NPASS Compound

Structure

NPC210092 OpenBabel07101719142D 22 23 0 0 0 0 0 0 0 0999 V2000 -2.5981 6.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 6.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -0.0000 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 -0.8660 3.5000 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 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.0000 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 -2.5981 4.5000 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 3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 5.0000 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 13 1 0 0 0 0 2 13 1 0 0 0 0 3 4 2 0 0 0 0 3 7 1 0 0 0 0 4 9 1 0 0 0 0 5 6 3 0 0 0 0 5 8 1 0 0 0 0 6 10 1 0 0 0 0 7 14 2 0 0 0 0 8 15 1 0 0 0 0 9 16 2 0 0 0 0 10 21 1 0 0 0 0 11 13 1 0 0 0 0 11 17 1 0 0 0 0 12 14 1 0 0 0 0 12 15 2 0 0 0 0 14 16 1 0 0 0 0 15 22 1 0 0 0 0 16 18 1 0 0 0 0 17 19 2 0 0 0 0 17 21 1 0 0 0 0 18 20 2 0 0 0 0 18 22 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	298.12
Volume:	316.841
LogP:	3.577
LogD:	4.047
LogS:	-5.274
# Rotatable Bonds:	5
TPSA:	56.51
# H-Bond Aceptor:	4
# H-Bond Donor:	0
# Rings:	2
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.643
Synthetic Accessibility Score:	2.708
Fsp3:	0.333
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.538
MDCK Permeability:	2.9881792215746827e-05
Pgp-inhibitor:	0.999
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.905
30% Bioavailability (F30%):	0.968

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.148
Plasma Protein Binding (PPB):	95.72949981689453%
Volume Distribution (VD):	1.058
Pgp-substrate:	0.9337340593338013%

ADMET: Metabolism

CYP1A2-inhibitor:	0.974
CYP1A2-substrate:	0.183
CYP2C19-inhibitor:	0.96
CYP2C19-substrate:	0.256
CYP2C9-inhibitor:	0.949
CYP2C9-substrate:	0.87
CYP2D6-inhibitor:	0.037
CYP2D6-substrate:	0.499
CYP3A4-inhibitor:	0.293
CYP3A4-substrate:	0.31

ADMET: Excretion

Clearance (CL):	8.742
Half-life (T1/2):	0.558

ADMET: Toxicity

hERG Blockers:	0.017
Human Hepatotoxicity (H-HT):	0.866
Drug-inuced Liver Injury (DILI):	0.952
AMES Toxicity:	0.101
Rat Oral Acute Toxicity:	0.574
Maximum Recommended Daily Dose:	0.723
Skin Sensitization:	0.896
Carcinogencity:	0.858
Eye Corrosion:	0.035
Eye Irritation:	0.59
Respiratory Toxicity:	0.52

Download Data

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

Natural Product: NPC210092

Natural Product ID:	NPC210092
*Common Name:**	Capillarin Isovalerate
IUPAC Name:	4-(1-oxoisochromen-3-yl)but-2-ynyl 3-methylbutanoate
Synonyms:	Capillarin Isovalerate
Standard InCHIKey:	VOVINARUPGPNJR-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C18H18O4/c1-13(2)11-17(19)21-10-6-5-8-15-12-14-7-3-4-9-16(14)18(20)22-15/h3-4,7,9,12-13H,8,10-11H2,1-2H3
SMILES:	CC(C)CC(=O)OCC#CCc1cc2ccccc2c(=O)o1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL479331
PubChem CID:	11289514
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0001890] Isocoumarins and derivatives

