NPASS Compound

Structure

CID37929 OpenBabel06191715372D 22 22 0 0 1 0 0 0 0 0999 V2000 2.0803 -3.8149 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7343 -0.1985 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6810 3.2614 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4445 2.1990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4328 -2.3467 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0817 -3.7626 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2803 -1.0896 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0878 2.3479 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5919 1.2100 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6277 -2.8716 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1724 -2.0329 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7601 0.2788 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2630 -0.3032 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 1.5388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7184 -1.1419 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.5000 1.5388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8090 0.5878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9680 -0.6994 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8090 0.5878 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.9190 -1.0084 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2248 -1.3685 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 6 1 0 0 0 0 2 7 1 0 0 0 0 3 8 1 0 0 0 0 4 9 1 0 0 0 0 5 21 1 0 0 0 0 6 10 1 0 0 0 0 8 16 1 0 0 0 0 10 11 1 0 0 0 0 11 15 1 0 0 0 0 12 17 2 0 0 0 0 12 18 1 0 0 0 0 13 15 1 0 0 0 0 13 19 1 0 0 0 0 14 16 2 0 0 0 0 14 19 1 0 0 0 0 15 7 1 6 0 0 0 16 17 1 0 0 0 0 17 22 1 0 0 0 0 18 20 2 0 0 0 0 18 21 1 0 0 0 0 19 9 1 6 0 0 0 19 22 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	308.24
Volume:	347.085
LogP:	5.067
LogD:	4.751
LogS:	-5.169
# Rotatable Bonds:	10
TPSA:	35.53
# H-Bond Aceptor:	3
# H-Bond Donor:	0
# Rings:	1
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.435
Synthetic Accessibility Score:	4.131
Fsp3:	0.737
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.485
MDCK Permeability:	2.3271948521141894e-05
Pgp-inhibitor:	0.984
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.002
20% Bioavailability (F20%):	0.706
30% Bioavailability (F30%):	0.899

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.262
Plasma Protein Binding (PPB):	95.71468353271484%
Volume Distribution (VD):	1.331
Pgp-substrate:	2.4695358276367188%

ADMET: Metabolism

CYP1A2-inhibitor:	0.929
CYP1A2-substrate:	0.721
CYP2C19-inhibitor:	0.891
CYP2C19-substrate:	0.863
CYP2C9-inhibitor:	0.802
CYP2C9-substrate:	0.049
CYP2D6-inhibitor:	0.906
CYP2D6-substrate:	0.056
CYP3A4-inhibitor:	0.957
CYP3A4-substrate:	0.365

ADMET: Excretion

Clearance (CL):	7.174
Half-life (T1/2):	0.158

ADMET: Toxicity

hERG Blockers:	0.011
Human Hepatotoxicity (H-HT):	0.807
Drug-inuced Liver Injury (DILI):	0.155
AMES Toxicity:	0.019
Rat Oral Acute Toxicity:	0.048
Maximum Recommended Daily Dose:	0.945
Skin Sensitization:	0.897
Carcinogencity:	0.127
Eye Corrosion:	0.021
Eye Irritation:	0.307
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: NPC37929

Natural Product ID:	NPC37929
*Common Name:**	Methyl 2-((R)-3,5-Diethyl-5-((S)-2-Ethylhexyl)Furan-2(5H)-Ylidene)Acetate
IUPAC Name:	methyl (2Z)-2-[(5R)-3,5-diethyl-5-[(2S)-2-ethylhexyl]furan-2-ylidene]acetate
Synonyms:
Standard InCHIKey:	QJKQROHNXPZHBX-DWAAQONKSA-N
Standard InCHI:	InChI=1S/C19H32O3/c1-6-10-11-15(7-2)13-19(9-4)14-16(8-3)17(22-19)12-18(20)21-5/h12,14-15H,6-11,13H2,1-5H3/b17-12-/t15-,19+/m0/s1
SMILES:	CCCC[C@@H](C[C@]1(CC)C=C(/C(=C/C(=O)OC)/O1)CC)CC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2178593
PubChem CID:	10804766
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001983] Dihydrofurans

