NPASS Compound

Structure

NPC298190 OpenBabel07101718222D 23 26 0 0 1 0 0 0 0 0999 V2000 3.4641 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3914 -2.6088 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3273 -2.4449 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8228 -0.7753 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5176 -1.3259 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8569 -1.0341 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9716 -2.2169 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3735 -2.4701 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -3.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.5299 -1.4824 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4330 -0.7500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -2.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.4330 -0.7500 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.2645 -2.9240 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 1 13 1 0 0 0 0 4 5 1 0 0 0 0 4 13 1 0 0 0 0 5 16 1 0 0 0 0 6 8 1 0 0 0 0 6 14 1 0 0 0 0 7 9 2 0 0 0 0 7 14 1 0 0 0 0 8 19 1 0 0 0 0 9 22 1 0 0 0 0 10 17 1 0 0 0 0 11 15 1 0 0 0 0 11 20 1 0 0 0 0 12 14 2 0 0 0 0 12 22 1 0 0 0 0 13 19 1 6 0 0 0 15 10 1 1 0 0 0 15 23 1 0 0 0 0 16 17 2 0 0 0 0 16 20 1 0 0 0 0 17 19 1 0 0 0 0 18 20 1 0 0 0 0 18 21 2 0 0 0 0 18 23 1 0 0 0 0 19 2 1 6 0 0 0 20 3 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	314.19
Volume:	336.075
LogP:	4.642
LogD:	4.06
LogS:	-4.085
# Rotatable Bonds:	3
TPSA:	39.44
# H-Bond Aceptor:	3
# H-Bond Donor:	0
# Rings:	4
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.601
Synthetic Accessibility Score:	5.43
Fsp3:	0.65
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.687
MDCK Permeability:	3.2956530048977584e-05
Pgp-inhibitor:	0.059
Pgp-substrate:	0.006
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.007
30% Bioavailability (F30%):	0.03

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.05
Plasma Protein Binding (PPB):	94.81616973876953%
Volume Distribution (VD):	2.425
Pgp-substrate:	3.3952600955963135%

ADMET: Metabolism

CYP1A2-inhibitor:	0.168
CYP1A2-substrate:	0.155
CYP2C19-inhibitor:	0.808
CYP2C19-substrate:	0.817
CYP2C9-inhibitor:	0.561
CYP2C9-substrate:	0.079
CYP2D6-inhibitor:	0.711
CYP2D6-substrate:	0.073
CYP3A4-inhibitor:	0.917
CYP3A4-substrate:	0.548

ADMET: Excretion

Clearance (CL):	17.98
Half-life (T1/2):	0.051

ADMET: Toxicity

hERG Blockers:	0.012
Human Hepatotoxicity (H-HT):	0.508
Drug-inuced Liver Injury (DILI):	0.353
AMES Toxicity:	0.016
Rat Oral Acute Toxicity:	0.899
Maximum Recommended Daily Dose:	0.927
Skin Sensitization:	0.113
Carcinogencity:	0.936
Eye Corrosion:	0.236
Eye Irritation:	0.152
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: NPC298190

Natural Product ID:	NPC298190
*Common Name:**	FDUDLSYSEPOLKN-VGJAGTOYSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	FDUDLSYSEPOLKN-VGJAGTOYSA-N
Standard InCHI:	InChI=1S/C20H26O3/c1-13-4-5-16-17(10-15-11-20(16,3)18(21)23-15)19(13,2)8-6-14-7-9-22-12-14/h7,9,12-13,15H,4-6,8,10-11H2,1-3H3/t13-,15+,19+,20+/m1/s1
SMILES:	C[C@@H]1CCC2=C(C[C@H]3C[C@]2(C)C(=O)O3)[C@@]1(C)CCc1ccoc1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL481641
PubChem CID:	21574257
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones [CHEMONTID:0001538] Diterpene lactones

*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
NPO1396	Cladogynos orientalis	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[15679308]
NPO1396	Cladogynos orientalis	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	1
MIC	1

Activity Type	# Activity
Cell Line	1
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT639	Cell Line	NCI-H187	Homo sapiens	IC50	<	5.0	ug.mL-1	PMID[554501]
NPT88	Organism	Mycobacterium tuberculosis	Mycobacterium tuberculosis	MIC	<	12.5	ug.mL-1	PMID[554501]

