NPASS Compound

Structure

CID52968 OpenBabel06191715392D 26 31 0 0 1 0 0 0 0 0999 V2000 -1.9319 -0.5176 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1533 -1.0580 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1001 -1.8862 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7818 -2.3778 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0591 -1.8771 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8978 -0.7765 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7071 0.7071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3801 1.1554 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9511 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9619 0.8119 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6730 0.4483 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5388 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6238 -2.1249 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.4194 -2.3611 0.0000 C 0 0 2 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 1.0000 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.6049 -0.0694 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3461 0.8966 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9511 -1.3090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.0000 -1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5791 -3.3482 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8040 -3.9801 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.5138 -3.7036 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.6035 -0.1217 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.1847 1.4412 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 6 2 0 0 0 0 1 11 1 0 0 0 0 2 3 2 0 0 0 0 3 15 1 0 0 0 0 4 5 2 0 0 0 0 6 18 1 0 0 0 0 7 11 1 0 0 0 0 8 11 2 0 0 0 0 8 19 1 0 0 0 0 9 12 1 0 0 0 0 10 25 1 0 0 0 0 10 26 1 0 0 0 0 12 2 1 1 0 0 0 12 20 1 0 0 0 0 13 4 1 6 0 0 0 13 15 1 0 0 0 0 13 20 1 0 0 0 0 14 5 1 6 0 0 0 14 16 1 0 0 0 0 14 21 1 0 0 0 0 15 22 1 1 0 0 0 16 7 1 1 0 0 0 16 17 1 0 0 0 0 17 9 1 6 0 0 0 17 21 1 0 0 0 0 18 19 2 0 0 0 0 18 25 1 0 0 0 0 19 26 1 0 0 0 0 20 21 1 0 0 0 0 22 23 2 0 0 0 0 22 24 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	350.15
Volume:	357.072
LogP:	5.013
LogD:	4.598
LogS:	-3.86
# Rotatable Bonds:	3
TPSA:	55.76
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	6
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.845
Synthetic Accessibility Score:	4.644
Fsp3:	0.5
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:	-4.917
MDCK Permeability:	3.130791083094664e-05
Pgp-inhibitor:	0.002
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.05
30% Bioavailability (F30%):	0.94

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.373
Plasma Protein Binding (PPB):	95.08611297607422%
Volume Distribution (VD):	0.544
Pgp-substrate:	7.2369842529296875%

ADMET: Metabolism

CYP1A2-inhibitor:	0.893
CYP1A2-substrate:	0.267
CYP2C19-inhibitor:	0.373
CYP2C19-substrate:	0.311
CYP2C9-inhibitor:	0.66
CYP2C9-substrate:	0.398
CYP2D6-inhibitor:	0.719
CYP2D6-substrate:	0.374
CYP3A4-inhibitor:	0.901
CYP3A4-substrate:	0.188

ADMET: Excretion

Clearance (CL):	13.118
Half-life (T1/2):	0.719

ADMET: Toxicity

hERG Blockers:	0.056
Human Hepatotoxicity (H-HT):	0.757
Drug-inuced Liver Injury (DILI):	0.178
AMES Toxicity:	0.014
Rat Oral Acute Toxicity:	0.639
Maximum Recommended Daily Dose:	0.884
Skin Sensitization:	0.888
Carcinogencity:	0.691
Eye Corrosion:	0.012
Eye Irritation:	0.104
Respiratory Toxicity:	0.968

Download Data

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

Natural Product: NPC52968

Natural Product ID:	NPC52968
*Common Name:**	Tsangibeilin B
IUPAC Name:	n.a.
Synonyms:	Tsangibeilin B
Standard InCHIKey:	DXINWPCQBUXMER-STJBOKOVSA-N
Standard InCHI:	InChI=1S/C22H22O4/c23-22(24)15-3-2-12-9-17-16(14-5-4-13(15)20(12)21(14)17)7-11-1-6-18-19(8-11)26-10-25-18/h1-6,8,12-17,20-21H,7,9-10H2,(H,23,24)/t12-,13+,14-,15-,16-,17+,20-,21-/m1/s1
SMILES:	c1cc2c(cc1C[C@@H]1[C@H]3C=C[C@H]4[C@@H](C=C[C@@H]5C[C@@H]1[C@@H]3[C@@H]45)C(=O)O)OCO2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1821986
PubChem CID:	54671629
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000296] Benzodioxoles