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

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO21334	Artemisia dracunculus	Species	Asteraceae	Eukaryota	underground organs	n.a.	n.a.	PMID[14738379]
NPO21334	Artemisia dracunculus	Species	Asteraceae	Eukaryota	leaves	n.a.	n.a.	PMID[14738379]
NPO21334	Artemisia dracunculus	Species	Asteraceae	Eukaryota	dried aerial organs	n.a.	n.a.	PMID[14738379]
NPO21334	Artemisia dracunculus	Species	Asteraceae	Eukaryota	dried aerial organs	n.a.	n.a.	PMID[14738379]
NPO21334	Artemisia dracunculus	Species	Asteraceae	Eukaryota	roots and stolons	n.a.	n.a.	PMID[14738379]
NPO21334	Artemisia dracunculus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31815461]
NPO21334	Artemisia dracunculus	Species	Asteraceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO21334	Artemisia dracunculus	Species	Asteraceae	Eukaryota	Plant	n.a.	n.a.	Database[FooDB]
NPO21334	Artemisia dracunculus	Species	Asteraceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO21334	Artemisia dracunculus	Species	Asteraceae	Eukaryota	Shoot	n.a.	n.a.	Database[FooDB]
NPO21334	Artemisia dracunculus	Species	Asteraceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO21334	Artemisia dracunculus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO21334	Artemisia dracunculus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21334	Artemisia dracunculus	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
EC50	1
MIC	1
Others	1

Activity Type	# Activity
Organism	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1198	Organism	Magnaporthe grisea	Magnaporthe grisea	MIC	=	25.0	ug.mL-1	PMID[547034]
NPT1198	Organism	Magnaporthe grisea	Magnaporthe grisea	EC90	=	13.0	ug ml-1	PMID[547034]
NPT1198	Organism	Magnaporthe grisea	Magnaporthe grisea	EC50	=	5.0	ug.mL-1	PMID[547034]

