NPASS Compound

Structure

NPC473158 OpenBabel07101718322D 35 39 0 0 1 0 0 0 0 0999 V2000 4.2139 0.2462 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1710 -0.9431 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7707 -1.0787 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2463 -1.9024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8238 -2.3780 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8238 1.4268 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8238 0.4756 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8238 -1.4268 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.9024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4713 -0.4756 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4713 -3.3293 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6476 -2.8537 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6476 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4713 -0.4756 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.9512 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6476 2.8537 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8238 -0.4756 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6476 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.4713 -1.4268 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8238 -1.4268 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.2951 -2.8537 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8238 1.4268 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.2951 0.9512 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.4713 1.4268 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.2951 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2951 -1.9024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6476 -1.9024 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8238 -0.4756 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6476 0.9512 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.4713 3.3293 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.1189 -3.3293 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8238 2.3780 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.1189 1.4268 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.4713 2.3780 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 25 1 0 0 0 0 2 25 1 0 0 0 0 3 26 1 0 0 0 0 4 26 1 0 0 0 0 6 28 1 0 0 0 0 8 9 1 0 0 0 0 8 17 2 0 0 0 0 9 20 1 0 0 0 0 10 13 1 0 0 0 0 10 19 1 0 0 0 0 11 12 2 0 0 0 0 11 21 1 0 0 0 0 12 27 1 0 0 0 0 13 28 1 0 0 0 0 14 18 1 0 0 0 0 14 25 1 0 0 0 0 15 22 1 0 0 0 0 15 29 1 0 0 0 0 16 31 1 0 0 0 0 17 18 1 0 0 0 0 17 29 1 0 0 0 0 18 30 1 1 0 0 0 19 26 1 0 0 0 0 19 27 1 6 0 0 0 20 27 1 6 0 0 0 20 28 1 0 0 0 0 21 26 1 0 0 0 0 21 32 2 0 0 0 0 22 30 1 1 0 0 0 22 33 1 0 0 0 0 23 24 1 0 0 0 0 23 25 1 0 0 0 0 23 34 1 6 0 0 0 24 30 1 1 0 0 0 24 35 1 0 0 0 0 27 5 1 6 0 0 0 28 29 1 1 0 0 0 29 7 1 1 0 0 0 30 16 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	486.33
Volume:	520.695
LogP:	3.865
LogD:	3.443
LogS:	-4.28
# Rotatable Bonds:	1
TPSA:	97.99
# H-Bond Aceptor:	5
# H-Bond Donor:	4
# Rings:	5
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.42
Synthetic Accessibility Score:	5.238
Fsp3:	0.833
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:	-5.179
MDCK Permeability:	2.509317891963292e-05
Pgp-inhibitor:	0.609
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.011
20% Bioavailability (F20%):	0.004
30% Bioavailability (F30%):	0.471

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.133
Plasma Protein Binding (PPB):	88.3733901977539%
Volume Distribution (VD):	0.906
Pgp-substrate:	9.36342716217041%

ADMET: Metabolism

CYP1A2-inhibitor:	0.009
CYP1A2-substrate:	0.114
CYP2C19-inhibitor:	0.01
CYP2C19-substrate:	0.825
CYP2C9-inhibitor:	0.06
CYP2C9-substrate:	0.08
CYP2D6-inhibitor:	0.007
CYP2D6-substrate:	0.059
CYP3A4-inhibitor:	0.65
CYP3A4-substrate:	0.443

ADMET: Excretion

Clearance (CL):	2.864
Half-life (T1/2):	0.432

ADMET: Toxicity

hERG Blockers:	0.581
Human Hepatotoxicity (H-HT):	0.254
Drug-inuced Liver Injury (DILI):	0.028
AMES Toxicity:	0.035
Rat Oral Acute Toxicity:	0.978
Maximum Recommended Daily Dose:	0.998
Skin Sensitization:	0.534
Carcinogencity:	0.049
Eye Corrosion:	0.004
Eye Irritation:	0.023
Respiratory Toxicity:	0.978

