NPASS Compound

Structure

NPC469806 OpenBabel07101718242D 26 28 0 0 1 0 0 0 0 0999 V2000 -0.5909 -2.0032 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1653 -4.3212 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4067 -0.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5472 -2.4190 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2382 -1.4680 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5254 -2.6270 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9511 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2601 -1.2601 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8344 -3.5780 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5981 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.5388 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9511 -0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8126 -3.7859 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 3.4641 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5388 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1216 -4.7370 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.4817 -3.0428 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 13 1 0 0 0 0 2 14 1 0 0 0 0 4 5 2 0 0 0 0 4 6 1 0 0 0 0 5 13 1 0 0 0 0 6 14 2 0 0 0 0 7 8 1 0 0 0 0 7 16 1 0 0 0 0 9 10 1 0 0 0 0 10 22 1 0 0 0 0 11 15 1 0 0 0 0 11 16 1 0 0 0 0 12 18 1 0 0 0 0 12 19 1 0 0 0 0 13 20 2 0 0 0 0 14 21 1 0 0 0 0 15 9 1 6 0 0 0 15 17 1 0 0 0 0 16 23 2 0 0 0 0 17 8 1 1 0 0 0 17 18 1 0 0 0 0 18 22 1 1 0 0 0 19 20 1 0 0 0 0 19 24 2 0 0 0 0 20 22 1 0 0 0 0 21 25 2 0 0 0 0 21 26 1 0 0 0 0 22 3 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	356.2
Volume:	382.741
LogP:	3.072
LogD:	2.565
LogS:	-3.786
# Rotatable Bonds:	3
TPSA:	71.44
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.606
Synthetic Accessibility Score:	4.431
Fsp3:	0.591
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.163
MDCK Permeability:	2.507458884792868e-05
Pgp-inhibitor:	0.661
Pgp-substrate:	0.238
Human Intestinal Absorption (HIA):	0.025
20% Bioavailability (F20%):	0.004
30% Bioavailability (F30%):	0.004

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.519
Plasma Protein Binding (PPB):	89.8355484008789%
Volume Distribution (VD):	0.369
Pgp-substrate:	10.66164779663086%

ADMET: Metabolism

CYP1A2-inhibitor:	0.083
CYP1A2-substrate:	0.693
CYP2C19-inhibitor:	0.103
CYP2C19-substrate:	0.335
CYP2C9-inhibitor:	0.304
CYP2C9-substrate:	0.562
CYP2D6-inhibitor:	0.037
CYP2D6-substrate:	0.27
CYP3A4-inhibitor:	0.105
CYP3A4-substrate:	0.241

ADMET: Excretion

Clearance (CL):	2.428
Half-life (T1/2):	0.827

ADMET: Toxicity

hERG Blockers:	0.072
Human Hepatotoxicity (H-HT):	0.254
Drug-inuced Liver Injury (DILI):	0.448
AMES Toxicity:	0.616
Rat Oral Acute Toxicity:	0.389
Maximum Recommended Daily Dose:	0.904
Skin Sensitization:	0.937
Carcinogencity:	0.914
Eye Corrosion:	0.004
Eye Irritation:	0.04
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: NPC469806

Natural Product ID:	NPC469806
*Common Name:**	Jaspolide F
IUPAC Name:	(2E,4E,6Z)-6-[(3aS,5aS,9aS,9bS)-3a-methyl-2,7-dioxo-4,5,5a,6,8,9,9a,9b-octahydro-1H-cyclopenta[a]naphthalen-3-ylidene]-2-methylhepta-2,4-dienoic acid
Synonyms:	Jaspolide F
Standard InCHIKey:	VPELENZNBAVUTK-KVUMNOJHSA-N
Standard InCHI:	InChI=1S/C22H28O4/c1-13(5-4-6-14(2)21(25)26)20-19(24)12-18-17-8-7-16(23)11-15(17)9-10-22(18,20)3/h4-6,15,17-18H,7-12H2,1-3H3,(H,25,26)/b5-4+,14-6+,20-13+/t15-,17-,18-,22-/m0/s1
SMILES:	O=C1CC[C@H]2[C@H](C1)CC[C@]1([C@H]2CC(=O)/C/1=C(C=CC=C(C(=O)O)/C)/C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1173687
PubChem CID:	49799484
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001550] Sesquiterpenoids

