NPASS Compound

Structure

NPC158188 OpenBabel07101718242D 40 43 0 0 1 0 0 0 0 0999 V2000 -0.8660 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 -0.0000 2.0000 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 -4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 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 5.1962 -4.0000 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 3.4641 -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 -3.4641 0.0000 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 4.3301 -4.5000 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 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 2.5981 -1.5000 0.0000 C 0 0 1 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 3.4641 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 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 -1.7321 0.0000 0.0000 C 0 0 1 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 -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 -2.5981 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -5.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -2.5000 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 -6.0622 0.5000 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 -2.5981 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -2.5000 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 5 1 0 0 0 0 2 35 1 0 0 0 0 3 36 1 0 0 0 0 4 37 1 0 0 0 0 5 38 1 0 0 0 0 6 7 2 0 0 0 0 6 15 1 0 0 0 0 7 18 1 0 0 0 0 8 15 2 0 0 0 0 8 22 1 0 0 0 0 9 16 2 0 0 0 0 9 24 1 0 0 0 0 10 16 1 0 0 0 0 10 25 2 0 0 0 0 11 17 2 0 0 0 0 11 19 1 0 0 0 0 12 17 1 0 0 0 0 12 23 2 0 0 0 0 13 20 1 0 0 0 0 13 21 1 0 0 0 0 14 30 1 0 0 0 0 15 28 1 0 0 0 0 17 31 1 0 0 0 0 18 22 2 0 0 0 0 18 32 1 0 0 0 0 19 27 2 0 0 0 0 19 33 1 0 0 0 0 20 27 1 0 0 0 0 20 34 2 0 0 0 0 21 16 1 6 0 0 0 21 39 1 0 0 0 0 22 35 1 0 0 0 0 23 27 1 0 0 0 0 23 39 1 0 0 0 0 24 29 2 0 0 0 0 24 36 1 0 0 0 0 25 29 1 0 0 0 0 25 37 1 0 0 0 0 26 14 1 1 0 0 0 26 28 1 0 0 0 0 26 40 1 0 0 0 0 28 38 1 6 0 0 0 29 40 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	556.19
Volume:	546.242
LogP:	3.168
LogD:	2.942
LogS:	-4.713
# Rotatable Bonds:	11
TPSA:	153.37
# H-Bond Aceptor:	11
# H-Bond Donor:	4
# Rings:	4
# Heavy Atoms:	11

MedChem Properties

QED Drug-Likeness Score:	0.27
Synthetic Accessibility Score:	3.987
Fsp3:	0.345
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.944
MDCK Permeability:	3.510162059683353e-05
Pgp-inhibitor:	0.359
Pgp-substrate:	0.291
Human Intestinal Absorption (HIA):	0.024
20% Bioavailability (F20%):	0.001
30% Bioavailability (F30%):	0.08

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.028
Plasma Protein Binding (PPB):	80.52213287353516%
Volume Distribution (VD):	0.619
Pgp-substrate:	24.860334396362305%

ADMET: Metabolism

CYP1A2-inhibitor:	0.027
CYP1A2-substrate:	0.354
CYP2C19-inhibitor:	0.196
CYP2C19-substrate:	0.171
CYP2C9-inhibitor:	0.721
CYP2C9-substrate:	0.792
CYP2D6-inhibitor:	0.229
CYP2D6-substrate:	0.438
CYP3A4-inhibitor:	0.84
CYP3A4-substrate:	0.631

ADMET: Excretion

Clearance (CL):	13.058
Half-life (T1/2):	0.631

ADMET: Toxicity

hERG Blockers:	0.187
Human Hepatotoxicity (H-HT):	0.354
Drug-inuced Liver Injury (DILI):	0.934
AMES Toxicity:	0.055
Rat Oral Acute Toxicity:	0.61
Maximum Recommended Daily Dose:	0.792
Skin Sensitization:	0.923
Carcinogencity:	0.088
Eye Corrosion:	0.003
Eye Irritation:	0.436
Respiratory Toxicity:	0.613

