NPASS Compound

Structure

NPC106625 OpenBabel07101719512D 32 34 0 0 1 0 0 0 0 0999 V2000 -1.7321 4.0000 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 6.0622 2.5000 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 6.0622 4.5000 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 3.0000 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 0.0000 3.0000 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 5.1962 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 4.0000 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 2.5981 2.5000 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 2.5000 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 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 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 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 7.7942 4.5000 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 2.5981 4.5000 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 -0.8660 4.5000 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 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 5 1 0 0 0 0 2 11 2 0 0 0 0 3 6 2 0 0 0 0 3 11 1 0 0 0 0 4 7 1 0 0 0 0 4 11 1 0 0 0 0 5 12 2 0 0 0 0 6 12 1 0 0 0 0 7 14 1 0 0 0 0 8 13 2 0 0 0 0 8 15 1 0 0 0 0 9 13 1 0 0 0 0 9 16 2 0 0 0 0 10 23 1 0 0 0 0 12 24 1 0 0 0 0 13 30 1 0 0 0 0 14 18 1 0 0 0 0 14 25 2 0 0 0 0 15 18 2 0 0 0 0 15 26 1 0 0 0 0 16 18 1 0 0 0 0 16 31 1 0 0 0 0 17 10 1 6 0 0 0 17 19 1 0 0 0 0 17 32 1 0 0 0 0 19 20 1 0 0 0 0 19 27 1 1 0 0 0 20 21 1 0 0 0 0 20 28 1 6 0 0 0 21 22 1 0 0 0 0 21 29 1 1 0 0 0 22 31 1 6 0 0 0 22 32 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	450.15
Volume:	432.846
LogP:	1.074
LogD:	1.175
LogS:	-3.541
# Rotatable Bonds:	8
TPSA:	166.14
# H-Bond Aceptor:	10
# H-Bond Donor:	6
# Rings:	3
# Heavy Atoms:	10

MedChem Properties

QED Drug-Likeness Score:	0.304
Synthetic Accessibility Score:	3.726
Fsp3:	0.409
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:	-6.316
MDCK Permeability:	8.874130799085833e-06
Pgp-inhibitor:	0.012
Pgp-substrate:	0.087
Human Intestinal Absorption (HIA):	0.837
20% Bioavailability (F20%):	0.012
30% Bioavailability (F30%):	0.995

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.112
Plasma Protein Binding (PPB):	85.86642456054688%
Volume Distribution (VD):	0.741
Pgp-substrate:	4.678420543670654%

ADMET: Metabolism

CYP1A2-inhibitor:	0.339
CYP1A2-substrate:	0.076
CYP2C19-inhibitor:	0.068
CYP2C19-substrate:	0.106
CYP2C9-inhibitor:	0.051
CYP2C9-substrate:	0.789
CYP2D6-inhibitor:	0.646
CYP2D6-substrate:	0.578
CYP3A4-inhibitor:	0.062
CYP3A4-substrate:	0.076

ADMET: Excretion

Clearance (CL):	8.965
Half-life (T1/2):	0.785

ADMET: Toxicity

hERG Blockers:	0.211
Human Hepatotoxicity (H-HT):	0.06
Drug-inuced Liver Injury (DILI):	0.605
AMES Toxicity:	0.333
Rat Oral Acute Toxicity:	0.068
Maximum Recommended Daily Dose:	0.009
Skin Sensitization:	0.818
Carcinogencity:	0.19
Eye Corrosion:	0.003
Eye Irritation:	0.101
Respiratory Toxicity:	0.027

