NPASS Compound

Structure

NPC471492 OpenBabel07101719522D 26 28 0 0 1 0 0 0 0 0999 V2000 -2.0718 3.2910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2104 -1.5035 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0515 2.6701 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6138 0.1803 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2728 -0.5819 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5831 0.2704 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5711 -0.9071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5711 1.8724 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2963 1.2096 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9789 2.9609 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7020 0.4490 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4071 -0.4244 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4071 1.3897 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.7372 0.4827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9680 -0.4789 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6205 -0.7395 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.6205 1.7048 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 0.9653 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.7184 3.5813 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.8751 -0.8091 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.6205 2.6701 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0392 1.9298 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.2522 1.0753 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.1466 2.0102 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.1678 -1.0187 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 10 1 0 0 0 0 3 17 1 0 0 0 0 4 23 1 0 0 0 0 5 6 1 0 0 0 0 5 16 1 0 0 0 0 6 18 1 0 0 0 0 7 12 2 0 0 0 0 7 16 1 0 0 0 0 8 13 1 0 0 0 0 8 17 1 0 0 0 0 9 11 1 0 0 0 0 9 23 1 0 0 0 0 10 19 2 0 0 0 0 10 24 1 0 0 0 0 11 14 2 0 0 0 0 11 15 1 0 0 0 0 12 14 1 0 0 0 0 12 25 1 0 0 0 0 13 14 1 0 0 0 0 13 24 1 1 0 0 0 15 20 2 0 0 0 0 15 25 1 0 0 0 0 16 2 1 1 0 0 0 16 26 1 0 0 0 0 17 18 1 6 0 0 0 17 21 1 0 0 0 0 18 22 1 1 0 0 0 18 26 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	368.15
Volume:	353.991
LogP:	1.259
LogD:	1.377
LogS:	-2.444
# Rotatable Bonds:	4
TPSA:	118.59
# H-Bond Aceptor:	8
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.638
Synthetic Accessibility Score:	5.992
Fsp3:	0.611
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:	-5.368
MDCK Permeability:	2.7578542358241975e-05
Pgp-inhibitor:	0.009
Pgp-substrate:	0.542
Human Intestinal Absorption (HIA):	0.034
20% Bioavailability (F20%):	0.903
30% Bioavailability (F30%):	0.989

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.691
Plasma Protein Binding (PPB):	66.5108871459961%
Volume Distribution (VD):	0.635
Pgp-substrate:	35.32181930541992%

ADMET: Metabolism

CYP1A2-inhibitor:	0.024
CYP1A2-substrate:	0.977
CYP2C19-inhibitor:	0.021
CYP2C19-substrate:	0.216
CYP2C9-inhibitor:	0.039
CYP2C9-substrate:	0.051
CYP2D6-inhibitor:	0.004
CYP2D6-substrate:	0.114
CYP3A4-inhibitor:	0.165
CYP3A4-substrate:	0.457

ADMET: Excretion

Clearance (CL):	8.238
Half-life (T1/2):	0.857

ADMET: Toxicity

hERG Blockers:	0.001
Human Hepatotoxicity (H-HT):	0.885
Drug-inuced Liver Injury (DILI):	0.97
AMES Toxicity:	0.164
Rat Oral Acute Toxicity:	0.152
Maximum Recommended Daily Dose:	0.269
Skin Sensitization:	0.785
Carcinogencity:	0.952
Eye Corrosion:	0.184
Eye Irritation:	0.035
Respiratory Toxicity:	0.976

Download Data

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

Natural Product: NPC471492

Natural Product ID:	NPC471492
*Common Name:**	OPAWQGXUUDQIPB-SFNIKPSXSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	OPAWQGXUUDQIPB-SFNIKPSXSA-N
Standard InCHI:	InChI=1S/C18H24O8/c1-10(19)24-13-8-17(3,21)18(22)6-5-16(2,26-18)7-12-14(13)11(9-23-4)15(20)25-12/h7,13,21-22H,5-6,8-9H2,1-4H3/b12-7+/t13-,16+,17-,18-/m0/s1
SMILES:	CC(=O)OC1CC(C2(CCC(O2)(C=C3C1=C(C(=O)O3)COC)C)O)(C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL252919
PubChem CID:	44445365
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001983] Dihydrofurans [CHEMONTID:0001982] Furanones [CHEMONTID:0002223] Butenolides

