NPASS Compound

Structure

CID169843 OpenBabel06191715542D 24 27 0 0 1 0 0 0 0 0999 V2000 2.6062 4.5754 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9494 -1.1620 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4875 1.1533 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1058 1.7338 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9385 3.8975 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1918 2.9803 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3116 -1.1680 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5971 -0.2163 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3116 0.7352 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0355 -0.4745 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1357 -0.6922 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1357 0.2594 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4875 -0.6922 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.1841 0.6411 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.1843 -1.0738 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.5241 2.3023 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4875 0.2594 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.2564 0.8527 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.3932 -0.2680 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.9494 0.7292 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.6031 2.5416 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 0.2566 -1.2854 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7773 1.3851 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 5 1 0 0 0 0 2 11 1 0 0 0 0 3 17 1 0 0 0 0 4 18 1 0 0 0 0 5 6 2 0 0 0 0 6 16 1 0 0 0 0 7 11 2 0 0 0 0 7 13 1 0 0 0 0 8 14 1 0 0 0 0 8 15 1 0 0 0 0 9 12 1 0 0 0 0 9 17 1 0 0 0 0 10 22 1 0 0 0 0 11 12 1 0 0 0 0 12 20 2 0 0 0 0 13 17 1 6 0 0 0 13 23 1 0 0 0 0 14 18 1 6 0 0 0 14 24 1 0 0 0 0 15 19 1 6 0 0 0 15 23 1 0 0 0 0 16 21 2 0 0 0 0 16 24 1 0 0 0 0 17 18 1 6 0 0 0 18 19 1 6 0 0 0 19 10 1 1 0 0 0 19 22 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	332.16
Volume:	336.36
LogP:	2.427
LogD:	1.09
LogS:	-4.179
# Rotatable Bonds:	3
TPSA:	65.13
# H-Bond Aceptor:	5
# H-Bond Donor:	0
# Rings:	4
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.442
Synthetic Accessibility Score:	6.209
Fsp3:	0.684
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.784
MDCK Permeability:	1.3151756320439745e-05
Pgp-inhibitor:	0.961
Pgp-substrate:	0.051
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.543
30% Bioavailability (F30%):	0.368

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.943
Plasma Protein Binding (PPB):	85.08594512939453%
Volume Distribution (VD):	1.416
Pgp-substrate:	18.6862850189209%

ADMET: Metabolism

CYP1A2-inhibitor:	0.036
CYP1A2-substrate:	0.375
CYP2C19-inhibitor:	0.444
CYP2C19-substrate:	0.857
CYP2C9-inhibitor:	0.331
CYP2C9-substrate:	0.063
CYP2D6-inhibitor:	0.028
CYP2D6-substrate:	0.115
CYP3A4-inhibitor:	0.728
CYP3A4-substrate:	0.759

ADMET: Excretion

Clearance (CL):	7.542
Half-life (T1/2):	0.823

ADMET: Toxicity

hERG Blockers:	0.08
Human Hepatotoxicity (H-HT):	0.862
Drug-inuced Liver Injury (DILI):	0.304
AMES Toxicity:	0.139
Rat Oral Acute Toxicity:	0.276
Maximum Recommended Daily Dose:	0.895
Skin Sensitization:	0.905
Carcinogencity:	0.867
Eye Corrosion:	0.89
Eye Irritation:	0.388
Respiratory Toxicity:	0.881

