NPASS Compound

Structure

NPC473164 OpenBabel07101719132D 36 39 0 0 1 0 0 0 0 0999 V2000 1.4205 -3.4156 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0456 2.3069 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0206 2.3069 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8613 -2.9979 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6586 -3.9516 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6887 -0.9750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4478 0.4032 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6887 0.9750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.9500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8444 -1.4625 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3775 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5331 -0.4875 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0266 -2.8938 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8444 1.4625 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7717 -0.1862 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0729 -2.6911 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8444 -1.4625 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3279 -3.8211 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.3447 -0.9750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8444 -0.4875 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6887 0.9750 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.3775 0.9750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 0.9750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7717 -1.7638 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2816 -4.0238 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5331 1.4625 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9340 -3.2992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6887 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8444 -0.4875 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.6755 -4.5456 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3197 -0.9750 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2219 1.4625 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8444 1.4625 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.5829 -4.9511 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.6327 -2.3719 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 26 1 0 0 0 0 3 26 1 0 0 0 0 4 27 1 0 0 0 0 5 27 1 0 0 0 0 7 29 1 0 0 0 0 9 10 2 0 0 0 0 9 17 1 0 0 0 0 10 20 1 0 0 0 0 11 12 1 0 0 0 0 11 22 1 0 0 0 0 12 28 1 0 0 0 0 13 16 1 0 0 0 0 13 18 1 0 0 0 0 14 21 1 0 0 0 0 14 23 1 0 0 0 0 15 19 1 0 0 0 0 15 29 1 0 0 0 0 16 1 1 1 0 0 0 16 24 1 0 0 0 0 17 24 2 0 0 0 0 17 29 1 0 0 0 0 18 25 1 0 0 0 0 18 31 1 1 0 0 0 19 24 1 0 0 0 0 19 32 2 0 0 0 0 20 28 1 1 0 0 0 20 30 1 0 0 0 0 21 26 1 0 0 0 0 21 28 1 6 0 0 0 22 26 1 0 0 0 0 22 33 2 0 0 0 0 23 30 1 0 0 0 0 23 34 2 0 0 0 0 25 27 1 0 0 0 0 25 35 1 1 0 0 0 27 36 1 0 0 0 0 28 6 1 6 0 0 0 29 30 1 1 0 0 0 30 8 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	500.31
Volume:	532.769
LogP:	2.605
LogD:	2.555
LogS:	-4.015
# Rotatable Bonds:	5
TPSA:	111.9
# H-Bond Aceptor:	6
# H-Bond Donor:	3
# Rings:	4
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.527
Synthetic Accessibility Score:	5.367
Fsp3:	0.767
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.282
MDCK Permeability:	3.249128712923266e-05
Pgp-inhibitor:	0.997
Pgp-substrate:	0.845
Human Intestinal Absorption (HIA):	0.02
20% Bioavailability (F20%):	0.05
30% Bioavailability (F30%):	0.685

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.991
Plasma Protein Binding (PPB):	83.90617370605469%
Volume Distribution (VD):	0.607
Pgp-substrate:	11.994011878967285%

ADMET: Metabolism

CYP1A2-inhibitor:	0.002
CYP1A2-substrate:	0.533
CYP2C19-inhibitor:	0.022
CYP2C19-substrate:	0.796
CYP2C9-inhibitor:	0.035
CYP2C9-substrate:	0.049
CYP2D6-inhibitor:	0.002
CYP2D6-substrate:	0.017
CYP3A4-inhibitor:	0.652
CYP3A4-substrate:	0.918

ADMET: Excretion

Clearance (CL):	7.568
Half-life (T1/2):	0.463

ADMET: Toxicity

hERG Blockers:	0.004
Human Hepatotoxicity (H-HT):	0.176
Drug-inuced Liver Injury (DILI):	0.066
AMES Toxicity:	0.021
Rat Oral Acute Toxicity:	0.486
Maximum Recommended Daily Dose:	0.942
Skin Sensitization:	0.158
Carcinogencity:	0.837
Eye Corrosion:	0.004
Eye Irritation:	0.011
Respiratory Toxicity:	0.987

