NPASS Compound

Structure

NPC304180 OpenBabel07101718282D 28 30 0 0 1 0 0 0 0 0999 V2000 3.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0981 -0.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 1.5000 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 1.7321 2.0000 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 3.4641 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 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 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9511 -1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 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 5.1962 3.0000 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 1.7321 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.9511 0.3090 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 0.8660 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 6.0622 3.5000 0.0000 O 0 0 0 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 4.3301 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2601 1.2601 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.4067 0.9135 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5388 -0.5000 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 19 1 0 0 0 0 2 19 1 0 0 0 0 3 20 1 0 0 0 0 4 5 1 0 0 0 0 4 7 2 0 0 0 0 5 8 2 0 0 0 0 6 9 1 0 0 0 0 6 10 1 0 0 0 0 7 15 1 0 0 0 0 8 16 1 0 0 0 0 9 19 1 0 0 0 0 10 20 1 0 0 0 0 11 13 2 0 0 0 0 11 14 1 0 0 0 0 12 13 1 0 0 0 0 12 27 1 0 0 0 0 13 21 1 0 0 0 0 14 17 1 0 0 0 0 14 28 1 6 0 0 0 15 22 2 0 0 0 0 15 23 1 0 0 0 0 16 24 2 0 0 0 0 16 28 1 0 0 0 0 17 19 1 0 0 0 0 17 20 1 6 0 0 0 18 21 1 0 0 0 0 18 25 2 0 0 0 0 18 27 1 0 0 0 0 20 21 1 1 0 0 0 21 26 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	390.17
Volume:	391.816
LogP:	2.906
LogD:	2.346
LogS:	-3.952
# Rotatable Bonds:	5
TPSA:	110.13
# H-Bond Aceptor:	7
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.327
Synthetic Accessibility Score:	4.596
Fsp3:	0.571
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:	-5.207
MDCK Permeability:	1.2874750609626062e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.207
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.027
30% Bioavailability (F30%):	0.98

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.801
Plasma Protein Binding (PPB):	64.01948547363281%
Volume Distribution (VD):	0.252
Pgp-substrate:	28.36540985107422%

ADMET: Metabolism

CYP1A2-inhibitor:	0.086
CYP1A2-substrate:	0.167
CYP2C19-inhibitor:	0.107
CYP2C19-substrate:	0.068
CYP2C9-inhibitor:	0.493
CYP2C9-substrate:	0.894
CYP2D6-inhibitor:	0.172
CYP2D6-substrate:	0.247
CYP3A4-inhibitor:	0.258
CYP3A4-substrate:	0.22

ADMET: Excretion

Clearance (CL):	1.821
Half-life (T1/2):	0.063

ADMET: Toxicity

hERG Blockers:	0.001
Human Hepatotoxicity (H-HT):	0.29
Drug-inuced Liver Injury (DILI):	0.973
AMES Toxicity:	0.967
Rat Oral Acute Toxicity:	0.9
Maximum Recommended Daily Dose:	0.046
Skin Sensitization:	0.732
Carcinogencity:	0.948
Eye Corrosion:	0.892
Eye Irritation:	0.335
Respiratory Toxicity:	0.972

Download Data

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

Natural Product: NPC304180

Natural Product ID:	NPC304180
*Common Name:**	Mono 6-Strobilactone-B (E,E)-2,4-Hexadienedioic Acid Ester
IUPAC Name:	(2E,4E)-6-[[(5R,5aS,9aS,9bS)-9b-hydroxy-6,6,9a-trimethyl-1-oxo-3,5,5a,7,8,9-hexahydrobenzo[e][2]benzofuran-5-yl]oxy]-6-oxohexa-2,4-dienoic acid
Synonyms:
Standard InCHIKey:	WWELYLJKFRXUQW-BHEWPMNNSA-N
Standard InCHI:	InChI=1S/C21H26O7/c1-19(2)9-6-10-20(3)17(19)14(11-13-12-27-18(25)21(13,20)26)28-16(24)8-5-4-7-15(22)23/h4-5,7-8,11,14,17,26H,6,9-10,12H2,1-3H3,(H,22,23)/p-1/b7-4+,8-5+/t14-,17+,20+,21+/m1/s1
SMILES:	CC1(C)CCC[C@@]2(C)[C@H]1[C@@H](C=C1COC(=O)[C@]21O)OC(=O)/C=C/C=C/C(=O)[O-]
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1078134
PubChem CID:	44480216
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001634] Naphthofurans

