NPASS Compound

Structure

NPC472753 OpenBabel07101719252D 33 34 0 0 1 0 0 0 0 0999 V2000 -1.5280 4.0737 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4283 4.4895 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2914 -1.7660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2914 1.7660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0131 -2.1920 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1471 -1.6920 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1437 1.4909 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8589 3.3305 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1266 -1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5388 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5574 -1.3688 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5388 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7884 2.7953 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9587 0.5598 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1192 3.5385 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6223 -1.0229 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.6223 1.0229 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.0777 -0.0000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 0.5878 -0.8090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7665 3.0032 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9587 -0.5598 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5574 1.3688 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1266 1.3090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.0131 1.1920 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.0131 -1.1920 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5878 0.8090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.0777 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.0755 3.9543 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.8722 -0.9666 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4529 2.3634 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.5131 2.0580 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.4356 2.2601 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 15 1 0 0 0 0 5 25 1 0 0 0 0 6 25 1 0 0 0 0 8 15 1 0 0 0 0 9 11 2 0 0 0 0 9 16 1 0 0 0 0 10 12 1 0 0 0 0 11 25 1 0 0 0 0 12 26 1 0 0 0 0 13 15 2 0 0 0 0 13 20 1 0 0 0 0 14 17 1 0 0 0 0 14 18 1 0 0 0 0 16 3 1 1 0 0 0 16 21 1 0 0 0 0 17 4 1 6 0 0 0 17 23 1 0 0 0 0 18 21 1 0 0 0 0 18 27 1 0 0 0 0 19 10 1 6 0 0 0 19 25 1 0 0 0 0 19 33 1 0 0 0 0 20 28 2 0 0 0 0 20 32 1 0 0 0 0 21 29 2 0 0 0 0 22 23 1 0 0 0 0 22 24 1 0 0 0 0 22 30 2 0 0 0 0 23 32 1 6 0 0 0 24 26 1 6 0 0 0 24 31 1 0 0 0 0 26 7 1 6 0 0 0 26 33 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	464.28
Volume:	489.488
LogP:	3.881
LogD:	1.545
LogS:	-3.614
# Rotatable Bonds:	4
TPSA:	106.97
# H-Bond Aceptor:	7
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.385
Synthetic Accessibility Score:	6.142
Fsp3:	0.769
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.759
MDCK Permeability:	2.051237788691651e-05
Pgp-inhibitor:	0.992
Pgp-substrate:	0.005
Human Intestinal Absorption (HIA):	0.146
20% Bioavailability (F20%):	0.01
30% Bioavailability (F30%):	0.144

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.114
Plasma Protein Binding (PPB):	93.5190200805664%
Volume Distribution (VD):	1.131
Pgp-substrate:	5.4434285163879395%

ADMET: Metabolism

CYP1A2-inhibitor:	0.007
CYP1A2-substrate:	0.178
CYP2C19-inhibitor:	0.047
CYP2C19-substrate:	0.883
CYP2C9-inhibitor:	0.064
CYP2C9-substrate:	0.11
CYP2D6-inhibitor:	0.004
CYP2D6-substrate:	0.138
CYP3A4-inhibitor:	0.568
CYP3A4-substrate:	0.565

ADMET: Excretion

Clearance (CL):	9.941
Half-life (T1/2):	0.385

ADMET: Toxicity

hERG Blockers:	0.009
Human Hepatotoxicity (H-HT):	0.899
Drug-inuced Liver Injury (DILI):	0.894
AMES Toxicity:	0.043
Rat Oral Acute Toxicity:	0.856
Maximum Recommended Daily Dose:	0.04
Skin Sensitization:	0.188
Carcinogencity:	0.097
Eye Corrosion:	0.005
Eye Irritation:	0.031
Respiratory Toxicity:	0.204

Download Data

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

Natural Product: NPC472753

Natural Product ID:	NPC472753
*Common Name:**	QYBXOOVCAISOJS-IBESDMMZSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	QYBXOOVCAISOJS-IBESDMMZSA-N
Standard InCHI:	InChI=1S/C26H40O7/c1-8-15(2)13-20(28)32-23-17(4)14-18(27)21(29)16(3)9-11-25(5,6)19-10-12-26(7,33-19)24(31)22(23)30/h9,11,13,16-19,23-24,27,31H,8,10,12,14H2,1-7H3/b11-9+,15-13+/t16-,17+,18?,19-,23+,24+,26+/m0/s1
SMILES:	CCC(=CC(=O)OC1C(CC(C(=O)C(C=CC(C2CCC(O2)(C(C1=O)O)C)(C)C)C)O)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3582000
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0003909] Fatty Acyls [CHEMONTID:0000324] Fatty acid esters

