NPASS Compound

Structure

NPC475942 OpenBabel07101718232D 32 35 0 0 1 0 0 0 0 0999 V2000 -2.5981 2.5000 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 3.4641 4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 2.5000 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 1.7321 -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 -2.5981 1.5000 0.0000 C 0 0 1 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 5.1962 4.0000 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 -3.4641 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 0 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 5.1962 3.0000 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 -1.7321 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 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 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 4.5000 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 -4.3301 -0.5000 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 -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 6.0622 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 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 -0.8660 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 29 1 0 0 0 0 3 4 2 0 0 0 0 3 10 1 0 0 0 0 4 11 1 0 0 0 0 5 10 2 0 0 0 0 5 16 1 0 0 0 0 6 12 1 0 0 0 0 6 15 2 0 0 0 0 7 14 2 0 0 0 0 7 17 1 0 0 0 0 8 13 1 0 0 0 0 8 18 1 0 0 0 0 9 1 1 6 0 0 0 9 20 1 0 0 0 0 9 30 1 0 0 0 0 10 15 1 0 0 0 0 11 16 2 0 0 0 0 11 23 1 0 0 0 0 12 19 1 0 0 0 0 12 24 2 0 0 0 0 13 20 1 0 0 0 0 13 25 1 1 0 0 0 14 22 1 0 0 0 0 14 26 1 0 0 0 0 15 31 1 0 0 0 0 16 29 1 0 0 0 0 17 19 2 0 0 0 0 17 31 1 0 0 0 0 18 30 1 0 0 0 0 18 32 1 1 0 0 0 19 21 1 0 0 0 0 20 27 1 6 0 0 0 21 22 2 0 0 0 0 21 28 1 0 0 0 0 22 32 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	446.12
Volume:	421.653
LogP:	2.519
LogD:	1.549
LogS:	-3.981
# Rotatable Bonds:	4
TPSA:	159.05
# H-Bond Aceptor:	10
# H-Bond Donor:	5
# Rings:	4
# Heavy Atoms:	10

MedChem Properties

QED Drug-Likeness Score:	0.4
Synthetic Accessibility Score:	4.004
Fsp3:	0.318
Lipinski Rule-of-5:	Accepted
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:	-5.009
MDCK Permeability:	2.2741927750757895e-05
Pgp-inhibitor:	0.187
Pgp-substrate:	0.959
Human Intestinal Absorption (HIA):	0.034
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.916

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.011
Plasma Protein Binding (PPB):	91.21080017089844%
Volume Distribution (VD):	0.719
Pgp-substrate:	13.195069313049316%

ADMET: Metabolism

CYP1A2-inhibitor:	0.428
CYP1A2-substrate:	0.894
CYP2C19-inhibitor:	0.044
CYP2C19-substrate:	0.067
CYP2C9-inhibitor:	0.48
CYP2C9-substrate:	0.82
CYP2D6-inhibitor:	0.226
CYP2D6-substrate:	0.289
CYP3A4-inhibitor:	0.247
CYP3A4-substrate:	0.101

ADMET: Excretion

Clearance (CL):	7.506
Half-life (T1/2):	0.806

ADMET: Toxicity

hERG Blockers:	0.108
Human Hepatotoxicity (H-HT):	0.272
Drug-inuced Liver Injury (DILI):	0.954
AMES Toxicity:	0.578
Rat Oral Acute Toxicity:	0.035
Maximum Recommended Daily Dose:	0.831
Skin Sensitization:	0.9
Carcinogencity:	0.626
Eye Corrosion:	0.003
Eye Irritation:	0.327
Respiratory Toxicity:	0.506

