NPASS Compound

Structure

NPC471112 OpenBabel07101719252D 34 40 0 0 1 0 0 0 0 0999 V2000 2.4232 -0.6901 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7187 0.8922 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5600 -2.8838 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2941 3.0138 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.2941 3.0138 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7367 -1.7658 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7367 1.0613 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0620 2.1478 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1960 1.6478 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.6601 0.6478 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7941 0.1478 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1960 -1.3522 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0620 -0.8522 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0223 -2.1793 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9281 -0.3522 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6142 -0.1023 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9722 -2.0748 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.6101 -1.3703 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.9281 1.6478 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.1960 0.6478 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.6601 1.6478 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.7006 -0.5090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.3789 -1.1613 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.3789 0.4568 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.7941 2.1478 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3300 -0.8522 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.3300 0.1478 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.9281 0.6478 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.0620 0.1478 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.7912 -0.3522 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.5261 2.1478 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0699 1.4078 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.2034 -0.4568 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 16 2 0 0 0 0 2 16 1 0 0 0 0 4 25 1 0 0 0 0 5 25 1 0 0 0 0 6 26 1 0 0 0 0 8 9 1 0 0 0 0 8 19 1 0 0 0 0 9 20 1 0 0 0 0 10 11 1 0 0 0 0 10 21 1 0 0 0 0 11 28 1 0 0 0 0 12 13 1 0 0 0 0 12 26 1 0 0 0 0 14 17 1 0 0 0 0 15 28 1 0 0 0 0 15 29 1 0 0 0 0 17 3 1 1 0 0 0 17 23 1 0 0 0 0 18 14 1 1 0 0 0 18 22 1 0 0 0 0 18 33 1 0 0 0 0 19 25 1 0 0 0 0 19 28 1 6 0 0 0 20 27 1 1 0 0 0 20 29 1 0 0 0 0 21 25 1 0 0 0 0 21 31 1 6 0 0 0 22 16 1 1 0 0 0 22 34 1 0 0 0 0 23 26 1 6 0 0 0 23 30 1 0 0 0 0 24 27 1 1 0 0 0 24 30 1 0 0 0 0 24 32 1 0 0 0 0 26 27 1 6 0 0 0 27 7 1 1 0 0 0 28 29 1 1 0 0 0 29 13 1 1 0 0 0 30 33 1 1 0 0 0 30 34 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	470.34
Volume:	500.065
LogP:	5.507
LogD:	4.53
LogS:	-4.608
# Rotatable Bonds:	1
TPSA:	58.92
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	7
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.5
Synthetic Accessibility Score:	7.023
Fsp3:	0.933
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-5.309
MDCK Permeability:	2.244940696982667e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.141
30% Bioavailability (F30%):	0.939

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.097
Plasma Protein Binding (PPB):	89.7568588256836%
Volume Distribution (VD):	1.698
Pgp-substrate:	5.464122772216797%

ADMET: Metabolism

CYP1A2-inhibitor:	0.009
CYP1A2-substrate:	0.767
CYP2C19-inhibitor:	0.032
CYP2C19-substrate:	0.859
CYP2C9-inhibitor:	0.191
CYP2C9-substrate:	0.034
CYP2D6-inhibitor:	0.007
CYP2D6-substrate:	0.563
CYP3A4-inhibitor:	0.691
CYP3A4-substrate:	0.356

ADMET: Excretion

Clearance (CL):	8.012
Half-life (T1/2):	0.31

ADMET: Toxicity

hERG Blockers:	0.756
Human Hepatotoxicity (H-HT):	0.97
Drug-inuced Liver Injury (DILI):	0.032
AMES Toxicity:	0.006
Rat Oral Acute Toxicity:	0.968
Maximum Recommended Daily Dose:	0.963
Skin Sensitization:	0.67
Carcinogencity:	0.021
Eye Corrosion:	0.008
Eye Irritation:	0.043
Respiratory Toxicity:	0.969

