NPASS Compound

Structure

NPC473094 OpenBabel07101719522D 34 37 0 0 1 0 0 0 0 0999 V2000 -3.8005 -2.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9345 -6.0827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4714 -2.6941 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6665 -6.0827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3364 -2.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2024 -4.0827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4742 -2.7988 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9345 -3.0827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2024 -3.0827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3364 -1.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4755 -2.8511 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0685 -4.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9282 -1.9078 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0685 -2.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9345 -4.0827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2024 -1.0827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0685 -1.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9309 -2.0125 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.3835 -1.0691 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.4067 -0.9135 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.8005 -4.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9945 -0.1045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3849 -1.1215 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.0215 -3.7421 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.9345 -1.0827 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0677 -2.0648 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.8375 -0.1781 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.6665 -4.0827 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6637 0.6386 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.9513 -0.2973 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.0685 -5.5827 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.9268 -1.8555 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.8005 -5.5827 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 8 1 0 0 0 0 2 31 1 0 0 0 0 3 32 1 0 0 0 0 4 33 1 0 0 0 0 5 9 2 0 0 0 0 5 10 1 0 0 0 0 6 9 1 0 0 0 0 6 12 2 0 0 0 0 7 11 1 0 0 0 0 7 13 2 0 0 0 0 8 14 1 0 0 0 0 8 15 2 0 0 0 0 9 14 1 0 0 0 0 10 16 2 0 0 0 0 11 18 1 0 0 0 0 11 24 2 0 0 0 0 12 15 1 0 0 0 0 12 31 1 0 0 0 0 13 19 1 0 0 0 0 13 32 1 0 0 0 0 14 17 2 0 0 0 0 15 21 1 0 0 0 0 16 17 1 0 0 0 0 16 22 1 0 0 0 0 17 25 1 0 0 0 0 18 23 1 6 0 0 0 18 26 1 0 0 0 0 19 23 1 6 0 0 0 19 27 1 0 0 0 0 20 10 1 6 0 0 0 20 23 1 0 0 0 0 20 34 1 0 0 0 0 21 28 2 0 0 0 0 21 33 1 0 0 0 0 22 29 2 0 0 0 0 22 34 1 0 0 0 0 23 30 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	474.12
Volume:	445.103
LogP:	2.178
LogD:	1.526
LogS:	-3.232
# Rotatable Bonds:	5
TPSA:	172.96
# H-Bond Aceptor:	11
# H-Bond Donor:	4
# Rings:	4
# Heavy Atoms:	11

MedChem Properties

QED Drug-Likeness Score:	0.4
Synthetic Accessibility Score:	4.532
Fsp3:	0.348
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-5.583
MDCK Permeability:	5.9996082200086676e-06
Pgp-inhibitor:	0.081
Pgp-substrate:	0.974
Human Intestinal Absorption (HIA):	0.808
20% Bioavailability (F20%):	0.4
30% Bioavailability (F30%):	0.082

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.028
Plasma Protein Binding (PPB):	85.08084869384766%
Volume Distribution (VD):	1.001
Pgp-substrate:	14.900249481201172%

ADMET: Metabolism

CYP1A2-inhibitor:	0.128
CYP1A2-substrate:	0.97
CYP2C19-inhibitor:	0.012
CYP2C19-substrate:	0.393
CYP2C9-inhibitor:	0.038
CYP2C9-substrate:	0.141
CYP2D6-inhibitor:	0.001
CYP2D6-substrate:	0.163
CYP3A4-inhibitor:	0.065
CYP3A4-substrate:	0.175

ADMET: Excretion

Clearance (CL):	4.776
Half-life (T1/2):	0.5

ADMET: Toxicity

hERG Blockers:	0.001
Human Hepatotoxicity (H-HT):	0.365
Drug-inuced Liver Injury (DILI):	0.975
AMES Toxicity:	0.091
Rat Oral Acute Toxicity:	0.818
Maximum Recommended Daily Dose:	0.171
Skin Sensitization:	0.05
Carcinogencity:	0.029
Eye Corrosion:	0.003
Eye Irritation:	0.039
Respiratory Toxicity:	0.132