Download Data

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

Natural Product: NPC169843

Natural Product ID:	NPC169843
*Common Name:**	Trichothecin
IUPAC Name:	n.a.
Synonyms:	Trichothecin
Standard InCHIKey:	LJWZOKOFCBPNAG-HULHSAFCSA-N
Standard InCHI:	InChI=1S/C19H24O5/c1-5-6-16(21)24-14-8-15-19(10-22-19)18(14,4)17(3)9-12(20)11(2)7-13(17)23-15/h5-7,13-15H,8-10H2,1-4H3/b6-5-/t13-,14-,15-,17+,18-,19+/m1/s1
SMILES:	C/C=CC(=O)O[C@@H]1C[C@@H]2[C@]3([C@@]1(C)[C@@]1(C)CC(=O)C(=C[C@H]1O2)C)CO3
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL480472
PubChem CID:	12444502
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
NPO12483	Holarrhena floribunda	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10650079]
NPO12483	Holarrhena floribunda	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16441070]
NPO12483	Holarrhena floribunda	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19299148]
NPO30894	Trichothecium species	Species	n.a.	Eukaryota	n.a.	n.a.	n.a.	PMID[21978324]
NPO12483	Holarrhena floribunda	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO12483	Holarrhena floribunda	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12483	Holarrhena floribunda	Species	Apocynaceae	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
EC50	4
Others	1

Activity Type	# Activity
Cell Line	4
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	EC50	=	35.0	ug.mL-1	PMID[455005]
NPT2359	Cell Line	SK-MEL-30	Homo sapiens	EC50	=	14.0	ug.mL-1	PMID[455005]
NPT81	Cell Line	A549	Homo sapiens	EC50	=	16.0	ug.mL-1	PMID[455005]
NPT83	Cell Line	MCF7	Homo sapiens	EC50	=	19.0	ug.mL-1	PMID[455005]
NPT140	Organism	Artemia	Artemia	LC50	=	2.2	ug.mL-1	PMID[455005]

