NPASS Compound

Structure

CID15919 OpenBabel06191715342D 21 26 0 0 1 0 0 0 0 0999 V2000 -0.8699 -1.7400 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1884 -2.2916 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5070 -3.4800 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5070 -1.7400 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5068 -1.7401 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0001 -3.4800 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5992 -2.6100 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7535 -3.0450 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7535 -2.1750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5069 -0.8701 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.2604 -3.0450 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2604 -2.1750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7534 -2.1751 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.7534 -0.4350 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -0.8700 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0001 -1.7400 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.7534 -3.0451 0.0000 N 0 0 3 0 0 0 0 0 0 0 0 0 -2.2379 -0.4480 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.0878 -3.3138 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.0878 -1.9061 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 2 1 0 0 0 0 2 17 1 0 0 0 0 3 8 2 0 0 0 0 3 11 1 0 0 0 0 4 9 2 0 0 0 0 4 12 1 0 0 0 0 5 10 1 0 0 0 0 5 13 1 0 0 0 0 6 8 1 0 0 0 0 6 17 1 0 0 0 0 7 19 1 0 0 0 0 7 20 1 0 0 0 0 8 9 1 0 0 0 0 9 16 1 0 0 0 0 10 14 1 0 0 0 0 10 18 1 1 0 0 0 11 12 2 0 0 0 0 11 19 1 0 0 0 0 12 20 1 0 0 0 0 13 16 1 6 0 0 0 13 17 1 0 0 0 0 14 15 1 0 0 0 0 14 21 1 6 0 0 0 15 16 1 6 0 0 0 15 21 1 0 0 0 0 16 1 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	287.12
Volume:	272.202
LogP:	1.183
LogD:	0.93
LogS:	-3.98
# Rotatable Bonds:	0
TPSA:	54.46
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	6
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.714
Synthetic Accessibility Score:	5.123
Fsp3:	0.625
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.298
MDCK Permeability:	1.3892618881072849e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.996
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.017
30% Bioavailability (F30%):	0.908

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.99
Plasma Protein Binding (PPB):	33.90498352050781%
Volume Distribution (VD):	2.751
Pgp-substrate:	50.04595947265625%

ADMET: Metabolism

CYP1A2-inhibitor:	0.335
CYP1A2-substrate:	0.44
CYP2C19-inhibitor:	0.142
CYP2C19-substrate:	0.823
CYP2C9-inhibitor:	0.023
CYP2C9-substrate:	0.311
CYP2D6-inhibitor:	0.948
CYP2D6-substrate:	0.807
CYP3A4-inhibitor:	0.632
CYP3A4-substrate:	0.579

ADMET: Excretion

Clearance (CL):	16.526
Half-life (T1/2):	0.543

ADMET: Toxicity

hERG Blockers:	0.451
Human Hepatotoxicity (H-HT):	0.623
Drug-inuced Liver Injury (DILI):	0.163
AMES Toxicity:	0.111
Rat Oral Acute Toxicity:	0.604
Maximum Recommended Daily Dose:	0.907
Skin Sensitization:	0.099
Carcinogencity:	0.804
Eye Corrosion:	0.003
Eye Irritation:	0.011
Respiratory Toxicity:	0.922

Download Data

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

Natural Product: NPC15919

Natural Product ID:	NPC15919
*Common Name:**	WWSZBGJLESQTHB-DMHMKPBJSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	WWSZBGJLESQTHB-DMHMKPBJSA-N
Standard InCHI:	InChI=1S/C16H17NO4/c18-10-5-13-16(15-14(10)21-15)1-2-17(13)6-8-3-11-12(4-9(8)16)20-7-19-11/h3-4,10,13-15,18H,1-2,5-7H2/t10-,13-,14+,15+,16+/m1/s1
SMILES:	O[C@@H]1C[C@H]2N3CC[C@]2([C@@H]2[C@H]1O2)c1c(C3)cc2c(c1)OCO2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1997786
PubChem CID:	398936
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids and derivatives [CHEMONTID:0001775] Amaryllidaceae alkaloids [CHEMONTID:0004123] Crinine- and Haemanthamine-type amaryllidaceae 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
NPO24293	Neorautanenia mitis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16562843]
NPO24293	Neorautanenia mitis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24293	Neorautanenia mitis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10342	Crinum americanum	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23091	Halocarpus bidwillii	Species	Podocarpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21398	Jasminum laurifolium f. nitidum	Species	Oleaceae	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

