NPASS Compound

Structure

NPC235792 OpenBabel07101718182D 21 23 0 0 1 0 0 0 0 0999 V2000 -3.0533 -1.5932 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2704 2.5734 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0261 3.1233 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4585 2.4848 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2389 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6320 0.9195 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6195 -0.6922 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1195 1.4985 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6195 -0.6922 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3600 1.5775 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4505 2.3055 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2430 0.0896 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2185 1.0646 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.0204 1.0646 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.9960 0.0896 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.3930 0.9195 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8789 1.5775 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.8708 1.3982 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3680 1.1420 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.4545 2.3952 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 9 1 0 0 0 0 2 10 2 0 0 0 0 3 11 1 0 0 0 0 5 6 1 0 0 0 0 5 12 1 0 0 0 0 6 17 1 0 0 0 0 7 9 1 0 0 0 0 8 14 1 0 0 0 0 9 12 2 0 0 0 0 10 13 1 0 0 0 0 10 16 1 0 0 0 0 11 18 2 0 0 0 0 11 21 1 0 0 0 0 12 14 1 0 0 0 0 13 8 1 6 0 0 0 13 15 1 0 0 0 0 14 17 1 6 0 0 0 15 7 1 6 0 0 0 15 20 1 0 0 0 0 16 19 2 0 0 0 0 16 20 1 0 0 0 0 17 4 1 6 0 0 0 17 21 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	290.15
Volume:	301.534
LogP:	2.536
LogD:	1.775
LogS:	-3.374
# Rotatable Bonds:	2
TPSA:	52.6
# H-Bond Aceptor:	4
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.423
Synthetic Accessibility Score:	4.514
Fsp3:	0.647
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	2
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.705
MDCK Permeability:	3.5021628718823195e-05
Pgp-inhibitor:	0.027
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.012
20% Bioavailability (F20%):	0.067
30% Bioavailability (F30%):	0.515

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.018
Plasma Protein Binding (PPB):	86.88288116455078%
Volume Distribution (VD):	2.472
Pgp-substrate:	8.894244194030762%

ADMET: Metabolism

CYP1A2-inhibitor:	0.153
CYP1A2-substrate:	0.086
CYP2C19-inhibitor:	0.248
CYP2C19-substrate:	0.3
CYP2C9-inhibitor:	0.412
CYP2C9-substrate:	0.095
CYP2D6-inhibitor:	0.018
CYP2D6-substrate:	0.161
CYP3A4-inhibitor:	0.417
CYP3A4-substrate:	0.286

ADMET: Excretion

Clearance (CL):	4.864
Half-life (T1/2):	0.528

ADMET: Toxicity

hERG Blockers:	0.014
Human Hepatotoxicity (H-HT):	0.784
Drug-inuced Liver Injury (DILI):	0.871
AMES Toxicity:	0.052
Rat Oral Acute Toxicity:	0.165
Maximum Recommended Daily Dose:	0.524
Skin Sensitization:	0.921
Carcinogencity:	0.374
Eye Corrosion:	0.138
Eye Irritation:	0.676
Respiratory Toxicity:	0.86

Download Data

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

Natural Product: NPC235792

Natural Product ID:	NPC235792
*Common Name:**	ZEINZRBCJRVISK-KCYZZUKISA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	ZEINZRBCJRVISK-KCYZZUKISA-N
Standard InCHI:	InChI=1S/C17H22O4/c1-9-7-15-13(10(2)16(19)20-15)8-14-12(9)5-6-17(14,4)21-11(3)18/h13-15H,2,5-8H2,1,3-4H3/t13-,14-,15-,17-/m1/s1
SMILES:	CC1=C2CC[C@](C)([C@@H]2C[C@@H]2C(=C)C(=O)O[C@@H]2C1)OC(=O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3593385
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000050] Lactones [CHEMONTID:0001245] Gamma butyrolactones

*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
NPO33441	leucophyta brownii	Species	Asteraceae	Eukaryota	Resinous Exudates	n.a.	n.a.	PMID[26218649]

☑ 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	4

Activity Type	# Activity
Cell Line	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	8000.0	nM	PMID[529705]
NPT139	Cell Line	HT-29	Homo sapiens	IC50	=	4800.0	nM	PMID[529705]
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	2600.0	nM	PMID[529705]
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	3500.0	nM	PMID[529705]

