NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	262.16
Volume:	284.004
LogP:	3.538
LogD:	2.978
LogS:	-4.101
# Rotatable Bonds:	3
TPSA:	49.83
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.483
Synthetic Accessibility Score:	4.678
Fsp3:	0.562
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:	-4.483
MDCK Permeability:	2.687656342459377e-05
Pgp-inhibitor:	0.903
Pgp-substrate:	0.309
Human Intestinal Absorption (HIA):	0.009
20% Bioavailability (F20%):	0.037
30% Bioavailability (F30%):	0.014

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.873
Plasma Protein Binding (PPB):	83.91490936279297%
Volume Distribution (VD):	2.104
Pgp-substrate:	16.1196231842041%

ADMET: Metabolism

CYP1A2-inhibitor:	0.244
CYP1A2-substrate:	0.435
CYP2C19-inhibitor:	0.298
CYP2C19-substrate:	0.86
CYP2C9-inhibitor:	0.209
CYP2C9-substrate:	0.091
CYP2D6-inhibitor:	0.018
CYP2D6-substrate:	0.279
CYP3A4-inhibitor:	0.049
CYP3A4-substrate:	0.364

ADMET: Excretion

Clearance (CL):	10.836
Half-life (T1/2):	0.334

ADMET: Toxicity

hERG Blockers:	0.017
Human Hepatotoxicity (H-HT):	0.78
Drug-inuced Liver Injury (DILI):	0.056
AMES Toxicity:	0.593
Rat Oral Acute Toxicity:	0.907
Maximum Recommended Daily Dose:	0.191
Skin Sensitization:	0.917
Carcinogencity:	0.679
Eye Corrosion:	0.145
Eye Irritation:	0.785
Respiratory Toxicity:	0.92

Download Data

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

Natural Product: NPC279722

Natural Product ID:	NPC279722
*Common Name:**	Pestalofone A
IUPAC Name:	(1S,2S,4E,6S)-2-hydroxy-6-(3-methylbut-2-enyl)-4-(3-methylbut-2-enylidene)-7-oxabicyclo[4.1.0]heptan-5-one
Synonyms:
Standard InCHIKey:	XPTXPZUFXASXPQ-KHCQGZIYSA-N
Standard InCHI:	InChI=1S/C16H22O3/c1-10(2)5-6-12-9-13(17)15-16(19-15,14(12)18)8-7-11(3)4/h5-7,13,15,17H,8-9H2,1-4H3/b12-6+/t13-,15-,16+/m0/s1
SMILES:	CC(=C/C=C/1C[C@H](O)[C@H]2[C@](C1=O)(CC=C(C)C)O2)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL522607
PubChem CID:	42609854
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001729] Oxepanes

*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
Others	1

Activity Type	# Activity
Cell Line	1
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1452	Cell Line	C8166	Homo sapiens	CC50	>	200000.0	nM	PMID[512137]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	EC50	=	90400.0	nM	PMID[512137]

