NPASS Compound

Structure

NPC474822 OpenBabel07101718182D 24 28 0 0 1 0 0 0 0 0999 V2000 -0.3090 2.5691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 -0.6910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2812 0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4152 -1.6910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4152 1.3090 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 3.5491 1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 -0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1472 -0.6910 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 5.2812 -1.1910 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.9511 0.3090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.4152 0.3090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.6831 0.3090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.9511 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 1.8090 0.0000 C 0 0 2 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 3.5491 -0.1910 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.2812 -0.1910 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.6831 1.3090 0.0000 C 0 0 2 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 -1.5878 0.8090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 2.3090 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 10 1 0 0 0 0 4 6 1 0 0 0 0 4 11 1 0 0 0 0 5 7 1 0 0 0 0 5 13 1 0 0 0 0 6 18 1 0 0 0 0 7 20 1 0 0 0 0 8 14 1 0 0 0 0 9 11 1 0 0 0 0 9 19 1 0 0 0 0 10 15 2 0 0 0 0 10 17 1 0 0 0 0 11 19 1 1 0 0 0 12 8 1 1 0 0 0 12 15 1 0 0 0 0 12 24 1 0 0 0 0 13 18 1 6 0 0 0 13 19 1 0 0 0 0 14 18 1 6 0 0 0 14 20 1 0 0 0 0 15 16 1 0 0 0 0 16 20 1 1 0 0 0 16 21 1 0 0 0 0 17 22 2 0 0 0 0 17 24 1 0 0 0 0 18 2 1 6 0 0 0 19 3 1 6 0 0 0 20 23 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	332.2
Volume:	341.582
LogP:	3.221
LogD:	3.148
LogS:	-3.512
# Rotatable Bonds:	0
TPSA:	73.83
# H-Bond Aceptor:	4
# H-Bond Donor:	3
# Rings:	5
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.68
Synthetic Accessibility Score:	5.078
Fsp3:	0.8
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.825
MDCK Permeability:	1.2902557500638068e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.896
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.057

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.844
Plasma Protein Binding (PPB):	95.3885269165039%
Volume Distribution (VD):	1.518
Pgp-substrate:	6.883402347564697%

ADMET: Metabolism

CYP1A2-inhibitor:	0.035
CYP1A2-substrate:	0.605
CYP2C19-inhibitor:	0.013
CYP2C19-substrate:	0.685
CYP2C9-inhibitor:	0.068
CYP2C9-substrate:	0.355
CYP2D6-inhibitor:	0.013
CYP2D6-substrate:	0.321
CYP3A4-inhibitor:	0.125
CYP3A4-substrate:	0.132

ADMET: Excretion

Clearance (CL):	8.506
Half-life (T1/2):	0.245

ADMET: Toxicity

hERG Blockers:	0.042
Human Hepatotoxicity (H-HT):	0.281
Drug-inuced Liver Injury (DILI):	0.233
AMES Toxicity:	0.011
Rat Oral Acute Toxicity:	0.64
Maximum Recommended Daily Dose:	0.876
Skin Sensitization:	0.381
Carcinogencity:	0.088
Eye Corrosion:	0.004
Eye Irritation:	0.063
Respiratory Toxicity:	0.975

Download Data

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

Natural Product: NPC474822

Natural Product ID:	NPC474822
*Common Name:**	Suregadolide A
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	ZZRMOWIKHWOSFN-LAFNOEKWSA-N
Standard InCHI:	InChI=1S/C20H28O4/c1-10-15-12(24-17(10)22)8-14-18(2)6-4-11-9-19(11,3)13(18)5-7-20(14,23)16(15)21/h11-14,16,21,23H,4-9H2,1-3H3/t11-,12-,13+,14+,16-,18-,19+,20+/m1/s1
SMILES:	O=C1O[C@H]2C(=C1C)[C@@H](O)[C@]1([C@@H](C2)[C@]2(C)CC[C@H]3[C@]([C@H]2CC1)(C)C3)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL484047
PubChem CID:	10471965
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001634] Naphthofurans

*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
NPO7787	Suregada multiflora	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12088443]
NPO7787	Suregada multiflora	Species	Euphorbiaceae	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
Others	2

Activity Type	# Activity
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT312	Organism	Saccharomyces cerevisiae	Saccharomyces cerevisiae	IC12	=	35.0	ug ml-1	PMID[491455]
NPT312	Organism	Saccharomyces cerevisiae	Saccharomyces cerevisiae	IC12	=	70.0	ug ml-1	PMID[491455]

