NPASS Compound

Structure

NPC177967 OpenBabel07101719242D 30 31 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 6.0622 -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 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 6.0622 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 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 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 6.9282 -0.0000 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 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 6.0622 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 2.5981 -2.5000 0.0000 O 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 -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 29 1 0 0 0 0 2 30 1 0 0 0 0 3 7 2 0 0 0 0 3 9 1 0 0 0 0 4 7 1 0 0 0 0 4 10 2 0 0 0 0 5 8 2 0 0 0 0 5 11 1 0 0 0 0 6 8 1 0 0 0 0 6 12 2 0 0 0 0 7 13 1 0 0 0 0 8 15 1 0 0 0 0 9 16 2 0 0 0 0 9 20 1 0 0 0 0 10 16 1 0 0 0 0 10 21 1 0 0 0 0 11 17 2 0 0 0 0 11 22 1 0 0 0 0 12 17 1 0 0 0 0 12 23 1 0 0 0 0 13 14 2 3 0 0 0 13 18 1 0 0 0 0 14 15 1 0 0 0 0 14 19 1 0 0 0 0 15 24 2 0 0 0 0 16 25 1 0 0 0 0 17 26 1 0 0 0 0 18 27 2 0 0 0 0 18 29 1 0 0 0 0 19 28 2 0 0 0 0 19 30 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	667.73
Volume:	432.369
LogP:	4.525
LogD:	2.1
LogS:	-4.655
# Rotatable Bonds:	7
TPSA:	110.13
# H-Bond Aceptor:	7
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	11

MedChem Properties

QED Drug-Likeness Score:	0.149
Synthetic Accessibility Score:	3.087
Fsp3:	0.105
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	2
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.093
MDCK Permeability:	1.878106741060037e-05
Pgp-inhibitor:	0.999
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.707
20% Bioavailability (F20%):	0.051
30% Bioavailability (F30%):	0.879

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.002
Plasma Protein Binding (PPB):	102.56169891357422%
Volume Distribution (VD):	0.324
Pgp-substrate:	3.308260440826416%

ADMET: Metabolism

CYP1A2-inhibitor:	0.897
CYP1A2-substrate:	0.188
CYP2C19-inhibitor:	0.817
CYP2C19-substrate:	0.07
CYP2C9-inhibitor:	0.868
CYP2C9-substrate:	0.466
CYP2D6-inhibitor:	0.473
CYP2D6-substrate:	0.153
CYP3A4-inhibitor:	0.187
CYP3A4-substrate:	0.075

ADMET: Excretion

Clearance (CL):	0.31
Half-life (T1/2):	0.404

ADMET: Toxicity

hERG Blockers:	0.387
Human Hepatotoxicity (H-HT):	0.287
Drug-inuced Liver Injury (DILI):	0.965
AMES Toxicity:	0.031
Rat Oral Acute Toxicity:	0.232
Maximum Recommended Daily Dose:	0.676
Skin Sensitization:	0.118
Carcinogencity:	0.041
Eye Corrosion:	0.003
Eye Irritation:	0.3
Respiratory Toxicity:	0.03

Download Data

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

Natural Product: NPC177967

Natural Product ID:	NPC177967
*Common Name:**	Z/E-Synoilide A
IUPAC Name:	dimethyl 2-(3,5-dibromo-4-hydroxybenzoyl)-3-(3,5-dibromo-4-hydroxyphenyl)but-2-enedioate
Synonyms:	Z/E-Synoilide A
Standard InCHIKey:	WOJXBWZIOKWNOU-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C19H12Br4O7/c1-29-18(27)13(7-3-9(20)16(25)10(21)4-7)14(19(28)30-2)15(24)8-5-11(22)17(26)12(23)6-8/h3-6,25-26H,1-2H3
SMILES:	COC(=O)C(=C(C(=O)c1cc(c(c(c1)Br)O)Br)C(=O)OC)c1cc(c(c(c1)Br)O)Br
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2204158
PubChem CID:	73352810
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	=	26300.0	nM	PMID[528497]
NPT81	Cell Line	A549	Homo sapiens	LC50	=	19200.0	nM	PMID[528497]
NPT111	Cell Line	K562	Homo sapiens	LC50	=	53700.0	nM	PMID[528497]
NPT2	Others	Unspecified		IC50	=	28000.0	nM	PMID[528497]
NPT2	Others	Unspecified		IC50	>	120000.0	nM	PMID[528497]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	>	100.0	ug.mL-1	PMID[528497]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	MIC	=	100.0	ug.mL-1	PMID[528497]
NPT1190	Organism	Salmonella enterica	Salmonella enterica	MIC	=	50.0	ug.mL-1	PMID[528497]
NPT3147	Organism	Kocuria rhizophila	Kocuria rhizophila	MIC	=	100.0	ug.mL-1	PMID[528497]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	MIC	=	50.0	ug.mL-1	PMID[528497]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	100.0	ug.mL-1	PMID[528497]

