NPASS Compound

Structure

NPC204048 OpenBabel07101718202D 32 34 0 0 1 0 0 0 0 0999 V2000 4.6213 -0.2826 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1584 -0.9670 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7549 0.7859 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7049 -5.6174 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4698 3.0465 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5670 2.2879 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3362 1.5718 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4123 1.2716 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8310 -0.4857 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1221 -3.1142 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1923 -1.0685 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8310 0.4857 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.8064 -4.6513 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4359 2.9450 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3362 -2.5432 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2600 1.2716 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.2600 -1.2716 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.3362 -1.5718 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4123 -1.2716 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8413 -0.4857 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.7971 -1.9560 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4123 -2.8434 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8413 0.4857 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.6939 -4.2562 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.0069 3.7309 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.3681 -2.7419 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.1121 -3.7673 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.0205 -4.0803 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.8310 2.0575 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.8310 -2.0575 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8413 -2.0575 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 11 2 0 0 0 0 2 11 1 0 0 0 0 4 13 1 0 0 0 0 5 14 1 0 0 0 0 7 8 1 0 0 0 0 7 16 1 0 0 0 0 8 23 1 0 0 0 0 9 12 1 0 0 0 0 9 17 1 0 0 0 0 10 15 1 0 0 0 0 10 28 1 0 0 0 0 11 21 1 0 0 0 0 12 3 1 1 0 0 0 12 16 1 0 0 0 0 13 24 2 0 0 0 0 13 28 1 0 0 0 0 14 25 2 0 0 0 0 14 29 1 0 0 0 0 15 18 2 0 0 0 0 15 22 1 0 0 0 0 16 29 1 6 0 0 0 17 18 1 0 0 0 0 17 30 1 6 0 0 0 19 18 1 6 0 0 0 19 20 1 0 0 0 0 19 31 1 0 0 0 0 20 23 1 1 0 0 0 20 32 1 0 0 0 0 21 26 2 0 0 0 0 21 30 1 0 0 0 0 22 27 2 0 0 0 0 22 31 1 0 0 0 0 23 6 1 1 0 0 0 23 32 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	450.19
Volume:	443.988
LogP:	3.252
LogD:	2.493
LogS:	-3.327
# Rotatable Bonds:	8
TPSA:	124.8
# H-Bond Aceptor:	9
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.309
Synthetic Accessibility Score:	5.199
Fsp3:	0.609
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	3
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.204
MDCK Permeability:	6.048778959666379e-05
Pgp-inhibitor:	0.107
Pgp-substrate:	0.007
Human Intestinal Absorption (HIA):	0.08
20% Bioavailability (F20%):	0.009
30% Bioavailability (F30%):	0.886

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.434
Plasma Protein Binding (PPB):	76.13184356689453%
Volume Distribution (VD):	1.185
Pgp-substrate:	21.238582611083984%

ADMET: Metabolism

CYP1A2-inhibitor:	0.023
CYP1A2-substrate:	0.099
CYP2C19-inhibitor:	0.018
CYP2C19-substrate:	0.642
CYP2C9-inhibitor:	0.336
CYP2C9-substrate:	0.196
CYP2D6-inhibitor:	0.015
CYP2D6-substrate:	0.158
CYP3A4-inhibitor:	0.203
CYP3A4-substrate:	0.539

ADMET: Excretion

Clearance (CL):	3.528
Half-life (T1/2):	0.759

ADMET: Toxicity

hERG Blockers:	0.008
Human Hepatotoxicity (H-HT):	0.949
Drug-inuced Liver Injury (DILI):	0.944
AMES Toxicity:	0.73
Rat Oral Acute Toxicity:	0.886
Maximum Recommended Daily Dose:	0.362
Skin Sensitization:	0.607
Carcinogencity:	0.43
Eye Corrosion:	0.023
Eye Irritation:	0.073
Respiratory Toxicity:	0.96

