NPASS Compound

Structure

NPC219677 OpenBabel07101718332D 35 37 0 0 1 0 0 0 0 0999 V2000 -8.2535 1.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.5215 1.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.1195 2.4135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6554 2.4135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.3875 3.4135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6386 -1.6637 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0574 1.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4593 1.4135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.3875 2.4135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.1195 3.4135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.2535 3.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7431 -0.6691 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.1913 2.4135 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.7894 1.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1913 3.4135 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6092 -0.1691 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.3253 3.9135 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.4593 3.4135 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.4013 0.8090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.4593 2.4135 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.4067 0.9135 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.4476 -2.2514 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3253 0.9135 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.9856 3.9135 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.2535 4.9135 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.7894 0.9135 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.0574 3.9135 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5227 -0.5759 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3253 4.9135 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.4067 3.9135 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.0704 1.5522 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.9234 2.4135 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3253 1.9135 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 0.4067 1.9135 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 3 2 0 0 0 0 1 9 1 0 0 0 0 2 4 2 0 0 0 0 2 9 1 0 0 0 0 3 10 1 0 0 0 0 4 14 1 0 0 0 0 5 9 2 0 0 0 0 5 11 1 0 0 0 0 6 22 1 0 0 0 0 7 32 1 0 0 0 0 8 23 1 0 0 0 0 10 11 2 0 0 0 0 10 24 1 0 0 0 0 11 25 1 0 0 0 0 12 6 1 1 0 0 0 12 16 1 0 0 0 0 12 34 1 0 0 0 0 13 7 1 6 0 0 0 13 15 1 0 0 0 0 13 33 1 0 0 0 0 14 26 2 0 0 0 0 14 32 1 0 0 0 0 15 17 1 0 0 0 0 15 27 1 1 0 0 0 16 19 1 0 0 0 0 16 28 1 6 0 0 0 17 18 1 0 0 0 0 17 29 1 6 0 0 0 18 20 1 0 0 0 0 18 30 1 1 0 0 0 19 21 1 1 0 0 0 19 31 1 0 0 0 0 20 33 1 0 0 0 0 20 35 1 1 0 0 0 21 8 1 6 0 0 0 21 34 1 0 0 0 0 21 35 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	504.15
Volume:	455.984
LogP:	-1.161
LogD:	-0.629
LogS:	-1.003
# Rotatable Bonds:	9
TPSA:	236.06
# H-Bond Aceptor:	14
# H-Bond Donor:	9
# Rings:	3
# Heavy Atoms:	14

MedChem Properties

QED Drug-Likeness Score:	0.094
Synthetic Accessibility Score:	4.607
Fsp3:	0.571
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.509
MDCK Permeability:	6.487951031886041e-05
Pgp-inhibitor:	0.002
Pgp-substrate:	0.979
Human Intestinal Absorption (HIA):	0.941
20% Bioavailability (F20%):	0.956
30% Bioavailability (F30%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.244
Plasma Protein Binding (PPB):	57.9188232421875%
Volume Distribution (VD):	0.396
Pgp-substrate:	45.27566909790039%

ADMET: Metabolism

CYP1A2-inhibitor:	0.027
CYP1A2-substrate:	0.029
CYP2C19-inhibitor:	0.02
CYP2C19-substrate:	0.053
CYP2C9-inhibitor:	0.002
CYP2C9-substrate:	0.077
CYP2D6-inhibitor:	0.002
CYP2D6-substrate:	0.133
CYP3A4-inhibitor:	0.019
CYP3A4-substrate:	0.017

ADMET: Excretion

Clearance (CL):	2.348
Half-life (T1/2):	0.907

ADMET: Toxicity

hERG Blockers:	0.249
Human Hepatotoxicity (H-HT):	0.062
Drug-inuced Liver Injury (DILI):	0.028
AMES Toxicity:	0.25
Rat Oral Acute Toxicity:	0.02
Maximum Recommended Daily Dose:	0.001
Skin Sensitization:	0.948
Carcinogencity:	0.115
Eye Corrosion:	0.003
Eye Irritation:	0.046
Respiratory Toxicity:	0.017

