NPASS Compound

Structure

NPC474364 OpenBabel07101718322D 22 23 0 0 1 0 0 0 0 0999 V2000 0.8090 4.5878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6551 -1.4122 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7891 -0.9122 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5211 -0.9122 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7891 0.0878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5211 0.0878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6180 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3090 -0.9511 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8090 1.5878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9230 1.5878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8090 3.5878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6551 0.5878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8090 0.5878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0570 2.0878 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 0.3090 -0.9511 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6551 1.5878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6750 3.0878 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.2788 -1.7601 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.5211 2.0878 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7891 2.0878 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0570 3.0878 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 11 1 0 0 0 0 2 3 2 0 0 0 0 2 4 1 0 0 0 0 3 5 1 0 0 0 0 4 6 2 0 0 0 0 5 12 2 0 0 0 0 6 12 1 0 0 0 0 7 8 2 0 0 0 0 7 13 1 0 0 0 0 8 15 1 0 0 0 0 9 13 2 0 0 0 0 9 14 1 0 0 0 0 10 14 1 0 0 0 0 10 20 1 0 0 0 0 11 17 2 0 0 0 0 11 21 1 0 0 0 0 12 16 1 0 0 0 0 13 22 1 0 0 0 0 14 21 1 0 0 0 0 15 18 2 0 0 0 0 15 22 1 0 0 0 0 16 19 2 0 0 0 0 16 20 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	302.08
Volume:	299.829
LogP:	2.731
LogD:	2.409
LogS:	-3.603
# Rotatable Bonds:	7
TPSA:	85.97
# H-Bond Aceptor:	6
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.675
Synthetic Accessibility Score:	2.791
Fsp3:	0.125
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:	-4.674
MDCK Permeability:	2.85352307400899e-05
Pgp-inhibitor:	0.009
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.026
20% Bioavailability (F20%):	0.921
30% Bioavailability (F30%):	0.074

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.533
Plasma Protein Binding (PPB):	93.85700225830078%
Volume Distribution (VD):	0.386
Pgp-substrate:	9.043827056884766%

ADMET: Metabolism

CYP1A2-inhibitor:	0.888
CYP1A2-substrate:	0.071
CYP2C19-inhibitor:	0.395
CYP2C19-substrate:	0.06
CYP2C9-inhibitor:	0.469
CYP2C9-substrate:	0.526
CYP2D6-inhibitor:	0.033
CYP2D6-substrate:	0.22
CYP3A4-inhibitor:	0.039
CYP3A4-substrate:	0.216

ADMET: Excretion

Clearance (CL):	7.121
Half-life (T1/2):	0.945

ADMET: Toxicity

hERG Blockers:	0.013
Human Hepatotoxicity (H-HT):	0.138
Drug-inuced Liver Injury (DILI):	0.852
AMES Toxicity:	0.726
Rat Oral Acute Toxicity:	0.626
Maximum Recommended Daily Dose:	0.093
Skin Sensitization:	0.882
Carcinogencity:	0.731
Eye Corrosion:	0.161
Eye Irritation:	0.92
Respiratory Toxicity:	0.104

Download Data

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

Natural Product: NPC474364

Natural Product ID:	NPC474364
*Common Name:**	Acetylmelodorinol
IUPAC Name:	[(3Z)-2-acetyloxy-3-(5-oxofuran-2-ylidene)propyl] benzoate
Synonyms:	Acetylmelodorinol
Standard InCHIKey:	GRILELGQNUBIAJ-LCYFTJDESA-N
Standard InCHI:	InChI=1S/C16H14O6/c1-11(17)21-14(9-13-7-8-15(18)22-13)10-20-16(19)12-5-3-2-4-6-12/h2-9,14H,10H2,1H3/b13-9-
SMILES:	CC(=O)OC(COC(=O)C1=CC=CC=C1)C=C2C=CC(=O)O2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL465644
PubChem CID:	5388650
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002279] Benzene and substituted derivatives [CHEMONTID:0000176] Benzoic acids and derivatives [CHEMONTID:0001350] Benzoic acid esters

*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
NPO6499	Melodorum fruticosum	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[1919592]
NPO6499	Melodorum fruticosum	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]

