NPASS Compound

Structure

NPC469447 OpenBabel07101719512D 45 50 0 0 1 0 0 0 0 0999 V2000 -3.6499 -0.9470 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1740 0.5968 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3766 -1.9608 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8864 -1.1117 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6981 1.9608 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8490 -2.4510 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8490 0.4902 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.4904 -2.9412 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7924 -2.9412 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8490 -1.4706 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.3395 -3.4314 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.9608 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9433 -3.4314 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5471 -0.4902 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5471 -3.4314 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6981 -2.9412 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6981 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3962 0.9804 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5471 1.4706 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8490 1.4706 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 0.9804 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.6414 -4.4118 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5471 -0.4902 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.6414 -3.4314 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8490 -0.4902 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6981 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 9.3395 -4.4118 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.4904 -4.9020 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5471 -1.4706 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8490 -1.4706 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.3962 -2.9412 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.0943 -2.9412 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6981 0.9804 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3962 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3962 -1.9608 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6981 0.9804 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6981 -1.9608 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8490 -0.4902 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 10.1885 -4.9020 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 8.4904 -5.8824 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.0943 -1.9608 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5471 0.4902 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6981 1.9608 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2452 -3.4314 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 34 1 0 0 0 0 2 34 1 0 0 0 0 3 35 1 0 0 0 0 4 35 1 0 0 0 0 7 38 1 0 0 0 0 8 11 2 0 0 0 0 8 24 1 0 0 0 0 9 13 2 0 0 0 0 9 24 1 0 0 0 0 10 12 1 0 0 0 0 10 25 2 0 0 0 0 11 27 1 0 0 0 0 12 30 1 0 0 0 0 13 32 1 0 0 0 0 14 17 1 0 0 0 0 14 29 1 0 0 0 0 15 16 1 0 0 0 0 15 31 1 0 0 0 0 16 37 1 0 0 0 0 17 38 1 0 0 0 0 18 19 1 0 0 0 0 18 34 1 0 0 0 0 19 36 1 0 0 0 0 20 21 1 0 0 0 0 20 36 1 0 0 0 0 21 39 1 0 0 0 0 22 24 2 0 0 0 0 22 28 1 0 0 0 0 23 26 1 0 0 0 0 23 34 1 0 0 0 0 25 26 1 0 0 0 0 25 39 1 0 0 0 0 26 36 1 6 0 0 0 27 28 2 0 0 0 0 27 40 1 0 0 0 0 28 41 1 0 0 0 0 29 35 1 0 0 0 0 29 37 1 1 0 0 0 30 37 1 1 0 0 0 30 38 1 0 0 0 0 31 35 1 0 0 0 0 31 45 1 6 0 0 0 32 42 2 0 0 0 0 32 45 1 0 0 0 0 33 43 2 0 0 0 0 33 44 1 0 0 0 0 36 5 1 1 0 0 0 37 6 1 1 0 0 0 38 39 1 6 0 0 0 39 33 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	618.39
Volume:	666.047
LogP:	7.148
LogD:	5.425
LogS:	-4.638
# Rotatable Bonds:	5
TPSA:	104.06
# H-Bond Aceptor:	6
# H-Bond Donor:	3
# Rings:	6
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.135
Synthetic Accessibility Score:	4.933
Fsp3:	0.692
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.353
MDCK Permeability:	1.5765825082780793e-05
Pgp-inhibitor:	0.048
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.008
20% Bioavailability (F20%):	0.521
30% Bioavailability (F30%):	0.66

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.024
Plasma Protein Binding (PPB):	101.27690124511719%
Volume Distribution (VD):	0.566
Pgp-substrate:	2.320446252822876%