Download Data

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

Natural Product: NPC158188

Natural Product ID:	NPC158188
*Common Name:**	Quiquelignan A
IUPAC Name:	(2S)-2-[4-[(1S,2S)-1-ethoxy-3-hydroxy-1-(4-hydroxy-3-methoxyphenyl)propan-2-yl]oxy-3,5-dimethoxyphenyl]-5,7-dihydroxy-2,3-dihydrochromen-4-one
Synonyms:
Standard InCHIKey:	FEQZBFHFXKCFBZ-PTJQVGQKSA-N
Standard InCHI:	InChI=1S/C29H32O11/c1-5-38-28(15-6-7-18(32)22(8-15)35-2)26(14-30)40-29-24(36-3)9-16(10-25(29)37-4)21-13-20(34)27-19(33)11-17(31)12-23(27)39-21/h6-12,21,26,28,30-33H,5,13-14H2,1-4H3/t21-,26-,28-/m0/s1
SMILES:	CCO[C@@H](c1ccc(c(c1)OC)O)[C@@H](Oc1c(OC)cc(cc1OC)[C@@H]1CC(=O)c2c(O1)cc(cc2O)O)CO
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL598315
PubChem CID:	46232229
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0002585] O-methylated flavonoids [CHEMONTID:0002595] 3'-O-methylated 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
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	3

Activity Type	# Activity
NON-MOLECULAR	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	27400.0	nM	PMID[488803]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	100000.0	nM	PMID[488803]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	200000.0	nM	PMID[488803]

☑ 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 NPC158188 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	410
0.1-0.2	1558
0.2-0.3	3855
0.3-0.4	9736
0.4-0.5	8596
0.5-0.6	3411
0.6-0.7	4725
0.7-0.8	5231
0.8-0.85	2735
0.85-0.9	2009
0.9-0.95	396
0.95-1	35

