NPASS Compound

Structure

NPC104161 OpenBabel07101718252D 25 26 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 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 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 3.4641 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 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 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 3 1 0 0 0 0 2 12 1 0 0 0 0 3 4 1 0 0 0 0 4 5 1 0 0 0 0 5 6 2 0 0 0 0 6 7 1 0 0 0 0 7 8 2 0 0 0 0 8 13 1 0 0 0 0 9 10 1 0 0 0 0 9 12 2 0 0 0 0 11 14 1 0 0 0 0 11 20 1 0 0 0 0 12 18 1 0 0 0 0 13 14 2 0 0 0 0 13 16 1 0 0 0 0 14 15 1 0 0 0 0 15 17 1 0 0 0 0 15 21 1 6 0 0 0 16 19 1 0 0 0 0 16 22 2 0 0 0 0 17 19 1 1 0 0 0 17 25 1 0 0 0 0 18 23 2 0 0 0 0 18 24 1 0 0 0 0 19 10 1 1 0 0 0 19 25 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	348.16
Volume:	356.99
LogP:	2.704
LogD:	0.727
LogS:	-1.928
# Rotatable Bonds:	9
TPSA:	101.04
# H-Bond Aceptor:	6
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.296
Synthetic Accessibility Score:	5.11
Fsp3:	0.579
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.942
MDCK Permeability:	3.71909627574496e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.012
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.003

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.877
Plasma Protein Binding (PPB):	49.40580749511719%
Volume Distribution (VD):	0.691
Pgp-substrate:	39.54904556274414%

ADMET: Metabolism

CYP1A2-inhibitor:	0.006
CYP1A2-substrate:	0.34
CYP2C19-inhibitor:	0.02
CYP2C19-substrate:	0.217
CYP2C9-inhibitor:	0.004
CYP2C9-substrate:	0.352
CYP2D6-inhibitor:	0.004
CYP2D6-substrate:	0.094
CYP3A4-inhibitor:	0.028
CYP3A4-substrate:	0.074

ADMET: Excretion

Clearance (CL):	2.705
Half-life (T1/2):	0.787

ADMET: Toxicity

hERG Blockers:	0.005
Human Hepatotoxicity (H-HT):	0.054
Drug-inuced Liver Injury (DILI):	0.959
AMES Toxicity:	0.018
Rat Oral Acute Toxicity:	0.566
Maximum Recommended Daily Dose:	0.007
Skin Sensitization:	0.492
Carcinogencity:	0.158
Eye Corrosion:	0.98
Eye Irritation:	0.502
Respiratory Toxicity:	0.485

Download Data

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

Natural Product: NPC104161

Natural Product ID:	NPC104161
*Common Name:**	4-((1R,5R,6R)-3-(Hepta-1,3-Dienyl)-5-Hydroxy-4-(Hydroxymethyl)-2-Oxo-7-Oxabicyclo[4.1.0]Hept-3-En-1-Yl)-2-Methylbut-2-Enoic Acid
IUPAC Name:	(E)-4-[(1R,2R,6R)-4-[(1E,3E)-hepta-1,3-dienyl]-2-hydroxy-3-(hydroxymethyl)-5-oxo-7-oxabicyclo[4.1.0]hept-3-en-6-yl]-2-methylbut-2-enoic acid
Synonyms:
Standard InCHIKey:	JFPPAMKYTXBMED-QCHQCDEVSA-N
Standard InCHI:	InChI=1S/C19H24O6/c1-3-4-5-6-7-8-13-14(11-20)15(21)17-19(25-17,16(13)22)10-9-12(2)18(23)24/h5-9,15,17,20-21H,3-4,10-11H2,1-2H3,(H,23,24)/b6-5+,8-7+,12-9+/t15-,17-,19+/m1/s1
SMILES:	CCC/C=C/C=C/C1=C(CO)[C@H]([C@@H]2[C@](C/C=C(C)/C(=O)O)(C1=O)O2)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL559282
PubChem CID:	25207985
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	5

Activity Type	# Activity
Organism	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	IC50	>	50000.0	nM	PMID[473240]
NPT1118	Organism	Streptococcus pneumoniae	Streptococcus pneumoniae	IC50	>	50000.0	nM	PMID[473240]
NPT19	Organism	Escherichia coli	Escherichia coli	IC50	>	50000.0	nM	PMID[473240]
NPT20	Organism	Candida albicans	Candida albicans	IC50	>	50000.0	nM	PMID[473240]
NPT3594	Organism	Galactomyces geotrichum	Galactomyces geotrichum	IC50	>	50000.0	nM	PMID[473240]

