NPASS Compound

Structure

CID61885 OpenBabel06191715402D 23 24 0 0 0 0 0 0 0 0999 V2000 2.5981 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 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 1.7321 -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 -1.5000 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 -6.9282 -1.0000 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 -0.8660 -1.5000 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 2.5981 -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 -5.1962 -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 -6.9282 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 -5.1962 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 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 -4.3301 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 14 1 0 0 0 0 2 14 1 0 0 0 0 3 4 1 0 0 0 0 3 5 1 0 0 0 0 4 15 1 0 0 0 0 5 16 1 0 0 0 0 6 8 1 0 0 0 0 6 14 2 0 0 0 0 7 11 2 0 0 0 0 7 15 1 0 0 0 0 8 17 1 0 0 0 0 9 10 2 0 0 0 0 9 16 1 0 0 0 0 10 18 1 0 0 0 0 11 19 1 0 0 0 0 12 15 2 0 0 0 0 12 17 1 0 0 0 0 13 18 2 0 0 0 0 13 20 1 0 0 0 0 16 20 2 0 0 0 0 17 19 2 0 0 0 0 18 21 1 0 0 0 0 19 22 1 0 0 0 0 20 23 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	312.17
Volume:	345.279
LogP:	4.961
LogD:	3.994
LogS:	-3.33
# Rotatable Bonds:	6
TPSA:	60.69
# H-Bond Aceptor:	3
# H-Bond Donor:	3
# Rings:	2
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.689
Synthetic Accessibility Score:	2.41
Fsp3:	0.3
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:	-4.882
MDCK Permeability:	2.2927002646611072e-05
Pgp-inhibitor:	0.458
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.996
30% Bioavailability (F30%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.055
Plasma Protein Binding (PPB):	99.44361114501953%
Volume Distribution (VD):	1.565
Pgp-substrate:	0.9211562871932983%

ADMET: Metabolism

CYP1A2-inhibitor:	0.971
CYP1A2-substrate:	0.331
CYP2C19-inhibitor:	0.959
CYP2C19-substrate:	0.063
CYP2C9-inhibitor:	0.793
CYP2C9-substrate:	0.96
CYP2D6-inhibitor:	0.967
CYP2D6-substrate:	0.907
CYP3A4-inhibitor:	0.568
CYP3A4-substrate:	0.252

ADMET: Excretion

Clearance (CL):	17.658
Half-life (T1/2):	0.858

ADMET: Toxicity

hERG Blockers:	0.031
Human Hepatotoxicity (H-HT):	0.221
Drug-inuced Liver Injury (DILI):	0.023
AMES Toxicity:	0.147
Rat Oral Acute Toxicity:	0.116
Maximum Recommended Daily Dose:	0.526
Skin Sensitization:	0.955
Carcinogencity:	0.067
Eye Corrosion:	0.021
Eye Irritation:	0.945
Respiratory Toxicity:	0.129

Download Data

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

Natural Product: NPC61885

Natural Product ID:	NPC61885
*Common Name:**	Broussonin C
IUPAC Name:	4-[3-[4-hydroxy-3-(3-methylbut-2-enyl)phenyl]propyl]benzene-1,3-diol
Synonyms:	Broussonin C
Standard InCHIKey:	CMOZGCJOTGLPKO-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C20H24O3/c1-14(2)6-8-17-12-15(7-11-19(17)22)4-3-5-16-9-10-18(21)13-20(16)23/h6-7,9-13,21-23H,3-5,8H2,1-2H3
SMILES:	CC(=CCc1cc(CCCc2ccc(cc2O)O)ccc1O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL468906
PubChem CID:	442289
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0003467] Linear 1,3-diarylpropanoids [CHEMONTID:0003496] Cinnamylphenols

