NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	260.14
Volume:	281.368
LogP:	4.25
LogD:	3.496
LogS:	-3.687
# Rotatable Bonds:	2
TPSA:	46.53
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.826
Synthetic Accessibility Score:	2.913
Fsp3:	0.438
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.62
MDCK Permeability:	2.226730612164829e-05
Pgp-inhibitor:	0.062
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.012
20% Bioavailability (F20%):	0.887
30% Bioavailability (F30%):	0.009

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.334
Plasma Protein Binding (PPB):	95.54143524169922%
Volume Distribution (VD):	1.457
Pgp-substrate:	4.719759941101074%

ADMET: Metabolism

CYP1A2-inhibitor:	0.924
CYP1A2-substrate:	0.385
CYP2C19-inhibitor:	0.891
CYP2C19-substrate:	0.417
CYP2C9-inhibitor:	0.619
CYP2C9-substrate:	0.921
CYP2D6-inhibitor:	0.679
CYP2D6-substrate:	0.461
CYP3A4-inhibitor:	0.183
CYP3A4-substrate:	0.167

ADMET: Excretion

Clearance (CL):	15.362
Half-life (T1/2):	0.298

ADMET: Toxicity

hERG Blockers:	0.019
Human Hepatotoxicity (H-HT):	0.617
Drug-inuced Liver Injury (DILI):	0.118
AMES Toxicity:	0.012
Rat Oral Acute Toxicity:	0.209
Maximum Recommended Daily Dose:	0.278
Skin Sensitization:	0.288
Carcinogencity:	0.413
Eye Corrosion:	0.003
Eye Irritation:	0.052
Respiratory Toxicity:	0.193

Download Data

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

Natural Product: NPC118253

Natural Product ID:	NPC118253
*Common Name:**	Pestaloficiol J
IUPAC Name:	6-hydroxy-2,2-dimethyl-8-(3-methylbut-2-enyl)-3H-chromen-4-one
Synonyms:	Pestaloficiol J
Standard InCHIKey:	MQRXYQNCQPECMC-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C16H20O3/c1-10(2)5-6-11-7-12(17)8-13-14(18)9-16(3,4)19-15(11)13/h5,7-8,17H,6,9H2,1-4H3
SMILES:	CC(=CCc1cc(O)cc2c1OC(C)(C)CC2=O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1080258
PubChem CID:	44254252
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000123] Benzopyrans [CHEMONTID:0003410] 1-benzopyrans [CHEMONTID:0003522] 2,2-dimethyl-1-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
NPO22690	Pestalotiopsis fici	Species	Sporocadaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18468908]
NPO22690	Pestalotiopsis fici	Species	Sporocadaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19101157]
NPO22690	Pestalotiopsis fici	Species	Sporocadaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19618920]
NPO22690	Pestalotiopsis fici	Species	Sporocadaceae	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
EC50	2
IC50	2

Activity Type	# Activity
Cell Line	3
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT165	Cell Line	HeLa	Homo sapiens	IC50	=	21200.0	nM	PMID[559978]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	>	153800.0	nM	PMID[559978]
NPT1452	Cell Line	C8166	Homo sapiens	EC50	>	100000.0	nM	PMID[559978]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	EC50	=	8000.0	nM	PMID[559978]

