NPASS Compound

Structure

NPC180768 OpenBabel07101718282D 46 50 0 0 1 0 0 0 0 0999 V2000 -3.0878 1.7891 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0878 -3.4071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 1.6910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4152 -1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5491 -1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.8793 -3.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1472 -3.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2361 -5.4223 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5962 -3.7281 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.8793 -4.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1472 -4.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2142 -5.6302 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5743 -3.9360 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2812 -1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 -1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 -0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0878 0.0570 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0878 -1.6750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3090 -2.5691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 -1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0132 -2.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9271 -4.4712 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5878 -0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0132 -4.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8833 -4.8870 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 -1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.6180 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.0878 0.0570 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0878 -1.6750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5878 -0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5878 -0.8090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.9511 -0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0132 -1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0511 -4.2633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0132 -5.8090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.8615 -5.0949 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.5878 -0.8090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.8793 -1.3090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7202 -5.0064 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.5878 0.9230 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.5878 -2.5411 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 1.1910 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.1472 -1.3090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.3601 -3.3122 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 41 1 0 0 0 0 2 42 1 0 0 0 0 3 43 1 0 0 0 0 4 5 2 0 0 0 0 4 14 1 0 0 0 0 5 20 1 0 0 0 0 6 10 1 0 0 0 0 6 21 2 0 0 0 0 7 11 2 0 0 0 0 7 21 1 0 0 0 0 8 12 1 0 0 0 0 8 22 2 0 0 0 0 9 13 2 0 0 0 0 9 22 1 0 0 0 0 10 24 2 0 0 0 0 11 24 1 0 0 0 0 12 25 2 0 0 0 0 13 25 1 0 0 0 0 14 44 1 0 0 0 0 15 20 2 0 0 0 0 15 26 1 0 0 0 0 16 20 1 0 0 0 0 16 30 2 0 0 0 0 17 23 2 0 0 0 0 17 28 1 0 0 0 0 18 23 1 0 0 0 0 18 29 2 0 0 0 0 19 45 1 0 0 0 0 21 34 1 0 0 0 0 22 35 1 0 0 0 0 24 36 1 0 0 0 0 25 37 1 0 0 0 0 26 27 1 0 0 0 0 26 33 2 0 0 0 0 27 19 1 6 0 0 0 27 32 1 0 0 0 0 28 31 2 0 0 0 0 28 41 1 0 0 0 0 29 31 1 0 0 0 0 29 42 1 0 0 0 0 30 33 1 0 0 0 0 30 43 1 0 0 0 0 31 38 1 0 0 0 0 32 23 1 1 0 0 0 32 46 1 0 0 0 0 33 46 1 0 0 0 0 34 39 2 0 0 0 0 34 44 1 0 0 0 0 35 40 2 0 0 0 0 35 45 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	628.19
Volume:	628.279
LogP:	4.817
LogD:	3.612
LogS:	-3.225
# Rotatable Bonds:	13
TPSA:	150.21
# H-Bond Aceptor:	11
# H-Bond Donor:	3
# Rings:	5
# Heavy Atoms:	11

MedChem Properties

QED Drug-Likeness Score:	0.174
Synthetic Accessibility Score:	3.704
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:	-5.006
MDCK Permeability:	4.684367377194576e-05
Pgp-inhibitor:	0.932
Pgp-substrate:	0.011
Human Intestinal Absorption (HIA):	0.015
20% Bioavailability (F20%):	0.015
30% Bioavailability (F30%):	0.057

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.023
Plasma Protein Binding (PPB):	96.8724136352539%
Volume Distribution (VD):	0.342
Pgp-substrate:	6.1501145362854%

ADMET: Metabolism

CYP1A2-inhibitor:	0.126
CYP1A2-substrate:	0.863
CYP2C19-inhibitor:	0.934
CYP2C19-substrate:	0.062
CYP2C9-inhibitor:	0.934
CYP2C9-substrate:	0.965
CYP2D6-inhibitor:	0.333
CYP2D6-substrate:	0.765
CYP3A4-inhibitor:	0.778
CYP3A4-substrate:	0.659