Download Data

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

Natural Product: NPC106625

Natural Product ID:	NPC106625
*Common Name:**	Asebotin
IUPAC Name:	1-[2-hydroxy-4-methoxy-6-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]-3-(4-hydroxyphenyl)propan-1-one
Synonyms:	Asebotin
Standard InCHIKey:	PQCIBORQLVRFMR-MIUGBVLSSA-N
Standard InCHI:	InChI=1S/C22H26O10/c1-30-13-8-15(26)18(14(25)7-4-11-2-5-12(24)6-3-11)16(9-13)31-22-21(29)20(28)19(27)17(10-23)32-22/h2-3,5-6,8-9,17,19-24,26-29H,4,7,10H2,1H3/t17-,19-,20+,21-,22-/m1/s1
SMILES:	OC[C@H]1O[C@@H](Oc2cc(OC)cc(c2C(=O)CCc2ccc(cc2)O)O)[C@@H]([C@H]([C@@H]1O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL490513
PubChem CID:	11190157
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
NPO13961	Pieris japonica	Species	Ericaceae	Eukaryota	leaves	n.a.	n.a.	PMID[15787442]
NPO13961	Pieris japonica	Species	Ericaceae	Eukaryota	n.a.	leaf	n.a.	PMID[15787442]
NPO13961	Pieris japonica	Species	Ericaceae	Eukaryota	Leaves	n.a.	n.a.	PMID[31809052]
NPO19198	Kalmia latifolia	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[521818]
NPO13961	Pieris japonica	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO19198	Kalmia latifolia	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO13961	Pieris japonica	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19198	Kalmia latifolia	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19198	Kalmia latifolia	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[Title]
NPO19198	Kalmia latifolia	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13961	Pieris japonica	Species	Ericaceae	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	8

Activity Type	# Activity
NON-MOLECULAR	8

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	100.0	%	PMID[539050]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	35.16	10'-3cpm	PMID[539051]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	40.73	10'-3cpm	PMID[539051]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	47.42	10'-3cpm	PMID[539051]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	79.57	10'-3cpm	PMID[539051]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	87.19	10'-3cpm	PMID[539051]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	89.78	10'-3cpm	PMID[539051]

☑ 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 NPC106625 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	367
0.1-0.2	1426
0.2-0.3	3383
0.3-0.4	8347
0.4-0.5	10076
0.5-0.6	4262
0.6-0.7	5225
0.7-0.8	5749
0.8-0.85	2509
0.85-0.9	1126
0.9-0.95	191
0.95-1	36

