NPASS Compound

Structure

CID78966 OpenBabel06191715412D 28 30 0 0 1 0 0 0 0 0999 V2000 3.5491 1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3090 2.5691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5491 0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 -1.6910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5491 -1.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 -1.6910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2812 2.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5491 2.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.6180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 -1.1910 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.4152 3.3090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.8171 1.8090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.5491 -0.1910 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.9511 1.3090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.8171 -0.1910 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.9511 0.3090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.6831 3.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5878 0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 0.3090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0850 -1.1910 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.1472 3.3090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.4152 4.3090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.4152 0.3090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 4.3090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5878 0.8090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 2.8090 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 9 2 0 0 0 0 2 10 2 0 0 0 0 4 5 1 0 0 0 0 4 11 1 0 0 0 0 5 14 1 0 0 0 0 6 13 1 0 0 0 0 6 20 1 0 0 0 0 7 21 2 0 0 0 0 8 12 1 0 0 0 0 8 22 1 0 0 0 0 9 12 1 0 0 0 0 9 18 1 0 0 0 0 10 19 1 0 0 0 0 11 7 1 6 0 0 0 11 16 1 0 0 0 0 12 23 1 1 0 0 0 13 15 1 0 0 0 0 13 27 1 1 0 0 0 14 20 1 6 0 0 0 14 24 1 0 0 0 0 15 10 1 6 0 0 0 15 17 1 0 0 0 0 16 17 1 0 0 0 0 16 20 1 6 0 0 0 17 28 1 1 0 0 0 18 25 2 0 0 0 0 18 27 1 0 0 0 0 19 26 2 0 0 0 0 19 28 1 0 0 0 0 20 3 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	394.16
Volume:	385.946
LogP:	-0.188
LogD:	0.48
LogS:	-1.473
# Rotatable Bonds:	6
TPSA:	130.36
# H-Bond Aceptor:	8
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.335
Synthetic Accessibility Score:	5.088
Fsp3:	0.65
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	3
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.431
MDCK Permeability:	3.0409972168854438e-05
Pgp-inhibitor:	0.077
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.906
20% Bioavailability (F20%):	0.869
30% Bioavailability (F30%):	0.991

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.101
Plasma Protein Binding (PPB):	44.69829559326172%
Volume Distribution (VD):	0.911
Pgp-substrate:	57.58484649658203%

ADMET: Metabolism

CYP1A2-inhibitor:	0.029
CYP1A2-substrate:	0.041
CYP2C19-inhibitor:	0.011
CYP2C19-substrate:	0.067
CYP2C9-inhibitor:	0.007
CYP2C9-substrate:	0.046
CYP2D6-inhibitor:	0.004
CYP2D6-substrate:	0.089
CYP3A4-inhibitor:	0.073
CYP3A4-substrate:	0.216

ADMET: Excretion

Clearance (CL):	3.641
Half-life (T1/2):	0.847

ADMET: Toxicity

hERG Blockers:	0.062
Human Hepatotoxicity (H-HT):	0.574
Drug-inuced Liver Injury (DILI):	0.888
AMES Toxicity:	0.04
Rat Oral Acute Toxicity:	0.844
Maximum Recommended Daily Dose:	0.97
Skin Sensitization:	0.929
Carcinogencity:	0.075
Eye Corrosion:	0.038
Eye Irritation:	0.146
Respiratory Toxicity:	0.945

Download Data

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

Natural Product: NPC78966

Natural Product ID:	NPC78966
*Common Name:**	Malacitanolide
IUPAC Name:	[(3aR,4S,5aR,6R,9S,9aS,9bR)-9-formyl-6-hydroxy-5a-methyl-3-methylidene-2-oxo-4,5,6,7,8,9,9a,9b-octahydro-3aH-benzo[g][1]benzofuran-4-yl] (3R)-3,4-dihydroxy-2-methylidenebutanoate
Synonyms:	Malacitanolide
Standard InCHIKey:	OZJAAHIGUMFSHY-MYBIUHGVSA-N
Standard InCHI:	InChI=1S/C20H26O8/c1-9(12(23)8-22)18(25)27-13-6-20(3)14(24)5-4-11(7-21)16(20)17-15(13)10(2)19(26)28-17/h7,11-17,22-24H,1-2,4-6,8H2,3H3/t11-,12+,13+,14-,15-,16-,17+,20+/m1/s1
SMILES:	C=C([C@H](CO)O)C(=O)O[C@H]1C[C@@]2(C)[C@@H](CC[C@H](C=O)[C@@H]2[C@@H]2[C@@H]1C(=C)C(=O)O2)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL464125
PubChem CID:	10739390
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones [CHEMONTID:0001543] Sesquiterpene lactones [CHEMONTID:0001772] Eudesmanolides, secoeudesmanolides, and derivatives