Download Data

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

Natural Product: NPC204048

Natural Product ID:	NPC204048
*Common Name:**	Glaucolide K
IUPAC Name:	n.a.
Synonyms:	Glaucolide K
Standard InCHIKey:	SMSAHFFESNPUAJ-SAHIIEOHSA-N
Standard InCHI:	InChI=1S/C23H30O9/c1-11(2)21(26)30-17-9-12(3)16(29-14(5)25)7-8-23(6)20(32-23)19-18(17)15(22(27)31-19)10-28-13(4)24/h12,16-17,19-20H,1,7-10H2,2-6H3/t12-,16-,17-,19-,20+,23+/m0/s1
SMILES:	CC(=O)OCC1=C2[C@H](C[C@H](C)[C@H](CC[C@@]3([C@@H]([C@H]2OC1=O)O3)C)OC(=O)C)OC(=O)C(=C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL516705
PubChem CID:	11719358
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
NPO22460	Vernonia pachyclada	Species	Asteraceae	Eukaryota	n.a.	Madagascar rainforest	n.a.	PMID[16180816]
NPO22460	Vernonia pachyclada	Species	Asteraceae	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	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT179	Cell Line	A2780	Homo sapiens	IC50	=	5800.0	nM	PMID[572723]

☑ 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 NPC204048 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	260
0.1-0.2	2051
0.2-0.3	6093
0.3-0.4	15795
0.4-0.5	11099
0.5-0.6	5125
0.6-0.7	1997
0.7-0.8	268
0.8-0.85	6
0.85-0.9	1
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9412	High Similarity	NPC158061
0.8537	High Similarity	NPC23187
0.8352	Intermediate Similarity	NPC473330
0.8352	Intermediate Similarity	NPC473316
0.8352	Intermediate Similarity	NPC140543
0.8333	Intermediate Similarity	NPC474739
0.828	Intermediate Similarity	NPC471140
0.8222	Intermediate Similarity	NPC475748
0.8211	Intermediate Similarity	NPC264477
0.8211	Intermediate Similarity	NPC477511
0.8191	Intermediate Similarity	NPC208233
0.8182	Intermediate Similarity	NPC50637
0.8172	Intermediate Similarity	NPC35498
0.8172	Intermediate Similarity	NPC17585
0.8172	Intermediate Similarity	NPC279621
0.8172	Intermediate Similarity	NPC230800
0.8152	Intermediate Similarity	NPC471147
0.8152	Intermediate Similarity	NPC476267
0.8111	Intermediate Similarity	NPC166919
0.8111	Intermediate Similarity	NPC151770
0.8105	Intermediate Similarity	NPC288876
0.809	Intermediate Similarity	NPC231889
0.8065	Intermediate Similarity	NPC475659
0.8021	Intermediate Similarity	NPC474339
0.8021	Intermediate Similarity	NPC164598
0.8	Intermediate Similarity	NPC260343
0.7979	Intermediate Similarity	NPC473859
0.7959	Intermediate Similarity	NPC471143
0.7959	Intermediate Similarity	NPC477510
0.7957	Intermediate Similarity	NPC474247
0.7952	Intermediate Similarity	NPC93213
0.7917	Intermediate Similarity	NPC477512
0.7895	Intermediate Similarity	NPC471490
0.7889	Intermediate Similarity	NPC475703
0.7889	Intermediate Similarity	NPC5130
0.7872	Intermediate Similarity	NPC471141
0.7857	Intermediate Similarity	NPC301525
0.7849	Intermediate Similarity	NPC475838
0.7849	Intermediate Similarity	NPC228451
0.7849	Intermediate Similarity	NPC125674
0.7841	Intermediate Similarity	NPC231601
0.7841	Intermediate Similarity	NPC170286
0.7835	Intermediate Similarity	NPC201718
0.7826	Intermediate Similarity	NPC312042
0.7816	Intermediate Similarity	NPC141810
0.7812	Intermediate Similarity	NPC473326
