NPASS Compound

Structure

NPC43353 OpenBabel07101718282D 44 49 0 0 1 0 0 0 0 0999 V2000 1.8532 4.1230 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4515 3.8050 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0361 -2.3187 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0561 -2.3187 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6974 0.9800 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8487 -1.4700 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8487 -0.4900 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9409 -1.4700 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.6383 -1.4700 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.9600 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0922 -0.9800 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.4870 -0.9800 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8487 1.4700 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3948 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8487 -1.4700 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5461 0.4900 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.9800 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3948 2.9400 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6974 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3948 1.9600 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5461 0.4900 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7896 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6974 2.9400 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7896 -0.9800 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8487 1.4700 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3948 -0.9800 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6974 1.9600 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.2435 -1.4700 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.4870 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.6383 0.4900 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6974 -0.9800 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8487 0.4900 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.3948 0.9800 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5461 3.4300 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5461 -1.4700 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6974 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8487 0.4900 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 2.5461 1.4700 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.2435 -2.4500 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.3358 0.4900 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.6383 1.4700 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3948 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2435 1.4700 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 6 37 1 0 0 0 0 8 11 2 0 0 0 0 8 24 1 0 0 0 0 9 12 2 0 0 0 0 9 24 1 0 0 0 0 10 13 1 0 0 0 0 10 25 2 0 0 0 0 11 28 1 0 0 0 0 12 29 1 0 0 0 0 13 32 1 0 0 0 0 14 16 1 0 0 0 0 14 26 1 0 0 0 0 15 17 1 0 0 0 0 15 31 1 0 0 0 0 16 36 1 0 0 0 0 17 38 1 0 0 0 0 18 20 1 0 0 0 0 18 34 1 0 0 0 0 19 21 1 0 0 0 0 19 37 1 0 0 0 0 20 39 1 0 0 0 0 21 39 1 0 0 0 0 22 24 2 0 0 0 0 22 30 1 0 0 0 0 23 27 1 0 0 0 0 23 34 1 0 0 0 0 25 27 1 0 0 0 0 25 37 1 0 0 0 0 26 28 1 1 0 0 0 26 35 1 0 0 0 0 27 39 1 6 0 0 0 28 40 2 0 0 0 0 29 30 2 0 0 0 0 29 41 1 0 0 0 0 30 42 1 0 0 0 0 31 35 1 0 0 0 0 31 36 1 1 0 0 0 32 36 1 1 0 0 0 32 38 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 38 1 1 0 0 0 38 7 1 1 0 0 0 39 33 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	602.4
Volume:	657.257
LogP:	7.753
LogD:	5.233
LogS:	-3.543
# Rotatable Bonds:	4
TPSA:	94.83
# H-Bond Aceptor:	5
# H-Bond Donor:	3
# Rings:	6
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.181
Synthetic Accessibility Score:	4.913
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:	-5.426
MDCK Permeability:	1.5920257283141837e-05
Pgp-inhibitor:	0.279
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.031
20% Bioavailability (F20%):	0.01
30% Bioavailability (F30%):	0.935

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.3
Plasma Protein Binding (PPB):	99.28963470458984%
Volume Distribution (VD):	0.442
Pgp-substrate:	1.6006648540496826%

ADMET: Metabolism

CYP1A2-inhibitor:	0.028
CYP1A2-substrate:	0.333
CYP2C19-inhibitor:	0.054
CYP2C19-substrate:	0.379
CYP2C9-inhibitor:	0.183
CYP2C9-substrate:	0.905
CYP2D6-inhibitor:	0.232
CYP2D6-substrate:	0.366
CYP3A4-inhibitor:	0.334
CYP3A4-substrate:	0.267

