NPASS Compound

Structure

CID222674 OpenBabel06191716012D 37 40 0 0 1 0 0 0 0 0999 V2000 -2.0000 5.1962 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0000 6.9282 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0000 5.1962 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0000 6.9282 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0000 5.1962 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 6.9282 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5000 6.0622 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5000 6.0622 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5000 6.0622 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0000 6.9282 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5000 4.3301 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5000 6.0622 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5000 6.0622 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5000 0.8660 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.0000 1.7321 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.5000 4.3301 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0000 5.1962 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5000 0.8660 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.0000 1.7321 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.0000 1.7321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5000 2.5981 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.5000 6.0622 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.0000 6.9282 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5000 7.7942 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.0000 3.4641 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.7321 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.5000 0.8660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.5000 2.5981 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 5.1962 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.0000 3.4641 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5000 2.5981 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0 1 3 1 0 0 0 0 1 7 2 0 0 0 0 2 4 2 0 0 0 0 2 7 1 0 0 0 0 3 8 2 0 0 0 0 4 8 1 0 0 0 0 5 9 2 0 0 0 0 5 11 1 0 0 0 0 6 10 1 0 0 0 0 6 12 2 0 0 0 0 7 12 1 0 0 0 0 8 22 1 0 0 0 0 9 13 1 0 0 0 0 9 23 1 0 0 0 0 10 13 1 0 0 0 0 10 24 2 0 0 0 0 11 16 2 0 0 0 0 11 25 1 0 0 0 0 12 33 1 0 0 0 0 13 17 2 0 0 0 0 14 18 1 0 0 0 0 14 19 1 0 0 0 0 14 26 1 1 0 0 0 15 18 1 0 0 0 0 15 21 1 0 0 0 0 15 27 1 1 0 0 0 16 17 1 0 0 0 0 16 34 1 0 0 0 0 17 33 1 0 0 0 0 18 36 1 6 0 0 0 19 20 1 6 0 0 0 19 35 1 0 0 0 0 20 28 2 0 0 0 0 20 29 1 0 0 0 0 21 34 1 6 0 0 0 21 35 1 0 0 0 0 30 37 1 0 0 0 0 31 37 2 0 0 0 0 32 37 2 0 0 0 0 36 37 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	542.04
Volume:	464.181
LogP:	-0.124
LogD:	0.005
LogS:	-1.424
# Rotatable Bonds:	6
TPSA:	250.72
# H-Bond Aceptor:	15
# H-Bond Donor:	7
# Rings:	4
# Heavy Atoms:	16

MedChem Properties

QED Drug-Likeness Score:	0.197
Synthetic Accessibility Score:	4.264
Fsp3:	0.238
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.507
MDCK Permeability:	1.8282913515577093e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.061
Human Intestinal Absorption (HIA):	0.882
20% Bioavailability (F20%):	0.962
30% Bioavailability (F30%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.007
Plasma Protein Binding (PPB):	91.57491302490234%
Volume Distribution (VD):	0.497
Pgp-substrate:	7.942978858947754%

ADMET: Metabolism

CYP1A2-inhibitor:	0.032
CYP1A2-substrate:	0.043
CYP2C19-inhibitor:	0.036
CYP2C19-substrate:	0.035
CYP2C9-inhibitor:	0.016
CYP2C9-substrate:	0.516
CYP2D6-inhibitor:	0.015
CYP2D6-substrate:	0.112
CYP3A4-inhibitor:	0.009
CYP3A4-substrate:	0.0

ADMET: Excretion

Clearance (CL):	0.898
Half-life (T1/2):	0.76

ADMET: Toxicity

hERG Blockers:	0.097
Human Hepatotoxicity (H-HT):	0.632
Drug-inuced Liver Injury (DILI):	0.982
AMES Toxicity:	0.163
Rat Oral Acute Toxicity:	0.105
Maximum Recommended Daily Dose:	0.032
Skin Sensitization:	0.304
Carcinogencity:	0.453
Eye Corrosion:	0.003
Eye Irritation:	0.063
Respiratory Toxicity:	0.97

