NPASS Compound

Structure

CID224689 OpenBabel06191716022D 25 28 0 0 1 0 0 0 0 0999 V2000 3.3793 0.3900 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3517 -0.0001 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5652 -2.1989 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8138 -0.7396 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9173 1.2321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7034 -0.0002 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8126 -1.7483 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3700 -1.3683 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0276 0.3901 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -1.1680 -1.5494 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0098 -0.3670 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4205 -0.6955 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.9215 -0.9214 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2589 -0.3371 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.9260 -0.2366 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -0.9211 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.0276 1.1705 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8794 0.2949 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7980 0.4609 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.3518 1.5607 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4822 0.9445 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.2096 0.3755 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.7035 1.5606 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.7979 -0.4607 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 6 1 0 0 0 0 2 9 1 0 0 0 0 3 10 1 0 0 0 0 4 11 2 0 0 0 0 6 9 1 0 0 0 0 7 8 1 0 0 0 0 7 10 1 0 0 0 0 9 18 1 0 0 0 0 10 13 2 0 0 0 0 11 12 1 0 0 0 0 11 19 1 0 0 0 0 12 8 1 1 0 0 0 12 15 1 0 0 0 0 13 14 1 0 0 0 0 14 15 1 0 0 0 0 14 20 1 1 0 0 0 15 23 1 1 0 0 0 16 13 1 1 0 0 0 16 17 1 0 0 0 0 16 25 1 0 0 0 0 17 20 1 1 0 0 0 17 24 1 0 0 0 0 18 21 2 0 0 0 0 18 24 1 0 0 0 0 19 22 2 0 0 0 0 19 23 1 0 0 0 0 20 5 1 6 0 0 0 20 25 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	346.18
Volume:	353.656
LogP:	3.74
LogD:	3.118
LogS:	-3.96
# Rotatable Bonds:	4
TPSA:	61.83
# H-Bond Aceptor:	5
# H-Bond Donor:	0
# Rings:	5
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.447
Synthetic Accessibility Score:	5.547
Fsp3:	0.7
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	2
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.659
MDCK Permeability:	2.503657015040517e-05
Pgp-inhibitor:	0.006
Pgp-substrate:	0.011
Human Intestinal Absorption (HIA):	0.008
20% Bioavailability (F20%):	0.008
30% Bioavailability (F30%):	0.838

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.301
Plasma Protein Binding (PPB):	82.19734191894531%
Volume Distribution (VD):	2.053
Pgp-substrate:	12.872303009033203%

ADMET: Metabolism

CYP1A2-inhibitor:	0.69
CYP1A2-substrate:	0.222
CYP2C19-inhibitor:	0.338
CYP2C19-substrate:	0.347
CYP2C9-inhibitor:	0.372
CYP2C9-substrate:	0.03
CYP2D6-inhibitor:	0.041
CYP2D6-substrate:	0.067
CYP3A4-inhibitor:	0.819
CYP3A4-substrate:	0.245

ADMET: Excretion

Clearance (CL):	15.58
Half-life (T1/2):	0.027

ADMET: Toxicity

hERG Blockers:	0.031
Human Hepatotoxicity (H-HT):	0.83
Drug-inuced Liver Injury (DILI):	0.702
AMES Toxicity:	0.035
Rat Oral Acute Toxicity:	0.868
Maximum Recommended Daily Dose:	0.24
Skin Sensitization:	0.458
Carcinogencity:	0.123
Eye Corrosion:	0.905
Eye Irritation:	0.105
Respiratory Toxicity:	0.986

