NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	206.09
Volume:	214.82
LogP:	2.805
LogD:	2.169
LogS:	-3.114
# Rotatable Bonds:	1
TPSA:	35.53
# H-Bond Aceptor:	3
# H-Bond Donor:	0
# Rings:	2
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.66
Synthetic Accessibility Score:	2.754
Fsp3:	0.417
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:	-4.503
MDCK Permeability:	2.859240339603275e-05
Pgp-inhibitor:	0.007
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.004
30% Bioavailability (F30%):	0.009

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.406
Plasma Protein Binding (PPB):	88.6307144165039%
Volume Distribution (VD):	0.77
Pgp-substrate:	6.542165756225586%

ADMET: Metabolism

CYP1A2-inhibitor:	0.936
CYP1A2-substrate:	0.924
CYP2C19-inhibitor:	0.653
CYP2C19-substrate:	0.806
CYP2C9-inhibitor:	0.237
CYP2C9-substrate:	0.894
CYP2D6-inhibitor:	0.259
CYP2D6-substrate:	0.898
CYP3A4-inhibitor:	0.394
CYP3A4-substrate:	0.3

ADMET: Excretion

Clearance (CL):	12.01
Half-life (T1/2):	0.4

ADMET: Toxicity

hERG Blockers:	0.016
Human Hepatotoxicity (H-HT):	0.325
Drug-inuced Liver Injury (DILI):	0.54
AMES Toxicity:	0.167
Rat Oral Acute Toxicity:	0.027
Maximum Recommended Daily Dose:	0.047
Skin Sensitization:	0.565
Carcinogencity:	0.816
Eye Corrosion:	0.066
Eye Irritation:	0.839
Respiratory Toxicity:	0.248

Download Data

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

Natural Product: NPC470844

Natural Product ID:	NPC470844
*Common Name:**	3-5-Dimethyl-8-Methoxy-3,4-Dihydroisocoumarin
IUPAC Name:	8-methoxy-3,5-dimethyl-3,4-dihydroisochromen-1-one
Synonyms:
Standard InCHIKey:	PUHAIJJCXSKQQD-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C12H14O3/c1-7-4-5-10(14-3)11-9(7)6-8(2)15-12(11)13/h4-5,8H,6H2,1-3H3
SMILES:	COc1ccc(c2c1C(=O)OC(C2)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL226463
PubChem CID:	568998
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000123] Benzopyrans [CHEMONTID:0003411] 2-benzopyrans

*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
NPO33177	nodulisporium sp.	Species	Xylariaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12270179]
NPO33177	nodulisporium sp.	Species	Xylariaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12542359]
NPO33177	nodulisporium sp.	Species	Xylariaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17363259]
NPO33177	nodulisporium sp.	Species	Xylariaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25978520]

☑ 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	6

Activity Type	# Activity
Individual Protein	3
Others	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2216	Individual Protein	DNA polymerase beta	Rattus norvegicus	IC50	>	1000000.0	nM	PMID[564541]
NPT4232	Individual Protein	DNA polymerase delta subunit 1	Homo sapiens	IC50	>	1000000.0	nM	PMID[564541]
NPT3732	Individual Protein	DNA polymerase lambda	Homo sapiens	IC50	=	49000.0	nM	PMID[564541]
NPT2	Others	Unspecified		IC50	>	1000000.0	nM	PMID[564541]

