NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	192.12
Volume:	214.586
LogP:	3.709
LogD:	3.234
LogS:	-3.271
# Rotatable Bonds:	3
TPSA:	29.46
# H-Bond Aceptor:	2
# H-Bond Donor:	1
# Rings:	1
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.746
Synthetic Accessibility Score:	2.079
Fsp3:	0.333
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.496
MDCK Permeability:	2.1915850084042177e-05
Pgp-inhibitor:	0.018
Pgp-substrate:	0.005
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.935
30% Bioavailability (F30%):	0.462

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.256
Plasma Protein Binding (PPB):	96.16931915283203%
Volume Distribution (VD):	4.396
Pgp-substrate:	6.379258632659912%

ADMET: Metabolism

CYP1A2-inhibitor:	0.97
CYP1A2-substrate:	0.9
CYP2C19-inhibitor:	0.921
CYP2C19-substrate:	0.641
CYP2C9-inhibitor:	0.504
CYP2C9-substrate:	0.938
CYP2D6-inhibitor:	0.846
CYP2D6-substrate:	0.906
CYP3A4-inhibitor:	0.252
CYP3A4-substrate:	0.273

ADMET: Excretion

Clearance (CL):	16.02
Half-life (T1/2):	0.74

ADMET: Toxicity

hERG Blockers:	0.022
Human Hepatotoxicity (H-HT):	0.442
Drug-inuced Liver Injury (DILI):	0.091
AMES Toxicity:	0.037
Rat Oral Acute Toxicity:	0.039
Maximum Recommended Daily Dose:	0.121
Skin Sensitization:	0.793
Carcinogencity:	0.174
Eye Corrosion:	0.528
Eye Irritation:	0.982
Respiratory Toxicity:	0.271

Download Data

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

Natural Product: NPC233320

Natural Product ID:	NPC233320
*Common Name:**	4-Methoxy-2-(3-Methylbut-2-Enyl)Phenol
IUPAC Name:	4-methoxy-2-(3-methylbut-2-enyl)phenol
Synonyms:
Standard InCHIKey:	GKAOOQRLNNPWFH-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C12H16O2/c1-9(2)4-5-10-8-11(14-3)6-7-12(10)13/h4,6-8,13H,5H2,1-3H3
SMILES:	COc1ccc(c(c1)CC=C(C)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL508246
PubChem CID:	11819902
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000134] Phenols [CHEMONTID:0000190] Methoxyphenols

*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
NPO32602	lactarius lignyotus	Species	Russulaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7673933]
NPO3916	Stenotrophomonas maltophilia	Species	Xanthomonadaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO4481	Eutrema salsugineum	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22784	Umbellularia californica	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23587	Astragalus ciceroides	Species	Fabaceae	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
Others	24

