NPASS Compound

Structure

NPC266514 OpenBabel07101719152D 28 29 0 0 1 0 0 0 0 0999 V2000 6.9282 -4.0000 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 5.1962 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -3.5000 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 5.1962 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -0.5000 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 0.0000 -2.0000 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 3.4641 1.0000 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 4.3301 2.5000 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 2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 C 0 0 2 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 0.8660 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.3301 3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 2.0000 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 4 1 0 0 0 0 2 13 1 0 0 0 0 3 14 1 0 0 0 0 4 5 1 0 0 0 0 5 6 1 0 0 0 0 6 7 1 0 0 0 0 7 8 1 0 0 0 0 8 9 2 0 0 0 0 9 15 1 0 0 0 0 10 11 1 0 0 0 0 10 13 2 0 0 0 0 12 16 1 0 0 0 0 12 27 1 0 0 0 0 13 20 1 0 0 0 0 14 22 2 0 0 0 0 14 27 1 0 0 0 0 15 16 2 0 0 0 0 15 18 1 0 0 0 0 16 17 1 0 0 0 0 17 19 1 0 0 0 0 17 23 1 6 0 0 0 18 21 1 0 0 0 0 18 24 2 0 0 0 0 19 21 1 1 0 0 0 19 28 1 0 0 0 0 20 25 2 0 0 0 0 20 26 1 0 0 0 0 21 11 1 1 0 0 0 21 28 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	392.18
Volume:	400.372
LogP:	3.268
LogD:	1.046
LogS:	-2.484
# Rotatable Bonds:	11
TPSA:	110.27
# H-Bond Aceptor:	7
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.263
Synthetic Accessibility Score:	4.873
Fsp3:	0.619
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.04
MDCK Permeability:	3.2815565646160394e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.043
20% Bioavailability (F20%):	0.008
30% Bioavailability (F30%):	0.007

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.348
Plasma Protein Binding (PPB):	88.11432647705078%
Volume Distribution (VD):	0.59
Pgp-substrate:	27.48509407043457%

ADMET: Metabolism

CYP1A2-inhibitor:	0.008
CYP1A2-substrate:	0.114
CYP2C19-inhibitor:	0.019
CYP2C19-substrate:	0.353
CYP2C9-inhibitor:	0.009
CYP2C9-substrate:	0.335
CYP2D6-inhibitor:	0.009
CYP2D6-substrate:	0.097
CYP3A4-inhibitor:	0.031
CYP3A4-substrate:	0.088

ADMET: Excretion

Clearance (CL):	2.629
Half-life (T1/2):	0.859

ADMET: Toxicity

hERG Blockers:	0.009
Human Hepatotoxicity (H-HT):	0.116
Drug-inuced Liver Injury (DILI):	0.936
AMES Toxicity:	0.018
Rat Oral Acute Toxicity:	0.908
Maximum Recommended Daily Dose:	0.007
Skin Sensitization:	0.184
Carcinogencity:	0.361
Eye Corrosion:	0.943
Eye Irritation:	0.478
Respiratory Toxicity:	0.308

Download Data

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

Natural Product: NPC266514

Natural Product ID:	NPC266514
*Common Name:**	4-((1R,5R,6R)-4-(Acetoxymethyl)-3-(Hept-1-Enyl)-5-Hydroxy-2-Oxo-7-Oxabicyclo[4.1.0]Hept-3-En-1-Yl)-2-Methylbut-2-Enoic Acid
IUPAC Name:	(E)-4-[(1R,2R,6R)-3-(acetyloxymethyl)-4-[(E)-hept-1-enyl]-2-hydroxy-5-oxo-7-oxabicyclo[4.1.0]hept-3-en-6-yl]-2-methylbut-2-enoic acid
Synonyms:
Standard InCHIKey:	FUWUXINGPGJNLY-XCWDVTCQSA-N
Standard InCHI:	InChI=1S/C21H28O7/c1-4-5-6-7-8-9-15-16(12-27-14(3)22)17(23)19-21(28-19,18(15)24)11-10-13(2)20(25)26/h8-10,17,19,23H,4-7,11-12H2,1-3H3,(H,25,26)/b9-8+,13-10+/t17-,19-,21+/m1/s1
SMILES:	CCCCC/C=C/C1=C(COC(=O)C)[C@@H](O)[C@@H]2[C@@](C1=O)(C/C=C(/C(=O)O)C)O2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL559847
PubChem CID:	25195250
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0003909] Fatty Acyls [CHEMONTID:0000262] Fatty acids and conjugates [CHEMONTID:0001989] Heterocyclic fatty acids

