NPASS Compound

Structure

CID43063 OpenBabel06191715372D 28 33 0 0 1 0 0 0 0 0999 V2000 -0.0796 3.7687 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4975 2.3721 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6875 2.6652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6128 1.8607 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8066 1.3953 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6174 2.6652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6122 4.6523 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8050 3.2567 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8064 4.1873 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6112 2.7912 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4186 3.2565 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4167 0.4651 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6875 1.0546 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2226 1.8599 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6128 2.7916 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.4183 4.1869 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0006 2.7915 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0005 1.8607 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.4173 1.3950 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.6111 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.0823 1.8599 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8067 3.2570 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.6112 1.8604 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8056 1.3953 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.2843 4.6870 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0121 1.8599 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.6174 1.0546 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 2 23 1 0 0 0 0 3 6 2 0 0 0 0 3 14 1 0 0 0 0 4 5 1 0 0 0 0 4 15 1 0 0 0 0 5 18 1 0 0 0 0 6 21 1 0 0 0 0 7 9 1 0 0 0 0 7 16 1 0 0 0 0 8 10 1 0 0 0 0 8 17 1 0 0 0 0 9 22 1 0 0 0 0 10 23 1 0 0 0 0 11 15 1 0 0 0 0 11 16 1 0 0 0 0 12 19 1 0 0 0 0 12 20 1 0 0 0 0 13 14 2 0 0 0 0 13 27 1 0 0 0 0 14 19 1 0 0 0 0 15 22 1 1 0 0 0 16 25 1 1 0 0 0 17 18 1 0 0 0 0 17 22 1 6 0 0 0 18 24 1 1 0 0 0 19 23 1 6 0 0 0 20 24 1 1 0 0 0 20 28 1 0 0 0 0 21 26 2 0 0 0 0 21 27 1 0 0 0 0 22 1 1 6 0 0 0 23 24 1 6 0 0 0 24 28 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	384.23
Volume:	399.573
LogP:	4.176
LogD:	3.501
LogS:	-5.416
# Rotatable Bonds:	1
TPSA:	62.97
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	6
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.735
Synthetic Accessibility Score:	5.072
Fsp3:	0.792
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:	-4.899
MDCK Permeability:	1.10412402136717e-05
Pgp-inhibitor:	0.051
Pgp-substrate:	0.999
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.856
30% Bioavailability (F30%):	0.979

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.093
Plasma Protein Binding (PPB):	94.32657623291016%
Volume Distribution (VD):	1.697
Pgp-substrate:	4.182643890380859%

ADMET: Metabolism

CYP1A2-inhibitor:	0.127
CYP1A2-substrate:	0.562
CYP2C19-inhibitor:	0.203
CYP2C19-substrate:	0.668
CYP2C9-inhibitor:	0.356
CYP2C9-substrate:	0.059
CYP2D6-inhibitor:	0.116
CYP2D6-substrate:	0.643
CYP3A4-inhibitor:	0.663
CYP3A4-substrate:	0.417

ADMET: Excretion

Clearance (CL):	16.184
Half-life (T1/2):	0.155

ADMET: Toxicity

hERG Blockers:	0.946
Human Hepatotoxicity (H-HT):	0.914
Drug-inuced Liver Injury (DILI):	0.678
AMES Toxicity:	0.01
Rat Oral Acute Toxicity:	0.952
Maximum Recommended Daily Dose:	0.967
Skin Sensitization:	0.677
Carcinogencity:	0.392
Eye Corrosion:	0.387
Eye Irritation:	0.433
Respiratory Toxicity:	0.967

