NPASS Compound

Structure

NPC475053 OpenBabel07101718192D 25 27 0 0 1 0 0 0 0 0999 V2000 3.2165 2.7946 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8238 -3.1185 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3416 -2.2834 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1081 -1.7093 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0244 -1.6720 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1893 -1.1899 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7344 -0.4821 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0244 -2.6363 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7847 -0.6496 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7847 2.1270 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1893 1.7030 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7344 1.9595 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3542 0.2565 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.1893 -0.2256 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3542 1.2208 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.9496 1.6448 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.6198 0.7387 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 5.0244 0.2565 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8595 -3.1185 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9496 -0.1674 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 0.2110 2.2646 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.8595 -0.2256 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.8595 -4.0827 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.0244 1.2208 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 12 2 0 0 0 0 2 19 1 0 0 0 0 3 19 1 0 0 0 0 4 20 1 0 0 0 0 5 6 1 0 0 0 0 5 8 2 0 0 0 0 6 14 2 0 0 0 0 7 9 1 0 0 0 0 8 19 1 0 0 0 0 9 20 1 0 0 0 0 10 12 1 0 0 0 0 10 16 1 0 0 0 0 11 24 1 0 0 0 0 12 15 1 0 0 0 0 13 7 1 1 0 0 0 13 14 1 0 0 0 0 13 15 1 0 0 0 0 14 18 1 0 0 0 0 15 11 1 6 0 0 0 16 17 1 0 0 0 0 16 21 1 6 0 0 0 17 20 1 0 0 0 0 17 25 1 0 0 0 0 18 22 2 0 0 0 0 18 24 1 0 0 0 0 19 23 1 0 0 0 0 20 25 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	348.19
Volume:	362.212
LogP:	2.308
LogD:	1.93
LogS:	-3.386
# Rotatable Bonds:	2
TPSA:	79.29
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.346
Synthetic Accessibility Score:	5.353
Fsp3:	0.65
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:	-4.553
MDCK Permeability:	1.863889156084042e-05
Pgp-inhibitor:	0.002
Pgp-substrate:	0.012
Human Intestinal Absorption (HIA):	0.008
20% Bioavailability (F20%):	0.005
30% Bioavailability (F30%):	0.076

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.416
Plasma Protein Binding (PPB):	65.22269439697266%
Volume Distribution (VD):	0.518
Pgp-substrate:	27.476600646972656%

ADMET: Metabolism

CYP1A2-inhibitor:	0.052
CYP1A2-substrate:	0.262
CYP2C19-inhibitor:	0.049
CYP2C19-substrate:	0.734
CYP2C9-inhibitor:	0.042
CYP2C9-substrate:	0.081
CYP2D6-inhibitor:	0.021
CYP2D6-substrate:	0.226
CYP3A4-inhibitor:	0.27
CYP3A4-substrate:	0.326

ADMET: Excretion

Clearance (CL):	9.993
Half-life (T1/2):	0.21

ADMET: Toxicity

hERG Blockers:	0.141
Human Hepatotoxicity (H-HT):	0.911
Drug-inuced Liver Injury (DILI):	0.527
AMES Toxicity:	0.234
Rat Oral Acute Toxicity:	0.68
Maximum Recommended Daily Dose:	0.909
Skin Sensitization:	0.317
Carcinogencity:	0.917
Eye Corrosion:	0.003
Eye Irritation:	0.017
Respiratory Toxicity:	0.941

Download Data

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

Natural Product: NPC475053

Natural Product ID:	NPC475053
*Common Name:**	DHTWVKTXQLZELP-VOIRMJBLSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	DHTWVKTXQLZELP-VOIRMJBLSA-N
Standard InCHI:	InChI=1S/C20H28O5/c1-12-10-16(21)17-20(4,25-17)9-7-13-14(6-5-8-19(2,3)23)18(22)24-11-15(12)13/h5-6,8,13,15-17,21,23H,1,7,9-11H2,2-4H3/b8-5+,14-6-/t13-,15+,16-,17?,20?/m1/s1
SMILES:	CC12CCC3C(COC(=O)C3=CC=CC(C)(C)O)C(=C)CC(C1O2)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL494605
PubChem CID:	23252117
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000050] Lactones [CHEMONTID:0001244] Delta valerolactones

*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
NPO33424	xenia sp.	Species	Xeniidae	Eukaryota	n.a.	Indonesian	n.a.	PMID[12027764]