Download Data

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

Natural Product: NPC222674

Natural Product ID:	NPC222674
*Common Name:**	Theograndin I
IUPAC Name:	(2S,3R,4S,5R,6S)-6-[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxochromen-8-yl]oxy-3,5-dihydroxy-4-sulfooxyoxane-2-carboxylic acid
Synonyms:	Theograndin I
Standard InCHIKey:	RUJCBFMBNQPWBK-DLSLMLROSA-N
Standard InCHI:	InChI=1S/C21H18O15S/c22-8-3-1-7(2-4-8)12-6-10(24)13-9(23)5-11(25)16(17(13)33-12)34-21-15(27)18(36-37(30,31)32)14(26)19(35-21)20(28)29/h1-6,14-15,18-19,21-23,25-27H,(H,28,29)(H,30,31,32)/t14-,15+,18-,19-,21+/m0/s1
SMILES:	OC(=O)[C@H]1O[C@@H](Oc2c(O)cc(c3c2oc(cc3=O)c2ccc(cc2)O)O)[C@@H]([C@H]([C@@H]1O)OS(=O)(=O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL460972
PubChem CID:	11156985
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001111] Flavonoid glycosides [CHEMONTID:0001583] Flavonoid O-glycosides [CHEMONTID:0002934] Flavonoid O-glucuronides [CHEMONTID:0003541] Flavonoid-8-O-glucuronides

*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
NPO28975	Thamnosma rhodesica	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28975	Thamnosma rhodesica	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO29106	Tanacetum argenteum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29403	Ophiopogon chekiangensis	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28975	Thamnosma rhodesica	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29052	Papaver hybridum	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28990	Bidens sulphureus	Species	Asteraceae	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	3

Activity Type	# Activity
Cell Line	2
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT393	Cell Line	HCT-116	Homo sapiens	IC50	=	205000.0	nM	PMID[495734]
NPT660	Cell Line	SW480	Homo sapiens	IC50	=	164000.0	nM	PMID[495734]
NPT1	Others	Radical scavenging activity		IC50	=	341100.0	nM	PMID[495734]

☑ 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 NPC222674 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	459
0.1-0.2	1982
0.2-0.3	4779
0.3-0.4	10258
0.4-0.5	7740
0.5-0.6	4375
0.6-0.7	5655
0.7-0.8	4859
0.8-0.85	1539
0.85-0.9	692
0.9-0.95	298
0.95-1	61

