NPASS Compound

Structure

NPC254398 OpenBabel07101719522D 35 37 0 0 1 0 0 0 0 0999 V2000 1.7226 1.1810 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5909 -2.0032 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1932 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6728 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0592 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5388 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0592 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9511 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0029 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4049 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1932 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9253 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9253 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1369 -2.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.4049 -4.0000 0.0000 C 0 0 0 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 -2.4049 -2.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.4049 -1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.2709 -2.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.2709 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.9511 -0.3090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.5388 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.0029 -3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.7913 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.7913 -4.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4049 -5.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5388 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5388 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4049 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8090 1.5878 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2601 -1.2601 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.2709 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.1369 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.2709 -3.5000 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 1 30 1 0 0 0 0 2 31 1 0 0 0 0 3 5 2 0 0 0 0 3 11 1 0 0 0 0 4 6 2 0 0 0 0 4 11 1 0 0 0 0 5 12 1 0 0 0 0 6 15 1 0 0 0 0 7 11 2 0 0 0 0 7 13 1 0 0 0 0 8 16 1 0 0 0 0 8 22 1 0 0 0 0 9 23 1 0 0 0 0 10 22 1 0 0 0 0 10 32 1 0 0 0 0 12 13 2 0 0 0 0 12 24 1 0 0 0 0 13 25 1 0 0 0 0 14 9 1 1 0 0 0 14 19 1 0 0 0 0 14 33 1 0 0 0 0 15 26 2 0 0 0 0 15 34 1 0 0 0 0 16 30 1 1 0 0 0 16 35 1 0 0 0 0 17 18 1 0 0 0 0 17 19 1 0 0 0 0 17 27 1 1 0 0 0 18 20 1 0 0 0 0 18 28 1 6 0 0 0 19 34 1 6 0 0 0 20 32 1 1 0 0 0 20 33 1 0 0 0 0 21 22 1 1 0 0 0 21 31 1 0 0 0 0 21 35 1 0 0 0 0 22 29 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	502.17
Volume:	464.489
LogP:	0.58
LogD:	-0.088
LogS:	-1.863
# Rotatable Bonds:	10
TPSA:	193.83
# H-Bond Aceptor:	13
# H-Bond Donor:	6
# Rings:	3
# Heavy Atoms:	13

MedChem Properties

QED Drug-Likeness Score:	0.131
Synthetic Accessibility Score:	4.821
Fsp3:	0.591
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.333
MDCK Permeability:	6.760583346476778e-05
Pgp-inhibitor:	0.003
Pgp-substrate:	0.998
Human Intestinal Absorption (HIA):	0.876
20% Bioavailability (F20%):	0.891
30% Bioavailability (F30%):	0.995

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.198
Plasma Protein Binding (PPB):	66.15966033935547%
Volume Distribution (VD):	0.331
Pgp-substrate:	37.76171875%

ADMET: Metabolism

CYP1A2-inhibitor:	0.012
CYP1A2-substrate:	0.355
CYP2C19-inhibitor:	0.016
CYP2C19-substrate:	0.063
CYP2C9-inhibitor:	0.009
CYP2C9-substrate:	0.059
CYP2D6-inhibitor:	0.003
CYP2D6-substrate:	0.117
CYP3A4-inhibitor:	0.026
CYP3A4-substrate:	0.064

ADMET: Excretion

Clearance (CL):	1.169
Half-life (T1/2):	0.842

ADMET: Toxicity

hERG Blockers:	0.049
Human Hepatotoxicity (H-HT):	0.219
Drug-inuced Liver Injury (DILI):	0.27
AMES Toxicity:	0.902
Rat Oral Acute Toxicity:	0.071
Maximum Recommended Daily Dose:	0.02
Skin Sensitization:	0.94
Carcinogencity:	0.132
Eye Corrosion:	0.003
Eye Irritation:	0.018
Respiratory Toxicity:	0.103