☑ 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
NPT168	Cell Line	P388	Mus musculus	IC50	>	1.0	ug.mL-1	PMID[460893]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	1.0	ug.mL-1	PMID[460893]
NPT139	Cell Line	HT-29	Homo sapiens	IC50	>	1.0	ug.mL-1	PMID[460893]
NPT170	Cell Line	SK-MEL-28	Homo sapiens	IC50	>	1.0	ug.mL-1	PMID[460893]

☑ 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 NPC475053 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	214
0.1-0.2	1126
0.2-0.3	3771
0.3-0.4	7006
0.4-0.5	15851
0.5-0.6	9237
0.6-0.7	4582
0.7-0.8	882
0.8-0.85	19
0.85-0.9	5
0.9-0.95	3
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9565	High Similarity	NPC272050
0.914	High Similarity	NPC476049
0.9022	High Similarity	NPC106040
0.9022	High Similarity	NPC115179
0.9022	High Similarity	NPC212598
0.8947	High Similarity	NPC107476
0.8696	High Similarity	NPC116575
0.8602	High Similarity	NPC474765
0.8557	High Similarity	NPC270013
0.8557	High Similarity	NPC14961
0.8495	Intermediate Similarity	NPC122502
0.8454	Intermediate Similarity	NPC474035
0.8454	Intermediate Similarity	NPC81386
0.8416	Intermediate Similarity	NPC473596
0.8387	Intermediate Similarity	NPC474369
0.8384	Intermediate Similarity	NPC40812
0.837	Intermediate Similarity	NPC53867
0.8351	Intermediate Similarity	NPC212486
0.8351	Intermediate Similarity	NPC475912
0.8333	Intermediate Similarity	NPC474761
0.8333	Intermediate Similarity	NPC476004
0.8333	Intermediate Similarity	NPC473448
0.8316	Intermediate Similarity	NPC153805
0.8316	Intermediate Similarity	NPC281516
0.83	Intermediate Similarity	NPC187761
0.83	Intermediate Similarity	NPC83895
0.8298	Intermediate Similarity	NPC164393
0.8298	Intermediate Similarity	NPC234038
0.8283	Intermediate Similarity	NPC476315
0.8283	Intermediate Similarity	NPC279621
0.828	Intermediate Similarity	NPC70424
0.828	Intermediate Similarity	NPC243618
0.828	Intermediate Similarity	NPC196487
0.828	Intermediate Similarity	NPC14575
0.828	Intermediate Similarity	NPC72464
0.8218	Intermediate Similarity	NPC288876
0.8191	Intermediate Similarity	NPC137033
0.8182	Intermediate Similarity	NPC36954
0.8173	Intermediate Similarity	NPC243998
0.8163	Intermediate Similarity	NPC475838
0.8163	Intermediate Similarity	NPC228451
0.8163	Intermediate Similarity	NPC125674
0.8144	Intermediate Similarity	NPC3952
0.8125	Intermediate Similarity	NPC474471
0.8125	Intermediate Similarity	NPC227379
0.8119	Intermediate Similarity	NPC187268
0.8119	Intermediate Similarity	NPC308567
0.8119	Intermediate Similarity	NPC473326
0.8119	Intermediate Similarity	NPC161855
0.8119	Intermediate Similarity	NPC222303
0.8119	Intermediate Similarity	NPC474213
0.8119	Intermediate Similarity	NPC475653
0.8119	Intermediate Similarity	NPC255592
0.8119	Intermediate Similarity	NPC261377
0.8105	Intermediate Similarity	NPC61527
0.81	Intermediate Similarity	NPC473291
0.8085	Intermediate Similarity	NPC9868
0.8085	Intermediate Similarity	NPC474776
0.8081	Intermediate Similarity	NPC71589
0.8081	Intermediate Similarity	NPC57405
0.8081	Intermediate Similarity	NPC474247
0.8081	Intermediate Similarity	NPC303942
0.8077	Intermediate Similarity	NPC474741
0.8073	Intermediate Similarity	NPC305044
0.8073	Intermediate Similarity	NPC265290
0.8061	Intermediate Similarity	NPC184463
0.8061	Intermediate Similarity	NPC30515
0.8021	Intermediate Similarity	NPC248602
0.802	Intermediate Similarity	NPC120299
0.8	Intermediate Similarity	NPC471494
0.8	Intermediate Similarity	NPC223450
0.8	Intermediate Similarity	NPC474547
0.8	Intermediate Similarity	NPC304886
0.7982	Intermediate Similarity	NPC101965
0.7982	Intermediate Similarity	NPC469463
0.7982	Intermediate Similarity	NPC469454
0.7982	Intermediate Similarity	NPC101400
0.7982	Intermediate Similarity	NPC469496
0.7981	Intermediate Similarity	NPC475945
0.7981	Intermediate Similarity	NPC475871
0.798	Intermediate Similarity	NPC81419
0.798	Intermediate Similarity	NPC179746
0.798	Intermediate Similarity	NPC476300
0.7979	Intermediate Similarity	NPC11620
0.7979	Intermediate Similarity	NPC170377
0.7963	Intermediate Similarity	NPC304180
0.7963	Intermediate Similarity	NPC179798
0.7961	Intermediate Similarity	NPC474742
0.7961	Intermediate Similarity	NPC476270
0.7959	Intermediate Similarity	NPC51004
0.7959	Intermediate Similarity	NPC475855
0.7959	Intermediate Similarity	NPC313670
0.7938	Intermediate Similarity	NPC202672