Similarity Score	Similarity Level	Natural Product ID
0.9932	High Similarity	NPC121001
0.9932	High Similarity	NPC259182
0.9932	High Similarity	NPC99233
0.9865	High Similarity	NPC127406
0.9865	High Similarity	NPC206378
0.9799	High Similarity	NPC6985
0.9799	High Similarity	NPC23817
0.9799	High Similarity	NPC43638
0.9797	High Similarity	NPC26195
0.9797	High Similarity	NPC169248
0.9797	High Similarity	NPC72649
0.9797	High Similarity	NPC95090
0.9797	High Similarity	NPC27408
0.9797	High Similarity	NPC39351
0.9797	High Similarity	NPC97052
0.9796	High Similarity	NPC259767
0.9796	High Similarity	NPC88484
0.9733	High Similarity	NPC73511
0.9732	High Similarity	NPC170475
0.973	High Similarity	NPC210003
0.973	High Similarity	NPC143851
0.973	High Similarity	NPC83283
0.973	High Similarity	NPC39360
0.973	High Similarity	NPC29763
0.9669	High Similarity	NPC142860
0.9669	High Similarity	NPC246469
0.9669	High Similarity	NPC271270
0.9669	High Similarity	NPC97285
0.9669	High Similarity	NPC153342
0.9667	High Similarity	NPC258035
0.9667	High Similarity	NPC65003
0.9667	High Similarity	NPC473512
0.9667	High Similarity	NPC156457
0.9667	High Similarity	NPC44931
0.9667	High Similarity	NPC108831
0.9667	High Similarity	NPC129827
0.9667	High Similarity	NPC313163
0.9667	High Similarity	NPC197896
0.9667	High Similarity	NPC60966
0.9667	High Similarity	NPC182634
0.9667	High Similarity	NPC161749
0.966	High Similarity	NPC214454
0.966	High Similarity	NPC106025
0.966	High Similarity	NPC477240
0.966	High Similarity	NPC191154
0.9658	High Similarity	NPC199335
0.9605	High Similarity	NPC303913
0.9603	High Similarity	NPC320283
0.9603	High Similarity	NPC472459
0.9603	High Similarity	NPC308265
0.9603	High Similarity	NPC22062
0.9603	High Similarity	NPC41121
0.9603	High Similarity	NPC138811
0.9603	High Similarity	NPC473634
0.9603	High Similarity	NPC111929
0.96	High Similarity	NPC149368
0.96	High Similarity	NPC45165
0.96	High Similarity	NPC307938
0.96	High Similarity	NPC323593
0.96	High Similarity	NPC265480
0.96	High Similarity	NPC203500
0.9597	High Similarity	NPC211158
0.9597	High Similarity	NPC268950
0.9597	High Similarity	NPC108706
0.9597	High Similarity	NPC78021
0.9597	High Similarity	NPC87304
0.9595	High Similarity	NPC134819
0.9595	High Similarity	NPC190217
0.9589	High Similarity	NPC23084
0.9542	High Similarity	NPC44947
0.9542	High Similarity	NPC190450
0.9542	High Similarity	NPC131745
0.9542	High Similarity	NPC300537
0.9542	High Similarity	NPC127782
0.9542	High Similarity	NPC259834
0.9539	High Similarity	NPC472320
0.9539	High Similarity	NPC473623
0.9539	High Similarity	NPC187379
0.9539	High Similarity	NPC200708
0.9539	High Similarity	NPC271479
0.9536	High Similarity	NPC78263
0.9536	High Similarity	NPC133671
0.9536	High Similarity	NPC54802
0.9536	High Similarity	NPC135391
0.9536	High Similarity	NPC77672
0.9536	High Similarity	NPC197304
0.9536	High Similarity	NPC122809
0.9533	High Similarity	NPC470603
0.9533	High Similarity	NPC470605
0.9533	High Similarity	NPC470604
0.9527	High Similarity	NPC213723
0.9481	High Similarity	NPC124155
0.9481	High Similarity	NPC183672
0.9481	High Similarity	NPC278419
0.9481	High Similarity	NPC257566
0.9481	High Similarity	NPC179198
0.9481	High Similarity	NPC66087
0.9477	High Similarity	NPC276377
0.9477	High Similarity	NPC473438
