NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	328.24
Volume:	382.273
LogP:	5.579
LogD:	4.534
LogS:	-4.301
# Rotatable Bonds:	8
TPSA:	40.46
# H-Bond Aceptor:	2
# H-Bond Donor:	2
# Rings:	1
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.43
Synthetic Accessibility Score:	2.878
Fsp3:	0.455
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:	-4.791
MDCK Permeability:	2.2110365534899756e-05
Pgp-inhibitor:	0.126
Pgp-substrate:	0.015
Human Intestinal Absorption (HIA):	0.017
20% Bioavailability (F20%):	1.0
30% Bioavailability (F30%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.195
Plasma Protein Binding (PPB):	100.29054260253906%
Volume Distribution (VD):	4.425
Pgp-substrate:	0.48105892539024353%

ADMET: Metabolism

CYP1A2-inhibitor:	0.683
CYP1A2-substrate:	0.752
CYP2C19-inhibitor:	0.618
CYP2C19-substrate:	0.373
CYP2C9-inhibitor:	0.521
CYP2C9-substrate:	0.963
CYP2D6-inhibitor:	0.943
CYP2D6-substrate:	0.933
CYP3A4-inhibitor:	0.415
CYP3A4-substrate:	0.21

ADMET: Excretion

Clearance (CL):	15.753
Half-life (T1/2):	0.899

ADMET: Toxicity

hERG Blockers:	0.054
Human Hepatotoxicity (H-HT):	0.56
Drug-inuced Liver Injury (DILI):	0.019
AMES Toxicity:	0.01
Rat Oral Acute Toxicity:	0.02
Maximum Recommended Daily Dose:	0.694
Skin Sensitization:	0.944
Carcinogencity:	0.074
Eye Corrosion:	0.014
Eye Irritation:	0.936
Respiratory Toxicity:	0.038

Download Data

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

Natural Product: NPC477685

Natural Product ID:	NPC477685
*Common Name:**	2-methyl-5-[(2Z,6Z)-3,7,11-trimethyldodeca-2,6,10-trienyl]benzene-1,4-diol
IUPAC Name:	2-methyl-5-[(2Z,6Z)-3,7,11-trimethyldodeca-2,6,10-trienyl]benzene-1,4-diol
Synonyms:
Standard InCHIKey:	WMICYZWXGIMHIB-NGEVDRGDSA-N
Standard InCHI:	InChI=1S/C22H32O2/c1-16(2)8-6-9-17(3)10-7-11-18(4)12-13-20-15-21(23)19(5)14-22(20)24/h8,10,12,14-15,23-24H,6-7,9,11,13H2,1-5H3/b17-10-,18-12-
SMILES:	CC1=CC(=C(C=C1O)C/C=C(/C)\CC/C=C(/C)\CCC=C(C)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	44566895
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
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10479323]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12350167]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[14640527]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	Axinella verrucosa	Mediterranean	n.a.	PMID[14738391]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15043411]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	Sussex Inlet, New South Wales, Australia	n.a.	PMID[15104517]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15332862]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	Berkeley Pit lake	n.a.	PMID[17970594]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	New Zealand	n.a.	PMID[19323568]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19326880]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20452770]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21126094]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	North Sea	n.a.	PMID[21126094]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	Limonium tubiflorum	n.a.	PMID[21146414]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21916432]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22148349]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22458669]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23360521]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23477451]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23603293]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23972215]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24033077]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24437979]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31433188]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9392888]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[Article]

☑ 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
ED50	5

Activity Type	# Activity
Cell Line	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	ED50	=	4.73	ug/ml	PMID[14640527]
NPT146	Cell Line	SK-OV-3	Homo sapiens	ED50	=	5.31	ug/ml	PMID[14640527]
NPT147	Cell Line	SK-MEL-2	Homo sapiens	ED50	=	4.8	ug/ml	PMID[14640527]
NPT574	Cell Line	XF498	Homo sapiens	ED50	=	5.94	ug/ml	PMID[14640527]
NPT148	Cell Line	HCT-15	Homo sapiens	ED50	=	6.11	ug/ml	PMID[14640527]

☑ 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 NPC477685 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	1694
0.2-0.3	4702
0.3-0.4	14242
0.4-0.5	6321
0.5-0.6	10423
0.6-0.7	3897
0.7-0.8	870
0.8-0.85	181
0.85-0.9	74
0.9-0.95	33
0.95-1	8

