NPASS Compound

Structure

CID129721 OpenBabel06191715482D 22 25 0 0 1 0 0 0 0 0999 V2000 1.0540 2.3360 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0606 2.4504 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8214 1.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8214 2.3452 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6942 0.3601 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2170 1.2983 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2170 2.6941 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1250 2.9098 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6092 0.1691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4863 1.3383 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5352 2.3452 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9511 -0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6126 1.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2024 1.0827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6126 2.3452 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5387 3.1254 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2079 0.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5352 1.6473 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.2024 2.9098 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.5387 4.1254 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 0 0 0 3 4 2 0 0 0 0 3 6 1 0 0 0 0 4 7 1 0 0 0 0 5 10 1 0 0 0 0 5 12 1 0 0 0 0 6 14 2 0 0 0 0 7 16 2 0 0 0 0 8 11 1 0 0 0 0 8 17 1 0 0 0 0 9 13 2 0 0 0 0 9 15 1 0 0 0 0 10 19 1 0 0 0 0 11 19 1 0 0 0 0 12 21 1 0 0 0 0 13 21 1 0 0 0 0 14 15 1 0 0 0 0 14 16 1 0 0 0 0 15 18 2 0 0 0 0 16 20 1 0 0 0 0 17 20 2 3 0 0 0 17 22 1 0 0 0 0 18 19 1 0 0 0 0 18 21 1 0 0 0 0 19 2 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	294.17
Volume:	317.919
LogP:	3.039
LogD:	2.859
LogS:	-4.637
# Rotatable Bonds:	1
TPSA:	34.03
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.834
Synthetic Accessibility Score:	3.76
Fsp3:	0.421
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.611
MDCK Permeability:	1.8610262486618012e-05
Pgp-inhibitor:	0.969
Pgp-substrate:	0.009
Human Intestinal Absorption (HIA):	0.002
20% Bioavailability (F20%):	0.936
30% Bioavailability (F30%):	0.863

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.529
Plasma Protein Binding (PPB):	91.1626205444336%
Volume Distribution (VD):	1.313
Pgp-substrate:	6.307058811187744%

ADMET: Metabolism

CYP1A2-inhibitor:	0.826
CYP1A2-substrate:	0.917
CYP2C19-inhibitor:	0.805
CYP2C19-substrate:	0.378
CYP2C9-inhibitor:	0.612
CYP2C9-substrate:	0.5
CYP2D6-inhibitor:	0.704
CYP2D6-substrate:	0.874
CYP3A4-inhibitor:	0.892
CYP3A4-substrate:	0.414

ADMET: Excretion

Clearance (CL):	2.639
Half-life (T1/2):	0.576

ADMET: Toxicity

hERG Blockers:	0.257
Human Hepatotoxicity (H-HT):	0.712
Drug-inuced Liver Injury (DILI):	0.47
AMES Toxicity:	0.702
Rat Oral Acute Toxicity:	0.812
Maximum Recommended Daily Dose:	0.353
Skin Sensitization:	0.086
Carcinogencity:	0.691
Eye Corrosion:	0.003
Eye Irritation:	0.015
Respiratory Toxicity:	0.618

Download Data

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

Natural Product: NPC129721

Natural Product ID:	NPC129721
*Common Name:**	Rhazinilam
IUPAC Name:	n.a.
Synonyms:	Rhazinilam
Standard InCHIKey:	VLQAFTDOIRUYSZ-LJQANCHMSA-N
Standard InCHI:	InChI=1S/C19H22N2O/c1-2-19-10-5-12-21-13-9-15(18(19)21)14-6-3-4-7-16(14)20-17(22)8-11-19/h3-4,6-7,9,13H,2,5,8,10-12H2,1H3,(H,20,22)/t19-/m1/s1
SMILES:	CC[C@@]12CCCn3ccc(-c4ccccc4N=C(CC1)O)c23
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL302501
PubChem CID:	11312435
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids

