NPASS Compound

Structure

NPC473517 OpenBabel07101718202D 42 47 0 0 1 0 0 0 0 0999 V2000 -2.4271 -2.7634 0.0000 C 0 0 0 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 6.8200 4.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.4181 0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8200 -1.6910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8966 -1.1045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0880 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7226 -1.1810 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3559 2.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2219 -0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3559 -0.6910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2219 2.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9135 -0.5933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5388 1.1180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9540 2.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7045 -2.5823 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6180 -2.1756 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 -1.3090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 7.6861 3.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.5521 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8200 -0.6910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3559 1.3090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.2219 0.8090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.4899 0.8090 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 6.8200 2.3090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.5388 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 6.8200 1.3090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.9540 0.8090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.4899 -0.1910 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.0880 1.3090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.0880 2.3090 0.0000 C 0 0 2 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 8.5521 4.3090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 8.5521 2.3090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.6861 -0.1910 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.0880 3.3090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.1045 -1.9945 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.6861 2.8090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.6861 0.8090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.9540 -0.1910 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 17 2 0 0 0 0 2 18 1 0 0 0 0 3 19 1 0 0 0 0 4 20 1 0 0 0 0 5 21 1 0 0 0 0 7 31 1 0 0 0 0 8 13 1 0 0 0 0 8 17 1 0 0 0 0 9 12 1 0 0 0 0 10 11 1 0 0 0 0 10 23 1 0 0 0 0 11 30 1 0 0 0 0 12 32 1 0 0 0 0 14 24 1 0 0 0 0 15 26 1 0 0 0 0 15 32 1 0 0 0 0 16 17 1 0 0 0 0 16 38 1 0 0 0 0 18 27 1 0 0 0 0 18 33 1 6 0 0 0 19 34 2 0 0 0 0 19 39 1 0 0 0 0 20 35 2 0 0 0 0 20 40 1 0 0 0 0 21 36 2 0 0 0 0 21 41 1 0 0 0 0 22 9 1 6 0 0 0 22 23 1 0 0 0 0 22 24 1 0 0 0 0 23 31 1 1 0 0 0 24 30 1 1 0 0 0 25 14 1 1 0 0 0 25 27 1 0 0 0 0 25 42 1 0 0 0 0 26 28 1 0 0 0 0 26 39 1 1 0 0 0 27 30 1 1 0 0 0 28 29 1 0 0 0 0 28 40 1 1 0 0 0 29 31 1 1 0 0 0 29 41 1 0 0 0 0 30 6 1 1 0 0 0 31 32 1 1 0 0 0 32 37 1 1 0 0 0 33 13 1 1 0 0 0 33 38 1 0 0 0 0 33 42 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	588.33
Volume:	596.551
LogP:	3.468
LogD:	3.047
LogS:	-4.282
# Rotatable Bonds:	6
TPSA:	117.59
# H-Bond Aceptor:	9
# H-Bond Donor:	1
# Rings:	6
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.289
Synthetic Accessibility Score:	5.952
Fsp3:	0.848
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:	-5.194
MDCK Permeability:	7.871502020861953e-05
Pgp-inhibitor:	0.895
Pgp-substrate:	0.005
Human Intestinal Absorption (HIA):	0.023
20% Bioavailability (F20%):	0.039
30% Bioavailability (F30%):	0.78

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.779
Plasma Protein Binding (PPB):	34.216434478759766%
Volume Distribution (VD):	1.143
Pgp-substrate:	49.166194915771484%

ADMET: Metabolism

CYP1A2-inhibitor:	0.019
CYP1A2-substrate:	0.074
CYP2C19-inhibitor:	0.01
CYP2C19-substrate:	0.113
CYP2C9-inhibitor:	0.011
CYP2C9-substrate:	0.008
CYP2D6-inhibitor:	0.612
CYP2D6-substrate:	0.065
CYP3A4-inhibitor:	0.875
CYP3A4-substrate:	0.308

ADMET: Excretion

Clearance (CL):	3.418
Half-life (T1/2):	0.288

ADMET: Toxicity

hERG Blockers:	0.953
Human Hepatotoxicity (H-HT):	0.869
Drug-inuced Liver Injury (DILI):	0.919
AMES Toxicity:	0.51
Rat Oral Acute Toxicity:	0.946
Maximum Recommended Daily Dose:	0.75
Skin Sensitization:	0.9
Carcinogencity:	0.745
Eye Corrosion:	0.04
Eye Irritation:	0.018
Respiratory Toxicity:	0.982

