NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	236.07
Volume:	229.764
LogP:	0.963
LogD:	1.223
LogS:	-2.706
# Rotatable Bonds:	1
TPSA:	90.9
# H-Bond Aceptor:	5
# H-Bond Donor:	3
# Rings:	2
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.694
Synthetic Accessibility Score:	2.951
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:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.903
MDCK Permeability:	4.604598871082999e-06
Pgp-inhibitor:	0.001
Pgp-substrate:	0.906
Human Intestinal Absorption (HIA):	0.019
20% Bioavailability (F20%):	0.023
30% Bioavailability (F30%):	0.108

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.014
Plasma Protein Binding (PPB):	92.18350219726562%
Volume Distribution (VD):	0.609
Pgp-substrate:	7.876983165740967%

ADMET: Metabolism

CYP1A2-inhibitor:	0.952
CYP1A2-substrate:	0.852
CYP2C19-inhibitor:	0.044
CYP2C19-substrate:	0.08
CYP2C9-inhibitor:	0.189
CYP2C9-substrate:	0.774
CYP2D6-inhibitor:	0.14
CYP2D6-substrate:	0.272
CYP3A4-inhibitor:	0.099
CYP3A4-substrate:	0.141

ADMET: Excretion

Clearance (CL):	6.058
Half-life (T1/2):	0.875

ADMET: Toxicity

hERG Blockers:	0.005
Human Hepatotoxicity (H-HT):	0.865
Drug-inuced Liver Injury (DILI):	0.978
AMES Toxicity:	0.475
Rat Oral Acute Toxicity:	0.06
Maximum Recommended Daily Dose:	0.208
Skin Sensitization:	0.827
Carcinogencity:	0.059
Eye Corrosion:	0.133
Eye Irritation:	0.95
Respiratory Toxicity:	0.129

Download Data

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

Natural Product: NPC82913

Natural Product ID:	NPC82913
*Common Name:**	Decarboxyhydroxycitrinone
IUPAC Name:	6,8-dihydroxy-3-(hydroxymethyl)-4,5-dimethylisochromen-1-one
Synonyms:	Decarboxyhydroxycitrinone
Standard InCHIKey:	CBRPTHQFXQJGOV-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C12H12O5/c1-5-7(14)3-8(15)11-10(5)6(2)9(4-13)17-12(11)16/h3,13-15H,4H2,1-2H3
SMILES:	OCc1oc(=O)c2c(c1C)c(C)c(cc2O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1812033
PubChem CID:	53388140
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0001890] Isocoumarins and derivatives

*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
NPO19108	Arthrinium sacchari	Species	Apiosporaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21718054]
NPO19108	Arthrinium sacchari	Species	Apiosporaceae	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
IC50	2

Activity Type	# Activity
Cell Line	1
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT737	Cell Line	HUVEC	Homo sapiens	IC50	=	7600.0	nM	PMID[485696]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	17400.0	nM	PMID[485696]