*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
NPO21525	Centaurea spinosa	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16180824]
NPO3204	Centaurea malacitana	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9358646]
NPO18759.1	Centaurea attica ssp. attica	Subspecies	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3204	Centaurea malacitana	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21525	Centaurea spinosa	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	5
MIC	2

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

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT168	Cell Line	P388	Mus musculus	IC50	=	0.12	ug.mL-1	PMID[531191]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	0.12	ug.mL-1	PMID[531191]
NPT139	Cell Line	HT-29	Homo sapiens	IC50	=	0.12	ug.mL-1	PMID[531191]
NPT170	Cell Line	SK-MEL-28	Homo sapiens	IC50	=	0.12	ug.mL-1	PMID[531191]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	5.0	ug.mL-1	PMID[531190]
NPT729	Organism	Micrococcus luteus	Micrococcus luteus	MIC	=	5.0	ug.mL-1	PMID[531190]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	0.12	ug.mL-1	PMID[531191]

☑ 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 NPC78966 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	232
0.1-0.2	1496
0.2-0.3	4713
0.3-0.4	7527
0.4-0.5	12763
0.5-0.6	7043
0.6-0.7	6492
0.7-0.8	2221
0.8-0.85	151
0.85-0.9	45
0.9-0.95	11
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC284732
0.9899	High Similarity	NPC37628
0.9412	High Similarity	NPC474243
0.93	High Similarity	NPC156681
0.9286	High Similarity	NPC476807
0.9286	High Similarity	NPC476806
0.9184	High Similarity	NPC474395
0.91	High Similarity	NPC308824
0.901	High Similarity	NPC164551
0.898	High Similarity	NPC259042
0.898	High Similarity	NPC157686
0.8922	High Similarity	NPC99510
0.8922	High Similarity	NPC72842
0.8922	High Similarity	NPC61442
0.8911	High Similarity	NPC242666
0.8911	High Similarity	NPC111292
0.8878	High Similarity	NPC225474
0.8878	High Similarity	NPC24861
0.8878	High Similarity	NPC148000
0.8878	High Similarity	NPC469596
0.88	High Similarity	NPC473963
0.8725	High Similarity	NPC475958
0.87	High Similarity	NPC93245
0.87	High Similarity	NPC284518
0.87	High Similarity	NPC473964
0.8654	High Similarity	NPC283850
0.8627	High Similarity	NPC47024
0.86	High Similarity	NPC90014
0.8585	High Similarity	NPC273155
0.8571	High Similarity	NPC475776
0.8558	High Similarity	NPC96217
0.8519	High Similarity	NPC157476
0.8515	High Similarity	NPC228766
0.8515	High Similarity	NPC165528
0.8491	Intermediate Similarity	NPC166993
0.8469	Intermediate Similarity	NPC116620
0.8469	Intermediate Similarity	NPC194642
0.8462	Intermediate Similarity	NPC275990
0.844	Intermediate Similarity	NPC269530
0.8431	Intermediate Similarity	NPC136781
0.8431	Intermediate Similarity	NPC474921
0.8426	Intermediate Similarity	NPC100908
0.8411	Intermediate Similarity	NPC112895
0.8411	Intermediate Similarity	NPC231278
0.8411	Intermediate Similarity	NPC218123
0.84	Intermediate Similarity	NPC147272
0.8396	Intermediate Similarity	NPC138908
0.8396	Intermediate Similarity	NPC200957
