NPASS Compound

Structure

NPC473285 OpenBabel07101718182D 34 36 0 0 1 0 0 0 0 0999 V2000 1.7321 -0.0000 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 -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 -1.0000 0.0000 C 0 0 0 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 -0.0000 -3.0000 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 -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 -0.8660 -2.5000 0.0000 C 0 0 2 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 0.8660 1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 2.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 C 0 0 2 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 2 0 0 0 0 0 0 0 0 0 -2.5981 -2.5000 0.0000 C 0 0 2 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 -0.0000 -4.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -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 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 3.0000 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 -3.4641 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -3.0000 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 -1.7321 -3.0000 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 -1.7321 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 4 2 0 0 0 0 2 9 1 0 0 0 0 3 5 2 0 0 0 0 3 9 1 0 0 0 0 4 10 1 0 0 0 0 5 13 1 0 0 0 0 6 9 2 0 0 0 0 6 11 1 0 0 0 0 7 22 1 0 0 0 0 8 1 1 1 0 0 0 8 14 1 0 0 0 0 8 31 1 0 0 0 0 10 11 2 0 0 0 0 10 23 1 0 0 0 0 11 24 1 0 0 0 0 12 7 1 1 0 0 0 12 18 1 0 0 0 0 12 32 1 0 0 0 0 13 25 2 0 0 0 0 13 33 1 0 0 0 0 14 15 1 0 0 0 0 14 26 1 6 0 0 0 15 16 1 0 0 0 0 15 27 1 1 0 0 0 16 21 1 0 0 0 0 16 28 1 1 0 0 0 17 19 1 0 0 0 0 17 20 1 0 0 0 0 17 29 1 6 0 0 0 18 19 1 0 0 0 0 18 33 1 6 0 0 0 19 34 1 1 0 0 0 20 30 1 1 0 0 0 20 32 1 0 0 0 0 21 31 1 0 0 0 0 21 34 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	488.15
Volume:	447.193
LogP:	-0.642
LogD:	-0.574
LogS:	-1.368
# Rotatable Bonds:	7
TPSA:	215.83
# H-Bond Aceptor:	13
# H-Bond Donor:	8
# Rings:	3
# Heavy Atoms:	13

MedChem Properties

QED Drug-Likeness Score:	0.116
Synthetic Accessibility Score:	4.535
Fsp3:	0.571
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.531
MDCK Permeability:	7.401072070933878e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.987
Human Intestinal Absorption (HIA):	0.919
20% Bioavailability (F20%):	0.85
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.175
Plasma Protein Binding (PPB):	72.0441665649414%
Volume Distribution (VD):	0.41
Pgp-substrate:	30.568445205688477%

ADMET: Metabolism

CYP1A2-inhibitor:	0.073
CYP1A2-substrate:	0.014
CYP2C19-inhibitor:	0.04
CYP2C19-substrate:	0.059
CYP2C9-inhibitor:	0.008
CYP2C9-substrate:	0.099
CYP2D6-inhibitor:	0.006
CYP2D6-substrate:	0.129
CYP3A4-inhibitor:	0.028
CYP3A4-substrate:	0.023

ADMET: Excretion

Clearance (CL):	1.311
Half-life (T1/2):	0.809

ADMET: Toxicity

hERG Blockers:	0.086
Human Hepatotoxicity (H-HT):	0.285
Drug-inuced Liver Injury (DILI):	0.3
AMES Toxicity:	0.621
Rat Oral Acute Toxicity:	0.134
Maximum Recommended Daily Dose:	0.002
Skin Sensitization:	0.895
Carcinogencity:	0.036
Eye Corrosion:	0.003
Eye Irritation:	0.017
Respiratory Toxicity:	0.028