☑ 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 NPC235792 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	225
0.1-0.2	1527
0.2-0.3	6144
0.3-0.4	15384
0.4-0.5	9401
0.5-0.6	6658
0.6-0.7	2622
0.7-0.8	619
0.8-0.85	96
0.85-0.9	16
0.9-0.95	4
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.939	High Similarity	NPC67493
0.9167	High Similarity	NPC224652
0.908	High Similarity	NPC127019
0.9	High Similarity	NPC182550
0.8977	High Similarity	NPC67584
0.8977	High Similarity	NPC213698
0.8953	High Similarity	NPC37607
0.8953	High Similarity	NPC301969
0.8916	High Similarity	NPC156485
0.8902	High Similarity	NPC246076
0.8876	High Similarity	NPC213078
0.8778	High Similarity	NPC161493
0.8764	High Similarity	NPC52044
0.8764	High Similarity	NPC224689
0.8764	High Similarity	NPC170120
0.875	High Similarity	NPC470240
0.875	High Similarity	NPC476794
0.8706	High Similarity	NPC64153
0.8636	High Similarity	NPC133698
0.8621	High Similarity	NPC472872
0.8605	High Similarity	NPC24728
0.8588	High Similarity	NPC300082
0.8588	High Similarity	NPC204105
0.8588	High Similarity	NPC284534
0.8571	High Similarity	NPC318468
0.8506	High Similarity	NPC91248
0.8506	High Similarity	NPC471149
0.8506	High Similarity	NPC79549
0.8495	Intermediate Similarity	NPC150923
0.8488	Intermediate Similarity	NPC107787
0.8488	Intermediate Similarity	NPC304558
0.8478	Intermediate Similarity	NPC221615
0.8471	Intermediate Similarity	NPC115786
0.8444	Intermediate Similarity	NPC477131
0.8444	Intermediate Similarity	NPC198853
0.8434	Intermediate Similarity	NPC74673
0.8434	Intermediate Similarity	NPC302426
0.8434	Intermediate Similarity	NPC276356
0.8434	Intermediate Similarity	NPC69271
0.8427	Intermediate Similarity	NPC131209
0.8409	Intermediate Similarity	NPC283409
0.8409	Intermediate Similarity	NPC215556
0.8409	Intermediate Similarity	NPC4986
0.8391	Intermediate Similarity	NPC270270
0.8391	Intermediate Similarity	NPC475703
0.8391	Intermediate Similarity	NPC118601
0.8375	Intermediate Similarity	NPC143979
0.8375	Intermediate Similarity	NPC320537
0.8372	Intermediate Similarity	NPC215364
0.8372	Intermediate Similarity	NPC78089
0.8353	Intermediate Similarity	NPC272814
0.8333	Intermediate Similarity	NPC281949
0.8333	Intermediate Similarity	NPC135776
0.8333	Intermediate Similarity	NPC10276
0.8333	Intermediate Similarity	NPC60386
0.8333	Intermediate Similarity	NPC473273
0.8333	Intermediate Similarity	NPC473234
0.8333	Intermediate Similarity	NPC25684
0.8333	Intermediate Similarity	NPC308656
0.8333	Intermediate Similarity	NPC473263
0.8333	Intermediate Similarity	NPC35089
0.8333	Intermediate Similarity	NPC301477
0.8315	Intermediate Similarity	NPC297474
0.8315	Intermediate Similarity	NPC54065
0.8315	Intermediate Similarity	NPC216284
0.8295	Intermediate Similarity	NPC217983
0.8295	Intermediate Similarity	NPC207114
0.8295	Intermediate Similarity	NPC178875
0.8293	Intermediate Similarity	NPC65603
0.8293	Intermediate Similarity	NPC53581
0.8293	Intermediate Similarity	NPC103987
0.8276	Intermediate Similarity	NPC284902
0.8276	Intermediate Similarity	NPC56593
0.8276	Intermediate Similarity	NPC50637
0.8272	Intermediate Similarity	NPC138408
0.8272	Intermediate Similarity	NPC193351
0.8272	Intermediate Similarity	NPC226669
0.8242	Intermediate Similarity	NPC262133
0.8242	Intermediate Similarity	NPC470010
0.8242	Intermediate Similarity	NPC323008
0.8242	Intermediate Similarity	NPC470013
0.8222	Intermediate Similarity	NPC171360
0.8222	Intermediate Similarity	NPC57304
0.8222	Intermediate Similarity	NPC286341
0.8222	Intermediate Similarity	NPC191339
0.8222	Intermediate Similarity	NPC35959
0.8222	Intermediate Similarity	NPC133888
0.8222	Intermediate Similarity	NPC29821
0.8222	Intermediate Similarity	NPC184063
0.8222	Intermediate Similarity	NPC63193
0.8222	Intermediate Similarity	NPC293001
0.8222	Intermediate Similarity	NPC155215
0.8202	Intermediate Similarity	NPC155935
0.8191	Intermediate Similarity	NPC70865
0.8182	Intermediate Similarity	NPC231889
0.8182	Intermediate Similarity	NPC160138
0.8172	Intermediate Similarity	NPC108475
0.8172	Intermediate Similarity	NPC170143
0.8172	Intermediate Similarity	NPC213947
