NPASS Compound

Structure

CID22133 OpenBabel06191715352D 31 35 0 0 1 0 0 0 0 0999 V2000 1.8836 -3.1612 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3932 -5.4195 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6901 2.9585 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5626 2.4546 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6904 -1.9823 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6896 1.0083 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7903 -3.5659 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4889 -2.6391 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7437 -3.7682 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0006 1.9512 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8445 1.4636 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3788 -0.9740 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5337 0.4871 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3785 0.0010 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6893 -0.0005 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8453 -1.4626 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0003 -0.9750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8448 -0.4881 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5355 -2.4367 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.0451 -4.6951 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5352 -1.4621 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8453 1.4632 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8448 0.4880 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5340 1.4627 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6898 1.9507 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6901 -0.9745 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6899 0.0005 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8451 0.4876 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.9985 -4.8974 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4003 1.9623 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 20 1 0 0 0 0 3 25 1 0 0 0 0 4 25 1 0 0 0 0 5 26 1 0 0 0 0 7 8 1 0 0 0 0 7 9 2 0 0 0 0 8 19 1 0 0 0 0 9 20 1 0 0 0 0 10 11 1 0 0 0 0 10 22 1 0 0 0 0 11 23 1 0 0 0 0 12 14 1 0 0 0 0 12 21 1 0 0 0 0 13 15 1 0 0 0 0 13 24 1 0 0 0 0 14 27 1 0 0 0 0 15 28 1 0 0 0 0 16 17 1 0 0 0 0 16 26 1 0 0 0 0 18 28 1 0 0 0 0 18 29 1 0 0 0 0 19 1 1 1 0 0 0 19 21 1 0 0 0 0 20 30 2 0 0 0 0 21 26 1 6 0 0 0 22 25 1 0 0 0 0 22 28 1 6 0 0 0 23 27 1 1 0 0 0 23 29 1 0 0 0 0 24 25 1 0 0 0 0 24 31 1 6 0 0 0 26 27 1 6 0 0 0 27 6 1 1 0 0 0 28 29 1 1 0 0 0 29 17 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	426.35
Volume:	479.665
LogP:	6.046
LogD:	4.785
LogS:	-5.321
# Rotatable Bonds:	4
TPSA:	37.3
# H-Bond Aceptor:	2
# H-Bond Donor:	1
# Rings:	5
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.493
Synthetic Accessibility Score:	5.492
Fsp3:	0.897
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.021
MDCK Permeability:	2.0573774236254394e-05
Pgp-inhibitor:	0.329
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.941
30% Bioavailability (F30%):	0.984

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.072
Plasma Protein Binding (PPB):	97.02222442626953%
Volume Distribution (VD):	1.187
Pgp-substrate:	1.884730339050293%

ADMET: Metabolism

CYP1A2-inhibitor:	0.031
CYP1A2-substrate:	0.47
CYP2C19-inhibitor:	0.106
CYP2C19-substrate:	0.91
CYP2C9-inhibitor:	0.243
CYP2C9-substrate:	0.109
CYP2D6-inhibitor:	0.071
CYP2D6-substrate:	0.364
CYP3A4-inhibitor:	0.876
CYP3A4-substrate:	0.778

ADMET: Excretion

Clearance (CL):	7.01
Half-life (T1/2):	0.213

ADMET: Toxicity

hERG Blockers:	0.084
Human Hepatotoxicity (H-HT):	0.474
Drug-inuced Liver Injury (DILI):	0.037
AMES Toxicity:	0.006
Rat Oral Acute Toxicity:	0.321
Maximum Recommended Daily Dose:	0.956
Skin Sensitization:	0.964
Carcinogencity:	0.193
Eye Corrosion:	0.949
Eye Irritation:	0.507
Respiratory Toxicity:	0.977

Download Data

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

Natural Product: NPC22133

Natural Product ID:	NPC22133
*Common Name:**	WNTCMDLOMSFFPE-GXBJFGSMSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	WNTCMDLOMSFFPE-GXBJFGSMSA-N
Standard InCHI:	InChI=1S/C29H46O2/c1-19(8-7-9-20(2)30)21-12-14-27(6)23-11-10-22-25(3,4)24(31)13-15-28(22)18-29(23,28)17-16-26(21,27)5/h7,9,19,21-24,31H,8,10-18H2,1-6H3/b9-7+/t19-,21-,22+,23+,24+,26-,27+,28-,29+/m1/s1
SMILES:	CC(=O)/C=C/C[C@H]([C@H]1CC[C@@]2([C@]1(C)CC[C@@]13[C@H]2CC[C@@H]2[C@]3(C1)CC[C@@H](C2(C)C)O)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL523455
PubChem CID:	21626061
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0002321] Cycloartanols and derivatives