☑ 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	5
GI50	56

Activity Type	# Activity
Cell Line	61

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	ED50	=	2.89	ug ml-1	PMID[538980]
NPT83	Cell Line	MCF7	Homo sapiens	ED50	=	1.96	ug ml-1	PMID[538980]
NPT139	Cell Line	HT-29	Homo sapiens	ED50	=	2.38	ug ml-1	PMID[538980]
NPT373	Cell Line	SK-MEL-5	Homo sapiens	ED50	=	4.21	ug ml-1	PMID[538980]
NPT375	Cell Line	Malme-3M	Homo sapiens	ED50	=	2.74	ug ml-1	PMID[538980]
NPT368	Cell Line	SN12C	Homo sapiens	GI50	n.a.	31188.9	nM	PMID[538981]
NPT370	Cell Line	NCI-H23	Homo sapiens	GI50	n.a.	31188.9	nM	PMID[538981]
NPT369	Cell Line	ACHN	Homo sapiens	GI50	n.a.	31188.9	nM	PMID[538981]
NPT371	Cell Line	UO-31	Homo sapiens	GI50	n.a.	31188.9	nM	PMID[538981]
NPT116	Cell Line	HL-60	Homo sapiens	GI50	n.a.	31188.9	nM	PMID[538981]
NPT372	Cell Line	HOP-92	Homo sapiens	GI50	n.a.	31188.9	nM	PMID[538981]
NPT374	Cell Line	SF-539	Homo sapiens	GI50	n.a.	31188.9	nM	PMID[538981]
NPT373	Cell Line	SK-MEL-5	Homo sapiens	GI50	n.a.	31188.9	nM	PMID[538981]
NPT375	Cell Line	Malme-3M	Homo sapiens	GI50	n.a.	31188.9	nM	PMID[538981]
NPT111	Cell Line	K562	Homo sapiens	GI50	n.a.	10543.87	nM	PMID[538981]
NPT376	Cell Line	A498	Homo sapiens	GI50	n.a.	31188.9	nM	PMID[538981]
NPT377	Cell Line	OVCAR-3	Homo sapiens	GI50	n.a.	31188.9	nM	PMID[538981]
NPT379	Cell Line	HOP-62	Homo sapiens	GI50	n.a.	31188.9	nM	PMID[538981]
NPT380	Cell Line	U-251	Homo sapiens	GI50	n.a.	31188.9	nM	PMID[538981]
NPT381	Cell Line	OVCAR-8	Homo sapiens	GI50	n.a.	31188.9	nM	PMID[538981]
NPT382	Cell Line	OVCAR-5	Homo sapiens	GI50	n.a.	31188.9	nM	PMID[538981]
NPT572	Cell Line	DMS-273	Homo sapiens	GI50	n.a.	31188.9	nM	PMID[538981]
NPT383	Cell Line	SNB-19	Homo sapiens	GI50	n.a.	31188.9	nM	PMID[538981]
NPT384	Cell Line	TK-10	Homo sapiens	GI50	n.a.	31188.9	nM	PMID[538981]
NPT573	Cell Line	M19-MEL	Homo sapiens	GI50	n.a.	31188.9	nM	PMID[538981]
NPT323	Cell Line	SW-620	Homo sapiens	GI50	n.a.	31188.9	nM	PMID[538981]
NPT455	Cell Line	NCI-H522	Homo sapiens	GI50	n.a.	31188.9	nM	PMID[538981]
NPT386	Cell Line	KM12	Homo sapiens	GI50	n.a.	31188.9	nM	PMID[538981]
NPT387	Cell Line	M14	Homo sapiens	GI50	n.a.	31188.9	nM	PMID[538981]
NPT574	Cell Line	XF498	Homo sapiens	GI50	n.a.	31188.9	nM	PMID[538981]