☑ 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 NPC82913 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	386
0.1-0.2	1805
0.2-0.3	4455
0.3-0.4	9893
0.4-0.5	8308
0.5-0.6	3997
0.6-0.7	5697
0.7-0.8	4830
0.8-0.85	2816
0.85-0.9	475
0.9-0.95	32
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9632	High Similarity	NPC247409
0.9556	High Similarity	NPC50455
0.9424	High Similarity	NPC322112
0.9353	High Similarity	NPC472605
0.9353	High Similarity	NPC472604
0.9348	High Similarity	NPC268052
0.9348	High Similarity	NPC32360
0.9348	High Similarity	NPC88269
0.9296	High Similarity	NPC473023
0.9296	High Similarity	NPC260946
0.9281	High Similarity	NPC472600
0.9281	High Similarity	NPC472601
0.9265	High Similarity	NPC175943
0.9231	High Similarity	NPC166583
0.9231	High Similarity	NPC53362
0.9214	High Similarity	NPC158634
0.9214	High Similarity	NPC472603
0.9209	High Similarity	NPC275356
0.9191	High Similarity	NPC153783
0.9172	High Similarity	NPC179178
0.9143	High Similarity	NPC64664
0.9143	High Similarity	NPC158472
0.9137	High Similarity	NPC94248
0.9137	High Similarity	NPC212693
0.913	High Similarity	NPC158481
0.913	High Similarity	NPC235115
0.9091	High Similarity	NPC473692
0.9085	High Similarity	NPC159721
0.9085	High Similarity	NPC472610
0.9085	High Similarity	NPC469542
0.9085	High Similarity	NPC471731
0.9078	High Similarity	NPC37530
0.9071	High Similarity	NPC105456
0.9071	High Similarity	NPC139634
0.9071	High Similarity	NPC92655
0.9065	High Similarity	NPC194579
0.9065	High Similarity	NPC135837
0.9065	High Similarity	NPC70380
0.9044	High Similarity	NPC189823
0.9044	High Similarity	NPC219892
0.9021	High Similarity	NPC151607
0.9021	High Similarity	NPC210425
0.9021	High Similarity	NPC277426
0.9021	High Similarity	NPC86373
0.9021	High Similarity	NPC280404
0.9021	High Similarity	NPC42540
0.9014	High Similarity	NPC471733
0.9007	High Similarity	NPC99441
0.9007	High Similarity	NPC165172
0.9	High Similarity	NPC472602
0.9	High Similarity	NPC191835
0.9	High Similarity	NPC221104
0.8993	High Similarity	NPC291454
0.8986	High Similarity	NPC192189
0.898	High Similarity	NPC215921
0.898	High Similarity	NPC70016
0.8973	High Similarity	NPC270160
0.8973	High Similarity	NPC237440
0.8958	High Similarity	NPC83272
0.8951	High Similarity	NPC478202
0.8951	High Similarity	NPC51106
0.8944	High Similarity	NPC67650
0.8944	High Similarity	NPC1704
0.8944	High Similarity	NPC53649
0.8921	High Similarity	NPC182496
0.8921	High Similarity	NPC180905
0.8919	High Similarity	NPC115249
0.8919	High Similarity	NPC478224
0.8912	High Similarity	NPC472891
0.8881	High Similarity	NPC469579
0.8881	High Similarity	NPC474385
0.8873	High Similarity	NPC471697
0.8873	High Similarity	NPC155205
0.8865	High Similarity	NPC33144
0.8865	High Similarity	NPC126739
0.8865	High Similarity	NPC478200
0.8865	High Similarity	NPC197666
0.8859	High Similarity	NPC137301
0.8859	High Similarity	NPC281477
0.8851	High Similarity	NPC240768
0.8851	High Similarity	NPC200773
0.8836	High Similarity	NPC210320
0.8836	High Similarity	NPC471734
0.8832	High Similarity	NPC296158
0.8819	High Similarity	NPC472006
0.8811	High Similarity	NPC478217
0.8811	High Similarity	NPC90411
0.8811	High Similarity	NPC313123
0.8811	High Similarity	NPC470842
0.8811	High Similarity	NPC149533
0.8811	High Similarity	NPC244923
0.8808	High Similarity	NPC246466
0.8808	High Similarity	NPC472889
0.8803	High Similarity	NPC52358
0.8803	High Similarity	NPC471819
