NPASS Compound

Structure

CID137570 OpenBabel06191715492D 33 34 0 0 1 0 0 0 0 0999 V2000 -6.1297 -3.6416 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3977 -0.6416 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6656 -3.6416 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0676 1.8584 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2713 1.1076 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.8618 -2.6416 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9958 -2.1416 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.7278 -2.1416 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6656 -0.6416 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6656 0.3584 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0183 -1.2574 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.9188 -0.5538 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5629 -0.4188 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.2278 0.3972 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2637 -2.1416 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5317 -2.1416 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.5368 -0.5538 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1297 -2.6416 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5317 -1.1416 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5317 -4.1416 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9336 2.3584 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.7278 -1.1416 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3977 -2.6416 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7996 0.8584 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0523 -0.9986 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9336 0.3584 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.5317 -5.1416 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9336 3.3584 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7248 -1.6279 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.2278 0.3972 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3977 -3.6416 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7996 1.8584 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 18 1 0 0 0 0 2 19 1 0 0 0 0 3 20 1 0 0 0 0 4 21 1 0 0 0 0 6 7 1 0 0 0 0 6 8 1 0 0 0 0 7 18 2 0 0 0 0 8 22 1 0 0 0 0 9 10 1 0 0 0 0 9 19 1 0 0 0 0 11 13 1 0 0 0 0 11 25 1 0 0 0 0 12 14 2 0 0 0 0 12 22 1 0 0 0 0 13 26 1 0 0 0 0 14 30 1 0 0 0 0 15 18 1 0 0 0 0 16 19 2 0 0 0 0 16 23 1 0 0 0 0 17 22 2 0 0 0 0 17 30 1 0 0 0 0 20 27 2 0 0 0 0 20 31 1 0 0 0 0 21 28 2 0 0 0 0 21 32 1 0 0 0 0 23 15 1 1 0 0 0 23 31 1 0 0 0 0 24 10 1 1 0 0 0 24 26 1 0 0 0 0 24 32 1 0 0 0 0 25 29 2 0 0 0 0 25 33 1 0 0 0 0 26 5 1 6 0 0 0 26 33 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	460.25
Volume:	484.216
LogP:	4.23
LogD:	3.791
LogS:	-4.892
# Rotatable Bonds:	14
TPSA:	92.04
# H-Bond Aceptor:	7
# H-Bond Donor:	0
# Rings:	2
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.239
Synthetic Accessibility Score:	4.515
Fsp3:	0.577
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-4.732
MDCK Permeability:	5.181432788958773e-05
Pgp-inhibitor:	0.993
Pgp-substrate:	0.02
Human Intestinal Absorption (HIA):	0.152
20% Bioavailability (F20%):	0.858
30% Bioavailability (F30%):	0.982

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.501
Plasma Protein Binding (PPB):	88.32379913330078%
Volume Distribution (VD):	1.439
Pgp-substrate:	8.393963813781738%

ADMET: Metabolism

CYP1A2-inhibitor:	0.086
CYP1A2-substrate:	0.034
CYP2C19-inhibitor:	0.298
CYP2C19-substrate:	0.063
CYP2C9-inhibitor:	0.123
CYP2C9-substrate:	0.068
CYP2D6-inhibitor:	0.819
CYP2D6-substrate:	0.104
CYP3A4-inhibitor:	0.776
CYP3A4-substrate:	0.293

ADMET: Excretion

Clearance (CL):	5.719
Half-life (T1/2):	0.763

ADMET: Toxicity

hERG Blockers:	0.029
Human Hepatotoxicity (H-HT):	0.939
Drug-inuced Liver Injury (DILI):	0.779
AMES Toxicity:	0.019
Rat Oral Acute Toxicity:	0.304
Maximum Recommended Daily Dose:	0.919
Skin Sensitization:	0.269
Carcinogencity:	0.115
Eye Corrosion:	0.004
Eye Irritation:	0.029
Respiratory Toxicity:	0.844

