NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	278.15
Volume:	286.874
LogP:	2.877
LogD:	2.543
LogS:	-4.191
# Rotatable Bonds:	2
TPSA:	59.06
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.622
Synthetic Accessibility Score:	4.72
Fsp3:	0.688
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:	-4.582
MDCK Permeability:	2.5078388716792688e-05
Pgp-inhibitor:	0.123
Pgp-substrate:	0.013
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.058
30% Bioavailability (F30%):	0.347

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.773
Plasma Protein Binding (PPB):	81.12100982666016%
Volume Distribution (VD):	1.388
Pgp-substrate:	20.272451400756836%

ADMET: Metabolism

CYP1A2-inhibitor:	0.033
CYP1A2-substrate:	0.292
CYP2C19-inhibitor:	0.176
CYP2C19-substrate:	0.769
CYP2C9-inhibitor:	0.049
CYP2C9-substrate:	0.056
CYP2D6-inhibitor:	0.012
CYP2D6-substrate:	0.093
CYP3A4-inhibitor:	0.077
CYP3A4-substrate:	0.366

ADMET: Excretion

Clearance (CL):	15.998
Half-life (T1/2):	0.15

ADMET: Toxicity

hERG Blockers:	0.009
Human Hepatotoxicity (H-HT):	0.565
Drug-inuced Liver Injury (DILI):	0.234
AMES Toxicity:	0.091
Rat Oral Acute Toxicity:	0.959
Maximum Recommended Daily Dose:	0.078
Skin Sensitization:	0.541
Carcinogencity:	0.929
Eye Corrosion:	0.009
Eye Irritation:	0.099
Respiratory Toxicity:	0.964

Download Data

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

Natural Product: NPC306908

Natural Product ID:	NPC306908
*Common Name:**	Pestaloficiol F
IUPAC Name:	(1aS,2S,7bS)-2-hydroxy-6,6-dimethyl-7b-(3-methylbut-2-enyl)-1a,2,3,5-tetrahydrooxireno[2,3-h]chromen-4-one
Synonyms:	Pestaloficiol F
Standard InCHIKey:	DWRYREFBMYRRST-HZUKXOBISA-N
Standard InCHI:	InChI=1S/C16H22O4/c1-9(2)5-6-16-13-10(7-11(17)14(16)20-16)12(18)8-15(3,4)19-13/h5,11,14,17H,6-8H2,1-4H3/t11-,14-,16+/m0/s1
SMILES:	CC(=CC[C@@]12C3=C(C[C@@H]([C@@H]1O2)O)C(=O)CC(C)(C)O3)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1078031
PubChem CID:	44254170
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000086] Pyrans [CHEMONTID:0000481] Pyranones and derivatives [CHEMONTID:0001211] Dihydropyranones

*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
NPO22690	Pestalotiopsis fici	Species	Sporocadaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18468908]
NPO22690	Pestalotiopsis fici	Species	Sporocadaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19101157]
NPO22690	Pestalotiopsis fici	Species	Sporocadaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19618920]
NPO22690	Pestalotiopsis fici	Species	Sporocadaceae	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
EC50	1
IC50	2

Activity Type	# Activity
Cell Line	2
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT165	Cell Line	HeLa	Homo sapiens	IC50	>	143900.0	nM	PMID[530072]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	>	143900.0	nM	PMID[530072]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	EC50	>	100000.0	nM	PMID[530072]

