NPASS Compound

Structure

NPC471405 OpenBabel07101718192D 36 38 0 0 1 0 0 0 0 0999 V2000 2.5981 4.5000 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 4.3301 1.5000 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 -4.3301 1.5000 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 -6.0622 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 1.5000 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 -1.7321 0.0000 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 -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 -6.9282 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 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 2.5981 1.5000 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 -2.5981 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 -0.0000 -2.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8660 4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 -0.5000 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 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 1.5000 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 -1.7321 1.0000 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 0.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 13 1 0 0 0 0 2 32 1 0 0 0 0 3 33 1 0 0 0 0 4 7 2 0 0 0 0 4 14 1 0 0 0 0 5 9 2 0 0 0 0 5 14 1 0 0 0 0 6 8 2 0 0 0 0 6 15 1 0 0 0 0 7 16 1 0 0 0 0 8 17 1 0 0 0 0 9 21 1 0 0 0 0 10 14 2 0 0 0 0 10 18 1 0 0 0 0 11 15 2 0 0 0 0 11 19 1 0 0 0 0 12 34 1 0 0 0 0 13 15 1 0 0 0 0 13 26 2 0 0 0 0 16 18 2 0 0 0 0 16 27 1 0 0 0 0 17 19 2 0 0 0 0 17 35 1 0 0 0 0 18 32 1 0 0 0 0 19 33 1 0 0 0 0 20 12 1 1 0 0 0 20 22 1 0 0 0 0 20 36 1 0 0 0 0 21 28 2 0 0 0 0 21 34 1 0 0 0 0 22 23 1 0 0 0 0 22 29 1 6 0 0 0 23 24 1 0 0 0 0 23 30 1 1 0 0 0 24 25 1 0 0 0 0 24 31 1 6 0 0 0 25 35 1 1 0 0 0 25 36 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	504.16
Volume:	488.251
LogP:	1.742
LogD:	1.53
LogS:	-3.617
# Rotatable Bonds:	10
TPSA:	161.21
# H-Bond Aceptor:	11
# H-Bond Donor:	4
# Rings:	3
# Heavy Atoms:	11

MedChem Properties

QED Drug-Likeness Score:	0.219
Synthetic Accessibility Score:	3.735
Fsp3:	0.36
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.921
MDCK Permeability:	4.164017445873469e-05
Pgp-inhibitor:	0.193
Pgp-substrate:	0.347
Human Intestinal Absorption (HIA):	0.82
20% Bioavailability (F20%):	0.097
30% Bioavailability (F30%):	0.993

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.384
Plasma Protein Binding (PPB):	96.18038177490234%
Volume Distribution (VD):	0.417
Pgp-substrate:	6.068342685699463%

ADMET: Metabolism

CYP1A2-inhibitor:	0.148
CYP1A2-substrate:	0.628
CYP2C19-inhibitor:	0.2
CYP2C19-substrate:	0.341
CYP2C9-inhibitor:	0.482
CYP2C9-substrate:	0.81
CYP2D6-inhibitor:	0.129
CYP2D6-substrate:	0.641
CYP3A4-inhibitor:	0.202
CYP3A4-substrate:	0.205

ADMET: Excretion

Clearance (CL):	6.96
Half-life (T1/2):	0.925

ADMET: Toxicity

hERG Blockers:	0.293
Human Hepatotoxicity (H-HT):	0.133
Drug-inuced Liver Injury (DILI):	0.21
AMES Toxicity:	0.246
Rat Oral Acute Toxicity:	0.037
Maximum Recommended Daily Dose:	0.027
Skin Sensitization:	0.8
Carcinogencity:	0.286
Eye Corrosion:	0.003
Eye Irritation:	0.025
Respiratory Toxicity:	0.043

