NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	274.08
Volume:	270.459
LogP:	1.884
LogD:	2.008
LogS:	-3.609
# Rotatable Bonds:	1
TPSA:	90.9
# H-Bond Aceptor:	5
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.743
Synthetic Accessibility Score:	3.735
Fsp3:	0.267
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-5.218
MDCK Permeability:	6.406397915270645e-06
Pgp-inhibitor:	0.005
Pgp-substrate:	0.201
Human Intestinal Absorption (HIA):	0.016
20% Bioavailability (F20%):	0.117
30% Bioavailability (F30%):	0.97

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.022
Plasma Protein Binding (PPB):	94.66979217529297%
Volume Distribution (VD):	0.483
Pgp-substrate:	5.952869892120361%

ADMET: Metabolism

CYP1A2-inhibitor:	0.752
CYP1A2-substrate:	0.251
CYP2C19-inhibitor:	0.11
CYP2C19-substrate:	0.065
CYP2C9-inhibitor:	0.412
CYP2C9-substrate:	0.733
CYP2D6-inhibitor:	0.577
CYP2D6-substrate:	0.275
CYP3A4-inhibitor:	0.462
CYP3A4-substrate:	0.146

ADMET: Excretion

Clearance (CL):	7.106
Half-life (T1/2):	0.537

ADMET: Toxicity

hERG Blockers:	0.015
Human Hepatotoxicity (H-HT):	0.28
Drug-inuced Liver Injury (DILI):	0.951
AMES Toxicity:	0.395
Rat Oral Acute Toxicity:	0.777
Maximum Recommended Daily Dose:	0.059
Skin Sensitization:	0.177
Carcinogencity:	0.205
Eye Corrosion:	0.004
Eye Irritation:	0.622
Respiratory Toxicity:	0.381

Download Data

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

Natural Product: NPC42458

Natural Product ID:	NPC42458
*Common Name:**	Leptosphaerin A
IUPAC Name:	(6R,7R)-3-(2,6-dihydroxyphenyl)-7-hydroxy-6-methyl-6,7-dihydro-5H-2-benzofuran-4-one
Synonyms:
Standard InCHIKey:	ONTQFVIAKQPTQW-NXSYQRQQSA-N
Standard InCHI:	InChI=1S/C15H14O5/c1-7-5-11(18)12-8(14(7)19)6-20-15(12)13-9(16)3-2-4-10(13)17/h2-4,6-7,14,16-17,19H,5H2,1H3/t7-,14-/m1/s1
SMILES:	C[C@@H]1CC(=O)c2c(coc2c2c(cccc2O)O)[C@@H]1O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1095143
PubChem CID:	46831106
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0003408] Isobenzofurans

*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
NPO32944	leptosphaeria sp.	Species	Leptosphaeriaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20408555]

☑ 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	3

Activity Type	# Activity
Organism	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT6578	Organism	Microdochium nivale	Microdochium nivale	IC50	>	150000.0	nM	PMID[572961]
NPT826	Organism	Magnaporthe oryzae	Magnaporthe oryzae	IC50	>	150000.0	nM	PMID[572961]
NPT185	Organism	Aspergillus flavus	Aspergillus flavus	IC50	>	150000.0	nM	PMID[572961]

