NPASS Compound

Structure

NPC25684 OpenBabel07101719242D 22 23 0 0 1 0 0 0 0 0999 V2000 3.4243 -0.3675 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9525 1.7154 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6885 2.4943 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6725 3.7329 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3402 2.3481 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9749 1.4173 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7604 -0.0527 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4227 2.0945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6913 0.3127 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.3290 2.4972 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2412 1.6000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6837 3.8819 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9860 1.2682 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8944 0.4473 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.4255 2.1692 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.7453 1.4361 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.7018 0.7124 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6944 3.4281 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3183 4.8128 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6906 0.5633 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.0602 3.1001 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 10 1 0 0 0 0 3 11 2 0 0 0 0 4 12 1 0 0 0 0 5 6 1 0 0 0 0 5 10 1 0 0 0 0 6 13 1 0 0 0 0 7 9 1 0 0 0 0 8 13 2 0 0 0 0 8 15 1 0 0 0 0 9 1 1 1 0 0 0 9 13 1 0 0 0 0 10 18 2 0 0 0 0 11 17 1 0 0 0 0 12 19 2 0 0 0 0 12 21 1 0 0 0 0 14 7 1 1 0 0 0 14 16 1 0 0 0 0 14 22 1 0 0 0 0 15 16 1 0 0 0 0 15 21 1 6 0 0 0 16 11 1 1 0 0 0 17 20 2 0 0 0 0 17 22 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	306.15
Volume:	316.244
LogP:	1.414
LogD:	1.617
LogS:	-1.95
# Rotatable Bonds:	5
TPSA:	69.67
# H-Bond Aceptor:	5
# H-Bond Donor:	0
# Rings:	2
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.453
Synthetic Accessibility Score:	4.301
Fsp3:	0.588
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	2
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.67
MDCK Permeability:	7.74481231928803e-05
Pgp-inhibitor:	0.009
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.06
20% Bioavailability (F20%):	0.022
30% Bioavailability (F30%):	0.343

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.109
Plasma Protein Binding (PPB):	76.57843017578125%
Volume Distribution (VD):	0.966
Pgp-substrate:	31.09029769897461%

ADMET: Metabolism

CYP1A2-inhibitor:	0.191
CYP1A2-substrate:	0.085
CYP2C19-inhibitor:	0.089
CYP2C19-substrate:	0.475
CYP2C9-inhibitor:	0.192
CYP2C9-substrate:	0.137
CYP2D6-inhibitor:	0.016
CYP2D6-substrate:	0.11
CYP3A4-inhibitor:	0.297
CYP3A4-substrate:	0.244

ADMET: Excretion

Clearance (CL):	3.432
Half-life (T1/2):	0.876

ADMET: Toxicity

hERG Blockers:	0.005
Human Hepatotoxicity (H-HT):	0.635
Drug-inuced Liver Injury (DILI):	0.843
AMES Toxicity:	0.093
Rat Oral Acute Toxicity:	0.33
Maximum Recommended Daily Dose:	0.527
Skin Sensitization:	0.211
Carcinogencity:	0.425
Eye Corrosion:	0.025
Eye Irritation:	0.095
Respiratory Toxicity:	0.964

Download Data

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

Natural Product: NPC25684

Natural Product ID:	NPC25684
*Common Name:**	Britanlin G
IUPAC Name:	[(3aR,4R,7S,8aR)-7-methyl-3-methylidene-2-oxo-6-(3-oxobutyl)-4,7,8,8a-tetrahydro-3aH-cyclohepta[b]furan-4-yl] acetate
Synonyms:
Standard InCHIKey:	MLXCWANLSPBFEG-LDYRWJSCSA-N
Standard InCHI:	InChI=1S/C17H22O5/c1-9-7-14-16(11(3)17(20)22-14)15(21-12(4)19)8-13(9)6-5-10(2)18/h8-9,14-16H,3,5-7H2,1-2,4H3/t9-,14+,15+,16+/m0/s1
SMILES:	CC(=O)CCC1=C[C@@H](OC(=O)C)[C@H]2[C@@H](C[C@@H]1C)OC(=O)C2=C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2426503
PubChem CID:	73355323
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones [CHEMONTID:0001543] Sesquiterpene lactones [CHEMONTID:0000502] Xanthanolides