Download Data

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

Natural Product: NPC473094

Natural Product ID:	NPC473094
*Common Name:**	SSGAWPSGWGGBIW-SRYPRDQNSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	SSGAWPSGWGGBIW-SRYPRDQNSA-N
Standard InCHI:	InChI=1S/C23H22O11/c1-8-14-9(6-12(31-2)15(8)21(28)33-4)5-10-16(17(14)25)22(29)34-20(10)23(30)18(26)11(24)7-13(32-3)19(23)27/h5-7,18-20,25-27,30H,1-4H3/t18-,19+,20-,23-/m0/s1
SMILES:	CC1=C(C(=CC2=CC3=C(C(=C12)O)C(=O)OC3C4(C(C(=CC(=O)C4O)OC)O)O)OC)C(=O)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3609612
PubChem CID:	n.a.
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
NPO32655	actinomycete saccharothrix sp.	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[26317881]

☑ 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	22

Activity Type	# Activity
Cell Line	3
NON-MOLECULAR	1
Organism	21

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT111	Cell Line	K562	Homo sapiens	IC50	>	100000.0	nM	PMID[549765]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	>	100000.0	nM	PMID[549765]
NPT65	Cell Line	HepG2	Homo sapiens	IC50	>	100000.0	nM	PMID[549765]
NPT175	Organism	Enterococcus faecalis	Enterococcus faecalis	MIC	>	64.0	ug.mL-1	PMID[549765]
NPT1204	Organism	Enterococcus faecalis ATCC 29212	Enterococcus faecalis ATCC 29212	MIC	>	64.0	ug.mL-1	PMID[549765]
NPT17	Organism	Staphylococcus epidermidis	Staphylococcus epidermidis	MIC	>	64.0	ug.mL-1	PMID[549765]
NPT1277	Organism	Staphylococcus epidermidis ATCC 12228	Staphylococcus epidermidis ATCC 12228	MIC	>	64.0	ug.mL-1	PMID[549765]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	>	64.0	ug.mL-1	PMID[549765]
NPT173	Organism	Klebsiella pneumoniae	Klebsiella pneumoniae	MIC	>	64.0	ug.mL-1	PMID[549765]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	>	64.0	ug.mL-1	PMID[549765]
NPT1531	Organism	Enterococcus faecium	Enterococcus faecium	MIC	>	64.0	ug.mL-1	PMID[549765]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	MIC	>	64.0	ug.mL-1	PMID[549765]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	MIC	>	64.0	ug.mL-1	PMID[549765]
NPT3495	Organism	Morganella morganii	Morganella morganii	MIC	>	64.0	ug.mL-1	PMID[549765]
NPT766	Organism	Proteus vulgaris	Proteus vulgaris	MIC	>	64.0	ug.mL-1	PMID[549765]
NPT3163	Organism	Acinetobacter calcoaceticus	Acinetobacter calcoaceticus	MIC	>	64.0	ug.mL-1	PMID[549765]

