NPASS Compound

Structure

NPC169343 OpenBabel07101718282D 36 40 0 0 1 0 0 0 0 0999 V2000 0.8449 -3.4146 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0225 2.3083 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0469 2.3083 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3796 -0.9756 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0225 -4.2595 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6898 -0.9756 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8449 1.4634 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8449 0.4878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6898 -2.9268 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8449 1.4634 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3796 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5347 -0.4878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.9756 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3796 -1.9512 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3796 -2.9268 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5347 -0.4878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6898 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.9512 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6898 -2.9268 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8449 -1.4634 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6898 -1.9512 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8449 -1.4634 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6898 0.9756 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.3796 0.9756 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8449 -0.4878 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.0469 -4.2595 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5347 1.4634 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5347 -1.4634 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5347 -3.4146 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6898 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8449 -0.4878 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 4.2245 1.4634 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5347 -5.1044 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0713 -4.2595 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6898 -1.9512 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 9 1 0 0 0 0 2 27 1 0 0 0 0 3 27 1 0 0 0 0 7 31 1 0 0 0 0 9 36 1 0 0 0 0 10 13 1 0 0 0 0 10 23 1 0 0 0 0 11 12 1 0 0 0 0 11 24 1 0 0 0 0 12 30 1 0 0 0 0 13 32 1 0 0 0 0 14 15 1 0 0 0 0 14 28 1 0 0 0 0 15 29 1 0 0 0 0 16 17 1 0 0 0 0 16 28 1 0 0 0 0 17 31 1 0 0 0 0 18 20 2 0 0 0 0 18 22 1 0 0 0 0 19 21 1 0 0 0 0 19 29 1 0 0 0 0 20 21 1 0 0 0 0 20 31 1 0 0 0 0 21 28 1 6 0 0 0 22 25 1 0 0 0 0 22 36 1 6 0 0 0 23 27 1 0 0 0 0 23 30 1 1 0 0 0 24 27 1 0 0 0 0 24 33 2 0 0 0 0 25 30 1 1 0 0 0 25 32 1 0 0 0 0 26 29 1 0 0 0 0 26 34 2 0 0 0 0 26 35 1 0 0 0 0 28 4 1 1 0 0 0 29 5 1 6 0 0 0 30 6 1 1 0 0 0 31 32 1 1 0 0 0 32 8 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	498.37
Volume:	546.497
LogP:	6.707
LogD:	4.614
LogS:	-4.707
# Rotatable Bonds:	3
TPSA:	63.6
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	5
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.41
Synthetic Accessibility Score:	5.028
Fsp3:	0.875
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-5.499
MDCK Permeability:	1.2537014299596194e-05
Pgp-inhibitor:	0.408
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.041
20% Bioavailability (F20%):	0.063
30% Bioavailability (F30%):	0.99

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.113
Plasma Protein Binding (PPB):	88.1922378540039%
Volume Distribution (VD):	0.69
Pgp-substrate:	5.1067423820495605%

ADMET: Metabolism

CYP1A2-inhibitor:	0.007
CYP1A2-substrate:	0.919
CYP2C19-inhibitor:	0.02
CYP2C19-substrate:	0.904
CYP2C9-inhibitor:	0.149
CYP2C9-substrate:	0.133
CYP2D6-inhibitor:	0.01
CYP2D6-substrate:	0.069
CYP3A4-inhibitor:	0.58
CYP3A4-substrate:	0.597

ADMET: Excretion

Clearance (CL):	2.296
Half-life (T1/2):	0.157

ADMET: Toxicity

hERG Blockers:	0.014
Human Hepatotoxicity (H-HT):	0.308
Drug-inuced Liver Injury (DILI):	0.025
AMES Toxicity:	0.012
Rat Oral Acute Toxicity:	0.609
Maximum Recommended Daily Dose:	0.857
Skin Sensitization:	0.031
Carcinogencity:	0.189
Eye Corrosion:	0.005
Eye Irritation:	0.03
Respiratory Toxicity:	0.976

