NPASS Compound

Structure

NPC287878 OpenBabel07101718242D 28 28 0 0 1 0 0 0 0 0999 V2000 -5.9261 0.9386 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2728 1.5427 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6105 -3.9678 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2968 1.7158 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3091 1.5593 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9508 0.6257 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9631 0.4693 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9890 -0.2091 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9836 -0.3136 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6047 -0.4643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5823 0.7045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3903 -1.2271 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6170 -0.6207 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5878 0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3848 -1.3317 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 -0.9877 0.1564 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3090 -0.9511 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2866 1.7082 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3090 -0.9511 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7916 -2.2452 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0632 2.6450 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.2601 -1.2601 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.7861 -2.3497 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.2038 -3.0542 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.3498 0.9368 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 4 1 0 0 0 0 2 19 1 0 0 0 0 3 27 1 0 0 0 0 4 5 1 0 0 0 0 5 6 1 0 0 0 0 6 7 1 0 0 0 0 7 10 1 0 0 0 0 8 9 1 0 0 0 0 8 11 2 0 0 0 0 9 12 1 0 0 0 0 10 13 2 0 0 0 0 11 14 1 0 0 0 0 12 15 1 0 0 0 0 13 17 1 0 0 0 0 14 20 2 0 0 0 0 15 22 1 0 0 0 0 16 18 2 0 0 0 0 16 21 1 0 0 0 0 18 23 1 0 0 0 0 19 24 2 0 0 0 0 19 28 1 0 0 0 0 20 21 1 0 0 0 0 20 23 1 0 0 0 0 21 25 2 0 0 0 0 22 26 2 0 0 0 0 22 27 1 0 0 0 0 23 17 1 1 0 0 0 23 28 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	388.22
Volume:	423.304
LogP:	3.687
LogD:	3.213
LogS:	-4.367
# Rotatable Bonds:	14
TPSA:	69.67
# H-Bond Aceptor:	5
# H-Bond Donor:	0
# Rings:	1
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.208
Synthetic Accessibility Score:	3.793
Fsp3:	0.522
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.648
MDCK Permeability:	3.1893148843664676e-05
Pgp-inhibitor:	0.935
Pgp-substrate:	0.004
Human Intestinal Absorption (HIA):	0.021
20% Bioavailability (F20%):	0.131
30% Bioavailability (F30%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.971
Plasma Protein Binding (PPB):	95.3108139038086%
Volume Distribution (VD):	1.055
Pgp-substrate:	4.653190612792969%

ADMET: Metabolism

CYP1A2-inhibitor:	0.909
CYP1A2-substrate:	0.36
CYP2C19-inhibitor:	0.793
CYP2C19-substrate:	0.613
CYP2C9-inhibitor:	0.793
CYP2C9-substrate:	0.411
CYP2D6-inhibitor:	0.822
CYP2D6-substrate:	0.053
CYP3A4-inhibitor:	0.932
CYP3A4-substrate:	0.434

ADMET: Excretion

Clearance (CL):	4.548
Half-life (T1/2):	0.853

ADMET: Toxicity

hERG Blockers:	0.212
Human Hepatotoxicity (H-HT):	0.655
Drug-inuced Liver Injury (DILI):	0.311
AMES Toxicity:	0.7
Rat Oral Acute Toxicity:	0.492
Maximum Recommended Daily Dose:	0.836
Skin Sensitization:	0.964
Carcinogencity:	0.899
Eye Corrosion:	0.006
Eye Irritation:	0.016
Respiratory Toxicity:	0.966

Download Data

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

Natural Product: NPC287878

Natural Product ID:	NPC287878
*Common Name:**	Claviridenone E
IUPAC Name:	methyl (E,7E)-7-[(2S)-2-acetyloxy-2-[(Z)-oct-2-enyl]-5-oxocyclopent-3-en-1-ylidene]hept-5-enoate
Synonyms:	4-Deacetoxylclavulone II; Claviridenone E
Standard InCHIKey:	NPTOZTAHJVTRAS-VSHWWUBXSA-N
Standard InCHI:	InChI=1S/C23H32O5/c1-4-5-6-7-10-13-17-23(28-19(2)24)18-16-21(25)20(23)14-11-8-9-12-15-22(26)27-3/h8,10-11,13-14,16,18H,4-7,9,12,15,17H2,1-3H3/b11-8+,13-10-,20-14-/t23-/m0/s1
SMILES:	CCCCC/C=CC[C@@]1(C=CC(=O)/C/1=C/C=C/CCCC(=O)OC)OC(=O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL464519
PubChem CID:	11349752
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0003909] Fatty Acyls [CHEMONTID:0000513] Eicosanoids [CHEMONTID:0001021] Clavulones and derivatives