Download Data

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

Natural Product: NPC473164

Natural Product ID:	NPC473164
*Common Name:**	MERCJFBNQLQGLG-BFAYCBBUSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	MERCJFBNQLQGLG-BFAYCBBUSA-N
Standard InCHI:	InChI=1S/C30H44O6/c1-16(13-18(31)25(35)27(4,5)36)24-17-9-10-20-28(6)12-11-22(33)26(2,3)21(28)14-23(34)30(20,8)29(17,7)15-19(24)32/h9-10,16,18,20-21,25,31,35-36H,11-15H2,1-8H3/t16-,18+,20+,21+,25+,28-,29+,30-/m1/s1
SMILES:	CC(CC(C(C(C)(C)O)O)O)C1=C2C=CC3C4(CCC(=O)C(C4CC(=O)C3(C2(CC1=O)C)C)(C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3632944
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids

*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
NPO30648	Alisma orientale	Species	Alismataceae	Eukaryota	rhizome	n.a.	n.a.	PMID[10560729]
NPO30648	Alisma orientale	Species	Alismataceae	Eukaryota	n.a.	rhizome	n.a.	PMID[17541191]
NPO30648	Alisma orientale	Species	Alismataceae	Eukaryota	Rhizome	n.a.	n.a.	PMID[26425784]
NPO30648	Alisma orientale	Species	Alismataceae	Eukaryota	n.a.	tuber	n.a.	PMID[26666273]
NPO30648	Alisma orientale	Species	Alismataceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]

☑ 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
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT203	Individual Protein	Carboxylesterase 2	Homo sapiens	IC50	=	100000.0	nM	PMID[493189]

