NPASS Compound

Structure

NPC78530 OpenBabel07101719512D 29 30 0 0 0 0 0 0 0 0999 V2000 -9.5263 5.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 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 -6.0622 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.6603 3.0000 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 -2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 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 4.0000 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 -0.8660 1.5000 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 -1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 4.5000 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 -0.0000 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.6603 4.0000 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 0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 5.5000 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -0.5000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 1.5000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.5263 4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 28 1 0 0 0 0 2 8 1 0 0 0 0 2 10 1 0 0 0 0 3 5 2 0 0 0 0 3 14 1 0 0 0 0 4 6 2 0 0 0 0 4 14 1 0 0 0 0 5 19 1 0 0 0 0 6 20 1 0 0 0 0 7 9 1 0 0 0 0 7 15 1 0 0 0 0 8 25 1 0 0 0 0 9 26 1 0 0 0 0 10 29 1 0 0 0 0 11 14 2 0 0 0 0 11 16 1 0 0 0 0 12 15 2 0 0 0 0 12 17 1 0 0 0 0 13 15 1 0 0 0 0 13 18 2 0 0 0 0 16 19 2 0 0 0 0 16 22 1 0 0 0 0 17 21 2 0 0 0 0 17 23 1 0 0 0 0 18 21 1 0 0 0 0 18 24 1 0 0 0 0 19 28 1 0 0 0 0 20 26 2 3 0 0 0 20 27 1 0 0 0 0 21 29 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	587.93
Volume:	439.783
LogP:	4.487
LogD:	3.455
LogS:	-5.497
# Rotatable Bonds:	11
TPSA:	73.58
# H-Bond Aceptor:	5
# H-Bond Donor:	3
# Rings:	2
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.299
Synthetic Accessibility Score:	2.467
Fsp3:	0.286
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.243
MDCK Permeability:	1.4486072359432e-05
Pgp-inhibitor:	0.999
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.024
20% Bioavailability (F20%):	0.001
30% Bioavailability (F30%):	0.002

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.977
Plasma Protein Binding (PPB):	97.4382095336914%
Volume Distribution (VD):	1.054
Pgp-substrate:	2.3090767860412598%

ADMET: Metabolism

CYP1A2-inhibitor:	0.916
CYP1A2-substrate:	0.384
CYP2C19-inhibitor:	0.96
CYP2C19-substrate:	0.235
CYP2C9-inhibitor:	0.876
CYP2C9-substrate:	0.927
CYP2D6-inhibitor:	0.859
CYP2D6-substrate:	0.912
CYP3A4-inhibitor:	0.925
CYP3A4-substrate:	0.207

ADMET: Excretion

Clearance (CL):	0.794
Half-life (T1/2):	0.17

ADMET: Toxicity

hERG Blockers:	0.982
Human Hepatotoxicity (H-HT):	0.275
Drug-inuced Liver Injury (DILI):	0.53
AMES Toxicity:	0.016
Rat Oral Acute Toxicity:	0.147
Maximum Recommended Daily Dose:	0.903
Skin Sensitization:	0.68
Carcinogencity:	0.154
Eye Corrosion:	0.003
Eye Irritation:	0.012
Respiratory Toxicity:	0.835

Download Data

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

Natural Product: NPC78530

Natural Product ID:	NPC78530
*Common Name:**	Aplysamine 6
IUPAC Name:	(E)-N-[2-[4-(3-aminopropoxy)-3,5-dibromophenyl]ethyl]-3-(3-bromo-4-methoxyphenyl)prop-2-enamide
Synonyms:
Standard InCHIKey:	MZLANVULBFGHHK-GQCTYLIASA-N
Standard InCHI:	InChI=1S/C21H23Br3N2O3/c1-28-19-5-3-14(11-16(19)22)4-6-20(27)26-9-7-15-12-17(23)21(18(24)13-15)29-10-2-8-25/h3-6,11-13H,2,7-10,25H2,1H3,(H,26,27)/b6-4+
SMILES:	NCCCOc1c(Br)cc(cc1Br)CCN=C(/C=C/c1ccc(c(c1)Br)OC)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL482878
PubChem CID:	24899922
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
NPO32681	pseudoceratina sp.	Species	Pseudoceratinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[18393464]
NPO32681	pseudoceratina sp.	Species	Pseudoceratinidae	Eukaryota	n.a.	Okinawan	n.a.	PMID[20584605]
NPO32681	pseudoceratina sp.	Species	Pseudoceratinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[24964362]