☑ 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 NPC298190 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	277
0.1-0.2	1374
0.2-0.3	3142
0.3-0.4	7889
0.4-0.5	12477
0.5-0.6	12293
0.6-0.7	4516
0.7-0.8	580
0.8-0.85	107
0.85-0.9	26
0.9-0.95	11
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
0.9535	High Similarity	NPC470742
0.9462	High Similarity	NPC236532
0.938	High Similarity	NPC92941
0.9206	High Similarity	NPC83178
0.916	High Similarity	NPC146872
0.904	High Similarity	NPC16922
0.8984	High Similarity	NPC207294
0.8984	High Similarity	NPC112706
0.8955	High Similarity	NPC90953
0.8931	High Similarity	NPC471006
0.8931	High Similarity	NPC470740
0.8923	High Similarity	NPC61788
0.8906	High Similarity	NPC319140
0.8906	High Similarity	NPC95567
0.8898	High Similarity	NPC179354
0.8889	High Similarity	NPC56197
0.8881	High Similarity	NPC220094
0.8832	High Similarity	NPC470741
0.8832	High Similarity	NPC223415
0.8828	High Similarity	NPC138139
0.8828	High Similarity	NPC46536
0.8828	High Similarity	NPC74612
0.8819	High Similarity	NPC65735
0.8819	High Similarity	NPC188377
0.8806	High Similarity	NPC310830
0.8788	High Similarity	NPC218838
0.8768	High Similarity	NPC199044
0.8768	High Similarity	NPC238843
0.8768	High Similarity	NPC251865
0.8692	High Similarity	NPC477039
0.8686	High Similarity	NPC20500
0.8682	High Similarity	NPC23086
0.8667	High Similarity	NPC307401
0.8643	High Similarity	NPC471292
0.8643	High Similarity	NPC346
0.864	High Similarity	NPC243704
0.8626	High Similarity	NPC198904
0.8626	High Similarity	NPC59502
0.8603	High Similarity	NPC476943
0.8592	High Similarity	NPC471001
0.8582	High Similarity	NPC221809
0.8571	High Similarity	NPC471817
0.8571	High Similarity	NPC56731
0.8561	High Similarity	NPC21460
0.8561	High Similarity	NPC267632
0.855	High Similarity	NPC477123
0.855	High Similarity	NPC477966
0.8548	High Similarity	NPC150895
0.854	High Similarity	NPC202260
0.8531	High Similarity	NPC5180
0.8519	High Similarity	NPC476947
0.8516	High Similarity	NPC317217
0.8516	High Similarity	NPC477967
0.8516	High Similarity	NPC36255
0.85	High Similarity	NPC476944
0.8496	Intermediate Similarity	NPC89133
0.8489	Intermediate Similarity	NPC121158
0.8485	Intermediate Similarity	NPC208389
0.8472	Intermediate Similarity	NPC291150
0.8472	Intermediate Similarity	NPC116717
0.8462	Intermediate Similarity	NPC234494
0.8462	Intermediate Similarity	NPC195325
0.8451	Intermediate Similarity	NPC10088
0.8451	Intermediate Similarity	NPC250228
0.8451	Intermediate Similarity	NPC471174
0.8414	Intermediate Similarity	NPC471002
0.8409	Intermediate Similarity	NPC476917
0.8409	Intermediate Similarity	NPC327527
0.8409	Intermediate Similarity	NPC477040
0.8403	Intermediate Similarity	NPC470997
0.8394	Intermediate Similarity	NPC42400
0.8392	Intermediate Similarity	NPC476941
0.8392	Intermediate Similarity	NPC476942
0.8392	Intermediate Similarity	NPC93666
0.8385	Intermediate Similarity	NPC243269
0.8385	Intermediate Similarity	NPC83115
0.8385	Intermediate Similarity	NPC477038
0.8385	Intermediate Similarity	NPC130275
0.8385	Intermediate Similarity	NPC477965
0.8382	Intermediate Similarity	NPC158525
0.838	Intermediate Similarity	NPC470999
0.838	Intermediate Similarity	NPC262198
0.837	Intermediate Similarity	NPC293253
0.8369	Intermediate Similarity	NPC142113
0.8357	Intermediate Similarity	NPC473152
0.8356	Intermediate Similarity	NPC57998
0.8345	Intermediate Similarity	NPC18135
0.8345	Intermediate Similarity	NPC272590
0.8333	Intermediate Similarity	NPC472654
0.8322	Intermediate Similarity	NPC216755
0.8322	Intermediate Similarity	NPC476937
0.8322	Intermediate Similarity	NPC476938
0.8321	Intermediate Similarity	NPC471074
0.8321	Intermediate Similarity	NPC230979
0.8321	Intermediate Similarity	NPC214572
0.8321	Intermediate Similarity	NPC473885
0.831	Intermediate Similarity	NPC185456
0.8299	Intermediate Similarity	NPC214541
0.8299	Intermediate Similarity	NPC44675
0.8299	Intermediate Similarity	NPC296807
0.8299	Intermediate Similarity	NPC155939
0.8299	Intermediate Similarity	NPC141538