Download Data

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

Natural Product: NPC473158

Natural Product ID:	NPC473158
*Common Name:**	YZBJCTMVHOPEJZ-XZVLIDTCSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	YZBJCTMVHOPEJZ-XZVLIDTCSA-N
Standard InCHI:	InChI=1S/C30H46O5/c1-25(2)14-18-17-8-9-20-27(5)12-11-21(32)26(3,4)19(27)10-13-28(20,6)29(17,7)15-22(33)30(18,16-31)24(35)23(25)34/h8,11-12,18-20,22-24,31,33-35H,9-10,13-16H2,1-7H3/t18-,19-,20+,22+,23-,24-,27-,28+,29+,30-/m0/s1
SMILES:	OC[C@]12[C@H](O)C[C@@]3(C(=CC[C@H]4[C@@]3(C)CC[C@@H]3[C@]4(C)C=CC(=O)C3(C)C)[C@@H]2CC([C@H]([C@@H]1O)O)(C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3632762
PubChem CID:	n.a.
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
NPO33464	cyrilla racemiflora	Species	Cyrillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26422131]

☑ 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
NPT139	Cell Line	HT-29	Homo sapiens	IC50	>	10000.0	nM	PMID[459760]

☑ 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 NPC473158 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	215
0.1-0.2	1259
0.2-0.3	4514
0.3-0.4	10610
0.4-0.5	12455
0.5-0.6	6126
0.6-0.7	5090
0.7-0.8	2098
0.8-0.85	267
0.85-0.9	59
0.9-0.95	3
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9032	High Similarity	NPC32118
0.8925	High Similarity	NPC282395
0.8925	High Similarity	NPC23170
0.8925	High Similarity	NPC263548
0.8925	High Similarity	NPC145667
0.8925	High Similarity	NPC88116
0.8925	High Similarity	NPC32407
0.8925	High Similarity	NPC20235
0.8925	High Similarity	NPC299996
0.8925	High Similarity	NPC231063
0.8817	High Similarity	NPC474806
0.8817	High Similarity	NPC133579
0.8791	High Similarity	NPC158778
0.8778	High Similarity	NPC213412
0.8737	High Similarity	NPC173744
0.8737	High Similarity	NPC88847
0.8737	High Similarity	NPC307282
0.8737	High Similarity	NPC204961
0.8737	High Similarity	NPC305464
0.8737	High Similarity	NPC201657
0.8737	High Similarity	NPC25848
0.8737	High Similarity	NPC73004
0.8737	High Similarity	NPC19376
0.871	High Similarity	NPC235884
0.871	High Similarity	NPC52021
0.871	High Similarity	NPC233455
0.871	High Similarity	NPC306541
0.871	High Similarity	NPC472149
0.871	High Similarity	NPC65120
0.871	High Similarity	NPC84319
0.871	High Similarity	NPC145067
0.871	High Similarity	NPC4036
0.871	High Similarity	NPC71074
0.871	High Similarity	NPC25299
0.871	High Similarity	NPC155304
0.871	High Similarity	NPC158030
0.871	High Similarity	NPC300351
0.871	High Similarity	NPC272746
0.8667	High Similarity	NPC133954
0.8646	High Similarity	NPC247139
0.8646	High Similarity	NPC261935
0.8646	High Similarity	NPC106112
0.8646	High Similarity	NPC9613
0.8632	High Similarity	NPC198245
0.8632	High Similarity	NPC96916
0.8632	High Similarity	NPC148523
0.8632	High Similarity	NPC139570
0.8617	High Similarity	NPC214756
0.8617	High Similarity	NPC295643
0.8617	High Similarity	NPC275809
0.8617	High Similarity	NPC136313
0.8617	High Similarity	NPC74855
0.8617	High Similarity	NPC272075
0.8617	High Similarity	NPC307335
0.8602	High Similarity	NPC130278
0.8602	High Similarity	NPC49320
0.8602	High Similarity	NPC85173
0.8587	High Similarity	NPC206060
0.8587	High Similarity	NPC472802
0.8571	High Similarity	NPC158393
0.8571	High Similarity	NPC475862
0.8571	High Similarity	NPC74363
0.8557	High Similarity	NPC111214
0.8557	High Similarity	NPC271614
0.8557	High Similarity	NPC29765
0.8542	High Similarity	NPC98874
0.8542	High Similarity	NPC259733
0.8542	High Similarity	NPC158371
0.8542	High Similarity	NPC207922
0.8526	High Similarity	NPC471207
0.8526	High Similarity	NPC188102
0.8526	High Similarity	NPC80365
0.8511	High Similarity	NPC105189
0.8495	Intermediate Similarity	NPC121798
0.8495	Intermediate Similarity	NPC130520
0.8495	Intermediate Similarity	NPC290972
0.8495	Intermediate Similarity	NPC61543
0.8495	Intermediate Similarity	NPC263393
0.8495	Intermediate Similarity	NPC64872
0.8495	Intermediate Similarity	NPC293048
0.8495	Intermediate Similarity	NPC225585
0.8495	Intermediate Similarity	NPC250592
0.8495	Intermediate Similarity	NPC127689
0.8495	Intermediate Similarity	NPC59263
0.8495	Intermediate Similarity	NPC77263
0.8495	Intermediate Similarity	NPC25906
0.8495	Intermediate Similarity	NPC270768
0.8495	Intermediate Similarity	NPC234346
0.8478	Intermediate Similarity	NPC73064
0.8469	Intermediate Similarity	NPC35239
0.8454	Intermediate Similarity	NPC259788