*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
NPO4331	Plakortis lita	Species	Plakinidae	Eukaryota	n.a.	Palauan	n.a.	PMID[10479343]
NPO4331	Plakortis lita	Species	Plakinidae	Eukaryota	n.a.	Okinawan	n.a.	PMID[11277756]
NPO25126	Sarcophyton latum	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16724849]
NPO25126	Sarcophyton latum	Species	Orchidaceae	Eukaryota	n.a.	Hainan soft coral	n.a.	PMID[16724849]
NPO9339	Beilschmiedia tsangii	Species	Lauraceae	Eukaryota	roots	Mudan, Pingtung County, Taiwan	2009-APR	PMID[21846089]
NPO9339	Beilschmiedia tsangii	Species	Lauraceae	Eukaryota	n.a.	root	n.a.	PMID[21846089]
NPO33452	beilschmiedia cryptocaryoides	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23320609]
NPO8247	Austrobaileya scandens	Species	Austrobaileyaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27214307]
NPO2861	Pentaceraster regulus	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[28981263]
NPO4331	Plakortis lita	Species	Plakinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[9722494]
NPO569	Micromelum integerrimum	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO569	Micromelum integerrimum	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5844	Schlumbergera truncata	Species	Cactaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO569	Micromelum integerrimum	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO9215	Papaver glaucum	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25126	Sarcophyton latum	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27884	Sphacelaria arctica	Species	Sphacelariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9339	Beilschmiedia tsangii	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4888	Salvia divaricata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6053	Veronica intercedens	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2861	Pentaceraster regulus	Species	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO4331	Plakortis lita	Species	Plakinidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO772	Bosistoa floydii	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO345	Quercus laurifolia	Species	Fagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5844	Schlumbergera truncata	Species	Cactaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6791	Malva rotundifolia	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6305	Euphorbia jaxartica	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO134	Cassia artemisioides	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7401	Centaurea dealbata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO569	Micromelum integerrimum	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3331	Hedysarum sachalinense	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5582	Inocybe aeruginascens	Species	Inocybaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1462	Amomum sulcatum	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8247	Austrobaileya scandens	Species	Austrobaileyaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	3
MIC	4
Others	1

Activity Type	# Activity
Cell Line	1
Individual Protein	2
NON-MOLECULAR	2
Organism	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT270	Individual Protein	Nitric oxide synthase, inducible	Mus musculus	Emax	=	96.07	%	PMID[475906]
NPT270	Individual Protein	Nitric oxide synthase, inducible	Mus musculus	IC50	=	42300.0	nM	PMID[475906]
NPT839	Cell Line	L6	Rattus norvegicus	IC50	=	21500.0	nM	PMID[475907]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	8200.0	nM	PMID[475907]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	=	50.0	ug.mL-1	PMID[475907]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	MIC	>	50.0	ug.mL-1	PMID[475907]
NPT3163	Organism	Acinetobacter calcoaceticus	Acinetobacter calcoaceticus	MIC	>	50.0	ug.mL-1	PMID[475907]

