NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	492.09
Volume:	445.387
LogP:	0.775
LogD:	-0.05
LogS:	-4.124
# Rotatable Bonds:	5
TPSA:	227.58
# H-Bond Aceptor:	13
# H-Bond Donor:	8
# Rings:	4
# Heavy Atoms:	13

MedChem Properties

QED Drug-Likeness Score:	0.215
Synthetic Accessibility Score:	4.436
Fsp3:	0.273
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.082
MDCK Permeability:	8.403928404732142e-06
Pgp-inhibitor:	0.289
Pgp-substrate:	0.987
Human Intestinal Absorption (HIA):	0.751
20% Bioavailability (F20%):	0.228
30% Bioavailability (F30%):	0.99

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.006
Plasma Protein Binding (PPB):	87.4981460571289%
Volume Distribution (VD):	0.842
Pgp-substrate:	15.253228187561035%

ADMET: Metabolism

CYP1A2-inhibitor:	0.108
CYP1A2-substrate:	0.137
CYP2C19-inhibitor:	0.013
CYP2C19-substrate:	0.043
CYP2C9-inhibitor:	0.097
CYP2C9-substrate:	0.193
CYP2D6-inhibitor:	0.021
CYP2D6-substrate:	0.157
CYP3A4-inhibitor:	0.086
CYP3A4-substrate:	0.019

ADMET: Excretion

Clearance (CL):	4.287
Half-life (T1/2):	0.916

ADMET: Toxicity

hERG Blockers:	0.168
Human Hepatotoxicity (H-HT):	0.167
Drug-inuced Liver Injury (DILI):	0.979
AMES Toxicity:	0.744
Rat Oral Acute Toxicity:	0.023
Maximum Recommended Daily Dose:	0.025
Skin Sensitization:	0.94
Carcinogencity:	0.019
Eye Corrosion:	0.003
Eye Irritation:	0.802
Respiratory Toxicity:	0.031

Download Data

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

Natural Product: NPC476771

Natural Product ID:	NPC476771
*Common Name:**	3-[(2S,3R,4R,5S)-4-acetyl-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy-5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)chromen-4-one
IUPAC Name:	3-[(2S,3R,4R,5S)-4-acetyl-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy-5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)chromen-4-one
Synonyms:
Standard InCHIKey:	LDGQEEQKCJWNHB-SVWBVHECSA-N
Standard InCHI:	InChI=1S/C22H20O13/c1-7(24)22(32)14(6-23)34-21(20(22)31)35-19-17(30)15-10(26)4-9(25)5-13(15)33-18(19)8-2-11(27)16(29)12(28)3-8/h2-5,14,20-21,23,25-29,31-32H,6H2,1H3/t14-,20-,21-,22-/m0/s1
SMILES:	CC(=O)[C@@]1([C@@H](O[C@H]([C@@H]1O)OC2=C(OC3=CC(=CC(=C3C2=O)O)O)C4=CC(=C(C(=C4)O)O)O)CO)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	44583836
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001111] Flavonoid glycosides [CHEMONTID:0001583] Flavonoid O-glycosides [CHEMONTID:0003531] Flavonoid-3-O-glycosides

*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
NPO33517	Calycolpus warszewiczianus	Species	Myrtaceae	Eukaryota	young leaves	Barro Colorado Nature Monument in Gatn Lake, Republic of Panama	2004-FEB	PMID[16724851]

☑ 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
IC50	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	>	50000	nM	PMID[16724851]

☑ 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 NPC476771 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	424
0.1-0.2	1795
0.2-0.3	3990
0.3-0.4	9257
0.4-0.5	9227
0.5-0.6	4254
0.6-0.7	5261
0.7-0.8	5362
0.8-0.85	1744
0.85-0.9	1152
0.9-0.95	223
0.95-1	8

