NPASS Compound

Structure

NPC470898 OpenBabel07101719152D 46 50 0 0 1 0 0 0 0 0999 V2000 3.6272 -1.3458 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2805 -1.3458 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1344 -2.9708 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1797 -0.6946 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7584 -1.8951 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4539 -0.8685 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1785 -2.3824 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6481 -0.9506 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6272 -2.3003 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2805 -2.3003 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3972 -3.2268 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6673 -1.0270 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9739 -1.3458 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.3090 -2.0500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6040 -1.5390 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4539 -2.7776 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8847 -2.8944 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6232 -1.6154 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1473 -0.8685 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8406 -2.3060 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0915 -1.8714 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9739 0.5632 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.1473 0.0860 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.4539 0.0860 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7620 -2.4703 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4325 -0.4013 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8006 0.0860 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.8006 -2.7776 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.1072 -2.7776 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.4685 -4.1787 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5272 -0.6128 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.4539 -3.7321 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7447 -3.3086 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4118 -2.1531 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.3207 -1.3458 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4179 -1.2306 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9489 -3.7751 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.9739 1.5178 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.2805 0.5632 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8333 -3.4222 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2212 0.1364 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3258 -2.2964 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.8006 -0.8685 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.6272 0.5632 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.5638 0.1739 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 6 2 0 0 0 0 1 9 1 0 0 0 0 2 6 1 0 0 0 0 2 10 2 0 0 0 0 3 7 2 0 0 0 0 3 11 1 0 0 0 0 4 8 2 0 0 0 0 4 12 1 0 0 0 0 5 42 1 0 0 0 0 6 24 1 0 0 0 0 7 14 1 0 0 0 0 7 25 1 0 0 0 0 8 15 1 0 0 0 0 8 26 1 0 0 0 0 9 16 2 0 0 0 0 9 28 1 0 0 0 0 10 16 1 0 0 0 0 10 29 1 0 0 0 0 11 17 2 0 0 0 0 11 30 1 0 0 0 0 12 18 2 0 0 0 0 12 31 1 0 0 0 0 13 5 1 6 0 0 0 13 19 1 0 0 0 0 13 43 1 0 0 0 0 14 15 1 0 0 0 0 14 20 2 0 0 0 0 15 21 2 0 0 0 0 16 32 1 0 0 0 0 17 20 1 0 0 0 0 17 33 1 0 0 0 0 18 21 1 0 0 0 0 18 34 1 0 0 0 0 19 23 1 0 0 0 0 19 35 1 1 0 0 0 20 36 1 0 0 0 0 21 37 1 0 0 0 0 22 23 1 0 0 0 0 22 27 1 0 0 0 0 22 38 1 1 0 0 0 23 45 1 6 0 0 0 24 39 2 0 0 0 0 24 44 1 0 0 0 0 25 40 2 0 0 0 0 25 42 1 0 0 0 0 26 41 2 0 0 0 0 26 46 1 0 0 0 0 27 43 1 0 0 0 0 27 44 1 6 0 0 0 45 46 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	650.08
Volume:	568.143
LogP:	1.001
LogD:	0.553
LogS:	-2.522
# Rotatable Bonds:	3
TPSA:	319.89
# H-Bond Aceptor:	19
# H-Bond Donor:	11
# Rings:	5
# Heavy Atoms:	19

MedChem Properties

QED Drug-Likeness Score:	0.096
Synthetic Accessibility Score:	6.038
Fsp3:	0.222
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	2
Golden Triangle Rule:	Rejected
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.958
MDCK Permeability:	1.022691503749229e-05
Pgp-inhibitor:	0.16
Pgp-substrate:	0.02
Human Intestinal Absorption (HIA):	0.979
20% Bioavailability (F20%):	0.925
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.006
Plasma Protein Binding (PPB):	90.01110076904297%
Volume Distribution (VD):	0.567
Pgp-substrate:	23.94759750366211%

ADMET: Metabolism

CYP1A2-inhibitor:	0.102
CYP1A2-substrate:	0.009
CYP2C19-inhibitor:	0.013
CYP2C19-substrate:	0.027
CYP2C9-inhibitor:	0.417
CYP2C9-substrate:	0.036
CYP2D6-inhibitor:	0.002
CYP2D6-substrate:	0.094
CYP3A4-inhibitor:	0.02
CYP3A4-substrate:	0.002