Similarity Score	Similarity Level	Natural Product ID
0.994	High Similarity	NPC107987
0.9759	High Similarity	NPC135277
0.9759	High Similarity	NPC101191
0.9759	High Similarity	NPC210094
0.9759	High Similarity	NPC49344
0.9759	High Similarity	NPC115760
0.9759	High Similarity	NPC237435
0.9759	High Similarity	NPC43211
0.9701	High Similarity	NPC198324
0.9701	High Similarity	NPC472385
0.9641	High Similarity	NPC264735
0.9641	High Similarity	NPC477848
0.9583	High Similarity	NPC268533
0.9583	High Similarity	NPC211532
0.9583	High Similarity	NPC233994
0.9581	High Similarity	NPC4390
0.9581	High Similarity	NPC169977
0.9581	High Similarity	NPC42773
0.9581	High Similarity	NPC21666
0.9581	High Similarity	NPC101026
0.9581	High Similarity	NPC24043
0.9581	High Similarity	NPC45522
0.9578	High Similarity	NPC282987
0.9578	High Similarity	NPC235260
0.9578	High Similarity	NPC20505
0.9578	High Similarity	NPC155763
0.9578	High Similarity	NPC245014
0.9578	High Similarity	NPC84265
0.9521	High Similarity	NPC117260
0.9521	High Similarity	NPC254540
0.9521	High Similarity	NPC476405
0.9521	High Similarity	NPC153755
0.9521	High Similarity	NPC172807
0.9521	High Similarity	NPC211594
0.9521	High Similarity	NPC190003
0.9521	High Similarity	NPC175107
0.9518	High Similarity	NPC138927
0.9474	High Similarity	NPC470445
0.9474	High Similarity	NPC470446
0.9474	High Similarity	NPC36138
0.9474	High Similarity	NPC470449
0.9474	High Similarity	NPC470447
0.9467	High Similarity	NPC472384
0.9467	High Similarity	NPC8573
0.9467	High Similarity	NPC472382
0.9467	High Similarity	NPC472380
0.9461	High Similarity	NPC244776
0.9461	High Similarity	NPC116864
0.9458	High Similarity	NPC45618
0.9458	High Similarity	NPC146792
0.9458	High Similarity	NPC58716
0.9419	High Similarity	NPC470455
0.9419	High Similarity	NPC470416
0.9419	High Similarity	NPC470451
0.9412	High Similarity	NPC168584
0.9408	High Similarity	NPC253685
0.9401	High Similarity	NPC225434
0.9401	High Similarity	NPC203050
0.9401	High Similarity	NPC219904
0.9401	High Similarity	NPC186807
0.9401	High Similarity	NPC58053
0.9401	High Similarity	NPC105025
0.9401	High Similarity	NPC475942
0.9401	High Similarity	NPC226294
0.9401	High Similarity	NPC223747
0.9401	High Similarity	NPC469931
0.9401	High Similarity	NPC45638
0.9401	High Similarity	NPC120099
0.9401	High Similarity	NPC201292
0.9401	High Similarity	NPC93337
0.9398	High Similarity	NPC145038
0.9398	High Similarity	NPC281131
0.9398	High Similarity	NPC21100
0.9398	High Similarity	NPC197285
0.9398	High Similarity	NPC179950
0.9398	High Similarity	NPC253662
0.9398	High Similarity	NPC276222
0.9398	High Similarity	NPC274618
0.9398	High Similarity	NPC118284
0.9398	High Similarity	NPC56077
0.9398	High Similarity	NPC308404
0.9398	High Similarity	NPC88789
0.9357	High Similarity	NPC110941
0.9357	High Similarity	NPC470444
0.9357	High Similarity	NPC241423
0.9357	High Similarity	NPC473571
0.9357	High Similarity	NPC126784
0.9357	High Similarity	NPC473682
0.9357	High Similarity	NPC470443
0.9353	High Similarity	NPC470949
0.9353	High Similarity	NPC65563
0.9353	High Similarity	NPC144097
0.9353	High Similarity	NPC472992
0.9353	High Similarity	NPC169733
0.9353	High Similarity	NPC472991
0.9353	High Similarity	NPC61904
0.9345	High Similarity	NPC206123
0.9341	High Similarity	NPC84362
0.9341	High Similarity	NPC226304