Activity Type	# Activity
Cell Line	12
CELL-LINE	12

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT116	Cell Line	HL-60	Homo sapiens	Activity	=	64.0	%	PMID[491162]
NPT116	Cell Line	HL-60	Homo sapiens	Activity	=	32.0	%	PMID[491162]
NPT116	Cell Line	HL-60	Homo sapiens	Activity	=	14.0	%	PMID[491162]
NPT116	Cell Line	HL-60	Homo sapiens	Activity	=	1.5	%	PMID[491162]
NPT116	Cell Line	HL-60	Homo sapiens	Activity	=	49.0	%	PMID[491162]
NPT116	Cell Line	HL-60	Homo sapiens	Activity	=	38.0	%	PMID[491162]
NPT116	Cell Line	HL-60	Homo sapiens	Activity	=	35.0	%	PMID[491162]
NPT116	Cell Line	HL-60	Homo sapiens	Activity	=	98.0	%	PMID[491162]
NPT116	Cell Line	HL-60	Homo sapiens	Activity	=	50.0	%	PMID[491162]
NPT116	Cell Line	HL-60	Homo sapiens	Activity	=	55.0	%	PMID[491162]
NPT20987	CELL-LINE	HeLa S3	Homo sapiens	Activity	=	100.0	%	PMID[491162]
NPT20987	CELL-LINE	HeLa S3	Homo sapiens	Activity	=	59.0	%	PMID[491162]
NPT20987	CELL-LINE	HeLa S3	Homo sapiens	Activity	=	70.0	%	PMID[491162]
NPT20987	CELL-LINE	HeLa S3	Homo sapiens	Activity	=	31.0	%	PMID[491162]
NPT20987	CELL-LINE	HeLa S3	Homo sapiens	Activity	=	96.0	%	PMID[491162]
NPT20987	CELL-LINE	HeLa S3	Homo sapiens	Activity	=	43.0	%	PMID[491162]
NPT20987	CELL-LINE	HeLa S3	Homo sapiens	Activity	=	38.0	%	PMID[491162]
NPT20987	CELL-LINE	HeLa S3	Homo sapiens	Activity	=	37.0	%	PMID[491162]
NPT20987	CELL-LINE	HeLa S3	Homo sapiens	Activity	=	97.0	%	PMID[491162]
NPT20987	CELL-LINE	HeLa S3	Homo sapiens	Activity	=	86.0	%	PMID[491162]
NPT20987	CELL-LINE	HeLa S3	Homo sapiens	Activity	=	91.0	%	PMID[491162]
NPT20987	CELL-LINE	HeLa S3	Homo sapiens	Activity	=	90.0	%	PMID[491162]