☑ 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 NPC470844 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	368
0.1-0.2	1646
0.2-0.3	3824
0.3-0.4	9076
0.4-0.5	9350
0.5-0.6	3656
0.6-0.7	7448
0.7-0.8	6258
0.8-0.85	937
0.85-0.9	125
0.9-0.95	7
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9609	High Similarity	NPC473271
0.9323	High Similarity	NPC291454
0.9058	High Similarity	NPC469579
0.9044	High Similarity	NPC221104
0.8993	High Similarity	NPC469542
0.8993	High Similarity	NPC471643
0.8993	High Similarity	NPC471639
0.8986	High Similarity	NPC470842
0.8947	High Similarity	NPC470831
0.8947	High Similarity	NPC214702
0.8929	High Similarity	NPC470932
0.8865	High Similarity	NPC473692
0.8849	High Similarity	NPC67650
0.8849	High Similarity	NPC1704
0.8841	High Similarity	NPC88269
0.8832	High Similarity	NPC301915
0.8832	High Similarity	NPC135837
0.8832	High Similarity	NPC261292
0.8824	High Similarity	NPC142027
0.8824	High Similarity	NPC27407
0.8803	High Similarity	NPC471346
0.8794	High Similarity	NPC184702
0.8794	High Similarity	NPC151607
0.8794	High Similarity	NPC42540
0.8786	High Similarity	NPC471644
0.8786	High Similarity	NPC471640
0.8786	High Similarity	NPC474385
0.8786	High Similarity	NPC297985
0.8777	High Similarity	NPC165172
0.8777	High Similarity	NPC472601
0.8777	High Similarity	NPC472600
0.8759	High Similarity	NPC235115
0.875	High Similarity	NPC311339
0.8723	High Similarity	NPC159721
0.8723	High Similarity	NPC51106
0.8723	High Similarity	NPC472006
0.8714	High Similarity	NPC475730
0.8714	High Similarity	NPC472604
0.8714	High Similarity	NPC472605
0.8714	High Similarity	NPC472603
0.8702	High Similarity	NPC470163
0.8702	High Similarity	NPC470162
0.8686	High Similarity	NPC182496
0.8686	High Similarity	NPC180905
0.8671	High Similarity	NPC163846
0.8671	High Similarity	NPC225173
0.8671	High Similarity	NPC473927
0.8671	High Similarity	NPC260946
0.8662	High Similarity	NPC277426
0.8662	High Similarity	NPC210425
0.8662	High Similarity	NPC280404
0.8662	High Similarity	NPC86373
0.8652	High Similarity	NPC250755
0.8643	High Similarity	NPC155205
0.8633	High Similarity	NPC233780
0.8633	High Similarity	NPC472602
0.863	High Similarity	NPC215921
0.863	High Similarity	NPC70016
0.8623	High Similarity	NPC50455
0.8621	High Similarity	NPC77325
0.8621	High Similarity	NPC237440
0.8621	High Similarity	NPC4423
0.8621	High Similarity	NPC270160
0.8611	High Similarity	NPC125801
0.8601	High Similarity	NPC472034
0.8592	High Similarity	NPC472610
0.8592	High Similarity	NPC471731
0.8592	High Similarity	NPC215451
0.8592	High Similarity	NPC277369
0.8582	High Similarity	NPC470856
0.8582	High Similarity	NPC158634
0.8582	High Similarity	NPC90411
0.8582	High Similarity	NPC149533
0.8582	High Similarity	NPC53649
0.8571	High Similarity	NPC36414
0.8571	High Similarity	NPC268052
0.8571	High Similarity	NPC271681
0.8571	High Similarity	NPC295646
0.8571	High Similarity	NPC32360
0.8562	High Similarity	NPC119929
0.8561	High Similarity	NPC70380
0.8552	High Similarity	NPC37139
0.8542	High Similarity	NPC472033
0.8542	High Similarity	NPC267509
0.8542	High Similarity	NPC107625
0.8542	High Similarity	NPC473023
0.854	High Similarity	NPC153783
0.8531	High Similarity	NPC27106
0.8521	High Similarity	NPC82913
0.8521	High Similarity	NPC471733
0.8514	High Similarity	NPC472799
0.8511	High Similarity	NPC109007
0.8507	High Similarity	NPC293387
0.8503	High Similarity	NPC473732
0.85	High Similarity	NPC33144
0.85	High Similarity	NPC191835
0.85	High Similarity	NPC197666
0.85	High Similarity	NPC126739
0.85	High Similarity	NPC253616
0.85	High Similarity	NPC212693
0.85	High Similarity	NPC94248
0.85	High Similarity	NPC259685
0.85	High Similarity	NPC478200
0.8496	Intermediate Similarity	NPC165556
0.8493	Intermediate Similarity	NPC476684
0.8493	Intermediate Similarity	NPC291049
