NPASS Compound

Structure

CID323593 OpenBabel06191716172D 32 35 0 0 1 0 0 0 0 0999 V2000 -7.7942 -0.5000 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 -8.6603 -0.0000 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 -2.5981 -1.5000 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 0.0000 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 -8.6603 1.0000 0.0000 C 0 0 0 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 -3.4641 -2.0000 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 -0.5000 0.0000 C 0 0 2 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 2 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 0.0000 -2.0000 0.0000 C 0 0 1 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 -0.8660 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.0622 -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 3 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 -9.5263 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -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 -5.1962 -3.0000 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 -6.9282 -2.0000 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 -1.7321 -0.0000 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 -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 10 2 0 0 0 0 5 11 1 0 0 0 0 6 10 1 0 0 0 0 6 12 2 0 0 0 0 7 22 1 0 0 0 0 8 20 1 0 0 0 0 9 23 1 0 0 0 0 10 30 1 0 0 0 0 11 14 2 0 0 0 0 11 24 1 0 0 0 0 12 14 1 0 0 0 0 12 31 1 0 0 0 0 13 7 1 6 0 0 0 13 15 1 0 0 0 0 13 32 1 0 0 0 0 14 16 1 0 0 0 0 15 17 1 0 0 0 0 15 25 1 1 0 0 0 16 18 1 0 0 0 0 16 26 2 0 0 0 0 17 19 1 0 0 0 0 17 27 1 6 0 0 0 18 20 2 0 0 0 0 18 28 1 0 0 0 0 19 21 1 0 0 0 0 19 29 1 1 0 0 0 20 31 1 0 0 0 0 21 30 1 0 0 0 0 21 32 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	448.1
Volume:	413.147
LogP:	0.587
LogD:	0.248
LogS:	-3.65
# Rotatable Bonds:	4
TPSA:	190.28
# H-Bond Aceptor:	11
# H-Bond Donor:	7
# Rings:	4
# Heavy Atoms:	11

MedChem Properties

QED Drug-Likeness Score:	0.279
Synthetic Accessibility Score:	3.894
Fsp3:	0.286
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.202
MDCK Permeability:	7.747678864689078e-06
Pgp-inhibitor:	0.009
Pgp-substrate:	0.371
Human Intestinal Absorption (HIA):	0.595
20% Bioavailability (F20%):	0.034
30% Bioavailability (F30%):	0.997

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.024
Plasma Protein Binding (PPB):	92.08472442626953%
Volume Distribution (VD):	0.809
Pgp-substrate:	8.014492988586426%

ADMET: Metabolism

CYP1A2-inhibitor:	0.174
CYP1A2-substrate:	0.034
CYP2C19-inhibitor:	0.023
CYP2C19-substrate:	0.052
CYP2C9-inhibitor:	0.038
CYP2C9-substrate:	0.186
CYP2D6-inhibitor:	0.223
CYP2D6-substrate:	0.159
CYP3A4-inhibitor:	0.069
CYP3A4-substrate:	0.018

ADMET: Excretion

Clearance (CL):	2.914
Half-life (T1/2):	0.878

ADMET: Toxicity

hERG Blockers:	0.149
Human Hepatotoxicity (H-HT):	0.09
Drug-inuced Liver Injury (DILI):	0.98
AMES Toxicity:	0.82
Rat Oral Acute Toxicity:	0.048
Maximum Recommended Daily Dose:	0.003
Skin Sensitization:	0.251
Carcinogencity:	0.27
Eye Corrosion:	0.003
Eye Irritation:	0.132
Respiratory Toxicity:	0.028