Download Data

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

Natural Product: NPC475942

Natural Product ID:	NPC475942
*Common Name:**	Alternanthin
IUPAC Name:	6-[(2S,4R,5S,6S)-4,5-dihydroxy-6-methyloxan-2-yl]oxy-5,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)chromen-4-one
Synonyms:	Alternanthin
Standard InCHIKey:	LORQHSFIQJBWBT-DKVFDIBASA-N
Standard InCHI:	InChI=1S/C22H22O10/c1-9-20(27)13(25)8-18(30-9)32-22-14(26)7-17-19(21(22)28)12(24)6-15(31-17)10-3-4-11(23)16(5-10)29-2/h3-7,9,13,18,20,23,25-28H,8H2,1-2H3/t9-,13+,18-,20+/m0/s1
SMILES:	COc1cc(ccc1O)c1cc(=O)c2c(o1)cc(c(c2O)O[C@H]1C[C@@H](O)[C@@H]([C@@H](O1)C)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL519071
PubChem CID:	44559262
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001111] Flavonoid glycosides [CHEMONTID:0001583] Flavonoid 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
NPO7863	Dioscorea opposita	Species	Dioscoreaceae	Eukaryota	aerial parts	n.a.	n.a.	PMID[16124773]
NPO7863	Dioscorea opposita	Species	Dioscoreaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO7863	Dioscorea opposita	Species	Dioscoreaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO7863	Dioscorea opposita	Species	Dioscoreaceae	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
Others	9

Activity Type	# Activity
Others	3
Tissue	6

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified		Activity	=	25.08	%	PMID[480936]
NPT2	Others	Unspecified		Activity	=	28.29	%	PMID[480936]
NPT2	Others	Unspecified		Activity	=	38.12	%	PMID[480936]
NPT2535	Tissue	Plasma	Oryctolagus cuniculus	Activity	=	70.27	%	PMID[480936]
NPT2535	Tissue	Plasma	Oryctolagus cuniculus	Activity	=	96.06	%	PMID[480936]
NPT2535	Tissue	Plasma	Oryctolagus cuniculus	Activity	=	129.42	%	PMID[480936]
NPT632	Tissue	Brain	Rattus norvegicus	Activity	=	1.4	mmol	PMID[480936]
NPT632	Tissue	Brain	Rattus norvegicus	Activity	=	1.34	mmol	PMID[480936]
NPT632	Tissue	Brain	Rattus norvegicus	Activity	=	1.57	mmol	PMID[480936]

☑ 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 NPC475942 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	434
0.1-0.2	1831
0.2-0.3	4170
0.3-0.4	9832
0.4-0.5	8312
0.5-0.6	4081
0.6-0.7	5099
0.7-0.8	5351
0.8-0.85	1641
0.85-0.9	1345
0.9-0.95	441
0.95-1	160

