NPASS Compound

Structure

CID26557 OpenBabel06191715352D 32 35 0 0 1 0 0 0 0 0999 V2000 -5.4611 -0.6891 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9881 -1.1772 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2066 3.1333 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2205 3.0194 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1055 1.7661 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6367 -1.1650 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8124 -0.6891 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3288 -1.1833 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3288 0.7448 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4939 1.2268 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0360 -0.4807 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1638 -0.7013 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1039 2.7811 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5441 2.3325 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1638 0.2628 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.4939 -0.7013 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.8124 0.2628 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6180 -0.2191 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.1996 0.6495 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.1998 -1.0879 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.2598 0.8639 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.4939 0.2628 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.3983 -0.2715 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.8576 3.3822 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.6110 2.5750 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.6367 0.7387 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5414 -0.2190 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2476 1.8279 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 1.8006 1.4033 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.9881 0.7387 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.2599 -1.3023 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 6 1 0 0 0 0 2 12 1 0 0 0 0 3 13 1 0 0 0 0 4 14 1 0 0 0 0 5 21 1 0 0 0 0 6 7 1 0 0 0 0 7 17 1 0 0 0 0 8 12 2 0 0 0 0 8 16 1 0 0 0 0 9 15 1 0 0 0 0 9 22 1 0 0 0 0 10 28 1 0 0 0 0 11 23 1 0 0 0 0 11 29 1 0 0 0 0 12 15 1 0 0 0 0 13 24 2 0 0 0 0 13 28 1 0 0 0 0 14 25 2 0 0 0 0 14 30 1 0 0 0 0 15 31 1 1 0 0 0 16 22 1 6 0 0 0 16 32 1 0 0 0 0 17 26 2 0 0 0 0 17 31 1 0 0 0 0 18 19 1 0 0 0 0 18 20 1 0 0 0 0 18 27 1 1 0 0 0 19 21 1 6 0 0 0 19 30 1 0 0 0 0 20 23 1 6 0 0 0 20 32 1 0 0 0 0 21 22 1 1 0 0 0 22 10 1 1 0 0 0 23 21 1 1 0 0 0 23 29 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	452.2
Volume:	440.704
LogP:	2.2
LogD:	1.505
LogS:	-4.32
# Rotatable Bonds:	9
TPSA:	120.89
# H-Bond Aceptor:	9
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.276
Synthetic Accessibility Score:	6.029
Fsp3:	0.783
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.268
MDCK Permeability:	6.672299059573561e-05
Pgp-inhibitor:	0.822
Pgp-substrate:	0.997
Human Intestinal Absorption (HIA):	0.036
20% Bioavailability (F20%):	0.459
30% Bioavailability (F30%):	0.959

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.459
Plasma Protein Binding (PPB):	37.34639358520508%
Volume Distribution (VD):	1.103
Pgp-substrate:	38.29610061645508%

ADMET: Metabolism

CYP1A2-inhibitor:	0.029
CYP1A2-substrate:	0.102
CYP2C19-inhibitor:	0.043
CYP2C19-substrate:	0.493
CYP2C9-inhibitor:	0.028
CYP2C9-substrate:	0.029
CYP2D6-inhibitor:	0.031
CYP2D6-substrate:	0.084
CYP3A4-inhibitor:	0.598
CYP3A4-substrate:	0.358

ADMET: Excretion

Clearance (CL):	2.942
Half-life (T1/2):	0.724

ADMET: Toxicity

hERG Blockers:	0.062
Human Hepatotoxicity (H-HT):	0.564
Drug-inuced Liver Injury (DILI):	0.891
AMES Toxicity:	0.944
Rat Oral Acute Toxicity:	0.332
Maximum Recommended Daily Dose:	0.26
Skin Sensitization:	0.432
Carcinogencity:	0.088
Eye Corrosion:	0.004
Eye Irritation:	0.033
Respiratory Toxicity:	0.259

Download Data

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

Natural Product: NPC26557

Natural Product ID:	NPC26557
*Common Name:**	QAZLVSRKBUTUHB-MXINJKJASA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	QAZLVSRKBUTUHB-MXINJKJASA-N
Standard InCHI:	InChI=1S/C23H32O9/c1-6-7-17(26)31-15-9-22(10-28-13(3)24)16(8-12(15)2)32-20-18(27)19(30-14(4)25)21(22,5)23(20)11-29-23/h8,15-16,18-20,27H,6-7,9-11H2,1-5H3/t15-,16+,18+,19+,20+,21+,22+,23-/m0/s1
SMILES:	CCCC(=O)O[C@H]1C[C@@]2(COC(=O)C)[C@@H](C=C1C)O[C@@H]1[C@@H]([C@H]([C@@]2(C)[C@@]21CO2)OC(=O)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL356196
PubChem CID:	13797598
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001550] Sesquiterpenoids [CHEMONTID:0001789] Trichothecenes