0.8152	Intermediate Similarity	NPC163228
0.8152	Intermediate Similarity	NPC304886
0.8152	Intermediate Similarity	NPC476053
0.8152	Intermediate Similarity	NPC472873
0.8148	Intermediate Similarity	NPC469641
0.8148	Intermediate Similarity	NPC469643
0.814	Intermediate Similarity	NPC250315
0.814	Intermediate Similarity	NPC54468
0.814	Intermediate Similarity	NPC245665
0.8132	Intermediate Similarity	NPC153590
0.8132	Intermediate Similarity	NPC472874
0.8132	Intermediate Similarity	NPC258216
0.8118	Intermediate Similarity	NPC47635
0.8118	Intermediate Similarity	NPC141810
0.8118	Intermediate Similarity	NPC255580
0.8118	Intermediate Similarity	NPC39411
0.8111	Intermediate Similarity	NPC19087
0.8111	Intermediate Similarity	NPC35809
0.8111	Intermediate Similarity	NPC62815
0.8095	Intermediate Similarity	NPC470244
0.8095	Intermediate Similarity	NPC470239
0.8095	Intermediate Similarity	NPC617
0.809	Intermediate Similarity	NPC202672
0.8072	Intermediate Similarity	NPC195785
0.8072	Intermediate Similarity	NPC15975
0.8072	Intermediate Similarity	NPC208223
0.8068	Intermediate Similarity	NPC187661
0.8068	Intermediate Similarity	NPC261253
0.8068	Intermediate Similarity	NPC474045
0.8068	Intermediate Similarity	NPC469676
0.8065	Intermediate Similarity	NPC18019
0.8065	Intermediate Similarity	NPC24956
0.8046	Intermediate Similarity	NPC224386
0.8046	Intermediate Similarity	NPC194859
0.8022	Intermediate Similarity	NPC12172
0.8022	Intermediate Similarity	NPC208886
0.8022	Intermediate Similarity	NPC290651
0.8022	Intermediate Similarity	NPC221282
0.8022	Intermediate Similarity	NPC475925
0.8	Intermediate Similarity	NPC472955
0.8	Intermediate Similarity	NPC32922
0.8	Intermediate Similarity	NPC38392
0.8	Intermediate Similarity	NPC151770
0.8	Intermediate Similarity	NPC295312
0.8	Intermediate Similarity	NPC474981
0.8	Intermediate Similarity	NPC73052
0.8	Intermediate Similarity	NPC307411
0.8	Intermediate Similarity	NPC258965
0.8	Intermediate Similarity	NPC156658
0.8	Intermediate Similarity	NPC293418
0.8	Intermediate Similarity	NPC290508
0.8	Intermediate Similarity	NPC166919
0.8	Intermediate Similarity	NPC6823
0.7979	Intermediate Similarity	NPC471150
0.7978	Intermediate Similarity	NPC201658
0.7955	Intermediate Similarity	NPC474547
0.7952	Intermediate Similarity	NPC235906
0.7952	Intermediate Similarity	NPC123360
0.7938	Intermediate Similarity	NPC124881
0.7935	Intermediate Similarity	NPC475657
0.7935	Intermediate Similarity	NPC81419
0.7935	Intermediate Similarity	NPC200237
0.7935	Intermediate Similarity	NPC179746
0.7931	Intermediate Similarity	NPC170286
0.7931	Intermediate Similarity	NPC128429
0.7931	Intermediate Similarity	NPC215294
0.7931	Intermediate Similarity	NPC39588
0.7927	Intermediate Similarity	NPC476355
0.7927	Intermediate Similarity	NPC140287
0.7912	Intermediate Similarity	NPC329857
0.7912	Intermediate Similarity	NPC51004
0.7912	Intermediate Similarity	NPC312042
0.7912	Intermediate Similarity	NPC469718
0.7912	Intermediate Similarity	NPC475748
0.7901	Intermediate Similarity	NPC163003
0.7882	Intermediate Similarity	NPC63649
0.7882	Intermediate Similarity	NPC472965
0.7882	Intermediate Similarity	NPC264227
0.7875	Intermediate Similarity	NPC5714
0.7872	Intermediate Similarity	NPC91771
0.7872	Intermediate Similarity	NPC142529
0.7865	Intermediate Similarity	NPC162071
0.7865	Intermediate Similarity	NPC238593
0.7865	Intermediate Similarity	NPC470242
0.7857	Intermediate Similarity	NPC100487
0.7849	Intermediate Similarity	NPC473330
0.7849	Intermediate Similarity	NPC473316
0.7849	Intermediate Similarity	NPC476267
0.7849	Intermediate Similarity	NPC140543
0.7849	Intermediate Similarity	NPC474338
0.7841	Intermediate Similarity	NPC472957
0.7841	Intermediate Similarity	NPC472958
0.7835	Intermediate Similarity	NPC86077
0.7831	Intermediate Similarity	NPC155587
0.7826	Intermediate Similarity	NPC20713
0.7826	Intermediate Similarity	NPC184463
0.7826	Intermediate Similarity	NPC30515
0.7816	Intermediate Similarity	NPC173609
0.7816	Intermediate Similarity	NPC89555
0.7812	Intermediate Similarity	NPC186861
0.7802	Intermediate Similarity	NPC268298