☑ 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 NPC104161 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	1226
0.2-0.3	4632
0.3-0.4	8441
0.4-0.5	16142
0.5-0.6	8082
0.6-0.7	3282
0.7-0.8	630
0.8-0.85	27
0.85-0.9	8
0.9-0.95	1
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC118902
1.0	High Similarity	NPC469980
0.9694	High Similarity	NPC266514
0.9485	High Similarity	NPC39996
0.9029	High Similarity	NPC89408
0.8947	High Similarity	NPC142838
0.8654	High Similarity	NPC264819
0.8381	Intermediate Similarity	NPC469853
0.8265	Intermediate Similarity	NPC477684
0.8241	Intermediate Similarity	NPC317107
0.8229	Intermediate Similarity	NPC196381
0.8224	Intermediate Similarity	NPC87335
0.8211	Intermediate Similarity	NPC469809
0.8165	Intermediate Similarity	NPC317687
0.8125	Intermediate Similarity	NPC187529
0.8039	Intermediate Similarity	NPC279722
0.8	Intermediate Similarity	NPC253364
0.7963	Intermediate Similarity	NPC322903
0.7944	Intermediate Similarity	NPC469852
0.7905	Intermediate Similarity	NPC474339
0.7905	Intermediate Similarity	NPC164598
0.7895	Intermediate Similarity	NPC221510
0.7895	Intermediate Similarity	NPC159714
0.7885	Intermediate Similarity	NPC161855
0.7881	Intermediate Similarity	NPC471940
0.7864	Intermediate Similarity	NPC473291
0.783	Intermediate Similarity	NPC478176
0.781	Intermediate Similarity	NPC324667
0.7798	Intermediate Similarity	NPC327106
0.7798	Intermediate Similarity	NPC102843
0.7797	Intermediate Similarity	NPC471939
0.7788	Intermediate Similarity	NPC270478
0.7788	Intermediate Similarity	NPC20066
0.7778	Intermediate Similarity	NPC477125
0.7778	Intermediate Similarity	NPC472007
0.7768	Intermediate Similarity	NPC469454
0.7768	Intermediate Similarity	NPC469496
0.7768	Intermediate Similarity	NPC469463
0.7759	Intermediate Similarity	NPC67569
0.7757	Intermediate Similarity	NPC131366
0.7748	Intermediate Similarity	NPC304180
0.7748	Intermediate Similarity	NPC179798
0.7736	Intermediate Similarity	NPC112613
0.7736	Intermediate Similarity	NPC207885
0.7714	Intermediate Similarity	NPC300584
0.7712	Intermediate Similarity	NPC473919
0.7712	Intermediate Similarity	NPC473709
0.7706	Intermediate Similarity	NPC474716
0.7699	Intermediate Similarity	NPC80650
0.7692	Intermediate Similarity	NPC470265
0.7692	Intermediate Similarity	NPC23786
0.7685	Intermediate Similarity	NPC474741
0.7677	Intermediate Similarity	NPC472009
0.767	Intermediate Similarity	NPC121825
0.7667	Intermediate Similarity	NPC236999
0.7664	Intermediate Similarity	NPC471148
0.7658	Intermediate Similarity	NPC115257
0.7658	Intermediate Similarity	NPC161816
0.7658	Intermediate Similarity	NPC5103
0.7652	Intermediate Similarity	NPC251310
0.7652	Intermediate Similarity	NPC186525
0.7652	Intermediate Similarity	NPC709
0.7652	Intermediate Similarity	NPC284707
0.7652	Intermediate Similarity	NPC50774
0.7652	Intermediate Similarity	NPC474286
0.7652	Intermediate Similarity	NPC475130
0.7647	Intermediate Similarity	NPC225049
0.7647	Intermediate Similarity	NPC32552
0.7647	Intermediate Similarity	NPC476705
0.7642	Intermediate Similarity	NPC469551
0.7642	Intermediate Similarity	NPC475053
0.7636	Intermediate Similarity	NPC474664
0.7636	Intermediate Similarity	NPC233379
0.7636	Intermediate Similarity	NPC14862
0.7629	Intermediate Similarity	NPC47450
0.7627	Intermediate Similarity	NPC469789
0.7627	Intermediate Similarity	NPC473802
0.7619	Intermediate Similarity	NPC471916
0.7611	Intermediate Similarity	NPC56448
0.76	Intermediate Similarity	NPC471738
0.7593	Intermediate Similarity	NPC475871
0.7593	Intermediate Similarity	NPC472755
0.7593	Intermediate Similarity	NPC473624
0.7593	Intermediate Similarity	NPC475945
0.7589	Intermediate Similarity	NPC476023
0.7586	Intermediate Similarity	NPC268958
0.7583	Intermediate Similarity	NPC473253
0.7573	Intermediate Similarity	NPC469645
0.7573	Intermediate Similarity	NPC469692
0.757	Intermediate Similarity	NPC128733
0.757	Intermediate Similarity	NPC46998
0.757	Intermediate Similarity	NPC469851
0.757	Intermediate Similarity	NPC133907
0.757	Intermediate Similarity	NPC472753
0.757	Intermediate Similarity	NPC476270
0.757	Intermediate Similarity	NPC201718
0.757	Intermediate Similarity	NPC110443
