NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	224.07
Volume:	215.105
LogP:	1.091
LogD:	1.022
LogS:	-2.19
# Rotatable Bonds:	1
TPSA:	94.06
# H-Bond Aceptor:	5
# H-Bond Donor:	4
# Rings:	2
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.593
Synthetic Accessibility Score:	3.747
Fsp3:	0.273
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:	-5.13
MDCK Permeability:	5.767939001088962e-06
Pgp-inhibitor:	0.001
Pgp-substrate:	0.65
Human Intestinal Absorption (HIA):	0.018
20% Bioavailability (F20%):	0.014
30% Bioavailability (F30%):	0.02

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.021
Plasma Protein Binding (PPB):	93.72220611572266%
Volume Distribution (VD):	0.832
Pgp-substrate:	11.065216064453125%

ADMET: Metabolism

CYP1A2-inhibitor:	0.704
CYP1A2-substrate:	0.334
CYP2C19-inhibitor:	0.02
CYP2C19-substrate:	0.087
CYP2C9-inhibitor:	0.144
CYP2C9-substrate:	0.384
CYP2D6-inhibitor:	0.046
CYP2D6-substrate:	0.181
CYP3A4-inhibitor:	0.025
CYP3A4-substrate:	0.078

ADMET: Excretion

Clearance (CL):	12.662
Half-life (T1/2):	0.875

ADMET: Toxicity

hERG Blockers:	0.004
Human Hepatotoxicity (H-HT):	0.172
Drug-inuced Liver Injury (DILI):	0.916
AMES Toxicity:	0.213
Rat Oral Acute Toxicity:	0.181
Maximum Recommended Daily Dose:	0.442
Skin Sensitization:	0.73
Carcinogencity:	0.434
Eye Corrosion:	0.007
Eye Irritation:	0.612
Respiratory Toxicity:	0.852

Download Data

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

Natural Product: NPC166583

Natural Product ID:	NPC166583
*Common Name:**	Pestaphthalide A
IUPAC Name:	(3S)-5,7-dihydroxy-3-[(1S)-1-hydroxyethyl]-6-methyl-3H-2-benzofuran-1-one
Synonyms:
Standard InCHIKey:	GRSVIXWYIHCOGF-XUOSJQGZSA-N
Standard InCHI:	InChI=1S/C11H12O5/c1-4-7(13)3-6-8(9(4)14)11(15)16-10(6)5(2)12/h3,5,10,12-14H,1-2H3/t5-,10+/m0/s1
SMILES:	C[C@@H]([C@H]1OC(=O)c2c1cc(O)c(c2O)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL506432
PubChem CID:	24850093
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002279] Benzene and substituted derivatives [CHEMONTID:0000176] Benzoic acids and derivatives [CHEMONTID:0001248] Hydroxybenzoic acid 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
NPO32872	pestalotiopsis foedan	Species	Sporocadaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18288805]

☑ 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
NPT20	Organism	Candida albicans	Candida albicans	IZ	=	13.0	mm	PMID[489649]

