NPASS Compound

Structure

NPC208797 OpenBabel07101718322D 40 45 0 0 1 0 0 0 0 0999 V2000 -4.7709 -4.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7709 -2.6340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7709 -4.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7709 -2.6340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -7.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6831 -2.6910 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 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2709 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.2709 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -7.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2709 -3.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -4.0000 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 -0.8660 -5.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -7.0000 0.0000 C 0 0 0 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 -6.0000 0.0000 C 0 0 0 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 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -5.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 C 0 0 2 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 -7.2709 -3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -8.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -7.5000 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 -5.5000 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 -6.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.6831 -4.3090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -4.5000 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 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 3 1 0 0 0 0 1 9 2 0 0 0 0 2 4 2 0 0 0 0 2 9 1 0 0 0 0 3 10 2 0 0 0 0 4 10 1 0 0 0 0 5 12 2 0 0 0 0 5 13 1 0 0 0 0 6 11 1 0 0 0 0 6 14 1 0 0 0 0 7 15 2 0 0 0 0 7 16 1 0 0 0 0 8 28 1 0 0 0 0 10 29 1 0 0 0 0 11 15 1 0 0 0 0 11 25 2 0 0 0 0 12 18 1 0 0 0 0 12 26 1 0 0 0 0 13 20 2 0 0 0 0 13 30 1 0 0 0 0 14 9 1 1 0 0 0 14 37 1 0 0 0 0 15 39 1 0 0 0 0 16 19 2 0 0 0 0 16 38 1 0 0 0 0 17 8 1 6 0 0 0 17 21 1 0 0 0 0 17 40 1 0 0 0 0 18 19 1 0 0 0 0 18 22 2 0 0 0 0 19 25 1 0 0 0 0 20 22 1 0 0 0 0 20 31 1 0 0 0 0 21 23 1 0 0 0 0 21 32 1 1 0 0 0 22 33 1 0 0 0 0 23 24 1 0 0 0 0 23 34 1 6 0 0 0 24 27 1 0 0 0 0 24 35 1 1 0 0 0 25 37 1 0 0 0 0 26 36 2 0 0 0 0 26 38 1 0 0 0 0 27 39 1 6 0 0 0 27 40 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	556.12
Volume:	512.118
LogP:	0.872
LogD:	0.119
LogS:	-4.624
# Rotatable Bonds:	4
TPSA:	219.74
# H-Bond Aceptor:	13
# H-Bond Donor:	8
# Rings:	6
# Heavy Atoms:	13

MedChem Properties

QED Drug-Likeness Score:	0.098
Synthetic Accessibility Score:	4.587
Fsp3:	0.296
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:	-6.484
MDCK Permeability:	6.134333943919046e-06
Pgp-inhibitor:	0.03
Pgp-substrate:	0.829
Human Intestinal Absorption (HIA):	0.708
20% Bioavailability (F20%):	0.018
30% Bioavailability (F30%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.01
Plasma Protein Binding (PPB):	94.59803009033203%
Volume Distribution (VD):	0.547
Pgp-substrate:	15.637950897216797%

ADMET: Metabolism

CYP1A2-inhibitor:	0.08
CYP1A2-substrate:	0.061
CYP2C19-inhibitor:	0.016
CYP2C19-substrate:	0.055
CYP2C9-inhibitor:	0.274
CYP2C9-substrate:	0.28
CYP2D6-inhibitor:	0.048
CYP2D6-substrate:	0.163
CYP3A4-inhibitor:	0.042
CYP3A4-substrate:	0.017

ADMET: Excretion

Clearance (CL):	2.708
Half-life (T1/2):	0.771

ADMET: Toxicity

hERG Blockers:	0.156
Human Hepatotoxicity (H-HT):	0.728
Drug-inuced Liver Injury (DILI):	0.979
AMES Toxicity:	0.591
Rat Oral Acute Toxicity:	0.163
Maximum Recommended Daily Dose:	0.059
Skin Sensitization:	0.949
Carcinogencity:	0.335
Eye Corrosion:	0.003
Eye Irritation:	0.416
Respiratory Toxicity:	0.022