*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
NPO27058	Aspergillus ustus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19769341]
NPO27058	Aspergillus ustus	Species	Aspergillaceae	Eukaryota	Suberites domuncula	n.a.	n.a.	PMID[19778087]
NPO27058	Aspergillus ustus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21348461]
NPO27058	Aspergillus ustus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24033077]
NPO27058	Aspergillus ustus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25706180]
NPO27058	Aspergillus ustus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[29286660]
NPO27058	Aspergillus ustus	Species	Aspergillaceae	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	3

Activity Type	# Activity
Cell Line	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1864	Cell Line	L5178Y	Mus musculus	EC50	=	5.3	ug.mL-1	PMID[548784]
NPT681	Cell Line	PC-12	Rattus norvegicus	EC50	>	10.0	ug.mL-1	PMID[548784]
NPT165	Cell Line	HeLa	Homo sapiens	EC50	>	10.0	ug.mL-1	PMID[548784]

☑ 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 NPC304180 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	194
0.1-0.2	972
0.2-0.3	3283
0.3-0.4	6410
0.4-0.5	12673
0.5-0.6	9122
0.6-0.7	6802
0.7-0.8	3071
0.8-0.85	145
0.85-0.9	14
0.9-0.95	3
0.95-1	8

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC179798
0.9808	High Similarity	NPC56448
0.9808	High Similarity	NPC469463
0.9808	High Similarity	NPC469454
0.9808	High Similarity	NPC469496
0.9709	High Similarity	NPC5103
0.9533	High Similarity	NPC23046
0.932	High Similarity	NPC477125
0.9223	High Similarity	NPC258532
0.9038	High Similarity	NPC146731
0.8857	High Similarity	NPC296950
0.8807	High Similarity	NPC269530
0.8624	High Similarity	NPC235014
0.8598	High Similarity	NPC469607
0.8584	High Similarity	NPC284707
0.8559	High Similarity	NPC471204
0.8558	High Similarity	NPC23364
0.8545	High Similarity	NPC188738
0.8496	Intermediate Similarity	NPC469684
0.8496	Intermediate Similarity	NPC53396
0.8496	Intermediate Similarity	NPC98249
0.8491	Intermediate Similarity	NPC295791
0.8491	Intermediate Similarity	NPC235369
0.8455	Intermediate Similarity	NPC210005
0.8455	Intermediate Similarity	NPC478211
0.8407	Intermediate Similarity	NPC270478
0.8407	Intermediate Similarity	NPC179626
0.8407	Intermediate Similarity	NPC176840
0.8407	Intermediate Similarity	NPC477509
0.8407	Intermediate Similarity	NPC478216
0.8393	Intermediate Similarity	NPC474271
0.8393	Intermediate Similarity	NPC25909
0.8378	Intermediate Similarity	NPC132790
0.8378	Intermediate Similarity	NPC247031
0.8378	Intermediate Similarity	NPC100329
0.8378	Intermediate Similarity	NPC97939
0.8376	Intermediate Similarity	NPC67251
0.8364	Intermediate Similarity	NPC141350
0.8364	Intermediate Similarity	NPC469370
0.835	Intermediate Similarity	NPC477129
0.835	Intermediate Similarity	NPC477130
0.8349	Intermediate Similarity	NPC187435
0.8349	Intermediate Similarity	NPC67321
0.8349	Intermediate Similarity	NPC3316
0.8349	Intermediate Similarity	NPC144854
0.8348	Intermediate Similarity	NPC270850
0.8348	Intermediate Similarity	NPC305260
0.8348	Intermediate Similarity	NPC475775