Download Data

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

Natural Product: NPC473517

Natural Product ID:	NPC473517
*Common Name:**	Tupichigenin Aa
IUPAC Name:	n.a.
Synonyms:	Tupichigenin Aa
Standard InCHIKey:	FNFPRXDTKCJEJB-GMUBKUCRSA-N
Standard InCHI:	InChI=1S/C33H48O9/c1-17-8-13-33(38-16-17)18(2)27-25(42-33)14-24-22-9-12-32(37)15-26(39-19(3)34)28(40-20(4)35)29(41-21(5)36)31(32,7)23(22)10-11-30(24,27)6/h18,22-29,37H,1,8-16H2,2-7H3/t18-,22+,23-,24-,25-,26+,27-,28+,29+,30-,31-,32-,33+/m0/s1
SMILES:	CC1C2C(CC3C2(CCC4C3CCC5(C4(C(C(C(C5)OC(=O)C)OC(=O)C)OC(=O)C)C)O)C)OC16CCC(=C)CO6
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL444455
PubChem CID:	11124786
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
NPO31092	Tupistra chinensis	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12608845]
NPO31092	Tupistra chinensis	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]

☑ 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
Others	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT4162	Cell Line	NUGC	Homo sapiens	Inhibition	=	50.0	%	PMID[561866]