0.9477	High Similarity	NPC215710
0.9477	High Similarity	NPC265885
0.9477	High Similarity	NPC159579
0.9477	High Similarity	NPC47923
0.9477	High Similarity	NPC224530
0.9477	High Similarity	NPC249281
0.9477	High Similarity	NPC181465
0.9477	High Similarity	NPC246943
0.9477	High Similarity	NPC139320
0.9477	High Similarity	NPC173582
0.9477	High Similarity	NPC476215
0.9477	High Similarity	NPC101636
0.9477	High Similarity	NPC116458
0.9477	High Similarity	NPC259957
0.9477	High Similarity	NPC253788
0.9477	High Similarity	NPC163242
0.9477	High Similarity	NPC129217
0.9477	High Similarity	NPC216496
0.9477	High Similarity	NPC85707
0.9477	High Similarity	NPC48093
0.9474	High Similarity	NPC43761
0.947	High Similarity	NPC473657
0.947	High Similarity	NPC295613
0.947	High Similarity	NPC261866
0.9456	High Similarity	NPC218685
0.9416	High Similarity	NPC240306
0.9416	High Similarity	NPC150164
0.9416	High Similarity	NPC472876
0.9416	High Similarity	NPC475382
0.9416	High Similarity	NPC298171
0.9416	High Similarity	NPC27942
0.9412	High Similarity	NPC471079
0.9412	High Similarity	NPC136761
0.9412	High Similarity	NPC470405
0.9412	High Similarity	NPC304741
0.9408	High Similarity	NPC288084
0.9408	High Similarity	NPC470606
0.9396	High Similarity	NPC38775
0.9359	High Similarity	NPC5778
0.9359	High Similarity	NPC236934
0.9359	High Similarity	NPC70441
0.9355	High Similarity	NPC243930
0.9355	High Similarity	NPC121703
0.9355	High Similarity	NPC473644
0.9355	High Similarity	NPC29830
0.9355	High Similarity	NPC311850
0.9355	High Similarity	NPC88023
0.9355	High Similarity	NPC19709
0.9355	High Similarity	NPC309025
0.9351	High Similarity	NPC477628
0.9351	High Similarity	NPC270675
0.9351	High Similarity	NPC170052
0.9351	High Similarity	NPC297987
0.9351	High Similarity	NPC64305
0.9351	High Similarity	NPC282169
0.9351	High Similarity	NPC210961
0.9351	High Similarity	NPC472994
0.9351	High Similarity	NPC477629
0.9351	High Similarity	NPC135846
0.9351	High Similarity	NPC195685
0.9351	High Similarity	NPC470125
0.9346	High Similarity	NPC470607
0.9346	High Similarity	NPC104677
0.9333	High Similarity	NPC23253
0.9324	High Similarity	NPC44721
0.9324	High Similarity	NPC176869
0.9324	High Similarity	NPC40086
0.9324	High Similarity	NPC122828
0.9324	High Similarity	NPC3779
0.9324	High Similarity	NPC476182
0.9324	High Similarity	NPC211466
0.9324	High Similarity	NPC302989
0.9299	High Similarity	NPC229729
0.9295	High Similarity	NPC22832
0.9295	High Similarity	NPC287889
0.9295	High Similarity	NPC135358
0.9295	High Similarity	NPC72016
0.9295	High Similarity	NPC311830
0.9295	High Similarity	NPC139060
0.9295	High Similarity	NPC165720
0.929	High Similarity	NPC93215
0.929	High Similarity	NPC473043
0.929	High Similarity	NPC77660
0.929	High Similarity	NPC189142
0.9272	High Similarity	NPC10807
0.9272	High Similarity	NPC150123
0.9272	High Similarity	NPC244583
0.9272	High Similarity	NPC161881
0.9272	High Similarity	NPC56232
0.9241	High Similarity	NPC472381
0.9241	High Similarity	NPC43587
0.9241	High Similarity	NPC293629
0.9241	High Similarity	NPC270578
0.9241	High Similarity	NPC5319
0.9241	High Similarity	NPC52382
0.9241	High Similarity	NPC229687
0.9241	High Similarity	NPC472383
0.9236	High Similarity	NPC12013
0.9236	High Similarity	NPC210073
0.9236	High Similarity	NPC262222
0.9236	High Similarity	NPC115674