*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
NPO32710	pseudoelephantopus spicatus	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[17970595]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	3

Activity Type	# Activity
Cell Line	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT65	Cell Line	HepG2	Homo sapiens	IC50	>	5.0	ug.mL-1	PMID[513896]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	IC50	>	5.0	ug.mL-1	PMID[513896]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	5.0	ug.mL-1	PMID[513896]

☑ 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 NPC471492 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	201
0.1-0.2	1302
0.2-0.3	4678
0.3-0.4	9395
0.4-0.5	16483
0.5-0.6	7407
0.6-0.7	2866
0.7-0.8	338
0.8-0.85	5
0.85-0.9	11
0.9-0.95	4
0.95-1	7

Similarity Score	Similarity Level	Natural Product ID
0.9778	High Similarity	NPC471490
0.9778	High Similarity	NPC2666
0.9667	High Similarity	NPC473333
0.9011	High Similarity	NPC175842
0.9011	High Similarity	NPC32494
0.8901	High Similarity	NPC3436
0.8804	High Similarity	NPC470520
0.8791	High Similarity	NPC225283
0.871	High Similarity	NPC59646
0.8617	High Similarity	NPC470521
0.8587	High Similarity	NPC64913
0.8587	High Similarity	NPC242877
0.8511	High Similarity	NPC471483
0.8252	Intermediate Similarity	NPC38154
0.8163	Intermediate Similarity	NPC471462
0.8085	Intermediate Similarity	NPC260343
0.8081	Intermediate Similarity	NPC187268
0.7857	Intermediate Similarity	NPC474338
0.7843	Intermediate Similarity	NPC291500
0.7843	Intermediate Similarity	NPC303653
0.7843	Intermediate Similarity	NPC197835
0.7843	Intermediate Similarity	NPC189609
0.7843	Intermediate Similarity	NPC140591
0.7835	Intermediate Similarity	NPC158061
0.7745	Intermediate Similarity	NPC219038
0.7745	Intermediate Similarity	NPC98859
0.7745	Intermediate Similarity	NPC4637
0.77	Intermediate Similarity	NPC288350
0.77	Intermediate Similarity	NPC301596
0.77	Intermediate Similarity	NPC299396
0.77	Intermediate Similarity	NPC173329
0.7684	Intermediate Similarity	NPC204048
0.7677	Intermediate Similarity	NPC256368
0.767	Intermediate Similarity	NPC471599
0.76	Intermediate Similarity	NPC471141
0.7576	Intermediate Similarity	NPC272293
0.7576	Intermediate Similarity	NPC40821
0.7576	Intermediate Similarity	NPC476300
0.7576	Intermediate Similarity	NPC32862
0.7551	Intermediate Similarity	NPC177668
0.7551	Intermediate Similarity	NPC118078
0.7549	Intermediate Similarity	NPC151093
0.7549	Intermediate Similarity	NPC203627
0.7525	Intermediate Similarity	NPC172998
0.75	Intermediate Similarity	NPC311163
0.75	Intermediate Similarity	NPC149371
0.7477	Intermediate Similarity	NPC473807
0.7476	Intermediate Similarity	NPC244878
0.7475	Intermediate Similarity	NPC327760
0.7453	Intermediate Similarity	NPC239961
0.7451	Intermediate Similarity	NPC218064
0.7451	Intermediate Similarity	NPC199099
0.7449	Intermediate Similarity	NPC133450
0.7449	Intermediate Similarity	NPC473564