0.8493	Intermediate Similarity	NPC233267
0.8489	Intermediate Similarity	NPC160425
0.8489	Intermediate Similarity	NPC158481
0.8483	Intermediate Similarity	NPC210320
0.8483	Intermediate Similarity	NPC52106
0.8483	Intermediate Similarity	NPC472036
0.8478	Intermediate Similarity	NPC175943
0.8478	Intermediate Similarity	NPC247743
0.8472	Intermediate Similarity	NPC32470
0.8472	Intermediate Similarity	NPC49282
0.8472	Intermediate Similarity	NPC171656
0.8472	Intermediate Similarity	NPC134621
0.8472	Intermediate Similarity	NPC294365
0.8467	Intermediate Similarity	NPC470160
0.8462	Intermediate Similarity	NPC478202
0.8456	Intermediate Similarity	NPC109778
0.8451	Intermediate Similarity	NPC478217
0.8451	Intermediate Similarity	NPC37530
0.8451	Intermediate Similarity	NPC313123
0.8451	Intermediate Similarity	NPC220106
0.8446	Intermediate Similarity	NPC475116
0.8446	Intermediate Similarity	NPC167903
0.8446	Intermediate Similarity	NPC273483
0.844	Intermediate Similarity	NPC105456
0.844	Intermediate Similarity	NPC275356
0.844	Intermediate Similarity	NPC139634
0.8435	Intermediate Similarity	NPC474660
0.8435	Intermediate Similarity	NPC469619
0.8435	Intermediate Similarity	NPC470107
0.8435	Intermediate Similarity	NPC158866
0.8435	Intermediate Similarity	NPC179178
0.8435	Intermediate Similarity	NPC475460
0.8435	Intermediate Similarity	NPC150928
0.8435	Intermediate Similarity	NPC469670
0.8429	Intermediate Similarity	NPC71256
0.8429	Intermediate Similarity	NPC194579
0.8429	Intermediate Similarity	NPC472516
0.8429	Intermediate Similarity	NPC268081
0.8425	Intermediate Similarity	NPC73411
0.8425	Intermediate Similarity	NPC240622
0.8425	Intermediate Similarity	NPC471641
0.8425	Intermediate Similarity	NPC153417
0.8425	Intermediate Similarity	NPC215711
0.8425	Intermediate Similarity	NPC105415
0.8425	Intermediate Similarity	NPC240253
0.8425	Intermediate Similarity	NPC471642
0.8414	Intermediate Similarity	NPC237208
0.8414	Intermediate Similarity	NPC470357
0.8406	Intermediate Similarity	NPC229646
0.8403	Intermediate Similarity	NPC66404
0.8403	Intermediate Similarity	NPC95123
0.8403	Intermediate Similarity	NPC189650
0.84	Intermediate Similarity	NPC301897
0.84	Intermediate Similarity	NPC227062
0.8394	Intermediate Similarity	NPC219892
0.8394	Intermediate Similarity	NPC189823
0.8394	Intermediate Similarity	NPC477412
0.8392	Intermediate Similarity	NPC96692
0.8392	Intermediate Similarity	NPC322112
0.8392	Intermediate Similarity	NPC105648
0.8392	Intermediate Similarity	NPC94076
0.8392	Intermediate Similarity	NPC182255
0.8389	Intermediate Similarity	NPC281477
0.8389	Intermediate Similarity	NPC192189
0.8382	Intermediate Similarity	NPC170546
0.8382	Intermediate Similarity	NPC66246
0.838	Intermediate Similarity	NPC11566
0.838	Intermediate Similarity	NPC99441
0.838	Intermediate Similarity	NPC472515
0.838	Intermediate Similarity	NPC136095
0.838	Intermediate Similarity	NPC158472
0.838	Intermediate Similarity	NPC168471
0.8378	Intermediate Similarity	NPC232645
0.8378	Intermediate Similarity	NPC133856
0.8378	Intermediate Similarity	NPC240768
0.8378	Intermediate Similarity	NPC72958
0.8378	Intermediate Similarity	NPC200773
0.8372	Intermediate Similarity	NPC217423
0.837	Intermediate Similarity	NPC37512
0.8367	Intermediate Similarity	NPC164299
0.8357	Intermediate Similarity	NPC242712
0.8357	Intermediate Similarity	NPC99854
0.8356	Intermediate Similarity	NPC471734
0.8356	Intermediate Similarity	NPC8817
0.8356	Intermediate Similarity	NPC14098
0.8356	Intermediate Similarity	NPC137296
0.8345	Intermediate Similarity	NPC75694
0.8345	Intermediate Similarity	NPC312789
0.8345	Intermediate Similarity	NPC29577
0.8333	Intermediate Similarity	NPC82592
0.8333	Intermediate Similarity	NPC199926
0.8333	Intermediate Similarity	NPC89625
0.8333	Intermediate Similarity	NPC149618
0.8333	Intermediate Similarity	NPC167663

