NPASS Compound

Structure

NPC39986 OpenBabel07101719142D 36 41 0 0 1 0 0 0 0 0999 V2000 0.8454 -5.3690 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0243 -1.5951 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5124 -2.4405 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5362 -1.4643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -2.9286 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.9762 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8454 -2.4405 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2734 -0.5791 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6908 -1.9524 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9266 -1.3046 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6908 -0.9762 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6908 -3.9048 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4837 -1.9470 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -4.8810 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3816 -0.9762 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.9524 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6908 -1.9524 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5362 -3.4167 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8454 -0.4881 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8454 -3.4167 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5362 -0.4881 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8454 0.4881 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.6908 0.9762 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5362 -2.4405 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6908 -0.9762 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8454 -2.4405 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -0.9762 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8454 -0.4881 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8454 -5.3690 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3816 -3.9048 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8454 0.4881 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6908 1.9524 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.4385 -2.1500 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -3.9048 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5362 0.4881 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 14 1 0 0 0 0 2 24 1 0 0 0 0 3 24 1 0 0 0 0 4 25 1 0 0 0 0 6 27 1 0 0 0 0 7 9 1 0 0 0 0 7 16 1 0 0 0 0 8 10 2 0 0 0 0 8 15 1 0 0 0 0 9 25 1 0 0 0 0 10 33 1 0 0 0 0 11 17 1 0 0 0 0 11 19 1 0 0 0 0 12 18 1 0 0 0 0 12 20 1 0 0 0 0 13 15 2 0 0 0 0 13 33 1 0 0 0 0 14 29 2 0 0 0 0 14 34 1 0 0 0 0 15 21 1 0 0 0 0 16 26 1 1 0 0 0 16 27 1 0 0 0 0 17 24 1 0 0 0 0 17 26 1 1 0 0 0 18 24 1 0 0 0 0 18 30 1 6 0 0 0 19 27 1 6 0 0 0 19 31 1 0 0 0 0 20 26 1 6 0 0 0 20 34 1 0 0 0 0 21 25 1 1 0 0 0 21 35 1 0 0 0 0 22 23 1 0 0 0 0 22 28 1 1 0 0 0 22 36 1 0 0 0 0 23 32 2 0 0 0 0 23 35 1 0 0 0 0 25 28 1 6 0 0 0 26 5 1 1 0 0 0 27 28 1 6 0 0 0 28 36 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	502.26
Volume:	501.281
LogP:	3.579
LogD:	2.728
LogS:	-5.241
# Rotatable Bonds:	3
TPSA:	118.73
# H-Bond Aceptor:	8
# H-Bond Donor:	2
# Rings:	6
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.466
Synthetic Accessibility Score:	5.669
Fsp3:	0.786
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:	-5.295
MDCK Permeability:	3.3478903787909076e-05
Pgp-inhibitor:	0.997
Pgp-substrate:	0.987
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.225
30% Bioavailability (F30%):	0.878

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.652
Plasma Protein Binding (PPB):	72.14490509033203%
Volume Distribution (VD):	1.664
Pgp-substrate:	27.163578033447266%

ADMET: Metabolism

CYP1A2-inhibitor:	0.014
CYP1A2-substrate:	0.067
CYP2C19-inhibitor:	0.012
CYP2C19-substrate:	0.457
CYP2C9-inhibitor:	0.072
CYP2C9-substrate:	0.028
CYP2D6-inhibitor:	0.008
CYP2D6-substrate:	0.157
CYP3A4-inhibitor:	0.272
CYP3A4-substrate:	0.407

ADMET: Excretion

Clearance (CL):	7.75
Half-life (T1/2):	0.228

ADMET: Toxicity

hERG Blockers:	0.101
Human Hepatotoxicity (H-HT):	0.628
Drug-inuced Liver Injury (DILI):	0.182
AMES Toxicity:	0.084
Rat Oral Acute Toxicity:	0.957
Maximum Recommended Daily Dose:	0.975
Skin Sensitization:	0.18
Carcinogencity:	0.265
Eye Corrosion:	0.137
Eye Irritation:	0.088
Respiratory Toxicity:	0.978