Download Data

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

Natural Product: NPC169343

Natural Product ID:	NPC169343
*Common Name:**	3-Oxo-11 Alpha-Ethoxyolean-12-Ene-30-Oic Acid
IUPAC Name:	(2S,4aS,6aR,6aS,6bR,8aR,12aS,13R,14bR)-13-ethoxy-2,4a,6a,6b,9,9,12a-heptamethyl-10-oxo-3,4,5,6,6a,7,8,8a,11,12,13,14b-dodecahydro-1H-picene-2-carboxylic acid
Synonyms:
Standard InCHIKey:	KZKWPSFPAWXVEN-GQENXVRPSA-N
Standard InCHI:	InChI=1S/C32H50O4/c1-9-36-22-18-20-21-19-29(5,26(34)35)15-14-28(21,4)16-17-31(20,7)32(8)13-10-23-27(2,3)24(33)11-12-30(23,6)25(22)32/h18,21-23,25H,9-17,19H2,1-8H3,(H,34,35)/t21-,22+,23-,25+,28+,29-,30-,31+,32+/m0/s1
SMILES:	CCO[C@@H]1C=C2[C@@H]3C[C@](C)(CC[C@]3(C)CC[C@@]2(C)[C@]2(C)CC[C@H]3C(C)(C)C(=O)CC[C@]3(C)[C@@H]12)C(=O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL499319
PubChem CID:	11799513
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
NPO13817	Maytenus undata	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10843569]
NPO13817	Maytenus undata	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ 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
MIC	3

Activity Type	# Activity
Organism	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	>	12.5	ug.mL-1	PMID[470909]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	50.0	ug.mL-1	PMID[470909]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	MIC	=	12.5	ug.mL-1	PMID[470909]

