NPASS Compound

Structure

CID220167 OpenBabel06191716012D 23 25 0 0 1 0 0 0 0 0999 V2000 -4.2072 1.6691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8005 2.5827 0.0000 C 0 0 0 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 -2.1369 3.2213 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 -3.4641 1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.8060 2.4781 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 -2.5981 1.5000 0.0000 C 0 0 1 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 1.7321 1.0000 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 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.4459 4.1723 0.0000 O 0 0 0 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 2.5981 -0.5000 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 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 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 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 0 0 0 2 8 2 0 0 0 0 3 4 2 0 0 0 0 3 7 1 0 0 0 0 4 21 1 0 0 0 0 5 8 1 0 0 0 0 5 16 1 0 0 0 0 6 17 1 0 0 0 0 7 1 1 1 0 0 0 7 10 1 0 0 0 0 9 6 1 1 0 0 0 9 11 1 0 0 0 0 9 22 1 0 0 0 0 10 8 1 1 0 0 0 10 14 1 0 0 0 0 11 12 1 0 0 0 0 11 18 1 6 0 0 0 12 13 1 0 0 0 0 12 19 1 1 0 0 0 13 15 1 0 0 0 0 13 20 1 6 0 0 0 14 21 1 0 0 0 0 14 23 1 6 0 0 0 15 22 1 0 0 0 0 15 23 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	330.13
Volume:	307.376
LogP:	-0.767
LogD:	-0.219
LogS:	-0.926
# Rotatable Bonds:	4
TPSA:	128.84
# H-Bond Aceptor:	8
# H-Bond Donor:	5
# Rings:	3
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.383
Synthetic Accessibility Score:	4.769
Fsp3:	0.733
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.605
MDCK Permeability:	0.00011228569928789511
Pgp-inhibitor:	0.001
Pgp-substrate:	0.054
Human Intestinal Absorption (HIA):	0.55
20% Bioavailability (F20%):	0.018
30% Bioavailability (F30%):	0.958

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.249
Plasma Protein Binding (PPB):	24.548694610595703%
Volume Distribution (VD):	0.456
Pgp-substrate:	51.380123138427734%

ADMET: Metabolism

CYP1A2-inhibitor:	0.017
CYP1A2-substrate:	0.037
CYP2C19-inhibitor:	0.011
CYP2C19-substrate:	0.189
CYP2C9-inhibitor:	0.002
CYP2C9-substrate:	0.034
CYP2D6-inhibitor:	0.002
CYP2D6-substrate:	0.078
CYP3A4-inhibitor:	0.022
CYP3A4-substrate:	0.108

ADMET: Excretion

Clearance (CL):	1.399
Half-life (T1/2):	0.878

ADMET: Toxicity

hERG Blockers:	0.021
Human Hepatotoxicity (H-HT):	0.186
Drug-inuced Liver Injury (DILI):	0.66
AMES Toxicity:	0.245
Rat Oral Acute Toxicity:	0.628
Maximum Recommended Daily Dose:	0.027
Skin Sensitization:	0.51
Carcinogencity:	0.95
Eye Corrosion:	0.004
Eye Irritation:	0.629
Respiratory Toxicity:	0.296

Download Data

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

Natural Product: NPC220167

Natural Product ID:	NPC220167
*Common Name:**	Bartioside
IUPAC Name:	(2S,3R,4S,5S,6R)-2-[[(1S,4aR,7aS)-7-(hydroxymethyl)-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-1-yl]oxy]-6-(hydroxymethyl)oxane-3,4,5-triol
Synonyms:
Standard InCHIKey:	FCHJZJFIDNMNBS-CLBXSRGTSA-N
Standard InCHI:	InChI=1S/C15H22O8/c16-5-8-2-1-7-3-4-21-14(10(7)8)23-15-13(20)12(19)11(18)9(6-17)22-15/h2-4,7,9-20H,1,5-6H2/t7-,9-,10+,11-,12+,13-,14+,15+/m1/s1
SMILES:	C1C=C(CO)[C@@H]2[C@H]1C=CO[C@H]2O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3622807
PubChem CID:	10359257
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0002049] Terpene glycosides [CHEMONTID:0004081] Iridoid O-glycosides