☑ 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 NPC118253 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	354
0.1-0.2	1647
0.2-0.3	4432
0.3-0.4	11257
0.4-0.5	6957
0.5-0.6	4508
0.6-0.7	7272
0.7-0.8	5901
0.8-0.85	320
0.85-0.9	42
0.9-0.95	6
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9225	High Similarity	NPC278787
0.9154	High Similarity	NPC141549
0.9134	High Similarity	NPC224657
0.9077	High Similarity	NPC7569
0.8931	High Similarity	NPC196621
0.8881	High Similarity	NPC22222
0.8881	High Similarity	NPC281513
0.8841	High Similarity	NPC329493
0.876	High Similarity	NPC147896
0.8732	High Similarity	NPC37135
0.8732	High Similarity	NPC186397
0.8712	High Similarity	NPC473019
0.8702	High Similarity	NPC298884
0.8676	High Similarity	NPC278832
0.8676	High Similarity	NPC64157
0.8676	High Similarity	NPC472881
0.8671	High Similarity	NPC223988
0.8671	High Similarity	NPC266499
0.8633	High Similarity	NPC145673
0.8623	High Similarity	NPC18457
0.8615	High Similarity	NPC4012
0.8615	High Similarity	NPC276962
0.8615	High Similarity	NPC190086
0.8611	High Similarity	NPC120105
0.8611	High Similarity	NPC101957
0.8605	High Similarity	NPC49441
0.8592	High Similarity	NPC211565
0.8582	High Similarity	NPC474246
0.8582	High Similarity	NPC474143
0.8571	High Similarity	NPC269414
0.8571	High Similarity	NPC271832
0.8571	High Similarity	NPC59654
0.8561	High Similarity	NPC95034
0.8561	High Similarity	NPC142087
0.8551	High Similarity	NPC98395
0.8529	High Similarity	NPC477210
0.8529	High Similarity	NPC265793
0.85	High Similarity	NPC124365
0.8492	Intermediate Similarity	NPC69539
0.8489	Intermediate Similarity	NPC470671
0.8489	Intermediate Similarity	NPC473988
0.8489	Intermediate Similarity	NPC470672
0.8489	Intermediate Similarity	NPC474487
0.8489	Intermediate Similarity	NPC474504
0.8485	Intermediate Similarity	NPC237868
0.8483	Intermediate Similarity	NPC227122
0.8478	Intermediate Similarity	NPC130976
0.8478	Intermediate Similarity	NPC477534
0.8473	Intermediate Similarity	NPC474237
0.8462	Intermediate Similarity	NPC60389
0.8451	Intermediate Similarity	NPC274085
0.8451	Intermediate Similarity	NPC89664
0.8435	Intermediate Similarity	NPC178964
0.8435	Intermediate Similarity	NPC95842
0.8435	Intermediate Similarity	NPC280530
0.8425	Intermediate Similarity	NPC187993
0.8425	Intermediate Similarity	NPC238176
0.8421	Intermediate Similarity	NPC71525
0.8413	Intermediate Similarity	NPC240163
0.8389	Intermediate Similarity	NPC196448
0.8382	Intermediate Similarity	NPC251549
0.838	Intermediate Similarity	NPC159855
0.838	Intermediate Similarity	NPC144499
0.838	Intermediate Similarity	NPC169479
0.838	Intermediate Similarity	NPC316691
0.8378	Intermediate Similarity	NPC113906
0.837	Intermediate Similarity	NPC475880
0.8369	Intermediate Similarity	NPC477272
0.8358	Intermediate Similarity	NPC201419
0.8357	Intermediate Similarity	NPC131130
0.8346	Intermediate Similarity	NPC306765
0.8333	Intermediate Similarity	NPC24136
0.8333	Intermediate Similarity	NPC193805
0.8333	Intermediate Similarity	NPC308799
0.8333	Intermediate Similarity	NPC290133
0.8333	Intermediate Similarity	NPC187282
0.8322	Intermediate Similarity	NPC18585
0.8322	Intermediate Similarity	NPC471600
0.8322	Intermediate Similarity	NPC106985
0.8322	Intermediate Similarity	NPC166138
0.8322	Intermediate Similarity	NPC138243
0.8321	Intermediate Similarity	NPC477536
0.8311	Intermediate Similarity	NPC477691
0.8311	Intermediate Similarity	NPC135522
0.831	Intermediate Similarity	NPC474154
0.8309	Intermediate Similarity	NPC324488
0.8296	Intermediate Similarity	NPC187907
0.8295	Intermediate Similarity	NPC35744
0.8295	Intermediate Similarity	NPC32152
0.8288	Intermediate Similarity	NPC10027
0.8288	Intermediate Similarity	NPC178202
0.8288	Intermediate Similarity	NPC65775
0.8284	Intermediate Similarity	NPC470841
0.8284	Intermediate Similarity	NPC319422
0.8284	Intermediate Similarity	NPC477214
0.8284	Intermediate Similarity	NPC45537
0.8284	Intermediate Similarity	NPC477212
0.8284	Intermediate Similarity	NPC477211
0.8278	Intermediate Similarity	NPC471976
0.8276	Intermediate Similarity	NPC61284
