NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	478.16
Volume:	452.203
LogP:	0.711
LogD:	0.576
LogS:	-2.829
# Rotatable Bonds:	10
TPSA:	155.38
# H-Bond Aceptor:	12
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	12

MedChem Properties

QED Drug-Likeness Score:	0.486
Synthetic Accessibility Score:	3.876
Fsp3:	0.455
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.962
MDCK Permeability:	4.081885708728805e-05
Pgp-inhibitor:	0.037
Pgp-substrate:	0.016
Human Intestinal Absorption (HIA):	0.941
20% Bioavailability (F20%):	0.088
30% Bioavailability (F30%):	0.99

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.696
Plasma Protein Binding (PPB):	30.868690490722656%
Volume Distribution (VD):	0.418
Pgp-substrate:	45.69246292114258%

ADMET: Metabolism

CYP1A2-inhibitor:	0.035
CYP1A2-substrate:	0.108
CYP2C19-inhibitor:	0.038
CYP2C19-substrate:	0.065
CYP2C9-inhibitor:	0.021
CYP2C9-substrate:	0.147
CYP2D6-inhibitor:	0.41
CYP2D6-substrate:	0.152
CYP3A4-inhibitor:	0.174
CYP3A4-substrate:	0.201

ADMET: Excretion

Clearance (CL):	7.201
Half-life (T1/2):	0.862

ADMET: Toxicity

hERG Blockers:	0.055
Human Hepatotoxicity (H-HT):	0.966
Drug-inuced Liver Injury (DILI):	0.984
AMES Toxicity:	0.217
Rat Oral Acute Toxicity:	0.022
Maximum Recommended Daily Dose:	0.022
Skin Sensitization:	0.035
Carcinogencity:	0.326
Eye Corrosion:	0.003
Eye Irritation:	0.01
Respiratory Toxicity:	0.027

Download Data

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

Natural Product: NPC476661

Natural Product ID:	NPC476661
*Common Name:**	[(2R,3R,4S,5S)-4-acetyloxy-5-[(2,4-dioxopyrimidin-1-yl)methyl]-2-(hydroxymethyl)oxolan-3-yl] 2,4-dimethoxy-6-methylbenzoate
IUPAC Name:	[(2R,3R,4S,5S)-4-acetyloxy-5-[(2,4-dioxopyrimidin-1-yl)methyl]-2-(hydroxymethyl)oxolan-3-yl] 2,4-dimethoxy-6-methylbenzoate
Synonyms:
Standard InCHIKey:	ZTGGVKXNOBHWBN-ACZWYYKOSA-N
Standard InCHI:	InChI=1S/C22H26N2O10/c1-11-7-13(30-3)8-14(31-4)18(11)21(28)34-20-16(10-25)33-15(19(20)32-12(2)26)9-24-6-5-17(27)23-22(24)29/h5-8,15-16,19-20,25H,9-10H2,1-4H3,(H,23,27,29)/t15-,16+,19-,20+/m0/s1
SMILES:	CC1=CC(=CC(=C1C(=O)O[C@@H]2[C@H](O[C@H]([C@@H]2OC(=O)C)CN3C=CC(=O)NC3=O)CO)OC)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	44445674
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0000011] Carbohydrates and carbohydrate conjugates [CHEMONTID:0002105] Glycosyl compounds [CHEMONTID:0002204] C-glycosyl compounds

*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
NPO15067	Aspergillus versicolor	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12542346]
NPO15067	Aspergillus versicolor	Species	Aspergillaceae	Eukaryota	marine sponge Xestospongia exigua	n.a.	n.a.	PMID[12542346]
NPO15067	Aspergillus versicolor	Species	Aspergillaceae	Eukaryota	isolated from the surface of a basidioma of Gandoderma australe found growing on a living tree in a montane mesic forest	Kipuka Pauula (Bird Park), Volcanoes National Park, Hawaii	n.a.	PMID[17608440]
NPO15067	Aspergillus versicolor	Species	Aspergillaceae	Eukaryota	n.a.	Australian	n.a.	PMID[19245260]
NPO15067	Aspergillus versicolor	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31390200]
NPO15067	Aspergillus versicolor	Species	Aspergillaceae	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
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	IZ	=	18	mm	PMID[17608440]

