NPASS Compound

Structure

NPC169205 OpenBabel07101718202D 26 28 0 0 1 0 0 0 0 0999 V2000 -2.9481 1.5382 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0464 -5.3088 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2611 -2.4847 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7187 -6.2744 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9624 -1.1770 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0928 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4722 -0.8878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5636 0.6683 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5291 0.6683 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.8825 -4.8261 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3476 -1.5231 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7187 -5.3088 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.1311 -0.0865 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.9616 -0.0865 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.7451 -1.5231 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1765 -1.0279 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.0464 -1.4468 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.8825 -3.8606 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3795 -0.8878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9163 -1.0279 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.5549 -4.8261 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.8317 -2.4847 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.7187 -3.3778 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3208 -1.1027 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 -2.0464 -3.3778 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 10 2 0 0 0 0 3 11 2 0 0 0 0 6 7 2 0 0 0 0 6 13 1 0 0 0 0 7 15 1 0 0 0 0 8 9 1 0 0 0 0 9 1 1 6 0 0 0 9 13 1 0 0 0 0 10 12 1 0 0 0 0 10 18 1 0 0 0 0 11 19 1 0 0 0 0 12 4 1 1 0 0 0 12 21 1 0 0 0 0 13 20 1 1 0 0 0 14 8 1 1 0 0 0 14 16 1 0 0 0 0 14 25 1 0 0 0 0 15 20 1 0 0 0 0 15 22 2 0 0 0 0 16 11 1 1 0 0 0 16 17 1 0 0 0 0 17 20 1 6 0 0 0 17 26 1 0 0 0 0 18 23 2 0 0 0 0 18 26 1 0 0 0 0 19 24 2 0 0 0 0 19 25 1 0 0 0 0 20 5 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	360.16
Volume:	365.729
LogP:	0.744
LogD:	0.532
LogS:	-2.425
# Rotatable Bonds:	4
TPSA:	89.9
# H-Bond Aceptor:	6
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.469
Synthetic Accessibility Score:	5.05
Fsp3:	0.55
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	2
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.835
MDCK Permeability:	1.8252305380883627e-05
Pgp-inhibitor:	0.992
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.584
20% Bioavailability (F20%):	0.867
30% Bioavailability (F30%):	0.979

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.512
Plasma Protein Binding (PPB):	76.2636489868164%
Volume Distribution (VD):	1.042
Pgp-substrate:	26.899641036987305%

ADMET: Metabolism

CYP1A2-inhibitor:	0.072
CYP1A2-substrate:	0.092
CYP2C19-inhibitor:	0.089
CYP2C19-substrate:	0.413
CYP2C9-inhibitor:	0.534
CYP2C9-substrate:	0.109
CYP2D6-inhibitor:	0.006
CYP2D6-substrate:	0.068
CYP3A4-inhibitor:	0.813
CYP3A4-substrate:	0.215

ADMET: Excretion

Clearance (CL):	5.619
Half-life (T1/2):	0.809

ADMET: Toxicity

hERG Blockers:	0.003
Human Hepatotoxicity (H-HT):	0.478
Drug-inuced Liver Injury (DILI):	0.891
AMES Toxicity:	0.03
Rat Oral Acute Toxicity:	0.863
Maximum Recommended Daily Dose:	0.907
Skin Sensitization:	0.723
Carcinogencity:	0.724
Eye Corrosion:	0.57
Eye Irritation:	0.639
Respiratory Toxicity:	0.967

Download Data

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

Natural Product: NPC169205

Natural Product ID:	NPC169205
*Common Name:**	Helenalin-[2-(1-Hydroxyethyl)Acrylate]
IUPAC Name:	[(3aR,5R,5aR,8aR,9S,9aR)-5,8a-dimethyl-1-methylidene-2,8-dioxo-3a,4,5,5a,9,9a-hexahydroazuleno[6,5-b]furan-9-yl] (3R)-3-hydroxy-2-methylidenebutanoate
Synonyms:
Standard InCHIKey:	SUQFZABZUSAQSY-MMTKZGGZSA-N
Standard InCHI:	InChI=1S/C20H24O6/c1-9-8-14-16(11(3)19(24)25-14)17(26-18(23)10(2)12(4)21)20(5)13(9)6-7-15(20)22/h6-7,9,12-14,16-17,21H,2-3,8H2,1,4-5H3/t9-,12-,13+,14-,16-,17+,20+/m1/s1
SMILES:	C[C@@H]1C[C@H]2OC(=O)C(=C)[C@H]2[C@@H]([C@]2([C@H]1C=CC2=O)C)OC(=O)C(=C)[C@H](O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL463958
PubChem CID:	11291363
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones [CHEMONTID:0001543] Sesquiterpene 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
NPO24121	Vernoniopsis caudata	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[15921436]
NPO24121	Vernoniopsis caudata	n.a.	n.a.	n.a.	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	2