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO15144	Combretum molle	Species	Combretaceae	Eukaryota	stem bark	n.a.	n.a.	PMID[19299148]
NPO33356	vitex mollis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26351040]
NPO20005	Penstemon barbatus	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26351040]
NPO33113	castilleja tenuiflora	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26351040]
NPO33328	cresentia alata	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[26351040]
NPO20867	Parmelinopsis bonariensis	Species	Parmeliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4856	Trichothecium crotocinigenum	Species	n.a.	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27353	Tovomita brevistaminea	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20607	Boussingaultia baselloides	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO20400	Physcia caesia	Species	Physciaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15144	Combretum molle	Species	Combretaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20005	Penstemon barbatus	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20733	Neonauclea calycina	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	6

Activity Type	# Activity
Individual Protein	6

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT30	Individual Protein	Cyclooxygenase-1	Homo sapiens	Inhibition	=	52.7	%	PMID[486886]
NPT30	Individual Protein	Cyclooxygenase-1	Homo sapiens	Inhibition	=	49.9	%	PMID[486886]
NPT30	Individual Protein	Cyclooxygenase-1	Homo sapiens	Inhibition	=	47.5	%	PMID[486886]
NPT31	Individual Protein	Cyclooxygenase-2	Homo sapiens	Inhibition	<=	30.0	%	PMID[486886]