Download Data

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

Natural Product: NPC254398

Natural Product ID:	NPC254398
*Common Name:**	Cibotiumbaroside B
IUPAC Name:	[(2R,3S,4R,5R,6R)-4,5-dihydroxy-6-[[(2R,3S,5S)-3-hydroxy-2,5-dimethoxyoxolan-3-yl]methoxy]-2-(hydroxymethyl)oxan-3-yl] (E)-3-(3,4-dihydroxyphenyl)prop-2-enoate
Synonyms:	Cibotiumbaroside B
Standard InCHIKey:	FETGVTKHZTUDCC-ZIYLAOJSSA-N
Standard InCHI:	InChI=1S/C22H30O13/c1-30-16-8-22(29,21(31-2)35-16)10-32-20-18(28)17(27)19(14(9-23)33-20)34-15(26)6-4-11-3-5-12(24)13(25)7-11/h3-7,14,16-21,23-25,27-29H,8-10H2,1-2H3/b6-4+/t14-,16+,17-,18-,19-,20-,21-,22+/m1/s1
SMILES:	OC[C@H]1O[C@@H](OC[C@@]2(O)C[C@H](O[C@H]2OC)OC)[C@@H]([C@H]([C@@H]1OC(=O)/C=C/c1ccc(c(c1)O)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1078424
PubChem CID:	44481790
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
NPO24811	Cibotium barometz	Species	Cibotiaceae	Eukaryota	rhizomes	n.a.	n.a.	PMID[19739599]
NPO24811	Cibotium barometz	Species	Cibotiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO24811	Cibotium barometz	Species	Cibotiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24811	Cibotium barometz	Species	Cibotiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO24811	Cibotium barometz	Species	Cibotiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO24811	Cibotium barometz	Species	Cibotiaceae	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	1

Activity Type	# Activity
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified		Inhibition	=	73.0	%	PMID[467970]