☑ 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 NPC279722 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	1375
0.2-0.3	4994
0.3-0.4	8758
0.4-0.5	16357
0.5-0.6	8389
0.6-0.7	2362
0.7-0.8	240
0.8-0.85	3
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8646	High Similarity	NPC236176
0.8544	High Similarity	NPC476023
0.8222	Intermediate Similarity	NPC67254
0.8039	Intermediate Similarity	NPC469980
0.8039	Intermediate Similarity	NPC104161
0.8039	Intermediate Similarity	NPC118902
0.7981	Intermediate Similarity	NPC266514
0.7979	Intermediate Similarity	NPC262026
0.7963	Intermediate Similarity	NPC80650
0.7941	Intermediate Similarity	NPC39996
0.7835	Intermediate Similarity	NPC477684
0.781	Intermediate Similarity	NPC474716
0.7767	Intermediate Similarity	NPC478176
0.7706	Intermediate Similarity	NPC477266
0.7685	Intermediate Similarity	NPC474229
0.7677	Intermediate Similarity	NPC61275
0.767	Intermediate Similarity	NPC476270
0.7629	Intermediate Similarity	NPC476706
0.7629	Intermediate Similarity	NPC476707
0.7604	Intermediate Similarity	NPC196381
0.7586	Intermediate Similarity	NPC471939
0.7576	Intermediate Similarity	NPC146852
0.7573	Intermediate Similarity	NPC469551
0.7521	Intermediate Similarity	NPC471940
0.75	Intermediate Similarity	NPC38154
0.75	Intermediate Similarity	NPC474339
0.75	Intermediate Similarity	NPC87335
0.75	Intermediate Similarity	NPC477116
0.75	Intermediate Similarity	NPC164598
0.75	Intermediate Similarity	NPC27999
0.75	Intermediate Similarity	NPC201718
0.7477	Intermediate Similarity	NPC477513
0.7477	Intermediate Similarity	NPC469558
0.7476	Intermediate Similarity	NPC306908
0.7456	Intermediate Similarity	NPC478051
0.7453	Intermediate Similarity	NPC474741
0.7449	Intermediate Similarity	NPC476708
0.7436	Intermediate Similarity	NPC225049
0.7434	Intermediate Similarity	NPC17772
0.7431	Intermediate Similarity	NPC89408
0.7429	Intermediate Similarity	NPC474747
0.7414	Intermediate Similarity	NPC473802
0.7411	Intermediate Similarity	NPC207217
0.7404	Intermediate Similarity	NPC475949
0.74	Intermediate Similarity	NPC476705
0.7396	Intermediate Similarity	NPC469809
0.7396	Intermediate Similarity	NPC136114
0.7391	Intermediate Similarity	NPC102822
0.7391	Intermediate Similarity	NPC477046
0.7387	Intermediate Similarity	NPC7921
0.7387	Intermediate Similarity	NPC208998
0.7383	Intermediate Similarity	NPC128828
0.7368	Intermediate Similarity	NPC470777
0.7364	Intermediate Similarity	NPC317107
0.7364	Intermediate Similarity	NPC146945
0.7364	Intermediate Similarity	NPC171888
0.7358	Intermediate Similarity	NPC320294
0.7358	Intermediate Similarity	NPC475871
0.7358	Intermediate Similarity	NPC475945
0.735	Intermediate Similarity	NPC473919
0.735	Intermediate Similarity	NPC473709
0.7345	Intermediate Similarity	NPC53396
0.7345	Intermediate Similarity	NPC122033
0.7345	Intermediate Similarity	NPC98249
0.7345	Intermediate Similarity	NPC474654
0.7345	Intermediate Similarity	NPC97908
0.7345	Intermediate Similarity	NPC287343
0.7345	Intermediate Similarity	NPC470854
0.734	Intermediate Similarity	NPC472948
0.7333	Intermediate Similarity	NPC475606
0.7333	Intermediate Similarity	NPC47880
0.7333	Intermediate Similarity	NPC251564
0.7333	Intermediate Similarity	NPC475314
0.7333	Intermediate Similarity	NPC112613
0.7333	Intermediate Similarity	NPC477189
0.7333	Intermediate Similarity	NPC474742
0.7327	Intermediate Similarity	NPC212486
0.732	Intermediate Similarity	NPC187529
0.732	Intermediate Similarity	NPC79573
0.7308	Intermediate Similarity	NPC471144
0.7308	Intermediate Similarity	NPC161855
0.7308	Intermediate Similarity	NPC300584
0.73	Intermediate Similarity	NPC65359
0.73	Intermediate Similarity	NPC469464
0.7297	Intermediate Similarity	NPC317687
0.7288	Intermediate Similarity	NPC217901
0.7282	Intermediate Similarity	NPC94337
0.7282	Intermediate Similarity	NPC473291
0.7281	Intermediate Similarity	NPC284707
0.7281	Intermediate Similarity	NPC251310
0.7273	Intermediate Similarity	NPC210005
0.7273	Intermediate Similarity	NPC201046
0.7273	Intermediate Similarity	NPC474508
0.7273	Intermediate Similarity	NPC476704
0.7273	Intermediate Similarity	NPC473485
0.7264	Intermediate Similarity	NPC471148
0.7264	Intermediate Similarity	NPC149371