Download Data

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

Natural Product: NPC471112

Natural Product ID:	NPC471112
*Common Name:**	UNNXMCWXOOFOBL-HVVIKVJSSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	UNNXMCWXOOFOBL-HVVIKVJSSA-N
Standard InCHI:	InChI=1S/C30H46O4/c1-16(2)22-18-14-17(3)23-26(6)12-13-29-15-28(29)11-10-21(31)25(4,5)19(28)8-9-20(29)27(26,7)24(32)30(23,33-18)34-22/h17-24,31-32H,1,8-15H2,2-7H3/t17-,18-,19+,20+,21+,22+,23-,24-,26-,27-,28-,29+,30-/m1/s1
SMILES:	CC(=C)[C@@H]1O[C@@]23O[C@@H]1C[C@H]([C@@H]3[C@@]1([C@]([C@H]2O)(C)[C@@H]2CC[C@@H]3[C@@]4([C@@]2(CC1)C4)CC[C@@H](C3(C)C)O)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2375501
PubChem CID:	73350369
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0002321] Cycloartanols 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
NPO33019	cimicifuga yunnanensis	Species	Ranunculaceae	Eukaryota	aerial parts	n.a.	n.a.	PMID[23621813]

☑ 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
NPT1893	Cell Line	MEF	Mus musculus	IC50	=	6200.0	nM	PMID[574297]