☑ 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 NPC42458 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	371
0.1-0.2	1509
0.2-0.3	3450
0.3-0.4	8664
0.4-0.5	10351
0.5-0.6	4036
0.6-0.7	5889
0.7-0.8	6177
0.8-0.85	1996
0.85-0.9	246
0.9-0.95	6
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC158261
0.9419	High Similarity	NPC136641
0.9221	High Similarity	NPC476349
0.9221	High Similarity	NPC476350
0.9145	High Similarity	NPC67654
0.9091	High Similarity	NPC247677
0.9091	High Similarity	NPC160015
0.9079	High Similarity	NPC156244
0.9032	High Similarity	NPC260902
0.9032	High Similarity	NPC296957
0.8933	High Similarity	NPC98926
0.8854	High Similarity	NPC472877
0.8831	High Similarity	NPC115324
0.879	High Similarity	NPC164110
0.879	High Similarity	NPC246647
0.879	High Similarity	NPC212967
0.879	High Similarity	NPC96342
0.8782	High Similarity	NPC148938
0.8774	High Similarity	NPC207624
0.8774	High Similarity	NPC253872
0.8774	High Similarity	NPC263676
0.8742	High Similarity	NPC24761
0.8734	High Similarity	NPC40583
0.8726	High Similarity	NPC180924
0.8718	High Similarity	NPC1477
0.8718	High Similarity	NPC235333
0.8718	High Similarity	NPC213608
0.8718	High Similarity	NPC122365
0.871	High Similarity	NPC116604
0.871	High Similarity	NPC23668
0.871	High Similarity	NPC170169
0.871	High Similarity	NPC58668
0.871	High Similarity	NPC193976
0.871	High Similarity	NPC106372
0.8701	High Similarity	NPC226644
0.8701	High Similarity	NPC37226
0.8701	High Similarity	NPC39929
0.8701	High Similarity	NPC296030
0.8693	High Similarity	NPC17816
0.8693	High Similarity	NPC71055
0.8684	High Similarity	NPC155144
0.8684	High Similarity	NPC230943
0.8675	High Similarity	NPC53192
0.8671	High Similarity	NPC317900
0.8671	High Similarity	NPC294300
0.8671	High Similarity	NPC476404
0.8671	High Similarity	NPC269495
0.8662	High Similarity	NPC213936
0.8662	High Similarity	NPC297531
0.8662	High Similarity	NPC198490
0.8654	High Similarity	NPC142308
0.8654	High Similarity	NPC5871
0.8645	High Similarity	NPC230713
0.8645	High Similarity	NPC202595
0.8645	High Similarity	NPC167576
0.8645	High Similarity	NPC78335
0.8636	High Similarity	NPC135325
0.8634	High Similarity	NPC100849
0.8627	High Similarity	NPC73320
0.8625	High Similarity	NPC304387
0.8625	High Similarity	NPC269117
0.8618	High Similarity	NPC302181
0.8618	High Similarity	NPC113770
0.8616	High Similarity	NPC226287
0.8609	High Similarity	NPC64568
0.8608	High Similarity	NPC474386
0.8608	High Similarity	NPC221992
0.8599	High Similarity	NPC183874
0.859	High Similarity	NPC207346
0.859	High Similarity	NPC46564
0.8581	High Similarity	NPC317492
0.8581	High Similarity	NPC178202
0.858	High Similarity	NPC474591
0.858	High Similarity	NPC291110
0.8571	High Similarity	NPC130581
0.8571	High Similarity	NPC12148
0.8571	High Similarity	NPC150215
0.8571	High Similarity	NPC193998
0.8571	High Similarity	NPC308200
0.8562	High Similarity	NPC311144
0.8562	High Similarity	NPC303185
0.8562	High Similarity	NPC260296
0.8562	High Similarity	NPC169
0.8562	High Similarity	NPC184649
0.8562	High Similarity	NPC115432
0.8553	High Similarity	NPC473282
0.8553	High Similarity	NPC270044
0.8553	High Similarity	NPC104380
0.8553	High Similarity	NPC268360
0.8553	High Similarity	NPC65504
0.8553	High Similarity	NPC217602
0.8544	High Similarity	NPC474542
0.8544	High Similarity	NPC99199
0.8535	High Similarity	NPC474843
0.8535	High Similarity	NPC41326
0.8535	High Similarity	NPC87708
0.8535	High Similarity	NPC275878
0.8533	High Similarity	NPC112757
0.8528	High Similarity	NPC53640
0.8526	High Similarity	NPC119929
0.8526	High Similarity	NPC476185
0.8526	High Similarity	NPC155882
0.8526	High Similarity	NPC321896
0.8526	High Similarity	NPC472406
0.8519	High Similarity	NPC109180
