NPASS Compound

Structure

CID125828 OpenBabel06191715482D 30 33 0 0 1 0 0 0 0 0999 V2000 -3.2396 -0.7783 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5539 1.7913 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5539 1.7913 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7419 -1.8102 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8507 0.5257 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9711 -2.7602 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2547 -2.5277 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6519 0.4253 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7859 1.9253 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0539 -1.0747 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4060 1.0488 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4311 0.8262 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9199 -0.5747 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8678 -1.8019 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5531 0.4537 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1294 -1.7272 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6117 0.7911 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4060 -1.1982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3143 -1.1575 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.1878 -0.5747 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4311 -0.9757 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5232 -0.5458 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.1878 0.4253 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.9972 -0.0747 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.9199 0.4253 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.0539 0.9253 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5633 -0.8262 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.1800 -2.1485 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 5.7859 0.9253 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 2 26 1 0 0 0 0 3 26 1 0 0 0 0 4 27 1 0 0 0 0 6 29 1 0 0 0 0 7 29 1 0 0 0 0 8 30 1 0 0 0 0 9 30 1 0 0 0 0 10 13 1 0 0 0 0 10 20 1 0 0 0 0 11 12 1 0 0 0 0 12 24 1 0 0 0 0 13 25 1 0 0 0 0 14 16 1 0 0 0 0 14 21 2 0 0 0 0 15 17 1 0 0 0 0 15 22 1 0 0 0 0 16 27 1 0 0 0 0 17 28 1 0 0 0 0 18 20 2 0 0 0 0 18 21 1 0 0 0 0 19 1 1 1 0 0 0 19 22 1 0 0 0 0 19 29 1 0 0 0 0 20 23 1 0 0 0 0 21 24 1 0 0 0 0 22 27 1 1 0 0 0 23 11 1 1 0 0 0 23 26 1 0 0 0 0 24 28 1 6 0 0 0 25 26 1 0 0 0 0 25 30 1 1 0 0 0 27 28 1 1 0 0 0 28 5 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	412.38
Volume:	475.339
LogP:	5.986
LogD:	4.46
LogS:	-5.057
# Rotatable Bonds:	3
TPSA:	6.48
# H-Bond Aceptor:	2
# H-Bond Donor:	0
# Rings:	4
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.53
Synthetic Accessibility Score:	5.018
Fsp3:	0.857
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:	-5.051
MDCK Permeability:	1.1234069461352192e-05
Pgp-inhibitor:	1.0
Pgp-substrate:	0.077
Human Intestinal Absorption (HIA):	0.01
20% Bioavailability (F20%):	0.599
30% Bioavailability (F30%):	0.496

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.117
Plasma Protein Binding (PPB):	73.06326293945312%
Volume Distribution (VD):	3.478
Pgp-substrate:	32.00505828857422%

ADMET: Metabolism

CYP1A2-inhibitor:	0.02
CYP1A2-substrate:	0.146
CYP2C19-inhibitor:	0.047
CYP2C19-substrate:	0.992
CYP2C9-inhibitor:	0.061
CYP2C9-substrate:	0.1
CYP2D6-inhibitor:	0.865
CYP2D6-substrate:	0.926
CYP3A4-inhibitor:	0.439
CYP3A4-substrate:	0.927

ADMET: Excretion

Clearance (CL):	12.238
Half-life (T1/2):	0.135

ADMET: Toxicity

hERG Blockers:	0.034
Human Hepatotoxicity (H-HT):	0.6
Drug-inuced Liver Injury (DILI):	0.017
AMES Toxicity:	0.001
Rat Oral Acute Toxicity:	0.488
Maximum Recommended Daily Dose:	0.927
Skin Sensitization:	0.945
Carcinogencity:	0.254
Eye Corrosion:	0.914
Eye Irritation:	0.051
Respiratory Toxicity:	0.972