Download Data

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

Natural Product: NPC473285

Natural Product ID:	NPC473285
*Common Name:**	Cistanoside F
IUPAC Name:	[(2R,3R,4R,5R,6R)-5,6-dihydroxy-2-(hydroxymethyl)-4-[(2R,3S,4S,5S,6R)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-3-yl] (E)-3-(3,4-dihydroxyphenyl)prop-2-enoate
Synonyms:	Cistanoside F
Standard InCHIKey:	IDVRYIVYDAOHSS-CRADLMAESA-N
Standard InCHI:	InChI=1S/C21H28O13/c1-8-14(26)15(27)16(28)21(31-8)34-19-17(29)20(30)32-12(7-22)18(19)33-13(25)5-3-9-2-4-10(23)11(24)6-9/h2-6,8,12,14-24,26-30H,7H2,1H3/b5-3+/t8-,12-,14-,15+,16+,17-,18-,19-,20-,21-/m1/s1
SMILES:	CC1C(C(C(C(O1)OC2C(C(OC(C2OC(=O)C=CC3=CC(=C(C=C3)O)O)CO)O)O)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL393549
PubChem CID:	44429870
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000476] Cinnamic acids and derivatives [CHEMONTID:0001391] Hydroxycinnamic acids and derivatives [CHEMONTID:0000059] Coumaric acids and derivatives

*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
NPO6536	Marrubium velutinum	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17287127]
NPO6964	Cistanche tubulosa	Species	Orobanchaceae	Eukaryota	fresh stems	n.a.	n.a.	PMID[20159656]
NPO6964	Cistanche tubulosa	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO6536	Marrubium velutinum	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6964	Cistanche tubulosa	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6964	Cistanche tubulosa	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO6536	Marrubium velutinum	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6964	Cistanche tubulosa	Species	Orobanchaceae	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	5

Activity Type	# Activity
Cell Line	4
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT43	Individual Protein	Tyrosinase	Agaricus bisporus	Inhibition	=	10.92	%	PMID[540271]
NPT993	Cell Line	Hepatocyte	Mus musculus	Inhibition	=	2.0	%	PMID[540272]
NPT993	Cell Line	Hepatocyte	Mus musculus	Inhibition	=	4.0	%	PMID[540272]
NPT993	Cell Line	Hepatocyte	Mus musculus	Inhibition	=	7.7	%	PMID[540272]
NPT993	Cell Line	Hepatocyte	Mus musculus	Inhibition	=	21.2	%	PMID[540272]

☑ 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 NPC473285 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	284
0.1-0.2	1325
0.2-0.3	3368
0.3-0.4	8163
0.4-0.5	9929
0.5-0.6	7380
0.6-0.7	8727
0.7-0.8	2949
0.8-0.85	372
0.85-0.9	122
0.9-0.95	70
0.95-1	8

