NPASS Compound

Structure

CID15987 OpenBabel06191715342D 23 26 0 0 0 0 0 0 0 0999 V2000 -0.2588 -1.9659 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7934 -0.3912 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 6.0622 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 5.1962 2.0000 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 1.7321 -1.0000 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 0.8660 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 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 0.5000 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 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 2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 2.0000 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 3.4641 -0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 19 1 0 0 0 0 2 19 1 0 0 0 0 3 20 1 0 0 0 0 4 5 2 0 0 0 0 4 6 1 0 0 0 0 5 7 1 0 0 0 0 6 11 2 0 0 0 0 7 13 2 0 0 0 0 8 9 2 0 0 0 0 8 12 1 0 0 0 0 9 19 1 0 0 0 0 10 14 2 0 0 0 0 10 15 1 0 0 0 0 11 13 1 0 0 0 0 11 18 1 0 0 0 0 12 15 2 0 0 0 0 12 17 1 0 0 0 0 13 20 1 0 0 0 0 14 16 1 0 0 0 0 14 21 1 0 0 0 0 15 23 1 0 0 0 0 16 17 2 0 0 0 0 16 18 1 0 0 0 0 17 20 1 0 0 0 0 18 22 2 0 0 0 0 19 23 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	307.12
Volume:	319.23
LogP:	4.065
LogD:	3.44
LogS:	-4.142
# Rotatable Bonds:	0
TPSA:	51.46
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.646
Synthetic Accessibility Score:	2.738
Fsp3:	0.211
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:	-4.668
MDCK Permeability:	2.259386565128807e-05
Pgp-inhibitor:	0.011
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.057
20% Bioavailability (F20%):	0.005
30% Bioavailability (F30%):	0.025

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.249
Plasma Protein Binding (PPB):	98.15682220458984%
Volume Distribution (VD):	0.486
Pgp-substrate:	1.025581955909729%

ADMET: Metabolism

CYP1A2-inhibitor:	0.972
CYP1A2-substrate:	0.79
CYP2C19-inhibitor:	0.875
CYP2C19-substrate:	0.355
CYP2C9-inhibitor:	0.857
CYP2C9-substrate:	0.935
CYP2D6-inhibitor:	0.888
CYP2D6-substrate:	0.756
CYP3A4-inhibitor:	0.668
CYP3A4-substrate:	0.223

ADMET: Excretion

Clearance (CL):	2.308
Half-life (T1/2):	0.176

ADMET: Toxicity

hERG Blockers:	0.047
Human Hepatotoxicity (H-HT):	0.684
Drug-inuced Liver Injury (DILI):	0.63
AMES Toxicity:	0.886
Rat Oral Acute Toxicity:	0.842
Maximum Recommended Daily Dose:	0.914
Skin Sensitization:	0.511
Carcinogencity:	0.952
Eye Corrosion:	0.005
Eye Irritation:	0.903
Respiratory Toxicity:	0.908

Download Data

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

Natural Product: NPC15987

Natural Product ID:	NPC15987
*Common Name:**	Noracronycine
IUPAC Name:	6-hydroxy-3,3,12-trimethylpyrano[2,3-c]acridin-7-one
Synonyms:	Noracronycine
Standard InCHIKey:	CBXBWBNEFPNSDO-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C19H17NO3/c1-19(2)9-8-12-15(23-19)10-14(21)16-17(12)20(3)13-7-5-4-6-11(13)18(16)22/h4-10,21H,1-3H3/p-1
SMILES:	CC1(C)C=Cc2c(cc(c3c2n(C)c2ccccc2c3=O)[O-])O1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL509922
PubChem CID:	5320199
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001253] Quinolines and derivatives [CHEMONTID:0001908] Benzoquinolines [CHEMONTID:0000274] Acridines [CHEMONTID:0001811] Acridones

*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
NPO2715	Murraya paniculata	Species	Rutaceae	Eukaryota	n.a.	twig	n.a.	PMID[24354205]
NPO2715	Murraya paniculata	Species	Rutaceae	Eukaryota	n.a.	leaf	n.a.	PMID[24354205]
NPO2715	Murraya paniculata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO24390	Juniperus rigida	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO2715	Murraya paniculata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24390	Juniperus rigida	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24390	Juniperus rigida	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO2715	Murraya paniculata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO2715	Murraya paniculata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO24390	Juniperus rigida	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6501	Glycosmis cochinchinensis	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2715	Murraya paniculata	Species	Rutaceae	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	58
IC50	4