☑ 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 NPC210092 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	333
0.1-0.2	1543
0.2-0.3	4151
0.3-0.4	10363
0.4-0.5	8788
0.5-0.6	6258
0.6-0.7	9121
0.7-0.8	2046
0.8-0.85	71
0.85-0.9	15
0.9-0.95	5
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9434	High Similarity	NPC269023
0.9434	High Similarity	NPC99846
0.9273	High Similarity	NPC474685
0.9259	High Similarity	NPC474157
0.9151	High Similarity	NPC209632
0.9057	High Similarity	NPC114594
0.8991	High Similarity	NPC196246
0.8991	High Similarity	NPC214067
0.8962	High Similarity	NPC60679
0.8919	High Similarity	NPC272524
0.8909	High Similarity	NPC305912
0.8909	High Similarity	NPC1082
0.8899	High Similarity	NPC17417
0.8899	High Similarity	NPC10251
0.8839	High Similarity	NPC308744
0.8829	High Similarity	NPC82899
0.8829	High Similarity	NPC270699
0.8818	High Similarity	NPC251854
0.8818	High Similarity	NPC93084
0.8807	High Similarity	NPC56493
0.8785	High Similarity	NPC301943
0.8785	High Similarity	NPC474365
0.8739	High Similarity	NPC243355
0.8716	High Similarity	NPC30594
0.8716	High Similarity	NPC37622
0.8716	High Similarity	NPC119271
0.8679	High Similarity	NPC146351
0.8673	High Similarity	NPC307651
0.8673	High Similarity	NPC153053
0.8649	High Similarity	NPC174099
0.8585	High Similarity	NPC225060
0.8585	High Similarity	NPC78701
0.8585	High Similarity	NPC35448
0.8584	High Similarity	NPC128368
0.8571	High Similarity	NPC210089
0.8571	High Similarity	NPC476003
0.8559	High Similarity	NPC83628
0.8559	High Similarity	NPC265407
0.8559	High Similarity	NPC469636
0.8559	High Similarity	NPC474364
0.8532	High Similarity	NPC31786
0.8522	High Similarity	NPC100353
0.8522	High Similarity	NPC149691
0.8505	High Similarity	NPC325497
0.8496	Intermediate Similarity	NPC321852
0.8491	Intermediate Similarity	NPC276775
0.8491	Intermediate Similarity	NPC92754
0.8491	Intermediate Similarity	NPC249912
0.8455	Intermediate Similarity	NPC269457
0.844	Intermediate Similarity	NPC89886
0.8426	Intermediate Similarity	NPC42211
0.8407	Intermediate Similarity	NPC260818
0.8348	Intermediate Similarity	NPC196075
0.8333	Intermediate Similarity	NPC118343
0.8319	Intermediate Similarity	NPC473243
0.8302	Intermediate Similarity	NPC130398
0.8276	Intermediate Similarity	NPC228936
0.8261	Intermediate Similarity	NPC161611
0.8257	Intermediate Similarity	NPC70624
0.825	Intermediate Similarity	NPC50872
0.8246	Intermediate Similarity	NPC167504
0.823	Intermediate Similarity	NPC85493
0.819	Intermediate Similarity	NPC477411
0.8182	Intermediate Similarity	NPC45613
0.8174	Intermediate Similarity	NPC79496
0.8174	Intermediate Similarity	NPC212415
0.8165	Intermediate Similarity	NPC203925
0.8142	Intermediate Similarity	NPC470391
0.813	Intermediate Similarity	NPC246166
0.813	Intermediate Similarity	NPC295664
0.812	Intermediate Similarity	NPC474408
0.812	Intermediate Similarity	NPC474095
0.8103	Intermediate Similarity	NPC13784
0.8083	Intermediate Similarity	NPC204784
0.8051	Intermediate Similarity	NPC226093
0.8051	Intermediate Similarity	NPC135730
0.8018	Intermediate Similarity	NPC188895
0.8017	Intermediate Similarity	NPC474314
0.8	Intermediate Similarity	NPC273837
0.8	Intermediate Similarity	NPC51292
0.7966	Intermediate Similarity	NPC306740
0.7951	Intermediate Similarity	NPC144547
0.792	Intermediate Similarity	NPC121272
0.792	Intermediate Similarity	NPC275576
0.792	Intermediate Similarity	NPC476599
0.7913	Intermediate Similarity	NPC40178
0.7909	Intermediate Similarity	NPC229242
0.7891	Intermediate Similarity	NPC475478
0.7881	Intermediate Similarity	NPC474363
0.7869	Intermediate Similarity	NPC289432
0.7869	Intermediate Similarity	NPC232958
0.7869	Intermediate Similarity	NPC238861
0.7869	Intermediate Similarity	NPC988
0.7869	Intermediate Similarity	NPC77000
0.7863	Intermediate Similarity	NPC158282
0.7857	Intermediate Similarity	NPC169913
0.7851	Intermediate Similarity	NPC293424
0.7833	Intermediate Similarity	NPC190298
0.783	Intermediate Similarity	NPC173443
0.783	Intermediate Similarity	NPC220893
0.7829	Intermediate Similarity	NPC475569