Similarity Score	Similarity Level	Natural Product ID
0.976	High Similarity	NPC477294
0.976	High Similarity	NPC229784
0.976	High Similarity	NPC477293
0.968	High Similarity	NPC232880
0.9615	High Similarity	NPC476376
0.9609	High Similarity	NPC254398
0.9606	High Similarity	NPC219677
0.96	High Similarity	NPC476873
0.9542	High Similarity	NPC472350
0.9542	High Similarity	NPC89105
0.9542	High Similarity	NPC68092
0.9542	High Similarity	NPC476383
0.9542	High Similarity	NPC64141
0.9542	High Similarity	NPC81515
0.9542	High Similarity	NPC197316
0.9535	High Similarity	NPC471883
0.9535	High Similarity	NPC886
0.9535	High Similarity	NPC34293
0.9535	High Similarity	NPC287597
0.9531	High Similarity	NPC473924
0.9466	High Similarity	NPC78363
0.9466	High Similarity	NPC260425
0.9462	High Similarity	NPC476870
0.9398	High Similarity	NPC476385
0.9398	High Similarity	NPC476377
0.9398	High Similarity	NPC47471
0.9398	High Similarity	NPC134405
0.9394	High Similarity	NPC205195
0.9389	High Similarity	NPC157554
0.9365	High Similarity	NPC471157
0.9328	High Similarity	NPC222433
0.9328	High Similarity	NPC265648
0.9323	High Similarity	NPC475530
0.9323	High Similarity	NPC202700
0.9323	High Similarity	NPC473799
0.9291	High Similarity	NPC106677
0.9286	High Similarity	NPC126991
0.9286	High Similarity	NPC83218
0.9259	High Similarity	NPC476378
0.9259	High Similarity	NPC476380
0.9259	High Similarity	NPC205864
0.9259	High Similarity	NPC175214
0.9259	High Similarity	NPC112
0.9259	High Similarity	NPC119537
0.9259	High Similarity	NPC298257
0.9259	High Similarity	NPC76406
0.9259	High Similarity	NPC476384
0.9259	High Similarity	NPC476375
0.9259	High Similarity	NPC96795
0.9259	High Similarity	NPC247032
0.9259	High Similarity	NPC264632
0.9259	High Similarity	NPC476381
0.9259	High Similarity	NPC269141
0.9259	High Similarity	NPC476397
0.9248	High Similarity	NPC226005
0.9248	High Similarity	NPC321184
0.9248	High Similarity	NPC328273
0.9248	High Similarity	NPC100389
0.9248	High Similarity	NPC171134
0.9248	High Similarity	NPC321638
0.9248	High Similarity	NPC220942
0.9242	High Similarity	NPC470572
0.92	High Similarity	NPC52097
0.9191	High Similarity	NPC196063
0.9191	High Similarity	NPC64195
0.9191	High Similarity	NPC296954
0.9191	High Similarity	NPC300894
0.9191	High Similarity	NPC141455
0.9185	High Similarity	NPC157816
0.9185	High Similarity	NPC140502
0.9124	High Similarity	NPC476382
0.9124	High Similarity	NPC34927
0.9124	High Similarity	NPC34587
0.9124	High Similarity	NPC252292
0.9124	High Similarity	NPC100998
0.912	High Similarity	NPC11724
0.9118	High Similarity	NPC105005
0.9118	High Similarity	NPC478239
0.9111	High Similarity	NPC186406
0.9098	High Similarity	NPC37468
0.9098	High Similarity	NPC186418
0.9062	High Similarity	NPC252114
0.9058	High Similarity	NPC476865
0.9058	High Similarity	NPC229505
0.9051	High Similarity	NPC110063
0.9051	High Similarity	NPC476867
0.9044	High Similarity	NPC296643
0.904	High Similarity	NPC476872
0.9008	High Similarity	NPC46137
0.9008	High Similarity	NPC235294
0.9008	High Similarity	NPC246869
0.9008	High Similarity	NPC138777
0.9008	High Similarity	NPC225384
0.8993	High Similarity	NPC232992
0.8992	High Similarity	NPC45224
0.8992	High Similarity	NPC288416
0.8992	High Similarity	NPC471882
0.8992	High Similarity	NPC173150
0.8992	High Similarity	NPC471881