*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
NPO26409	Plakortis simplex	Species	Plakinidae	Eukaryota	n.a.	Caribbean	n.a.	PMID[10021943]
NPO23381	Echinodorus macrophyllus	Species	Alismataceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10757722]
NPO26409	Plakortis simplex	Species	Plakinidae	Eukaryota	n.a.	Taiwan	n.a.	PMID[11277748]
NPO26409	Plakortis simplex	Species	Plakinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[15921424]
NPO33167	plakinastrella mamillaris	Species	Plakinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[22934537]
NPO26409	Plakortis simplex	Species	Plakinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[23806071]
NPO26409	Plakortis simplex	Species	Plakinidae	Eukaryota	n.a.	China	n.a.	PMID[25115700]
NPO19077	Nyssa sylvatica	Species	Nyssaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26409	Plakortis simplex	Species	Plakinidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23381	Echinodorus macrophyllus	Species	Alismataceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23121	Hedycarya angustifolia	Species	Monimiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6704	Aspergillus navahoensis	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19077	Nyssa sylvatica	Species	Nyssaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7363	Phaedranassa dubia	Species	Amaryllidaceae	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	4

Activity Type	# Activity
Cell Line	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT181	Cell Line	Bel-7402	Homo sapiens	IC50	>	100000.0	nM	PMID[492818]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	100000.0	nM	PMID[492818]
NPT111	Cell Line	K562	Homo sapiens	IC50	=	5300.0	nM	PMID[492818]
NPT165	Cell Line	HeLa	Homo sapiens	IC50	=	4200.0	nM	PMID[492818]

