NPASS Compound

Structure

NPC121571 OpenBabel07101718242D 34 36 0 0 1 0 0 0 0 0999 V2000 -4.3577 -1.6441 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6808 -2.7024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.8769 -4.7024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.8769 -5.7024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8147 -3.2024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5468 -3.2024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.0109 -3.2024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.1449 -4.7024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8373 -1.8074 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0185 0.1040 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.0109 -4.2024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.1449 -2.7024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2788 -4.2024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7837 -2.1306 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7309 -0.5977 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 -2.6264 -1.5923 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2788 -3.2024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1691 -1.6092 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.9487 -1.7024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5000 -0.8660 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 7.1449 -1.7024 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 5.4128 -4.7024 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 -1.9031 -3.1235 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 -3.6723 -0.2604 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 8.0109 -6.2024 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.9487 -2.7024 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.9781 -0.2079 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.0388 -2.5873 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.8147 -1.2024 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4771 -2.1180 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.4128 -2.7024 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0257 -0.0153 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 31 1 0 0 0 0 2 5 1 0 0 0 0 2 6 1 0 0 0 0 3 4 1 0 0 0 0 3 11 1 0 0 0 0 4 26 1 0 0 0 0 5 27 1 0 0 0 0 6 32 1 0 0 0 0 7 11 2 0 0 0 0 7 12 1 0 0 0 0 8 11 1 0 0 0 0 8 13 2 0 0 0 0 9 14 1 0 0 0 0 10 15 2 0 0 0 0 10 33 1 0 0 0 0 12 18 2 0 0 0 0 12 22 1 0 0 0 0 13 18 1 0 0 0 0 13 23 1 0 0 0 0 14 17 2 0 0 0 0 14 24 1 0 0 0 0 15 17 1 0 0 0 0 15 25 1 0 0 0 0 16 19 1 0 0 0 0 16 20 1 0 0 0 0 16 28 2 0 0 0 0 17 31 1 0 0 0 0 18 32 1 0 0 0 0 19 21 1 1 0 0 0 19 29 1 0 0 0 0 20 27 1 0 0 0 0 20 30 2 0 0 0 0 21 9 1 1 0 0 0 21 33 1 0 0 0 0 21 34 1 0 0 0 0 28 34 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	728.83
Volume:	490.514
LogP:	3.591
LogD:	2.65
LogS:	-2.932
# Rotatable Bonds:	10
TPSA:	121.14
# H-Bond Aceptor:	9
# H-Bond Donor:	4
# Rings:	3
# Heavy Atoms:	13

MedChem Properties

QED Drug-Likeness Score:	0.26
Synthetic Accessibility Score:	4.842
Fsp3:	0.429
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-5.303
MDCK Permeability:	1.6490999769303016e-05
Pgp-inhibitor:	0.945
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.509
20% Bioavailability (F20%):	0.945
30% Bioavailability (F30%):	0.993

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.447
Plasma Protein Binding (PPB):	95.6347885131836%
Volume Distribution (VD):	0.826
Pgp-substrate:	5.379601001739502%

ADMET: Metabolism

CYP1A2-inhibitor:	0.712
CYP1A2-substrate:	0.466
CYP2C19-inhibitor:	0.881
CYP2C19-substrate:	0.608
CYP2C9-inhibitor:	0.779
CYP2C9-substrate:	0.092
CYP2D6-inhibitor:	0.819
CYP2D6-substrate:	0.414
CYP3A4-inhibitor:	0.959
CYP3A4-substrate:	0.721

ADMET: Excretion

Clearance (CL):	1.318
Half-life (T1/2):	0.585

ADMET: Toxicity

hERG Blockers:	0.451
Human Hepatotoxicity (H-HT):	0.277
Drug-inuced Liver Injury (DILI):	0.541
AMES Toxicity:	0.396
Rat Oral Acute Toxicity:	0.561
Maximum Recommended Daily Dose:	0.92
Skin Sensitization:	0.352
Carcinogencity:	0.829
Eye Corrosion:	0.003
Eye Irritation:	0.005
Respiratory Toxicity:	0.659

