NPASS Compound

Structure

NPC80800 OpenBabel07101718312D 30 30 0 0 1 0 0 0 0 0999 V2000 -2.5981 11.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 13.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 8.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 5.5000 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 -0.5000 2.1340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 10.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 7.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 11.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 10.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 8.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 7.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 5.5000 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 0.0000 4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 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 -1.7321 12.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 9.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 C 0 0 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 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 3.0000 0.0000 C 0 0 2 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 0.8660 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0000 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 20 1 0 0 0 0 2 20 1 0 0 0 0 3 21 1 0 0 0 0 4 22 1 0 0 0 0 5 23 1 0 0 0 0 7 10 1 0 0 0 0 7 11 1 0 0 0 0 8 12 1 0 0 0 0 8 13 1 0 0 0 0 9 14 1 0 0 0 0 9 16 1 0 0 0 0 10 20 2 0 0 0 0 11 21 1 0 0 0 0 12 21 2 0 0 0 0 13 22 1 0 0 0 0 14 22 2 0 0 0 0 15 17 2 0 0 0 0 15 24 1 0 0 0 0 16 27 1 0 0 0 0 17 27 1 0 0 0 0 18 23 2 0 0 0 0 18 26 1 0 0 0 0 19 24 1 0 0 0 0 19 25 2 0 0 0 0 23 25 1 0 0 0 0 24 26 2 0 0 0 0 25 28 1 0 0 0 0 26 29 1 0 0 0 0 27 6 1 6 0 0 0 27 30 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	412.3
Volume:	474.907
LogP:	6.89
LogD:	4.99
LogS:	-3.883
# Rotatable Bonds:	11
TPSA:	60.69
# H-Bond Aceptor:	3
# H-Bond Donor:	3
# Rings:	1
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.263
Synthetic Accessibility Score:	3.706
Fsp3:	0.481
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.805
MDCK Permeability:	2.689250322873704e-05
Pgp-inhibitor:	0.411
Pgp-substrate:	0.301
Human Intestinal Absorption (HIA):	0.014
20% Bioavailability (F20%):	0.945
30% Bioavailability (F30%):	0.859

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.031
Plasma Protein Binding (PPB):	99.42142486572266%
Volume Distribution (VD):	0.678
Pgp-substrate:	0.7209377288818359%

ADMET: Metabolism

CYP1A2-inhibitor:	0.752
CYP1A2-substrate:	0.169
CYP2C19-inhibitor:	0.734
CYP2C19-substrate:	0.49
CYP2C9-inhibitor:	0.674
CYP2C9-substrate:	0.952
CYP2D6-inhibitor:	0.946
CYP2D6-substrate:	0.071
CYP3A4-inhibitor:	0.885
CYP3A4-substrate:	0.191

ADMET: Excretion

Clearance (CL):	10.019
Half-life (T1/2):	0.307

ADMET: Toxicity

hERG Blockers:	0.087
Human Hepatotoxicity (H-HT):	0.848
Drug-inuced Liver Injury (DILI):	0.01
AMES Toxicity:	0.003
Rat Oral Acute Toxicity:	0.005
Maximum Recommended Daily Dose:	0.938
Skin Sensitization:	0.94
Carcinogencity:	0.039
Eye Corrosion:	0.015
Eye Irritation:	0.893
Respiratory Toxicity:	0.125

Download Data

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

Natural Product: NPC80800

Natural Product ID:	NPC80800
*Common Name:**	Chabrolohydroxybenzoquinone E
IUPAC Name:	2-[(1Z,3S,6E,10E)-3-hydroxy-3,7,11,15-tetramethylhexadeca-1,6,10,14-tetraenyl]-5-methylbenzene-1,4-diol
Synonyms:	Chabrolohydroxybenzoquinone E
Standard InCHIKey:	XWQHOLPJPWBQKN-JUIZPVCTSA-N
Standard InCHI:	InChI=1S/C27H40O3/c1-20(2)10-7-11-21(3)12-8-13-22(4)14-9-16-27(6,30)17-15-24-19-25(28)23(5)18-26(24)29/h10,12,14-15,17-19,28-30H,7-9,11,13,16H2,1-6H3/b17-15-,21-12+,22-14+/t27-/m0/s1
SMILES:	CC(=CCC/C(=C/CC/C(=C/CC[C@@](C)(/C=Cc1cc(c(C)cc1O)O)O)/C)/C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL463707
PubChem CID:	44566531
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids

*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
NPO16934	Nephthea chabrolii	Species	Nephtheidae	Eukaryota	n.a.	Formosan soft coral	n.a.	PMID[16309317]
NPO16934	Nephthea chabrolii	Species	Nephtheidae	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
IC50	3

Activity Type	# Activity
Cell Line	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT65	Cell Line	HepG2	Homo sapiens	IC50	>	48500.0	nM	PMID[492289]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	48500.0	nM	PMID[492289]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	IC50	>	48500.0	nM	PMID[492289]

☑ 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 NPC80800 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	253
0.1-0.2	1811
0.2-0.3	5542
0.3-0.4	13990
0.4-0.5	6163
0.5-0.6	10343
0.6-0.7	3558
0.7-0.8	793
0.8-0.85	162
0.85-0.9	59
0.9-0.95	17
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
0.9681	High Similarity	NPC475078
0.9583	High Similarity	NPC477685
0.9579	High Similarity	NPC260775
0.9495	High Similarity	NPC474352
0.9479	High Similarity	NPC129373
0.9479	High Similarity	NPC130756
0.9479	High Similarity	NPC12931
0.9479	High Similarity	NPC70677
0.9479	High Similarity	NPC248396
0.9479	High Similarity	NPC48730
0.9474	High Similarity	NPC152097
0.9394	High Similarity	NPC53740
0.9293	High Similarity	NPC47284
0.9286	High Similarity	NPC108497
0.9255	High Similarity	NPC29373
0.9149	High Similarity	NPC231150
0.9082	High Similarity	NPC72729
0.901	High Similarity	NPC155072
0.901	High Similarity	NPC469913
0.899	High Similarity	NPC252105
0.8942	High Similarity	NPC469912
0.89	High Similarity	NPC235762
0.89	High Similarity	NPC471228
0.8889	High Similarity	NPC174911
0.8878	High Similarity	NPC79241
0.8878	High Similarity	NPC6597
0.8854	High Similarity	NPC94139
0.8854	High Similarity	NPC210497
0.8854	High Similarity	NPC147284
0.8854	High Similarity	NPC3358
0.8854	High Similarity	NPC162314
0.8854	High Similarity	NPC306884
0.8812	High Similarity	NPC272029
0.8812	High Similarity	NPC475225
0.8788	High Similarity	NPC299762
0.8788	High Similarity	NPC33675
0.8776	High Similarity	NPC312132
0.8776	High Similarity	NPC259512
0.8762	High Similarity	NPC54373
0.8738	High Similarity	NPC66834
0.8738	High Similarity	NPC232523
0.8738	High Similarity	NPC158253
0.8738	High Similarity	NPC204901
0.8738	High Similarity	NPC320439
0.8713	High Similarity	NPC269212
0.87	High Similarity	NPC130103
0.8687	High Similarity	NPC88420
0.8679	High Similarity	NPC62867
0.8679	High Similarity	NPC177962
0.8679	High Similarity	NPC302371
0.8667	High Similarity	NPC471535
0.8646	High Similarity	NPC192
0.8641	High Similarity	NPC12640
0.8641	High Similarity	NPC99836
0.8641	High Similarity	NPC310456
0.8641	High Similarity	NPC201662
0.8632	High Similarity	NPC27974
0.8627	High Similarity	NPC475580
0.8627	High Similarity	NPC130817
0.8614	High Similarity	NPC12221
0.8585	High Similarity	NPC77772
0.8585	High Similarity	NPC266937
0.8585	High Similarity	NPC470770
0.8571	High Similarity	NPC245187
0.8571	High Similarity	NPC282855
0.8571	High Similarity	NPC26013
0.8571	High Similarity	NPC98392
0.8571	High Similarity	NPC473524
0.8558	High Similarity	NPC233320
0.8545	High Similarity	NPC206205
0.8544	High Similarity	NPC37802
0.8532	High Similarity	NPC141001
0.8529	High Similarity	NPC233827
0.8526	High Similarity	NPC307235
0.8526	High Similarity	NPC407
0.8511	High Similarity	NPC286904
0.8511	High Similarity	NPC150837
0.8505	High Similarity	NPC228452
0.8505	High Similarity	NPC474920
0.85	High Similarity	NPC474073
0.8491	Intermediate Similarity	NPC208229
0.8485	Intermediate Similarity	NPC32714
0.8476	Intermediate Similarity	NPC279887
0.8476	Intermediate Similarity	NPC68260
0.8476	Intermediate Similarity	NPC306295
0.8455	Intermediate Similarity	NPC320864
0.8454	Intermediate Similarity	NPC55561
0.8454	Intermediate Similarity	NPC312304
0.8447	Intermediate Similarity	NPC93831
0.8447	Intermediate Similarity	NPC227458
0.8447	Intermediate Similarity	NPC218879
0.8447	Intermediate Similarity	NPC244513
0.8421	Intermediate Similarity	NPC155393
0.8411	Intermediate Similarity	NPC228609
0.8396	Intermediate Similarity	NPC33728
0.8396	Intermediate Similarity	NPC19808
0.8384	Intermediate Similarity	NPC152415