Activity Type	# Activity
Cell Line	62

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	IC50	>	40000.0	nM	PMID[532805]
NPT319	Cell Line	B16	Mus musculus	IC50	>	40000.0	nM	PMID[532805]
NPT1353	Cell Line	CCRF-HSB-2	Homo sapiens	IC50	>	40000.0	nM	PMID[532805]
NPT1354	Cell Line	TGBC11TKB	Homo sapiens	IC50	>	40000.0	nM	PMID[532805]
NPT368	Cell Line	SN12C	Homo sapiens	GI50	n.a.	25003.45	nM	PMID[532806]
NPT370	Cell Line	NCI-H23	Homo sapiens	GI50	n.a.	25003.45	nM	PMID[532806]
NPT371	Cell Line	UO-31	Homo sapiens	GI50	n.a.	25003.45	nM	PMID[532806]
NPT372	Cell Line	HOP-92	Homo sapiens	GI50	n.a.	25003.45	nM	PMID[532806]
NPT116	Cell Line	HL-60	Homo sapiens	GI50	n.a.	11091.75	nM	PMID[532806]
NPT374	Cell Line	SF-539	Homo sapiens	GI50	n.a.	25003.45	nM	PMID[532806]
NPT373	Cell Line	SK-MEL-5	Homo sapiens	GI50	n.a.	25003.45	nM	PMID[532806]
NPT375	Cell Line	Malme-3M	Homo sapiens	GI50	n.a.	25003.45	nM	PMID[532806]
NPT111	Cell Line	K562	Homo sapiens	GI50	n.a.	25003.45	nM	PMID[532806]
NPT376	Cell Line	A498	Homo sapiens	GI50	n.a.	13458.6	nM	PMID[532806]
NPT377	Cell Line	OVCAR-3	Homo sapiens	GI50	n.a.	25003.45	nM	PMID[532806]
NPT112	Cell Line	MOLT-4	Homo sapiens	GI50	n.a.	6280.58	nM	PMID[532806]
NPT379	Cell Line	HOP-62	Homo sapiens	GI50	n.a.	25003.45	nM	PMID[532806]
NPT378	Cell Line	NCI/ADR-RES	Homo sapiens	GI50	n.a.	25003.45	nM	PMID[532806]
NPT380	Cell Line	U-251	Homo sapiens	GI50	n.a.	25003.45	nM	PMID[532806]
NPT381	Cell Line	OVCAR-8	Homo sapiens	GI50	n.a.	2500.35	nM	PMID[532806]
NPT382	Cell Line	OVCAR-5	Homo sapiens	GI50	n.a.	25003.45	nM	PMID[532806]
NPT572	Cell Line	DMS-273	Homo sapiens	GI50	n.a.	25003.45	nM	PMID[532806]
NPT383	Cell Line	SNB-19	Homo sapiens	GI50	n.a.	9311.08	nM	PMID[532806]
NPT573	Cell Line	M19-MEL	Homo sapiens	GI50	n.a.	25003.45	nM	PMID[532806]
NPT323	Cell Line	SW-620	Homo sapiens	GI50	n.a.	12218.0	nM	PMID[532806]
NPT455	Cell Line	NCI-H522	Homo sapiens	GI50	n.a.	25003.45	nM	PMID[532806]
NPT386	Cell Line	KM12	Homo sapiens	GI50	n.a.	25003.45	nM	PMID[532806]
NPT388	Cell Line	NCI-H322M	Homo sapiens	GI50	n.a.	25003.45	nM	PMID[532806]
NPT574	Cell Line	XF498	Homo sapiens	GI50	n.a.	25003.45	nM	PMID[532806]
NPT389	Cell Line	RPMI-8226	Homo sapiens	GI50	n.a.	25003.45	nM	PMID[532806]
NPT456	Cell Line	OVCAR-4	Homo sapiens	GI50	n.a.	25003.45	nM	PMID[532806]