*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
NPO33175	Pestalotiopsis sp.	Species	Sporocadaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19117486]
NPO33175	Pestalotiopsis sp.	Species	Sporocadaceae	Eukaryota	chinese mangrove plant Rhizophora mucronata	n.a.	n.a.	PMID[19271764]
NPO33175	Pestalotiopsis sp.	Species	Sporocadaceae	Eukaryota	Chinese mangrove plant Rhizophoramucronata	n.a.	n.a.	PMID[19762244]
NPO33175	Pestalotiopsis sp.	Species	Sporocadaceae	Eukaryota	Isolated from the branches of Podocarpus macrophyllus	Kunming World Horticultural Exposition Garden, Kunming, China	2002-NOV	PMID[21302965]
NPO33175	Pestalotiopsis sp.	Species	Sporocadaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24168147]

☑ 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
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	IC50	=	27800.0	nM	PMID[549973]

☑ 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 NPC266514 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	229
0.1-0.2	1279
0.2-0.3	4420
0.3-0.4	7933
0.4-0.5	16059
0.5-0.6	8355
0.6-0.7	3485
0.7-0.8	864
0.8-0.85	58
0.85-0.9	8
0.9-0.95	2
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
0.9694	High Similarity	NPC118902
0.9694	High Similarity	NPC104161
0.9694	High Similarity	NPC469980
0.932	High Similarity	NPC89408
0.92	High Similarity	NPC39996
0.8762	High Similarity	NPC264819
0.8673	High Similarity	NPC142838
0.8519	High Similarity	NPC317107
0.8491	Intermediate Similarity	NPC469853
0.844	Intermediate Similarity	NPC317687
0.8241	Intermediate Similarity	NPC322903
0.819	Intermediate Similarity	NPC474339
0.819	Intermediate Similarity	NPC164598
0.8173	Intermediate Similarity	NPC161855
0.8155	Intermediate Similarity	NPC473291
0.8136	Intermediate Similarity	NPC471940
0.8056	Intermediate Similarity	NPC469852
0.8053	Intermediate Similarity	NPC270478
0.8051	Intermediate Similarity	NPC471939
0.8036	Intermediate Similarity	NPC469454
0.8036	Intermediate Similarity	NPC469463
0.8036	Intermediate Similarity	NPC469496
0.802	Intermediate Similarity	NPC477684
0.8018	Intermediate Similarity	NPC304180
0.8018	Intermediate Similarity	NPC179798
0.8017	Intermediate Similarity	NPC67569
0.8	Intermediate Similarity	NPC87335
0.7982	Intermediate Similarity	NPC474716
0.7981	Intermediate Similarity	NPC279722
0.798	Intermediate Similarity	NPC196381
0.7966	Intermediate Similarity	NPC473709
0.7966	Intermediate Similarity	NPC473919
0.7963	Intermediate Similarity	NPC474741
0.7959	Intermediate Similarity	NPC469809
0.7949	Intermediate Similarity	NPC470265
0.7949	Intermediate Similarity	NPC23786
0.7944	Intermediate Similarity	NPC471148
0.7928	Intermediate Similarity	NPC115257
0.7928	Intermediate Similarity	NPC161816
0.7928	Intermediate Similarity	NPC5103
0.7925	Intermediate Similarity	NPC475053
0.7925	Intermediate Similarity	NPC469551
0.7917	Intermediate Similarity	NPC236999
0.7913	Intermediate Similarity	NPC475130
0.7913	Intermediate Similarity	NPC284707
0.7913	Intermediate Similarity	NPC474286
0.7909	Intermediate Similarity	NPC474664
0.7909	Intermediate Similarity	NPC233379