0.8298	Intermediate Similarity	NPC80635
0.8288	Intermediate Similarity	NPC246164
0.8288	Intermediate Similarity	NPC476939
0.8288	Intermediate Similarity	NPC33938
0.8288	Intermediate Similarity	NPC476940
0.8288	Intermediate Similarity	NPC268905
0.8284	Intermediate Similarity	NPC476925
0.8281	Intermediate Similarity	NPC473969
0.8276	Intermediate Similarity	NPC159927
0.8276	Intermediate Similarity	NPC469335
0.8276	Intermediate Similarity	NPC476936
0.8276	Intermediate Similarity	NPC156189
0.8273	Intermediate Similarity	NPC474722
0.8268	Intermediate Similarity	NPC208906
0.8268	Intermediate Similarity	NPC212918
0.8268	Intermediate Similarity	NPC144745
0.8261	Intermediate Similarity	NPC310043
0.8261	Intermediate Similarity	NPC186626
0.8254	Intermediate Similarity	NPC28054
0.8252	Intermediate Similarity	NPC276676
0.8239	Intermediate Similarity	NPC84479
0.8227	Intermediate Similarity	NPC52412
0.8226	Intermediate Similarity	NPC105249
0.8219	Intermediate Similarity	NPC471000
0.8214	Intermediate Similarity	NPC148374
0.8214	Intermediate Similarity	NPC67003
0.8207	Intermediate Similarity	NPC470791
0.8207	Intermediate Similarity	NPC470790
0.8203	Intermediate Similarity	NPC87466
0.8195	Intermediate Similarity	NPC246392
0.8195	Intermediate Similarity	NPC290955
0.8195	Intermediate Similarity	NPC137570
0.8195	Intermediate Similarity	NPC476016
0.8194	Intermediate Similarity	NPC71821
0.8194	Intermediate Similarity	NPC302987
0.8194	Intermediate Similarity	NPC255414
0.8194	Intermediate Similarity	NPC470941
0.8188	Intermediate Similarity	NPC261597
0.8188	Intermediate Similarity	NPC197137
0.8188	Intermediate Similarity	NPC46896
0.8188	Intermediate Similarity	NPC470118
0.8182	Intermediate Similarity	NPC34056
0.8176	Intermediate Similarity	NPC25351
0.8176	Intermediate Similarity	NPC92979
0.8169	Intermediate Similarity	NPC243577
0.8169	Intermediate Similarity	NPC476946
0.8163	Intermediate Similarity	NPC182427
0.8163	Intermediate Similarity	NPC29695
0.8163	Intermediate Similarity	NPC469503
0.8163	Intermediate Similarity	NPC308205
0.8163	Intermediate Similarity	NPC322546
0.8163	Intermediate Similarity	NPC75906
0.8156	Intermediate Similarity	NPC205765
0.8154	Intermediate Similarity	NPC97566
0.8151	Intermediate Similarity	NPC196864
0.8151	Intermediate Similarity	NPC196846
0.8151	Intermediate Similarity	NPC476122
0.8151	Intermediate Similarity	NPC477404
0.8134	Intermediate Similarity	NPC279877
0.8134	Intermediate Similarity	NPC26532
0.8133	Intermediate Similarity	NPC474932
0.8125	Intermediate Similarity	NPC233763
0.8125	Intermediate Similarity	NPC131801
0.8121	Intermediate Similarity	NPC104736
0.812	Intermediate Similarity	NPC329922
0.812	Intermediate Similarity	NPC81912
0.812	Intermediate Similarity	NPC329694
0.812	Intermediate Similarity	NPC474260
0.8108	Intermediate Similarity	NPC471863
0.8108	Intermediate Similarity	NPC34421
0.8108	Intermediate Similarity	NPC178932
0.8108	Intermediate Similarity	NPC30222
0.8108	Intermediate Similarity	NPC237259
0.8108	Intermediate Similarity	NPC98206
0.8106	Intermediate Similarity	NPC178382
0.8085	Intermediate Similarity	NPC90296
0.8082	Intermediate Similarity	NPC95526
0.8082	Intermediate Similarity	NPC125182
0.8082	Intermediate Similarity	NPC69647
0.8082	Intermediate Similarity	NPC470998
0.8074	Intermediate Similarity	NPC120836
0.8074	Intermediate Similarity	NPC223063
0.8069	Intermediate Similarity	NPC224418
0.8067	Intermediate Similarity	NPC472776
0.8067	Intermediate Similarity	NPC304692
0.8067	Intermediate Similarity	NPC472777
0.8067	Intermediate Similarity	NPC36655
0.8067	Intermediate Similarity	NPC472778
0.8067	Intermediate Similarity	NPC469847
0.8067	Intermediate Similarity	NPC299038
0.8067	Intermediate Similarity	NPC187149
0.8056	Intermediate Similarity	NPC290038
0.8054	Intermediate Similarity	NPC35000
0.8054	Intermediate Similarity	NPC469336
0.8054	Intermediate Similarity	NPC469850
0.8045	Intermediate Similarity	NPC75557
0.8045	Intermediate Similarity	NPC71274
0.8045	Intermediate Similarity	NPC300098