0.7826	Intermediate Similarity	NPC47536
0.7823	Intermediate Similarity	NPC46634
0.7823	Intermediate Similarity	NPC223351
0.7818	Intermediate Similarity	NPC270654
0.7797	Intermediate Similarity	NPC474176
0.7795	Intermediate Similarity	NPC181715
0.7778	Intermediate Similarity	NPC291799
0.7778	Intermediate Similarity	NPC77273
0.7778	Intermediate Similarity	NPC470765
0.7769	Intermediate Similarity	NPC45104
0.7769	Intermediate Similarity	NPC469574
0.776	Intermediate Similarity	NPC51079
0.7759	Intermediate Similarity	NPC281604
0.7731	Intermediate Similarity	NPC237366
0.7719	Intermediate Similarity	NPC269644
0.7717	Intermediate Similarity	NPC470753
0.7717	Intermediate Similarity	NPC473220
0.771	Intermediate Similarity	NPC136608
0.771	Intermediate Similarity	NPC38420
0.7706	Intermediate Similarity	NPC261181
0.7706	Intermediate Similarity	NPC23453
0.7699	Intermediate Similarity	NPC284477
0.7685	Intermediate Similarity	NPC119631
0.768	Intermediate Similarity	NPC472703
0.7674	Intermediate Similarity	NPC147561
0.7674	Intermediate Similarity	NPC473247
0.7674	Intermediate Similarity	NPC471832
0.7652	Intermediate Similarity	NPC311339
0.7642	Intermediate Similarity	NPC89377
0.7642	Intermediate Similarity	NPC96625
0.7636	Intermediate Similarity	NPC5472
0.7632	Intermediate Similarity	NPC255676
0.7632	Intermediate Similarity	NPC234305
0.7623	Intermediate Similarity	NPC217423
0.7623	Intermediate Similarity	NPC228318
0.7623	Intermediate Similarity	NPC45794
0.7619	Intermediate Similarity	NPC471466
0.7619	Intermediate Similarity	NPC472704
0.7619	Intermediate Similarity	NPC228739
0.7615	Intermediate Similarity	NPC470278
0.7611	Intermediate Similarity	NPC282895
0.7611	Intermediate Similarity	NPC112552
0.7603	Intermediate Similarity	NPC471616
0.7597	Intermediate Similarity	NPC2596
0.7593	Intermediate Similarity	NPC240108
0.7593	Intermediate Similarity	NPC213156
0.7586	Intermediate Similarity	NPC477251
0.7586	Intermediate Similarity	NPC475203
0.7586	Intermediate Similarity	NPC472315
0.7586	Intermediate Similarity	NPC474376
0.7586	Intermediate Similarity	NPC472316
0.7581	Intermediate Similarity	NPC72977
0.757	Intermediate Similarity	NPC304760
0.7565	Intermediate Similarity	NPC85977
0.7565	Intermediate Similarity	NPC329282
0.7563	Intermediate Similarity	NPC66208
0.7559	Intermediate Similarity	NPC91475
0.7559	Intermediate Similarity	NPC470163
0.7559	Intermediate Similarity	NPC470162
0.7559	Intermediate Similarity	NPC265910
0.7557	Intermediate Similarity	NPC472394
0.7557	Intermediate Similarity	NPC238370
0.7547	Intermediate Similarity	NPC318107
0.7544	Intermediate Similarity	NPC304873
0.7538	Intermediate Similarity	NPC238309
0.7522	Intermediate Similarity	NPC98911
0.7522	Intermediate Similarity	NPC472318
0.7521	Intermediate Similarity	NPC470764
0.7521	Intermediate Similarity	NPC20485
0.7521	Intermediate Similarity	NPC156648
0.7521	Intermediate Similarity	NPC221275
0.7521	Intermediate Similarity	NPC186933
0.7519	Intermediate Similarity	NPC51448
0.7519	Intermediate Similarity	NPC115797
0.7519	Intermediate Similarity	NPC37512
0.75	Intermediate Similarity	NPC137416
0.75	Intermediate Similarity	NPC9822
0.75	Intermediate Similarity	NPC49938
0.75	Intermediate Similarity	NPC90522
0.75	Intermediate Similarity	NPC472656
0.75	Intermediate Similarity	NPC328459
0.7481	Intermediate Similarity	NPC475195
0.7481	Intermediate Similarity	NPC72915
0.7481	Intermediate Similarity	NPC469519
0.748	Intermediate Similarity	NPC469954
0.748	Intermediate Similarity	NPC85511
0.7479	Intermediate Similarity	NPC137315
0.7459	Intermediate Similarity	NPC188907
0.7459	Intermediate Similarity	NPC220540
0.7456	Intermediate Similarity	NPC473325
0.7453	Intermediate Similarity	NPC58616
0.7453	Intermediate Similarity	NPC294134
0.7453	Intermediate Similarity	NPC53299
0.7444	Intermediate Similarity	NPC126516
0.7444	Intermediate Similarity	NPC48929
0.7444	Intermediate Similarity	NPC203486
0.7444	Intermediate Similarity	NPC43627
0.7444	Intermediate Similarity	NPC329913
0.7444	Intermediate Similarity	NPC472591

