NPASS Compound

Structure

CID79908 OpenBabel06191715422D 30 32 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 -0.8660 2.5000 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 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 C 0 0 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 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 -1.7321 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.3301 1.5000 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 -2.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.4641 1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.4641 -0.0000 0.0000 C 0 0 1 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 6.0622 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 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 2.5981 1.5000 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 4.3301 -0.5000 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 -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 8 1 0 0 0 0 2 4 1 0 0 0 0 2 9 2 0 0 0 0 3 5 2 0 0 0 0 3 9 1 0 0 0 0 4 10 2 0 0 0 0 5 10 1 0 0 0 0 6 11 1 0 0 0 0 6 27 1 0 0 0 0 7 28 1 0 0 0 0 8 9 1 0 0 0 0 8 20 2 0 0 0 0 10 29 1 0 0 0 0 11 13 1 0 0 0 0 11 21 1 6 0 0 0 12 7 1 6 0 0 0 12 14 1 0 0 0 0 12 30 1 0 0 0 0 13 16 1 0 0 0 0 13 22 1 1 0 0 0 14 15 1 0 0 0 0 14 23 1 1 0 0 0 15 17 1 0 0 0 0 15 24 1 6 0 0 0 16 18 1 0 0 0 0 16 25 1 6 0 0 0 17 19 1 0 0 0 0 17 26 1 1 0 0 0 18 27 1 0 0 0 0 18 28 1 1 0 0 0 19 29 1 6 0 0 0 19 30 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	430.15
Volume:	397.657
LogP:	-0.995
LogD:	-0.614
LogS:	-1.906
# Rotatable Bonds:	6
TPSA:	175.37
# H-Bond Aceptor:	11
# H-Bond Donor:	6
# Rings:	3
# Heavy Atoms:	11

MedChem Properties

QED Drug-Likeness Score:	0.264
Synthetic Accessibility Score:	4.152
Fsp3:	0.632
Lipinski Rule-of-5:	Rejected
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:	-6.135
MDCK Permeability:	5.109167977934703e-05
Pgp-inhibitor:	0.034
Pgp-substrate:	0.992
Human Intestinal Absorption (HIA):	0.927
20% Bioavailability (F20%):	0.004
30% Bioavailability (F30%):	0.996

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.188
Plasma Protein Binding (PPB):	34.107513427734375%
Volume Distribution (VD):	0.566
Pgp-substrate:	32.99876403808594%

ADMET: Metabolism

CYP1A2-inhibitor:	0.048
CYP1A2-substrate:	0.045
CYP2C19-inhibitor:	0.032
CYP2C19-substrate:	0.096
CYP2C9-inhibitor:	0.002
CYP2C9-substrate:	0.06
CYP2D6-inhibitor:	0.028
CYP2D6-substrate:	0.168
CYP3A4-inhibitor:	0.01
CYP3A4-substrate:	0.017

ADMET: Excretion

Clearance (CL):	1.008
Half-life (T1/2):	0.639

ADMET: Toxicity

hERG Blockers:	0.544
Human Hepatotoxicity (H-HT):	0.032
Drug-inuced Liver Injury (DILI):	0.588
AMES Toxicity:	0.26
Rat Oral Acute Toxicity:	0.092
Maximum Recommended Daily Dose:	0.002
Skin Sensitization:	0.455
Carcinogencity:	0.416
Eye Corrosion:	0.003
Eye Irritation:	0.431
Respiratory Toxicity:	0.029