☑ 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 NPC473094 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	360
0.1-0.2	1423
0.2-0.3	3089
0.3-0.4	6888
0.4-0.5	10401
0.5-0.6	5290
0.6-0.7	5494
0.7-0.8	7318
0.8-0.85	2126
0.85-0.9	296
0.9-0.95	9
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9937	High Similarity	NPC473096
0.9937	High Similarity	NPC473095
0.9434	High Similarity	NPC117985
0.9329	High Similarity	NPC473113
0.913	High Similarity	NPC472055
0.9068	High Similarity	NPC470339
0.9048	High Similarity	NPC324220
0.9048	High Similarity	NPC312630
0.9018	High Similarity	NPC478229
0.9012	High Similarity	NPC470810
0.9006	High Similarity	NPC246466
0.9	High Similarity	NPC208069
0.9	High Similarity	NPC471456
0.8994	High Similarity	NPC477683
0.8994	High Similarity	NPC477682
0.897	High Similarity	NPC20237
0.8963	High Similarity	NPC249181
0.8957	High Similarity	NPC478222
0.8947	High Similarity	NPC475656
0.8947	High Similarity	NPC475148
0.8944	High Similarity	NPC478223
0.8916	High Similarity	NPC283041
0.8909	High Similarity	NPC472049
0.8909	High Similarity	NPC191930
0.8908	High Similarity	NPC314672
0.8882	High Similarity	NPC68727
0.8868	High Similarity	NPC179178
0.8868	High Similarity	NPC119929
0.8841	High Similarity	NPC478134
0.8841	High Similarity	NPC269117
0.8827	High Similarity	NPC472050
0.882	High Similarity	NPC312482
0.882	High Similarity	NPC478231
0.882	High Similarity	NPC137301
0.8817	High Similarity	NPC98776
0.8812	High Similarity	NPC200773
0.8812	High Similarity	NPC240768
0.881	High Similarity	NPC17219
0.881	High Similarity	NPC313717
0.881	High Similarity	NPC315306
0.8788	High Similarity	NPC144843
0.878	High Similarity	NPC47623
0.878	High Similarity	NPC284495
0.8773	High Similarity	NPC472889
0.8772	High Similarity	NPC470334
0.8765	High Similarity	NPC69043
0.8765	High Similarity	NPC478230
0.8765	High Similarity	NPC470454
0.8765	High Similarity	NPC199533
0.8758	High Similarity	NPC470338
0.8758	High Similarity	NPC478224
0.8758	High Similarity	NPC470337
0.8758	High Similarity	NPC470340
0.8758	High Similarity	NPC175978
0.8758	High Similarity	NPC51824
0.8758	High Similarity	NPC167903
0.8758	High Similarity	NPC268992
0.8758	High Similarity	NPC113608
0.8758	High Similarity	NPC478220
0.8758	High Similarity	NPC115249
0.875	High Similarity	NPC191653
0.875	High Similarity	NPC473202
0.8743	High Similarity	NPC170245
0.8743	High Similarity	NPC178173
0.8743	High Similarity	NPC178851
0.8742	High Similarity	NPC470359
0.8735	High Similarity	NPC197168
0.8728	High Similarity	NPC228209
0.8728	High Similarity	NPC182693
0.8713	High Similarity	NPC475233
0.8712	High Similarity	NPC474360
0.8712	High Similarity	NPC164427
0.8706	High Similarity	NPC472054
0.8706	High Similarity	NPC470335
0.8706	High Similarity	NPC470336
0.8706	High Similarity	NPC154986
0.8704	High Similarity	NPC155686
0.8704	High Similarity	NPC471695
0.8704	High Similarity	NPC301233
0.8704	High Similarity	NPC192189
0.8698	High Similarity	NPC241874
0.8698	High Similarity	NPC298778
0.8696	High Similarity	NPC215921
0.8696	High Similarity	NPC70016
0.869	High Similarity	NPC324522
0.869	High Similarity	NPC105414
0.869	High Similarity	NPC234497
0.869	High Similarity	NPC474024
0.869	High Similarity	NPC472058
0.869	High Similarity	NPC470341
0.8688	High Similarity	NPC270160
0.8688	High Similarity	NPC237440
0.8688	High Similarity	NPC4423
0.8688	High Similarity	NPC77325
0.8683	High Similarity	NPC472057
