NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	250.08
Volume:	247.06
LogP:	2.291
LogD:	1.292
LogS:	-3.269
# Rotatable Bonds:	2
TPSA:	72.83
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.806
Synthetic Accessibility Score:	3.287
Fsp3:	0.385
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:	-4.63
MDCK Permeability:	1.5284183973562904e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.174
Human Intestinal Absorption (HIA):	0.013
20% Bioavailability (F20%):	0.029
30% Bioavailability (F30%):	0.007

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.742
Plasma Protein Binding (PPB):	94.69356536865234%
Volume Distribution (VD):	0.721
Pgp-substrate:	6.439235687255859%

ADMET: Metabolism

CYP1A2-inhibitor:	0.463
CYP1A2-substrate:	0.889
CYP2C19-inhibitor:	0.191
CYP2C19-substrate:	0.851
CYP2C9-inhibitor:	0.258
CYP2C9-substrate:	0.897
CYP2D6-inhibitor:	0.076
CYP2D6-substrate:	0.554
CYP3A4-inhibitor:	0.274
CYP3A4-substrate:	0.551

ADMET: Excretion

Clearance (CL):	12.508
Half-life (T1/2):	0.811

ADMET: Toxicity

hERG Blockers:	0.019
Human Hepatotoxicity (H-HT):	0.146
Drug-inuced Liver Injury (DILI):	0.332
AMES Toxicity:	0.092
Rat Oral Acute Toxicity:	0.146
Maximum Recommended Daily Dose:	0.233
Skin Sensitization:	0.211
Carcinogencity:	0.127
Eye Corrosion:	0.429
Eye Irritation:	0.942
Respiratory Toxicity:	0.247

Download Data

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

Natural Product: NPC473692

Natural Product ID:	NPC473692
*Common Name:**	4-Acetyl-8-Hydroxy-6-Methoxy-5-Methylisocoumarin
IUPAC Name:	4-acetyl-8-hydroxy-6-methoxy-5-methyl-3,4-dihydroisochromen-1-one
Synonyms:
Standard InCHIKey:	WDZKVEWQIUSSSX-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C13H14O5/c1-6-10(17-3)4-9(15)12-11(6)8(7(2)14)5-18-13(12)16/h4,8,15H,5H2,1-3H3
SMILES:	CC1=C(C=C(C2=C1C(COC2=O)C(=O)C)O)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL449315
PubChem CID:	10705785
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
NPO10303	Cercophora areolata	Species	Lasiosphaeriaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8792624]
NPO10303	Cercophora areolata	Species	Lasiosphaeriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
Others	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT3095	Organism	Sordaria fimicola	Sordaria fimicola	Activity	=	46.0	%	PMID[531721]

