NPASS Compound

Structure

NPC24504 OpenBabel07101719242D 23 26 0 0 1 0 0 0 0 0999 V2000 -1.4576 2.1380 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3709 0.2141 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8709 1.0801 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2424 1.5801 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2472 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2472 2.1603 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6236 1.8002 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6236 -0.3600 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2650 1.0088 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9195 -0.3930 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0646 1.2185 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5775 0.3600 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.5630 1.1691 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.2472 0.7201 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.8709 1.8002 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 0.7201 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0896 0.9960 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.8709 1.0801 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6236 1.0801 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 -0.3405 2.1440 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.7369 2.3002 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.6634 1.6539 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 11 2 0 0 0 0 2 18 1 0 0 0 0 3 18 1 0 0 0 0 5 8 1 0 0 0 0 5 14 1 0 0 0 0 6 7 1 0 0 0 0 6 15 1 0 0 0 0 7 19 1 0 0 0 0 9 13 1 0 0 0 0 10 12 1 0 0 0 0 10 20 1 0 0 0 0 11 12 1 0 0 0 0 11 17 1 0 0 0 0 12 9 1 1 0 0 0 13 16 1 0 0 0 0 13 21 1 6 0 0 0 14 18 1 0 0 0 0 14 19 1 1 0 0 0 15 18 1 0 0 0 0 15 22 1 6 0 0 0 16 19 1 1 0 0 0 16 20 1 0 0 0 0 17 20 1 1 0 0 0 17 23 1 0 0 0 0 19 4 1 1 0 0 0 20 8 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	320.24
Volume:	343.985
LogP:	2.513
LogD:	3.26
LogS:	-3.367
# Rotatable Bonds:	0
TPSA:	60.69
# H-Bond Aceptor:	3
# H-Bond Donor:	3
# Rings:	4
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.602
Synthetic Accessibility Score:	5.867
Fsp3:	0.9
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.793
MDCK Permeability:	1.567458821227774e-05
Pgp-inhibitor:	0.002
Pgp-substrate:	0.997
Human Intestinal Absorption (HIA):	0.011
20% Bioavailability (F20%):	0.796
30% Bioavailability (F30%):	0.446

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.744
Plasma Protein Binding (PPB):	38.77199172973633%
Volume Distribution (VD):	1.498
Pgp-substrate:	62.36907958984375%

ADMET: Metabolism

CYP1A2-inhibitor:	0.026
CYP1A2-substrate:	0.119
CYP2C19-inhibitor:	0.012
CYP2C19-substrate:	0.669
CYP2C9-inhibitor:	0.02
CYP2C9-substrate:	0.074
CYP2D6-inhibitor:	0.005
CYP2D6-substrate:	0.175
CYP3A4-inhibitor:	0.174
CYP3A4-substrate:	0.154

ADMET: Excretion

Clearance (CL):	8.683
Half-life (T1/2):	0.218

ADMET: Toxicity

hERG Blockers:	0.084
Human Hepatotoxicity (H-HT):	0.32
Drug-inuced Liver Injury (DILI):	0.035
AMES Toxicity:	0.021
Rat Oral Acute Toxicity:	0.989
Maximum Recommended Daily Dose:	0.998
Skin Sensitization:	0.751
Carcinogencity:	0.642
Eye Corrosion:	0.58
Eye Irritation:	0.505
Respiratory Toxicity:	0.972

Download Data

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

Natural Product: NPC24504

Natural Product ID:	NPC24504
*Common Name:**	Tenuifolin B
IUPAC Name:	n.a.
Synonyms:	Tenuifolin B
Standard InCHIKey:	MQWPDQKLLPDSQK-MJWYYFFNSA-N
Standard InCHI:	InChI=1S/C20H32O3/c1-11-12-9-13(21)16-19(4)7-6-15(22)18(2,3)14(19)5-8-20(16,10-12)17(11)23/h12-17,21-23H,1,5-10H2,2-4H3/t12-,13+,14-,15+,16+,17-,19-,20-/m1/s1
SMILES:	O[C@H]1C[C@@H]2C[C@]3([C@@H]1[C@]1(C)CC[C@@H](C([C@H]1CC3)(C)C)O)[C@@H](C2=C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2334475
PubChem CID:	71579049
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0003782] Kaurane diterpenoids

*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
NPO33364	isodon tenuifolius	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23327668]
NPO33364	isodon tenuifolius	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25375202]

