NPASS Compound

Structure

CID135370 OpenBabel06191715492D 35 39 0 0 1 0 0 0 0 0999 V2000 5.1962 6.0000 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 2.5981 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.2350 4.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.2350 4.3660 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 4.3301 2.5000 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 8.2350 2.6340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1472 2.6910 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 10.8177 2.2976 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 7.7350 3.5000 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 9.7350 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7350 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.2350 2.6340 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 -0.8660 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 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 5.1962 4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 0.0000 C 0 0 2 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 -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 4.3301 5.5000 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 10.7131 3.2921 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 9.9041 1.8908 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.1472 4.3090 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 30 1 0 0 0 0 2 3 1 0 0 0 0 2 6 1 0 0 0 0 3 13 1 0 0 0 0 4 5 2 0 0 0 0 4 14 1 0 0 0 0 5 16 1 0 0 0 0 6 31 1 0 0 0 0 7 13 2 0 0 0 0 7 15 1 0 0 0 0 8 13 1 0 0 0 0 8 19 2 0 0 0 0 9 14 2 0 0 0 0 9 18 1 0 0 0 0 10 15 1 0 0 0 0 10 17 2 0 0 0 0 11 26 1 0 0 0 0 12 32 1 0 0 0 0 12 33 1 0 0 0 0 14 17 1 0 0 0 0 15 24 2 0 0 0 0 16 18 2 0 0 0 0 16 32 1 0 0 0 0 17 34 1 0 0 0 0 18 33 1 0 0 0 0 19 24 1 0 0 0 0 19 30 1 0 0 0 0 20 11 1 6 0 0 0 20 21 1 0 0 0 0 20 35 1 0 0 0 0 21 22 1 0 0 0 0 21 27 1 1 0 0 0 22 23 1 0 0 0 0 22 28 1 6 0 0 0 23 25 1 0 0 0 0 23 29 1 1 0 0 0 24 34 1 0 0 0 0 25 31 1 6 0 0 0 25 35 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	488.17
Volume:	467.621
LogP:	2.782
LogD:	2.939
LogS:	-4.425
# Rotatable Bonds:	8
TPSA:	140.21
# H-Bond Aceptor:	10
# H-Bond Donor:	4
# Rings:	5
# Heavy Atoms:	10

MedChem Properties

QED Drug-Likeness Score:	0.346
Synthetic Accessibility Score:	3.906
Fsp3:	0.44
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.222
MDCK Permeability:	4.8254409193759784e-05
Pgp-inhibitor:	0.03
Pgp-substrate:	0.692
Human Intestinal Absorption (HIA):	0.009
20% Bioavailability (F20%):	0.008
30% Bioavailability (F30%):	0.029

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.089
Plasma Protein Binding (PPB):	94.60104370117188%
Volume Distribution (VD):	0.717
Pgp-substrate:	4.376323699951172%

ADMET: Metabolism

CYP1A2-inhibitor:	0.545
CYP1A2-substrate:	0.557
CYP2C19-inhibitor:	0.222
CYP2C19-substrate:	0.1
CYP2C9-inhibitor:	0.341
CYP2C9-substrate:	0.347
CYP2D6-inhibitor:	0.858
CYP2D6-substrate:	0.588
CYP3A4-inhibitor:	0.902
CYP3A4-substrate:	0.135

ADMET: Excretion

Clearance (CL):	11.464
Half-life (T1/2):	0.427

ADMET: Toxicity

hERG Blockers:	0.11
Human Hepatotoxicity (H-HT):	0.307
Drug-inuced Liver Injury (DILI):	0.843
AMES Toxicity:	0.8
Rat Oral Acute Toxicity:	0.052
Maximum Recommended Daily Dose:	0.285
Skin Sensitization:	0.202
Carcinogencity:	0.847
Eye Corrosion:	0.003
Eye Irritation:	0.011
Respiratory Toxicity:	0.041