*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
NPO18923	Coleus xanthanthus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12027731]
NPO2700	Kopsia arborea	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17665953]
NPO19270	Kopsia singapurensis	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17939738]
NPO19270	Kopsia singapurensis	Species	Apocynaceae	Eukaryota	leaf and stem-bark	Pahang, Malaysia	1996-JUL	PMID[18078327]
NPO2700	Kopsia arborea	Species	Apocynaceae	Eukaryota	n.a.	Yunnan, China	n.a.	PMID[19133778]
NPO6664	Kopsia officinalis	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[28218521]
NPO2700	Kopsia arborea	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31241923]
NPO18923	Coleus xanthanthus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO6664	Kopsia officinalis	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21640	Pygmaeopremna herbacea	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[TCMID]
NPO18923	Coleus xanthanthus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20028	Lethariella sernanderi	Species	Parmeliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19270	Kopsia singapurensis	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18923	Coleus xanthanthus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17662	Scutellaria glabrata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17897	Streptomyces albospinus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO21313	Rabdosia lasiocarpa	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6664	Kopsia officinalis	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21640	Pygmaeopremna herbacea	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO7972	Solaster endeca	Species	Solasteridae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13485	Prismatomeris sessiliflora	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2700	Kopsia arborea	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8358	Senecio halimifolius	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	10
Others	16

Activity Type	# Activity
Cell Line	20
NON-MOLECULAR	2
Others	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	IC50	=	650.0	nM	PMID[575363]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	350.0	nM	PMID[575364]
NPT139	Cell Line	HT-29	Homo sapiens	IC50	=	350.0	nM	PMID[575364]
NPT5171	Cell Line	Human T-cell line		Activity	=	68.8	%	PMID[575365]
NPT5171	Cell Line	Human T-cell line		Activity	=	70.3	%	PMID[575365]
NPT5171	Cell Line	Human T-cell line		Activity	=	69.3	%	PMID[575365]
NPT5171	Cell Line	Human T-cell line		Activity	=	41.1	%	PMID[575365]
NPT5171	Cell Line	Human T-cell line		Activity	=	42.4	%	PMID[575365]
NPT5171	Cell Line	Human T-cell line		Activity	=	41.6	%	PMID[575365]
NPT5171	Cell Line	Human T-cell line		Activity	=	40.3	%	PMID[575365]
NPT5171	Cell Line	Human T-cell line		Activity	=	17.6	%	PMID[575365]
NPT5171	Cell Line	Human T-cell line		Activity	=	42.1	%	PMID[575365]
NPT5171	Cell Line	Human T-cell line		Activity	=	22.9	%	PMID[575365]
NPT5171	Cell Line	Human T-cell line		Activity	=	19.7	%	PMID[575365]
NPT5171	Cell Line	Human T-cell line		Activity	=	57.4	%	PMID[575365]
NPT5171	Cell Line	Human T-cell line		Activity	=	16.7	%	PMID[575365]
NPT5171	Cell Line	Human T-cell line		Activity	=	16.8	%	PMID[575365]
NPT5171	Cell Line	Human T-cell line		Activity	=	66.5	%	PMID[575365]
NPT5171	Cell Line	Human T-cell line		IC50	=	1100.0	nM	PMID[575365]
NPT5171	Cell Line	Human T-cell line		IC50	=	1000.0	nM	PMID[575365]
NPT2	Others	Unspecified		IC50	=	2000.0	nM	PMID[575361]
NPT2	Others	Unspecified		Ratio	=	1.0	n.a.	PMID[575362]
NPT27	Others	Unspecified		IC50	=	500.0	nM	PMID[575362]
NPT2	Others	Unspecified		IC50	=	2000.0	nM	PMID[575362]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	830.0	nM	PMID[575363]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	1160.0	nM	PMID[575363]