Download Data

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

Natural Product: NPC224689

Natural Product ID:	NPC224689
*Common Name:**	3Beta-O-(2-Methylbutyryl)Moroccolide A
IUPAC Name:	n.a.
Synonyms:	3beta-O-(2-methylbutyryl)moroccolide A
Standard InCHIKey:	FPLUWNGZVAMKNR-BTAUDAJJSA-N
Standard InCHI:	InChI=1S/C20H26O5/c1-6-9(2)18(21)24-17-16-13-10(3)7-8-12-11(4)19(22)23-15(12)14(13)20(17,5)25-16/h9,12,14-17H,4,6-8H2,1-3,5H3/t9?,12-,14-,15+,16+,17-,20-/m0/s1
SMILES:	CCC(C(=O)O[C@H]1[C@@H]2O[C@@]1(C)[C@H]1C2=C(C)CC[C@@H]2[C@H]1OC(=O)C2=C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL518210
PubChem CID:	9997743
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:0001771] Germacranolides 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
NPO17270	Warionia saharae	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11975493]
NPO17270	Warionia saharae	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO17270	Warionia saharae	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17270	Warionia saharae	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	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	IC50	=	1.0	ug.mL-1	PMID[506874]

☑ 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 NPC224689 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	297
0.1-0.2	1822
0.2-0.3	6729
0.3-0.4	15954
0.4-0.5	9839
0.5-0.6	5958
0.6-0.7	1793
0.7-0.8	286
0.8-0.85	15
0.85-0.9	0
0.9-0.95	3
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9355	High Similarity	NPC70865
0.9121	High Similarity	NPC472874
0.9062	High Similarity	NPC124881
0.8817	High Similarity	NPC127019
0.8764	High Similarity	NPC235792
0.8723	High Similarity	NPC213698
0.8723	High Similarity	NPC67584
0.8681	High Similarity	NPC224652
0.866	High Similarity	NPC150923
0.8632	High Similarity	NPC213078
0.8542	High Similarity	NPC181151
0.8542	High Similarity	NPC161493
0.8526	High Similarity	NPC52044
0.8526	High Similarity	NPC170120
0.8298	Intermediate Similarity	NPC301969
0.8298	Intermediate Similarity	NPC37607
0.8265	Intermediate Similarity	NPC221615
0.8261	Intermediate Similarity	NPC107787
0.8261	Intermediate Similarity	NPC67493
0.8261	Intermediate Similarity	NPC64153
0.8229	Intermediate Similarity	NPC198853
0.8229	Intermediate Similarity	NPC470010
0.8229	Intermediate Similarity	NPC262133
0.8229	Intermediate Similarity	NPC323008
0.8229	Intermediate Similarity	NPC470013
0.8229	Intermediate Similarity	NPC477131
0.8222	Intermediate Similarity	NPC246076
0.8211	Intermediate Similarity	NPC133698
0.82	Intermediate Similarity	NPC86077
0.8191	Intermediate Similarity	NPC472872
0.8191	Intermediate Similarity	NPC4986
0.8172	Intermediate Similarity	NPC231889
0.8172	Intermediate Similarity	NPC24728
0.8163	Intermediate Similarity	NPC471150
0.8152	Intermediate Similarity	NPC78089
0.8144	Intermediate Similarity	NPC472873
0.8125	Intermediate Similarity	NPC81419
0.8125	Intermediate Similarity	NPC179746
0.8111	Intermediate Similarity	NPC281949
0.8111	Intermediate Similarity	NPC301477
0.8111	Intermediate Similarity	NPC25684
0.8105	Intermediate Similarity	NPC475748
0.8085	Intermediate Similarity	NPC471149
0.8085	Intermediate Similarity	NPC79549
