NPASS Compound

Structure

CID223747 OpenBabel06191716022D 33 36 0 0 1 0 0 0 0 0999 V2000 1.7321 -0.0000 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 -3.4641 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 -4.3301 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 4.0000 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 0.8660 -0.5000 0.0000 C 0 0 1 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 -0.8660 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -2.0000 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 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 1 0 0 0 0 0 0 0 0 0 -0.8660 5.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 2.5000 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 1.0000 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 -6.0622 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 -2.5981 2.5000 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 2 30 1 0 0 0 0 3 4 2 0 0 0 0 3 9 1 0 0 0 0 4 11 1 0 0 0 0 5 9 2 0 0 0 0 5 13 1 0 0 0 0 6 10 2 0 0 0 0 6 12 1 0 0 0 0 7 10 1 0 0 0 0 7 14 2 0 0 0 0 8 1 1 1 0 0 0 8 16 1 0 0 0 0 8 31 1 0 0 0 0 9 20 1 0 0 0 0 10 23 1 0 0 0 0 11 13 2 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 30 1 0 0 0 0 14 15 1 0 0 0 0 14 32 1 0 0 0 0 15 17 1 0 0 0 0 16 18 1 0 0 0 0 16 26 1 6 0 0 0 17 21 1 0 0 0 0 17 27 2 0 0 0 0 18 19 1 0 0 0 0 18 28 1 1 0 0 0 19 22 1 0 0 0 0 19 29 1 1 0 0 0 20 21 2 0 0 0 0 20 32 1 0 0 0 0 21 33 1 0 0 0 0 22 31 1 0 0 0 0 22 33 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	386.14
Volume:	386.543
LogP:	4.097
LogD:	2.883
LogS:	-3.522
# Rotatable Bonds:	4
TPSA:	116.45
# H-Bond Aceptor:	7
# H-Bond Donor:	4
# Rings:	3
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.592
Synthetic Accessibility Score:	3.407
Fsp3:	0.286
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.027
MDCK Permeability:	9.184905138681643e-06
Pgp-inhibitor:	0.373
Pgp-substrate:	0.684
Human Intestinal Absorption (HIA):	0.042
20% Bioavailability (F20%):	0.298
30% Bioavailability (F30%):	0.985

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.004
Plasma Protein Binding (PPB):	92.72254943847656%
Volume Distribution (VD):	0.68
Pgp-substrate:	8.641613006591797%

ADMET: Metabolism

CYP1A2-inhibitor:	0.451
CYP1A2-substrate:	0.902
CYP2C19-inhibitor:	0.719
CYP2C19-substrate:	0.065
CYP2C9-inhibitor:	0.824
CYP2C9-substrate:	0.889
CYP2D6-inhibitor:	0.728
CYP2D6-substrate:	0.361
CYP3A4-inhibitor:	0.363
CYP3A4-substrate:	0.17

ADMET: Excretion

Clearance (CL):	16.732
Half-life (T1/2):	0.647

ADMET: Toxicity

hERG Blockers:	0.03
Human Hepatotoxicity (H-HT):	0.657
Drug-inuced Liver Injury (DILI):	0.934
AMES Toxicity:	0.053
Rat Oral Acute Toxicity:	0.811
Maximum Recommended Daily Dose:	0.781
Skin Sensitization:	0.94
Carcinogencity:	0.212
Eye Corrosion:	0.003
Eye Irritation:	0.892
Respiratory Toxicity:	0.905