NPT390	Cell Line	LOX IMVI	Homo sapiens	GI50	n.a.	25003.45	nM	PMID[532806]
NPT168	Cell Line	P388	Mus musculus	GI50	n.a.	25003.45	nM	PMID[532806]
NPT575	Cell Line	KM-20L2	Homo sapiens	GI50	n.a.	10162.49	nM	PMID[532806]
NPT147	Cell Line	SK-MEL-2	Homo sapiens	GI50	n.a.	25003.45	nM	PMID[532806]
NPT391	Cell Line	HCC 2998	Homo sapiens	GI50	n.a.	25003.45	nM	PMID[532806]
NPT81	Cell Line	A549	Homo sapiens	GI50	n.a.	25003.45	nM	PMID[532806]
NPT392	Cell Line	SNB-75	Homo sapiens	GI50	n.a.	16826.74	nM	PMID[532806]
NPT148	Cell Line	HCT-15	Homo sapiens	GI50	n.a.	25003.45	nM	PMID[532806]
NPT393	Cell Line	HCT-116	Homo sapiens	GI50	n.a.	25003.45	nM	PMID[532806]
NPT395	Cell Line	SF-268	Homo sapiens	GI50	n.a.	25003.45	nM	PMID[532806]
NPT394	Cell Line	EKVX	Homo sapiens	GI50	n.a.	21086.28	nM	PMID[532806]
NPT83	Cell Line	MCF7	Homo sapiens	GI50	n.a.	25003.45	nM	PMID[532806]
NPT146	Cell Line	SK-OV-3	Homo sapiens	GI50	n.a.	25003.45	nM	PMID[532806]
NPT576	Cell Line	DMS-114	Homo sapiens	GI50	n.a.	25003.45	nM	PMID[532806]
NPT397	Cell Line	NCI-H460	Homo sapiens	GI50	n.a.	25003.45	nM	PMID[532806]
NPT308	Cell Line	CAKI-1	Homo sapiens	GI50	n.a.	3047.89	nM	PMID[532806]
NPT398	Cell Line	UACC-62	Homo sapiens	GI50	n.a.	25003.45	nM	PMID[532806]
NPT399	Cell Line	SF-295	Homo sapiens	GI50	n.a.	25003.45	nM	PMID[532806]
NPT552	Cell Line	P388/ADR	Mus musculus	GI50	n.a.	25003.45	nM	PMID[532806]
NPT458	Cell Line	IGROV-1	Homo sapiens	GI50	n.a.	25003.45	nM	PMID[532806]
NPT403	Cell Line	UACC-257	Homo sapiens	GI50	n.a.	25003.45	nM	PMID[532806]
NPT578	Cell Line	SNB-78	Homo sapiens	GI50	n.a.	25003.45	nM	PMID[532806]
NPT579	Cell Line	DLD-1	Homo sapiens	GI50	n.a.	19364.22	nM	PMID[532806]
NPT404	Cell Line	CCRF-CEM	Homo sapiens	GI50	n.a.	25003.45	nM	PMID[532806]
NPT139	Cell Line	HT-29	Homo sapiens	GI50	n.a.	25003.45	nM	PMID[532806]
NPT405	Cell Line	NCI-H226	Homo sapiens	GI50	n.a.	25003.45	nM	PMID[532806]
NPT170	Cell Line	SK-MEL-28	Homo sapiens	GI50	n.a.	25003.45	nM	PMID[532806]
NPT406	Cell Line	RXF 393	Homo sapiens	GI50	n.a.	10162.49	nM	PMID[532806]
NPT407	Cell Line	COLO 205	Homo sapiens	GI50	n.a.	25003.45	nM	PMID[532806]
NPT732	Cell Line	HOP-18	Homo sapiens	GI50	n.a.	13708.82	nM	PMID[532806]
NPT738	Cell Line	SN12K1	Homo sapiens	GI50	n.a.	25003.45	nM	PMID[532806]