Download Data

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

Natural Product: NPC208797

Natural Product ID:	NPC208797
*Common Name:**	(R)-2-(4-Hydroxyphenyl)-9,10,11-Trihydroxy-2H-Benzo[C]Furo[2,3-F]Chromen-7(3H)-One-4-O-Beta-D-Glucopyranoside
IUPAC Name:	(2R)-9,10,11-trihydroxy-2-(4-hydroxyphenyl)-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2,3-dihydro-[1]benzofuro[6,7-c]isochromen-7-one
Synonyms:
Standard InCHIKey:	BNHQQRPAHBTLKE-BSGODVDVSA-N
Standard InCHI:	InChI=1S/C27H24O13/c28-8-17-21(32)23(34)24(35)27(40-17)39-15-7-16-19(18-12(26(36)38-16)5-13(30)20(31)22(18)33)25-11(15)6-14(37-25)9-1-3-10(29)4-2-9/h1-5,7,14,17,21,23-24,27-35H,6,8H2/t14-,17-,21-,23+,24-,27-/m1/s1
SMILES:	OC[C@H]1O[C@@H](Oc2cc3oc(=O)c4c(c3c3c2C[C@@H](O3)c2ccc(cc2)O)c(O)c(c(c4)O)O)[C@@H]([C@H]([C@@H]1O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3109431
PubChem CID:	76328405
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0003405] 2-arylbenzofuran flavonoids

*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
NPO31520	Polygonum multiflorum	Species	Polygonaceae	Eukaryota	roots	n.a.	n.a.	PMID[24499304]
NPO31520	Polygonum multiflorum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO31520	Polygonum multiflorum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]

☑ 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

Activity Type	# Activity
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1	Others	Radical scavenging activity		IC50	=	569000.0	nM	PMID[523668]