☑ 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 NPC473692 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	333
0.1-0.2	1631
0.2-0.3	3905
0.3-0.4	8976
0.4-0.5	9568
0.5-0.6	3657
0.6-0.7	6017
0.7-0.8	5882
0.8-0.85	2064
0.85-0.9	588
0.9-0.95	75
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9424	High Similarity	NPC88269
0.932	High Similarity	NPC192189
0.9296	High Similarity	NPC469542
0.9291	High Similarity	NPC472603
0.9281	High Similarity	NPC135837
0.9236	High Similarity	NPC260946
0.922	High Similarity	NPC165172
0.922	High Similarity	NPC472601
0.922	High Similarity	NPC472600
0.9209	High Similarity	NPC50455
0.9178	High Similarity	NPC198927
0.9167	High Similarity	NPC312789
0.9167	High Similarity	NPC472034
0.9161	High Similarity	NPC472006
0.9155	High Similarity	NPC472604
0.9155	High Similarity	NPC1704
0.9155	High Similarity	NPC472605
0.9155	High Similarity	NPC67650
0.9149	High Similarity	NPC92655
0.9137	High Similarity	NPC180905
0.9137	High Similarity	NPC182496
0.911	High Similarity	NPC153417
0.911	High Similarity	NPC240253
0.911	High Similarity	NPC471642
0.911	High Similarity	NPC471641
0.911	High Similarity	NPC240622
0.9103	High Similarity	NPC472033
0.9091	High Similarity	NPC82913
0.9091	High Similarity	NPC469579
0.9078	High Similarity	NPC221104
0.9071	High Similarity	NPC235115
0.906	High Similarity	NPC472799
0.9048	High Similarity	NPC4423
0.9048	High Similarity	NPC77325
0.9041	High Similarity	NPC472036
0.9041	High Similarity	NPC14098
0.9028	High Similarity	NPC159721
0.9028	High Similarity	NPC472610
0.9028	High Similarity	NPC471643
0.9028	High Similarity	NPC51106
0.9028	High Similarity	NPC471639
0.9028	High Similarity	NPC478202
0.9021	High Similarity	NPC90411
0.9021	High Similarity	NPC478217
0.9021	High Similarity	NPC313123
0.9021	High Similarity	NPC37530
0.9021	High Similarity	NPC307990
0.9021	High Similarity	NPC16455
0.9014	High Similarity	NPC57380
0.9014	High Similarity	NPC275356
0.9014	High Similarity	NPC268052
0.9007	High Similarity	NPC245058
0.8993	High Similarity	NPC153783
0.8986	High Similarity	NPC119929
0.8986	High Similarity	NPC158866
0.8986	High Similarity	NPC60413
0.8986	High Similarity	NPC150928
0.8973	High Similarity	NPC107625
0.8973	High Similarity	NPC267509
0.8973	High Similarity	NPC225173
0.8973	High Similarity	NPC163846
0.8966	High Similarity	NPC151607
0.8966	High Similarity	NPC42540
0.8958	High Similarity	NPC322112
0.8958	High Similarity	NPC250755
0.8958	High Similarity	NPC94076
0.8958	High Similarity	NPC182255
0.8958	High Similarity	NPC474385
0.8951	High Similarity	NPC99441
0.8944	High Similarity	NPC191835
0.8944	High Similarity	NPC472602
0.8936	High Similarity	NPC291454
0.8936	High Similarity	NPC158481
0.8929	High Similarity	NPC175943
0.8926	High Similarity	NPC133856
0.8921	High Similarity	NPC27490
0.8919	High Similarity	NPC291049
0.8919	High Similarity	NPC270160
0.8919	High Similarity	NPC237440
0.8919	High Similarity	NPC6923
0.8919	High Similarity	NPC233267
0.8912	High Similarity	NPC125801
0.8904	High Similarity	NPC134621
0.8904	High Similarity	NPC32470
0.8897	High Similarity	NPC310340
0.8897	High Similarity	NPC471731
0.8897	High Similarity	NPC84266
0.8889	High Similarity	NPC478201
0.8889	High Similarity	NPC220106
0.8889	High Similarity	NPC53649
0.8889	High Similarity	NPC472035
0.8889	High Similarity	NPC475730
0.8889	High Similarity	NPC275734
0.8889	High Similarity	NPC470842
0.8882	High Similarity	NPC263483