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 NPC106625 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	313
0.1-0.2	841
0.2-0.3	1673
0.3-0.4	2637
0.4-0.5	1961
0.5-0.6	1125
0.6-0.7	391
0.7-0.8	161
0.8-0.85	29
0.85-0.9	17
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9667	High Similarity	NPD4381	Clinical (unspecified phase)
0.9241	High Similarity	NPD7804	Clinical (unspecified phase)
0.9182	High Similarity	NPD7074	Phase 3
0.9119	High Similarity	NPD7054	Approved
0.9062	High Similarity	NPD7472	Approved
0.9057	High Similarity	NPD3818	Discontinued
0.9013	High Similarity	NPD4380	Phase 2
0.9006	High Similarity	NPD6797	Phase 2
0.8973	High Similarity	NPD1552	Clinical (unspecified phase)
0.8973	High Similarity	NPD1550	Clinical (unspecified phase)
0.8951	High Similarity	NPD7251	Discontinued
0.8912	High Similarity	NPD1549	Phase 2
0.891	High Similarity	NPD7075	Discontinued
0.8896	High Similarity	NPD7808	Phase 3
0.8896	High Similarity	NPD1934	Approved
0.8839	High Similarity	NPD2393	Clinical (unspecified phase)
0.8834	High Similarity	NPD6559	Discontinued
0.878	High Similarity	NPD4338	Clinical (unspecified phase)
0.8774	High Similarity	NPD6801	Discontinued
0.8718	High Similarity	NPD7096	Clinical (unspecified phase)
0.8696	High Similarity	NPD6168	Clinical (unspecified phase)
0.8696	High Similarity	NPD6167	Clinical (unspecified phase)
0.8696	High Similarity	NPD6166	Phase 2
0.8684	High Similarity	NPD4378	Clinical (unspecified phase)
0.8618	High Similarity	NPD6799	Approved
0.859	High Similarity	NPD7411	Suspended
0.8544	High Similarity	NPD8443	Clinical (unspecified phase)
0.8523	High Similarity	NPD2796	Approved
0.8481	Intermediate Similarity	NPD2801	Approved
0.8456	Intermediate Similarity	NPD1510	Phase 2
0.8452	Intermediate Similarity	NPD5403	Approved
0.8442	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8435	Intermediate Similarity	NPD1240	Approved
0.8428	Intermediate Similarity	NPD3817	Phase 2
0.8408	Intermediate Similarity	NPD6599	Discontinued
0.8377	Intermediate Similarity	NPD1511	Approved
0.8375	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8365	Intermediate Similarity	NPD7819	Suspended
0.8323	Intermediate Similarity	NPD5401	Approved
0.8322	Intermediate Similarity	NPD1607	Approved
0.8269	Intermediate Similarity	NPD1512	Approved
0.8261	Intermediate Similarity	NPD3882	Suspended
0.8199	Intermediate Similarity	NPD5402	Approved
0.8171	Intermediate Similarity	NPD6959	Discontinued
0.8133	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8065	Intermediate Similarity	NPD4628	Phase 3
0.8065	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.8057	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.8054	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD5494	Approved
0.8	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7978	Intermediate Similarity	NPD7584	Approved
0.7965	Intermediate Similarity	NPD8313	Approved
0.7965	Intermediate Similarity	NPD8312	Approved
0.7949	Intermediate Similarity	NPD3750	Approved
0.7927	Intermediate Similarity	NPD7768	Phase 2
0.7922	Intermediate Similarity	NPD1551	Phase 2
0.7914	Intermediate Similarity	NPD8455	Phase 2
0.7904	Intermediate Similarity	NPD6232	Discontinued
0.7882	Intermediate Similarity	NPD5844	Phase 1
0.7879	Intermediate Similarity	NPD3749	Approved
0.7875	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.787	Intermediate Similarity	NPD7473	Discontinued
0.7844	Intermediate Similarity	NPD7199	Phase 2
0.7826	Intermediate Similarity	NPD1653	Approved
0.7824	Intermediate Similarity	NPD3751	Discontinued
0.7821	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7808	Intermediate Similarity	NPD1091	Approved
0.7798	Intermediate Similarity	NPD3787	Discontinued
0.7778	Intermediate Similarity	NPD1933	Approved
0.7771	Intermediate Similarity	NPD2800	Approved
0.7747	Intermediate Similarity	NPD6780	Approved
0.7747	Intermediate Similarity	NPD6782	Approved
0.7747	Intermediate Similarity	NPD6776	Approved
0.7747	Intermediate Similarity	NPD6778	Approved
0.7747	Intermediate Similarity	NPD6781	Approved
0.7747	Intermediate Similarity	NPD6777	Approved
0.7747	Intermediate Similarity	NPD6779	Approved
0.7742	Intermediate Similarity	NPD7033	Discontinued
0.7727	Intermediate Similarity	NPD6651	Approved
0.7712	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7712	Intermediate Similarity	NPD1613	Approved
0.7697	Intermediate Similarity	NPD1465	Phase 2
0.7692	Intermediate Similarity	NPD2935	Discontinued
0.7688	Intermediate Similarity	NPD5953	Discontinued
0.7687	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7682	Intermediate Similarity	NPD6832	Phase 2
0.768	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7674	Intermediate Similarity	NPD7286	Phase 2
0.7654	Intermediate Similarity	NPD920	Approved
0.7647	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.764	Intermediate Similarity	NPD2533	Approved
0.764	Intermediate Similarity	NPD2532	Approved
0.764	Intermediate Similarity	NPD2534	Approved
0.7636	Intermediate Similarity	NPD37	Approved
