NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	232.11
Volume:	246.776
LogP:	3.306
LogD:	3.314
LogS:	-3.287
# Rotatable Bonds:	4
TPSA:	35.53
# H-Bond Aceptor:	3
# H-Bond Donor:	0
# Rings:	2
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.748
Synthetic Accessibility Score:	2.81
Fsp3:	0.357
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:	-4.498
MDCK Permeability:	3.834618109976873e-05
Pgp-inhibitor:	0.053
Pgp-substrate:	0.006
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.059
30% Bioavailability (F30%):	0.976

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.398
Plasma Protein Binding (PPB):	92.99671173095703%
Volume Distribution (VD):	0.878
Pgp-substrate:	4.699079513549805%

ADMET: Metabolism

CYP1A2-inhibitor:	0.58
CYP1A2-substrate:	0.112
CYP2C19-inhibitor:	0.926
CYP2C19-substrate:	0.42
CYP2C9-inhibitor:	0.753
CYP2C9-substrate:	0.292
CYP2D6-inhibitor:	0.369
CYP2D6-substrate:	0.359
CYP3A4-inhibitor:	0.65
CYP3A4-substrate:	0.389

ADMET: Excretion

Clearance (CL):	10.448
Half-life (T1/2):	0.748

ADMET: Toxicity

hERG Blockers:	0.042
Human Hepatotoxicity (H-HT):	0.913
Drug-inuced Liver Injury (DILI):	0.035
AMES Toxicity:	0.162
Rat Oral Acute Toxicity:	0.014
Maximum Recommended Daily Dose:	0.959
Skin Sensitization:	0.963
Carcinogencity:	0.447
Eye Corrosion:	0.814
Eye Irritation:	0.98
Respiratory Toxicity:	0.926

Download Data

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

Natural Product: NPC23453

Natural Product ID:	NPC23453
*Common Name:**	Dihydrokawain
IUPAC Name:	(2S)-4-methoxy-2-(2-phenylethyl)-2,3-dihydropyran-6-one
Synonyms:	(+)-Dihydrokavain; Dihydrokawain
Standard InCHIKey:	VOOYTQRREPYRIW-LBPRGKRZSA-N
Standard InCHI:	InChI=1S/C14H16O3/c1-16-13-9-12(17-14(15)10-13)8-7-11-5-3-2-4-6-11/h2-6,10,12H,7-9H2,1H3/t12-/m0/s1
SMILES:	COC1=CC(=O)O[C@H](C1)CCc1ccccc1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL569329
PubChem CID:	10220256
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0001761] Kavalactones

*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
NPO26193	Piper methysticum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11830162]
NPO26193	Piper methysticum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12809361]
NPO26193	Piper methysticum	Species	Piperaceae	Eukaryota	root	n.a.	n.a.	PMID[25597012]
NPO26193	Piper methysticum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26193	Piper methysticum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26193	Piper methysticum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO26193	Piper methysticum	Species	Piperaceae	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	2
Others	17