☑ 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 NPC15987 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	502
0.1-0.2	3086
0.2-0.3	11904
0.3-0.4	4784
0.4-0.5	9099
0.5-0.6	9789
0.6-0.7	3154
0.7-0.8	316
0.8-0.85	31
0.85-0.9	14
0.9-0.95	12
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
0.9667	High Similarity	NPC234933
0.9563	High Similarity	NPC288759
0.9462	High Similarity	NPC198160
0.9459	High Similarity	NPC301292
0.9459	High Similarity	NPC313112
0.9389	High Similarity	NPC114039
0.9389	High Similarity	NPC206109
0.9316	High Similarity	NPC305542
0.9316	High Similarity	NPC116178
0.9293	High Similarity	NPC241263
0.9267	High Similarity	NPC217903
0.9267	High Similarity	NPC321166
0.9267	High Similarity	NPC30749
0.8964	High Similarity	NPC218303
0.8953	High Similarity	NPC212123
0.8939	High Similarity	NPC329830
0.8939	High Similarity	NPC298320
0.8923	High Similarity	NPC176113
0.8913	High Similarity	NPC1820
0.8719	High Similarity	NPC13249
0.8673	High Similarity	NPC295479
0.8673	High Similarity	NPC220241
0.8528	High Similarity	NPC474366
0.8526	High Similarity	NPC170333
0.8478	Intermediate Similarity	NPC327005
0.8416	Intermediate Similarity	NPC134702
0.8416	Intermediate Similarity	NPC182853
0.8358	Intermediate Similarity	NPC148391
0.8324	Intermediate Similarity	NPC204867
0.8293	Intermediate Similarity	NPC118189
0.8293	Intermediate Similarity	NPC7560
0.8274	Intermediate Similarity	NPC133156
0.8218	Intermediate Similarity	NPC114468
0.8204	Intermediate Similarity	NPC76478
0.8177	Intermediate Similarity	NPC2905
0.8177	Intermediate Similarity	NPC299582
0.8128	Intermediate Similarity	NPC268223
0.8048	Intermediate Similarity	NPC285254
0.7971	Intermediate Similarity	NPC87560
0.7971	Intermediate Similarity	NPC195120
0.7857	Intermediate Similarity	NPC471825
0.781	Intermediate Similarity	NPC469439
0.781	Intermediate Similarity	NPC118154
0.781	Intermediate Similarity	NPC157983
0.7772	Intermediate Similarity	NPC41216
0.7737	Intermediate Similarity	NPC127082
0.7737	Intermediate Similarity	NPC9475
0.7667	Intermediate Similarity	NPC144691
0.7633	Intermediate Similarity	NPC25961
0.7556	Intermediate Similarity	NPC38219
0.7525	Intermediate Similarity	NPC469437
0.75	Intermediate Similarity	NPC129578
0.7486	Intermediate Similarity	NPC305355
0.7486	Intermediate Similarity	NPC475680
0.7459	Intermediate Similarity	NPC219915
0.7444	Intermediate Similarity	NPC64908
0.7444	Intermediate Similarity	NPC147688
0.7444	Intermediate Similarity	NPC156590
0.7444	Intermediate Similarity	NPC118840
0.7444	Intermediate Similarity	NPC205006
0.7436	Intermediate Similarity	NPC309692
0.7432	Intermediate Similarity	NPC110303
0.7432	Intermediate Similarity	NPC23728
0.7403	Intermediate Similarity	NPC59739
0.7403	Intermediate Similarity	NPC214236
0.7403	Intermediate Similarity	NPC11561
0.7403	Intermediate Similarity	NPC78803
0.7403	Intermediate Similarity	NPC293852
0.7403	Intermediate Similarity	NPC62840
0.7403	Intermediate Similarity	NPC144499
0.7403	Intermediate Similarity	NPC226636
0.7403	Intermediate Similarity	NPC299080
0.7403	Intermediate Similarity	NPC217083
0.7391	Intermediate Similarity	NPC132592
0.7391	Intermediate Similarity	NPC160821
0.7389	Intermediate Similarity	NPC270883
0.7389	Intermediate Similarity	NPC172986
0.7389	Intermediate Similarity	NPC235239
0.7389	Intermediate Similarity	NPC69769
0.7389	Intermediate Similarity	NPC261227
0.7377	Intermediate Similarity	NPC470647
0.7377	Intermediate Similarity	NPC88964
0.7377	Intermediate Similarity	NPC246948
0.7377	Intermediate Similarity	NPC475052
0.7377	Intermediate Similarity	NPC176229
0.7377	Intermediate Similarity	NPC111786
0.7377	Intermediate Similarity	NPC20488
0.7377	Intermediate Similarity	NPC67805
0.7377	Intermediate Similarity	NPC301276
0.7377	Intermediate Similarity	NPC214774
0.7377	Intermediate Similarity	NPC195621
0.7377	Intermediate Similarity	NPC267375
0.7377	Intermediate Similarity	NPC83357
0.7377	Intermediate Similarity	NPC312973
0.7377	Intermediate Similarity	NPC142405
0.7377	Intermediate Similarity	NPC54577
0.7363	Intermediate Similarity	NPC166138
0.7363	Intermediate Similarity	NPC18585
0.7363	Intermediate Similarity	NPC106985
