NPASS Compound

Structure

NPC232515 OpenBabel07101718282D 31 34 0 0 1 0 0 0 0 0999 V2000 1.4543 -0.7365 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3908 -3.7028 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1022 -1.0078 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6176 -0.1684 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9568 1.8330 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0105 -0.6008 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0105 0.7950 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2937 -0.5232 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6859 -1.1555 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4205 -0.8732 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6149 -0.2519 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8113 -2.8296 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6149 0.4461 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.5939 -0.2519 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.2937 0.4461 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5205 0.1381 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.1000 1.0113 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.8200 -0.5317 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.1330 -1.0078 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1396 0.8812 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.5939 0.4461 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.9665 -0.0724 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.7778 -2.7571 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.1330 0.9307 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4742 -0.0350 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5593 1.8648 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.1330 -1.9770 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2653 -2.0288 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 1.4543 0.9307 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.1396 -0.6870 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 11 1 0 0 0 0 2 12 1 0 0 0 0 3 19 1 0 0 0 0 4 19 1 0 0 0 0 5 20 1 0 0 0 0 6 11 2 0 0 0 0 6 14 1 0 0 0 0 7 13 1 0 0 0 0 7 21 1 0 0 0 0 8 15 1 0 0 0 0 8 19 1 0 0 0 0 9 28 1 0 0 0 0 10 22 1 0 0 0 0 10 29 1 0 0 0 0 11 13 1 0 0 0 0 12 23 2 0 0 0 0 12 28 1 0 0 0 0 13 30 1 6 0 0 0 14 21 1 1 0 0 0 14 31 1 0 0 0 0 15 24 2 0 0 0 0 15 30 1 0 0 0 0 16 17 1 0 0 0 0 16 18 1 0 0 0 0 16 25 1 6 0 0 0 17 20 1 1 0 0 0 17 26 1 0 0 0 0 18 22 1 1 0 0 0 18 31 1 0 0 0 0 19 27 1 0 0 0 0 20 21 1 6 0 0 0 21 9 1 6 0 0 0 22 20 1 6 0 0 0 22 29 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	440.2
Volume:	426.045
LogP:	1.336
LogD:	0.662
LogS:	-3.685
# Rotatable Bonds:	7
TPSA:	135.05
# H-Bond Aceptor:	9
# H-Bond Donor:	3
# Rings:	4
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.312
Synthetic Accessibility Score:	6.235
Fsp3:	0.818
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:	-5.452
MDCK Permeability:	8.726905798539519e-05
Pgp-inhibitor:	0.019
Pgp-substrate:	0.998
Human Intestinal Absorption (HIA):	0.562
20% Bioavailability (F20%):	0.887
30% Bioavailability (F30%):	0.924

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.119
Plasma Protein Binding (PPB):	27.437881469726562%
Volume Distribution (VD):	0.46
Pgp-substrate:	52.29761505126953%

ADMET: Metabolism

CYP1A2-inhibitor:	0.012
CYP1A2-substrate:	0.111
CYP2C19-inhibitor:	0.026
CYP2C19-substrate:	0.578
CYP2C9-inhibitor:	0.015
CYP2C9-substrate:	0.04
CYP2D6-inhibitor:	0.012
CYP2D6-substrate:	0.085
CYP3A4-inhibitor:	0.177
CYP3A4-substrate:	0.226

ADMET: Excretion

Clearance (CL):	2.889
Half-life (T1/2):	0.858

ADMET: Toxicity

hERG Blockers:	0.034
Human Hepatotoxicity (H-HT):	0.442
Drug-inuced Liver Injury (DILI):	0.803
AMES Toxicity:	0.937
Rat Oral Acute Toxicity:	0.402
Maximum Recommended Daily Dose:	0.227
Skin Sensitization:	0.304
Carcinogencity:	0.133
Eye Corrosion:	0.003
Eye Irritation:	0.012
Respiratory Toxicity:	0.108

Download Data

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

Natural Product: NPC232515

Natural Product ID:	NPC232515
*Common Name:**	OJBCMLLFVXXDGS-QDSVCGCGSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	OJBCMLLFVXXDGS-QDSVCGCGSA-N
Standard InCHI:	InChI=1S/C22H32O9/c1-11-6-14-21(9-28-12(2)23,7-13(11)30-15(24)8-19(3,4)27)20(5)17(26)16(25)18(31-14)22(20)10-29-22/h6,13-14,16-18,25-27H,7-10H2,1-5H3/t13-,14+,16+,17+,18+,20+,21+,22-/m0/s1
SMILES:	O=C(CC(O)(C)C)O[C@H]1C[C@@]2(COC(=O)C)[C@@H](C=C1C)O[C@H]1[C@]3([C@]2(C)[C@H](O)[C@H]1O)CO3
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL486001
PubChem CID:	44559327
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
NPO15511	Fusarium heterosporum	Species	Nectriaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7264681]
NPO15511	Fusarium heterosporum	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
ED50	1
LD50	1