Activity Type	# Activity
Organism	17
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified		IC50	=	60.0	ug.mL-1	PMID[449513]
NPT27	Others	Unspecified		IC50	=	175.0	ug.mL-1	PMID[449513]
NPT2567	Organism	Trichoderma viride	Hypocrea rufa	GI	=	16.2	%	PMID[449515]
NPT2567	Organism	Trichoderma viride	Hypocrea rufa	GI	=	0.0	%	PMID[449515]
NPT637	Organism	Fusarium oxysporum	Fusarium oxysporum	GI	=	21.7	%	PMID[449515]
NPT637	Organism	Fusarium oxysporum	Fusarium oxysporum	GI	=	10.1	%	PMID[449515]
NPT2600	Organism	Fusarium solani	Fusarium solani	GI	=	38.7	%	PMID[449515]
NPT2600	Organism	Fusarium solani	Fusarium solani	GI	=	0.0	%	PMID[449515]
NPT562	Organism	Colletotrichum gloeosporioides	Colletotrichum gloeosporioides	GI	=	33.3	%	PMID[449515]
NPT562	Organism	Colletotrichum gloeosporioides	Colletotrichum gloeosporioides	GI	=	0.0	%	PMID[449515]
NPT117	Organism	Echinochloa crus-galli	Echinochloa crus-galli	Inhibition	=	58.9	%	PMID[449515]
NPT117	Organism	Echinochloa crus-galli	Echinochloa crus-galli	Inhibition	=	53.1	%	PMID[449515]
NPT117	Organism	Echinochloa crus-galli	Echinochloa crus-galli	Inhibition	=	61.2	%	PMID[449515]
NPT117	Organism	Echinochloa crus-galli	Echinochloa crus-galli	Inhibition	=	56.6	%	PMID[449515]
NPT117	Organism	Echinochloa crus-galli	Echinochloa crus-galli	Inhibition	=	50.0	%	PMID[449515]
NPT117	Organism	Echinochloa crus-galli	Echinochloa crus-galli	Inhibition	=	46.7	%	PMID[449515]
NPT364	Organism	Lactuca sativa	Lactuca sativa	Inhibition	=	15.6	%	PMID[449515]
NPT364	Organism	Lactuca sativa	Lactuca sativa	Inhibition	=	74.3	%	PMID[449515]
NPT364	Organism	Lactuca sativa	Lactuca sativa	Inhibition	=	25.9	%	PMID[449515]