☑ 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 NPC471112 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	292
0.1-0.2	2487
0.2-0.3	7705
0.3-0.4	14720
0.4-0.5	7275
0.5-0.6	5134
0.6-0.7	3858
0.7-0.8	1142
0.8-0.85	68
0.85-0.9	14
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.92	High Similarity	NPC476513
0.8889	High Similarity	NPC228049
0.8889	High Similarity	NPC68630
0.8889	High Similarity	NPC52585
0.8738	High Similarity	NPC128133
0.8713	High Similarity	NPC471111
0.8614	High Similarity	NPC475701
0.86	High Similarity	NPC31346
0.8558	High Similarity	NPC473570
0.8544	High Similarity	NPC54619
0.8529	High Similarity	NPC474464
0.8526	High Similarity	NPC228059
0.8515	High Similarity	NPC177701
0.85	High Similarity	NPC91497
0.85	High Similarity	NPC471247
0.8485	Intermediate Similarity	NPC76486
0.8469	Intermediate Similarity	NPC30477
0.8462	Intermediate Similarity	NPC125324
0.8462	Intermediate Similarity	NPC49032
0.8462	Intermediate Similarity	NPC51172
0.8447	Intermediate Similarity	NPC474015
0.8416	Intermediate Similarity	NPC176406
0.8396	Intermediate Similarity	NPC470311
0.8381	Intermediate Similarity	NPC151134
0.8302	Intermediate Similarity	NPC470867
0.8286	Intermediate Similarity	NPC473517
0.8286	Intermediate Similarity	NPC7213
0.8283	Intermediate Similarity	NPC473348
0.8269	Intermediate Similarity	NPC165405
0.8265	Intermediate Similarity	NPC296620
0.8235	Intermediate Similarity	NPC470168
0.8224	Intermediate Similarity	NPC13190
0.8218	Intermediate Similarity	NPC275865
0.8208	Intermediate Similarity	NPC472901
0.82	Intermediate Similarity	NPC472989
0.8173	Intermediate Similarity	NPC475521
0.8173	Intermediate Similarity	NPC475365
0.8155	Intermediate Similarity	NPC31085
0.8148	Intermediate Similarity	NPC112274
0.8119	Intermediate Similarity	NPC177818
0.8105	Intermediate Similarity	NPC273290
0.8105	Intermediate Similarity	NPC232044
0.81	Intermediate Similarity	NPC473067
0.81	Intermediate Similarity	NPC473065
0.81	Intermediate Similarity	NPC473064
0.8095	Intermediate Similarity	NPC26798
0.8081	Intermediate Similarity	NPC242419
0.8081	Intermediate Similarity	NPC307776
0.8081	Intermediate Similarity	NPC235126
0.8077	Intermediate Similarity	NPC473198
0.8077	Intermediate Similarity	NPC471467
0.8077	Intermediate Similarity	NPC213190
0.8073	Intermediate Similarity	NPC51154
0.8058	Intermediate Similarity	NPC144486
0.8058	Intermediate Similarity	NPC474022
0.8058	Intermediate Similarity	NPC476896
0.8056	Intermediate Similarity	NPC472987
0.8056	Intermediate Similarity	NPC473021
0.8056	Intermediate Similarity	NPC197231
0.8039	Intermediate Similarity	NPC280825
0.8039	Intermediate Similarity	NPC476895
0.8039	Intermediate Similarity	NPC234287
0.8039	Intermediate Similarity	NPC469725
0.8037	Intermediate Similarity	NPC476835
0.8037	Intermediate Similarity	NPC14630
0.8037	Intermediate Similarity	NPC157530
0.8037	Intermediate Similarity	NPC250089
0.802	Intermediate Similarity	NPC156377
0.8019	Intermediate Similarity	NPC470170
0.8019	Intermediate Similarity	NPC226642
0.8019	Intermediate Similarity	NPC473469
0.8019	Intermediate Similarity	NPC470169
0.8018	Intermediate Similarity	NPC290693
0.8018	Intermediate Similarity	NPC20979
0.8018	Intermediate Similarity	NPC100048
0.8018	Intermediate Similarity	NPC476690
0.8	Intermediate Similarity	NPC31354
0.8	Intermediate Similarity	NPC471633
0.8	Intermediate Similarity	NPC227260
0.8	Intermediate Similarity	NPC69576
0.8	Intermediate Similarity	NPC312774
0.8	Intermediate Similarity	NPC30687
0.8	Intermediate Similarity	NPC11548
0.8	Intermediate Similarity	NPC93352
0.8	Intermediate Similarity	NPC175
0.8	Intermediate Similarity	NPC84949
0.7982	Intermediate Similarity	NPC42171
0.7982	Intermediate Similarity	NPC19888
0.7982	Intermediate Similarity	NPC216595
0.7982	Intermediate Similarity	NPC473567
0.7981	Intermediate Similarity	NPC22634
0.7981	Intermediate Similarity	NPC136816
0.798	Intermediate Similarity	NPC48463
0.798	Intermediate Similarity	NPC59006
0.7979	Intermediate Similarity	NPC470611
0.7979	Intermediate Similarity	NPC296734
0.7963	Intermediate Similarity	NPC103627
0.7963	Intermediate Similarity	NPC170974
