NPASS Compound

Structure

NPC226049 OpenBabel07101719522D 42 50 0 0 1 0 0 0 0 0999 V2000 -1.7600 -1.8969 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.1408 -0.6098 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3135 0.8329 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0107 2.1274 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3022 0.2556 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0160 -1.3004 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9132 3.5985 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1372 1.1300 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2295 -2.0961 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8026 -2.0961 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2343 -1.0462 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.4498 -1.5609 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9715 -0.4872 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5385 -1.1451 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4935 -1.1451 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.4935 0.1706 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.7202 -0.8938 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.3118 -0.8938 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3498 2.7722 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.3471 2.6975 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.0160 0.3259 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6135 -0.1209 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5549 0.2164 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7335 1.2003 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2371 -0.9715 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0605 -0.4872 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0292 1.5096 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.7202 -0.0807 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.9706 1.8469 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.5841 1.7260 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.3118 -0.0807 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8507 0.5257 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.2513 -2.3040 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.4280 -1.7688 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.4095 -1.7343 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0605 -0.4872 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.2664 2.1562 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.5468 1.9966 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.4168 1.4267 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.7807 -2.3040 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5385 0.1706 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 11 1 0 0 0 0 2 12 1 0 0 0 0 5 16 1 0 0 0 0 6 17 1 0 0 0 0 6 18 1 0 0 0 0 7 19 1 0 0 0 0 7 20 1 0 0 0 0 8 21 1 0 0 0 0 8 30 1 0 0 0 0 9 14 1 0 0 0 0 9 33 1 0 0 0 0 10 40 1 0 0 0 0 11 22 2 0 0 0 0 11 25 1 0 0 0 0 12 34 2 0 0 0 0 12 40 1 0 0 0 0 13 5 1 1 0 0 0 13 15 1 0 0 0 0 13 16 1 0 0 0 0 14 18 2 0 0 0 0 14 26 1 0 0 0 0 15 10 1 6 0 0 0 15 17 1 0 0 0 0 16 28 1 1 0 0 0 17 28 1 1 0 0 0 18 31 1 0 0 0 0 19 20 1 0 0 0 0 19 29 1 1 0 0 0 20 30 1 1 0 0 0 21 28 1 6 0 0 0 21 31 1 0 0 0 0 22 23 1 0 0 0 0 22 32 1 0 0 0 0 23 24 2 0 0 0 0 24 29 1 0 0 0 0 24 30 1 0 0 0 0 25 35 2 0 0 0 0 25 42 1 0 0 0 0 26 36 2 0 0 0 0 26 41 1 0 0 0 0 27 29 1 1 0 0 0 27 32 1 0 0 0 0 27 37 1 0 0 0 0 28 3 1 1 0 0 0 29 4 1 1 0 0 0 30 38 1 1 0 0 0 31 23 1 6 0 0 0 31 41 1 0 0 0 0 32 39 1 6 0 0 0 32 42 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	580.23
Volume:	557.103
LogP:	2.896
LogD:	1.926
LogS:	-4.356
# Rotatable Bonds:	4
TPSA:	159.82
# H-Bond Aceptor:	10
# H-Bond Donor:	4
# Rings:	9
# Heavy Atoms:	10

MedChem Properties

QED Drug-Likeness Score:	0.215
Synthetic Accessibility Score:	6.793
Fsp3:	0.719
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.532
MDCK Permeability:	9.47543594520539e-05
Pgp-inhibitor:	0.919
Pgp-substrate:	0.998
Human Intestinal Absorption (HIA):	0.392
20% Bioavailability (F20%):	0.971
30% Bioavailability (F30%):	0.986

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.399
Plasma Protein Binding (PPB):	35.096168518066406%
Volume Distribution (VD):	0.54
Pgp-substrate:	36.28234100341797%

ADMET: Metabolism

CYP1A2-inhibitor:	0.011
CYP1A2-substrate:	0.927
CYP2C19-inhibitor:	0.019
CYP2C19-substrate:	0.629
CYP2C9-inhibitor:	0.009
CYP2C9-substrate:	0.007
CYP2D6-inhibitor:	0.001
CYP2D6-substrate:	0.023
CYP3A4-inhibitor:	0.794
CYP3A4-substrate:	0.57