ADMET: Excretion

Clearance (CL):	8.82
Half-life (T1/2):	0.856

ADMET: Toxicity

hERG Blockers:	0.206
Human Hepatotoxicity (H-HT):	0.109
Drug-inuced Liver Injury (DILI):	0.925
AMES Toxicity:	0.056
Rat Oral Acute Toxicity:	0.059
Maximum Recommended Daily Dose:	0.174
Skin Sensitization:	0.954
Carcinogencity:	0.303
Eye Corrosion:	0.003
Eye Irritation:	0.839
Respiratory Toxicity:	0.051

Download Data

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

Natural Product: NPC180768

Natural Product ID:	NPC180768
*Common Name:**	Quiquesetinerviusin B
IUPAC Name:	[(E)-3-[(2S,3R)-3-[(4-hydroxybenzoyl)oxymethyl]-2-(4-hydroxy-3,5-dimethoxyphenyl)-7-methoxy-2,3-dihydro-1-benzofuran-5-yl]prop-2-enyl] 4-hydroxybenzoate
Synonyms:	quiquesetinerviusin B
Standard InCHIKey:	KXDQNTKVSVQRSV-FDMZCADJSA-N
Standard InCHI:	InChI=1S/C35H32O11/c1-41-28-17-23(18-29(42-2)31(28)38)32-27(19-45-35(40)22-8-12-25(37)13-9-22)26-15-20(16-30(43-3)33(26)46-32)5-4-14-44-34(39)21-6-10-24(36)11-7-21/h4-13,15-18,27,32,36-38H,14,19H2,1-3H3/b5-4+/t27-,32+/m0/s1
SMILES:	COc1cc(/C=C/COC(=O)c2ccc(cc2)O)cc2c1O[C@@H]([C@H]2COC(=O)c1ccc(cc1)O)c1cc(OC)c(c(c1)OC)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1224883
PubChem CID:	46938439
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
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
Others	2

Activity Type	# Activity
Cell Line	3
NON-MOLECULAR	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	223200.0	nM	PMID[544627]
NPT113	Cell Line	RAW264.7	Mus musculus	Activity	>	90.0	%	PMID[544627]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	25700.0	nM	PMID[544627]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	200000.0	nM	PMID[544627]