*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
NPO7811	Scleronephthya pallida	Species	Nephtheidae	Eukaryota	n.a.	n.a.	n.a.	PMID[10075773]
NPO2717	Vatica cinerea	Species	Dipterocarpaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12608862]
NPO10376	Arcyria denudata	Species	Trichiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[16933891]
NPO6249	Garcinia mangostana	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18464091]
NPO6249	Garcinia mangostana	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18558747]
NPO6249	Garcinia mangostana	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19299148]
NPO6249	Garcinia mangostana	Species	Clusiaceae	Eukaryota	stem bark	Pangradin village, Jasinga, West Java, Indonesia	2005-AUG	PMID[19839614]
NPO6249	Garcinia mangostana	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20817450]
NPO6249	Garcinia mangostana	Species	Clusiaceae	Eukaryota	n.a.	pericarp	n.a.	PMID[24555285]
NPO6249	Garcinia mangostana	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24717154]
NPO41067	Trigona minor	Species	Apidae	Eukaryota	n.a.	n.a.	n.a.	PMID[28783356]
NPO6249	Garcinia mangostana	Species	Clusiaceae	Eukaryota	fruit hulls	Madras, Tamil Nadu, India	1993-MAR	PMID[9213587]
NPO6249	Garcinia mangostana	Species	Clusiaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO6249	Garcinia mangostana	Species	Clusiaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO6249	Garcinia mangostana	Species	Clusiaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO6249	Garcinia mangostana	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO10849	Eucalyptus camaldulensis	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO10849	Eucalyptus camaldulensis	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10391	Dolomiaea souliei	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6249	Garcinia mangostana	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10391	Dolomiaea souliei	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO10849	Eucalyptus camaldulensis	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8560	Aplidium tabascum	Species	Polyclinidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8927	Poria selecta	Species	Coccinellidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9741	Actinopyga agassizi	Species	Holothuriidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2717	Vatica cinerea	Species	Dipterocarpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3707	Chromatium okenii	Species	Chromatiaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO7811	Scleronephthya pallida	Species	Nephtheidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6249	Garcinia mangostana	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27924	Serpocaulon triseriale	Species	Polypodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10391	Dolomiaea souliei	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4064	Halimodendron halodendron	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25216	Senecio vellereus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10376	Arcyria denudata	Species	Trichiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9717	Wibelia divaricata	Species	Davalliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8354	Aster bellidiastrum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12600	Trametes cinnabarina	Species	Coriolaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3449	Lonicera hypoleuca	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10221	Streptomyces alboniger	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO10056	Nicotiana sylvestris	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7534	Leptogorgia sarmentosa	Species	Gorgoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24931	Myelochroa aurulenta	Species	Parmeliaceae	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	1
Others	3

Activity Type	# Activity
Cell Line	1
Organism	2
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT461	Cell Line	PANC-1	Homo sapiens	PC50	=	16.4	uM	PMID[527137]
NPT27	Others	Unspecified		CC50	=	12700.0	nM	PMID[527136]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	IC50	=	5900.0	nM	PMID[527136]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	Inhibition	=	21.0	%	PMID[527136]