ADMET: Excretion

Clearance (CL):	4.999
Half-life (T1/2):	0.08

ADMET: Toxicity

hERG Blockers:	0.022
Human Hepatotoxicity (H-HT):	0.44
Drug-inuced Liver Injury (DILI):	0.017
AMES Toxicity:	0.028
Rat Oral Acute Toxicity:	0.173
Maximum Recommended Daily Dose:	0.912
Skin Sensitization:	0.239
Carcinogencity:	0.435
Eye Corrosion:	0.004
Eye Irritation:	0.668
Respiratory Toxicity:	0.965

Download Data

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

Natural Product: NPC43353

Natural Product ID:	NPC43353
*Common Name:**	3-Beta-Caffeoyl-12-Oleanen-28-Oic Acid
IUPAC Name:	(4aS,6aR,6aS,6bR,8aS,10S,12aS,14bS)-10-[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]-2,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylic acid
Synonyms:
Standard InCHIKey:	KFFZENNMYQOFQK-SXXKULMJSA-N
Standard InCHI:	InChI=1S/C39H54O5/c1-34(2)18-20-39(33(43)44)21-19-37(6)25(27(39)23-34)10-13-32-36(5)16-14-26(35(3,4)31(36)15-17-38(32,37)7)28(40)11-8-24-9-12-29(41)30(42)22-24/h8-12,22,26-27,31-32,41-42H,13-21,23H2,1-7H3,(H,43,44)/b11-8+/t26-,27+,31+,32-,36+,37-,38-,39+/m1/s1
SMILES:	O=C([C@H]1CC[C@]2([C@H](C1(C)C)CC[C@@]1([C@@H]2CC=C2[C@@]1(C)CC[C@@]1([C@H]2CC(C)(C)CC1)C(=O)O)C)C)/C=C/c1ccc(c(c1)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL449798
PubChem CID:	44566355
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
NPO6918	Geranium niveum	Species	Geraniaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10346950]
NPO6918	Geranium niveum	Species	Geraniaceae	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
IC50	3

Activity Type	# Activity
Organism	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2645	Organism	Giardia intestinalis	Giardia intestinalis	IC50	=	31.2	ug.mL-1	PMID[533592]
NPT992	Organism	Entamoeba histolytica	Entamoeba histolytica	IC50	=	22.6	ug.mL-1	PMID[533592]
NPT992	Organism	Entamoeba histolytica	Entamoeba histolytica	IC50	=	19.25	ug.mL-1	PMID[533593]