Download Data

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

Natural Product: NPC39986

Natural Product ID:	NPC39986
*Common Name:**	IKVZJSUBXGBGNO-RBTADCQYSA-N
IUPAC Name:	n.a.
Synonyms:	3Alpha,7Alpha-Dideacetylkhivorin
Standard InCHIKey:	IKVZJSUBXGBGNO-RBTADCQYSA-N
Standard InCHI:	InChI=1S/C28H38O8/c1-14(29)34-20-12-18(30)24(2,3)17-11-19(31)27(6)16(26(17,20)5)7-9-25(4)21(15-8-10-33-13-15)35-23(32)22-28(25,27)36-22/h8,10,13,16-22,30-31H,7,9,11-12H2,1-6H3/t16-,17+,18-,19-,20+,21-,22-,25+,26-,27+,28-/m1/s1
SMILES:	CC(=O)O[C@H]1C[C@H](C(C)(C)[C@@H]2C[C@H]([C@]3(C)[C@H](CC[C@@]4(C)[C@@H](c5ccoc5)OC(=O)[C@@H]5[C@]34O5)[C@@]12C)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2332202
PubChem CID:	71716358
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
NPO6774	Khaya senegalensis	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12193039]
NPO6774	Khaya senegalensis	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23210623]
NPO6774	Khaya senegalensis	Species	Meliaceae	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	4

Activity Type	# Activity
Organism	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	>	50.0	ug.mL-1	PMID[543701]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	MIC	>	50.0	ug.mL-1	PMID[543701]

☑ 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 NPC39986 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	365
0.1-0.2	1462
0.2-0.3	3288
0.3-0.4	5636
0.4-0.5	10042
0.5-0.6	10414
0.6-0.7	9124
0.7-0.8	1952
0.8-0.85	251
0.85-0.9	91
0.9-0.95	55
0.95-1	17