*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
NPO28502	Rhabdastrella globostellata	Species	Ancorinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[11858759]
NPO28502	Rhabdastrella globostellata	Species	Ancorinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[16499318]
NPO28502	Rhabdastrella globostellata	Species	Ancorinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[16562838]
NPO28502	Rhabdastrella globostellata	Species	Ancorinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[17524651]
NPO28502	Rhabdastrella globostellata	Species	Ancorinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[20627740]
NPO28502	Rhabdastrella globostellata	Species	Ancorinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[20718449]
NPO28502	Rhabdastrella globostellata	Species	Ancorinidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	5

Activity Type	# Activity
Cell Line	4
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT179	Cell Line	A2780	Homo sapiens	IC50	=	7920.0	nM	PMID[533639]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	50000.0	nM	PMID[533639]
NPT181	Cell Line	Bel-7402	Homo sapiens	IC50	>	50000.0	nM	PMID[533639]
NPT180	Cell Line	HCT-8	Homo sapiens	IC50	>	50000.0	nM	PMID[533639]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	50000.0	nM	PMID[533639]

☑ 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 NPC469806 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	139
0.1-0.2	987
0.2-0.3	5305
0.3-0.4	14944
0.4-0.5	9384
0.5-0.6	7571
0.6-0.7	3593
0.7-0.8	677
0.8-0.85	62
0.85-0.9	18
0.9-0.95	9
0.95-1	8