ADMET: Excretion

Clearance (CL):	6.512
Half-life (T1/2):	0.957

ADMET: Toxicity

hERG Blockers:	0.204
Human Hepatotoxicity (H-HT):	0.157
Drug-inuced Liver Injury (DILI):	0.975
AMES Toxicity:	0.211
Rat Oral Acute Toxicity:	0.0
Maximum Recommended Daily Dose:	0.007
Skin Sensitization:	0.958
Carcinogencity:	0.013
Eye Corrosion:	0.003
Eye Irritation:	0.916
Respiratory Toxicity:	0.01

Download Data

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

Natural Product: NPC470898

Natural Product ID:	NPC470898
*Common Name:**	NXNXSPPXUHVUAL-XIGLUPEJSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	NXNXSPPXUHVUAL-XIGLUPEJSA-N
Standard InCHI:	InChI=1S/C27H22O19/c28-9-1-6(2-10(29)16(9)32)24(39)44-27-22(38)23-19(35)13(43-27)5-42-25(40)7-3-11(30)17(33)20(36)14(7)15-8(26(41)46-45-23)4-12(31)18(34)21(15)37/h1-4,13,19,22-23,27-38H,5H2/t13-,19-,22-,23+,27+/m1/s1
SMILES:	O[C@@H]1[C@H]2COC(=O)c3cc(O)c(c(c3c3c(C(=O)OO[C@@H]1[C@H]([C@@H](O2)OC(=O)c1cc(O)c(c(c1)O)O)O)cc(O)c(c3O)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2303749
PubChem CID:	71719654
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000238] Tannins [CHEMONTID:0001710] Hydrolyzable tannins

*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
NPO33256	green tea	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[14592472]

☑ 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
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT740	Individual Protein	Beta-secretase 1	Homo sapiens	IC50	>	160000.0	nM	PMID[514214]

☑ 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 NPC470898 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	390
0.1-0.2	1579
0.2-0.3	3429
0.3-0.4	7813
0.4-0.5	9707
0.5-0.6	5517
0.6-0.7	6309
0.7-0.8	6590
0.8-0.85	1078
0.85-0.9	226
0.9-0.95	44
0.95-1	15