Similarity Score	Similarity Level	Natural Product ID
0.974	High Similarity	NPC66618
0.974	High Similarity	NPC113163
0.974	High Similarity	NPC305987
0.974	High Similarity	NPC84324
0.974	High Similarity	NPC288131
0.974	High Similarity	NPC142252
0.974	High Similarity	NPC165970
0.9739	High Similarity	NPC172202
0.9739	High Similarity	NPC476410
0.9739	High Similarity	NPC284127
0.9679	High Similarity	NPC58223
0.9679	High Similarity	NPC7154
0.9679	High Similarity	NPC7688
0.9679	High Similarity	NPC125039
0.9679	High Similarity	NPC72787
0.9679	High Similarity	NPC36916
0.9679	High Similarity	NPC36
0.9677	High Similarity	NPC476247
0.9675	High Similarity	NPC101731
0.9673	High Similarity	NPC63454
0.9673	High Similarity	NPC183851
0.9613	High Similarity	NPC472634
0.9613	High Similarity	NPC26326
0.9605	High Similarity	NPC18727
0.9557	High Similarity	NPC243877
0.9557	High Similarity	NPC14662
0.9554	High Similarity	NPC477840
0.9551	High Similarity	NPC477841
0.9551	High Similarity	NPC219927
0.9548	High Similarity	NPC472630
0.9548	High Similarity	NPC472631
0.9545	High Similarity	NPC474055
0.9545	High Similarity	NPC472598
0.9539	High Similarity	NPC236637
0.9539	High Similarity	NPC219582
0.9539	High Similarity	NPC302950
0.9497	High Similarity	NPC475212
0.9494	High Similarity	NPC471213
0.9487	High Similarity	NPC471499
0.9487	High Similarity	NPC471210
0.9487	High Similarity	NPC471211
0.9487	High Similarity	NPC474038
0.9487	High Similarity	NPC472632
0.9487	High Similarity	NPC471212
0.9484	High Similarity	NPC117418
0.9484	High Similarity	NPC53545
0.9481	High Similarity	NPC470328
0.9481	High Similarity	NPC291878
0.9481	High Similarity	NPC195796
0.9481	High Similarity	NPC250922
0.9481	High Similarity	NPC209614
0.9481	High Similarity	NPC35038
0.9481	High Similarity	NPC320825
0.9481	High Similarity	NPC278778
0.9481	High Similarity	NPC472626
0.9481	High Similarity	NPC13858
0.9481	High Similarity	NPC326037
0.9437	High Similarity	NPC102277
0.9437	High Similarity	NPC476365
0.9437	High Similarity	NPC279209
0.9434	High Similarity	NPC295082
0.9427	High Similarity	NPC474033
0.9427	High Similarity	NPC472635
0.9427	High Similarity	NPC474034
0.9427	High Similarity	NPC472964
0.9423	High Similarity	NPC470326
0.9423	High Similarity	NPC119209
0.9423	High Similarity	NPC118256
0.9423	High Similarity	NPC282009
0.9423	High Similarity	NPC287328
0.9423	High Similarity	NPC470183
0.9423	High Similarity	NPC475784
0.9423	High Similarity	NPC192686
0.9423	High Similarity	NPC174953
0.9419	High Similarity	NPC471479
0.9419	High Similarity	NPC474836
0.9419	High Similarity	NPC52530
0.9419	High Similarity	NPC471515
0.9419	High Similarity	NPC156057
0.9419	High Similarity	NPC48208
0.9419	High Similarity	NPC291508
0.9419	High Similarity	NPC474208
0.9419	High Similarity	NPC162869
0.9419	High Similarity	NPC27337
0.9419	High Similarity	NPC475267
0.9416	High Similarity	NPC321779
0.9416	High Similarity	NPC45849
0.9416	High Similarity	NPC200761
0.9416	High Similarity	NPC470327
0.9416	High Similarity	NPC477503
0.9416	High Similarity	NPC226025
0.9412	High Similarity	NPC472912
0.9408	High Similarity	NPC338131
0.9371	High Similarity	NPC236934
0.9371	High Similarity	NPC5778
0.9367	High Similarity	NPC472625
0.9363	High Similarity	NPC289771
0.9359	High Similarity	NPC473990
0.9359	High Similarity	NPC22192
