NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	208.15
Volume:	234.519
LogP:	4.579
LogD:	3.919
LogS:	-3.081
# Rotatable Bonds:	5
TPSA:	40.46
# H-Bond Aceptor:	2
# H-Bond Donor:	2
# Rings:	1
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.727
Synthetic Accessibility Score:	2.099
Fsp3:	0.538
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:	-4.71
MDCK Permeability:	2.1808984456583858e-05
Pgp-inhibitor:	0.02
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.999
30% Bioavailability (F30%):	0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.203
Plasma Protein Binding (PPB):	96.43190002441406%
Volume Distribution (VD):	1.917
Pgp-substrate:	3.672577381134033%

ADMET: Metabolism

CYP1A2-inhibitor:	0.953
CYP1A2-substrate:	0.915
CYP2C19-inhibitor:	0.818
CYP2C19-substrate:	0.29
CYP2C9-inhibitor:	0.422
CYP2C9-substrate:	0.933
CYP2D6-inhibitor:	0.845
CYP2D6-substrate:	0.879
CYP3A4-inhibitor:	0.167
CYP3A4-substrate:	0.174

ADMET: Excretion

Clearance (CL):	10.196
Half-life (T1/2):	0.762

ADMET: Toxicity

hERG Blockers:	0.027
Human Hepatotoxicity (H-HT):	0.044
Drug-inuced Liver Injury (DILI):	0.03
AMES Toxicity:	0.219
Rat Oral Acute Toxicity:	0.28
Maximum Recommended Daily Dose:	0.175
Skin Sensitization:	0.94
Carcinogencity:	0.05
Eye Corrosion:	0.888
Eye Irritation:	0.975
Respiratory Toxicity:	0.746

Download Data

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

Natural Product: NPC227458

Natural Product ID:	NPC227458
*Common Name:**	2-Hexyl-5-Methylresorcinol
IUPAC Name:	2-hexyl-5-methylbenzene-1,3-diol
Synonyms:
Standard InCHIKey:	XPKLONXIXRADCG-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C13H20O2/c1-3-4-5-6-7-11-12(14)8-10(2)9-13(11)15/h8-9,14-15H,3-7H2,1-2H3
SMILES:	CCCCCCc1c(cc(C)cc1O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL496836
PubChem CID:	11535811
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000134] Phenols [CHEMONTID:0001286] Benzenediols [CHEMONTID:0000137] Resorcinols

*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
NPO33648	Pseudomonas sp. Ki19	Species	Pseudomonadaceae	Bacteria	n.a.	n.a.	n.a.	PMID[16643045]
NPO25696	Hyptis brevipes	Species	Lamiaceae	Eukaryota	Whole Plant	Tawangmangu village, Karanganyar, Central Java, Indonesia	2003-FEB	PMID[19422206]
NPO25696	Hyptis brevipes	Species	Lamiaceae	Eukaryota	n.a.	whole plant	n.a.	PMID[19422206]
NPO25696	Hyptis brevipes	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23282042]
NPO17878	Ips paraconfusus	Species	Curculionidae	Eukaryota	n.a.	n.a.	n.a.	PMID[24318848]
NPO25696	Hyptis brevipes	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[28099005]
NPO18407	Pteris fauriei	Species	Pteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12468	Asarum heterotropoides	Species	Aristolochiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO12468	Asarum heterotropoides	Species	Aristolochiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO18446	Paradendryphiella salina	Species	Pleosporaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18407	Pteris fauriei	Species	Pteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19816	Crotalaria novae-hollandiae	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12468	Asarum heterotropoides	Species	Aristolochiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14138	Centaurea aspera	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17878	Ips paraconfusus	Species	Curculionidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25696	Hyptis brevipes	Species	Lamiaceae	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
MIC	8

Activity Type	# Activity
Organism	8

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT87	Organism	Aspergillus fumigatus	Aspergillus fumigatus	MIC	=	10.0	ug.mL-1	PMID[528328]
NPT20	Organism	Candida albicans	Candida albicans	MIC	=	50.0	ug.mL-1	PMID[528328]
NPT1278	Organism	Fusarium culmorum	Fusarium culmorum	MIC	=	50.0	ug.mL-1	PMID[528328]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	2.0	ug.mL-1	PMID[528328]
NPT87	Organism	Aspergillus fumigatus	Aspergillus fumigatus	MIC	=	50.0	ug.mL-1	PMID[528328]
NPT2647	Organism	Drechslera	Drechslera	MIC	=	50.0	ug.mL-1	PMID[528328]
NPT1278	Organism	Fusarium culmorum	Fusarium culmorum	MIC	=	10.0	ug.mL-1	PMID[528328]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	1.0	ug.mL-1	PMID[528328]