Activity Type	# Activity
Cell Line	58

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT367	Cell Line	MDA-N	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[559618]
NPT368	Cell Line	SN12C	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[559618]
NPT369	Cell Line	ACHN	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[559618]
NPT370	Cell Line	NCI-H23	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[559618]
NPT371	Cell Line	UO-31	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[559618]
NPT372	Cell Line	HOP-92	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[559618]
NPT116	Cell Line	HL-60	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[559618]
NPT90	Cell Line	DU-145	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[559618]
NPT374	Cell Line	SF-539	Homo sapiens	GI50	n.a.	17.78	nM	PMID[559618]
NPT373	Cell Line	SK-MEL-5	Homo sapiens	GI50	n.a.	10.0	nM	PMID[559618]
NPT375	Cell Line	Malme-3M	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[559618]
NPT376	Cell Line	A498	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[559618]
NPT111	Cell Line	K562	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[559618]
NPT377	Cell Line	OVCAR-3	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[559618]
NPT112	Cell Line	MOLT-4	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[559618]
NPT378	Cell Line	NCI/ADR-RES	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[559618]
NPT379	Cell Line	HOP-62	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[559618]
NPT380	Cell Line	U-251	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[559618]
NPT382	Cell Line	OVCAR-5	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[559618]
NPT381	Cell Line	OVCAR-8	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[559618]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[559618]
NPT383	Cell Line	SNB-19	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[559618]
NPT384	Cell Line	TK-10	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[559618]
NPT323	Cell Line	SW-620	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[559618]
NPT455	Cell Line	NCI-H522	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[559618]
NPT386	Cell Line	KM12	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[559618]
NPT387	Cell Line	M14	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[559618]
NPT388	Cell Line	NCI-H322M	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[559618]
NPT389	Cell Line	RPMI-8226	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[559618]
NPT456	Cell Line	OVCAR-4	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[559618]
NPT390	Cell Line	LOX IMVI	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[559618]
NPT457	Cell Line	BT-549	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[559618]
NPT147	Cell Line	SK-MEL-2	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[559618]
NPT81	Cell Line	A549	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[559618]
NPT391	Cell Line	HCC 2998	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[559618]
NPT392	Cell Line	SNB-75	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[559618]
NPT148	Cell Line	HCT-15	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[559618]
NPT393	Cell Line	HCT-116	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[559618]
NPT395	Cell Line	SF-268	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[559618]
NPT306	Cell Line	PC-3	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[559618]
NPT83	Cell Line	MCF7	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[559618]
NPT394	Cell Line	EKVX	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[559618]
NPT146	Cell Line	SK-OV-3	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[559618]
NPT397	Cell Line	NCI-H460	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[559618]
NPT398	Cell Line	UACC-62	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[559618]
NPT308	Cell Line	CAKI-1	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[559618]
NPT400	Cell Line	MDA-MB-435	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[559618]
NPT458	Cell Line	IGROV-1	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[559618]
NPT399	Cell Line	SF-295	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[559618]
NPT402	Cell Line	Hs-578T	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[559618]
NPT403	Cell Line	UACC-257	Homo sapiens	GI50	n.a.	90364.95	nM	PMID[559618]
NPT401	Cell Line	786-0	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[559618]
NPT404	Cell Line	CCRF-CEM	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[559618]
NPT405	Cell Line	NCI-H226	Homo sapiens	GI50	n.a.	27.1	nM	PMID[559618]
NPT170	Cell Line	SK-MEL-28	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[559618]
NPT139	Cell Line	HT-29	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[559618]
NPT406	Cell Line	RXF 393	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[559618]
NPT407	Cell Line	COLO 205	Homo sapiens	GI50	n.a.	10.0	nM	PMID[559618]