Download Data

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

Natural Product: NPC121571

Natural Product ID:	NPC121571
*Common Name:**	Rel-(-)-Psammaplysine A
IUPAC Name:	(4R,5R)-N-[3-[4-(2-aminoethyl)-2,6-dibromophenoxy]propyl]-7,9-dibromo-4-hydroxy-8-methoxy-1,11-dioxa-2-azaspiro[4.6]undeca-2,7,9-triene-3-carboxamide
Synonyms:
Standard InCHIKey:	XVHHFAJHWSIGJS-TZIWHRDSSA-N
Standard InCHI:	InChI=1S/C21H23Br4N3O6/c1-31-17-14(24)9-21(33-10-15(17)25)19(29)16(28-34-21)20(30)27-5-2-6-32-18-12(22)7-11(3-4-26)8-13(18)23/h7-8,10,19,29H,2-6,9,26H2,1H3,(H,27,30)/t19-,21-/m1/s1
SMILES:	COC1=C(C[C@@]2([C@@H](C(=NO2)C(=O)NCCCOc2c(cc(CCN)cc2Br)Br)O)OC=C1Br)Br
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2419319
PubChem CID:	23252115
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002279] Benzene and substituted derivatives [CHEMONTID:0000186] Phenethylamines

*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
NPO32567	suberea sp.	Species	Aplysinellidae	Eukaryota	n.a.	n.a.	n.a.	PMID[11473442]
NPO32567	suberea sp.	Species	Aplysinellidae	Eukaryota	n.a.	n.a.	n.a.	PMID[23964644]

☑ 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
GI50	6

Activity Type	# Activity
Cell Line	6

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT370	Cell Line	NCI-H23	Homo sapiens	GI50	=	12400.0	nM	PMID[573314]
NPT2477	Cell Line	NUGC-3	Homo sapiens	GI50	=	3800.0	nM	PMID[573314]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	GI50	=	4300.0	nM	PMID[573314]
NPT369	Cell Line	ACHN	Homo sapiens	GI50	=	5100.0	nM	PMID[573314]
NPT306	Cell Line	PC-3	Homo sapiens	GI50	=	6900.0	nM	PMID[573314]
NPT148	Cell Line	HCT-15	Homo sapiens	GI50	=	3900.0	nM	PMID[573314]