☑ 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 NPC169843 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	245
0.1-0.2	1355
0.2-0.3	5168
0.3-0.4	9090
0.4-0.5	13172
0.5-0.6	7533
0.6-0.7	4986
0.7-0.8	1051
0.8-0.85	80
0.85-0.9	11
0.9-0.95	4
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9505	High Similarity	NPC41551
0.9314	High Similarity	NPC50223
0.91	High Similarity	NPC123505
0.8667	High Similarity	NPC77089
0.8614	High Similarity	NPC98813
0.8614	High Similarity	NPC79631
0.8614	High Similarity	NPC13743
0.8505	High Similarity	NPC474750
0.844	Intermediate Similarity	NPC305044
0.844	Intermediate Similarity	NPC265290
0.8426	Intermediate Similarity	NPC98038
0.8426	Intermediate Similarity	NPC313921
0.8365	Intermediate Similarity	NPC260809
0.8365	Intermediate Similarity	NPC474783
0.8349	Intermediate Similarity	NPC101400
0.8349	Intermediate Similarity	NPC101965
0.8333	Intermediate Similarity	NPC475495
0.8302	Intermediate Similarity	NPC470192
0.8269	Intermediate Similarity	NPC252242
0.8269	Intermediate Similarity	NPC475956
0.8257	Intermediate Similarity	NPC475277
0.8257	Intermediate Similarity	NPC473522
0.8257	Intermediate Similarity	NPC477093
0.8218	Intermediate Similarity	NPC240838
0.8214	Intermediate Similarity	NPC474286
0.8214	Intermediate Similarity	NPC475130
0.8208	Intermediate Similarity	NPC29389
0.8208	Intermediate Similarity	NPC469960
0.8208	Intermediate Similarity	NPC93026
0.8208	Intermediate Similarity	NPC265502
0.8173	Intermediate Similarity	NPC26557
0.8155	Intermediate Similarity	NPC474957
0.8155	Intermediate Similarity	NPC79449
0.8148	Intermediate Similarity	NPC187876
0.8131	Intermediate Similarity	NPC469959
0.8131	Intermediate Similarity	NPC108682
0.8131	Intermediate Similarity	NPC469957
0.8131	Intermediate Similarity	NPC472263
0.81	Intermediate Similarity	NPC221282
0.8095	Intermediate Similarity	NPC78127
0.8095	Intermediate Similarity	NPC214714
0.8095	Intermediate Similarity	NPC475986
0.8095	Intermediate Similarity	NPC49393
0.8095	Intermediate Similarity	NPC471757
0.8095	Intermediate Similarity	NPC200672
0.8091	Intermediate Similarity	NPC471570
0.8073	Intermediate Similarity	NPC253906
0.807	Intermediate Similarity	NPC79579
0.8058	Intermediate Similarity	NPC182811
0.8058	Intermediate Similarity	NPC347923
0.8058	Intermediate Similarity	NPC476057
0.8056	Intermediate Similarity	NPC10150
0.8053	Intermediate Similarity	NPC153440
0.8019	Intermediate Similarity	NPC232515
0.8	Intermediate Similarity	NPC310511
0.7982	Intermediate Similarity	NPC5292
0.7982	Intermediate Similarity	NPC469370
0.7981	Intermediate Similarity	NPC274458
0.7966	Intermediate Similarity	NPC287423
0.7965	Intermediate Similarity	NPC475305
0.7963	Intermediate Similarity	NPC471601
0.7959	Intermediate Similarity	NPC469676
0.7959	Intermediate Similarity	NPC261253
0.7959	Intermediate Similarity	NPC474045
0.7925	Intermediate Similarity	NPC105725
0.7913	Intermediate Similarity	NPC474585
0.79	Intermediate Similarity	NPC78008
0.7895	Intermediate Similarity	NPC470420
0.7895	Intermediate Similarity	NPC475401
0.7895	Intermediate Similarity	NPC473720
0.7879	Intermediate Similarity	NPC231889
0.7876	Intermediate Similarity	NPC190286
0.787	Intermediate Similarity	NPC291643
0.787	Intermediate Similarity	NPC54737
0.7826	Intermediate Similarity	NPC305260
0.7826	Intermediate Similarity	NPC475520
0.7826	Intermediate Similarity	NPC477092
0.7826	Intermediate Similarity	NPC270850
0.7826	Intermediate Similarity	NPC472667
0.7822	Intermediate Similarity	NPC62815
0.7822	Intermediate Similarity	NPC475748
0.7818	Intermediate Similarity	NPC471934
0.781	Intermediate Similarity	NPC470188
0.781	Intermediate Similarity	NPC65700
0.7778	Intermediate Similarity	NPC228669
0.7778	Intermediate Similarity	NPC107493
0.7778	Intermediate Similarity	NPC164835
0.7768	Intermediate Similarity	NPC126691
0.7767	Intermediate Similarity	NPC473316
0.7767	Intermediate Similarity	NPC473330
0.7759	Intermediate Similarity	NPC4548
0.7759	Intermediate Similarity	NPC143755
0.7748	Intermediate Similarity	NPC5103
0.7745	Intermediate Similarity	NPC290651
0.7736	Intermediate Similarity	NPC280963
0.7727	Intermediate Similarity	NPC472825
0.7723	Intermediate Similarity	NPC166919
