NPASS Compound

Structure

NPC246056 OpenBabel07101718252D 30 31 0 0 0 0 0 0 0 0999 V2000 2.5981 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -5.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -5.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 1.5000 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 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 1.5000 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 6.0622 0.5000 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 7.7942 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 2.0000 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 0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6603 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 0.5000 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 1 3 1 0 0 0 0 2 4 1 0 0 0 0 3 5 1 0 0 0 0 4 6 1 0 0 0 0 5 7 1 0 0 0 0 6 8 1 0 0 0 0 7 9 1 0 0 0 0 8 10 1 0 0 0 0 9 11 1 0 0 0 0 10 12 1 0 0 0 0 11 13 1 0 0 0 0 12 14 1 0 0 0 0 13 21 1 0 0 0 0 14 22 1 0 0 0 0 15 21 2 0 0 0 0 15 23 1 0 0 0 0 16 21 1 0 0 0 0 16 24 2 0 0 0 0 17 22 2 0 0 0 0 17 25 1 0 0 0 0 18 22 1 0 0 0 0 18 26 2 0 0 0 0 19 23 2 0 0 0 0 19 24 1 0 0 0 0 20 25 2 0 0 0 0 20 26 1 0 0 0 0 23 27 1 0 0 0 0 24 28 1 0 0 0 0 25 29 1 0 0 0 0 26 30 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	414.28
Volume:	460.481
LogP:	7.641
LogD:	4.541
LogS:	-2.895
# Rotatable Bonds:	15
TPSA:	80.92
# H-Bond Aceptor:	4
# H-Bond Donor:	4
# Rings:	2
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.237
Synthetic Accessibility Score:	2.015
Fsp3:	0.538
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.342
MDCK Permeability:	1.4695773643325083e-05
Pgp-inhibitor:	0.004
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.02
20% Bioavailability (F20%):	1.0
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.022
Plasma Protein Binding (PPB):	99.59068298339844%
Volume Distribution (VD):	1.733
Pgp-substrate:	0.9048455357551575%

ADMET: Metabolism

CYP1A2-inhibitor:	0.829
CYP1A2-substrate:	0.164
CYP2C19-inhibitor:	0.927
CYP2C19-substrate:	0.054
CYP2C9-inhibitor:	0.311
CYP2C9-substrate:	0.993
CYP2D6-inhibitor:	0.976
CYP2D6-substrate:	0.344
CYP3A4-inhibitor:	0.623
CYP3A4-substrate:	0.058

ADMET: Excretion

Clearance (CL):	8.575
Half-life (T1/2):	0.819

ADMET: Toxicity

hERG Blockers:	0.333
Human Hepatotoxicity (H-HT):	0.113
Drug-inuced Liver Injury (DILI):	0.013
AMES Toxicity:	0.057
Rat Oral Acute Toxicity:	0.042
Maximum Recommended Daily Dose:	0.934
Skin Sensitization:	0.98
Carcinogencity:	0.017
Eye Corrosion:	0.888
Eye Irritation:	0.945
Respiratory Toxicity:	0.595

Download Data

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

Natural Product: NPC246056

Natural Product ID:	NPC246056
*Common Name:**	Bisnorstriatol
IUPAC Name:	5-[14-(3,5-dihydroxyphenyl)tetradecyl]benzene-1,3-diol
Synonyms:	Bisnorstriatol
Standard InCHIKey:	QUXULJDSRDXUCR-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C26H38O4/c27-23-15-21(16-24(28)19-23)13-11-9-7-5-3-1-2-4-6-8-10-12-14-22-17-25(29)20-26(30)18-22/h15-20,27-30H,1-14H2
SMILES:	C(CCCCCCCc1cc(cc(c1)O)O)CCCCCCc1cc(cc(c1)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL426392
PubChem CID:	10431955
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
NPO8932	Panopsis rubescens	Species	Proteaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10096862]
NPO8945	Grevillea robusta	Species	Proteaceae	Eukaryota	leaves	n.a.	n.a.	PMID[17243726]
NPO8945	Grevillea robusta	Species	Proteaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8945	Grevillea robusta	Species	Proteaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8945	Grevillea robusta	Species	Proteaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO8945	Grevillea robusta	Species	Proteaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8932	Panopsis rubescens	Species	Proteaceae	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
IC50	4
Others	2