☑ 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 NPC220167 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	182
0.1-0.2	1644
0.2-0.3	5771
0.3-0.4	15179
0.4-0.5	12610
0.5-0.6	6261
0.6-0.7	901
0.7-0.8	127
0.8-0.85	14
0.85-0.9	3
0.9-0.95	3
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC136699
0.907	High Similarity	NPC280390
0.8556	High Similarity	NPC241911
0.828	Intermediate Similarity	NPC255677
0.828	Intermediate Similarity	NPC22149
0.828	Intermediate Similarity	NPC306344
0.8256	Intermediate Similarity	NPC470658
0.8191	Intermediate Similarity	NPC298255
0.8191	Intermediate Similarity	NPC28304
0.8161	Intermediate Similarity	NPC171484
0.8161	Intermediate Similarity	NPC149018
0.814	Intermediate Similarity	NPC259296
0.814	Intermediate Similarity	NPC98276
0.8105	Intermediate Similarity	NPC250545
0.809	Intermediate Similarity	NPC104129
0.809	Intermediate Similarity	NPC249408
0.8021	Intermediate Similarity	NPC118761
0.8021	Intermediate Similarity	NPC284929
0.8021	Intermediate Similarity	NPC267869
0.8021	Intermediate Similarity	NPC197541
0.8021	Intermediate Similarity	NPC234304
0.7938	Intermediate Similarity	NPC86095
0.7917	Intermediate Similarity	NPC13171
0.7917	Intermediate Similarity	NPC195510
0.7917	Intermediate Similarity	NPC310804
0.7917	Intermediate Similarity	NPC261117
0.7917	Intermediate Similarity	NPC222062
0.7901	Intermediate Similarity	NPC132938
0.7865	Intermediate Similarity	NPC258501
0.7831	Intermediate Similarity	NPC229655
0.7826	Intermediate Similarity	NPC61201
0.7812	Intermediate Similarity	NPC20673
0.7802	Intermediate Similarity	NPC327253
0.7778	Intermediate Similarity	NPC148534
0.7717	Intermediate Similarity	NPC294643
0.7717	Intermediate Similarity	NPC473150
0.7717	Intermediate Similarity	NPC274274
0.7708	Intermediate Similarity	NPC244878
0.7692	Intermediate Similarity	NPC93190
0.7692	Intermediate Similarity	NPC22918
0.7692	Intermediate Similarity	NPC50464
0.7634	Intermediate Similarity	NPC320552
0.7604	Intermediate Similarity	NPC151093
0.7527	Intermediate Similarity	NPC276298
0.75	Intermediate Similarity	NPC20072
0.7474	Intermediate Similarity	NPC170204
0.7471	Intermediate Similarity	NPC100697
0.7449	Intermediate Similarity	NPC4637
0.7449	Intermediate Similarity	NPC219038
0.7449	Intermediate Similarity	NPC98859
0.7426	Intermediate Similarity	NPC254538
0.7426	Intermediate Similarity	NPC474285
0.7419	Intermediate Similarity	NPC303451
0.7419	Intermediate Similarity	NPC307699
0.7419	Intermediate Similarity	NPC117596
0.7419	Intermediate Similarity	NPC6414
0.7391	Intermediate Similarity	NPC137368
0.7391	Intermediate Similarity	NPC248312
0.7381	Intermediate Similarity	NPC472174
0.7374	Intermediate Similarity	NPC471599
0.7347	Intermediate Similarity	NPC469942
0.7342	Intermediate Similarity	NPC294813
0.7342	Intermediate Similarity	NPC13143
0.734	Intermediate Similarity	NPC472124
0.734	Intermediate Similarity	NPC472125
0.734	Intermediate Similarity	NPC472126
0.7333	Intermediate Similarity	NPC266718
0.7312	Intermediate Similarity	NPC299527
0.7292	Intermediate Similarity	NPC101051
0.7273	Intermediate Similarity	NPC470434
0.7228	Intermediate Similarity	NPC75608
0.7216	Intermediate Similarity	NPC161293
0.7172	Intermediate Similarity	NPC473146
0.7158	Intermediate Similarity	NPC302584
0.7158	Intermediate Similarity	NPC472199
0.7158	Intermediate Similarity	NPC9447
0.7158	Intermediate Similarity	NPC472197
0.7157	Intermediate Similarity	NPC472899
0.7157	Intermediate Similarity	NPC472898
0.7157	Intermediate Similarity	NPC472900
0.7143	Intermediate Similarity	NPC240372
0.7143	Intermediate Similarity	NPC475035
0.7143	Intermediate Similarity	NPC474194
0.7143	Intermediate Similarity	NPC470683
0.7143	Intermediate Similarity	NPC470684
0.7129	Intermediate Similarity	NPC473198
0.7128	Intermediate Similarity	NPC477748
0.7113	Intermediate Similarity	NPC469543
0.7113	Intermediate Similarity	NPC291709
0.7113	Intermediate Similarity	NPC241407
0.71	Intermediate Similarity	NPC285231