Similarity Score	Similarity Level	Natural Product ID
0.9684	High Similarity	NPC248396
0.9684	High Similarity	NPC129373
0.9684	High Similarity	NPC48730
0.9583	High Similarity	NPC80800
0.9579	High Similarity	NPC260775
0.949	High Similarity	NPC47284
0.9479	High Similarity	NPC130756
0.9479	High Similarity	NPC12931
0.9479	High Similarity	NPC70677
0.9474	High Similarity	NPC152097
0.9394	High Similarity	NPC53740
0.9286	High Similarity	NPC108497
0.9271	High Similarity	NPC475078
0.92	High Similarity	NPC155072
0.92	High Similarity	NPC469913
0.9192	High Similarity	NPC272029
0.9184	High Similarity	NPC252105
0.9126	High Similarity	NPC469912
0.9109	High Similarity	NPC474352
0.9091	High Similarity	NPC471228
0.9091	High Similarity	NPC269212
0.9091	High Similarity	NPC235762
0.9082	High Similarity	NPC174911
0.9082	High Similarity	NPC72729
0.9072	High Similarity	NPC79241
0.9072	High Similarity	NPC6597
0.9053	High Similarity	NPC3358
0.9053	High Similarity	NPC162314
0.9053	High Similarity	NPC147284
0.9053	High Similarity	NPC94139
0.9053	High Similarity	NPC210497
0.9053	High Similarity	NPC306884
0.9053	High Similarity	NPC29373
0.901	High Similarity	NPC99836
0.901	High Similarity	NPC12640
0.901	High Similarity	NPC201662
0.9	High Similarity	NPC475225
0.898	High Similarity	NPC299762
0.898	High Similarity	NPC33675
0.8969	High Similarity	NPC312132
0.8969	High Similarity	NPC259512
0.8947	High Similarity	NPC231150
0.8932	High Similarity	NPC26013
0.8932	High Similarity	NPC282855
0.8922	High Similarity	NPC204901
0.8922	High Similarity	NPC158253
0.8922	High Similarity	NPC320439
0.8922	High Similarity	NPC232523
0.8911	High Similarity	NPC37802
0.8857	High Similarity	NPC177962
0.8857	High Similarity	NPC302371
0.8857	High Similarity	NPC62867
0.8846	High Similarity	NPC208229
0.8842	High Similarity	NPC192
0.8835	High Similarity	NPC279887
0.8835	High Similarity	NPC68260
0.8812	High Similarity	NPC218879
0.8812	High Similarity	NPC475580
0.8812	High Similarity	NPC227458
0.8812	High Similarity	NPC244513
0.88	High Similarity	NPC12221
0.8762	High Similarity	NPC266937
0.8762	High Similarity	NPC77772
0.8762	High Similarity	NPC54373
0.8762	High Similarity	NPC470770
0.8738	High Similarity	NPC66834
0.8725	High Similarity	NPC117115
0.87	High Similarity	NPC130103
0.8687	High Similarity	NPC474073
0.8673	High Similarity	NPC32714
0.8667	High Similarity	NPC132720
0.8641	High Similarity	NPC310456
0.8632	High Similarity	NPC27974
0.8614	High Similarity	NPC166313
0.8614	High Similarity	NPC137415
0.8614	High Similarity	NPC294186
0.8614	High Similarity	NPC192032
0.8614	High Similarity	NPC24407
0.8614	High Similarity	NPC147310
0.8614	High Similarity	NPC11280
0.8598	High Similarity	NPC28784
0.8598	High Similarity	NPC296144
0.8571	High Similarity	NPC299568
0.8571	High Similarity	NPC152415
0.8571	High Similarity	NPC245187
0.8571	High Similarity	NPC33728
0.8571	High Similarity	NPC19808
0.8571	High Similarity	NPC98392
0.8571	High Similarity	NPC76938
0.8571	High Similarity	NPC473524
0.8571	High Similarity	NPC186385
0.8558	High Similarity	NPC233320
0.8558	High Similarity	NPC151477
0.8545	High Similarity	NPC206205
0.8532	High Similarity	NPC141001
0.8529	High Similarity	NPC242342
0.8529	High Similarity	NPC302219
0.8529	High Similarity	NPC94351
0.8529	High Similarity	NPC222522
0.8529	High Similarity	NPC85479
0.8529	High Similarity	NPC24404
0.8529	High Similarity	NPC146798
0.8529	High Similarity	NPC249828
0.8529	High Similarity	NPC313030
0.8529	High Similarity	NPC71002
0.8529	High Similarity	NPC168303
0.8529	High Similarity	NPC233827
0.8529	High Similarity	NPC106396
0.8529	High Similarity	NPC53051