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC469799
0.987	High Similarity	NPC279639
0.987	High Similarity	NPC3856
0.974	High Similarity	NPC469805
0.974	High Similarity	NPC469804
0.9737	High Similarity	NPC469798
0.9737	High Similarity	NPC469797
0.9146	High Similarity	NPC476293
0.9079	High Similarity	NPC469803
0.9012	High Similarity	NPC87552
0.9	High Similarity	NPC472239
0.8941	High Similarity	NPC473986
0.8941	High Similarity	NPC474018
0.8902	High Similarity	NPC60350
0.8889	High Similarity	NPC474790
0.8889	High Similarity	NPC474976
0.8831	High Similarity	NPC476346
0.878	High Similarity	NPC178025
0.878	High Similarity	NPC181743
0.878	High Similarity	NPC16287
0.8765	High Similarity	NPC472867
0.8765	High Similarity	NPC142253
0.8765	High Similarity	NPC3511
0.8701	High Similarity	NPC329866
0.8701	High Similarity	NPC474797
0.8701	High Similarity	NPC474796
0.8684	High Similarity	NPC133253
0.8684	High Similarity	NPC21944
0.8675	High Similarity	NPC8571
0.8571	High Similarity	NPC56747
0.8571	High Similarity	NPC130016
0.8571	High Similarity	NPC180015
0.8571	High Similarity	NPC109576
0.8539	High Similarity	NPC301534
0.8539	High Similarity	NPC250757
0.8506	High Similarity	NPC204341
0.8488	Intermediate Similarity	NPC262043
0.8471	Intermediate Similarity	NPC163016
0.8471	Intermediate Similarity	NPC75315
0.8471	Intermediate Similarity	NPC236618
0.8434	Intermediate Similarity	NPC97913
0.8372	Intermediate Similarity	NPC117122
0.8353	Intermediate Similarity	NPC472869
0.8353	Intermediate Similarity	NPC186975
0.8333	Intermediate Similarity	NPC19849
0.8333	Intermediate Similarity	NPC248758
0.8333	Intermediate Similarity	NPC164577
0.8333	Intermediate Similarity	NPC472864
0.8295	Intermediate Similarity	NPC23217
0.8276	Intermediate Similarity	NPC474844
0.8276	Intermediate Similarity	NPC66344
0.8272	Intermediate Similarity	NPC198240
0.8256	Intermediate Similarity	NPC136948
0.825	Intermediate Similarity	NPC469793
0.825	Intermediate Similarity	NPC469796
0.8235	Intermediate Similarity	NPC29447
0.8235	Intermediate Similarity	NPC269638
0.8205	Intermediate Similarity	NPC54123
0.8172	Intermediate Similarity	NPC282524
0.8161	Intermediate Similarity	NPC472870
0.8161	Intermediate Similarity	NPC72397
0.8152	Intermediate Similarity	NPC108368
0.8152	Intermediate Similarity	NPC57079
0.8148	Intermediate Similarity	NPC61952
0.8148	Intermediate Similarity	NPC91665
0.8118	Intermediate Similarity	NPC472865
0.8111	Intermediate Similarity	NPC299100
0.8095	Intermediate Similarity	NPC320514
0.8095	Intermediate Similarity	NPC94200
0.8077	Intermediate Similarity	NPC251929
0.8077	Intermediate Similarity	NPC2634
0.8077	Intermediate Similarity	NPC265782
0.8068	Intermediate Similarity	NPC36668
0.8068	Intermediate Similarity	NPC118011
0.8065	Intermediate Similarity	NPC266955
0.8046	Intermediate Similarity	NPC128644
0.8025	Intermediate Similarity	NPC19907
0.8025	Intermediate Similarity	NPC180886
0.8022	Intermediate Similarity	NPC476174
0.8022	Intermediate Similarity	NPC180950
0.8022	Intermediate Similarity	NPC171395
0.8	Intermediate Similarity	NPC49019
0.8	Intermediate Similarity	NPC20025
0.8	Intermediate Similarity	NPC469939
0.8	Intermediate Similarity	NPC72151
0.8	Intermediate Similarity	NPC118423
0.8	Intermediate Similarity	NPC242069
0.7979	Intermediate Similarity	NPC115899
0.7978	Intermediate Similarity	NPC472866
0.7976	Intermediate Similarity	NPC477372
0.7976	Intermediate Similarity	NPC278459
0.7976	Intermediate Similarity	NPC4166
0.7957	Intermediate Similarity	NPC166745
0.7957	Intermediate Similarity	NPC235464
0.7955	Intermediate Similarity	NPC48107
0.7949	Intermediate Similarity	NPC139397
0.7935	Intermediate Similarity	NPC29152
0.7931	Intermediate Similarity	NPC168248
0.7931	Intermediate Similarity	NPC6247
0.7927	Intermediate Similarity	NPC97377
0.7912	Intermediate Similarity	NPC474690
0.7901	Intermediate Similarity	NPC473171
0.7895	Intermediate Similarity	NPC320447
0.7889	Intermediate Similarity	NPC470113
