NPASS Compound

Structure

NPC471326 OpenBabel07101718312D 26 27 0 0 1 0 0 0 0 0999 V2000 4.4690 2.2332 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3619 0.8211 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6608 -2.8004 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1418 -4.2806 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6280 0.7918 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1025 1.5078 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9969 1.4220 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9980 -0.1611 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0704 1.6904 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8433 -1.1132 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3923 -2.2979 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4285 -2.2590 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6383 -0.2310 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5078 1.2694 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6925 0.7538 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1253 1.4975 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2638 -1.8843 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5932 -1.7767 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8738 -2.6315 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3781 0.8874 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0776 -0.9615 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0750 -2.4724 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.8259 -2.4768 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3930 1.4669 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.5318 -3.5334 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 14 1 0 0 0 0 2 14 1 0 0 0 0 4 25 1 0 0 0 0 5 6 1 0 0 0 0 5 13 1 0 0 0 0 6 16 2 0 0 0 0 7 9 1 0 0 0 0 7 15 1 0 0 0 0 8 10 1 0 0 0 0 8 15 2 0 0 0 0 9 16 1 0 0 0 0 10 17 2 0 0 0 0 11 12 1 0 0 0 0 11 17 1 0 0 0 0 12 18 1 0 0 0 0 13 21 1 0 0 0 0 14 15 1 0 0 0 0 16 20 1 0 0 0 0 17 19 1 0 0 0 0 18 21 1 0 0 0 0 18 22 2 0 0 0 0 19 23 2 0 0 0 0 19 25 1 0 0 0 0 20 24 2 0 0 0 0 20 26 1 0 0 0 0 21 3 1 1 0 0 0 21 26 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	360.19
Volume:	382.792
LogP:	3.151
LogD:	2.816
LogS:	-3.648
# Rotatable Bonds:	3
TPSA:	69.67
# H-Bond Aceptor:	5
# H-Bond Donor:	0
# Rings:	2
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.7
Synthetic Accessibility Score:	5.057
Fsp3:	0.571
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.71
MDCK Permeability:	2.3409718778566457e-05
Pgp-inhibitor:	0.999
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.002
20% Bioavailability (F20%):	0.99
30% Bioavailability (F30%):	0.938

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.161
Plasma Protein Binding (PPB):	92.85262298583984%
Volume Distribution (VD):	1.374
Pgp-substrate:	6.957096099853516%

ADMET: Metabolism

CYP1A2-inhibitor:	0.611
CYP1A2-substrate:	0.787
CYP2C19-inhibitor:	0.829
CYP2C19-substrate:	0.872
CYP2C9-inhibitor:	0.895
CYP2C9-substrate:	0.208
CYP2D6-inhibitor:	0.732
CYP2D6-substrate:	0.118
CYP3A4-inhibitor:	0.891
CYP3A4-substrate:	0.71

ADMET: Excretion

Clearance (CL):	2.952
Half-life (T1/2):	0.843

ADMET: Toxicity

hERG Blockers:	0.019
Human Hepatotoxicity (H-HT):	0.275
Drug-inuced Liver Injury (DILI):	0.257
AMES Toxicity:	0.363
Rat Oral Acute Toxicity:	0.022
Maximum Recommended Daily Dose:	0.842
Skin Sensitization:	0.951
Carcinogencity:	0.385
Eye Corrosion:	0.271
Eye Irritation:	0.288
Respiratory Toxicity:	0.367

Download Data

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

Natural Product: NPC471326

Natural Product ID:	NPC471326
*Common Name:**	Ketoemblide
IUPAC Name:	methyl (4E,6Z,11S)-11-methyl-10,15-dioxo-4-propan-2-yl-16-oxabicyclo[9.3.2]hexadeca-1(14),4,6-triene-7-carboxylate
Synonyms:
Standard InCHIKey:	SSRWHVBVQPAITB-YJXXDLRASA-N
Standard InCHI:	InChI=1S/C21H28O5/c1-14(2)15-7-9-16-6-5-13-21(3,26-20(16)24)18(22)12-11-17(10-8-15)19(23)25-4/h6,8,10,14H,5,7,9,11-13H2,1-4H3/b15-8+,17-10-/t21-/m0/s1
SMILES:	COC(=O)/C/1=CC=C(/CCC2=CCC[C@](C(=O)CC1)(C)OC2=O)C(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2414204
PubChem CID:	73350688
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones

