NPASS Compound

Structure

NPC53146 OpenBabel07101719242D 26 28 0 0 1 0 0 0 0 0999 V2000 -2.1623 -4.0132 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3497 0.0723 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 1.0151 -2.4888 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4942 -0.5391 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3349 -3.2219 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4914 -0.4644 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 -2.1565 -2.6863 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 -0.9309 -1.3653 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2256 -2.3209 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6623 -3.1472 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.0225 -2.1863 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 -3.1716 -1.1974 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 0.8660 0.5000 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 -1.1623 -4.0132 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -3.8488 -2.7496 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 -4.1271 -0.9027 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 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 21 1 0 0 0 0 2 24 1 0 0 0 0 3 25 1 0 0 0 0 4 26 1 0 0 0 0 5 7 1 0 0 0 0 5 11 1 0 0 0 0 6 8 1 0 0 0 0 6 12 2 0 0 0 0 7 14 1 0 0 0 0 8 17 2 0 0 0 0 9 11 2 0 0 0 0 9 16 1 0 0 0 0 10 13 2 0 0 0 0 10 15 1 0 0 0 0 11 18 1 0 0 0 0 12 13 1 0 0 0 0 12 18 1 0 0 0 0 13 14 1 0 0 0 0 14 21 1 6 0 0 0 15 17 1 0 0 0 0 15 22 2 0 0 0 0 16 19 2 0 0 0 0 16 23 1 0 0 0 0 17 24 1 0 0 0 0 18 20 2 0 0 0 0 19 20 1 0 0 0 0 19 25 1 0 0 0 0 20 26 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	357.16
Volume:	365.299
LogP:	2.598
LogD:	1.904
LogS:	-3.345
# Rotatable Bonds:	3
TPSA:	77.35
# H-Bond Aceptor:	6
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.852
Synthetic Accessibility Score:	3.722
Fsp3:	0.4
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.765
MDCK Permeability:	1.8399328837404028e-05
Pgp-inhibitor:	0.005
Pgp-substrate:	0.04
Human Intestinal Absorption (HIA):	0.021
20% Bioavailability (F20%):	0.056
30% Bioavailability (F30%):	0.008

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.934
Plasma Protein Binding (PPB):	89.47469329833984%
Volume Distribution (VD):	1.163
Pgp-substrate:	9.990425109863281%

ADMET: Metabolism

CYP1A2-inhibitor:	0.857
CYP1A2-substrate:	0.977
CYP2C19-inhibitor:	0.038
CYP2C19-substrate:	0.848
CYP2C9-inhibitor:	0.037
CYP2C9-substrate:	0.717
CYP2D6-inhibitor:	0.39
CYP2D6-substrate:	0.782
CYP3A4-inhibitor:	0.106
CYP3A4-substrate:	0.888

ADMET: Excretion

Clearance (CL):	8.574
Half-life (T1/2):	0.696

ADMET: Toxicity

hERG Blockers:	0.082
Human Hepatotoxicity (H-HT):	0.711
Drug-inuced Liver Injury (DILI):	0.439
AMES Toxicity:	0.172
Rat Oral Acute Toxicity:	0.551
Maximum Recommended Daily Dose:	0.473
Skin Sensitization:	0.52
Carcinogencity:	0.077
Eye Corrosion:	0.003
Eye Irritation:	0.019
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: NPC53146

Natural Product ID:	NPC53146
*Common Name:**	(-)-3-Demethyldemecolcine
IUPAC Name:	(7S)-3-hydroxy-1,2,10-trimethoxy-7-(methylamino)-6,7-dihydro-5H-benzo[a]heptalen-9-one
Synonyms:
Standard InCHIKey:	XUCTUYPXJOLWKI-AWEZNQCLSA-N
Standard InCHI:	InChI=1S/C20H23NO5/c1-21-14-7-5-11-9-16(23)19(25-3)20(26-4)18(11)12-6-8-17(24-2)15(22)10-13(12)14/h6,8-10,14,21,23H,5,7H2,1-4H3/t14-/m0/s1
SMILES:	CN[C@H]1CCc2cc(c(c(c2-c2ccc(c(=O)cc12)OC)OC)OC)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL498123
PubChem CID:	14413737
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004150] Hydrocarbon derivatives [CHEMONTID:0001650] Tropones

