NPASS Compound

Structure

NPC23084 OpenBabel07101719142D 24 25 0 0 1 0 0 0 0 0999 V2000 -5.1962 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 0.0000 0.0000 C 0 0 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 1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -2.0000 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 -4.3301 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 2 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 -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 2.5981 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 0.0000 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 -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 -3.4641 -3.0000 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 6 1 0 0 0 0 2 22 1 0 0 0 0 3 7 2 0 0 0 0 3 8 1 0 0 0 0 4 7 1 0 0 0 0 4 9 2 0 0 0 0 5 16 1 0 0 0 0 6 11 1 0 0 0 0 6 17 2 0 0 0 0 7 23 1 0 0 0 0 8 11 2 0 0 0 0 8 18 1 0 0 0 0 9 11 1 0 0 0 0 9 22 1 0 0 0 0 10 5 1 6 0 0 0 10 12 1 0 0 0 0 10 24 1 0 0 0 0 12 13 1 0 0 0 0 12 19 1 1 0 0 0 13 14 1 0 0 0 0 13 20 1 6 0 0 0 14 15 1 0 0 0 0 14 21 1 1 0 0 0 15 23 1 6 0 0 0 15 24 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	344.11
Volume:	319.45
LogP:	-0.294
LogD:	-0.25
LogS:	-1.357
# Rotatable Bonds:	5
TPSA:	145.91
# H-Bond Aceptor:	9
# H-Bond Donor:	5
# Rings:	2
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.415
Synthetic Accessibility Score:	3.655
Fsp3:	0.533
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.192
MDCK Permeability:	4.0353192162001505e-05
Pgp-inhibitor:	0.008
Pgp-substrate:	0.276
Human Intestinal Absorption (HIA):	0.86
20% Bioavailability (F20%):	0.006
30% Bioavailability (F30%):	0.946

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.398
Plasma Protein Binding (PPB):	60.16794967651367%
Volume Distribution (VD):	0.789
Pgp-substrate:	28.714508056640625%

ADMET: Metabolism

CYP1A2-inhibitor:	0.129
CYP1A2-substrate:	0.11
CYP2C19-inhibitor:	0.018
CYP2C19-substrate:	0.472
CYP2C9-inhibitor:	0.004
CYP2C9-substrate:	0.271
CYP2D6-inhibitor:	0.03
CYP2D6-substrate:	0.22
CYP3A4-inhibitor:	0.011
CYP3A4-substrate:	0.052

ADMET: Excretion

Clearance (CL):	3.597
Half-life (T1/2):	0.778

ADMET: Toxicity

hERG Blockers:	0.127
Human Hepatotoxicity (H-HT):	0.041
Drug-inuced Liver Injury (DILI):	0.669
AMES Toxicity:	0.332
Rat Oral Acute Toxicity:	0.03
Maximum Recommended Daily Dose:	0.005
Skin Sensitization:	0.118
Carcinogencity:	0.087
Eye Corrosion:	0.004
Eye Irritation:	0.294
Respiratory Toxicity:	0.095

Download Data

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

Natural Product: NPC23084

Natural Product ID:	NPC23084
*Common Name:**	4-O-Beta-D-Glucopyranosyl-2-Hydroxy-6-Methoxyacetophenone
IUPAC Name:	1-[2-hydroxy-6-methoxy-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]ethanone
Synonyms:
Standard InCHIKey:	DNMNFEFVHVMPES-TVKJYDDYSA-N
Standard InCHI:	InChI=1S/C15H20O9/c1-6(17)11-8(18)3-7(4-9(11)22-2)23-15-14(21)13(20)12(19)10(5-16)24-15/h3-4,10,12-16,18-21H,5H2,1-2H3/t10-,12-,13+,14-,15-/m1/s1
SMILES:	OC[C@H]1O[C@@H](Oc2cc(O)c(c(c2)OC)C(=O)C)[C@@H]([C@H]([C@@H]1O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3402766
PubChem CID:	15929152
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
NPO11100	Artemisia capillaris	Species	Asteraceae	Eukaryota	n.a.	whole plant	n.a.	PMID[21428416]
NPO11100	Artemisia capillaris	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22870812]
NPO11100	Artemisia capillaris	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23435948]
NPO11100	Artemisia capillaris	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25737008]
NPO11100	Artemisia capillaris	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11100	Artemisia capillaris	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11100	Artemisia capillaris	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO11100	Artemisia capillaris	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO11100	Artemisia capillaris	Species	Asteraceae	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	3
Others	2