Download Data

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

Natural Product: NPC43063

Natural Product ID:	NPC43063
*Common Name:**	ATLJNLYIJOCWJE-GBXHWQOESA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	ATLJNLYIJOCWJE-GBXHWQOESA-N
Standard InCHI:	InChI=1S/C24H32O4/c1-22-9-7-16(25)11-15(22)4-5-18-17(22)8-10-23(2)19(12-20-24(18,23)28-20)14-3-6-21(26)27-13-14/h3,6,13,15-20,25H,4-5,7-12H2,1-2H3/t15-,16-,17+,18-,19-,20-,22+,23-,24-/m1/s1
SMILES:	C[C@]12CC[C@H](C[C@H]1CC[C@@H]1[C@@H]2CC[C@]2(C)[C@H](C[C@@H]3[C@]12O3)c1ccc(=O)oc1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2069026
PubChem CID:	70684536
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001125] Steroid lactones [CHEMONTID:0001557] Bufanolides 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
NPO12012	Saururus cernuus	Species	Saururaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/S0040-4039(01)99818-1]
NPO19205	Buxus sempervirens	Species	Buxaceae	Eukaryota	roots	n.a.	n.a.	PMID[10346940]
NPO12012	Saururus cernuus	Species	Saururaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11421725]
NPO12012	Saururus cernuus	Species	Saururaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15165135]
NPO3983	Piper futokadsura	Species	Piperaceae	Eukaryota	n.a.	aerial part	n.a.	PMID[15635246]
NPO223	Rhaponticum carthamoides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15730237]
NPO664	Potentilla multifida	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17504571]
NPO9576	Bufo bufo	Species	Bufonidae	Eukaryota	n.a.	n.a.	n.a.	PMID[21185919]
NPO11885	Dysoxylum lenticellatum	Species	Meliaceae	Eukaryota	n.a.	twig	n.a.	PMID[21954912]
NPO11885	Dysoxylum lenticellatum	Species	Meliaceae	Eukaryota	twigs and leaves	Yunnan Province, China	2008-OCT	PMID[21954912]
NPO11885	Dysoxylum lenticellatum	Species	Meliaceae	Eukaryota	n.a.	leaf	n.a.	PMID[21954912]
NPO10672	Vitex megapotamica	Species	Lamiaceae	Eukaryota	n.a.	leaf	n.a.	PMID[22708620]
NPO19205	Buxus sempervirens	Species	Buxaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26722868]
NPO18636	Cupressus macrocarpa	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32223924]
NPO223	Rhaponticum carthamoides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO12012	Saururus cernuus	Species	Saururaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO19205	Buxus sempervirens	Species	Buxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO19205	Buxus sempervirens	Species	Buxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10672	Vitex megapotamica	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18636	Cupressus macrocarpa	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12012	Saururus cernuus	Species	Saururaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO223	Rhaponticum carthamoides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19205	Buxus sempervirens	Species	Buxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO12012	Saururus cernuus	Species	Saururaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO223	Rhaponticum carthamoides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO9576	Bufo bufo	Species	Bufonidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO18636	Cupressus macrocarpa	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11885	Dysoxylum lenticellatum	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO664	Potentilla multifida	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7884	Centaurea amara	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11515	Streptomyces plumbeus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO26231	Vicia villosa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2917	Artemisia oranensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7543	Haplopappus venetus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12250	Strychnos fendleri	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4797	Gavia immer	Species	Gaviidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3983	Piper futokadsura	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10672	Vitex megapotamica	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12952	Cabucala madagascariensis	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10043	Phebalium ozothamnoides	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO223	Rhaponticum carthamoides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5177	Lecanora conizaeoides	Species	Lecanoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6887	Lytanthus salicinus	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO12735	Halimeda macroloba	Species	Halimedaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9398	Cortinarius rubellus	Species	Cortinariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9576	Bufo bufo	Species	Bufonidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19205	Buxus sempervirens	Species	Buxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2498	Kochia trichophylla	Species	Chenopodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12012	Saururus cernuus	Species	Saururaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21463	Aruncus dioicus	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6011	Pleurotus citrinopileatus	Species	Pleurotaceae	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

Activity Type	# Activity
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified		IC50	=	8.3	ug.mL-1	PMID[488221]
NPT2	Others	Unspecified		IC50	=	43.0	ug.mL-1	PMID[488221]

☑ 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 NPC43063 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	363
0.1-0.2	1475
0.2-0.3	2753
0.3-0.4	5262
0.4-0.5	11157
0.5-0.6	10162
0.6-0.7	9749
0.7-0.8	1520
0.8-0.85	186
0.85-0.9	24
0.9-0.95	35
0.95-1	11

