NPASS Compound

Structure

CID153342 OpenBabel06191715522D 31 34 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 -1.7321 3.0000 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 -1.7321 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 -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 1 0 0 0 0 0 0 0 0 0 -2.5981 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -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 -2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7321 -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 2 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 1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5981 5.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -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 2.5981 -0.5000 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 2.5981 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 2.5000 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 -3.4641 1.0000 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 4 1 0 0 0 0 2 9 2 0 0 0 0 3 5 2 0 0 0 0 3 9 1 0 0 0 0 4 10 2 0 0 0 0 5 10 1 0 0 0 0 6 11 2 0 0 0 0 6 12 1 0 0 0 0 7 11 1 0 0 0 0 7 13 2 0 0 0 0 8 1 1 6 0 0 0 8 15 1 0 0 0 0 8 29 1 0 0 0 0 10 22 1 0 0 0 0 11 23 1 0 0 0 0 12 14 2 0 0 0 0 12 24 1 0 0 0 0 13 14 1 0 0 0 0 13 30 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 20 1 0 0 0 0 16 26 2 0 0 0 0 17 18 1 0 0 0 0 17 27 1 6 0 0 0 18 21 1 0 0 0 0 18 28 1 6 0 0 0 19 9 1 1 0 0 0 19 20 1 0 0 0 0 19 30 1 0 0 0 0 20 31 1 6 0 0 0 21 29 1 0 0 0 0 21 31 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	434.12
Volume:	406.993
LogP:	1.281
LogD:	0.877
LogS:	-4.157
# Rotatable Bonds:	3
TPSA:	166.14
# H-Bond Aceptor:	10
# H-Bond Donor:	6
# Rings:	4
# Heavy Atoms:	10

MedChem Properties

QED Drug-Likeness Score:	0.396
Synthetic Accessibility Score:	4.235
Fsp3:	0.381
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.532
MDCK Permeability:	7.756922059343196e-06
Pgp-inhibitor:	0.021
Pgp-substrate:	0.918
Human Intestinal Absorption (HIA):	0.252
20% Bioavailability (F20%):	0.007
30% Bioavailability (F30%):	0.997

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.036
Plasma Protein Binding (PPB):	91.6500015258789%
Volume Distribution (VD):	0.648
Pgp-substrate:	10.022496223449707%

ADMET: Metabolism

CYP1A2-inhibitor:	0.095
CYP1A2-substrate:	0.07
CYP2C19-inhibitor:	0.062
CYP2C19-substrate:	0.06
CYP2C9-inhibitor:	0.101
CYP2C9-substrate:	0.839
CYP2D6-inhibitor:	0.39
CYP2D6-substrate:	0.229
CYP3A4-inhibitor:	0.55
CYP3A4-substrate:	0.117

ADMET: Excretion

Clearance (CL):	4.271
Half-life (T1/2):	0.49

ADMET: Toxicity

hERG Blockers:	0.017
Human Hepatotoxicity (H-HT):	0.146
Drug-inuced Liver Injury (DILI):	0.96
AMES Toxicity:	0.555
Rat Oral Acute Toxicity:	0.064
Maximum Recommended Daily Dose:	0.012
Skin Sensitization:	0.902
Carcinogencity:	0.266
Eye Corrosion:	0.003
Eye Irritation:	0.688
Respiratory Toxicity:	0.059

