NPASS Compound

Structure

NPC157739 OpenBabel07101718202D 39 43 0 0 1 0 0 0 0 0999 V2000 -9.1664 4.4680 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.5215 3.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.1883 4.2601 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.4670 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.8793 1.6910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.4641 4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.8793 3.3090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.3301 0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5981 0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.0622 1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.9282 2.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.1962 2.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 2.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.9282 3.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.3301 1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.3301 4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 3.0000 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 1.7321 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 6 2 0 0 0 0 3 18 1 0 0 0 0 4 19 1 0 0 0 0 6 20 1 0 0 0 0 7 9 1 0 0 0 0 7 21 1 0 0 0 0 8 10 1 0 0 0 0 8 20 1 0 0 0 0 10 24 1 0 0 0 0 11 14 1 0 0 0 0 11 22 1 0 0 0 0 12 13 1 0 0 0 0 12 25 1 0 0 0 0 13 30 1 0 0 0 0 14 31 1 0 0 0 0 15 21 1 0 0 0 0 15 22 1 0 0 0 0 16 36 1 0 0 0 0 17 2 1 6 0 0 0 17 28 1 0 0 0 0 17 37 1 0 0 0 0 18 32 2 0 0 0 0 18 36 1 0 0 0 0 19 33 2 0 0 0 0 19 38 1 0 0 0 0 20 30 1 6 0 0 0 21 31 1 6 0 0 0 22 39 1 6 0 0 0 23 9 1 1 0 0 0 23 24 1 0 0 0 0 23 25 1 0 0 0 0 24 30 1 6 0 0 0 25 31 1 6 0 0 0 26 27 1 0 0 0 0 26 28 1 0 0 0 0 26 34 1 6 0 0 0 27 29 1 0 0 0 0 27 35 1 1 0 0 0 28 38 1 6 0 0 0 29 37 1 0 0 0 0 29 39 1 1 0 0 0 30 5 1 6 0 0 0 31 16 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	548.33
Volume:	564.362
LogP:	4.471
LogD:	4.268
LogS:	-4.349
# Rotatable Bonds:	8
TPSA:	111.52
# H-Bond Aceptor:	8
# H-Bond Donor:	2
# Rings:	5
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.289
Synthetic Accessibility Score:	5.114
Fsp3:	0.871
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:	-4.854
MDCK Permeability:	3.889777872245759e-05
Pgp-inhibitor:	0.995
Pgp-substrate:	0.965
Human Intestinal Absorption (HIA):	0.113
20% Bioavailability (F20%):	0.007
30% Bioavailability (F30%):	0.029

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.092
Plasma Protein Binding (PPB):	81.8506088256836%
Volume Distribution (VD):	1.307
Pgp-substrate:	9.019100189208984%

ADMET: Metabolism

CYP1A2-inhibitor:	0.029
CYP1A2-substrate:	0.12
CYP2C19-inhibitor:	0.024
CYP2C19-substrate:	0.447
CYP2C9-inhibitor:	0.057
CYP2C9-substrate:	0.027
CYP2D6-inhibitor:	0.016
CYP2D6-substrate:	0.087
CYP3A4-inhibitor:	0.85
CYP3A4-substrate:	0.3

ADMET: Excretion

Clearance (CL):	1.671
Half-life (T1/2):	0.172

ADMET: Toxicity

hERG Blockers:	0.743
Human Hepatotoxicity (H-HT):	0.365
Drug-inuced Liver Injury (DILI):	0.869
AMES Toxicity:	0.179
Rat Oral Acute Toxicity:	0.03
Maximum Recommended Daily Dose:	0.787
Skin Sensitization:	0.962
Carcinogencity:	0.22
Eye Corrosion:	0.025
Eye Irritation:	0.215
Respiratory Toxicity:	0.965