NPT388	Cell Line	NCI-H322M	Homo sapiens	GI50	n.a.	31188.9	nM	PMID[538981]
NPT389	Cell Line	RPMI-8226	Homo sapiens	GI50	n.a.	31188.9	nM	PMID[538981]
NPT456	Cell Line	OVCAR-4	Homo sapiens	GI50	n.a.	31188.9	nM	PMID[538981]
NPT390	Cell Line	LOX IMVI	Homo sapiens	GI50	n.a.	31188.9	nM	PMID[538981]
NPT575	Cell Line	KM-20L2	Homo sapiens	GI50	n.a.	31188.9	nM	PMID[538981]
NPT81	Cell Line	A549	Homo sapiens	GI50	n.a.	31188.9	nM	PMID[538981]
NPT391	Cell Line	HCC 2998	Homo sapiens	GI50	n.a.	31188.9	nM	PMID[538981]
NPT392	Cell Line	SNB-75	Homo sapiens	GI50	n.a.	31188.9	nM	PMID[538981]
NPT395	Cell Line	SF-268	Homo sapiens	GI50	n.a.	31188.9	nM	PMID[538981]
NPT393	Cell Line	HCT-116	Homo sapiens	GI50	n.a.	31188.9	nM	PMID[538981]
NPT394	Cell Line	EKVX	Homo sapiens	GI50	n.a.	31188.9	nM	PMID[538981]
NPT731	Cell Line	LXFL 529	Homo sapiens	GI50	n.a.	31188.9	nM	PMID[538981]
NPT576	Cell Line	DMS-114	Homo sapiens	GI50	n.a.	31188.9	nM	PMID[538981]
NPT146	Cell Line	SK-OV-3	Homo sapiens	GI50	n.a.	31188.9	nM	PMID[538981]
NPT397	Cell Line	NCI-H460	Homo sapiens	GI50	n.a.	31188.9	nM	PMID[538981]
NPT398	Cell Line	UACC-62	Homo sapiens	GI50	n.a.	31188.9	nM	PMID[538981]
NPT308	Cell Line	CAKI-1	Homo sapiens	GI50	n.a.	31188.9	nM	PMID[538981]
NPT399	Cell Line	SF-295	Homo sapiens	GI50	n.a.	31188.9	nM	PMID[538981]
NPT577	Cell Line	RXF 631	Homo sapiens	GI50	n.a.	23988.33	nM	PMID[538981]
NPT458	Cell Line	IGROV-1	Homo sapiens	GI50	n.a.	31188.9	nM	PMID[538981]
NPT578	Cell Line	SNB-78	Homo sapiens	GI50	n.a.	31188.9	nM	PMID[538981]
NPT401	Cell Line	786-0	Homo sapiens	GI50	n.a.	31188.9	nM	PMID[538981]
NPT579	Cell Line	DLD-1	Homo sapiens	GI50	n.a.	31188.9	nM	PMID[538981]
NPT403	Cell Line	UACC-257	Homo sapiens	GI50	n.a.	31188.9	nM	PMID[538981]
NPT404	Cell Line	CCRF-CEM	Homo sapiens	GI50	n.a.	31188.9	nM	PMID[538981]
NPT405	Cell Line	NCI-H226	Homo sapiens	GI50	n.a.	31188.9	nM	PMID[538981]
NPT139	Cell Line	HT-29	Homo sapiens	GI50	n.a.	31188.9	nM	PMID[538981]
NPT170	Cell Line	SK-MEL-28	Homo sapiens	GI50	n.a.	31188.9	nM	PMID[538981]
NPT406	Cell Line	RXF 393	Homo sapiens	GI50	n.a.	31188.9	nM	PMID[538981]
NPT732	Cell Line	HOP-18	Homo sapiens	GI50	n.a.	31188.9	nM	PMID[538981]
NPT407	Cell Line	COLO 205	Homo sapiens	GI50	n.a.	31188.9	nM	PMID[538981]

