NPASS Compound

Structure

NPC473113 OpenBabel07101719252D 35 38 0 0 1 0 0 0 0 0999 V2000 4.3301 2.5000 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 -1.7321 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 3.0000 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 4.3301 -0.5000 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 4.3301 1.5000 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 1.7321 -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 5.1962 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 3.4641 1.0000 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 2.5981 1.5000 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 -0.8660 -0.5000 0.0000 C 0 0 1 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 0.0000 1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5981 -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 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 9 1 0 0 0 0 2 32 1 0 0 0 0 3 33 1 0 0 0 0 4 34 1 0 0 0 0 5 35 1 0 0 0 0 6 10 2 0 0 0 0 6 11 1 0 0 0 0 7 10 1 0 0 0 0 7 13 2 0 0 0 0 8 12 1 0 0 0 0 8 14 2 0 0 0 0 9 15 1 0 0 0 0 9 16 2 0 0 0 0 10 15 1 0 0 0 0 11 17 2 0 0 0 0 11 19 1 0 0 0 0 12 21 1 0 0 0 0 12 25 2 0 0 0 0 13 16 1 0 0 0 0 13 32 1 0 0 0 0 14 23 1 0 0 0 0 14 33 1 0 0 0 0 15 18 2 0 0 0 0 16 22 1 0 0 0 0 17 18 1 0 0 0 0 17 20 1 0 0 0 0 18 26 1 0 0 0 0 19 24 1 0 0 0 0 19 27 2 0 0 0 0 20 23 1 0 0 0 0 20 28 2 0 0 0 0 21 24 1 1 0 0 0 21 34 1 0 0 0 0 22 29 2 0 0 0 0 22 35 1 0 0 0 0 23 24 1 1 0 0 0 23 30 1 0 0 0 0 24 31 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	486.12
Volume:	459.762
LogP:	2.316
LogD:	1.734
LogS:	-3.92
# Rotatable Bonds:	5
TPSA:	165.89
# H-Bond Aceptor:	11
# H-Bond Donor:	3
# Rings:	4
# Heavy Atoms:	11

MedChem Properties

QED Drug-Likeness Score:	0.519
Synthetic Accessibility Score:	4.385
Fsp3:	0.333
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.491
MDCK Permeability:	1.6696309103281237e-05
Pgp-inhibitor:	0.136
Pgp-substrate:	0.784
Human Intestinal Absorption (HIA):	0.531
20% Bioavailability (F20%):	0.029
30% Bioavailability (F30%):	0.969

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.113
Plasma Protein Binding (PPB):	76.5403823852539%
Volume Distribution (VD):	1.036
Pgp-substrate:	18.794050216674805%

ADMET: Metabolism

CYP1A2-inhibitor:	0.486
CYP1A2-substrate:	0.989
CYP2C19-inhibitor:	0.027
CYP2C19-substrate:	0.787
CYP2C9-inhibitor:	0.047
CYP2C9-substrate:	0.051
CYP2D6-inhibitor:	0.003
CYP2D6-substrate:	0.112
CYP3A4-inhibitor:	0.285
CYP3A4-substrate:	0.809

ADMET: Excretion

Clearance (CL):	3.401
Half-life (T1/2):	0.067

ADMET: Toxicity

hERG Blockers:	0.004
Human Hepatotoxicity (H-HT):	0.426
Drug-inuced Liver Injury (DILI):	0.944
AMES Toxicity:	0.504
Rat Oral Acute Toxicity:	0.013
Maximum Recommended Daily Dose:	0.079
Skin Sensitization:	0.466
Carcinogencity:	0.077
Eye Corrosion:	0.003
Eye Irritation:	0.024
Respiratory Toxicity:	0.894

Download Data

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

Natural Product: NPC473113

Natural Product ID:	NPC473113
*Common Name:**	GGJYJLRNKHMHQJ-XWGVYQGASA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	GGJYJLRNKHMHQJ-XWGVYQGASA-N
Standard InCHI:	InChI=1S/C24H22O11/c1-9-15-10(7-13(32-2)16(9)22(29)35-5)6-11-17(18(15)26)20(28)23(30)14(33-3)8-12(25)21(34-4)24(23,31)19(11)27/h6-8,21,26,30-31H,1-5H3/t21-,23-,24-/m0/s1
SMILES:	COC1=CC(=O)[C@@H]([C@@]2([C@@]1(O)C(=O)c1c(O)c3c(cc1C2=O)cc(c(c3C)C(=O)OC)OC)O)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3609770
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000022] Naphthacenes [CHEMONTID:0000155] Tetracenequinones