0.8454	Intermediate Similarity	NPC203343
0.8454	Intermediate Similarity	NPC312075
0.8454	Intermediate Similarity	NPC43686
0.8454	Intermediate Similarity	NPC255589
0.8444	Intermediate Similarity	NPC159168
0.8444	Intermediate Similarity	NPC253402
0.8438	Intermediate Similarity	NPC473170
0.8421	Intermediate Similarity	NPC211230
0.8421	Intermediate Similarity	NPC229281
0.8421	Intermediate Similarity	NPC118490
0.8404	Intermediate Similarity	NPC120968
0.8404	Intermediate Similarity	NPC290614
0.8404	Intermediate Similarity	NPC291028
0.8404	Intermediate Similarity	NPC470589
0.8404	Intermediate Similarity	NPC126369
0.8404	Intermediate Similarity	NPC477872
0.8404	Intermediate Similarity	NPC193750
0.8404	Intermediate Similarity	NPC7260
0.8404	Intermediate Similarity	NPC111110
0.8404	Intermediate Similarity	NPC273621
0.8404	Intermediate Similarity	NPC210037
0.8404	Intermediate Similarity	NPC227467
0.8404	Intermediate Similarity	NPC18872
0.8387	Intermediate Similarity	NPC230387
0.8387	Intermediate Similarity	NPC182797
0.8387	Intermediate Similarity	NPC474925
0.8387	Intermediate Similarity	NPC52169
0.8384	Intermediate Similarity	NPC256247
0.837	Intermediate Similarity	NPC95594
0.837	Intermediate Similarity	NPC179591
0.837	Intermediate Similarity	NPC235341
0.837	Intermediate Similarity	NPC477579
0.8352	Intermediate Similarity	NPC180834
0.8352	Intermediate Similarity	NPC238992
0.8351	Intermediate Similarity	NPC230151
0.8351	Intermediate Similarity	NPC61369
0.8351	Intermediate Similarity	NPC469545
0.8351	Intermediate Similarity	NPC167193
0.8351	Intermediate Similarity	NPC5532
0.8351	Intermediate Similarity	NPC472806
0.8333	Intermediate Similarity	NPC472977
0.8333	Intermediate Similarity	NPC6818
0.8333	Intermediate Similarity	NPC87095
0.8333	Intermediate Similarity	NPC114159
0.8333	Intermediate Similarity	NPC74751
0.8333	Intermediate Similarity	NPC47763
0.8333	Intermediate Similarity	NPC191412
0.8333	Intermediate Similarity	NPC474328
0.8333	Intermediate Similarity	NPC472976
0.8316	Intermediate Similarity	NPC288833
0.8316	Intermediate Similarity	NPC38754
0.8316	Intermediate Similarity	NPC235704
0.8316	Intermediate Similarity	NPC228784
0.8316	Intermediate Similarity	NPC301244
0.8316	Intermediate Similarity	NPC187722
0.8316	Intermediate Similarity	NPC324341
0.8316	Intermediate Similarity	NPC473167
0.8316	Intermediate Similarity	NPC155120
0.8316	Intermediate Similarity	NPC282616
0.8316	Intermediate Similarity	NPC472978
0.8316	Intermediate Similarity	NPC474525
0.8316	Intermediate Similarity	NPC966
0.8316	Intermediate Similarity	NPC6255
0.8316	Intermediate Similarity	NPC471588
0.8298	Intermediate Similarity	NPC198664
0.8298	Intermediate Similarity	NPC69627
0.8298	Intermediate Similarity	NPC472983
0.8298	Intermediate Similarity	NPC143232
0.8298	Intermediate Similarity	NPC274330
0.8298	Intermediate Similarity	NPC31985
0.8298	Intermediate Similarity	NPC1015
0.828	Intermediate Similarity	NPC242468
0.828	Intermediate Similarity	NPC472324
0.828	Intermediate Similarity	NPC51700
0.828	Intermediate Similarity	NPC130577
0.828	Intermediate Similarity	NPC93778
0.828	Intermediate Similarity	NPC88716
0.828	Intermediate Similarity	NPC68160
0.828	Intermediate Similarity	NPC142415
0.828	Intermediate Similarity	NPC102683
0.828	Intermediate Similarity	NPC293564
0.828	Intermediate Similarity	NPC18064
0.828	Intermediate Similarity	NPC171203
0.828	Intermediate Similarity	NPC71507
0.828	Intermediate Similarity	NPC307426
0.828	Intermediate Similarity	NPC98442
0.8265	Intermediate Similarity	NPC89225
0.8265	Intermediate Similarity	NPC473456
0.8265	Intermediate Similarity	NPC26413
0.8261	Intermediate Similarity	NPC474537
0.8261	Intermediate Similarity	NPC470574
0.8247	Intermediate Similarity	NPC83693
0.8229	Intermediate Similarity	NPC202728
0.8229	Intermediate Similarity	NPC158059
0.8229	Intermediate Similarity	NPC118519
0.8229	Intermediate Similarity	NPC475255
0.8229	Intermediate Similarity	NPC86368
0.8229	Intermediate Similarity	NPC109305
0.8222	Intermediate Similarity	NPC473217
0.8222	Intermediate Similarity	NPC3915
0.8218	Intermediate Similarity	NPC239716
0.8211	Intermediate Similarity	NPC472325
0.8211	Intermediate Similarity	NPC86372
0.8211	Intermediate Similarity	NPC191684
0.8211	Intermediate Similarity	NPC46441
0.8211	Intermediate Similarity	NPC126993
0.8211	Intermediate Similarity	NPC172361
0.82	Intermediate Similarity	NPC233012
0.82	Intermediate Similarity	NPC54909

