NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	212.1
Volume:	217.507
LogP:	0.33
LogD:	0.621
LogS:	-0.995
# Rotatable Bonds:	3
TPSA:	80.92
# H-Bond Aceptor:	4
# H-Bond Donor:	4
# Rings:	1
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.558
Synthetic Accessibility Score:	2.944
Fsp3:	0.455
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.621
MDCK Permeability:	1.2443199921108317e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.051
Human Intestinal Absorption (HIA):	0.017
20% Bioavailability (F20%):	0.944
30% Bioavailability (F30%):	0.15

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.058
Plasma Protein Binding (PPB):	40.29931640625%
Volume Distribution (VD):	1.877
Pgp-substrate:	62.51041793823242%

ADMET: Metabolism

CYP1A2-inhibitor:	0.051
CYP1A2-substrate:	0.099
CYP2C19-inhibitor:	0.025
CYP2C19-substrate:	0.114
CYP2C9-inhibitor:	0.015
CYP2C9-substrate:	0.86
CYP2D6-inhibitor:	0.038
CYP2D6-substrate:	0.548
CYP3A4-inhibitor:	0.013
CYP3A4-substrate:	0.162

ADMET: Excretion

Clearance (CL):	14.102
Half-life (T1/2):	0.904

ADMET: Toxicity

hERG Blockers:	0.022
Human Hepatotoxicity (H-HT):	0.056
Drug-inuced Liver Injury (DILI):	0.036
AMES Toxicity:	0.053
Rat Oral Acute Toxicity:	0.41
Maximum Recommended Daily Dose:	0.067
Skin Sensitization:	0.744
Carcinogencity:	0.07
Eye Corrosion:	0.074
Eye Irritation:	0.91
Respiratory Toxicity:	0.033

Download Data

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

Natural Product: NPC473524

Natural Product ID:	NPC473524
*Common Name:**	2-(2,3-Dihydroxy-3-Methylbutyl)Benzene-1,4-Diol
IUPAC Name:	2-(2,3-dihydroxy-3-methylbutyl)benzene-1,4-diol
Synonyms:
Standard InCHIKey:	VYXPSMUFCGRWJC-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C11H16O4/c1-11(2,15)10(14)6-7-5-8(12)3-4-9(7)13/h3-5,10,12-15H,6H2,1-2H3
SMILES:	Oc1ccc(c(c1)CC(C(O)(C)C)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL444672
PubChem CID:	9837238
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001534] Quinone and hydroquinone lipids [CHEMONTID:0002801] Prenylated hydroquinones

*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	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO32963	Acremonium sp.	Species	Eukaryota	n.a.	n.a.	n.a.	PMID[12444684]
NPO32963	Acremonium sp.	Species	Eukaryota	n.a.	n.a.	n.a.	PMID[16441074]
NPO32963	Acremonium sp.	Species	Eukaryota	n.a.	Australian	n.a.	PMID[18288804]
NPO32963	Acremonium sp.	Species	Eukaryota	n.a.	n.a.	n.a.	PMID[19199645]
NPO32963	Acremonium sp.	Species	Eukaryota	n.a.	Mangrove Rhizophora apiculata	n.a.	PMID[22524636]
NPO32963	Acremonium sp.	Species	Eukaryota	n.a.	n.a.	n.a.	PMID[22524636]
NPO32963	Acremonium sp.	Species	Eukaryota	n.a.	n.a.	n.a.	PMID[25689430]
NPO32963	Acremonium sp.	Species	Eukaryota	n.a.	n.a.	n.a.	PMID[26928174]

☑ 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	6

Activity Type	# Activity
NON-MOLECULAR	2
Others	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	=	2.0	%	PMID[547748]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	16.6	%	PMID[547748]
NPT1	Others	Radical scavenging activity		Activity	=	90.2	%	PMID[547748]
NPT1	Others	Radical scavenging activity		Activity	=	90.7	%	PMID[547748]
NPT1	Others	Radical scavenging activity		Activity	=	89.9	%	PMID[547748]
NPT1	Others	Radical scavenging activity		Activity	=	82.9	%	PMID[547748]

