NPASS Compound

Structure

CID16357 OpenBabel06191715342D 46 52 0 0 1 0 0 0 0 0999 V2000 2.4185 -4.2224 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2816 -1.3885 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4737 -1.6188 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4185 1.7776 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6169 1.8881 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9277 1.4439 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6587 -2.6652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3846 -3.1290 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6149 -3.2951 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1987 -2.8875 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2846 -1.7224 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2703 0.5362 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2846 -2.7224 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7754 0.0208 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9574 -2.9201 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1412 -3.9079 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1507 -3.3218 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1676 -1.5171 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4185 -0.2224 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3422 0.8477 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6865 -1.2224 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1936 -2.2383 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5595 -3.7356 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4185 -1.2224 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5714 0.3564 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5525 -1.7224 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4908 -3.4706 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8569 -3.8154 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5525 -2.7224 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.8828 -0.8541 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.0951 -3.6535 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7513 -3.1930 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5525 0.2776 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6865 -0.2224 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8021 0.8949 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3777 -0.3387 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4913 0.4507 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7205 -0.0406 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4185 -3.2224 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -2.5816 -0.6743 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -2.2495 -4.6416 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5669 -2.6144 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5525 1.2776 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3793 1.8011 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.5049 0.5377 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 39 1 0 0 0 0 2 40 1 0 0 0 0 3 42 1 0 0 0 0 4 43 1 0 0 0 0 5 44 1 0 0 0 0 6 45 1 0 0 0 0 7 9 2 0 0 0 0 7 22 1 0 0 0 0 8 10 2 0 0 0 0 8 23 1 0 0 0 0 9 31 1 0 0 0 0 10 32 1 0 0 0 0 11 13 1 0 0 0 0 11 24 1 0 0 0 0 12 14 1 0 0 0 0 12 25 1 0 0 0 0 13 39 1 0 0 0 0 14 40 1 0 0 0 0 15 22 2 0 0 0 0 15 27 1 0 0 0 0 16 23 2 0 0 0 0 16 28 1 0 0 0 0 17 23 1 0 0 0 0 18 22 1 0 0 0 0 19 24 2 0 0 0 0 19 33 1 0 0 0 0 20 25 2 0 0 0 0 20 35 1 0 0 0 0 21 26 2 0 0 0 0 21 34 1 0 0 0 0 24 26 1 0 0 0 0 25 36 1 0 0 0 0 26 29 1 0 0 0 0 27 28 1 0 0 0 0 27 31 2 0 0 0 0 28 32 2 0 0 0 0 29 17 1 6 0 0 0 29 39 1 0 0 0 0 30 18 1 6 0 0 0 30 36 1 0 0 0 0 30 40 1 0 0 0 0 31 41 1 0 0 0 0 32 42 1 0 0 0 0 33 34 2 0 0 0 0 33 43 1 0 0 0 0 34 46 1 0 0 0 0 35 37 2 0 0 0 0 35 44 1 0 0 0 0 36 38 2 0 0 0 0 37 38 1 0 0 0 0 37 45 1 0 0 0 0 38 46 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	622.3
Volume:	649.006
LogP:	6.21
LogD:	4.042
LogS:	-5.333
# Rotatable Bonds:	4
TPSA:	72.86
# H-Bond Aceptor:	8
# H-Bond Donor:	1
# Rings:	7
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.268
Synthetic Accessibility Score:	5.65
Fsp3:	0.368
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.732
MDCK Permeability:	2.549878081481438e-05
Pgp-inhibitor:	0.998
Pgp-substrate:	0.943
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.682
30% Bioavailability (F30%):	0.957

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.13
Plasma Protein Binding (PPB):	68.95204162597656%
Volume Distribution (VD):	1.383
Pgp-substrate:	17.399810791015625%

ADMET: Metabolism

CYP1A2-inhibitor:	0.055
CYP1A2-substrate:	0.973
CYP2C19-inhibitor:	0.075
CYP2C19-substrate:	0.97
CYP2C9-inhibitor:	0.039
CYP2C9-substrate:	0.631
CYP2D6-inhibitor:	0.014
CYP2D6-substrate:	0.964
CYP3A4-inhibitor:	0.116
CYP3A4-substrate:	0.955

