NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	218.06
Volume:	218.338
LogP:	1.459
LogD:	1.174
LogS:	-3.804
# Rotatable Bonds:	1
TPSA:	60.44
# H-Bond Aceptor:	4
# H-Bond Donor:	0
# Rings:	2
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.526
Synthetic Accessibility Score:	2.838
Fsp3:	0.25
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:	-4.595
MDCK Permeability:	3.52616589225363e-05
Pgp-inhibitor:	0.041
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.005
30% Bioavailability (F30%):	0.86

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.466
Plasma Protein Binding (PPB):	92.38831329345703%
Volume Distribution (VD):	0.589
Pgp-substrate:	1.585941195487976%

ADMET: Metabolism

CYP1A2-inhibitor:	0.958
CYP1A2-substrate:	0.812
CYP2C19-inhibitor:	0.306
CYP2C19-substrate:	0.448
CYP2C9-inhibitor:	0.237
CYP2C9-substrate:	0.476
CYP2D6-inhibitor:	0.192
CYP2D6-substrate:	0.42
CYP3A4-inhibitor:	0.272
CYP3A4-substrate:	0.249

ADMET: Excretion

Clearance (CL):	4.402
Half-life (T1/2):	0.275

ADMET: Toxicity

hERG Blockers:	0.012
Human Hepatotoxicity (H-HT):	0.094
Drug-inuced Liver Injury (DILI):	0.916
AMES Toxicity:	0.684
Rat Oral Acute Toxicity:	0.14
Maximum Recommended Daily Dose:	0.031
Skin Sensitization:	0.278
Carcinogencity:	0.602
Eye Corrosion:	0.011
Eye Irritation:	0.245
Respiratory Toxicity:	0.358

Download Data

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

Natural Product: NPC205360

Natural Product ID:	NPC205360
*Common Name:**	OMXXTPLHUKBYKI-UHFFFAOYSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	OMXXTPLHUKBYKI-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C12H10O4/c1-6-10(13)7-4-3-5-8(16-2)9(7)12(15)11(6)14/h3-5,14H,1-2H3
SMILES:	CC1=C(C(=O)c2c(cccc2OC)C1=O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2071230
PubChem CID:	n.a.
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
NPO32707	burman diospyros burmanica	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[22858297]

☑ 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

Activity Type	# Activity
Cell Line	1
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	>	100000.0	nM	PMID[551407]
NPT841	Organism	Leishmania major	Leishmania major	IC50	>	100000.0	nM	PMID[551407]