0.7348	Intermediate Similarity	NPC103362
0.7348	Intermediate Similarity	NPC110969
0.734	Intermediate Similarity	NPC93653
0.7337	Intermediate Similarity	NPC79469
0.7337	Intermediate Similarity	NPC283234
0.7337	Intermediate Similarity	NPC237635
0.7337	Intermediate Similarity	NPC97716
0.7337	Intermediate Similarity	NPC473077
0.7337	Intermediate Similarity	NPC24673
0.7337	Intermediate Similarity	NPC104406
0.7337	Intermediate Similarity	NPC296998
0.7337	Intermediate Similarity	NPC201731
0.7333	Intermediate Similarity	NPC96565
0.7333	Intermediate Similarity	NPC303633
0.7333	Intermediate Similarity	NPC216978
0.7333	Intermediate Similarity	NPC220062
0.7333	Intermediate Similarity	NPC55018
0.7333	Intermediate Similarity	NPC301217
0.7322	Intermediate Similarity	NPC209040
0.7322	Intermediate Similarity	NPC257236
0.7322	Intermediate Similarity	NPC234629
0.7322	Intermediate Similarity	NPC278175
0.7322	Intermediate Similarity	NPC311741
0.7297	Intermediate Similarity	NPC266572
0.7297	Intermediate Similarity	NPC161191
0.7297	Intermediate Similarity	NPC6511
0.7297	Intermediate Similarity	NPC296869
0.7293	Intermediate Similarity	NPC241100
0.7293	Intermediate Similarity	NPC159275
0.7293	Intermediate Similarity	NPC150522
0.7291	Intermediate Similarity	NPC264938
0.7289	Intermediate Similarity	NPC151171
0.7283	Intermediate Similarity	NPC477955
0.7278	Intermediate Similarity	NPC201395
0.7268	Intermediate Similarity	NPC316816
0.7268	Intermediate Similarity	NPC478086
0.7268	Intermediate Similarity	NPC310130
0.7268	Intermediate Similarity	NPC164980
0.7268	Intermediate Similarity	NPC149026
0.7268	Intermediate Similarity	NPC68104
0.7268	Intermediate Similarity	NPC257097
0.7268	Intermediate Similarity	NPC150408
0.7268	Intermediate Similarity	NPC175504
0.7268	Intermediate Similarity	NPC91560
0.7268	Intermediate Similarity	NPC221432
0.7268	Intermediate Similarity	NPC39329
0.7268	Intermediate Similarity	NPC75049
0.7268	Intermediate Similarity	NPC17677
0.7268	Intermediate Similarity	NPC83019
0.7268	Intermediate Similarity	NPC214166
0.7268	Intermediate Similarity	NPC143896
0.7268	Intermediate Similarity	NPC169591
0.7264	Intermediate Similarity	NPC45389
0.726	Intermediate Similarity	NPC473449
0.7253	Intermediate Similarity	NPC282300
0.7253	Intermediate Similarity	NPC14871
0.7253	Intermediate Similarity	NPC3188
0.7248	Intermediate Similarity	NPC251071
0.7243	Intermediate Similarity	NPC166757
0.7243	Intermediate Similarity	NPC140120
0.7243	Intermediate Similarity	NPC180477
0.7243	Intermediate Similarity	NPC14001
0.7238	Intermediate Similarity	NPC78913
0.7238	Intermediate Similarity	NPC18260
0.7238	Intermediate Similarity	NPC53181
0.7238	Intermediate Similarity	NPC217186
0.7228	Intermediate Similarity	NPC473013
0.7228	Intermediate Similarity	NPC131568
0.7228	Intermediate Similarity	NPC131579
0.7228	Intermediate Similarity	NPC469953
0.7228	Intermediate Similarity	NPC197252
0.7228	Intermediate Similarity	NPC319752
0.7228	Intermediate Similarity	NPC473015
0.7228	Intermediate Similarity	NPC236766
0.7222	Intermediate Similarity	NPC157855
0.7222	Intermediate Similarity	NPC228661
0.722	Intermediate Similarity	NPC204580
0.7219	Intermediate Similarity	NPC188403
0.7219	Intermediate Similarity	NPC29777
0.7219	Intermediate Similarity	NPC120105
0.7219	Intermediate Similarity	NPC471115
0.7219	Intermediate Similarity	NPC472633
0.7219	Intermediate Similarity	NPC101957
0.7213	Intermediate Similarity	NPC37496
0.7213	Intermediate Similarity	NPC177354
0.7213	Intermediate Similarity	NPC147145
0.7213	Intermediate Similarity	NPC125855
0.7213	Intermediate Similarity	NPC76338
0.7213	Intermediate Similarity	NPC64915
0.7213	Intermediate Similarity	NPC265040
0.7213	Intermediate Similarity	NPC296917
0.7213	Intermediate Similarity	NPC1089
0.7213	Intermediate Similarity	NPC306829
0.7213	Intermediate Similarity	NPC194432
0.7213	Intermediate Similarity	NPC324134
0.7213	Intermediate Similarity	NPC167624
0.7213	Intermediate Similarity	NPC32739
0.7213	Intermediate Similarity	NPC148757
0.7213	Intermediate Similarity	NPC166482
0.7213	Intermediate Similarity	NPC66515
0.7213	Intermediate Similarity	NPC220998