*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
NPO5495	Broussonetia papyrifera	Species	Moraceae	Eukaryota	n.a.	root	n.a.	PMID[11395279]
NPO16111	Broussonetia kazinoki	Species	Moraceae	Eukaryota	Leaves	n.a.	n.a.	PMID[11575957]
NPO5495	Broussonetia papyrifera	Species	Moraceae	Eukaryota	whole plants	Shawnee National Forest, Harrisburg, IL, US	n.a.	PMID[11678652]
NPO5495	Broussonetia papyrifera	Species	Moraceae	Eukaryota	whole plants	n.a.	n.a.	PMID[11678652]
NPO5495	Broussonetia papyrifera	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12419367]
NPO5495	Broussonetia papyrifera	Species	Moraceae	Eukaryota	leaves	Kaohsiung, Taiwan	2006-SEP	PMID[18986201]
NPO16111	Broussonetia kazinoki	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19046886]
NPO5495	Broussonetia papyrifera	Species	Moraceae	Eukaryota	Fruits	n.a.	n.a.	PMID[19296617]
NPO16111	Broussonetia kazinoki	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20493686]
NPO5495	Broussonetia papyrifera	Species	Moraceae	Eukaryota	n.a.	formosan	n.a.	PMID[8864236]
NPO5495	Broussonetia papyrifera	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9358644]
NPO16111	Broussonetia kazinoki	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9917310]
NPO5495	Broussonetia papyrifera	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO16111	Broussonetia kazinoki	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5495	Broussonetia papyrifera	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5495	Broussonetia papyrifera	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO16111	Broussonetia kazinoki	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO5495	Broussonetia papyrifera	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO5495	Broussonetia papyrifera	Species	Moraceae	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	2
Ki	3

Activity Type	# Activity
Individual Protein	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT43	Individual Protein	Tyrosinase	Agaricus bisporus	IC50	=	430.0	nM	PMID[483038]
NPT43	Individual Protein	Tyrosinase	Agaricus bisporus	Ki	=	230.0	nM	PMID[483038]
NPT43	Individual Protein	Tyrosinase	Agaricus bisporus	IC50	=	570.0	nM	PMID[483038]
NPT43	Individual Protein	Tyrosinase	Agaricus bisporus	Ki	=	290.0	nM	PMID[483038]
NPT43	Individual Protein	Tyrosinase	Agaricus bisporus	Ki	=	48.5	nM	PMID[483038]

☑ 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 NPC61885 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	293
0.1-0.2	1704
0.2-0.3	4919
0.3-0.4	14160
0.4-0.5	4809
0.5-0.6	7146
0.6-0.7	6977
0.7-0.8	2258
0.8-0.85	295
0.85-0.9	111
0.9-0.95	14
0.95-1	11