*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
NPO11220	Fusarium sporotrichioides	Species	Nectriaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[1800633]
NPO11220	Fusarium sporotrichioides	Species	Nectriaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25475336]
NPO11220	Fusarium sporotrichioides	Species	Nectriaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8289061]
NPO10844	Lactarius pergamenus	Species	Russulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4524	Bosistoa pentacocca	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10844	Lactarius pergamenus	Species	Russulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11220	Fusarium sporotrichioides	Species	Nectriaceae	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	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1864	Cell Line	L5178Y	Mus musculus	LC50	=	0.0012	ug.mL-1	PMID[549810]

☑ 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 NPC26557 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	187
0.1-0.2	1179
0.2-0.3	4785
0.3-0.4	12672
0.4-0.5	9946
0.5-0.6	6960
0.6-0.7	6004
0.7-0.8	887
0.8-0.85	21
0.85-0.9	24
0.9-0.95	16
0.95-1	16

Similarity Score	Similarity Level	Natural Product ID
0.9894	High Similarity	NPC214714
0.9894	High Similarity	NPC200672
0.9894	High Similarity	NPC475956
0.9894	High Similarity	NPC252242
0.9789	High Similarity	NPC232515
0.9789	High Similarity	NPC260809
0.9789	High Similarity	NPC474783
0.9785	High Similarity	NPC79449
0.9785	High Similarity	NPC474957
0.9684	High Similarity	NPC475986
0.9677	High Similarity	NPC476057
0.9677	High Similarity	NPC347923
0.9574	High Similarity	NPC274458
0.9468	High Similarity	NPC182811
0.9462	High Similarity	NPC240838
0.9072	High Similarity	NPC79631
0.9	High Similarity	NPC93026
0.9	High Similarity	NPC469960
0.9	High Similarity	NPC29389
0.9	High Similarity	NPC265502
0.8911	High Similarity	NPC472263
0.8911	High Similarity	NPC469959
0.8911	High Similarity	NPC469957
0.8911	High Similarity	NPC108682
0.8857	High Similarity	NPC305044
0.8857	High Similarity	NPC265290
0.8846	High Similarity	NPC98038
0.8846	High Similarity	NPC313921
0.8835	High Similarity	NPC50223
0.883	High Similarity	NPC197107
0.8762	High Similarity	NPC101400
0.8762	High Similarity	NPC101965
0.8654	High Similarity	NPC41551
0.85	High Similarity	NPC13743
0.85	High Similarity	NPC98813
0.844	Intermediate Similarity	NPC475130
0.844	Intermediate Similarity	NPC474286
0.8411	Intermediate Similarity	NPC287075
0.84	Intermediate Similarity	NPC65700
0.8269	Intermediate Similarity	NPC470980
0.8269	Intermediate Similarity	NPC475290
0.8252	Intermediate Similarity	NPC123505
0.8173	Intermediate Similarity	NPC473577
0.8173	Intermediate Similarity	NPC475585
0.8173	Intermediate Similarity	NPC474550
0.8173	Intermediate Similarity	NPC169843
0.8056	Intermediate Similarity	NPC71680
0.8037	Intermediate Similarity	NPC77089
0.8	Intermediate Similarity	NPC103298
0.8	Intermediate Similarity	NPC80809
0.8	Intermediate Similarity	NPC475331
0.8	Intermediate Similarity	NPC281775