Download Data

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

Natural Product: NPC471405

Natural Product ID:	NPC471405
*Common Name:**	Scroneoside A
IUPAC Name:	[(2R,3S,4S,5R,6S)-6-(4-acetyl-2-methoxyphenoxy)-3,4,5-trihydroxyoxan-2-yl]methyl (E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate
Synonyms:
Standard InCHIKey:	MHPWKMWQIOIJHD-WDOAYHAPSA-N
Standard InCHI:	InChI=1S/C25H28O11/c1-13(26)15-6-8-17(19(11-15)33-3)35-25-24(31)23(30)22(29)20(36-25)12-34-21(28)9-5-14-4-7-16(27)18(10-14)32-2/h4-11,20,22-25,27,29-31H,12H2,1-3H3/b9-5+/t20-,22-,23+,24-,25-/m1/s1
SMILES:	COc1cc(ccc1O[C@@H]1O[C@H](COC(=O)/C=C/c2ccc(c(c2)OC)O)[C@H]([C@@H]([C@H]1O)O)O)C(=O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2436435
PubChem CID:	73347939
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0000011] Carbohydrates and carbohydrate conjugates [CHEMONTID:0002105] Glycosyl compounds [CHEMONTID:0004165] Phenolic 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
NPO30241	Picrorhiza scrophulariiflora	Species	Plantaginaceae	Eukaryota	n.a.	root	n.a.	PMID[15133218]
NPO30241	Picrorhiza scrophulariiflora	Species	Plantaginaceae	Eukaryota	n.a.	root	n.a.	PMID[15706916]
NPO30241	Picrorhiza scrophulariiflora	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24035096]
NPO30241	Picrorhiza scrophulariiflora	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO30241	Picrorhiza scrophulariiflora	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]

☑ 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
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	>	25000.0	nM	PMID[529909]

☑ 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 NPC471405 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	344
0.1-0.2	1444
0.2-0.3	3386
0.3-0.4	7693
0.4-0.5	10042
0.5-0.6	4591
0.6-0.7	5716
0.7-0.8	7130
0.8-0.85	1744
0.85-0.9	523
0.9-0.95	64
0.95-1	20