Download Data

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

Natural Product: NPC157739

Natural Product ID:	NPC157739
*Common Name:**	Stereonsteroid D
IUPAC Name:	[(3S,5S,8S,9S,10R,13R,14S,17R)-3-[(2R,3S,4S,5S,6S)-5-acetyloxy-3,4-dihydroxy-6-methyloxan-2-yl]oxy-17-ethenyl-13-methyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-10-yl]methyl acetate
Synonyms:	Stereonsteroid D
Standard InCHIKey:	ZIRCQXRSWINRFQ-VBWNICJHSA-N
Standard InCHI:	InChI=1S/C31H48O8/c1-6-20-8-10-24-23-9-7-21-15-22(39-29-27(35)26(34)28(17(2)37-29)38-19(4)33)11-14-31(21,16-36-18(3)32)25(23)12-13-30(20,24)5/h6,17,20-29,34-35H,1,7-16H2,2-5H3/t17-,20-,21-,22-,23-,24-,25-,26-,27-,28+,29-,30+,31+/m0/s1
SMILES:	C=C[C@H]1CC[C@H]2[C@@H]3CC[C@H]4C[C@H](CC[C@]4(COC(=O)C)[C@H]3CC[C@]12C)O[C@H]1[C@H]([C@@H]([C@@H]([C@H](C)O1)OC(=O)C)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL500466
PubChem CID:	11620917
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001013] Steroidal glycosides

*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
NPO33076	stereonephthya crystalliana	Species	Nephtheidae	Eukaryota	n.a.	formosan soft coral	n.a.	PMID[16441077]

☑ 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
ED50	1
IC50	1

Activity Type	# Activity
Cell Line	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT139	Cell Line	HT-29	Homo sapiens	ED50	=	5.2	ug ml-1	PMID[574185]
NPT168	Cell Line	P388	Mus musculus	IC50	=	4.9	ug.mL-1	PMID[574185]