0.8	Intermediate Similarity	NPC181104
0.8	Intermediate Similarity	NPC201144
0.8	Intermediate Similarity	NPC288502
0.8	Intermediate Similarity	NPC475335
0.8	Intermediate Similarity	NPC121518
0.7982	Intermediate Similarity	NPC241477
0.7982	Intermediate Similarity	NPC126691
0.7981	Intermediate Similarity	NPC470972
0.7963	Intermediate Similarity	NPC15551
0.7925	Intermediate Similarity	NPC60315
0.7905	Intermediate Similarity	NPC474124
0.7905	Intermediate Similarity	NPC475334
0.7905	Intermediate Similarity	NPC473694
0.7905	Intermediate Similarity	NPC473523
0.7905	Intermediate Similarity	NPC475623
0.7885	Intermediate Similarity	NPC475617
0.7864	Intermediate Similarity	NPC222303
0.7843	Intermediate Similarity	NPC113433
0.7838	Intermediate Similarity	NPC216665
0.7835	Intermediate Similarity	NPC137253
0.7835	Intermediate Similarity	NPC477668
0.783	Intermediate Similarity	NPC473543
0.781	Intermediate Similarity	NPC475344
0.781	Intermediate Similarity	NPC472552
0.781	Intermediate Similarity	NPC476471
0.7807	Intermediate Similarity	NPC79579
0.7798	Intermediate Similarity	NPC472214
0.7798	Intermediate Similarity	NPC472215
0.7788	Intermediate Similarity	NPC230546
0.7778	Intermediate Similarity	NPC88701
0.7767	Intermediate Similarity	NPC210337
0.7736	Intermediate Similarity	NPC474775
0.7727	Intermediate Similarity	NPC474750
0.7719	Intermediate Similarity	NPC5292
0.7719	Intermediate Similarity	NPC278681
0.7714	Intermediate Similarity	NPC472554
0.7714	Intermediate Similarity	NPC280991
0.7714	Intermediate Similarity	NPC11974
0.7708	Intermediate Similarity	NPC231601
0.7706	Intermediate Similarity	NPC5475
0.7706	Intermediate Similarity	NPC173905
0.7706	Intermediate Similarity	NPC472216
0.7706	Intermediate Similarity	NPC284828
0.7699	Intermediate Similarity	NPC203862
0.7699	Intermediate Similarity	NPC290693
0.7692	Intermediate Similarity	NPC177232
0.7692	Intermediate Similarity	NPC212465
0.7685	Intermediate Similarity	NPC474421
0.7685	Intermediate Similarity	NPC326994
0.7685	Intermediate Similarity	NPC324327
0.7685	Intermediate Similarity	NPC72813
0.7685	Intermediate Similarity	NPC475781
0.7685	Intermediate Similarity	NPC194620
0.7679	Intermediate Similarity	NPC178289
0.7679	Intermediate Similarity	NPC106446
0.7679	Intermediate Similarity	NPC43213
0.7672	Intermediate Similarity	NPC115349
0.767	Intermediate Similarity	NPC57664
0.767	Intermediate Similarity	NPC88009
0.7652	Intermediate Similarity	NPC112936
0.7647	Intermediate Similarity	NPC472467
0.7642	Intermediate Similarity	NPC475038
0.7642	Intermediate Similarity	NPC109195
0.7632	Intermediate Similarity	NPC475401
0.7632	Intermediate Similarity	NPC153440
0.7632	Intermediate Similarity	NPC16701
0.7624	Intermediate Similarity	NPC235051
0.7619	Intermediate Similarity	NPC130792
0.7619	Intermediate Similarity	NPC473510
0.7619	Intermediate Similarity	NPC167974
0.7619	Intermediate Similarity	NPC79303
0.7619	Intermediate Similarity	NPC272223
0.7615	Intermediate Similarity	NPC14862
0.7615	Intermediate Similarity	NPC55972
