NPASS Compound

Structure

NPC475246 OpenBabel07101718282D 41 45 0 0 1 0 0 0 0 0999 V2000 -0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -3.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.9282 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.4641 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -4.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5981 -4.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7321 -4.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7321 -3.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7321 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -5.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 8 1 0 0 0 0 3 4 2 0 0 0 0 3 10 1 0 0 0 0 4 11 1 0 0 0 0 5 10 2 0 0 0 0 5 12 1 0 0 0 0 6 13 2 0 0 0 0 6 14 1 0 0 0 0 7 28 1 0 0 0 0 8 14 2 0 0 0 0 8 17 1 0 0 0 0 9 2 1 6 0 0 0 9 18 1 0 0 0 0 9 38 1 0 0 0 0 10 29 1 0 0 0 0 11 12 2 0 0 0 0 11 20 1 0 0 0 0 12 19 1 0 0 0 0 13 16 1 0 0 0 0 13 19 1 0 0 0 0 14 39 1 0 0 0 0 15 7 1 6 0 0 0 15 21 1 0 0 0 0 15 40 1 0 0 0 0 16 17 2 0 0 0 0 16 20 1 0 0 0 0 17 30 1 0 0 0 0 18 22 1 0 0 0 0 18 31 1 1 0 0 0 19 32 2 0 0 0 0 20 33 2 0 0 0 0 21 23 1 0 0 0 0 21 34 1 1 0 0 0 22 24 1 0 0 0 0 22 35 1 6 0 0 0 23 25 1 0 0 0 0 23 36 1 6 0 0 0 24 26 1 0 0 0 0 24 37 1 6 0 0 0 25 27 1 0 0 0 0 25 41 1 1 0 0 0 26 38 1 0 0 0 0 26 41 1 6 0 0 0 27 39 1 6 0 0 0 27 40 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	578.16
Volume:	534.737
LogP:	1.133
LogD:	0.296
LogS:	-3.357
# Rotatable Bonds:	5
TPSA:	232.9
# H-Bond Aceptor:	14
# H-Bond Donor:	8
# Rings:	5
# Heavy Atoms:	14

MedChem Properties

QED Drug-Likeness Score:	0.167
Synthetic Accessibility Score:	4.683
Fsp3:	0.481
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.452
MDCK Permeability:	1.8387918316875584e-05
Pgp-inhibitor:	0.828
Pgp-substrate:	0.966
Human Intestinal Absorption (HIA):	0.837
20% Bioavailability (F20%):	0.004
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.093
Plasma Protein Binding (PPB):	91.53166961669922%
Volume Distribution (VD):	0.76
Pgp-substrate:	4.064772129058838%

ADMET: Metabolism

CYP1A2-inhibitor:	0.039
CYP1A2-substrate:	0.048
CYP2C19-inhibitor:	0.02
CYP2C19-substrate:	0.057
CYP2C9-inhibitor:	0.006
CYP2C9-substrate:	0.062
CYP2D6-inhibitor:	0.034
CYP2D6-substrate:	0.121
CYP3A4-inhibitor:	0.047
CYP3A4-substrate:	0.049

ADMET: Excretion

Clearance (CL):	2.099
Half-life (T1/2):	0.421

ADMET: Toxicity

hERG Blockers:	0.253
Human Hepatotoxicity (H-HT):	0.082
Drug-inuced Liver Injury (DILI):	0.928
AMES Toxicity:	0.871
Rat Oral Acute Toxicity:	0.018
Maximum Recommended Daily Dose:	0.004
Skin Sensitization:	0.054
Carcinogencity:	0.563
Eye Corrosion:	0.003
Eye Irritation:	0.193
Respiratory Toxicity:	0.009