☑ 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 NPC473164 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	189
0.1-0.2	1002
0.2-0.3	4268
0.3-0.4	10471
0.4-0.5	12704
0.5-0.6	7213
0.6-0.7	5418
0.7-0.8	1366
0.8-0.85	60
0.85-0.9	0
0.9-0.95	4
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9775	High Similarity	NPC473172
0.9247	High Similarity	NPC473161
0.913	High Similarity	NPC473162
0.9062	High Similarity	NPC473163
0.9032	High Similarity	NPC473170
0.871	High Similarity	NPC19114
0.8681	High Similarity	NPC90652
0.8587	High Similarity	NPC470417
0.8587	High Similarity	NPC44181
0.8571	High Similarity	NPC473168
0.8511	High Similarity	NPC473167
0.8478	Intermediate Similarity	NPC99909
0.8454	Intermediate Similarity	NPC474785
0.8454	Intermediate Similarity	NPC474938
0.8444	Intermediate Similarity	NPC86370
0.84	Intermediate Similarity	NPC239716
0.8387	Intermediate Similarity	NPC292491
0.8387	Intermediate Similarity	NPC310752
0.8384	Intermediate Similarity	NPC473174
0.837	Intermediate Similarity	NPC89077
0.8367	Intermediate Similarity	NPC471582
0.8352	Intermediate Similarity	NPC85774
0.8352	Intermediate Similarity	NPC214043
0.8298	Intermediate Similarity	NPC477943
0.8298	Intermediate Similarity	NPC32830
0.8298	Intermediate Similarity	NPC31985
0.8298	Intermediate Similarity	NPC1015
0.828	Intermediate Similarity	NPC58063
0.828	Intermediate Similarity	NPC136548
0.828	Intermediate Similarity	NPC141292
0.8261	Intermediate Similarity	NPC469948
0.8247	Intermediate Similarity	NPC180950
0.8247	Intermediate Similarity	NPC280725
0.8229	Intermediate Similarity	NPC233118
0.8229	Intermediate Similarity	NPC474736
0.8229	Intermediate Similarity	NPC472930
0.8229	Intermediate Similarity	NPC474807
0.8222	Intermediate Similarity	NPC121984
0.8211	Intermediate Similarity	NPC129913
0.8191	Intermediate Similarity	NPC158778
0.8191	Intermediate Similarity	NPC328539
0.8182	Intermediate Similarity	NPC471717
0.8172	Intermediate Similarity	NPC145879
0.8172	Intermediate Similarity	NPC474733
0.8172	Intermediate Similarity	NPC474778
0.8172	Intermediate Similarity	NPC474732
0.8172	Intermediate Similarity	NPC31564
0.8172	Intermediate Similarity	NPC327115
0.8163	Intermediate Similarity	NPC249954
0.8163	Intermediate Similarity	NPC471463
0.8155	Intermediate Similarity	NPC185
0.8152	Intermediate Similarity	NPC58841
0.8152	Intermediate Similarity	NPC473246
0.8152	Intermediate Similarity	NPC161423
0.8152	Intermediate Similarity	NPC227064
0.8152	Intermediate Similarity	NPC329043
0.8152	Intermediate Similarity	NPC321187
0.8144	Intermediate Similarity	NPC472977
0.8144	Intermediate Similarity	NPC472976
0.8144	Intermediate Similarity	NPC474690
0.8144	Intermediate Similarity	NPC67831
0.8144	Intermediate Similarity	NPC471207
0.8144	Intermediate Similarity	NPC318332
0.8144	Intermediate Similarity	NPC299100
0.8144	Intermediate Similarity	NPC174051
0.8144	Intermediate Similarity	NPC8993
0.8132	Intermediate Similarity	NPC212083
0.8125	Intermediate Similarity	NPC168027
0.8125	Intermediate Similarity	NPC185936
0.8125	Intermediate Similarity	NPC262870
0.8125	Intermediate Similarity	NPC472978
0.8125	Intermediate Similarity	NPC475806
0.8125	Intermediate Similarity	NPC155304
0.8119	Intermediate Similarity	NPC477915
0.8119	Intermediate Similarity	NPC87351
0.8111	Intermediate Similarity	NPC2482
0.8105	Intermediate Similarity	NPC86319
0.8105	Intermediate Similarity	NPC326627
0.8105	Intermediate Similarity	NPC310010
0.8105	Intermediate Similarity	NPC275740
0.8105	Intermediate Similarity	NPC184663
0.8105	Intermediate Similarity	NPC186688
0.81	Intermediate Similarity	NPC110149
0.81	Intermediate Similarity	NPC144956
0.8085	Intermediate Similarity	NPC93778
0.8085	Intermediate Similarity	NPC241875
0.8085	Intermediate Similarity	NPC475740
0.8085	Intermediate Similarity	NPC469314
0.8085	Intermediate Similarity	NPC469317
0.8081	Intermediate Similarity	NPC18509
0.8081	Intermediate Similarity	NPC161147
0.8065	Intermediate Similarity	NPC470574
0.8061	Intermediate Similarity	NPC259286
0.8061	Intermediate Similarity	NPC472932
0.8061	Intermediate Similarity	NPC88310
0.8043	Intermediate Similarity	NPC64600
0.8041	Intermediate Similarity	NPC134826
