NPASS Compound

Structure

NPC471447 OpenBabel07101718202D 23 24 0 0 1 0 0 0 0 0999 V2000 -1.4894 -2.1160 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5827 -0.3364 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0827 -1.2024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9135 0.4067 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -0.1045 -0.9945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -2.5000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -4.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.1215 1.3849 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.6386 -1.6637 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 14 1 0 0 0 0 2 3 2 0 0 0 0 2 4 1 0 0 0 0 3 7 1 0 0 0 0 4 8 2 0 0 0 0 5 6 1 0 0 0 0 5 11 1 0 0 0 0 6 12 1 0 0 0 0 7 15 2 0 0 0 0 8 15 1 0 0 0 0 9 10 2 0 0 0 0 9 15 1 0 0 0 0 10 16 1 0 0 0 0 11 19 1 0 0 0 0 12 20 1 0 0 0 0 13 14 2 0 0 0 0 13 17 1 0 0 0 0 14 18 1 0 0 0 0 16 19 2 3 0 0 0 16 21 1 0 0 0 0 17 20 1 0 0 0 0 17 22 1 0 0 0 0 18 20 1 0 0 0 0 18 23 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	314.16
Volume:	332.68
LogP:	2.455
LogD:	2.555
LogS:	-3.148
# Rotatable Bonds:	8
TPSA:	74.49
# H-Bond Aceptor:	5
# H-Bond Donor:	3
# Rings:	2
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.543
Synthetic Accessibility Score:	2.459
Fsp3:	0.278
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:	-4.89
MDCK Permeability:	1.9870562027790584e-05
Pgp-inhibitor:	0.015
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.015
20% Bioavailability (F20%):	0.976
30% Bioavailability (F30%):	0.979

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.203
Plasma Protein Binding (PPB):	91.65535736083984%
Volume Distribution (VD):	0.626
Pgp-substrate:	7.441593647003174%

ADMET: Metabolism

CYP1A2-inhibitor:	0.831
CYP1A2-substrate:	0.081
CYP2C19-inhibitor:	0.383
CYP2C19-substrate:	0.057
CYP2C9-inhibitor:	0.609
CYP2C9-substrate:	0.974
CYP2D6-inhibitor:	0.615
CYP2D6-substrate:	0.868
CYP3A4-inhibitor:	0.206
CYP3A4-substrate:	0.141

ADMET: Excretion

Clearance (CL):	8.319
Half-life (T1/2):	0.846

ADMET: Toxicity

hERG Blockers:	0.021
Human Hepatotoxicity (H-HT):	0.444
Drug-inuced Liver Injury (DILI):	0.434
AMES Toxicity:	0.034
Rat Oral Acute Toxicity:	0.039
Maximum Recommended Daily Dose:	0.071
Skin Sensitization:	0.836
Carcinogencity:	0.225
Eye Corrosion:	0.005
Eye Irritation:	0.293
Respiratory Toxicity:	0.285

Download Data

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

Natural Product: NPC471447

Natural Product ID:	NPC471447
*Common Name:**	Gigantamide A
IUPAC Name:	(E)-N-[4-(2-hydroxy-4-methyl-5-oxo-2H-pyrrol-1-yl)butyl]-3-phenylprop-2-enamide
Synonyms:
Standard InCHIKey:	BJWYJZGECNLLCG-MDZDMXLPSA-N
Standard InCHI:	InChI=1S/C18H22N2O3/c1-14-13-17(22)20(18(14)23)12-6-5-11-19-16(21)10-9-15-7-3-2-4-8-15/h2-4,7-10,13,17,22H,5-6,11-12H2,1H3,(H,19,21)/b10-9+
SMILES:	OC1C=C(C(=O)N1CCCCN=C(/C=C/c1ccccc1)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL249250
PubChem CID:	23655945
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000476] Cinnamic acids and derivatives [CHEMONTID:0002810] Cinnamic acid amides

