NPASS Compound

Structure

NPC475360 OpenBabel07101719252D 48 52 0 0 1 0 0 0 0 0999 V2000 11.8551 -5.8962 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.1558 -5.8962 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 12.7048 -6.3868 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.1558 -4.9151 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 11.0054 -7.3679 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0576 -2.9528 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0525 -5.5893 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.6067 -3.4434 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 11.0054 -6.3868 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0576 -3.9340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 12.7048 -7.3679 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 11.8551 -7.8585 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2080 -2.4623 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.4564 -2.9528 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 1.4758 -4.7956 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 11.0054 -4.4245 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2080 -4.4245 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0040 -5.3842 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 3.3583 -2.9528 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.4564 -1.9717 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 9.3061 -1.4811 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 10.1558 -1.9717 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 3.3583 -3.9340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4030 -6.2805 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 5.3627 -6.4845 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7570 -4.9151 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.1558 -2.9528 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 2.8242 -6.4465 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0282 -5.4868 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 13.5545 -7.8585 0.0000 O 0 5 0 0 0 0 0 0 0 0 0 0 11.8551 -8.8396 0.0000 O 0 5 0 0 0 0 0 0 0 0 0 0 4.2080 -1.4811 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.8748 -3.8993 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 -4.8981 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 11.8551 -4.9151 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5086 -2.4623 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.6067 -1.4811 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 9.3061 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 11.0054 -1.4811 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.6659 -7.4176 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.0192 -5.7554 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.7570 -5.8962 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.9279 -6.8455 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.6067 -4.4245 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 9.3061 -3.4434 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 11.0054 -3.4434 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.6739 -6.9370 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6291 -4.5905 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 3 2 0 0 0 0 1 9 1 0 0 0 0 2 4 2 0 0 0 0 2 9 1 0 0 0 0 3 11 1 0 0 0 0 4 16 1 0 0 0 0 5 9 2 0 0 0 0 5 12 1 0 0 0 0 6 10 2 0 0 0 0 6 13 1 0 0 0 0 7 15 1 0 0 0 0 7 29 1 0 0 0 0 8 14 1 0 0 0 0 8 44 1 0 0 0 0 10 17 1 0 0 0 0 10 26 1 0 0 0 0 11 12 2 0 0 0 0 11 30 1 0 0 0 0 12 31 1 0 0 0 0 13 19 2 0 0 0 0 13 32 1 0 0 0 0 14 20 1 0 0 0 0 14 45 1 0 0 0 0 15 33 2 0 0 0 0 15 34 1 0 0 0 0 16 35 2 0 0 0 0 16 46 1 0 0 0 0 17 18 1 0 0 0 0 17 23 2 0 0 0 0 18 24 1 0 0 0 0 18 29 1 0 0 0 0 19 23 1 0 0 0 0 19 36 1 0 0 0 0 20 21 1 0 0 0 0 20 37 1 0 0 0 0 21 22 1 0 0 0 0 21 38 1 0 0 0 0 22 27 1 0 0 0 0 22 39 1 0 0 0 0 23 48 1 0 0 0 0 24 25 1 0 0 0 0 24 47 1 0 0 0 0 25 40 2 0 0 0 0 25 41 1 0 0 0 0 26 42 2 0 0 0 0 26 44 1 0 0 0 0 27 45 1 0 0 0 0 27 46 1 0 0 0 0 28 29 1 0 0 0 0 28 43 2 0 0 0 0 28 47 1 0 0 0 0 29 48 1 0 0 0 0 M CHG 2 30 -1 31 -1 M END $$$$

Physi-Chem Properties

Molecular Weight:	676.09
Volume:	600.098
LogP:	-1.304
LogD:	-1.149
LogS:	-2.173
# Rotatable Bonds:	11
TPSA:	319.23
# H-Bond Aceptor:	19
# H-Bond Donor:	7
# Rings:	5
# Heavy Atoms:	19

MedChem Properties

QED Drug-Likeness Score:	0.057
Synthetic Accessibility Score:	5.493
Fsp3:	0.345
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	2
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.456
MDCK Permeability:	5.8488090871833265e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.478
Human Intestinal Absorption (HIA):	0.693
20% Bioavailability (F20%):	0.711
30% Bioavailability (F30%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.033
Plasma Protein Binding (PPB):	85.04833221435547%
Volume Distribution (VD):	0.34
Pgp-substrate:	10.176740646362305%