☑ 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 NPC15919 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	350
0.1-0.2	1430
0.2-0.3	4248
0.3-0.4	11379
0.4-0.5	9018
0.5-0.6	12300
0.6-0.7	3252
0.7-0.8	605
0.8-0.85	75
0.85-0.9	32
0.9-0.95	5
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9689	High Similarity	NPC311991
0.963	High Similarity	NPC65403
0.9464	High Similarity	NPC9867
0.9277	High Similarity	NPC187678
0.9091	High Similarity	NPC190332
0.9091	High Similarity	NPC100566
0.9091	High Similarity	NPC181653
0.9036	High Similarity	NPC266176
0.9036	High Similarity	NPC82533
0.9036	High Similarity	NPC475686
0.9036	High Similarity	NPC158148
0.9036	High Similarity	NPC58766
0.9036	High Similarity	NPC290759
0.9024	High Similarity	NPC320104
0.9	High Similarity	NPC244554
0.8982	High Similarity	NPC474475
0.8935	High Similarity	NPC304675
0.8929	High Similarity	NPC470739
0.8929	High Similarity	NPC477640
0.8929	High Similarity	NPC225597
0.8902	High Similarity	NPC97072
0.8902	High Similarity	NPC215829
0.8882	High Similarity	NPC474470
0.8882	High Similarity	NPC237044
0.8869	High Similarity	NPC75958
0.883	High Similarity	NPC474325
0.883	High Similarity	NPC294790
0.883	High Similarity	NPC148693
0.883	High Similarity	NPC118633
0.8779	High Similarity	NPC474745
0.8736	High Similarity	NPC475981
0.8736	High Similarity	NPC474746
0.8659	High Similarity	NPC78733
0.8639	High Similarity	NPC474324
0.8639	High Similarity	NPC57812
0.8631	High Similarity	NPC247972
0.8588	High Similarity	NPC475845
0.858	High Similarity	NPC476002
0.8571	High Similarity	NPC218614
0.8571	High Similarity	NPC275132
0.8547	High Similarity	NPC2314
0.8538	High Similarity	NPC474708
0.8531	High Similarity	NPC230098
0.8529	High Similarity	NPC252960
0.8452	Intermediate Similarity	NPC205167
0.8452	Intermediate Similarity	NPC4304
0.8452	Intermediate Similarity	NPC249274
0.8391	Intermediate Similarity	NPC49353
0.8383	Intermediate Similarity	NPC234392
0.8383	Intermediate Similarity	NPC147091
0.8383	Intermediate Similarity	NPC31311
0.8314	Intermediate Similarity	NPC210918
0.8313	Intermediate Similarity	NPC210148
0.8313	Intermediate Similarity	NPC233029
0.8304	Intermediate Similarity	NPC276944
0.8304	Intermediate Similarity	NPC180306
0.8304	Intermediate Similarity	NPC238530
0.8304	Intermediate Similarity	NPC232514
0.8293	Intermediate Similarity	NPC475959
0.8286	Intermediate Similarity	NPC229166
0.8286	Intermediate Similarity	NPC199465
0.8286	Intermediate Similarity	NPC128560
0.8284	Intermediate Similarity	NPC111485
0.8258	Intermediate Similarity	NPC248642
0.8249	Intermediate Similarity	NPC99179
0.8249	Intermediate Similarity	NPC126284
0.8225	Intermediate Similarity	NPC129603