0.7963	Intermediate Similarity	NPC191439
0.7961	Intermediate Similarity	NPC7341
0.7961	Intermediate Similarity	NPC473200
0.7946	Intermediate Similarity	NPC10366
0.7944	Intermediate Similarity	NPC476540
0.7944	Intermediate Similarity	NPC476539
0.7944	Intermediate Similarity	NPC476541
0.7944	Intermediate Similarity	NPC475634
0.7944	Intermediate Similarity	NPC476538
0.7941	Intermediate Similarity	NPC274793
0.7941	Intermediate Similarity	NPC233649
0.7941	Intermediate Similarity	NPC470028
0.7941	Intermediate Similarity	NPC476893
0.7928	Intermediate Similarity	NPC477030
0.7928	Intermediate Similarity	NPC199428
0.7928	Intermediate Similarity	NPC477029
0.7928	Intermediate Similarity	NPC5311
0.7928	Intermediate Similarity	NPC193382
0.7928	Intermediate Similarity	NPC99620
0.7928	Intermediate Similarity	NPC310341
0.7925	Intermediate Similarity	NPC472898
0.7925	Intermediate Similarity	NPC242748
0.7925	Intermediate Similarity	NPC181845
0.7925	Intermediate Similarity	NPC472899
0.7925	Intermediate Similarity	NPC472900
0.7921	Intermediate Similarity	NPC476894
0.7909	Intermediate Similarity	NPC144068
0.7909	Intermediate Similarity	NPC476693
0.789	Intermediate Similarity	NPC65034
0.789	Intermediate Similarity	NPC208189
0.7885	Intermediate Similarity	NPC88000
0.7885	Intermediate Similarity	NPC4831
0.7885	Intermediate Similarity	NPC472023
0.7885	Intermediate Similarity	NPC309425
0.7885	Intermediate Similarity	NPC129372
0.7885	Intermediate Similarity	NPC47566
0.7885	Intermediate Similarity	NPC160734
0.7879	Intermediate Similarity	NPC473542
0.7876	Intermediate Similarity	NPC304260
0.7876	Intermediate Similarity	NPC5883
0.7876	Intermediate Similarity	NPC29639
0.7876	Intermediate Similarity	NPC44899
0.787	Intermediate Similarity	NPC477026
0.787	Intermediate Similarity	NPC28844
0.787	Intermediate Similarity	NPC474573
0.787	Intermediate Similarity	NPC475030
0.787	Intermediate Similarity	NPC70204
0.787	Intermediate Similarity	NPC40440
0.787	Intermediate Similarity	NPC42482
0.787	Intermediate Similarity	NPC306131
0.787	Intermediate Similarity	NPC477027
0.787	Intermediate Similarity	NPC473318
0.787	Intermediate Similarity	NPC473328
0.787	Intermediate Similarity	NPC475670
0.7864	Intermediate Similarity	NPC216260
0.7864	Intermediate Similarity	NPC309493
0.7864	Intermediate Similarity	NPC5358
0.7857	Intermediate Similarity	NPC196429
0.7857	Intermediate Similarity	NPC471351
0.7857	Intermediate Similarity	NPC84987
0.7857	Intermediate Similarity	NPC142066
0.7857	Intermediate Similarity	NPC203862
0.7857	Intermediate Similarity	NPC87250
0.7857	Intermediate Similarity	NPC152615
0.7857	Intermediate Similarity	NPC473852
0.7857	Intermediate Similarity	NPC77319
0.7857	Intermediate Similarity	NPC243196
0.7857	Intermediate Similarity	NPC309034
0.7857	Intermediate Similarity	NPC93883
0.7857	Intermediate Similarity	NPC471355
0.7857	Intermediate Similarity	NPC244402
0.7857	Intermediate Similarity	NPC99728
0.7857	Intermediate Similarity	NPC50305
0.7857	Intermediate Similarity	NPC471354
0.7857	Intermediate Similarity	NPC157376
0.7857	Intermediate Similarity	NPC471353
0.7857	Intermediate Similarity	NPC474418
0.7857	Intermediate Similarity	NPC473436
0.7857	Intermediate Similarity	NPC27507
0.7857	Intermediate Similarity	NPC158344
0.7857	Intermediate Similarity	NPC34390
0.785	Intermediate Similarity	NPC470166
0.785	Intermediate Similarity	NPC33053
0.785	Intermediate Similarity	NPC283829
0.785	Intermediate Similarity	NPC14704
0.785	Intermediate Similarity	NPC161676
0.785	Intermediate Similarity	NPC113044
0.785	Intermediate Similarity	NPC305423
0.785	Intermediate Similarity	NPC230507
0.785	Intermediate Similarity	NPC470432
0.7843	Intermediate Similarity	NPC476510
0.7843	Intermediate Similarity	NPC142264
0.783	Intermediate Similarity	NPC476360
0.783	Intermediate Similarity	NPC476361
0.783	Intermediate Similarity	NPC75608
0.7826	Intermediate Similarity	NPC115349
0.7822	Intermediate Similarity	NPC3359
0.7818	Intermediate Similarity	NPC477050
0.7818	Intermediate Similarity	NPC231797
0.7818	Intermediate Similarity	NPC475354
0.7812	Intermediate Similarity	NPC255882
0.781	Intermediate Similarity	NPC159036