☑ 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 NPC254398 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	266
0.1-0.2	1179
0.2-0.3	3035
0.3-0.4	7651
0.4-0.5	10346
0.5-0.6	8420
0.6-0.7	8998
0.7-0.8	2314
0.8-0.85	308
0.85-0.9	128
0.9-0.95	48
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9921	High Similarity	NPC473924
0.9841	High Similarity	NPC219677
0.9766	High Similarity	NPC471883
0.9683	High Similarity	NPC477293
0.9683	High Similarity	NPC477294
0.9683	High Similarity	NPC229784
0.9609	High Similarity	NPC473285
0.9603	High Similarity	NPC232880
0.9524	High Similarity	NPC476873
0.947	High Similarity	NPC321184
0.947	High Similarity	NPC171134
0.947	High Similarity	NPC328273
0.947	High Similarity	NPC226005
0.947	High Similarity	NPC321638
0.947	High Similarity	NPC220942
0.9466	High Similarity	NPC470572
0.9318	High Similarity	NPC157554
0.9313	High Similarity	NPC886
0.9313	High Similarity	NPC34293
0.9313	High Similarity	NPC287597
0.9265	High Similarity	NPC300894
0.9265	High Similarity	NPC141455
0.9265	High Similarity	NPC110063
0.9265	High Similarity	NPC196063
0.9265	High Similarity	NPC296954
0.9248	High Similarity	NPC476376
0.9242	High Similarity	NPC476870
0.9219	High Similarity	NPC471882
0.9219	High Similarity	NPC156692
0.9219	High Similarity	NPC173150
0.9219	High Similarity	NPC35288
0.9219	High Similarity	NPC471881
0.9219	High Similarity	NPC45224
0.9191	High Similarity	NPC105005
0.9191	High Similarity	NPC40305
0.9179	High Similarity	NPC476383
0.9179	High Similarity	NPC68092
0.9179	High Similarity	NPC197316
0.9179	High Similarity	NPC64141
0.9179	High Similarity	NPC100389
0.9179	High Similarity	NPC472350
0.9179	High Similarity	NPC89105
0.9179	High Similarity	NPC81515
0.9141	High Similarity	NPC471157
0.913	High Similarity	NPC229505
0.9127	High Similarity	NPC52097
0.9124	High Similarity	NPC297342
0.9104	High Similarity	NPC78363
0.9104	High Similarity	NPC260425
0.907	High Similarity	NPC106677
0.9062	High Similarity	NPC126991
0.9062	High Similarity	NPC83218
0.9062	High Similarity	NPC90318
0.9058	High Similarity	NPC262182
0.9058	High Similarity	NPC83743
0.9058	High Similarity	NPC216819
0.9058	High Similarity	NPC287615
0.9048	High Similarity	NPC11724
0.9044	High Similarity	NPC476377
0.9044	High Similarity	NPC47471
0.9044	High Similarity	NPC134405
0.9044	High Similarity	NPC476385
0.9037	High Similarity	NPC205195
0.903	High Similarity	NPC37468
0.903	High Similarity	NPC186418
0.9015	High Similarity	NPC252833
0.9	High Similarity	NPC225307
0.8993	High Similarity	NPC473867
0.8992	High Similarity	NPC61181
0.8992	High Similarity	NPC252114
0.8978	High Similarity	NPC157816
0.8978	High Similarity	NPC140502
0.8978	High Similarity	NPC222433
0.8978	High Similarity	NPC265648
0.8971	High Similarity	NPC475530
0.8971	High Similarity	NPC473799
0.8971	High Similarity	NPC202700
0.8968	High Similarity	NPC476872
0.8947	High Similarity	NPC6836
0.8939	High Similarity	NPC281798
0.8939	High Similarity	NPC478255
0.8923	High Similarity	NPC103533
0.8913	High Similarity	NPC112
0.8913	High Similarity	NPC476384
0.8913	High Similarity	NPC478239
0.8913	High Similarity	NPC298257
0.8913	High Similarity	NPC476375
0.8913	High Similarity	NPC269141
0.8913	High Similarity	NPC264632
0.8913	High Similarity	NPC76406
0.8913	High Similarity	NPC476381
0.8913	High Similarity	NPC119537
0.8913	High Similarity	NPC96795
0.8913	High Similarity	NPC476378
0.8913	High Similarity	NPC205864
0.8913	High Similarity	NPC247032
0.8913	High Similarity	NPC175214