☑ 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 NPC22133 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	168
0.1-0.2	1321
0.2-0.3	6504
0.3-0.4	16447
0.4-0.5	6757
0.5-0.6	5848
0.6-0.7	4245
0.7-0.8	1302
0.8-0.85	72
0.85-0.9	31
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9277	High Similarity	NPC89747
0.8916	High Similarity	NPC33913
0.8875	High Similarity	NPC65897
0.8875	High Similarity	NPC85346
0.8875	High Similarity	NPC302041
0.8851	High Similarity	NPC74296
0.8851	High Similarity	NPC110923
0.8851	High Similarity	NPC272746
0.8795	High Similarity	NPC82623
0.8795	High Similarity	NPC134481
0.875	High Similarity	NPC476304
0.875	High Similarity	NPC12722
0.8736	High Similarity	NPC126993
0.869	High Similarity	NPC472265
0.8652	High Similarity	NPC476186
0.8642	High Similarity	NPC138621
0.8642	High Similarity	NPC312328
0.8642	High Similarity	NPC244385
0.8642	High Similarity	NPC6978
0.8642	High Similarity	NPC285761
0.8642	High Similarity	NPC167037
0.8625	High Similarity	NPC237460
0.8588	High Similarity	NPC76518
0.8571	High Similarity	NPC113978
0.8554	High Similarity	NPC6434
0.8537	High Similarity	NPC80530
0.8537	High Similarity	NPC273410
0.8523	High Similarity	NPC85173
0.85	High Similarity	NPC70982
0.85	High Similarity	NPC230704
0.8462	Intermediate Similarity	NPC195366
0.8462	Intermediate Similarity	NPC114743
0.8452	Intermediate Similarity	NPC218616
0.8452	Intermediate Similarity	NPC296701
0.8434	Intermediate Similarity	NPC322313
0.8434	Intermediate Similarity	NPC236237
0.8434	Intermediate Similarity	NPC13554
0.8434	Intermediate Similarity	NPC102253
0.8409	Intermediate Similarity	NPC262858
0.8409	Intermediate Similarity	NPC472240
0.8395	Intermediate Similarity	NPC129165
0.8395	Intermediate Similarity	NPC134330
0.8395	Intermediate Similarity	NPC189883
0.8391	Intermediate Similarity	NPC475740
0.8391	Intermediate Similarity	NPC93778
0.8391	Intermediate Similarity	NPC141292
0.8391	Intermediate Similarity	NPC475772
0.8391	Intermediate Similarity	NPC58063
0.8375	Intermediate Similarity	NPC254509
0.8375	Intermediate Similarity	NPC196358
0.8375	Intermediate Similarity	NPC145552
0.8375	Intermediate Similarity	NPC5046
0.8375	Intermediate Similarity	NPC49168
0.8372	Intermediate Similarity	NPC470574
0.8353	Intermediate Similarity	NPC477818
0.8353	Intermediate Similarity	NPC193870
0.8353	Intermediate Similarity	NPC470558
0.8353	Intermediate Similarity	NPC141941
0.8315	Intermediate Similarity	NPC191684
0.8313	Intermediate Similarity	NPC1319
0.8295	Intermediate Similarity	NPC292491
0.8295	Intermediate Similarity	NPC474677
0.8295	Intermediate Similarity	NPC471722
0.8295	Intermediate Similarity	NPC328539
0.8295	Intermediate Similarity	NPC193360
0.8295	Intermediate Similarity	NPC310752
0.8293	Intermediate Similarity	NPC34019
0.8293	Intermediate Similarity	NPC331618
0.8293	Intermediate Similarity	NPC257191
0.8293	Intermediate Similarity	NPC214570
0.8276	Intermediate Similarity	NPC31564
0.8276	Intermediate Similarity	NPC269058
0.8276	Intermediate Similarity	NPC145879
0.8276	Intermediate Similarity	NPC72133
0.8276	Intermediate Similarity	NPC474732
0.8276	Intermediate Similarity	NPC474733
0.8276	Intermediate Similarity	NPC474778
0.8276	Intermediate Similarity	NPC71520
0.8272	Intermediate Similarity	NPC141071
0.8272	Intermediate Similarity	NPC257347
0.8272	Intermediate Similarity	NPC200243
0.8272	Intermediate Similarity	NPC471723
0.8272	Intermediate Similarity	NPC103822
0.8261	Intermediate Similarity	NPC160056
0.8256	Intermediate Similarity	NPC127606
0.8256	Intermediate Similarity	NPC475798
0.8256	Intermediate Similarity	NPC85774
0.8256	Intermediate Similarity	NPC214043
0.825	Intermediate Similarity	NPC195489
0.8242	Intermediate Similarity	NPC201725
0.8222	Intermediate Similarity	NPC475806
0.8214	Intermediate Similarity	NPC236112
0.8202	Intermediate Similarity	NPC146554
0.8202	Intermediate Similarity	NPC128496
0.8202	Intermediate Similarity	NPC309603
0.8202	Intermediate Similarity	NPC31985
0.8202	Intermediate Similarity	NPC1015
0.8202	Intermediate Similarity	NPC473999
0.8202	Intermediate Similarity	NPC86319
