NPASS Compound

Structure

NPC469792 OpenBabel07101718202D 44 50 0 0 1 0 0 0 0 0999 V2000 -3.0892 3.9901 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3821 -1.7170 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9742 -1.6530 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7880 2.0448 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6463 2.4497 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2094 4.7248 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4894 2.9069 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4142 3.1197 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9449 3.7781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0681 -0.9068 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2481 1.7830 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6605 -0.5174 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2481 2.7830 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4199 1.0695 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1804 3.4075 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0116 4.1757 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3821 0.2830 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1275 -1.0087 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6501 1.2830 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6483 1.7407 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6601 3.8891 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3821 1.2830 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4346 -0.5884 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9772 3.6780 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5161 1.7830 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9860 0.5088 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5161 2.7830 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0072 3.5338 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6948 4.2362 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5161 -0.2170 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6501 0.2830 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6101 -0.9528 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3936 0.1194 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3997 -0.4768 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7067 -0.0566 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6195 0.1904 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -2.3821 3.2830 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.2763 2.5707 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5946 -0.3696 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.4582 3.6657 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5161 -1.2170 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0201 -1.7602 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3826 4.0641 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 37 1 0 0 0 0 2 41 1 0 0 0 0 3 42 1 0 0 0 0 4 7 1 0 0 0 0 4 20 2 0 0 0 0 5 8 2 0 0 0 0 5 20 1 0 0 0 0 6 9 2 0 0 0 0 6 21 1 0 0 0 0 7 24 2 0 0 0 0 8 24 1 0 0 0 0 9 28 1 0 0 0 0 10 12 2 0 0 0 0 10 23 1 0 0 0 0 11 13 1 0 0 0 0 11 22 1 0 0 0 0 12 36 1 0 0 0 0 13 37 1 0 0 0 0 14 20 1 0 0 0 0 14 26 1 0 0 0 0 15 21 1 0 0 0 0 16 21 2 0 0 0 0 16 29 1 0 0 0 0 17 22 2 0 0 0 0 17 30 1 0 0 0 0 18 23 2 0 0 0 0 18 32 1 0 0 0 0 19 25 2 0 0 0 0 19 31 1 0 0 0 0 22 25 1 0 0 0 0 23 33 1 0 0 0 0 24 43 1 0 0 0 0 25 27 1 0 0 0 0 26 33 1 0 0 0 0 26 36 2 0 0 0 0 27 15 1 6 0 0 0 27 37 1 0 0 0 0 28 29 2 0 0 0 0 28 38 1 0 0 0 0 29 43 1 0 0 0 0 30 31 2 0 0 0 0 30 41 1 0 0 0 0 31 44 1 0 0 0 0 32 34 2 0 0 0 0 32 42 1 0 0 0 0 33 35 2 0 0 0 0 34 35 1 0 0 0 0 34 39 1 0 0 0 0 35 44 1 0 0 0 0 37 40 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	592.22
Volume:	600.635
LogP:	4.649
LogD:	2.717
LogS:	-1.926
# Rotatable Bonds:	2
TPSA:	113.33
# H-Bond Aceptor:	9
# H-Bond Donor:	2
# Rings:	8
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.168
Synthetic Accessibility Score:	6.134
Fsp3:	0.229
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.946
MDCK Permeability:	2.0837369447690435e-05
Pgp-inhibitor:	0.013
Pgp-substrate:	0.998
Human Intestinal Absorption (HIA):	0.426
20% Bioavailability (F20%):	0.989
30% Bioavailability (F30%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.008
Plasma Protein Binding (PPB):	97.04715728759766%
Volume Distribution (VD):	0.63
Pgp-substrate:	3.9787330627441406%

ADMET: Metabolism

CYP1A2-inhibitor:	0.071
CYP1A2-substrate:	0.916
CYP2C19-inhibitor:	0.487
CYP2C19-substrate:	0.569
CYP2C9-inhibitor:	0.738
CYP2C9-substrate:	0.845
CYP2D6-inhibitor:	0.004
CYP2D6-substrate:	0.879
CYP3A4-inhibitor:	0.494
CYP3A4-substrate:	0.94