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 NPC235792 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	217
0.1-0.2	2167
0.2-0.3	4077
0.3-0.4	1854
0.4-0.5	506
0.5-0.6	264
0.6-0.7	54
0.7-0.8	11
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8409	Intermediate Similarity	NPD1695	Approved
0.7753	Intermediate Similarity	NPD1733	Clinical (unspecified phase)
0.77	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7216	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7158	Intermediate Similarity	NPD5785	Approved
0.7143	Intermediate Similarity	NPD5362	Discontinued
0.7143	Intermediate Similarity	NPD6371	Approved
0.7111	Intermediate Similarity	NPD5369	Approved
0.7097	Intermediate Similarity	NPD4249	Approved
0.7087	Intermediate Similarity	NPD6008	Approved
0.7033	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD4251	Approved
0.7021	Intermediate Similarity	NPD4250	Approved
0.7009	Intermediate Similarity	NPD6053	Discontinued
0.6989	Remote Similarity	NPD1694	Approved
0.6989	Remote Similarity	NPD5363	Approved
0.6989	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6848	Remote Similarity	NPD4269	Approved
0.6848	Remote Similarity	NPD4270	Approved
0.6804	Remote Similarity	NPD46	Approved
0.6804	Remote Similarity	NPD6698	Approved
0.6771	Remote Similarity	NPD6903	Approved
0.6768	Remote Similarity	NPD5282	Discontinued
0.6737	Remote Similarity	NPD5330	Approved
0.6737	Remote Similarity	NPD6684	Approved
0.6737	Remote Similarity	NPD6409	Approved
0.6737	Remote Similarity	NPD5786	Approved
0.6737	Remote Similarity	NPD7334	Approved
0.6737	Remote Similarity	NPD7146	Approved
0.6737	Remote Similarity	NPD7521	Approved
0.6735	Remote Similarity	NPD5693	Phase 1
0.67	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6435	Approved
0.6667	Remote Similarity	NPD5209	Approved
0.6667	Remote Similarity	NPD7638	Approved
0.6633	Remote Similarity	NPD5207	Approved
0.663	Remote Similarity	NPD4820	Approved
0.663	Remote Similarity	NPD4819	Approved
0.663	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.663	Remote Similarity	NPD4822	Approved
0.663	Remote Similarity	NPD4252	Approved
0.663	Remote Similarity	NPD4821	Approved
0.6602	Remote Similarity	NPD7640	Approved
0.6602	Remote Similarity	NPD7639	Approved
0.6598	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6596	Remote Similarity	NPD7154	Phase 3
0.6596	Remote Similarity	NPD5332	Approved
0.6596	Remote Similarity	NPD5331	Approved
0.6559	Remote Similarity	NPD4790	Discontinued
0.6548	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.65	Remote Similarity	NPD6399	Phase 3
0.6465	Remote Similarity	NPD7838	Discovery
0.6452	Remote Similarity	NPD5368	Approved
0.6436	Remote Similarity	NPD6001	Approved
0.6429	Remote Similarity	NPD5737	Approved
0.6429	Remote Similarity	NPD6672	Approved
0.6413	Remote Similarity	NPD4271	Approved
0.6413	Remote Similarity	NPD4268	Approved
0.6413	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6373	Remote Similarity	NPD5695	Phase 3
0.6364	Remote Similarity	NPD6080	Approved
0.6364	Remote Similarity	NPD6051	Approved
