NPASS Compound

Structure

NPC197766 OpenBabel07101718282D 29 30 0 0 0 0 0 0 0 0999 V2000 5.1962 -4.0000 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 5.1962 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -1.5000 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 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 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 6.9282 -0.0000 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 3.4641 -1.0000 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 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -2.5000 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 7.7942 -1.5000 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -2.5000 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 3.4641 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 28 1 0 0 0 0 2 29 1 0 0 0 0 3 4 2 0 0 0 0 3 8 1 0 0 0 0 4 13 1 0 0 0 0 5 8 2 0 0 0 0 5 10 1 0 0 0 0 6 9 2 0 0 0 0 6 11 1 0 0 0 0 7 9 1 0 0 0 0 7 12 2 0 0 0 0 8 14 1 0 0 0 0 9 16 1 0 0 0 0 10 13 2 0 0 0 0 10 20 1 0 0 0 0 11 17 2 0 0 0 0 11 21 1 0 0 0 0 12 17 1 0 0 0 0 12 22 1 0 0 0 0 13 23 1 0 0 0 0 14 15 2 3 0 0 0 14 18 1 0 0 0 0 15 16 1 0 0 0 0 15 19 1 0 0 0 0 16 24 2 0 0 0 0 17 25 1 0 0 0 0 18 26 2 0 0 0 0 18 28 1 0 0 0 0 19 27 2 0 0 0 0 19 29 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	589.82
Volume:	413.085
LogP:	4.143
LogD:	2.145
LogS:	-4.664
# Rotatable Bonds:	7
TPSA:	110.13
# H-Bond Aceptor:	7
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	10

MedChem Properties

QED Drug-Likeness Score:	0.174
Synthetic Accessibility Score:	2.95
Fsp3:	0.105
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.929
MDCK Permeability:	1.735704245220404e-05
Pgp-inhibitor:	0.998
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.56
20% Bioavailability (F20%):	0.023
30% Bioavailability (F30%):	0.857

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.006
Plasma Protein Binding (PPB):	101.5385971069336%
Volume Distribution (VD):	0.387
Pgp-substrate:	1.7578691244125366%

ADMET: Metabolism

CYP1A2-inhibitor:	0.935
CYP1A2-substrate:	0.222
CYP2C19-inhibitor:	0.902
CYP2C19-substrate:	0.063
CYP2C9-inhibitor:	0.883
CYP2C9-substrate:	0.733
CYP2D6-inhibitor:	0.814
CYP2D6-substrate:	0.183
CYP3A4-inhibitor:	0.307
CYP3A4-substrate:	0.105

ADMET: Excretion

Clearance (CL):	0.522
Half-life (T1/2):	0.498

ADMET: Toxicity

hERG Blockers:	0.218
Human Hepatotoxicity (H-HT):	0.264
Drug-inuced Liver Injury (DILI):	0.975
AMES Toxicity:	0.044
Rat Oral Acute Toxicity:	0.158
Maximum Recommended Daily Dose:	0.559
Skin Sensitization:	0.095
Carcinogencity:	0.042
Eye Corrosion:	0.003
Eye Irritation:	0.468
Respiratory Toxicity:	0.027

Download Data

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

Natural Product: NPC197766

Natural Product ID:	NPC197766
*Common Name:**	Z/E-Synoilide B
IUPAC Name:	dimethyl 2-(3-bromo-4-hydroxyphenyl)-3-(3,5-dibromo-4-hydroxybenzoyl)but-2-enedioate
Synonyms:	Z/E-Synoilide B
Standard InCHIKey:	GMHLSOYTFNFLNQ-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C19H13Br3O7/c1-28-18(26)14(8-3-4-13(23)10(20)5-8)15(19(27)29-2)16(24)9-6-11(21)17(25)12(22)7-9/h3-7,23,25H,1-2H3
SMILES:	COC(=O)C(=C(C(=O)c1cc(c(c(c1)Br)O)Br)C(=O)OC)c1ccc(c(c1)Br)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2204159
PubChem CID:	73352811
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0003467] Linear 1,3-diarylpropanoids [CHEMONTID:0001630] Chalcones and dihydrochalcones [CHEMONTID:0003474] Retrochalcones