0.757	Intermediate Similarity	NPC185141
0.7568	Intermediate Similarity	NPC15218
0.7568	Intermediate Similarity	NPC38154
0.7568	Intermediate Similarity	NPC475922
0.7565	Intermediate Similarity	NPC470493
0.7565	Intermediate Similarity	NPC156252
0.7565	Intermediate Similarity	NPC469684
0.7565	Intermediate Similarity	NPC183580
0.7565	Intermediate Similarity	NPC286528
0.7565	Intermediate Similarity	NPC20302
0.7565	Intermediate Similarity	NPC27999
0.7565	Intermediate Similarity	NPC477116
0.7565	Intermediate Similarity	NPC167606
0.7565	Intermediate Similarity	NPC53396
0.7565	Intermediate Similarity	NPC98249
0.7565	Intermediate Similarity	NPC470492
0.7565	Intermediate Similarity	NPC312824
0.7565	Intermediate Similarity	NPC140055
0.7563	Intermediate Similarity	NPC8374
0.7551	Intermediate Similarity	NPC477786
0.7551	Intermediate Similarity	NPC477784
0.7551	Intermediate Similarity	NPC477785
0.7547	Intermediate Similarity	NPC278008
0.7545	Intermediate Similarity	NPC474421
0.7545	Intermediate Similarity	NPC473284
0.7545	Intermediate Similarity	NPC324327
0.7545	Intermediate Similarity	NPC477513
0.7545	Intermediate Similarity	NPC72813
0.7545	Intermediate Similarity	NPC326994
0.7545	Intermediate Similarity	NPC194620
0.7525	Intermediate Similarity	NPC472008
0.7524	Intermediate Similarity	NPC57664
0.7523	Intermediate Similarity	NPC472756
0.7523	Intermediate Similarity	NPC146731
0.7523	Intermediate Similarity	NPC296950
0.7522	Intermediate Similarity	NPC473877
0.7522	Intermediate Similarity	NPC66108
0.7521	Intermediate Similarity	NPC475885
0.7521	Intermediate Similarity	NPC474370
0.75	Intermediate Similarity	NPC472754
0.75	Intermediate Similarity	NPC217624
0.75	Intermediate Similarity	NPC181393
0.75	Intermediate Similarity	NPC474747
0.75	Intermediate Similarity	NPC21326
0.75	Intermediate Similarity	NPC149371
0.75	Intermediate Similarity	NPC293112
0.748	Intermediate Similarity	NPC476193
0.7479	Intermediate Similarity	NPC120724
0.7478	Intermediate Similarity	NPC179626
0.7478	Intermediate Similarity	NPC477509
0.7478	Intermediate Similarity	NPC270929
0.7477	Intermediate Similarity	NPC288876
0.7477	Intermediate Similarity	NPC169888
0.7477	Intermediate Similarity	NPC55972
0.7477	Intermediate Similarity	NPC475949
0.7477	Intermediate Similarity	NPC327286
0.7477	Intermediate Similarity	NPC151393
0.7476	Intermediate Similarity	NPC114345
0.7476	Intermediate Similarity	NPC327760
0.7476	Intermediate Similarity	NPC6099
0.7476	Intermediate Similarity	NPC475441
0.7476	Intermediate Similarity	NPC303230
0.7474	Intermediate Similarity	NPC272267
0.7474	Intermediate Similarity	NPC97173
0.7459	Intermediate Similarity	NPC470880
0.7458	Intermediate Similarity	NPC472401
0.7456	Intermediate Similarity	NPC477126
0.7456	Intermediate Similarity	NPC159333
0.7456	Intermediate Similarity	NPC474271
0.7456	Intermediate Similarity	NPC198539
0.7455	Intermediate Similarity	NPC128828
0.7455	Intermediate Similarity	NPC9303
0.7455	Intermediate Similarity	NPC475802
0.7455	Intermediate Similarity	NPC16313
0.7453	Intermediate Similarity	NPC40812
0.7451	Intermediate Similarity	NPC206001
0.7451	Intermediate Similarity	NPC218927
0.7436	Intermediate Similarity	NPC264954
0.7436	Intermediate Similarity	NPC236918
0.7436	Intermediate Similarity	NPC156745
0.7436	Intermediate Similarity	NPC61520
0.7434	Intermediate Similarity	NPC207689
0.7434	Intermediate Similarity	NPC188738
0.7431	Intermediate Similarity	NPC159533
0.7431	Intermediate Similarity	NPC475050
0.7429	Intermediate Similarity	NPC270013
0.7429	Intermediate Similarity	NPC14961
0.7417	Intermediate Similarity	NPC145238
0.7417	Intermediate Similarity	NPC172154
0.7417	Intermediate Similarity	NPC81736
0.7417	Intermediate Similarity	NPC8369
0.7417	Intermediate Similarity	NPC24651
0.7417	Intermediate Similarity	NPC470922
0.7414	Intermediate Similarity	NPC471146
0.7414	Intermediate Similarity	NPC243065
0.7414	Intermediate Similarity	NPC471145
0.7414	Intermediate Similarity	NPC23046
0.7414	Intermediate Similarity	NPC153651
0.7411	Intermediate Similarity	NPC475065
0.7407	Intermediate Similarity	NPC47880
0.7407	Intermediate Similarity	NPC474742
0.7407	Intermediate Similarity	NPC97435
0.74	Intermediate Similarity	NPC77971