0.7909	Intermediate Similarity	NPC327106
0.7909	Intermediate Similarity	NPC14862
0.789	Intermediate Similarity	NPC477125
0.7881	Intermediate Similarity	NPC469789
0.7881	Intermediate Similarity	NPC473802
0.7879	Intermediate Similarity	NPC187529
0.7876	Intermediate Similarity	NPC56448
0.787	Intermediate Similarity	NPC475945
0.787	Intermediate Similarity	NPC475871
0.785	Intermediate Similarity	NPC201718
0.785	Intermediate Similarity	NPC476270
0.785	Intermediate Similarity	NPC112613
0.785	Intermediate Similarity	NPC207885
0.7838	Intermediate Similarity	NPC15218
0.7838	Intermediate Similarity	NPC475922
0.7838	Intermediate Similarity	NPC38154
0.7826	Intermediate Similarity	NPC98249
0.7826	Intermediate Similarity	NPC53396
0.7826	Intermediate Similarity	NPC469684
0.7818	Intermediate Similarity	NPC326994
0.7818	Intermediate Similarity	NPC72813
0.7818	Intermediate Similarity	NPC194620
0.7818	Intermediate Similarity	NPC324327
0.7818	Intermediate Similarity	NPC477513
0.7818	Intermediate Similarity	NPC474421
0.7798	Intermediate Similarity	NPC296950
0.7798	Intermediate Similarity	NPC146731
0.7788	Intermediate Similarity	NPC66108
0.7788	Intermediate Similarity	NPC121825
0.7788	Intermediate Similarity	NPC473877
0.7778	Intermediate Similarity	NPC149371
0.7778	Intermediate Similarity	NPC475885
0.7778	Intermediate Similarity	NPC474747
0.7767	Intermediate Similarity	NPC114345
0.7767	Intermediate Similarity	NPC32552
0.7767	Intermediate Similarity	NPC6099
0.7767	Intermediate Similarity	NPC303230
0.7767	Intermediate Similarity	NPC327760
0.7759	Intermediate Similarity	NPC50774
0.7759	Intermediate Similarity	NPC709
0.7759	Intermediate Similarity	NPC186525
0.7757	Intermediate Similarity	NPC288876
0.7757	Intermediate Similarity	NPC324667
0.7757	Intermediate Similarity	NPC475949
0.7755	Intermediate Similarity	NPC253364
0.775	Intermediate Similarity	NPC293112
0.7748	Intermediate Similarity	NPC102843
0.7748	Intermediate Similarity	NPC151393
0.7748	Intermediate Similarity	NPC55972
0.7748	Intermediate Similarity	NPC327286
0.7748	Intermediate Similarity	NPC169888
0.7739	Intermediate Similarity	NPC477509
0.7736	Intermediate Similarity	NPC40812
0.7731	Intermediate Similarity	NPC120724
0.7727	Intermediate Similarity	NPC9303
0.7727	Intermediate Similarity	NPC475802
0.7727	Intermediate Similarity	NPC16313
0.7724	Intermediate Similarity	NPC476193
0.7719	Intermediate Similarity	NPC477126
0.7719	Intermediate Similarity	NPC159333
0.7714	Intermediate Similarity	NPC14961
0.7714	Intermediate Similarity	NPC270013
0.7706	Intermediate Similarity	NPC472755
0.7706	Intermediate Similarity	NPC473624
0.7706	Intermediate Similarity	NPC159533
0.7692	Intermediate Similarity	NPC156745
0.7692	Intermediate Similarity	NPC236918
0.7692	Intermediate Similarity	NPC469692
0.7692	Intermediate Similarity	NPC469645
0.7685	Intermediate Similarity	NPC128733
0.7685	Intermediate Similarity	NPC472753
0.7685	Intermediate Similarity	NPC474742
0.7685	Intermediate Similarity	NPC133907
0.7685	Intermediate Similarity	NPC469851
0.7685	Intermediate Similarity	NPC110443
0.7685	Intermediate Similarity	NPC47880
