NPASS Compound

Structure

NPC475556 OpenBabel07101719522D 48 54 0 0 1 0 0 0 0 0999 V2000 6.9282 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4067 -1.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5388 -0.5000 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 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9511 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2111 -2.5691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 2.0000 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 10.3923 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6723 -3.0691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.2601 -2.2601 0.0000 C 0 0 0 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 -0.9511 -1.3090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 7.7942 1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 10.3923 2.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.2111 -3.5691 0.0000 C 0 0 0 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 11.2583 1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 11.2583 0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 10.3923 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 7.7942 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 9.5263 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 -0.0000 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 11.2583 3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 8.6603 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.0201 -4.1569 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 12.1244 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 12.1244 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 10.3923 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.4067 0.9135 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2601 -3.8781 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 9.5263 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 8.6603 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 32 1 0 0 0 0 3 33 1 0 0 0 0 4 8 1 0 0 0 0 4 19 1 0 0 0 0 5 9 1 0 0 0 0 5 21 1 0 0 0 0 6 10 1 0 0 0 0 6 22 1 0 0 0 0 7 11 1 0 0 0 0 7 20 1 0 0 0 0 8 32 1 0 0 0 0 9 33 1 0 0 0 0 10 34 1 0 0 0 0 11 35 1 0 0 0 0 12 18 2 0 0 0 0 12 25 1 0 0 0 0 13 23 1 0 0 0 0 13 26 1 0 0 0 0 14 19 1 0 0 0 0 14 34 1 0 0 0 0 15 36 1 0 0 0 0 16 18 1 0 0 0 0 16 44 1 0 0 0 0 17 1 1 1 0 0 0 17 30 1 0 0 0 0 17 45 1 0 0 0 0 18 20 1 0 0 0 0 19 46 1 1 0 0 0 20 33 1 1 0 0 0 21 22 1 0 0 0 0 21 32 1 1 0 0 0 22 35 1 6 0 0 0 23 30 1 0 0 0 0 23 37 1 1 0 0 0 24 15 1 6 0 0 0 24 27 1 0 0 0 0 24 47 1 0 0 0 0 25 38 2 0 0 0 0 25 44 1 0 0 0 0 26 45 1 0 0 0 0 26 46 1 1 0 0 0 27 28 1 0 0 0 0 27 39 1 1 0 0 0 28 29 1 0 0 0 0 28 40 1 6 0 0 0 29 31 1 0 0 0 0 29 41 1 1 0 0 0 30 48 1 6 0 0 0 31 47 1 0 0 0 0 31 48 1 6 0 0 0 32 34 1 1 0 0 0 33 35 1 1 0 0 0 34 42 1 1 0 0 0 35 43 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	682.36
Volume:	663.021
LogP:	1.519
LogD:	0.835
LogS:	-3.26
# Rotatable Bonds:	6
TPSA:	211.9
# H-Bond Aceptor:	13
# H-Bond Donor:	8
# Rings:	7
# Heavy Atoms:	13

MedChem Properties

QED Drug-Likeness Score:	0.2
Synthetic Accessibility Score:	5.761
Fsp3:	0.886
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.357
MDCK Permeability:	5.841556776431389e-05
Pgp-inhibitor:	0.057
Pgp-substrate:	0.999
Human Intestinal Absorption (HIA):	0.89
20% Bioavailability (F20%):	0.928
30% Bioavailability (F30%):	0.995

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.135
Plasma Protein Binding (PPB):	85.51171112060547%
Volume Distribution (VD):	0.264
Pgp-substrate:	10.816814422607422%

ADMET: Metabolism

CYP1A2-inhibitor:	0.002
CYP1A2-substrate:	0.935
CYP2C19-inhibitor:	0.003
CYP2C19-substrate:	0.266
CYP2C9-inhibitor:	0.006
CYP2C9-substrate:	0.044
CYP2D6-inhibitor:	0.004
CYP2D6-substrate:	0.082
CYP3A4-inhibitor:	0.162
CYP3A4-substrate:	0.17

ADMET: Excretion

Clearance (CL):	0.94
Half-life (T1/2):	0.631

ADMET: Toxicity

hERG Blockers:	0.274
Human Hepatotoxicity (H-HT):	0.275
Drug-inuced Liver Injury (DILI):	0.018
AMES Toxicity:	0.211
Rat Oral Acute Toxicity:	0.639
Maximum Recommended Daily Dose:	0.965
Skin Sensitization:	0.5
Carcinogencity:	0.364
Eye Corrosion:	0.003
Eye Irritation:	0.008
Respiratory Toxicity:	0.961

