NPASS Compound

Structure

NPC474783 OpenBabel07101718302D 34 37 0 0 1 0 0 0 0 0999 V2000 3.9831 -3.4400 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4582 -0.7384 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3945 -3.7127 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9981 2.7546 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9593 1.8380 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9831 -2.4682 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1414 -1.9823 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1414 -1.0105 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2998 -0.5246 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0105 -0.6024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0105 0.7972 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6904 -1.1586 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4217 -0.8756 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6166 -0.2525 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8162 -2.8372 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5375 1.8989 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6166 0.4473 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.5955 -0.2525 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.2998 0.4473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5273 0.1384 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.1056 1.0140 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.8249 -0.5331 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.1426 0.8836 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.5955 0.4473 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.9691 -0.0726 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.7853 -2.7645 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.0484 1.0722 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.1414 0.9332 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4835 -0.0351 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2687 -2.0342 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 -2.5662 1.8698 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4582 0.9332 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.1426 -0.6889 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 6 1 0 0 0 0 2 14 1 0 0 0 0 3 15 1 0 0 0 0 4 16 1 0 0 0 0 5 23 1 0 0 0 0 6 7 1 0 0 0 0 7 8 1 0 0 0 0 8 9 1 0 0 0 0 9 19 1 0 0 0 0 10 14 2 0 0 0 0 10 18 1 0 0 0 0 11 17 1 0 0 0 0 11 24 1 0 0 0 0 12 30 1 0 0 0 0 13 25 1 0 0 0 0 13 31 1 0 0 0 0 14 17 1 0 0 0 0 15 26 2 0 0 0 0 15 30 1 0 0 0 0 16 27 2 0 0 0 0 16 32 1 0 0 0 0 17 33 1 6 0 0 0 18 24 1 1 0 0 0 18 34 1 0 0 0 0 19 28 2 0 0 0 0 19 33 1 0 0 0 0 20 21 1 0 0 0 0 20 22 1 0 0 0 0 20 29 1 6 0 0 0 21 23 1 1 0 0 0 21 32 1 0 0 0 0 22 25 1 1 0 0 0 22 34 1 0 0 0 0 23 24 1 6 0 0 0 24 12 1 6 0 0 0 25 23 1 1 0 0 0 25 31 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	480.24
Volume:	475.296
LogP:	2.91
LogD:	1.996
LogS:	-4.393
# Rotatable Bonds:	11
TPSA:	120.89
# H-Bond Aceptor:	9
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.183
Synthetic Accessibility Score:	5.962
Fsp3:	0.8
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:	-5.21
MDCK Permeability:	6.809744809288532e-05
Pgp-inhibitor:	0.966
Pgp-substrate:	0.996
Human Intestinal Absorption (HIA):	0.013
20% Bioavailability (F20%):	0.232
30% Bioavailability (F30%):	0.812

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.313
Plasma Protein Binding (PPB):	70.15025329589844%
Volume Distribution (VD):	1.339
Pgp-substrate:	24.114742279052734%

ADMET: Metabolism

CYP1A2-inhibitor:	0.035
CYP1A2-substrate:	0.094
CYP2C19-inhibitor:	0.064
CYP2C19-substrate:	0.53
CYP2C9-inhibitor:	0.116
CYP2C9-substrate:	0.03
CYP2D6-inhibitor:	0.034
CYP2D6-substrate:	0.067
CYP3A4-inhibitor:	0.701
CYP3A4-substrate:	0.324

ADMET: Excretion

Clearance (CL):	3.045
Half-life (T1/2):	0.792

ADMET: Toxicity

hERG Blockers:	0.133
Human Hepatotoxicity (H-HT):	0.735
Drug-inuced Liver Injury (DILI):	0.91
AMES Toxicity:	0.846
Rat Oral Acute Toxicity:	0.321
Maximum Recommended Daily Dose:	0.3
Skin Sensitization:	0.378
Carcinogencity:	0.062
Eye Corrosion:	0.004
Eye Irritation:	0.036
Respiratory Toxicity:	0.118

