NPASS Compound

Structure

CID244554 OpenBabel06191716042D 24 28 0 0 1 0 0 0 0 0999 V2000 1.8256 -0.7296 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4747 -1.5484 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2568 1.3221 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6202 1.7852 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9248 0.4981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6829 1.6754 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2091 -0.2911 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5137 0.7494 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5444 0.7493 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3924 0.7492 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.4849 0.2862 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4849 1.2123 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8808 1.2123 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3420 0.6990 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.1118 1.5838 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6829 -0.1769 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8808 0.2862 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2088 1.7899 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.1119 -0.0850 0.0000 N 0 0 3 0 0 0 0 0 0 0 0 0 4.6542 2.2641 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6821 0.1734 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6829 -1.0913 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.4985 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 21 1 0 0 0 0 2 22 1 0 0 0 0 3 4 2 0 0 0 0 3 10 1 0 0 0 0 5 10 1 0 0 0 0 5 14 1 0 0 0 0 6 12 2 0 0 0 0 6 13 1 0 0 0 0 7 11 1 0 0 0 0 7 19 1 0 0 0 0 8 15 1 0 0 0 0 8 19 1 0 0 0 0 9 23 1 0 0 0 0 9 24 1 0 0 0 0 10 21 1 1 0 0 0 11 12 1 0 0 0 0 11 16 2 0 0 0 0 12 18 1 0 0 0 0 13 17 2 0 0 0 0 13 23 1 0 0 0 0 14 18 1 6 0 0 0 14 19 1 0 0 0 0 15 18 1 1 0 0 0 15 20 1 0 0 0 0 16 17 1 0 0 0 0 16 22 1 0 0 0 0 17 24 1 0 0 0 0 18 4 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	331.14
Volume:	321.504
LogP:	1.036
LogD:	0.838
LogS:	-2.773
# Rotatable Bonds:	2
TPSA:	60.39
# H-Bond Aceptor:	6
# H-Bond Donor:	1
# Rings:	5
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.822
Synthetic Accessibility Score:	5.339
Fsp3:	0.556
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:	-4.935
MDCK Permeability:	1.9666320440592244e-05
Pgp-inhibitor:	0.025
Pgp-substrate:	0.935
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.011
30% Bioavailability (F30%):	0.005

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.984
Plasma Protein Binding (PPB):	24.54802703857422%
Volume Distribution (VD):	1.822
Pgp-substrate:	58.13218307495117%

ADMET: Metabolism

CYP1A2-inhibitor:	0.094
CYP1A2-substrate:	0.835
CYP2C19-inhibitor:	0.062
CYP2C19-substrate:	0.851
CYP2C9-inhibitor:	0.027
CYP2C9-substrate:	0.607
CYP2D6-inhibitor:	0.229
CYP2D6-substrate:	0.598
CYP3A4-inhibitor:	0.904
CYP3A4-substrate:	0.842

ADMET: Excretion

Clearance (CL):	4.819
Half-life (T1/2):	0.694

ADMET: Toxicity

hERG Blockers:	0.338
Human Hepatotoxicity (H-HT):	0.669
Drug-inuced Liver Injury (DILI):	0.079
AMES Toxicity:	0.669
Rat Oral Acute Toxicity:	0.906
Maximum Recommended Daily Dose:	0.98
Skin Sensitization:	0.27
Carcinogencity:	0.094
Eye Corrosion:	0.003
Eye Irritation:	0.013
Respiratory Toxicity:	0.918