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC63698
0.9709	High Similarity	NPC4493
0.9709	High Similarity	NPC476632
0.9709	High Similarity	NPC225679
0.9709	High Similarity	NPC165770
0.97	High Similarity	NPC474839
0.9615	High Similarity	NPC43525
0.96	High Similarity	NPC119860
0.9524	High Similarity	NPC117846
0.9434	High Similarity	NPC107240
0.9245	High Similarity	NPC166995
0.9238	High Similarity	NPC475018
0.9223	High Similarity	NPC248904
0.92	High Similarity	NPC80027
0.9143	High Similarity	NPC19808
0.9143	High Similarity	NPC33728
0.9091	High Similarity	NPC131118
0.9048	High Similarity	NPC174981
0.9029	High Similarity	NPC241891
0.9029	High Similarity	NPC30506
0.9029	High Similarity	NPC102216
0.9	High Similarity	NPC277588
0.8972	High Similarity	NPC224527
0.8942	High Similarity	NPC99557
0.8942	High Similarity	NPC219286
0.8942	High Similarity	NPC134829
0.8942	High Similarity	NPC138942
0.8942	High Similarity	NPC292452
0.8932	High Similarity	NPC168829
0.8929	High Similarity	NPC223451
0.8909	High Similarity	NPC229147
0.8909	High Similarity	NPC85292
0.8909	High Similarity	NPC54507
0.89	High Similarity	NPC26244
0.8857	High Similarity	NPC109691
0.8857	High Similarity	NPC39664
0.8857	High Similarity	NPC470700
0.8857	High Similarity	NPC302681
0.8857	High Similarity	NPC118286
0.8857	High Similarity	NPC39097
0.885	High Similarity	NPC24125
0.8846	High Similarity	NPC288411
0.8839	High Similarity	NPC191866
0.8835	High Similarity	NPC143659
0.8835	High Similarity	NPC100340
0.8818	High Similarity	NPC84999
0.8818	High Similarity	NPC246760
0.8818	High Similarity	NPC464
0.8818	High Similarity	NPC185541
0.8812	High Similarity	NPC473388
0.8807	High Similarity	NPC263753
0.88	High Similarity	NPC128062
0.88	High Similarity	NPC151715
0.8785	High Similarity	NPC202647
0.8774	High Similarity	NPC232523
0.8774	High Similarity	NPC158253
0.8774	High Similarity	NPC204901
0.8774	High Similarity	NPC54844
0.8772	High Similarity	NPC476633
0.8772	High Similarity	NPC237667
0.8762	High Similarity	NPC37802
0.8762	High Similarity	NPC246056
0.875	High Similarity	NPC71002
0.875	High Similarity	NPC144343
0.875	High Similarity	NPC222522
0.875	High Similarity	NPC106396
0.875	High Similarity	NPC168303
0.875	High Similarity	NPC249828
0.875	High Similarity	NPC302219
0.875	High Similarity	NPC146798
0.875	High Similarity	NPC53051
0.875	High Similarity	NPC85479
0.875	High Similarity	NPC94351
0.875	High Similarity	NPC313030
0.875	High Similarity	NPC242342
0.875	High Similarity	NPC24404
0.8738	High Similarity	NPC248573
0.8738	High Similarity	NPC166761
0.8738	High Similarity	NPC10588
0.8738	High Similarity	NPC161571
0.8738	High Similarity	NPC275053
0.8704	High Similarity	NPC224870
0.8679	High Similarity	NPC201662
0.8679	High Similarity	NPC271274
0.8679	High Similarity	NPC12640
0.8679	High Similarity	NPC99836
0.8667	High Similarity	NPC227458
0.8667	High Similarity	NPC218879
0.8667	High Similarity	NPC244513
0.8661	High Similarity	NPC470760
0.8654	High Similarity	NPC166313
0.8654	High Similarity	NPC11280
0.8654	High Similarity	NPC284011
0.8654	High Similarity	NPC137415
0.8654	High Similarity	NPC294186
0.8654	High Similarity	NPC192032
0.8654	High Similarity	NPC24407
0.8654	High Similarity	NPC72947
0.8654	High Similarity	NPC147310
0.8641	High Similarity	NPC128723
0.8636	High Similarity	NPC23804
0.8636	High Similarity	NPC261343
0.8621	High Similarity	NPC53567
0.8611	High Similarity	NPC299568
0.8611	High Similarity	NPC186385
0.86	High Similarity	NPC45040
0.86	High Similarity	NPC204210
0.8571	High Similarity	NPC115808
0.8559	High Similarity	NPC12656