☑ 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 NPC37929 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	186
0.1-0.2	1365
0.2-0.3	6474
0.3-0.4	18378
0.4-0.5	10013
0.5-0.6	4787
0.6-0.7	1288
0.7-0.8	196
0.8-0.85	3
0.85-0.9	2
0.9-0.95	2
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC64234
0.9846	High Similarity	NPC232812
0.9091	High Similarity	NPC191233
0.8955	High Similarity	NPC472266
0.8939	High Similarity	NPC220766
0.8696	High Similarity	NPC470693
0.8429	Intermediate Similarity	NPC265574
0.831	Intermediate Similarity	NPC316029
0.8286	Intermediate Similarity	NPC276290
0.8219	Intermediate Similarity	NPC470686
0.8133	Intermediate Similarity	NPC54996
0.8056	Intermediate Similarity	NPC315285
0.8028	Intermediate Similarity	NPC313444
0.7973	Intermediate Similarity	NPC474758
0.7917	Intermediate Similarity	NPC269841
0.7895	Intermediate Similarity	NPC315394
0.7895	Intermediate Similarity	NPC471225
0.7857	Intermediate Similarity	NPC470688
0.7826	Intermediate Similarity	NPC217940
0.7826	Intermediate Similarity	NPC155849
0.7808	Intermediate Similarity	NPC315597
0.7808	Intermediate Similarity	NPC469660
0.7792	Intermediate Similarity	NPC474005
0.7763	Intermediate Similarity	NPC301525
0.7727	Intermediate Similarity	NPC96663
0.7711	Intermediate Similarity	NPC260343
0.7703	Intermediate Similarity	NPC477084
0.7703	Intermediate Similarity	NPC181587
0.7671	Intermediate Similarity	NPC101622
0.7662	Intermediate Similarity	NPC316324
0.7662	Intermediate Similarity	NPC180290
0.7662	Intermediate Similarity	NPC473825
0.7632	Intermediate Similarity	NPC329826
0.7632	Intermediate Similarity	NPC469414
0.7632	Intermediate Similarity	NPC329852
0.7619	Intermediate Similarity	NPC64913
0.7619	Intermediate Similarity	NPC242877
0.76	Intermediate Similarity	NPC222244
0.76	Intermediate Similarity	NPC16349
0.7568	Intermediate Similarity	NPC4299
0.7564	Intermediate Similarity	NPC128276
0.7564	Intermediate Similarity	NPC471220
0.7558	Intermediate Similarity	NPC248193
0.7536	Intermediate Similarity	NPC127824
0.7532	Intermediate Similarity	NPC469880
0.7531	Intermediate Similarity	NPC475714
0.7531	Intermediate Similarity	NPC170377
0.75	Intermediate Similarity	NPC259599
0.75	Intermediate Similarity	NPC116013
0.75	Intermediate Similarity	NPC294434
0.75	Intermediate Similarity	NPC117746
0.75	Intermediate Similarity	NPC472302
0.75	Intermediate Similarity	NPC471325
0.75	Intermediate Similarity	NPC42470
0.75	Intermediate Similarity	NPC15499
0.75	Intermediate Similarity	NPC315115
0.75	Intermediate Similarity	NPC471956
0.7468	Intermediate Similarity	NPC471537
0.7467	Intermediate Similarity	NPC257618
0.7465	Intermediate Similarity	NPC34883
0.7442	Intermediate Similarity	NPC166110
0.7442	Intermediate Similarity	NPC175842
0.7442	Intermediate Similarity	NPC32494
0.7439	Intermediate Similarity	NPC475706
0.7436	Intermediate Similarity	NPC57744
0.7436	Intermediate Similarity	NPC68156
0.7436	Intermediate Similarity	NPC476439
0.7432	Intermediate Similarity	NPC329656
0.7432	Intermediate Similarity	NPC475004
0.7407	Intermediate Similarity	NPC221231
0.7407	Intermediate Similarity	NPC474028
0.7407	Intermediate Similarity	NPC471218
0.7407	Intermediate Similarity	NPC471326
0.7407	Intermediate Similarity	NPC35556
0.7407	Intermediate Similarity	NPC474439
0.7403	Intermediate Similarity	NPC244166
0.7397	Intermediate Similarity	NPC21998
0.7391	Intermediate Similarity	NPC143810
0.7391	Intermediate Similarity	NPC83838
0.7375	Intermediate Similarity	NPC268827
0.7368	Intermediate Similarity	NPC476490
0.7368	Intermediate Similarity	NPC476489
0.7368	Intermediate Similarity	NPC287878
0.7361	Intermediate Similarity	NPC182794
0.7356	Intermediate Similarity	NPC59646
0.7349	Intermediate Similarity	NPC472442
0.7349	Intermediate Similarity	NPC197903
0.7349	Intermediate Similarity	NPC471185
0.7349	Intermediate Similarity	NPC99395
0.7342	Intermediate Similarity	NPC299235
0.7342	Intermediate Similarity	NPC184737
0.7342	Intermediate Similarity	NPC315765
0.7333	Intermediate Similarity	NPC475310
0.7333	Intermediate Similarity	NPC67183
0.7326	Intermediate Similarity	NPC3436
0.7324	Intermediate Similarity	NPC179087
0.7324	Intermediate Similarity	NPC210303