Download Data

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

Natural Product: NPC153342

Natural Product ID:	NPC153342
*Common Name:**	Catechin-3-O-Alpha-L-Rhamnopyranoside
IUPAC Name:	(2S,3S)-5,7-dihydroxy-2-(4-hydroxyphenyl)-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy-2,3-dihydrochromen-4-one
Synonyms:
Standard InCHIKey:	VQUPQWGKORWZII-ZUSBORFQSA-N
Standard InCHI:	InChI=1S/C21H22O10/c1-8-15(25)17(27)18(28)21(29-8)31-20-16(26)14-12(24)6-11(23)7-13(14)30-19(20)9-2-4-10(22)5-3-9/h2-8,15,17-25,27-28H,1H3/t8-,15-,17+,18+,19-,20+,21-/m0/s1
SMILES:	C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)O[C@@H]1C(=O)c2c(cc(cc2O[C@H]1c1ccc(cc1)O)O)O)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3109441
PubChem CID:	76310272
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001111] Flavonoid glycosides [CHEMONTID:0001583] Flavonoid O-glycosides [CHEMONTID:0003531] Flavonoid-3-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
NPO25611	Smilax china	Species	Smilacaceae	Eukaryota	stems	n.a.	n.a.	PMID[16252910]
NPO33509	byrsonima coccolobifolia	Species	Malpighiaceae	Eukaryota	leaves and stems	cerrado at the Federal University of So Carlos (UFSCar), So Carlos, SP, Brazil	2011-Jul	PMID[24521209]
NPO7132	Smilax glabra	Species	Smilacaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO25611	Smilax china	Species	Smilacaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO25611	Smilax china	Species	Smilacaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7132	Smilax glabra	Species	Smilacaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25611	Smilax china	Species	Smilacaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO7132	Smilax glabra	Species	Smilacaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO7132	Smilax glabra	Species	Smilacaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO25611	Smilax china	Species	Smilacaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO25611	Smilax china	Species	Smilacaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7132	Smilax glabra	Species	Smilacaceae	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

Activity Type	# Activity
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1662	Individual Protein	Arginase	Leishmania amazonensis	IC50	=	35100.0	nM	PMID[536543]

☑ 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 NPC153342 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	378
0.1-0.2	1519
0.2-0.3	3660
0.3-0.4	9031
0.4-0.5	9308
0.5-0.6	4480
0.6-0.7	5579
0.7-0.8	5777
0.8-0.85	1953
0.85-0.9	807
0.9-0.95	185
0.95-1	20