0.71	Intermediate Similarity	NPC21568
0.7097	Intermediate Similarity	NPC475037
0.7097	Intermediate Similarity	NPC125142
0.7097	Intermediate Similarity	NPC142583
0.7087	Intermediate Similarity	NPC33053
0.7083	Intermediate Similarity	NPC472195
0.7083	Intermediate Similarity	NPC472196
0.7083	Intermediate Similarity	NPC238090
0.7079	Intermediate Similarity	NPC163362
0.7079	Intermediate Similarity	NPC127295
0.7073	Intermediate Similarity	NPC59442
0.7071	Intermediate Similarity	NPC158088
0.7065	Intermediate Similarity	NPC477746
0.7065	Intermediate Similarity	NPC73166
0.7065	Intermediate Similarity	NPC477747
0.7065	Intermediate Similarity	NPC470124
0.7059	Intermediate Similarity	NPC93352
0.7053	Intermediate Similarity	NPC202886
0.7041	Intermediate Similarity	NPC90583
0.7041	Intermediate Similarity	NPC207617
0.7037	Intermediate Similarity	NPC147292
0.703	Intermediate Similarity	NPC272015
0.7019	Intermediate Similarity	NPC472897
0.7019	Intermediate Similarity	NPC472896
0.7011	Intermediate Similarity	NPC326661
0.701	Intermediate Similarity	NPC2003
0.701	Intermediate Similarity	NPC25701
0.701	Intermediate Similarity	NPC256368
0.701	Intermediate Similarity	NPC63897
0.701	Intermediate Similarity	NPC472198
0.701	Intermediate Similarity	NPC159698
0.7	Intermediate Similarity	NPC280367
0.7	Intermediate Similarity	NPC64348
0.7	Intermediate Similarity	NPC219656
0.6989	Remote Similarity	NPC470836
0.6979	Remote Similarity	NPC477749
0.6977	Remote Similarity	NPC472173
0.697	Remote Similarity	NPC153559
0.697	Remote Similarity	NPC472290
0.697	Remote Similarity	NPC473890
0.697	Remote Similarity	NPC243728
0.6962	Remote Similarity	NPC155457
0.6961	Remote Similarity	NPC197736
0.6947	Remote Similarity	NPC309310
0.6931	Remote Similarity	NPC267510
0.6931	Remote Similarity	NPC287539
0.6931	Remote Similarity	NPC3488
0.6931	Remote Similarity	NPC198992
0.6923	Remote Similarity	NPC231340
0.6923	Remote Similarity	NPC477390
0.6923	Remote Similarity	NPC477385
0.6907	Remote Similarity	NPC91654
0.6907	Remote Similarity	NPC474792
0.6907	Remote Similarity	NPC67398
0.69	Remote Similarity	NPC198422
0.69	Remote Similarity	NPC81483
0.69	Remote Similarity	NPC124181
0.69	Remote Similarity	NPC473307
0.69	Remote Similarity	NPC307517
0.69	Remote Similarity	NPC61630
0.69	Remote Similarity	NPC169468
0.69	Remote Similarity	NPC40182
0.69	Remote Similarity	NPC90819
0.6887	Remote Similarity	NPC141433
0.6882	Remote Similarity	NPC475034
0.6875	Remote Similarity	NPC231710
0.6875	Remote Similarity	NPC470573
0.6875	Remote Similarity	NPC65665
0.6875	Remote Similarity	NPC120021
0.6875	Remote Similarity	NPC159876
0.6875	Remote Similarity	NPC216826
0.6875	Remote Similarity	NPC233500
0.6875	Remote Similarity	NPC270908
0.6869	Remote Similarity	NPC54731
0.6869	Remote Similarity	NPC306041
0.6869	Remote Similarity	NPC256230
0.6863	Remote Similarity	NPC154452
0.6863	Remote Similarity	NPC304163
0.6863	Remote Similarity	NPC201191
0.6863	Remote Similarity	NPC136816
0.686	Remote Similarity	NPC55652
0.6857	Remote Similarity	NPC235824
0.6852	Remote Similarity	NPC307642
0.6848	Remote Similarity	NPC188717
0.6848	Remote Similarity	NPC211455
0.6848	Remote Similarity	NPC473315
0.6848	Remote Similarity	NPC142111
0.6842	Remote Similarity	NPC475991
0.6837	Remote Similarity	NPC477927
0.6837	Remote Similarity	NPC72817
0.6837	Remote Similarity	NPC315059
0.6832	Remote Similarity	NPC473200
0.6832	Remote Similarity	NPC7341
0.6832	Remote Similarity	NPC282669
0.6827	Remote Similarity	NPC127235
0.6824	Remote Similarity	NPC474078
0.6814	Remote Similarity	NPC196130
0.6813	Remote Similarity	NPC15978
0.6809	Remote Similarity	NPC472379
0.6809	Remote Similarity	NPC278283
0.6804	Remote Similarity	NPC235051
0.6796	Remote Similarity	NPC475928
0.6792	Remote Similarity	NPC472901
0.6778	Remote Similarity	NPC179933
0.6774	Remote Similarity	NPC116613
0.6774	Remote Similarity	NPC473308
0.6774	Remote Similarity	NPC32676
0.6771	Remote Similarity	NPC478110
0.6771	Remote Similarity	NPC473058

