NPASS Compound

Structure

NPC472686 OpenBabel07101719132D 41 42 0 0 1 0 0 0 0 0999 V2000 4.1616 1.9689 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5370 -4.4017 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8313 -3.3156 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5888 -5.1000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0521 -4.2552 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2350 -3.9205 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6225 -2.9562 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2403 2.8804 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4424 3.0336 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3283 1.3016 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6165 -1.9905 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9923 1.0082 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5772 -1.8211 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2436 -2.7377 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5888 -3.4103 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0766 -2.5655 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0937 -2.2367 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2663 1.4998 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9502 -1.0738 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1216 -2.3183 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0634 0.9374 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9749 -1.8289 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8706 -3.4850 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0766 -4.2552 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6504 -3.0378 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3547 2.4713 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0756 0.6745 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 1.5888 -1.7207 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.9895 -0.6198 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.9062 -0.2862 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5888 -0.1423 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2438 -0.9718 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3336 -0.9167 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9895 -1.2432 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.4351 -1.5173 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.9749 -0.0340 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.6535 -0.9132 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.0766 0.7025 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.0772 -1.6391 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2714 -1.1856 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 12 1 0 0 0 0 2 23 1 0 0 0 0 3 23 1 0 0 0 0 4 24 1 0 0 0 0 5 24 1 0 0 0 0 6 25 1 0 0 0 0 7 25 1 0 0 0 0 8 26 1 0 0 0 0 9 26 1 0 0 0 0 10 27 1 0 0 0 0 12 27 1 0 0 0 0 13 14 1 0 0 0 0 13 19 1 0 0 0 0 14 23 2 0 0 0 0 15 16 1 0 0 0 0 15 24 2 0 0 0 0 16 28 1 0 0 0 0 17 20 1 0 0 0 0 17 25 2 0 0 0 0 18 21 1 0 0 0 0 18 26 2 0 0 0 0 19 34 1 0 0 0 0 22 28 1 0 0 0 0 22 35 1 0 0 0 0 27 30 1 0 0 0 0 28 34 1 1 0 0 0 29 30 1 0 0 0 0 29 31 1 0 0 0 0 29 34 1 1 0 0 0 30 37 2 0 0 0 0 31 36 1 0 0 0 0 31 38 2 0 0 0 0 32 35 1 0 0 0 0 32 36 1 0 0 0 0 32 39 2 0 0 0 0 33 35 1 0 0 0 0 33 40 2 0 0 0 0 33 41 1 0 0 0 0 34 11 1 1 0 0 0 35 20 1 6 0 0 0 36 21 1 6 0 0 0 36 41 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	566.4
Volume:	636.958
LogP:	9.188
LogD:	5.718
LogS:	-4.213
# Rotatable Bonds:	12
TPSA:	77.51
# H-Bond Aceptor:	5
# H-Bond Donor:	0
# Rings:	2
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.134
Synthetic Accessibility Score:	6.044
Fsp3:	0.667
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	2
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.936
MDCK Permeability:	1.2472594789869618e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.023
Human Intestinal Absorption (HIA):	0.179
20% Bioavailability (F20%):	0.979
30% Bioavailability (F30%):	0.825

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.031
Plasma Protein Binding (PPB):	88.93250274658203%
Volume Distribution (VD):	3.146
Pgp-substrate:	5.446235179901123%

ADMET: Metabolism

CYP1A2-inhibitor:	0.011
CYP1A2-substrate:	0.38
CYP2C19-inhibitor:	0.364
CYP2C19-substrate:	0.931
CYP2C9-inhibitor:	0.331
CYP2C9-substrate:	0.075
CYP2D6-inhibitor:	0.013
CYP2D6-substrate:	0.014
CYP3A4-inhibitor:	0.891
CYP3A4-substrate:	0.906

ADMET: Excretion

Clearance (CL):	17.654
Half-life (T1/2):	0.017

ADMET: Toxicity

hERG Blockers:	0.002
Human Hepatotoxicity (H-HT):	0.941
Drug-inuced Liver Injury (DILI):	0.939
AMES Toxicity:	0.097
Rat Oral Acute Toxicity:	0.98
Maximum Recommended Daily Dose:	0.016
Skin Sensitization:	0.026
Carcinogencity:	0.199
Eye Corrosion:	0.012
Eye Irritation:	0.063
Respiratory Toxicity:	0.954