☑ 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 NPC227458 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	275
0.1-0.2	1833
0.2-0.3	5653
0.3-0.4	14185
0.4-0.5	4884
0.5-0.6	8514
0.6-0.7	5588
0.7-0.8	1439
0.8-0.85	186
0.85-0.9	79
0.9-0.95	48
0.95-1	13

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC244513
1.0	High Similarity	NPC218879
0.9897	High Similarity	NPC37802
0.9796	High Similarity	NPC12640
0.9796	High Similarity	NPC201662
0.9796	High Similarity	NPC99836
0.9697	High Similarity	NPC232523
0.9697	High Similarity	NPC158253
0.9697	High Similarity	NPC204901
0.96	High Similarity	NPC174981
0.9505	High Similarity	NPC299568
0.9505	High Similarity	NPC186385
0.9505	High Similarity	NPC33728
0.9505	High Similarity	NPC19808
0.9388	High Similarity	NPC24407
0.9388	High Similarity	NPC11280
0.9388	High Similarity	NPC166313
0.9388	High Similarity	NPC137415
0.9388	High Similarity	NPC294186
0.9388	High Similarity	NPC192032
0.9388	High Similarity	NPC147310
0.932	High Similarity	NPC224527
0.9293	High Similarity	NPC94351
0.9293	High Similarity	NPC85479
0.9293	High Similarity	NPC146798
0.9293	High Similarity	NPC249828
0.9293	High Similarity	NPC222522
0.9293	High Similarity	NPC313030
0.9293	High Similarity	NPC71002
0.9293	High Similarity	NPC106396
0.9293	High Similarity	NPC168303
0.9293	High Similarity	NPC53051
0.9293	High Similarity	NPC242342
0.9293	High Similarity	NPC302219
0.9293	High Similarity	NPC24404
0.9286	High Similarity	NPC166761
0.9286	High Similarity	NPC10588
0.9231	High Similarity	NPC166995
0.9223	High Similarity	NPC224870
0.92	High Similarity	NPC102216
0.9192	High Similarity	NPC284011
0.9192	High Similarity	NPC72947
0.9143	High Similarity	NPC263753
0.9143	High Similarity	NPC319803
0.9143	High Similarity	NPC117846
0.9143	High Similarity	NPC23804
0.9062	High Similarity	NPC295295
0.901	High Similarity	NPC241891
0.9	High Similarity	NPC100340
0.9	High Similarity	NPC143659
0.899	High Similarity	NPC80027
0.8972	High Similarity	NPC84999
0.8972	High Similarity	NPC246760
0.8962	High Similarity	NPC261343
0.8952	High Similarity	NPC165770
0.8952	High Similarity	NPC476632
0.8952	High Similarity	NPC225679
0.8952	High Similarity	NPC4493
0.8932	High Similarity	NPC61033
0.8932	High Similarity	NPC305603
0.8922	High Similarity	NPC134829
0.8922	High Similarity	NPC246056
0.89	High Similarity	NPC72729
0.8889	High Similarity	NPC79241
0.8889	High Similarity	NPC6597
0.8868	High Similarity	NPC473521
0.8868	High Similarity	NPC43525
0.8835	High Similarity	NPC39664
0.8835	High Similarity	NPC109691
0.8835	High Similarity	NPC470700
0.8835	High Similarity	NPC118286
0.8835	High Similarity	NPC302681
0.8835	High Similarity	NPC39097
0.8824	High Similarity	NPC30506
0.8824	High Similarity	NPC119860
0.8812	High Similarity	NPC477685
0.88	High Similarity	NPC33675
0.88	High Similarity	NPC299762
0.8788	High Similarity	NPC312132
0.8788	High Similarity	NPC259512
0.8763	High Similarity	NPC231150
0.875	High Similarity	NPC66834
0.875	High Similarity	NPC54844
0.8738	High Similarity	NPC474839
0.8738	High Similarity	NPC292452
0.8727	High Similarity	NPC144343
0.8727	High Similarity	NPC9592
0.8727	High Similarity	NPC48781
0.8727	High Similarity	NPC190514
0.8727	High Similarity	NPC206
0.8725	High Similarity	NPC235762
0.8725	High Similarity	NPC471228
0.8716	High Similarity	NPC115808
0.8713	High Similarity	NPC174911
0.8704	High Similarity	NPC107240
0.87	High Similarity	NPC291789
0.8679	High Similarity	NPC168657
0.8667	High Similarity	NPC63698
0.8667	High Similarity	NPC61885
0.8667	High Similarity	NPC306295
0.8654	High Similarity	NPC248904
0.8649	High Similarity	NPC184302
0.8649	High Similarity	NPC191866
0.8641	High Similarity	NPC475225
0.8636	High Similarity	NPC470760
0.8627	High Similarity	NPC252105
