NPASS Compound

Structure

NPC472998 OpenBabel07101719252D 33 35 0 0 1 0 0 0 0 0999 V2000 2.5981 -2.5000 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 2.5981 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 3.5000 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 5.9603 1.2569 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8558 2.2514 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 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5686 1.0055 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 2.5981 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 4.0000 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 3.4641 2.0000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 4.5468 0.7976 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 1.7321 2.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8660 2.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 2.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 2 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 5.0468 1.6636 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 5.0000 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 4.9535 -0.1160 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 3.5000 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 2.5981 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3776 2.4067 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 1 0 0 0 0 2 11 1 0 0 0 0 3 12 2 0 0 0 0 4 13 1 0 0 0 0 5 14 1 0 0 0 0 6 23 1 0 0 0 0 7 23 1 0 0 0 0 9 11 2 0 0 0 0 10 15 1 0 0 0 0 10 16 1 0 0 0 0 11 22 1 0 0 0 0 12 15 1 0 0 0 0 13 25 2 0 0 0 0 13 29 1 0 0 0 0 14 26 2 0 0 0 0 14 30 1 0 0 0 0 15 32 1 0 0 0 0 16 23 1 0 0 0 0 16 27 1 0 0 0 0 17 12 1 1 0 0 0 17 18 1 0 0 0 0 17 19 1 0 0 0 0 18 20 1 0 0 0 0 18 29 1 1 0 0 0 19 21 1 0 0 0 0 19 31 1 6 0 0 0 20 24 1 1 0 0 0 20 30 1 0 0 0 0 21 24 1 6 0 0 0 21 33 1 0 0 0 0 22 28 2 0 0 0 0 22 31 1 0 0 0 0 23 32 1 0 0 0 0 24 8 1 6 0 0 0 24 33 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	466.22
Volume:	463.92
LogP:	1.603
LogD:	1.29
LogS:	-3.12
# Rotatable Bonds:	9
TPSA:	120.89
# H-Bond Aceptor:	9
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.206
Synthetic Accessibility Score:	5.242
Fsp3:	0.708
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:	-4.926
MDCK Permeability:	7.743018795736134e-05
Pgp-inhibitor:	0.995
Pgp-substrate:	0.027
Human Intestinal Absorption (HIA):	0.879
20% Bioavailability (F20%):	0.023
30% Bioavailability (F30%):	0.994

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.272
Plasma Protein Binding (PPB):	32.040122985839844%
Volume Distribution (VD):	1.707
Pgp-substrate:	44.25200653076172%

ADMET: Metabolism

CYP1A2-inhibitor:	0.023
CYP1A2-substrate:	0.047
CYP2C19-inhibitor:	0.019
CYP2C19-substrate:	0.372
CYP2C9-inhibitor:	0.03
CYP2C9-substrate:	0.021
CYP2D6-inhibitor:	0.483
CYP2D6-substrate:	0.119
CYP3A4-inhibitor:	0.444
CYP3A4-substrate:	0.353

ADMET: Excretion

Clearance (CL):	6.394
Half-life (T1/2):	0.508

ADMET: Toxicity

hERG Blockers:	0.182
Human Hepatotoxicity (H-HT):	0.985
Drug-inuced Liver Injury (DILI):	0.83
AMES Toxicity:	0.04
Rat Oral Acute Toxicity:	0.603
Maximum Recommended Daily Dose:	0.037
Skin Sensitization:	0.143
Carcinogencity:	0.033
Eye Corrosion:	0.013
Eye Irritation:	0.015
Respiratory Toxicity:	0.978

Download Data

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

Natural Product: NPC472998

Natural Product ID:	NPC472998
*Common Name:**	LEJGPTQNKIOPDG-RWPQZSAASA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	LEJGPTQNKIOPDG-RWPQZSAASA-N
Standard InCHI:	InChI=1S/C24H34O9/c1-9-11(2)22(28)31-19-17(12(3)15-10-16(27)23(6,7)32-15)18(29-13(4)25)20(30-14(5)26)24(8)21(19)33-24/h9,15-21,27H,3,10H2,1-2,4-8H3/b11-9-/t15?,16?,17-,18+,19+,20+,21-,24+/m1/s1
SMILES:	C/C=C(C(=O)O[C@H]1[C@H](C(=C)C2CC(C(O2)(C)C)O)[C@H](OC(=O)C)[C@@H]([C@]2([C@@H]1O2)C)OC(=O)C)/C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3597521
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001550] Sesquiterpenoids