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC201292
1.0	High Similarity	NPC45638
1.0	High Similarity	NPC58053
1.0	High Similarity	NPC469931
1.0	High Similarity	NPC186807
1.0	High Similarity	NPC105025
1.0	High Similarity	NPC93337
1.0	High Similarity	NPC226294
0.9937	High Similarity	NPC146792
0.9937	High Similarity	NPC58716
0.9937	High Similarity	NPC45618
0.9875	High Similarity	NPC307518
0.9875	High Similarity	NPC48773
0.9875	High Similarity	NPC211594
0.9875	High Similarity	NPC476405
0.9875	High Similarity	NPC172807
0.9875	High Similarity	NPC205076
0.9875	High Similarity	NPC117260
0.9875	High Similarity	NPC254540
0.9814	High Similarity	NPC204693
0.9814	High Similarity	NPC101026
0.9814	High Similarity	NPC24043
0.9814	High Similarity	NPC169977
0.9814	High Similarity	NPC42773
0.9814	High Similarity	NPC45522
0.9814	High Similarity	NPC21666
0.9812	High Similarity	NPC21190
0.9812	High Similarity	NPC22195
0.9812	High Similarity	NPC282987
0.9812	High Similarity	NPC105511
0.9812	High Similarity	NPC245014
0.9812	High Similarity	NPC183357
0.9812	High Similarity	NPC224462
0.9812	High Similarity	NPC84265
0.981	High Similarity	NPC22832
0.981	High Similarity	NPC311830
0.9753	High Similarity	NPC477848
0.9752	High Similarity	NPC3583
0.9752	High Similarity	NPC259152
0.975	High Similarity	NPC170675
0.975	High Similarity	NPC472381
0.975	High Similarity	NPC210042
0.975	High Similarity	NPC471457
0.975	High Similarity	NPC95855
0.975	High Similarity	NPC472383
0.975	High Similarity	NPC112755
0.9748	High Similarity	NPC99957
0.9748	High Similarity	NPC181616
0.9747	High Similarity	NPC222936
0.9747	High Similarity	NPC309025
0.9747	High Similarity	NPC270335
0.9747	High Similarity	NPC243930
0.9747	High Similarity	NPC88023
0.9747	High Similarity	NPC19709
0.9747	High Similarity	NPC94777
0.9747	High Similarity	NPC284960
0.9747	High Similarity	NPC191306
0.9693	High Similarity	NPC169733
0.9693	High Similarity	NPC233994
0.9693	High Similarity	NPC472385
0.9693	High Similarity	NPC198324
0.9693	High Similarity	NPC211532
0.9691	High Similarity	NPC239549
0.9691	High Similarity	NPC236191
0.9691	High Similarity	NPC51774
0.9689	High Similarity	NPC34287
0.9689	High Similarity	NPC474434
0.9689	High Similarity	NPC471416
0.9689	High Similarity	NPC44558
0.9688	High Similarity	NPC93099
0.9688	High Similarity	NPC229729
0.9688	High Similarity	NPC135345
0.9684	High Similarity	NPC189142
0.9684	High Similarity	NPC473043
0.9684	High Similarity	NPC77660
0.9634	High Similarity	NPC168584
0.9632	High Similarity	NPC115760
0.9632	High Similarity	NPC210094
0.9632	High Similarity	NPC264735
0.9632	High Similarity	NPC135277
0.9632	High Similarity	NPC49344
0.9632	High Similarity	NPC472607
0.9632	High Similarity	NPC101191
0.9632	High Similarity	NPC237435
0.9632	High Similarity	NPC43211
0.963	High Similarity	NPC301683
0.963	High Similarity	NPC472386
0.963	High Similarity	NPC267254
0.9627	High Similarity	NPC195257
0.9627	High Similarity	NPC229687
0.9627	High Similarity	NPC223747
0.9627	High Similarity	NPC120099
0.9627	High Similarity	NPC219904
0.9627	High Similarity	NPC183036
0.9627	High Similarity	NPC209296
0.9627	High Similarity	NPC225434
0.9627	High Similarity	NPC203050
0.9625	High Similarity	NPC210073
