NPASS Compound

Structure

CID177308 OpenBabel06191715552D 31 34 0 0 1 0 0 0 0 0999 V2000 5.1962 3.0000 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 6.0622 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 2.0000 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 -1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 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 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 -0.8660 0.5000 0.0000 C 0 0 2 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 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 -0.8660 1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 2.0000 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 2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 1 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 7.7942 3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -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 0.0000 0.0000 O 0 0 0 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 -0.0000 3.0000 0.0000 O 0 0 0 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 2.5981 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 8 2 0 0 0 0 2 4 2 0 0 0 0 2 8 1 0 0 0 0 3 9 2 0 0 0 0 4 9 1 0 0 0 0 5 11 2 0 0 0 0 5 12 1 0 0 0 0 6 22 1 0 0 0 0 7 10 2 0 0 0 0 7 30 1 0 0 0 0 8 10 1 0 0 0 0 9 23 1 0 0 0 0 10 16 1 0 0 0 0 11 14 1 0 0 0 0 11 24 1 0 0 0 0 12 15 2 0 0 0 0 12 25 1 0 0 0 0 13 6 1 6 0 0 0 13 17 1 0 0 0 0 13 31 1 0 0 0 0 14 16 1 0 0 0 0 14 20 2 0 0 0 0 15 20 1 0 0 0 0 16 26 2 0 0 0 0 17 18 1 0 0 0 0 17 27 1 1 0 0 0 18 19 1 0 0 0 0 18 28 1 6 0 0 0 19 21 1 0 0 0 0 19 29 1 1 0 0 0 20 30 1 0 0 0 0 21 15 1 6 0 0 0 21 31 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	432.11
Volume:	404.357
LogP:	0.549
LogD:	0.474
LogS:	-3.86
# Rotatable Bonds:	3
TPSA:	181.05
# H-Bond Aceptor:	10
# H-Bond Donor:	7
# Rings:	4
# Heavy Atoms:	10

MedChem Properties

QED Drug-Likeness Score:	0.3
Synthetic Accessibility Score:	4.005
Fsp3:	0.286
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.292
MDCK Permeability:	4.753023858938832e-06
Pgp-inhibitor:	0.005
Pgp-substrate:	0.985
Human Intestinal Absorption (HIA):	0.806
20% Bioavailability (F20%):	0.668
30% Bioavailability (F30%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.022
Plasma Protein Binding (PPB):	91.6653060913086%
Volume Distribution (VD):	0.786
Pgp-substrate:	8.839728355407715%

ADMET: Metabolism

CYP1A2-inhibitor:	0.121
CYP1A2-substrate:	0.034
CYP2C19-inhibitor:	0.026
CYP2C19-substrate:	0.049
CYP2C9-inhibitor:	0.107
CYP2C9-substrate:	0.436
CYP2D6-inhibitor:	0.264
CYP2D6-substrate:	0.16
CYP3A4-inhibitor:	0.083
CYP3A4-substrate:	0.016

ADMET: Excretion

Clearance (CL):	4.371
Half-life (T1/2):	0.847

ADMET: Toxicity

hERG Blockers:	0.112
Human Hepatotoxicity (H-HT):	0.174
Drug-inuced Liver Injury (DILI):	0.961
AMES Toxicity:	0.729
Rat Oral Acute Toxicity:	0.246
Maximum Recommended Daily Dose:	0.007
Skin Sensitization:	0.674
Carcinogencity:	0.091
Eye Corrosion:	0.003
Eye Irritation:	0.085
Respiratory Toxicity:	0.047

Download Data

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

Natural Product: NPC177308

Natural Product ID:	NPC177308
*Common Name:**	Genistein 8-C-Beta-D-Glucoside
IUPAC Name:	5,7-dihydroxy-3-(4-hydroxyphenyl)-8-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]chromen-4-one
Synonyms:
Standard InCHIKey:	HIWJJOYYZFELEZ-FFYOZGDPSA-N
Standard InCHI:	InChI=1S/C21H20O10/c22-6-13-17(27)18(28)19(29)21(31-13)15-12(25)5-11(24)14-16(26)10(7-30-20(14)15)8-1-3-9(23)4-2-8/h1-5,7,13,17-19,21-25,27-29H,6H2/t13-,17-,18+,19-,21+/m1/s1
SMILES:	c1cc(ccc1c1coc2c(c(cc(c2[C@H]2[C@@H]([C@H]([C@@H]([C@@H](CO)O2)O)O)O)O)O)c1=O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1945734
PubChem CID:	5281757
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0002506] Isoflavonoids [CHEMONTID:0002896] Isoflavonoid C-glycosides