Download Data

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

Natural Product: NPC472686

Natural Product ID:	NPC472686
*Common Name:**	QKPKQCWTPSIKTJ-KWPZVDDNSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	QKPKQCWTPSIKTJ-KWPZVDDNSA-N
Standard InCHI:	InChI=1S/C36H54O5/c1-12-27(10)30(37)29-31(38)36(21-18-26(8)9)32(39)35(33(40)41-36,20-17-25(6)7)22-28(16-15-24(4)5)34(29,11)19-13-14-23(2)3/h14-15,17-18,27-29H,12-13,16,19-22H2,1-11H3/t27?,28-,29+,34+,35+,36-/m0/s1
SMILES:	CCC(C)C(=O)C1C(=O)C2(C(=O)C(CC(C1(C)CCC=C(C)C)CC=C(C)C)(C(=O)O2)CC=C(C)C)CC=C(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3581585
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones

*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
NPO19915	Hypericum henryi	Species	Hypericaceae	Eukaryota	aerial parts	Yunnan, China	n.a.	PMID[25871261]
NPO19915	Hypericum henryi	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19915	Hypericum henryi	Species	Hypericaceae	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
IC50	5

Activity Type	# Activity
Cell Line	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT116	Cell Line	HL-60	Homo sapiens	IC50	>	40000.0	nM	PMID[474590]
NPT659	Cell Line	SMMC-7721	Homo sapiens	IC50	>	40000.0	nM	PMID[474590]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	40000.0	nM	PMID[474590]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	>	40000.0	nM	PMID[474590]
NPT660	Cell Line	SW480	Homo sapiens	IC50	>	40000.0	nM	PMID[474590]

