NPASS Compound

Structure

NPC476373 OpenBabel07101718192D 47 50 0 0 1 0 0 0 0 0999 V2000 6.9282 -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 0 0 0 0 0 0 0 0 0 0 -1.7321 2.0000 0.0000 C 0 0 0 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 -2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.6603 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -3.0000 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 -4.3301 -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 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 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 -1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -3.0000 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 -8.6603 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -4.0000 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 0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.5263 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -4.5000 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 2.5981 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -2.5000 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 6.0622 -1.5000 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 -0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -1.0000 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 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 42 1 0 0 0 0 2 43 1 0 0 0 0 3 44 1 0 0 0 0 4 5 2 0 0 0 0 4 16 1 0 0 0 0 5 21 1 0 0 0 0 6 11 1 0 0 0 0 6 22 2 0 0 0 0 7 12 2 0 0 0 0 7 22 1 0 0 0 0 8 13 1 0 0 0 0 8 23 2 0 0 0 0 9 14 2 0 0 0 0 9 23 1 0 0 0 0 10 15 2 0 0 0 0 10 24 1 0 0 0 0 11 25 2 0 0 0 0 12 25 1 0 0 0 0 13 26 2 0 0 0 0 14 26 1 0 0 0 0 15 28 1 0 0 0 0 16 45 1 0 0 0 0 17 21 2 0 0 0 0 17 29 1 0 0 0 0 18 21 1 0 0 0 0 18 30 2 0 0 0 0 19 24 2 0 0 0 0 19 27 1 0 0 0 0 20 46 1 0 0 0 0 22 34 1 0 0 0 0 23 35 1 0 0 0 0 24 32 1 0 0 0 0 25 36 1 0 0 0 0 26 37 1 0 0 0 0 27 28 2 0 0 0 0 27 38 1 0 0 0 0 28 42 1 0 0 0 0 29 33 2 0 0 0 0 29 43 1 0 0 0 0 30 33 1 0 0 0 0 30 44 1 0 0 0 0 31 20 1 6 0 0 0 31 32 1 0 0 0 0 31 47 1 0 0 0 0 32 39 1 1 0 0 0 33 47 1 0 0 0 0 34 40 2 0 0 0 0 34 45 1 0 0 0 0 35 41 2 0 0 0 0 35 46 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	646.21
Volume:	645.626
LogP:	4.111
LogD:	3.383
LogS:	-3.288
# Rotatable Bonds:	16
TPSA:	170.44
# H-Bond Aceptor:	12
# H-Bond Donor:	4
# Rings:	4
# Heavy Atoms:	12

MedChem Properties

QED Drug-Likeness Score:	0.135
Synthetic Accessibility Score:	3.633
Fsp3:	0.2
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.923
MDCK Permeability:	4.0807295590639114e-05
Pgp-inhibitor:	0.525
Pgp-substrate:	0.02
Human Intestinal Absorption (HIA):	0.017
20% Bioavailability (F20%):	0.017
30% Bioavailability (F30%):	0.553

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.164
Plasma Protein Binding (PPB):	99.38504791259766%
Volume Distribution (VD):	0.357
Pgp-substrate:	4.509620189666748%

ADMET: Metabolism

CYP1A2-inhibitor:	0.383
CYP1A2-substrate:	0.758
CYP2C19-inhibitor:	0.933
CYP2C19-substrate:	0.058
CYP2C9-inhibitor:	0.877
CYP2C9-substrate:	0.974
CYP2D6-inhibitor:	0.811
CYP2D6-substrate:	0.867
CYP3A4-inhibitor:	0.899
CYP3A4-substrate:	0.51

ADMET: Excretion

Clearance (CL):	10.815
Half-life (T1/2):	0.934

ADMET: Toxicity

hERG Blockers:	0.374
Human Hepatotoxicity (H-HT):	0.014
Drug-inuced Liver Injury (DILI):	0.756
AMES Toxicity:	0.014
Rat Oral Acute Toxicity:	0.011
Maximum Recommended Daily Dose:	0.028
Skin Sensitization:	0.787
Carcinogencity:	0.444
Eye Corrosion:	0.003
Eye Irritation:	0.613
Respiratory Toxicity:	0.009