0.8222	Intermediate Similarity	NPC214116
0.8214	Intermediate Similarity	NPC41178
0.8214	Intermediate Similarity	NPC138487
0.8214	Intermediate Similarity	NPC216459
0.8212	Intermediate Similarity	NPC156576
0.8204	Intermediate Similarity	NPC223124
0.8204	Intermediate Similarity	NPC148898
0.8198	Intermediate Similarity	NPC302527
0.8198	Intermediate Similarity	NPC16805
0.8198	Intermediate Similarity	NPC167546
0.8192	Intermediate Similarity	NPC320223
0.8192	Intermediate Similarity	NPC114364
0.8176	Intermediate Similarity	NPC477080
0.8171	Intermediate Similarity	NPC149090
0.8171	Intermediate Similarity	NPC19520
0.8166	Intermediate Similarity	NPC146288
0.815	Intermediate Similarity	NPC24264
0.815	Intermediate Similarity	NPC476432
0.8103	Intermediate Similarity	NPC247389
0.8092	Intermediate Similarity	NPC225774
0.8092	Intermediate Similarity	NPC24465
0.8087	Intermediate Similarity	NPC63152
0.8084	Intermediate Similarity	NPC223125
0.8072	Intermediate Similarity	NPC59907
0.8072	Intermediate Similarity	NPC37144
0.807	Intermediate Similarity	NPC92191
0.807	Intermediate Similarity	NPC59028
0.8057	Intermediate Similarity	NPC204908
0.8057	Intermediate Similarity	NPC83198
0.8056	Intermediate Similarity	NPC116284
0.8046	Intermediate Similarity	NPC219341
0.8046	Intermediate Similarity	NPC264850
0.8046	Intermediate Similarity	NPC124657
0.8046	Intermediate Similarity	NPC13916
0.8043	Intermediate Similarity	NPC24260
0.8033	Intermediate Similarity	NPC82763
0.8023	Intermediate Similarity	NPC165797
0.8012	Intermediate Similarity	NPC65490
0.8012	Intermediate Similarity	NPC40389
0.8012	Intermediate Similarity	NPC148014
0.8012	Intermediate Similarity	NPC78359
0.8012	Intermediate Similarity	NPC315707
0.8	Intermediate Similarity	NPC155442
0.8	Intermediate Similarity	NPC312918
0.8	Intermediate Similarity	NPC476574
0.8	Intermediate Similarity	NPC304846
0.8	Intermediate Similarity	NPC298979
0.8	Intermediate Similarity	NPC477561
0.8	Intermediate Similarity	NPC150879
0.7989	Intermediate Similarity	NPC89199
0.7989	Intermediate Similarity	NPC54125
0.7989	Intermediate Similarity	NPC475754
0.7978	Intermediate Similarity	NPC476576
0.7978	Intermediate Similarity	NPC186546
0.7976	Intermediate Similarity	NPC274026
0.7964	Intermediate Similarity	NPC135538
0.7964	Intermediate Similarity	NPC428
0.7964	Intermediate Similarity	NPC246587
0.7964	Intermediate Similarity	NPC476571
0.7964	Intermediate Similarity	NPC24233
0.7964	Intermediate Similarity	NPC147390
0.7956	Intermediate Similarity	NPC73492
0.7956	Intermediate Similarity	NPC476575
0.7956	Intermediate Similarity	NPC299990
0.7953	Intermediate Similarity	NPC180756
0.7953	Intermediate Similarity	NPC323443
0.7946	Intermediate Similarity	NPC117717
