NPASS Compound

Structure

NPC304445 OpenBabel07101719152D 30 33 0 0 1 0 0 0 0 0999 V2000 3.4159 3.3156 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7059 -0.9404 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7020 1.1858 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0449 2.8529 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7247 1.4539 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7319 0.0259 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0850 2.5725 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5126 0.0407 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7885 0.7791 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.7058 1.6472 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.8626 2.2773 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.6053 0.4611 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8584 0.5129 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.1928 0.7738 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.9224 1.2791 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8435 1.5128 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0299 1.9998 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8884 1.4869 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.1793 0.6100 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 6.5805 -0.1991 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8734 0.4870 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7468 -0.9740 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.7360 2.7643 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7019 2.0257 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0449 2.9997 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7618 1.9739 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.2497 -0.9422 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7319 -0.0259 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 5.5860 -0.3036 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 7 2 0 0 0 0 2 8 2 0 0 0 0 4 7 1 0 0 0 0 4 11 1 0 0 0 0 5 12 1 0 0 0 0 6 22 1 0 0 0 0 7 10 1 0 0 0 0 8 12 1 0 0 0 0 9 3 1 6 0 0 0 9 15 1 0 0 0 0 9 20 1 0 0 0 0 10 5 1 1 0 0 0 10 14 1 0 0 0 0 11 15 1 0 0 0 0 11 23 1 1 0 0 0 12 28 1 1 0 0 0 13 6 1 6 0 0 0 13 16 1 0 0 0 0 13 29 1 0 0 0 0 14 8 1 1 0 0 0 14 19 1 0 0 0 0 15 19 1 0 0 0 0 16 17 1 0 0 0 0 16 24 1 0 0 0 0 17 18 1 0 0 0 0 17 25 1 0 0 0 0 18 21 1 0 0 0 0 18 26 1 0 0 0 0 19 30 1 0 0 0 0 20 27 2 0 0 0 0 20 30 1 0 0 0 0 21 28 1 0 0 0 0 21 29 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	426.19
Volume:	408.749
LogP:	-0.113
LogD:	0.195
LogS:	-1.61
# Rotatable Bonds:	3
TPSA:	145.91
# H-Bond Aceptor:	9
# H-Bond Donor:	5
# Rings:	4
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.279
Synthetic Accessibility Score:	5.203
Fsp3:	0.762
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:	-6.28
MDCK Permeability:	0.00010180455137742683
Pgp-inhibitor:	0.001
Pgp-substrate:	0.894
Human Intestinal Absorption (HIA):	0.565
20% Bioavailability (F20%):	0.113
30% Bioavailability (F30%):	0.859

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.094
Plasma Protein Binding (PPB):	49.75666427612305%
Volume Distribution (VD):	0.522
Pgp-substrate:	54.414058685302734%

ADMET: Metabolism

CYP1A2-inhibitor:	0.015
CYP1A2-substrate:	0.064
CYP2C19-inhibitor:	0.012
CYP2C19-substrate:	0.475
CYP2C9-inhibitor:	0.001
CYP2C9-substrate:	0.032
CYP2D6-inhibitor:	0.003
CYP2D6-substrate:	0.092
CYP3A4-inhibitor:	0.012
CYP3A4-substrate:	0.063

ADMET: Excretion

Clearance (CL):	1.711
Half-life (T1/2):	0.664

ADMET: Toxicity

hERG Blockers:	0.14
Human Hepatotoxicity (H-HT):	0.94
Drug-inuced Liver Injury (DILI):	0.653
AMES Toxicity:	0.127
Rat Oral Acute Toxicity:	0.219
Maximum Recommended Daily Dose:	0.531
Skin Sensitization:	0.049
Carcinogencity:	0.06
Eye Corrosion:	0.003
Eye Irritation:	0.012
Respiratory Toxicity:	0.942

Download Data

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

Natural Product: NPC304445

Natural Product ID:	NPC304445
*Common Name:**	ALFNDZUCKXOXII-ZMFKIYIOSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	ALFNDZUCKXOXII-ZMFKIYIOSA-N
Standard InCHI:	InChI=1S/C21H30O9/c1-7-4-11(23)15-9(3)20(27)30-19(15)14-8(2)12(5-10(7)14)28-21-18(26)17(25)16(24)13(6-22)29-21/h9-19,21-26H,1-2,4-6H2,3H3/t9-,10-,11+,12-,13+,14-,15+,16+,17-,18+,19+,21+/m0/s1
SMILES:	C=C1C[C@H]([C@H]2[C@H](C)C(=O)O[C@@H]2[C@H]2C(=C)[C@H](C[C@@H]12)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3622763
PubChem CID:	n.a.
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:0001770] Guaianolides 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
NPO32813	ixeris dentata	Species	Asteraceae	Eukaryota	Roots	n.a.	n.a.	PMID[26341134]