0.7426	Intermediate Similarity	NPC36954
0.7426	Intermediate Similarity	NPC234339
0.7426	Intermediate Similarity	NPC273197
0.7426	Intermediate Similarity	NPC220221
0.7404	Intermediate Similarity	NPC474339
0.7404	Intermediate Similarity	NPC164598
0.7404	Intermediate Similarity	NPC20673
0.7404	Intermediate Similarity	NPC47880
0.74	Intermediate Similarity	NPC81419
0.74	Intermediate Similarity	NPC238090
0.74	Intermediate Similarity	NPC179746
0.74	Intermediate Similarity	NPC472195
0.74	Intermediate Similarity	NPC472196
0.74	Intermediate Similarity	NPC475098
0.74	Intermediate Similarity	NPC189651
0.74	Intermediate Similarity	NPC475912
0.7396	Intermediate Similarity	NPC471494
0.7396	Intermediate Similarity	NPC130030
0.7387	Intermediate Similarity	NPC106446
0.7383	Intermediate Similarity	NPC26617
0.7379	Intermediate Similarity	NPC475068
0.7379	Intermediate Similarity	NPC473326
0.7379	Intermediate Similarity	NPC471144
0.7374	Intermediate Similarity	NPC474323
0.7374	Intermediate Similarity	NPC51004
0.7374	Intermediate Similarity	NPC206614
0.7374	Intermediate Similarity	NPC80875
0.7374	Intermediate Similarity	NPC473904
0.7358	Intermediate Similarity	NPC100487
0.7353	Intermediate Similarity	NPC98165
0.7353	Intermediate Similarity	NPC230800
0.7353	Intermediate Similarity	NPC279621
0.7347	Intermediate Similarity	NPC280621
0.7347	Intermediate Similarity	NPC233551
0.7347	Intermediate Similarity	NPC40376
0.7347	Intermediate Similarity	NPC21208
0.7347	Intermediate Similarity	NPC20339
0.7347	Intermediate Similarity	NPC48338
0.734	Intermediate Similarity	NPC474894
0.7333	Intermediate Similarity	NPC472754
0.7327	Intermediate Similarity	NPC159698
0.732	Intermediate Similarity	NPC469483
0.732	Intermediate Similarity	NPC61527
0.7315	Intermediate Similarity	NPC50124
0.7308	Intermediate Similarity	NPC288876
0.73	Intermediate Similarity	NPC303230
0.73	Intermediate Similarity	NPC6099
0.73	Intermediate Similarity	NPC114345
0.73	Intermediate Similarity	NPC12172
0.73	Intermediate Similarity	NPC184463
0.73	Intermediate Similarity	NPC208886
0.73	Intermediate Similarity	NPC30515
0.7292	Intermediate Similarity	NPC475706
0.729	Intermediate Similarity	NPC82251
0.7282	Intermediate Similarity	NPC266842
0.7282	Intermediate Similarity	NPC153559
0.7273	Intermediate Similarity	NPC307411
0.7273	Intermediate Similarity	NPC14901
0.7273	Intermediate Similarity	NPC139418
0.7273	Intermediate Similarity	NPC130359
0.7264	Intermediate Similarity	NPC475871
0.7264	Intermediate Similarity	NPC475945
0.7264	Intermediate Similarity	NPC472755
0.7255	Intermediate Similarity	NPC107476
0.7255	Intermediate Similarity	NPC270013
0.7255	Intermediate Similarity	NPC475659
0.7255	Intermediate Similarity	NPC471142
0.7255	Intermediate Similarity	NPC14961
0.7245	Intermediate Similarity	NPC191283
0.7245	Intermediate Similarity	NPC475037
0.7245	Intermediate Similarity	NPC178215
0.7245	Intermediate Similarity	NPC160138
0.7241	Intermediate Similarity	NPC287236