ADMET: Metabolism

CYP1A2-inhibitor:	0.029
CYP1A2-substrate:	0.318
CYP2C19-inhibitor:	0.204
CYP2C19-substrate:	0.567
CYP2C9-inhibitor:	0.111
CYP2C9-substrate:	0.986
CYP2D6-inhibitor:	0.214
CYP2D6-substrate:	0.472
CYP3A4-inhibitor:	0.123
CYP3A4-substrate:	0.228

ADMET: Excretion

Clearance (CL):	1.354
Half-life (T1/2):	0.177

ADMET: Toxicity

hERG Blockers:	0.06
Human Hepatotoxicity (H-HT):	0.415
Drug-inuced Liver Injury (DILI):	0.014
AMES Toxicity:	0.007
Rat Oral Acute Toxicity:	0.04
Maximum Recommended Daily Dose:	0.946
Skin Sensitization:	0.764
Carcinogencity:	0.01
Eye Corrosion:	0.005
Eye Irritation:	0.854
Respiratory Toxicity:	0.603

Download Data

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

Natural Product: NPC469447

Natural Product ID:	NPC469447
*Common Name:**	3Alpha-O-Caffeoylolean-12-En-27-Oic Acid
IUPAC Name:	(4aR,6aR,6aR,6bR,8aR,10R,12aR,14bR)-10-[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy-2,2,4a,6b,9,9,12a-heptamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-6a-carboxylic acid
Synonyms:
Standard InCHIKey:	LWJORTCWCRJUEH-QHCDZFOOSA-N
Standard InCHI:	InChI=1S/C39H54O6/c1-34(2)18-19-36(5)20-21-39(33(43)44)25(26(36)23-34)10-12-30-37(6)16-15-31(35(3,4)29(37)14-17-38(30,39)7)45-32(42)13-9-24-8-11-27(40)28(41)22-24/h8-11,13,22,26,29-31,40-41H,12,14-21,23H2,1-7H3,(H,43,44)/b13-9+/t26-,29-,30+,31+,36+,37-,38+,39+/m0/s1
SMILES:	O=C(O[C@@H]1CC[C@]2([C@H](C1(C)C)CC[C@@]1([C@@H]2CC=C2[C@]1(CC[C@@]1([C@H]2CC(C)(C)CC1)C)C(=O)O)C)C)/C=C/c1ccc(c(c1)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1079030
PubChem CID:	44254694
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
NPO24475	Aceriphyllum rossii	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[19618898]
NPO24475	Aceriphyllum rossii	n.a.	n.a.	n.a.	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
IC50	2

Activity Type	# Activity
Cell Line	1
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT83	Cell Line	MCF7	Homo sapiens	IC50	>	150000.0	nM	PMID[514039]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	150000.0	nM	PMID[514039]

☑ 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 NPC469447 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	332
0.1-0.2	1294
0.2-0.3	2572
0.3-0.4	5327
0.4-0.5	9513
0.5-0.6	10450
0.6-0.7	11228
0.7-0.8	1778
0.8-0.85	72
0.85-0.9	51
0.9-0.95	61
0.95-1	19