ADMET: Metabolism

CYP1A2-inhibitor:	0.007
CYP1A2-substrate:	0.004
CYP2C19-inhibitor:	0.012
CYP2C19-substrate:	0.035
CYP2C9-inhibitor:	0.031
CYP2C9-substrate:	0.788
CYP2D6-inhibitor:	0.011
CYP2D6-substrate:	0.065
CYP3A4-inhibitor:	0.053
CYP3A4-substrate:	0.005

ADMET: Excretion

Clearance (CL):	1.816
Half-life (T1/2):	0.938

ADMET: Toxicity

hERG Blockers:	0.012
Human Hepatotoxicity (H-HT):	0.618
Drug-inuced Liver Injury (DILI):	0.95
AMES Toxicity:	0.088
Rat Oral Acute Toxicity:	0.075
Maximum Recommended Daily Dose:	0.002
Skin Sensitization:	0.209
Carcinogencity:	0.053
Eye Corrosion:	0.003
Eye Irritation:	0.209
Respiratory Toxicity:	0.001

Download Data

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

Natural Product: NPC475360

Natural Product ID:	NPC475360
*Common Name:**	Balanophotannin G
IUPAC Name:	dipotassium;(1R,3aR,8bR)-3a-(carboxylatomethyl)-8-[[(2R,3S,4S,5R,6S)-6-[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy-3,4,5-trihydroxyoxan-2-yl]methoxycarbonyl]-5,6-dihydroxy-3-oxo-1,8b-dihydrofuro[3,4-b][1]benzofuran-1-carboxylate
Synonyms:	Balanophotannin G
Standard InCHIKey:	POJLFNLRUDCDSB-DOJHFFIFSA-L
Standard InCHI:	InChI=1S/C29H26O19.2K/c30-11-3-1-9(5-12(11)31)2-4-16(35)46-27-22(39)21(38)20(37)14(45-27)8-44-26(42)10-6-13(32)19(36)23-17(10)18-24(25(40)41)47-28(43)29(18,48-23)7-15(33)34;;/h1-6,14,18,20-22,24,27,30-32,36-39H,7-8H2,(H,33,34)(H,40,41);;/q;2*+1/p-2/b4-2+;;/t14-,18-,20-,21+,22-,24-,27+,29-;;/m1../s1
SMILES:	O=C(O[C@@H]1O[C@H](COC(=O)c2cc(O)c(c3c2[C@@H]2[C@@H](OC(=O)[C@@]2(O3)CC(=O)O)C(=O)O)O)[C@H]([C@@H]([C@H]1O)O)O)/C=C/c1ccc(c(c1)[O-])[O-].[K+].[K+]
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL504285
PubChem CID:	24862053
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
NPO15233	Balanophora japonica	Species	Balanophoraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18302336]
NPO15233	Balanophora japonica	Species	Balanophoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15233	Balanophora japonica	Species	Balanophoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15233	Balanophora japonica	Species	Balanophoraceae	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
IC50	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT65	Cell Line	HepG2	Homo sapiens	IC50	=	18040.0	nM	PMID[474917]