☑ 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 NPC166583 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	325
0.1-0.2	1418
0.2-0.3	3253
0.3-0.4	7552
0.4-0.5	10745
0.5-0.6	4509
0.6-0.7	6262
0.7-0.8	7211
0.8-0.85	1145
0.85-0.9	224
0.9-0.95	51
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC53362
0.9429	High Similarity	NPC275356
0.9384	High Similarity	NPC179178
0.9231	High Similarity	NPC82913
0.9214	High Similarity	NPC158481
0.9189	High Similarity	NPC240768
0.9189	High Similarity	NPC200773
0.9178	High Similarity	NPC8817
0.9172	High Similarity	NPC83272
0.9167	High Similarity	NPC159721
0.9167	High Similarity	NPC471731
0.9161	High Similarity	NPC37530
0.9122	High Similarity	NPC119929
0.911	High Similarity	NPC470357
0.911	High Similarity	NPC473023
0.9103	High Similarity	NPC151607
0.9103	High Similarity	NPC42540
0.9097	High Similarity	NPC322112
0.9097	High Similarity	NPC471733
0.9091	High Similarity	NPC158472
0.9091	High Similarity	NPC99441
0.9085	High Similarity	NPC117985
0.9085	High Similarity	NPC212693
0.9085	High Similarity	NPC94248
0.9041	High Similarity	NPC75694
0.9028	High Similarity	NPC90411
0.9028	High Similarity	NPC472605
0.9028	High Similarity	NPC472604
0.9021	High Similarity	NPC139634
0.9021	High Similarity	NPC88269
0.9021	High Similarity	NPC247409
0.9021	High Similarity	NPC105456
0.9014	High Similarity	NPC70380
0.9	High Similarity	NPC271681
0.9	High Similarity	NPC153783
0.8993	High Similarity	NPC96501
0.8986	High Similarity	NPC470359
0.898	High Similarity	NPC260946
0.8958	High Similarity	NPC472600
0.8958	High Similarity	NPC187690
0.8958	High Similarity	NPC165172
0.8958	High Similarity	NPC64664
0.8958	High Similarity	NPC472601
0.8951	High Similarity	NPC197666
0.8951	High Similarity	NPC126739
0.8951	High Similarity	NPC191835
0.8944	High Similarity	NPC235115
0.8933	High Similarity	NPC70016
0.8933	High Similarity	NPC215921
0.8919	High Similarity	NPC471734
0.8919	High Similarity	NPC137296
0.8904	High Similarity	NPC51106
0.8897	High Similarity	NPC472603
0.8897	High Similarity	NPC149533
0.8897	High Similarity	NPC244923
0.8896	High Similarity	NPC470358
0.8889	High Similarity	NPC84935
0.8889	High Similarity	NPC473395
0.8889	High Similarity	NPC471819
0.8889	High Similarity	NPC77679
0.8889	High Similarity	NPC190020
0.8889	High Similarity	NPC32360
0.8889	High Similarity	NPC268052
0.8882	High Similarity	NPC79998
0.8882	High Similarity	NPC199926
0.8881	High Similarity	NPC194579
0.8867	High Similarity	NPC469670
0.8867	High Similarity	NPC469619
0.8867	High Similarity	NPC56204
0.8857	High Similarity	NPC219892
0.8857	High Similarity	NPC189823
0.8851	High Similarity	NPC471735
0.8844	High Similarity	NPC210425
0.8844	High Similarity	NPC86373
0.8844	High Similarity	NPC280404
0.8844	High Similarity	NPC277426
0.8831	High Similarity	NPC470339
0.8824	High Similarity	NPC150227
0.8819	High Similarity	NPC478200
0.8819	High Similarity	NPC33144
0.8819	High Similarity	NPC472602
0.8816	High Similarity	NPC281477
0.8811	High Similarity	NPC50455
0.8811	High Similarity	NPC291454
0.8803	High Similarity	NPC474394
0.88	High Similarity	NPC270160
0.88	High Similarity	NPC237440
0.8786	High Similarity	NPC296158
0.8776	High Similarity	NPC472610
0.8776	High Similarity	NPC469542
0.8776	High Similarity	NPC472006
0.8774	High Similarity	NPC470810
0.8774	High Similarity	NPC472055
0.8767	High Similarity	NPC478217
0.8767	High Similarity	NPC53649
0.8767	High Similarity	NPC1704