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC477873
0.9854	High Similarity	NPC53520
0.964	High Similarity	NPC8102
0.964	High Similarity	NPC66894
0.9562	High Similarity	NPC27518
0.9562	High Similarity	NPC304110
0.9559	High Similarity	NPC182249
0.9489	High Similarity	NPC271494
0.9489	High Similarity	NPC473591
0.9489	High Similarity	NPC155192
0.9485	High Similarity	NPC471152
0.9481	High Similarity	NPC477874
0.9481	High Similarity	NPC173569
0.9441	High Similarity	NPC118033
0.9412	High Similarity	NPC249817
0.9375	High Similarity	NPC473773
0.9375	High Similarity	NPC475579
0.9357	High Similarity	NPC25491
0.9343	High Similarity	NPC22676
0.9343	High Similarity	NPC475482
0.9343	High Similarity	NPC198621
0.9343	High Similarity	NPC216940
0.9338	High Similarity	NPC43353
0.9306	High Similarity	NPC473680
0.9306	High Similarity	NPC473579
0.9306	High Similarity	NPC475454
0.9306	High Similarity	NPC475311
0.9281	High Similarity	NPC473612
0.9214	High Similarity	NPC35212
0.9178	High Similarity	NPC205392
0.9178	High Similarity	NPC105942
0.9155	High Similarity	NPC307205
0.9149	High Similarity	NPC235557
0.9149	High Similarity	NPC310621
0.9149	High Similarity	NPC252133
0.9143	High Similarity	NPC172311
0.9137	High Similarity	NPC234548
0.9137	High Similarity	NPC248287
0.9085	High Similarity	NPC26045
0.9051	High Similarity	NPC475627
0.9051	High Similarity	NPC475346
0.9051	High Similarity	NPC475457
0.9051	High Similarity	NPC18982
0.9037	High Similarity	NPC86257
0.9007	High Similarity	NPC472801
0.8913	High Similarity	NPC476282
0.8865	High Similarity	NPC139243
0.8865	High Similarity	NPC116742
0.8844	High Similarity	NPC327962
0.8803	High Similarity	NPC470617
0.8803	High Similarity	NPC471875
0.8803	High Similarity	NPC470616
0.8768	High Similarity	NPC243305
0.8758	High Similarity	NPC266365
0.8741	High Similarity	NPC470035
0.8741	High Similarity	NPC137416
0.8716	High Similarity	NPC145527
0.8716	High Similarity	NPC470618
0.8716	High Similarity	NPC470619
0.8716	High Similarity	NPC208785
0.8714	High Similarity	NPC11266
0.8707	High Similarity	NPC325032
0.8707	High Similarity	NPC477483
0.8652	High Similarity	NPC472804
0.863	High Similarity	NPC235195
0.863	High Similarity	NPC280717
0.863	High Similarity	NPC271607
0.863	High Similarity	NPC19862
0.8621	High Similarity	NPC184935
0.8601	High Similarity	NPC132723
0.8601	High Similarity	NPC76032
0.8582	High Similarity	NPC194970
0.8581	High Similarity	NPC32017
0.8581	High Similarity	NPC96930
0.8553	High Similarity	NPC472807
0.8543	High Similarity	NPC475216
0.8543	High Similarity	NPC475595
0.8543	High Similarity	NPC475145
0.8543	High Similarity	NPC266084
0.8543	High Similarity	NPC83663
0.8543	High Similarity	NPC475162
0.8543	High Similarity	NPC473544
0.854	High Similarity	NPC190849
0.854	High Similarity	NPC171007
0.8535	High Similarity	NPC200726
0.8529	High Similarity	NPC10154
0.8529	High Similarity	NPC265413
0.8523	High Similarity	NPC273358
0.8523	High Similarity	NPC46549
0.8523	High Similarity	NPC264229
0.8523	High Similarity	NPC279442
0.8523	High Similarity	NPC298647
0.8523	High Similarity	NPC292206
0.8521	High Similarity	NPC103082
0.8489	Intermediate Similarity	NPC30174
0.8481	Intermediate Similarity	NPC177362
0.8462	Intermediate Similarity	NPC476699
0.8446	Intermediate Similarity	NPC470038
0.8446	Intermediate Similarity	NPC75295
0.8446	Intermediate Similarity	NPC258856
0.8438	Intermediate Similarity	NPC469774
0.8438	Intermediate Similarity	NPC32723
0.8438	Intermediate Similarity	NPC469777
0.8438	Intermediate Similarity	NPC469775
0.8438	Intermediate Similarity	NPC469778
0.8438	Intermediate Similarity	NPC135334
0.8438	Intermediate Similarity	NPC469776
0.8438	Intermediate Similarity	NPC469772
0.8438	Intermediate Similarity	NPC469773