☑ 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 NPC121571 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	221
0.1-0.2	1656
0.2-0.3	10232
0.3-0.4	8596
0.4-0.5	16836
0.5-0.6	4851
0.6-0.7	246
0.7-0.8	32
0.8-0.85	9
0.85-0.9	8
0.9-0.95	5
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC8093
0.9649	High Similarity	NPC474678
0.9649	High Similarity	NPC471338
0.9593	High Similarity	NPC475843
0.9333	High Similarity	NPC477255
0.9322	High Similarity	NPC123140
0.9322	High Similarity	NPC471337
0.9075	High Similarity	NPC77435
0.9075	High Similarity	NPC259071
0.907	High Similarity	NPC477254
0.8967	High Similarity	NPC471339
0.8967	High Similarity	NPC471336
0.8967	High Similarity	NPC470746
0.8771	High Similarity	NPC227953
0.8722	High Similarity	NPC202866
0.8639	High Similarity	NPC471335
0.8596	High Similarity	NPC174607
0.8547	High Similarity	NPC147847
0.7965	Intermediate Similarity	NPC156311
0.7688	Intermediate Similarity	NPC469711
0.7665	Intermediate Similarity	NPC128877
0.7633	Intermediate Similarity	NPC308571
0.763	Intermediate Similarity	NPC258222
0.7486	Intermediate Similarity	NPC47672
0.7471	Intermediate Similarity	NPC76412
0.7458	Intermediate Similarity	NPC233926
0.7429	Intermediate Similarity	NPC109968
0.7283	Intermediate Similarity	NPC78530
0.7257	Intermediate Similarity	NPC71629
0.7216	Intermediate Similarity	NPC248822
0.7193	Intermediate Similarity	NPC474673
0.7184	Intermediate Similarity	NPC135349
0.7181	Intermediate Similarity	NPC143450
0.7176	Intermediate Similarity	NPC470471
0.7159	Intermediate Similarity	NPC296085
0.7093	Intermediate Similarity	NPC470470
0.7091	Intermediate Similarity	NPC272463
0.7086	Intermediate Similarity	NPC470472
0.7069	Intermediate Similarity	NPC474128
0.7048	Intermediate Similarity	NPC110131
0.7026	Intermediate Similarity	NPC246591
0.7015	Intermediate Similarity	NPC473450
0.6901	Remote Similarity	NPC97870
0.6901	Remote Similarity	NPC247018
0.6901	Remote Similarity	NPC307123
0.685	Remote Similarity	NPC80514
0.6834	Remote Similarity	NPC102245
0.6825	Remote Similarity	NPC196091
0.6825	Remote Similarity	NPC473693
0.6825	Remote Similarity	NPC471568
0.6802	Remote Similarity	NPC473892
0.6802	Remote Similarity	NPC471591
0.6802	Remote Similarity	NPC475658
0.6802	Remote Similarity	NPC96275
0.6768	Remote Similarity	NPC473409
0.6768	Remote Similarity	NPC141405
0.6768	Remote Similarity	NPC82741
0.675	Remote Similarity	NPC64066
0.6736	Remote Similarity	NPC469979
0.6736	Remote Similarity	NPC226001
0.6718	Remote Similarity	NPC475396
0.6716	Remote Similarity	NPC65714
0.6701	Remote Similarity	NPC207819
0.6701	Remote Similarity	NPC110454
0.6701	Remote Similarity	NPC299806
0.6701	Remote Similarity	NPC298981
0.6701	Remote Similarity	NPC126128
0.6701	Remote Similarity	NPC473462
0.6685	Remote Similarity	NPC204546
0.6667	Remote Similarity	NPC49172
0.6667	Remote Similarity	NPC469479
0.665	Remote Similarity	NPC283207
0.6648	Remote Similarity	NPC20755
0.6618	Remote Similarity	NPC471592
0.661	Remote Similarity	NPC213471
0.6609	Remote Similarity	NPC474753
0.6601	Remote Similarity	NPC469721
0.6599	Remote Similarity	NPC74618
0.6599	Remote Similarity	NPC301941
0.6599	Remote Similarity	NPC214188
0.6598	Remote Similarity	NPC225130
0.6597	Remote Similarity	NPC186617
0.6595	Remote Similarity	NPC73132
0.6595	Remote Similarity	NPC471235
0.6595	Remote Similarity	NPC235033
0.659	Remote Similarity	NPC474087
0.6573	Remote Similarity	NPC40321
0.6571	Remote Similarity	NPC132308
0.6567	Remote Similarity	NPC230539
0.6557	Remote Similarity	NPC324081
0.6552	Remote Similarity	NPC473724
0.6552	Remote Similarity	NPC475735
0.655	Remote Similarity	NPC80337
0.655	Remote Similarity	NPC320242