*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
NPO33329	stillingia lineata	Species	Euphorbiaceae	Eukaryota	Leaves	Langevin, La Reunion, France	2009-Nov	PMID[25946116]

☑ 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
EC50	1
Others	5

Activity Type	# Activity
Cell Line	4
NON-MOLECULAR	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT393	Cell Line	HCT-116	Homo sapiens	Inhibition	<	40.0	%	PMID[541672]
NPT83	Cell Line	MCF7	Homo sapiens	Inhibition	<	40.0	%	PMID[541672]
NPT306	Cell Line	PC-3	Homo sapiens	Inhibition	<	40.0	%	PMID[541672]
NPT189	Cell Line	Vero	Chlorocebus aethiops	CC50	>	215000.0	nM	PMID[541672]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	EC50	=	168000.0	nM	PMID[541672]
NPT2	Others	Unspecified		Ratio CC50/EC50	>	1.3	n.a.	PMID[541672]

☑ 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 NPC472753 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	216
0.1-0.2	1228
0.2-0.3	4371
0.3-0.4	7860
0.4-0.5	14002
0.5-0.6	7953
0.6-0.7	5139
0.7-0.8	1721
0.8-0.85	167
0.85-0.9	33
0.9-0.95	4
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9894	High Similarity	NPC472754
0.9583	High Similarity	NPC472755
0.9485	High Similarity	NPC472756
0.9381	High Similarity	NPC472747
0.9381	High Similarity	NPC472750
0.9286	High Similarity	NPC472748
0.9192	High Similarity	NPC472749
0.9192	High Similarity	NPC472751
0.899	High Similarity	NPC475871
0.899	High Similarity	NPC475945
0.8889	High Similarity	NPC474747
0.8889	High Similarity	NPC149371
0.8788	High Similarity	NPC133907
0.8788	High Similarity	NPC474742
0.8788	High Similarity	NPC46998
0.8788	High Similarity	NPC110443
0.8788	High Similarity	NPC128733
0.8788	High Similarity	NPC47880
0.8788	High Similarity	NPC185141
0.8713	High Similarity	NPC474741
0.8713	High Similarity	NPC203659
0.8614	High Similarity	NPC110989
0.8614	High Similarity	NPC4620
0.86	High Similarity	NPC474339
0.86	High Similarity	NPC164598
0.86	High Similarity	NPC476270
0.86	High Similarity	NPC201718
0.8586	High Similarity	NPC471144
0.8558	High Similarity	NPC38154
0.8557	High Similarity	NPC121825
0.8544	High Similarity	NPC474421
0.8544	High Similarity	NPC326994
0.8544	High Similarity	NPC477513
0.8544	High Similarity	NPC194620
0.8544	High Similarity	NPC72813
0.8544	High Similarity	NPC324327
0.8542	High Similarity	NPC30515
0.8542	High Similarity	NPC184463
0.8529	High Similarity	NPC475676
0.8529	High Similarity	NPC220964
0.8515	High Similarity	NPC225353
0.8515	High Similarity	NPC320019
0.8515	High Similarity	NPC324017
0.8469	Intermediate Similarity	NPC36954
0.8462	Intermediate Similarity	NPC233379
0.8462	Intermediate Similarity	NPC169888
0.8462	Intermediate Similarity	NPC14862
0.8462	Intermediate Similarity	NPC55972
0.8462	Intermediate Similarity	NPC474664
0.8462	Intermediate Similarity	NPC327286
0.8454	Intermediate Similarity	NPC475912
0.8454	Intermediate Similarity	NPC469645
0.8454	Intermediate Similarity	NPC469692
0.8454	Intermediate Similarity	NPC476300