☑ 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 NPC474822 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	246
0.1-0.2	1773
0.2-0.3	4782
0.3-0.4	8449
0.4-0.5	13157
0.5-0.6	7071
0.6-0.7	5611
0.7-0.8	1501
0.8-0.85	81
0.85-0.9	18
0.9-0.95	3
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
0.9053	High Similarity	NPC110022
0.875	High Similarity	NPC299590
0.8738	High Similarity	NPC471205
0.8738	High Similarity	NPC122816
0.87	High Similarity	NPC38855
0.8687	High Similarity	NPC199099
0.8679	High Similarity	NPC42658
0.8673	High Similarity	NPC471915
0.8673	High Similarity	NPC111273
0.866	High Similarity	NPC472640
0.866	High Similarity	NPC472641
0.8654	High Similarity	NPC181994
0.8627	High Similarity	NPC165608
0.8614	High Similarity	NPC11974
0.8557	High Similarity	NPC78594
0.8529	High Similarity	NPC475038
0.8529	High Similarity	NPC109195
0.8529	High Similarity	NPC472552
0.8515	High Similarity	NPC16601
0.8491	Intermediate Similarity	NPC177047
0.8485	Intermediate Similarity	NPC276110
0.8476	Intermediate Similarity	NPC50124
0.8462	Intermediate Similarity	NPC477090
0.8462	Intermediate Similarity	NPC51719
0.8454	Intermediate Similarity	NPC472642
0.8431	Intermediate Similarity	NPC472554
0.8416	Intermediate Similarity	NPC275086
0.8416	Intermediate Similarity	NPC325229
0.8384	Intermediate Similarity	NPC105490
0.8381	Intermediate Similarity	NPC187435
0.8381	Intermediate Similarity	NPC67321
0.835	Intermediate Similarity	NPC165250
0.835	Intermediate Similarity	NPC295791
0.835	Intermediate Similarity	NPC471914
0.8333	Intermediate Similarity	NPC79303
0.8333	Intermediate Similarity	NPC188968
0.8317	Intermediate Similarity	NPC51499
0.8302	Intermediate Similarity	NPC38948
0.8286	Intermediate Similarity	NPC81630
0.8286	Intermediate Similarity	NPC471206
0.8283	Intermediate Similarity	NPC7349
0.8269	Intermediate Similarity	NPC471938
0.8269	Intermediate Similarity	NPC281378
0.8269	Intermediate Similarity	NPC472821
0.8269	Intermediate Similarity	NPC159533
0.8269	Intermediate Similarity	NPC23584
0.8269	Intermediate Similarity	NPC45897
0.8241	Intermediate Similarity	NPC469655
0.8241	Intermediate Similarity	NPC470076
0.8241	Intermediate Similarity	NPC474846
0.8241	Intermediate Similarity	NPC469656
0.8224	Intermediate Similarity	NPC206618
0.8218	Intermediate Similarity	NPC165632
0.8211	Intermediate Similarity	NPC32223
0.8208	Intermediate Similarity	NPC473586
0.819	Intermediate Similarity	NPC161775
0.819	Intermediate Similarity	NPC471937
0.8173	Intermediate Similarity	NPC11956
0.8173	Intermediate Similarity	NPC476081
0.8165	Intermediate Similarity	NPC472002
0.8155	Intermediate Similarity	NPC271295
0.8155	Intermediate Similarity	NPC324841
0.8142	Intermediate Similarity	NPC154491
0.8142	Intermediate Similarity	NPC268530
0.8137	Intermediate Similarity	NPC205143
0.8131	Intermediate Similarity	NPC475263
0.8131	Intermediate Similarity	NPC325054
0.8131	Intermediate Similarity	NPC306265
0.8131	Intermediate Similarity	NPC88701
0.8119	Intermediate Similarity	NPC329435
0.8113	Intermediate Similarity	NPC88349
0.8113	Intermediate Similarity	NPC119855
0.8113	Intermediate Similarity	NPC220217
0.8113	Intermediate Similarity	NPC186668
0.8108	Intermediate Similarity	NPC470075
0.81	Intermediate Similarity	NPC53555
0.8095	Intermediate Similarity	NPC97487
0.8095	Intermediate Similarity	NPC189588
0.8095	Intermediate Similarity	NPC196471
0.8095	Intermediate Similarity	NPC160583
0.8095	Intermediate Similarity	NPC471208
0.8095	Intermediate Similarity	NPC10232
0.8095	Intermediate Similarity	NPC187302
0.8081	Intermediate Similarity	NPC78973
0.8077	Intermediate Similarity	NPC475617
0.807	Intermediate Similarity	NPC4021
0.807	Intermediate Similarity	NPC159456
0.8058	Intermediate Similarity	NPC278673
0.8058	Intermediate Similarity	NPC218107
0.8056	Intermediate Similarity	NPC31522
0.8056	Intermediate Similarity	NPC475586
0.8039	Intermediate Similarity	NPC129569
0.8039	Intermediate Similarity	NPC209297
0.8039	Intermediate Similarity	NPC473153
0.8039	Intermediate Similarity	NPC194132
0.8039	Intermediate Similarity	NPC472995
0.8039	Intermediate Similarity	NPC475380
0.8036	Intermediate Similarity	NPC13713