0.7615	Intermediate Similarity	NPC327286
0.7615	Intermediate Similarity	NPC217921
0.7615	Intermediate Similarity	NPC48548
0.7615	Intermediate Similarity	NPC169888
0.7615	Intermediate Similarity	NPC135015
0.7615	Intermediate Similarity	NPC474664
0.7615	Intermediate Similarity	NPC233379
0.7615	Intermediate Similarity	NPC128795
0.7611	Intermediate Similarity	NPC310341
0.7611	Intermediate Similarity	NPC99620
0.7611	Intermediate Similarity	NPC199428
0.7611	Intermediate Similarity	NPC5311
0.7611	Intermediate Similarity	NPC193382
0.76	Intermediate Similarity	NPC299527
0.7596	Intermediate Similarity	NPC309503
0.7596	Intermediate Similarity	NPC239547
0.7596	Intermediate Similarity	NPC155319
0.7596	Intermediate Similarity	NPC205143
0.7596	Intermediate Similarity	NPC473244
0.7596	Intermediate Similarity	NPC91197
0.7596	Intermediate Similarity	NPC475033
0.7596	Intermediate Similarity	NPC475032
0.7596	Intermediate Similarity	NPC96597
0.7596	Intermediate Similarity	NPC86843
0.7596	Intermediate Similarity	NPC125551
0.7593	Intermediate Similarity	NPC186668
0.7593	Intermediate Similarity	NPC16313
0.7593	Intermediate Similarity	NPC220217
0.7593	Intermediate Similarity	NPC119855
0.7593	Intermediate Similarity	NPC9303
0.7586	Intermediate Similarity	NPC312481
0.7573	Intermediate Similarity	NPC93869
0.7573	Intermediate Similarity	NPC6765
0.757	Intermediate Similarity	NPC472821
0.757	Intermediate Similarity	NPC69171
0.757	Intermediate Similarity	NPC4620
0.757	Intermediate Similarity	NPC474165
0.757	Intermediate Similarity	NPC329834
0.7568	Intermediate Similarity	NPC470076
0.7565	Intermediate Similarity	NPC44899
0.7565	Intermediate Similarity	NPC304260
0.7565	Intermediate Similarity	NPC213761
0.7565	Intermediate Similarity	NPC29639
0.7565	Intermediate Similarity	NPC270850
0.7565	Intermediate Similarity	NPC5883
0.7565	Intermediate Similarity	NPC35171
0.7565	Intermediate Similarity	NPC305260
0.7565	Intermediate Similarity	NPC291820
0.7565	Intermediate Similarity	NPC477092
0.7565	Intermediate Similarity	NPC81222
0.7553	Intermediate Similarity	NPC477089
0.7549	Intermediate Similarity	NPC470187
0.7545	Intermediate Similarity	NPC475922
0.7545	Intermediate Similarity	NPC40728
0.7545	Intermediate Similarity	NPC316974
0.7545	Intermediate Similarity	NPC128133
0.7545	Intermediate Similarity	NPC187876
0.7545	Intermediate Similarity	NPC15218
0.7544	Intermediate Similarity	NPC158344
0.7544	Intermediate Similarity	NPC99728
0.7544	Intermediate Similarity	NPC50305
0.7544	Intermediate Similarity	NPC309034
0.7544	Intermediate Similarity	NPC84987
0.7544	Intermediate Similarity	NPC93883
0.7544	Intermediate Similarity	NPC473852
0.7544	Intermediate Similarity	NPC244402
0.7544	Intermediate Similarity	NPC142066
0.7544	Intermediate Similarity	NPC243196
0.7544	Intermediate Similarity	NPC185287
0.7544	Intermediate Similarity	NPC471355
0.7544	Intermediate Similarity	NPC152615
0.7544	Intermediate Similarity	NPC471351
0.7544	Intermediate Similarity	NPC475305
0.7544	Intermediate Similarity	NPC471353