☑ 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 NPC476661 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	434
0.1-0.2	2124
0.2-0.3	8493
0.3-0.4	9319
0.4-0.5	9967
0.5-0.6	11353
0.6-0.7	973
0.7-0.8	32
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9944	High Similarity	NPC476662
0.798	Intermediate Similarity	NPC286135
0.7895	Intermediate Similarity	NPC477816
0.7833	Intermediate Similarity	NPC240768
0.7833	Intermediate Similarity	NPC200773
0.7789	Intermediate Similarity	NPC309692
0.7778	Intermediate Similarity	NPC83019
0.7772	Intermediate Similarity	NPC18306
0.7735	Intermediate Similarity	NPC215921
0.7735	Intermediate Similarity	NPC70016
0.7727	Intermediate Similarity	NPC204580
0.7672	Intermediate Similarity	NPC129578
0.7659	Intermediate Similarity	NPC293347
0.764	Intermediate Similarity	NPC210425
0.764	Intermediate Similarity	NPC280404
0.764	Intermediate Similarity	NPC277426
0.764	Intermediate Similarity	NPC86373
0.7617	Intermediate Similarity	NPC473562
0.7602	Intermediate Similarity	NPC469437
0.7598	Intermediate Similarity	NPC80472
0.7582	Intermediate Similarity	NPC469670
0.7582	Intermediate Similarity	NPC469619
0.7562	Intermediate Similarity	NPC313453
0.7561	Intermediate Similarity	NPC79130
0.7528	Intermediate Similarity	NPC474385
0.7527	Intermediate Similarity	NPC77679
0.7527	Intermediate Similarity	NPC84935
0.7527	Intermediate Similarity	NPC190020
0.7514	Intermediate Similarity	NPC210320
0.7513	Intermediate Similarity	NPC329816
0.7512	Intermediate Similarity	NPC314946
0.7512	Intermediate Similarity	NPC475768
0.7487	Intermediate Similarity	NPC279732
0.7487	Intermediate Similarity	NPC94499
0.7486	Intermediate Similarity	NPC179178
0.7486	Intermediate Similarity	NPC51106
0.7473	Intermediate Similarity	NPC73411
0.7473	Intermediate Similarity	NPC215711
0.7473	Intermediate Similarity	NPC150227
0.7472	Intermediate Similarity	NPC158634
0.7433	Intermediate Similarity	NPC246466
0.7432	Intermediate Similarity	NPC476684
0.7432	Intermediate Similarity	NPC237440
0.7432	Intermediate Similarity	NPC270160
0.743	Intermediate Similarity	NPC469579
0.7427	Intermediate Similarity	NPC246303
0.7419	Intermediate Similarity	NPC16082
0.7419	Intermediate Similarity	NPC99381
0.7419	Intermediate Similarity	NPC82592
0.7419	Intermediate Similarity	NPC69043
0.7419	Intermediate Similarity	NPC5674
0.7419	Intermediate Similarity	NPC478230
0.7419	Intermediate Similarity	NPC199926
0.7419	Intermediate Similarity	NPC79998
0.7418	Intermediate Similarity	NPC472036
0.7416	Intermediate Similarity	NPC158472
0.7405	Intermediate Similarity	NPC478224
0.7391	Intermediate Similarity	NPC96501
0.7389	Intermediate Similarity	NPC469542
0.7385	Intermediate Similarity	NPC470847
0.7377	Intermediate Similarity	NPC471641
0.7377	Intermediate Similarity	NPC240253
0.7377	Intermediate Similarity	NPC471642
0.7377	Intermediate Similarity	NPC240622
0.7374	Intermediate Similarity	NPC1704
0.7374	Intermediate Similarity	NPC67650
0.7374	Intermediate Similarity	NPC90411
0.7374	Intermediate Similarity	NPC475730
0.7366	Intermediate Similarity	NPC2173
0.7366	Intermediate Similarity	NPC281477
0.7366	Intermediate Similarity	NPC137301
0.7366	Intermediate Similarity	NPC202771
0.7366	Intermediate Similarity	NPC119818
0.7366	Intermediate Similarity	NPC328700
0.7361	Intermediate Similarity	NPC475442
0.736	Intermediate Similarity	NPC32360
0.736	Intermediate Similarity	NPC247409
0.736	Intermediate Similarity	NPC475566
0.7358	Intermediate Similarity	NPC329992
0.7354	Intermediate Similarity	NPC472055
0.7348	Intermediate Similarity	NPC184702
0.7348	Intermediate Similarity	NPC470932
0.734	Intermediate Similarity	NPC472889
0.7327	Intermediate Similarity	NPC475624
0.7326	Intermediate Similarity	NPC472890
0.7326	Intermediate Similarity	NPC170189
0.7326	Intermediate Similarity	NPC208173
0.7317	Intermediate Similarity	NPC316164
0.7316	Intermediate Similarity	NPC117985
0.7312	Intermediate Similarity	NPC184284
0.7312	Intermediate Similarity	NPC167903
0.7312	Intermediate Similarity	NPC76041
0.7312	Intermediate Similarity	NPC115249
0.731	Intermediate Similarity	NPC206061
0.7308	Intermediate Similarity	NPC472034
0.7308	Intermediate Similarity	NPC83272
0.7306	Intermediate Similarity	NPC283041