0.8202	Intermediate Similarity	NPC275740
0.8202	Intermediate Similarity	NPC119416
0.8193	Intermediate Similarity	NPC11908
0.8193	Intermediate Similarity	NPC472342
0.8193	Intermediate Similarity	NPC275910
0.8172	Intermediate Similarity	NPC108078
0.8171	Intermediate Similarity	NPC46160
0.8171	Intermediate Similarity	NPC107059
0.8171	Intermediate Similarity	NPC202642
0.8171	Intermediate Similarity	NPC300324
0.8171	Intermediate Similarity	NPC321016
0.8171	Intermediate Similarity	NPC470362
0.8171	Intermediate Similarity	NPC113733
0.8171	Intermediate Similarity	NPC321381
0.8171	Intermediate Similarity	NPC73875
0.8171	Intermediate Similarity	NPC240604
0.8152	Intermediate Similarity	NPC476174
0.8148	Intermediate Similarity	NPC22134
0.814	Intermediate Similarity	NPC139206
0.814	Intermediate Similarity	NPC110778
0.814	Intermediate Similarity	NPC207013
0.8132	Intermediate Similarity	NPC475255
0.8125	Intermediate Similarity	NPC111234
0.8118	Intermediate Similarity	NPC474531
0.8111	Intermediate Similarity	NPC48010
0.8095	Intermediate Similarity	NPC30986
0.8095	Intermediate Similarity	NPC209430
0.8095	Intermediate Similarity	NPC472463
0.809	Intermediate Similarity	NPC67872
0.809	Intermediate Similarity	NPC131470
0.809	Intermediate Similarity	NPC143767
0.809	Intermediate Similarity	NPC471724
0.8085	Intermediate Similarity	NPC103051
0.8072	Intermediate Similarity	NPC198968
0.8072	Intermediate Similarity	NPC155986
0.8072	Intermediate Similarity	NPC318495
0.8072	Intermediate Similarity	NPC470428
0.8068	Intermediate Similarity	NPC474970
0.8068	Intermediate Similarity	NPC139724
0.8068	Intermediate Similarity	NPC475022
0.8068	Intermediate Similarity	NPC222613
0.8068	Intermediate Similarity	NPC6605
0.8068	Intermediate Similarity	NPC94462
0.8068	Intermediate Similarity	NPC118648
0.8049	Intermediate Similarity	NPC136188
0.8049	Intermediate Similarity	NPC134847
0.8049	Intermediate Similarity	NPC288035
0.8049	Intermediate Similarity	NPC185536
0.8049	Intermediate Similarity	NPC285893
0.8049	Intermediate Similarity	NPC118508
0.8049	Intermediate Similarity	NPC3403
0.8049	Intermediate Similarity	NPC28657
0.8049	Intermediate Similarity	NPC212879
0.8049	Intermediate Similarity	NPC304309
0.8049	Intermediate Similarity	NPC230301
0.8049	Intermediate Similarity	NPC121744
0.8049	Intermediate Similarity	NPC240235
0.8049	Intermediate Similarity	NPC162742
0.8049	Intermediate Similarity	NPC231256
0.8049	Intermediate Similarity	NPC104387
0.8049	Intermediate Similarity	NPC178383
0.8049	Intermediate Similarity	NPC322353
0.8049	Intermediate Similarity	NPC22105
0.8046	Intermediate Similarity	NPC470077
0.8046	Intermediate Similarity	NPC473246
0.8046	Intermediate Similarity	NPC59453
0.8046	Intermediate Similarity	NPC474493
0.8046	Intermediate Similarity	NPC221758
0.8046	Intermediate Similarity	NPC209802
0.8043	Intermediate Similarity	NPC209662
0.8043	Intermediate Similarity	NPC471207
0.8043	Intermediate Similarity	NPC299100
0.8043	Intermediate Similarity	NPC196485
0.8043	Intermediate Similarity	NPC8993
0.8043	Intermediate Similarity	NPC111015
0.8043	Intermediate Similarity	NPC245972
0.8025	Intermediate Similarity	NPC182717
0.8023	Intermediate Similarity	NPC49964
0.8023	Intermediate Similarity	NPC30166
0.8023	Intermediate Similarity	NPC248886
0.8023	Intermediate Similarity	NPC87489
0.8023	Intermediate Similarity	NPC470049
0.8022	Intermediate Similarity	NPC168027
0.8022	Intermediate Similarity	NPC212948
0.8022	Intermediate Similarity	NPC185936
0.8022	Intermediate Similarity	NPC275671
0.8022	Intermediate Similarity	NPC473998
0.8	Intermediate Similarity	NPC164840
0.8	Intermediate Similarity	NPC234193
0.8	Intermediate Similarity	NPC45296
0.8	Intermediate Similarity	NPC122116
0.8	Intermediate Similarity	NPC26959
0.8	Intermediate Similarity	NPC186688
0.8	Intermediate Similarity	NPC241290
0.8	Intermediate Similarity	NPC209944
0.8	Intermediate Similarity	NPC268406
0.7978	Intermediate Similarity	NPC186145
0.7978	Intermediate Similarity	NPC474657
0.7978	Intermediate Similarity	NPC474684
0.7978	Intermediate Similarity	NPC142361
0.7976	Intermediate Similarity	NPC148977