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 NPC298190 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	249
0.1-0.2	1009
0.2-0.3	1908
0.3-0.4	2694
0.4-0.5	2137
0.5-0.6	950
0.6-0.7	193
0.7-0.8	10
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
0.7697	Intermediate Similarity	NPD5760	Phase 2
0.7697	Intermediate Similarity	NPD5761	Phase 2
0.7639	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7584	Intermediate Similarity	NPD6273	Approved
0.75	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD8032	Phase 2
0.7248	Intermediate Similarity	NPD4628	Phase 3
0.7212	Intermediate Similarity	NPD6764	Approved
0.7212	Intermediate Similarity	NPD6765	Approved
0.7176	Intermediate Similarity	NPD2181	Clinical (unspecified phase)
0.7162	Intermediate Similarity	NPD1471	Phase 3
0.7143	Intermediate Similarity	NPD1241	Discontinued
0.7143	Intermediate Similarity	NPD2799	Discontinued
0.7122	Intermediate Similarity	NPD3972	Approved
0.7101	Intermediate Similarity	NPD8434	Phase 2
0.708	Intermediate Similarity	NPD5585	Approved
0.705	Intermediate Similarity	NPD1281	Approved
0.7041	Intermediate Similarity	NPD6785	Approved
0.7041	Intermediate Similarity	NPD6784	Approved
0.7029	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD1876	Approved
0.702	Intermediate Similarity	NPD7003	Approved
0.6986	Remote Similarity	NPD4140	Approved
0.6986	Remote Similarity	NPD2979	Phase 3
0.6981	Remote Similarity	NPD5616	Clinical (unspecified phase)
0.6968	Remote Similarity	NPD920	Approved
0.6957	Remote Similarity	NPD5691	Approved
0.6948	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD6832	Phase 2
0.6933	Remote Similarity	NPD2346	Discontinued
0.6928	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6908	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6908	Remote Similarity	NPD4110	Phase 3
0.6906	Remote Similarity	NPD17	Approved
0.6901	Remote Similarity	NPD1283	Approved
0.6879	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD2438	Suspended
0.6831	Remote Similarity	NPD4359	Approved
0.6831	Remote Similarity	NPD5327	Phase 3
0.6824	Remote Similarity	NPD6355	Discontinued
0.6821	Remote Similarity	NPD2344	Approved
0.6809	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.68	Remote Similarity	NPD3748	Approved
0.6797	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6761	Remote Similarity	NPD1608	Approved
0.6757	Remote Similarity	NPD4307	Phase 2
0.6755	Remote Similarity	NPD2531	Phase 2
0.6742	Remote Similarity	NPD3134	Approved
0.6736	Remote Similarity	NPD2797	Approved
0.6736	Remote Similarity	NPD1049	Clinical (unspecified phase)
0.6735	Remote Similarity	NPD2313	Discontinued
0.6732	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6732	Remote Similarity	NPD1243	Approved
0.6714	Remote Similarity	NPD1651	Approved
0.6711	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.669	Remote Similarity	NPD2798	Approved
0.6689	Remote Similarity	NPD4870	Approved
0.6689	Remote Similarity	NPD6663	Approved
0.6667	Remote Similarity	NPD7458	Discontinued
0.6667	Remote Similarity	NPD1778	Approved
0.6667	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4626	Approved