Similarity Score	Similarity Level	Natural Product ID
0.9804	High Similarity	NPC181465
0.9804	High Similarity	NPC473438
0.9804	High Similarity	NPC249281
0.9804	High Similarity	NPC265885
0.9804	High Similarity	NPC163242
0.9804	High Similarity	NPC116458
0.9804	High Similarity	NPC246943
0.9804	High Similarity	NPC276377
0.9804	High Similarity	NPC173582
0.9804	High Similarity	NPC139320
0.9804	High Similarity	NPC253788
0.9804	High Similarity	NPC476215
0.9804	High Similarity	NPC215710
0.9803	High Similarity	NPC111929
0.9803	High Similarity	NPC41121
0.9803	High Similarity	NPC320283
0.9803	High Similarity	NPC472459
0.9801	High Similarity	NPC206378
0.974	High Similarity	NPC259834
0.974	High Similarity	NPC240306
0.9739	High Similarity	NPC304741
0.9739	High Similarity	NPC187379
0.9739	High Similarity	NPC471079
0.9739	High Similarity	NPC470405
0.9737	High Similarity	NPC77672
0.9737	High Similarity	NPC6985
0.9737	High Similarity	NPC108831
0.9737	High Similarity	NPC182634
0.9737	High Similarity	NPC54802
0.9737	High Similarity	NPC133671
0.9737	High Similarity	NPC78263
0.9737	High Similarity	NPC135391
0.9737	High Similarity	NPC197304
0.9735	High Similarity	NPC39351
0.9735	High Similarity	NPC26195
0.9735	High Similarity	NPC169248
0.9735	High Similarity	NPC72649
0.9735	High Similarity	NPC97052
0.9677	High Similarity	NPC66087
0.9677	High Similarity	NPC278419
0.9677	High Similarity	NPC179198
0.9675	High Similarity	NPC170052
0.9675	High Similarity	NPC297987
0.9675	High Similarity	NPC135846
0.9675	High Similarity	NPC48093
0.9675	High Similarity	NPC129217
0.9675	High Similarity	NPC216496
0.9675	High Similarity	NPC224530
0.9675	High Similarity	NPC259957
0.9675	High Similarity	NPC64305
0.9675	High Similarity	NPC85707
0.9675	High Similarity	NPC159579
0.9671	High Similarity	NPC323593
0.9671	High Similarity	NPC170475
0.9671	High Similarity	NPC203500
0.9671	High Similarity	NPC307938
0.9669	High Similarity	NPC106625
0.9613	High Similarity	NPC150164
0.9613	High Similarity	NPC131745
0.9613	High Similarity	NPC27942
0.961	High Similarity	NPC97285
0.961	High Similarity	NPC142860
0.961	High Similarity	NPC271270
0.961	High Similarity	NPC246469
0.961	High Similarity	NPC136761
0.9608	High Similarity	NPC65003
0.9608	High Similarity	NPC44931
0.9608	High Similarity	NPC473512
0.9608	High Similarity	NPC129827
0.9605	High Similarity	NPC95090
0.9605	High Similarity	NPC99233
0.9605	High Similarity	NPC27408
0.9603	High Similarity	NPC121001
0.9603	High Similarity	NPC259182
0.9557	High Similarity	NPC270578
0.9557	High Similarity	NPC5319
0.9557	High Similarity	NPC52382
0.9554	High Similarity	NPC64425
0.9554	High Similarity	NPC476470
0.9554	High Similarity	NPC32641
0.9554	High Similarity	NPC256188
0.9554	High Similarity	NPC142142
0.9554	High Similarity	NPC11432
0.9554	High Similarity	NPC189564
0.9554	High Similarity	NPC12013
0.9554	High Similarity	NPC477613
0.9554	High Similarity	NPC186816
0.9554	High Similarity	NPC203145
0.9554	High Similarity	NPC221342
0.9551	High Similarity	NPC121703
0.9551	High Similarity	NPC183672
0.9548	High Similarity	NPC470125
0.9548	High Similarity	NPC282169
0.9548	High Similarity	NPC303913
0.9545	High Similarity	NPC473634
0.9545	High Similarity	NPC22062
0.9545	High Similarity	NPC138811
0.9545	High Similarity	NPC308265
0.9545	High Similarity	NPC104677