0.8447	Intermediate Similarity	NPC16313
0.8447	Intermediate Similarity	NPC9303
0.8438	Intermediate Similarity	NPC476004
0.8438	Intermediate Similarity	NPC51004
0.8438	Intermediate Similarity	NPC474761
0.8431	Intermediate Similarity	NPC475873
0.8416	Intermediate Similarity	NPC15993
0.8384	Intermediate Similarity	NPC39859
0.8384	Intermediate Similarity	NPC470883
0.8384	Intermediate Similarity	NPC158416
0.8384	Intermediate Similarity	NPC76862
0.8381	Intermediate Similarity	NPC15218
0.8367	Intermediate Similarity	NPC469632
0.835	Intermediate Similarity	NPC100487
0.8333	Intermediate Similarity	NPC471148
0.8333	Intermediate Similarity	NPC307411
0.8317	Intermediate Similarity	NPC475949
0.8317	Intermediate Similarity	NPC288876
0.8316	Intermediate Similarity	NPC179659
0.8302	Intermediate Similarity	NPC5103
0.83	Intermediate Similarity	NPC40812
0.8283	Intermediate Similarity	NPC270013
0.8283	Intermediate Similarity	NPC475900
0.8283	Intermediate Similarity	NPC14961
0.8273	Intermediate Similarity	NPC475401
0.8269	Intermediate Similarity	NPC475802
0.8265	Intermediate Similarity	NPC295204
0.8265	Intermediate Similarity	NPC288240
0.8265	Intermediate Similarity	NPC81419
0.8265	Intermediate Similarity	NPC162205
0.8265	Intermediate Similarity	NPC179746
0.8265	Intermediate Similarity	NPC212486
0.8265	Intermediate Similarity	NPC273579
0.8247	Intermediate Similarity	NPC473448
0.8241	Intermediate Similarity	NPC469496
0.8241	Intermediate Similarity	NPC469463
0.8241	Intermediate Similarity	NPC469454
0.8229	Intermediate Similarity	NPC202672
0.8224	Intermediate Similarity	NPC317107
0.8218	Intermediate Similarity	NPC187761
0.8218	Intermediate Similarity	NPC83895
0.8218	Intermediate Similarity	NPC141191
0.8218	Intermediate Similarity	NPC161855
0.8208	Intermediate Similarity	NPC475922
0.82	Intermediate Similarity	NPC476315
0.82	Intermediate Similarity	NPC473859
0.82	Intermediate Similarity	NPC476009
0.82	Intermediate Similarity	NPC473291
0.8198	Intermediate Similarity	NPC477092
0.8182	Intermediate Similarity	NPC475305
0.8182	Intermediate Similarity	NPC471145
0.8182	Intermediate Similarity	NPC81386
0.8182	Intermediate Similarity	NPC474035
0.8182	Intermediate Similarity	NPC190294
0.8182	Intermediate Similarity	NPC471146
0.8163	Intermediate Similarity	NPC208886
0.8163	Intermediate Similarity	NPC20713
0.8163	Intermediate Similarity	NPC12172
0.8155	Intermediate Similarity	NPC105725
0.8148	Intermediate Similarity	NPC317687
0.8131	Intermediate Similarity	NPC161816
0.8131	Intermediate Similarity	NPC115257
0.8125	Intermediate Similarity	NPC471738
0.8119	Intermediate Similarity	NPC17326
0.8119	Intermediate Similarity	NPC169205
0.8119	Intermediate Similarity	NPC134454
0.8119	Intermediate Similarity	NPC323421
0.8119	Intermediate Similarity	NPC328562
0.8105	Intermediate Similarity	NPC11804
0.81	Intermediate Similarity	NPC193645
0.81	Intermediate Similarity	NPC471142
0.81	Intermediate Similarity	NPC90121
0.81	Intermediate Similarity	NPC275960