*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
NPO20809	Sarcophyton trocheliophorum	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[10923847]
NPO20809	Sarcophyton trocheliophorum	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[23859780]
NPO20809	Sarcophyton trocheliophorum	Species	Alcyoniidae	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
IC50	1

Activity Type	# Activity
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT178	Individual Protein	Protein-tyrosine phosphatase 1B	Homo sapiens	IC50	=	27200.0	nM	PMID[478419]

☑ 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 NPC471326 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	228
0.1-0.2	1540
0.2-0.3	6617
0.3-0.4	14878
0.4-0.5	11931
0.5-0.6	5489
0.6-0.7	1779
0.7-0.8	227
0.8-0.85	5
0.85-0.9	0
0.9-0.95	1
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC221231
0.9342	High Similarity	NPC180290
0.8353	Intermediate Similarity	NPC38576
0.8353	Intermediate Similarity	NPC279859
0.8235	Intermediate Similarity	NPC99395
0.8235	Intermediate Similarity	NPC197903
0.8095	Intermediate Similarity	NPC173609
0.8022	Intermediate Similarity	NPC474490
0.8	Intermediate Similarity	NPC170377
0.7978	Intermediate Similarity	NPC471818
0.7955	Intermediate Similarity	NPC469653
0.7955	Intermediate Similarity	NPC469628
0.7955	Intermediate Similarity	NPC475906
0.7955	Intermediate Similarity	NPC469631
0.7955	Intermediate Similarity	NPC471047
0.7931	Intermediate Similarity	NPC234038
0.7907	Intermediate Similarity	NPC149869
0.7901	Intermediate Similarity	NPC244166
0.7889	Intermediate Similarity	NPC45579
0.7857	Intermediate Similarity	NPC474510
0.7831	Intermediate Similarity	NPC128276
0.7791	Intermediate Similarity	NPC474703
0.7778	Intermediate Similarity	NPC469718
0.7778	Intermediate Similarity	NPC329857
0.7765	Intermediate Similarity	NPC42470
0.7753	Intermediate Similarity	NPC475902
0.7738	Intermediate Similarity	NPC472965
0.7738	Intermediate Similarity	NPC63649
0.7738	Intermediate Similarity	NPC264227
0.7727	Intermediate Similarity	NPC122502
0.7711	Intermediate Similarity	NPC316324
0.7711	Intermediate Similarity	NPC57744
0.7701	Intermediate Similarity	NPC196487
0.7701	Intermediate Similarity	NPC14575
0.7701	Intermediate Similarity	NPC474359
0.7692	Intermediate Similarity	NPC166110
0.7674	Intermediate Similarity	NPC474291
0.7674	Intermediate Similarity	NPC85772
0.7634	Intermediate Similarity	NPC474947
0.7619	Intermediate Similarity	NPC471220
0.7609	Intermediate Similarity	NPC165383
0.7609	Intermediate Similarity	NPC248193
0.7586	Intermediate Similarity	NPC53867
0.7579	Intermediate Similarity	NPC54843
0.7561	Intermediate Similarity	NPC476355
0.7558	Intermediate Similarity	NPC301477
0.7558	Intermediate Similarity	NPC471325
0.7558	Intermediate Similarity	NPC25684
0.7558	Intermediate Similarity	NPC281949
0.7558	Intermediate Similarity	NPC286229
0.7553	Intermediate Similarity	NPC301596
0.7553	Intermediate Similarity	NPC476275
0.7553	Intermediate Similarity	NPC299396