0.8036	Intermediate Similarity	NPC58662
0.8036	Intermediate Similarity	NPC55296
0.802	Intermediate Similarity	NPC140277
0.8019	Intermediate Similarity	NPC473543
0.8	Intermediate Similarity	NPC470063
0.8	Intermediate Similarity	NPC472815
0.8	Intermediate Similarity	NPC273668
0.8	Intermediate Similarity	NPC165578
0.8	Intermediate Similarity	NPC121423
0.7982	Intermediate Similarity	NPC251226
0.7981	Intermediate Similarity	NPC251680
0.7981	Intermediate Similarity	NPC474190
0.7965	Intermediate Similarity	NPC240509
0.7963	Intermediate Similarity	NPC90946
0.7963	Intermediate Similarity	NPC300614
0.7963	Intermediate Similarity	NPC472439
0.7963	Intermediate Similarity	NPC469916
0.7961	Intermediate Similarity	NPC224356
0.7961	Intermediate Similarity	NPC132753
0.7961	Intermediate Similarity	NPC120446
0.7961	Intermediate Similarity	NPC175351
0.7961	Intermediate Similarity	NPC473244
0.7961	Intermediate Similarity	NPC100912
0.7961	Intermediate Similarity	NPC311241
0.7961	Intermediate Similarity	NPC151681
0.7961	Intermediate Similarity	NPC121402
0.7961	Intermediate Similarity	NPC254121
0.7961	Intermediate Similarity	NPC475446
0.7959	Intermediate Similarity	NPC473891
0.7946	Intermediate Similarity	NPC154363
0.7946	Intermediate Similarity	NPC471816
0.7946	Intermediate Similarity	NPC234858
0.7946	Intermediate Similarity	NPC471127
0.7946	Intermediate Similarity	NPC179626
0.7944	Intermediate Similarity	NPC472818
0.7938	Intermediate Similarity	NPC253604
0.7925	Intermediate Similarity	NPC99510
0.7925	Intermediate Similarity	NPC474124
0.7925	Intermediate Similarity	NPC61442
0.7925	Intermediate Similarity	NPC72842
0.7925	Intermediate Similarity	NPC120009
0.7925	Intermediate Similarity	NPC473523
0.7925	Intermediate Similarity	NPC120321
0.7905	Intermediate Similarity	NPC268829
0.7905	Intermediate Similarity	NPC235920
0.7905	Intermediate Similarity	NPC25177
0.7905	Intermediate Similarity	NPC247701
0.7905	Intermediate Similarity	NPC222875
0.7905	Intermediate Similarity	NPC295110
0.7905	Intermediate Similarity	NPC289670
0.7905	Intermediate Similarity	NPC96784
0.7895	Intermediate Similarity	NPC230513
0.789	Intermediate Similarity	NPC257853
0.789	Intermediate Similarity	NPC322912
0.7885	Intermediate Similarity	NPC107806
0.7885	Intermediate Similarity	NPC222303
0.7885	Intermediate Similarity	NPC102426
0.7885	Intermediate Similarity	NPC300179
0.7885	Intermediate Similarity	NPC72647
0.7879	Intermediate Similarity	NPC242448
0.7876	Intermediate Similarity	NPC469684
0.7876	Intermediate Similarity	NPC10721
0.787	Intermediate Similarity	NPC473173
0.787	Intermediate Similarity	NPC471783
0.787	Intermediate Similarity	NPC472820
0.787	Intermediate Similarity	NPC9457
0.787	Intermediate Similarity	NPC469318
0.787	Intermediate Similarity	NPC180744
0.7864	Intermediate Similarity	NPC72204
0.7864	Intermediate Similarity	NPC234993
0.7864	Intermediate Similarity	NPC472362
0.7864	Intermediate Similarity	NPC472363
0.7864	Intermediate Similarity	NPC471903
0.7864	Intermediate Similarity	NPC284194
0.7864	Intermediate Similarity	NPC211810
0.7864	Intermediate Similarity	NPC221801
0.7864	Intermediate Similarity	NPC471765
0.7864	Intermediate Similarity	NPC260796
0.7864	Intermediate Similarity	NPC134072
0.7864	Intermediate Similarity	NPC154526
0.7857	Intermediate Similarity	NPC131813
0.7857	Intermediate Similarity	NPC472400
0.785	Intermediate Similarity	NPC472819
0.785	Intermediate Similarity	NPC283850
0.7843	Intermediate Similarity	NPC182826
0.7843	Intermediate Similarity	NPC105375
0.7843	Intermediate Similarity	NPC161998
0.7843	Intermediate Similarity	NPC57117
0.7838	Intermediate Similarity	NPC269530
0.783	Intermediate Similarity	NPC162973
0.783	Intermediate Similarity	NPC469316
0.783	Intermediate Similarity	NPC475344
0.783	Intermediate Similarity	NPC283343
0.783	Intermediate Similarity	NPC258547
0.783	Intermediate Similarity	NPC476471
0.7826	Intermediate Similarity	NPC475885
0.7822	Intermediate Similarity	NPC41239
0.7822	Intermediate Similarity	NPC124374
0.7822	Intermediate Similarity	NPC114389
0.7822	Intermediate Similarity	NPC219516
0.7822	Intermediate Similarity	NPC329842
0.7818	Intermediate Similarity	NPC472215