☑ 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 NPC43353 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	334
0.1-0.2	1449
0.2-0.3	2683
0.3-0.4	6988
0.4-0.5	10088
0.5-0.6	11923
0.6-0.7	8358
0.7-0.8	697
0.8-0.85	93
0.85-0.9	69
0.9-0.95	14
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9338	High Similarity	NPC477873
0.9338	High Similarity	NPC469447
0.9254	High Similarity	NPC471152
0.9203	High Similarity	NPC53520
0.9098	High Similarity	NPC475457
0.9098	High Similarity	NPC475627
0.9098	High Similarity	NPC18982
0.9098	High Similarity	NPC475346
0.9091	High Similarity	NPC243305
0.9051	High Similarity	NPC470035
0.9	High Similarity	NPC66894
0.9	High Similarity	NPC8102
0.8955	High Similarity	NPC476282
0.8951	High Similarity	NPC473579
0.8951	High Similarity	NPC475454
0.8951	High Similarity	NPC475311
0.8951	High Similarity	NPC473680
0.8913	High Similarity	NPC304110
0.8913	High Similarity	NPC27518
0.8905	High Similarity	NPC182249
0.8905	High Similarity	NPC471974
0.8905	High Similarity	NPC469681
0.8905	High Similarity	NPC469680
0.8841	High Similarity	NPC473591
0.8841	High Similarity	NPC155192
0.8841	High Similarity	NPC271494
0.8824	High Similarity	NPC173569
0.8824	High Similarity	NPC477874
0.8819	High Similarity	NPC118033
0.8786	High Similarity	NPC184935
0.8759	High Similarity	NPC7464
0.8759	High Similarity	NPC475579
0.8759	High Similarity	NPC473773
0.8759	High Similarity	NPC249817
0.8723	High Similarity	NPC25491
0.8696	High Similarity	NPC277559
0.8696	High Similarity	NPC216940
0.8696	High Similarity	NPC198621
0.8696	High Similarity	NPC475482
0.8696	High Similarity	NPC22676
0.8696	High Similarity	NPC49911
0.8643	High Similarity	NPC473612
0.8633	High Similarity	NPC473779
0.8633	High Similarity	NPC46242
0.8633	High Similarity	NPC297797
0.8633	High Similarity	NPC42384
0.8633	High Similarity	NPC477849
0.8633	High Similarity	NPC157284
0.8633	High Similarity	NPC50615
0.8633	High Similarity	NPC165191
0.8633	High Similarity	NPC245760
0.8633	High Similarity	NPC28592
0.8633	High Similarity	NPC51531
0.8633	High Similarity	NPC289358
0.8633	High Similarity	NPC469857
0.8633	High Similarity	NPC23667
0.8633	High Similarity	NPC473479
0.8633	High Similarity	NPC114333
0.8633	High Similarity	NPC149773
0.8633	High Similarity	NPC5014
0.8633	High Similarity	NPC91887
0.8601	High Similarity	NPC470038
0.8582	High Similarity	NPC35212
0.8571	High Similarity	NPC294330
0.8571	High Similarity	NPC205392
0.8571	High Similarity	NPC105942
0.8561	High Similarity	NPC15127
0.8551	High Similarity	NPC103082
0.8531	High Similarity	NPC307205
0.8527	High Similarity	NPC42657
0.8521	High Similarity	NPC235557
0.8521	High Similarity	NPC252133
0.8521	High Similarity	NPC310621
0.8511	High Similarity	NPC473527
0.8511	High Similarity	NPC172311
0.85	High Similarity	NPC234548
0.85	High Similarity	NPC248287
0.8483	Intermediate Similarity	NPC10842
0.8462	Intermediate Similarity	NPC26045
0.8403	Intermediate Similarity	NPC144247
0.8403	Intermediate Similarity	NPC294679
0.8403	Intermediate Similarity	NPC145301
0.8403	Intermediate Similarity	NPC8493
0.8403	Intermediate Similarity	NPC469375
0.8392	Intermediate Similarity	NPC471971
0.8392	Intermediate Similarity	NPC469855
0.8392	Intermediate Similarity	NPC30846
0.8392	Intermediate Similarity	NPC471972
0.8382	Intermediate Similarity	NPC86257
0.838	Intermediate Similarity	NPC472801
0.8358	Intermediate Similarity	NPC137416
0.8345	Intermediate Similarity	NPC471913
0.8333	Intermediate Similarity	NPC199936
0.8322	Intermediate Similarity	NPC472410
0.8311	Intermediate Similarity	NPC470037
0.8295	Intermediate Similarity	NPC277394
0.8295	Intermediate Similarity	NPC299252
0.8295	Intermediate Similarity	NPC61062
0.8286	Intermediate Similarity	NPC472804
0.8276	Intermediate Similarity	NPC469854
0.8276	Intermediate Similarity	NPC469856
0.8273	Intermediate Similarity	NPC4170
0.8273	Intermediate Similarity	NPC111845
0.8273	Intermediate Similarity	NPC138472