☑ 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 NPC473517 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	275
0.1-0.2	2257
0.2-0.3	6561
0.3-0.4	13878
0.4-0.5	8125
0.5-0.6	5507
0.6-0.7	4037
0.7-0.8	1786
0.8-0.85	253
0.85-0.9	13
0.9-0.95	3
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9703	High Similarity	NPC473570
0.9109	High Similarity	NPC228049
0.9109	High Similarity	NPC52585
0.9109	High Similarity	NPC68630
0.8738	High Similarity	NPC177701
0.8713	High Similarity	NPC274793
0.8654	High Similarity	NPC471467
0.8649	High Similarity	NPC83287
0.8641	High Similarity	NPC49532
0.8585	High Similarity	NPC470169
0.8585	High Similarity	NPC54619
0.8585	High Similarity	NPC470170
0.8559	High Similarity	NPC87250
0.8559	High Similarity	NPC77319
0.8559	High Similarity	NPC152615
0.8559	High Similarity	NPC158344
0.8559	High Similarity	NPC471353
0.8559	High Similarity	NPC473852
0.8559	High Similarity	NPC27507
0.8559	High Similarity	NPC243196
0.8559	High Similarity	NPC157376
0.8559	High Similarity	NPC196429
0.8559	High Similarity	NPC309034
0.8559	High Similarity	NPC34390
0.8559	High Similarity	NPC474418
0.8559	High Similarity	NPC471351
0.8559	High Similarity	NPC93883
0.8559	High Similarity	NPC471355
0.8559	High Similarity	NPC84987
0.8559	High Similarity	NPC471354
0.8559	High Similarity	NPC244402
0.8559	High Similarity	NPC99728
0.8559	High Similarity	NPC142066
0.8559	High Similarity	NPC50305
0.8558	High Similarity	NPC31085
0.8515	High Similarity	NPC241047
0.8509	High Similarity	NPC264336
0.8496	Intermediate Similarity	NPC474466
0.8496	Intermediate Similarity	NPC475136
0.8496	Intermediate Similarity	NPC475556
0.8496	Intermediate Similarity	NPC475629
0.8468	Intermediate Similarity	NPC193382
0.8468	Intermediate Similarity	NPC199428
0.8468	Intermediate Similarity	NPC99620
0.8468	Intermediate Similarity	NPC5311
0.8468	Intermediate Similarity	NPC310341
0.8455	Intermediate Similarity	NPC102619
0.8455	Intermediate Similarity	NPC144068
0.8447	Intermediate Similarity	NPC469725
0.8431	Intermediate Similarity	NPC306797
0.8431	Intermediate Similarity	NPC169270
0.8431	Intermediate Similarity	NPC292718
0.8431	Intermediate Similarity	NPC111834
0.8426	Intermediate Similarity	NPC475030
0.8426	Intermediate Similarity	NPC151134
0.8421	Intermediate Similarity	NPC173555
0.8421	Intermediate Similarity	NPC314535
0.8407	Intermediate Similarity	NPC304260
0.8407	Intermediate Similarity	NPC292467
0.8407	Intermediate Similarity	NPC30483
0.8407	Intermediate Similarity	NPC32177
0.8407	Intermediate Similarity	NPC469756
0.8407	Intermediate Similarity	NPC5883
0.8407	Intermediate Similarity	NPC329905
0.8407	Intermediate Similarity	NPC55532
0.8407	Intermediate Similarity	NPC44899
0.8407	Intermediate Similarity	NPC236973
0.8407	Intermediate Similarity	NPC29639
0.8407	Intermediate Similarity	NPC470897
0.84	Intermediate Similarity	NPC130840
0.8396	Intermediate Similarity	NPC475521
0.8378	Intermediate Similarity	NPC69576
0.8378	Intermediate Similarity	NPC471633
0.8378	Intermediate Similarity	NPC84949
0.8378	Intermediate Similarity	NPC31354
0.8349	Intermediate Similarity	NPC470867
0.8333	Intermediate Similarity	NPC49032
0.8333	Intermediate Similarity	NPC72260
0.8333	Intermediate Similarity	NPC125324
0.8333	Intermediate Similarity	NPC476513
0.8333	Intermediate Similarity	NPC51172
0.8319	Intermediate Similarity	NPC475403
0.8319	Intermediate Similarity	NPC160888
0.8318	Intermediate Similarity	NPC473199
0.8318	Intermediate Similarity	NPC51719
0.8318	Intermediate Similarity	NPC165405
0.8286	Intermediate Similarity	NPC144486
0.8286	Intermediate Similarity	NPC31346
0.8286	Intermediate Similarity	NPC471112
0.8276	Intermediate Similarity	NPC308262
0.8276	Intermediate Similarity	NPC117445
0.8276	Intermediate Similarity	NPC208193
0.8273	Intermediate Similarity	NPC272242
0.8273	Intermediate Similarity	NPC470311
0.8261	Intermediate Similarity	NPC475590
0.8261	Intermediate Similarity	NPC475419
0.8261	Intermediate Similarity	NPC474908
0.8261	Intermediate Similarity	NPC40749
0.8261	Intermediate Similarity	NPC231518
0.8261	Intermediate Similarity	NPC475219