0.8438	Intermediate Similarity	NPC100925
0.8438	Intermediate Similarity	NPC295941
0.8428	Intermediate Similarity	NPC266545
0.8428	Intermediate Similarity	NPC202428
0.8389	Intermediate Similarity	NPC472937
0.8389	Intermediate Similarity	NPC472938
0.8389	Intermediate Similarity	NPC472936
0.8387	Intermediate Similarity	NPC471750
0.8375	Intermediate Similarity	NPC472803
0.8345	Intermediate Similarity	NPC471974
0.8345	Intermediate Similarity	NPC469680
0.8345	Intermediate Similarity	NPC469681
0.8322	Intermediate Similarity	NPC471913
0.8313	Intermediate Similarity	NPC471870
0.8311	Intermediate Similarity	NPC477207
0.8299	Intermediate Similarity	NPC472410
0.8289	Intermediate Similarity	NPC470037
0.8278	Intermediate Similarity	NPC473719
0.8278	Intermediate Similarity	NPC477206
0.8276	Intermediate Similarity	NPC277559
0.8276	Intermediate Similarity	NPC49911
0.8267	Intermediate Similarity	NPC474991
0.8267	Intermediate Similarity	NPC273798
0.8264	Intermediate Similarity	NPC279463
0.8261	Intermediate Similarity	NPC474532
0.8248	Intermediate Similarity	NPC478058
0.8243	Intermediate Similarity	NPC30846
0.8243	Intermediate Similarity	NPC471971
0.8243	Intermediate Similarity	NPC469855
0.8243	Intermediate Similarity	NPC471972
0.8235	Intermediate Similarity	NPC470848
0.8235	Intermediate Similarity	NPC470849
0.8231	Intermediate Similarity	NPC38473
0.8231	Intermediate Similarity	NPC29599
0.8227	Intermediate Similarity	NPC475138
0.8227	Intermediate Similarity	NPC131684
0.8224	Intermediate Similarity	NPC472939
0.8207	Intermediate Similarity	NPC7464
0.82	Intermediate Similarity	NPC84786
0.82	Intermediate Similarity	NPC320734
0.8188	Intermediate Similarity	NPC471876
0.8188	Intermediate Similarity	NPC199936
0.8182	Intermediate Similarity	NPC471874
0.8163	Intermediate Similarity	NPC106055
0.8163	Intermediate Similarity	NPC110699
0.816	Intermediate Similarity	NPC471871
0.8158	Intermediate Similarity	NPC132810
0.8148	Intermediate Similarity	NPC203124
0.8148	Intermediate Similarity	NPC309434
0.8146	Intermediate Similarity	NPC246229
0.8146	Intermediate Similarity	NPC471970
0.8146	Intermediate Similarity	NPC191899
0.8143	Intermediate Similarity	NPC470753
0.8143	Intermediate Similarity	NPC473220
0.8141	Intermediate Similarity	NPC471968
0.8133	Intermediate Similarity	NPC145301
0.8133	Intermediate Similarity	NPC144247
0.8133	Intermediate Similarity	NPC469856
0.8133	Intermediate Similarity	NPC469375
0.8133	Intermediate Similarity	NPC469854
0.8133	Intermediate Similarity	NPC294679
0.8133	Intermediate Similarity	NPC8493
0.8129	Intermediate Similarity	NPC288945
0.8129	Intermediate Similarity	NPC62051
0.8125	Intermediate Similarity	NPC475468
0.8125	Intermediate Similarity	NPC168799
0.8125	Intermediate Similarity	NPC155209
0.8117	Intermediate Similarity	NPC124842
0.8113	Intermediate Similarity	NPC471873
0.8112	Intermediate Similarity	NPC198388
0.8108	Intermediate Similarity	NPC82336
0.8108	Intermediate Similarity	NPC78987
0.8105	Intermediate Similarity	NPC142654
0.8099	Intermediate Similarity	NPC470747
0.8095	Intermediate Similarity	NPC42384
0.8095	Intermediate Similarity	NPC5014
0.8095	Intermediate Similarity	NPC289358
0.8095	Intermediate Similarity	NPC50615
0.8095	Intermediate Similarity	NPC469857
0.8095	Intermediate Similarity	NPC477849
0.8095	Intermediate Similarity	NPC51531
0.8095	Intermediate Similarity	NPC91887
0.8095	Intermediate Similarity	NPC28592
0.8095	Intermediate Similarity	NPC245760
0.8095	Intermediate Similarity	NPC23667
0.8095	Intermediate Similarity	NPC473479
0.8095	Intermediate Similarity	NPC165191
0.8095	Intermediate Similarity	NPC149773
0.8095	Intermediate Similarity	NPC46242
0.8095	Intermediate Similarity	NPC297797
0.8095	Intermediate Similarity	NPC114333