*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
NPO33080	synoicum sp.	Species	Polyclinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[22652254]
NPO33080	synoicum sp.	Species	Polyclinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[23145909]
NPO33080	synoicum sp.	Species	Polyclinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[23747224]

☑ 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
MIC	6
Others	2

Activity Type	# Activity
Cell Line	2
Individual Protein	1
NON-MOLECULAR	2
Organism	4
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1087	Individual Protein	Isocitrate lyase	Candida albicans	IC50	=	47600.0	nM	PMID[451186]
NPT81	Cell Line	A549	Homo sapiens	LC50	>	100000.0	nM	PMID[451186]
NPT111	Cell Line	K562	Homo sapiens	LC50	=	49700.0	nM	PMID[451186]
NPT2	Others	Unspecified		IC50	=	145400.0	nM	PMID[451186]
NPT2	Others	Unspecified		IC50	>	120000.0	nM	PMID[451186]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	>	100.0	ug.mL-1	PMID[451186]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	MIC	>	100.0	ug.mL-1	PMID[451186]
NPT1190	Organism	Salmonella enterica	Salmonella enterica	MIC	>	100.0	ug.mL-1	PMID[451186]
NPT3147	Organism	Kocuria rhizophila	Kocuria rhizophila	MIC	>	100.0	ug.mL-1	PMID[451186]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	>	100.0	ug.mL-1	PMID[451186]