*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
NPO32699	parasenecio rubescens	Species	Asteraceae	Eukaryota	Whole Plant	n.a.	n.a.	PMID[26200396]

☑ 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	2

Activity Type	# Activity
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	IZ	=	8.0	mm	PMID[469079]
NPT19	Organism	Escherichia coli	Escherichia coli	IZ	=	8.0	mm	PMID[469079]

☑ 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 NPC472998 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	190
0.1-0.2	1439
0.2-0.3	4742
0.3-0.4	8918
0.4-0.5	13817
0.5-0.6	7964
0.6-0.7	4645
0.7-0.8	956
0.8-0.85	13
0.85-0.9	4
0.9-0.95	5
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9778	High Similarity	NPC469583
0.967	High Similarity	NPC472997
0.967	High Similarity	NPC472996
0.9247	High Similarity	NPC472995
0.8587	High Similarity	NPC475087
0.84	Intermediate Similarity	NPC472552
0.84	Intermediate Similarity	NPC470972
0.8384	Intermediate Similarity	NPC272223
0.835	Intermediate Similarity	NPC181994
0.8333	Intermediate Similarity	NPC470980
0.8302	Intermediate Similarity	NPC477126
0.83	Intermediate Similarity	NPC472554
0.8229	Intermediate Similarity	NPC122057
0.8229	Intermediate Similarity	NPC91251
0.8218	Intermediate Similarity	NPC109195
0.8218	Intermediate Similarity	NPC475038
0.8137	Intermediate Similarity	NPC61442
0.8125	Intermediate Similarity	NPC177668
0.8095	Intermediate Similarity	NPC475586
0.8021	Intermediate Similarity	NPC133450
0.8021	Intermediate Similarity	NPC161560
0.802	Intermediate Similarity	NPC188968
0.802	Intermediate Similarity	NPC79303
0.802	Intermediate Similarity	NPC38855
0.8	Intermediate Similarity	NPC199099
0.7961	Intermediate Similarity	NPC23584
0.7941	Intermediate Similarity	NPC11974
0.7938	Intermediate Similarity	NPC471378
0.7938	Intermediate Similarity	NPC312471
0.7938	Intermediate Similarity	NPC3952
0.7917	Intermediate Similarity	NPC75443
0.7917	Intermediate Similarity	NPC470260
0.7905	Intermediate Similarity	NPC471205
0.7905	Intermediate Similarity	NPC474716
0.7905	Intermediate Similarity	NPC469558
0.79	Intermediate Similarity	NPC476315
0.79	Intermediate Similarity	NPC279621
0.79	Intermediate Similarity	NPC475380
0.79	Intermediate Similarity	NPC209297
0.7879	Intermediate Similarity	NPC256368
0.7864	Intermediate Similarity	NPC11956
0.7857	Intermediate Similarity	NPC41838
0.7857	Intermediate Similarity	NPC158061
0.785	Intermediate Similarity	NPC177047
0.7843	Intermediate Similarity	NPC47024
0.7843	Intermediate Similarity	NPC271295
0.7838	Intermediate Similarity	NPC124676
0.7838	Intermediate Similarity	NPC146280
0.7835	Intermediate Similarity	NPC291875
0.783	Intermediate Similarity	NPC38948
0.783	Intermediate Similarity	NPC475263
0.783	Intermediate Similarity	NPC94377
0.7822	Intermediate Similarity	NPC120446
0.7822	Intermediate Similarity	NPC205143
0.7822	Intermediate Similarity	NPC311241
0.7822	Intermediate Similarity	NPC475446