Download Data

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

Natural Product: NPC244554

Natural Product ID:	NPC244554
*Common Name:**	Ambelline
IUPAC Name:	n.a.
Synonyms:	Ambelline
Standard InCHIKey:	QAHZAHIPKNLGAS-KZRPXEQKSA-N
Standard InCHI:	InChI=1S/C18H21NO5/c1-21-10-3-4-18-12-6-13-17(24-9-23-13)16(22-2)11(12)7-19(8-15(18)20)14(18)5-10/h3-4,6,10,14-15,20H,5,7-9H2,1-2H3/t10-,14+,15-,18+/m0/s1
SMILES:	CO[C@H]1C=C[C@@]23[C@@H](C1)N(Cc1c3cc3OCOc3c1OC)C[C@@H]2O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1173110
PubChem CID:	25092366
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
NPO13176	Garcinia densivenia	Species	Clusiaceae	Eukaryota	n.a.	stem	n.a.	DOI[10.1016/S0031-9422(00)83950-3]
NPO23239	Amaryllis belladonna	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1021/ja01076a047]
NPO11841	Psorothamnus arborescens	Species	Fabaceae	Eukaryota	root	n.a.	n.a.	PMID[16441066]
NPO11841	Psorothamnus arborescens	Species	Fabaceae	Eukaryota	n.a.	root	n.a.	PMID[16441066]
NPO24293	Neorautanenia mitis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16562843]
NPO4617	Tanacetum cinerariifolium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24253739]
NPO23239	Amaryllis belladonna	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[6512532]
NPO11658	Alternanthera philoxeroides	Species	Amaranthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO23239	Amaryllis belladonna	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO4617	Tanacetum cinerariifolium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11658	Alternanthera philoxeroides	Species	Amaranthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28746	Cynoglossum zeylanicum	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5896	Crinum laurentii	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24293	Neorautanenia mitis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23239	Amaryllis belladonna	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23239	Amaryllis belladonna	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO30375	Crinum laurentll	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO11658	Alternanthera philoxeroides	Species	Amaranthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13176	Garcinia densivenia	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13027	Eucalyptus torelliana	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23091	Halocarpus bidwillii	Species	Podocarpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28746	Cynoglossum zeylanicum	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2381	Phacelocarpus peperocarpos	Species	Phacelocarpaceae	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]
NPO27248	Artemisia pygmaea	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5896	Crinum laurentii	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11841	Psorothamnus arborescens	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11265	Coryphantha cornifera	Species	Cactaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12363	Dermocybe sanguinea	Species	Cortinariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4617	Tanacetum cinerariifolium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10281	Fritillaria roylei	Species	Liliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24293	Neorautanenia mitis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4020	Dorstenia turbinata	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23239	Amaryllis belladonna	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13772	Didemnum proliferum	Species	Didemnidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5924	Brunsvigia josephinae	Species	Amaryllidaceae	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
ED50	1
IC50	6
Others	2

Activity Type	# Activity
Cell Line	4
Individual Protein	2
NON-MOLECULAR	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT168	Cell Line	P388	Mus musculus	ED50	=	1.6	ug ml-1	PMID[490873]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	10000.0	nM	PMID[490874]
NPT916	Cell Line	SK-MEL	Homo sapiens	IC50	>	10000.0	nM	PMID[490874]
NPT169	Cell Line	B16-F10	Mus musculus	IC50	>	10000.0	nM	PMID[490874]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	86000.0	nM	PMID[490874]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	10000.0	nM	PMID[490874]
NPT72	Individual Protein	Solute carrier organic anion transporter family member 1B3	Homo sapiens	Inhibition	=	88.47	%	PMID[490875]
NPT73	Individual Protein	Solute carrier organic anion transporter family member 1B1	Homo sapiens	Inhibition	=	91.95	%	PMID[490875]

