NPASS Compound

Structure

CID25666 OpenBabel06191715352D 26 28 0 0 1 0 0 0 0 0999 V2000 -3.8615 -5.0949 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0132 -1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3578 0.6045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8833 -4.8870 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1472 -1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5743 -3.9360 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5962 -3.7281 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2812 -1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2872 -2.7770 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5491 -1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 -1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5491 0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 -1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4152 -1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 -0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 -1.3090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.3090 -2.5691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.6180 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.8171 0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5878 -0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 -0.3090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.3601 -3.3122 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 1.1910 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5878 -0.8090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.4152 -0.3090 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 4 1 0 0 0 0 2 5 1 0 0 0 0 4 6 1 0 0 0 0 5 8 2 0 0 0 0 6 7 1 0 0 0 0 7 9 1 0 0 0 0 8 14 1 0 0 0 0 9 17 1 0 0 0 0 10 13 1 0 0 0 0 10 14 2 0 0 0 0 11 13 1 0 0 0 0 11 16 1 0 0 0 0 12 15 1 0 0 0 0 12 25 1 0 0 0 0 13 15 2 0 0 0 0 14 25 1 0 0 0 0 15 19 1 0 0 0 0 16 18 1 0 0 0 0 16 21 1 6 0 0 0 17 22 2 0 0 0 0 18 17 1 1 0 0 0 18 20 1 0 0 0 0 19 21 1 0 0 0 0 19 23 2 0 0 0 0 20 24 2 0 0 0 0 20 26 1 0 0 0 0 21 3 1 6 0 0 0 21 26 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	358.18
Volume:	374.235
LogP:	2.989
LogD:	1.945
LogS:	-4.26
# Rotatable Bonds:	6
TPSA:	69.67
# H-Bond Aceptor:	5
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.413
Synthetic Accessibility Score:	4.541
Fsp3:	0.571
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-4.792
MDCK Permeability:	2.487160418240819e-05
Pgp-inhibitor:	0.981
Pgp-substrate:	0.006
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.885
30% Bioavailability (F30%):	0.967

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.546
Plasma Protein Binding (PPB):	87.87914276123047%
Volume Distribution (VD):	1.454
Pgp-substrate:	18.950489044189453%

ADMET: Metabolism

CYP1A2-inhibitor:	0.823
CYP1A2-substrate:	0.651
CYP2C19-inhibitor:	0.905
CYP2C19-substrate:	0.785
CYP2C9-inhibitor:	0.619
CYP2C9-substrate:	0.09
CYP2D6-inhibitor:	0.122
CYP2D6-substrate:	0.097
CYP3A4-inhibitor:	0.907
CYP3A4-substrate:	0.567

ADMET: Excretion

Clearance (CL):	6.442
Half-life (T1/2):	0.439

ADMET: Toxicity

hERG Blockers:	0.008
Human Hepatotoxicity (H-HT):	0.828
Drug-inuced Liver Injury (DILI):	0.927
AMES Toxicity:	0.206
Rat Oral Acute Toxicity:	0.798
Maximum Recommended Daily Dose:	0.924
Skin Sensitization:	0.936
Carcinogencity:	0.552
Eye Corrosion:	0.004
Eye Irritation:	0.036
Respiratory Toxicity:	0.331