0.7925	Intermediate Similarity	NPC266514
0.7921	Intermediate Similarity	NPC255410
0.7921	Intermediate Similarity	NPC230800
0.7921	Intermediate Similarity	NPC473859
0.7917	Intermediate Similarity	NPC311163
0.7895	Intermediate Similarity	NPC186155
0.7895	Intermediate Similarity	NPC160517
0.7895	Intermediate Similarity	NPC78673
0.789	Intermediate Similarity	NPC98038
0.789	Intermediate Similarity	NPC313921
0.7885	Intermediate Similarity	NPC86077
0.7885	Intermediate Similarity	NPC474747
0.7879	Intermediate Similarity	NPC473321
0.7879	Intermediate Similarity	NPC470379
0.7879	Intermediate Similarity	NPC12172
0.7879	Intermediate Similarity	NPC470373
0.7879	Intermediate Similarity	NPC208886
0.7872	Intermediate Similarity	NPC474291
0.7872	Intermediate Similarity	NPC475936
0.787	Intermediate Similarity	NPC5103
0.787	Intermediate Similarity	NPC41551
0.7857	Intermediate Similarity	NPC474032
0.7857	Intermediate Similarity	NPC473564
0.7857	Intermediate Similarity	NPC307411
0.7857	Intermediate Similarity	NPC295312
0.7857	Intermediate Similarity	NPC83423
0.7849	Intermediate Similarity	NPC233377
0.7849	Intermediate Similarity	NPC474510
0.7843	Intermediate Similarity	NPC205143
0.7835	Intermediate Similarity	NPC231889
0.7835	Intermediate Similarity	NPC86005
0.7835	Intermediate Similarity	NPC160138
0.783	Intermediate Similarity	NPC472749
0.783	Intermediate Similarity	NPC472751
0.7822	Intermediate Similarity	NPC475659
0.7822	Intermediate Similarity	NPC300710
0.7822	Intermediate Similarity	NPC471141
0.7818	Intermediate Similarity	NPC56448
0.7818	Intermediate Similarity	NPC106395
0.7818	Intermediate Similarity	NPC46269
0.7812	Intermediate Similarity	NPC99395
0.7812	Intermediate Similarity	NPC21469
0.7812	Intermediate Similarity	NPC197903
0.781	Intermediate Similarity	NPC472750
0.781	Intermediate Similarity	NPC472747
0.781	Intermediate Similarity	NPC473624
0.78	Intermediate Similarity	NPC288240
0.78	Intermediate Similarity	NPC273579
0.78	Intermediate Similarity	NPC295204
0.78	Intermediate Similarity	NPC162205
0.7789	Intermediate Similarity	NPC250315
0.7789	Intermediate Similarity	NPC231601
0.7789	Intermediate Similarity	NPC475842
0.7789	Intermediate Similarity	NPC44261
0.7788	Intermediate Similarity	NPC116139
0.7788	Intermediate Similarity	NPC150923
0.7788	Intermediate Similarity	NPC164598
0.7788	Intermediate Similarity	NPC473332
0.7788	Intermediate Similarity	NPC474339
0.7778	Intermediate Similarity	NPC144133
0.7778	Intermediate Similarity	NPC38154
0.7778	Intermediate Similarity	NPC475748
0.7778	Intermediate Similarity	NPC473619
0.7778	Intermediate Similarity	NPC179394
0.7767	Intermediate Similarity	NPC203627
0.7766	Intermediate Similarity	NPC325031
0.7766	Intermediate Similarity	NPC474894
0.7757	Intermediate Similarity	NPC472263
0.7757	Intermediate Similarity	NPC469959
0.7757	Intermediate Similarity	NPC469957
0.7757	Intermediate Similarity	NPC477513
0.7757	Intermediate Similarity	NPC108682
0.7748	Intermediate Similarity	NPC133677
0.7748	Intermediate Similarity	NPC138303
0.7748	Intermediate Similarity	NPC67290
0.7745	Intermediate Similarity	NPC57664
0.7742	Intermediate Similarity	NPC469617
0.7742	Intermediate Similarity	NPC471537
0.7736	Intermediate Similarity	NPC203659
0.7736	Intermediate Similarity	NPC309190
0.7736	Intermediate Similarity	NPC472748
0.7736	Intermediate Similarity	NPC100487
0.7727	Intermediate Similarity	NPC123855
0.7727	Intermediate Similarity	NPC138757
0.7727	Intermediate Similarity	NPC66108
0.7727	Intermediate Similarity	NPC76550
0.7723	Intermediate Similarity	NPC474338
0.7723	Intermediate Similarity	NPC473316
0.7723	Intermediate Similarity	NPC473330
0.7723	Intermediate Similarity	NPC469491
0.7719	Intermediate Similarity	NPC475885
0.7714	Intermediate Similarity	NPC149371
0.7714	Intermediate Similarity	NPC66110
0.7714	Intermediate Similarity	NPC197835
0.7714	Intermediate Similarity	NPC140591
0.7714	Intermediate Similarity	NPC189609
0.7714	Intermediate Similarity	NPC471148
0.7714	Intermediate Similarity	NPC303653
0.7714	Intermediate Similarity	NPC291500
0.7708	Intermediate Similarity	NPC474780
0.7706	Intermediate Similarity	NPC50223
0.77	Intermediate Similarity	NPC476705
0.77	Intermediate Similarity	NPC475972
0.77	Intermediate Similarity	NPC303697
0.77	Intermediate Similarity	NPC158061
0.7685	Intermediate Similarity	NPC474664
0.7685	Intermediate Similarity	NPC14862