*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
NPO3077	Clavularia viridis	Species	Clavulariidae	Eukaryota	n.a.	Okinawan	n.a.	PMID[11720524]
NPO3077	Clavularia viridis	Species	Clavulariidae	Eukaryota	n.a.	Formosan soft corals	n.a.	PMID[12444673]
NPO33409	clavularia violacea	Species	Clavulariidae	Eukaryota	n.a.	Formosan soft corals	n.a.	PMID[12444673]
NPO3077	Clavularia viridis	Species	Clavulariidae	Eukaryota	n.a.	Taiwanese octocoral	n.a.	PMID[15104481]
NPO3077	Clavularia viridis	Species	Clavulariidae	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
ED50	3
IC50	2

Activity Type	# Activity
Cell Line	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	ED50	=	4.1	10'-1 ug/ml	PMID[500054]
NPT139	Cell Line	HT-29	Homo sapiens	ED50	=	1.02	ug ml-1	PMID[500054]
NPT168	Cell Line	P388	Mus musculus	ED50	=	1.1	10'-1 ug/ml	PMID[500054]
NPT306	Cell Line	PC-3	Homo sapiens	IC50	=	3500.0	nM	PMID[500055]
NPT139	Cell Line	HT-29	Homo sapiens	IC50	>	10000.0	nM	PMID[500055]

