NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	234.16
Volume:	266.474
LogP:	4.074
LogD:	3.891
LogS:	-3.682
# Rotatable Bonds:	5
TPSA:	40.46
# H-Bond Aceptor:	2
# H-Bond Donor:	2
# Rings:	1
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.815
Synthetic Accessibility Score:	2.483
Fsp3:	0.467
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:	-4.347
MDCK Permeability:	2.179811599489767e-05
Pgp-inhibitor:	0.014
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.067
30% Bioavailability (F30%):	0.188

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.971
Plasma Protein Binding (PPB):	92.7613296508789%
Volume Distribution (VD):	3.017
Pgp-substrate:	12.129897117614746%

ADMET: Metabolism

CYP1A2-inhibitor:	0.887
CYP1A2-substrate:	0.859
CYP2C19-inhibitor:	0.813
CYP2C19-substrate:	0.328
CYP2C9-inhibitor:	0.764
CYP2C9-substrate:	0.92
CYP2D6-inhibitor:	0.8
CYP2D6-substrate:	0.538
CYP3A4-inhibitor:	0.392
CYP3A4-substrate:	0.323

ADMET: Excretion

Clearance (CL):	9.966
Half-life (T1/2):	0.669

ADMET: Toxicity

hERG Blockers:	0.015
Human Hepatotoxicity (H-HT):	0.047
Drug-inuced Liver Injury (DILI):	0.09
AMES Toxicity:	0.04
Rat Oral Acute Toxicity:	0.111
Maximum Recommended Daily Dose:	0.197
Skin Sensitization:	0.446
Carcinogencity:	0.046
Eye Corrosion:	0.008
Eye Irritation:	0.87
Respiratory Toxicity:	0.135

Download Data

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

Natural Product: NPC235762

Natural Product ID:	NPC235762
*Common Name:**	Aspergillusene A
IUPAC Name:	5-(hydroxymethyl)-2-[(E)-6-methylhept-2-en-2-yl]phenol
Synonyms:	Aspergillusene A
Standard InCHIKey:	NWPUHDAIOGMKFI-WUXMJOGZSA-N
Standard InCHI:	InChI=1S/C15H22O2/c1-11(2)5-4-6-12(3)14-8-7-13(10-16)9-15(14)17/h6-9,11,16-17H,4-5,10H2,1-3H3/b12-6+
SMILES:	OCc1ccc(c(c1)O)/C(=C/CCC(C)C)/C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1812022
PubChem CID:	53468690
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001550] Sesquiterpenoids

*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
NPO31451	Aspergillus sydowii	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18505285]
NPO31451	Aspergillus sydowii	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21718031]
NPO31451	Aspergillus sydowii	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23647825]
NPO31451	Aspergillus sydowii	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24057165]

☑ 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
Others	2

Activity Type	# Activity
NON-MOLECULAR	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	84.26	%	PMID[529490]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	8800.0	nM	PMID[529490]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	97.79	%	PMID[529490]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	6110.0	nM	PMID[529490]