Download Data

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

Natural Product: NPC125828

Natural Product ID:	NPC125828
*Common Name:**	Buxamine A
IUPAC Name:	n.a.
Synonyms:	Buxamine A
Standard InCHIKey:	ZUILVKYUNYJWMV-JTRBZCFYSA-N
Standard InCHI:	InChI=1S/C28H48N2/c1-19(29(6)7)22-15-17-28(5)24-12-11-23-20(18-21(24)14-16-27(22,28)4)10-13-25(30(8)9)26(23,2)3/h14,18-19,22-25H,10-13,15-17H2,1-9H3/t19-,22+,23+,24+,25-,27+,28-/m0/s1
SMILES:	C[C@@H]([C@H]1CC[C@@]2(C)[C@@H]3CC[C@@H]4C(=CC3=CC[C@]12C)CC[C@@H](C4(C)C)N(C)C)N(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1651047
PubChem CID:	5468622
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0002724] Steroidal alkaloids [CHEMONTID:0002726] Buxus alkaloids

*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
NPO27255	Macaranga alnifolia	Species	Euphorbiaceae	Eukaryota	n.a.	leaf	n.a.	DOI[10.1016/0031-9422(92)80315-6]
NPO27255	Macaranga alnifolia	Species	Euphorbiaceae	Eukaryota	n.a.	Madagascar rainforest	n.a.	PMID[17326683]
NPO27255	Macaranga alnifolia	Species	Euphorbiaceae	Eukaryota	n.a.	fruit	n.a.	PMID[17326683]
NPO26132	Buxus natalensis	Species	Buxaceae	Eukaryota	n.a.	uMhalanga Rocks nature reserve, Durban, South Africa	2007-FEB	PMID[20954721]
NPO11067	Buxus papillosa	Species	Buxaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20954721]
NPO26132	Buxus natalensis	Species	Buxaceae	Eukaryota	n.a.	bark	n.a.	PMID[20954721]
NPO27700	Alphitonia excelsa	Species	Rhamnaceae	Eukaryota	n.a.	xylem	n.a.	PMID[21992235]
NPO4617	Tanacetum cinerariifolium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24253739]
NPO27999	Aconitum nagarum	Species	Ranunculaceae	Eukaryota	n.a.	root	n.a.	Europe PMC[335013]
NPO11067	Buxus papillosa	Species	Buxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5507	Eubotryoides grayana	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11067	Buxus papillosa	Species	Buxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4617	Tanacetum cinerariifolium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5507	Eubotryoides grayana	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27615	Ambrosia deltoidea	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26132	Buxus natalensis	Species	Buxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27999	Aconitum nagarum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27765	Bryopsis plumosa	Species	Bryopsidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11067	Buxus papillosa	Species	Buxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4617	Tanacetum cinerariifolium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27255	Macaranga alnifolia	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27700	Alphitonia excelsa	Species	Rhamnaceae	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
GI50	54
IC50	1

Activity Type	# Activity
Cell Line	54
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT204	Individual Protein	Acetylcholinesterase	Homo sapiens	IC50	=	80000.0	nM	PMID[508101]
NPT367	Cell Line	MDA-N	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[508102]
NPT370	Cell Line	NCI-H23	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[508102]
NPT368	Cell Line	SN12C	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[508102]
NPT369	Cell Line	ACHN	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[508102]
NPT372	Cell Line	HOP-92	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[508102]
NPT116	Cell Line	HL-60	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[508102]
NPT90	Cell Line	DU-145	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[508102]
NPT374	Cell Line	SF-539	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[508102]
NPT375	Cell Line	Malme-3M	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[508102]
NPT373	Cell Line	SK-MEL-5	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[508102]
NPT111	Cell Line	K562	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[508102]
NPT377	Cell Line	OVCAR-3	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[508102]
NPT379	Cell Line	HOP-62	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[508102]
NPT112	Cell Line	MOLT-4	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[508102]
NPT378	Cell Line	NCI/ADR-RES	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[508102]
NPT380	Cell Line	U-251	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[508102]
NPT381	Cell Line	OVCAR-8	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[508102]
NPT382	Cell Line	OVCAR-5	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[508102]
NPT383	Cell Line	SNB-19	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[508102]
NPT385	Cell Line	SR	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[508102]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[508102]
NPT384	Cell Line	TK-10	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[508102]
NPT323	Cell Line	SW-620	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[508102]
NPT455	Cell Line	NCI-H522	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[508102]
NPT387	Cell Line	M14	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[508102]
NPT386	Cell Line	KM12	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[508102]
NPT388	Cell Line	NCI-H322M	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[508102]
NPT389	Cell Line	RPMI-8226	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[508102]
NPT456	Cell Line	OVCAR-4	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[508102]
NPT390	Cell Line	LOX IMVI	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[508102]
NPT391	Cell Line	HCC 2998	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[508102]
NPT148	Cell Line	HCT-15	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[508102]
NPT393	Cell Line	HCT-116	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[508102]
NPT395	Cell Line	SF-268	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[508102]
NPT394	Cell Line	EKVX	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[508102]
NPT83	Cell Line	MCF7	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[508102]
NPT306	Cell Line	PC-3	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[508102]
NPT146	Cell Line	SK-OV-3	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[508102]
NPT396	Cell Line	T47D	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[508102]
NPT398	Cell Line	UACC-62	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[508102]
NPT397	Cell Line	NCI-H460	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[508102]
NPT400	Cell Line	MDA-MB-435	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[508102]
NPT308	Cell Line	CAKI-1	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[508102]
NPT399	Cell Line	SF-295	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[508102]
NPT458	Cell Line	IGROV-1	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[508102]
NPT402	Cell Line	Hs-578T	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[508102]
NPT401	Cell Line	786-0	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[508102]
NPT404	Cell Line	CCRF-CEM	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[508102]
NPT403	Cell Line	UACC-257	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[508102]
NPT405	Cell Line	NCI-H226	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[508102]
NPT139	Cell Line	HT-29	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[508102]
NPT170	Cell Line	SK-MEL-28	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[508102]
NPT406	Cell Line	RXF 393	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[508102]
NPT407	Cell Line	COLO 205	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[508102]