0.8559	High Similarity	NPC473137
0.8558	High Similarity	NPC213730
0.8558	High Similarity	NPC225506
0.8547	High Similarity	NPC197351
0.8547	High Similarity	NPC106914
0.8547	High Similarity	NPC246648
0.8547	High Similarity	NPC134195
0.8547	High Similarity	NPC86502
0.8544	High Similarity	NPC77492
0.8544	High Similarity	NPC291789
0.8532	High Similarity	NPC296683
0.8529	High Similarity	NPC8392
0.8519	High Similarity	NPC262365
0.8519	High Similarity	NPC95344
0.8509	High Similarity	NPC217174
0.8496	Intermediate Similarity	NPC33270
0.8496	Intermediate Similarity	NPC69261
0.8496	Intermediate Similarity	NPC474933
0.8482	Intermediate Similarity	NPC808
0.8476	Intermediate Similarity	NPC40258
0.8476	Intermediate Similarity	NPC51015
0.8476	Intermediate Similarity	NPC91461
0.8476	Intermediate Similarity	NPC7686
0.8475	Intermediate Similarity	NPC285040
0.8475	Intermediate Similarity	NPC103420
0.8475	Intermediate Similarity	NPC17809
0.8475	Intermediate Similarity	NPC102540
0.8475	Intermediate Similarity	NPC105031
0.8475	Intermediate Similarity	NPC188022
0.8462	Intermediate Similarity	NPC78119
0.8462	Intermediate Similarity	NPC216468
0.8462	Intermediate Similarity	NPC132078
0.8462	Intermediate Similarity	NPC122005
0.8462	Intermediate Similarity	NPC92730
0.8462	Intermediate Similarity	NPC51333
0.8462	Intermediate Similarity	NPC252821
0.8455	Intermediate Similarity	NPC268032
0.8455	Intermediate Similarity	NPC95716
0.8455	Intermediate Similarity	NPC151537
0.8447	Intermediate Similarity	NPC292730
0.8447	Intermediate Similarity	NPC132271
0.8447	Intermediate Similarity	NPC216520
0.8447	Intermediate Similarity	NPC82664
0.8435	Intermediate Similarity	NPC69006
0.8426	Intermediate Similarity	NPC61033
0.8426	Intermediate Similarity	NPC305603
0.8421	Intermediate Similarity	NPC206
0.8421	Intermediate Similarity	NPC190514
0.8411	Intermediate Similarity	NPC154899
0.8411	Intermediate Similarity	NPC233396
0.8407	Intermediate Similarity	NPC150624
0.8407	Intermediate Similarity	NPC141090
0.8403	Intermediate Similarity	NPC276212
0.8403	Intermediate Similarity	NPC267846
0.8403	Intermediate Similarity	NPC62952
0.84	Intermediate Similarity	NPC123273
0.84	Intermediate Similarity	NPC280347
0.84	Intermediate Similarity	NPC242240
0.84	Intermediate Similarity	NPC177420
0.84	Intermediate Similarity	NPC70436
0.84	Intermediate Similarity	NPC318325
0.8393	Intermediate Similarity	NPC249270
0.839	Intermediate Similarity	NPC159132
0.839	Intermediate Similarity	NPC224342
0.8378	Intermediate Similarity	NPC46940
0.8378	Intermediate Similarity	NPC473521
0.8376	Intermediate Similarity	NPC36016
0.8376	Intermediate Similarity	NPC100099
0.8365	Intermediate Similarity	NPC225464
0.8364	Intermediate Similarity	NPC44732
0.8362	Intermediate Similarity	NPC102639
0.835	Intermediate Similarity	NPC144682
0.835	Intermediate Similarity	NPC274678
0.8348	Intermediate Similarity	NPC184302
0.8333	Intermediate Similarity	NPC72158
0.8333	Intermediate Similarity	NPC169250
0.8333	Intermediate Similarity	NPC23126
0.8333	Intermediate Similarity	NPC116513
0.8333	Intermediate Similarity	NPC190043
0.8333	Intermediate Similarity	NPC98254
0.8333	Intermediate Similarity	NPC271440
0.8333	Intermediate Similarity	NPC103356
0.8333	Intermediate Similarity	NPC54765
0.8333	Intermediate Similarity	NPC266689
0.8333	Intermediate Similarity	NPC92623
0.8333	Intermediate Similarity	NPC100067
0.8333	Intermediate Similarity	NPC162612
0.8333	Intermediate Similarity	NPC149796
0.8333	Intermediate Similarity	NPC135464
0.8333	Intermediate Similarity	NPC30501
0.8333	Intermediate Similarity	NPC105157