☑ 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 NPC235762 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	229
0.1-0.2	1325
0.2-0.3	3882
0.3-0.4	12968
0.4-0.5	7259
0.5-0.6	10235
0.6-0.7	5186
0.7-0.8	1248
0.8-0.85	236
0.85-0.9	102
0.9-0.95	22
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC471228
0.9896	High Similarity	NPC475225
0.9789	High Similarity	NPC174911
0.9596	High Similarity	NPC66834
0.9381	High Similarity	NPC72729
0.9375	High Similarity	NPC79241
0.9375	High Similarity	NPC6597
0.9375	High Similarity	NPC474073
0.9271	High Similarity	NPC312132
0.9271	High Similarity	NPC259512
0.9135	High Similarity	NPC228452
0.9126	High Similarity	NPC132720
0.9091	High Similarity	NPC477685
0.9082	High Similarity	NPC33675
0.9082	High Similarity	NPC299762
0.9053	High Similarity	NPC231150
0.902	High Similarity	NPC474352
0.901	High Similarity	NPC47284
0.899	High Similarity	NPC248396
0.899	High Similarity	NPC48730
0.899	High Similarity	NPC130103
0.899	High Similarity	NPC129373
0.898	High Similarity	NPC152097
0.8952	High Similarity	NPC302371
0.8952	High Similarity	NPC26615
0.8947	High Similarity	NPC312304
0.8922	High Similarity	NPC53740
0.8911	High Similarity	NPC323810
0.89	High Similarity	NPC252105
0.89	High Similarity	NPC80800
0.8889	High Similarity	NPC260775
0.8889	High Similarity	NPC128723
0.8868	High Similarity	NPC190212
0.8846	High Similarity	NPC473524
0.8812	High Similarity	NPC108497
0.88	High Similarity	NPC70677
0.88	High Similarity	NPC130756
0.88	High Similarity	NPC12931
0.88	High Similarity	NPC294741
0.8788	High Similarity	NPC88420
0.8788	High Similarity	NPC475078
0.8763	High Similarity	NPC147284
0.8763	High Similarity	NPC94139
0.8763	High Similarity	NPC3358
0.8763	High Similarity	NPC306884
0.8763	High Similarity	NPC29373
0.8763	High Similarity	NPC162314
0.8763	High Similarity	NPC210497
0.875	High Similarity	NPC192
0.8738	High Similarity	NPC310456
0.8737	High Similarity	NPC27974
0.8725	High Similarity	NPC475580
0.8725	High Similarity	NPC218879
0.8725	High Similarity	NPC272029
0.8725	High Similarity	NPC244513
0.8725	High Similarity	NPC227458
0.8713	High Similarity	NPC12221
0.8692	High Similarity	NPC319803
0.8692	High Similarity	NPC261343
0.8679	High Similarity	NPC54373
0.8673	High Similarity	NPC245187
0.8673	High Similarity	NPC152415
0.8654	High Similarity	NPC158253
0.8654	High Similarity	NPC320439
0.8654	High Similarity	NPC204901
0.8654	High Similarity	NPC232523
0.8641	High Similarity	NPC37802
0.8641	High Similarity	NPC471350
0.8641	High Similarity	NPC117115
0.8632	High Similarity	NPC407
0.8632	High Similarity	NPC307235
0.8627	High Similarity	NPC269212
0.8624	High Similarity	NPC469663
0.8624	High Similarity	NPC92
0.8611	High Similarity	NPC41851
0.86	High Similarity	NPC77492
0.8571	High Similarity	NPC306295
0.8571	High Similarity	NPC174981
0.8571	High Similarity	NPC64586
0.8571	High Similarity	NPC325292
0.8571	High Similarity	NPC55903
0.8571	High Similarity	NPC138117
0.8559	High Similarity	NPC151197
0.8558	High Similarity	NPC469913
0.8558	High Similarity	NPC12640
0.8558	High Similarity	NPC155072
0.8558	High Similarity	NPC21594
0.8558	High Similarity	NPC201662
0.8558	High Similarity	NPC99836
0.8557	High Similarity	NPC300017
0.8557	High Similarity	NPC47950
0.8545	High Similarity	NPC477136
0.8545	High Similarity	NPC320864
0.8544	High Similarity	NPC130817
0.8532	High Similarity	NPC192948
0.8532	High Similarity	NPC232165
0.8532	High Similarity	NPC35797
0.8526	High Similarity	NPC155393
0.8505	High Similarity	NPC77772
0.8505	High Similarity	NPC224527
0.8505	High Similarity	NPC469912
0.8505	High Similarity	NPC266937
0.8505	High Similarity	NPC470770
0.8491	Intermediate Similarity	NPC186385
0.8491	Intermediate Similarity	NPC98392
0.8491	Intermediate Similarity	NPC58865
0.8491	Intermediate Similarity	NPC33728