☑ 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 NPC205360 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	329
0.1-0.2	1596
0.2-0.3	4208
0.3-0.4	10142
0.4-0.5	8086
0.5-0.6	4558
0.6-0.7	7984
0.7-0.8	5469
0.8-0.85	267
0.85-0.9	43
0.9-0.95	14
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9394	High Similarity	NPC477408
0.9365	High Similarity	NPC45537
0.9355	High Similarity	NPC182646
0.9291	High Similarity	NPC237225
0.9237	High Similarity	NPC22222
0.9237	High Similarity	NPC281513
0.9167	High Similarity	NPC232996
0.9134	High Similarity	NPC51037
0.9127	High Similarity	NPC310540
0.9098	High Similarity	NPC301341
0.9098	High Similarity	NPC284184
0.9	High Similarity	NPC198305
0.8915	High Similarity	NPC470841
0.8913	High Similarity	NPC477409
0.8881	High Similarity	NPC141934
0.8846	High Similarity	NPC165257
0.8837	High Similarity	NPC231774
0.8832	High Similarity	NPC84273
0.8797	High Similarity	NPC171968
0.8788	High Similarity	NPC477412
0.873	High Similarity	NPC206778
0.873	High Similarity	NPC285829
0.8722	High Similarity	NPC309430
0.8722	High Similarity	NPC477406
0.8696	High Similarity	NPC124365
0.8692	High Similarity	NPC1991
0.8686	High Similarity	NPC1268
0.8667	High Similarity	NPC22644
0.8643	High Similarity	NPC475201
0.8643	High Similarity	NPC274085
0.8643	High Similarity	NPC89664
0.8636	High Similarity	NPC57552
0.8633	High Similarity	NPC69755
0.8613	High Similarity	NPC173980
0.8593	High Similarity	NPC1249
0.8592	High Similarity	NPC252208
0.8582	High Similarity	NPC28632
0.8571	High Similarity	NPC53016
0.8571	High Similarity	NPC171023
0.8551	High Similarity	NPC470407
0.855	High Similarity	NPC306765
0.8527	High Similarity	NPC307174
0.8521	High Similarity	NPC300540
0.8519	High Similarity	NPC254603
0.8496	Intermediate Similarity	NPC278928
0.8478	Intermediate Similarity	NPC475104
0.8467	Intermediate Similarity	NPC471670
0.8462	Intermediate Similarity	NPC135062
0.8451	Intermediate Similarity	NPC478019
0.8451	Intermediate Similarity	NPC73416
0.8451	Intermediate Similarity	NPC160777
0.8444	Intermediate Similarity	NPC312560
0.8435	Intermediate Similarity	NPC3898
0.8417	Intermediate Similarity	NPC223336
0.8413	Intermediate Similarity	NPC108288
0.8409	Intermediate Similarity	NPC3224
0.8409	Intermediate Similarity	NPC177925
0.8406	Intermediate Similarity	NPC477534
0.8397	Intermediate Similarity	NPC56332
0.8397	Intermediate Similarity	NPC4012
0.8394	Intermediate Similarity	NPC217914
0.8382	Intermediate Similarity	NPC477536
0.838	Intermediate Similarity	NPC19896
0.837	Intermediate Similarity	NPC324488
0.8359	Intermediate Similarity	NPC232178
0.8357	Intermediate Similarity	NPC109007
0.8357	Intermediate Similarity	NPC477537
0.8346	Intermediate Similarity	NPC71525
0.8345	Intermediate Similarity	NPC226578
0.8333	Intermediate Similarity	NPC478018
0.8333	Intermediate Similarity	NPC224657
0.8322	Intermediate Similarity	NPC67197
0.8322	Intermediate Similarity	NPC474630
0.8321	Intermediate Similarity	NPC375356
0.8321	Intermediate Similarity	NPC93730
0.8309	Intermediate Similarity	NPC88864
0.8309	Intermediate Similarity	NPC246693
0.8309	Intermediate Similarity	NPC242358
0.8309	Intermediate Similarity	NPC110609
0.8298	Intermediate Similarity	NPC283292
0.8296	Intermediate Similarity	NPC117609
0.8296	Intermediate Similarity	NPC475741
0.8296	Intermediate Similarity	NPC136588
0.8296	Intermediate Similarity	NPC199253
0.8286	Intermediate Similarity	NPC306835
0.8286	Intermediate Similarity	NPC476477
0.8286	Intermediate Similarity	NPC299405
0.8286	Intermediate Similarity	NPC114620
0.8286	Intermediate Similarity	NPC103337
0.8286	Intermediate Similarity	NPC29771
0.8286	Intermediate Similarity	NPC111422
0.8286	Intermediate Similarity	NPC256463
0.8286	Intermediate Similarity	NPC216312
0.8286	Intermediate Similarity	NPC471602
0.8271	Intermediate Similarity	NPC96915
0.8271	Intermediate Similarity	NPC474737
0.8258	Intermediate Similarity	NPC74507
0.8258	Intermediate Similarity	NPC234890
0.8252	Intermediate Similarity	NPC469385
0.8248	Intermediate Similarity	NPC59459
0.8248	Intermediate Similarity	NPC193169