0.88	High Similarity	NPC478230
0.88	High Similarity	NPC82592
0.88	High Similarity	NPC208173
0.88	High Similarity	NPC69043
0.88	High Similarity	NPC16082
0.88	High Similarity	NPC170189
0.8794	High Similarity	NPC71256
0.8794	High Similarity	NPC245058
0.8792	High Similarity	NPC167903
0.8792	High Similarity	NPC273483
0.8792	High Similarity	NPC184284
0.8792	High Similarity	NPC76041
0.8792	High Similarity	NPC271681
0.8786	High Similarity	NPC142027
0.8784	High Similarity	NPC119929
0.8784	High Similarity	NPC469619
0.8784	High Similarity	NPC469670
0.8776	High Similarity	NPC37139
0.8776	High Similarity	NPC215711
0.8776	High Similarity	NPC240253
0.8776	High Similarity	NPC73411
0.8776	High Similarity	NPC153417
0.8776	High Similarity	NPC240622
0.8776	High Similarity	NPC471642
0.8776	High Similarity	NPC471641
0.8767	High Similarity	NPC138978
0.8767	High Similarity	NPC225173
0.8767	High Similarity	NPC163846
0.8767	High Similarity	NPC471735
0.8759	High Similarity	NPC257025
0.8758	High Similarity	NPC117985
0.875	High Similarity	NPC250755
0.875	High Similarity	NPC470339
0.875	High Similarity	NPC314271
0.8742	High Similarity	NPC472050
0.8741	High Similarity	NPC156872
0.8741	High Similarity	NPC187690
0.8733	High Similarity	NPC471695
0.8733	High Similarity	NPC478231
0.8732	High Similarity	NPC475974
0.8725	High Similarity	NPC204350
0.8723	High Similarity	NPC472599
0.8723	High Similarity	NPC156967
0.8716	High Similarity	NPC233267
0.8716	High Similarity	NPC4423
0.8716	High Similarity	NPC77325
0.8716	High Similarity	NPC291049
0.8714	High Similarity	NPC475645
0.8707	High Similarity	NPC125801
0.8707	High Similarity	NPC476463
0.8699	High Similarity	NPC134621
0.8699	High Similarity	NPC312789
0.8699	High Similarity	NPC297788
0.8693	High Similarity	NPC472055
0.8684	High Similarity	NPC77679
0.8684	High Similarity	NPC190020
0.8684	High Similarity	NPC84935
0.8681	High Similarity	NPC478201
0.8681	High Similarity	NPC220106
0.8681	High Similarity	NPC130485
0.8681	High Similarity	NPC475730
0.8681	High Similarity	NPC472035
0.8675	High Similarity	NPC199926
0.8675	High Similarity	NPC16286
0.8675	High Similarity	NPC317585
0.8675	High Similarity	NPC472890
0.8675	High Similarity	NPC478221
0.8671	High Similarity	NPC474655
0.8667	High Similarity	NPC175978
0.8667	High Similarity	NPC256141
0.8662	High Similarity	NPC178467
0.8662	High Similarity	NPC149372
0.8662	High Similarity	NPC301915
0.8662	High Similarity	NPC474849
0.8662	High Similarity	NPC65837
0.8662	High Similarity	NPC261292
0.8662	High Similarity	NPC474771
0.8658	High Similarity	NPC158866
0.8658	High Similarity	NPC56204
0.8658	High Similarity	NPC96501
0.8652	High Similarity	NPC27407
0.8652	High Similarity	NPC278375
0.8649	High Similarity	NPC105415
0.8649	High Similarity	NPC221352
0.8643	High Similarity	NPC470988
0.8639	High Similarity	NPC267509
0.8639	High Similarity	NPC237208
0.8639	High Similarity	NPC268366
0.8639	High Similarity	NPC107625
0.8633	High Similarity	NPC470831
0.8633	High Similarity	NPC214702
0.863	High Similarity	NPC66404
0.863	High Similarity	NPC255133
0.863	High Similarity	NPC95123
0.863	High Similarity	NPC242100
0.8621	High Similarity	NPC105648
0.8621	High Similarity	NPC94076
0.8621	High Similarity	NPC182255
0.8618	High Similarity	NPC197751
0.8618	High Similarity	NPC150227
0.8618	High Similarity	NPC227062
0.8611	High Similarity	NPC168471
0.8609	High Similarity	NPC472799
0.8603	High Similarity	NPC262671
0.8603	High Similarity	NPC201728