☑ 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

Activity Type	# Activity
SINGLE PROTEIN	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT27452	SINGLE PROTEIN	Isoprenylcysteine carboxyl methyltransferase	Homo sapiens	IC50	=	14000.0	nM	PMID[545493]

☑ 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 NPC78530 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	216
0.1-0.2	2839
0.2-0.3	12639
0.3-0.4	5637
0.4-0.5	11760
0.5-0.6	8528
0.6-0.7	941
0.7-0.8	109
0.8-0.85	13
0.85-0.9	9
0.9-0.95	4
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.95	High Similarity	NPC76412
0.9281	High Similarity	NPC135349
0.9231	High Similarity	NPC47672
0.9041	High Similarity	NPC233926
0.9041	High Similarity	NPC156311
0.8777	High Similarity	NPC470471
0.8767	High Similarity	NPC258222
0.8741	High Similarity	NPC470472
0.8731	High Similarity	NPC272463
0.8652	High Similarity	NPC470470
0.8521	High Similarity	NPC474673
0.8472	Intermediate Similarity	NPC474128
0.8394	Intermediate Similarity	NPC110131
0.8358	Intermediate Similarity	NPC263835
0.8267	Intermediate Similarity	NPC109968
0.8264	Intermediate Similarity	NPC213471
0.8188	Intermediate Similarity	NPC296085
0.8082	Intermediate Similarity	NPC128877
0.8067	Intermediate Similarity	NPC71629
0.8056	Intermediate Similarity	NPC303993
0.8041	Intermediate Similarity	NPC308571
0.7883	Intermediate Similarity	NPC256369
0.7857	Intermediate Similarity	NPC469711
0.7847	Intermediate Similarity	NPC475735
0.7847	Intermediate Similarity	NPC473724
0.7778	Intermediate Similarity	NPC99280
0.7778	Intermediate Similarity	NPC474091
0.7754	Intermediate Similarity	NPC43275
0.773	Intermediate Similarity	NPC211218
0.7676	Intermediate Similarity	NPC62101
0.7676	Intermediate Similarity	NPC95733
0.7647	Intermediate Similarity	NPC115803
0.7591	Intermediate Similarity	NPC303370
0.7574	Intermediate Similarity	NPC59387
0.7561	Intermediate Similarity	NPC477255
0.7556	Intermediate Similarity	NPC166837
0.75	Intermediate Similarity	NPC29477
0.7485	Intermediate Similarity	NPC77435
0.7485	Intermediate Similarity	NPC469979
0.7485	Intermediate Similarity	NPC259071
0.7483	Intermediate Similarity	NPC11449
0.7483	Intermediate Similarity	NPC328267
0.7456	Intermediate Similarity	NPC475396
0.7448	Intermediate Similarity	NPC301713
0.7445	Intermediate Similarity	NPC26524
0.7442	Intermediate Similarity	NPC473892
0.7442	Intermediate Similarity	NPC475658
0.744	Intermediate Similarity	NPC298981
0.744	Intermediate Similarity	NPC207819
0.744	Intermediate Similarity	NPC110454
0.744	Intermediate Similarity	NPC473462
0.744	Intermediate Similarity	NPC126128
0.7432	Intermediate Similarity	NPC471953
0.7397	Intermediate Similarity	NPC251571
0.7394	Intermediate Similarity	NPC318357
0.7381	Intermediate Similarity	NPC226001