☑ 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 NPC287878 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	1583
0.2-0.3	7998
0.3-0.4	17918
0.4-0.5	9439
0.5-0.6	4196
0.6-0.7	1210
0.7-0.8	154
0.8-0.85	7
0.85-0.9	5
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8873	High Similarity	NPC238948
0.8873	High Similarity	NPC12815
0.8873	High Similarity	NPC215745
0.8514	High Similarity	NPC4492
0.8514	High Similarity	NPC51391
0.8451	Intermediate Similarity	NPC476059
0.8451	Intermediate Similarity	NPC473603
0.8194	Intermediate Similarity	NPC470693
0.8182	Intermediate Similarity	NPC265980
0.8182	Intermediate Similarity	NPC63326
0.8169	Intermediate Similarity	NPC21998
0.8143	Intermediate Similarity	NPC470688
0.8101	Intermediate Similarity	NPC26624
0.8	Intermediate Similarity	NPC16488
0.7917	Intermediate Similarity	NPC203335
0.7887	Intermediate Similarity	NPC220766
0.7857	Intermediate Similarity	NPC155849
0.7808	Intermediate Similarity	NPC470256
0.7778	Intermediate Similarity	NPC191233
0.7763	Intermediate Similarity	NPC474758
0.7714	Intermediate Similarity	NPC151648
0.7711	Intermediate Similarity	NPC315395
0.7711	Intermediate Similarity	NPC291712
0.7711	Intermediate Similarity	NPC316426
0.7703	Intermediate Similarity	NPC476591
0.7703	Intermediate Similarity	NPC88877
0.7671	Intermediate Similarity	NPC194871
0.7662	Intermediate Similarity	NPC260396
0.7606	Intermediate Similarity	NPC474658
0.7606	Intermediate Similarity	NPC322457
0.7595	Intermediate Similarity	NPC253749
0.7595	Intermediate Similarity	NPC279532
0.759	Intermediate Similarity	NPC281172
0.7571	Intermediate Similarity	NPC79756
0.7534	Intermediate Similarity	NPC248125
0.7532	Intermediate Similarity	NPC117746
0.7532	Intermediate Similarity	NPC294434
0.7532	Intermediate Similarity	NPC15499
0.7532	Intermediate Similarity	NPC140287
0.7532	Intermediate Similarity	NPC259599
0.7532	Intermediate Similarity	NPC476355
0.7531	Intermediate Similarity	NPC42470
0.7531	Intermediate Similarity	NPC275507
0.75	Intermediate Similarity	NPC316185
0.75	Intermediate Similarity	NPC473980
0.75	Intermediate Similarity	NPC473981
0.7471	Intermediate Similarity	NPC193396
0.7471	Intermediate Similarity	NPC32944
0.7468	Intermediate Similarity	NPC68156
0.7467	Intermediate Similarity	NPC265574
0.7439	Intermediate Similarity	NPC475690
0.7439	Intermediate Similarity	NPC85772
0.7436	Intermediate Similarity	NPC469414
0.7436	Intermediate Similarity	NPC329826
0.7412	Intermediate Similarity	NPC72513
0.7403	Intermediate Similarity	NPC276336
0.7397	Intermediate Similarity	NPC133904
0.7397	Intermediate Similarity	NPC131174
0.7375	Intermediate Similarity	NPC475699
0.7375	Intermediate Similarity	NPC182292
0.7368	Intermediate Similarity	NPC64234
0.7368	Intermediate Similarity	NPC469660
0.7368	Intermediate Similarity	NPC37929
0.7361	Intermediate Similarity	NPC179087
0.7361	Intermediate Similarity	NPC44343
0.7361	Intermediate Similarity	NPC210303
0.7349	Intermediate Similarity	NPC161045
0.7342	Intermediate Similarity	NPC203277
0.7342	Intermediate Similarity	NPC123360
0.7342	Intermediate Similarity	NPC27205
0.7317	Intermediate Similarity	NPC471325
0.7308	Intermediate Similarity	NPC315843
0.7308	Intermediate Similarity	NPC470686
0.7308	Intermediate Similarity	NPC107654
0.7294	Intermediate Similarity	NPC234038
0.7284	Intermediate Similarity	NPC271632
0.7284	Intermediate Similarity	NPC472965
0.7284	Intermediate Similarity	NPC264227
0.7284	Intermediate Similarity	NPC471299
0.7284	Intermediate Similarity	NPC178277
0.7284	Intermediate Similarity	NPC63649
0.7284	Intermediate Similarity	NPC270126
0.7273	Intermediate Similarity	NPC293114
0.7273	Intermediate Similarity	NPC257618
0.7273	Intermediate Similarity	NPC163003
0.7273	Intermediate Similarity	NPC32552
0.7262	Intermediate Similarity	NPC163615
0.7262	Intermediate Similarity	NPC38569
0.726	Intermediate Similarity	NPC34883
0.725	Intermediate Similarity	NPC180290
0.725	Intermediate Similarity	NPC57744
0.725	Intermediate Similarity	NPC97516
0.7241	Intermediate Similarity	NPC95364
0.7241	Intermediate Similarity	NPC142159
0.7237	Intermediate Similarity	NPC232812