☑ 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 NPC125828 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	5595
0.2-0.3	20887
0.3-0.4	12553
0.4-0.5	2953
0.5-0.6	362
0.6-0.7	55
0.7-0.8	15
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8767	High Similarity	NPC476904
0.875	High Similarity	NPC21773
0.8493	Intermediate Similarity	NPC265789
0.8289	Intermediate Similarity	NPC7214
0.7841	Intermediate Similarity	NPC272732
0.7841	Intermediate Similarity	NPC311164
0.7805	Intermediate Similarity	NPC171639
0.7778	Intermediate Similarity	NPC118329
0.7778	Intermediate Similarity	NPC474122
0.7778	Intermediate Similarity	NPC152039
0.7778	Intermediate Similarity	NPC329782
0.775	Intermediate Similarity	NPC211322
0.7746	Intermediate Similarity	NPC219621
0.7683	Intermediate Similarity	NPC472312
0.7683	Intermediate Similarity	NPC215474
0.7654	Intermediate Similarity	NPC12035
0.7571	Intermediate Similarity	NPC472830
0.7419	Intermediate Similarity	NPC118275
0.7333	Intermediate Similarity	NPC37792
0.7209	Intermediate Similarity	NPC152684
0.7209	Intermediate Similarity	NPC24733
0.7209	Intermediate Similarity	NPC75810
0.7209	Intermediate Similarity	NPC147513
0.7126	Intermediate Similarity	NPC166458
0.7126	Intermediate Similarity	NPC157479
0.7083	Intermediate Similarity	NPC469769
0.7059	Intermediate Similarity	NPC283277
0.6986	Remote Similarity	NPC21781
0.6951	Remote Similarity	NPC259989
0.6951	Remote Similarity	NPC174803
0.6947	Remote Similarity	NPC275686
0.6933	Remote Similarity	NPC474086
0.6818	Remote Similarity	NPC182106
0.6818	Remote Similarity	NPC311769
0.6809	Remote Similarity	NPC476903
0.6804	Remote Similarity	NPC58200
0.6778	Remote Similarity	NPC259252
0.6744	Remote Similarity	NPC257962
0.6744	Remote Similarity	NPC90150
0.6735	Remote Similarity	NPC90538
0.6712	Remote Similarity	NPC470369
0.6712	Remote Similarity	NPC470370
0.6711	Remote Similarity	NPC145715
0.6701	Remote Similarity	NPC474582
0.6667	Remote Similarity	NPC317778
0.6667	Remote Similarity	NPC311809
0.6667	Remote Similarity	NPC140685
0.6667	Remote Similarity	NPC123194
0.6625	Remote Similarity	NPC184919
0.6625	Remote Similarity	NPC138409
0.6623	Remote Similarity	NPC476559
0.6623	Remote Similarity	NPC53276
0.6623	Remote Similarity	NPC473959
0.6591	Remote Similarity	NPC21667
0.6562	Remote Similarity	NPC167419
0.6556	Remote Similarity	NPC56107
0.6548	Remote Similarity	NPC476308
0.6538	Remote Similarity	NPC469970
0.6533	Remote Similarity	NPC475716
0.6533	Remote Similarity	NPC472827
0.6522	Remote Similarity	NPC17518
0.65	Remote Similarity	NPC271640
0.6494	Remote Similarity	NPC472544
0.6489	Remote Similarity	NPC93027
0.6486	Remote Similarity	NPC173815
0.6484	Remote Similarity	NPC43308
0.6471	Remote Similarity	NPC159367
0.6452	Remote Similarity	NPC84171
0.6438	Remote Similarity	NPC470893
0.6436	Remote Similarity	NPC474695
0.64	Remote Similarity	NPC324944
0.64	Remote Similarity	NPC231129
0.64	Remote Similarity	NPC241879
0.6327	Remote Similarity	NPC91604
0.6316	Remote Similarity	NPC476753
0.6316	Remote Similarity	NPC152211
0.6316	Remote Similarity	NPC82919
0.6316	Remote Similarity	NPC28755
0.6316	Remote Similarity	NPC476752
0.63	Remote Similarity	NPC471083
0.63	Remote Similarity	NPC50815
0.63	Remote Similarity	NPC152718
0.6286	Remote Similarity	NPC22765
0.6267	Remote Similarity	NPC475696
0.6267	Remote Similarity	NPC474415
0.6267	Remote Similarity	NPC474528
0.6265	Remote Similarity	NPC476329
0.6263	Remote Similarity	NPC135799
0.625	Remote Similarity	NPC476754
0.6224	Remote Similarity	NPC140300