ADMET: Excretion

Clearance (CL):	9.755
Half-life (T1/2):	0.231

ADMET: Toxicity

hERG Blockers:	0.965
Human Hepatotoxicity (H-HT):	0.079
Drug-inuced Liver Injury (DILI):	0.653
AMES Toxicity:	0.094
Rat Oral Acute Toxicity:	0.366
Maximum Recommended Daily Dose:	0.993
Skin Sensitization:	0.62
Carcinogencity:	0.027
Eye Corrosion:	0.003
Eye Irritation:	0.004
Respiratory Toxicity:	0.474

Download Data

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

Natural Product: NPC16357

Natural Product ID:	NPC16357
*Common Name:**	Funiferine
IUPAC Name:	n.a.
Synonyms:	NSC-189487
Standard InCHIKey:	ODCYIKWOTVSPKB-IHLOFXLRSA-N
Standard InCHI:	InChI=1S/C38H42N2O6/c1-39-13-11-24-19-33(43-4)34-21-26(24)29(39)17-23-8-10-32(42-3)28(16-23)27-15-22(7-9-31(27)41)18-30-36-25(12-14-40(30)2)20-35(44-5)37(45-6)38(36)46-34/h7-10,15-16,19-21,29-30,41H,11-14,17-18H2,1-6H3/t29-,30+/m1/s1
SMILES:	CN1CCc2cc(c3cc2[C@H]1Cc1ccc(c(-c2cc(ccc2O)C[C@H]2c4c(CCN2C)cc(c(c4O3)OC)OC)c1)OC)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2063764
PubChem CID:	70692876
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0000254] Ethers [CHEMONTID:0002463] Diarylethers

*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
NPO3595	Euscaphis japonica	Species	Staphyleaceae	Eukaryota	n.a.	twig	n.a.	DOI[10.1021/np1003593]
NPO3595	Euscaphis japonica	Species	Staphyleaceae	Eukaryota	Twigs	Yangming mountain, Taiwan	2008-APR	PMID[20873721]
NPO25727	Tabernaemontana divaricata	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23944995]
NPO25727	Tabernaemontana divaricata	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26231157]
NPO25727	Tabernaemontana divaricata	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[30169038]
NPO3595	Euscaphis japonica	Species	Staphyleaceae	Eukaryota	n.a.	pericarp	n.a.	PMID[4421158]
NPO3595	Euscaphis japonica	Species	Staphyleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO3595	Euscaphis japonica	Species	Staphyleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25727	Tabernaemontana divaricata	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5150	Mephitis mephitis	Species	Mephitidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6090	Caulerpa prolifera	Species	Caulerpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3436	Taraxacum linearisquameum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3595	Euscaphis japonica	Species	Staphyleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1514	Myxine glutinosa	Species	Myxinidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25727	Tabernaemontana divaricata	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8126	Ustilago virens	Species	Ustilaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16279	Croptilon divaricatum	Species	Asteraceae	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
IC50	2
Others	3

Activity Type	# Activity
Cell Line	4
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT466	Cell Line	U-937	Homo sapiens	MED	=	12.0	uM	PMID[558278]
NPT466	Cell Line	U-937	Homo sapiens	FC	=	2.5	n.a.	PMID[558278]
NPT466	Cell Line	U-937	Homo sapiens	IC50	>	50000.0	nM	PMID[558278]
NPT466	Cell Line	U-937	Homo sapiens	Activity	=	94.0	%	PMID[558278]
NPT992	Organism	Entamoeba histolytica	Entamoeba histolytica	IC50	=	28.3	ug.mL-1	PMID[558279]

☑ 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 NPC16357 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	368
0.1-0.2	1639
0.2-0.3	7869
0.3-0.4	10411
0.4-0.5	5045
0.5-0.6	8094
0.6-0.7	7439
0.7-0.8	1464
0.8-0.85	190
0.85-0.9	91
0.9-0.95	75
0.95-1	12