Download Data

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

Natural Product: NPC475556

Natural Product ID:	NPC475556
*Common Name:**	Corchorusoside C
IUPAC Name:	3-[(3S,5S,8R,9S,10R,13R,14S,17R)-5,14-dihydroxy-3-[(2R,4R,5S,6R)-4-hydroxy-6-methyl-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-10,13-dimethyl-2,3,4,6,7,8,9,11,12,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]-2H-furan-5-one
Synonyms:	Corchorusoside C
Standard InCHIKey:	ZOSJMTBTUZXPSR-YLGHRFGMSA-N
Standard InCHI:	InChI=1S/C35H54O13/c1-17-30(48-31-29(41)28(40)27(39)24(15-36)47-31)23(37)13-26(45-17)46-19-4-8-32(2)21-5-9-33(3)20(18-12-25(38)44-16-18)7-11-35(33,43)22(21)6-10-34(32,42)14-19/h12,17,19-24,26-31,36-37,39-43H,4-11,13-16H2,1-3H3/t17-,19+,20-,21+,22-,23-,24-,26+,27-,28+,29-,30-,31+,32-,33-,34+,35+/m1/s1
SMILES:	OC[C@H]1O[C@@H](O[C@H]2[C@H](O)C[C@@H](O[C@@H]2C)O[C@H]2CC[C@]3([C@](C2)(O)CC[C@@H]2[C@@H]3CC[C@]3([C@]2(O)CC[C@@H]3C2=CC(=O)OC2)C)C)[C@@H]([C@H]([C@@H]1O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL508079
PubChem CID:	44566921
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001125] Steroid lactones [CHEMONTID:0001555] Cardenolides and derivatives [CHEMONTID:0001559] Cardenolide glycosides and derivatives

*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
NPO32958	Streptocaulon juventas	Species	Apocynaceae	Eukaryota	n.a.	Vietnamese	n.a.	PMID[14640513]
NPO32958	Streptocaulon juventas	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31120251]

☑ 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	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT453	Cell Line	HT-1080	Homo sapiens	IC50	=	92.0	nM	PMID[489587]

☑ 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 NPC475556 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	269
0.1-0.2	1866
0.2-0.3	5401
0.3-0.4	11674
0.4-0.5	9914
0.5-0.6	6536
0.6-0.7	4041
0.7-0.8	1948
0.8-0.85	659
0.85-0.9	221
0.9-0.95	83
0.95-1	85