☑ 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 NPC233320 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	262
0.1-0.2	1903
0.2-0.3	6103
0.3-0.4	13086
0.4-0.5	4194
0.5-0.6	7519
0.6-0.7	7126
0.7-0.8	2181
0.8-0.85	249
0.85-0.9	67
0.9-0.95	4
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9612	High Similarity	NPC275627
0.9333	High Similarity	NPC98372
0.932	High Similarity	NPC241549
0.9151	High Similarity	NPC474920
0.9118	High Similarity	NPC130817
0.9	High Similarity	NPC152097
0.8952	High Similarity	NPC75440
0.8942	High Similarity	NPC30416
0.8911	High Similarity	NPC260775
0.8899	High Similarity	NPC473718
0.8879	High Similarity	NPC195873
0.8829	High Similarity	NPC283616
0.8824	High Similarity	NPC70677
0.8824	High Similarity	NPC12931
0.8824	High Similarity	NPC130756
0.8824	High Similarity	NPC129373
0.8824	High Similarity	NPC248396
0.8824	High Similarity	NPC48730
0.8818	High Similarity	NPC69539
0.8818	High Similarity	NPC290470
0.8818	High Similarity	NPC154256
0.8812	High Similarity	NPC475078
0.8807	High Similarity	NPC470837
0.8788	High Similarity	NPC29373
0.8761	High Similarity	NPC129176
0.875	High Similarity	NPC474603
0.875	High Similarity	NPC471449
0.875	High Similarity	NPC51341
0.875	High Similarity	NPC12987
0.875	High Similarity	NPC32152
0.8739	High Similarity	NPC238176
0.8739	High Similarity	NPC187993
0.8727	High Similarity	NPC301321
0.8727	High Similarity	NPC808
0.8673	High Similarity	NPC232295
0.8673	High Similarity	NPC474131
0.8654	High Similarity	NPC108497
0.8654	High Similarity	NPC24327
0.8654	High Similarity	NPC12870
0.8649	High Similarity	NPC150624
0.8641	High Similarity	NPC130103
0.8627	High Similarity	NPC470161
0.8611	High Similarity	NPC168657
0.8609	High Similarity	NPC474864
0.8598	High Similarity	NPC169450
0.8596	High Similarity	NPC475529
0.8596	High Similarity	NPC277798
0.8596	High Similarity	NPC473875
0.8596	High Similarity	NPC100108
0.8585	High Similarity	NPC113457
0.8571	High Similarity	NPC33270
0.8571	High Similarity	NPC69261
0.8559	High Similarity	NPC232165
0.8558	High Similarity	NPC80800
0.8558	High Similarity	NPC477685
0.8545	High Similarity	NPC141003
0.8545	High Similarity	NPC35344
0.8544	High Similarity	NPC100870
0.8532	High Similarity	NPC173746
0.8532	High Similarity	NPC156840
0.8532	High Similarity	NPC8547
0.8532	High Similarity	NPC257124
0.8522	High Similarity	NPC476165
0.8522	High Similarity	NPC285289
0.8496	Intermediate Similarity	NPC190514
0.8491	Intermediate Similarity	NPC47284
0.8476	Intermediate Similarity	NPC235762
0.8476	Intermediate Similarity	NPC471228
0.8476	Intermediate Similarity	NPC269212
0.8468	Intermediate Similarity	NPC22610
0.8468	Intermediate Similarity	NPC276737
0.8462	Intermediate Similarity	NPC174911
0.8455	Intermediate Similarity	NPC228452
0.8448	Intermediate Similarity	NPC46586
0.8448	Intermediate Similarity	NPC204535
0.8448	Intermediate Similarity	NPC246967
0.8448	Intermediate Similarity	NPC135414
0.8448	Intermediate Similarity	NPC49441
0.8447	Intermediate Similarity	NPC474073
0.8447	Intermediate Similarity	NPC88420
0.844	Intermediate Similarity	NPC137685
0.8435	Intermediate Similarity	NPC45663
0.8435	Intermediate Similarity	NPC96423
0.8426	Intermediate Similarity	NPC201959
0.8421	Intermediate Similarity	NPC184302
0.8411	Intermediate Similarity	NPC164576
0.8411	Intermediate Similarity	NPC155072
0.8411	Intermediate Similarity	NPC53740
0.8407	Intermediate Similarity	NPC50521
0.8407	Intermediate Similarity	NPC244816
0.8407	Intermediate Similarity	NPC221549
0.8396	Intermediate Similarity	NPC475225
0.8396	Intermediate Similarity	NPC108875
0.8396	Intermediate Similarity	NPC38079
0.8396	Intermediate Similarity	NPC475580
0.8393	Intermediate Similarity	NPC53906
0.8393	Intermediate Similarity	NPC283169
0.8384	Intermediate Similarity	NPC157213
0.8384	Intermediate Similarity	NPC27974
0.8381	Intermediate Similarity	NPC12221
0.8376	Intermediate Similarity	NPC474130
0.8364	Intermediate Similarity	NPC54373
0.8362	Intermediate Similarity	NPC48623