Similarity Score	Similarity Level	Natural Product ID
0.9875	High Similarity	NPC476772
0.981	High Similarity	NPC34531
0.9752	High Similarity	NPC245452
0.9748	High Similarity	NPC67037
0.9748	High Similarity	NPC255615
0.9625	High Similarity	NPC135599
0.9625	High Similarity	NPC254306
0.9625	High Similarity	NPC113968
0.9625	High Similarity	NPC277174
0.9625	High Similarity	NPC328940
0.9625	High Similarity	NPC73855
0.9568	High Similarity	NPC72249
0.9565	High Similarity	NPC84362
0.9565	High Similarity	NPC226304
0.9565	High Similarity	NPC149244
0.9565	High Similarity	NPC48640
0.9565	High Similarity	NPC127546
0.9565	High Similarity	NPC265530
0.9565	High Similarity	NPC317489
0.9565	High Similarity	NPC52550
0.9565	High Similarity	NPC173637
0.9565	High Similarity	NPC325555
0.9565	High Similarity	NPC223424
0.9563	High Similarity	NPC240431
0.9563	High Similarity	NPC55786
0.9563	High Similarity	NPC19388
0.9509	High Similarity	NPC175107
0.9509	High Similarity	NPC190003
0.9506	High Similarity	NPC120099
0.9506	High Similarity	NPC225434
0.9506	High Similarity	NPC203050
0.9506	High Similarity	NPC223747
0.9506	High Similarity	NPC219904
0.9506	High Similarity	NPC138927
0.9503	High Similarity	NPC179950
0.9503	High Similarity	NPC118284
0.9503	High Similarity	NPC253662
0.9503	High Similarity	NPC88789
0.9503	High Similarity	NPC56077
0.9503	High Similarity	NPC308404
0.9503	High Similarity	NPC276222
0.9503	High Similarity	NPC274618
0.9503	High Similarity	NPC145038
0.9503	High Similarity	NPC281131
0.9455	High Similarity	NPC154741
0.9455	High Similarity	NPC296018
0.9451	High Similarity	NPC101026
0.9451	High Similarity	NPC42773
0.9451	High Similarity	NPC4390
0.9451	High Similarity	NPC45522
0.9451	High Similarity	NPC21666
0.9451	High Similarity	NPC24043
0.9451	High Similarity	NPC169977
0.9448	High Similarity	NPC20505
0.9448	High Similarity	NPC206123
0.9448	High Similarity	NPC155763
0.9448	High Similarity	NPC212748
0.9448	High Similarity	NPC244776
0.9448	High Similarity	NPC116864
0.9448	High Similarity	NPC95866
0.9448	High Similarity	NPC235260
0.9444	High Similarity	NPC76482
0.9441	High Similarity	NPC277205
0.9437	High Similarity	NPC473043
0.9401	High Similarity	NPC473071
0.9401	High Similarity	NPC473073
0.9398	High Similarity	NPC476773
0.939	High Similarity	NPC155877
0.939	High Similarity	NPC134532
0.939	High Similarity	NPC471748
0.939	High Similarity	NPC203259
0.939	High Similarity	NPC176740
0.939	High Similarity	NPC153755
0.939	High Similarity	NPC33054
0.939	High Similarity	NPC476405
0.939	High Similarity	NPC235575
0.939	High Similarity	NPC117260
0.939	High Similarity	NPC471725
0.9387	High Similarity	NPC270578
0.9387	High Similarity	NPC227508
0.9387	High Similarity	NPC52382
0.9383	High Similarity	NPC21100
0.9383	High Similarity	NPC197285
0.9379	High Similarity	NPC284960
0.9379	High Similarity	NPC19709
0.9379	High Similarity	NPC222936
0.9345	High Similarity	NPC473072
0.9337	High Similarity	NPC65563
0.9337	High Similarity	NPC472385
0.9337	High Similarity	NPC198324
0.9337	High Similarity	NPC470949
0.9329	High Similarity	NPC136042
0.9329	High Similarity	NPC84265
0.9329	High Similarity	NPC245014
0.9329	High Similarity	NPC282987
0.9329	High Similarity	NPC67326
0.9329	High Similarity	NPC67105
0.9329	High Similarity	NPC156869
0.9329	High Similarity	NPC29958