0.8683	High Similarity	NPC326520
0.8683	High Similarity	NPC25361
0.8683	High Similarity	NPC472051
0.8679	High Similarity	NPC8817
0.8679	High Similarity	NPC166583
0.8679	High Similarity	NPC53362
0.8675	High Similarity	NPC472059
0.8675	High Similarity	NPC211107
0.8675	High Similarity	NPC472402
0.8671	High Similarity	NPC315221
0.8667	High Similarity	NPC470358
0.8659	High Similarity	NPC143328
0.8659	High Similarity	NPC77679
0.8659	High Similarity	NPC263483
0.8659	High Similarity	NPC190020
0.8659	High Similarity	NPC473395
0.8659	High Similarity	NPC84935
0.8655	High Similarity	NPC232412
0.8655	High Similarity	NPC98667
0.8655	High Similarity	NPC86809
0.8655	High Similarity	NPC68381
0.8655	High Similarity	NPC294149
0.8652	High Similarity	NPC314020
0.865	High Similarity	NPC175192
0.865	High Similarity	NPC317585
0.865	High Similarity	NPC208173
0.865	High Similarity	NPC326910
0.865	High Similarity	NPC472890
0.865	High Similarity	NPC99381
0.865	High Similarity	NPC79998
0.865	High Similarity	NPC478221
0.865	High Similarity	NPC170189
0.8647	High Similarity	NPC158226
0.8647	High Similarity	NPC472620
0.8647	High Similarity	NPC121333
0.8647	High Similarity	NPC471181
0.8642	High Similarity	NPC273483
0.8642	High Similarity	NPC76041
0.8642	High Similarity	NPC184284
0.8642	High Similarity	NPC180944
0.8642	High Similarity	NPC253904
0.8642	High Similarity	NPC321363
0.8642	High Similarity	NPC217447
0.8639	High Similarity	NPC259905
0.8639	High Similarity	NPC99613
0.8639	High Similarity	NPC49487
0.8634	High Similarity	NPC472891
0.8631	High Similarity	NPC255787
0.8631	High Similarity	NPC472452
0.8631	High Similarity	NPC20216
0.8629	High Similarity	NPC197972
0.8623	High Similarity	NPC472053
0.8623	High Similarity	NPC474240
0.8623	High Similarity	NPC475985
0.8623	High Similarity	NPC270837
0.8623	High Similarity	NPC474350
0.8623	High Similarity	NPC477689
0.8623	High Similarity	NPC41301
0.8621	High Similarity	NPC313452
0.8621	High Similarity	NPC8927
0.8616	High Similarity	NPC470357
0.8614	High Similarity	NPC74854
0.8614	High Similarity	NPC45124
0.8614	High Similarity	NPC30655
0.8614	High Similarity	NPC92589
0.8614	High Similarity	NPC87431
0.8614	High Similarity	NPC66288
0.8614	High Similarity	NPC316457
0.8613	High Similarity	NPC113446
0.8613	High Similarity	NPC245059
0.8613	High Similarity	NPC84494
0.8606	High Similarity	NPC45846
0.8606	High Similarity	NPC85121
0.8605	High Similarity	NPC469345
0.8598	High Similarity	NPC478027
0.8598	High Similarity	NPC150227
0.8598	High Similarity	NPC146211
0.8596	High Similarity	NPC476311
0.8596	High Similarity	NPC229051
0.8589	High Similarity	NPC478218
0.8589	High Similarity	NPC477691
0.8588	High Similarity	NPC477573
0.8588	High Similarity	NPC477572
0.8588	High Similarity	NPC251144
0.8588	High Similarity	NPC241387
0.8588	High Similarity	NPC124470
0.8588	High Similarity	NPC313304
0.8588	High Similarity	NPC477571
0.8588	High Similarity	NPC109827
0.858	High Similarity	NPC174486
0.858	High Similarity	NPC132990
0.858	High Similarity	NPC150131
0.858	High Similarity	NPC158761
0.858	High Similarity	NPC117854
0.858	High Similarity	NPC471180
0.858	High Similarity	NPC477154
0.858	High Similarity	NPC474417
0.858	High Similarity	NPC232645
0.858	High Similarity	NPC470569
0.858	High Similarity	NPC46882
0.858	High Similarity	NPC149526
0.858	High Similarity	NPC72958
0.858	High Similarity	NPC6588
0.858	High Similarity	NPC205918
0.858	High Similarity	NPC225419