☑ 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 NPC306908 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	218
0.1-0.2	1353
0.2-0.3	4659
0.3-0.4	8820
0.4-0.5	16533
0.5-0.6	7590
0.6-0.7	3070
0.7-0.8	432
0.8-0.85	19
0.85-0.9	2
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9158	High Similarity	NPC35717
0.9022	High Similarity	NPC469464
0.8261	Intermediate Similarity	NPC185256
0.8229	Intermediate Similarity	NPC265856
0.81	Intermediate Similarity	NPC20066
0.81	Intermediate Similarity	NPC473574
0.81	Intermediate Similarity	NPC20078
0.8039	Intermediate Similarity	NPC181645
0.7944	Intermediate Similarity	NPC99760
0.7885	Intermediate Similarity	NPC473624
0.7857	Intermediate Similarity	NPC166554
0.7857	Intermediate Similarity	NPC477684
0.7835	Intermediate Similarity	NPC472008
0.78	Intermediate Similarity	NPC477241
0.7778	Intermediate Similarity	NPC475441
0.7778	Intermediate Similarity	NPC146852
0.7745	Intermediate Similarity	NPC239895
0.7736	Intermediate Similarity	NPC469852
0.7732	Intermediate Similarity	NPC472007
0.7708	Intermediate Similarity	NPC68303
0.7708	Intermediate Similarity	NPC307126
0.77	Intermediate Similarity	NPC61275
0.7685	Intermediate Similarity	NPC101018
0.7685	Intermediate Similarity	NPC471400
0.7679	Intermediate Similarity	NPC478204
0.7679	Intermediate Similarity	NPC53396
0.7679	Intermediate Similarity	NPC98249
0.7679	Intermediate Similarity	NPC469684
0.767	Intermediate Similarity	NPC300584
0.7664	Intermediate Similarity	NPC469853
0.7629	Intermediate Similarity	NPC472009
0.7619	Intermediate Similarity	NPC39996
0.7611	Intermediate Similarity	NPC478206
0.7611	Intermediate Similarity	NPC478205
0.7611	Intermediate Similarity	NPC284707
0.7611	Intermediate Similarity	NPC108581
0.7549	Intermediate Similarity	NPC91408
0.7545	Intermediate Similarity	NPC317107
0.7524	Intermediate Similarity	NPC224172
0.7524	Intermediate Similarity	NPC207885
0.7524	Intermediate Similarity	NPC471401
0.7522	Intermediate Similarity	NPC58662
0.75	Intermediate Similarity	NPC475284
0.75	Intermediate Similarity	NPC474716
0.75	Intermediate Similarity	NPC80650
0.75	Intermediate Similarity	NPC281608
0.75	Intermediate Similarity	NPC471399
0.7479	Intermediate Similarity	NPC477712
0.7479	Intermediate Similarity	NPC477713
0.7477	Intermediate Similarity	NPC317687
0.7476	Intermediate Similarity	NPC473859
0.7476	Intermediate Similarity	NPC279722
0.7475	Intermediate Similarity	NPC87189
0.7475	Intermediate Similarity	NPC228415
0.7458	Intermediate Similarity	NPC293112
0.7449	Intermediate Similarity	NPC196381
0.7436	Intermediate Similarity	NPC11895
0.7431	Intermediate Similarity	NPC327106
0.7429	Intermediate Similarity	NPC288876
0.7426	Intermediate Similarity	NPC476705
0.7411	Intermediate Similarity	NPC478212
0.7404	Intermediate Similarity	NPC236176
0.7404	Intermediate Similarity	NPC266842
0.7404	Intermediate Similarity	NPC134454
0.7404	Intermediate Similarity	NPC17326
0.7387	Intermediate Similarity	NPC476023
0.7387	Intermediate Similarity	NPC469655
0.7387	Intermediate Similarity	NPC469656
0.7387	Intermediate Similarity	NPC474846
0.7379	Intermediate Similarity	NPC475659
0.7379	Intermediate Similarity	NPC316215
0.7379	Intermediate Similarity	NPC270013
0.7379	Intermediate Similarity	NPC14961
0.7374	Intermediate Similarity	NPC471738
0.7374	Intermediate Similarity	NPC23622
0.7373	Intermediate Similarity	NPC172154
0.7373	Intermediate Similarity	NPC81736
0.7368	Intermediate Similarity	NPC91332
0.7368	Intermediate Similarity	NPC162741
0.7364	Intermediate Similarity	NPC87335
0.7364	Intermediate Similarity	NPC77089
0.7358	Intermediate Similarity	NPC46998
0.7358	Intermediate Similarity	NPC110443
0.7358	Intermediate Similarity	NPC112613
0.7358	Intermediate Similarity	NPC185141
0.7358	Intermediate Similarity	NPC133907
0.7358	Intermediate Similarity	NPC469851
0.7358	Intermediate Similarity	NPC128733
0.7353	Intermediate Similarity	NPC212486
0.735	Intermediate Similarity	NPC170538
0.7347	Intermediate Similarity	NPC187529
0.7347	Intermediate Similarity	NPC307112
0.7345	Intermediate Similarity	NPC238667
0.7339	Intermediate Similarity	NPC266514
0.7333	Intermediate Similarity	NPC83895
0.7333	Intermediate Similarity	NPC187761
0.7327	Intermediate Similarity	NPC131864