☑ 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 NPC52968 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	334
0.1-0.2	1421
0.2-0.3	3025
0.3-0.4	8534
0.4-0.5	11221
0.5-0.6	8173
0.6-0.7	8916
0.7-0.8	1017
0.8-0.85	46
0.85-0.9	6
0.9-0.95	1
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC231719
0.9774	High Similarity	NPC323601
0.942	High Similarity	NPC189054
0.9051	High Similarity	NPC318575
0.8741	High Similarity	NPC477694
0.8741	High Similarity	NPC477705
0.8686	High Similarity	NPC205915
0.8676	High Similarity	NPC477706
0.8652	High Similarity	NPC282291
0.8652	High Similarity	NPC166137
0.8623	High Similarity	NPC19890
0.8623	High Similarity	NPC110958
0.8552	High Similarity	NPC476336
0.8462	Intermediate Similarity	NPC52664
0.8451	Intermediate Similarity	NPC275150
0.8433	Intermediate Similarity	NPC471927
0.8403	Intermediate Similarity	NPC472564
0.8392	Intermediate Similarity	NPC246474
0.8392	Intermediate Similarity	NPC162851
0.8392	Intermediate Similarity	NPC218092
0.8382	Intermediate Similarity	NPC223807
0.8382	Intermediate Similarity	NPC64948
0.8369	Intermediate Similarity	NPC102260
0.8369	Intermediate Similarity	NPC230968
0.8357	Intermediate Similarity	NPC68779
0.8357	Intermediate Similarity	NPC4982
0.8357	Intermediate Similarity	NPC5310
0.8357	Intermediate Similarity	NPC300776
0.8357	Intermediate Similarity	NPC176814
0.8356	Intermediate Similarity	NPC3982
0.8321	Intermediate Similarity	NPC205502
0.8309	Intermediate Similarity	NPC213711
0.8309	Intermediate Similarity	NPC40352
0.8264	Intermediate Similarity	NPC28398
0.8261	Intermediate Similarity	NPC476748
0.8222	Intermediate Similarity	NPC249788
0.8219	Intermediate Similarity	NPC327623
0.8209	Intermediate Similarity	NPC80241
0.8209	Intermediate Similarity	NPC301641
0.8207	Intermediate Similarity	NPC176586
0.8207	Intermediate Similarity	NPC104956
0.8207	Intermediate Similarity	NPC210354
0.8195	Intermediate Similarity	NPC344161
0.8194	Intermediate Similarity	NPC470855
0.8188	Intermediate Similarity	NPC145569
0.8188	Intermediate Similarity	NPC216223
0.8175	Intermediate Similarity	NPC274356
0.8158	Intermediate Similarity	NPC476364
0.8151	Intermediate Similarity	NPC474288
0.8138	Intermediate Similarity	NPC29599
0.8133	Intermediate Similarity	NPC158635
0.8133	Intermediate Similarity	NPC229882
0.8112	Intermediate Similarity	NPC90431
0.8108	Intermediate Similarity	NPC472560
0.8102	Intermediate Similarity	NPC280767
0.8095	Intermediate Similarity	NPC46880
0.8095	Intermediate Similarity	NPC177644
0.8095	Intermediate Similarity	NPC191158
0.8082	Intermediate Similarity	NPC40237
0.8082	Intermediate Similarity	NPC151423
0.8074	Intermediate Similarity	NPC194416
0.8074	Intermediate Similarity	NPC177291
0.8071	Intermediate Similarity	NPC171550
0.8071	Intermediate Similarity	NPC134764
0.8067	Intermediate Similarity	NPC174512
0.8067	Intermediate Similarity	NPC293757
0.8067	Intermediate Similarity	NPC477698
0.8067	Intermediate Similarity	NPC474965
0.8067	Intermediate Similarity	NPC668
0.8067	Intermediate Similarity	NPC472567
0.8067	Intermediate Similarity	NPC477695
0.8056	Intermediate Similarity	NPC14022
0.8042	Intermediate Similarity	NPC113295
0.8041	Intermediate Similarity	NPC327052
0.803	Intermediate Similarity	NPC471924
0.803	Intermediate Similarity	NPC471925
0.803	Intermediate Similarity	NPC471928
0.8026	Intermediate Similarity	NPC56184
0.8015	Intermediate Similarity	NPC256167
0.8014	Intermediate Similarity	NPC100675
0.8013	Intermediate Similarity	NPC12854
0.8	Intermediate Similarity	NPC262804
0.8	Intermediate Similarity	NPC40654
0.8	Intermediate Similarity	NPC241354
0.7987	Intermediate Similarity	NPC186316
0.7986	Intermediate Similarity	NPC177167
0.7985	Intermediate Similarity	NPC69670
0.7985	Intermediate Similarity	NPC57501
0.7974	Intermediate Similarity	NPC299706
0.7974	Intermediate Similarity	NPC245615
0.7974	Intermediate Similarity	NPC61604
0.7974	Intermediate Similarity	NPC115466
0.7973	Intermediate Similarity	NPC475000
0.7973	Intermediate Similarity	NPC15743
0.7973	Intermediate Similarity	NPC218841
0.7973	Intermediate Similarity	NPC474036
0.7973	Intermediate Similarity	NPC92693
0.7972	Intermediate Similarity	NPC471913
