NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	204.04
Volume:	201.042
LogP:	1.836
LogD:	1.408
LogS:	-3.828
# Rotatable Bonds:	0
TPSA:	71.44
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.505
Synthetic Accessibility Score:	2.998
Fsp3:	0.182
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	2

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.648
MDCK Permeability:	2.3586395400343463e-05
Pgp-inhibitor:	0.013
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.004
30% Bioavailability (F30%):	0.159

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.248
Plasma Protein Binding (PPB):	95.67630004882812%
Volume Distribution (VD):	0.439
Pgp-substrate:	1.445502758026123%

ADMET: Metabolism

CYP1A2-inhibitor:	0.939
CYP1A2-substrate:	0.529
CYP2C19-inhibitor:	0.179
CYP2C19-substrate:	0.066
CYP2C9-inhibitor:	0.32
CYP2C9-substrate:	0.597
CYP2D6-inhibitor:	0.462
CYP2D6-substrate:	0.237
CYP3A4-inhibitor:	0.312
CYP3A4-substrate:	0.173

ADMET: Excretion

Clearance (CL):	1.718
Half-life (T1/2):	0.323

ADMET: Toxicity

hERG Blockers:	0.011
Human Hepatotoxicity (H-HT):	0.119
Drug-inuced Liver Injury (DILI):	0.934
AMES Toxicity:	0.791
Rat Oral Acute Toxicity:	0.138
Maximum Recommended Daily Dose:	0.018
Skin Sensitization:	0.546
Carcinogencity:	0.516
Eye Corrosion:	0.021
Eye Irritation:	0.689
Respiratory Toxicity:	0.233

Download Data

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

Natural Product: NPC310540

Natural Product ID:	NPC310540
*Common Name:**	Droserone
IUPAC Name:	n.a.
Synonyms:	Droserone
Standard InCHIKey:	CQDXJBJBEQPBEM-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C11H8O4/c1-5-9(13)6-3-2-4-7(12)8(6)11(15)10(5)14/h2-4,12,14H,1H3
SMILES:	CC1=C(O)C(=O)c2c(C1=O)cccc2O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1915212
PubChem CID:	NA
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000023] Naphthalenes [CHEMONTID:0000153] Naphthoquinones

*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
NPO6969	Triphyophyllum peltatum	Species	Dioncophyllaceae	Eukaryota	n.a.	root	n.a.	DOI[10.1007/s004360050318]
NPO6969	Triphyophyllum peltatum	Species	Dioncophyllaceae	Eukaryota	n.a.	stem	n.a.	DOI[10.1007/s004360050318]
NPO6969	Triphyophyllum peltatum	Species	Dioncophyllaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22019229]
NPO6969	Triphyophyllum peltatum	Species	Dioncophyllaceae	Eukaryota	n.a.	stem	n.a.	PMID[9371362]
NPO6969	Triphyophyllum peltatum	Species	Dioncophyllaceae	Eukaryota	n.a.	root	n.a.	PMID[9371362]
NPO3062	Drosera whittakeri	Species	Droseraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO3062	Drosera whittakeri	Species	Droseraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11416	Helleborus torquatus	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6969	Triphyophyllum peltatum	Species	Dioncophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11416	Helleborus torquatus	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3062	Drosera whittakeri	Species	Droseraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6969	Triphyophyllum peltatum	Species	Dioncophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1494	Nepenthes gracilis	Species	Nepenthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8761	Gelidium amansii	Species	Gelidiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1851	Monanthotaxis cauliflora	Species	Annonaceae	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

Activity Type	# Activity
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	EC50	>	100000.0	nM	PMID[509301]

