NPASS Compound

Structure

NPC38948 OpenBabel07101718322D 31 34 0 0 1 0 0 0 0 0999 V2000 -5.2812 2.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.0007 2.6939 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5689 2.4684 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8289 2.1775 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1831 -0.5570 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7888 2.8528 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4152 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5491 1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5543 2.5785 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0971 2.4253 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1472 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.4619 0.9726 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8171 -0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2812 1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.7928 1.7158 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.0132 1.8090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.9511 0.3090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.6831 1.3090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -8.9619 0.1066 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.8793 1.3090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.9511 1.3090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.5878 0.8090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.8171 1.8090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 1.6180 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.6831 0.3090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.0132 2.8090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.3687 -0.8070 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5878 0.8090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.6831 0.3090 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 -7.9838 0.3145 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 14 1 0 0 0 0 2 15 1 0 0 0 0 6 9 1 0 0 0 0 6 10 1 0 0 0 0 7 8 1 0 0 0 0 7 14 1 0 0 0 0 8 18 1 0 0 0 0 9 23 1 0 0 0 0 10 24 1 0 0 0 0 11 14 2 0 0 0 0 11 16 1 0 0 0 0 12 15 2 0 0 0 0 12 19 1 0 0 0 0 13 25 1 0 0 0 0 15 20 1 0 0 0 0 16 26 1 1 0 0 0 17 13 1 1 0 0 0 17 21 1 0 0 0 0 17 30 1 0 0 0 0 18 23 1 6 0 0 0 18 25 1 0 0 0 0 19 27 2 0 0 0 0 19 31 1 0 0 0 0 20 16 1 1 0 0 0 20 31 1 0 0 0 0 21 23 1 6 0 0 0 21 24 1 0 0 0 0 22 24 1 1 0 0 0 22 28 1 0 0 0 0 22 30 1 0 0 0 0 23 3 1 6 0 0 0 24 4 1 6 0 0 0 25 5 1 6 0 0 0 25 29 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	434.27
Volume:	451.562
LogP:	3.445
LogD:	3.464
LogS:	-4.121
# Rotatable Bonds:	5
TPSA:	103.29
# H-Bond Aceptor:	6
# H-Bond Donor:	4
# Rings:	4
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.514
Synthetic Accessibility Score:	5.436
Fsp3:	0.76
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-5.031
MDCK Permeability:	1.5933163012959994e-05
Pgp-inhibitor:	0.07
Pgp-substrate:	0.998
Human Intestinal Absorption (HIA):	0.347
20% Bioavailability (F20%):	0.413
30% Bioavailability (F30%):	0.807

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.691
Plasma Protein Binding (PPB):	93.2706069946289%
Volume Distribution (VD):	1.453
Pgp-substrate:	8.295681953430176%

ADMET: Metabolism

CYP1A2-inhibitor:	0.01
CYP1A2-substrate:	0.853
CYP2C19-inhibitor:	0.023
CYP2C19-substrate:	0.787
CYP2C9-inhibitor:	0.153
CYP2C9-substrate:	0.178
CYP2D6-inhibitor:	0.02
CYP2D6-substrate:	0.188
CYP3A4-inhibitor:	0.691
CYP3A4-substrate:	0.307

ADMET: Excretion

Clearance (CL):	6.507
Half-life (T1/2):	0.757

ADMET: Toxicity

hERG Blockers:	0.038
Human Hepatotoxicity (H-HT):	0.535
Drug-inuced Liver Injury (DILI):	0.232
AMES Toxicity:	0.542
Rat Oral Acute Toxicity:	0.78
Maximum Recommended Daily Dose:	0.947
Skin Sensitization:	0.247
Carcinogencity:	0.062
Eye Corrosion:	0.003
Eye Irritation:	0.019
Respiratory Toxicity:	0.973

Download Data

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

Natural Product: NPC38948

Natural Product ID:	NPC38948
*Common Name:**	DOMUYBKPZYQPSE-FXTKAKNUSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	DOMUYBKPZYQPSE-FXTKAKNUSA-N
Standard InCHI:	InChI=1S/C25H38O6/c1-14(11-16(26)20-15(2)12-19(27)31-20)7-8-18-23(3)9-6-10-24(4)21(23)17(30-22(24)28)13-25(18,5)29/h11-12,16-18,20-22,26,28-29H,6-10,13H2,1-5H3/b14-11+/t16-,17-,18+,20-,21+,22-,23+,24+,25+/m0/s1
SMILES:	C/C(=C[C@@H]([C@H]1OC(=O)C=C1C)O)/CC[C@H]1[C@](C)(O)C[C@H]2[C@@H]3[C@]1(C)CCC[C@@]3(C)[C@H](O2)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL484898
PubChem CID:	44157603
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001552] Sesterterpenoids