0.9355	High Similarity	NPC78492
0.9355	High Similarity	NPC208152
0.9355	High Similarity	NPC471500
0.9355	High Similarity	NPC255106
0.9355	High Similarity	NPC235165
0.9351	High Similarity	NPC192083
0.9351	High Similarity	NPC298692
0.9351	High Similarity	NPC213896
0.9317	High Similarity	NPC44328
0.9317	High Similarity	NPC79056
0.9317	High Similarity	NPC177731
0.9317	High Similarity	NPC105095
0.9313	High Similarity	NPC260266
0.9313	High Similarity	NPC229729
0.9308	High Similarity	NPC311830
0.9308	High Similarity	NPC293319
0.9308	High Similarity	NPC471788
0.9308	High Similarity	NPC22832
0.9304	High Similarity	NPC201800
0.9304	High Similarity	NPC300537
0.9304	High Similarity	NPC127782
0.9299	High Similarity	NPC472624
0.9299	High Similarity	NPC472902
0.9299	High Similarity	NPC263449
0.9299	High Similarity	NPC36217
0.9299	High Similarity	NPC321399
0.9299	High Similarity	NPC53889
0.9295	High Similarity	NPC99597
0.9295	High Similarity	NPC470402
0.9295	High Similarity	NPC223787
0.9295	High Similarity	NPC299520
0.9295	High Similarity	NPC472910
0.9295	High Similarity	NPC472911
0.9295	High Similarity	NPC245758
0.9295	High Similarity	NPC471209
0.9295	High Similarity	NPC67876
0.9295	High Similarity	NPC96167
0.9295	High Similarity	NPC129684
0.9295	High Similarity	NPC284820
0.9295	High Similarity	NPC472913
0.9295	High Similarity	NPC473272
0.9295	High Similarity	NPC472914
0.9295	High Similarity	NPC222814
0.9295	High Similarity	NPC210084
0.929	High Similarity	NPC67396
0.929	High Similarity	NPC37392
0.9286	High Similarity	NPC240476
0.9286	High Similarity	NPC36835
0.9286	High Similarity	NPC260979
0.9286	High Similarity	NPC9743
0.9286	High Similarity	NPC106976
0.9286	High Similarity	NPC260491
0.9286	High Similarity	NPC19721
0.9286	High Similarity	NPC257648
0.9286	High Similarity	NPC61506
0.9286	High Similarity	NPC246162
0.9286	High Similarity	NPC477231
0.9276	High Similarity	NPC188679
0.9276	High Similarity	NPC294852
0.9276	High Similarity	NPC321011
0.9259	High Similarity	NPC261254
0.9255	High Similarity	NPC195257
0.9255	High Similarity	NPC293629
0.9255	High Similarity	NPC229687
0.9255	High Similarity	NPC209296
0.9255	High Similarity	NPC188079
0.9255	High Similarity	NPC43587
0.9245	High Similarity	NPC124038
0.9245	High Similarity	NPC29830
0.9245	High Similarity	NPC270335
0.9245	High Similarity	NPC222936
0.9245	High Similarity	NPC186686
0.9245	High Similarity	NPC284960
0.9245	High Similarity	NPC309025
0.9245	High Similarity	NPC88023
0.9245	High Similarity	NPC191306
0.9245	High Similarity	NPC19709
0.9245	High Similarity	NPC243930
0.9241	High Similarity	NPC112418
0.9241	High Similarity	NPC308992
0.9241	High Similarity	NPC134783
0.9241	High Similarity	NPC266314
0.9241	High Similarity	NPC173137
0.9236	High Similarity	NPC250214
0.9236	High Similarity	NPC95936
0.9236	High Similarity	NPC210459
0.9236	High Similarity	NPC87317
0.9231	High Similarity	NPC24640
0.9231	High Similarity	NPC472916
0.9226	High Similarity	NPC246328
0.9226	High Similarity	NPC74924
0.9226	High Similarity	NPC469550
0.9226	High Similarity	NPC325028
0.9226	High Similarity	NPC27532
0.9226	High Similarity	NPC256346
0.9221	High Similarity	NPC31363
0.9216	High Similarity	NPC177298
0.9216	High Similarity	NPC183950
0.9216	High Similarity	NPC137062
0.9216	High Similarity	NPC52005
0.9216	High Similarity	NPC223579