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 NPC15987 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	339
0.1-0.2	685
0.2-0.3	985
0.3-0.4	1502
0.4-0.5	2649
0.5-0.6	2159
0.6-0.7	744
0.7-0.8	82
0.8-0.85	5
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8195	Intermediate Similarity	NPD2899	Discontinued
0.795	Intermediate Similarity	NPD7064	Clinical (unspecified phase)
0.7923	Intermediate Similarity	NPD3949	Clinical (unspecified phase)
0.7822	Intermediate Similarity	NPD3298	Approved
0.7673	Intermediate Similarity	NPD7566	Clinical (unspecified phase)
0.7662	Intermediate Similarity	NPD6874	Approved
0.7662	Intermediate Similarity	NPD3297	Approved
0.7594	Intermediate Similarity	NPD5496	Approved
0.7577	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7538	Intermediate Similarity	NPD5937	Approved
0.7533	Intermediate Similarity	NPD6525	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD5940	Clinical (unspecified phase)
0.7475	Intermediate Similarity	NPD6608	Clinical (unspecified phase)
0.7474	Intermediate Similarity	NPD5183	Approved
0.7474	Intermediate Similarity	NPD5186	Approved
0.7465	Intermediate Similarity	NPD6198	Phase 1
0.7404	Intermediate Similarity	NPD7584	Approved
0.7339	Intermediate Similarity	NPD8461	Discontinued
0.7322	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7291	Intermediate Similarity	NPD4360	Phase 2
0.7291	Intermediate Similarity	NPD4363	Phase 3
0.7282	Intermediate Similarity	NPD3793	Phase 3
0.7268	Intermediate Similarity	NPD3446	Phase 1
0.7263	Intermediate Similarity	NPD955	Approved
0.7259	Intermediate Similarity	NPD6104	Discontinued
0.722	Intermediate Similarity	NPD7238	Clinical (unspecified phase)
0.7171	Intermediate Similarity	NPD4361	Phase 2
0.7171	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7162	Intermediate Similarity	NPD7654	Discontinued
0.7136	Intermediate Similarity	NPD4979	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7129	Intermediate Similarity	NPD956	Clinical (unspecified phase)
0.7118	Intermediate Similarity	NPD1483	Discontinued
0.7107	Intermediate Similarity	NPD6020	Phase 2
0.7107	Intermediate Similarity	NPD5521	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD4539	Phase 1
0.7071	Intermediate Similarity	NPD5900	Clinical (unspecified phase)
0.7062	Intermediate Similarity	NPD4465	Phase 2
0.7062	Intermediate Similarity	NPD4467	Phase 2
0.7056	Intermediate Similarity	NPD5860	Discontinued
0.7054	Intermediate Similarity	NPD4981	Phase 2
0.7042	Intermediate Similarity	NPD7585	Approved
0.7041	Intermediate Similarity	NPD2246	Approved
0.7041	Intermediate Similarity	NPD2248	Approved
0.7037	Intermediate Similarity	NPD6585	Discontinued
0.7033	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD3925	Approved
0.7	Intermediate Similarity	NPD3783	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD7411	Suspended
0.6995	Remote Similarity	NPD7583	Approved
0.6995	Remote Similarity	NPD1549	Phase 2
0.6977	Remote Similarity	NPD5726	Clinical (unspecified phase)
0.6961	Remote Similarity	NPD1898	Discontinued
0.6961	Remote Similarity	NPD5620	Clinical (unspecified phase)
0.695	Remote Similarity	NPD6654	Clinical (unspecified phase)
0.6947	Remote Similarity	NPD4380	Phase 2
0.694	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.694	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6927	Remote Similarity	NPD5417	Clinical (unspecified phase)