☑ 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 NPC197766 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	323
0.1-0.2	2019
0.2-0.3	5070
0.3-0.4	12203
0.4-0.5	6368
0.5-0.6	8647
0.6-0.7	7530
0.7-0.8	500
0.8-0.85	22
0.85-0.9	6
0.9-0.95	5
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC471236
0.9771	High Similarity	NPC471237
0.9771	High Similarity	NPC177967
0.9275	High Similarity	NPC270848
0.9275	High Similarity	NPC272868
0.9275	High Similarity	NPC122599
0.9155	High Similarity	NPC470710
0.913	High Similarity	NPC147137
0.8643	High Similarity	NPC81137
0.8433	Intermediate Similarity	NPC213414
0.8333	Intermediate Similarity	NPC11449
0.8333	Intermediate Similarity	NPC180207
0.8284	Intermediate Similarity	NPC296202
0.8222	Intermediate Similarity	NPC105999
0.8209	Intermediate Similarity	NPC7830
0.8148	Intermediate Similarity	NPC116562
0.8133	Intermediate Similarity	NPC73132
0.8133	Intermediate Similarity	NPC471235
0.8133	Intermediate Similarity	NPC235033
0.8129	Intermediate Similarity	NPC478071
0.812	Intermediate Similarity	NPC100395
0.8116	Intermediate Similarity	NPC122359
0.8116	Intermediate Similarity	NPC159987
0.8116	Intermediate Similarity	NPC78061
0.8015	Intermediate Similarity	NPC68167
0.7801	Intermediate Similarity	NPC2596
0.7778	Intermediate Similarity	NPC249435
0.7778	Intermediate Similarity	NPC471328
0.7762	Intermediate Similarity	NPC259017
0.7761	Intermediate Similarity	NPC128249
0.7761	Intermediate Similarity	NPC131192
0.771	Intermediate Similarity	NPC473358
0.771	Intermediate Similarity	NPC116842
0.7692	Intermediate Similarity	NPC17525
0.7687	Intermediate Similarity	NPC23402
0.7652	Intermediate Similarity	NPC114682
0.7647	Intermediate Similarity	NPC94298
0.7647	Intermediate Similarity	NPC27633
0.7616	Intermediate Similarity	NPC271451
0.7615	Intermediate Similarity	NPC226699
0.7586	Intermediate Similarity	NPC262359
0.7584	Intermediate Similarity	NPC19622
0.7584	Intermediate Similarity	NPC112789
0.7582	Intermediate Similarity	NPC178097
0.7557	Intermediate Similarity	NPC471495
0.7556	Intermediate Similarity	NPC322197
0.7538	Intermediate Similarity	NPC6984
0.7537	Intermediate Similarity	NPC11824
0.7536	Intermediate Similarity	NPC233282
0.7535	Intermediate Similarity	NPC204579
0.7535	Intermediate Similarity	NPC110211
0.7535	Intermediate Similarity	NPC95309
0.7534	Intermediate Similarity	NPC212631
0.7534	Intermediate Similarity	NPC87231
0.7534	Intermediate Similarity	NPC257756
0.7534	Intermediate Similarity	NPC129132
0.7534	Intermediate Similarity	NPC205468
0.7533	Intermediate Similarity	NPC275903
0.7519	Intermediate Similarity	NPC268388
0.7518	Intermediate Similarity	NPC471033
0.7518	Intermediate Similarity	NPC311091
0.7516	Intermediate Similarity	NPC97188
0.75	Intermediate Similarity	NPC88141
0.75	Intermediate Similarity	NPC54543
0.75	Intermediate Similarity	NPC67300
0.75	Intermediate Similarity	NPC19290
0.75	Intermediate Similarity	NPC95172
0.75	Intermediate Similarity	NPC128825
0.7483	Intermediate Similarity	NPC337373
0.7483	Intermediate Similarity	NPC312318
0.7483	Intermediate Similarity	NPC184632
0.7483	Intermediate Similarity	NPC175098
0.7483	Intermediate Similarity	NPC56031
0.7483	Intermediate Similarity	NPC263670
0.7483	Intermediate Similarity	NPC242294
0.7483	Intermediate Similarity	NPC472365
0.7483	Intermediate Similarity	NPC188646
0.7483	Intermediate Similarity	NPC192304
0.7483	Intermediate Similarity	NPC139813
0.7481	Intermediate Similarity	NPC285350
0.7468	Intermediate Similarity	NPC469498
0.7466	Intermediate Similarity	NPC308037
0.7466	Intermediate Similarity	NPC64359
0.7465	Intermediate Similarity	NPC4164
0.7464	Intermediate Similarity	NPC61779
0.7463	Intermediate Similarity	NPC17693
0.7452	Intermediate Similarity	NPC135103
0.7448	Intermediate Similarity	NPC247779
0.7445	Intermediate Similarity	NPC469954
0.7444	Intermediate Similarity	NPC183700
0.7436	Intermediate Similarity	NPC52931
0.7432	Intermediate Similarity	NPC286336
0.7431	Intermediate Similarity	NPC95537
0.7431	Intermediate Similarity	NPC221777
0.7429	Intermediate Similarity	NPC224273
0.7429	Intermediate Similarity	NPC45438
0.7429	Intermediate Similarity	NPC143427
0.7429	Intermediate Similarity	NPC19174