0.7882	Intermediate Similarity	NPC268122
0.7882	Intermediate Similarity	NPC311092
0.7875	Intermediate Similarity	NPC251705
0.7875	Intermediate Similarity	NPC474228
0.7875	Intermediate Similarity	NPC303613
0.7849	Intermediate Similarity	NPC156546
0.7848	Intermediate Similarity	NPC260040
0.7848	Intermediate Similarity	NPC307176
0.7841	Intermediate Similarity	NPC476409
0.7831	Intermediate Similarity	NPC74410
0.7831	Intermediate Similarity	NPC169095
0.7826	Intermediate Similarity	NPC209355
0.7826	Intermediate Similarity	NPC293052
0.7826	Intermediate Similarity	NPC88310
0.7816	Intermediate Similarity	NPC142649
0.7816	Intermediate Similarity	NPC472940
0.7816	Intermediate Similarity	NPC472931
0.7816	Intermediate Similarity	NPC11711
0.7812	Intermediate Similarity	NPC475050
0.7805	Intermediate Similarity	NPC69408
0.7802	Intermediate Similarity	NPC472871
0.7792	Intermediate Similarity	NPC255781
0.7792	Intermediate Similarity	NPC81907
0.7791	Intermediate Similarity	NPC41539
0.7791	Intermediate Similarity	NPC470015
0.7791	Intermediate Similarity	NPC102197
0.7791	Intermediate Similarity	NPC168188
0.7791	Intermediate Similarity	NPC310470
0.7791	Intermediate Similarity	NPC69279
0.7791	Intermediate Similarity	NPC83569
0.7789	Intermediate Similarity	NPC99411
0.7778	Intermediate Similarity	NPC475965
0.7778	Intermediate Similarity	NPC474842
0.7778	Intermediate Similarity	NPC309852
0.7778	Intermediate Similarity	NPC3753
0.7778	Intermediate Similarity	NPC237591
0.7765	Intermediate Similarity	NPC147066
0.7765	Intermediate Similarity	NPC90055
0.775	Intermediate Similarity	NPC470078
0.775	Intermediate Similarity	NPC305501
0.775	Intermediate Similarity	NPC115023
0.775	Intermediate Similarity	NPC234707
0.7742	Intermediate Similarity	NPC472941
0.7742	Intermediate Similarity	NPC456
0.7742	Intermediate Similarity	NPC471153
0.7738	Intermediate Similarity	NPC190211
0.7738	Intermediate Similarity	NPC477371
0.7711	Intermediate Similarity	NPC165711
0.7708	Intermediate Similarity	NPC114540
0.7708	Intermediate Similarity	NPC155332
0.7708	Intermediate Similarity	NPC32577
0.7692	Intermediate Similarity	NPC476187
0.7684	Intermediate Similarity	NPC35751
0.7683	Intermediate Similarity	NPC476844
0.7683	Intermediate Similarity	NPC169056
0.7683	Intermediate Similarity	NPC225665
0.7683	Intermediate Similarity	NPC476795
0.7683	Intermediate Similarity	NPC293803
0.7683	Intermediate Similarity	NPC255650
0.7683	Intermediate Similarity	NPC65650
0.7683	Intermediate Similarity	NPC166018
0.7674	Intermediate Similarity	NPC133391
0.7674	Intermediate Similarity	NPC302661
0.7674	Intermediate Similarity	NPC238991
0.7667	Intermediate Similarity	NPC214387
0.7667	Intermediate Similarity	NPC5509
0.7662	Intermediate Similarity	NPC107258
0.766	Intermediate Similarity	NPC474785
0.766	Intermediate Similarity	NPC208094
0.766	Intermediate Similarity	NPC474938
0.766	Intermediate Similarity	NPC253826
0.7654	Intermediate Similarity	NPC470045
0.7654	Intermediate Similarity	NPC470044
0.7654	Intermediate Similarity	NPC321017
0.7653	Intermediate Similarity	NPC266570
0.7653	Intermediate Similarity	NPC189863
0.764	Intermediate Similarity	NPC141292
0.764	Intermediate Similarity	NPC181327
0.7634	Intermediate Similarity	NPC295347
0.7629	Intermediate Similarity	NPC473283
0.7629	Intermediate Similarity	NPC329345
0.7629	Intermediate Similarity	NPC475526
0.7625	Intermediate Similarity	NPC282593
0.7625	Intermediate Similarity	NPC35734
0.7625	Intermediate Similarity	NPC159577
0.7619	Intermediate Similarity	NPC179028
0.7619	Intermediate Similarity	NPC275494
0.7619	Intermediate Similarity	NPC471409
0.7619	Intermediate Similarity	NPC189485
0.7619	Intermediate Similarity	NPC82635
0.7619	Intermediate Similarity	NPC105197
0.7614	Intermediate Similarity	NPC311702
0.7614	Intermediate Similarity	NPC94531
0.7614	Intermediate Similarity	NPC65661
0.7614	Intermediate Similarity	NPC476426
0.7614	Intermediate Similarity	NPC123319