0.7263	Intermediate Similarity	NPC286229
0.7257	Intermediate Similarity	NPC477509
0.7257	Intermediate Similarity	NPC328374
0.7257	Intermediate Similarity	NPC96312
0.7257	Intermediate Similarity	NPC270478
0.7257	Intermediate Similarity	NPC251236
0.7257	Intermediate Similarity	NPC40632
0.7248	Intermediate Similarity	NPC102843
0.7248	Intermediate Similarity	NPC29827
0.7241	Intermediate Similarity	NPC472401
0.7238	Intermediate Similarity	NPC324667
0.7238	Intermediate Similarity	NPC475053
0.7238	Intermediate Similarity	NPC288876
0.7232	Intermediate Similarity	NPC49451
0.7232	Intermediate Similarity	NPC198539
0.7228	Intermediate Similarity	NPC142838
0.7228	Intermediate Similarity	NPC469627
0.7228	Intermediate Similarity	NPC475441
0.7227	Intermediate Similarity	NPC475273
0.7227	Intermediate Similarity	NPC168849
0.7222	Intermediate Similarity	NPC474101
0.7212	Intermediate Similarity	NPC473574
0.7212	Intermediate Similarity	NPC20066
0.7212	Intermediate Similarity	NPC20078
0.7207	Intermediate Similarity	NPC207689
0.7203	Intermediate Similarity	NPC24651
0.7196	Intermediate Similarity	NPC472755
0.7196	Intermediate Similarity	NPC475873
0.7193	Intermediate Similarity	NPC476713
0.7193	Intermediate Similarity	NPC474518
0.7193	Intermediate Similarity	NPC476712
0.7193	Intermediate Similarity	NPC478204
0.7193	Intermediate Similarity	NPC156252
0.7188	Intermediate Similarity	NPC253364
0.7184	Intermediate Similarity	NPC14961
0.7184	Intermediate Similarity	NPC270013
0.7182	Intermediate Similarity	NPC471400
0.7182	Intermediate Similarity	NPC77089
0.7179	Intermediate Similarity	NPC19464
0.7172	Intermediate Similarity	NPC471738
0.717	Intermediate Similarity	NPC84042
0.717	Intermediate Similarity	NPC133907
0.717	Intermediate Similarity	NPC207885
0.717	Intermediate Similarity	NPC46998
0.717	Intermediate Similarity	NPC305085
0.717	Intermediate Similarity	NPC472753
0.717	Intermediate Similarity	NPC110443
0.717	Intermediate Similarity	NPC185141
0.717	Intermediate Similarity	NPC128733
0.717	Intermediate Similarity	NPC181645
0.7168	Intermediate Similarity	NPC473798
0.7167	Intermediate Similarity	NPC236999
0.7156	Intermediate Similarity	NPC144854
0.7156	Intermediate Similarity	NPC3316
0.7154	Intermediate Similarity	NPC475500
0.7154	Intermediate Similarity	NPC473548
0.7154	Intermediate Similarity	NPC182266
0.7154	Intermediate Similarity	NPC100017
0.7154	Intermediate Similarity	NPC475154
0.7154	Intermediate Similarity	NPC471136
0.7154	Intermediate Similarity	NPC471137
0.7154	Intermediate Similarity	NPC223356
0.7143	Intermediate Similarity	NPC298595
0.7143	Intermediate Similarity	NPC35717
0.7143	Intermediate Similarity	NPC473877
0.7143	Intermediate Similarity	NPC278008
0.7143	Intermediate Similarity	NPC474516
0.713	Intermediate Similarity	NPC477510
0.713	Intermediate Similarity	NPC297179
0.713	Intermediate Similarity	NPC478206
0.713	Intermediate Similarity	NPC108581
0.713	Intermediate Similarity	NPC471143
0.713	Intermediate Similarity	NPC478205
0.713	Intermediate Similarity	NPC204552
0.713	Intermediate Similarity	NPC106644
0.713	Intermediate Similarity	NPC188667
0.7119	Intermediate Similarity	NPC472399
0.7119	Intermediate Similarity	NPC280498
0.7119	Intermediate Similarity	NPC11895
0.7117	Intermediate Similarity	NPC100908
0.7115	Intermediate Similarity	NPC17585
0.7115	Intermediate Similarity	NPC8803
0.7115	Intermediate Similarity	NPC135576
0.7115	Intermediate Similarity	NPC93271
0.7115	Intermediate Similarity	NPC473859
0.7113	Intermediate Similarity	NPC477786
0.7113	Intermediate Similarity	NPC477784
0.7113	Intermediate Similarity	NPC477785
0.7107	Intermediate Similarity	NPC162495
0.7105	Intermediate Similarity	NPC476710
0.7105	Intermediate Similarity	NPC476711
0.7103	Intermediate Similarity	NPC472754
0.71	Intermediate Similarity	NPC281516
0.71	Intermediate Similarity	NPC472008
0.7091	Intermediate Similarity	NPC192813
0.7091	Intermediate Similarity	NPC277017
0.7091	Intermediate Similarity	NPC322903
0.7091	Intermediate Similarity	NPC293850
0.7091	Intermediate Similarity	NPC264819
0.7091	Intermediate Similarity	NPC154608
0.7087	Intermediate Similarity	NPC258674
0.7087	Intermediate Similarity	NPC474035
0.7087	Intermediate Similarity	NPC121825