0.8261	Intermediate Similarity	NPC120390
0.8257	Intermediate Similarity	NPC296761
0.8257	Intermediate Similarity	NPC128133
0.8257	Intermediate Similarity	NPC43976
0.8257	Intermediate Similarity	NPC125361
0.8257	Intermediate Similarity	NPC51925
0.8257	Intermediate Similarity	NPC154085
0.8252	Intermediate Similarity	NPC472989
0.8246	Intermediate Similarity	NPC195560
0.8246	Intermediate Similarity	NPC473633
0.8246	Intermediate Similarity	NPC229962
0.8246	Intermediate Similarity	NPC476085
0.8241	Intermediate Similarity	NPC470166
0.8235	Intermediate Similarity	NPC3359
0.823	Intermediate Similarity	NPC203862
0.823	Intermediate Similarity	NPC290693
0.8218	Intermediate Similarity	NPC219516
0.819	Intermediate Similarity	NPC193893
0.819	Intermediate Similarity	NPC474423
0.819	Intermediate Similarity	NPC43842
0.819	Intermediate Similarity	NPC317019
0.819	Intermediate Similarity	NPC74259
0.8182	Intermediate Similarity	NPC191439
0.8182	Intermediate Similarity	NPC103627
0.8182	Intermediate Similarity	NPC170974
0.8182	Intermediate Similarity	NPC106760
0.8174	Intermediate Similarity	NPC207243
0.8174	Intermediate Similarity	NPC233391
0.8174	Intermediate Similarity	NPC107607
0.8174	Intermediate Similarity	NPC50689
0.8174	Intermediate Similarity	NPC198325
0.8165	Intermediate Similarity	NPC38217
0.8165	Intermediate Similarity	NPC472988
0.8158	Intermediate Similarity	NPC218093
0.8131	Intermediate Similarity	NPC473523
0.8131	Intermediate Similarity	NPC213190
0.812	Intermediate Similarity	NPC106589
0.812	Intermediate Similarity	NPC202261
0.812	Intermediate Similarity	NPC295133
0.812	Intermediate Similarity	NPC257207
0.8119	Intermediate Similarity	NPC219937
0.8119	Intermediate Similarity	NPC123252
0.8119	Intermediate Similarity	NPC194485
0.8119	Intermediate Similarity	NPC53890
0.8113	Intermediate Similarity	NPC475574
0.8113	Intermediate Similarity	NPC176406
0.8108	Intermediate Similarity	NPC13190
0.8108	Intermediate Similarity	NPC114188
0.8108	Intermediate Similarity	NPC65167
0.8095	Intermediate Similarity	NPC157739
0.8091	Intermediate Similarity	NPC240125
0.8091	Intermediate Similarity	NPC473318
0.8091	Intermediate Similarity	NPC473328
0.8091	Intermediate Similarity	NPC28844
0.8091	Intermediate Similarity	NPC91583
0.8091	Intermediate Similarity	NPC474573
0.8087	Intermediate Similarity	NPC291820
0.8087	Intermediate Similarity	NPC81222
0.8077	Intermediate Similarity	NPC156377
0.8073	Intermediate Similarity	NPC122816
0.8073	Intermediate Similarity	NPC226642
0.8073	Intermediate Similarity	NPC471205
0.8073	Intermediate Similarity	NPC234160
0.807	Intermediate Similarity	NPC20979
0.807	Intermediate Similarity	NPC476690
0.807	Intermediate Similarity	NPC100048
0.8058	Intermediate Similarity	NPC477224
0.8058	Intermediate Similarity	NPC113500
0.8058	Intermediate Similarity	NPC3538
0.8056	Intermediate Similarity	NPC85593
0.8056	Intermediate Similarity	NPC473543
0.8056	Intermediate Similarity	NPC31430
0.8056	Intermediate Similarity	NPC475365
0.8037	Intermediate Similarity	NPC475344
0.8037	Intermediate Similarity	NPC476471
0.8037	Intermediate Similarity	NPC470053
0.8036	Intermediate Similarity	NPC473567
0.8036	Intermediate Similarity	NPC475354
0.8036	Intermediate Similarity	NPC112274
0.8036	Intermediate Similarity	NPC231797
0.8036	Intermediate Similarity	NPC216595
0.8036	Intermediate Similarity	NPC243572
0.8036	Intermediate Similarity	NPC473125
0.8034	Intermediate Similarity	NPC115349
0.8019	Intermediate Similarity	NPC471247
0.8019	Intermediate Similarity	NPC91497
0.8018	Intermediate Similarity	NPC65155
0.8017	Intermediate Similarity	NPC257610
0.8017	Intermediate Similarity	NPC475358
0.8017	Intermediate Similarity	NPC473566
0.8	Intermediate Similarity	NPC88744
0.8	Intermediate Similarity	NPC473555
0.8	Intermediate Similarity	NPC471770
0.8	Intermediate Similarity	NPC76486
0.8	Intermediate Similarity	NPC10366
0.8	Intermediate Similarity	NPC475634
0.8	Intermediate Similarity	NPC224414
0.8	Intermediate Similarity	NPC278939
0.7982	Intermediate Similarity	NPC63609
0.7982	Intermediate Similarity	NPC26798