Download Data

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

Natural Product: NPC476373

Natural Product ID:	NPC476373
*Common Name:**	Quiquelignan H
IUPAC Name:	[(E)-3-[4-[(1S,2S)-1-hydroxy-3-(4-hydroxybenzoyl)oxy-1-(3-hydroxy-4-methoxyphenyl)propan-2-yl]oxy-3,5-dimethoxyphenyl]prop-2-enyl] 4-hydroxybenzoate
Synonyms:	Quiquelignan H
Standard InCHIKey:	TXFCLWBWJFJPIC-QFEFOYBJSA-N
Standard InCHI:	InChI=1S/C35H34O12/c1-42-28-15-10-24(19-27(28)38)32(39)31(20-46-35(41)23-8-13-26(37)14-9-23)47-33-29(43-2)17-21(18-30(33)44-3)5-4-16-45-34(40)22-6-11-25(36)12-7-22/h4-15,17-19,31-32,36-39H,16,20H2,1-3H3/b5-4+/t31-,32-/m0/s1
SMILES:	COc1cc(/C=C/COC(=O)c2ccc(cc2)O)cc(c1O[C@H]([C@H](c1ccc(c(c1)O)OC)O)COC(=O)c1ccc(cc1)O)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL590185
PubChem CID:	46232302
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0001392] Lignans, neolignans and related compounds

*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
NPO32697	calamus quiquesetinervius	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[20056545]
NPO32697	calamus quiquesetinervius	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[20825224]

☑ 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	4
Others	2

Activity Type	# Activity
Cell Line	3
NON-MOLECULAR	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	52400.0	nM	PMID[504450]
NPT113	Cell Line	RAW264.7	Mus musculus	Activity	>	85.0	%	PMID[504450]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	20400.0	nM	PMID[504450]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	55200.0	nM	PMID[504450]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	200000.0	nM	PMID[504450]