0.7971	Intermediate Similarity	NPC257589
0.7971	Intermediate Similarity	NPC85830
0.7971	Intermediate Similarity	NPC17348
0.7971	Intermediate Similarity	NPC53305
0.797	Intermediate Similarity	NPC471926
0.7961	Intermediate Similarity	NPC164082
0.7961	Intermediate Similarity	NPC477700
0.7961	Intermediate Similarity	NPC163002
0.7959	Intermediate Similarity	NPC253481
0.7959	Intermediate Similarity	NPC253722
0.7959	Intermediate Similarity	NPC31751
0.7958	Intermediate Similarity	NPC239302
0.7958	Intermediate Similarity	NPC104077
0.7958	Intermediate Similarity	NPC259742
0.7958	Intermediate Similarity	NPC147616
0.7958	Intermediate Similarity	NPC227002
0.7958	Intermediate Similarity	NPC219671
0.7956	Intermediate Similarity	NPC163083
0.7956	Intermediate Similarity	NPC244876
0.7956	Intermediate Similarity	NPC470887
0.7949	Intermediate Similarity	NPC472565
0.7949	Intermediate Similarity	NPC179914
0.7943	Intermediate Similarity	NPC275950
0.7941	Intermediate Similarity	NPC201777
0.7941	Intermediate Similarity	NPC114845
0.7935	Intermediate Similarity	NPC478055
0.7933	Intermediate Similarity	NPC101755
0.7933	Intermediate Similarity	NPC104024
0.7933	Intermediate Similarity	NPC80230
0.7933	Intermediate Similarity	NPC304687
0.7933	Intermediate Similarity	NPC65574
0.7931	Intermediate Similarity	NPC166184
0.7922	Intermediate Similarity	NPC30009
0.7922	Intermediate Similarity	NPC103197
0.7919	Intermediate Similarity	NPC474158
0.7919	Intermediate Similarity	NPC223185
0.7917	Intermediate Similarity	NPC252343
0.7917	Intermediate Similarity	NPC211386
0.7917	Intermediate Similarity	NPC174191
0.7914	Intermediate Similarity	NPC92207
0.7914	Intermediate Similarity	NPC127937
0.7908	Intermediate Similarity	NPC477699
0.7905	Intermediate Similarity	NPC137920
0.7905	Intermediate Similarity	NPC125134
0.7905	Intermediate Similarity	NPC106920
0.7905	Intermediate Similarity	NPC273657
0.7905	Intermediate Similarity	NPC86455
0.7902	Intermediate Similarity	NPC327410
0.7902	Intermediate Similarity	NPC169973
0.7898	Intermediate Similarity	NPC476337
0.7891	Intermediate Similarity	NPC51681
0.7887	Intermediate Similarity	NPC476345
0.7871	Intermediate Similarity	NPC38699
0.7867	Intermediate Similarity	NPC193779
0.7857	Intermediate Similarity	NPC158737
0.7857	Intermediate Similarity	NPC245948
0.7847	Intermediate Similarity	NPC37065
0.7847	Intermediate Similarity	NPC47181
0.7847	Intermediate Similarity	NPC45404
0.7846	Intermediate Similarity	NPC31279
0.7843	Intermediate Similarity	NPC32079
0.7843	Intermediate Similarity	NPC178048
0.7842	Intermediate Similarity	NPC173608
0.7838	Intermediate Similarity	NPC287124
0.7836	Intermediate Similarity	NPC212643
0.7836	Intermediate Similarity	NPC199209
0.7834	Intermediate Similarity	NPC475095
0.7832	Intermediate Similarity	NPC106739
0.7832	Intermediate Similarity	NPC471505
0.7829	Intermediate Similarity	NPC262455
0.7829	Intermediate Similarity	NPC127827
0.7829	Intermediate Similarity	NPC177476
0.7823	Intermediate Similarity	NPC147379
0.7821	Intermediate Similarity	NPC237946
0.7821	Intermediate Similarity	NPC163635
0.7821	Intermediate Similarity	NPC32373
0.782	Intermediate Similarity	NPC473264
0.782	Intermediate Similarity	NPC475815
0.782	Intermediate Similarity	NPC47194
0.7817	Intermediate Similarity	NPC181079
0.7817	Intermediate Similarity	NPC172673
0.7817	Intermediate Similarity	NPC173308
0.7815	Intermediate Similarity	NPC25496
0.781	Intermediate Similarity	NPC38996
0.781	Intermediate Similarity	NPC160380
0.7808	Intermediate Similarity	NPC281780
0.7806	Intermediate Similarity	NPC136757
0.7803	Intermediate Similarity	NPC109241
0.7801	Intermediate Similarity	NPC165128
0.7801	Intermediate Similarity	NPC57119
0.7801	Intermediate Similarity	NPC158471
0.7801	Intermediate Similarity	NPC226862
0.7801	Intermediate Similarity	NPC226661
0.7799	Intermediate Similarity	NPC476244
0.7793	Intermediate Similarity	NPC135777
0.7793	Intermediate Similarity	NPC477301
0.7793	Intermediate Similarity	NPC44245
0.7793	Intermediate Similarity	NPC18576
0.7793	Intermediate Similarity	NPC470990
0.7793	Intermediate Similarity	NPC142547
0.7793	Intermediate Similarity	NPC72796
0.7786	Intermediate Similarity	NPC303680