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 NPC22133 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	148
0.1-0.2	1575
0.2-0.3	4598
0.3-0.4	2071
0.4-0.5	350
0.5-0.6	134
0.6-0.7	174
0.7-0.8	96
0.8-0.85	4
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8636	High Similarity	NPD6079	Approved
0.8434	Intermediate Similarity	NPD7525	Registered
0.8409	Intermediate Similarity	NPD5328	Approved
0.8276	Intermediate Similarity	NPD3618	Phase 1
0.8095	Intermediate Similarity	NPD4195	Approved
0.8065	Intermediate Similarity	NPD5222	Approved
0.8065	Intermediate Similarity	NPD5221	Approved
0.8065	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.8049	Intermediate Similarity	NPD6942	Approved
0.8049	Intermediate Similarity	NPD7339	Approved
0.8046	Intermediate Similarity	NPD4786	Approved
0.7979	Intermediate Similarity	NPD5173	Approved
0.7935	Intermediate Similarity	NPD4202	Approved
0.7841	Intermediate Similarity	NPD3665	Phase 1
0.7841	Intermediate Similarity	NPD3133	Approved
0.7841	Intermediate Similarity	NPD3666	Approved
0.7816	Intermediate Similarity	NPD3667	Approved
0.7812	Intermediate Similarity	NPD5285	Approved
0.7812	Intermediate Similarity	NPD5286	Approved
0.7812	Intermediate Similarity	NPD4696	Approved
0.7738	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7732	Intermediate Similarity	NPD5223	Approved
0.7708	Intermediate Similarity	NPD5290	Discontinued
0.7684	Intermediate Similarity	NPD4697	Phase 3
0.7674	Intermediate Similarity	NPD7645	Phase 2
0.7653	Intermediate Similarity	NPD5225	Approved
0.7653	Intermediate Similarity	NPD5226	Approved
0.7653	Intermediate Similarity	NPD5224	Approved
0.7653	Intermediate Similarity	NPD5211	Phase 2
0.7653	Intermediate Similarity	NPD4633	Approved
0.7634	Intermediate Similarity	NPD7515	Phase 2
0.7604	Intermediate Similarity	NPD4755	Approved
0.7576	Intermediate Similarity	NPD5175	Approved
0.7576	Intermediate Similarity	NPD5174	Approved
0.7556	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7528	Intermediate Similarity	NPD4788	Approved
0.7526	Intermediate Similarity	NPD7638	Approved
0.75	Intermediate Similarity	NPD6926	Approved
0.75	Intermediate Similarity	NPD6924	Approved
0.75	Intermediate Similarity	NPD5141	Approved
0.7473	Intermediate Similarity	NPD5279	Phase 3
0.747	Intermediate Similarity	NPD7151	Approved
0.747	Intermediate Similarity	NPD7150	Approved
0.747	Intermediate Similarity	NPD7152	Approved
0.7451	Intermediate Similarity	NPD6899	Approved
0.7451	Intermediate Similarity	NPD6881	Approved
0.7449	Intermediate Similarity	NPD7640	Approved
0.7449	Intermediate Similarity	NPD7639	Approved
0.7449	Intermediate Similarity	NPD4700	Approved
0.7419	Intermediate Similarity	NPD4753	Phase 2
0.7416	Intermediate Similarity	NPD4223	Phase 3
0.7416	Intermediate Similarity	NPD4221	Approved
0.7396	Intermediate Similarity	NPD5210	Approved
0.7396	Intermediate Similarity	NPD4629	Approved
0.7363	Intermediate Similarity	NPD5329	Approved
0.7353	Intermediate Similarity	NPD5697	Approved
0.7349	Intermediate Similarity	NPD7144	Approved
0.7349	Intermediate Similarity	NPD7143	Approved
0.7326	Intermediate Similarity	NPD6933	Approved
0.7308	Intermediate Similarity	NPD7102	Approved
0.7308	Intermediate Similarity	NPD7290	Approved
0.7308	Intermediate Similarity	NPD6883	Approved