Similarity Score	Similarity Level	Natural Product ID
0.9932	High Similarity	NPC10205
0.9865	High Similarity	NPC191046
0.9865	High Similarity	NPC194095
0.9865	High Similarity	NPC327032
0.9797	High Similarity	NPC157898
0.9797	High Similarity	NPC137813
0.973	High Similarity	NPC134905
0.973	High Similarity	NPC36130
0.9671	High Similarity	NPC203020
0.9671	High Similarity	NPC239966
0.9669	High Similarity	NPC133984
0.9605	High Similarity	NPC160780
0.9605	High Similarity	NPC289811
0.9595	High Similarity	NPC205054
0.9539	High Similarity	NPC226759
0.9539	High Similarity	NPC472860
0.9539	High Similarity	NPC1913
0.9527	High Similarity	NPC111785
0.9527	High Similarity	NPC98809
0.9527	High Similarity	NPC476394
0.9481	High Similarity	NPC311803
0.9481	High Similarity	NPC472859
0.9481	High Similarity	NPC25389
0.9459	High Similarity	NPC472969
0.9427	High Similarity	NPC116745
0.9419	High Similarity	NPC285108
0.9419	High Similarity	NPC33298
0.9416	High Similarity	NPC166277
0.9416	High Similarity	NPC119125
0.9351	High Similarity	NPC74319
0.9351	High Similarity	NPC287872
0.9324	High Similarity	NPC291153
0.9295	High Similarity	NPC148273
0.929	High Similarity	NPC289346
0.9276	High Similarity	NPC310661
0.9276	High Similarity	NPC105827
0.9267	High Similarity	NPC478242
0.9236	High Similarity	NPC88043
0.9211	High Similarity	NPC75695
0.9193	High Similarity	NPC88560
0.9193	High Similarity	NPC175230
0.9193	High Similarity	NPC172033
0.9189	High Similarity	NPC473090
0.9187	High Similarity	NPC204937
0.9187	High Similarity	NPC149011
0.9177	High Similarity	NPC165720
0.9172	High Similarity	NPC90905
0.9172	High Similarity	NPC4013
0.915	High Similarity	NPC44730
0.9145	High Similarity	NPC140151
0.913	High Similarity	NPC172807
0.913	High Similarity	NPC211594
0.913	High Similarity	NPC254540
0.9125	High Similarity	NPC658
0.9125	High Similarity	NPC229687
0.9125	High Similarity	NPC197708
0.9122	High Similarity	NPC478239
0.9085	High Similarity	NPC289438
0.9079	High Similarity	NPC473091
0.9074	High Similarity	NPC4390
0.9074	High Similarity	NPC316539
0.9074	High Similarity	NPC472993
0.9068	High Similarity	NPC212748
0.9067	High Similarity	NPC287495
0.9067	High Similarity	NPC9370
0.9062	High Similarity	NPC229729
0.9062	High Similarity	NPC45400
0.9062	High Similarity	NPC298847
0.9057	High Similarity	NPC180586
0.9057	High Similarity	NPC22832
0.9057	High Similarity	NPC311830
0.9054	High Similarity	NPC140502
0.9054	High Similarity	NPC157816
0.9051	High Similarity	NPC41009
0.9051	High Similarity	NPC127782
0.9051	High Similarity	NPC300537
0.9045	High Similarity	NPC44507
0.9038	High Similarity	NPC40920
0.9038	High Similarity	NPC223335
0.9026	High Similarity	NPC245615
0.9026	High Similarity	NPC61604
0.9026	High Similarity	NPC299706
0.9026	High Similarity	NPC115466
0.9024	High Similarity	NPC267549
0.9018	High Similarity	NPC477848
0.9013	High Similarity	NPC92117
0.9012	High Similarity	NPC472386
0.9012	High Similarity	NPC307518
0.9012	High Similarity	NPC190003
0.9012	High Similarity	NPC102851
0.9012	High Similarity	NPC153755
0.9012	High Similarity	NPC175107
0.9012	High Similarity	NPC48773
0.9012	High Similarity	NPC5786
0.9012	High Similarity	NPC205076
0.9006	High Similarity	NPC105025
0.9006	High Similarity	NPC475942
0.9006	High Similarity	NPC469931
0.9006	High Similarity	NPC45638