0.6927	Remote Similarity	NPD5928	Phase 1
0.6926	Remote Similarity	NPD7417	Discontinued
0.692	Remote Similarity	NPD7186	Phase 3
0.6915	Remote Similarity	NPD5637	Discontinued
0.6912	Remote Similarity	NPD4515	Suspended
0.6911	Remote Similarity	NPD5889	Approved
0.6911	Remote Similarity	NPD2366	Approved
0.6911	Remote Similarity	NPD5890	Approved
0.6909	Remote Similarity	NPD1926	Approved
0.69	Remote Similarity	NPD7479	Phase 2
0.6897	Remote Similarity	NPD6021	Clinical (unspecified phase)
0.6891	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.689	Remote Similarity	NPD6621	Clinical (unspecified phase)
0.6889	Remote Similarity	NPD1240	Approved
0.6887	Remote Similarity	NPD6795	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD7071	Clinical (unspecified phase)
0.6886	Remote Similarity	NPD6625	Approved
0.6885	Remote Similarity	NPD2796	Approved
0.6883	Remote Similarity	NPD4613	Phase 2
0.6875	Remote Similarity	NPD7577	Discontinued
0.6872	Remote Similarity	NPD8067	Phase 3
0.6866	Remote Similarity	NPD1945	Phase 1
0.6866	Remote Similarity	NPD6211	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD4668	Phase 2
0.6854	Remote Similarity	NPD7597	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6837	Remote Similarity	NPD7043	Discontinued
0.6831	Remote Similarity	NPD1510	Phase 2
0.6828	Remote Similarity	NPD6199	Discontinued
0.6822	Remote Similarity	NPD5102	Clinical (unspecified phase)
0.6821	Remote Similarity	NPD6533	Clinical (unspecified phase)
0.6821	Remote Similarity	NPD7075	Discontinued
0.682	Remote Similarity	NPD4997	Clinical (unspecified phase)
0.6813	Remote Similarity	NPD1607	Approved
0.6812	Remote Similarity	NPD7922	Phase 1
0.6806	Remote Similarity	NPD3229	Phase 2
0.6806	Remote Similarity	NPD2907	Approved
0.6806	Remote Similarity	NPD2906	Approved
0.6798	Remote Similarity	NPD6962	Phase 2
0.6788	Remote Similarity	NPD6844	Discontinued
0.6782	Remote Similarity	NPD6293	Clinical (unspecified phase)
0.6781	Remote Similarity	NPD6790	Phase 1
0.6774	Remote Similarity	NPD2654	Approved
0.6766	Remote Similarity	NPD3965	Phase 1
0.6765	Remote Similarity	NPD7546	Discontinued
0.6761	Remote Similarity	NPD6321	Discontinued
0.6753	Remote Similarity	NPD7819	Suspended
0.6753	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.675	Remote Similarity	NPD7449	Clinical (unspecified phase)
0.6745	Remote Similarity	NPD7810	Phase 3
0.6745	Remote Similarity	NPD7811	Phase 3
0.6744	Remote Similarity	NPD6250	Discontinued
0.6742	Remote Similarity	NPD6744	Clinical (unspecified phase)
0.6737	Remote Similarity	NPD5488	Discontinued
0.6735	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6731	Remote Similarity	NPD6656	Clinical (unspecified phase)
0.6729	Remote Similarity	NPD7627	Approved
0.6729	Remote Similarity	NPD7626	Approved
0.6728	Remote Similarity	NPD6593	Clinical (unspecified phase)
0.6728	Remote Similarity	NPD4082	Approved
0.6724	Remote Similarity	NPD2300	Clinical (unspecified phase)
0.6724	Remote Similarity	NPD4846	Phase 2
0.6723	Remote Similarity	NPD8367	Approved
0.6719	Remote Similarity	NPD6357	Discontinued
0.6717	Remote Similarity	NPD6457	Approved
0.6717	Remote Similarity	NPD2821	Approved
0.6712	Remote Similarity	NPD683	Approved
0.6703	Remote Similarity	NPD3140	Approved
0.6703	Remote Similarity	NPD3142	Approved
0.6702	Remote Similarity	NPD3295	Clinical (unspecified phase)
0.6701	Remote Similarity	NPD6801	Discontinued
