NPASS Compound

Structure

NPC470155 OpenBabel07101718322D 30 32 0 0 1 0 0 0 0 0999 V2000 2.3651 1.0486 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6526 0.4803 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6153 -2.6591 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7168 0.7954 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8275 1.1755 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1735 -2.1491 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4581 -1.0660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2930 -0.2668 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2930 -0.9633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5275 1.5322 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2993 1.3806 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3089 -2.9442 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6899 0.0814 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.4390 -0.6151 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.1368 0.0124 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.4578 0.1674 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8027 -1.3434 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.9429 0.2152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6899 -1.3115 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0867 -0.2668 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0867 -0.9633 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.5275 2.4994 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.9023 2.1368 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5241 -3.8872 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.2426 1.1104 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.2063 -2.1491 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.6899 1.0486 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3429 1.5248 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0179 -2.2864 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 10 1 0 0 0 0 2 11 1 0 0 0 0 3 12 1 0 0 0 0 4 18 1 0 0 0 0 5 18 1 0 0 0 0 6 19 1 0 0 0 0 7 20 1 0 0 0 0 8 9 1 0 0 0 0 8 13 1 0 0 0 0 9 19 1 0 0 0 0 10 22 2 0 0 0 0 10 27 1 0 0 0 0 11 23 2 0 0 0 0 11 28 1 0 0 0 0 12 24 2 0 0 0 0 12 29 1 0 0 0 0 13 20 1 1 0 0 0 13 27 1 0 0 0 0 14 15 1 0 0 0 0 14 17 1 0 0 0 0 14 18 1 6 0 0 0 15 16 1 0 0 0 0 15 28 1 6 0 0 0 16 20 1 6 0 0 0 16 25 1 0 0 0 0 17 21 1 6 0 0 0 17 29 1 0 0 0 0 18 30 1 0 0 0 0 19 21 1 1 0 0 0 19 26 1 0 0 0 0 20 21 1 6 0 0 0 21 30 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	428.2
Volume:	417.305
LogP:	1.429
LogD:	0.799
LogS:	-3.312
# Rotatable Bonds:	6
TPSA:	128.59
# H-Bond Aceptor:	9
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.497
Synthetic Accessibility Score:	5.861
Fsp3:	0.857
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.28
MDCK Permeability:	9.023900202009827e-05
Pgp-inhibitor:	0.988
Pgp-substrate:	0.221
Human Intestinal Absorption (HIA):	0.631
20% Bioavailability (F20%):	0.409
30% Bioavailability (F30%):	0.986

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.291
Plasma Protein Binding (PPB):	26.807575225830078%
Volume Distribution (VD):	0.994
Pgp-substrate:	50.95161056518555%

ADMET: Metabolism

CYP1A2-inhibitor:	0.013
CYP1A2-substrate:	0.044
CYP2C19-inhibitor:	0.009
CYP2C19-substrate:	0.315
CYP2C9-inhibitor:	0.002
CYP2C9-substrate:	0.025
CYP2D6-inhibitor:	0.172
CYP2D6-substrate:	0.08
CYP3A4-inhibitor:	0.116
CYP3A4-substrate:	0.369

ADMET: Excretion

Clearance (CL):	2.927
Half-life (T1/2):	0.843

ADMET: Toxicity

hERG Blockers:	0.041
Human Hepatotoxicity (H-HT):	0.947
Drug-inuced Liver Injury (DILI):	0.903
AMES Toxicity:	0.027
Rat Oral Acute Toxicity:	0.534
Maximum Recommended Daily Dose:	0.029
Skin Sensitization:	0.204
Carcinogencity:	0.197
Eye Corrosion:	0.004
Eye Irritation:	0.015
Respiratory Toxicity:	0.891