0.8348	Intermediate Similarity	NPC476529
0.8333	Intermediate Similarity	NPC473590
0.8333	Intermediate Similarity	NPC473968
0.8319	Intermediate Similarity	NPC474181
0.8318	Intermediate Similarity	NPC31058
0.8318	Intermediate Similarity	NPC469606
0.8318	Intermediate Similarity	NPC273005
0.8305	Intermediate Similarity	NPC470922
0.8305	Intermediate Similarity	NPC24651
0.8304	Intermediate Similarity	NPC126691
0.8304	Intermediate Similarity	NPC472002
0.8304	Intermediate Similarity	NPC476801
0.8304	Intermediate Similarity	NPC236217
0.8288	Intermediate Similarity	NPC286880
0.8288	Intermediate Similarity	NPC253906
0.8276	Intermediate Similarity	NPC109607
0.8276	Intermediate Similarity	NPC107338
0.8276	Intermediate Similarity	NPC474585
0.8276	Intermediate Similarity	NPC475885
0.8273	Intermediate Similarity	NPC275539
0.8273	Intermediate Similarity	NPC189075
0.8273	Intermediate Similarity	NPC154608
0.8273	Intermediate Similarity	NPC192813
0.8273	Intermediate Similarity	NPC476479
0.8273	Intermediate Similarity	NPC277017
0.8261	Intermediate Similarity	NPC153440
0.8257	Intermediate Similarity	NPC1679
0.8252	Intermediate Similarity	NPC475912
0.8246	Intermediate Similarity	NPC474734
0.8246	Intermediate Similarity	NPC190286
0.8241	Intermediate Similarity	NPC159533
0.8241	Intermediate Similarity	NPC23584
0.8241	Intermediate Similarity	NPC475945
0.8241	Intermediate Similarity	NPC475871
0.8235	Intermediate Similarity	NPC181999
0.823	Intermediate Similarity	NPC477126
0.823	Intermediate Similarity	NPC475966
0.823	Intermediate Similarity	NPC51978
0.823	Intermediate Similarity	NPC49451
0.8224	Intermediate Similarity	NPC474742
0.822	Intermediate Similarity	NPC469789
0.8214	Intermediate Similarity	NPC469656
0.8214	Intermediate Similarity	NPC317107
0.8214	Intermediate Similarity	NPC469655
0.8214	Intermediate Similarity	NPC474846
0.8208	Intermediate Similarity	NPC216478
0.8208	Intermediate Similarity	NPC222303
0.8205	Intermediate Similarity	NPC46570
0.8198	Intermediate Similarity	NPC478210
0.819	Intermediate Similarity	NPC236918
0.819	Intermediate Similarity	NPC156745
0.819	Intermediate Similarity	NPC268958
0.819	Intermediate Similarity	NPC5292
0.8182	Intermediate Similarity	NPC133422
0.8182	Intermediate Similarity	NPC110496
0.8182	Intermediate Similarity	NPC230541
0.8174	Intermediate Similarity	NPC176513
0.8174	Intermediate Similarity	NPC470775
0.8173	Intermediate Similarity	NPC469491
0.8167	Intermediate Similarity	NPC476008
0.8165	Intermediate Similarity	NPC474741
0.8165	Intermediate Similarity	NPC475676
0.8165	Intermediate Similarity	NPC220964
0.8158	Intermediate Similarity	NPC305044
0.8158	Intermediate Similarity	NPC265290
0.8155	Intermediate Similarity	NPC303697
0.8151	Intermediate Similarity	NPC8369
0.8151	Intermediate Similarity	NPC145238
0.8151	Intermediate Similarity	NPC476729
0.8148	Intermediate Similarity	NPC162973
0.8148	Intermediate Similarity	NPC149371
0.8148	Intermediate Similarity	NPC474747
0.8148	Intermediate Similarity	NPC11956
0.8148	Intermediate Similarity	NPC473596
0.8142	Intermediate Similarity	NPC317687
0.8142	Intermediate Similarity	NPC302146