Download Data

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

Natural Product: NPC475246

Natural Product ID:	NPC475246
*Common Name:**	2-Methyl-1,3,6-Trihydroxyl-9,10-Anthraquinone 3-O-Alpha-Rhamnosyl(1->2)Glucoside
IUPAC Name:	3-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3S,4S,5S,6R)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-1,6-dihydroxy-2-methylanthracene-9,10-dione
Synonyms:
Standard InCHIKey:	UMBHTGLJTANWCB-YORKFUMESA-N
Standard InCHI:	InChI=1S/C27H30O14/c1-8-14(6-13-16(17(8)30)20(33)11-4-3-10(29)5-12(11)19(13)32)39-27-25(23(36)21(34)15(7-28)40-27)41-26-24(37)22(35)18(31)9(2)38-26/h3-6,9,15,18,21-31,34-37H,7H2,1-2H3/t9-,15-,18-,21-,22+,23+,24+,25-,26+,27-/m1/s1
SMILES:	OC[C@H]1O[C@@H](Oc2cc3C(=O)c4cc(O)ccc4C(=O)c3c(c2C)O)[C@@H]([C@H]([C@@H]1O)O)O[C@@H]1O[C@H](C)[C@H]([C@@H]([C@@H]1O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL501915
PubChem CID:	44575695
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000018] Anthracenes [CHEMONTID:0000151] Anthraquinones [CHEMONTID:0001598] Hydroxyanthraquinones

*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
NPO28159	Rubia akane	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8176404]
NPO28159	Rubia akane	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO28159	Rubia akane	Species	Rubiaceae	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	4

Activity Type	# Activity
CELL-LINE	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20967	CELL-LINE	Platelet	n.a.	Activity	=	87.0	%	PMID[522437]
NPT20967	CELL-LINE	Platelet	n.a.	Activity	=	83.4	%	PMID[522437]
NPT20967	CELL-LINE	Platelet	n.a.	Activity	=	84.0	%	PMID[522437]
NPT20967	CELL-LINE	Platelet	n.a.	Activity	=	89.4	%	PMID[522437]

☑ 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 NPC475246 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	1684
0.2-0.3	3519
0.3-0.4	8472
0.4-0.5	9061
0.5-0.6	5117
0.6-0.7	5246
0.7-0.8	6392
0.8-0.85	1978
0.85-0.9	694
0.9-0.95	85
0.95-1	15