Download Data

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

Natural Product: NPC219677

Natural Product ID:	NPC219677
*Common Name:**	6-O-Caffeoyl-Beta-D-Fructofuranosyl-(2->1)-Alpha-D-Glucopyranoside
IUPAC Name:	[(2R,3S,4S,5R,6R)-6-[(2S,3S,4S,5R)-3,4-dihydroxy-2,5-bis(hydroxymethyl)oxolan-2-yl]oxy-3,4,5-trihydroxyoxan-2-yl]methyl (E)-3-(3,4-dihydroxyphenyl)prop-2-enoate
Synonyms:
Standard InCHIKey:	UZUDNVXQOKQTDO-WXOUDWAJSA-N
Standard InCHI:	InChI=1S/C21H28O14/c22-6-12-16(28)19(31)21(8-23,34-12)35-20-18(30)17(29)15(27)13(33-20)7-32-14(26)4-2-9-1-3-10(24)11(25)5-9/h1-5,12-13,15-20,22-25,27-31H,6-8H2/b4-2+/t12-,13-,15-,16-,17+,18-,19+,20-,21+/m1/s1
SMILES:	c1cc(c(cc1/C=C/C(=O)OC[C@@H]1[C@H]([C@@H]([C@H]([C@H](O1)O[C@@]1(CO)[C@H]([C@@H]([C@@H](CO)O1)O)O)O)O)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL455088
PubChem CID:	10346004
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
NPO6098	Salvia officinalis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10096857]
NPO6098	Salvia officinalis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23507152]
NPO6098	Salvia officinalis	Species	Lamiaceae	Eukaryota	Leaf Essent. Oil	n.a.	n.a.	Database[FooDB]
NPO6098	Salvia officinalis	Species	Lamiaceae	Eukaryota	Plant	n.a.	n.a.	Database[FooDB]
NPO6098	Salvia officinalis	Species	Lamiaceae	Eukaryota	Root	n.a.	n.a.	Database[FooDB]
NPO6098	Salvia officinalis	Species	Lamiaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO6098	Salvia officinalis	Species	Lamiaceae	Eukaryota	Shoot	n.a.	n.a.	Database[FooDB]
NPO6098	Salvia officinalis	Species	Lamiaceae	Eukaryota	Stem	n.a.	n.a.	Database[FooDB]
NPO6098	Salvia officinalis	Species	Lamiaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO6098	Salvia officinalis	Species	Lamiaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO6098	Salvia officinalis	Species	Lamiaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO6098	Salvia officinalis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO6098	Salvia officinalis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6098	Salvia officinalis	Species	Lamiaceae	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	1
Others	1

Activity Type	# Activity
NON-MOLECULAR	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	3.7	n.a.	PMID[484913]
NPT1	Others	Radical scavenging activity		IC50	=	20100.0	nM	PMID[484913]

☑ 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 NPC219677 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	286
0.1-0.2	1265
0.2-0.3	3301
0.3-0.4	8338
0.4-0.5	10175
0.5-0.6	7869
0.6-0.7	8678
0.7-0.8	2292
0.8-0.85	327
0.85-0.9	127
0.9-0.95	29
0.95-1	10