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 NPC469806 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	139
0.1-0.2	1158
0.2-0.3	3957
0.3-0.4	2758
0.4-0.5	661
0.5-0.6	222
0.6-0.7	181
0.7-0.8	71
0.8-0.85	2
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8462	Intermediate Similarity	NPD4058	Approved
0.8077	Intermediate Similarity	NPD4691	Approved
0.8	Intermediate Similarity	NPD4687	Approved
0.7949	Intermediate Similarity	NPD4137	Phase 3
0.7889	Intermediate Similarity	NPD5284	Approved
0.7889	Intermediate Similarity	NPD5281	Approved
0.7848	Intermediate Similarity	NPD4747	Approved
0.7778	Intermediate Similarity	NPD5733	Approved
0.775	Intermediate Similarity	NPD5276	Approved
0.7528	Intermediate Similarity	NPD4623	Approved
0.7528	Intermediate Similarity	NPD4519	Discontinued
0.7471	Intermediate Similarity	NPD4221	Approved
0.7471	Intermediate Similarity	NPD4223	Phase 3
0.7412	Intermediate Similarity	NPD5784	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD3527	Clinical (unspecified phase)
0.7375	Intermediate Similarity	NPD3621	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD4694	Approved
0.7333	Intermediate Similarity	NPD5690	Phase 2
0.7333	Intermediate Similarity	NPD5280	Approved
0.732	Intermediate Similarity	NPD6404	Discontinued
0.7312	Intermediate Similarity	NPD5694	Approved
0.7303	Intermediate Similarity	NPD3666	Approved
0.7303	Intermediate Similarity	NPD3665	Phase 1
0.7303	Intermediate Similarity	NPD3133	Approved
0.7303	Intermediate Similarity	NPD4197	Approved
0.7283	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD4191	Approved
0.7273	Intermediate Similarity	NPD4192	Approved
0.7273	Intermediate Similarity	NPD4193	Approved
0.7273	Intermediate Similarity	NPD4194	Approved
0.7241	Intermediate Similarity	NPD4695	Discontinued
0.7222	Intermediate Similarity	NPD5329	Approved
0.7209	Intermediate Similarity	NPD3617	Approved
0.7204	Intermediate Similarity	NPD5207	Approved
0.7204	Intermediate Similarity	NPD5692	Phase 3
0.7174	Intermediate Similarity	NPD6672	Approved
0.7174	Intermediate Similarity	NPD5737	Approved
0.7143	Intermediate Similarity	NPD7521	Approved
0.7143	Intermediate Similarity	NPD7334	Approved
0.7143	Intermediate Similarity	NPD4690	Approved
0.7143	Intermediate Similarity	NPD6684	Approved
0.7143	Intermediate Similarity	NPD3618	Phase 1
0.7143	Intermediate Similarity	NPD7146	Approved
0.7143	Intermediate Similarity	NPD6409	Approved
0.7143	Intermediate Similarity	NPD4689	Approved
0.7143	Intermediate Similarity	NPD5279	Phase 3
0.7143	Intermediate Similarity	NPD4693	Phase 3
0.7143	Intermediate Similarity	NPD5205	Approved
0.7143	Intermediate Similarity	NPD4138	Approved
0.7143	Intermediate Similarity	NPD5330	Approved
0.7143	Intermediate Similarity	NPD4688	Approved
0.7128	Intermediate Similarity	NPD6079	Approved
0.7128	Intermediate Similarity	NPD5693	Phase 1
0.7128	Intermediate Similarity	NPD6050	Approved
0.7128	Intermediate Similarity	NPD7637	Suspended
0.7126	Intermediate Similarity	NPD4195	Approved
0.7113	Intermediate Similarity	NPD6083	Phase 2
0.7113	Intermediate Similarity	NPD6084	Phase 2
