NPASS Compound

Structure

NPC248396 OpenBabel07101718192D 25 25 0 0 0 0 0 0 0 0999 V2000 2.5981 13.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 12.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 12.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 11.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 10.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 9.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 9.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 8.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 7.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 6.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 0 0 0 2 3 2 0 0 0 0 3 4 1 0 0 0 0 4 5 2 0 0 0 0 5 6 1 0 0 0 0 6 7 1 0 0 0 0 7 8 2 0 0 0 0 8 9 1 0 0 0 0 9 10 1 0 0 0 0 10 11 1 0 0 0 0 11 12 1 0 0 0 0 12 13 1 0 0 0 0 13 14 1 0 0 0 0 14 15 1 0 0 0 0 15 16 1 0 0 0 0 16 17 1 0 0 0 0 17 21 1 0 0 0 0 18 19 1 0 0 0 0 18 22 2 0 0 0 0 19 23 2 0 0 0 0 20 21 2 0 0 0 0 20 22 1 0 0 0 0 21 23 1 0 0 0 0 22 24 1 0 0 0 0 23 25 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	342.26
Volume:	399.569
LogP:	5.202
LogD:	4.156
LogS:	-3.085
# Rotatable Bonds:	13
TPSA:	40.46
# H-Bond Aceptor:	2
# H-Bond Donor:	2
# Rings:	1
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.178
Synthetic Accessibility Score:	2.697
Fsp3:	0.478
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	2
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.928
MDCK Permeability:	2.589356154203415e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.02
20% Bioavailability (F20%):	0.999
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.074
Plasma Protein Binding (PPB):	99.35749816894531%
Volume Distribution (VD):	1.936
Pgp-substrate:	0.3640682101249695%

ADMET: Metabolism

CYP1A2-inhibitor:	0.787
CYP1A2-substrate:	0.438
CYP2C19-inhibitor:	0.875
CYP2C19-substrate:	0.112
CYP2C9-inhibitor:	0.497
CYP2C9-substrate:	0.997
CYP2D6-inhibitor:	0.978
CYP2D6-substrate:	0.958
CYP3A4-inhibitor:	0.735
CYP3A4-substrate:	0.142

ADMET: Excretion

Clearance (CL):	4.317
Half-life (T1/2):	0.898

ADMET: Toxicity

hERG Blockers:	0.238
Human Hepatotoxicity (H-HT):	0.077
Drug-inuced Liver Injury (DILI):	0.05
AMES Toxicity:	0.356
Rat Oral Acute Toxicity:	0.049
Maximum Recommended Daily Dose:	0.613
Skin Sensitization:	0.967
Carcinogencity:	0.128
Eye Corrosion:	0.86
Eye Irritation:	0.982
Respiratory Toxicity:	0.922

Download Data

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

Natural Product: NPC248396

Natural Product ID:	NPC248396
*Common Name:**	10'(Z),13'(E),15'(E)-Heptadecatrienylhydroquinone
IUPAC Name:	2-[(10Z,13E,15E)-heptadeca-10,13,15-trienyl]benzene-1,4-diol
Synonyms:	10'(Z),13'(E),15'(E)-Heptadecatrienylhydroquinone
Standard InCHIKey:	OILIDQCJCUQAGV-YCLNNTPMSA-N
Standard InCHI:	InChI=1S/C23H34O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-21-20-22(24)18-19-23(21)25/h2-5,7-8,18-20,24-25H,6,9-17H2,1H3/b3-2+,5-4+,8-7-
SMILES:	C/C=C/C=C/C/C=CCCCCCCCCCc1cc(ccc1O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL464638
PubChem CID:	11724959
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000134] Phenols [CHEMONTID:0001286] Benzenediols [CHEMONTID:0000136] 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	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO33250	rhus succedanea	Species	Anacardiaceae	Eukaryota	sap	n.a.	n.a.	PMID[12444713]
NPO33250	rhus succedanea	Species	Anacardiaceae	Eukaryota	seed kernels	Fukuoka, Japan	n.a.	PMID[9322359]