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC134254
1.0	High Similarity	NPC302369
0.9868	High Similarity	NPC335761
0.9744	High Similarity	NPC271235
0.9675	High Similarity	NPC5079
0.9613	High Similarity	NPC234660
0.9613	High Similarity	NPC51568
0.961	High Similarity	NPC472653
0.9554	High Similarity	NPC472282
0.9551	High Similarity	NPC476857
0.9551	High Similarity	NPC476856
0.9551	High Similarity	NPC476858
0.9548	High Similarity	NPC470939
0.9542	High Similarity	NPC107646
0.9494	High Similarity	NPC471397
0.9494	High Similarity	NPC160651
0.9487	High Similarity	NPC469846
0.9484	High Similarity	NPC25255
0.9484	High Similarity	NPC475381
0.9481	High Similarity	NPC286722
0.943	High Similarity	NPC476853
0.943	High Similarity	NPC476850
0.943	High Similarity	NPC476861
0.943	High Similarity	NPC472651
0.943	High Similarity	NPC173516
0.9427	High Similarity	NPC123088
0.9427	High Similarity	NPC271657
0.9423	High Similarity	NPC117986
0.9423	High Similarity	NPC82851
0.9423	High Similarity	NPC96443
0.9423	High Similarity	NPC290400
0.9423	High Similarity	NPC193798
0.9419	High Similarity	NPC473473
0.9419	High Similarity	NPC475295
0.9416	High Similarity	NPC126723
0.9416	High Similarity	NPC209364
0.9371	High Similarity	NPC472652
0.9367	High Similarity	NPC23387
0.9363	High Similarity	NPC477405
0.9355	High Similarity	NPC249021
0.9346	High Similarity	NPC469503
0.9304	High Similarity	NPC276551
0.9304	High Similarity	NPC476860
0.9299	High Similarity	NPC18347
0.9299	High Similarity	NPC200782
0.9299	High Similarity	NPC263432
0.9299	High Similarity	NPC149896
0.9299	High Similarity	NPC69028
0.9295	High Similarity	NPC475967
0.9286	High Similarity	NPC282445
0.9245	High Similarity	NPC470875
0.9241	High Similarity	NPC469338
0.9241	High Similarity	NPC292389
0.9231	High Similarity	NPC187149
0.9231	High Similarity	NPC299038
0.9231	High Similarity	NPC45101
0.9221	High Similarity	NPC476201
0.9193	High Similarity	NPC470995
0.9187	High Similarity	NPC472774
0.9187	High Similarity	NPC472775
0.9182	High Similarity	NPC469849
0.9182	High Similarity	NPC470940
0.9177	High Similarity	NPC472771
0.9172	High Similarity	NPC237155
0.9172	High Similarity	NPC477403
0.9167	High Similarity	NPC60973
0.9136	High Similarity	NPC160818
0.9136	High Similarity	NPC169299
0.9119	High Similarity	NPC476197
0.9119	High Similarity	NPC472773
0.9114	High Similarity	NPC477402
0.9114	High Similarity	NPC305016
0.9108	High Similarity	NPC472772
0.9108	High Similarity	NPC36655
0.9108	High Similarity	NPC472283
0.9108	High Similarity	NPC261597
0.9103	High Similarity	NPC44675
0.9103	High Similarity	NPC476262
0.9103	High Similarity	NPC214541
0.9103	High Similarity	NPC469336
0.9091	High Similarity	NPC476122
0.9085	High Similarity	NPC262386
0.9074	High Similarity	NPC82602
0.9068	High Similarity	NPC473753
0.9068	High Similarity	NPC473766
0.9062	High Similarity	NPC470182
0.9057	High Similarity	NPC329938
0.9045	High Similarity	NPC263265
0.9038	High Similarity	NPC178932
0.9038	High Similarity	NPC57998
0.9032	High Similarity	NPC18135
0.9006	High Similarity	NPC93172
0.9006	High Similarity	NPC97574
0.8981	High Similarity	NPC469850
0.8957	High Similarity	NPC302392
0.8938	High Similarity	NPC207978
0.8938	High Similarity	NPC188649
0.8938	High Similarity	NPC211777
0.8931	High Similarity	NPC307383