0.7812	Intermediate Similarity	NPC279561
0.7805	Intermediate Similarity	NPC477084
0.7802	Intermediate Similarity	NPC475902
0.78	Intermediate Similarity	NPC477513
0.7789	Intermediate Similarity	NPC476315
0.7778	Intermediate Similarity	NPC469483
0.7755	Intermediate Similarity	NPC471148
0.7755	Intermediate Similarity	NPC149371
0.7742	Intermediate Similarity	NPC20713
0.7717	Intermediate Similarity	NPC242877
0.7717	Intermediate Similarity	NPC64913
0.7692	Intermediate Similarity	NPC476600
0.7692	Intermediate Similarity	NPC266957
0.7684	Intermediate Similarity	NPC14961
0.7684	Intermediate Similarity	NPC270013
0.7684	Intermediate Similarity	NPC471142
0.7684	Intermediate Similarity	NPC471492
0.7684	Intermediate Similarity	NPC220221
0.7667	Intermediate Similarity	NPC38468
0.7667	Intermediate Similarity	NPC474547
0.7667	Intermediate Similarity	NPC50362
0.7667	Intermediate Similarity	NPC319795
0.766	Intermediate Similarity	NPC212486
0.766	Intermediate Similarity	NPC471483
0.766	Intermediate Similarity	NPC476300
0.7654	Intermediate Similarity	NPC276290
0.7653	Intermediate Similarity	NPC47880
0.764	Intermediate Similarity	NPC475947
0.764	Intermediate Similarity	NPC272814
0.7634	Intermediate Similarity	NPC49342
0.7634	Intermediate Similarity	NPC3952
0.7634	Intermediate Similarity	NPC177668
0.7634	Intermediate Similarity	NPC251385
0.7629	Intermediate Similarity	NPC222303
0.7629	Intermediate Similarity	NPC471144
0.7629	Intermediate Similarity	NPC474213
0.7604	Intermediate Similarity	NPC475380
0.7604	Intermediate Similarity	NPC209297
0.76	Intermediate Similarity	NPC474741
0.7586	Intermediate Similarity	NPC617
0.7579	Intermediate Similarity	NPC474035
0.7579	Intermediate Similarity	NPC161998
0.7579	Intermediate Similarity	NPC81386
0.7579	Intermediate Similarity	NPC57405
0.7579	Intermediate Similarity	NPC303942
0.7561	Intermediate Similarity	NPC269841
0.7556	Intermediate Similarity	NPC470238
0.7556	Intermediate Similarity	NPC186155
0.7556	Intermediate Similarity	NPC138647
0.7556	Intermediate Similarity	NPC78673
0.7556	Intermediate Similarity	NPC160517
0.7553	Intermediate Similarity	NPC32494
0.7553	Intermediate Similarity	NPC175842
0.7551	Intermediate Similarity	NPC475949
0.7527	Intermediate Similarity	NPC133450
0.7527	Intermediate Similarity	NPC475971
0.7526	Intermediate Similarity	NPC2666
0.7526	Intermediate Similarity	NPC472998
0.7526	Intermediate Similarity	NPC311241
0.7526	Intermediate Similarity	NPC471462
0.7526	Intermediate Similarity	NPC475446
0.7525	Intermediate Similarity	NPC103088
0.7525	Intermediate Similarity	NPC470979
0.7525	Intermediate Similarity	NPC470975
0.75	Intermediate Similarity	NPC474166
0.75	Intermediate Similarity	NPC19239
0.75	Intermediate Similarity	NPC469583
0.75	Intermediate Similarity	NPC475087
0.75	Intermediate Similarity	NPC36954
0.7475	Intermediate Similarity	NPC473332
0.7474	Intermediate Similarity	NPC475912
0.7474	Intermediate Similarity	NPC165383
0.7473	Intermediate Similarity	NPC215364
0.7451	Intermediate Similarity	NPC474716
0.7449	Intermediate Similarity	NPC107806
0.7449	Intermediate Similarity	NPC161855
0.7449	Intermediate Similarity	NPC72647