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC475629
0.991	High Similarity	NPC314535
0.991	High Similarity	NPC173555
0.9909	High Similarity	NPC292467
0.9909	High Similarity	NPC32177
0.9909	High Similarity	NPC470897
0.9909	High Similarity	NPC236973
0.9909	High Similarity	NPC55532
0.9909	High Similarity	NPC469756
0.9909	High Similarity	NPC30483
0.9821	High Similarity	NPC264336
0.982	High Similarity	NPC475136
0.982	High Similarity	NPC72260
0.982	High Similarity	NPC474466
0.9735	High Similarity	NPC208193
0.9735	High Similarity	NPC308262
0.9735	High Similarity	NPC117445
0.9732	High Similarity	NPC231518
0.9732	High Similarity	NPC475590
0.9732	High Similarity	NPC474908
0.9732	High Similarity	NPC475219
0.9732	High Similarity	NPC40749
0.9732	High Similarity	NPC120390
0.9732	High Similarity	NPC475419
0.973	High Similarity	NPC329905
0.9727	High Similarity	NPC471351
0.9727	High Similarity	NPC309034
0.9727	High Similarity	NPC99728
0.9727	High Similarity	NPC84987
0.9727	High Similarity	NPC27507
0.9727	High Similarity	NPC196429
0.9727	High Similarity	NPC471354
0.9727	High Similarity	NPC244402
0.9727	High Similarity	NPC34390
0.9727	High Similarity	NPC474418
0.9727	High Similarity	NPC158344
0.9727	High Similarity	NPC157376
0.9727	High Similarity	NPC87250
0.9727	High Similarity	NPC50305
0.9727	High Similarity	NPC471353
0.9727	High Similarity	NPC473852
0.9727	High Similarity	NPC77319
0.9727	High Similarity	NPC243196
0.9727	High Similarity	NPC93883
0.9727	High Similarity	NPC142066
0.9727	High Similarity	NPC471355
0.9646	High Similarity	NPC74259
0.9646	High Similarity	NPC193893
0.9646	High Similarity	NPC474423
0.964	High Similarity	NPC83287
0.9636	High Similarity	NPC5311
0.9636	High Similarity	NPC193382
0.9636	High Similarity	NPC99620
0.9636	High Similarity	NPC199428
0.9636	High Similarity	NPC310341
0.9554	High Similarity	NPC44899
0.9554	High Similarity	NPC304260
0.9554	High Similarity	NPC5883
0.9554	High Similarity	NPC29639
0.955	High Similarity	NPC152615
0.9545	High Similarity	NPC69576
0.9545	High Similarity	NPC31354
0.9545	High Similarity	NPC471633
0.9545	High Similarity	NPC84949
0.9469	High Similarity	NPC107607
0.9464	High Similarity	NPC218093
0.9381	High Similarity	NPC291820
0.9381	High Similarity	NPC81222
0.9375	High Similarity	NPC290693
0.9375	High Similarity	NPC203862
0.9316	High Similarity	NPC329784
0.9316	High Similarity	NPC240070
0.916	High Similarity	NPC140092
0.916	High Similarity	NPC232785
0.916	High Similarity	NPC329986
0.916	High Similarity	NPC125077
0.916	High Similarity	NPC188234
0.916	High Similarity	NPC276838
0.9138	High Similarity	NPC115349
0.913	High Similarity	NPC135369
0.9091	High Similarity	NPC469749
0.9091	High Similarity	NPC475030
0.9091	High Similarity	NPC247190
0.9091	High Similarity	NPC116075
0.9091	High Similarity	NPC146857
0.9091	High Similarity	NPC32793
0.906	High Similarity	NPC27363
0.9016	High Similarity	NPC329636
0.9008	High Similarity	NPC93416
0.9	High Similarity	NPC38217
0.9	High Similarity	NPC472988
0.8992	High Similarity	NPC471357
0.8992	High Similarity	NPC469757
0.8992	High Similarity	NPC146456
0.8992	High Similarity	NPC471356
0.8992	High Similarity	NPC117702
0.8992	High Similarity	NPC179412
0.8966	High Similarity	NPC470312
0.8957	High Similarity	NPC475403
0.8957	High Similarity	NPC160888