☑ 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 NPC310540 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	309
0.1-0.2	1608
0.2-0.3	4187
0.3-0.4	10897
0.4-0.5	8124
0.5-0.6	6429
0.6-0.7	8326
0.7-0.8	2445
0.8-0.85	267
0.85-0.9	80
0.9-0.95	19
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
0.9669	High Similarity	NPC237225
0.9667	High Similarity	NPC231774
0.9573	High Similarity	NPC285829
0.9573	High Similarity	NPC206778
0.9504	High Similarity	NPC51037
0.9504	High Similarity	NPC1991
0.9355	High Similarity	NPC198305
0.9344	High Similarity	NPC306765
0.9333	High Similarity	NPC307174
0.9286	High Similarity	NPC171968
0.9274	High Similarity	NPC278928
0.9231	High Similarity	NPC108288
0.9194	High Similarity	NPC165257
0.9187	High Similarity	NPC3224
0.916	High Similarity	NPC232178
0.9127	High Similarity	NPC205360
0.9098	High Similarity	NPC375356
0.9055	High Similarity	NPC309430
0.9048	High Similarity	NPC117609
0.9032	High Similarity	NPC96915
0.9016	High Similarity	NPC300274
0.8968	High Similarity	NPC146647
0.8968	High Similarity	NPC34414
0.8952	High Similarity	NPC103540
0.8931	High Similarity	NPC173980
0.8906	High Similarity	NPC110609
0.8906	High Similarity	NPC246693
0.8906	High Similarity	NPC242358
0.8898	High Similarity	NPC55949
0.8898	High Similarity	NPC136588
0.8898	High Similarity	NPC199253
0.8889	High Similarity	NPC282923
0.8871	High Similarity	NPC234890
0.8871	High Similarity	NPC142956
0.8871	High Similarity	NPC74507
0.8837	High Similarity	NPC254603
0.8828	High Similarity	NPC205992
0.8828	High Similarity	NPC244699
0.8824	High Similarity	NPC240163
0.8824	High Similarity	NPC161304
0.8819	High Similarity	NPC99731
0.881	High Similarity	NPC471530
0.879	High Similarity	NPC135062
0.877	High Similarity	NPC216297
0.877	High Similarity	NPC7151
0.877	High Similarity	NPC473662
0.8769	High Similarity	NPC50924
0.876	High Similarity	NPC70622
0.875	High Similarity	NPC477453
0.874	High Similarity	NPC179898
0.874	High Similarity	NPC48248
0.873	High Similarity	NPC15837
0.8722	High Similarity	NPC477408
0.8722	High Similarity	NPC103337
0.8722	High Similarity	NPC114620
0.872	High Similarity	NPC68756
0.872	High Similarity	NPC152525
0.8702	High Similarity	NPC22222
0.8702	High Similarity	NPC281513
0.8692	High Similarity	NPC225051
0.8692	High Similarity	NPC53896
0.8692	High Similarity	NPC52407
0.8678	High Similarity	NPC269414
0.8651	High Similarity	NPC123506
0.8636	High Similarity	NPC474311
0.8636	High Similarity	NPC86524
0.8636	High Similarity	NPC155211
0.8626	High Similarity	NPC288089
0.8615	High Similarity	NPC58685
0.8615	High Similarity	NPC477406
0.8615	High Similarity	NPC88864
0.8607	High Similarity	NPC41567
0.8605	High Similarity	NPC31799
0.8605	High Similarity	NPC475741
0.8583	High Similarity	NPC160499
0.8571	High Similarity	NPC173978
0.8571	High Similarity	NPC471452
0.8561	High Similarity	NPC80035
0.8561	High Similarity	NPC161632
0.8561	High Similarity	NPC283088
0.856	High Similarity	NPC282577
0.856	High Similarity	NPC91478
0.855	High Similarity	NPC115458
0.855	High Similarity	NPC193169
0.855	High Similarity	NPC294226
0.8548	High Similarity	NPC472046
0.8547	High Similarity	NPC224584
0.8538	High Similarity	NPC17083
0.8525	High Similarity	NPC125252
0.8516	High Similarity	NPC45537
0.8516	High Similarity	NPC324209
0.8504	High Similarity	NPC287473
0.8496	Intermediate Similarity	NPC315275
0.8496	Intermediate Similarity	NPC272268
0.8496	Intermediate Similarity	NPC193358
0.8496	Intermediate Similarity	NPC474813
0.8492	Intermediate Similarity	NPC477153
0.8492	Intermediate Similarity	NPC182646
0.8492	Intermediate Similarity	NPC273683
0.8485	Intermediate Similarity	NPC44437
0.848	Intermediate Similarity	NPC120545
0.8473	Intermediate Similarity	NPC17843
0.8462	Intermediate Similarity	NPC27659
0.8462	Intermediate Similarity	NPC34715
0.8462	Intermediate Similarity	NPC31539