0.7302	Intermediate Similarity	NPC470339
0.7297	Intermediate Similarity	NPC472891
0.7293	Intermediate Similarity	NPC472006
0.7292	Intermediate Similarity	NPC191930
0.7287	Intermediate Similarity	NPC227062
0.7286	Intermediate Similarity	NPC14390
0.7281	Intermediate Similarity	NPC252156
0.7281	Intermediate Similarity	NPC475292
0.7281	Intermediate Similarity	NPC475565
0.7281	Intermediate Similarity	NPC475349
0.7273	Intermediate Similarity	NPC478231
0.7268	Intermediate Similarity	NPC472033
0.7268	Intermediate Similarity	NPC107625
0.7268	Intermediate Similarity	NPC470357
0.7263	Intermediate Similarity	NPC268052
0.7263	Intermediate Similarity	NPC470358
0.726	Intermediate Similarity	NPC314987
0.7254	Intermediate Similarity	NPC20237
0.7253	Intermediate Similarity	NPC27106
0.7249	Intermediate Similarity	NPC473395
0.7249	Intermediate Similarity	NPC26353
0.7249	Intermediate Similarity	NPC478225
0.7247	Intermediate Similarity	NPC135837
0.7241	Intermediate Similarity	NPC308709
0.724	Intermediate Similarity	NPC249181
0.7238	Intermediate Similarity	NPC82913
0.7238	Intermediate Similarity	NPC297985
0.7238	Intermediate Similarity	NPC250755
0.7234	Intermediate Similarity	NPC478221
0.7234	Intermediate Similarity	NPC317585
0.7231	Intermediate Similarity	NPC221792
0.7228	Intermediate Similarity	NPC166583
0.7228	Intermediate Similarity	NPC8817
0.7228	Intermediate Similarity	NPC53362
0.7225	Intermediate Similarity	NPC35345
0.7219	Intermediate Similarity	NPC271681
0.7219	Intermediate Similarity	NPC475116
0.7216	Intermediate Similarity	NPC254053
0.7213	Intermediate Similarity	NPC312789
0.7208	Intermediate Similarity	NPC99723
0.7207	Intermediate Similarity	NPC94248
0.7207	Intermediate Similarity	NPC33144
0.7207	Intermediate Similarity	NPC478200
0.7207	Intermediate Similarity	NPC212693
0.7204	Intermediate Similarity	NPC475460
0.7204	Intermediate Similarity	NPC197125
0.7204	Intermediate Similarity	NPC56204
0.7202	Intermediate Similarity	NPC7752
0.7198	Intermediate Similarity	NPC478202
0.7196	Intermediate Similarity	NPC54928
0.7196	Intermediate Similarity	NPC472050
0.7192	Intermediate Similarity	NPC264938
0.7189	Intermediate Similarity	NPC153417
0.7189	Intermediate Similarity	NPC470359
0.7188	Intermediate Similarity	NPC474858
0.7179	Intermediate Similarity	NPC117713
0.7179	Intermediate Similarity	NPC292213
0.7175	Intermediate Similarity	NPC185031
0.7174	Intermediate Similarity	NPC85734
0.7174	Intermediate Similarity	NPC473023
0.7174	Intermediate Similarity	NPC260946
0.7174	Intermediate Similarity	NPC32058
0.7173	Intermediate Similarity	NPC200594
0.7172	Intermediate Similarity	NPC312630
0.7172	Intermediate Similarity	NPC324220
0.7171	Intermediate Similarity	NPC46744
0.7171	Intermediate Similarity	NPC215098
0.7171	Intermediate Similarity	NPC70290
0.7171	Intermediate Similarity	NPC124302
0.7171	Intermediate Similarity	NPC73020
0.7171	Intermediate Similarity	NPC14622
0.717	Intermediate Similarity	NPC92235
0.7166	Intermediate Similarity	NPC228662
0.7166	Intermediate Similarity	NPC473732
0.7158	Intermediate Similarity	NPC478226
0.7158	Intermediate Similarity	NPC66404
0.7158	Intermediate Similarity	NPC95123
0.7156	Intermediate Similarity	NPC470846
0.7151	Intermediate Similarity	NPC70380
0.7143	Intermediate Similarity	NPC257266
0.7143	Intermediate Similarity	NPC16286
0.7143	Intermediate Similarity	NPC473241
0.7143	Intermediate Similarity	NPC279218
0.7143	Intermediate Similarity	NPC108937
0.7143	Intermediate Similarity	NPC314596
0.7143	Intermediate Similarity	NPC471640
0.7143	Intermediate Similarity	NPC471644
0.7135	Intermediate Similarity	NPC96031
0.7135	Intermediate Similarity	NPC182496
0.7135	Intermediate Similarity	NPC137296
0.7135	Intermediate Similarity	NPC180905
0.7135	Intermediate Similarity	NPC202494
0.7135	Intermediate Similarity	NPC69868
0.7135	Intermediate Similarity	NPC92589
0.7135	Intermediate Similarity	NPC317544
0.7129	Intermediate Similarity	NPC169605
0.7128	Intermediate Similarity	NPC472894
0.7128	Intermediate Similarity	NPC256141
0.7128	Intermediate Similarity	NPC473094
0.7128	Intermediate Similarity	NPC295646
0.7128	Intermediate Similarity	NPC471180
0.7128	Intermediate Similarity	NPC249977
0.7128	Intermediate Similarity	NPC273483