☑ 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 NPC169343 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	208
0.1-0.2	1256
0.2-0.3	4397
0.3-0.4	11967
0.4-0.5	10658
0.5-0.6	6403
0.6-0.7	5424
0.7-0.8	1981
0.8-0.85	224
0.85-0.9	157
0.9-0.95	20
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9767	High Similarity	NPC198818
0.9247	High Similarity	NPC93744
0.9247	High Similarity	NPC476888
0.9222	High Similarity	NPC91010
0.9205	High Similarity	NPC281524
0.9149	High Similarity	NPC476890
0.9149	High Similarity	NPC40918
0.9101	High Similarity	NPC120840
0.9101	High Similarity	NPC113989
0.9053	High Similarity	NPC476889
0.9011	High Similarity	NPC74751
0.9	High Similarity	NPC285184
0.9	High Similarity	NPC60755
0.9	High Similarity	NPC77099
0.9	High Similarity	NPC470590
0.8989	High Similarity	NPC30522
0.8989	High Similarity	NPC474700
0.8953	High Similarity	NPC200752
0.8901	High Similarity	NPC86368
0.8889	High Similarity	NPC474728
0.8851	High Similarity	NPC312660
0.8804	High Similarity	NPC184006
0.8804	High Similarity	NPC296164
0.8804	High Similarity	NPC78580
0.8804	High Similarity	NPC23621
0.8764	High Similarity	NPC162107
0.8764	High Similarity	NPC158141
0.8764	High Similarity	NPC173089
0.8764	High Similarity	NPC46912
0.875	High Similarity	NPC274724
0.8723	High Similarity	NPC26413
0.8721	High Similarity	NPC229584
0.8721	High Similarity	NPC267691
0.8721	High Similarity	NPC162632
0.8721	High Similarity	NPC263272
0.8721	High Similarity	NPC274050
0.8721	High Similarity	NPC14203
0.871	High Similarity	NPC474727
0.871	High Similarity	NPC23241
0.871	High Similarity	NPC195715
0.8696	High Similarity	NPC295643
0.8696	High Similarity	NPC214756
0.8696	High Similarity	NPC272075
0.8681	High Similarity	NPC193750
0.8681	High Similarity	NPC46441
0.8681	High Similarity	NPC291028
0.8667	High Similarity	NPC474474
0.8667	High Similarity	NPC182797
0.8667	High Similarity	NPC474511
0.8667	High Similarity	NPC246708
0.8667	High Similarity	NPC1753
0.8667	High Similarity	NPC40552
0.8667	High Similarity	NPC24816
0.8667	High Similarity	NPC52169
0.8652	High Similarity	NPC329943
0.8652	High Similarity	NPC9892
0.8652	High Similarity	NPC91525
0.8652	High Similarity	NPC322159
0.8652	High Similarity	NPC10005
0.8646	High Similarity	NPC235142
0.8636	High Similarity	NPC96095
0.8632	High Similarity	NPC234617
0.8632	High Similarity	NPC471966
0.8632	High Similarity	NPC124703
0.8621	High Similarity	NPC251779
0.8621	High Similarity	NPC69101
0.8617	High Similarity	NPC327179
0.8617	High Similarity	NPC230151
0.8605	High Similarity	NPC477057
0.8605	High Similarity	NPC267517
0.8605	High Similarity	NPC104545
0.8587	High Similarity	NPC6255
0.8587	High Similarity	NPC105189
0.8587	High Similarity	NPC233455
0.8587	High Similarity	NPC38754
0.8587	High Similarity	NPC471588
0.8587	High Similarity	NPC145067
0.8587	High Similarity	NPC158030
0.8587	High Similarity	NPC65120
0.8587	High Similarity	NPC4036
0.8587	High Similarity	NPC474525
0.8571	High Similarity	NPC293048
0.8571	High Similarity	NPC121798
0.8571	High Similarity	NPC274330
0.8571	High Similarity	NPC263393
0.8571	High Similarity	NPC130520
0.8571	High Similarity	NPC127689
0.8571	High Similarity	NPC64872
0.8571	High Similarity	NPC290972
0.8571	High Similarity	NPC198664
0.8571	High Similarity	NPC234346
0.8571	High Similarity	NPC25906
0.8571	High Similarity	NPC61543
0.8571	High Similarity	NPC470588
0.8571	High Similarity	NPC225585
0.8571	High Similarity	NPC475049
0.8571	High Similarity	NPC270768
0.8571	High Similarity	NPC59263
0.8571	High Similarity	NPC143232
0.8556	High Similarity	NPC242468
0.8556	High Similarity	NPC171203
0.8556	High Similarity	NPC307426
0.8556	High Similarity	NPC88716
0.8556	High Similarity	NPC293564
0.8556	High Similarity	NPC102683
0.8556	High Similarity	NPC68160