Download Data

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

Natural Product: NPC323593

Natural Product ID:	NPC323593
*Common Name:**	3,5-Dihydroxy-2-(4-Hydroxy-Phenyl)-7-(3,4,5-Trihydroxy-6-Hydroxymethyl-Tetrahydro-Pyran-2-Yloxy)-Chromen-4-One
IUPAC Name:	3,5-dihydroxy-2-(4-hydroxyphenyl)-7-[(3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-4-one
Synonyms:
Standard InCHIKey:	YPWHZCPMOQGCDQ-CXWQUDHASA-N
Standard InCHI:	InChI=1S/C21H20O11/c22-7-13-15(25)17(27)19(29)21(32-13)30-10-5-11(24)14-12(6-10)31-20(18(28)16(14)26)8-1-3-9(23)4-2-8/h1-6,13,15,17,19,21-25,27-29H,7H2/t13-,15-,17+,19-,21?/m1/s1
SMILES:	OC[C@H]1OC(Oc2cc(O)c3c(c2)oc(c(c3=O)O)c2ccc(cc2)O)[C@@H]([C@H]([C@@H]1O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1159471
PubChem CID:	10275538
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001111] Flavonoid glycosides [CHEMONTID:0001583] Flavonoid O-glycosides [CHEMONTID:0003533] Flavonoid-7-O-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
NPO9646	Crotalaria pallida	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12662101]
NPO9646	Crotalaria pallida	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15013012]
NPO10262	Crotalaria assamica	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15013012]
NPO13353	Sedum sarmentosum	Species	Crassulaceae	Eukaryota	n.a.	aerial part	n.a.	PMID[15577228]
NPO13353	Sedum sarmentosum	Species	Crassulaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22085682]
NPO13353	Sedum sarmentosum	Species	Crassulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO10262	Crotalaria assamica	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO13353	Sedum sarmentosum	Species	Crassulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9646	Crotalaria pallida	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10262	Crotalaria assamica	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13353	Sedum sarmentosum	Species	Crassulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO13353	Sedum sarmentosum	Species	Crassulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO13353	Sedum sarmentosum	Species	Crassulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9646	Crotalaria pallida	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10262	Crotalaria assamica	Species	Fabaceae	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	6

Activity Type	# Activity
Individual Protein	2
Organism	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT3102	Individual Protein	Beta-glucuronidase	Rattus norvegicus	IC50	>	30000.0	nM	PMID[506400]
NPT3103	Individual Protein	Lysozyme C	Rattus norvegicus	IC50	>	30000.0	nM	PMID[506400]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	IC50	>	30000.0	nM	PMID[506400]
NPT32	Organism	Mus musculus	Mus musculus	IC50	>	30000.0	nM	PMID[506400]

☑ 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 NPC323593 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	436
0.1-0.2	1771
0.2-0.3	4327
0.3-0.4	10016
0.4-0.5	8261
0.5-0.6	4375
0.6-0.7	5600
0.7-0.8	4742
0.8-0.85	1903
0.85-0.9	767
0.9-0.95	383
0.95-1	116