0.7723	Intermediate Similarity	NPC151770
0.7719	Intermediate Similarity	NPC470793
0.7714	Intermediate Similarity	NPC47834
0.7712	Intermediate Similarity	NPC469789
0.7712	Intermediate Similarity	NPC204812
0.7699	Intermediate Similarity	NPC287075
0.7692	Intermediate Similarity	NPC46570
0.7679	Intermediate Similarity	NPC179798
0.7679	Intermediate Similarity	NPC304180
0.7672	Intermediate Similarity	NPC473203
0.7664	Intermediate Similarity	NPC471767
0.7658	Intermediate Similarity	NPC139838
0.7658	Intermediate Similarity	NPC59489
0.7647	Intermediate Similarity	NPC241456
0.7647	Intermediate Similarity	NPC81736
0.7647	Intermediate Similarity	NPC32868
0.7647	Intermediate Similarity	NPC312042
0.7647	Intermediate Similarity	NPC172154
0.7642	Intermediate Similarity	NPC222303
0.7636	Intermediate Similarity	NPC180744
0.7632	Intermediate Similarity	NPC474181
0.7627	Intermediate Similarity	NPC170538
0.7619	Intermediate Similarity	NPC477354
0.7619	Intermediate Similarity	NPC58052
0.7619	Intermediate Similarity	NPC111684
0.7615	Intermediate Similarity	NPC474741
0.7611	Intermediate Similarity	NPC236217
0.7596	Intermediate Similarity	NPC281775
0.7596	Intermediate Similarity	NPC476267
0.7593	Intermediate Similarity	NPC250594
0.7589	Intermediate Similarity	NPC15551
0.7589	Intermediate Similarity	NPC206595
0.7586	Intermediate Similarity	NPC159928
0.7583	Intermediate Similarity	NPC293112
0.7583	Intermediate Similarity	NPC473635
0.7573	Intermediate Similarity	NPC472705
0.757	Intermediate Similarity	NPC186861
0.7568	Intermediate Similarity	NPC470269
0.7565	Intermediate Similarity	NPC148458
0.7565	Intermediate Similarity	NPC176840
0.7565	Intermediate Similarity	NPC298278
0.7563	Intermediate Similarity	NPC11895
0.7547	Intermediate Similarity	NPC70145
0.7547	Intermediate Similarity	NPC91695
0.7545	Intermediate Similarity	NPC243998
0.7545	Intermediate Similarity	NPC470975
0.7545	Intermediate Similarity	NPC103088
0.7545	Intermediate Similarity	NPC470979
0.7545	Intermediate Similarity	NPC223450
0.7544	Intermediate Similarity	NPC469454
0.7544	Intermediate Similarity	NPC317210
0.7544	Intermediate Similarity	NPC469496
0.7544	Intermediate Similarity	NPC469463
0.7544	Intermediate Similarity	NPC56448
0.7542	Intermediate Similarity	NPC472001
0.7542	Intermediate Similarity	NPC67569
0.7542	Intermediate Similarity	NPC204731
0.7542	Intermediate Similarity	NPC472000
0.7542	Intermediate Similarity	NPC471999
0.7541	Intermediate Similarity	NPC470880
0.7541	Intermediate Similarity	NPC175186
0.7525	Intermediate Similarity	NPC475703
0.7524	Intermediate Similarity	NPC270013
0.7524	Intermediate Similarity	NPC14961
0.7524	Intermediate Similarity	NPC224689
0.7524	Intermediate Similarity	NPC214694
0.7523	Intermediate Similarity	NPC470954
0.7523	Intermediate Similarity	NPC474775
0.7523	Intermediate Similarity	NPC110989
0.7522	Intermediate Similarity	NPC71680
0.7522	Intermediate Similarity	NPC470960
0.7521	Intermediate Similarity	NPC475041
0.7521	Intermediate Similarity	NPC473253
0.7521	Intermediate Similarity	NPC476960
0.7521	Intermediate Similarity	NPC61520
0.75	Intermediate Similarity	NPC475657
0.75	Intermediate Similarity	NPC239273
0.75	Intermediate Similarity	NPC212486
0.75	Intermediate Similarity	NPC202824
0.75	Intermediate Similarity	NPC116139
0.75	Intermediate Similarity	NPC477950
0.75	Intermediate Similarity	NPC155873
0.75	Intermediate Similarity	NPC8369
0.75	Intermediate Similarity	NPC474547
0.75	Intermediate Similarity	NPC469684
0.75	Intermediate Similarity	NPC150923
0.75	Intermediate Similarity	NPC8374
0.75	Intermediate Similarity	NPC477361
0.75	Intermediate Similarity	NPC475099
0.75	Intermediate Similarity	NPC171759
0.748	Intermediate Similarity	NPC471170
0.748	Intermediate Similarity	NPC213634
0.7479	Intermediate Similarity	NPC470419
0.7479	Intermediate Similarity	NPC470265
0.7479	Intermediate Similarity	NPC23786
0.7478	Intermediate Similarity	NPC238667
0.7478	Intermediate Similarity	NPC178289
0.7478	Intermediate Similarity	NPC471398
0.7477	Intermediate Similarity	NPC187761
0.7477	Intermediate Similarity	NPC255592
0.7477	Intermediate Similarity	NPC177232
0.7477	Intermediate Similarity	NPC261377
0.7477	Intermediate Similarity	NPC208233