ADMET: Excretion

Clearance (CL):	2.086
Half-life (T1/2):	0.07

ADMET: Toxicity

hERG Blockers:	0.09
Human Hepatotoxicity (H-HT):	0.135
Drug-inuced Liver Injury (DILI):	0.569
AMES Toxicity:	0.03
Rat Oral Acute Toxicity:	0.18
Maximum Recommended Daily Dose:	0.919
Skin Sensitization:	0.231
Carcinogencity:	0.386
Eye Corrosion:	0.003
Eye Irritation:	0.006
Respiratory Toxicity:	0.984

Download Data

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

Natural Product: NPC226049

Natural Product ID:	NPC226049
*Common Name:**	Chloramultiol E
IUPAC Name:	n.a.
Synonyms:	Chloramultiol E
Standard InCHIKey:	YVBZZMQKQQLIAH-ZQYAKUSDSA-N
Standard InCHI:	InChI=1S/C32H36O10/c1-11-22-23-24-29(4,27(37)32(22,39)42-25(11)35)19-7-20(19)30(24,38)8-21-28(3)16-5-13(16)15(10-40-12(2)34)17(28)6-18-14(9-33)26(36)41-31(18,21)23/h13,15-17,19-21,27,33,37-39H,5-10H2,1-4H3/t13-,15-,16-,17+,19-,20+,21+,27-,28+,29+,30+,31+,32+/m1/s1
SMILES:	OCC1=C2C[C@H]3[C@H](COC(=O)C)[C@@H]4[C@H]([C@@]3([C@H]3[C@]2(OC1=O)C1=C2[C@@](C3)(O)[C@@H]3[C@H]([C@@]2([C@H]([C@@]2(C1=C(C)C(=O)O2)O)O)C)C3)C)C4
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1097990
PubChem CID:	46830520
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
NPO8670	Chloranthus multistachys	Species	Chloranthaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20392109]
NPO8670	Chloranthus multistachys	Species	Chloranthaceae	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

Activity Type	# Activity
IC50	5

Activity Type	# Activity
Cell Line	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	IC50	>	10000.0	nM	PMID[545504]
NPT116	Cell Line	HL-60	Homo sapiens	IC50	>	10000.0	nM	PMID[545504]
NPT461	Cell Line	PANC-1	Homo sapiens	IC50	>	10000.0	nM	PMID[545504]
NPT659	Cell Line	SMMC-7721	Homo sapiens	IC50	>	10000.0	nM	PMID[545504]
NPT134	Cell Line	SK-BR-3	Homo sapiens	IC50	>	10000.0	nM	PMID[545504]

☑ 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 NPC226049 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	302
0.1-0.2	1914
0.2-0.3	5626
0.3-0.4	11882
0.4-0.5	11174
0.5-0.6	7772
0.6-0.7	3576
0.7-0.8	404
0.8-0.85	22
0.85-0.9	9
0.9-0.95	9
0.95-1	7