0.9545	High Similarity	NPC73511
0.9542	High Similarity	NPC127406
0.9539	High Similarity	NPC39360
0.9539	High Similarity	NPC210003
0.9539	High Similarity	NPC83283
0.9539	High Similarity	NPC29763
0.9539	High Similarity	NPC143851
0.9494	High Similarity	NPC160156
0.9494	High Similarity	NPC92565
0.949	High Similarity	NPC72016
0.949	High Similarity	NPC135358
0.949	High Similarity	NPC76831
0.949	High Similarity	NPC287889
0.949	High Similarity	NPC289667
0.949	High Similarity	NPC292929
0.9487	High Similarity	NPC190450
0.9487	High Similarity	NPC44947
0.9484	High Similarity	NPC271479
0.9484	High Similarity	NPC200708
0.9484	High Similarity	NPC472320
0.9484	High Similarity	NPC473623
0.9481	High Similarity	NPC313163
0.9481	High Similarity	NPC161749
0.9481	High Similarity	NPC197896
0.9481	High Similarity	NPC258035
0.9481	High Similarity	NPC288084
0.9481	High Similarity	NPC23817
0.9481	High Similarity	NPC43638
0.9481	High Similarity	NPC156457
0.9481	High Similarity	NPC60966
0.9474	High Similarity	NPC88484
0.9474	High Similarity	NPC259767
0.9427	High Similarity	NPC257566
0.9427	High Similarity	NPC124155
0.9423	High Similarity	NPC101636
0.9423	High Similarity	NPC47923
0.9416	High Similarity	NPC295613
0.9416	High Similarity	NPC473657
0.9416	High Similarity	NPC45165
0.9375	High Similarity	NPC209550
0.9375	High Similarity	NPC277532
0.9375	High Similarity	NPC95866
0.9375	High Similarity	NPC138990
0.9375	High Similarity	NPC175429
0.9371	High Similarity	NPC173637
0.9371	High Similarity	NPC127546
0.9371	High Similarity	NPC52550
0.9371	High Similarity	NPC84362
0.9371	High Similarity	NPC317489
0.9371	High Similarity	NPC223424
0.9367	High Similarity	NPC19240
0.9367	High Similarity	NPC85751
0.9367	High Similarity	NPC139060
0.9367	High Similarity	NPC205824
0.9367	High Similarity	NPC129264
0.9363	High Similarity	NPC298171
0.9363	High Similarity	NPC472876
0.9363	High Similarity	NPC244875
0.9363	High Similarity	NPC475382
0.9355	High Similarity	NPC122809
0.9342	High Similarity	NPC191154
0.9342	High Similarity	NPC477240
0.9342	High Similarity	NPC213723
0.9342	High Similarity	NPC214454
0.9342	High Similarity	NPC106025
0.9338	High Similarity	NPC199335
0.9321	High Similarity	NPC294629
0.9317	High Similarity	NPC176740
0.9317	High Similarity	NPC134532
0.9317	High Similarity	NPC33054
0.9317	High Similarity	NPC155877
0.9317	High Similarity	NPC474522
0.9317	High Similarity	NPC203259
0.9317	High Similarity	NPC471725
0.9317	High Similarity	NPC471748
0.9313	High Similarity	NPC219904
0.9313	High Similarity	NPC225434
0.9313	High Similarity	NPC120099
0.9313	High Similarity	NPC223747
0.9313	High Similarity	NPC203050
0.9308	High Similarity	NPC118284
0.9308	High Similarity	NPC277174
0.9308	High Similarity	NPC70441
0.9308	High Similarity	NPC73855
0.9308	High Similarity	NPC274618
0.9308	High Similarity	NPC135599
0.9308	High Similarity	NPC56077
0.9308	High Similarity	NPC281131
0.9308	High Similarity	NPC308404
0.9308	High Similarity	NPC236934
0.9308	High Similarity	NPC88789
0.9308	High Similarity	NPC5778
0.9308	High Similarity	NPC145038
0.9308	High Similarity	NPC328940
0.9308	High Similarity	NPC253662
0.9308	High Similarity	NPC276222
0.9308	High Similarity	NPC179950
0.9308	High Similarity	NPC113968
0.9304	High Similarity	NPC473644
0.9304	High Similarity	NPC80068
0.9304	High Similarity	NPC29830