0.8276	Intermediate Similarity	NPC46941
0.8276	Intermediate Similarity	NPC113428
0.8273	Intermediate Similarity	NPC194847
0.8273	Intermediate Similarity	NPC151113
0.8273	Intermediate Similarity	NPC21797
0.8268	Intermediate Similarity	NPC473718
0.8267	Intermediate Similarity	NPC476981
0.8267	Intermediate Similarity	NPC262286
0.8267	Intermediate Similarity	NPC36852
0.8264	Intermediate Similarity	NPC473951
0.8264	Intermediate Similarity	NPC234629
0.8264	Intermediate Similarity	NPC311741
0.8258	Intermediate Similarity	NPC477153
0.8258	Intermediate Similarity	NPC93730
0.8255	Intermediate Similarity	NPC166054
0.8255	Intermediate Similarity	NPC55662
0.8248	Intermediate Similarity	NPC317601
0.8248	Intermediate Similarity	NPC474340
0.8248	Intermediate Similarity	NPC329427
0.8248	Intermediate Similarity	NPC472882
0.8244	Intermediate Similarity	NPC476165
0.8243	Intermediate Similarity	NPC477690
0.8243	Intermediate Similarity	NPC75069
0.8239	Intermediate Similarity	NPC235239
0.8239	Intermediate Similarity	NPC305355
0.8239	Intermediate Similarity	NPC69769
0.8239	Intermediate Similarity	NPC475680
0.8235	Intermediate Similarity	NPC109778
0.8231	Intermediate Similarity	NPC78335
0.8231	Intermediate Similarity	NPC470092
0.8231	Intermediate Similarity	NPC37348
0.8231	Intermediate Similarity	NPC474131
0.8231	Intermediate Similarity	NPC472633
0.8231	Intermediate Similarity	NPC230713
0.8231	Intermediate Similarity	NPC232295
0.8227	Intermediate Similarity	NPC477408
0.8227	Intermediate Similarity	NPC470668
0.8227	Intermediate Similarity	NPC470669
0.8227	Intermediate Similarity	NPC1268
0.8224	Intermediate Similarity	NPC167678
0.8224	Intermediate Similarity	NPC3629
0.8224	Intermediate Similarity	NPC29876
0.8219	Intermediate Similarity	NPC39195
0.8219	Intermediate Similarity	NPC5537
0.8217	Intermediate Similarity	NPC171023
0.8214	Intermediate Similarity	NPC174999
0.8214	Intermediate Similarity	NPC471542
0.8212	Intermediate Similarity	NPC172770
0.8212	Intermediate Similarity	NPC185258
0.8207	Intermediate Similarity	NPC196114
0.8207	Intermediate Similarity	NPC477955
0.8207	Intermediate Similarity	NPC300540
0.8207	Intermediate Similarity	NPC469758
0.82	Intermediate Similarity	NPC142339
0.82	Intermediate Similarity	NPC472453
0.82	Intermediate Similarity	NPC68093
0.82	Intermediate Similarity	NPC191146
0.8195	Intermediate Similarity	NPC56332
0.8194	Intermediate Similarity	NPC38219
0.8194	Intermediate Similarity	NPC477409
0.8194	Intermediate Similarity	NPC219915
0.8188	Intermediate Similarity	NPC475770
0.8188	Intermediate Similarity	NPC287533
0.8188	Intermediate Similarity	NPC470331
0.8188	Intermediate Similarity	NPC290927
0.8188	Intermediate Similarity	NPC472462
0.8182	Intermediate Similarity	NPC147688
0.8182	Intermediate Similarity	NPC156590
0.8182	Intermediate Similarity	NPC118840
0.8182	Intermediate Similarity	NPC205006
0.8182	Intermediate Similarity	NPC302211
0.8182	Intermediate Similarity	NPC64908
0.8176	Intermediate Similarity	NPC170169
0.8175	Intermediate Similarity	NPC205360
0.817	Intermediate Similarity	NPC83922
0.817	Intermediate Similarity	NPC472448
0.817	Intermediate Similarity	NPC329760
0.8169	Intermediate Similarity	NPC477537
0.8169	Intermediate Similarity	NPC23257
0.8168	Intermediate Similarity	NPC45663
0.8163	Intermediate Similarity	NPC294502
0.8163	Intermediate Similarity	NPC70764
0.8163	Intermediate Similarity	NPC200221
0.8158	Intermediate Similarity	NPC476980
0.8158	Intermediate Similarity	NPC204290
0.8154	Intermediate Similarity	NPC54243
0.8151	Intermediate Similarity	NPC473133
0.8151	Intermediate Similarity	NPC71055
0.8151	Intermediate Similarity	NPC308200
0.8151	Intermediate Similarity	NPC91902
0.8151	Intermediate Similarity	NPC47388
0.8151	Intermediate Similarity	NPC470670
0.8148	Intermediate Similarity	NPC22783
0.8146	Intermediate Similarity	NPC79053
0.8146	Intermediate Similarity	NPC44199
0.8146	Intermediate Similarity	NPC78225
0.8146	Intermediate Similarity	NPC217677
0.8146	Intermediate Similarity	NPC236796
0.8146	Intermediate Similarity	NPC165977
0.8143	Intermediate Similarity	NPC474610