0.8526	High Similarity	NPC307235
0.8526	High Similarity	NPC407
0.8519	High Similarity	NPC473931
0.8519	High Similarity	NPC114918
0.8519	High Similarity	NPC474114
0.8519	High Similarity	NPC474050
0.8505	High Similarity	NPC228452
0.8505	High Similarity	NPC166995
0.85	High Similarity	NPC88420
0.8485	Intermediate Similarity	NPC222146
0.8476	Intermediate Similarity	NPC174981
0.8476	Intermediate Similarity	NPC306295
0.8469	Intermediate Similarity	NPC55903
0.8462	Intermediate Similarity	NPC21594
0.8462	Intermediate Similarity	NPC54765
0.8455	Intermediate Similarity	NPC320864
0.8454	Intermediate Similarity	NPC55561
0.8447	Intermediate Similarity	NPC130817
0.844	Intermediate Similarity	NPC232165
0.8438	Intermediate Similarity	NPC19680
0.8431	Intermediate Similarity	NPC72947
0.8431	Intermediate Similarity	NPC284011
0.8426	Intermediate Similarity	NPC263753
0.8426	Intermediate Similarity	NPC23804
0.8421	Intermediate Similarity	NPC155393
0.8411	Intermediate Similarity	NPC275627
0.8411	Intermediate Similarity	NPC228609
0.8411	Intermediate Similarity	NPC224527
0.8367	Intermediate Similarity	NPC306074
0.8365	Intermediate Similarity	NPC138942
0.8364	Intermediate Similarity	NPC69539
0.8351	Intermediate Similarity	NPC242240
0.8351	Intermediate Similarity	NPC318325
0.8351	Intermediate Similarity	NPC123273
0.8351	Intermediate Similarity	NPC280347
0.8351	Intermediate Similarity	NPC177420
0.835	Intermediate Similarity	NPC196479
0.8349	Intermediate Similarity	NPC471534
0.8333	Intermediate Similarity	NPC46940
0.8333	Intermediate Similarity	NPC166761
0.8333	Intermediate Similarity	NPC98372
0.8333	Intermediate Similarity	NPC225506
0.8333	Intermediate Similarity	NPC10588
0.8333	Intermediate Similarity	NPC294741
0.8333	Intermediate Similarity	NPC26615
0.8319	Intermediate Similarity	NPC45663
0.8318	Intermediate Similarity	NPC471535
0.8318	Intermediate Similarity	NPC296683
0.8317	Intermediate Similarity	NPC77492
0.8316	Intermediate Similarity	NPC286904
0.8316	Intermediate Similarity	NPC150837
0.8304	Intermediate Similarity	NPC121866
0.8304	Intermediate Similarity	NPC471449
0.8302	Intermediate Similarity	NPC95344
0.8302	Intermediate Similarity	NPC64586
0.83	Intermediate Similarity	NPC26244
0.83	Intermediate Similarity	NPC274678
0.8288	Intermediate Similarity	NPC187993
0.8288	Intermediate Similarity	NPC238176
0.8286	Intermediate Similarity	NPC67250
0.8286	Intermediate Similarity	NPC30416
0.8269	Intermediate Similarity	NPC238696
0.8269	Intermediate Similarity	NPC288411
0.8269	Intermediate Similarity	NPC323810
0.8269	Intermediate Similarity	NPC93831
0.8265	Intermediate Similarity	NPC312304
0.8257	Intermediate Similarity	NPC76400
0.8257	Intermediate Similarity	NPC190212
0.8257	Intermediate Similarity	NPC261343
0.8257	Intermediate Similarity	NPC319803
0.8257	Intermediate Similarity	NPC117846
0.8247	Intermediate Similarity	NPC113460
0.8247	Intermediate Similarity	NPC25493
0.8246	Intermediate Similarity	NPC48623
0.8246	Intermediate Similarity	NPC168707
0.8241	Intermediate Similarity	NPC176279
0.8241	Intermediate Similarity	NPC151537
0.8241	Intermediate Similarity	NPC95716
0.8241	Intermediate Similarity	NPC260323
0.8235	Intermediate Similarity	NPC128723
0.8235	Intermediate Similarity	NPC122005
0.8235	Intermediate Similarity	NPC252821
0.823	Intermediate Similarity	NPC318581
0.823	Intermediate Similarity	NPC325544
0.823	Intermediate Similarity	NPC477037
0.8224	Intermediate Similarity	NPC58865
0.8218	Intermediate Similarity	NPC473388
0.8214	Intermediate Similarity	NPC48781
0.8214	Intermediate Similarity	NPC9592
0.8208	Intermediate Similarity	NPC61033
0.8208	Intermediate Similarity	NPC305603