*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	=	20800.0	nM	PMID[511257]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	16200.0	nM	PMID[511257]
NPT65	Cell Line	HepG2	Homo sapiens	IC50	=	7500.0	nM	PMID[511257]
NPT1204	Organism	Enterococcus faecalis ATCC 29212	Enterococcus faecalis ATCC 29212	MIC	>	64.0	ug.mL-1	PMID[511257]
NPT17	Organism	Staphylococcus epidermidis	Staphylococcus epidermidis	MIC	>	64.0	ug.mL-1	PMID[511257]
NPT1277	Organism	Staphylococcus epidermidis ATCC 12228	Staphylococcus epidermidis ATCC 12228	MIC	>	64.0	ug.mL-1	PMID[511257]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	>	64.0	ug.mL-1	PMID[511257]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	>	64.0	ug.mL-1	PMID[511257]
NPT1531	Organism	Enterococcus faecium	Enterococcus faecium	MIC	>	64.0	ug.mL-1	PMID[511257]
NPT175	Organism	Enterococcus faecalis	Enterococcus faecalis	MIC	>	64.0	ug.mL-1	PMID[511257]
NPT173	Organism	Klebsiella pneumoniae	Klebsiella pneumoniae	MIC	>	64.0	ug.mL-1	PMID[511257]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	MIC	>	64.0	ug.mL-1	PMID[511257]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	MIC	>	64.0	ug.mL-1	PMID[511257]
NPT3495	Organism	Morganella morganii	Morganella morganii	MIC	>	64.0	ug.mL-1	PMID[511257]
NPT766	Organism	Proteus vulgaris	Proteus vulgaris	MIC	>	64.0	ug.mL-1	PMID[511257]
NPT3163	Organism	Acinetobacter calcoaceticus	Acinetobacter calcoaceticus	MIC	>	64.0	ug.mL-1	PMID[511257]