0.8362	Intermediate Similarity	NPC168707
0.8349	Intermediate Similarity	NPC233731
0.8349	Intermediate Similarity	NPC7097
0.8349	Intermediate Similarity	NPC246358
0.8349	Intermediate Similarity	NPC473524
0.8349	Intermediate Similarity	NPC98392
0.8349	Intermediate Similarity	NPC36108
0.8348	Intermediate Similarity	NPC14177
0.8333	Intermediate Similarity	NPC474352
0.8333	Intermediate Similarity	NPC320439
0.8333	Intermediate Similarity	NPC245187
0.8333	Intermediate Similarity	NPC329980
0.8333	Intermediate Similarity	NPC63010
0.8319	Intermediate Similarity	NPC112596
0.8319	Intermediate Similarity	NPC141090
0.8319	Intermediate Similarity	NPC203113
0.8319	Intermediate Similarity	NPC163398
0.8318	Intermediate Similarity	NPC227255
0.8318	Intermediate Similarity	NPC470393
0.8318	Intermediate Similarity	NPC288760
0.8317	Intermediate Similarity	NPC231150
0.8317	Intermediate Similarity	NPC321956
0.8305	Intermediate Similarity	NPC147896
0.8305	Intermediate Similarity	NPC276962
0.8305	Intermediate Similarity	NPC248557
0.8305	Intermediate Similarity	NPC61685
0.8305	Intermediate Similarity	NPC190086
0.8305	Intermediate Similarity	NPC183446
0.8302	Intermediate Similarity	NPC233827
0.8302	Intermediate Similarity	NPC305205
0.8291	Intermediate Similarity	NPC77789
0.8291	Intermediate Similarity	NPC302211
0.8291	Intermediate Similarity	NPC18128
0.8288	Intermediate Similarity	NPC26615
0.8286	Intermediate Similarity	NPC72729
0.8283	Intermediate Similarity	NPC407
0.8283	Intermediate Similarity	NPC307235
0.8276	Intermediate Similarity	NPC102639
0.8273	Intermediate Similarity	NPC94045
0.8269	Intermediate Similarity	NPC79241
0.8269	Intermediate Similarity	NPC6597
0.8261	Intermediate Similarity	NPC121866
0.8246	Intermediate Similarity	NPC219070
0.8246	Intermediate Similarity	NPC470759
0.8246	Intermediate Similarity	NPC127894
0.8246	Intermediate Similarity	NPC164386
0.8246	Intermediate Similarity	NPC293619
0.8246	Intermediate Similarity	NPC15860
0.8246	Intermediate Similarity	NPC474933
0.8241	Intermediate Similarity	NPC469913
0.8235	Intermediate Similarity	NPC306884
0.8235	Intermediate Similarity	NPC94139
0.8235	Intermediate Similarity	NPC147284
0.8235	Intermediate Similarity	NPC162314
0.8235	Intermediate Similarity	NPC210497
0.8235	Intermediate Similarity	NPC3358
0.8235	Intermediate Similarity	NPC477213
0.823	Intermediate Similarity	NPC167934
0.823	Intermediate Similarity	NPC464
0.823	Intermediate Similarity	NPC185541
0.8224	Intermediate Similarity	NPC272029
0.8224	Intermediate Similarity	NPC292792
0.822	Intermediate Similarity	NPC248786
0.822	Intermediate Similarity	NPC261992
0.8218	Intermediate Similarity	NPC192
0.8218	Intermediate Similarity	NPC312304
0.8218	Intermediate Similarity	NPC71853
0.8214	Intermediate Similarity	NPC190212
0.8208	Intermediate Similarity	NPC51633
0.8205	Intermediate Similarity	NPC476633
0.8198	Intermediate Similarity	NPC296920
0.8198	Intermediate Similarity	NPC139617
0.8198	Intermediate Similarity	NPC78918
0.8198	Intermediate Similarity	NPC90520
0.819	Intermediate Similarity	NPC299762
0.819	Intermediate Similarity	NPC33675
0.8182	Intermediate Similarity	NPC155393
0.8182	Intermediate Similarity	NPC266691
0.8174	Intermediate Similarity	NPC139047
0.8174	Intermediate Similarity	NPC470626
0.8174	Intermediate Similarity	NPC212743
0.8174	Intermediate Similarity	NPC474612
0.8173	Intermediate Similarity	NPC259512
0.8173	Intermediate Similarity	NPC312132
0.8167	Intermediate Similarity	NPC245060
0.8165	Intermediate Similarity	NPC66834
0.8165	Intermediate Similarity	NPC194034
0.8165	Intermediate Similarity	NPC227894
0.8165	Intermediate Similarity	NPC251306
0.8158	Intermediate Similarity	NPC114064
0.8158	Intermediate Similarity	NPC221049
0.8158	Intermediate Similarity	NPC85292
0.8158	Intermediate Similarity	NPC54507
0.8158	Intermediate Similarity	NPC229147
0.8155	Intermediate Similarity	NPC152415
0.8151	Intermediate Similarity	NPC474237
0.8151	Intermediate Similarity	NPC4012