*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
NPO1830	Dalbergia sissoo	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18154272]
NPO11067	Buxus papillosa	Species	Buxaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20954721]
NPO4886	Coniochaeta saccardoi	Species	Coniochaetaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21082806]
NPO1830	Dalbergia sissoo	Species	Fabaceae	Eukaryota	leaves	n.a.	n.a.	PMID[22212722]
NPO30303	Pueraria lobata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25679337]
NPO11067	Buxus papillosa	Species	Buxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO30303	Pueraria lobata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO1830	Dalbergia sissoo	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11067	Buxus papillosa	Species	Buxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1830	Dalbergia sissoo	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO30303	Pueraria lobata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO1830	Dalbergia sissoo	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO10255	Ipomoea muricata	Species	Convolvulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4886	Coniochaeta saccardoi	Species	Coniochaetaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1830	Dalbergia sissoo	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7873	Artemisia sibirica	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22983	Calicotome villosa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11067	Buxus papillosa	Species	Buxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	1
Others	8

Activity Type	# Activity
Cell Line	1
Individual Protein	1
Others	7

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT520	Cell Line	3T3-L1	Mus musculus	FC	=	1.5	n.a.	PMID[565733]
NPT66	Individual Protein	Acetylcholinesterase	Electrophorus electricus	Inhibition	=	26.0	%	PMID[565737]
NPT27	Others	Unspecified		Ratio IC50	=	10.0	n.a.	PMID[565735]
NPT27	Others	Unspecified		IC50	=	1250.0	ug.mL-1	PMID[565735]
NPT2	Others	Unspecified		Activity	=	110.0	%	PMID[565737]
NPT2	Others	Unspecified		Inhibition	=	14.0	%	PMID[565737]
NPT2	Others	Unspecified		Inhibition	=	23.0	%	PMID[565737]
NPT27	Others	Unspecified		logPeff	=	-4.63	n.a.	PMID[565737]
NPT35	Others	n.a.		LogD	=	-0.1	n.a.	PMID[565737]

☑ 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 NPC177308 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	438
0.1-0.2	1674
0.2-0.3	3667
0.3-0.4	9426
0.4-0.5	9291
0.5-0.6	4004
0.6-0.7	5458
0.7-0.8	4601
0.8-0.85	2592
0.85-0.9	1338
0.9-0.95	192
0.95-1	16