☑ 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	6

Activity Type	# Activity
Cell Line	6

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	>	25000.0	nM	PMID[549723]
NPT660	Cell Line	SW480	Homo sapiens	IC50	>	10000.0	nM	PMID[549723]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	>	10000.0	nM	PMID[549723]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	10000.0	nM	PMID[549723]
NPT659	Cell Line	SMMC-7721	Homo sapiens	IC50	>	10000.0	nM	PMID[549723]
NPT116	Cell Line	HL-60	Homo sapiens	IC50	>	10000.0	nM	PMID[549723]

☑ 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 NPC24504 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	172
0.1-0.2	2038
0.2-0.3	8239
0.3-0.4	15542
0.4-0.5	6353
0.5-0.6	4986
0.6-0.7	4011
0.7-0.8	1141
0.8-0.85	118
0.85-0.9	63
0.9-0.95	22
0.95-1	12

Similarity Score	Similarity Level	Natural Product ID
0.9865	High Similarity	NPC47149
0.9863	High Similarity	NPC472500
0.9863	High Similarity	NPC472502
0.9863	High Similarity	NPC472499
0.9863	High Similarity	NPC475
0.973	High Similarity	NPC476316
0.9726	High Similarity	NPC138502
0.9595	High Similarity	NPC477817
0.9595	High Similarity	NPC477819
0.9589	High Similarity	NPC38141
0.9459	High Similarity	NPC307336
0.9459	High Similarity	NPC260301
0.9359	High Similarity	NPC256567
0.9342	High Similarity	NPC71535
0.9342	High Similarity	NPC78545
0.9333	High Similarity	NPC472501
0.9315	High Similarity	NPC308440
0.9315	High Similarity	NPC472503
0.9221	High Similarity	NPC157655
0.9211	High Similarity	NPC5604
0.9189	High Similarity	NPC185536
0.9178	High Similarity	NPC472506
0.9079	High Similarity	NPC301707
0.9054	High Similarity	NPC476736
0.9041	High Similarity	NPC164045
0.8987	High Similarity	NPC477818
0.8987	High Similarity	NPC232023
0.8987	High Similarity	NPC110778
0.8947	High Similarity	NPC331618
0.8947	High Similarity	NPC248830
0.8947	High Similarity	NPC212241
0.8947	High Similarity	NPC257191
0.8947	High Similarity	NPC119355
0.8947	High Similarity	NPC202540
0.8933	High Similarity	NPC3403
0.8904	High Similarity	NPC45296
0.8902	High Similarity	NPC160304
0.8889	High Similarity	NPC139724
0.8875	High Similarity	NPC255882
0.8846	High Similarity	NPC475679
0.8831	High Similarity	NPC472342
0.8831	High Similarity	NPC31828
0.8831	High Similarity	NPC42853
0.8816	High Similarity	NPC86305
0.8816	High Similarity	NPC14112
0.8784	High Similarity	NPC111234
0.875	High Similarity	NPC141941
0.875	High Similarity	NPC193870
0.8718	High Similarity	NPC49627
0.8718	High Similarity	NPC475727
0.8718	High Similarity	NPC116119
0.8718	High Similarity	NPC80297
0.8718	High Similarity	NPC49599
0.8718	High Similarity	NPC472742
0.869	High Similarity	NPC219937
0.869	High Similarity	NPC194485
0.869	High Similarity	NPC123252
0.869	High Similarity	NPC53890
0.8684	High Similarity	NPC240235
0.8684	High Similarity	NPC230704
0.8684	High Similarity	NPC103822
0.8684	High Similarity	NPC178383
0.8684	High Similarity	NPC212879
0.8684	High Similarity	NPC231256
0.8684	High Similarity	NPC104387
0.8684	High Similarity	NPC70982
0.8659	High Similarity	NPC24277
0.8659	High Similarity	NPC121981
0.8659	High Similarity	NPC201273
0.8642	High Similarity	NPC209802
0.8642	High Similarity	NPC475798
0.8642	High Similarity	NPC127606
0.8642	High Similarity	NPC124172
0.859	High Similarity	NPC167037
0.859	High Similarity	NPC244385
0.859	High Similarity	NPC138621
0.859	High Similarity	NPC6978
0.8571	High Similarity	NPC78067
0.8571	High Similarity	NPC91573
0.8571	High Similarity	NPC93662
0.8571	High Similarity	NPC278091
0.8553	High Similarity	NPC192638
0.8553	High Similarity	NPC49168
0.8553	High Similarity	NPC254509
0.8553	High Similarity	NPC62657
0.8553	High Similarity	NPC196358
0.8553	High Similarity	NPC145552
0.8553	High Similarity	NPC5046
0.8553	High Similarity	NPC25511
0.8519	High Similarity	NPC85095
0.8519	High Similarity	NPC470929
0.8519	High Similarity	NPC211135
0.8519	High Similarity	NPC216420
0.8514	High Similarity	NPC477820
0.8488	Intermediate Similarity	NPC26046
0.8481	Intermediate Similarity	NPC1319
0.8481	Intermediate Similarity	NPC273410
0.8481	Intermediate Similarity	NPC80530
0.8471	Intermediate Similarity	NPC100313
