NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	266.09
Volume:	282.198
LogP:	4.011
LogD:	2.829
LogS:	-4.629
# Rotatable Bonds:	2
TPSA:	39.44
# H-Bond Aceptor:	3
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.709
Synthetic Accessibility Score:	2.193
Fsp3:	0.118
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.603
MDCK Permeability:	1.2181880265416112e-05
Pgp-inhibitor:	0.997
Pgp-substrate:	0.274
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.041
30% Bioavailability (F30%):	0.915

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.03
Plasma Protein Binding (PPB):	97.84033966064453%
Volume Distribution (VD):	0.476
Pgp-substrate:	1.843109369277954%

ADMET: Metabolism

CYP1A2-inhibitor:	0.97
CYP1A2-substrate:	0.804
CYP2C19-inhibitor:	0.874
CYP2C19-substrate:	0.093
CYP2C9-inhibitor:	0.607
CYP2C9-substrate:	0.88
CYP2D6-inhibitor:	0.049
CYP2D6-substrate:	0.889
CYP3A4-inhibitor:	0.291
CYP3A4-substrate:	0.326

ADMET: Excretion

Clearance (CL):	2.963
Half-life (T1/2):	0.116

ADMET: Toxicity

hERG Blockers:	0.118
Human Hepatotoxicity (H-HT):	0.092
Drug-inuced Liver Injury (DILI):	0.899
AMES Toxicity:	0.371
Rat Oral Acute Toxicity:	0.136
Maximum Recommended Daily Dose:	0.119
Skin Sensitization:	0.072
Carcinogencity:	0.367
Eye Corrosion:	0.003
Eye Irritation:	0.84
Respiratory Toxicity:	0.154

Download Data

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

Natural Product: NPC5472

Natural Product ID:	NPC5472
*Common Name:**	Dracorhodin
IUPAC Name:	5-methoxy-6-methyl-2-phenylchromen-7-one
Synonyms:	Dracorhodin
Standard InCHIKey:	UCZJPQIEFFTIEV-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C17H14O3/c1-11-14(18)10-16-13(17(11)19-2)8-9-15(20-16)12-6-4-3-5-7-12/h3-10H,1-2H3
SMILES:	Cc1c(=O)cc2-c(ccc(c3ccccc3)o2)c1OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL486600
PubChem CID:	69509
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0002585] O-methylated flavonoids [CHEMONTID:0002590] 5-O-methylated flavonoids

*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
NPO2685	Sanguis draconis	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[HerDing]
NPO31251	Semen entadae	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[HerDing]
NPO495	Daemonorops draco	Species	Arecaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO2685	Sanguis draconis	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[TCMID]
NPO5184	Semen entadae phaseoloidis	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[TCMID]
NPO495	Daemonorops draco	Species	Arecaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO495	Daemonorops draco	Species	Arecaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO495	Daemonorops draco	Species	Arecaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO495	Daemonorops draco	Species	Arecaceae	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
Others	4

Activity Type	# Activity
Organism	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	Activity	=	50.0	ug ml-1	PMID[565936]
NPT173	Organism	Klebsiella pneumoniae	Klebsiella pneumoniae	Activity	=	100.0	ug ml-1	PMID[565936]
NPT602	Organism	Mycobacterium smegmatis	Mycobacterium smegmatis	Activity	=	25.0	ug ml-1	PMID[565936]
NPT20	Organism	Candida albicans	Candida albicans	Activity	=	25.0	ug ml-1	PMID[565936]