Similarity Score	Similarity Level	Natural Product ID
0.9935	High Similarity	NPC291957
0.9935	High Similarity	NPC14030
0.9684	High Similarity	NPC311389
0.9684	High Similarity	NPC470271
0.962	High Similarity	NPC175793
0.9563	High Similarity	NPC470272
0.956	High Similarity	NPC190204
0.956	High Similarity	NPC43918
0.956	High Similarity	NPC261411
0.9441	High Similarity	NPC47521
0.9437	High Similarity	NPC31034
0.9423	High Similarity	NPC474010
0.9423	High Similarity	NPC135222
0.9416	High Similarity	NPC61152
0.9416	High Similarity	NPC205037
0.9416	High Similarity	NPC16024
0.9416	High Similarity	NPC44260
0.9416	High Similarity	NPC3746
0.9329	High Similarity	NPC297574
0.9329	High Similarity	NPC472723
0.9217	High Similarity	NPC80956
0.9177	High Similarity	NPC172419
0.9177	High Similarity	NPC238419
0.9161	High Similarity	NPC140151
0.9156	High Similarity	NPC92117
0.9114	High Similarity	NPC239019
0.9114	High Similarity	NPC247629
0.9102	High Similarity	NPC198902
0.9091	High Similarity	NPC142528
0.9091	High Similarity	NPC120621
0.9091	High Similarity	NPC248257
0.908	High Similarity	NPC217781
0.9074	High Similarity	NPC162169
0.9074	High Similarity	NPC166851
0.9053	High Similarity	NPC231254
0.9048	High Similarity	NPC8940
0.9048	High Similarity	NPC208797
0.9048	High Similarity	NPC53680
0.9036	High Similarity	NPC171706
0.9018	High Similarity	NPC317671
0.9018	High Similarity	NPC26536
0.9018	High Similarity	NPC49983
0.9018	High Similarity	NPC142707
0.9	High Similarity	NPC318826
0.9	High Similarity	NPC114791
0.9	High Similarity	NPC261623
0.9	High Similarity	NPC111490
0.9	High Similarity	NPC104222
0.9	High Similarity	NPC141331
0.9	High Similarity	NPC210501
0.8982	High Similarity	NPC79736
0.8982	High Similarity	NPC67629
0.8976	High Similarity	NPC166674
0.8976	High Similarity	NPC473550
0.8976	High Similarity	NPC219600
0.8976	High Similarity	NPC46640
0.8976	High Similarity	NPC263119
0.8976	High Similarity	NPC34436
0.897	High Similarity	NPC181778
0.8947	High Similarity	NPC65489
0.8944	High Similarity	NPC24627
0.8944	High Similarity	NPC289346
0.8938	High Similarity	NPC257309
0.8931	High Similarity	NPC203757
0.8929	High Similarity	NPC267549
0.8903	High Similarity	NPC268366
0.8896	High Similarity	NPC469651
0.8896	High Similarity	NPC121290
0.8896	High Similarity	NPC108455
0.8895	High Similarity	NPC119094
0.8895	High Similarity	NPC173872
0.8889	High Similarity	NPC469650
0.8882	High Similarity	NPC129533
0.8882	High Similarity	NPC123259
0.8875	High Similarity	NPC104983
0.8875	High Similarity	NPC291948
0.8875	High Similarity	NPC250436
0.8875	High Similarity	NPC88803
0.8875	High Similarity	NPC300845
0.8869	High Similarity	NPC473713
0.8855	High Similarity	NPC204937
0.8855	High Similarity	NPC149011
0.8844	High Similarity	NPC469652
0.8844	High Similarity	NPC472720
0.8844	High Similarity	NPC93065
0.8844	High Similarity	NPC472721
0.8844	High Similarity	NPC472724
0.8844	High Similarity	NPC31208
0.8844	High Similarity	NPC160543
0.8837	High Similarity	NPC260521
0.8837	High Similarity	NPC469649
0.8834	High Similarity	NPC90905
0.8834	High Similarity	NPC285108
0.8834	High Similarity	NPC4013
0.8834	High Similarity	NPC33298
0.8831	High Similarity	NPC22176
0.8831	High Similarity	NPC121573
0.8831	High Similarity	NPC226738
0.8831	High Similarity	NPC229036