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC203500
1.0	High Similarity	NPC307938
0.9933	High Similarity	NPC108831
0.9933	High Similarity	NPC54802
0.9933	High Similarity	NPC77672
0.9933	High Similarity	NPC135391
0.9933	High Similarity	NPC78263
0.9933	High Similarity	NPC197304
0.9933	High Similarity	NPC182634
0.9933	High Similarity	NPC133671
0.9867	High Similarity	NPC41121
0.9867	High Similarity	NPC320283
0.9867	High Similarity	NPC472459
0.9867	High Similarity	NPC111929
0.9865	High Similarity	NPC210003
0.9865	High Similarity	NPC39360
0.9865	High Similarity	NPC83283
0.9865	High Similarity	NPC29763
0.9865	High Similarity	NPC143851
0.9801	High Similarity	NPC471079
0.9801	High Similarity	NPC304741
0.9801	High Similarity	NPC470405
0.9801	High Similarity	NPC136761
0.9801	High Similarity	NPC187379
0.9799	High Similarity	NPC95090
0.9799	High Similarity	NPC27408
0.9737	High Similarity	NPC159579
0.9737	High Similarity	NPC253788
0.9737	High Similarity	NPC215710
0.9737	High Similarity	NPC170052
0.9737	High Similarity	NPC64305
0.9737	High Similarity	NPC276377
0.9737	High Similarity	NPC470125
0.9737	High Similarity	NPC297987
0.9737	High Similarity	NPC265885
0.9737	High Similarity	NPC249281
0.9737	High Similarity	NPC48093
0.9737	High Similarity	NPC259957
0.9737	High Similarity	NPC163242
0.9737	High Similarity	NPC129217
0.9737	High Similarity	NPC116458
0.9737	High Similarity	NPC181465
0.9737	High Similarity	NPC282169
0.9737	High Similarity	NPC85707
0.9737	High Similarity	NPC246943
0.9737	High Similarity	NPC476215
0.9737	High Similarity	NPC224530
0.9737	High Similarity	NPC135846
0.9737	High Similarity	NPC173582
0.9737	High Similarity	NPC473438
0.9737	High Similarity	NPC216496
0.9737	High Similarity	NPC139320
0.9673	High Similarity	NPC150164
0.9673	High Similarity	NPC131745
0.9673	High Similarity	NPC27942
0.9673	High Similarity	NPC240306
0.9671	High Similarity	NPC153342
0.9669	High Similarity	NPC156457
0.9669	High Similarity	NPC122809
0.9669	High Similarity	NPC65003
0.9669	High Similarity	NPC44931
0.9669	High Similarity	NPC129827
0.9669	High Similarity	NPC313163
0.9669	High Similarity	NPC288084
0.9669	High Similarity	NPC473512
0.9669	High Similarity	NPC197896
0.9669	High Similarity	NPC60966
0.9669	High Similarity	NPC6985
0.9669	High Similarity	NPC161749
0.9669	High Similarity	NPC258035
0.9667	High Similarity	NPC97052
0.9667	High Similarity	NPC72649
0.9667	High Similarity	NPC169248
0.9667	High Similarity	NPC26195
0.9667	High Similarity	NPC39351
0.9664	High Similarity	NPC259767
0.9664	High Similarity	NPC259182
0.9664	High Similarity	NPC121001
0.9664	High Similarity	NPC88484
0.961	High Similarity	NPC121703
0.961	High Similarity	NPC66087
0.961	High Similarity	NPC183672
0.961	High Similarity	NPC179198
0.961	High Similarity	NPC80068
0.961	High Similarity	NPC278419
0.9605	High Similarity	NPC22062
0.9605	High Similarity	NPC73511
0.9605	High Similarity	NPC104677
0.9605	High Similarity	NPC138811
0.9605	High Similarity	NPC473634
0.9603	High Similarity	NPC170475
0.9603	High Similarity	NPC261866
0.9603	High Similarity	NPC206378
0.96	High Similarity	NPC106625
0.9548	High Similarity	NPC292929
0.9548	High Similarity	NPC139060
0.9548	High Similarity	NPC129264
0.9548	High Similarity	NPC85751
0.9548	High Similarity	NPC277205
0.9548	High Similarity	NPC289667