☑ 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 NPC472686 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	249
0.1-0.2	2023
0.2-0.3	8885
0.3-0.4	15728
0.4-0.5	8193
0.5-0.6	6172
0.6-0.7	1390
0.7-0.8	50
0.8-0.85	1
0.85-0.9	0
0.9-0.95	4
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC290329
0.8876	High Similarity	NPC472674
0.8876	High Similarity	NPC121036
0.8293	Intermediate Similarity	NPC266124
0.7882	Intermediate Similarity	NPC28319
0.7766	Intermediate Similarity	NPC31021
0.7732	Intermediate Similarity	NPC472685
0.7732	Intermediate Similarity	NPC472702
0.7667	Intermediate Similarity	NPC279859
0.7667	Intermediate Similarity	NPC38576
0.7629	Intermediate Similarity	NPC474802
0.7582	Intermediate Similarity	NPC471739
0.7526	Intermediate Similarity	NPC54843
0.75	Intermediate Similarity	NPC286229
0.75	Intermediate Similarity	NPC269492
0.7471	Intermediate Similarity	NPC622
0.7471	Intermediate Similarity	NPC276647
0.7471	Intermediate Similarity	NPC471740
0.7396	Intermediate Similarity	NPC474490
0.7381	Intermediate Similarity	NPC470237
0.734	Intermediate Similarity	NPC471818
0.734	Intermediate Similarity	NPC329857
0.734	Intermediate Similarity	NPC469718
0.7327	Intermediate Similarity	NPC472756
0.7326	Intermediate Similarity	NPC474527
0.7326	Intermediate Similarity	NPC471726
0.732	Intermediate Similarity	NPC476275
0.7263	Intermediate Similarity	NPC20713
0.7253	Intermediate Similarity	NPC475796
0.7248	Intermediate Similarity	NPC94425
0.7241	Intermediate Similarity	NPC476264
0.7241	Intermediate Similarity	NPC476325
0.7241	Intermediate Similarity	NPC122264
0.7228	Intermediate Similarity	NPC271059
0.7228	Intermediate Similarity	NPC25666
0.7209	Intermediate Similarity	NPC324762
0.7204	Intermediate Similarity	NPC38885
0.72	Intermediate Similarity	NPC323441
0.7195	Intermediate Similarity	NPC469868
0.7191	Intermediate Similarity	NPC304795
0.7188	Intermediate Similarity	NPC475302
0.7188	Intermediate Similarity	NPC202824
0.7188	Intermediate Similarity	NPC477361
0.7172	Intermediate Similarity	NPC470188
0.7143	Intermediate Similarity	NPC475622
0.7143	Intermediate Similarity	NPC108045
0.7143	Intermediate Similarity	NPC477354
0.7143	Intermediate Similarity	NPC472955
0.7143	Intermediate Similarity	NPC318082
0.7143	Intermediate Similarity	NPC222358
0.7129	Intermediate Similarity	NPC105725
0.7128	Intermediate Similarity	NPC471047
0.7128	Intermediate Similarity	NPC475906
0.7128	Intermediate Similarity	NPC469628
0.7128	Intermediate Similarity	NPC469631
0.7128	Intermediate Similarity	NPC469653
0.7113	Intermediate Similarity	NPC148463
0.7111	Intermediate Similarity	NPC474353
0.7097	Intermediate Similarity	NPC477479
0.7097	Intermediate Similarity	NPC104961
0.7097	Intermediate Similarity	NPC70422
0.7097	Intermediate Similarity	NPC477478
0.7097	Intermediate Similarity	NPC70555
0.7083	Intermediate Similarity	NPC150978
0.7083	Intermediate Similarity	NPC74103
0.7083	Intermediate Similarity	NPC327515
0.7083	Intermediate Similarity	NPC70595
0.7083	Intermediate Similarity	NPC123177
0.7053	Intermediate Similarity	NPC305039
0.7041	Intermediate Similarity	NPC474947
0.7033	Intermediate Similarity	NPC240302
0.7033	Intermediate Similarity	NPC173609
0.7033	Intermediate Similarity	NPC471326
0.7033	Intermediate Similarity	NPC221231
0.703	Intermediate Similarity	NPC472753
0.7024	Intermediate Similarity	NPC144511
0.7024	Intermediate Similarity	NPC296522
0.7021	Intermediate Similarity	NPC197333
0.701	Intermediate Similarity	NPC476598
0.701	Intermediate Similarity	NPC165383
0.701	Intermediate Similarity	NPC476597
0.699	Remote Similarity	NPC325769
0.6989	Remote Similarity	NPC21471
0.6989	Remote Similarity	NPC33570
0.6979	Remote Similarity	NPC263977
0.6979	Remote Similarity	NPC51653
0.6979	Remote Similarity	NPC253144
0.6966	Remote Similarity	NPC35574
0.6966	Remote Similarity	NPC474056
0.6961	Remote Similarity	NPC472754