0.8913	High Similarity	NPC476380
0.8913	High Similarity	NPC476397
0.8905	High Similarity	NPC186406
0.8889	High Similarity	NPC471872
0.8889	High Similarity	NPC154485
0.8881	High Similarity	NPC470881
0.8873	High Similarity	NPC470934
0.8873	High Similarity	NPC188393
0.8865	High Similarity	NPC261122
0.8865	High Similarity	NPC201148
0.8865	High Similarity	NPC80732
0.8865	High Similarity	NPC28651
0.8865	High Similarity	NPC3460
0.8865	High Similarity	NPC192763
0.8865	High Similarity	NPC199311
0.8865	High Similarity	NPC210611
0.8865	High Similarity	NPC300262
0.8865	High Similarity	NPC215095
0.8849	High Similarity	NPC64195
0.8841	High Similarity	NPC296643
0.8803	High Similarity	NPC283839
0.8803	High Similarity	NPC90896
0.8794	High Similarity	NPC18789
0.8788	High Similarity	NPC307110
0.8786	High Similarity	NPC34927
0.8786	High Similarity	NPC252292
0.8786	High Similarity	NPC34587
0.8786	High Similarity	NPC100998
0.8786	High Similarity	NPC476382
0.8779	High Similarity	NPC288416
0.876	High Similarity	NPC224208
0.876	High Similarity	NPC474275
0.875	High Similarity	NPC266045
0.8723	High Similarity	NPC476865
0.8723	High Similarity	NPC199928
0.8714	High Similarity	NPC476867
0.8714	High Similarity	NPC292443
0.8714	High Similarity	NPC232228
0.8686	High Similarity	NPC195196
0.8681	High Similarity	NPC478249
0.8681	High Similarity	NPC143480
0.8681	High Similarity	NPC7145
0.8681	High Similarity	NPC269914
0.8681	High Similarity	NPC125823
0.8681	High Similarity	NPC85192
0.8676	High Similarity	NPC55040
0.8671	High Similarity	NPC478242
0.8667	High Similarity	NPC28637
0.8667	High Similarity	NPC25821
0.8662	High Similarity	NPC232992
0.8657	High Similarity	NPC65942
0.8657	High Similarity	NPC254819
0.8657	High Similarity	NPC225384
0.8657	High Similarity	NPC246869
0.8657	High Similarity	NPC248307
0.8657	High Similarity	NPC138777
0.8657	High Similarity	NPC235294
0.8657	High Similarity	NPC46137
0.8652	High Similarity	NPC476868
0.8652	High Similarity	NPC476864
0.8652	High Similarity	NPC476869
0.8652	High Similarity	NPC476866
0.8647	High Similarity	NPC253595
0.8621	High Similarity	NPC289967
0.8621	High Similarity	NPC472611
0.8621	High Similarity	NPC478268
0.8621	High Similarity	NPC472612
0.8611	High Similarity	NPC69367
0.8603	High Similarity	NPC135127
0.8601	High Similarity	NPC478237
0.8571	High Similarity	NPC281277
0.8562	High Similarity	NPC89693
0.8562	High Similarity	NPC229548
0.8562	High Similarity	NPC478241
0.8542	High Similarity	NPC476386
0.8542	High Similarity	NPC106138
0.8542	High Similarity	NPC473427
0.8542	High Similarity	NPC259347
0.8542	High Similarity	NPC94871
0.8542	High Similarity	NPC476398
0.8542	High Similarity	NPC470933
0.8542	High Similarity	NPC306890
0.8542	High Similarity	NPC471062
0.854	High Similarity	NPC185778
0.854	High Similarity	NPC123988
0.8529	High Similarity	NPC132895
0.8527	High Similarity	NPC476448
0.8527	High Similarity	NPC476445
0.8527	High Similarity	NPC469548
0.8507	High Similarity	NPC248355
0.8504	High Similarity	NPC65791
0.8496	Intermediate Similarity	NPC231607
0.8496	Intermediate Similarity	NPC264900
0.8496	Intermediate Similarity	NPC79715
0.8496	Intermediate Similarity	NPC108659
0.8493	Intermediate Similarity	NPC106818
0.8493	Intermediate Similarity	NPC203664
0.8492	Intermediate Similarity	NPC233669
0.8489	Intermediate Similarity	NPC49597
0.8483	Intermediate Similarity	NPC147224
0.8483	Intermediate Similarity	NPC257970
0.8483	Intermediate Similarity	NPC470927
0.8472	Intermediate Similarity	NPC23677