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC124478
0.9793	High Similarity	NPC477897
0.9793	High Similarity	NPC328740
0.9793	High Similarity	NPC289774
0.9793	High Similarity	NPC209846
0.9792	High Similarity	NPC89442
0.9726	High Similarity	NPC244583
0.9726	High Similarity	NPC56232
0.9726	High Similarity	NPC161881
0.9726	High Similarity	NPC10807
0.9726	High Similarity	NPC150123
0.966	High Similarity	NPC472583
0.966	High Similarity	NPC7989
0.966	High Similarity	NPC326592
0.966	High Similarity	NPC109594
0.966	High Similarity	NPC268193
0.966	High Similarity	NPC223701
0.966	High Similarity	NPC112701
0.9595	High Similarity	NPC304745
0.9595	High Similarity	NPC470681
0.9595	High Similarity	NPC111341
0.953	High Similarity	NPC471787
0.9527	High Similarity	NPC469405
0.9524	High Similarity	NPC263384
0.9524	High Similarity	NPC471676
0.9524	High Similarity	NPC472420
0.9524	High Similarity	NPC472422
0.9524	High Similarity	NPC244577
0.9517	High Similarity	NPC222298
0.9517	High Similarity	NPC51070
0.9463	High Similarity	NPC217706
0.9463	High Similarity	NPC304207
0.9463	High Similarity	NPC207809
0.9463	High Similarity	NPC259710
0.9463	High Similarity	NPC48579
0.9463	High Similarity	NPC477958
0.9459	High Similarity	NPC475790
0.9459	High Similarity	NPC171651
0.9459	High Similarity	NPC243171
0.9459	High Similarity	NPC35567
0.9452	High Similarity	NPC10097
0.9448	High Similarity	NPC316769
0.9444	High Similarity	NPC476178
0.9444	High Similarity	NPC117836
0.9444	High Similarity	NPC51887
0.9444	High Similarity	NPC475705
0.9404	High Similarity	NPC53545
0.9404	High Similarity	NPC117418
0.94	High Similarity	NPC208152
0.94	High Similarity	NPC78492
0.9396	High Similarity	NPC244250
0.9396	High Similarity	NPC20907
0.9396	High Similarity	NPC248793
0.9396	High Similarity	NPC293286
0.9396	High Similarity	NPC180301
0.9392	High Similarity	NPC474021
0.9392	High Similarity	NPC254412
0.9392	High Similarity	NPC262038
0.9392	High Similarity	NPC319910
0.9392	High Similarity	NPC278476
0.9392	High Similarity	NPC471677
0.9392	High Similarity	NPC474023
0.9392	High Similarity	NPC262039
0.9388	High Similarity	NPC307052
0.9388	High Similarity	NPC139966
0.9342	High Similarity	NPC472320
0.9338	High Similarity	NPC161749
0.9338	High Similarity	NPC197896
0.9338	High Similarity	NPC313163
0.9338	High Similarity	NPC258035
0.9338	High Similarity	NPC156457
0.9333	High Similarity	NPC477530
0.9329	High Similarity	NPC217149
0.9329	High Similarity	NPC476238
0.9329	High Similarity	NPC31627
0.9329	High Similarity	NPC138288
0.9329	High Similarity	NPC285623
0.9329	High Similarity	NPC216035
0.9329	High Similarity	NPC473996
0.9329	High Similarity	NPC327269
0.9324	High Similarity	NPC105136
0.9315	High Similarity	NPC472629
0.9306	High Similarity	NPC321980
0.9306	High Similarity	NPC469404
0.9306	High Similarity	NPC470087
0.9281	High Similarity	NPC97812
0.9281	High Similarity	NPC289771
0.9281	High Similarity	NPC47923
0.9281	High Similarity	NPC26326
0.9276	High Similarity	NPC73511
0.9276	High Similarity	NPC123544
0.9272	High Similarity	NPC215917
0.9272	High Similarity	NPC10754
0.9272	High Similarity	NPC20530
0.9267	High Similarity	NPC236756
0.9267	High Similarity	NPC311579
0.9262	High Similarity	NPC472580
0.9262	High Similarity	NPC474744
0.9262	High Similarity	NPC472423