Download Data

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

Natural Product: NPC470155

Natural Product ID:	NPC470155
*Common Name:**	AABFKSBKMOPMPR-HTFIHRAASA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	AABFKSBKMOPMPR-HTFIHRAASA-N
Standard InCHI:	InChI=1S/C21H32O9/c1-10(22)27-13-8-9-19(6,26)21-17(29-12(3)24)14(18(4,5)30-21)15(28-11(2)23)16(25)20(13,21)7/h13-17,25-26H,8-9H2,1-7H3/t13-,14+,15-,16-,17+,19-,20-,21-/m0/s1
SMILES:	CC(=O)OC1CCC(C23C1(C(C(C(C2OC(=O)C)C(O3)(C)C)OC(=O)C)O)C)(C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1796010
PubChem CID:	56673912
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001550] Sesquiterpenoids [CHEMONTID:0002051] Agarofurans

*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
NPO15653	Celastrus vulcanicola	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18616221]
NPO15653	Celastrus vulcanicola	Species	Celastraceae	Eukaryota	stems	Montecristo National Park, province of Santa Ana, El Salvador	2004-JUN	PMID[20873773]
NPO15653	Celastrus vulcanicola	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21419633]
NPO15653	Celastrus vulcanicola	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25695368]
NPO15653	Celastrus vulcanicola	Species	Celastraceae	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
MIC	2

Activity Type	# Activity
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT88	Organism	Mycobacterium tuberculosis	Mycobacterium tuberculosis	MIC	>	25.0	ug.mL-1	PMID[500858]
NPT790	Organism	Mycobacterium tuberculosis H37Rv	Mycobacterium tuberculosis H37Rv	MIC	>	25.0	ug.mL-1	PMID[500858]