☑ 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 NPC473524 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	252
0.1-0.2	1336
0.2-0.3	4196
0.3-0.4	12453
0.4-0.5	7228
0.5-0.6	9089
0.6-0.7	6262
0.7-0.8	1662
0.8-0.85	166
0.85-0.9	45
0.9-0.95	7
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9266	High Similarity	NPC320864
0.9208	High Similarity	NPC130103
0.9048	High Similarity	NPC474352
0.901	High Similarity	NPC474073
0.8846	High Similarity	NPC471228
0.8846	High Similarity	NPC235762
0.8846	High Similarity	NPC108497
0.8835	High Similarity	NPC174911
0.8835	High Similarity	NPC48730
0.8835	High Similarity	NPC129373
0.8835	High Similarity	NPC248396
0.8824	High Similarity	NPC152097
0.8824	High Similarity	NPC475078
0.8774	High Similarity	NPC469913
0.8762	High Similarity	NPC475225
0.8738	High Similarity	NPC260775
0.8716	High Similarity	NPC54373
0.8692	High Similarity	NPC66834
0.8684	High Similarity	NPC223451
0.8679	High Similarity	NPC471350
0.8673	High Similarity	NPC206205
0.8654	High Similarity	NPC70677
0.8654	High Similarity	NPC130756
0.8654	High Similarity	NPC12931
0.8649	High Similarity	NPC12656
0.8641	High Similarity	NPC88420
0.8614	High Similarity	NPC29373
0.8609	High Similarity	NPC473875
0.8598	High Similarity	NPC53740
0.8596	High Similarity	NPC476020
0.8571	High Similarity	NPC80800
0.8571	High Similarity	NPC474486
0.8571	High Similarity	NPC232165
0.8571	High Similarity	NPC477685
0.8519	High Similarity	NPC305603
0.8519	High Similarity	NPC61033
0.8505	High Similarity	NPC47284
0.8491	Intermediate Similarity	NPC269212
0.8482	Intermediate Similarity	NPC474050
0.8482	Intermediate Similarity	NPC473137
0.8482	Intermediate Similarity	NPC473931
0.8482	Intermediate Similarity	NPC474114
0.8476	Intermediate Similarity	NPC294741
0.8476	Intermediate Similarity	NPC72729
0.8468	Intermediate Similarity	NPC302371
0.8455	Intermediate Similarity	NPC471535
0.8448	Intermediate Similarity	NPC475529
0.8447	Intermediate Similarity	NPC313650
0.8426	Intermediate Similarity	NPC155072
0.8416	Intermediate Similarity	NPC312304
0.8411	Intermediate Similarity	NPC12278
0.8411	Intermediate Similarity	NPC475580
0.8411	Intermediate Similarity	NPC130817
0.8411	Intermediate Similarity	NPC323810
0.8403	Intermediate Similarity	NPC33654
0.8396	Intermediate Similarity	NPC12221
0.8396	Intermediate Similarity	NPC471578
0.8396	Intermediate Similarity	NPC101025
0.8393	Intermediate Similarity	NPC28784
0.8393	Intermediate Similarity	NPC261343
0.8393	Intermediate Similarity	NPC296144
0.8381	Intermediate Similarity	NPC128723
0.8378	Intermediate Similarity	NPC469912
0.8378	Intermediate Similarity	NPC308689
0.8364	Intermediate Similarity	NPC98392
0.8349	Intermediate Similarity	NPC320439
0.8349	Intermediate Similarity	NPC233320
0.8319	Intermediate Similarity	NPC197513
0.8319	Intermediate Similarity	NPC120280
0.8305	Intermediate Similarity	NPC46586
0.8305	Intermediate Similarity	NPC204535
0.8304	Intermediate Similarity	NPC473521
0.8304	Intermediate Similarity	NPC228452
0.8288	Intermediate Similarity	NPC120982
0.8288	Intermediate Similarity	NPC226401
0.8288	Intermediate Similarity	NPC174096
0.8288	Intermediate Similarity	NPC147634
0.8288	Intermediate Similarity	NPC79793
0.8288	Intermediate Similarity	NPC44732
0.8286	Intermediate Similarity	NPC79241
0.8286	Intermediate Similarity	NPC6597
0.8279	Intermediate Similarity	NPC158477
0.8276	Intermediate Similarity	NPC121866
0.8273	Intermediate Similarity	NPC306295
0.8273	Intermediate Similarity	NPC95344
0.8252	Intermediate Similarity	NPC138117
0.8252	Intermediate Similarity	NPC325292
0.8252	Intermediate Similarity	NPC94139
0.8252	Intermediate Similarity	NPC306884
0.8252	Intermediate Similarity	NPC162314
0.8252	Intermediate Similarity	NPC210497
0.8252	Intermediate Similarity	NPC147284
0.8252	Intermediate Similarity	NPC3358
0.8241	Intermediate Similarity	NPC272029
0.8241	Intermediate Similarity	NPC244513
0.8241	Intermediate Similarity	NPC218879
0.8241	Intermediate Similarity	NPC227458
0.8235	Intermediate Similarity	NPC192
0.8235	Intermediate Similarity	NPC474130
0.823	Intermediate Similarity	NPC319803