0.7933	Intermediate Similarity	NPC283999
0.7923	Intermediate Similarity	NPC57036
0.7921	Intermediate Similarity	NPC232386
0.7921	Intermediate Similarity	NPC152680
0.7921	Intermediate Similarity	NPC190783
0.7919	Intermediate Similarity	NPC18402
0.7919	Intermediate Similarity	NPC232924
0.7919	Intermediate Similarity	NPC306902
0.7919	Intermediate Similarity	NPC477559
0.7919	Intermediate Similarity	NPC160298
0.7919	Intermediate Similarity	NPC266753
0.7917	Intermediate Similarity	NPC103379
0.7917	Intermediate Similarity	NPC477565
0.7912	Intermediate Similarity	NPC135772
0.791	Intermediate Similarity	NPC6152
0.7904	Intermediate Similarity	NPC191376
0.7904	Intermediate Similarity	NPC321505
0.7904	Intermediate Similarity	NPC476151
0.7904	Intermediate Similarity	NPC179825
0.7901	Intermediate Similarity	NPC474607
0.7895	Intermediate Similarity	NPC276588
0.7895	Intermediate Similarity	NPC54379
0.7895	Intermediate Similarity	NPC2413
0.7895	Intermediate Similarity	NPC110416
0.7895	Intermediate Similarity	NPC193949
0.7895	Intermediate Similarity	NPC189266
0.7895	Intermediate Similarity	NPC207757
0.7895	Intermediate Similarity	NPC184026
0.7895	Intermediate Similarity	NPC249797
0.7895	Intermediate Similarity	NPC5238
0.7895	Intermediate Similarity	NPC39701
0.7895	Intermediate Similarity	NPC93593
0.7895	Intermediate Similarity	NPC127674
0.7895	Intermediate Similarity	NPC469817
0.7895	Intermediate Similarity	NPC295691
0.7895	Intermediate Similarity	NPC278799
0.7895	Intermediate Similarity	NPC172765
0.7895	Intermediate Similarity	NPC204828
0.7892	Intermediate Similarity	NPC185838
0.7886	Intermediate Similarity	NPC231198
0.7886	Intermediate Similarity	NPC477563
0.7886	Intermediate Similarity	NPC196447
0.7886	Intermediate Similarity	NPC253043
0.7886	Intermediate Similarity	NPC78222
0.7886	Intermediate Similarity	NPC136508
0.7886	Intermediate Similarity	NPC306843
0.7886	Intermediate Similarity	NPC96603
0.7886	Intermediate Similarity	NPC212794
0.7886	Intermediate Similarity	NPC13504
0.7882	Intermediate Similarity	NPC133011
0.7882	Intermediate Similarity	NPC82285
0.7877	Intermediate Similarity	NPC329969
0.7877	Intermediate Similarity	NPC477558
0.787	Intermediate Similarity	NPC151895
0.787	Intermediate Similarity	NPC97221
0.787	Intermediate Similarity	NPC220858
0.787	Intermediate Similarity	NPC88249
0.787	Intermediate Similarity	NPC192768
0.7866	Intermediate Similarity	NPC188163
0.7866	Intermediate Similarity	NPC213206
0.7866	Intermediate Similarity	NPC328750
0.7866	Intermediate Similarity	NPC474915
0.7865	Intermediate Similarity	NPC239775
0.7861	Intermediate Similarity	NPC33256
0.7861	Intermediate Similarity	NPC69360
0.7857	Intermediate Similarity	NPC102760