0.8142	Intermediate Similarity	NPC474516
0.8136	Intermediate Similarity	NPC312833
0.8136	Intermediate Similarity	NPC107493
0.8131	Intermediate Similarity	NPC47024
0.8131	Intermediate Similarity	NPC471413
0.8131	Intermediate Similarity	NPC174314
0.8125	Intermediate Similarity	NPC37116
0.812	Intermediate Similarity	NPC19336
0.812	Intermediate Similarity	NPC185876
0.812	Intermediate Similarity	NPC48692
0.812	Intermediate Similarity	NPC472759
0.812	Intermediate Similarity	NPC329080
0.812	Intermediate Similarity	NPC79579
0.8113	Intermediate Similarity	NPC91695
0.8113	Intermediate Similarity	NPC208094
0.8113	Intermediate Similarity	NPC70145
0.8108	Intermediate Similarity	NPC476802
0.8108	Intermediate Similarity	NPC89171
0.8108	Intermediate Similarity	NPC264819
0.8108	Intermediate Similarity	NPC306265
0.8103	Intermediate Similarity	NPC472760
0.8103	Intermediate Similarity	NPC251310
0.8103	Intermediate Similarity	NPC478205
0.8103	Intermediate Similarity	NPC470776
0.8103	Intermediate Similarity	NPC21326
0.8103	Intermediate Similarity	NPC478206
0.8103	Intermediate Similarity	NPC108581
0.8099	Intermediate Similarity	NPC236999
0.8095	Intermediate Similarity	NPC295347
0.8095	Intermediate Similarity	NPC14961
0.8095	Intermediate Similarity	NPC270013
0.8095	Intermediate Similarity	NPC36954
0.8091	Intermediate Similarity	NPC102352
0.8091	Intermediate Similarity	NPC472749
0.8091	Intermediate Similarity	NPC472645
0.8091	Intermediate Similarity	NPC472751
0.8091	Intermediate Similarity	NPC478208
0.8087	Intermediate Similarity	NPC470628
0.8087	Intermediate Similarity	NPC96312
0.8087	Intermediate Similarity	NPC40632
0.8087	Intermediate Similarity	NPC474046
0.8087	Intermediate Similarity	NPC207217
0.8087	Intermediate Similarity	NPC251236
0.8087	Intermediate Similarity	NPC148458
0.8087	Intermediate Similarity	NPC259306
0.8087	Intermediate Similarity	NPC328374
0.8083	Intermediate Similarity	NPC293112
0.8083	Intermediate Similarity	NPC477745
0.8077	Intermediate Similarity	NPC476300
0.8077	Intermediate Similarity	NPC475657
0.8073	Intermediate Similarity	NPC472755
0.8073	Intermediate Similarity	NPC472747
0.8073	Intermediate Similarity	NPC473624
0.8073	Intermediate Similarity	NPC472750
0.8073	Intermediate Similarity	NPC99266
0.8073	Intermediate Similarity	NPC474775
0.8073	Intermediate Similarity	NPC475321
0.8073	Intermediate Similarity	NPC4620
0.8073	Intermediate Similarity	NPC254202
0.807	Intermediate Similarity	NPC101965
0.807	Intermediate Similarity	NPC478212
0.807	Intermediate Similarity	NPC101400
0.8067	Intermediate Similarity	NPC105926
0.8067	Intermediate Similarity	NPC265557
0.8067	Intermediate Similarity	NPC18945
0.8067	Intermediate Similarity	NPC120724
0.8067	Intermediate Similarity	NPC91693
0.8058	Intermediate Similarity	NPC51004
0.8056	Intermediate Similarity	NPC472753
0.8056	Intermediate Similarity	NPC308824
0.8056	Intermediate Similarity	NPC471412
0.8056	Intermediate Similarity	NPC47880
0.8056	Intermediate Similarity	NPC469657
0.8056	Intermediate Similarity	NPC244456
0.8053	Intermediate Similarity	NPC475668
0.8053	Intermediate Similarity	NPC473921