0.8442	Intermediate Similarity	NPC144075
0.8442	Intermediate Similarity	NPC200243
0.8434	Intermediate Similarity	NPC6605
0.8421	Intermediate Similarity	NPC195489
0.8415	Intermediate Similarity	NPC86238
0.84	Intermediate Similarity	NPC232925
0.84	Intermediate Similarity	NPC251201
0.84	Intermediate Similarity	NPC63588
0.8395	Intermediate Similarity	NPC470614
0.8395	Intermediate Similarity	NPC296701
0.8395	Intermediate Similarity	NPC1272
0.8395	Intermediate Similarity	NPC218616
0.8395	Intermediate Similarity	NPC472504
0.8378	Intermediate Similarity	NPC245795
0.8375	Intermediate Similarity	NPC322313
0.8375	Intermediate Similarity	NPC236237
0.8375	Intermediate Similarity	NPC102253
0.8375	Intermediate Similarity	NPC26117
0.8372	Intermediate Similarity	NPC130840
0.8354	Intermediate Similarity	NPC285761
0.8354	Intermediate Similarity	NPC102708
0.8353	Intermediate Similarity	NPC105495
0.8333	Intermediate Similarity	NPC237460
0.8333	Intermediate Similarity	NPC472495
0.8333	Intermediate Similarity	NPC474657
0.8333	Intermediate Similarity	NPC186145
0.8295	Intermediate Similarity	NPC241047
0.8293	Intermediate Similarity	NPC113978
0.8272	Intermediate Similarity	NPC209620
0.8272	Intermediate Similarity	NPC476646
0.8272	Intermediate Similarity	NPC23852
0.825	Intermediate Similarity	NPC472463
0.825	Intermediate Similarity	NPC30986
0.825	Intermediate Similarity	NPC209430
0.8243	Intermediate Similarity	NPC269077
0.8243	Intermediate Similarity	NPC253303
0.8235	Intermediate Similarity	NPC475664
0.8235	Intermediate Similarity	NPC470542
0.8235	Intermediate Similarity	NPC133588
0.8235	Intermediate Similarity	NPC471952
0.8228	Intermediate Similarity	NPC470711
0.8228	Intermediate Similarity	NPC470758
0.8219	Intermediate Similarity	NPC27243
0.8219	Intermediate Similarity	NPC476737
0.8214	Intermediate Similarity	NPC261266
0.8214	Intermediate Similarity	NPC152808
0.8214	Intermediate Similarity	NPC6391
0.8214	Intermediate Similarity	NPC293287
0.8214	Intermediate Similarity	NPC299068
0.8202	Intermediate Similarity	NPC306797
0.8202	Intermediate Similarity	NPC169270
0.8202	Intermediate Similarity	NPC292718
0.8202	Intermediate Similarity	NPC111834
0.8193	Intermediate Similarity	NPC299963
0.8182	Intermediate Similarity	NPC470610
0.8182	Intermediate Similarity	NPC211009
0.8182	Intermediate Similarity	NPC280804
0.8182	Intermediate Similarity	NPC3359
0.8171	Intermediate Similarity	NPC50964
0.8171	Intermediate Similarity	NPC248886
0.8158	Intermediate Similarity	NPC283316
0.8148	Intermediate Similarity	NPC96362
0.8148	Intermediate Similarity	NPC13554
0.814	Intermediate Similarity	NPC109744
0.814	Intermediate Similarity	NPC74258
0.814	Intermediate Similarity	NPC470361
0.8125	Intermediate Similarity	NPC474216
0.8125	Intermediate Similarity	NPC302041
0.8125	Intermediate Similarity	NPC11908
0.8125	Intermediate Similarity	NPC477514
0.8125	Intermediate Similarity	NPC65897
0.8125	Intermediate Similarity	NPC477522
0.8125	Intermediate Similarity	NPC85346
0.8125	Intermediate Similarity	NPC87604
0.8118	Intermediate Similarity	NPC470620
0.8118	Intermediate Similarity	NPC472497
0.8108	Intermediate Similarity	NPC44122
0.8101	Intermediate Similarity	NPC470749
0.8101	Intermediate Similarity	NPC63958
0.8101	Intermediate Similarity	NPC189883
0.8101	Intermediate Similarity	NPC73875
0.8095	Intermediate Similarity	NPC318390
0.8095	Intermediate Similarity	NPC292553
0.8095	Intermediate Similarity	NPC164424
0.8095	Intermediate Similarity	NPC470360
0.809	Intermediate Similarity	NPC30477
0.8082	Intermediate Similarity	NPC68656
0.8077	Intermediate Similarity	NPC469533
0.8077	Intermediate Similarity	NPC48795
0.8077	Intermediate Similarity	NPC469593
0.8077	Intermediate Similarity	NPC306727
0.8077	Intermediate Similarity	NPC304499
0.8077	Intermediate Similarity	NPC469534
0.8072	Intermediate Similarity	NPC207013
0.8072	Intermediate Similarity	NPC82623
0.8068	Intermediate Similarity	NPC296620
0.8052	Intermediate Similarity	NPC301226
0.8049	Intermediate Similarity	NPC470383
0.8046	Intermediate Similarity	NPC329596
0.8046	Intermediate Similarity	NPC204188
0.8046	Intermediate Similarity	NPC475751