0.8384	Intermediate Similarity	NPC76938
0.8367	Intermediate Similarity	NPC270547
0.8365	Intermediate Similarity	NPC117115
0.8351	Intermediate Similarity	NPC280347
0.8351	Intermediate Similarity	NPC177420
0.835	Intermediate Similarity	NPC196479
0.835	Intermediate Similarity	NPC222522
0.835	Intermediate Similarity	NPC106396
0.835	Intermediate Similarity	NPC168303
0.835	Intermediate Similarity	NPC146798
0.835	Intermediate Similarity	NPC249828
0.835	Intermediate Similarity	NPC302219
0.835	Intermediate Similarity	NPC85479
0.835	Intermediate Similarity	NPC53051
0.835	Intermediate Similarity	NPC313030
0.835	Intermediate Similarity	NPC242342
0.835	Intermediate Similarity	NPC24404
0.835	Intermediate Similarity	NPC94351
0.835	Intermediate Similarity	NPC71002
0.8349	Intermediate Similarity	NPC471534
0.8333	Intermediate Similarity	NPC166761
0.8333	Intermediate Similarity	NPC166995
0.8318	Intermediate Similarity	NPC132720
0.8304	Intermediate Similarity	NPC471449
0.8302	Intermediate Similarity	NPC174981
0.8286	Intermediate Similarity	NPC67250
0.8286	Intermediate Similarity	NPC54765
0.8283	Intermediate Similarity	NPC55903
0.8273	Intermediate Similarity	NPC232165
0.8273	Intermediate Similarity	NPC473718
0.8257	Intermediate Similarity	NPC28784
0.8257	Intermediate Similarity	NPC296144
0.8252	Intermediate Similarity	NPC72947
0.8252	Intermediate Similarity	NPC24407
0.8252	Intermediate Similarity	NPC284011
0.8252	Intermediate Similarity	NPC166313
0.8252	Intermediate Similarity	NPC147310
0.8252	Intermediate Similarity	NPC294186
0.8252	Intermediate Similarity	NPC11280
0.8252	Intermediate Similarity	NPC137415
0.8252	Intermediate Similarity	NPC192032
0.8247	Intermediate Similarity	NPC19680
0.8247	Intermediate Similarity	NPC113460
0.8247	Intermediate Similarity	NPC25493
0.8241	Intermediate Similarity	NPC275627
0.8241	Intermediate Similarity	NPC224527
0.8224	Intermediate Similarity	NPC299568
0.8224	Intermediate Similarity	NPC186385
0.8208	Intermediate Similarity	NPC151477
0.8198	Intermediate Similarity	NPC69539
0.819	Intermediate Similarity	NPC138942
0.8182	Intermediate Similarity	NPC204210
0.8182	Intermediate Similarity	NPC474050
0.8182	Intermediate Similarity	NPC306074
0.8182	Intermediate Similarity	NPC473931
0.8182	Intermediate Similarity	NPC474114
0.8182	Intermediate Similarity	NPC114918
0.8182	Intermediate Similarity	NPC197513
0.8165	Intermediate Similarity	NPC46940
0.8165	Intermediate Similarity	NPC26615
0.8163	Intermediate Similarity	NPC98772
0.8163	Intermediate Similarity	NPC318325
0.8163	Intermediate Similarity	NPC242240
0.8163	Intermediate Similarity	NPC123273
0.8158	Intermediate Similarity	NPC45663
0.8155	Intermediate Similarity	NPC225506
0.8155	Intermediate Similarity	NPC10588
0.8155	Intermediate Similarity	NPC294741
0.8148	Intermediate Similarity	NPC296683
0.8144	Intermediate Similarity	NPC184169
0.8144	Intermediate Similarity	NPC23167
0.8142	Intermediate Similarity	NPC151197
0.8142	Intermediate Similarity	NPC121866
0.8142	Intermediate Similarity	NPC51341
0.8137	Intermediate Similarity	NPC156313
0.8137	Intermediate Similarity	NPC77492
0.8131	Intermediate Similarity	NPC169450
0.8131	Intermediate Similarity	NPC64586
0.8131	Intermediate Similarity	NPC95344
0.8131	Intermediate Similarity	NPC241549
0.8125	Intermediate Similarity	NPC187993
0.8125	Intermediate Similarity	NPC238176
0.8125	Intermediate Similarity	NPC248817
0.8119	Intermediate Similarity	NPC274678
0.8119	Intermediate Similarity	NPC26244
0.8119	Intermediate Similarity	NPC222146
0.8113	Intermediate Similarity	NPC21594
0.8095	Intermediate Similarity	NPC238696
0.8095	Intermediate Similarity	NPC323810
0.8095	Intermediate Similarity	NPC288411
0.8091	Intermediate Similarity	NPC261343
0.8091	Intermediate Similarity	NPC263753
0.8091	Intermediate Similarity	NPC76400
0.8091	Intermediate Similarity	NPC117846
0.8091	Intermediate Similarity	NPC23804
0.8091	Intermediate Similarity	NPC190212
0.8087	Intermediate Similarity	NPC168707
0.8087	Intermediate Similarity	NPC48623
0.8081	Intermediate Similarity	NPC47950
0.8073	Intermediate Similarity	NPC95716
0.807	Intermediate Similarity	NPC325544
0.807	Intermediate Similarity	NPC477037
0.807	Intermediate Similarity	NPC318581