Similarity Score	Similarity Level	Natural Product ID
0.9912	High Similarity	NPC84865
0.9661	High Similarity	NPC134902
0.958	High Similarity	NPC254823
0.95	High Similarity	NPC476824
0.9421	High Similarity	NPC476097
0.9421	High Similarity	NPC327664
0.9421	High Similarity	NPC470427
0.9344	High Similarity	NPC60150
0.9344	High Similarity	NPC192334
0.9316	High Similarity	NPC27335
0.9262	High Similarity	NPC24599
0.876	High Similarity	NPC25887
0.8682	High Similarity	NPC476825
0.855	High Similarity	NPC470426
0.8359	Intermediate Similarity	NPC469674
0.8217	Intermediate Similarity	NPC469673
0.8203	Intermediate Similarity	NPC220757
0.8203	Intermediate Similarity	NPC196921
0.8203	Intermediate Similarity	NPC279478
0.8203	Intermediate Similarity	NPC241935
0.8154	Intermediate Similarity	NPC476823
0.814	Intermediate Similarity	NPC34963
0.8125	Intermediate Similarity	NPC35109
0.8103	Intermediate Similarity	NPC161775
0.8077	Intermediate Similarity	NPC58029
0.8065	Intermediate Similarity	NPC17938
0.8031	Intermediate Similarity	NPC63186
0.7967	Intermediate Similarity	NPC203862
0.7951	Intermediate Similarity	NPC106446
0.7891	Intermediate Similarity	NPC15095
0.7886	Intermediate Similarity	NPC470075
0.7857	Intermediate Similarity	NPC129434
0.784	Intermediate Similarity	NPC304260
0.784	Intermediate Similarity	NPC5883
0.784	Intermediate Similarity	NPC29639
0.784	Intermediate Similarity	NPC44899
0.7823	Intermediate Similarity	NPC93883
0.7795	Intermediate Similarity	NPC115349
0.7778	Intermediate Similarity	NPC107607
0.7769	Intermediate Similarity	NPC311534
0.776	Intermediate Similarity	NPC218093
0.7742	Intermediate Similarity	NPC99620
0.7742	Intermediate Similarity	NPC5311
0.7742	Intermediate Similarity	NPC193382
0.7742	Intermediate Similarity	NPC310341
0.7742	Intermediate Similarity	NPC199428
0.7719	Intermediate Similarity	NPC329435
0.7717	Intermediate Similarity	NPC40749
0.7717	Intermediate Similarity	NPC475219
0.7717	Intermediate Similarity	NPC231518
0.7712	Intermediate Similarity	NPC85742
0.7698	Intermediate Similarity	NPC292467
0.7698	Intermediate Similarity	NPC291820
0.7698	Intermediate Similarity	NPC236973
0.7698	Intermediate Similarity	NPC232258
0.7698	Intermediate Similarity	NPC30483
0.7698	Intermediate Similarity	NPC81222
0.7698	Intermediate Similarity	NPC32177
0.7698	Intermediate Similarity	NPC469756
0.7698	Intermediate Similarity	NPC153085
0.7698	Intermediate Similarity	NPC268326
0.7698	Intermediate Similarity	NPC55532
0.7698	Intermediate Similarity	NPC470897
0.7686	Intermediate Similarity	NPC257853
0.768	Intermediate Similarity	NPC471355
0.768	Intermediate Similarity	NPC27507
0.768	Intermediate Similarity	NPC158344
0.768	Intermediate Similarity	NPC471353
0.768	Intermediate Similarity	NPC196429
0.768	Intermediate Similarity	NPC471351
0.768	Intermediate Similarity	NPC474418
0.768	Intermediate Similarity	NPC243196
0.768	Intermediate Similarity	NPC77319
0.768	Intermediate Similarity	NPC84987
0.768	Intermediate Similarity	NPC244402
0.768	Intermediate Similarity	NPC34390
0.768	Intermediate Similarity	NPC87250
0.768	Intermediate Similarity	NPC50305
0.768	Intermediate Similarity	NPC471354
0.768	Intermediate Similarity	NPC99728
0.768	Intermediate Similarity	NPC142066
0.768	Intermediate Similarity	NPC309034
0.768	Intermediate Similarity	NPC157376
0.768	Intermediate Similarity	NPC290693
0.768	Intermediate Similarity	NPC473852
0.768	Intermediate Similarity	NPC152615
0.7667	Intermediate Similarity	NPC472820
0.7661	Intermediate Similarity	NPC471633
0.7661	Intermediate Similarity	NPC84949
0.7661	Intermediate Similarity	NPC69576
0.7661	Intermediate Similarity	NPC31354
0.7656	Intermediate Similarity	NPC193893
0.7647	Intermediate Similarity	NPC473543
0.7638	Intermediate Similarity	NPC475556
0.7638	Intermediate Similarity	NPC72260
0.7638	Intermediate Similarity	NPC475629
0.7623	Intermediate Similarity	NPC177047
0.7619	Intermediate Similarity	NPC83287
0.7603	Intermediate Similarity	NPC50124
0.7597	Intermediate Similarity	NPC129992
0.7583	Intermediate Similarity	NPC85670