☑ 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 NPC129721 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	365
0.1-0.2	3014
0.2-0.3	18252
0.3-0.4	13392
0.4-0.5	3405
0.5-0.6	2230
0.6-0.7	1438
0.7-0.8	523
0.8-0.85	55
0.85-0.9	21
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9119	High Similarity	NPC248462
0.882	High Similarity	NPC64436
0.8688	High Similarity	NPC158129
0.8528	High Similarity	NPC134586
0.8516	High Similarity	NPC469765
0.8516	High Similarity	NPC25008
0.8516	High Similarity	NPC469786
0.8516	High Similarity	NPC259644
0.8516	High Similarity	NPC73952
0.8516	High Similarity	NPC469760
0.8516	High Similarity	NPC469763
0.8476	Intermediate Similarity	NPC211997
0.8462	Intermediate Similarity	NPC75540
0.8462	Intermediate Similarity	NPC211572
0.8462	Intermediate Similarity	NPC80597
0.8462	Intermediate Similarity	NPC212376
0.8462	Intermediate Similarity	NPC70922
0.84	Intermediate Similarity	NPC104483
0.8385	Intermediate Similarity	NPC474561
0.8385	Intermediate Similarity	NPC49954
0.8365	Intermediate Similarity	NPC255229
0.8365	Intermediate Similarity	NPC81229
0.8313	Intermediate Similarity	NPC282231
0.8291	Intermediate Similarity	NPC469785
0.8274	Intermediate Similarity	NPC159125
0.8272	Intermediate Similarity	NPC160105
0.8267	Intermediate Similarity	NPC150259
0.8261	Intermediate Similarity	NPC194640
0.825	Intermediate Similarity	NPC279918
0.8247	Intermediate Similarity	NPC314372
0.8239	Intermediate Similarity	NPC469762
0.8221	Intermediate Similarity	NPC63751
0.8221	Intermediate Similarity	NPC201700
0.8214	Intermediate Similarity	NPC233936
0.8187	Intermediate Similarity	NPC204565
0.8187	Intermediate Similarity	NPC230869
0.8176	Intermediate Similarity	NPC285469
0.8148	Intermediate Similarity	NPC311276
0.8146	Intermediate Similarity	NPC314102
0.8146	Intermediate Similarity	NPC251722
0.814	Intermediate Similarity	NPC65215
0.814	Intermediate Similarity	NPC173028
0.8117	Intermediate Similarity	NPC190296
0.8095	Intermediate Similarity	NPC133261
0.8081	Intermediate Similarity	NPC317030
0.8072	Intermediate Similarity	NPC314603
0.807	Intermediate Similarity	NPC62510
0.8049	Intermediate Similarity	NPC54988
0.8038	Intermediate Similarity	NPC105818
0.8038	Intermediate Similarity	NPC40070
0.8038	Intermediate Similarity	NPC24678
0.8036	Intermediate Similarity	NPC248454
0.8036	Intermediate Similarity	NPC326575
0.8027	Intermediate Similarity	NPC471313
0.8027	Intermediate Similarity	NPC471311
0.8025	Intermediate Similarity	NPC470111
0.8023	Intermediate Similarity	NPC474707
0.8	Intermediate Similarity	NPC207726
0.8	Intermediate Similarity	NPC20144
0.7989	Intermediate Similarity	NPC95783
0.7976	Intermediate Similarity	NPC24594
0.7976	Intermediate Similarity	NPC472122
0.7976	Intermediate Similarity	NPC121903