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 NPC210092 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	299
0.1-0.2	993
0.2-0.3	1319
0.3-0.4	2620
0.4-0.5	2141
0.5-0.6	1245
0.6-0.7	429
0.7-0.8	98
0.8-0.85	5
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8899	High Similarity	NPD2182	Approved
0.8739	High Similarity	NPD2181	Clinical (unspecified phase)
0.8532	High Similarity	NPD164	Approved
0.8333	Intermediate Similarity	NPD1238	Approved
0.8174	Intermediate Similarity	NPD1609	Clinical (unspecified phase)
0.7876	Intermediate Similarity	NPD5909	Discontinued
0.7869	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.7706	Intermediate Similarity	NPD1202	Approved
0.7692	Intermediate Similarity	NPD2067	Discontinued
0.7674	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7667	Intermediate Similarity	NPD690	Clinical (unspecified phase)
0.7607	Intermediate Similarity	NPD6831	Clinical (unspecified phase)
0.76	Intermediate Similarity	NPD6287	Discontinued
0.7597	Intermediate Similarity	NPD6832	Phase 2
0.7547	Intermediate Similarity	NPD9259	Approved
0.7547	Intermediate Similarity	NPD9257	Approved
0.7442	Intermediate Similarity	NPD6007	Clinical (unspecified phase)
0.744	Intermediate Similarity	NPD7163	Clinical (unspecified phase)
0.7438	Intermediate Similarity	NPD1241	Discontinued
0.7436	Intermediate Similarity	NPD3134	Approved
0.7422	Intermediate Similarity	NPD1876	Approved
0.7419	Intermediate Similarity	NPD9545	Approved
0.7411	Intermediate Similarity	NPD1989	Approved
0.7405	Intermediate Similarity	NPD7008	Discontinued
0.7377	Intermediate Similarity	NPD5951	Approved
0.7368	Intermediate Similarity	NPD2066	Phase 3
0.7328	Intermediate Similarity	NPD1931	Clinical (unspecified phase)
0.7328	Intermediate Similarity	NPD6647	Phase 2
0.7328	Intermediate Similarity	NPD1929	Approved
0.7328	Intermediate Similarity	NPD1930	Approved
0.7315	Intermediate Similarity	NPD1282	Approved
0.7308	Intermediate Similarity	NPD2798	Approved
0.7287	Intermediate Similarity	NPD2198	Approved
0.7287	Intermediate Similarity	NPD2199	Approved
0.7273	Intermediate Similarity	NPD3673	Approved
0.7273	Intermediate Similarity	NPD3672	Approved
0.7273	Intermediate Similarity	NPD9256	Approved
0.7273	Intermediate Similarity	NPD9258	Approved
0.7266	Intermediate Similarity	NPD6637	Approved
0.7266	Intermediate Similarity	NPD3972	Approved
0.7258	Intermediate Similarity	NPD9493	Approved
0.7239	Intermediate Similarity	NPD2979	Phase 3
0.7232	Intermediate Similarity	NPD5122	Clinical (unspecified phase)
0.7231	Intermediate Similarity	NPD3267	Approved
0.7231	Intermediate Similarity	NPD3266	Approved
0.7231	Intermediate Similarity	NPD2797	Approved
0.7227	Intermediate Similarity	NPD1358	Approved
0.7218	Intermediate Similarity	NPD3764	Approved
0.7188	Intermediate Similarity	NPD518	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD1281	Approved
0.7176	Intermediate Similarity	NPD1019	Discontinued
0.7165	Intermediate Similarity	NPD5306	Approved
0.7165	Intermediate Similarity	NPD5305	Approved
0.7156	Intermediate Similarity	NPD1087	Approved
0.7153	Intermediate Similarity	NPD2799	Discontinued
0.7153	Intermediate Similarity	NPD3748	Approved
0.7132	Intermediate Similarity	NPD9717	Approved
0.7119	Intermediate Similarity	NPD1237	Approved