0.81	Intermediate Similarity	NPC475659
0.81	Intermediate Similarity	NPC48803
0.8095	Intermediate Similarity	NPC476740
0.8095	Intermediate Similarity	NPC476738
0.8081	Intermediate Similarity	NPC475302
0.8077	Intermediate Similarity	NPC69171
0.8077	Intermediate Similarity	NPC309398
0.8077	Intermediate Similarity	NPC474165
0.8061	Intermediate Similarity	NPC473619
0.8061	Intermediate Similarity	NPC316228
0.8058	Intermediate Similarity	NPC264477
0.8058	Intermediate Similarity	NPC477511
0.8056	Intermediate Similarity	NPC304180
0.8056	Intermediate Similarity	NPC179798
0.8041	Intermediate Similarity	NPC469628
0.8041	Intermediate Similarity	NPC475906
0.8041	Intermediate Similarity	NPC471047
0.8041	Intermediate Similarity	NPC469631
0.8041	Intermediate Similarity	NPC469653
0.8041	Intermediate Similarity	NPC475902
0.8039	Intermediate Similarity	NPC54843
0.8039	Intermediate Similarity	NPC473326
0.8039	Intermediate Similarity	NPC308567
0.8039	Intermediate Similarity	NPC261377
0.8039	Intermediate Similarity	NPC255592
0.8037	Intermediate Similarity	NPC42662
0.8021	Intermediate Similarity	NPC261721
0.802	Intermediate Similarity	NPC31645
0.802	Intermediate Similarity	NPC477921
0.802	Intermediate Similarity	NPC11396
0.802	Intermediate Similarity	NPC17585
0.802	Intermediate Similarity	NPC185553
0.802	Intermediate Similarity	NPC21302
0.8019	Intermediate Similarity	NPC26617
0.8018	Intermediate Similarity	NPC476712
0.8018	Intermediate Similarity	NPC476713
0.8	Intermediate Similarity	NPC470922
0.8	Intermediate Similarity	NPC258532
0.8	Intermediate Similarity	NPC477510
0.8	Intermediate Similarity	NPC471143
0.7982	Intermediate Similarity	NPC138757
0.7982	Intermediate Similarity	NPC473877
0.7981	Intermediate Similarity	NPC183571
0.7981	Intermediate Similarity	NPC473596
0.7981	Intermediate Similarity	NPC49393
0.798	Intermediate Similarity	NPC219874
0.798	Intermediate Similarity	NPC473321
0.798	Intermediate Similarity	NPC476705
0.798	Intermediate Similarity	NPC261607
0.798	Intermediate Similarity	NPC111114
0.798	Intermediate Similarity	NPC300312
0.7963	Intermediate Similarity	NPC257240
0.7963	Intermediate Similarity	NPC477103
0.7961	Intermediate Similarity	NPC477512
0.7959	Intermediate Similarity	NPC474951
0.7959	Intermediate Similarity	NPC173926
0.7957	Intermediate Similarity	NPC472948
0.7944	Intermediate Similarity	NPC322903
0.7938	Intermediate Similarity	NPC248602
0.7938	Intermediate Similarity	NPC471739
0.7938	Intermediate Similarity	NPC197333
0.7928	Intermediate Similarity	NPC476710
0.7928	Intermediate Similarity	NPC476711
0.7925	Intermediate Similarity	NPC469852
0.7921	Intermediate Similarity	NPC474947
0.7921	Intermediate Similarity	NPC477922
0.7917	Intermediate Similarity	NPC21469
0.7917	Intermediate Similarity	NPC137033
0.7913	Intermediate Similarity	NPC105926
0.7913	Intermediate Similarity	NPC91693
0.7913	Intermediate Similarity	NPC265557
0.7913	Intermediate Similarity	NPC18945
0.7913	Intermediate Similarity	NPC67251