0.8396	Intermediate Similarity	NPC295366
0.8365	Intermediate Similarity	NPC46848
0.8365	Intermediate Similarity	NPC148279
0.8364	Intermediate Similarity	NPC477126
0.835	Intermediate Similarity	NPC216478
0.8349	Intermediate Similarity	NPC94650
0.8333	Intermediate Similarity	NPC256227
0.8317	Intermediate Similarity	NPC473434
0.8317	Intermediate Similarity	NPC471446
0.8317	Intermediate Similarity	NPC474841
0.8302	Intermediate Similarity	NPC301787
0.8286	Intermediate Similarity	NPC76866
0.8286	Intermediate Similarity	NPC88203
0.8286	Intermediate Similarity	NPC246736
0.8286	Intermediate Similarity	NPC286519
0.8286	Intermediate Similarity	NPC304832
0.8286	Intermediate Similarity	NPC148628
0.8286	Intermediate Similarity	NPC214946
0.8269	Intermediate Similarity	NPC470388
0.8269	Intermediate Similarity	NPC293890
0.8265	Intermediate Similarity	NPC181103
0.8265	Intermediate Similarity	NPC175293
0.8265	Intermediate Similarity	NPC305029
0.8257	Intermediate Similarity	NPC124053
0.8257	Intermediate Similarity	NPC85391
0.8241	Intermediate Similarity	NPC306265
0.8235	Intermediate Similarity	NPC56369
0.8224	Intermediate Similarity	NPC37600
0.8224	Intermediate Similarity	NPC222833
0.8208	Intermediate Similarity	NPC122811
0.8208	Intermediate Similarity	NPC277074
0.8208	Intermediate Similarity	NPC87927
0.8208	Intermediate Similarity	NPC159533
0.8208	Intermediate Similarity	NPC209298
0.82	Intermediate Similarity	NPC153853
0.8198	Intermediate Similarity	NPC478212
0.819	Intermediate Similarity	NPC39683
0.819	Intermediate Similarity	NPC52899
0.819	Intermediate Similarity	NPC236585
0.819	Intermediate Similarity	NPC67251
0.819	Intermediate Similarity	NPC289148
0.819	Intermediate Similarity	NPC163963
0.8182	Intermediate Similarity	NPC213320
0.8173	Intermediate Similarity	NPC474793
0.8173	Intermediate Similarity	NPC28864
0.8173	Intermediate Similarity	NPC38296
0.8173	Intermediate Similarity	NPC26270
0.8173	Intermediate Similarity	NPC471038
0.8173	Intermediate Similarity	NPC20479
0.8173	Intermediate Similarity	NPC89099
0.8173	Intermediate Similarity	NPC38471
0.8173	Intermediate Similarity	NPC162459
0.8173	Intermediate Similarity	NPC98837
0.8163	Intermediate Similarity	NPC185638
0.8163	Intermediate Similarity	NPC85698
0.8148	Intermediate Similarity	NPC187435
0.8148	Intermediate Similarity	NPC201908
0.8148	Intermediate Similarity	NPC67321
0.8148	Intermediate Similarity	NPC176949
0.8148	Intermediate Similarity	NPC471246
0.8142	Intermediate Similarity	NPC473968
0.8142	Intermediate Similarity	NPC469684
0.8142	Intermediate Similarity	NPC53396
0.8142	Intermediate Similarity	NPC470775
0.8142	Intermediate Similarity	NPC58662
0.8142	Intermediate Similarity	NPC176513
0.8142	Intermediate Similarity	NPC98249
0.8131	Intermediate Similarity	NPC296950
0.8131	Intermediate Similarity	NPC84928
0.8131	Intermediate Similarity	NPC146731
0.8125	Intermediate Similarity	NPC117712
0.812	Intermediate Similarity	NPC24651
0.8113	Intermediate Similarity	NPC295791
0.8113	Intermediate Similarity	NPC170615
0.8108	Intermediate Similarity	NPC476801