0.8039	Intermediate Similarity	NPC264048
0.8039	Intermediate Similarity	NPC475050
0.8039	Intermediate Similarity	NPC311612
0.8021	Intermediate Similarity	NPC85173
0.8021	Intermediate Similarity	NPC320026
0.8021	Intermediate Similarity	NPC171441
0.8	Intermediate Similarity	NPC472730
0.8	Intermediate Similarity	NPC474113
0.8	Intermediate Similarity	NPC214644
0.8	Intermediate Similarity	NPC153776
0.8	Intermediate Similarity	NPC147954
0.8	Intermediate Similarity	NPC131470
0.8	Intermediate Similarity	NPC472729
0.8	Intermediate Similarity	NPC177680
0.8	Intermediate Similarity	NPC41405
0.8	Intermediate Similarity	NPC143767
0.7981	Intermediate Similarity	NPC473169
0.7981	Intermediate Similarity	NPC165873
0.7981	Intermediate Similarity	NPC83744
0.7981	Intermediate Similarity	NPC477916
0.798	Intermediate Similarity	NPC471153
0.798	Intermediate Similarity	NPC49371
0.798	Intermediate Similarity	NPC473158
0.7979	Intermediate Similarity	NPC118648
0.7979	Intermediate Similarity	NPC222613
0.7979	Intermediate Similarity	NPC475022
0.7979	Intermediate Similarity	NPC158393
0.7979	Intermediate Similarity	NPC94666
0.7978	Intermediate Similarity	NPC325946
0.7961	Intermediate Similarity	NPC209502
0.7961	Intermediate Similarity	NPC255309
0.7961	Intermediate Similarity	NPC204833
0.7961	Intermediate Similarity	NPC473175
0.7959	Intermediate Similarity	NPC49670
0.7957	Intermediate Similarity	NPC82902
0.7957	Intermediate Similarity	NPC473157
0.7957	Intermediate Similarity	NPC237712
0.7957	Intermediate Similarity	NPC476412
0.7957	Intermediate Similarity	NPC59453
0.7957	Intermediate Similarity	NPC221758
0.7941	Intermediate Similarity	NPC473424
0.7941	Intermediate Similarity	NPC473928
0.7938	Intermediate Similarity	NPC131872
0.7938	Intermediate Similarity	NPC473998
0.7938	Intermediate Similarity	NPC272746
0.7935	Intermediate Similarity	NPC469325
0.7935	Intermediate Similarity	NPC151519
0.7925	Intermediate Similarity	NPC5284
0.7921	Intermediate Similarity	NPC472728
0.7921	Intermediate Similarity	NPC51370
0.7921	Intermediate Similarity	NPC472727
0.7921	Intermediate Similarity	NPC287833
0.7921	Intermediate Similarity	NPC474720
0.7921	Intermediate Similarity	NPC316964
0.7917	Intermediate Similarity	NPC250592
0.7917	Intermediate Similarity	NPC119416
0.7917	Intermediate Similarity	NPC77263
0.7917	Intermediate Similarity	NPC474245
0.7917	Intermediate Similarity	NPC469319
0.7917	Intermediate Similarity	NPC26959
0.7917	Intermediate Similarity	NPC229871
0.7917	Intermediate Similarity	NPC309603
0.7917	Intermediate Similarity	NPC472973
0.7917	Intermediate Similarity	NPC473999
0.7917	Intermediate Similarity	NPC268406
0.7917	Intermediate Similarity	NPC2983
0.7905	Intermediate Similarity	NPC329417
0.79	Intermediate Similarity	NPC472074
0.79	Intermediate Similarity	NPC472073
0.79	Intermediate Similarity	NPC43747
0.7895	Intermediate Similarity	NPC287079
0.7895	Intermediate Similarity	NPC317590
0.7895	Intermediate Similarity	NPC469322
0.7885	Intermediate Similarity	NPC97202
0.7885	Intermediate Similarity	NPC149047
0.7885	Intermediate Similarity	NPC150531
0.7885	Intermediate Similarity	NPC171137
0.7885	Intermediate Similarity	NPC152695
0.7885	Intermediate Similarity	NPC49958
0.7885	Intermediate Similarity	NPC260268
0.7885	Intermediate Similarity	NPC302607
0.7885	Intermediate Similarity	NPC96377
0.7885	Intermediate Similarity	NPC202167
0.7885	Intermediate Similarity	NPC48733
0.7885	Intermediate Similarity	NPC214264
0.7885	Intermediate Similarity	NPC476027
0.7885	Intermediate Similarity	NPC296945
0.7885	Intermediate Similarity	NPC319077
0.7885	Intermediate Similarity	NPC85829
0.7885	Intermediate Similarity	NPC50692
0.7879	Intermediate Similarity	NPC472824
0.7879	Intermediate Similarity	NPC200702
0.7879	Intermediate Similarity	NPC139459
0.7872	Intermediate Similarity	NPC476426
0.7872	Intermediate Similarity	NPC471224
0.7872	Intermediate Similarity	NPC474218
0.7864	Intermediate Similarity	NPC111323
0.7864	Intermediate Similarity	NPC191892
0.7864	Intermediate Similarity	NPC117185
0.7857	Intermediate Similarity	NPC250575
0.7857	Intermediate Similarity	NPC109305
0.7857	Intermediate Similarity	NPC69454
0.7857	Intermediate Similarity	NPC472942