☑ 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
Others	4

Activity Type	# Activity
NON-MOLECULAR	2
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	20.4	uM	PMID[463149]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	18.0	uM	PMID[463149]
NPT27	Others	Unspecified		Activity	=	105.5	%	PMID[463149]
NPT27	Others	Unspecified		Activity	=	104.9	%	PMID[463149]

☑ 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 NPC304445 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	231
0.1-0.2	1581
0.2-0.3	5905
0.3-0.4	13345
0.4-0.5	9563
0.5-0.6	7284
0.6-0.7	4261
0.7-0.8	463
0.8-0.85	51
0.85-0.9	1
0.9-0.95	5
0.95-1	7

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC236580
0.9677	High Similarity	NPC67296
0.9674	High Similarity	NPC49833
0.9674	High Similarity	NPC249171
0.967	High Similarity	NPC474297
0.9474	High Similarity	NPC473148
0.9368	High Similarity	NPC80144
0.9355	High Similarity	NPC58267
0.9355	High Similarity	NPC261372
0.9355	High Similarity	NPC263674
0.914	High Similarity	NPC167893
0.8763	High Similarity	NPC473146
0.8687	High Similarity	NPC475928
0.8515	High Similarity	NPC170432
0.8495	Intermediate Similarity	NPC217983
0.8495	Intermediate Similarity	NPC207114
0.8469	Intermediate Similarity	NPC472015
0.8431	Intermediate Similarity	NPC197813
0.8431	Intermediate Similarity	NPC148270
0.8431	Intermediate Similarity	NPC80338
0.84	Intermediate Similarity	NPC4899
0.84	Intermediate Similarity	NPC474730
0.84	Intermediate Similarity	NPC35185
0.84	Intermediate Similarity	NPC177013
0.84	Intermediate Similarity	NPC106668
0.8367	Intermediate Similarity	NPC474313
0.8367	Intermediate Similarity	NPC471150
0.8352	Intermediate Similarity	NPC128246
0.8351	Intermediate Similarity	NPC472873
0.8333	Intermediate Similarity	NPC475788
0.8317	Intermediate Similarity	NPC37240
0.8317	Intermediate Similarity	NPC27687
0.8316	Intermediate Similarity	NPC297474
0.8316	Intermediate Similarity	NPC19087
0.8316	Intermediate Similarity	NPC54065
0.8298	Intermediate Similarity	NPC470009
0.828	Intermediate Similarity	NPC187661
0.8265	Intermediate Similarity	NPC54731
0.8229	Intermediate Similarity	NPC171360
0.8229	Intermediate Similarity	NPC57304
0.8229	Intermediate Similarity	NPC35959
0.8229	Intermediate Similarity	NPC133888
0.8229	Intermediate Similarity	NPC475925
0.8229	Intermediate Similarity	NPC29821
0.8229	Intermediate Similarity	NPC235051
0.8229	Intermediate Similarity	NPC184063
0.8229	Intermediate Similarity	NPC63193
0.8229	Intermediate Similarity	NPC293001
0.8211	Intermediate Similarity	NPC38392
0.8211	Intermediate Similarity	NPC155935
0.8211	Intermediate Similarity	NPC215556
0.819	Intermediate Similarity	NPC193741
0.8182	Intermediate Similarity	NPC472290
0.8173	Intermediate Similarity	NPC110701
0.8163	Intermediate Similarity	NPC6765
0.8163	Intermediate Similarity	NPC93869
0.8155	Intermediate Similarity	NPC127235