☑ 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 NPC157739 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	209
0.1-0.2	1916
0.2-0.3	6542
0.3-0.4	13636
0.4-0.5	8297
0.5-0.6	5126
0.6-0.7	4069
0.7-0.8	2374
0.8-0.85	429
0.85-0.9	90
0.9-0.95	4
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
0.989	High Similarity	NPC471770
0.989	High Similarity	NPC473555
0.989	High Similarity	NPC278939
0.9677	High Similarity	NPC317019
0.9341	High Similarity	NPC48463
0.9184	High Similarity	NPC473199
0.9091	High Similarity	NPC234160
0.9072	High Similarity	NPC154452
0.9	High Similarity	NPC472988
0.9	High Similarity	NPC230888
0.9	High Similarity	NPC38217
0.899	High Similarity	NPC165405
0.8969	High Similarity	NPC21064
0.8969	High Similarity	NPC121072
0.8947	High Similarity	NPC472989
0.8911	High Similarity	NPC125361
0.8911	High Similarity	NPC43976
0.8911	High Similarity	NPC51925
0.8911	High Similarity	NPC296761
0.8911	High Similarity	NPC154085
0.8878	High Similarity	NPC94919
0.8866	High Similarity	NPC473200
0.8866	High Similarity	NPC7341
0.8812	High Similarity	NPC88744
0.8776	High Similarity	NPC88000
0.8776	High Similarity	NPC309425
0.8776	High Similarity	NPC4831
0.8776	High Similarity	NPC129372
0.8776	High Similarity	NPC472023
0.8776	High Similarity	NPC160734
0.8776	High Similarity	NPC47566
0.8763	High Similarity	NPC234287
0.8763	High Similarity	NPC280825
0.8738	High Similarity	NPC65167
0.8738	High Similarity	NPC114188
0.8725	High Similarity	NPC51947
0.8725	High Similarity	NPC91583
0.8725	High Similarity	NPC240125
0.8725	High Similarity	NPC473844
0.8713	High Similarity	NPC470169
0.8713	High Similarity	NPC470170
0.87	High Similarity	NPC312774
0.87	High Similarity	NPC475365
0.8687	High Similarity	NPC312553
0.8687	High Similarity	NPC136816
0.8687	High Similarity	NPC288694
0.8687	High Similarity	NPC159036
0.866	High Similarity	NPC76486
0.8627	High Similarity	NPC295980
0.86	High Similarity	NPC245280
0.86	High Similarity	NPC211879
0.86	High Similarity	NPC8039
0.86	High Similarity	NPC473198
0.86	High Similarity	NPC157659
0.86	High Similarity	NPC120123
0.86	High Similarity	NPC31907
0.86	High Similarity	NPC189852
0.86	High Similarity	NPC155010
0.86	High Similarity	NPC16573
0.86	High Similarity	NPC213190
0.86	High Similarity	NPC131479
0.86	High Similarity	NPC473020
0.86	High Similarity	NPC114874
0.86	High Similarity	NPC286969
0.86	High Similarity	NPC472252
0.86	High Similarity	NPC16520
0.8586	High Similarity	NPC31346
0.8571	High Similarity	NPC144068
0.8571	High Similarity	NPC158088
0.8571	High Similarity	NPC477928
0.8558	High Similarity	NPC204392
0.8558	High Similarity	NPC11035
0.8558	High Similarity	NPC263827
0.8558	High Similarity	NPC285410
0.8558	High Similarity	NPC1876
0.8558	High Similarity	NPC240734
0.8558	High Similarity	NPC91838
0.8558	High Similarity	NPC250481
0.8558	High Similarity	NPC275668
0.8558	High Similarity	NPC272242
0.8557	High Similarity	NPC207617
0.8542	High Similarity	NPC211238
0.8542	High Similarity	NPC151214
0.8542	High Similarity	NPC191915
0.8529	High Similarity	NPC287269
0.8515	High Similarity	NPC273879
0.8515	High Similarity	NPC85593
0.8515	High Similarity	NPC165033
0.8515	High Similarity	NPC31430
0.8515	High Similarity	NPC173583
0.85	High Similarity	NPC272015
0.85	High Similarity	NPC470053
0.8485	Intermediate Similarity	NPC91497
0.8485	Intermediate Similarity	NPC282669
0.8476	Intermediate Similarity	NPC470543
0.8476	Intermediate Similarity	NPC243572
0.8469	Intermediate Similarity	NPC473890
0.8469	Intermediate Similarity	NPC243728
0.8462	Intermediate Similarity	NPC129340
0.8454	Intermediate Similarity	NPC94582
0.8454	Intermediate Similarity	NPC57964
0.8447	Intermediate Similarity	NPC295389
0.8447	Intermediate Similarity	NPC224414
0.8447	Intermediate Similarity	NPC472897
0.8447	Intermediate Similarity	NPC472896
0.8438	Intermediate Similarity	NPC474835
