NPASS Compound

Structure

NPC107646 OpenBabel07101718292D 35 40 0 0 1 0 0 0 0 0999 V2000 -1.6898 1.9512 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0225 -1.5941 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5103 -2.4390 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -2.9268 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5347 -1.4634 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 0.9756 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8449 -2.4390 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6898 -3.9024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2709 -0.5788 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8449 -3.4146 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6898 -1.9512 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9237 -1.3038 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6898 -0.9756 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4816 -1.9459 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6898 0.9756 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3796 -0.9756 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.9512 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.6898 -1.9512 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5347 -3.4146 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8449 -0.4878 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5347 -0.4878 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8449 0.4878 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6898 0.9756 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5347 -2.4390 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8449 -2.4390 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6898 -0.9756 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 -0.9756 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8449 -0.4878 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5347 0.4878 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3796 -3.9024 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6898 1.9512 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.4359 -2.1487 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8449 0.4878 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5347 0.4878 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 15 1 0 0 0 0 2 24 1 0 0 0 0 3 24 1 0 0 0 0 5 26 1 0 0 0 0 6 27 1 0 0 0 0 7 11 1 0 0 0 0 7 17 1 0 0 0 0 8 10 1 0 0 0 0 8 19 1 0 0 0 0 9 12 2 0 0 0 0 9 16 1 0 0 0 0 10 25 1 0 0 0 0 11 26 1 0 0 0 0 12 32 1 0 0 0 0 13 18 1 0 0 0 0 13 20 1 0 0 0 0 14 16 2 0 0 0 0 14 32 1 0 0 0 0 15 29 2 0 0 0 0 15 33 1 0 0 0 0 16 21 1 0 0 0 0 17 25 1 6 0 0 0 17 27 1 0 0 0 0 18 24 1 0 0 0 0 18 25 1 6 0 0 0 19 24 1 0 0 0 0 19 30 2 0 0 0 0 20 27 1 1 0 0 0 20 33 1 0 0 0 0 21 26 1 1 0 0 0 21 34 1 0 0 0 0 22 23 1 0 0 0 0 22 28 1 1 0 0 0 22 35 1 0 0 0 0 23 31 2 0 0 0 0 23 34 1 0 0 0 0 25 4 1 6 0 0 0 26 28 1 1 0 0 0 27 28 1 1 0 0 0 28 35 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	484.25
Volume:	489.855
LogP:	3.863
LogD:	3.364
LogS:	-4.856
# Rotatable Bonds:	3
TPSA:	95.34
# H-Bond Aceptor:	7
# H-Bond Donor:	0
# Rings:	6
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.44
Synthetic Accessibility Score:	5.449
Fsp3:	0.75
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:	-5.35
MDCK Permeability:	1.634308682696428e-05
Pgp-inhibitor:	0.993
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.822
30% Bioavailability (F30%):	0.991

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.366
Plasma Protein Binding (PPB):	84.91431427001953%
Volume Distribution (VD):	1.717
Pgp-substrate:	12.57524299621582%

ADMET: Metabolism

CYP1A2-inhibitor:	0.043
CYP1A2-substrate:	0.211
CYP2C19-inhibitor:	0.286
CYP2C19-substrate:	0.753
CYP2C9-inhibitor:	0.676
CYP2C9-substrate:	0.055
CYP2D6-inhibitor:	0.021
CYP2D6-substrate:	0.245
CYP3A4-inhibitor:	0.596
CYP3A4-substrate:	0.522

ADMET: Excretion

Clearance (CL):	5.889
Half-life (T1/2):	0.613

ADMET: Toxicity

hERG Blockers:	0.007
Human Hepatotoxicity (H-HT):	0.485
Drug-inuced Liver Injury (DILI):	0.397
AMES Toxicity:	0.041
Rat Oral Acute Toxicity:	0.94
Maximum Recommended Daily Dose:	0.756
Skin Sensitization:	0.148
Carcinogencity:	0.155
Eye Corrosion:	0.12
Eye Irritation:	0.492
Respiratory Toxicity:	0.961