*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
NPO33075	salvia dominica	Species	Lamiaceae	Eukaryota	aerial parts	n.a.	n.a.	PMID[19459643]

☑ 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
Kd	1

Activity Type	# Activity
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT6478	Individual Protein	Tubulin--tyrosine ligase	Homo sapiens	Kd	=	210000.0	nM	PMID[509495]

☑ 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 NPC38948 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	196
0.1-0.2	1343
0.2-0.3	4260
0.3-0.4	7551
0.4-0.5	12802
0.5-0.6	7349
0.6-0.7	6155
0.7-0.8	2581
0.8-0.85	381
0.85-0.9	69
0.9-0.95	5
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
0.99	High Similarity	NPC206618
0.9495	High Similarity	NPC472815
0.94	High Similarity	NPC120009
0.9293	High Similarity	NPC38855
0.9126	High Similarity	NPC475074
0.91	High Similarity	NPC324841
0.8942	High Similarity	NPC471205
0.8889	High Similarity	NPC276110
0.8868	High Similarity	NPC177047
0.8846	High Similarity	NPC239961
0.8824	High Similarity	NPC472554
0.8762	High Similarity	NPC187435
0.8762	High Similarity	NPC67321
0.8762	High Similarity	NPC122816
0.8738	High Similarity	NPC472552
0.8727	High Similarity	NPC157376
0.8727	High Similarity	NPC99728
0.8727	High Similarity	NPC50305
0.8727	High Similarity	NPC473852
0.8727	High Similarity	NPC474418
0.8727	High Similarity	NPC471351
0.8727	High Similarity	NPC243196
0.8727	High Similarity	NPC203862
0.8727	High Similarity	NPC27507
0.8727	High Similarity	NPC84987
0.8727	High Similarity	NPC471354
0.8727	High Similarity	NPC142066
0.8727	High Similarity	NPC34390
0.8727	High Similarity	NPC196429
0.8727	High Similarity	NPC77319
0.8727	High Similarity	NPC158344
0.8727	High Similarity	NPC471355
0.8727	High Similarity	NPC87250
0.8727	High Similarity	NPC471353
0.8727	High Similarity	NPC309034
0.8727	High Similarity	NPC244402
0.8716	High Similarity	NPC84949
0.8716	High Similarity	NPC69576
0.8716	High Similarity	NPC31354
0.8716	High Similarity	NPC471633
0.8704	High Similarity	NPC328074
0.8704	High Similarity	NPC317460
0.8704	High Similarity	NPC470025
0.8704	High Similarity	NPC321272
0.8687	High Similarity	NPC472812
0.8687	High Similarity	NPC53555
0.8679	High Similarity	NPC181994
0.8667	High Similarity	NPC51719
0.8654	High Similarity	NPC45897
0.8654	High Similarity	NPC281378
0.8649	High Similarity	NPC83287
0.8641	High Similarity	NPC11974
0.8636	High Similarity	NPC471816
0.8636	High Similarity	NPC5311
0.8636	High Similarity	NPC199428
0.8636	High Similarity	NPC310341
0.8636	High Similarity	NPC99620
0.8636	High Similarity	NPC193382
0.8624	High Similarity	NPC264153
0.8624	High Similarity	NPC470027
0.8614	High Similarity	NPC165632
0.8611	High Similarity	NPC17791
0.86	High Similarity	NPC105490
0.8586	High Similarity	NPC472811
0.8571	High Similarity	NPC153085
0.8571	High Similarity	NPC29639
0.8571	High Similarity	NPC44899
0.8571	High Similarity	NPC304260
0.8571	High Similarity	NPC5883
0.8571	High Similarity	NPC268326
0.8559	High Similarity	NPC152615
0.8559	High Similarity	NPC290693
0.8559	High Similarity	NPC93883
0.8558	High Similarity	NPC121423
0.8558	High Similarity	NPC11956
0.8544	High Similarity	NPC477968
0.8544	High Similarity	NPC477972
0.8544	High Similarity	NPC477971
0.8544	High Similarity	NPC219285
0.8544	High Similarity	NPC161527
0.8544	High Similarity	NPC228251
0.8544	High Similarity	NPC16601
0.8544	High Similarity	NPC20113
0.8519	High Similarity	NPC316708
0.8515	High Similarity	NPC472441
0.8505	High Similarity	NPC470024
0.8505	High Similarity	NPC217921
0.8505	High Similarity	NPC50124
0.8505	High Similarity	NPC128795
0.8505	High Similarity	NPC306265
0.8505	High Similarity	NPC135015
0.8505	High Similarity	NPC48548
0.85	High Similarity	NPC472640
0.85	High Similarity	NPC472641
0.85	High Similarity	NPC7349
0.8496	Intermediate Similarity	NPC475136
0.8496	Intermediate Similarity	NPC474466
0.8496	Intermediate Similarity	NPC475629
0.8496	Intermediate Similarity	NPC475556
0.8491	Intermediate Similarity	NPC470056
0.8491	Intermediate Similarity	NPC218158