☑ 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 NPC470155 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	372
0.1-0.2	3178
0.2-0.3	8889
0.3-0.4	13827
0.4-0.5	6257
0.5-0.6	5706
0.6-0.7	3754
0.7-0.8	637
0.8-0.85	52
0.85-0.9	17
0.9-0.95	3
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC477447
1.0	High Similarity	NPC477446
0.9868	High Similarity	NPC470156
0.9868	High Similarity	NPC470154
0.9231	High Similarity	NPC472951
0.9231	High Similarity	NPC472943
0.9146	High Similarity	NPC213658
0.9146	High Similarity	NPC45833
0.9146	High Similarity	NPC62202
0.9146	High Similarity	NPC110365
0.8974	High Similarity	NPC43463
0.8947	High Similarity	NPC470151
0.8875	High Similarity	NPC211049
0.8795	High Similarity	NPC471411
0.8795	High Similarity	NPC471410
0.8795	High Similarity	NPC215968
0.8795	High Similarity	NPC155531
0.8795	High Similarity	NPC477283
0.878	High Similarity	NPC18953
0.8765	High Similarity	NPC60018
0.8765	High Similarity	NPC202688
0.8765	High Similarity	NPC154043
0.875	High Similarity	NPC186594
0.8718	High Similarity	NPC136424
0.8675	High Similarity	NPC266651
0.8642	High Similarity	NPC116320
0.8642	High Similarity	NPC119922
0.8621	High Similarity	NPC475307
0.859	High Similarity	NPC472950
0.859	High Similarity	NPC472952
0.8588	High Similarity	NPC476435
0.8588	High Similarity	NPC476379
0.8588	High Similarity	NPC470872
0.8537	High Similarity	NPC216800
0.85	High Similarity	NPC191345
0.85	High Similarity	NPC252483
0.8471	Intermediate Similarity	NPC5943
0.8434	Intermediate Similarity	NPC241959
0.8434	Intermediate Similarity	NPC111582
0.8434	Intermediate Similarity	NPC477285
0.8391	Intermediate Similarity	NPC470114
0.8375	Intermediate Similarity	NPC476719
0.8372	Intermediate Similarity	NPC471221
0.8353	Intermediate Similarity	NPC131365
0.8313	Intermediate Similarity	NPC286719
0.8313	Intermediate Similarity	NPC477284
0.8313	Intermediate Similarity	NPC477286
0.8295	Intermediate Similarity	NPC473066
0.8293	Intermediate Similarity	NPC474714
0.8293	Intermediate Similarity	NPC186588
0.8256	Intermediate Similarity	NPC471377
0.8235	Intermediate Similarity	NPC235402
0.8235	Intermediate Similarity	NPC477445
0.8228	Intermediate Similarity	NPC472945
0.8228	Intermediate Similarity	NPC472944
0.8202	Intermediate Similarity	NPC256104
0.8202	Intermediate Similarity	NPC122083
0.8202	Intermediate Similarity	NPC182740
0.8202	Intermediate Similarity	NPC211845
0.8193	Intermediate Similarity	NPC190940
0.8193	Intermediate Similarity	NPC71541
0.8171	Intermediate Similarity	NPC477282
0.8171	Intermediate Similarity	NPC81074
0.8161	Intermediate Similarity	NPC201607
0.8161	Intermediate Similarity	NPC56777
0.8158	Intermediate Similarity	NPC476928
0.814	Intermediate Similarity	NPC246347
0.814	Intermediate Similarity	NPC228593
0.814	Intermediate Similarity	NPC268633
0.814	Intermediate Similarity	NPC279260
0.814	Intermediate Similarity	NPC235196
0.8118	Intermediate Similarity	NPC320824
0.8101	Intermediate Similarity	NPC123122
0.8095	Intermediate Similarity	NPC2096
0.8095	Intermediate Similarity	NPC208912
0.809	Intermediate Similarity	NPC219516
0.8072	Intermediate Similarity	NPC471217
0.8072	Intermediate Similarity	NPC471216
0.8072	Intermediate Similarity	NPC16449
0.8068	Intermediate Similarity	NPC477443
0.8068	Intermediate Similarity	NPC477440
0.8065	Intermediate Similarity	NPC188968
0.8065	Intermediate Similarity	NPC51579
0.8049	Intermediate Similarity	NPC272841
0.8023	Intermediate Similarity	NPC93616
0.8022	Intermediate Similarity	NPC57964
0.8022	Intermediate Similarity	NPC94582
0.8	Intermediate Similarity	NPC213737
0.8	Intermediate Similarity	NPC474253
0.8	Intermediate Similarity	NPC474346
0.8	Intermediate Similarity	NPC475820
0.8	Intermediate Similarity	NPC474284
0.8	Intermediate Similarity	NPC69953
0.7978	Intermediate Similarity	NPC477442
0.7978	Intermediate Similarity	NPC18536
0.7978	Intermediate Similarity	NPC477444
0.7978	Intermediate Similarity	NPC50443
0.7978	Intermediate Similarity	NPC477433
0.7976	Intermediate Similarity	NPC475743
0.7976	Intermediate Similarity	NPC73515
0.7957	Intermediate Similarity	NPC471374