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 NPC470844 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	342
0.1-0.2	984
0.2-0.3	1580
0.3-0.4	2561
0.4-0.5	1825
0.5-0.6	1203
0.6-0.7	473
0.7-0.8	170
0.8-0.85	9
0.85-0.9	3
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8705	High Similarity	NPD970	Clinical (unspecified phase)
0.8639	High Similarity	NPD7819	Suspended
0.8345	Intermediate Similarity	NPD2533	Approved
0.8345	Intermediate Similarity	NPD2532	Approved
0.8345	Intermediate Similarity	NPD2534	Approved
0.8298	Intermediate Similarity	NPD2796	Approved
0.8252	Intermediate Similarity	NPD1243	Approved
0.8207	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.8169	Intermediate Similarity	NPD2935	Discontinued
0.8146	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8112	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8112	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8108	Intermediate Similarity	NPD920	Approved
0.8106	Intermediate Similarity	NPD5691	Approved
0.8095	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.8071	Intermediate Similarity	NPD1240	Approved
0.806	Intermediate Similarity	NPD1281	Approved
0.8056	Intermediate Similarity	NPD1549	Phase 2
0.8045	Intermediate Similarity	NPD17	Approved
0.8026	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8013	Intermediate Similarity	NPD7411	Suspended
0.7987	Intermediate Similarity	NPD7075	Discontinued
0.7986	Intermediate Similarity	NPD2346	Discontinued
0.7972	Intermediate Similarity	NPD3748	Approved
0.7972	Intermediate Similarity	NPD1510	Phase 2
0.7958	Intermediate Similarity	NPD1607	Approved
0.7935	Intermediate Similarity	NPD919	Approved
0.7926	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7914	Intermediate Similarity	NPD6832	Phase 2
0.7905	Intermediate Similarity	NPD6799	Approved
0.7898	Intermediate Similarity	NPD6232	Discontinued
0.7887	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7885	Intermediate Similarity	NPD5494	Approved
0.7883	Intermediate Similarity	NPD1283	Approved
0.7881	Intermediate Similarity	NPD3226	Approved
0.7877	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7868	Intermediate Similarity	NPD1608	Approved
0.7857	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7852	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7847	Intermediate Similarity	NPD2799	Discontinued
0.7843	Intermediate Similarity	NPD1934	Approved
0.7843	Intermediate Similarity	NPD6801	Discontinued
0.7834	Intermediate Similarity	NPD6959	Discontinued
0.7829	Intermediate Similarity	NPD6599	Discontinued
0.7829	Intermediate Similarity	NPD4380	Phase 2
0.7785	Intermediate Similarity	NPD5711	Approved
0.7785	Intermediate Similarity	NPD5710	Approved
0.7778	Intermediate Similarity	NPD4626	Approved
0.777	Intermediate Similarity	NPD1019	Discontinued
0.7764	Intermediate Similarity	NPD5844	Phase 1
0.7761	Intermediate Similarity	NPD9545	Approved
0.775	Intermediate Similarity	NPD7473	Discontinued
0.7742	Intermediate Similarity	NPD3817	Phase 2
0.7737	Intermediate Similarity	NPD9717	Approved
0.7704	Intermediate Similarity	NPD1651	Approved
0.7703	Intermediate Similarity	NPD4628	Phase 3
0.7703	Intermediate Similarity	NPD3750	Approved
0.7692	Intermediate Similarity	NPD2979	Phase 3
0.7692	Intermediate Similarity	NPD7768	Phase 2
0.7688	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7676	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7671	Intermediate Similarity	NPD2438	Suspended