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC79298
0.9703	High Similarity	NPC103491
0.9694	High Similarity	NPC171014
0.95	High Similarity	NPC295843
0.9423	High Similarity	NPC171126
0.9412	High Similarity	NPC75389
0.94	High Similarity	NPC165969
0.9314	High Similarity	NPC304276
0.9314	High Similarity	NPC137462
0.9314	High Similarity	NPC275060
0.9159	High Similarity	NPC157380
0.9159	High Similarity	NPC185287
0.9143	High Similarity	NPC44537
0.9135	High Similarity	NPC16270
0.9135	High Similarity	NPC12795
0.9074	High Similarity	NPC16701
0.9048	High Similarity	NPC183603
0.8991	High Similarity	NPC278681
0.8991	High Similarity	NPC213761
0.8991	High Similarity	NPC35171
0.8909	High Similarity	NPC112936
0.8879	High Similarity	NPC154815
0.8879	High Similarity	NPC73050
0.8879	High Similarity	NPC241977
0.8785	High Similarity	NPC247760
0.875	High Similarity	NPC189863
0.8661	High Similarity	NPC312481
0.8571	High Similarity	NPC257610
0.8571	High Similarity	NPC114939
0.8571	High Similarity	NPC145074
0.8571	High Similarity	NPC266570
0.8571	High Similarity	NPC41123
0.8559	High Similarity	NPC146786
0.8558	High Similarity	NPC297617
0.8544	High Similarity	NPC268829
0.8544	High Similarity	NPC222875
0.8544	High Similarity	NPC25177
0.8544	High Similarity	NPC247701
0.8544	High Similarity	NPC295110
0.8509	High Similarity	NPC6193
0.85	High Similarity	NPC201725
0.8431	Intermediate Similarity	NPC231751
0.8407	Intermediate Similarity	NPC184555
0.8381	Intermediate Similarity	NPC189588
0.8381	Intermediate Similarity	NPC10232
0.8381	Intermediate Similarity	NPC196471
0.8381	Intermediate Similarity	NPC97487
0.8381	Intermediate Similarity	NPC160583
0.8381	Intermediate Similarity	NPC187302
0.8362	Intermediate Similarity	NPC159499
0.835	Intermediate Similarity	NPC92275
0.835	Intermediate Similarity	NPC181147
0.8348	Intermediate Similarity	NPC55602
0.8333	Intermediate Similarity	NPC299654
0.8333	Intermediate Similarity	NPC16967
0.8224	Intermediate Similarity	NPC186668
0.8224	Intermediate Similarity	NPC119855
0.8224	Intermediate Similarity	NPC220217
0.8218	Intermediate Similarity	NPC476304
0.8214	Intermediate Similarity	NPC113425
0.8214	Intermediate Similarity	NPC232564
0.8208	Intermediate Similarity	NPC472821
0.8208	Intermediate Similarity	NPC112009
0.82	Intermediate Similarity	NPC302280
0.8198	Intermediate Similarity	NPC122056
0.819	Intermediate Similarity	NPC194028
0.819	Intermediate Similarity	NPC168319
0.8182	Intermediate Similarity	NPC284162
0.8182	Intermediate Similarity	NPC255401
0.8173	Intermediate Similarity	NPC218107
0.8173	Intermediate Similarity	NPC108368
0.8173	Intermediate Similarity	NPC278673
0.8173	Intermediate Similarity	NPC57079
0.8165	Intermediate Similarity	NPC475030
0.8158	Intermediate Similarity	NPC264954
0.8155	Intermediate Similarity	NPC190713
0.8137	Intermediate Similarity	NPC476186
0.8137	Intermediate Similarity	NPC191521
0.8131	Intermediate Similarity	NPC472822
0.8131	Intermediate Similarity	NPC200861
0.8119	Intermediate Similarity	NPC74296
0.8119	Intermediate Similarity	NPC110923
0.8095	Intermediate Similarity	NPC472826
0.8095	Intermediate Similarity	NPC201406
0.8095	Intermediate Similarity	NPC251680
0.8087	Intermediate Similarity	NPC474370
0.8077	Intermediate Similarity	NPC141401
0.8077	Intermediate Similarity	NPC99726
0.8039	Intermediate Similarity	NPC205034
0.8039	Intermediate Similarity	NPC214697
0.8039	Intermediate Similarity	NPC38232
0.8039	Intermediate Similarity	NPC162615
0.8039	Intermediate Similarity	NPC152778
0.8037	Intermediate Similarity	NPC180204
0.802	Intermediate Similarity	NPC310479
0.8018	Intermediate Similarity	NPC262083
0.8018	Intermediate Similarity	NPC474315
0.8018	Intermediate Similarity	NPC470076
0.8018	Intermediate Similarity	NPC471484
0.8	Intermediate Similarity	NPC473879
0.8	Intermediate Similarity	NPC98868
0.8	Intermediate Similarity	NPC221414
0.7982	Intermediate Similarity	NPC167606
0.7982	Intermediate Similarity	NPC290693