0.8767	High Similarity	NPC313123
0.8767	High Similarity	NPC67650
0.8767	High Similarity	NPC158634
0.8758	High Similarity	NPC16082
0.8758	High Similarity	NPC82592
0.8758	High Similarity	NPC471456
0.875	High Similarity	NPC135837
0.875	High Similarity	NPC71256
0.875	High Similarity	NPC245058
0.875	High Similarity	NPC273483
0.875	High Similarity	NPC115249
0.8741	High Similarity	NPC278375
0.8725	High Similarity	NPC107625
0.8707	High Similarity	NPC474385
0.8707	High Similarity	NPC314271
0.8701	High Similarity	NPC472050
0.8699	High Similarity	NPC155205
0.8693	High Similarity	NPC137301
0.8693	High Similarity	NPC478231
0.8693	High Similarity	NPC301233
0.8693	High Similarity	NPC192189
0.869	High Similarity	NPC221104
0.869	High Similarity	NPC475974
0.8681	High Similarity	NPC472599
0.8681	High Similarity	NPC156967
0.8679	High Similarity	NPC473094
0.8675	High Similarity	NPC198927
0.8671	High Similarity	NPC175943
0.8671	High Similarity	NPC211592
0.8667	High Similarity	NPC210320
0.8667	High Similarity	NPC476463
0.8667	High Similarity	NPC81835
0.8658	High Similarity	NPC297788
0.8658	High Similarity	NPC257558
0.8658	High Similarity	NPC471689
0.8649	High Similarity	NPC478202
0.8645	High Similarity	NPC472889
0.8645	High Similarity	NPC246466
0.8639	High Similarity	NPC130485
0.8639	High Similarity	NPC472035
0.8639	High Similarity	NPC470842
0.8639	High Similarity	NPC478201
0.8636	High Similarity	NPC170189
0.8636	High Similarity	NPC208173
0.8636	High Similarity	NPC478230
0.8636	High Similarity	NPC99381
0.8636	High Similarity	NPC69043
0.863	High Similarity	NPC474655
0.863	High Similarity	NPC52358
0.8627	High Similarity	NPC76041
0.8627	High Similarity	NPC184284
0.8627	High Similarity	NPC167903
0.8627	High Similarity	NPC175978
0.8627	High Similarity	NPC478224
0.8625	High Similarity	NPC473096
0.8625	High Similarity	NPC473095
0.8621	High Similarity	NPC178467
0.8621	High Similarity	NPC474849
0.8621	High Similarity	NPC149372
0.8621	High Similarity	NPC65837
0.8621	High Similarity	NPC474771
0.8618	High Similarity	NPC472891
0.8618	High Similarity	NPC202595
0.8611	High Similarity	NPC142027
0.8611	High Similarity	NPC182496
0.8611	High Similarity	NPC180905
0.8609	High Similarity	NPC73411
0.8609	High Similarity	NPC215711
0.8609	High Similarity	NPC153417
0.8601	High Similarity	NPC180261
0.8601	High Similarity	NPC48036
0.8601	High Similarity	NPC37299
0.86	High Similarity	NPC225173
0.86	High Similarity	NPC85734
0.86	High Similarity	NPC163846
0.86	High Similarity	NPC268366
0.86	High Similarity	NPC470570
0.86	High Similarity	NPC32058
0.8591	High Similarity	NPC126882
0.8591	High Similarity	NPC244691
0.8591	High Similarity	NPC210966
0.8591	High Similarity	NPC478203
0.8591	High Similarity	NPC27106
0.8591	High Similarity	NPC48762
0.8589	High Similarity	NPC324220
0.8589	High Similarity	NPC312630
0.8581	High Similarity	NPC478027
0.8581	High Similarity	NPC469579
0.8571	High Similarity	NPC17219
0.8571	High Similarity	NPC471695
0.8571	High Similarity	NPC168471
0.8571	High Similarity	NPC470102
0.8553	High Similarity	NPC4423
0.8553	High Similarity	NPC233267
0.8553	High Similarity	NPC77325
0.8553	High Similarity	NPC291049
0.8552	High Similarity	NPC326847
0.8543	High Similarity	NPC14098
0.8543	High Similarity	NPC125801
0.8543	High Similarity	NPC202494
0.8543	High Similarity	NPC472036
0.8542	High Similarity	NPC475645
0.8535	High Similarity	NPC243701
0.8533	High Similarity	NPC316535