☑ 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 NPC244554 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	308
0.1-0.2	1324
0.2-0.3	4536
0.3-0.4	12163
0.4-0.5	6821
0.5-0.6	12519
0.6-0.7	4055
0.7-0.8	772
0.8-0.85	116
0.85-0.9	64
0.9-0.95	13
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
0.963	High Similarity	NPC75958
0.9568	High Similarity	NPC82533
0.9568	High Similarity	NPC266176
0.9568	High Similarity	NPC158148
0.9568	High Similarity	NPC290759
0.9451	High Similarity	NPC470739
0.9451	High Similarity	NPC477640
0.9451	High Similarity	NPC225597
0.9448	High Similarity	NPC58766
0.9448	High Similarity	NPC475686
0.939	High Similarity	NPC474475
0.9281	High Similarity	NPC474470
0.9181	High Similarity	NPC9867
0.908	High Similarity	NPC215829
0.908	High Similarity	NPC97072
0.9042	High Similarity	NPC311991
0.9036	High Similarity	NPC100566
0.9	High Similarity	NPC15919
0.897	High Similarity	NPC218614
0.897	High Similarity	NPC320104
0.8951	High Similarity	NPC78733
0.8935	High Similarity	NPC2314
0.8922	High Similarity	NPC181653
0.8922	High Similarity	NPC190332
0.8922	High Similarity	NPC252960
0.8916	High Similarity	NPC247972
0.8876	High Similarity	NPC65403
0.88	High Similarity	NPC214116
0.8779	High Similarity	NPC118633
0.8779	High Similarity	NPC294790
0.8779	High Similarity	NPC148693
0.8772	High Similarity	NPC187678
0.8772	High Similarity	NPC304675
0.8721	High Similarity	NPC237044
0.869	High Similarity	NPC180306
0.8671	High Similarity	NPC474325
0.8639	High Similarity	NPC476002
0.8621	High Similarity	NPC474745
0.8588	High Similarity	NPC57812
0.8588	High Similarity	NPC474324
0.858	High Similarity	NPC59907
0.858	High Similarity	NPC37144
0.858	High Similarity	NPC475981
0.858	High Similarity	NPC474746
0.8563	High Similarity	NPC59028
0.8563	High Similarity	NPC92191
0.8554	High Similarity	NPC147091
0.8547	High Similarity	NPC63152
0.8538	High Similarity	NPC475845
0.8523	High Similarity	NPC248642
0.8514	High Similarity	NPC126284
0.85	High Similarity	NPC117717
0.8488	Intermediate Similarity	NPC474708
0.8485	Intermediate Similarity	NPC148898
0.8475	Intermediate Similarity	NPC156576
0.8448	Intermediate Similarity	NPC49353
0.8443	Intermediate Similarity	NPC234392
0.8443	Intermediate Similarity	NPC31311
0.8439	Intermediate Similarity	NPC149090
0.8439	Intermediate Similarity	NPC19520
0.8421	Intermediate Similarity	NPC264850
0.8421	Intermediate Similarity	NPC13916
0.8418	Intermediate Similarity	NPC275132
0.8402	Intermediate Similarity	NPC249274
0.8402	Intermediate Similarity	NPC4304
0.8402	Intermediate Similarity	NPC205167
0.8383	Intermediate Similarity	NPC41178
0.8383	Intermediate Similarity	NPC216459
0.8383	Intermediate Similarity	NPC138487
0.838	Intermediate Similarity	NPC230098
0.8363	Intermediate Similarity	NPC24465
0.8363	Intermediate Similarity	NPC276944
0.8363	Intermediate Similarity	NPC232514
0.8363	Intermediate Similarity	NPC238530
0.8354	Intermediate Similarity	NPC475959
0.8333	Intermediate Similarity	NPC146288
0.8324	Intermediate Similarity	NPC204908
0.8324	Intermediate Similarity	NPC83198
0.8315	Intermediate Similarity	NPC233718
0.8315	Intermediate Similarity	NPC299990
0.8315	Intermediate Similarity	NPC73492
0.8305	Intermediate Similarity	NPC99179
0.8297	Intermediate Similarity	NPC24260
0.8284	Intermediate Similarity	NPC148014
0.8284	Intermediate Similarity	NPC315707
0.8284	Intermediate Similarity	NPC40389
0.8284	Intermediate Similarity	NPC129603
0.8284	Intermediate Similarity	NPC65490
0.8284	Intermediate Similarity	NPC78359
0.8266	Intermediate Similarity	NPC150879
0.8266	Intermediate Similarity	NPC210918
0.8263	Intermediate Similarity	NPC210148
0.8263	Intermediate Similarity	NPC223124
0.8263	Intermediate Similarity	NPC233029
0.8253	Intermediate Similarity	NPC274026
0.8235	Intermediate Similarity	NPC328700
0.8235	Intermediate Similarity	NPC119818
0.8235	Intermediate Similarity	NPC2173
0.8235	Intermediate Similarity	NPC202771
0.8208	Intermediate Similarity	NPC24264
0.8208	Intermediate Similarity	NPC476432
0.8192	Intermediate Similarity	NPC283999