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 NPC469447 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	280
0.1-0.2	846
0.2-0.3	1483
0.3-0.4	2659
0.4-0.5	2147
0.5-0.6	1253
0.6-0.7	455
0.7-0.8	26
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9779	High Similarity	NPD8166	Discontinued
0.8112	Intermediate Similarity	NPD6663	Approved
0.8085	Intermediate Similarity	NPD5736	Approved
0.805	Intermediate Similarity	NPD8127	Discontinued
0.7933	Intermediate Similarity	NPD7003	Approved
0.7871	Intermediate Similarity	NPD7458	Discontinued
0.7792	Intermediate Similarity	NPD6273	Approved
0.7719	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD6190	Approved
0.7643	Intermediate Similarity	NPD3019	Approved
0.7643	Intermediate Similarity	NPD2932	Approved
0.7616	Intermediate Similarity	NPD7266	Discontinued
0.7582	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7582	Intermediate Similarity	NPD4110	Phase 3
0.7544	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD8032	Phase 2
0.75	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD6234	Discontinued
0.7485	Intermediate Similarity	NPD7228	Approved
0.7468	Intermediate Similarity	NPD4628	Phase 3
0.7468	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.745	Intermediate Similarity	NPD3620	Phase 2
0.745	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.74	Intermediate Similarity	NPD6355	Discontinued
0.7375	Intermediate Similarity	NPD7028	Phase 2
0.7365	Intermediate Similarity	NPD7095	Approved
0.7362	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7353	Intermediate Similarity	NPD3021	Approved
0.7353	Intermediate Similarity	NPD3022	Approved
0.7333	Intermediate Similarity	NPD4060	Phase 1
0.7333	Intermediate Similarity	NPD4140	Approved
0.732	Intermediate Similarity	NPD5408	Approved
0.732	Intermediate Similarity	NPD5404	Approved
0.732	Intermediate Similarity	NPD5405	Approved
0.732	Intermediate Similarity	NPD5406	Approved
0.7315	Intermediate Similarity	NPD3764	Approved
0.7315	Intermediate Similarity	NPD6798	Discontinued
0.7312	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD3455	Phase 2
0.731	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD7097	Phase 1
0.7292	Intermediate Similarity	NPD3092	Approved
0.7285	Intermediate Similarity	NPD230	Phase 1
0.7284	Intermediate Similarity	NPD37	Approved
0.7278	Intermediate Similarity	NPD4160	Clinical (unspecified phase)
0.7261	Intermediate Similarity	NPD7236	Approved
0.726	Intermediate Similarity	NPD1283	Approved
0.7256	Intermediate Similarity	NPD4966	Approved
0.7256	Intermediate Similarity	NPD4967	Phase 2
0.7256	Intermediate Similarity	NPD4965	Approved
0.7254	Intermediate Similarity	NPD3091	Approved
0.7248	Intermediate Similarity	NPD7008	Discontinued
0.7248	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7235	Intermediate Similarity	NPD5844	Phase 1
0.7225	Intermediate Similarity	NPD8313	Approved
0.7225	Intermediate Similarity	NPD8312	Approved
0.7222	Intermediate Similarity	NPD3026	Approved
0.7222	Intermediate Similarity	NPD3023	Approved
0.7219	Intermediate Similarity	NPD826	Approved
0.7219	Intermediate Similarity	NPD825	Approved
0.7215	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7214	Intermediate Similarity	NPD2629	Approved