0.7685	Intermediate Similarity	NPC185141
0.7685	Intermediate Similarity	NPC46998
0.7672	Intermediate Similarity	NPC470492
0.7672	Intermediate Similarity	NPC471146
0.7672	Intermediate Similarity	NPC183580
0.7672	Intermediate Similarity	NPC167606
0.7672	Intermediate Similarity	NPC23046
0.7672	Intermediate Similarity	NPC140055
0.7672	Intermediate Similarity	NPC20302
0.7672	Intermediate Similarity	NPC312824
0.7672	Intermediate Similarity	NPC286528
0.7672	Intermediate Similarity	NPC471145
0.7672	Intermediate Similarity	NPC470493
0.7667	Intermediate Similarity	NPC24651
0.7667	Intermediate Similarity	NPC172154
0.7667	Intermediate Similarity	NPC470922
0.7667	Intermediate Similarity	NPC8374
0.7667	Intermediate Similarity	NPC8369
0.7667	Intermediate Similarity	NPC145238
0.7667	Intermediate Similarity	NPC81736
0.7664	Intermediate Similarity	NPC471144
0.7664	Intermediate Similarity	NPC83895
0.7664	Intermediate Similarity	NPC187761
0.7664	Intermediate Similarity	NPC300584
0.7664	Intermediate Similarity	NPC264378
0.7664	Intermediate Similarity	NPC222303
0.7658	Intermediate Similarity	NPC469558
0.7653	Intermediate Similarity	NPC159714
0.7653	Intermediate Similarity	NPC221510
0.7652	Intermediate Similarity	NPC305044
0.7652	Intermediate Similarity	NPC265290
0.7652	Intermediate Similarity	NPC80650
0.7642	Intermediate Similarity	NPC57664
0.7642	Intermediate Similarity	NPC230800
0.7642	Intermediate Similarity	NPC279621
0.7642	Intermediate Similarity	NPC472995
0.7636	Intermediate Similarity	NPC471143
0.7636	Intermediate Similarity	NPC475676
0.7636	Intermediate Similarity	NPC477510
0.7636	Intermediate Similarity	NPC220964
0.7636	Intermediate Similarity	NPC472756
0.7632	Intermediate Similarity	NPC476801
0.7632	Intermediate Similarity	NPC269530
0.7627	Intermediate Similarity	NPC19336
0.7627	Intermediate Similarity	NPC185876
0.7627	Intermediate Similarity	NPC474370
0.7627	Intermediate Similarity	NPC472759
0.7627	Intermediate Similarity	NPC329080
0.7619	Intermediate Similarity	NPC474035
0.7619	Intermediate Similarity	NPC81386
0.7615	Intermediate Similarity	NPC291500
0.7615	Intermediate Similarity	NPC472754
0.7615	Intermediate Similarity	NPC140591
0.7615	Intermediate Similarity	NPC197835
0.7615	Intermediate Similarity	NPC303653
0.7615	Intermediate Similarity	NPC478176
0.7615	Intermediate Similarity	NPC473596
0.7615	Intermediate Similarity	NPC189609
0.7611	Intermediate Similarity	NPC235014
0.7611	Intermediate Similarity	NPC281624
0.7607	Intermediate Similarity	NPC251310
0.7607	Intermediate Similarity	NPC472760
0.7603	Intermediate Similarity	NPC225049
0.76	Intermediate Similarity	NPC100017
0.76	Intermediate Similarity	NPC475154
0.76	Intermediate Similarity	NPC475500
0.76	Intermediate Similarity	NPC182266
0.76	Intermediate Similarity	NPC471137
0.76	Intermediate Similarity	NPC471136
0.76	Intermediate Similarity	NPC223356
0.76	Intermediate Similarity	NPC473548
0.7589	Intermediate Similarity	NPC472439
0.7589	Intermediate Similarity	NPC469916
0.7586	Intermediate Similarity	NPC474333
0.7583	Intermediate Similarity	NPC11895
0.7583	Intermediate Similarity	NPC67251