Download Data

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

Natural Product: NPC25666

Natural Product ID:	NPC25666
*Common Name:**	Monascin
IUPAC Name:	(3S,3aR,9aR)-3-hexanoyl-9a-methyl-6-[(E)-prop-1-enyl]-3,3a,4,8-tetrahydrofuro[3,2-g]isochromene-2,9-dione
Synonyms:	Monascin
Standard InCHIKey:	XXKNHBAFFJINCK-RVEJDSBJSA-N
Standard InCHI:	InChI=1S/C21H26O5/c1-4-6-7-9-17(22)18-16-11-13-10-14(8-5-2)25-12-15(13)19(23)21(16,3)26-20(18)24/h5,8,10,16,18H,4,6-7,9,11-12H2,1-3H3/b8-5+/t16-,18+,21-/m1/s1
SMILES:	CCCCCC(=O)[C@H]1C(=O)O[C@@]2([C@@H]1CC1=C(C2=O)COC(=C1)/C=C/C)C
Synthetic Gene Cluster:	BGC0000027;
ChEMBL Identifier:	CHEMBL1215463
PubChem CID:	12118082
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0001831] Carbonyl compounds [CHEMONTID:0000118] Ketones [CHEMONTID:0003487] Cyclic ketones [CHEMONTID:0004325] Cyclohexenones

*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
NPO32777	bulgaria inquinans icrm-184	Species	Bulgariaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20655237]
NPO20419	Buxus wallichiana	Species	Buxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18655	Clerodendranthus spicatus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11218	Monascus kaoliang gao liang hong qu	Species	Fellodistomidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18655	Clerodendranthus spicatus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20419	Buxus wallichiana	Species	Buxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20419	Buxus wallichiana	Species	Buxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO21030	Monascus kaoliang	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21629	Pometia eximia	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18655	Clerodendranthus spicatus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2704	Veratrum sabadilla	Species	Melanthiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20419	Buxus wallichiana	Species	Buxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17552	Senecio flammeus	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	6

Activity Type	# Activity
Cell Line	3
NON-MOLECULAR	1
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT397	Cell Line	NCI-H460	Homo sapiens	IC50	>	50000.0	nM	PMID[451314]
NPT762	Cell Line	A-431	Homo sapiens	IC50	=	17770.0	nM	PMID[451314]
NPT458	Cell Line	IGROV-1	Homo sapiens	IC50	>	30000.0	nM	PMID[451314]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	30640.0	nM	PMID[451314]
NPT2	Others	Unspecified		IC50	>	50000.0	nM	PMID[451314]
NPT2	Others	Unspecified		IC50	>	100000.0	nM	PMID[451314]