0.8491	Intermediate Similarity	NPC19808
0.8491	Intermediate Similarity	NPC299568
0.8485	Intermediate Similarity	NPC76938
0.8476	Intermediate Similarity	NPC151477
0.8476	Intermediate Similarity	NPC233320
0.8476	Intermediate Similarity	NPC61033
0.8476	Intermediate Similarity	NPC305603
0.8469	Intermediate Similarity	NPC304541
0.8469	Intermediate Similarity	NPC306074
0.8468	Intermediate Similarity	NPC48781
0.8468	Intermediate Similarity	NPC9592
0.8455	Intermediate Similarity	NPC477137
0.8455	Intermediate Similarity	NPC308828
0.8455	Intermediate Similarity	NPC308311
0.8455	Intermediate Similarity	NPC38893
0.8455	Intermediate Similarity	NPC219112
0.8454	Intermediate Similarity	NPC258219
0.8454	Intermediate Similarity	NPC318325
0.8454	Intermediate Similarity	NPC123273
0.8454	Intermediate Similarity	NPC242240
0.844	Intermediate Similarity	NPC268160
0.8426	Intermediate Similarity	NPC177962
0.8426	Intermediate Similarity	NPC228425
0.8426	Intermediate Similarity	NPC473521
0.8426	Intermediate Similarity	NPC62867
0.8421	Intermediate Similarity	NPC286904
0.8421	Intermediate Similarity	NPC150837
0.84	Intermediate Similarity	NPC32714
0.84	Intermediate Similarity	NPC8392
0.84	Intermediate Similarity	NPC222146
0.84	Intermediate Similarity	NPC274678
0.84	Intermediate Similarity	NPC313650
0.8396	Intermediate Similarity	NPC262365
0.8393	Intermediate Similarity	NPC469644
0.8393	Intermediate Similarity	NPC160235
0.8378	Intermediate Similarity	NPC304510
0.8378	Intermediate Similarity	NPC172219
0.8365	Intermediate Similarity	NPC238696
0.8364	Intermediate Similarity	NPC147179
0.8351	Intermediate Similarity	NPC113460
0.8351	Intermediate Similarity	NPC25493
0.8351	Intermediate Similarity	NPC104216
0.8351	Intermediate Similarity	NPC1793
0.8351	Intermediate Similarity	NPC19680
0.835	Intermediate Similarity	NPC110764
0.8349	Intermediate Similarity	NPC296144
0.8349	Intermediate Similarity	NPC28784
0.8333	Intermediate Similarity	NPC51333
0.8333	Intermediate Similarity	NPC122005
0.8333	Intermediate Similarity	NPC252821
0.8333	Intermediate Similarity	NPC78119
0.8333	Intermediate Similarity	NPC275627
0.8333	Intermediate Similarity	NPC132078
0.8333	Intermediate Similarity	NPC216468
0.8333	Intermediate Similarity	NPC151537
0.8319	Intermediate Similarity	NPC328485
0.8317	Intermediate Similarity	NPC473388
0.8304	Intermediate Similarity	NPC154030
0.8304	Intermediate Similarity	NPC471671
0.8304	Intermediate Similarity	NPC206205
0.8304	Intermediate Similarity	NPC41567
0.8304	Intermediate Similarity	NPC469609
0.83	Intermediate Similarity	NPC128062
0.83	Intermediate Similarity	NPC316301
0.83	Intermediate Similarity	NPC27323
0.83	Intermediate Similarity	NPC289769
0.8286	Intermediate Similarity	NPC138942
0.8283	Intermediate Similarity	NPC204210
0.8273	Intermediate Similarity	NPC473931
0.8273	Intermediate Similarity	NPC474050
0.8273	Intermediate Similarity	NPC474114
0.8273	Intermediate Similarity	NPC197513
0.8269	Intermediate Similarity	NPC302219
0.8269	Intermediate Similarity	NPC71002
0.8269	Intermediate Similarity	NPC242342
0.8269	Intermediate Similarity	NPC94351
0.8269	Intermediate Similarity	NPC249828
0.8269	Intermediate Similarity	NPC313030
0.8269	Intermediate Similarity	NPC146798
0.8269	Intermediate Similarity	NPC24327
0.8269	Intermediate Similarity	NPC12870
0.8269	Intermediate Similarity	NPC53051
0.8269	Intermediate Similarity	NPC85479
0.8269	Intermediate Similarity	NPC24404
0.8269	Intermediate Similarity	NPC106396
0.8269	Intermediate Similarity	NPC168303
0.8269	Intermediate Similarity	NPC222522
0.8269	Intermediate Similarity	NPC233827
0.8265	Intermediate Similarity	NPC280347
0.8265	Intermediate Similarity	NPC177420
0.8257	Intermediate Similarity	NPC166995
0.8257	Intermediate Similarity	NPC46940
0.8257	Intermediate Similarity	NPC250323