0.9006	High Similarity	NPC58053
0.9006	High Similarity	NPC93337
0.9006	High Similarity	NPC226294
0.9006	High Similarity	NPC186807
0.9006	High Similarity	NPC201292
0.9	High Similarity	NPC236934
0.9	High Similarity	NPC5778
0.8994	High Similarity	NPC147596
0.8994	High Similarity	NPC243930
0.8994	High Similarity	NPC222936
0.8994	High Similarity	NPC191306
0.8994	High Similarity	NPC284960
0.8994	High Similarity	NPC19709
0.8994	High Similarity	NPC168822
0.8994	High Similarity	NPC88023
0.8994	High Similarity	NPC270335
0.8994	High Similarity	NPC309025
0.8986	High Similarity	NPC186406
0.8986	High Similarity	NPC326065
0.8981	High Similarity	NPC469654
0.8968	High Similarity	NPC469888
0.8963	High Similarity	NPC472991
0.8963	High Similarity	NPC472992
0.8963	High Similarity	NPC233994
0.8963	High Similarity	NPC67629
0.8963	High Similarity	NPC79736
0.8963	High Similarity	NPC472385
0.8963	High Similarity	NPC211532
0.8963	High Similarity	NPC198324
0.8957	High Similarity	NPC163165
0.8954	High Similarity	NPC227980
0.8954	High Similarity	NPC182350
0.8951	High Similarity	NPC72249
0.8951	High Similarity	NPC155763
0.8951	High Similarity	NPC105511
0.8951	High Similarity	NPC51326
0.8951	High Similarity	NPC21190
0.8951	High Similarity	NPC224462
0.8951	High Similarity	NPC183357
0.8951	High Similarity	NPC22195
0.8951	High Similarity	NPC235260
0.8951	High Similarity	NPC34287
0.8951	High Similarity	NPC206123
0.8951	High Similarity	NPC244776
0.8951	High Similarity	NPC474434
0.8951	High Similarity	NPC116864
0.8951	High Similarity	NPC471416
0.8951	High Similarity	NPC20505
0.8951	High Similarity	NPC231194
0.8951	High Similarity	NPC44558
0.8947	High Similarity	NPC248257
0.8947	High Similarity	NPC120621
0.8947	High Similarity	NPC116229
0.8944	High Similarity	NPC45618
0.8944	High Similarity	NPC146792
0.8944	High Similarity	NPC58716
0.894	High Similarity	NPC199928
0.894	High Similarity	NPC473867
0.8938	High Similarity	NPC475738
0.8933	High Similarity	NPC232228
0.8931	High Similarity	NPC77660
0.8931	High Similarity	NPC61594
0.8931	High Similarity	NPC189142
0.8931	High Similarity	NPC473043
0.8931	High Similarity	NPC476011
0.8931	High Similarity	NPC22324
0.8931	High Similarity	NPC56735
0.8924	High Similarity	NPC53889
0.891	High Similarity	NPC131532
0.8909	High Similarity	NPC472387
0.8909	High Similarity	NPC476620
0.8909	High Similarity	NPC476623
0.8909	High Similarity	NPC476622
0.8909	High Similarity	NPC217520
0.8909	High Similarity	NPC35167
0.8909	High Similarity	NPC476621
0.8909	High Similarity	NPC476618
0.8909	High Similarity	NPC476619
0.8909	High Similarity	NPC139571
0.8902	High Similarity	NPC210094
0.8902	High Similarity	NPC43211
0.8902	High Similarity	NPC49344
0.8902	High Similarity	NPC169645
0.8902	High Similarity	NPC84482
0.8902	High Similarity	NPC237435
0.8902	High Similarity	NPC115760
0.8902	High Similarity	NPC135277
0.8902	High Similarity	NPC264735
0.8902	High Similarity	NPC101191
0.8896	High Similarity	NPC243891
0.8896	High Similarity	NPC476405
0.8896	High Similarity	NPC47140
0.8896	High Similarity	NPC67134
0.8896	High Similarity	NPC235575
0.8896	High Similarity	NPC117260
0.8889	High Similarity	NPC95421
0.8889	High Similarity	NPC170675
0.8889	High Similarity	NPC203050
0.8889	High Similarity	NPC209296
0.8889	High Similarity	NPC471457
0.8889	High Similarity	NPC95855