☑ 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	5

Activity Type	# Activity
Cell Line	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT165	Cell Line	HeLa	Homo sapiens	IC50	=	2.8	ug.mL-1	PMID[469919]
NPT1229	Cell Line	Huh-7	Homo sapiens	IC50	=	3.9	ug.mL-1	PMID[469919]
NPT393	Cell Line	HCT-116	Homo sapiens	IC50	=	2.0	ug.mL-1	PMID[469919]
NPT114	Cell Line	LoVo	Homo sapiens	IC50	=	4.5	ug.mL-1	PMID[469919]
NPT76	Cell Line	C6	Rattus norvegicus	IC50	=	0.9	ug.mL-1	PMID[469919]

☑ 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 NPC248396 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	239
0.1-0.2	1642
0.2-0.3	4678
0.3-0.4	13920
0.4-0.5	6071
0.5-0.6	10472
0.6-0.7	4318
0.7-0.8	1020
0.8-0.85	172
0.85-0.9	119
0.9-0.95	32
0.95-1	14

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC129373
1.0	High Similarity	NPC48730
0.9892	High Similarity	NPC260775
0.9787	High Similarity	NPC130756
0.9787	High Similarity	NPC12931
0.9787	High Similarity	NPC70677
0.9785	High Similarity	NPC152097
0.9684	High Similarity	NPC477685
0.9583	High Similarity	NPC108497
0.9574	High Similarity	NPC475078
0.949	High Similarity	NPC155072
0.9479	High Similarity	NPC80800
0.9388	High Similarity	NPC47284
0.9355	High Similarity	NPC3358
0.9355	High Similarity	NPC94139
0.9355	High Similarity	NPC306884
0.9355	High Similarity	NPC29373
0.9355	High Similarity	NPC162314
0.9355	High Similarity	NPC147284
0.9355	High Similarity	NPC210497
0.9293	High Similarity	NPC53740
0.9293	High Similarity	NPC469913
0.92	High Similarity	NPC320439
0.9184	High Similarity	NPC269212
0.914	High Similarity	NPC192
0.9091	High Similarity	NPC475580
0.9082	High Similarity	NPC12221
0.9082	High Similarity	NPC252105
0.902	High Similarity	NPC282855
0.902	High Similarity	NPC26013
0.901	High Similarity	NPC474352
0.899	High Similarity	NPC471228
0.899	High Similarity	NPC235762
0.898	High Similarity	NPC72729
0.898	High Similarity	NPC130103
0.898	High Similarity	NPC174911
0.8969	High Similarity	NPC79241
0.8969	High Similarity	NPC6597
0.8969	High Similarity	NPC474073
0.8958	High Similarity	NPC32714
0.8942	High Similarity	NPC62867
0.8942	High Similarity	NPC177962
0.8932	High Similarity	NPC208229
0.8925	High Similarity	NPC27974
0.8922	High Similarity	NPC279887
0.8922	High Similarity	NPC68260
0.89	High Similarity	NPC272029
0.89	High Similarity	NPC475225
0.8878	High Similarity	NPC33675
0.8878	High Similarity	NPC299762
0.8866	High Similarity	NPC312132
0.8866	High Similarity	NPC259512
0.8854	High Similarity	NPC152415
0.8854	High Similarity	NPC245187
0.8854	High Similarity	NPC76938
0.8846	High Similarity	NPC54373
0.8846	High Similarity	NPC266937
0.8846	High Similarity	NPC470770
0.8846	High Similarity	NPC469912
0.8846	High Similarity	NPC77772
0.8842	High Similarity	NPC231150
0.8835	High Similarity	NPC98392
0.8835	High Similarity	NPC473524
0.8824	High Similarity	NPC158253
0.8824	High Similarity	NPC204901
0.8824	High Similarity	NPC232523
0.8824	High Similarity	NPC233320
0.8817	High Similarity	NPC307235
0.8817	High Similarity	NPC407
0.88	High Similarity	NPC24404
0.88	High Similarity	NPC302219
0.88	High Similarity	NPC53051
0.88	High Similarity	NPC94351
0.88	High Similarity	NPC71002
0.88	High Similarity	NPC168303
0.88	High Similarity	NPC222522
0.88	High Similarity	NPC242342
0.88	High Similarity	NPC313030
0.88	High Similarity	NPC85479
0.88	High Similarity	NPC233827
0.88	High Similarity	NPC106396
0.88	High Similarity	NPC146798
0.88	High Similarity	NPC249828
0.8776	High Similarity	NPC88420
0.8762	High Similarity	NPC302371
0.875	High Similarity	NPC55903
0.8737	High Similarity	NPC55561
0.8725	High Similarity	NPC99836
0.8725	High Similarity	NPC201662
0.8725	High Similarity	NPC12640
0.8725	High Similarity	NPC54765
0.8713	High Similarity	NPC130817
0.871	High Similarity	NPC155393
0.87	High Similarity	NPC72947
0.87	High Similarity	NPC137415