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 NPC235762 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	216
0.1-0.2	969
0.2-0.3	1432
0.3-0.4	2876
0.4-0.5	1910
0.5-0.6	1166
0.6-0.7	489
0.7-0.8	78
0.8-0.85	10
0.85-0.9	2
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9368	High Similarity	NPD844	Approved
0.9271	High Similarity	NPD288	Approved
0.88	High Similarity	NPD289	Clinical (unspecified phase)
0.8571	High Similarity	NPD845	Approved
0.8491	Intermediate Similarity	NPD4750	Phase 3
0.8426	Intermediate Similarity	NPD7635	Approved
0.8333	Intermediate Similarity	NPD3020	Approved
0.83	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.8218	Intermediate Similarity	NPD2859	Approved
0.8218	Intermediate Similarity	NPD2860	Approved
0.8173	Intermediate Similarity	NPD846	Approved
0.8173	Intermediate Similarity	NPD940	Approved
0.8119	Intermediate Similarity	NPD2934	Approved
0.8119	Intermediate Similarity	NPD2933	Approved
0.8039	Intermediate Similarity	NPD1809	Phase 2
0.8037	Intermediate Similarity	NPD1445	Approved
0.8037	Intermediate Similarity	NPD1444	Approved
0.7982	Intermediate Similarity	NPD3021	Approved
0.7982	Intermediate Similarity	NPD3091	Approved
0.7982	Intermediate Similarity	NPD3022	Approved
0.7963	Intermediate Similarity	NPD2342	Discontinued
0.7938	Intermediate Similarity	NPD111	Approved
0.7876	Intermediate Similarity	NPD6671	Approved
0.7818	Intermediate Similarity	NPD1792	Phase 2
0.7788	Intermediate Similarity	NPD9618	Approved
0.7788	Intermediate Similarity	NPD9614	Approved
0.7712	Intermediate Similarity	NPD3092	Approved
0.7603	Intermediate Similarity	NPD3094	Phase 2
0.7586	Intermediate Similarity	NPD9613	Approved
0.7586	Intermediate Similarity	NPD9615	Approved
0.7586	Intermediate Similarity	NPD9616	Approved
0.757	Intermediate Similarity	NPD1242	Phase 1
0.7563	Intermediate Similarity	NPD5350	Clinical (unspecified phase)
0.7563	Intermediate Similarity	NPD5351	Clinical (unspecified phase)
0.7542	Intermediate Similarity	NPD4626	Approved
0.7542	Intermediate Similarity	NPD3095	Discontinued
0.7541	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7522	Intermediate Similarity	NPD228	Approved
0.7522	Intermediate Similarity	NPD6124	Clinical (unspecified phase)
0.7521	Intermediate Similarity	NPD316	Approved
0.7478	Intermediate Similarity	NPD497	Approved
0.7477	Intermediate Similarity	NPD290	Approved
0.7474	Intermediate Similarity	NPD9294	Approved
0.744	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7438	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7438	Intermediate Similarity	NPD4749	Approved
0.7431	Intermediate Similarity	NPD5700	Clinical (unspecified phase)
0.7431	Intermediate Similarity	NPD9500	Approved
0.7411	Intermediate Similarity	NPD2684	Approved
0.7395	Intermediate Similarity	NPD2932	Approved
0.7395	Intermediate Similarity	NPD4059	Approved
0.7395	Intermediate Similarity	NPD1778	Approved
0.7395	Intermediate Similarity	NPD3019	Approved
0.7391	Intermediate Similarity	NPD498	Approved
0.7391	Intermediate Similarity	NPD7159	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD495	Approved
0.7391	Intermediate Similarity	NPD496	Approved
0.7391	Intermediate Similarity	NPD2228	Approved
0.7391	Intermediate Similarity	NPD2234	Approved
0.7391	Intermediate Similarity	NPD2229	Approved