0.7368	Intermediate Similarity	NPC477254
0.7351	Intermediate Similarity	NPC309667
0.7347	Intermediate Similarity	NPC155838
0.733	Intermediate Similarity	NPC227953
0.7321	Intermediate Similarity	NPC225130
0.731	Intermediate Similarity	NPC214188
0.731	Intermediate Similarity	NPC74618
0.731	Intermediate Similarity	NPC301941
0.7299	Intermediate Similarity	NPC141405
0.7299	Intermediate Similarity	NPC82741
0.7299	Intermediate Similarity	NPC473409
0.7297	Intermediate Similarity	NPC52029
0.7297	Intermediate Similarity	NPC35961
0.7297	Intermediate Similarity	NPC195749
0.7283	Intermediate Similarity	NPC121571
0.7283	Intermediate Similarity	NPC8093
0.7279	Intermediate Similarity	NPC78061
0.7279	Intermediate Similarity	NPC159987
0.7279	Intermediate Similarity	NPC122359
0.7241	Intermediate Similarity	NPC471591
0.7239	Intermediate Similarity	NPC42383
0.7237	Intermediate Similarity	NPC470249
0.7219	Intermediate Similarity	NPC71888
0.7219	Intermediate Similarity	NPC120114
0.7208	Intermediate Similarity	NPC212850
0.7208	Intermediate Similarity	NPC189724
0.7208	Intermediate Similarity	NPC83289
0.7206	Intermediate Similarity	NPC24101
0.7206	Intermediate Similarity	NPC96224
0.72	Intermediate Similarity	NPC307123
0.72	Intermediate Similarity	NPC97870
0.72	Intermediate Similarity	NPC214869
0.72	Intermediate Similarity	NPC247018
0.7193	Intermediate Similarity	NPC290534
0.7191	Intermediate Similarity	NPC202866
0.7184	Intermediate Similarity	NPC49172
0.7181	Intermediate Similarity	NPC135173
0.7172	Intermediate Similarity	NPC471314
0.7172	Intermediate Similarity	NPC471315
0.7171	Intermediate Similarity	NPC235633
0.7162	Intermediate Similarity	NPC186898
0.7153	Intermediate Similarity	NPC83279
0.7143	Intermediate Similarity	NPC144823
0.7143	Intermediate Similarity	NPC174607
0.7135	Intermediate Similarity	NPC474678
0.7135	Intermediate Similarity	NPC471338
0.7133	Intermediate Similarity	NPC114102
0.7102	Intermediate Similarity	NPC147847
0.7101	Intermediate Similarity	NPC473358
0.7095	Intermediate Similarity	NPC475843
0.7095	Intermediate Similarity	NPC469721
0.7086	Intermediate Similarity	NPC474753
0.7086	Intermediate Similarity	NPC470392
0.7083	Intermediate Similarity	NPC321133
0.708	Intermediate Similarity	NPC97811
0.7078	Intermediate Similarity	NPC312770
0.7078	Intermediate Similarity	NPC160607
0.7078	Intermediate Similarity	NPC204848
0.7078	Intermediate Similarity	NPC41473
0.7078	Intermediate Similarity	NPC14600
0.7078	Intermediate Similarity	NPC197045
0.7075	Intermediate Similarity	NPC213414
0.7075	Intermediate Similarity	NPC236265
0.7067	Intermediate Similarity	NPC474087
0.7047	Intermediate Similarity	NPC153990
0.7044	Intermediate Similarity	NPC132771
0.7044	Intermediate Similarity	NPC245974