☑ 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 NPC180768 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	380
0.1-0.2	1518
0.2-0.3	3324
0.3-0.4	8193
0.4-0.5	10254
0.5-0.6	3576
0.6-0.7	4780
0.7-0.8	6770
0.8-0.85	3168
0.85-0.9	638
0.9-0.95	90
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
0.9686	High Similarity	NPC45943
0.956	High Similarity	NPC216916
0.95	High Similarity	NPC476371
0.95	High Similarity	NPC476372
0.9394	High Similarity	NPC98583
0.9375	High Similarity	NPC476373
0.9371	High Similarity	NPC125495
0.9333	High Similarity	NPC100251
0.9325	High Similarity	NPC43065
0.9317	High Similarity	NPC469889
0.9273	High Similarity	NPC476365
0.9255	High Similarity	NPC53889
0.9217	High Similarity	NPC65333
0.9193	High Similarity	NPC87317
0.9182	High Similarity	NPC469888
0.9167	High Similarity	NPC79736
0.9167	High Similarity	NPC67629
0.9162	High Similarity	NPC316539
0.913	High Similarity	NPC160512
0.913	High Similarity	NPC68324
0.913	High Similarity	NPC289322
0.913	High Similarity	NPC114179
0.913	High Similarity	NPC156818
0.913	High Similarity	NPC38779
0.9119	High Similarity	NPC115203
0.9112	High Similarity	NPC267549
0.9102	High Similarity	NPC476370
0.9068	High Similarity	NPC250436
0.9068	High Similarity	NPC88803
0.9068	High Similarity	NPC104983
0.9068	High Similarity	NPC291948
0.9068	High Similarity	NPC300845
0.9068	High Similarity	NPC165483
0.9057	High Similarity	NPC267091
0.9048	High Similarity	NPC476374
0.9042	High Similarity	NPC102277
0.9042	High Similarity	NPC279209
0.9036	High Similarity	NPC473818
0.9024	High Similarity	NPC473445
0.9018	High Similarity	NPC24164
0.9012	High Similarity	NPC470827
0.9006	High Similarity	NPC117668
0.9	High Similarity	NPC474656
0.8994	High Similarity	NPC243891
0.8982	High Similarity	NPC475212
0.8982	High Similarity	NPC476279
0.8976	High Similarity	NPC9309
0.897	High Similarity	NPC291977
0.8963	High Similarity	NPC92589
0.8963	High Similarity	NPC109061
0.8957	High Similarity	NPC470828
0.8953	High Similarity	NPC150977
0.8951	High Similarity	NPC318432
0.8938	High Similarity	NPC476434
0.8916	High Similarity	NPC142614
0.8916	High Similarity	NPC471788
0.8916	High Similarity	NPC477840
0.8909	High Similarity	NPC473012
0.8909	High Similarity	NPC42797
0.8909	High Similarity	NPC476247
0.8902	High Similarity	NPC292415
0.8896	High Similarity	NPC35598
0.8896	High Similarity	NPC222689
0.8876	High Similarity	NPC174700
0.8869	High Similarity	NPC41494
0.8869	High Similarity	NPC186100
0.8869	High Similarity	NPC216403
0.8862	High Similarity	NPC13481
0.8862	High Similarity	NPC171985
0.8862	High Similarity	NPC472452
0.8862	High Similarity	NPC320741
0.8862	High Similarity	NPC471823
0.8862	High Similarity	NPC207575
0.8862	High Similarity	NPC224851
0.8855	High Similarity	NPC473009
0.8848	High Similarity	NPC142252
0.8848	High Similarity	NPC158188
0.8848	High Similarity	NPC312273
0.8848	High Similarity	NPC473106
0.8848	High Similarity	NPC301256
0.8848	High Similarity	NPC124747
0.8848	High Similarity	NPC155754
0.8848	High Similarity	NPC103201
0.8841	High Similarity	NPC7543
0.8841	High Similarity	NPC94220
0.8841	High Similarity	NPC98083
0.8841	High Similarity	NPC166456
0.8841	High Similarity	NPC24339
0.8837	High Similarity	NPC471030
0.882	High Similarity	NPC75695
0.8817	High Similarity	NPC91043
0.881	High Similarity	NPC311912
0.8805	High Similarity	NPC252402
0.8805	High Similarity	NPC102934
0.8802	High Similarity	NPC473010