0.7553	Intermediate Similarity	NPC172998
0.7529	Intermediate Similarity	NPC471740
0.7529	Intermediate Similarity	NPC178277
0.7528	Intermediate Similarity	NPC261721
0.7528	Intermediate Similarity	NPC164393
0.7527	Intermediate Similarity	NPC469632
0.75	Intermediate Similarity	NPC193396
0.75	Intermediate Similarity	NPC265574
0.75	Intermediate Similarity	NPC476794
0.75	Intermediate Similarity	NPC219874
0.75	Intermediate Similarity	NPC238197
0.75	Intermediate Similarity	NPC20713
0.75	Intermediate Similarity	NPC470240
0.75	Intermediate Similarity	NPC232812
0.75	Intermediate Similarity	NPC32944
0.75	Intermediate Similarity	NPC65603
0.7473	Intermediate Similarity	NPC115179
0.7473	Intermediate Similarity	NPC212598
0.7473	Intermediate Similarity	NPC106040
0.7473	Intermediate Similarity	NPC95364
0.7473	Intermediate Similarity	NPC142159
0.747	Intermediate Similarity	NPC193351
0.747	Intermediate Similarity	NPC138408
0.747	Intermediate Similarity	NPC226669
0.7449	Intermediate Similarity	NPC25666
0.7449	Intermediate Similarity	NPC271059
0.7447	Intermediate Similarity	NPC234339
0.7447	Intermediate Similarity	NPC273197
0.7444	Intermediate Similarity	NPC478145
0.7419	Intermediate Similarity	NPC475302
0.7416	Intermediate Similarity	NPC474547
0.7416	Intermediate Similarity	NPC470177
0.7416	Intermediate Similarity	NPC261380
0.7412	Intermediate Similarity	NPC299235
0.7407	Intermediate Similarity	NPC67183
0.7407	Intermediate Similarity	NPC64234
0.7407	Intermediate Similarity	NPC37929
0.7403	Intermediate Similarity	NPC155849
0.7391	Intermediate Similarity	NPC476369
0.7391	Intermediate Similarity	NPC476437
0.7386	Intermediate Similarity	NPC475989
0.7386	Intermediate Similarity	NPC318468
0.7386	Intermediate Similarity	NPC222358
0.7381	Intermediate Similarity	NPC266159
0.7381	Intermediate Similarity	NPC40353
0.7381	Intermediate Similarity	NPC473223
0.7381	Intermediate Similarity	NPC123360
0.7381	Intermediate Similarity	NPC472967
0.7356	Intermediate Similarity	NPC141810
0.7349	Intermediate Similarity	NPC294434
0.7349	Intermediate Similarity	NPC140287
0.7349	Intermediate Similarity	NPC259599
0.7349	Intermediate Similarity	NPC474758
0.7349	Intermediate Similarity	NPC15499
0.7349	Intermediate Similarity	NPC117746
0.734	Intermediate Similarity	NPC148463
0.7333	Intermediate Similarity	NPC107787
0.7326	Intermediate Similarity	NPC469690
0.7326	Intermediate Similarity	NPC469620
0.7326	Intermediate Similarity	NPC469617
0.7326	Intermediate Similarity	NPC270126
0.7317	Intermediate Similarity	NPC163003
0.7317	Intermediate Similarity	NPC288667
0.7312	Intermediate Similarity	NPC472705
0.7303	Intermediate Similarity	NPC70424
0.7303	Intermediate Similarity	NPC243618
0.7303	Intermediate Similarity	NPC115786
0.7294	Intermediate Similarity	NPC471225
0.7294	Intermediate Similarity	NPC41780
0.7294	Intermediate Similarity	NPC187568
0.7284	Intermediate Similarity	NPC470693
0.7283	Intermediate Similarity	NPC284561
0.7263	Intermediate Similarity	NPC470978
0.7263	Intermediate Similarity	NPC470974