*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
NPO3333	Aglaia gigantea	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17880174]
NPO4720	Aglaia perviridis	Species	Meliaceae	Eukaryota	leaves, twigs, and fruits	Nui Chua National Park (11 43' N; 109 08' E; 730 m alt.), Ninh Thuan Province, Vietnam	2010-Jan	PMID[23301897]
NPO4720	Aglaia perviridis	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31621322]
NPO3333	Aglaia gigantea	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4720	Aglaia perviridis	Species	Meliaceae	Eukaryota	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
ED50	2

Activity Type	# Activity
Cell Line	1
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT139	Cell Line	HT-29	Homo sapiens	ED50	>	10.0	uM	PMID[532233]
NPT721	Individual Protein	Nuclear factor NF-kappa-B p65 subunit	Homo sapiens	ED50	>	20.0	uM	PMID[532233]

☑ 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 NPC471447 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	80
0.1-0.2	2206
0.2-0.3	7907
0.3-0.4	18132
0.4-0.5	11963
0.5-0.6	2044
0.6-0.7	341
0.7-0.8	14
0.8-0.85	8
0.85-0.9	1
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8273	Intermediate Similarity	NPC475013
0.8224	Intermediate Similarity	NPC143516
0.8148	Intermediate Similarity	NPC45033
0.8148	Intermediate Similarity	NPC474804
0.8148	Intermediate Similarity	NPC130898
0.8148	Intermediate Similarity	NPC474973
0.8125	Intermediate Similarity	NPC476048
0.7961	Intermediate Similarity	NPC474974
0.7838	Intermediate Similarity	NPC473676
0.7549	Intermediate Similarity	NPC305602
0.7549	Intermediate Similarity	NPC17497
0.7458	Intermediate Similarity	NPC239357
0.7455	Intermediate Similarity	NPC329375
0.74	Intermediate Similarity	NPC14326
0.7379	Intermediate Similarity	NPC473031
0.7353	Intermediate Similarity	NPC3210
0.7222	Intermediate Similarity	NPC256452
0.7196	Intermediate Similarity	NPC473661
0.719	Intermediate Similarity	NPC220698
0.7154	Intermediate Similarity	NPC202521
0.7115	Intermediate Similarity	NPC203076
0.7091	Intermediate Similarity	NPC472258
0.7073	Intermediate Similarity	NPC476990
0.7059	Intermediate Similarity	NPC35850
0.7059	Intermediate Similarity	NPC276949
0.7054	Intermediate Similarity	NPC469457
0.704	Intermediate Similarity	NPC6975
0.7031	Intermediate Similarity	NPC213969
0.7031	Intermediate Similarity	NPC165726
0.7	Intermediate Similarity	NPC33742
0.696	Remote Similarity	NPC252878
0.6935	Remote Similarity	NPC27833
0.693	Remote Similarity	NPC202613
0.6905	Remote Similarity	NPC46427
0.6899	Remote Similarity	NPC469666
0.6885	Remote Similarity	NPC470544
0.685	Remote Similarity	NPC22746
0.6829	Remote Similarity	NPC470545
0.68	Remote Similarity	NPC200964
0.6789	Remote Similarity	NPC245259
0.6786	Remote Similarity	NPC33168