☑ 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 NPC177967 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	321
0.1-0.2	1994
0.2-0.3	5193
0.3-0.4	12398
0.4-0.5	6778
0.5-0.6	9125
0.6-0.7	6584
0.7-0.8	272
0.8-0.85	17
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	NPC471237
0.9771	High Similarity	NPC471236
0.9771	High Similarity	NPC197766
0.9338	High Similarity	NPC147137
0.9203	High Similarity	NPC270848
0.9203	High Similarity	NPC122599
0.9203	High Similarity	NPC272868
0.9085	High Similarity	NPC470710
0.8841	High Similarity	NPC81137
0.8421	Intermediate Similarity	NPC105999
0.8397	Intermediate Similarity	NPC180207
0.8222	Intermediate Similarity	NPC213414
0.8209	Intermediate Similarity	NPC116562
0.8182	Intermediate Similarity	NPC100395
0.8129	Intermediate Similarity	NPC11449
0.8074	Intermediate Similarity	NPC296202
0.8067	Intermediate Similarity	NPC73132
0.8067	Intermediate Similarity	NPC471235
0.8067	Intermediate Similarity	NPC235033
0.8	Intermediate Similarity	NPC7830
0.7929	Intermediate Similarity	NPC478071
0.7914	Intermediate Similarity	NPC159987
0.7914	Intermediate Similarity	NPC78061
0.7914	Intermediate Similarity	NPC122359
0.7817	Intermediate Similarity	NPC259017
0.781	Intermediate Similarity	NPC68167
0.7708	Intermediate Similarity	NPC471328
0.7692	Intermediate Similarity	NPC54543
0.7606	Intermediate Similarity	NPC2596
0.7574	Intermediate Similarity	NPC249435
0.7556	Intermediate Similarity	NPC128249
0.7556	Intermediate Similarity	NPC131192
0.7516	Intermediate Similarity	NPC178097
0.75	Intermediate Similarity	NPC116842
0.75	Intermediate Similarity	NPC135103
0.75	Intermediate Similarity	NPC473358
0.7481	Intermediate Similarity	NPC17525
0.7481	Intermediate Similarity	NPC23402
0.7445	Intermediate Similarity	NPC94298
0.7445	Intermediate Similarity	NPC27633
0.7444	Intermediate Similarity	NPC114682
0.7434	Intermediate Similarity	NPC271451
0.7417	Intermediate Similarity	NPC184632
0.7405	Intermediate Similarity	NPC226699
0.74	Intermediate Similarity	NPC19622
0.74	Intermediate Similarity	NPC112789
0.7397	Intermediate Similarity	NPC262359
0.7358	Intermediate Similarity	NPC474535
0.7353	Intermediate Similarity	NPC322197
0.7351	Intermediate Similarity	NPC275903
0.7348	Intermediate Similarity	NPC471495
0.7347	Intermediate Similarity	NPC212631
0.7347	Intermediate Similarity	NPC87231
0.7347	Intermediate Similarity	NPC257756
0.7347	Intermediate Similarity	NPC205468
0.7347	Intermediate Similarity	NPC129132
0.7343	Intermediate Similarity	NPC204579
0.7343	Intermediate Similarity	NPC110211
0.7343	Intermediate Similarity	NPC95309
0.7338	Intermediate Similarity	NPC97188
0.7338	Intermediate Similarity	NPC233282
0.7333	Intermediate Similarity	NPC11824
0.7328	Intermediate Similarity	NPC6984
0.7319	Intermediate Similarity	NPC311091