0.845	Intermediate Similarity	NPC767
0.845	Intermediate Similarity	NPC247250
0.8444	Intermediate Similarity	NPC111422
0.8444	Intermediate Similarity	NPC306835
0.8444	Intermediate Similarity	NPC299405
0.8444	Intermediate Similarity	NPC216312
0.8444	Intermediate Similarity	NPC471602
0.8444	Intermediate Similarity	NPC476477
0.8444	Intermediate Similarity	NPC29771
0.8444	Intermediate Similarity	NPC256463
0.8438	Intermediate Similarity	NPC295202
0.8438	Intermediate Similarity	NPC227741
0.8438	Intermediate Similarity	NPC136342
0.8438	Intermediate Similarity	NPC49647
0.8433	Intermediate Similarity	NPC53414
0.8433	Intermediate Similarity	NPC238108
0.8433	Intermediate Similarity	NPC305060
0.8433	Intermediate Similarity	NPC53206
0.8433	Intermediate Similarity	NPC245923
0.8421	Intermediate Similarity	NPC258502
0.8417	Intermediate Similarity	NPC231717
0.8413	Intermediate Similarity	NPC164947
0.8406	Intermediate Similarity	NPC477409
0.84	Intermediate Similarity	NPC190971
0.8385	Intermediate Similarity	NPC25736
0.8385	Intermediate Similarity	NPC171460
0.8382	Intermediate Similarity	NPC241349
0.8382	Intermediate Similarity	NPC37992
0.8382	Intermediate Similarity	NPC327916
0.8382	Intermediate Similarity	NPC147542
0.8382	Intermediate Similarity	NPC32749
0.8382	Intermediate Similarity	NPC220496
0.8382	Intermediate Similarity	NPC42262
0.837	Intermediate Similarity	NPC4214
0.837	Intermediate Similarity	NPC416
0.837	Intermediate Similarity	NPC13715
0.837	Intermediate Similarity	NPC61590
0.837	Intermediate Similarity	NPC61398
0.8359	Intermediate Similarity	NPC131799
0.8358	Intermediate Similarity	NPC254847
0.8358	Intermediate Similarity	NPC141934
0.8358	Intermediate Similarity	NPC232996
0.8346	Intermediate Similarity	NPC166480
0.8346	Intermediate Similarity	NPC275145
0.8346	Intermediate Similarity	NPC282780
0.8333	Intermediate Similarity	NPC198336
0.8333	Intermediate Similarity	NPC478190
0.8321	Intermediate Similarity	NPC257003
0.8321	Intermediate Similarity	NPC471444
0.8321	Intermediate Similarity	NPC84273
0.8309	Intermediate Similarity	NPC242994
0.8309	Intermediate Similarity	NPC143438
0.8309	Intermediate Similarity	NPC295339
0.8309	Intermediate Similarity	NPC138099
0.8309	Intermediate Similarity	NPC26924
0.8308	Intermediate Similarity	NPC96024
0.8308	Intermediate Similarity	NPC95537
0.8296	Intermediate Similarity	NPC471905
0.8296	Intermediate Similarity	NPC301341
0.8296	Intermediate Similarity	NPC147418
0.8296	Intermediate Similarity	NPC284184
0.8295	Intermediate Similarity	NPC254492
0.8281	Intermediate Similarity	NPC199273
0.8281	Intermediate Similarity	NPC236189
0.8273	Intermediate Similarity	NPC29932
0.8273	Intermediate Similarity	NPC471906
0.8273	Intermediate Similarity	NPC79627
0.8271	Intermediate Similarity	NPC314048
0.8268	Intermediate Similarity	NPC217756
0.8268	Intermediate Similarity	NPC283514
0.8268	Intermediate Similarity	NPC46634
0.8261	Intermediate Similarity	NPC291078
0.8261	Intermediate Similarity	NPC474300
0.8258	Intermediate Similarity	NPC85342
0.8258	Intermediate Similarity	NPC93015
0.8254	Intermediate Similarity	NPC35856
0.8254	Intermediate Similarity	NPC165197
0.8254	Intermediate Similarity	NPC292665
0.8254	Intermediate Similarity	NPC115188
0.8254	Intermediate Similarity	NPC159760
0.8254	Intermediate Similarity	NPC26433
0.8254	Intermediate Similarity	NPC244994
0.8254	Intermediate Similarity	NPC222876
0.8254	Intermediate Similarity	NPC178395
0.8254	Intermediate Similarity	NPC301987
0.8254	Intermediate Similarity	NPC272454
0.8254	Intermediate Similarity	NPC179092
0.8248	Intermediate Similarity	NPC156872
0.8248	Intermediate Similarity	NPC183345
0.8248	Intermediate Similarity	NPC169452
0.8248	Intermediate Similarity	NPC315578
0.8248	Intermediate Similarity	NPC181560
0.824	Intermediate Similarity	NPC233165
0.824	Intermediate Similarity	NPC184579
0.8231	Intermediate Similarity	NPC473787