0.7042	Intermediate Similarity	NPC258992
0.7039	Intermediate Similarity	NPC163810
0.7035	Intermediate Similarity	NPC475615
0.7032	Intermediate Similarity	NPC299583
0.7027	Intermediate Similarity	NPC320242
0.7025	Intermediate Similarity	NPC247298
0.7017	Intermediate Similarity	NPC469731
0.7013	Intermediate Similarity	NPC475132
0.7013	Intermediate Similarity	NPC470248
0.7013	Intermediate Similarity	NPC474587
0.7007	Intermediate Similarity	NPC142297
0.7	Intermediate Similarity	NPC277857
0.7	Intermediate Similarity	NPC115144
0.6995	Remote Similarity	NPC471337
0.6993	Remote Similarity	NPC323948
0.6981	Remote Similarity	NPC313414
0.6968	Remote Similarity	NPC475293
0.6966	Remote Similarity	NPC289330
0.6966	Remote Similarity	NPC17388
0.6966	Remote Similarity	NPC471308
0.6966	Remote Similarity	NPC41801
0.6966	Remote Similarity	NPC53596
0.6966	Remote Similarity	NPC160120
0.6963	Remote Similarity	NPC192596
0.6962	Remote Similarity	NPC63628
0.6962	Remote Similarity	NPC178466
0.6957	Remote Similarity	NPC471495
0.6957	Remote Similarity	NPC471032
0.6957	Remote Similarity	NPC470935
0.6948	Remote Similarity	NPC237227
0.6939	Remote Similarity	NPC296202
0.6939	Remote Similarity	NPC116562
0.6934	Remote Similarity	NPC231705
0.6928	Remote Similarity	NPC169766
0.6927	Remote Similarity	NPC248822
0.6923	Remote Similarity	NPC296898
0.6914	Remote Similarity	NPC139699
0.6914	Remote Similarity	NPC114659
0.691	Remote Similarity	NPC470951
0.6906	Remote Similarity	NPC54543
0.6902	Remote Similarity	NPC123140
0.6897	Remote Similarity	NPC283760
0.6892	Remote Similarity	NPC105999
0.6889	Remote Similarity	NPC51633
0.6884	Remote Similarity	NPC186469
0.6879	Remote Similarity	NPC143450
0.6871	Remote Similarity	NPC7830
0.6871	Remote Similarity	NPC475432
0.6867	Remote Similarity	NPC218323
0.6863	Remote Similarity	NPC274732
0.6863	Remote Similarity	NPC158078
0.6861	Remote Similarity	NPC470393
0.6842	Remote Similarity	NPC470706
0.6842	Remote Similarity	NPC478071
0.6838	Remote Similarity	NPC178902
0.6835	Remote Similarity	NPC146530
0.6835	Remote Similarity	NPC153690
0.6829	Remote Similarity	NPC235033
0.6829	Remote Similarity	NPC73132
0.6829	Remote Similarity	NPC471235
0.6821	Remote Similarity	NPC202776
0.6818	Remote Similarity	NPC152205
0.6818	Remote Similarity	NPC475283
0.6815	Remote Similarity	NPC40321
0.6812	Remote Similarity	NPC113457
0.6806	Remote Similarity	NPC82963
0.68	Remote Similarity	NPC136112
0.68	Remote Similarity	NPC141739
0.6792	Remote Similarity	NPC222039
0.6792	Remote Similarity	NPC100478
0.6792	Remote Similarity	NPC470247
0.6788	Remote Similarity	NPC38079
0.6788	Remote Similarity	NPC108875
0.6786	Remote Similarity	NPC258056
0.6786	Remote Similarity	NPC22014
0.6779	Remote Similarity	NPC13020
0.6779	Remote Similarity	NPC140359