*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
NPO32526	lineariifolia turcz	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[24044895]
NPO9124	Inula japonica	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27276091]
NPO9124	Inula japonica	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9124	Inula japonica	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9124	Inula japonica	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO9124	Inula japonica	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO9124	Inula japonica	Species	Asteraceae	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
NPT2257	Cell Line	MCF-10A	Homo sapiens	IC50	>	50000.0	nM	PMID[557471]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	IC50	=	28600.0	nM	PMID[557471]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	12600.0	nM	PMID[557471]
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	5500.0	nM	PMID[557472]

☑ 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 NPC25684 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	199
0.1-0.2	1247
0.2-0.3	5359
0.3-0.4	13624
0.4-0.5	11187
0.5-0.6	6652
0.6-0.7	3328
0.7-0.8	866
0.8-0.85	159
0.85-0.9	54
0.9-0.95	15
0.95-1	7

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC281949
1.0	High Similarity	NPC301477
0.9467	High Similarity	NPC65603
0.9467	High Similarity	NPC470240
0.9467	High Similarity	NPC476794
0.9375	High Similarity	NPC107787
0.9367	High Similarity	NPC115786
0.925	High Similarity	NPC165162
0.925	High Similarity	NPC78089
0.9231	High Similarity	NPC141810
0.92	High Similarity	NPC226669
0.92	High Similarity	NPC193351
0.92	High Similarity	NPC138408
0.9	High Similarity	NPC318468
0.8974	High Similarity	NPC270126
0.8974	High Similarity	NPC617
0.8961	High Similarity	NPC97516
0.8961	High Similarity	NPC171204
0.8961	High Similarity	NPC476028
0.8961	High Similarity	NPC141789
0.8875	High Similarity	NPC89555
0.8861	High Similarity	NPC302426
0.8831	High Similarity	NPC235906
0.8816	High Similarity	NPC140287
0.8816	High Similarity	NPC476355
0.88	High Similarity	NPC163003
0.878	High Similarity	NPC255307
0.8765	High Similarity	NPC474703
0.875	High Similarity	NPC255580
0.875	High Similarity	NPC471325
0.875	High Similarity	NPC39411
0.8734	High Similarity	NPC470239
0.8734	High Similarity	NPC63649
0.8734	High Similarity	NPC472965
0.8734	High Similarity	NPC178277
0.8734	High Similarity	NPC182550
0.8734	High Similarity	NPC470244
0.8734	High Similarity	NPC264227
0.8706	High Similarity	NPC129419
0.8701	High Similarity	NPC155587
0.8675	High Similarity	NPC50637
0.8675	High Similarity	NPC475461
0.8675	High Similarity	NPC305475
0.8659	High Similarity	NPC141193
0.8659	High Similarity	NPC159635
0.8659	High Similarity	NPC114979
0.8659	High Similarity	NPC191476
0.8659	High Similarity	NPC96259
0.8642	High Similarity	NPC173609
0.8625	High Similarity	NPC281132
0.8608	High Similarity	NPC128276
0.859	High Similarity	NPC123360
0.8588	High Similarity	NPC268298
0.8537	High Similarity	NPC131669
0.8537	High Similarity	NPC473390
0.8519	High Similarity	NPC35089
0.8519	High Similarity	NPC10276
0.8519	High Similarity	NPC470241
0.8481	Intermediate Similarity	NPC57744
0.8481	Intermediate Similarity	NPC187568
0.8481	Intermediate Similarity	NPC41780
0.8452	Intermediate Similarity	NPC150755
0.8442	Intermediate Similarity	NPC58956
0.8442	Intermediate Similarity	NPC269206
0.8442	Intermediate Similarity	NPC295633
0.8434	Intermediate Similarity	NPC476804
0.8421	Intermediate Similarity	NPC472955
0.8415	Intermediate Similarity	NPC229825
0.8395	Intermediate Similarity	NPC69271
0.8395	Intermediate Similarity	NPC74673
0.8395	Intermediate Similarity	NPC276356
0.8391	Intermediate Similarity	NPC150978
0.8391	Intermediate Similarity	NPC74103
0.8391	Intermediate Similarity	NPC123177
0.8391	Intermediate Similarity	NPC70595
0.8391	Intermediate Similarity	NPC284185
0.8375	Intermediate Similarity	NPC299235
0.8375	Intermediate Similarity	NPC93763
0.8375	Intermediate Similarity	NPC108816
0.8375	Intermediate Similarity	NPC472960
0.8372	Intermediate Similarity	NPC166919
0.8353	Intermediate Similarity	NPC231889
0.8333	Intermediate Similarity	NPC235792
0.8315	Intermediate Similarity	NPC67584
0.8313	Intermediate Similarity	NPC475947
0.8313	Intermediate Similarity	NPC272814
0.8313	Intermediate Similarity	NPC40746
0.8313	Intermediate Similarity	NPC215294
0.8313	Intermediate Similarity	NPC39588
0.8313	Intermediate Similarity	NPC169575
0.8295	Intermediate Similarity	NPC475302