0.8261	Intermediate Similarity	NPC18798
0.8243	Intermediate Similarity	NPC327962
0.8239	Intermediate Similarity	NPC139243
0.8239	Intermediate Similarity	NPC116742
0.8219	Intermediate Similarity	NPC258856
0.8219	Intermediate Similarity	NPC75295
0.8214	Intermediate Similarity	NPC293454
0.8207	Intermediate Similarity	NPC477207
0.8195	Intermediate Similarity	NPC249340
0.8195	Intermediate Similarity	NPC154696
0.8195	Intermediate Similarity	NPC162935
0.8182	Intermediate Similarity	NPC266365
0.8182	Intermediate Similarity	NPC471875
0.8182	Intermediate Similarity	NPC318552
0.8182	Intermediate Similarity	NPC470616
0.8182	Intermediate Similarity	NPC470617
0.8182	Intermediate Similarity	NPC190501
0.8176	Intermediate Similarity	NPC264229
0.8176	Intermediate Similarity	NPC46549
0.8175	Intermediate Similarity	NPC234175
0.8163	Intermediate Similarity	NPC273798
0.8163	Intermediate Similarity	NPC471970
0.8158	Intermediate Similarity	NPC471968
0.8156	Intermediate Similarity	NPC153088
0.8151	Intermediate Similarity	NPC235195
0.8151	Intermediate Similarity	NPC280717
0.8151	Intermediate Similarity	NPC271607
0.8151	Intermediate Similarity	NPC19862
0.8148	Intermediate Similarity	NPC471927
0.8121	Intermediate Similarity	NPC208785
0.8121	Intermediate Similarity	NPC470618
0.8121	Intermediate Similarity	NPC145527
0.8121	Intermediate Similarity	NPC470619
0.812	Intermediate Similarity	NPC259703
0.812	Intermediate Similarity	NPC32322
0.812	Intermediate Similarity	NPC241001
0.8116	Intermediate Similarity	NPC470747
0.8116	Intermediate Similarity	NPC117899
0.8116	Intermediate Similarity	NPC30174
0.8116	Intermediate Similarity	NPC25736
0.8112	Intermediate Similarity	NPC132723
0.8112	Intermediate Similarity	NPC230811
0.8112	Intermediate Similarity	NPC76032
0.8108	Intermediate Similarity	NPC325032
0.8108	Intermediate Similarity	NPC477483
0.8085	Intermediate Similarity	NPC11266
0.8079	Intermediate Similarity	NPC475595
0.8079	Intermediate Similarity	NPC473544
0.8079	Intermediate Similarity	NPC475162
0.8079	Intermediate Similarity	NPC266084
0.8079	Intermediate Similarity	NPC83663
0.8079	Intermediate Similarity	NPC475145
0.8079	Intermediate Similarity	NPC475216
0.8054	Intermediate Similarity	NPC132810
0.8043	Intermediate Similarity	NPC193203
0.8043	Intermediate Similarity	NPC229894
0.8042	Intermediate Similarity	NPC476393
0.8029	Intermediate Similarity	NPC71610
0.8028	Intermediate Similarity	NPC477596
0.8028	Intermediate Similarity	NPC279463
0.8015	Intermediate Similarity	NPC265413
0.8015	Intermediate Similarity	NPC10154
0.8	Intermediate Similarity	NPC121168
0.8	Intermediate Similarity	NPC471853
0.8	Intermediate Similarity	NPC86900
0.8	Intermediate Similarity	NPC476534
0.8	Intermediate Similarity	NPC237441
0.7987	Intermediate Similarity	NPC96930
0.7987	Intermediate Similarity	NPC32017
0.7985	Intermediate Similarity	NPC294361
0.7985	Intermediate Similarity	NPC164852
0.7985	Intermediate Similarity	NPC236520
0.7975	Intermediate Similarity	NPC200726
0.7974	Intermediate Similarity	NPC472807
0.7971	Intermediate Similarity	NPC78364
0.7971	Intermediate Similarity	NPC69424
0.7971	Intermediate Similarity	NPC72667
0.7971	Intermediate Similarity	NPC176130
0.7971	Intermediate Similarity	NPC84672
0.797	Intermediate Similarity	NPC31296
0.797	Intermediate Similarity	NPC473974
0.797	Intermediate Similarity	NPC258366
0.797	Intermediate Similarity	NPC79933
0.7969	Intermediate Similarity	NPC222084
0.7959	Intermediate Similarity	NPC209085
0.7959	Intermediate Similarity	NPC224884
0.7958	Intermediate Similarity	NPC194970
0.7958	Intermediate Similarity	NPC477594
0.7955	Intermediate Similarity	NPC16030
0.7955	Intermediate Similarity	NPC278652
0.7933	Intermediate Similarity	NPC292206
0.7933	Intermediate Similarity	NPC477206
0.7933	Intermediate Similarity	NPC298647
0.7933	Intermediate Similarity	NPC279442
0.7933	Intermediate Similarity	NPC273358
0.7925	Intermediate Similarity	NPC177362