Similarity Score	Similarity Level	Natural Product ID
0.992	High Similarity	NPC473924
0.9841	High Similarity	NPC254398
0.9839	High Similarity	NPC477294
0.9839	High Similarity	NPC229784
0.9839	High Similarity	NPC477293
0.9764	High Similarity	NPC471883
0.9758	High Similarity	NPC232880
0.9677	High Similarity	NPC476873
0.9612	High Similarity	NPC470572
0.9606	High Similarity	NPC473285
0.9466	High Similarity	NPC171134
0.9466	High Similarity	NPC321184
0.9466	High Similarity	NPC321638
0.9466	High Similarity	NPC328273
0.9466	High Similarity	NPC220942
0.9466	High Similarity	NPC226005
0.9457	High Similarity	NPC886
0.9457	High Similarity	NPC287597
0.9457	High Similarity	NPC34293
0.9385	High Similarity	NPC476870
0.9313	High Similarity	NPC157554
0.9274	High Similarity	NPC52097
0.9242	High Similarity	NPC476376
0.9242	High Similarity	NPC78363
0.9242	High Similarity	NPC260425
0.9213	High Similarity	NPC471882
0.9213	High Similarity	NPC156692
0.9213	High Similarity	NPC173150
0.9213	High Similarity	NPC35288
0.9213	High Similarity	NPC45224
0.9213	High Similarity	NPC471881
0.9206	High Similarity	NPC126991
0.9206	High Similarity	NPC83218
0.9194	High Similarity	NPC11724
0.9185	High Similarity	NPC40305
0.9185	High Similarity	NPC105005
0.9173	High Similarity	NPC205195
0.9173	High Similarity	NPC476383
0.9173	High Similarity	NPC68092
0.9173	High Similarity	NPC197316
0.9173	High Similarity	NPC64141
0.9173	High Similarity	NPC100389
0.9173	High Similarity	NPC472350
0.9173	High Similarity	NPC89105
0.9173	High Similarity	NPC81515
0.9167	High Similarity	NPC186418
0.9141	High Similarity	NPC225307
0.9134	High Similarity	NPC471157
0.9118	High Similarity	NPC196063
0.9118	High Similarity	NPC110063
0.9118	High Similarity	NPC297342
0.9118	High Similarity	NPC296954
0.9118	High Similarity	NPC300894
0.9118	High Similarity	NPC141455
0.9113	High Similarity	NPC476872
0.9104	High Similarity	NPC202700
0.9055	High Similarity	NPC90318
0.9051	High Similarity	NPC83743
0.9051	High Similarity	NPC216819
0.9051	High Similarity	NPC262182
0.9051	High Similarity	NPC287615
0.9037	High Similarity	NPC476385
0.9037	High Similarity	NPC186406
0.9037	High Similarity	NPC476377
0.9037	High Similarity	NPC47471
0.9037	High Similarity	NPC134405
0.9023	High Similarity	NPC37468
0.8986	High Similarity	NPC473867
0.8986	High Similarity	NPC229505
0.8984	High Similarity	NPC61181
0.8984	High Similarity	NPC252114
0.8971	High Similarity	NPC157816
0.8971	High Similarity	NPC140502
0.8971	High Similarity	NPC265648
0.8971	High Similarity	NPC222433
0.8963	High Similarity	NPC473799
0.8963	High Similarity	NPC475530
0.8931	High Similarity	NPC281798
0.8931	High Similarity	NPC478255
0.8915	High Similarity	NPC106677
0.8915	High Similarity	NPC103533
0.8915	High Similarity	NPC288416
0.8905	High Similarity	NPC76406
0.8905	High Similarity	NPC119537
0.8905	High Similarity	NPC478239
0.8905	High Similarity	NPC96795
0.8905	High Similarity	NPC476378
0.8905	High Similarity	NPC247032
0.8905	High Similarity	NPC298257
0.8905	High Similarity	NPC205864
0.8905	High Similarity	NPC476380
0.8905	High Similarity	NPC476397
0.8905	High Similarity	NPC476384
0.8905	High Similarity	NPC476381
0.8905	High Similarity	NPC476375
0.8905	High Similarity	NPC175214
0.8905	High Similarity	NPC112
0.8905	High Similarity	NPC269141
0.8905	High Similarity	NPC264632