*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
NPO24146	Colchicum brachyphyllum	Species	Colchicaceae	Eukaryota	n.a.	Jordanian	n.a.	PMID[15730238]
NPO24146	Colchicum brachyphyllum	Species	Colchicaceae	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
EC50	3
MIC	4
Others	1

Activity Type	# Activity
Cell Line	3
Organism	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT83	Cell Line	MCF7	Homo sapiens	EC50	=	790.0	nM	PMID[447427]
NPT397	Cell Line	NCI-H460	Homo sapiens	EC50	=	1100.0	nM	PMID[447427]
NPT395	Cell Line	SF-268	Homo sapiens	EC50	=	3200.0	nM	PMID[447427]
NPT140	Organism	Artemia	Artemia	LC50	=	71.5	ug.mL-1	PMID[447427]
NPT729	Organism	Micrococcus luteus	Micrococcus luteus	MIC	>	500.0	ug.mL-1	PMID[447427]
NPT602	Organism	Mycobacterium smegmatis	Mycobacterium smegmatis	MIC	>	500.0	ug.mL-1	PMID[447427]
NPT312	Organism	Saccharomyces cerevisiae	Saccharomyces cerevisiae	MIC	>	500.0	ug.mL-1	PMID[447427]
NPT21	Organism	Aspergillus niger	Aspergillus niger	MIC	>	500.0	ug.mL-1	PMID[447427]