0.7975	Intermediate Similarity	NPC16667
0.7955	Intermediate Similarity	NPC474177
0.7929	Intermediate Similarity	NPC59269
0.7929	Intermediate Similarity	NPC151939
0.7927	Intermediate Similarity	NPC40779
0.7927	Intermediate Similarity	NPC478182
0.7922	Intermediate Similarity	NPC73767
0.7917	Intermediate Similarity	NPC469938
0.7914	Intermediate Similarity	NPC131718
0.791	Intermediate Similarity	NPC133366
0.7898	Intermediate Similarity	NPC159856
0.7892	Intermediate Similarity	NPC317430
0.7882	Intermediate Similarity	NPC213468
0.7877	Intermediate Similarity	NPC46358
0.7871	Intermediate Similarity	NPC469780
0.7871	Intermediate Similarity	NPC469761
0.7871	Intermediate Similarity	NPC469783
0.7871	Intermediate Similarity	NPC469768
0.7871	Intermediate Similarity	NPC469767
0.7871	Intermediate Similarity	NPC469784
0.7871	Intermediate Similarity	NPC469779
0.7871	Intermediate Similarity	NPC2949
0.7857	Intermediate Similarity	NPC472123
0.7853	Intermediate Similarity	NPC67056
0.7849	Intermediate Similarity	NPC163055
0.7841	Intermediate Similarity	NPC117244
0.7841	Intermediate Similarity	NPC473763
0.7836	Intermediate Similarity	NPC15840
0.7836	Intermediate Similarity	NPC300688
0.7836	Intermediate Similarity	NPC472105
0.7836	Intermediate Similarity	NPC187827
0.7821	Intermediate Similarity	NPC469766
0.7821	Intermediate Similarity	NPC229332
0.7815	Intermediate Similarity	NPC324611
0.7815	Intermediate Similarity	NPC256893
0.7811	Intermediate Similarity	NPC189812
0.7811	Intermediate Similarity	NPC329688
0.7806	Intermediate Similarity	NPC110126
0.7799	Intermediate Similarity	NPC471957
0.7792	Intermediate Similarity	NPC84911
0.7791	Intermediate Similarity	NPC113626
0.7784	Intermediate Similarity	NPC78020
0.7765	Intermediate Similarity	NPC267885
0.7765	Intermediate Similarity	NPC203754
0.7765	Intermediate Similarity	NPC150048
0.7759	Intermediate Similarity	NPC15102
0.7746	Intermediate Similarity	NPC472109
0.7746	Intermediate Similarity	NPC19679
0.7746	Intermediate Similarity	NPC472110
0.7744	Intermediate Similarity	NPC293487
0.7744	Intermediate Similarity	NPC92796
0.7744	Intermediate Similarity	NPC135141
0.7738	Intermediate Similarity	NPC280548
0.7738	Intermediate Similarity	NPC194411
0.773	Intermediate Similarity	NPC51054
0.7727	Intermediate Similarity	NPC29886
0.7727	Intermediate Similarity	NPC261195
0.7727	Intermediate Similarity	NPC96102
0.7714	Intermediate Similarity	NPC62749
0.7711	Intermediate Similarity	NPC102423
0.7706	Intermediate Similarity	NPC149155
0.7706	Intermediate Similarity	NPC203468
0.7706	Intermediate Similarity	NPC110500
0.7688	Intermediate Similarity	NPC201380
0.7688	Intermediate Similarity	NPC179787
0.7677	Intermediate Similarity	NPC105127
0.7674	Intermediate Similarity	NPC248041
0.7674	Intermediate Similarity	NPC126709
0.7673	Intermediate Similarity	NPC285731