ADMET: Excretion

Clearance (CL):	7.475
Half-life (T1/2):	0.931

ADMET: Toxicity

hERG Blockers:	0.456
Human Hepatotoxicity (H-HT):	0.088
Drug-inuced Liver Injury (DILI):	0.035
AMES Toxicity:	0.261
Rat Oral Acute Toxicity:	0.879
Maximum Recommended Daily Dose:	0.994
Skin Sensitization:	0.692
Carcinogencity:	0.255
Eye Corrosion:	0.003
Eye Irritation:	0.022
Respiratory Toxicity:	0.247

Download Data

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

Natural Product: NPC469792

Natural Product ID:	NPC469792
*Common Name:**	Racemosinine C
IUPAC Name:	n.a.
Synonyms:	Racemosinine C
Standard InCHIKey:	DTBYELYRIBFWEE-YNJTUNHHSA-N
Standard InCHI:	InChI=1S/C35H32N2O7/c1-37(40)13-11-22-17-30(41-2)31-19-25(22)27(37)15-21-6-9-28(38)29(16-21)43-24-7-4-20(5-8-24)14-26-33-23(10-12-36-26)18-32(42-3)34(39)35(33)44-31/h4-10,12,16-19,27,38-39H,11,13-15H2,1-3H3/t27-,37?/m1/s1
SMILES:	C[N+]1(CCC2=CC(=C3C=C2C1CC4=CC(=C(C=C4)O)OC5=CC=C(CC6=NC=CC7=CC(=C(C(=C67)O3)O)OC)C=C5)OC)[O-]
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1172572
PubChem CID:	46872350
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
NPO18410	Cyclea racemosa	Species	Menispermaceae	Eukaryota	roots	n.a.	n.a.	PMID[20593839]
NPO18410	Cyclea racemosa	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18410	Cyclea racemosa	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18410	Cyclea racemosa	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO18410	Cyclea racemosa	Species	Menispermaceae	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	3

Activity Type	# Activity
Cell Line	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT180	Cell Line	HCT-8	Homo sapiens	IC50	>	10000.0	nM	PMID[543733]
NPT181	Cell Line	Bel-7402	Homo sapiens	IC50	>	10000.0	nM	PMID[543733]
NPT179	Cell Line	A2780	Homo sapiens	IC50	>	10000.0	nM	PMID[543733]