0.7982	Intermediate Similarity	NPC470492
0.7982	Intermediate Similarity	NPC140055
0.7982	Intermediate Similarity	NPC286528
0.7982	Intermediate Similarity	NPC20302
0.7981	Intermediate Similarity	NPC195366
0.7981	Intermediate Similarity	NPC114743
0.7966	Intermediate Similarity	NPC233041
0.7963	Intermediate Similarity	NPC272632
0.7949	Intermediate Similarity	NPC153700
0.7949	Intermediate Similarity	NPC88326
0.7946	Intermediate Similarity	NPC475970
0.7946	Intermediate Similarity	NPC476163
0.7944	Intermediate Similarity	NPC155332
0.7944	Intermediate Similarity	NPC32577
0.7944	Intermediate Similarity	NPC114540
0.7941	Intermediate Similarity	NPC329842
0.7941	Intermediate Similarity	NPC212948
0.7941	Intermediate Similarity	NPC177641
0.7928	Intermediate Similarity	NPC238850
0.7925	Intermediate Similarity	NPC227865
0.7925	Intermediate Similarity	NPC290802
0.7921	Intermediate Similarity	NPC472240
0.7921	Intermediate Similarity	NPC473647
0.7921	Intermediate Similarity	NPC262858
0.7913	Intermediate Similarity	NPC50774
0.7913	Intermediate Similarity	NPC709
0.7905	Intermediate Similarity	NPC210337
0.7905	Intermediate Similarity	NPC51499
0.7899	Intermediate Similarity	NPC179261
0.789	Intermediate Similarity	NPC472818
0.789	Intermediate Similarity	NPC81630
0.7885	Intermediate Similarity	NPC474909
0.7885	Intermediate Similarity	NPC472441
0.7879	Intermediate Similarity	NPC474013
0.787	Intermediate Similarity	NPC45897
0.787	Intermediate Similarity	NPC183570
0.787	Intermediate Similarity	NPC85742
0.7857	Intermediate Similarity	NPC470558
0.7845	Intermediate Similarity	NPC153085
0.7845	Intermediate Similarity	NPC268326
0.7843	Intermediate Similarity	NPC221111
0.7843	Intermediate Similarity	NPC78973
0.7843	Intermediate Similarity	NPC280149
0.7843	Intermediate Similarity	NPC182136
0.7843	Intermediate Similarity	NPC273199
0.783	Intermediate Similarity	NPC275086
0.783	Intermediate Similarity	NPC325229
0.7826	Intermediate Similarity	NPC183580
0.7826	Intermediate Similarity	NPC312824
0.7826	Intermediate Similarity	NPC470493
0.7826	Intermediate Similarity	NPC243065
0.7822	Intermediate Similarity	NPC93411
0.7822	Intermediate Similarity	NPC471952
0.7818	Intermediate Similarity	NPC472820
0.7815	Intermediate Similarity	NPC8374
0.781	Intermediate Similarity	NPC301534
0.781	Intermediate Similarity	NPC250757
0.781	Intermediate Similarity	NPC253115
0.781	Intermediate Similarity	NPC88009
0.781	Intermediate Similarity	NPC473153
0.781	Intermediate Similarity	NPC304899
0.7807	Intermediate Similarity	NPC69576
0.7807	Intermediate Similarity	NPC31354
0.7807	Intermediate Similarity	NPC147912
0.7807	Intermediate Similarity	NPC67259
0.7807	Intermediate Similarity	NPC216665
0.7807	Intermediate Similarity	NPC471633
0.7807	Intermediate Similarity	NPC84949
0.78	Intermediate Similarity	NPC474970
0.78	Intermediate Similarity	NPC131813
0.7798	Intermediate Similarity	NPC472819
0.7788	Intermediate Similarity	NPC279410
0.7788	Intermediate Similarity	NPC105490
0.7788	Intermediate Similarity	NPC119562
0.7788	Intermediate Similarity	NPC150228
0.7788	Intermediate Similarity	NPC214005
0.7778	Intermediate Similarity	NPC470077
0.7778	Intermediate Similarity	NPC306951
0.7778	Intermediate Similarity	NPC475038
0.7778	Intermediate Similarity	NPC109195
0.7767	Intermediate Similarity	NPC234335
0.7757	Intermediate Similarity	NPC230546
0.7757	Intermediate Similarity	NPC266955
0.7757	Intermediate Similarity	NPC473510
0.7748	Intermediate Similarity	NPC472825
0.7745	Intermediate Similarity	NPC177141
0.7745	Intermediate Similarity	NPC82876
0.7745	Intermediate Similarity	NPC146554
0.7742	Intermediate Similarity	NPC248703
0.7739	Intermediate Similarity	NPC5311
0.7739	Intermediate Similarity	NPC193382
0.7739	Intermediate Similarity	NPC310341
0.7739	Intermediate Similarity	NPC470075
0.7739	Intermediate Similarity	NPC199428
0.7739	Intermediate Similarity	NPC99620
0.7736	Intermediate Similarity	NPC253826