☑ 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 NPC473113 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	393
0.1-0.2	1619
0.2-0.3	3513
0.3-0.4	8027
0.4-0.5	9902
0.5-0.6	4585
0.6-0.7	5864
0.7-0.8	7147
0.8-0.85	1503
0.85-0.9	140
0.9-0.95	3
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.939	High Similarity	NPC473095
0.939	High Similarity	NPC473096
0.9329	High Similarity	NPC473094
0.908	High Similarity	NPC314672
0.9064	High Similarity	NPC208069
0.8994	High Similarity	NPC472054
0.8976	High Similarity	NPC472049
0.8963	High Similarity	NPC284495
0.8953	High Similarity	NPC315221
0.8947	High Similarity	NPC477682
0.8947	High Similarity	NPC477683
0.8902	High Similarity	NPC182693
0.8902	High Similarity	NPC313452
0.8896	High Similarity	NPC474360
0.8869	High Similarity	NPC234497
0.8869	High Similarity	NPC470341
0.8869	High Similarity	NPC472058
0.8869	High Similarity	NPC324522
0.8869	High Similarity	NPC105414
0.8848	High Similarity	NPC472055
0.8841	High Similarity	NPC474637
0.8841	High Similarity	NPC263483
0.8837	High Similarity	NPC470334
0.883	High Similarity	NPC245975
0.8795	High Similarity	NPC117985
0.8795	High Similarity	NPC478134
0.8788	High Similarity	NPC470339
0.878	High Similarity	NPC472050
0.8773	High Similarity	NPC312482
0.8772	High Similarity	NPC470336
0.8772	High Similarity	NPC154986
0.8772	High Similarity	NPC470335
0.8757	High Similarity	NPC107009
0.8757	High Similarity	NPC295436
0.875	High Similarity	NPC472057
0.875	High Similarity	NPC26386
0.875	High Similarity	NPC472051
0.8728	High Similarity	NPC207467
0.8727	High Similarity	NPC246466
0.8721	High Similarity	NPC68381
0.872	High Similarity	NPC471456
0.872	High Similarity	NPC68727
0.8713	High Similarity	NPC158226
0.8713	High Similarity	NPC477836
0.8713	High Similarity	NPC294501
0.8706	High Similarity	NPC99613
0.8706	High Similarity	NPC49487
0.8704	High Similarity	NPC470568
0.8698	High Similarity	NPC477835
0.8698	High Similarity	NPC20237
0.869	High Similarity	NPC249181
0.8686	High Similarity	NPC475148
0.8686	High Similarity	NPC475656
0.8683	High Similarity	NPC478222
0.8678	High Similarity	NPC473785
0.8675	High Similarity	NPC324736
0.8667	High Similarity	NPC478223
0.8667	High Similarity	NPC474861
0.8663	High Similarity	NPC476311
0.8659	High Similarity	NPC192189
0.8659	High Similarity	NPC155686
0.8655	High Similarity	NPC478021
0.865	High Similarity	NPC470569
0.8647	High Similarity	NPC76647
0.8647	High Similarity	NPC283041
0.8639	High Similarity	NPC191930
0.8631	High Similarity	NPC478229
0.8631	High Similarity	NPC472059
0.8629	High Similarity	NPC475996
0.8623	High Similarity	NPC84571
0.8623	High Similarity	NPC470810
0.8623	High Similarity	NPC243701
0.8614	High Similarity	NPC199463
0.8614	High Similarity	NPC67197
0.8614	High Similarity	NPC201127
0.8614	High Similarity	NPC37543
0.8614	High Similarity	NPC472889
0.8613	High Similarity	NPC232412
0.8613	High Similarity	NPC162248
0.8613	High Similarity	NPC86809
0.8613	High Similarity	NPC474345
0.8613	High Similarity	NPC98667
0.8613	High Similarity	NPC477991
0.8613	High Similarity	NPC477992
0.8606	High Similarity	NPC226656
0.8606	High Similarity	NPC478221
0.8606	High Similarity	NPC66508
0.8606	High Similarity	NPC66029
0.8605	High Similarity	NPC111536
0.8605	High Similarity	NPC5029
0.8605	High Similarity	NPC271385
0.8605	High Similarity	NPC76128
0.8605	High Similarity	NPC30432
0.8598	High Similarity	NPC51824
0.8598	High Similarity	NPC113608
0.8598	High Similarity	NPC470337