0.732	Intermediate Similarity	NPC477784
0.732	Intermediate Similarity	NPC477785
0.732	Intermediate Similarity	NPC477786
0.7315	Intermediate Similarity	NPC474741
0.7311	Intermediate Similarity	NPC473635
0.7308	Intermediate Similarity	NPC472733
0.7308	Intermediate Similarity	NPC21302
0.7308	Intermediate Similarity	NPC11396
0.7308	Intermediate Similarity	NPC472734
0.7308	Intermediate Similarity	NPC93271
0.7308	Intermediate Similarity	NPC135576
0.7304	Intermediate Similarity	NPC50774
0.7304	Intermediate Similarity	NPC709
0.7304	Intermediate Similarity	NPC251310
0.7304	Intermediate Similarity	NPC186525
0.73	Intermediate Similarity	NPC476706
0.73	Intermediate Similarity	NPC476707
0.729	Intermediate Similarity	NPC478176
0.7288	Intermediate Similarity	NPC473802
0.7288	Intermediate Similarity	NPC469789
0.7282	Intermediate Similarity	NPC71589
0.7282	Intermediate Similarity	NPC474035
0.7282	Intermediate Similarity	NPC81386
0.7273	Intermediate Similarity	NPC322903
0.7273	Intermediate Similarity	NPC473807
0.7264	Intermediate Similarity	NPC469551
0.7257	Intermediate Similarity	NPC475966
0.7257	Intermediate Similarity	NPC477266
0.7255	Intermediate Similarity	NPC327760
0.7255	Intermediate Similarity	NPC472010
0.7248	Intermediate Similarity	NPC471332
0.7248	Intermediate Similarity	NPC471333
0.7245	Intermediate Similarity	NPC243618
0.7245	Intermediate Similarity	NPC72464
0.7245	Intermediate Similarity	NPC469809
0.7245	Intermediate Similarity	NPC70424
0.7241	Intermediate Similarity	NPC476107
0.7238	Intermediate Similarity	NPC471694
0.7238	Intermediate Similarity	NPC472731
0.7238	Intermediate Similarity	NPC472732
0.7238	Intermediate Similarity	NPC40812
0.7232	Intermediate Similarity	NPC474229
0.7227	Intermediate Similarity	NPC24651
0.7227	Intermediate Similarity	NPC473709
0.7227	Intermediate Similarity	NPC473919
0.7222	Intermediate Similarity	NPC118902
0.7222	Intermediate Similarity	NPC469980
0.7222	Intermediate Similarity	NPC104161
0.7222	Intermediate Similarity	NPC475945
0.7222	Intermediate Similarity	NPC123505
0.7222	Intermediate Similarity	NPC475871
0.7217	Intermediate Similarity	NPC477116
0.7217	Intermediate Similarity	NPC470492
0.7217	Intermediate Similarity	NPC312824
0.7217	Intermediate Similarity	NPC470493
0.7217	Intermediate Similarity	NPC27999
0.7217	Intermediate Similarity	NPC474518
0.7217	Intermediate Similarity	NPC167606
0.7217	Intermediate Similarity	NPC140055
0.7217	Intermediate Similarity	NPC13713
0.7217	Intermediate Similarity	NPC286528
0.7217	Intermediate Similarity	NPC20302
0.7217	Intermediate Similarity	NPC183580
0.7212	Intermediate Similarity	NPC227494
0.7212	Intermediate Similarity	NPC471698
0.7212	Intermediate Similarity	NPC279313
0.7207	Intermediate Similarity	NPC38154
0.7207	Intermediate Similarity	NPC469370
0.7203	Intermediate Similarity	NPC312833
0.72	Intermediate Similarity	NPC103743
0.72	Intermediate Similarity	NPC476079
0.72	Intermediate Similarity	NPC113370
0.72	Intermediate Similarity	NPC300779
0.7196	Intermediate Similarity	NPC474339
0.7196	Intermediate Similarity	NPC476270
0.7196	Intermediate Similarity	NPC472637
0.7196	Intermediate Similarity	NPC164598
0.7196	Intermediate Similarity	NPC201718
0.7196	Intermediate Similarity	NPC472753
0.7196	Intermediate Similarity	NPC9878
0.7193	Intermediate Similarity	NPC284915
0.7193	Intermediate Similarity	NPC247069
0.7188	Intermediate Similarity	NPC470945
0.7188	Intermediate Similarity	NPC470947
0.7188	Intermediate Similarity	NPC470946
0.7184	Intermediate Similarity	NPC162205
0.7184	Intermediate Similarity	NPC469692
0.7184	Intermediate Similarity	NPC282644
0.7184	Intermediate Similarity	NPC469645
0.7184	Intermediate Similarity	NPC273579
0.7184	Intermediate Similarity	NPC295204
0.7184	Intermediate Similarity	NPC475912
0.7184	Intermediate Similarity	NPC288240
0.7184	Intermediate Similarity	NPC29798
0.7182	Intermediate Similarity	NPC477513
0.7182	Intermediate Similarity	NPC469558
0.7179	Intermediate Similarity	NPC154491
0.7179	Intermediate Similarity	NPC474370
0.7179	Intermediate Similarity	NPC251226
0.7179	Intermediate Similarity	NPC268530
0.717	Intermediate Similarity	NPC153776
0.717	Intermediate Similarity	NPC473326
0.717	Intermediate Similarity	NPC472730