0.7429	Intermediate Similarity	NPC73532
0.7429	Intermediate Similarity	NPC267552
0.7429	Intermediate Similarity	NPC115159
0.7421	Intermediate Similarity	NPC474535
0.7413	Intermediate Similarity	NPC473751
0.7405	Intermediate Similarity	NPC29989
0.7405	Intermediate Similarity	NPC70843
0.7405	Intermediate Similarity	NPC69332
0.7405	Intermediate Similarity	NPC95178
0.7394	Intermediate Similarity	NPC184219
0.7391	Intermediate Similarity	NPC474890
0.7391	Intermediate Similarity	NPC161943
0.7391	Intermediate Similarity	NPC273282
0.7391	Intermediate Similarity	NPC94637
0.7388	Intermediate Similarity	NPC212718
0.7386	Intermediate Similarity	NPC66593
0.7383	Intermediate Similarity	NPC131039
0.7376	Intermediate Similarity	NPC32032
0.7376	Intermediate Similarity	NPC133909
0.7376	Intermediate Similarity	NPC139171
0.7375	Intermediate Similarity	NPC475697
0.7372	Intermediate Similarity	NPC17600
0.7365	Intermediate Similarity	NPC82225
0.7365	Intermediate Similarity	NPC20560
0.7365	Intermediate Similarity	NPC294593
0.7365	Intermediate Similarity	NPC18877
0.7365	Intermediate Similarity	NPC144051
0.7365	Intermediate Similarity	NPC204960
0.7365	Intermediate Similarity	NPC28753
0.7365	Intermediate Similarity	NPC159623
0.7361	Intermediate Similarity	NPC98254
0.7361	Intermediate Similarity	NPC72158
0.7361	Intermediate Similarity	NPC30501
0.7361	Intermediate Similarity	NPC169250
0.7361	Intermediate Similarity	NPC190043
0.7361	Intermediate Similarity	NPC23126
0.7361	Intermediate Similarity	NPC100067
0.7361	Intermediate Similarity	NPC266689
0.7361	Intermediate Similarity	NPC162612
0.7361	Intermediate Similarity	NPC105157
0.7361	Intermediate Similarity	NPC103356
0.7357	Intermediate Similarity	NPC297186
0.7353	Intermediate Similarity	NPC81808
0.7348	Intermediate Similarity	NPC141523
0.7348	Intermediate Similarity	NPC29883
0.7347	Intermediate Similarity	NPC189106
0.7347	Intermediate Similarity	NPC309717
0.7347	Intermediate Similarity	NPC164236
0.7347	Intermediate Similarity	NPC66384
0.7347	Intermediate Similarity	NPC128348
0.7347	Intermediate Similarity	NPC313618
0.7347	Intermediate Similarity	NPC112192
0.7343	Intermediate Similarity	NPC49938
0.7342	Intermediate Similarity	NPC11892
0.7338	Intermediate Similarity	NPC90522
0.7338	Intermediate Similarity	NPC158222
0.7338	Intermediate Similarity	NPC328459
0.7333	Intermediate Similarity	NPC472364
0.7333	Intermediate Similarity	NPC477244
0.7333	Intermediate Similarity	NPC473391
0.7333	Intermediate Similarity	NPC249606
0.7333	Intermediate Similarity	NPC98115
0.7333	Intermediate Similarity	NPC66349
0.7333	Intermediate Similarity	NPC477243
0.7333	Intermediate Similarity	NPC186838
0.7333	Intermediate Similarity	NPC168105
0.7333	Intermediate Similarity	NPC150399
0.7333	Intermediate Similarity	NPC477242
0.7333	Intermediate Similarity	NPC12165
0.7333	Intermediate Similarity	NPC41461
0.7333	Intermediate Similarity	NPC274109
0.7333	Intermediate Similarity	NPC472367
0.7333	Intermediate Similarity	NPC25287
0.7333	Intermediate Similarity	NPC213603
0.7333	Intermediate Similarity	NPC1486
0.7333	Intermediate Similarity	NPC476333
0.7329	Intermediate Similarity	NPC307732
0.7329	Intermediate Similarity	NPC66905
0.7329	Intermediate Similarity	NPC42292
0.7324	Intermediate Similarity	NPC14141
0.7315	Intermediate Similarity	NPC470210
0.7313	Intermediate Similarity	NPC21162
0.731	Intermediate Similarity	NPC21305
0.731	Intermediate Similarity	NPC214553
0.731	Intermediate Similarity	NPC473744
0.731	Intermediate Similarity	NPC79332
0.731	Intermediate Similarity	NPC473017
0.731	Intermediate Similarity	NPC196034
0.7305	Intermediate Similarity	NPC242895
0.7305	Intermediate Similarity	NPC198336
0.7305	Intermediate Similarity	NPC156139
0.7303	Intermediate Similarity	NPC250597
0.7297	Intermediate Similarity	NPC43627
0.7293	Intermediate Similarity	NPC206341
0.7293	Intermediate Similarity	NPC224584
0.7292	Intermediate Similarity	NPC267846
0.7292	Intermediate Similarity	NPC62952
0.7289	Intermediate Similarity	NPC470566
0.7286	Intermediate Similarity	NPC159525
0.7286	Intermediate Similarity	NPC72977
0.7285	Intermediate Similarity	NPC303644
0.7285	Intermediate Similarity	NPC250266