Activity Type	# Activity
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT673	Organism	Gallus gallus	Gallus gallus	LD50	=	8.5	mg.kg-1	PMID[488795]
NPT419	Organism	Oryctolagus cuniculus	Oryctolagus cuniculus	ED50	>	1.28	ug	PMID[488795]

☑ 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 NPC232515 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	195
0.1-0.2	1260
0.2-0.3	4764
0.3-0.4	11912
0.4-0.5	10797
0.5-0.6	7163
0.6-0.7	5722
0.7-0.8	804
0.8-0.85	22
0.85-0.9	40
0.9-0.95	5
0.95-1	13

Similarity Score	Similarity Level	Natural Product ID
0.9895	High Similarity	NPC475986
0.9789	High Similarity	NPC26557
0.9688	High Similarity	NPC475956
0.9688	High Similarity	NPC200672
0.9688	High Similarity	NPC214714
0.9688	High Similarity	NPC252242
0.9588	High Similarity	NPC260809
0.9588	High Similarity	NPC474783
0.9579	High Similarity	NPC79449
0.9579	High Similarity	NPC474957
0.9474	High Similarity	NPC347923
0.9474	High Similarity	NPC476057
0.9375	High Similarity	NPC274458
0.9271	High Similarity	NPC182811
0.9263	High Similarity	NPC240838
0.8889	High Similarity	NPC79631
0.8824	High Similarity	NPC93026
0.8824	High Similarity	NPC469960
0.8824	High Similarity	NPC265502
0.8824	High Similarity	NPC29389
0.8738	High Similarity	NPC469957
0.8738	High Similarity	NPC469959
0.8738	High Similarity	NPC108682
0.8738	High Similarity	NPC472263
0.8692	High Similarity	NPC305044
0.8692	High Similarity	NPC265290
0.8679	High Similarity	NPC98038
0.8679	High Similarity	NPC313921
0.8667	High Similarity	NPC50223
0.8646	High Similarity	NPC197107
0.8624	High Similarity	NPC475130
0.8624	High Similarity	NPC474286
0.8598	High Similarity	NPC101400
0.8598	High Similarity	NPC101965
0.8491	Intermediate Similarity	NPC41551
0.8333	Intermediate Similarity	NPC98813
0.8333	Intermediate Similarity	NPC13743
0.8257	Intermediate Similarity	NPC287075
0.8235	Intermediate Similarity	NPC65700
0.8113	Intermediate Similarity	NPC470980
0.8113	Intermediate Similarity	NPC475290
0.8095	Intermediate Similarity	NPC123505
0.8019	Intermediate Similarity	NPC169843
0.8019	Intermediate Similarity	NPC475585
0.8019	Intermediate Similarity	NPC474550
0.8019	Intermediate Similarity	NPC473577
0.7909	Intermediate Similarity	NPC71680
0.789	Intermediate Similarity	NPC77089
0.7885	Intermediate Similarity	NPC212465
0.7885	Intermediate Similarity	NPC177232
0.787	Intermediate Similarity	NPC474421
0.787	Intermediate Similarity	NPC194620
0.787	Intermediate Similarity	NPC326994
0.787	Intermediate Similarity	NPC324327
0.787	Intermediate Similarity	NPC72813
0.785	Intermediate Similarity	NPC121518
0.785	Intermediate Similarity	NPC181104
0.785	Intermediate Similarity	NPC103298
0.785	Intermediate Similarity	NPC201144
0.785	Intermediate Similarity	NPC288502
0.785	Intermediate Similarity	NPC475331
0.785	Intermediate Similarity	NPC80809
0.785	Intermediate Similarity	NPC475335
0.7843	Intermediate Similarity	NPC281775
0.7838	Intermediate Similarity	NPC126691
0.7838	Intermediate Similarity	NPC241477
0.783	Intermediate Similarity	NPC470972
0.7818	Intermediate Similarity	NPC15551
0.7807	Intermediate Similarity	NPC475401
0.7798	Intermediate Similarity	NPC55972
0.7798	Intermediate Similarity	NPC169888
0.7798	Intermediate Similarity	NPC14862
0.7798	Intermediate Similarity	NPC327286
0.7798	Intermediate Similarity	NPC233379
0.7798	Intermediate Similarity	NPC474664
0.7778	Intermediate Similarity	NPC60315
0.7778	Intermediate Similarity	NPC16313
0.7778	Intermediate Similarity	NPC9303
0.7757	Intermediate Similarity	NPC69171
0.7757	Intermediate Similarity	NPC475623
0.7757	Intermediate Similarity	NPC474124
0.7757	Intermediate Similarity	NPC475334
0.7757	Intermediate Similarity	NPC473694
0.7757	Intermediate Similarity	NPC473523
0.7757	Intermediate Similarity	NPC474165
0.7757	Intermediate Similarity	NPC4620
0.7739	Intermediate Similarity	NPC477092
0.7736	Intermediate Similarity	NPC475617
0.7727	Intermediate Similarity	NPC15218
0.7727	Intermediate Similarity	NPC475922
0.7719	Intermediate Similarity	NPC475305
0.7714	Intermediate Similarity	NPC222303
0.7699	Intermediate Similarity	NPC216665
0.7692	Intermediate Similarity	NPC107493
0.7692	Intermediate Similarity	NPC470265
0.7692	Intermediate Similarity	NPC23786