☑ 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 NPC469792 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	596
0.1-0.2	3091
0.2-0.3	13249
0.3-0.4	4712
0.4-0.5	9826
0.5-0.6	9037
0.6-0.7	1829
0.7-0.8	315
0.8-0.85	30
0.85-0.9	7
0.9-0.95	1
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9019	High Similarity	NPC201508
0.8848	High Similarity	NPC255800
0.8848	High Similarity	NPC96584
0.8768	High Similarity	NPC473822
0.8349	Intermediate Similarity	NPC122463
0.8271	Intermediate Similarity	NPC202605
0.8271	Intermediate Similarity	NPC112206
0.8091	Intermediate Similarity	NPC174049
0.8038	Intermediate Similarity	NPC224928
0.8009	Intermediate Similarity	NPC290689
0.7944	Intermediate Similarity	NPC36229
0.7944	Intermediate Similarity	NPC476581
0.7944	Intermediate Similarity	NPC16452
0.792	Intermediate Similarity	NPC476997
0.7885	Intermediate Similarity	NPC476998
0.7885	Intermediate Similarity	NPC476996
0.7857	Intermediate Similarity	NPC471113
0.7847	Intermediate Similarity	NPC195268
0.7847	Intermediate Similarity	NPC133140
0.7841	Intermediate Similarity	NPC476994
0.7814	Intermediate Similarity	NPC469440
0.7804	Intermediate Similarity	NPC31930
0.7778	Intermediate Similarity	NPC61350
0.7758	Intermediate Similarity	NPC173080
0.7714	Intermediate Similarity	NPC469390
0.771	Intermediate Similarity	NPC4071
0.771	Intermediate Similarity	NPC476582
0.771	Intermediate Similarity	NPC476578
0.7692	Intermediate Similarity	NPC202768
0.7692	Intermediate Similarity	NPC296482
0.7692	Intermediate Similarity	NPC53069
0.7689	Intermediate Similarity	NPC85381
0.7682	Intermediate Similarity	NPC476995
0.7678	Intermediate Similarity	NPC41122
0.7678	Intermediate Similarity	NPC318805
0.7669	Intermediate Similarity	NPC15406
0.7617	Intermediate Similarity	NPC234318
0.7561	Intermediate Similarity	NPC10871
0.7544	Intermediate Similarity	NPC118121
0.7534	Intermediate Similarity	NPC96405
0.7534	Intermediate Similarity	NPC171409
0.7512	Intermediate Similarity	NPC477019
0.7511	Intermediate Similarity	NPC119134
0.7511	Intermediate Similarity	NPC217554
0.749	Intermediate Similarity	NPC284141
0.7488	Intermediate Similarity	NPC473053
0.7468	Intermediate Similarity	NPC476999
0.7466	Intermediate Similarity	NPC313189
0.7458	Intermediate Similarity	NPC107123
0.7455	Intermediate Similarity	NPC137929
0.7455	Intermediate Similarity	NPC164374
0.7438	Intermediate Similarity	NPC134637
0.7426	Intermediate Similarity	NPC11408
0.7407	Intermediate Similarity	NPC77878
0.7406	Intermediate Similarity	NPC249996
0.7395	Intermediate Similarity	NPC289786
0.7393	Intermediate Similarity	NPC476202
0.7378	Intermediate Similarity	NPC251160
0.7373	Intermediate Similarity	NPC90875
0.7368	Intermediate Similarity	NPC204446
0.7362	Intermediate Similarity	NPC233334
0.7349	Intermediate Similarity	NPC141915
0.7349	Intermediate Similarity	NPC280964
0.7349	Intermediate Similarity	NPC114335
0.7346	Intermediate Similarity	NPC195538
0.7345	Intermediate Similarity	NPC266931
0.7342	Intermediate Similarity	NPC295228
0.7336	Intermediate Similarity	NPC183537
0.7325	Intermediate Similarity	NPC473513
0.7309	Intermediate Similarity	NPC135549
0.7301	Intermediate Similarity	NPC316981
0.7298	Intermediate Similarity	NPC129897
0.7297	Intermediate Similarity	NPC210256
0.7293	Intermediate Similarity	NPC100079
0.7293	Intermediate Similarity	NPC23614
0.7273	Intermediate Similarity	NPC234197
0.7269	Intermediate Similarity	NPC474594
0.7269	Intermediate Similarity	NPC162530
0.7261	Intermediate Similarity	NPC148409
0.7237	Intermediate Similarity	NPC235076
0.723	Intermediate Similarity	NPC8836
0.723	Intermediate Similarity	NPC222661
0.723	Intermediate Similarity	NPC181796
0.723	Intermediate Similarity	NPC328155
0.723	Intermediate Similarity	NPC290582
0.723	Intermediate Similarity	NPC258657
0.723	Intermediate Similarity	NPC290005
0.723	Intermediate Similarity	NPC90998
0.723	Intermediate Similarity	NPC182052
0.723	Intermediate Similarity	NPC239824
0.723	Intermediate Similarity	NPC223690
0.723	Intermediate Similarity	NPC285931
0.723	Intermediate Similarity	NPC54654
0.723	Intermediate Similarity	NPC279228
0.723	Intermediate Similarity	NPC251735