0.8293	Intermediate Similarity	NPC42470
0.8293	Intermediate Similarity	NPC24417
0.8289	Intermediate Similarity	NPC144511
0.8289	Intermediate Similarity	NPC88877
0.8289	Intermediate Similarity	NPC296522
0.8289	Intermediate Similarity	NPC476591
0.8276	Intermediate Similarity	NPC475748
0.8276	Intermediate Similarity	NPC62815
0.8276	Intermediate Similarity	NPC253144
0.8276	Intermediate Similarity	NPC144133
0.8276	Intermediate Similarity	NPC179394
0.8276	Intermediate Similarity	NPC469368
0.8272	Intermediate Similarity	NPC98557
0.8272	Intermediate Similarity	NPC167881
0.8267	Intermediate Similarity	NPC194871
0.8256	Intermediate Similarity	NPC477302
0.825	Intermediate Similarity	NPC15975
0.825	Intermediate Similarity	NPC195785
0.825	Intermediate Similarity	NPC7563
0.825	Intermediate Similarity	NPC320630
0.825	Intermediate Similarity	NPC474760
0.825	Intermediate Similarity	NPC116177
0.8235	Intermediate Similarity	NPC38576
0.8235	Intermediate Similarity	NPC279859
0.8235	Intermediate Similarity	NPC64153
0.8235	Intermediate Similarity	NPC284902
0.8228	Intermediate Similarity	NPC244166
0.8222	Intermediate Similarity	NPC213078
0.8214	Intermediate Similarity	NPC158756
0.8214	Intermediate Similarity	NPC165287
0.8214	Intermediate Similarity	NPC156485
0.8205	Intermediate Similarity	NPC472956
0.8202	Intermediate Similarity	NPC477131
0.8202	Intermediate Similarity	NPC127019
0.8193	Intermediate Similarity	NPC35556
0.8182	Intermediate Similarity	NPC133698
0.8182	Intermediate Similarity	NPC20713
0.8171	Intermediate Similarity	NPC223904
0.8161	Intermediate Similarity	NPC206001
0.8161	Intermediate Similarity	NPC151770
0.8161	Intermediate Similarity	NPC218927
0.8158	Intermediate Similarity	NPC470256
0.8148	Intermediate Similarity	NPC267231
0.814	Intermediate Similarity	NPC237540
0.814	Intermediate Similarity	NPC475703
0.8132	Intermediate Similarity	NPC161493
0.8125	Intermediate Similarity	NPC472967
0.8125	Intermediate Similarity	NPC266159
0.8118	Intermediate Similarity	NPC21471
0.8118	Intermediate Similarity	NPC215364
0.8118	Intermediate Similarity	NPC470755
0.8118	Intermediate Similarity	NPC161957
0.8118	Intermediate Similarity	NPC33570
0.8111	Intermediate Similarity	NPC52044
0.8111	Intermediate Similarity	NPC304886
0.8111	Intermediate Similarity	NPC224689
0.8111	Intermediate Similarity	NPC213698
0.8101	Intermediate Similarity	NPC117746
0.8101	Intermediate Similarity	NPC259599
0.8101	Intermediate Similarity	NPC294434
0.8101	Intermediate Similarity	NPC15499
0.8095	Intermediate Similarity	NPC170286
0.8095	Intermediate Similarity	NPC475989
0.8095	Intermediate Similarity	NPC250315
0.8095	Intermediate Similarity	NPC54468
0.8095	Intermediate Similarity	NPC128429
0.8095	Intermediate Similarity	NPC59097
0.809	Intermediate Similarity	NPC476300
0.809	Intermediate Similarity	NPC228451
0.809	Intermediate Similarity	NPC475912
0.809	Intermediate Similarity	NPC125674
0.809	Intermediate Similarity	NPC469645
0.809	Intermediate Similarity	NPC475838
0.809	Intermediate Similarity	NPC469692
0.8077	Intermediate Similarity	NPC129665
0.8072	Intermediate Similarity	NPC52861
0.8068	Intermediate Similarity	NPC329857
0.8068	Intermediate Similarity	NPC469718
0.8068	Intermediate Similarity	NPC475855
0.8068	Intermediate Similarity	NPC51004
0.8049	Intermediate Similarity	NPC19841
0.8046	Intermediate Similarity	NPC471047
0.8046	Intermediate Similarity	NPC202672
0.8046	Intermediate Similarity	NPC224652
0.8046	Intermediate Similarity	NPC469628
0.8046	Intermediate Similarity	NPC475906
0.8046	Intermediate Similarity	NPC476805
0.8046	Intermediate Similarity	NPC469631
0.8046	Intermediate Similarity	NPC136879
0.8046	Intermediate Similarity	NPC469653
0.8046	Intermediate Similarity	NPC476803
0.8046	Intermediate Similarity	NPC475902
0.8043	Intermediate Similarity	NPC141191
0.8043	Intermediate Similarity	NPC54843
0.8023	Intermediate Similarity	NPC261721
0.8023	Intermediate Similarity	NPC238593
0.8023	Intermediate Similarity	NPC469483
0.8023	Intermediate Similarity	NPC469910
0.8022	Intermediate Similarity	NPC301596
0.8022	Intermediate Similarity	NPC299396
0.8022	Intermediate Similarity	NPC172998
0.8	Intermediate Similarity	NPC121825
0.8	Intermediate Similarity	NPC474338
0.8	Intermediate Similarity	NPC473330
0.8	Intermediate Similarity	NPC470013
0.8	Intermediate Similarity	NPC470010
0.8	Intermediate Similarity	NPC474247
0.8	Intermediate Similarity	NPC167219
0.8	Intermediate Similarity	NPC323008