Activity Type	# Activity
Cell Line	1
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	IC50	=	330.0	nM	PMID[554055]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	1000.0	nM	PMID[554055]

☑ 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 NPC169205 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	214
0.1-0.2	1196
0.2-0.3	4942
0.3-0.4	9653
0.4-0.5	13678
0.5-0.6	7156
0.6-0.7	4631
0.7-0.8	1086
0.8-0.85	90
0.85-0.9	30
0.9-0.95	14
0.95-1	7

Similarity Score	Similarity Level	Natural Product ID
0.989	High Similarity	NPC141191
0.9889	High Similarity	NPC185553
0.9778	High Similarity	NPC48803
0.9778	High Similarity	NPC90121
0.9778	High Similarity	NPC275960
0.9778	High Similarity	NPC193645
0.9444	High Similarity	NPC123177
0.9444	High Similarity	NPC70595
0.9444	High Similarity	NPC150978
0.9444	High Similarity	NPC74103
0.9333	High Similarity	NPC253144
0.9239	High Similarity	NPC167219
0.9231	High Similarity	NPC284185
0.9222	High Similarity	NPC52198
0.9222	High Similarity	NPC117405
0.9175	High Similarity	NPC203659
0.9167	High Similarity	NPC225353
0.9072	High Similarity	NPC110989
0.9022	High Similarity	NPC111114
0.9022	High Similarity	NPC300312
0.9022	High Similarity	NPC261607
0.8889	High Similarity	NPC70555
0.8889	High Similarity	NPC104961
0.8889	High Similarity	NPC70422
0.8854	High Similarity	NPC54843
0.883	High Similarity	NPC289004
0.8804	High Similarity	NPC12872
0.8804	High Similarity	NPC168679
0.8778	High Similarity	NPC161957
0.8778	High Similarity	NPC21471
0.8778	High Similarity	NPC33570
0.8737	High Similarity	NPC304886
0.871	High Similarity	NPC129419
0.8673	High Similarity	NPC171759
0.8602	High Similarity	NPC268298
0.8586	High Similarity	NPC474747
0.8556	High Similarity	NPC39588
0.85	High Similarity	NPC475871
0.85	High Similarity	NPC475945
0.8485	Intermediate Similarity	NPC477950
0.8478	Intermediate Similarity	NPC238593
0.8454	Intermediate Similarity	NPC142529
0.8454	Intermediate Similarity	NPC91771
0.8416	Intermediate Similarity	NPC309190
0.8416	Intermediate Similarity	NPC100487
0.8387	Intermediate Similarity	NPC237540
0.837	Intermediate Similarity	NPC165162
0.8367	Intermediate Similarity	NPC108475
0.8367	Intermediate Similarity	NPC213947
0.8367	Intermediate Similarity	NPC170143
0.8352	Intermediate Similarity	NPC215294
0.8333	Intermediate Similarity	NPC135776
0.8316	Intermediate Similarity	NPC469368
0.8316	Intermediate Similarity	NPC71533
0.8316	Intermediate Similarity	NPC106510
0.83	Intermediate Similarity	NPC110443
0.83	Intermediate Similarity	NPC133907
0.83	Intermediate Similarity	NPC46998
0.83	Intermediate Similarity	NPC128733
0.83	Intermediate Similarity	NPC474742
0.83	Intermediate Similarity	NPC185141
0.8298	Intermediate Similarity	NPC476805
0.828	Intermediate Similarity	NPC107787
0.828	Intermediate Similarity	NPC305475
0.828	Intermediate Similarity	NPC309757
0.828	Intermediate Similarity	NPC475461
0.828	Intermediate Similarity	NPC236692
0.8265	Intermediate Similarity	NPC126156
0.8261	Intermediate Similarity	NPC165287
0.8261	Intermediate Similarity	NPC115786
0.8247	Intermediate Similarity	NPC469632
0.8247	Intermediate Similarity	NPC477131
0.8247	Intermediate Similarity	NPC198853
0.8235	Intermediate Similarity	NPC474741
0.8229	Intermediate Similarity	NPC131209
0.8229	Intermediate Similarity	NPC133698
0.8222	Intermediate Similarity	NPC223904
0.8211	Intermediate Similarity	NPC295312
0.8191	Intermediate Similarity	NPC72513
0.8191	Intermediate Similarity	NPC201658
0.8182	Intermediate Similarity	NPC474343
0.8172	Intermediate Similarity	NPC255307
0.8172	Intermediate Similarity	NPC78089
0.8172	Intermediate Similarity	NPC470755
0.8172	Intermediate Similarity	NPC125290
0.8155	Intermediate Similarity	NPC243998
0.8152	Intermediate Similarity	NPC54468
0.8144	Intermediate Similarity	NPC153590
0.8144	Intermediate Similarity	NPC469645
0.8144	Intermediate Similarity	NPC308656
0.8144	Intermediate Similarity	NPC200237
0.8144	Intermediate Similarity	NPC473273
0.8144	Intermediate Similarity	NPC60386
0.8144	Intermediate Similarity	NPC473234
0.8144	Intermediate Similarity	NPC469692
0.8144	Intermediate Similarity	NPC473263
0.8144	Intermediate Similarity	NPC475302
0.8137	Intermediate Similarity	NPC475873