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC302245
1.0	High Similarity	NPC95426
0.994	High Similarity	NPC139783
0.994	High Similarity	NPC65312
0.9881	High Similarity	NPC22115
0.9881	High Similarity	NPC275680
0.9651	High Similarity	NPC256124
0.9643	High Similarity	NPC290582
0.9643	High Similarity	NPC54654
0.9643	High Similarity	NPC181796
0.9643	High Similarity	NPC222661
0.9643	High Similarity	NPC279228
0.9643	High Similarity	NPC311973
0.9643	High Similarity	NPC8836
0.9643	High Similarity	NPC258657
0.9643	High Similarity	NPC7715
0.9643	High Similarity	NPC229373
0.9643	High Similarity	NPC251735
0.9643	High Similarity	NPC182052
0.9643	High Similarity	NPC239824
0.9643	High Similarity	NPC290005
0.9643	High Similarity	NPC285931
0.9643	High Similarity	NPC223690
0.9643	High Similarity	NPC49075
0.9643	High Similarity	NPC217748
0.9643	High Similarity	NPC90998
0.9643	High Similarity	NPC104196
0.9643	High Similarity	NPC42663
0.9643	High Similarity	NPC328155
0.9643	High Similarity	NPC185639
0.9643	High Similarity	NPC15414
0.9643	High Similarity	NPC271013
0.9591	High Similarity	NPC206900
0.9588	High Similarity	NPC116465
0.9588	High Similarity	NPC212237
0.9586	High Similarity	NPC167116
0.9586	High Similarity	NPC274716
0.9586	High Similarity	NPC254441
0.9583	High Similarity	NPC286119
0.9527	High Similarity	NPC30779
0.948	High Similarity	NPC478093
0.9458	High Similarity	NPC276890
0.9458	High Similarity	NPC317439
0.9458	High Similarity	NPC115284
0.9458	High Similarity	NPC198498
0.9458	High Similarity	NPC317145
0.9458	High Similarity	NPC227060
0.9458	High Similarity	NPC63646
0.9458	High Similarity	NPC76682
0.9458	High Similarity	NPC10908
0.9425	High Similarity	NPC478091
0.9425	High Similarity	NPC478092
0.9425	High Similarity	NPC30182
0.9425	High Similarity	NPC473589
0.9405	High Similarity	NPC293093
0.9401	High Similarity	NPC12424
0.9401	High Similarity	NPC41376
0.9401	High Similarity	NPC251580
0.9401	High Similarity	NPC129518
0.9364	High Similarity	NPC175890
0.9364	High Similarity	NPC11296
0.9364	High Similarity	NPC274661
0.9364	High Similarity	NPC82457
0.9364	High Similarity	NPC48490
0.931	High Similarity	NPC60295
0.931	High Similarity	NPC191132
0.9257	High Similarity	NPC24260
0.9244	High Similarity	NPC302275
0.9222	High Similarity	NPC254581
0.9181	High Similarity	NPC475479
0.9181	High Similarity	NPC243454
0.9138	High Similarity	NPC47077
0.9138	High Similarity	NPC14507
0.9128	High Similarity	NPC239584
0.9075	High Similarity	NPC299990
0.9075	High Similarity	NPC73492
0.8989	High Similarity	NPC85381
0.8988	High Similarity	NPC268503
0.8988	High Similarity	NPC264850
0.8988	High Similarity	NPC250846
0.8988	High Similarity	NPC42549
0.8988	High Similarity	NPC317272
0.8988	High Similarity	NPC13916
0.8988	High Similarity	NPC256012
0.8988	High Similarity	NPC240841
0.8983	High Similarity	NPC318805
0.8983	High Similarity	NPC41122
0.895	High Similarity	NPC475654
0.8929	High Similarity	NPC24465
0.8889	High Similarity	NPC234318
0.8882	High Similarity	NPC204908
0.8882	High Similarity	NPC83198
0.8864	High Similarity	NPC249996
0.8837	High Similarity	NPC232386
0.8837	High Similarity	NPC190783
0.8837	High Similarity	NPC152680
0.882	High Similarity	NPC281581
0.881	High Similarity	NPC79402
0.881	High Similarity	NPC80759
0.88	High Similarity	NPC230276
0.88	High Similarity	NPC195538
0.88	High Similarity	NPC257269
0.8795	High Similarity	NPC247639
0.8795	High Similarity	NPC25084
0.8779	High Similarity	NPC239775
0.8771	High Similarity	NPC475597