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 NPC43353 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	303
0.1-0.2	893
0.2-0.3	1430
0.3-0.4	2798
0.4-0.5	2262
0.5-0.6	1168
0.6-0.7	278
0.7-0.8	17
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
0.9552	High Similarity	NPD8166	Discontinued
0.8182	Intermediate Similarity	NPD2932	Approved
0.8182	Intermediate Similarity	NPD3019	Approved
0.7872	Intermediate Similarity	NPD6663	Approved
0.7842	Intermediate Similarity	NPD5736	Approved
0.7752	Intermediate Similarity	NPD3021	Approved
0.7752	Intermediate Similarity	NPD3022	Approved
0.7721	Intermediate Similarity	NPD3023	Approved
0.7721	Intermediate Similarity	NPD3026	Approved
0.7704	Intermediate Similarity	NPD3024	Approved
0.7704	Intermediate Similarity	NPD3025	Approved
0.7703	Intermediate Similarity	NPD7003	Approved
0.7647	Intermediate Similarity	NPD7458	Discontinued
0.7551	Intermediate Similarity	NPD5406	Approved
0.7551	Intermediate Similarity	NPD5404	Approved
0.7551	Intermediate Similarity	NPD5405	Approved
0.7551	Intermediate Similarity	NPD5408	Approved
0.75	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD8032	Phase 2
0.75	Intermediate Similarity	NPD8127	Discontinued
0.7372	Intermediate Similarity	NPD7028	Phase 2
0.7365	Intermediate Similarity	NPD3299	Clinical (unspecified phase)
0.7338	Intermediate Similarity	NPD6273	Approved
0.7333	Intermediate Similarity	NPD5951	Approved
0.7324	Intermediate Similarity	NPD1470	Approved
0.731	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7305	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7286	Intermediate Similarity	NPD3092	Approved
0.7286	Intermediate Similarity	NPD1201	Approved
0.7273	Intermediate Similarity	NPD258	Approved
0.7273	Intermediate Similarity	NPD6831	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD257	Approved
0.7266	Intermediate Similarity	NPD7163	Clinical (unspecified phase)
0.7246	Intermediate Similarity	NPD3091	Approved
0.7241	Intermediate Similarity	NPD7095	Approved
0.7237	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7211	Intermediate Similarity	NPD943	Approved
0.7208	Intermediate Similarity	NPD7390	Discontinued
0.7203	Intermediate Similarity	NPD3094	Phase 2
0.7192	Intermediate Similarity	NPD3764	Approved
0.719	Intermediate Similarity	NPD6190	Approved
0.7188	Intermediate Similarity	NPD8438	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD7266	Discontinued
0.7143	Intermediate Similarity	NPD4059	Approved
0.7143	Intermediate Similarity	NPD3300	Phase 2
0.7135	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD1283	Approved
0.7124	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7124	Intermediate Similarity	NPD4110	Phase 3
0.7113	Intermediate Similarity	NPD9269	Phase 2
0.7095	Intermediate Similarity	NPD3620	Phase 2
0.7095	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD826	Approved
0.7095	Intermediate Similarity	NPD825	Approved
0.7078	Intermediate Similarity	NPD7910	Clinical (unspecified phase)
0.7071	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7054	Intermediate Similarity	NPD3020	Approved
0.7021	Intermediate Similarity	NPD3095	Discontinued
0.702	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7013	Intermediate Similarity	NPD4628	Phase 3