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 NPC471112 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	270
0.1-0.2	2627
0.2-0.3	4206
0.3-0.4	1374
0.4-0.5	341
0.5-0.6	262
0.6-0.7	54
0.7-0.8	16
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
0.7788	Intermediate Similarity	NPD7327	Approved
0.7788	Intermediate Similarity	NPD7328	Approved
0.7766	Intermediate Similarity	NPD6928	Phase 2
0.7739	Intermediate Similarity	NPD8033	Approved
0.7719	Intermediate Similarity	NPD7516	Approved
0.7652	Intermediate Similarity	NPD8294	Approved
0.7652	Intermediate Similarity	NPD8377	Approved
0.7586	Intermediate Similarity	NPD8378	Approved
0.7586	Intermediate Similarity	NPD8335	Approved
0.7586	Intermediate Similarity	NPD8296	Approved
0.7586	Intermediate Similarity	NPD8380	Approved
0.7586	Intermediate Similarity	NPD8379	Approved
0.7549	Intermediate Similarity	NPD8171	Discontinued
0.7434	Intermediate Similarity	NPD8133	Approved
0.7333	Intermediate Similarity	NPD7507	Approved
0.7196	Intermediate Similarity	NPD7638	Approved
0.7154	Intermediate Similarity	NPD7319	Approved
0.7143	Intermediate Similarity	NPD7503	Approved
0.713	Intermediate Similarity	NPD7640	Approved
0.713	Intermediate Similarity	NPD7639	Approved
0.7054	Intermediate Similarity	NPD6412	Phase 2
0.6917	Remote Similarity	NPD6054	Approved
0.6917	Remote Similarity	NPD6059	Approved
0.6875	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6869	Remote Similarity	NPD7525	Registered
0.6803	Remote Similarity	NPD6370	Approved
0.68	Remote Similarity	NPD7736	Approved
0.6759	Remote Similarity	NPD7991	Discontinued
0.6731	Remote Similarity	NPD7524	Approved
0.6721	Remote Similarity	NPD6015	Approved
0.6721	Remote Similarity	NPD6016	Approved
0.6699	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6696	Remote Similarity	NPD7632	Discontinued
0.6694	Remote Similarity	NPD7492	Approved
0.6667	Remote Similarity	NPD5988	Approved
0.664	Remote Similarity	NPD6616	Approved
0.6636	Remote Similarity	NPD8034	Phase 2
0.6636	Remote Similarity	NPD8035	Phase 2
0.6633	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6613	Remote Similarity	NPD6067	Discontinued
0.6607	Remote Similarity	NPD4159	Approved
0.6587	Remote Similarity	NPD7078	Approved
0.6587	Remote Similarity	NPD8293	Discontinued
0.6571	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD6686	Approved
0.6535	Remote Similarity	NPD6033	Approved
0.6531	Remote Similarity	NPD7339	Approved
0.6531	Remote Similarity	NPD6942	Approved
0.6529	Remote Similarity	NPD7115	Discovery
0.6526	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.6505	Remote Similarity	NPD6695	Phase 3
0.6462	Remote Similarity	NPD8449	Approved
0.6442	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6436	Remote Similarity	NPD7645	Phase 2
0.6429	Remote Similarity	NPD4225	Approved
0.6412	Remote Similarity	NPD8450	Suspended
0.6393	Remote Similarity	NPD6009	Approved
0.6379	Remote Similarity	NPD6008	Approved
0.6356	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6331	Remote Similarity	NPD7625	Phase 1
0.63	Remote Similarity	NPD6933	Approved
0.6296	Remote Similarity	NPD6051	Approved
0.6281	Remote Similarity	NPD4632	Approved
0.6275	Remote Similarity	NPD6929	Approved
0.6271	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6262	Remote Similarity	NPD7750	Discontinued
0.626	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.624	Remote Similarity	NPD6319	Approved
0.622	Remote Similarity	NPD7604	Phase 2
0.6218	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6214	Remote Similarity	NPD6931	Approved
0.6214	Remote Similarity	NPD6930	Phase 2
0.6214	Remote Similarity	NPD4748	Discontinued
0.6198	Remote Similarity	NPD6882	Approved
0.619	Remote Similarity	NPD4788	Approved
0.6176	Remote Similarity	NPD6118	Approved
0.6176	Remote Similarity	NPD6114	Approved
0.6176	Remote Similarity	NPD6697	Approved
0.6176	Remote Similarity	NPD6115	Approved
0.6161	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD6902	Approved
0.6134	Remote Similarity	NPD7320	Approved
0.6132	Remote Similarity	NPD4786	Approved
0.6126	Remote Similarity	NPD6399	Phase 3
0.6122	Remote Similarity	NPD4787	Phase 1
0.6102	Remote Similarity	NPD5739	Approved
0.6102	Remote Similarity	NPD7128	Approved
0.6102	Remote Similarity	NPD6675	Approved
0.6102	Remote Similarity	NPD6402	Approved
0.61	Remote Similarity	NPD4784	Approved
0.61	Remote Similarity	NPD4785	Approved
0.61	Remote Similarity	NPD6926	Approved
0.61	Remote Similarity	NPD6924	Approved
0.6094	Remote Similarity	NPD8328	Phase 3
0.6078	Remote Similarity	NPD5776	Phase 2
0.6078	Remote Similarity	NPD6925	Approved