0.6364	Remote Similarity	NPD6673	Approved
0.6364	Remote Similarity	NPD6904	Approved
0.6346	Remote Similarity	NPD4225	Approved
0.6346	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6346	Remote Similarity	NPD5696	Approved
0.6337	Remote Similarity	NPD5779	Approved
0.6337	Remote Similarity	NPD5778	Approved
0.633	Remote Similarity	NPD6686	Approved
0.6306	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.63	Remote Similarity	NPD5692	Phase 3
0.6264	Remote Similarity	NPD8039	Approved
0.6263	Remote Similarity	NPD5208	Approved
0.625	Remote Similarity	NPD6084	Phase 2
0.625	Remote Similarity	NPD6083	Phase 2
0.6239	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6238	Remote Similarity	NPD7983	Approved
0.6238	Remote Similarity	NPD6050	Approved
0.6238	Remote Similarity	NPD5694	Approved
0.6224	Remote Similarity	NPD6098	Approved
0.6174	Remote Similarity	NPD7115	Discovery
0.6168	Remote Similarity	NPD7632	Discontinued
0.6132	Remote Similarity	NPD6648	Approved
0.6111	Remote Similarity	NPD6052	Approved
0.6091	Remote Similarity	NPD5697	Approved
0.6078	Remote Similarity	NPD5284	Approved
0.6078	Remote Similarity	NPD5281	Approved
0.6078	Remote Similarity	NPD7637	Suspended
0.6075	Remote Similarity	NPD5344	Discontinued
0.6071	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6053	Remote Similarity	NPD4632	Approved
0.604	Remote Similarity	NPD6101	Approved
0.604	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6036	Remote Similarity	NPD6011	Approved
0.6036	Remote Similarity	NPD7320	Approved
0.6036	Remote Similarity	NPD6899	Approved
0.6036	Remote Similarity	NPD6881	Approved
0.6033	Remote Similarity	NPD7507	Approved
0.602	Remote Similarity	NPD3666	Approved
0.602	Remote Similarity	NPD3668	Phase 3
0.602	Remote Similarity	NPD3133	Approved
0.602	Remote Similarity	NPD3665	Phase 1
0.6018	Remote Similarity	NPD6650	Approved
0.6018	Remote Similarity	NPD6649	Approved
0.6	Remote Similarity	NPD6675	Approved
0.6	Remote Similarity	NPD5739	Approved
0.6	Remote Similarity	NPD7128	Approved
0.6	Remote Similarity	NPD6402	Approved
0.5982	Remote Similarity	NPD6014	Approved
0.5982	Remote Similarity	NPD6372	Approved
0.5982	Remote Similarity	NPD6012	Approved
0.5982	Remote Similarity	NPD6013	Approved
0.5982	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.5982	Remote Similarity	NPD6373	Approved
0.5979	Remote Similarity	NPD3667	Approved
0.5962	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.5962	Remote Similarity	NPD7900	Approved
0.595	Remote Similarity	NPD7492	Approved
0.5946	Remote Similarity	NPD5701	Approved
0.5946	Remote Similarity	NPD6412	Phase 2
0.5929	Remote Similarity	NPD7290	Approved
0.5929	Remote Similarity	NPD6883	Approved
0.5929	Remote Similarity	NPD7102	Approved
0.5922	Remote Similarity	NPD8035	Phase 2
0.5922	Remote Similarity	NPD6411	Approved
0.5922	Remote Similarity	NPD8034	Phase 2
0.5918	Remote Similarity	NPD6695	Phase 3
0.5905	Remote Similarity	NPD4629	Approved
0.5905	Remote Similarity	NPD5210	Approved
0.5905	Remote Similarity	NPD5654	Approved
0.5902	Remote Similarity	NPD6616	Approved