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 NPC104161 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	198
0.1-0.2	1642
0.2-0.3	3678
0.3-0.4	2346
0.4-0.5	909
0.5-0.6	315
0.6-0.7	54
0.7-0.8	8
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
0.7565	Intermediate Similarity	NPD7115	Discovery
0.7379	Intermediate Similarity	NPD7838	Discovery
0.7308	Intermediate Similarity	NPD7983	Approved
0.7248	Intermediate Similarity	NPD5344	Discontinued
0.7238	Intermediate Similarity	NPD5778	Approved
0.7238	Intermediate Similarity	NPD5779	Approved
0.7227	Intermediate Similarity	NPD6319	Approved
0.7222	Intermediate Similarity	NPD4225	Approved
0.7212	Intermediate Similarity	NPD46	Approved
0.7212	Intermediate Similarity	NPD6698	Approved
0.7156	Intermediate Similarity	NPD6648	Approved
0.7043	Intermediate Similarity	NPD6371	Approved
0.6939	Remote Similarity	NPD4756	Discovery
0.693	Remote Similarity	NPD5697	Approved
0.693	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD8297	Approved
0.6909	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6885	Remote Similarity	NPD8516	Approved
0.6885	Remote Similarity	NPD8513	Phase 3
0.6885	Remote Similarity	NPD8515	Approved
0.6885	Remote Similarity	NPD8517	Approved
0.687	Remote Similarity	NPD6899	Approved
0.687	Remote Similarity	NPD6881	Approved
0.6864	Remote Similarity	NPD4632	Approved
0.6855	Remote Similarity	NPD7492	Approved
0.6838	Remote Similarity	NPD6650	Approved
0.6838	Remote Similarity	NPD6649	Approved
0.681	Remote Similarity	NPD6014	Approved
0.681	Remote Similarity	NPD6012	Approved
0.681	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.681	Remote Similarity	NPD6013	Approved
0.6803	Remote Similarity	NPD6054	Approved
0.68	Remote Similarity	NPD6616	Approved
0.6774	Remote Similarity	NPD8328	Phase 3
0.6752	Remote Similarity	NPD7290	Approved
0.6752	Remote Similarity	NPD4634	Approved
0.6752	Remote Similarity	NPD6883	Approved
0.6752	Remote Similarity	NPD7102	Approved
0.6748	Remote Similarity	NPD6015	Approved
0.6748	Remote Similarity	NPD6016	Approved
0.6746	Remote Similarity	NPD7078	Approved
0.6731	Remote Similarity	NPD1696	Phase 3
0.6724	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6724	Remote Similarity	NPD6011	Approved
0.6699	Remote Similarity	NPD6110	Phase 1
0.6697	Remote Similarity	NPD5282	Discontinued
0.6696	Remote Similarity	NPD6675	Approved
0.6696	Remote Similarity	NPD7128	Approved
0.6696	Remote Similarity	NPD6402	Approved
0.6696	Remote Similarity	NPD5739	Approved
0.6695	Remote Similarity	NPD6847	Approved
0.6695	Remote Similarity	NPD8130	Phase 1
0.6695	Remote Similarity	NPD6617	Approved
0.6695	Remote Similarity	NPD6869	Approved
0.6694	Remote Similarity	NPD6370	Approved
0.6694	Remote Similarity	NPD6009	Approved
0.6694	Remote Similarity	NPD5988	Approved
0.6693	Remote Similarity	NPD7736	Approved
0.6667	Remote Similarity	NPD6372	Approved
0.6667	Remote Similarity	NPD6373	Approved
0.664	Remote Similarity	NPD7604	Phase 2
0.6639	Remote Similarity	NPD6882	Approved
0.6638	Remote Similarity	NPD5701	Approved