Download Data

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

Natural Product: NPC223747

Natural Product ID:	NPC223747
*Common Name:**	Isorhamnetin 3-O-Rhamnoside
IUPAC Name:	5,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxychromen-4-one
Synonyms:	Isorhamnetin 3-O-Rhamnoside
Standard InCHIKey:	UXXAEVMOIUAYQT-UFGFRKJLSA-N
Standard InCHI:	InChI=1S/C22H22O11/c1-8-16(26)18(28)19(29)22(31-8)33-21-17(27)15-12(25)6-10(23)7-14(15)32-20(21)9-3-4-11(24)13(5-9)30-2/h3-8,16,18-19,22-26,28-29H,1-2H3/t8-,16-,18+,19+,22-/m0/s1
SMILES:	C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)Oc1c(=O)c2c(cc(cc2oc1c1ccc(c(c1)OC)O)O)O)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL485261
PubChem CID:	23634491
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
NPO28679	Prunus mume	Species	Rosaceae	Eukaryota	flowers	n.a.	n.a.	PMID[12193020]
NPO28679	Prunus mume	Species	Rosaceae	Eukaryota	fruits	n.a.	n.a.	PMID[24485782]
NPO28679	Prunus mume	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28679	Prunus mume	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28679	Prunus mume	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO28679	Prunus mume	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO28679	Prunus mume	Species	Rosaceae	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
NPT68	Individual Protein	Aldose reductase	Rattus norvegicus	IC50	=	19000.0	nM	PMID[498586]

☑ 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 NPC223747 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	440
0.1-0.2	1822
0.2-0.3	4199
0.3-0.4	9805
0.4-0.5	8237
0.5-0.6	4214
0.6-0.7	5210
0.7-0.8	5295
0.8-0.85	1669
0.85-0.9	1102
0.9-0.95	496
0.95-1	208