0.7692	Intermediate Similarity	NPC113433
0.7685	Intermediate Similarity	NPC220964
0.7685	Intermediate Similarity	NPC475676
0.7685	Intermediate Similarity	NPC473543
0.7679	Intermediate Similarity	NPC317687
0.7677	Intermediate Similarity	NPC137253
0.7677	Intermediate Similarity	NPC477668
0.7672	Intermediate Similarity	NPC472004
0.7672	Intermediate Similarity	NPC79579
0.7664	Intermediate Similarity	NPC183571
0.7664	Intermediate Similarity	NPC476471
0.7664	Intermediate Similarity	NPC475344
0.7664	Intermediate Similarity	NPC472552
0.7658	Intermediate Similarity	NPC472215
0.7658	Intermediate Similarity	NPC161816
0.7658	Intermediate Similarity	NPC472214
0.7658	Intermediate Similarity	NPC115257
0.7642	Intermediate Similarity	NPC230546
0.7636	Intermediate Similarity	NPC88701
0.7636	Intermediate Similarity	NPC94377
0.7632	Intermediate Similarity	NPC470075
0.7632	Intermediate Similarity	NPC277583
0.7619	Intermediate Similarity	NPC210337
0.7615	Intermediate Similarity	NPC475802
0.7607	Intermediate Similarity	NPC46570
0.7607	Intermediate Similarity	NPC67569
0.7596	Intermediate Similarity	NPC471786
0.7596	Intermediate Similarity	NPC37603
0.7593	Intermediate Similarity	NPC474775
0.7589	Intermediate Similarity	NPC474750
0.7589	Intermediate Similarity	NPC317107
0.7586	Intermediate Similarity	NPC5292
0.7586	Intermediate Similarity	NPC278681
0.757	Intermediate Similarity	NPC472554
0.757	Intermediate Similarity	NPC280991
0.757	Intermediate Similarity	NPC11974
0.7568	Intermediate Similarity	NPC472216
0.7568	Intermediate Similarity	NPC284828
0.7568	Intermediate Similarity	NPC5475
0.7568	Intermediate Similarity	NPC173905
0.7565	Intermediate Similarity	NPC203862
0.7565	Intermediate Similarity	NPC290693
0.7563	Intermediate Similarity	NPC8374
0.7551	Intermediate Similarity	NPC231601
0.7545	Intermediate Similarity	NPC475781
0.7544	Intermediate Similarity	NPC178289
0.7544	Intermediate Similarity	NPC106446
0.7544	Intermediate Similarity	NPC43213
0.7542	Intermediate Similarity	NPC269642
0.7542	Intermediate Similarity	NPC115349
0.7541	Intermediate Similarity	NPC173347
0.7524	Intermediate Similarity	NPC170527
0.7524	Intermediate Similarity	NPC57664
0.7524	Intermediate Similarity	NPC88009
0.7523	Intermediate Similarity	NPC146731
0.7523	Intermediate Similarity	NPC296950
0.7522	Intermediate Similarity	NPC473877
0.7521	Intermediate Similarity	NPC311534
0.7521	Intermediate Similarity	NPC112936
0.7521	Intermediate Similarity	NPC474370
0.75	Intermediate Similarity	NPC16701
0.75	Intermediate Similarity	NPC471234
0.75	Intermediate Similarity	NPC49393
0.75	Intermediate Similarity	NPC475038
0.75	Intermediate Similarity	NPC288679
0.75	Intermediate Similarity	NPC153440
0.75	Intermediate Similarity	NPC472467
0.75	Intermediate Similarity	NPC13710
0.75	Intermediate Similarity	NPC109195
0.75	Intermediate Similarity	NPC474709
0.7479	Intermediate Similarity	NPC469789
0.7478	Intermediate Similarity	NPC5311
0.7478	Intermediate Similarity	NPC199428
0.7478	Intermediate Similarity	NPC193382
0.7478	Intermediate Similarity	NPC99620
0.7478	Intermediate Similarity	NPC310341
0.7477	Intermediate Similarity	NPC128795
0.7477	Intermediate Similarity	NPC473510
0.7477	Intermediate Similarity	NPC135015
0.7477	Intermediate Similarity	NPC167974
0.7477	Intermediate Similarity	NPC272223
0.7477	Intermediate Similarity	NPC48548
0.7477	Intermediate Similarity	NPC308191
0.7477	Intermediate Similarity	NPC79303
0.7477	Intermediate Similarity	NPC217921
0.7477	Intermediate Similarity	NPC130792
0.7476	Intermediate Similarity	NPC235051
0.7459	Intermediate Similarity	NPC470880
0.7458	Intermediate Similarity	NPC312481
0.7458	Intermediate Similarity	NPC472000
0.7458	Intermediate Similarity	NPC471999
0.7455	Intermediate Similarity	NPC220217
0.7455	Intermediate Similarity	NPC186668
0.7455	Intermediate Similarity	NPC179891
0.7455	Intermediate Similarity	NPC119855
0.7453	Intermediate Similarity	NPC309503
0.7453	Intermediate Similarity	NPC473244
0.7453	Intermediate Similarity	NPC475033
0.7453	Intermediate Similarity	NPC91197
0.7453	Intermediate Similarity	NPC239547
0.7453	Intermediate Similarity	NPC96597
0.7453	Intermediate Similarity	NPC155319
0.7453	Intermediate Similarity	NPC86843
0.7453	Intermediate Similarity	NPC125551

