NPD46 Approved
0.6349 Remote Similarity NPD6616 Approved
0.6341 Remote Similarity NPD6319 Approved
0.6341 Remote Similarity NPD6054 Approved
0.6337 Remote Similarity NPD5368 Approved
0.6337 Remote Similarity NPD4252 Approved
0.6327 Remote Similarity NPD8039 Approved
0.6321 Remote Similarity NPD6903 Approved
0.6306 Remote Similarity NPD6083 Phase 2
0.6306 Remote Similarity NPD6084 Phase 2
0.6303 Remote Similarity NPD6053 Discontinued
0.63 Remote Similarity NPD5784 Clinical (unspecified phase)
0.6299 Remote Similarity NPD7078 Approved
0.6296 Remote Similarity NPD5694 Approved
0.629 Remote Similarity NPD6016 Approved
0.629 Remote Similarity NPD6015 Approved
0.6286 Remote Similarity NPD6409 Approved
0.6286 Remote Similarity NPD7334 Approved
0.6286 Remote Similarity NPD5330 Approved
0.6286 Remote Similarity NPD6684 Approved
0.6286 Remote Similarity NPD7146 Approved
0.6286 Remote Similarity NPD7521 Approved
0.6273 Remote Similarity NPD4629 Approved
0.6273 Remote Similarity NPD5210 Approved
0.6262 Remote Similarity NPD6673 Approved
0.6262 Remote Similarity NPD6080 Approved
0.6262 Remote Similarity NPD6904 Approved
0.625 Remote Similarity NPD7736 Approved
0.624 Remote Similarity NPD5988 Approved
0.624 Remote Similarity NPD6370 Approved
0.6239 Remote Similarity NPD6399 Phase 3
0.6239 Remote Similarity NPD6686 Approved
0.6228 Remote Similarity NPD5211 Phase 2
0.6226 Remote Similarity NPD3573 Approved
0.6214 Remote Similarity NPD4800 Clinical (unspecified phase)
0.6204 Remote Similarity NPD5692 Phase 3
0.6204 Remote Similarity NPD7838 Discovery
0.6204 Remote Similarity NPD5207 Approved
0.6195 Remote Similarity NPD5286 Approved
0.6195 Remote Similarity NPD5285 Approved
0.6195 Remote Similarity NPD4696 Approved
0.619 Remote Similarity NPD6082 Clinical (unspecified phase)
0.6183 Remote Similarity NPD6845 Suspended
0.6182 Remote Similarity NPD7901 Clinical (unspecified phase)
0.6182 Remote Similarity NPD7900 Approved
0.6176 Remote Similarity NPD5790 Clinical (unspecified phase)
0.6168 Remote Similarity NPD7513 Clinical (unspecified phase)
0.616 Remote Similarity NPD6291 Clinical (unspecified phase)
0.6154 Remote Similarity NPD6614 Approved
0.6148 Remote Similarity NPD6274 Approved
0.6147 Remote Similarity NPD6050 Approved
0.6132 Remote Similarity NPD4249 Approved
0.6129 Remote Similarity NPD7100 Approved
0.6129 Remote Similarity NPD7101 Approved
0.6126 Remote Similarity NPD6356 Clinical (unspecified phase)
0.6121 Remote Similarity NPD5141 Approved
0.6119 Remote Similarity NPD7966 Clinical (unspecified phase)
0.6102 Remote Similarity NPD5345 Clinical (unspecified phase)
0.6098 Remote Similarity NPD6317 Approved
0.6087 Remote Similarity NPD5225 Approved
0.6087 Remote Similarity NPD5224 Approved
0.6087 Remote Similarity NPD4633 Approved
0.6087 Remote Similarity NPD5226 Approved
0.6083 Remote Similarity NPD6401 Clinical (unspecified phase)
0.6083 Remote Similarity NPD8413 Clinical (unspecified phase)
0.608 Remote Similarity NPD6059 Approved
0.6075 Remote Similarity NPD4250 Approved
0.6075 Remote Similarity NPD4251 Approved
0.6071 Remote Similarity NPD7839 Suspended