0.9262	High Similarity	NPC472636
0.9262	High Similarity	NPC471675
0.9262	High Similarity	NPC474772
0.9257	High Similarity	NPC472628
0.9257	High Similarity	NPC5173
0.9252	High Similarity	NPC473077
0.9252	High Similarity	NPC85773
0.9252	High Similarity	NPC296998
0.9252	High Similarity	NPC472627
0.9252	High Similarity	NPC23728
0.9252	High Similarity	NPC110303
0.9247	High Similarity	NPC470890
0.9247	High Similarity	NPC224714
0.9247	High Similarity	NPC124780
0.9247	High Similarity	NPC87486
0.9236	High Similarity	NPC215311
0.9236	High Similarity	NPC172250
0.9236	High Similarity	NPC219917
0.9236	High Similarity	NPC213659
0.9236	High Similarity	NPC259166
0.9236	High Similarity	NPC144118
0.9236	High Similarity	NPC80962
0.9236	High Similarity	NPC204985
0.9236	High Similarity	NPC326109
0.9236	High Similarity	NPC48624
0.9221	High Similarity	NPC131745
0.9221	High Similarity	NPC44947
0.9216	High Similarity	NPC475784
0.9216	High Similarity	NPC306978
0.9216	High Similarity	NPC471976
0.9211	High Similarity	NPC23817
0.9205	High Similarity	NPC476169
0.92	High Similarity	NPC477957
0.92	High Similarity	NPC256141
0.92	High Similarity	NPC324233
0.92	High Similarity	NPC323626
0.9195	High Similarity	NPC472633
0.9195	High Similarity	NPC472421
0.9195	High Similarity	NPC61258
0.9189	High Similarity	NPC168085
0.9189	High Similarity	NPC132592
0.9189	High Similarity	NPC160821
0.9189	High Similarity	NPC6511
0.9184	High Similarity	NPC267375
0.9184	High Similarity	NPC312973
0.9184	High Similarity	NPC88964
0.9184	High Similarity	NPC111786
0.9184	High Similarity	NPC301276
0.9184	High Similarity	NPC474302
0.9184	High Similarity	NPC1940
0.9184	High Similarity	NPC54577
0.9184	High Similarity	NPC475052
0.9184	High Similarity	NPC83357
0.9184	High Similarity	NPC195621
0.9184	High Similarity	NPC470647
0.9184	High Similarity	NPC67805
0.9184	High Similarity	NPC176229
0.9184	High Similarity	NPC142405
0.9184	High Similarity	NPC246948
0.9184	High Similarity	NPC148011
0.9184	High Similarity	NPC20488
0.9184	High Similarity	NPC214774
0.9178	High Similarity	NPC175504
0.9178	High Similarity	NPC149026
0.9178	High Similarity	NPC143896
0.9178	High Similarity	NPC75049
0.9178	High Similarity	NPC150408
0.9178	High Similarity	NPC91560
0.9178	High Similarity	NPC245482
0.9178	High Similarity	NPC68104
0.9178	High Similarity	NPC39329
0.9178	High Similarity	NPC257097
0.9178	High Similarity	NPC169591
0.9178	High Similarity	NPC221432
0.9178	High Similarity	NPC310130
0.9178	High Similarity	NPC301751
0.9178	High Similarity	NPC164980
0.9172	High Similarity	NPC268204
0.9172	High Similarity	NPC52789
0.9172	High Similarity	NPC470089
0.9172	High Similarity	NPC26051
0.9172	High Similarity	NPC55832
0.9167	High Similarity	NPC470211
0.9167	High Similarity	NPC295384
0.9167	High Similarity	NPC283429
0.9161	High Similarity	NPC66087
0.9161	High Similarity	NPC278419
0.9161	High Similarity	NPC179198
0.9161	High Similarity	NPC183672
0.9161	High Similarity	NPC124155
0.9161	High Similarity	NPC257566
0.9156	High Similarity	NPC142252
0.9156	High Similarity	NPC474038
0.9156	High Similarity	NPC303913
0.9156	High Similarity	NPC3629
0.9145	High Similarity	NPC170475
0.9145	High Similarity	NPC45165
0.9139	High Similarity	NPC143851
0.9139	High Similarity	NPC29763
0.9139	High Similarity	NPC39360
0.9139	High Similarity	NPC210003

