NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	402.17
Volume:	406.475
LogP:	1.891
LogD:	1.564
LogS:	-3.035
# Rotatable Bonds:	3
TPSA:	117.95
# H-Bond Aceptor:	7
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.81
Synthetic Accessibility Score:	4.505
Fsp3:	0.5
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-4.79
MDCK Permeability:	1.216795135405846e-05
Pgp-inhibitor:	0.004
Pgp-substrate:	0.78
Human Intestinal Absorption (HIA):	0.065
20% Bioavailability (F20%):	0.008
30% Bioavailability (F30%):	0.011

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.175
Plasma Protein Binding (PPB):	93.1108169555664%
Volume Distribution (VD):	0.47
Pgp-substrate:	6.55308198928833%

ADMET: Metabolism

CYP1A2-inhibitor:	0.028
CYP1A2-substrate:	0.957
CYP2C19-inhibitor:	0.062
CYP2C19-substrate:	0.917
CYP2C9-inhibitor:	0.472
CYP2C9-substrate:	0.789
CYP2D6-inhibitor:	0.003
CYP2D6-substrate:	0.208
CYP3A4-inhibitor:	0.754
CYP3A4-substrate:	0.903

ADMET: Excretion

Clearance (CL):	1.495
Half-life (T1/2):	0.464

ADMET: Toxicity

hERG Blockers:	0.001
Human Hepatotoxicity (H-HT):	0.924
Drug-inuced Liver Injury (DILI):	0.962
AMES Toxicity:	0.016
Rat Oral Acute Toxicity:	0.835
Maximum Recommended Daily Dose:	0.548
Skin Sensitization:	0.256
Carcinogencity:	0.145
Eye Corrosion:	0.003
Eye Irritation:	0.021
Respiratory Toxicity:	0.382

Download Data

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

Natural Product: NPC478233

Natural Product ID:	NPC478233
*Common Name:**	Lecanicillolide
IUPAC Name:	(5S,8R)-8-ethyl-5-(4-hydroxy-5,6-dimethyl-2-oxopyran-3-yl)-2,3,8-trimethyl-5,6-dihydrochromene-4,7-dione
Synonyms:
Standard InCHIKey:	IQOQYVAMVLWEDE-ZSEKCTLFSA-N
Standard InCHI:	InChI=1S/C21H24O6/c1-7-21(6)14(22)8-13(15-17(23)9(2)11(4)26-19(15)21)16-18(24)10(3)12(5)27-20(16)25/h13,24H,7-8H2,1-6H3/t13-,21-/m0/s1
SMILES:	CC[C@]1(C(=O)C[C@@H](C2=C1OC(=C(C2=O)C)C)C3=C(C(=C(OC3=O)C)C)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	132937868
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000086] Pyrans [CHEMONTID:0000481] Pyranones 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
NPO33702	Lecanicillium sp. PR-M-3	Species	Cordycipitaceae	Eukaryota	n.a.	isolated from the rhizosphere soil of puer tea at Puer in Yunnan, China	2011-SEP	DOI[10.1016/j.tetlet.2017.01.023]