0.8065	Intermediate Similarity	NPC304558
0.8065	Intermediate Similarity	NPC50637
0.8058	Intermediate Similarity	NPC26617
0.8043	Intermediate Similarity	NPC115786
0.8043	Intermediate Similarity	NPC156485
0.8041	Intermediate Similarity	NPC473330
0.8041	Intermediate Similarity	NPC473316
0.8039	Intermediate Similarity	NPC100487
0.8021	Intermediate Similarity	NPC131209
0.8021	Intermediate Similarity	NPC208886
0.8021	Intermediate Similarity	NPC12172
0.8	Intermediate Similarity	NPC283409
0.8	Intermediate Similarity	NPC151770
0.8	Intermediate Similarity	NPC186861
0.8	Intermediate Similarity	NPC215556
0.7961	Intermediate Similarity	NPC54737
0.7961	Intermediate Similarity	NPC243998
0.7961	Intermediate Similarity	NPC223450
0.7959	Intermediate Similarity	NPC304886
0.7938	Intermediate Similarity	NPC476300
0.7938	Intermediate Similarity	NPC475912
0.7938	Intermediate Similarity	NPC135776
0.7935	Intermediate Similarity	NPC170286
0.7935	Intermediate Similarity	NPC318468
0.7917	Intermediate Similarity	NPC297474
0.7917	Intermediate Similarity	NPC216284
0.7917	Intermediate Similarity	NPC54065
0.7917	Intermediate Similarity	NPC51004
0.7912	Intermediate Similarity	NPC141810
0.79	Intermediate Similarity	NPC45125
0.79	Intermediate Similarity	NPC187268
0.7895	Intermediate Similarity	NPC207114
0.7895	Intermediate Similarity	NPC217983
0.7895	Intermediate Similarity	NPC91248
0.7889	Intermediate Similarity	NPC182550
0.7879	Intermediate Similarity	NPC24956
0.7879	Intermediate Similarity	NPC18019
0.7865	Intermediate Similarity	NPC470240
0.7865	Intermediate Similarity	NPC476794
0.7857	Intermediate Similarity	NPC474338
0.7835	Intermediate Similarity	NPC475925
0.7835	Intermediate Similarity	NPC171360
0.7835	Intermediate Similarity	NPC63193
0.7835	Intermediate Similarity	NPC133888
0.7835	Intermediate Similarity	NPC57304
0.7835	Intermediate Similarity	NPC191339
0.7835	Intermediate Similarity	NPC286341
0.7835	Intermediate Similarity	NPC184063
0.7835	Intermediate Similarity	NPC293001
0.7835	Intermediate Similarity	NPC29821
0.7835	Intermediate Similarity	NPC30515
0.7835	Intermediate Similarity	NPC35959
0.7835	Intermediate Similarity	NPC155215
0.7835	Intermediate Similarity	NPC184463
0.7822	Intermediate Similarity	NPC471381
0.7812	Intermediate Similarity	NPC166919
0.7812	Intermediate Similarity	NPC155935
0.7812	Intermediate Similarity	NPC473564
0.7812	Intermediate Similarity	NPC307411
0.78	Intermediate Similarity	NPC474313
0.78	Intermediate Similarity	NPC311904
0.7789	Intermediate Similarity	NPC186148
0.7789	Intermediate Similarity	NPC270270
0.7789	Intermediate Similarity	NPC475703
0.7789	Intermediate Similarity	NPC190753
0.7778	Intermediate Similarity	NPC167893
0.7778	Intermediate Similarity	NPC36954
0.7778	Intermediate Similarity	NPC270013
0.7778	Intermediate Similarity	NPC476053
0.7778	Intermediate Similarity	NPC14961
0.7778	Intermediate Similarity	NPC163228
0.7766	Intermediate Similarity	NPC204105
0.7766	Intermediate Similarity	NPC300082
0.7766	Intermediate Similarity	NPC215364
0.7766	Intermediate Similarity	NPC284534
0.7755	Intermediate Similarity	NPC258216
0.7755	Intermediate Similarity	NPC212486
0.7742	Intermediate Similarity	NPC272814