0.9548	High Similarity	NPC205824
0.9548	High Similarity	NPC135358
0.9548	High Similarity	NPC76831
0.9548	High Similarity	NPC19240
0.9548	High Similarity	NPC72016
0.9548	High Similarity	NPC287889
0.9545	High Similarity	NPC259834
0.9542	High Similarity	NPC473623
0.9536	High Similarity	NPC99233
0.953	High Similarity	NPC191154
0.9487	High Similarity	NPC11432
0.9487	High Similarity	NPC64425
0.9487	High Similarity	NPC281131
0.9487	High Similarity	NPC32641
0.9487	High Similarity	NPC276222
0.9487	High Similarity	NPC476470
0.9487	High Similarity	NPC179950
0.9487	High Similarity	NPC186816
0.9487	High Similarity	NPC189564
0.9487	High Similarity	NPC308404
0.9487	High Similarity	NPC12013
0.9487	High Similarity	NPC253662
0.9487	High Similarity	NPC56077
0.9487	High Similarity	NPC221342
0.9487	High Similarity	NPC274618
0.9487	High Similarity	NPC142142
0.9487	High Similarity	NPC88789
0.9487	High Similarity	NPC21100
0.9487	High Similarity	NPC197285
0.9487	High Similarity	NPC203145
0.9487	High Similarity	NPC256188
0.9487	High Similarity	NPC477613
0.9487	High Similarity	NPC145038
0.9487	High Similarity	NPC118284
0.9481	High Similarity	NPC303913
0.9481	High Similarity	NPC101636
0.9481	High Similarity	NPC195685
0.9481	High Similarity	NPC477629
0.9481	High Similarity	NPC270675
0.9481	High Similarity	NPC477628
0.9481	High Similarity	NPC210961
0.9481	High Similarity	NPC47923
0.9481	High Similarity	NPC472994
0.9477	High Similarity	NPC308265
0.9474	High Similarity	NPC295613
0.9474	High Similarity	NPC45165
0.9474	High Similarity	NPC473657
0.9474	High Similarity	NPC149368
0.9474	High Similarity	NPC127406
0.9474	High Similarity	NPC265480
0.9467	High Similarity	NPC134819
0.9427	High Similarity	NPC52550
0.9427	High Similarity	NPC317489
0.9427	High Similarity	NPC84362
0.9427	High Similarity	NPC223424
0.9427	High Similarity	NPC127546
0.9427	High Similarity	NPC173637
0.9423	High Similarity	NPC19388
0.9423	High Similarity	NPC55786
0.9423	High Similarity	NPC240431
0.9419	High Similarity	NPC244875
0.9419	High Similarity	NPC189142
0.9419	High Similarity	NPC77660
0.9419	High Similarity	NPC475382
0.9419	High Similarity	NPC44947
0.9419	High Similarity	NPC298171
0.9416	High Similarity	NPC271270
0.9416	High Similarity	NPC271479
0.9416	High Similarity	NPC97285
0.9416	High Similarity	NPC246469
0.9416	High Similarity	NPC142860
0.9416	High Similarity	NPC472320
0.9416	High Similarity	NPC200708
0.9412	High Similarity	NPC43638
0.9412	High Similarity	NPC23817
0.9396	High Similarity	NPC199335
0.9367	High Similarity	NPC120099
0.9367	High Similarity	NPC223747
0.9367	High Similarity	NPC203050
0.9367	High Similarity	NPC219904
0.9367	High Similarity	NPC5319
0.9367	High Similarity	NPC225434
0.9363	High Similarity	NPC277174
0.9363	High Similarity	NPC73855
0.9363	High Similarity	NPC328940
0.9363	High Similarity	NPC135599
0.9363	High Similarity	NPC113968
0.9359	High Similarity	NPC473644
0.9359	High Similarity	NPC311850
0.9359	High Similarity	NPC243930
0.9359	High Similarity	NPC168822
0.9359	High Similarity	NPC88023
0.9359	High Similarity	NPC19709
0.9359	High Similarity	NPC257566
0.9359	High Similarity	NPC270335
0.9359	High Similarity	NPC124155
0.9359	High Similarity	NPC191306
0.9359	High Similarity	NPC309025
0.9351	High Similarity	NPC43761
0.9342	High Similarity	NPC268950