0.7097	Intermediate Similarity	NPD6904	Approved
0.7097	Intermediate Similarity	NPD4753	Phase 2
0.7097	Intermediate Similarity	NPD6080	Approved
0.7097	Intermediate Similarity	NPD6673	Approved
0.7083	Intermediate Similarity	NPD5210	Approved
0.7083	Intermediate Similarity	NPD5695	Phase 3
0.7083	Intermediate Similarity	NPD4629	Approved
0.7079	Intermediate Similarity	NPD3667	Approved
0.7053	Intermediate Similarity	NPD6399	Phase 3
0.7041	Intermediate Similarity	NPD5696	Approved
0.7033	Intermediate Similarity	NPD5363	Approved
0.7021	Intermediate Similarity	NPD5785	Approved
0.701	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.701	Intermediate Similarity	NPD5221	Approved
0.701	Intermediate Similarity	NPD5222	Approved
0.7	Intermediate Similarity	NPD5211	Phase 2
0.6989	Remote Similarity	NPD5208	Approved
0.6989	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6989	Remote Similarity	NPD6903	Approved
0.697	Remote Similarity	NPD7639	Approved
0.697	Remote Similarity	NPD7640	Approved
0.6947	Remote Similarity	NPD7515	Phase 2
0.6939	Remote Similarity	NPD5173	Approved
0.6923	Remote Similarity	NPD4786	Approved
0.6915	Remote Similarity	NPD5328	Approved
0.6893	Remote Similarity	NPD5697	Approved
0.6882	Remote Similarity	NPD3573	Approved
0.6869	Remote Similarity	NPD7638	Approved
0.6863	Remote Similarity	NPD5141	Approved
0.6842	Remote Similarity	NPD4096	Approved
0.6827	Remote Similarity	NPD6011	Approved
0.6827	Remote Similarity	NPD6899	Approved
0.6827	Remote Similarity	NPD6881	Approved
0.6809	Remote Similarity	NPD4518	Approved
0.6804	Remote Similarity	NPD7748	Approved
0.68	Remote Similarity	NPD5285	Approved
0.68	Remote Similarity	NPD4696	Approved
0.68	Remote Similarity	NPD5286	Approved
0.6789	Remote Similarity	NPD7115	Discovery
0.6774	Remote Similarity	NPD6098	Approved
0.6762	Remote Similarity	NPD6013	Approved
0.6762	Remote Similarity	NPD6014	Approved
0.6762	Remote Similarity	NPD6012	Approved
0.6739	Remote Similarity	NPD3668	Phase 3
0.6735	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6735	Remote Similarity	NPD5654	Approved
0.6733	Remote Similarity	NPD5223	Approved
0.6703	Remote Similarity	NPD4269	Approved
0.6703	Remote Similarity	NPD4270	Approved
0.6701	Remote Similarity	NPD4202	Approved
0.6701	Remote Similarity	NPD5133	Approved
0.6698	Remote Similarity	NPD6883	Approved
0.6698	Remote Similarity	NPD7290	Approved
0.6698	Remote Similarity	NPD7102	Approved
0.6667	Remote Similarity	NPD5225	Approved
0.6667	Remote Similarity	NPD5224	Approved
0.6667	Remote Similarity	NPD4252	Approved
0.6667	Remote Similarity	NPD4633	Approved
0.6667	Remote Similarity	NPD5226	Approved
0.6667	Remote Similarity	NPD7614	Phase 1
0.6667	Remote Similarity	NPD1694	Approved
0.6667	Remote Similarity	NPD4697	Phase 3
0.6667	Remote Similarity	NPD5091	Approved
0.6636	Remote Similarity	NPD6650	Approved
0.6636	Remote Similarity	NPD8130	Phase 1
0.6636	Remote Similarity	NPD6617	Approved
0.6636	Remote Similarity	NPD6869	Approved
0.6636	Remote Similarity	NPD6649	Approved
0.6636	Remote Similarity	NPD6847	Approved
0.6635	Remote Similarity	NPD6675	Approved