☑ 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 NPC5472 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	520
0.1-0.2	2077
0.2-0.3	5784
0.3-0.4	12362
0.4-0.5	4581
0.5-0.6	5240
0.6-0.7	5929
0.7-0.8	4395
0.8-0.85	1231
0.85-0.9	541
0.9-0.95	36
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8387	Intermediate Similarity	NPC173443
0.837	Intermediate Similarity	NPC96625
0.8229	Intermediate Similarity	NPC23453
0.8224	Intermediate Similarity	NPC471616
0.8211	Intermediate Similarity	NPC119631
0.8173	Intermediate Similarity	NPC273837
0.8172	Intermediate Similarity	NPC89377
0.8172	Intermediate Similarity	NPC169050
0.8172	Intermediate Similarity	NPC286608
0.8152	Intermediate Similarity	NPC58616
0.8152	Intermediate Similarity	NPC53299
0.8131	Intermediate Similarity	NPC474408
0.8085	Intermediate Similarity	NPC304760
0.8037	Intermediate Similarity	NPC196075
0.8022	Intermediate Similarity	NPC99240
0.8019	Intermediate Similarity	NPC212415
0.8	Intermediate Similarity	NPC220893
0.8	Intermediate Similarity	NPC98911
0.8	Intermediate Similarity	NPC472318
0.7963	Intermediate Similarity	NPC228936
0.7961	Intermediate Similarity	NPC209632
0.7944	Intermediate Similarity	NPC13784
0.7941	Intermediate Similarity	NPC301943
0.7941	Intermediate Similarity	NPC474365
0.7941	Intermediate Similarity	NPC234305
0.7925	Intermediate Similarity	NPC474157
0.7912	Intermediate Similarity	NPC165212
0.79	Intermediate Similarity	NPC175298
0.7864	Intermediate Similarity	NPC85977
0.7864	Intermediate Similarity	NPC114594
0.7864	Intermediate Similarity	NPC109637
0.7826	Intermediate Similarity	NPC106313
0.7822	Intermediate Similarity	NPC325497
0.7818	Intermediate Similarity	NPC190298
0.78	Intermediate Similarity	NPC276775
0.78	Intermediate Similarity	NPC92754
0.78	Intermediate Similarity	NPC249912
0.7778	Intermediate Similarity	NPC161611
0.7778	Intermediate Similarity	NPC130398
0.7768	Intermediate Similarity	NPC43435
0.7736	Intermediate Similarity	NPC269023
0.7736	Intermediate Similarity	NPC474364
0.7736	Intermediate Similarity	NPC40178
0.7736	Intermediate Similarity	NPC99846
0.7732	Intermediate Similarity	NPC240108
0.7732	Intermediate Similarity	NPC213156
0.7727	Intermediate Similarity	NPC135730
0.7723	Intermediate Similarity	NPC225060
0.7723	Intermediate Similarity	NPC78701
0.7723	Intermediate Similarity	NPC35448
0.7717	Intermediate Similarity	NPC71795
0.7714	Intermediate Similarity	NPC475203
0.7714	Intermediate Similarity	NPC474376
0.7714	Intermediate Similarity	NPC472316
0.7714	Intermediate Similarity	NPC472315
0.7706	Intermediate Similarity	NPC477411
0.7706	Intermediate Similarity	NPC308744
0.77	Intermediate Similarity	NPC12695
0.767	Intermediate Similarity	NPC84325
0.7664	Intermediate Similarity	NPC149545
0.7653	Intermediate Similarity	NPC476484
0.7647	Intermediate Similarity	NPC146351
0.7647	Intermediate Similarity	NPC118343
0.7642	Intermediate Similarity	NPC47536
0.7642	Intermediate Similarity	NPC470391
0.7636	Intermediate Similarity	NPC114144
0.7636	Intermediate Similarity	NPC210092
0.7624	Intermediate Similarity	NPC103048
0.7619	Intermediate Similarity	NPC127676
0.7615	Intermediate Similarity	NPC272524
0.7596	Intermediate Similarity	NPC298224
0.7596	Intermediate Similarity	NPC179686
0.7596	Intermediate Similarity	NPC60679
0.7593	Intermediate Similarity	NPC291799
0.7573	Intermediate Similarity	NPC70624
0.7573	Intermediate Similarity	NPC42211
0.7573	Intermediate Similarity	NPC13755
0.7568	Intermediate Similarity	NPC226093
0.7568	Intermediate Similarity	NPC216387
0.7553	Intermediate Similarity	NPC324835
0.7553	Intermediate Similarity	NPC308619
0.7553	Intermediate Similarity	NPC127491
0.7547	Intermediate Similarity	NPC30594
0.7547	Intermediate Similarity	NPC477251
0.7547	Intermediate Similarity	NPC326447
0.7547	Intermediate Similarity	NPC37622
0.7547	Intermediate Similarity	NPC136962
0.7544	Intermediate Similarity	NPC289432
0.7544	Intermediate Similarity	NPC988
0.7524	Intermediate Similarity	NPC171831
0.7524	Intermediate Similarity	NPC280616
0.7524	Intermediate Similarity	NPC242913
0.7524	Intermediate Similarity	NPC38209
0.75	Intermediate Similarity	NPC33717
0.7478	Intermediate Similarity	NPC144547
0.7477	Intermediate Similarity	NPC474685