☑ 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 NPC25666 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	234
0.1-0.2	1233
0.2-0.3	4400
0.3-0.4	9822
0.4-0.5	15831
0.5-0.6	7615
0.6-0.7	3133
0.7-0.8	400
0.8-0.85	15
0.85-0.9	7
0.9-0.95	5
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC271059
0.9263	High Similarity	NPC31021
0.875	High Similarity	NPC166110
0.866	High Similarity	NPC248193
0.8557	High Similarity	NPC32944
0.8557	High Similarity	NPC193396
0.8542	High Similarity	NPC95364
0.8542	High Similarity	NPC142159
0.8532	High Similarity	NPC243298
0.84	Intermediate Similarity	NPC318082
0.8396	Intermediate Similarity	NPC23497
0.8378	Intermediate Similarity	NPC245320
0.8304	Intermediate Similarity	NPC476815
0.8304	Intermediate Similarity	NPC473145
0.8304	Intermediate Similarity	NPC31641
0.8125	Intermediate Similarity	NPC281172
0.8119	Intermediate Similarity	NPC471698
0.8091	Intermediate Similarity	NPC326264
0.8077	Intermediate Similarity	NPC471699
0.8077	Intermediate Similarity	NPC469851
0.8041	Intermediate Similarity	NPC291712
0.8037	Intermediate Similarity	NPC469853
0.8019	Intermediate Similarity	NPC272528
0.7928	Intermediate Similarity	NPC321496
0.7925	Intermediate Similarity	NPC473144
0.7925	Intermediate Similarity	NPC297281
0.79	Intermediate Similarity	NPC469372
0.7857	Intermediate Similarity	NPC203795
0.7857	Intermediate Similarity	NPC279859
0.7857	Intermediate Similarity	NPC38576
0.7843	Intermediate Similarity	NPC477130
0.7843	Intermediate Similarity	NPC477129
0.7843	Intermediate Similarity	NPC143210
0.78	Intermediate Similarity	NPC284561
0.7778	Intermediate Similarity	NPC32006
0.7778	Intermediate Similarity	NPC469852
0.7778	Intermediate Similarity	NPC85529
0.7768	Intermediate Similarity	NPC474271
0.7767	Intermediate Similarity	NPC295347
0.7767	Intermediate Similarity	NPC12727
0.7745	Intermediate Similarity	NPC1108
0.7736	Intermediate Similarity	NPC244456
0.7736	Intermediate Similarity	NPC469657
0.7723	Intermediate Similarity	NPC213636
0.7723	Intermediate Similarity	NPC212679
0.7723	Intermediate Similarity	NPC220454
0.7723	Intermediate Similarity	NPC469595
0.7723	Intermediate Similarity	NPC253177
0.7723	Intermediate Similarity	NPC280592
0.7714	Intermediate Similarity	NPC54843
0.7685	Intermediate Similarity	NPC474898
0.767	Intermediate Similarity	NPC38830
0.7647	Intermediate Similarity	NPC471329
0.7647	Intermediate Similarity	NPC32552
0.7647	Intermediate Similarity	NPC296114
0.7632	Intermediate Similarity	NPC270478
0.7624	Intermediate Similarity	NPC280833
0.7619	Intermediate Similarity	NPC208094
0.7619	Intermediate Similarity	NPC134083
0.7615	Intermediate Similarity	NPC477125
0.7586	Intermediate Similarity	NPC158963
0.757	Intermediate Similarity	NPC323441
0.7549	Intermediate Similarity	NPC224270
0.7547	Intermediate Similarity	NPC264378
0.7525	Intermediate Similarity	NPC477128
0.7524	Intermediate Similarity	NPC299396
0.7524	Intermediate Similarity	NPC301596
0.7524	Intermediate Similarity	NPC269492
0.7524	Intermediate Similarity	NPC172998
0.7524	Intermediate Similarity	NPC476275
0.7523	Intermediate Similarity	NPC476001
0.7523	Intermediate Similarity	NPC325769
0.7522	Intermediate Similarity	NPC66108
0.75	Intermediate Similarity	NPC469606
0.75	Intermediate Similarity	NPC470697
0.75	Intermediate Similarity	NPC31058
0.75	Intermediate Similarity	NPC273005
0.7478	Intermediate Similarity	NPC477509
0.7477	Intermediate Similarity	NPC215253
0.7477	Intermediate Similarity	NPC185253
0.7477	Intermediate Similarity	NPC46761
0.7476	Intermediate Similarity	NPC20713
0.7475	Intermediate Similarity	NPC159635
0.7455	Intermediate Similarity	NPC469607
0.7453	Intermediate Similarity	NPC84335
0.7453	Intermediate Similarity	NPC38530
0.7451	Intermediate Similarity	NPC173042
0.7451	Intermediate Similarity	NPC73995
0.7449	Intermediate Similarity	NPC221231
0.7449	Intermediate Similarity	NPC471326
0.7431	Intermediate Similarity	NPC471364
0.7431	Intermediate Similarity	NPC132395
0.7431	Intermediate Similarity	NPC471365
0.7431	Intermediate Similarity	NPC320294
0.7429	Intermediate Similarity	NPC470978
0.7429	Intermediate Similarity	NPC234339
0.7429	Intermediate Similarity	NPC470974
0.7429	Intermediate Similarity	NPC474947