0.8491	Intermediate Similarity	NPC470055
0.8485	Intermediate Similarity	NPC78973
0.8482	Intermediate Similarity	NPC218093
0.8476	Intermediate Similarity	NPC23584
0.8476	Intermediate Similarity	NPC471938
0.8462	Intermediate Similarity	NPC198992
0.8447	Intermediate Similarity	NPC275086
0.8447	Intermediate Similarity	NPC325229
0.8447	Intermediate Similarity	NPC278673
0.844	Intermediate Similarity	NPC470026
0.8426	Intermediate Similarity	NPC316974
0.8426	Intermediate Similarity	NPC40728
0.8421	Intermediate Similarity	NPC173555
0.8421	Intermediate Similarity	NPC40749
0.8421	Intermediate Similarity	NPC231518
0.8421	Intermediate Similarity	NPC314535
0.8421	Intermediate Similarity	NPC475219
0.8416	Intermediate Similarity	NPC469697
0.8411	Intermediate Similarity	NPC472390
0.8411	Intermediate Similarity	NPC88013
0.8411	Intermediate Similarity	NPC109376
0.8411	Intermediate Similarity	NPC125423
0.8411	Intermediate Similarity	NPC472820
0.8407	Intermediate Similarity	NPC291820
0.8407	Intermediate Similarity	NPC292467
0.8407	Intermediate Similarity	NPC55532
0.8407	Intermediate Similarity	NPC30483
0.8407	Intermediate Similarity	NPC81222
0.8407	Intermediate Similarity	NPC32177
0.8407	Intermediate Similarity	NPC469756
0.8407	Intermediate Similarity	NPC329905
0.8407	Intermediate Similarity	NPC236973
0.8407	Intermediate Similarity	NPC470897
0.8396	Intermediate Similarity	NPC470064
0.8396	Intermediate Similarity	NPC470058
0.8396	Intermediate Similarity	NPC470062
0.8396	Intermediate Similarity	NPC470057
0.8396	Intermediate Similarity	NPC470060
0.8396	Intermediate Similarity	NPC470043
0.8396	Intermediate Similarity	NPC470059
0.8396	Intermediate Similarity	NPC85593
0.8396	Intermediate Similarity	NPC470061
0.8396	Intermediate Similarity	NPC471937
0.8396	Intermediate Similarity	NPC31430
0.8393	Intermediate Similarity	NPC13713
0.8381	Intermediate Similarity	NPC109195
0.8381	Intermediate Similarity	NPC476081
0.8381	Intermediate Similarity	NPC471363
0.8381	Intermediate Similarity	NPC470571
0.8381	Intermediate Similarity	NPC471914
0.8381	Intermediate Similarity	NPC475038
0.8381	Intermediate Similarity	NPC238397
0.8365	Intermediate Similarity	NPC477716
0.8365	Intermediate Similarity	NPC477721
0.835	Intermediate Similarity	NPC51499
0.835	Intermediate Similarity	NPC477719
0.835	Intermediate Similarity	NPC477718
0.835	Intermediate Similarity	NPC473244
0.8349	Intermediate Similarity	NPC235014
0.8348	Intermediate Similarity	NPC471082
0.8348	Intermediate Similarity	NPC115349
0.8348	Intermediate Similarity	NPC193893
0.8348	Intermediate Similarity	NPC264336
0.8333	Intermediate Similarity	NPC224660
0.8333	Intermediate Similarity	NPC107607
0.8333	Intermediate Similarity	NPC72260
0.8333	Intermediate Similarity	NPC311223
0.8333	Intermediate Similarity	NPC471915
0.8318	Intermediate Similarity	NPC172867
0.8318	Intermediate Similarity	NPC119855
0.8318	Intermediate Similarity	NPC472818
0.8318	Intermediate Similarity	NPC220217
0.8318	Intermediate Similarity	NPC471206
0.8317	Intermediate Similarity	NPC110022
0.8304	Intermediate Similarity	NPC207637
0.8302	Intermediate Similarity	NPC189588
0.8302	Intermediate Similarity	NPC10232
0.8302	Intermediate Similarity	NPC474575
0.8302	Intermediate Similarity	NPC196471
0.8302	Intermediate Similarity	NPC97487
0.8302	Intermediate Similarity	NPC474822
0.8302	Intermediate Similarity	NPC7613
0.8302	Intermediate Similarity	NPC127933
0.8302	Intermediate Similarity	NPC7644
0.8302	Intermediate Similarity	NPC187302
0.8302	Intermediate Similarity	NPC134270
0.8302	Intermediate Similarity	NPC472821
0.8302	Intermediate Similarity	NPC475889
0.83	Intermediate Similarity	NPC472642
0.8286	Intermediate Similarity	NPC477717
0.8286	Intermediate Similarity	NPC475617
0.8283	Intermediate Similarity	NPC472810
0.8283	Intermediate Similarity	NPC472809
0.8283	Intermediate Similarity	NPC474629
0.8276	Intermediate Similarity	NPC308262
0.8276	Intermediate Similarity	NPC117445
0.8276	Intermediate Similarity	NPC469382
0.8276	Intermediate Similarity	NPC208193
0.8269	Intermediate Similarity	NPC473154