0.7736	Intermediate Similarity	NPC139838
0.7736	Intermediate Similarity	NPC59489
0.7732	Intermediate Similarity	NPC312042
0.7732	Intermediate Similarity	NPC19087
0.7732	Intermediate Similarity	NPC474323
0.7732	Intermediate Similarity	NPC35809
0.7732	Intermediate Similarity	NPC80875
0.7732	Intermediate Similarity	NPC206614
0.7732	Intermediate Similarity	NPC62815
0.7723	Intermediate Similarity	NPC279561
0.7723	Intermediate Similarity	NPC208233
0.7717	Intermediate Similarity	NPC39411
0.7717	Intermediate Similarity	NPC255580
0.7708	Intermediate Similarity	NPC58219
0.7708	Intermediate Similarity	NPC202672
0.7708	Intermediate Similarity	NPC177629
0.77	Intermediate Similarity	NPC476315
0.77	Intermediate Similarity	NPC279621
0.7692	Intermediate Similarity	NPC617
0.7684	Intermediate Similarity	NPC284902
0.7684	Intermediate Similarity	NPC187661
0.7684	Intermediate Similarity	NPC162071
0.7677	Intermediate Similarity	NPC471147
0.7677	Intermediate Similarity	NPC140543
0.7677	Intermediate Similarity	NPC474035
0.7677	Intermediate Similarity	NPC81386
0.7677	Intermediate Similarity	NPC476267
0.7667	Intermediate Similarity	NPC65603
0.7653	Intermediate Similarity	NPC221282
0.7642	Intermediate Similarity	NPC117604
0.7634	Intermediate Similarity	NPC89555
0.7629	Intermediate Similarity	NPC32922
0.7629	Intermediate Similarity	NPC92974
0.7629	Intermediate Similarity	NPC38392
0.7624	Intermediate Similarity	NPC108475
0.7624	Intermediate Similarity	NPC170143
0.7624	Intermediate Similarity	NPC213947
0.7624	Intermediate Similarity	NPC471140
0.7619	Intermediate Similarity	NPC44004
0.7609	Intermediate Similarity	NPC69271
0.7609	Intermediate Similarity	NPC74673
0.7609	Intermediate Similarity	NPC474981
0.7609	Intermediate Similarity	NPC276356
0.7609	Intermediate Similarity	NPC302426
0.7604	Intermediate Similarity	NPC5130
0.7604	Intermediate Similarity	NPC160138
0.7604	Intermediate Similarity	NPC118601
0.76	Intermediate Similarity	NPC475659
0.7596	Intermediate Similarity	NPC475871
0.7596	Intermediate Similarity	NPC475945
0.7593	Intermediate Similarity	NPC474750
0.7579	Intermediate Similarity	NPC165162
0.7579	Intermediate Similarity	NPC38468
0.7579	Intermediate Similarity	NPC50362
0.7579	Intermediate Similarity	NPC319795
0.7576	Intermediate Similarity	NPC228451
0.7576	Intermediate Similarity	NPC473234
0.7576	Intermediate Similarity	NPC473263
0.7576	Intermediate Similarity	NPC125674
0.7576	Intermediate Similarity	NPC475838
0.7576	Intermediate Similarity	NPC473273
0.7576	Intermediate Similarity	NPC308656
0.7576	Intermediate Similarity	NPC60386
0.7573	Intermediate Similarity	NPC474742
0.7573	Intermediate Similarity	NPC171759
0.757	Intermediate Similarity	NPC477102
0.7553	Intermediate Similarity	NPC475947
0.7553	Intermediate Similarity	NPC245665
0.7553	Intermediate Similarity	NPC474472
0.7553	Intermediate Similarity	NPC128429
0.7553	Intermediate Similarity	NPC250315
0.7553	Intermediate Similarity	NPC257358
0.7551	Intermediate Similarity	NPC179394
0.7551	Intermediate Similarity	NPC475855
0.7551	Intermediate Similarity	NPC474761
0.7551	Intermediate Similarity	NPC476004
0.7551	Intermediate Similarity	NPC129419
0.7551	Intermediate Similarity	NPC144133