0.8947	High Similarity	NPC207637
0.8943	High Similarity	NPC194716
0.8934	High Similarity	NPC477709
0.8934	High Similarity	NPC476221
0.8929	High Similarity	NPC114188
0.8926	High Similarity	NPC253456
0.8926	High Similarity	NPC16569
0.8926	High Similarity	NPC159338
0.8919	High Similarity	NPC125361
0.8919	High Similarity	NPC43976
0.8919	High Similarity	NPC51925
0.8919	High Similarity	NPC296761
0.8919	High Similarity	NPC154085
0.8909	High Similarity	NPC234160
0.8908	High Similarity	NPC469750
0.8908	High Similarity	NPC250556
0.8879	High Similarity	NPC229962
0.8879	High Similarity	NPC195560
0.8879	High Similarity	NPC473633
0.8879	High Similarity	NPC268326
0.8879	High Similarity	NPC153085
0.8879	High Similarity	NPC476085
0.8871	High Similarity	NPC329675
0.8871	High Similarity	NPC59288
0.887	High Similarity	NPC20979
0.887	High Similarity	NPC476690
0.887	High Similarity	NPC100048
0.8852	High Similarity	NPC42670
0.8852	High Similarity	NPC19124
0.8843	High Similarity	NPC471360
0.8843	High Similarity	NPC180079
0.8843	High Similarity	NPC471358
0.8843	High Similarity	NPC86159
0.8843	High Similarity	NPC469754
0.8843	High Similarity	NPC284406
0.8843	High Similarity	NPC469751
0.8843	High Similarity	NPC10823
0.8843	High Similarity	NPC91
0.8843	High Similarity	NPC471359
0.8843	High Similarity	NPC9499
0.8843	High Similarity	NPC197707
0.8843	High Similarity	NPC251866
0.8843	High Similarity	NPC6108
0.8843	High Similarity	NPC70542
0.8843	High Similarity	NPC219085
0.8843	High Similarity	NPC469753
0.8843	High Similarity	NPC17896
0.8843	High Similarity	NPC471352
0.8843	High Similarity	NPC89514
0.8843	High Similarity	NPC469752
0.8843	High Similarity	NPC471361
0.8843	High Similarity	NPC469755
0.8818	High Similarity	NPC473199
0.8814	High Similarity	NPC43842
0.8803	High Similarity	NPC50689
0.8803	High Similarity	NPC198325
0.8803	High Similarity	NPC233391
0.8803	High Similarity	NPC207243
0.8793	High Similarity	NPC10366
0.878	High Similarity	NPC225385
0.878	High Similarity	NPC298783
0.878	High Similarity	NPC157817
0.878	High Similarity	NPC104585
0.878	High Similarity	NPC142756
0.8772	High Similarity	NPC144068
0.8761	High Similarity	NPC65167
0.8761	High Similarity	NPC13190
0.8761	High Similarity	NPC472987
0.8761	High Similarity	NPC473021
0.875	High Similarity	NPC250089
0.875	High Similarity	NPC14630
0.875	High Similarity	NPC157530
0.875	High Similarity	NPC179261
0.8739	High Similarity	NPC231340
0.8739	High Similarity	NPC295133
0.8739	High Similarity	NPC473469
0.8739	High Similarity	NPC106589
0.8739	High Similarity	NPC257207
0.8739	High Similarity	NPC202261
0.8684	High Similarity	NPC112274
0.8684	High Similarity	NPC473567
0.8684	High Similarity	NPC216595
0.8684	High Similarity	NPC475354
0.8673	High Similarity	NPC191439
0.8673	High Similarity	NPC170974
0.8673	High Similarity	NPC103627
0.8661	High Similarity	NPC295980
0.8655	High Similarity	NPC471082
0.8636	High Similarity	NPC120123
0.8636	High Similarity	NPC97487
0.8636	High Similarity	NPC131479
0.8636	High Similarity	NPC155010
0.8636	High Similarity	NPC196471
0.8636	High Similarity	NPC31907
0.8636	High Similarity	NPC187302
0.8636	High Similarity	NPC472252
0.8636	High Similarity	NPC157659
0.8636	High Similarity	NPC8039
0.8636	High Similarity	NPC211879
0.8636	High Similarity	NPC245280