0.8556	High Similarity	NPC142415
0.8556	High Similarity	NPC18064
0.8556	High Similarity	NPC98442
0.8556	High Similarity	NPC51700
0.8556	High Similarity	NPC130577
0.8526	High Similarity	NPC476879
0.8526	High Similarity	NPC476878
0.8526	High Similarity	NPC158347
0.8523	High Similarity	NPC70834
0.8506	High Similarity	NPC327002
0.8506	High Similarity	NPC3915
0.8495	Intermediate Similarity	NPC136313
0.8495	Intermediate Similarity	NPC307335
0.8495	Intermediate Similarity	NPC474436
0.8495	Intermediate Similarity	NPC63118
0.8495	Intermediate Similarity	NPC118490
0.8495	Intermediate Similarity	NPC74855
0.8495	Intermediate Similarity	NPC49776
0.8488	Intermediate Similarity	NPC16394
0.8488	Intermediate Similarity	NPC327674
0.8478	Intermediate Similarity	NPC210037
0.8478	Intermediate Similarity	NPC130278
0.8478	Intermediate Similarity	NPC7260
0.8478	Intermediate Similarity	NPC273621
0.8478	Intermediate Similarity	NPC111110
0.8478	Intermediate Similarity	NPC227467
0.8478	Intermediate Similarity	NPC126369
0.8478	Intermediate Similarity	NPC120968
0.8478	Intermediate Similarity	NPC290614
0.8478	Intermediate Similarity	NPC18872
0.8478	Intermediate Similarity	NPC470589
0.8478	Intermediate Similarity	NPC477872
0.8462	Intermediate Similarity	NPC224145
0.8462	Intermediate Similarity	NPC474845
0.8462	Intermediate Similarity	NPC290690
0.8462	Intermediate Similarity	NPC470629
0.8462	Intermediate Similarity	NPC473242
0.8462	Intermediate Similarity	NPC181225
0.8462	Intermediate Similarity	NPC474512
0.8462	Intermediate Similarity	NPC17733
0.8444	Intermediate Similarity	NPC325594
0.8444	Intermediate Similarity	NPC72638
0.8444	Intermediate Similarity	NPC324063
0.8438	Intermediate Similarity	NPC260149
0.8438	Intermediate Similarity	NPC58942
0.8427	Intermediate Similarity	NPC180834
0.8427	Intermediate Similarity	NPC156981
0.8421	Intermediate Similarity	NPC98874
0.8409	Intermediate Similarity	NPC310989
0.8404	Intermediate Similarity	NPC476415
0.8404	Intermediate Similarity	NPC474529
0.8404	Intermediate Similarity	NPC87095
0.84	Intermediate Similarity	NPC301666
0.84	Intermediate Similarity	NPC475570
0.8391	Intermediate Similarity	NPC37038
0.8387	Intermediate Similarity	NPC300351
0.8387	Intermediate Similarity	NPC966
0.8387	Intermediate Similarity	NPC472149
0.8387	Intermediate Similarity	NPC187722
0.8387	Intermediate Similarity	NPC52021
0.8387	Intermediate Similarity	NPC306541
0.8387	Intermediate Similarity	NPC25299
0.8387	Intermediate Similarity	NPC288833
0.8387	Intermediate Similarity	NPC228784
0.8387	Intermediate Similarity	NPC84319
0.8387	Intermediate Similarity	NPC235884
0.8387	Intermediate Similarity	NPC324341
0.8387	Intermediate Similarity	NPC155120
0.8387	Intermediate Similarity	NPC71074
0.8387	Intermediate Similarity	NPC282616
0.8384	Intermediate Similarity	NPC473175
0.8372	Intermediate Similarity	NPC260385
0.8372	Intermediate Similarity	NPC280654
0.8372	Intermediate Similarity	NPC110094
0.837	Intermediate Similarity	NPC161751
0.837	Intermediate Similarity	NPC95246
0.837	Intermediate Similarity	NPC474570
0.837	Intermediate Similarity	NPC474972
0.837	Intermediate Similarity	NPC5509
0.8352	Intermediate Similarity	NPC477228
0.8352	Intermediate Similarity	NPC71507
0.8333	Intermediate Similarity	NPC10057
0.8333	Intermediate Similarity	NPC191965
0.8333	Intermediate Similarity	NPC133954
0.8317	Intermediate Similarity	NPC473483
0.8316	Intermediate Similarity	NPC148523
0.8316	Intermediate Similarity	NPC290481
0.8316	Intermediate Similarity	NPC139570
0.8298	Intermediate Similarity	NPC229281
0.8298	Intermediate Similarity	NPC298554
0.8298	Intermediate Similarity	NPC118519
0.8298	Intermediate Similarity	NPC275809
0.8298	Intermediate Similarity	NPC151722
0.8298	Intermediate Similarity	NPC202728