0.8431	Intermediate Similarity	NPC127801
0.8431	Intermediate Similarity	NPC472898
0.8431	Intermediate Similarity	NPC269627
0.8431	Intermediate Similarity	NPC160816
0.8431	Intermediate Similarity	NPC472899
0.8431	Intermediate Similarity	NPC69737
0.8431	Intermediate Similarity	NPC152584
0.8431	Intermediate Similarity	NPC194842
0.8431	Intermediate Similarity	NPC208477
0.8431	Intermediate Similarity	NPC208594
0.8431	Intermediate Similarity	NPC472900
0.8416	Intermediate Similarity	NPC471467
0.8411	Intermediate Similarity	NPC199428
0.8411	Intermediate Similarity	NPC99620
0.8411	Intermediate Similarity	NPC5311
0.8411	Intermediate Similarity	NPC310341
0.8411	Intermediate Similarity	NPC193382
0.8404	Intermediate Similarity	NPC263079
0.84	Intermediate Similarity	NPC470054
0.84	Intermediate Similarity	NPC267510
0.8396	Intermediate Similarity	NPC102619
0.8396	Intermediate Similarity	NPC73986
0.8396	Intermediate Similarity	NPC146563
0.8384	Intermediate Similarity	NPC469725
0.8381	Intermediate Similarity	NPC470748
0.8367	Intermediate Similarity	NPC296936
0.8367	Intermediate Similarity	NPC252056
0.8367	Intermediate Similarity	NPC237071
0.8367	Intermediate Similarity	NPC238796
0.8367	Intermediate Similarity	NPC203434
0.8365	Intermediate Similarity	NPC473570
0.8365	Intermediate Similarity	NPC8431
0.8365	Intermediate Similarity	NPC265655
0.8351	Intermediate Similarity	NPC305160
0.835	Intermediate Similarity	NPC470166
0.835	Intermediate Similarity	NPC231340
0.835	Intermediate Similarity	NPC473469
0.835	Intermediate Similarity	NPC63368
0.835	Intermediate Similarity	NPC208650
0.835	Intermediate Similarity	NPC181467
0.835	Intermediate Similarity	NPC14946
0.8333	Intermediate Similarity	NPC243196
0.8333	Intermediate Similarity	NPC471354
0.8333	Intermediate Similarity	NPC470061
0.8333	Intermediate Similarity	NPC470062
0.8333	Intermediate Similarity	NPC27507
0.8333	Intermediate Similarity	NPC196429
0.8333	Intermediate Similarity	NPC470064
0.8333	Intermediate Similarity	NPC471353
0.8333	Intermediate Similarity	NPC474418
0.8333	Intermediate Similarity	NPC470058
0.8333	Intermediate Similarity	NPC309034
0.8333	Intermediate Similarity	NPC476361
0.8333	Intermediate Similarity	NPC34390
0.8333	Intermediate Similarity	NPC84987
0.8333	Intermediate Similarity	NPC158344
0.8333	Intermediate Similarity	NPC471351
0.8333	Intermediate Similarity	NPC93883
0.8333	Intermediate Similarity	NPC470043
0.8333	Intermediate Similarity	NPC99728
0.8333	Intermediate Similarity	NPC157376
0.8333	Intermediate Similarity	NPC470885
0.8333	Intermediate Similarity	NPC470057
0.8333	Intermediate Similarity	NPC470059
0.8333	Intermediate Similarity	NPC475521
0.8333	Intermediate Similarity	NPC77319
0.8333	Intermediate Similarity	NPC187400
0.8333	Intermediate Similarity	NPC470060
0.8333	Intermediate Similarity	NPC75608
0.8333	Intermediate Similarity	NPC50305
0.8333	Intermediate Similarity	NPC152615
0.8333	Intermediate Similarity	NPC244402
0.8333	Intermediate Similarity	NPC471355
0.8333	Intermediate Similarity	NPC142066
0.8333	Intermediate Similarity	NPC219516
0.8333	Intermediate Similarity	NPC87250
0.8333	Intermediate Similarity	NPC221562
0.8333	Intermediate Similarity	NPC476360
0.8333	Intermediate Similarity	NPC473852
0.8318	Intermediate Similarity	NPC69576
0.8318	Intermediate Similarity	NPC54395
0.8318	Intermediate Similarity	NPC469821
0.8318	Intermediate Similarity	NPC84949
0.8318	Intermediate Similarity	NPC31354
0.8318	Intermediate Similarity	NPC471633
0.8317	Intermediate Similarity	NPC177701
0.8317	Intermediate Similarity	NPC31085
0.8302	Intermediate Similarity	NPC473125
0.83	Intermediate Similarity	NPC471247
0.8298	Intermediate Similarity	NPC140446
0.8298	Intermediate Similarity	NPC43912
0.8286	Intermediate Similarity	NPC106760
0.8286	Intermediate Similarity	NPC472717
0.8283	Intermediate Similarity	NPC210157