0.7818	Intermediate Similarity	NPC471127
0.7818	Intermediate Similarity	NPC154363
0.7818	Intermediate Similarity	NPC234858
0.7812	Intermediate Similarity	NPC44538
0.781	Intermediate Similarity	NPC51719
0.7807	Intermediate Similarity	NPC473802
0.78	Intermediate Similarity	NPC14961
0.78	Intermediate Similarity	NPC36954
0.78	Intermediate Similarity	NPC270013
0.78	Intermediate Similarity	NPC476720
0.78	Intermediate Similarity	NPC276110
0.7789	Intermediate Similarity	NPC298595
0.7788	Intermediate Similarity	NPC474822
0.7778	Intermediate Similarity	NPC212486
0.7778	Intermediate Similarity	NPC476300
0.7778	Intermediate Similarity	NPC470076
0.7778	Intermediate Similarity	NPC469656
0.7778	Intermediate Similarity	NPC474846
0.7778	Intermediate Similarity	NPC469655
0.7768	Intermediate Similarity	NPC472667
0.7757	Intermediate Similarity	NPC206618
0.7748	Intermediate Similarity	NPC296822
0.7748	Intermediate Similarity	NPC10721
0.7745	Intermediate Similarity	NPC72647
0.7745	Intermediate Similarity	NPC107806
0.7745	Intermediate Similarity	NPC475068
0.7745	Intermediate Similarity	NPC474213
0.7739	Intermediate Similarity	NPC473919
0.7739	Intermediate Similarity	NPC473709
0.7736	Intermediate Similarity	NPC122816
0.7736	Intermediate Similarity	NPC187435
0.7736	Intermediate Similarity	NPC473586
0.7736	Intermediate Similarity	NPC67321
0.7732	Intermediate Similarity	NPC92370
0.7727	Intermediate Similarity	NPC216665
0.7727	Intermediate Similarity	NPC73314
0.7727	Intermediate Similarity	NPC472400
0.7719	Intermediate Similarity	NPC162009
0.7719	Intermediate Similarity	NPC257017
0.7714	Intermediate Similarity	NPC283850
0.7714	Intermediate Similarity	NPC477127
0.7708	Intermediate Similarity	NPC475684
0.7706	Intermediate Similarity	NPC328074
0.7706	Intermediate Similarity	NPC321272
0.7706	Intermediate Similarity	NPC317460
0.7706	Intermediate Similarity	NPC470025
0.7706	Intermediate Similarity	NPC473877
0.77	Intermediate Similarity	NPC161998
0.77	Intermediate Similarity	NPC81386
0.77	Intermediate Similarity	NPC140277
0.77	Intermediate Similarity	NPC105490
0.77	Intermediate Similarity	NPC474035
0.77	Intermediate Similarity	NPC474247
0.7699	Intermediate Similarity	NPC475885
0.7699	Intermediate Similarity	NPC157252
0.7699	Intermediate Similarity	NPC471126
0.7699	Intermediate Similarity	NPC145182
0.7699	Intermediate Similarity	NPC143755
0.7699	Intermediate Similarity	NPC471128
0.7685	Intermediate Similarity	NPC316708
0.7677	Intermediate Similarity	NPC30515
0.7677	Intermediate Similarity	NPC312805
0.7677	Intermediate Similarity	NPC184463
0.7672	Intermediate Similarity	NPC471939
0.767	Intermediate Similarity	NPC16601
0.7667	Intermediate Similarity	NPC477306
0.7664	Intermediate Similarity	NPC50124
0.7664	Intermediate Similarity	NPC128795
0.7664	Intermediate Similarity	NPC469916
0.7664	Intermediate Similarity	NPC217921
0.7664	Intermediate Similarity	NPC48548
0.7664	Intermediate Similarity	NPC472439