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 NPC323593 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	395
0.1-0.2	927
0.2-0.3	1878
0.3-0.4	2746
0.4-0.5	1847
0.5-0.6	932
0.6-0.7	261
0.7-0.8	120
0.8-0.85	21
0.85-0.9	15
0.9-0.95	8
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9669	High Similarity	NPD4381	Clinical (unspecified phase)
0.9367	High Similarity	NPD7804	Clinical (unspecified phase)
0.925	High Similarity	NPD6797	Phase 2
0.9193	High Similarity	NPD7251	Discontinued
0.9136	High Similarity	NPD7808	Phase 3
0.9136	High Similarity	NPD4338	Clinical (unspecified phase)
0.9125	High Similarity	NPD7054	Approved
0.9068	High Similarity	NPD7472	Approved
0.902	High Similarity	NPD4380	Phase 2
0.8951	High Similarity	NPD7074	Phase 3
0.8944	High Similarity	NPD3818	Discontinued
0.8824	High Similarity	NPD5403	Approved
0.8797	High Similarity	NPD7075	Discontinued
0.8782	High Similarity	NPD6801	Discontinued
0.8725	High Similarity	NPD1552	Clinical (unspecified phase)
0.8725	High Similarity	NPD1550	Clinical (unspecified phase)
0.8704	High Similarity	NPD6167	Clinical (unspecified phase)
0.8704	High Similarity	NPD6166	Phase 2
0.8704	High Similarity	NPD6168	Clinical (unspecified phase)
0.8693	High Similarity	NPD4378	Clinical (unspecified phase)
0.8693	High Similarity	NPD5401	Approved
0.8667	High Similarity	NPD1549	Phase 2
0.8627	High Similarity	NPD6799	Approved
0.8608	High Similarity	NPD7096	Clinical (unspecified phase)
0.8553	High Similarity	NPD3817	Phase 2
0.8553	High Similarity	NPD5402	Approved
0.8544	High Similarity	NPD1934	Approved
0.8516	High Similarity	NPD1512	Approved
0.8503	High Similarity	NPD6559	Discontinued
0.8491	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8387	Intermediate Similarity	NPD1511	Approved
0.8375	Intermediate Similarity	NPD2801	Approved
0.8365	Intermediate Similarity	NPD7411	Suspended
0.8344	Intermediate Similarity	NPD1510	Phase 2
0.8333	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8323	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8302	Intermediate Similarity	NPD6599	Discontinued
0.8289	Intermediate Similarity	NPD2796	Approved
0.8272	Intermediate Similarity	NPD3882	Suspended
0.8272	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8118	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8079	Intermediate Similarity	NPD1240	Approved
0.8068	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.8047	Intermediate Similarity	NPD3751	Discontinued
0.8037	Intermediate Similarity	NPD7819	Suspended
0.8024	Intermediate Similarity	NPD3787	Discontinued
0.7974	Intermediate Similarity	NPD1607	Approved
0.7964	Intermediate Similarity	NPD6959	Discontinued
0.7962	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7962	Intermediate Similarity	NPD3750	Approved
0.7929	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7892	Intermediate Similarity	NPD7584	Approved
0.7874	Intermediate Similarity	NPD8313	Approved
0.7874	Intermediate Similarity	NPD8312	Approved
0.784	Intermediate Similarity	NPD1653	Approved
0.7829	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7821	Intermediate Similarity	NPD1551	Phase 2
0.7818	Intermediate Similarity	NPD8455	Phase 2
0.7798	Intermediate Similarity	NPD5494	Approved
0.779	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7784	Intermediate Similarity	NPD3749	Approved
0.776	Intermediate Similarity	NPD6780	Approved
0.776	Intermediate Similarity	NPD6776	Approved
0.776	Intermediate Similarity	NPD6779	Approved
0.776	Intermediate Similarity	NPD6781	Approved
0.776	Intermediate Similarity	NPD6778	Approved
0.776	Intermediate Similarity	NPD6782	Approved
0.776	Intermediate Similarity	NPD6777	Approved
0.7736	Intermediate Similarity	NPD4628	Phase 3
0.7725	Intermediate Similarity	NPD7768	Phase 2
0.7722	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7703	Intermediate Similarity	NPD1091	Approved
0.7688	Intermediate Similarity	NPD5844	Phase 1
0.7673	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7643	Intermediate Similarity	NPD3748	Approved
0.7634	Intermediate Similarity	NPD7435	Discontinued
0.7605	Intermediate Similarity	NPD1465	Phase 2
0.7602	Intermediate Similarity	NPD6232	Discontinued
0.7572	Intermediate Similarity	NPD7473	Discontinued
0.7564	Intermediate Similarity	NPD1933	Approved
0.7561	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7558	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7557	Intermediate Similarity	NPD7685	Pre-registration
0.7544	Intermediate Similarity	NPD7199	Phase 2
0.754	Intermediate Similarity	NPD7698	Approved
0.754	Intermediate Similarity	NPD7696	Phase 3
0.754	Intermediate Similarity	NPD7697	Approved
0.7532	Intermediate Similarity	NPD7033	Discontinued
0.7514	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1203	Approved
0.75	Intermediate Similarity	NPD7870	Phase 2
0.75	Intermediate Similarity	NPD7871	Phase 2
0.75	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1613	Approved
0.7486	Intermediate Similarity	NPD6534	Approved
0.7486	Intermediate Similarity	NPD6535	Approved