0.9329	High Similarity	NPC259896
0.9329	High Similarity	NPC255157
0.9329	High Similarity	NPC254855
0.9325	High Similarity	NPC92565
0.9325	High Similarity	NPC275454
0.9325	High Similarity	NPC160156
0.9321	High Similarity	NPC311830
0.9321	High Similarity	NPC22832
0.9317	High Similarity	NPC300537
0.9317	High Similarity	NPC77660
0.9317	High Similarity	NPC127782
0.9317	High Similarity	NPC150164
0.9317	High Similarity	NPC189142
0.9308	High Similarity	NPC288084
0.9281	High Similarity	NPC258044
0.9281	High Similarity	NPC293626
0.9281	High Similarity	NPC196127
0.9281	High Similarity	NPC168584
0.9281	High Similarity	NPC267680
0.9281	High Similarity	NPC35167
0.9281	High Similarity	NPC217387
0.9277	High Similarity	NPC294629
0.9277	High Similarity	NPC476472
0.9277	High Similarity	NPC115760
0.9277	High Similarity	NPC43211
0.9277	High Similarity	NPC16194
0.9277	High Similarity	NPC264735
0.9277	High Similarity	NPC220173
0.9277	High Similarity	NPC19108
0.9277	High Similarity	NPC49344
0.9277	High Similarity	NPC135277
0.9277	High Similarity	NPC473327
0.9277	High Similarity	NPC294815
0.9277	High Similarity	NPC210094
0.9277	High Similarity	NPC101191
0.9277	High Similarity	NPC477848
0.9277	High Similarity	NPC253685
0.9277	High Similarity	NPC237435
0.9273	High Similarity	NPC60735
0.9273	High Similarity	NPC26230
0.9273	High Similarity	NPC261254
0.9268	High Similarity	NPC469931
0.9268	High Similarity	NPC45638
0.9268	High Similarity	NPC58053
0.9268	High Similarity	NPC226294
0.9268	High Similarity	NPC186807
0.9268	High Similarity	NPC93337
0.9268	High Similarity	NPC201292
0.9268	High Similarity	NPC475942
0.9268	High Similarity	NPC105025
0.9264	High Similarity	NPC210073
0.9264	High Similarity	NPC115674
0.9259	High Similarity	NPC309025
0.9259	High Similarity	NPC88043
0.9259	High Similarity	NPC88023
0.9259	High Similarity	NPC191306
0.9259	High Similarity	NPC243930
0.9259	High Similarity	NPC94777
0.9259	High Similarity	NPC168822
0.9259	High Similarity	NPC270335
0.9226	High Similarity	NPC110941
0.9226	High Similarity	NPC470443
0.9226	High Similarity	NPC241423
0.9226	High Similarity	NPC126784
0.9226	High Similarity	NPC473682
0.9226	High Similarity	NPC473571
0.9226	High Similarity	NPC470444
0.9222	High Similarity	NPC122467
0.9222	High Similarity	NPC144097
0.9222	High Similarity	NPC61904
0.9222	High Similarity	NPC471669
0.9222	High Similarity	NPC233994
0.9222	High Similarity	NPC8573
0.9222	High Similarity	NPC14187
0.9222	High Similarity	NPC202908
0.9222	High Similarity	NPC211532
0.9222	High Similarity	NPC169733
0.9222	High Similarity	NPC89127
0.9222	High Similarity	NPC257714
0.9222	High Similarity	NPC292019
0.9212	High Similarity	NPC285197
0.9212	High Similarity	NPC224462
0.9207	High Similarity	NPC45618
0.9207	High Similarity	NPC116745
0.9207	High Similarity	NPC58716
0.9207	High Similarity	NPC146792
0.9207	High Similarity	NPC229729
0.9207	High Similarity	NPC42892
0.9202	High Similarity	NPC165720
0.9202	High Similarity	NPC72016
0.9193	High Similarity	NPC269906
0.9193	High Similarity	NPC110349
0.9167	High Similarity	NPC253521
0.9167	High Similarity	NPC89052
0.9167	High Similarity	NPC139571
0.9167	High Similarity	NPC251417
0.9167	High Similarity	NPC113836
0.9167	High Similarity	NPC37668
0.9167	High Similarity	NPC217520
0.9167	High Similarity	NPC173837
0.9162	High Similarity	NPC223426