☑ 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 NPC23453 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	200
0.1-0.2	1089
0.2-0.3	3098
0.3-0.4	9456
0.4-0.5	13311
0.5-0.6	12593
0.6-0.7	2618
0.7-0.8	286
0.8-0.85	35
0.85-0.9	8
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.931	High Similarity	NPC169050
0.931	High Similarity	NPC96625
0.931	High Similarity	NPC286608
0.8736	High Similarity	NPC99240
0.8687	High Similarity	NPC477251
0.8652	High Similarity	NPC53299
0.8646	High Similarity	NPC98911
0.8646	High Similarity	NPC472318
0.8636	High Similarity	NPC324835
0.8636	High Similarity	NPC127491
0.8636	High Similarity	NPC308619
0.8587	High Similarity	NPC213156
0.8587	High Similarity	NPC240108
0.8571	High Similarity	NPC304760
0.8571	High Similarity	NPC234305
0.85	High Similarity	NPC136962
0.85	High Similarity	NPC475203
0.85	High Similarity	NPC472316
0.85	High Similarity	NPC472315
0.85	High Similarity	NPC474376
0.8485	Intermediate Similarity	NPC85977
0.8444	Intermediate Similarity	NPC475710
0.8409	Intermediate Similarity	NPC89950
0.8409	Intermediate Similarity	NPC71795
0.835	Intermediate Similarity	NPC474157
0.8333	Intermediate Similarity	NPC40178
0.83	Intermediate Similarity	NPC280616
0.83	Intermediate Similarity	NPC242913
0.83	Intermediate Similarity	NPC171831
0.828	Intermediate Similarity	NPC173443
0.8242	Intermediate Similarity	NPC58616
0.8235	Intermediate Similarity	NPC47536
0.8229	Intermediate Similarity	NPC5472
0.8211	Intermediate Similarity	NPC77273
0.8202	Intermediate Similarity	NPC303245
0.8182	Intermediate Similarity	NPC167577
0.8182	Intermediate Similarity	NPC78517
0.8182	Intermediate Similarity	NPC170484
0.8163	Intermediate Similarity	NPC154517
0.8137	Intermediate Similarity	NPC37115
0.8111	Intermediate Similarity	NPC103387
0.8111	Intermediate Similarity	NPC323103
0.8105	Intermediate Similarity	NPC119631
0.809	Intermediate Similarity	NPC121800
0.8085	Intermediate Similarity	NPC220893
0.8081	Intermediate Similarity	NPC80115
0.8077	Intermediate Similarity	NPC273837
0.8068	Intermediate Similarity	NPC176228
0.8065	Intermediate Similarity	NPC89377
0.8058	Intermediate Similarity	NPC277788
0.8046	Intermediate Similarity	NPC175393
0.8022	Intermediate Similarity	NPC208183
0.8022	Intermediate Similarity	NPC243289
0.8022	Intermediate Similarity	NPC270507
0.802	Intermediate Similarity	NPC82426
0.802	Intermediate Similarity	NPC91820
0.8	Intermediate Similarity	NPC185501
0.798	Intermediate Similarity	NPC135951
0.7963	Intermediate Similarity	NPC476476
0.7955	Intermediate Similarity	NPC3672
0.7955	Intermediate Similarity	NPC287790
0.7944	Intermediate Similarity	NPC308744
0.7925	Intermediate Similarity	NPC234376
0.7917	Intermediate Similarity	NPC472319
0.7885	Intermediate Similarity	NPC20485
0.7885	Intermediate Similarity	NPC472314
0.7885	Intermediate Similarity	NPC475465
0.7879	Intermediate Similarity	NPC325499
0.7879	Intermediate Similarity	NPC270654
0.7864	Intermediate Similarity	NPC209632
0.785	Intermediate Similarity	NPC265002
0.785	Intermediate Similarity	NPC272524
0.783	Intermediate Similarity	NPC323007
0.781	Intermediate Similarity	NPC182549
0.781	Intermediate Similarity	NPC114741
0.781	Intermediate Similarity	NPC469636
0.78	Intermediate Similarity	NPC78701
0.78	Intermediate Similarity	NPC35448
0.7768	Intermediate Similarity	NPC475827
0.7768	Intermediate Similarity	NPC474223
0.7767	Intermediate Similarity	NPC114594
0.7767	Intermediate Similarity	NPC109637
0.7757	Intermediate Similarity	NPC477250
0.7736	Intermediate Similarity	NPC149545
0.7723	Intermediate Similarity	NPC146351
0.7706	Intermediate Similarity	NPC210092
0.7706	Intermediate Similarity	NPC474685
0.77	Intermediate Similarity	NPC276775
0.77	Intermediate Similarity	NPC92754
0.77	Intermediate Similarity	NPC249912
0.7692	Intermediate Similarity	NPC473855
0.7692	Intermediate Similarity	NPC127676
0.7685	Intermediate Similarity	NPC128368
0.767	Intermediate Similarity	NPC474365
0.767	Intermediate Similarity	NPC179686
0.767	Intermediate Similarity	NPC60679
0.767	Intermediate Similarity	NPC301943
0.7664	Intermediate Similarity	NPC477247
0.766	Intermediate Similarity	NPC294134