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 NPC26557 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	149
0.1-0.2	1525
0.2-0.3	4058
0.3-0.4	2395
0.4-0.5	574
0.5-0.6	269
0.6-0.7	172
0.7-0.8	8
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
0.77	Intermediate Similarity	NPD46	Approved
0.77	Intermediate Similarity	NPD6698	Approved
0.7524	Intermediate Similarity	NPD7638	Approved
0.7478	Intermediate Similarity	NPD7328	Approved
0.7478	Intermediate Similarity	NPD7327	Approved
0.7453	Intermediate Similarity	NPD7640	Approved
0.7453	Intermediate Similarity	NPD7639	Approved
0.7436	Intermediate Similarity	NPD7503	Approved
0.7436	Intermediate Similarity	NPD8033	Approved
0.7414	Intermediate Similarity	NPD7516	Approved
0.7353	Intermediate Similarity	NPD7838	Discovery
0.735	Intermediate Similarity	NPD8377	Approved
0.735	Intermediate Similarity	NPD8294	Approved
0.7333	Intermediate Similarity	NPD7507	Approved
0.7297	Intermediate Similarity	NPD6686	Approved
0.7288	Intermediate Similarity	NPD8335	Approved
0.7288	Intermediate Similarity	NPD8296	Approved
0.7288	Intermediate Similarity	NPD8380	Approved
0.7288	Intermediate Similarity	NPD8378	Approved
0.7288	Intermediate Similarity	NPD8379	Approved
0.7232	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7207	Intermediate Similarity	NPD6412	Phase 2
0.7193	Intermediate Similarity	NPD6053	Discontinued
0.7168	Intermediate Similarity	NPD6371	Approved
0.7154	Intermediate Similarity	NPD7319	Approved
0.7094	Intermediate Similarity	NPD7115	Discovery
0.7064	Intermediate Similarity	NPD5344	Discontinued
0.7059	Intermediate Similarity	NPD6319	Approved
0.7059	Intermediate Similarity	NPD4250	Approved
0.7059	Intermediate Similarity	NPD4251	Approved
0.7054	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD4819	Approved
0.7041	Intermediate Similarity	NPD5790	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD4821	Approved
0.7041	Intermediate Similarity	NPD4820	Approved
0.7041	Intermediate Similarity	NPD4822	Approved
0.703	Intermediate Similarity	NPD6082	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.6961	Remote Similarity	NPD4249	Approved
0.6923	Remote Similarity	NPD6051	Approved
0.6897	Remote Similarity	NPD8297	Approved
0.6881	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6881	Remote Similarity	NPD4225	Approved
0.6847	Remote Similarity	NPD7632	Discontinued
0.6838	Remote Similarity	NPD8133	Approved
0.6838	Remote Similarity	NPD4632	Approved
0.6837	Remote Similarity	NPD4271	Approved
0.6837	Remote Similarity	NPD4268	Approved
0.6814	Remote Similarity	NPD5739	Approved
0.6814	Remote Similarity	NPD6402	Approved
0.6814	Remote Similarity	NPD6675	Approved
0.6814	Remote Similarity	NPD7128	Approved
0.681	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6792	Remote Similarity	NPD7637	Suspended
0.6789	Remote Similarity	NPD6083	Phase 2
0.6789	Remote Similarity	NPD6084	Phase 2
0.6783	Remote Similarity	NPD6372	Approved
0.6783	Remote Similarity	NPD6373	Approved
0.6754	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6733	Remote Similarity	NPD6435	Approved
0.6731	Remote Similarity	NPD7524	Approved
0.6721	Remote Similarity	NPD8516	Approved
0.6721	Remote Similarity	NPD8517	Approved
0.6721	Remote Similarity	NPD8515	Approved
0.6721	Remote Similarity	NPD8513	Phase 3
0.6696	Remote Similarity	NPD7320	Approved
0.6696	Remote Similarity	NPD6881	Approved
0.6696	Remote Similarity	NPD6899	Approved
0.6694	Remote Similarity	NPD7492	Approved
0.6667	Remote Similarity	NPD6008	Approved
0.6667	Remote Similarity	NPD6649	Approved
0.6667	Remote Similarity	NPD6650	Approved
0.6667	Remote Similarity	NPD6648	Approved
0.664	Remote Similarity	NPD6616	Approved
0.6639	Remote Similarity	NPD6059	Approved
0.6639	Remote Similarity	NPD6054	Approved
0.6636	Remote Similarity	NPD7983	Approved
0.6613	Remote Similarity	NPD7604	Phase 2
0.661	Remote Similarity	NPD6882	Approved
0.6609	Remote Similarity	NPD5697	Approved
0.6609	Remote Similarity	NPD5701	Approved
0.6606	Remote Similarity	NPD5695	Phase 3
0.6602	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6587	Remote Similarity	NPD8293	Discontinued
0.6587	Remote Similarity	NPD7078	Approved
0.6581	Remote Similarity	NPD7290	Approved
0.6581	Remote Similarity	NPD6883	Approved
0.6581	Remote Similarity	NPD7102	Approved
0.6574	Remote Similarity	NPD6399	Phase 3
0.6552	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6542	Remote Similarity	NPD5785	Approved
0.6535	Remote Similarity	NPD5368	Approved
0.6535	Remote Similarity	NPD7736	Approved
0.6532	Remote Similarity	NPD6370	Approved
0.6529	Remote Similarity	NPD6009	Approved
0.6525	Remote Similarity	NPD6869	Approved
0.6525	Remote Similarity	NPD6617	Approved