0.8187	Intermediate Similarity	NPC82763
0.8182	Intermediate Similarity	NPC190783
0.8182	Intermediate Similarity	NPC232386
0.8182	Intermediate Similarity	NPC152680
0.8177	Intermediate Similarity	NPC57036
0.8161	Intermediate Similarity	NPC247389
0.8156	Intermediate Similarity	NPC32413
0.8156	Intermediate Similarity	NPC474506
0.815	Intermediate Similarity	NPC231198
0.815	Intermediate Similarity	NPC167546
0.815	Intermediate Similarity	NPC225774
0.815	Intermediate Similarity	NPC16805
0.815	Intermediate Similarity	NPC302527
0.8146	Intermediate Similarity	NPC114364
0.8146	Intermediate Similarity	NPC23219
0.8146	Intermediate Similarity	NPC320223
0.8144	Intermediate Similarity	NPC223125
0.8136	Intermediate Similarity	NPC128560
0.8136	Intermediate Similarity	NPC199465
0.8136	Intermediate Similarity	NPC229166
0.8132	Intermediate Similarity	NPC476576
0.8132	Intermediate Similarity	NPC186546
0.8129	Intermediate Similarity	NPC111485
0.8118	Intermediate Similarity	NPC323443
0.8118	Intermediate Similarity	NPC180756
0.8114	Intermediate Similarity	NPC182257
0.8111	Intermediate Similarity	NPC102760
0.8111	Intermediate Similarity	NPC476575
0.8103	Intermediate Similarity	NPC124657
0.8103	Intermediate Similarity	NPC219341
0.8101	Intermediate Similarity	NPC470879
0.8101	Intermediate Similarity	NPC258695
0.8092	Intermediate Similarity	NPC233650
0.809	Intermediate Similarity	NPC112575
0.8087	Intermediate Similarity	NPC281581
0.8081	Intermediate Similarity	NPC18402
0.8079	Intermediate Similarity	NPC228040
0.8072	Intermediate Similarity	NPC476151
0.8061	Intermediate Similarity	NPC130926
0.8059	Intermediate Similarity	NPC93593
0.8057	Intermediate Similarity	NPC298979
0.8047	Intermediate Similarity	NPC82285
0.8047	Intermediate Similarity	NPC133011
0.8046	Intermediate Similarity	NPC134858
0.8043	Intermediate Similarity	NPC473716
0.8043	Intermediate Similarity	NPC475597
0.8032	Intermediate Similarity	NPC475654
0.8023	Intermediate Similarity	NPC239775
0.8023	Intermediate Similarity	NPC477080
0.8021	Intermediate Similarity	NPC73020
0.8021	Intermediate Similarity	NPC124302
0.8021	Intermediate Similarity	NPC70290
0.8021	Intermediate Similarity	NPC14622
0.8021	Intermediate Similarity	NPC46744
0.8021	Intermediate Similarity	NPC215098
0.801	Intermediate Similarity	NPC80472
0.8	Intermediate Similarity	NPC267408
0.7989	Intermediate Similarity	NPC293871
0.7989	Intermediate Similarity	NPC124433
0.7989	Intermediate Similarity	NPC59567
0.7977	Intermediate Similarity	NPC165797
0.7977	Intermediate Similarity	NPC232924
0.7977	Intermediate Similarity	NPC477559
0.7977	Intermediate Similarity	NPC160298
0.7977	Intermediate Similarity	NPC266753
0.7977	Intermediate Similarity	NPC306902
0.7976	Intermediate Similarity	NPC103379
0.7976	Intermediate Similarity	NPC477565
0.7966	Intermediate Similarity	NPC329911
0.7966	Intermediate Similarity	NPC118274
0.7966	Intermediate Similarity	NPC168753
0.7964	Intermediate Similarity	NPC476144
0.7964	Intermediate Similarity	NPC51957
0.7964	Intermediate Similarity	NPC210437
0.7964	Intermediate Similarity	NPC106295
0.7964	Intermediate Similarity	NPC16107
0.7955	Intermediate Similarity	NPC210140
0.7953	Intermediate Similarity	NPC193949
0.7953	Intermediate Similarity	NPC278799
0.7953	Intermediate Similarity	NPC2413
0.7953	Intermediate Similarity	NPC127674
0.7953	Intermediate Similarity	NPC54379
0.7953	Intermediate Similarity	NPC207757
0.7953	Intermediate Similarity	NPC204828
0.7953	Intermediate Similarity	NPC249797
0.7953	Intermediate Similarity	NPC189266
0.7953	Intermediate Similarity	NPC5238
0.7953	Intermediate Similarity	NPC39701
0.7953	Intermediate Similarity	NPC469817
0.7953	Intermediate Similarity	NPC172765
0.7953	Intermediate Similarity	NPC276588
0.7953	Intermediate Similarity	NPC110416
0.7953	Intermediate Similarity	NPC295691
0.7953	Intermediate Similarity	NPC184026
0.7952	Intermediate Similarity	NPC185838
0.7937	Intermediate Similarity	NPC72788
0.7937	Intermediate Similarity	NPC226652
0.7937	Intermediate Similarity	NPC314100