0.8931	High Similarity	NPC474611
0.8903	High Similarity	NPC125182
0.8903	High Similarity	NPC69647
0.8896	High Similarity	NPC221809
0.8896	High Similarity	NPC255414
0.8889	High Similarity	NPC41182
0.8889	High Similarity	NPC475779
0.8882	High Similarity	NPC198047
0.8882	High Similarity	NPC88841
0.8882	High Similarity	NPC288602
0.8875	High Similarity	NPC470789
0.8868	High Similarity	NPC472778
0.8868	High Similarity	NPC472777
0.8868	High Similarity	NPC167142
0.8868	High Similarity	NPC472776
0.8861	High Similarity	NPC264943
0.8861	High Similarity	NPC35000
0.8861	High Similarity	NPC281258
0.8854	High Similarity	NPC75906
0.8854	High Similarity	NPC268905
0.8854	High Similarity	NPC44577
0.8846	High Similarity	NPC477404
0.8846	High Similarity	NPC469335
0.8846	High Similarity	NPC159927
0.8846	High Similarity	NPC196864
0.8824	High Similarity	NPC86935
0.8824	High Similarity	NPC476944
0.8812	High Similarity	NPC475226
0.8805	High Similarity	NPC469485
0.8797	High Similarity	NPC30222
0.8795	High Similarity	NPC236004
0.8788	High Similarity	NPC159232
0.8782	High Similarity	NPC472654
0.8782	High Similarity	NPC195325
0.878	High Similarity	NPC242334
0.878	High Similarity	NPC296558
0.8774	High Similarity	NPC470941
0.8773	High Similarity	NPC478178
0.8773	High Similarity	NPC121995
0.8773	High Similarity	NPC472141
0.8765	High Similarity	NPC105395
0.8765	High Similarity	NPC472139
0.8758	High Similarity	NPC191828
0.8758	High Similarity	NPC243577
0.875	High Similarity	NPC173544
0.875	High Similarity	NPC88007
0.875	High Similarity	NPC194499
0.875	High Similarity	NPC195954
0.8735	High Similarity	NPC469848
0.8734	High Similarity	NPC472672
0.8727	High Similarity	NPC472659
0.8726	High Similarity	NPC46551
0.872	High Similarity	NPC100333
0.8712	High Similarity	NPC146991
0.871	High Similarity	NPC262198
0.8704	High Similarity	NPC470792
0.8704	High Similarity	NPC68848
0.8704	High Similarity	NPC18986
0.8698	High Similarity	NPC470938
0.8696	High Similarity	NPC262872
0.8696	High Similarity	NPC473368
0.8693	High Similarity	NPC121158
0.869	High Similarity	NPC478177
0.8688	High Similarity	NPC41880
0.8683	High Similarity	NPC94763
0.8683	High Similarity	NPC471437
0.8679	High Similarity	NPC253201
0.8679	High Similarity	NPC302054
0.8679	High Similarity	NPC114880
0.8667	High Similarity	NPC327922
0.8655	High Similarity	NPC242068
0.8655	High Similarity	NPC247563
0.8654	High Similarity	NPC250228
0.865	High Similarity	NPC224394
0.865	High Similarity	NPC663
0.865	High Similarity	NPC419
0.865	High Similarity	NPC165218
0.8645	High Similarity	NPC5676
0.8625	High Similarity	NPC75310
0.8616	High Similarity	NPC147168
0.8608	High Similarity	NPC212257
0.8606	High Similarity	NPC472764
0.8606	High Similarity	NPC270312
0.8606	High Similarity	NPC478179
0.859	High Similarity	NPC346
0.8589	High Similarity	NPC472668
0.8589	High Similarity	NPC79571
0.8589	High Similarity	NPC472767
0.8589	High Similarity	NPC197596
0.8581	High Similarity	NPC251865
0.8581	High Similarity	NPC137295
0.8571	High Similarity	NPC20578
0.8571	High Similarity	NPC62103
0.8563	High Similarity	NPC285227
0.8563	High Similarity	NPC475237
0.8563	High Similarity	NPC475641
0.8562	High Similarity	NPC98206
0.8562	High Similarity	NPC67003
0.8562	High Similarity	NPC34421
0.8562	High Similarity	NPC237259
0.8554	High Similarity	NPC472765