0.6961	Remote Similarity	NPC49393
0.6961	Remote Similarity	NPC78127
0.6961	Remote Similarity	NPC471757
0.6957	Remote Similarity	NPC475989
0.6957	Remote Similarity	NPC474703
0.6957	Remote Similarity	NPC215294
0.6957	Remote Similarity	NPC477373
0.6947	Remote Similarity	NPC475902
0.6939	Remote Similarity	NPC469819
0.6939	Remote Similarity	NPC114162
0.6939	Remote Similarity	NPC476596
0.6932	Remote Similarity	NPC226242
0.6931	Remote Similarity	NPC472728
0.6931	Remote Similarity	NPC472727
0.6923	Remote Similarity	NPC476988
0.6923	Remote Similarity	NPC39411
0.6923	Remote Similarity	NPC255580
0.6923	Remote Similarity	NPC292588
0.6923	Remote Similarity	NPC327002
0.6915	Remote Similarity	NPC202394
0.6907	Remote Similarity	NPC284185
0.69	Remote Similarity	NPC87090
0.6893	Remote Similarity	NPC474166
0.6893	Remote Similarity	NPC472755
0.6893	Remote Similarity	NPC19239
0.6893	Remote Similarity	NPC475873
0.6889	Remote Similarity	NPC82488
0.6889	Remote Similarity	NPC308545
0.6889	Remote Similarity	NPC469620
0.6889	Remote Similarity	NPC469690
0.6887	Remote Similarity	NPC23497
0.6887	Remote Similarity	NPC220705
0.6882	Remote Similarity	NPC149869
0.6882	Remote Similarity	NPC474359
0.6882	Remote Similarity	NPC469569
0.6882	Remote Similarity	NPC100391
0.6875	Remote Similarity	NPC473039
0.6875	Remote Similarity	NPC474570
0.6867	Remote Similarity	NPC126899
0.6867	Remote Similarity	NPC154728
0.6867	Remote Similarity	NPC304665
0.6863	Remote Similarity	NPC101067
0.6863	Remote Similarity	NPC476134
0.6863	Remote Similarity	NPC477356
0.686	Remote Similarity	NPC40327
0.6854	Remote Similarity	NPC15975
0.6854	Remote Similarity	NPC476794
0.6854	Remote Similarity	NPC195785
0.6854	Remote Similarity	NPC145898
0.6854	Remote Similarity	NPC470240
0.6842	Remote Similarity	NPC179659
0.6842	Remote Similarity	NPC478145
0.6842	Remote Similarity	NPC171722
0.6842	Remote Similarity	NPC471738
0.6837	Remote Similarity	NPC248193
0.6832	Remote Similarity	NPC112753
0.6832	Remote Similarity	NPC472730
0.6832	Remote Similarity	NPC477355
0.6832	Remote Similarity	NPC275439
0.6832	Remote Similarity	NPC472729
0.6832	Remote Similarity	NPC153776
0.6832	Remote Similarity	NPC177680
0.6827	Remote Similarity	NPC13385
0.6824	Remote Similarity	NPC199557
0.6818	Remote Similarity	NPC474419
0.6818	Remote Similarity	NPC244166
0.6818	Remote Similarity	NPC475861
0.6813	Remote Similarity	NPC223904
0.6813	Remote Similarity	NPC47747
0.6809	Remote Similarity	NPC96621
0.6809	Remote Similarity	NPC161957
0.6809	Remote Similarity	NPC470223
0.6804	Remote Similarity	NPC316228
0.68	Remote Similarity	NPC184065
0.6796	Remote Similarity	NPC118405
0.6792	Remote Similarity	NPC169888
0.6792	Remote Similarity	NPC473939
0.6792	Remote Similarity	NPC55972
0.6792	Remote Similarity	NPC469508
0.6792	Remote Similarity	NPC327286
0.6792	Remote Similarity	NPC473595
0.6789	Remote Similarity	NPC326264
0.6789	Remote Similarity	NPC472929
0.6782	Remote Similarity	NPC92909
0.6782	Remote Similarity	NPC107783
0.6778	Remote Similarity	NPC478247
0.6778	Remote Similarity	NPC321514
0.6778	Remote Similarity	NPC478246
0.6774	Remote Similarity	NPC318468
0.6771	Remote Similarity	NPC190718
0.6771	Remote Similarity	NPC241507
0.6771	Remote Similarity	NPC53158
0.6768	Remote Similarity	NPC167219
0.6768	Remote Similarity	NPC469632
0.6768	Remote Similarity	NPC121825
0.6765	Remote Similarity	NPC46761
0.6762	Remote Similarity	NPC9303
0.6762	Remote Similarity	NPC16313
0.6762	Remote Similarity	NPC475802
0.6744	Remote Similarity	NPC475310
0.6742	Remote Similarity	NPC41017
0.6739	Remote Similarity	NPC44963
0.6739	Remote Similarity	NPC141810
0.6739	Remote Similarity	NPC472684
0.6739	Remote Similarity	NPC475665
0.6739	Remote Similarity	NPC471325
0.6739	Remote Similarity	NPC189237
0.6739	Remote Similarity	NPC281949
0.6739	Remote Similarity	NPC25684
0.6739	Remote Similarity	NPC301477