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 NPC82913 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	372
0.1-0.2	1021
0.2-0.3	2027
0.3-0.4	2553
0.4-0.5	1743
0.5-0.6	927
0.6-0.7	340
0.7-0.8	115
0.8-0.85	44
0.85-0.9	7
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9071	High Similarity	NPD970	Clinical (unspecified phase)
0.8571	High Similarity	NPD2532	Approved
0.8571	High Similarity	NPD2534	Approved
0.8571	High Similarity	NPD2533	Approved
0.8366	Intermediate Similarity	NPD7819	Suspended
0.8301	Intermediate Similarity	NPD6801	Discontinued
0.8289	Intermediate Similarity	NPD4380	Phase 2
0.8252	Intermediate Similarity	NPD230	Phase 1
0.8228	Intermediate Similarity	NPD6232	Discontinued
0.8207	Intermediate Similarity	NPD1510	Phase 2
0.8205	Intermediate Similarity	NPD7075	Discontinued
0.8129	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8129	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8082	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.8079	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8075	Intermediate Similarity	NPD7473	Discontinued
0.8065	Intermediate Similarity	NPD1934	Approved
0.8056	Intermediate Similarity	NPD1240	Approved
0.8013	Intermediate Similarity	NPD1511	Approved
0.8013	Intermediate Similarity	NPD6799	Approved
0.7973	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7973	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7962	Intermediate Similarity	NPD3817	Phase 2
0.7945	Intermediate Similarity	NPD1607	Approved
0.7937	Intermediate Similarity	NPD6959	Discontinued
0.7935	Intermediate Similarity	NPD6599	Discontinued
0.7933	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7933	Intermediate Similarity	NPD3750	Approved
0.7919	Intermediate Similarity	NPD1549	Phase 2
0.7908	Intermediate Similarity	NPD1512	Approved
0.7905	Intermediate Similarity	NPD2935	Discontinued
0.7898	Intermediate Similarity	NPD1465	Phase 2
0.7898	Intermediate Similarity	NPD2801	Approved
0.7888	Intermediate Similarity	NPD5710	Approved
0.7888	Intermediate Similarity	NPD5711	Approved
0.7885	Intermediate Similarity	NPD7411	Suspended
0.7867	Intermediate Similarity	NPD2800	Approved
0.7867	Intermediate Similarity	NPD1243	Approved
0.7866	Intermediate Similarity	NPD5844	Phase 1
0.7862	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7857	Intermediate Similarity	NPD920	Approved
0.7812	Intermediate Similarity	NPD919	Approved
0.7808	Intermediate Similarity	NPD943	Approved
0.7799	Intermediate Similarity	NPD3882	Suspended
0.7799	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7799	Intermediate Similarity	NPD7768	Phase 2
0.7785	Intermediate Similarity	NPD1551	Phase 2
0.7758	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7754	Intermediate Similarity	NPD9545	Approved
0.7736	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7727	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7718	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7712	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7703	Intermediate Similarity	NPD6651	Approved
0.7697	Intermediate Similarity	NPD3818	Discontinued
0.7697	Intermediate Similarity	NPD4628	Phase 3
0.7683	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7683	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7683	Intermediate Similarity	NPD6166	Phase 2
0.7683	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7667	Intermediate Similarity	NPD2796	Approved
0.7662	Intermediate Similarity	NPD7390	Discontinued
0.7651	Intermediate Similarity	NPD7054	Approved
0.764	Intermediate Similarity	NPD3749	Approved
0.7628	Intermediate Similarity	NPD5403	Approved
0.7625	Intermediate Similarity	NPD5402	Approved
0.7619	Intermediate Similarity	NPD6559	Discontinued
0.7613	Intermediate Similarity	NPD5401	Approved
0.7613	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7609	Intermediate Similarity	NPD9493	Approved
0.7605	Intermediate Similarity	NPD7472	Approved
0.7605	Intermediate Similarity	NPD7074	Phase 3
0.76	Intermediate Similarity	NPD3748	Approved
0.7574	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.756	Intermediate Similarity	NPD6797	Phase 2
0.7551	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.755	Intermediate Similarity	NPD5406	Approved
0.755	Intermediate Similarity	NPD5408	Approved
0.755	Intermediate Similarity	NPD5404	Approved
0.755	Intermediate Similarity	NPD5405	Approved
0.7532	Intermediate Similarity	NPD3226	Approved
0.7529	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7515	Intermediate Similarity	NPD7251	Discontinued
0.7483	Intermediate Similarity	NPD9269	Phase 2
0.7471	Intermediate Similarity	NPD7808	Phase 3
0.7468	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7448	Intermediate Similarity	NPD1164	Approved
0.7439	Intermediate Similarity	NPD5494	Approved
0.7432	Intermediate Similarity	NPD3764	Approved
0.7413	Intermediate Similarity	NPD422	Phase 1
0.7413	Intermediate Similarity	NPD1201	Approved