☑ 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 NPC53146 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	274
0.1-0.2	1635
0.2-0.3	6936
0.3-0.4	11037
0.4-0.5	4597
0.5-0.6	8170
0.6-0.7	8993
0.7-0.8	1039
0.8-0.85	4
0.85-0.9	5
0.9-0.95	3
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC188120
1.0	High Similarity	NPC286790
0.9542	High Similarity	NPC190931
0.9236	High Similarity	NPC202839
0.9236	High Similarity	NPC66678
0.9156	High Similarity	NPC218575
0.8917	High Similarity	NPC14005
0.8917	High Similarity	NPC226941
0.8917	High Similarity	NPC108957
0.8917	High Similarity	NPC44642
0.8537	High Similarity	NPC189782
0.8214	Intermediate Similarity	NPC3906
0.8047	Intermediate Similarity	NPC3375
0.8047	Intermediate Similarity	NPC255607
0.8024	Intermediate Similarity	NPC329837
0.8	Intermediate Similarity	NPC474507
0.7976	Intermediate Similarity	NPC226428
0.7941	Intermediate Similarity	NPC24465
0.7907	Intermediate Similarity	NPC83198
0.7907	Intermediate Similarity	NPC204908
0.7895	Intermediate Similarity	NPC13916
0.7895	Intermediate Similarity	NPC264850
0.7892	Intermediate Similarity	NPC475557
0.7886	Intermediate Similarity	NPC476577
0.7886	Intermediate Similarity	NPC173416
0.7886	Intermediate Similarity	NPC148709
0.7857	Intermediate Similarity	NPC262641
0.7812	Intermediate Similarity	NPC144284
0.7784	Intermediate Similarity	NPC477564
0.7784	Intermediate Similarity	NPC2295
0.7778	Intermediate Similarity	NPC294249
0.7771	Intermediate Similarity	NPC152680
0.7771	Intermediate Similarity	NPC190783
0.7771	Intermediate Similarity	NPC277669
0.7771	Intermediate Similarity	NPC76213
0.7771	Intermediate Similarity	NPC232386
0.7759	Intermediate Similarity	NPC26240
0.7759	Intermediate Similarity	NPC477562
0.7759	Intermediate Similarity	NPC69712
0.7735	Intermediate Similarity	NPC186546
0.7735	Intermediate Similarity	NPC476576
0.7727	Intermediate Similarity	NPC329969
0.7727	Intermediate Similarity	NPC291847
0.7725	Intermediate Similarity	NPC114124
0.7714	Intermediate Similarity	NPC239775
0.7692	Intermediate Similarity	NPC175890
0.7692	Intermediate Similarity	NPC82457
0.7692	Intermediate Similarity	NPC48490
0.7692	Intermediate Similarity	NPC274661
0.7692	Intermediate Similarity	NPC11296
0.767	Intermediate Similarity	NPC192135
0.767	Intermediate Similarity	NPC66341
0.767	Intermediate Similarity	NPC477020
0.7658	Intermediate Similarity	NPC32778
0.7651	Intermediate Similarity	NPC207824
0.7651	Intermediate Similarity	NPC60538
0.765	Intermediate Similarity	NPC60295
0.765	Intermediate Similarity	NPC191132
0.7644	Intermediate Similarity	NPC204947
0.7588	Intermediate Similarity	NPC160931
0.7588	Intermediate Similarity	NPC37205
0.7586	Intermediate Similarity	NPC193853
0.7586	Intermediate Similarity	NPC56887
0.7586	Intermediate Similarity	NPC223077
0.7582	Intermediate Similarity	NPC57036
0.758	Intermediate Similarity	NPC126836
0.756	Intermediate Similarity	NPC85747
0.756	Intermediate Similarity	NPC8337
0.7557	Intermediate Similarity	NPC168753
0.7557	Intermediate Similarity	NPC118274
0.7532	Intermediate Similarity	NPC105513
0.7529	Intermediate Similarity	NPC209377
0.75	Intermediate Similarity	NPC470324
0.75	Intermediate Similarity	NPC32154
0.7487	Intermediate Similarity	NPC281629
0.7486	Intermediate Similarity	NPC81247
0.7486	Intermediate Similarity	NPC476573
0.7486	Intermediate Similarity	NPC35627
0.7485	Intermediate Similarity	NPC476571
0.7485	Intermediate Similarity	NPC147390
0.7485	Intermediate Similarity	NPC135538
0.7485	Intermediate Similarity	NPC428
0.7485	Intermediate Similarity	NPC246587
0.7485	Intermediate Similarity	NPC24233
0.7471	Intermediate Similarity	NPC124433
0.7471	Intermediate Similarity	NPC293871
0.747	Intermediate Similarity	NPC476843
0.747	Intermediate Similarity	NPC476841
0.747	Intermediate Similarity	NPC473934
0.7468	Intermediate Similarity	NPC238810
0.7459	Intermediate Similarity	NPC476574
0.7459	Intermediate Similarity	NPC286119
0.7459	Intermediate Similarity	NPC312918
0.7459	Intermediate Similarity	NPC155442
0.7459	Intermediate Similarity	NPC477561
0.7459	Intermediate Similarity	NPC298339
0.7458	Intermediate Similarity	NPC109925
0.7456	Intermediate Similarity	NPC476579