0.7447	Intermediate Similarity	NPC144133
0.7447	Intermediate Similarity	NPC475855
0.7447	Intermediate Similarity	NPC179394
0.7447	Intermediate Similarity	NPC473448
0.7447	Intermediate Similarity	NPC62815
0.7447	Intermediate Similarity	NPC51004
0.7444	Intermediate Similarity	NPC170377
0.7444	Intermediate Similarity	NPC128429
0.7444	Intermediate Similarity	NPC257358
0.7444	Intermediate Similarity	NPC318468
0.7444	Intermediate Similarity	NPC474472
0.7423	Intermediate Similarity	NPC39859
0.7423	Intermediate Similarity	NPC76862
0.7423	Intermediate Similarity	NPC472997
0.7423	Intermediate Similarity	NPC472996
0.7423	Intermediate Similarity	NPC470883
0.7423	Intermediate Similarity	NPC158416
0.7423	Intermediate Similarity	NPC473333
0.7423	Intermediate Similarity	NPC472995
0.7423	Intermediate Similarity	NPC476275
0.7416	Intermediate Similarity	NPC79277
0.7416	Intermediate Similarity	NPC474894
0.7416	Intermediate Similarity	NPC475481
0.7412	Intermediate Similarity	NPC474758
0.74	Intermediate Similarity	NPC471914
0.7396	Intermediate Similarity	NPC140277
0.7396	Intermediate Similarity	NPC256368
0.7391	Intermediate Similarity	NPC284902
0.7391	Intermediate Similarity	NPC261253
0.7391	Intermediate Similarity	NPC137253
0.7391	Intermediate Similarity	NPC61527
0.7391	Intermediate Similarity	NPC474045
0.7381	Intermediate Similarity	NPC475762
0.7379	Intermediate Similarity	NPC181994
0.7374	Intermediate Similarity	NPC469551
0.7374	Intermediate Similarity	NPC13743
0.7374	Intermediate Similarity	NPC98813
0.7368	Intermediate Similarity	NPC184463
0.7368	Intermediate Similarity	NPC30515
0.7368	Intermediate Similarity	NPC70251
0.7368	Intermediate Similarity	NPC475881
0.7356	Intermediate Similarity	NPC84360
0.7353	Intermediate Similarity	NPC475802
0.7353	Intermediate Similarity	NPC16313
0.7353	Intermediate Similarity	NPC9303
0.7353	Intermediate Similarity	NPC223450
0.7349	Intermediate Similarity	NPC265574
0.7347	Intermediate Similarity	NPC199099
0.7347	Intermediate Similarity	NPC40812
0.7347	Intermediate Similarity	NPC205143
0.7347	Intermediate Similarity	NPC153559
0.7347	Intermediate Similarity	NPC100912
0.734	Intermediate Similarity	NPC307411
0.7333	Intermediate Similarity	NPC475495
0.7333	Intermediate Similarity	NPC35556
0.7327	Intermediate Similarity	NPC471938
0.7327	Intermediate Similarity	NPC475871
0.7327	Intermediate Similarity	NPC472755
0.7327	Intermediate Similarity	NPC475945
0.732	Intermediate Similarity	NPC224689
0.732	Intermediate Similarity	NPC477922
0.7317	Intermediate Similarity	NPC472266
0.7312	Intermediate Similarity	NPC160138
0.7308	Intermediate Similarity	NPC477102
0.7303	Intermediate Similarity	NPC474510
0.73	Intermediate Similarity	NPC15993
0.73	Intermediate Similarity	NPC474742
0.73	Intermediate Similarity	NPC476270
0.7292	Intermediate Similarity	NPC472195
0.7292	Intermediate Similarity	NPC238090
0.7292	Intermediate Similarity	NPC179746
0.7292	Intermediate Similarity	NPC59646
0.7292	Intermediate Similarity	NPC472196
0.7292	Intermediate Similarity	NPC81419
0.7283	Intermediate Similarity	NPC47958
0.7283	Intermediate Similarity	NPC99395
0.7283	Intermediate Similarity	NPC149725