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 NPC476771 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	375
0.1-0.2	914
0.2-0.3	2053
0.3-0.4	2695
0.4-0.5	1799
0.5-0.6	887
0.6-0.7	283
0.7-0.8	108
0.8-0.85	14
0.85-0.9	20
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9444	High Similarity	NPD3818	Discontinued
0.939	High Similarity	NPD6797	Phase 2
0.9333	High Similarity	NPD7251	Discontinued
0.9277	High Similarity	NPD4338	Clinical (unspecified phase)
0.9162	High Similarity	NPD7808	Phase 3
0.9152	High Similarity	NPD7054	Approved
0.9096	High Similarity	NPD7472	Approved
0.9006	High Similarity	NPD3882	Suspended
0.8982	High Similarity	NPD7074	Phase 3
0.8834	High Similarity	NPD4381	Clinical (unspecified phase)
0.8827	High Similarity	NPD3817	Phase 2
0.881	High Similarity	NPD7804	Clinical (unspecified phase)
0.8765	High Similarity	NPD2801	Approved
0.8743	High Similarity	NPD6167	Clinical (unspecified phase)
0.8743	High Similarity	NPD6166	Phase 2
0.8743	High Similarity	NPD6168	Clinical (unspecified phase)
0.8704	High Similarity	NPD1934	Approved
0.8679	High Similarity	NPD1512	Approved
0.865	High Similarity	NPD2393	Clinical (unspecified phase)
0.8553	High Similarity	NPD1511	Approved
0.8439	Intermediate Similarity	NPD6559	Discontinued
0.8434	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8383	Intermediate Similarity	NPD7075	Discontinued
0.8373	Intermediate Similarity	NPD5402	Approved
0.8364	Intermediate Similarity	NPD6801	Discontinued
0.8276	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8272	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8242	Intermediate Similarity	NPD4380	Phase 2
0.821	Intermediate Similarity	NPD6799	Approved
0.8204	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8171	Intermediate Similarity	NPD5403	Approved
0.807	Intermediate Similarity	NPD5494	Approved
0.8049	Intermediate Similarity	NPD5401	Approved
0.8035	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.8022	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.8012	Intermediate Similarity	NPD6234	Discontinued
0.8	Intermediate Similarity	NPD3751	Discontinued
0.7977	Intermediate Similarity	NPD3787	Discontinued
0.7952	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.795	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.795	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7929	Intermediate Similarity	NPD37	Approved
0.7921	Intermediate Similarity	NPD7685	Pre-registration
0.7919	Intermediate Similarity	NPD7199	Phase 2
0.7919	Intermediate Similarity	NPD1247	Approved
0.7917	Intermediate Similarity	NPD6599	Discontinued
0.7907	Intermediate Similarity	NPD919	Approved
0.7904	Intermediate Similarity	NPD1653	Approved
0.7901	Intermediate Similarity	NPD1549	Phase 2
0.7898	Intermediate Similarity	NPD7228	Approved
0.7895	Intermediate Similarity	NPD4967	Phase 2
0.7895	Intermediate Similarity	NPD4966	Approved
0.7895	Intermediate Similarity	NPD4965	Approved
0.7888	Intermediate Similarity	NPD2796	Approved
0.7874	Intermediate Similarity	NPD6232	Discontinued
0.7866	Intermediate Similarity	NPD6190	Approved
0.7845	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7841	Intermediate Similarity	NPD7473	Discontinued
0.7831	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7829	Intermediate Similarity	NPD3926	Phase 2
0.7826	Intermediate Similarity	NPD1510	Phase 2
0.7778	Intermediate Similarity	NPD7819	Suspended
0.7778	Intermediate Similarity	NPD1465	Phase 2
0.7733	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7714	Intermediate Similarity	NPD6959	Discontinued
0.7697	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7683	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7665	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7661	Intermediate Similarity	NPD7411	Suspended
0.7654	Intermediate Similarity	NPD5844	Phase 1
0.764	Intermediate Similarity	NPD230	Phase 1
0.7632	Intermediate Similarity	NPD6782	Approved
0.7632	Intermediate Similarity	NPD6779	Approved
0.7632	Intermediate Similarity	NPD6778	Approved
0.7632	Intermediate Similarity	NPD6777	Approved
0.7632	Intermediate Similarity	NPD6776	Approved
0.7632	Intermediate Similarity	NPD6780	Approved
0.7632	Intermediate Similarity	NPD6781	Approved
0.7619	Intermediate Similarity	NPD2534	Approved
0.7619	Intermediate Similarity	NPD2532	Approved
0.7619	Intermediate Similarity	NPD2533	Approved
0.7604	Intermediate Similarity	NPD7435	Discontinued
0.7578	Intermediate Similarity	NPD1240	Approved
0.7578	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7578	Intermediate Similarity	NPD943	Approved
0.7578	Intermediate Similarity	NPD1613	Approved
0.7543	Intermediate Similarity	NPD3749	Approved
0.7541	Intermediate Similarity	NPD8313	Approved
0.7541	Intermediate Similarity	NPD8312	Approved
0.753	Intermediate Similarity	NPD2800	Approved
0.7527	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7514	Intermediate Similarity	NPD8434	Phase 2
0.7487	Intermediate Similarity	NPD7584	Approved
0.7485	Intermediate Similarity	NPD1607	Approved