0.7671	Intermediate Similarity	NPD1551	Phase 2
0.7647	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7643	Intermediate Similarity	NPD3749	Approved
0.7612	Intermediate Similarity	NPD9493	Approved
0.7584	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7571	Intermediate Similarity	NPD1203	Approved
0.7552	Intermediate Similarity	NPD2313	Discontinued
0.7552	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7552	Intermediate Similarity	NPD411	Approved
0.755	Intermediate Similarity	NPD1511	Approved
0.7519	Intermediate Similarity	NPD1241	Discontinued
0.7518	Intermediate Similarity	NPD2798	Approved
0.7517	Intermediate Similarity	NPD1933	Approved
0.7517	Intermediate Similarity	NPD2800	Approved
0.7517	Intermediate Similarity	NPD447	Suspended
0.75	Intermediate Similarity	NPD1471	Phase 3
0.75	Intermediate Similarity	NPD1247	Approved
0.75	Intermediate Similarity	NPD1876	Approved
0.75	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7482	Intermediate Similarity	NPD3972	Approved
0.7468	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7467	Intermediate Similarity	NPD7003	Approved
0.7451	Intermediate Similarity	NPD6273	Approved
0.7451	Intermediate Similarity	NPD1512	Approved
0.7447	Intermediate Similarity	NPD3266	Approved
0.7447	Intermediate Similarity	NPD1164	Approved
0.7447	Intermediate Similarity	NPD3267	Approved
0.7432	Intermediate Similarity	NPD5406	Approved
0.7432	Intermediate Similarity	NPD5405	Approved
0.7432	Intermediate Similarity	NPD2531	Phase 2
0.7432	Intermediate Similarity	NPD5408	Approved
0.7432	Intermediate Similarity	NPD4477	Approved
0.7432	Intermediate Similarity	NPD5404	Approved
0.7432	Intermediate Similarity	NPD4476	Approved
0.7431	Intermediate Similarity	NPD1296	Phase 2
0.7427	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7421	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.741	Intermediate Similarity	NPD1201	Approved
0.7403	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7397	Intermediate Similarity	NPD230	Phase 1
0.7391	Intermediate Similarity	NPD1778	Approved
0.7386	Intermediate Similarity	NPD5401	Approved
0.7383	Intermediate Similarity	NPD2344	Approved
0.7378	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD7033	Discontinued
0.7362	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7362	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7362	Intermediate Similarity	NPD6166	Phase 2
0.7358	Intermediate Similarity	NPD3882	Suspended
0.7351	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7347	Intermediate Similarity	NPD6651	Approved
0.7342	Intermediate Similarity	NPD2801	Approved
0.7342	Intermediate Similarity	NPD1465	Phase 2
0.7333	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD4307	Phase 2
0.7324	Intermediate Similarity	NPD2797	Approved
0.731	Intermediate Similarity	NPD3764	Approved
0.7305	Intermediate Similarity	NPD6559	Discontinued
0.7296	Intermediate Similarity	NPD5402	Approved
0.729	Intermediate Similarity	NPD5403	Approved
0.7289	Intermediate Similarity	NPD7074	Phase 3
0.7287	Intermediate Similarity	NPD9261	Approved
0.7286	Intermediate Similarity	NPD1611	Approved
0.7286	Intermediate Similarity	NPD422	Phase 1
0.7285	Intermediate Similarity	NPD2654	Approved
0.7267	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.726	Intermediate Similarity	NPD8032	Phase 2