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 NPC474822 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	216
0.1-0.2	1987
0.2-0.3	3819
0.3-0.4	2077
0.4-0.5	654
0.5-0.6	280
0.6-0.7	92
0.7-0.8	23
0.8-0.85	1
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.875	High Similarity	NPD4061	Clinical (unspecified phase)
0.8318	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.8037	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.7981	Intermediate Similarity	NPD7639	Approved
0.7981	Intermediate Similarity	NPD7640	Approved
0.7905	Intermediate Similarity	NPD5344	Discontinued
0.7895	Intermediate Similarity	NPD7516	Approved
0.7885	Intermediate Similarity	NPD7638	Approved
0.783	Intermediate Similarity	NPD7632	Discontinued
0.7807	Intermediate Similarity	NPD7328	Approved
0.7807	Intermediate Similarity	NPD7327	Approved
0.7714	Intermediate Similarity	NPD4225	Approved
0.7477	Intermediate Similarity	NPD6648	Approved
0.7458	Intermediate Similarity	NPD8296	Approved
0.7458	Intermediate Similarity	NPD8033	Approved
0.7458	Intermediate Similarity	NPD8378	Approved
0.7458	Intermediate Similarity	NPD8335	Approved
0.7458	Intermediate Similarity	NPD8379	Approved
0.7458	Intermediate Similarity	NPD8380	Approved
0.7373	Intermediate Similarity	NPD8294	Approved
0.7373	Intermediate Similarity	NPD8377	Approved
0.7321	Intermediate Similarity	NPD6686	Approved
0.7265	Intermediate Similarity	NPD7115	Discovery
0.7213	Intermediate Similarity	NPD7507	Approved
0.7177	Intermediate Similarity	NPD7319	Approved
0.7168	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.6937	Remote Similarity	NPD4159	Approved
0.6885	Remote Similarity	NPD7503	Approved
0.681	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6762	Remote Similarity	NPD7524	Approved
0.6752	Remote Similarity	NPD6371	Approved
0.6729	Remote Similarity	NPD6698	Approved
0.6729	Remote Similarity	NPD7838	Discovery
0.6729	Remote Similarity	NPD46	Approved
0.6723	Remote Similarity	NPD4632	Approved
0.6723	Remote Similarity	NPD8133	Approved
0.6697	Remote Similarity	NPD7748	Approved
0.6696	Remote Similarity	NPD6675	Approved
0.6696	Remote Similarity	NPD6008	Approved
0.6696	Remote Similarity	NPD7128	Approved
0.6696	Remote Similarity	NPD6402	Approved
0.6696	Remote Similarity	NPD5739	Approved
0.6667	Remote Similarity	NPD7902	Approved
0.6667	Remote Similarity	NPD6319	Approved
0.6667	Remote Similarity	NPD7637	Suspended
0.6667	Remote Similarity	NPD7515	Phase 2
0.6638	Remote Similarity	NPD5701	Approved
0.6638	Remote Similarity	NPD5697	Approved
0.6635	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6602	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6581	Remote Similarity	NPD7320	Approved
0.6581	Remote Similarity	NPD6899	Approved
0.6581	Remote Similarity	NPD6881	Approved
0.6569	Remote Similarity	NPD7525	Registered
0.6557	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6538	Remote Similarity	NPD6695	Phase 3
0.6525	Remote Similarity	NPD6012	Approved
0.6525	Remote Similarity	NPD6373	Approved
0.6525	Remote Similarity	NPD6013	Approved
0.6525	Remote Similarity	NPD6372	Approved