Download Data

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

Natural Product: NPC135370

Natural Product ID:	NPC135370
*Common Name:**	Egonol Glucoside
IUPAC Name:	(2R,3R,4S,5S,6R)-2-[3-[2-(1,3-benzodioxol-5-yl)-7-methoxy-1-benzofuran-5-yl]propoxy]-6-(hydroxymethyl)oxane-3,4,5-triol
Synonyms:	Egonol Glucoside
Standard InCHIKey:	RAMYDZNQLYKTGB-MXCHMSEPSA-N
Standard InCHI:	InChI=1S/C25H28O10/c1-30-19-8-13(3-2-6-31-25-23(29)22(28)21(27)20(11-26)35-25)7-15-10-17(34-24(15)19)14-4-5-16-18(9-14)33-12-32-16/h4-5,7-10,20-23,25-29H,2-3,6,11-12H2,1H3/t20-,21-,22+,23-,25-/m1/s1
SMILES:	OC[C@H]1O[C@@H](OCCCc2cc(OC)c3c(c2)cc(o3)c2ccc3c(c2)OCO3)[C@@H]([C@H]([C@@H]1O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL470983
PubChem CID:	485187
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0003405] 2-arylbenzofuran flavonoids

*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
NPO17951	Styrax japonicus	Species	Styracaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8498.1	Laetiporus sulphureus var. miniatus	Varieties	Coriolaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8498.1	Laetiporus sulphureus var. miniatus	Varieties	Coriolaceae	Eukaryota	n.a.	n.a.	n.a.	Database[Title]
NPO17951	Styrax japonicus	Species	Styracaceae	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
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	24.9	ug.mL-1	PMID[485941]