0.7647	Intermediate Similarity	NPC42211
0.7642	Intermediate Similarity	NPC83628
0.7642	Intermediate Similarity	NPC269023
0.7642	Intermediate Similarity	NPC281604
0.7642	Intermediate Similarity	NPC265407
0.7642	Intermediate Similarity	NPC474364
0.7642	Intermediate Similarity	NPC99846
0.7636	Intermediate Similarity	NPC473507
0.7636	Intermediate Similarity	NPC471616
0.7624	Intermediate Similarity	NPC225060
0.7619	Intermediate Similarity	NPC176971
0.7619	Intermediate Similarity	NPC326447
0.7615	Intermediate Similarity	NPC87069
0.7596	Intermediate Similarity	NPC269644
0.7593	Intermediate Similarity	NPC139946
0.7568	Intermediate Similarity	NPC190298
0.7565	Intermediate Similarity	NPC474254
0.7565	Intermediate Similarity	NPC474159
0.7549	Intermediate Similarity	NPC325497
0.7549	Intermediate Similarity	NPC118343
0.7547	Intermediate Similarity	NPC151530
0.7547	Intermediate Similarity	NPC157473
0.7526	Intermediate Similarity	NPC9822
0.7524	Intermediate Similarity	NPC128730
0.7524	Intermediate Similarity	NPC472919
0.7523	Intermediate Similarity	NPC161611
0.75	Intermediate Similarity	NPC473809
0.75	Intermediate Similarity	NPC210089
0.75	Intermediate Similarity	NPC304638
0.75	Intermediate Similarity	NPC183700
0.75	Intermediate Similarity	NPC130398
0.75	Intermediate Similarity	NPC63345
0.7478	Intermediate Similarity	NPC475328
0.7477	Intermediate Similarity	NPC149691
0.7476	Intermediate Similarity	NPC70624
0.7474	Intermediate Similarity	NPC99482
0.7455	Intermediate Similarity	NPC307651
0.7453	Intermediate Similarity	NPC51174
0.7453	Intermediate Similarity	NPC30594
0.7453	Intermediate Similarity	NPC37622
0.7449	Intermediate Similarity	NPC108026
0.7447	Intermediate Similarity	NPC288903
0.7434	Intermediate Similarity	NPC64340
0.7431	Intermediate Similarity	NPC185840
0.7431	Intermediate Similarity	NPC474689
0.7426	Intermediate Similarity	NPC30361
0.7419	Intermediate Similarity	NPC165212
0.7411	Intermediate Similarity	NPC470820
0.7407	Intermediate Similarity	NPC75272
0.7407	Intermediate Similarity	NPC471954
0.7387	Intermediate Similarity	NPC41851
0.7383	Intermediate Similarity	NPC260952
0.7383	Intermediate Similarity	NPC470391
0.7383	Intermediate Similarity	NPC56493
0.7383	Intermediate Similarity	NPC156648
0.7379	Intermediate Similarity	NPC171843
0.7374	Intermediate Similarity	NPC476484
0.7373	Intermediate Similarity	NPC85830
0.7368	Intermediate Similarity	NPC304538
0.7364	Intermediate Similarity	NPC477245
0.7364	Intermediate Similarity	NPC199462
0.7364	Intermediate Similarity	NPC477246
0.7358	Intermediate Similarity	NPC139891
0.7358	Intermediate Similarity	NPC227255
0.7358	Intermediate Similarity	NPC238115
0.7358	Intermediate Similarity	NPC269457
0.7347	Intermediate Similarity	NPC231591
0.7345	Intermediate Similarity	NPC122117
0.7345	Intermediate Similarity	NPC84129
0.7345	Intermediate Similarity	NPC183154
0.7345	Intermediate Similarity	NPC263754
0.734	Intermediate Similarity	NPC121478
0.734	Intermediate Similarity	NPC106313
0.734	Intermediate Similarity	NPC73637
0.7339	Intermediate Similarity	NPC476003
0.7339	Intermediate Similarity	NPC25067
0.7339	Intermediate Similarity	NPC88868
0.7339	Intermediate Similarity	NPC231251
0.7315	Intermediate Similarity	NPC17417
0.7315	Intermediate Similarity	NPC10251
0.7315	Intermediate Similarity	NPC184633
0.7315	Intermediate Similarity	NPC206341
0.7308	Intermediate Similarity	NPC253746
0.7308	Intermediate Similarity	NPC469481
0.7304	Intermediate Similarity	NPC474222
0.7304	Intermediate Similarity	NPC475804
0.7304	Intermediate Similarity	NPC31314
0.7304	Intermediate Similarity	NPC193193
0.7297	Intermediate Similarity	NPC196075
0.7297	Intermediate Similarity	NPC477411
0.729	Intermediate Similarity	NPC92623
0.729	Intermediate Similarity	NPC119271
0.729	Intermediate Similarity	NPC135464
0.7282	Intermediate Similarity	NPC145052
0.7282	Intermediate Similarity	NPC179411
0.7281	Intermediate Similarity	NPC96705
0.7281	Intermediate Similarity	NPC89324
0.7273	Intermediate Similarity	NPC84288
0.7273	Intermediate Similarity	NPC474314
0.7273	Intermediate Similarity	NPC82899
0.7273	Intermediate Similarity	NPC470825