0.7583	Intermediate Similarity	NPC220217
0.7583	Intermediate Similarity	NPC119855
0.7583	Intermediate Similarity	NPC472818
0.7578	Intermediate Similarity	NPC173555
0.7578	Intermediate Similarity	NPC314535
0.7578	Intermediate Similarity	NPC474908
0.7578	Intermediate Similarity	NPC233500
0.7578	Intermediate Similarity	NPC475419
0.7578	Intermediate Similarity	NPC475590
0.7578	Intermediate Similarity	NPC46570
0.7578	Intermediate Similarity	NPC120390
0.7563	Intermediate Similarity	NPC472821
0.7563	Intermediate Similarity	NPC218513
0.7563	Intermediate Similarity	NPC474822
0.7563	Intermediate Similarity	NPC473523
0.7563	Intermediate Similarity	NPC474124
0.7563	Intermediate Similarity	NPC55954
0.7563	Intermediate Similarity	NPC159533
0.7561	Intermediate Similarity	NPC470076
0.7559	Intermediate Similarity	NPC219656
0.7559	Intermediate Similarity	NPC329905
0.7557	Intermediate Similarity	NPC117702
0.7557	Intermediate Similarity	NPC42399
0.7557	Intermediate Similarity	NPC469757
0.7557	Intermediate Similarity	NPC287423
0.7557	Intermediate Similarity	NPC471357
0.7557	Intermediate Similarity	NPC146456
0.7538	Intermediate Similarity	NPC469790
0.7538	Intermediate Similarity	NPC8374
0.752	Intermediate Similarity	NPC216665
0.752	Intermediate Similarity	NPC43213
0.7519	Intermediate Similarity	NPC474423
0.7519	Intermediate Similarity	NPC107493
0.7519	Intermediate Similarity	NPC470265
0.7519	Intermediate Similarity	NPC471082
0.7519	Intermediate Similarity	NPC269642
0.7519	Intermediate Similarity	NPC173347
0.7519	Intermediate Similarity	NPC74259
0.7519	Intermediate Similarity	NPC196130
0.7519	Intermediate Similarity	NPC23786
0.7519	Intermediate Similarity	NPC264336
0.75	Intermediate Similarity	NPC473577
0.75	Intermediate Similarity	NPC42658
0.75	Intermediate Similarity	NPC328074
0.75	Intermediate Similarity	NPC321272
0.75	Intermediate Similarity	NPC472819
0.75	Intermediate Similarity	NPC474466
0.75	Intermediate Similarity	NPC475585
0.75	Intermediate Similarity	NPC474550
0.75	Intermediate Similarity	NPC475136
0.75	Intermediate Similarity	NPC317460
0.75	Intermediate Similarity	NPC470025
0.75	Intermediate Similarity	NPC200861
0.7481	Intermediate Similarity	NPC471234
0.748	Intermediate Similarity	NPC291564
0.748	Intermediate Similarity	NPC90630
0.748	Intermediate Similarity	NPC475243
0.7479	Intermediate Similarity	NPC475344
0.7479	Intermediate Similarity	NPC470972
0.7479	Intermediate Similarity	NPC472552
0.7479	Intermediate Similarity	NPC471119
0.7479	Intermediate Similarity	NPC476471
0.7479	Intermediate Similarity	NPC296879
0.7463	Intermediate Similarity	NPC231240
0.7462	Intermediate Similarity	NPC219804
0.7462	Intermediate Similarity	NPC27363
0.7462	Intermediate Similarity	NPC308262
0.7462	Intermediate Similarity	NPC208193
0.7462	Intermediate Similarity	NPC117445
0.746	Intermediate Similarity	NPC207637
0.746	Intermediate Similarity	NPC106228
0.746	Intermediate Similarity	NPC212660
0.746	Intermediate Similarity	NPC138372
0.7459	Intermediate Similarity	NPC38948
0.7459	Intermediate Similarity	NPC88701
0.7444	Intermediate Similarity	NPC471359
0.7444	Intermediate Similarity	NPC469753
0.7444	Intermediate Similarity	NPC469754
0.7444	Intermediate Similarity	NPC473593
0.7444	Intermediate Similarity	NPC180079
0.7444	Intermediate Similarity	NPC469755
0.7444	Intermediate Similarity	NPC89514
0.7444	Intermediate Similarity	NPC231529
0.7444	Intermediate Similarity	NPC104382
0.7444	Intermediate Similarity	NPC284406
0.7444	Intermediate Similarity	NPC197707
0.7444	Intermediate Similarity	NPC70542
0.7444	Intermediate Similarity	NPC469751
0.7444	Intermediate Similarity	NPC9499
0.7444	Intermediate Similarity	NPC10823
0.7444	Intermediate Similarity	NPC471352
0.7444	Intermediate Similarity	NPC219085
0.7444	Intermediate Similarity	NPC6108
0.7444	Intermediate Similarity	NPC469752
0.7444	Intermediate Similarity	NPC251866
0.7444	Intermediate Similarity	NPC471358
0.7444	Intermediate Similarity	NPC471360
0.7444	Intermediate Similarity	NPC86159
0.7444	Intermediate Similarity	NPC17896