Download Data

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

Natural Product: NPC474783

Natural Product ID:	NPC474783
*Common Name:**	NTQOBLPQKXJXCZ-JWXHXBNGSA-N
IUPAC Name:	n.a.
Synonyms:	8-N-Hexanoylneosolaniol
Standard InCHIKey:	NTQOBLPQKXJXCZ-JWXHXBNGSA-N
Standard InCHI:	InChI=1S/C25H36O9/c1-6-7-8-9-19(28)33-17-11-24(12-30-15(3)26)18(10-14(17)2)34-22-20(29)21(32-16(4)27)23(24,5)25(22)13-31-25/h10,17-18,20-22,29H,6-9,11-13H2,1-5H3/t17-,18+,20+,21+,22+,23+,24+,25+/m0/s1
SMILES:	CCCCCC(=O)OC1CC2(C(C=C1C)OC3C(C(C2(C34CO4)C)OC(=O)C)O)COC(=O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL482606
PubChem CID:	44576030
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]
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
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT27	Others	Unspecified		LC100	=	14.0	ng/ml	PMID[544926]

☑ 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 NPC474783 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	1180
0.2-0.3	4569
0.3-0.4	11593
0.4-0.5	10841
0.5-0.6	6792
0.6-0.7	6338
0.7-0.8	1107
0.8-0.85	21
0.85-0.9	41
0.9-0.95	7
0.95-1	13