0.6224	Remote Similarity	NPC474164
0.6224	Remote Similarity	NPC184033
0.622	Remote Similarity	NPC124384
0.622	Remote Similarity	NPC245223
0.6214	Remote Similarity	NPC25340
0.6197	Remote Similarity	NPC200129
0.6176	Remote Similarity	NPC469958
0.617	Remote Similarity	NPC249312
0.6164	Remote Similarity	NPC472828
0.6154	Remote Similarity	NPC471867
0.6145	Remote Similarity	NPC120167
0.6145	Remote Similarity	NPC472543
0.6145	Remote Similarity	NPC473442
0.6143	Remote Similarity	NPC124851
0.6139	Remote Similarity	NPC226509
0.6139	Remote Similarity	NPC247060
0.6133	Remote Similarity	NPC318036
0.6117	Remote Similarity	NPC86906
0.6104	Remote Similarity	NPC474454
0.6104	Remote Similarity	NPC474420
0.6104	Remote Similarity	NPC474455
0.6087	Remote Similarity	NPC86683
0.6087	Remote Similarity	NPC49088
0.6071	Remote Similarity	NPC470078
0.6053	Remote Similarity	NPC474457
0.604	Remote Similarity	NPC474001
0.6038	Remote Similarity	NPC63511
0.6024	Remote Similarity	NPC472831
0.6	Remote Similarity	NPC476682
0.6	Remote Similarity	NPC323445
0.6	Remote Similarity	NPC469770
0.598	Remote Similarity	NPC176012
0.5976	Remote Similarity	NPC176107
0.5962	Remote Similarity	NPC55462
0.5962	Remote Similarity	NPC230677
0.596	Remote Similarity	NPC289140
0.5946	Remote Similarity	NPC476679
0.5946	Remote Similarity	NPC127944
0.5934	Remote Similarity	NPC224072
0.5934	Remote Similarity	NPC39966
0.5926	Remote Similarity	NPC56796
0.5922	Remote Similarity	NPC474583
0.5918	Remote Similarity	NPC243985
0.5918	Remote Similarity	NPC280710
0.5909	Remote Similarity	NPC246904
0.5905	Remote Similarity	NPC46981
0.5904	Remote Similarity	NPC20610
0.5888	Remote Similarity	NPC472313
0.5875	Remote Similarity	NPC477740
0.5865	Remote Similarity	NPC212874
0.5862	Remote Similarity	NPC471468
0.5856	Remote Similarity	NPC473573
0.5854	Remote Similarity	NPC92327
0.5854	Remote Similarity	NPC474456
0.5854	Remote Similarity	NPC176171
0.5833	Remote Similarity	NPC474459
0.5833	Remote Similarity	NPC17810
0.5833	Remote Similarity	NPC79238
0.5833	Remote Similarity	NPC182815
0.581	Remote Similarity	NPC195841
0.581	Remote Similarity	NPC233256
0.5797	Remote Similarity	NPC192529
0.5795	Remote Similarity	NPC25110
0.5794	Remote Similarity	NPC175585
0.5783	Remote Similarity	NPC476135
0.578	Remote Similarity	NPC474452
0.5778	Remote Similarity	NPC57599
0.5765	Remote Similarity	NPC35734
0.5765	Remote Similarity	NPC159577
0.5765	Remote Similarity	NPC282593
0.5765	Remote Similarity	NPC475728
0.5753	Remote Similarity	NPC201713
0.575	Remote Similarity	NPC469728
0.5743	Remote Similarity	NPC240650
0.5741	Remote Similarity	NPC472359
0.5714	Remote Similarity	NPC202189
0.5714	Remote Similarity	NPC160209
0.5698	Remote Similarity	NPC115023
0.5667	Remote Similarity	NPC76931
0.5667	Remote Similarity	NPC307965
0.5667	Remote Similarity	NPC205455
0.5667	Remote Similarity	NPC18603
0.5667	Remote Similarity	NPC186191
0.5652	Remote Similarity	NPC473912
0.5652	Remote Similarity	NPC231986
0.5647	Remote Similarity	NPC269877
0.5647	Remote Similarity	NPC167272
0.5636	Remote Similarity	NPC80834
0.5636	Remote Similarity	NPC469968
0.5634	Remote Similarity	NPC13991
0.5634	Remote Similarity	NPC114239
0.5634	Remote Similarity	NPC296337
0.5634	Remote Similarity	NPC241784
0.5632	Remote Similarity	NPC251705
0.5632	Remote Similarity	NPC303613
0.5632	Remote Similarity	NPC470045
0.5632	Remote Similarity	NPC470044
0.5632	Remote Similarity	NPC474228
0.5632	Remote Similarity	NPC474140
0.5625	Remote Similarity	NPC176621
0.5604	Remote Similarity	NPC170793