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 NPC197766 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	293
0.1-0.2	1014
0.2-0.3	1580
0.3-0.4	2945
0.4-0.5	2091
0.5-0.6	969
0.6-0.7	238
0.7-0.8	19
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8224	Intermediate Similarity	NPD2296	Approved
0.7647	Intermediate Similarity	NPD9545	Approved
0.75	Intermediate Similarity	NPD9493	Approved
0.7421	Intermediate Similarity	NPD4288	Approved
0.7348	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7347	Intermediate Similarity	NPD1240	Approved
0.7333	Intermediate Similarity	NPD2935	Discontinued
0.7326	Intermediate Similarity	NPD4287	Approved
0.726	Intermediate Similarity	NPD9718	Approved
0.7254	Intermediate Similarity	NPD3972	Approved
0.7248	Intermediate Similarity	NPD1607	Approved
0.7241	Intermediate Similarity	NPD3269	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD1203	Approved
0.7211	Intermediate Similarity	NPD3764	Approved
0.719	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7171	Intermediate Similarity	NPD2344	Approved
0.7152	Intermediate Similarity	NPD1510	Phase 2
0.7152	Intermediate Similarity	NPD2799	Discontinued
0.7103	Intermediate Similarity	NPD1164	Approved
0.7037	Intermediate Similarity	NPD74	Approved
0.7037	Intermediate Similarity	NPD9266	Approved
0.7032	Intermediate Similarity	NPD4628	Phase 3
0.7014	Intermediate Similarity	NPD9717	Approved
0.7013	Intermediate Similarity	NPD1549	Phase 2
0.7006	Intermediate Similarity	NPD6799	Approved
0.6987	Remote Similarity	NPD2309	Approved
0.6981	Remote Similarity	NPD5586	Clinical (unspecified phase)
0.698	Remote Similarity	NPD2313	Discontinued
0.6963	Remote Similarity	NPD9264	Approved
0.6963	Remote Similarity	NPD9267	Approved
0.6963	Remote Similarity	NPD9263	Approved
0.6959	Remote Similarity	NPD6832	Phase 2
0.6948	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6948	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6939	Remote Similarity	NPD2798	Approved
0.6918	Remote Similarity	NPD1876	Approved
0.6914	Remote Similarity	NPD7411	Suspended
0.6903	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD1481	Phase 2
0.6887	Remote Similarity	NPD943	Approved
0.6879	Remote Similarity	NPD2354	Approved
0.6855	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6853	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD230	Phase 1
0.6828	Remote Similarity	NPD1535	Discovery
0.6815	Remote Similarity	NPD3750	Approved
0.6815	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6807	Remote Similarity	NPD7075	Discontinued
0.679	Remote Similarity	NPD7458	Discontinued
0.6786	Remote Similarity	NPD1241	Discontinued
0.6783	Remote Similarity	NPD1894	Discontinued
0.6774	Remote Similarity	NPD1551	Phase 2
0.6761	Remote Similarity	NPD405	Clinical (unspecified phase)
0.6759	Remote Similarity	NPD3847	Discontinued
0.6757	Remote Similarity	NPD1470	Approved
0.6755	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6755	Remote Similarity	NPD3268	Approved
0.675	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6748	Remote Similarity	NPD6599	Discontinued
0.6738	Remote Similarity	NPD9281	Approved
0.6735	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6731	Remote Similarity	NPD2353	Approved