Download Data

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

Natural Product: NPC137570

Natural Product ID:	NPC137570
*Common Name:**	Irciformonin F
IUPAC Name:	[(1R,4E,6S,8E)-6-acetyloxy-11-(furan-3-yl)-4,8-dimethyl-1-[(2S)-2-methyl-5-oxooxolan-2-yl]undeca-4,8-dienyl] acetate
Synonyms:	Irciformonin F
Standard InCHIKey:	FKFCRXIWISWTQT-NEQWESOKSA-N
Standard InCHI:	InChI=1S/C26H36O7/c1-18(7-6-8-22-12-14-30-17-22)15-23(31-20(3)27)16-19(2)9-10-24(32-21(4)28)26(5)13-11-25(29)33-26/h7,12,14,16-17,23-24H,6,8-11,13,15H2,1-5H3/b18-7+,19-16+/t23-,24+,26-/m0/s1
SMILES:	C/C(=CCCc1ccoc1)/C[C@@H](/C=C(C)/CC[C@H]([C@]1(C)CCC(=O)O1)OC(=O)C)OC(=O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1823122
PubChem CID:	54669793
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO30704	Ircinia	Genus	Irciniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[21902186]

☑ 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	3
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT111	Cell Line	K562	Homo sapiens	IC50	=	10200.0	nM	PMID[470991]
NPT579	Cell Line	DLD-1	Homo sapiens	IC50	=	600.0	nM	PMID[470991]
NPT65	Cell Line	HepG2	Homo sapiens	IC50	=	1700.0	nM	PMID[470991]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	7000.0	nM	PMID[470991]