☑ 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 NPC135370 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	400
0.1-0.2	1591
0.2-0.3	3400
0.3-0.4	8574
0.4-0.5	9952
0.5-0.6	4575
0.6-0.7	6369
0.7-0.8	6438
0.8-0.85	1083
0.85-0.9	313
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.956	High Similarity	NPC99968
0.9308	High Similarity	NPC261090
0.9245	High Similarity	NPC3273
0.9193	High Similarity	NPC15764
0.9141	High Similarity	NPC19948
0.9136	High Similarity	NPC139876
0.9119	High Similarity	NPC60211
0.908	High Similarity	NPC309335
0.908	High Similarity	NPC296540
0.8963	High Similarity	NPC109238
0.8951	High Similarity	NPC261484
0.8896	High Similarity	NPC82733
0.8896	High Similarity	NPC76458
0.8889	High Similarity	NPC268008
0.8889	High Similarity	NPC47191
0.8882	High Similarity	NPC137813
0.8876	High Similarity	NPC471920
0.8876	High Similarity	NPC20114
0.8876	High Similarity	NPC312006
0.8876	High Similarity	NPC471921
0.8876	High Similarity	NPC114550
0.8876	High Similarity	NPC129930
0.8876	High Similarity	NPC471922
0.8876	High Similarity	NPC474075
0.8876	High Similarity	NPC292712
0.8824	High Similarity	NPC316539
0.8817	High Similarity	NPC72249
0.8773	High Similarity	NPC10205
0.8772	High Similarity	NPC193377
0.872	High Similarity	NPC471405
0.8713	High Similarity	NPC184624
0.8713	High Similarity	NPC62640
0.8706	High Similarity	NPC212748
0.8706	High Similarity	NPC52598
0.8704	High Similarity	NPC36130
0.8704	High Similarity	NPC134905
0.8698	High Similarity	NPC48640
0.8698	High Similarity	NPC149244
0.8696	High Similarity	NPC88886
0.8696	High Similarity	NPC104172
0.8683	High Similarity	NPC125991
0.8675	High Similarity	NPC472961
0.8675	High Similarity	NPC472962
0.8671	High Similarity	NPC35266
0.8671	High Similarity	NPC168584
0.8671	High Similarity	NPC267549
0.8655	High Similarity	NPC157522
0.8647	High Similarity	NPC211309
0.8644	High Similarity	NPC205721
0.8639	High Similarity	NPC119589
0.8639	High Similarity	NPC113093
0.8621	High Similarity	NPC161609
0.8621	High Similarity	NPC275690
0.8613	High Similarity	NPC67629
0.8613	High Similarity	NPC79736
0.8613	High Similarity	NPC156635
0.8605	High Similarity	NPC199357
0.8598	High Similarity	NPC327032
0.8598	High Similarity	NPC191046
0.8598	High Similarity	NPC194095
0.8596	High Similarity	NPC206123
0.8588	High Similarity	NPC73703
0.8588	High Similarity	NPC186392
0.8588	High Similarity	NPC135345
0.858	High Similarity	NPC205054
0.858	High Similarity	NPC187923
0.858	High Similarity	NPC227980
0.858	High Similarity	NPC165720
0.8571	High Similarity	NPC148273
0.8562	High Similarity	NPC474044
0.8555	High Similarity	NPC469601
0.8555	High Similarity	NPC472607
0.8555	High Similarity	NPC294629
0.8555	High Similarity	NPC108202
0.8554	High Similarity	NPC133984
0.8554	High Similarity	NPC226759
0.8547	High Similarity	NPC235575
0.8547	High Similarity	NPC245452
0.8538	High Similarity	NPC270578
0.8538	High Similarity	NPC223747
0.8538	High Similarity	NPC61791
0.8538	High Similarity	NPC120099
0.8538	High Similarity	NPC219904
0.8538	High Similarity	NPC476771
0.8538	High Similarity	NPC225434
0.8538	High Similarity	NPC41853
0.8538	High Similarity	NPC203050
0.8538	High Similarity	NPC52382
0.8538	High Similarity	NPC229687
0.8537	High Similarity	NPC157898
0.8537	High Similarity	NPC44730
0.8529	High Similarity	NPC254306
0.8529	High Similarity	NPC471923
0.8529	High Similarity	NPC67037
0.8529	High Similarity	NPC255615
0.8523	High Similarity	NPC473883
0.8521	High Similarity	NPC100425
0.8521	High Similarity	NPC88043
0.8519	High Similarity	NPC111785
0.8514	High Similarity	NPC183843
0.8512	High Similarity	NPC182045
0.8506	High Similarity	NPC472384
0.8506	High Similarity	NPC154741
0.8506	High Similarity	NPC296018
0.8506	High Similarity	NPC472380
0.8506	High Similarity	NPC472382
0.8497	Intermediate Similarity	NPC45522