0.6537	Remote Similarity	NPC469731
0.6514	Remote Similarity	NPC470392
0.6497	Remote Similarity	NPC290534
0.6497	Remote Similarity	NPC196708
0.6494	Remote Similarity	NPC474091
0.6477	Remote Similarity	NPC169766
0.6471	Remote Similarity	NPC116562
0.6468	Remote Similarity	NPC144823
0.645	Remote Similarity	NPC315542
0.6447	Remote Similarity	NPC475421
0.6444	Remote Similarity	NPC470709
0.6441	Remote Similarity	NPC303993
0.6436	Remote Similarity	NPC56635
0.6425	Remote Similarity	NPC197045
0.6418	Remote Similarity	NPC276120
0.6406	Remote Similarity	NPC67658
0.6406	Remote Similarity	NPC254700
0.6398	Remote Similarity	NPC14339
0.6389	Remote Similarity	NPC326027
0.6384	Remote Similarity	NPC163810
0.6373	Remote Similarity	NPC473502
0.6373	Remote Similarity	NPC209463
0.6372	Remote Similarity	NPC326333
0.6358	Remote Similarity	NPC136112
0.6358	Remote Similarity	NPC141739
0.6354	Remote Similarity	NPC472923
0.635	Remote Similarity	NPC470903
0.635	Remote Similarity	NPC167763
0.635	Remote Similarity	NPC470112
0.634	Remote Similarity	NPC469505
0.6324	Remote Similarity	NPC132771
0.6321	Remote Similarity	NPC81845
0.6316	Remote Similarity	NPC319320
0.6316	Remote Similarity	NPC287757
0.6316	Remote Similarity	NPC123859
0.6313	Remote Similarity	NPC235633
0.6287	Remote Similarity	NPC138083
0.6286	Remote Similarity	NPC242728
0.6281	Remote Similarity	NPC475615
0.6278	Remote Similarity	NPC470248
0.6278	Remote Similarity	NPC470249
0.6278	Remote Similarity	NPC106606
0.6276	Remote Similarity	NPC89831
0.6275	Remote Similarity	NPC470951
0.6271	Remote Similarity	NPC11449
0.6269	Remote Similarity	NPC158900
0.6269	Remote Similarity	NPC63931
0.6268	Remote Similarity	NPC477550
0.6268	Remote Similarity	NPC477552
0.6264	Remote Similarity	NPC81137
0.6243	Remote Similarity	NPC256689
0.6243	Remote Similarity	NPC470710
0.6243	Remote Similarity	NPC476268
0.6243	Remote Similarity	NPC123011
0.6233	Remote Similarity	NPC175150
0.6233	Remote Similarity	NPC243633
0.6228	Remote Similarity	NPC115803
0.6225	Remote Similarity	NPC94862
0.6218	Remote Similarity	NPC67080
0.6215	Remote Similarity	NPC99280
0.6215	Remote Similarity	NPC135173
0.6212	Remote Similarity	NPC164608
0.6212	Remote Similarity	NPC471165
0.6209	Remote Similarity	NPC477551
0.6195	Remote Similarity	NPC124626
0.6193	Remote Similarity	NPC280736
0.619	Remote Similarity	NPC323662
0.6188	Remote Similarity	NPC475283
0.6188	Remote Similarity	NPC309667
0.6188	Remote Similarity	NPC152205
0.6183	Remote Similarity	NPC313414
0.6179	Remote Similarity	NPC214368
0.6179	Remote Similarity	NPC156055
0.6175	Remote Similarity	NPC295795
0.6175	Remote Similarity	NPC251439
0.6173	Remote Similarity	NPC280022
0.6172	Remote Similarity	NPC149962
0.6169	Remote Similarity	NPC32064
0.6167	Remote Similarity	NPC470441
0.6146	Remote Similarity	NPC4910
0.6143	Remote Similarity	NPC144314
0.6136	Remote Similarity	NPC50562
0.6135	Remote Similarity	NPC473407
0.6135	Remote Similarity	NPC473378
0.6133	Remote Similarity	NPC6570
0.6131	Remote Similarity	NPC26108
0.6124	Remote Similarity	NPC195902
0.6114	Remote Similarity	NPC50548
0.6111	Remote Similarity	NPC243404
0.6105	Remote Similarity	NPC180207
0.6102	Remote Similarity	NPC159987
0.6102	Remote Similarity	NPC78061
0.6102	Remote Similarity	NPC122359
0.61	Remote Similarity	NPC50016
0.6099	Remote Similarity	NPC307682
0.6096	Remote Similarity	NPC9373
0.6096	Remote Similarity	NPC189908
0.6094	Remote Similarity	NPC212699
0.6094	Remote Similarity	NPC207675
0.6089	Remote Similarity	NPC275538
0.6089	Remote Similarity	NPC70485
0.6087	Remote Similarity	NPC83289
0.6087	Remote Similarity	NPC189724
0.6087	Remote Similarity	NPC174122
0.6087	Remote Similarity	NPC212850
0.6087	Remote Similarity	NPC64140