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 NPC153342 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	330
0.1-0.2	870
0.2-0.3	1723
0.3-0.4	2665
0.4-0.5	1972
0.5-0.6	1051
0.6-0.7	367
0.7-0.8	131
0.8-0.85	26
0.85-0.9	15
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9557	High Similarity	NPD7804	Clinical (unspecified phase)
0.9481	High Similarity	NPD4381	Clinical (unspecified phase)
0.9317	High Similarity	NPD6797	Phase 2
0.9259	High Similarity	NPD7251	Discontinued
0.9202	High Similarity	NPD7808	Phase 3
0.9136	High Similarity	NPD7074	Phase 3
0.9074	High Similarity	NPD7054	Approved
0.9018	High Similarity	NPD7472	Approved
0.8987	High Similarity	NPD7075	Discontinued
0.897	High Similarity	NPD4338	Clinical (unspecified phase)
0.8889	High Similarity	NPD6167	Clinical (unspecified phase)
0.8889	High Similarity	NPD6166	Phase 2
0.8889	High Similarity	NPD6168	Clinical (unspecified phase)
0.8854	High Similarity	NPD6801	Discontinued
0.8846	High Similarity	NPD4380	Phase 2
0.8797	High Similarity	NPD7096	Clinical (unspecified phase)
0.878	High Similarity	NPD3818	Discontinued
0.8701	High Similarity	NPD6799	Approved
0.8675	High Similarity	NPD1550	Clinical (unspecified phase)
0.8675	High Similarity	NPD1552	Clinical (unspecified phase)
0.8654	High Similarity	NPD5403	Approved
0.8645	High Similarity	NPD4378	Clinical (unspecified phase)
0.8618	High Similarity	NPD1549	Phase 2
0.8616	High Similarity	NPD1934	Approved
0.8571	High Similarity	NPD6559	Discontinued
0.8562	High Similarity	NPD2393	Clinical (unspecified phase)
0.8526	High Similarity	NPD5401	Approved
0.8509	High Similarity	NPD3817	Phase 2
0.8491	Intermediate Similarity	NPD6599	Discontinued
0.8438	Intermediate Similarity	NPD7411	Suspended
0.8395	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8395	Intermediate Similarity	NPD5402	Approved
0.8344	Intermediate Similarity	NPD3882	Suspended
0.8291	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8247	Intermediate Similarity	NPD2796	Approved
0.8239	Intermediate Similarity	NPD1512	Approved
0.8239	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.8232	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8221	Intermediate Similarity	NPD2801	Approved
0.8187	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8182	Intermediate Similarity	NPD1510	Phase 2
0.8158	Intermediate Similarity	NPD1240	Approved
0.8144	Intermediate Similarity	NPD6959	Discontinued
0.8113	Intermediate Similarity	NPD1511	Approved
0.811	Intermediate Similarity	NPD7819	Suspended
0.8052	Intermediate Similarity	NPD1607	Approved
0.8012	Intermediate Similarity	NPD3751	Discontinued
0.8	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7988	Intermediate Similarity	NPD3787	Discontinued
0.7976	Intermediate Similarity	NPD5494	Approved
0.7943	Intermediate Similarity	NPD8313	Approved
0.7943	Intermediate Similarity	NPD8312	Approved
0.7892	Intermediate Similarity	NPD8455	Phase 2
0.7861	Intermediate Similarity	NPD7584	Approved
0.7857	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7826	Intermediate Similarity	NPD6780	Approved
0.7826	Intermediate Similarity	NPD6779	Approved
0.7826	Intermediate Similarity	NPD6776	Approved
0.7826	Intermediate Similarity	NPD6782	Approved
0.7826	Intermediate Similarity	NPD6781	Approved
0.7826	Intermediate Similarity	NPD6778	Approved
0.7826	Intermediate Similarity	NPD6777	Approved
0.7812	Intermediate Similarity	NPD4628	Phase 3
0.7812	Intermediate Similarity	NPD3750	Approved
0.7812	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7798	Intermediate Similarity	NPD7768	Phase 2
0.7796	Intermediate Similarity	NPD7435	Discontinued
0.7792	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7759	Intermediate Similarity	NPD5844	Phase 1
0.7751	Intermediate Similarity	NPD3749	Approved
0.775	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7733	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7701	Intermediate Similarity	NPD7698	Approved
0.7701	Intermediate Similarity	NPD7696	Phase 3
0.7701	Intermediate Similarity	NPD7697	Approved
0.7679	Intermediate Similarity	NPD1465	Phase 2
0.7677	Intermediate Similarity	NPD6798	Discontinued
0.7674	Intermediate Similarity	NPD6232	Discontinued
0.7673	Intermediate Similarity	NPD1551	Phase 2
0.7644	Intermediate Similarity	NPD7473	Discontinued
0.7636	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7632	Intermediate Similarity	NPD7701	Phase 2
0.7616	Intermediate Similarity	NPD7199	Phase 2
0.76	Intermediate Similarity	NPD7228	Approved
0.7592	Intermediate Similarity	NPD8151	Discontinued
0.759	Intermediate Similarity	NPD1653	Approved
0.7578	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7566	Intermediate Similarity	NPD7871	Phase 2
0.7566	Intermediate Similarity	NPD7870	Phase 2
0.7554	Intermediate Similarity	NPD6535	Approved
0.7554	Intermediate Similarity	NPD6534	Approved
0.7552	Intermediate Similarity	NPD7874	Approved
0.7552	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.755	Intermediate Similarity	NPD1091	Approved
0.7532	Intermediate Similarity	NPD1933	Approved