0.8802	High Similarity	NPC472277
0.88	High Similarity	NPC73929
0.88	High Similarity	NPC47905
0.88	High Similarity	NPC139683
0.8795	High Similarity	NPC477841
0.8795	High Similarity	NPC249070
0.8795	High Similarity	NPC472635
0.8795	High Similarity	NPC201800
0.8795	High Similarity	NPC219927
0.8795	High Similarity	NPC149389
0.8788	High Similarity	NPC328102
0.8788	High Similarity	NPC24627
0.8788	High Similarity	NPC472624
0.8786	High Similarity	NPC53680
0.8786	High Similarity	NPC125352
0.8786	High Similarity	NPC208797
0.878	High Similarity	NPC291508
0.8779	High Similarity	NPC477882
0.8779	High Similarity	NPC477880
0.8773	High Similarity	NPC203757
0.8773	High Similarity	NPC300757
0.8773	High Similarity	NPC180901
0.8773	High Similarity	NPC222185
0.8765	High Similarity	NPC289396
0.8765	High Similarity	NPC199773
0.8765	High Similarity	NPC212038
0.8765	High Similarity	NPC131121
0.8765	High Similarity	NPC186847
0.8765	High Similarity	NPC271848
0.8765	High Similarity	NPC257667
0.8765	High Similarity	NPC4200
0.8765	High Similarity	NPC81332
0.8765	High Similarity	NPC262580
0.8765	High Similarity	NPC470769
0.8765	High Similarity	NPC472454
0.8764	High Similarity	NPC476358
0.8757	High Similarity	NPC288813
0.8757	High Similarity	NPC88557
0.8757	High Similarity	NPC107627
0.8757	High Similarity	NPC264302
0.875	High Similarity	NPC475250
0.875	High Similarity	NPC235610
0.8743	High Similarity	NPC100425
0.8743	High Similarity	NPC304322
0.8743	High Similarity	NPC205265
0.8743	High Similarity	NPC472281
0.8743	High Similarity	NPC124038
0.8743	High Similarity	NPC173729
0.8743	High Similarity	NPC272750
0.8743	High Similarity	NPC18100
0.8743	High Similarity	NPC112380
0.8743	High Similarity	NPC223006
0.8743	High Similarity	NPC134047
0.8736	High Similarity	NPC129533
0.8736	High Similarity	NPC123259
0.8736	High Similarity	NPC321916
0.8736	High Similarity	NPC199172
0.8736	High Similarity	NPC35924
0.8735	High Similarity	NPC139540
0.8735	High Similarity	NPC26326
0.8735	High Similarity	NPC471211
0.8735	High Similarity	NPC471210
0.8735	High Similarity	NPC349525
0.8735	High Similarity	NPC471212
0.8735	High Similarity	NPC177100
0.8735	High Similarity	NPC472634
0.8728	High Similarity	NPC185275
0.8728	High Similarity	NPC80956
0.8728	High Similarity	NPC324742
0.8727	High Similarity	NPC172202
0.8727	High Similarity	NPC284127
0.8727	High Similarity	NPC476410
0.8721	High Similarity	NPC472723
0.8721	High Similarity	NPC156955
0.872	High Similarity	NPC470328
0.872	High Similarity	NPC209614
0.872	High Similarity	NPC195796
0.872	High Similarity	NPC472626
0.872	High Similarity	NPC278778
0.872	High Similarity	NPC291878
0.872	High Similarity	NPC35038
0.8713	High Similarity	NPC172033
0.8713	High Similarity	NPC175230
0.8713	High Similarity	NPC88560
0.8706	High Similarity	NPC131866
0.8698	High Similarity	NPC150131
0.8698	High Similarity	NPC215802
0.8698	High Similarity	NPC167231
0.8696	High Similarity	NPC473091
0.869	High Similarity	NPC300053
0.869	High Similarity	NPC108433
0.869	High Similarity	NPC293319
0.8686	High Similarity	NPC318119
0.8683	High Similarity	NPC174311
0.8683	High Similarity	NPC474033
0.8683	High Similarity	NPC474162
0.8683	High Similarity	NPC261896
0.8683	High Similarity	NPC474034
0.8683	High Similarity	NPC33298
0.8683	High Similarity	NPC285108
0.8683	High Similarity	NPC474150
0.8683	High Similarity	NPC81679
0.8683	High Similarity	NPC144557
0.8678	High Similarity	NPC469371
0.8678	High Similarity	NPC8940