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 NPC157739 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	183
0.1-0.2	2268
0.2-0.3	4170
0.3-0.4	1624
0.4-0.5	443
0.5-0.6	299
0.6-0.7	133
0.7-0.8	18
0.8-0.85	12
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8257	Intermediate Similarity	NPD7328	Approved
0.8257	Intermediate Similarity	NPD7327	Approved
0.8224	Intermediate Similarity	NPD8133	Approved
0.8182	Intermediate Similarity	NPD7516	Approved
0.8108	Intermediate Similarity	NPD8294	Approved
0.8108	Intermediate Similarity	NPD8377	Approved
0.8036	Intermediate Similarity	NPD8380	Approved
0.8036	Intermediate Similarity	NPD8379	Approved
0.8036	Intermediate Similarity	NPD8296	Approved
0.8036	Intermediate Similarity	NPD8033	Approved
0.8036	Intermediate Similarity	NPD8335	Approved
0.8036	Intermediate Similarity	NPD8378	Approved
0.7879	Intermediate Similarity	NPD8171	Discontinued
0.7876	Intermediate Similarity	NPD7503	Approved
0.783	Intermediate Similarity	NPD6412	Phase 2
0.7759	Intermediate Similarity	NPD7507	Approved
0.7593	Intermediate Similarity	NPD6686	Approved
0.7563	Intermediate Similarity	NPD7319	Approved
0.7523	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7477	Intermediate Similarity	NPD8170	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD6928	Phase 2
0.7333	Intermediate Similarity	NPD7736	Approved
0.7288	Intermediate Similarity	NPD8328	Phase 3
0.7255	Intermediate Similarity	NPD8034	Phase 2
0.7255	Intermediate Similarity	NPD8035	Phase 2
0.7217	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7172	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD7638	Approved
0.7103	Intermediate Similarity	NPD7639	Approved
0.7103	Intermediate Similarity	NPD7640	Approved
0.7059	Intermediate Similarity	NPD6370	Approved
0.7018	Intermediate Similarity	NPD6882	Approved
0.701	Intermediate Similarity	NPD7525	Registered
0.6983	Remote Similarity	NPD6940	Discontinued
0.6967	Remote Similarity	NPD8293	Discontinued
0.6964	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6942	Remote Similarity	NPD7492	Approved
0.6923	Remote Similarity	NPD6009	Approved
0.6891	Remote Similarity	NPD6054	Approved
0.6891	Remote Similarity	NPD6319	Approved
0.6885	Remote Similarity	NPD6616	Approved
0.687	Remote Similarity	NPD8297	Approved
0.6857	Remote Similarity	NPD6399	Phase 3
0.6829	Remote Similarity	NPD7078	Approved
0.681	Remote Similarity	NPD4632	Approved
0.6804	Remote Similarity	NPD6697	Approved
0.6804	Remote Similarity	NPD6118	Approved
0.6804	Remote Similarity	NPD6115	Approved
0.6804	Remote Similarity	NPD6114	Approved
0.675	Remote Similarity	NPD6059	Approved
0.6701	Remote Similarity	NPD6116	Phase 1
0.6699	Remote Similarity	NPD7524	Approved
0.6694	Remote Similarity	NPD6016	Approved
0.6694	Remote Similarity	NPD6015	Approved
0.6667	Remote Similarity	NPD6881	Approved
0.6667	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6899	Approved
0.6639	Remote Similarity	NPD5988	Approved
0.6639	Remote Similarity	NPD7115	Discovery
0.6638	Remote Similarity	NPD6649	Approved
0.6638	Remote Similarity	NPD6650	Approved
0.6637	Remote Similarity	NPD6402	Approved
0.6637	Remote Similarity	NPD5739	Approved
0.6637	Remote Similarity	NPD7128	Approved
0.6637	Remote Similarity	NPD6675	Approved
0.6634	Remote Similarity	NPD3669	Approved
0.6634	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.6609	Remote Similarity	NPD6372	Approved
0.6609	Remote Similarity	NPD6373	Approved
0.6604	Remote Similarity	NPD7637	Suspended
0.6598	Remote Similarity	NPD6117	Approved
0.6585	Remote Similarity	NPD6067	Discontinued
0.6579	Remote Similarity	NPD5697	Approved
0.6569	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6566	Remote Similarity	NPD7645	Phase 2
0.6562	Remote Similarity	NPD8449	Approved
0.6562	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6557	Remote Similarity	NPD8517	Approved
0.6557	Remote Similarity	NPD8513	Phase 3
0.6557	Remote Similarity	NPD8515	Approved
0.6557	Remote Similarity	NPD8516	Approved
0.6552	Remote Similarity	NPD7102	Approved
0.6552	Remote Similarity	NPD7290	Approved
0.6552	Remote Similarity	NPD6883	Approved
0.6544	Remote Similarity	NPD7625	Phase 1
0.6522	Remote Similarity	NPD7320	Approved
0.6518	Remote Similarity	NPD7632	Discontinued
0.6512	Remote Similarity	NPD8450	Suspended
0.6496	Remote Similarity	NPD8130	Phase 1
0.6496	Remote Similarity	NPD6617	Approved
0.6496	Remote Similarity	NPD6847	Approved
0.6496	Remote Similarity	NPD6869	Approved
0.6495	Remote Similarity	NPD6942	Approved
0.6495	Remote Similarity	NPD7339	Approved
0.6481	Remote Similarity	NPD7748	Approved
0.6471	Remote Similarity	NPD6695	Phase 3