0.8152	Intermediate Similarity	NPC111409
0.8132	Intermediate Similarity	NPC126248
0.8125	Intermediate Similarity	NPC206614
0.8125	Intermediate Similarity	NPC216284
0.8125	Intermediate Similarity	NPC35809
0.8125	Intermediate Similarity	NPC474323
0.8119	Intermediate Similarity	NPC287539
0.8119	Intermediate Similarity	NPC3488
0.8105	Intermediate Similarity	NPC79549
0.81	Intermediate Similarity	NPC37866
0.8085	Intermediate Similarity	NPC304558
0.8081	Intermediate Similarity	NPC161293
0.8081	Intermediate Similarity	NPC306041
0.8065	Intermediate Similarity	NPC224386
0.8065	Intermediate Similarity	NPC194859
0.8061	Intermediate Similarity	NPC274588
0.8043	Intermediate Similarity	NPC246076
0.8037	Intermediate Similarity	NPC475924
0.8037	Intermediate Similarity	NPC475851
0.802	Intermediate Similarity	NPC186861
0.802	Intermediate Similarity	NPC471381
0.8	Intermediate Similarity	NPC311904
0.7982	Intermediate Similarity	NPC277583
0.7921	Intermediate Similarity	NPC45125
0.7917	Intermediate Similarity	NPC471149
0.79	Intermediate Similarity	NPC91771
0.79	Intermediate Similarity	NPC24956
0.79	Intermediate Similarity	NPC142529
0.79	Intermediate Similarity	NPC170527
0.79	Intermediate Similarity	NPC18019
0.79	Intermediate Similarity	NPC476009
0.7895	Intermediate Similarity	NPC56593
0.7857	Intermediate Similarity	NPC472197
0.7857	Intermediate Similarity	NPC155215
0.7835	Intermediate Similarity	NPC92974
0.7835	Intermediate Similarity	NPC283409
0.7822	Intermediate Similarity	NPC181151
0.7812	Intermediate Similarity	NPC190753
0.7812	Intermediate Similarity	NPC118601
0.7812	Intermediate Similarity	NPC475773
0.7812	Intermediate Similarity	NPC24728
0.7812	Intermediate Similarity	NPC186148
0.781	Intermediate Similarity	NPC44004
0.781	Intermediate Similarity	NPC54737
0.78	Intermediate Similarity	NPC476053
0.78	Intermediate Similarity	NPC163228
0.78	Intermediate Similarity	NPC213698
0.7789	Intermediate Similarity	NPC204105
0.7789	Intermediate Similarity	NPC284534
0.7789	Intermediate Similarity	NPC300082
0.7778	Intermediate Similarity	NPC320089
0.7778	Intermediate Similarity	NPC258216
0.7767	Intermediate Similarity	NPC216911
0.7767	Intermediate Similarity	NPC150923
0.7757	Intermediate Similarity	NPC139838
0.7757	Intermediate Similarity	NPC59489
0.7755	Intermediate Similarity	NPC246173
0.7732	Intermediate Similarity	NPC178875
0.7732	Intermediate Similarity	NPC177629
0.7732	Intermediate Similarity	NPC58219
0.7723	Intermediate Similarity	NPC284063
0.7714	Intermediate Similarity	NPC474917
0.7708	Intermediate Similarity	NPC64153
0.7708	Intermediate Similarity	NPC162071
0.7708	Intermediate Similarity	NPC236692
0.7708	Intermediate Similarity	NPC309757
0.77	Intermediate Similarity	NPC63897
0.77	Intermediate Similarity	NPC473331
0.77	Intermediate Similarity	NPC127019
0.77	Intermediate Similarity	NPC198853
0.7692	Intermediate Similarity	NPC94919
0.7692	Intermediate Similarity	NPC261117