Activity Type	# Activity
Cell Line	3
Individual Protein	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	29200.0	nM	PMID[506865]
NPT397	Cell Line	NCI-H460	Homo sapiens	IC50	=	28800.0	nM	PMID[506865]
NPT395	Cell Line	SF-268	Homo sapiens	IC50	=	29800.0	nM	PMID[506865]
NPT2216	Individual Protein	DNA polymerase beta	Rattus norvegicus	Inhibition	=	79.0	%	PMID[506866]
NPT2216	Individual Protein	DNA polymerase beta	Rattus norvegicus	Inhibition	=	50.0	%	PMID[506866]
NPT2216	Individual Protein	DNA polymerase beta	Rattus norvegicus	IC50	=	5800.0	nM	PMID[506866]

☑ 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 NPC246056 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	295
0.1-0.2	1597
0.2-0.3	4945
0.3-0.4	14256
0.4-0.5	4905
0.5-0.6	7999
0.6-0.7	6598
0.7-0.8	1795
0.8-0.85	169
0.85-0.9	70
0.9-0.95	56
0.95-1	12

Similarity Score	Similarity Level	Natural Product ID
0.9898	High Similarity	NPC302681
0.9898	High Similarity	NPC39097
0.9898	High Similarity	NPC39664
0.9898	High Similarity	NPC109691
0.9898	High Similarity	NPC118286
0.9898	High Similarity	NPC470700
0.9798	High Similarity	NPC54844
0.9796	High Similarity	NPC134829
0.9694	High Similarity	NPC241891
0.949	High Similarity	NPC72947
0.949	High Similarity	NPC166313
0.949	High Similarity	NPC100340
0.949	High Similarity	NPC137415
0.949	High Similarity	NPC284011
0.949	High Similarity	NPC143659
0.949	High Similarity	NPC11280
0.949	High Similarity	NPC147310
0.949	High Similarity	NPC24407
0.949	High Similarity	NPC294186
0.949	High Similarity	NPC192032
0.9394	High Similarity	NPC222522
0.9394	High Similarity	NPC94351
0.9394	High Similarity	NPC85479
0.9394	High Similarity	NPC106396
0.9394	High Similarity	NPC168303
0.9394	High Similarity	NPC71002
0.9394	High Similarity	NPC302219
0.9394	High Similarity	NPC53051
0.9394	High Similarity	NPC24404
0.9394	High Similarity	NPC242342
0.9394	High Similarity	NPC146798
0.9394	High Similarity	NPC313030
0.9394	High Similarity	NPC249828
0.9388	High Similarity	NPC10588
0.93	High Similarity	NPC30506
0.93	High Similarity	NPC102216
0.9238	High Similarity	NPC23804
0.9223	High Similarity	NPC33728
0.9223	High Similarity	NPC19808
0.9192	High Similarity	NPC166761
0.9184	High Similarity	NPC291789
0.9143	High Similarity	NPC43525
0.9143	High Similarity	NPC166995
0.9126	High Similarity	NPC174981
0.9118	High Similarity	NPC12640
0.9118	High Similarity	NPC201662
0.9118	High Similarity	NPC99836
0.9057	High Similarity	NPC261343
0.9048	High Similarity	NPC476632
0.9048	High Similarity	NPC224527
0.9048	High Similarity	NPC165770
0.9048	High Similarity	NPC4493
0.9048	High Similarity	NPC225679
0.9029	High Similarity	NPC61033
0.9029	High Similarity	NPC305603
0.9029	High Similarity	NPC232523
0.9029	High Similarity	NPC204901
0.9029	High Similarity	NPC158253
0.902	High Similarity	NPC37802
0.902	High Similarity	NPC292452
0.902	High Similarity	NPC474839
0.9	High Similarity	NPC275053
0.9	High Similarity	NPC248573
0.9	High Similarity	NPC161571
0.8981	High Similarity	NPC115808
0.8981	High Similarity	NPC114064
0.898	High Similarity	NPC32714
0.8922	High Similarity	NPC119860
0.8922	High Similarity	NPC227458
0.8922	High Similarity	NPC244513
0.8922	High Similarity	NPC218879
0.8899	High Similarity	NPC470760
0.8899	High Similarity	NPC127894
0.8899	High Similarity	NPC15860
0.8899	High Similarity	NPC219070
0.8899	High Similarity	NPC470759
0.8879	High Similarity	NPC117846
0.8878	High Similarity	NPC76938
0.8868	High Similarity	NPC268032
0.8857	High Similarity	NPC186385
0.8857	High Similarity	NPC299568
0.8818	High Similarity	NPC9592
0.8818	High Similarity	NPC48781
0.8796	High Similarity	NPC107240
0.8776	High Similarity	NPC295295
0.8774	High Similarity	NPC475018
0.8762	High Similarity	NPC63698
0.8762	High Similarity	NPC61885
0.875	High Similarity	NPC248904
0.8727	High Similarity	NPC277588
0.8716	High Similarity	NPC53906
0.8716	High Similarity	NPC246760
0.8716	High Similarity	NPC84999
0.8679	High Similarity	NPC202647
0.8649	High Similarity	NPC144343