0.8137	Intermediate Similarity	NPC472755
0.8131	Intermediate Similarity	NPC209058
0.8125	Intermediate Similarity	NPC145666
0.8125	Intermediate Similarity	NPC19087
0.8119	Intermediate Similarity	NPC244456
0.8119	Intermediate Similarity	NPC472753
0.8119	Intermediate Similarity	NPC469657
0.8105	Intermediate Similarity	NPC476803
0.8095	Intermediate Similarity	NPC47951
0.8085	Intermediate Similarity	NPC150755
0.8081	Intermediate Similarity	NPC18019
0.8081	Intermediate Similarity	NPC24956
0.8065	Intermediate Similarity	NPC476804
0.8065	Intermediate Similarity	NPC96259
0.8065	Intermediate Similarity	NPC141193
0.8065	Intermediate Similarity	NPC158756
0.8065	Intermediate Similarity	NPC191476
0.8065	Intermediate Similarity	NPC114979
0.8061	Intermediate Similarity	NPC323008
0.8061	Intermediate Similarity	NPC53685
0.8061	Intermediate Similarity	NPC473331
0.8061	Intermediate Similarity	NPC262133
0.8061	Intermediate Similarity	NPC470013
0.8061	Intermediate Similarity	NPC470010
0.8061	Intermediate Similarity	NPC121825
0.8043	Intermediate Similarity	NPC89555
0.8041	Intermediate Similarity	NPC475925
0.8041	Intermediate Similarity	NPC286341
0.8041	Intermediate Similarity	NPC191339
0.8041	Intermediate Similarity	NPC184063
0.8039	Intermediate Similarity	NPC472754
0.8039	Intermediate Similarity	NPC86077
0.8037	Intermediate Similarity	NPC76550
0.8037	Intermediate Similarity	NPC138757
0.8037	Intermediate Similarity	NPC123855
0.8022	Intermediate Similarity	NPC74673
0.8022	Intermediate Similarity	NPC69271
0.8021	Intermediate Similarity	NPC32922
0.8021	Intermediate Similarity	NPC38392
0.802	Intermediate Similarity	NPC288876
0.8019	Intermediate Similarity	NPC257240
0.8	Intermediate Similarity	NPC477949
0.7981	Intermediate Similarity	NPC223450
0.798	Intermediate Similarity	NPC471142
0.7979	Intermediate Similarity	NPC261380
0.7963	Intermediate Similarity	NPC106395
0.7963	Intermediate Similarity	NPC46269
0.7959	Intermediate Similarity	NPC475912
0.7959	Intermediate Similarity	NPC295204
0.7959	Intermediate Similarity	NPC273579
0.7959	Intermediate Similarity	NPC288240
0.7959	Intermediate Similarity	NPC162205
0.7957	Intermediate Similarity	NPC473390
0.7957	Intermediate Similarity	NPC169575
0.7957	Intermediate Similarity	NPC131669
0.7957	Intermediate Similarity	NPC40746
0.7941	Intermediate Similarity	NPC47880
0.7941	Intermediate Similarity	NPC206079
0.7938	Intermediate Similarity	NPC179394
0.7938	Intermediate Similarity	NPC62815
0.7938	Intermediate Similarity	NPC54065
0.7938	Intermediate Similarity	NPC297474
0.7938	Intermediate Similarity	NPC77337
0.7938	Intermediate Similarity	NPC473455
0.7938	Intermediate Similarity	NPC144133
0.7938	Intermediate Similarity	NPC475855
0.7935	Intermediate Similarity	NPC470241
0.7935	Intermediate Similarity	NPC39411
0.7935	Intermediate Similarity	NPC25684
0.7935	Intermediate Similarity	NPC255580
0.7935	Intermediate Similarity	NPC35089
0.7935	Intermediate Similarity	NPC281949
0.7935	Intermediate Similarity	NPC301477
0.7935	Intermediate Similarity	NPC10276
0.7921	Intermediate Similarity	NPC64742
0.7921	Intermediate Similarity	NPC316598
0.7917	Intermediate Similarity	NPC202672
0.7917	Intermediate Similarity	NPC207114
0.7917	Intermediate Similarity	NPC475819
0.7917	Intermediate Similarity	NPC217983
0.7912	Intermediate Similarity	NPC470244
0.7912	Intermediate Similarity	NPC470239
0.79	Intermediate Similarity	NPC230800
0.79	Intermediate Similarity	NPC476009
0.79	Intermediate Similarity	NPC184065
0.7895	Intermediate Similarity	NPC469910
0.7895	Intermediate Similarity	NPC261721
0.789	Intermediate Similarity	NPC133677
0.789	Intermediate Similarity	NPC67290
0.789	Intermediate Similarity	NPC138303
0.7885	Intermediate Similarity	NPC472756
0.7879	Intermediate Similarity	NPC65829
0.7864	Intermediate Similarity	NPC149371
0.7857	Intermediate Similarity	NPC472814
0.7857	Intermediate Similarity	NPC12172
0.7857	Intermediate Similarity	NPC171360
0.7857	Intermediate Similarity	NPC177037
0.7857	Intermediate Similarity	NPC208886
0.7857	Intermediate Similarity	NPC63193
0.7857	Intermediate Similarity	NPC133888
0.7857	Intermediate Similarity	NPC184463
0.7857	Intermediate Similarity	NPC219874