0.8881	High Similarity	NPC32360
0.8874	High Similarity	NPC89625
0.8874	High Similarity	NPC149618
0.8873	High Similarity	NPC149372
0.8873	High Similarity	NPC178467
0.8873	High Similarity	NPC70380
0.8873	High Similarity	NPC65837
0.8873	High Similarity	NPC474771
0.8873	High Similarity	NPC194579
0.8873	High Similarity	NPC474849
0.8867	High Similarity	NPC87708
0.8867	High Similarity	NPC167903
0.8867	High Similarity	NPC273483
0.8867	High Similarity	NPC271681
0.8865	High Similarity	NPC470844
0.8859	High Similarity	NPC470107
0.8859	High Similarity	NPC325983
0.8859	High Similarity	NPC179178
0.8859	High Similarity	NPC202595
0.8851	High Similarity	NPC37139
0.8851	High Similarity	NPC105415
0.8849	High Similarity	NPC219892
0.8849	High Similarity	NPC189823
0.8849	High Similarity	NPC324482
0.8844	High Similarity	NPC237208
0.8844	High Similarity	NPC473023
0.8841	High Similarity	NPC230818
0.8836	High Similarity	NPC210425
0.8836	High Similarity	NPC95123
0.8836	High Similarity	NPC277426
0.8836	High Similarity	NPC86373
0.8836	High Similarity	NPC280404
0.8836	High Similarity	NPC66404
0.8828	High Similarity	NPC471733
0.8828	High Similarity	NPC471644
0.8828	High Similarity	NPC471640
0.8828	High Similarity	NPC105648
0.8819	High Similarity	NPC155205
0.8816	High Similarity	NPC4547
0.8811	High Similarity	NPC212693
0.8811	High Similarity	NPC478200
0.8811	High Similarity	NPC472403
0.8811	High Similarity	NPC94248
0.8811	High Similarity	NPC475974
0.8811	High Similarity	NPC33144
0.8803	High Similarity	NPC156967
0.8803	High Similarity	NPC242712
0.8803	High Similarity	NPC60667
0.88	High Similarity	NPC232645
0.88	High Similarity	NPC215921
0.88	High Similarity	NPC72958
0.88	High Similarity	NPC70016
0.8784	High Similarity	NPC22005
0.8784	High Similarity	NPC210320
0.8784	High Similarity	NPC7943
0.8784	High Similarity	NPC123202
0.8777	High Similarity	NPC84772
0.8776	High Similarity	NPC28632
0.8776	High Similarity	NPC75694
0.8776	High Similarity	NPC117716
0.8776	High Similarity	NPC470674
0.8776	High Similarity	NPC271288
0.8776	High Similarity	NPC29577
0.8776	High Similarity	NPC470673
0.8774	High Similarity	NPC473022
0.8766	High Similarity	NPC243701
0.8759	High Similarity	NPC477272
0.8759	High Similarity	NPC158634
0.875	High Similarity	NPC247409
0.875	High Similarity	NPC474487
0.875	High Similarity	NPC52358
0.875	High Similarity	NPC470672
0.875	High Similarity	NPC139634
0.875	High Similarity	NPC105456
0.875	High Similarity	NPC474655
0.875	High Similarity	NPC474504
0.875	High Similarity	NPC470671
0.8742	High Similarity	NPC175978
0.8742	High Similarity	NPC217447
0.8741	High Similarity	NPC222633
0.8741	High Similarity	NPC156910
0.8732	High Similarity	NPC125920
0.8732	High Similarity	NPC27407
0.8725	High Similarity	NPC256672
0.8725	High Similarity	NPC27221
0.8725	High Similarity	NPC2569
0.8725	High Similarity	NPC215711
0.8725	High Similarity	NPC7025
0.8725	High Similarity	NPC73411
0.8725	High Similarity	NPC172329
0.8723	High Similarity	NPC285054
0.8723	High Similarity	NPC48036
0.8716	High Similarity	NPC138978
0.8716	High Similarity	NPC473132
0.8716	High Similarity	NPC470676
0.8716	High Similarity	NPC473135
0.8716	High Similarity	NPC290133
0.8716	High Similarity	NPC24136
0.8716	High Similarity	NPC25844
0.8716	High Similarity	NPC187282
0.8707	High Similarity	NPC126882
0.8707	High Similarity	NPC210966
0.8707	High Similarity	NPC475201
0.8707	High Similarity	NPC19896
0.8707	High Similarity	NPC478203