0.7006	Intermediate Similarity	NPD7473	Discontinued
0.6987	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6986	Remote Similarity	NPD9569	Approved
0.6978	Remote Similarity	NPD405	Clinical (unspecified phase)
0.6974	Remote Similarity	NPD2935	Discontinued
0.6966	Remote Similarity	NPD1164	Approved
0.6964	Remote Similarity	NPD7228	Approved
0.6957	Remote Similarity	NPD2629	Approved
0.6951	Remote Similarity	NPD6234	Discontinued
0.6933	Remote Similarity	NPD230	Phase 1
0.6933	Remote Similarity	NPD275	Approved
0.6933	Remote Similarity	NPD274	Approved
0.6929	Remote Similarity	NPD7610	Discontinued
0.6923	Remote Similarity	NPD2066	Phase 3
0.6923	Remote Similarity	NPD1281	Approved
0.6919	Remote Similarity	NPD3534	Clinical (unspecified phase)
0.6913	Remote Similarity	NPD259	Phase 1
0.6908	Remote Similarity	NPD2799	Discontinued
0.6908	Remote Similarity	NPD651	Clinical (unspecified phase)
0.6903	Remote Similarity	NPD3750	Approved
0.6901	Remote Similarity	NPD4626	Approved
0.6892	Remote Similarity	NPD7008	Discontinued
0.6892	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD1432	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD3455	Phase 2
0.6867	Remote Similarity	NPD4060	Phase 1
0.6867	Remote Similarity	NPD4140	Approved
0.6852	Remote Similarity	NPD37	Approved
0.6849	Remote Similarity	NPD2797	Approved
0.6846	Remote Similarity	NPD3268	Approved
0.6831	Remote Similarity	NPD9268	Approved
0.6831	Remote Similarity	NPD1651	Approved
0.6829	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6826	Remote Similarity	NPD6232	Discontinued
0.6822	Remote Similarity	NPD2859	Approved
0.6822	Remote Similarity	NPD2860	Approved
0.6821	Remote Similarity	NPD8313	Approved
0.6821	Remote Similarity	NPD6355	Discontinued
0.6821	Remote Similarity	NPD8312	Approved
0.6821	Remote Similarity	NPD555	Phase 2
0.6818	Remote Similarity	NPD2346	Discontinued
0.6815	Remote Similarity	NPD7236	Approved
0.6815	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.6812	Remote Similarity	NPD7094	Approved
0.6812	Remote Similarity	NPD7635	Approved
0.6812	Remote Similarity	NPD6858	Approved
0.6809	Remote Similarity	NPD5536	Phase 2
0.68	Remote Similarity	NPD8150	Discontinued
0.68	Remote Similarity	NPD7961	Discontinued
0.6797	Remote Similarity	NPD5122	Clinical (unspecified phase)
0.679	Remote Similarity	NPD6873	Phase 2
0.6779	Remote Similarity	NPD9536	Phase 1
0.6779	Remote Similarity	NPD9537	Phase 1
0.677	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6767	Remote Similarity	NPD1931	Clinical (unspecified phase)
0.6767	Remote Similarity	NPD1930	Approved
0.6767	Remote Similarity	NPD1929	Approved
0.6763	Remote Similarity	NPD4869	Clinical (unspecified phase)
0.6759	Remote Similarity	NPD3972	Approved
0.6757	Remote Similarity	NPD9494	Approved
0.6755	Remote Similarity	NPD2979	Phase 3
0.6753	Remote Similarity	NPD6099	Approved
0.6753	Remote Similarity	NPD6100	Approved
0.6744	Remote Similarity	NPD2934	Approved
0.6744	Remote Similarity	NPD2933	Approved
0.6744	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6733	Remote Similarity	NPD6798	Discontinued
0.6732	Remote Similarity	NPD7097	Phase 1
0.6731	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.673	Remote Similarity	NPD4160	Clinical (unspecified phase)