0.9341	High Similarity	NPC325555
0.9341	High Similarity	NPC52550
0.9341	High Similarity	NPC265530
0.9341	High Similarity	NPC173637
0.9341	High Similarity	NPC127546
0.9341	High Similarity	NPC317489
0.9341	High Similarity	NPC223424
0.9337	High Similarity	NPC55786
0.9337	High Similarity	NPC240431
0.9337	High Similarity	NPC19388
0.9337	High Similarity	NPC277205
0.9302	High Similarity	NPC473071
0.9302	High Similarity	NPC473073
0.9298	High Similarity	NPC253521
0.9298	High Similarity	NPC139571
0.9298	High Similarity	NPC35167
0.9298	High Similarity	NPC173837
0.9298	High Similarity	NPC113836
0.9298	High Similarity	NPC37668
0.9298	High Similarity	NPC217520
0.9294	High Similarity	NPC214621
0.9294	High Similarity	NPC34267
0.9294	High Similarity	NPC223426
0.9294	High Similarity	NPC81042
0.929	High Similarity	NPC3583
0.929	High Similarity	NPC307518
0.929	High Similarity	NPC60735
0.929	High Similarity	NPC26230
0.929	High Similarity	NPC472386
0.929	High Similarity	NPC205076
0.929	High Similarity	NPC48773
0.929	High Similarity	NPC259152
0.9286	High Similarity	NPC112755
0.9286	High Similarity	NPC471457
0.9286	High Similarity	NPC170675
0.9281	High Similarity	NPC73855
0.9281	High Similarity	NPC135599
0.9281	High Similarity	NPC328940
0.9281	High Similarity	NPC113968
0.9281	High Similarity	NPC277174
0.9277	High Similarity	NPC191306
0.9277	High Similarity	NPC270335
0.9249	High Similarity	NPC473072
0.924	High Similarity	NPC471669
0.924	High Similarity	NPC296018
0.924	High Similarity	NPC89127
0.924	High Similarity	NPC154741
0.9235	High Similarity	NPC204693
0.9231	High Similarity	NPC471416
0.9231	High Similarity	NPC183357
0.9231	High Similarity	NPC285197
0.9231	High Similarity	NPC22195
0.9231	High Similarity	NPC204937
0.9231	High Similarity	NPC34287
0.9231	High Similarity	NPC105511
0.9231	High Similarity	NPC156869
0.9231	High Similarity	NPC95866
0.9231	High Similarity	NPC29958
0.9231	High Similarity	NPC149011
0.9231	High Similarity	NPC136042
0.9231	High Similarity	NPC21190
0.9231	High Similarity	NPC255157
0.9231	High Similarity	NPC67326
0.9231	High Similarity	NPC254855
0.9231	High Similarity	NPC72249
0.9231	High Similarity	NPC259896
0.9231	High Similarity	NPC224462
0.9226	High Similarity	NPC92565
0.9226	High Similarity	NPC116745
0.9226	High Similarity	NPC160156
0.9222	High Similarity	NPC22832
0.9222	High Similarity	NPC311830
0.9217	High Similarity	NPC77660
0.9217	High Similarity	NPC189142
0.9195	High Similarity	NPC148710
0.9186	High Similarity	NPC476621
0.9186	High Similarity	NPC217387
0.9186	High Similarity	NPC476623
0.9186	High Similarity	NPC476620
0.9186	High Similarity	NPC258044
0.9186	High Similarity	NPC267680
0.9186	High Similarity	NPC476618
0.9186	High Similarity	NPC476619
0.9186	High Similarity	NPC476773
0.9186	High Similarity	NPC476622
0.9186	High Similarity	NPC196127
0.9186	High Similarity	NPC293626
0.9186	High Similarity	NPC477895
0.9181	High Similarity	NPC220173
0.9181	High Similarity	NPC472607
0.9181	High Similarity	NPC16194
0.9181	High Similarity	NPC19108
0.9181	High Similarity	NPC294815
0.9181	High Similarity	NPC473327
0.9181	High Similarity	NPC476472
0.9176	High Similarity	NPC245452
0.9176	High Similarity	NPC203259
0.9176	High Similarity	NPC471748
0.9176	High Similarity	NPC134532
0.9176	High Similarity	NPC33054
0.9176	High Similarity	NPC176740