0.6525	Remote Similarity	NPD6014	Approved
0.6508	Remote Similarity	NPD7604	Phase 2
0.65	Remote Similarity	NPD8297	Approved
0.65	Remote Similarity	NPD6053	Discontinued
0.6496	Remote Similarity	NPD6412	Phase 2
0.648	Remote Similarity	NPD6921	Approved
0.6476	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD7290	Approved
0.6471	Remote Similarity	NPD7102	Approved
0.6471	Remote Similarity	NPD6883	Approved
0.6455	Remote Similarity	NPD6399	Phase 3
0.6441	Remote Similarity	NPD6011	Approved
0.6435	Remote Similarity	NPD5211	Phase 2
0.6423	Remote Similarity	NPD6009	Approved
0.6417	Remote Similarity	NPD6847	Approved
0.6417	Remote Similarity	NPD6617	Approved
0.6417	Remote Similarity	NPD8130	Phase 1
0.6417	Remote Similarity	NPD6869	Approved
0.6417	Remote Similarity	NPD6649	Approved
0.6417	Remote Similarity	NPD6650	Approved
0.6396	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6396	Remote Similarity	NPD7900	Approved
0.6378	Remote Similarity	NPD8328	Phase 3
0.6372	Remote Similarity	NPD4755	Approved
0.6372	Remote Similarity	NPD6083	Phase 2
0.6372	Remote Similarity	NPD6084	Phase 2
0.6364	Remote Similarity	NPD8034	Phase 2
0.6364	Remote Similarity	NPD6882	Approved
0.6364	Remote Similarity	NPD8035	Phase 2
0.6355	Remote Similarity	NPD3618	Phase 1
0.6349	Remote Similarity	NPD5983	Phase 2
0.6333	Remote Similarity	NPD4634	Approved
0.633	Remote Similarity	NPD6051	Approved
0.6328	Remote Similarity	NPD7492	Approved
0.6325	Remote Similarity	NPD5141	Approved
0.6316	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6311	Remote Similarity	NPD7645	Phase 2
0.6308	Remote Similarity	NPD7736	Approved
0.6306	Remote Similarity	NPD4202	Approved
0.6296	Remote Similarity	NPD7750	Discontinued
0.6296	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6281	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6279	Remote Similarity	NPD6616	Approved
0.6273	Remote Similarity	NPD3168	Discontinued
0.627	Remote Similarity	NPD6054	Approved
0.627	Remote Similarity	NPD6059	Approved
0.6262	Remote Similarity	NPD1694	Approved
0.6262	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6261	Remote Similarity	NPD5286	Approved
0.6261	Remote Similarity	NPD5285	Approved
0.6261	Remote Similarity	NPD4700	Approved
0.6261	Remote Similarity	NPD4696	Approved
0.625	Remote Similarity	NPD6931	Approved
0.625	Remote Similarity	NPD6930	Phase 2
0.6231	Remote Similarity	NPD8293	Discontinued
0.6231	Remote Similarity	NPD7078	Approved
0.622	Remote Similarity	NPD8513	Phase 3
0.622	Remote Similarity	NPD6016	Approved
0.622	Remote Similarity	NPD8515	Approved
0.622	Remote Similarity	NPD8516	Approved
0.622	Remote Similarity	NPD6015	Approved
0.622	Remote Similarity	NPD8517	Approved
0.6214	Remote Similarity	NPD6118	Approved
0.6214	Remote Similarity	NPD6114	Approved
0.6214	Remote Similarity	NPD6697	Approved
0.6214	Remote Similarity	NPD6115	Approved
0.621	Remote Similarity	NPD6274	Approved
0.6195	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6195	Remote Similarity	NPD5695	Phase 3
0.619	Remote Similarity	NPD6902	Approved
0.6182	Remote Similarity	NPD5328	Approved