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 NPC158188 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	364
0.1-0.2	900
0.2-0.3	1743
0.3-0.4	2614
0.4-0.5	1825
0.5-0.6	1003
0.6-0.7	501
0.7-0.8	138
0.8-0.85	30
0.85-0.9	24
0.9-0.95	4
0.95-1	4

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9679	High Similarity	NPD6168	Clinical (unspecified phase)
0.9679	High Similarity	NPD6166	Phase 2
0.9679	High Similarity	NPD6167	Clinical (unspecified phase)
0.9539	High Similarity	NPD1934	Approved
0.9351	High Similarity	NPD2393	Clinical (unspecified phase)
0.9317	High Similarity	NPD7074	Phase 3
0.9255	High Similarity	NPD7054	Approved
0.9198	High Similarity	NPD7472	Approved
0.9108	High Similarity	NPD4868	Clinical (unspecified phase)
0.9103	High Similarity	NPD2801	Approved
0.897	High Similarity	NPD7251	Discontinued
0.8957	High Similarity	NPD3818	Discontinued
0.8916	High Similarity	NPD7808	Phase 3
0.891	High Similarity	NPD4380	Phase 2
0.8909	High Similarity	NPD6797	Phase 2
0.8889	High Similarity	NPD1511	Approved
0.8868	High Similarity	NPD3882	Suspended
0.8812	High Similarity	NPD4381	Clinical (unspecified phase)
0.8805	High Similarity	NPD8443	Clinical (unspecified phase)
0.8805	High Similarity	NPD3817	Phase 2
0.8802	High Similarity	NPD4338	Clinical (unspecified phase)
0.8774	High Similarity	NPD1512	Approved
0.8696	High Similarity	NPD7075	Discontinued
0.8683	High Similarity	NPD7993	Clinical (unspecified phase)
0.8618	High Similarity	NPD1552	Clinical (unspecified phase)
0.8618	High Similarity	NPD1550	Clinical (unspecified phase)
0.8589	High Similarity	NPD5494	Approved
0.8563	High Similarity	NPD5844	Phase 1
0.8563	High Similarity	NPD7804	Clinical (unspecified phase)
0.8562	High Similarity	NPD1549	Phase 2
0.8554	High Similarity	NPD7473	Discontinued
0.8537	High Similarity	NPD6959	Discontinued
0.8509	High Similarity	NPD7096	Clinical (unspecified phase)
0.85	High Similarity	NPD7411	Suspended
0.8485	Intermediate Similarity	NPD6232	Discontinued
0.8471	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8471	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8395	Intermediate Similarity	NPD7819	Suspended
0.8333	Intermediate Similarity	NPD6801	Discontinued
0.8312	Intermediate Similarity	NPD2796	Approved
0.8304	Intermediate Similarity	NPD6559	Discontinued
0.8282	Intermediate Similarity	NPD1465	Phase 2
0.8247	Intermediate Similarity	NPD1510	Phase 2
0.8232	Intermediate Similarity	NPD5402	Approved
0.8224	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.8224	Intermediate Similarity	NPD1613	Approved
0.8176	Intermediate Similarity	NPD6799	Approved
0.8166	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8137	Intermediate Similarity	NPD5403	Approved
0.8105	Intermediate Similarity	NPD1240	Approved
0.8072	Intermediate Similarity	NPD7768	Phase 2
0.8026	Intermediate Similarity	NPD3027	Phase 3
0.8025	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.8012	Intermediate Similarity	NPD5401	Approved
0.8	Intermediate Similarity	NPD1607	Approved
0.8	Intermediate Similarity	NPD3926	Phase 2
0.7988	Intermediate Similarity	NPD6599	Discontinued
0.7988	Intermediate Similarity	NPD7199	Phase 2
0.7987	Intermediate Similarity	NPD943	Approved
0.7978	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7961	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7917	Intermediate Similarity	NPD3749	Approved
0.7895	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7861	Intermediate Similarity	NPD7228	Approved
0.7812	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7809	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7797	Intermediate Similarity	NPD8313	Approved
0.7797	Intermediate Similarity	NPD8312	Approved
0.7791	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.779	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD1247	Approved
0.7765	Intermediate Similarity	NPD6234	Discontinued
0.7765	Intermediate Similarity	NPD919	Approved
0.7764	Intermediate Similarity	NPD3750	Approved
0.7764	Intermediate Similarity	NPD4628	Phase 3
0.7759	Intermediate Similarity	NPD3751	Discontinued
0.7758	Intermediate Similarity	NPD1653	Approved
0.775	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7742	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7733	Intermediate Similarity	NPD3787	Discontinued
0.773	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7727	Intermediate Similarity	NPD4908	Phase 1
0.7717	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7716	Intermediate Similarity	NPD6190	Approved
0.7707	Intermediate Similarity	NPD230	Phase 1
0.7688	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7684	Intermediate Similarity	NPD7685	Pre-registration
0.7683	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7679	Intermediate Similarity	NPD37	Approved
0.7647	Intermediate Similarity	NPD4966	Approved
0.7647	Intermediate Similarity	NPD4965	Approved
0.7647	Intermediate Similarity	NPD4967	Phase 2
0.7628	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7625	Intermediate Similarity	NPD1551	Phase 2
0.7625	Intermediate Similarity	NPD2935	Discontinued
0.7625	Intermediate Similarity	NPD6099	Approved