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 NPC306908 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	201
0.1-0.2	1819
0.2-0.3	3704
0.3-0.4	2287
0.4-0.5	830
0.5-0.6	264
0.6-0.7	43
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
0.7327	Intermediate Similarity	NPD6698	Approved
0.7327	Intermediate Similarity	NPD46	Approved
0.7217	Intermediate Similarity	NPD7115	Discovery
0.6903	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6881	Remote Similarity	NPD5344	Discontinued
0.6852	Remote Similarity	NPD4225	Approved
0.6762	Remote Similarity	NPD7983	Approved
0.6729	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6698	Remote Similarity	NPD5779	Approved
0.6698	Remote Similarity	NPD5778	Approved
0.6696	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6696	Remote Similarity	NPD6371	Approved
0.6694	Remote Similarity	NPD8513	Phase 3
0.6667	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6636	Remote Similarity	NPD5282	Discontinued
0.6634	Remote Similarity	NPD6110	Phase 1
0.6581	Remote Similarity	NPD6053	Discontinued
0.6571	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6571	Remote Similarity	NPD6101	Approved
0.6557	Remote Similarity	NPD8517	Approved
0.6557	Remote Similarity	NPD8515	Approved
0.6557	Remote Similarity	NPD8516	Approved
0.6522	Remote Similarity	NPD7331	Phase 2
0.6509	Remote Similarity	NPD7838	Discovery
0.6505	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6486	Remote Similarity	NPD6648	Approved
0.6449	Remote Similarity	NPD6411	Approved
0.6435	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6435	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6355	Remote Similarity	NPD5785	Approved
0.632	Remote Similarity	NPD7642	Approved
0.6311	Remote Similarity	NPD7154	Phase 3
0.6306	Remote Similarity	NPD4755	Approved
0.6299	Remote Similarity	NPD8074	Phase 3
0.6286	Remote Similarity	NPD5786	Approved
0.6271	Remote Similarity	NPD4634	Approved
0.625	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6228	Remote Similarity	NPD5211	Phase 2
0.6218	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6214	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.621	Remote Similarity	NPD6319	Approved
0.6207	Remote Similarity	NPD6675	Approved
0.6207	Remote Similarity	NPD7128	Approved
0.6207	Remote Similarity	NPD5739	Approved
0.6207	Remote Similarity	NPD6402	Approved
0.6202	Remote Similarity	NPD7319	Approved
0.6195	Remote Similarity	NPD5285	Approved
0.6195	Remote Similarity	NPD4696	Approved
0.6195	Remote Similarity	NPD5286	Approved
0.6195	Remote Similarity	NPD4700	Approved
0.619	Remote Similarity	NPD7829	Approved
0.619	Remote Similarity	NPD7830	Approved
0.619	Remote Similarity	NPD5363	Approved
0.6186	Remote Similarity	NPD6372	Approved
0.6186	Remote Similarity	NPD6373	Approved
0.6176	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.617	Remote Similarity	NPD3704	Approved
0.6167	Remote Similarity	NPD8297	Approved
0.6154	Remote Similarity	NPD5701	Approved
0.6154	Remote Similarity	NPD5697	Approved
0.6132	Remote Similarity	NPD3618	Phase 1