0.7692	Intermediate Similarity	NPC86077
0.7692	Intermediate Similarity	NPC310804
0.7685	Intermediate Similarity	NPC106760
0.7677	Intermediate Similarity	NPC131209
0.7677	Intermediate Similarity	NPC9447
0.7677	Intermediate Similarity	NPC133698
0.767	Intermediate Similarity	NPC476320
0.767	Intermediate Similarity	NPC70865
0.767	Intermediate Similarity	NPC476211
0.7664	Intermediate Similarity	NPC475960
0.7664	Intermediate Similarity	NPC68248
0.7664	Intermediate Similarity	NPC224414
0.7653	Intermediate Similarity	NPC472872
0.7647	Intermediate Similarity	NPC86843
0.7647	Intermediate Similarity	NPC161493
0.7636	Intermediate Similarity	NPC293658
0.7636	Intermediate Similarity	NPC474410
0.7634	Intermediate Similarity	NPC156658
0.7634	Intermediate Similarity	NPC51507
0.7634	Intermediate Similarity	NPC258965
0.7624	Intermediate Similarity	NPC67584
0.7624	Intermediate Similarity	NPC170120
0.7624	Intermediate Similarity	NPC52044
0.7624	Intermediate Similarity	NPC475900
0.7619	Intermediate Similarity	NPC329834
0.7615	Intermediate Similarity	NPC471251
0.7611	Intermediate Similarity	NPC477071
0.76	Intermediate Similarity	NPC473263
0.76	Intermediate Similarity	NPC308656
0.76	Intermediate Similarity	NPC473273
0.76	Intermediate Similarity	NPC473234
0.76	Intermediate Similarity	NPC60386
0.76	Intermediate Similarity	NPC472874
0.76	Intermediate Similarity	NPC470187
0.76	Intermediate Similarity	NPC200237
0.7596	Intermediate Similarity	NPC473332
0.7596	Intermediate Similarity	NPC476230
0.7596	Intermediate Similarity	NPC27474
0.7596	Intermediate Similarity	NPC171759
0.7579	Intermediate Similarity	NPC245665
0.7573	Intermediate Similarity	NPC187268
0.757	Intermediate Similarity	NPC293512
0.757	Intermediate Similarity	NPC26617
0.7549	Intermediate Similarity	NPC213078
0.7544	Intermediate Similarity	NPC142882
0.7526	Intermediate Similarity	NPC476015
0.7526	Intermediate Similarity	NPC475019
0.7526	Intermediate Similarity	NPC474762
0.7526	Intermediate Similarity	NPC470242
0.7526	Intermediate Similarity	NPC474949
0.7526	Intermediate Similarity	NPC470657
0.7525	Intermediate Similarity	NPC477131
0.7525	Intermediate Similarity	NPC262133
0.7525	Intermediate Similarity	NPC71589
0.7525	Intermediate Similarity	NPC470013
0.7525	Intermediate Similarity	NPC472198
0.7525	Intermediate Similarity	NPC470010
0.7525	Intermediate Similarity	NPC190294
0.7525	Intermediate Similarity	NPC323008
0.7524	Intermediate Similarity	NPC304163
0.7524	Intermediate Similarity	NPC250545
0.7523	Intermediate Similarity	NPC114961
0.7523	Intermediate Similarity	NPC124053
0.7523	Intermediate Similarity	NPC27551
0.75	Intermediate Similarity	NPC66504
0.75	Intermediate Similarity	NPC130792
0.75	Intermediate Similarity	NPC219900
0.75	Intermediate Similarity	NPC191339
0.75	Intermediate Similarity	NPC288471
0.75	Intermediate Similarity	NPC12172
0.75	Intermediate Similarity	NPC177524