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 NPC475053 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	187
0.1-0.2	1391
0.2-0.3	3370
0.3-0.4	2645
0.4-0.5	1097
0.5-0.6	381
0.6-0.7	65
0.7-0.8	12
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8526	High Similarity	NPD46	Approved
0.8526	High Similarity	NPD6698	Approved
0.8333	Intermediate Similarity	NPD7838	Discovery
0.7879	Intermediate Similarity	NPD7983	Approved
0.7788	Intermediate Similarity	NPD5344	Discontinued
0.7767	Intermediate Similarity	NPD8029	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD6648	Approved
0.7624	Intermediate Similarity	NPD5779	Approved
0.7624	Intermediate Similarity	NPD5778	Approved
0.7545	Intermediate Similarity	NPD6371	Approved
0.7449	Intermediate Similarity	NPD1733	Clinical (unspecified phase)
0.7364	Intermediate Similarity	NPD6686	Approved
0.7273	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7238	Intermediate Similarity	NPD7839	Suspended
0.7168	Intermediate Similarity	NPD8413	Clinical (unspecified phase)
0.7157	Intermediate Similarity	NPD6101	Approved
0.7157	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7155	Intermediate Similarity	NPD7115	Discovery
0.7103	Intermediate Similarity	NPD4225	Approved
0.7083	Intermediate Similarity	NPD7829	Approved
0.7083	Intermediate Similarity	NPD7830	Approved
0.7059	Intermediate Similarity	NPD8513	Phase 3
0.7059	Intermediate Similarity	NPD8517	Approved
0.7059	Intermediate Similarity	NPD8516	Approved
0.7059	Intermediate Similarity	NPD8515	Approved
0.7019	Intermediate Similarity	NPD6411	Approved
0.6991	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.699	Remote Similarity	NPD1695	Approved
0.6981	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6967	Remote Similarity	NPD8273	Phase 1
0.6923	Remote Similarity	NPD5785	Approved
0.69	Remote Similarity	NPD7154	Phase 3
0.681	Remote Similarity	NPD6053	Discontinued
0.6803	Remote Similarity	NPD7642	Approved
0.6774	Remote Similarity	NPD8074	Phase 3
0.6765	Remote Similarity	NPD5363	Approved
0.6733	Remote Similarity	NPD5362	Discontinued
0.6729	Remote Similarity	NPD5282	Discontinued
0.6727	Remote Similarity	NPD7640	Approved
0.6727	Remote Similarity	NPD7639	Approved
0.6699	Remote Similarity	NPD4249	Approved
0.6698	Remote Similarity	NPD7637	Suspended
0.6667	Remote Similarity	NPD7641	Discontinued
0.6638	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6636	Remote Similarity	NPD7638	Approved
0.6635	Remote Similarity	NPD4250	Approved
0.6635	Remote Similarity	NPD4251	Approved
0.6634	Remote Similarity	NPD5209	Approved
0.6634	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.66	Remote Similarity	NPD4819	Approved
0.66	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.66	Remote Similarity	NPD4820	Approved
0.66	Remote Similarity	NPD4822	Approved
0.66	Remote Similarity	NPD4821	Approved
0.6569	Remote Similarity	NPD6110	Phase 1
0.6565	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.656	Remote Similarity	NPD7507	Approved
0.656	Remote Similarity	NPD8451	Approved
0.6538	Remote Similarity	NPD5786	Approved
0.6522	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6508	Remote Similarity	NPD8448	Approved