0.6466	Remote Similarity	NPD6014	Approved
0.6466	Remote Similarity	NPD6013	Approved
0.6466	Remote Similarity	NPD6012	Approved
0.6455	Remote Similarity	NPD6084	Phase 2
0.6455	Remote Similarity	NPD6083	Phase 2
0.6455	Remote Similarity	NPD7902	Approved
0.6452	Remote Similarity	NPD7604	Phase 2
0.6449	Remote Similarity	NPD7515	Phase 2
0.6435	Remote Similarity	NPD5701	Approved
0.6423	Remote Similarity	NPD5983	Phase 2
0.6423	Remote Similarity	NPD6921	Approved
0.6422	Remote Similarity	NPD7991	Discontinued
0.6421	Remote Similarity	NPD7532	Clinical (unspecified phase)
0.6408	Remote Similarity	NPD4786	Approved
0.6396	Remote Similarity	NPD4225	Approved
0.6392	Remote Similarity	NPD1810	Approved
0.6392	Remote Similarity	NPD1811	Approved
0.6379	Remote Similarity	NPD6011	Approved
0.6356	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6349	Remote Similarity	NPD6336	Discontinued
0.6325	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6321	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6296	Remote Similarity	NPD6079	Approved
0.6283	Remote Similarity	NPD5344	Discontinued
0.6271	Remote Similarity	NPD4634	Approved
0.6263	Remote Similarity	NPD6933	Approved
0.6263	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6262	Remote Similarity	NPD5328	Approved
0.6262	Remote Similarity	NPD6051	Approved
0.625	Remote Similarity	NPD6033	Approved
0.6239	Remote Similarity	NPD8174	Phase 2
0.6238	Remote Similarity	NPD6929	Approved
0.6226	Remote Similarity	NPD7750	Discontinued
0.6218	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6214	Remote Similarity	NPD3667	Approved
0.6207	Remote Similarity	NPD6008	Approved
0.62	Remote Similarity	NPD6932	Approved
0.6195	Remote Similarity	NPD5286	Approved
0.6195	Remote Similarity	NPD5285	Approved
0.6195	Remote Similarity	NPD4696	Approved
0.6186	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6186	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6182	Remote Similarity	NPD7900	Approved
0.6182	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6176	Remote Similarity	NPD6930	Phase 2
0.6176	Remote Similarity	NPD6931	Approved
0.6168	Remote Similarity	NPD6672	Approved
0.6168	Remote Similarity	NPD5737	Approved
0.6161	Remote Similarity	NPD4755	Approved
0.6154	Remote Similarity	NPD4788	Approved
0.6147	Remote Similarity	NPD6411	Approved
0.6139	Remote Similarity	NPD7145	Approved
0.6134	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6132	Remote Similarity	NPD6684	Approved
0.6132	Remote Similarity	NPD7521	Approved
0.6132	Remote Similarity	NPD5330	Approved
0.6132	Remote Similarity	NPD7334	Approved
0.6132	Remote Similarity	NPD6409	Approved
0.6132	Remote Similarity	NPD7146	Approved
0.6132	Remote Similarity	NPD3618	Phase 1
0.6129	Remote Similarity	NPD7100	Approved
0.6129	Remote Similarity	NPD7101	Approved
0.6126	Remote Similarity	NPD5695	Phase 3
0.6106	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6106	Remote Similarity	NPD5696	Approved
0.6091	Remote Similarity	NPD4202	Approved
0.6087	Remote Similarity	NPD5211	Phase 2
0.6087	Remote Similarity	NPD5225	Approved
0.6087	Remote Similarity	NPD5224	Approved
0.6087	Remote Similarity	NPD4633	Approved
0.6087	Remote Similarity	NPD5226	Approved
0.6082	Remote Similarity	NPD2687	Approved
0.6082	Remote Similarity	NPD2254	Approved
0.6082	Remote Similarity	NPD2686	Approved
0.6075	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6071	Remote Similarity	NPD5221	Approved
0.6071	Remote Similarity	NPD5222	Approved
0.6071	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6061	Remote Similarity	NPD6926	Approved
0.6061	Remote Similarity	NPD6924	Approved
0.6055	Remote Similarity	NPD7838	Discovery
0.6055	Remote Similarity	NPD6698	Approved
0.6055	Remote Similarity	NPD46	Approved
0.6053	Remote Similarity	NPD4700	Approved
0.6048	Remote Similarity	NPD6335	Approved
0.604	Remote Similarity	NPD6925	Approved
0.604	Remote Similarity	NPD5776	Phase 2
0.6034	Remote Similarity	NPD5175	Approved
0.6034	Remote Similarity	NPD5174	Approved
0.6031	Remote Similarity	NPD5956	Approved
0.602	Remote Similarity	NPD7150	Approved
0.602	Remote Similarity	NPD7152	Approved
0.602	Remote Similarity	NPD7151	Approved
0.6019	Remote Similarity	NPD6903	Approved
0.6019	Remote Similarity	NPD7514	Phase 3
0.6018	Remote Similarity	NPD5173	Approved
0.6016	Remote Similarity	NPD6868	Approved
0.6016	Remote Similarity	NPD6274	Approved
0.6	Remote Similarity	NPD7087	Discontinued
0.6	Remote Similarity	NPD5223	Approved
0.6	Remote Similarity	NPD3702	Approved
0.6	Remote Similarity	NPD3703	Phase 2
0.5983	Remote Similarity	NPD5141	Approved
0.5979	Remote Similarity	NPD3700	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