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 NPC473158 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	196
0.1-0.2	1623
0.2-0.3	3771
0.3-0.4	2400
0.4-0.5	728
0.5-0.6	182
0.6-0.7	140
0.7-0.8	107
0.8-0.85	2
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.871	High Similarity	NPD7515	Phase 2
0.8333	Intermediate Similarity	NPD7748	Approved
0.8316	Intermediate Similarity	NPD6079	Approved
0.8265	Intermediate Similarity	NPD7902	Approved
0.8172	Intermediate Similarity	NPD3618	Phase 1
0.8105	Intermediate Similarity	NPD5328	Approved
0.81	Intermediate Similarity	NPD5286	Approved
0.81	Intermediate Similarity	NPD5285	Approved
0.81	Intermediate Similarity	NPD4696	Approved
0.798	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.798	Intermediate Similarity	NPD5222	Approved
0.798	Intermediate Similarity	NPD5221	Approved
0.7959	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7959	Intermediate Similarity	NPD7900	Approved
0.7941	Intermediate Similarity	NPD5226	Approved
0.7941	Intermediate Similarity	NPD4633	Approved
0.7941	Intermediate Similarity	NPD5211	Phase 2
0.7941	Intermediate Similarity	NPD5224	Approved
0.7941	Intermediate Similarity	NPD5225	Approved
0.79	Intermediate Similarity	NPD5173	Approved
0.79	Intermediate Similarity	NPD4755	Approved
0.7864	Intermediate Similarity	NPD5175	Approved
0.7864	Intermediate Similarity	NPD5174	Approved
0.7857	Intermediate Similarity	NPD4202	Approved
0.7843	Intermediate Similarity	NPD5223	Approved
0.7802	Intermediate Similarity	NPD7645	Phase 2
0.7788	Intermediate Similarity	NPD5141	Approved
0.7766	Intermediate Similarity	NPD3133	Approved
0.7766	Intermediate Similarity	NPD3666	Approved
0.7766	Intermediate Similarity	NPD4786	Approved
0.7766	Intermediate Similarity	NPD3665	Phase 1
0.7757	Intermediate Similarity	NPD4634	Approved
0.7745	Intermediate Similarity	NPD4700	Approved
0.7742	Intermediate Similarity	NPD3667	Approved
0.7736	Intermediate Similarity	NPD6899	Approved
0.7736	Intermediate Similarity	NPD6881	Approved
0.7642	Intermediate Similarity	NPD5697	Approved
0.7624	Intermediate Similarity	NPD4697	Phase 3
0.7615	Intermediate Similarity	NPD8297	Approved
0.7593	Intermediate Similarity	NPD7290	Approved
0.7593	Intermediate Similarity	NPD7102	Approved
0.7593	Intermediate Similarity	NPD6883	Approved
0.757	Intermediate Similarity	NPD4730	Approved
0.757	Intermediate Similarity	NPD4729	Approved
0.7551	Intermediate Similarity	NPD4753	Phase 2
0.7551	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.7547	Intermediate Similarity	NPD5739	Approved
0.7547	Intermediate Similarity	NPD6675	Approved
0.7547	Intermediate Similarity	NPD6402	Approved
0.7547	Intermediate Similarity	NPD7128	Approved
0.7527	Intermediate Similarity	NPD4695	Discontinued
0.7525	Intermediate Similarity	NPD5210	Approved
0.7525	Intermediate Similarity	NPD4629	Approved
0.7523	Intermediate Similarity	NPD8130	Phase 1
0.7523	Intermediate Similarity	NPD6617	Approved
0.7523	Intermediate Similarity	NPD6650	Approved
0.7523	Intermediate Similarity	NPD6869	Approved
0.7523	Intermediate Similarity	NPD6649	Approved
0.7523	Intermediate Similarity	NPD6847	Approved
0.75	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6013	Approved