Download Data

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

Natural Product: NPC79908

Natural Product ID:	NPC79908
*Common Name:**	Asterbatanoside A
IUPAC Name:	1-[4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxymethyl]oxan-2-yl]oxyphenyl]ethanone
Synonyms:
Standard InCHIKey:	YQOKGDRMWQLQNR-BMVMOQKNSA-N
Standard InCHI:	InChI=1S/C19H26O11/c1-8(20)9-2-4-10(5-3-9)29-19-17(26)15(24)14(23)12(30-19)7-28-18-16(25)13(22)11(21)6-27-18/h2-5,11-19,21-26H,6-7H2,1H3/t11-,12-,13+,14-,15+,16-,17-,18+,19-/m1/s1
SMILES:	O[C@@H]1[C@@H](CO[C@@H]2OC[C@H]([C@@H]([C@H]2O)O)O)O[C@H]([C@@H]([C@H]1O)O)Oc1ccc(cc1)C(=O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3402767
PubChem CID:	127686
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]
NPO1254	Cynanchum bungei	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11100	Artemisia capillaris	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1254	Cynanchum bungei	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1254	Cynanchum bungei	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
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	>	2599200.0	nM	PMID[470903]
NPT27	Others	Unspecified		CC50	>	2599200.0	nM	PMID[470903]
NPT963	Organism	Hepatitis B virus	Hepatitis B virus	IC50	=	38500.0	nM	PMID[470903]
NPT2	Others	Unspecified		Selectivity Index	>	67.5	n.a.	PMID[470903]