Download Data

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

Natural Product: NPC107646

Natural Product ID:	NPC107646
*Common Name:**	Dihydrogedunin
IUPAC Name:	n.a.
Synonyms:	1,2-Dihydrogedunin
Standard InCHIKey:	ROWFSYNHZPRCKO-BHAPSIHVSA-N
Standard InCHI:	InChI=1S/C28H36O7/c1-15(29)33-20-13-18-24(2,3)19(30)8-10-25(18,4)17-7-11-26(5)21(16-9-12-32-14-16)34-23(31)22-28(26,35-22)27(17,20)6/h9,12,14,17-18,20-22H,7-8,10-11,13H2,1-6H3/t17-,18+,20-,21+,22-,25-,26+,27+,28-/m1/s1
SMILES:	CC(=O)O[C@@H]1C[C@H]2C(C)(C)C(=O)CC[C@@]2([C@@H]2[C@]1(C)[C@@]13O[C@@H]1C(=O)O[C@H]([C@@]3(CC2)C)c1ccoc1)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL462902
PubChem CID:	21596330
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids [CHEMONTID:0002380] Limonoids

*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
NPO20413	Meliaceae spp.	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9134742]
NPO20413	Meliaceae spp.	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]

☑ 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	5

Activity Type	# Activity
Cell Line	1
Individual Protein	2
Organism	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	Activity	=	71.0	%	PMID[454625]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	>	10.0	ug.mL-1	PMID[454625]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	0.84	ug.mL-1	PMID[454625]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	Activity	<	0.39	%	PMID[454625]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	Activity	=	2.38	%	PMID[454625]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	2.63	ug.mL-1	PMID[454625]
NPT72	Individual Protein	Solute carrier organic anion transporter family member 1B3	Homo sapiens	Inhibition	=	62.45	%	PMID[454626]
NPT73	Individual Protein	Solute carrier organic anion transporter family member 1B1	Homo sapiens	Inhibition	=	35.54	%	PMID[454626]

☑ 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 NPC107646 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	435
0.1-0.2	1591
0.2-0.3	3459
0.3-0.4	6285
0.4-0.5	10466
0.5-0.6	10123
0.6-0.7	8758
0.7-0.8	1248
0.8-0.85	197
0.85-0.9	74
0.9-0.95	47
0.95-1	14