0.744	Intermediate Similarity	NPC103379
0.744	Intermediate Similarity	NPC477565
0.7429	Intermediate Similarity	NPC253043
0.7429	Intermediate Similarity	NPC136508
0.7429	Intermediate Similarity	NPC2770
0.7429	Intermediate Similarity	NPC477563
0.7429	Intermediate Similarity	NPC121275
0.7429	Intermediate Similarity	NPC78222
0.7429	Intermediate Similarity	NPC212794
0.7429	Intermediate Similarity	NPC284183
0.7429	Intermediate Similarity	NPC39103
0.7429	Intermediate Similarity	NPC4138
0.7429	Intermediate Similarity	NPC13504
0.7429	Intermediate Similarity	NPC196447
0.7429	Intermediate Similarity	NPC306843
0.7429	Intermediate Similarity	NPC96603
0.7427	Intermediate Similarity	NPC204828
0.7427	Intermediate Similarity	NPC184026
0.7427	Intermediate Similarity	NPC278799
0.7427	Intermediate Similarity	NPC207757
0.7427	Intermediate Similarity	NPC193949
0.7427	Intermediate Similarity	NPC127674
0.7427	Intermediate Similarity	NPC39701
0.7427	Intermediate Similarity	NPC110416
0.7427	Intermediate Similarity	NPC189266
0.7427	Intermediate Similarity	NPC172765
0.7427	Intermediate Similarity	NPC249797
0.7427	Intermediate Similarity	NPC469817
0.7427	Intermediate Similarity	NPC5238
0.7427	Intermediate Similarity	NPC2413
0.7427	Intermediate Similarity	NPC295691
0.7427	Intermediate Similarity	NPC276588
0.7427	Intermediate Similarity	NPC54379
0.7425	Intermediate Similarity	NPC191376
0.7425	Intermediate Similarity	NPC321505
0.7425	Intermediate Similarity	NPC179825
0.7418	Intermediate Similarity	NPC290582
0.7418	Intermediate Similarity	NPC185639
0.7418	Intermediate Similarity	NPC251735
0.7418	Intermediate Similarity	NPC7715
0.7418	Intermediate Similarity	NPC181796
0.7418	Intermediate Similarity	NPC311973
0.7418	Intermediate Similarity	NPC42663
0.7418	Intermediate Similarity	NPC30779
0.7418	Intermediate Similarity	NPC239824
0.7418	Intermediate Similarity	NPC271013
0.7418	Intermediate Similarity	NPC104196
0.7418	Intermediate Similarity	NPC290005
0.7418	Intermediate Similarity	NPC90998
0.7418	Intermediate Similarity	NPC258657
0.7418	Intermediate Similarity	NPC182052
0.7418	Intermediate Similarity	NPC8836
0.7418	Intermediate Similarity	NPC222661
0.7418	Intermediate Similarity	NPC49075
0.7418	Intermediate Similarity	NPC223690
0.7418	Intermediate Similarity	NPC229373
0.7418	Intermediate Similarity	NPC54654
0.7418	Intermediate Similarity	NPC279228
0.7418	Intermediate Similarity	NPC15414
0.7418	Intermediate Similarity	NPC285931
0.7418	Intermediate Similarity	NPC328155
0.7418	Intermediate Similarity	NPC217748
0.7414	Intermediate Similarity	NPC247251
0.741	Intermediate Similarity	NPC16353
0.7407	Intermediate Similarity	NPC253429
0.7396	Intermediate Similarity	NPC97221
0.7396	Intermediate Similarity	NPC192768
0.7396	Intermediate Similarity	NPC88249
0.7396	Intermediate Similarity	NPC151895
0.7396	Intermediate Similarity	NPC220858
0.7391	Intermediate Similarity	NPC206737
0.7391	Intermediate Similarity	NPC125649
0.7391	Intermediate Similarity	NPC276026
0.7391	Intermediate Similarity	NPC56764
0.7391	Intermediate Similarity	NPC469659
0.7391	Intermediate Similarity	NPC289258
0.7391	Intermediate Similarity	NPC188378
0.7391	Intermediate Similarity	NPC555
0.7391	Intermediate Similarity	NPC209199
0.7391	Intermediate Similarity	NPC7515
0.7389	Intermediate Similarity	NPC82679
0.7389	Intermediate Similarity	NPC293054
0.7389	Intermediate Similarity	NPC282000
0.7389	Intermediate Similarity	NPC159968
0.7389	Intermediate Similarity	NPC124452
0.7389	Intermediate Similarity	NPC74817
0.7389	Intermediate Similarity	NPC241704
0.7389	Intermediate Similarity	NPC246620
0.7389	Intermediate Similarity	NPC169474
0.7389	Intermediate Similarity	NPC324112
0.7389	Intermediate Similarity	NPC236791
0.7381	Intermediate Similarity	NPC178129
0.738	Intermediate Similarity	NPC256124
0.7377	Intermediate Similarity	NPC135772
0.7377	Intermediate Similarity	NPC167116
0.7377	Intermediate Similarity	NPC254441
0.7377	Intermediate Similarity	NPC274716
0.7371	Intermediate Similarity	NPC324144
0.7368	Intermediate Similarity	NPC471031
0.7368	Intermediate Similarity	NPC469689
0.7366	Intermediate Similarity	NPC196231
0.7365	Intermediate Similarity	NPC474982