0.6071 Remote Similarity NPD5221 Approved
0.6071 Remote Similarity NPD5220 Clinical (unspecified phase)
0.6071 Remote Similarity NPD5222 Approved
0.6064 Remote Similarity NPD2685 Clinical (unspecified phase)
0.6048 Remote Similarity NPD6314 Approved
0.6048 Remote Similarity NPD6313 Approved
0.6048 Remote Similarity NPD6335 Approved
0.6047 Remote Similarity NPD8293 Discontinued
0.604 Remote Similarity NPD4756 Discovery
0.6034 Remote Similarity NPD5175 Approved
0.6034 Remote Similarity NPD5174 Approved
0.6019 Remote Similarity NPD4695 Discontinued
0.6019 Remote Similarity NPD4820 Approved
0.6019 Remote Similarity NPD4822 Approved
0.6019 Remote Similarity NPD4819 Approved
0.6019 Remote Similarity NPD4821 Approved
0.6018 Remote Similarity NPD7902 Approved
0.6018 Remote Similarity NPD5173 Approved
0.6018 Remote Similarity NPD4755 Approved
0.6016 Remote Similarity NPD6868 Approved
0.6 Remote Similarity NPD4634 Approved
0.6 Remote Similarity NPD7637 Suspended
0.6 Remote Similarity NPD5223 Approved
0.6 Remote Similarity NPD2067 Discontinued
0.5984 Remote Similarity NPD4632 Approved
0.5981 Remote Similarity NPD6098 Approved
0.598 Remote Similarity NPD4271 Approved
0.598 Remote Similarity NPD4268 Approved
0.5968 Remote Similarity NPD6009 Approved
0.5965 Remote Similarity NPD7638 Approved
0.5938 Remote Similarity NPD8328 Phase 3
0.5929 Remote Similarity NPD4697 Phase 3
0.5913 Remote Similarity NPD7639 Approved
0.5913 Remote Similarity NPD7640 Approved
0.5913 Remote Similarity NPD4700 Approved
0.5906 Remote Similarity NPD8517 Approved
0.5906 Remote Similarity NPD8516 Approved
0.5906 Remote Similarity NPD8515 Approved
0.5906 Remote Similarity NPD5983 Phase 2
0.5906 Remote Similarity NPD8513 Phase 3
0.5893 Remote Similarity NPD7748 Approved
0.5893 Remote Similarity NPD6001 Approved
0.5882 Remote Similarity NPD5954 Clinical (unspecified phase)
0.5856 Remote Similarity NPD6079 Approved
0.5856 Remote Similarity NPD5284 Approved
0.5856 Remote Similarity NPD5281 Approved
0.5849 Remote Similarity NPD5332 Approved
0.5849 Remote Similarity NPD5331 Approved
0.5841 Remote Similarity NPD5654 Approved
0.5833 Remote Similarity NPD7319 Approved
0.5833 Remote Similarity NPD4730 Approved
0.5833 Remote Similarity NPD4729 Approved
0.5833 Remote Similarity NPD5279 Phase 3
0.5833 Remote Similarity NPD6108 Clinical (unspecified phase)
0.5826 Remote Similarity NPD8029 Clinical (unspecified phase)
0.582 Remote Similarity NPD2204 Approved
0.5818 Remote Similarity NPD4753 Phase 2
0.5818 Remote Similarity NPD5370 Suspended
0.5814 Remote Similarity NPD7604 Phase 2
0.581 Remote Similarity NPD4790 Discontinued
0.5794 Remote Similarity NPD6400 Clinical (unspecified phase)
0.5789 Remote Similarity NPD7732 Phase 3
0.5781 Remote Similarity NPD6908 Approved
0.5781 Remote Similarity NPD6909 Approved
0.5776 Remote Similarity NPD6648 Approved
0.5741 Remote Similarity NPD1696 Phase 3
0.5739 Remote Similarity NPD5959 Approved
0.5738 Remote Similarity NPD5250 Approved
0.5738 Remote Similarity NPD5247 Approved
0.5738 Remote Similarity NPD5249 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