0.7324	Intermediate Similarity	NPC44343
0.7317	Intermediate Similarity	NPC474809
0.7317	Intermediate Similarity	NPC12283
0.7317	Intermediate Similarity	NPC475947
0.7317	Intermediate Similarity	NPC30502
0.7317	Intermediate Similarity	NPC474193
0.7308	Intermediate Similarity	NPC27205
0.7308	Intermediate Similarity	NPC476317
0.7308	Intermediate Similarity	NPC123360
0.7297	Intermediate Similarity	NPC218477
0.7297	Intermediate Similarity	NPC474823
0.7294	Intermediate Similarity	NPC473658
0.7284	Intermediate Similarity	NPC184208
0.7284	Intermediate Similarity	NPC475944
0.7284	Intermediate Similarity	NPC325031
0.7284	Intermediate Similarity	NPC474894
0.7284	Intermediate Similarity	NPC315731
0.7284	Intermediate Similarity	NPC8538
0.7284	Intermediate Similarity	NPC112868
0.7273	Intermediate Similarity	NPC470521
0.7273	Intermediate Similarity	NPC140287
0.7273	Intermediate Similarity	NPC476355
0.7273	Intermediate Similarity	NPC477204
0.725	Intermediate Similarity	NPC271632
0.725	Intermediate Similarity	NPC63649
0.725	Intermediate Similarity	NPC472965
0.725	Intermediate Similarity	NPC178277
0.725	Intermediate Similarity	NPC469690
0.725	Intermediate Similarity	NPC264227
0.7241	Intermediate Similarity	NPC470520
0.7237	Intermediate Similarity	NPC472254
0.7237	Intermediate Similarity	NPC84038
0.7237	Intermediate Similarity	NPC5734
0.7237	Intermediate Similarity	NPC163003
0.7229	Intermediate Similarity	NPC14575
0.7229	Intermediate Similarity	NPC96055
0.7229	Intermediate Similarity	NPC471302
0.7229	Intermediate Similarity	NPC318515
0.7229	Intermediate Similarity	NPC196487
0.7229	Intermediate Similarity	NPC471301
0.7222	Intermediate Similarity	NPC226066
0.7222	Intermediate Similarity	NPC477457
0.7222	Intermediate Similarity	NPC477456
0.7215	Intermediate Similarity	NPC187568
0.7215	Intermediate Similarity	NPC189206
0.7215	Intermediate Similarity	NPC262747
0.7215	Intermediate Similarity	NPC41780
0.7215	Intermediate Similarity	NPC84360
0.7209	Intermediate Similarity	NPC225283
0.7209	Intermediate Similarity	NPC95364
0.7209	Intermediate Similarity	NPC307092
0.7209	Intermediate Similarity	NPC142159
0.7195	Intermediate Similarity	NPC123908
0.7195	Intermediate Similarity	NPC10080
0.7195	Intermediate Similarity	NPC471298
0.7195	Intermediate Similarity	NPC173609
0.7179	Intermediate Similarity	NPC228978
0.7176	Intermediate Similarity	NPC478145
0.7176	Intermediate Similarity	NPC191283
0.7176	Intermediate Similarity	NPC125925
0.716	Intermediate Similarity	NPC474510
0.7159	Intermediate Similarity	NPC1108
0.7143	Intermediate Similarity	NPC474424
0.7143	Intermediate Similarity	NPC471223
0.7143	Intermediate Similarity	NPC474705
0.7143	Intermediate Similarity	NPC474013
0.7143	Intermediate Similarity	NPC133600
0.7143	Intermediate Similarity	NPC67081
0.7143	Intermediate Similarity	NPC477085
0.7143	Intermediate Similarity	NPC278673
0.7125	Intermediate Similarity	NPC474816
0.7125	Intermediate Similarity	NPC209135
0.7123	Intermediate Similarity	NPC471556
0.7111	Intermediate Similarity	NPC16967
0.7111	Intermediate Similarity	NPC301596
0.7111	Intermediate Similarity	NPC299396
0.7111	Intermediate Similarity	NPC172998
0.7108	Intermediate Similarity	NPC288281
0.7108	Intermediate Similarity	NPC472440
0.7108	Intermediate Similarity	NPC311070
0.7108	Intermediate Similarity	NPC477124
0.7108	Intermediate Similarity	NPC471297
0.7108	Intermediate Similarity	NPC193198
0.7108	Intermediate Similarity	NPC475989
0.7105	Intermediate Similarity	NPC329904
0.7105	Intermediate Similarity	NPC473361
0.7093	Intermediate Similarity	NPC26078
0.7093	Intermediate Similarity	NPC93411
0.7093	Intermediate Similarity	NPC475739
0.7093	Intermediate Similarity	NPC106332
0.7089	Intermediate Similarity	NPC473223
0.7089	Intermediate Similarity	NPC477202
0.7089	Intermediate Similarity	NPC235906
0.7089	Intermediate Similarity	NPC4509
0.7073	Intermediate Similarity	NPC59994
0.7073	Intermediate Similarity	NPC141810
0.7073	Intermediate Similarity	NPC78677
0.7067	Intermediate Similarity	NPC470256
0.7067	Intermediate Similarity	NPC310210
0.7059	Intermediate Similarity	NPC164393
0.7059	Intermediate Similarity	NPC291712
0.7059	Intermediate Similarity	NPC61527
0.7059	Intermediate Similarity	NPC234038