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 NPC15919 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	196
0.1-0.2	657
0.2-0.3	978
0.3-0.4	2655
0.4-0.5	2573
0.5-0.6	1567
0.6-0.7	422
0.7-0.8	99
0.8-0.85	3
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.815	Intermediate Similarity	NPD3051	Approved
0.8103	Intermediate Similarity	NPD2969	Approved
0.8103	Intermediate Similarity	NPD2970	Approved
0.8046	Intermediate Similarity	NPD6071	Discontinued
0.8012	Intermediate Similarity	NPD2563	Approved
0.8012	Intermediate Similarity	NPD2560	Approved
0.7955	Intermediate Similarity	NPD2489	Approved
0.7955	Intermediate Similarity	NPD27	Approved
0.7941	Intermediate Similarity	NPD4772	Phase 2
0.7941	Intermediate Similarity	NPD4773	Phase 2
0.7901	Intermediate Similarity	NPD4577	Approved
0.7901	Intermediate Similarity	NPD4578	Approved
0.7869	Intermediate Similarity	NPD4663	Approved
0.7866	Intermediate Similarity	NPD4664	Clinical (unspecified phase)
0.7826	Intermediate Similarity	NPD7906	Approved
0.7802	Intermediate Similarity	NPD7311	Approved
0.7802	Intermediate Similarity	NPD7313	Approved
0.7802	Intermediate Similarity	NPD7310	Approved
0.7802	Intermediate Similarity	NPD7312	Approved
0.7798	Intermediate Similarity	NPD4584	Approved
0.776	Intermediate Similarity	NPD7309	Approved
0.7753	Intermediate Similarity	NPD4481	Phase 3
0.7725	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.7708	Intermediate Similarity	NPD5005	Approved
0.7708	Intermediate Similarity	NPD5006	Approved
0.7684	Intermediate Similarity	NPD4420	Approved
0.7663	Intermediate Similarity	NPD8053	Approved
0.7663	Intermediate Similarity	NPD8054	Approved
0.7624	Intermediate Similarity	NPD8156	Discontinued
0.7605	Intermediate Similarity	NPD4237	Approved
0.7605	Intermediate Similarity	NPD4236	Phase 3
0.7574	Intermediate Similarity	NPD6783	Clinical (unspecified phase)
0.7569	Intermediate Similarity	NPD8251	Approved
0.7569	Intermediate Similarity	NPD8099	Discontinued
0.7569	Intermediate Similarity	NPD8252	Approved
0.7543	Intermediate Similarity	NPD2977	Approved
0.7543	Intermediate Similarity	NPD6818	Clinical (unspecified phase)
0.7543	Intermediate Similarity	NPD2978	Approved
0.7513	Intermediate Similarity	NPD7296	Approved
0.7487	Intermediate Similarity	NPD5582	Discontinued
0.7459	Intermediate Similarity	NPD2898	Approved
0.7419	Intermediate Similarity	NPD7281	Phase 3
0.7419	Intermediate Similarity	NPD7280	Phase 3
0.7412	Intermediate Similarity	NPD5241	Discontinued
0.7389	Intermediate Similarity	NPD6107	Approved
0.7385	Intermediate Similarity	NPD3452	Approved
0.7385	Intermediate Similarity	NPD3450	Approved
0.738	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7379	Intermediate Similarity	NPD6997	Phase 2
0.736	Intermediate Similarity	NPD6788	Approved
0.7358	Intermediate Similarity	NPD2975	Approved
0.7358	Intermediate Similarity	NPD2973	Approved
0.7358	Intermediate Similarity	NPD2974	Approved
0.7348	Intermediate Similarity	NPD4010	Discontinued
0.7345	Intermediate Similarity	NPD5773	Approved
0.7345	Intermediate Similarity	NPD5772	Approved
0.7333	Intermediate Similarity	NPD4580	Approved
0.7318	Intermediate Similarity	NPD7831	Phase 2
0.7318	Intermediate Similarity	NPD7833	Phase 2
0.7318	Intermediate Similarity	NPD7832	Clinical (unspecified phase)
0.7314	Intermediate Similarity	NPD4017	Approved
0.731	Intermediate Similarity	NPD4002	Approved