0.7319	Intermediate Similarity	NPC471033
0.7313	Intermediate Similarity	NPC268388
0.7312	Intermediate Similarity	NPC475697
0.7305	Intermediate Similarity	NPC67300
0.7299	Intermediate Similarity	NPC19290
0.7299	Intermediate Similarity	NPC128825
0.7299	Intermediate Similarity	NPC83718
0.7297	Intermediate Similarity	NPC263670
0.7297	Intermediate Similarity	NPC192304
0.7297	Intermediate Similarity	NPC337373
0.7297	Intermediate Similarity	NPC139813
0.7297	Intermediate Similarity	NPC242294
0.7297	Intermediate Similarity	NPC56031
0.7297	Intermediate Similarity	NPC472365
0.7297	Intermediate Similarity	NPC175098
0.7297	Intermediate Similarity	NPC312318
0.7297	Intermediate Similarity	NPC188646
0.7293	Intermediate Similarity	NPC95172
0.7293	Intermediate Similarity	NPC88141
0.729	Intermediate Similarity	NPC469498
0.7279	Intermediate Similarity	NPC308037
0.7279	Intermediate Similarity	NPC64359
0.7279	Intermediate Similarity	NPC285350
0.7273	Intermediate Similarity	NPC293312
0.7273	Intermediate Similarity	NPC4164
0.7266	Intermediate Similarity	NPC61779
0.7261	Intermediate Similarity	NPC52931
0.726	Intermediate Similarity	NPC247779
0.7259	Intermediate Similarity	NPC17693
0.7248	Intermediate Similarity	NPC286336
0.7246	Intermediate Similarity	NPC469954
0.7241	Intermediate Similarity	NPC214553
0.7241	Intermediate Similarity	NPC221777
0.7241	Intermediate Similarity	NPC95537
0.7239	Intermediate Similarity	NPC183700
0.7237	Intermediate Similarity	NPC250597
0.7234	Intermediate Similarity	NPC73532
0.7234	Intermediate Similarity	NPC224273
0.7234	Intermediate Similarity	NPC143427
0.7234	Intermediate Similarity	NPC267552
0.7234	Intermediate Similarity	NPC19174
0.7234	Intermediate Similarity	NPC115159
0.7234	Intermediate Similarity	NPC45438
0.7229	Intermediate Similarity	NPC470566
0.7222	Intermediate Similarity	NPC473751
0.7208	Intermediate Similarity	NPC66593
0.7206	Intermediate Similarity	NPC471488
0.7203	Intermediate Similarity	NPC184219
0.72	Intermediate Similarity	NPC156092
0.72	Intermediate Similarity	NPC131039
0.7197	Intermediate Similarity	NPC95178
0.7197	Intermediate Similarity	NPC29989
0.7197	Intermediate Similarity	NPC17600
0.7197	Intermediate Similarity	NPC69332
0.7197	Intermediate Similarity	NPC70843
0.7194	Intermediate Similarity	NPC474890
0.7194	Intermediate Similarity	NPC161943
0.7194	Intermediate Similarity	NPC94637
0.7194	Intermediate Similarity	NPC273282
0.7192	Intermediate Similarity	NPC476119
0.7186	Intermediate Similarity	NPC470567
0.7185	Intermediate Similarity	NPC212718
0.7183	Intermediate Similarity	NPC133909
0.7183	Intermediate Similarity	NPC139171
0.7183	Intermediate Similarity	NPC32032
0.7183	Intermediate Similarity	NPC475192
0.7181	Intermediate Similarity	NPC28753
0.7181	Intermediate Similarity	NPC144051