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 NPC477685 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	251
0.1-0.2	1073
0.2-0.3	1539
0.3-0.4	2987
0.4-0.5	1810
0.5-0.6	1082
0.6-0.7	343
0.7-0.8	49
0.8-0.85	11
0.85-0.9	2
0.9-0.95	3
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9263	High Similarity	NPD844	Approved
0.9082	High Similarity	NPD289	Clinical (unspecified phase)
0.8969	High Similarity	NPD288	Approved
0.8857	High Similarity	NPD7635	Approved
0.8571	High Similarity	NPD4750	Phase 3
0.844	Intermediate Similarity	NPD6671	Approved
0.83	Intermediate Similarity	NPD2859	Approved
0.83	Intermediate Similarity	NPD2860	Approved
0.8283	Intermediate Similarity	NPD845	Approved
0.8235	Intermediate Similarity	NPD3020	Approved
0.82	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.82	Intermediate Similarity	NPD2934	Approved
0.82	Intermediate Similarity	NPD2933	Approved
0.8119	Intermediate Similarity	NPD1809	Phase 2
0.8077	Intermediate Similarity	NPD846	Approved
0.8077	Intermediate Similarity	NPD940	Approved
0.8037	Intermediate Similarity	NPD2342	Discontinued
0.789	Intermediate Similarity	NPD3021	Approved
0.789	Intermediate Similarity	NPD3022	Approved
0.7881	Intermediate Similarity	NPD6696	Suspended
0.7835	Intermediate Similarity	NPD111	Approved
0.7778	Intermediate Similarity	NPD1444	Approved
0.7778	Intermediate Similarity	NPD1445	Approved
0.7719	Intermediate Similarity	NPD7340	Approved
0.7699	Intermediate Similarity	NPD497	Approved
0.7611	Intermediate Similarity	NPD496	Approved
0.7611	Intermediate Similarity	NPD1398	Phase 1
0.7611	Intermediate Similarity	NPD495	Approved
0.7611	Intermediate Similarity	NPD498	Approved
0.7589	Intermediate Similarity	NPD6124	Clinical (unspecified phase)
0.7568	Intermediate Similarity	NPD1792	Phase 2
0.75	Intermediate Similarity	NPD4749	Approved
0.75	Intermediate Similarity	NPD9500	Approved
0.7477	Intermediate Similarity	NPD1242	Phase 1
0.7474	Intermediate Similarity	NPD9088	Approved
0.7458	Intermediate Similarity	NPD4626	Approved
0.7456	Intermediate Similarity	NPD7159	Clinical (unspecified phase)
0.7436	Intermediate Similarity	NPD3091	Approved
0.7414	Intermediate Similarity	NPD7325	Clinical (unspecified phase)
0.7395	Intermediate Similarity	NPD3496	Discontinued
0.7317	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7311	Intermediate Similarity	NPD2932	Approved
0.7311	Intermediate Similarity	NPD3019	Approved
0.7311	Intermediate Similarity	NPD4059	Approved
0.7304	Intermediate Similarity	NPD2229	Approved
0.7304	Intermediate Similarity	NPD2234	Approved
0.7304	Intermediate Similarity	NPD2228	Approved
0.7297	Intermediate Similarity	NPD968	Approved
0.729	Intermediate Similarity	NPD9273	Approved
0.7288	Intermediate Similarity	NPD2226	Clinical (unspecified phase)
0.7281	Intermediate Similarity	NPD228	Approved
0.7258	Intermediate Similarity	NPD2861	Phase 2
0.7241	Intermediate Similarity	NPD9618	Approved
0.7241	Intermediate Similarity	NPD1791	Approved
0.7241	Intermediate Similarity	NPD1793	Approved
0.7241	Intermediate Similarity	NPD9614	Approved
0.7222	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7213	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD5350	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD5351	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD3092	Approved