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 NPC476661 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	242
0.1-0.2	578
0.2-0.3	981
0.3-0.4	1808
0.4-0.5	2885
0.5-0.6	2177
0.6-0.7	460
0.7-0.8	18
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7806	Intermediate Similarity	NPD3473	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD5710	Approved
0.7647	Intermediate Similarity	NPD5711	Approved
0.7565	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7562	Intermediate Similarity	NPD7565	Approved
0.7525	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7451	Intermediate Similarity	NPD6863	Phase 2
0.7366	Intermediate Similarity	NPD5006	Approved
0.7366	Intermediate Similarity	NPD5005	Approved
0.7263	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.726	Intermediate Similarity	NPD8469	Approved
0.7234	Intermediate Similarity	NPD5353	Approved
0.723	Intermediate Similarity	NPD7930	Approved
0.7225	Intermediate Similarity	NPD6973	Clinical (unspecified phase)
0.7192	Intermediate Similarity	NPD4360	Phase 2
0.7192	Intermediate Similarity	NPD4363	Phase 3
0.7171	Intermediate Similarity	NPD4420	Approved
0.7157	Intermediate Similarity	NPD4361	Phase 2
0.7157	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.715	Intermediate Similarity	NPD5242	Approved
0.7143	Intermediate Similarity	NPD7583	Approved
0.7136	Intermediate Similarity	NPD7811	Phase 3
0.7136	Intermediate Similarity	NPD7810	Phase 3
0.7127	Intermediate Similarity	NPD2654	Approved
0.712	Intermediate Similarity	NPD2534	Approved
0.712	Intermediate Similarity	NPD2533	Approved
0.712	Intermediate Similarity	NPD2532	Approved
0.7109	Intermediate Similarity	NPD7585	Approved
0.7075	Intermediate Similarity	NPD8151	Discontinued
0.7062	Intermediate Similarity	NPD7584	Approved
0.7053	Intermediate Similarity	NPD3817	Phase 2
0.7044	Intermediate Similarity	NPD3808	Clinical (unspecified phase)
0.7028	Intermediate Similarity	NPD7701	Phase 2
0.7027	Intermediate Similarity	NPD8058	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD8059	Phase 3
0.7021	Intermediate Similarity	NPD4380	Phase 2
0.7	Intermediate Similarity	NPD7819	Suspended
0.6976	Remote Similarity	NPD4466	Phase 1
0.6971	Remote Similarity	NPD8285	Discontinued
0.6967	Remote Similarity	NPD8319	Approved
0.6967	Remote Similarity	NPD8320	Phase 1
0.6963	Remote Similarity	NPD7874	Approved
0.6963	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6955	Remote Similarity	NPD8366	Approved
0.6954	Remote Similarity	NPD3818	Discontinued
0.6954	Remote Similarity	NPD7177	Discontinued
0.6947	Remote Similarity	NPD6801	Discontinued
0.6944	Remote Similarity	NPD4377	Discontinued
0.6934	Remote Similarity	NPD7999	Approved
0.6931	Remote Similarity	NPD5036	Approved
0.693	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.693	Remote Similarity	NPD7783	Phase 2
0.693	Remote Similarity	NPD7801	Approved
0.6923	Remote Similarity	NPD6232	Discontinued
0.6912	Remote Similarity	NPD6836	Approved
0.6906	Remote Similarity	NPD8491	Approved
0.6897	Remote Similarity	NPD5037	Approved
0.6897	Remote Similarity	NPD5038	Approved
0.6895	Remote Similarity	NPD6385	Approved
0.6895	Remote Similarity	NPD2541	Clinical (unspecified phase)
0.6895	Remote Similarity	NPD6386	Approved