0.7477	Intermediate Similarity	NPC157473
0.7477	Intermediate Similarity	NPC277788
0.7477	Intermediate Similarity	NPC474095
0.7477	Intermediate Similarity	NPC151530
0.7476	Intermediate Similarity	NPC203925
0.7476	Intermediate Similarity	NPC474308
0.7455	Intermediate Similarity	NPC265002
0.7455	Intermediate Similarity	NPC474176
0.7453	Intermediate Similarity	NPC227255
0.7453	Intermediate Similarity	NPC139891
0.7453	Intermediate Similarity	NPC238115
0.7453	Intermediate Similarity	NPC128730
0.7453	Intermediate Similarity	NPC269457
0.7451	Intermediate Similarity	NPC278228
0.7451	Intermediate Similarity	NPC270654
0.7451	Intermediate Similarity	NPC325499
0.7431	Intermediate Similarity	NPC210089
0.7429	Intermediate Similarity	NPC91820
0.7429	Intermediate Similarity	NPC82426
0.7419	Intermediate Similarity	NPC121800
0.7407	Intermediate Similarity	NPC206341
0.7407	Intermediate Similarity	NPC469636
0.7407	Intermediate Similarity	NPC281604
0.74	Intermediate Similarity	NPC321956
0.74	Intermediate Similarity	NPC77273
0.7391	Intermediate Similarity	NPC31314
0.7391	Intermediate Similarity	NPC77000
0.7391	Intermediate Similarity	NPC193193
0.7391	Intermediate Similarity	NPC238861
0.7391	Intermediate Similarity	NPC168050
0.7391	Intermediate Similarity	NPC232958
0.7387	Intermediate Similarity	NPC90903
0.7387	Intermediate Similarity	NPC87069
0.7383	Intermediate Similarity	NPC176971
0.7383	Intermediate Similarity	NPC37115
0.7379	Intermediate Similarity	NPC145052
0.7379	Intermediate Similarity	NPC476120
0.7374	Intermediate Similarity	NPC108026
0.7374	Intermediate Similarity	NPC177844
0.7374	Intermediate Similarity	NPC8002
0.7374	Intermediate Similarity	NPC99886
0.7374	Intermediate Similarity	NPC259134
0.7368	Intermediate Similarity	NPC152159
0.7364	Intermediate Similarity	NPC477250
0.7364	Intermediate Similarity	NPC23332
0.7364	Intermediate Similarity	NPC234376
0.7358	Intermediate Similarity	NPC2518
0.7358	Intermediate Similarity	NPC269644
0.7345	Intermediate Similarity	NPC128633
0.7345	Intermediate Similarity	NPC268317
0.7345	Intermediate Similarity	NPC19290
0.734	Intermediate Similarity	NPC89950
0.7333	Intermediate Similarity	NPC188895
0.7321	Intermediate Similarity	NPC87563
0.7312	Intermediate Similarity	NPC167577
0.7312	Intermediate Similarity	NPC170484
0.7312	Intermediate Similarity	NPC78517
0.7308	Intermediate Similarity	NPC476042
0.7304	Intermediate Similarity	NPC54243
0.73	Intermediate Similarity	NPC71853
0.7297	Intermediate Similarity	NPC128368
0.7292	Intermediate Similarity	NPC95429
0.729	Intermediate Similarity	NPC473855
0.729	Intermediate Similarity	NPC288760
0.7283	Intermediate Similarity	NPC3672
0.7283	Intermediate Similarity	NPC287790
0.7281	Intermediate Similarity	NPC45104
0.7281	Intermediate Similarity	NPC469954
0.7273	Intermediate Similarity	NPC476003
0.7273	Intermediate Similarity	NPC473809
0.7273	Intermediate Similarity	NPC243355
0.7273	Intermediate Similarity	NPC183648
0.7273	Intermediate Similarity	NPC141068
0.7264	Intermediate Similarity	NPC135784
0.7264	Intermediate Similarity	NPC304638
0.7263	Intermediate Similarity	NPC323103
0.7263	Intermediate Similarity	NPC103387
0.7257	Intermediate Similarity	NPC149691
0.7257	Intermediate Similarity	NPC296526
0.7257	Intermediate Similarity	NPC473507
0.7255	Intermediate Similarity	NPC471581
0.7255	Intermediate Similarity	NPC473347
0.7248	Intermediate Similarity	NPC265407
0.7248	Intermediate Similarity	NPC469511
0.7248	Intermediate Similarity	NPC83628
0.7248	Intermediate Similarity	NPC17417
0.7248	Intermediate Similarity	NPC10251
0.7241	Intermediate Similarity	NPC474223
0.7241	Intermediate Similarity	NPC474874
0.7241	Intermediate Similarity	NPC475827
0.7238	Intermediate Similarity	NPC107101
0.7238	Intermediate Similarity	NPC253746
0.7238	Intermediate Similarity	NPC112552
0.7234	Intermediate Similarity	NPC328178
0.7232	Intermediate Similarity	NPC279916
0.7227	Intermediate Similarity	NPC98509
0.7222	Intermediate Similarity	NPC1065
0.7222	Intermediate Similarity	NPC119271
0.7222	Intermediate Similarity	NPC51174
0.7217	Intermediate Similarity	NPC32298
0.7217	Intermediate Similarity	NPC265547
0.7217	Intermediate Similarity	NPC96705
0.7212	Intermediate Similarity	NPC475954
0.7212	Intermediate Similarity	NPC179411