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC260809
0.9895	High Similarity	NPC475956
0.9895	High Similarity	NPC252242
0.9789	High Similarity	NPC26557
0.9688	High Similarity	NPC200672
0.9688	High Similarity	NPC214714
0.9588	High Similarity	NPC232515
0.9579	High Similarity	NPC79449
0.9579	High Similarity	NPC474957
0.9485	High Similarity	NPC475986
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
0.9029	High Similarity	NPC50223
0.8889	High Similarity	NPC79631
0.8868	High Similarity	NPC305044
0.8868	High Similarity	NPC265290
0.8857	High Similarity	NPC98038
0.8857	High Similarity	NPC313921
0.8846	High Similarity	NPC41551
0.8824	High Similarity	NPC93026
0.8824	High Similarity	NPC469960
0.8824	High Similarity	NPC265502
0.8824	High Similarity	NPC29389
0.8774	High Similarity	NPC101965
0.8774	High Similarity	NPC101400
0.8738	High Similarity	NPC469959
0.8738	High Similarity	NPC469957
0.8738	High Similarity	NPC108682
0.8738	High Similarity	NPC472263
0.8646	High Similarity	NPC197107
0.8624	High Similarity	NPC475130
0.8624	High Similarity	NPC474286
0.8447	Intermediate Similarity	NPC123505
0.8365	Intermediate Similarity	NPC169843
0.8333	Intermediate Similarity	NPC98813
0.8333	Intermediate Similarity	NPC13743
0.8257	Intermediate Similarity	NPC287075
0.8235	Intermediate Similarity	NPC65700
0.8224	Intermediate Similarity	NPC77089
0.8165	Intermediate Similarity	NPC126691
0.8113	Intermediate Similarity	NPC470980
0.8113	Intermediate Similarity	NPC475290
0.8058	Intermediate Similarity	NPC222303
0.8019	Intermediate Similarity	NPC475585
0.8019	Intermediate Similarity	NPC474550
0.8019	Intermediate Similarity	NPC473577
0.7982	Intermediate Similarity	NPC79579
0.7982	Intermediate Similarity	NPC472215
0.7982	Intermediate Similarity	NPC472214
0.7944	Intermediate Similarity	NPC60315
0.7925	Intermediate Similarity	NPC474775
0.7909	Intermediate Similarity	NPC71680
0.7909	Intermediate Similarity	NPC474750
0.7895	Intermediate Similarity	NPC5292
0.789	Intermediate Similarity	NPC472216
0.789	Intermediate Similarity	NPC5475
0.789	Intermediate Similarity	NPC284828
0.789	Intermediate Similarity	NPC173905
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
0.7857	Intermediate Similarity	NPC178289
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	NPC241477
0.783	Intermediate Similarity	NPC470972
0.7818	Intermediate Similarity	NPC15551
0.781	Intermediate Similarity	NPC167974
0.7807	Intermediate Similarity	NPC153440
0.7807	Intermediate Similarity	NPC475401
0.7798	Intermediate Similarity	NPC55972
0.7798	Intermediate Similarity	NPC14862
0.7798	Intermediate Similarity	NPC233379
0.7798	Intermediate Similarity	NPC327286
0.7798	Intermediate Similarity	NPC169888
0.7798	Intermediate Similarity	NPC88701
0.7798	Intermediate Similarity	NPC474664
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	NPC4620
0.7757	Intermediate Similarity	NPC473694
0.7757	Intermediate Similarity	NPC473523
0.7757	Intermediate Similarity	NPC474165
0.7739	Intermediate Similarity	NPC305260
0.7739	Intermediate Similarity	NPC270850
0.7739	Intermediate Similarity	NPC477092
0.7736	Intermediate Similarity	NPC475617
0.7727	Intermediate Similarity	NPC187876
0.7727	Intermediate Similarity	NPC475922
0.7727	Intermediate Similarity	NPC15218
0.7719	Intermediate Similarity	NPC475305
0.7706	Intermediate Similarity	NPC144459
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	NPC475676