Similarity Score	Similarity Level	Natural Product ID
0.9939	High Similarity	NPC3718
0.9878	High Similarity	NPC46958
0.9819	High Similarity	NPC477860
0.9819	High Similarity	NPC475161
0.9816	High Similarity	NPC30432
0.9816	High Similarity	NPC111536
0.9816	High Similarity	NPC271385
0.9816	High Similarity	NPC76128
0.9816	High Similarity	NPC5029
0.9759	High Similarity	NPC153578
0.9759	High Similarity	NPC114257
0.9759	High Similarity	NPC277710
0.9759	High Similarity	NPC299149
0.9697	High Similarity	NPC68381
0.9693	High Similarity	NPC222455
0.9645	High Similarity	NPC87583
0.9639	High Similarity	NPC475233
0.9524	High Similarity	NPC212290
0.9518	High Similarity	NPC85368
0.9518	High Similarity	NPC98776
0.9518	High Similarity	NPC213052
0.9515	High Similarity	NPC298778
0.9474	High Similarity	NPC105591
0.9461	High Similarity	NPC146803
0.9455	High Similarity	NPC259905
0.9451	High Similarity	NPC178851
0.9401	High Similarity	NPC199357
0.9401	High Similarity	NPC203751
0.9401	High Similarity	NPC472054
0.9387	High Similarity	NPC101116
0.9387	High Similarity	NPC278329
0.9387	High Similarity	NPC146837
0.9387	High Similarity	NPC212099
0.9353	High Similarity	NPC315221
0.9345	High Similarity	NPC63105
0.9345	High Similarity	NPC474345
0.9298	High Similarity	NPC313452
0.9294	High Similarity	NPC245059
0.9294	High Similarity	NPC84494
0.929	High Similarity	NPC102053
0.929	High Similarity	NPC289876
0.9277	High Similarity	NPC63470
0.9273	High Similarity	NPC478022
0.9273	High Similarity	NPC178281
0.9273	High Similarity	NPC478020
0.9268	High Similarity	NPC216752
0.9268	High Similarity	NPC44947
0.9264	High Similarity	NPC472320
0.924	High Similarity	NPC164047
0.924	High Similarity	NPC470453
0.924	High Similarity	NPC470448
0.924	High Similarity	NPC470452
0.9231	High Similarity	NPC470454
0.9231	High Similarity	NPC199533
0.9212	High Similarity	NPC257566
0.9212	High Similarity	NPC124155
0.9207	High Similarity	NPC47923
0.9207	High Similarity	NPC303913
0.9191	High Similarity	NPC229817
0.9191	High Similarity	NPC475352
0.9191	High Similarity	NPC473686
0.9191	High Similarity	NPC475220
0.9191	High Similarity	NPC221140
0.9186	High Similarity	NPC293227
0.9186	High Similarity	NPC473631
0.9186	High Similarity	NPC475662
0.9186	High Similarity	NPC473717
0.9181	High Similarity	NPC58538
0.9167	High Similarity	NPC150767
0.9167	High Similarity	NPC78734
0.9152	High Similarity	NPC259834
0.9152	High Similarity	NPC190450
0.9146	High Similarity	NPC271479
0.9141	High Similarity	NPC23817
0.9128	High Similarity	NPC197357
0.9128	High Similarity	NPC85316
0.9112	High Similarity	NPC256760
0.9107	High Similarity	NPC473202
0.9107	High Similarity	NPC246274
0.9107	High Similarity	NPC229687
0.9102	High Similarity	NPC178173
0.9102	High Similarity	NPC70441
0.9091	High Similarity	NPC264302
0.9085	High Similarity	NPC73511
0.9085	High Similarity	NPC308265
0.908	High Similarity	NPC170475
0.908	High Similarity	NPC206378
0.908	High Similarity	NPC241847
0.9059	High Similarity	NPC208668
0.9059	High Similarity	NPC154986
0.9059	High Similarity	NPC168789
0.9053	High Similarity	NPC478021
0.9053	High Similarity	NPC241874
0.9053	High Similarity	NPC76047
0.9053	High Similarity	NPC218488
0.9053	High Similarity	NPC51326
0.9053	High Similarity	NPC231194
0.9053	High Similarity	NPC44558
0.9048	High Similarity	NPC249977