0.8519	High Similarity	NPC38591
0.8516	High Similarity	NPC5537
0.8516	High Similarity	NPC145467
0.8516	High Similarity	NPC168085
0.8516	High Similarity	NPC39195
0.8509	High Similarity	NPC30655
0.8509	High Similarity	NPC45124
0.8509	High Similarity	NPC74854
0.8509	High Similarity	NPC472346
0.8506	High Similarity	NPC190572
0.8506	High Similarity	NPC210826
0.8506	High Similarity	NPC472629
0.8506	High Similarity	NPC299011
0.8506	High Similarity	NPC300267
0.8506	High Similarity	NPC51641
0.85	High Similarity	NPC244750
0.8497	Intermediate Similarity	NPC225884
0.8491	Intermediate Similarity	NPC164427
0.8485	Intermediate Similarity	NPC131866
0.8481	Intermediate Similarity	NPC72370
0.8481	Intermediate Similarity	NPC472462
0.8481	Intermediate Similarity	NPC290927
0.8477	Intermediate Similarity	NPC316480
0.8477	Intermediate Similarity	NPC137009
0.8477	Intermediate Similarity	NPC37206
0.8476	Intermediate Similarity	NPC320789
0.8476	Intermediate Similarity	NPC476459
0.8471	Intermediate Similarity	NPC474772
0.8471	Intermediate Similarity	NPC471613
0.8471	Intermediate Similarity	NPC474744
0.8471	Intermediate Similarity	NPC232645
0.8471	Intermediate Similarity	NPC472423
0.8471	Intermediate Similarity	NPC39819
0.8471	Intermediate Similarity	NPC72958
0.8462	Intermediate Similarity	NPC471114
0.8462	Intermediate Similarity	NPC226578
0.8452	Intermediate Similarity	NPC252208
0.8452	Intermediate Similarity	NPC7943
0.8452	Intermediate Similarity	NPC113428
0.8452	Intermediate Similarity	NPC198427
0.8452	Intermediate Similarity	NPC123202
0.8452	Intermediate Similarity	NPC22005
0.8452	Intermediate Similarity	NPC61284
0.8447	Intermediate Similarity	NPC220582
0.8447	Intermediate Similarity	NPC304839
0.8447	Intermediate Similarity	NPC470810
0.8447	Intermediate Similarity	NPC49009
0.8442	Intermediate Similarity	NPC124780
0.8442	Intermediate Similarity	NPC297788
0.8442	Intermediate Similarity	NPC470890
0.8442	Intermediate Similarity	NPC87486
0.8442	Intermediate Similarity	NPC97904
0.8442	Intermediate Similarity	NPC271288
0.8442	Intermediate Similarity	NPC224714
0.8438	Intermediate Similarity	NPC477833
0.8438	Intermediate Similarity	NPC44199
0.8434	Intermediate Similarity	NPC472584
0.8434	Intermediate Similarity	NPC307286
0.8431	Intermediate Similarity	NPC202981
0.8431	Intermediate Similarity	NPC158871
0.8431	Intermediate Similarity	NPC73028
0.8431	Intermediate Similarity	NPC226942
0.8431	Intermediate Similarity	NPC96791
0.8431	Intermediate Similarity	NPC470636
0.8428	Intermediate Similarity	NPC175192
0.8424	Intermediate Similarity	NPC53252
0.8421	Intermediate Similarity	NPC182421
0.8418	Intermediate Similarity	NPC40356
0.8418	Intermediate Similarity	NPC473967
0.8418	Intermediate Similarity	NPC154683
0.8418	Intermediate Similarity	NPC130015
0.8418	Intermediate Similarity	NPC271681
0.8418	Intermediate Similarity	NPC281272
0.8418	Intermediate Similarity	NPC38361
0.8408	Intermediate Similarity	NPC470107
0.8408	Intermediate Similarity	NPC471115
0.8408	Intermediate Similarity	NPC148423
0.8408	Intermediate Similarity	NPC135303
0.8408	Intermediate Similarity	NPC472421
0.8408	Intermediate Similarity	NPC147735
0.8408	Intermediate Similarity	NPC29777
0.8408	Intermediate Similarity	NPC255641
0.8408	Intermediate Similarity	NPC37348
0.8408	Intermediate Similarity	NPC290954
0.8408	Intermediate Similarity	NPC13282
0.8405	Intermediate Similarity	NPC159508
0.8405	Intermediate Similarity	NPC155640
0.8397	Intermediate Similarity	NPC191634
0.8397	Intermediate Similarity	NPC27221
0.8397	Intermediate Similarity	NPC7025
0.8397	Intermediate Similarity	NPC228012
0.8397	Intermediate Similarity	NPC256672
0.8395	Intermediate Similarity	NPC14822
0.8395	Intermediate Similarity	NPC18380
0.8395	Intermediate Similarity	NPC96031