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 NPC279722 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	194
0.1-0.2	1809
0.2-0.3	3943
0.3-0.4	2122
0.4-0.5	765
0.5-0.6	266
0.6-0.7	50
0.7-0.8	1
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
0.6923	Remote Similarity	NPD5282	Discontinued
0.6893	Remote Similarity	NPD7983	Approved
0.6864	Remote Similarity	NPD6319	Approved
0.6796	Remote Similarity	NPD6698	Approved
0.6796	Remote Similarity	NPD46	Approved
0.6768	Remote Similarity	NPD6110	Phase 1
0.6723	Remote Similarity	NPD6054	Approved
0.6697	Remote Similarity	NPD5344	Discontinued
0.6667	Remote Similarity	NPD4634	Approved
0.6667	Remote Similarity	NPD6016	Approved
0.6667	Remote Similarity	NPD5779	Approved
0.6667	Remote Similarity	NPD6015	Approved
0.6667	Remote Similarity	NPD5778	Approved
0.6637	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6635	Remote Similarity	NPD7838	Discovery
0.6634	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6612	Remote Similarity	NPD6370	Approved
0.6612	Remote Similarity	NPD5988	Approved
0.6606	Remote Similarity	NPD6648	Approved
0.6583	Remote Similarity	NPD6059	Approved
0.6557	Remote Similarity	NPD8328	Phase 3
0.6549	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6538	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6538	Remote Similarity	NPD6101	Approved
0.6522	Remote Similarity	NPD6371	Approved
0.6504	Remote Similarity	NPD7492	Approved
0.6496	Remote Similarity	NPD4632	Approved
0.6471	Remote Similarity	NPD7115	Discovery
0.6452	Remote Similarity	NPD6616	Approved
0.6415	Remote Similarity	NPD6411	Approved
0.641	Remote Similarity	NPD8297	Approved
0.6404	Remote Similarity	NPD5697	Approved
0.64	Remote Similarity	NPD7078	Approved
0.6364	Remote Similarity	NPD4225	Approved
0.6349	Remote Similarity	NPD7736	Approved
0.6348	Remote Similarity	NPD6899	Approved
0.6348	Remote Similarity	NPD6881	Approved
0.6333	Remote Similarity	NPD6009	Approved
0.6325	Remote Similarity	NPD6649	Approved
0.6325	Remote Similarity	NPD6650	Approved
0.6316	Remote Similarity	NPD6675	Approved
0.6316	Remote Similarity	NPD5739	Approved
0.6316	Remote Similarity	NPD6402	Approved
0.6316	Remote Similarity	NPD7128	Approved
0.6306	Remote Similarity	NPD5286	Approved
0.6306	Remote Similarity	NPD5285	Approved
0.6306	Remote Similarity	NPD4696	Approved
0.6304	Remote Similarity	NPD7331	Phase 2
0.6293	Remote Similarity	NPD6372	Approved
0.6293	Remote Similarity	NPD6014	Approved
0.6293	Remote Similarity	NPD6013	Approved
0.6293	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6293	Remote Similarity	NPD6373	Approved
0.6293	Remote Similarity	NPD6012	Approved
0.629	Remote Similarity	NPD7604	Phase 2
0.6273	Remote Similarity	NPD4755	Approved
0.627	Remote Similarity	NPD8293	Discontinued
0.6261	Remote Similarity	NPD5701	Approved
0.626	Remote Similarity	NPD5983	Phase 2
0.625	Remote Similarity	NPD5279	Phase 3
0.6239	Remote Similarity	NPD6883	Approved
0.6239	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6239	Remote Similarity	NPD7102	Approved
0.6239	Remote Similarity	NPD7290	Approved