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 NPC204048 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	259
0.1-0.2	2580
0.2-0.3	3858
0.3-0.4	1846
0.4-0.5	488
0.5-0.6	101
0.6-0.7	13
0.7-0.8	5
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
0.8022	Intermediate Similarity	NPD7838	Discovery
0.7667	Intermediate Similarity	NPD1733	Clinical (unspecified phase)
0.7634	Intermediate Similarity	NPD6698	Approved
0.7634	Intermediate Similarity	NPD46	Approved
0.7284	Intermediate Similarity	NPD2685	Clinical (unspecified phase)
0.7282	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD6648	Approved
0.7158	Intermediate Similarity	NPD1695	Approved
0.7129	Intermediate Similarity	NPD5344	Discontinued
0.7075	Intermediate Similarity	NPD6371	Approved
0.6931	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6837	Remote Similarity	NPD7983	Approved
0.6792	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD5209	Approved
0.6765	Remote Similarity	NPD4225	Approved
0.6729	Remote Similarity	NPD6686	Approved
0.6606	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6596	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6514	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6261	Remote Similarity	NPD7115	Discovery
0.625	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6238	Remote Similarity	NPD5785	Approved
0.6214	Remote Similarity	NPD5282	Discontinued
0.6162	Remote Similarity	NPD4249	Approved
0.6132	Remote Similarity	NPD7638	Approved
0.6122	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6117	Remote Similarity	NPD5779	Approved
0.6117	Remote Similarity	NPD5778	Approved
0.61	Remote Similarity	NPD4251	Approved
0.61	Remote Similarity	NPD4250	Approved
0.6083	Remote Similarity	NPD7642	Approved
0.6083	Remote Similarity	NPD7829	Approved
0.6083	Remote Similarity	NPD7830	Approved
0.6075	Remote Similarity	NPD7640	Approved
0.6075	Remote Similarity	NPD7639	Approved
0.6068	Remote Similarity	NPD7328	Approved
0.6068	Remote Similarity	NPD7327	Approved
0.6061	Remote Similarity	NPD1694	Approved
0.6061	Remote Similarity	NPD5363	Approved
0.6061	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6053	Remote Similarity	NPD6053	Discontinued
0.605	Remote Similarity	NPD8033	Approved
0.6042	Remote Similarity	NPD4821	Approved
0.6042	Remote Similarity	NPD4820	Approved
0.6042	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6042	Remote Similarity	NPD4822	Approved
0.6042	Remote Similarity	NPD4819	Approved
0.602	Remote Similarity	NPD7154	Phase 3
0.6019	Remote Similarity	NPD7637	Suspended
0.6017	Remote Similarity	NPD7516	Approved
0.5984	Remote Similarity	NPD8273	Phase 1
0.5968	Remote Similarity	NPD7319	Approved
0.5966	Remote Similarity	NPD8294	Approved
0.5966	Remote Similarity	NPD8377	Approved
0.5946	Remote Similarity	NPD6008	Approved
0.5943	Remote Similarity	NPD7839	Suspended
0.5922	Remote Similarity	NPD3168	Discontinued
0.5917	Remote Similarity	NPD8516	Approved
0.5917	Remote Similarity	NPD8335	Approved
0.5917	Remote Similarity	NPD8378	Approved
0.5917	Remote Similarity	NPD7503	Approved
0.5917	Remote Similarity	NPD8380	Approved
0.5917	Remote Similarity	NPD8517	Approved
0.5917	Remote Similarity	NPD8379	Approved
0.5917	Remote Similarity	NPD8515	Approved
0.5917	Remote Similarity	NPD8513	Phase 3
0.5917	Remote Similarity	NPD8296	Approved
0.5854	Remote Similarity	NPD7507	Approved
0.5833	Remote Similarity	NPD4268	Approved
0.5833	Remote Similarity	NPD6319	Approved
0.5833	Remote Similarity	NPD4271	Approved
0.5825	Remote Similarity	NPD6051	Approved
0.5816	Remote Similarity	NPD5369	Approved
0.5758	Remote Similarity	NPD4270	Approved
0.5758	Remote Similarity	NPD4269	Approved
0.5714	Remote Similarity	NPD7505	Discontinued
0.5714	Remote Similarity	NPD7500	Approved
0.57	Remote Similarity	NPD5362	Discontinued
0.569	Remote Similarity	NPD2204	Approved
0.5686	Remote Similarity	NPD5786	Approved
0.5684	Remote Similarity	NPD8039	Approved
0.568	Remote Similarity	NPD8074	Phase 3
0.5676	Remote Similarity	NPD3653	Clinical (unspecified phase)
0.5676	Remote Similarity	NPD7632	Discontinued
0.5673	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.5673	Remote Similarity	NPD6101	Approved
0.5649	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.5644	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.5631	Remote Similarity	NPD7524	Approved
0.561	Remote Similarity	NPD8080	Discontinued
0.5603	Remote Similarity	NPD2067	Discontinued
0.56	Remote Similarity	NPD8451	Approved
0.56	Remote Similarity	NPD6435	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