0.59	Remote Similarity	NPD3618	Phase 1
0.59	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.5897	Remote Similarity	NPD6009	Approved
0.5895	Remote Similarity	NPD4802	Phase 2
0.5895	Remote Similarity	NPD4238	Approved
0.5887	Remote Similarity	NPD7319	Approved
0.5882	Remote Similarity	NPD5370	Suspended
0.5882	Remote Similarity	NPD4753	Phase 2
0.5882	Remote Similarity	NPD6319	Approved
0.5882	Remote Similarity	NPD6054	Approved
0.5877	Remote Similarity	NPD6869	Approved
0.5877	Remote Similarity	NPD8130	Phase 1
0.5877	Remote Similarity	NPD6847	Approved
0.5877	Remote Similarity	NPD6617	Approved
0.5873	Remote Similarity	NPD6845	Suspended
0.5859	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.5859	Remote Similarity	NPD4786	Approved
0.5854	Remote Similarity	NPD7078	Approved
0.5849	Remote Similarity	NPD7839	Suspended
0.5842	Remote Similarity	NPD3573	Approved
0.5833	Remote Similarity	NPD5983	Phase 2
0.5833	Remote Similarity	NPD8513	Phase 3
0.5833	Remote Similarity	NPD8515	Approved
0.5833	Remote Similarity	NPD6015	Approved
0.5833	Remote Similarity	NPD8516	Approved
0.5833	Remote Similarity	NPD6016	Approved
0.5833	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.5833	Remote Similarity	NPD8517	Approved
0.5826	Remote Similarity	NPD6882	Approved
0.5826	Remote Similarity	NPD8297	Approved
0.5816	Remote Similarity	NPD4223	Phase 3
0.5816	Remote Similarity	NPD4221	Approved
0.581	Remote Similarity	NPD7748	Approved
0.5806	Remote Similarity	NPD7736	Approved
0.5804	Remote Similarity	NPD6614	Approved
0.5794	Remote Similarity	NPD5959	Approved
0.5794	Remote Similarity	NPD7260	Phase 2
0.5794	Remote Similarity	NPD7902	Approved
0.5785	Remote Similarity	NPD5988	Approved
0.5785	Remote Similarity	NPD6370	Approved
0.5769	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.5765	Remote Similarity	NPD3198	Approved
0.5758	Remote Similarity	NPD4788	Approved
0.575	Remote Similarity	NPD6059	Approved
0.5743	Remote Similarity	NPD5279	Phase 3
0.5743	Remote Similarity	NPD6422	Discontinued
0.5743	Remote Similarity	NPD5690	Phase 2
0.5739	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.5739	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.5738	Remote Similarity	NPD7604	Phase 2
0.5727	Remote Similarity	NPD5211	Phase 2
0.5726	Remote Similarity	NPD8293	Discontinued
0.5714	Remote Similarity	NPD7328	Approved
0.5714	Remote Similarity	NPD7327	Approved
0.5714	Remote Similarity	NPD4202	Approved
0.5702	Remote Similarity	NPD8033	Approved
0.5701	Remote Similarity	NPD5349	Clinical (unspecified phase)
0.57	Remote Similarity	NPD4197	Approved
0.5688	Remote Similarity	NPD5285	Approved
0.5688	Remote Similarity	NPD4696	Approved
0.5688	Remote Similarity	NPD5286	Approved
0.5686	Remote Similarity	NPD7524	Approved
0.5686	Remote Similarity	NPD7750	Discontinued
0.5678	Remote Similarity	NPD6274	Approved
0.5667	Remote Similarity	NPD7516	Approved
0.5664	Remote Similarity	NPD6685	Approved
0.5652	Remote Similarity	NPD6420	Discontinued
0.5648	Remote Similarity	NPD4755	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