0.7167	Intermediate Similarity	NPD2286	Discontinued
0.7156	Intermediate Similarity	NPD3028	Approved
0.7143	Intermediate Similarity	NPD4625	Phase 3
0.7143	Intermediate Similarity	NPD7330	Discontinued
0.7131	Intermediate Similarity	NPD2230	Approved
0.7131	Intermediate Similarity	NPD2232	Approved
0.7131	Intermediate Similarity	NPD2233	Approved
0.7117	Intermediate Similarity	NPD9610	Approved
0.7117	Intermediate Similarity	NPD9608	Approved
0.7107	Intermediate Similarity	NPD1983	Approved
0.7107	Intermediate Similarity	NPD1980	Approved
0.7107	Intermediate Similarity	NPD1981	Approved
0.7097	Intermediate Similarity	NPD3094	Phase 2
0.7083	Intermediate Similarity	NPD4093	Discontinued
0.7083	Intermediate Similarity	NPD5691	Approved
0.7069	Intermediate Similarity	NPD9379	Approved
0.7069	Intermediate Similarity	NPD9377	Approved
0.7059	Intermediate Similarity	NPD9613	Approved
0.7059	Intermediate Similarity	NPD9616	Approved
0.7059	Intermediate Similarity	NPD9615	Approved
0.7053	Intermediate Similarity	NPD9087	Approved
0.7049	Intermediate Similarity	NPD1201	Approved
0.7049	Intermediate Similarity	NPD1611	Approved
0.7025	Intermediate Similarity	NPD3095	Discontinued
0.7025	Intermediate Similarity	NPD1751	Approved
0.7025	Intermediate Similarity	NPD4589	Approved
0.7025	Intermediate Similarity	NPD1778	Approved
0.7019	Intermediate Similarity	NPD9295	Approved
0.7018	Intermediate Similarity	NPD2684	Approved
0.7	Intermediate Similarity	NPD316	Approved
0.7	Intermediate Similarity	NPD5304	Approved
0.7	Intermediate Similarity	NPD5303	Approved
0.6984	Remote Similarity	NPD5736	Approved
0.6984	Remote Similarity	NPD2237	Approved
0.6975	Remote Similarity	NPD405	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD7636	Approved
0.6949	Remote Similarity	NPD1476	Clinical (unspecified phase)
0.6942	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.6942	Remote Similarity	NPD4235	Clinical (unspecified phase)
0.693	Remote Similarity	NPD290	Approved
0.6929	Remote Similarity	NPD600	Approved
0.6929	Remote Similarity	NPD596	Approved
0.6923	Remote Similarity	NPD7843	Approved
0.6917	Remote Similarity	NPD7644	Approved
0.6897	Remote Similarity	NPD9280	Clinical (unspecified phase)
0.6891	Remote Similarity	NPD7157	Approved
0.6891	Remote Similarity	NPD709	Approved
0.6875	Remote Similarity	NPD5700	Clinical (unspecified phase)
0.6864	Remote Similarity	NPD5283	Phase 1
0.6842	Remote Similarity	NPD6099	Approved
0.6842	Remote Similarity	NPD6100	Approved
0.6842	Remote Similarity	NPD2935	Discontinued
0.6837	Remote Similarity	NPD9294	Approved
0.6829	Remote Similarity	NPD3143	Discontinued
0.6825	Remote Similarity	NPD1470	Approved
0.6825	Remote Similarity	NPD4339	Clinical (unspecified phase)
0.681	Remote Similarity	NPD9380	Clinical (unspecified phase)
0.68	Remote Similarity	NPD1755	Approved
0.6772	Remote Similarity	NPD2194	Approved
0.6772	Remote Similarity	NPD6584	Phase 3
0.6772	Remote Similarity	NPD2195	Approved
0.6769	Remote Similarity	NPD839	Approved
0.6769	Remote Similarity	NPD6663	Approved
0.6769	Remote Similarity	NPD840	Approved
0.6763	Remote Similarity	NPD6090	Discontinued
0.675	Remote Similarity	NPD255	Approved