Activity Type	# Activity
Organism	3
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT963	Organism	Hepatitis B virus	Hepatitis B virus	IC50	>	2365500.0	nM	PMID[473483]
NPT27	Others	Unspecified		CC50	>	2365500.0	nM	PMID[473483]
NPT963	Organism	Hepatitis B virus	Hepatitis B virus	IC50	=	92000.0	nM	PMID[473483]
NPT2	Others	Unspecified		Selectivity Index	>	25.7	n.a.	PMID[473483]

☑ 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 NPC23084 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	356
0.1-0.2	1450
0.2-0.3	3771
0.3-0.4	8829
0.4-0.5	9714
0.5-0.6	4104
0.6-0.7	5544
0.7-0.8	6107
0.8-0.85	2177
0.85-0.9	556
0.9-0.95	72
0.95-1	17

Similarity Score	Similarity Level	Natural Product ID
0.9929	High Similarity	NPC199335
0.979	High Similarity	NPC477240
0.979	High Similarity	NPC106025
0.979	High Similarity	NPC214454
0.979	High Similarity	NPC191154
0.9722	High Similarity	NPC190217
0.9722	High Similarity	NPC134819
0.9718	High Similarity	NPC218685
0.9589	High Similarity	NPC268950
0.9589	High Similarity	NPC108706
0.9589	High Similarity	NPC78021
0.9589	High Similarity	NPC87304
0.9589	High Similarity	NPC211158
0.9589	High Similarity	NPC106625
0.9524	High Similarity	NPC470603
0.9524	High Similarity	NPC470604
0.9524	High Similarity	NPC95090
0.9524	High Similarity	NPC27408
0.9524	High Similarity	NPC99233
0.9524	High Similarity	NPC470605
0.9521	High Similarity	NPC259182
0.9521	High Similarity	NPC259767
0.9521	High Similarity	NPC121001
0.9521	High Similarity	NPC88484
0.9517	High Similarity	NPC213723
0.9459	High Similarity	NPC127406
0.9459	High Similarity	NPC206378
0.9456	High Similarity	NPC39360
0.9456	High Similarity	NPC143851
0.9456	High Similarity	NPC29763
0.9456	High Similarity	NPC210003
0.9456	High Similarity	NPC83283
0.9452	High Similarity	NPC23253
0.9396	High Similarity	NPC108831
0.9396	High Similarity	NPC44931
0.9396	High Similarity	NPC473512
0.9396	High Similarity	NPC60966
0.9396	High Similarity	NPC129827
0.9396	High Similarity	NPC23817
0.9396	High Similarity	NPC6985
0.9396	High Similarity	NPC43638
0.9396	High Similarity	NPC182634
0.9396	High Similarity	NPC470606
0.9396	High Similarity	NPC65003
0.9392	High Similarity	NPC97052
0.9392	High Similarity	NPC26195
0.9392	High Similarity	NPC72649
0.9392	High Similarity	NPC169248
0.9392	High Similarity	NPC39351
0.9384	High Similarity	NPC38775
0.9333	High Similarity	NPC22062
0.9333	High Similarity	NPC73511
0.9333	High Similarity	NPC111929
0.9333	High Similarity	NPC470607
0.9333	High Similarity	NPC320283
0.9333	High Similarity	NPC473634
0.9333	High Similarity	NPC472459
0.9333	High Similarity	NPC138811
0.9333	High Similarity	NPC41121
0.9329	High Similarity	NPC203500
0.9329	High Similarity	NPC323593
0.9329	High Similarity	NPC307938
0.9329	High Similarity	NPC170475
0.9329	High Similarity	NPC265480
0.9329	High Similarity	NPC261866
0.9329	High Similarity	NPC149368
0.9272	High Similarity	NPC187379
0.9272	High Similarity	NPC271270
0.9272	High Similarity	NPC473623
0.9272	High Similarity	NPC142860
0.9272	High Similarity	NPC97285
0.9272	High Similarity	NPC153342
0.9272	High Similarity	NPC246469
0.9267	High Similarity	NPC197896
0.9267	High Similarity	NPC156457
0.9267	High Similarity	NPC313163
0.9267	High Similarity	NPC54802
0.9267	High Similarity	NPC133671
0.9267	High Similarity	NPC161749
0.9267	High Similarity	NPC122809
0.9267	High Similarity	NPC135391
0.9267	High Similarity	NPC197304
0.9267	High Similarity	NPC78263
0.9267	High Similarity	NPC258035
0.9267	High Similarity	NPC77672
0.9211	High Similarity	NPC303913
0.9211	High Similarity	NPC129217
0.9211	High Similarity	NPC139320
0.9211	High Similarity	NPC246943