0.6504	Remote Similarity	NPD8444	Approved
0.6504	Remote Similarity	NPD7503	Approved
0.648	Remote Similarity	NPD8299	Approved
0.648	Remote Similarity	NPD8340	Approved
0.648	Remote Similarity	NPD8342	Approved
0.648	Remote Similarity	NPD8341	Approved
0.6476	Remote Similarity	NPD7524	Approved
0.6471	Remote Similarity	NPD4632	Approved
0.6471	Remote Similarity	NPD4270	Approved
0.6471	Remote Similarity	NPD4269	Approved
0.6471	Remote Similarity	NPD6435	Approved
0.6466	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6465	Remote Similarity	NPD4756	Discovery
0.6442	Remote Similarity	NPD1694	Approved
0.6441	Remote Similarity	NPD7116	Clinical (unspecified phase)
0.6434	Remote Similarity	NPD7260	Phase 2
0.6429	Remote Similarity	NPD8039	Approved
0.6423	Remote Similarity	NPD6319	Approved
0.6406	Remote Similarity	NPD7319	Approved
0.64	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.64	Remote Similarity	NPD4268	Approved
0.64	Remote Similarity	NPD4271	Approved
0.6383	Remote Similarity	NPD4247	Clinical (unspecified phase)
0.6379	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6379	Remote Similarity	NPD6412	Phase 2
0.6373	Remote Similarity	NPD5369	Approved
0.6357	Remote Similarity	NPD8391	Approved
0.6357	Remote Similarity	NPD8390	Approved
0.6357	Remote Similarity	NPD8392	Approved
0.6311	Remote Similarity	NPD7500	Approved
0.6275	Remote Similarity	NPD4252	Approved
0.6275	Remote Similarity	NPD5368	Approved
0.625	Remote Similarity	NPD5332	Approved
0.625	Remote Similarity	NPD8297	Approved
0.625	Remote Similarity	NPD5331	Approved
0.625	Remote Similarity	NPD6695	Phase 3
0.6239	Remote Similarity	NPD5697	Approved
0.6214	Remote Similarity	NPD4790	Discontinued
0.619	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.619	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6186	Remote Similarity	NPD6899	Approved
0.6186	Remote Similarity	NPD6881	Approved
0.6179	Remote Similarity	NPD7505	Discontinued
0.6179	Remote Similarity	NPD6009	Approved
0.6174	Remote Similarity	NPD7632	Discontinued
0.6154	Remote Similarity	NPD6008	Approved
0.6142	Remote Similarity	NPD7604	Phase 2
0.6134	Remote Similarity	NPD6014	Approved
0.6134	Remote Similarity	NPD6012	Approved
0.6134	Remote Similarity	NPD6013	Approved
0.6132	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6132	Remote Similarity	NPD1696	Phase 3
0.6129	Remote Similarity	NPD7328	Approved
0.6129	Remote Similarity	NPD7327	Approved
0.6121	Remote Similarity	NPD6647	Phase 2
0.6111	Remote Similarity	NPD8033	Approved
0.6111	Remote Similarity	NPD5983	Phase 2
0.6106	Remote Similarity	NPD6083	Phase 2
0.6106	Remote Similarity	NPD6084	Phase 2
0.6094	Remote Similarity	NPD7492	Approved
0.6083	Remote Similarity	NPD6421	Discontinued
0.6083	Remote Similarity	NPD7102	Approved
0.6083	Remote Similarity	NPD6883	Approved
0.6083	Remote Similarity	NPD7290	Approved
0.608	Remote Similarity	NPD7516	Approved
0.6071	Remote Similarity	NPD5695	Phase 3
0.6066	Remote Similarity	NPD8133	Approved
0.605	Remote Similarity	NPD6011	Approved
0.6047	Remote Similarity	NPD6616	Approved
0.6034	Remote Similarity	NPD5211	Phase 2