0.6121	Remote Similarity	NPD5141	Approved
0.6117	Remote Similarity	NPD5369	Approved
0.6111	Remote Similarity	NPD5328	Approved
0.6102	Remote Similarity	NPD6881	Approved
0.6102	Remote Similarity	NPD6899	Approved
0.6102	Remote Similarity	NPD6686	Approved
0.6102	Remote Similarity	NPD7320	Approved
0.6095	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6087	Remote Similarity	NPD5225	Approved
0.6087	Remote Similarity	NPD5224	Approved
0.6087	Remote Similarity	NPD4633	Approved
0.6087	Remote Similarity	NPD5226	Approved
0.6083	Remote Similarity	NPD6649	Approved
0.6083	Remote Similarity	NPD6650	Approved
0.608	Remote Similarity	NPD6059	Approved
0.608	Remote Similarity	NPD6054	Approved
0.6071	Remote Similarity	NPD7839	Suspended
0.6071	Remote Similarity	NPD4697	Phase 3
0.6068	Remote Similarity	NPD6008	Approved
0.6064	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6064	Remote Similarity	NPD7341	Phase 2
0.6063	Remote Similarity	NPD8328	Phase 3
0.6058	Remote Similarity	NPD6435	Approved
0.6058	Remote Similarity	NPD4269	Approved
0.6058	Remote Similarity	NPD4270	Approved
0.605	Remote Similarity	NPD6014	Approved
0.605	Remote Similarity	NPD6012	Approved
0.605	Remote Similarity	NPD6013	Approved
0.604	Remote Similarity	NPD4756	Discovery
0.6038	Remote Similarity	NPD1694	Approved
0.6038	Remote Similarity	NPD1696	Phase 3
0.6034	Remote Similarity	NPD5175	Approved
0.6034	Remote Similarity	NPD5174	Approved
0.6032	Remote Similarity	NPD6921	Approved
0.6032	Remote Similarity	NPD6016	Approved
0.6032	Remote Similarity	NPD6015	Approved
0.6018	Remote Similarity	NPD7902	Approved
0.6	Remote Similarity	NPD7102	Approved
0.6	Remote Similarity	NPD6079	Approved
0.6	Remote Similarity	NPD5223	Approved
0.6	Remote Similarity	NPD7290	Approved
0.6	Remote Similarity	NPD6883	Approved
0.5984	Remote Similarity	NPD4632	Approved
0.5984	Remote Similarity	NPD5988	Approved
0.5984	Remote Similarity	NPD6370	Approved
0.5969	Remote Similarity	NPD7507	Approved
0.5966	Remote Similarity	NPD6011	Approved
0.595	Remote Similarity	NPD8130	Phase 1
0.595	Remote Similarity	NPD6869	Approved
0.595	Remote Similarity	NPD6617	Approved
0.595	Remote Similarity	NPD6847	Approved
0.5946	Remote Similarity	NPD6399	Phase 3
0.5946	Remote Similarity	NPD4202	Approved
0.5932	Remote Similarity	NPD4768	Approved
0.5932	Remote Similarity	NPD4767	Approved
0.5929	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.5929	Remote Similarity	NPD5222	Approved
0.5929	Remote Similarity	NPD5221	Approved
0.5905	Remote Similarity	NPD3667	Approved
0.5902	Remote Similarity	NPD6882	Approved
0.5897	Remote Similarity	NPD4754	Approved
0.5893	Remote Similarity	NPD7748	Approved
0.5891	Remote Similarity	NPD7492	Approved
0.5882	Remote Similarity	NPD6412	Phase 2
0.5877	Remote Similarity	NPD5173	Approved
0.5865	Remote Similarity	NPD4695	Discontinued
0.5865	Remote Similarity	NPD4252	Approved
0.5865	Remote Similarity	NPD5368	Approved
0.5862	Remote Similarity	NPD4159	Approved
0.5856	Remote Similarity	NPD7515	Phase 2
0.5851	Remote Similarity	NPD2664	Clinical (unspecified phase)
0.5846	Remote Similarity	NPD6616	Approved