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 NPC25684 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	183
0.1-0.2	1797
0.2-0.3	3871
0.3-0.4	2252
0.4-0.5	662
0.5-0.6	292
0.6-0.7	76
0.7-0.8	17
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
0.7955	Intermediate Similarity	NPD1695	Approved
0.7912	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7701	Intermediate Similarity	NPD1733	Clinical (unspecified phase)
0.7701	Intermediate Similarity	NPD1694	Approved
0.7558	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.73	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7283	Intermediate Similarity	NPD46	Approved
0.7283	Intermediate Similarity	NPD6698	Approved
0.7283	Intermediate Similarity	NPD5785	Approved
0.7273	Intermediate Similarity	NPD7154	Phase 3
0.7255	Intermediate Similarity	NPD6371	Approved
0.7159	Intermediate Similarity	NPD5209	Approved
0.7111	Intermediate Similarity	NPD5363	Approved
0.7089	Intermediate Similarity	NPD2685	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD6435	Approved
0.6966	Remote Similarity	NPD4270	Approved
0.6966	Remote Similarity	NPD4269	Approved
0.6941	Remote Similarity	NPD8039	Approved
0.6939	Remote Similarity	NPD4225	Approved
0.6932	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6915	Remote Similarity	NPD7838	Discovery
0.6889	Remote Similarity	NPD5362	Discontinued
0.6854	Remote Similarity	NPD5369	Approved
0.6848	Remote Similarity	NPD5786	Approved
0.6771	Remote Similarity	NPD6399	Phase 3
0.6742	Remote Similarity	NPD4819	Approved
0.6742	Remote Similarity	NPD4822	Approved
0.6742	Remote Similarity	NPD4820	Approved
0.6742	Remote Similarity	NPD4821	Approved
0.6742	Remote Similarity	NPD4252	Approved
0.6742	Remote Similarity	NPD5368	Approved
0.6705	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6705	Remote Similarity	NPD4268	Approved
0.6705	Remote Similarity	NPD4271	Approved
0.6701	Remote Similarity	NPD5282	Discontinued
0.6667	Remote Similarity	NPD6684	Approved
0.6667	Remote Similarity	NPD4249	Approved
0.6667	Remote Similarity	NPD7146	Approved
0.6667	Remote Similarity	NPD5330	Approved
0.6667	Remote Similarity	NPD7983	Approved
0.6667	Remote Similarity	NPD7521	Approved
0.6667	Remote Similarity	NPD7334	Approved
0.6667	Remote Similarity	NPD6409	Approved
0.6598	Remote Similarity	NPD5778	Approved
0.6598	Remote Similarity	NPD5779	Approved
0.6596	Remote Similarity	NPD4251	Approved
0.6596	Remote Similarity	NPD4250	Approved
0.6571	Remote Similarity	NPD6686	Approved
0.6542	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6531	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6531	Remote Similarity	NPD7900	Approved
0.6526	Remote Similarity	NPD6672	Approved
0.6526	Remote Similarity	NPD6903	Approved
0.6526	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6526	Remote Similarity	NPD5737	Approved
0.6495	Remote Similarity	NPD5693	Phase 1
0.6481	Remote Similarity	NPD6053	Discontinued
0.6458	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6458	Remote Similarity	NPD6101	Approved
0.6436	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6404	Remote Similarity	NPD4756	Discovery