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 NPC24504 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	170
0.1-0.2	2384
0.2-0.3	4371
0.3-0.4	1563
0.4-0.5	272
0.5-0.6	168
0.6-0.7	179
0.7-0.8	42
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8375	Intermediate Similarity	NPD7525	Registered
0.7907	Intermediate Similarity	NPD4751	Clinical (unspecified phase)
0.7875	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.775	Intermediate Similarity	NPD6942	Approved
0.775	Intermediate Similarity	NPD7339	Approved
0.7674	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.759	Intermediate Similarity	NPD7645	Phase 2
0.759	Intermediate Similarity	NPD6929	Approved
0.75	Intermediate Similarity	NPD6931	Approved
0.75	Intermediate Similarity	NPD6930	Phase 2
0.7468	Intermediate Similarity	NPD4787	Phase 1
0.7442	Intermediate Similarity	NPD4788	Approved
0.7375	Intermediate Similarity	NPD4243	Approved
0.7368	Intermediate Similarity	NPD7639	Approved
0.7368	Intermediate Similarity	NPD7640	Approved
0.7356	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.7349	Intermediate Similarity	NPD6925	Approved
0.7349	Intermediate Similarity	NPD5776	Phase 2
0.7342	Intermediate Similarity	NPD4267	Clinical (unspecified phase)
0.7294	Intermediate Similarity	NPD4748	Discontinued
0.7294	Intermediate Similarity	NPD6928	Phase 2
0.7283	Intermediate Similarity	NPD4202	Approved
0.7263	Intermediate Similarity	NPD7638	Approved
0.7262	Intermediate Similarity	NPD7145	Approved
0.7241	Intermediate Similarity	NPD6695	Phase 3
0.7195	Intermediate Similarity	NPD4785	Approved
0.7195	Intermediate Similarity	NPD4784	Approved
0.7195	Intermediate Similarity	NPD6924	Approved
0.7195	Intermediate Similarity	NPD6926	Approved
0.7174	Intermediate Similarity	NPD8035	Phase 2
0.7174	Intermediate Similarity	NPD8034	Phase 2
0.7159	Intermediate Similarity	NPD4786	Approved
0.7143	Intermediate Similarity	NPD5328	Approved
0.7093	Intermediate Similarity	NPD7514	Phase 3
0.7079	Intermediate Similarity	NPD6893	Approved
0.7059	Intermediate Similarity	NPD6114	Approved
0.7059	Intermediate Similarity	NPD6697	Approved
0.7059	Intermediate Similarity	NPD6115	Approved
0.7059	Intermediate Similarity	NPD6118	Approved
0.7041	Intermediate Similarity	NPD5211	Phase 2
0.7024	Intermediate Similarity	NPD6933	Approved
0.7011	Intermediate Similarity	NPD6902	Approved
0.7	Intermediate Similarity	NPD3618	Phase 1
0.6989	Remote Similarity	NPD6079	Approved
0.6979	Remote Similarity	NPD4755	Approved
0.6966	Remote Similarity	NPD3665	Phase 1
0.6966	Remote Similarity	NPD3666	Approved
0.6966	Remote Similarity	NPD3133	Approved
0.6951	Remote Similarity	NPD7152	Approved
0.6951	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6951	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6951	Remote Similarity	NPD7150	Approved
0.6951	Remote Similarity	NPD7151	Approved
0.6941	Remote Similarity	NPD6116	Phase 1
0.6941	Remote Similarity	NPD6932	Approved
0.6932	Remote Similarity	NPD3667	Approved
0.6923	Remote Similarity	NPD7524	Approved
0.6923	Remote Similarity	NPD7750	Discontinued