0.8624	High Similarity	NPC808
0.8585	High Similarity	NPC202647
0.8558	High Similarity	NPC471350
0.8558	High Similarity	NPC47284
0.8545	High Similarity	NPC150624
0.8532	High Similarity	NPC249270
0.8529	High Similarity	NPC161571
0.8529	High Similarity	NPC248573
0.8529	High Similarity	NPC275053
0.8529	High Similarity	NPC48730
0.8529	High Similarity	NPC248396
0.8529	High Similarity	NPC129373
0.8515	High Similarity	NPC152097
0.8496	Intermediate Similarity	NPC218753
0.8496	Intermediate Similarity	NPC24125
0.8485	Intermediate Similarity	NPC3358
0.8485	Intermediate Similarity	NPC147284
0.8485	Intermediate Similarity	NPC210497
0.8485	Intermediate Similarity	NPC162314
0.8485	Intermediate Similarity	NPC94139
0.8485	Intermediate Similarity	NPC306884
0.8476	Intermediate Similarity	NPC469913
0.8476	Intermediate Similarity	NPC53740
0.8476	Intermediate Similarity	NPC310456
0.8469	Intermediate Similarity	NPC192
0.8468	Intermediate Similarity	NPC277588
0.8468	Intermediate Similarity	NPC69261
0.8468	Intermediate Similarity	NPC33270
0.8462	Intermediate Similarity	NPC272029
0.8455	Intermediate Similarity	NPC232165
0.8454	Intermediate Similarity	NPC27974
0.8447	Intermediate Similarity	NPC80800
0.844	Intermediate Similarity	NPC162113
0.844	Intermediate Similarity	NPC62546
0.8431	Intermediate Similarity	NPC260775
0.8426	Intermediate Similarity	NPC151537
0.8426	Intermediate Similarity	NPC469912
0.8421	Intermediate Similarity	NPC39029
0.8407	Intermediate Similarity	NPC69006
0.84	Intermediate Similarity	NPC245187
0.84	Intermediate Similarity	NPC152415
0.8381	Intermediate Similarity	NPC117115
0.8365	Intermediate Similarity	NPC269212
0.8365	Intermediate Similarity	NPC315022
0.8365	Intermediate Similarity	NPC108497
0.8365	Intermediate Similarity	NPC168393
0.8364	Intermediate Similarity	NPC22610
0.8364	Intermediate Similarity	NPC276737
0.8351	Intermediate Similarity	NPC407
0.8351	Intermediate Similarity	NPC307235
0.835	Intermediate Similarity	NPC12931
0.835	Intermediate Similarity	NPC130103
0.835	Intermediate Similarity	NPC70677
0.835	Intermediate Similarity	NPC130756
0.8349	Intermediate Similarity	NPC228452
0.8349	Intermediate Similarity	NPC302371
0.8348	Intermediate Similarity	NPC77789
0.8348	Intermediate Similarity	NPC122175
0.8348	Intermediate Similarity	NPC18128
0.8333	Intermediate Similarity	NPC474073
0.8333	Intermediate Similarity	NPC475078
0.8333	Intermediate Similarity	NPC475018
0.8333	Intermediate Similarity	NPC242178
0.8319	Intermediate Similarity	NPC85895
0.8319	Intermediate Similarity	NPC137294
0.8317	Intermediate Similarity	NPC222146
0.8304	Intermediate Similarity	NPC320864
0.8304	Intermediate Similarity	NPC50521
0.8304	Intermediate Similarity	NPC221549
0.8304	Intermediate Similarity	NPC244816
0.8302	Intermediate Similarity	NPC164576
0.8302	Intermediate Similarity	NPC21594
0.83	Intermediate Similarity	NPC29373
0.83	Intermediate Similarity	NPC55903
0.8288	Intermediate Similarity	NPC53906
0.8286	Intermediate Similarity	NPC315936
0.8276	Intermediate Similarity	NPC96940
0.8265	Intermediate Similarity	NPC19680
0.8257	Intermediate Similarity	NPC54373
0.8257	Intermediate Similarity	NPC268032
0.8247	Intermediate Similarity	NPC155393
0.8246	Intermediate Similarity	NPC223451
0.8241	Intermediate Similarity	NPC473524
0.8224	Intermediate Similarity	NPC151477
0.8218	Intermediate Similarity	NPC76938
0.8214	Intermediate Similarity	NPC114064
0.8214	Intermediate Similarity	NPC141090
0.8214	Intermediate Similarity	NPC123559
0.8205	Intermediate Similarity	NPC174729
0.8205	Intermediate Similarity	NPC224342
0.8205	Intermediate Similarity	NPC139774
0.82	Intermediate Similarity	NPC306074
0.8182	Intermediate Similarity	NPC123273
0.8182	Intermediate Similarity	NPC318325