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 NPC473517 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	262
0.1-0.2	2526
0.2-0.3	4110
0.3-0.4	1498
0.4-0.5	371
0.5-0.6	259
0.6-0.7	102
0.7-0.8	10
0.8-0.85	9
0.85-0.9	3
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8739	High Similarity	NPD7516	Approved
0.8649	High Similarity	NPD7328	Approved
0.8649	High Similarity	NPD7327	Approved
0.8421	Intermediate Similarity	NPD8378	Approved
0.8421	Intermediate Similarity	NPD8335	Approved
0.8421	Intermediate Similarity	NPD8296	Approved
0.8421	Intermediate Similarity	NPD8380	Approved
0.8421	Intermediate Similarity	NPD8379	Approved
0.8333	Intermediate Similarity	NPD8294	Approved
0.8333	Intermediate Similarity	NPD8377	Approved
0.8261	Intermediate Similarity	NPD8033	Approved
0.8125	Intermediate Similarity	NPD8133	Approved
0.7833	Intermediate Similarity	NPD7507	Approved
0.7787	Intermediate Similarity	NPD7319	Approved
0.7647	Intermediate Similarity	NPD7503	Approved
0.7453	Intermediate Similarity	NPD8171	Discontinued
0.73	Intermediate Similarity	NPD6928	Phase 2
0.728	Intermediate Similarity	NPD7736	Approved
0.7273	Intermediate Similarity	NPD7638	Approved
0.7207	Intermediate Similarity	NPD7639	Approved
0.7207	Intermediate Similarity	NPD7640	Approved
0.7196	Intermediate Similarity	NPD8034	Phase 2
0.7196	Intermediate Similarity	NPD8035	Phase 2
0.7105	Intermediate Similarity	NPD8170	Clinical (unspecified phase)
0.7069	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD8293	Discontinued
0.704	Intermediate Similarity	NPD7492	Approved
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
0.6983	Remote Similarity	NPD6412	Phase 2
0.6949	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6929	Remote Similarity	NPD7078	Approved
0.6923	Remote Similarity	NPD6686	Approved
0.688	Remote Similarity	NPD6370	Approved
0.6864	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6833	Remote Similarity	NPD6882	Approved
0.6833	Remote Similarity	NPD8297	Approved
0.68	Remote Similarity	NPD6016	Approved
0.68	Remote Similarity	NPD6015	Approved
0.6792	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6783	Remote Similarity	NPD7632	Discontinued
0.6763	Remote Similarity	NPD7625	Phase 1
0.6748	Remote Similarity	NPD6009	Approved
0.6746	Remote Similarity	NPD5988	Approved
0.6697	Remote Similarity	NPD6051	Approved
0.6695	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6639	Remote Similarity	NPD7320	Approved
0.6635	Remote Similarity	NPD7525	Registered
0.6613	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.661	Remote Similarity	NPD6675	Approved
0.661	Remote Similarity	NPD5739	Approved
0.661	Remote Similarity	NPD6008	Approved
0.661	Remote Similarity	NPD6402	Approved
0.661	Remote Similarity	NPD7128	Approved
0.6587	Remote Similarity	NPD6319	Approved
0.6583	Remote Similarity	NPD6372	Approved
0.6583	Remote Similarity	NPD6373	Approved
0.6562	Remote Similarity	NPD8328	Phase 3
0.6552	Remote Similarity	NPD5344	Discontinued
0.6549	Remote Similarity	NPD7991	Discontinued
0.6535	Remote Similarity	NPD6921	Approved
0.6514	Remote Similarity	NPD7524	Approved
0.6504	Remote Similarity	NPD4632	Approved
0.65	Remote Similarity	NPD6899	Approved
0.65	Remote Similarity	NPD6881	Approved
0.6489	Remote Similarity	NPD6033	Approved
0.648	Remote Similarity	NPD7115	Discovery
0.6475	Remote Similarity	NPD6650	Approved
0.6475	Remote Similarity	NPD6649	Approved
0.6475	Remote Similarity	NPD8130	Phase 1
0.6466	Remote Similarity	NPD6648	Approved
0.6434	Remote Similarity	NPD6067	Discontinued
0.6417	Remote Similarity	NPD5697	Approved
0.6417	Remote Similarity	NPD5701	Approved
0.641	Remote Similarity	NPD1700	Approved
0.6406	Remote Similarity	NPD8516	Approved
0.6406	Remote Similarity	NPD8515	Approved
0.6406	Remote Similarity	NPD8513	Phase 3
0.6406	Remote Similarity	NPD8517	Approved
0.6393	Remote Similarity	NPD7290	Approved
0.6393	Remote Similarity	NPD7102	Approved
0.6393	Remote Similarity	NPD6883	Approved
0.6389	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6379	Remote Similarity	NPD4225	Approved
0.6372	Remote Similarity	NPD6399	Phase 3
0.6341	Remote Similarity	NPD6847	Approved
0.6341	Remote Similarity	NPD6869	Approved
0.6341	Remote Similarity	NPD6617	Approved
0.6341	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD7748	Approved
0.6311	Remote Similarity	NPD6012	Approved
0.6311	Remote Similarity	NPD6013	Approved
0.6311	Remote Similarity	NPD6014	Approved
0.6308	Remote Similarity	NPD7604	Phase 2
0.6296	Remote Similarity	NPD8449	Approved
0.6296	Remote Similarity	NPD6695	Phase 3