0.87	High Similarity	NPC11280
0.87	High Similarity	NPC147310
0.87	High Similarity	NPC166313
0.87	High Similarity	NPC294186
0.87	High Similarity	NPC24407
0.87	High Similarity	NPC284011
0.87	High Similarity	NPC192032
0.8679	High Similarity	NPC296144
0.8679	High Similarity	NPC28784
0.8667	High Similarity	NPC228609
0.8667	High Similarity	NPC275627
0.8646	High Similarity	NPC306074
0.8641	High Similarity	NPC66834
0.8632	High Similarity	NPC177420
0.8632	High Similarity	NPC123273
0.8632	High Similarity	NPC242240
0.8632	High Similarity	NPC280347
0.8632	High Similarity	NPC318325
0.8627	High Similarity	NPC37802
0.8627	High Similarity	NPC138942
0.8614	High Similarity	NPC196479
0.8611	High Similarity	NPC141001
0.8602	High Similarity	NPC286904
0.8602	High Similarity	NPC150837
0.86	High Similarity	NPC10588
0.86	High Similarity	NPC225506
0.86	High Similarity	NPC294741
0.86	High Similarity	NPC166761
0.8598	High Similarity	NPC114918
0.8598	High Similarity	NPC474114
0.8598	High Similarity	NPC474050
0.8598	High Similarity	NPC473931
0.8586	High Similarity	NPC77492
0.8571	High Similarity	NPC274678
0.8571	High Similarity	NPC471535
0.8571	High Similarity	NPC222146
0.8571	High Similarity	NPC26244
0.8558	High Similarity	NPC95344
0.8544	High Similarity	NPC310456
0.8544	High Similarity	NPC67250
0.8542	High Similarity	NPC312304
0.8529	High Similarity	NPC323810
0.8529	High Similarity	NPC288411
0.8529	High Similarity	NPC227458
0.8529	High Similarity	NPC244513
0.8529	High Similarity	NPC93831
0.8529	High Similarity	NPC218879
0.8526	High Similarity	NPC113460
0.8526	High Similarity	NPC19680
0.8526	High Similarity	NPC25493
0.85	High Similarity	NPC252821
0.85	High Similarity	NPC128723
0.85	High Similarity	NPC122005
0.8485	Intermediate Similarity	NPC473388
0.8476	Intermediate Similarity	NPC33728
0.8476	Intermediate Similarity	NPC19808
0.8469	Intermediate Similarity	NPC128062
0.8469	Intermediate Similarity	NPC27323
0.8469	Intermediate Similarity	NPC316301
0.8469	Intermediate Similarity	NPC289769
0.8469	Intermediate Similarity	NPC151715
0.8462	Intermediate Similarity	NPC61033
0.8462	Intermediate Similarity	NPC305603
0.8455	Intermediate Similarity	NPC206205
0.8454	Intermediate Similarity	NPC204210
0.8454	Intermediate Similarity	NPC304541
0.8447	Intermediate Similarity	NPC134829
0.8447	Intermediate Similarity	NPC117115
0.844	Intermediate Similarity	NPC69539
0.8438	Intermediate Similarity	NPC258219
0.8431	Intermediate Similarity	NPC168829
0.8426	Intermediate Similarity	NPC197513
0.8426	Intermediate Similarity	NPC471534
0.8421	Intermediate Similarity	NPC23167
0.8411	Intermediate Similarity	NPC98372
0.8411	Intermediate Similarity	NPC474920
0.8411	Intermediate Similarity	NPC166995
0.8411	Intermediate Similarity	NPC228452
0.84	Intermediate Similarity	NPC156313
0.8396	Intermediate Similarity	NPC296683
0.8396	Intermediate Similarity	NPC132720
0.8384	Intermediate Similarity	NPC8392
0.8381	Intermediate Similarity	NPC306295
0.8381	Intermediate Similarity	NPC174981
0.8378	Intermediate Similarity	NPC323074
0.8367	Intermediate Similarity	NPC271440
0.8365	Intermediate Similarity	NPC118286
0.8365	Intermediate Similarity	NPC477814
0.8365	Intermediate Similarity	NPC109691
0.8365	Intermediate Similarity	NPC470700
0.8365	Intermediate Similarity	NPC39664
0.8365	Intermediate Similarity	NPC302681
0.8365	Intermediate Similarity	NPC39097
0.8364	Intermediate Similarity	NPC320864
0.8364	Intermediate Similarity	NPC187993
0.8364	Intermediate Similarity	NPC238176
0.835	Intermediate Similarity	NPC102216
0.835	Intermediate Similarity	NPC241891
0.8349	Intermediate Similarity	NPC232165
0.8349	Intermediate Similarity	NPC473718
0.8333	Intermediate Similarity	NPC76400
0.8318	Intermediate Similarity	NPC476632
0.8318	Intermediate Similarity	NPC225679
0.8318	Intermediate Similarity	NPC165770
0.8318	Intermediate Similarity	NPC224527