0.7229	Intermediate Similarity	NPC221231
0.7229	Intermediate Similarity	NPC471326
0.7222	Intermediate Similarity	NPC12727
0.7215	Intermediate Similarity	NPC68624
0.7215	Intermediate Similarity	NPC329852
0.7215	Intermediate Similarity	NPC244166
0.7209	Intermediate Similarity	NPC478145
0.7206	Intermediate Similarity	NPC478120
0.7195	Intermediate Similarity	NPC223904
0.7195	Intermediate Similarity	NPC160582
0.7191	Intermediate Similarity	NPC248193
0.7179	Intermediate Similarity	NPC474705
0.7176	Intermediate Similarity	NPC130030
0.7176	Intermediate Similarity	NPC155873
0.7176	Intermediate Similarity	NPC261380
0.7176	Intermediate Similarity	NPC11804
0.7162	Intermediate Similarity	NPC182794
0.716	Intermediate Similarity	NPC128276
0.716	Intermediate Similarity	NPC108816
0.716	Intermediate Similarity	NPC267231
0.716	Intermediate Similarity	NPC99182
0.716	Intermediate Similarity	NPC93763
0.7159	Intermediate Similarity	NPC475879
0.7143	Intermediate Similarity	NPC475989
0.7143	Intermediate Similarity	NPC67183
0.7143	Intermediate Similarity	NPC170377
0.7143	Intermediate Similarity	NPC318766
0.7143	Intermediate Similarity	NPC318468
0.7143	Intermediate Similarity	NPC472017
0.7143	Intermediate Similarity	NPC475947
0.7126	Intermediate Similarity	NPC475902
0.7126	Intermediate Similarity	NPC153570
0.7123	Intermediate Similarity	NPC68110
0.7123	Intermediate Similarity	NPC474774
0.7123	Intermediate Similarity	NPC132243
0.7111	Intermediate Similarity	NPC143210
0.7108	Intermediate Similarity	NPC325031
0.7108	Intermediate Similarity	NPC474980
0.7105	Intermediate Similarity	NPC276290
0.7105	Intermediate Similarity	NPC218477
0.7101	Intermediate Similarity	NPC478117
0.7093	Intermediate Similarity	NPC38576
0.7093	Intermediate Similarity	NPC279859
0.7093	Intermediate Similarity	NPC261721
0.7089	Intermediate Similarity	NPC476590
0.7089	Intermediate Similarity	NPC114727
0.7083	Intermediate Similarity	NPC309408
0.7079	Intermediate Similarity	NPC111114
0.7079	Intermediate Similarity	NPC300312
0.7079	Intermediate Similarity	NPC166110
0.7079	Intermediate Similarity	NPC261607
0.7079	Intermediate Similarity	NPC472705
0.7073	Intermediate Similarity	NPC99651
0.7067	Intermediate Similarity	NPC146811
0.7065	Intermediate Similarity	NPC245521
0.7059	Intermediate Similarity	NPC470918
0.7059	Intermediate Similarity	NPC14575
0.7059	Intermediate Similarity	NPC196487
0.7051	Intermediate Similarity	NPC319163
0.7051	Intermediate Similarity	NPC133098
0.7051	Intermediate Similarity	NPC67076
0.7051	Intermediate Similarity	NPC84038
0.7045	Intermediate Similarity	NPC78008
0.7037	Intermediate Similarity	NPC476028
0.7037	Intermediate Similarity	NPC10572
0.7037	Intermediate Similarity	NPC141789
0.7037	Intermediate Similarity	NPC473825
0.7037	Intermediate Similarity	NPC171204
0.7033	Intermediate Similarity	NPC209355
0.7024	Intermediate Similarity	NPC173609
0.7024	Intermediate Similarity	NPC94200
0.7013	Intermediate Similarity	NPC151481
0.7013	Intermediate Similarity	NPC473277
0.7013	Intermediate Similarity	NPC236208
0.7011	Intermediate Similarity	NPC478144
0.7011	Intermediate Similarity	NPC473248
0.7	Intermediate Similarity	NPC161038
0.7	Intermediate Similarity	NPC29798
0.7	Intermediate Similarity	NPC282644
0.6988	Remote Similarity	NPC281132
0.6977	Remote Similarity	NPC33570
0.6977	Remote Similarity	NPC215364
0.6977	Remote Similarity	NPC197903
0.6977	Remote Similarity	NPC99395
0.6977	Remote Similarity	NPC125290
0.6977	Remote Similarity	NPC470755
0.6977	Remote Similarity	NPC21471
0.6974	Remote Similarity	NPC472266
0.6974	Remote Similarity	NPC225272
0.6966	Remote Similarity	NPC224270
0.6966	Remote Similarity	NPC51653
0.6962	Remote Similarity	NPC58956
0.6962	Remote Similarity	NPC269206
0.6962	Remote Similarity	NPC295633
0.6962	Remote Similarity	NPC222244
0.6962	Remote Similarity	NPC16349
0.6962	Remote Similarity	NPC284006
0.6957	Remote Similarity	NPC473291
0.6951	Remote Similarity	NPC299235
0.6951	Remote Similarity	NPC315765
0.6951	Remote Similarity	NPC474005
0.6944	Remote Similarity	NPC133600
0.6941	Remote Similarity	NPC474976
0.6941	Remote Similarity	NPC474790
0.6941	Remote Similarity	NPC118423