0.7664	Intermediate Similarity	NPC135015
0.7658	Intermediate Similarity	NPC474333
0.7658	Intermediate Similarity	NPC470075
0.7658	Intermediate Similarity	NPC471816
0.7652	Intermediate Similarity	NPC469352
0.7647	Intermediate Similarity	NPC100912
0.7647	Intermediate Similarity	NPC473963
0.7647	Intermediate Similarity	NPC136781
0.7647	Intermediate Similarity	NPC473244
0.7642	Intermediate Similarity	NPC471206
0.7642	Intermediate Similarity	NPC88349
0.7642	Intermediate Similarity	NPC239961
0.7636	Intermediate Similarity	NPC470027
0.7636	Intermediate Similarity	NPC472757
0.7632	Intermediate Similarity	NPC52839
0.7627	Intermediate Similarity	NPC475371
0.7624	Intermediate Similarity	NPC471141
0.7619	Intermediate Similarity	NPC474124
0.7619	Intermediate Similarity	NPC72842
0.7619	Intermediate Similarity	NPC471938
0.7619	Intermediate Similarity	NPC474575
0.7619	Intermediate Similarity	NPC99510
0.7619	Intermediate Similarity	NPC281378
0.7615	Intermediate Similarity	NPC470026
0.7615	Intermediate Similarity	NPC17791
0.7611	Intermediate Similarity	NPC236918
0.7611	Intermediate Similarity	NPC470186
0.7611	Intermediate Similarity	NPC156745
0.7609	Intermediate Similarity	NPC477314
0.7607	Intermediate Similarity	NPC471940
0.7604	Intermediate Similarity	NPC149725
0.7604	Intermediate Similarity	NPC471379
0.7604	Intermediate Similarity	NPC47958
0.7604	Intermediate Similarity	NPC196911
0.7604	Intermediate Similarity	NPC304509
0.76	Intermediate Similarity	NPC110022
0.76	Intermediate Similarity	NPC7349
0.76	Intermediate Similarity	NPC472196
0.76	Intermediate Similarity	NPC228451
0.76	Intermediate Similarity	NPC472195
0.76	Intermediate Similarity	NPC238090
0.76	Intermediate Similarity	NPC475838
0.76	Intermediate Similarity	NPC475912
0.76	Intermediate Similarity	NPC125674
0.7596	Intermediate Similarity	NPC98225
0.7596	Intermediate Similarity	NPC475617
0.7596	Intermediate Similarity	NPC308824
0.7596	Intermediate Similarity	NPC475958
0.7593	Intermediate Similarity	NPC299590
0.7593	Intermediate Similarity	NPC40728
0.7593	Intermediate Similarity	NPC316974
0.7593	Intermediate Similarity	NPC42662
0.7589	Intermediate Similarity	NPC469684
0.7589	Intermediate Similarity	NPC13713
0.7589	Intermediate Similarity	NPC53396
0.7589	Intermediate Similarity	NPC58662
0.7589	Intermediate Similarity	NPC473968
0.7589	Intermediate Similarity	NPC98249
0.7579	Intermediate Similarity	NPC231601
0.7579	Intermediate Similarity	NPC127917
0.7576	Intermediate Similarity	NPC475748
0.7576	Intermediate Similarity	NPC474761
0.7576	Intermediate Similarity	NPC476004
0.7576	Intermediate Similarity	NPC51004
0.7573	Intermediate Similarity	NPC222303
0.7573	Intermediate Similarity	NPC473326
0.757	Intermediate Similarity	NPC125423
0.757	Intermediate Similarity	NPC88013
0.7568	Intermediate Similarity	NPC43213
0.7556	Intermediate Similarity	NPC477305
0.7556	Intermediate Similarity	NPC477313
0.7556	Intermediate Similarity	NPC477316