0.8108	Intermediate Similarity	NPC474927
0.8108	Intermediate Similarity	NPC473397
0.81	Intermediate Similarity	NPC253618
0.81	Intermediate Similarity	NPC77001
0.8095	Intermediate Similarity	NPC477655
0.8095	Intermediate Similarity	NPC293866
0.8095	Intermediate Similarity	NPC477656
0.8095	Intermediate Similarity	NPC267921
0.8095	Intermediate Similarity	NPC287676
0.8091	Intermediate Similarity	NPC5103
0.8091	Intermediate Similarity	NPC137104
0.8091	Intermediate Similarity	NPC255655
0.8091	Intermediate Similarity	NPC320383
0.8091	Intermediate Similarity	NPC478209
0.8091	Intermediate Similarity	NPC471093
0.8091	Intermediate Similarity	NPC474786
0.8077	Intermediate Similarity	NPC96839
0.8077	Intermediate Similarity	NPC10864
0.8077	Intermediate Similarity	NPC111348
0.8073	Intermediate Similarity	NPC471094
0.8073	Intermediate Similarity	NPC476802
0.8073	Intermediate Similarity	NPC473410
0.8073	Intermediate Similarity	NPC469984
0.8073	Intermediate Similarity	NPC63841
0.8073	Intermediate Similarity	NPC275539
0.8073	Intermediate Similarity	NPC189075
0.8073	Intermediate Similarity	NPC89171
0.807	Intermediate Similarity	NPC108581
0.807	Intermediate Similarity	NPC478205
0.807	Intermediate Similarity	NPC470776
0.807	Intermediate Similarity	NPC478206
0.807	Intermediate Similarity	NPC284707
0.8058	Intermediate Similarity	NPC470232
0.8056	Intermediate Similarity	NPC28791
0.8039	Intermediate Similarity	NPC199543
0.8037	Intermediate Similarity	NPC216114
0.8037	Intermediate Similarity	NPC139347
0.8037	Intermediate Similarity	NPC120321
0.8036	Intermediate Similarity	NPC132668
0.8036	Intermediate Similarity	NPC94509
0.8036	Intermediate Similarity	NPC56448
0.8036	Intermediate Similarity	NPC471252
0.8036	Intermediate Similarity	NPC25909
0.8019	Intermediate Similarity	NPC471790
0.8019	Intermediate Similarity	NPC253886
0.8019	Intermediate Similarity	NPC252614
0.8019	Intermediate Similarity	NPC121218
0.8018	Intermediate Similarity	NPC469655
0.8018	Intermediate Similarity	NPC474846
0.8018	Intermediate Similarity	NPC56025
0.8018	Intermediate Similarity	NPC29505
0.8018	Intermediate Similarity	NPC469656
0.8018	Intermediate Similarity	NPC471251
0.8	Intermediate Similarity	NPC124512
0.8	Intermediate Similarity	NPC154906
0.8	Intermediate Similarity	NPC159763
0.8	Intermediate Similarity	NPC78427
0.8	Intermediate Similarity	NPC42662
0.8	Intermediate Similarity	NPC469986
0.8	Intermediate Similarity	NPC16911
0.8	Intermediate Similarity	NPC50847
0.8	Intermediate Similarity	NPC131903
0.8	Intermediate Similarity	NPC278386
0.8	Intermediate Similarity	NPC102741
0.8	Intermediate Similarity	NPC469983
0.8	Intermediate Similarity	NPC274827
0.7982	Intermediate Similarity	NPC88833
0.7982	Intermediate Similarity	NPC110496
0.7982	Intermediate Similarity	NPC475809
0.7982	Intermediate Similarity	NPC134430
0.7982	Intermediate Similarity	NPC186054
0.7982	Intermediate Similarity	NPC112780
0.7982	Intermediate Similarity	NPC143609
0.7982	Intermediate Similarity	NPC470854
0.7982	Intermediate Similarity	NPC471474
0.7982	Intermediate Similarity	NPC97908
0.7982	Intermediate Similarity	NPC55296