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 NPC52968 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	278
0.1-0.2	855
0.2-0.3	1619
0.3-0.4	2687
0.4-0.5	2119
0.5-0.6	1186
0.6-0.7	371
0.7-0.8	34
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8571	High Similarity	NPD7028	Phase 2
0.8288	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.8077	Intermediate Similarity	NPD7199	Phase 2
0.7975	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7959	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7959	Intermediate Similarity	NPD4110	Phase 3
0.7857	Intermediate Similarity	NPD37	Approved
0.7821	Intermediate Similarity	NPD4967	Phase 2
0.7821	Intermediate Similarity	NPD4966	Approved
0.7821	Intermediate Similarity	NPD4965	Approved
0.7722	Intermediate Similarity	NPD6234	Discontinued
0.7669	Intermediate Similarity	NPD5283	Phase 1
0.7655	Intermediate Similarity	NPD6355	Discontinued
0.7647	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7591	Intermediate Similarity	NPD1357	Approved
0.7554	Intermediate Similarity	NPD3705	Approved
0.7518	Intermediate Similarity	NPD1283	Approved
0.7407	Intermediate Similarity	NPD8127	Discontinued
0.7397	Intermediate Similarity	NPD8032	Phase 2
0.7394	Intermediate Similarity	NPD7228	Approved
0.7379	Intermediate Similarity	NPD7095	Approved
0.7329	Intermediate Similarity	NPD6798	Discontinued
0.7324	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7319	Intermediate Similarity	NPD5536	Phase 2
0.7305	Intermediate Similarity	NPD1281	Approved
0.7259	Intermediate Similarity	NPD228	Approved
0.7254	Intermediate Similarity	NPD1608	Approved
0.725	Intermediate Similarity	NPD5563	Clinical (unspecified phase)
0.7248	Intermediate Similarity	NPD6653	Approved
0.7237	Intermediate Similarity	NPD5958	Discontinued
0.7234	Intermediate Similarity	NPD3847	Discontinued
0.723	Intermediate Similarity	NPD4140	Approved
0.723	Intermediate Similarity	NPD3620	Phase 2
0.723	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD7240	Approved
0.7219	Intermediate Similarity	NPD7685	Pre-registration
0.7215	Intermediate Similarity	NPD7458	Discontinued
0.7172	Intermediate Similarity	NPD5647	Approved
0.7163	Intermediate Similarity	NPD2932	Approved
0.7162	Intermediate Similarity	NPD6233	Phase 2
0.7162	Intermediate Similarity	NPD6663	Approved
0.7153	Intermediate Similarity	NPD1876	Approved
0.7151	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD8166	Discontinued
0.7143	Intermediate Similarity	NPD1894	Discontinued
0.7135	Intermediate Similarity	NPD7280	Phase 3
0.7135	Intermediate Similarity	NPD7281	Phase 3
0.7134	Intermediate Similarity	NPD6273	Approved
0.7114	Intermediate Similarity	NPD2979	Phase 3
0.7114	Intermediate Similarity	NPD4060	Phase 1
0.7105	Intermediate Similarity	NPD2438	Suspended
0.7103	Intermediate Similarity	NPD2797	Approved
0.7097	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.7093	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7092	Intermediate Similarity	NPD1651	Approved
0.7086	Intermediate Similarity	NPD7097	Phase 1
0.7075	Intermediate Similarity	NPD2614	Approved
0.7067	Intermediate Similarity	NPD1933	Approved
0.7059	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD6004	Phase 3