0.9625	High Similarity	NPC236934
0.9625	High Similarity	NPC5778
0.9625	High Similarity	NPC21100
0.9625	High Similarity	NPC115674
0.9625	High Similarity	NPC197285
0.9623	High Similarity	NPC168822
0.9623	High Similarity	NPC88043
0.962	High Similarity	NPC182045
0.9576	High Similarity	NPC126784
0.9576	High Similarity	NPC241423
0.9576	High Similarity	NPC470444
0.9576	High Similarity	NPC473571
0.9576	High Similarity	NPC470443
0.9576	High Similarity	NPC110941
0.9576	High Similarity	NPC473682
0.9573	High Similarity	NPC472992
0.9573	High Similarity	NPC65563
0.9573	High Similarity	NPC472991
0.9573	High Similarity	NPC8573
0.9573	High Similarity	NPC470949
0.9571	High Similarity	NPC4390
0.9568	High Similarity	NPC206123
0.9568	High Similarity	NPC231194
0.9568	High Similarity	NPC51326
0.9565	High Similarity	NPC84362
0.9565	High Similarity	NPC52550
0.9565	High Similarity	NPC226304
0.9565	High Similarity	NPC317489
0.9565	High Similarity	NPC116745
0.9565	High Similarity	NPC127546
0.9565	High Similarity	NPC265530
0.9565	High Similarity	NPC173637
0.9565	High Similarity	NPC45400
0.9565	High Similarity	NPC325555
0.9565	High Similarity	NPC223424
0.9563	High Similarity	NPC277205
0.9563	High Similarity	NPC165720
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
0.9512	High Similarity	NPC102028
0.9512	High Similarity	NPC142996
0.9509	High Similarity	NPC475155
0.9509	High Similarity	NPC256760
0.9509	High Similarity	NPC153755
0.9509	High Similarity	NPC235575
0.9509	High Similarity	NPC190003
0.9509	High Similarity	NPC156977
0.9509	High Similarity	NPC175107
0.9506	High Similarity	NPC86008
0.9506	High Similarity	NPC471287
0.9503	High Similarity	NPC179950
0.9503	High Similarity	NPC135599
0.9503	High Similarity	NPC88789
0.9503	High Similarity	NPC56077
0.9503	High Similarity	NPC276222
0.9503	High Similarity	NPC253662
0.9503	High Similarity	NPC308404
0.9503	High Similarity	NPC8856
0.9503	High Similarity	NPC118284
0.9503	High Similarity	NPC328940
0.9503	High Similarity	NPC281131
0.9503	High Similarity	NPC113968
0.9503	High Similarity	NPC274618
0.9503	High Similarity	NPC277174
0.9503	High Similarity	NPC145038
0.9503	High Similarity	NPC73855
0.95	High Similarity	NPC29830
0.9461	High Similarity	NPC36138
0.9461	High Similarity	NPC470449
0.9461	High Similarity	NPC470447
0.9461	High Similarity	NPC470445
0.9461	High Similarity	NPC470446
0.9461	High Similarity	NPC473072
0.9455	High Similarity	NPC257714
0.9455	High Similarity	NPC472380
0.9455	High Similarity	NPC472384
0.9455	High Similarity	NPC268533
0.9455	High Similarity	NPC472382
0.9451	High Similarity	NPC172033
0.9451	High Similarity	NPC472993
0.9451	High Similarity	NPC175230
0.9451	High Similarity	NPC88560
0.9451	High Similarity	NPC208668
0.9448	High Similarity	NPC150767
0.9448	High Similarity	NPC20505
0.9448	High Similarity	NPC44328
0.9448	High Similarity	NPC177731
0.9448	High Similarity	NPC293004
0.9448	High Similarity	NPC67105
0.9448	High Similarity	NPC155763
0.9448	High Similarity	NPC212748
0.9448	High Similarity	NPC244776
0.9448	High Similarity	NPC105095
0.9448	High Similarity	NPC204937
0.9448	High Similarity	NPC79056
0.9448	High Similarity	NPC78734
0.9448	High Similarity	NPC116864
0.9448	High Similarity	NPC95866
0.9448	High Similarity	NPC149011