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 NPC233320 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	275
0.1-0.2	1100
0.2-0.3	1591
0.3-0.4	2648
0.4-0.5	1759
0.5-0.6	1070
0.6-0.7	579
0.7-0.8	117
0.8-0.85	8
0.85-0.9	2
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9074	High Similarity	NPD6671	Approved
0.8641	High Similarity	NPD289	Clinical (unspecified phase)
0.8585	High Similarity	NPD968	Approved
0.8532	High Similarity	NPD228	Approved
0.8435	Intermediate Similarity	NPD3496	Discontinued
0.8431	Intermediate Similarity	NPD844	Approved
0.8384	Intermediate Similarity	NPD9295	Approved
0.8173	Intermediate Similarity	NPD288	Approved
0.8165	Intermediate Similarity	NPD290	Approved
0.8099	Intermediate Similarity	NPD2861	Phase 2
0.8067	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.8053	Intermediate Similarity	NPD1398	Phase 1
0.8034	Intermediate Similarity	NPD4626	Approved
0.8033	Intermediate Similarity	NPD600	Approved
0.8033	Intermediate Similarity	NPD596	Approved
0.8	Intermediate Similarity	NPD6696	Suspended
0.7983	Intermediate Similarity	NPD2230	Approved
0.7983	Intermediate Similarity	NPD2232	Approved
0.7983	Intermediate Similarity	NPD2233	Approved
0.7928	Intermediate Similarity	NPD2684	Approved
0.7913	Intermediate Similarity	NPD709	Approved
0.7885	Intermediate Similarity	NPD845	Approved
0.7881	Intermediate Similarity	NPD1778	Approved
0.7845	Intermediate Similarity	NPD7340	Approved
0.784	Intermediate Similarity	NPD839	Approved
0.784	Intermediate Similarity	NPD840	Approved
0.781	Intermediate Similarity	NPD2934	Approved
0.781	Intermediate Similarity	NPD2933	Approved
0.781	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.7807	Intermediate Similarity	NPD821	Approved
0.7807	Intermediate Similarity	NPD7635	Approved
0.7769	Intermediate Similarity	NPD4749	Approved
0.7739	Intermediate Similarity	NPD5283	Phase 1
0.7736	Intermediate Similarity	NPD2860	Approved
0.7736	Intermediate Similarity	NPD2859	Approved
0.7712	Intermediate Similarity	NPD1548	Phase 1
0.7706	Intermediate Similarity	NPD940	Approved
0.7706	Intermediate Similarity	NPD846	Approved
0.7686	Intermediate Similarity	NPD2235	Phase 2
0.7686	Intermediate Similarity	NPD2231	Phase 2
0.7685	Intermediate Similarity	NPD3020	Approved
0.7652	Intermediate Similarity	NPD1138	Approved
0.7652	Intermediate Similarity	NPD7843	Approved
0.7647	Intermediate Similarity	NPD5691	Approved
0.7647	Intermediate Similarity	NPD1357	Approved
0.7624	Intermediate Similarity	NPD111	Approved
0.7615	Intermediate Similarity	NPD2935	Discontinued
0.7607	Intermediate Similarity	NPD7157	Approved
0.7603	Intermediate Similarity	NPD1611	Approved
0.7603	Intermediate Similarity	NPD1610	Phase 2
0.7581	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7581	Intermediate Similarity	NPD6584	Phase 3
0.757	Intermediate Similarity	NPD1809	Phase 2
0.7565	Intermediate Similarity	NPD1137	Approved
0.7565	Intermediate Similarity	NPD1139	Approved
0.7544	Intermediate Similarity	NPD5451	Approved
0.7544	Intermediate Similarity	NPD4750	Phase 3
0.754	Intermediate Similarity	NPD3027	Phase 3
0.754	Intermediate Similarity	NPD4625	Phase 3
0.752	Intermediate Similarity	NPD1712	Approved
0.75	Intermediate Similarity	NPD4060	Phase 1
0.748	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.748	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7477	Intermediate Similarity	NPD9296	Approved