0.7059	Intermediate Similarity	NPD5762	Approved
0.7059	Intermediate Similarity	NPD6002	Phase 3
0.7059	Intermediate Similarity	NPD5763	Approved
0.7059	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD6005	Phase 3
0.7055	Intermediate Similarity	NPD2798	Approved
0.7055	Intermediate Similarity	NPD4624	Approved
0.7047	Intermediate Similarity	NPD4062	Phase 3
0.7042	Intermediate Similarity	NPD4626	Approved
0.7042	Intermediate Similarity	NPD17	Approved
0.7042	Intermediate Similarity	NPD3019	Approved
0.7007	Intermediate Similarity	NPD5736	Approved
0.7007	Intermediate Similarity	NPD9494	Approved
0.6993	Remote Similarity	NPD2935	Discontinued
0.6982	Remote Similarity	NPD3818	Discontinued
0.698	Remote Similarity	NPD3268	Approved
0.6972	Remote Similarity	NPD5585	Approved
0.6962	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD5535	Approved
0.6954	Remote Similarity	NPD3657	Discovery
0.6954	Remote Similarity	NPD447	Suspended
0.6944	Remote Similarity	NPD1535	Discovery
0.6933	Remote Similarity	NPD8455	Phase 2
0.6928	Remote Similarity	NPD2799	Discontinued
0.6923	Remote Similarity	NPD4628	Phase 3
0.6914	Remote Similarity	NPD6873	Phase 2
0.6913	Remote Similarity	NPD3027	Phase 3
0.6908	Remote Similarity	NPD2492	Phase 1
0.6903	Remote Similarity	NPD4534	Discontinued
0.6897	Remote Similarity	NPD1481	Phase 2
0.6892	Remote Similarity	NPD2861	Phase 2
0.689	Remote Similarity	NPD5977	Approved
0.689	Remote Similarity	NPD5978	Approved
0.6883	Remote Similarity	NPD2161	Phase 2
0.6883	Remote Similarity	NPD2531	Phase 2
0.6875	Remote Similarity	NPD3026	Approved
0.6875	Remote Similarity	NPD3023	Approved
0.6871	Remote Similarity	NPD6362	Approved
0.6867	Remote Similarity	NPD3764	Approved
0.6867	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6861	Remote Similarity	NPD3022	Approved
0.6861	Remote Similarity	NPD3021	Approved
0.6859	Remote Similarity	NPD6674	Discontinued
0.6853	Remote Similarity	NPD3025	Approved
0.6853	Remote Similarity	NPD5691	Approved
0.6853	Remote Similarity	NPD3024	Approved
0.6845	Remote Similarity	NPD7315	Approved
0.6845	Remote Similarity	NPD6232	Discontinued
0.6842	Remote Similarity	NPD5735	Approved
0.6839	Remote Similarity	NPD7266	Discontinued
0.6838	Remote Similarity	NPD1358	Approved
0.6832	Remote Similarity	NPD1653	Approved
0.6824	Remote Similarity	NPD7473	Discontinued
0.6815	Remote Similarity	NPD7003	Approved
0.6815	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6815	Remote Similarity	NPD6331	Phase 2
0.6809	Remote Similarity	NPD7157	Approved
0.6806	Remote Similarity	NPD1778	Approved
0.6797	Remote Similarity	NPD6353	Approved
0.6797	Remote Similarity	NPD2653	Approved
0.6788	Remote Similarity	NPD2684	Approved
0.6788	Remote Similarity	NPD3817	Phase 2
0.6786	Remote Similarity	NPD1241	Discontinued
0.6774	Remote Similarity	NPD4477	Approved
0.6774	Remote Similarity	NPD4476	Approved
0.6766	Remote Similarity	NPD6315	Phase 2
0.6765	Remote Similarity	NPD3134	Approved
0.6757	Remote Similarity	NPD3267	Approved
0.6757	Remote Similarity	NPD3266	Approved
0.6757	Remote Similarity	NPD987	Approved
0.6755	Remote Similarity	NPD5109	Approved
0.6755	Remote Similarity	NPD5110	Phase 2
0.6755	Remote Similarity	NPD5111	Phase 2
0.675	Remote Similarity	NPD3146	Approved