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 NPC80800 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	249
0.1-0.2	1086
0.2-0.3	1532
0.3-0.4	3044
0.4-0.5	1796
0.5-0.6	1079
0.6-0.7	308
0.7-0.8	45
0.8-0.85	7
0.85-0.9	3
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9062	High Similarity	NPD844	Approved
0.8889	High Similarity	NPD289	Clinical (unspecified phase)
0.8776	High Similarity	NPD288	Approved
0.8679	High Similarity	NPD7635	Approved
0.844	Intermediate Similarity	NPD6671	Approved
0.8224	Intermediate Similarity	NPD4750	Phase 3
0.82	Intermediate Similarity	NPD2934	Approved
0.82	Intermediate Similarity	NPD2933	Approved
0.8119	Intermediate Similarity	NPD2859	Approved
0.8119	Intermediate Similarity	NPD2860	Approved
0.81	Intermediate Similarity	NPD845	Approved
0.8058	Intermediate Similarity	NPD3020	Approved
0.8021	Intermediate Similarity	NPD111	Approved
0.802	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.7905	Intermediate Similarity	NPD846	Approved
0.7905	Intermediate Similarity	NPD940	Approved
0.787	Intermediate Similarity	NPD2342	Discontinued
0.7767	Intermediate Similarity	NPD1809	Phase 2
0.7731	Intermediate Similarity	NPD6696	Suspended
0.7727	Intermediate Similarity	NPD3022	Approved
0.7727	Intermediate Similarity	NPD3021	Approved
0.766	Intermediate Similarity	NPD9088	Approved
0.7642	Intermediate Similarity	NPD1242	Phase 1
0.7615	Intermediate Similarity	NPD1444	Approved
0.7615	Intermediate Similarity	NPD1445	Approved
0.7565	Intermediate Similarity	NPD7340	Approved
0.7544	Intermediate Similarity	NPD497	Approved
0.7456	Intermediate Similarity	NPD495	Approved
0.7456	Intermediate Similarity	NPD1398	Phase 1
0.7456	Intermediate Similarity	NPD498	Approved
0.7456	Intermediate Similarity	NPD496	Approved
0.7455	Intermediate Similarity	NPD968	Approved
0.7453	Intermediate Similarity	NPD9273	Approved
0.7411	Intermediate Similarity	NPD1792	Phase 2
0.7395	Intermediate Similarity	NPD3496	Discontinued
0.7355	Intermediate Similarity	NPD4749	Approved
0.7339	Intermediate Similarity	NPD9500	Approved
0.7311	Intermediate Similarity	NPD4626	Approved
0.7311	Intermediate Similarity	NPD4059	Approved
0.7304	Intermediate Similarity	NPD2229	Approved
0.7304	Intermediate Similarity	NPD2228	Approved
0.7304	Intermediate Similarity	NPD2234	Approved
0.7288	Intermediate Similarity	NPD3091	Approved
0.7288	Intermediate Similarity	NPD2226	Clinical (unspecified phase)
0.7281	Intermediate Similarity	NPD6124	Clinical (unspecified phase)
0.7281	Intermediate Similarity	NPD228	Approved
0.7265	Intermediate Similarity	NPD7325	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD1981	Approved
0.725	Intermediate Similarity	NPD1983	Approved
0.725	Intermediate Similarity	NPD1980	Approved
0.7241	Intermediate Similarity	NPD9618	Approved
0.7241	Intermediate Similarity	NPD9614	Approved
0.7234	Intermediate Similarity	NPD9087	Approved
0.7184	Intermediate Similarity	NPD9295	Approved
0.7167	Intermediate Similarity	NPD1778	Approved
0.7167	Intermediate Similarity	NPD3019	Approved
0.7167	Intermediate Similarity	NPD2932	Approved
0.7156	Intermediate Similarity	NPD3028	Approved
0.7155	Intermediate Similarity	NPD7159	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD4625	Phase 3