0.9211	High Similarity	NPC265885
0.9211	High Similarity	NPC85707
0.9211	High Similarity	NPC159579
0.9211	High Similarity	NPC215710
0.9211	High Similarity	NPC101636
0.9211	High Similarity	NPC224530
0.9211	High Similarity	NPC163242
0.9211	High Similarity	NPC259957
0.9211	High Similarity	NPC476215
0.9211	High Similarity	NPC473438
0.9211	High Similarity	NPC181465
0.9211	High Similarity	NPC253788
0.9211	High Similarity	NPC276377
0.9211	High Similarity	NPC173582
0.9211	High Similarity	NPC48093
0.9211	High Similarity	NPC216496
0.9211	High Similarity	NPC249281
0.9211	High Similarity	NPC116458
0.9205	High Similarity	NPC308265
0.92	High Similarity	NPC295613
0.92	High Similarity	NPC45165
0.92	High Similarity	NPC473657
0.92	High Similarity	NPC17521
0.915	High Similarity	NPC150164
0.915	High Similarity	NPC475382
0.915	High Similarity	NPC298171
0.915	High Similarity	NPC259834
0.915	High Similarity	NPC44947
0.915	High Similarity	NPC127782
0.915	High Similarity	NPC27942
0.915	High Similarity	NPC300537
0.915	High Similarity	NPC190450
0.915	High Similarity	NPC240306
0.915	High Similarity	NPC473043
0.915	High Similarity	NPC131745
0.9145	High Similarity	NPC271479
0.9145	High Similarity	NPC472320
0.9145	High Similarity	NPC304741
0.9145	High Similarity	NPC136761
0.9145	High Similarity	NPC470405
0.9145	High Similarity	NPC200708
0.9145	High Similarity	NPC471079
0.9139	High Similarity	NPC288084
0.9116	High Similarity	NPC10097
0.9097	High Similarity	NPC150023
0.9091	High Similarity	NPC278419
0.9091	High Similarity	NPC183672
0.9091	High Similarity	NPC121703
0.9091	High Similarity	NPC222936
0.9091	High Similarity	NPC473644
0.9091	High Similarity	NPC179198
0.9091	High Similarity	NPC257566
0.9091	High Similarity	NPC284960
0.9091	High Similarity	NPC309025
0.9091	High Similarity	NPC243930
0.9091	High Similarity	NPC66087
0.9091	High Similarity	NPC311850
0.9091	High Similarity	NPC94777
0.9091	High Similarity	NPC19709
0.9091	High Similarity	NPC124155
0.9091	High Similarity	NPC88023
0.9085	High Similarity	NPC210961
0.9085	High Similarity	NPC477628
0.9085	High Similarity	NPC47923
0.9085	High Similarity	NPC64305
0.9085	High Similarity	NPC170052
0.9085	High Similarity	NPC282169
0.9085	High Similarity	NPC477629
0.9085	High Similarity	NPC470125
0.9085	High Similarity	NPC472994
0.9085	High Similarity	NPC297987
0.9085	High Similarity	NPC270675
0.9085	High Similarity	NPC195685
0.9085	High Similarity	NPC135846
0.9079	High Similarity	NPC43761
0.9079	High Similarity	NPC104677
0.9054	High Similarity	NPC139966
0.9054	High Similarity	NPC307052
0.9048	High Similarity	NPC473133
0.9048	High Similarity	NPC47388
0.9048	High Similarity	NPC470670
0.9048	High Similarity	NPC91902
0.9048	High Similarity	NPC85773
0.9048	High Similarity	NPC302989
0.9032	High Similarity	NPC135358
0.9032	High Similarity	NPC475979
0.9032	High Similarity	NPC294722
0.9032	High Similarity	NPC22832
0.9032	High Similarity	NPC287889
0.9032	High Similarity	NPC139060
0.9032	High Similarity	NPC72016
0.9032	High Similarity	NPC311830
0.9026	High Similarity	NPC77660
0.9026	High Similarity	NPC189142
0.9026	High Similarity	NPC472876
0.902	High Similarity	NPC110349
0.8974	High Similarity	NPC186816
0.8974	High Similarity	NPC262222
0.8974	High Similarity	NPC189564
0.8974	High Similarity	NPC203145
0.8974	High Similarity	NPC99957
0.8974	High Similarity	NPC113968
0.8974	High Similarity	NPC181616
0.8974	High Similarity	NPC5778
0.8974	High Similarity	NPC256188
0.8974	High Similarity	NPC11432
0.8974	High Similarity	NPC12013
0.8974	High Similarity	NPC64425
0.8974	High Similarity	NPC135599
0.8974	High Similarity	NPC236934
0.8974	High Similarity	NPC142142