Similarity Score	Similarity Level	Natural Product ID
0.9865	High Similarity	NPC209364
0.98	High Similarity	NPC475381
0.9799	High Similarity	NPC286722
0.9735	High Similarity	NPC470939
0.9733	High Similarity	NPC475295
0.9733	High Similarity	NPC473473
0.9669	High Similarity	NPC335761
0.9605	High Similarity	NPC5079
0.96	High Similarity	NPC126723
0.96	High Similarity	NPC60973
0.9542	High Similarity	NPC39986
0.9542	High Similarity	NPC469846
0.9542	High Similarity	NPC302369
0.9542	High Similarity	NPC51568
0.9542	High Similarity	NPC134254
0.9542	High Similarity	NPC234660
0.9474	High Similarity	NPC237155
0.947	High Similarity	NPC263265
0.9412	High Similarity	NPC25255
0.9412	High Similarity	NPC305016
0.9412	High Similarity	NPC472653
0.9408	High Similarity	NPC472283
0.9363	High Similarity	NPC302392
0.9359	High Similarity	NPC473766
0.9359	High Similarity	NPC473753
0.9359	High Similarity	NPC472282
0.9355	High Similarity	NPC476856
0.9355	High Similarity	NPC476857
0.9355	High Similarity	NPC476858
0.9351	High Similarity	NPC193798
0.9299	High Similarity	NPC160651
0.9299	High Similarity	NPC271235
0.929	High Similarity	NPC476197
0.9276	High Similarity	NPC469850
0.9272	High Similarity	NPC476201
0.9267	High Similarity	NPC196864
0.9267	High Similarity	NPC477404
0.9236	High Similarity	NPC476853
0.9236	High Similarity	NPC476850
0.9236	High Similarity	NPC173516
0.9236	High Similarity	NPC476861
0.9231	High Similarity	NPC476860
0.9231	High Similarity	NPC123088
0.9226	High Similarity	NPC82851
0.9226	High Similarity	NPC96443
0.9226	High Similarity	NPC290400
0.9226	High Similarity	NPC117986
0.9205	High Similarity	NPC18135
0.9177	High Similarity	NPC471397
0.9172	High Similarity	NPC23387
0.9167	High Similarity	NPC469338
0.9167	High Similarity	NPC292389
0.9167	High Similarity	NPC477405
0.9156	High Similarity	NPC249021
0.915	High Similarity	NPC476262
0.9139	High Similarity	NPC469335
0.9139	High Similarity	NPC476122
0.9139	High Similarity	NPC159927
0.9122	High Similarity	NPC86935
0.9114	High Similarity	NPC472651
0.9108	High Similarity	NPC470940
0.9108	High Similarity	NPC469849
0.9108	High Similarity	NPC276551
0.9103	High Similarity	NPC18347
0.9103	High Similarity	NPC149896
0.9103	High Similarity	NPC263432
0.9103	High Similarity	NPC69028
0.9097	High Similarity	NPC477403
0.9097	High Similarity	NPC473368
0.9067	High Similarity	NPC221809
0.9057	High Similarity	NPC472652
0.9051	High Similarity	NPC470875
0.9038	High Similarity	NPC191828
0.9032	High Similarity	NPC167142
0.9032	High Similarity	NPC299038
0.9032	High Similarity	NPC187149
0.9026	High Similarity	NPC214541
0.9026	High Similarity	NPC44675
0.9013	High Similarity	NPC46551
0.9	High Similarity	NPC470995
0.9	High Similarity	NPC262198
0.8987	High Similarity	NPC271657
0.8981	High Similarity	NPC197596
0.8981	High Similarity	NPC329938
0.8974	High Similarity	NPC475967
0.8961	High Similarity	NPC282445
0.8961	High Similarity	NPC178932
0.894	High Similarity	NPC470941
0.8917	High Similarity	NPC477402
0.891	High Similarity	NPC261597
0.891	High Similarity	NPC45101
0.8903	High Similarity	NPC469336
0.8896	High Similarity	NPC469503
0.8889	High Similarity	NPC469848
0.8875	High Similarity	NPC472775
0.8875	High Similarity	NPC472774
0.8861	High Similarity	NPC200782
0.8861	High Similarity	NPC472771
0.8854	High Similarity	NPC307383
0.8844	High Similarity	NPC476943
0.8839	High Similarity	NPC30222