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 NPC42458 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	328
0.1-0.2	933
0.2-0.3	1605
0.3-0.4	2617
0.4-0.5	2006
0.5-0.6	1111
0.6-0.7	378
0.7-0.8	149
0.8-0.85	23
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8344	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8344	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8344	Intermediate Similarity	NPD2344	Approved
0.8333	Intermediate Similarity	NPD920	Approved
0.8289	Intermediate Similarity	NPD1549	Phase 2
0.8205	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.8205	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8166	Intermediate Similarity	NPD6559	Discontinued
0.8158	Intermediate Similarity	NPD1551	Phase 2
0.8137	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8129	Intermediate Similarity	NPD2309	Approved
0.8117	Intermediate Similarity	NPD2800	Approved
0.8105	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.8098	Intermediate Similarity	NPD3749	Approved
0.8092	Intermediate Similarity	NPD1510	Phase 2
0.8086	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8079	Intermediate Similarity	NPD1607	Approved
0.8077	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.8075	Intermediate Similarity	NPD1934	Approved
0.8067	Intermediate Similarity	NPD1240	Approved
0.8061	Intermediate Similarity	NPD6959	Discontinued
0.7987	Intermediate Similarity	NPD1471	Phase 3
0.7975	Intermediate Similarity	NPD2534	Approved
0.7975	Intermediate Similarity	NPD2533	Approved
0.7975	Intermediate Similarity	NPD2532	Approved
0.7952	Intermediate Similarity	NPD1247	Approved
0.795	Intermediate Similarity	NPD4380	Phase 2
0.7935	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7927	Intermediate Similarity	NPD3882	Suspended
0.7922	Intermediate Similarity	NPD2796	Approved
0.7914	Intermediate Similarity	NPD7819	Suspended
0.7911	Intermediate Similarity	NPD1511	Approved
0.7892	Intermediate Similarity	NPD5494	Approved
0.7885	Intermediate Similarity	NPD1243	Approved
0.787	Intermediate Similarity	NPD7473	Discontinued
0.7831	Intermediate Similarity	NPD919	Approved
0.7829	Intermediate Similarity	NPD8434	Phase 2
0.7824	Intermediate Similarity	NPD3818	Discontinued
0.7812	Intermediate Similarity	NPD1512	Approved
0.7805	Intermediate Similarity	NPD5760	Phase 2
0.7805	Intermediate Similarity	NPD2801	Approved
0.7805	Intermediate Similarity	NPD5761	Phase 2
0.7798	Intermediate Similarity	NPD6232	Discontinued
0.7778	Intermediate Similarity	NPD3226	Approved
0.7771	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7771	Intermediate Similarity	NPD7075	Discontinued
0.7751	Intermediate Similarity	NPD3926	Phase 2
0.775	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7742	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7722	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7706	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7706	Intermediate Similarity	NPD6166	Phase 2
0.7706	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7697	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7683	Intermediate Similarity	NPD7411	Suspended
0.7643	Intermediate Similarity	NPD2346	Discontinued
0.7636	Intermediate Similarity	NPD6801	Discontinued
0.7622	Intermediate Similarity	NPD6599	Discontinued
0.761	Intermediate Similarity	NPD3750	Approved
0.7605	Intermediate Similarity	NPD7768	Phase 2
0.7602	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.76	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.758	Intermediate Similarity	NPD6099	Approved
0.758	Intermediate Similarity	NPD6100	Approved
0.7578	Intermediate Similarity	NPD6799	Approved
0.7572	Intermediate Similarity	NPD5844	Phase 1
0.7572	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7545	Intermediate Similarity	NPD2296	Approved
0.7545	Intermediate Similarity	NPD5402	Approved
0.7531	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7529	Intermediate Similarity	NPD7074	Phase 3
0.7516	Intermediate Similarity	NPD2799	Discontinued
0.7483	Intermediate Similarity	NPD1470	Approved
0.7483	Intermediate Similarity	NPD1203	Approved
0.7471	Intermediate Similarity	NPD7054	Approved
0.7468	Intermediate Similarity	NPD2935	Discontinued
0.7468	Intermediate Similarity	NPD2313	Discontinued
0.7455	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.745	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.744	Intermediate Similarity	NPD3817	Phase 2
0.7439	Intermediate Similarity	NPD5403	Approved
0.7429	Intermediate Similarity	NPD7472	Approved
0.7423	Intermediate Similarity	NPD5401	Approved
0.7414	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7396	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD4628	Phase 3
0.7389	Intermediate Similarity	NPD6651	Approved
0.7386	Intermediate Similarity	NPD5953	Discontinued
0.7386	Intermediate Similarity	NPD6797	Phase 2
0.7384	Intermediate Similarity	NPD5711	Approved
0.7384	Intermediate Similarity	NPD5710	Approved
0.7372	Intermediate Similarity	NPD943	Approved