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 NPC473692 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	304
0.1-0.2	1022
0.2-0.3	1797
0.3-0.4	2618
0.4-0.5	1766
0.5-0.6	1108
0.6-0.7	359
0.7-0.8	143
0.8-0.85	25
0.85-0.9	7
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9286	High Similarity	NPD970	Clinical (unspecified phase)
0.8808	High Similarity	NPD7819	Suspended
0.8776	High Similarity	NPD2534	Approved
0.8776	High Similarity	NPD2532	Approved
0.8776	High Similarity	NPD2533	Approved
0.8553	High Similarity	NPD7411	Suspended
0.8506	High Similarity	NPD8443	Clinical (unspecified phase)
0.8425	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8425	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8414	Intermediate Similarity	NPD1510	Phase 2
0.8392	Intermediate Similarity	NPD1240	Approved
0.8367	Intermediate Similarity	NPD1549	Phase 2
0.8354	Intermediate Similarity	NPD6959	Discontinued
0.8323	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8313	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.828	Intermediate Similarity	NPD7075	Discontinued
0.8278	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8276	Intermediate Similarity	NPD1607	Approved
0.8261	Intermediate Similarity	NPD7473	Discontinued
0.8205	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8188	Intermediate Similarity	NPD2800	Approved
0.8187	Intermediate Similarity	NPD5711	Approved
0.8187	Intermediate Similarity	NPD6232	Discontinued
0.8187	Intermediate Similarity	NPD5710	Approved
0.8151	Intermediate Similarity	NPD6651	Approved
0.8141	Intermediate Similarity	NPD1934	Approved
0.8133	Intermediate Similarity	NPD3750	Approved
0.8129	Intermediate Similarity	NPD4380	Phase 2
0.8108	Intermediate Similarity	NPD2935	Discontinued
0.8067	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.8067	Intermediate Similarity	NPD1243	Approved
0.8065	Intermediate Similarity	NPD3226	Approved
0.8052	Intermediate Similarity	NPD920	Approved
0.805	Intermediate Similarity	NPD3749	Approved
0.8041	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.8025	Intermediate Similarity	NPD6801	Discontinued
0.8013	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7987	Intermediate Similarity	NPD7768	Phase 2
0.7987	Intermediate Similarity	NPD1551	Phase 2
0.7974	Intermediate Similarity	NPD6799	Approved
0.7974	Intermediate Similarity	NPD1511	Approved
0.7922	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7908	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7898	Intermediate Similarity	NPD6599	Discontinued
0.7895	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7871	Intermediate Similarity	NPD1512	Approved
0.7867	Intermediate Similarity	NPD2796	Approved
0.7862	Intermediate Similarity	NPD1465	Phase 2
0.7838	Intermediate Similarity	NPD230	Phase 1
0.7831	Intermediate Similarity	NPD5844	Phase 1
0.7815	Intermediate Similarity	NPD2346	Discontinued
0.7812	Intermediate Similarity	NPD3817	Phase 2
0.7806	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.78	Intermediate Similarity	NPD2799	Discontinued
0.78	Intermediate Similarity	NPD3748	Approved
0.7778	Intermediate Similarity	NPD919	Approved
0.7764	Intermediate Similarity	NPD3882	Suspended
0.7764	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7755	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.775	Intermediate Similarity	NPD2801	Approved
0.7748	Intermediate Similarity	NPD6100	Approved
0.7748	Intermediate Similarity	NPD6099	Approved
0.773	Intermediate Similarity	NPD5494	Approved
0.7716	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7651	Intermediate Similarity	NPD6166	Phase 2
0.7651	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7651	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7633	Intermediate Similarity	NPD5953	Discontinued
0.7628	Intermediate Similarity	NPD7390	Discontinued
0.7619	Intermediate Similarity	NPD7286	Phase 2
0.7619	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7589	Intermediate Similarity	NPD9545	Approved
0.7588	Intermediate Similarity	NPD6559	Discontinued
0.7586	Intermediate Similarity	NPD1283	Approved
0.7576	Intermediate Similarity	NPD1247	Approved
0.7574	Intermediate Similarity	NPD7074	Phase 3
0.7569	Intermediate Similarity	NPD9717	Approved
0.7569	Intermediate Similarity	NPD1608	Approved
0.7534	Intermediate Similarity	NPD1203	Approved
0.7533	Intermediate Similarity	NPD943	Approved
0.7517	Intermediate Similarity	NPD3268	Approved
0.7515	Intermediate Similarity	NPD7054	Approved
0.75	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD422	Phase 1
0.7471	Intermediate Similarity	NPD7472	Approved
0.7456	Intermediate Similarity	NPD3818	Discontinued
0.7451	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7447	Intermediate Similarity	NPD9493	Approved
0.7442	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7442	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7436	Intermediate Similarity	NPD4628	Phase 3
0.7427	Intermediate Similarity	NPD6797	Phase 2
0.7425	Intermediate Similarity	NPD7229	Phase 3