0.8992	High Similarity	NPC156692
0.8992	High Similarity	NPC35288
0.8986	High Similarity	NPC476869
0.8986	High Similarity	NPC262182
0.8986	High Similarity	NPC476864
0.8986	High Similarity	NPC287615
0.8986	High Similarity	NPC476866
0.8986	High Similarity	NPC216819
0.8986	High Similarity	NPC476868
0.8986	High Similarity	NPC83743
0.8978	High Similarity	NPC40305
0.8923	High Similarity	NPC225307
0.8921	High Similarity	NPC199928
0.8913	High Similarity	NPC292443
0.8913	High Similarity	NPC297342
0.8913	High Similarity	NPC232228
0.8865	High Similarity	NPC259347
0.8865	High Similarity	NPC94871
0.8865	High Similarity	NPC476398
0.8865	High Similarity	NPC306890
0.8865	High Similarity	NPC470933
0.8865	High Similarity	NPC471062
0.8865	High Similarity	NPC473427
0.8865	High Similarity	NPC476386
0.8855	High Similarity	NPC253595
0.8855	High Similarity	NPC307110
0.8819	High Similarity	NPC266045
0.8806	High Similarity	NPC35731
0.8803	High Similarity	NPC257970
0.8803	High Similarity	NPC188393
0.8803	High Similarity	NPC470927
0.8803	High Similarity	NPC69367
0.8803	High Similarity	NPC470934
0.8797	High Similarity	NPC254275
0.8794	High Similarity	NPC28651
0.8794	High Similarity	NPC210611
0.8794	High Similarity	NPC23677
0.8794	High Similarity	NPC80732
0.8794	High Similarity	NPC201148
0.8794	High Similarity	NPC478237
0.8794	High Similarity	NPC215095
0.8794	High Similarity	NPC261122
0.8794	High Similarity	NPC199311
0.8794	High Similarity	NPC192763
0.8794	High Similarity	NPC3460
0.8794	High Similarity	NPC300262
0.8769	High Similarity	NPC61181
0.8741	High Similarity	NPC123988
0.8741	High Similarity	NPC55040
0.8741	High Similarity	NPC263829
0.8732	High Similarity	NPC283839
0.8732	High Similarity	NPC90896
0.8732	High Similarity	NPC106138
0.8732	High Similarity	NPC478242
0.8723	High Similarity	NPC18789
0.8722	High Similarity	NPC65942
0.8722	High Similarity	NPC478255
0.8722	High Similarity	NPC281798
0.8722	High Similarity	NPC254819
0.8722	High Similarity	NPC248307
0.8712	High Similarity	NPC184092
0.8702	High Similarity	NPC103533
0.8702	High Similarity	NPC231607
0.8702	High Similarity	NPC108659
0.8702	High Similarity	NPC79715
0.8702	High Similarity	NPC264900
0.8692	High Similarity	NPC90318
0.8682	High Similarity	NPC474275
0.8682	High Similarity	NPC224208
0.8681	High Similarity	NPC106818
0.8676	High Similarity	NPC154485
0.8676	High Similarity	NPC471872
0.8671	High Similarity	NPC476871
0.8667	High Similarity	NPC135127
0.8657	High Similarity	NPC252833
0.8652	High Similarity	NPC473867
0.864	High Similarity	NPC281277
0.8636	High Similarity	NPC148982
0.8626	High Similarity	NPC94179
0.8621	High Similarity	NPC87403
0.8613	High Similarity	NPC126206
0.8613	High Similarity	NPC310252
0.8613	High Similarity	NPC100558
0.8613	High Similarity	NPC302583
0.8613	High Similarity	NPC304152
0.8613	High Similarity	NPC84789
0.8611	High Similarity	NPC7145
0.8611	High Similarity	NPC85192
0.8611	High Similarity	NPC125823
0.8611	High Similarity	NPC213197
0.8611	High Similarity	NPC478249
0.8611	High Similarity	NPC143480
0.8611	High Similarity	NPC269914
0.8603	High Similarity	NPC185778
0.8593	High Similarity	NPC6836
0.8593	High Similarity	NPC132895
0.8593	High Similarity	NPC28637
0.8592	High Similarity	NPC41844
0.8571	High Similarity	NPC248355
0.8571	High Similarity	NPC295970
0.856	High Similarity	NPC233669