0.8839	High Similarity	NPC57998
0.8805	High Similarity	NPC472773
0.879	High Similarity	NPC472772
0.879	High Similarity	NPC36655
0.8782	High Similarity	NPC264943
0.8782	High Similarity	NPC35000
0.8774	High Similarity	NPC75906
0.8774	High Similarity	NPC44577
0.8766	High Similarity	NPC156189
0.8765	High Similarity	NPC82602
0.8758	High Similarity	NPC19747
0.875	High Similarity	NPC470182
0.8742	High Similarity	NPC142113
0.8742	High Similarity	NPC472668
0.8742	High Similarity	NPC188649
0.8742	High Similarity	NPC207978
0.8734	High Similarity	NPC474611
0.8726	High Similarity	NPC469485
0.8712	High Similarity	NPC160818
0.8712	High Similarity	NPC169299
0.8712	High Similarity	NPC159232
0.8704	High Similarity	NPC296558
0.8704	High Similarity	NPC327922
0.8696	High Similarity	NPC478178
0.8696	High Similarity	NPC475779
0.8693	High Similarity	NPC255414
0.8693	High Similarity	NPC71821
0.8688	High Similarity	NPC88841
0.8688	High Similarity	NPC224394
0.8688	High Similarity	NPC472669
0.8688	High Similarity	NPC663
0.8688	High Similarity	NPC288602
0.8684	High Similarity	NPC41182
0.8671	High Similarity	NPC173544
0.8667	High Similarity	NPC167340
0.8667	High Similarity	NPC262386
0.8662	High Similarity	NPC281258
0.8654	High Similarity	NPC268905
0.8649	High Similarity	NPC310830
0.8649	High Similarity	NPC310043
0.8642	High Similarity	NPC476224
0.8625	High Similarity	NPC6326
0.8625	High Similarity	NPC471167
0.8625	High Similarity	NPC471166
0.8625	High Similarity	NPC211777
0.8618	High Similarity	NPC476944
0.8616	High Similarity	NPC474932
0.8609	High Similarity	NPC121158
0.8606	High Similarity	NPC236004
0.8591	High Similarity	NPC220094
0.8581	High Similarity	NPC195325
0.8581	High Similarity	NPC470790
0.8581	High Similarity	NPC214572
0.8581	High Similarity	NPC69647
0.8581	High Similarity	NPC470791
0.8581	High Similarity	NPC471001
0.8581	High Similarity	NPC125182
0.8581	High Similarity	NPC472654
0.858	High Similarity	NPC93172
0.858	High Similarity	NPC97574
0.8571	High Similarity	NPC419
0.8571	High Similarity	NPC198047
0.8571	High Similarity	NPC471168
0.8571	High Similarity	NPC476035
0.8571	High Similarity	NPC14499
0.8571	High Similarity	NPC475039
0.8562	High Similarity	NPC287559
0.8562	High Similarity	NPC470789
0.8553	High Similarity	NPC194499
0.8553	High Similarity	NPC88007
0.8553	High Similarity	NPC243577
0.8553	High Similarity	NPC223415
0.8553	High Similarity	NPC195954
0.8528	High Similarity	NPC478179
0.8526	High Similarity	NPC212257
0.8509	High Similarity	NPC68848
0.8509	High Similarity	NPC18986
0.8506	High Similarity	NPC346
0.8506	High Similarity	NPC62799
0.8503	High Similarity	NPC478177
0.85	High Similarity	NPC262872
0.8497	Intermediate Similarity	NPC251865
0.8494	Intermediate Similarity	NPC94763
0.8491	Intermediate Similarity	NPC41880
0.8491	Intermediate Similarity	NPC204663
0.8481	Intermediate Similarity	NPC114880
0.8476	Intermediate Similarity	NPC242334
0.8471	Intermediate Similarity	NPC105395
0.8466	Intermediate Similarity	NPC472141
0.8466	Intermediate Similarity	NPC121995
0.8462	Intermediate Similarity	NPC211625
0.8457	Intermediate Similarity	NPC472139
0.8457	Intermediate Similarity	NPC165218
0.8452	Intermediate Similarity	NPC250228
0.8452	Intermediate Similarity	NPC216755
0.8447	Intermediate Similarity	NPC8389
0.8438	Intermediate Similarity	NPC472776
0.8438	Intermediate Similarity	NPC195131
0.8438	Intermediate Similarity	NPC472778