☑ 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 NPC208797 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	460
0.1-0.2	1844
0.2-0.3	3859
0.3-0.4	8973
0.4-0.5	9182
0.5-0.6	4530
0.6-0.7	5292
0.7-0.8	5649
0.8-0.85	1911
0.85-0.9	854
0.9-0.95	141
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC53680
0.9583	High Similarity	NPC297574
0.936	High Similarity	NPC129533
0.936	High Similarity	NPC123259
0.9357	High Similarity	NPC80956
0.9353	High Similarity	NPC79736
0.9353	High Similarity	NPC67629
0.9349	High Similarity	NPC46640
0.9349	High Similarity	NPC263119
0.9349	High Similarity	NPC34436
0.9349	High Similarity	NPC166674
0.9349	High Similarity	NPC219600
0.9345	High Similarity	NPC181778
0.9298	High Similarity	NPC267549
0.929	High Similarity	NPC38438
0.9277	High Similarity	NPC121290
0.9261	High Similarity	NPC264302
0.9257	High Similarity	NPC269046
0.924	High Similarity	NPC473713
0.9235	High Similarity	NPC473550
0.92	High Similarity	NPC105591
0.92	High Similarity	NPC237202
0.9195	High Similarity	NPC231254
0.9191	High Similarity	NPC8940
0.9181	High Similarity	NPC193377
0.9176	High Similarity	NPC67134
0.9176	High Similarity	NPC47140
0.9148	High Similarity	NPC119094
0.9148	High Similarity	NPC173872
0.9128	High Similarity	NPC472723
0.9123	High Similarity	NPC316539
0.9118	High Similarity	NPC52598
0.9112	High Similarity	NPC473818
0.9102	High Similarity	NPC14030
0.9102	High Similarity	NPC291957
0.9096	High Similarity	NPC289346
0.9096	High Similarity	NPC24164
0.9091	High Similarity	NPC65489
0.908	High Similarity	NPC469371
0.9075	High Similarity	NPC476619
0.9075	High Similarity	NPC476623
0.9075	High Similarity	NPC476621
0.9075	High Similarity	NPC476622
0.9075	High Similarity	NPC476620
0.9075	High Similarity	NPC476618
0.905	High Similarity	NPC476358
0.905	High Similarity	NPC477082
0.9048	High Similarity	NPC470898
0.904	High Similarity	NPC477083
0.904	High Similarity	NPC142291
0.904	High Similarity	NPC7839
0.904	High Similarity	NPC477081
0.9034	High Similarity	NPC261623
0.9034	High Similarity	NPC111490
0.9006	High Similarity	NPC204937
0.9006	High Similarity	NPC149011
0.9	High Similarity	NPC470271
0.9	High Similarity	NPC311389
0.8989	High Similarity	NPC469652
0.8989	High Similarity	NPC472724
0.8989	High Similarity	NPC472721
0.8989	High Similarity	NPC93065
0.8989	High Similarity	NPC31208
0.8989	High Similarity	NPC472720
0.8989	High Similarity	NPC160543
0.8988	High Similarity	NPC33298
0.8988	High Similarity	NPC4013
0.8988	High Similarity	NPC90905
0.8988	High Similarity	NPC285108
0.8976	High Similarity	NPC114179
0.8976	High Similarity	NPC156818
0.8976	High Similarity	NPC160512
0.8976	High Similarity	NPC68324
0.8976	High Similarity	NPC289322
0.8976	High Similarity	NPC38779
0.8971	High Similarity	NPC125352
0.8971	High Similarity	NPC170203
0.8971	High Similarity	NPC475161
0.8971	High Similarity	NPC477860
0.8966	High Similarity	NPC476773
0.8966	High Similarity	NPC472387
0.896	High Similarity	NPC3718
0.8953	High Similarity	NPC262580
0.8953	High Similarity	NPC20114
0.8953	High Similarity	NPC474075
0.8953	High Similarity	NPC289396
0.8953	High Similarity	NPC312006
0.8953	High Similarity	NPC471920
0.8953	High Similarity	NPC114550
0.8953	High Similarity	NPC471921
0.8953	High Similarity	NPC129930
0.8953	High Similarity	NPC65333
0.8953	High Similarity	NPC471922
0.8953	High Similarity	NPC271848
0.8953	High Similarity	NPC212038
0.8953	High Similarity	NPC292712