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 NPC473285 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	232
0.1-0.2	770
0.2-0.3	1684
0.3-0.4	3027
0.4-0.5	1901
0.5-0.6	1116
0.6-0.7	382
0.7-0.8	36
0.8-0.85	1
0.85-0.9	0
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9542	High Similarity	NPD7266	Discontinued
0.8472	Intermediate Similarity	NPD1653	Approved
0.8182	Intermediate Similarity	NPD6190	Approved
0.7676	Intermediate Similarity	NPD230	Phase 1
0.7654	Intermediate Similarity	NPD7685	Pre-registration
0.7643	Intermediate Similarity	NPD3027	Phase 3
0.7591	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7578	Intermediate Similarity	NPD7054	Approved
0.7574	Intermediate Similarity	NPD1091	Approved
0.7531	Intermediate Similarity	NPD7472	Approved
0.7531	Intermediate Similarity	NPD7074	Phase 3
0.7516	Intermediate Similarity	NPD7228	Approved
0.7485	Intermediate Similarity	NPD6797	Phase 2
0.7483	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD1613	Approved
0.7481	Intermediate Similarity	NPD1357	Approved
0.7467	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7439	Intermediate Similarity	NPD7251	Discontinued
0.7407	Intermediate Similarity	NPD3818	Discontinued
0.7405	Intermediate Similarity	NPD6234	Discontinued
0.7394	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7389	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7319	Intermediate Similarity	NPD3705	Approved
0.7308	Intermediate Similarity	NPD37	Approved
0.7289	Intermediate Similarity	NPD7808	Phase 3
0.7278	Intermediate Similarity	NPD4967	Phase 2
0.7278	Intermediate Similarity	NPD4965	Approved
0.7278	Intermediate Similarity	NPD4966	Approved
0.7267	Intermediate Similarity	NPD8166	Discontinued
0.7233	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7231	Intermediate Similarity	NPD1358	Approved
0.7203	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD6674	Discontinued
0.716	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7153	Intermediate Similarity	NPD9545	Approved
0.7152	Intermediate Similarity	NPD8455	Phase 2
0.7143	Intermediate Similarity	NPD228	Approved
0.7143	Intermediate Similarity	NPD969	Suspended
0.7133	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD6559	Discontinued
0.7121	Intermediate Similarity	NPD3021	Approved
0.7121	Intermediate Similarity	NPD3022	Approved
0.7097	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD4978	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD1934	Approved
0.7086	Intermediate Similarity	NPD1652	Phase 2
0.708	Intermediate Similarity	NPD5536	Phase 2
0.7073	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD6166	Phase 2
0.7073	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7066	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7044	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD4628	Phase 3
0.7024	Intermediate Similarity	NPD7240	Approved
0.7023	Intermediate Similarity	NPD3134	Approved
0.7021	Intermediate Similarity	NPD9269	Phase 2
0.7014	Intermediate Similarity	NPD9494	Approved
0.7006	Intermediate Similarity	NPD3455	Phase 2
0.6994	Remote Similarity	NPD7199	Phase 2
0.6954	Remote Similarity	NPD2029	Clinical (unspecified phase)
0.6946	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6941	Remote Similarity	NPD8313	Approved
0.6941	Remote Similarity	NPD8312	Approved
0.6929	Remote Similarity	NPD5125	Phase 3
0.6929	Remote Similarity	NPD5126	Approved
0.6894	Remote Similarity	NPD3817	Phase 2
0.6892	Remote Similarity	NPD4060	Phase 1
0.6879	Remote Similarity	NPD3496	Discontinued
0.6867	Remote Similarity	NPD7097	Phase 1
0.6855	Remote Similarity	NPD4380	Phase 2
0.6853	Remote Similarity	NPD2983	Phase 2
0.6853	Remote Similarity	NPD2982	Phase 2
0.6846	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6846	Remote Similarity	NPD4340	Discontinued
0.6846	Remote Similarity	NPD5124	Phase 1
0.6845	Remote Similarity	NPD5844	Phase 1
0.6839	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD5058	Phase 3
0.6835	Remote Similarity	NPD3687	Approved
0.6835	Remote Similarity	NPD3686	Approved
0.6832	Remote Similarity	NPD2977	Approved
0.6832	Remote Similarity	NPD2978	Approved
0.6832	Remote Similarity	NPD1465	Phase 2
0.6832	Remote Similarity	NPD2801	Approved
0.6831	Remote Similarity	NPD422	Phase 1
0.6824	Remote Similarity	NPD6233	Phase 2
0.681	Remote Similarity	NPD7075	Discontinued
0.6809	Remote Similarity	NPD9381	Approved
0.6809	Remote Similarity	NPD9384	Approved
0.6807	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.68	Remote Similarity	NPD6653	Approved
0.6788	Remote Similarity	NPD8127	Discontinued
0.6783	Remote Similarity	NPD2981	Phase 2
0.6781	Remote Similarity	NPD2861	Phase 2
0.6779	Remote Similarity	NPD826	Approved
0.6779	Remote Similarity	NPD3620	Phase 2
0.6779	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6779	Remote Similarity	NPD825	Approved