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 NPC78966 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	226
0.1-0.2	1971
0.2-0.3	3759
0.3-0.4	2027
0.4-0.5	666
0.5-0.6	280
0.6-0.7	184
0.7-0.8	36
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
0.8	Intermediate Similarity	NPD4225	Approved
0.7909	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7561	Intermediate Similarity	NPD7319	Approved
0.7373	Intermediate Similarity	NPD7115	Discovery
0.7368	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD6319	Approved
0.7317	Intermediate Similarity	NPD7507	Approved
0.7304	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7281	Intermediate Similarity	NPD6686	Approved
0.7273	Intermediate Similarity	NPD7639	Approved
0.7273	Intermediate Similarity	NPD7640	Approved
0.7273	Intermediate Similarity	NPD6921	Approved
0.7182	Intermediate Similarity	NPD7638	Approved
0.7119	Intermediate Similarity	NPD8133	Approved
0.7083	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7064	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7043	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.7016	Intermediate Similarity	NPD8328	Phase 3
0.6992	Remote Similarity	NPD8515	Approved
0.6992	Remote Similarity	NPD8517	Approved
0.6992	Remote Similarity	NPD8516	Approved
0.6992	Remote Similarity	NPD8513	Phase 3
0.6975	Remote Similarity	NPD4632	Approved
0.696	Remote Similarity	NPD7492	Approved
0.6957	Remote Similarity	NPD6008	Approved
0.6949	Remote Similarity	NPD6650	Approved
0.6949	Remote Similarity	NPD6649	Approved
0.6944	Remote Similarity	NPD8034	Phase 2
0.6944	Remote Similarity	NPD8035	Phase 2
0.6923	Remote Similarity	NPD6373	Approved
0.6923	Remote Similarity	NPD6372	Approved
0.6911	Remote Similarity	NPD6054	Approved
0.6905	Remote Similarity	NPD6616	Approved
0.6897	Remote Similarity	NPD5697	Approved
0.6891	Remote Similarity	NPD8297	Approved
0.6881	Remote Similarity	NPD5778	Approved
0.6881	Remote Similarity	NPD5779	Approved
0.6864	Remote Similarity	NPD6371	Approved
0.6864	Remote Similarity	NPD4634	Approved
0.6855	Remote Similarity	NPD6016	Approved
0.6855	Remote Similarity	NPD6015	Approved
0.685	Remote Similarity	NPD7078	Approved
0.6842	Remote Similarity	NPD7632	Discontinued
0.6838	Remote Similarity	NPD6881	Approved
0.6838	Remote Similarity	NPD6899	Approved
0.681	Remote Similarity	NPD7128	Approved
0.681	Remote Similarity	NPD6402	Approved
0.681	Remote Similarity	NPD6675	Approved
0.681	Remote Similarity	NPD5739	Approved
0.68	Remote Similarity	NPD5988	Approved
0.68	Remote Similarity	NPD6370	Approved
0.6797	Remote Similarity	NPD7736	Approved
0.6789	Remote Similarity	NPD7983	Approved
0.678	Remote Similarity	NPD6013	Approved
0.678	Remote Similarity	NPD6014	Approved
0.678	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.678	Remote Similarity	NPD6012	Approved
0.6774	Remote Similarity	NPD6059	Approved
0.6754	Remote Similarity	NPD5344	Discontinued
0.6752	Remote Similarity	NPD5701	Approved
0.6752	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.675	Remote Similarity	NPD6882	Approved
0.6727	Remote Similarity	NPD6399	Phase 3
0.6723	Remote Similarity	NPD7290	Approved
0.6723	Remote Similarity	NPD6883	Approved
0.6723	Remote Similarity	NPD7102	Approved
0.6719	Remote Similarity	NPD8074	Phase 3
0.6719	Remote Similarity	NPD8293	Discontinued
0.6698	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6697	Remote Similarity	NPD6698	Approved
0.6697	Remote Similarity	NPD46	Approved
0.6696	Remote Similarity	NPD5211	Phase 2
0.6696	Remote Similarity	NPD4697	Phase 3
0.6695	Remote Similarity	NPD7320	Approved
0.6695	Remote Similarity	NPD6011	Approved
0.6667	Remote Similarity	NPD8130	Phase 1
0.6667	Remote Similarity	NPD6847	Approved
0.6667	Remote Similarity	NPD6009	Approved
0.6667	Remote Similarity	NPD6617	Approved
0.6667	Remote Similarity	NPD6869	Approved
0.6637	Remote Similarity	NPD7902	Approved
0.6636	Remote Similarity	NPD6411	Approved
0.6636	Remote Similarity	NPD7637	Suspended
0.6613	Remote Similarity	NPD7328	Approved
0.6613	Remote Similarity	NPD7327	Approved
0.6587	Remote Similarity	NPD5983	Phase 2
0.6581	Remote Similarity	NPD5141	Approved
0.6571	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.656	Remote Similarity	NPD7516	Approved
0.6542	Remote Similarity	NPD1694	Approved
0.6522	Remote Similarity	NPD4696	Approved
0.6522	Remote Similarity	NPD5286	Approved
0.6522	Remote Similarity	NPD5285	Approved
0.6518	Remote Similarity	NPD7748	Approved
0.6491	Remote Similarity	NPD4755	Approved
0.6486	Remote Similarity	NPD7515	Phase 2
0.6486	Remote Similarity	NPD6079	Approved