0.7429	Intermediate Similarity	NPC273197
0.7426	Intermediate Similarity	NPC181327
0.7426	Intermediate Similarity	NPC471739
0.7411	Intermediate Similarity	NPC228477
0.7411	Intermediate Similarity	NPC137911
0.7411	Intermediate Similarity	NPC220705
0.7407	Intermediate Similarity	NPC194028
0.7407	Intermediate Similarity	NPC473384
0.7407	Intermediate Similarity	NPC472643
0.7407	Intermediate Similarity	NPC168319
0.7404	Intermediate Similarity	NPC476598
0.7404	Intermediate Similarity	NPC476597
0.7404	Intermediate Similarity	NPC165383
0.7404	Intermediate Similarity	NPC475302
0.7387	Intermediate Similarity	NPC199107
0.7387	Intermediate Similarity	NPC232969
0.7387	Intermediate Similarity	NPC133422
0.7383	Intermediate Similarity	NPC166770
0.7379	Intermediate Similarity	NPC152467
0.7379	Intermediate Similarity	NPC329857
0.7379	Intermediate Similarity	NPC469718
0.7379	Intermediate Similarity	NPC471818
0.7368	Intermediate Similarity	NPC265391
0.7364	Intermediate Similarity	NPC472756
0.7364	Intermediate Similarity	NPC470297
0.7358	Intermediate Similarity	NPC112654
0.7353	Intermediate Similarity	NPC472302
0.7353	Intermediate Similarity	NPC469628
0.7353	Intermediate Similarity	NPC475906
0.7353	Intermediate Similarity	NPC215831
0.7353	Intermediate Similarity	NPC475902
0.7353	Intermediate Similarity	NPC26078
0.7353	Intermediate Similarity	NPC469631
0.7353	Intermediate Similarity	NPC469653
0.7353	Intermediate Similarity	NPC471047
0.7353	Intermediate Similarity	NPC473658
0.735	Intermediate Similarity	NPC21326
0.735	Intermediate Similarity	NPC315974
0.7345	Intermediate Similarity	NPC478209
0.7339	Intermediate Similarity	NPC235369
0.7333	Intermediate Similarity	NPC476596
0.7333	Intermediate Similarity	NPC84893
0.7321	Intermediate Similarity	NPC327106
0.7321	Intermediate Similarity	NPC322903
0.7315	Intermediate Similarity	NPC469551
0.7315	Intermediate Similarity	NPC54705
0.7304	Intermediate Similarity	NPC159333
0.73	Intermediate Similarity	NPC30486
0.7297	Intermediate Similarity	NPC1679
0.7297	Intermediate Similarity	NPC478208
0.7297	Intermediate Similarity	NPC472645
0.7295	Intermediate Similarity	NPC476008
0.729	Intermediate Similarity	NPC478233
0.729	Intermediate Similarity	NPC2049
0.729	Intermediate Similarity	NPC110937
0.729	Intermediate Similarity	NPC239895
0.7288	Intermediate Similarity	NPC476107
0.7282	Intermediate Similarity	NPC118011
0.7282	Intermediate Similarity	NPC51358
0.7282	Intermediate Similarity	NPC36668
0.7282	Intermediate Similarity	NPC307092
0.7281	Intermediate Similarity	NPC474315
0.7281	Intermediate Similarity	NPC179798
0.7281	Intermediate Similarity	NPC304180
0.7273	Intermediate Similarity	NPC173609
0.7273	Intermediate Similarity	NPC473283
0.7273	Intermediate Similarity	NPC475526
0.7273	Intermediate Similarity	NPC320154
0.7273	Intermediate Similarity	NPC329345
0.7273	Intermediate Similarity	NPC24651
0.7264	Intermediate Similarity	NPC209355
0.7257	Intermediate Similarity	NPC469370
0.7257	Intermediate Similarity	NPC38154
0.7255	Intermediate Similarity	NPC125925
0.7255	Intermediate Similarity	NPC113370
0.7255	Intermediate Similarity	NPC476079
0.7255	Intermediate Similarity	NPC38885
0.7255	Intermediate Similarity	NPC103743
0.725	Intermediate Similarity	NPC312833
0.7248	Intermediate Similarity	NPC474912
0.7248	Intermediate Similarity	NPC474899
0.7238	Intermediate Similarity	NPC29798
0.7238	Intermediate Similarity	NPC282644
0.7232	Intermediate Similarity	NPC266514
0.7228	Intermediate Similarity	NPC307112
0.7228	Intermediate Similarity	NPC177932
0.7228	Intermediate Similarity	NPC290329
0.7228	Intermediate Similarity	NPC472686
0.7228	Intermediate Similarity	NPC189311
0.7222	Intermediate Similarity	NPC316598
0.7222	Intermediate Similarity	NPC35717
0.7217	Intermediate Similarity	NPC264634
0.7217	Intermediate Similarity	NPC147180
0.7213	Intermediate Similarity	NPC477745
0.7207	Intermediate Similarity	NPC471143
0.7207	Intermediate Similarity	NPC477510
0.7203	Intermediate Similarity	NPC284707
0.7203	Intermediate Similarity	NPC470420
0.72	Intermediate Similarity	NPC288281
0.72	Intermediate Similarity	NPC474703
0.72	Intermediate Similarity	NPC475989
0.72	Intermediate Similarity	NPC22611