0.7238	Intermediate Similarity	NPC474742
0.7238	Intermediate Similarity	NPC473332
0.7238	Intermediate Similarity	NPC198992
0.7238	Intermediate Similarity	NPC472753
0.7228	Intermediate Similarity	NPC212486
0.7228	Intermediate Similarity	NPC156553
0.7222	Intermediate Similarity	NPC474285
0.7222	Intermediate Similarity	NPC477513
0.7222	Intermediate Similarity	NPC475074
0.7222	Intermediate Similarity	NPC254538
0.7216	Intermediate Similarity	NPC471185
0.7216	Intermediate Similarity	NPC477013
0.7216	Intermediate Similarity	NPC475034
0.7216	Intermediate Similarity	NPC329838
0.7216	Intermediate Similarity	NPC471567
0.7216	Intermediate Similarity	NPC11804
0.7216	Intermediate Similarity	NPC329615
0.7216	Intermediate Similarity	NPC477014
0.7216	Intermediate Similarity	NPC120398
0.7212	Intermediate Similarity	NPC161855
0.7212	Intermediate Similarity	NPC90819
0.7212	Intermediate Similarity	NPC473307
0.7212	Intermediate Similarity	NPC124181
0.7207	Intermediate Similarity	NPC66108
0.7204	Intermediate Similarity	NPC3852
0.72	Intermediate Similarity	NPC471184
0.72	Intermediate Similarity	NPC239517
0.72	Intermediate Similarity	NPC478003
0.72	Intermediate Similarity	NPC476004
0.72	Intermediate Similarity	NPC474761
0.72	Intermediate Similarity	NPC478004
0.72	Intermediate Similarity	NPC474232
0.72	Intermediate Similarity	NPC158388
0.72	Intermediate Similarity	NPC471569
0.72	Intermediate Similarity	NPC473448
0.7196	Intermediate Similarity	NPC474741
0.7196	Intermediate Similarity	NPC472748
0.7196	Intermediate Similarity	NPC203659
0.7196	Intermediate Similarity	NPC472756
0.7196	Intermediate Similarity	NPC146731
0.7196	Intermediate Similarity	NPC474917
0.7188	Intermediate Similarity	NPC475714
0.7188	Intermediate Similarity	NPC231601
0.7184	Intermediate Similarity	NPC476315
0.7184	Intermediate Similarity	NPC472995
0.7184	Intermediate Similarity	NPC473859
0.7182	Intermediate Similarity	NPC177047
0.7182	Intermediate Similarity	NPC235014
0.7172	Intermediate Similarity	NPC202672
0.7172	Intermediate Similarity	NPC473905
0.7172	Intermediate Similarity	NPC89001
0.7172	Intermediate Similarity	NPC320458
0.717	Intermediate Similarity	NPC86077
0.717	Intermediate Similarity	NPC471148
0.717	Intermediate Similarity	NPC474747
0.717	Intermediate Similarity	NPC472552
0.717	Intermediate Similarity	NPC183571
0.7158	Intermediate Similarity	NPC8538
0.7158	Intermediate Similarity	NPC184208
0.7157	Intermediate Similarity	NPC473316
0.7157	Intermediate Similarity	NPC472198
0.7157	Intermediate Similarity	NPC140543
0.7157	Intermediate Similarity	NPC474247
0.7157	Intermediate Similarity	NPC474035
0.7157	Intermediate Similarity	NPC81386
0.7157	Intermediate Similarity	NPC477131
0.7157	Intermediate Similarity	NPC471496
0.7157	Intermediate Similarity	NPC473330
0.7157	Intermediate Similarity	NPC477241
0.7156	Intermediate Similarity	NPC475960
0.7156	Intermediate Similarity	NPC193765
0.7156	Intermediate Similarity	NPC38948
0.7156	Intermediate Similarity	NPC181994