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 NPC475556 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	232
0.1-0.2	1983
0.2-0.3	4136
0.3-0.4	1882
0.4-0.5	482
0.5-0.6	281
0.6-0.7	119
0.7-0.8	21
0.8-0.85	1
0.85-0.9	2
0.9-0.95	3
0.95-1	8

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.991	High Similarity	NPD8379	Approved
0.991	High Similarity	NPD8296	Approved
0.991	High Similarity	NPD8335	Approved
0.991	High Similarity	NPD8380	Approved
0.991	High Similarity	NPD8378	Approved
0.982	High Similarity	NPD8377	Approved
0.982	High Similarity	NPD8294	Approved
0.9732	High Similarity	NPD8033	Approved
0.964	High Similarity	NPD7327	Approved
0.964	High Similarity	NPD7328	Approved
0.9554	High Similarity	NPD7516	Approved
0.8908	High Similarity	NPD7507	Approved
0.8843	High Similarity	NPD7319	Approved
0.8729	High Similarity	NPD7503	Approved
0.8291	Intermediate Similarity	NPD8133	Approved
0.8017	Intermediate Similarity	NPD6686	Approved
0.781	Intermediate Similarity	NPD7625	Phase 1
0.7788	Intermediate Similarity	NPD7638	Approved
0.7778	Intermediate Similarity	NPD6412	Phase 2
0.7734	Intermediate Similarity	NPD7736	Approved
0.7719	Intermediate Similarity	NPD7639	Approved
0.7719	Intermediate Similarity	NPD7640	Approved
0.7559	Intermediate Similarity	NPD8328	Phase 3
0.7519	Intermediate Similarity	NPD8293	Discontinued
0.75	Intermediate Similarity	NPD8171	Discontinued
0.7355	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7344	Intermediate Similarity	NPD6370	Approved
0.7231	Intermediate Similarity	NPD7492	Approved
0.7222	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7213	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD6054	Approved
0.7188	Intermediate Similarity	NPD6059	Approved
0.7177	Intermediate Similarity	NPD8297	Approved
0.7177	Intermediate Similarity	NPD6882	Approved
0.7176	Intermediate Similarity	NPD6616	Approved
0.7167	Intermediate Similarity	NPD8170	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7632	Discontinued
0.7132	Intermediate Similarity	NPD8516	Approved
0.7132	Intermediate Similarity	NPD8517	Approved
0.7132	Intermediate Similarity	NPD8513	Phase 3
0.7132	Intermediate Similarity	NPD8515	Approved
0.7121	Intermediate Similarity	NPD7078	Approved
0.7087	Intermediate Similarity	NPD6009	Approved
0.7087	Intermediate Similarity	NPD7115	Discovery
0.7054	Intermediate Similarity	NPD6319	Approved
0.7016	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD6015	Approved
0.7	Intermediate Similarity	NPD6016	Approved
0.6992	Remote Similarity	NPD7320	Approved
0.6984	Remote Similarity	NPD4632	Approved
0.6967	Remote Similarity	NPD5739	Approved
0.6967	Remote Similarity	NPD6675	Approved
0.6967	Remote Similarity	NPD6402	Approved
0.6967	Remote Similarity	NPD7128	Approved
0.6947	Remote Similarity	NPD5988	Approved
0.6935	Remote Similarity	NPD6373	Approved
0.6935	Remote Similarity	NPD6372	Approved
0.6917	Remote Similarity	NPD5344	Discontinued
0.6894	Remote Similarity	NPD6067	Discontinued
0.6891	Remote Similarity	NPD4225	Approved
0.6861	Remote Similarity	NPD8449	Approved
0.6855	Remote Similarity	NPD6899	Approved
0.6855	Remote Similarity	NPD6881	Approved
0.6825	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6825	Remote Similarity	NPD6650	Approved
0.6825	Remote Similarity	NPD6649	Approved
0.6825	Remote Similarity	NPD8130	Phase 1
0.6812	Remote Similarity	NPD8450	Suspended
0.6783	Remote Similarity	NPD6051	Approved
0.6774	Remote Similarity	NPD5701	Approved
0.6774	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD5697	Approved
0.6772	Remote Similarity	NPD6053	Discontinued
0.675	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6746	Remote Similarity	NPD6883	Approved
0.6746	Remote Similarity	NPD7102	Approved
0.6746	Remote Similarity	NPD7290	Approved
0.6727	Remote Similarity	NPD7525	Registered
0.6695	Remote Similarity	NPD7748	Approved
0.6694	Remote Similarity	NPD6008	Approved
0.6693	Remote Similarity	NPD6847	Approved
0.6693	Remote Similarity	NPD6617	Approved
0.6693	Remote Similarity	NPD6869	Approved
0.6691	Remote Similarity	NPD6033	Approved
0.6667	Remote Similarity	NPD6083	Phase 2
0.6667	Remote Similarity	NPD6084	Phase 2
0.6667	Remote Similarity	NPD6014	Approved
0.6667	Remote Similarity	NPD6013	Approved
0.6667	Remote Similarity	NPD6012	Approved
0.6667	Remote Similarity	NPD7902	Approved
0.6642	Remote Similarity	NPD7604	Phase 2
0.6617	Remote Similarity	NPD5983	Phase 2
0.6609	Remote Similarity	NPD7524	Approved
0.6587	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6587	Remote Similarity	NPD6011	Approved
0.6577	Remote Similarity	NPD6928	Phase 2