0.7131	Intermediate Similarity	NPD2230	Approved
0.7131	Intermediate Similarity	NPD2232	Approved
0.7131	Intermediate Similarity	NPD2233	Approved
0.712	Intermediate Similarity	NPD2861	Phase 2
0.7117	Intermediate Similarity	NPD9610	Approved
0.7117	Intermediate Similarity	NPD9608	Approved
0.7094	Intermediate Similarity	NPD1791	Approved
0.7094	Intermediate Similarity	NPD1793	Approved
0.7087	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.708	Intermediate Similarity	NPD290	Approved
0.7073	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7069	Intermediate Similarity	NPD9379	Approved
0.7069	Intermediate Similarity	NPD9377	Approved
0.7059	Intermediate Similarity	NPD9613	Approved
0.7059	Intermediate Similarity	NPD9616	Approved
0.7059	Intermediate Similarity	NPD9615	Approved
0.7049	Intermediate Similarity	NPD5351	Clinical (unspecified phase)
0.7049	Intermediate Similarity	NPD3092	Approved
0.7049	Intermediate Similarity	NPD5350	Clinical (unspecified phase)
0.7043	Intermediate Similarity	NPD9280	Clinical (unspecified phase)
0.704	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD2286	Discontinued
0.701	Intermediate Similarity	NPD9294	Approved
0.7	Intermediate Similarity	NPD316	Approved
0.6975	Remote Similarity	NPD405	Clinical (unspecified phase)
0.696	Remote Similarity	NPD3094	Phase 2
0.6942	Remote Similarity	NPD4093	Discontinued
0.6942	Remote Similarity	NPD5691	Approved
0.6929	Remote Similarity	NPD600	Approved
0.6929	Remote Similarity	NPD596	Approved
0.6911	Remote Similarity	NPD1201	Approved
0.6911	Remote Similarity	NPD1611	Approved
0.6891	Remote Similarity	NPD709	Approved
0.6885	Remote Similarity	NPD1751	Approved
0.6885	Remote Similarity	NPD3095	Discontinued
0.6885	Remote Similarity	NPD4589	Approved
0.687	Remote Similarity	NPD74	Approved
0.687	Remote Similarity	NPD9266	Approved
0.687	Remote Similarity	NPD2684	Approved
0.686	Remote Similarity	NPD7330	Discontinued
0.686	Remote Similarity	NPD5304	Approved
0.686	Remote Similarity	NPD5303	Approved
0.685	Remote Similarity	NPD5736	Approved
0.6833	Remote Similarity	NPD9493	Approved
0.6832	Remote Similarity	NPD9089	Approved
0.6825	Remote Similarity	NPD4339	Clinical (unspecified phase)
0.681	Remote Similarity	NPD9380	Clinical (unspecified phase)
0.6807	Remote Similarity	NPD1476	Clinical (unspecified phase)
0.6783	Remote Similarity	NPD9267	Approved
0.6783	Remote Similarity	NPD9263	Approved
0.6783	Remote Similarity	NPD9264	Approved
0.678	Remote Similarity	NPD7843	Approved
0.6777	Remote Similarity	NPD7644	Approved
0.6769	Remote Similarity	NPD839	Approved
0.6769	Remote Similarity	NPD840	Approved
0.675	Remote Similarity	NPD7157	Approved
0.6748	Remote Similarity	NPD9381	Approved
0.6748	Remote Similarity	NPD9384	Approved
0.6746	Remote Similarity	NPD5310	Approved
0.6746	Remote Similarity	NPD5311	Approved
0.6733	Remote Similarity	NPD9093	Approved
0.6726	Remote Similarity	NPD5700	Clinical (unspecified phase)
0.6723	Remote Similarity	NPD5283	Phase 1
0.6721	Remote Similarity	NPD1759	Phase 1
0.672	Remote Similarity	NPD2235	Phase 2
0.672	Remote Similarity	NPD2231	Phase 2
0.6719	Remote Similarity	NPD2237	Approved