0.723	Intermediate Similarity	NPC7715
0.723	Intermediate Similarity	NPC49075
0.723	Intermediate Similarity	NPC185639
0.723	Intermediate Similarity	NPC217748
0.723	Intermediate Similarity	NPC229373
0.723	Intermediate Similarity	NPC271013
0.723	Intermediate Similarity	NPC311973
0.723	Intermediate Similarity	NPC104196
0.723	Intermediate Similarity	NPC42663
0.723	Intermediate Similarity	NPC15414
0.7229	Intermediate Similarity	NPC469439
0.7222	Intermediate Similarity	NPC214980
0.722	Intermediate Similarity	NPC47059
0.722	Intermediate Similarity	NPC165349
0.722	Intermediate Similarity	NPC274291
0.722	Intermediate Similarity	NPC329708
0.722	Intermediate Similarity	NPC264166
0.722	Intermediate Similarity	NPC118832
0.7203	Intermediate Similarity	NPC24019
0.7196	Intermediate Similarity	NPC167116
0.7196	Intermediate Similarity	NPC254441
0.7196	Intermediate Similarity	NPC274716
0.7193	Intermediate Similarity	NPC236668
0.7186	Intermediate Similarity	NPC46451
0.7183	Intermediate Similarity	NPC286119
0.7176	Intermediate Similarity	NPC275680
0.7176	Intermediate Similarity	NPC22115
0.717	Intermediate Similarity	NPC470474
0.7167	Intermediate Similarity	NPC280272
0.7162	Intermediate Similarity	NPC146976
0.7155	Intermediate Similarity	NPC54066
0.715	Intermediate Similarity	NPC30779
0.7149	Intermediate Similarity	NPC200888
0.7149	Intermediate Similarity	NPC210296
0.7131	Intermediate Similarity	NPC124313
0.713	Intermediate Similarity	NPC116465
0.713	Intermediate Similarity	NPC66815
0.713	Intermediate Similarity	NPC212237
0.7129	Intermediate Similarity	NPC204908
0.7129	Intermediate Similarity	NPC83198
0.7119	Intermediate Similarity	NPC84164
0.7119	Intermediate Similarity	NPC207283
0.7118	Intermediate Similarity	NPC271215
0.7118	Intermediate Similarity	NPC149471
0.7111	Intermediate Similarity	NPC470164
0.7111	Intermediate Similarity	NPC323345
0.7089	Intermediate Similarity	NPC246381
0.7083	Intermediate Similarity	NPC16357
0.7083	Intermediate Similarity	NPC277351
0.7083	Intermediate Similarity	NPC95426
0.7083	Intermediate Similarity	NPC302245
0.7083	Intermediate Similarity	NPC66083
0.7078	Intermediate Similarity	NPC99891
0.7078	Intermediate Similarity	NPC279401
0.7078	Intermediate Similarity	NPC79293
0.7074	Intermediate Similarity	NPC203168
0.7064	Intermediate Similarity	NPC82457
0.7064	Intermediate Similarity	NPC175890
0.7064	Intermediate Similarity	NPC206900
0.7064	Intermediate Similarity	NPC48490
0.7064	Intermediate Similarity	NPC11296
0.7064	Intermediate Similarity	NPC274661
0.7061	Intermediate Similarity	NPC219664
0.7061	Intermediate Similarity	NPC188420
0.7051	Intermediate Similarity	NPC65312
0.7051	Intermediate Similarity	NPC139783
0.7048	Intermediate Similarity	NPC66573
0.7048	Intermediate Similarity	NPC18348
0.7035	Intermediate Similarity	NPC472111
0.7035	Intermediate Similarity	NPC304183
0.7034	Intermediate Similarity	NPC473449
0.7033	Intermediate Similarity	NPC264850
0.7033	Intermediate Similarity	NPC13916
0.7032	Intermediate Similarity	NPC191132
0.7032	Intermediate Similarity	NPC60295
0.7028	Intermediate Similarity	NPC152680
0.7028	Intermediate Similarity	NPC190783
0.7028	Intermediate Similarity	NPC232386
0.7027	Intermediate Similarity	NPC127085
0.7023	Intermediate Similarity	NPC62069
0.7021	Intermediate Similarity	NPC210434
0.7004	Intermediate Similarity	NPC474595
0.7	Intermediate Similarity	NPC478093
0.7	Intermediate Similarity	NPC24260
0.6986	Remote Similarity	NPC24465
0.6983	Remote Similarity	NPC108342
0.6968	Remote Similarity	NPC30182
0.6968	Remote Similarity	NPC473589
0.6968	Remote Similarity	NPC478092
0.6968	Remote Similarity	NPC478091
0.6955	Remote Similarity	NPC189903
0.6955	Remote Similarity	NPC182907
0.6948	Remote Similarity	NPC283152
0.6944	Remote Similarity	NPC318068
0.6943	Remote Similarity	NPC469589
0.6926	Remote Similarity	NPC166722
0.692	Remote Similarity	NPC302807
0.692	Remote Similarity	NPC287437
0.6916	Remote Similarity	NPC285558
0.6901	Remote Similarity	NPC227060
0.6901	Remote Similarity	NPC317439
0.6901	Remote Similarity	NPC63646
0.6901	Remote Similarity	NPC276890
0.6901	Remote Similarity	NPC10908
0.6901	Remote Similarity	NPC115284