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 NPC43063 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	321
0.1-0.2	910
0.2-0.3	1572
0.3-0.4	2596
0.4-0.5	2261
0.5-0.6	1108
0.6-0.7	353
0.7-0.8	23
0.8-0.85	5
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8174	Intermediate Similarity	NPD7503	Approved
0.8173	Intermediate Similarity	NPD7638	Approved
0.8095	Intermediate Similarity	NPD7640	Approved
0.8095	Intermediate Similarity	NPD7639	Approved
0.7982	Intermediate Similarity	NPD7115	Discovery
0.7607	Intermediate Similarity	NPD7327	Approved
0.7607	Intermediate Similarity	NPD7328	Approved
0.7589	Intermediate Similarity	NPD6881	Approved
0.7589	Intermediate Similarity	NPD6899	Approved
0.7573	Intermediate Similarity	NPD6051	Approved
0.7542	Intermediate Similarity	NPD7516	Approved
0.75	Intermediate Similarity	NPD5697	Approved
0.7479	Intermediate Similarity	NPD8294	Approved
0.7479	Intermediate Similarity	NPD8377	Approved
0.7456	Intermediate Similarity	NPD7290	Approved
0.7456	Intermediate Similarity	NPD7102	Approved
0.7456	Intermediate Similarity	NPD6883	Approved
0.7455	Intermediate Similarity	NPD7632	Discontinued
0.7434	Intermediate Similarity	NPD6011	Approved
0.7417	Intermediate Similarity	NPD8379	Approved
0.7417	Intermediate Similarity	NPD8378	Approved
0.7417	Intermediate Similarity	NPD8033	Approved
0.7417	Intermediate Similarity	NPD8296	Approved
0.7417	Intermediate Similarity	NPD8380	Approved
0.7417	Intermediate Similarity	NPD8335	Approved
0.7411	Intermediate Similarity	NPD6675	Approved
0.7411	Intermediate Similarity	NPD7128	Approved
0.7411	Intermediate Similarity	NPD6402	Approved
0.7411	Intermediate Similarity	NPD5739	Approved
0.7391	Intermediate Similarity	NPD6869	Approved
0.7391	Intermediate Similarity	NPD8130	Phase 1
0.7391	Intermediate Similarity	NPD6847	Approved
0.7391	Intermediate Similarity	NPD6650	Approved
0.7391	Intermediate Similarity	NPD6649	Approved
0.7391	Intermediate Similarity	NPD6617	Approved
0.7374	Intermediate Similarity	NPD7525	Registered
0.7368	Intermediate Similarity	NPD6012	Approved
0.7368	Intermediate Similarity	NPD6013	Approved
0.7368	Intermediate Similarity	NPD6014	Approved
0.7328	Intermediate Similarity	NPD6882	Approved
0.7328	Intermediate Similarity	NPD8297	Approved
0.7281	Intermediate Similarity	NPD7320	Approved
0.7248	Intermediate Similarity	NPD6084	Phase 2
0.7248	Intermediate Similarity	NPD6083	Phase 2
0.7217	Intermediate Similarity	NPD6372	Approved
0.7217	Intermediate Similarity	NPD6373	Approved
0.7193	Intermediate Similarity	NPD5701	Approved
0.7182	Intermediate Similarity	NPD4225	Approved
0.7177	Intermediate Similarity	NPD7507	Approved
0.7143	Intermediate Similarity	NPD5211	Phase 2
0.7143	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.713	Intermediate Similarity	NPD7748	Approved
0.7117	Intermediate Similarity	NPD5285	Approved
0.7117	Intermediate Similarity	NPD5286	Approved
0.7117	Intermediate Similarity	NPD4696	Approved
0.7103	Intermediate Similarity	NPD7515	Phase 2
0.7103	Intermediate Similarity	NPD6079	Approved
0.71	Intermediate Similarity	NPD4195	Approved