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 NPC23084 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	299
0.1-0.2	857
0.2-0.3	1865
0.3-0.4	2670
0.4-0.5	1876
0.5-0.6	1039
0.6-0.7	371
0.7-0.8	140
0.8-0.85	30
0.85-0.9	3
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9267	High Similarity	NPD4381	Clinical (unspecified phase)
0.8861	High Similarity	NPD7054	Approved
0.8861	High Similarity	NPD7804	Clinical (unspecified phase)
0.8805	High Similarity	NPD7074	Phase 3
0.8805	High Similarity	NPD7472	Approved
0.875	High Similarity	NPD6797	Phase 2
0.8696	High Similarity	NPD7251	Discontinued
0.869	High Similarity	NPD1552	Clinical (unspecified phase)
0.869	High Similarity	NPD1550	Clinical (unspecified phase)
0.8679	High Similarity	NPD3818	Discontinued
0.8642	High Similarity	NPD7808	Phase 3
0.863	High Similarity	NPD1549	Phase 2
0.8618	High Similarity	NPD4380	Phase 2
0.8528	High Similarity	NPD4338	Clinical (unspecified phase)
0.8526	High Similarity	NPD7075	Discontinued
0.8506	High Similarity	NPD1934	Approved
0.8467	Intermediate Similarity	NPD6799	Approved
0.8466	Intermediate Similarity	NPD6559	Discontinued
0.8452	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8387	Intermediate Similarity	NPD6801	Discontinued
0.8333	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8323	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8323	Intermediate Similarity	NPD6166	Phase 2
0.8323	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8289	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8276	Intermediate Similarity	NPD1240	Approved
0.8224	Intermediate Similarity	NPD1511	Approved
0.8217	Intermediate Similarity	NPD2801	Approved
0.8205	Intermediate Similarity	NPD7411	Suspended
0.8182	Intermediate Similarity	NPD5403	Approved
0.8176	Intermediate Similarity	NPD1510	Phase 2
0.8165	Intermediate Similarity	NPD3817	Phase 2
0.8165	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8163	Intermediate Similarity	NPD1607	Approved
0.8146	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.8141	Intermediate Similarity	NPD6599	Discontinued
0.8133	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8121	Intermediate Similarity	NPD2796	Approved
0.8117	Intermediate Similarity	NPD1512	Approved
0.8113	Intermediate Similarity	NPD3882	Suspended
0.8113	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8052	Intermediate Similarity	NPD5401	Approved
0.8052	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8014	Intermediate Similarity	NPD1091	Approved
0.7987	Intermediate Similarity	NPD7819	Suspended
0.7937	Intermediate Similarity	NPD5402	Approved
0.7914	Intermediate Similarity	NPD6959	Discontinued
0.7898	Intermediate Similarity	NPD1653	Approved
0.7891	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7881	Intermediate Similarity	NPD1551	Phase 2
0.7843	Intermediate Similarity	NPD2800	Approved
0.78	Intermediate Similarity	NPD6651	Approved
0.7792	Intermediate Similarity	NPD4628	Phase 3
0.7771	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7751	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7714	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7707	Intermediate Similarity	NPD2533	Approved
0.7707	Intermediate Similarity	NPD2534	Approved
0.7707	Intermediate Similarity	NPD2532	Approved
0.765	Intermediate Similarity	NPD7584	Approved