0.7294	Intermediate Similarity	NPD4784	Approved
0.7294	Intermediate Similarity	NPD4785	Approved
0.7292	Intermediate Similarity	NPD7748	Approved
0.7283	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7283	Intermediate Similarity	NPD5690	Phase 2
0.7282	Intermediate Similarity	NPD6011	Approved
0.7282	Intermediate Similarity	NPD4730	Approved
0.7282	Intermediate Similarity	NPD5168	Approved
0.7282	Intermediate Similarity	NPD4729	Approved
0.7262	Intermediate Similarity	NPD4809	Clinical (unspecified phase)
0.7262	Intermediate Similarity	NPD4808	Clinical (unspecified phase)
0.7262	Intermediate Similarity	NPD4243	Approved
0.7255	Intermediate Similarity	NPD7128	Approved
0.7255	Intermediate Similarity	NPD6675	Approved
0.7255	Intermediate Similarity	NPD6402	Approved
0.7255	Intermediate Similarity	NPD5739	Approved
0.7253	Intermediate Similarity	NPD4197	Approved
0.7238	Intermediate Similarity	NPD6617	Approved
0.7238	Intermediate Similarity	NPD6869	Approved
0.7238	Intermediate Similarity	NPD6650	Approved
0.7238	Intermediate Similarity	NPD6847	Approved
0.7238	Intermediate Similarity	NPD6649	Approved
0.7238	Intermediate Similarity	NPD8130	Phase 1
0.7229	Intermediate Similarity	NPD6923	Approved
0.7229	Intermediate Similarity	NPD6922	Approved
0.7228	Intermediate Similarity	NPD4754	Approved
0.7212	Intermediate Similarity	NPD6012	Approved
0.7212	Intermediate Similarity	NPD6013	Approved
0.7212	Intermediate Similarity	NPD6014	Approved
0.7188	Intermediate Similarity	NPD6399	Phase 3
0.717	Intermediate Similarity	NPD8297	Approved
0.717	Intermediate Similarity	NPD6882	Approved
0.7143	Intermediate Similarity	NPD5169	Approved
0.7143	Intermediate Similarity	NPD5247	Approved
0.7143	Intermediate Similarity	NPD5251	Approved
0.7143	Intermediate Similarity	NPD4634	Approved
0.7143	Intermediate Similarity	NPD5134	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD5135	Approved
0.7143	Intermediate Similarity	NPD5248	Approved
0.7143	Intermediate Similarity	NPD5249	Phase 3
0.7143	Intermediate Similarity	NPD5250	Approved
0.7128	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD7320	Approved
0.7115	Intermediate Similarity	NPD5128	Approved
0.7111	Intermediate Similarity	NPD6902	Approved
0.7097	Intermediate Similarity	NPD6684	Approved
0.7097	Intermediate Similarity	NPD5205	Approved
0.7097	Intermediate Similarity	NPD5330	Approved
0.7097	Intermediate Similarity	NPD4693	Phase 3
0.7097	Intermediate Similarity	NPD6409	Approved
0.7097	Intermediate Similarity	NPD7521	Approved
0.7097	Intermediate Similarity	NPD7334	Approved
0.7097	Intermediate Similarity	NPD4690	Approved
0.7097	Intermediate Similarity	NPD7146	Approved
0.7097	Intermediate Similarity	NPD4688	Approved
0.7097	Intermediate Similarity	NPD4689	Approved
0.7097	Intermediate Similarity	NPD4138	Approved
0.7087	Intermediate Similarity	NPD4768	Approved
0.7087	Intermediate Similarity	NPD4767	Approved
0.7079	Intermediate Similarity	NPD6929	Approved
0.7075	Intermediate Similarity	NPD5215	Approved
0.7075	Intermediate Similarity	NPD5127	Approved
0.7075	Intermediate Similarity	NPD5217	Approved
0.7075	Intermediate Similarity	NPD5216	Approved
0.7071	Intermediate Similarity	NPD6084	Phase 2
0.7071	Intermediate Similarity	NPD6083	Phase 2
0.7071	Intermediate Similarity	NPD7902	Approved