0.6525	Remote Similarity	NPD8130	Phase 1
0.6525	Remote Similarity	NPD6847	Approved
0.6505	Remote Similarity	NPD5362	Discontinued
0.6505	Remote Similarity	NPD7154	Phase 3
0.6505	Remote Similarity	NPD6695	Phase 3
0.6496	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6496	Remote Similarity	NPD6012	Approved
0.6496	Remote Similarity	NPD6013	Approved
0.6496	Remote Similarity	NPD6014	Approved
0.6476	Remote Similarity	NPD7146	Approved
0.6476	Remote Similarity	NPD5330	Approved
0.6476	Remote Similarity	NPD7521	Approved
0.6476	Remote Similarity	NPD6684	Approved
0.6476	Remote Similarity	NPD7334	Approved
0.6476	Remote Similarity	NPD6409	Approved
0.646	Remote Similarity	NPD4159	Approved
0.6457	Remote Similarity	NPD8074	Phase 3
0.6452	Remote Similarity	NPD5983	Phase 2
0.6452	Remote Similarity	NPD6016	Approved
0.6452	Remote Similarity	NPD6015	Approved
0.6449	Remote Similarity	NPD1695	Approved
0.6442	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6441	Remote Similarity	NPD4634	Approved
0.6429	Remote Similarity	NPD5696	Approved
0.6422	Remote Similarity	NPD5779	Approved
0.6422	Remote Similarity	NPD5778	Approved
0.641	Remote Similarity	NPD6011	Approved
0.64	Remote Similarity	NPD5988	Approved
0.6387	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6385	Remote Similarity	NPD7260	Phase 2
0.6378	Remote Similarity	NPD6336	Discontinued
0.6355	Remote Similarity	NPD6903	Approved
0.6355	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6346	Remote Similarity	NPD5332	Approved
0.6346	Remote Similarity	NPD5331	Approved
0.6339	Remote Similarity	NPD4755	Approved
0.6337	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.633	Remote Similarity	NPD6411	Approved
0.633	Remote Similarity	NPD5693	Phase 1
0.6311	Remote Similarity	NPD5369	Approved
0.6311	Remote Similarity	NPD4790	Discontinued
0.6306	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6296	Remote Similarity	NPD4753	Phase 2
0.6286	Remote Similarity	NPD3666	Approved
0.6286	Remote Similarity	NPD3665	Phase 1
0.6286	Remote Similarity	NPD3133	Approved
0.6273	Remote Similarity	NPD4202	Approved
0.6262	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6262	Remote Similarity	NPD7750	Discontinued
0.6261	Remote Similarity	NPD5211	Phase 2
0.625	Remote Similarity	NPD4269	Approved
0.625	Remote Similarity	NPD4270	Approved
0.625	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.6228	Remote Similarity	NPD4696	Approved
0.6228	Remote Similarity	NPD5286	Approved
0.6228	Remote Similarity	NPD4700	Approved
0.6228	Remote Similarity	NPD5285	Approved
0.6226	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6226	Remote Similarity	NPD1694	Approved
0.622	Remote Similarity	NPD8328	Phase 3
0.622	Remote Similarity	NPD6067	Discontinued
0.6214	Remote Similarity	NPD6931	Approved
0.6214	Remote Similarity	NPD7525	Registered
0.6214	Remote Similarity	NPD6930	Phase 2
0.6186	Remote Similarity	NPD6685	Approved
0.6182	Remote Similarity	NPD5281	Approved
0.6182	Remote Similarity	NPD5284	Approved
0.6179	Remote Similarity	NPD6274	Approved
0.6168	Remote Similarity	NPD5786	Approved
0.6168	Remote Similarity	NPD6098	Approved
0.616	Remote Similarity	NPD7100	Approved
0.616	Remote Similarity	NPD7101	Approved
0.6154	Remote Similarity	NPD6033	Approved
0.6154	Remote Similarity	NPD5141	Approved
0.6147	Remote Similarity	NPD6101	Approved
0.6147	Remote Similarity	NPD6673	Approved
0.6147	Remote Similarity	NPD6904	Approved
0.6147	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6147	Remote Similarity	NPD6080	Approved
0.6139	Remote Similarity	NPD6933	Approved
0.6139	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6132	Remote Similarity	NPD4786	Approved
0.6129	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6124	Remote Similarity	NPD8273	Phase 1
0.6121	Remote Similarity	NPD5224	Approved
0.6121	Remote Similarity	NPD4633	Approved
0.6121	Remote Similarity	NPD5226	Approved
0.6121	Remote Similarity	NPD5225	Approved
0.6117	Remote Similarity	NPD6929	Approved
0.6105	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6102	Remote Similarity	NPD4768	Approved
0.6102	Remote Similarity	NPD4767	Approved
0.6095	Remote Similarity	NPD3667	Approved
0.6095	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.609	Remote Similarity	NPD6845	Suspended
0.608	Remote Similarity	NPD6335	Approved
0.6075	Remote Similarity	NPD5363	Approved
0.6071	Remote Similarity	NPD7748	Approved
0.6071	Remote Similarity	NPD5282	Discontinued
0.6068	Remote Similarity	NPD5175	Approved
0.6068	Remote Similarity	NPD5174	Approved
0.6063	Remote Similarity	NPD6909	Approved
0.6063	Remote Similarity	NPD6921	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