0.8771	High Similarity	NPC473716
0.875	High Similarity	NPC119649
0.875	High Similarity	NPC230956
0.875	High Similarity	NPC205255
0.875	High Similarity	NPC235143
0.875	High Similarity	NPC476202
0.875	High Similarity	NPC271388
0.8743	High Similarity	NPC40496
0.8743	High Similarity	NPC119068
0.8721	High Similarity	NPC168753
0.8721	High Similarity	NPC118274
0.8691	High Similarity	NPC38964
0.869	High Similarity	NPC221864
0.8671	High Similarity	NPC475215
0.8671	High Similarity	NPC108434
0.8605	High Similarity	NPC474931
0.8605	High Similarity	NPC117188
0.8605	High Similarity	NPC205421
0.8605	High Similarity	NPC158376
0.8605	High Similarity	NPC12053
0.8605	High Similarity	NPC81218
0.8605	High Similarity	NPC145832
0.8605	High Similarity	NPC306555
0.8601	High Similarity	NPC82056
0.8588	High Similarity	NPC60186
0.8563	High Similarity	NPC10871
0.8538	High Similarity	NPC475393
0.8531	High Similarity	NPC474507
0.8523	High Similarity	NPC241704
0.8512	High Similarity	NPC276588
0.8512	High Similarity	NPC2413
0.8512	High Similarity	NPC278799
0.8512	High Similarity	NPC204828
0.8512	High Similarity	NPC127674
0.8512	High Similarity	NPC469817
0.8512	High Similarity	NPC249797
0.8512	High Similarity	NPC123323
0.8512	High Similarity	NPC54379
0.8512	High Similarity	NPC207757
0.8512	High Similarity	NPC39701
0.8512	High Similarity	NPC172765
0.8512	High Similarity	NPC184026
0.8512	High Similarity	NPC189266
0.8512	High Similarity	NPC295691
0.8512	High Similarity	NPC5238
0.8512	High Similarity	NPC193949
0.8512	High Similarity	NPC110416
0.8488	Intermediate Similarity	NPC13504
0.8488	Intermediate Similarity	NPC253043
0.8488	Intermediate Similarity	NPC136508
0.8488	Intermediate Similarity	NPC196447
0.8488	Intermediate Similarity	NPC96603
0.8488	Intermediate Similarity	NPC306843
0.8488	Intermediate Similarity	NPC477563
0.8488	Intermediate Similarity	NPC78222
0.8488	Intermediate Similarity	NPC212794
0.8439	Intermediate Similarity	NPC193853
0.8439	Intermediate Similarity	NPC223077
0.8439	Intermediate Similarity	NPC56887
0.843	Intermediate Similarity	NPC324144
0.843	Intermediate Similarity	NPC1229
0.8427	Intermediate Similarity	NPC32154
0.8418	Intermediate Similarity	NPC173416
0.8418	Intermediate Similarity	NPC148709
0.8418	Intermediate Similarity	NPC476577
0.8412	Intermediate Similarity	NPC476572
0.8382	Intermediate Similarity	NPC209377
0.8382	Intermediate Similarity	NPC169743
0.8315	Intermediate Similarity	NPC476565
0.8314	Intermediate Similarity	NPC27410
0.8314	Intermediate Similarity	NPC166014
0.8313	Intermediate Similarity	NPC51957
0.8313	Intermediate Similarity	NPC106295
0.8313	Intermediate Similarity	NPC16107
0.8313	Intermediate Similarity	NPC210437
0.8313	Intermediate Similarity	NPC476144
0.8313	Intermediate Similarity	NPC476151
0.8305	Intermediate Similarity	NPC477020
0.8305	Intermediate Similarity	NPC66341
0.8305	Intermediate Similarity	NPC192135
0.8297	Intermediate Similarity	NPC57036
0.8294	Intermediate Similarity	NPC99659
0.8294	Intermediate Similarity	NPC325871
0.8286	Intermediate Similarity	NPC204947
0.8274	Intermediate Similarity	NPC220858
0.8274	Intermediate Similarity	NPC88249
0.8274	Intermediate Similarity	NPC97221
0.8274	Intermediate Similarity	NPC192768
0.8274	Intermediate Similarity	NPC151895
0.8268	Intermediate Similarity	NPC320223
0.8268	Intermediate Similarity	NPC114364
0.8263	Intermediate Similarity	NPC7467
0.8261	Intermediate Similarity	NPC259350
0.8261	Intermediate Similarity	NPC223236