0.7531	Intermediate Similarity	NPD2800	Approved
0.7527	Intermediate Similarity	NPD7699	Phase 2
0.7527	Intermediate Similarity	NPD7700	Phase 2
0.7516	Intermediate Similarity	NPD6233	Phase 2
0.7513	Intermediate Similarity	NPD7783	Phase 2
0.7513	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD3748	Approved
0.75	Intermediate Similarity	NPD919	Approved
0.75	Intermediate Similarity	NPD7033	Discontinued
0.7486	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD6651	Approved
0.7474	Intermediate Similarity	NPD8319	Approved
0.7474	Intermediate Similarity	NPD8320	Phase 1
0.7472	Intermediate Similarity	NPD5953	Discontinued
0.7468	Intermediate Similarity	NPD1613	Approved
0.7468	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7459	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7458	Intermediate Similarity	NPD7286	Phase 2
0.7453	Intermediate Similarity	NPD2935	Discontinued
0.7448	Intermediate Similarity	NPD7585	Approved
0.744	Intermediate Similarity	NPD7458	Discontinued
0.7436	Intermediate Similarity	NPD6832	Phase 2
0.7436	Intermediate Similarity	NPD4908	Phase 1
0.7434	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.743	Intermediate Similarity	NPD7685	Pre-registration
0.7429	Intermediate Similarity	NPD3926	Phase 2
0.7425	Intermediate Similarity	NPD920	Approved
0.7423	Intermediate Similarity	NPD7801	Approved
0.7421	Intermediate Similarity	NPD6355	Discontinued
0.7414	Intermediate Similarity	NPD1247	Approved
0.7412	Intermediate Similarity	NPD37	Approved
0.741	Intermediate Similarity	NPD2534	Approved
0.741	Intermediate Similarity	NPD2532	Approved
0.741	Intermediate Similarity	NPD2533	Approved
0.7407	Intermediate Similarity	NPD7266	Discontinued
0.7399	Intermediate Similarity	NPD6234	Discontinued
0.7396	Intermediate Similarity	NPD7583	Approved
0.7389	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7384	Intermediate Similarity	NPD4966	Approved
0.7384	Intermediate Similarity	NPD4965	Approved
0.7384	Intermediate Similarity	NPD4967	Phase 2
0.7368	Intermediate Similarity	NPD6823	Phase 2
0.7366	Intermediate Similarity	NPD4360	Phase 2
0.7366	Intermediate Similarity	NPD4363	Phase 3
0.7355	Intermediate Similarity	NPD1203	Approved
0.7349	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7342	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7337	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD6190	Approved
0.7322	Intermediate Similarity	NPD8434	Phase 2
0.7317	Intermediate Similarity	NPD1243	Approved
0.7317	Intermediate Similarity	NPD1652	Phase 2
0.7312	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD5124	Phase 1
0.7308	Intermediate Similarity	NPD2798	Approved
0.7305	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7305	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7301	Intermediate Similarity	NPD2344	Approved
0.7289	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7284	Intermediate Similarity	NPD2799	Discontinued
0.7251	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD943	Approved
0.7239	Intermediate Similarity	NPD6100	Approved
0.7239	Intermediate Similarity	NPD6099	Approved
0.7238	Intermediate Similarity	NPD7240	Approved
0.7235	Intermediate Similarity	NPD3226	Approved
0.7233	Intermediate Similarity	NPD3268	Approved
0.7233	Intermediate Similarity	NPD2313	Discontinued
0.7229	Intermediate Similarity	NPD2354	Approved
0.7229	Intermediate Similarity	NPD3887	Approved
0.7228	Intermediate Similarity	NPD8150	Discontinued
0.7215	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7208	Intermediate Similarity	NPD1610	Phase 2
0.7188	Intermediate Similarity	NPD4062	Phase 3
0.7178	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.7171	Intermediate Similarity	NPD1548	Phase 1
0.717	Intermediate Similarity	NPD3027	Phase 3
0.7161	Intermediate Similarity	NPD9717	Approved
0.7152	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7390	Discontinued
0.7134	Intermediate Similarity	NPD2797	Approved
0.7128	Intermediate Similarity	NPD6212	Phase 3
0.7128	Intermediate Similarity	NPD6213	Phase 3
0.7128	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD2309	Approved
0.7117	Intermediate Similarity	NPD7097	Phase 1
0.7101	Intermediate Similarity	NPD4662	Approved
0.7101	Intermediate Similarity	NPD4661	Approved
0.7099	Intermediate Similarity	NPD230	Phase 1
0.7097	Intermediate Similarity	NPD422	Phase 1
0.7095	Intermediate Similarity	NPD2403	Approved
0.7091	Intermediate Similarity	NPD2346	Discontinued
0.707	Intermediate Similarity	NPD3225	Approved
0.7066	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD5049	Phase 3
0.7048	Intermediate Similarity	NPD2424	Discontinued
0.7037	Intermediate Similarity	NPD4060	Phase 1
0.7035	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7011	Intermediate Similarity	NPD6844	Discontinued
0.7006	Intermediate Similarity	NPD2654	Approved
0.6995	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD447	Suspended
0.6994	Remote Similarity	NPD4340	Discontinued
0.699	Remote Similarity	NPD7211	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