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 NPC5472 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	484
0.1-0.2	1016
0.2-0.3	1695
0.3-0.4	2815
0.4-0.5	1693
0.5-0.6	1004
0.6-0.7	307
0.7-0.8	102
0.8-0.85	25
0.85-0.9	9
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8172	Intermediate Similarity	NPD1282	Approved
0.8019	Intermediate Similarity	NPD1609	Clinical (unspecified phase)
0.7706	Intermediate Similarity	NPD1241	Discontinued
0.7647	Intermediate Similarity	NPD1238	Approved
0.7547	Intermediate Similarity	NPD3134	Approved
0.7524	Intermediate Similarity	NPD5909	Discontinued
0.7453	Intermediate Similarity	NPD9697	Approved
0.7391	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.7315	Intermediate Similarity	NPD1358	Approved
0.7273	Intermediate Similarity	NPD2181	Clinical (unspecified phase)
0.7248	Intermediate Similarity	NPD2182	Approved
0.7196	Intermediate Similarity	NPD164	Approved
0.7182	Intermediate Similarity	NPD2067	Discontinued
0.7168	Intermediate Similarity	NPD690	Clinical (unspecified phase)
0.7167	Intermediate Similarity	NPD3267	Approved
0.7167	Intermediate Similarity	NPD3266	Approved
0.7143	Intermediate Similarity	NPD5535	Approved
0.713	Intermediate Similarity	NPD5536	Phase 2
0.7075	Intermediate Similarity	NPD2550	Approved
0.7075	Intermediate Similarity	NPD2552	Approved
0.7075	Intermediate Similarity	NPD2555	Approved
0.7075	Intermediate Similarity	NPD2553	Approved
0.7075	Intermediate Similarity	NPD2549	Approved
0.7075	Intermediate Similarity	NPD2558	Approved
0.7054	Intermediate Similarity	NPD969	Suspended
0.7048	Intermediate Similarity	NPD5926	Approved
0.7027	Intermediate Similarity	NPD5235	Approved
0.7027	Intermediate Similarity	NPD5237	Approved
0.7027	Intermediate Similarity	NPD5236	Approved
0.7027	Intermediate Similarity	NPD5239	Approved
0.7027	Intermediate Similarity	NPD5240	Approved
0.7027	Intermediate Similarity	NPD5451	Approved
0.7025	Intermediate Similarity	NPD2797	Approved
0.7009	Intermediate Similarity	NPD4189	Approved
0.7009	Intermediate Similarity	NPD4188	Approved
0.7	Intermediate Similarity	NPD290	Approved
0.699	Remote Similarity	NPD1202	Approved
0.6975	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.697	Remote Similarity	NPD9257	Approved
0.697	Remote Similarity	NPD9259	Approved
0.6964	Remote Similarity	NPD2201	Approved
0.6957	Remote Similarity	NPD4198	Discontinued
0.6942	Remote Similarity	NPD3225	Approved
0.6937	Remote Similarity	NPD2684	Approved
0.6917	Remote Similarity	NPD3972	Approved
0.6915	Remote Similarity	NPD9294	Approved
0.6909	Remote Similarity	NPD968	Approved
0.6909	Remote Similarity	NPD3526	Approved
0.6909	Remote Similarity	NPD3524	Approved
0.6897	Remote Similarity	NPD9493	Approved
0.6897	Remote Similarity	NPD694	Clinical (unspecified phase)
0.6881	Remote Similarity	NPD3048	Approved
0.6881	Remote Similarity	NPD3047	Approved
0.6881	Remote Similarity	NPD3046	Approved
0.6881	Remote Similarity	NPD1237	Approved
0.688	Remote Similarity	NPD3268	Approved
0.6864	Remote Similarity	NPD5585	Approved
0.6864	Remote Similarity	NPD5691	Approved
0.6833	Remote Similarity	NPD422	Phase 1