0.7685	Intermediate Similarity	NPC470104
0.7685	Intermediate Similarity	NPC220964
0.7685	Intermediate Similarity	NPC473543
0.7685	Intermediate Similarity	NPC258532
0.7679	Intermediate Similarity	NPC317687
0.7677	Intermediate Similarity	NPC137253
0.7677	Intermediate Similarity	NPC477668
0.7672	Intermediate Similarity	NPC472004
0.7672	Intermediate Similarity	NPC474585
0.7664	Intermediate Similarity	NPC183571
0.7664	Intermediate Similarity	NPC476471
0.7664	Intermediate Similarity	NPC475344
0.7664	Intermediate Similarity	NPC472552
0.7664	Intermediate Similarity	NPC473928
0.7658	Intermediate Similarity	NPC475563
0.7658	Intermediate Similarity	NPC161816
0.7658	Intermediate Similarity	NPC475134
0.7658	Intermediate Similarity	NPC115257
0.7642	Intermediate Similarity	NPC230546
0.7636	Intermediate Similarity	NPC10150
0.7636	Intermediate Similarity	NPC472439
0.7636	Intermediate Similarity	NPC472218
0.7636	Intermediate Similarity	NPC472219
0.7636	Intermediate Similarity	NPC472217
0.7636	Intermediate Similarity	NPC469916
0.7636	Intermediate Similarity	NPC472825
0.7636	Intermediate Similarity	NPC94377
0.7632	Intermediate Similarity	NPC190286
0.7632	Intermediate Similarity	NPC277583
0.7632	Intermediate Similarity	NPC106228
0.7632	Intermediate Similarity	NPC138372
0.7627	Intermediate Similarity	NPC6193
0.7627	Intermediate Similarity	NPC27363
0.7619	Intermediate Similarity	NPC210337
0.7619	Intermediate Similarity	NPC472290
0.7615	Intermediate Similarity	NPC54737
0.7615	Intermediate Similarity	NPC475802
0.7611	Intermediate Similarity	NPC317210
0.7611	Intermediate Similarity	NPC962
0.7611	Intermediate Similarity	NPC250109
0.7607	Intermediate Similarity	NPC46570
0.7607	Intermediate Similarity	NPC310511
0.7607	Intermediate Similarity	NPC67569
0.7596	Intermediate Similarity	NPC20546
0.7593	Intermediate Similarity	NPC475321
0.7589	Intermediate Similarity	NPC317107
0.7589	Intermediate Similarity	NPC475480
0.7589	Intermediate Similarity	NPC473921
0.7589	Intermediate Similarity	NPC475668
0.7586	Intermediate Similarity	NPC19028
0.7586	Intermediate Similarity	NPC472667
0.7586	Intermediate Similarity	NPC475041
0.7586	Intermediate Similarity	NPC9674
0.7586	Intermediate Similarity	NPC477071
0.7586	Intermediate Similarity	NPC278681
0.7573	Intermediate Similarity	NPC320089
0.757	Intermediate Similarity	NPC150923
0.757	Intermediate Similarity	NPC472554
0.757	Intermediate Similarity	NPC280991
0.757	Intermediate Similarity	NPC11974
0.7568	Intermediate Similarity	NPC139838
0.7568	Intermediate Similarity	NPC59489
0.7565	Intermediate Similarity	NPC203862
0.7565	Intermediate Similarity	NPC290693
0.7565	Intermediate Similarity	NPC473590
0.7563	Intermediate Similarity	NPC8374
0.7551	Intermediate Similarity	NPC231601
0.7545	Intermediate Similarity	NPC67321
0.7545	Intermediate Similarity	NPC471601
0.7545	Intermediate Similarity	NPC187435
0.7545	Intermediate Similarity	NPC475781
0.7544	Intermediate Similarity	NPC106446
0.7544	Intermediate Similarity	NPC220293
0.7544	Intermediate Similarity	NPC43213
0.7542	Intermediate Similarity	NPC269642
0.7542	Intermediate Similarity	NPC115349
0.7541	Intermediate Similarity	NPC173347
0.7524	Intermediate Similarity	NPC88009
0.7524	Intermediate Similarity	NPC476315
0.7524	Intermediate Similarity	NPC57664
0.7523	Intermediate Similarity	NPC473175
0.7523	Intermediate Similarity	NPC146731
0.7523	Intermediate Similarity	NPC296950
0.7522	Intermediate Similarity	NPC236217