0.6774	Remote Similarity	NPC470546
0.6772	Remote Similarity	NPC175726
0.6772	Remote Similarity	NPC474082
0.6752	Remote Similarity	NPC191215
0.6752	Remote Similarity	NPC274089
0.6748	Remote Similarity	NPC315276
0.6748	Remote Similarity	NPC14672
0.6748	Remote Similarity	NPC285926
0.6729	Remote Similarity	NPC53492
0.6727	Remote Similarity	NPC265521
0.6716	Remote Similarity	NPC473360
0.6692	Remote Similarity	NPC319766
0.6667	Remote Similarity	NPC477248
0.6667	Remote Similarity	NPC256689
0.6667	Remote Similarity	NPC473418
0.6667	Remote Similarity	NPC123011
0.6667	Remote Similarity	NPC130309
0.6667	Remote Similarity	NPC477249
0.6639	Remote Similarity	NPC182549
0.6639	Remote Similarity	NPC114741
0.6619	Remote Similarity	NPC201244
0.6619	Remote Similarity	NPC477217
0.6617	Remote Similarity	NPC32858
0.6617	Remote Similarity	NPC325479
0.6617	Remote Similarity	NPC246079
0.6617	Remote Similarity	NPC194857
0.6614	Remote Similarity	NPC71684
0.6607	Remote Similarity	NPC58674
0.6606	Remote Similarity	NPC470877
0.6585	Remote Similarity	NPC246904
0.6581	Remote Similarity	NPC275467
0.6574	Remote Similarity	NPC471638
0.6571	Remote Similarity	NPC314358
0.6567	Remote Similarity	NPC287401
0.6565	Remote Similarity	NPC218323
0.6557	Remote Similarity	NPC273814
0.6555	Remote Similarity	NPC55529
0.6547	Remote Similarity	NPC314388
0.6547	Remote Similarity	NPC315283
0.6545	Remote Similarity	NPC141139
0.6545	Remote Similarity	NPC78041
0.6545	Remote Similarity	NPC471307
0.6545	Remote Similarity	NPC121872
0.6545	Remote Similarity	NPC159178
0.6545	Remote Similarity	NPC74936
0.6545	Remote Similarity	NPC172128
0.6545	Remote Similarity	NPC209764
0.6541	Remote Similarity	NPC120251
0.6535	Remote Similarity	NPC32203
0.6535	Remote Similarity	NPC206800
0.6532	Remote Similarity	NPC188010
0.6532	Remote Similarity	NPC235421
0.6529	Remote Similarity	NPC323007
0.6525	Remote Similarity	NPC211551
0.6525	Remote Similarity	NPC135121
0.6519	Remote Similarity	NPC141050
0.6518	Remote Similarity	NPC71140
0.6515	Remote Similarity	NPC116057
0.6515	Remote Similarity	NPC150863
0.6514	Remote Similarity	NPC262393
0.6514	Remote Similarity	NPC12429
0.6512	Remote Similarity	NPC477163
0.6509	Remote Similarity	NPC474088
0.6505	Remote Similarity	NPC50192
0.65	Remote Similarity	NPC316008
0.65	Remote Similarity	NPC471680
0.65	Remote Similarity	NPC313867
0.6496	Remote Similarity	NPC471317
0.6496	Remote Similarity	NPC77992
0.6475	Remote Similarity	NPC275410
0.6466	Remote Similarity	NPC214200
0.6466	Remote Similarity	NPC228400
0.6462	Remote Similarity	NPC285394
0.6446	Remote Similarity	NPC292758
0.6446	Remote Similarity	NPC65855
0.6442	Remote Similarity	NPC469894
0.6441	Remote Similarity	NPC224610
0.6441	Remote Similarity	NPC113326
0.6441	Remote Similarity	NPC194390
0.6441	Remote Similarity	NPC88267