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 NPC475942 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	403
0.1-0.2	945
0.2-0.3	1927
0.3-0.4	2720
0.4-0.5	1786
0.5-0.6	902
0.6-0.7	293
0.7-0.8	134
0.8-0.85	13
0.85-0.9	16
0.9-0.95	10
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9632	High Similarity	NPD4338	Clinical (unspecified phase)
0.9627	High Similarity	NPD7054	Approved
0.9568	High Similarity	NPD7472	Approved
0.9448	High Similarity	NPD7074	Phase 3
0.9444	High Similarity	NPD3818	Discontinued
0.939	High Similarity	NPD6797	Phase 2
0.9333	High Similarity	NPD7251	Discontinued
0.9277	High Similarity	NPD7808	Phase 3
0.9241	High Similarity	NPD2801	Approved
0.9187	High Similarity	NPD4381	Clinical (unspecified phase)
0.9057	High Similarity	NPD1934	Approved
0.897	High Similarity	NPD6166	Phase 2
0.897	High Similarity	NPD6167	Clinical (unspecified phase)
0.897	High Similarity	NPD6168	Clinical (unspecified phase)
0.8882	High Similarity	NPD2393	Clinical (unspecified phase)
0.881	High Similarity	NPD7804	Clinical (unspecified phase)
0.8712	High Similarity	NPD3817	Phase 2
0.8671	High Similarity	NPD1511	Approved
0.8659	High Similarity	NPD4868	Clinical (unspecified phase)
0.8659	High Similarity	NPD3882	Suspended
0.858	High Similarity	NPD4380	Phase 2
0.8562	High Similarity	NPD1512	Approved
0.8503	High Similarity	NPD5494	Approved
0.8485	Intermediate Similarity	NPD5402	Approved
0.8457	Intermediate Similarity	NPD1653	Approved
0.8439	Intermediate Similarity	NPD6559	Discontinued
0.8276	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8274	Intermediate Similarity	NPD7075	Discontinued
0.8266	Intermediate Similarity	NPD5844	Phase 1
0.8176	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8176	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.816	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8144	Intermediate Similarity	NPD6801	Discontinued
0.8125	Intermediate Similarity	NPD7685	Pre-registration
0.8125	Intermediate Similarity	NPD1549	Phase 2
0.8122	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.8095	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8095	Intermediate Similarity	NPD1465	Phase 2
0.8081	Intermediate Similarity	NPD6232	Discontinued
0.8061	Intermediate Similarity	NPD5403	Approved
0.8047	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8046	Intermediate Similarity	NPD7473	Discontinued
0.8011	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD3751	Discontinued
0.8	Intermediate Similarity	NPD2796	Approved
0.8	Intermediate Similarity	NPD7228	Approved
0.7988	Intermediate Similarity	NPD7819	Suspended
0.7988	Intermediate Similarity	NPD6799	Approved
0.7977	Intermediate Similarity	NPD3787	Discontinued
0.7976	Intermediate Similarity	NPD7411	Suspended
0.7952	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7939	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7939	Intermediate Similarity	NPD5401	Approved
0.7937	Intermediate Similarity	NPD1510	Phase 2
0.7919	Intermediate Similarity	NPD7199	Phase 2
0.7919	Intermediate Similarity	NPD6959	Discontinued
0.7907	Intermediate Similarity	NPD6234	Discontinued
0.7845	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7833	Intermediate Similarity	NPD8313	Approved
0.7833	Intermediate Similarity	NPD8312	Approved
0.7824	Intermediate Similarity	NPD37	Approved
0.7819	Intermediate Similarity	NPD6780	Approved
0.7819	Intermediate Similarity	NPD6776	Approved
0.7819	Intermediate Similarity	NPD6779	Approved
0.7819	Intermediate Similarity	NPD6781	Approved
0.7819	Intermediate Similarity	NPD6777	Approved
0.7819	Intermediate Similarity	NPD6778	Approved
0.7819	Intermediate Similarity	NPD6782	Approved
0.7816	Intermediate Similarity	NPD1247	Approved
0.7805	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7799	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7799	Intermediate Similarity	NPD1613	Approved
0.7791	Intermediate Similarity	NPD4966	Approved
0.7791	Intermediate Similarity	NPD4965	Approved
0.7791	Intermediate Similarity	NPD4967	Phase 2
0.773	Intermediate Similarity	NPD7266	Discontinued
0.7727	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7706	Intermediate Similarity	NPD6599	Discontinued
0.7696	Intermediate Similarity	NPD7435	Discontinued
0.7688	Intermediate Similarity	NPD1240	Approved
0.7688	Intermediate Similarity	NPD943	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)
0.7651	Intermediate Similarity	NPD6190	Approved
0.764	Intermediate Similarity	NPD230	Phase 1
0.764	Intermediate Similarity	NPD1933	Approved
0.7627	Intermediate Similarity	NPD3926	Phase 2
0.761	Intermediate Similarity	NPD3027	Phase 3
0.7604	Intermediate Similarity	NPD7698	Approved
0.7604	Intermediate Similarity	NPD7696	Phase 3
0.7604	Intermediate Similarity	NPD7697	Approved
0.7602	Intermediate Similarity	NPD7783	Phase 2
0.7602	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.76	Intermediate Similarity	NPD919	Approved