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 NPC61885 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	280
0.1-0.2	1044
0.2-0.3	1279
0.3-0.4	2963
0.4-0.5	1887
0.5-0.6	1172
0.6-0.7	443
0.7-0.8	68
0.8-0.85	7
0.85-0.9	6
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.94	High Similarity	NPD846	Approved
0.94	High Similarity	NPD940	Approved
0.89	High Similarity	NPD2859	Approved
0.89	High Similarity	NPD2860	Approved
0.88	High Similarity	NPD2934	Approved
0.88	High Similarity	NPD2933	Approved
0.8738	High Similarity	NPD1242	Phase 1
0.8641	High Similarity	NPD3020	Approved
0.8611	High Similarity	NPD4750	Phase 3
0.835	Intermediate Similarity	NPD1809	Phase 2
0.8333	Intermediate Similarity	NPD845	Approved
0.813	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.8103	Intermediate Similarity	NPD1548	Phase 1
0.8077	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD844	Approved
0.7983	Intermediate Similarity	NPD1610	Phase 2
0.7967	Intermediate Similarity	NPD4908	Phase 1
0.7946	Intermediate Similarity	NPD3021	Approved
0.7946	Intermediate Similarity	NPD3022	Approved
0.7903	Intermediate Similarity	NPD4625	Phase 3
0.79	Intermediate Similarity	NPD111	Approved
0.7895	Intermediate Similarity	NPD7635	Approved
0.7797	Intermediate Similarity	NPD5304	Approved
0.7797	Intermediate Similarity	NPD5303	Approved
0.7768	Intermediate Similarity	NPD2342	Discontinued
0.7757	Intermediate Similarity	NPD288	Approved
0.7706	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.7706	Intermediate Similarity	NPD3028	Approved
0.7686	Intermediate Similarity	NPD422	Phase 1
0.7667	Intermediate Similarity	NPD4589	Approved
0.7652	Intermediate Similarity	NPD6124	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD3027	Phase 3
0.76	Intermediate Similarity	NPD9089	Approved
0.7578	Intermediate Similarity	NPD1555	Discontinued
0.7561	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7561	Intermediate Similarity	NPD4749	Approved
0.754	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7521	Intermediate Similarity	NPD2228	Approved
0.7521	Intermediate Similarity	NPD2229	Approved
0.7521	Intermediate Similarity	NPD2234	Approved
0.7521	Intermediate Similarity	NPD7159	Clinical (unspecified phase)
0.7521	Intermediate Similarity	NPD5238	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD9093	Approved
0.75	Intermediate Similarity	NPD6405	Approved
0.75	Intermediate Similarity	NPD6407	Approved
0.746	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7458	Intermediate Similarity	NPD1476	Clinical (unspecified phase)
0.7442	Intermediate Similarity	NPD1240	Approved
0.744	Intermediate Similarity	NPD1131	Approved
0.744	Intermediate Similarity	NPD1133	Approved
0.744	Intermediate Similarity	NPD1129	Approved
0.744	Intermediate Similarity	NPD1135	Approved
0.744	Intermediate Similarity	NPD1134	Approved
0.7422	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7405	Intermediate Similarity	NPD3553	Approved
0.7405	Intermediate Similarity	NPD3555	Approved
0.7405	Intermediate Similarity	NPD3554	Approved
0.7405	Intermediate Similarity	NPD3552	Approved
0.7381	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7364	Intermediate Similarity	NPD9273	Approved
0.7355	Intermediate Similarity	NPD3091	Approved
0.7355	Intermediate Similarity	NPD7330	Discontinued
0.7348	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD7325	Clinical (unspecified phase)
0.7328	Intermediate Similarity	NPD1607	Approved
0.7308	Intermediate Similarity	NPD943	Approved
0.7308	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD1613	Approved
0.7302	Intermediate Similarity	NPD1164	Approved
0.7295	Intermediate Similarity	NPD4093	Discontinued
0.7287	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.728	Intermediate Similarity	NPD4659	Approved
0.7258	Intermediate Similarity	NPD3092	Approved
0.725	Intermediate Similarity	NPD6671	Approved
0.7246	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7236	Intermediate Similarity	NPD4059	Approved
0.7236	Intermediate Similarity	NPD3019	Approved
0.7236	Intermediate Similarity	NPD2286	Discontinued
0.7236	Intermediate Similarity	NPD2932	Approved
0.72	Intermediate Similarity	NPD2561	Approved
0.72	Intermediate Similarity	NPD2562	Approved
0.7197	Intermediate Similarity	NPD2568	Approved
0.7193	Intermediate Similarity	NPD9610	Approved
0.7193	Intermediate Similarity	NPD9608	Approved
0.7188	Intermediate Similarity	NPD3018	Phase 2
0.7188	Intermediate Similarity	NPD2861	Phase 2
0.7179	Intermediate Similarity	NPD1792	Phase 2
0.7179	Intermediate Similarity	NPD5451	Approved
0.7179	Intermediate Similarity	NPD9380	Clinical (unspecified phase)
0.7174	Intermediate Similarity	NPD7390	Discontinued
0.717	Intermediate Similarity	NPD9094	Approved
0.7165	Intermediate Similarity	NPD3094	Phase 2
0.7165	Intermediate Similarity	NPD4103	Phase 2
0.7165	Intermediate Similarity	NPD4104	Clinical (unspecified phase)
0.7165	Intermediate Similarity	NPD4339	Clinical (unspecified phase)