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 NPC118253 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	338
0.1-0.2	998
0.2-0.3	1531
0.3-0.4	2668
0.4-0.5	1808
0.5-0.6	1208
0.6-0.7	457
0.7-0.8	134
0.8-0.85	8
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8613	High Similarity	NPD2935	Discontinued
0.8551	High Similarity	NPD2346	Discontinued
0.8507	High Similarity	NPD2313	Discontinued
0.8406	Intermediate Similarity	NPD2799	Discontinued
0.8268	Intermediate Similarity	NPD6671	Approved
0.8156	Intermediate Similarity	NPD2344	Approved
0.8106	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.8074	Intermediate Similarity	NPD2798	Approved
0.8058	Intermediate Similarity	NPD447	Suspended
0.8045	Intermediate Similarity	NPD9717	Approved
0.8041	Intermediate Similarity	NPD3226	Approved
0.8014	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD1203	Approved
0.7947	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7931	Intermediate Similarity	NPD2309	Approved
0.7891	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7881	Intermediate Similarity	NPD6844	Discontinued
0.7842	Intermediate Similarity	NPD411	Approved
0.7829	Intermediate Similarity	NPD2801	Approved
0.7793	Intermediate Similarity	NPD2800	Approved
0.7786	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.774	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.773	Intermediate Similarity	NPD1240	Approved
0.7724	Intermediate Similarity	NPD1549	Phase 2
0.7712	Intermediate Similarity	NPD7819	Suspended
0.7698	Intermediate Similarity	NPD6832	Phase 2
0.7692	Intermediate Similarity	NPD1398	Phase 1
0.7676	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7671	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7655	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7655	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7652	Intermediate Similarity	NPD9493	Approved
0.7652	Intermediate Similarity	NPD7340	Approved
0.7647	Intermediate Similarity	NPD1934	Approved
0.7639	Intermediate Similarity	NPD4308	Phase 3
0.7632	Intermediate Similarity	NPD4380	Phase 2
0.763	Intermediate Similarity	NPD3496	Discontinued
0.7622	Intermediate Similarity	NPD1607	Approved
0.7609	Intermediate Similarity	NPD2797	Approved
0.7609	Intermediate Similarity	NPD1470	Approved
0.7586	Intermediate Similarity	NPD6099	Approved
0.7586	Intermediate Similarity	NPD2796	Approved
0.7586	Intermediate Similarity	NPD6100	Approved
0.7584	Intermediate Similarity	NPD1511	Approved
0.7582	Intermediate Similarity	NPD7411	Suspended
0.758	Intermediate Similarity	NPD5494	Approved
0.7574	Intermediate Similarity	NPD1201	Approved
0.7564	Intermediate Similarity	NPD7075	Discontinued
0.7557	Intermediate Similarity	NPD1241	Discontinued
0.7548	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7548	Intermediate Similarity	NPD5402	Approved
0.7536	Intermediate Similarity	NPD6696	Suspended
0.7533	Intermediate Similarity	NPD2534	Approved
0.7533	Intermediate Similarity	NPD2533	Approved
0.7533	Intermediate Similarity	NPD2532	Approved
0.7532	Intermediate Similarity	NPD6959	Discontinued
0.7517	Intermediate Similarity	NPD1510	Phase 2
0.75	Intermediate Similarity	NPD3882	Suspended
0.75	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD1512	Approved
0.7466	Intermediate Similarity	NPD1551	Phase 2