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 NPC78530 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	147
0.1-0.2	800
0.2-0.3	1189
0.3-0.4	2277
0.4-0.5	2861
0.5-0.6	1406
0.6-0.7	441
0.7-0.8	29
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
0.7483	Intermediate Similarity	NPD2429	Approved
0.7483	Intermediate Similarity	NPD2428	Approved
0.7447	Intermediate Similarity	NPD2556	Approved
0.7447	Intermediate Similarity	NPD2554	Approved
0.7413	Intermediate Similarity	NPD2235	Phase 2
0.7413	Intermediate Similarity	NPD2231	Phase 2
0.74	Intermediate Similarity	NPD3054	Approved
0.74	Intermediate Similarity	NPD3052	Approved
0.7397	Intermediate Similarity	NPD4993	Discontinued
0.7365	Intermediate Similarity	NPD3056	Clinical (unspecified phase)
0.7338	Intermediate Similarity	NPD2458	Approved
0.7338	Intermediate Similarity	NPD2459	Approved
0.7338	Intermediate Similarity	NPD2460	Phase 3
0.7297	Intermediate Similarity	NPD5163	Phase 2
0.7273	Intermediate Similarity	NPD7153	Discontinued
0.7255	Intermediate Similarity	NPD3175	Clinical (unspecified phase)
0.7254	Intermediate Similarity	NPD3049	Approved
0.7241	Intermediate Similarity	NPD1669	Approved
0.7241	Intermediate Similarity	NPD4129	Approved
0.72	Intermediate Similarity	NPD1423	Approved
0.72	Intermediate Similarity	NPD7477	Discontinued
0.717	Intermediate Similarity	NPD5261	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD1770	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD3568	Approved
0.7143	Intermediate Similarity	NPD3567	Approved
0.7123	Intermediate Similarity	NPD6582	Phase 2
0.7123	Intermediate Similarity	NPD6583	Phase 3
0.7123	Intermediate Similarity	NPD3676	Clinical (unspecified phase)
0.7122	Intermediate Similarity	NPD821	Approved
0.7115	Intermediate Similarity	NPD4162	Approved
0.7107	Intermediate Similarity	NPD2874	Phase 2
0.7107	Intermediate Similarity	NPD3985	Discontinued
0.7083	Intermediate Similarity	NPD2667	Approved
0.7083	Intermediate Similarity	NPD2668	Approved
0.7078	Intermediate Similarity	NPD6380	Phase 1
0.7067	Intermediate Similarity	NPD6179	Discontinued
0.7063	Intermediate Similarity	NPD2184	Approved
0.7063	Intermediate Similarity	NPD2183	Approved
0.7042	Intermediate Similarity	NPD3596	Phase 2
0.7039	Intermediate Similarity	NPD5837	Clinical (unspecified phase)
0.7032	Intermediate Similarity	NPD3156	Discontinued
0.7027	Intermediate Similarity	NPD1817	Approved
0.7027	Intermediate Similarity	NPD1820	Approved
0.7027	Intermediate Similarity	NPD1818	Approved
0.7027	Intermediate Similarity	NPD1819	Approved
0.7006	Intermediate Similarity	NPD2976	Clinical (unspecified phase)
0.698	Remote Similarity	NPD6584	Phase 3
0.6974	Remote Similarity	NPD840	Approved
0.6974	Remote Similarity	NPD839	Approved
0.6974	Remote Similarity	NPD3532	Approved
0.6974	Remote Similarity	NPD3531	Approved
0.6974	Remote Similarity	NPD3530	Approved
0.6968	Remote Similarity	NPD7425	Clinical (unspecified phase)
0.6962	Remote Similarity	NPD6331	Phase 2
0.6957	Remote Similarity	NPD52	Approved
0.6957	Remote Similarity	NPD7527	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD7526	Approved
0.6954	Remote Similarity	NPD3164	Approved
0.6954	Remote Similarity	NPD3166	Approved
0.6954	Remote Similarity	NPD3165	Approved
0.6954	Remote Similarity	NPD9718	Approved