☑ 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 NPC476373 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	361
0.1-0.2	1512
0.2-0.3	3787
0.3-0.4	9097
0.4-0.5	9304
0.5-0.6	3509
0.6-0.7	5135
0.7-0.8	6933
0.8-0.85	2412
0.85-0.9	570
0.9-0.95	73
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9869	High Similarity	NPC476371
0.9869	High Similarity	NPC476372
0.9669	High Similarity	NPC469888
0.9408	High Similarity	NPC75695
0.9379	High Similarity	NPC476374
0.9375	High Similarity	NPC476365
0.9375	High Similarity	NPC180768
0.9359	High Similarity	NPC53889
0.9338	High Similarity	NPC475250
0.9317	High Similarity	NPC476370
0.9295	High Similarity	NPC87317
0.9276	High Similarity	NPC473091
0.9241	High Similarity	NPC33298
0.9241	High Similarity	NPC285108
0.9236	High Similarity	NPC24164
0.9231	High Similarity	NPC156818
0.9231	High Similarity	NPC68324
0.9231	High Similarity	NPC289322
0.9231	High Similarity	NPC38779
0.9231	High Similarity	NPC160512
0.9231	High Similarity	NPC114179
0.9193	High Similarity	NPC197708
0.9193	High Similarity	NPC658
0.9167	High Similarity	NPC104983
0.9167	High Similarity	NPC250436
0.9167	High Similarity	NPC291948
0.9167	High Similarity	NPC88803
0.9167	High Similarity	NPC300845
0.9152	High Similarity	NPC471030
0.9145	High Similarity	NPC472969
0.913	High Similarity	NPC473818
0.9125	High Similarity	NPC142614
0.9114	High Similarity	NPC289346
0.9114	High Similarity	NPC203020
0.9114	High Similarity	NPC239966
0.9103	High Similarity	NPC145425
0.9097	High Similarity	NPC474656
0.9085	High Similarity	NPC476394
0.9085	High Similarity	NPC98809
0.908	High Similarity	NPC5786
0.908	High Similarity	NPC102851
0.9074	High Similarity	NPC149300
0.9074	High Similarity	NPC95421
0.9074	High Similarity	NPC198125
0.9073	High Similarity	NPC473909
0.9073	High Similarity	NPC274960
0.9073	High Similarity	NPC143120
0.9062	High Similarity	NPC45943
0.9057	High Similarity	NPC158188
0.9051	High Similarity	NPC289811
0.9051	High Similarity	NPC172202
0.9051	High Similarity	NPC160780
0.9051	High Similarity	NPC476410
0.9051	High Similarity	NPC284127
0.9045	High Similarity	NPC470896
0.9045	High Similarity	NPC473275
0.9045	High Similarity	NPC318432
0.903	High Similarity	NPC79736
0.903	High Similarity	NPC67629
0.9024	High Similarity	NPC172033
0.9024	High Similarity	NPC98583
0.9024	High Similarity	NPC88560
0.9024	High Similarity	NPC175230
0.9006	High Similarity	NPC477840
0.9	High Similarity	NPC4013
0.9	High Similarity	NPC90905
0.8987	High Similarity	NPC63454
0.8987	High Similarity	NPC133984
0.8987	High Similarity	NPC472860
0.8987	High Similarity	NPC1913
0.8987	High Similarity	NPC183851
0.8982	High Similarity	NPC117668
0.8976	High Similarity	NPC267549
0.8974	High Similarity	NPC146277
0.8974	High Similarity	NPC19380
0.8968	High Similarity	NPC243891
0.8963	High Similarity	NPC100251
0.8963	High Similarity	NPC65333
0.8957	High Similarity	NPC476279
0.8957	High Similarity	NPC475212
0.8938	High Similarity	NPC113163
0.8938	High Similarity	NPC311803
0.8938	High Similarity	NPC84324
0.8938	High Similarity	NPC216916
0.8938	High Similarity	NPC66618
0.8938	High Similarity	NPC288131
0.8938	High Similarity	NPC165970
0.8938	High Similarity	NPC472859
0.8938	High Similarity	NPC305987
0.8938	High Similarity	NPC25389
0.8935	High Similarity	NPC474093
0.8935	High Similarity	NPC104910
0.891	High Similarity	NPC93498
0.891	High Similarity	NPC267091
0.891	High Similarity	NPC163883