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 NPC287878 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	166
0.1-0.2	1866
0.2-0.3	4299
0.3-0.4	2126
0.4-0.5	550
0.5-0.6	123
0.6-0.7	19
0.7-0.8	1
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
0.8101	Intermediate Similarity	NPD5209	Approved
0.6933	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.679	Remote Similarity	NPD8039	Approved
0.6778	Remote Similarity	NPD5785	Approved
0.6765	Remote Similarity	NPD6927	Phase 3
0.6591	Remote Similarity	NPD5363	Approved
0.6579	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.6489	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6437	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD4756	Discovery
0.6413	Remote Similarity	NPD7838	Discovery
0.6395	Remote Similarity	NPD4252	Approved
0.6364	Remote Similarity	NPD7154	Phase 3
0.6324	Remote Similarity	NPD5343	Approved
0.6322	Remote Similarity	NPD5369	Approved
0.6289	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.625	Remote Similarity	NPD4269	Approved
0.625	Remote Similarity	NPD4270	Approved
0.6222	Remote Similarity	NPD1694	Approved
0.6207	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6184	Remote Similarity	NPD4246	Clinical (unspecified phase)
0.618	Remote Similarity	NPD5362	Discontinued
0.6176	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.617	Remote Similarity	NPD7637	Suspended
0.617	Remote Similarity	NPD7983	Approved
0.6154	Remote Similarity	NPD6371	Approved
0.6154	Remote Similarity	NPD5786	Approved
0.6125	Remote Similarity	NPD4247	Clinical (unspecified phase)
0.6111	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6105	Remote Similarity	NPD5779	Approved
0.6105	Remote Similarity	NPD5778	Approved
0.6064	Remote Similarity	NPD6698	Approved
0.6064	Remote Similarity	NPD46	Approved
0.6044	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.604	Remote Similarity	NPD6647	Phase 2
0.6023	Remote Similarity	NPD4821	Approved
0.6023	Remote Similarity	NPD4820	Approved
0.6023	Remote Similarity	NPD4819	Approved
0.6023	Remote Similarity	NPD4822	Approved
0.6	Remote Similarity	NPD4220	Pre-registration
0.6	Remote Similarity	NPD8779	Phase 3
0.6	Remote Similarity	NPD6108	Clinical (unspecified phase)
0.5977	Remote Similarity	NPD4268	Approved
0.5977	Remote Similarity	NPD4271	Approved
0.5977	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.596	Remote Similarity	NPD4225	Approved
0.5957	Remote Similarity	NPD6101	Approved
0.5957	Remote Similarity	NPD1695	Approved
0.5957	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.5957	Remote Similarity	NPD5370	Suspended
0.5918	Remote Similarity	NPD7839	Suspended
0.59	Remote Similarity	NPD6648	Approved
0.5897	Remote Similarity	NPD4192	Approved
0.5897	Remote Similarity	NPD4191	Approved
0.5897	Remote Similarity	NPD4193	Approved
0.5897	Remote Similarity	NPD4194	Approved
0.5882	Remote Similarity	NPD6097	Approved
0.5882	Remote Similarity	NPD6096	Approved
0.587	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.5843	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.5833	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.5833	Remote Similarity	NPD6411	Approved
0.5833	Remote Similarity	NPD5694	Approved
0.5833	Remote Similarity	NPD6050	Approved
0.5833	Remote Similarity	NPD5693	Phase 1
0.5824	Remote Similarity	NPD5332	Approved
0.5824	Remote Similarity	NPD5331	Approved
0.5818	Remote Similarity	NPD7115	Discovery
0.5802	Remote Similarity	NPD7331	Phase 2
0.5797	Remote Similarity	NPD3174	Discontinued
0.5778	Remote Similarity	NPD4790	Discontinued
0.5745	Remote Similarity	NPD4250	Approved
0.5745	Remote Similarity	NPD4251	Approved
0.5729	Remote Similarity	NPD5692	Phase 3
0.5729	Remote Similarity	NPD5207	Approved
0.5714	Remote Similarity	NPD5282	Discontinued
0.5714	Remote Similarity	NPD6435	Approved
0.5699	Remote Similarity	NPD1696	Phase 3
0.5684	Remote Similarity	NPD5737	Approved
0.5684	Remote Similarity	NPD6672	Approved
0.5648	Remote Similarity	NPD7601	Clinical (unspecified phase)
0.5644	Remote Similarity	NPD7638	Approved
0.5638	Remote Similarity	NPD7334	Approved
0.5638	Remote Similarity	NPD7146	Approved
0.5638	Remote Similarity	NPD5330	Approved
0.5638	Remote Similarity	NPD6409	Approved
0.5638	Remote Similarity	NPD4249	Approved
0.5638	Remote Similarity	NPD7521	Approved
0.5638	Remote Similarity	NPD6684	Approved
0.5632	Remote Similarity	NPD1452	Discontinued
0.5625	Remote Similarity	NPD6080	Approved
0.5625	Remote Similarity	NPD6904	Approved
0.5625	Remote Similarity	NPD6673	Approved
0.5616	Remote Similarity	NPD28	Approved
0.5616	Remote Similarity	NPD29	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