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 NPC473164 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	169
0.1-0.2	1247
0.2-0.3	3774
0.3-0.4	2658
0.4-0.5	824
0.5-0.6	195
0.6-0.7	160
0.7-0.8	119
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
0.8316	Intermediate Similarity	NPD6079	Approved
0.8298	Intermediate Similarity	NPD5328	Approved
0.8247	Intermediate Similarity	NPD4629	Approved
0.8247	Intermediate Similarity	NPD5210	Approved
0.8152	Intermediate Similarity	NPD3133	Approved
0.8152	Intermediate Similarity	NPD3665	Phase 1
0.8152	Intermediate Similarity	NPD3666	Approved
0.8105	Intermediate Similarity	NPD4753	Phase 2
0.81	Intermediate Similarity	NPD5286	Approved
0.81	Intermediate Similarity	NPD4696	Approved
0.81	Intermediate Similarity	NPD5285	Approved
0.8081	Intermediate Similarity	NPD4755	Approved
0.798	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.798	Intermediate Similarity	NPD5222	Approved
0.798	Intermediate Similarity	NPD5221	Approved
0.7979	Intermediate Similarity	NPD5279	Phase 3
0.7979	Intermediate Similarity	NPD3618	Phase 1
0.7957	Intermediate Similarity	NPD4786	Approved
0.7941	Intermediate Similarity	NPD5226	Approved
0.7941	Intermediate Similarity	NPD4633	Approved
0.7941	Intermediate Similarity	NPD5211	Phase 2
0.7941	Intermediate Similarity	NPD5224	Approved
0.7941	Intermediate Similarity	NPD5225	Approved
0.7935	Intermediate Similarity	NPD3667	Approved
0.7921	Intermediate Similarity	NPD4700	Approved
0.79	Intermediate Similarity	NPD5173	Approved
0.7864	Intermediate Similarity	NPD5175	Approved
0.7864	Intermediate Similarity	NPD5174	Approved
0.7843	Intermediate Similarity	NPD5223	Approved
0.78	Intermediate Similarity	NPD4697	Phase 3
0.7788	Intermediate Similarity	NPD5141	Approved
0.7757	Intermediate Similarity	NPD4634	Approved
0.7742	Intermediate Similarity	NPD4223	Phase 3
0.7742	Intermediate Similarity	NPD4221	Approved
0.7736	Intermediate Similarity	NPD6899	Approved
0.7736	Intermediate Similarity	NPD6881	Approved
0.7723	Intermediate Similarity	NPD6083	Phase 2
0.7723	Intermediate Similarity	NPD6084	Phase 2
0.7714	Intermediate Similarity	NPD5739	Approved
0.7714	Intermediate Similarity	NPD7128	Approved
0.7714	Intermediate Similarity	NPD6675	Approved
0.7714	Intermediate Similarity	NPD6402	Approved
0.7684	Intermediate Similarity	NPD5329	Approved
0.7677	Intermediate Similarity	NPD4202	Approved
0.7647	Intermediate Similarity	NPD5696	Approved
0.7642	Intermediate Similarity	NPD5697	Approved
0.7615	Intermediate Similarity	NPD8297	Approved
0.7604	Intermediate Similarity	NPD5280	Approved
0.7604	Intermediate Similarity	NPD4519	Discontinued
0.7604	Intermediate Similarity	NPD4623	Approved
0.7604	Intermediate Similarity	NPD4694	Approved
0.7593	Intermediate Similarity	NPD7290	Approved
0.7593	Intermediate Similarity	NPD7102	Approved
0.7593	Intermediate Similarity	NPD6883	Approved
0.7579	Intermediate Similarity	NPD4197	Approved
0.7576	Intermediate Similarity	NPD5281	Approved
0.7576	Intermediate Similarity	NPD7515	Phase 2
0.7576	Intermediate Similarity	NPD5284	Approved
0.757	Intermediate Similarity	NPD4730	Approved
0.757	Intermediate Similarity	NPD4729	Approved
0.757	Intermediate Similarity	NPD7320	Approved