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 NPC107646 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	365
0.1-0.2	1063
0.2-0.3	2250
0.3-0.4	2676
0.4-0.5	1792
0.5-0.6	739
0.6-0.7	247
0.7-0.8	16
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
0.8428	Intermediate Similarity	NPD5761	Phase 2
0.8428	Intermediate Similarity	NPD5760	Phase 2
0.8221	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.8092	Intermediate Similarity	NPD8434	Phase 2
0.7701	Intermediate Similarity	NPD6765	Approved
0.7701	Intermediate Similarity	NPD6764	Approved
0.7651	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7576	Intermediate Similarity	NPD6599	Discontinued
0.7529	Intermediate Similarity	NPD5494	Approved
0.7528	Intermediate Similarity	NPD6784	Approved
0.7528	Intermediate Similarity	NPD6785	Approved
0.7515	Intermediate Similarity	NPD7075	Discontinued
0.7471	Intermediate Similarity	NPD919	Approved
0.7394	Intermediate Similarity	NPD920	Approved
0.7375	Intermediate Similarity	NPD1471	Phase 3
0.7337	Intermediate Similarity	NPD7819	Suspended
0.7322	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD6799	Approved
0.731	Intermediate Similarity	NPD3749	Approved
0.7283	Intermediate Similarity	NPD1247	Approved
0.7278	Intermediate Similarity	NPD6801	Discontinued
0.7273	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7239	Intermediate Similarity	NPD4628	Phase 3
0.7238	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7207	Intermediate Similarity	NPD6559	Discontinued
0.7193	Intermediate Similarity	NPD5402	Approved
0.7193	Intermediate Similarity	NPD3817	Phase 2
0.7175	Intermediate Similarity	NPD3751	Discontinued
0.7169	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD7236	Approved
0.7143	Intermediate Similarity	NPD3787	Discontinued
0.7135	Intermediate Similarity	NPD5844	Phase 1
0.7118	Intermediate Similarity	NPD7411	Suspended
0.7099	Intermediate Similarity	NPD2796	Approved
0.7093	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD5403	Approved
0.7079	Intermediate Similarity	NPD7799	Discontinued
0.7066	Intermediate Similarity	NPD5401	Approved
0.7055	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7052	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7052	Intermediate Similarity	NPD3882	Suspended
0.7039	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7035	Intermediate Similarity	NPD8404	Phase 2
0.7033	Intermediate Similarity	NPD8312	Approved
0.7033	Intermediate Similarity	NPD8313	Approved
0.7024	Intermediate Similarity	NPD6273	Approved
0.7022	Intermediate Similarity	NPD7473	Discontinued
0.7011	Intermediate Similarity	NPD8150	Discontinued
0.7006	Intermediate Similarity	NPD3926	Phase 2
0.7	Intermediate Similarity	NPD3226	Approved
0.7	Intermediate Similarity	NPD8285	Discontinued
0.7	Intermediate Similarity	NPD7458	Discontinued
0.6989	Remote Similarity	NPD8127	Discontinued
0.6983	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.697	Remote Similarity	NPD1243	Approved
0.697	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD6166	Phase 2
0.6966	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6964	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6963	Remote Similarity	NPD4107	Approved
0.6959	Remote Similarity	NPD4380	Phase 2
0.6951	Remote Similarity	NPD2346	Discontinued
0.6943	Remote Similarity	NPD7435	Discontinued
0.6941	Remote Similarity	NPD7239	Suspended
0.6936	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD3748	Approved
0.6928	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6901	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6893	Remote Similarity	NPD6959	Discontinued
0.6886	Remote Similarity	NPD3887	Approved
0.6885	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6882	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD1934	Approved
0.6872	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6868	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6864	Remote Similarity	NPD2533	Approved
0.6864	Remote Similarity	NPD2534	Approved
0.6864	Remote Similarity	NPD2532	Approved
0.6857	Remote Similarity	NPD7768	Phase 2
0.6855	Remote Similarity	NPD6832	Phase 2
0.6854	Remote Similarity	NPD6232	Discontinued
0.6852	Remote Similarity	NPD6355	Discontinued
0.6839	Remote Similarity	NPD4482	Phase 3
0.6832	Remote Similarity	NPD8032	Phase 2
0.6831	Remote Similarity	NPD7251	Discontinued
0.6829	Remote Similarity	NPD2799	Discontinued
0.6807	Remote Similarity	NPD1549	Phase 2
0.6796	Remote Similarity	NPD3818	Discontinued
0.6793	Remote Similarity	NPD7808	Phase 3
0.6788	Remote Similarity	NPD6099	Approved
0.6788	Remote Similarity	NPD6100	Approved
0.6776	Remote Similarity	NPD6797	Phase 2