0.7263	Intermediate Similarity	NPC31021
0.7262	Intermediate Similarity	NPC155587
0.7253	Intermediate Similarity	NPC475703
0.7253	Intermediate Similarity	NPC471738
0.7253	Intermediate Similarity	NPC478144
0.7245	Intermediate Similarity	NPC476270
0.7245	Intermediate Similarity	NPC469851
0.7241	Intermediate Similarity	NPC47747
0.7241	Intermediate Similarity	NPC304795
0.7241	Intermediate Similarity	NPC302426
0.7241	Intermediate Similarity	NPC233377
0.7241	Intermediate Similarity	NPC223904
0.7234	Intermediate Similarity	NPC476049
0.7229	Intermediate Similarity	NPC135703
0.7229	Intermediate Similarity	NPC287878
0.7222	Intermediate Similarity	NPC96621
0.7222	Intermediate Similarity	NPC474369
0.7222	Intermediate Similarity	NPC78089
0.7222	Intermediate Similarity	NPC189311
0.7215	Intermediate Similarity	NPC470688
0.7209	Intermediate Similarity	NPC108816
0.7209	Intermediate Similarity	NPC474341
0.7209	Intermediate Similarity	NPC472960
0.7209	Intermediate Similarity	NPC93763
0.7204	Intermediate Similarity	NPC49342
0.7204	Intermediate Similarity	NPC77337
0.7204	Intermediate Similarity	NPC62815
0.7204	Intermediate Similarity	NPC316228
0.7204	Intermediate Similarity	NPC251385
0.7195	Intermediate Similarity	NPC475310
0.7195	Intermediate Similarity	NPC469660
0.7191	Intermediate Similarity	NPC39588
0.7191	Intermediate Similarity	NPC16488
0.7191	Intermediate Similarity	NPC475947
0.7191	Intermediate Similarity	NPC288281
0.7188	Intermediate Similarity	NPC473291
0.7176	Intermediate Similarity	NPC235906
0.7176	Intermediate Similarity	NPC27205
0.7174	Intermediate Similarity	NPC473658
0.7174	Intermediate Similarity	NPC474471
0.7174	Intermediate Similarity	NPC227379
0.7174	Intermediate Similarity	NPC153805
0.7172	Intermediate Similarity	NPC140591
0.7172	Intermediate Similarity	NPC303653
0.7172	Intermediate Similarity	NPC291500
0.7172	Intermediate Similarity	NPC197835
0.7172	Intermediate Similarity	NPC189609
0.716	Intermediate Similarity	NPC218477
0.716	Intermediate Similarity	NPC134385
0.7159	Intermediate Similarity	NPC325031
0.7159	Intermediate Similarity	NPC112868
0.7159	Intermediate Similarity	NPC10276
0.7159	Intermediate Similarity	NPC35089
0.7158	Intermediate Similarity	NPC121825
0.7158	Intermediate Similarity	NPC476596
0.7143	Intermediate Similarity	NPC469551
0.7143	Intermediate Similarity	NPC261253
0.7143	Intermediate Similarity	NPC472863
0.7143	Intermediate Similarity	NPC284902
0.7143	Intermediate Similarity	NPC316426
0.7143	Intermediate Similarity	NPC198314
0.7143	Intermediate Similarity	NPC220478
0.7143	Intermediate Similarity	NPC116575
0.7143	Intermediate Similarity	NPC315395
0.7143	Intermediate Similarity	NPC474045
0.7128	Intermediate Similarity	NPC284185
0.7126	Intermediate Similarity	NPC617
0.7126	Intermediate Similarity	NPC276647
0.7126	Intermediate Similarity	NPC622
0.7125	Intermediate Similarity	NPC142423
0.7125	Intermediate Similarity	NPC308294
0.7113	Intermediate Similarity	NPC47834
0.7111	Intermediate Similarity	NPC72464