☑ 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 NPC79908 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	320
0.1-0.2	1292
0.2-0.3	3103
0.3-0.4	7743
0.4-0.5	10643
0.5-0.6	5033
0.6-0.7	7476
0.7-0.8	6421
0.8-0.85	566
0.85-0.9	87
0.9-0.95	10
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9699	High Similarity	NPC294470
0.9559	High Similarity	NPC80098
0.9496	High Similarity	NPC291153
0.9357	High Similarity	NPC474044
0.9333	High Similarity	NPC212729
0.9301	High Similarity	NPC213723
0.9214	High Similarity	NPC471028
0.9097	High Similarity	NPC88886
0.9097	High Similarity	NPC104172
0.9097	High Similarity	NPC182350
0.9091	High Similarity	NPC218685
0.9041	High Similarity	NPC157898
0.9041	High Similarity	NPC137813
0.8973	High Similarity	NPC23253
0.8966	High Similarity	NPC205054
0.8919	High Similarity	NPC99233
0.8919	High Similarity	NPC10205
0.8912	High Similarity	NPC88484
0.8912	High Similarity	NPC259767
0.8904	High Similarity	NPC191154
0.8897	High Similarity	NPC199335
0.8889	High Similarity	NPC473149
0.8859	High Similarity	NPC295613
0.8859	High Similarity	NPC471405
0.8859	High Similarity	NPC170475
0.8859	High Similarity	NPC206378
0.8859	High Similarity	NPC473657
0.8859	High Similarity	NPC45165
0.8851	High Similarity	NPC106625
0.8844	High Similarity	NPC134819
0.8844	High Similarity	NPC36130
0.8844	High Similarity	NPC134905
0.8841	High Similarity	NPC34456
0.8836	High Similarity	NPC227980
0.8828	High Similarity	NPC23084
0.8803	High Similarity	NPC65833
0.8803	High Similarity	NPC31081
0.8803	High Similarity	NPC245219
0.88	High Similarity	NPC65003
0.88	High Similarity	NPC43638
0.88	High Similarity	NPC44931
0.88	High Similarity	NPC473512
0.88	High Similarity	NPC23817
0.88	High Similarity	NPC129827
0.8792	High Similarity	NPC26195
0.8792	High Similarity	NPC72649
0.8792	High Similarity	NPC169248
0.8792	High Similarity	NPC95090
0.8792	High Similarity	NPC39351
0.8792	High Similarity	NPC97052
0.8792	High Similarity	NPC27408
0.8784	High Similarity	NPC121001
0.8784	High Similarity	NPC259182
0.8776	High Similarity	NPC477240
0.8776	High Similarity	NPC214454
0.8776	High Similarity	NPC106025
0.8768	High Similarity	NPC114116
0.8767	High Similarity	NPC111785
0.875	High Similarity	NPC295970
0.875	High Similarity	NPC303913
0.8742	High Similarity	NPC43761
0.8742	High Similarity	NPC73511
0.8742	High Similarity	NPC138811
0.8742	High Similarity	NPC22062
0.8742	High Similarity	NPC473634
0.8741	High Similarity	NPC469367
0.8741	High Similarity	NPC242756
0.8733	High Similarity	NPC127406
0.8733	High Similarity	NPC265480
0.8733	High Similarity	NPC149368
0.8725	High Similarity	NPC194095
0.8725	High Similarity	NPC143851
0.8725	High Similarity	NPC39360
0.8725	High Similarity	NPC83283
0.8725	High Similarity	NPC210003
0.8725	High Similarity	NPC87304
0.8725	High Similarity	NPC268950
0.8725	High Similarity	NPC108706
0.8725	High Similarity	NPC29763
0.8725	High Similarity	NPC327032
0.8725	High Similarity	NPC211158
0.8725	High Similarity	NPC78021
0.8725	High Similarity	NPC191046
0.8716	High Similarity	NPC190217
0.8714	High Similarity	NPC471345
0.8699	High Similarity	NPC472339
0.8696	High Similarity	NPC269421
0.8693	High Similarity	NPC148273
0.8684	High Similarity	NPC153342
0.8684	High Similarity	NPC200708
0.8684	High Similarity	NPC472320
0.8684	High Similarity	NPC142860
0.8684	High Similarity	NPC271270
0.8684	High Similarity	NPC97285
0.8684	High Similarity	NPC271479
0.8684	High Similarity	NPC473623
0.8684	High Similarity	NPC187379