0.8909	High Similarity	NPC472993
0.8902	High Similarity	NPC149011
0.8902	High Similarity	NPC204937
0.8896	High Similarity	NPC142528
0.8889	High Similarity	NPC471788
0.8882	High Similarity	NPC477841
0.8882	High Similarity	NPC475179
0.8882	High Similarity	NPC476247
0.8882	High Similarity	NPC473090
0.8882	High Similarity	NPC148273
0.8882	High Similarity	NPC473445
0.8882	High Similarity	NPC219927
0.8875	High Similarity	NPC101731
0.8875	High Similarity	NPC188967
0.8875	High Similarity	NPC24627
0.8875	High Similarity	NPC166277
0.8875	High Similarity	NPC119125
0.8861	High Similarity	NPC222185
0.8839	High Similarity	NPC107636
0.8834	High Similarity	NPC43065
0.8834	High Similarity	NPC471823
0.8827	High Similarity	NPC291977
0.8827	High Similarity	NPC121290
0.882	High Similarity	NPC142252
0.8817	High Similarity	NPC35924
0.8817	High Similarity	NPC199172
0.8812	High Similarity	NPC154304
0.8812	High Similarity	NPC190487
0.8812	High Similarity	NPC74319
0.8812	High Similarity	NPC287872
0.881	High Similarity	NPC80956
0.8805	High Similarity	NPC247629
0.8805	High Similarity	NPC239019
0.8805	High Similarity	NPC471405
0.8805	High Similarity	NPC165483
0.8802	High Similarity	NPC472723
0.8797	High Similarity	NPC191046
0.8797	High Similarity	NPC194095
0.8797	High Similarity	NPC327032
0.879	High Similarity	NPC476434
0.8782	High Similarity	NPC306343
0.878	High Similarity	NPC243877
0.878	High Similarity	NPC14662
0.878	High Similarity	NPC116745
0.8773	High Similarity	NPC72787
0.8773	High Similarity	NPC36
0.8773	High Similarity	NPC125039
0.8773	High Similarity	NPC36916
0.8773	High Similarity	NPC7688
0.8773	High Similarity	NPC58223
0.8773	High Similarity	NPC7154
0.8772	High Similarity	NPC30011
0.8772	High Similarity	NPC97817
0.8772	High Similarity	NPC72554
0.8766	High Similarity	NPC9370
0.8766	High Similarity	NPC287495
0.8765	High Similarity	NPC470717
0.8765	High Similarity	NPC25946
0.8765	High Similarity	NPC470720
0.8765	High Similarity	NPC249070
0.8765	High Similarity	NPC470713
0.8765	High Similarity	NPC460984
0.8765	High Similarity	NPC42797
0.8765	High Similarity	NPC21359
0.8758	High Similarity	NPC121573
0.8758	High Similarity	NPC226738
0.8758	High Similarity	NPC190587
0.8758	High Similarity	NPC134975
0.8758	High Similarity	NPC22176
0.875	High Similarity	NPC183
0.875	High Similarity	NPC139571
0.875	High Similarity	NPC112954
0.875	High Similarity	NPC185526
0.875	High Similarity	NPC222689
0.875	High Similarity	NPC172419
0.875	High Similarity	NPC35598
0.875	High Similarity	NPC217520
0.875	High Similarity	NPC477895
0.875	High Similarity	NPC238419
0.875	High Similarity	NPC125495
0.8742	High Similarity	NPC203757
0.8742	High Similarity	NPC10205
0.8735	High Similarity	NPC47140
0.8735	High Similarity	NPC67134
0.8735	High Similarity	NPC271848
0.8735	High Similarity	NPC81332
0.8735	High Similarity	NPC262580
0.8735	High Similarity	NPC289396
0.8735	High Similarity	NPC212038
0.8734	High Similarity	NPC105827
0.8734	High Similarity	NPC157898
0.8734	High Similarity	NPC310661
0.8734	High Similarity	NPC289968
0.8727	High Similarity	NPC280493
0.8726	High Similarity	NPC252979
0.8726	High Similarity	NPC300329
0.872	High Similarity	NPC9309
0.872	High Similarity	NPC207575
0.872	High Similarity	NPC13481
0.8718	High Similarity	NPC42464
0.8713	High Similarity	NPC470719
0.8713	High Similarity	NPC295625
0.8713	High Similarity	NPC473554
0.8712	High Similarity	NPC100425
0.8712	High Similarity	NPC272064