0.6833	Remote Similarity	NPD6287	Discontinued
0.6829	Remote Similarity	NPD2798	Approved
0.6827	Remote Similarity	NPD5122	Clinical (unspecified phase)
0.6803	Remote Similarity	NPD1876	Approved
0.6789	Remote Similarity	NPD6647	Phase 2
0.678	Remote Similarity	NPD1894	Discontinued
0.678	Remote Similarity	NPD9545	Approved
0.6762	Remote Similarity	NPD2934	Approved
0.6762	Remote Similarity	NPD2933	Approved
0.6757	Remote Similarity	NPD2559	Approved
0.6757	Remote Similarity	NPD2551	Approved
0.675	Remote Similarity	NPD3496	Discontinued
0.6723	Remote Similarity	NPD1651	Approved
0.6721	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.672	Remote Similarity	NPD6832	Phase 2
0.6699	Remote Similarity	NPD9256	Approved
0.6699	Remote Similarity	NPD9258	Approved
0.6698	Remote Similarity	NPD1989	Approved
0.6698	Remote Similarity	NPD2860	Approved
0.6698	Remote Similarity	NPD2859	Approved
0.6696	Remote Similarity	NPD7843	Approved
0.6694	Remote Similarity	NPD2788	Approved
0.6667	Remote Similarity	NPD4626	Approved
0.6667	Remote Similarity	NPD2066	Phase 3
0.6641	Remote Similarity	NPD4307	Phase 2
0.6641	Remote Similarity	NPD2796	Approved
0.6639	Remote Similarity	NPD1548	Phase 1
0.6639	Remote Similarity	NPD9717	Approved
0.6638	Remote Similarity	NPD5283	Phase 1
0.6637	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6633	Remote Similarity	NPD9250	Approved
0.6614	Remote Similarity	NPD2313	Discontinued
0.6612	Remote Similarity	NPD3847	Discontinued
0.6609	Remote Similarity	NPD4573	Approved
0.6609	Remote Similarity	NPD4572	Approved
0.6609	Remote Similarity	NPD4571	Approved
0.6607	Remote Similarity	NPD811	Approved
0.6607	Remote Similarity	NPD812	Approved
0.6607	Remote Similarity	NPD810	Approved
0.6602	Remote Similarity	NPD689	Discontinued
0.6598	Remote Similarity	NPD9490	Approved
0.6589	Remote Similarity	NPD1933	Approved
0.6587	Remote Similarity	NPD2985	Phase 3
0.6587	Remote Similarity	NPD1008	Clinical (unspecified phase)
0.6585	Remote Similarity	NPD4359	Approved
0.6574	Remote Similarity	NPD9495	Approved
0.6565	Remote Similarity	NPD3748	Approved
0.656	Remote Similarity	NPD1019	Discontinued
0.6552	Remote Similarity	NPD821	Approved
0.6538	Remote Similarity	NPD3672	Approved
0.6538	Remote Similarity	NPD3673	Approved
0.6535	Remote Similarity	NPD111	Approved
0.6535	Remote Similarity	NPD6039	Approved
0.6532	Remote Similarity	NPD2198	Approved
0.6532	Remote Similarity	NPD2199	Approved
0.6529	Remote Similarity	NPD17	Approved
0.6529	Remote Similarity	NPD1778	Approved
0.6526	Remote Similarity	NPD9716	Approved
0.6525	Remote Similarity	NPD6671	Approved
0.6525	Remote Similarity	NPD2557	Approved
0.6525	Remote Similarity	NPD7157	Approved
0.6514	Remote Similarity	NPD7798	Approved
0.6514	Remote Similarity	NPD3020	Approved
0.6512	Remote Similarity	NPD3142	Approved
0.6512	Remote Similarity	NPD3140	Approved
0.6504	Remote Similarity	NPD1877	Discontinued
0.65	Remote Similarity	NPD7741	Discontinued
0.65	Remote Similarity	NPD6580	Approved
0.65	Remote Similarity	NPD3971	Phase 1
0.65	Remote Similarity	NPD9491	Approved
0.65	Remote Similarity	NPD6581	Approved
0.6496	Remote Similarity	NPD6010	Discontinued