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 NPC469792 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	313
0.1-0.2	667
0.2-0.3	989
0.3-0.4	1662
0.4-0.5	2641
0.5-0.6	2128
0.6-0.7	666
0.7-0.8	78
0.8-0.85	6
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7847	Intermediate Similarity	NPD3922	Approved
0.7847	Intermediate Similarity	NPD3923	Approved
0.7847	Intermediate Similarity	NPD3921	Approved
0.7847	Intermediate Similarity	NPD3924	Approved
0.7725	Intermediate Similarity	NPD6361	Phase 2
0.7706	Intermediate Similarity	NPD6494	Phase 2
0.7692	Intermediate Similarity	NPD3815	Phase 1
0.7692	Intermediate Similarity	NPD3816	Phase 1
0.7585	Intermediate Similarity	NPD3386	Phase 2
0.7559	Intermediate Similarity	NPD4551	Phase 2
0.7443	Intermediate Similarity	NPD6477	Clinical (unspecified phase)
0.7398	Intermediate Similarity	NPD7169	Suspended
0.7378	Intermediate Similarity	NPD7069	Discontinued
0.7349	Intermediate Similarity	NPD6569	Phase 2
0.7333	Intermediate Similarity	NPD1483	Discontinued
0.7321	Intermediate Similarity	NPD3920	Phase 2
0.7257	Intermediate Similarity	NPD7558	Phase 2
0.7251	Intermediate Similarity	NPD7414	Clinical (unspecified phase)
0.7243	Intermediate Similarity	NPD6257	Clinical (unspecified phase)
0.723	Intermediate Similarity	NPD8054	Approved
0.723	Intermediate Similarity	NPD8053	Approved
0.7222	Intermediate Similarity	NPD2334	Discontinued
0.722	Intermediate Similarity	NPD32	Approved
0.722	Intermediate Similarity	NPD4033	Approved
0.722	Intermediate Similarity	NPD4034	Approved
0.722	Intermediate Similarity	NPD4122	Approved
0.722	Intermediate Similarity	NPD4039	Approved
0.722	Intermediate Similarity	NPD4038	Approved
0.722	Intermediate Similarity	NPD4036	Approved
0.722	Intermediate Similarity	NPD4037	Approved
0.722	Intermediate Similarity	NPD4035	Approved
0.722	Intermediate Similarity	NPD31	Approved
0.7195	Intermediate Similarity	NPD6503	Clinical (unspecified phase)
0.7186	Intermediate Similarity	NPD3763	Approved
0.7168	Intermediate Similarity	NPD4437	Phase 3
0.7166	Intermediate Similarity	NPD7859	Phase 2
0.7156	Intermediate Similarity	NPD7222	Phase 2
0.715	Intermediate Similarity	NPD6872	Clinical (unspecified phase)
0.7149	Intermediate Similarity	NPD7676	Clinical (unspecified phase)
0.7149	Intermediate Similarity	NPD7675	Phase 3
0.7149	Intermediate Similarity	NPD7674	Phase 3
0.7131	Intermediate Similarity	NPD6230	Discontinued
0.713	Intermediate Similarity	NPD5612	Discontinued
0.7119	Intermediate Similarity	NPD4875	Phase 3
0.7119	Intermediate Similarity	NPD4876	Phase 3
0.7117	Intermediate Similarity	NPD4396	Clinical (unspecified phase)
0.7116	Intermediate Similarity	NPD4375	Approved
0.7105	Intermediate Similarity	NPD4131	Phase 3
0.7085	Intermediate Similarity	NPD6525	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD6963	Approved
0.7083	Intermediate Similarity	NPD6964	Approved
0.7075	Intermediate Similarity	NPD1620	Clinical (unspecified phase)
0.7066	Intermediate Similarity	NPD7729	Clinical (unspecified phase)
0.7046	Intermediate Similarity	NPD6553	Clinical (unspecified phase)
0.7028	Intermediate Similarity	NPD5751	Clinical (unspecified phase)
0.7009	Intermediate Similarity	NPD5930	Phase 3
0.6991	Remote Similarity	NPD4889	Approved
0.6984	Remote Similarity	NPD8091	Phase 3
0.6983	Remote Similarity	NPD8510	Clinical (unspecified phase)
0.6982	Remote Similarity	NPD1622	Discontinued