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 NPC471405 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	295
0.1-0.2	851
0.2-0.3	1722
0.3-0.4	2529
0.4-0.5	1986
0.5-0.6	1066
0.6-0.7	524
0.7-0.8	146
0.8-0.85	24
0.85-0.9	7
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8944	High Similarity	NPD3818	Discontinued
0.8902	High Similarity	NPD4338	Clinical (unspecified phase)
0.8889	High Similarity	NPD7054	Approved
0.8834	High Similarity	NPD7472	Approved
0.8834	High Similarity	NPD7074	Phase 3
0.8734	High Similarity	NPD4868	Clinical (unspecified phase)
0.8727	High Similarity	NPD7685	Pre-registration
0.8667	High Similarity	NPD6797	Phase 2
0.8614	High Similarity	NPD7251	Discontinued
0.8563	High Similarity	NPD7808	Phase 3
0.8562	High Similarity	NPD4381	Clinical (unspecified phase)
0.8544	High Similarity	NPD1934	Approved
0.8477	Intermediate Similarity	NPD7266	Discontinued
0.8387	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.8375	Intermediate Similarity	NPD2801	Approved
0.8375	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8364	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8364	Intermediate Similarity	NPD6166	Phase 2
0.8364	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8344	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.8333	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8323	Intermediate Similarity	NPD3817	Phase 2
0.8312	Intermediate Similarity	NPD4628	Phase 3
0.8291	Intermediate Similarity	NPD1653	Approved
0.8272	Intermediate Similarity	NPD3882	Suspended
0.8258	Intermediate Similarity	NPD6190	Approved
0.8198	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.8176	Intermediate Similarity	NPD6559	Discontinued
0.8148	Intermediate Similarity	NPD1465	Phase 2
0.811	Intermediate Similarity	NPD7075	Discontinued
0.8107	Intermediate Similarity	NPD5844	Phase 1
0.8107	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8061	Intermediate Similarity	NPD6234	Discontinued
0.8047	Intermediate Similarity	NPD7228	Approved
0.8038	Intermediate Similarity	NPD1511	Approved
0.8026	Intermediate Similarity	NPD230	Phase 1
0.7977	Intermediate Similarity	NPD8313	Approved
0.7977	Intermediate Similarity	NPD8312	Approved
0.7975	Intermediate Similarity	NPD37	Approved
0.7964	Intermediate Similarity	NPD7199	Phase 2
0.7963	Intermediate Similarity	NPD4380	Phase 2
0.7955	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7939	Intermediate Similarity	NPD4965	Approved
0.7939	Intermediate Similarity	NPD4966	Approved
0.7939	Intermediate Similarity	NPD4967	Phase 2
0.7937	Intermediate Similarity	NPD1512	Approved
0.7927	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7898	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7879	Intermediate Similarity	NPD5402	Approved
0.7867	Intermediate Similarity	NPD9494	Approved
0.7866	Intermediate Similarity	NPD6801	Discontinued
0.7865	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7818	Intermediate Similarity	NPD8455	Phase 2
0.7818	Intermediate Similarity	NPD7819	Suspended
0.7812	Intermediate Similarity	NPD6799	Approved
0.7811	Intermediate Similarity	NPD6232	Discontinued
0.7798	Intermediate Similarity	NPD5494	Approved
0.7792	Intermediate Similarity	NPD1933	Approved
0.7778	Intermediate Similarity	NPD7473	Discontinued
0.7765	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7722	Intermediate Similarity	NPD1549	Phase 2
0.7718	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7697	Intermediate Similarity	NPD6386	Approved
0.7697	Intermediate Similarity	NPD7411	Suspended
0.7697	Intermediate Similarity	NPD6385	Approved
0.7677	Intermediate Similarity	NPD447	Suspended
0.7669	Intermediate Similarity	NPD5403	Approved
0.7658	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7658	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD3027	Phase 3
0.763	Intermediate Similarity	NPD3751	Discontinued
0.7613	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7613	Intermediate Similarity	NPD1613	Approved
0.7576	Intermediate Similarity	NPD7458	Discontinued
0.7557	Intermediate Similarity	NPD7038	Approved
0.7557	Intermediate Similarity	NPD7240	Approved
0.7557	Intermediate Similarity	NPD7039	Approved
0.7548	Intermediate Similarity	NPD6233	Phase 2
0.7546	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7546	Intermediate Similarity	NPD5401	Approved
0.753	Intermediate Similarity	NPD6599	Discontinued
0.7516	Intermediate Similarity	NPD3750	Approved
0.7516	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD3787	Discontinued
0.7484	Intermediate Similarity	NPD2796	Approved
0.7484	Intermediate Similarity	NPD2935	Discontinued
0.7484	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.747	Intermediate Similarity	NPD3226	Approved
0.7456	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7456	Intermediate Similarity	NPD5353	Approved
0.7447	Intermediate Similarity	NPD7435	Discontinued
0.7444	Intermediate Similarity	NPD8434	Phase 2
0.7442	Intermediate Similarity	NPD8127	Discontinued
0.7439	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7432	Intermediate Similarity	NPD9545	Approved
0.7421	Intermediate Similarity	NPD1510	Phase 2