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 NPC266514 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	202
0.1-0.2	1678
0.2-0.3	3585
0.3-0.4	2361
0.4-0.5	953
0.5-0.6	308
0.6-0.7	52
0.7-0.8	10
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7672	Intermediate Similarity	NPD7115	Discovery
0.767	Intermediate Similarity	NPD7838	Discovery
0.7523	Intermediate Similarity	NPD5344	Discontinued
0.75	Intermediate Similarity	NPD46	Approved
0.75	Intermediate Similarity	NPD6698	Approved
0.7431	Intermediate Similarity	NPD6648	Approved
0.7339	Intermediate Similarity	NPD4225	Approved
0.7304	Intermediate Similarity	NPD6371	Approved
0.7264	Intermediate Similarity	NPD7983	Approved
0.7193	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD6319	Approved
0.7182	Intermediate Similarity	NPD8029	Clinical (unspecified phase)
0.7131	Intermediate Similarity	NPD8516	Approved
0.7131	Intermediate Similarity	NPD8515	Approved
0.7131	Intermediate Similarity	NPD8517	Approved
0.7131	Intermediate Similarity	NPD8513	Phase 3
0.7069	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD5779	Approved
0.7037	Intermediate Similarity	NPD5778	Approved
0.6983	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6864	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.685	Remote Similarity	NPD8074	Phase 3
0.6833	Remote Similarity	NPD4632	Approved
0.6825	Remote Similarity	NPD7492	Approved
0.6807	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD6054	Approved
0.6772	Remote Similarity	NPD6616	Approved
0.6752	Remote Similarity	NPD5697	Approved
0.675	Remote Similarity	NPD8297	Approved
0.6746	Remote Similarity	NPD8328	Phase 3
0.6733	Remote Similarity	NPD4756	Discovery
0.672	Remote Similarity	NPD6015	Approved
0.672	Remote Similarity	NPD6016	Approved
0.6719	Remote Similarity	NPD7078	Approved
0.6695	Remote Similarity	NPD6899	Approved
0.6695	Remote Similarity	NPD6881	Approved
0.6667	Remote Similarity	NPD6650	Approved
0.6667	Remote Similarity	NPD6110	Phase 1
0.6667	Remote Similarity	NPD5282	Discontinued
0.6667	Remote Similarity	NPD6009	Approved
0.6667	Remote Similarity	NPD7639	Approved
0.6667	Remote Similarity	NPD5988	Approved
0.6667	Remote Similarity	NPD7640	Approved
0.6667	Remote Similarity	NPD6370	Approved
0.6667	Remote Similarity	NPD7736	Approved
0.6667	Remote Similarity	NPD6649	Approved
0.6639	Remote Similarity	NPD6012	Approved
0.6639	Remote Similarity	NPD6014	Approved
0.6639	Remote Similarity	NPD6013	Approved
0.6614	Remote Similarity	NPD7604	Phase 2
0.661	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6607	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6587	Remote Similarity	NPD5983	Phase 2
0.6583	Remote Similarity	NPD6883	Approved
0.6583	Remote Similarity	NPD4634	Approved
0.6583	Remote Similarity	NPD7102	Approved
0.6583	Remote Similarity	NPD7290	Approved
0.6579	Remote Similarity	NPD7638	Approved
0.6555	Remote Similarity	NPD6686	Approved
0.6555	Remote Similarity	NPD6011	Approved
0.6545	Remote Similarity	NPD5785	Approved
0.6542	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6542	Remote Similarity	NPD1696	Phase 3