0.6974	Remote Similarity	NPD5863	Clinical (unspecified phase)
0.6967	Remote Similarity	NPD7885	Phase 2
0.6967	Remote Similarity	NPD7886	Phase 2
0.696	Remote Similarity	NPD5530	Phase 1
0.6934	Remote Similarity	NPD1923	Clinical (unspecified phase)
0.6934	Remote Similarity	NPD5602	Clinical (unspecified phase)
0.693	Remote Similarity	NPD7453	Approved
0.693	Remote Similarity	NPD7452	Approved
0.6905	Remote Similarity	NPD8442	Discontinued
0.6901	Remote Similarity	NPD8251	Approved
0.6901	Remote Similarity	NPD8099	Discontinued
0.6901	Remote Similarity	NPD8252	Approved
0.69	Remote Similarity	NPD5658	Approved
0.6898	Remote Similarity	NPD7025	Clinical (unspecified phase)
0.6895	Remote Similarity	NPD4021	Phase 2
0.6892	Remote Similarity	NPD3395	Approved
0.6892	Remote Similarity	NPD3396	Approved
0.689	Remote Similarity	NPD7955	Approved
0.689	Remote Similarity	NPD7956	Approved
0.6889	Remote Similarity	NPD6219	Discontinued
0.6869	Remote Similarity	NPD8156	Discontinued
0.6862	Remote Similarity	NPD7426	Phase 1
0.686	Remote Similarity	NPD6773	Clinical (unspecified phase)
0.6856	Remote Similarity	NPD1392	Approved
0.6855	Remote Similarity	NPD4350	Approved
0.6855	Remote Similarity	NPD4349	Approved
0.6852	Remote Similarity	NPD4203	Approved
0.6852	Remote Similarity	NPD4204	Approved
0.6851	Remote Similarity	NPD6568	Discontinued
0.6842	Remote Similarity	NPD4795	Phase 2
0.6835	Remote Similarity	NPD6298	Discontinued
0.683	Remote Similarity	NPD2952	Discontinued
0.6816	Remote Similarity	NPD6861	Clinical (unspecified phase)
0.6812	Remote Similarity	NPD4305	Clinical (unspecified phase)
0.681	Remote Similarity	NPD4502	Phase 2
0.6795	Remote Similarity	NPD5902	Approved
0.6795	Remote Similarity	NPD5903	Approved
0.6792	Remote Similarity	NPD4724	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD3477	Phase 2
0.6786	Remote Similarity	NPD3478	Clinical (unspecified phase)
0.6784	Remote Similarity	NPD7134	Clinical (unspecified phase)
0.6773	Remote Similarity	NPD8350	Clinical (unspecified phase)
0.677	Remote Similarity	NPD7862	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD5147	Discontinued
0.6757	Remote Similarity	NPD7803	Approved
0.6754	Remote Similarity	NPD7123	Suspended
0.6753	Remote Similarity	NPD2739	Clinical (unspecified phase)
0.6739	Remote Similarity	NPD5601	Phase 2
0.6735	Remote Similarity	NPD7807	Clinical (unspecified phase)
0.6732	Remote Similarity	NPD7708	Approved
0.673	Remote Similarity	NPD7682	Approved
0.673	Remote Similarity	NPD7684	Approved
0.6723	Remote Similarity	NPD5070	Clinical (unspecified phase)
0.6722	Remote Similarity	NPD5640	Discontinued
0.671	Remote Similarity	NPD7263	Phase 2
0.6697	Remote Similarity	NPD1034	Phase 3
0.6697	Remote Similarity	NPD1033	Clinical (unspecified phase)
0.6696	Remote Similarity	NPD1304	Clinical (unspecified phase)
0.6696	Remote Similarity	NPD1038	Approved
0.6694	Remote Similarity	NPD5905	Phase 1
0.6681	Remote Similarity	NPD5944	Phase 1
0.6681	Remote Similarity	NPD7571	Clinical (unspecified phase)
0.6681	Remote Similarity	NPD5945	Phase 1
0.6667	Remote Similarity	NPD7417	Discontinued
0.6667	Remote Similarity	NPD4989	Phase 2
0.6667	Remote Similarity	NPD4418	Discontinued
0.6667	Remote Similarity	NPD1740	Approved
0.6667	Remote Similarity	NPD1739	Approved
0.6667	Remote Similarity	NPD3003	Approved
0.6667	Remote Similarity	NPD1954	Phase 1
0.6667	Remote Similarity	NPD1856	Discontinued
0.6653	Remote Similarity	NPD6856	Discontinued