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 NPC169205 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	195
0.1-0.2	1775
0.2-0.3	3700
0.3-0.4	2349
0.4-0.5	673
0.5-0.6	307
0.6-0.7	129
0.7-0.8	18
0.8-0.85	3
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9778	High Similarity	NPD1698	Clinical (unspecified phase)
0.8125	Intermediate Similarity	NPD5785	Approved
0.8019	Intermediate Similarity	NPD6371	Approved
0.7736	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.77	Intermediate Similarity	NPD5282	Discontinued
0.7604	Intermediate Similarity	NPD5363	Approved
0.7573	Intermediate Similarity	NPD4225	Approved
0.7526	Intermediate Similarity	NPD5786	Approved
0.7475	Intermediate Similarity	NPD1695	Approved
0.7327	Intermediate Similarity	NPD6411	Approved
0.7292	Intermediate Similarity	NPD6435	Approved
0.7292	Intermediate Similarity	NPD4270	Approved
0.7292	Intermediate Similarity	NPD5209	Approved
0.7292	Intermediate Similarity	NPD4269	Approved
0.7255	Intermediate Similarity	NPD5779	Approved
0.7255	Intermediate Similarity	NPD5778	Approved
0.7245	Intermediate Similarity	NPD1694	Approved
0.7216	Intermediate Similarity	NPD5362	Discontinued
0.7216	Intermediate Similarity	NPD7154	Phase 3
0.7188	Intermediate Similarity	NPD5369	Approved
0.7157	Intermediate Similarity	NPD7983	Approved
0.713	Intermediate Similarity	NPD7115	Discovery
0.7129	Intermediate Similarity	NPD6101	Approved
0.7129	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD5368	Approved
0.7083	Intermediate Similarity	NPD4252	Approved
0.7053	Intermediate Similarity	NPD5784	Clinical (unspecified phase)
0.6939	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6937	Remote Similarity	NPD5697	Approved
0.6907	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.69	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6893	Remote Similarity	NPD6698	Approved
0.6893	Remote Similarity	NPD46	Approved
0.6875	Remote Similarity	NPD6881	Approved
0.6875	Remote Similarity	NPD6899	Approved
0.6842	Remote Similarity	NPD6649	Approved
0.6842	Remote Similarity	NPD6650	Approved
0.6832	Remote Similarity	NPD4249	Approved
0.6814	Remote Similarity	NPD6013	Approved
0.6814	Remote Similarity	NPD6014	Approved
0.6814	Remote Similarity	NPD6012	Approved
0.6783	Remote Similarity	NPD6053	Discontinued
0.6765	Remote Similarity	NPD4250	Approved
0.6765	Remote Similarity	NPD4251	Approved
0.6762	Remote Similarity	NPD6399	Phase 3
0.6754	Remote Similarity	NPD6883	Approved
0.6754	Remote Similarity	NPD7290	Approved
0.6754	Remote Similarity	NPD7102	Approved
0.6735	Remote Similarity	NPD4822	Approved
0.6735	Remote Similarity	NPD4821	Approved
0.6735	Remote Similarity	NPD4819	Approved
0.6735	Remote Similarity	NPD4820	Approved
0.6733	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6731	Remote Similarity	NPD7838	Discovery
0.6729	Remote Similarity	NPD7839	Suspended
0.6727	Remote Similarity	NPD5211	Phase 2
0.6726	Remote Similarity	NPD6011	Approved
0.6726	Remote Similarity	NPD7320	Approved
0.6726	Remote Similarity	NPD6686	Approved
0.6701	Remote Similarity	NPD4268	Approved