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 NPC38948 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	162
0.1-0.2	1523
0.2-0.3	3841
0.3-0.4	2369
0.4-0.5	760
0.5-0.6	278
0.6-0.7	183
0.7-0.8	22
0.8-0.85	11
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8649	High Similarity	NPD7328	Approved
0.8649	High Similarity	NPD7327	Approved
0.8571	High Similarity	NPD7516	Approved
0.8421	Intermediate Similarity	NPD8296	Approved
0.8421	Intermediate Similarity	NPD8033	Approved
0.8421	Intermediate Similarity	NPD8378	Approved
0.8421	Intermediate Similarity	NPD8335	Approved
0.8421	Intermediate Similarity	NPD8380	Approved
0.8421	Intermediate Similarity	NPD8379	Approved
0.8333	Intermediate Similarity	NPD8377	Approved
0.8333	Intermediate Similarity	NPD8294	Approved
0.8165	Intermediate Similarity	NPD6686	Approved
0.8095	Intermediate Similarity	NPD4225	Approved
0.7983	Intermediate Similarity	NPD7507	Approved
0.7944	Intermediate Similarity	NPD5344	Discontinued
0.7934	Intermediate Similarity	NPD7319	Approved
0.785	Intermediate Similarity	NPD7640	Approved
0.785	Intermediate Similarity	NPD7639	Approved
0.7797	Intermediate Similarity	NPD7503	Approved
0.7768	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7757	Intermediate Similarity	NPD7638	Approved
0.7525	Intermediate Similarity	NPD6400	Clinical (unspecified phase)
0.7523	Intermediate Similarity	NPD6648	Approved
0.7391	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7311	Intermediate Similarity	NPD7115	Discovery
0.7281	Intermediate Similarity	NPD6412	Phase 2
0.7232	Intermediate Similarity	NPD7632	Discontinued
0.7203	Intermediate Similarity	NPD8133	Approved
0.72	Intermediate Similarity	NPD8293	Discontinued
0.7154	Intermediate Similarity	NPD6370	Approved
0.7143	Intermediate Similarity	NPD7524	Approved
0.7143	Intermediate Similarity	NPD7736	Approved
0.713	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD8516	Approved
0.7073	Intermediate Similarity	NPD8515	Approved
0.7073	Intermediate Similarity	NPD8513	Phase 3
0.7073	Intermediate Similarity	NPD8517	Approved
0.704	Intermediate Similarity	NPD7492	Approved
0.7019	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.7009	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.6992	Remote Similarity	NPD6054	Approved
0.6992	Remote Similarity	NPD6059	Approved
0.6984	Remote Similarity	NPD6616	Approved
0.6964	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.696	Remote Similarity	NPD8328	Phase 3
0.6944	Remote Similarity	NPD7838	Discovery
0.6944	Remote Similarity	NPD6698	Approved
0.6944	Remote Similarity	NPD46	Approved
0.6929	Remote Similarity	NPD7078	Approved
0.6923	Remote Similarity	NPD6695	Phase 3
0.6923	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6881	Remote Similarity	NPD7637	Suspended
0.6825	Remote Similarity	NPD6067	Discontinued
0.6807	Remote Similarity	NPD6371	Approved
0.68	Remote Similarity	NPD6016	Approved
0.68	Remote Similarity	NPD6015	Approved
0.678	Remote Similarity	NPD7320	Approved
0.6777	Remote Similarity	NPD4632	Approved
0.6763	Remote Similarity	NPD7625	Phase 1
0.6752	Remote Similarity	NPD6008	Approved