0.7665	Intermediate Similarity	NPC470508
0.7655	Intermediate Similarity	NPC91958
0.7654	Intermediate Similarity	NPC470233
0.7647	Intermediate Similarity	NPC313791
0.764	Intermediate Similarity	NPC37548
0.764	Intermediate Similarity	NPC321911
0.7636	Intermediate Similarity	NPC56765
0.7627	Intermediate Similarity	NPC213629
0.7625	Intermediate Similarity	NPC63545
0.7619	Intermediate Similarity	NPC48564
0.7619	Intermediate Similarity	NPC98187
0.7619	Intermediate Similarity	NPC265605
0.7619	Intermediate Similarity	NPC478183
0.7619	Intermediate Similarity	NPC182570
0.7616	Intermediate Similarity	NPC111275
0.7616	Intermediate Similarity	NPC234987
0.7616	Intermediate Similarity	NPC145885
0.7616	Intermediate Similarity	NPC84827
0.7616	Intermediate Similarity	NPC14113
0.7614	Intermediate Similarity	NPC235684
0.7614	Intermediate Similarity	NPC94752
0.7614	Intermediate Similarity	NPC171171
0.7607	Intermediate Similarity	NPC200214
0.7605	Intermediate Similarity	NPC78375
0.7605	Intermediate Similarity	NPC469541
0.7605	Intermediate Similarity	NPC476446
0.7605	Intermediate Similarity	NPC478184
0.7605	Intermediate Similarity	NPC469813
0.7602	Intermediate Similarity	NPC275305
0.7602	Intermediate Similarity	NPC37423
0.76	Intermediate Similarity	NPC165495
0.7593	Intermediate Similarity	NPC53947
0.7586	Intermediate Similarity	NPC297486
0.7586	Intermediate Similarity	NPC240136
0.7586	Intermediate Similarity	NPC471402
0.7586	Intermediate Similarity	NPC71037
0.758	Intermediate Similarity	NPC315348
0.758	Intermediate Similarity	NPC316811
0.758	Intermediate Similarity	NPC32002
0.7578	Intermediate Similarity	NPC469811
0.7576	Intermediate Similarity	NPC286427
0.7572	Intermediate Similarity	NPC283219
0.7571	Intermediate Similarity	NPC472323
0.7564	Intermediate Similarity	NPC471312
0.7557	Intermediate Similarity	NPC163421
0.7557	Intermediate Similarity	NPC188387
0.7548	Intermediate Similarity	NPC198988
0.7546	Intermediate Similarity	NPC216713
0.7545	Intermediate Similarity	NPC478185
0.7543	Intermediate Similarity	NPC48938
0.7543	Intermediate Similarity	NPC139291
0.7543	Intermediate Similarity	NPC472108
0.7532	Intermediate Similarity	NPC279081
0.7532	Intermediate Similarity	NPC59084
0.7531	Intermediate Similarity	NPC187951
0.753	Intermediate Similarity	NPC41257
0.753	Intermediate Similarity	NPC477591
0.7529	Intermediate Similarity	NPC91895
0.7528	Intermediate Similarity	NPC321708
0.7517	Intermediate Similarity	NPC290094
0.7516	Intermediate Similarity	NPC288838
0.7516	Intermediate Similarity	NPC169433
0.7515	Intermediate Similarity	NPC141353
0.7515	Intermediate Similarity	NPC56233
0.7514	Intermediate Similarity	NPC478077
0.7514	Intermediate Similarity	NPC68354
0.75	Intermediate Similarity	NPC242556
0.75	Intermediate Similarity	NPC228835