0.823	Intermediate Similarity	NPC471485
0.8224	Intermediate Similarity	NPC110764
0.8218	Intermediate Similarity	NPC27974
0.8214	Intermediate Similarity	NPC179002
0.8214	Intermediate Similarity	NPC187583
0.8214	Intermediate Similarity	NPC275627
0.8214	Intermediate Similarity	NPC257430
0.8208	Intermediate Similarity	NPC33675
0.8208	Intermediate Similarity	NPC299762
0.8198	Intermediate Similarity	NPC62258
0.8198	Intermediate Similarity	NPC55617
0.819	Intermediate Similarity	NPC312132
0.819	Intermediate Similarity	NPC259512
0.819	Intermediate Similarity	NPC283616
0.819	Intermediate Similarity	NPC48781
0.819	Intermediate Similarity	NPC9592
0.8182	Intermediate Similarity	NPC204901
0.8182	Intermediate Similarity	NPC474945
0.8182	Intermediate Similarity	NPC476022
0.8182	Intermediate Similarity	NPC158253
0.8182	Intermediate Similarity	NPC232523
0.8174	Intermediate Similarity	NPC154256
0.8174	Intermediate Similarity	NPC141001
0.8174	Intermediate Similarity	NPC290470
0.8173	Intermediate Similarity	NPC245187
0.8173	Intermediate Similarity	NPC152415
0.8165	Intermediate Similarity	NPC37802
0.8158	Intermediate Similarity	NPC471534
0.8155	Intermediate Similarity	NPC231150
0.8148	Intermediate Similarity	NPC222522
0.8148	Intermediate Similarity	NPC233827
0.8148	Intermediate Similarity	NPC249828
0.8148	Intermediate Similarity	NPC85479
0.8148	Intermediate Similarity	NPC71002
0.8148	Intermediate Similarity	NPC94351
0.8148	Intermediate Similarity	NPC53051
0.8148	Intermediate Similarity	NPC24404
0.8148	Intermediate Similarity	NPC146798
0.8148	Intermediate Similarity	NPC302219
0.8148	Intermediate Similarity	NPC106396
0.8148	Intermediate Similarity	NPC242342
0.8148	Intermediate Similarity	NPC168303
0.8148	Intermediate Similarity	NPC313030
0.8131	Intermediate Similarity	NPC10588
0.8131	Intermediate Similarity	NPC166761
0.8125	Intermediate Similarity	NPC475018
0.8125	Intermediate Similarity	NPC208229
0.8125	Intermediate Similarity	NPC132720
0.812	Intermediate Similarity	NPC323074
0.812	Intermediate Similarity	NPC160235
0.8119	Intermediate Similarity	NPC407
0.8119	Intermediate Similarity	NPC307235
0.8108	Intermediate Similarity	NPC68260
0.8108	Intermediate Similarity	NPC262365
0.8108	Intermediate Similarity	NPC174981
0.8108	Intermediate Similarity	NPC279887
0.8108	Intermediate Similarity	NPC241549
0.8108	Intermediate Similarity	NPC169450
0.8091	Intermediate Similarity	NPC201662
0.8091	Intermediate Similarity	NPC99836
0.8091	Intermediate Similarity	NPC310456
0.8091	Intermediate Similarity	NPC12640
0.8091	Intermediate Similarity	NPC54765
0.8077	Intermediate Similarity	NPC55903
0.8073	Intermediate Similarity	NPC102216
0.8073	Intermediate Similarity	NPC93831
0.8067	Intermediate Similarity	NPC476343
0.8058	Intermediate Similarity	NPC300478
0.8058	Intermediate Similarity	NPC300017
0.8058	Intermediate Similarity	NPC47950
0.8056	Intermediate Similarity	NPC284011
0.8056	Intermediate Similarity	NPC91461
0.8056	Intermediate Similarity	NPC11280
0.8056	Intermediate Similarity	NPC192032
0.8056	Intermediate Similarity	NPC24407
0.8056	Intermediate Similarity	NPC7686
0.8056	Intermediate Similarity	NPC147310
0.8056	Intermediate Similarity	NPC252105
0.8056	Intermediate Similarity	NPC72947
0.8056	Intermediate Similarity	NPC166313
0.8056	Intermediate Similarity	NPC294186
0.8056	Intermediate Similarity	NPC137415
0.8056	Intermediate Similarity	NPC40258
0.8053	Intermediate Similarity	NPC77772
0.8053	Intermediate Similarity	NPC266937
0.8053	Intermediate Similarity	NPC228609
0.8053	Intermediate Similarity	NPC470770
0.8051	Intermediate Similarity	NPC477037
0.8051	Intermediate Similarity	NPC472071
0.8051	Intermediate Similarity	NPC325544
0.8051	Intermediate Similarity	NPC318581
0.8051	Intermediate Similarity	NPC232295
0.8037	Intermediate Similarity	NPC51333
0.8037	Intermediate Similarity	NPC78119
0.8037	Intermediate Similarity	NPC132078
0.8037	Intermediate Similarity	NPC216468
0.8037	Intermediate Similarity	NPC131587
0.8036	Intermediate Similarity	NPC33728
0.8036	Intermediate Similarity	NPC19808
0.8036	Intermediate Similarity	NPC282855