0.7625	Intermediate Similarity	NPD6100	Approved
0.7622	Intermediate Similarity	NPD7390	Discontinued
0.7595	Intermediate Similarity	NPD447	Suspended
0.7593	Intermediate Similarity	NPD2800	Approved
0.7576	Intermediate Similarity	NPD2533	Approved
0.7576	Intermediate Similarity	NPD2534	Approved
0.7576	Intermediate Similarity	NPD2532	Approved
0.7552	Intermediate Similarity	NPD8151	Discontinued
0.7547	Intermediate Similarity	NPD6651	Approved
0.7529	Intermediate Similarity	NPD8455	Phase 2
0.75	Intermediate Similarity	NPD3226	Approved
0.7484	Intermediate Similarity	NPD1933	Approved
0.7473	Intermediate Similarity	NPD8150	Discontinued
0.747	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7469	Intermediate Similarity	NPD7266	Discontinued
0.7469	Intermediate Similarity	NPD2344	Approved
0.7453	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7453	Intermediate Similarity	NPD3748	Approved
0.7448	Intermediate Similarity	NPD7584	Approved
0.7444	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7439	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7436	Intermediate Similarity	NPD9494	Approved
0.743	Intermediate Similarity	NPD5953	Discontinued
0.7419	Intermediate Similarity	NPD4360	Phase 2
0.7419	Intermediate Similarity	NPD4363	Phase 3
0.7416	Intermediate Similarity	NPD7286	Phase 2
0.7407	Intermediate Similarity	NPD6780	Approved
0.7407	Intermediate Similarity	NPD6778	Approved
0.7407	Intermediate Similarity	NPD6776	Approved
0.7407	Intermediate Similarity	NPD6777	Approved
0.7407	Intermediate Similarity	NPD6781	Approved
0.7407	Intermediate Similarity	NPD6782	Approved
0.7407	Intermediate Similarity	NPD6779	Approved
0.7405	Intermediate Similarity	NPD6798	Discontinued
0.7403	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7396	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7389	Intermediate Similarity	NPD6832	Phase 2
0.7389	Intermediate Similarity	NPD7240	Approved
0.7386	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7385	Intermediate Similarity	NPD7783	Phase 2
0.7385	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7382	Intermediate Similarity	NPD7435	Discontinued
0.7381	Intermediate Similarity	NPD920	Approved
0.7377	Intermediate Similarity	NPD8434	Phase 2
0.7371	Intermediate Similarity	NPD8127	Discontinued
0.7368	Intermediate Similarity	NPD6844	Discontinued
0.7346	Intermediate Similarity	NPD7033	Discontinued
0.7346	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7344	Intermediate Similarity	NPD7871	Phase 2
0.7344	Intermediate Similarity	NPD7870	Phase 2
0.7333	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7292	Intermediate Similarity	NPD7698	Approved
0.7292	Intermediate Similarity	NPD7696	Phase 3
0.7292	Intermediate Similarity	NPD7697	Approved
0.7289	Intermediate Similarity	NPD2309	Approved
0.7283	Intermediate Similarity	NPD5353	Approved
0.7273	Intermediate Similarity	NPD1610	Phase 2
0.7273	Intermediate Similarity	NPD1243	Approved
0.7262	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7256	Intermediate Similarity	NPD2346	Discontinued
0.725	Intermediate Similarity	NPD6233	Phase 2
0.7246	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.724	Intermediate Similarity	NPD6823	Phase 2
0.7239	Intermediate Similarity	NPD2799	Discontinued
0.7232	Intermediate Similarity	NPD7229	Phase 3
0.7231	Intermediate Similarity	NPD7701	Phase 2
0.7209	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7198	Intermediate Similarity	NPD7039	Approved
0.7198	Intermediate Similarity	NPD7038	Approved
0.7197	Intermediate Similarity	NPD1203	Approved
0.7193	Intermediate Similarity	NPD7458	Discontinued
0.7191	Intermediate Similarity	NPD5242	Approved
0.7188	Intermediate Similarity	NPD2313	Discontinued
0.7169	Intermediate Similarity	NPD6674	Discontinued
0.7169	Intermediate Similarity	NPD1652	Phase 2
0.716	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD5124	Phase 1
0.716	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD6355	Discontinued
0.7158	Intermediate Similarity	NPD7549	Discontinued
0.7157	Intermediate Similarity	NPD7874	Approved
0.7157	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6534	Approved
0.7143	Intermediate Similarity	NPD6535	Approved
0.7135	Intermediate Similarity	NPD5710	Approved
0.7135	Intermediate Similarity	NPD5711	Approved
0.7124	Intermediate Similarity	NPD1548	Phase 1
0.7121	Intermediate Similarity	NPD7801	Approved
0.712	Intermediate Similarity	NPD7700	Phase 2
0.712	Intermediate Similarity	NPD7699	Phase 2
0.7113	Intermediate Similarity	NPD7680	Approved
0.711	Intermediate Similarity	NPD6385	Approved
0.711	Intermediate Similarity	NPD6386	Approved
0.7108	Intermediate Similarity	NPD2424	Discontinued
0.7107	Intermediate Similarity	NPD2861	Phase 2
0.7107	Intermediate Similarity	NPD3018	Phase 2
0.7083	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD3268	Approved
0.7081	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD7447	Phase 1
0.7059	Intermediate Similarity	NPD4661	Approved
0.7059	Intermediate Similarity	NPD4662	Approved
0.7056	Intermediate Similarity	NPD7585	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