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 NPC232515 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	157
0.1-0.2	1593
0.2-0.3	4023
0.3-0.4	2366
0.4-0.5	566
0.5-0.6	275
0.6-0.7	163
0.7-0.8	7
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
0.7549	Intermediate Similarity	NPD6698	Approved
0.7549	Intermediate Similarity	NPD46	Approved
0.7383	Intermediate Similarity	NPD7638	Approved
0.735	Intermediate Similarity	NPD7328	Approved
0.735	Intermediate Similarity	NPD7327	Approved
0.7345	Intermediate Similarity	NPD6371	Approved
0.7317	Intermediate Similarity	NPD7319	Approved
0.7315	Intermediate Similarity	NPD7640	Approved
0.7315	Intermediate Similarity	NPD7639	Approved
0.7311	Intermediate Similarity	NPD7503	Approved
0.7311	Intermediate Similarity	NPD8033	Approved
0.7288	Intermediate Similarity	NPD7516	Approved
0.7265	Intermediate Similarity	NPD7115	Discovery
0.7232	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7227	Intermediate Similarity	NPD6319	Approved
0.7227	Intermediate Similarity	NPD8377	Approved
0.7227	Intermediate Similarity	NPD8294	Approved
0.7213	Intermediate Similarity	NPD7507	Approved
0.7212	Intermediate Similarity	NPD7838	Discovery
0.7168	Intermediate Similarity	NPD6686	Approved
0.7167	Intermediate Similarity	NPD8379	Approved
0.7167	Intermediate Similarity	NPD8296	Approved
0.7167	Intermediate Similarity	NPD8335	Approved
0.7167	Intermediate Similarity	NPD8380	Approved
0.7167	Intermediate Similarity	NPD8378	Approved
0.7105	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.708	Intermediate Similarity	NPD6412	Phase 2
0.7069	Intermediate Similarity	NPD6053	Discontinued
0.7064	Intermediate Similarity	NPD4225	Approved
0.6981	Remote Similarity	NPD7637	Suspended
0.6937	Remote Similarity	NPD5344	Discontinued
0.6923	Remote Similarity	NPD4251	Approved
0.6923	Remote Similarity	NPD4250	Approved
0.69	Remote Similarity	NPD4819	Approved
0.69	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.69	Remote Similarity	NPD4822	Approved
0.69	Remote Similarity	NPD4820	Approved
0.69	Remote Similarity	NPD4821	Approved
0.6897	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6893	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6885	Remote Similarity	NPD8513	Phase 3
0.6885	Remote Similarity	NPD8516	Approved
0.6885	Remote Similarity	NPD8515	Approved
0.6885	Remote Similarity	NPD8517	Approved
0.6855	Remote Similarity	NPD7492	Approved
0.6827	Remote Similarity	NPD4249	Approved
0.6822	Remote Similarity	NPD7983	Approved
0.6803	Remote Similarity	NPD6054	Approved
0.6803	Remote Similarity	NPD6059	Approved
0.68	Remote Similarity	NPD6616	Approved
0.6792	Remote Similarity	NPD6051	Approved
0.678	Remote Similarity	NPD8297	Approved
0.6757	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6746	Remote Similarity	NPD8293	Discontinued
0.6746	Remote Similarity	NPD7078	Approved
0.6729	Remote Similarity	NPD5785	Approved
0.6726	Remote Similarity	NPD7632	Discontinued
0.6724	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6723	Remote Similarity	NPD8133	Approved
0.6723	Remote Similarity	NPD4632	Approved