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 NPC16357 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	213
0.1-0.2	769
0.2-0.3	1116
0.3-0.4	2189
0.4-0.5	2371
0.5-0.6	1576
0.6-0.7	731
0.7-0.8	168
0.8-0.85	10
0.85-0.9	1
0.9-0.95	6
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9643	High Similarity	NPD8053	Approved
0.9643	High Similarity	NPD8054	Approved
0.9458	High Similarity	NPD8252	Approved
0.9458	High Similarity	NPD8099	Discontinued
0.9458	High Similarity	NPD8251	Approved
0.9401	High Similarity	NPD8156	Discontinued
0.8743	High Similarity	NPD8453	Clinical (unspecified phase)
0.8486	Intermediate Similarity	NPD8095	Phase 1
0.8313	Intermediate Similarity	NPD4584	Approved
0.8256	Intermediate Similarity	NPD6788	Approved
0.8098	Intermediate Similarity	NPD7906	Approved
0.8035	Intermediate Similarity	NPD6818	Clinical (unspecified phase)
0.8023	Intermediate Similarity	NPD4772	Phase 2
0.8023	Intermediate Similarity	NPD4773	Phase 2
0.8	Intermediate Similarity	NPD7832	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD7833	Phase 2
0.8	Intermediate Similarity	NPD7831	Phase 2
0.7952	Intermediate Similarity	NPD4664	Clinical (unspecified phase)
0.7937	Intermediate Similarity	NPD7667	Clinical (unspecified phase)
0.7921	Intermediate Similarity	NPD6071	Discontinued
0.788	Intermediate Similarity	NPD7312	Approved
0.788	Intermediate Similarity	NPD7313	Approved
0.788	Intermediate Similarity	NPD7310	Approved
0.788	Intermediate Similarity	NPD7311	Approved
0.7874	Intermediate Similarity	NPD7298	Approved
0.7838	Intermediate Similarity	NPD7309	Approved
0.7821	Intermediate Similarity	NPD3051	Approved
0.7803	Intermediate Similarity	NPD7261	Clinical (unspecified phase)
0.7784	Intermediate Similarity	NPD4577	Approved
0.7784	Intermediate Similarity	NPD4578	Approved
0.7778	Intermediate Similarity	NPD7447	Phase 1
0.7778	Intermediate Similarity	NPD2970	Approved
0.7778	Intermediate Similarity	NPD2969	Approved
0.7754	Intermediate Similarity	NPD4663	Approved
0.7735	Intermediate Similarity	NPD27	Approved
0.7735	Intermediate Similarity	NPD2489	Approved
0.773	Intermediate Similarity	NPD7549	Discontinued
0.7709	Intermediate Similarity	NPD7201	Clinical (unspecified phase)
0.7684	Intermediate Similarity	NPD2560	Approved
0.7684	Intermediate Similarity	NPD2563	Approved
0.7616	Intermediate Similarity	NPD2420	Approved
0.7616	Intermediate Similarity	NPD7213	Phase 3
0.7616	Intermediate Similarity	NPD7212	Phase 2
0.7616	Intermediate Similarity	NPD2421	Approved
0.7602	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7598	Intermediate Similarity	NPD4055	Discovery
0.7572	Intermediate Similarity	NPD1754	Clinical (unspecified phase)
0.7572	Intermediate Similarity	NPD1424	Approved
0.756	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.756	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7557	Intermediate Similarity	NPD4678	Approved
0.7557	Intermediate Similarity	NPD4675	Approved
0.7542	Intermediate Similarity	NPD4581	Clinical (unspecified phase)
0.7541	Intermediate Similarity	NPD2898	Approved
0.7514	Intermediate Similarity	NPD5677	Discontinued
0.7486	Intermediate Similarity	NPD6031	Approved
0.7486	Intermediate Similarity	NPD6030	Approved
0.7457	Intermediate Similarity	NPD3845	Phase 1
0.7457	Intermediate Similarity	NPD7124	Phase 2
0.7446	Intermediate Similarity	NPD4481	Phase 3
0.7432	Intermediate Similarity	NPD4010	Discontinued
0.7429	Intermediate Similarity	NPD6090	Discontinued