0.75	Intermediate Similarity	NPD6012	Approved
0.75	Intermediate Similarity	NPD6014	Approved
0.75	Intermediate Similarity	NPD7115	Discovery
0.7477	Intermediate Similarity	NPD6412	Phase 2
0.7455	Intermediate Similarity	NPD6882	Approved
0.7431	Intermediate Similarity	NPD5248	Approved
0.7431	Intermediate Similarity	NPD5250	Approved
0.7431	Intermediate Similarity	NPD5251	Approved
0.7431	Intermediate Similarity	NPD5247	Approved
0.7431	Intermediate Similarity	NPD5249	Phase 3
0.7423	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7423	Intermediate Similarity	NPD5279	Phase 3
0.7407	Intermediate Similarity	NPD5128	Approved
0.7407	Intermediate Similarity	NPD6011	Approved
0.7407	Intermediate Similarity	NPD7320	Approved
0.7387	Intermediate Similarity	NPD4632	Approved
0.7383	Intermediate Similarity	NPD4767	Approved
0.7383	Intermediate Similarity	NPD4768	Approved
0.7364	Intermediate Similarity	NPD5215	Approved
0.7364	Intermediate Similarity	NPD5216	Approved
0.7364	Intermediate Similarity	NPD5217	Approved
0.7358	Intermediate Similarity	NPD4754	Approved
0.7347	Intermediate Similarity	NPD3573	Approved
0.734	Intermediate Similarity	NPD7525	Registered
0.7339	Intermediate Similarity	NPD6373	Approved
0.7339	Intermediate Similarity	NPD6372	Approved
0.7327	Intermediate Similarity	NPD6399	Phase 3
0.732	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7315	Intermediate Similarity	NPD5701	Approved
0.7282	Intermediate Similarity	NPD7614	Phase 1
0.7273	Intermediate Similarity	NPD5169	Approved
0.7273	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD5134	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD5135	Approved
0.7265	Intermediate Similarity	NPD8328	Phase 3
0.7248	Intermediate Similarity	NPD5168	Approved
0.7245	Intermediate Similarity	NPD5690	Phase 2
0.7216	Intermediate Similarity	NPD3668	Phase 3
0.7212	Intermediate Similarity	NPD6083	Phase 2
0.7212	Intermediate Similarity	NPD6084	Phase 2
0.7207	Intermediate Similarity	NPD5127	Approved
0.7188	Intermediate Similarity	NPD4223	Phase 3
0.7188	Intermediate Similarity	NPD4221	Approved
0.7158	Intermediate Similarity	NPD8259	Clinical (unspecified phase)
0.7155	Intermediate Similarity	NPD6319	Approved
0.7155	Intermediate Similarity	NPD6054	Approved
0.7143	Intermediate Similarity	NPD7638	Approved
0.7143	Intermediate Similarity	NPD5329	Approved
0.7113	Intermediate Similarity	NPD4788	Approved
0.7075	Intermediate Similarity	NPD7639	Approved
0.7075	Intermediate Similarity	NPD7640	Approved
0.7071	Intermediate Similarity	NPD7146	Approved
0.7071	Intermediate Similarity	NPD6409	Approved
0.7071	Intermediate Similarity	NPD6684	Approved
0.7071	Intermediate Similarity	NPD5330	Approved
0.7071	Intermediate Similarity	NPD4623	Approved
0.7071	Intermediate Similarity	NPD4519	Discontinued
0.7071	Intermediate Similarity	NPD7521	Approved
0.7071	Intermediate Similarity	NPD7334	Approved
0.7069	Intermediate Similarity	NPD7100	Approved
0.7069	Intermediate Similarity	NPD7101	Approved
0.7059	Intermediate Similarity	NPD5284	Approved
0.7059	Intermediate Similarity	NPD8035	Phase 2
0.7059	Intermediate Similarity	NPD6411	Approved
0.7059	Intermediate Similarity	NPD8034	Phase 2