0.7387	Intermediate Similarity	NPD968	Approved
0.7383	Intermediate Similarity	NPD9273	Approved
0.7355	Intermediate Similarity	NPD2232	Approved
0.7355	Intermediate Similarity	NPD2233	Approved
0.7355	Intermediate Similarity	NPD2230	Approved
0.735	Intermediate Similarity	NPD7325	Clinical (unspecified phase)
0.7345	Intermediate Similarity	NPD9380	Clinical (unspecified phase)
0.7339	Intermediate Similarity	NPD2861	Phase 2
0.7333	Intermediate Similarity	NPD3496	Discontinued
0.7328	Intermediate Similarity	NPD1793	Approved
0.7328	Intermediate Similarity	NPD1791	Approved
0.7311	Intermediate Similarity	NPD5691	Approved
0.725	Intermediate Similarity	NPD9384	Approved
0.725	Intermediate Similarity	NPD5238	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD1751	Approved
0.725	Intermediate Similarity	NPD9381	Approved
0.7241	Intermediate Similarity	NPD1398	Phase 1
0.7236	Intermediate Similarity	NPD6696	Suspended
0.7227	Intermediate Similarity	NPD2226	Clinical (unspecified phase)
0.7216	Intermediate Similarity	NPD9088	Approved
0.7213	Intermediate Similarity	NPD2235	Phase 2
0.7213	Intermediate Similarity	NPD2231	Phase 2
0.7207	Intermediate Similarity	NPD9608	Approved
0.7207	Intermediate Similarity	NPD9610	Approved
0.7203	Intermediate Similarity	NPD7340	Approved
0.72	Intermediate Similarity	NPD5736	Approved
0.7179	Intermediate Similarity	NPD1476	Clinical (unspecified phase)
0.7167	Intermediate Similarity	NPD4093	Discontinued
0.7158	Intermediate Similarity	NPD9087	Approved
0.7155	Intermediate Similarity	NPD9379	Approved
0.7155	Intermediate Similarity	NPD9377	Approved
0.7155	Intermediate Similarity	NPD7843	Approved
0.7154	Intermediate Similarity	NPD9622	Approved
0.7143	Intermediate Similarity	NPD600	Approved
0.7143	Intermediate Similarity	NPD16	Approved
0.7143	Intermediate Similarity	NPD596	Approved
0.7143	Intermediate Similarity	NPD856	Approved
0.7131	Intermediate Similarity	NPD1610	Phase 2
0.7131	Intermediate Similarity	NPD1201	Approved
0.7119	Intermediate Similarity	NPD7157	Approved
0.7107	Intermediate Similarity	NPD2286	Discontinued
0.7094	Intermediate Similarity	NPD5283	Phase 1
0.7091	Intermediate Similarity	NPD3028	Approved
0.7087	Intermediate Similarity	NPD4625	Phase 3
0.7087	Intermediate Similarity	NPD3027	Phase 3
0.7083	Intermediate Similarity	NPD5304	Approved
0.7083	Intermediate Similarity	NPD5303	Approved
0.7063	Intermediate Similarity	NPD1712	Approved
0.7059	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7054	Intermediate Similarity	NPD4060	Phase 1
0.7054	Intermediate Similarity	NPD2238	Phase 2
0.7049	Intermediate Similarity	NPD1980	Approved
0.7049	Intermediate Similarity	NPD1981	Approved
0.7049	Intermediate Similarity	NPD1983	Approved
0.704	Intermediate Similarity	NPD1131	Approved
0.704	Intermediate Similarity	NPD1133	Approved
0.704	Intermediate Similarity	NPD1129	Approved
0.704	Intermediate Similarity	NPD1135	Approved
0.704	Intermediate Similarity	NPD1134	Approved
0.7025	Intermediate Similarity	NPD1357	Approved
0.7016	Intermediate Similarity	NPD4659	Approved
0.7009	Intermediate Similarity	NPD1138	Approved
0.7009	Intermediate Similarity	NPD821	Approved
0.7008	Intermediate Similarity	NPD4908	Phase 1
0.7	Intermediate Similarity	NPD318	Approved
0.7	Intermediate Similarity	NPD317	Approved