0.6891	Remote Similarity	NPD7075	Discontinued
0.6891	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6882	Remote Similarity	NPD6799	Approved
0.6881	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6878	Remote Similarity	NPD5525	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD5402	Approved
0.6875	Remote Similarity	NPD7318	Phase 3
0.6872	Remote Similarity	NPD8162	Phase 2
0.6872	Remote Similarity	NPD6823	Phase 2
0.6872	Remote Similarity	NPD8163	Clinical (unspecified phase)
0.6859	Remote Similarity	NPD1934	Approved
0.6858	Remote Similarity	NPD8067	Phase 3
0.6839	Remote Similarity	NPD3882	Suspended
0.6834	Remote Similarity	NPD7054	Approved
0.6823	Remote Similarity	NPD2801	Approved
0.6823	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6823	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6821	Remote Similarity	NPD6746	Phase 2
0.682	Remote Similarity	NPD8461	Discontinued
0.6818	Remote Similarity	NPD7473	Discontinued
0.6816	Remote Similarity	NPD7038	Approved
0.6816	Remote Similarity	NPD7039	Approved
0.6816	Remote Similarity	NPD5030	Phase 2
0.6804	Remote Similarity	NPD5219	Approved
0.6804	Remote Similarity	NPD5218	Approved
0.68	Remote Similarity	NPD7472	Approved
0.6794	Remote Similarity	NPD7282	Approved
0.6793	Remote Similarity	NPD3655	Clinical (unspecified phase)
0.6782	Remote Similarity	NPD36	Approved
0.6782	Remote Similarity	NPD5026	Approved
0.6782	Remote Similarity	NPD5028	Approved
0.6782	Remote Similarity	NPD4954	Approved
0.6782	Remote Similarity	NPD5034	Approved
0.6782	Remote Similarity	NPD4955	Approved
0.6782	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6777	Remote Similarity	NPD6782	Approved
0.6777	Remote Similarity	NPD6777	Approved
0.6777	Remote Similarity	NPD6779	Approved
0.6777	Remote Similarity	NPD6780	Approved
0.6777	Remote Similarity	NPD6776	Approved
0.6777	Remote Similarity	NPD6778	Approved
0.6777	Remote Similarity	NPD6781	Approved
0.6772	Remote Similarity	NPD5403	Approved
0.6771	Remote Similarity	NPD6844	Discontinued
0.6771	Remote Similarity	NPD7317	Phase 3
0.6768	Remote Similarity	NPD3451	Clinical (unspecified phase)
0.6768	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6768	Remote Similarity	NPD7784	Clinical (unspecified phase)
0.6768	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6768	Remote Similarity	NPD6166	Phase 2
0.6768	Remote Similarity	NPD4575	Clinical (unspecified phase)
0.6766	Remote Similarity	NPD6797	Phase 2
0.6755	Remote Similarity	NPD3688	Clinical (unspecified phase)
0.6755	Remote Similarity	NPD3157	Approved
0.6755	Remote Similarity	NPD3158	Phase 1
0.6755	Remote Similarity	NPD3146	Approved
0.6754	Remote Similarity	NPD4678	Approved
0.6754	Remote Similarity	NPD4675	Approved
0.6754	Remote Similarity	NPD6599	Discontinued
0.6753	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6751	Remote Similarity	NPD7315	Approved
0.675	Remote Similarity	NPD5844	Phase 1
0.675	Remote Similarity	NPD6020	Phase 2
0.6748	Remote Similarity	NPD6377	Clinical (unspecified phase)
0.6746	Remote Similarity	NPD7667	Clinical (unspecified phase)
0.6733	Remote Similarity	NPD6559	Discontinued
0.6733	Remote Similarity	NPD7251	Discontinued
0.673	Remote Similarity	NPD7237	Clinical (unspecified phase)