0.6484	Remote Similarity	NPD7604	Phase 2
0.6481	Remote Similarity	NPD3618	Phase 1
0.6475	Remote Similarity	NPD6053	Discontinued
0.6471	Remote Similarity	NPD6412	Phase 2
0.6466	Remote Similarity	NPD1700	Approved
0.6457	Remote Similarity	NPD8033	Approved
0.6457	Remote Similarity	NPD8380	Approved
0.6457	Remote Similarity	NPD8335	Approved
0.6457	Remote Similarity	NPD8379	Approved
0.6457	Remote Similarity	NPD8296	Approved
0.6457	Remote Similarity	NPD8378	Approved
0.6455	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6455	Remote Similarity	NPD6101	Approved
0.6455	Remote Similarity	NPD5328	Approved
0.6452	Remote Similarity	NPD6274	Approved
0.641	Remote Similarity	NPD5224	Approved
0.641	Remote Similarity	NPD5226	Approved
0.641	Remote Similarity	NPD4633	Approved
0.641	Remote Similarity	NPD5225	Approved
0.6404	Remote Similarity	NPD5222	Approved
0.6404	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6404	Remote Similarity	NPD5221	Approved
0.6396	Remote Similarity	NPD5785	Approved
0.6393	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6393	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6389	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6385	Remote Similarity	NPD6336	Discontinued
0.6379	Remote Similarity	NPD6648	Approved
0.6379	Remote Similarity	NPD4700	Approved
0.6378	Remote Similarity	NPD8294	Approved
0.6378	Remote Similarity	NPD8377	Approved
0.6372	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6372	Remote Similarity	NPD5282	Discontinued
0.6372	Remote Similarity	NPD7900	Approved
0.6356	Remote Similarity	NPD5175	Approved
0.6356	Remote Similarity	NPD5174	Approved
0.6348	Remote Similarity	NPD5173	Approved
0.6346	Remote Similarity	NPD6114	Approved
0.6346	Remote Similarity	NPD6697	Approved
0.6346	Remote Similarity	NPD6118	Approved
0.6346	Remote Similarity	NPD6115	Approved
0.6328	Remote Similarity	NPD7503	Approved
0.6328	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6325	Remote Similarity	NPD5223	Approved
0.6299	Remote Similarity	NPD7101	Approved
0.6299	Remote Similarity	NPD7100	Approved
0.6288	Remote Similarity	NPD6033	Approved
0.6281	Remote Similarity	NPD4730	Approved
0.6281	Remote Similarity	NPD4729	Approved
0.6273	Remote Similarity	NPD3573	Approved
0.627	Remote Similarity	NPD6317	Approved
0.6269	Remote Similarity	NPD7260	Phase 2
0.6262	Remote Similarity	NPD3667	Approved
0.625	Remote Similarity	NPD6116	Phase 1
0.625	Remote Similarity	NPD4767	Approved
0.625	Remote Similarity	NPD7838	Discovery
0.625	Remote Similarity	NPD4768	Approved
0.6222	Remote Similarity	NPD6845	Suspended
0.622	Remote Similarity	NPD6313	Approved
0.622	Remote Similarity	NPD6335	Approved
0.622	Remote Similarity	NPD6314	Approved
0.6214	Remote Similarity	NPD3703	Phase 2
0.6207	Remote Similarity	NPD6083	Phase 2
0.6207	Remote Similarity	NPD6084	Phase 2
0.619	Remote Similarity	NPD6868	Approved
0.6182	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6179	Remote Similarity	NPD5251	Approved
0.6179	Remote Similarity	NPD5249	Phase 3
0.6179	Remote Similarity	NPD5248	Approved
0.6179	Remote Similarity	NPD5250	Approved
0.6179	Remote Similarity	NPD5247	Approved
0.6167	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6161	Remote Similarity	NPD1695	Approved
0.6154	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD5696	Approved
0.6154	Remote Similarity	NPD6117	Approved
0.6148	Remote Similarity	NPD5128	Approved
0.6147	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6147	Remote Similarity	NPD4786	Approved
0.614	Remote Similarity	NPD4202	Approved
0.6126	Remote Similarity	NPD7524	Approved
0.6121	Remote Similarity	NPD7839	Suspended
0.6083	Remote Similarity	NPD4754	Approved
0.6077	Remote Similarity	NPD6908	Approved
0.6077	Remote Similarity	NPD6909	Approved
0.6055	Remote Similarity	NPD4788	Approved
0.6055	Remote Similarity	NPD6695	Phase 3
0.6043	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6036	Remote Similarity	NPD5330	Approved
0.6036	Remote Similarity	NPD7521	Approved
0.6036	Remote Similarity	NPD6684	Approved
0.6036	Remote Similarity	NPD6409	Approved
0.6036	Remote Similarity	NPD7146	Approved
0.6036	Remote Similarity	NPD7334	Approved
0.6036	Remote Similarity	NPD5786	Approved
0.6034	Remote Similarity	NPD5695	Phase 3
0.6034	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6015	Remote Similarity	NPD8451	Approved
0.6	Remote Similarity	NPD5215	Approved
0.6	Remote Similarity	NPD6333	Approved
0.6	Remote Similarity	NPD5217	Approved
0.6	Remote Similarity	NPD3666	Approved
0.6	Remote Similarity	NPD5216	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