0.6207	Remote Similarity	NPD7320	Approved
0.6207	Remote Similarity	NPD6011	Approved
0.6198	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6195	Remote Similarity	NPD5211	Phase 2
0.6195	Remote Similarity	NPD5226	Approved
0.6195	Remote Similarity	NPD5225	Approved
0.6195	Remote Similarity	NPD5224	Approved
0.6195	Remote Similarity	NPD4633	Approved
0.619	Remote Similarity	NPD7524	Approved
0.6186	Remote Similarity	NPD6617	Approved
0.6186	Remote Similarity	NPD6847	Approved
0.6186	Remote Similarity	NPD6869	Approved
0.6186	Remote Similarity	NPD8130	Phase 1
0.6182	Remote Similarity	NPD7839	Suspended
0.6182	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6182	Remote Similarity	NPD5222	Approved
0.6182	Remote Similarity	NPD4697	Phase 3
0.6182	Remote Similarity	NPD5221	Approved
0.6174	Remote Similarity	NPD6008	Approved
0.6162	Remote Similarity	NPD4756	Discovery
0.6161	Remote Similarity	NPD4700	Approved
0.6154	Remote Similarity	NPD1696	Phase 3
0.6148	Remote Similarity	NPD7641	Discontinued
0.614	Remote Similarity	NPD5175	Approved
0.614	Remote Similarity	NPD5174	Approved
0.6139	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6134	Remote Similarity	NPD6882	Approved
0.6129	Remote Similarity	NPD8516	Approved
0.6129	Remote Similarity	NPD8517	Approved
0.6129	Remote Similarity	NPD8515	Approved
0.6129	Remote Similarity	NPD3704	Approved
0.6129	Remote Similarity	NPD8513	Phase 3
0.6126	Remote Similarity	NPD5173	Approved
0.6111	Remote Similarity	NPD6079	Approved
0.6106	Remote Similarity	NPD5223	Approved
0.6102	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6095	Remote Similarity	NPD3618	Phase 1
0.6094	Remote Similarity	NPD6033	Approved
0.609	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6087	Remote Similarity	NPD5141	Approved
0.6075	Remote Similarity	NPD5328	Approved
0.6071	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6063	Remote Similarity	NPD6336	Discontinued
0.6032	Remote Similarity	NPD7829	Approved
0.6032	Remote Similarity	NPD7642	Approved
0.6032	Remote Similarity	NPD7830	Approved
0.6022	Remote Similarity	NPD7341	Phase 2
0.6019	Remote Similarity	NPD3168	Discontinued
0.6019	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.6	Remote Similarity	NPD6921	Approved
0.5984	Remote Similarity	NPD6274	Approved
0.5983	Remote Similarity	NPD6412	Phase 2
0.5982	Remote Similarity	NPD6084	Phase 2
0.5982	Remote Similarity	NPD6083	Phase 2
0.598	Remote Similarity	NPD4695	Discontinued
0.5978	Remote Similarity	NPD2664	Clinical (unspecified phase)
0.5957	Remote Similarity	NPD6108	Clinical (unspecified phase)
0.5952	Remote Similarity	NPD8080	Discontinued
0.5946	Remote Similarity	NPD5695	Phase 3
0.5946	Remote Similarity	NPD5210	Approved
0.5946	Remote Similarity	NPD4629	Approved
0.5943	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.5932	Remote Similarity	NPD4729	Approved
0.5932	Remote Similarity	NPD4730	Approved
0.5932	Remote Similarity	NPD6686	Approved
0.5932	Remote Similarity	NPD5128	Approved
0.5929	Remote Similarity	NPD5696	Approved
0.5926	Remote Similarity	NPD1695	Approved