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 NPC472998 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	162
0.1-0.2	1886
0.2-0.3	3826
0.3-0.4	2241
0.4-0.5	690
0.5-0.6	274
0.6-0.7	62
0.7-0.8	8
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
0.8673	High Similarity	NPD5344	Discontinued
0.82	Intermediate Similarity	NPD6648	Approved
0.8125	Intermediate Similarity	NPD7838	Discovery
0.7938	Intermediate Similarity	NPD46	Approved
0.7938	Intermediate Similarity	NPD6698	Approved
0.7593	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7404	Intermediate Similarity	NPD4225	Approved
0.7364	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7304	Intermediate Similarity	NPD7516	Approved
0.7217	Intermediate Similarity	NPD7327	Approved
0.7217	Intermediate Similarity	NPD7328	Approved
0.7091	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.7075	Intermediate Similarity	NPD7638	Approved
0.7075	Intermediate Similarity	NPD8029	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD6686	Approved
0.7009	Intermediate Similarity	NPD7640	Approved
0.7009	Intermediate Similarity	NPD7639	Approved
0.6983	Remote Similarity	NPD7115	Discovery
0.6903	Remote Similarity	NPD6371	Approved
0.6891	Remote Similarity	NPD8379	Approved
0.6891	Remote Similarity	NPD8296	Approved
0.6891	Remote Similarity	NPD8033	Approved
0.6891	Remote Similarity	NPD8335	Approved
0.6891	Remote Similarity	NPD8378	Approved
0.6891	Remote Similarity	NPD8380	Approved
0.6875	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6807	Remote Similarity	NPD8377	Approved
0.6807	Remote Similarity	NPD8294	Approved
0.675	Remote Similarity	NPD7503	Approved
0.6733	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6731	Remote Similarity	NPD3168	Discontinued
0.6696	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7532	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7983	Approved
0.6667	Remote Similarity	NPD7507	Approved
0.664	Remote Similarity	NPD7319	Approved
0.6612	Remote Similarity	NPD8515	Approved
0.6612	Remote Similarity	NPD8516	Approved
0.6612	Remote Similarity	NPD8517	Approved
0.6612	Remote Similarity	NPD8513	Phase 3
0.6476	Remote Similarity	NPD1695	Approved
0.6442	Remote Similarity	NPD7524	Approved
0.6441	Remote Similarity	NPD8133	Approved
0.6429	Remote Similarity	NPD3653	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD7632	Discontinued
0.6393	Remote Similarity	NPD6319	Approved
0.6356	Remote Similarity	NPD8297	Approved
0.6356	Remote Similarity	NPD6053	Discontinued
0.6349	Remote Similarity	NPD8074	Phase 3
0.6341	Remote Similarity	NPD6921	Approved
0.6304	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6303	Remote Similarity	NPD4632	Approved
0.6286	Remote Similarity	NPD4251	Approved
0.6286	Remote Similarity	NPD4250	Approved
0.6261	Remote Similarity	NPD6008	Approved
0.6261	Remote Similarity	NPD5357	Phase 1
0.625	Remote Similarity	NPD1694	Approved
0.6204	Remote Similarity	NPD7637	Suspended
0.619	Remote Similarity	NPD4249	Approved
0.619	Remote Similarity	NPD7492	Approved
0.6182	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD6881	Approved
0.6154	Remote Similarity	NPD6899	Approved
0.6147	Remote Similarity	NPD5779	Approved
0.6147	Remote Similarity	NPD5778	Approved
0.6142	Remote Similarity	NPD6616	Approved
0.6134	Remote Similarity	NPD6650	Approved
0.6134	Remote Similarity	NPD6649	Approved
0.6129	Remote Similarity	NPD6054	Approved
0.6121	Remote Similarity	NPD5739	Approved
0.6121	Remote Similarity	NPD7128	Approved
0.6121	Remote Similarity	NPD6402	Approved
0.6121	Remote Similarity	NPD6675	Approved
0.6111	Remote Similarity	NPD7642	Approved
0.6111	Remote Similarity	NPD7830	Approved
0.6111	Remote Similarity	NPD7604	Phase 2
0.6111	Remote Similarity	NPD7829	Approved
0.6102	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6102	Remote Similarity	NPD6372	Approved
0.6102	Remote Similarity	NPD6373	Approved
0.6095	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6094	Remote Similarity	NPD7078	Approved
0.6083	Remote Similarity	NPD6882	Approved
0.6078	Remote Similarity	NPD4821	Approved
0.6078	Remote Similarity	NPD4822	Approved
0.6078	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6078	Remote Similarity	NPD4820	Approved
0.6078	Remote Similarity	NPD4819	Approved
0.6068	Remote Similarity	NPD5697	Approved