☑ 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

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference

☑ 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 NPC478233 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	337
0.1-0.2	1664
0.2-0.3	3405
0.3-0.4	8132
0.4-0.5	11548
0.5-0.6	5461
0.6-0.7	6855
0.7-0.8	4999
0.8-0.85	284
0.85-0.9	12
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8265	Intermediate Similarity	NPC476797
0.8105	Intermediate Similarity	NPC143025
0.7959	Intermediate Similarity	NPC271652
0.7895	Intermediate Similarity	NPC229717
0.785	Intermediate Similarity	NPC478209
0.7843	Intermediate Similarity	NPC54705
0.7822	Intermediate Similarity	NPC53844
0.7822	Intermediate Similarity	NPC208094
0.781	Intermediate Similarity	NPC478208
0.7802	Intermediate Similarity	NPC315765
0.78	Intermediate Similarity	NPC209355
0.7767	Intermediate Similarity	NPC244456
0.7767	Intermediate Similarity	NPC469657
0.7755	Intermediate Similarity	NPC476369
0.7755	Intermediate Similarity	NPC476437
0.7755	Intermediate Similarity	NPC51486
0.77	Intermediate Similarity	NPC53685
0.7692	Intermediate Similarity	NPC469606
0.7692	Intermediate Similarity	NPC31058
0.7692	Intermediate Similarity	NPC273005
0.7692	Intermediate Similarity	NPC235369
0.7685	Intermediate Similarity	NPC478211
0.7677	Intermediate Similarity	NPC472705
0.7664	Intermediate Similarity	NPC220155
0.7653	Intermediate Similarity	NPC5509
0.7647	Intermediate Similarity	NPC121339
0.7642	Intermediate Similarity	NPC469607
0.7636	Intermediate Similarity	NPC478212
0.7624	Intermediate Similarity	NPC295347
0.7619	Intermediate Similarity	NPC320154
0.7619	Intermediate Similarity	NPC291154
0.7615	Intermediate Similarity	NPC247031
0.7615	Intermediate Similarity	NPC100329
0.7615	Intermediate Similarity	NPC132790
0.7615	Intermediate Similarity	NPC97939
0.76	Intermediate Similarity	NPC115021
0.7593	Intermediate Similarity	NPC228477
0.7593	Intermediate Similarity	NPC137911
0.7593	Intermediate Similarity	NPC478210
0.7576	Intermediate Similarity	NPC213636
0.7576	Intermediate Similarity	NPC113393
0.7576	Intermediate Similarity	NPC253177
0.7576	Intermediate Similarity	NPC280592
0.7553	Intermediate Similarity	NPC282293
0.7551	Intermediate Similarity	NPC307298
0.7551	Intermediate Similarity	NPC472302
0.7551	Intermediate Similarity	NPC72397
0.7551	Intermediate Similarity	NPC476796
0.7549	Intermediate Similarity	NPC17578
0.7549	Intermediate Similarity	NPC240673
0.7549	Intermediate Similarity	NPC202833
0.7549	Intermediate Similarity	NPC3772
0.7547	Intermediate Similarity	NPC121099
0.7525	Intermediate Similarity	NPC476415
0.7525	Intermediate Similarity	NPC184870
0.7525	Intermediate Similarity	NPC474555
0.7524	Intermediate Similarity	NPC80781
0.7522	Intermediate Similarity	NPC108581
0.7522	Intermediate Similarity	NPC478205
0.7522	Intermediate Similarity	NPC478206
0.75	Intermediate Similarity	NPC472814
0.75	Intermediate Similarity	NPC307954
0.75	Intermediate Similarity	NPC478216
0.75	Intermediate Similarity	NPC177037
0.75	Intermediate Similarity	NPC471329
0.75	Intermediate Similarity	NPC476299
0.75	Intermediate Similarity	NPC476767
0.75	Intermediate Similarity	NPC117685
0.75	Intermediate Similarity	NPC198880
0.75	Intermediate Similarity	NPC296114
0.75	Intermediate Similarity	NPC474012
0.7477	Intermediate Similarity	NPC266570
0.7477	Intermediate Similarity	NPC472935
0.7477	Intermediate Similarity	NPC475966
0.7476	Intermediate Similarity	NPC106557
0.7475	Intermediate Similarity	NPC280833
0.7475	Intermediate Similarity	NPC284561
0.7455	Intermediate Similarity	NPC324683
0.7455	Intermediate Similarity	NPC474315
0.7453	Intermediate Similarity	NPC159533
0.7453	Intermediate Similarity	NPC95899
0.7451	Intermediate Similarity	NPC37646
0.7449	Intermediate Similarity	NPC125925
0.7449	Intermediate Similarity	NPC220930
0.7449	Intermediate Similarity	NPC113370
0.7449	Intermediate Similarity	NPC312561
0.7449	Intermediate Similarity	NPC476079
0.7449	Intermediate Similarity	NPC272039
0.7449	Intermediate Similarity	NPC103743
0.7449	Intermediate Similarity	NPC476409
0.7434	Intermediate Similarity	NPC478204
0.7431	Intermediate Similarity	NPC23497
0.7429	Intermediate Similarity	NPC471075
0.7426	Intermediate Similarity	NPC476416
0.7426	Intermediate Similarity	NPC131840