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 NPC224689 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	285
0.1-0.2	2515
0.2-0.3	3977
0.3-0.4	1714
0.4-0.5	439
0.5-0.6	191
0.6-0.7	27
0.7-0.8	2
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
0.8191	Intermediate Similarity	NPD1695	Approved
0.8058	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7579	Intermediate Similarity	NPD1733	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6371	Approved
0.703	Intermediate Similarity	NPD46	Approved
0.703	Intermediate Similarity	NPD6698	Approved
0.697	Remote Similarity	NPD4249	Approved
0.6923	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6903	Remote Similarity	NPD6053	Discontinued
0.69	Remote Similarity	NPD4251	Approved
0.69	Remote Similarity	NPD4250	Approved
0.67	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6699	Remote Similarity	NPD7838	Discovery
0.6699	Remote Similarity	NPD5785	Approved
0.6667	Remote Similarity	NPD5362	Discontinued
0.6667	Remote Similarity	NPD6008	Approved
0.6566	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6549	Remote Similarity	NPD6686	Approved
0.6535	Remote Similarity	NPD1694	Approved
0.6535	Remote Similarity	NPD5363	Approved
0.6531	Remote Similarity	NPD4822	Approved
0.6531	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6531	Remote Similarity	NPD4821	Approved
0.6531	Remote Similarity	NPD4820	Approved
0.6531	Remote Similarity	NPD4819	Approved
0.6522	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6509	Remote Similarity	NPD5282	Discontinued
0.65	Remote Similarity	NPD7154	Phase 3
0.6476	Remote Similarity	NPD7983	Approved
0.6465	Remote Similarity	NPD5369	Approved
0.646	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6422	Remote Similarity	NPD4225	Approved
0.6422	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.64	Remote Similarity	NPD4269	Approved
0.64	Remote Similarity	NPD6435	Approved
0.64	Remote Similarity	NPD4270	Approved
0.6364	Remote Similarity	NPD6648	Approved
0.6327	Remote Similarity	NPD4271	Approved
0.6327	Remote Similarity	NPD4268	Approved
0.6311	Remote Similarity	NPD5786	Approved
0.6306	Remote Similarity	NPD5344	Discontinued
0.6293	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6273	Remote Similarity	NPD7638	Approved
0.624	Remote Similarity	NPD7507	Approved
0.6238	Remote Similarity	NPD5209	Approved
0.6216	Remote Similarity	NPD7639	Approved
0.6216	Remote Similarity	NPD7640	Approved
0.6207	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.62	Remote Similarity	NPD5368	Approved
0.62	Remote Similarity	NPD4252	Approved
0.619	Remote Similarity	NPD6903	Approved
0.6176	Remote Similarity	NPD5331	Approved
0.6176	Remote Similarity	NPD5332	Approved
0.6168	Remote Similarity	NPD5693	Phase 1
0.616	Remote Similarity	NPD7492	Approved
0.6154	Remote Similarity	NPD7521	Approved
0.6154	Remote Similarity	NPD7334	Approved
0.6154	Remote Similarity	NPD6409	Approved
0.6154	Remote Similarity	NPD7146	Approved
0.6154	Remote Similarity	NPD5330	Approved
0.6154	Remote Similarity	NPD6684	Approved
0.6147	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6139	Remote Similarity	NPD4790	Discontinued
0.6116	Remote Similarity	NPD7115	Discovery
0.6111	Remote Similarity	NPD5779	Approved
0.6111	Remote Similarity	NPD5778	Approved
0.6111	Remote Similarity	NPD6616	Approved
0.6098	Remote Similarity	NPD6319	Approved
0.6098	Remote Similarity	NPD6054	Approved
0.6094	Remote Similarity	NPD7319	Approved
0.6087	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6075	Remote Similarity	NPD5207	Approved
0.6063	Remote Similarity	NPD7078	Approved
0.6048	Remote Similarity	NPD6015	Approved
0.6048	Remote Similarity	NPD8516	Approved
0.6048	Remote Similarity	NPD8517	Approved
0.6048	Remote Similarity	NPD6016	Approved
0.6048	Remote Similarity	NPD8513	Phase 3
0.6048	Remote Similarity	NPD8515	Approved