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 NPC121571 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	145
0.1-0.2	578
0.2-0.3	1457
0.3-0.4	2522
0.4-0.5	3085
0.5-0.6	1256
0.6-0.7	107
0.7-0.8	0
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
0.6954	Remote Similarity	NPD2240	Approved
0.6954	Remote Similarity	NPD2239	Approved
0.6901	Remote Similarity	NPD1423	Approved
0.6737	Remote Similarity	NPD7608	Discontinued
0.6718	Remote Similarity	NPD5192	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD3175	Clinical (unspecified phase)
0.6648	Remote Similarity	NPD2976	Clinical (unspecified phase)
0.6557	Remote Similarity	NPD3536	Discontinued
0.655	Remote Similarity	NPD1817	Approved
0.655	Remote Similarity	NPD1820	Approved
0.655	Remote Similarity	NPD1819	Approved
0.655	Remote Similarity	NPD1818	Approved
0.655	Remote Similarity	NPD1770	Clinical (unspecified phase)
0.6526	Remote Similarity	NPD8031	Discontinued
0.651	Remote Similarity	NPD7484	Phase 3
0.651	Remote Similarity	NPD7485	Phase 3
0.6502	Remote Similarity	NPD5165	Clinical (unspecified phase)
0.65	Remote Similarity	NPD3154	Approved
0.65	Remote Similarity	NPD3153	Approved
0.6494	Remote Similarity	NPD3180	Approved
0.6494	Remote Similarity	NPD3167	Approved
0.6494	Remote Similarity	NPD3166	Approved
0.6494	Remote Similarity	NPD9718	Approved
0.6494	Remote Similarity	NPD3179	Approved
0.6494	Remote Similarity	NPD3164	Approved
0.6494	Remote Similarity	NPD3165	Approved
0.6486	Remote Similarity	NPD7131	Phase 3
0.648	Remote Similarity	NPD1725	Approved
0.6467	Remote Similarity	NPD5348	Clinical (unspecified phase)
0.6436	Remote Similarity	NPD2541	Clinical (unspecified phase)
0.6436	Remote Similarity	NPD6677	Suspended
0.6406	Remote Similarity	NPD6315	Phase 2
0.64	Remote Similarity	NPD5163	Phase 2
0.6378	Remote Similarity	NPD3985	Discontinued
0.6378	Remote Similarity	NPD4662	Approved
0.6378	Remote Similarity	NPD4661	Approved
0.6374	Remote Similarity	NPD4162	Approved
0.6373	Remote Similarity	NPD5525	Clinical (unspecified phase)
0.6358	Remote Similarity	NPD1794	Approved
0.6354	Remote Similarity	NPD3656	Approved
0.6344	Remote Similarity	NPD1975	Clinical (unspecified phase)
0.6335	Remote Similarity	NPD7318	Phase 3
0.6328	Remote Similarity	NPD3163	Approved
0.6328	Remote Similarity	NPD3162	Approved
0.6319	Remote Similarity	NPD7596	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD5355	Approved
0.6316	Remote Similarity	NPD5356	Approved
0.6313	Remote Similarity	NPD3052	Approved
0.6313	Remote Similarity	NPD3054	Approved
0.6305	Remote Similarity	NPD3863	Clinical (unspecified phase)
0.6294	Remote Similarity	NPD5605	Phase 2
0.629	Remote Similarity	NPD6419	Discontinued
0.6289	Remote Similarity	NPD2042	Clinical (unspecified phase)
0.6289	Remote Similarity	NPD2041	Clinical (unspecified phase)
0.6286	Remote Similarity	NPD2250	Discontinued
0.6284	Remote Similarity	NPD2459	Approved
0.6284	Remote Similarity	NPD2460	Phase 3
0.6284	Remote Similarity	NPD2458	Approved
0.6283	Remote Similarity	NPD3465	Clinical (unspecified phase)
0.6283	Remote Similarity	NPD7972	Discontinued
0.6277	Remote Similarity	NPD3687	Approved
0.6277	Remote Similarity	NPD3686	Approved
0.6271	Remote Similarity	NPD3056	Clinical (unspecified phase)