0.8898	High Similarity	NPC224208
0.8898	High Similarity	NPC474275
0.8889	High Similarity	NPC266045
0.8881	High Similarity	NPC471872
0.8881	High Similarity	NPC154485
0.8864	High Similarity	NPC252833
0.8857	High Similarity	NPC192763
0.8857	High Similarity	NPC3460
0.8857	High Similarity	NPC215095
0.8857	High Similarity	NPC199311
0.8857	High Similarity	NPC210611
0.8857	High Similarity	NPC300262
0.8857	High Similarity	NPC261122
0.8857	High Similarity	NPC80732
0.8857	High Similarity	NPC201148
0.8857	High Similarity	NPC28651
0.8841	High Similarity	NPC232228
0.8841	High Similarity	NPC64195
0.8841	High Similarity	NPC476867
0.8841	High Similarity	NPC292443
0.8832	High Similarity	NPC296643
0.8797	High Similarity	NPC6836
0.8797	High Similarity	NPC28637
0.8794	High Similarity	NPC90896
0.8794	High Similarity	NPC283839
0.8788	High Similarity	NPC254819
0.8786	High Similarity	NPC18789
0.8779	High Similarity	NPC253595
0.8779	High Similarity	NPC307110
0.8777	High Similarity	NPC252292
0.8777	High Similarity	NPC100998
0.8777	High Similarity	NPC34587
0.8777	High Similarity	NPC476864
0.8777	High Similarity	NPC476382
0.8777	High Similarity	NPC476866
0.8777	High Similarity	NPC34927
0.8777	High Similarity	NPC476869
0.8777	High Similarity	NPC476868
0.8732	High Similarity	NPC470934
0.8732	High Similarity	NPC188393
0.8731	High Similarity	NPC470881
0.8714	High Similarity	NPC476865
0.8714	High Similarity	NPC199928
0.8671	High Similarity	NPC125823
0.8671	High Similarity	NPC7145
0.8671	High Similarity	NPC85192
0.8671	High Similarity	NPC143480
0.8667	High Similarity	NPC55040
0.8667	High Similarity	NPC123988
0.8652	High Similarity	NPC232992
0.8647	High Similarity	NPC235294
0.8647	High Similarity	NPC46137
0.8647	High Similarity	NPC225384
0.8647	High Similarity	NPC65942
0.8647	High Similarity	NPC246869
0.8647	High Similarity	NPC248307
0.8647	High Similarity	NPC138777
0.8626	High Similarity	NPC231607
0.8626	High Similarity	NPC79715
0.8626	High Similarity	NPC264900
0.8626	High Similarity	NPC108659
0.8611	High Similarity	NPC472611
0.8611	High Similarity	NPC478268
0.8611	High Similarity	NPC472612
0.8611	High Similarity	NPC289967
0.8601	High Similarity	NPC69367
0.8594	High Similarity	NPC147654
0.8593	High Similarity	NPC135127
0.8593	High Similarity	NPC474895
0.8592	High Similarity	NPC478237
0.8582	High Similarity	NPC254275
0.8561	High Similarity	NPC148982
0.856	High Similarity	NPC281277
0.855	High Similarity	NPC94179
0.8548	High Similarity	NPC217472
0.8548	High Similarity	NPC313193
0.8542	High Similarity	NPC269914
0.8542	High Similarity	NPC478249
0.854	High Similarity	NPC100558
0.854	High Similarity	NPC310252
0.854	High Similarity	NPC195196
0.854	High Similarity	NPC302583
0.854	High Similarity	NPC84789
0.8531	High Similarity	NPC259347
0.8531	High Similarity	NPC306890
0.8531	High Similarity	NPC94871
0.8531	High Similarity	NPC476398
0.8531	High Similarity	NPC470933
0.8531	High Similarity	NPC478242
0.8531	High Similarity	NPC471062
0.8531	High Similarity	NPC106138
0.8531	High Similarity	NPC476386
0.8531	High Similarity	NPC473427
0.8529	High Similarity	NPC185778
0.8521	High Similarity	NPC41844
0.8519	High Similarity	NPC25821
0.8519	High Similarity	NPC132895
0.8511	High Similarity	NPC108455
0.8496	Intermediate Similarity	NPC248355
0.8496	Intermediate Similarity	NPC184092
0.8492	Intermediate Similarity	NPC65791