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 NPC169843 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	208
0.1-0.2	1671
0.2-0.3	4022
0.3-0.4	2142
0.4-0.5	685
0.5-0.6	211
0.6-0.7	197
0.7-0.8	14
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
0.7706	Intermediate Similarity	NPD6008	Approved
0.7327	Intermediate Similarity	NPD1733	Clinical (unspecified phase)
0.7327	Intermediate Similarity	NPD1694	Approved
0.7311	Intermediate Similarity	NPD6319	Approved
0.7304	Intermediate Similarity	NPD6053	Discontinued
0.7281	Intermediate Similarity	NPD6371	Approved
0.7241	Intermediate Similarity	NPD4632	Approved
0.7212	Intermediate Similarity	NPD1695	Approved
0.7203	Intermediate Similarity	NPD7115	Discovery
0.7168	Intermediate Similarity	NPD5697	Approved
0.7168	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.7155	Intermediate Similarity	NPD8297	Approved
0.7143	Intermediate Similarity	NPD6698	Approved
0.7143	Intermediate Similarity	NPD46	Approved
0.7105	Intermediate Similarity	NPD6881	Approved
0.7105	Intermediate Similarity	NPD6899	Approved
0.7087	Intermediate Similarity	NPD5330	Approved
0.7087	Intermediate Similarity	NPD6684	Approved
0.7087	Intermediate Similarity	NPD7334	Approved
0.7087	Intermediate Similarity	NPD7146	Approved
0.7087	Intermediate Similarity	NPD6409	Approved
0.7087	Intermediate Similarity	NPD7521	Approved
0.7075	Intermediate Similarity	NPD5693	Phase 1
0.7073	Intermediate Similarity	NPD7492	Approved
0.7069	Intermediate Similarity	NPD6650	Approved
0.7069	Intermediate Similarity	NPD6649	Approved
0.7059	Intermediate Similarity	NPD6009	Approved
0.7043	Intermediate Similarity	NPD6013	Approved
0.7043	Intermediate Similarity	NPD6014	Approved
0.7043	Intermediate Similarity	NPD6012	Approved
0.7025	Intermediate Similarity	NPD6054	Approved
0.7018	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD6412	Phase 2
0.7016	Intermediate Similarity	NPD6616	Approved
0.7016	Intermediate Similarity	NPD7507	Approved
0.6992	Remote Similarity	NPD7604	Phase 2
0.6983	Remote Similarity	NPD7290	Approved
0.6983	Remote Similarity	NPD6883	Approved
0.6983	Remote Similarity	NPD7102	Approved
0.6983	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD5785	Approved
0.6967	Remote Similarity	NPD6015	Approved
0.6967	Remote Similarity	NPD6016	Approved
0.6967	Remote Similarity	NPD5983	Phase 2
0.696	Remote Similarity	NPD7078	Approved
0.6957	Remote Similarity	NPD6011	Approved
0.6957	Remote Similarity	NPD6686	Approved
0.6952	Remote Similarity	NPD6903	Approved
0.6952	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.693	Remote Similarity	NPD6402	Approved
0.693	Remote Similarity	NPD7128	Approved
0.693	Remote Similarity	NPD6675	Approved
0.693	Remote Similarity	NPD5739	Approved
0.6923	Remote Similarity	NPD6617	Approved
0.6923	Remote Similarity	NPD6847	Approved
0.6923	Remote Similarity	NPD8130	Phase 1
0.6923	Remote Similarity	NPD6869	Approved
0.6911	Remote Similarity	NPD6370	Approved
0.6911	Remote Similarity	NPD5988	Approved
0.6905	Remote Similarity	NPD7736	Approved