0.7111	Intermediate Similarity	NPD4307	Phase 2
0.7097	Intermediate Similarity	NPD2629	Approved
0.709	Intermediate Similarity	NPD3268	Approved
0.709	Intermediate Similarity	NPD2313	Discontinued
0.7087	Intermediate Similarity	NPD5585	Approved
0.7087	Intermediate Similarity	NPD5691	Approved
0.708	Intermediate Similarity	NPD2569	Approved
0.708	Intermediate Similarity	NPD2567	Approved
0.7059	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7054	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.705	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.705	Intermediate Similarity	NPD2346	Discontinued
0.7049	Intermediate Similarity	NPD4141	Clinical (unspecified phase)
0.7031	Intermediate Similarity	NPD17	Approved
0.7023	Intermediate Similarity	NPD1283	Approved
0.7021	Intermediate Similarity	NPD4628	Phase 3
0.7021	Intermediate Similarity	NPD7003	Approved
0.7018	Intermediate Similarity	NPD9260	Approved
0.7014	Intermediate Similarity	NPD6273	Approved
0.7008	Intermediate Similarity	NPD1894	Discontinued
0.7	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.6991	Remote Similarity	NPD7631	Approved
0.6983	Remote Similarity	NPD5926	Approved
0.6983	Remote Similarity	NPD9495	Approved
0.6978	Remote Similarity	NPD2531	Phase 2
0.6978	Remote Similarity	NPD2438	Suspended
0.6977	Remote Similarity	NPD7457	Clinical (unspecified phase)
0.697	Remote Similarity	NPD1203	Approved
0.6967	Remote Similarity	NPD5239	Approved
0.6967	Remote Similarity	NPD5236	Approved
0.6967	Remote Similarity	NPD5237	Approved
0.6967	Remote Similarity	NPD5240	Approved
0.6967	Remote Similarity	NPD5235	Approved
0.6964	Remote Similarity	NPD1090	Approved
0.6964	Remote Similarity	NPD1089	Approved
0.6964	Remote Similarity	NPD1086	Approved
0.695	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6934	Remote Similarity	NPD1933	Approved
0.6929	Remote Similarity	NPD7702	Clinical (unspecified phase)
0.6929	Remote Similarity	NPD2347	Approved
0.6923	Remote Similarity	NPD7236	Approved
0.6917	Remote Similarity	NPD9697	Approved
0.6911	Remote Similarity	NPD2201	Approved
0.6906	Remote Similarity	NPD4308	Phase 3
0.6905	Remote Similarity	NPD4198	Discontinued
0.6903	Remote Similarity	NPD7609	Phase 3
0.6901	Remote Similarity	NPD3750	Approved
0.6894	Remote Similarity	NPD5667	Approved
0.6891	Remote Similarity	NPD9261	Approved
0.6889	Remote Similarity	NPD6039	Approved
0.6887	Remote Similarity	NPD9490	Approved
0.6875	Remote Similarity	NPD800	Approved
0.6871	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.687	Remote Similarity	NPD1608	Approved
0.687	Remote Similarity	NPD1693	Approved
0.6861	Remote Similarity	NPD3373	Approved
0.6861	Remote Similarity	NPD3142	Approved
0.6861	Remote Similarity	NPD3140	Approved
0.6857	Remote Similarity	NPD2935	Discontinued
0.6853	Remote Similarity	NPD3887	Approved
0.6847	Remote Similarity	NPD650	Approved
0.6842	Remote Similarity	NPD1088	Approved
0.6822	Remote Similarity	NPD1651	Approved
0.6822	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD4359	Approved
0.6812	Remote Similarity	NPD6355	Discontinued
0.6812	Remote Similarity	NPD4622	Approved
0.6812	Remote Similarity	NPD4618	Approved
0.6809	Remote Similarity	NPD6004	Phase 3
0.6809	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6809	Remote Similarity	NPD6002	Phase 3