0.8598	High Similarity	NPC470338
0.8598	High Similarity	NPC180944
0.8598	High Similarity	NPC470340
0.8598	High Similarity	NPC268992
0.8596	High Similarity	NPC205721
0.8596	High Similarity	NPC165979
0.8596	High Similarity	NPC163130
0.8589	High Similarity	NPC147735
0.8589	High Similarity	NPC294646
0.8588	High Similarity	NPC29160
0.8588	High Similarity	NPC197972
0.858	High Similarity	NPC101769
0.858	High Similarity	NPC472053
0.858	High Similarity	NPC112816
0.858	High Similarity	NPC172329
0.858	High Similarity	NPC470479
0.858	High Similarity	NPC2569
0.8571	High Similarity	NPC316457
0.8571	High Similarity	NPC219686
0.8571	High Similarity	NPC311740
0.8571	High Similarity	NPC318081
0.8571	High Similarity	NPC136878
0.8564	High Similarity	NPC470193
0.8564	High Similarity	NPC470198
0.8564	High Similarity	NPC470194
0.8564	High Similarity	NPC470195
0.8564	High Similarity	NPC470197
0.8564	High Similarity	NPC470200
0.8564	High Similarity	NPC282474
0.8564	High Similarity	NPC316274
0.8564	High Similarity	NPC470196
0.8563	High Similarity	NPC324220
0.8563	High Similarity	NPC104876
0.8563	High Similarity	NPC45846
0.8563	High Similarity	NPC245891
0.8563	High Similarity	NPC475233
0.8563	High Similarity	NPC477410
0.8563	High Similarity	NPC469345
0.8563	High Similarity	NPC312630
0.8563	High Similarity	NPC228654
0.8555	High Similarity	NPC470333
0.8555	High Similarity	NPC98776
0.8555	High Similarity	NPC131862
0.8555	High Similarity	NPC229051
0.8554	High Similarity	NPC478027
0.8554	High Similarity	NPC5379
0.8554	High Similarity	NPC14561
0.8554	High Similarity	NPC77807
0.8547	High Similarity	NPC313717
0.8547	High Similarity	NPC124470
0.8547	High Similarity	NPC109827
0.8547	High Similarity	NPC298778
0.8547	High Similarity	NPC315306
0.8547	High Similarity	NPC313304
0.8545	High Similarity	NPC470408
0.8545	High Similarity	NPC208806
0.8545	High Similarity	NPC474824
0.8545	High Similarity	NPC107109
0.8545	High Similarity	NPC137301
0.8545	High Similarity	NPC478231
0.8545	High Similarity	NPC472211
0.8545	High Similarity	NPC182921
0.8545	High Similarity	NPC218870
0.8539	High Similarity	NPC174486
0.8538	High Similarity	NPC234331
0.8537	High Similarity	NPC46882
0.8537	High Similarity	NPC132990
0.8537	High Similarity	NPC230848
0.8529	High Similarity	NPC471788
0.8528	High Similarity	NPC80370
0.8528	High Similarity	NPC280753
0.8528	High Similarity	NPC44378
0.8525	High Similarity	NPC131405
0.8523	High Similarity	NPC475161
0.8523	High Similarity	NPC265795
0.8523	High Similarity	NPC477860
0.8519	High Similarity	NPC312929
0.8519	High Similarity	NPC118027
0.8519	High Similarity	NPC245584
0.8519	High Similarity	NPC190648
0.8519	High Similarity	NPC289042
0.8519	High Similarity	NPC34802
0.8519	High Similarity	NPC56433
0.8519	High Similarity	NPC126767
0.8514	High Similarity	NPC476210
0.8514	High Similarity	NPC476199
0.8512	High Similarity	NPC472060
0.8512	High Similarity	NPC472052
0.8512	High Similarity	NPC470342
0.8508	High Similarity	NPC314020
0.8506	High Similarity	NPC186800
0.8506	High Similarity	NPC199533
0.8506	High Similarity	NPC294149
0.8506	High Similarity	NPC470454
0.8506	High Similarity	NPC470667
0.8503	High Similarity	NPC178976
0.85	High Similarity	NPC48474
0.8497	Intermediate Similarity	NPC270027
0.8497	Intermediate Similarity	NPC472620
0.8497	Intermediate Similarity	NPC118128
0.8497	Intermediate Similarity	NPC91650
0.8494	Intermediate Similarity	NPC478133
0.8494	Intermediate Similarity	NPC472890
0.8494	Intermediate Similarity	NPC3898