0.8244	Intermediate Similarity	NPC217756
0.8244	Intermediate Similarity	NPC300274
0.8244	Intermediate Similarity	NPC46634
0.8239	Intermediate Similarity	NPC11314
0.8239	Intermediate Similarity	NPC329493
0.8239	Intermediate Similarity	NPC49108
0.8235	Intermediate Similarity	NPC141549
0.8231	Intermediate Similarity	NPC144283
0.8227	Intermediate Similarity	NPC42262
0.8227	Intermediate Similarity	NPC37992
0.8227	Intermediate Similarity	NPC147542
0.8227	Intermediate Similarity	NPC241349
0.8227	Intermediate Similarity	NPC156872
0.8227	Intermediate Similarity	NPC32749
0.8227	Intermediate Similarity	NPC220496
0.8227	Intermediate Similarity	NPC327916
0.8227	Intermediate Similarity	NPC477535
0.8222	Intermediate Similarity	NPC34414
0.8222	Intermediate Similarity	NPC146647
0.8219	Intermediate Similarity	NPC80370
0.8214	Intermediate Similarity	NPC61590
0.8214	Intermediate Similarity	NPC265181
0.8209	Intermediate Similarity	NPC298884
0.8207	Intermediate Similarity	NPC126767
0.8207	Intermediate Similarity	NPC312929
0.8207	Intermediate Similarity	NPC118027
0.8207	Intermediate Similarity	NPC289042
0.8207	Intermediate Similarity	NPC245584
0.8207	Intermediate Similarity	NPC190648
0.8207	Intermediate Similarity	NPC56433
0.8203	Intermediate Similarity	NPC240664
0.8201	Intermediate Similarity	NPC475549
0.82	Intermediate Similarity	NPC476404
0.82	Intermediate Similarity	NPC294300
0.82	Intermediate Similarity	NPC317900
0.8195	Intermediate Similarity	NPC103540
0.8188	Intermediate Similarity	NPC274876
0.8182	Intermediate Similarity	NPC215451
0.8182	Intermediate Similarity	NPC476473
0.8182	Intermediate Similarity	NPC277369
0.8175	Intermediate Similarity	NPC183103
0.8175	Intermediate Similarity	NPC279916
0.8175	Intermediate Similarity	NPC118253
0.8175	Intermediate Similarity	NPC70622
0.8175	Intermediate Similarity	NPC474340
0.8175	Intermediate Similarity	NPC470160
0.8169	Intermediate Similarity	NPC471444
0.8169	Intermediate Similarity	NPC257003
0.8163	Intermediate Similarity	NPC255641
0.8163	Intermediate Similarity	NPC147735
0.8163	Intermediate Similarity	NPC290954
0.8163	Intermediate Similarity	NPC294646
0.8162	Intermediate Similarity	NPC470725
0.8162	Intermediate Similarity	NPC55949
0.8162	Intermediate Similarity	NPC7569
0.8162	Intermediate Similarity	NPC27659
0.8162	Intermediate Similarity	NPC278787
0.8156	Intermediate Similarity	NPC295339
0.8154	Intermediate Similarity	NPC216297
0.8154	Intermediate Similarity	NPC7151
0.8154	Intermediate Similarity	NPC470092
0.8154	Intermediate Similarity	NPC473662
0.8151	Intermediate Similarity	NPC2569
0.8151	Intermediate Similarity	NPC172329
0.8148	Intermediate Similarity	NPC282923
0.8143	Intermediate Similarity	NPC470722
0.8143	Intermediate Similarity	NPC186647
0.8143	Intermediate Similarity	NPC470721
0.8143	Intermediate Similarity	NPC156888
0.8143	Intermediate Similarity	NPC6100
0.8143	Intermediate Similarity	NPC471542
0.8134	Intermediate Similarity	NPC474264
0.8129	Intermediate Similarity	NPC298900
0.8121	Intermediate Similarity	NPC155686
0.8121	Intermediate Similarity	NPC127172
0.812	Intermediate Similarity	NPC152525
0.812	Intermediate Similarity	NPC470162
0.812	Intermediate Similarity	NPC142956
0.812	Intermediate Similarity	NPC91475
0.812	Intermediate Similarity	NPC68756
0.812	Intermediate Similarity	NPC265910
0.812	Intermediate Similarity	NPC470163
0.8116	Intermediate Similarity	NPC52407
0.8116	Intermediate Similarity	NPC470406
0.8116	Intermediate Similarity	NPC263817
0.8112	Intermediate Similarity	NPC182255
0.8112	Intermediate Similarity	NPC94076
0.8112	Intermediate Similarity	NPC474300
0.8108	Intermediate Similarity	NPC132990
0.8108	Intermediate Similarity	NPC118427
0.8108	Intermediate Similarity	NPC46882
0.8108	Intermediate Similarity	NPC230848
0.8108	Intermediate Similarity	NPC473201
0.8108	Intermediate Similarity	NPC302783
0.8106	Intermediate Similarity	NPC164947
0.8102	Intermediate Similarity	NPC244699
0.8102	Intermediate Similarity	NPC239134
0.8102	Intermediate Similarity	NPC279596
0.8102	Intermediate Similarity	NPC205992