0.6772	Remote Similarity	NPD1049	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6747	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6747	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6739	Remote Similarity	NPD7685	Pre-registration
0.6734	Remote Similarity	NPD7874	Approved
0.6734	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6726	Remote Similarity	NPD3750	Approved
0.6725	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.6722	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6721	Remote Similarity	NPD7074	Phase 3
0.672	Remote Similarity	NPD8407	Phase 2
0.6708	Remote Similarity	NPD7095	Approved
0.6701	Remote Similarity	NPD6777	Approved
0.6701	Remote Similarity	NPD6781	Approved
0.6701	Remote Similarity	NPD6779	Approved
0.6701	Remote Similarity	NPD6780	Approved
0.6701	Remote Similarity	NPD6778	Approved
0.6701	Remote Similarity	NPD6782	Approved
0.6701	Remote Similarity	NPD6776	Approved
0.6687	Remote Similarity	NPD1551	Phase 2
0.6686	Remote Similarity	NPD37	Approved
0.6685	Remote Similarity	NPD2403	Approved
0.6685	Remote Similarity	NPD7784	Clinical (unspecified phase)
0.6684	Remote Similarity	NPD7696	Phase 3
0.6684	Remote Similarity	NPD7697	Approved
0.6684	Remote Similarity	NPD7698	Approved
0.6667	Remote Similarity	NPD7054	Approved
0.6667	Remote Similarity	NPD2313	Discontinued
0.6667	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4966	Approved
0.6667	Remote Similarity	NPD4967	Phase 2
0.6667	Remote Similarity	NPD7097	Phase 1
0.6667	Remote Similarity	NPD6798	Discontinued
0.6667	Remote Similarity	NPD4965	Approved
0.6667	Remote Similarity	NPD7229	Phase 3
0.6667	Remote Similarity	NPD6808	Phase 2
0.6667	Remote Similarity	NPD2800	Approved
0.665	Remote Similarity	NPD7871	Phase 2
0.665	Remote Similarity	NPD8319	Approved
0.665	Remote Similarity	NPD7907	Approved
0.665	Remote Similarity	NPD7870	Phase 2
0.665	Remote Similarity	NPD8320	Phase 1
0.6649	Remote Similarity	NPD8368	Discontinued
0.6648	Remote Similarity	NPD2801	Approved
0.6647	Remote Similarity	NPD5763	Approved
0.6647	Remote Similarity	NPD2344	Approved
0.6647	Remote Similarity	NPD5762	Approved
0.6647	Remote Similarity	NPD2353	Approved
0.6647	Remote Similarity	NPD2355	Clinical (unspecified phase)
0.6646	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6646	Remote Similarity	NPD1933	Approved
0.6634	Remote Similarity	NPD4111	Phase 1
0.663	Remote Similarity	NPD7472	Approved
0.6627	Remote Similarity	NPD7003	Approved
0.6627	Remote Similarity	NPD7033	Discontinued
0.6626	Remote Similarity	NPD6233	Phase 2
0.6624	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6615	Remote Similarity	NPD4580	Approved
0.6612	Remote Similarity	NPD7228	Approved
0.661	Remote Similarity	NPD5616	Clinical (unspecified phase)
0.6607	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6603	Remote Similarity	NPD17	Approved
0.6599	Remote Similarity	NPD7497	Discontinued
0.6592	Remote Similarity	NPD6234	Discontinued
0.6587	Remote Similarity	NPD5619	Clinical (unspecified phase)
0.6587	Remote Similarity	NPD2935	Discontinued
0.6585	Remote Similarity	NPD4307	Phase 2
0.6582	Remote Similarity	NPD3972	Approved
0.6579	Remote Similarity	NPD8435	Approved
0.6578	Remote Similarity	NPD2968	Approved
0.6578	Remote Similarity	NPD2971	Approved
0.6573	Remote Similarity	NPD7058	Phase 2
0.6573	Remote Similarity	NPD7057	Phase 3
0.6564	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6564	Remote Similarity	NPD3764	Approved
0.6562	Remote Similarity	NPD3266	Approved
0.6562	Remote Similarity	NPD3267	Approved
0.6561	Remote Similarity	NPD8424	Clinical (unspecified phase)
0.6554	Remote Similarity	NPD1465	Phase 2
0.6554	Remote Similarity	NPD8455	Phase 2
0.6553	Remote Similarity	NPD4665	Approved
0.655	Remote Similarity	NPD7701	Phase 2
0.6548	Remote Similarity	NPD3057	Approved
0.6546	Remote Similarity	NPD2974	Approved
0.6546	Remote Similarity	NPD2973	Approved
0.6546	Remote Similarity	NPD8090	Clinical (unspecified phase)
0.6546	Remote Similarity	NPD2975	Approved
0.6537	Remote Similarity	NPD5980	Discovery
0.6535	Remote Similarity	NPD7801	Approved
0.6532	Remote Similarity	NPD1512	Approved
0.6527	Remote Similarity	NPD1510	Phase 2
0.6519	Remote Similarity	NPD7199	Phase 2
0.6517	Remote Similarity	NPD5353	Approved
0.6512	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6509	Remote Similarity	NPD2897	Discontinued
0.6492	Remote Similarity	NPD8361	Approved
0.6492	Remote Similarity	NPD4287	Approved
0.6492	Remote Similarity	NPD8360	Approved
0.6491	Remote Similarity	NPD6190	Approved
0.6491	Remote Similarity	NPD2354	Approved
0.6491	Remote Similarity	NPD2309	Approved
0.6488	Remote Similarity	NPD2438	Suspended
0.6485	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6484	Remote Similarity	NPD5710	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