0.8684	High Similarity	NPC246469
0.8675	High Similarity	NPC161749
0.8675	High Similarity	NPC197896
0.8675	High Similarity	NPC108831
0.8675	High Similarity	NPC313163
0.8675	High Similarity	NPC156457
0.8675	High Similarity	NPC6985
0.8675	High Similarity	NPC182634
0.8675	High Similarity	NPC60966
0.8675	High Similarity	NPC258035
0.8667	High Similarity	NPC470604
0.8667	High Similarity	NPC470605
0.8667	High Similarity	NPC470603
0.8649	High Similarity	NPC473966
0.8627	High Similarity	NPC163242
0.8627	High Similarity	NPC265885
0.8627	High Similarity	NPC276377
0.8627	High Similarity	NPC181465
0.8627	High Similarity	NPC215710
0.8627	High Similarity	NPC473438
0.8627	High Similarity	NPC249281
0.8627	High Similarity	NPC253788
0.8627	High Similarity	NPC476215
0.8627	High Similarity	NPC246943
0.8627	High Similarity	NPC116458
0.8627	High Similarity	NPC173582
0.8627	High Similarity	NPC139320
0.8627	High Similarity	NPC101636
0.8618	High Similarity	NPC320283
0.8618	High Similarity	NPC472459
0.8618	High Similarity	NPC308265
0.8618	High Similarity	NPC41121
0.8618	High Similarity	NPC111929
0.8611	High Similarity	NPC478250
0.8609	High Similarity	NPC203500
0.8609	High Similarity	NPC323593
0.8609	High Similarity	NPC307938
0.8609	High Similarity	NPC17521
0.8591	High Similarity	NPC289438
0.8571	High Similarity	NPC259834
0.8571	High Similarity	NPC44947
0.8571	High Similarity	NPC190450
0.8571	High Similarity	NPC240306
0.8571	High Similarity	NPC471029
0.8571	High Similarity	NPC475382
0.8571	High Similarity	NPC472876
0.8571	High Similarity	NPC298171
0.8571	High Similarity	NPC244875
0.8562	High Similarity	NPC471079
0.8562	High Similarity	NPC136761
0.8562	High Similarity	NPC203020
0.8562	High Similarity	NPC470405
0.8562	High Similarity	NPC304741
0.8562	High Similarity	NPC239966
0.8553	High Similarity	NPC133984
0.8553	High Similarity	NPC54802
0.8553	High Similarity	NPC122809
0.8553	High Similarity	NPC135391
0.8553	High Similarity	NPC470606
0.8553	High Similarity	NPC78263
0.8553	High Similarity	NPC197304
0.8553	High Similarity	NPC133671
0.8553	High Similarity	NPC77672
0.8552	High Similarity	NPC473281
0.8552	High Similarity	NPC77922
0.8542	High Similarity	NPC184053
0.8523	High Similarity	NPC38775
0.8516	High Similarity	NPC257566
0.8516	High Similarity	NPC473644
0.8516	High Similarity	NPC311850
0.8516	High Similarity	NPC124155
0.8507	High Similarity	NPC476142
0.8506	High Similarity	NPC47923
0.8506	High Similarity	NPC85707
0.8506	High Similarity	NPC182045
0.8506	High Similarity	NPC210961
0.8506	High Similarity	NPC472994
0.8506	High Similarity	NPC477629
0.8506	High Similarity	NPC297987
0.8506	High Similarity	NPC224530
0.8506	High Similarity	NPC195685
0.8506	High Similarity	NPC216496
0.8506	High Similarity	NPC170052
0.8506	High Similarity	NPC64305
0.8506	High Similarity	NPC477628
0.8506	High Similarity	NPC259957
0.8506	High Similarity	NPC159579
0.8506	High Similarity	NPC48093
0.8506	High Similarity	NPC270675
0.8506	High Similarity	NPC129217
0.8506	High Similarity	NPC135846
0.8497	Intermediate Similarity	NPC470607
0.8497	Intermediate Similarity	NPC289811
0.8497	Intermediate Similarity	NPC160780
0.8487	Intermediate Similarity	NPC261866
0.8483	Intermediate Similarity	NPC475213
0.8483	Intermediate Similarity	NPC152796
0.8477	Intermediate Similarity	NPC478232
0.8462	Intermediate Similarity	NPC475366
0.8462	Intermediate Similarity	NPC475979
0.8462	Intermediate Similarity	NPC139060
0.8462	Intermediate Similarity	NPC135358
0.8462	Intermediate Similarity	NPC475497