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 NPC205360 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	303
0.1-0.2	993
0.2-0.3	1428
0.3-0.4	2544
0.4-0.5	2015
0.5-0.6	1214
0.6-0.7	519
0.7-0.8	126
0.8-0.85	7
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8478	Intermediate Similarity	NPD2346	Discontinued
0.8413	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.8219	Intermediate Similarity	NPD3226	Approved
0.8214	Intermediate Similarity	NPD1471	Phase 3
0.8195	Intermediate Similarity	NPD1470	Approved
0.8029	Intermediate Similarity	NPD2313	Discontinued
0.8014	Intermediate Similarity	NPD2935	Discontinued
0.8	Intermediate Similarity	NPD2798	Approved
0.7943	Intermediate Similarity	NPD2799	Discontinued
0.7902	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7895	Intermediate Similarity	NPD1201	Approved
0.7857	Intermediate Similarity	NPD447	Suspended
0.7836	Intermediate Similarity	NPD9717	Approved
0.7832	Intermediate Similarity	NPD2344	Approved
0.7801	Intermediate Similarity	NPD1607	Approved
0.7786	Intermediate Similarity	NPD1240	Approved
0.777	Intermediate Similarity	NPD411	Approved
0.7761	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7721	Intermediate Similarity	NPD1283	Approved
0.7721	Intermediate Similarity	NPD1876	Approved
0.771	Intermediate Similarity	NPD9493	Approved
0.7703	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD1510	Phase 2
0.7692	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7671	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7669	Intermediate Similarity	NPD1651	Approved
0.7664	Intermediate Similarity	NPD1203	Approved
0.7647	Intermediate Similarity	NPD7819	Suspended
0.7619	Intermediate Similarity	NPD2309	Approved
0.7615	Intermediate Similarity	NPD1241	Discontinued
0.7606	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7586	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7584	Intermediate Similarity	NPD2532	Approved
0.7584	Intermediate Similarity	NPD2533	Approved
0.7584	Intermediate Similarity	NPD2534	Approved
0.7574	Intermediate Similarity	NPD3972	Approved
0.7569	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7533	Intermediate Similarity	NPD1512	Approved
0.7532	Intermediate Similarity	NPD6232	Discontinued
0.75	Intermediate Similarity	NPD1281	Approved
0.75	Intermediate Similarity	NPD7473	Discontinued
0.75	Intermediate Similarity	NPD6832	Phase 2
0.7482	Intermediate Similarity	NPD1019	Discontinued
0.7481	Intermediate Similarity	NPD4626	Approved
0.7462	Intermediate Similarity	NPD1609	Clinical (unspecified phase)
0.745	Intermediate Similarity	NPD3300	Phase 2
0.7436	Intermediate Similarity	NPD3882	Suspended
0.7432	Intermediate Similarity	NPD7003	Approved
0.7429	Intermediate Similarity	NPD9494	Approved
0.7415	Intermediate Similarity	NPD1549	Phase 2
0.74	Intermediate Similarity	NPD1511	Approved
0.74	Intermediate Similarity	NPD6799	Approved
0.7397	Intermediate Similarity	NPD1551	Phase 2
0.7365	Intermediate Similarity	NPD2800	Approved
0.7355	Intermediate Similarity	NPD6844	Discontinued
0.7347	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7347	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7338	Intermediate Similarity	NPD6599	Discontinued
0.7323	Intermediate Similarity	NPD164	Approved
0.7319	Intermediate Similarity	NPD1608	Approved