0.7957	Intermediate Similarity	NPC209798
0.7957	Intermediate Similarity	NPC471375
0.7952	Intermediate Similarity	NPC476176
0.7952	Intermediate Similarity	NPC477287
0.7949	Intermediate Similarity	NPC470833
0.7935	Intermediate Similarity	NPC237071
0.7935	Intermediate Similarity	NPC169270
0.7935	Intermediate Similarity	NPC306797
0.7935	Intermediate Similarity	NPC203434
0.7935	Intermediate Similarity	NPC292718
0.7935	Intermediate Similarity	NPC111834
0.7935	Intermediate Similarity	NPC116683
0.7935	Intermediate Similarity	NPC238796
0.7935	Intermediate Similarity	NPC235109
0.7931	Intermediate Similarity	NPC474008
0.7931	Intermediate Similarity	NPC114378
0.7931	Intermediate Similarity	NPC107603
0.7931	Intermediate Similarity	NPC103782
0.7927	Intermediate Similarity	NPC11907
0.7927	Intermediate Similarity	NPC64081
0.7927	Intermediate Similarity	NPC307865
0.7927	Intermediate Similarity	NPC133596
0.7927	Intermediate Similarity	NPC474574
0.7912	Intermediate Similarity	NPC191915
0.7912	Intermediate Similarity	NPC151214
0.7907	Intermediate Similarity	NPC473299
0.7907	Intermediate Similarity	NPC65133
0.7907	Intermediate Similarity	NPC477434
0.7901	Intermediate Similarity	NPC158208
0.7901	Intermediate Similarity	NPC186851
0.7901	Intermediate Similarity	NPC243027
0.7901	Intermediate Similarity	NPC196136
0.7889	Intermediate Similarity	NPC216137
0.7875	Intermediate Similarity	NPC476718
0.7872	Intermediate Similarity	NPC471426
0.7872	Intermediate Similarity	NPC471428
0.7872	Intermediate Similarity	NPC471427
0.7849	Intermediate Similarity	NPC274793
0.7831	Intermediate Similarity	NPC147993
0.7831	Intermediate Similarity	NPC471045
0.7831	Intermediate Similarity	NPC177343
0.7826	Intermediate Similarity	NPC82633
0.7826	Intermediate Similarity	NPC241047
0.7816	Intermediate Similarity	NPC476715
0.7812	Intermediate Similarity	NPC61442
0.7805	Intermediate Similarity	NPC107963
0.7791	Intermediate Similarity	NPC15091
0.7791	Intermediate Similarity	NPC29342
0.7791	Intermediate Similarity	NPC2572
0.7789	Intermediate Similarity	NPC49532
0.7789	Intermediate Similarity	NPC475574
0.7778	Intermediate Similarity	NPC472146
0.7778	Intermediate Similarity	NPC470262
0.7778	Intermediate Similarity	NPC10476
0.7778	Intermediate Similarity	NPC192501
0.7778	Intermediate Similarity	NPC185529
0.7778	Intermediate Similarity	NPC228994
0.7766	Intermediate Similarity	NPC292775
0.7766	Intermediate Similarity	NPC472144
0.7763	Intermediate Similarity	NPC94897
0.7753	Intermediate Similarity	NPC128475
0.7753	Intermediate Similarity	NPC470260
0.7753	Intermediate Similarity	NPC75443
0.7742	Intermediate Similarity	NPC156377
0.7742	Intermediate Similarity	NPC163685
0.7742	Intermediate Similarity	NPC475785
0.7742	Intermediate Similarity	NPC252056
0.7742	Intermediate Similarity	NPC475765
0.7742	Intermediate Similarity	NPC296936
0.7738	Intermediate Similarity	NPC220379
0.7727	Intermediate Similarity	NPC64862
0.7727	Intermediate Similarity	NPC471240
0.7717	Intermediate Similarity	NPC477224
0.7717	Intermediate Similarity	NPC113500
0.7717	Intermediate Similarity	NPC3538
0.7711	Intermediate Similarity	NPC212453
0.7711	Intermediate Similarity	NPC302578
0.7711	Intermediate Similarity	NPC128951
0.7711	Intermediate Similarity	NPC105208
0.7711	Intermediate Similarity	NPC192046
0.7711	Intermediate Similarity	NPC477227
0.7711	Intermediate Similarity	NPC171658
0.7708	Intermediate Similarity	NPC471254
0.7692	Intermediate Similarity	NPC41838
0.7692	Intermediate Similarity	NPC91251
0.7692	Intermediate Similarity	NPC293609
0.7684	Intermediate Similarity	NPC79303
0.7683	Intermediate Similarity	NPC270306
0.7683	Intermediate Similarity	NPC91387
0.7683	Intermediate Similarity	NPC231680
0.7674	Intermediate Similarity	NPC475388
0.7674	Intermediate Similarity	NPC242771
0.7674	Intermediate Similarity	NPC121121
0.7674	Intermediate Similarity	NPC100366
0.7674	Intermediate Similarity	NPC164289
0.7674	Intermediate Similarity	NPC311642
0.7667	Intermediate Similarity	NPC20822
0.7667	Intermediate Similarity	NPC82955
0.766	Intermediate Similarity	NPC472145