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 NPC472686 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	248
0.1-0.2	2666
0.2-0.3	3965
0.3-0.4	1558
0.4-0.5	432
0.5-0.6	232
0.6-0.7	49
0.7-0.8	0
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
0.7097	Intermediate Similarity	NPD6098	Approved
0.7053	Intermediate Similarity	NPD6904	Approved
0.7053	Intermediate Similarity	NPD6080	Approved
0.7053	Intermediate Similarity	NPD6673	Approved
0.6947	Remote Similarity	NPD6672	Approved
0.6947	Remote Similarity	NPD5737	Approved
0.6923	Remote Similarity	NPD5369	Approved
0.6907	Remote Similarity	NPD6050	Approved
0.6832	Remote Similarity	NPD5696	Approved
0.6804	Remote Similarity	NPD5692	Phase 3
0.6768	Remote Similarity	NPD5282	Discontinued
0.6735	Remote Similarity	NPD5694	Approved
0.6735	Remote Similarity	NPD5693	Phase 1
0.67	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6569	Remote Similarity	NPD6084	Phase 2
0.6569	Remote Similarity	NPD6083	Phase 2
0.6566	Remote Similarity	NPD6411	Approved
0.6562	Remote Similarity	NPD5786	Approved
0.6542	Remote Similarity	NPD6614	Approved
0.6535	Remote Similarity	NPD5695	Phase 3
0.6535	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.65	Remote Similarity	NPD6399	Phase 3
0.6489	Remote Similarity	NPD4270	Approved
0.6489	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.6489	Remote Similarity	NPD4269	Approved
0.6465	Remote Similarity	NPD5785	Approved
0.6465	Remote Similarity	NPD5207	Approved
0.6392	Remote Similarity	NPD7521	Approved
0.6392	Remote Similarity	NPD7146	Approved
0.6392	Remote Similarity	NPD6409	Approved
0.6392	Remote Similarity	NPD7334	Approved
0.6392	Remote Similarity	NPD6684	Approved
0.6392	Remote Similarity	NPD5330	Approved
0.6389	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6373	Remote Similarity	NPD5654	Approved
0.6364	Remote Similarity	NPD6101	Approved
0.6364	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6327	Remote Similarity	NPD3573	Approved
0.6316	Remote Similarity	NPD6435	Approved
0.6316	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6296	Remote Similarity	NPD5739	Approved
0.6296	Remote Similarity	NPD6675	Approved
0.6296	Remote Similarity	NPD7128	Approved
0.6296	Remote Similarity	NPD6402	Approved
0.6289	Remote Similarity	NPD1694	Approved
0.6289	Remote Similarity	NPD5363	Approved
0.6277	Remote Similarity	NPD4252	Approved
0.6277	Remote Similarity	NPD4695	Discontinued
0.6275	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6275	Remote Similarity	NPD6001	Approved
0.6275	Remote Similarity	NPD7900	Approved
0.6273	Remote Similarity	NPD6373	Approved
0.6273	Remote Similarity	NPD6372	Approved
0.6264	Remote Similarity	NPD8039	Approved
0.6263	Remote Similarity	NPD6903	Approved
0.6263	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6263	Remote Similarity	NPD5208	Approved
0.625	Remote Similarity	NPD5959	Approved
0.6237	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.62	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6182	Remote Similarity	NPD6881	Approved
0.6182	Remote Similarity	NPD6899	Approved
0.6182	Remote Similarity	NPD7320	Approved
0.6176	Remote Similarity	NPD5778	Approved
0.6176	Remote Similarity	NPD5779	Approved
0.6161	Remote Similarity	NPD6649	Approved
0.6161	Remote Similarity	NPD6650	Approved
0.6161	Remote Similarity	NPD8130	Phase 1
0.6154	Remote Similarity	NPD7732	Phase 3
0.6147	Remote Similarity	NPD6008	Approved
0.6146	Remote Similarity	NPD5209	Approved
0.6122	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6122	Remote Similarity	NPD5329	Approved
0.6117	Remote Similarity	NPD7748	Approved
0.6111	Remote Similarity	NPD6052	Approved
0.6106	Remote Similarity	NPD8297	Approved
0.6105	Remote Similarity	NPD5368	Approved
0.6095	Remote Similarity	NPD7902	Approved
0.6092	Remote Similarity	NPD7331	Phase 2