☑ 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 NPC137570 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	279
0.1-0.2	1339
0.2-0.3	3925
0.3-0.4	9099
0.4-0.5	11047
0.5-0.6	9132
0.6-0.7	7012
0.7-0.8	748
0.8-0.85	95
0.85-0.9	17
0.9-0.95	1
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9597	High Similarity	NPC45358
0.9516	High Similarity	NPC17681
0.944	High Similarity	NPC97740
0.9194	High Similarity	NPC473355
0.9194	High Similarity	NPC471554
0.9194	High Similarity	NPC471573
0.9194	High Similarity	NPC471501
0.8889	High Similarity	NPC476016
0.888	High Similarity	NPC471559
0.881	High Similarity	NPC329922
0.881	High Similarity	NPC474260
0.881	High Similarity	NPC329694
0.881	High Similarity	NPC81912
0.873	High Similarity	NPC71274
0.873	High Similarity	NPC75557
0.8699	High Similarity	NPC473969
0.8676	High Similarity	NPC80635
0.8672	High Similarity	NPC474279
0.8672	High Similarity	NPC474438
0.8636	High Similarity	NPC14650
0.8594	High Similarity	NPC474830
0.8571	High Similarity	NPC475818
0.8571	High Similarity	NPC476351
0.8561	High Similarity	NPC288209
0.855	High Similarity	NPC471545
0.855	High Similarity	NPC473344
0.855	High Similarity	NPC471544
0.8537	High Similarity	NPC144745
0.8537	High Similarity	NPC208906
0.8537	High Similarity	NPC131801
0.8525	High Similarity	NPC28054
0.8504	High Similarity	NPC65735
0.8504	High Similarity	NPC188377
0.85	High Similarity	NPC105249
0.8492	Intermediate Similarity	NPC283284
0.8492	Intermediate Similarity	NPC289911
0.848	Intermediate Similarity	NPC474817
0.8438	Intermediate Similarity	NPC474829
0.8413	Intermediate Similarity	NPC474136
0.8413	Intermediate Similarity	NPC1848
0.8403	Intermediate Similarity	NPC471521
0.8403	Intermediate Similarity	NPC473356
0.8397	Intermediate Similarity	NPC21460
0.8357	Intermediate Similarity	NPC475864
0.8346	Intermediate Similarity	NPC474425
0.8346	Intermediate Similarity	NPC471549
0.8346	Intermediate Similarity	NPC474407
0.8346	Intermediate Similarity	NPC473379
0.8346	Intermediate Similarity	NPC474426
0.8345	Intermediate Similarity	NPC307346
0.8345	Intermediate Similarity	NPC261733
0.8345	Intermediate Similarity	NPC218712
0.8345	Intermediate Similarity	NPC251865
0.8345	Intermediate Similarity	NPC267004
0.8322	Intermediate Similarity	NPC18135
0.8321	Intermediate Similarity	NPC282973
0.831	Intermediate Similarity	NPC471001
0.8308	Intermediate Similarity	NPC95567
0.8308	Intermediate Similarity	NPC319140
0.8286	Intermediate Similarity	NPC34056
0.8286	Intermediate Similarity	NPC195920
0.8273	Intermediate Similarity	NPC223415
0.8273	Intermediate Similarity	NPC470741
0.8271	Intermediate Similarity	NPC471817
0.8254	Intermediate Similarity	NPC4898
0.8248	Intermediate Similarity	NPC90953
0.8239	Intermediate Similarity	NPC474255
0.8239	Intermediate Similarity	NPC471618
0.8239	Intermediate Similarity	NPC474220
0.8235	Intermediate Similarity	NPC186626
0.8214	Intermediate Similarity	NPC86935
0.8201	Intermediate Similarity	NPC121158
0.8195	Intermediate Similarity	NPC298190
0.8194	Intermediate Similarity	NPC116717
0.8194	Intermediate Similarity	NPC291150
0.8182	Intermediate Similarity	NPC474270
0.8182	Intermediate Similarity	NPC475904
0.8169	Intermediate Similarity	NPC221809
0.8169	Intermediate Similarity	NPC255414
0.8162	Intermediate Similarity	NPC303217
0.8154	Intermediate Similarity	NPC179354
0.8143	Intermediate Similarity	NPC110305
0.8143	Intermediate Similarity	NPC22248
0.8138	Intermediate Similarity	NPC268905
0.813	Intermediate Similarity	NPC26157
0.813	Intermediate Similarity	NPC1811
0.8129	Intermediate Similarity	NPC248795
0.8125	Intermediate Similarity	NPC5180
0.8102	Intermediate Similarity	NPC286130
0.8099	Intermediate Similarity	NPC470999
0.8088	Intermediate Similarity	NPC92941
0.8085	Intermediate Similarity	NPC137295
0.806	Intermediate Similarity	NPC89133
0.8056	Intermediate Similarity	NPC69647
0.8056	Intermediate Similarity	NPC125182
0.8042	Intermediate Similarity	NPC71821
0.8042	Intermediate Similarity	NPC474317
0.8042	Intermediate Similarity	NPC470941
0.8042	Intermediate Similarity	NPC250228
0.8041	Intermediate Similarity	NPC470118