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 NPC53146 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	192
0.1-0.2	736
0.2-0.3	1217
0.3-0.4	2213
0.4-0.5	2636
0.5-0.6	1460
0.6-0.7	638
0.7-0.8	55
0.8-0.85	0
0.85-0.9	2
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9542	High Similarity	NPD4585	Approved
0.8917	High Similarity	NPD5090	Approved
0.8917	High Similarity	NPD5089	Approved
0.768	Intermediate Similarity	NPD6843	Phase 3
0.768	Intermediate Similarity	NPD6842	Approved
0.768	Intermediate Similarity	NPD6841	Approved
0.75	Intermediate Similarity	NPD2898	Approved
0.7471	Intermediate Similarity	NPD4666	Phase 3
0.7459	Intermediate Similarity	NPD3534	Clinical (unspecified phase)
0.7457	Intermediate Similarity	NPD4055	Discovery
0.7439	Intermediate Similarity	NPD3060	Approved
0.7418	Intermediate Similarity	NPD8053	Approved
0.7418	Intermediate Similarity	NPD8054	Approved
0.7414	Intermediate Similarity	NPD5709	Phase 3
0.7384	Intermediate Similarity	NPD2978	Approved
0.7384	Intermediate Similarity	NPD2977	Approved
0.7381	Intermediate Similarity	NPD3647	Clinical (unspecified phase)
0.7353	Intermediate Similarity	NPD4005	Discontinued
0.7321	Intermediate Similarity	NPD1424	Approved
0.7294	Intermediate Similarity	NPD3687	Approved
0.7294	Intermediate Similarity	NPD3686	Approved
0.7188	Intermediate Similarity	NPD2669	Clinical (unspecified phase)
0.7182	Intermediate Similarity	NPD6042	Phase 2
0.7182	Intermediate Similarity	NPD42	Phase 2
0.7143	Intermediate Similarity	NPD2563	Approved
0.7143	Intermediate Similarity	NPD2677	Approved
0.7143	Intermediate Similarity	NPD2560	Approved
0.7134	Intermediate Similarity	NPD6111	Discontinued
0.712	Intermediate Similarity	NPD8453	Clinical (unspecified phase)
0.7118	Intermediate Similarity	NPD3158	Phase 1
0.7118	Intermediate Similarity	NPD3536	Discontinued
0.7118	Intermediate Similarity	NPD3157	Approved
0.7108	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD7124	Phase 2
0.7099	Intermediate Similarity	NPD1132	Approved
0.7099	Intermediate Similarity	NPD1130	Approved
0.7099	Intermediate Similarity	NPD554	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD1136	Approved
0.7081	Intermediate Similarity	NPD3027	Phase 3
0.7073	Intermediate Similarity	NPD2653	Approved
0.7066	Intermediate Similarity	NPD4664	Clinical (unspecified phase)
0.7062	Intermediate Similarity	NPD3450	Approved
0.7062	Intermediate Similarity	NPD3452	Approved
0.7062	Intermediate Similarity	NPD2493	Approved
0.7062	Intermediate Similarity	NPD2494	Approved
0.7044	Intermediate Similarity	NPD3055	Approved
0.7044	Intermediate Similarity	NPD3053	Approved
0.7043	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD5241	Discontinued
0.7037	Intermediate Similarity	NPD597	Approved
0.7037	Intermediate Similarity	NPD598	Approved
0.7037	Intermediate Similarity	NPD601	Approved
0.7037	Intermediate Similarity	NPD2488	Approved
0.7037	Intermediate Similarity	NPD2028	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD2490	Approved
0.7033	Intermediate Similarity	NPD8099	Discontinued
0.7033	Intermediate Similarity	NPD2163	Approved
0.7033	Intermediate Similarity	NPD8251	Approved
0.7033	Intermediate Similarity	NPD8252	Approved