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 NPC248396 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	242
0.1-0.2	1052
0.2-0.3	1409
0.3-0.4	2927
0.4-0.5	1894
0.5-0.6	1139
0.6-0.7	405
0.7-0.8	65
0.8-0.85	11
0.85-0.9	4
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9375	High Similarity	NPD289	Clinical (unspecified phase)
0.9158	High Similarity	NPD844	Approved
0.8866	High Similarity	NPD288	Approved
0.8762	High Similarity	NPD7635	Approved
0.8692	High Similarity	NPD6671	Approved
0.8571	High Similarity	NPD2860	Approved
0.8571	High Similarity	NPD2859	Approved
0.8557	High Similarity	NPD845	Approved
0.85	High Similarity	NPD3020	Approved
0.8469	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.8469	Intermediate Similarity	NPD2933	Approved
0.8469	Intermediate Similarity	NPD2934	Approved
0.8333	Intermediate Similarity	NPD940	Approved
0.8333	Intermediate Similarity	NPD846	Approved
0.8302	Intermediate Similarity	NPD4750	Phase 3
0.82	Intermediate Similarity	NPD1809	Phase 2
0.8131	Intermediate Similarity	NPD3022	Approved
0.8131	Intermediate Similarity	NPD3021	Approved
0.8105	Intermediate Similarity	NPD111	Approved
0.8019	Intermediate Similarity	NPD1444	Approved
0.8019	Intermediate Similarity	NPD1445	Approved
0.7944	Intermediate Similarity	NPD2342	Discontinued
0.7798	Intermediate Similarity	NPD1792	Phase 2
0.7742	Intermediate Similarity	NPD9088	Approved
0.7714	Intermediate Similarity	NPD1242	Phase 1
0.7658	Intermediate Similarity	NPD6124	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD6696	Suspended
0.7611	Intermediate Similarity	NPD497	Approved
0.7607	Intermediate Similarity	NPD3496	Discontinued
0.757	Intermediate Similarity	NPD9500	Approved
0.7524	Intermediate Similarity	NPD9273	Approved
0.7523	Intermediate Similarity	NPD968	Approved
0.7522	Intermediate Similarity	NPD495	Approved
0.7522	Intermediate Similarity	NPD2228	Approved
0.7522	Intermediate Similarity	NPD2229	Approved
0.7522	Intermediate Similarity	NPD2234	Approved
0.7522	Intermediate Similarity	NPD498	Approved
0.7522	Intermediate Similarity	NPD7159	Clinical (unspecified phase)
0.7522	Intermediate Similarity	NPD496	Approved
0.75	Intermediate Similarity	NPD228	Approved
0.75	Intermediate Similarity	NPD2226	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD3091	Approved
0.7478	Intermediate Similarity	NPD7340	Approved
0.7459	Intermediate Similarity	NPD2861	Phase 2
0.7456	Intermediate Similarity	NPD1791	Approved
0.7456	Intermediate Similarity	NPD9614	Approved
0.7456	Intermediate Similarity	NPD1793	Approved
0.7456	Intermediate Similarity	NPD9618	Approved
0.7417	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7395	Intermediate Similarity	NPD5351	Clinical (unspecified phase)
0.7395	Intermediate Similarity	NPD5350	Clinical (unspecified phase)
0.7383	Intermediate Similarity	NPD3028	Approved
0.7373	Intermediate Similarity	NPD4626	Approved
0.7373	Intermediate Similarity	NPD3019	Approved
0.7373	Intermediate Similarity	NPD2932	Approved
0.7373	Intermediate Similarity	NPD4059	Approved
0.7368	Intermediate Similarity	NPD1398	Phase 1
0.7339	Intermediate Similarity	NPD9610	Approved
0.7339	Intermediate Similarity	NPD9608	Approved
0.7333	Intermediate Similarity	NPD2232	Approved