0.7484	Intermediate Similarity	NPD6798	Discontinued
0.7474	Intermediate Similarity	NPD7701	Phase 2
0.7474	Intermediate Similarity	NPD7585	Approved
0.7468	Intermediate Similarity	NPD6832	Phase 2
0.7467	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7455	Intermediate Similarity	NPD920	Approved
0.7453	Intermediate Similarity	NPD2800	Approved
0.7453	Intermediate Similarity	NPD1652	Phase 2
0.7439	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7436	Intermediate Similarity	NPD6233	Phase 2
0.7435	Intermediate Similarity	NPD8151	Discontinued
0.7432	Intermediate Similarity	NPD1548	Phase 1
0.7429	Intermediate Similarity	NPD7228	Approved
0.7427	Intermediate Similarity	NPD919	Approved
0.7423	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7421	Intermediate Similarity	NPD7583	Approved
0.7416	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7405	Intermediate Similarity	NPD6651	Approved
0.7401	Intermediate Similarity	NPD5953	Discontinued
0.7396	Intermediate Similarity	NPD7874	Approved
0.7396	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD4360	Phase 2
0.7391	Intermediate Similarity	NPD4363	Phase 3
0.7389	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD7286	Phase 2
0.7375	Intermediate Similarity	NPD2935	Discontinued
0.7372	Intermediate Similarity	NPD2313	Discontinued
0.7366	Intermediate Similarity	NPD7699	Phase 2
0.7366	Intermediate Similarity	NPD7700	Phase 2
0.7365	Intermediate Similarity	NPD7458	Discontinued
0.7362	Intermediate Similarity	NPD6190	Approved
0.7358	Intermediate Similarity	NPD7783	Phase 2
0.7358	Intermediate Similarity	NPD7801	Approved
0.7358	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7356	Intermediate Similarity	NPD3926	Phase 2
0.7355	Intermediate Similarity	NPD4908	Phase 1
0.7346	Intermediate Similarity	NPD1243	Approved
0.7342	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7342	Intermediate Similarity	NPD5124	Phase 1
0.7341	Intermediate Similarity	NPD1247	Approved
0.7338	Intermediate Similarity	NPD2798	Approved
0.7337	Intermediate Similarity	NPD37	Approved
0.7333	Intermediate Similarity	NPD2532	Approved
0.7333	Intermediate Similarity	NPD2534	Approved
0.7333	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD2533	Approved
0.7329	Intermediate Similarity	NPD7266	Discontinued
0.7326	Intermediate Similarity	NPD6234	Discontinued
0.732	Intermediate Similarity	NPD3225	Approved
0.731	Intermediate Similarity	NPD4966	Approved
0.731	Intermediate Similarity	NPD4967	Phase 2
0.731	Intermediate Similarity	NPD4965	Approved
0.7302	Intermediate Similarity	NPD6823	Phase 2
0.7278	Intermediate Similarity	NPD943	Approved
0.7273	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7268	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7261	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7261	Intermediate Similarity	NPD3268	Approved
0.7253	Intermediate Similarity	NPD8434	Phase 2
0.7244	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7237	Intermediate Similarity	NPD1610	Phase 2
0.7237	Intermediate Similarity	NPD422	Phase 1
0.7233	Intermediate Similarity	NPD6355	Discontinued
0.7225	Intermediate Similarity	NPD8319	Approved
0.7225	Intermediate Similarity	NPD8320	Phase 1
0.7222	Intermediate Similarity	NPD2344	Approved
0.7205	Intermediate Similarity	NPD2799	Discontinued
0.719	Intermediate Similarity	NPD9717	Approved
0.7179	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7161	Intermediate Similarity	NPD2797	Approved
0.716	Intermediate Similarity	NPD6099	Approved
0.716	Intermediate Similarity	NPD6100	Approved
0.716	Intermediate Similarity	NPD3226	Approved
0.7158	Intermediate Similarity	NPD8150	Discontinued
0.7135	Intermediate Similarity	NPD6844	Discontinued
0.7125	Intermediate Similarity	NPD230	Phase 1
0.7125	Intermediate Similarity	NPD4340	Discontinued
0.7107	Intermediate Similarity	NPD4062	Phase 3
0.7099	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD3027	Phase 3
0.7072	Intermediate Similarity	NPD7240	Approved
0.7066	Intermediate Similarity	NPD7390	Discontinued
0.7059	Intermediate Similarity	NPD6213	Phase 3
0.7059	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD6212	Phase 3
0.7052	Intermediate Similarity	NPD4288	Approved
0.7048	Intermediate Similarity	NPD3887	Approved
0.7048	Intermediate Similarity	NPD2309	Approved
0.7048	Intermediate Similarity	NPD2354	Approved
0.7037	Intermediate Similarity	NPD7097	Phase 1
0.703	Intermediate Similarity	NPD2654	Approved
0.703	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.7024	Intermediate Similarity	NPD4661	Approved
0.7024	Intermediate Similarity	NPD4662	Approved
0.7019	Intermediate Similarity	NPD447	Suspended
0.7019	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7012	Intermediate Similarity	NPD2346	Discontinued
0.6994	Remote Similarity	NPD4308	Phase 3
0.6988	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6984	Remote Similarity	NPD4361	Phase 2
0.6984	Remote Similarity	NPD4362	Clinical (unspecified phase)
0.6974	Remote Similarity	NPD9545	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