0.6716	Remote Similarity	NPD2935	Discontinued
0.6716	Remote Similarity	NPD6100	Approved
0.6716	Remote Similarity	NPD6099	Approved
0.6696	Remote Similarity	NPD1616	Discontinued
0.6694	Remote Similarity	NPD7636	Approved
0.6693	Remote Similarity	NPD1470	Approved
0.6693	Remote Similarity	NPD3053	Approved
0.6693	Remote Similarity	NPD3055	Approved
0.6667	Remote Similarity	NPD9622	Approved
0.6667	Remote Similarity	NPD1357	Approved
0.6667	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD9244	Approved
0.6667	Remote Similarity	NPD4235	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD1755	Approved
0.6641	Remote Similarity	NPD2195	Approved
0.6641	Remote Similarity	NPD2194	Approved
0.6641	Remote Similarity	NPD4624	Approved
0.6641	Remote Similarity	NPD6663	Approved
0.6641	Remote Similarity	NPD6584	Phase 3
0.6639	Remote Similarity	NPD16	Approved
0.6639	Remote Similarity	NPD1758	Phase 1
0.6639	Remote Similarity	NPD821	Approved
0.6639	Remote Similarity	NPD856	Approved
0.6638	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.6637	Remote Similarity	NPD4818	Approved
0.6637	Remote Similarity	NPD4817	Approved
0.6617	Remote Similarity	NPD4097	Suspended
0.6615	Remote Similarity	NPD3027	Phase 3
0.6613	Remote Similarity	NPD5238	Clinical (unspecified phase)
0.6613	Remote Similarity	NPD2667	Approved
0.6613	Remote Similarity	NPD2668	Approved
0.6612	Remote Similarity	NPD255	Approved
0.6612	Remote Similarity	NPD256	Approved
0.6591	Remote Similarity	NPD2238	Phase 2
0.6591	Remote Similarity	NPD4060	Phase 1
0.6589	Remote Similarity	NPD3636	Approved
0.6589	Remote Similarity	NPD3637	Approved
0.6589	Remote Similarity	NPD3635	Approved
0.6585	Remote Similarity	NPD1548	Phase 1
0.656	Remote Similarity	NPD3143	Discontinued
0.656	Remote Similarity	NPD3026	Approved
0.656	Remote Similarity	NPD3023	Approved
0.6552	Remote Similarity	NPD3134	Approved
0.6538	Remote Similarity	NPD2606	Approved
0.6538	Remote Similarity	NPD4908	Phase 1
0.6538	Remote Similarity	NPD2605	Approved
0.6538	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6532	Remote Similarity	NPD1651	Approved
0.6532	Remote Similarity	NPD3025	Approved
0.6532	Remote Similarity	NPD3024	Approved
0.6532	Remote Similarity	NPD5585	Approved
0.6529	Remote Similarity	NPD475	Phase 2
0.6525	Remote Similarity	NPD6090	Discontinued
0.6525	Remote Similarity	NPD5451	Approved
0.6522	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6519	Remote Similarity	NPD3299	Clinical (unspecified phase)
0.6512	Remote Similarity	NPD859	Approved
0.6512	Remote Similarity	NPD858	Approved
0.6512	Remote Similarity	NPD599	Approved
0.6512	Remote Similarity	NPD9620	Approved
0.6512	Remote Similarity	NPD602	Approved
0.6512	Remote Similarity	NPD9621	Approved
0.6512	Remote Similarity	NPD9619	Approved
0.6508	Remote Similarity	NPD1610	Phase 2
0.6508	Remote Similarity	NPD1535	Discovery
0.6508	Remote Similarity	NPD1091	Approved
0.6508	Remote Similarity	NPD422	Phase 1
0.6504	Remote Similarity	NPD318	Approved
0.6504	Remote Similarity	NPD317	Approved
0.65	Remote Similarity	NPD1138	Approved
0.6496	Remote Similarity	NPD4257	Approved
0.6496	Remote Similarity	NPD4256	Phase 2

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