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 NPC180768 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	328
0.1-0.2	913
0.2-0.3	1677
0.3-0.4	2573
0.4-0.5	1891
0.5-0.6	1040
0.6-0.7	526
0.7-0.8	154
0.8-0.85	36
0.85-0.9	11
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9068	High Similarity	NPD4868	Clinical (unspecified phase)
0.8765	High Similarity	NPD7993	Clinical (unspecified phase)
0.8757	High Similarity	NPD5844	Phase 1
0.8598	High Similarity	NPD2393	Clinical (unspecified phase)
0.858	High Similarity	NPD6166	Phase 2
0.858	High Similarity	NPD6168	Clinical (unspecified phase)
0.858	High Similarity	NPD6167	Clinical (unspecified phase)
0.8537	High Similarity	NPD1934	Approved
0.8529	High Similarity	NPD7473	Discontinued
0.8494	Intermediate Similarity	NPD7768	Phase 2
0.848	Intermediate Similarity	NPD3818	Discontinued
0.8462	Intermediate Similarity	NPD6232	Discontinued
0.8452	Intermediate Similarity	NPD5494	Approved
0.8443	Intermediate Similarity	NPD7075	Discontinued
0.8434	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8383	Intermediate Similarity	NPD3882	Suspended
0.8382	Intermediate Similarity	NPD7074	Phase 3
0.8373	Intermediate Similarity	NPD1465	Phase 2
0.8373	Intermediate Similarity	NPD7819	Suspended
0.8363	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8324	Intermediate Similarity	NPD7054	Approved
0.8323	Intermediate Similarity	NPD3817	Phase 2
0.8305	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.8294	Intermediate Similarity	NPD7199	Phase 2
0.8284	Intermediate Similarity	NPD6234	Discontinued
0.8276	Intermediate Similarity	NPD7472	Approved
0.8268	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.8263	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8263	Intermediate Similarity	NPD2801	Approved
0.8253	Intermediate Similarity	NPD7411	Suspended
0.8232	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.8198	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.8193	Intermediate Similarity	NPD4380	Phase 2
0.8187	Intermediate Similarity	NPD6959	Discontinued
0.8161	Intermediate Similarity	NPD7228	Approved
0.8136	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8136	Intermediate Similarity	NPD7808	Phase 3
0.8095	Intermediate Similarity	NPD6801	Discontinued
0.8095	Intermediate Similarity	NPD37	Approved
0.8079	Intermediate Similarity	NPD7251	Discontinued
0.8079	Intermediate Similarity	NPD6559	Discontinued
0.8059	Intermediate Similarity	NPD4967	Phase 2
0.8059	Intermediate Similarity	NPD4966	Approved
0.8059	Intermediate Similarity	NPD4965	Approved
0.8049	Intermediate Similarity	NPD1511	Approved
0.8025	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.8023	Intermediate Similarity	NPD6797	Phase 2
0.8012	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8011	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7989	Intermediate Similarity	NPD8313	Approved
0.7989	Intermediate Similarity	NPD8312	Approved
0.7978	Intermediate Similarity	NPD7685	Pre-registration
0.7977	Intermediate Similarity	NPD8127	Discontinued
0.7952	Intermediate Similarity	NPD1512	Approved
0.7941	Intermediate Similarity	NPD8455	Phase 2
0.7939	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7907	Intermediate Similarity	NPD3749	Approved
0.7892	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7866	Intermediate Similarity	NPD3750	Approved
0.7866	Intermediate Similarity	NPD4628	Phase 3
0.7861	Intermediate Similarity	NPD919	Approved
0.7831	Intermediate Similarity	NPD6799	Approved
0.7829	Intermediate Similarity	NPD7229	Phase 3
0.7812	Intermediate Similarity	NPD230	Phase 1
0.7791	Intermediate Similarity	NPD5402	Approved
0.7784	Intermediate Similarity	NPD2532	Approved
0.7784	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7784	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7784	Intermediate Similarity	NPD2534	Approved
0.7784	Intermediate Similarity	NPD2533	Approved
0.7765	Intermediate Similarity	NPD6599	Discontinued
0.7744	Intermediate Similarity	NPD1549	Phase 2
0.7736	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7711	Intermediate Similarity	NPD6190	Approved
0.7706	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7706	Intermediate Similarity	NPD7458	Discontinued
0.7692	Intermediate Similarity	NPD5403	Approved
0.7684	Intermediate Similarity	NPD3926	Phase 2
0.7683	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7683	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.768	Intermediate Similarity	NPD7240	Approved
0.7663	Intermediate Similarity	NPD8434	Phase 2
0.7651	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD1653	Approved
0.764	Intermediate Similarity	NPD1613	Approved
0.764	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7636	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7625	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7622	Intermediate Similarity	NPD2935	Discontinued
0.7622	Intermediate Similarity	NPD2796	Approved
0.7619	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7574	Intermediate Similarity	NPD5401	Approved
0.7571	Intermediate Similarity	NPD1247	Approved
0.7562	Intermediate Similarity	NPD3027	Phase 3