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 NPC177308 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	410
0.1-0.2	871
0.2-0.3	1723
0.3-0.4	2663
0.4-0.5	1924
0.5-0.6	1035
0.6-0.7	337
0.7-0.8	131
0.8-0.85	35
0.85-0.9	19
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
1.0	High Similarity	NPD4380	Phase 2
0.9338	High Similarity	NPD4381	Clinical (unspecified phase)
0.9085	High Similarity	NPD7075	Discontinued
0.9021	High Similarity	NPD1510	Phase 2
0.9013	High Similarity	NPD2393	Clinical (unspecified phase)
0.8986	High Similarity	NPD4378	Clinical (unspecified phase)
0.8966	High Similarity	NPD1549	Phase 2
0.8947	High Similarity	NPD6801	Discontinued
0.8931	High Similarity	NPD7804	Clinical (unspecified phase)
0.8897	High Similarity	NPD1550	Clinical (unspecified phase)
0.8897	High Similarity	NPD1552	Clinical (unspecified phase)
0.8889	High Similarity	NPD7096	Clinical (unspecified phase)
0.8859	High Similarity	NPD7410	Clinical (unspecified phase)
0.8831	High Similarity	NPD8443	Clinical (unspecified phase)
0.8824	High Similarity	NPD1934	Approved
0.8758	High Similarity	NPD7411	Suspended
0.8742	High Similarity	NPD6167	Clinical (unspecified phase)
0.8742	High Similarity	NPD6166	Phase 2
0.8742	High Similarity	NPD6168	Clinical (unspecified phase)
0.8699	High Similarity	NPD2796	Approved
0.8634	High Similarity	NPD3818	Discontinued
0.8618	High Similarity	NPD5403	Approved
0.8611	High Similarity	NPD1240	Approved
0.858	High Similarity	NPD7054	Approved
0.8543	High Similarity	NPD1511	Approved
0.8535	High Similarity	NPD4868	Clinical (unspecified phase)
0.8528	High Similarity	NPD7472	Approved
0.8528	High Similarity	NPD7074	Phase 3
0.8526	High Similarity	NPD2801	Approved
0.8526	High Similarity	NPD7819	Suspended
0.8493	Intermediate Similarity	NPD1607	Approved
0.8487	Intermediate Similarity	NPD5401	Approved
0.8476	Intermediate Similarity	NPD6797	Phase 2
0.8471	Intermediate Similarity	NPD5402	Approved
0.8438	Intermediate Similarity	NPD6959	Discontinued
0.8431	Intermediate Similarity	NPD1512	Approved
0.8424	Intermediate Similarity	NPD7251	Discontinued
0.8424	Intermediate Similarity	NPD6559	Discontinued
0.8421	Intermediate Similarity	NPD6799	Approved
0.8395	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8375	Intermediate Similarity	NPD5494	Approved
0.8373	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8373	Intermediate Similarity	NPD7808	Phase 3
0.8354	Intermediate Similarity	NPD3817	Phase 2
0.8302	Intermediate Similarity	NPD3882	Suspended
0.8224	Intermediate Similarity	NPD3750	Approved
0.8217	Intermediate Similarity	NPD6599	Discontinued
0.8187	Intermediate Similarity	NPD7768	Phase 2
0.816	Intermediate Similarity	NPD6232	Discontinued
0.8144	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8133	Intermediate Similarity	NPD5844	Phase 1
0.8121	Intermediate Similarity	NPD7473	Discontinued
0.8079	Intermediate Similarity	NPD2935	Discontinued
0.8039	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.8025	Intermediate Similarity	NPD3749	Approved
0.8	Intermediate Similarity	NPD6651	Approved
0.7989	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7987	Intermediate Similarity	NPD4628	Phase 3
0.7987	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7974	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7961	Intermediate Similarity	NPD1551	Phase 2
0.7922	Intermediate Similarity	NPD2800	Approved
0.7911	Intermediate Similarity	NPD920	Approved
0.791	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7898	Intermediate Similarity	NPD2532	Approved
0.7898	Intermediate Similarity	NPD2533	Approved
0.7898	Intermediate Similarity	NPD2534	Approved
0.7898	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7895	Intermediate Similarity	NPD3748	Approved
0.7885	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7867	Intermediate Similarity	NPD943	Approved
0.7852	Intermediate Similarity	NPD2313	Discontinued
0.784	Intermediate Similarity	NPD1465	Phase 2
0.7836	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7824	Intermediate Similarity	NPD5953	Discontinued
0.7814	Intermediate Similarity	NPD7584	Approved
0.7806	Intermediate Similarity	NPD1243	Approved
0.7797	Intermediate Similarity	NPD4363	Phase 3
0.7797	Intermediate Similarity	NPD4360	Phase 2
0.7791	Intermediate Similarity	NPD8312	Approved
0.7791	Intermediate Similarity	NPD8313	Approved
0.7748	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7748	Intermediate Similarity	NPD1613	Approved
0.7733	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7733	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7724	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7722	Intermediate Similarity	NPD7390	Discontinued
0.7706	Intermediate Similarity	NPD7286	Phase 2
0.768	Intermediate Similarity	NPD6782	Approved
0.768	Intermediate Similarity	NPD6777	Approved
0.768	Intermediate Similarity	NPD6781	Approved
0.768	Intermediate Similarity	NPD6776	Approved
0.768	Intermediate Similarity	NPD6778	Approved
0.768	Intermediate Similarity	NPD6780	Approved
0.768	Intermediate Similarity	NPD6779	Approved
0.7665	Intermediate Similarity	NPD1247	Approved