0.6636	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6636	Remote Similarity	NPD6101	Approved
0.6614	Remote Similarity	NPD8074	Phase 3
0.6613	Remote Similarity	NPD5983	Phase 2
0.661	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6581	Remote Similarity	NPD7320	Approved
0.6579	Remote Similarity	NPD5211	Phase 2
0.6577	Remote Similarity	NPD7839	Suspended
0.6571	Remote Similarity	NPD5363	Approved
0.6555	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6532	Remote Similarity	NPD6059	Approved
0.6514	Remote Similarity	NPD6411	Approved
0.6486	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6484	Remote Similarity	NPD8293	Discontinued
0.6466	Remote Similarity	NPD5141	Approved
0.6423	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6422	Remote Similarity	NPD5785	Approved
0.641	Remote Similarity	NPD6008	Approved
0.6408	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6406	Remote Similarity	NPD6336	Discontinued
0.6404	Remote Similarity	NPD5286	Approved
0.6404	Remote Similarity	NPD7640	Approved
0.6404	Remote Similarity	NPD4696	Approved
0.6404	Remote Similarity	NPD5285	Approved
0.6404	Remote Similarity	NPD7639	Approved
0.6372	Remote Similarity	NPD6083	Phase 2
0.6372	Remote Similarity	NPD6084	Phase 2
0.6372	Remote Similarity	NPD7902	Approved
0.6364	Remote Similarity	NPD7637	Suspended
0.6356	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6341	Remote Similarity	NPD6274	Approved
0.6339	Remote Similarity	NPD5695	Phase 3
0.632	Remote Similarity	NPD7100	Approved
0.632	Remote Similarity	NPD7101	Approved
0.6316	Remote Similarity	NPD5696	Approved
0.6316	Remote Similarity	NPD7638	Approved
0.6303	Remote Similarity	NPD6686	Approved
0.6293	Remote Similarity	NPD5224	Approved
0.6293	Remote Similarity	NPD5225	Approved
0.6293	Remote Similarity	NPD5226	Approved
0.6293	Remote Similarity	NPD4633	Approved
0.629	Remote Similarity	NPD6317	Approved
0.6288	Remote Similarity	NPD7260	Phase 2
0.6286	Remote Similarity	NPD4269	Approved
0.6286	Remote Similarity	NPD5209	Approved
0.6286	Remote Similarity	NPD4270	Approved
0.6281	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6281	Remote Similarity	NPD7601	Clinical (unspecified phase)
0.6279	Remote Similarity	NPD8273	Phase 1
0.6262	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6262	Remote Similarity	NPD1694	Approved
0.625	Remote Similarity	NPD7748	Approved
0.625	Remote Similarity	NPD7642	Approved
0.625	Remote Similarity	NPD7829	Approved
0.625	Remote Similarity	NPD4252	Approved
0.625	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.625	Remote Similarity	NPD7830	Approved
0.624	Remote Similarity	NPD6335	Approved
0.624	Remote Similarity	NPD6313	Approved
0.624	Remote Similarity	NPD6314	Approved
0.6239	Remote Similarity	NPD5175	Approved
0.6239	Remote Similarity	NPD5174	Approved
0.6228	Remote Similarity	NPD4755	Approved
0.6226	Remote Similarity	NPD7154	Phase 3
0.622	Remote Similarity	NPD7503	Approved
0.6216	Remote Similarity	NPD7515	Phase 2
0.6207	Remote Similarity	NPD5223	Approved
0.6204	Remote Similarity	NPD5786	Approved
0.6204	Remote Similarity	NPD4249	Approved