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 NPC226049 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	259
0.1-0.2	2206
0.2-0.3	4048
0.3-0.4	1813
0.4-0.5	492
0.5-0.6	257
0.6-0.7	73
0.7-0.8	2
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7717	Intermediate Similarity	NPD8033	Approved
0.7638	Intermediate Similarity	NPD8377	Approved
0.7638	Intermediate Similarity	NPD8294	Approved
0.7619	Intermediate Similarity	NPD7328	Approved
0.7619	Intermediate Similarity	NPD7327	Approved
0.7578	Intermediate Similarity	NPD8296	Approved
0.7578	Intermediate Similarity	NPD8380	Approved
0.7578	Intermediate Similarity	NPD8335	Approved
0.7578	Intermediate Similarity	NPD8379	Approved
0.7578	Intermediate Similarity	NPD8378	Approved
0.7559	Intermediate Similarity	NPD7516	Approved
0.7444	Intermediate Similarity	NPD7319	Approved
0.7442	Intermediate Similarity	NPD7503	Approved
0.7348	Intermediate Similarity	NPD7507	Approved
0.7258	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7132	Intermediate Similarity	NPD7115	Discovery
0.7063	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD7078	Approved
0.7025	Intermediate Similarity	NPD7640	Approved
0.7025	Intermediate Similarity	NPD7639	Approved
0.6942	Remote Similarity	NPD7638	Approved
0.6912	Remote Similarity	NPD8293	Discontinued
0.6911	Remote Similarity	NPD7632	Discontinued
0.6889	Remote Similarity	NPD7492	Approved
0.6861	Remote Similarity	NPD7736	Approved
0.6842	Remote Similarity	NPD6059	Approved
0.6842	Remote Similarity	NPD6319	Approved
0.6842	Remote Similarity	NPD6054	Approved
0.6838	Remote Similarity	NPD6616	Approved
0.6825	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6803	Remote Similarity	NPD4225	Approved
0.6772	Remote Similarity	NPD6686	Approved
0.6741	Remote Similarity	NPD6370	Approved
0.6694	Remote Similarity	NPD5344	Discontinued
0.6692	Remote Similarity	NPD6053	Discontinued
0.6692	Remote Similarity	NPD8297	Approved
0.6667	Remote Similarity	NPD8513	Phase 3
0.6667	Remote Similarity	NPD6371	Approved
0.6667	Remote Similarity	NPD8517	Approved
0.6667	Remote Similarity	NPD6015	Approved
0.6667	Remote Similarity	NPD8515	Approved
0.6667	Remote Similarity	NPD6016	Approved
0.6667	Remote Similarity	NPD8516	Approved
0.6641	Remote Similarity	NPD8133	Approved
0.6641	Remote Similarity	NPD7320	Approved
0.6618	Remote Similarity	NPD5988	Approved
0.6613	Remote Similarity	NPD6648	Approved
0.6589	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6565	Remote Similarity	NPD6882	Approved
0.6562	Remote Similarity	NPD6412	Phase 2
0.6515	Remote Similarity	NPD4632	Approved
0.65	Remote Similarity	NPD7838	Discovery
0.6493	Remote Similarity	NPD6009	Approved
0.6493	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6484	Remote Similarity	NPD6402	Approved
0.6484	Remote Similarity	NPD7128	Approved
0.6484	Remote Similarity	NPD5739	Approved
0.6484	Remote Similarity	NPD6008	Approved
0.6484	Remote Similarity	NPD6675	Approved
0.6462	Remote Similarity	NPD6372	Approved
0.6462	Remote Similarity	NPD6373	Approved
0.6449	Remote Similarity	NPD7604	Phase 2