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 NPC23453 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	174
0.1-0.2	843
0.2-0.3	1207
0.3-0.4	3038
0.4-0.5	2337
0.5-0.6	1239
0.6-0.7	282
0.7-0.8	28
0.8-0.85	1
0.85-0.9	0
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.931	High Similarity	NPD1282	Approved
0.8119	Intermediate Similarity	NPD5909	Discontinued
0.8077	Intermediate Similarity	NPD2067	Discontinued
0.798	Intermediate Similarity	NPD5926	Approved
0.7664	Intermediate Similarity	NPD2181	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD3134	Approved
0.7549	Intermediate Similarity	NPD1238	Approved
0.7547	Intermediate Similarity	NPD1358	Approved
0.75	Intermediate Similarity	NPD6647	Phase 2
0.7449	Intermediate Similarity	NPD3672	Approved
0.7449	Intermediate Similarity	NPD3673	Approved
0.7426	Intermediate Similarity	NPD1989	Approved
0.7411	Intermediate Similarity	NPD694	Clinical (unspecified phase)
0.7358	Intermediate Similarity	NPD9697	Approved
0.7347	Intermediate Similarity	NPD689	Discontinued
0.7315	Intermediate Similarity	NPD2182	Approved
0.7273	Intermediate Similarity	NPD969	Suspended
0.7263	Intermediate Similarity	NPD3971	Phase 1
0.7228	Intermediate Similarity	NPD5122	Clinical (unspecified phase)
0.7217	Intermediate Similarity	NPD5691	Approved
0.7212	Intermediate Similarity	NPD7798	Approved
0.7207	Intermediate Similarity	NPD5535	Approved
0.7196	Intermediate Similarity	NPD5048	Discontinued
0.7143	Intermediate Similarity	NPD9716	Approved
0.7143	Intermediate Similarity	NPD2550	Approved
0.7143	Intermediate Similarity	NPD2558	Approved
0.7143	Intermediate Similarity	NPD2555	Approved
0.7143	Intermediate Similarity	NPD2552	Approved
0.7143	Intermediate Similarity	NPD1087	Approved
0.7143	Intermediate Similarity	NPD2553	Approved
0.7143	Intermediate Similarity	NPD6010	Discontinued
0.7143	Intermediate Similarity	NPD2549	Approved
0.713	Intermediate Similarity	NPD5706	Approved
0.713	Intermediate Similarity	NPD5705	Approved
0.713	Intermediate Similarity	NPD5704	Approved
0.7117	Intermediate Similarity	NPD1609	Clinical (unspecified phase)
0.7113	Intermediate Similarity	NPD5734	Clinical (unspecified phase)
0.7103	Intermediate Similarity	NPD164	Approved
0.7097	Intermediate Similarity	NPD225	Approved
0.7097	Intermediate Similarity	NPD227	Approved
0.7091	Intermediate Similarity	NPD5240	Approved
0.7091	Intermediate Similarity	NPD5236	Approved
0.7091	Intermediate Similarity	NPD5235	Approved
0.7091	Intermediate Similarity	NPD5237	Approved
0.7091	Intermediate Similarity	NPD5239	Approved
0.708	Intermediate Similarity	NPD690	Clinical (unspecified phase)
0.7075	Intermediate Similarity	NPD4189	Approved
0.7075	Intermediate Similarity	NPD4188	Approved
0.7048	Intermediate Similarity	NPD2066	Phase 3
0.7027	Intermediate Similarity	NPD2201	Approved
0.7021	Intermediate Similarity	NPD9490	Approved
0.7018	Intermediate Similarity	NPD4198	Discontinued
0.7009	Intermediate Similarity	NPD5738	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD800	Approved
0.6991	Remote Similarity	NPD1241	Discontinued
0.6972	Remote Similarity	NPD6685	Approved
0.6952	Remote Similarity	NPD9495	Approved
0.6949	Remote Similarity	NPD3496	Discontinued