0.7059	Intermediate Similarity	NPD5281	Approved
0.7054	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7043	Intermediate Similarity	NPD6009	Approved
0.7041	Intermediate Similarity	NPD4197	Approved
0.7034	Intermediate Similarity	NPD6370	Approved
0.7027	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD7736	Approved
0.7019	Intermediate Similarity	NPD5695	Phase 3
0.7018	Intermediate Similarity	NPD5167	Approved
0.6983	Remote Similarity	NPD6335	Approved
0.6981	Remote Similarity	NPD4225	Approved
0.6957	Remote Similarity	NPD6274	Approved
0.6957	Remote Similarity	NPD6868	Approved
0.6952	Remote Similarity	NPD7732	Phase 3
0.6949	Remote Similarity	NPD6015	Approved
0.6949	Remote Similarity	NPD6016	Approved
0.6947	Remote Similarity	NPD3617	Approved
0.6937	Remote Similarity	NPD6686	Approved
0.6931	Remote Similarity	NPD6672	Approved
0.6931	Remote Similarity	NPD6903	Approved
0.6931	Remote Similarity	NPD5737	Approved
0.6917	Remote Similarity	NPD7492	Approved
0.69	Remote Similarity	NPD4689	Approved
0.69	Remote Similarity	NPD5280	Approved
0.69	Remote Similarity	NPD4694	Approved
0.69	Remote Similarity	NPD4693	Phase 3
0.69	Remote Similarity	NPD5205	Approved
0.69	Remote Similarity	NPD4688	Approved
0.69	Remote Similarity	NPD4138	Approved
0.69	Remote Similarity	NPD4690	Approved
0.6897	Remote Similarity	NPD6317	Approved
0.6891	Remote Similarity	NPD5988	Approved
0.6875	Remote Similarity	NPD4195	Approved
0.6864	Remote Similarity	NPD6059	Approved
0.6863	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6863	Remote Similarity	NPD6101	Approved
0.686	Remote Similarity	NPD6616	Approved
0.6838	Remote Similarity	NPD6313	Approved
0.6838	Remote Similarity	NPD6314	Approved
0.6833	Remote Similarity	NPD7604	Phase 2
0.6822	Remote Similarity	NPD5290	Discontinued
0.6822	Remote Similarity	NPD5696	Approved
0.6809	Remote Similarity	NPD7339	Approved
0.6809	Remote Similarity	NPD6942	Approved
0.6807	Remote Similarity	NPD5983	Phase 2
0.6803	Remote Similarity	NPD7078	Approved
0.6786	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.678	Remote Similarity	NPD4522	Approved
0.6752	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6739	Remote Similarity	NPD4691	Approved
0.6737	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6735	Remote Similarity	NPD8028	Phase 2
0.6721	Remote Similarity	NPD7507	Approved
0.6721	Remote Similarity	NPD6336	Discontinued
0.6702	Remote Similarity	NPD4058	Approved
0.6698	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6908	Approved
0.6667	Remote Similarity	NPD6116	Phase 1
0.6667	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6909	Approved
0.6634	Remote Similarity	NPD1694	Approved
0.663	Remote Similarity	NPD4137	Phase 3
0.663	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.663	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6607	Remote Similarity	NPD6008	Approved
0.6562	Remote Similarity	NPD6117	Approved
0.656	Remote Similarity	NPD7319	Approved
0.6559	Remote Similarity	NPD4747	Approved
0.6557	Remote Similarity	NPD6067	Discontinued
0.6538	Remote Similarity	NPD6904	Approved
0.6538	Remote Similarity	NPD6673	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