0.6038	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6034	Remote Similarity	NPD6412	Phase 2
0.6016	Remote Similarity	NPD7736	Approved
0.6	Remote Similarity	NPD4632	Approved
0.6	Remote Similarity	NPD5695	Phase 3
0.6	Remote Similarity	NPD6370	Approved
0.6	Remote Similarity	NPD5988	Approved
0.5982	Remote Similarity	NPD5696	Approved
0.5981	Remote Similarity	NPD6051	Approved
0.5968	Remote Similarity	NPD6059	Approved
0.5963	Remote Similarity	NPD6399	Phase 3
0.5938	Remote Similarity	NPD8293	Discontinued
0.5935	Remote Similarity	NPD7327	Approved
0.5935	Remote Similarity	NPD7328	Approved
0.592	Remote Similarity	NPD8033	Approved
0.5917	Remote Similarity	NPD8297	Approved
0.5909	Remote Similarity	NPD6001	Approved
0.5897	Remote Similarity	NPD5697	Approved
0.5893	Remote Similarity	NPD6084	Phase 2
0.5893	Remote Similarity	NPD6083	Phase 2
0.5887	Remote Similarity	NPD7516	Approved
0.5859	Remote Similarity	NPD8039	Approved
0.5854	Remote Similarity	NPD6009	Approved
0.5847	Remote Similarity	NPD6881	Approved
0.5847	Remote Similarity	NPD6899	Approved
0.5847	Remote Similarity	NPD7320	Approved
0.5842	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.584	Remote Similarity	NPD8294	Approved
0.584	Remote Similarity	NPD8377	Approved
0.5833	Remote Similarity	NPD6650	Approved
0.5833	Remote Similarity	NPD6649	Approved
0.5833	Remote Similarity	NPD6080	Approved
0.5833	Remote Similarity	NPD6673	Approved
0.5833	Remote Similarity	NPD6904	Approved
0.5833	Remote Similarity	NPD6845	Suspended
0.5826	Remote Similarity	NPD7632	Discontinued
0.5814	Remote Similarity	NPD8074	Phase 3
0.5812	Remote Similarity	NPD6675	Approved
0.5812	Remote Similarity	NPD7128	Approved
0.5812	Remote Similarity	NPD5739	Approved
0.5812	Remote Similarity	NPD6402	Approved
0.5798	Remote Similarity	NPD6014	Approved
0.5798	Remote Similarity	NPD6373	Approved
0.5798	Remote Similarity	NPD6013	Approved
0.5798	Remote Similarity	NPD6012	Approved
0.5798	Remote Similarity	NPD6372	Approved
0.5794	Remote Similarity	NPD5983	Phase 2
0.5794	Remote Similarity	NPD8296	Approved
0.5794	Remote Similarity	NPD8380	Approved
0.5794	Remote Similarity	NPD8378	Approved
0.5794	Remote Similarity	NPD7503	Approved
0.5794	Remote Similarity	NPD8335	Approved
0.5794	Remote Similarity	NPD8379	Approved
0.578	Remote Similarity	NPD5692	Phase 3
0.5763	Remote Similarity	NPD5701	Approved
0.5758	Remote Similarity	NPD7260	Phase 2
0.575	Remote Similarity	NPD6883	Approved
0.575	Remote Similarity	NPD7102	Approved
0.575	Remote Similarity	NPD7290	Approved
0.5741	Remote Similarity	NPD6672	Approved
0.5741	Remote Similarity	NPD5208	Approved
0.5741	Remote Similarity	NPD5737	Approved
0.5738	Remote Similarity	NPD8133	Approved
0.5727	Remote Similarity	NPD6050	Approved
0.5727	Remote Similarity	NPD5284	Approved
0.5727	Remote Similarity	NPD5281	Approved
0.5727	Remote Similarity	NPD7637	Suspended
0.5727	Remote Similarity	NPD5694	Approved
0.5714	Remote Similarity	NPD6011	Approved
0.5703	Remote Similarity	NPD7604	Phase 2
0.5702	Remote Similarity	NPD6847	Approved
0.5702	Remote Similarity	NPD2204	Approved
0.5702	Remote Similarity	NPD8130	Phase 1
0.5702	Remote Similarity	NPD6617	Approved
0.5702	Remote Similarity	NPD6869	Approved
0.5701	Remote Similarity	NPD6098	Approved
0.5688	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.5688	Remote Similarity	NPD6101	Approved
0.5682	Remote Similarity	NPD5956	Approved
0.5664	Remote Similarity	NPD7839	Suspended
0.5662	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.5656	Remote Similarity	NPD6882	Approved
0.5641	Remote Similarity	NPD6052	Approved
0.5625	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.5625	Remote Similarity	NPD7900	Approved
0.562	Remote Similarity	NPD4634	Approved
0.562	Remote Similarity	NPD2067	Discontinued
0.5615	Remote Similarity	NPD8273	Phase 1
0.5615	Remote Similarity	NPD6336	Discontinued

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