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 NPC471492 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	186
0.1-0.2	1756
0.2-0.3	3785
0.3-0.4	2374
0.4-0.5	826
0.5-0.6	174
0.6-0.7	47
0.7-0.8	2
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
0.7732	Intermediate Similarity	NPD7838	Discovery
0.7383	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7212	Intermediate Similarity	NPD8029	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD46	Approved
0.72	Intermediate Similarity	NPD6698	Approved
0.7129	Intermediate Similarity	NPD7983	Approved
0.6847	Remote Similarity	NPD6686	Approved
0.6729	Remote Similarity	NPD4225	Approved
0.6726	Remote Similarity	NPD6371	Approved
0.6667	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5282	Discontinued
0.6667	Remote Similarity	NPD6648	Approved
0.6634	Remote Similarity	NPD4249	Approved
0.6606	Remote Similarity	NPD5344	Discontinued
0.6583	Remote Similarity	NPD7503	Approved
0.6583	Remote Similarity	NPD8515	Approved
0.6583	Remote Similarity	NPD8513	Phase 3
0.6583	Remote Similarity	NPD8517	Approved
0.6583	Remote Similarity	NPD8516	Approved
0.6569	Remote Similarity	NPD4251	Approved
0.6569	Remote Similarity	NPD4250	Approved
0.6471	Remote Similarity	NPD7328	Approved
0.6471	Remote Similarity	NPD7327	Approved
0.6449	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6446	Remote Similarity	NPD8033	Approved
0.6436	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6417	Remote Similarity	NPD7516	Approved
0.6389	Remote Similarity	NPD7839	Suspended
0.6373	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD8294	Approved
0.6364	Remote Similarity	NPD8377	Approved
0.6349	Remote Similarity	NPD7319	Approved
0.6325	Remote Similarity	NPD6053	Discontinued
0.632	Remote Similarity	NPD8074	Phase 3
0.6311	Remote Similarity	NPD8296	Approved
0.6311	Remote Similarity	NPD8380	Approved
0.6311	Remote Similarity	NPD8335	Approved
0.6311	Remote Similarity	NPD8379	Approved
0.6311	Remote Similarity	NPD8378	Approved
0.6286	Remote Similarity	NPD1695	Approved
0.6264	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6262	Remote Similarity	NPD5778	Approved
0.6262	Remote Similarity	NPD5779	Approved
0.624	Remote Similarity	NPD7507	Approved
0.621	Remote Similarity	NPD7829	Approved
0.621	Remote Similarity	NPD7830	Approved
0.6207	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6176	Remote Similarity	NPD7154	Phase 3
0.6168	Remote Similarity	NPD7637	Suspended
0.6154	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6136	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6129	Remote Similarity	NPD8080	Discontinued
0.6116	Remote Similarity	NPD7505	Discontinued
0.6116	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.6111	Remote Similarity	NPD8451	Approved
0.608	Remote Similarity	NPD7642	Approved
0.6078	Remote Similarity	NPD5209	Approved
0.6063	Remote Similarity	NPD8448	Approved
0.6058	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6048	Remote Similarity	NPD8444	Approved
0.5984	Remote Similarity	NPD8273	Phase 1
0.5984	Remote Similarity	NPD7500	Approved
0.5982	Remote Similarity	NPD7638	Approved
0.5966	Remote Similarity	NPD2204	Approved
0.5943	Remote Similarity	NPD7524	Approved
0.5929	Remote Similarity	NPD7640	Approved
0.5929	Remote Similarity	NPD7639	Approved
0.5926	Remote Similarity	NPD5785	Approved
0.5923	Remote Similarity	NPD8391	Approved
0.5923	Remote Similarity	NPD8390	Approved
0.5923	Remote Similarity	NPD8392	Approved
0.592	Remote Similarity	NPD8274	Clinical (unspecified phase)
0.5917	Remote Similarity	NPD969	Suspended
0.5906	Remote Similarity	NPD8341	Approved
0.5906	Remote Similarity	NPD8342	Approved
0.5906	Remote Similarity	NPD8340	Approved
0.5906	Remote Similarity	NPD8299	Approved
0.5897	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.5882	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.5882	Remote Similarity	NPD4822	Approved
0.5882	Remote Similarity	NPD4820	Approved
0.5882	Remote Similarity	NPD4819	Approved
0.5882	Remote Similarity	NPD4821	Approved
0.5854	Remote Similarity	NPD7115	Discovery
0.5833	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.5833	Remote Similarity	NPD6101	Approved
0.581	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.5806	Remote Similarity	NPD7641	Discontinued
0.5781	Remote Similarity	NPD7492	Approved
0.5769	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.5763	Remote Similarity	NPD6412	Phase 2
0.5755	Remote Similarity	NPD5363	Approved
0.575	Remote Similarity	NPD2067	Discontinued
0.5743	Remote Similarity	NPD4756	Discovery
0.5736	Remote Similarity	NPD6616	Approved
0.5727	Remote Similarity	NPD6411	Approved
0.5714	Remote Similarity	NPD6059	Approved
0.5714	Remote Similarity	NPD6110	Phase 1
0.5714	Remote Similarity	NPD6845	Suspended
0.5714	Remote Similarity	NPD6695	Phase 3
0.5714	Remote Similarity	NPD5362	Discontinued
0.5714	Remote Similarity	NPD6054	Approved
0.5714	Remote Similarity	NPD6319	Approved
0.5692	Remote Similarity	NPD7078	Approved
0.5692	Remote Similarity	NPD8293	Discontinued
0.5686	Remote Similarity	NPD4268	Approved
0.5686	Remote Similarity	NPD4271	Approved
0.5678	Remote Similarity	NPD4211	Phase 1
0.5673	Remote Similarity	NPD5369	Approved
0.5669	Remote Similarity	NPD6015	Approved
0.5669	Remote Similarity	NPD6016	Approved
0.5649	Remote Similarity	NPD7736	Approved
0.5639	Remote Similarity	NPD7260	Phase 2
0.5636	Remote Similarity	NPD3168	Discontinued
0.5625	Remote Similarity	NPD6370	Approved
0.5625	Remote Similarity	NPD5988	Approved
0.5619	Remote Similarity	NPD4269	Approved
0.5619	Remote Similarity	NPD4270	Approved
0.561	Remote Similarity	NPD8133	Approved
0.5607	Remote Similarity	NPD1694	Approved
0.5604	Remote Similarity	NPD9119	Approved
0.5604	Remote Similarity	NPD69	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