0.7029	Intermediate Similarity	NPD7298	Approved
0.7024	Intermediate Similarity	NPD4162	Approved
0.7021	Intermediate Similarity	NPD7906	Approved
0.7018	Intermediate Similarity	NPD1754	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD4584	Approved
0.7017	Intermediate Similarity	NPD27	Approved
0.7017	Intermediate Similarity	NPD2489	Approved
0.7006	Intermediate Similarity	NPD3882	Suspended
0.6995	Remote Similarity	NPD8156	Discontinued
0.6994	Remote Similarity	NPD2674	Phase 3
0.6977	Remote Similarity	NPD7526	Approved
0.6977	Remote Similarity	NPD7527	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD52	Approved
0.697	Remote Similarity	NPD817	Approved
0.697	Remote Similarity	NPD2568	Approved
0.697	Remote Similarity	NPD823	Approved
0.6966	Remote Similarity	NPD7975	Clinical (unspecified phase)
0.6961	Remote Similarity	NPD2970	Approved
0.6961	Remote Similarity	NPD2969	Approved
0.6959	Remote Similarity	NPD7237	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD5297	Approved
0.6959	Remote Similarity	NPD4357	Discontinued
0.6954	Remote Similarity	NPD4583	Approved
0.6954	Remote Similarity	NPD4582	Approved
0.6951	Remote Similarity	NPD2238	Phase 2
0.6941	Remote Similarity	NPD2219	Phase 1
0.6936	Remote Similarity	NPD6030	Approved
0.6936	Remote Similarity	NPD6031	Approved
0.6936	Remote Similarity	NPD3640	Phase 3
0.6936	Remote Similarity	NPD3641	Approved
0.6936	Remote Similarity	NPD3639	Approved
0.6935	Remote Similarity	NPD3936	Clinical (unspecified phase)
0.6935	Remote Similarity	NPD7549	Discontinued
0.691	Remote Similarity	NPD4581	Clinical (unspecified phase)
0.691	Remote Similarity	NPD6788	Approved
0.6906	Remote Similarity	NPD3051	Approved
0.6906	Remote Similarity	NPD6071	Discontinued
0.6906	Remote Similarity	NPD4010	Discontinued
0.6904	Remote Similarity	NPD4004	Approved
0.6904	Remote Similarity	NPD4002	Approved
0.6898	Remote Similarity	NPD7313	Approved
0.6898	Remote Similarity	NPD4578	Approved
0.6898	Remote Similarity	NPD7312	Approved
0.6898	Remote Similarity	NPD7311	Approved
0.6898	Remote Similarity	NPD7310	Approved
0.6898	Remote Similarity	NPD4577	Approved
0.6894	Remote Similarity	NPD602	Approved
0.6894	Remote Similarity	NPD9619	Approved
0.6894	Remote Similarity	NPD9620	Approved
0.6894	Remote Similarity	NPD9621	Approved
0.6894	Remote Similarity	NPD599	Approved
0.6882	Remote Similarity	NPD7039	Approved
0.6882	Remote Similarity	NPD7038	Approved
0.6881	Remote Similarity	NPD7827	Phase 1
0.6879	Remote Similarity	NPD1350	Approved
0.6879	Remote Similarity	NPD5261	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD1349	Approved
0.6879	Remote Similarity	NPD1351	Approved
0.6878	Remote Similarity	NPD4663	Approved
0.6862	Remote Similarity	NPD7309	Approved
0.686	Remote Similarity	NPD1774	Approved
0.6857	Remote Similarity	NPD3455	Phase 2
0.6856	Remote Similarity	NPD2975	Approved
0.6856	Remote Similarity	NPD2973	Approved
0.6856	Remote Similarity	NPD2974	Approved
0.6852	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6851	Remote Similarity	NPD6107	Approved
0.6848	Remote Similarity	NPD3062	Approved
0.6848	Remote Similarity	NPD3061	Approved
0.6848	Remote Similarity	NPD3059	Approved
0.6845	Remote Similarity	NPD1632	Clinical (unspecified phase)