0.6429	Remote Similarity	NPC239931
0.6429	Remote Similarity	NPC78954
0.6429	Remote Similarity	NPC82770
0.6423	Remote Similarity	NPC43755
0.6422	Remote Similarity	NPC198747
0.6412	Remote Similarity	NPC101719
0.6412	Remote Similarity	NPC171372
0.6412	Remote Similarity	NPC474479
0.6406	Remote Similarity	NPC302169
0.6404	Remote Similarity	NPC30361
0.6404	Remote Similarity	NPC3371
0.6404	Remote Similarity	NPC25565
0.64	Remote Similarity	NPC326200
0.6397	Remote Similarity	NPC248283
0.6396	Remote Similarity	NPC316108
0.6391	Remote Similarity	NPC472413
0.6391	Remote Similarity	NPC17374
0.6391	Remote Similarity	NPC473322
0.6389	Remote Similarity	NPC7817
0.6389	Remote Similarity	NPC475168
0.6387	Remote Similarity	NPC167336
0.6385	Remote Similarity	NPC472415
0.6372	Remote Similarity	NPC471309
0.6364	Remote Similarity	NPC325441
0.6364	Remote Similarity	NPC476249
0.6357	Remote Similarity	NPC473051
0.6357	Remote Similarity	NPC473050
0.6348	Remote Similarity	NPC473501
0.6348	Remote Similarity	NPC475439
0.6343	Remote Similarity	NPC300315
0.6343	Remote Similarity	NPC472245
0.6343	Remote Similarity	NPC200589
0.6343	Remote Similarity	NPC280807
0.6338	Remote Similarity	NPC473804
0.6336	Remote Similarity	NPC222466
0.6333	Remote Similarity	NPC473498
0.6324	Remote Similarity	NPC328070
0.6321	Remote Similarity	NPC303245
0.6321	Remote Similarity	NPC231986
0.6316	Remote Similarity	NPC303045
0.6316	Remote Similarity	NPC161972
0.6311	Remote Similarity	NPC271642
0.6311	Remote Similarity	NPC470127
0.6308	Remote Similarity	NPC474862
0.6304	Remote Similarity	NPC471265
0.6304	Remote Similarity	NPC471264
0.6296	Remote Similarity	NPC255447
0.6294	Remote Similarity	NPC311658
0.6294	Remote Similarity	NPC119569
0.6288	Remote Similarity	NPC472414
0.6286	Remote Similarity	NPC78517
0.6286	Remote Similarity	NPC150712
0.6286	Remote Similarity	NPC167577
0.6281	Remote Similarity	NPC142297
0.6279	Remote Similarity	NPC190663
0.6279	Remote Similarity	NPC80150
0.6277	Remote Similarity	NPC169766
0.6276	Remote Similarity	NPC473491
0.6271	Remote Similarity	NPC318154
0.6269	Remote Similarity	NPC81092
0.6269	Remote Similarity	NPC103605
0.6269	Remote Similarity	NPC111428
0.6268	Remote Similarity	NPC266741
0.6261	Remote Similarity	NPC471319
0.6261	Remote Similarity	NPC471320
0.6259	Remote Similarity	NPC178662
0.6259	Remote Similarity	NPC470884
0.6259	Remote Similarity	NPC98424
0.6259	Remote Similarity	NPC89489
0.6259	Remote Similarity	NPC470902
0.6259	Remote Similarity	NPC476133
0.6259	Remote Similarity	NPC92784
0.625	Remote Similarity	NPC287790
0.625	Remote Similarity	NPC258627
0.625	Remote Similarity	NPC3672
0.625	Remote Similarity	NPC329318
0.6239	Remote Similarity	NPC75496
0.6239	Remote Similarity	NPC123476
0.6239	Remote Similarity	NPC12730