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 NPC169343 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	179
0.1-0.2	1489
0.2-0.3	3684
0.3-0.4	2474
0.4-0.5	835
0.5-0.6	262
0.6-0.7	186
0.7-0.8	36
0.8-0.85	2
0.85-0.9	2
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9011	High Similarity	NPD7748	Approved
0.8723	High Similarity	NPD7902	Approved
0.8587	High Similarity	NPD7515	Phase 2
0.8404	Intermediate Similarity	NPD7900	Approved
0.8404	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.8105	Intermediate Similarity	NPD6399	Phase 3
0.8065	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7879	Intermediate Similarity	NPD7638	Approved
0.7849	Intermediate Similarity	NPD6684	Approved
0.7849	Intermediate Similarity	NPD7146	Approved
0.7849	Intermediate Similarity	NPD7521	Approved
0.7849	Intermediate Similarity	NPD7334	Approved
0.7849	Intermediate Similarity	NPD6409	Approved
0.7849	Intermediate Similarity	NPD5330	Approved
0.7812	Intermediate Similarity	NPD8034	Phase 2
0.7812	Intermediate Similarity	NPD8035	Phase 2
0.7802	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.78	Intermediate Similarity	NPD7640	Approved
0.78	Intermediate Similarity	NPD7639	Approved
0.7789	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.7684	Intermediate Similarity	NPD6672	Approved
0.7684	Intermediate Similarity	NPD6903	Approved
0.7684	Intermediate Similarity	NPD5737	Approved
0.7634	Intermediate Similarity	NPD4786	Approved
0.7609	Intermediate Similarity	NPD3667	Approved
0.76	Intermediate Similarity	NPD6083	Phase 2
0.76	Intermediate Similarity	NPD6084	Phase 2
0.7553	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7473	Intermediate Similarity	NPD7645	Phase 2
0.7449	Intermediate Similarity	NPD5693	Phase 1
0.7447	Intermediate Similarity	NPD3665	Phase 1
0.7447	Intermediate Similarity	NPD3666	Approved
0.7447	Intermediate Similarity	NPD3133	Approved
0.7423	Intermediate Similarity	NPD6051	Approved
0.7416	Intermediate Similarity	NPD8039	Approved
0.74	Intermediate Similarity	NPD5695	Phase 3
0.7387	Intermediate Similarity	NPD7115	Discovery
0.7368	Intermediate Similarity	NPD1694	Approved
0.7353	Intermediate Similarity	NPD5696	Approved
0.7327	Intermediate Similarity	NPD7614	Phase 1
0.7327	Intermediate Similarity	NPD7732	Phase 3
0.7292	Intermediate Similarity	NPD3618	Phase 1
0.7292	Intermediate Similarity	NPD6098	Approved
0.729	Intermediate Similarity	NPD6686	Approved
0.7273	Intermediate Similarity	NPD6411	Approved
0.7264	Intermediate Similarity	NPD7128	Approved
0.7264	Intermediate Similarity	NPD6675	Approved
0.7264	Intermediate Similarity	NPD6402	Approved
0.7264	Intermediate Similarity	NPD5739	Approved
0.7263	Intermediate Similarity	NPD3668	Phase 3
0.7245	Intermediate Similarity	NPD6673	Approved
0.7245	Intermediate Similarity	NPD5328	Approved
0.7245	Intermediate Similarity	NPD6080	Approved
0.7245	Intermediate Similarity	NPD6904	Approved
0.7216	Intermediate Similarity	NPD3573	Approved
0.7204	Intermediate Similarity	NPD4695	Discontinued
0.7143	Intermediate Similarity	NPD7632	Discontinued
0.713	Intermediate Similarity	NPD7320	Approved
0.713	Intermediate Similarity	NPD6881	Approved
0.713	Intermediate Similarity	NPD6899	Approved
0.7113	Intermediate Similarity	NPD4623	Approved
0.7113	Intermediate Similarity	NPD4519	Discontinued
0.71	Intermediate Similarity	NPD6079	Approved
0.7091	Intermediate Similarity	NPD8130	Phase 1
0.7071	Intermediate Similarity	NPD4753	Phase 2
0.7071	Intermediate Similarity	NPD6101	Approved
0.7071	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7064	Intermediate Similarity	NPD6373	Approved
0.7064	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7064	Intermediate Similarity	NPD6372	Approved
0.7059	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7053	Intermediate Similarity	NPD4221	Approved
0.7053	Intermediate Similarity	NPD4223	Phase 3
0.7037	Intermediate Similarity	NPD5697	Approved
0.7037	Intermediate Similarity	NPD6412	Phase 2
0.7037	Intermediate Similarity	NPD5701	Approved
0.703	Intermediate Similarity	NPD5778	Approved
0.703	Intermediate Similarity	NPD5779	Approved
0.7027	Intermediate Similarity	NPD8297	Approved
0.7019	Intermediate Similarity	NPD4225	Approved
0.701	Intermediate Similarity	NPD5329	Approved
0.7009	Intermediate Similarity	NPD8328	Phase 3
0.7	Intermediate Similarity	NPD7102	Approved
0.7	Intermediate Similarity	NPD7290	Approved
0.7	Intermediate Similarity	NPD6883	Approved
0.6989	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6972	Remote Similarity	NPD6011	Approved
0.697	Remote Similarity	NPD5208	Approved
0.6964	Remote Similarity	NPD8133	Approved
0.6939	Remote Similarity	NPD5279	Phase 3
0.6937	Remote Similarity	NPD6617	Approved
0.6937	Remote Similarity	NPD6869	Approved