0.8641	High Similarity	NPC315022
0.8627	High Similarity	NPC294741
0.8624	High Similarity	NPC276737
0.8624	High Similarity	NPC22610
0.86	High Similarity	NPC274678
0.8586	High Similarity	NPC147284
0.8586	High Similarity	NPC306884
0.8586	High Similarity	NPC3358
0.8586	High Similarity	NPC162314
0.8586	High Similarity	NPC210497
0.8586	High Similarity	NPC94139
0.8585	High Similarity	NPC105727
0.8585	High Similarity	NPC58427
0.8585	High Similarity	NPC114392
0.8585	High Similarity	NPC34864
0.8584	High Similarity	NPC24125
0.8571	High Similarity	NPC191866
0.8571	High Similarity	NPC192
0.8571	High Similarity	NPC217174
0.8559	High Similarity	NPC33270
0.8559	High Similarity	NPC69261
0.8559	High Similarity	NPC474933
0.8558	High Similarity	NPC323810
0.8558	High Similarity	NPC315936
0.8545	High Similarity	NPC472893
0.8545	High Similarity	NPC808
0.8532	High Similarity	NPC263753
0.8532	High Similarity	NPC62546
0.8532	High Similarity	NPC162113
0.8532	High Similarity	NPC319803
0.8509	High Similarity	NPC237667
0.8509	High Similarity	NPC39029
0.85	High Similarity	NPC151715
0.8496	Intermediate Similarity	NPC223451
0.8496	Intermediate Similarity	NPC69006
0.8491	Intermediate Similarity	NPC176527
0.8482	Intermediate Similarity	NPC190514
0.8482	Intermediate Similarity	NPC206
0.8468	Intermediate Similarity	NPC123559
0.8468	Intermediate Similarity	NPC150624
0.8468	Intermediate Similarity	NPC141090
0.8462	Intermediate Similarity	NPC168393
0.8435	Intermediate Similarity	NPC122175
0.8426	Intermediate Similarity	NPC168657
0.8426	Intermediate Similarity	NPC242178
0.8416	Intermediate Similarity	NPC26244
0.8407	Intermediate Similarity	NPC184302
0.8378	Intermediate Similarity	NPC167934
0.8365	Intermediate Similarity	NPC7686
0.8365	Intermediate Similarity	NPC91461
0.8365	Intermediate Similarity	NPC40258
0.8362	Intermediate Similarity	NPC53567
0.835	Intermediate Similarity	NPC80027
0.8348	Intermediate Similarity	NPC476633
0.8333	Intermediate Similarity	NPC82664
0.8333	Intermediate Similarity	NPC473388
0.8333	Intermediate Similarity	NPC216520
0.8333	Intermediate Similarity	NPC132271
0.8333	Intermediate Similarity	NPC292730
0.83	Intermediate Similarity	NPC45040
0.8291	Intermediate Similarity	NPC140521
0.8291	Intermediate Similarity	NPC139774
0.8291	Intermediate Similarity	NPC78446
0.8291	Intermediate Similarity	NPC174729
0.8288	Intermediate Similarity	NPC228287
0.8288	Intermediate Similarity	NPC180508
0.8276	Intermediate Similarity	NPC120172
0.8276	Intermediate Similarity	NPC18128
0.8276	Intermediate Similarity	NPC77789
0.8273	Intermediate Similarity	NPC473521
0.8269	Intermediate Similarity	NPC213730
0.8269	Intermediate Similarity	NPC129373
0.8269	Intermediate Similarity	NPC48730
0.8269	Intermediate Similarity	NPC248396
0.8257	Intermediate Similarity	NPC94045
0.8257	Intermediate Similarity	NPC224870
0.8257	Intermediate Similarity	NPC2682
0.823	Intermediate Similarity	NPC221549
0.823	Intermediate Similarity	NPC50521
0.823	Intermediate Similarity	NPC195466
0.823	Intermediate Similarity	NPC244816
0.8224	Intermediate Similarity	NPC67250
0.8224	Intermediate Similarity	NPC469913
0.822	Intermediate Similarity	NPC249836
0.8214	Intermediate Similarity	NPC232165
0.8208	Intermediate Similarity	NPC471511
0.8205	Intermediate Similarity	NPC136319
0.8205	Intermediate Similarity	NPC233526
0.8205	Intermediate Similarity	NPC282496
0.819	Intermediate Similarity	NPC12221
0.819	Intermediate Similarity	NPC477685
0.8182	Intermediate Similarity	NPC257430
0.8182	Intermediate Similarity	NPC179002
0.8182	Intermediate Similarity	NPC296920
0.8182	Intermediate Similarity	NPC187583
0.8182	Intermediate Similarity	NPC27974
0.8182	Intermediate Similarity	NPC255068
0.8182	Intermediate Similarity	NPC90520
0.8174	Intermediate Similarity	NPC472071
0.8173	Intermediate Similarity	NPC51333
0.8173	Intermediate Similarity	NPC132078
0.8173	Intermediate Similarity	NPC260775
0.8173	Intermediate Similarity	NPC78119
0.8173	Intermediate Similarity	NPC216468
0.8173	Intermediate Similarity	NPC92730