0.5846	Remote Similarity	NPD8451	Approved
0.5833	Remote Similarity	NPD4730	Approved
0.5833	Remote Similarity	NPD4729	Approved
0.5833	Remote Similarity	NPD5128	Approved
0.5833	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.5826	Remote Similarity	NPD7638	Approved
0.582	Remote Similarity	NPD7116	Clinical (unspecified phase)
0.582	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.5818	Remote Similarity	NPD4753	Phase 2
0.5818	Remote Similarity	NPD1695	Approved
0.5802	Remote Similarity	NPD7078	Approved
0.5802	Remote Similarity	NPD8293	Discontinued
0.5802	Remote Similarity	NPD8448	Approved
0.5794	Remote Similarity	NPD3133	Approved
0.5794	Remote Similarity	NPD3665	Phase 1
0.5794	Remote Similarity	NPD4786	Approved
0.5794	Remote Similarity	NPD3666	Approved
0.5781	Remote Similarity	NPD8444	Approved
0.578	Remote Similarity	NPD7524	Approved
0.5776	Remote Similarity	NPD7639	Approved
0.5776	Remote Similarity	NPD7640	Approved
0.5766	Remote Similarity	NPD3168	Discontinued
0.576	Remote Similarity	NPD6274	Approved
0.5758	Remote Similarity	NPD7736	Approved
0.5755	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.5755	Remote Similarity	NPD5209	Approved
0.5752	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.5752	Remote Similarity	NPD7900	Approved
0.5748	Remote Similarity	NPD7516	Approved
0.5741	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.5739	Remote Similarity	NPD6083	Phase 2
0.5739	Remote Similarity	NPD6084	Phase 2
0.5738	Remote Similarity	NPD5248	Approved
0.5738	Remote Similarity	NPD5250	Approved
0.5738	Remote Similarity	NPD5247	Approved
0.5738	Remote Similarity	NPD5251	Approved
0.5738	Remote Similarity	NPD5249	Phase 3
0.5736	Remote Similarity	NPD8080	Discontinued
0.5735	Remote Similarity	NPD8415	Approved
0.5725	Remote Similarity	NPD8273	Phase 1
0.5714	Remote Similarity	NPD4819	Approved
0.5714	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD6009	Approved
0.5714	Remote Similarity	NPD4820	Approved
0.5714	Remote Similarity	NPD4822	Approved
0.5714	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD4821	Approved
0.5714	Remote Similarity	NPD7637	Suspended
0.5714	Remote Similarity	NPD7500	Approved
0.5703	Remote Similarity	NPD7299	Clinical (unspecified phase)
0.5702	Remote Similarity	NPD4629	Approved
0.5702	Remote Similarity	NPD5695	Phase 3
0.5702	Remote Similarity	NPD5210	Approved
0.5701	Remote Similarity	NPD5362	Discontinued
0.5693	Remote Similarity	NPD8387	Clinical (unspecified phase)
0.5692	Remote Similarity	NPD7604	Phase 2
0.5691	Remote Similarity	NPD5215	Approved
0.5691	Remote Similarity	NPD5216	Approved
0.5691	Remote Similarity	NPD5217	Approved
0.569	Remote Similarity	NPD5696	Approved
0.5688	Remote Similarity	NPD4249	Approved
0.5688	Remote Similarity	NPD5279	Phase 3
0.5686	Remote Similarity	NPD8039	Approved
0.5672	Remote Similarity	NPD8392	Approved
0.5672	Remote Similarity	NPD8390	Approved
0.5672	Remote Similarity	NPD8391	Approved
0.567	Remote Similarity	NPD6108	Clinical (unspecified phase)

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data