0.6396	Remote Similarity	NPD7115	Discovery
0.6381	Remote Similarity	NPD6008	Approved
0.6344	Remote Similarity	NPD5332	Approved
0.6344	Remote Similarity	NPD5331	Approved
0.6337	Remote Similarity	NPD7902	Approved
0.6327	Remote Similarity	NPD6411	Approved
0.6304	Remote Similarity	NPD4790	Discontinued
0.63	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.63	Remote Similarity	NPD5695	Phase 3
0.6289	Remote Similarity	NPD5370	Suspended
0.6277	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6275	Remote Similarity	NPD7638	Approved
0.6275	Remote Similarity	NPD5696	Approved
0.6238	Remote Similarity	NPD7839	Suspended
0.6224	Remote Similarity	NPD5207	Approved
0.6214	Remote Similarity	NPD7639	Approved
0.6214	Remote Similarity	NPD7640	Approved
0.6214	Remote Similarity	NPD6648	Approved
0.62	Remote Similarity	NPD7748	Approved
0.6176	Remote Similarity	NPD6084	Phase 2
0.6176	Remote Similarity	NPD6083	Phase 2
0.6168	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6168	Remote Similarity	NPD5697	Approved
0.6162	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD5344	Discontinued
0.6147	Remote Similarity	NPD2067	Discontinued
0.6146	Remote Similarity	NPD6422	Discontinued
0.6122	Remote Similarity	NPD6051	Approved
0.6122	Remote Similarity	NPD6673	Approved
0.6122	Remote Similarity	NPD6904	Approved
0.6122	Remote Similarity	NPD6080	Approved
0.6111	Remote Similarity	NPD6881	Approved
0.6111	Remote Similarity	NPD6899	Approved
0.6105	Remote Similarity	NPD3668	Phase 3
0.6091	Remote Similarity	NPD6650	Approved
0.6091	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6091	Remote Similarity	NPD6649	Approved
0.6082	Remote Similarity	NPD3573	Approved
0.6075	Remote Similarity	NPD5739	Approved
0.6075	Remote Similarity	NPD7128	Approved
0.6075	Remote Similarity	NPD6675	Approved
0.6075	Remote Similarity	NPD6402	Approved
0.6064	Remote Similarity	NPD3667	Approved
0.6061	Remote Similarity	NPD5692	Phase 3
0.6055	Remote Similarity	NPD6372	Approved
0.6055	Remote Similarity	NPD6013	Approved
0.6055	Remote Similarity	NPD6014	Approved
0.6055	Remote Similarity	NPD6373	Approved
0.6055	Remote Similarity	NPD6012	Approved
0.6053	Remote Similarity	NPD6927	Phase 3
0.604	Remote Similarity	NPD6001	Approved
0.6022	Remote Similarity	NPD4695	Discontinued
0.602	Remote Similarity	NPD5208	Approved
0.6019	Remote Similarity	NPD5701	Approved
0.6	Remote Similarity	NPD7102	Approved
0.6	Remote Similarity	NPD7637	Suspended
0.6	Remote Similarity	NPD7331	Phase 2
0.6	Remote Similarity	NPD7290	Approved
0.6	Remote Similarity	NPD5694	Approved
0.6	Remote Similarity	NPD6050	Approved
0.6	Remote Similarity	NPD7515	Phase 2
0.6	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6	Remote Similarity	NPD6108	Clinical (unspecified phase)
0.6	Remote Similarity	NPD5284	Approved
0.6	Remote Similarity	NPD6883	Approved
0.6	Remote Similarity	NPD5281	Approved
0.5979	Remote Similarity	NPD3618	Phase 1
0.5979	Remote Similarity	NPD6098	Approved
0.5963	Remote Similarity	NPD7320	Approved
0.5963	Remote Similarity	NPD6011	Approved