☑ 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 NPC474364 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	221
0.1-0.2	1172
0.2-0.3	3439
0.3-0.4	8951
0.4-0.5	10557
0.5-0.6	11550
0.6-0.7	6024
0.7-0.8	676
0.8-0.85	63
0.85-0.9	36
0.9-0.95	5
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9333	High Similarity	NPC474314
0.9118	High Similarity	NPC474365
0.9118	High Similarity	NPC301943
0.9	High Similarity	NPC92754
0.9	High Similarity	NPC276775
0.9	High Similarity	NPC249912
0.8942	High Similarity	NPC269457
0.8911	High Similarity	NPC225060
0.8911	High Similarity	NPC78701
0.8911	High Similarity	NPC35448
0.8889	High Similarity	NPC161611
0.8868	High Similarity	NPC469636
0.8824	High Similarity	NPC146351
0.8824	High Similarity	NPC325497
0.8807	High Similarity	NPC308744
0.88	High Similarity	NPC130398
0.8738	High Similarity	NPC70624
0.8716	High Similarity	NPC474176
0.8704	High Similarity	NPC474157
0.8692	High Similarity	NPC265407
0.8692	High Similarity	NPC83628
0.8679	High Similarity	NPC30594
0.8679	High Similarity	NPC37622
0.8641	High Similarity	NPC118343
0.8641	High Similarity	NPC203925
0.8636	High Similarity	NPC307651
0.8636	High Similarity	NPC474363
0.8611	High Similarity	NPC174099
0.8585	High Similarity	NPC209632
0.8559	High Similarity	NPC210092
0.8558	High Similarity	NPC42211
0.8545	High Similarity	NPC272524
0.8532	High Similarity	NPC476003
0.8519	High Similarity	NPC17417
0.8519	High Similarity	NPC281604
0.8519	High Similarity	NPC10251
0.8505	High Similarity	NPC119271
0.8491	Intermediate Similarity	NPC269644
0.8491	Intermediate Similarity	NPC114594
0.8476	Intermediate Similarity	NPC188895
0.8455	Intermediate Similarity	NPC158282
0.844	Intermediate Similarity	NPC196246
0.844	Intermediate Similarity	NPC214067
0.844	Intermediate Similarity	NPC251854
0.844	Intermediate Similarity	NPC93084
0.8426	Intermediate Similarity	NPC56493
0.8396	Intermediate Similarity	NPC60679
0.8396	Intermediate Similarity	NPC89886
0.8393	Intermediate Similarity	NPC474685
0.839	Intermediate Similarity	NPC246166
0.8378	Intermediate Similarity	NPC128368
0.8364	Intermediate Similarity	NPC305912
0.8364	Intermediate Similarity	NPC1082
0.8349	Intermediate Similarity	NPC269023
0.8349	Intermediate Similarity	NPC99846
0.8333	Intermediate Similarity	NPC469574
0.8319	Intermediate Similarity	NPC149691
0.8318	Intermediate Similarity	NPC31786
0.8304	Intermediate Similarity	NPC477411
0.83	Intermediate Similarity	NPC173443
0.8288	Intermediate Similarity	NPC82899
0.8288	Intermediate Similarity	NPC270699
0.8269	Intermediate Similarity	NPC270654
0.8257	Intermediate Similarity	NPC156648
0.8224	Intermediate Similarity	NPC82426
0.8224	Intermediate Similarity	NPC234305
0.8224	Intermediate Similarity	NPC91820
0.8205	Intermediate Similarity	NPC50872
0.8198	Intermediate Similarity	NPC210089
0.8198	Intermediate Similarity	NPC260818
0.8158	Intermediate Similarity	NPC226093
0.8142	Intermediate Similarity	NPC153053
0.8131	Intermediate Similarity	NPC45613
0.8125	Intermediate Similarity	NPC321852
0.8103	Intermediate Similarity	NPC293424
0.81	Intermediate Similarity	NPC89377
0.802	Intermediate Similarity	NPC304760
0.8018	Intermediate Similarity	NPC85493
0.8017	Intermediate Similarity	NPC45104
0.8017	Intermediate Similarity	NPC217423
0.8	Intermediate Similarity	NPC318107
0.8	Intermediate Similarity	NPC216387
0.7982	Intermediate Similarity	NPC87069
0.7982	Intermediate Similarity	NPC85977
0.7981	Intermediate Similarity	NPC261181
0.7966	Intermediate Similarity	NPC473243
0.7961	Intermediate Similarity	NPC119631
0.7944	Intermediate Similarity	NPC472318
0.7944	Intermediate Similarity	NPC98911
0.7941	Intermediate Similarity	NPC220893
0.7934	Intermediate Similarity	NPC125053
0.7931	Intermediate Similarity	NPC190298
0.7917	Intermediate Similarity	NPC475692
0.7917	Intermediate Similarity	NPC474283
0.79	Intermediate Similarity	NPC58616
0.789	Intermediate Similarity	NPC160382
0.7886	Intermediate Similarity	NPC472707
0.7876	Intermediate Similarity	NPC243355
0.7876	Intermediate Similarity	NPC167504
0.7869	Intermediate Similarity	NPC476599