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 NPC474783 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	1512
0.2-0.3	3966
0.3-0.4	2419
0.4-0.5	623
0.5-0.6	250
0.6-0.7	211
0.7-0.8	12
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
0.79	Intermediate Similarity	NPD6698	Approved
0.79	Intermediate Similarity	NPD46	Approved
0.7547	Intermediate Similarity	NPD7638	Approved
0.75	Intermediate Similarity	NPD7507	Approved
0.7477	Intermediate Similarity	NPD7640	Approved
0.7477	Intermediate Similarity	NPD7639	Approved
0.7477	Intermediate Similarity	NPD6686	Approved
0.7411	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7387	Intermediate Similarity	NPD6412	Phase 2
0.7368	Intermediate Similarity	NPD6053	Discontinued
0.735	Intermediate Similarity	NPD7328	Approved
0.735	Intermediate Similarity	NPD7327	Approved
0.7345	Intermediate Similarity	NPD6371	Approved
0.7317	Intermediate Similarity	NPD7319	Approved
0.7311	Intermediate Similarity	NPD8033	Approved
0.7311	Intermediate Similarity	NPD7503	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	NPD8377	Approved
0.7227	Intermediate Similarity	NPD6319	Approved
0.7227	Intermediate Similarity	NPD8294	Approved
0.7212	Intermediate Similarity	NPD7838	Discovery
0.7193	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7167	Intermediate Similarity	NPD8296	Approved
0.7167	Intermediate Similarity	NPD8380	Approved
0.7167	Intermediate Similarity	NPD8335	Approved
0.7167	Intermediate Similarity	NPD8379	Approved
0.7167	Intermediate Similarity	NPD8378	Approved
0.7087	Intermediate Similarity	NPD4250	Approved
0.7087	Intermediate Similarity	NPD4251	Approved
0.7071	Intermediate Similarity	NPD4820	Approved
0.7071	Intermediate Similarity	NPD4819	Approved
0.7071	Intermediate Similarity	NPD5790	Clinical (unspecified phase)
0.7071	Intermediate Similarity	NPD4822	Approved
0.7071	Intermediate Similarity	NPD4821	Approved
0.7069	Intermediate Similarity	NPD8297	Approved
0.7009	Intermediate Similarity	NPD4632	Approved
0.7009	Intermediate Similarity	NPD8133	Approved
0.6991	Remote Similarity	NPD7128	Approved
0.6991	Remote Similarity	NPD6675	Approved
0.6991	Remote Similarity	NPD6402	Approved
0.6991	Remote Similarity	NPD5739	Approved
0.699	Remote Similarity	NPD4249	Approved
0.6983	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6972	Remote Similarity	NPD6084	Phase 2
0.6972	Remote Similarity	NPD6083	Phase 2
0.6957	Remote Similarity	NPD6372	Approved
0.6957	Remote Similarity	NPD6373	Approved
0.6937	Remote Similarity	NPD5344	Discontinued
0.6931	Remote Similarity	NPD6435	Approved
0.693	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6893	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6885	Remote Similarity	NPD8516	Approved
0.6885	Remote Similarity	NPD8513	Phase 3
0.6885	Remote Similarity	NPD8515	Approved
0.6885	Remote Similarity	NPD8517	Approved
0.6875	Remote Similarity	NPD7632	Discontinued
0.687	Remote Similarity	NPD6899	Approved
0.687	Remote Similarity	NPD6881	Approved
0.687	Remote Similarity	NPD7320	Approved
0.6869	Remote Similarity	NPD4271	Approved
0.6869	Remote Similarity	NPD4268	Approved
0.6855	Remote Similarity	NPD7492	Approved
0.6842	Remote Similarity	NPD6008	Approved
0.6838	Remote Similarity	NPD6650	Approved
0.6838	Remote Similarity	NPD6649	Approved
0.6822	Remote Similarity	NPD7983	Approved
0.6803	Remote Similarity	NPD6059	Approved
0.6803	Remote Similarity	NPD6054	Approved
0.68	Remote Similarity	NPD6616	Approved
0.6792	Remote Similarity	NPD6051	Approved
0.6789	Remote Similarity	NPD5695	Phase 3
0.6783	Remote Similarity	NPD5697	Approved
0.6783	Remote Similarity	NPD5701	Approved
0.678	Remote Similarity	NPD6882	Approved
0.6774	Remote Similarity	NPD7604	Phase 2
0.6759	Remote Similarity	NPD6399	Phase 3
0.6757	Remote Similarity	NPD4225	Approved
0.6757	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6752	Remote Similarity	NPD6883	Approved
0.6752	Remote Similarity	NPD7290	Approved
0.6752	Remote Similarity	NPD7102	Approved
0.6746	Remote Similarity	NPD8293	Discontinued
0.6746	Remote Similarity	NPD7078	Approved
0.6733	Remote Similarity	NPD5368	Approved
0.6729	Remote Similarity	NPD5785	Approved
0.6724	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6699	Remote Similarity	NPD5362	Discontinued
0.6699	Remote Similarity	NPD7154	Phase 3
0.6695	Remote Similarity	NPD6847	Approved
0.6695	Remote Similarity	NPD6617	Approved
0.6695	Remote Similarity	NPD6869	Approved
0.6695	Remote Similarity	NPD8130	Phase 1
0.6694	Remote Similarity	NPD6370	Approved
0.6694	Remote Similarity	NPD6009	Approved
0.6693	Remote Similarity	NPD7736	Approved