0.6033	Remote Similarity	NPD6847	Approved
0.6033	Remote Similarity	NPD6617	Approved
0.6033	Remote Similarity	NPD8130	Phase 1
0.6033	Remote Similarity	NPD6650	Approved
0.6033	Remote Similarity	NPD6649	Approved
0.6033	Remote Similarity	NPD6869	Approved
0.6032	Remote Similarity	NPD8294	Approved
0.6032	Remote Similarity	NPD8377	Approved
0.6032	Remote Similarity	NPD6054	Approved
0.6019	Remote Similarity	NPD3573	Approved
0.6019	Remote Similarity	NPD7750	Discontinued
0.6018	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.6017	Remote Similarity	NPD5048	Discontinued
0.6017	Remote Similarity	NPD5739	Approved
0.6017	Remote Similarity	NPD6675	Approved
0.6017	Remote Similarity	NPD6402	Approved
0.6017	Remote Similarity	NPD7128	Approved
0.6016	Remote Similarity	NPD8328	Phase 3
0.6015	Remote Similarity	NPD6845	Suspended
0.6	Remote Similarity	NPD7078	Approved
0.5984	Remote Similarity	NPD8380	Approved
0.5984	Remote Similarity	NPD6015	Approved
0.5984	Remote Similarity	NPD8379	Approved
0.5984	Remote Similarity	NPD8378	Approved
0.5984	Remote Similarity	NPD6882	Approved
0.5984	Remote Similarity	NPD6016	Approved
0.5984	Remote Similarity	NPD8296	Approved
0.5984	Remote Similarity	NPD8335	Approved
0.5982	Remote Similarity	NPD7748	Approved
0.5968	Remote Similarity	NPD2629	Approved
0.5966	Remote Similarity	NPD5701	Approved
0.5962	Remote Similarity	NPD7332	Phase 2
0.5962	Remote Similarity	NPD6930	Phase 2
0.5962	Remote Similarity	NPD6931	Approved
0.5962	Remote Similarity	NPD7514	Phase 3
0.5954	Remote Similarity	NPD7736	Approved
0.595	Remote Similarity	NPD4634	Approved
0.5946	Remote Similarity	NPD7515	Phase 2
0.5946	Remote Similarity	NPD5281	Approved
0.5946	Remote Similarity	NPD5284	Approved
0.5938	Remote Similarity	NPD6370	Approved
0.5938	Remote Similarity	NPD7331	Phase 2
0.5938	Remote Similarity	NPD7623	Phase 3
0.5938	Remote Similarity	NPD5988	Approved
0.5938	Remote Similarity	NPD7624	Clinical (unspecified phase)
0.5932	Remote Similarity	NPD5141	Approved
0.5926	Remote Similarity	NPD6422	Discontinued
0.5926	Remote Similarity	NPD5279	Phase 3
0.5923	Remote Similarity	NPD6336	Discontinued
0.5917	Remote Similarity	NPD7320	Approved
0.5915	Remote Similarity	NPD4628	Phase 3
0.5914	Remote Similarity	NPD4246	Clinical (unspecified phase)
0.5913	Remote Similarity	NPD5696	Approved
0.5906	Remote Similarity	NPD7299	Clinical (unspecified phase)
0.5905	Remote Similarity	NPD6902	Approved
0.5895	Remote Similarity	NPD3197	Phase 1
0.5893	Remote Similarity	NPD6399	Phase 3
0.5868	Remote Similarity	NPD6373	Approved
0.5868	Remote Similarity	NPD6372	Approved
0.5868	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.5865	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.5865	Remote Similarity	NPD6929	Approved
0.5862	Remote Similarity	NPD5286	Approved
0.5862	Remote Similarity	NPD4696	Approved
0.5862	Remote Similarity	NPD5285	Approved
0.5859	Remote Similarity	NPD6921	Approved
0.5859	Remote Similarity	NPD7739	Clinical (unspecified phase)
0.5856	Remote Similarity	NPD3168	Discontinued
0.584	Remote Similarity	NPD690	Clinical (unspecified phase)

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