0.7465	Intermediate Similarity	NPD3268	Approved
0.7451	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7432	Intermediate Similarity	NPD1243	Approved
0.7429	Intermediate Similarity	NPD1019	Discontinued
0.7415	Intermediate Similarity	NPD1471	Phase 3
0.7391	Intermediate Similarity	NPD1481	Phase 2
0.7391	Intermediate Similarity	NPD1608	Approved
0.7389	Intermediate Similarity	NPD7768	Phase 2
0.7383	Intermediate Similarity	NPD3750	Approved
0.7365	Intermediate Similarity	NPD2424	Discontinued
0.7361	Intermediate Similarity	NPD4307	Phase 2
0.7353	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7346	Intermediate Similarity	NPD3446	Phase 1
0.7342	Intermediate Similarity	NPD3749	Approved
0.7342	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7338	Intermediate Similarity	NPD4749	Approved
0.7333	Intermediate Similarity	NPD6559	Discontinued
0.7325	Intermediate Similarity	NPD2296	Approved
0.7319	Intermediate Similarity	NPD1535	Discovery
0.731	Intermediate Similarity	NPD1933	Approved
0.7303	Intermediate Similarity	NPD4662	Approved
0.7303	Intermediate Similarity	NPD4661	Approved
0.7299	Intermediate Similarity	NPD4626	Approved
0.7284	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7284	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7284	Intermediate Similarity	NPD6166	Phase 2
0.7284	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7279	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD4625	Phase 3
0.7267	Intermediate Similarity	NPD7003	Approved
0.7266	Intermediate Similarity	NPD3972	Approved
0.726	Intermediate Similarity	NPD6651	Approved
0.7255	Intermediate Similarity	NPD5049	Phase 3
0.7254	Intermediate Similarity	NPD2861	Phase 2
0.7254	Intermediate Similarity	NPD9494	Approved
0.7246	Intermediate Similarity	NPD8312	Approved
0.7246	Intermediate Similarity	NPD8313	Approved
0.7237	Intermediate Similarity	NPD6799	Approved
0.7234	Intermediate Similarity	NPD1164	Approved
0.7226	Intermediate Similarity	NPD1651	Approved
0.7222	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7208	Intermediate Similarity	NPD920	Approved
0.7206	Intermediate Similarity	NPD7644	Approved
0.7205	Intermediate Similarity	NPD1247	Approved
0.7197	Intermediate Similarity	NPD6801	Discontinued
0.7195	Intermediate Similarity	NPD3818	Discontinued
0.7194	Intermediate Similarity	NPD1611	Approved
0.719	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD6585	Discontinued
0.7176	Intermediate Similarity	NPD74	Approved
0.7176	Intermediate Similarity	NPD9266	Approved
0.7174	Intermediate Similarity	NPD17	Approved
0.7174	Intermediate Similarity	NPD1778	Approved
0.7163	Intermediate Similarity	NPD1283	Approved
0.7163	Intermediate Similarity	NPD1876	Approved
0.7161	Intermediate Similarity	NPD2370	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD6232	Discontinued
0.7154	Intermediate Similarity	NPD968	Approved
0.7152	Intermediate Similarity	NPD4628	Phase 3
0.7152	Intermediate Similarity	NPD5844	Phase 1
0.7152	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6273	Approved
0.7134	Intermediate Similarity	NPD7473	Discontinued
0.7123	Intermediate Similarity	NPD943	Approved
0.7123	Intermediate Similarity	NPD4060	Phase 1
0.7123	Intermediate Similarity	NPD3142	Approved