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 NPC166583 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	289
0.1-0.2	894
0.2-0.3	1896
0.3-0.4	2649
0.4-0.5	1867
0.5-0.6	1031
0.6-0.7	372
0.7-0.8	138
0.8-0.85	11
0.85-0.9	0
0.9-0.95	3
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9041	High Similarity	NPD2533	Approved
0.9041	High Similarity	NPD2532	Approved
0.9041	High Similarity	NPD2534	Approved
0.8503	High Similarity	NPD970	Clinical (unspecified phase)
0.8345	Intermediate Similarity	NPD230	Phase 1
0.8313	Intermediate Similarity	NPD6232	Discontinued
0.8199	Intermediate Similarity	NPD5710	Approved
0.8199	Intermediate Similarity	NPD5711	Approved
0.8176	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.816	Intermediate Similarity	NPD7473	Discontinued
0.8025	Intermediate Similarity	NPD4380	Phase 2
0.7987	Intermediate Similarity	NPD7819	Suspended
0.7987	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7952	Intermediate Similarity	NPD5844	Phase 1
0.795	Intermediate Similarity	NPD7075	Discontinued
0.7925	Intermediate Similarity	NPD1934	Approved
0.7917	Intermediate Similarity	NPD6559	Discontinued
0.7914	Intermediate Similarity	NPD6959	Discontinued
0.7875	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7843	Intermediate Similarity	NPD2800	Approved
0.7815	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7812	Intermediate Similarity	NPD6801	Discontinued
0.78	Intermediate Similarity	NPD1607	Approved
0.7799	Intermediate Similarity	NPD6599	Discontinued
0.7784	Intermediate Similarity	NPD3818	Discontinued
0.7778	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD3882	Suspended
0.7756	Intermediate Similarity	NPD7390	Discontinued
0.7722	Intermediate Similarity	NPD920	Approved
0.7714	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7712	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7712	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7707	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7702	Intermediate Similarity	NPD37	Approved
0.7697	Intermediate Similarity	NPD1510	Phase 2
0.7688	Intermediate Similarity	NPD8150	Discontinued
0.7683	Intermediate Similarity	NPD6234	Discontinued
0.7677	Intermediate Similarity	NPD4628	Phase 3
0.7669	Intermediate Similarity	NPD4966	Approved
0.7669	Intermediate Similarity	NPD4967	Phase 2
0.7669	Intermediate Similarity	NPD4965	Approved
0.7667	Intermediate Similarity	NPD943	Approved
0.7667	Intermediate Similarity	NPD1240	Approved
0.7662	Intermediate Similarity	NPD1549	Phase 2
0.7654	Intermediate Similarity	NPD2801	Approved
0.7654	Intermediate Similarity	NPD1465	Phase 2
0.7647	Intermediate Similarity	NPD2935	Discontinued
0.7647	Intermediate Similarity	NPD1551	Phase 2
0.7643	Intermediate Similarity	NPD6799	Approved
0.7643	Intermediate Similarity	NPD1511	Approved
0.7636	Intermediate Similarity	NPD5494	Approved
0.7625	Intermediate Similarity	NPD3226	Approved
0.7622	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7622	Intermediate Similarity	NPD3749	Approved
0.7613	Intermediate Similarity	NPD1243	Approved
0.7607	Intermediate Similarity	NPD3817	Phase 2
0.7606	Intermediate Similarity	NPD9545	Approved
0.7595	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7586	Intermediate Similarity	NPD9269	Phase 2
0.7576	Intermediate Similarity	NPD919	Approved
0.7564	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.756	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.756	Intermediate Similarity	NPD6166	Phase 2
0.756	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7547	Intermediate Similarity	NPD1512	Approved
0.7533	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7533	Intermediate Similarity	NPD3764	Approved
0.7532	Intermediate Similarity	NPD5408	Approved
0.7532	Intermediate Similarity	NPD5404	Approved
0.7532	Intermediate Similarity	NPD5405	Approved
0.7532	Intermediate Similarity	NPD5406	Approved
0.7531	Intermediate Similarity	NPD7411	Suspended
0.7529	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD5402	Approved
0.75	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD7074	Phase 3
0.7484	Intermediate Similarity	NPD2346	Discontinued
0.7471	Intermediate Similarity	NPD7228	Approved
0.7468	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7465	Intermediate Similarity	NPD9493	Approved
0.7457	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7455	Intermediate Similarity	NPD7768	Phase 2
0.7452	Intermediate Similarity	NPD3750	Approved
0.7431	Intermediate Similarity	NPD9268	Approved
0.7427	Intermediate Similarity	NPD7054	Approved
0.7414	Intermediate Similarity	NPD8313	Approved
0.7414	Intermediate Similarity	NPD8312	Approved
0.7401	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD447	Suspended
0.7384	Intermediate Similarity	NPD7472	Approved
0.7381	Intermediate Similarity	NPD1247	Approved
0.738	Intermediate Similarity	NPD8151	Discontinued
0.7375	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7353	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7342	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7341	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7341	Intermediate Similarity	NPD6797	Phase 2