0.7662	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7662	Intermediate Similarity	NPD2799	Discontinued
0.7651	Intermediate Similarity	NPD919	Approved
0.7647	Intermediate Similarity	NPD3751	Discontinued
0.7622	Intermediate Similarity	NPD8455	Phase 2
0.76	Intermediate Similarity	NPD4908	Phase 1
0.7593	Intermediate Similarity	NPD7458	Discontinued
0.7593	Intermediate Similarity	NPD3226	Approved
0.7584	Intermediate Similarity	NPD2798	Approved
0.7582	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7582	Intermediate Similarity	NPD5124	Phase 1
0.7578	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7571	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7564	Intermediate Similarity	NPD2344	Approved
0.7557	Intermediate Similarity	NPD8150	Discontinued
0.7554	Intermediate Similarity	NPD7435	Discontinued
0.755	Intermediate Similarity	NPD3027	Phase 3
0.7548	Intermediate Similarity	NPD7033	Discontinued
0.754	Intermediate Similarity	NPD8151	Discontinued
0.7517	Intermediate Similarity	NPD1203	Approved
0.7515	Intermediate Similarity	NPD3787	Discontinued
0.7485	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD6190	Approved
0.7483	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD1610	Phase 2
0.7483	Intermediate Similarity	NPD6832	Phase 2
0.7471	Intermediate Similarity	NPD3926	Phase 2
0.7468	Intermediate Similarity	NPD230	Phase 1
0.7459	Intermediate Similarity	NPD7697	Approved
0.7459	Intermediate Similarity	NPD7698	Approved
0.7459	Intermediate Similarity	NPD7696	Phase 3
0.7453	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7452	Intermediate Similarity	NPD2346	Discontinued
0.7448	Intermediate Similarity	NPD1548	Phase 1
0.7423	Intermediate Similarity	NPD1653	Approved
0.7419	Intermediate Similarity	NPD7871	Phase 2
0.7419	Intermediate Similarity	NPD7870	Phase 2
0.7417	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7412	Intermediate Similarity	NPD5711	Approved
0.7412	Intermediate Similarity	NPD5710	Approved
0.7405	Intermediate Similarity	NPD2424	Discontinued
0.7405	Intermediate Similarity	NPD6823	Phase 2
0.7403	Intermediate Similarity	NPD6535	Approved
0.7403	Intermediate Similarity	NPD6534	Approved
0.7401	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD7585	Approved
0.7394	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD7701	Phase 2
0.7391	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7389	Intermediate Similarity	NPD6099	Approved
0.7389	Intermediate Similarity	NPD6100	Approved
0.7375	Intermediate Similarity	NPD2309	Approved
0.7371	Intermediate Similarity	NPD7685	Pre-registration
0.7363	Intermediate Similarity	NPD4361	Phase 2
0.7363	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.736	Intermediate Similarity	NPD8434	Phase 2
0.7358	Intermediate Similarity	NPD1652	Phase 2
0.7349	Intermediate Similarity	NPD6844	Discontinued
0.7349	Intermediate Similarity	NPD37	Approved
0.7341	Intermediate Similarity	NPD7228	Approved
0.734	Intermediate Similarity	NPD7583	Approved
0.7337	Intermediate Similarity	NPD6234	Discontinued
0.7326	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7325	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7321	Intermediate Similarity	NPD4966	Approved
0.7321	Intermediate Similarity	NPD4965	Approved
0.7321	Intermediate Similarity	NPD4967	Phase 2
0.7316	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7316	Intermediate Similarity	NPD7874	Approved
0.7314	Intermediate Similarity	NPD3823	Discontinued
0.7312	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7283	Intermediate Similarity	NPD7699	Phase 2
0.7283	Intermediate Similarity	NPD7700	Phase 2
0.7278	Intermediate Similarity	NPD5406	Approved
0.7278	Intermediate Similarity	NPD5404	Approved
0.7278	Intermediate Similarity	NPD5405	Approved
0.7278	Intermediate Similarity	NPD5408	Approved
0.7277	Intermediate Similarity	NPD7801	Approved
0.7273	Intermediate Similarity	NPD3268	Approved
0.7273	Intermediate Similarity	NPD6798	Discontinued
0.7262	Intermediate Similarity	NPD4288	Approved
0.7251	Intermediate Similarity	NPD7199	Phase 2
0.725	Intermediate Similarity	NPD2654	Approved
0.7244	Intermediate Similarity	NPD1933	Approved
0.7239	Intermediate Similarity	NPD4661	Approved
0.7239	Intermediate Similarity	NPD4662	Approved
0.7219	Intermediate Similarity	NPD3225	Approved
0.7215	Intermediate Similarity	NPD4308	Phase 3
0.7211	Intermediate Similarity	NPD9545	Approved
0.7205	Intermediate Similarity	NPD7003	Approved
0.72	Intermediate Similarity	NPD9717	Approved
0.72	Intermediate Similarity	NPD3972	Approved
0.7188	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD7783	Phase 2
0.7186	Intermediate Similarity	NPD5890	Approved
0.7186	Intermediate Similarity	NPD5889	Approved
0.7178	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7171	Intermediate Similarity	NPD1470	Approved
0.7171	Intermediate Similarity	NPD1164	Approved
0.7171	Intermediate Similarity	NPD2797	Approved
0.7161	Intermediate Similarity	NPD3764	Approved
0.716	Intermediate Similarity	NPD3295	Clinical (unspecified phase)
0.7159	Intermediate Similarity	NPD1729	Discontinued
0.7158	Intermediate Similarity	NPD6213	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