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 NPC476373 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	309
0.1-0.2	896
0.2-0.3	1742
0.3-0.4	2601
0.4-0.5	1864
0.5-0.6	1034
0.6-0.7	535
0.7-0.8	123
0.8-0.85	38
0.85-0.9	7
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9167	High Similarity	NPD4868	Clinical (unspecified phase)
0.8963	High Similarity	NPD7993	Clinical (unspecified phase)
0.8773	High Similarity	NPD6168	Clinical (unspecified phase)
0.8773	High Similarity	NPD6167	Clinical (unspecified phase)
0.8773	High Similarity	NPD6166	Phase 2
0.8616	High Similarity	NPD1934	Approved
0.8614	High Similarity	NPD7054	Approved
0.8614	High Similarity	NPD5844	Phase 1
0.8563	High Similarity	NPD7074	Phase 3
0.8563	High Similarity	NPD7472	Approved
0.8509	High Similarity	NPD3817	Phase 2
0.8447	Intermediate Similarity	NPD2801	Approved
0.8447	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8443	Intermediate Similarity	NPD3818	Discontinued
0.8412	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8412	Intermediate Similarity	NPD7808	Phase 3
0.8353	Intermediate Similarity	NPD7251	Discontinued
0.8344	Intermediate Similarity	NPD3882	Suspended
0.8333	Intermediate Similarity	NPD1465	Phase 2
0.8302	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.8294	Intermediate Similarity	NPD6797	Phase 2
0.8293	Intermediate Similarity	NPD7075	Discontinued
0.8232	Intermediate Similarity	NPD7768	Phase 2
0.8228	Intermediate Similarity	NPD1511	Approved
0.8224	Intermediate Similarity	NPD230	Phase 1
0.8217	Intermediate Similarity	NPD6190	Approved
0.8204	Intermediate Similarity	NPD6232	Discontinued
0.8182	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8166	Intermediate Similarity	NPD7473	Discontinued
0.8153	Intermediate Similarity	NPD4628	Phase 3
0.8148	Intermediate Similarity	NPD4380	Phase 2
0.814	Intermediate Similarity	NPD7685	Pre-registration
0.8125	Intermediate Similarity	NPD1512	Approved
0.811	Intermediate Similarity	NPD7819	Suspended
0.811	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8107	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8098	Intermediate Similarity	NPD7411	Suspended
0.8061	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8061	Intermediate Similarity	NPD5402	Approved
0.8049	Intermediate Similarity	NPD6801	Discontinued
0.8036	Intermediate Similarity	NPD7199	Phase 2
0.8023	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD6799	Approved
0.7965	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7963	Intermediate Similarity	NPD5403	Approved
0.7961	Intermediate Similarity	NPD3027	Phase 3
0.7955	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7929	Intermediate Similarity	NPD6959	Discontinued
0.7917	Intermediate Similarity	NPD6234	Discontinued
0.7914	Intermediate Similarity	NPD1653	Approved
0.7908	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7907	Intermediate Similarity	NPD7228	Approved
0.787	Intermediate Similarity	NPD5494	Approved
0.7862	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7848	Intermediate Similarity	NPD7266	Discontinued
0.784	Intermediate Similarity	NPD5401	Approved
0.784	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7836	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7831	Intermediate Similarity	NPD37	Approved
0.7829	Intermediate Similarity	NPD6559	Discontinued
0.7824	Intermediate Similarity	NPD8127	Discontinued
0.7812	Intermediate Similarity	NPD3750	Approved
0.7806	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7806	Intermediate Similarity	NPD1613	Approved
0.7799	Intermediate Similarity	NPD1549	Phase 2
0.7798	Intermediate Similarity	NPD4966	Approved
0.7798	Intermediate Similarity	NPD4965	Approved
0.7798	Intermediate Similarity	NPD4967	Phase 2
0.7784	Intermediate Similarity	NPD8455	Phase 2
0.774	Intermediate Similarity	NPD8313	Approved
0.774	Intermediate Similarity	NPD8312	Approved
0.7736	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7736	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.773	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7711	Intermediate Similarity	NPD6599	Discontinued
0.7673	Intermediate Similarity	NPD2796	Approved
0.7647	Intermediate Similarity	NPD3749	Approved
0.7637	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7633	Intermediate Similarity	NPD5353	Approved
0.7628	Intermediate Similarity	NPD6233	Phase 2
0.7627	Intermediate Similarity	NPD7039	Approved
0.7627	Intermediate Similarity	NPD7038	Approved
0.7622	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.761	Intermediate Similarity	NPD1510	Phase 2
0.7597	Intermediate Similarity	NPD9494	Approved
0.7578	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7568	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7562	Intermediate Similarity	NPD1551	Phase 2
0.756	Intermediate Similarity	NPD6385	Approved
0.756	Intermediate Similarity	NPD6386	Approved
0.7548	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7532	Intermediate Similarity	NPD447	Suspended
0.7529	Intermediate Similarity	NPD5242	Approved
0.75	Intermediate Similarity	NPD3748	Approved