0.7181	Intermediate Similarity	NPC159623
0.7181	Intermediate Similarity	NPC294593
0.7181	Intermediate Similarity	NPC18877
0.7181	Intermediate Similarity	NPC204960
0.7181	Intermediate Similarity	NPC82225
0.7181	Intermediate Similarity	NPC20560
0.7172	Intermediate Similarity	NPC266689
0.7172	Intermediate Similarity	NPC23126
0.7172	Intermediate Similarity	NPC98254
0.7172	Intermediate Similarity	NPC72158
0.7172	Intermediate Similarity	NPC100067
0.7172	Intermediate Similarity	NPC103356
0.7172	Intermediate Similarity	NPC105157
0.7172	Intermediate Similarity	NPC190043
0.7172	Intermediate Similarity	NPC30501
0.7172	Intermediate Similarity	NPC169250
0.7172	Intermediate Similarity	NPC162612
0.7172	Intermediate Similarity	NPC121104
0.717	Intermediate Similarity	NPC11892
0.7163	Intermediate Similarity	NPC471486
0.7163	Intermediate Similarity	NPC297186
0.7162	Intermediate Similarity	NPC112192
0.7162	Intermediate Similarity	NPC309717
0.7162	Intermediate Similarity	NPC313618
0.7162	Intermediate Similarity	NPC66384
0.7162	Intermediate Similarity	NPC189106
0.7162	Intermediate Similarity	NPC128348
0.7162	Intermediate Similarity	NPC164236
0.7162	Intermediate Similarity	NPC474135
0.7153	Intermediate Similarity	NPC49938
0.7153	Intermediate Similarity	NPC81808
0.7152	Intermediate Similarity	NPC249606
0.7152	Intermediate Similarity	NPC1486
0.7152	Intermediate Similarity	NPC274109
0.7152	Intermediate Similarity	NPC41461
0.7152	Intermediate Similarity	NPC25287
0.7152	Intermediate Similarity	NPC472367
0.7152	Intermediate Similarity	NPC213603
0.7152	Intermediate Similarity	NPC98115
0.7152	Intermediate Similarity	NPC477244
0.7152	Intermediate Similarity	NPC472364
0.7152	Intermediate Similarity	NPC150399
0.7152	Intermediate Similarity	NPC186838
0.7152	Intermediate Similarity	NPC473391
0.7152	Intermediate Similarity	NPC66349
0.7152	Intermediate Similarity	NPC477242
0.7152	Intermediate Similarity	NPC477243
0.7152	Intermediate Similarity	NPC12165
0.7152	Intermediate Similarity	NPC168105
0.7152	Intermediate Similarity	NPC476333
0.7143	Intermediate Similarity	NPC158222
0.7143	Intermediate Similarity	NPC42292
0.7143	Intermediate Similarity	NPC470987
0.7143	Intermediate Similarity	NPC90522
0.7143	Intermediate Similarity	NPC141523
0.7143	Intermediate Similarity	NPC307732
0.7143	Intermediate Similarity	NPC328459
0.7143	Intermediate Similarity	NPC29883
0.7143	Intermediate Similarity	NPC66905
0.7143	Intermediate Similarity	NPC21378
0.7133	Intermediate Similarity	NPC103842
0.7133	Intermediate Similarity	NPC14141
0.7133	Intermediate Similarity	NPC470210
0.7124	Intermediate Similarity	NPC470986
0.7124	Intermediate Similarity	NPC168471
0.7123	Intermediate Similarity	NPC293453
0.7123	Intermediate Similarity	NPC21305
0.7123	Intermediate Similarity	NPC79332