0.9048	High Similarity	NPC45400
0.9048	High Similarity	NPC477502
0.9042	High Similarity	NPC99216
0.904	High Similarity	NPC470199
0.904	High Similarity	NPC314459
0.9036	High Similarity	NPC131745
0.9036	High Similarity	NPC472876
0.9034	High Similarity	NPC314672
0.903	High Similarity	NPC142860
0.903	High Similarity	NPC97285
0.903	High Similarity	NPC271270
0.903	High Similarity	NPC328093
0.903	High Similarity	NPC246469
0.9024	High Similarity	NPC473512
0.9024	High Similarity	NPC129827
0.9024	High Similarity	NPC156457
0.9024	High Similarity	NPC161749
0.9024	High Similarity	NPC197896
0.9024	High Similarity	NPC44931
0.9024	High Similarity	NPC313163
0.9024	High Similarity	NPC258035
0.9024	High Similarity	NPC65003
0.9023	High Similarity	NPC224557
0.9023	High Similarity	NPC292706
0.9018	High Similarity	NPC97052
0.9018	High Similarity	NPC99233
0.9018	High Similarity	NPC39351
0.9018	High Similarity	NPC26195
0.9018	High Similarity	NPC169248
0.9018	High Similarity	NPC72649
0.9012	High Similarity	NPC472387
0.9006	High Similarity	NPC294629
0.9006	High Similarity	NPC223735
0.9006	High Similarity	NPC186800
0.9006	High Similarity	NPC108202
0.9006	High Similarity	NPC307754
0.9006	High Similarity	NPC470667
0.9	High Similarity	NPC294501
0.9	High Similarity	NPC267254
0.9	High Similarity	NPC315619
0.9	High Similarity	NPC67134
0.9	High Similarity	NPC47140
0.9	High Similarity	NPC301683
0.8994	High Similarity	NPC472381
0.8994	High Similarity	NPC472383
0.8994	High Similarity	NPC470206
0.8994	High Similarity	NPC470207
0.8994	High Similarity	NPC61791
0.8994	High Similarity	NPC5319
0.8994	High Similarity	NPC293629
0.8994	High Similarity	NPC43587
0.8988	High Similarity	NPC236934
0.8988	High Similarity	NPC115674
0.8988	High Similarity	NPC210073
0.8988	High Similarity	NPC5778
0.8982	High Similarity	NPC179198
0.8982	High Similarity	NPC29830
0.8982	High Similarity	NPC66087
0.8982	High Similarity	NPC183672
0.8982	High Similarity	NPC278419
0.8977	High Similarity	NPC205721
0.897	High Similarity	NPC22062
0.897	High Similarity	NPC138811
0.897	High Similarity	NPC473634
0.897	High Similarity	NPC53139
0.8966	High Similarity	NPC132111
0.8963	High Similarity	NPC261866
0.8963	High Similarity	NPC78492
0.8963	High Similarity	NPC45165
0.8963	High Similarity	NPC208152
0.8957	High Similarity	NPC106625
0.8953	High Similarity	NPC324220
0.8953	High Similarity	NPC312630
0.8947	High Similarity	NPC236191
0.8947	High Similarity	NPC239549
0.8947	High Similarity	NPC51774
0.8947	High Similarity	NPC25724
0.8941	High Similarity	NPC474434
0.8941	High Similarity	NPC199079
0.8941	High Similarity	NPC177731
0.8941	High Similarity	NPC34287
0.8941	High Similarity	NPC471416
0.8941	High Similarity	NPC105095
0.8941	High Similarity	NPC79056
0.8941	High Similarity	NPC210808
0.8941	High Similarity	NPC105511
0.8941	High Similarity	NPC21190
0.8941	High Similarity	NPC183357
0.8941	High Similarity	NPC22195
0.8941	High Similarity	NPC44328
0.8939	High Similarity	NPC470194
0.8939	High Similarity	NPC470193
0.8939	High Similarity	NPC470198
0.8939	High Similarity	NPC470195
0.8939	High Similarity	NPC470196
0.8939	High Similarity	NPC470200
0.8939	High Similarity	NPC470197
0.8939	High Similarity	NPC282474
0.8939	High Similarity	NPC316274
0.8935	High Similarity	NPC225419
0.8935	High Similarity	NPC93099