0.7065	Intermediate Similarity	NPD3668	Phase 3
0.7064	Intermediate Similarity	NPD7115	Discovery
0.7048	Intermediate Similarity	NPD6372	Approved
0.7048	Intermediate Similarity	NPD6373	Approved
0.7045	Intermediate Similarity	NPD6932	Approved
0.7041	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7024	Intermediate Similarity	NPD3699	Clinical (unspecified phase)
0.7024	Intermediate Similarity	NPD4267	Clinical (unspecified phase)
0.7024	Intermediate Similarity	NPD3700	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD4751	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD5701	Approved
0.7	Intermediate Similarity	NPD4748	Discontinued
0.7	Intermediate Similarity	NPD6931	Approved
0.7	Intermediate Similarity	NPD6930	Phase 2
0.7	Intermediate Similarity	NPD7509	Discontinued
0.6972	Remote Similarity	NPD6868	Approved
0.6966	Remote Similarity	NPD3617	Approved
0.6966	Remote Similarity	NPD7145	Approved
0.6947	Remote Similarity	NPD6903	Approved
0.6947	Remote Similarity	NPD6672	Approved
0.6947	Remote Similarity	NPD5737	Approved
0.6944	Remote Similarity	NPD4632	Approved
0.6932	Remote Similarity	NPD6117	Approved
0.6916	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6915	Remote Similarity	NPD5280	Approved
0.6915	Remote Similarity	NPD4694	Approved
0.6907	Remote Similarity	NPD8035	Phase 2
0.6907	Remote Similarity	NPD8034	Phase 2
0.6897	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6881	Remote Similarity	NPD5167	Approved
0.6854	Remote Similarity	NPD5776	Phase 2
0.6854	Remote Similarity	NPD6116	Phase 1
0.6854	Remote Similarity	NPD6925	Approved
0.6847	Remote Similarity	NPD6335	Approved
0.6842	Remote Similarity	NPD7604	Phase 2
0.6818	Remote Similarity	NPD4190	Phase 3
0.6818	Remote Similarity	NPD3703	Phase 2
0.6818	Remote Similarity	NPD5275	Approved
0.6813	Remote Similarity	NPD4695	Discontinued
0.6813	Remote Similarity	NPD7514	Phase 3
0.6796	Remote Similarity	NPD7632	Discontinued
0.6786	Remote Similarity	NPD7100	Approved
0.6786	Remote Similarity	NPD7101	Approved
0.6778	Remote Similarity	NPD6118	Approved
0.6778	Remote Similarity	NPD6114	Approved
0.6778	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6778	Remote Similarity	NPD6115	Approved
0.6778	Remote Similarity	NPD6697	Approved
0.6774	Remote Similarity	NPD6695	Phase 3
0.6768	Remote Similarity	NPD7900	Approved
0.6768	Remote Similarity	NPD6001	Approved
0.6768	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD6009	Approved
0.6757	Remote Similarity	NPD6317	Approved
0.6744	Remote Similarity	NPD4789	Approved
0.6744	Remote Similarity	NPD4244	Approved
0.6744	Remote Similarity	NPD4747	Approved
0.6744	Remote Similarity	NPD4245	Approved
0.6744	Remote Similarity	NPD4691	Approved
0.6744	Remote Similarity	NPD4787	Phase 1
0.6737	Remote Similarity	NPD4623	Approved
0.6737	Remote Similarity	NPD4519	Discontinued
0.6735	Remote Similarity	NPD5281	Approved
0.6735	Remote Similarity	NPD5284	Approved
0.6726	Remote Similarity	NPD6054	Approved
0.6706	Remote Similarity	NPD5360	Phase 3
0.6706	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.6705	Remote Similarity	NPD4058	Approved
0.6703	Remote Similarity	NPD6683	Phase 2
0.6702	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.67	Remote Similarity	NPD5695	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