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 NPC220167 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	166
0.1-0.2	1945
0.2-0.3	4156
0.3-0.4	2169
0.4-0.5	551
0.5-0.6	142
0.6-0.7	21
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.6579	Remote Similarity	NPD7503	Approved
0.6458	Remote Similarity	NPD4249	Approved
0.6408	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6392	Remote Similarity	NPD4250	Approved
0.6392	Remote Similarity	NPD7524	Approved
0.6392	Remote Similarity	NPD4251	Approved
0.6389	Remote Similarity	NPD6686	Approved
0.6364	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6344	Remote Similarity	NPD7332	Phase 2
0.6293	Remote Similarity	NPD8513	Phase 3
0.625	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.62	Remote Similarity	NPD6698	Approved
0.62	Remote Similarity	NPD8522	Clinical (unspecified phase)
0.62	Remote Similarity	NPD46	Approved
0.6174	Remote Similarity	NPD7328	Approved
0.6174	Remote Similarity	NPD7327	Approved
0.617	Remote Similarity	NPD7514	Phase 3
0.6154	Remote Similarity	NPD8517	Approved
0.6154	Remote Similarity	NPD8516	Approved
0.6154	Remote Similarity	NPD8515	Approved
0.6154	Remote Similarity	NPD8033	Approved
0.6147	Remote Similarity	NPD6412	Phase 2
0.6146	Remote Similarity	NPD7154	Phase 3
0.6146	Remote Similarity	NPD6695	Phase 3
0.6146	Remote Similarity	NPD6110	Phase 1
0.6139	Remote Similarity	NPD7983	Approved
0.6139	Remote Similarity	NPD7637	Suspended
0.6129	Remote Similarity	NPD7145	Approved
0.6121	Remote Similarity	NPD7516	Approved
0.6105	Remote Similarity	NPD6902	Approved
0.6082	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6076	Remote Similarity	NPD895	Approved
0.6076	Remote Similarity	NPD890	Clinical (unspecified phase)
0.6076	Remote Similarity	NPD894	Approved
0.6076	Remote Similarity	NPD893	Approved
0.6076	Remote Similarity	NPD889	Approved
0.6076	Remote Similarity	NPD891	Phase 3
0.6076	Remote Similarity	NPD887	Approved
0.6076	Remote Similarity	NPD892	Phase 3
0.6076	Remote Similarity	NPD888	Phase 3
0.6068	Remote Similarity	NPD8377	Approved
0.6068	Remote Similarity	NPD8294	Approved
0.604	Remote Similarity	NPD7838	Discovery
0.6026	Remote Similarity	NPD904	Phase 3
0.6026	Remote Similarity	NPD905	Approved
0.6022	Remote Similarity	NPD6925	Approved
0.6022	Remote Similarity	NPD5776	Phase 2
0.6017	Remote Similarity	NPD8296	Approved
0.6017	Remote Similarity	NPD8335	Approved
0.6017	Remote Similarity	NPD8379	Approved
0.6017	Remote Similarity	NPD8380	Approved
0.6017	Remote Similarity	NPD8378	Approved
0.6	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.5957	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.5938	Remote Similarity	NPD6898	Phase 1
0.59	Remote Similarity	NPD7750	Discontinued
0.5895	Remote Similarity	NPD6929	Approved
0.5882	Remote Similarity	NPD368	Approved
0.5872	Remote Similarity	NPD1407	Approved
0.5851	Remote Similarity	NPD6932	Approved
0.5833	Remote Similarity	NPD6931	Approved
0.5833	Remote Similarity	NPD5344	Discontinued
0.5833	Remote Similarity	NPD6930	Phase 2
0.582	Remote Similarity	NPD7507	Approved
0.5816	Remote Similarity	NPD5362	Discontinued
0.5789	Remote Similarity	NPD4271	Approved
0.5789	Remote Similarity	NPD4268	Approved
0.5766	Remote Similarity	NPD6640	Phase 3
0.5755	Remote Similarity	NPD7839	Suspended
0.575	Remote Similarity	NPD2269	Approved
0.5738	Remote Similarity	NPD1091	Approved
0.5728	Remote Similarity	NPD7136	Phase 2
0.5714	Remote Similarity	NPD5282	Discontinued
0.568	Remote Similarity	NPD7319	Approved
0.5673	Remote Similarity	NPD7087	Discontinued
0.567	Remote Similarity	NPD4822	Approved
0.567	Remote Similarity	NPD4820	Approved
0.567	Remote Similarity	NPD4819	Approved
0.567	Remote Similarity	NPD4821	Approved
0.5645	Remote Similarity	NPD8074	Phase 3
0.5619	Remote Similarity	NPD5778	Approved
0.5619	Remote Similarity	NPD5779	Approved
0.5612	Remote Similarity	NPD4790	Discontinued
0.561	Remote Similarity	NPD8342	Approved
0.561	Remote Similarity	NPD8299	Approved
0.561	Remote Similarity	NPD8340	Approved
0.561	Remote Similarity	NPD8341	Approved
0.5603	Remote Similarity	NPD6429	Approved
0.5603	Remote Similarity	NPD6430	Approved
0.5603	Remote Similarity	NPD6053	Discontinued

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data