0.8497	Intermediate Similarity	NPC42773
0.8497	Intermediate Similarity	NPC169977
0.8497	Intermediate Similarity	NPC4390
0.8497	Intermediate Similarity	NPC21666
0.8497	Intermediate Similarity	NPC101026
0.8497	Intermediate Similarity	NPC24043
0.8494	Intermediate Similarity	NPC155063
0.8488	Intermediate Similarity	NPC105511
0.8488	Intermediate Similarity	NPC44558
0.8483	Intermediate Similarity	NPC475360
0.848	Intermediate Similarity	NPC325555
0.848	Intermediate Similarity	NPC473531
0.848	Intermediate Similarity	NPC127546
0.848	Intermediate Similarity	NPC223424
0.848	Intermediate Similarity	NPC477502
0.848	Intermediate Similarity	NPC116745
0.848	Intermediate Similarity	NPC476459
0.848	Intermediate Similarity	NPC167479
0.848	Intermediate Similarity	NPC160156
0.848	Intermediate Similarity	NPC84362
0.848	Intermediate Similarity	NPC265530
0.848	Intermediate Similarity	NPC92565
0.848	Intermediate Similarity	NPC229729
0.848	Intermediate Similarity	NPC173637
0.848	Intermediate Similarity	NPC317489
0.848	Intermediate Similarity	NPC52550
0.848	Intermediate Similarity	NPC475453
0.848	Intermediate Similarity	NPC226304
0.848	Intermediate Similarity	NPC42892
0.848	Intermediate Similarity	NPC45400
0.8475	Intermediate Similarity	NPC167045
0.8475	Intermediate Similarity	NPC148710
0.8475	Intermediate Similarity	NPC114120
0.8471	Intermediate Similarity	NPC300053
0.8471	Intermediate Similarity	NPC34531
0.8466	Intermediate Similarity	NPC208797
0.8466	Intermediate Similarity	NPC53680
0.8466	Intermediate Similarity	NPC473073
0.8466	Intermediate Similarity	NPC473071
0.8462	Intermediate Similarity	NPC61594
0.8462	Intermediate Similarity	NPC272722
0.8462	Intermediate Similarity	NPC56735
0.8462	Intermediate Similarity	NPC300537
0.8462	Intermediate Similarity	NPC127782
0.8457	Intermediate Similarity	NPC35167
0.8457	Intermediate Similarity	NPC476773
0.8457	Intermediate Similarity	NPC139571
0.8457	Intermediate Similarity	NPC67302
0.8457	Intermediate Similarity	NPC241196
0.8457	Intermediate Similarity	NPC217520
0.8457	Intermediate Similarity	NPC477895
0.8457	Intermediate Similarity	NPC469600
0.8452	Intermediate Similarity	NPC306978
0.8452	Intermediate Similarity	NPC110349
0.8452	Intermediate Similarity	NPC65784
0.8452	Intermediate Similarity	NPC203020
0.8452	Intermediate Similarity	NPC239966
0.8448	Intermediate Similarity	NPC264735
0.8448	Intermediate Similarity	NPC66804
0.8448	Intermediate Similarity	NPC146803
0.8448	Intermediate Similarity	NPC186800
0.8448	Intermediate Similarity	NPC470667
0.8443	Intermediate Similarity	NPC40920
0.8443	Intermediate Similarity	NPC223335
0.8439	Intermediate Similarity	NPC476772
0.8439	Intermediate Similarity	NPC307518
0.8439	Intermediate Similarity	NPC38438
0.8439	Intermediate Similarity	NPC153755
0.8439	Intermediate Similarity	NPC476405
0.8439	Intermediate Similarity	NPC175107
0.8439	Intermediate Similarity	NPC475155
0.8439	Intermediate Similarity	NPC256760
0.8439	Intermediate Similarity	NPC261254
0.8439	Intermediate Similarity	NPC205076
0.8439	Intermediate Similarity	NPC48773
0.8439	Intermediate Similarity	NPC121333
0.8439	Intermediate Similarity	NPC117260
0.8439	Intermediate Similarity	NPC190003
0.8434	Intermediate Similarity	NPC300757
0.8434	Intermediate Similarity	NPC180901
0.843	Intermediate Similarity	NPC472383
0.843	Intermediate Similarity	NPC472381
0.8421	Intermediate Similarity	NPC308404
0.8421	Intermediate Similarity	NPC5778
0.8421	Intermediate Similarity	NPC274618
0.8421	Intermediate Similarity	NPC179950
0.8421	Intermediate Similarity	NPC253662
0.8421	Intermediate Similarity	NPC145038
0.8421	Intermediate Similarity	NPC197285
0.8421	Intermediate Similarity	NPC113968
0.8421	Intermediate Similarity	NPC118284
0.8421	Intermediate Similarity	NPC277174
0.8421	Intermediate Similarity	NPC135599