0.746	Intermediate Similarity	NPD4908	Phase 1
0.746	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7459	Intermediate Similarity	NPD1535	Discovery
0.7459	Intermediate Similarity	NPD422	Phase 1
0.7459	Intermediate Similarity	NPD1091	Approved
0.7438	Intermediate Similarity	NPD2667	Approved
0.7438	Intermediate Similarity	NPD2668	Approved
0.7434	Intermediate Similarity	NPD1445	Approved
0.7434	Intermediate Similarity	NPD1444	Approved
0.7434	Intermediate Similarity	NPD3134	Approved
0.7398	Intermediate Similarity	NPD1481	Phase 2
0.7391	Intermediate Similarity	NPD3021	Approved
0.7391	Intermediate Similarity	NPD3022	Approved
0.7381	Intermediate Similarity	NPD2237	Approved
0.7381	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7373	Intermediate Similarity	NPD593	Approved
0.7373	Intermediate Similarity	NPD595	Approved
0.7368	Intermediate Similarity	NPD1358	Approved
0.7364	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7364	Intermediate Similarity	NPD2238	Phase 2
0.7364	Intermediate Similarity	NPD1613	Approved
0.7355	Intermediate Similarity	NPD1651	Approved
0.7355	Intermediate Similarity	NPD5585	Approved
0.7345	Intermediate Similarity	NPD9697	Approved
0.7344	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7339	Intermediate Similarity	NPD1669	Approved
0.7339	Intermediate Similarity	NPD6582	Phase 2
0.7339	Intermediate Similarity	NPD6583	Phase 3
0.7339	Intermediate Similarity	NPD3676	Clinical (unspecified phase)
0.7311	Intermediate Similarity	NPD2557	Approved
0.7302	Intermediate Similarity	NPD4624	Approved
0.7302	Intermediate Similarity	NPD3691	Phase 2
0.7302	Intermediate Similarity	NPD558	Phase 2
0.7302	Intermediate Similarity	NPD3690	Phase 2
0.7297	Intermediate Similarity	NPD1242	Phase 1
0.7287	Intermediate Similarity	NPD2674	Phase 3
0.728	Intermediate Similarity	NPD1283	Approved
0.7273	Intermediate Similarity	NPD9088	Approved
0.7273	Intermediate Similarity	NPD1182	Approved
0.7266	Intermediate Similarity	NPD1024	Discontinued
0.7258	Intermediate Similarity	NPD1608	Approved
0.7252	Intermediate Similarity	NPD4097	Suspended
0.725	Intermediate Similarity	NPD9493	Approved
0.7241	Intermediate Similarity	NPD1792	Phase 2
0.7236	Intermediate Similarity	NPD3847	Discontinued
0.7227	Intermediate Similarity	NPD9618	Approved
0.7227	Intermediate Similarity	NPD9614	Approved
0.7222	Intermediate Similarity	NPD2797	Approved
0.7217	Intermediate Similarity	NPD2342	Discontinued
0.7213	Intermediate Similarity	NPD3445	Approved
0.7213	Intermediate Similarity	NPD3443	Approved
0.7213	Intermediate Similarity	NPD3444	Approved
0.7203	Intermediate Similarity	NPD5535	Approved
0.7196	Intermediate Similarity	NPD9365	Approved
0.719	Intermediate Similarity	NPD5536	Phase 2
0.7177	Intermediate Similarity	NPD3705	Approved
0.7167	Intermediate Similarity	NPD6387	Discontinued
0.7143	Intermediate Similarity	NPD1241	Discontinued
0.7143	Intermediate Similarity	NPD2922	Phase 1
0.7143	Intermediate Similarity	NPD594	Approved
0.7143	Intermediate Similarity	NPD592	Approved
0.7121	Intermediate Similarity	NPD6653	Approved
0.7121	Intermediate Similarity	NPD2157	Approved
0.712	Intermediate Similarity	NPD9717	Approved
0.712	Intermediate Similarity	NPD1840	Phase 2
0.7117	Intermediate Similarity	NPD9273	Approved
0.7109	Intermediate Similarity	NPD3018	Phase 2