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 NPC244554 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	182
0.1-0.2	631
0.2-0.3	1030
0.3-0.4	2496
0.4-0.5	2534
0.5-0.6	1601
0.6-0.7	553
0.7-0.8	118
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
0.8314	Intermediate Similarity	NPD6071	Discontinued
0.8284	Intermediate Similarity	NPD2563	Approved
0.8284	Intermediate Similarity	NPD2560	Approved
0.8235	Intermediate Similarity	NPD5006	Approved
0.8235	Intermediate Similarity	NPD5005	Approved
0.8057	Intermediate Similarity	NPD2970	Approved
0.8057	Intermediate Similarity	NPD2969	Approved
0.8021	Intermediate Similarity	NPD4420	Approved
0.8	Intermediate Similarity	NPD3051	Approved
0.7978	Intermediate Similarity	NPD8156	Discontinued
0.7964	Intermediate Similarity	NPD4584	Approved
0.7927	Intermediate Similarity	NPD4664	Clinical (unspecified phase)
0.7921	Intermediate Similarity	NPD8251	Approved
0.7921	Intermediate Similarity	NPD8099	Discontinued
0.7921	Intermediate Similarity	NPD8252	Approved
0.7912	Intermediate Similarity	NPD8053	Approved
0.7912	Intermediate Similarity	NPD8054	Approved
0.791	Intermediate Similarity	NPD27	Approved
0.791	Intermediate Similarity	NPD2489	Approved
0.7895	Intermediate Similarity	NPD4772	Phase 2
0.7895	Intermediate Similarity	NPD4773	Phase 2
0.788	Intermediate Similarity	NPD7906	Approved
0.7826	Intermediate Similarity	NPD4663	Approved
0.7816	Intermediate Similarity	NPD6788	Approved
0.7809	Intermediate Similarity	NPD4481	Phase 3
0.7803	Intermediate Similarity	NPD6818	Clinical (unspecified phase)
0.7784	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.7771	Intermediate Similarity	NPD4236	Phase 3
0.7771	Intermediate Similarity	NPD4237	Approved
0.776	Intermediate Similarity	NPD4578	Approved
0.776	Intermediate Similarity	NPD4577	Approved
0.7709	Intermediate Similarity	NPD2898	Approved
0.7701	Intermediate Similarity	NPD2978	Approved
0.7701	Intermediate Similarity	NPD2977	Approved
0.7679	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7679	Intermediate Similarity	NPD5241	Discontinued
0.7663	Intermediate Similarity	NPD7310	Approved
0.7663	Intermediate Similarity	NPD7312	Approved
0.7663	Intermediate Similarity	NPD7313	Approved
0.7663	Intermediate Similarity	NPD7311	Approved
0.7647	Intermediate Similarity	NPD1424	Approved
0.7633	Intermediate Similarity	NPD6783	Clinical (unspecified phase)
0.7632	Intermediate Similarity	NPD5582	Discontinued
0.7622	Intermediate Similarity	NPD7309	Approved
0.7572	Intermediate Similarity	NPD4005	Discontinued
0.7571	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD5773	Approved
0.75	Intermediate Similarity	NPD2973	Approved
0.75	Intermediate Similarity	NPD2975	Approved
0.75	Intermediate Similarity	NPD2974	Approved
0.75	Intermediate Similarity	NPD5772	Approved
0.7486	Intermediate Similarity	NPD7201	Clinical (unspecified phase)
0.7473	Intermediate Similarity	NPD7280	Phase 3
0.7473	Intermediate Similarity	NPD7281	Phase 3
0.7472	Intermediate Similarity	NPD4055	Discovery
0.7444	Intermediate Similarity	NPD6107	Approved
0.7442	Intermediate Similarity	NPD1754	Clinical (unspecified phase)
0.7433	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7427	Intermediate Similarity	NPD7124	Phase 2
0.7414	Intermediate Similarity	NPD4210	Discontinued
0.7385	Intermediate Similarity	NPD4580	Approved
0.7382	Intermediate Similarity	NPD7296	Approved
0.7371	Intermediate Similarity	NPD4017	Approved