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 NPC246056 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	274
0.1-0.2	985
0.2-0.3	1431
0.3-0.4	2965
0.4-0.5	1889
0.5-0.6	1129
0.6-0.7	418
0.7-0.8	48
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
0.9	High Similarity	NPD1242	Phase 1
0.8857	High Similarity	NPD4750	Phase 3
0.8544	High Similarity	NPD846	Approved
0.8544	High Similarity	NPD940	Approved
0.8416	Intermediate Similarity	NPD2860	Approved
0.8416	Intermediate Similarity	NPD2859	Approved
0.835	Intermediate Similarity	NPD3020	Approved
0.8317	Intermediate Similarity	NPD2933	Approved
0.8317	Intermediate Similarity	NPD2934	Approved
0.8165	Intermediate Similarity	NPD3021	Approved
0.8165	Intermediate Similarity	NPD3022	Approved
0.8058	Intermediate Similarity	NPD844	Approved
0.781	Intermediate Similarity	NPD288	Approved
0.7805	Intermediate Similarity	NPD3027	Phase 3
0.7788	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.7788	Intermediate Similarity	NPD7635	Approved
0.7757	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.775	Intermediate Similarity	NPD4749	Approved
0.7732	Intermediate Similarity	NPD9093	Approved
0.7661	Intermediate Similarity	NPD4625	Phase 3
0.7658	Intermediate Similarity	NPD2342	Discontinued
0.7653	Intermediate Similarity	NPD9089	Approved
0.7642	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7583	Intermediate Similarity	NPD1610	Phase 2
0.7581	Intermediate Similarity	NPD4908	Phase 1
0.7581	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7561	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7542	Intermediate Similarity	NPD1548	Phase 1
0.7524	Intermediate Similarity	NPD845	Approved
0.7522	Intermediate Similarity	NPD1792	Phase 2
0.746	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.746	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7436	Intermediate Similarity	NPD6671	Approved
0.7431	Intermediate Similarity	NPD3028	Approved
0.7426	Intermediate Similarity	NPD111	Approved
0.7411	Intermediate Similarity	NPD1445	Approved
0.7411	Intermediate Similarity	NPD1444	Approved
0.7383	Intermediate Similarity	NPD1809	Phase 2
0.7364	Intermediate Similarity	NPD2568	Approved
0.7344	Intermediate Similarity	NPD1613	Approved
0.7344	Intermediate Similarity	NPD943	Approved
0.7344	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7339	Intermediate Similarity	NPD4339	Clinical (unspecified phase)
0.7265	Intermediate Similarity	NPD2228	Approved
0.7265	Intermediate Similarity	NPD2229	Approved
0.7265	Intermediate Similarity	NPD2234	Approved
0.725	Intermediate Similarity	NPD3091	Approved
0.7212	Intermediate Similarity	NPD9094	Approved
0.7203	Intermediate Similarity	NPD1476	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD3094	Phase 2
0.7197	Intermediate Similarity	NPD6100	Approved
0.7197	Intermediate Similarity	NPD6099	Approved
0.719	Intermediate Similarity	NPD4093	Discontinued
0.7177	Intermediate Similarity	NPD2982	Phase 2
0.7177	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7177	Intermediate Similarity	NPD2983	Phase 2
0.7154	Intermediate Similarity	NPD3092	Approved
0.7154	Intermediate Similarity	NPD1201	Approved
0.7154	Intermediate Similarity	NPD5350	Clinical (unspecified phase)