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 NPC473524 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	248
0.1-0.2	863
0.2-0.3	1742
0.3-0.4	2945
0.4-0.5	1722
0.5-0.6	1135
0.6-0.7	423
0.7-0.8	69
0.8-0.85	2
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8654	High Similarity	NPD289	Clinical (unspecified phase)
0.8447	Intermediate Similarity	NPD844	Approved
0.819	Intermediate Similarity	NPD288	Approved
0.8056	Intermediate Similarity	NPD940	Approved
0.8056	Intermediate Similarity	NPD846	Approved
0.7931	Intermediate Similarity	NPD6671	Approved
0.7905	Intermediate Similarity	NPD845	Approved
0.7876	Intermediate Similarity	NPD4750	Phase 3
0.7876	Intermediate Similarity	NPD3021	Approved
0.7876	Intermediate Similarity	NPD3022	Approved
0.783	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.7826	Intermediate Similarity	NPD7635	Approved
0.7757	Intermediate Similarity	NPD2859	Approved
0.7757	Intermediate Similarity	NPD2860	Approved
0.7706	Intermediate Similarity	NPD3020	Approved
0.7664	Intermediate Similarity	NPD2934	Approved
0.7664	Intermediate Similarity	NPD2933	Approved
0.7661	Intermediate Similarity	NPD3094	Phase 2
0.7623	Intermediate Similarity	NPD3092	Approved
0.7603	Intermediate Similarity	NPD9381	Approved
0.7603	Intermediate Similarity	NPD9384	Approved
0.7593	Intermediate Similarity	NPD1809	Phase 2
0.7559	Intermediate Similarity	NPD3027	Phase 3
0.7544	Intermediate Similarity	NPD290	Approved
0.7542	Intermediate Similarity	NPD9614	Approved
0.7542	Intermediate Similarity	NPD9618	Approved
0.754	Intermediate Similarity	NPD2861	Phase 2
0.75	Intermediate Similarity	NPD9622	Approved
0.7477	Intermediate Similarity	NPD1242	Phase 1
0.7476	Intermediate Similarity	NPD111	Approved
0.7456	Intermediate Similarity	NPD1445	Approved
0.7456	Intermediate Similarity	NPD1444	Approved
0.7438	Intermediate Similarity	NPD3091	Approved
0.7436	Intermediate Similarity	NPD228	Approved
0.7414	Intermediate Similarity	NPD9380	Clinical (unspecified phase)
0.7398	Intermediate Similarity	NPD3496	Discontinued
0.7385	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7385	Intermediate Similarity	NPD1613	Approved
0.7355	Intermediate Similarity	NPD9616	Approved
0.7355	Intermediate Similarity	NPD9615	Approved
0.7355	Intermediate Similarity	NPD9613	Approved
0.735	Intermediate Similarity	NPD9280	Clinical (unspecified phase)
0.7339	Intermediate Similarity	NPD1091	Approved
0.7328	Intermediate Similarity	NPD2684	Approved
0.7323	Intermediate Similarity	NPD9619	Approved
0.7323	Intermediate Similarity	NPD9621	Approved
0.7323	Intermediate Similarity	NPD9620	Approved
0.7311	Intermediate Similarity	NPD7159	Clinical (unspecified phase)
0.7304	Intermediate Similarity	NPD968	Approved
0.7302	Intermediate Similarity	NPD6696	Suspended
0.7295	Intermediate Similarity	NPD316	Approved
0.7288	Intermediate Similarity	NPD6124	Clinical (unspecified phase)
0.7265	Intermediate Similarity	NPD1792	Phase 2
0.725	Intermediate Similarity	NPD497	Approved
0.7241	Intermediate Similarity	NPD2342	Discontinued
0.7231	Intermediate Similarity	NPD601	Approved
0.7231	Intermediate Similarity	NPD598	Approved
0.7231	Intermediate Similarity	NPD597	Approved
0.7227	Intermediate Similarity	NPD7843	Approved
0.7213	Intermediate Similarity	NPD16	Approved