0.6727	Remote Similarity	NPD7768	Phase 2
0.6727	Remote Similarity	NPD4966	Approved
0.6727	Remote Similarity	NPD4965	Approved
0.6727	Remote Similarity	NPD4967	Phase 2
0.6725	Remote Similarity	NPD5844	Phase 1
0.6713	Remote Similarity	NPD4093	Discontinued
0.6712	Remote Similarity	NPD1755	Approved
0.6711	Remote Similarity	NPD2605	Approved
0.6711	Remote Similarity	NPD2606	Approved
0.6707	Remote Similarity	NPD7819	Suspended
0.6707	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6691	Remote Similarity	NPD2342	Discontinued
0.6689	Remote Similarity	NPD2798	Approved
0.6667	Remote Similarity	NPD255	Approved
0.6667	Remote Similarity	NPD3226	Approved
0.6667	Remote Similarity	NPD5156	Approved
0.6667	Remote Similarity	NPD4198	Discontinued
0.6667	Remote Similarity	NPD256	Approved
0.6667	Remote Similarity	NPD5155	Approved
0.6667	Remote Similarity	NPD1751	Approved
0.6646	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6645	Remote Similarity	NPD6346	Approved
0.6645	Remote Similarity	NPD2438	Suspended
0.6644	Remote Similarity	NPD4878	Approved
0.6644	Remote Similarity	NPD1608	Approved
0.6643	Remote Similarity	NPD5283	Phase 1
0.6643	Remote Similarity	NPD9545	Approved
0.6641	Remote Similarity	NPD288	Approved
0.6625	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6619	Remote Similarity	NPD228	Approved
0.6617	Remote Similarity	NPD289	Clinical (unspecified phase)
0.6609	Remote Similarity	NPD7685	Pre-registration
0.6606	Remote Similarity	NPD1465	Phase 2
0.6605	Remote Similarity	NPD7239	Suspended
0.6601	Remote Similarity	NPD5735	Approved
0.66	Remote Similarity	NPD3595	Approved
0.66	Remote Similarity	NPD3594	Approved
0.6597	Remote Similarity	NPD5691	Approved
0.6594	Remote Similarity	NPD4750	Phase 3
0.6593	Remote Similarity	NPD5909	Discontinued
0.6585	Remote Similarity	NPD6677	Suspended
0.6581	Remote Similarity	NPD7743	Approved
0.6581	Remote Similarity	NPD7742	Approved
0.6581	Remote Similarity	NPD3748	Approved
0.6579	Remote Similarity	NPD7714	Approved
0.6579	Remote Similarity	NPD7715	Approved
0.6579	Remote Similarity	NPD6233	Phase 2
0.6577	Remote Similarity	NPD4624	Approved
0.6565	Remote Similarity	NPD844	Approved
0.6565	Remote Similarity	NPD1809	Phase 2
0.6562	Remote Similarity	NPD1511	Approved
0.6556	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6554	Remote Similarity	NPD1876	Approved
0.6552	Remote Similarity	NPD2286	Discontinued
0.655	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.655	Remote Similarity	NPD6166	Phase 2
0.655	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.655	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6547	Remote Similarity	NPD4141	Clinical (unspecified phase)
0.6545	Remote Similarity	NPD1934	Approved
0.6541	Remote Similarity	NPD8131	Suspended
0.6538	Remote Similarity	NPD9570	Approved
0.6538	Remote Similarity	NPD2531	Phase 2
0.6533	Remote Similarity	NPD3635	Approved
0.6533	Remote Similarity	NPD3637	Approved
0.6533	Remote Similarity	NPD3636	Approved
0.6522	Remote Similarity	NPD3645	Discontinued
0.6522	Remote Similarity	NPD74	Approved
0.6522	Remote Similarity	NPD9266	Approved
0.6517	Remote Similarity	NPD8434	Phase 2

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