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC120099
1.0	High Similarity	NPC203050
1.0	High Similarity	NPC219904
1.0	High Similarity	NPC225434
0.9937	High Similarity	NPC52550
0.9937	High Similarity	NPC265530
0.9937	High Similarity	NPC325555
0.9937	High Similarity	NPC226304
0.9937	High Similarity	NPC223424
0.9937	High Similarity	NPC127546
0.9937	High Similarity	NPC84362
0.9937	High Similarity	NPC173637
0.9937	High Similarity	NPC317489
0.9937	High Similarity	NPC206123
0.9875	High Similarity	NPC153755
0.9873	High Similarity	NPC328940
0.9873	High Similarity	NPC145038
0.9873	High Similarity	NPC73855
0.9873	High Similarity	NPC118284
0.9873	High Similarity	NPC88789
0.9873	High Similarity	NPC56077
0.9873	High Similarity	NPC253662
0.9873	High Similarity	NPC21100
0.9873	High Similarity	NPC276222
0.9873	High Similarity	NPC308404
0.9873	High Similarity	NPC179950
0.9873	High Similarity	NPC274618
0.9873	High Similarity	NPC135599
0.9873	High Similarity	NPC113968
0.9873	High Similarity	NPC281131
0.9873	High Similarity	NPC277174
0.9873	High Similarity	NPC197285
0.9814	High Similarity	NPC24043
0.9814	High Similarity	NPC169977
0.9814	High Similarity	NPC42773
0.9814	High Similarity	NPC4390
0.9814	High Similarity	NPC45522
0.9814	High Similarity	NPC21666
0.9814	High Similarity	NPC101026
0.9812	High Similarity	NPC95866
0.9812	High Similarity	NPC244776
0.9812	High Similarity	NPC116864
0.981	High Similarity	NPC22832
0.981	High Similarity	NPC311830
0.981	High Similarity	NPC19388
0.981	High Similarity	NPC240431
0.981	High Similarity	NPC55786
0.981	High Similarity	NPC277205
0.9753	High Similarity	NPC16194
0.9753	High Similarity	NPC220173
0.9753	High Similarity	NPC19108
0.9753	High Similarity	NPC476472
0.9753	High Similarity	NPC294815
0.9753	High Similarity	NPC473327
0.9752	High Similarity	NPC134532
0.9752	High Similarity	NPC203259
0.9752	High Similarity	NPC471748
0.9752	High Similarity	NPC476405
0.9752	High Similarity	NPC117260
0.9752	High Similarity	NPC175107
0.9752	High Similarity	NPC26230
0.9752	High Similarity	NPC245452
0.9752	High Similarity	NPC190003
0.9752	High Similarity	NPC176740
0.9752	High Similarity	NPC471725
0.9752	High Similarity	NPC155877
0.9752	High Similarity	NPC60735
0.9752	High Similarity	NPC33054
0.975	High Similarity	NPC270578
0.975	High Similarity	NPC52382
0.9747	High Similarity	NPC222936
0.9747	High Similarity	NPC309025
0.9747	High Similarity	NPC243930
0.9747	High Similarity	NPC270335
0.9747	High Similarity	NPC19709
0.9747	High Similarity	NPC284960
0.9747	High Similarity	NPC88023
0.9747	High Similarity	NPC191306
0.9693	High Similarity	NPC472385
0.9693	High Similarity	NPC198324
0.9689	High Similarity	NPC67105
0.9689	High Similarity	NPC245014
0.9689	High Similarity	NPC84265
0.9689	High Similarity	NPC259896
0.9689	High Similarity	NPC235260
0.9689	High Similarity	NPC156869
0.9689	High Similarity	NPC155763
0.9689	High Similarity	NPC20505
0.9689	High Similarity	NPC255157
0.9689	High Similarity	NPC254855
0.9689	High Similarity	NPC285197
0.9689	High Similarity	NPC136042
0.9689	High Similarity	NPC29958
0.9689	High Similarity	NPC282987
0.9689	High Similarity	NPC67326
0.9688	High Similarity	NPC229729
0.9688	High Similarity	NPC160156
0.9688	High Similarity	NPC92565
0.9684	High Similarity	NPC473043
0.9684	High Similarity	NPC189142