0.6984	Remote Similarity	NPD602	Approved
0.6984	Remote Similarity	NPD9621	Approved
0.6984	Remote Similarity	NPD6584	Phase 3
0.6984	Remote Similarity	NPD599	Approved
0.6984	Remote Similarity	NPD9620	Approved
0.6984	Remote Similarity	NPD858	Approved
0.6984	Remote Similarity	NPD9619	Approved
0.6984	Remote Similarity	NPD859	Approved
0.6983	Remote Similarity	NPD9280	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD6663	Approved
0.6977	Remote Similarity	NPD840	Approved
0.6977	Remote Similarity	NPD839	Approved
0.6975	Remote Similarity	NPD709	Approved
0.6967	Remote Similarity	NPD4589	Approved
0.696	Remote Similarity	NPD1283	Approved
0.6952	Remote Similarity	NPD9295	Approved
0.6949	Remote Similarity	NPD4869	Clinical (unspecified phase)
0.6947	Remote Similarity	NPD4097	Suspended
0.6942	Remote Similarity	NPD1548	Phase 1
0.6929	Remote Similarity	NPD2237	Approved
0.6923	Remote Similarity	NPD1613	Approved
0.6923	Remote Similarity	NPD3620	Phase 2
0.6923	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD1137	Approved
0.6923	Remote Similarity	NPD1139	Approved
0.6923	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6917	Remote Similarity	NPD9493	Approved
0.6905	Remote Similarity	NPD1470	Approved
0.6899	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6899	Remote Similarity	NPD597	Approved
0.6899	Remote Similarity	NPD598	Approved
0.6899	Remote Similarity	NPD601	Approved
0.6891	Remote Similarity	NPD475	Phase 2
0.6885	Remote Similarity	NPD1651	Approved
0.688	Remote Similarity	NPD1755	Approved
0.6857	Remote Similarity	NPD1101	Approved
0.6855	Remote Similarity	NPD1091	Approved
0.6855	Remote Similarity	NPD1611	Approved
0.685	Remote Similarity	NPD4624	Approved
0.685	Remote Similarity	NPD3690	Phase 2
0.685	Remote Similarity	NPD2194	Approved
0.685	Remote Similarity	NPD2195	Approved
0.685	Remote Similarity	NPD3691	Phase 2
0.6846	Remote Similarity	NPD1136	Approved
0.6846	Remote Similarity	NPD1132	Approved
0.6846	Remote Similarity	NPD1130	Approved
0.6842	Remote Similarity	NPD7742	Approved
0.6842	Remote Similarity	NPD7743	Approved
0.6833	Remote Similarity	NPD255	Approved
0.6833	Remote Similarity	NPD256	Approved
0.6829	Remote Similarity	NPD2667	Approved
0.6829	Remote Similarity	NPD2668	Approved
0.681	Remote Similarity	NPD74	Approved
0.681	Remote Similarity	NPD9266	Approved
0.6803	Remote Similarity	NPD7330	Discontinued
0.6803	Remote Similarity	NPD1759	Phase 1
0.68	Remote Similarity	NPD2561	Approved
0.68	Remote Similarity	NPD2562	Approved
0.6797	Remote Similarity	NPD3636	Approved
0.6797	Remote Similarity	NPD3637	Approved
0.6797	Remote Similarity	NPD3635	Approved
0.6794	Remote Similarity	NPD4140	Approved
0.6792	Remote Similarity	NPD800	Approved
0.6786	Remote Similarity	NPD1616	Discontinued
0.6783	Remote Similarity	NPD3134	Approved
0.6774	Remote Similarity	NPD3023	Approved
0.6774	Remote Similarity	NPD3026	Approved
0.6772	Remote Similarity	NPD4103	Phase 2
0.6772	Remote Similarity	NPD4104	Clinical (unspecified phase)
0.6772	Remote Similarity	NPD4339	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD5177	Phase 3
0.6765	Remote Similarity	NPD5698	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD9089	Approved
0.6757	Remote Similarity	NPD9609	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