0.6635	Remote Similarity	NPD6402	Approved
0.6635	Remote Similarity	NPD7128	Approved
0.6635	Remote Similarity	NPD5739	Approved
0.6633	Remote Similarity	NPD6001	Approved
0.663	Remote Similarity	NPD4788	Approved
0.663	Remote Similarity	NPD5362	Discontinued
0.6602	Remote Similarity	NPD5174	Approved
0.6602	Remote Similarity	NPD5175	Approved
0.66	Remote Similarity	NPD5959	Approved
0.66	Remote Similarity	NPD7902	Approved
0.66	Remote Similarity	NPD4755	Approved
0.6574	Remote Similarity	NPD8297	Approved
0.6574	Remote Similarity	NPD6882	Approved
0.6571	Remote Similarity	NPD5701	Approved
0.6535	Remote Similarity	NPD4225	Approved
0.6522	Remote Similarity	NPD5209	Approved
0.6517	Remote Similarity	NPD4756	Discovery
0.6514	Remote Similarity	NPD4632	Approved
0.6509	Remote Similarity	NPD7320	Approved
0.6489	Remote Similarity	NPD1696	Phase 3
0.6489	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6484	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6484	Remote Similarity	NPD7514	Phase 3
0.6471	Remote Similarity	NPD4700	Approved
0.6465	Remote Similarity	NPD5769	Clinical (unspecified phase)
0.6456	Remote Similarity	NPD287	Approved
0.6449	Remote Similarity	NPD6373	Approved
0.6449	Remote Similarity	NPD6372	Approved
0.6444	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6444	Remote Similarity	NPD7145	Approved
0.6421	Remote Similarity	NPD5786	Approved
0.6415	Remote Similarity	NPD6614	Approved
0.6413	Remote Similarity	NPD8028	Phase 2
0.6413	Remote Similarity	NPD4692	Approved
0.6413	Remote Similarity	NPD4139	Approved
0.6413	Remote Similarity	NPD6902	Approved
0.6396	Remote Similarity	NPD6868	Approved
0.6395	Remote Similarity	NPD7143	Approved
0.6395	Remote Similarity	NPD7144	Approved
0.6364	Remote Similarity	NPD5778	Approved
0.6364	Remote Similarity	NPD5779	Approved
0.6355	Remote Similarity	NPD4730	Approved
0.6355	Remote Similarity	NPD5168	Approved
0.6355	Remote Similarity	NPD6686	Approved
0.6355	Remote Similarity	NPD4729	Approved
0.6346	Remote Similarity	NPD7632	Discontinued
0.6339	Remote Similarity	NPD6009	Approved
0.6339	Remote Similarity	NPD6317	Approved
0.6333	Remote Similarity	NPD6925	Approved
0.6333	Remote Similarity	NPD5776	Phase 2
0.633	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6322	Remote Similarity	NPD7151	Approved
0.6322	Remote Similarity	NPD7152	Approved
0.6322	Remote Similarity	NPD7150	Approved
0.6322	Remote Similarity	NPD6081	Approved
0.6311	Remote Similarity	NPD2066	Phase 3
0.631	Remote Similarity	NPD4224	Phase 2
0.6304	Remote Similarity	NPD7332	Phase 2
0.6304	Remote Similarity	NPD4819	Approved
0.6304	Remote Similarity	NPD4821	Approved
0.6304	Remote Similarity	NPD4822	Approved
0.6304	Remote Similarity	NPD5368	Approved
0.6304	Remote Similarity	NPD4820	Approved
0.63	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.63	Remote Similarity	NPD7900	Approved
0.63	Remote Similarity	NPD5122	Clinical (unspecified phase)
0.6292	Remote Similarity	NPD8039	Approved
0.6286	Remote Similarity	NPD4754	Approved
0.6286	Remote Similarity	NPD6052	Approved
0.6283	Remote Similarity	NPD6335	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