0.7857	Intermediate Similarity	NPC40178
0.7851	Intermediate Similarity	NPC475691
0.7845	Intermediate Similarity	NPC188907
0.7845	Intermediate Similarity	NPC220540
0.7845	Intermediate Similarity	NPC100353
0.784	Intermediate Similarity	NPC475478
0.7838	Intermediate Similarity	NPC474376
0.7838	Intermediate Similarity	NPC475203
0.7838	Intermediate Similarity	NPC472316
0.7838	Intermediate Similarity	NPC472315
0.7826	Intermediate Similarity	NPC196075
0.7815	Intermediate Similarity	NPC230951
0.7807	Intermediate Similarity	NPC79496
0.7797	Intermediate Similarity	NPC311091
0.7797	Intermediate Similarity	NPC471033
0.7797	Intermediate Similarity	NPC27633
0.7797	Intermediate Similarity	NPC94637
0.7797	Intermediate Similarity	NPC94298
0.7778	Intermediate Similarity	NPC128249
0.7778	Intermediate Similarity	NPC475569
0.7769	Intermediate Similarity	NPC472703
0.7768	Intermediate Similarity	NPC470391
0.7768	Intermediate Similarity	NPC47536
0.7768	Intermediate Similarity	NPC277788
0.776	Intermediate Similarity	NPC475508
0.7759	Intermediate Similarity	NPC81808
0.7757	Intermediate Similarity	NPC253423
0.775	Intermediate Similarity	NPC144547
0.7739	Intermediate Similarity	NPC17693
0.7736	Intermediate Similarity	NPC5472
0.7731	Intermediate Similarity	NPC90522
0.7731	Intermediate Similarity	NPC328459
0.7723	Intermediate Similarity	NPC294134
0.7714	Intermediate Similarity	NPC77273
0.7712	Intermediate Similarity	NPC240664
0.7705	Intermediate Similarity	NPC472704
0.7705	Intermediate Similarity	NPC471466
0.7698	Intermediate Similarity	NPC282230
0.7698	Intermediate Similarity	NPC183348
0.7692	Intermediate Similarity	NPC62765
0.7686	Intermediate Similarity	NPC26285
0.7685	Intermediate Similarity	NPC229242
0.7679	Intermediate Similarity	NPC51174
0.7679	Intermediate Similarity	NPC1065
0.7679	Intermediate Similarity	NPC136962
0.7674	Intermediate Similarity	NPC202729
0.7672	Intermediate Similarity	NPC53953
0.7672	Intermediate Similarity	NPC237366
0.7667	Intermediate Similarity	NPC988
0.7667	Intermediate Similarity	NPC243059
0.7667	Intermediate Similarity	NPC72977
0.7667	Intermediate Similarity	NPC289432
0.7667	Intermediate Similarity	NPC280827
0.7664	Intermediate Similarity	NPC61944
0.7661	Intermediate Similarity	NPC110211
0.7661	Intermediate Similarity	NPC204579
0.7661	Intermediate Similarity	NPC114096
0.7661	Intermediate Similarity	NPC472706
0.7658	Intermediate Similarity	NPC171831
0.7658	Intermediate Similarity	NPC242913
0.7658	Intermediate Similarity	NPC280616
0.7656	Intermediate Similarity	NPC38420
0.7656	Intermediate Similarity	NPC136608
0.7652	Intermediate Similarity	NPC23332
0.7652	Intermediate Similarity	NPC212415
0.7652	Intermediate Similarity	NPC54626
0.7652	Intermediate Similarity	NPC57879
0.7652	Intermediate Similarity	NPC185840
0.7642	Intermediate Similarity	NPC221798
0.7642	Intermediate Similarity	NPC295664
0.7642	Intermediate Similarity	NPC23453
0.7638	Intermediate Similarity	NPC470977
0.7638	Intermediate Similarity	NPC233860
0.7638	Intermediate Similarity	NPC196979
0.7638	Intermediate Similarity	NPC15083
0.7638	Intermediate Similarity	NPC470976
0.7638	Intermediate Similarity	NPC233692
0.7638	Intermediate Similarity	NPC239358
0.7636	Intermediate Similarity	NPC25458
0.7627	Intermediate Similarity	NPC470860
0.7627	Intermediate Similarity	NPC131192
0.7627	Intermediate Similarity	NPC128825
0.7623	Intermediate Similarity	NPC223351
0.7623	Intermediate Similarity	NPC69403
0.7623	Intermediate Similarity	NPC291189
0.7619	Intermediate Similarity	NPC66246
0.7619	Intermediate Similarity	NPC170546
0.7615	Intermediate Similarity	NPC217621
0.7615	Intermediate Similarity	NPC27721
0.7607	Intermediate Similarity	NPC228936
0.7607	Intermediate Similarity	NPC474408
0.7607	Intermediate Similarity	NPC470764
0.7607	Intermediate Similarity	NPC252004
0.7607	Intermediate Similarity	NPC306740
0.76	Intermediate Similarity	NPC148026
0.7597	Intermediate Similarity	NPC311339
0.7586	Intermediate Similarity	NPC13784
0.7583	Intermediate Similarity	NPC61779
0.7583	Intermediate Similarity	NPC204784
0.7581	Intermediate Similarity	NPC4164