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 NPC219677 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	227
0.1-0.2	738
0.2-0.3	1707
0.3-0.4	3025
0.4-0.5	1959
0.5-0.6	1132
0.6-0.7	337
0.7-0.8	23
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
0.9173	High Similarity	NPD7266	Discontinued
0.8403	Intermediate Similarity	NPD1653	Approved
0.8112	Intermediate Similarity	NPD6190	Approved
0.7669	Intermediate Similarity	NPD1357	Approved
0.763	Intermediate Similarity	NPD1091	Approved
0.7606	Intermediate Similarity	NPD230	Phase 1
0.7593	Intermediate Similarity	NPD7685	Pre-registration
0.7571	Intermediate Similarity	NPD3027	Phase 3
0.7562	Intermediate Similarity	NPD3818	Discontinued
0.7518	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7517	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD3705	Approved
0.7462	Intermediate Similarity	NPD969	Suspended
0.7453	Intermediate Similarity	NPD7228	Approved
0.7452	Intermediate Similarity	NPD6234	Discontinued
0.7413	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7413	Intermediate Similarity	NPD1613	Approved
0.7355	Intermediate Similarity	NPD37	Approved
0.7333	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7325	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7325	Intermediate Similarity	NPD4966	Approved
0.7325	Intermediate Similarity	NPD4967	Phase 2
0.7325	Intermediate Similarity	NPD4965	Approved
0.7301	Intermediate Similarity	NPD7054	Approved
0.7256	Intermediate Similarity	NPD7074	Phase 3
0.7256	Intermediate Similarity	NPD7472	Approved
0.7212	Intermediate Similarity	NPD6797	Phase 2
0.7202	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7169	Intermediate Similarity	NPD7251	Discontinued
0.7169	Intermediate Similarity	NPD6559	Discontinued
0.7154	Intermediate Similarity	NPD1358	Approved
0.7143	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD8166	Discontinued
0.708	Intermediate Similarity	NPD9545	Approved
0.7071	Intermediate Similarity	NPD9269	Phase 2
0.7068	Intermediate Similarity	NPD228	Approved
0.7063	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7045	Intermediate Similarity	NPD3021	Approved
0.7045	Intermediate Similarity	NPD3022	Approved
0.7037	Intermediate Similarity	NPD7199	Phase 2
0.7027	Intermediate Similarity	NPD4978	Clinical (unspecified phase)
0.7024	Intermediate Similarity	NPD7808	Phase 3
0.702	Intermediate Similarity	NPD6674	Discontinued
0.7007	Intermediate Similarity	NPD5536	Phase 2
0.6981	Remote Similarity	NPD8455	Phase 2
0.6981	Remote Similarity	NPD2977	Approved
0.6981	Remote Similarity	NPD2978	Approved
0.6978	Remote Similarity	NPD5126	Approved
0.6978	Remote Similarity	NPD5125	Phase 3
0.6974	Remote Similarity	NPD4628	Phase 3
0.6964	Remote Similarity	NPD7240	Approved
0.6959	Remote Similarity	NPD2492	Phase 1
0.6947	Remote Similarity	NPD3134	Approved
0.6944	Remote Similarity	NPD9494	Approved
0.6943	Remote Similarity	NPD3455	Phase 2
0.6918	Remote Similarity	NPD1934	Approved
0.6918	Remote Similarity	NPD3764	Approved
0.6908	Remote Similarity	NPD1652	Phase 2
0.6905	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6894	Remote Similarity	NPD3882	Suspended
0.6887	Remote Similarity	NPD2029	Clinical (unspecified phase)
0.6883	Remote Similarity	NPD5058	Phase 3
0.6875	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD9384	Approved
0.6857	Remote Similarity	NPD9381	Approved
0.6848	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6846	Remote Similarity	NPD6653	Approved
0.6828	Remote Similarity	NPD2861	Phase 2
0.6824	Remote Similarity	NPD4060	Phase 1
0.6824	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6821	Remote Similarity	NPD9570	Approved
0.6809	Remote Similarity	NPD3496	Discontinued
0.6807	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6807	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6807	Remote Similarity	NPD6166	Phase 2
0.6792	Remote Similarity	NPD4380	Phase 2
0.6786	Remote Similarity	NPD9268	Approved
0.6784	Remote Similarity	NPD8313	Approved
0.6784	Remote Similarity	NPD8312	Approved
0.6783	Remote Similarity	NPD2983	Phase 2
0.6783	Remote Similarity	NPD2982	Phase 2
0.6779	Remote Similarity	NPD4340	Discontinued
0.6772	Remote Similarity	NPD3686	Approved
0.6772	Remote Similarity	NPD3687	Approved
0.6761	Remote Similarity	NPD422	Phase 1
0.6741	Remote Similarity	NPD9280	Clinical (unspecified phase)
0.6731	Remote Similarity	NPD4357	Discontinued
0.6728	Remote Similarity	NPD3817	Phase 2
0.6727	Remote Similarity	NPD8127	Discontinued
0.6713	Remote Similarity	NPD2981	Phase 2
0.6711	Remote Similarity	NPD3059	Approved
0.6711	Remote Similarity	NPD3062	Approved
0.6711	Remote Similarity	NPD826	Approved
0.6711	Remote Similarity	NPD3061	Approved
0.6711	Remote Similarity	NPD825	Approved