0.5926	Remote Similarity	NPD4753	Phase 2
0.5923	Remote Similarity	NPD7319	Approved
0.5922	Remote Similarity	NPD5369	Approved
0.5917	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.5917	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.59	Remote Similarity	NPD818	Approved
0.59	Remote Similarity	NPD819	Approved
0.5897	Remote Similarity	NPD4768	Approved
0.5897	Remote Similarity	NPD4767	Approved
0.5891	Remote Similarity	NPD8074	Phase 3
0.5862	Remote Similarity	NPD4754	Approved
0.5849	Remote Similarity	NPD5363	Approved
0.5847	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.584	Remote Similarity	NPD7100	Approved
0.584	Remote Similarity	NPD7101	Approved
0.5833	Remote Similarity	NPD5249	Phase 3
0.5833	Remote Similarity	NPD5251	Approved
0.5833	Remote Similarity	NPD5248	Approved
0.5833	Remote Similarity	NPD5247	Approved
0.5833	Remote Similarity	NPD5250	Approved
0.5826	Remote Similarity	NPD1700	Approved
0.5818	Remote Similarity	NPD7637	Suspended
0.581	Remote Similarity	NPD6695	Phase 3
0.5806	Remote Similarity	NPD6317	Approved
0.5794	Remote Similarity	NPD4694	Approved
0.5794	Remote Similarity	NPD5786	Approved
0.5794	Remote Similarity	NPD5280	Approved
0.5785	Remote Similarity	NPD5217	Approved
0.5785	Remote Similarity	NPD5216	Approved
0.5785	Remote Similarity	NPD5215	Approved
0.5785	Remote Similarity	NPD7601	Clinical (unspecified phase)
0.5766	Remote Similarity	NPD4202	Approved
0.576	Remote Similarity	NPD6314	Approved
0.576	Remote Similarity	NPD6335	Approved
0.576	Remote Similarity	NPD6313	Approved
0.5758	Remote Similarity	NPD5956	Approved
0.5755	Remote Similarity	NPD3665	Phase 1
0.5755	Remote Similarity	NPD3666	Approved
0.5755	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.5755	Remote Similarity	NPD3133	Approved
0.575	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.5748	Remote Similarity	NPD8274	Clinical (unspecified phase)
0.5745	Remote Similarity	NPD3197	Phase 1
0.5741	Remote Similarity	NPD3573	Approved
0.5736	Remote Similarity	NPD8299	Approved
0.5736	Remote Similarity	NPD8340	Approved
0.5736	Remote Similarity	NPD8342	Approved
0.5736	Remote Similarity	NPD8341	Approved
0.5727	Remote Similarity	NPD5785	Approved
0.5726	Remote Similarity	NPD6868	Approved
0.5714	Remote Similarity	NPD7748	Approved
0.5714	Remote Similarity	NPD7260	Phase 2
0.5714	Remote Similarity	NPD4522	Approved
0.5714	Remote Similarity	NPD6435	Approved
0.5714	Remote Similarity	NPD3667	Approved
0.5702	Remote Similarity	NPD7902	Approved
0.5702	Remote Similarity	NPD5135	Approved
0.5702	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.5702	Remote Similarity	NPD5169	Approved
0.5701	Remote Similarity	NPD1694	Approved
0.5692	Remote Similarity	NPD7507	Approved
0.5692	Remote Similarity	NPD8273	Phase 1
0.5692	Remote Similarity	NPD8451	Approved
0.5676	Remote Similarity	NPD7515	Phase 2
0.5673	Remote Similarity	NPD6930	Phase 2
0.5673	Remote Similarity	NPD6931	Approved
0.5667	Remote Similarity	NPD5168	Approved
0.5664	Remote Similarity	NPD6190	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