0.74	Intermediate Similarity	NPD447	Suspended
0.7399	Intermediate Similarity	NPD8150	Discontinued
0.7394	Intermediate Similarity	NPD1247	Approved
0.7394	Intermediate Similarity	NPD7199	Phase 2
0.7391	Intermediate Similarity	NPD37	Approved
0.7386	Intermediate Similarity	NPD2346	Discontinued
0.7378	Intermediate Similarity	NPD6234	Discontinued
0.7368	Intermediate Similarity	NPD2799	Discontinued
0.7362	Intermediate Similarity	NPD4966	Approved
0.7362	Intermediate Similarity	NPD4965	Approved
0.7362	Intermediate Similarity	NPD4967	Phase 2
0.7361	Intermediate Similarity	NPD9717	Approved
0.7353	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7353	Intermediate Similarity	NPD5953	Discontinued
0.7337	Intermediate Similarity	NPD7286	Phase 2
0.7333	Intermediate Similarity	NPD4060	Phase 1
0.7329	Intermediate Similarity	NPD1203	Approved
0.7329	Intermediate Similarity	NPD1470	Approved
0.7324	Intermediate Similarity	NPD9268	Approved
0.7267	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.726	Intermediate Similarity	NPD1283	Approved
0.7241	Intermediate Similarity	NPD1608	Approved
0.7225	Intermediate Similarity	NPD8312	Approved
0.7225	Intermediate Similarity	NPD8313	Approved
0.7216	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7208	Intermediate Similarity	NPD6100	Approved
0.7208	Intermediate Similarity	NPD6099	Approved
0.7205	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7204	Intermediate Similarity	NPD8151	Discontinued
0.7202	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD411	Approved
0.72	Intermediate Similarity	NPD2313	Discontinued
0.7197	Intermediate Similarity	NPD6190	Approved
0.7188	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD7228	Approved
0.7171	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7171	Intermediate Similarity	NPD5124	Phase 1
0.717	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7167	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7153	Intermediate Similarity	NPD4626	Approved
0.7143	Intermediate Similarity	NPD7033	Discontinued
0.7143	Intermediate Similarity	NPD7229	Phase 3
0.712	Intermediate Similarity	NPD7435	Discontinued
0.7114	Intermediate Similarity	NPD9494	Approved
0.7113	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD1613	Approved
0.7099	Intermediate Similarity	NPD7458	Discontinued
0.7091	Intermediate Similarity	NPD4288	Approved
0.7086	Intermediate Similarity	NPD1296	Phase 2
0.7083	Intermediate Similarity	NPD5691	Approved
0.7076	Intermediate Similarity	NPD3751	Discontinued
0.707	Intermediate Similarity	NPD1652	Phase 2
0.7067	Intermediate Similarity	NPD6832	Phase 2
0.7063	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7056	Intermediate Similarity	NPD6534	Approved
0.7056	Intermediate Similarity	NPD6535	Approved
0.7055	Intermediate Similarity	NPD1281	Approved
0.7051	Intermediate Similarity	NPD2344	Approved
0.7049	Intermediate Similarity	NPD6777	Approved
0.7049	Intermediate Similarity	NPD6780	Approved
0.7049	Intermediate Similarity	NPD6778	Approved
0.7049	Intermediate Similarity	NPD6781	Approved
0.7049	Intermediate Similarity	NPD6782	Approved
0.7049	Intermediate Similarity	NPD6779	Approved
0.7049	Intermediate Similarity	NPD6776	Approved
0.7037	Intermediate Similarity	NPD1653	Approved
0.7034	Intermediate Similarity	NPD17	Approved
0.7029	Intermediate Similarity	NPD9266	Approved
0.7029	Intermediate Similarity	NPD74	Approved
0.7025	Intermediate Similarity	NPD7003	Approved
0.702	Intermediate Similarity	NPD3027	Phase 3
0.7	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD3926	Phase 2
0.6989	Remote Similarity	NPD8320	Phase 1
0.6989	Remote Similarity	NPD8319	Approved
0.6987	Remote Similarity	NPD2438	Suspended
0.698	Remote Similarity	NPD2797	Approved
0.6974	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6974	Remote Similarity	NPD3268	Approved
0.6962	Remote Similarity	NPD2654	Approved
0.6957	Remote Similarity	NPD9264	Approved
0.6957	Remote Similarity	NPD9263	Approved
0.6957	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD9267	Approved
0.6954	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6948	Remote Similarity	NPD6355	Discontinued
0.6947	Remote Similarity	NPD7783	Phase 2
0.6947	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6941	Remote Similarity	NPD3787	Discontinued
0.694	Remote Similarity	NPD7699	Phase 2
0.694	Remote Similarity	NPD7700	Phase 2
0.6939	Remote Similarity	NPD1610	Phase 2
0.6933	Remote Similarity	NPD2798	Approved
0.6933	Remote Similarity	NPD1019	Discontinued
0.6933	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD4308	Phase 3
0.6918	Remote Similarity	NPD8166	Discontinued
0.6914	Remote Similarity	NPD6273	Approved
0.691	Remote Similarity	NPD8434	Phase 2
0.6908	Remote Similarity	NPD4625	Phase 3
0.6901	Remote Similarity	NPD5242	Approved
0.6897	Remote Similarity	NPD1548	Phase 1
0.6895	Remote Similarity	NPD7874	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