0.619	Remote Similarity	NPD5369	Approved
0.6176	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6161	Remote Similarity	NPD6399	Phase 3
0.6147	Remote Similarity	NPD4251	Approved
0.6147	Remote Similarity	NPD4250	Approved
0.614	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.614	Remote Similarity	NPD5221	Approved
0.614	Remote Similarity	NPD5222	Approved
0.6136	Remote Similarity	NPD7319	Approved
0.6121	Remote Similarity	NPD4700	Approved
0.6116	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6111	Remote Similarity	NPD7641	Discontinued
0.6106	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6106	Remote Similarity	NPD7900	Approved
0.6098	Remote Similarity	NPD6053	Discontinued
0.6095	Remote Similarity	NPD4820	Approved
0.6095	Remote Similarity	NPD4822	Approved
0.6095	Remote Similarity	NPD4819	Approved
0.6095	Remote Similarity	NPD4821	Approved
0.6094	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6094	Remote Similarity	NPD6921	Approved
0.6087	Remote Similarity	NPD5173	Approved
0.6083	Remote Similarity	NPD6412	Phase 2
0.608	Remote Similarity	NPD6868	Approved
0.6077	Remote Similarity	NPD8340	Approved
0.6077	Remote Similarity	NPD8299	Approved
0.6077	Remote Similarity	NPD8341	Approved
0.6077	Remote Similarity	NPD8342	Approved
0.6071	Remote Similarity	NPD5284	Approved
0.6071	Remote Similarity	NPD5281	Approved
0.6071	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.6071	Remote Similarity	NPD5694	Approved
0.6061	Remote Similarity	NPD6033	Approved
0.6058	Remote Similarity	NPD4268	Approved
0.6058	Remote Similarity	NPD4271	Approved
0.6055	Remote Similarity	NPD3618	Phase 1
0.6053	Remote Similarity	NPD5210	Approved
0.6053	Remote Similarity	NPD4629	Approved
0.6036	Remote Similarity	NPD5370	Suspended
0.6036	Remote Similarity	NPD1695	Approved
0.6033	Remote Similarity	NPD4729	Approved
0.6033	Remote Similarity	NPD4730	Approved
0.6032	Remote Similarity	NPD7500	Approved
0.6031	Remote Similarity	NPD7507	Approved
0.602	Remote Similarity	NPD4247	Clinical (unspecified phase)
0.6	Remote Similarity	NPD3573	Approved
0.6	Remote Similarity	NPD4697	Phase 3
0.5982	Remote Similarity	NPD5692	Phase 3
0.597	Remote Similarity	NPD5956	Approved
0.5969	Remote Similarity	NPD6909	Approved
0.5969	Remote Similarity	NPD6908	Approved
0.5952	Remote Similarity	NPD2629	Approved
0.5946	Remote Similarity	NPD6672	Approved
0.5946	Remote Similarity	NPD5737	Approved
0.5938	Remote Similarity	NPD4522	Approved
0.5935	Remote Similarity	NPD5249	Phase 3
0.5935	Remote Similarity	NPD5247	Approved
0.5935	Remote Similarity	NPD5251	Approved
0.5935	Remote Similarity	NPD5248	Approved
0.5935	Remote Similarity	NPD5250	Approved
0.5929	Remote Similarity	NPD6079	Approved
0.5929	Remote Similarity	NPD6050	Approved
0.5926	Remote Similarity	NPD5362	Discontinued
0.5918	Remote Similarity	NPD3704	Approved
0.5909	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.5909	Remote Similarity	NPD8451	Approved
0.5909	Remote Similarity	NPD5279	Phase 3
0.5902	Remote Similarity	NPD5128	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