0.6897	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD6372	Approved
0.6897	Remote Similarity	NPD6373	Approved
0.6881	Remote Similarity	NPD5695	Phase 3
0.6881	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6881	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD7260	Phase 2
0.687	Remote Similarity	NPD5701	Approved
0.6864	Remote Similarity	NPD6882	Approved
0.6863	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6863	Remote Similarity	NPD6435	Approved
0.685	Remote Similarity	NPD7319	Approved
0.6847	Remote Similarity	NPD7638	Approved
0.6847	Remote Similarity	NPD5696	Approved
0.6838	Remote Similarity	NPD4634	Approved
0.6822	Remote Similarity	NPD5207	Approved
0.6814	Remote Similarity	NPD5211	Phase 2
0.681	Remote Similarity	NPD7320	Approved
0.6786	Remote Similarity	NPD5286	Approved
0.6786	Remote Similarity	NPD7640	Approved
0.6786	Remote Similarity	NPD7639	Approved
0.6786	Remote Similarity	NPD4696	Approved
0.6786	Remote Similarity	NPD5285	Approved
0.6759	Remote Similarity	NPD5694	Approved
0.6759	Remote Similarity	NPD5281	Approved
0.6759	Remote Similarity	NPD5284	Approved
0.6757	Remote Similarity	NPD6083	Phase 2
0.6757	Remote Similarity	NPD6084	Phase 2
0.6748	Remote Similarity	NPD6059	Approved
0.6746	Remote Similarity	NPD6336	Discontinued
0.6729	Remote Similarity	NPD6673	Approved
0.6729	Remote Similarity	NPD6080	Approved
0.6729	Remote Similarity	NPD6904	Approved
0.6699	Remote Similarity	NPD5209	Approved
0.6698	Remote Similarity	NPD3573	Approved
0.6696	Remote Similarity	NPD5141	Approved
0.6694	Remote Similarity	NPD7503	Approved
0.6693	Remote Similarity	NPD8293	Discontinued
0.6667	Remote Similarity	NPD5225	Approved
0.6667	Remote Similarity	NPD4633	Approved
0.6667	Remote Similarity	NPD5692	Phase 3
0.6667	Remote Similarity	NPD5226	Approved
0.6667	Remote Similarity	NPD5224	Approved
0.6667	Remote Similarity	NPD5368	Approved
0.6667	Remote Similarity	NPD7838	Discovery
0.6636	Remote Similarity	NPD5737	Approved
0.6636	Remote Similarity	NPD6672	Approved
0.6636	Remote Similarity	NPD5208	Approved
0.6636	Remote Similarity	NPD5282	Discontinued
0.6636	Remote Similarity	NPD6001	Approved
0.6609	Remote Similarity	NPD5174	Approved
0.6609	Remote Similarity	NPD5175	Approved
0.6607	Remote Similarity	NPD4755	Approved
0.6606	Remote Similarity	NPD6050	Approved
0.6579	Remote Similarity	NPD5223	Approved
0.6577	Remote Similarity	NPD5210	Approved
0.6577	Remote Similarity	NPD4629	Approved
0.6574	Remote Similarity	NPD6051	Approved
0.6557	Remote Similarity	NPD6274	Approved
0.6549	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6545	Remote Similarity	NPD6399	Phase 3
0.6532	Remote Similarity	NPD7101	Approved
0.6532	Remote Similarity	NPD7100	Approved
0.6525	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6509	Remote Similarity	NPD5363	Approved
0.6504	Remote Similarity	NPD6317	Approved
0.65	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6491	Remote Similarity	NPD6648	Approved
0.6491	Remote Similarity	NPD4700	Approved
0.6452	Remote Similarity	NPD7327	Approved
0.6452	Remote Similarity	NPD6314	Approved