0.7628	Intermediate Similarity	NPD3748	Approved
0.7622	Intermediate Similarity	NPD7435	Discontinued
0.7619	Intermediate Similarity	NPD6234	Discontinued
0.7616	Intermediate Similarity	NPD7228	Approved
0.7606	Intermediate Similarity	NPD8151	Discontinued
0.7605	Intermediate Similarity	NPD4967	Phase 2
0.7605	Intermediate Similarity	NPD4965	Approved
0.7605	Intermediate Similarity	NPD4966	Approved
0.76	Intermediate Similarity	NPD1203	Approved
0.76	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7582	Intermediate Similarity	NPD6798	Discontinued
0.7578	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7566	Intermediate Similarity	NPD4908	Phase 1
0.7561	Intermediate Similarity	NPD7458	Discontinued
0.7553	Intermediate Similarity	NPD7585	Approved
0.755	Intermediate Similarity	NPD2798	Approved
0.7547	Intermediate Similarity	NPD1243	Approved
0.7547	Intermediate Similarity	NPD1652	Phase 2
0.7543	Intermediate Similarity	NPD7685	Pre-registration
0.7532	Intermediate Similarity	NPD2344	Approved
0.7531	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7527	Intermediate Similarity	NPD7696	Phase 3
0.7527	Intermediate Similarity	NPD7697	Approved
0.7527	Intermediate Similarity	NPD7698	Approved
0.7526	Intermediate Similarity	NPD7783	Phase 2
0.7526	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD2799	Discontinued
0.7516	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7583	Approved
0.7487	Intermediate Similarity	NPD7870	Phase 2
0.7487	Intermediate Similarity	NPD7871	Phase 2
0.7484	Intermediate Similarity	NPD943	Approved
0.7473	Intermediate Similarity	NPD6535	Approved
0.7473	Intermediate Similarity	NPD6534	Approved
0.7473	Intermediate Similarity	NPD4363	Phase 3
0.7473	Intermediate Similarity	NPD4360	Phase 2
0.7473	Intermediate Similarity	NPD6823	Phase 2
0.747	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD6099	Approved
0.7468	Intermediate Similarity	NPD3268	Approved
0.7468	Intermediate Similarity	NPD2313	Discontinued
0.7468	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD6100	Approved
0.746	Intermediate Similarity	NPD7701	Phase 2
0.7455	Intermediate Similarity	NPD3226	Approved
0.7451	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.745	Intermediate Similarity	NPD1610	Phase 2
0.7444	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7442	Intermediate Similarity	NPD3926	Phase 2
0.7436	Intermediate Similarity	NPD5124	Phase 1
0.7436	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7423	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7421	Intermediate Similarity	NPD7266	Discontinued
0.7419	Intermediate Similarity	NPD6233	Phase 2
0.7415	Intermediate Similarity	NPD1548	Phase 1
0.7412	Intermediate Similarity	NPD919	Approved
0.7403	Intermediate Similarity	NPD3027	Phase 3
0.74	Intermediate Similarity	NPD9717	Approved
0.7386	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7382	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7382	Intermediate Similarity	NPD7874	Approved
0.7374	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD2797	Approved
0.7351	Intermediate Similarity	NPD7699	Phase 2
0.7351	Intermediate Similarity	NPD7700	Phase 2
0.7346	Intermediate Similarity	NPD2309	Approved
0.7344	Intermediate Similarity	NPD7801	Approved
0.7333	Intermediate Similarity	NPD422	Phase 1
0.7333	Intermediate Similarity	NPD8434	Phase 2
0.7326	Intermediate Similarity	NPD1247	Approved
0.7325	Intermediate Similarity	NPD230	Phase 1
0.7325	Intermediate Similarity	NPD6355	Discontinued
0.7317	Intermediate Similarity	NPD4662	Approved
0.7317	Intermediate Similarity	NPD4661	Approved
0.7312	Intermediate Similarity	NPD2346	Discontinued
0.7299	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7284	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD2424	Discontinued
0.7256	Intermediate Similarity	NPD7390	Discontinued
0.7247	Intermediate Similarity	NPD7240	Approved
0.7239	Intermediate Similarity	NPD6190	Approved
0.7233	Intermediate Similarity	NPD7097	Phase 1
0.7228	Intermediate Similarity	NPD6212	Phase 3
0.7228	Intermediate Similarity	NPD6213	Phase 3
0.7228	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD2654	Approved
0.7215	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7215	Intermediate Similarity	NPD447	Suspended
0.7211	Intermediate Similarity	NPD8319	Approved
0.7211	Intermediate Similarity	NPD8320	Phase 1
0.719	Intermediate Similarity	NPD3225	Approved
0.7188	Intermediate Similarity	NPD4308	Phase 3
0.7188	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7184	Intermediate Similarity	NPD5711	Approved
0.7184	Intermediate Similarity	NPD5710	Approved
0.7181	Intermediate Similarity	NPD9545	Approved
0.7181	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD4361	Phase 2
0.7151	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD3266	Approved
0.7143	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD3267	Approved
0.7143	Intermediate Similarity	NPD7930	Approved
0.7143	Intermediate Similarity	NPD8150	Discontinued

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