0.6914	Remote Similarity	NPD6923	Approved
0.6914	Remote Similarity	NPD6922	Approved
0.6905	Remote Similarity	NPD3703	Phase 2
0.6905	Remote Similarity	NPD4190	Phase 3
0.6905	Remote Similarity	NPD5275	Approved
0.69	Remote Similarity	NPD5141	Approved
0.6897	Remote Similarity	NPD7332	Phase 2
0.6897	Remote Similarity	NPD7509	Discontinued
0.6869	Remote Similarity	NPD7632	Discontinued
0.6837	Remote Similarity	NPD4696	Approved
0.6837	Remote Similarity	NPD5286	Approved
0.6837	Remote Similarity	NPD4700	Approved
0.6837	Remote Similarity	NPD5285	Approved
0.6829	Remote Similarity	NPD7144	Approved
0.6829	Remote Similarity	NPD7143	Approved
0.6829	Remote Similarity	NPD4245	Approved
0.6829	Remote Similarity	NPD4244	Approved
0.6824	Remote Similarity	NPD6117	Approved
0.6818	Remote Similarity	NPD6898	Phase 1
0.6786	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6782	Remote Similarity	NPD4195	Approved
0.6782	Remote Similarity	NPD6683	Phase 2
0.6768	Remote Similarity	NPD5223	Approved
0.6707	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6707	Remote Similarity	NPD3698	Phase 2
0.6707	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6706	Remote Similarity	NPD8264	Approved
0.67	Remote Similarity	NPD4633	Approved
0.67	Remote Similarity	NPD5225	Approved
0.67	Remote Similarity	NPD5226	Approved
0.67	Remote Similarity	NPD5224	Approved
0.6667	Remote Similarity	NPD7128	Approved
0.6667	Remote Similarity	NPD5739	Approved
0.6667	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6675	Approved
0.6667	Remote Similarity	NPD6402	Approved
0.6634	Remote Similarity	NPD5174	Approved
0.6634	Remote Similarity	NPD5175	Approved
0.6634	Remote Similarity	NPD4754	Approved
0.6632	Remote Similarity	NPD7515	Phase 2
0.6632	Remote Similarity	NPD7087	Discontinued
0.6606	Remote Similarity	NPD7328	Approved
0.6606	Remote Similarity	NPD7327	Approved
0.6596	Remote Similarity	NPD4753	Phase 2
0.6571	Remote Similarity	NPD4634	Approved
0.6562	Remote Similarity	NPD6399	Phase 3
0.6556	Remote Similarity	NPD4221	Approved
0.6556	Remote Similarity	NPD4223	Phase 3
0.6545	Remote Similarity	NPD7516	Approved
0.6542	Remote Similarity	NPD8133	Approved
0.6538	Remote Similarity	NPD6881	Approved
0.6538	Remote Similarity	NPD6899	Approved
0.6538	Remote Similarity	NPD7320	Approved
0.6531	Remote Similarity	NPD4697	Phase 3
0.6531	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6531	Remote Similarity	NPD5222	Approved
0.6531	Remote Similarity	NPD5221	Approved
0.6522	Remote Similarity	NPD5329	Approved
0.6505	Remote Similarity	NPD4767	Approved
0.6505	Remote Similarity	NPD4768	Approved
0.6486	Remote Similarity	NPD8294	Approved
0.6486	Remote Similarity	NPD8377	Approved
0.6476	Remote Similarity	NPD6372	Approved
0.6476	Remote Similarity	NPD6373	Approved
0.6465	Remote Similarity	NPD5173	Approved
0.6442	Remote Similarity	NPD5697	Approved
0.6442	Remote Similarity	NPD5701	Approved
0.6429	Remote Similarity	NPD8380	Approved
0.6429	Remote Similarity	NPD8378	Approved
0.6429	Remote Similarity	NPD8033	Approved
0.6429	Remote Similarity	NPD8335	Approved
0.6429	Remote Similarity	NPD8379	Approved