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 NPC471447 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	81
0.1-0.2	471
0.2-0.3	1061
0.3-0.4	2492
0.4-0.5	3427
0.5-0.6	1454
0.6-0.7	159
0.7-0.8	5
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
0.7458	Intermediate Similarity	NPD3123	Discovery
0.7241	Intermediate Similarity	NPD2583	Phase 2
0.7193	Intermediate Similarity	NPD7130	Phase 3
0.7167	Intermediate Similarity	NPD4431	Clinical (unspecified phase)
0.7119	Intermediate Similarity	NPD480	Approved
0.708	Intermediate Similarity	NPD5103	Approved
0.7054	Intermediate Similarity	NPD6919	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD1344	Phase 2
0.6991	Remote Similarity	NPD813	Approved
0.6929	Remote Similarity	NPD2079	Discontinued
0.6905	Remote Similarity	NPD2584	Suspended
0.6818	Remote Similarity	NPD1080	Approved
0.6814	Remote Similarity	NPD787	Suspended
0.681	Remote Similarity	NPD1576	Approved
0.6797	Remote Similarity	NPD3125	Approved
0.6797	Remote Similarity	NPD2634	Clinical (unspecified phase)
0.6769	Remote Similarity	NPD3626	Phase 3
0.6754	Remote Similarity	NPD5630	Phase 1
0.675	Remote Similarity	NPD753	Approved
0.6726	Remote Similarity	NPD1724	Approved
0.6721	Remote Similarity	NPD2543	Discontinued
0.6696	Remote Similarity	NPD6588	Clinical (unspecified phase)
0.6696	Remote Similarity	NPD4803	Discontinued
0.6667	Remote Similarity	NPD6325	Discontinued
0.6641	Remote Similarity	NPD1781	Discontinued
0.6617	Remote Similarity	NPD6076	Approved
0.6617	Remote Similarity	NPD6075	Approved
0.661	Remote Similarity	NPD1064	Approved
0.661	Remote Similarity	NPD1065	Approved
0.6607	Remote Similarity	NPD4814	Discontinued
0.6594	Remote Similarity	NPD3434	Clinical (unspecified phase)
0.6585	Remote Similarity	NPD5631	Phase 3
0.6583	Remote Similarity	NPD4063	Clinical (unspecified phase)
0.6579	Remote Similarity	NPD466	Approved
0.6565	Remote Similarity	NPD3588	Discontinued
0.6555	Remote Similarity	NPD6406	Approved
0.6552	Remote Similarity	NPD855	Approved
0.6552	Remote Similarity	NPD2196	Discontinued
0.6552	Remote Similarity	NPD854	Approved
0.6538	Remote Similarity	NPD6792	Phase 3
0.6535	Remote Similarity	NPD1362	Clinical (unspecified phase)
0.6535	Remote Similarity	NPD9716	Approved
0.6532	Remote Similarity	NPD1323	Discontinued
0.6522	Remote Similarity	NPD742	Approved
0.6519	Remote Similarity	NPD8416	Discontinued
0.65	Remote Similarity	NPD4464	Clinical (unspecified phase)
0.6496	Remote Similarity	NPD3357	Discontinued
0.6496	Remote Similarity	NPD2244	Clinical (unspecified phase)
0.6491	Remote Similarity	NPD1099	Approved
0.6491	Remote Similarity	NPD1100	Approved
0.6489	Remote Similarity	NPD2585	Clinical (unspecified phase)
0.6466	Remote Similarity	NPD4207	Discontinued
0.6466	Remote Similarity	NPD7979	Clinical (unspecified phase)
0.6466	Remote Similarity	NPD1275	Phase 2
0.6463	Remote Similarity	NPD6395	Phase 2
0.6463	Remote Similarity	NPD6396	Clinical (unspecified phase)
0.6462	Remote Similarity	NPD5157	Phase 1
0.6462	Remote Similarity	NPD5159	Phase 2
0.6462	Remote Similarity	NPD5158	Clinical (unspecified phase)
0.646	Remote Similarity	NPD1081	Clinical (unspecified phase)
0.6454	Remote Similarity	NPD5481	Discontinued
0.6439	Remote Similarity	NPD5339	Clinical (unspecified phase)