0.731	Intermediate Similarity	NPD4004	Approved
0.7299	Intermediate Similarity	NPD3641	Approved
0.7299	Intermediate Similarity	NPD6031	Approved
0.7299	Intermediate Similarity	NPD6030	Approved
0.7299	Intermediate Similarity	NPD3639	Approved
0.7299	Intermediate Similarity	NPD3640	Phase 3
0.7296	Intermediate Similarity	NPD2494	Approved
0.7296	Intermediate Similarity	NPD2493	Approved
0.7288	Intermediate Similarity	NPD7298	Approved
0.7277	Intermediate Similarity	NPD2488	Approved
0.7277	Intermediate Similarity	NPD2490	Approved
0.7273	Intermediate Similarity	NPD4583	Approved
0.7273	Intermediate Similarity	NPD4582	Approved
0.7263	Intermediate Similarity	NPD7243	Clinical (unspecified phase)
0.7255	Intermediate Similarity	NPD7047	Phase 3
0.7238	Intermediate Similarity	NPD7201	Clinical (unspecified phase)
0.7234	Intermediate Similarity	NPD2968	Approved
0.7234	Intermediate Similarity	NPD2971	Approved
0.7222	Intermediate Similarity	NPD5604	Discontinued
0.7216	Intermediate Similarity	NPD4005	Discontinued
0.7209	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7194	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7192	Intermediate Similarity	NPD7827	Phase 1
0.7184	Intermediate Similarity	NPD1754	Clinical (unspecified phase)
0.7159	Intermediate Similarity	NPD4210	Discontinued
0.7152	Intermediate Similarity	NPD2669	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD5312	Approved
0.7151	Intermediate Similarity	NPD5313	Approved
0.7128	Intermediate Similarity	NPD7667	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD2238	Phase 2
0.71	Intermediate Similarity	NPD4040	Phase 1
0.7093	Intermediate Similarity	NPD5177	Phase 3
0.7086	Intermediate Similarity	NPD1424	Approved
0.7074	Intermediate Similarity	NPD7007	Discovery
0.7069	Intermediate Similarity	NPD7124	Phase 2
0.7065	Intermediate Similarity	NPD4166	Phase 2
0.7059	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7033	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7033	Intermediate Similarity	NPD4055	Discovery
0.7022	Intermediate Similarity	NPD7261	Clinical (unspecified phase)
0.7016	Intermediate Similarity	NPD6853	Approved
0.7016	Intermediate Similarity	NPD6851	Approved
0.701	Intermediate Similarity	NPD5525	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD4727	Phase 1
0.7	Intermediate Similarity	NPD3382	Approved
0.7	Intermediate Similarity	NPD3383	Approved
0.7	Intermediate Similarity	NPD3384	Approved
0.6995	Remote Similarity	NPD6841	Approved
0.6995	Remote Similarity	NPD6842	Approved
0.6995	Remote Similarity	NPD6843	Phase 3
0.6994	Remote Similarity	NPD4162	Approved
0.6994	Remote Similarity	NPD3060	Approved
0.6991	Remote Similarity	NPD6625	Approved
0.6989	Remote Similarity	NPD6365	Clinical (unspecified phase)
0.6984	Remote Similarity	NPD6297	Approved
0.6978	Remote Similarity	NPD4581	Clinical (unspecified phase)
0.6964	Remote Similarity	NPD554	Clinical (unspecified phase)
0.6935	Remote Similarity	NPD6687	Approved
0.6935	Remote Similarity	NPD6688	Approved
0.6932	Remote Similarity	NPD2421	Approved
0.6932	Remote Similarity	NPD2420	Approved
0.6923	Remote Similarity	NPD3808	Clinical (unspecified phase)
0.6915	Remote Similarity	NPD3057	Approved
0.6914	Remote Similarity	NPD5160	Discontinued
0.6914	Remote Similarity	NPD2677	Approved
0.6906	Remote Similarity	NPD7945	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD5718	Phase 2