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 NPC227458 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	293
0.1-0.2	1073
0.2-0.3	1695
0.3-0.4	2981
0.4-0.5	1703
0.5-0.6	1030
0.6-0.7	324
0.7-0.8	43
0.8-0.85	4
0.85-0.9	1
0.9-0.95	3
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9505	High Similarity	NPD4750	Phase 3
0.9192	High Similarity	NPD846	Approved
0.9192	High Similarity	NPD940	Approved
0.9072	High Similarity	NPD844	Approved
0.8788	High Similarity	NPD288	Approved
0.8529	High Similarity	NPD1242	Phase 1
0.835	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.8276	Intermediate Similarity	NPD4749	Approved
0.8119	Intermediate Similarity	NPD845	Approved
0.8039	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.7961	Intermediate Similarity	NPD2860	Approved
0.7961	Intermediate Similarity	NPD1809	Phase 2
0.7961	Intermediate Similarity	NPD2859	Approved
0.7917	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7905	Intermediate Similarity	NPD3020	Approved
0.7869	Intermediate Similarity	NPD4625	Phase 3
0.7864	Intermediate Similarity	NPD2933	Approved
0.7864	Intermediate Similarity	NPD2934	Approved
0.7857	Intermediate Similarity	NPD7635	Approved
0.7812	Intermediate Similarity	NPD9093	Approved
0.7805	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7732	Intermediate Similarity	NPD9089	Approved
0.7727	Intermediate Similarity	NPD2342	Discontinued
0.7677	Intermediate Similarity	NPD111	Approved
0.7636	Intermediate Similarity	NPD1445	Approved
0.7636	Intermediate Similarity	NPD1444	Approved
0.7589	Intermediate Similarity	NPD3022	Approved
0.7589	Intermediate Similarity	NPD3021	Approved
0.75	Intermediate Similarity	NPD1610	Phase 2
0.75	Intermediate Similarity	NPD6671	Approved
0.7477	Intermediate Similarity	NPD9273	Approved
0.7458	Intermediate Similarity	NPD1548	Phase 1
0.7434	Intermediate Similarity	NPD1792	Phase 2
0.7419	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7385	Intermediate Similarity	NPD6099	Approved
0.7385	Intermediate Similarity	NPD6100	Approved
0.7364	Intermediate Similarity	NPD9500	Approved
0.736	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.736	Intermediate Similarity	NPD4908	Phase 1
0.7355	Intermediate Similarity	NPD422	Phase 1
0.7339	Intermediate Similarity	NPD599	Approved
0.7339	Intermediate Similarity	NPD859	Approved
0.7339	Intermediate Similarity	NPD858	Approved
0.7339	Intermediate Similarity	NPD602	Approved
0.7317	Intermediate Similarity	NPD6696	Suspended
0.7308	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7302	Intermediate Similarity	NPD3027	Phase 3
0.7282	Intermediate Similarity	NPD9094	Approved
0.7244	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7213	Intermediate Similarity	NPD1201	Approved
0.719	Intermediate Similarity	NPD4626	Approved
0.7167	Intermediate Similarity	NPD3091	Approved
0.7164	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7155	Intermediate Similarity	NPD228	Approved
0.7155	Intermediate Similarity	NPD6124	Clinical (unspecified phase)
0.7132	Intermediate Similarity	NPD1613	Approved
0.7132	Intermediate Similarity	NPD943	Approved
0.7132	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7119	Intermediate Similarity	NPD1791	Approved