0.6667	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD8127	Discontinued
0.6646	Remote Similarity	NPD919	Approved
0.6645	Remote Similarity	NPD2796	Approved
0.6645	Remote Similarity	NPD2309	Approved
0.6645	Remote Similarity	NPD4476	Approved
0.6645	Remote Similarity	NPD2935	Discontinued
0.6645	Remote Similarity	NPD3887	Approved
0.6645	Remote Similarity	NPD4477	Approved
0.6642	Remote Similarity	NPD2182	Approved
0.6627	Remote Similarity	NPD6808	Phase 2
0.6625	Remote Similarity	NPD7028	Phase 2
0.6625	Remote Similarity	NPD6599	Discontinued
0.6624	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6622	Remote Similarity	NPD3764	Approved
0.6621	Remote Similarity	NPD3266	Approved
0.6621	Remote Similarity	NPD3267	Approved
0.662	Remote Similarity	NPD7457	Clinical (unspecified phase)
0.6605	Remote Similarity	NPD7819	Suspended
0.6601	Remote Similarity	NPD6005	Phase 3
0.6601	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6601	Remote Similarity	NPD6004	Phase 3
0.6601	Remote Similarity	NPD6002	Phase 3
0.6601	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.66	Remote Similarity	NPD4618	Approved
0.66	Remote Similarity	NPD4622	Approved
0.6581	Remote Similarity	NPD8166	Discontinued
0.6581	Remote Similarity	NPD3750	Approved
0.6579	Remote Similarity	NPD4308	Phase 3
0.6575	Remote Similarity	NPD1019	Discontinued
0.6562	Remote Similarity	NPD3226	Approved
0.6558	Remote Similarity	NPD4534	Discontinued
0.6543	Remote Similarity	NPD6280	Approved
0.6543	Remote Similarity	NPD6279	Approved
0.6536	Remote Similarity	NPD1551	Phase 2
0.6533	Remote Similarity	NPD3140	Approved
0.6533	Remote Similarity	NPD3142	Approved
0.6531	Remote Similarity	NPD5736	Approved
0.6528	Remote Similarity	NPD9717	Approved
0.6525	Remote Similarity	NPD1894	Discontinued
0.6519	Remote Similarity	NPD2533	Approved
0.6519	Remote Similarity	NPD2534	Approved
0.6519	Remote Similarity	NPD2532	Approved
0.6513	Remote Similarity	NPD5689	Approved
0.6513	Remote Similarity	NPD5688	Approved
0.6512	Remote Similarity	NPD6559	Discontinued
0.651	Remote Similarity	NPD6798	Discontinued
0.651	Remote Similarity	NPD3268	Approved
0.6506	Remote Similarity	NPD5494	Approved
0.6503	Remote Similarity	NPD3496	Discontinued
0.6497	Remote Similarity	NPD7236	Approved
0.6496	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.649	Remote Similarity	NPD5735	Approved
0.6484	Remote Similarity	NPD4107	Approved
0.6481	Remote Similarity	NPD6873	Phase 2
0.6463	Remote Similarity	NPD5647	Approved
0.6452	Remote Similarity	NPD5958	Discontinued
0.6452	Remote Similarity	NPD2897	Discontinued
0.6449	Remote Similarity	NPD5535	Approved
0.6448	Remote Similarity	NPD4482	Phase 3
0.6447	Remote Similarity	NPD6353	Approved
0.6444	Remote Similarity	NPD1358	Approved
0.6443	Remote Similarity	NPD7008	Discontinued
0.6443	Remote Similarity	NPD7095	Approved
0.6438	Remote Similarity	NPD3873	Phase 3
0.6438	Remote Similarity	NPD3869	Phase 3
0.6424	Remote Similarity	NPD4966	Approved
0.6424	Remote Similarity	NPD4965	Approved
0.6424	Remote Similarity	NPD4967	Phase 2
0.6424	Remote Similarity	NPD4060	Phase 1