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 NPC304180 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	164
0.1-0.2	1181
0.2-0.3	3308
0.3-0.4	2720
0.4-0.5	1103
0.5-0.6	373
0.6-0.7	228
0.7-0.8	73
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
0.787	Intermediate Similarity	NPD4225	Approved
0.7759	Intermediate Similarity	NPD4632	Approved
0.7712	Intermediate Similarity	NPD7115	Discovery
0.7667	Intermediate Similarity	NPD6319	Approved
0.7632	Intermediate Similarity	NPD6686	Approved
0.7619	Intermediate Similarity	NPD7260	Phase 2
0.7565	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7544	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7544	Intermediate Similarity	NPD5697	Approved
0.7521	Intermediate Similarity	NPD8297	Approved
0.75	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7478	Intermediate Similarity	NPD6881	Approved
0.7478	Intermediate Similarity	NPD6899	Approved
0.7478	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7459	Intermediate Similarity	NPD8513	Phase 3
0.7459	Intermediate Similarity	NPD8516	Approved
0.7459	Intermediate Similarity	NPD8517	Approved
0.7459	Intermediate Similarity	NPD8515	Approved
0.7436	Intermediate Similarity	NPD6649	Approved
0.7436	Intermediate Similarity	NPD6650	Approved
0.7419	Intermediate Similarity	NPD7492	Approved
0.7417	Intermediate Similarity	NPD6009	Approved
0.7414	Intermediate Similarity	NPD6013	Approved
0.7414	Intermediate Similarity	NPD6014	Approved
0.7414	Intermediate Similarity	NPD6012	Approved
0.7407	Intermediate Similarity	NPD5779	Approved
0.7407	Intermediate Similarity	NPD5778	Approved
0.7404	Intermediate Similarity	NPD1694	Approved
0.7377	Intermediate Similarity	NPD6054	Approved
0.736	Intermediate Similarity	NPD6616	Approved
0.735	Intermediate Similarity	NPD7290	Approved
0.735	Intermediate Similarity	NPD6883	Approved
0.735	Intermediate Similarity	NPD7102	Approved
0.735	Intermediate Similarity	NPD6371	Approved
0.7345	Intermediate Similarity	NPD5211	Phase 2
0.7328	Intermediate Similarity	NPD6011	Approved
0.7321	Intermediate Similarity	NPD7639	Approved
0.7321	Intermediate Similarity	NPD6648	Approved
0.7321	Intermediate Similarity	NPD7640	Approved
0.7317	Intermediate Similarity	NPD5983	Phase 2
0.7317	Intermediate Similarity	NPD6016	Approved
0.7317	Intermediate Similarity	NPD6015	Approved
0.7315	Intermediate Similarity	NPD7983	Approved
0.7304	Intermediate Similarity	NPD7128	Approved
0.7304	Intermediate Similarity	NPD5739	Approved
0.7304	Intermediate Similarity	NPD6675	Approved
0.7304	Intermediate Similarity	NPD6008	Approved
0.7304	Intermediate Similarity	NPD6402	Approved
0.7302	Intermediate Similarity	NPD7078	Approved
0.7288	Intermediate Similarity	NPD6869	Approved
0.7288	Intermediate Similarity	NPD6617	Approved
0.7288	Intermediate Similarity	NPD8413	Clinical (unspecified phase)
0.7288	Intermediate Similarity	NPD8130	Phase 1
0.7288	Intermediate Similarity	NPD6847	Approved
0.7287	Intermediate Similarity	NPD6845	Suspended
0.7273	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7265	Intermediate Similarity	NPD6372	Approved
0.7265	Intermediate Similarity	NPD6373	Approved
0.7258	Intermediate Similarity	NPD6370	Approved