0.6452	Remote Similarity	NPD6335	Approved
0.6452	Remote Similarity	NPD6313	Approved
0.6452	Remote Similarity	NPD7328	Approved
0.6449	Remote Similarity	NPD4249	Approved
0.6449	Remote Similarity	NPD6098	Approved
0.6449	Remote Similarity	NPD5786	Approved
0.6439	Remote Similarity	NPD6845	Suspended
0.6435	Remote Similarity	NPD5344	Discontinued
0.6429	Remote Similarity	NPD8517	Approved
0.6429	Remote Similarity	NPD8516	Approved
0.6429	Remote Similarity	NPD8513	Phase 3
0.6429	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD8033	Approved
0.6429	Remote Similarity	NPD8515	Approved
0.6422	Remote Similarity	NPD4753	Phase 2
0.6415	Remote Similarity	NPD3133	Approved
0.6415	Remote Similarity	NPD3666	Approved
0.6415	Remote Similarity	NPD3665	Phase 1
0.6404	Remote Similarity	NPD4225	Approved
0.64	Remote Similarity	NPD7516	Approved
0.6396	Remote Similarity	NPD5779	Approved
0.6396	Remote Similarity	NPD5778	Approved
0.6389	Remote Similarity	NPD4250	Approved
0.6389	Remote Similarity	NPD4251	Approved
0.6387	Remote Similarity	NPD4730	Approved
0.6387	Remote Similarity	NPD4729	Approved
0.6364	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6349	Remote Similarity	NPD8377	Approved
0.6349	Remote Similarity	NPD8294	Approved
0.6346	Remote Similarity	NPD4822	Approved
0.6346	Remote Similarity	NPD4819	Approved
0.6346	Remote Similarity	NPD4821	Approved
0.6346	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6346	Remote Similarity	NPD4820	Approved
0.6339	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6339	Remote Similarity	NPD7900	Approved
0.6337	Remote Similarity	NPD8039	Approved
0.6316	Remote Similarity	NPD5959	Approved
0.6306	Remote Similarity	NPD6411	Approved
0.6306	Remote Similarity	NPD6079	Approved
0.6306	Remote Similarity	NPD7983	Approved
0.6303	Remote Similarity	NPD6614	Approved
0.6299	Remote Similarity	NPD8378	Approved
0.6299	Remote Similarity	NPD8380	Approved
0.6299	Remote Similarity	NPD8296	Approved
0.6299	Remote Similarity	NPD8379	Approved
0.6299	Remote Similarity	NPD8335	Approved
0.6296	Remote Similarity	NPD5690	Phase 2
0.6288	Remote Similarity	NPD5956	Approved
0.6286	Remote Similarity	NPD5369	Approved
0.6283	Remote Similarity	NPD5654	Approved
0.6281	Remote Similarity	NPD5247	Approved
0.6281	Remote Similarity	NPD5249	Phase 3
0.6281	Remote Similarity	NPD5251	Approved
0.6281	Remote Similarity	NPD5250	Approved
0.6281	Remote Similarity	NPD5248	Approved
0.626	Remote Similarity	NPD6033	Approved
0.625	Remote Similarity	NPD5128	Approved
0.625	Remote Similarity	NPD4202	Approved
0.625	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6239	Remote Similarity	NPD7632	Discontinued
0.623	Remote Similarity	NPD5217	Approved
0.623	Remote Similarity	NPD5215	Approved
0.623	Remote Similarity	NPD5216	Approved
0.6228	Remote Similarity	NPD5222	Approved
0.6228	Remote Similarity	NPD5221	Approved
0.6228	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6226	Remote Similarity	NPD4223	Phase 3
0.6226	Remote Similarity	NPD4269	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