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 NPC473113 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	349
0.1-0.2	984
0.2-0.3	1796
0.3-0.4	2588
0.4-0.5	1921
0.5-0.6	950
0.6-0.7	375
0.7-0.8	165
0.8-0.85	19
0.85-0.9	3
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.875	High Similarity	NPD7879	Clinical (unspecified phase)
0.8743	High Similarity	NPD6232	Discontinued
0.8698	High Similarity	NPD7473	Discontinued
0.8393	Intermediate Similarity	NPD7075	Discontinued
0.8324	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.8315	Intermediate Similarity	NPD8150	Discontinued
0.8303	Intermediate Similarity	NPD3226	Approved
0.828	Intermediate Similarity	NPD7435	Discontinued
0.8276	Intermediate Similarity	NPD5844	Phase 1
0.8246	Intermediate Similarity	NPD6959	Discontinued
0.8214	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8155	Intermediate Similarity	NPD6801	Discontinued
0.8144	Intermediate Similarity	NPD4380	Phase 2
0.8118	Intermediate Similarity	NPD6782	Approved
0.8118	Intermediate Similarity	NPD6780	Approved
0.8118	Intermediate Similarity	NPD6776	Approved
0.8118	Intermediate Similarity	NPD6777	Approved
0.8118	Intermediate Similarity	NPD6781	Approved
0.8118	Intermediate Similarity	NPD6778	Approved
0.8118	Intermediate Similarity	NPD6779	Approved
0.8118	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8114	Intermediate Similarity	NPD3751	Discontinued
0.8107	Intermediate Similarity	NPD7819	Suspended
0.8095	Intermediate Similarity	NPD7411	Suspended
0.8061	Intermediate Similarity	NPD2532	Approved
0.8061	Intermediate Similarity	NPD2534	Approved
0.8061	Intermediate Similarity	NPD2533	Approved
0.8059	Intermediate Similarity	NPD3817	Phase 2
0.8059	Intermediate Similarity	NPD5402	Approved
0.8036	Intermediate Similarity	NPD6599	Discontinued
0.8021	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.8021	Intermediate Similarity	NPD7874	Approved
0.8011	Intermediate Similarity	NPD8434	Phase 2
0.8	Intermediate Similarity	NPD6166	Phase 2
0.8	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7989	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7956	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7953	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7907	Intermediate Similarity	NPD3882	Suspended
0.7901	Intermediate Similarity	NPD2935	Discontinued
0.7895	Intermediate Similarity	NPD7698	Approved
0.7895	Intermediate Similarity	NPD7697	Approved
0.7895	Intermediate Similarity	NPD7696	Phase 3
0.7892	Intermediate Similarity	NPD6799	Approved
0.7877	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7876	Intermediate Similarity	NPD8151	Discontinued
0.7865	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7853	Intermediate Similarity	NPD7870	Phase 2
0.7853	Intermediate Similarity	NPD7871	Phase 2
0.7849	Intermediate Similarity	NPD6534	Approved
0.7849	Intermediate Similarity	NPD6535	Approved
0.7845	Intermediate Similarity	NPD8313	Approved
0.7845	Intermediate Similarity	NPD8312	Approved
0.7844	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.784	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7836	Intermediate Similarity	NPD1934	Approved
0.7833	Intermediate Similarity	NPD6559	Discontinued
0.7824	Intermediate Similarity	NPD7701	Phase 2
0.7791	Intermediate Similarity	NPD1465	Phase 2
0.7791	Intermediate Similarity	NPD2801	Approved
0.7784	Intermediate Similarity	NPD7390	Discontinued
0.7784	Intermediate Similarity	NPD3787	Discontinued
0.7778	Intermediate Similarity	NPD6797	Phase 2
0.7771	Intermediate Similarity	NPD5494	Approved
0.7771	Intermediate Similarity	NPD6190	Approved
0.776	Intermediate Similarity	NPD8319	Approved
0.776	Intermediate Similarity	NPD8320	Phase 1
0.7759	Intermediate Similarity	NPD3749	Approved
0.7759	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7758	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7751	Intermediate Similarity	NPD5403	Approved
0.7738	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7735	Intermediate Similarity	NPD7251	Discontinued
0.7725	Intermediate Similarity	NPD7700	Phase 2
0.7725	Intermediate Similarity	NPD7699	Phase 2
0.7709	Intermediate Similarity	NPD3818	Discontinued
0.7704	Intermediate Similarity	NPD7801	Approved
0.7701	Intermediate Similarity	NPD7768	Phase 2
0.7697	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD7808	Phase 3
0.7683	Intermediate Similarity	NPD5408	Approved
0.7683	Intermediate Similarity	NPD5406	Approved
0.7683	Intermediate Similarity	NPD5404	Approved
0.7683	Intermediate Similarity	NPD5405	Approved
0.7636	Intermediate Similarity	NPD2346	Discontinued
0.7633	Intermediate Similarity	NPD5401	Approved
0.7633	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.763	Intermediate Similarity	NPD37	Approved
0.7627	Intermediate Similarity	NPD1247	Approved
0.7624	Intermediate Similarity	NPD7074	Phase 3
0.7624	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.7622	Intermediate Similarity	NPD1510	Phase 2
0.7614	Intermediate Similarity	NPD6234	Discontinued
0.7607	Intermediate Similarity	NPD1607	Approved