0.6711	Remote Similarity	NPD3620	Phase 2
0.6711	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6692	Remote Similarity	NPD1242	Phase 1
0.669	Remote Similarity	NPD3094	Phase 2
0.6689	Remote Similarity	NPD7097	Phase 1
0.6688	Remote Similarity	NPD4236	Phase 3
0.6688	Remote Similarity	NPD4237	Approved
0.6686	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6686	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6686	Remote Similarity	NPD5844	Phase 1
0.6667	Remote Similarity	NPD7237	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD2801	Approved
0.6667	Remote Similarity	NPD447	Suspended
0.6667	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5763	Approved
0.6667	Remote Similarity	NPD5762	Approved
0.6667	Remote Similarity	NPD9622	Approved
0.6667	Remote Similarity	NPD5124	Phase 1
0.6667	Remote Similarity	NPD1465	Phase 2
0.6646	Remote Similarity	NPD7075	Discontinued
0.6645	Remote Similarity	NPD4110	Phase 3
0.6645	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6645	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6645	Remote Similarity	NPD5588	Approved
0.6644	Remote Similarity	NPD6233	Phase 2
0.6642	Remote Similarity	NPD7843	Approved
0.6629	Remote Similarity	NPD6841	Approved
0.6629	Remote Similarity	NPD6842	Approved
0.6629	Remote Similarity	NPD6843	Phase 3
0.6626	Remote Similarity	NPD5402	Approved
0.6624	Remote Similarity	NPD1511	Approved
0.6623	Remote Similarity	NPD5314	Approved
0.6623	Remote Similarity	NPD2424	Discontinued
0.662	Remote Similarity	NPD4626	Approved
0.6619	Remote Similarity	NPD7157	Approved
0.6612	Remote Similarity	NPD7680	Approved
0.661	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6601	Remote Similarity	NPD2935	Discontinued
0.66	Remote Similarity	NPD943	Approved
0.6599	Remote Similarity	NPD3018	Phase 2
0.6599	Remote Similarity	NPD5736	Approved
0.6594	Remote Similarity	NPD5283	Phase 1
0.6593	Remote Similarity	NPD2684	Approved
0.6582	Remote Similarity	NPD4160	Clinical (unspecified phase)
0.6571	Remote Similarity	NPD694	Clinical (unspecified phase)
0.6564	Remote Similarity	NPD5563	Clinical (unspecified phase)
0.656	Remote Similarity	NPD689	Discontinued
0.6558	Remote Similarity	NPD1375	Discontinued
0.6556	Remote Similarity	NPD6355	Discontinued
0.6556	Remote Similarity	NPD555	Phase 2
0.6556	Remote Similarity	NPD1933	Approved
0.6552	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6549	Remote Similarity	NPD5691	Approved
0.6541	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.6541	Remote Similarity	NPD1512	Approved
0.6531	Remote Similarity	NPD9621	Approved
0.6531	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6531	Remote Similarity	NPD9619	Approved
0.6531	Remote Similarity	NPD9620	Approved
0.6529	Remote Similarity	NPD3751	Discontinued
0.6528	Remote Similarity	NPD3092	Approved
0.6524	Remote Similarity	NPD5353	Approved
0.6519	Remote Similarity	NPD290	Approved
0.6519	Remote Similarity	NPD5297	Approved
0.6519	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.6513	Remote Similarity	NPD817	Approved
0.6513	Remote Similarity	NPD823	Approved
0.651	Remote Similarity	NPD7095	Approved
0.6503	Remote Similarity	NPD1778	Approved
0.65	Remote Similarity	NPD5403	Approved
0.649	Remote Similarity	NPD4140	Approved
0.649	Remote Similarity	NPD1558	Phase 1
0.6488	Remote Similarity	NPD6232	Discontinued
0.6481	Remote Similarity	NPD7028	Phase 2
0.6478	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6474	Remote Similarity	NPD5698	Clinical (unspecified phase)
0.6474	Remote Similarity	NPD3060	Approved
0.6471	Remote Similarity	NPD4538	Approved
0.6471	Remote Similarity	NPD4537	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD4536	Approved
0.6467	Remote Similarity	NPD6798	Discontinued
0.6467	Remote Similarity	NPD597	Approved
0.6467	Remote Similarity	NPD598	Approved
0.6467	Remote Similarity	NPD601	Approved
0.6467	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6463	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6463	Remote Similarity	NPD5773	Approved
0.6463	Remote Similarity	NPD5772	Approved
0.6454	Remote Similarity	NPD9493	Approved
0.6452	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6452	Remote Similarity	NPD6002	Phase 3
0.6452	Remote Similarity	NPD6004	Phase 3
0.6452	Remote Similarity	NPD6005	Phase 3
0.6452	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6443	Remote Similarity	NPD4908	Phase 1
0.6442	Remote Similarity	NPD6385	Approved
0.6442	Remote Similarity	NPD6386	Approved
0.6434	Remote Similarity	NPD2933	Approved
0.6434	Remote Similarity	NPD2934	Approved
0.6433	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD651	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD5960	Phase 3
0.6429	Remote Similarity	NPD7033	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