0.6439	Remote Similarity	NPD3604	Clinical (unspecified phase)
0.6434	Remote Similarity	NPD3624	Phase 2
0.6434	Remote Similarity	NPD3282	Phase 1
0.6434	Remote Similarity	NPD4478	Clinical (unspecified phase)
0.6434	Remote Similarity	NPD3283	Phase 3
0.6429	Remote Similarity	NPD6690	Approved
0.6429	Remote Similarity	NPD5991	Approved
0.6429	Remote Similarity	NPD5990	Approved
0.6423	Remote Similarity	NPD6817	Clinical (unspecified phase)
0.6419	Remote Similarity	NPD7011	Discontinued
0.6417	Remote Similarity	NPD3420	Clinical (unspecified phase)
0.6412	Remote Similarity	NPD2031	Discontinued
0.641	Remote Similarity	NPD2171	Approved
0.641	Remote Similarity	NPD1417	Approved
0.641	Remote Similarity	NPD2648	Phase 3
0.641	Remote Similarity	NPD1419	Approved
0.641	Remote Similarity	NPD2193	Phase 2
0.6408	Remote Similarity	NPD603	Approved
0.6408	Remote Similarity	NPD4147	Approved
0.6408	Remote Similarity	NPD4144	Approved
0.6404	Remote Similarity	NPD157	Clinical (unspecified phase)
0.6404	Remote Similarity	NPD2507	Clinical (unspecified phase)
0.64	Remote Similarity	NPD1025	Discontinued
0.6397	Remote Similarity	NPD5272	Discontinued
0.6387	Remote Similarity	NPD1766	Approved
0.6387	Remote Similarity	NPD1761	Approved
0.6387	Remote Similarity	NPD1767	Approved
0.6387	Remote Similarity	NPD1765	Approved
0.6387	Remote Similarity	NPD2197	Approved
0.6387	Remote Similarity	NPD2192	Approved
0.6387	Remote Similarity	NPD1763	Approved
0.6381	Remote Similarity	NPD5371	Approved
0.6381	Remote Similarity	NPD5372	Approved
0.6378	Remote Similarity	NPD6345	Approved
0.6378	Remote Similarity	NPD6343	Approved
0.6377	Remote Similarity	NPD4214	Discontinued
0.6371	Remote Similarity	NPD3598	Phase 3
0.6371	Remote Similarity	NPD23	Approved
0.637	Remote Similarity	NPD3632	Clinical (unspecified phase)
0.637	Remote Similarity	NPD1329	Clinical (unspecified phase)
0.637	Remote Similarity	NPD2846	Clinical (unspecified phase)
0.637	Remote Similarity	NPD1330	Phase 2
0.6364	Remote Similarity	NPD2679	Approved
0.6364	Remote Similarity	NPD3029	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD6609	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD2678	Approved
0.6357	Remote Similarity	NPD1079	Discontinued
0.6356	Remote Similarity	NPD1396	Approved
0.6355	Remote Similarity	NPD3971	Phase 1
0.635	Remote Similarity	NPD7113	Clinical (unspecified phase)
0.6345	Remote Similarity	NPD3821	Clinical (unspecified phase)
0.6345	Remote Similarity	NPD3822	Approved
0.6345	Remote Similarity	NPD3820	Approved
0.6343	Remote Similarity	NPD4125	Approved
0.6331	Remote Similarity	NPD6655	Clinical (unspecified phase)
0.6331	Remote Similarity	NPD4158	Clinical (unspecified phase)
0.6324	Remote Similarity	NPD941	Approved
0.632	Remote Similarity	NPD851	Approved
0.632	Remote Similarity	NPD853	Approved
0.6316	Remote Similarity	NPD6259	Discontinued
0.6316	Remote Similarity	NPD3608	Clinical (unspecified phase)
0.6311	Remote Similarity	NPD3581	Discontinued
0.6308	Remote Similarity	NPD1948	Approved
0.6308	Remote Similarity	NPD7462	Clinical (unspecified phase)
0.6306	Remote Similarity	NPD689	Discontinued
0.6304	Remote Similarity	NPD4782	Clinical (unspecified phase)
0.6304	Remote Similarity	NPD8172	Phase 2
0.6304	Remote Similarity	NPD8173	Phase 2
0.6299	Remote Similarity	NPD7522	Discontinued