0.8953	High Similarity	NPC81332
0.8947	High Similarity	NPC197708
0.8947	High Similarity	NPC658
0.8941	High Similarity	NPC175793
0.8935	High Similarity	NPC67959
0.8933	High Similarity	NPC223534
0.8933	High Similarity	NPC158214
0.8933	High Similarity	NPC240200
0.8933	High Similarity	NPC290289
0.8927	High Similarity	NPC469650
0.8922	High Similarity	NPC24339
0.8922	High Similarity	NPC94220
0.8922	High Similarity	NPC7543
0.8922	High Similarity	NPC98083
0.8922	High Similarity	NPC166456
0.892	High Similarity	NPC132111
0.8916	High Similarity	NPC104983
0.8916	High Similarity	NPC291948
0.8916	High Similarity	NPC318432
0.8916	High Similarity	NPC250436
0.8916	High Similarity	NPC300845
0.8916	High Similarity	NPC88803
0.8914	High Similarity	NPC212290
0.8914	High Similarity	NPC275690
0.8914	High Similarity	NPC299149
0.8914	High Similarity	NPC153578
0.8914	High Similarity	NPC277710
0.8914	High Similarity	NPC161609
0.8914	High Similarity	NPC114257
0.8908	High Similarity	NPC144097
0.8908	High Similarity	NPC472991
0.8908	High Similarity	NPC475246
0.8908	High Similarity	NPC61904
0.8908	High Similarity	NPC296018
0.8908	High Similarity	NPC154741
0.8908	High Similarity	NPC196771
0.8908	High Similarity	NPC472992
0.8902	High Similarity	NPC98583
0.8902	High Similarity	NPC163165
0.8902	High Similarity	NPC172033
0.8902	High Similarity	NPC472993
0.8902	High Similarity	NPC88560
0.8902	High Similarity	NPC175230
0.8895	High Similarity	NPC78734
0.8895	High Similarity	NPC470272
0.8895	High Similarity	NPC218488
0.8895	High Similarity	NPC313304
0.8895	High Similarity	NPC150767
0.8889	High Similarity	NPC190204
0.8889	High Similarity	NPC43918
0.8889	High Similarity	NPC45400
0.8889	High Similarity	NPC311912
0.8889	High Similarity	NPC298847
0.8889	High Similarity	NPC261411
0.8883	High Similarity	NPC201814
0.8883	High Similarity	NPC187632
0.8876	High Similarity	NPC469649
0.8876	High Similarity	NPC260521
0.8876	High Similarity	NPC22324
0.8876	High Similarity	NPC179947
0.887	High Similarity	NPC49690
0.8869	High Similarity	NPC203020
0.8869	High Similarity	NPC53889
0.8869	High Similarity	NPC24627
0.8869	High Similarity	NPC239966
0.8857	High Similarity	NPC35167
0.8857	High Similarity	NPC253521
0.8857	High Similarity	NPC37668
0.8857	High Similarity	NPC47191
0.8857	High Similarity	NPC113836
0.8851	High Similarity	NPC472607
0.8851	High Similarity	NPC84482
0.8851	High Similarity	NPC81042
0.8851	High Similarity	NPC169645
0.8851	High Similarity	NPC223426
0.8851	High Similarity	NPC214621
0.8851	High Similarity	NPC63105
0.8851	High Similarity	NPC34267
0.8851	High Similarity	NPC68381
0.8844	High Similarity	NPC100251
0.8844	High Similarity	NPC102851
0.8844	High Similarity	NPC5786
0.8844	High Similarity	NPC256760
0.8837	High Similarity	NPC117911
0.8837	High Similarity	NPC222455
0.8837	High Similarity	NPC229687
0.8837	High Similarity	NPC95421
0.8837	High Similarity	NPC198125
0.8837	High Similarity	NPC88557
0.8833	High Similarity	NPC471091
0.8833	High Similarity	NPC97924
0.8833	High Similarity	NPC40078
0.8827	High Similarity	NPC473618
0.8827	High Similarity	NPC205721
0.8824	High Similarity	NPC29830
0.882	High Similarity	NPC241847
0.882	High Similarity	NPC87583
0.8817	High Similarity	NPC109061
0.8817	High Similarity	NPC139540
0.8817	High Similarity	NPC177100
0.8814	High Similarity	NPC321916
0.8814	High Similarity	NPC35924
0.8814	High Similarity	NPC199172
0.881	High Similarity	NPC40702