☑ 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 NPC475360 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	442
0.1-0.2	1680
0.2-0.3	3506
0.3-0.4	7927
0.4-0.5	9965
0.5-0.6	5309
0.6-0.7	5890
0.7-0.8	6676
0.8-0.85	1123
0.85-0.9	176
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9474	High Similarity	NPC473713
0.9422	High Similarity	NPC170203
0.9128	High Similarity	NPC72249
0.9017	High Similarity	NPC212748
0.9012	High Similarity	NPC149244
0.9012	High Similarity	NPC48640
0.8971	High Similarity	NPC171706
0.8944	High Similarity	NPC7839
0.8944	High Similarity	NPC173872
0.8944	High Similarity	NPC142291
0.8944	High Similarity	NPC119094
0.892	High Similarity	NPC296018
0.892	High Similarity	NPC268533
0.892	High Similarity	NPC154741
0.8914	High Similarity	NPC4390
0.8908	High Similarity	NPC155763
0.8908	High Similarity	NPC235260
0.8908	High Similarity	NPC20505
0.8902	High Similarity	NPC116745
0.8895	High Similarity	NPC201814
0.8895	High Similarity	NPC165720
0.8889	High Similarity	NPC22324
0.887	High Similarity	NPC476773
0.887	High Similarity	NPC113836
0.887	High Similarity	NPC37668
0.887	High Similarity	NPC253521
0.887	High Similarity	NPC241196
0.8864	High Similarity	NPC49344
0.8864	High Similarity	NPC101191
0.8864	High Similarity	NPC210094
0.8864	High Similarity	NPC253685
0.8864	High Similarity	NPC237435
0.8864	High Similarity	NPC135277
0.8864	High Similarity	NPC43211
0.8864	High Similarity	NPC115760
0.8857	High Similarity	NPC175107
0.8857	High Similarity	NPC476772
0.8857	High Similarity	NPC153755
0.8857	High Similarity	NPC178737
0.8857	High Similarity	NPC235575
0.8857	High Similarity	NPC190003
0.8857	High Similarity	NPC245452
0.8851	High Similarity	NPC138927
0.8851	High Similarity	NPC476771
0.8844	High Similarity	NPC255615
0.8844	High Similarity	NPC254306
0.8844	High Similarity	NPC67037
0.8837	High Similarity	NPC88043
0.8814	High Similarity	NPC211532
0.8814	High Similarity	NPC233994
0.8814	High Similarity	NPC472384
0.8814	High Similarity	NPC472382
0.8814	High Similarity	NPC144097
0.8814	High Similarity	NPC61904
0.8814	High Similarity	NPC472380
0.8814	High Similarity	NPC472385
0.8814	High Similarity	NPC297574
0.8814	High Similarity	NPC198324
0.88	High Similarity	NPC116864
0.88	High Similarity	NPC244776
0.88	High Similarity	NPC206123
0.88	High Similarity	NPC149011
0.88	High Similarity	NPC204937
0.8793	High Similarity	NPC92565
0.8793	High Similarity	NPC42892
0.8793	High Similarity	NPC298847
0.8793	High Similarity	NPC45400
0.8793	High Similarity	NPC160156
0.8786	High Similarity	NPC88243
0.8786	High Similarity	NPC34531
0.8786	High Similarity	NPC475738
0.8779	High Similarity	NPC144557
0.8778	High Similarity	NPC231254
0.8772	High Similarity	NPC239966
0.8772	High Similarity	NPC44507
0.8772	High Similarity	NPC203020
0.8771	High Similarity	NPC208797
0.8771	High Similarity	NPC469371
0.8771	High Similarity	NPC473073
0.8771	High Similarity	NPC53680
0.8771	High Similarity	NPC473071
0.8764	High Similarity	NPC139571
0.8764	High Similarity	NPC293626
0.8764	High Similarity	NPC173837
0.8764	High Similarity	NPC258044
0.8764	High Similarity	NPC196127
0.8764	High Similarity	NPC217520
0.8764	High Similarity	NPC267680
0.8764	High Similarity	NPC35167
0.8764	High Similarity	NPC217387
0.8757	High Similarity	NPC84482
0.8757	High Similarity	NPC169645
0.8757	High Similarity	NPC477848
0.8757	High Similarity	NPC223426
0.8757	High Similarity	NPC264735
0.8757	High Similarity	NPC108202