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 NPC177967 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	292
0.1-0.2	1032
0.2-0.3	1683
0.3-0.4	2999
0.4-0.5	2090
0.5-0.6	850
0.6-0.7	194
0.7-0.8	10
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
0.8039	Intermediate Similarity	NPD2296	Approved
0.7445	Intermediate Similarity	NPD9545	Approved
0.7368	Intermediate Similarity	NPD4287	Approved
0.731	Intermediate Similarity	NPD9718	Approved
0.7299	Intermediate Similarity	NPD9493	Approved
0.725	Intermediate Similarity	NPD4288	Approved
0.7162	Intermediate Similarity	NPD1240	Approved
0.7152	Intermediate Similarity	NPD2935	Discontinued
0.7143	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD3269	Clinical (unspecified phase)
0.7067	Intermediate Similarity	NPD1607	Approved
0.7063	Intermediate Similarity	NPD3972	Approved
0.7034	Intermediate Similarity	NPD1203	Approved
0.7027	Intermediate Similarity	NPD3764	Approved
0.7013	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.6993	Remote Similarity	NPD2344	Approved
0.6974	Remote Similarity	NPD1510	Phase 2
0.6974	Remote Similarity	NPD2799	Discontinued
0.6918	Remote Similarity	NPD1164	Approved
0.6913	Remote Similarity	NPD2313	Discontinued
0.6901	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.6859	Remote Similarity	NPD4628	Phase 3
0.6839	Remote Similarity	NPD1549	Phase 2
0.6839	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6838	Remote Similarity	NPD74	Approved
0.6838	Remote Similarity	NPD9266	Approved
0.6835	Remote Similarity	NPD6799	Approved
0.6828	Remote Similarity	NPD9717	Approved
0.6815	Remote Similarity	NPD2309	Approved
0.6813	Remote Similarity	NPD5586	Clinical (unspecified phase)
0.6779	Remote Similarity	NPD6832	Phase 2
0.6776	Remote Similarity	NPD230	Phase 1
0.6774	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD9267	Approved
0.6765	Remote Similarity	NPD9264	Approved
0.6765	Remote Similarity	NPD9263	Approved
0.6757	Remote Similarity	NPD2798	Approved
0.6748	Remote Similarity	NPD7411	Suspended
0.6735	Remote Similarity	NPD1876	Approved
0.6713	Remote Similarity	NPD1894	Discontinued
0.6712	Remote Similarity	NPD1481	Phase 2
0.6711	Remote Similarity	NPD943	Approved
0.6709	Remote Similarity	NPD2354	Approved
0.6687	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6687	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD2346	Discontinued
0.6647	Remote Similarity	NPD7075	Discontinued
0.6646	Remote Similarity	NPD3750	Approved
0.6646	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6645	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.6644	Remote Similarity	NPD1535	Discovery
0.6626	Remote Similarity	NPD7458	Discontinued
0.6617	Remote Similarity	NPD1238	Approved
0.6603	Remote Similarity	NPD5405	Approved
0.6603	Remote Similarity	NPD5406	Approved
0.6603	Remote Similarity	NPD1551	Phase 2
0.6603	Remote Similarity	NPD5408	Approved
0.6603	Remote Similarity	NPD5404	Approved
0.6596	Remote Similarity	NPD1241	Discontinued
0.6585	Remote Similarity	NPD6599	Discontinued
0.6579	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6579	Remote Similarity	NPD3268	Approved
0.6577	Remote Similarity	NPD1470	Approved
0.6575	Remote Similarity	NPD3847	Discontinued
0.6573	Remote Similarity	NPD405	Clinical (unspecified phase)
0.6566	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6566	Remote Similarity	NPD7819	Suspended
0.6561	Remote Similarity	NPD2353	Approved
0.6561	Remote Similarity	NPD2355	Clinical (unspecified phase)
0.6554	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6549	Remote Similarity	NPD9281	Approved
0.6544	Remote Similarity	NPD1237	Approved
0.6541	Remote Similarity	NPD7003	Approved
0.6538	Remote Similarity	NPD4308	Phase 3
0.6531	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6531	Remote Similarity	NPD1201	Approved
0.6516	Remote Similarity	NPD6651	Approved
0.651	Remote Similarity	NPD1283	Approved
0.6506	Remote Similarity	NPD6801	Discontinued
0.65	Remote Similarity	NPD3887	Approved
0.6497	Remote Similarity	NPD2796	Approved
0.6491	Remote Similarity	NPD1161	Approved
0.649	Remote Similarity	NPD9494	Approved
0.6489	Remote Similarity	NPD1202	Approved
0.6486	Remote Similarity	NPD9269	Phase 2
0.6486	Remote Similarity	NPD1608	Approved
0.6485	Remote Similarity	NPD4380	Phase 2
0.6475	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD1930	Approved
0.6471	Remote Similarity	NPD1929	Approved
0.6471	Remote Similarity	NPD9261	Approved
0.6471	Remote Similarity	NPD1931	Clinical (unspecified phase)
0.6467	Remote Similarity	NPD2797	Approved
0.646	Remote Similarity	NPD7440	Discontinued
0.6456	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6452	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6452	Remote Similarity	NPD1933	Approved