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 NPC473094 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	314
0.1-0.2	898
0.2-0.3	1714
0.3-0.4	2550
0.4-0.5	1941
0.5-0.6	1080
0.6-0.7	442
0.7-0.8	180
0.8-0.85	27
0.85-0.9	4
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8675	High Similarity	NPD6232	Discontinued
0.8631	High Similarity	NPD7473	Discontinued
0.858	High Similarity	NPD7879	Clinical (unspecified phase)
0.8553	High Similarity	NPD2533	Approved
0.8553	High Similarity	NPD2534	Approved
0.8553	High Similarity	NPD2532	Approved
0.8434	Intermediate Similarity	NPD7075	Discontinued
0.8352	Intermediate Similarity	NPD8150	Discontinued
0.8314	Intermediate Similarity	NPD5844	Phase 1
0.8303	Intermediate Similarity	NPD6801	Discontinued
0.8293	Intermediate Similarity	NPD4380	Phase 2
0.8284	Intermediate Similarity	NPD6959	Discontinued
0.8276	Intermediate Similarity	NPD6559	Discontinued
0.8258	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.8253	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8253	Intermediate Similarity	NPD7819	Suspended
0.8253	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8249	Intermediate Similarity	NPD8434	Phase 2
0.8204	Intermediate Similarity	NPD3817	Phase 2
0.8155	Intermediate Similarity	NPD3882	Suspended
0.815	Intermediate Similarity	NPD3818	Discontinued
0.814	Intermediate Similarity	NPD6166	Phase 2
0.814	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.814	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8125	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8118	Intermediate Similarity	NPD7435	Discontinued
0.8098	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8095	Intermediate Similarity	NPD5402	Approved
0.809	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.8084	Intermediate Similarity	NPD1934	Approved
0.8072	Intermediate Similarity	NPD6599	Discontinued
0.8054	Intermediate Similarity	NPD6778	Approved
0.8054	Intermediate Similarity	NPD6777	Approved
0.8054	Intermediate Similarity	NPD6779	Approved
0.8054	Intermediate Similarity	NPD6776	Approved
0.8054	Intermediate Similarity	NPD6781	Approved
0.8054	Intermediate Similarity	NPD6780	Approved
0.8054	Intermediate Similarity	NPD6782	Approved
0.8047	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8036	Intermediate Similarity	NPD2801	Approved
0.8012	Intermediate Similarity	NPD5494	Approved
0.8012	Intermediate Similarity	NPD3226	Approved
0.8	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7976	Intermediate Similarity	NPD37	Approved
0.7953	Intermediate Similarity	NPD6234	Discontinued
0.795	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7943	Intermediate Similarity	NPD3751	Discontinued
0.7941	Intermediate Similarity	NPD4967	Phase 2
0.7941	Intermediate Similarity	NPD4966	Approved
0.7941	Intermediate Similarity	NPD4965	Approved
0.7937	Intermediate Similarity	NPD2935	Discontinued
0.7927	Intermediate Similarity	NPD6799	Approved
0.7919	Intermediate Similarity	NPD5711	Approved
0.7919	Intermediate Similarity	NPD5710	Approved
0.791	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.791	Intermediate Similarity	NPD6797	Phase 2
0.7895	Intermediate Similarity	NPD3749	Approved
0.7895	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7877	Intermediate Similarity	NPD8313	Approved
0.7877	Intermediate Similarity	NPD8312	Approved
0.7865	Intermediate Similarity	NPD7874	Approved
0.7865	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7865	Intermediate Similarity	NPD7251	Discontinued
0.7853	Intermediate Similarity	NPD4628	Phase 3
0.7853	Intermediate Similarity	NPD7074	Phase 3
0.7831	Intermediate Similarity	NPD1512	Approved
0.7831	Intermediate Similarity	NPD7697	Approved
0.7831	Intermediate Similarity	NPD7696	Phase 3
0.7831	Intermediate Similarity	NPD7698	Approved
0.7824	Intermediate Similarity	NPD1465	Phase 2
0.7821	Intermediate Similarity	NPD7808	Phase 3
0.7816	Intermediate Similarity	NPD3787	Discontinued
0.7812	Intermediate Similarity	NPD8151	Discontinued
0.7811	Intermediate Similarity	NPD7411	Suspended
0.7805	Intermediate Similarity	NPD6190	Approved
0.7797	Intermediate Similarity	NPD7054	Approved
0.7789	Intermediate Similarity	NPD7870	Phase 2
0.7789	Intermediate Similarity	NPD7871	Phase 2
0.7784	Intermediate Similarity	NPD5403	Approved
0.7784	Intermediate Similarity	NPD6535	Approved
0.7784	Intermediate Similarity	NPD6534	Approved
0.7778	Intermediate Similarity	NPD2346	Discontinued
0.7778	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.776	Intermediate Similarity	NPD7701	Phase 2
0.7753	Intermediate Similarity	NPD7472	Approved
0.7746	Intermediate Similarity	NPD919	Approved
0.774	Intermediate Similarity	NPD7228	Approved
0.7727	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7711	Intermediate Similarity	NPD1511	Approved
0.7711	Intermediate Similarity	NPD7390	Discontinued
0.7683	Intermediate Similarity	NPD2800	Approved
0.7669	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7669	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7665	Intermediate Similarity	NPD5401	Approved
0.7665	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.766	Intermediate Similarity	NPD7699	Phase 2
0.766	Intermediate Similarity	NPD7700	Phase 2