0.6701	Remote Similarity	NPD4271	Approved
0.6696	Remote Similarity	NPD6847	Approved
0.6696	Remote Similarity	NPD5739	Approved
0.6696	Remote Similarity	NPD6675	Approved
0.6696	Remote Similarity	NPD7128	Approved
0.6696	Remote Similarity	NPD6402	Approved
0.6696	Remote Similarity	NPD6617	Approved
0.6696	Remote Similarity	NPD6869	Approved
0.6696	Remote Similarity	NPD8130	Phase 1
0.6667	Remote Similarity	NPD6372	Approved
0.6667	Remote Similarity	NPD6373	Approved
0.6667	Remote Similarity	NPD7637	Suspended
0.6638	Remote Similarity	NPD6882	Approved
0.6638	Remote Similarity	NPD8297	Approved
0.6637	Remote Similarity	NPD5701	Approved
0.6607	Remote Similarity	NPD5141	Approved
0.6585	Remote Similarity	NPD7492	Approved
0.6549	Remote Similarity	NPD6008	Approved
0.6545	Remote Similarity	NPD7639	Approved
0.6545	Remote Similarity	NPD4696	Approved
0.6545	Remote Similarity	NPD7640	Approved
0.6545	Remote Similarity	NPD5286	Approved
0.6545	Remote Similarity	NPD5285	Approved
0.6535	Remote Similarity	NPD5331	Approved
0.6535	Remote Similarity	NPD5332	Approved
0.6532	Remote Similarity	NPD6616	Approved
0.6529	Remote Similarity	NPD6054	Approved
0.6529	Remote Similarity	NPD6319	Approved
0.6514	Remote Similarity	NPD6083	Phase 2
0.6514	Remote Similarity	NPD6084	Phase 2
0.6514	Remote Similarity	NPD7902	Approved
0.6509	Remote Similarity	NPD6079	Approved
0.65	Remote Similarity	NPD4790	Discontinued
0.6481	Remote Similarity	NPD5695	Phase 3
0.648	Remote Similarity	NPD7078	Approved
0.6476	Remote Similarity	NPD5370	Suspended
0.6475	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6475	Remote Similarity	NPD8516	Approved
0.6475	Remote Similarity	NPD6016	Approved
0.6475	Remote Similarity	NPD8517	Approved
0.6475	Remote Similarity	NPD6015	Approved
0.6475	Remote Similarity	NPD8515	Approved
0.6475	Remote Similarity	NPD8513	Phase 3
0.6471	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6455	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6455	Remote Similarity	NPD7638	Approved
0.6455	Remote Similarity	NPD5696	Approved
0.6435	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD5224	Approved
0.6429	Remote Similarity	NPD5226	Approved
0.6429	Remote Similarity	NPD7736	Approved
0.6429	Remote Similarity	NPD4633	Approved
0.6429	Remote Similarity	NPD5225	Approved
0.6423	Remote Similarity	NPD5988	Approved
0.6423	Remote Similarity	NPD6370	Approved
0.6422	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6422	Remote Similarity	NPD5222	Approved
0.6422	Remote Similarity	NPD5221	Approved
0.641	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6389	Remote Similarity	NPD7748	Approved
0.6381	Remote Similarity	NPD6903	Approved
0.6372	Remote Similarity	NPD5175	Approved
0.6372	Remote Similarity	NPD5174	Approved
0.6364	Remote Similarity	NPD4755	Approved
0.6364	Remote Similarity	NPD5173	Approved
0.6355	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.6355	Remote Similarity	NPD5281	Approved
0.6355	Remote Similarity	NPD5284	Approved
0.6355	Remote Similarity	NPD7515	Phase 2
0.6346	Remote Similarity	NPD3618	Phase 1
0.6346	Remote Similarity	NPD7334	Approved