0.6752	Remote Similarity	NPD6675	Approved
0.6752	Remote Similarity	NPD7128	Approved
0.6752	Remote Similarity	NPD6402	Approved
0.6752	Remote Similarity	NPD5739	Approved
0.675	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6748	Remote Similarity	NPD6009	Approved
0.6748	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6746	Remote Similarity	NPD5988	Approved
0.672	Remote Similarity	NPD6319	Approved
0.6695	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6694	Remote Similarity	NPD8297	Approved
0.6694	Remote Similarity	NPD6882	Approved
0.6694	Remote Similarity	NPD6053	Discontinued
0.6667	Remote Similarity	NPD7750	Discontinued
0.6667	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6639	Remote Similarity	NPD6881	Approved
0.6639	Remote Similarity	NPD6899	Approved
0.6635	Remote Similarity	NPD6930	Phase 2
0.6635	Remote Similarity	NPD6931	Approved
0.6635	Remote Similarity	NPD7525	Registered
0.6607	Remote Similarity	NPD7748	Approved
0.6583	Remote Similarity	NPD6372	Approved
0.6583	Remote Similarity	NPD6373	Approved
0.6579	Remote Similarity	NPD7902	Approved
0.6577	Remote Similarity	NPD7515	Phase 2
0.6555	Remote Similarity	NPD5697	Approved
0.6555	Remote Similarity	NPD5701	Approved
0.6545	Remote Similarity	NPD6051	Approved
0.6538	Remote Similarity	NPD6929	Approved
0.6538	Remote Similarity	NPD8074	Phase 3
0.6529	Remote Similarity	NPD7290	Approved
0.6529	Remote Similarity	NPD7102	Approved
0.6529	Remote Similarity	NPD6883	Approved
0.6518	Remote Similarity	NPD6399	Phase 3
0.6489	Remote Similarity	NPD6033	Approved
0.6486	Remote Similarity	NPD3168	Discontinued
0.6476	Remote Similarity	NPD7514	Phase 3
0.6476	Remote Similarity	NPD7332	Phase 2
0.6475	Remote Similarity	NPD6650	Approved
0.6475	Remote Similarity	NPD6847	Approved
0.6475	Remote Similarity	NPD6649	Approved
0.6475	Remote Similarity	NPD6869	Approved
0.6475	Remote Similarity	NPD6617	Approved
0.6475	Remote Similarity	NPD8130	Phase 1
0.6446	Remote Similarity	NPD6014	Approved
0.6446	Remote Similarity	NPD6013	Approved
0.6446	Remote Similarity	NPD6012	Approved
0.6435	Remote Similarity	NPD6084	Phase 2
0.6435	Remote Similarity	NPD6083	Phase 2
0.6434	Remote Similarity	NPD7604	Phase 2
0.6429	Remote Similarity	NPD7087	Discontinued
0.641	Remote Similarity	NPD4159	Approved
0.6406	Remote Similarity	NPD5983	Phase 2
0.6381	Remote Similarity	NPD7645	Phase 2
0.6372	Remote Similarity	NPD5778	Approved
0.6372	Remote Similarity	NPD5779	Approved
0.6364	Remote Similarity	NPD4250	Approved
0.6364	Remote Similarity	NPD7274	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD4251	Approved
0.6364	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD6011	Approved
0.6356	Remote Similarity	NPD5211	Phase 2
0.6346	Remote Similarity	NPD6925	Approved
0.6346	Remote Similarity	NPD5776	Phase 2
0.6341	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6336	Remote Similarity	NPD6336	Discontinued
0.6333	Remote Similarity	NPD6640	Phase 3
0.633	Remote Similarity	NPD6893	Approved
0.633	Remote Similarity	NPD1694	Approved
0.6316	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD7900	Approved