0.7119	Intermediate Similarity	NPD1476	Clinical (unspecified phase)
0.7119	Intermediate Similarity	NPD1793	Approved
0.7119	Intermediate Similarity	NPD497	Approved
0.7073	Intermediate Similarity	NPD3092	Approved
0.7049	Intermediate Similarity	NPD4059	Approved
0.7049	Intermediate Similarity	NPD2932	Approved
0.7049	Intermediate Similarity	NPD1778	Approved
0.7049	Intermediate Similarity	NPD3019	Approved
0.7034	Intermediate Similarity	NPD2228	Approved
0.7034	Intermediate Similarity	NPD2234	Approved
0.7034	Intermediate Similarity	NPD498	Approved
0.7034	Intermediate Similarity	NPD2229	Approved
0.7034	Intermediate Similarity	NPD495	Approved
0.7034	Intermediate Similarity	NPD1398	Phase 1
0.7034	Intermediate Similarity	NPD496	Approved
0.7034	Intermediate Similarity	NPD7159	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD2226	Clinical (unspecified phase)
0.7023	Intermediate Similarity	NPD1607	Approved
0.7007	Intermediate Similarity	NPD7390	Discontinued
0.7	Intermediate Similarity	NPD7325	Clinical (unspecified phase)
0.6991	Remote Similarity	NPD9610	Approved
0.6991	Remote Similarity	NPD9608	Approved
0.6984	Remote Similarity	NPD1131	Approved
0.6984	Remote Similarity	NPD1470	Approved
0.6984	Remote Similarity	NPD1134	Approved
0.6984	Remote Similarity	NPD3094	Phase 2
0.6984	Remote Similarity	NPD1129	Approved
0.6984	Remote Similarity	NPD1135	Approved
0.6984	Remote Similarity	NPD1133	Approved
0.6983	Remote Similarity	NPD9380	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD9614	Approved
0.6975	Remote Similarity	NPD9618	Approved
0.696	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD290	Approved
0.6949	Remote Similarity	NPD9377	Approved
0.6949	Remote Similarity	NPD9379	Approved
0.6923	Remote Similarity	NPD9280	Clinical (unspecified phase)
0.6911	Remote Similarity	NPD1751	Approved
0.6911	Remote Similarity	NPD2286	Discontinued
0.6907	Remote Similarity	NPD9087	Approved
0.6897	Remote Similarity	NPD74	Approved
0.6897	Remote Similarity	NPD9266	Approved
0.6894	Remote Similarity	NPD2568	Approved
0.6885	Remote Similarity	NPD1759	Phase 1
0.688	Remote Similarity	NPD9269	Phase 2
0.6875	Remote Similarity	NPD3028	Approved
0.6875	Remote Similarity	NPD2861	Phase 2
0.6875	Remote Similarity	NPD3018	Phase 2
0.687	Remote Similarity	NPD1240	Approved
0.686	Remote Similarity	NPD405	Clinical (unspecified phase)
0.686	Remote Similarity	NPD7340	Approved
0.686	Remote Similarity	NPD9493	Approved
0.6855	Remote Similarity	NPD1983	Approved
0.6855	Remote Similarity	NPD1980	Approved
0.6855	Remote Similarity	NPD1981	Approved
0.685	Remote Similarity	NPD4339	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD9268	Approved
0.6829	Remote Similarity	NPD5691	Approved
0.6829	Remote Similarity	NPD4093	Discontinued
0.681	Remote Similarity	NPD9264	Approved
0.681	Remote Similarity	NPD9263	Approved
0.681	Remote Similarity	NPD9267	Approved
0.6803	Remote Similarity	NPD9613	Approved
0.6803	Remote Similarity	NPD16	Approved
0.6803	Remote Similarity	NPD9615	Approved
0.6803	Remote Similarity	NPD1758	Phase 1
0.6803	Remote Similarity	NPD856	Approved
0.6803	Remote Similarity	NPD9616	Approved
0.68	Remote Similarity	NPD5350	Clinical (unspecified phase)
0.68	Remote Similarity	NPD5351	Clinical (unspecified phase)