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 NPC475246 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	382
0.1-0.2	923
0.2-0.3	1773
0.3-0.4	2676
0.4-0.5	1928
0.5-0.6	949
0.6-0.7	349
0.7-0.8	111
0.8-0.85	41
0.85-0.9	18
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9024	High Similarity	NPD4381	Clinical (unspecified phase)
0.8994	High Similarity	NPD7804	Clinical (unspecified phase)
0.8941	High Similarity	NPD7074	Phase 3
0.892	High Similarity	NPD7879	Clinical (unspecified phase)
0.8882	High Similarity	NPD7054	Approved
0.8862	High Similarity	NPD6959	Discontinued
0.8844	High Similarity	NPD8312	Approved
0.8844	High Similarity	NPD8313	Approved
0.8837	High Similarity	NPD6559	Discontinued
0.883	High Similarity	NPD7472	Approved
0.8779	High Similarity	NPD6797	Phase 2
0.8728	High Similarity	NPD7251	Discontinued
0.8713	High Similarity	NPD3818	Discontinued
0.8678	High Similarity	NPD7808	Phase 3
0.8659	High Similarity	NPD4380	Phase 2
0.8596	High Similarity	NPD6166	Phase 2
0.8596	High Similarity	NPD6168	Clinical (unspecified phase)
0.8596	High Similarity	NPD6167	Clinical (unspecified phase)
0.8579	High Similarity	NPD6780	Approved
0.8579	High Similarity	NPD6779	Approved
0.8579	High Similarity	NPD6777	Approved
0.8579	High Similarity	NPD6778	Approved
0.8579	High Similarity	NPD6781	Approved
0.8579	High Similarity	NPD6776	Approved
0.8579	High Similarity	NPD6782	Approved
0.8511	High Similarity	NPD8151	Discontinued
0.8503	High Similarity	NPD2393	Clinical (unspecified phase)
0.8503	High Similarity	NPD7819	Suspended
0.848	Intermediate Similarity	NPD6232	Discontinued
0.8466	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8462	Intermediate Similarity	NPD7075	Discontinued
0.8448	Intermediate Similarity	NPD5844	Phase 1
0.8441	Intermediate Similarity	NPD7698	Approved
0.8441	Intermediate Similarity	NPD7697	Approved
0.8441	Intermediate Similarity	NPD7435	Discontinued
0.8441	Intermediate Similarity	NPD7696	Phase 3
0.8439	Intermediate Similarity	NPD7473	Discontinued
0.836	Intermediate Similarity	NPD7701	Phase 2
0.8343	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8333	Intermediate Similarity	NPD1934	Approved
0.8306	Intermediate Similarity	NPD6534	Approved
0.8306	Intermediate Similarity	NPD6535	Approved
0.8298	Intermediate Similarity	NPD7871	Phase 2
0.8298	Intermediate Similarity	NPD7870	Phase 2
0.8294	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8286	Intermediate Similarity	NPD3751	Discontinued
0.8284	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8274	Intermediate Similarity	NPD7411	Suspended
0.827	Intermediate Similarity	NPD7700	Phase 2
0.827	Intermediate Similarity	NPD7699	Phase 2
0.8256	Intermediate Similarity	NPD5494	Approved
0.8229	Intermediate Similarity	NPD7783	Phase 2
0.8229	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.8225	Intermediate Similarity	NPD6801	Discontinued
0.8191	Intermediate Similarity	NPD6823	Phase 2
0.8187	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.8182	Intermediate Similarity	NPD7228	Approved
0.8177	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.8177	Intermediate Similarity	NPD7874	Approved
0.8171	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8155	Intermediate Similarity	NPD3226	Approved
0.8146	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8135	Intermediate Similarity	NPD7801	Approved
0.8133	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8133	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8105	Intermediate Similarity	NPD8320	Phase 1
0.8105	Intermediate Similarity	NPD8319	Approved
0.8098	Intermediate Similarity	NPD1549	Phase 2
0.807	Intermediate Similarity	NPD2801	Approved
0.8057	Intermediate Similarity	NPD3787	Discontinued
0.8054	Intermediate Similarity	NPD6213	Phase 3
0.8054	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.8054	Intermediate Similarity	NPD6212	Phase 3
0.8037	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8037	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8024	Intermediate Similarity	NPD2532	Approved
0.8024	Intermediate Similarity	NPD2534	Approved
0.8024	Intermediate Similarity	NPD2533	Approved
0.8023	Intermediate Similarity	NPD5402	Approved
0.8	Intermediate Similarity	NPD6599	Discontinued
0.7977	Intermediate Similarity	NPD3882	Suspended
0.7965	Intermediate Similarity	NPD1465	Phase 2
0.7965	Intermediate Similarity	NPD8455	Phase 2
0.7931	Intermediate Similarity	NPD3749	Approved
0.7919	Intermediate Similarity	NPD3817	Phase 2
0.7914	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7907	Intermediate Similarity	NPD37	Approved
0.7886	Intermediate Similarity	NPD6234	Discontinued
0.788	Intermediate Similarity	NPD8150	Discontinued
0.7874	Intermediate Similarity	NPD4967	Phase 2
0.7874	Intermediate Similarity	NPD4966	Approved
0.7874	Intermediate Similarity	NPD4965	Approved
0.7874	Intermediate Similarity	NPD7768	Phase 2
0.7866	Intermediate Similarity	NPD2796	Approved
0.7857	Intermediate Similarity	NPD1511	Approved
0.7857	Intermediate Similarity	NPD6799	Approved
0.7857	Intermediate Similarity	NPD7390	Discontinued
0.7836	Intermediate Similarity	NPD7458	Discontinued