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 NPC254398 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	211
0.1-0.2	731
0.2-0.3	1683
0.3-0.4	2993
0.4-0.5	2011
0.5-0.6	1162
0.6-0.7	333
0.7-0.8	24
0.8-0.85	1
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9179	High Similarity	NPD7266	Discontinued
0.8288	Intermediate Similarity	NPD1653	Approved
0.8125	Intermediate Similarity	NPD6190	Approved
0.7716	Intermediate Similarity	NPD7685	Pre-registration
0.7687	Intermediate Similarity	NPD1357	Approved
0.7622	Intermediate Similarity	NPD230	Phase 1
0.7589	Intermediate Similarity	NPD3027	Phase 3
0.7536	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7533	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7518	Intermediate Similarity	NPD1091	Approved
0.7518	Intermediate Similarity	NPD3705	Approved
0.7469	Intermediate Similarity	NPD7228	Approved
0.7469	Intermediate Similarity	NPD3818	Discontinued
0.7468	Intermediate Similarity	NPD6234	Discontinued
0.7372	Intermediate Similarity	NPD37	Approved
0.7348	Intermediate Similarity	NPD969	Suspended
0.7342	Intermediate Similarity	NPD4967	Phase 2
0.7342	Intermediate Similarity	NPD4966	Approved
0.7342	Intermediate Similarity	NPD4965	Approved
0.7321	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD7054	Approved
0.731	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD1613	Approved
0.7273	Intermediate Similarity	NPD7472	Approved
0.7273	Intermediate Similarity	NPD7074	Phase 3
0.7246	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7233	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7229	Intermediate Similarity	NPD6797	Phase 2
0.7186	Intermediate Similarity	NPD6559	Discontinued
0.7186	Intermediate Similarity	NPD7251	Discontinued
0.7176	Intermediate Similarity	NPD1358	Approved
0.7161	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD8166	Discontinued
0.7101	Intermediate Similarity	NPD9545	Approved
0.709	Intermediate Similarity	NPD228	Approved
0.7081	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7068	Intermediate Similarity	NPD3022	Approved
0.7068	Intermediate Similarity	NPD3021	Approved
0.7055	Intermediate Similarity	NPD7199	Phase 2
0.7041	Intermediate Similarity	NPD7808	Phase 3
0.7039	Intermediate Similarity	NPD6674	Discontinued
0.7034	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7029	Intermediate Similarity	NPD5536	Phase 2
0.7013	Intermediate Similarity	NPD5058	Phase 3
0.7	Intermediate Similarity	NPD2978	Approved
0.7	Intermediate Similarity	NPD5126	Approved
0.7	Intermediate Similarity	NPD2977	Approved
0.7	Intermediate Similarity	NPD5125	Phase 3
0.6993	Remote Similarity	NPD4628	Phase 3
0.6982	Remote Similarity	NPD7240	Approved
0.6972	Remote Similarity	NPD9269	Phase 2
0.697	Remote Similarity	NPD3134	Approved
0.6966	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD9494	Approved
0.6962	Remote Similarity	NPD3455	Phase 2
0.6959	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6939	Remote Similarity	NPD3764	Approved
0.6937	Remote Similarity	NPD1934	Approved
0.6933	Remote Similarity	NPD4978	Clinical (unspecified phase)
0.6928	Remote Similarity	NPD1652	Phase 2
0.6914	Remote Similarity	NPD3882	Suspended
0.6894	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6894	Remote Similarity	NPD8455	Phase 2
0.6867	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD6653	Approved
0.6867	Remote Similarity	NPD2492	Phase 1
0.6846	Remote Similarity	NPD4060	Phase 1
0.6831	Remote Similarity	NPD3496	Discontinued
0.6826	Remote Similarity	NPD6166	Phase 2
0.6826	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6826	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6821	Remote Similarity	NPD7097	Phase 1
0.6806	Remote Similarity	NPD2983	Phase 2
0.6806	Remote Similarity	NPD2982	Phase 2
0.68	Remote Similarity	NPD5124	Phase 1
0.68	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6797	Remote Similarity	NPD2029	Clinical (unspecified phase)
0.6792	Remote Similarity	NPD3686	Approved
0.6792	Remote Similarity	NPD3687	Approved
0.6783	Remote Similarity	NPD422	Phase 1
0.6761	Remote Similarity	NPD9381	Approved
0.6761	Remote Similarity	NPD9384	Approved
0.6753	Remote Similarity	NPD2424	Discontinued
0.6752	Remote Similarity	NPD4357	Discontinued
0.6748	Remote Similarity	NPD3817	Phase 2
0.6747	Remote Similarity	NPD8127	Discontinued
0.6736	Remote Similarity	NPD2981	Phase 2
0.6735	Remote Similarity	NPD2861	Phase 2
0.6733	Remote Similarity	NPD825	Approved
0.6733	Remote Similarity	NPD3620	Phase 2
0.6733	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6733	Remote Similarity	NPD826	Approved
0.6732	Remote Similarity	NPD9570	Approved
0.6723	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6712	Remote Similarity	NPD3094	Phase 2