0.6562	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6557	Remote Similarity	NPD6648	Approved
0.6544	Remote Similarity	NPD6336	Discontinued
0.6529	Remote Similarity	NPD4755	Approved
0.6525	Remote Similarity	NPD7515	Phase 2
0.6525	Remote Similarity	NPD8034	Phase 2
0.6525	Remote Similarity	NPD8035	Phase 2
0.6508	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6491	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6491	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6484	Remote Similarity	NPD4634	Approved
0.6471	Remote Similarity	NPD4202	Approved
0.6452	Remote Similarity	NPD5211	Phase 2
0.6441	Remote Similarity	NPD46	Approved
0.6441	Remote Similarity	NPD7838	Discovery
0.6441	Remote Similarity	NPD6698	Approved
0.6423	Remote Similarity	NPD4700	Approved
0.6423	Remote Similarity	NPD5286	Approved
0.6423	Remote Similarity	NPD4696	Approved
0.6423	Remote Similarity	NPD5285	Approved
0.6417	Remote Similarity	NPD7900	Approved
0.6417	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.641	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6404	Remote Similarity	NPD6695	Phase 3
0.6387	Remote Similarity	NPD7637	Suspended
0.638	Remote Similarity	NPD7799	Discontinued
0.6377	Remote Similarity	NPD8074	Phase 3
0.6371	Remote Similarity	NPD4159	Approved
0.6364	Remote Similarity	NPD6274	Approved
0.6364	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD5695	Phase 3
0.6357	Remote Similarity	NPD6371	Approved
0.6349	Remote Similarity	NPD5141	Approved
0.6343	Remote Similarity	NPD7101	Approved
0.6343	Remote Similarity	NPD7100	Approved
0.6341	Remote Similarity	NPD5696	Approved
0.6339	Remote Similarity	NPD7645	Phase 2
0.6333	Remote Similarity	NPD6399	Phase 3
0.6325	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6325	Remote Similarity	NPD7750	Discontinued
0.632	Remote Similarity	NPD5226	Approved
0.632	Remote Similarity	NPD4633	Approved
0.632	Remote Similarity	NPD5224	Approved
0.632	Remote Similarity	NPD5225	Approved
0.6299	Remote Similarity	NPD4767	Approved
0.6299	Remote Similarity	NPD4768	Approved
0.6293	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6271	Remote Similarity	NPD6903	Approved
0.627	Remote Similarity	NPD5174	Approved
0.627	Remote Similarity	NPD5175	Approved
0.6269	Remote Similarity	NPD6335	Approved
0.625	Remote Similarity	NPD6909	Approved
0.625	Remote Similarity	NPD6908	Approved
0.625	Remote Similarity	NPD5693	Phase 1
0.6241	Remote Similarity	NPD5956	Approved
0.624	Remote Similarity	NPD5223	Approved
0.6239	Remote Similarity	NPD6684	Approved
0.6239	Remote Similarity	NPD7334	Approved
0.6239	Remote Similarity	NPD7521	Approved
0.6239	Remote Similarity	NPD7146	Approved
0.6239	Remote Similarity	NPD6409	Approved
0.6239	Remote Similarity	NPD5330	Approved
0.6218	Remote Similarity	NPD5328	Approved
0.6218	Remote Similarity	NPD4753	Phase 2
0.6214	Remote Similarity	NPD8337	Approved
0.6214	Remote Similarity	NPD8336	Approved
0.6202	Remote Similarity	NPD4730	Approved
0.6202	Remote Similarity	NPD4729	Approved
0.6194	Remote Similarity	NPD6317	Approved
0.6154	Remote Similarity	NPD8338	Approved
0.6154	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6148	Remote Similarity	NPD6313	Approved
0.6148	Remote Similarity	NPD6314	Approved
0.6142	Remote Similarity	NPD4754	Approved
0.614	Remote Similarity	NPD6931	Approved
0.614	Remote Similarity	NPD6930	Phase 2
0.6131	Remote Similarity	NPD6921	Approved
0.6131	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6116	Remote Similarity	NPD6079	Approved
0.6107	Remote Similarity	NPD5247	Approved
0.6107	Remote Similarity	NPD5248	Approved
0.6107	Remote Similarity	NPD5250	Approved
0.6107	Remote Similarity	NPD5251	Approved
0.6107	Remote Similarity	NPD5249	Phase 3
0.6102	Remote Similarity	NPD3618	Phase 1
0.6083	Remote Similarity	NPD6080	Approved
0.6083	Remote Similarity	NPD6904	Approved
0.6083	Remote Similarity	NPD6673	Approved
0.6077	Remote Similarity	NPD5128	Approved
0.6071	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6068	Remote Similarity	NPD3665	Phase 1
0.6068	Remote Similarity	NPD3666	Approved
0.6068	Remote Similarity	NPD3133	Approved
0.6053	Remote Similarity	NPD6929	Approved
0.6053	Remote Similarity	NPD4195	Approved
0.6034	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6016	Remote Similarity	NPD6001	Approved
0.6	Remote Similarity	NPD5737	Approved
0.6	Remote Similarity	NPD6672	Approved
0.6	Remote Similarity	NPD6940	Discontinued
0.6	Remote Similarity	NPD7514	Phase 3
0.5984	Remote Similarity	NPD5284	Approved
0.5984	Remote Similarity	NPD5281	Approved
0.5984	Remote Similarity	NPD7087	Discontinued

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