0.8757	High Similarity	NPC34267
0.8757	High Similarity	NPC81042
0.8757	High Similarity	NPC469354
0.8757	High Similarity	NPC214621
0.875	High Similarity	NPC60735
0.875	High Similarity	NPC26230
0.875	High Similarity	NPC476358
0.875	High Similarity	NPC261254
0.8743	High Similarity	NPC219904
0.8743	High Similarity	NPC223747
0.8743	High Similarity	NPC225434
0.8743	High Similarity	NPC52382
0.8743	High Similarity	NPC120099
0.8743	High Similarity	NPC229687
0.8743	High Similarity	NPC270578
0.8743	High Similarity	NPC203050
0.8736	High Similarity	NPC274618
0.8736	High Similarity	NPC276222
0.8736	High Similarity	NPC308404
0.8736	High Similarity	NPC88789
0.8736	High Similarity	NPC253662
0.8736	High Similarity	NPC145038
0.8736	High Similarity	NPC179950
0.8736	High Similarity	NPC21100
0.8736	High Similarity	NPC118284
0.8736	High Similarity	NPC56077
0.8736	High Similarity	NPC197285
0.8736	High Similarity	NPC281131
0.8729	High Similarity	NPC261623
0.8729	High Similarity	NPC111490
0.8728	High Similarity	NPC223006
0.8728	High Similarity	NPC173729
0.8728	High Similarity	NPC134047
0.8728	High Similarity	NPC272750
0.8722	High Similarity	NPC297503
0.8722	High Similarity	NPC36138
0.8722	High Similarity	NPC470447
0.8722	High Similarity	NPC473072
0.8722	High Similarity	NPC470449
0.8722	High Similarity	NPC35924
0.8722	High Similarity	NPC97119
0.8722	High Similarity	NPC470718
0.8722	High Similarity	NPC135831
0.8722	High Similarity	NPC107987
0.8722	High Similarity	NPC199172
0.8722	High Similarity	NPC470445
0.8722	High Similarity	NPC470446
0.8715	High Similarity	NPC198902
0.8715	High Similarity	NPC212290
0.8715	High Similarity	NPC244903
0.8715	High Similarity	NPC80956
0.8713	High Similarity	NPC160780
0.8713	High Similarity	NPC289811
0.8708	High Similarity	NPC257714
0.8708	High Similarity	NPC89127
0.8708	High Similarity	NPC471669
0.8708	High Similarity	NPC8573
0.8701	High Similarity	NPC34436
0.8701	High Similarity	NPC45522
0.8701	High Similarity	NPC24043
0.8701	High Similarity	NPC101026
0.8701	High Similarity	NPC473550
0.8701	High Similarity	NPC175230
0.8701	High Similarity	NPC42773
0.8701	High Similarity	NPC219600
0.8701	High Similarity	NPC169977
0.8701	High Similarity	NPC166674
0.8701	High Similarity	NPC263119
0.8701	High Similarity	NPC21666
0.8701	High Similarity	NPC474568
0.8701	High Similarity	NPC46640
0.8701	High Similarity	NPC88560
0.8701	High Similarity	NPC172033
0.8693	High Similarity	NPC254855
0.8693	High Similarity	NPC259896
0.8693	High Similarity	NPC471416
0.8693	High Similarity	NPC245014
0.8693	High Similarity	NPC285197
0.8693	High Similarity	NPC136042
0.8693	High Similarity	NPC84265
0.8693	High Similarity	NPC67326
0.8693	High Similarity	NPC156869
0.8693	High Similarity	NPC282987
0.8693	High Similarity	NPC29958
0.8693	High Similarity	NPC34287
0.8693	High Similarity	NPC181778
0.8693	High Similarity	NPC255157
0.8686	High Similarity	NPC173637
0.8686	High Similarity	NPC265530
0.8686	High Similarity	NPC52550
0.8686	High Similarity	NPC84362
0.8686	High Similarity	NPC226304
0.8686	High Similarity	NPC317489
0.8686	High Similarity	NPC325555
0.8686	High Similarity	NPC223424
0.8686	High Similarity	NPC229729
0.8686	High Similarity	NPC127546
0.8681	High Similarity	NPC105591
0.8681	High Similarity	NPC65489
0.8678	High Similarity	NPC55786
0.8678	High Similarity	NPC277205
0.8678	High Similarity	NPC19388
0.8678	High Similarity	NPC240431
0.8674	High Similarity	NPC21359