0.8831	High Similarity	NPC190587
0.8827	High Similarity	NPC24164
0.8824	High Similarity	NPC170203
0.882	High Similarity	NPC156818
0.882	High Similarity	NPC68324
0.882	High Similarity	NPC160512
0.882	High Similarity	NPC472860
0.882	High Similarity	NPC38779
0.882	High Similarity	NPC289322
0.882	High Similarity	NPC114179
0.8812	High Similarity	NPC472835
0.8812	High Similarity	NPC156624
0.8812	High Similarity	NPC172920
0.8802	High Similarity	NPC67134
0.8802	High Similarity	NPC47140
0.8793	High Similarity	NPC264302
0.879	High Similarity	NPC75945
0.8786	High Similarity	NPC7839
0.8786	High Similarity	NPC290289
0.8786	High Similarity	NPC477081
0.8786	High Similarity	NPC269046
0.8786	High Similarity	NPC223534
0.8786	High Similarity	NPC142291
0.8786	High Similarity	NPC240200
0.8786	High Similarity	NPC158214
0.8786	High Similarity	NPC477083
0.8765	High Similarity	NPC87317
0.8758	High Similarity	NPC318432
0.875	High Similarity	NPC172033
0.875	High Similarity	NPC88560
0.875	High Similarity	NPC175230
0.8736	High Similarity	NPC187632
0.8736	High Similarity	NPC201814
0.8735	High Similarity	NPC473818
0.8735	High Similarity	NPC311912
0.8728	High Similarity	NPC105591
0.8728	High Similarity	NPC237202
0.8726	High Similarity	NPC81835
0.8718	High Similarity	NPC474465
0.8712	High Similarity	NPC239966
0.8712	High Similarity	NPC203020
0.8712	High Similarity	NPC53889
0.8706	High Similarity	NPC258044
0.8706	High Similarity	NPC476619
0.8706	High Similarity	NPC469418
0.8706	High Similarity	NPC260300
0.8706	High Similarity	NPC476621
0.8706	High Similarity	NPC267680
0.8706	High Similarity	NPC217387
0.8706	High Similarity	NPC476623
0.8706	High Similarity	NPC476620
0.8706	High Similarity	NPC253521
0.8706	High Similarity	NPC293626
0.8706	High Similarity	NPC476622
0.8706	High Similarity	NPC196127
0.8706	High Similarity	NPC113836
0.8706	High Similarity	NPC37668
0.8706	High Similarity	NPC476618
0.8704	High Similarity	NPC4747
0.8704	High Similarity	NPC1913
0.8704	High Similarity	NPC104275
0.8693	High Similarity	NPC476358
0.869	High Similarity	NPC38438
0.8686	High Similarity	NPC97924
0.8686	High Similarity	NPC471091
0.8686	High Similarity	NPC40078
0.8683	High Similarity	NPC658
0.8683	High Similarity	NPC95421
0.8683	High Similarity	NPC198125
0.8683	High Similarity	NPC88557
0.8683	High Similarity	NPC197708
0.8679	High Similarity	NPC252979
0.8655	High Similarity	NPC195114
0.8655	High Similarity	NPC212290
0.865	High Similarity	NPC289811
0.865	High Similarity	NPC287872
0.865	High Similarity	NPC74319
0.865	High Similarity	NPC160780
0.8647	High Similarity	NPC472992
0.8647	High Similarity	NPC61904
0.8647	High Similarity	NPC472991
0.8647	High Similarity	NPC144097
0.8639	High Similarity	NPC472993
0.8634	High Similarity	NPC291510
0.8634	High Similarity	NPC281703
0.8634	High Similarity	NPC125487
0.8634	High Similarity	NPC144801
0.8634	High Similarity	NPC116850
0.8634	High Similarity	NPC197188
0.8634	High Similarity	NPC43872
0.8634	High Similarity	NPC238672
0.8623	High Similarity	NPC298847
0.8623	High Similarity	NPC45400
0.8623	High Similarity	NPC116745
0.8614	High Similarity	NPC165720
0.8614	High Similarity	NPC471788
0.8608	High Similarity	NPC476463
0.8608	High Similarity	NPC43123
0.8605	High Similarity	NPC469371
0.8598	High Similarity	NPC474770
0.8598	High Similarity	NPC166277