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 NPC304445 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	2266
0.2-0.3	3913
0.3-0.4	1850
0.4-0.5	538
0.5-0.6	284
0.6-0.7	71
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
0.757	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6686	Approved
0.7477	Intermediate Similarity	NPD8133	Approved
0.74	Intermediate Similarity	NPD46	Approved
0.74	Intermediate Similarity	NPD6698	Approved
0.7297	Intermediate Similarity	NPD8413	Clinical (unspecified phase)
0.7129	Intermediate Similarity	NPD1695	Approved
0.7091	Intermediate Similarity	NPD6412	Phase 2
0.7083	Intermediate Similarity	NPD7507	Approved
0.7034	Intermediate Similarity	NPD8515	Approved
0.7034	Intermediate Similarity	NPD8516	Approved
0.7034	Intermediate Similarity	NPD8517	Approved
0.7034	Intermediate Similarity	NPD8513	Phase 3
0.6911	Remote Similarity	NPD7319	Approved
0.6903	Remote Similarity	NPD6371	Approved
0.6832	Remote Similarity	NPD4249	Approved
0.6792	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.678	Remote Similarity	NPD7327	Approved
0.678	Remote Similarity	NPD7328	Approved
0.6765	Remote Similarity	NPD4250	Approved
0.6765	Remote Similarity	NPD4251	Approved
0.6759	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.675	Remote Similarity	NPD8033	Approved
0.6723	Remote Similarity	NPD7516	Approved
0.6667	Remote Similarity	NPD8377	Approved
0.6667	Remote Similarity	NPD8294	Approved
0.6667	Remote Similarity	NPD7983	Approved
0.6667	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6638	Remote Similarity	NPD6053	Discontinued
0.6612	Remote Similarity	NPD8269	Approved
0.6612	Remote Similarity	NPD8378	Approved
0.6612	Remote Similarity	NPD8296	Approved
0.6612	Remote Similarity	NPD8380	Approved
0.6612	Remote Similarity	NPD8335	Approved
0.6612	Remote Similarity	NPD8266	Approved
0.6612	Remote Similarity	NPD8268	Approved
0.6612	Remote Similarity	NPD8267	Approved
0.6612	Remote Similarity	NPD8379	Approved
0.6607	Remote Similarity	NPD4056	Clinical (unspecified phase)
0.6607	Remote Similarity	NPD4057	Clinical (unspecified phase)
0.6571	Remote Similarity	NPD7838	Discovery
0.6569	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6535	Remote Similarity	NPD5362	Discontinued
0.648	Remote Similarity	NPD8074	Phase 3
0.6475	Remote Similarity	NPD7503	Approved
0.646	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6436	Remote Similarity	NPD6435	Approved
0.6417	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6408	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.64	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.64	Remote Similarity	NPD8451	Approved
0.6389	Remote Similarity	NPD5282	Discontinued
0.6373	Remote Similarity	NPD7154	Phase 3
0.6364	Remote Similarity	NPD4238	Approved
0.6364	Remote Similarity	NPD7641	Discontinued
0.6364	Remote Similarity	NPD4802	Phase 2
0.6349	Remote Similarity	NPD8293	Discontinued
0.6349	Remote Similarity	NPD8448	Approved
0.6341	Remote Similarity	NPD8444	Approved
0.6337	Remote Similarity	NPD5369	Approved
0.6306	Remote Similarity	NPD7638	Approved
0.6306	Remote Similarity	NPD4225	Approved
0.6299	Remote Similarity	NPD7736	Approved
0.6293	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.629	Remote Similarity	NPD6370	Approved
0.6281	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.6275	Remote Similarity	NPD4270	Approved
0.6275	Remote Similarity	NPD4269	Approved
0.6273	Remote Similarity	NPD7839	Suspended
0.6262	Remote Similarity	NPD5785	Approved
0.625	Remote Similarity	NPD7640	Approved
0.625	Remote Similarity	NPD7639	Approved
0.624	Remote Similarity	NPD7829	Approved
0.624	Remote Similarity	NPD7642	Approved
0.624	Remote Similarity	NPD8328	Phase 3
0.624	Remote Similarity	NPD7830	Approved
0.6238	Remote Similarity	NPD5368	Approved
0.6238	Remote Similarity	NPD4821	Approved
0.6238	Remote Similarity	NPD4819	Approved
0.6238	Remote Similarity	NPD4822	Approved
0.6238	Remote Similarity	NPD4820	Approved
0.6214	Remote Similarity	NPD3669	Approved
0.6214	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.6202	Remote Similarity	NPD8391	Approved
0.6202	Remote Similarity	NPD8392	Approved
0.6202	Remote Similarity	NPD8390	Approved
0.62	Remote Similarity	NPD4268	Approved
0.62	Remote Similarity	NPD4271	Approved
0.619	Remote Similarity	NPD8340	Approved
0.619	Remote Similarity	NPD5786	Approved
0.619	Remote Similarity	NPD8341	Approved
0.619	Remote Similarity	NPD8299	Approved
0.619	Remote Similarity	NPD8342	Approved
0.619	Remote Similarity	NPD7492	Approved
0.6147	Remote Similarity	NPD6399	Phase 3
0.6147	Remote Similarity	NPD5779	Approved