0.7258	Intermediate Similarity	NPD5988	Approved
0.7257	Intermediate Similarity	NPD5344	Discontinued
0.7244	Intermediate Similarity	NPD7736	Approved
0.7241	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD5701	Approved
0.7232	Intermediate Similarity	NPD8029	Clinical (unspecified phase)
0.7232	Intermediate Similarity	NPD7638	Approved
0.7227	Intermediate Similarity	NPD6053	Discontinued
0.7227	Intermediate Similarity	NPD6882	Approved
0.7222	Intermediate Similarity	NPD7838	Discovery
0.7222	Intermediate Similarity	NPD7507	Approved
0.7222	Intermediate Similarity	NPD6698	Approved
0.7222	Intermediate Similarity	NPD46	Approved
0.7217	Intermediate Similarity	NPD5141	Approved
0.7203	Intermediate Similarity	NPD4634	Approved
0.72	Intermediate Similarity	NPD7604	Phase 2
0.7182	Intermediate Similarity	NPD5282	Discontinued
0.7179	Intermediate Similarity	NPD7320	Approved
0.7177	Intermediate Similarity	NPD7503	Approved
0.7168	Intermediate Similarity	NPD5286	Approved
0.7168	Intermediate Similarity	NPD4696	Approved
0.7168	Intermediate Similarity	NPD5285	Approved
0.7165	Intermediate Similarity	NPD8074	Phase 3
0.7117	Intermediate Similarity	NPD5695	Phase 3
0.7115	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD6059	Approved
0.7087	Intermediate Similarity	NPD6336	Discontinued
0.708	Intermediate Similarity	NPD5696	Approved
0.7075	Intermediate Similarity	NPD1733	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD8328	Phase 3
0.7054	Intermediate Similarity	NPD7319	Approved
0.7043	Intermediate Similarity	NPD4633	Approved
0.7043	Intermediate Similarity	NPD5226	Approved
0.7043	Intermediate Similarity	NPD5224	Approved
0.7043	Intermediate Similarity	NPD5225	Approved
0.7031	Intermediate Similarity	NPD8293	Discontinued
0.7	Intermediate Similarity	NPD5281	Approved
0.7	Intermediate Similarity	NPD6411	Approved
0.7	Intermediate Similarity	NPD5284	Approved
0.6991	Remote Similarity	NPD6083	Phase 2
0.6991	Remote Similarity	NPD4755	Approved
0.6991	Remote Similarity	NPD6084	Phase 2
0.6983	Remote Similarity	NPD5175	Approved
0.6983	Remote Similarity	NPD5174	Approved
0.6957	Remote Similarity	NPD5223	Approved
0.6949	Remote Similarity	NPD6412	Phase 2
0.694	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6937	Remote Similarity	NPD6399	Phase 3
0.6911	Remote Similarity	NPD6274	Approved
0.6905	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6903	Remote Similarity	NPD5221	Approved
0.6903	Remote Similarity	NPD5222	Approved
0.6903	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.688	Remote Similarity	NPD7101	Approved
0.688	Remote Similarity	NPD7100	Approved
0.687	Remote Similarity	NPD4700	Approved
0.686	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6855	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6855	Remote Similarity	NPD6317	Approved
0.6847	Remote Similarity	NPD5693	Phase 1
0.6847	Remote Similarity	NPD5694	Approved
0.6847	Remote Similarity	NPD7637	Suspended
0.6842	Remote Similarity	NPD5173	Approved
0.6842	Remote Similarity	NPD7902	Approved
0.6818	Remote Similarity	NPD6101	Approved
0.6818	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6814	Remote Similarity	NPD5210	Approved
0.6814	Remote Similarity	NPD4629	Approved