0.6529	Remote Similarity	NPD6869	Approved
0.6529	Remote Similarity	NPD6617	Approved
0.6529	Remote Similarity	NPD8130	Phase 1
0.6529	Remote Similarity	NPD6847	Approved
0.6525	Remote Similarity	NPD6402	Approved
0.6525	Remote Similarity	NPD5739	Approved
0.6525	Remote Similarity	NPD7128	Approved
0.6525	Remote Similarity	NPD6675	Approved
0.6515	Remote Similarity	NPD7260	Phase 2
0.6512	Remote Similarity	NPD8273	Phase 1
0.6508	Remote Similarity	NPD6059	Approved
0.65	Remote Similarity	NPD6373	Approved
0.65	Remote Similarity	NPD6372	Approved
0.6484	Remote Similarity	NPD7642	Approved
0.6484	Remote Similarity	NPD7830	Approved
0.6484	Remote Similarity	NPD7829	Approved
0.6475	Remote Similarity	NPD6882	Approved
0.6471	Remote Similarity	NPD5701	Approved
0.6462	Remote Similarity	NPD8293	Discontinued
0.6457	Remote Similarity	NPD7503	Approved
0.6455	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6455	Remote Similarity	NPD6101	Approved
0.6417	Remote Similarity	NPD7320	Approved
0.6415	Remote Similarity	NPD5209	Approved
0.641	Remote Similarity	NPD5211	Phase 2
0.6404	Remote Similarity	NPD7839	Suspended
0.64	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6397	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6389	Remote Similarity	NPD1694	Approved
0.6389	Remote Similarity	NPD5363	Approved
0.6387	Remote Similarity	NPD6008	Approved
0.6385	Remote Similarity	NPD6336	Discontinued
0.6364	Remote Similarity	NPD7319	Approved
0.6341	Remote Similarity	NPD6053	Discontinued
0.6339	Remote Similarity	NPD6411	Approved
0.6328	Remote Similarity	NPD6921	Approved
0.6306	Remote Similarity	NPD1695	Approved
0.6303	Remote Similarity	NPD5141	Approved
0.627	Remote Similarity	NPD7500	Approved
0.626	Remote Similarity	NPD7507	Approved
0.6239	Remote Similarity	NPD4696	Approved
0.6239	Remote Similarity	NPD5285	Approved
0.6239	Remote Similarity	NPD5286	Approved
0.6226	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6207	Remote Similarity	NPD7902	Approved
0.6207	Remote Similarity	NPD6083	Phase 2
0.6207	Remote Similarity	NPD6084	Phase 2
0.6195	Remote Similarity	NPD7637	Suspended
0.619	Remote Similarity	NPD6274	Approved
0.6182	Remote Similarity	NPD4249	Approved
0.6174	Remote Similarity	NPD5695	Phase 3
0.6172	Remote Similarity	NPD7100	Approved
0.6172	Remote Similarity	NPD7101	Approved
0.6154	Remote Similarity	NPD5696	Approved
0.6142	Remote Similarity	NPD6317	Approved
0.6136	Remote Similarity	NPD8451	Approved
0.6134	Remote Similarity	NPD5224	Approved
0.6134	Remote Similarity	NPD7632	Discontinued
0.6134	Remote Similarity	NPD5226	Approved
0.6134	Remote Similarity	NPD4633	Approved
0.6134	Remote Similarity	NPD5225	Approved
0.6129	Remote Similarity	NPD7601	Clinical (unspecified phase)
0.6129	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6126	Remote Similarity	NPD4251	Approved
0.6126	Remote Similarity	NPD4250	Approved
0.6111	Remote Similarity	NPD4269	Approved
0.6111	Remote Similarity	NPD4270	Approved
0.6103	Remote Similarity	NPD6845	Suspended
0.6098	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6094	Remote Similarity	NPD6313	Approved