0.9684	High Similarity	NPC77660
0.9634	High Similarity	NPC89052
0.9634	High Similarity	NPC217520
0.9634	High Similarity	NPC168584
0.9634	High Similarity	NPC173837
0.9634	High Similarity	NPC139571
0.9634	High Similarity	NPC251417
0.9632	High Similarity	NPC210094
0.9632	High Similarity	NPC264735
0.9632	High Similarity	NPC477848
0.9632	High Similarity	NPC135277
0.9632	High Similarity	NPC43211
0.9632	High Similarity	NPC115760
0.9632	High Similarity	NPC294629
0.9632	High Similarity	NPC49344
0.9632	High Similarity	NPC237435
0.9632	High Similarity	NPC101191
0.9627	High Similarity	NPC195257
0.9627	High Similarity	NPC226294
0.9627	High Similarity	NPC227508
0.9627	High Similarity	NPC45638
0.9627	High Similarity	NPC58053
0.9627	High Similarity	NPC209296
0.9627	High Similarity	NPC138927
0.9627	High Similarity	NPC475942
0.9627	High Similarity	NPC186807
0.9627	High Similarity	NPC93337
0.9627	High Similarity	NPC469931
0.9627	High Similarity	NPC201292
0.9627	High Similarity	NPC105025
0.9625	High Similarity	NPC210073
0.9625	High Similarity	NPC236934
0.9625	High Similarity	NPC5778
0.9625	High Similarity	NPC115674
0.9625	High Similarity	NPC255615
0.9625	High Similarity	NPC254306
0.9625	High Similarity	NPC67037
0.9623	High Similarity	NPC168822
0.962	High Similarity	NPC182045
0.9576	High Similarity	NPC126784
0.9576	High Similarity	NPC241423
0.9576	High Similarity	NPC473571
0.9576	High Similarity	NPC470443
0.9576	High Similarity	NPC110941
0.9576	High Similarity	NPC192539
0.9576	High Similarity	NPC470444
0.9576	High Similarity	NPC473682
0.9573	High Similarity	NPC169733
0.9573	High Similarity	NPC470949
0.9573	High Similarity	NPC202908
0.9573	High Similarity	NPC122467
0.9573	High Similarity	NPC89127
0.9573	High Similarity	NPC65563
0.9573	High Similarity	NPC233994
0.9573	High Similarity	NPC48984
0.9573	High Similarity	NPC211532
0.9573	High Similarity	NPC8573
0.9573	High Similarity	NPC219043
0.9573	High Similarity	NPC471669
0.9573	High Similarity	NPC292019
0.9573	High Similarity	NPC14187
0.9568	High Similarity	NPC231194
0.9568	High Similarity	NPC51326
0.9568	High Similarity	NPC72249
0.9565	High Similarity	NPC149244
0.9565	High Similarity	NPC58716
0.9565	High Similarity	NPC48640
0.9565	High Similarity	NPC275454
0.9565	High Similarity	NPC146792
0.9565	High Similarity	NPC45618
0.9563	High Similarity	NPC34531
0.956	High Similarity	NPC300537
0.956	High Similarity	NPC127782
0.9557	High Similarity	NPC110349
0.9518	High Similarity	NPC473073
0.9518	High Similarity	NPC473071
0.9515	High Similarity	NPC35167
0.9515	High Similarity	NPC477895
0.9512	High Similarity	NPC253685
0.9512	High Similarity	NPC223426
0.9512	High Similarity	NPC81042
0.9512	High Similarity	NPC34267
0.9512	High Similarity	NPC214621
0.9509	High Similarity	NPC307518
0.9509	High Similarity	NPC256760
0.9509	High Similarity	NPC254540
0.9509	High Similarity	NPC211594
0.9509	High Similarity	NPC172807
0.9509	High Similarity	NPC235575
0.9509	High Similarity	NPC205076
0.9509	High Similarity	NPC48773
0.9506	High Similarity	NPC86008
0.9506	High Similarity	NPC476771
0.9506	High Similarity	NPC229687
0.9503	High Similarity	NPC8856
0.95	High Similarity	NPC29830
0.95	High Similarity	NPC88043
0.9494	High Similarity	NPC320283
0.9494	High Similarity	NPC472459
0.9494	High Similarity	NPC111929