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 NPC79908 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	282
0.1-0.2	790
0.2-0.3	1518
0.3-0.4	2648
0.4-0.5	2157
0.5-0.6	1150
0.6-0.7	479
0.7-0.8	122
0.8-0.85	4
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8675	High Similarity	NPD4381	Clinical (unspecified phase)
0.8302	Intermediate Similarity	NPD7054	Approved
0.8302	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8288	Intermediate Similarity	NPD4628	Phase 3
0.825	Intermediate Similarity	NPD7074	Phase 3
0.825	Intermediate Similarity	NPD7472	Approved
0.8199	Intermediate Similarity	NPD6797	Phase 2
0.8148	Intermediate Similarity	NPD7251	Discontinued
0.8125	Intermediate Similarity	NPD3818	Discontinued
0.8098	Intermediate Similarity	NPD7808	Phase 3
0.8039	Intermediate Similarity	NPD4380	Phase 2
0.8	Intermediate Similarity	NPD8455	Phase 2
0.8	Intermediate Similarity	NPD6799	Approved
0.8	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7973	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7962	Intermediate Similarity	NPD7075	Discontinued
0.7935	Intermediate Similarity	NPD6801	Discontinued
0.7927	Intermediate Similarity	NPD6559	Discontinued
0.7905	Intermediate Similarity	NPD1549	Phase 2
0.7899	Intermediate Similarity	NPD1091	Approved
0.7879	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7838	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7838	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7821	Intermediate Similarity	NPD1934	Approved
0.7785	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD6166	Phase 2
0.7771	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.777	Intermediate Similarity	NPD2796	Approved
0.7756	Intermediate Similarity	NPD7411	Suspended
0.7727	Intermediate Similarity	NPD5403	Approved
0.7727	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7724	Intermediate Similarity	NPD6233	Phase 2
0.7722	Intermediate Similarity	NPD3817	Phase 2
0.7718	Intermediate Similarity	NPD7266	Discontinued
0.7712	Intermediate Similarity	NPD5401	Approved
0.7711	Intermediate Similarity	NPD7685	Pre-registration
0.7692	Intermediate Similarity	NPD6599	Discontinued
0.7658	Intermediate Similarity	NPD7819	Suspended
0.7655	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.763	Intermediate Similarity	NPD1241	Discontinued
0.7619	Intermediate Similarity	NPD8312	Approved
0.7619	Intermediate Similarity	NPD8313	Approved
0.7609	Intermediate Similarity	NPD9545	Approved
0.7597	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7564	Intermediate Similarity	NPD1653	Approved
0.7547	Intermediate Similarity	NPD2801	Approved
0.7545	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7534	Intermediate Similarity	NPD6798	Discontinued
0.7516	Intermediate Similarity	NPD7458	Discontinued
0.75	Intermediate Similarity	NPD5402	Approved
0.75	Intermediate Similarity	NPD1933	Approved
0.75	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7467	Intermediate Similarity	NPD1510	Phase 2
0.7453	Intermediate Similarity	NPD3882	Suspended
0.7451	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7432	Intermediate Similarity	NPD3140	Approved
0.7432	Intermediate Similarity	NPD3142	Approved
0.7432	Intermediate Similarity	NPD1240	Approved
0.7425	Intermediate Similarity	NPD5844	Phase 1
0.7423	Intermediate Similarity	NPD5494	Approved
0.7419	Intermediate Similarity	NPD1511	Approved
0.7414	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7403	Intermediate Similarity	NPD2354	Approved
0.7403	Intermediate Similarity	NPD3887	Approved
0.74	Intermediate Similarity	NPD7097	Phase 1
0.7397	Intermediate Similarity	NPD6832	Phase 2
0.7394	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD1652	Phase 2
0.7378	Intermediate Similarity	NPD7199	Phase 2
0.7365	Intermediate Similarity	NPD4062	Phase 3
0.7365	Intermediate Similarity	NPD3751	Discontinued
0.7351	Intermediate Similarity	NPD7033	Discontinued
0.7343	Intermediate Similarity	NPD3972	Approved
0.7338	Intermediate Similarity	NPD3750	Approved
0.7333	Intermediate Similarity	NPD1607	Approved
0.7333	Intermediate Similarity	NPD3787	Discontinued
0.7329	Intermediate Similarity	NPD9494	Approved
0.7325	Intermediate Similarity	NPD1512	Approved
0.732	Intermediate Similarity	NPD2424	Discontinued
0.731	Intermediate Similarity	NPD1049	Clinical (unspecified phase)
0.7299	Intermediate Similarity	NPD7843	Approved
0.729	Intermediate Similarity	NPD6190	Approved
0.7273	Intermediate Similarity	NPD6959	Discontinued
0.7267	Intermediate Similarity	NPD6355	Discontinued
0.7267	Intermediate Similarity	NPD230	Phase 1
0.726	Intermediate Similarity	NPD2798	Approved
0.726	Intermediate Similarity	NPD5647	Approved
0.7259	Intermediate Similarity	NPD2684	Approved
0.7246	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7244	Intermediate Similarity	NPD5058	Phase 3
0.7237	Intermediate Similarity	NPD2799	Discontinued