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 NPC474364 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	198
0.1-0.2	827
0.2-0.3	1381
0.3-0.4	2750
0.4-0.5	2306
0.5-0.6	1250
0.6-0.7	392
0.7-0.8	40
0.8-0.85	4
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8704	High Similarity	NPD2181	Clinical (unspecified phase)
0.8641	High Similarity	NPD1238	Approved
0.8611	High Similarity	NPD2067	Discontinued
0.8519	High Similarity	NPD2182	Approved
0.8393	Intermediate Similarity	NPD690	Clinical (unspecified phase)
0.8318	Intermediate Similarity	NPD164	Approved
0.8	Intermediate Similarity	NPD9259	Approved
0.8	Intermediate Similarity	NPD9257	Approved
0.7981	Intermediate Similarity	NPD1202	Approved
0.7797	Intermediate Similarity	NPD9545	Approved
0.7768	Intermediate Similarity	NPD1358	Approved
0.7692	Intermediate Similarity	NPD9258	Approved
0.7692	Intermediate Similarity	NPD9256	Approved
0.7652	Intermediate Similarity	NPD1609	Clinical (unspecified phase)
0.7652	Intermediate Similarity	NPD969	Suspended
0.7627	Intermediate Similarity	NPD9493	Approved
0.7619	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7573	Intermediate Similarity	NPD1282	Approved
0.7541	Intermediate Similarity	NPD6287	Discontinued
0.754	Intermediate Similarity	NPD6832	Phase 2
0.7523	Intermediate Similarity	NPD9495	Approved
0.7522	Intermediate Similarity	NPD3134	Approved
0.7521	Intermediate Similarity	NPD1241	Discontinued
0.7521	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.752	Intermediate Similarity	NPD1019	Discontinued
0.75	Intermediate Similarity	NPD2199	Approved
0.75	Intermediate Similarity	NPD2198	Approved
0.748	Intermediate Similarity	NPD9717	Approved
0.7479	Intermediate Similarity	NPD694	Clinical (unspecified phase)
0.7411	Intermediate Similarity	NPD6647	Phase 2
0.7407	Intermediate Similarity	NPD9260	Approved
0.7391	Intermediate Similarity	NPD6831	Clinical (unspecified phase)
0.7385	Intermediate Similarity	NPD1933	Approved
0.7381	Intermediate Similarity	NPD6007	Clinical (unspecified phase)
0.7345	Intermediate Similarity	NPD1237	Approved
0.7345	Intermediate Similarity	NPD5909	Discontinued
0.7311	Intermediate Similarity	NPD2629	Approved
0.7273	Intermediate Similarity	NPD2347	Approved
0.7258	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7257	Intermediate Similarity	NPD9261	Approved
0.7252	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7206	Intermediate Similarity	NPD4628	Phase 3
0.7182	Intermediate Similarity	NPD1989	Approved
0.7165	Intermediate Similarity	NPD1203	Approved
0.7153	Intermediate Similarity	NPD3887	Approved
0.7143	Intermediate Similarity	NPD2567	Approved
0.7143	Intermediate Similarity	NPD2569	Approved
0.7143	Intermediate Similarity	NPD7798	Approved
0.7129	Intermediate Similarity	NPD9490	Approved
0.7121	Intermediate Similarity	NPD447	Suspended
0.7105	Intermediate Similarity	NPD1931	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD1929	Approved
0.7105	Intermediate Similarity	NPD1930	Approved
0.7087	Intermediate Similarity	NPD1876	Approved
0.7087	Intermediate Similarity	NPD5667	Approved
0.7077	Intermediate Similarity	NPD7008	Discontinued
0.7073	Intermediate Similarity	NPD1894	Discontinued
0.7063	Intermediate Similarity	NPD3972	Approved