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 NPC470155 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	384
0.1-0.2	3631
0.2-0.3	3391
0.3-0.4	1012
0.4-0.5	368
0.5-0.6	268
0.6-0.7	87
0.7-0.8	9
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7848	Intermediate Similarity	NPD7532	Clinical (unspecified phase)
0.7532	Intermediate Similarity	NPD371	Approved
0.7284	Intermediate Similarity	NPD4267	Clinical (unspecified phase)
0.7209	Intermediate Similarity	NPD6697	Approved
0.7209	Intermediate Similarity	NPD6118	Approved
0.7209	Intermediate Similarity	NPD6115	Approved
0.7209	Intermediate Similarity	NPD6114	Approved
0.7157	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7093	Intermediate Similarity	NPD6116	Phase 1
0.7087	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7053	Intermediate Similarity	NPD8171	Discontinued
0.6977	Remote Similarity	NPD6117	Approved
0.69	Remote Similarity	NPD1700	Approved
0.6857	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6854	Remote Similarity	NPD6928	Phase 2
0.6818	Remote Similarity	NPD7516	Approved
0.6813	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.6813	Remote Similarity	NPD3669	Approved
0.6762	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6744	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6727	Remote Similarity	NPD7327	Approved
0.6727	Remote Similarity	NPD7328	Approved
0.6699	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6571	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6569	Remote Similarity	NPD5344	Discontinued
0.6552	Remote Similarity	NPD1810	Approved
0.6552	Remote Similarity	NPD1811	Approved
0.6549	Remote Similarity	NPD6921	Approved
0.6514	Remote Similarity	NPD8133	Approved
0.6477	Remote Similarity	NPD3703	Phase 2
0.6404	Remote Similarity	NPD8378	Approved
0.6404	Remote Similarity	NPD8296	Approved
0.6404	Remote Similarity	NPD8380	Approved
0.6404	Remote Similarity	NPD8335	Approved
0.6404	Remote Similarity	NPD8379	Approved
0.6373	Remote Similarity	NPD7638	Approved
0.6373	Remote Similarity	NPD4225	Approved
0.6354	Remote Similarity	NPD7524	Approved
0.6322	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6322	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD8294	Approved
0.6316	Remote Similarity	NPD8377	Approved
0.6311	Remote Similarity	NPD7640	Approved
0.6311	Remote Similarity	NPD7639	Approved
0.6292	Remote Similarity	NPD3702	Approved
0.6279	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6279	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6263	Remote Similarity	NPD8035	Phase 2
0.6263	Remote Similarity	NPD8034	Phase 2
0.6261	Remote Similarity	NPD8033	Approved
0.6207	Remote Similarity	NPD4787	Phase 1
0.6207	Remote Similarity	NPD2687	Approved
0.6207	Remote Similarity	NPD2686	Approved
0.6207	Remote Similarity	NPD2254	Approved
0.6204	Remote Similarity	NPD6686	Approved
0.6195	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.619	Remote Similarity	NPD7632	Discontinued
0.6174	Remote Similarity	NPD6319	Approved
0.6154	Remote Similarity	NPD6648	Approved
0.6146	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6136	Remote Similarity	NPD5777	Approved
0.6129	Remote Similarity	NPD7525	Registered
0.6126	Remote Similarity	NPD8297	Approved
0.6121	Remote Similarity	NPD7503	Approved
0.6106	Remote Similarity	NPD6940	Discontinued
0.6071	Remote Similarity	NPD4632	Approved
0.6064	Remote Similarity	NPD1780	Approved
0.6064	Remote Similarity	NPD1779	Approved
0.605	Remote Similarity	NPD7507	Approved