0.7154	Intermediate Similarity	NPD4235	Clinical (unspecified phase)
0.7154	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7122	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7121	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7121	Intermediate Similarity	NPD5124	Phase 1
0.712	Intermediate Similarity	NPD1201	Approved
0.7097	Intermediate Similarity	NPD4626	Approved
0.7094	Intermediate Similarity	NPD2684	Approved
0.709	Intermediate Similarity	NPD1510	Phase 2
0.7069	Intermediate Similarity	NPD1445	Approved
0.7069	Intermediate Similarity	NPD968	Approved
0.7069	Intermediate Similarity	NPD1444	Approved
0.705	Intermediate Similarity	NPD7213	Phase 3
0.705	Intermediate Similarity	NPD7212	Phase 2
0.7045	Intermediate Similarity	NPD4060	Phase 1
0.704	Intermediate Similarity	NPD3143	Discontinued
0.7037	Intermediate Similarity	NPD5408	Approved
0.7037	Intermediate Similarity	NPD5405	Approved
0.7037	Intermediate Similarity	NPD5404	Approved
0.7037	Intermediate Similarity	NPD2935	Discontinued
0.7037	Intermediate Similarity	NPD5406	Approved
0.7031	Intermediate Similarity	NPD2797	Approved
0.7025	Intermediate Similarity	NPD497	Approved
0.7008	Intermediate Similarity	NPD2982	Phase 2
0.7008	Intermediate Similarity	NPD2983	Phase 2
0.7008	Intermediate Similarity	NPD6583	Phase 3
0.7008	Intermediate Similarity	NPD6582	Phase 2
0.7	Intermediate Similarity	NPD5535	Approved
0.7	Intermediate Similarity	NPD7447	Phase 1
0.6992	Remote Similarity	NPD856	Approved
0.6992	Remote Similarity	NPD16	Approved
0.6985	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6985	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6967	Remote Similarity	NPD6387	Discontinued
0.696	Remote Similarity	NPD1751	Approved
0.696	Remote Similarity	NPD3095	Discontinued
0.6957	Remote Similarity	NPD3750	Approved
0.6957	Remote Similarity	NPD5700	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD9500	Approved
0.6942	Remote Similarity	NPD5283	Phase 1
0.6942	Remote Similarity	NPD495	Approved
0.6942	Remote Similarity	NPD496	Approved
0.6942	Remote Similarity	NPD498	Approved
0.694	Remote Similarity	NPD4097	Suspended
0.6935	Remote Similarity	NPD2226	Clinical (unspecified phase)
0.6934	Remote Similarity	NPD1549	Phase 2
0.6929	Remote Similarity	NPD3070	Discontinued
0.6929	Remote Similarity	NPD2981	Phase 2
0.6917	Remote Similarity	NPD228	Approved
0.6912	Remote Similarity	NPD6100	Approved
0.6912	Remote Similarity	NPD6099	Approved
0.6911	Remote Similarity	NPD7636	Approved
0.6905	Remote Similarity	NPD2688	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD3847	Discontinued
0.6905	Remote Similarity	NPD3421	Phase 3
0.6899	Remote Similarity	NPD1470	Approved
0.6875	Remote Similarity	NPD4380	Phase 2
0.6864	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.6864	Remote Similarity	NPD290	Approved
0.686	Remote Similarity	NPD7843	Approved
0.6855	Remote Similarity	NPD318	Approved
0.6855	Remote Similarity	NPD317	Approved
0.6849	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6846	Remote Similarity	NPD3691	Phase 2
0.6846	Remote Similarity	NPD6584	Phase 3
0.6846	Remote Similarity	NPD3690	Phase 2
0.6835	Remote Similarity	NPD3400	Discontinued
0.6829	Remote Similarity	NPD255	Approved
0.6829	Remote Similarity	NPD256	Approved
0.6828	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6828	Remote Similarity	NPD7411	Suspended
0.6825	Remote Similarity	NPD2667	Approved
0.6825	Remote Similarity	NPD2668	Approved
0.6822	Remote Similarity	NPD6696	Suspended
0.6822	Remote Similarity	NPD8651	Approved
0.6807	Remote Similarity	NPD74	Approved
0.6807	Remote Similarity	NPD9266	Approved
0.6803	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.68	Remote Similarity	NPD9087	Approved
0.68	Remote Similarity	NPD1759	Phase 1
0.6794	Remote Similarity	NPD4208	Discontinued
0.6794	Remote Similarity	NPD5736	Approved
0.6791	Remote Similarity	NPD468	Phase 1
0.6791	Remote Similarity	NPD2238	Phase 2
0.6788	Remote Similarity	NPD2796	Approved
0.6774	Remote Similarity	NPD9493	Approved
0.6769	Remote Similarity	NPD3055	Approved
0.6769	Remote Similarity	NPD3053	Approved
0.6767	Remote Similarity	NPD3268	Approved
0.6765	Remote Similarity	NPD4978	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD4538	Approved
0.6765	Remote Similarity	NPD4536	Approved
0.6765	Remote Similarity	NPD4537	Clinical (unspecified phase)
0.6763	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6763	Remote Similarity	NPD5698	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD7768	Phase 2
0.6746	Remote Similarity	NPD1651	Approved
0.6746	Remote Similarity	NPD5691	Approved
0.6744	Remote Similarity	NPD1669	Approved
0.6723	Remote Similarity	NPD9267	Approved
0.6723	Remote Similarity	NPD9264	Approved
0.6723	Remote Similarity	NPD9263	Approved
0.6721	Remote Similarity	NPD9379	Approved
0.6721	Remote Similarity	NPD821	Approved
0.6721	Remote Similarity	NPD9377	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