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 NPC25666 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	199
0.1-0.2	1506
0.2-0.3	3599
0.3-0.4	2513
0.4-0.5	959
0.5-0.6	270
0.6-0.7	103
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
0.7228	Intermediate Similarity	NPD1694	Approved
0.6981	Remote Similarity	NPD5693	Phase 1
0.6981	Remote Similarity	NPD5694	Approved
0.6909	Remote Similarity	NPD5696	Approved
0.6887	Remote Similarity	NPD5692	Phase 3
0.6857	Remote Similarity	NPD5737	Approved
0.6857	Remote Similarity	NPD6672	Approved
0.6852	Remote Similarity	NPD5282	Discontinued
0.6833	Remote Similarity	NPD7115	Discovery
0.6822	Remote Similarity	NPD6050	Approved
0.6789	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6783	Remote Similarity	NPD5697	Approved
0.6765	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6759	Remote Similarity	NPD5779	Approved
0.6759	Remote Similarity	NPD5778	Approved
0.6729	Remote Similarity	NPD5207	Approved
0.6724	Remote Similarity	NPD6881	Approved
0.6724	Remote Similarity	NPD6011	Approved
0.6724	Remote Similarity	NPD6899	Approved
0.6696	Remote Similarity	NPD6675	Approved
0.6696	Remote Similarity	NPD6008	Approved
0.6696	Remote Similarity	NPD7128	Approved
0.6696	Remote Similarity	NPD6402	Approved
0.6696	Remote Similarity	NPD5739	Approved
0.6695	Remote Similarity	NPD6649	Approved
0.6695	Remote Similarity	NPD6650	Approved
0.6667	Remote Similarity	NPD6013	Approved
0.6667	Remote Similarity	NPD6372	Approved
0.6667	Remote Similarity	NPD6014	Approved
0.6667	Remote Similarity	NPD6373	Approved
0.6667	Remote Similarity	NPD6012	Approved
0.6639	Remote Similarity	NPD6053	Discontinued
0.6638	Remote Similarity	NPD5701	Approved
0.6636	Remote Similarity	NPD6673	Approved
0.6636	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6636	Remote Similarity	NPD6080	Approved
0.6636	Remote Similarity	NPD6904	Approved
0.6636	Remote Similarity	NPD6101	Approved
0.6636	Remote Similarity	NPD5695	Phase 3
0.6613	Remote Similarity	NPD8513	Phase 3
0.661	Remote Similarity	NPD6883	Approved
0.661	Remote Similarity	NPD7102	Approved
0.661	Remote Similarity	NPD7290	Approved
0.6607	Remote Similarity	NPD4225	Approved
0.6604	Remote Similarity	NPD3573	Approved
0.6602	Remote Similarity	NPD5209	Approved
0.66	Remote Similarity	NPD4756	Discovery
0.6581	Remote Similarity	NPD7320	Approved
0.6555	Remote Similarity	NPD8130	Phase 1
0.6555	Remote Similarity	NPD6847	Approved
0.6555	Remote Similarity	NPD6869	Approved
0.6555	Remote Similarity	NPD6617	Approved
0.6545	Remote Similarity	NPD7900	Approved
0.6545	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6538	Remote Similarity	NPD7260	Phase 2
0.6518	Remote Similarity	NPD6083	Phase 2
0.6518	Remote Similarity	NPD6084	Phase 2
0.6514	Remote Similarity	NPD5281	Approved
0.6514	Remote Similarity	NPD6411	Approved
0.6514	Remote Similarity	NPD5284	Approved
0.65	Remote Similarity	NPD8297	Approved
0.65	Remote Similarity	NPD6882	Approved
0.6496	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6486	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6486	Remote Similarity	NPD5654	Approved