0.6091	Remote Similarity	NPD5701	Approved
0.6091	Remote Similarity	NPD5697	Approved
0.6082	Remote Similarity	NPD7154	Phase 3
0.6082	Remote Similarity	NPD5362	Discontinued
0.6078	Remote Similarity	NPD5284	Approved
0.6078	Remote Similarity	NPD5281	Approved
0.6078	Remote Similarity	NPD7983	Approved
0.6071	Remote Similarity	NPD7290	Approved
0.6071	Remote Similarity	NPD7102	Approved
0.6071	Remote Similarity	NPD6883	Approved
0.6071	Remote Similarity	NPD6371	Approved
0.6061	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6058	Remote Similarity	NPD5210	Approved
0.6058	Remote Similarity	NPD4629	Approved
0.604	Remote Similarity	NPD1695	Approved
0.6036	Remote Similarity	NPD6011	Approved
0.602	Remote Similarity	NPD4197	Approved
0.6018	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6018	Remote Similarity	NPD6847	Approved
0.6018	Remote Similarity	NPD6869	Approved
0.6018	Remote Similarity	NPD6617	Approved
0.5982	Remote Similarity	NPD6014	Approved
0.5982	Remote Similarity	NPD6012	Approved
0.5982	Remote Similarity	NPD6013	Approved
0.5977	Remote Similarity	NPD7341	Phase 2
0.5965	Remote Similarity	NPD6882	Approved
0.5909	Remote Similarity	NPD6108	Clinical (unspecified phase)
0.59	Remote Similarity	NPD5690	Phase 2
0.59	Remote Similarity	NPD5280	Approved
0.59	Remote Similarity	NPD4694	Approved
0.5888	Remote Similarity	NPD4225	Approved
0.5882	Remote Similarity	NPD4753	Phase 2
0.5859	Remote Similarity	NPD4786	Approved
0.5859	Remote Similarity	NPD3668	Phase 3
0.5854	Remote Similarity	NPD8293	Discontinued
0.5849	Remote Similarity	NPD7839	Suspended
0.5849	Remote Similarity	NPD7614	Phase 1
0.582	Remote Similarity	NPD7492	Approved
0.5816	Remote Similarity	NPD4221	Approved
0.5816	Remote Similarity	NPD4223	Phase 3
0.5816	Remote Similarity	NPD3667	Approved
0.5806	Remote Similarity	NPD7736	Approved
0.5789	Remote Similarity	NPD4756	Discovery
0.5773	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.5773	Remote Similarity	NPD4821	Approved
0.5773	Remote Similarity	NPD4820	Approved
0.5773	Remote Similarity	NPD4822	Approved
0.5773	Remote Similarity	NPD4819	Approved
0.5772	Remote Similarity	NPD6616	Approved
0.5769	Remote Similarity	NPD8034	Phase 2
0.5769	Remote Similarity	NPD7515	Phase 2
0.5769	Remote Similarity	NPD7637	Suspended
0.5769	Remote Similarity	NPD8035	Phase 2
0.5763	Remote Similarity	NPD7115	Discovery
0.575	Remote Similarity	NPD6059	Approved
0.575	Remote Similarity	NPD6054	Approved
0.575	Remote Similarity	NPD29	Approved
0.575	Remote Similarity	NPD28	Approved
0.575	Remote Similarity	NPD6319	Approved
0.5743	Remote Similarity	NPD5279	Phase 3
0.5743	Remote Similarity	NPD6422	Discontinued
0.5739	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.5738	Remote Similarity	NPD8328	Phase 3
0.5729	Remote Similarity	NPD3617	Approved
0.5728	Remote Similarity	NPD5370	Suspended
0.5727	Remote Similarity	NPD5091	Approved
0.5726	Remote Similarity	NPD7078	Approved
0.5714	Remote Similarity	NPD6335	Approved
0.5714	Remote Similarity	NPD857	Phase 3
0.5701	Remote Similarity	NPD4697	Phase 3
0.5678	Remote Similarity	NPD6868	Approved
0.5678	Remote Similarity	NPD6274	Approved
0.5667	Remote Similarity	NPD7100	Approved
0.5667	Remote Similarity	NPD7101	Approved
0.5656	Remote Similarity	NPD6370	Approved
0.5648	Remote Similarity	NPD4755	Approved
0.5644	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.5631	Remote Similarity	NPD4518	Approved
0.563	Remote Similarity	NPD6317	Approved
0.563	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.5619	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.5614	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.5612	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.56	Remote Similarity	NPD5332	Approved
0.56	Remote Similarity	NPD5331	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