0.7605	Intermediate Similarity	NPD3750	Approved
0.7605	Intermediate Similarity	NPD4628	Phase 3
0.7588	Intermediate Similarity	NPD1512	Approved
0.7569	Intermediate Similarity	NPD7054	Approved
0.7565	Intermediate Similarity	NPD6823	Phase 2
0.7558	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7558	Intermediate Similarity	NPD7458	Discontinued
0.7527	Intermediate Similarity	NPD7472	Approved
0.7525	Intermediate Similarity	NPD7783	Phase 2
0.7525	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7514	Intermediate Similarity	NPD919	Approved
0.75	Intermediate Similarity	NPD4965	Approved
0.75	Intermediate Similarity	NPD4967	Phase 2
0.75	Intermediate Similarity	NPD4966	Approved
0.75	Intermediate Similarity	NPD7003	Approved
0.7486	Intermediate Similarity	NPD5711	Approved
0.7486	Intermediate Similarity	NPD5710	Approved
0.7485	Intermediate Similarity	NPD1549	Phase 2
0.7485	Intermediate Similarity	NPD1240	Approved
0.7471	Intermediate Similarity	NPD1511	Approved
0.7425	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7425	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7418	Intermediate Similarity	NPD7228	Approved
0.7416	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7409	Intermediate Similarity	NPD8285	Discontinued
0.7396	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD2796	Approved
0.736	Intermediate Similarity	NPD7211	Clinical (unspecified phase)
0.7348	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7348	Intermediate Similarity	NPD3926	Phase 2
0.7341	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.733	Intermediate Similarity	NPD6213	Phase 3
0.733	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.733	Intermediate Similarity	NPD6212	Phase 3
0.7326	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7305	Intermediate Similarity	NPD2799	Discontinued
0.7305	Intermediate Similarity	NPD3748	Approved
0.7297	Intermediate Similarity	NPD5953	Discontinued
0.7294	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7294	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD4060	Phase 1
0.7267	Intermediate Similarity	NPD1470	Approved
0.7262	Intermediate Similarity	NPD1551	Phase 2
0.7241	Intermediate Similarity	NPD920	Approved
0.7235	Intermediate Similarity	NPD2800	Approved
0.7229	Intermediate Similarity	NPD230	Phase 1
0.7228	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7228	Intermediate Similarity	NPD7177	Discontinued
0.7219	Intermediate Similarity	NPD1471	Phase 3
0.7209	Intermediate Similarity	NPD3300	Phase 2
0.7202	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7194	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7186	Intermediate Similarity	NPD6651	Approved
0.7169	Intermediate Similarity	NPD943	Approved
0.7166	Intermediate Similarity	NPD7685	Pre-registration
0.716	Intermediate Similarity	NPD2438	Suspended
0.7152	Intermediate Similarity	NPD2313	Discontinued
0.7152	Intermediate Similarity	NPD3764	Approved
0.7152	Intermediate Similarity	NPD6798	Discontinued
0.7143	Intermediate Similarity	NPD7199	Phase 2
0.7135	Intermediate Similarity	NPD1243	Approved
0.7126	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7118	Intermediate Similarity	NPD2344	Approved
0.7108	Intermediate Similarity	NPD6233	Phase 2
0.7104	Intermediate Similarity	NPD7229	Phase 3
0.7099	Intermediate Similarity	NPD1283	Approved
0.7097	Intermediate Similarity	NPD7286	Phase 2
0.7095	Intermediate Similarity	NPD8455	Phase 2
0.7086	Intermediate Similarity	NPD6273	Approved
0.7074	Intermediate Similarity	NPD7240	Approved
0.7069	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD6100	Approved
0.7059	Intermediate Similarity	NPD6099	Approved
0.7033	Intermediate Similarity	NPD7907	Approved
0.7028	Intermediate Similarity	NPD8058	Clinical (unspecified phase)
0.7028	Intermediate Similarity	NPD8059	Phase 3
0.7027	Intermediate Similarity	NPD2403	Approved
0.7024	Intermediate Similarity	NPD6355	Discontinued
0.7024	Intermediate Similarity	NPD447	Suspended
0.7019	Intermediate Similarity	NPD1201	Approved
0.7011	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.6995	Remote Similarity	NPD8435	Approved
0.6995	Remote Similarity	NPD8360	Approved
0.6995	Remote Similarity	NPD8361	Approved
0.6994	Remote Similarity	NPD8166	Discontinued
0.6984	Remote Similarity	NPD8368	Discontinued
0.6964	Remote Similarity	NPD2979	Phase 3
0.6957	Remote Similarity	NPD8127	Discontinued
0.6954	Remote Similarity	NPD2309	Approved
0.6952	Remote Similarity	NPD7799	Discontinued
0.6946	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6946	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6946	Remote Similarity	NPD3268	Approved
0.6928	Remote Similarity	NPD6832	Phase 2
0.6923	Remote Similarity	NPD8404	Phase 2
0.6919	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD1281	Approved
0.6914	Remote Similarity	NPD7236	Approved
0.6911	Remote Similarity	NPD5035	Approved
0.691	Remote Similarity	NPD7239	Suspended
0.6909	Remote Similarity	NPD2798	Approved
0.6908	Remote Similarity	NPD7930	Approved
0.6907	Remote Similarity	NPD4287	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