0.5952	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.5946	Remote Similarity	NPD6847	Approved
0.5946	Remote Similarity	NPD8130	Phase 1
0.5946	Remote Similarity	NPD6869	Approved
0.5946	Remote Similarity	NPD6617	Approved
0.5938	Remote Similarity	NPD3666	Approved
0.5938	Remote Similarity	NPD4786	Approved
0.5938	Remote Similarity	NPD3133	Approved
0.5938	Remote Similarity	NPD3665	Phase 1
0.5922	Remote Similarity	NPD5349	Clinical (unspecified phase)
0.5909	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.5897	Remote Similarity	NPD8517	Approved
0.5897	Remote Similarity	NPD8513	Phase 3
0.5897	Remote Similarity	NPD8516	Approved
0.5897	Remote Similarity	NPD8515	Approved
0.5893	Remote Similarity	NPD8297	Approved
0.5893	Remote Similarity	NPD6882	Approved
0.5882	Remote Similarity	NPD7341	Phase 2
0.5844	Remote Similarity	NPD28	Approved
0.5844	Remote Similarity	NPD29	Approved
0.5842	Remote Similarity	NPD8035	Phase 2
0.5842	Remote Similarity	NPD8034	Phase 2
0.5833	Remote Similarity	NPD2664	Clinical (unspecified phase)
0.5825	Remote Similarity	NPD4629	Approved
0.5825	Remote Similarity	NPD5210	Approved
0.5816	Remote Similarity	NPD5279	Phase 3
0.58	Remote Similarity	NPD4753	Phase 2
0.5794	Remote Similarity	NPD5211	Phase 2
0.5766	Remote Similarity	NPD2182	Approved
0.5765	Remote Similarity	NPD3197	Phase 1
0.5755	Remote Similarity	NPD5286	Approved
0.5755	Remote Similarity	NPD4696	Approved
0.5755	Remote Similarity	NPD5285	Approved
0.5741	Remote Similarity	NPD6647	Phase 2
0.5741	Remote Similarity	NPD6052	Approved
0.5739	Remote Similarity	NPD6274	Approved
0.5729	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.5727	Remote Similarity	NPD6412	Phase 2
0.5726	Remote Similarity	NPD7260	Phase 2
0.5714	Remote Similarity	NPD4755	Approved
0.5698	Remote Similarity	NPD9496	Clinical (unspecified phase)
0.5696	Remote Similarity	NPD3172	Approved
0.5688	Remote Similarity	NPD5141	Approved
0.5686	Remote Similarity	NPD6079	Approved
0.5682	Remote Similarity	NPD229	Approved
0.5673	Remote Similarity	NPD5654	Approved
0.5667	Remote Similarity	NPD7642	Approved
0.5664	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.5664	Remote Similarity	NPD7116	Clinical (unspecified phase)
0.5657	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.5657	Remote Similarity	NPD4519	Discontinued
0.5657	Remote Similarity	NPD4623	Approved
0.5656	Remote Similarity	NPD8074	Phase 3
0.5648	Remote Similarity	NPD5225	Approved
0.5648	Remote Similarity	NPD7632	Discontinued
0.5648	Remote Similarity	NPD5224	Approved
0.5648	Remote Similarity	NPD5226	Approved
0.5648	Remote Similarity	NPD4633	Approved
0.5644	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.5644	Remote Similarity	NPD5328	Approved
0.5641	Remote Similarity	NPD7641	Discontinued
0.5632	Remote Similarity	NPD3704	Approved
0.5631	Remote Similarity	NPD5781	Clinical (unspecified phase)
0.5631	Remote Similarity	NPD4202	Approved
0.563	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.5625	Remote Similarity	NPD4266	Approved
0.5625	Remote Similarity	NPD3194	Approved
0.5625	Remote Similarity	NPD3195	Phase 2

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