0.7211	Intermediate Similarity	NPD3094	Phase 2
0.7208	Intermediate Similarity	NPD2935	Discontinued
0.7203	Intermediate Similarity	NPD3025	Approved
0.7203	Intermediate Similarity	NPD3024	Approved
0.72	Intermediate Similarity	NPD8150	Discontinued
0.717	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7153	Intermediate Similarity	NPD4626	Approved
0.7152	Intermediate Similarity	NPD7768	Phase 2
0.7151	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7118	Intermediate Similarity	NPD7473	Discontinued
0.7105	Intermediate Similarity	NPD2979	Phase 3
0.7097	Intermediate Similarity	NPD2438	Suspended
0.7095	Intermediate Similarity	NPD2797	Approved
0.7089	Intermediate Similarity	NPD7910	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD5691	Approved
0.707	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD5735	Approved
0.7055	Intermediate Similarity	NPD1281	Approved
0.7042	Intermediate Similarity	NPD4198	Discontinued
0.7041	Intermediate Similarity	NPD6232	Discontinued
0.7039	Intermediate Similarity	NPD6233	Phase 2
0.7037	Intermediate Similarity	NPD7239	Suspended
0.7034	Intermediate Similarity	NPD3095	Discontinued
0.7032	Intermediate Similarity	NPD3299	Clinical (unspecified phase)
0.7032	Intermediate Similarity	NPD2799	Discontinued
0.703	Intermediate Similarity	NPD8455	Phase 2
0.703	Intermediate Similarity	NPD7819	Suspended
0.7029	Intermediate Similarity	NPD3534	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD3750	Approved
0.7014	Intermediate Similarity	NPD9545	Approved
0.7012	Intermediate Similarity	NPD6677	Suspended
0.7011	Intermediate Similarity	NPD7685	Pre-registration
0.7011	Intermediate Similarity	NPD7240	Approved
0.7	Intermediate Similarity	NPD9494	Approved
0.6988	Remote Similarity	NPD8438	Clinical (unspecified phase)
0.698	Remote Similarity	NPD1470	Approved
0.6974	Remote Similarity	NPD3268	Approved
0.6972	Remote Similarity	NPD5951	Approved
0.697	Remote Similarity	NPD1934	Approved
0.6959	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD6166	Phase 2
0.6959	Remote Similarity	NPD5327	Phase 3
0.6957	Remote Similarity	NPD7446	Clinical (unspecified phase)
0.695	Remote Similarity	NPD6858	Approved
0.695	Remote Similarity	NPD7094	Approved
0.6948	Remote Similarity	NPD555	Phase 2
0.6944	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6943	Remote Similarity	NPD5762	Approved
0.6943	Remote Similarity	NPD5763	Approved
0.6943	Remote Similarity	NPD2346	Discontinued
0.6939	Remote Similarity	NPD1201	Approved
0.6933	Remote Similarity	NPD257	Approved
0.6933	Remote Similarity	NPD258	Approved
0.6918	Remote Similarity	NPD7163	Clinical (unspecified phase)
0.691	Remote Similarity	NPD8434	Phase 2
0.6909	Remote Similarity	NPD6873	Phase 2
0.6906	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD7075	Discontinued
0.6901	Remote Similarity	NPD4869	Clinical (unspecified phase)
0.6899	Remote Similarity	NPD4534	Discontinued
0.6897	Remote Similarity	NPD7074	Phase 3
0.6894	Remote Similarity	NPD7390	Discontinued
0.6886	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6883	Remote Similarity	NPD943	Approved
0.6882	Remote Similarity	NPD7199	Phase 2
0.6879	Remote Similarity	NPD6100	Approved
0.6879	Remote Similarity	NPD6099	Approved