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 NPC470898 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	346
0.1-0.2	904
0.2-0.3	1826
0.3-0.4	2762
0.4-0.5	1894
0.5-0.6	1009
0.6-0.7	270
0.7-0.8	122
0.8-0.85	16
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8875	High Similarity	NPD4868	Clinical (unspecified phase)
0.8471	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8405	Intermediate Similarity	NPD1465	Phase 2
0.8402	Intermediate Similarity	NPD3818	Discontinued
0.8372	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8353	Intermediate Similarity	NPD5844	Phase 1
0.8304	Intermediate Similarity	NPD7472	Approved
0.8304	Intermediate Similarity	NPD7074	Phase 3
0.8294	Intermediate Similarity	NPD7228	Approved
0.8256	Intermediate Similarity	NPD6797	Phase 2
0.8253	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8246	Intermediate Similarity	NPD7054	Approved
0.8208	Intermediate Similarity	NPD7251	Discontinued
0.8204	Intermediate Similarity	NPD6234	Discontinued
0.8166	Intermediate Similarity	NPD6232	Discontinued
0.8121	Intermediate Similarity	NPD37	Approved
0.8084	Intermediate Similarity	NPD4966	Approved
0.8084	Intermediate Similarity	NPD4967	Phase 2
0.8084	Intermediate Similarity	NPD4965	Approved
0.807	Intermediate Similarity	NPD6166	Phase 2
0.807	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.807	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8065	Intermediate Similarity	NPD230	Phase 1
0.8063	Intermediate Similarity	NPD6190	Approved
0.8057	Intermediate Similarity	NPD7808	Phase 3
0.8038	Intermediate Similarity	NPD7266	Discontinued
0.8023	Intermediate Similarity	NPD7473	Discontinued
0.8	Intermediate Similarity	NPD7199	Phase 2
0.7937	Intermediate Similarity	NPD8151	Discontinued
0.7927	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.791	Intermediate Similarity	NPD8312	Approved
0.791	Intermediate Similarity	NPD8313	Approved
0.7904	Intermediate Similarity	NPD1934	Approved
0.7901	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7898	Intermediate Similarity	NPD7240	Approved
0.7898	Intermediate Similarity	NPD7685	Pre-registration
0.7898	Intermediate Similarity	NPD6559	Discontinued
0.7892	Intermediate Similarity	NPD4380	Phase 2
0.7889	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7857	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7821	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7803	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7771	Intermediate Similarity	NPD1653	Approved
0.7751	Intermediate Similarity	NPD8455	Phase 2
0.7727	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7688	Intermediate Similarity	NPD6959	Discontinued
0.767	Intermediate Similarity	NPD3751	Discontinued
0.7647	Intermediate Similarity	NPD2801	Approved
0.7647	Intermediate Similarity	NPD7819	Suspended
0.7636	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7616	Intermediate Similarity	NPD3749	Approved
0.7616	Intermediate Similarity	NPD7075	Discontinued
0.7602	Intermediate Similarity	NPD3817	Phase 2
0.7561	Intermediate Similarity	NPD3750	Approved
0.7558	Intermediate Similarity	NPD3882	Suspended
0.7547	Intermediate Similarity	NPD943	Approved
0.7543	Intermediate Similarity	NPD3787	Discontinued
0.7532	Intermediate Similarity	NPD3764	Approved
0.753	Intermediate Similarity	NPD1511	Approved
0.7529	Intermediate Similarity	NPD7411	Suspended
0.7527	Intermediate Similarity	NPD6534	Approved
0.7527	Intermediate Similarity	NPD6535	Approved
0.75	Intermediate Similarity	NPD5402	Approved
0.7487	Intermediate Similarity	NPD7435	Discontinued
0.7486	Intermediate Similarity	NPD8150	Discontinued
0.7485	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD9269	Phase 2
0.746	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7458	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7448	Intermediate Similarity	NPD8320	Phase 1
0.7448	Intermediate Similarity	NPD8319	Approved
0.7442	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.744	Intermediate Similarity	NPD1512	Approved
0.7439	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7429	Intermediate Similarity	NPD5494	Approved
0.7425	Intermediate Similarity	NPD7390	Discontinued
0.7421	Intermediate Similarity	NPD6781	Approved
0.7421	Intermediate Similarity	NPD6777	Approved
0.7421	Intermediate Similarity	NPD6776	Approved
0.7421	Intermediate Similarity	NPD6780	Approved
0.7421	Intermediate Similarity	NPD6778	Approved
0.7421	Intermediate Similarity	NPD6782	Approved
0.7421	Intermediate Similarity	NPD6779	Approved
0.7412	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD7699	Phase 2
0.7407	Intermediate Similarity	NPD7700	Phase 2
0.7399	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7398	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7398	Intermediate Similarity	NPD7783	Phase 2
0.7396	Intermediate Similarity	NPD7680	Approved
0.7384	Intermediate Similarity	NPD6801	Discontinued
0.7381	Intermediate Similarity	NPD2534	Approved
0.7381	Intermediate Similarity	NPD2533	Approved