0.6901	Remote Similarity	NPD6896	Approved
0.6901	Remote Similarity	NPD6895	Approved
0.6893	Remote Similarity	NPD7019	Approved
0.6893	Remote Similarity	NPD7020	Approved
0.6886	Remote Similarity	NPD5752	Clinical (unspecified phase)
0.6885	Remote Similarity	NPD4967	Phase 2
0.6885	Remote Similarity	NPD4966	Approved
0.6885	Remote Similarity	NPD4965	Approved
0.6881	Remote Similarity	NPD7497	Discontinued
0.6879	Remote Similarity	NPD1375	Discontinued
0.6875	Remote Similarity	NPD3534	Clinical (unspecified phase)
0.6871	Remote Similarity	NPD3705	Approved
0.6865	Remote Similarity	NPD5677	Discontinued
0.686	Remote Similarity	NPD1753	Discontinued
0.6859	Remote Similarity	NPD7149	Clinical (unspecified phase)
0.685	Remote Similarity	NPD8095	Phase 1
0.6842	Remote Similarity	NPD2492	Phase 1
0.6832	Remote Similarity	NPD2972	Approved
0.6832	Remote Similarity	NPD3533	Approved
0.6832	Remote Similarity	NPD3448	Approved
0.6824	Remote Similarity	NPD3110	Approved
0.6824	Remote Similarity	NPD3109	Approved
0.6821	Remote Similarity	NPD1632	Clinical (unspecified phase)
0.6816	Remote Similarity	NPD5976	Discontinued
0.6814	Remote Similarity	NPD7607	Clinical (unspecified phase)
0.6811	Remote Similarity	NPD6234	Discontinued
0.6802	Remote Similarity	NPD6111	Discontinued
0.68	Remote Similarity	NPD6674	Discontinued
0.6798	Remote Similarity	NPD4123	Phase 3
0.6796	Remote Similarity	NPD4678	Approved
0.6796	Remote Similarity	NPD4675	Approved
0.6786	Remote Similarity	NPD2843	Phase 2
0.6786	Remote Similarity	NPD2845	Phase 2
0.6782	Remote Similarity	NPD2029	Clinical (unspecified phase)
0.678	Remote Similarity	NPD3845	Phase 1
0.678	Remote Similarity	NPD2422	Clinical (unspecified phase)
0.6778	Remote Similarity	NPD3686	Approved
0.6778	Remote Similarity	NPD3687	Approved
0.6776	Remote Similarity	NPD5619	Clinical (unspecified phase)
0.6772	Remote Similarity	NPD5602	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD4474	Approved
0.6765	Remote Similarity	NPD4475	Approved
0.6763	Remote Similarity	NPD4108	Discontinued
0.676	Remote Similarity	NPD7527	Clinical (unspecified phase)
0.676	Remote Similarity	NPD7526	Approved
0.676	Remote Similarity	NPD52	Approved
0.6758	Remote Similarity	NPD6723	Discontinued
0.6758	Remote Similarity	NPD6072	Discontinued
0.6754	Remote Similarity	NPD3885	Approved
0.6749	Remote Similarity	NPD2491	Approved
0.6745	Remote Similarity	NPD4111	Phase 1
0.6742	Remote Similarity	NPD3124	Discontinued
0.6738	Remote Similarity	NPD7802	Discontinued
0.6738	Remote Similarity	NPD3984	Clinical (unspecified phase)
0.6738	Remote Similarity	NPD3983	Phase 3
0.6737	Remote Similarity	NPD7228	Approved
0.6736	Remote Similarity	NPD7549	Discontinued
0.6736	Remote Similarity	NPD8453	Clinical (unspecified phase)
0.6733	Remote Similarity	NPD4107	Approved
0.6724	Remote Similarity	NPD2161	Phase 2
0.6722	Remote Similarity	NPD2122	Discontinued
0.6721	Remote Similarity	NPD37	Approved
0.6718	Remote Similarity	NPD5087	Clinical (unspecified phase)
0.6716	Remote Similarity	NPD6877	Discontinued
0.6704	Remote Similarity	NPD4160	Clinical (unspecified phase)
0.6701	Remote Similarity	NPD7235	Clinical (unspecified phase)
0.6686	Remote Similarity	NPD3656	Approved
0.6685	Remote Similarity	NPD6666	Approved
0.6685	Remote Similarity	NPD6667	Approved
0.6685	Remote Similarity	NPD4585	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