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 NPC223747 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	404
0.1-0.2	944
0.2-0.3	1949
0.3-0.4	2684
0.4-0.5	1792
0.5-0.6	910
0.6-0.7	296
0.7-0.8	129
0.8-0.85	13
0.85-0.9	16
0.9-0.95	11
0.95-1	2

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9752	High Similarity	NPD6797	Phase 2
0.9691	High Similarity	NPD7251	Discontinued
0.9632	High Similarity	NPD4338	Clinical (unspecified phase)
0.9632	High Similarity	NPD7808	Phase 3
0.9627	High Similarity	NPD7054	Approved
0.9568	High Similarity	NPD7472	Approved
0.9448	High Similarity	NPD7074	Phase 3
0.9325	High Similarity	NPD3818	Discontinued
0.9202	High Similarity	NPD6166	Phase 2
0.9202	High Similarity	NPD6167	Clinical (unspecified phase)
0.9202	High Similarity	NPD6168	Clinical (unspecified phase)
0.9187	High Similarity	NPD4381	Clinical (unspecified phase)
0.9152	High Similarity	NPD7804	Clinical (unspecified phase)
0.9062	High Similarity	NPD3817	Phase 2
0.9057	High Similarity	NPD1934	Approved
0.8889	High Similarity	NPD3882	Suspended
0.8882	High Similarity	NPD2393	Clinical (unspecified phase)
0.8882	High Similarity	NPD2801	Approved
0.8797	High Similarity	NPD1512	Approved
0.8671	High Similarity	NPD1511	Approved
0.8606	High Similarity	NPD7075	Discontinued
0.858	High Similarity	NPD4380	Phase 2
0.8545	High Similarity	NPD4868	Clinical (unspecified phase)
0.8485	Intermediate Similarity	NPD5402	Approved
0.8476	Intermediate Similarity	NPD6801	Discontinued
0.8439	Intermediate Similarity	NPD6559	Discontinued
0.8424	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8395	Intermediate Similarity	NPD5403	Approved
0.8385	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8382	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8323	Intermediate Similarity	NPD6799	Approved
0.8272	Intermediate Similarity	NPD5401	Approved
0.8232	Intermediate Similarity	NPD1653	Approved
0.8176	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8176	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8176	Intermediate Similarity	NPD5494	Approved
0.8125	Intermediate Similarity	NPD1549	Phase 2
0.8122	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.8103	Intermediate Similarity	NPD3751	Discontinued
0.8081	Intermediate Similarity	NPD3787	Discontinued
0.8057	Intermediate Similarity	NPD5844	Phase 1
0.8047	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8035	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.8024	Intermediate Similarity	NPD6599	Discontinued
0.8023	Intermediate Similarity	NPD7685	Pre-registration
0.8	Intermediate Similarity	NPD2796	Approved
0.7988	Intermediate Similarity	NPD1465	Phase 2
0.7988	Intermediate Similarity	NPD7819	Suspended
0.7977	Intermediate Similarity	NPD6232	Discontinued
0.7976	Intermediate Similarity	NPD7411	Suspended
0.7952	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7943	Intermediate Similarity	NPD7473	Discontinued
0.7939	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7937	Intermediate Similarity	NPD1510	Phase 2
0.7919	Intermediate Similarity	NPD7199	Phase 2
0.7919	Intermediate Similarity	NPD6959	Discontinued
0.7907	Intermediate Similarity	NPD919	Approved
0.7898	Intermediate Similarity	NPD7228	Approved
0.7845	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7816	Intermediate Similarity	NPD1247	Approved
0.7803	Intermediate Similarity	NPD6234	Discontinued
0.7799	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7799	Intermediate Similarity	NPD1613	Approved
0.7758	Intermediate Similarity	NPD6190	Approved
0.7735	Intermediate Similarity	NPD8312	Approved
0.7735	Intermediate Similarity	NPD8313	Approved
0.773	Intermediate Similarity	NPD7266	Discontinued
0.7727	Intermediate Similarity	NPD3926	Phase 2
0.7725	Intermediate Similarity	NPD6776	Approved
0.7725	Intermediate Similarity	NPD6781	Approved
0.7725	Intermediate Similarity	NPD6779	Approved
0.7725	Intermediate Similarity	NPD6780	Approved
0.7725	Intermediate Similarity	NPD6782	Approved
0.7725	Intermediate Similarity	NPD6778	Approved
0.7725	Intermediate Similarity	NPD6777	Approved
0.7719	Intermediate Similarity	NPD37	Approved
0.7717	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7697	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7696	Intermediate Similarity	NPD7435	Discontinued
0.7688	Intermediate Similarity	NPD4967	Phase 2
0.7688	Intermediate Similarity	NPD1240	Approved
0.7688	Intermediate Similarity	NPD4965	Approved
0.7688	Intermediate Similarity	NPD4966	Approved
0.7684	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7683	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7668	Intermediate Similarity	NPD7584	Approved
0.7665	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.764	Intermediate Similarity	NPD1933	Approved
0.761	Intermediate Similarity	NPD3027	Phase 3
0.7593	Intermediate Similarity	NPD1607	Approved
0.759	Intermediate Similarity	NPD3750	Approved
0.7578	Intermediate Similarity	NPD943	Approved
0.7566	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7547	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7531	Intermediate Similarity	NPD230	Phase 1