0.6424	Remote Similarity	NPD4947	Clinical (unspecified phase)
0.6419	Remote Similarity	NPD9494	Approved
0.6408	Remote Similarity	NPD9545	Approved
0.6402	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.64	Remote Similarity	NPD411	Approved
0.6395	Remote Similarity	NPD1203	Approved
0.6387	Remote Similarity	NPD2355	Clinical (unspecified phase)
0.6387	Remote Similarity	NPD5763	Approved
0.6387	Remote Similarity	NPD5762	Approved
0.6387	Remote Similarity	NPD2353	Approved
0.6386	Remote Similarity	NPD3749	Approved
0.6382	Remote Similarity	NPD1933	Approved
0.6382	Remote Similarity	NPD447	Suspended
0.6376	Remote Similarity	NPD2614	Approved
0.6369	Remote Similarity	NPD1247	Approved
0.6358	Remote Similarity	NPD2651	Approved
0.6358	Remote Similarity	NPD2649	Approved
0.6358	Remote Similarity	NPD4062	Phase 3
0.6358	Remote Similarity	NPD6233	Phase 2
0.6352	Remote Similarity	NPD6799	Approved
0.6352	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6351	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6347	Remote Similarity	NPD6234	Discontinued
0.6346	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6345	Remote Similarity	NPD1611	Approved
0.6345	Remote Similarity	NPD6287	Discontinued
0.6343	Remote Similarity	NPD164	Approved
0.634	Remote Similarity	NPD6653	Approved
0.6337	Remote Similarity	NPD5844	Phase 1
0.6335	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6325	Remote Similarity	NPD7768	Phase 2
0.6319	Remote Similarity	NPD2932	Approved
0.6312	Remote Similarity	NPD7157	Approved
0.6306	Remote Similarity	NPD2800	Approved
0.6299	Remote Similarity	NPD7097	Phase 1
0.6296	Remote Similarity	NPD9697	Approved
0.6296	Remote Similarity	NPD7239	Suspended
0.6291	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6291	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6289	Remote Similarity	NPD7440	Discontinued
0.6288	Remote Similarity	NPD1238	Approved
0.6287	Remote Similarity	NPD7075	Discontinued
0.6284	Remote Similarity	NPD6362	Approved
0.628	Remote Similarity	NPD6677	Suspended
0.628	Remote Similarity	NPD7411	Suspended
0.6277	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.625	Remote Similarity	NPD3025	Approved
0.625	Remote Similarity	NPD3024	Approved
0.6242	Remote Similarity	NPD6801	Discontinued
0.6242	Remote Similarity	NPD37	Approved
0.6241	Remote Similarity	NPD2629	Approved
0.6241	Remote Similarity	NPD5951	Approved
0.6235	Remote Similarity	NPD7427	Discontinued
0.6232	Remote Similarity	NPD2067	Discontinued
0.6228	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6226	Remote Similarity	NPD2354	Approved
0.6218	Remote Similarity	NPD6100	Approved
0.6218	Remote Similarity	NPD6099	Approved
0.6216	Remote Similarity	NPD8651	Approved
0.6214	Remote Similarity	NPD7094	Approved
0.6214	Remote Similarity	NPD6858	Approved
0.6207	Remote Similarity	NPD3019	Approved
0.6201	Remote Similarity	NPD7693	Approved
0.62	Remote Similarity	NPD2237	Approved
0.6199	Remote Similarity	NPD3926	Phase 2
0.619	Remote Similarity	NPD1481	Phase 2
0.6185	Remote Similarity	NPD7177	Discontinued
0.6182	Remote Similarity	NPD6386	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