0.627	Remote Similarity	NPD3281	Clinical (unspecified phase)
0.6263	Remote Similarity	NPD6620	Discovery
0.6257	Remote Similarity	NPD52	Approved
0.6257	Remote Similarity	NPD7526	Approved
0.6257	Remote Similarity	NPD4186	Clinical (unspecified phase)
0.6257	Remote Similarity	NPD7527	Clinical (unspecified phase)
0.6243	Remote Similarity	NPD2649	Approved
0.6243	Remote Similarity	NPD2651	Approved
0.6236	Remote Similarity	NPD1726	Clinical (unspecified phase)
0.6236	Remote Similarity	NPD2245	Discovery
0.623	Remote Similarity	NPD4018	Clinical (unspecified phase)
0.623	Remote Similarity	NPD7153	Discontinued
0.623	Remote Similarity	NPD7317	Phase 3
0.6212	Remote Similarity	NPD3366	Approved
0.6209	Remote Similarity	NPD2161	Phase 2
0.6205	Remote Similarity	NPD2904	Discontinued
0.6203	Remote Similarity	NPD2874	Phase 2
0.6201	Remote Similarity	NPD3597	Clinical (unspecified phase)
0.62	Remote Similarity	NPD5557	Phase 1
0.619	Remote Similarity	NPD4124	Clinical (unspecified phase)
0.6183	Remote Similarity	NPD5295	Discontinued
0.6165	Remote Similarity	NPD6377	Clinical (unspecified phase)
0.6162	Remote Similarity	NPD3451	Clinical (unspecified phase)
0.6158	Remote Similarity	NPD2614	Approved
0.6154	Remote Similarity	NPD4466	Phase 1
0.615	Remote Similarity	NPD6087	Phase 1
0.6149	Remote Similarity	NPD3676	Clinical (unspecified phase)
0.6145	Remote Similarity	NPD5745	Approved
0.6139	Remote Similarity	NPD1298	Discontinued
0.6138	Remote Similarity	NPD5586	Clinical (unspecified phase)
0.6133	Remote Similarity	NPD2653	Approved
0.6129	Remote Similarity	NPD2677	Approved
0.6127	Remote Similarity	NPD6851	Approved
0.6127	Remote Similarity	NPD6853	Approved
0.6124	Remote Similarity	NPD3136	Phase 2
0.6122	Remote Similarity	NPD4666	Phase 3
0.612	Remote Similarity	NPD5712	Approved
0.6117	Remote Similarity	NPD1771	Clinical (unspecified phase)
0.6114	Remote Similarity	NPD5772	Approved
0.6114	Remote Similarity	NPD5773	Approved
0.6108	Remote Similarity	NPD5061	Approved
0.6108	Remote Similarity	NPD5062	Approved
0.6108	Remote Similarity	NPD7132	Clinical (unspecified phase)
0.6102	Remote Similarity	NPD5266	Clinical (unspecified phase)
0.61	Remote Similarity	NPD2822	Clinical (unspecified phase)
0.61	Remote Similarity	NPD3909	Discontinued
0.6094	Remote Similarity	NPD6072	Discontinued
0.6094	Remote Similarity	NPD7118	Clinical (unspecified phase)
0.6089	Remote Similarity	NPD6297	Approved
0.6087	Remote Similarity	NPD7978	Discontinued
0.6087	Remote Similarity	NPD4258	Approved
0.6087	Remote Similarity	NPD4259	Approved
0.6085	Remote Similarity	NPD6390	Discontinued
0.6085	Remote Similarity	NPD2183	Approved
0.6085	Remote Similarity	NPD2676	Approved
0.6085	Remote Similarity	NPD2675	Approved
0.6085	Remote Similarity	NPD7613	Discontinued
0.6085	Remote Similarity	NPD2184	Approved
0.608	Remote Similarity	NPD4575	Clinical (unspecified phase)
0.6075	Remote Similarity	NPD1662	Clinical (unspecified phase)
0.6071	Remote Similarity	NPD5709	Phase 3
0.6068	Remote Similarity	NPD3857	Clinical (unspecified phase)
0.6066	Remote Similarity	NPD2154	Approved
0.6066	Remote Similarity	NPD2156	Approved
0.6066	Remote Similarity	NPD2155	Approved
0.6059	Remote Similarity	NPD7038	Approved