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 NPC471326 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	234
0.1-0.2	1969
0.2-0.3	3905
0.3-0.4	2080
0.4-0.5	704
0.5-0.6	219
0.6-0.7	37
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
0.7294	Intermediate Similarity	NPD4756	Discovery
0.7079	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7079	Intermediate Similarity	NPD5209	Approved
0.7059	Intermediate Similarity	NPD8039	Approved
0.7	Intermediate Similarity	NPD2685	Clinical (unspecified phase)
0.6947	Remote Similarity	NPD5693	Phase 1
0.6842	Remote Similarity	NPD5692	Phase 3
0.6771	Remote Similarity	NPD6050	Approved
0.6771	Remote Similarity	NPD5694	Approved
0.6667	Remote Similarity	NPD1694	Approved
0.6667	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6632	Remote Similarity	NPD5737	Approved
0.6632	Remote Similarity	NPD6672	Approved
0.6566	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6562	Remote Similarity	NPD6673	Approved
0.6562	Remote Similarity	NPD6904	Approved
0.6562	Remote Similarity	NPD6080	Approved
0.6535	Remote Similarity	NPD5696	Approved
0.6506	Remote Similarity	NPD7331	Phase 2
0.6506	Remote Similarity	NPD6108	Clinical (unspecified phase)
0.6495	Remote Similarity	NPD5785	Approved
0.6495	Remote Similarity	NPD46	Approved
0.6495	Remote Similarity	NPD6698	Approved
0.6415	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.64	Remote Similarity	NPD5695	Phase 3
0.64	Remote Similarity	NPD5654	Approved
0.6392	Remote Similarity	NPD1695	Approved
0.6354	Remote Similarity	NPD3573	Approved
0.6327	Remote Similarity	NPD7838	Discovery
0.6316	Remote Similarity	NPD5363	Approved
0.6277	Remote Similarity	NPD7154	Phase 3
0.6275	Remote Similarity	NPD6083	Phase 2
0.6275	Remote Similarity	NPD6084	Phase 2
0.6275	Remote Similarity	NPD5959	Approved
0.6263	Remote Similarity	NPD7983	Approved
0.625	Remote Similarity	NPD6098	Approved
0.6214	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.62	Remote Similarity	NPD5778	Approved
0.62	Remote Similarity	NPD5779	Approved
0.619	Remote Similarity	NPD7341	Phase 2
0.617	Remote Similarity	NPD6435	Approved
0.6162	Remote Similarity	NPD5207	Approved
0.6145	Remote Similarity	NPD2664	Clinical (unspecified phase)
0.6129	Remote Similarity	NPD4695	Discontinued
0.6111	Remote Similarity	NPD6614	Approved
0.6111	Remote Similarity	NPD5697	Approved
0.6105	Remote Similarity	NPD5362	Discontinued
0.6091	Remote Similarity	NPD2067	Discontinued
0.6091	Remote Similarity	NPD6371	Approved
0.6087	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6082	Remote Similarity	NPD7521	Approved
0.6082	Remote Similarity	NPD5786	Approved
0.6082	Remote Similarity	NPD7334	Approved
0.6082	Remote Similarity	NPD6409	Approved
0.6082	Remote Similarity	NPD5330	Approved
0.6082	Remote Similarity	NPD7146	Approved
0.6082	Remote Similarity	NPD6684	Approved
0.6071	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.6064	Remote Similarity	NPD5369	Approved
0.6061	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6061	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6061	Remote Similarity	NPD6101	Approved
0.6055	Remote Similarity	NPD6881	Approved
0.6055	Remote Similarity	NPD6899	Approved
0.6055	Remote Similarity	NPD6011	Approved
0.6019	Remote Similarity	NPD5739	Approved
0.6019	Remote Similarity	NPD7732	Phase 3
0.6019	Remote Similarity	NPD6402	Approved
0.6019	Remote Similarity	NPD6675	Approved
0.6019	Remote Similarity	NPD7839	Suspended
0.6019	Remote Similarity	NPD7128	Approved
0.6	Remote Similarity	NPD4269	Approved
0.6	Remote Similarity	NPD6014	Approved
0.6	Remote Similarity	NPD4270	Approved
0.6	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.6	Remote Similarity	NPD6013	Approved
0.6	Remote Similarity	NPD6012	Approved
0.5979	Remote Similarity	NPD1696	Phase 3
0.5979	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.5963	Remote Similarity	NPD5701	Approved