0.6652	Remote Similarity	NPD4372	Phase 1
0.664	Remote Similarity	NPD5833	Phase 1
0.6639	Remote Similarity	NPD8052	Clinical (unspecified phase)
0.6636	Remote Similarity	NPD1032	Phase 2
0.6626	Remote Similarity	NPD4984	Phase 2
0.6623	Remote Similarity	NPD4052	Clinical (unspecified phase)
0.6623	Remote Similarity	NPD3837	Clinical (unspecified phase)
0.6612	Remote Similarity	NPD7719	Discontinued
0.6611	Remote Similarity	NPD3514	Clinical (unspecified phase)
0.6605	Remote Similarity	NPD1078	Clinical (unspecified phase)
0.6599	Remote Similarity	NPD2757	Phase 2
0.6597	Remote Similarity	NPD7823	Clinical (unspecified phase)
0.6596	Remote Similarity	NPD5067	Phase 2
0.6596	Remote Similarity	NPD5066	Phase 2
0.6593	Remote Similarity	NPD3810	Clinical (unspecified phase)
0.6587	Remote Similarity	NPD7967	Discontinued
0.6585	Remote Similarity	NPD7796	Approved
0.6585	Remote Similarity	NPD7797	Approved
0.6579	Remote Similarity	NPD7889	Clinical (unspecified phase)
0.6577	Remote Similarity	NPD5256	Discontinued
0.6571	Remote Similarity	NPD8512	Phase 3
0.6571	Remote Similarity	NPD7589	Clinical (unspecified phase)
0.6564	Remote Similarity	NPD6550	Discontinued
0.6561	Remote Similarity	NPD7313	Approved
0.6561	Remote Similarity	NPD5083	Clinical (unspecified phase)
0.6561	Remote Similarity	NPD7312	Approved
0.6561	Remote Similarity	NPD7311	Approved
0.6561	Remote Similarity	NPD7310	Approved
0.6556	Remote Similarity	NPD5506	Approved
0.6556	Remote Similarity	NPD5507	Approved
0.6553	Remote Similarity	NPD6262	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD3397	Phase 2
0.655	Remote Similarity	NPD5999	Phase 2
0.655	Remote Similarity	NPD1768	Approved
0.6549	Remote Similarity	NPD5575	Clinical (unspecified phase)
0.6542	Remote Similarity	NPD7194	Discontinued
0.6542	Remote Similarity	NPD6501	Approved
0.6542	Remote Similarity	NPD6500	Approved
0.654	Remote Similarity	NPD7673	Phase 3
0.6538	Remote Similarity	NPD7672	Approved
0.6538	Remote Similarity	NPD7671	Approved
0.6535	Remote Similarity	NPD7948	Phase 1
0.6532	Remote Similarity	NPD6344	Clinical (unspecified phase)
0.6532	Remote Similarity	NPD7309	Approved
0.6531	Remote Similarity	NPD7555	Discontinued
0.6529	Remote Similarity	NPD6824	Clinical (unspecified phase)
0.652	Remote Similarity	NPD6491	Clinical (unspecified phase)
0.6513	Remote Similarity	NPD6140	Clinical (unspecified phase)
0.6509	Remote Similarity	NPD4044	Discontinued
0.65	Remote Similarity	NPD8109	Clinical (unspecified phase)
0.6494	Remote Similarity	NPD2929	Clinical (unspecified phase)
0.6494	Remote Similarity	NPD6592	Clinical (unspecified phase)
0.6492	Remote Similarity	NPD4080	Discontinued
0.6489	Remote Similarity	NPD8063	Discontinued
0.6484	Remote Similarity	NPD6243	Phase 3
0.6484	Remote Similarity	NPD6244	Phase 3
0.6484	Remote Similarity	NPD4072	Approved
0.6484	Remote Similarity	NPD4071	Approved
0.6482	Remote Similarity	NPD7620	Phase 2
0.6481	Remote Similarity	NPD6071	Discontinued
0.6481	Remote Similarity	NPD3946	Clinical (unspecified phase)
0.6478	Remote Similarity	NPD2175	Phase 3
0.6478	Remote Similarity	NPD4996	Approved
0.6478	Remote Similarity	NPD2176	Approved
0.6478	Remote Similarity	NPD2177	Approved
0.6478	Remote Similarity	NPD4995	Approved
0.6475	Remote Similarity	NPD7586	Clinical (unspecified phase)
0.6473	Remote Similarity	NPD4926	Clinical (unspecified phase)

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data