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 NPC129721 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	201
0.1-0.2	610
0.2-0.3	980
0.3-0.4	1448
0.4-0.5	2658
0.5-0.6	2088
0.6-0.7	931
0.7-0.8	221
0.8-0.85	12
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8688	High Similarity	NPD5934	Clinical (unspecified phase)
0.8642	High Similarity	NPD6375	Clinical (unspecified phase)
0.8618	High Similarity	NPD4702	Approved
0.8618	High Similarity	NPD4703	Approved
0.8231	Intermediate Similarity	NPD3476	Approved
0.8231	Intermediate Similarity	NPD3475	Approved
0.8171	Intermediate Similarity	NPD4184	Clinical (unspecified phase)
0.8151	Intermediate Similarity	NPD2119	Approved
0.8151	Intermediate Similarity	NPD2118	Approved
0.8141	Intermediate Similarity	NPD4547	Phase 3
0.8133	Intermediate Similarity	NPD5065	Approved
0.8117	Intermediate Similarity	NPD3717	Discontinued
0.8072	Intermediate Similarity	NPD750	Phase 2
0.807	Intermediate Similarity	NPD6610	Clinical (unspecified phase)
0.8067	Intermediate Similarity	NPD3385	Approved
0.8	Intermediate Similarity	NPD4640	Approved
0.8	Intermediate Similarity	NPD4639	Approved
0.8	Intermediate Similarity	NPD4638	Approved
0.7976	Intermediate Similarity	NPD5100	Phase 3
0.7963	Intermediate Similarity	NPD5255	Approved
0.7947	Intermediate Similarity	NPD4030	Approved
0.7947	Intermediate Similarity	NPD4029	Approved
0.7947	Intermediate Similarity	NPD4028	Approved
0.7941	Intermediate Similarity	NPD6595	Phase 3
0.7937	Intermediate Similarity	NPD2012	Clinical (unspecified phase)
0.7935	Intermediate Similarity	NPD1722	Approved
0.7919	Intermediate Similarity	NPD3654	Approved
0.7911	Intermediate Similarity	NPD1661	Suspended
0.7885	Intermediate Similarity	NPD2006	Phase 2
0.7862	Intermediate Similarity	NPD2430	Phase 2
0.7848	Intermediate Similarity	NPD6148	Clinical (unspecified phase)
0.7834	Intermediate Similarity	NPD3813	Approved
0.7829	Intermediate Similarity	NPD3944	Approved
0.7829	Intermediate Similarity	NPD3942	Approved
0.7824	Intermediate Similarity	NPD6203	Clinical (unspecified phase)
0.7806	Intermediate Similarity	NPD786	Approved
0.7784	Intermediate Similarity	NPD2390	Clinical (unspecified phase)
0.7784	Intermediate Similarity	NPD5862	Discovery
0.7765	Intermediate Similarity	NPD749	Clinical (unspecified phase)
0.7765	Intermediate Similarity	NPD7818	Clinical (unspecified phase)
0.7764	Intermediate Similarity	NPD2882	Phase 1
0.775	Intermediate Similarity	NPD3100	Discontinued
0.7746	Intermediate Similarity	NPD5728	Clinical (unspecified phase)
0.7742	Intermediate Similarity	NPD2896	Discontinued
0.7736	Intermediate Similarity	NPD7469	Discontinued
0.7735	Intermediate Similarity	NPD6999	Discontinued
0.7735	Intermediate Similarity	NPD7000	Clinical (unspecified phase)
0.7727	Intermediate Similarity	NPD198	Clinical (unspecified phase)
0.7719	Intermediate Similarity	NPD2144	Approved
0.7716	Intermediate Similarity	NPD2837	Discontinued
0.7706	Intermediate Similarity	NPD482	Approved
0.7702	Intermediate Similarity	NPD2172	Phase 1
0.7697	Intermediate Similarity	NPD6454	Clinical (unspecified phase)
0.7684	Intermediate Similarity	NPD6281	Approved
0.7683	Intermediate Similarity	NPD4326	Phase 2
0.7683	Intermediate Similarity	NPD2581	Approved
0.7683	Intermediate Similarity	NPD2582	Approved
0.7674	Intermediate Similarity	NPD8036	Clinical (unspecified phase)
0.7674	Intermediate Similarity	NPD8037	Clinical (unspecified phase)
0.767	Intermediate Similarity	NPD8431	Approved
0.7665	Intermediate Similarity	NPD5744	Clinical (unspecified phase)
0.7658	Intermediate Similarity	NPD4637	Clinical (unspecified phase)
0.7654	Intermediate Similarity	NPD6158	Phase 2