0.7417	Intermediate Similarity	NPD1608	Approved
0.7414	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.738	Intermediate Similarity	NPD6779	Approved
0.738	Intermediate Similarity	NPD6780	Approved
0.738	Intermediate Similarity	NPD6781	Approved
0.738	Intermediate Similarity	NPD6782	Approved
0.738	Intermediate Similarity	NPD6778	Approved
0.738	Intermediate Similarity	NPD6777	Approved
0.738	Intermediate Similarity	NPD6776	Approved
0.7372	Intermediate Similarity	NPD6798	Discontinued
0.7365	Intermediate Similarity	NPD3455	Phase 2
0.7356	Intermediate Similarity	NPD5242	Approved
0.7355	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7351	Intermediate Similarity	NPD1091	Approved
0.7346	Intermediate Similarity	NPD6674	Discontinued
0.7344	Intermediate Similarity	NPD8151	Discontinued
0.7341	Intermediate Similarity	NPD6959	Discontinued
0.7333	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD2346	Discontinued
0.7326	Intermediate Similarity	NPD919	Approved
0.7312	Intermediate Similarity	NPD2799	Discontinued
0.7312	Intermediate Similarity	NPD7033	Discontinued
0.7303	Intermediate Similarity	NPD9269	Phase 2
0.7301	Intermediate Similarity	NPD4110	Phase 3
0.7301	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.729	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7289	Intermediate Similarity	NPD6273	Approved
0.7284	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD943	Approved
0.7278	Intermediate Similarity	NPD1240	Approved
0.7268	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7268	Intermediate Similarity	NPD7783	Phase 2
0.7267	Intermediate Similarity	NPD1551	Phase 2
0.7267	Intermediate Similarity	NPD3749	Approved
0.7262	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7261	Intermediate Similarity	NPD2313	Discontinued
0.7261	Intermediate Similarity	NPD3764	Approved
0.7257	Intermediate Similarity	NPD3926	Phase 2
0.7256	Intermediate Similarity	NPD2354	Approved
0.7256	Intermediate Similarity	NPD3887	Approved
0.725	Intermediate Similarity	NPD7097	Phase 1
0.7248	Intermediate Similarity	NPD5536	Phase 2
0.7244	Intermediate Similarity	NPD6832	Phase 2
0.7234	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7233	Intermediate Similarity	NPD6355	Discontinued
0.7219	Intermediate Similarity	NPD17	Approved
0.7216	Intermediate Similarity	NPD7874	Approved
0.7216	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7215	Intermediate Similarity	NPD4062	Phase 3
0.7209	Intermediate Similarity	NPD7768	Phase 2
0.7205	Intermediate Similarity	NPD3748	Approved
0.7202	Intermediate Similarity	NPD7585	Approved
0.7195	Intermediate Similarity	NPD8166	Discontinued
0.7188	Intermediate Similarity	NPD1607	Approved
0.7173	Intermediate Similarity	NPD7698	Approved
0.7173	Intermediate Similarity	NPD7697	Approved
0.7173	Intermediate Similarity	NPD7680	Approved
0.7173	Intermediate Similarity	NPD7696	Phase 3
0.7161	Intermediate Similarity	NPD1203	Approved
0.7158	Intermediate Similarity	NPD8150	Discontinued
0.7152	Intermediate Similarity	NPD3268	Approved
0.715	Intermediate Similarity	NPD7583	Approved
0.715	Intermediate Similarity	NPD7584	Approved
0.7143	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD1247	Approved
0.7135	Intermediate Similarity	NPD7871	Phase 2
0.7135	Intermediate Similarity	NPD7870	Phase 2
0.7129	Intermediate Similarity	NPD5619	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD2532	Approved
0.7126	Intermediate Similarity	NPD2534	Approved
0.7126	Intermediate Similarity	NPD2533	Approved
0.7126	Intermediate Similarity	NPD3688	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD3146	Approved
0.7125	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7124	Intermediate Similarity	NPD3705	Approved
0.712	Intermediate Similarity	NPD6823	Phase 2
0.7117	Intermediate Similarity	NPD2344	Approved
0.7113	Intermediate Similarity	NPD7701	Phase 2
0.7112	Intermediate Similarity	NPD6534	Approved
0.7112	Intermediate Similarity	NPD6535	Approved
0.7111	Intermediate Similarity	NPD5953	Discontinued
0.7108	Intermediate Similarity	NPD7440	Discontinued
0.7099	Intermediate Similarity	NPD4308	Phase 3
0.7091	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD7095	Approved
0.7081	Intermediate Similarity	NPD6653	Approved
0.7078	Intermediate Similarity	NPD1481	Phase 2
0.7063	Intermediate Similarity	NPD4060	Phase 1
0.7051	Intermediate Similarity	NPD2797	Approved
0.7047	Intermediate Similarity	NPD8319	Approved
0.7047	Intermediate Similarity	NPD8320	Phase 1
0.7041	Intermediate Similarity	NPD920	Approved
0.7039	Intermediate Similarity	NPD1357	Approved
0.7039	Intermediate Similarity	NPD9268	Approved
0.7039	Intermediate Similarity	NPD2163	Approved
0.7035	Intermediate Similarity	NPD6844	Discontinued
0.703	Intermediate Similarity	NPD1652	Phase 2
0.7019	Intermediate Similarity	NPD4340	Discontinued
0.7018	Intermediate Similarity	NPD7028	Phase 2
0.7016	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7013	Intermediate Similarity	NPD1535	Discovery
0.7013	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7012	Intermediate Similarity	NPD2353	Approved
0.7012	Intermediate Similarity	NPD2343	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