0.6954	Remote Similarity	NPD3167	Approved
0.6944	Remote Similarity	NPD6580	Approved
0.6944	Remote Similarity	NPD6581	Approved
0.6943	Remote Similarity	NPD7596	Clinical (unspecified phase)
0.6937	Remote Similarity	NPD6087	Phase 1
0.6928	Remote Similarity	NPD3597	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD7131	Phase 3
0.6914	Remote Similarity	NPD5586	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD6830	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD2595	Approved
0.6897	Remote Similarity	NPD2594	Approved
0.6894	Remote Similarity	NPD3536	Discontinued
0.6894	Remote Similarity	NPD4123	Phase 3
0.6892	Remote Similarity	NPD3685	Discontinued
0.6887	Remote Similarity	NPD5752	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD2614	Approved
0.6867	Remote Similarity	NPD7451	Discontinued
0.6855	Remote Similarity	NPD6658	Clinical (unspecified phase)
0.6853	Remote Similarity	NPD2557	Approved
0.6852	Remote Similarity	NPD4186	Clinical (unspecified phase)
0.6848	Remote Similarity	NPD6072	Discontinued
0.6842	Remote Similarity	NPD3179	Approved
0.6842	Remote Similarity	NPD3180	Approved
0.6839	Remote Similarity	NPD2157	Approved
0.6835	Remote Similarity	NPD2030	Discontinued
0.6828	Remote Similarity	NPD2486	Discontinued
0.6821	Remote Similarity	NPD1712	Approved
0.6821	Remote Similarity	NPD5266	Clinical (unspecified phase)
0.6815	Remote Similarity	NPD2161	Phase 2
0.68	Remote Similarity	NPD1794	Approved
0.68	Remote Similarity	NPD4098	Discontinued
0.68	Remote Similarity	NPD1232	Clinical (unspecified phase)
0.6797	Remote Similarity	NPD3374	Clinical (unspecified phase)
0.6792	Remote Similarity	NPD44	Approved
0.6792	Remote Similarity	NPD6364	Approved
0.6792	Remote Similarity	NPD3060	Approved
0.679	Remote Similarity	NPD6419	Discontinued
0.679	Remote Similarity	NPD7020	Approved
0.679	Remote Similarity	NPD7019	Approved
0.6783	Remote Similarity	NPD595	Approved
0.6783	Remote Similarity	NPD593	Approved
0.6781	Remote Similarity	NPD6382	Discontinued
0.6772	Remote Similarity	NPD3656	Approved
0.6755	Remote Similarity	NPD558	Phase 2
0.6755	Remote Similarity	NPD3690	Phase 2
0.6755	Remote Similarity	NPD3691	Phase 2
0.6753	Remote Similarity	NPD2245	Discovery
0.6753	Remote Similarity	NPD5745	Approved
0.6753	Remote Similarity	NPD2674	Phase 3
0.6753	Remote Similarity	NPD3058	Clinical (unspecified phase)
0.6752	Remote Similarity	NPD2155	Approved
0.6752	Remote Similarity	NPD2154	Approved
0.6752	Remote Similarity	NPD4108	Discontinued
0.6752	Remote Similarity	NPD3693	Clinical (unspecified phase)
0.6752	Remote Similarity	NPD2156	Approved
0.6733	Remote Similarity	NPD7258	Clinical (unspecified phase)
0.6727	Remote Similarity	NPD6523	Clinical (unspecified phase)
0.6723	Remote Similarity	NPD2802	Phase 3
0.6714	Remote Similarity	NPD2684	Approved
0.6711	Remote Similarity	NPD2232	Approved
0.6711	Remote Similarity	NPD2562	Approved
0.6711	Remote Similarity	NPD2230	Approved
0.6711	Remote Similarity	NPD2233	Approved
0.6711	Remote Similarity	NPD2561	Approved
0.6711	Remote Similarity	NPD2407	Clinical (unspecified phase)
0.6709	Remote Similarity	NPD1725	Approved
0.6708	Remote Similarity	NPD3692	Discontinued
0.6708	Remote Similarity	NPD5160	Discontinued
0.6689	Remote Similarity	NPD3294	Phase 2