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 NPC125828 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	203
0.1-0.2	1133
0.2-0.3	4738
0.3-0.4	2410
0.4-0.5	579
0.5-0.6	84
0.6-0.7	3
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.6543	Remote Similarity	NPD6938	Clinical (unspecified phase)
0.6543	Remote Similarity	NPD6939	Phase 2
0.6463	Remote Similarity	NPD5365	Phase 2
0.6082	Remote Similarity	NPD5771	Approved
0.593	Remote Similarity	NPD5733	Approved
0.5918	Remote Similarity	NPD5769	Clinical (unspecified phase)
0.5914	Remote Similarity	NPD2205	Approved
0.5914	Remote Similarity	NPD2208	Approved
0.5851	Remote Similarity	NPD3099	Discontinued
0.5833	Remote Similarity	NPD8262	Approved
0.5824	Remote Similarity	NPD3035	Approved
0.58	Remote Similarity	NPD1738	Approved
0.5761	Remote Similarity	NPD4701	Clinical (unspecified phase)
0.5761	Remote Similarity	NPD4169	Approved
0.5761	Remote Similarity	NPD4170	Approved
0.5753	Remote Similarity	NPD4834	Discontinued
0.5747	Remote Similarity	NPD4687	Approved
0.5699	Remote Similarity	NPD3527	Clinical (unspecified phase)
0.5699	Remote Similarity	NPD4635	Approved
0.5698	Remote Similarity	NPD5276	Approved
0.5698	Remote Similarity	NPD4243	Approved
0.5658	Remote Similarity	NPD3727	Discontinued
0.5647	Remote Similarity	NPD6922	Approved
0.5647	Remote Similarity	NPD6923	Approved
0.5644	Remote Similarity	NPD5964	Phase 2
0.5644	Remote Similarity	NPD5963	Phase 2
0.5638	Remote Similarity	NPD4544	Approved
0.5612	Remote Similarity	NPD3344	Approved
0.5612	Remote Similarity	NPD3346	Approved
0.5604	Remote Similarity	NPD7155	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