0.645	Remote Similarity	NPD3749	Approved
0.6439	Remote Similarity	NPD2933	Approved
0.6439	Remote Similarity	NPD2934	Approved
0.6438	Remote Similarity	NPD8166	Discontinued
0.6438	Remote Similarity	NPD9268	Approved
0.6429	Remote Similarity	NPD520	Approved
0.6424	Remote Similarity	NPD3455	Phase 2
0.6424	Remote Similarity	NPD3226	Approved
0.6423	Remote Similarity	NPD164	Approved
0.642	Remote Similarity	NPD1511	Approved
0.642	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6416	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6407	Remote Similarity	NPD1934	Approved
0.6398	Remote Similarity	NPD6190	Approved
0.6391	Remote Similarity	NPD3882	Suspended
0.6391	Remote Similarity	NPD2859	Approved
0.6391	Remote Similarity	NPD7768	Phase 2
0.6391	Remote Similarity	NPD2860	Approved
0.6385	Remote Similarity	NPD9258	Approved
0.6385	Remote Similarity	NPD9256	Approved
0.638	Remote Similarity	NPD2533	Approved
0.638	Remote Similarity	NPD2532	Approved
0.638	Remote Similarity	NPD2534	Approved
0.6375	Remote Similarity	NPD1243	Approved
0.6375	Remote Similarity	NPD2800	Approved
0.6369	Remote Similarity	NPD2801	Approved
0.6369	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD411	Approved
0.6364	Remote Similarity	NPD6798	Discontinued
0.6358	Remote Similarity	NPD3267	Approved
0.6358	Remote Similarity	NPD3266	Approved
0.6357	Remote Similarity	NPD2182	Approved
0.6353	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6346	Remote Similarity	NPD447	Suspended
0.6341	Remote Similarity	NPD5049	Phase 3
0.6341	Remote Similarity	NPD1512	Approved
0.6331	Remote Similarity	NPD3817	Phase 2
0.6331	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6329	Remote Similarity	NPD7033	Discontinued
0.6329	Remote Similarity	NPD3748	Approved
0.6323	Remote Similarity	NPD6233	Phase 2
0.6323	Remote Similarity	NPD4062	Phase 3
0.6319	Remote Similarity	NPD7390	Discontinued
0.6319	Remote Similarity	NPD5951	Approved
0.6319	Remote Similarity	NPD690	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD1019	Discontinued
0.6309	Remote Similarity	NPD1281	Approved
0.6309	Remote Similarity	NPD6287	Discontinued
0.6304	Remote Similarity	NPD5909	Discontinued
0.6304	Remote Similarity	NPD9244	Approved
0.6303	Remote Similarity	NPD5403	Approved
0.6303	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6301	Remote Similarity	NPD6232	Discontinued
0.6301	Remote Similarity	NPD5536	Phase 2
0.6299	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6294	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6291	Remote Similarity	NPD3225	Approved
0.6286	Remote Similarity	NPD7473	Discontinued
0.6284	Remote Similarity	NPD17	Approved
0.6282	Remote Similarity	NPD3142	Approved
0.6282	Remote Similarity	NPD4307	Phase 2
0.6282	Remote Similarity	NPD3140	Approved
0.6282	Remote Similarity	NPD4445	Approved
0.628	Remote Similarity	NPD5401	Approved
0.6276	Remote Similarity	NPD256	Approved
0.6276	Remote Similarity	NPD255	Approved
0.6268	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6259	Remote Similarity	NPD5048	Discontinued
0.625	Remote Similarity	NPD1471	Phase 3
0.625	Remote Similarity	NPD3020	Approved
0.625	Remote Similarity	NPD2066	Phase 3
0.6242	Remote Similarity	NPD6273	Approved
0.6242	Remote Similarity	NPD6355	Discontinued
0.6236	Remote Similarity	NPD5953	Discontinued
0.6226	Remote Similarity	NPD651	Clinical (unspecified phase)
0.6224	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.6221	Remote Similarity	NPD1168	Approved
0.6215	Remote Similarity	NPD7286	Phase 2
0.6214	Remote Similarity	NPD3134	Approved
0.6205	Remote Similarity	NPD920	Approved
0.6194	Remote Similarity	NPD7008	Discontinued
0.6181	Remote Similarity	NPD5535	Approved
0.6174	Remote Similarity	NPD2932	Approved
0.6174	Remote Similarity	NPD3019	Approved
0.617	Remote Similarity	NPD1358	Approved
0.6159	Remote Similarity	NPD1932	Approved
0.6159	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6145	Remote Similarity	NPD9509	Clinical (unspecified phase)
0.6129	Remote Similarity	NPD2614	Approved
0.6122	Remote Similarity	NPD9568	Approved
0.6118	Remote Similarity	NPD7577	Discontinued
0.6115	Remote Similarity	NPD6663	Approved
0.6114	Remote Similarity	NPD6808	Phase 2
0.6107	Remote Similarity	NPD1651	Approved
0.6104	Remote Similarity	NPD5647	Approved
0.6104	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6093	Remote Similarity	NPD422	Phase 1
0.6087	Remote Similarity	NPD4477	Approved
0.6087	Remote Similarity	NPD4476	Approved
0.6084	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6084	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6077	Remote Similarity	NPD9257	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