0.7315	Intermediate Similarity	NPD3750	Approved
0.7308	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD2801	Approved
0.7308	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7279	Intermediate Similarity	NPD2796	Approved
0.7279	Intermediate Similarity	NPD5691	Approved
0.7273	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7261	Intermediate Similarity	NPD3817	Phase 2
0.7261	Intermediate Similarity	NPD5402	Approved
0.725	Intermediate Similarity	NPD6959	Discontinued
0.7248	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7244	Intermediate Similarity	NPD1934	Approved
0.7226	Intermediate Similarity	NPD1778	Approved
0.7226	Intermediate Similarity	NPD4380	Phase 2
0.7211	Intermediate Similarity	NPD4308	Phase 3
0.7211	Intermediate Similarity	NPD3748	Approved
0.7193	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD6273	Approved
0.7172	Intermediate Similarity	NPD2979	Phase 3
0.7172	Intermediate Similarity	NPD943	Approved
0.717	Intermediate Similarity	NPD7075	Discontinued
0.7161	Intermediate Similarity	NPD2651	Approved
0.7161	Intermediate Similarity	NPD2649	Approved
0.7161	Intermediate Similarity	NPD7458	Discontinued
0.7154	Intermediate Similarity	NPD9267	Approved
0.7154	Intermediate Similarity	NPD9264	Approved
0.7154	Intermediate Similarity	NPD9263	Approved
0.7153	Intermediate Similarity	NPD3268	Approved
0.7143	Intermediate Similarity	NPD920	Approved
0.7143	Intermediate Similarity	NPD1247	Approved
0.7134	Intermediate Similarity	NPD3751	Discontinued
0.7124	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7124	Intermediate Similarity	NPD5401	Approved
0.7123	Intermediate Similarity	NPD1933	Approved
0.7122	Intermediate Similarity	NPD1611	Approved
0.7101	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD17	Approved
0.7099	Intermediate Similarity	NPD74	Approved
0.7099	Intermediate Similarity	NPD9266	Approved
0.7099	Intermediate Similarity	NPD2182	Approved
0.7086	Intermediate Similarity	NPD4628	Phase 3
0.7086	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD5494	Approved
0.708	Intermediate Similarity	NPD9545	Approved
0.7076	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7075	Intermediate Similarity	NPD6651	Approved
0.707	Intermediate Similarity	NPD7411	Suspended
0.7063	Intermediate Similarity	NPD3749	Approved
0.7059	Intermediate Similarity	NPD7390	Discontinued
0.7055	Intermediate Similarity	NPD4060	Phase 1
0.7055	Intermediate Similarity	NPD3926	Phase 2
0.7055	Intermediate Similarity	NPD4307	Phase 2
0.705	Intermediate Similarity	NPD3496	Discontinued
0.7047	Intermediate Similarity	NPD5406	Approved
0.7047	Intermediate Similarity	NPD5404	Approved
0.7047	Intermediate Similarity	NPD5405	Approved
0.7047	Intermediate Similarity	NPD5408	Approved
0.7044	Intermediate Similarity	NPD2296	Approved
0.7044	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7042	Intermediate Similarity	NPD1164	Approved
0.7042	Intermediate Similarity	NPD3267	Approved
0.7042	Intermediate Similarity	NPD3266	Approved
0.7042	Intermediate Similarity	NPD2797	Approved
0.7034	Intermediate Similarity	NPD3764	Approved
0.7034	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7032	Intermediate Similarity	NPD5403	Approved
0.7025	Intermediate Similarity	NPD6801	Discontinued
0.7021	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.702	Intermediate Similarity	NPD1243	Approved