0.7423	Intermediate Similarity	NPC307112
0.7407	Intermediate Similarity	NPC91034
0.7404	Intermediate Similarity	NPC316598
0.7404	Intermediate Similarity	NPC23364
0.74	Intermediate Similarity	NPC212679
0.74	Intermediate Similarity	NPC145666
0.74	Intermediate Similarity	NPC469595
0.74	Intermediate Similarity	NPC220454
0.74	Intermediate Similarity	NPC281942
0.74	Intermediate Similarity	NPC232426
0.7396	Intermediate Similarity	NPC258985
0.7396	Intermediate Similarity	NPC102197
0.7387	Intermediate Similarity	NPC285956
0.7379	Intermediate Similarity	NPC242848
0.7379	Intermediate Similarity	NPC243525
0.7379	Intermediate Similarity	NPC40765
0.7379	Intermediate Similarity	NPC7124
0.7374	Intermediate Similarity	NPC53454
0.7374	Intermediate Similarity	NPC24816
0.7364	Intermediate Similarity	NPC470496
0.7364	Intermediate Similarity	NPC206595
0.7358	Intermediate Similarity	NPC475320
0.7358	Intermediate Similarity	NPC295791
0.7358	Intermediate Similarity	NPC476890
0.7358	Intermediate Similarity	NPC137430
0.7358	Intermediate Similarity	NPC281702
0.7353	Intermediate Similarity	NPC474554
0.7353	Intermediate Similarity	NPC84893
0.7347	Intermediate Similarity	NPC477478
0.7347	Intermediate Similarity	NPC322159
0.7347	Intermediate Similarity	NPC474062
0.7347	Intermediate Similarity	NPC477479
0.7339	Intermediate Similarity	NPC151393
0.7339	Intermediate Similarity	NPC89171
0.7339	Intermediate Similarity	NPC476765
0.7339	Intermediate Similarity	NPC476802
0.7333	Intermediate Similarity	NPC306856
0.7333	Intermediate Similarity	NPC299971
0.7333	Intermediate Similarity	NPC144660
0.7327	Intermediate Similarity	NPC141831
0.7321	Intermediate Similarity	NPC321496
0.732	Intermediate Similarity	NPC149869
0.7315	Intermediate Similarity	NPC189863
0.7312	Intermediate Similarity	NPC316324
0.7308	Intermediate Similarity	NPC474343
0.7308	Intermediate Similarity	NPC287668
0.7308	Intermediate Similarity	NPC253826
0.7308	Intermediate Similarity	NPC122294
0.7308	Intermediate Similarity	NPC475709
0.73	Intermediate Similarity	NPC118011
0.73	Intermediate Similarity	NPC36668
0.729	Intermediate Similarity	NPC8196
0.729	Intermediate Similarity	NPC99266
0.729	Intermediate Similarity	NPC271059
0.729	Intermediate Similarity	NPC476889
0.729	Intermediate Similarity	NPC25666
0.7281	Intermediate Similarity	NPC98249
0.7281	Intermediate Similarity	NPC53396
0.7273	Intermediate Similarity	NPC286174
0.7273	Intermediate Similarity	NPC31522
0.7273	Intermediate Similarity	NPC77947
0.7273	Intermediate Similarity	NPC477228
0.7265	Intermediate Similarity	NPC287236
0.7264	Intermediate Similarity	NPC323441
0.7264	Intermediate Similarity	NPC476888
0.7264	Intermediate Similarity	NPC472924
0.7264	Intermediate Similarity	NPC472637
0.7264	Intermediate Similarity	NPC93744
0.7264	Intermediate Similarity	NPC475099
0.7255	Intermediate Similarity	NPC476049
0.7248	Intermediate Similarity	NPC112780
0.7248	Intermediate Similarity	NPC202524
0.7248	Intermediate Similarity	NPC473037
0.7245	Intermediate Similarity	NPC86316
0.7245	Intermediate Similarity	NPC106416
0.7245	Intermediate Similarity	NPC65661
0.7245	Intermediate Similarity	NPC189311
0.7245	Intermediate Similarity	NPC76333
0.7241	Intermediate Similarity	NPC476962
0.7238	Intermediate Similarity	NPC16021
0.7238	Intermediate Similarity	NPC471717
0.7232	Intermediate Similarity	NPC90952
0.7232	Intermediate Similarity	NPC66108
0.7228	Intermediate Similarity	NPC477147
0.7228	Intermediate Similarity	NPC232202
0.7228	Intermediate Similarity	NPC469372
0.7228	Intermediate Similarity	NPC472307
0.7228	Intermediate Similarity	NPC477782
0.7228	Intermediate Similarity	NPC477149
0.7222	Intermediate Similarity	NPC296950
0.7222	Intermediate Similarity	NPC239162
0.7222	Intermediate Similarity	NPC325769
0.7222	Intermediate Similarity	NPC146731
0.7217	Intermediate Similarity	NPC284707
0.7216	Intermediate Similarity	NPC475083
0.7216	Intermediate Similarity	NPC49019
0.7212	Intermediate Similarity	NPC328371
0.7212	Intermediate Similarity	NPC184065
0.7212	Intermediate Similarity	NPC472941
0.7212	Intermediate Similarity	NPC456
0.7212	Intermediate Similarity	NPC234993
0.7212	Intermediate Similarity	NPC134072
0.7207	Intermediate Similarity	NPC29133
0.7207	Intermediate Similarity	NPC129689
0.7207	Intermediate Similarity	NPC286880