0.7362	Intermediate Similarity	NPD7390	Discontinued
0.7355	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7345	Intermediate Similarity	NPD7251	Discontinued
0.7333	Intermediate Similarity	NPD1201	Approved
0.7329	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7321	Intermediate Similarity	NPD6279	Approved
0.7321	Intermediate Similarity	NPD6280	Approved
0.7314	Intermediate Similarity	NPD3751	Discontinued
0.731	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD7808	Phase 3
0.7303	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7296	Intermediate Similarity	NPD3748	Approved
0.7296	Intermediate Similarity	NPD7033	Discontinued
0.7285	Intermediate Similarity	NPD9717	Approved
0.7285	Intermediate Similarity	NPD1608	Approved
0.7284	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7283	Intermediate Similarity	NPD6808	Phase 2
0.7283	Intermediate Similarity	NPD7229	Phase 3
0.7278	Intermediate Similarity	NPD1465	Phase 2
0.7273	Intermediate Similarity	NPD7286	Phase 2
0.7268	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7263	Intermediate Similarity	NPD8312	Approved
0.7263	Intermediate Similarity	NPD8313	Approved
0.7244	Intermediate Similarity	NPD3268	Approved
0.7226	Intermediate Similarity	NPD6832	Phase 2
0.7219	Intermediate Similarity	NPD1610	Phase 2
0.7219	Intermediate Similarity	NPD37	Approved
0.7215	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7215	Intermediate Similarity	NPD447	Suspended
0.7208	Intermediate Similarity	NPD2798	Approved
0.7193	Intermediate Similarity	NPD4966	Approved
0.7193	Intermediate Similarity	NPD4965	Approved
0.7193	Intermediate Similarity	NPD4967	Phase 2
0.7189	Intermediate Similarity	NPD4360	Phase 2
0.7189	Intermediate Similarity	NPD4363	Phase 3
0.7179	Intermediate Similarity	NPD4625	Phase 3
0.7158	Intermediate Similarity	NPD4287	Approved
0.7151	Intermediate Similarity	NPD4361	Phase 2
0.7151	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD2797	Approved
0.7135	Intermediate Similarity	NPD5616	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD411	Approved
0.7134	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD4908	Phase 1
0.711	Intermediate Similarity	NPD6234	Discontinued
0.7102	Intermediate Similarity	NPD4575	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD6002	Phase 3
0.7099	Intermediate Similarity	NPD6004	Phase 3
0.7099	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD6005	Phase 3
0.7095	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD17	Approved
0.7086	Intermediate Similarity	NPD3787	Discontinued
0.7081	Intermediate Similarity	NPD4308	Phase 3
0.7081	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7078	Intermediate Similarity	NPD1876	Approved
0.7066	Intermediate Similarity	NPD6273	Approved
0.7044	Intermediate Similarity	NPD1613	Approved
0.7044	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD1729	Discontinued
0.7032	Intermediate Similarity	NPD3266	Approved
0.7032	Intermediate Similarity	NPD3267	Approved
0.7029	Intermediate Similarity	NPD7199	Phase 2
0.7025	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD6844	Discontinued
0.7006	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD6780	Approved
0.7	Intermediate Similarity	NPD6777	Approved
0.7	Intermediate Similarity	NPD6779	Approved
0.7	Intermediate Similarity	NPD6778	Approved
0.7	Intermediate Similarity	NPD230	Phase 1
0.7	Intermediate Similarity	NPD6781	Approved
0.7	Intermediate Similarity	NPD6782	Approved
0.7	Intermediate Similarity	NPD6776	Approved
0.6987	Remote Similarity	NPD1019	Discontinued
0.6968	Remote Similarity	NPD1283	Approved
0.6961	Remote Similarity	NPD6764	Approved
0.6961	Remote Similarity	NPD6765	Approved
0.6959	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD8150	Discontinued
0.6954	Remote Similarity	NPD1548	Phase 1
0.6948	Remote Similarity	NPD3972	Approved
0.6933	Remote Similarity	NPD9493	Approved
0.6933	Remote Similarity	NPD405	Clinical (unspecified phase)
0.6927	Remote Similarity	NPD7228	Approved
0.6918	Remote Similarity	NPD3764	Approved
0.6911	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.691	Remote Similarity	NPD2403	Approved
0.6909	Remote Similarity	NPD2654	Approved
0.6903	Remote Similarity	NPD4749	Approved
0.6902	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6894	Remote Similarity	NPD6355	Discontinued
0.6891	Remote Similarity	NPD7696	Phase 3
0.6891	Remote Similarity	NPD7435	Discontinued
0.6891	Remote Similarity	NPD7698	Approved
0.6891	Remote Similarity	NPD7697	Approved
0.6888	Remote Similarity	NPD8151	Discontinued
0.6883	Remote Similarity	NPD422	Phase 1
0.6882	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.6868	Remote Similarity	NPD3658	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD7003	Approved
0.6856	Remote Similarity	NPD7870	Phase 2
0.6856	Remote Similarity	NPD7871	Phase 2
0.6854	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6848	Remote Similarity	NPD2424	Discontinued

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