0.7154	Intermediate Similarity	NPD5351	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD9500	Approved
0.7143	Intermediate Similarity	NPD602	Approved
0.7143	Intermediate Similarity	NPD859	Approved
0.7143	Intermediate Similarity	NPD858	Approved
0.7143	Intermediate Similarity	NPD599	Approved
0.7132	Intermediate Similarity	NPD6407	Approved
0.7132	Intermediate Similarity	NPD6405	Approved
0.7131	Intermediate Similarity	NPD2286	Discontinued
0.7131	Intermediate Similarity	NPD2932	Approved
0.7131	Intermediate Similarity	NPD4059	Approved
0.7131	Intermediate Similarity	NPD3019	Approved
0.7131	Intermediate Similarity	NPD5238	Clinical (unspecified phase)
0.7121	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7119	Intermediate Similarity	NPD5283	Phase 1
0.7105	Intermediate Similarity	NPD968	Approved
0.7097	Intermediate Similarity	NPD2981	Phase 2
0.7094	Intermediate Similarity	NPD6124	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD9273	Approved
0.7087	Intermediate Similarity	NPD3018	Phase 2
0.7087	Intermediate Similarity	NPD2861	Phase 2
0.7083	Intermediate Similarity	NPD7325	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD1470	Approved
0.7054	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7016	Intermediate Similarity	NPD422	Phase 1
0.7009	Intermediate Similarity	NPD9280	Clinical (unspecified phase)
0.6992	Remote Similarity	NPD3095	Discontinued
0.6985	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6984	Remote Similarity	NPD5311	Approved
0.6984	Remote Similarity	NPD5310	Approved
0.6975	Remote Similarity	NPD7159	Clinical (unspecified phase)
0.6967	Remote Similarity	NPD2226	Clinical (unspecified phase)
0.6967	Remote Similarity	NPD7330	Discontinued
0.696	Remote Similarity	NPD9269	Phase 2
0.6957	Remote Similarity	NPD7390	Discontinued
0.6949	Remote Similarity	NPD228	Approved
0.6923	Remote Similarity	NPD9380	Clinical (unspecified phase)
0.6917	Remote Similarity	NPD1791	Approved
0.6917	Remote Similarity	NPD497	Approved
0.6917	Remote Similarity	NPD1793	Approved
0.6911	Remote Similarity	NPD9268	Approved
0.6905	Remote Similarity	NPD4659	Approved
0.6891	Remote Similarity	NPD9379	Approved
0.6891	Remote Similarity	NPD9377	Approved
0.6875	Remote Similarity	NPD6584	Phase 3
0.6866	Remote Similarity	NPD1510	Phase 2
0.6861	Remote Similarity	NPD3892	Phase 2
0.6855	Remote Similarity	NPD4589	Approved
0.6855	Remote Similarity	NPD1751	Approved
0.685	Remote Similarity	NPD6696	Suspended
0.6842	Remote Similarity	NPD5314	Approved
0.6837	Remote Similarity	NPD9087	Approved
0.6833	Remote Similarity	NPD495	Approved
0.6833	Remote Similarity	NPD496	Approved
0.6833	Remote Similarity	NPD498	Approved
0.6829	Remote Similarity	NPD5303	Approved
0.6829	Remote Similarity	NPD5304	Approved
0.6825	Remote Similarity	NPD2562	Approved
0.6825	Remote Similarity	NPD2561	Approved
0.6825	Remote Similarity	NPD1608	Approved
0.6825	Remote Similarity	NPD2230	Approved
0.6825	Remote Similarity	NPD2233	Approved
0.6825	Remote Similarity	NPD2232	Approved
0.6822	Remote Similarity	NPD5736	Approved
0.6818	Remote Similarity	NPD2238	Phase 2
0.6818	Remote Similarity	NPD3061	Approved
0.6818	Remote Similarity	NPD6346	Approved
0.6818	Remote Similarity	NPD1240	Approved
0.6818	Remote Similarity	NPD1555	Discontinued