0.6667	Remote Similarity	NPD7521	Approved
0.6667	Remote Similarity	NPD6014	Approved
0.6667	Remote Similarity	NPD6012	Approved
0.6667	Remote Similarity	NPD7146	Approved
0.6667	Remote Similarity	NPD6013	Approved
0.6667	Remote Similarity	NPD5330	Approved
0.6667	Remote Similarity	NPD7334	Approved
0.6667	Remote Similarity	NPD6684	Approved
0.6667	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6409	Approved
0.6667	Remote Similarity	NPD7637	Suspended
0.6636	Remote Similarity	NPD1695	Approved
0.6614	Remote Similarity	NPD8074	Phase 3
0.6613	Remote Similarity	NPD6015	Approved
0.6613	Remote Similarity	NPD6016	Approved
0.6613	Remote Similarity	NPD5983	Phase 2
0.661	Remote Similarity	NPD4634	Approved
0.6607	Remote Similarity	NPD5696	Approved
0.6606	Remote Similarity	NPD5778	Approved
0.6606	Remote Similarity	NPD5779	Approved
0.6604	Remote Similarity	NPD7524	Approved
0.6581	Remote Similarity	NPD6011	Approved
0.656	Remote Similarity	NPD5988	Approved
0.6555	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6549	Remote Similarity	NPD6648	Approved
0.6542	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6542	Remote Similarity	NPD6903	Approved
0.6538	Remote Similarity	NPD7260	Phase 2
0.6535	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6535	Remote Similarity	NPD6336	Discontinued
0.6518	Remote Similarity	NPD4755	Approved
0.6514	Remote Similarity	NPD6411	Approved
0.6514	Remote Similarity	NPD5693	Phase 1
0.6505	Remote Similarity	NPD5369	Approved
0.6486	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6481	Remote Similarity	NPD4753	Phase 2
0.6476	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6476	Remote Similarity	NPD3666	Approved
0.6476	Remote Similarity	NPD3133	Approved
0.6476	Remote Similarity	NPD3665	Phase 1
0.6455	Remote Similarity	NPD4202	Approved
0.6442	Remote Similarity	NPD4270	Approved
0.6442	Remote Similarity	NPD4269	Approved
0.6435	Remote Similarity	NPD5211	Phase 2
0.6415	Remote Similarity	NPD1694	Approved
0.6415	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6404	Remote Similarity	NPD5286	Approved
0.6404	Remote Similarity	NPD4700	Approved
0.6404	Remote Similarity	NPD4696	Approved
0.6404	Remote Similarity	NPD5285	Approved
0.6381	Remote Similarity	NPD5331	Approved
0.6381	Remote Similarity	NPD5332	Approved
0.6381	Remote Similarity	NPD6695	Phase 3
0.6378	Remote Similarity	NPD6067	Discontinued
0.6378	Remote Similarity	NPD8328	Phase 3
0.6364	Remote Similarity	NPD5284	Approved
0.6364	Remote Similarity	NPD5281	Approved
0.6355	Remote Similarity	NPD6098	Approved
0.6355	Remote Similarity	NPD5786	Approved
0.6348	Remote Similarity	NPD4159	Approved
0.6346	Remote Similarity	NPD4790	Discontinued
0.6341	Remote Similarity	NPD6274	Approved
0.633	Remote Similarity	NPD6101	Approved
0.633	Remote Similarity	NPD6904	Approved
0.633	Remote Similarity	NPD6080	Approved
0.633	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.633	Remote Similarity	NPD6673	Approved
0.6325	Remote Similarity	NPD5141	Approved
0.6321	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6321	Remote Similarity	NPD4786	Approved
0.632	Remote Similarity	NPD7100	Approved
0.632	Remote Similarity	NPD7101	Approved
0.6308	Remote Similarity	NPD6033	Approved
0.6293	Remote Similarity	NPD5226	Approved
0.6293	Remote Similarity	NPD5224	Approved
0.6293	Remote Similarity	NPD4633	Approved
0.6293	Remote Similarity	NPD5225	Approved
0.629	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6286	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6286	Remote Similarity	NPD3667	Approved
0.6279	Remote Similarity	NPD8273	Phase 1
0.6271	Remote Similarity	NPD4767	Approved
0.6271	Remote Similarity	NPD4768	Approved
0.6262	Remote Similarity	NPD5363	Approved
0.625	Remote Similarity	NPD5282	Discontinued
0.625	Remote Similarity	NPD7748	Approved
0.625	Remote Similarity	NPD4252	Approved
0.6241	Remote Similarity	NPD6845	Suspended
0.624	Remote Similarity	NPD6335	Approved
0.6239	Remote Similarity	NPD5174	Approved
0.6239	Remote Similarity	NPD6672	Approved
0.6239	Remote Similarity	NPD5737	Approved
0.6239	Remote Similarity	NPD5175	Approved
0.6238	Remote Similarity	NPD8039	Approved
0.6228	Remote Similarity	NPD7902	Approved
0.622	Remote Similarity	NPD6921	Approved
0.622	Remote Similarity	NPD6909	Approved
0.622	Remote Similarity	NPD6908	Approved
0.6218	Remote Similarity	NPD6685	Approved
0.6216	Remote Similarity	NPD8034	Phase 2
0.6216	Remote Similarity	NPD7515	Phase 2
0.6216	Remote Similarity	NPD8035	Phase 2
0.6216	Remote Similarity	NPD6050	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