0.67	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6698	Remote Similarity	NPD5071	Phase 2
0.6696	Remote Similarity	NPD5433	Clinical (unspecified phase)
0.6683	Remote Similarity	NPD5896	Clinical (unspecified phase)
0.6682	Remote Similarity	NPD6296	Discontinued
0.6682	Remote Similarity	NPD7263	Phase 2
0.668	Remote Similarity	NPD8492	Approved
0.6667	Remote Similarity	NPD7560	Approved
0.6667	Remote Similarity	NPD4373	Phase 2
0.6667	Remote Similarity	NPD3863	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5610	Approved
0.6667	Remote Similarity	NPD3251	Approved
0.6652	Remote Similarity	NPD4377	Discontinued
0.665	Remote Similarity	NPD8005	Clinical (unspecified phase)
0.665	Remote Similarity	NPD1913	Phase 1
0.665	Remote Similarity	NPD3749	Approved
0.6649	Remote Similarity	NPD3750	Approved
0.6636	Remote Similarity	NPD7174	Clinical (unspecified phase)
0.6633	Remote Similarity	NPD2247	Approved
0.6633	Remote Similarity	NPD2249	Approved
0.6632	Remote Similarity	NPD7213	Phase 3
0.6632	Remote Similarity	NPD7212	Phase 2
0.6632	Remote Similarity	NPD1511	Approved
0.6623	Remote Similarity	NPD7031	Phase 1
0.6622	Remote Similarity	NPD7858	Clinical (unspecified phase)
0.662	Remote Similarity	NPD5194	Approved
0.662	Remote Similarity	NPD5196	Approved
0.662	Remote Similarity	NPD3802	Phase 3
0.662	Remote Similarity	NPD5197	Approved
0.6618	Remote Similarity	NPD6496	Clinical (unspecified phase)
0.6618	Remote Similarity	NPD3823	Discontinued
0.6616	Remote Similarity	NPD3252	Approved
0.6615	Remote Similarity	NPD1934	Approved
0.6609	Remote Similarity	NPD4952	Phase 3
0.6606	Remote Similarity	NPD5143	Clinical (unspecified phase)
0.6606	Remote Similarity	NPD7301	Phase 3
0.6601	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6599	Remote Similarity	NPD7803	Approved
0.6599	Remote Similarity	NPD7768	Phase 2
0.6597	Remote Similarity	NPD7447	Phase 1
0.6594	Remote Similarity	NPD3899	Clinical (unspecified phase)
0.659	Remote Similarity	NPD4456	Clinical (unspecified phase)
0.6589	Remote Similarity	NPD5547	Clinical (unspecified phase)
0.6583	Remote Similarity	NPD5823	Approved
0.6582	Remote Similarity	NPD2801	Approved
0.6574	Remote Similarity	NPD7316	Discontinued
0.6574	Remote Similarity	NPD5006	Approved
0.6574	Remote Similarity	NPD5005	Approved
0.6573	Remote Similarity	NPD5195	Discontinued
0.6573	Remote Similarity	NPD5515	Phase 2
0.6571	Remote Similarity	NPD5871	Discontinued
0.6567	Remote Similarity	NPD5242	Approved
0.6562	Remote Similarity	NPD1512	Approved
0.6561	Remote Similarity	NPD6567	Clinical (unspecified phase)
0.6561	Remote Similarity	NPD5416	Discontinued
0.6558	Remote Similarity	NPD2339	Phase 3
0.6558	Remote Similarity	NPD7255	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD5603	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD7177	Discontinued
0.655	Remote Similarity	NPD6959	Discontinued
0.655	Remote Similarity	NPD4986	Clinical (unspecified phase)
0.6545	Remote Similarity	NPD6799	Approved
0.654	Remote Similarity	NPD5587	Approved
0.6538	Remote Similarity	NPD3153	Approved
0.6538	Remote Similarity	NPD3154	Approved
0.6535	Remote Similarity	NPD3451	Clinical (unspecified phase)
0.6535	Remote Similarity	NPD3912	Discontinued
0.6533	Remote Similarity	NPD7395	Discontinued
0.6532	Remote Similarity	NPD7225	Discontinued
0.6532	Remote Similarity	NPD7178	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