0.6066	Remote Similarity	NPD8297	Approved
0.6061	Remote Similarity	NPD4243	Approved
0.6036	Remote Similarity	NPD7087	Discontinued
0.6034	Remote Similarity	NPD5344	Discontinued
0.6033	Remote Similarity	NPD4634	Approved
0.6019	Remote Similarity	NPD7145	Approved
0.6	Remote Similarity	NPD5328	Approved
0.6	Remote Similarity	NPD6881	Approved
0.6	Remote Similarity	NPD6899	Approved
0.5982	Remote Similarity	NPD4202	Approved
0.598	Remote Similarity	NPD6117	Approved
0.595	Remote Similarity	NPD6373	Approved
0.595	Remote Similarity	NPD6372	Approved
0.5943	Remote Similarity	NPD3667	Approved
0.5941	Remote Similarity	NPD1811	Approved
0.5941	Remote Similarity	NPD1810	Approved
0.594	Remote Similarity	NPD5956	Approved
0.5938	Remote Similarity	NPD8513	Phase 3
0.5938	Remote Similarity	NPD5983	Phase 2
0.5938	Remote Similarity	NPD8516	Approved
0.5938	Remote Similarity	NPD8515	Approved
0.5938	Remote Similarity	NPD8517	Approved
0.5935	Remote Similarity	NPD6053	Discontinued
0.5929	Remote Similarity	NPD7748	Approved
0.5926	Remote Similarity	NPD6893	Approved
0.5922	Remote Similarity	NPD6932	Approved
0.5922	Remote Similarity	NPD6116	Phase 1
0.5917	Remote Similarity	NPD5697	Approved
0.5917	Remote Similarity	NPD5701	Approved
0.5913	Remote Similarity	NPD4755	Approved
0.5913	Remote Similarity	NPD6084	Phase 2
0.5913	Remote Similarity	NPD6083	Phase 2
0.5909	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.5905	Remote Similarity	NPD7514	Phase 3
0.5902	Remote Similarity	NPD6883	Approved
0.5902	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.5902	Remote Similarity	NPD7102	Approved
0.5902	Remote Similarity	NPD7290	Approved
0.59	Remote Similarity	NPD7151	Approved
0.59	Remote Similarity	NPD7152	Approved
0.59	Remote Similarity	NPD7150	Approved
0.5893	Remote Similarity	NPD7515	Phase 2
0.5893	Remote Similarity	NPD7637	Suspended
0.5893	Remote Similarity	NPD6079	Approved
0.5878	Remote Similarity	NPD6336	Discontinued
0.5872	Remote Similarity	NPD3618	Phase 1
0.5868	Remote Similarity	NPD6011	Approved
0.5859	Remote Similarity	NPD6923	Approved
0.5859	Remote Similarity	NPD6922	Approved
0.5854	Remote Similarity	NPD6649	Approved
0.5854	Remote Similarity	NPD6869	Approved
0.5854	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.5854	Remote Similarity	NPD8130	Phase 1
0.5854	Remote Similarity	NPD6650	Approved
0.5854	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.5854	Remote Similarity	NPD6617	Approved
0.5854	Remote Similarity	NPD6847	Approved
0.5851	Remote Similarity	NPD1145	Discontinued
0.5847	Remote Similarity	NPD5211	Phase 2
0.5833	Remote Similarity	NPD3665	Phase 1
0.5833	Remote Similarity	NPD3666	Approved
0.5833	Remote Similarity	NPD6640	Phase 3
0.5833	Remote Similarity	NPD3133	Approved
0.582	Remote Similarity	NPD6012	Approved
0.582	Remote Similarity	NPD6014	Approved
0.582	Remote Similarity	NPD6013	Approved
0.5812	Remote Similarity	NPD4700	Approved
0.5812	Remote Similarity	NPD5285	Approved
0.5812	Remote Similarity	NPD5286	Approved
0.5812	Remote Similarity	NPD4696	Approved
0.581	Remote Similarity	NPD6683	Phase 2
0.5804	Remote Similarity	NPD3168	Discontinued
0.58	Remote Similarity	NPD7143	Approved
0.58	Remote Similarity	NPD7144	Approved
0.5794	Remote Similarity	NPD6940	Discontinued
0.5789	Remote Similarity	NPD6001	Approved
0.5784	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.5776	Remote Similarity	NPD7902	Approved
0.5772	Remote Similarity	NPD6371	Approved
0.5769	Remote Similarity	NPD5125	Phase 3
0.5769	Remote Similarity	NPD5126	Approved
0.5766	Remote Similarity	NPD6903	Approved
0.5763	Remote Similarity	NPD5223	Approved
0.5755	Remote Similarity	NPD7509	Discontinued
0.5755	Remote Similarity	NPD7332	Phase 2
0.575	Remote Similarity	NPD5141	Approved
0.5743	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.5743	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.5738	Remote Similarity	NPD8174	Phase 2
0.5728	Remote Similarity	NPD4190	Phase 3
0.5728	Remote Similarity	NPD3703	Phase 2
0.5728	Remote Similarity	NPD5275	Approved
0.5727	Remote Similarity	NPD7334	Approved
0.5727	Remote Similarity	NPD6684	Approved
0.5727	Remote Similarity	NPD5330	Approved
0.5727	Remote Similarity	NPD6409	Approved
0.5727	Remote Similarity	NPD7146	Approved
0.5727	Remote Similarity	NPD7521	Approved
0.5714	Remote Similarity	NPD4633	Approved
0.5714	Remote Similarity	NPD5225	Approved
0.5714	Remote Similarity	NPD5224	Approved
0.5714	Remote Similarity	NPD4753	Phase 2
0.5714	Remote Similarity	NPD5226	Approved
0.5701	Remote Similarity	NPD6898	Phase 1

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