0.7333	Intermediate Similarity	NPD2233	Approved
0.7333	Intermediate Similarity	NPD2230	Approved
0.7328	Intermediate Similarity	NPD7325	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD9087	Approved
0.7288	Intermediate Similarity	NPD4093	Discontinued
0.7281	Intermediate Similarity	NPD9379	Approved
0.7281	Intermediate Similarity	NPD9377	Approved
0.7273	Intermediate Similarity	NPD4749	Approved
0.7265	Intermediate Similarity	NPD9613	Approved
0.7265	Intermediate Similarity	NPD9616	Approved
0.7265	Intermediate Similarity	NPD9615	Approved
0.7255	Intermediate Similarity	NPD9295	Approved
0.725	Intermediate Similarity	NPD3092	Approved
0.7232	Intermediate Similarity	NPD2684	Approved
0.7227	Intermediate Similarity	NPD4589	Approved
0.7203	Intermediate Similarity	NPD5303	Approved
0.7203	Intermediate Similarity	NPD316	Approved
0.7203	Intermediate Similarity	NPD7330	Discontinued
0.7203	Intermediate Similarity	NPD5304	Approved
0.7179	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7155	Intermediate Similarity	NPD1476	Clinical (unspecified phase)
0.7154	Intermediate Similarity	NPD3094	Phase 2
0.7143	Intermediate Similarity	NPD290	Approved
0.713	Intermediate Similarity	NPD7843	Approved
0.712	Intermediate Similarity	NPD600	Approved
0.712	Intermediate Similarity	NPD596	Approved
0.7107	Intermediate Similarity	NPD1201	Approved
0.7105	Intermediate Similarity	NPD9280	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7094	Intermediate Similarity	NPD7157	Approved
0.7094	Intermediate Similarity	NPD709	Approved
0.7083	Intermediate Similarity	NPD2286	Discontinued
0.7083	Intermediate Similarity	NPD3095	Discontinued
0.7083	Intermediate Similarity	NPD1751	Approved
0.7083	Intermediate Similarity	NPD9294	Approved
0.7069	Intermediate Similarity	NPD5283	Phase 1
0.7063	Intermediate Similarity	NPD4625	Phase 3
0.704	Intermediate Similarity	NPD5736	Approved
0.7034	Intermediate Similarity	NPD7636	Approved
0.7025	Intermediate Similarity	NPD1981	Approved
0.7025	Intermediate Similarity	NPD1980	Approved
0.7025	Intermediate Similarity	NPD1983	Approved
0.7023	Intermediate Similarity	NPD2935	Discontinued
0.7018	Intermediate Similarity	NPD9380	Clinical (unspecified phase)
0.7016	Intermediate Similarity	NPD4339	Clinical (unspecified phase)
0.7008	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD5691	Approved
0.7	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD4235	Clinical (unspecified phase)
0.6992	Remote Similarity	NPD1755	Approved
0.6967	Remote Similarity	NPD1611	Approved
0.696	Remote Similarity	NPD6584	Phase 3
0.6953	Remote Similarity	NPD839	Approved
0.6953	Remote Similarity	NPD840	Approved
0.6949	Remote Similarity	NPD255	Approved
0.6949	Remote Similarity	NPD256	Approved
0.6942	Remote Similarity	NPD5238	Clinical (unspecified phase)
0.6942	Remote Similarity	NPD1778	Approved
0.6942	Remote Similarity	NPD9381	Approved
0.6942	Remote Similarity	NPD9384	Approved
0.6935	Remote Similarity	NPD5310	Approved
0.6935	Remote Similarity	NPD5311	Approved
0.693	Remote Similarity	NPD9266	Approved
0.693	Remote Similarity	NPD74	Approved
0.6929	Remote Similarity	NPD3027	Phase 3
0.6917	Remote Similarity	NPD1759	Phase 1
0.6911	Remote Similarity	NPD2235	Phase 2