0.7213	Intermediate Similarity	NPD856	Approved
0.7209	Intermediate Similarity	NPD600	Approved
0.7209	Intermediate Similarity	NPD596	Approved
0.72	Intermediate Similarity	NPD5350	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD5351	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD7157	Approved
0.7177	Intermediate Similarity	NPD3095	Discontinued
0.7177	Intermediate Similarity	NPD5238	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD840	Approved
0.7176	Intermediate Similarity	NPD1130	Approved
0.7176	Intermediate Similarity	NPD1136	Approved
0.7176	Intermediate Similarity	NPD839	Approved
0.7176	Intermediate Similarity	NPD1132	Approved
0.7167	Intermediate Similarity	NPD496	Approved
0.7167	Intermediate Similarity	NPD495	Approved
0.7167	Intermediate Similarity	NPD498	Approved
0.7129	Intermediate Similarity	NPD9088	Approved
0.7121	Intermediate Similarity	NPD3062	Approved
0.7121	Intermediate Similarity	NPD2238	Phase 2
0.7121	Intermediate Similarity	NPD3059	Approved
0.7121	Intermediate Similarity	NPD3061	Approved
0.7109	Intermediate Similarity	NPD1129	Approved
0.7109	Intermediate Similarity	NPD1133	Approved
0.7109	Intermediate Similarity	NPD1134	Approved
0.7109	Intermediate Similarity	NPD1131	Approved
0.7109	Intermediate Similarity	NPD1135	Approved
0.7099	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7087	Intermediate Similarity	NPD4749	Approved
0.7087	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD9379	Approved
0.7083	Intermediate Similarity	NPD9377	Approved
0.7077	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD317	Approved
0.7073	Intermediate Similarity	NPD318	Approved
0.7054	Intermediate Similarity	NPD858	Approved
0.7054	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7054	Intermediate Similarity	NPD599	Approved
0.7054	Intermediate Similarity	NPD602	Approved
0.7054	Intermediate Similarity	NPD859	Approved
0.7043	Intermediate Similarity	NPD9500	Approved
0.703	Intermediate Similarity	NPD9294	Approved
0.7025	Intermediate Similarity	NPD2234	Approved
0.7025	Intermediate Similarity	NPD2229	Approved
0.7025	Intermediate Similarity	NPD2228	Approved
0.7025	Intermediate Similarity	NPD1398	Phase 1
0.7015	Intermediate Similarity	NPD817	Approved
0.7015	Intermediate Similarity	NPD5314	Approved
0.7015	Intermediate Similarity	NPD823	Approved
0.7008	Intermediate Similarity	NPD2230	Approved
0.7008	Intermediate Similarity	NPD2233	Approved
0.7008	Intermediate Similarity	NPD2232	Approved
0.7	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.6992	Remote Similarity	NPD4060	Phase 1
0.6991	Remote Similarity	NPD9273	Approved
0.6977	Remote Similarity	NPD4339	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD4104	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD4103	Phase 2
0.6967	Remote Similarity	NPD1476	Clinical (unspecified phase)
0.6967	Remote Similarity	NPD1791	Approved
0.6967	Remote Similarity	NPD1793	Approved
0.696	Remote Similarity	NPD1357	Approved
0.6957	Remote Similarity	NPD5698	Clinical (unspecified phase)
0.6953	Remote Similarity	NPD4659	Approved
0.6947	Remote Similarity	NPD4908	Phase 1
0.6934	Remote Similarity	NPD2029	Clinical (unspecified phase)
0.6934	Remote Similarity	NPD5763	Approved
0.6934	Remote Similarity	NPD7266	Discontinued