0.8031	Intermediate Similarity	NPC243704
0.8029	Intermediate Similarity	NPC146872
0.8028	Intermediate Similarity	NPC37488
0.8027	Intermediate Similarity	NPC155939
0.8027	Intermediate Similarity	NPC214541
0.8027	Intermediate Similarity	NPC296807
0.8027	Intermediate Similarity	NPC141538
0.8027	Intermediate Similarity	NPC44675
0.8016	Intermediate Similarity	NPC45536
0.8014	Intermediate Similarity	NPC322546
0.8014	Intermediate Similarity	NPC474378
0.8014	Intermediate Similarity	NPC474219
0.8014	Intermediate Similarity	NPC308205
0.8014	Intermediate Similarity	NPC471002
0.8014	Intermediate Similarity	NPC29695
0.8014	Intermediate Similarity	NPC476201
0.8014	Intermediate Similarity	NPC182427
0.8	Intermediate Similarity	NPC156189
0.8	Intermediate Similarity	NPC16922
0.8	Intermediate Similarity	NPC20500
0.7986	Intermediate Similarity	NPC107571
0.7986	Intermediate Similarity	NPC474615
0.7986	Intermediate Similarity	NPC7388
0.7972	Intermediate Similarity	NPC104924
0.7971	Intermediate Similarity	NPC310830
0.7971	Intermediate Similarity	NPC215109
0.7971	Intermediate Similarity	NPC170604
0.7971	Intermediate Similarity	NPC470742
0.7971	Intermediate Similarity	NPC473268
0.7955	Intermediate Similarity	NPC74612
0.7953	Intermediate Similarity	NPC217180
0.7953	Intermediate Similarity	NPC312525
0.7945	Intermediate Similarity	NPC471000
0.7943	Intermediate Similarity	NPC473152
0.7939	Intermediate Similarity	NPC243269
0.7933	Intermediate Similarity	NPC191828
0.7931	Intermediate Similarity	NPC195325
0.7931	Intermediate Similarity	NPC470791
0.7931	Intermediate Similarity	NPC470790
0.7931	Intermediate Similarity	NPC472654
0.7931	Intermediate Similarity	NPC329180
0.7929	Intermediate Similarity	NPC56197
0.7929	Intermediate Similarity	NPC67003
0.7923	Intermediate Similarity	NPC317217
0.7919	Intermediate Similarity	NPC299038
0.7919	Intermediate Similarity	NPC36655
0.7919	Intermediate Similarity	NPC472778
0.7919	Intermediate Similarity	NPC261597
0.7919	Intermediate Similarity	NPC187149
0.7919	Intermediate Similarity	NPC197137
0.7919	Intermediate Similarity	NPC472777
0.7919	Intermediate Similarity	NPC472776
0.7917	Intermediate Similarity	NPC216755
0.7917	Intermediate Similarity	NPC471174
0.7914	Intermediate Similarity	NPC220094
0.7914	Intermediate Similarity	NPC476943
0.7914	Intermediate Similarity	NPC236532
0.7905	Intermediate Similarity	NPC476262
0.7891	Intermediate Similarity	NPC44577
0.7891	Intermediate Similarity	NPC75906
0.7887	Intermediate Similarity	NPC254198
0.7877	Intermediate Similarity	NPC477404
0.7877	Intermediate Similarity	NPC476122
0.7877	Intermediate Similarity	NPC196864
0.7867	Intermediate Similarity	NPC475226
0.7867	Intermediate Similarity	NPC475967
0.7867	Intermediate Similarity	NPC472779
0.7852	Intermediate Similarity	NPC469485
0.7852	Intermediate Similarity	NPC126723
0.7852	Intermediate Similarity	NPC209364
0.7852	Intermediate Similarity	NPC107646
0.7847	Intermediate Similarity	NPC346
0.7847	Intermediate Similarity	NPC276676
0.7846	Intermediate Similarity	NPC79557
0.7842	Intermediate Similarity	NPC310043
0.7838	Intermediate Similarity	NPC57998
0.7832	Intermediate Similarity	NPC199044
0.7832	Intermediate Similarity	NPC238843
0.7829	Intermediate Similarity	NPC469846
0.7826	Intermediate Similarity	NPC158525
0.782	Intermediate Similarity	NPC46536
0.782	Intermediate Similarity	NPC138139
0.7815	Intermediate Similarity	NPC305016
0.7812	Intermediate Similarity	NPC227660
0.781	Intermediate Similarity	NPC470740
0.7808	Intermediate Similarity	NPC234494
0.7803	Intermediate Similarity	NPC477965
0.7803	Intermediate Similarity	NPC118853
0.7803	Intermediate Similarity	NPC477038
0.7801	Intermediate Similarity	NPC90296
0.78	Intermediate Similarity	NPC470119
0.78	Intermediate Similarity	NPC45101
0.78	Intermediate Similarity	NPC173544
0.78	Intermediate Similarity	NPC475066
0.78	Intermediate Similarity	NPC214495
0.78	Intermediate Similarity	NPC167142
0.78	Intermediate Similarity	NPC469847
0.78	Intermediate Similarity	NPC286722
0.7795	Intermediate Similarity	NPC150895
0.7795	Intermediate Similarity	NPC205523