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 NPC37929 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	178
0.1-0.2	1734
0.2-0.3	4117
0.3-0.4	2319
0.4-0.5	628
0.5-0.6	156
0.6-0.7	15
0.7-0.8	3
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
0.8116	Intermediate Similarity	NPD2685	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD5325	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD8039	Approved
0.6988	Remote Similarity	NPD5209	Approved
0.6988	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6742	Remote Similarity	NPD7838	Discovery
0.6706	Remote Similarity	NPD7154	Phase 3
0.6628	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6486	Remote Similarity	NPD4191	Approved
0.6486	Remote Similarity	NPD4194	Approved
0.6486	Remote Similarity	NPD4193	Approved
0.6486	Remote Similarity	NPD4192	Approved
0.6471	Remote Similarity	NPD6927	Phase 3
0.6444	Remote Similarity	NPD6051	Approved
0.6421	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6386	Remote Similarity	NPD4756	Discovery
0.6374	Remote Similarity	NPD6698	Approved
0.6374	Remote Similarity	NPD46	Approved
0.6364	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD1694	Approved
0.6354	Remote Similarity	NPD6648	Approved
0.6196	Remote Similarity	NPD5785	Approved
0.6163	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6163	Remote Similarity	NPD4821	Approved
0.6163	Remote Similarity	NPD4822	Approved
0.6163	Remote Similarity	NPD4820	Approved
0.6163	Remote Similarity	NPD4819	Approved
0.6154	Remote Similarity	NPD7331	Phase 2
0.6136	Remote Similarity	NPD5362	Discontinued
0.6129	Remote Similarity	NPD6050	Approved
0.6129	Remote Similarity	NPD5693	Phase 1
0.6111	Remote Similarity	NPD6409	Approved
0.6111	Remote Similarity	NPD7146	Approved
0.6111	Remote Similarity	NPD7334	Approved
0.6111	Remote Similarity	NPD6684	Approved
0.6111	Remote Similarity	NPD5330	Approved
0.6111	Remote Similarity	NPD7521	Approved
0.6087	Remote Similarity	NPD1695	Approved
0.6082	Remote Similarity	NPD7638	Approved
0.6044	Remote Similarity	NPD4251	Approved
0.6044	Remote Similarity	NPD4250	Approved
0.6022	Remote Similarity	NPD5692	Phase 3
0.6022	Remote Similarity	NPD5207	Approved
0.602	Remote Similarity	NPD7639	Approved
0.602	Remote Similarity	NPD7640	Approved
0.6	Remote Similarity	NPD5363	Approved
0.5978	Remote Similarity	NPD6903	Approved
0.5978	Remote Similarity	NPD6672	Approved
0.5978	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.5978	Remote Similarity	NPD5737	Approved
0.5962	Remote Similarity	NPD2067	Discontinued
0.596	Remote Similarity	NPD5344	Discontinued
0.5957	Remote Similarity	NPD5694	Approved
0.5957	Remote Similarity	NPD7637	Suspended
0.5957	Remote Similarity	NPD7983	Approved
0.5955	Remote Similarity	NPD5332	Approved
0.5955	Remote Similarity	NPD5331	Approved
0.5949	Remote Similarity	NPD6108	Clinical (unspecified phase)
0.5942	Remote Similarity	NPD4220	Pre-registration
0.5941	Remote Similarity	NPD5909	Discontinued
0.5934	Remote Similarity	NPD4249	Approved
0.593	Remote Similarity	NPD4271	Approved
0.593	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.593	Remote Similarity	NPD4268	Approved
0.5921	Remote Similarity	NPD4246	Clinical (unspecified phase)
0.5918	Remote Similarity	NPD4225	Approved
0.5914	Remote Similarity	NPD6080	Approved
0.5914	Remote Similarity	NPD6673	Approved
0.5914	Remote Similarity	NPD6904	Approved
0.5909	Remote Similarity	NPD4790	Discontinued
0.5909	Remote Similarity	NPD5369	Approved
0.5895	Remote Similarity	NPD5779	Approved
0.5895	Remote Similarity	NPD5778	Approved
0.5849	Remote Similarity	NPD6053	Discontinued
0.5843	Remote Similarity	NPD6435	Approved
0.5843	Remote Similarity	NPD4270	Approved
0.5843	Remote Similarity	NPD4269	Approved
0.5833	Remote Similarity	NPD6924	Approved
0.5833	Remote Similarity	NPD6926	Approved
0.5825	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.5823	Remote Similarity	NPD7341	Phase 2
0.5806	Remote Similarity	NPD5208	Approved
0.5778	Remote Similarity	NPD6695	Phase 3
0.5775	Remote Similarity	NPD29	Approved
0.5775	Remote Similarity	NPD28	Approved
0.5773	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.5773	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.5769	Remote Similarity	NPD6686	Approved
0.5761	Remote Similarity	NPD6098	Approved
0.5761	Remote Similarity	NPD5786	Approved
0.5758	Remote Similarity	NPD5926	Approved
0.5747	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.5745	Remote Similarity	NPD6101	Approved
0.5745	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD1145	Discontinued
0.5714	Remote Similarity	NPD7839	Suspended
0.5714	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD7503	Approved
0.5699	Remote Similarity	NPD3573	Approved
0.5699	Remote Similarity	NPD1282	Approved
0.5698	Remote Similarity	NPD6933	Approved
0.5686	Remote Similarity	NPD6647	Phase 2
0.566	Remote Similarity	NPD6371	Approved
0.5657	Remote Similarity	NPD6083	Phase 2
0.5657	Remote Similarity	NPD6084	Phase 2
0.5641	Remote Similarity	NPD368	Approved
0.5636	Remote Similarity	NPD7505	Discontinued
0.5625	Remote Similarity	NPD5284	Approved
0.5625	Remote Similarity	NPD5281	Approved
0.5625	Remote Similarity	NPD6411	Approved
0.5618	Remote Similarity	NPD5368	Approved
0.5618	Remote Similarity	NPD7332	Phase 2
0.5618	Remote Similarity	NPD6931	Approved
0.5618	Remote Similarity	NPD7514	Phase 3
0.5618	Remote Similarity	NPD6930	Phase 2
0.5618	Remote Similarity	NPD4252	Approved
0.5612	Remote Similarity	NPD5695	Phase 3
0.5612	Remote Similarity	NPD5654	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