0.7094	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7064	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7054	Intermediate Similarity	NPD5223	Approved
0.7037	Intermediate Similarity	NPD4202	Approved
0.7034	Intermediate Similarity	NPD6053	Discontinued
0.7025	Intermediate Similarity	NPD6335	Approved
0.7019	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD5141	Approved
0.7008	Intermediate Similarity	NPD7319	Approved
0.6991	Remote Similarity	NPD4633	Approved
0.6991	Remote Similarity	NPD5225	Approved
0.6991	Remote Similarity	NPD5224	Approved
0.6991	Remote Similarity	NPD5226	Approved
0.6975	Remote Similarity	NPD4632	Approved
0.6967	Remote Similarity	NPD7101	Approved
0.6967	Remote Similarity	NPD7100	Approved
0.6964	Remote Similarity	NPD6648	Approved
0.6957	Remote Similarity	NPD6008	Approved
0.6952	Remote Similarity	NPD6409	Approved
0.6952	Remote Similarity	NPD7146	Approved
0.6952	Remote Similarity	NPD7521	Approved
0.6952	Remote Similarity	NPD5330	Approved
0.6952	Remote Similarity	NPD6684	Approved
0.6952	Remote Similarity	NPD7334	Approved
0.6944	Remote Similarity	NPD8035	Phase 2
0.6944	Remote Similarity	NPD8034	Phase 2
0.6944	Remote Similarity	NPD7637	Suspended
0.6944	Remote Similarity	NPD5281	Approved
0.6944	Remote Similarity	NPD5284	Approved
0.6944	Remote Similarity	NPD5693	Phase 1
0.6942	Remote Similarity	NPD6317	Approved
0.6937	Remote Similarity	NPD7902	Approved
0.6937	Remote Similarity	NPD4755	Approved
0.693	Remote Similarity	NPD5175	Approved
0.693	Remote Similarity	NPD5174	Approved
0.6916	Remote Similarity	NPD5328	Approved
0.6909	Remote Similarity	NPD5695	Phase 3
0.6903	Remote Similarity	NPD5344	Discontinued
0.6885	Remote Similarity	NPD6313	Approved
0.6885	Remote Similarity	NPD6314	Approved
0.6881	Remote Similarity	NPD6399	Phase 3
0.688	Remote Similarity	NPD7604	Phase 2
0.6875	Remote Similarity	NPD5696	Approved
0.686	Remote Similarity	NPD6274	Approved
0.6847	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6847	Remote Similarity	NPD5222	Approved
0.6847	Remote Similarity	NPD5221	Approved
0.6827	Remote Similarity	NPD6695	Phase 3
0.6827	Remote Similarity	NPD4788	Approved
0.6822	Remote Similarity	NPD6903	Approved
0.6814	Remote Similarity	NPD4700	Approved
0.6803	Remote Similarity	NPD6009	Approved
0.68	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6797	Remote Similarity	NPD7736	Approved
0.6792	Remote Similarity	NPD3618	Phase 1
0.6789	Remote Similarity	NPD5694	Approved
0.6789	Remote Similarity	NPD6050	Approved
0.6786	Remote Similarity	NPD5173	Approved
0.678	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD6319	Approved
0.6768	Remote Similarity	NPD6926	Approved
0.6768	Remote Similarity	NPD6924	Approved
0.6765	Remote Similarity	NPD7645	Phase 2
0.6762	Remote Similarity	NPD3666	Approved
0.6762	Remote Similarity	NPD3665	Phase 1
0.6762	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6762	Remote Similarity	NPD3133	Approved
0.6759	Remote Similarity	NPD6904	Approved
0.6759	Remote Similarity	NPD6673	Approved
0.6759	Remote Similarity	NPD6080	Approved
0.6759	Remote Similarity	NPD4753	Phase 2
0.6757	Remote Similarity	NPD5210	Approved