0.6818	Remote Similarity	NPD3062	Approved
0.6818	Remote Similarity	NPD3059	Approved
0.6815	Remote Similarity	NPD5408	Approved
0.6815	Remote Similarity	NPD5406	Approved
0.6815	Remote Similarity	NPD5405	Approved
0.6815	Remote Similarity	NPD5404	Approved
0.68	Remote Similarity	NPD1983	Approved
0.68	Remote Similarity	NPD1981	Approved
0.68	Remote Similarity	NPD1980	Approved
0.6797	Remote Similarity	NPD4104	Clinical (unspecified phase)
0.6797	Remote Similarity	NPD4103	Phase 2
0.6797	Remote Similarity	NPD3053	Approved
0.6797	Remote Similarity	NPD3055	Approved
0.6786	Remote Similarity	NPD7447	Phase 1
0.6783	Remote Similarity	NPD9608	Approved
0.6783	Remote Similarity	NPD9610	Approved
0.678	Remote Similarity	NPD5451	Approved
0.6777	Remote Similarity	NPD9618	Approved
0.6777	Remote Similarity	NPD9614	Approved
0.6772	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD7266	Discontinued
0.675	Remote Similarity	NPD7843	Approved
0.675	Remote Similarity	NPD5535	Approved
0.6739	Remote Similarity	NPD3750	Approved
0.6733	Remote Similarity	NPD9088	Approved
0.6721	Remote Similarity	NPD7157	Approved
0.6721	Remote Similarity	NPD709	Approved
0.672	Remote Similarity	NPD9384	Approved
0.672	Remote Similarity	NPD9381	Approved
0.6718	Remote Similarity	NPD7095	Approved
0.6716	Remote Similarity	NPD1607	Approved
0.6696	Remote Similarity	NPD5700	Clinical (unspecified phase)
0.6695	Remote Similarity	NPD2684	Approved
0.6694	Remote Similarity	NPD7741	Discontinued
0.6694	Remote Similarity	NPD1759	Phase 1
0.6693	Remote Similarity	NPD2235	Phase 2
0.6693	Remote Similarity	NPD2231	Phase 2
0.6692	Remote Similarity	NPD4060	Phase 1
0.6691	Remote Similarity	NPD2935	Discontinued
0.6667	Remote Similarity	NPD3026	Approved
0.6667	Remote Similarity	NPD3764	Approved
0.6667	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD2797	Approved
0.6667	Remote Similarity	NPD3847	Discontinued
0.6667	Remote Similarity	NPD4978	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD2028	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD1164	Approved
0.6667	Remote Similarity	NPD3023	Approved
0.6667	Remote Similarity	NPD405	Clinical (unspecified phase)
0.6642	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6642	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6642	Remote Similarity	NPD230	Phase 1
0.6641	Remote Similarity	NPD6583	Phase 3
0.6641	Remote Similarity	NPD6582	Phase 2
0.6641	Remote Similarity	NPD1755	Approved
0.664	Remote Similarity	NPD3025	Approved
0.664	Remote Similarity	NPD3024	Approved
0.6634	Remote Similarity	NPD9294	Approved
0.6618	Remote Similarity	NPD651	Clinical (unspecified phase)
0.6618	Remote Similarity	NPD3299	Clinical (unspecified phase)
0.6617	Remote Similarity	NPD6663	Approved
0.6615	Remote Similarity	NPD2195	Approved
0.6615	Remote Similarity	NPD7451	Discontinued
0.6615	Remote Similarity	NPD2194	Approved
0.6614	Remote Similarity	NPD1091	Approved
0.6613	Remote Similarity	NPD9615	Approved
0.6613	Remote Similarity	NPD856	Approved
0.6613	Remote Similarity	NPD1758	Phase 1
0.6613	Remote Similarity	NPD16	Approved
0.6613	Remote Similarity	NPD9613	Approved
0.6613	Remote Similarity	NPD9616	Approved
0.661	Remote Similarity	NPD9265	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