0.648	Remote Similarity	NPD8516	Approved
0.648	Remote Similarity	NPD8515	Approved
0.648	Remote Similarity	NPD8517	Approved
0.6455	Remote Similarity	NPD6399	Phase 3
0.6422	Remote Similarity	NPD5785	Approved
0.6417	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.64	Remote Similarity	NPD8039	Approved
0.64	Remote Similarity	NPD6319	Approved
0.6372	Remote Similarity	NPD5959	Approved
0.6372	Remote Similarity	NPD7902	Approved
0.6356	Remote Similarity	NPD6614	Approved
0.6355	Remote Similarity	NPD7334	Approved
0.6355	Remote Similarity	NPD6409	Approved
0.6355	Remote Similarity	NPD5330	Approved
0.6355	Remote Similarity	NPD6684	Approved
0.6355	Remote Similarity	NPD6098	Approved
0.6355	Remote Similarity	NPD7521	Approved
0.6355	Remote Similarity	NPD7146	Approved
0.6339	Remote Similarity	NPD5210	Approved
0.6339	Remote Similarity	NPD4629	Approved
0.6333	Remote Similarity	NPD2067	Discontinued
0.633	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6328	Remote Similarity	NPD7492	Approved
0.6293	Remote Similarity	NPD5211	Phase 2
0.629	Remote Similarity	NPD6317	Approved
0.6279	Remote Similarity	NPD6616	Approved
0.627	Remote Similarity	NPD6054	Approved
0.6262	Remote Similarity	NPD5363	Approved
0.6262	Remote Similarity	NPD1696	Phase 3
0.6261	Remote Similarity	NPD5286	Approved
0.6261	Remote Similarity	NPD4696	Approved
0.6261	Remote Similarity	NPD5285	Approved
0.625	Remote Similarity	NPD7748	Approved
0.625	Remote Similarity	NPD6001	Approved
0.6241	Remote Similarity	NPD6845	Suspended
0.624	Remote Similarity	NPD6335	Approved
0.624	Remote Similarity	NPD6313	Approved
0.624	Remote Similarity	NPD6314	Approved
0.6239	Remote Similarity	NPD6903	Approved
0.6239	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6231	Remote Similarity	NPD8074	Phase 3
0.6231	Remote Similarity	NPD7078	Approved
0.6228	Remote Similarity	NPD4755	Approved
0.622	Remote Similarity	NPD6015	Approved
0.622	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.622	Remote Similarity	NPD6016	Approved
0.6218	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.621	Remote Similarity	NPD6274	Approved
0.6207	Remote Similarity	NPD5223	Approved
0.6204	Remote Similarity	NPD5786	Approved
0.619	Remote Similarity	NPD5369	Approved
0.619	Remote Similarity	NPD7100	Approved
0.619	Remote Similarity	NPD7101	Approved
0.6186	Remote Similarity	NPD5141	Approved
0.6183	Remote Similarity	NPD7736	Approved
0.6182	Remote Similarity	NPD1695	Approved
0.6179	Remote Similarity	NPD4632	Approved
0.6174	Remote Similarity	NPD7638	Approved
0.6172	Remote Similarity	NPD6370	Approved
0.6172	Remote Similarity	NPD5988	Approved
0.6167	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.616	Remote Similarity	NPD6009	Approved
0.6154	Remote Similarity	NPD5225	Approved
0.6154	Remote Similarity	NPD5226	Approved
0.6154	Remote Similarity	NPD4633	Approved
0.6154	Remote Similarity	NPD5224	Approved
0.6148	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6142	Remote Similarity	NPD6059	Approved