0.675	Remote Similarity	NPD256	Approved
0.6748	Remote Similarity	NPD5238	Clinical (unspecified phase)
0.6748	Remote Similarity	NPD9381	Approved
0.6748	Remote Similarity	NPD9384	Approved
0.6746	Remote Similarity	NPD5310	Approved
0.6746	Remote Similarity	NPD5311	Approved
0.6744	Remote Similarity	NPD3027	Phase 3
0.6742	Remote Similarity	NPD4097	Suspended
0.6733	Remote Similarity	NPD9093	Approved
0.6724	Remote Similarity	NPD74	Approved
0.6724	Remote Similarity	NPD9266	Approved
0.6721	Remote Similarity	NPD1759	Phase 1
0.672	Remote Similarity	NPD2235	Phase 2
0.672	Remote Similarity	NPD3070	Discontinued
0.672	Remote Similarity	NPD2231	Phase 2
0.6719	Remote Similarity	NPD3635	Approved
0.6719	Remote Similarity	NPD3636	Approved
0.6719	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6719	Remote Similarity	NPD3637	Approved
0.6718	Remote Similarity	NPD4060	Phase 1
0.6696	Remote Similarity	NPD1616	Discontinued
0.6694	Remote Similarity	NPD3026	Approved
0.6694	Remote Similarity	NPD9493	Approved
0.6694	Remote Similarity	NPD3023	Approved
0.6694	Remote Similarity	NPD2688	Clinical (unspecified phase)
0.6693	Remote Similarity	NPD3053	Approved
0.6693	Remote Similarity	NPD3055	Approved
0.6667	Remote Similarity	NPD3025	Approved
0.6667	Remote Similarity	NPD475	Phase 2
0.6667	Remote Similarity	NPD9244	Approved
0.6667	Remote Similarity	NPD2605	Approved
0.6667	Remote Similarity	NPD1651	Approved
0.6667	Remote Similarity	NPD9089	Approved
0.6667	Remote Similarity	NPD3024	Approved
0.6667	Remote Similarity	NPD5451	Approved
0.6667	Remote Similarity	NPD9622	Approved
0.6667	Remote Similarity	NPD2606	Approved
0.6667	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4908	Phase 1
0.6642	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6641	Remote Similarity	NPD859	Approved
0.6641	Remote Similarity	NPD602	Approved
0.6641	Remote Similarity	NPD599	Approved
0.6641	Remote Similarity	NPD4624	Approved
0.6641	Remote Similarity	NPD858	Approved
0.664	Remote Similarity	NPD1610	Phase 2
0.6639	Remote Similarity	NPD16	Approved
0.6639	Remote Similarity	NPD1758	Phase 1
0.6639	Remote Similarity	NPD1138	Approved
0.6639	Remote Similarity	NPD821	Approved
0.6639	Remote Similarity	NPD856	Approved
0.6638	Remote Similarity	NPD9263	Approved
0.6638	Remote Similarity	NPD9267	Approved
0.6638	Remote Similarity	NPD9264	Approved
0.6637	Remote Similarity	NPD4818	Approved
0.6637	Remote Similarity	NPD4817	Approved
0.6618	Remote Similarity	NPD4257	Approved
0.6618	Remote Similarity	NPD4256	Phase 2
0.6615	Remote Similarity	NPD5156	Approved
0.6615	Remote Similarity	NPD5155	Approved
0.6614	Remote Similarity	NPD1283	Approved
0.6613	Remote Similarity	NPD2667	Approved
0.6613	Remote Similarity	NPD2668	Approved
0.6612	Remote Similarity	NPD6387	Discontinued
0.6604	Remote Similarity	NPD1101	Approved
0.6591	Remote Similarity	NPD3620	Phase 2
0.6591	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6591	Remote Similarity	NPD2238	Phase 2
0.6591	Remote Similarity	NPD6346	Approved
0.6589	Remote Similarity	NPD1712	Approved
0.6585	Remote Similarity	NPD1548	Phase 1
0.6583	Remote Similarity	NPD4869	Clinical (unspecified phase)
0.6567	Remote Similarity	NPD7718	Clinical (unspecified phase)

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