0.6934	Remote Similarity	NPD5762	Approved
0.6929	Remote Similarity	NPD1610	Phase 2
0.6929	Remote Similarity	NPD1201	Approved
0.6917	Remote Similarity	NPD6405	Approved
0.6917	Remote Similarity	NPD6407	Approved
0.6905	Remote Similarity	NPD1778	Approved
0.6905	Remote Similarity	NPD4626	Approved
0.6905	Remote Similarity	NPD4059	Approved
0.6899	Remote Similarity	NPD8651	Approved
0.6894	Remote Similarity	NPD4625	Phase 3
0.6889	Remote Similarity	NPD2568	Approved
0.6885	Remote Similarity	NPD4869	Clinical (unspecified phase)
0.6885	Remote Similarity	NPD5283	Phase 1
0.6881	Remote Similarity	NPD9295	Approved
0.688	Remote Similarity	NPD1548	Phase 1
0.688	Remote Similarity	NPD2226	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD2561	Approved
0.6875	Remote Similarity	NPD2562	Approved
0.6875	Remote Similarity	NPD2231	Phase 2
0.6875	Remote Similarity	NPD2235	Phase 2
0.687	Remote Similarity	NPD3028	Approved
0.6855	Remote Similarity	NPD7340	Approved
0.6846	Remote Similarity	NPD1470	Approved
0.6842	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD9495	Approved
0.6838	Remote Similarity	NPD9610	Approved
0.6838	Remote Similarity	NPD9608	Approved
0.6772	Remote Similarity	NPD2932	Approved
0.6772	Remote Similarity	NPD3019	Approved
0.6765	Remote Similarity	NPD6653	Approved
0.6752	Remote Similarity	NPD5700	Clinical (unspecified phase)
0.6742	Remote Similarity	NPD5736	Approved
0.6741	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6741	Remote Similarity	NPD826	Approved
0.6741	Remote Similarity	NPD943	Approved
0.6741	Remote Similarity	NPD825	Approved
0.6741	Remote Similarity	NPD3620	Phase 2
0.6739	Remote Similarity	NPD9570	Approved
0.6739	Remote Similarity	NPD2935	Discontinued
0.6738	Remote Similarity	NPD6190	Approved
0.6738	Remote Similarity	NPD2677	Approved
0.6733	Remote Similarity	NPD9087	Approved
0.672	Remote Similarity	NPD405	Clinical (unspecified phase)
0.672	Remote Similarity	NPD7325	Clinical (unspecified phase)
0.6715	Remote Similarity	NPD4536	Approved
0.6715	Remote Similarity	NPD4537	Clinical (unspecified phase)
0.6715	Remote Similarity	NPD4538	Approved
0.6698	Remote Similarity	NPD9089	Approved
0.6694	Remote Similarity	NPD2629	Approved
0.6693	Remote Similarity	NPD4093	Discontinued
0.6693	Remote Similarity	NPD5691	Approved
0.6692	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6691	Remote Similarity	NPD5735	Approved
0.669	Remote Similarity	NPD1653	Approved
0.6667	Remote Similarity	NPD7033	Discontinued
0.6667	Remote Similarity	NPD821	Approved
0.6667	Remote Similarity	NPD558	Phase 2
0.6667	Remote Similarity	NPD1138	Approved
0.6667	Remote Similarity	NPD6584	Phase 3
0.6667	Remote Similarity	NPD258	Approved
0.6667	Remote Similarity	NPD1611	Approved
0.6667	Remote Similarity	NPD257	Approved
0.6667	Remote Similarity	NPD3705	Approved
0.6643	Remote Similarity	NPD2424	Discontinued
0.6641	Remote Similarity	NPD9634	Clinical (unspecified phase)
0.6641	Remote Similarity	NPD5126	Approved
0.6641	Remote Similarity	NPD5125	Phase 3
0.6641	Remote Similarity	NPD4589	Approved
0.6641	Remote Similarity	NPD1751	Approved
0.664	Remote Similarity	NPD709	Approved
0.6636	Remote Similarity	NPD9094	Approved
0.6619	Remote Similarity	NPD6032	Approved
0.6617	Remote Similarity	NPD1712	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