0.7547	Intermediate Similarity	NPD4768	Approved
0.7547	Intermediate Similarity	NPD4767	Approved
0.7524	Intermediate Similarity	NPD4754	Approved
0.7523	Intermediate Similarity	NPD8130	Phase 1
0.7523	Intermediate Similarity	NPD6617	Approved
0.7523	Intermediate Similarity	NPD6650	Approved
0.7523	Intermediate Similarity	NPD6869	Approved
0.7523	Intermediate Similarity	NPD6649	Approved
0.7523	Intermediate Similarity	NPD6847	Approved
0.75	Intermediate Similarity	NPD6013	Approved
0.75	Intermediate Similarity	NPD6373	Approved
0.75	Intermediate Similarity	NPD6372	Approved
0.75	Intermediate Similarity	NPD6012	Approved
0.75	Intermediate Similarity	NPD6014	Approved
0.7477	Intermediate Similarity	NPD6412	Phase 2
0.7477	Intermediate Similarity	NPD5701	Approved
0.7455	Intermediate Similarity	NPD6882	Approved
0.7431	Intermediate Similarity	NPD5248	Approved
0.7431	Intermediate Similarity	NPD5250	Approved
0.7431	Intermediate Similarity	NPD5251	Approved
0.7431	Intermediate Similarity	NPD5247	Approved
0.7431	Intermediate Similarity	NPD5249	Phase 3
0.7423	Intermediate Similarity	NPD4689	Approved
0.7423	Intermediate Similarity	NPD5330	Approved
0.7423	Intermediate Similarity	NPD6409	Approved
0.7423	Intermediate Similarity	NPD5690	Phase 2
0.7423	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7423	Intermediate Similarity	NPD4138	Approved
0.7423	Intermediate Similarity	NPD7521	Approved
0.7423	Intermediate Similarity	NPD6684	Approved
0.7423	Intermediate Similarity	NPD4690	Approved
0.7423	Intermediate Similarity	NPD7334	Approved
0.7423	Intermediate Similarity	NPD7146	Approved
0.7423	Intermediate Similarity	NPD4688	Approved
0.7423	Intermediate Similarity	NPD4693	Phase 3
0.7423	Intermediate Similarity	NPD5205	Approved
0.7407	Intermediate Similarity	NPD6011	Approved
0.7407	Intermediate Similarity	NPD5128	Approved
0.74	Intermediate Similarity	NPD6411	Approved
0.7396	Intermediate Similarity	NPD3668	Phase 3
0.7387	Intermediate Similarity	NPD4632	Approved
0.7364	Intermediate Similarity	NPD5215	Approved
0.7364	Intermediate Similarity	NPD5216	Approved
0.7364	Intermediate Similarity	NPD5217	Approved
0.7353	Intermediate Similarity	NPD5695	Phase 3
0.734	Intermediate Similarity	NPD4695	Discontinued
0.7327	Intermediate Similarity	NPD6399	Phase 3
0.7312	Intermediate Similarity	NPD3617	Approved
0.7292	Intermediate Similarity	NPD4788	Approved
0.7283	Intermediate Similarity	NPD6933	Approved
0.7273	Intermediate Similarity	NPD5135	Approved
0.7273	Intermediate Similarity	NPD5169	Approved
0.7273	Intermediate Similarity	NPD5737	Approved
0.7273	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD5134	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD6672	Approved
0.7273	Intermediate Similarity	NPD6903	Approved
0.7255	Intermediate Similarity	NPD7748	Approved
0.7253	Intermediate Similarity	NPD4058	Approved
0.7248	Intermediate Similarity	NPD5168	Approved
0.7234	Intermediate Similarity	NPD4195	Approved
0.7207	Intermediate Similarity	NPD5127	Approved
0.7207	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD6101	Approved
0.72	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7193	Intermediate Similarity	NPD7115	Discovery
0.7155	Intermediate Similarity	NPD6319	Approved