0.67	Remote Similarity	NPD4268	Approved
0.67	Remote Similarity	NPD4271	Approved
0.6696	Remote Similarity	NPD6675	Approved
0.6696	Remote Similarity	NPD7128	Approved
0.6696	Remote Similarity	NPD6402	Approved
0.6696	Remote Similarity	NPD5739	Approved
0.6695	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6694	Remote Similarity	NPD6370	Approved
0.6693	Remote Similarity	NPD7736	Approved
0.6667	Remote Similarity	NPD6372	Approved
0.6667	Remote Similarity	NPD6083	Phase 2
0.6667	Remote Similarity	NPD6084	Phase 2
0.6667	Remote Similarity	NPD6373	Approved
0.6638	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6614	Remote Similarity	NPD8074	Phase 3
0.6613	Remote Similarity	NPD6016	Approved
0.6613	Remote Similarity	NPD6015	Approved
0.661	Remote Similarity	NPD4634	Approved
0.6606	Remote Similarity	NPD5778	Approved
0.6606	Remote Similarity	NPD5779	Approved
0.6604	Remote Similarity	NPD7524	Approved
0.6602	Remote Similarity	NPD6435	Approved
0.6581	Remote Similarity	NPD7320	Approved
0.6581	Remote Similarity	NPD6881	Approved
0.6581	Remote Similarity	NPD6899	Approved
0.656	Remote Similarity	NPD5988	Approved
0.6555	Remote Similarity	NPD6649	Approved
0.6555	Remote Similarity	NPD6650	Approved
0.6552	Remote Similarity	NPD6008	Approved
0.6549	Remote Similarity	NPD6648	Approved
0.6514	Remote Similarity	NPD6411	Approved
0.6508	Remote Similarity	NPD7604	Phase 2
0.6505	Remote Similarity	NPD5369	Approved
0.65	Remote Similarity	NPD6882	Approved
0.6496	Remote Similarity	NPD5701	Approved
0.6496	Remote Similarity	NPD5697	Approved
0.6486	Remote Similarity	NPD5695	Phase 3
0.6476	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD7102	Approved
0.6471	Remote Similarity	NPD7290	Approved
0.6471	Remote Similarity	NPD6883	Approved
0.6455	Remote Similarity	NPD6399	Phase 3
0.6442	Remote Similarity	NPD4269	Approved
0.6442	Remote Similarity	NPD4270	Approved
0.6423	Remote Similarity	NPD6009	Approved
0.6417	Remote Similarity	NPD6617	Approved
0.6417	Remote Similarity	NPD6869	Approved
0.6417	Remote Similarity	NPD8130	Phase 1
0.6417	Remote Similarity	NPD6847	Approved
0.6408	Remote Similarity	NPD5368	Approved
0.6387	Remote Similarity	NPD6014	Approved
0.6387	Remote Similarity	NPD6012	Approved
0.6387	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6387	Remote Similarity	NPD6013	Approved
0.6381	Remote Similarity	NPD5362	Discontinued
0.6381	Remote Similarity	NPD6695	Phase 3
0.6381	Remote Similarity	NPD7154	Phase 3
0.6378	Remote Similarity	NPD8328	Phase 3
0.6355	Remote Similarity	NPD7334	Approved
0.6355	Remote Similarity	NPD6409	Approved
0.6355	Remote Similarity	NPD5330	Approved
0.6355	Remote Similarity	NPD7146	Approved
0.6355	Remote Similarity	NPD6684	Approved
0.6355	Remote Similarity	NPD7521	Approved
0.6355	Remote Similarity	NPD5786	Approved
0.6349	Remote Similarity	NPD5983	Phase 2
0.6348	Remote Similarity	NPD4159	Approved
0.633	Remote Similarity	NPD6101	Approved
0.633	Remote Similarity	NPD1695	Approved
0.633	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6321	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD5696	Approved