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 NPC475360 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	366
0.1-0.2	890
0.2-0.3	2005
0.3-0.4	2674
0.4-0.5	1880
0.5-0.6	899
0.6-0.7	298
0.7-0.8	120
0.8-0.85	16
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8902	High Similarity	NPD3818	Discontinued
0.8864	High Similarity	NPD4338	Clinical (unspecified phase)
0.8644	High Similarity	NPD6797	Phase 2
0.8596	High Similarity	NPD7251	Discontinued
0.8547	High Similarity	NPD7808	Phase 3
0.8483	Intermediate Similarity	NPD7472	Approved
0.8483	Intermediate Similarity	NPD7074	Phase 3
0.8427	Intermediate Similarity	NPD7054	Approved
0.8409	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.8391	Intermediate Similarity	NPD6234	Discontinued
0.8382	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8382	Intermediate Similarity	NPD3882	Suspended
0.8371	Intermediate Similarity	NPD7228	Approved
0.8333	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8295	Intermediate Similarity	NPD7199	Phase 2
0.8276	Intermediate Similarity	NPD4965	Approved
0.8276	Intermediate Similarity	NPD4967	Phase 2
0.8276	Intermediate Similarity	NPD4966	Approved
0.8258	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8258	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8258	Intermediate Similarity	NPD6166	Phase 2
0.8232	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8218	Intermediate Similarity	NPD3817	Phase 2
0.8208	Intermediate Similarity	NPD1934	Approved
0.8207	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.8182	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.8161	Intermediate Similarity	NPD1465	Phase 2
0.8125	Intermediate Similarity	NPD7075	Discontinued
0.8122	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8103	Intermediate Similarity	NPD37	Approved
0.8087	Intermediate Similarity	NPD6559	Discontinued
0.8066	Intermediate Similarity	NPD3751	Discontinued
0.8057	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8045	Intermediate Similarity	NPD6232	Discontinued
0.8022	Intermediate Similarity	NPD5844	Phase 1
0.8011	Intermediate Similarity	NPD7473	Discontinued
0.7989	Intermediate Similarity	NPD7685	Pre-registration
0.7989	Intermediate Similarity	NPD7240	Approved
0.7955	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7955	Intermediate Similarity	NPD2801	Approved
0.7933	Intermediate Similarity	NPD5494	Approved
0.791	Intermediate Similarity	NPD5402	Approved
0.7903	Intermediate Similarity	NPD8312	Approved
0.7903	Intermediate Similarity	NPD8313	Approved
0.7898	Intermediate Similarity	NPD6801	Discontinued
0.7874	Intermediate Similarity	NPD1653	Approved
0.7872	Intermediate Similarity	NPD8434	Phase 2
0.7861	Intermediate Similarity	NPD1512	Approved
0.7853	Intermediate Similarity	NPD7819	Suspended
0.7845	Intermediate Similarity	NPD3787	Discontinued
0.7816	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7784	Intermediate Similarity	NPD4380	Phase 2
0.7766	Intermediate Similarity	NPD7435	Discontinued
0.7746	Intermediate Similarity	NPD6799	Approved
0.7746	Intermediate Similarity	NPD1511	Approved
0.7733	Intermediate Similarity	NPD6190	Approved
0.7722	Intermediate Similarity	NPD3749	Approved
0.7714	Intermediate Similarity	NPD5403	Approved
0.7684	Intermediate Similarity	NPD6599	Discontinued
0.7644	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7614	Intermediate Similarity	NPD6777	Approved
0.7614	Intermediate Similarity	NPD6781	Approved
0.7614	Intermediate Similarity	NPD6779	Approved
0.7614	Intermediate Similarity	NPD6780	Approved
0.7614	Intermediate Similarity	NPD6782	Approved
0.7614	Intermediate Similarity	NPD6778	Approved
0.7614	Intermediate Similarity	NPD6776	Approved
0.7609	Intermediate Similarity	NPD3926	Phase 2
0.7604	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.76	Intermediate Similarity	NPD5401	Approved
0.7582	Intermediate Similarity	NPD919	Approved
0.7574	Intermediate Similarity	NPD8151	Discontinued
0.7563	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7558	Intermediate Similarity	NPD1549	Phase 2
0.7542	Intermediate Similarity	NPD7411	Suspended
0.7537	Intermediate Similarity	NPD7874	Approved
0.7537	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7514	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD2534	Approved
0.75	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD2532	Approved
0.75	Intermediate Similarity	NPD1247	Approved
0.75	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7680	Approved
0.75	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD2533	Approved
0.7471	Intermediate Similarity	NPD3750	Approved
0.7463	Intermediate Similarity	NPD8319	Approved
0.7463	Intermediate Similarity	NPD8320	Phase 1
0.7457	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7413	Intermediate Similarity	NPD7698	Approved
0.7413	Intermediate Similarity	NPD7697	Approved
0.7413	Intermediate Similarity	NPD7696	Phase 3
0.7405	Intermediate Similarity	NPD6959	Discontinued
0.7396	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.738	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7376	Intermediate Similarity	NPD7871	Phase 2