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 NPC208797 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	401
0.1-0.2	950
0.2-0.3	1966
0.3-0.4	2664
0.4-0.5	1864
0.5-0.6	850
0.6-0.7	281
0.7-0.8	132
0.8-0.85	24
0.85-0.9	18
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8916	High Similarity	NPD4868	Clinical (unspecified phase)
0.8837	High Similarity	NPD5844	Phase 1
0.8779	High Similarity	NPD3818	Discontinued
0.8683	High Similarity	NPD1465	Phase 2
0.8678	High Similarity	NPD7074	Phase 3
0.8671	High Similarity	NPD7228	Approved
0.8629	High Similarity	NPD7993	Clinical (unspecified phase)
0.8621	High Similarity	NPD7054	Approved
0.8571	High Similarity	NPD7472	Approved
0.8531	High Similarity	NPD4338	Clinical (unspecified phase)
0.8523	High Similarity	NPD6797	Phase 2
0.8475	Intermediate Similarity	NPD6559	Discontinued
0.8475	Intermediate Similarity	NPD7251	Discontinued
0.8448	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8448	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8448	Intermediate Similarity	NPD6166	Phase 2
0.8421	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8382	Intermediate Similarity	NPD7199	Phase 2
0.838	Intermediate Similarity	NPD8312	Approved
0.838	Intermediate Similarity	NPD8313	Approved
0.8372	Intermediate Similarity	NPD6234	Discontinued
0.8333	Intermediate Similarity	NPD6232	Discontinued
0.8324	Intermediate Similarity	NPD7808	Phase 3
0.8305	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8294	Intermediate Similarity	NPD37	Approved
0.8256	Intermediate Similarity	NPD4966	Approved
0.8256	Intermediate Similarity	NPD4965	Approved
0.8256	Intermediate Similarity	NPD4967	Phase 2
0.8251	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.8246	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8246	Intermediate Similarity	NPD8455	Phase 2
0.8192	Intermediate Similarity	NPD7473	Discontinued
0.8182	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.8171	Intermediate Similarity	NPD6959	Discontinued
0.8167	Intermediate Similarity	NPD7240	Approved
0.8162	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.8114	Intermediate Similarity	NPD5494	Approved
0.8107	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.8103	Intermediate Similarity	NPD3749	Approved
0.8093	Intermediate Similarity	NPD8151	Discontinued
0.8087	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.8081	Intermediate Similarity	NPD1934	Approved
0.807	Intermediate Similarity	NPD4380	Phase 2
0.8059	Intermediate Similarity	NPD1653	Approved
0.8035	Intermediate Similarity	NPD7819	Suspended
0.801	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.801	Intermediate Similarity	NPD7783	Phase 2
0.8	Intermediate Similarity	NPD7075	Discontinued
0.7967	Intermediate Similarity	NPD7685	Pre-registration
0.7944	Intermediate Similarity	NPD3751	Discontinued
0.7943	Intermediate Similarity	NPD3882	Suspended
0.7933	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7919	Intermediate Similarity	NPD7411	Suspended
0.7835	Intermediate Similarity	NPD7680	Approved
0.7829	Intermediate Similarity	NPD2801	Approved
0.7829	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7824	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7821	Intermediate Similarity	NPD3787	Discontinued
0.7812	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7803	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7784	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7784	Intermediate Similarity	NPD3817	Phase 2
0.7771	Intermediate Similarity	NPD6801	Discontinued
0.7751	Intermediate Similarity	NPD3750	Approved
0.7744	Intermediate Similarity	NPD7435	Discontinued
0.774	Intermediate Similarity	NPD7768	Phase 2
0.7719	Intermediate Similarity	NPD1511	Approved
0.7684	Intermediate Similarity	NPD5402	Approved
0.768	Intermediate Similarity	NPD6782	Approved
0.768	Intermediate Similarity	NPD6777	Approved
0.768	Intermediate Similarity	NPD6776	Approved
0.768	Intermediate Similarity	NPD6778	Approved
0.768	Intermediate Similarity	NPD6781	Approved
0.768	Intermediate Similarity	NPD6780	Approved
0.768	Intermediate Similarity	NPD6779	Approved
0.7679	Intermediate Similarity	NPD7266	Discontinued
0.7674	Intermediate Similarity	NPD2533	Approved
0.7674	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7674	Intermediate Similarity	NPD2534	Approved
0.7674	Intermediate Similarity	NPD2532	Approved
0.763	Intermediate Similarity	NPD1512	Approved
0.7624	Intermediate Similarity	NPD7229	Phase 3
0.7602	Intermediate Similarity	NPD6190	Approved
0.7588	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7572	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7563	Intermediate Similarity	NPD7698	Approved
0.7563	Intermediate Similarity	NPD7696	Phase 3
0.7563	Intermediate Similarity	NPD7697	Approved
0.7556	Intermediate Similarity	NPD919	Approved
0.7544	Intermediate Similarity	NPD4628	Phase 3
0.753	Intermediate Similarity	NPD1613	Approved
0.753	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7529	Intermediate Similarity	NPD1549	Phase 2
0.7525	Intermediate Similarity	NPD7870	Phase 2
0.7525	Intermediate Similarity	NPD7871	Phase 2