0.6429	Remote Similarity	NPD4789	Approved
0.6429	Remote Similarity	NPD8296	Approved
0.6421	Remote Similarity	NPD6051	Approved
0.6415	Remote Similarity	NPD7290	Approved
0.6415	Remote Similarity	NPD7102	Approved
0.6415	Remote Similarity	NPD6883	Approved
0.6413	Remote Similarity	NPD4197	Approved
0.6392	Remote Similarity	NPD8171	Discontinued
0.6389	Remote Similarity	NPD4632	Approved
0.6386	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.6386	Remote Similarity	NPD5360	Phase 3
0.6381	Remote Similarity	NPD5128	Approved
0.6381	Remote Similarity	NPD4730	Approved
0.6381	Remote Similarity	NPD6011	Approved
0.6381	Remote Similarity	NPD4729	Approved
0.6355	Remote Similarity	NPD6847	Approved
0.6355	Remote Similarity	NPD6649	Approved
0.6355	Remote Similarity	NPD6869	Approved
0.6355	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6355	Remote Similarity	NPD6617	Approved
0.6355	Remote Similarity	NPD6650	Approved
0.6355	Remote Similarity	NPD8130	Phase 1
0.6327	Remote Similarity	NPD7748	Approved
0.6321	Remote Similarity	NPD6012	Approved
0.6321	Remote Similarity	NPD6013	Approved
0.6321	Remote Similarity	NPD6014	Approved
0.6316	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.63	Remote Similarity	NPD6083	Phase 2
0.63	Remote Similarity	NPD6084	Phase 2
0.63	Remote Similarity	NPD7902	Approved
0.6296	Remote Similarity	NPD6882	Approved
0.6296	Remote Similarity	NPD8297	Approved
0.6289	Remote Similarity	NPD7637	Suspended
0.6286	Remote Similarity	NPD6412	Phase 2
0.6277	Remote Similarity	NPD4688	Approved
0.6277	Remote Similarity	NPD7146	Approved
0.6277	Remote Similarity	NPD4690	Approved
0.6277	Remote Similarity	NPD6684	Approved
0.6277	Remote Similarity	NPD4138	Approved
0.6277	Remote Similarity	NPD5205	Approved
0.6277	Remote Similarity	NPD5330	Approved
0.6277	Remote Similarity	NPD4693	Phase 3
0.6277	Remote Similarity	NPD7521	Approved
0.6277	Remote Similarity	NPD6409	Approved
0.6277	Remote Similarity	NPD7334	Approved
0.6277	Remote Similarity	NPD4689	Approved
0.6277	Remote Similarity	NPD5279	Phase 3
0.6275	Remote Similarity	NPD4159	Approved
0.6263	Remote Similarity	NPD4629	Approved
0.6263	Remote Similarity	NPD5210	Approved
0.6262	Remote Similarity	NPD5250	Approved
0.6262	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6262	Remote Similarity	NPD5248	Approved
0.6262	Remote Similarity	NPD5251	Approved
0.6262	Remote Similarity	NPD5249	Phase 3
0.6262	Remote Similarity	NPD5247	Approved
0.6262	Remote Similarity	NPD5169	Approved
0.6262	Remote Similarity	NPD5135	Approved
0.625	Remote Similarity	NPD368	Approved
0.6238	Remote Similarity	NPD5290	Discontinued
0.6237	Remote Similarity	NPD3668	Phase 3
0.622	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.6216	Remote Similarity	NPD6009	Approved
0.6207	Remote Similarity	NPD7507	Approved
0.6204	Remote Similarity	NPD5216	Approved
0.6204	Remote Similarity	NPD5215	Approved
0.6204	Remote Similarity	NPD5217	Approved
0.6204	Remote Similarity	NPD5127	Approved
0.6195	Remote Similarity	NPD6059	Approved
0.6195	Remote Similarity	NPD6054	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