0.6776	Remote Similarity	NPD9570	Approved
0.6761	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6759	Remote Similarity	NPD3094	Phase 2
0.6757	Remote Similarity	NPD3764	Approved
0.6748	Remote Similarity	NPD3882	Suspended
0.6738	Remote Similarity	NPD9268	Approved
0.6736	Remote Similarity	NPD9622	Approved
0.6733	Remote Similarity	NPD447	Suspended
0.6733	Remote Similarity	NPD1933	Approved
0.6722	Remote Similarity	NPD7237	Clinical (unspecified phase)
0.6715	Remote Similarity	NPD7843	Approved
0.671	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6691	Remote Similarity	NPD7157	Approved
0.6691	Remote Similarity	NPD9280	Clinical (unspecified phase)
0.669	Remote Similarity	NPD4626	Approved
0.6689	Remote Similarity	NPD2492	Phase 1
0.6689	Remote Similarity	NPD7095	Approved
0.6688	Remote Similarity	NPD4357	Discontinued
0.6688	Remote Similarity	NPD1511	Approved
0.6687	Remote Similarity	NPD5402	Approved
0.6686	Remote Similarity	NPD6843	Phase 3
0.6686	Remote Similarity	NPD6842	Approved
0.6686	Remote Similarity	NPD6841	Approved
0.6667	Remote Similarity	NPD3062	Approved
0.6667	Remote Similarity	NPD7680	Approved
0.6667	Remote Similarity	NPD3059	Approved
0.6667	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5736	Approved
0.6667	Remote Similarity	NPD2935	Discontinued
0.6667	Remote Similarity	NPD3018	Phase 2
0.6667	Remote Similarity	NPD3061	Approved
0.6667	Remote Similarity	NPD2684	Approved
0.6667	Remote Similarity	NPD5283	Phase 1
0.6647	Remote Similarity	NPD6232	Discontinued
0.6646	Remote Similarity	NPD4160	Clinical (unspecified phase)
0.6646	Remote Similarity	NPD8389	Clinical (unspecified phase)
0.6645	Remote Similarity	NPD5698	Clinical (unspecified phase)
0.6645	Remote Similarity	NPD4538	Approved
0.6645	Remote Similarity	NPD4537	Clinical (unspecified phase)
0.6645	Remote Similarity	NPD4536	Approved
0.6644	Remote Similarity	NPD6798	Discontinued
0.6641	Remote Similarity	NPD1242	Phase 1
0.6626	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6623	Remote Similarity	NPD555	Phase 2
0.6623	Remote Similarity	NPD5763	Approved
0.6623	Remote Similarity	NPD5762	Approved
0.6622	Remote Similarity	NPD4908	Phase 1
0.662	Remote Similarity	NPD5691	Approved
0.6604	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.6604	Remote Similarity	NPD1512	Approved
0.6603	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6603	Remote Similarity	NPD4110	Phase 3
0.6603	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6599	Remote Similarity	NPD9620	Approved
0.6599	Remote Similarity	NPD9621	Approved
0.6599	Remote Similarity	NPD9619	Approved
0.6597	Remote Similarity	NPD3092	Approved
0.6593	Remote Similarity	NPD290	Approved
0.6588	Remote Similarity	NPD3751	Discontinued
0.6585	Remote Similarity	NPD5353	Approved
0.6581	Remote Similarity	NPD2424	Discontinued
0.6579	Remote Similarity	NPD5314	Approved
0.6573	Remote Similarity	NPD1778	Approved
0.6564	Remote Similarity	NPD6801	Discontinued
0.6562	Remote Similarity	NPD5403	Approved
0.6556	Remote Similarity	NPD4140	Approved
0.6556	Remote Similarity	NPD1558	Phase 1
0.6556	Remote Similarity	NPD943	Approved
0.6538	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6538	Remote Similarity	NPD3060	Approved
0.6538	Remote Similarity	NPD4237	Approved
0.6538	Remote Similarity	NPD4236	Phase 3
0.6533	Remote Similarity	NPD598	Approved
0.6533	Remote Similarity	NPD601	Approved
0.6533	Remote Similarity	NPD597	Approved
0.6533	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6533	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6532	Remote Similarity	NPD7038	Approved
0.6532	Remote Similarity	NPD7039	Approved
0.6529	Remote Similarity	NPD7473	Discontinued
0.6525	Remote Similarity	NPD9493	Approved
0.6525	Remote Similarity	NPD694	Clinical (unspecified phase)
0.6524	Remote Similarity	NPD7819	Suspended
0.6516	Remote Similarity	NPD1375	Discontinued
0.6514	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6513	Remote Similarity	NPD6355	Discontinued
0.6512	Remote Similarity	NPD2934	Approved
0.6512	Remote Similarity	NPD2933	Approved
0.6503	Remote Similarity	NPD6385	Approved
0.6503	Remote Similarity	NPD6386	Approved
0.6494	Remote Similarity	NPD7033	Discontinued
0.6494	Remote Similarity	NPD4108	Discontinued
0.6494	Remote Similarity	NPD5588	Approved
0.6494	Remote Similarity	NPD7549	Discontinued
0.6494	Remote Similarity	NPD5960	Phase 3
0.649	Remote Similarity	NPD4062	Phase 3
0.649	Remote Similarity	NPD1136	Approved
0.649	Remote Similarity	NPD1132	Approved
0.649	Remote Similarity	NPD259	Phase 1
0.649	Remote Similarity	NPD6663	Approved
0.649	Remote Similarity	NPD1130	Approved
0.6486	Remote Similarity	NPD258	Approved

Bioactivity similarity: Similar Natural Products in NPASS

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

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

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data