0.7513	Intermediate Similarity	NPD7697	Approved
0.7513	Intermediate Similarity	NPD7698	Approved
0.7513	Intermediate Similarity	NPD7696	Phase 3
0.75	Intermediate Similarity	NPD8151	Discontinued
0.7486	Intermediate Similarity	NPD7768	Phase 2
0.7485	Intermediate Similarity	NPD4628	Phase 3
0.7484	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7474	Intermediate Similarity	NPD7871	Phase 2
0.7474	Intermediate Similarity	NPD7870	Phase 2
0.7471	Intermediate Similarity	NPD8455	Phase 2
0.7462	Intermediate Similarity	NPD7874	Approved
0.7462	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.746	Intermediate Similarity	NPD6534	Approved
0.746	Intermediate Similarity	NPD6535	Approved
0.7455	Intermediate Similarity	NPD1551	Phase 2
0.7453	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7449	Intermediate Similarity	NPD7701	Phase 2
0.7443	Intermediate Similarity	NPD3749	Approved
0.7432	Intermediate Similarity	NPD7240	Approved
0.7423	Intermediate Similarity	NPD447	Suspended
0.7394	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7349	Intermediate Similarity	NPD2935	Discontinued
0.7344	Intermediate Similarity	NPD7700	Phase 2
0.7344	Intermediate Similarity	NPD7699	Phase 2
0.7337	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7337	Intermediate Similarity	NPD7801	Approved
0.7337	Intermediate Similarity	NPD7783	Phase 2
0.7321	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD2533	Approved
0.731	Intermediate Similarity	NPD2534	Approved
0.731	Intermediate Similarity	NPD2532	Approved
0.7296	Intermediate Similarity	NPD8319	Approved
0.7296	Intermediate Similarity	NPD8320	Phase 1
0.7293	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7289	Intermediate Similarity	NPD3748	Approved
0.7282	Intermediate Similarity	NPD6823	Phase 2
0.7273	Intermediate Similarity	NPD7585	Approved
0.7268	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7239	Intermediate Similarity	NPD6798	Discontinued
0.7234	Intermediate Similarity	NPD8434	Phase 2
0.7234	Intermediate Similarity	NPD8150	Discontinued
0.7225	Intermediate Similarity	NPD920	Approved
0.7222	Intermediate Similarity	NPD7583	Approved
0.7219	Intermediate Similarity	NPD6674	Discontinued
0.7219	Intermediate Similarity	NPD2800	Approved
0.7215	Intermediate Similarity	NPD1091	Approved
0.7209	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7204	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7195	Intermediate Similarity	NPD6233	Phase 2
0.7189	Intermediate Similarity	NPD5953	Discontinued
0.7188	Intermediate Similarity	NPD4360	Phase 2
0.7188	Intermediate Similarity	NPD4363	Phase 3
0.7186	Intermediate Similarity	NPD7033	Discontinued
0.716	Intermediate Similarity	NPD9494	Approved
0.7143	Intermediate Similarity	NPD6099	Approved
0.7143	Intermediate Similarity	NPD7458	Discontinued
0.7143	Intermediate Similarity	NPD3226	Approved
0.7143	Intermediate Similarity	NPD6100	Approved
0.7128	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7125	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7119	Intermediate Similarity	NPD6844	Discontinued
0.7118	Intermediate Similarity	NPD1652	Phase 2
0.7118	Intermediate Similarity	NPD1243	Approved
0.7117	Intermediate Similarity	NPD6832	Phase 2
0.7117	Intermediate Similarity	NPD4908	Phase 1
0.7115	Intermediate Similarity	NPD5619	Clinical (unspecified phase)
0.711	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7108	Intermediate Similarity	NPD6355	Discontinued
0.7101	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD2798	Approved
0.7093	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD7286	Phase 2
0.7071	Intermediate Similarity	NPD7680	Approved
0.7066	Intermediate Similarity	NPD6651	Approved
0.7052	Intermediate Similarity	NPD7390	Discontinued
0.7047	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.7047	Intermediate Similarity	NPD6213	Phase 3
0.7047	Intermediate Similarity	NPD6212	Phase 3
0.7039	Intermediate Similarity	NPD5353	Approved
0.7037	Intermediate Similarity	NPD1203	Approved
0.703	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD2313	Discontinued
0.7027	Intermediate Similarity	NPD2163	Approved
0.7006	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD5124	Phase 1
0.7006	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD2346	Discontinued
0.7	Intermediate Similarity	NPD2344	Approved
0.6982	Remote Similarity	NPD2799	Discontinued
0.6977	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6962	Remote Similarity	NPD1548	Phase 1
0.6957	Remote Similarity	NPD5242	Approved
0.6949	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6946	Remote Similarity	NPD4060	Phase 1
0.694	Remote Similarity	NPD8127	Discontinued
0.6935	Remote Similarity	NPD5005	Approved
0.6935	Remote Similarity	NPD5006	Approved
0.6928	Remote Similarity	NPD3268	Approved
0.6927	Remote Similarity	NPD6841	Approved
0.6927	Remote Similarity	NPD6843	Phase 3
0.6927	Remote Similarity	NPD6842	Approved
0.6919	Remote Similarity	NPD2403	Approved
0.6915	Remote Similarity	NPD7211	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD7422	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