0.68	Remote Similarity	NPD6313	Approved
0.68	Remote Similarity	NPD6335	Approved
0.68	Remote Similarity	NPD6314	Approved
0.6789	Remote Similarity	NPD3573	Approved
0.6772	Remote Similarity	NPD6921	Approved
0.6757	Remote Similarity	NPD5207	Approved
0.6757	Remote Similarity	NPD5785	Approved
0.6757	Remote Similarity	NPD5692	Phase 3
0.6754	Remote Similarity	NPD4697	Phase 3
0.6752	Remote Similarity	NPD7632	Discontinued
0.675	Remote Similarity	NPD4730	Approved
0.675	Remote Similarity	NPD4729	Approved
0.6727	Remote Similarity	NPD6672	Approved
0.6727	Remote Similarity	NPD5737	Approved
0.6726	Remote Similarity	NPD7748	Approved
0.6697	Remote Similarity	NPD5279	Phase 3
0.6696	Remote Similarity	NPD6050	Approved
0.6696	Remote Similarity	NPD6079	Approved
0.6667	Remote Similarity	NPD4753	Phase 2
0.6667	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7327	Approved
0.6667	Remote Similarity	NPD1695	Approved
0.6667	Remote Similarity	NPD7328	Approved
0.6641	Remote Similarity	NPD8033	Approved
0.664	Remote Similarity	NPD6868	Approved
0.6639	Remote Similarity	NPD5250	Approved
0.6639	Remote Similarity	NPD5249	Phase 3
0.6639	Remote Similarity	NPD5248	Approved
0.6639	Remote Similarity	NPD5247	Approved
0.6639	Remote Similarity	NPD5251	Approved
0.6636	Remote Similarity	NPD7524	Approved
0.6614	Remote Similarity	NPD7516	Approved
0.6612	Remote Similarity	NPD5128	Approved
0.6606	Remote Similarity	NPD1696	Phase 3
0.6604	Remote Similarity	NPD4695	Discontinued
0.6591	Remote Similarity	NPD6033	Approved
0.6585	Remote Similarity	NPD5217	Approved
0.6585	Remote Similarity	NPD5216	Approved
0.6585	Remote Similarity	NPD5215	Approved
0.6583	Remote Similarity	NPD4767	Approved
0.6583	Remote Similarity	NPD4768	Approved
0.6579	Remote Similarity	NPD7900	Approved
0.6579	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6562	Remote Similarity	NPD8377	Approved
0.6562	Remote Similarity	NPD8294	Approved
0.6557	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6555	Remote Similarity	NPD4754	Approved
0.6549	Remote Similarity	NPD7515	Phase 2
0.6545	Remote Similarity	NPD4519	Discontinued
0.6545	Remote Similarity	NPD5280	Approved
0.6545	Remote Similarity	NPD3618	Phase 1
0.6545	Remote Similarity	NPD7334	Approved
0.6545	Remote Similarity	NPD4623	Approved
0.6545	Remote Similarity	NPD4694	Approved
0.6545	Remote Similarity	NPD5690	Phase 2
0.6545	Remote Similarity	NPD6409	Approved
0.6545	Remote Similarity	NPD7521	Approved
0.6545	Remote Similarity	NPD6684	Approved
0.6545	Remote Similarity	NPD5330	Approved
0.6545	Remote Similarity	NPD7146	Approved
0.6522	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6518	Remote Similarity	NPD6080	Approved
0.6518	Remote Similarity	NPD6673	Approved
0.6518	Remote Similarity	NPD6904	Approved
0.6518	Remote Similarity	NPD5328	Approved
0.6514	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6512	Remote Similarity	NPD6908	Approved
0.6512	Remote Similarity	NPD8380	Approved
0.6512	Remote Similarity	NPD8335	Approved
0.6512	Remote Similarity	NPD8379	Approved
0.6512	Remote Similarity	NPD6909	Approved
0.6512	Remote Similarity	NPD8378	Approved
0.6512	Remote Similarity	NPD8296	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