0.6809	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6809	Remote Similarity	NPD6005	Phase 3
0.6807	Remote Similarity	NPD1932	Approved
0.68	Remote Similarity	NPD5535	Approved
0.68	Remote Similarity	NPD7094	Approved
0.68	Remote Similarity	NPD6858	Approved
0.68	Remote Similarity	NPD5277	Phase 2
0.6794	Remote Similarity	NPD4806	Approved
0.6794	Remote Similarity	NPD4807	Approved
0.6789	Remote Similarity	NPD9491	Approved
0.6788	Remote Similarity	NPD7961	Discontinued
0.6788	Remote Similarity	NPD7713	Phase 3
0.6788	Remote Similarity	NPD8032	Phase 2
0.6783	Remote Similarity	NPD1563	Approved
0.6783	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.678	Remote Similarity	NPD7798	Approved
0.6769	Remote Similarity	NPD4626	Approved
0.6763	Remote Similarity	NPD3528	Clinical (unspecified phase)
0.6759	Remote Similarity	NPD6799	Approved
0.6752	Remote Similarity	NPD3495	Discontinued
0.6748	Remote Similarity	NPD2329	Discontinued
0.6742	Remote Similarity	NPD4878	Approved
0.6738	Remote Similarity	NPD4477	Approved
0.6738	Remote Similarity	NPD2796	Approved
0.6738	Remote Similarity	NPD4476	Approved
0.6724	Remote Similarity	NPD688	Clinical (unspecified phase)
0.6718	Remote Similarity	NPD4136	Approved
0.6718	Remote Similarity	NPD3496	Discontinued
0.6718	Remote Similarity	NPD3847	Discontinued
0.6718	Remote Similarity	NPD4106	Approved
0.6718	Remote Similarity	NPD4135	Approved
0.6716	Remote Similarity	NPD552	Approved
0.6716	Remote Similarity	NPD9567	Approved
0.6716	Remote Similarity	NPD553	Approved
0.6715	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6715	Remote Similarity	NPD6798	Discontinued
0.6714	Remote Similarity	NPD5688	Approved
0.6714	Remote Similarity	NPD5689	Approved
0.6694	Remote Similarity	NPD3047	Approved
0.6694	Remote Similarity	NPD3046	Approved
0.6694	Remote Similarity	NPD3048	Approved
0.669	Remote Similarity	NPD7440	Discontinued
0.669	Remote Similarity	NPD6652	Clinical (unspecified phase)
0.669	Remote Similarity	NPD2355	Clinical (unspecified phase)
0.669	Remote Similarity	NPD2353	Approved
0.6689	Remote Similarity	NPD7819	Suspended
0.6689	Remote Similarity	NPD7239	Suspended
0.6667	Remote Similarity	NPD5740	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD9263	Approved
0.6667	Remote Similarity	NPD2788	Approved
0.6667	Remote Similarity	NPD4062	Phase 3
0.6667	Remote Similarity	NPD5647	Approved
0.6667	Remote Similarity	NPD6233	Phase 2
0.6667	Remote Similarity	NPD8166	Discontinued
0.6667	Remote Similarity	NPD6085	Phase 2
0.6667	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD9267	Approved
0.6667	Remote Similarity	NPD9264	Approved
0.6644	Remote Similarity	NPD7458	Discontinued
0.6644	Remote Similarity	NPD6591	Clinical (unspecified phase)
0.6643	Remote Similarity	NPD2897	Discontinued
0.6642	Remote Similarity	NPD6966	Discovery
0.6636	Remote Similarity	NPD3971	Phase 1
0.6636	Remote Similarity	NPD227	Approved
0.6636	Remote Similarity	NPD225	Approved
0.6622	Remote Similarity	NPD5403	Approved
0.662	Remote Similarity	NPD1551	Phase 2
0.6617	Remote Similarity	NPD1481	Phase 2
0.6614	Remote Similarity	NPD2652	Approved
0.6614	Remote Similarity	NPD2650	Approved
0.6613	Remote Similarity	NPD74	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