0.7246	Intermediate Similarity	NPD5953	Discontinued
0.7239	Intermediate Similarity	NPD7229	Phase 3
0.7229	Intermediate Similarity	NPD7054	Approved
0.7219	Intermediate Similarity	NPD8312	Approved
0.7219	Intermediate Similarity	NPD8313	Approved
0.7215	Intermediate Similarity	NPD5890	Approved
0.7215	Intermediate Similarity	NPD5889	Approved
0.7211	Intermediate Similarity	NPD4060	Phase 1
0.7209	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7208	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7203	Intermediate Similarity	NPD1470	Approved
0.72	Intermediate Similarity	NPD6100	Approved
0.72	Intermediate Similarity	NPD6099	Approved
0.7197	Intermediate Similarity	NPD7458	Discontinued
0.7195	Intermediate Similarity	NPD3926	Phase 2
0.7192	Intermediate Similarity	NPD3268	Approved
0.719	Intermediate Similarity	NPD2309	Approved
0.7188	Intermediate Similarity	NPD5353	Approved
0.7186	Intermediate Similarity	NPD7472	Approved
0.7169	Intermediate Similarity	NPD3818	Discontinued
0.7169	Intermediate Similarity	NPD7177	Discontinued
0.7164	Intermediate Similarity	NPD2181	Clinical (unspecified phase)
0.7162	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7162	Intermediate Similarity	NPD5124	Phase 1
0.7162	Intermediate Similarity	NPD6355	Discontinued
0.716	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD6005	Phase 3
0.7152	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD6004	Phase 3
0.7152	Intermediate Similarity	NPD6002	Phase 3
0.7152	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6797	Phase 2
0.7134	Intermediate Similarity	NPD6808	Phase 2
0.7133	Intermediate Similarity	NPD4308	Phase 3
0.7126	Intermediate Similarity	NPD7286	Phase 2
0.7121	Intermediate Similarity	NPD3134	Approved
0.7107	Intermediate Similarity	NPD6386	Approved
0.7107	Intermediate Similarity	NPD6385	Approved
0.7105	Intermediate Similarity	NPD2897	Discontinued
0.7103	Intermediate Similarity	NPD9494	Approved
0.7101	Intermediate Similarity	NPD7251	Discontinued
0.7101	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD7390	Discontinued
0.7095	Intermediate Similarity	NPD943	Approved
0.7095	Intermediate Similarity	NPD3142	Approved
0.7095	Intermediate Similarity	NPD3140	Approved
0.7093	Intermediate Similarity	NPD8150	Discontinued
0.7091	Intermediate Similarity	NPD5242	Approved
0.7081	Intermediate Similarity	NPD4288	Approved
0.7078	Intermediate Similarity	NPD3887	Approved
0.7075	Intermediate Similarity	NPD6798	Discontinued
0.7073	Intermediate Similarity	NPD7199	Phase 2
0.7071	Intermediate Similarity	NPD5585	Approved
0.7068	Intermediate Similarity	NPD9263	Approved
0.7068	Intermediate Similarity	NPD1358	Approved
0.7068	Intermediate Similarity	NPD9264	Approved
0.7068	Intermediate Similarity	NPD9267	Approved
0.7063	Intermediate Similarity	NPD37	Approved
0.7059	Intermediate Similarity	NPD7808	Phase 3
0.7055	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7044	Intermediate Similarity	NPD6585	Discontinued
0.7042	Intermediate Similarity	NPD1610	Phase 2
0.7037	Intermediate Similarity	NPD4965	Approved
0.7037	Intermediate Similarity	NPD4966	Approved
0.7037	Intermediate Similarity	NPD4967	Phase 2
0.7032	Intermediate Similarity	NPD6652	Clinical (unspecified phase)
0.702	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD8455	Phase 2

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