0.7636	Intermediate Similarity	NPD5494	Approved
0.7616	Intermediate Similarity	NPD230	Phase 1
0.7616	Intermediate Similarity	NPD8312	Approved
0.7616	Intermediate Similarity	NPD8313	Approved
0.7613	Intermediate Similarity	NPD1243	Approved
0.7613	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7613	Intermediate Similarity	NPD1652	Phase 2
0.761	Intermediate Similarity	NPD920	Approved
0.7586	Intermediate Similarity	NPD9717	Approved
0.7574	Intermediate Similarity	NPD3751	Discontinued
0.7564	Intermediate Similarity	NPD3750	Approved
0.7561	Intermediate Similarity	NPD7768	Phase 2
0.7551	Intermediate Similarity	NPD1203	Approved
0.7546	Intermediate Similarity	NPD1465	Phase 2
0.7546	Intermediate Similarity	NPD8455	Phase 2
0.7545	Intermediate Similarity	NPD3787	Discontinued
0.7545	Intermediate Similarity	NPD6232	Discontinued
0.7529	Intermediate Similarity	NPD5844	Phase 1
0.7517	Intermediate Similarity	NPD422	Phase 1
0.7517	Intermediate Similarity	NPD6832	Phase 2
0.7515	Intermediate Similarity	NPD3749	Approved
0.7515	Intermediate Similarity	NPD7473	Discontinued
0.75	Intermediate Similarity	NPD1933	Approved
0.75	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD7199	Phase 2
0.7484	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7442	Intermediate Similarity	NPD5953	Discontinued
0.7434	Intermediate Similarity	NPD1613	Approved
0.7434	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7427	Intermediate Similarity	NPD7286	Phase 2
0.7419	Intermediate Similarity	NPD2935	Discontinued
0.7418	Intermediate Similarity	NPD6782	Approved
0.7418	Intermediate Similarity	NPD6779	Approved
0.7418	Intermediate Similarity	NPD6778	Approved
0.7418	Intermediate Similarity	NPD6776	Approved
0.7418	Intermediate Similarity	NPD6777	Approved
0.7418	Intermediate Similarity	NPD6780	Approved
0.7418	Intermediate Similarity	NPD6781	Approved
0.7397	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7389	Intermediate Similarity	NPD2654	Approved
0.7386	Intermediate Similarity	NPD447	Suspended
0.738	Intermediate Similarity	NPD8151	Discontinued
0.7378	Intermediate Similarity	NPD37	Approved
0.7368	Intermediate Similarity	NPD7228	Approved
0.7365	Intermediate Similarity	NPD919	Approved
0.7365	Intermediate Similarity	NPD6234	Discontinued
0.7361	Intermediate Similarity	NPD9545	Approved
0.7355	Intermediate Similarity	NPD7033	Discontinued
0.7349	Intermediate Similarity	NPD4967	Phase 2
0.7349	Intermediate Similarity	NPD4966	Approved
0.7349	Intermediate Similarity	NPD4965	Approved
0.7348	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.732	Intermediate Similarity	NPD943	Approved
0.7308	Intermediate Similarity	NPD6100	Approved
0.7308	Intermediate Similarity	NPD6099	Approved
0.7299	Intermediate Similarity	NPD7685	Pre-registration
0.7297	Intermediate Similarity	NPD7435	Discontinued
0.7294	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD1247	Approved
0.7273	Intermediate Similarity	NPD5124	Phase 1
0.7273	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD1019	Discontinued
0.7261	Intermediate Similarity	NPD2344	Approved
0.7257	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7244	Intermediate Similarity	NPD3748	Approved
0.7244	Intermediate Similarity	NPD2799	Discontinued
0.7241	Intermediate Similarity	NPD1548	Phase 1
0.7235	Intermediate Similarity	NPD5710	Approved