0.7414	Intermediate Similarity	NPD7598	Phase 2
0.7401	Intermediate Similarity	NPD4017	Approved
0.7399	Intermediate Similarity	NPD5241	Discontinued
0.7386	Intermediate Similarity	NPD3639	Approved
0.7386	Intermediate Similarity	NPD3641	Approved
0.7386	Intermediate Similarity	NPD3640	Phase 3
0.7377	Intermediate Similarity	NPD7802	Discontinued
0.7377	Intermediate Similarity	NPD6107	Approved
0.7374	Intermediate Similarity	NPD3450	Approved
0.7374	Intermediate Similarity	NPD2493	Approved
0.7374	Intermediate Similarity	NPD2494	Approved
0.7374	Intermediate Similarity	NPD3452	Approved
0.7365	Intermediate Similarity	NPD4475	Approved
0.7365	Intermediate Similarity	NPD4474	Approved
0.7347	Intermediate Similarity	NPD2975	Approved
0.7347	Intermediate Similarity	NPD2974	Approved
0.7347	Intermediate Similarity	NPD2973	Approved
0.7333	Intermediate Similarity	NPD5772	Approved
0.7333	Intermediate Similarity	NPD5773	Approved
0.7326	Intermediate Similarity	NPD42	Phase 2
0.7326	Intermediate Similarity	NPD6042	Phase 2
0.7323	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7318	Intermediate Similarity	NPD6072	Discontinued
0.7308	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD4005	Discontinued
0.7288	Intermediate Similarity	NPD2122	Discontinued
0.7286	Intermediate Similarity	NPD6997	Phase 2
0.7283	Intermediate Similarity	NPD5177	Phase 3
0.7273	Intermediate Similarity	NPD4123	Phase 3
0.7268	Intermediate Similarity	NPD2490	Approved
0.7268	Intermediate Similarity	NPD2488	Approved
0.7265	Intermediate Similarity	NPD8152	Approved
0.7265	Intermediate Similarity	NPD8153	Approved
0.7264	Intermediate Similarity	NPD4583	Approved
0.7264	Intermediate Similarity	NPD4582	Approved
0.725	Intermediate Similarity	NPD5006	Approved
0.725	Intermediate Similarity	NPD5005	Approved
0.7246	Intermediate Similarity	NPD7047	Phase 3
0.7241	Intermediate Similarity	NPD6748	Discontinued
0.7236	Intermediate Similarity	NPD4580	Approved
0.7214	Intermediate Similarity	NPD4002	Approved
0.7214	Intermediate Similarity	NPD4004	Approved
0.7207	Intermediate Similarity	NPD6523	Clinical (unspecified phase)
0.7202	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7202	Intermediate Similarity	NPD5718	Phase 2
0.7193	Intermediate Similarity	NPD2200	Suspended
0.7188	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7186	Intermediate Similarity	NPD3837	Clinical (unspecified phase)
0.7186	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7159	Intermediate Similarity	NPD6666	Approved
0.7159	Intermediate Similarity	NPD6667	Approved
0.7158	Intermediate Similarity	NPD6996	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD5312	Approved
0.7143	Intermediate Similarity	NPD5313	Approved
0.7143	Intermediate Similarity	NPD7466	Approved
0.7143	Intermediate Similarity	NPD7046	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD2968	Approved
0.7135	Intermediate Similarity	NPD2971	Approved
0.7126	Intermediate Similarity	NPD7045	Clinical (unspecified phase)
0.7119	Intermediate Similarity	NPD3124	Discontinued
0.7111	Intermediate Similarity	NPD8158	Clinical (unspecified phase)
0.7102	Intermediate Similarity	NPD3692	Discontinued
0.71	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7098	Intermediate Similarity	NPD6851	Approved
0.7098	Intermediate Similarity	NPD6853	Approved
0.7093	Intermediate Similarity	NPD7718	Clinical (unspecified phase)
0.7088	Intermediate Similarity	NPD7945	Clinical (unspecified phase)