0.6296	Remote Similarity	NPD5178	Approved
0.629	Remote Similarity	NPD3066	Phase 2
0.629	Remote Similarity	NPD4165	Phase 2
0.6288	Remote Similarity	NPD6330	Clinical (unspecified phase)
0.6283	Remote Similarity	NPD1814	Approved
0.6283	Remote Similarity	NPD1812	Approved
0.6281	Remote Similarity	NPD2243	Clinical (unspecified phase)
0.6281	Remote Similarity	NPD6038	Clinical (unspecified phase)
0.6281	Remote Similarity	NPD4095	Clinical (unspecified phase)
0.6273	Remote Similarity	NPD187	Approved
0.6271	Remote Similarity	NPD4818	Approved
0.6271	Remote Similarity	NPD4119	Approved
0.6271	Remote Similarity	NPD4817	Approved
0.6268	Remote Similarity	NPD6860	Clinical (unspecified phase)
0.6259	Remote Similarity	NPD4911	Discontinued
0.6259	Remote Similarity	NPD4077	Clinical (unspecified phase)
0.625	Remote Similarity	NPD999	Phase 2
0.625	Remote Similarity	NPD2078	Clinical (unspecified phase)
0.625	Remote Similarity	NPD1677	Discontinued
0.6241	Remote Similarity	NPD2093	Discontinued
0.6241	Remote Similarity	NPD7720	Phase 2
0.624	Remote Similarity	NPD5180	Approved
0.624	Remote Similarity	NPD5181	Approved
0.624	Remote Similarity	NPD5179	Approved
0.6239	Remote Similarity	NPD5734	Clinical (unspecified phase)
0.6239	Remote Similarity	NPD9712	Approved
0.6231	Remote Similarity	NPD1947	Approved
0.6228	Remote Similarity	NPD1066	Discontinued
0.6224	Remote Similarity	NPD6676	Phase 2
0.6224	Remote Similarity	NPD1968	Approved
0.6224	Remote Similarity	NPD1967	Approved
0.6222	Remote Similarity	NPD6729	Phase 2
0.6218	Remote Similarity	NPD3682	Approved
0.6218	Remote Similarity	NPD3680	Approved
0.6218	Remote Similarity	NPD3681	Approved
0.6218	Remote Similarity	NPD3683	Approved
0.6218	Remote Similarity	NPD6647	Phase 2
0.621	Remote Similarity	NPD4991	Discontinued
0.621	Remote Similarity	NPD2124	Approved
0.6207	Remote Similarity	NPD2013	Approved
0.6207	Remote Similarity	NPD2014	Approved
0.6207	Remote Similarity	NPD528	Clinical (unspecified phase)
0.6207	Remote Similarity	NPD7441	Clinical (unspecified phase)
0.6207	Remote Similarity	NPD2016	Approved
0.6202	Remote Similarity	NPD1217	Clinical (unspecified phase)
0.6202	Remote Similarity	NPD2212	Approved
0.6202	Remote Similarity	NPD2210	Approved
0.6197	Remote Similarity	NPD3513	Phase 3
0.6197	Remote Similarity	NPD6681	Discovery
0.619	Remote Similarity	NPD3551	Approved
0.6186	Remote Similarity	NPD4760	Clinical (unspecified phase)
0.6176	Remote Similarity	NPD2049	Clinical (unspecified phase)
0.6176	Remote Similarity	NPD2045	Approved
0.6176	Remote Similarity	NPD2043	Approved
0.6176	Remote Similarity	NPD2046	Approved
0.6176	Remote Similarity	NPD21	Approved
0.6176	Remote Similarity	NPD2044	Approved
0.6176	Remote Similarity	NPD2050	Clinical (unspecified phase)
0.6176	Remote Similarity	NPD4497	Clinical (unspecified phase)
0.6176	Remote Similarity	NPD2051	Approved
0.6176	Remote Similarity	NPD2048	Approved
0.6176	Remote Similarity	NPD2047	Approved
0.6174	Remote Similarity	NPD2891	Approved
0.6174	Remote Similarity	NPD4094	Approved
0.6172	Remote Similarity	NPD997	Clinical (unspecified phase)
0.617	Remote Similarity	NPD6897	Clinical (unspecified phase)
0.6168	Remote Similarity	NPD4027	Approved
0.6168	Remote Similarity	NPD4026	Approved
0.6167	Remote Similarity	NPD2577	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