0.6094	Remote Similarity	NPD7328	Approved
0.6094	Remote Similarity	NPD7327	Approved
0.6094	Remote Similarity	NPD7641	Discontinued
0.6094	Remote Similarity	NPD6335	Approved
0.6094	Remote Similarity	NPD6314	Approved
0.609	Remote Similarity	NPD8448	Approved
0.6087	Remote Similarity	NPD7748	Approved
0.6083	Remote Similarity	NPD5175	Approved
0.6083	Remote Similarity	NPD5174	Approved
0.6077	Remote Similarity	NPD8444	Approved
0.6077	Remote Similarity	NPD8033	Approved
0.6075	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6075	Remote Similarity	NPD4252	Approved
0.6068	Remote Similarity	NPD4755	Approved
0.6066	Remote Similarity	NPD6412	Phase 2
0.6061	Remote Similarity	NPD8340	Approved
0.6061	Remote Similarity	NPD8342	Approved
0.6061	Remote Similarity	NPD8299	Approved
0.6061	Remote Similarity	NPD8341	Approved
0.6055	Remote Similarity	NPD7154	Phase 3
0.6053	Remote Similarity	NPD7515	Phase 2
0.605	Remote Similarity	NPD5223	Approved
0.6047	Remote Similarity	NPD7516	Approved
0.6045	Remote Similarity	NPD6033	Approved
0.6036	Remote Similarity	NPD5786	Approved
0.6019	Remote Similarity	NPD5369	Approved
0.6	Remote Similarity	NPD8294	Approved
0.6	Remote Similarity	NPD7116	Clinical (unspecified phase)
0.6	Remote Similarity	NPD6399	Phase 3
0.6	Remote Similarity	NPD8377	Approved
0.5983	Remote Similarity	NPD5221	Approved
0.5983	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.5983	Remote Similarity	NPD5222	Approved
0.5971	Remote Similarity	NPD8387	Clinical (unspecified phase)
0.5966	Remote Similarity	NPD4700	Approved
0.596	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.5959	Remote Similarity	NPD6190	Approved
0.5956	Remote Similarity	NPD5956	Approved
0.5956	Remote Similarity	NPD8390	Approved
0.5956	Remote Similarity	NPD8392	Approved
0.5956	Remote Similarity	NPD8391	Approved
0.5954	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.5954	Remote Similarity	NPD8296	Approved
0.5954	Remote Similarity	NPD8335	Approved
0.5954	Remote Similarity	NPD8380	Approved
0.5954	Remote Similarity	NPD8378	Approved
0.5954	Remote Similarity	NPD8379	Approved
0.5948	Remote Similarity	NPD7900	Approved
0.5948	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.5938	Remote Similarity	NPD6868	Approved
0.5932	Remote Similarity	NPD5173	Approved
0.5926	Remote Similarity	NPD4820	Approved
0.5926	Remote Similarity	NPD4822	Approved
0.5926	Remote Similarity	NPD4819	Approved
0.5926	Remote Similarity	NPD4821	Approved
0.592	Remote Similarity	NPD2067	Discontinued
0.5913	Remote Similarity	NPD5694	Approved
0.5913	Remote Similarity	NPD5284	Approved
0.5913	Remote Similarity	NPD5281	Approved
0.5913	Remote Similarity	NPD5693	Phase 1
0.5913	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.5905	Remote Similarity	NPD8039	Approved
0.5899	Remote Similarity	NPD8415	Approved
0.5897	Remote Similarity	NPD5210	Approved
0.5897	Remote Similarity	NPD4629	Approved
0.5893	Remote Similarity	NPD3618	Phase 1
0.5888	Remote Similarity	NPD4271	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