0.6937	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6937	Remote Similarity	NPD6649	Approved
0.6937	Remote Similarity	NPD6847	Approved
0.6937	Remote Similarity	NPD6650	Approved
0.6931	Remote Similarity	NPD6050	Approved
0.6931	Remote Similarity	NPD5281	Approved
0.6931	Remote Similarity	NPD5284	Approved
0.6909	Remote Similarity	NPD6012	Approved
0.6909	Remote Similarity	NPD6013	Approved
0.6909	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6909	Remote Similarity	NPD6014	Approved
0.6907	Remote Similarity	NPD4197	Approved
0.6875	Remote Similarity	NPD6882	Approved
0.6863	Remote Similarity	NPD4202	Approved
0.6847	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6832	Remote Similarity	NPD5785	Approved
0.6832	Remote Similarity	NPD5692	Phase 3
0.6827	Remote Similarity	NPD4697	Phase 3
0.6827	Remote Similarity	NPD5221	Approved
0.6827	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6827	Remote Similarity	NPD5222	Approved
0.6809	Remote Similarity	NPD3617	Approved
0.6804	Remote Similarity	NPD4788	Approved
0.6783	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6768	Remote Similarity	NPD4690	Approved
0.6768	Remote Similarity	NPD4689	Approved
0.6768	Remote Similarity	NPD5205	Approved
0.6768	Remote Similarity	NPD4138	Approved
0.6768	Remote Similarity	NPD4693	Phase 3
0.6768	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6768	Remote Similarity	NPD4688	Approved
0.6765	Remote Similarity	NPD7637	Suspended
0.6765	Remote Similarity	NPD5694	Approved
0.6762	Remote Similarity	NPD5173	Approved
0.6762	Remote Similarity	NPD4755	Approved
0.675	Remote Similarity	NPD7507	Approved
0.6731	Remote Similarity	NPD5210	Approved
0.6731	Remote Similarity	NPD4629	Approved
0.6726	Remote Similarity	NPD6053	Discontinued
0.6703	Remote Similarity	NPD5777	Approved
0.6696	Remote Similarity	NPD6868	Approved
0.6667	Remote Similarity	NPD6698	Approved
0.6667	Remote Similarity	NPD46	Approved
0.6667	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5211	Phase 2
0.6667	Remote Similarity	NPD6942	Approved
0.6667	Remote Similarity	NPD5207	Approved
0.6667	Remote Similarity	NPD7339	Approved
0.6667	Remote Similarity	NPD7525	Registered
0.6636	Remote Similarity	NPD4696	Approved
0.6636	Remote Similarity	NPD6008	Approved
0.6636	Remote Similarity	NPD5285	Approved
0.6636	Remote Similarity	NPD5286	Approved
0.6636	Remote Similarity	NPD4700	Approved
0.6635	Remote Similarity	NPD6001	Approved
0.6633	Remote Similarity	NPD5362	Discontinued
0.6633	Remote Similarity	NPD7154	Phase 3
0.661	Remote Similarity	NPD8294	Approved
0.661	Remote Similarity	NPD8377	Approved
0.66	Remote Similarity	NPD5280	Approved
0.66	Remote Similarity	NPD4694	Approved
0.66	Remote Similarity	NPD5690	Phase 2
0.6596	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6596	Remote Similarity	NPD6117	Approved
0.6585	Remote Similarity	NPD7319	Approved
0.6581	Remote Similarity	NPD6335	Approved
0.6577	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6574	Remote Similarity	NPD5223	Approved
0.6571	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6566	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6559	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6555	Remote Similarity	NPD8380	Approved
0.6555	Remote Similarity	NPD8335	Approved
0.6555	Remote Similarity	NPD8033	Approved
0.6555	Remote Similarity	NPD8379	Approved
0.6555	Remote Similarity	NPD8378	Approved
0.6555	Remote Similarity	NPD8296	Approved
0.6552	Remote Similarity	NPD6274	Approved
0.6545	Remote Similarity	NPD5141	Approved
0.6531	Remote Similarity	NPD4269	Approved
0.6531	Remote Similarity	NPD4270	Approved
0.6531	Remote Similarity	NPD6435	Approved
0.6526	Remote Similarity	NPD6116	Phase 1
0.6525	Remote Similarity	NPD7101	Approved
0.6525	Remote Similarity	NPD7100	Approved
0.6522	Remote Similarity	NPD7094	Approved
0.6522	Remote Similarity	NPD6081	Approved
0.6522	Remote Similarity	NPD4632	Approved
0.6522	Remote Similarity	NPD6858	Approved
0.6517	Remote Similarity	NPD4224	Phase 2
0.6514	Remote Similarity	NPD5224	Approved
0.6514	Remote Similarity	NPD5225	Approved
0.6514	Remote Similarity	NPD5226	Approved
0.6514	Remote Similarity	NPD4633	Approved
0.6504	Remote Similarity	NPD7736	Approved
0.65	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6496	Remote Similarity	NPD6317	Approved
0.6491	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6484	Remote Similarity	NPD4137	Phase 3
0.6481	Remote Similarity	NPD6404	Discontinued
0.6458	Remote Similarity	NPD6114	Approved
0.6458	Remote Similarity	NPD6118	Approved
0.6458	Remote Similarity	NPD6697	Approved
0.6458	Remote Similarity	NPD6115	Approved
0.6455	Remote Similarity	NPD6052	Approved
0.6455	Remote Similarity	NPD5174	Approved
0.6455	Remote Similarity	NPD5175	Approved
0.6455	Remote Similarity	NPD4754	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