0.6147	Remote Similarity	NPD5778	Approved
0.6142	Remote Similarity	NPD6616	Approved
0.6129	Remote Similarity	NPD6054	Approved
0.6129	Remote Similarity	NPD6059	Approved
0.6111	Remote Similarity	NPD6067	Discontinued
0.6102	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6095	Remote Similarity	NPD5363	Approved
0.6094	Remote Similarity	NPD7078	Approved
0.608	Remote Similarity	NPD8274	Clinical (unspecified phase)
0.608	Remote Similarity	NPD6016	Approved
0.608	Remote Similarity	NPD6015	Approved
0.6078	Remote Similarity	NPD4252	Approved
0.6058	Remote Similarity	NPD5332	Approved
0.6058	Remote Similarity	NPD5331	Approved
0.6055	Remote Similarity	NPD8035	Phase 2
0.6055	Remote Similarity	NPD8034	Phase 2
0.6053	Remote Similarity	NPD5344	Discontinued
0.605	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6045	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6032	Remote Similarity	NPD5988	Approved
0.6032	Remote Similarity	NPD8080	Discontinued
0.6019	Remote Similarity	NPD6101	Approved
0.6019	Remote Similarity	NPD1780	Approved
0.6019	Remote Similarity	NPD4790	Discontinued
0.6019	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6019	Remote Similarity	NPD1779	Approved
0.6016	Remote Similarity	NPD7115	Discovery
0.6016	Remote Similarity	NPD8273	Phase 1
0.6016	Remote Similarity	NPD6009	Approved
0.6	Remote Similarity	NPD8084	Approved
0.6	Remote Similarity	NPD8085	Approved
0.6	Remote Similarity	NPD8171	Discontinued
0.6	Remote Similarity	NPD8138	Approved
0.6	Remote Similarity	NPD8082	Approved
0.6	Remote Similarity	NPD8086	Approved
0.6	Remote Similarity	NPD6319	Approved
0.6	Remote Similarity	NPD8139	Approved
0.6	Remote Similarity	NPD8083	Approved
0.5983	Remote Similarity	NPD6008	Approved
0.595	Remote Similarity	NPD6882	Approved
0.5948	Remote Similarity	NPD8276	Approved
0.5948	Remote Similarity	NPD8275	Approved
0.5923	Remote Similarity	NPD8336	Approved
0.5923	Remote Similarity	NPD8337	Approved
0.5909	Remote Similarity	NPD7637	Suspended
0.5909	Remote Similarity	NPD6411	Approved
0.5902	Remote Similarity	NPD4632	Approved
0.5897	Remote Similarity	NPD8081	Approved
0.5882	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.5865	Remote Similarity	NPD6845	Suspended
0.5862	Remote Similarity	NPD7632	Discontinued
0.5849	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.5847	Remote Similarity	NPD8393	Approved
0.5833	Remote Similarity	NPD896	Approved
0.5833	Remote Similarity	NPD6373	Approved
0.5833	Remote Similarity	NPD6372	Approved
0.5833	Remote Similarity	NPD897	Approved
0.5833	Remote Similarity	NPD7524	Approved
0.5833	Remote Similarity	NPD898	Approved
0.5827	Remote Similarity	NPD6921	Approved
0.582	Remote Similarity	NPD8297	Approved
0.5816	Remote Similarity	NPD7532	Clinical (unspecified phase)
0.5798	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.5794	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.5789	Remote Similarity	NPD7260	Phase 2
0.5789	Remote Similarity	NPD6083	Phase 2
0.5789	Remote Similarity	NPD6084	Phase 2
0.5761	Remote Similarity	NPD3198	Approved
0.5752	Remote Similarity	NPD5695	Phase 3
0.575	Remote Similarity	NPD7320	Approved
0.5746	Remote Similarity	NPD8338	Approved
0.5739	Remote Similarity	NPD5696	Approved
0.5738	Remote Similarity	NPD6650	Approved
0.5738	Remote Similarity	NPD6649	Approved
0.5736	Remote Similarity	NPD7122	Discontinued
0.5714	Remote Similarity	NPD5956	Approved
0.5714	Remote Similarity	NPD7128	Approved
0.5714	Remote Similarity	NPD6675	Approved
0.5714	Remote Similarity	NPD5739	Approved
0.5714	Remote Similarity	NPD6402	Approved
0.5702	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.5701	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.569	Remote Similarity	NPD6648	Approved
0.5684	Remote Similarity	NPD7909	Approved
0.5682	Remote Similarity	NPD6033	Approved
0.568	Remote Similarity	NPD6940	Discontinued
0.5667	Remote Similarity	NPD8140	Approved
0.5667	Remote Similarity	NPD6685	Approved
0.5667	Remote Similarity	NPD8307	Discontinued
0.5667	Remote Similarity	NPD5697	Approved
0.5667	Remote Similarity	NPD5701	Approved
0.566	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.566	Remote Similarity	NPD3667	Approved
0.5656	Remote Similarity	NPD6421	Discontinued
0.5648	Remote Similarity	NPD1694	Approved
0.5641	Remote Similarity	NPD1700	Approved
0.5636	Remote Similarity	NPD6903	Approved
0.562	Remote Similarity	NPD6899	Approved
0.562	Remote Similarity	NPD6881	Approved
0.5607	Remote Similarity	NPD6695	Phase 3
0.5604	Remote Similarity	NPD2267	Suspended

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