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 NPC478233 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	295
0.1-0.2	1126
0.2-0.3	2001
0.3-0.4	2604
0.4-0.5	1954
0.5-0.6	818
0.6-0.7	266
0.7-0.8	83
0.8-0.85	3
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7255	Intermediate Similarity	NPD5779	Approved
0.7255	Intermediate Similarity	NPD5778	Approved
0.7157	Intermediate Similarity	NPD6411	Approved
0.708	Intermediate Similarity	NPD6053	Discontinued
0.7009	Intermediate Similarity	NPD7640	Approved
0.7009	Intermediate Similarity	NPD7639	Approved
0.6961	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6961	Remote Similarity	NPD6101	Approved
0.6939	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6916	Remote Similarity	NPD7638	Approved
0.6881	Remote Similarity	NPD7632	Discontinued
0.6838	Remote Similarity	NPD7115	Discovery
0.6814	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6796	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6759	Remote Similarity	NPD4225	Approved
0.6759	Remote Similarity	NPD5696	Approved
0.6731	Remote Similarity	NPD5785	Approved
0.6726	Remote Similarity	NPD6686	Approved
0.6698	Remote Similarity	NPD7748	Approved
0.6667	Remote Similarity	NPD5279	Phase 3
0.6667	Remote Similarity	NPD6083	Phase 2
0.6667	Remote Similarity	NPD6084	Phase 2
0.6667	Remote Similarity	NPD7515	Phase 2
0.6636	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6636	Remote Similarity	NPD5695	Phase 3
0.6609	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6569	Remote Similarity	NPD1694	Approved
0.6566	Remote Similarity	NPD4695	Discontinued
0.6562	Remote Similarity	NPD8039	Approved
0.6538	Remote Similarity	NPD5737	Approved
0.6538	Remote Similarity	NPD6672	Approved
0.6535	Remote Similarity	NPD7260	Phase 2
0.6531	Remote Similarity	NPD3617	Approved
0.6514	Remote Similarity	NPD7902	Approved
0.6509	Remote Similarity	NPD5281	Approved
0.6509	Remote Similarity	NPD7983	Approved
0.6509	Remote Similarity	NPD5284	Approved
0.6509	Remote Similarity	NPD7637	Suspended
0.6509	Remote Similarity	NPD5693	Phase 1
0.6505	Remote Similarity	NPD7146	Approved
0.6505	Remote Similarity	NPD6409	Approved
0.6505	Remote Similarity	NPD7334	Approved
0.6505	Remote Similarity	NPD7521	Approved
0.6505	Remote Similarity	NPD5330	Approved
0.6505	Remote Similarity	NPD6684	Approved
0.6484	Remote Similarity	NPD6845	Suspended
0.6471	Remote Similarity	NPD3133	Approved
0.6471	Remote Similarity	NPD3665	Phase 1
0.6471	Remote Similarity	NPD3666	Approved
0.6466	Remote Similarity	NPD6371	Approved
0.6449	Remote Similarity	NPD6399	Phase 3
0.6436	Remote Similarity	NPD5209	Approved
0.6429	Remote Similarity	NPD4756	Discovery
0.6422	Remote Similarity	NPD7614	Phase 1
0.6415	Remote Similarity	NPD6698	Approved
0.6415	Remote Similarity	NPD46	Approved
0.6415	Remote Similarity	NPD5692	Phase 3
0.6404	Remote Similarity	NPD6402	Approved
0.6404	Remote Similarity	NPD7128	Approved
0.6404	Remote Similarity	NPD5739	Approved
0.6404	Remote Similarity	NPD6675	Approved
0.6389	Remote Similarity	NPD5282	Discontinued