0.7123	Intermediate Similarity	NPD3140	Approved
0.7115	Intermediate Similarity	NPD2651	Approved
0.7115	Intermediate Similarity	NPD2649	Approved
0.7114	Intermediate Similarity	NPD4476	Approved
0.7114	Intermediate Similarity	NPD4477	Approved
0.7113	Intermediate Similarity	NPD3267	Approved
0.7113	Intermediate Similarity	NPD3266	Approved
0.7108	Intermediate Similarity	NPD7074	Phase 3
0.7107	Intermediate Similarity	NPD3817	Phase 2
0.7105	Intermediate Similarity	NPD3295	Clinical (unspecified phase)
0.7103	Intermediate Similarity	NPD7985	Registered
0.7103	Intermediate Similarity	NPD3764	Approved
0.7103	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD5691	Approved
0.7099	Intermediate Similarity	NPD9267	Approved
0.7099	Intermediate Similarity	NPD9264	Approved
0.7099	Intermediate Similarity	NPD9263	Approved
0.7097	Intermediate Similarity	NPD5403	Approved
0.7092	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.707	Intermediate Similarity	NPD6599	Discontinued
0.7066	Intermediate Similarity	NPD5953	Discontinued
0.7059	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD3300	Phase 2
0.7055	Intermediate Similarity	NPD5710	Approved
0.7055	Intermediate Similarity	NPD5711	Approved
0.7048	Intermediate Similarity	NPD7286	Phase 2
0.7048	Intermediate Similarity	NPD7054	Approved
0.7047	Intermediate Similarity	NPD3748	Approved
0.7047	Intermediate Similarity	NPD7033	Discontinued
0.7035	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7029	Intermediate Similarity	NPD9545	Approved
0.7025	Intermediate Similarity	NPD5889	Approved
0.7025	Intermediate Similarity	NPD5890	Approved
0.7013	Intermediate Similarity	NPD7390	Discontinued
0.7006	Intermediate Similarity	NPD7458	Discontinued
0.7006	Intermediate Similarity	NPD7472	Approved
0.7	Intermediate Similarity	NPD5408	Approved
0.7	Intermediate Similarity	NPD5405	Approved
0.7	Intermediate Similarity	NPD5404	Approved
0.7	Intermediate Similarity	NPD5406	Approved
0.6993	Remote Similarity	NPD2354	Approved
0.6986	Remote Similarity	NPD6798	Discontinued
0.6981	Remote Similarity	NPD6279	Approved
0.6981	Remote Similarity	NPD6280	Approved
0.6978	Remote Similarity	NPD5585	Approved
0.6972	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.6968	Remote Similarity	NPD5401	Approved
0.6964	Remote Similarity	NPD6797	Phase 2
0.6959	Remote Similarity	NPD6355	Discontinued
0.6959	Remote Similarity	NPD4622	Approved
0.6959	Remote Similarity	NPD4618	Approved
0.6954	Remote Similarity	NPD6002	Phase 3
0.6954	Remote Similarity	NPD6004	Phase 3
0.6954	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD6005	Phase 3
0.695	Remote Similarity	NPD1281	Approved
0.695	Remote Similarity	NPD422	Phase 1
0.6947	Remote Similarity	NPD9697	Approved
0.6944	Remote Similarity	NPD5647	Approved
0.6939	Remote Similarity	NPD8032	Phase 2
0.6939	Remote Similarity	NPD6233	Phase 2
0.6937	Remote Similarity	NPD1465	Phase 2
0.6923	Remote Similarity	NPD3225	Approved
0.6923	Remote Similarity	NPD7251	Discontinued
0.6918	Remote Similarity	NPD7095	Approved
0.6906	Remote Similarity	NPD1894	Discontinued

Bioactivity similarity: Similar Natural Products in NPASS

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

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

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data