0.614	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.614	Remote Similarity	NPD4697	Phase 3
0.614	Remote Similarity	NPD5221	Approved
0.614	Remote Similarity	NPD5222	Approved
0.6132	Remote Similarity	NPD4270	Approved
0.6132	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.6132	Remote Similarity	NPD4269	Approved
0.6121	Remote Similarity	NPD7640	Approved
0.6121	Remote Similarity	NPD4700	Approved
0.6121	Remote Similarity	NPD7639	Approved
0.6111	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6107	Remote Similarity	NPD8293	Discontinued
0.6102	Remote Similarity	NPD5175	Approved
0.6102	Remote Similarity	NPD5174	Approved
0.6095	Remote Similarity	NPD4695	Discontinued
0.6094	Remote Similarity	NPD5983	Phase 2
0.6091	Remote Similarity	NPD5208	Approved
0.6087	Remote Similarity	NPD5173	Approved
0.6082	Remote Similarity	NPD6108	Clinical (unspecified phase)
0.608	Remote Similarity	NPD6868	Approved
0.6075	Remote Similarity	NPD7154	Phase 3
0.6071	Remote Similarity	NPD7983	Approved
0.6071	Remote Similarity	NPD7515	Phase 2
0.6066	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6066	Remote Similarity	NPD4634	Approved
0.6066	Remote Similarity	NPD6371	Approved
0.6058	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6055	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6055	Remote Similarity	NPD4694	Approved
0.6055	Remote Similarity	NPD3618	Phase 1
0.6055	Remote Similarity	NPD5279	Phase 3
0.6055	Remote Similarity	NPD5280	Approved
0.6036	Remote Similarity	NPD4753	Phase 2
0.6034	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6	Remote Similarity	NPD7604	Phase 2
0.6	Remote Similarity	NPD8328	Phase 3
0.5984	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.5983	Remote Similarity	NPD6648	Approved
0.5982	Remote Similarity	NPD46	Approved
0.5982	Remote Similarity	NPD6698	Approved
0.5969	Remote Similarity	NPD6909	Approved
0.5969	Remote Similarity	NPD6908	Approved
0.5966	Remote Similarity	NPD4754	Approved
0.5943	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.5943	Remote Similarity	NPD4252	Approved
0.5929	Remote Similarity	NPD6079	Approved
0.5909	Remote Similarity	NPD4519	Discontinued
0.5909	Remote Similarity	NPD6336	Discontinued
0.5909	Remote Similarity	NPD4623	Approved
0.5909	Remote Similarity	NPD5690	Phase 2
0.5902	Remote Similarity	NPD4729	Approved
0.5902	Remote Similarity	NPD4730	Approved
0.5893	Remote Similarity	NPD6051	Approved
0.5893	Remote Similarity	NPD5328	Approved
0.5877	Remote Similarity	NPD4202	Approved
0.5872	Remote Similarity	NPD4197	Approved
0.5872	Remote Similarity	NPD3668	Phase 3
0.5868	Remote Similarity	NPD4768	Approved
0.5868	Remote Similarity	NPD4767	Approved
0.5862	Remote Similarity	NPD7732	Phase 3
0.5862	Remote Similarity	NPD7839	Suspended
0.5846	Remote Similarity	NPD7503	Approved
0.5841	Remote Similarity	NPD7838	Discovery
0.5833	Remote Similarity	NPD6435	Approved
0.5833	Remote Similarity	NPD3667	Approved
0.5833	Remote Similarity	NPD6052	Approved
0.5822	Remote Similarity	NPD7236	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