0.7109	Intermediate Similarity	NPD9494	Approved
0.7099	Intermediate Similarity	NPD3620	Phase 2
0.7099	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.709	Intermediate Similarity	NPD6032	Approved
0.7087	Intermediate Similarity	NPD1794	Approved
0.7083	Intermediate Similarity	NPD497	Approved
0.7077	Intermediate Similarity	NPD3144	Approved
0.7077	Intermediate Similarity	NPD3145	Approved
0.7073	Intermediate Similarity	NPD6382	Discontinued
0.7073	Intermediate Similarity	NPD3049	Approved
0.7063	Intermediate Similarity	NPD5327	Phase 3
0.7063	Intermediate Similarity	NPD4359	Approved
0.7063	Intermediate Similarity	NPD3685	Discontinued
0.7059	Intermediate Similarity	NPD5177	Phase 3
0.7049	Intermediate Similarity	NPD9613	Approved
0.7049	Intermediate Similarity	NPD9615	Approved
0.7049	Intermediate Similarity	NPD7644	Approved
0.7049	Intermediate Similarity	NPD9616	Approved
0.7045	Intermediate Similarity	NPD447	Suspended
0.704	Intermediate Similarity	NPD1281	Approved
0.7031	Intermediate Similarity	NPD2798	Approved
0.7023	Intermediate Similarity	NPD7477	Discontinued
0.7023	Intermediate Similarity	NPD6233	Phase 2
0.7018	Intermediate Similarity	NPD9500	Approved
0.7016	Intermediate Similarity	NPD5846	Approved
0.7016	Intermediate Similarity	NPD6516	Phase 2
0.7016	Intermediate Similarity	NPD2554	Approved
0.7016	Intermediate Similarity	NPD17	Approved
0.7016	Intermediate Similarity	NPD2556	Approved
0.7016	Intermediate Similarity	NPD2107	Clinical (unspecified phase)
0.7016	Intermediate Similarity	NPD2423	Clinical (unspecified phase)
0.7008	Intermediate Similarity	NPD8651	Approved
0.7	Intermediate Similarity	NPD7095	Approved
0.7	Intermediate Similarity	NPD6090	Discontinued
0.7	Intermediate Similarity	NPD496	Approved
0.7	Intermediate Similarity	NPD498	Approved
0.7	Intermediate Similarity	NPD495	Approved
0.6992	Remote Similarity	NPD2226	Clinical (unspecified phase)
0.6992	Remote Similarity	NPD316	Approved
0.6992	Remote Similarity	NPD3091	Approved
0.6992	Remote Similarity	NPD2486	Discontinued
0.6992	Remote Similarity	NPD1894	Discontinued
0.6975	Remote Similarity	NPD6124	Clinical (unspecified phase)
0.697	Remote Similarity	NPD1240	Approved
0.697	Remote Similarity	NPD4140	Approved
0.697	Remote Similarity	NPD1558	Phase 1
0.6967	Remote Similarity	NPD3596	Phase 2
0.6963	Remote Similarity	NPD6099	Approved
0.6963	Remote Similarity	NPD6100	Approved
0.6957	Remote Similarity	NPD3692	Discontinued
0.6957	Remote Similarity	NPD9610	Approved
0.6957	Remote Similarity	NPD9608	Approved
0.6953	Remote Similarity	NPD1203	Approved
0.6953	Remote Similarity	NPD1770	Clinical (unspecified phase)
0.6953	Remote Similarity	NPD4098	Discontinued
0.6947	Remote Similarity	NPD1048	Approved
0.6947	Remote Similarity	NPD411	Approved
0.6947	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6947	Remote Similarity	NPD3268	Approved
0.6947	Remote Similarity	NPD1039	Discontinued
0.6947	Remote Similarity	NPD6798	Discontinued
0.6942	Remote Similarity	NPD1791	Approved
0.6942	Remote Similarity	NPD1793	Approved
0.6934	Remote Similarity	NPD5698	Clinical (unspecified phase)
0.693	Remote Similarity	NPD291	Approved
0.6929	Remote Similarity	NPD2983	Phase 2
0.6929	Remote Similarity	NPD2982	Phase 2
0.6929	Remote Similarity	NPD1420	Approved
0.6929	Remote Similarity	NPD1421	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