0.7512	Intermediate Similarity	NPD7874	Approved
0.7512	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD3226	Approved
0.75	Intermediate Similarity	NPD7458	Discontinued
0.75	Intermediate Similarity	NPD7701	Phase 2
0.7486	Intermediate Similarity	NPD5403	Approved
0.7485	Intermediate Similarity	NPD230	Phase 1
0.7471	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7471	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7471	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7456	Intermediate Similarity	NPD3748	Approved
0.7437	Intermediate Similarity	NPD8319	Approved
0.7437	Intermediate Similarity	NPD8320	Phase 1
0.7424	Intermediate Similarity	NPD6823	Phase 2
0.7423	Intermediate Similarity	NPD6535	Approved
0.7423	Intermediate Similarity	NPD6534	Approved
0.7414	Intermediate Similarity	NPD6799	Approved
0.7413	Intermediate Similarity	NPD7585	Approved
0.7398	Intermediate Similarity	NPD7700	Phase 2
0.7398	Intermediate Similarity	NPD7699	Phase 2
0.7391	Intermediate Similarity	NPD3926	Phase 2
0.7386	Intermediate Similarity	NPD920	Approved
0.7384	Intermediate Similarity	NPD6674	Discontinued
0.7382	Intermediate Similarity	NPD8150	Discontinued
0.7377	Intermediate Similarity	NPD8127	Discontinued
0.7371	Intermediate Similarity	NPD5401	Approved
0.7371	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7363	Intermediate Similarity	NPD7583	Approved
0.736	Intermediate Similarity	NPD6599	Discontinued
0.7333	Intermediate Similarity	NPD5619	Clinical (unspecified phase)
0.733	Intermediate Similarity	NPD6273	Approved
0.7326	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7305	Intermediate Similarity	NPD3764	Approved
0.7304	Intermediate Similarity	NPD7801	Approved
0.7292	Intermediate Similarity	NPD8434	Phase 2
0.7289	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7283	Intermediate Similarity	NPD1247	Approved
0.7257	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7251	Intermediate Similarity	NPD1510	Phase 2
0.7243	Intermediate Similarity	NPD5711	Approved
0.7243	Intermediate Similarity	NPD5710	Approved
0.7241	Intermediate Similarity	NPD7003	Approved
0.7238	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.7229	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7216	Intermediate Similarity	NPD7390	Discontinued
0.7216	Intermediate Similarity	NPD4287	Approved
0.7209	Intermediate Similarity	NPD2796	Approved
0.7209	Intermediate Similarity	NPD2935	Discontinued
0.7202	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7202	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7198	Intermediate Similarity	NPD7930	Approved
0.7194	Intermediate Similarity	NPD6213	Phase 3
0.7194	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.7194	Intermediate Similarity	NPD6212	Phase 3
0.7192	Intermediate Similarity	NPD7584	Approved
0.7184	Intermediate Similarity	NPD1243	Approved
0.7181	Intermediate Similarity	NPD7177	Discontinued
0.7175	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7172	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7168	Intermediate Similarity	NPD2346	Discontinued
0.715	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD3027	Phase 3
0.7143	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7118	Intermediate Similarity	NPD943	Approved
0.711	Intermediate Similarity	NPD5405	Approved
0.711	Intermediate Similarity	NPD5406	Approved
0.711	Intermediate Similarity	NPD5408	Approved
0.711	Intermediate Similarity	NPD1551	Phase 2
0.711	Intermediate Similarity	NPD5404	Approved
0.7086	Intermediate Similarity	NPD2800	Approved
0.7083	Intermediate Similarity	NPD4908	Phase 1
0.7083	Intermediate Similarity	NPD7549	Discontinued
0.7076	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7076	Intermediate Similarity	NPD447	Suspended
0.7076	Intermediate Similarity	NPD5124	Phase 1
0.7076	Intermediate Similarity	NPD1933	Approved
0.7069	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7068	Intermediate Similarity	NPD5953	Discontinued
0.7059	Intermediate Similarity	NPD7999	Approved
0.7033	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD5242	Approved
0.7018	Intermediate Similarity	NPD1240	Approved
0.7018	Intermediate Similarity	NPD4060	Phase 1
0.7011	Intermediate Similarity	NPD4288	Approved
0.7	Intermediate Similarity	NPD6798	Discontinued
0.6995	Remote Similarity	NPD5006	Approved
0.6995	Remote Similarity	NPD5005	Approved
0.6994	Remote Similarity	NPD7097	Phase 1
0.6971	Remote Similarity	NPD2344	Approved
0.6963	Remote Similarity	NPD7286	Phase 2
0.6954	Remote Similarity	NPD651	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD2799	Discontinued
0.6954	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.6949	Remote Similarity	NPD8166	Discontinued
0.6943	Remote Similarity	NPD7038	Approved
0.6943	Remote Similarity	NPD7039	Approved
0.6941	Remote Similarity	NPD4625	Phase 3
0.6936	Remote Similarity	NPD1607	Approved
0.6928	Remote Similarity	NPD9269	Phase 2
0.6919	Remote Similarity	NPD5353	Approved
0.6914	Remote Similarity	NPD6100	Approved
0.6914	Remote Similarity	NPD6099	Approved
0.6912	Remote Similarity	NPD8059	Phase 3

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