0.7235	Intermediate Similarity	NPD5711	Approved
0.7234	Intermediate Similarity	NPD7585	Approved
0.7233	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD9493	Approved
0.7219	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7215	Intermediate Similarity	NPD2424	Discontinued
0.7211	Intermediate Similarity	NPD7783	Phase 2
0.7211	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7205	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7204	Intermediate Similarity	NPD7697	Approved
0.7204	Intermediate Similarity	NPD7698	Approved
0.7204	Intermediate Similarity	NPD7696	Phase 3
0.7195	Intermediate Similarity	NPD7458	Discontinued
0.7193	Intermediate Similarity	NPD3926	Phase 2
0.719	Intermediate Similarity	NPD6798	Discontinued
0.7181	Intermediate Similarity	NPD7583	Approved
0.7171	Intermediate Similarity	NPD4908	Phase 1
0.7171	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7166	Intermediate Similarity	NPD7871	Phase 2
0.7166	Intermediate Similarity	NPD7870	Phase 2
0.7162	Intermediate Similarity	NPD1610	Phase 2
0.7152	Intermediate Similarity	NPD7266	Discontinued
0.7152	Intermediate Similarity	NPD2798	Approved
0.7151	Intermediate Similarity	NPD6823	Phase 2
0.7143	Intermediate Similarity	NPD6233	Phase 2
0.7143	Intermediate Similarity	NPD4360	Phase 2
0.7143	Intermediate Similarity	NPD4363	Phase 3
0.7143	Intermediate Similarity	NPD6534	Approved
0.7143	Intermediate Similarity	NPD7701	Phase 2
0.7143	Intermediate Similarity	NPD6535	Approved
0.7134	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD1241	Discontinued
0.7124	Intermediate Similarity	NPD3027	Phase 3
0.7111	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7108	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD3226	Approved
0.7081	Intermediate Similarity	NPD2309	Approved
0.7078	Intermediate Similarity	NPD2313	Discontinued
0.7078	Intermediate Similarity	NPD411	Approved
0.7078	Intermediate Similarity	NPD3268	Approved
0.7078	Intermediate Similarity	NPD1296	Phase 2
0.7078	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7068	Intermediate Similarity	NPD7874	Approved
0.7068	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD4662	Approved
0.7055	Intermediate Similarity	NPD4661	Approved
0.7052	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7052	Intermediate Similarity	NPD2403	Approved
0.7051	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7051	Intermediate Similarity	NPD6355	Discontinued
0.7039	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD5647	Approved
0.7031	Intermediate Similarity	NPD7801	Approved
0.7027	Intermediate Similarity	NPD7699	Phase 2
0.7027	Intermediate Similarity	NPD7700	Phase 2
0.7025	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD6104	Discontinued
0.7006	Intermediate Similarity	NPD7240	Approved
0.7	Intermediate Similarity	NPD8434	Phase 2
0.6994	Remote Similarity	NPD7390	Discontinued
0.6993	Remote Similarity	NPD9494	Approved
0.6989	Remote Similarity	NPD1729	Discontinued
0.6982	Remote Similarity	NPD5353	Approved
0.6975	Remote Similarity	NPD6190	Approved
0.6974	Remote Similarity	NPD2797	Approved
0.6962	Remote Similarity	NPD7097	Phase 1
0.695	Remote Similarity	NPD290	Approved
0.6937	Remote Similarity	NPD2346	Discontinued
0.6923	Remote Similarity	NPD4062	Phase 3
0.6908	Remote Similarity	NPD3225	Approved

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