0.6837	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD3144	Approved
0.6829	Remote Similarity	NPD3145	Approved
0.6828	Remote Similarity	NPD6297	Approved
0.6824	Remote Similarity	NPD4236	Phase 3
0.6824	Remote Similarity	NPD4237	Approved
0.6821	Remote Similarity	NPD4160	Clinical (unspecified phase)
0.6821	Remote Similarity	NPD1771	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD4675	Approved
0.6818	Remote Similarity	NPD4678	Approved
0.6813	Remote Similarity	NPD9622	Approved
0.6813	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6811	Remote Similarity	NPD3933	Discontinued
0.6811	Remote Similarity	NPD5096	Phase 3
0.6811	Remote Similarity	NPD5095	Phase 3
0.681	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.681	Remote Similarity	NPD600	Approved
0.681	Remote Similarity	NPD596	Approved
0.6802	Remote Similarity	NPD3845	Phase 1
0.6802	Remote Similarity	NPD2422	Clinical (unspecified phase)
0.6793	Remote Similarity	NPD3489	Phase 3
0.679	Remote Similarity	NPD859	Approved
0.679	Remote Similarity	NPD858	Approved
0.6789	Remote Similarity	NPD3857	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD2156	Approved
0.6786	Remote Similarity	NPD2154	Approved
0.6786	Remote Similarity	NPD2155	Approved
0.6784	Remote Similarity	NPD4040	Phase 1
0.6782	Remote Similarity	NPD2676	Approved
0.6782	Remote Similarity	NPD2675	Approved
0.678	Remote Similarity	NPD4773	Phase 2
0.678	Remote Similarity	NPD4772	Phase 2
0.678	Remote Similarity	NPD6072	Discontinued
0.6779	Remote Similarity	NPD7907	Approved
0.6776	Remote Similarity	NPD5242	Approved
0.677	Remote Similarity	NPD5310	Approved
0.677	Remote Similarity	NPD5311	Approved
0.677	Remote Similarity	NPD9634	Clinical (unspecified phase)
0.6768	Remote Similarity	NPD3179	Approved
0.6768	Remote Similarity	NPD3180	Approved
0.6768	Remote Similarity	NPD3057	Approved
0.6766	Remote Similarity	NPD5314	Approved
0.6765	Remote Similarity	NPD1372	Clinical (unspecified phase)
0.6761	Remote Similarity	NPD2651	Approved
0.6761	Remote Similarity	NPD824	Approved
0.6761	Remote Similarity	NPD2649	Approved
0.6761	Remote Similarity	NPD7261	Clinical (unspecified phase)
0.6751	Remote Similarity	NPD4580	Approved
0.6747	Remote Similarity	NPD1613	Approved
0.6747	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6742	Remote Similarity	NPD1934	Approved
0.6739	Remote Similarity	NPD4481	Phase 3
0.6736	Remote Similarity	NPD7296	Approved
0.6724	Remote Similarity	NPD3645	Discontinued
0.6721	Remote Similarity	NPD4166	Phase 2
0.672	Remote Similarity	NPD2971	Approved
0.672	Remote Similarity	NPD2968	Approved
0.6705	Remote Similarity	NPD6666	Approved
0.6705	Remote Similarity	NPD3122	Phase 3
0.6705	Remote Similarity	NPD6667	Approved
0.6704	Remote Similarity	NPD2801	Approved
0.6704	Remote Similarity	NPD6818	Clinical (unspecified phase)
0.6687	Remote Similarity	NPD259	Phase 1
0.6686	Remote Similarity	NPD6029	Clinical (unspecified phase)
0.6686	Remote Similarity	NPD651	Clinical (unspecified phase)
0.6686	Remote Similarity	NPD6028	Clinical (unspecified phase)
0.6684	Remote Similarity	NPD6853	Approved
0.6684	Remote Similarity	NPD6851	Approved
0.6683	Remote Similarity	NPD3533	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