0.7657	Intermediate Similarity	NPD1247	Approved
0.7654	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7654	Intermediate Similarity	NPD1510	Phase 2
0.7641	Intermediate Similarity	NPD7783	Phase 2
0.7641	Intermediate Similarity	NPD7801	Approved
0.7641	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.764	Intermediate Similarity	NPD1607	Approved
0.7636	Intermediate Similarity	NPD3750	Approved
0.763	Intermediate Similarity	NPD7768	Phase 2
0.7622	Intermediate Similarity	NPD1549	Phase 2
0.7604	Intermediate Similarity	NPD8319	Approved
0.7604	Intermediate Similarity	NPD8320	Phase 1
0.7592	Intermediate Similarity	NPD6823	Phase 2
0.7588	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7576	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7574	Intermediate Similarity	NPD920	Approved
0.7571	Intermediate Similarity	NPD3926	Phase 2
0.7571	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.756	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.756	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7557	Intermediate Similarity	NPD7199	Phase 2
0.7516	Intermediate Similarity	NPD1240	Approved
0.75	Intermediate Similarity	NPD5404	Approved
0.75	Intermediate Similarity	NPD2796	Approved
0.75	Intermediate Similarity	NPD5408	Approved
0.75	Intermediate Similarity	NPD5406	Approved
0.75	Intermediate Similarity	NPD5405	Approved
0.7475	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.7471	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.747	Intermediate Similarity	NPD1243	Approved
0.7456	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7439	Intermediate Similarity	NPD2799	Discontinued
0.7425	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7416	Intermediate Similarity	NPD7229	Phase 3
0.7407	Intermediate Similarity	NPD4060	Phase 1
0.7396	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD2438	Suspended
0.7394	Intermediate Similarity	NPD1551	Phase 2
0.7391	Intermediate Similarity	NPD3764	Approved
0.7391	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7384	Intermediate Similarity	NPD7458	Discontinued
0.7377	Intermediate Similarity	NPD7240	Approved
0.7377	Intermediate Similarity	NPD7685	Pre-registration
0.7362	Intermediate Similarity	NPD230	Phase 1
0.735	Intermediate Similarity	NPD7930	Approved
0.7349	Intermediate Similarity	NPD2344	Approved
0.7345	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7337	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD7033	Discontinued
0.7333	Intermediate Similarity	NPD3748	Approved
0.733	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7322	Intermediate Similarity	NPD5953	Discontinued
0.7321	Intermediate Similarity	NPD7003	Approved
0.7321	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD6651	Approved
0.7289	Intermediate Similarity	NPD6100	Approved
0.7289	Intermediate Similarity	NPD6099	Approved
0.7284	Intermediate Similarity	NPD2313	Discontinued
0.7263	Intermediate Similarity	NPD6213	Phase 3
0.7263	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.7263	Intermediate Similarity	NPD6212	Phase 3
0.7256	Intermediate Similarity	NPD6355	Discontinued
0.7253	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7243	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7235	Intermediate Similarity	NPD3300	Phase 2
0.7233	Intermediate Similarity	NPD1283	Approved
0.7229	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7216	Intermediate Similarity	NPD8455	Phase 2
0.7213	Intermediate Similarity	NPD7286	Phase 2
0.7209	Intermediate Similarity	NPD6273	Approved
0.7208	Intermediate Similarity	NPD7211	Clinical (unspecified phase)
0.7195	Intermediate Similarity	NPD943	Approved
0.7195	Intermediate Similarity	NPD2979	Phase 3
0.7192	Intermediate Similarity	NPD8404	Phase 2
0.7178	Intermediate Similarity	NPD6798	Discontinued
0.7178	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD2309	Approved
0.7166	Intermediate Similarity	NPD8407	Phase 2
0.7158	Intermediate Similarity	NPD7177	Discontinued
0.7152	Intermediate Similarity	NPD447	Suspended
0.7143	Intermediate Similarity	NPD2403	Approved
0.7143	Intermediate Similarity	NPD5762	Approved
0.7143	Intermediate Similarity	NPD1471	Phase 3
0.7143	Intermediate Similarity	NPD5763	Approved
0.7143	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7136	Intermediate Similarity	NPD7907	Approved
0.7134	Intermediate Similarity	NPD6233	Phase 2
0.7128	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7122	Intermediate Similarity	NPD4665	Approved
0.7122	Intermediate Similarity	NPD4111	Phase 1
0.7121	Intermediate Similarity	NPD7999	Approved
0.7119	Intermediate Similarity	NPD5761	Phase 2
0.7119	Intermediate Similarity	NPD5760	Phase 2
0.7117	Intermediate Similarity	NPD4625	Phase 3
0.7109	Intermediate Similarity	NPD8067	Phase 3
0.7097	Intermediate Similarity	NPD6764	Approved
0.7097	Intermediate Similarity	NPD6765	Approved
0.7097	Intermediate Similarity	NPD8368	Discontinued
0.7081	Intermediate Similarity	NPD1470	Approved
0.7077	Intermediate Similarity	NPD8285	Discontinued
0.7072	Intermediate Similarity	NPD8127	Discontinued
0.7065	Intermediate Similarity	NPD7799	Discontinued
0.7059	Intermediate Similarity	NPD5698	Clinical (unspecified phase)

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