0.75	Intermediate Similarity	NPD919	Approved
0.75	Intermediate Similarity	NPD9269	Phase 2
0.7485	Intermediate Similarity	NPD8166	Discontinued
0.7484	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.747	Intermediate Similarity	NPD6273	Approved
0.7468	Intermediate Similarity	NPD1240	Approved
0.7453	Intermediate Similarity	NPD2935	Discontinued
0.7452	Intermediate Similarity	NPD6798	Discontinued
0.7451	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.744	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.743	Intermediate Similarity	NPD7240	Approved
0.7429	Intermediate Similarity	NPD3926	Phase 2
0.7418	Intermediate Similarity	NPD8434	Phase 2
0.7409	Intermediate Similarity	NPD8151	Discontinued
0.7401	Intermediate Similarity	NPD3751	Discontinued
0.7378	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7375	Intermediate Similarity	NPD1607	Approved
0.7371	Intermediate Similarity	NPD3787	Discontinued
0.7358	Intermediate Similarity	NPD943	Approved
0.7341	Intermediate Similarity	NPD6971	Discontinued
0.7337	Intermediate Similarity	NPD7458	Discontinued
0.7325	Intermediate Similarity	NPD6832	Phase 2
0.7325	Intermediate Similarity	NPD4908	Phase 1
0.7312	Intermediate Similarity	NPD1933	Approved
0.7305	Intermediate Similarity	NPD2532	Approved
0.7305	Intermediate Similarity	NPD2534	Approved
0.7305	Intermediate Similarity	NPD2533	Approved
0.7289	Intermediate Similarity	NPD7440	Discontinued
0.7285	Intermediate Similarity	NPD9545	Approved
0.7273	Intermediate Similarity	NPD1608	Approved
0.7273	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD7229	Phase 3
0.724	Intermediate Similarity	NPD7680	Approved
0.7237	Intermediate Similarity	NPD9268	Approved
0.7235	Intermediate Similarity	NPD3455	Phase 2
0.7235	Intermediate Similarity	NPD3226	Approved
0.7233	Intermediate Similarity	NPD3764	Approved
0.7233	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7228	Intermediate Similarity	NPD8150	Discontinued
0.7216	Intermediate Similarity	NPD1247	Approved
0.7212	Intermediate Similarity	NPD1652	Phase 2
0.7207	Intermediate Similarity	NPD7177	Discontinued
0.7205	Intermediate Similarity	NPD6355	Discontinued
0.7198	Intermediate Similarity	NPD7549	Discontinued
0.7182	Intermediate Similarity	NPD5953	Discontinued
0.7178	Intermediate Similarity	NPD7033	Discontinued
0.717	Intermediate Similarity	NPD7095	Approved
0.7169	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7169	Intermediate Similarity	NPD4110	Phase 3
0.7167	Intermediate Similarity	NPD7286	Phase 2
0.7157	Intermediate Similarity	NPD7783	Phase 2
0.7157	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.715	Intermediate Similarity	NPD7435	Discontinued
0.7143	Intermediate Similarity	NPD7390	Discontinued
0.7134	Intermediate Similarity	NPD1203	Approved
0.7134	Intermediate Similarity	NPD6099	Approved
0.7134	Intermediate Similarity	NPD6100	Approved
0.712	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.712	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7118	Intermediate Similarity	NPD920	Approved
0.7117	Intermediate Similarity	NPD7097	Phase 1
0.7101	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD5124	Phase 1
0.7099	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD422	Phase 1
0.7095	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7092	Intermediate Similarity	NPD7585	Approved
0.7083	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD4062	Phase 3
0.7078	Intermediate Similarity	NPD17	Approved
0.7073	Intermediate Similarity	NPD4308	Phase 3
0.707	Intermediate Similarity	NPD3225	Approved
0.7066	Intermediate Similarity	NPD7003	Approved
0.7055	Intermediate Similarity	NPD6653	Approved
0.7041	Intermediate Similarity	NPD4357	Discontinued
0.7041	Intermediate Similarity	NPD7583	Approved
0.703	Intermediate Similarity	NPD5405	Approved
0.703	Intermediate Similarity	NPD5404	Approved
0.703	Intermediate Similarity	NPD5406	Approved
0.703	Intermediate Similarity	NPD5408	Approved
0.7029	Intermediate Similarity	NPD4288	Approved
0.7026	Intermediate Similarity	NPD7871	Phase 2
0.7026	Intermediate Similarity	NPD7870	Phase 2
0.7025	Intermediate Similarity	NPD2797	Approved
0.7024	Intermediate Similarity	NPD2354	Approved
0.7024	Intermediate Similarity	NPD3887	Approved
0.702	Intermediate Similarity	NPD7874	Approved
0.702	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD3268	Approved
0.7006	Intermediate Similarity	NPD2982	Phase 2
0.7006	Intermediate Similarity	NPD1243	Approved
0.7006	Intermediate Similarity	NPD2983	Phase 2
0.7	Intermediate Similarity	NPD3146	Approved
0.7	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD3688	Clinical (unspecified phase)
0.6995	Remote Similarity	NPD6780	Approved
0.6995	Remote Similarity	NPD6777	Approved
0.6995	Remote Similarity	NPD6778	Approved
0.6995	Remote Similarity	NPD6779	Approved
0.6995	Remote Similarity	NPD6782	Approved
0.6995	Remote Similarity	NPD6781	Approved
0.6995	Remote Similarity	NPD6776	Approved
0.6993	Remote Similarity	NPD5536	Phase 2

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