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 NPC310540 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	305
0.1-0.2	976
0.2-0.3	1420
0.3-0.4	2751
0.4-0.5	2107
0.5-0.6	1115
0.6-0.7	411
0.7-0.8	59
0.8-0.85	4
0.85-0.9	1
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9231	High Similarity	NPD405	Clinical (unspecified phase)
0.8952	High Similarity	NPD1470	Approved
0.8629	High Similarity	NPD1201	Approved
0.8358	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.8222	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.8071	Intermediate Similarity	NPD3300	Phase 2
0.7842	Intermediate Similarity	NPD2346	Discontinued
0.7794	Intermediate Similarity	NPD943	Approved
0.7787	Intermediate Similarity	NPD9266	Approved
0.7787	Intermediate Similarity	NPD74	Approved
0.774	Intermediate Similarity	NPD3226	Approved
0.7717	Intermediate Similarity	NPD9493	Approved
0.7705	Intermediate Similarity	NPD9267	Approved
0.7705	Intermediate Similarity	NPD9264	Approved
0.7705	Intermediate Similarity	NPD9263	Approved
0.7669	Intermediate Similarity	NPD1164	Approved
0.7643	Intermediate Similarity	NPD5405	Approved
0.7643	Intermediate Similarity	NPD5404	Approved
0.7643	Intermediate Similarity	NPD5406	Approved
0.7643	Intermediate Similarity	NPD5408	Approved
0.7639	Intermediate Similarity	NPD7390	Discontinued
0.7615	Intermediate Similarity	NPD2932	Approved
0.7589	Intermediate Similarity	NPD1471	Phase 3
0.7571	Intermediate Similarity	NPD3299	Clinical (unspecified phase)
0.7538	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7518	Intermediate Similarity	NPD2935	Discontinued
0.7481	Intermediate Similarity	NPD3019	Approved
0.7465	Intermediate Similarity	NPD2344	Approved
0.7422	Intermediate Similarity	NPD9281	Approved
0.7413	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD2313	Discontinued
0.7377	Intermediate Similarity	NPD9261	Approved
0.7357	Intermediate Similarity	NPD447	Suspended
0.7353	Intermediate Similarity	NPD2798	Approved
0.7347	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7324	Intermediate Similarity	NPD2799	Discontinued
0.7313	Intermediate Similarity	NPD9717	Approved
0.7305	Intermediate Similarity	NPD1607	Approved
0.7286	Intermediate Similarity	NPD1240	Approved
0.728	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7279	Intermediate Similarity	NPD1203	Approved
0.7266	Intermediate Similarity	NPD411	Approved
0.726	Intermediate Similarity	NPD2309	Approved
0.725	Intermediate Similarity	NPD288	Approved
0.723	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7213	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.7203	Intermediate Similarity	NPD1510	Phase 2
0.7192	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD1609	Clinical (unspecified phase)
0.7181	Intermediate Similarity	NPD1512	Approved
0.7177	Intermediate Similarity	NPD1237	Approved
0.7167	Intermediate Similarity	NPD844	Approved
0.7143	Intermediate Similarity	NPD3764	Approved
0.7132	Intermediate Similarity	NPD7635	Approved
0.7114	Intermediate Similarity	NPD2532	Approved
0.7114	Intermediate Similarity	NPD2534	Approved
0.7114	Intermediate Similarity	NPD2533	Approved
0.7089	Intermediate Similarity	NPD6232	Discontinued
0.7087	Intermediate Similarity	NPD6831	Clinical (unspecified phase)