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 NPC135370 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	340
0.1-0.2	879
0.2-0.3	1695
0.3-0.4	2686
0.4-0.5	2002
0.5-0.6	1014
0.6-0.7	402
0.7-0.8	114
0.8-0.85	12
0.85-0.9	6
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8588	High Similarity	NPD3818	Discontinued
0.8497	Intermediate Similarity	NPD6559	Discontinued
0.8343	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8343	Intermediate Similarity	NPD7808	Phase 3
0.8333	Intermediate Similarity	NPD6797	Phase 2
0.8286	Intermediate Similarity	NPD7251	Discontinued
0.8276	Intermediate Similarity	NPD7074	Phase 3
0.8218	Intermediate Similarity	NPD7054	Approved
0.8218	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8171	Intermediate Similarity	NPD7472	Approved
0.8166	Intermediate Similarity	NPD3882	Suspended
0.815	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.815	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.815	Intermediate Similarity	NPD6166	Phase 2
0.8118	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8107	Intermediate Similarity	NPD3817	Phase 2
0.8092	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.8059	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8049	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.8047	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8047	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8023	Intermediate Similarity	NPD5494	Approved
0.8012	Intermediate Similarity	NPD7075	Discontinued
0.8012	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.8011	Intermediate Similarity	NPD5844	Phase 1
0.8	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7988	Intermediate Similarity	NPD1934	Approved
0.7977	Intermediate Similarity	NPD1247	Approved
0.7977	Intermediate Similarity	NPD7199	Phase 2
0.7965	Intermediate Similarity	NPD919	Approved
0.7921	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7886	Intermediate Similarity	NPD3926	Phase 2
0.7882	Intermediate Similarity	NPD6801	Discontinued
0.7849	Intermediate Similarity	NPD4966	Approved
0.7849	Intermediate Similarity	NPD4965	Approved
0.7849	Intermediate Similarity	NPD4967	Phase 2
0.7836	Intermediate Similarity	NPD8455	Phase 2
0.7784	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD7685	Pre-registration
0.7765	Intermediate Similarity	NPD4380	Phase 2
0.7759	Intermediate Similarity	NPD6234	Discontinued
0.7753	Intermediate Similarity	NPD7228	Approved
0.7733	Intermediate Similarity	NPD2801	Approved
0.7697	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD8313	Approved
0.7692	Intermediate Similarity	NPD8312	Approved
0.7676	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7674	Intermediate Similarity	NPD37	Approved
0.7654	Intermediate Similarity	NPD3751	Discontinued
0.763	Intermediate Similarity	NPD7819	Suspended
0.7627	Intermediate Similarity	NPD3787	Discontinued
0.7627	Intermediate Similarity	NPD6232	Discontinued
0.7619	Intermediate Similarity	NPD6799	Approved
0.7598	Intermediate Similarity	NPD7473	Discontinued
0.7586	Intermediate Similarity	NPD5402	Approved
0.7582	Intermediate Similarity	NPD7240	Approved
0.7574	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7568	Intermediate Similarity	NPD8434	Phase 2
0.7556	Intermediate Similarity	NPD2163	Approved
0.7545	Intermediate Similarity	NPD4628	Phase 3
0.7529	Intermediate Similarity	NPD1465	Phase 2
0.7529	Intermediate Similarity	NPD1512	Approved
0.7514	Intermediate Similarity	NPD7411	Suspended
0.75	Intermediate Similarity	NPD6190	Approved
0.747	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7457	Intermediate Similarity	NPD6599	Discontinued
0.7442	Intermediate Similarity	NPD1653	Approved
0.7412	Intermediate Similarity	NPD1511	Approved
0.7409	Intermediate Similarity	NPD6780	Approved
0.7409	Intermediate Similarity	NPD6778	Approved
0.7409	Intermediate Similarity	NPD6776	Approved
0.7409	Intermediate Similarity	NPD6781	Approved
0.7409	Intermediate Similarity	NPD6777	Approved
0.7409	Intermediate Similarity	NPD6782	Approved
0.7409	Intermediate Similarity	NPD6779	Approved
0.7407	Intermediate Similarity	NPD6798	Discontinued
0.7386	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7385	Intermediate Similarity	NPD7435	Discontinued
0.7384	Intermediate Similarity	NPD920	Approved
0.7384	Intermediate Similarity	NPD5403	Approved
0.7381	Intermediate Similarity	NPD6674	Discontinued
0.7374	Intermediate Similarity	NPD6959	Discontinued
0.7368	Intermediate Similarity	NPD5401	Approved
0.7365	Intermediate Similarity	NPD7266	Discontinued
0.7365	Intermediate Similarity	NPD2344	Approved
0.7321	Intermediate Similarity	NPD1549	Phase 2
0.7305	Intermediate Similarity	NPD2796	Approved
0.7303	Intermediate Similarity	NPD3749	Approved
0.7299	Intermediate Similarity	NPD7458	Discontinued
0.7273	Intermediate Similarity	NPD6355	Discontinued
0.7273	Intermediate Similarity	NPD1933	Approved