0.6944	Remote Similarity	NPD3048	Approved
0.6944	Remote Similarity	NPD3046	Approved
0.6944	Remote Similarity	NPD3047	Approved
0.6942	Remote Similarity	NPD2797	Approved
0.6931	Remote Similarity	NPD1090	Approved
0.6931	Remote Similarity	NPD1089	Approved
0.6931	Remote Similarity	NPD1086	Approved
0.693	Remote Similarity	NPD2629	Approved
0.6907	Remote Similarity	NPD9491	Approved
0.6903	Remote Similarity	NPD6858	Approved
0.6903	Remote Similarity	NPD7094	Approved
0.6893	Remote Similarity	NPD1202	Approved
0.6891	Remote Similarity	NPD422	Phase 1
0.6875	Remote Similarity	NPD226	Approved
0.6869	Remote Similarity	NPD9257	Approved
0.6869	Remote Similarity	NPD9259	Approved
0.6864	Remote Similarity	NPD4626	Approved
0.6847	Remote Similarity	NPD2684	Approved
0.6833	Remote Similarity	NPD6637	Approved
0.6832	Remote Similarity	NPD5346	Phase 2
0.6832	Remote Similarity	NPD5347	Phase 2
0.6827	Remote Similarity	NPD1693	Approved
0.6818	Remote Similarity	NPD3524	Approved
0.6818	Remote Similarity	NPD2559	Approved
0.6818	Remote Similarity	NPD2551	Approved
0.6818	Remote Similarity	NPD3526	Approved
0.6803	Remote Similarity	NPD3267	Approved
0.6803	Remote Similarity	NPD3266	Approved
0.68	Remote Similarity	NPD4793	Discontinued
0.6796	Remote Similarity	NPD1088	Approved
0.6789	Remote Similarity	NPD1237	Approved
0.678	Remote Similarity	NPD5585	Approved
0.6774	Remote Similarity	NPD6832	Phase 2
0.6757	Remote Similarity	NPD290	Approved
0.6752	Remote Similarity	NPD2347	Approved
0.675	Remote Similarity	NPD6287	Discontinued
0.6748	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6733	Remote Similarity	NPD531	Approved
0.6731	Remote Similarity	NPD1066	Discontinued
0.6731	Remote Similarity	NPD1563	Approved
0.6723	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6699	Remote Similarity	NPD1239	Approved
0.6697	Remote Similarity	NPD1931	Clinical (unspecified phase)
0.6697	Remote Similarity	NPD5765	Approved
0.6697	Remote Similarity	NPD1930	Approved
0.6697	Remote Similarity	NPD1929	Approved
0.6696	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6695	Remote Similarity	NPD1894	Discontinued
0.6695	Remote Similarity	NPD9545	Approved
0.6667	Remote Similarity	NPD812	Approved
0.6667	Remote Similarity	NPD6049	Phase 2
0.6667	Remote Similarity	NPD9493	Approved
0.6667	Remote Similarity	NPD3847	Discontinued
0.6667	Remote Similarity	NPD811	Approved
0.6667	Remote Similarity	NPD3268	Approved
0.6667	Remote Similarity	NPD6048	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD810	Approved
0.6641	Remote Similarity	NPD5124	Phase 1
0.6641	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6637	Remote Similarity	NPD5451	Approved
0.6637	Remote Similarity	NPD1756	Approved
0.6637	Remote Similarity	NPD1752	Approved
0.6632	Remote Similarity	NPD9294	Approved
0.6612	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6609	Remote Similarity	NPD7843	Approved
0.6604	Remote Similarity	NPD2860	Approved
0.6604	Remote Similarity	NPD2859	Approved
0.6602	Remote Similarity	NPD9258	Approved
0.6602	Remote Similarity	NPD9256	Approved
0.6587	Remote Similarity	NPD5454	Clinical (unspecified phase)
0.6585	Remote Similarity	NPD5667	Approved
0.6585	Remote Similarity	NPD2199	Approved