0.7019	Intermediate Similarity	NPD919	Approved
0.7013	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7012	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7012	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7012	Intermediate Similarity	NPD6166	Phase 2
0.7007	Intermediate Similarity	NPD6355	Discontinued
0.7007	Intermediate Similarity	NPD5536	Phase 2
0.6994	Remote Similarity	NPD5710	Approved
0.6994	Remote Similarity	NPD5711	Approved
0.6985	Remote Similarity	NPD709	Approved
0.6982	Remote Similarity	NPD8312	Approved
0.6982	Remote Similarity	NPD8313	Approved
0.698	Remote Similarity	NPD3299	Clinical (unspecified phase)
0.6978	Remote Similarity	NPD2932	Approved
0.6977	Remote Similarity	NPD9261	Approved
0.6959	Remote Similarity	NPD8150	Discontinued
0.6959	Remote Similarity	NPD8434	Phase 2
0.6933	Remote Similarity	NPD4476	Approved
0.6933	Remote Similarity	NPD6099	Approved
0.6933	Remote Similarity	NPD4477	Approved
0.6933	Remote Similarity	NPD6100	Approved
0.6928	Remote Similarity	NPD2354	Approved
0.6918	Remote Similarity	NPD6798	Discontinued
0.6918	Remote Similarity	NPD6279	Approved
0.6918	Remote Similarity	NPD6280	Approved
0.6912	Remote Similarity	NPD9281	Approved
0.691	Remote Similarity	NPD6780	Approved
0.691	Remote Similarity	NPD6777	Approved
0.691	Remote Similarity	NPD6778	Approved
0.691	Remote Similarity	NPD6781	Approved
0.691	Remote Similarity	NPD6782	Approved
0.691	Remote Similarity	NPD6779	Approved
0.691	Remote Similarity	NPD6776	Approved
0.6906	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.6903	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6903	Remote Similarity	NPD4661	Approved
0.6903	Remote Similarity	NPD4662	Approved
0.6894	Remote Similarity	NPD7768	Phase 2
0.6892	Remote Similarity	NPD230	Phase 1
0.6887	Remote Similarity	NPD5762	Approved
0.6887	Remote Similarity	NPD5763	Approved
0.6886	Remote Similarity	NPD5844	Phase 1
0.6883	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6871	Remote Similarity	NPD8032	Phase 2
0.6861	Remote Similarity	NPD6671	Approved
0.6859	Remote Similarity	NPD5049	Phase 3
0.6857	Remote Similarity	NPD3019	Approved
0.6852	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6832	Remote Similarity	NPD5616	Clinical (unspecified phase)
0.6831	Remote Similarity	NPD1481	Phase 2
0.6826	Remote Similarity	NPD3818	Discontinued
0.6826	Remote Similarity	NPD7177	Discontinued
0.6824	Remote Similarity	NPD3140	Approved
0.6824	Remote Similarity	NPD3142	Approved
0.6821	Remote Similarity	NPD2531	Phase 2
0.6821	Remote Similarity	NPD2438	Suspended
0.6818	Remote Similarity	NPD3295	Clinical (unspecified phase)
0.6807	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6805	Remote Similarity	NPD6797	Phase 2
0.6803	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6797	Remote Similarity	NPD2654	Approved
0.6796	Remote Similarity	NPD7435	Discontinued
0.6796	Remote Similarity	NPD7697	Approved
0.6796	Remote Similarity	NPD7698	Approved
0.6796	Remote Similarity	NPD7696	Phase 3
0.6794	Remote Similarity	NPD1237	Approved
0.6792	Remote Similarity	NPD7028	Phase 2
0.6788	Remote Similarity	NPD690	Clinical (unspecified phase)
0.6788	Remote Similarity	NPD3787	Discontinued
0.6786	Remote Similarity	NPD7804	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