0.6726	Remote Similarity	NPD8155	Clinical (unspecified phase)
0.6726	Remote Similarity	NPD7907	Approved
0.6718	Remote Similarity	NPD1307	Phase 2
0.6718	Remote Similarity	NPD1309	Phase 2
0.6718	Remote Similarity	NPD7975	Clinical (unspecified phase)
0.6716	Remote Similarity	NPD5441	Clinical (unspecified phase)
0.6716	Remote Similarity	NPD7074	Phase 3
0.6712	Remote Similarity	NPD4111	Phase 1
0.6712	Remote Similarity	NPD4665	Approved
0.6702	Remote Similarity	NPD2649	Approved
0.6702	Remote Similarity	NPD2651	Approved
0.6702	Remote Similarity	NPD1511	Approved
0.67	Remote Similarity	NPD7808	Phase 3
0.67	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6699	Remote Similarity	NPD1898	Discontinued
0.6699	Remote Similarity	NPD4413	Clinical (unspecified phase)
0.6685	Remote Similarity	NPD2238	Phase 2
0.6685	Remote Similarity	NPD6032	Approved
0.6684	Remote Similarity	NPD3692	Discontinued
0.6684	Remote Similarity	NPD1670	Discontinued
0.6683	Remote Similarity	NPD7296	Approved
0.6682	Remote Similarity	NPD7696	Phase 3
0.6682	Remote Similarity	NPD7497	Discontinued
0.6682	Remote Similarity	NPD7435	Discontinued
0.6682	Remote Similarity	NPD7697	Approved
0.6682	Remote Similarity	NPD7698	Approved
0.6667	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5401	Approved
0.6667	Remote Similarity	NPD7827	Phase 1
0.6667	Remote Similarity	NPD7608	Discontinued
0.6667	Remote Similarity	NPD2494	Approved
0.6667	Remote Similarity	NPD2493	Approved
0.6667	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6808	Phase 2
0.6652	Remote Similarity	NPD7047	Phase 3
0.6651	Remote Similarity	NPD7870	Phase 2
0.6651	Remote Similarity	NPD6874	Approved
0.6651	Remote Similarity	NPD7871	Phase 2
0.665	Remote Similarity	NPD5029	Approved
0.665	Remote Similarity	NPD8150	Discontinued
0.665	Remote Similarity	NPD5027	Approved
0.665	Remote Similarity	NPD5031	Approved
0.6649	Remote Similarity	NPD3686	Approved
0.6649	Remote Similarity	NPD5773	Approved
0.6649	Remote Similarity	NPD3687	Approved
0.6649	Remote Similarity	NPD4210	Discontinued
0.6649	Remote Similarity	NPD5772	Approved
0.6638	Remote Similarity	NPD7048	Phase 3
0.6635	Remote Similarity	NPD2974	Approved
0.6635	Remote Similarity	NPD2973	Approved
0.6635	Remote Similarity	NPD2975	Approved
0.6632	Remote Similarity	NPD5889	Approved
0.6632	Remote Similarity	NPD7411	Suspended
0.6632	Remote Similarity	NPD2186	Approved
0.6632	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6632	Remote Similarity	NPD5890	Approved
0.6632	Remote Similarity	NPD1512	Approved
0.6631	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6631	Remote Similarity	NPD4628	Phase 3
0.663	Remote Similarity	NPD1510	Phase 2
0.6622	Remote Similarity	NPD6997	Phase 2
0.6622	Remote Similarity	NPD8404	Phase 2
0.6621	Remote Similarity	NPD5676	Approved
0.6618	Remote Similarity	NPD7549	Discontinued
0.6616	Remote Similarity	NPD7199	Phase 2
0.6616	Remote Similarity	NPD6959	Discontinued
0.6615	Remote Similarity	NPD4005	Discontinued
0.6615	Remote Similarity	NPD824	Approved
0.6605	Remote Similarity	NPD7064	Clinical (unspecified phase)
0.6602	Remote Similarity	NPD3153	Approved
0.6602	Remote Similarity	NPD3154	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