0.675	Remote Similarity	NPD3688	Clinical (unspecified phase)
0.6748	Remote Similarity	NPD6876	Approved
0.6748	Remote Similarity	NPD6875	Approved
0.6747	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6742	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6735	Remote Similarity	NPD5327	Phase 3
0.6735	Remote Similarity	NPD4359	Approved
0.6735	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.6731	Remote Similarity	NPD1375	Discontinued
0.673	Remote Similarity	NPD6783	Clinical (unspecified phase)
0.6714	Remote Similarity	NPD7843	Approved
0.6711	Remote Similarity	NPD1726	Clinical (unspecified phase)
0.6711	Remote Similarity	NPD554	Clinical (unspecified phase)
0.671	Remote Similarity	NPD4108	Discontinued
0.671	Remote Similarity	NPD7033	Discontinued
0.6709	Remote Similarity	NPD3750	Approved
0.6705	Remote Similarity	NPD7074	Phase 3
0.6689	Remote Similarity	NPD196	Phase 1
0.6689	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6688	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6688	Remote Similarity	NPD2157	Approved
0.6688	Remote Similarity	NPD4579	Clinical (unspecified phase)
0.6688	Remote Similarity	NPD7596	Clinical (unspecified phase)
0.6686	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD3641	Approved
0.6667	Remote Similarity	NPD1934	Approved
0.6667	Remote Similarity	NPD3639	Approved
0.6667	Remote Similarity	NPD3972	Approved
0.6667	Remote Similarity	NPD6032	Approved
0.6667	Remote Similarity	NPD826	Approved
0.6667	Remote Similarity	NPD7296	Approved
0.6667	Remote Similarity	NPD825	Approved
0.6667	Remote Similarity	NPD3640	Phase 3
0.6667	Remote Similarity	NPD6190	Approved
0.6647	Remote Similarity	NPD5844	Phase 1
0.6647	Remote Similarity	NPD7054	Approved
0.6647	Remote Similarity	NPD3882	Suspended
0.6646	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6646	Remote Similarity	NPD4739	Approved
0.6645	Remote Similarity	NPD2313	Discontinued
0.6644	Remote Similarity	NPD3496	Discontinued
0.663	Remote Similarity	NPD7237	Clinical (unspecified phase)
0.6627	Remote Similarity	NPD2801	Approved
0.6627	Remote Similarity	NPD5494	Approved
0.6627	Remote Similarity	NPD1006	Clinical (unspecified phase)
0.6626	Remote Similarity	NPD4210	Discontinued
0.6626	Remote Similarity	NPD2370	Clinical (unspecified phase)
0.6624	Remote Similarity	NPD2346	Discontinued
0.6624	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6623	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6622	Remote Similarity	NPD2982	Phase 2
0.6622	Remote Similarity	NPD2983	Phase 2
0.6609	Remote Similarity	NPD7472	Approved
0.6606	Remote Similarity	NPD7109	Clinical (unspecified phase)
0.6606	Remote Similarity	NPD6386	Approved
0.6606	Remote Similarity	NPD6385	Approved
0.6606	Remote Similarity	NPD7110	Phase 1
0.6603	Remote Similarity	NPD3748	Approved
0.66	Remote Similarity	NPD258	Approved
0.66	Remote Similarity	NPD257	Approved
0.6596	Remote Similarity	NPD1138	Approved
0.6585	Remote Similarity	NPD3866	Clinical (unspecified phase)
0.6585	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6579	Remote Similarity	NPD2669	Clinical (unspecified phase)
0.6578	Remote Similarity	NPD7680	Approved
0.6577	Remote Similarity	NPD8651	Approved

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