0.6293	Remote Similarity	NPD4755	Approved
0.6286	Remote Similarity	NPD7145	Approved
0.6283	Remote Similarity	NPD7983	Approved
0.6279	Remote Similarity	NPD6921	Approved
0.6273	Remote Similarity	NPD3618	Phase 1
0.6273	Remote Similarity	NPD4249	Approved
0.6262	Remote Similarity	NPD6898	Phase 1
0.6262	Remote Similarity	NPD6902	Approved
0.6261	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6261	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.626	Remote Similarity	NPD4634	Approved
0.625	Remote Similarity	NPD5328	Approved
0.625	Remote Similarity	NPD5141	Approved
0.625	Remote Similarity	NPD6933	Approved
0.6228	Remote Similarity	NPD4202	Approved
0.6228	Remote Similarity	NPD8171	Discontinued
0.619	Remote Similarity	NPD6932	Approved
0.6186	Remote Similarity	NPD4700	Approved
0.6186	Remote Similarity	NPD5286	Approved
0.6186	Remote Similarity	NPD5285	Approved
0.6186	Remote Similarity	NPD4696	Approved
0.6174	Remote Similarity	NPD5282	Discontinued
0.6161	Remote Similarity	NPD6903	Approved
0.6154	Remote Similarity	NPD6942	Approved
0.6154	Remote Similarity	NPD7339	Approved
0.6142	Remote Similarity	NPD6274	Approved
0.614	Remote Similarity	NPD6079	Approved
0.614	Remote Similarity	NPD8034	Phase 2
0.614	Remote Similarity	NPD8035	Phase 2
0.6126	Remote Similarity	NPD6684	Approved
0.6126	Remote Similarity	NPD5330	Approved
0.6126	Remote Similarity	NPD7146	Approved
0.6126	Remote Similarity	NPD7521	Approved
0.6126	Remote Similarity	NPD7334	Approved
0.6126	Remote Similarity	NPD6409	Approved
0.6124	Remote Similarity	NPD7100	Approved
0.6124	Remote Similarity	NPD7101	Approved
0.6121	Remote Similarity	NPD5695	Phase 3
0.6102	Remote Similarity	NPD5696	Approved
0.6095	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6091	Remote Similarity	NPD4786	Approved
0.6083	Remote Similarity	NPD5224	Approved
0.6083	Remote Similarity	NPD4633	Approved
0.6083	Remote Similarity	NPD5226	Approved
0.6083	Remote Similarity	NPD5225	Approved
0.6075	Remote Similarity	NPD6683	Phase 2
0.6068	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.6066	Remote Similarity	NPD5357	Phase 1
0.6058	Remote Similarity	NPD6926	Approved
0.6058	Remote Similarity	NPD6924	Approved
0.6058	Remote Similarity	NPD8449	Approved
0.6055	Remote Similarity	NPD3667	Approved
0.6053	Remote Similarity	NPD5785	Approved
0.6047	Remote Similarity	NPD6335	Approved
0.6036	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6036	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6033	Remote Similarity	NPD5174	Approved
0.6033	Remote Similarity	NPD5175	Approved
0.6031	Remote Similarity	NPD6908	Approved
0.6031	Remote Similarity	NPD6909	Approved
0.6031	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6029	Remote Similarity	NPD5956	Approved
0.6019	Remote Similarity	NPD4820	Approved
0.6019	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6019	Remote Similarity	NPD4822	Approved
0.6019	Remote Similarity	NPD7509	Discontinued
0.6019	Remote Similarity	NPD4819	Approved
0.6019	Remote Similarity	NPD4821	Approved
0.6018	Remote Similarity	NPD7513	Clinical (unspecified phase)

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