0.6757	Remote Similarity	NPD4629	Approved
0.6754	Remote Similarity	NPD4159	Approved
0.6731	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6729	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6721	Remote Similarity	NPD6868	Approved
0.672	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.672	Remote Similarity	NPD5983	Phase 2
0.67	Remote Similarity	NPD6942	Approved
0.67	Remote Similarity	NPD7339	Approved
0.6697	Remote Similarity	NPD5692	Phase 3
0.6697	Remote Similarity	NPD5207	Approved
0.6697	Remote Similarity	NPD5785	Approved
0.6695	Remote Similarity	NPD4730	Approved
0.6695	Remote Similarity	NPD4729	Approved
0.6693	Remote Similarity	NPD7492	Approved
0.6667	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6672	Approved
0.6667	Remote Similarity	NPD5737	Approved
0.6667	Remote Similarity	NPD7900	Approved
0.6667	Remote Similarity	NPD6001	Approved
0.6641	Remote Similarity	NPD6336	Discontinued
0.6641	Remote Similarity	NPD6616	Approved
0.664	Remote Similarity	NPD6054	Approved
0.6638	Remote Similarity	NPD4754	Approved
0.6634	Remote Similarity	NPD6933	Approved
0.6604	Remote Similarity	NPD4786	Approved
0.66	Remote Similarity	NPD4785	Approved
0.66	Remote Similarity	NPD4784	Approved
0.6596	Remote Similarity	NPD7236	Approved
0.6589	Remote Similarity	NPD7078	Approved
0.6587	Remote Similarity	NPD6908	Approved
0.6587	Remote Similarity	NPD6909	Approved
0.6583	Remote Similarity	NPD5247	Approved
0.6583	Remote Similarity	NPD5249	Phase 3
0.6583	Remote Similarity	NPD5250	Approved
0.6583	Remote Similarity	NPD5251	Approved
0.6583	Remote Similarity	NPD5135	Approved
0.6583	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6583	Remote Similarity	NPD4634	Approved
0.6583	Remote Similarity	NPD5169	Approved
0.6583	Remote Similarity	NPD5248	Approved
0.6583	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6574	Remote Similarity	NPD3573	Approved
0.6574	Remote Similarity	NPD7750	Discontinued
0.6574	Remote Similarity	NPD7524	Approved
0.6571	Remote Similarity	NPD4221	Approved
0.6571	Remote Similarity	NPD4223	Phase 3
0.6566	Remote Similarity	NPD7152	Approved
0.6566	Remote Similarity	NPD7151	Approved
0.6566	Remote Similarity	NPD4243	Approved
0.6566	Remote Similarity	NPD7150	Approved
0.6555	Remote Similarity	NPD6686	Approved
0.6555	Remote Similarity	NPD5128	Approved
0.6549	Remote Similarity	NPD4697	Phase 3
0.6545	Remote Similarity	NPD7838	Discovery
0.6542	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6542	Remote Similarity	NPD5329	Approved
0.6542	Remote Similarity	NPD1694	Approved
0.6538	Remote Similarity	NPD7514	Phase 3
0.6538	Remote Similarity	NPD6930	Phase 2
0.6538	Remote Similarity	NPD6931	Approved
0.6535	Remote Similarity	NPD6370	Approved
0.6529	Remote Similarity	NPD5216	Approved
0.6529	Remote Similarity	NPD5127	Approved
0.6529	Remote Similarity	NPD5215	Approved
0.6529	Remote Similarity	NPD5217	Approved
0.6525	Remote Similarity	NPD4768	Approved
0.6525	Remote Similarity	NPD4767	Approved
0.6514	Remote Similarity	NPD5208	Approved
0.6505	Remote Similarity	NPD7322	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