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 NPC222674 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	406
0.1-0.2	978
0.2-0.3	2133
0.3-0.4	2708
0.4-0.5	1726
0.5-0.6	820
0.6-0.7	236
0.7-0.8	108
0.8-0.85	18
0.85-0.9	14
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9759	High Similarity	NPD4338	Clinical (unspecified phase)
0.9176	High Similarity	NPD6797	Phase 2
0.9123	High Similarity	NPD7251	Discontinued
0.907	High Similarity	NPD7808	Phase 3
0.9059	High Similarity	NPD7054	Approved
0.9006	High Similarity	NPD7472	Approved
0.9	High Similarity	NPD3818	Discontinued
0.8895	High Similarity	NPD7074	Phase 3
0.875	High Similarity	NPD4381	Clinical (unspecified phase)
0.8743	High Similarity	NPD3817	Phase 2
0.8683	High Similarity	NPD2801	Approved
0.8663	High Similarity	NPD6167	Clinical (unspecified phase)
0.8663	High Similarity	NPD6166	Phase 2
0.8663	High Similarity	NPD6168	Clinical (unspecified phase)
0.8631	High Similarity	NPD5402	Approved
0.8621	High Similarity	NPD7804	Clinical (unspecified phase)
0.8512	High Similarity	NPD1934	Approved
0.8471	Intermediate Similarity	NPD3882	Suspended
0.8471	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8373	Intermediate Similarity	NPD1512	Approved
0.8353	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8315	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8314	Intermediate Similarity	NPD7075	Discontinued
0.8274	Intermediate Similarity	NPD1653	Approved
0.8253	Intermediate Similarity	NPD1511	Approved
0.8214	Intermediate Similarity	NPD5403	Approved
0.8187	Intermediate Similarity	NPD6801	Discontinued
0.8176	Intermediate Similarity	NPD4380	Phase 2
0.8162	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.814	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8095	Intermediate Similarity	NPD5401	Approved
0.8066	Intermediate Similarity	NPD6559	Discontinued
0.8036	Intermediate Similarity	NPD6799	Approved
0.8011	Intermediate Similarity	NPD5494	Approved
0.8	Intermediate Similarity	NPD5844	Phase 1
0.7944	Intermediate Similarity	NPD3751	Discontinued
0.7931	Intermediate Similarity	NPD1465	Phase 2
0.7921	Intermediate Similarity	NPD3787	Discontinued
0.7882	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7869	Intermediate Similarity	NPD7685	Pre-registration
0.7821	Intermediate Similarity	NPD6232	Discontinued
0.7811	Intermediate Similarity	NPD6190	Approved
0.7796	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.779	Intermediate Similarity	NPD7473	Discontinued
0.7784	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7784	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7766	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7759	Intermediate Similarity	NPD6599	Discontinued
0.7747	Intermediate Similarity	NPD7228	Approved
0.7744	Intermediate Similarity	NPD7435	Discontinued
0.7738	Intermediate Similarity	NPD1549	Phase 2
0.7727	Intermediate Similarity	NPD7819	Suspended
0.7714	Intermediate Similarity	NPD7411	Suspended
0.7688	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7688	Intermediate Similarity	NPD8313	Approved
0.7688	Intermediate Similarity	NPD8312	Approved
0.7667	Intermediate Similarity	NPD7199	Phase 2
0.7667	Intermediate Similarity	NPD1247	Approved
0.7654	Intermediate Similarity	NPD6234	Discontinued
0.7654	Intermediate Similarity	NPD919	Approved
0.759	Intermediate Similarity	NPD6777	Approved
0.759	Intermediate Similarity	NPD6780	Approved
0.759	Intermediate Similarity	NPD6782	Approved
0.759	Intermediate Similarity	NPD6779	Approved
0.759	Intermediate Similarity	NPD6781	Approved
0.759	Intermediate Similarity	NPD6776	Approved
0.759	Intermediate Similarity	NPD6778	Approved
0.7584	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7571	Intermediate Similarity	NPD37	Approved
0.756	Intermediate Similarity	NPD1510	Phase 2
0.7544	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7542	Intermediate Similarity	NPD4965	Approved
0.7542	Intermediate Similarity	NPD4966	Approved
0.7542	Intermediate Similarity	NPD4967	Phase 2
0.7515	Intermediate Similarity	NPD2796	Approved
0.7512	Intermediate Similarity	NPD7874	Approved
0.7512	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7473	Intermediate Similarity	NPD6959	Discontinued
0.7471	Intermediate Similarity	NPD7266	Discontinued
0.7471	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7446	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7442	Intermediate Similarity	NPD3750	Approved
0.7436	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7427	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7425	Intermediate Similarity	NPD1613	Approved
0.7425	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7414	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7403	Intermediate Similarity	NPD3749	Approved
0.7391	Intermediate Similarity	NPD3926	Phase 2
0.7389	Intermediate Similarity	NPD7783	Phase 2
0.7389	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7387	Intermediate Similarity	NPD7698	Approved