0.7654	Intermediate Similarity	NPD3262	Approved
0.7654	Intermediate Similarity	NPD6476	Clinical (unspecified phase)
0.7651	Intermediate Similarity	NPD5315	Discontinued
0.7644	Intermediate Similarity	NPD2094	Phase 2
0.7644	Intermediate Similarity	NPD2095	Phase 2
0.7644	Intermediate Similarity	NPD2092	Phase 2
0.7627	Intermediate Similarity	NPD8110	Clinical (unspecified phase)
0.7622	Intermediate Similarity	NPD6026	Approved
0.7619	Intermediate Similarity	NPD270	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD271	Approved
0.7619	Intermediate Similarity	NPD268	Approved
0.7616	Intermediate Similarity	NPD8122	Approved
0.7616	Intermediate Similarity	NPD8123	Approved
0.7611	Intermediate Similarity	NPD7944	Discontinued
0.761	Intermediate Similarity	NPD751	Clinical (unspecified phase)
0.7609	Intermediate Similarity	NPD5721	Clinical (unspecified phase)
0.76	Intermediate Similarity	NPD2091	Phase 2
0.76	Intermediate Similarity	NPD2096	Phase 2
0.7598	Intermediate Similarity	NPD3404	Approved
0.7586	Intermediate Similarity	NPD3038	Discontinued
0.758	Intermediate Similarity	NPD2069	Approved
0.758	Intermediate Similarity	NPD2070	Approved
0.758	Intermediate Similarity	NPD2071	Approved
0.758	Intermediate Similarity	NPD2075	Approved
0.758	Intermediate Similarity	NPD2072	Approved
0.758	Intermediate Similarity	NPD2068	Approved
0.758	Intermediate Similarity	NPD2073	Approved
0.758	Intermediate Similarity	NPD2074	Approved
0.7576	Intermediate Similarity	NPD5541	Clinical (unspecified phase)
0.7574	Intermediate Similarity	NPD5069	Clinical (unspecified phase)
0.7574	Intermediate Similarity	NPD4779	Clinical (unspecified phase)
0.7572	Intermediate Similarity	NPD4076	Approved
0.7572	Intermediate Similarity	NPD4079	Approved
0.7564	Intermediate Similarity	NPD6554	Approved
0.7564	Intermediate Similarity	NPD45	Approved
0.756	Intermediate Similarity	NPD926	Approved
0.756	Intermediate Similarity	NPD925	Approved
0.7557	Intermediate Similarity	NPD7424	Clinical (unspecified phase)
0.755	Intermediate Similarity	NPD991	Phase 2
0.755	Intermediate Similarity	NPD992	Clinical (unspecified phase)
0.7531	Intermediate Similarity	NPD1183	Approved
0.7531	Intermediate Similarity	NPD4374	Clinical (unspecified phase)
0.7529	Intermediate Similarity	NPD1325	Approved
0.7529	Intermediate Similarity	NPD1326	Approved
0.7515	Intermediate Similarity	NPD2580	Discontinued
0.7514	Intermediate Similarity	NPD4181	Approved
0.7514	Intermediate Similarity	NPD3505	Approved
0.7514	Intermediate Similarity	NPD3506	Approved
0.75	Intermediate Similarity	NPD1095	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD3323	Discontinued
0.75	Intermediate Similarity	NPD4957	Phase 2
0.7485	Intermediate Similarity	NPD2511	Approved
0.7484	Intermediate Similarity	NPD5020	Approved
0.7471	Intermediate Similarity	NPD2641	Approved
0.7471	Intermediate Similarity	NPD2640	Approved
0.7459	Intermediate Similarity	NPD5575	Clinical (unspecified phase)
0.7459	Intermediate Similarity	NPD7903	Clinical (unspecified phase)
0.7458	Intermediate Similarity	NPD5555	Phase 1
0.7458	Intermediate Similarity	NPD6344	Clinical (unspecified phase)
0.7456	Intermediate Similarity	NPD4550	Clinical (unspecified phase)
0.7456	Intermediate Similarity	NPD2720	Phase 1
0.7456	Intermediate Similarity	NPD2719	Clinical (unspecified phase)
0.7446	Intermediate Similarity	NPD6661	Clinical (unspecified phase)
0.7443	Intermediate Similarity	NPD2391	Clinical (unspecified phase)
0.744	Intermediate Similarity	NPD8026	Phase 1
0.7433	Intermediate Similarity	NPD5426	Phase 3
0.7433	Intermediate Similarity	NPD6987	Phase 1
0.743	Intermediate Similarity	NPD6965	Clinical (unspecified phase)
0.7429	Intermediate Similarity	NPD6452	Discontinued