0.671	Remote Similarity	NPD4237	Approved
0.671	Remote Similarity	NPD4236	Phase 3
0.6708	Remote Similarity	NPD4380	Phase 2
0.6706	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6706	Remote Similarity	NPD5844	Phase 1
0.6705	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6705	Remote Similarity	NPD8313	Approved
0.6705	Remote Similarity	NPD8312	Approved
0.669	Remote Similarity	NPD9268	Approved
0.669	Remote Similarity	NPD9622	Approved
0.6689	Remote Similarity	NPD4340	Discontinued
0.6689	Remote Similarity	NPD447	Suspended
0.6688	Remote Similarity	NPD5762	Approved
0.6688	Remote Similarity	NPD1375	Discontinued
0.6688	Remote Similarity	NPD5763	Approved
0.6687	Remote Similarity	NPD2801	Approved
0.6685	Remote Similarity	NPD7237	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6233	Phase 2
0.6667	Remote Similarity	NPD7075	Discontinued
0.6667	Remote Similarity	NPD4110	Phase 3
0.6667	Remote Similarity	NPD7843	Approved
0.6648	Remote Similarity	NPD6843	Phase 3
0.6648	Remote Similarity	NPD6842	Approved
0.6648	Remote Similarity	NPD6841	Approved
0.6644	Remote Similarity	NPD7095	Approved
0.6643	Remote Similarity	NPD7157	Approved
0.6643	Remote Similarity	NPD4626	Approved
0.6642	Remote Similarity	NPD9280	Clinical (unspecified phase)
0.663	Remote Similarity	NPD7680	Approved
0.6623	Remote Similarity	NPD3062	Approved
0.6623	Remote Similarity	NPD3059	Approved
0.6623	Remote Similarity	NPD2935	Discontinued
0.6623	Remote Similarity	NPD3061	Approved
0.6622	Remote Similarity	NPD5736	Approved
0.6622	Remote Similarity	NPD3018	Phase 2
0.6619	Remote Similarity	NPD5283	Phase 1
0.6618	Remote Similarity	NPD2684	Approved
0.6605	Remote Similarity	NPD7028	Phase 2
0.6596	Remote Similarity	NPD694	Clinical (unspecified phase)
0.6591	Remote Similarity	NPD1242	Phase 1
0.6585	Remote Similarity	NPD5563	Clinical (unspecified phase)
0.6585	Remote Similarity	NPD1465	Phase 2
0.6579	Remote Similarity	NPD555	Phase 2
0.6579	Remote Similarity	NPD1933	Approved
0.6579	Remote Similarity	NPD6355	Discontinued
0.6573	Remote Similarity	NPD5691	Approved
0.6571	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6561	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6558	Remote Similarity	NPD7033	Discontinued
0.6558	Remote Similarity	NPD5588	Approved
0.6554	Remote Similarity	NPD9619	Approved
0.6554	Remote Similarity	NPD9620	Approved
0.6554	Remote Similarity	NPD9621	Approved
0.6552	Remote Similarity	NPD3092	Approved
0.655	Remote Similarity	NPD3751	Discontinued
0.6545	Remote Similarity	NPD5402	Approved
0.6545	Remote Similarity	NPD5353	Approved
0.6544	Remote Similarity	NPD290	Approved
0.6541	Remote Similarity	NPD5297	Approved
0.6541	Remote Similarity	NPD1511	Approved
0.6536	Remote Similarity	NPD5314	Approved
0.6528	Remote Similarity	NPD1778	Approved
0.6525	Remote Similarity	NPD6671	Approved
0.6513	Remote Similarity	NPD1558	Phase 1
0.6513	Remote Similarity	NPD4140	Approved
0.6513	Remote Similarity	NPD943	Approved
0.6509	Remote Similarity	NPD6232	Discontinued
0.65	Remote Similarity	NPD8389	Clinical (unspecified phase)
0.65	Remote Similarity	NPD4160	Clinical (unspecified phase)
0.6497	Remote Similarity	NPD3060	Approved
0.6497	Remote Similarity	NPD5698	Clinical (unspecified phase)
0.6494	Remote Similarity	NPD4538	Approved
0.6494	Remote Similarity	NPD4537	Clinical (unspecified phase)
0.6494	Remote Similarity	NPD4536	Approved
0.649	Remote Similarity	NPD597	Approved
0.649	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.649	Remote Similarity	NPD6798	Discontinued
0.649	Remote Similarity	NPD598	Approved
0.649	Remote Similarity	NPD601	Approved
0.6485	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6485	Remote Similarity	NPD5773	Approved
0.6485	Remote Similarity	NPD5772	Approved
0.6479	Remote Similarity	NPD9493	Approved
0.6474	Remote Similarity	NPD6005	Phase 3
0.6474	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6474	Remote Similarity	NPD6002	Phase 3
0.6474	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6474	Remote Similarity	NPD6004	Phase 3
0.6467	Remote Similarity	NPD4908	Phase 1
0.6467	Remote Similarity	NPD7975	Clinical (unspecified phase)
0.6463	Remote Similarity	NPD6385	Approved
0.6463	Remote Similarity	NPD6386	Approved
0.6462	Remote Similarity	NPD2934	Approved
0.6462	Remote Similarity	NPD2933	Approved
0.646	Remote Similarity	NPD1512	Approved
0.6457	Remote Similarity	NPD689	Discontinued
0.6457	Remote Similarity	NPD7549	Discontinued
0.6447	Remote Similarity	NPD1130	Approved
0.6447	Remote Similarity	NPD4062	Phase 3
0.6447	Remote Similarity	NPD1136	Approved
0.6447	Remote Similarity	NPD6663	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