0.6879	Remote Similarity	NPD2531	Phase 2
0.686	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6855	Remote Similarity	NPD6674	Discontinued
0.6849	Remote Similarity	NPD1651	Approved
0.6849	Remote Similarity	NPD5585	Approved
0.6839	Remote Similarity	NPD7054	Approved
0.6832	Remote Similarity	NPD3300	Phase 2
0.6828	Remote Similarity	NPD5536	Phase 2
0.6826	Remote Similarity	NPD1465	Phase 2
0.6826	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD4062	Phase 3
0.6818	Remote Similarity	NPD259	Phase 1
0.6818	Remote Similarity	NPD7961	Discontinued
0.6803	Remote Similarity	NPD1778	Approved
0.6803	Remote Similarity	NPD4059	Approved
0.6802	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.68	Remote Similarity	NPD7472	Approved
0.6798	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6797	Remote Similarity	NPD3027	Phase 3
0.6795	Remote Similarity	NPD6353	Approved
0.6795	Remote Similarity	NPD6653	Approved
0.6792	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6788	Remote Similarity	NPD3226	Approved
0.6784	Remote Similarity	NPD6959	Discontinued
0.6783	Remote Similarity	NPD5283	Phase 1
0.6779	Remote Similarity	NPD3972	Approved
0.6779	Remote Similarity	NPD9269	Phase 2
0.6779	Remote Similarity	NPD1608	Approved
0.6772	Remote Similarity	NPD4477	Approved
0.6772	Remote Similarity	NPD4476	Approved
0.6761	Remote Similarity	NPD228	Approved
0.6759	Remote Similarity	NPD9493	Approved
0.6757	Remote Similarity	NPD3496	Discontinued
0.6755	Remote Similarity	NPD7680	Approved
0.6755	Remote Similarity	NPD1164	Approved
0.6753	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6747	Remote Similarity	NPD4380	Phase 2
0.6747	Remote Similarity	NPD6599	Discontinued
0.6746	Remote Similarity	NPD3882	Suspended
0.6739	Remote Similarity	NPD5909	Discontinued
0.6735	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.6733	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.6731	Remote Similarity	NPD3657	Discovery
0.6731	Remote Similarity	NPD447	Suspended
0.673	Remote Similarity	NPD7702	Clinical (unspecified phase)
0.673	Remote Similarity	NPD2029	Clinical (unspecified phase)
0.6726	Remote Similarity	NPD2801	Approved
0.6723	Remote Similarity	NPD7251	Discontinued
0.672	Remote Similarity	NPD7237	Clinical (unspecified phase)
0.6711	Remote Similarity	NPD4624	Approved
0.6711	Remote Similarity	NPD2798	Approved
0.6709	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.6709	Remote Similarity	NPD4308	Phase 3
0.6709	Remote Similarity	NPD3748	Approved
0.6707	Remote Similarity	NPD7411	Suspended
0.6706	Remote Similarity	NPD7832	Clinical (unspecified phase)
0.6706	Remote Similarity	NPD7833	Phase 2
0.6706	Remote Similarity	NPD7831	Phase 2
0.6705	Remote Similarity	NPD8051	Clinical (unspecified phase)
0.6703	Remote Similarity	NPD2490	Approved
0.6703	Remote Similarity	NPD2488	Approved
0.6691	Remote Similarity	NPD3020	Approved
0.669	Remote Similarity	NPD7157	Approved
0.6689	Remote Similarity	NPD8651	Approved
0.6689	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6687	Remote Similarity	NPD5958	Discontinued
0.6687	Remote Similarity	NPD1511	Approved
0.6686	Remote Similarity	NPD3817	Phase 2
0.6686	Remote Similarity	NPD3818	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