0.6585	Remote Similarity	NPD2198	Approved
0.6583	Remote Similarity	NPD1778	Approved
0.6583	Remote Similarity	NPD17	Approved
0.6557	Remote Similarity	NPD1877	Discontinued
0.6552	Remote Similarity	NPD2650	Approved
0.6552	Remote Similarity	NPD2652	Approved
0.6542	Remote Similarity	NPD1564	Approved
0.6542	Remote Similarity	NPD1566	Phase 3
0.6542	Remote Similarity	NPD1565	Approved
0.6535	Remote Similarity	NPD6798	Discontinued
0.6525	Remote Similarity	NPD4576	Approved
0.6525	Remote Similarity	NPD4574	Approved
0.6522	Remote Similarity	NPD1139	Approved
0.6522	Remote Similarity	NPD1137	Approved
0.6522	Remote Similarity	NPD6912	Phase 3
0.6522	Remote Similarity	NPD4572	Approved
0.6522	Remote Similarity	NPD4573	Approved
0.6522	Remote Similarity	NPD4571	Approved
0.6518	Remote Similarity	NPD968	Approved
0.6509	Remote Similarity	NPD2933	Approved
0.6509	Remote Similarity	NPD688	Clinical (unspecified phase)
0.6509	Remote Similarity	NPD2934	Approved
0.6508	Remote Similarity	NPD1008	Clinical (unspecified phase)
0.6504	Remote Similarity	NPD4359	Approved
0.6491	Remote Similarity	NPD4233	Approved
0.6491	Remote Similarity	NPD3646	Clinical (unspecified phase)
0.6491	Remote Similarity	NPD4234	Approved
0.6489	Remote Similarity	NPD7033	Discontinued
0.6484	Remote Similarity	NPD6233	Phase 2
0.648	Remote Similarity	NPD1019	Discontinued
0.6475	Remote Similarity	NPD1281	Approved
0.6475	Remote Similarity	NPD4480	Approved
0.6475	Remote Similarity	NPD1611	Approved
0.6466	Remote Similarity	NPD2497	Approved
0.6466	Remote Similarity	NPD1138	Approved
0.6466	Remote Similarity	NPD2496	Approved
0.6466	Remote Similarity	NPD821	Approved
0.6466	Remote Similarity	NPD2607	Approved
0.6457	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6457	Remote Similarity	NPD7008	Discontinued
0.6455	Remote Similarity	NPD1932	Approved
0.6452	Remote Similarity	NPD3225	Approved
0.6446	Remote Similarity	NPD5126	Approved
0.6446	Remote Similarity	NPD5125	Phase 3
0.6446	Remote Similarity	NPD5306	Approved
0.6446	Remote Similarity	NPD5305	Approved
0.6441	Remote Similarity	NPD2557	Approved
0.6441	Remote Similarity	NPD7157	Approved
0.6434	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6434	Remote Similarity	NPD4140	Approved
0.6434	Remote Similarity	NPD4307	Phase 2
0.6429	Remote Similarity	NPD1507	Clinical (unspecified phase)
0.6423	Remote Similarity	NPD9717	Approved
0.6423	Remote Similarity	NPD3972	Approved
0.6423	Remote Similarity	NPD1608	Approved
0.6422	Remote Similarity	NPD3020	Approved
0.6418	Remote Similarity	NPD1652	Phase 2
0.6417	Remote Similarity	NPD7741	Discontinued
0.6415	Remote Similarity	NPD720	Approved
0.6415	Remote Similarity	NPD845	Approved
0.6415	Remote Similarity	NPD719	Approved
0.6412	Remote Similarity	NPD2569	Approved
0.6412	Remote Similarity	NPD2567	Approved
0.641	Remote Similarity	NPD5283	Phase 1
0.6406	Remote Similarity	NPD3374	Clinical (unspecified phase)
0.6406	Remote Similarity	NPD1296	Phase 2
0.6406	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.64	Remote Similarity	NPD6362	Approved
0.6396	Remote Similarity	NPD9261	Approved
0.6396	Remote Similarity	NPD5700	Clinical (unspecified phase)

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