0.6293	Remote Similarity	NPD6083	Phase 2
0.6293	Remote Similarity	NPD6084	Phase 2
0.6293	Remote Similarity	NPD7902	Approved
0.629	Remote Similarity	NPD6053	Discontinued
0.6286	Remote Similarity	NPD6118	Approved
0.6286	Remote Similarity	NPD6114	Approved
0.6286	Remote Similarity	NPD6115	Approved
0.6286	Remote Similarity	NPD6697	Approved
0.6279	Remote Similarity	NPD5983	Phase 2
0.6271	Remote Similarity	NPD4159	Approved
0.6261	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.625	Remote Similarity	NPD8450	Suspended
0.6238	Remote Similarity	NPD7532	Clinical (unspecified phase)
0.623	Remote Similarity	NPD6011	Approved
0.6216	Remote Similarity	NPD7750	Discontinued
0.6212	Remote Similarity	NPD6336	Discontinued
0.621	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.619	Remote Similarity	NPD6116	Phase 1
0.6161	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD4755	Approved
0.6148	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6147	Remote Similarity	NPD4788	Approved
0.6147	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.6147	Remote Similarity	NPD3669	Approved
0.614	Remote Similarity	NPD7637	Suspended
0.6139	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.6121	Remote Similarity	NPD5695	Phase 3
0.6102	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6102	Remote Similarity	NPD5696	Approved
0.6095	Remote Similarity	NPD6117	Approved
0.6087	Remote Similarity	NPD4202	Approved
0.6083	Remote Similarity	NPD5211	Phase 2
0.6075	Remote Similarity	NPD7645	Phase 2
0.6071	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6053	Remote Similarity	NPD3168	Discontinued
0.605	Remote Similarity	NPD5286	Approved
0.605	Remote Similarity	NPD4700	Approved
0.605	Remote Similarity	NPD5285	Approved
0.605	Remote Similarity	NPD4696	Approved
0.6045	Remote Similarity	NPD8074	Phase 3
0.6034	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6034	Remote Similarity	NPD7900	Approved
0.6029	Remote Similarity	NPD5956	Approved
0.6019	Remote Similarity	NPD6931	Approved
0.6019	Remote Similarity	NPD6930	Phase 2
0.6018	Remote Similarity	NPD6903	Approved
0.6016	Remote Similarity	NPD6274	Approved
0.6016	Remote Similarity	NPD6940	Discontinued
0.6	Remote Similarity	NPD4634	Approved
0.6	Remote Similarity	NPD7100	Approved
0.6	Remote Similarity	NPD7101	Approved
0.6	Remote Similarity	NPD3702	Approved
0.6	Remote Similarity	NPD7515	Phase 2
0.6	Remote Similarity	NPD5693	Phase 1
0.5984	Remote Similarity	NPD5141	Approved
0.5982	Remote Similarity	NPD5330	Approved
0.5982	Remote Similarity	NPD6684	Approved
0.5982	Remote Similarity	NPD6409	Approved
0.5982	Remote Similarity	NPD7521	Approved
0.5982	Remote Similarity	NPD7146	Approved
0.5982	Remote Similarity	NPD7334	Approved
0.595	Remote Similarity	NPD5225	Approved
0.595	Remote Similarity	NPD5226	Approved
0.595	Remote Similarity	NPD4633	Approved
0.595	Remote Similarity	NPD5224	Approved
0.5943	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.5942	Remote Similarity	NPD8338	Approved
0.5935	Remote Similarity	NPD4767	Approved
0.5935	Remote Similarity	NPD4768	Approved
0.5926	Remote Similarity	NPD6929	Approved
0.5923	Remote Similarity	NPD6335	Approved
0.5909	Remote Similarity	NPD6908	Approved
0.5909	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.5909	Remote Similarity	NPD6909	Approved
0.5905	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.5902	Remote Similarity	NPD5174	Approved
0.5902	Remote Similarity	NPD5175	Approved
0.5901	Remote Similarity	NPD7799	Discontinued
0.5897	Remote Similarity	NPD6001	Approved
0.5893	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.5868	Remote Similarity	NPD5223	Approved
0.5865	Remote Similarity	NPD4243	Approved
0.5862	Remote Similarity	NPD7087	Discontinued
0.5849	Remote Similarity	NPD7339	Approved
0.5849	Remote Similarity	NPD6942	Approved
0.5846	Remote Similarity	NPD6317	Approved
0.5841	Remote Similarity	NPD6098	Approved
0.584	Remote Similarity	NPD4730	Approved
0.584	Remote Similarity	NPD4729	Approved
0.5826	Remote Similarity	NPD6673	Approved
0.5826	Remote Similarity	NPD6080	Approved
0.5826	Remote Similarity	NPD5328	Approved
0.5826	Remote Similarity	NPD4753	Phase 2
0.5826	Remote Similarity	NPD6904	Approved
0.5804	Remote Similarity	NPD4786	Approved
0.5802	Remote Similarity	NPD6313	Approved
0.5802	Remote Similarity	NPD6314	Approved
0.5789	Remote Similarity	NPD4251	Approved
0.5789	Remote Similarity	NPD4250	Approved
0.578	Remote Similarity	NPD4195	Approved
0.5776	Remote Similarity	NPD7838	Discovery
0.5776	Remote Similarity	NPD46	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