0.7068	Intermediate Similarity	NPD9545	Approved
0.7063	Intermediate Similarity	NPD7473	Discontinued
0.7059	Intermediate Similarity	NPD9269	Phase 2
0.7055	Intermediate Similarity	NPD5029	Approved
0.7055	Intermediate Similarity	NPD5031	Approved
0.7055	Intermediate Similarity	NPD5027	Approved
0.7047	Intermediate Similarity	NPD1511	Approved
0.704	Intermediate Similarity	NPD164	Approved
0.7037	Intermediate Similarity	NPD3026	Approved
0.7037	Intermediate Similarity	NPD3023	Approved
0.7023	Intermediate Similarity	NPD5951	Approved
0.7015	Intermediate Similarity	NPD9268	Approved
0.7015	Intermediate Similarity	NPD3024	Approved
0.7015	Intermediate Similarity	NPD3025	Approved
0.7012	Intermediate Similarity	NPD4955	Approved
0.7012	Intermediate Similarity	NPD4954	Approved
0.7012	Intermediate Similarity	NPD5034	Approved
0.7012	Intermediate Similarity	NPD5026	Approved
0.7012	Intermediate Similarity	NPD36	Approved
0.7012	Intermediate Similarity	NPD5028	Approved
0.7008	Intermediate Similarity	NPD2342	Discontinued
0.7007	Intermediate Similarity	NPD2800	Approved
0.7007	Intermediate Similarity	NPD1755	Approved
0.6987	Remote Similarity	NPD3882	Suspended
0.6985	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6972	Remote Similarity	NPD520	Approved
0.6968	Remote Similarity	NPD7819	Suspended
0.6959	Remote Similarity	NPD3750	Approved
0.6957	Remote Similarity	NPD1283	Approved
0.6957	Remote Similarity	NPD1876	Approved
0.6951	Remote Similarity	NPD5030	Phase 2
0.6946	Remote Similarity	NPD8150	Discontinued
0.6939	Remote Similarity	NPD1549	Phase 2
0.6934	Remote Similarity	NPD4878	Approved
0.6929	Remote Similarity	NPD9494	Approved
0.6923	Remote Similarity	NPD650	Approved
0.6918	Remote Similarity	NPD1551	Phase 2
0.6899	Remote Similarity	NPD4750	Phase 3
0.6889	Remote Similarity	NPD1651	Approved
0.6875	Remote Similarity	NPD230	Phase 1
0.6875	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6871	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6871	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6871	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.686	Remote Similarity	NPD845	Approved
0.6859	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6859	Remote Similarity	NPD2801	Approved
0.6846	Remote Similarity	NPD7003	Approved
0.6846	Remote Similarity	NPD8166	Discontinued
0.6846	Remote Similarity	NPD4141	Clinical (unspecified phase)
0.6845	Remote Similarity	NPD5038	Approved
0.6845	Remote Similarity	NPD5037	Approved
0.6838	Remote Similarity	NPD4626	Approved
0.6838	Remote Similarity	NPD7163	Clinical (unspecified phase)
0.6825	Remote Similarity	NPD1929	Approved
0.6825	Remote Similarity	NPD1930	Approved
0.6825	Remote Similarity	NPD1931	Clinical (unspecified phase)
0.6822	Remote Similarity	NPD2182	Approved
0.6818	Remote Similarity	NPD1241	Discontinued
0.6813	Remote Similarity	NPD6959	Discontinued
0.6812	Remote Similarity	NPD3972	Approved
0.6795	Remote Similarity	NPD1934	Approved
0.6788	Remote Similarity	NPD4879	Approved
0.6786	Remote Similarity	NPD5036	Approved
0.6784	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6776	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD4380	Phase 2
0.6767	Remote Similarity	NPD497	Approved
0.6765	Remote Similarity	NPD6836	Approved