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 NPC472753 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	197
0.1-0.2	1759
0.2-0.3	3583
0.3-0.4	2271
0.4-0.5	840
0.5-0.6	299
0.6-0.7	181
0.7-0.8	18
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.81	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.8019	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.798	Intermediate Similarity	NPD7983	Approved
0.7963	Intermediate Similarity	NPD6371	Approved
0.7879	Intermediate Similarity	NPD46	Approved
0.7879	Intermediate Similarity	NPD6698	Approved
0.7647	Intermediate Similarity	NPD5282	Discontinued
0.7525	Intermediate Similarity	NPD7838	Discovery
0.7525	Intermediate Similarity	NPD5785	Approved
0.7411	Intermediate Similarity	NPD8413	Clinical (unspecified phase)
0.7379	Intermediate Similarity	NPD5779	Approved
0.7379	Intermediate Similarity	NPD5778	Approved
0.7358	Intermediate Similarity	NPD4225	Approved
0.735	Intermediate Similarity	NPD6319	Approved
0.7297	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD6686	Approved
0.725	Intermediate Similarity	NPD7492	Approved
0.7241	Intermediate Similarity	NPD7115	Discovery
0.7203	Intermediate Similarity	NPD6054	Approved
0.72	Intermediate Similarity	NPD1733	Clinical (unspecified phase)
0.7193	Intermediate Similarity	NPD8297	Approved
0.719	Intermediate Similarity	NPD6616	Approved
0.7143	Intermediate Similarity	NPD6881	Approved
0.7143	Intermediate Similarity	NPD6899	Approved
0.7131	Intermediate Similarity	NPD7078	Approved
0.7129	Intermediate Similarity	NPD5786	Approved
0.7117	Intermediate Similarity	NPD6675	Approved
0.7117	Intermediate Similarity	NPD7128	Approved
0.7117	Intermediate Similarity	NPD5739	Approved
0.7117	Intermediate Similarity	NPD6402	Approved
0.7115	Intermediate Similarity	NPD6411	Approved
0.7083	Intermediate Similarity	NPD6370	Approved
0.7073	Intermediate Similarity	NPD7736	Approved
0.7071	Intermediate Similarity	NPD6435	Approved
0.7059	Intermediate Similarity	NPD6059	Approved
0.7054	Intermediate Similarity	NPD5697	Approved
0.703	Intermediate Similarity	NPD5363	Approved
0.7018	Intermediate Similarity	NPD7102	Approved
0.7018	Intermediate Similarity	NPD6883	Approved
0.7018	Intermediate Similarity	NPD7290	Approved
0.7009	Intermediate Similarity	NPD7839	Suspended
0.7	Intermediate Similarity	NPD8516	Approved
0.7	Intermediate Similarity	NPD6016	Approved
0.7	Intermediate Similarity	NPD7154	Phase 3
0.7	Intermediate Similarity	NPD6015	Approved
0.7	Intermediate Similarity	NPD8515	Approved
0.7	Intermediate Similarity	NPD8517	Approved
0.7	Intermediate Similarity	NPD8513	Phase 3
0.6992	Remote Similarity	NPD8293	Discontinued
0.6991	Remote Similarity	NPD7320	Approved
0.6983	Remote Similarity	NPD4632	Approved
0.697	Remote Similarity	NPD5369	Approved
0.6957	Remote Similarity	NPD6869	Approved
0.6957	Remote Similarity	NPD8130	Phase 1
0.6957	Remote Similarity	NPD6650	Approved
0.6957	Remote Similarity	NPD6617	Approved
0.6957	Remote Similarity	NPD6649	Approved
0.6957	Remote Similarity	NPD6847	Approved
0.6944	Remote Similarity	NPD6084	Phase 2
0.6944	Remote Similarity	NPD6083	Phase 2
0.6942	Remote Similarity	NPD5988	Approved
0.693	Remote Similarity	NPD6013	Approved
0.693	Remote Similarity	NPD6014	Approved
0.693	Remote Similarity	NPD6012	Approved
0.693	Remote Similarity	NPD6372	Approved
0.693	Remote Similarity	NPD6373	Approved
0.6923	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD6101	Approved
0.6909	Remote Similarity	NPD5344	Discontinued
0.6903	Remote Similarity	NPD5701	Approved
0.69	Remote Similarity	NPD4269	Approved
0.69	Remote Similarity	NPD4270	Approved
0.6899	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD6053	Discontinued
0.6897	Remote Similarity	NPD6882	Approved
0.6885	Remote Similarity	NPD8328	Phase 3
0.6881	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.688	Remote Similarity	NPD7319	Approved
0.687	Remote Similarity	NPD4634	Approved
0.6869	Remote Similarity	NPD5368	Approved
0.6842	Remote Similarity	NPD6011	Approved
0.6837	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6807	Remote Similarity	NPD6009	Approved
0.6792	Remote Similarity	NPD7637	Suspended
0.6783	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD7507	Approved
0.6759	Remote Similarity	NPD5695	Phase 3
0.6748	Remote Similarity	NPD7642	Approved
0.6748	Remote Similarity	NPD7604	Phase 2
0.6733	Remote Similarity	NPD5209	Approved
0.6733	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.6731	Remote Similarity	NPD4250	Approved
0.6731	Remote Similarity	NPD4251	Approved
0.6727	Remote Similarity	NPD7638	Approved
0.6721	Remote Similarity	NPD5983	Phase 2
0.672	Remote Similarity	NPD8074	Phase 3