0.7267	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7262	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7262	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7259	Intermediate Similarity	NPD7870	Phase 2
0.7259	Intermediate Similarity	NPD7871	Phase 2
0.7256	Intermediate Similarity	NPD6233	Phase 2
0.7253	Intermediate Similarity	NPD4575	Clinical (unspecified phase)
0.7253	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7246	Intermediate Similarity	NPD5619	Clinical (unspecified phase)
0.7208	Intermediate Similarity	NPD7697	Approved
0.7208	Intermediate Similarity	NPD7698	Approved
0.7208	Intermediate Similarity	NPD7696	Phase 3
0.72	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD3226	Approved
0.72	Intermediate Similarity	NPD8151	Discontinued
0.7193	Intermediate Similarity	NPD2309	Approved
0.7182	Intermediate Similarity	NPD8127	Discontinued
0.7176	Intermediate Similarity	NPD1243	Approved
0.7164	Intermediate Similarity	NPD7874	Approved
0.7164	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD2346	Discontinued
0.7151	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.715	Intermediate Similarity	NPD7701	Phase 2
0.715	Intermediate Similarity	NPD6535	Approved
0.715	Intermediate Similarity	NPD6534	Approved
0.7143	Intermediate Similarity	NPD2799	Discontinued
0.7129	Intermediate Similarity	NPD7783	Phase 2
0.7129	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7121	Intermediate Similarity	NPD7680	Approved
0.7118	Intermediate Similarity	NPD2424	Discontinued
0.7112	Intermediate Similarity	NPD6764	Approved
0.7112	Intermediate Similarity	NPD6765	Approved
0.7108	Intermediate Similarity	NPD1613	Approved
0.7108	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD2935	Discontinued
0.7091	Intermediate Similarity	NPD2313	Discontinued
0.7081	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7072	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7071	Intermediate Similarity	NPD3057	Approved
0.7066	Intermediate Similarity	NPD447	Suspended
0.7062	Intermediate Similarity	NPD7028	Phase 2
0.7059	Intermediate Similarity	NPD1471	Phase 3
0.7056	Intermediate Similarity	NPD7768	Phase 2
0.7052	Intermediate Similarity	NPD5058	Phase 3
0.705	Intermediate Similarity	NPD7999	Approved
0.7049	Intermediate Similarity	NPD7229	Phase 3
0.7044	Intermediate Similarity	NPD7801	Approved
0.7041	Intermediate Similarity	NPD7699	Phase 2
0.7041	Intermediate Similarity	NPD1510	Phase 2
0.7041	Intermediate Similarity	NPD7700	Phase 2
0.7029	Intermediate Similarity	NPD5049	Phase 3
0.7022	Intermediate Similarity	NPD6386	Approved
0.7022	Intermediate Similarity	NPD6385	Approved
0.7016	Intermediate Similarity	NPD8150	Discontinued
0.7015	Intermediate Similarity	NPD7584	Approved
0.7012	Intermediate Similarity	NPD9494	Approved
0.7006	Intermediate Similarity	NPD4060	Phase 1
0.7005	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD8320	Phase 1
0.7	Intermediate Similarity	NPD8319	Approved
0.6994	Remote Similarity	NPD3887	Approved
0.6994	Remote Similarity	NPD2354	Approved
0.699	Remote Similarity	NPD8090	Clinical (unspecified phase)
0.6988	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6985	Remote Similarity	NPD6823	Phase 2
0.6985	Remote Similarity	NPD3533	Approved
0.6985	Remote Similarity	NPD2972	Approved
0.6971	Remote Similarity	NPD2532	Approved
0.6971	Remote Similarity	NPD2534	Approved
0.6971	Remote Similarity	NPD2533	Approved
0.6964	Remote Similarity	NPD230	Phase 1
0.6963	Remote Similarity	NPD6785	Approved
0.6963	Remote Similarity	NPD6784	Approved
0.6957	Remote Similarity	NPD1091	Approved
0.6954	Remote Similarity	NPD4420	Approved
0.6944	Remote Similarity	NPD5761	Phase 2
0.6944	Remote Similarity	NPD5760	Phase 2
0.6942	Remote Similarity	NPD7930	Approved
0.6941	Remote Similarity	NPD7033	Discontinued
0.6936	Remote Similarity	NPD3750	Approved
0.6932	Remote Similarity	NPD6273	Approved
0.6931	Remote Similarity	NPD7038	Approved
0.6931	Remote Similarity	NPD7039	Approved
0.6931	Remote Similarity	NPD7583	Approved
0.6928	Remote Similarity	NPD3027	Phase 3
0.6905	Remote Similarity	NPD1240	Approved
0.6905	Remote Similarity	NPD8155	Clinical (unspecified phase)
0.6904	Remote Similarity	NPD2974	Approved
0.6904	Remote Similarity	NPD2975	Approved
0.6904	Remote Similarity	NPD2973	Approved
0.6898	Remote Similarity	NPD7799	Discontinued
0.6897	Remote Similarity	NPD7585	Approved
0.689	Remote Similarity	NPD1049	Clinical (unspecified phase)
0.6884	Remote Similarity	NPD4107	Approved
0.6884	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.6882	Remote Similarity	NPD7097	Phase 1
0.6879	Remote Similarity	NPD2800	Approved
0.6879	Remote Similarity	NPD5698	Clinical (unspecified phase)
0.6878	Remote Similarity	NPD3823	Discontinued
0.6871	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6865	Remote Similarity	NPD6808	Phase 2
0.686	Remote Similarity	NPD5763	Approved
0.686	Remote Similarity	NPD6004	Phase 3
0.686	Remote Similarity	NPD6005	Phase 3
0.686	Remote Similarity	NPD6002	Phase 3
0.686	Remote Similarity	NPD6003	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