0.6308	Remote Similarity	NPD6033	Approved
0.6303	Remote Similarity	NPD6011	Approved
0.629	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6288	Remote Similarity	NPD7260	Phase 2
0.6281	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6279	Remote Similarity	NPD6336	Discontinued
0.6279	Remote Similarity	NPD8273	Phase 1
0.6262	Remote Similarity	NPD5363	Approved
0.625	Remote Similarity	NPD4252	Approved
0.625	Remote Similarity	NPD5282	Discontinued
0.6239	Remote Similarity	NPD6903	Approved
0.6239	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6228	Remote Similarity	NPD4755	Approved
0.6226	Remote Similarity	NPD5332	Approved
0.6226	Remote Similarity	NPD5331	Approved
0.622	Remote Similarity	NPD6921	Approved
0.6216	Remote Similarity	NPD5693	Phase 1
0.6214	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6195	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6195	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.619	Remote Similarity	NPD4790	Discontinued
0.6182	Remote Similarity	NPD4753	Phase 2
0.6168	Remote Similarity	NPD3133	Approved
0.6168	Remote Similarity	NPD3665	Phase 1
0.6168	Remote Similarity	NPD3666	Approved
0.6161	Remote Similarity	NPD4202	Approved
0.6154	Remote Similarity	NPD5211	Phase 2
0.6147	Remote Similarity	NPD7750	Discontinued
0.6147	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.614	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.614	Remote Similarity	NPD7839	Suspended
0.6132	Remote Similarity	NPD5209	Approved
0.6124	Remote Similarity	NPD7830	Approved
0.6124	Remote Similarity	NPD6067	Discontinued
0.6124	Remote Similarity	NPD7829	Approved
0.6121	Remote Similarity	NPD4696	Approved
0.6121	Remote Similarity	NPD5285	Approved
0.6121	Remote Similarity	NPD5286	Approved
0.6121	Remote Similarity	NPD4700	Approved
0.6111	Remote Similarity	NPD1694	Approved
0.6111	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6095	Remote Similarity	NPD7525	Registered
0.6095	Remote Similarity	NPD6931	Approved
0.6095	Remote Similarity	NPD6930	Phase 2
0.609	Remote Similarity	NPD5956	Approved
0.6083	Remote Similarity	NPD6685	Approved
0.608	Remote Similarity	NPD6274	Approved
0.6071	Remote Similarity	NPD5284	Approved
0.6071	Remote Similarity	NPD5281	Approved
0.6063	Remote Similarity	NPD7100	Approved
0.6063	Remote Similarity	NPD7101	Approved
0.6063	Remote Similarity	NPD4522	Approved
0.6055	Remote Similarity	NPD6098	Approved
0.605	Remote Similarity	NPD5141	Approved
0.6036	Remote Similarity	NPD6904	Approved
0.6036	Remote Similarity	NPD6673	Approved
0.6036	Remote Similarity	NPD6080	Approved
0.6031	Remote Similarity	NPD8451	Approved
0.6019	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6019	Remote Similarity	NPD4786	Approved
0.6019	Remote Similarity	NPD6933	Approved
0.6017	Remote Similarity	NPD5225	Approved
0.6017	Remote Similarity	NPD5226	Approved
0.6017	Remote Similarity	NPD4633	Approved
0.6017	Remote Similarity	NPD5224	Approved
0.6	Remote Similarity	NPD6845	Suspended
0.6	Remote Similarity	NPD4768	Approved
0.6	Remote Similarity	NPD7642	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