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 NPC137570 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	250
0.1-0.2	1048
0.2-0.3	2246
0.3-0.4	2726
0.4-0.5	1862
0.5-0.6	793
0.6-0.7	218
0.7-0.8	7
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
0.7448	Intermediate Similarity	NPD4628	Phase 3
0.7434	Intermediate Similarity	NPD5760	Phase 2
0.7434	Intermediate Similarity	NPD5761	Phase 2
0.7267	Intermediate Similarity	NPD920	Approved
0.7162	Intermediate Similarity	NPD3887	Approved
0.7143	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6832	Phase 2
0.7133	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7123	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7114	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7067	Intermediate Similarity	NPD6799	Approved
0.7025	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD919	Approved
0.7	Intermediate Similarity	NPD2181	Clinical (unspecified phase)
0.6987	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6985	Remote Similarity	NPD17	Approved
0.6964	Remote Similarity	NPD8434	Phase 2
0.6963	Remote Similarity	NPD9545	Approved
0.6939	Remote Similarity	NPD2796	Approved
0.6929	Remote Similarity	NPD1049	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6913	Remote Similarity	NPD1243	Approved
0.6903	Remote Similarity	NPD6599	Discontinued
0.6892	Remote Similarity	NPD2355	Clinical (unspecified phase)
0.6892	Remote Similarity	NPD2353	Approved
0.6871	Remote Similarity	NPD7033	Discontinued
0.6867	Remote Similarity	NPD6764	Approved
0.6867	Remote Similarity	NPD6765	Approved
0.6855	Remote Similarity	NPD7075	Discontinued
0.6842	Remote Similarity	NPD1241	Discontinued
0.6842	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD1608	Approved
0.6829	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6815	Remote Similarity	NPD6801	Discontinued
0.6781	Remote Similarity	NPD6355	Discontinued
0.6769	Remote Similarity	NPD1358	Approved
0.6765	Remote Similarity	NPD9092	Discovery
0.6763	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6761	Remote Similarity	NPD1019	Discontinued
0.6752	Remote Similarity	NPD6385	Approved
0.6752	Remote Similarity	NPD6386	Approved
0.6728	Remote Similarity	NPD1247	Approved
0.6714	Remote Similarity	NPD3972	Approved
0.6714	Remote Similarity	NPD9717	Approved
0.6712	Remote Similarity	NPD4307	Phase 2
0.6711	Remote Similarity	NPD1551	Phase 2
0.6711	Remote Similarity	NPD2354	Approved
0.671	Remote Similarity	NPD5403	Approved
0.6706	Remote Similarity	NPD6784	Approved
0.6706	Remote Similarity	NPD6785	Approved
0.669	Remote Similarity	NPD6798	Discontinued
0.669	Remote Similarity	NPD3764	Approved
0.6688	Remote Similarity	NPD5401	Approved
0.6687	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6652	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD1933	Approved
0.6667	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6002	Phase 3
0.6667	Remote Similarity	NPD2067	Discontinued
0.6667	Remote Similarity	NPD1471	Phase 3
0.6667	Remote Similarity	NPD5494	Approved
0.6667	Remote Similarity	NPD2344	Approved
0.6667	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7819	Suspended
0.6667	Remote Similarity	NPD6005	Phase 3
0.6667	Remote Similarity	NPD6004	Phase 3
0.6646	Remote Similarity	NPD7411	Suspended
0.6646	Remote Similarity	NPD3749	Approved
0.6645	Remote Similarity	NPD2186	Approved
0.6644	Remote Similarity	NPD2799	Discontinued
0.6644	Remote Similarity	NPD3748	Approved
0.6643	Remote Similarity	NPD5647	Approved
0.6623	Remote Similarity	NPD1549	Phase 2
0.6599	Remote Similarity	NPD3140	Approved
0.6599	Remote Similarity	NPD3142	Approved
0.6597	Remote Similarity	NPD9494	Approved
0.6591	Remote Similarity	NPD2182	Approved
0.6585	Remote Similarity	NPD6808	Phase 2
0.6584	Remote Similarity	NPD3882	Suspended
0.6575	Remote Similarity	NPD2313	Discontinued
0.6573	Remote Similarity	NPD3266	Approved
0.6573	Remote Similarity	NPD3267	Approved
0.6568	Remote Similarity	NPD6559	Discontinued
0.6565	Remote Similarity	NPD3134	Approved
0.6556	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6556	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6554	Remote Similarity	NPD447	Suspended
0.6554	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6545	Remote Similarity	NPD3926	Phase 2
0.6533	Remote Similarity	NPD4308	Phase 3
0.6531	Remote Similarity	NPD4062	Phase 3
0.6531	Remote Similarity	NPD6233	Phase 2
0.6522	Remote Similarity	NPD5353	Approved
0.6522	Remote Similarity	NPD5402	Approved
0.6522	Remote Similarity	NPD3817	Phase 2
0.65	Remote Similarity	NPD1778	Approved
0.6494	Remote Similarity	NPD2309	Approved
0.6474	Remote Similarity	NPD2533	Approved