0.6059	Remote Similarity	NPD7039	Approved
0.6057	Remote Similarity	NPD2428	Approved
0.6057	Remote Similarity	NPD2429	Approved
0.6057	Remote Similarity	NPD3685	Discontinued
0.6054	Remote Similarity	NPD6681	Discovery
0.6053	Remote Similarity	NPD8059	Phase 3
0.6053	Remote Similarity	NPD8058	Clinical (unspecified phase)
0.6043	Remote Similarity	NPD5160	Discontinued
0.6034	Remote Similarity	NPD5746	Approved
0.6032	Remote Similarity	NPD681	Clinical (unspecified phase)
0.6032	Remote Similarity	NPD3158	Phase 1
0.6032	Remote Similarity	NPD3157	Approved
0.6031	Remote Similarity	NPD2978	Approved
0.6031	Remote Similarity	NPD2977	Approved
0.603	Remote Similarity	NPD2215	Approved
0.603	Remote Similarity	NPD2216	Approved
0.6029	Remote Similarity	NPD2802	Phase 3
0.6029	Remote Similarity	NPD3936	Clinical (unspecified phase)
0.6023	Remote Similarity	NPD196	Phase 1
0.6022	Remote Similarity	NPD3060	Approved
0.6012	Remote Similarity	NPD2554	Approved
0.6012	Remote Similarity	NPD821	Approved
0.6012	Remote Similarity	NPD2556	Approved
0.6009	Remote Similarity	NPD7811	Phase 3
0.6009	Remote Similarity	NPD7810	Phase 3
0.6	Remote Similarity	NPD5967	Approved
0.6	Remote Similarity	NPD2186	Approved
0.6	Remote Similarity	NPD6863	Phase 2
0.599	Remote Similarity	NPD6862	Phase 2
0.599	Remote Similarity	NPD6089	Clinical (unspecified phase)
0.599	Remote Similarity	NPD5313	Approved
0.599	Remote Similarity	NPD5312	Approved
0.5979	Remote Similarity	NPD1774	Approved
0.5979	Remote Similarity	NPD3007	Approved
0.5979	Remote Similarity	NPD2515	Approved
0.5972	Remote Similarity	NPD4413	Clinical (unspecified phase)
0.5972	Remote Similarity	NPD7256	Discontinued
0.5969	Remote Similarity	NPD1670	Discontinued
0.5968	Remote Similarity	NPD3655	Clinical (unspecified phase)
0.5967	Remote Similarity	NPD3531	Approved
0.5967	Remote Similarity	NPD3530	Approved
0.5967	Remote Similarity	NPD3532	Approved
0.5962	Remote Similarity	NPD3490	Discontinued
0.5962	Remote Similarity	NPD7693	Approved
0.5959	Remote Similarity	NPD2592	Discontinued
0.5959	Remote Similarity	NPD3679	Phase 2
0.5956	Remote Similarity	NPD1772	Clinical (unspecified phase)
0.5955	Remote Similarity	NPD5647	Approved
0.595	Remote Similarity	NPD2388	Discontinued
0.595	Remote Similarity	NPD5137	Approved
0.5946	Remote Similarity	NPD6032	Approved
0.5946	Remote Similarity	NPD1422	Approved
0.5946	Remote Similarity	NPD3156	Discontinued
0.5939	Remote Similarity	NPD1307	Phase 2
0.5939	Remote Similarity	NPD8070	Approved
0.5939	Remote Similarity	NPD1309	Phase 2
0.5934	Remote Similarity	NPD5837	Clinical (unspecified phase)
0.5928	Remote Similarity	NPD2513	Approved
0.5924	Remote Similarity	NPD1520	Approved
0.5924	Remote Similarity	NPD1521	Approved
0.5924	Remote Similarity	NPD1536	Approved
0.5918	Remote Similarity	NPD7080	Clinical (unspecified phase)
0.5918	Remote Similarity	NPD2296	Approved
0.5911	Remote Similarity	NPD6042	Phase 2
0.5911	Remote Similarity	NPD42	Phase 2
0.5909	Remote Similarity	NPD2235	Phase 2
0.5909	Remote Similarity	NPD8245	Clinical (unspecified phase)
0.5909	Remote Similarity	NPD2231	Phase 2
0.5907	Remote Similarity	NPD6519	Phase 2
0.5907	Remote Similarity	NPD824	Approved
0.59	Remote Similarity	NPD7315	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