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 NPC39986 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	305
0.1-0.2	1040
0.2-0.3	2205
0.3-0.4	2636
0.4-0.5	1849
0.5-0.6	827
0.6-0.7	255
0.7-0.8	31
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
0.8625	High Similarity	NPD5760	Phase 2
0.8625	High Similarity	NPD5761	Phase 2
0.8382	Intermediate Similarity	NPD8434	Phase 2
0.7976	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7784	Intermediate Similarity	NPD6765	Approved
0.7784	Intermediate Similarity	NPD6764	Approved
0.7738	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7706	Intermediate Similarity	NPD7075	Discontinued
0.7611	Intermediate Similarity	NPD6785	Approved
0.7611	Intermediate Similarity	NPD6784	Approved
0.7596	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.756	Intermediate Similarity	NPD6599	Discontinued
0.7529	Intermediate Similarity	NPD7819	Suspended
0.7486	Intermediate Similarity	NPD6559	Discontinued
0.7471	Intermediate Similarity	NPD6801	Discontinued
0.7439	Intermediate Similarity	NPD4628	Phase 3
0.7418	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7416	Intermediate Similarity	NPD5844	Phase 1
0.7399	Intermediate Similarity	NPD3749	Approved
0.7384	Intermediate Similarity	NPD5402	Approved
0.7365	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.736	Intermediate Similarity	NPD3751	Discontinued
0.7341	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.733	Intermediate Similarity	NPD3787	Discontinued
0.7318	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7314	Intermediate Similarity	NPD5494	Approved
0.731	Intermediate Similarity	NPD7411	Suspended
0.7305	Intermediate Similarity	NPD6799	Approved
0.7286	Intermediate Similarity	NPD8404	Phase 2
0.7283	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7283	Intermediate Similarity	NPD3817	Phase 2
0.7278	Intermediate Similarity	NPD5403	Approved
0.7273	Intermediate Similarity	NPD8127	Discontinued
0.7263	Intermediate Similarity	NPD7799	Discontinued
0.7262	Intermediate Similarity	NPD5401	Approved
0.7257	Intermediate Similarity	NPD919	Approved
0.7251	Intermediate Similarity	NPD4380	Phase 2
0.7247	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7247	Intermediate Similarity	NPD6166	Phase 2
0.7247	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7246	Intermediate Similarity	NPD7236	Approved
0.7219	Intermediate Similarity	NPD6273	Approved
0.7213	Intermediate Similarity	NPD8312	Approved
0.7213	Intermediate Similarity	NPD8313	Approved
0.7207	Intermediate Similarity	NPD7473	Discontinued
0.7202	Intermediate Similarity	NPD7435	Discontinued
0.72	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7189	Intermediate Similarity	NPD8150	Discontinued
0.7176	Intermediate Similarity	NPD920	Approved
0.7158	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD3882	Suspended
0.7143	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD6232	Discontinued
0.7135	Intermediate Similarity	NPD7239	Suspended
0.7126	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7104	Intermediate Similarity	NPD7251	Discontinued
0.7093	Intermediate Similarity	NPD3226	Approved
0.7093	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7079	Intermediate Similarity	NPD1247	Approved
0.7079	Intermediate Similarity	NPD6959	Discontinued
0.7072	Intermediate Similarity	NPD3818	Discontinued
0.7069	Intermediate Similarity	NPD37	Approved
0.7065	Intermediate Similarity	NPD7808	Phase 3
0.7059	Intermediate Similarity	NPD2532	Approved
0.7059	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD2534	Approved
0.7059	Intermediate Similarity	NPD2533	Approved
0.7059	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7056	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7049	Intermediate Similarity	NPD6797	Phase 2
0.7048	Intermediate Similarity	NPD1471	Phase 3
0.7048	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7045	Intermediate Similarity	NPD4967	Phase 2
0.7045	Intermediate Similarity	NPD4965	Approved
0.7045	Intermediate Similarity	NPD7768	Phase 2
0.7045	Intermediate Similarity	NPD4966	Approved
0.7029	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7011	Intermediate Similarity	NPD7685	Pre-registration
0.7	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.6995	Remote Similarity	NPD7074	Phase 3
0.6994	Remote Similarity	NPD7458	Discontinued
0.6989	Remote Similarity	NPD8407	Phase 2
0.6985	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6985	Remote Similarity	NPD7874	Approved
0.6978	Remote Similarity	NPD7228	Approved
0.6971	Remote Similarity	NPD1934	Approved
0.6964	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD6782	Approved
0.6959	Remote Similarity	NPD6780	Approved
0.6959	Remote Similarity	NPD6781	Approved
0.6959	Remote Similarity	NPD6777	Approved
0.6959	Remote Similarity	NPD6778	Approved
0.6959	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD6779	Approved