0.6068	Remote Similarity	NPD6412	Phase 2
0.6058	Remote Similarity	NPD7154	Phase 3
0.6058	Remote Similarity	NPD6695	Phase 3
0.6053	Remote Similarity	NPD4159	Approved
0.605	Remote Similarity	NPD6883	Approved
0.605	Remote Similarity	NPD7290	Approved
0.605	Remote Similarity	NPD7102	Approved
0.6047	Remote Similarity	NPD7736	Approved
0.6032	Remote Similarity	NPD6370	Approved
0.6022	Remote Similarity	NPD371	Approved
0.6017	Remote Similarity	NPD7320	Approved
0.6016	Remote Similarity	NPD8273	Phase 1
0.6016	Remote Similarity	NPD6009	Approved
0.6	Remote Similarity	NPD6617	Approved
0.6	Remote Similarity	NPD6869	Approved
0.6	Remote Similarity	NPD6059	Approved
0.6	Remote Similarity	NPD6847	Approved
0.6	Remote Similarity	NPD8130	Phase 1
0.5984	Remote Similarity	NPD8328	Phase 3
0.5969	Remote Similarity	NPD8293	Discontinued
0.5966	Remote Similarity	NPD6013	Approved
0.5966	Remote Similarity	NPD6014	Approved
0.5966	Remote Similarity	NPD6012	Approved
0.5963	Remote Similarity	NPD5785	Approved
0.5962	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.5952	Remote Similarity	NPD5983	Phase 2
0.5952	Remote Similarity	NPD6016	Approved
0.5952	Remote Similarity	NPD6015	Approved
0.5946	Remote Similarity	NPD5282	Discontinued
0.5946	Remote Similarity	NPD7748	Approved
0.5932	Remote Similarity	NPD5701	Approved
0.5929	Remote Similarity	NPD7902	Approved
0.5926	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.5909	Remote Similarity	NPD7515	Phase 2
0.5906	Remote Similarity	NPD5988	Approved
0.5905	Remote Similarity	NPD6110	Phase 1
0.5891	Remote Similarity	NPD6336	Discontinued
0.5887	Remote Similarity	NPD7505	Discontinued
0.5882	Remote Similarity	NPD4268	Approved
0.5882	Remote Similarity	NPD4271	Approved
0.5882	Remote Similarity	NPD6011	Approved
0.5856	Remote Similarity	NPD6399	Phase 3
0.5845	Remote Similarity	NPD7274	Clinical (unspecified phase)
0.5841	Remote Similarity	NPD7839	Suspended
0.5841	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.5833	Remote Similarity	NPD7750	Discontinued
0.5794	Remote Similarity	NPD5363	Approved
0.5789	Remote Similarity	NPD7260	Phase 2
0.5789	Remote Similarity	NPD6083	Phase 2
0.5789	Remote Similarity	NPD6084	Phase 2
0.5785	Remote Similarity	NPD4634	Approved
0.5776	Remote Similarity	NPD1700	Approved
0.5769	Remote Similarity	NPD6930	Phase 2
0.5769	Remote Similarity	NPD7525	Registered
0.5769	Remote Similarity	NPD6931	Approved
0.5766	Remote Similarity	NPD8034	Phase 2
0.5766	Remote Similarity	NPD8035	Phase 2
0.576	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.5755	Remote Similarity	NPD5362	Discontinued
0.5738	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.5727	Remote Similarity	NPD6051	Approved
0.5727	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.5727	Remote Similarity	NPD6101	Approved
0.5726	Remote Similarity	NPD5211	Phase 2
0.5714	Remote Similarity	NPD7641	Discontinued
0.5699	Remote Similarity	NPD1145	Discontinued
0.569	Remote Similarity	NPD4696	Approved
0.569	Remote Similarity	NPD5285	Approved
0.569	Remote Similarity	NPD5286	Approved
0.568	Remote Similarity	NPD6274	Approved
0.5673	Remote Similarity	NPD6929	Approved
0.5669	Remote Similarity	NPD7100	Approved
0.5669	Remote Similarity	NPD7101	Approved
0.5664	Remote Similarity	NPD7625	Phase 1
0.5664	Remote Similarity	NPD7900	Approved
0.5664	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.566	Remote Similarity	NPD6435	Approved
0.566	Remote Similarity	NPD5209	Approved
0.5656	Remote Similarity	NPD6421	Discontinued
0.5652	Remote Similarity	NPD4755	Approved
0.5649	Remote Similarity	NPD8451	Approved
0.5648	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.563	Remote Similarity	NPD5141	Approved
0.563	Remote Similarity	NPD6845	Suspended
0.5625	Remote Similarity	NPD7087	Discontinued
0.5625	Remote Similarity	NPD6079	Approved
0.5625	Remote Similarity	NPD6411	Approved
0.562	Remote Similarity	NPD8387	Clinical (unspecified phase)
0.5619	Remote Similarity	NPD7332	Phase 2
0.5619	Remote Similarity	NPD7514	Phase 3
0.5615	Remote Similarity	NPD6067	Discontinued
0.5614	Remote Similarity	NPD5695	Phase 3
0.5614	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.5607	Remote Similarity	NPD5332	Approved
0.5607	Remote Similarity	NPD5331	Approved
0.5606	Remote Similarity	NPD8448	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