0.7155	Intermediate Similarity	NPD6054	Approved
0.7129	Intermediate Similarity	NPD4096	Approved
0.7103	Intermediate Similarity	NPD5091	Approved
0.71	Intermediate Similarity	NPD4518	Approved
0.7069	Intermediate Similarity	NPD7100	Approved
0.7069	Intermediate Similarity	NPD7101	Approved
0.7065	Intermediate Similarity	NPD6926	Approved
0.7065	Intermediate Similarity	NPD6924	Approved
0.7065	Intermediate Similarity	NPD5733	Approved
0.7065	Intermediate Similarity	NPD4687	Approved
0.7059	Intermediate Similarity	NPD5694	Approved
0.7059	Intermediate Similarity	NPD6050	Approved
0.7048	Intermediate Similarity	NPD7902	Approved
0.7043	Intermediate Similarity	NPD6009	Approved
0.7034	Intermediate Similarity	NPD6370	Approved
0.703	Intermediate Similarity	NPD6673	Approved
0.703	Intermediate Similarity	NPD6904	Approved
0.703	Intermediate Similarity	NPD6080	Approved
0.7018	Intermediate Similarity	NPD5167	Approved
0.7009	Intermediate Similarity	NPD6059	Approved
0.7	Intermediate Similarity	NPD4137	Phase 3
0.7	Intermediate Similarity	NPD3573	Approved
0.699	Remote Similarity	NPD5133	Approved
0.6989	Remote Similarity	NPD6942	Approved
0.6989	Remote Similarity	NPD7339	Approved
0.6983	Remote Similarity	NPD6335	Approved
0.6979	Remote Similarity	NPD7525	Registered
0.6979	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6961	Remote Similarity	NPD5692	Phase 3
0.6961	Remote Similarity	NPD5207	Approved
0.6957	Remote Similarity	NPD6868	Approved
0.6957	Remote Similarity	NPD6274	Approved
0.6952	Remote Similarity	NPD7614	Phase 1
0.6949	Remote Similarity	NPD6015	Approved
0.6949	Remote Similarity	NPD6016	Approved
0.6923	Remote Similarity	NPD4691	Approved
0.6923	Remote Similarity	NPD4747	Approved
0.6923	Remote Similarity	NPD4522	Approved
0.6917	Remote Similarity	NPD7492	Approved
0.6915	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD6317	Approved
0.6891	Remote Similarity	NPD5988	Approved
0.686	Remote Similarity	NPD6616	Approved
0.6857	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6854	Remote Similarity	NPD7331	Phase 2
0.6848	Remote Similarity	NPD5276	Approved
0.6842	Remote Similarity	NPD6932	Approved
0.6838	Remote Similarity	NPD6313	Approved
0.6838	Remote Similarity	NPD6314	Approved
0.6833	Remote Similarity	NPD7604	Phase 2
0.6832	Remote Similarity	NPD7524	Approved
0.6827	Remote Similarity	NPD5779	Approved
0.6827	Remote Similarity	NPD5778	Approved
0.6822	Remote Similarity	NPD7638	Approved
0.6807	Remote Similarity	NPD5983	Phase 2
0.6807	Remote Similarity	NPD6908	Approved
0.6807	Remote Similarity	NPD6909	Approved
0.6804	Remote Similarity	NPD5368	Approved
0.6804	Remote Similarity	NPD7509	Discontinued
0.6804	Remote Similarity	NPD6930	Phase 2
0.6804	Remote Similarity	NPD7332	Phase 2
0.6804	Remote Similarity	NPD6931	Approved
0.6803	Remote Similarity	NPD7078	Approved
0.68	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.68	Remote Similarity	NPD1696	Phase 3
0.6786	Remote Similarity	NPD6686	Approved
0.6771	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6768	Remote Similarity	NPD6695	Phase 3
0.6765	Remote Similarity	NPD5208	Approved
0.6762	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6762	Remote Similarity	NPD7900	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