0.7432	Intermediate Similarity	NPD7240	Approved
0.7427	Intermediate Similarity	NPD920	Approved
0.7423	Intermediate Similarity	NPD7698	Approved
0.7423	Intermediate Similarity	NPD7696	Phase 3
0.7423	Intermediate Similarity	NPD7697	Approved
0.7411	Intermediate Similarity	NPD8151	Discontinued
0.741	Intermediate Similarity	NPD7266	Discontinued
0.7394	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD3027	Phase 3
0.7389	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7385	Intermediate Similarity	NPD7870	Phase 2
0.7385	Intermediate Similarity	NPD7871	Phase 2
0.7382	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7381	Intermediate Similarity	NPD3750	Approved
0.7381	Intermediate Similarity	NPD4628	Phase 3
0.7375	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7374	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7374	Intermediate Similarity	NPD7874	Approved
0.7368	Intermediate Similarity	NPD6535	Approved
0.7368	Intermediate Similarity	NPD6534	Approved
0.736	Intermediate Similarity	NPD7701	Phase 2
0.7349	Intermediate Similarity	NPD1551	Phase 2
0.7346	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7321	Intermediate Similarity	NPD1243	Approved
0.7317	Intermediate Similarity	NPD447	Suspended
0.7317	Intermediate Similarity	NPD1933	Approved
0.731	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7293	Intermediate Similarity	NPD2403	Approved
0.7289	Intermediate Similarity	NPD7033	Discontinued
0.7288	Intermediate Similarity	NPD7768	Phase 2
0.7254	Intermediate Similarity	NPD7699	Phase 2
0.7254	Intermediate Similarity	NPD7700	Phase 2
0.725	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD7783	Phase 2
0.725	Intermediate Similarity	NPD7801	Approved
0.7246	Intermediate Similarity	NPD2935	Discontinued
0.7219	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7208	Intermediate Similarity	NPD8320	Phase 1
0.7208	Intermediate Similarity	NPD8319	Approved
0.7202	Intermediate Similarity	NPD2344	Approved
0.7194	Intermediate Similarity	NPD6823	Phase 2
0.7193	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7189	Intermediate Similarity	NPD5953	Discontinued
0.7175	Intermediate Similarity	NPD8455	Phase 2
0.7143	Intermediate Similarity	NPD6099	Approved
0.7143	Intermediate Similarity	NPD3226	Approved
0.7143	Intermediate Similarity	NPD6100	Approved
0.7143	Intermediate Similarity	NPD8150	Discontinued
0.7134	Intermediate Similarity	NPD6798	Discontinued
0.7128	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7108	Intermediate Similarity	NPD6355	Discontinued
0.7104	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.71	Intermediate Similarity	NPD7585	Approved
0.7092	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD6233	Phase 2
0.7088	Intermediate Similarity	NPD5710	Approved
0.7088	Intermediate Similarity	NPD5711	Approved
0.7083	Intermediate Similarity	NPD3748	Approved
0.7081	Intermediate Similarity	NPD7286	Phase 2
0.7066	Intermediate Similarity	NPD6651	Approved
0.7055	Intermediate Similarity	NPD9494	Approved
0.705	Intermediate Similarity	NPD7583	Approved
0.7037	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7035	Intermediate Similarity	NPD2309	Approved
0.7033	Intermediate Similarity	NPD5619	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD2313	Discontinued
0.7027	Intermediate Similarity	NPD2163	Approved
0.7019	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.7012	Intermediate Similarity	NPD6832	Phase 2
0.7011	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD1091	Approved
0.6994	Remote Similarity	NPD2798	Approved
0.6985	Remote Similarity	NPD7680	Approved
0.6982	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.6982	Remote Similarity	NPD2799	Discontinued
0.6977	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6976	Remote Similarity	NPD7930	Approved
0.6957	Remote Similarity	NPD9269	Phase 2
0.6954	Remote Similarity	NPD7390	Discontinued
0.6949	Remote Similarity	NPD7458	Discontinued
0.6944	Remote Similarity	NPD5353	Approved
0.6935	Remote Similarity	NPD5005	Approved
0.6935	Remote Similarity	NPD5006	Approved
0.6933	Remote Similarity	NPD1203	Approved
0.6927	Remote Similarity	NPD6844	Discontinued
0.6923	Remote Similarity	NPD4363	Phase 3
0.6923	Remote Similarity	NPD4360	Phase 2
0.6919	Remote Similarity	NPD6674	Discontinued
0.6919	Remote Similarity	NPD2654	Approved
0.6919	Remote Similarity	NPD1652	Phase 2
0.6914	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6902	Remote Similarity	NPD7229	Phase 3
0.6901	Remote Similarity	NPD2346	Discontinued
0.6888	Remote Similarity	NPD4362	Clinical (unspecified phase)
0.6888	Remote Similarity	NPD4361	Phase 2
0.6884	Remote Similarity	NPD2493	Approved
0.6884	Remote Similarity	NPD2494	Approved
0.6872	Remote Similarity	NPD6214	Clinical (unspecified phase)
0.6872	Remote Similarity	NPD6213	Phase 3
0.6872	Remote Similarity	NPD6212	Phase 3
0.6865	Remote Similarity	NPD5242	Approved
0.686	Remote Similarity	NPD2424	Discontinued

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