0.6911	Remote Similarity	NPD2231	Phase 2
0.69	Remote Similarity	NPD9089	Approved
0.6899	Remote Similarity	NPD4060	Phase 1
0.6891	Remote Similarity	NPD9493	Approved
0.6885	Remote Similarity	NPD3143	Discontinued
0.688	Remote Similarity	NPD1470	Approved
0.688	Remote Similarity	NPD3055	Approved
0.688	Remote Similarity	NPD3053	Approved
0.687	Remote Similarity	NPD5451	Approved
0.6864	Remote Similarity	NPD475	Phase 2
0.6855	Remote Similarity	NPD9622	Approved
0.685	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.685	Remote Similarity	NPD4908	Phase 1
0.6847	Remote Similarity	NPD4818	Approved
0.6847	Remote Similarity	NPD4817	Approved
0.6842	Remote Similarity	NPD9263	Approved
0.6842	Remote Similarity	NPD9267	Approved
0.6842	Remote Similarity	NPD9264	Approved
0.6838	Remote Similarity	NPD1138	Approved
0.6838	Remote Similarity	NPD821	Approved
0.6833	Remote Similarity	NPD1758	Phase 1
0.6833	Remote Similarity	NPD16	Approved
0.6833	Remote Similarity	NPD856	Approved
0.6829	Remote Similarity	NPD1610	Phase 2
0.6825	Remote Similarity	NPD2195	Approved
0.6825	Remote Similarity	NPD2194	Approved
0.6822	Remote Similarity	NPD6663	Approved
0.6807	Remote Similarity	NPD6387	Discontinued
0.6803	Remote Similarity	NPD2668	Approved
0.6803	Remote Similarity	NPD2667	Approved
0.68	Remote Similarity	NPD9093	Approved
0.6786	Remote Similarity	NPD5700	Clinical (unspecified phase)
0.6777	Remote Similarity	NPD1548	Phase 1
0.6774	Remote Similarity	NPD3070	Discontinued
0.6772	Remote Similarity	NPD2237	Approved
0.6772	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6772	Remote Similarity	NPD3636	Approved
0.6772	Remote Similarity	NPD3637	Approved
0.6772	Remote Similarity	NPD3635	Approved
0.6772	Remote Similarity	NPD1712	Approved
0.6769	Remote Similarity	NPD6346	Approved
0.6769	Remote Similarity	NPD2238	Phase 2
0.6752	Remote Similarity	NPD1139	Approved
0.6752	Remote Similarity	NPD1137	Approved
0.6748	Remote Similarity	NPD3023	Approved
0.6748	Remote Similarity	NPD2688	Clinical (unspecified phase)
0.6748	Remote Similarity	NPD3026	Approved
0.6746	Remote Similarity	NPD1135	Approved
0.6746	Remote Similarity	NPD1131	Approved
0.6746	Remote Similarity	NPD2797	Approved
0.6746	Remote Similarity	NPD1129	Approved
0.6746	Remote Similarity	NPD1134	Approved
0.6746	Remote Similarity	NPD1133	Approved
0.6744	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6726	Remote Similarity	NPD9244	Approved
0.6721	Remote Similarity	NPD3024	Approved
0.6721	Remote Similarity	NPD3025	Approved
0.6721	Remote Similarity	NPD1357	Approved
0.672	Remote Similarity	NPD6582	Phase 2
0.672	Remote Similarity	NPD4659	Approved
0.672	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.672	Remote Similarity	NPD6583	Phase 3
0.6719	Remote Similarity	NPD2605	Approved
0.6719	Remote Similarity	NPD2606	Approved
0.6696	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.6695	Remote Similarity	NPD5535	Approved
0.6694	Remote Similarity	NPD7644	Approved
0.6694	Remote Similarity	NPD317	Approved
0.6694	Remote Similarity	NPD422	Phase 1
0.6694	Remote Similarity	NPD1535	Discovery
0.6694	Remote Similarity	NPD318	Approved
0.6693	Remote Similarity	NPD858	Approved
0.6693	Remote Similarity	NPD9620	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