0.7561	Intermediate Similarity	NPD1510	Phase 2
0.7561	Intermediate Similarity	NPD3748	Approved
0.7551	Intermediate Similarity	NPD8151	Discontinued
0.7545	Intermediate Similarity	NPD8166	Discontinued
0.7529	Intermediate Similarity	NPD6273	Approved
0.75	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD3226	Approved
0.75	Intermediate Similarity	NPD4908	Phase 1
0.7485	Intermediate Similarity	NPD920	Approved
0.7485	Intermediate Similarity	NPD6355	Discontinued
0.7474	Intermediate Similarity	NPD7680	Approved
0.7473	Intermediate Similarity	NPD8150	Discontinued
0.7471	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7459	Intermediate Similarity	NPD7177	Discontinued
0.744	Intermediate Similarity	NPD7003	Approved
0.7438	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7423	Intermediate Similarity	NPD1240	Approved
0.7414	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7412	Intermediate Similarity	NPD7390	Discontinued
0.741	Intermediate Similarity	NPD1551	Phase 2
0.7407	Intermediate Similarity	NPD6798	Discontinued
0.7389	Intermediate Similarity	NPD5242	Approved
0.7386	Intermediate Similarity	NPD5353	Approved
0.7381	Intermediate Similarity	NPD1243	Approved
0.7381	Intermediate Similarity	NPD2800	Approved
0.7378	Intermediate Similarity	NPD447	Suspended
0.7368	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7366	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD7266	Discontinued
0.7365	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7358	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7353	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7351	Intermediate Similarity	NPD7549	Discontinued
0.7349	Intermediate Similarity	NPD2799	Discontinued
0.7337	Intermediate Similarity	NPD5953	Discontinued
0.7333	Intermediate Similarity	NPD1607	Approved
0.7322	Intermediate Similarity	NPD7286	Phase 2
0.732	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD4060	Phase 1
0.7317	Intermediate Similarity	NPD943	Approved
0.7305	Intermediate Similarity	NPD5405	Approved
0.7305	Intermediate Similarity	NPD5404	Approved
0.7305	Intermediate Similarity	NPD6100	Approved
0.7305	Intermediate Similarity	NPD5406	Approved
0.7305	Intermediate Similarity	NPD5408	Approved
0.7305	Intermediate Similarity	NPD6099	Approved
0.7301	Intermediate Similarity	NPD3764	Approved
0.73	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.73	Intermediate Similarity	NPD7783	Phase 2
0.7296	Intermediate Similarity	NPD7435	Discontinued
0.7273	Intermediate Similarity	NPD5124	Phase 1
0.7273	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7268	Intermediate Similarity	NPD3751	Discontinued
0.7258	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7256	Intermediate Similarity	NPD6233	Phase 2
0.7238	Intermediate Similarity	NPD5710	Approved
0.7238	Intermediate Similarity	NPD3787	Discontinued
0.7238	Intermediate Similarity	NPD5711	Approved
0.7235	Intermediate Similarity	NPD4110	Phase 3
0.7235	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7233	Intermediate Similarity	NPD1608	Approved
0.7222	Intermediate Similarity	NPD9494	Approved
0.7216	Intermediate Similarity	NPD6386	Approved
0.7216	Intermediate Similarity	NPD6385	Approved
0.7205	Intermediate Similarity	NPD2797	Approved
0.7204	Intermediate Similarity	NPD7038	Approved
0.7204	Intermediate Similarity	NPD7039	Approved
0.7195	Intermediate Similarity	NPD3268	Approved
0.7186	Intermediate Similarity	NPD7097	Phase 1
0.7178	Intermediate Similarity	NPD6832	Phase 2
0.7176	Intermediate Similarity	NPD6674	Discontinued
0.7172	Intermediate Similarity	NPD7871	Phase 2
0.7172	Intermediate Similarity	NPD7870	Phase 2
0.7169	Intermediate Similarity	NPD1933	Approved
0.7164	Intermediate Similarity	NPD7874	Approved
0.7164	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD6004	Phase 3
0.716	Intermediate Similarity	NPD2346	Discontinued
0.716	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD6002	Phase 3
0.716	Intermediate Similarity	NPD2344	Approved
0.716	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD6005	Phase 3
0.715	Intermediate Similarity	NPD7585	Approved
0.7143	Intermediate Similarity	NPD7033	Discontinued
0.7143	Intermediate Similarity	NPD6782	Approved
0.7143	Intermediate Similarity	NPD6780	Approved
0.7143	Intermediate Similarity	NPD6779	Approved
0.7143	Intermediate Similarity	NPD6778	Approved
0.7143	Intermediate Similarity	NPD6781	Approved
0.7143	Intermediate Similarity	NPD6777	Approved
0.7143	Intermediate Similarity	NPD6776	Approved
0.7126	Intermediate Similarity	NPD6651	Approved
0.7125	Intermediate Similarity	NPD9269	Phase 2
0.7121	Intermediate Similarity	NPD7696	Phase 3
0.7121	Intermediate Similarity	NPD7697	Approved
0.7121	Intermediate Similarity	NPD7698	Approved
0.7111	Intermediate Similarity	NPD6971	Discontinued
0.71	Intermediate Similarity	NPD7583	Approved
0.7095	Intermediate Similarity	NPD4288	Approved
0.7091	Intermediate Similarity	NPD2313	Discontinued
0.7085	Intermediate Similarity	NPD8319	Approved
0.7085	Intermediate Similarity	NPD8320	Phase 1
0.7081	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD7893	Clinical (unspecified phase)

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