0.6174	Remote Similarity	NPD5696	Approved
0.6172	Remote Similarity	NPD6370	Approved
0.6172	Remote Similarity	NPD5988	Approved
0.6161	Remote Similarity	NPD5779	Approved
0.6161	Remote Similarity	NPD5778	Approved
0.6154	Remote Similarity	NPD5225	Approved
0.6154	Remote Similarity	NPD5226	Approved
0.6154	Remote Similarity	NPD5224	Approved
0.6154	Remote Similarity	NPD4633	Approved
0.6154	Remote Similarity	NPD6929	Approved
0.6154	Remote Similarity	NPD6336	Discontinued
0.6148	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6132	Remote Similarity	NPD3667	Approved
0.6127	Remote Similarity	NPD7625	Phase 1
0.6117	Remote Similarity	NPD6116	Phase 1
0.6111	Remote Similarity	NPD1696	Phase 3
0.6102	Remote Similarity	NPD5175	Approved
0.6102	Remote Similarity	NPD5174	Approved
0.6095	Remote Similarity	NPD7332	Phase 2
0.6095	Remote Similarity	NPD7514	Phase 3
0.6091	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6083	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6071	Remote Similarity	NPD5693	Phase 1
0.6071	Remote Similarity	NPD7087	Discontinued
0.6071	Remote Similarity	NPD6079	Approved
0.6068	Remote Similarity	NPD5223	Approved
0.6063	Remote Similarity	NPD7100	Approved
0.6063	Remote Similarity	NPD7101	Approved
0.6061	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.6055	Remote Similarity	NPD7146	Approved
0.6055	Remote Similarity	NPD7334	Approved
0.6055	Remote Similarity	NPD6409	Approved
0.6055	Remote Similarity	NPD5330	Approved
0.6055	Remote Similarity	NPD6684	Approved
0.6055	Remote Similarity	NPD7521	Approved
0.6036	Remote Similarity	NPD4753	Phase 2
0.6032	Remote Similarity	NPD6317	Approved
0.6019	Remote Similarity	NPD6117	Approved
0.6019	Remote Similarity	NPD4786	Approved
0.6019	Remote Similarity	NPD3133	Approved
0.6019	Remote Similarity	NPD3666	Approved
0.6019	Remote Similarity	NPD3665	Phase 1
0.6019	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6017	Remote Similarity	NPD3653	Clinical (unspecified phase)
0.6	Remote Similarity	NPD4767	Approved
0.6	Remote Similarity	NPD5222	Approved
0.6	Remote Similarity	NPD4768	Approved
0.6	Remote Similarity	NPD4697	Phase 3
0.6	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6	Remote Similarity	NPD3573	Approved
0.6	Remote Similarity	NPD5221	Approved
0.5985	Remote Similarity	NPD8074	Phase 3
0.5984	Remote Similarity	NPD6314	Approved
0.5984	Remote Similarity	NPD6313	Approved
0.5984	Remote Similarity	NPD6335	Approved
0.5972	Remote Similarity	NPD7274	Clinical (unspecified phase)
0.5969	Remote Similarity	NPD6909	Approved
0.5969	Remote Similarity	NPD6908	Approved
0.5966	Remote Similarity	NPD4754	Approved
0.5965	Remote Similarity	NPD6001	Approved
0.5963	Remote Similarity	NPD6893	Approved
0.5962	Remote Similarity	NPD5776	Phase 2
0.5962	Remote Similarity	NPD6925	Approved
0.5948	Remote Similarity	NPD5173	Approved
0.5946	Remote Similarity	NPD6672	Approved
0.5946	Remote Similarity	NPD5737	Approved
0.5946	Remote Similarity	NPD6903	Approved
0.5943	Remote Similarity	NPD4748	Discontinued
0.5929	Remote Similarity	NPD6411	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