0.6381	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6381	Remote Similarity	NPD6903	Approved
0.6355	Remote Similarity	NPD6050	Approved
0.6355	Remote Similarity	NPD5694	Approved
0.6348	Remote Similarity	NPD5701	Approved
0.6348	Remote Similarity	NPD5697	Approved
0.6348	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6346	Remote Similarity	NPD3618	Phase 1
0.6346	Remote Similarity	NPD4519	Discontinued
0.6346	Remote Similarity	NPD4623	Approved
0.6346	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.633	Remote Similarity	NPD5210	Approved
0.633	Remote Similarity	NPD4629	Approved
0.6321	Remote Similarity	NPD4753	Phase 2
0.6321	Remote Similarity	NPD5328	Approved
0.6311	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6293	Remote Similarity	NPD7320	Approved
0.6293	Remote Similarity	NPD6899	Approved
0.6293	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6293	Remote Similarity	NPD6011	Approved
0.6293	Remote Similarity	NPD6881	Approved
0.6286	Remote Similarity	NPD3573	Approved
0.6275	Remote Similarity	NPD3667	Approved
0.6273	Remote Similarity	NPD7839	Suspended
0.6273	Remote Similarity	NPD7732	Phase 3
0.6262	Remote Similarity	NPD5207	Approved
0.626	Remote Similarity	NPD6319	Approved
0.625	Remote Similarity	NPD1696	Phase 3
0.625	Remote Similarity	NPD5363	Approved
0.6239	Remote Similarity	NPD6012	Approved
0.6239	Remote Similarity	NPD6014	Approved
0.6239	Remote Similarity	NPD6373	Approved
0.6239	Remote Similarity	NPD7900	Approved
0.6239	Remote Similarity	NPD6372	Approved
0.6239	Remote Similarity	NPD6013	Approved
0.6239	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6214	Remote Similarity	NPD7154	Phase 3
0.621	Remote Similarity	NPD8513	Phase 3
0.621	Remote Similarity	NPD7503	Approved
0.6207	Remote Similarity	NPD6412	Phase 2
0.6204	Remote Similarity	NPD6079	Approved
0.62	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.619	Remote Similarity	NPD5280	Approved
0.619	Remote Similarity	NPD4694	Approved
0.619	Remote Similarity	NPD5786	Approved
0.6186	Remote Similarity	NPD7290	Approved
0.6186	Remote Similarity	NPD7102	Approved
0.6186	Remote Similarity	NPD6883	Approved
0.6182	Remote Similarity	NPD5654	Approved
0.6168	Remote Similarity	NPD6080	Approved
0.6168	Remote Similarity	NPD6904	Approved
0.6168	Remote Similarity	NPD6673	Approved
0.6167	Remote Similarity	NPD4632	Approved
0.6161	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD4786	Approved
0.614	Remote Similarity	NPD5211	Phase 2
0.6134	Remote Similarity	NPD6650	Approved
0.6134	Remote Similarity	NPD6617	Approved
0.6134	Remote Similarity	NPD8130	Phase 1
0.6134	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6134	Remote Similarity	NPD6847	Approved
0.6134	Remote Similarity	NPD6649	Approved
0.6134	Remote Similarity	NPD6869	Approved
0.6129	Remote Similarity	NPD7341	Phase 2
0.6126	Remote Similarity	NPD4697	Phase 3
0.6126	Remote Similarity	NPD5221	Approved
0.6126	Remote Similarity	NPD5222	Approved
0.6126	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6124	Remote Similarity	NPD7319	Approved
0.6121	Remote Similarity	NPD6008	Approved