0.6446	Remote Similarity	NPD7637	Suspended
0.6434	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD8074	Phase 3
0.6424	Remote Similarity	NPD7625	Phase 1
0.64	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6385	Remote Similarity	NPD6899	Approved
0.6385	Remote Similarity	NPD6881	Approved
0.6383	Remote Similarity	NPD6033	Approved
0.6364	Remote Similarity	NPD6650	Approved
0.6364	Remote Similarity	NPD6649	Approved
0.6364	Remote Similarity	NPD8130	Phase 1
0.6331	Remote Similarity	NPD8328	Phase 3
0.6308	Remote Similarity	NPD5701	Approved
0.6308	Remote Similarity	NPD5697	Approved
0.6299	Remote Similarity	NPD4159	Approved
0.6288	Remote Similarity	NPD6883	Approved
0.6288	Remote Similarity	NPD7290	Approved
0.6288	Remote Similarity	NPD4634	Approved
0.6288	Remote Similarity	NPD7102	Approved
0.625	Remote Similarity	NPD7524	Approved
0.6241	Remote Similarity	NPD6847	Approved
0.6241	Remote Similarity	NPD6869	Approved
0.6241	Remote Similarity	NPD6617	Approved
0.6212	Remote Similarity	NPD6013	Approved
0.6212	Remote Similarity	NPD6014	Approved
0.6212	Remote Similarity	NPD6012	Approved
0.619	Remote Similarity	NPD6084	Phase 2
0.619	Remote Similarity	NPD6083	Phase 2
0.6187	Remote Similarity	NPD5983	Phase 2
0.616	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.616	Remote Similarity	NPD5695	Phase 3
0.6148	Remote Similarity	NPD6051	Approved
0.6136	Remote Similarity	NPD6011	Approved
0.6136	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6134	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6129	Remote Similarity	NPD5778	Approved
0.6129	Remote Similarity	NPD5779	Approved
0.6127	Remote Similarity	NPD6336	Discontinued
0.6124	Remote Similarity	NPD5211	Phase 2
0.6119	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6099	Remote Similarity	NPD6067	Discontinued
0.6098	Remote Similarity	NPD46	Approved
0.6098	Remote Similarity	NPD6698	Approved
0.6096	Remote Similarity	NPD6845	Suspended
0.608	Remote Similarity	NPD6001	Approved
0.6063	Remote Similarity	NPD4755	Approved
0.605	Remote Similarity	NPD6695	Phase 3
0.6048	Remote Similarity	NPD5284	Approved
0.6048	Remote Similarity	NPD7983	Approved
0.6048	Remote Similarity	NPD5281	Approved
0.6036	Remote Similarity	NPD7799	Discontinued
0.6031	Remote Similarity	NPD5141	Approved
0.6027	Remote Similarity	NPD7260	Phase 2
0.6	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6	Remote Similarity	NPD4202	Approved
0.6	Remote Similarity	NPD8171	Discontinued
0.6	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6	Remote Similarity	NPD6399	Phase 3
0.5984	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.5984	Remote Similarity	NPD7750	Discontinued
0.5969	Remote Similarity	NPD4700	Approved
0.5969	Remote Similarity	NPD4696	Approved
0.5969	Remote Similarity	NPD5286	Approved
0.5969	Remote Similarity	NPD5285	Approved
0.5959	Remote Similarity	NPD5956	Approved
0.5942	Remote Similarity	NPD6274	Approved
0.5935	Remote Similarity	NPD6903	Approved
0.5932	Remote Similarity	NPD4748	Discontinued
0.5929	Remote Similarity	NPD7100	Approved