0.6959	Remote Similarity	NPD6776	Approved
0.6951	Remote Similarity	NPD6355	Discontinued
0.6946	Remote Similarity	NPD2346	Discontinued
0.6941	Remote Similarity	NPD643	Clinical (unspecified phase)
0.694	Remote Similarity	NPD7054	Approved
0.6939	Remote Similarity	NPD7697	Approved
0.6939	Remote Similarity	NPD7698	Approved
0.6939	Remote Similarity	NPD7696	Phase 3
0.6919	Remote Similarity	NPD8368	Discontinued
0.6906	Remote Similarity	NPD3926	Phase 2
0.6905	Remote Similarity	NPD1549	Phase 2
0.6904	Remote Similarity	NPD7870	Phase 2
0.6904	Remote Similarity	NPD7871	Phase 2
0.6904	Remote Similarity	NPD8320	Phase 1
0.6904	Remote Similarity	NPD8319	Approved
0.6902	Remote Similarity	NPD7472	Approved
0.6889	Remote Similarity	NPD7199	Phase 2
0.6886	Remote Similarity	NPD1551	Phase 2
0.6886	Remote Similarity	NPD6100	Approved
0.6886	Remote Similarity	NPD2796	Approved
0.6886	Remote Similarity	NPD6099	Approved
0.6882	Remote Similarity	NPD6190	Approved
0.6872	Remote Similarity	NPD6234	Discontinued
0.6867	Remote Similarity	NPD7097	Phase 1
0.6851	Remote Similarity	NPD7229	Phase 3
0.6845	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6845	Remote Similarity	NPD5762	Approved
0.6845	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6845	Remote Similarity	NPD5763	Approved
0.6842	Remote Similarity	NPD8435	Approved
0.6836	Remote Similarity	NPD1465	Phase 2
0.6836	Remote Similarity	NPD8455	Phase 2
0.6828	Remote Similarity	NPD7240	Approved
0.6826	Remote Similarity	NPD7033	Discontinued
0.6826	Remote Similarity	NPD2799	Discontinued
0.6824	Remote Similarity	NPD3750	Approved
0.6821	Remote Similarity	NPD8285	Discontinued
0.6812	Remote Similarity	NPD7907	Approved
0.681	Remote Similarity	NPD7095	Approved
0.6805	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6804	Remote Similarity	NPD8090	Clinical (unspecified phase)
0.68	Remote Similarity	NPD7701	Phase 2
0.6796	Remote Similarity	NPD4111	Phase 1
0.6788	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6782	Remote Similarity	NPD7801	Approved
0.6782	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6768	Remote Similarity	NPD6798	Discontinued
0.6768	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6768	Remote Similarity	NPD7497	Discontinued
0.6765	Remote Similarity	NPD1243	Approved
0.6765	Remote Similarity	NPD2800	Approved
0.676	Remote Similarity	NPD7057	Phase 3
0.676	Remote Similarity	NPD7058	Phase 2
0.6754	Remote Similarity	NPD8361	Approved
0.6754	Remote Similarity	NPD8360	Approved
0.6754	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6748	Remote Similarity	NPD6832	Phase 2
0.6746	Remote Similarity	NPD5619	Clinical (unspecified phase)
0.6742	Remote Similarity	NPD2801	Approved
0.6737	Remote Similarity	NPD8424	Clinical (unspecified phase)
0.6727	Remote Similarity	NPD6233	Phase 2
0.6726	Remote Similarity	NPD3748	Approved
0.6725	Remote Similarity	NPD7003	Approved
0.6715	Remote Similarity	NPD4665	Approved
0.6703	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6701	Remote Similarity	NPD6534	Approved
0.6701	Remote Similarity	NPD4107	Approved
0.6701	Remote Similarity	NPD4580	Approved
0.6701	Remote Similarity	NPD6535	Approved
0.67	Remote Similarity	NPD7783	Phase 2
0.67	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6686	Remote Similarity	NPD2935	Discontinued
0.6684	Remote Similarity	NPD7700	Phase 2
0.6684	Remote Similarity	NPD7699	Phase 2
0.6667	Remote Similarity	NPD3764	Approved
0.6667	Remote Similarity	NPD8470	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5711	Approved
0.6667	Remote Similarity	NPD2313	Discontinued
0.6667	Remote Similarity	NPD5710	Approved
0.6651	Remote Similarity	NPD8155	Clinical (unspecified phase)
0.6647	Remote Similarity	NPD2344	Approved
0.6633	Remote Similarity	NPD2973	Approved
0.6633	Remote Similarity	NPD6823	Phase 2
0.6633	Remote Similarity	NPD2975	Approved
0.6633	Remote Similarity	NPD8485	Approved
0.6633	Remote Similarity	NPD2974	Approved
0.6633	Remote Similarity	NPD3057	Approved
0.6629	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.6629	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6629	Remote Similarity	NPD1512	Approved
0.6627	Remote Similarity	NPD1510	Phase 2
0.6609	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6601	Remote Similarity	NPD8151	Discontinued
0.6595	Remote Similarity	NPD7784	Clinical (unspecified phase)
0.659	Remote Similarity	NPD3887	Approved
0.6587	Remote Similarity	NPD4140	Approved
0.6584	Remote Similarity	NPD1608	Approved
0.6583	Remote Similarity	NPD4482	Phase 3
0.658	Remote Similarity	NPD4287	Approved
0.6567	Remote Similarity	NPD4582	Approved
0.6567	Remote Similarity	NPD4583	Approved
0.655	Remote Similarity	NPD2972	Approved
0.655	Remote Similarity	NPD6004	Phase 3
0.655	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.655	Remote Similarity	NPD6002	Phase 3
0.655	Remote Similarity	NPD3533	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