0.6495	Remote Similarity	NPD227	Approved
0.6495	Remote Similarity	NPD225	Approved
0.6486	Remote Similarity	NPD1929	Approved
0.6486	Remote Similarity	NPD9261	Approved
0.6486	Remote Similarity	NPD1930	Approved
0.6486	Remote Similarity	NPD1931	Clinical (unspecified phase)
0.648	Remote Similarity	NPD1203	Approved
0.6475	Remote Similarity	NPD7457	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD5292	Approved
0.6471	Remote Similarity	NPD5291	Approved
0.6471	Remote Similarity	NPD3596	Phase 2
0.6466	Remote Similarity	NPD1137	Approved
0.6466	Remote Similarity	NPD1139	Approved
0.6466	Remote Similarity	NPD228	Approved
0.6462	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6455	Remote Similarity	NPD3028	Approved
0.6449	Remote Similarity	NPD9260	Approved
0.6446	Remote Similarity	NPD6382	Discontinued
0.6446	Remote Similarity	NPD6830	Clinical (unspecified phase)
0.6441	Remote Similarity	NPD2629	Approved
0.6439	Remote Similarity	NPD4308	Phase 3
0.6435	Remote Similarity	NPD551	Approved
0.6435	Remote Similarity	NPD550	Approved
0.6434	Remote Similarity	NPD7713	Phase 3
0.6434	Remote Similarity	NPD6233	Phase 2
0.6423	Remote Similarity	NPD1281	Approved
0.6417	Remote Similarity	NPD2347	Approved
0.641	Remote Similarity	NPD2496	Approved
0.641	Remote Similarity	NPD6858	Approved
0.641	Remote Similarity	NPD2497	Approved
0.641	Remote Similarity	NPD1138	Approved
0.641	Remote Similarity	NPD7094	Approved
0.6408	Remote Similarity	NPD1087	Approved
0.6408	Remote Similarity	NPD650	Approved
0.6406	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6406	Remote Similarity	NPD5454	Clinical (unspecified phase)
0.64	Remote Similarity	NPD5667	Approved
0.6393	Remote Similarity	NPD6516	Phase 2
0.6393	Remote Similarity	NPD2423	Clinical (unspecified phase)
0.6393	Remote Similarity	NPD5126	Approved
0.6393	Remote Similarity	NPD5125	Phase 3
0.6393	Remote Similarity	NPD5846	Approved
0.6387	Remote Similarity	NPD6387	Discontinued
0.6385	Remote Similarity	NPD1240	Approved
0.6371	Remote Similarity	NPD1608	Approved
0.6364	Remote Similarity	NPD1507	Clinical (unspecified phase)
0.6357	Remote Similarity	NPD1296	Phase 2
0.6357	Remote Similarity	NPD6798	Discontinued
0.6357	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6356	Remote Similarity	NPD2988	Approved
0.6356	Remote Similarity	NPD592	Approved
0.6356	Remote Similarity	NPD2991	Approved
0.6356	Remote Similarity	NPD594	Approved
0.6355	Remote Similarity	NPD845	Approved
0.6336	Remote Similarity	NPD5124	Phase 1
0.6336	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6336	Remote Similarity	NPD4340	Discontinued
0.6324	Remote Similarity	NPD3750	Approved
0.6321	Remote Similarity	NPD9365	Approved
0.6321	Remote Similarity	NPD7609	Phase 3
0.632	Remote Similarity	NPD6582	Phase 2
0.632	Remote Similarity	NPD6583	Phase 3
0.632	Remote Similarity	NPD4749	Approved
0.632	Remote Similarity	NPD5327	Phase 3
0.6316	Remote Similarity	NPD7033	Discontinued
0.6316	Remote Similarity	NPD1510	Phase 2
0.6311	Remote Similarity	NPD3443	Approved
0.6311	Remote Similarity	NPD3049	Approved
0.6311	Remote Similarity	NPD3445	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