0.7085	Intermediate Similarity	NPD6621	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD7132	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD4908	Phase 1
0.7068	Intermediate Similarity	NPD6297	Approved
0.7062	Intermediate Similarity	NPD2422	Clinical (unspecified phase)
0.705	Intermediate Similarity	NPD4420	Approved
0.7041	Intermediate Similarity	NPD4625	Phase 3
0.7037	Intermediate Similarity	NPD5602	Clinical (unspecified phase)
0.7029	Intermediate Similarity	NPD7037	Approved
0.7024	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD8051	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD7827	Phase 1
0.7018	Intermediate Similarity	NPD1613	Approved
0.7018	Intermediate Similarity	NPD2238	Phase 2
0.7018	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7016	Intermediate Similarity	NPD7479	Phase 2
0.7011	Intermediate Similarity	NPD1632	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD7493	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD6812	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD5976	Discontinued
0.6995	Remote Similarity	NPD7590	Clinical (unspecified phase)
0.6995	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD6111	Discontinued
0.6994	Remote Similarity	NPD6896	Approved
0.6994	Remote Similarity	NPD6895	Approved
0.6989	Remote Similarity	NPD4236	Phase 3
0.6989	Remote Similarity	NPD4237	Approved
0.6989	Remote Similarity	NPD3060	Approved
0.6989	Remote Similarity	NPD5709	Phase 3
0.6983	Remote Similarity	NPD4160	Clinical (unspecified phase)
0.6968	Remote Similarity	NPD4166	Phase 2
0.6966	Remote Similarity	NPD6783	Clinical (unspecified phase)
0.6963	Remote Similarity	NPD4873	Discontinued
0.6959	Remote Similarity	NPD3534	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD4585	Approved
0.6954	Remote Similarity	NPD1753	Discontinued
0.6952	Remote Similarity	NPD4666	Phase 3
0.6947	Remote Similarity	NPD5938	Phase 3
0.6944	Remote Similarity	NPD5261	Clinical (unspecified phase)
0.6941	Remote Similarity	NPD2669	Clinical (unspecified phase)
0.694	Remote Similarity	NPD7438	Suspended
0.694	Remote Similarity	NPD5090	Approved
0.694	Remote Similarity	NPD5089	Approved
0.6935	Remote Similarity	NPD8005	Clinical (unspecified phase)
0.6927	Remote Similarity	NPD4040	Phase 1
0.6916	Remote Similarity	NPD7907	Approved
0.6915	Remote Similarity	NPD6284	Clinical (unspecified phase)
0.6911	Remote Similarity	NPD7177	Discontinued
0.691	Remote Similarity	NPD2677	Approved
0.6906	Remote Similarity	NPD7427	Discontinued
0.6904	Remote Similarity	NPD7291	Discontinued
0.6893	Remote Similarity	NPD4162	Approved
0.6889	Remote Similarity	NPD7020	Approved
0.6889	Remote Similarity	NPD7019	Approved
0.6882	Remote Similarity	NPD7773	Phase 2
0.6875	Remote Similarity	NPD7030	Discontinued
0.6875	Remote Similarity	NPD2029	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD5844	Phase 1
0.6865	Remote Similarity	NPD2978	Approved
0.6865	Remote Similarity	NPD2977	Approved
0.6862	Remote Similarity	NPD2904	Discontinued
0.686	Remote Similarity	NPD7477	Discontinued
0.6854	Remote Similarity	NPD6331	Phase 2
0.6854	Remote Similarity	NPD6658	Clinical (unspecified phase)
0.6851	Remote Similarity	NPD7527	Clinical (unspecified phase)
0.6851	Remote Similarity	NPD52	Approved
0.6851	Remote Similarity	NPD3647	Clinical (unspecified phase)
0.6851	Remote Similarity	NPD7526	Approved
0.685	Remote Similarity	NPD7125	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