0.6761	Remote Similarity	NPD6832	Phase 2
0.675	Remote Similarity	NPD9258	Approved
0.675	Remote Similarity	NPD9256	Approved
0.6746	Remote Similarity	NPD1932	Approved
0.6739	Remote Similarity	NPD1281	Approved
0.6738	Remote Similarity	NPD1019	Discontinued
0.6736	Remote Similarity	NPD6663	Approved
0.6735	Remote Similarity	NPD4308	Phase 3
0.6733	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.673	Remote Similarity	NPD7075	Discontinued
0.673	Remote Similarity	NPD3749	Approved
0.672	Remote Similarity	NPD3020	Approved
0.6715	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6711	Remote Similarity	NPD6799	Approved
0.671	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6709	Remote Similarity	NPD2296	Approved
0.6709	Remote Similarity	NPD5402	Approved
0.6694	Remote Similarity	NPD7609	Phase 3
0.6692	Remote Similarity	NPD498	Approved
0.6692	Remote Similarity	NPD495	Approved
0.6692	Remote Similarity	NPD496	Approved
0.6691	Remote Similarity	NPD1608	Approved
0.669	Remote Similarity	NPD5736	Approved
0.6688	Remote Similarity	NPD6844	Discontinued
0.6667	Remote Similarity	NPD2933	Approved
0.6667	Remote Similarity	NPD6599	Discontinued
0.6667	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD3268	Approved
0.6667	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD2934	Approved
0.6667	Remote Similarity	NPD1432	Clinical (unspecified phase)
0.6646	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6642	Remote Similarity	NPD690	Clinical (unspecified phase)
0.6641	Remote Similarity	NPD3022	Approved
0.6641	Remote Similarity	NPD3021	Approved
0.6639	Remote Similarity	NPD7631	Approved
0.6622	Remote Similarity	NPD3748	Approved
0.6613	Remote Similarity	NPD1809	Phase 2
0.6613	Remote Similarity	NPD2859	Approved
0.6613	Remote Similarity	NPD2860	Approved
0.6609	Remote Similarity	NPD6535	Approved
0.6609	Remote Similarity	NPD6534	Approved
0.6607	Remote Similarity	NPD5032	Approved
0.6606	Remote Similarity	NPD3751	Discontinued
0.6604	Remote Similarity	NPD3817	Phase 2
0.6604	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6603	Remote Similarity	NPD7458	Discontinued
0.6599	Remote Similarity	NPD6651	Approved
0.659	Remote Similarity	NPD5968	Phase 3
0.6587	Remote Similarity	NPD2066	Phase 3
0.6585	Remote Similarity	NPD6166	Phase 2
0.6585	Remote Similarity	NPD1202	Approved
0.6585	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6585	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6577	Remote Similarity	NPD6100	Approved
0.6577	Remote Similarity	NPD6099	Approved
0.6577	Remote Similarity	NPD2796	Approved
0.6575	Remote Similarity	NPD4060	Phase 1
0.6569	Remote Similarity	NPD3091	Approved
0.6569	Remote Similarity	NPD1759	Phase 1
0.6568	Remote Similarity	NPD8312	Approved
0.6568	Remote Similarity	NPD5035	Approved
0.6568	Remote Similarity	NPD8313	Approved
0.6565	Remote Similarity	NPD2329	Discontinued
0.6564	Remote Similarity	NPD5711	Approved
0.6564	Remote Similarity	NPD5710	Approved
0.6549	Remote Similarity	NPD2797	Approved
0.6545	Remote Similarity	NPD5033	Approved
0.6536	Remote Similarity	NPD7236	Approved
0.6534	Remote Similarity	NPD7282	Approved
0.6525	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6525	Remote Similarity	NPD3600	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