0.6042	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6033	Remote Similarity	NPD7319	Approved
0.6023	Remote Similarity	NPD4245	Approved
0.6023	Remote Similarity	NPD4244	Approved
0.6019	Remote Similarity	NPD6675	Approved
0.6019	Remote Similarity	NPD5739	Approved
0.6019	Remote Similarity	NPD7128	Approved
0.6019	Remote Similarity	NPD6402	Approved
0.6	Remote Similarity	NPD6372	Approved
0.6	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.6	Remote Similarity	NPD6373	Approved
0.5977	Remote Similarity	NPD5360	Phase 3
0.5977	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.5966	Remote Similarity	NPD7492	Approved
0.5963	Remote Similarity	NPD6412	Phase 2
0.5955	Remote Similarity	NPD6081	Approved
0.5938	Remote Similarity	NPD6695	Phase 3
0.593	Remote Similarity	NPD4224	Phase 2
0.5922	Remote Similarity	NPD7991	Discontinued
0.5917	Remote Similarity	NPD6616	Approved
0.5909	Remote Similarity	NPD6881	Approved
0.5909	Remote Similarity	NPD6899	Approved
0.5909	Remote Similarity	NPD7320	Approved
0.5909	Remote Similarity	NPD3698	Phase 2
0.5897	Remote Similarity	NPD6059	Approved
0.5897	Remote Similarity	NPD6054	Approved
0.5893	Remote Similarity	NPD6649	Approved
0.5893	Remote Similarity	NPD6650	Approved
0.5882	Remote Similarity	NPD6399	Phase 3
0.5882	Remote Similarity	NPD8328	Phase 3
0.5882	Remote Similarity	NPD7909	Approved
0.5868	Remote Similarity	NPD7078	Approved
0.5868	Remote Similarity	NPD8293	Discontinued
0.5851	Remote Similarity	NPD7645	Phase 2
0.5849	Remote Similarity	NPD8418	Phase 2
0.5843	Remote Similarity	NPD4789	Approved
0.5842	Remote Similarity	NPD3168	Discontinued
0.5841	Remote Similarity	NPD6882	Approved
0.5825	Remote Similarity	NPD7748	Approved
0.582	Remote Similarity	NPD7736	Approved
0.5818	Remote Similarity	NPD5697	Approved
0.5818	Remote Similarity	NPD5701	Approved
0.581	Remote Similarity	NPD7902	Approved
0.5804	Remote Similarity	NPD7102	Approved
0.5804	Remote Similarity	NPD7290	Approved
0.5804	Remote Similarity	NPD6883	Approved
0.5798	Remote Similarity	NPD6370	Approved
0.5794	Remote Similarity	NPD4159	Approved
0.5784	Remote Similarity	NPD7515	Phase 2
0.5784	Remote Similarity	NPD7637	Suspended
0.5776	Remote Similarity	NPD6009	Approved
0.5776	Remote Similarity	NPD7115	Discovery
0.5752	Remote Similarity	NPD8130	Phase 1
0.5752	Remote Similarity	NPD6617	Approved
0.5752	Remote Similarity	NPD6869	Approved
0.5752	Remote Similarity	NPD6847	Approved
0.575	Remote Similarity	NPD7604	Phase 2
0.5745	Remote Similarity	NPD3671	Phase 1
0.5727	Remote Similarity	NPD6008	Approved
0.5714	Remote Similarity	NPD6015	Approved
0.5714	Remote Similarity	NPD5983	Phase 2
0.5714	Remote Similarity	NPD6014	Approved
0.5714	Remote Similarity	NPD6012	Approved
0.5714	Remote Similarity	NPD6016	Approved
0.5714	Remote Similarity	NPD6013	Approved
0.57	Remote Similarity	NPD7750	Discontinued
0.5667	Remote Similarity	NPD5988	Approved
0.566	Remote Similarity	NPD6084	Phase 2
0.566	Remote Similarity	NPD6083	Phase 2
0.5658	Remote Similarity	NPD385	Approved
0.5658	Remote Similarity	NPD384	Approved
0.5656	Remote Similarity	NPD6336	Discontinued
0.5636	Remote Similarity	NPD4056	Clinical (unspecified phase)
0.5636	Remote Similarity	NPD4057	Clinical (unspecified phase)
0.5625	Remote Similarity	NPD6011	Approved
0.5625	Remote Similarity	NPD6931	Approved
0.5625	Remote Similarity	NPD6930	Phase 2
0.5625	Remote Similarity	NPD8174	Phase 2
0.5618	Remote Similarity	NPD229	Approved
0.5614	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.5604	Remote Similarity	NPD4758	Discontinued

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data