0.7237	Intermediate Similarity	NPD3748	Approved
0.7225	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD9717	Approved
0.7222	Intermediate Similarity	NPD1608	Approved
0.7222	Intermediate Similarity	NPD1465	Phase 2
0.7186	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7185	Intermediate Similarity	NPD1358	Approved
0.7181	Intermediate Similarity	NPD2313	Discontinued
0.7181	Intermediate Similarity	NPD3268	Approved
0.7174	Intermediate Similarity	NPD7584	Approved
0.716	Intermediate Similarity	NPD7228	Approved
0.716	Intermediate Similarity	NPD37	Approved
0.7152	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD2353	Approved
0.7143	Intermediate Similarity	NPD7157	Approved
0.7143	Intermediate Similarity	NPD2355	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD4966	Approved
0.7134	Intermediate Similarity	NPD7440	Discontinued
0.7134	Intermediate Similarity	NPD4965	Approved
0.7134	Intermediate Similarity	NPD4967	Phase 2
0.7127	Intermediate Similarity	NPD6778	Approved
0.7127	Intermediate Similarity	NPD6780	Approved
0.7127	Intermediate Similarity	NPD6782	Approved
0.7127	Intermediate Similarity	NPD6776	Approved
0.7127	Intermediate Similarity	NPD6781	Approved
0.7127	Intermediate Similarity	NPD6777	Approved
0.7127	Intermediate Similarity	NPD6779	Approved
0.7113	Intermediate Similarity	NPD1894	Discontinued
0.7107	Intermediate Similarity	NPD6273	Approved
0.7097	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD8434	Phase 2
0.7081	Intermediate Similarity	NPD7583	Approved
0.7081	Intermediate Similarity	NPD3226	Approved
0.7078	Intermediate Similarity	NPD1551	Phase 2
0.7078	Intermediate Similarity	NPD2935	Discontinued
0.7075	Intermediate Similarity	NPD1203	Approved
0.7075	Intermediate Similarity	NPD2797	Approved
0.7063	Intermediate Similarity	NPD920	Approved
0.7059	Intermediate Similarity	NPD4538	Approved
0.7059	Intermediate Similarity	NPD290	Approved
0.7059	Intermediate Similarity	NPD4536	Approved
0.7059	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7051	Intermediate Similarity	NPD6674	Discontinued
0.7048	Intermediate Similarity	NPD6234	Discontinued
0.7044	Intermediate Similarity	NPD4661	Approved
0.7044	Intermediate Similarity	NPD4662	Approved
0.7043	Intermediate Similarity	NPD7585	Approved
0.7039	Intermediate Similarity	NPD447	Suspended
0.7039	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD5124	Phase 1
0.7039	Intermediate Similarity	NPD4340	Discontinued
0.7035	Intermediate Similarity	NPD3823	Discontinued
0.7032	Intermediate Similarity	NPD2346	Discontinued
0.7032	Intermediate Similarity	NPD2344	Approved
0.703	Intermediate Similarity	NPD7768	Phase 2
0.7027	Intermediate Similarity	NPD1019	Discontinued
0.7014	Intermediate Similarity	NPD17	Approved
0.7013	Intermediate Similarity	NPD4308	Phase 3
0.7011	Intermediate Similarity	NPD7696	Phase 3
0.7011	Intermediate Similarity	NPD7697	Approved
0.7011	Intermediate Similarity	NPD7435	Discontinued
0.7011	Intermediate Similarity	NPD7698	Approved
0.7007	Intermediate Similarity	NPD3225	Approved
0.7006	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD5049	Phase 3
0.6994	Remote Similarity	NPD7240	Approved
0.6994	Remote Similarity	NPD6386	Approved
0.6994	Remote Similarity	NPD6385	Approved
0.6993	Remote Similarity	NPD6653	Approved
0.6988	Remote Similarity	NPD3749	Approved
0.6986	Remote Similarity	NPD1481	Phase 2
0.6985	Remote Similarity	NPD3134	Approved
0.6975	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6974	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6974	Remote Similarity	NPD1613	Approved
0.697	Remote Similarity	NPD5353	Approved
0.6968	Remote Similarity	NPD2240	Approved
0.6968	Remote Similarity	NPD2239	Approved
0.6964	Remote Similarity	NPD8127	Discontinued
0.6959	Remote Similarity	NPD3267	Approved
0.6959	Remote Similarity	NPD3266	Approved
0.6954	Remote Similarity	NPD3764	Approved
0.6952	Remote Similarity	NPD7701	Phase 2
0.6951	Remote Similarity	NPD7577	Discontinued
0.6951	Remote Similarity	NPD6844	Discontinued
0.6943	Remote Similarity	NPD2800	Approved
0.6943	Remote Similarity	NPD1243	Approved
0.6937	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6937	Remote Similarity	NPD8389	Clinical (unspecified phase)
0.6931	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6931	Remote Similarity	NPD7783	Phase 2
0.6928	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD6005	Phase 3
0.6923	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD6232	Discontinued
0.6923	Remote Similarity	NPD6002	Phase 3
0.6923	Remote Similarity	NPD6004	Phase 3
0.6923	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD5536	Phase 2
0.6923	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD3705	Approved
0.6918	Remote Similarity	NPD422	Phase 1
0.6918	Remote Similarity	NPD1535	Discovery
0.6918	Remote Similarity	NPD643	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