0.68	Remote Similarity	NPD9088	Approved
0.6791	Remote Similarity	NPD651	Clinical (unspecified phase)
0.6777	Remote Similarity	NPD709	Approved
0.6774	Remote Similarity	NPD9381	Approved
0.6774	Remote Similarity	NPD5238	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD4589	Approved
0.6774	Remote Similarity	NPD3095	Discontinued
0.6774	Remote Similarity	NPD9384	Approved
0.6767	Remote Similarity	NPD4097	Suspended
0.6765	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6752	Remote Similarity	NPD2684	Approved
0.6748	Remote Similarity	NPD316	Approved
0.6748	Remote Similarity	NPD7330	Discontinued
0.6748	Remote Similarity	NPD5304	Approved
0.6748	Remote Similarity	NPD5303	Approved
0.6746	Remote Similarity	NPD2233	Approved
0.6746	Remote Similarity	NPD2232	Approved
0.6746	Remote Similarity	NPD2230	Approved
0.6742	Remote Similarity	NPD1555	Discontinued
0.6742	Remote Similarity	NPD2238	Phase 2
0.6741	Remote Similarity	NPD5405	Approved
0.6741	Remote Similarity	NPD5408	Approved
0.6741	Remote Similarity	NPD5406	Approved
0.6741	Remote Similarity	NPD5404	Approved
0.6724	Remote Similarity	NPD968	Approved
0.672	Remote Similarity	NPD3496	Discontinued
0.6718	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.67	Remote Similarity	NPD9294	Approved
0.6694	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.6694	Remote Similarity	NPD4235	Clinical (unspecified phase)
0.6693	Remote Similarity	NPD1755	Approved
0.6693	Remote Similarity	NPD2982	Phase 2
0.6693	Remote Similarity	NPD9622	Approved
0.6693	Remote Similarity	NPD2983	Phase 2
0.6692	Remote Similarity	NPD600	Approved
0.6692	Remote Similarity	NPD230	Phase 1
0.6692	Remote Similarity	NPD596	Approved
0.6667	Remote Similarity	NPD1091	Approved
0.6667	Remote Similarity	NPD6405	Approved
0.6667	Remote Similarity	NPD6407	Approved
0.6667	Remote Similarity	NPD318	Approved
0.6667	Remote Similarity	NPD1510	Phase 2
0.6667	Remote Similarity	NPD317	Approved
0.6667	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.6639	Remote Similarity	NPD256	Approved
0.6639	Remote Similarity	NPD255	Approved
0.6618	Remote Similarity	NPD1551	Phase 2
0.6617	Remote Similarity	NPD468	Phase 1
0.6615	Remote Similarity	NPD5736	Approved
0.6614	Remote Similarity	NPD2981	Phase 2
0.6614	Remote Similarity	NPD1608	Approved
0.6612	Remote Similarity	NPD5283	Phase 1
0.6609	Remote Similarity	NPD5700	Clinical (unspecified phase)
0.6596	Remote Similarity	NPD2532	Approved
0.6596	Remote Similarity	NPD2534	Approved
0.6596	Remote Similarity	NPD2533	Approved
0.6589	Remote Similarity	NPD2797	Approved
0.6589	Remote Similarity	NPD1164	Approved
0.6587	Remote Similarity	NPD3143	Discontinued
0.6585	Remote Similarity	NPD7636	Approved
0.6579	Remote Similarity	NPD1616	Discontinued
0.6562	Remote Similarity	NPD4659	Approved
0.656	Remote Similarity	NPD1651	Approved
0.6557	Remote Similarity	NPD475	Phase 2
0.6552	Remote Similarity	NPD9244	Approved
0.6547	Remote Similarity	NPD3892	Phase 2
0.6544	Remote Similarity	NPD3299	Clinical (unspecified phase)
0.6541	Remote Similarity	NPD840	Approved
0.6541	Remote Similarity	NPD839	Approved
0.6538	Remote Similarity	NPD9621	Approved
0.6538	Remote Similarity	NPD2195	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