0.67	Remote Similarity	NPD4819	Approved
0.67	Remote Similarity	NPD4822	Approved
0.67	Remote Similarity	NPD4252	Approved
0.67	Remote Similarity	NPD4820	Approved
0.67	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.67	Remote Similarity	NPD4821	Approved
0.6699	Remote Similarity	NPD1694	Approved
0.6667	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD8080	Discontinued
0.6667	Remote Similarity	NPD7639	Approved
0.6667	Remote Similarity	NPD5362	Discontinued
0.6667	Remote Similarity	NPD7640	Approved
0.6667	Remote Similarity	NPD6110	Phase 1
0.6641	Remote Similarity	NPD7260	Phase 2
0.664	Remote Similarity	NPD6336	Discontinued
0.6635	Remote Similarity	NPD4249	Approved
0.6613	Remote Similarity	NPD7829	Approved
0.6613	Remote Similarity	NPD7830	Approved
0.6609	Remote Similarity	NPD6412	Phase 2
0.6604	Remote Similarity	NPD1695	Approved
0.6585	Remote Similarity	NPD6921	Approved
0.6585	Remote Similarity	NPD8444	Approved
0.6577	Remote Similarity	NPD5696	Approved
0.6569	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6557	Remote Similarity	NPD7101	Approved
0.6557	Remote Similarity	NPD7100	Approved
0.6549	Remote Similarity	NPD5211	Phase 2
0.6535	Remote Similarity	NPD6033	Approved
0.6529	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6518	Remote Similarity	NPD5285	Approved
0.6518	Remote Similarity	NPD5286	Approved
0.6518	Remote Similarity	NPD6648	Approved
0.6518	Remote Similarity	NPD4696	Approved
0.6509	Remote Similarity	NPD6672	Approved
0.6509	Remote Similarity	NPD5737	Approved
0.6508	Remote Similarity	NPD8451	Approved
0.65	Remote Similarity	NPD4268	Approved
0.65	Remote Similarity	NPD4271	Approved
0.6489	Remote Similarity	NPD8415	Approved
0.6486	Remote Similarity	NPD4755	Approved
0.6481	Remote Similarity	NPD5693	Phase 1
0.6475	Remote Similarity	NPD6335	Approved
0.6457	Remote Similarity	NPD8448	Approved
0.6452	Remote Similarity	NPD8274	Clinical (unspecified phase)
0.6446	Remote Similarity	NPD6274	Approved
0.6442	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6441	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6435	Remote Similarity	NPD5141	Approved
0.6422	Remote Similarity	NPD6399	Phase 3
0.6404	Remote Similarity	NPD5224	Approved
0.6404	Remote Similarity	NPD4633	Approved
0.6404	Remote Similarity	NPD5225	Approved
0.6404	Remote Similarity	NPD5226	Approved
0.6393	Remote Similarity	NPD6317	Approved
0.6381	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6379	Remote Similarity	NPD6008	Approved
0.6378	Remote Similarity	NPD8273	Phase 1
0.6372	Remote Similarity	NPD4700	Approved
0.6364	Remote Similarity	NPD8039	Approved
0.6348	Remote Similarity	NPD5174	Approved
0.6348	Remote Similarity	NPD5175	Approved
0.6344	Remote Similarity	NPD3197	Phase 1
0.6341	Remote Similarity	NPD6314	Approved
0.6341	Remote Similarity	NPD6313	Approved
0.6341	Remote Similarity	NPD7641	Discontinued
0.6336	Remote Similarity	NPD6845	Suspended
0.632	Remote Similarity	NPD6908	Approved
0.632	Remote Similarity	NPD6909	Approved
0.6316	Remote Similarity	NPD5223	Approved
0.6316	Remote Similarity	NPD8387	Clinical (unspecified phase)
0.6311	Remote Similarity	NPD6868	Approved
0.6308	Remote Similarity	NPD8390	Approved
0.6308	Remote Similarity	NPD8391	Approved
0.6308	Remote Similarity	NPD8392	Approved
0.6308	Remote Similarity	NPD5956	Approved
0.6299	Remote Similarity	NPD8299	Approved
0.6299	Remote Similarity	NPD8342	Approved
0.6299	Remote Similarity	NPD8340	Approved
0.6299	Remote Similarity	NPD8341	Approved
0.6296	Remote Similarity	NPD6904	Approved
0.6296	Remote Similarity	NPD4753	Phase 2
0.6296	Remote Similarity	NPD5370	Suspended
0.6296	Remote Similarity	NPD6080	Approved
0.6296	Remote Similarity	NPD6673	Approved
0.6262	Remote Similarity	NPD7524	Approved
0.625	Remote Similarity	NPD5222	Approved
0.625	Remote Similarity	NPD5221	Approved
0.625	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.625	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.625	Remote Similarity	NPD2204	Approved
0.6238	Remote Similarity	NPD4756	Discovery
0.6216	Remote Similarity	NPD7748	Approved
0.6214	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6211	Remote Similarity	NPD7331	Phase 2
0.621	Remote Similarity	NPD7328	Approved
0.621	Remote Similarity	NPD7327	Approved
0.6195	Remote Similarity	NPD5173	Approved
0.6195	Remote Similarity	NPD7902	Approved
0.619	Remote Similarity	NPD7503	Approved
0.619	Remote Similarity	NPD5331	Approved
0.619	Remote Similarity	NPD8033	Approved
0.619	Remote Similarity	NPD5332	Approved
0.619	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6186	Remote Similarity	NPD5954	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