0.7403	Intermediate Similarity	NPD5408	Approved
0.7403	Intermediate Similarity	NPD5404	Approved
0.7403	Intermediate Similarity	NPD5405	Approved
0.7403	Intermediate Similarity	NPD5406	Approved
0.74	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.74	Intermediate Similarity	NPD411	Approved
0.74	Intermediate Similarity	NPD2313	Discontinued
0.74	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7384	Intermediate Similarity	NPD7251	Discontinued
0.7379	Intermediate Similarity	NPD1201	Approved
0.7379	Intermediate Similarity	NPD1610	Phase 2
0.7379	Intermediate Similarity	NPD1281	Approved
0.7378	Intermediate Similarity	NPD5402	Approved
0.7375	Intermediate Similarity	NPD5403	Approved
0.7368	Intermediate Similarity	NPD447	Suspended
0.7368	Intermediate Similarity	NPD5124	Phase 1
0.7368	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7362	Intermediate Similarity	NPD37	Approved
0.7361	Intermediate Similarity	NPD17	Approved
0.7361	Intermediate Similarity	NPD4626	Approved
0.7358	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7358	Intermediate Similarity	NPD5401	Approved
0.7355	Intermediate Similarity	NPD2344	Approved
0.7349	Intermediate Similarity	NPD6234	Discontinued
0.7341	Intermediate Similarity	NPD7808	Phase 3
0.7333	Intermediate Similarity	NPD4965	Approved
0.7333	Intermediate Similarity	NPD4967	Phase 2
0.7333	Intermediate Similarity	NPD4966	Approved
0.7326	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7325	Intermediate Similarity	NPD7003	Approved
0.7308	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD4060	Phase 1
0.7299	Intermediate Similarity	NPD8312	Approved
0.7299	Intermediate Similarity	NPD8313	Approved
0.7297	Intermediate Similarity	NPD1470	Approved
0.7297	Intermediate Similarity	NPD3267	Approved
0.7297	Intermediate Similarity	NPD3266	Approved
0.7297	Intermediate Similarity	NPD1164	Approved
0.7292	Intermediate Similarity	NPD5691	Approved
0.7285	Intermediate Similarity	NPD3764	Approved
0.7284	Intermediate Similarity	NPD7458	Discontinued
0.7267	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD6832	Phase 2
0.7267	Intermediate Similarity	NPD4908	Phase 1
0.7262	Intermediate Similarity	NPD7199	Phase 2
0.7261	Intermediate Similarity	NPD2654	Approved
0.7255	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7248	Intermediate Similarity	NPD2798	Approved
0.7244	Intermediate Similarity	NPD1471	Phase 3
0.7219	Intermediate Similarity	NPD4625	Phase 3
0.7195	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7191	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD2979	Phase 3
0.7181	Intermediate Similarity	NPD2797	Approved
0.7181	Intermediate Similarity	NPD8151	Discontinued
0.7176	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7175	Intermediate Similarity	NPD8150	Discontinued
0.7171	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7171	Intermediate Similarity	NPD1296	Phase 2
0.717	Intermediate Similarity	NPD2309	Approved
0.7169	Intermediate Similarity	NPD4288	Approved
0.7162	Intermediate Similarity	NPD4749	Approved
0.7151	Intermediate Similarity	NPD7228	Approved
0.7143	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD2403	Approved
0.7134	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD1019	Discontinued
0.7127	Intermediate Similarity	NPD4363	Phase 3
0.7127	Intermediate Similarity	NPD4360	Phase 2
0.7115	Intermediate Similarity	NPD7033	Discontinued
0.7099	Intermediate Similarity	NPD6273	Approved
0.7097	Intermediate Similarity	NPD7435	Discontinued
0.7095	Intermediate Similarity	NPD9269	Phase 2
0.7095	Intermediate Similarity	NPD4287	Approved
0.7083	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7076	Intermediate Similarity	NPD3926	Phase 2
0.707	Intermediate Similarity	NPD4477	Approved
0.707	Intermediate Similarity	NPD2438	Suspended
0.707	Intermediate Similarity	NPD4476	Approved
0.7069	Intermediate Similarity	NPD1729	Discontinued
0.7066	Intermediate Similarity	NPD5353	Approved
0.7055	Intermediate Similarity	NPD9268	Approved
0.7055	Intermediate Similarity	NPD1651	Approved
0.7052	Intermediate Similarity	NPD3751	Discontinued
0.7052	Intermediate Similarity	NPD7177	Discontinued
0.7052	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD6780	Approved
0.7027	Intermediate Similarity	NPD6782	Approved
0.7027	Intermediate Similarity	NPD6781	Approved
0.7027	Intermediate Similarity	NPD6778	Approved
0.7027	Intermediate Similarity	NPD6779	Approved
0.7027	Intermediate Similarity	NPD6776	Approved
0.7027	Intermediate Similarity	NPD6777	Approved
0.7025	Intermediate Similarity	NPD6005	Phase 3
0.7025	Intermediate Similarity	NPD6004	Phase 3
0.7025	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD6002	Phase 3
0.7022	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7007	Intermediate Similarity	NPD1778	Approved
0.7006	Intermediate Similarity	NPD4308	Phase 3
0.7	Intermediate Similarity	NPD3225	Approved
0.7	Intermediate Similarity	NPD1876	Approved

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data