0.7824	Intermediate Similarity	NPD5403	Approved
0.7818	Intermediate Similarity	NPD2346	Discontinued
0.7805	Intermediate Similarity	NPD1510	Phase 2
0.7802	Intermediate Similarity	NPD7240	Approved
0.7797	Intermediate Similarity	NPD7199	Phase 2
0.7791	Intermediate Similarity	NPD1607	Approved
0.7784	Intermediate Similarity	NPD3750	Approved
0.7784	Intermediate Similarity	NPD4628	Phase 3
0.7772	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.7765	Intermediate Similarity	NPD1512	Approved
0.7744	Intermediate Similarity	NPD7584	Approved
0.7733	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.773	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7706	Intermediate Similarity	NPD5401	Approved
0.7692	Intermediate Similarity	NPD7211	Clinical (unspecified phase)
0.7679	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7669	Intermediate Similarity	NPD1240	Approved
0.7665	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7616	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7611	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7585	Intermediate Similarity	NPD8059	Phase 3
0.7585	Intermediate Similarity	NPD8058	Clinical (unspecified phase)
0.7556	Intermediate Similarity	NPD5711	Approved
0.7556	Intermediate Similarity	NPD5710	Approved
0.7554	Intermediate Similarity	NPD5953	Discontinued
0.7545	Intermediate Similarity	NPD1551	Phase 2
0.7545	Intermediate Similarity	NPD2935	Discontinued
0.7515	Intermediate Similarity	NPD2800	Approved
0.7515	Intermediate Similarity	NPD6674	Discontinued
0.7514	Intermediate Similarity	NPD7685	Pre-registration
0.75	Intermediate Similarity	NPD8434	Phase 2
0.75	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD3748	Approved
0.7471	Intermediate Similarity	NPD1653	Approved
0.7461	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.744	Intermediate Similarity	NPD6100	Approved
0.744	Intermediate Similarity	NPD6099	Approved
0.7436	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7418	Intermediate Similarity	NPD3926	Phase 2
0.7414	Intermediate Similarity	NPD920	Approved
0.7385	Intermediate Similarity	NPD8285	Discontinued
0.7385	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7381	Intermediate Similarity	NPD2799	Discontinued
0.7368	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7351	Intermediate Similarity	NPD7286	Phase 2
0.735	Intermediate Similarity	NPD7585	Approved
0.7337	Intermediate Similarity	NPD5405	Approved
0.7337	Intermediate Similarity	NPD5406	Approved
0.7337	Intermediate Similarity	NPD5408	Approved
0.7337	Intermediate Similarity	NPD5404	Approved
0.7333	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7323	Intermediate Similarity	NPD7680	Approved
0.7308	Intermediate Similarity	NPD1247	Approved
0.73	Intermediate Similarity	NPD7583	Approved
0.7299	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7299	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7294	Intermediate Similarity	NPD2344	Approved
0.7294	Intermediate Similarity	NPD7266	Discontinued
0.7293	Intermediate Similarity	NPD919	Approved
0.7287	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD4625	Phase 3
0.7268	Intermediate Similarity	NPD4360	Phase 2
0.7268	Intermediate Similarity	NPD7229	Phase 3
0.7268	Intermediate Similarity	NPD4363	Phase 3
0.7267	Intermediate Similarity	NPD7003	Approved
0.7257	Intermediate Similarity	NPD6273	Approved
0.7246	Intermediate Similarity	NPD943	Approved
0.7246	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7246	Intermediate Similarity	NPD1613	Approved
0.7241	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7239	Intermediate Similarity	NPD1470	Approved
0.7229	Intermediate Similarity	NPD2313	Discontinued
0.7229	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.722	Intermediate Similarity	NPD7930	Approved
0.7212	Intermediate Similarity	NPD4908	Phase 1
0.7209	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7209	Intermediate Similarity	NPD1243	Approved
0.7204	Intermediate Similarity	NPD7177	Discontinued
0.7184	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD6651	Approved
0.7126	Intermediate Similarity	NPD6190	Approved
0.7126	Intermediate Similarity	NPD2309	Approved
0.7118	Intermediate Similarity	NPD7097	Phase 1
0.7109	Intermediate Similarity	NPD5619	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD1933	Approved
0.7101	Intermediate Similarity	NPD230	Phase 1
0.7095	Intermediate Similarity	NPD8366	Approved
0.7091	Intermediate Similarity	NPD2798	Approved
0.7076	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7072	Intermediate Similarity	NPD5761	Phase 2
0.7072	Intermediate Similarity	NPD5760	Phase 2
0.7062	Intermediate Similarity	NPD4287	Approved
0.7056	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD4060	Phase 1
0.7027	Intermediate Similarity	NPD8127	Discontinued
0.7021	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7017	Intermediate Similarity	NPD6844	Discontinued
0.7006	Intermediate Similarity	NPD6832	Phase 2
0.7006	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD5124	Phase 1
0.7	Intermediate Similarity	NPD447	Suspended

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