0.7045	Intermediate Similarity	NPD4307	Phase 2
0.7037	Intermediate Similarity	NPD3672	Approved
0.7037	Intermediate Similarity	NPD3673	Approved
0.7031	Intermediate Similarity	NPD9567	Approved
0.7031	Intermediate Similarity	NPD552	Approved
0.7031	Intermediate Similarity	NPD553	Approved
0.7023	Intermediate Similarity	NPD2313	Discontinued
0.7023	Intermediate Similarity	NPD6798	Discontinued
0.7023	Intermediate Similarity	NPD3764	Approved
0.7019	Intermediate Similarity	NPD9491	Approved
0.7009	Intermediate Similarity	NPD9267	Approved
0.7009	Intermediate Similarity	NPD9264	Approved
0.7009	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7009	Intermediate Similarity	NPD9263	Approved
0.7	Intermediate Similarity	NPD5277	Phase 2
0.6992	Remote Similarity	NPD230	Phase 1
0.6992	Remote Similarity	NPD6355	Discontinued
0.6991	Remote Similarity	NPD2066	Phase 3
0.6985	Remote Similarity	NPD2355	Clinical (unspecified phase)
0.6985	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6985	Remote Similarity	NPD2353	Approved
0.6984	Remote Similarity	NPD518	Clinical (unspecified phase)
0.6983	Remote Similarity	NPD9697	Approved
0.6977	Remote Similarity	NPD5647	Approved
0.697	Remote Similarity	NPD6233	Phase 2
0.697	Remote Similarity	NPD4062	Phase 3
0.6967	Remote Similarity	NPD4198	Discontinued
0.6949	Remote Similarity	NPD74	Approved
0.6949	Remote Similarity	NPD9266	Approved
0.6929	Remote Similarity	NPD6799	Approved
0.6923	Remote Similarity	NPD9494	Approved
0.6916	Remote Similarity	NPD1087	Approved
0.6899	Remote Similarity	NPD3267	Approved
0.6899	Remote Similarity	NPD3266	Approved
0.6894	Remote Similarity	NPD411	Approved
0.6891	Remote Similarity	NPD4233	Approved
0.6891	Remote Similarity	NPD4234	Approved
0.6885	Remote Similarity	NPD5951	Approved
0.6884	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.688	Remote Similarity	NPD5585	Approved
0.6879	Remote Similarity	NPD5401	Approved
0.6863	Remote Similarity	NPD227	Approved
0.6863	Remote Similarity	NPD225	Approved
0.6861	Remote Similarity	NPD7702	Clinical (unspecified phase)
0.6855	Remote Similarity	NPD5536	Phase 2
0.6847	Remote Similarity	NPD5122	Clinical (unspecified phase)
0.6846	Remote Similarity	NPD2788	Approved
0.6846	Remote Similarity	NPD2798	Approved
0.6838	Remote Similarity	NPD4308	Phase 3
0.6838	Remote Similarity	NPD2799	Discontinued
0.6825	Remote Similarity	NPD5305	Approved
0.6825	Remote Similarity	NPD5306	Approved
0.6825	Remote Similarity	NPD17	Approved
0.6818	Remote Similarity	NPD6039	Approved
0.6815	Remote Similarity	NPD1654	Clinical (unspecified phase)
0.6815	Remote Similarity	NPD3528	Clinical (unspecified phase)
0.6791	Remote Similarity	NPD3142	Approved
0.6791	Remote Similarity	NPD3373	Approved
0.6791	Remote Similarity	NPD3140	Approved
0.6789	Remote Similarity	NPD689	Discontinued
0.6789	Remote Similarity	NPD800	Approved
0.6788	Remote Similarity	NPD1551	Phase 2
0.6788	Remote Similarity	NPD2438	Suspended
0.6788	Remote Similarity	NPD2935	Discontinued
0.6786	Remote Similarity	NPD2354	Approved
0.6786	Remote Similarity	NPD1693	Approved
0.6783	Remote Similarity	NPD5403	Approved
0.6777	Remote Similarity	NPD9508	Approved
0.6772	Remote Similarity	NPD4106	Approved
0.6772	Remote Similarity	NPD4136	Approved
0.6772	Remote Similarity	NPD4135	Approved