0.7376	Intermediate Similarity	NPD7870	Phase 2
0.7371	Intermediate Similarity	NPD4628	Phase 3
0.7363	Intermediate Similarity	NPD8455	Phase 2
0.736	Intermediate Similarity	NPD6534	Approved
0.736	Intermediate Similarity	NPD6535	Approved
0.7358	Intermediate Similarity	NPD5619	Clinical (unspecified phase)
0.7353	Intermediate Similarity	NPD1613	Approved
0.7353	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7353	Intermediate Similarity	NPD7701	Phase 2
0.7333	Intermediate Similarity	NPD3226	Approved
0.733	Intermediate Similarity	NPD7801	Approved
0.733	Intermediate Similarity	NPD7783	Phase 2
0.733	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.732	Intermediate Similarity	NPD8150	Discontinued
0.731	Intermediate Similarity	NPD230	Phase 1
0.7299	Intermediate Similarity	NPD7266	Discontinued
0.7283	Intermediate Similarity	NPD1510	Phase 2
0.7277	Intermediate Similarity	NPD5006	Approved
0.7277	Intermediate Similarity	NPD5005	Approved
0.7273	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD7700	Phase 2
0.725	Intermediate Similarity	NPD7699	Phase 2
0.7241	Intermediate Similarity	NPD2796	Approved
0.7225	Intermediate Similarity	NPD7930	Approved
0.7209	Intermediate Similarity	NPD1933	Approved
0.7207	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7207	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7189	Intermediate Similarity	NPD7768	Phase 2
0.7184	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7184	Intermediate Similarity	NPD3748	Approved
0.7183	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.7178	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7164	Intermediate Similarity	NPD4420	Approved
0.7151	Intermediate Similarity	NPD943	Approved
0.7143	Intermediate Similarity	NPD1551	Phase 2
0.7143	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7119	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7118	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7112	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.711	Intermediate Similarity	NPD6355	Discontinued
0.711	Intermediate Similarity	NPD447	Suspended
0.7108	Intermediate Similarity	NPD6823	Phase 2
0.709	Intermediate Similarity	NPD5710	Approved
0.709	Intermediate Similarity	NPD7229	Phase 3
0.709	Intermediate Similarity	NPD5711	Approved
0.7079	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7076	Intermediate Similarity	NPD3027	Phase 3
0.7059	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7053	Intermediate Similarity	NPD7584	Approved
0.7052	Intermediate Similarity	NPD1240	Approved
0.7052	Intermediate Similarity	NPD7966	Clinical (unspecified phase)
0.7052	Intermediate Similarity	NPD4060	Phase 1
0.7045	Intermediate Similarity	NPD2935	Discontinued
0.7037	Intermediate Similarity	NPD8127	Discontinued
0.7035	Intermediate Similarity	NPD3764	Approved
0.7035	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7033	Intermediate Similarity	NPD920	Approved
0.703	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7022	Intermediate Similarity	NPD6674	Discontinued
0.7019	Intermediate Similarity	NPD7585	Approved
0.7017	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.701	Intermediate Similarity	NPD5953	Discontinued
0.7009	Intermediate Similarity	NPD4111	Phase 1
0.7009	Intermediate Similarity	NPD4665	Approved
0.7006	Intermediate Similarity	NPD2346	Discontinued
0.7	Intermediate Similarity	NPD7296	Approved
0.6995	Remote Similarity	NPD8404	Phase 2
0.6989	Remote Similarity	NPD7033	Discontinued
0.6971	Remote Similarity	NPD7583	Approved
0.6971	Remote Similarity	NPD1607	Approved
0.6963	Remote Similarity	NPD5242	Approved
0.6957	Remote Similarity	NPD7458	Discontinued
0.6952	Remote Similarity	NPD5353	Approved
0.6949	Remote Similarity	NPD6099	Approved
0.6949	Remote Similarity	NPD6100	Approved
0.6944	Remote Similarity	NPD8366	Approved
0.6944	Remote Similarity	NPD7907	Approved
0.6943	Remote Similarity	NPD7799	Discontinued
0.6936	Remote Similarity	NPD6798	Discontinued
0.6927	Remote Similarity	NPD2403	Approved
0.6927	Remote Similarity	NPD2800	Approved
0.691	Remote Similarity	NPD2344	Approved
0.6908	Remote Similarity	NPD4004	Approved
0.6908	Remote Similarity	NPD4002	Approved
0.6906	Remote Similarity	NPD643	Clinical (unspecified phase)
0.69	Remote Similarity	NPD4287	Approved
0.6898	Remote Similarity	NPD5761	Phase 2
0.6898	Remote Similarity	NPD5760	Phase 2
0.6895	Remote Similarity	NPD8491	Approved
0.6893	Remote Similarity	NPD3452	Approved
0.6893	Remote Similarity	NPD2493	Approved
0.6893	Remote Similarity	NPD2799	Discontinued
0.6893	Remote Similarity	NPD2494	Approved
0.6893	Remote Similarity	NPD3450	Approved
0.6888	Remote Similarity	NPD6764	Approved
0.6888	Remote Similarity	NPD6765	Approved
0.6885	Remote Similarity	NPD6273	Approved
0.6881	Remote Similarity	NPD6213	Phase 3
0.6881	Remote Similarity	NPD6212	Phase 3
0.6881	Remote Similarity	NPD6214	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD4582	Approved
0.6875	Remote Similarity	NPD4583	Approved
0.6869	Remote Similarity	NPD8407	Phase 2

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