0.7371	Intermediate Similarity	NPD7261	Clinical (unspecified phase)
0.7358	Intermediate Similarity	NPD7667	Clinical (unspecified phase)
0.7356	Intermediate Similarity	NPD3640	Phase 3
0.7356	Intermediate Similarity	NPD3639	Approved
0.7356	Intermediate Similarity	NPD3641	Approved
0.7353	Intermediate Similarity	NPD5177	Phase 3
0.7347	Intermediate Similarity	NPD3450	Approved
0.7347	Intermediate Similarity	NPD2494	Approved
0.7347	Intermediate Similarity	NPD2493	Approved
0.7347	Intermediate Similarity	NPD3452	Approved
0.7333	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7327	Intermediate Similarity	NPD7827	Phase 1
0.7316	Intermediate Similarity	NPD7243	Clinical (unspecified phase)
0.7293	Intermediate Similarity	NPD5677	Discontinued
0.7278	Intermediate Similarity	NPD7833	Phase 2
0.7278	Intermediate Similarity	NPD7831	Phase 2
0.7278	Intermediate Similarity	NPD7832	Clinical (unspecified phase)
0.7262	Intermediate Similarity	NPD2200	Suspended
0.7257	Intermediate Similarity	NPD6031	Approved
0.7257	Intermediate Similarity	NPD6030	Approved
0.7251	Intermediate Similarity	NPD3060	Approved
0.7247	Intermediate Similarity	NPD7298	Approved
0.7236	Intermediate Similarity	NPD4583	Approved
0.7236	Intermediate Similarity	NPD4582	Approved
0.7232	Intermediate Similarity	NPD4678	Approved
0.7232	Intermediate Similarity	NPD4675	Approved
0.7225	Intermediate Similarity	NPD6842	Approved
0.7225	Intermediate Similarity	NPD6843	Phase 3
0.7225	Intermediate Similarity	NPD6841	Approved
0.7219	Intermediate Similarity	NPD6297	Approved
0.7213	Intermediate Similarity	NPD4010	Discontinued
0.7212	Intermediate Similarity	NPD2669	Clinical (unspecified phase)
0.7196	Intermediate Similarity	NPD2971	Approved
0.7196	Intermediate Similarity	NPD2968	Approved
0.7186	Intermediate Similarity	NPD2238	Phase 2
0.7186	Intermediate Similarity	NPD4002	Approved
0.7186	Intermediate Similarity	NPD4004	Approved
0.7182	Intermediate Similarity	NPD5604	Discontinued
0.7177	Intermediate Similarity	NPD6997	Phase 2
0.716	Intermediate Similarity	NPD6111	Discontinued
0.7158	Intermediate Similarity	NPD6851	Approved
0.7158	Intermediate Similarity	NPD6853	Approved
0.7157	Intermediate Similarity	NPD8095	Phase 1
0.7151	Intermediate Similarity	NPD3383	Approved
0.7151	Intermediate Similarity	NPD3382	Approved
0.7151	Intermediate Similarity	NPD3384	Approved
0.715	Intermediate Similarity	NPD2490	Approved
0.715	Intermediate Similarity	NPD2488	Approved
0.7136	Intermediate Similarity	NPD7047	Phase 3
0.7127	Intermediate Similarity	NPD4581	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD554	Clinical (unspecified phase)
0.712	Intermediate Similarity	NPD4166	Phase 2
0.7118	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7118	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7116	Intermediate Similarity	NPD6625	Approved
0.7112	Intermediate Similarity	NPD5312	Approved
0.7112	Intermediate Similarity	NPD5313	Approved
0.7111	Intermediate Similarity	NPD4585	Approved
0.7095	Intermediate Similarity	NPD5089	Approved
0.7095	Intermediate Similarity	NPD5090	Approved
0.7086	Intermediate Similarity	NPD7212	Phase 2
0.7086	Intermediate Similarity	NPD7213	Phase 3
0.7069	Intermediate Similarity	NPD2677	Approved
0.7062	Intermediate Similarity	NPD5976	Discontinued
0.7062	Intermediate Similarity	NPD3808	Clinical (unspecified phase)
0.7053	Intermediate Similarity	NPD7549	Discontinued
0.7053	Intermediate Similarity	NPD8453	Clinical (unspecified phase)