0.7381	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7381	Intermediate Similarity	NPD2532	Approved
0.7362	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7356	Intermediate Similarity	NPD7768	Phase 2
0.7349	Intermediate Similarity	NPD4628	Phase 3
0.7333	Intermediate Similarity	NPD1549	Phase 2
0.7329	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD1613	Approved
0.7317	Intermediate Similarity	NPD5404	Approved
0.7317	Intermediate Similarity	NPD5406	Approved
0.7317	Intermediate Similarity	NPD5405	Approved
0.7317	Intermediate Similarity	NPD5408	Approved
0.7294	Intermediate Similarity	NPD5403	Approved
0.7287	Intermediate Similarity	NPD6212	Phase 3
0.7287	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.7287	Intermediate Similarity	NPD6213	Phase 3
0.7273	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7268	Intermediate Similarity	NPD7870	Phase 2
0.7268	Intermediate Similarity	NPD7871	Phase 2
0.7259	Intermediate Similarity	NPD7874	Approved
0.7259	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7256	Intermediate Similarity	NPD1510	Phase 2
0.7256	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7256	Intermediate Similarity	NPD3748	Approved
0.7219	Intermediate Similarity	NPD6799	Approved
0.7216	Intermediate Similarity	NPD7698	Approved
0.7216	Intermediate Similarity	NPD7696	Phase 3
0.7216	Intermediate Similarity	NPD7697	Approved
0.7209	Intermediate Similarity	NPD7458	Discontinued
0.7208	Intermediate Similarity	NPD9268	Approved
0.7189	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7186	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD5401	Approved
0.7168	Intermediate Similarity	NPD6599	Discontinued
0.7165	Intermediate Similarity	NPD6823	Phase 2
0.7157	Intermediate Similarity	NPD7701	Phase 2
0.7143	Intermediate Similarity	NPD3027	Phase 3
0.7143	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD8166	Discontinued
0.7125	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD6674	Discontinued
0.7081	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7076	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7056	Intermediate Similarity	NPD7229	Phase 3
0.705	Intermediate Similarity	NPD7801	Approved
0.7017	Intermediate Similarity	NPD3926	Phase 2
0.7017	Intermediate Similarity	NPD5242	Approved
0.7012	Intermediate Similarity	NPD1240	Approved
0.7011	Intermediate Similarity	NPD3226	Approved
0.7006	Intermediate Similarity	NPD2796	Approved
0.7006	Intermediate Similarity	NPD5353	Approved
0.7006	Intermediate Similarity	NPD2935	Discontinued
0.6994	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.699	Remote Similarity	NPD8155	Clinical (unspecified phase)
0.6985	Remote Similarity	NPD7585	Approved
0.697	Remote Similarity	NPD7211	Clinical (unspecified phase)
0.6961	Remote Similarity	NPD5710	Approved
0.6961	Remote Similarity	NPD5711	Approved
0.6941	Remote Similarity	NPD7003	Approved
0.6941	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6935	Remote Similarity	NPD7583	Approved
0.6931	Remote Similarity	NPD8434	Phase 2
0.6928	Remote Similarity	NPD1607	Approved
0.6923	Remote Similarity	NPD9545	Approved
0.6914	Remote Similarity	NPD3455	Phase 2
0.6906	Remote Similarity	NPD8127	Discontinued
0.6905	Remote Similarity	NPD1551	Phase 2
0.6889	Remote Similarity	NPD919	Approved
0.6886	Remote Similarity	NPD4978	Clinical (unspecified phase)
0.6871	Remote Similarity	NPD4908	Phase 1
0.6867	Remote Similarity	NPD1933	Approved
0.6863	Remote Similarity	NPD7930	Approved
0.685	Remote Similarity	NPD7584	Approved
0.6839	Remote Similarity	NPD6273	Approved
0.6829	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6821	Remote Similarity	NPD8090	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD5006	Approved
0.6818	Remote Similarity	NPD5005	Approved
0.6816	Remote Similarity	NPD4288	Approved
0.6811	Remote Similarity	NPD7177	Discontinued
0.681	Remote Similarity	NPD9494	Approved
0.6805	Remote Similarity	NPD6099	Approved
0.6805	Remote Similarity	NPD6100	Approved
0.6802	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.679	Remote Similarity	NPD1470	Approved
0.6788	Remote Similarity	NPD6798	Discontinued
0.6788	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD8470	Clinical (unspecified phase)
0.6771	Remote Similarity	NPD4287	Approved
0.6766	Remote Similarity	NPD447	Suspended
0.6765	Remote Similarity	NPD2029	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD2346	Discontinued
0.6762	Remote Similarity	NPD5619	Clinical (unspecified phase)
0.6742	Remote Similarity	NPD6386	Approved
0.6742	Remote Similarity	NPD6385	Approved
0.6721	Remote Similarity	NPD1247	Approved
0.672	Remote Similarity	NPD7549	Discontinued
0.672	Remote Similarity	NPD7799	Discontinued
0.6719	Remote Similarity	NPD6842	Approved
0.6719	Remote Similarity	NPD6843	Phase 3
0.6719	Remote Similarity	NPD6841	Approved
0.6716	Remote Similarity	NPD7999	Approved
0.6705	Remote Similarity	NPD920	Approved
0.6702	Remote Similarity	NPD5953	Discontinued
0.6701	Remote Similarity	NPD4420	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