0.596	Remote Similarity	NPD5208	Approved
0.596	Remote Similarity	NPD6903	Approved
0.596	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.5957	Remote Similarity	NPD5368	Approved
0.5946	Remote Similarity	NPD7102	Approved
0.5946	Remote Similarity	NPD7290	Approved
0.5946	Remote Similarity	NPD6883	Approved
0.5941	Remote Similarity	NPD6411	Approved
0.5941	Remote Similarity	NPD5284	Approved
0.5941	Remote Similarity	NPD5281	Approved
0.593	Remote Similarity	NPD3704	Approved
0.5922	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.5922	Remote Similarity	NPD4629	Approved
0.5922	Remote Similarity	NPD5210	Approved
0.5918	Remote Similarity	NPD4694	Approved
0.5918	Remote Similarity	NPD5279	Phase 3
0.5918	Remote Similarity	NPD5280	Approved
0.5909	Remote Similarity	NPD7320	Approved
0.5893	Remote Similarity	NPD6847	Approved
0.5893	Remote Similarity	NPD8130	Phase 1
0.5893	Remote Similarity	NPD6869	Approved
0.5893	Remote Similarity	NPD6649	Approved
0.5893	Remote Similarity	NPD6617	Approved
0.5893	Remote Similarity	NPD6650	Approved
0.5856	Remote Similarity	NPD6372	Approved
0.5856	Remote Similarity	NPD6373	Approved
0.5849	Remote Similarity	NPD6648	Approved
0.5841	Remote Similarity	NPD6882	Approved
0.5841	Remote Similarity	NPD8297	Approved
0.5841	Remote Similarity	NPD6053	Discontinued
0.5826	Remote Similarity	NPD690	Clinical (unspecified phase)
0.5825	Remote Similarity	NPD7900	Approved
0.5825	Remote Similarity	NPD5282	Discontinued
0.5825	Remote Similarity	NPD7748	Approved
0.5825	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.5806	Remote Similarity	NPD7260	Phase 2
0.5789	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.5789	Remote Similarity	NPD4819	Approved
0.5789	Remote Similarity	NPD4252	Approved
0.5789	Remote Similarity	NPD4821	Approved
0.5789	Remote Similarity	NPD4822	Approved
0.5789	Remote Similarity	NPD4820	Approved
0.5789	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.578	Remote Similarity	NPD5909	Discontinued
0.5773	Remote Similarity	NPD6110	Phase 1
0.5769	Remote Similarity	NPD29	Approved
0.5769	Remote Similarity	NPD28	Approved
0.5769	Remote Similarity	NPD6927	Phase 3
0.5766	Remote Similarity	NPD6686	Approved
0.5758	Remote Similarity	NPD6422	Discontinued
0.5758	Remote Similarity	NPD5690	Phase 2
0.5755	Remote Similarity	NPD7638	Approved
0.5755	Remote Similarity	NPD4225	Approved
0.5752	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.5743	Remote Similarity	NPD4753	Phase 2
0.5714	Remote Similarity	NPD4197	Approved
0.5714	Remote Similarity	NPD7614	Phase 1
0.5701	Remote Similarity	NPD7639	Approved
0.5701	Remote Similarity	NPD7640	Approved
0.5698	Remote Similarity	NPD3197	Phase 1
0.569	Remote Similarity	NPD6274	Approved
0.5688	Remote Similarity	NPD6647	Phase 2
0.5673	Remote Similarity	NPD5122	Clinical (unspecified phase)
0.5673	Remote Similarity	NPD6001	Approved
0.566	Remote Similarity	NPD7902	Approved
0.5657	Remote Similarity	NPD5329	Approved
0.5656	Remote Similarity	NPD6637	Approved
0.5652	Remote Similarity	NPD4058	Approved
0.5647	Remote Similarity	NPD4194	Approved
0.5647	Remote Similarity	NPD4191	Approved
0.5647	Remote Similarity	NPD4193	Approved
0.5647	Remote Similarity	NPD4192	Approved
0.5641	Remote Similarity	NPD7115	Discovery
0.5641	Remote Similarity	NPD6317	Approved
0.5631	Remote Similarity	NPD7515	Phase 2
0.563	Remote Similarity	NPD7299	Clinical (unspecified phase)
0.5625	Remote Similarity	NPD3172	Approved
0.5614	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.5614	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.5614	Remote Similarity	NPD7116	Clinical (unspecified phase)
0.5612	Remote Similarity	NPD5332	Approved
0.5612	Remote Similarity	NPD5331	Approved
0.5604	Remote Similarity	NPD5276	Approved
0.56	Remote Similarity	NPD4519	Discontinued
0.56	Remote Similarity	NPD4623	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