0.7052	Intermediate Similarity	NPD4162	Approved
0.7045	Intermediate Similarity	NPD7447	Phase 1
0.7035	Intermediate Similarity	NPD1375	Discontinued
0.7033	Intermediate Similarity	NPD4967	Phase 2
0.7033	Intermediate Similarity	NPD4965	Approved
0.7033	Intermediate Similarity	NPD4966	Approved
0.7022	Intermediate Similarity	NPD3686	Approved
0.7022	Intermediate Similarity	NPD3687	Approved
0.7018	Intermediate Similarity	NPD1753	Discontinued
0.7011	Intermediate Similarity	NPD7466	Approved
0.7	Intermediate Similarity	NPD6072	Discontinued
0.6994	Remote Similarity	NPD1372	Clinical (unspecified phase)
0.6989	Remote Similarity	NPD5297	Approved
0.6989	Remote Similarity	NPD5242	Approved
0.6989	Remote Similarity	NPD6688	Approved
0.6989	Remote Similarity	NPD6687	Approved
0.6974	Remote Similarity	NPD5525	Clinical (unspecified phase)
0.6971	Remote Similarity	NPD3692	Discontinued
0.6966	Remote Similarity	NPD4727	Phase 1
0.6965	Remote Similarity	NPD3057	Approved
0.6964	Remote Similarity	NPD5718	Phase 2
0.6963	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6961	Remote Similarity	NPD37	Approved
0.6959	Remote Similarity	NPD6896	Approved
0.6959	Remote Similarity	NPD6895	Approved
0.6952	Remote Similarity	NPD6365	Clinical (unspecified phase)
0.6949	Remote Similarity	NPD3158	Phase 1
0.6949	Remote Similarity	NPD4123	Phase 3
0.6949	Remote Similarity	NPD3157	Approved
0.6927	Remote Similarity	NPD3534	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD7235	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD2042	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD2041	Clinical (unspecified phase)
0.6911	Remote Similarity	NPD7149	Clinical (unspecified phase)
0.691	Remote Similarity	NPD7526	Approved
0.691	Remote Similarity	NPD52	Approved
0.691	Remote Similarity	NPD7527	Clinical (unspecified phase)
0.6901	Remote Similarity	NPD2492	Phase 1
0.6893	Remote Similarity	NPD2421	Approved
0.6893	Remote Similarity	NPD3124	Discontinued
0.6893	Remote Similarity	NPD1774	Approved
0.6893	Remote Similarity	NPD2420	Approved
0.6887	Remote Similarity	NPD7907	Approved
0.6882	Remote Similarity	NPD7199	Phase 2
0.6881	Remote Similarity	NPD3533	Approved
0.6881	Remote Similarity	NPD2972	Approved
0.6875	Remote Similarity	NPD5160	Discontinued
0.6872	Remote Similarity	NPD4111	Phase 1
0.6872	Remote Similarity	NPD4665	Approved
0.6868	Remote Similarity	NPD7945	Clinical (unspecified phase)
0.6866	Remote Similarity	NPD4107	Approved
0.6865	Remote Similarity	NPD5709	Phase 3
0.6865	Remote Similarity	NPD7400	Phase 3
0.6865	Remote Similarity	NPD6234	Discontinued
0.686	Remote Similarity	NPD5676	Approved
0.6859	Remote Similarity	NPD7007	Discovery
0.6859	Remote Similarity	NPD6996	Clinical (unspecified phase)
0.6854	Remote Similarity	NPD7020	Approved
0.6854	Remote Similarity	NPD7019	Approved
0.6845	Remote Similarity	NPD5752	Clinical (unspecified phase)
0.6836	Remote Similarity	NPD3122	Phase 3
0.6831	Remote Similarity	NPD7046	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD3705	Approved
0.6828	Remote Similarity	NPD2904	Discontinued
0.6828	Remote Similarity	NPD4666	Phase 3
0.6825	Remote Similarity	NPD5602	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD4474	Approved
0.6824	Remote Similarity	NPD4475	Approved
0.6822	Remote Similarity	NPD5619	Clinical (unspecified phase)
0.6816	Remote Similarity	NPD6090	Discontinued

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