0.7387	Intermediate Similarity	NPD7697	Approved
0.7387	Intermediate Similarity	NPD7696	Phase 3
0.7381	Intermediate Similarity	NPD1933	Approved
0.7381	Intermediate Similarity	NPD230	Phase 1
0.7376	Intermediate Similarity	NPD8151	Discontinued
0.735	Intermediate Similarity	NPD7870	Phase 2
0.735	Intermediate Similarity	NPD7871	Phase 2
0.7333	Intermediate Similarity	NPD6534	Approved
0.7333	Intermediate Similarity	NPD6535	Approved
0.7333	Intermediate Similarity	NPD8455	Phase 2
0.7327	Intermediate Similarity	NPD7701	Phase 2
0.7321	Intermediate Similarity	NPD943	Approved
0.731	Intermediate Similarity	NPD1551	Phase 2
0.731	Intermediate Similarity	NPD2935	Discontinued
0.7302	Intermediate Similarity	NPD7240	Approved
0.7278	Intermediate Similarity	NPD447	Suspended
0.7277	Intermediate Similarity	NPD7584	Approved
0.7253	Intermediate Similarity	NPD7768	Phase 2
0.7249	Intermediate Similarity	NPD5953	Discontinued
0.7241	Intermediate Similarity	NPD4628	Phase 3
0.7222	Intermediate Similarity	NPD7700	Phase 2
0.7222	Intermediate Similarity	NPD7699	Phase 2
0.722	Intermediate Similarity	NPD7801	Approved
0.7219	Intermediate Similarity	NPD1240	Approved
0.7202	Intermediate Similarity	NPD8150	Discontinued
0.7202	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7202	Intermediate Similarity	NPD8434	Phase 2
0.7186	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7178	Intermediate Similarity	NPD8320	Phase 1
0.7178	Intermediate Similarity	NPD8319	Approved
0.7175	Intermediate Similarity	NPD2534	Approved
0.7175	Intermediate Similarity	NPD2533	Approved
0.7175	Intermediate Similarity	NPD2532	Approved
0.7164	Intermediate Similarity	NPD6823	Phase 2
0.716	Intermediate Similarity	NPD6233	Phase 2
0.7156	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD3748	Approved
0.7143	Intermediate Similarity	NPD3027	Phase 3
0.7135	Intermediate Similarity	NPD1607	Approved
0.7126	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD920	Approved
0.7086	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7079	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7079	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7074	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD7585	Approved
0.7059	Intermediate Similarity	NPD7211	Clinical (unspecified phase)
0.7053	Intermediate Similarity	NPD7286	Phase 2
0.7044	Intermediate Similarity	NPD7680	Approved
0.7024	Intermediate Similarity	NPD7583	Approved
0.7017	Intermediate Similarity	NPD3226	Approved
0.7015	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7009	Intermediate Similarity	NPD5619	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD2313	Discontinued
0.7	Intermediate Similarity	NPD6798	Discontinued
0.6995	Remote Similarity	NPD6844	Discontinued
0.6989	Remote Similarity	NPD1652	Phase 2
0.698	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD4062	Phase 3
0.6954	Remote Similarity	NPD7033	Discontinued
0.6935	Remote Similarity	NPD6214	Clinical (unspecified phase)
0.6935	Remote Similarity	NPD6213	Phase 3
0.6935	Remote Similarity	NPD6212	Phase 3
0.6923	Remote Similarity	NPD7458	Discontinued
0.6919	Remote Similarity	NPD5353	Approved
0.6905	Remote Similarity	NPD1203	Approved
0.6893	Remote Similarity	NPD1243	Approved
0.6893	Remote Similarity	NPD2800	Approved
0.6882	Remote Similarity	NPD6832	Phase 2
0.6879	Remote Similarity	NPD6355	Discontinued
0.6875	Remote Similarity	NPD2346	Discontinued
0.6867	Remote Similarity	NPD1091	Approved
0.6857	Remote Similarity	NPD2799	Discontinued
0.6842	Remote Similarity	NPD5242	Approved
0.6831	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD5006	Approved
0.6829	Remote Similarity	NPD5005	Approved
0.6826	Remote Similarity	NPD9269	Phase 2
0.6824	Remote Similarity	NPD9494	Approved
0.6821	Remote Similarity	NPD7549	Discontinued
0.6821	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6816	Remote Similarity	NPD4360	Phase 2
0.6816	Remote Similarity	NPD4363	Phase 3
0.6798	Remote Similarity	NPD6674	Discontinued
0.6789	Remote Similarity	NPD5711	Approved
0.6789	Remote Similarity	NPD7229	Phase 3
0.6789	Remote Similarity	NPD5710	Approved
0.6782	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6782	Remote Similarity	NPD5124	Phase 1
0.6782	Remote Similarity	NPD4340	Discontinued
0.6782	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.676	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD6385	Approved
0.6757	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD6386	Approved
0.6751	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6746	Remote Similarity	NPD3225	Approved
0.6737	Remote Similarity	NPD8127	Discontinued
0.6724	Remote Similarity	NPD4060	Phase 1
0.6723	Remote Similarity	NPD6099	Approved
0.6723	Remote Similarity	NPD6100	Approved
0.6716	Remote Similarity	NPD4420	Approved
0.6714	Remote Similarity	NPD7930	Approved
0.6705	Remote Similarity	NPD3268	Approved
0.6705	Remote Similarity	NPD1296	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