0.6731	Remote Similarity	NPD2346	Discontinued
0.6731	Remote Similarity	NPD2355	Clinical (unspecified phase)
0.6727	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6727	Remote Similarity	NPD7819	Suspended
0.6712	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6712	Remote Similarity	NPD1201	Approved
0.671	Remote Similarity	NPD4308	Phase 3
0.671	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.6709	Remote Similarity	NPD7003	Approved
0.6692	Remote Similarity	NPD1238	Approved
0.6689	Remote Similarity	NPD1283	Approved
0.6667	Remote Similarity	NPD1608	Approved
0.6667	Remote Similarity	NPD2796	Approved
0.6667	Remote Similarity	NPD9261	Approved
0.6667	Remote Similarity	NPD5408	Approved
0.6667	Remote Similarity	NPD6801	Discontinued
0.6667	Remote Similarity	NPD3887	Approved
0.6667	Remote Similarity	NPD5404	Approved
0.6667	Remote Similarity	NPD5405	Approved
0.6667	Remote Similarity	NPD9494	Approved
0.6667	Remote Similarity	NPD5406	Approved
0.6646	Remote Similarity	NPD4380	Phase 2
0.6644	Remote Similarity	NPD2797	Approved
0.6641	Remote Similarity	NPD2934	Approved
0.6641	Remote Similarity	NPD2933	Approved
0.6625	Remote Similarity	NPD7440	Discontinued
0.6623	Remote Similarity	NPD1933	Approved
0.6623	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6618	Remote Similarity	NPD1237	Approved
0.6607	Remote Similarity	NPD3749	Approved
0.6604	Remote Similarity	NPD8166	Discontinued
0.6601	Remote Similarity	NPD520	Approved
0.6591	Remote Similarity	NPD2859	Approved
0.6591	Remote Similarity	NPD2860	Approved
0.6585	Remote Similarity	NPD3455	Phase 2
0.6585	Remote Similarity	NPD3226	Approved
0.6584	Remote Similarity	NPD1511	Approved
0.6584	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.657	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6566	Remote Similarity	NPD1934	Approved
0.6565	Remote Similarity	NPD1202	Approved
0.6562	Remote Similarity	NPD6190	Approved
0.6554	Remote Similarity	NPD9269	Phase 2
0.655	Remote Similarity	NPD1161	Approved
0.6548	Remote Similarity	NPD3882	Suspended
0.6548	Remote Similarity	NPD7768	Phase 2
0.6547	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6544	Remote Similarity	NPD1929	Approved
0.6544	Remote Similarity	NPD1930	Approved
0.6544	Remote Similarity	NPD1931	Clinical (unspecified phase)
0.6536	Remote Similarity	NPD6798	Discontinued
0.6536	Remote Similarity	NPD411	Approved
0.6533	Remote Similarity	NPD3267	Approved
0.6533	Remote Similarity	NPD3266	Approved
0.6527	Remote Similarity	NPD2801	Approved
0.6527	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6519	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6516	Remote Similarity	NPD447	Suspended
0.6509	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6507	Remote Similarity	NPD9268	Approved
0.6503	Remote Similarity	NPD1512	Approved
0.6497	Remote Similarity	NPD3748	Approved
0.6497	Remote Similarity	NPD7033	Discontinued
0.6496	Remote Similarity	NPD164	Approved
0.6494	Remote Similarity	NPD4062	Phase 3
0.6494	Remote Similarity	NPD6233	Phase 2
0.649	Remote Similarity	NPD1019	Discontinued
0.6488	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6488	Remote Similarity	NPD3817	Phase 2