0.6772	Remote Similarity	NPD3496	Discontinued
0.6769	Remote Similarity	NPD2797	Approved
0.6769	Remote Similarity	NPD2160	Approved
0.6769	Remote Similarity	NPD2627	Approved
0.6769	Remote Similarity	NPD2159	Approved
0.6769	Remote Similarity	NPD2626	Approved
0.6769	Remote Similarity	NPD2625	Approved
0.6769	Remote Similarity	NPD2628	Approved
0.6754	Remote Similarity	NPD5926	Approved
0.6748	Remote Similarity	NPD9281	Approved
0.6746	Remote Similarity	NPD5691	Approved
0.6739	Remote Similarity	NPD2346	Discontinued
0.6738	Remote Similarity	NPD7236	Approved
0.6727	Remote Similarity	NPD1090	Approved
0.6727	Remote Similarity	NPD1086	Approved
0.6727	Remote Similarity	NPD1089	Approved
0.6724	Remote Similarity	NPD1932	Approved
0.6723	Remote Similarity	NPD290	Approved
0.6721	Remote Similarity	NPD5535	Approved
0.6719	Remote Similarity	NPD4807	Approved
0.6719	Remote Similarity	NPD4806	Approved
0.6719	Remote Similarity	NPD1281	Approved
0.6718	Remote Similarity	NPD6085	Phase 2
0.6718	Remote Similarity	NPD5740	Clinical (unspecified phase)
0.6716	Remote Similarity	NPD7713	Phase 3
0.6715	Remote Similarity	NPD3748	Approved
0.6714	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6713	Remote Similarity	NPD6273	Approved
0.6694	Remote Similarity	NPD4141	Clinical (unspecified phase)
0.6693	Remote Similarity	NPD1778	Approved
0.6691	Remote Similarity	NPD6653	Approved
0.669	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.669	Remote Similarity	NPD3455	Phase 2
0.6667	Remote Similarity	NPD3663	Approved
0.6667	Remote Similarity	NPD3661	Approved
0.6667	Remote Similarity	NPD1608	Approved
0.6667	Remote Similarity	NPD2796	Approved
0.6667	Remote Similarity	NPD5204	Approved
0.6667	Remote Similarity	NPD3662	Phase 3
0.6667	Remote Similarity	NPD2240	Approved
0.6667	Remote Similarity	NPD2239	Approved
0.6667	Remote Similarity	NPD226	Approved
0.6667	Remote Similarity	NPD2684	Approved
0.6667	Remote Similarity	NPD1481	Phase 2
0.6667	Remote Similarity	NPD2979	Phase 3
0.6667	Remote Similarity	NPD5738	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD3664	Approved
0.6667	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6644	Remote Similarity	NPD6599	Discontinued
0.6642	Remote Similarity	NPD3268	Approved
0.6642	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6642	Remote Similarity	NPD2670	Approved
0.6641	Remote Similarity	NPD7457	Clinical (unspecified phase)
0.6641	Remote Similarity	NPD6362	Approved
0.6641	Remote Similarity	NPD3847	Discontinued
0.6622	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6621	Remote Similarity	NPD957	Approved
0.662	Remote Similarity	NPD7440	Discontinued
0.6615	Remote Similarity	NPD4359	Approved
0.6614	Remote Similarity	NPD4105	Approved
0.6614	Remote Similarity	NPD4102	Approved
0.6612	Remote Similarity	NPD5239	Approved
0.6612	Remote Similarity	NPD5237	Approved
0.6612	Remote Similarity	NPD5235	Approved
0.6612	Remote Similarity	NPD5240	Approved
0.6612	Remote Similarity	NPD5236	Approved
0.6607	Remote Similarity	NPD1088	Approved
0.6599	Remote Similarity	NPD6386	Approved
0.6599	Remote Similarity	NPD6385	Approved
0.6597	Remote Similarity	NPD2186	Approved
0.6597	Remote Similarity	NPD5049	Phase 3

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