0.6346	Remote Similarity	NPD7146	Approved
0.6346	Remote Similarity	NPD6409	Approved
0.6346	Remote Similarity	NPD6684	Approved
0.6346	Remote Similarity	NPD5330	Approved
0.6346	Remote Similarity	NPD7521	Approved
0.6339	Remote Similarity	NPD5344	Discontinued
0.6339	Remote Similarity	NPD5223	Approved
0.6333	Remote Similarity	NPD6274	Approved
0.633	Remote Similarity	NPD5210	Approved
0.633	Remote Similarity	NPD4629	Approved
0.6325	Remote Similarity	NPD4634	Approved
0.6321	Remote Similarity	NPD5328	Approved
0.6311	Remote Similarity	NPD7101	Approved
0.6311	Remote Similarity	NPD7100	Approved
0.6311	Remote Similarity	NPD3666	Approved
0.6311	Remote Similarity	NPD3665	Phase 1
0.6311	Remote Similarity	NPD3133	Approved
0.6303	Remote Similarity	NPD4632	Approved
0.6286	Remote Similarity	NPD3573	Approved
0.6281	Remote Similarity	NPD6317	Approved
0.6275	Remote Similarity	NPD3667	Approved
0.6275	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.6273	Remote Similarity	NPD4697	Phase 3
0.6271	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6262	Remote Similarity	NPD5207	Approved
0.626	Remote Similarity	NPD6059	Approved
0.625	Remote Similarity	NPD7319	Approved
0.625	Remote Similarity	NPD4700	Approved
0.6239	Remote Similarity	NPD7900	Approved
0.6239	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6238	Remote Similarity	NPD4695	Discontinued
0.623	Remote Similarity	NPD6313	Approved
0.623	Remote Similarity	NPD6335	Approved
0.623	Remote Similarity	NPD6314	Approved
0.6226	Remote Similarity	NPD5737	Approved
0.6226	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6226	Remote Similarity	NPD6672	Approved
0.6224	Remote Similarity	NPD8039	Approved
0.622	Remote Similarity	NPD8074	Phase 3
0.622	Remote Similarity	NPD8293	Discontinued
0.6204	Remote Similarity	NPD5693	Phase 1
0.6198	Remote Similarity	NPD6868	Approved
0.619	Remote Similarity	NPD4519	Discontinued
0.619	Remote Similarity	NPD4623	Approved
0.619	Remote Similarity	NPD5279	Phase 3
0.619	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6182	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6168	Remote Similarity	NPD4753	Phase 2
0.6154	Remote Similarity	NPD4729	Approved
0.6154	Remote Similarity	NPD7260	Phase 2
0.6154	Remote Similarity	NPD4786	Approved
0.6154	Remote Similarity	NPD4730	Approved
0.6148	Remote Similarity	NPD6009	Approved
0.6142	Remote Similarity	NPD7507	Approved
0.6111	Remote Similarity	NPD7642	Approved
0.6111	Remote Similarity	NPD8328	Phase 3
0.6106	Remote Similarity	NPD6648	Approved
0.6102	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.61	Remote Similarity	NPD4756	Discovery
0.6095	Remote Similarity	NPD1696	Phase 3
0.6087	Remote Similarity	NPD6647	Phase 2
0.608	Remote Similarity	NPD5983	Phase 2
0.6068	Remote Similarity	NPD6412	Phase 2
0.6064	Remote Similarity	NPD7331	Phase 2
0.605	Remote Similarity	NPD5249	Phase 3
0.605	Remote Similarity	NPD5250	Approved
0.605	Remote Similarity	NPD5251	Approved
0.605	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.605	Remote Similarity	NPD5247	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