0.6474	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6474	Remote Similarity	NPD3688	Clinical (unspecified phase)
0.6474	Remote Similarity	NPD2532	Approved
0.6474	Remote Similarity	NPD2534	Approved
0.6474	Remote Similarity	NPD3146	Approved
0.6467	Remote Similarity	NPD7097	Phase 1
0.6463	Remote Similarity	NPD3268	Approved
0.6458	Remote Similarity	NPD1203	Approved
0.6458	Remote Similarity	NPD2797	Approved
0.6443	Remote Similarity	NPD230	Phase 1
0.6442	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6433	Remote Similarity	NPD6273	Approved
0.6429	Remote Similarity	NPD3818	Discontinued
0.6429	Remote Similarity	NPD3750	Approved
0.6429	Remote Similarity	NPD2163	Approved
0.6429	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6423	Remote Similarity	NPD690	Clinical (unspecified phase)
0.6415	Remote Similarity	NPD3226	Approved
0.6415	Remote Similarity	NPD7458	Discontinued
0.6414	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6407	Remote Similarity	NPD4575	Clinical (unspecified phase)
0.64	Remote Similarity	NPD6653	Approved
0.6398	Remote Similarity	NPD6280	Approved
0.6398	Remote Similarity	NPD6279	Approved
0.6398	Remote Similarity	NPD1934	Approved
0.6397	Remote Similarity	NPD7843	Approved
0.6397	Remote Similarity	NPD5535	Approved
0.6395	Remote Similarity	NPD2598	Clinical (unspecified phase)
0.6391	Remote Similarity	NPD5844	Phase 1
0.6389	Remote Similarity	NPD1876	Approved
0.638	Remote Similarity	NPD7768	Phase 2
0.6376	Remote Similarity	NPD1240	Approved
0.6375	Remote Similarity	NPD4380	Phase 2
0.6369	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6369	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6358	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6357	Remote Similarity	NPD1894	Discontinued
0.6352	Remote Similarity	NPD957	Approved
0.6351	Remote Similarity	NPD1296	Phase 2
0.6347	Remote Similarity	NPD5242	Approved
0.6346	Remote Similarity	NPD7440	Discontinued
0.6345	Remote Similarity	NPD6362	Approved
0.6343	Remote Similarity	NPD2684	Approved
0.634	Remote Similarity	NPD2346	Discontinued
0.6338	Remote Similarity	NPD3496	Discontinued
0.6333	Remote Similarity	NPD4618	Approved
0.6333	Remote Similarity	NPD4622	Approved
0.6329	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.6329	Remote Similarity	NPD5049	Phase 3
0.6324	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.6323	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6323	Remote Similarity	NPD4110	Phase 3
0.6322	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6319	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD1510	Phase 2
0.6312	Remote Similarity	NPD5585	Approved
0.631	Remote Similarity	NPD7784	Clinical (unspecified phase)
0.6301	Remote Similarity	NPD2798	Approved
0.6299	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6299	Remote Similarity	NPD2897	Discontinued
0.6291	Remote Similarity	NPD1607	Approved
0.6288	Remote Similarity	NPD164	Approved
0.6284	Remote Similarity	NPD7095	Approved
0.6279	Remote Similarity	NPD7685	Pre-registration
0.6276	Remote Similarity	NPD3225	Approved
0.6275	Remote Similarity	NPD2935	Discontinued
0.6275	Remote Similarity	NPD2438	Suspended
0.6275	Remote Similarity	NPD2239	Approved
0.6275	Remote Similarity	NPD2240	Approved
0.6266	Remote Similarity	NPD4661	Approved
0.6266	Remote Similarity	NPD4662	Approved
0.6259	Remote Similarity	NPD7157	Approved
0.6258	Remote Similarity	NPD2654	Approved
0.6258	Remote Similarity	NPD2801	Approved
0.625	Remote Similarity	NPD5688	Approved
0.625	Remote Similarity	NPD5689	Approved
0.6242	Remote Similarity	NPD411	Approved
0.6241	Remote Similarity	NPD9697	Approved
0.6235	Remote Similarity	NPD958	Approved
0.6234	Remote Similarity	NPD5763	Approved
0.6234	Remote Similarity	NPD5762	Approved
0.6231	Remote Similarity	NPD1238	Approved
0.6228	Remote Similarity	NPD8127	Discontinued
0.6228	Remote Similarity	NPD7199	Phase 2
0.6225	Remote Similarity	NPD4340	Discontinued
0.6221	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.622	Remote Similarity	NPD5616	Clinical (unspecified phase)
0.6214	Remote Similarity	NPD9493	Approved
0.6213	Remote Similarity	NPD3451	Clinical (unspecified phase)
0.6213	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6211	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.62	Remote Similarity	NPD8032	Phase 2
0.6199	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6199	Remote Similarity	NPD7286	Phase 2
0.6197	Remote Similarity	NPD5691	Approved
0.6194	Remote Similarity	NPD4534	Discontinued
0.6194	Remote Similarity	NPD2424	Discontinued
0.6194	Remote Similarity	NPD5958	Discontinued
0.619	Remote Similarity	NPD5668	Clinical (unspecified phase)
0.6188	Remote Similarity	NPD3869	Phase 3

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