0.6117	Remote Similarity	NPD4221	Approved
0.6117	Remote Similarity	NPD4269	Approved
0.6117	Remote Similarity	NPD4223	Phase 3
0.6117	Remote Similarity	NPD4270	Approved
0.6111	Remote Similarity	NPD8328	Phase 3
0.6111	Remote Similarity	NPD7838	Discovery
0.6106	Remote Similarity	NPD6404	Discontinued
0.6102	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6083	Remote Similarity	NPD6882	Approved
0.6083	Remote Similarity	NPD8297	Approved
0.608	Remote Similarity	NPD8516	Approved
0.608	Remote Similarity	NPD8515	Approved
0.608	Remote Similarity	NPD8517	Approved
0.6075	Remote Similarity	NPD5208	Approved
0.6071	Remote Similarity	NPD4755	Approved
0.6071	Remote Similarity	NPD5959	Approved
0.6071	Remote Similarity	NPD5173	Approved
0.6064	Remote Similarity	NPD3704	Approved
0.6063	Remote Similarity	NPD7492	Approved
0.6058	Remote Similarity	NPD6110	Phase 1
0.6036	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6034	Remote Similarity	NPD5141	Approved
0.6034	Remote Similarity	NPD5909	Discontinued
0.6032	Remote Similarity	NPD2838	Clinical (unspecified phase)
0.6016	Remote Similarity	NPD6009	Approved
0.6016	Remote Similarity	NPD7507	Approved
0.6016	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6016	Remote Similarity	NPD6616	Approved
0.6	Remote Similarity	NPD4202	Approved
0.6	Remote Similarity	NPD6059	Approved
0.6	Remote Similarity	NPD6054	Approved
0.6	Remote Similarity	NPD4197	Approved
0.5969	Remote Similarity	NPD8293	Discontinued
0.5969	Remote Similarity	NPD7078	Approved
0.5965	Remote Similarity	NPD4700	Approved
0.5965	Remote Similarity	NPD5286	Approved
0.5965	Remote Similarity	NPD4696	Approved
0.5965	Remote Similarity	NPD5285	Approved
0.5963	Remote Similarity	NPD4096	Approved
0.5962	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.5954	Remote Similarity	NPD6914	Discontinued
0.5952	Remote Similarity	NPD5983	Phase 2
0.5952	Remote Similarity	NPD6016	Approved
0.5952	Remote Similarity	NPD6015	Approved
0.5943	Remote Similarity	NPD5329	Approved
0.5935	Remote Similarity	NPD6868	Approved
0.5935	Remote Similarity	NPD6274	Approved
0.5932	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.5926	Remote Similarity	NPD4518	Approved
0.5923	Remote Similarity	NPD7736	Approved
0.5922	Remote Similarity	NPD4252	Approved
0.5922	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.5917	Remote Similarity	NPD4634	Approved
0.5913	Remote Similarity	NPD5223	Approved
0.5906	Remote Similarity	NPD5988	Approved
0.5906	Remote Similarity	NPD6370	Approved
0.5905	Remote Similarity	NPD5362	Discontinued
0.5905	Remote Similarity	NPD4788	Approved
0.5888	Remote Similarity	NPD5690	Phase 2
0.5888	Remote Similarity	NPD4689	Approved
0.5888	Remote Similarity	NPD4688	Approved
0.5888	Remote Similarity	NPD4693	Phase 3
0.5888	Remote Similarity	NPD4138	Approved
0.5888	Remote Similarity	NPD4249	Approved
0.5888	Remote Similarity	NPD4690	Approved
0.5888	Remote Similarity	NPD5205	Approved
0.5888	Remote Similarity	NPD6098	Approved
0.5887	Remote Similarity	NPD6317	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