0.6486	Remote Similarity	NPD1281	Approved
0.6483	Remote Similarity	NPD5536	Phase 2
0.6474	Remote Similarity	NPD6651	Approved
0.6467	Remote Similarity	NPD3225	Approved
0.6463	Remote Similarity	NPD17	Approved
0.6463	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6463	Remote Similarity	NPD5403	Approved
0.6462	Remote Similarity	NPD9256	Approved
0.6462	Remote Similarity	NPD9258	Approved
0.6458	Remote Similarity	NPD256	Approved
0.6458	Remote Similarity	NPD255	Approved
0.6453	Remote Similarity	NPD6232	Discontinued
0.6452	Remote Similarity	NPD4307	Phase 2
0.6452	Remote Similarity	NPD3140	Approved
0.6452	Remote Similarity	NPD3142	Approved
0.6444	Remote Similarity	NPD3020	Approved
0.6442	Remote Similarity	NPD5401	Approved
0.6438	Remote Similarity	NPD1243	Approved
0.6437	Remote Similarity	NPD7473	Discontinued
0.6429	Remote Similarity	NPD2182	Approved
0.6415	Remote Similarity	NPD1471	Phase 3
0.641	Remote Similarity	NPD6355	Discontinued
0.6403	Remote Similarity	NPD3134	Approved
0.6402	Remote Similarity	NPD5049	Phase 3
0.6402	Remote Similarity	NPD6273	Approved
0.6392	Remote Similarity	NPD651	Clinical (unspecified phase)
0.6389	Remote Similarity	NPD5951	Approved
0.6389	Remote Similarity	NPD690	Clinical (unspecified phase)
0.6384	Remote Similarity	NPD5953	Discontinued
0.638	Remote Similarity	NPD7390	Discontinued
0.6377	Remote Similarity	NPD5909	Discontinued
0.6376	Remote Similarity	NPD6287	Discontinued
0.6374	Remote Similarity	NPD1168	Approved
0.6364	Remote Similarity	NPD7286	Phase 2
0.6364	Remote Similarity	NPD5535	Approved
0.6364	Remote Similarity	NPD920	Approved
0.6364	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6357	Remote Similarity	NPD1358	Approved
0.6353	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6351	Remote Similarity	NPD2932	Approved
0.6351	Remote Similarity	NPD3019	Approved
0.6346	Remote Similarity	NPD4445	Approved
0.6341	Remote Similarity	NPD2534	Approved
0.6341	Remote Similarity	NPD2533	Approved
0.6341	Remote Similarity	NPD2532	Approved
0.6338	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6335	Remote Similarity	NPD2800	Approved
0.6331	Remote Similarity	NPD5048	Discontinued
0.6324	Remote Similarity	NPD2066	Phase 3
0.6319	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6303	Remote Similarity	NPD9509	Clinical (unspecified phase)
0.6301	Remote Similarity	NPD9568	Approved
0.6299	Remote Similarity	NPD2614	Approved
0.6294	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.6284	Remote Similarity	NPD1651	Approved
0.6282	Remote Similarity	NPD6663	Approved
0.6275	Remote Similarity	NPD5647	Approved
0.6272	Remote Similarity	NPD7577	Discontinued
0.6267	Remote Similarity	NPD422	Phase 1
0.6264	Remote Similarity	NPD6808	Phase 2
0.6259	Remote Similarity	NPD9244	Approved
0.6258	Remote Similarity	NPD7008	Discontinued
0.625	Remote Similarity	NPD4477	Approved
0.625	Remote Similarity	NPD4476	Approved
0.6242	Remote Similarity	NPD4626	Approved
0.6242	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6242	Remote Similarity	NPD2979	Phase 3
0.6235	Remote Similarity	NPD2976	Clinical (unspecified phase)
0.6234	Remote Similarity	NPD5736	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