0.7593	Intermediate Similarity	NPD1607	Approved
0.759	Intermediate Similarity	NPD8151	Discontinued
0.759	Intermediate Similarity	NPD3750	Approved
0.7565	Intermediate Similarity	NPD7870	Phase 2
0.7565	Intermediate Similarity	NPD7871	Phase 2
0.7561	Intermediate Similarity	NPD2935	Discontinued
0.7553	Intermediate Similarity	NPD6535	Approved
0.7553	Intermediate Similarity	NPD6534	Approved
0.7552	Intermediate Similarity	NPD6823	Phase 2
0.7547	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7543	Intermediate Similarity	NPD3749	Approved
0.7538	Intermediate Similarity	NPD7701	Phase 2
0.7531	Intermediate Similarity	NPD447	Suspended
0.7527	Intermediate Similarity	NPD7240	Approved
0.7486	Intermediate Similarity	NPD7768	Phase 2
0.7485	Intermediate Similarity	NPD4628	Phase 3
0.7484	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7471	Intermediate Similarity	NPD8455	Phase 2
0.7462	Intermediate Similarity	NPD7874	Approved
0.7462	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7455	Intermediate Similarity	NPD1551	Phase 2
0.7453	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7435	Intermediate Similarity	NPD7699	Phase 2
0.7435	Intermediate Similarity	NPD7700	Phase 2
0.7424	Intermediate Similarity	NPD7801	Approved
0.7414	Intermediate Similarity	NPD6844	Discontinued
0.7412	Intermediate Similarity	NPD2532	Approved
0.7412	Intermediate Similarity	NPD2534	Approved
0.7412	Intermediate Similarity	NPD2533	Approved
0.7358	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7326	Intermediate Similarity	NPD920	Approved
0.7321	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7321	Intermediate Similarity	NPD2800	Approved
0.7316	Intermediate Similarity	NPD6212	Phase 3
0.7316	Intermediate Similarity	NPD6213	Phase 3
0.7316	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.7292	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7289	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7289	Intermediate Similarity	NPD3748	Approved
0.7283	Intermediate Similarity	NPD5953	Discontinued
0.7273	Intermediate Similarity	NPD7585	Approved
0.7267	Intermediate Similarity	NPD9494	Approved
0.7241	Intermediate Similarity	NPD3226	Approved
0.7234	Intermediate Similarity	NPD8434	Phase 2
0.7234	Intermediate Similarity	NPD8150	Discontinued
0.7222	Intermediate Similarity	NPD7583	Approved
0.7219	Intermediate Similarity	NPD6674	Discontinued
0.7216	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7215	Intermediate Similarity	NPD1091	Approved
0.7209	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7209	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7204	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD4363	Phase 3
0.7188	Intermediate Similarity	NPD4360	Phase 2
0.7186	Intermediate Similarity	NPD7033	Discontinued
0.7174	Intermediate Similarity	NPD7286	Phase 2
0.7157	Intermediate Similarity	NPD7680	Approved
0.7143	Intermediate Similarity	NPD6099	Approved
0.7143	Intermediate Similarity	NPD7458	Discontinued
0.7143	Intermediate Similarity	NPD6100	Approved
0.7135	Intermediate Similarity	NPD5353	Approved
0.7134	Intermediate Similarity	NPD2313	Discontinued
0.7125	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7121	Intermediate Similarity	NPD8320	Phase 1
0.7121	Intermediate Similarity	NPD8319	Approved
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
0.7101	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD2346	Discontinued
0.7101	Intermediate Similarity	NPD2344	Approved
0.7099	Intermediate Similarity	NPD2798	Approved
0.7093	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD6233	Phase 2
0.7083	Intermediate Similarity	NPD2799	Discontinued
0.7066	Intermediate Similarity	NPD6651	Approved
0.7052	Intermediate Similarity	NPD7390	Discontinued
0.7049	Intermediate Similarity	NPD5242	Approved
0.7037	Intermediate Similarity	NPD1203	Approved
0.703	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD7549	Discontinued
0.702	Intermediate Similarity	NPD5006	Approved
0.702	Intermediate Similarity	NPD5005	Approved
0.7011	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7011	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
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	NPD7211	Clinical (unspecified phase)
0.6995	Remote Similarity	NPD5710	Approved
0.6995	Remote Similarity	NPD5711	Approved
0.6982	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD6386	Approved
0.6966	Remote Similarity	NPD6385	Approved
0.6966	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6962	Remote Similarity	NPD1548	Phase 1
0.6957	Remote Similarity	NPD9269	Phase 2
0.6952	Remote Similarity	NPD5619	Clinical (unspecified phase)
0.6951	Remote Similarity	NPD2861	Phase 2
0.6949	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6947	Remote Similarity	NPD7090	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