0.5929	Remote Similarity	NPD7101	Approved
0.592	Remote Similarity	NPD6050	Approved
0.592	Remote Similarity	NPD6411	Approved
0.5909	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.5891	Remote Similarity	NPD5696	Approved
0.5878	Remote Similarity	NPD5225	Approved
0.5878	Remote Similarity	NPD4633	Approved
0.5878	Remote Similarity	NPD5226	Approved
0.5878	Remote Similarity	NPD5224	Approved
0.5865	Remote Similarity	NPD4768	Approved
0.5865	Remote Similarity	NPD4767	Approved
0.5857	Remote Similarity	NPD6335	Approved
0.5845	Remote Similarity	NPD6909	Approved
0.5845	Remote Similarity	NPD6908	Approved
0.584	Remote Similarity	NPD5207	Approved
0.584	Remote Similarity	NPD5692	Phase 3
0.584	Remote Similarity	NPD5785	Approved
0.5833	Remote Similarity	NPD5174	Approved
0.5833	Remote Similarity	NPD5175	Approved
0.5827	Remote Similarity	NPD7748	Approved
0.582	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.5814	Remote Similarity	NPD5959	Approved
0.5814	Remote Similarity	NPD7902	Approved
0.5802	Remote Similarity	NPD5223	Approved
0.5802	Remote Similarity	NPD1700	Approved
0.5798	Remote Similarity	NPD6930	Phase 2
0.5798	Remote Similarity	NPD7525	Registered
0.5798	Remote Similarity	NPD6931	Approved
0.5794	Remote Similarity	NPD5694	Approved
0.5794	Remote Similarity	NPD8034	Phase 2
0.5794	Remote Similarity	NPD8035	Phase 2
0.5794	Remote Similarity	NPD5693	Phase 1
0.5786	Remote Similarity	NPD6317	Approved
0.5778	Remote Similarity	NPD4730	Approved
0.5778	Remote Similarity	NPD4729	Approved
0.5772	Remote Similarity	NPD7521	Approved
0.5772	Remote Similarity	NPD6684	Approved
0.5772	Remote Similarity	NPD7334	Approved
0.5772	Remote Similarity	NPD7146	Approved
0.5772	Remote Similarity	NPD5330	Approved
0.5772	Remote Similarity	NPD6409	Approved
0.576	Remote Similarity	NPD5328	Approved
0.576	Remote Similarity	NPD4753	Phase 2
0.576	Remote Similarity	NPD6101	Approved
0.576	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.575	Remote Similarity	NPD6902	Approved
0.5745	Remote Similarity	NPD6313	Approved
0.5745	Remote Similarity	NPD6314	Approved
0.5734	Remote Similarity	NPD6921	Approved
0.5734	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.5726	Remote Similarity	NPD4251	Approved
0.5726	Remote Similarity	NPD4250	Approved
0.5714	Remote Similarity	NPD4754	Approved
0.5714	Remote Similarity	NPD6929	Approved
0.5693	Remote Similarity	NPD5247	Approved
0.5693	Remote Similarity	NPD5248	Approved
0.5693	Remote Similarity	NPD5250	Approved
0.5693	Remote Similarity	NPD5249	Phase 3
0.5693	Remote Similarity	NPD5251	Approved
0.5686	Remote Similarity	NPD6334	Approved
0.5686	Remote Similarity	NPD6333	Approved
0.568	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.5669	Remote Similarity	NPD7087	Discontinued
0.5669	Remote Similarity	NPD6079	Approved
0.5669	Remote Similarity	NPD7515	Phase 2
0.5667	Remote Similarity	NPD6928	Phase 2
0.5667	Remote Similarity	NPD8449	Approved
0.5667	Remote Similarity	NPD7514	Phase 3
0.5662	Remote Similarity	NPD5128	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