0.7333	Intermediate Similarity	NPD6534	Approved
0.7333	Intermediate Similarity	NPD6535	Approved
0.7315	Intermediate Similarity	NPD1470	Approved
0.7308	Intermediate Similarity	NPD2796	Approved
0.7299	Intermediate Similarity	NPD7251	Discontinued
0.7297	Intermediate Similarity	NPD7435	Discontinued
0.7296	Intermediate Similarity	NPD6190	Approved
0.7284	Intermediate Similarity	NPD5403	Approved
0.7279	Intermediate Similarity	NPD1201	Approved
0.7278	Intermediate Similarity	NPD7199	Phase 2
0.7267	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD5401	Approved
0.7258	Intermediate Similarity	NPD8320	Phase 1
0.7258	Intermediate Similarity	NPD8319	Approved
0.7257	Intermediate Similarity	NPD7808	Phase 3
0.7235	Intermediate Similarity	NPD7229	Phase 3
0.7228	Intermediate Similarity	NPD6779	Approved
0.7228	Intermediate Similarity	NPD6776	Approved
0.7228	Intermediate Similarity	NPD6778	Approved
0.7228	Intermediate Similarity	NPD6782	Approved
0.7228	Intermediate Similarity	NPD6781	Approved
0.7228	Intermediate Similarity	NPD6780	Approved
0.7228	Intermediate Similarity	NPD6777	Approved
0.7226	Intermediate Similarity	NPD6651	Approved
0.7213	Intermediate Similarity	NPD7700	Phase 2
0.7213	Intermediate Similarity	NPD7699	Phase 2
0.72	Intermediate Similarity	NPD1164	Approved
0.7195	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7191	Intermediate Similarity	NPD8434	Phase 2
0.719	Intermediate Similarity	NPD411	Approved
0.719	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD5953	Discontinued
0.7143	Intermediate Similarity	NPD4626	Approved
0.7135	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD3748	Approved
0.7134	Intermediate Similarity	NPD2799	Discontinued
0.7133	Intermediate Similarity	NPD1283	Approved
0.7126	Intermediate Similarity	NPD7286	Phase 2
0.712	Intermediate Similarity	NPD7783	Phase 2
0.712	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7114	Intermediate Similarity	NPD9717	Approved
0.7102	Intermediate Similarity	NPD7240	Approved
0.7093	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD6100	Approved
0.7089	Intermediate Similarity	NPD6099	Approved
0.7088	Intermediate Similarity	NPD6213	Phase 3
0.7088	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.7088	Intermediate Similarity	NPD6212	Phase 3
0.7075	Intermediate Similarity	NPD5691	Approved
0.7073	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7069	Intermediate Similarity	NPD3751	Discontinued
0.7068	Intermediate Similarity	NPD7874	Approved
0.7068	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7062	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7044	Intermediate Similarity	NPD6002	Phase 3
0.7044	Intermediate Similarity	NPD2344	Approved
0.7044	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7044	Intermediate Similarity	NPD6004	Phase 3
0.7044	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7044	Intermediate Similarity	NPD6005	Phase 3
0.7021	Intermediate Similarity	NPD7697	Approved
0.7021	Intermediate Similarity	NPD7698	Approved
0.7021	Intermediate Similarity	NPD7696	Phase 3
0.7013	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD3926	Phase 2
0.6993	Remote Similarity	NPD9494	Approved
0.6988	Remote Similarity	NPD7458	Discontinued
0.6987	Remote Similarity	NPD4060	Phase 1
0.6987	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6987	Remote Similarity	NPD1613	Approved
0.6986	Remote Similarity	NPD405	Clinical (unspecified phase)
0.6984	Remote Similarity	NPD7870	Phase 2
0.6984	Remote Similarity	NPD7871	Phase 2
0.6981	Remote Similarity	NPD2438	Suspended
0.6974	Remote Similarity	NPD1203	Approved
0.6968	Remote Similarity	NPD2313	Discontinued
0.6968	Remote Similarity	NPD6823	Phase 2
0.6963	Remote Similarity	NPD7701	Phase 2
0.6957	Remote Similarity	NPD2654	Approved
0.6936	Remote Similarity	NPD3787	Discontinued
0.6933	Remote Similarity	NPD1281	Approved
0.6933	Remote Similarity	NPD422	Phase 1
0.6918	Remote Similarity	NPD7033	Discontinued
0.6914	Remote Similarity	NPD7003	Approved
0.6909	Remote Similarity	NPD6273	Approved
0.6903	Remote Similarity	NPD3027	Phase 3
0.6901	Remote Similarity	NPD9266	Approved
0.6901	Remote Similarity	NPD74	Approved
0.6887	Remote Similarity	NPD1608	Approved
0.6882	Remote Similarity	NPD8090	Clinical (unspecified phase)
0.6882	Remote Similarity	NPD5353	Approved
0.6879	Remote Similarity	NPD2979	Phase 3
0.6875	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6871	Remote Similarity	NPD2309	Approved
0.6856	Remote Similarity	NPD7801	Approved
0.6852	Remote Similarity	NPD1652	Phase 2
0.6837	Remote Similarity	NPD7930	Approved
0.6835	Remote Similarity	NPD5124	Phase 1
0.6835	Remote Similarity	NPD6355	Discontinued
0.6835	Remote Similarity	NPD1899	Clinical (unspecified phase)

Bioactivity similarity: Similar Natural Products in NPASS

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

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

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data