0.6688	Remote Similarity	NPD3145	Approved
0.6688	Remote Similarity	NPD3144	Approved
0.6687	Remote Similarity	NPD5061	Approved
0.6687	Remote Similarity	NPD2504	Approved
0.6687	Remote Similarity	NPD5062	Approved
0.6687	Remote Similarity	NPD4675	Approved
0.6687	Remote Similarity	NPD4678	Approved
0.6687	Remote Similarity	NPD2505	Approved
0.6687	Remote Similarity	NPD5348	Clinical (unspecified phase)
0.6687	Remote Similarity	NPD1771	Clinical (unspecified phase)
0.6684	Remote Similarity	NPD3336	Discovery
0.6667	Remote Similarity	NPD6543	Approved
0.6667	Remote Similarity	NPD5865	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6540	Phase 3
0.6667	Remote Similarity	NPD3445	Approved
0.6667	Remote Similarity	NPD6542	Approved
0.6667	Remote Similarity	NPD3443	Approved
0.6667	Remote Similarity	NPD5267	Discontinued
0.6667	Remote Similarity	NPD1411	Approved
0.6667	Remote Similarity	NPD3444	Approved
0.6667	Remote Similarity	NPD6539	Approved
0.6647	Remote Similarity	NPD2541	Clinical (unspecified phase)
0.6647	Remote Similarity	NPD8031	Discontinued
0.6646	Remote Similarity	NPD1169	Approved
0.6645	Remote Similarity	NPD7018	Phase 2
0.6645	Remote Similarity	NPD3163	Approved
0.6645	Remote Similarity	NPD3162	Approved
0.6645	Remote Similarity	NPD1726	Clinical (unspecified phase)
0.6625	Remote Similarity	NPD4598	Approved
0.6625	Remote Similarity	NPD4597	Approved
0.6625	Remote Similarity	NPD4149	Clinical (unspecified phase)
0.6624	Remote Similarity	NPD1772	Clinical (unspecified phase)
0.6623	Remote Similarity	NPD3136	Phase 2
0.6623	Remote Similarity	NPD1024	Discontinued
0.6623	Remote Similarity	NPD5746	Approved
0.6623	Remote Similarity	NPD6541	Approved
0.6623	Remote Similarity	NPD6538	Approved
0.6607	Remote Similarity	NPD4018	Clinical (unspecified phase)
0.6607	Remote Similarity	NPD7945	Clinical (unspecified phase)
0.6604	Remote Similarity	NPD2239	Approved
0.6604	Remote Similarity	NPD1538	Phase 1
0.6604	Remote Similarity	NPD1519	Approved
0.6604	Remote Similarity	NPD1537	Approved
0.6604	Remote Similarity	NPD2240	Approved
0.6601	Remote Similarity	NPD2250	Discontinued
0.6597	Remote Similarity	NPD594	Approved
0.6597	Remote Similarity	NPD592	Approved
0.6588	Remote Similarity	NPD7773	Phase 2
0.6587	Remote Similarity	NPD6502	Phase 2
0.6587	Remote Similarity	NPD1009	Approved
0.6587	Remote Similarity	NPD3679	Phase 2
0.6582	Remote Similarity	NPD3553	Approved
0.6582	Remote Similarity	NPD3552	Approved
0.6582	Remote Similarity	NPD3555	Approved
0.6582	Remote Similarity	NPD1536	Approved
0.6582	Remote Similarity	NPD3554	Approved
0.6581	Remote Similarity	NPD6812	Clinical (unspecified phase)
0.6581	Remote Similarity	NPD1039	Discontinued
0.6577	Remote Similarity	NPD3421	Phase 3
0.6571	Remote Similarity	NPD968	Approved
0.6568	Remote Similarity	NPD3465	Clinical (unspecified phase)
0.6568	Remote Similarity	NPD5773	Approved
0.6568	Remote Similarity	NPD5772	Approved
0.6558	Remote Similarity	NPD600	Approved
0.6558	Remote Similarity	NPD596	Approved
0.6549	Remote Similarity	NPD9380	Clinical (unspecified phase)
0.6547	Remote Similarity	NPD9608	Approved
0.6547	Remote Similarity	NPD9610	Approved
0.6541	Remote Similarity	NPD2661	Clinical (unspecified phase)
0.6541	Remote Similarity	NPD3846	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