0.7418	Intermediate Similarity	NPD4602	Approved
0.7414	Intermediate Similarity	NPD1272	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD7666	Phase 3
0.7407	Intermediate Similarity	NPD7665	Phase 2
0.7407	Intermediate Similarity	NPD1683	Approved
0.7403	Intermediate Similarity	NPD715	Phase 3
0.7399	Intermediate Similarity	NPD4128	Approved
0.7396	Intermediate Similarity	NPD8129	Discovery
0.7386	Intermediate Similarity	NPD4383	Clinical (unspecified phase)
0.738	Intermediate Similarity	NPD4886	Phase 2
0.7378	Intermediate Similarity	NPD4462	Approved
0.7378	Intermediate Similarity	NPD4463	Approved
0.7374	Intermediate Similarity	NPD2383	Phase 1
0.7371	Intermediate Similarity	NPD8386	Phase 2
0.7368	Intermediate Similarity	NPD9583	Approved
0.7349	Intermediate Similarity	NPD2809	Approved
0.7348	Intermediate Similarity	NPD2336	Approved
0.7346	Intermediate Similarity	NPD5995	Clinical (unspecified phase)
0.7341	Intermediate Similarity	NPD966	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD2007	Clinical (unspecified phase)
0.7322	Intermediate Similarity	NPD7619	Phase 3
0.7322	Intermediate Similarity	NPD4999	Phase 3
0.7322	Intermediate Similarity	NPD4998	Phase 3
0.7322	Intermediate Similarity	NPD4427	Phase 2
0.7322	Intermediate Similarity	NPD7618	Phase 3
0.732	Intermediate Similarity	NPD9284	Approved
0.7312	Intermediate Similarity	NPD3943	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD1649	Discontinued
0.7308	Intermediate Similarity	NPD1995	Approved
0.7308	Intermediate Similarity	NPD1993	Approved
0.7308	Intermediate Similarity	NPD1994	Approved
0.7308	Intermediate Similarity	NPD4615	Phase 2
0.7303	Intermediate Similarity	NPD5892	Approved
0.7302	Intermediate Similarity	NPD7001	Phase 3
0.7284	Intermediate Similarity	NPD1918	Clinical (unspecified phase)
0.7283	Intermediate Similarity	NPD3610	Approved
0.7283	Intermediate Similarity	NPD3116	Approved
0.7283	Intermediate Similarity	NPD1078	Clinical (unspecified phase)
0.7283	Intermediate Similarity	NPD3117	Approved
0.7283	Intermediate Similarity	NPD3609	Approved
0.7278	Intermediate Similarity	NPD1404	Approved
0.7278	Intermediate Similarity	NPD3002	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD3486	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD1403	Approved
0.7268	Intermediate Similarity	NPD802	Phase 2
0.7267	Intermediate Similarity	NPD1592	Phase 3
0.7267	Intermediate Similarity	NPD5021	Discontinued
0.7262	Intermediate Similarity	NPD2865	Clinical (unspecified phase)
0.7258	Intermediate Similarity	NPD7621	Clinical (unspecified phase)
0.7257	Intermediate Similarity	NPD4075	Phase 2
0.7251	Intermediate Similarity	NPD1568	Clinical (unspecified phase)
0.7246	Intermediate Similarity	NPD2165	Phase 1
0.7243	Intermediate Similarity	NPD7948	Phase 1
0.7241	Intermediate Similarity	NPD4112	Clinical (unspecified phase)
0.7237	Intermediate Similarity	NPD9357	Approved
0.7235	Intermediate Similarity	NPD2385	Clinical (unspecified phase)
0.7235	Intermediate Similarity	NPD1853	Clinical (unspecified phase)
0.7233	Intermediate Similarity	NPD200	Phase 2
0.7233	Intermediate Similarity	NPD201	Phase 2
0.7232	Intermediate Similarity	NPD8464	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD4047	Discontinued
0.7219	Intermediate Similarity	NPD748	Clinical (unspecified phase)
0.7216	Intermediate Similarity	NPD7111	Discontinued
0.7216	Intermediate Similarity	NPD5751	Clinical (unspecified phase)
0.7213	Intermediate Similarity	NPD5505	Discontinued
0.7212	Intermediate Similarity	NPD3576	Approved
0.7212	Intermediate Similarity	NPD3575	Approved
0.7211	Intermediate Similarity	NPD6732	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