NPASS Compound

Structure

CID15212 OpenBabel06191715342D 28 33 0 0 0 0 0 0 0 0999 V2000 2.9345 0.0827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3956 2.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2617 3.0827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5296 4.0827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2024 4.0827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9345 3.0827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4067 0.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 5.6654 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2709 5.6654 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5296 3.0827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2024 3.0827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0685 2.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3364 1.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2617 4.0827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3956 4.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0685 4.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9345 4.0827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3364 2.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2024 1.0827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0685 1.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9945 0.1045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6637 -0.6386 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.9345 1.0827 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 -3.0048 4.7518 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6036 5.5608 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.2764 5.5608 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.6776 4.7518 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 23 1 0 0 0 0 2 3 2 0 0 0 0 2 10 1 0 0 0 0 3 14 1 0 0 0 0 4 10 2 0 0 0 0 4 15 1 0 0 0 0 5 11 2 0 0 0 0 5 16 1 0 0 0 0 6 12 2 0 0 0 0 6 17 1 0 0 0 0 7 13 1 0 0 0 0 7 24 1 0 0 0 0 8 25 1 0 0 0 0 8 26 1 0 0 0 0 9 27 1 0 0 0 0 9 28 1 0 0 0 0 10 18 1 0 0 0 0 11 12 1 0 0 0 0 11 18 1 0 0 0 0 12 20 1 0 0 0 0 13 18 2 0 0 0 0 13 19 1 0 0 0 0 14 15 2 0 0 0 0 14 25 1 0 0 0 0 15 26 1 0 0 0 0 16 17 2 0 0 0 0 16 27 1 0 0 0 0 17 28 1 0 0 0 0 19 20 2 0 0 0 0 19 21 1 0 0 0 0 20 23 1 0 0 0 0 21 22 2 0 0 0 0 21 24 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	378.07
Volume:	358.237
LogP:	4.35
LogD:	3.323
LogS:	-6.621
# Rotatable Bonds:	2
TPSA:	72.45
# H-Bond Aceptor:	7
# H-Bond Donor:	0
# Rings:	6
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.631
Synthetic Accessibility Score:	2.704
Fsp3:	0.19
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:	-5.227
MDCK Permeability:	5.8750618336489424e-05
Pgp-inhibitor:	0.085
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.001
20% Bioavailability (F20%):	0.004
30% Bioavailability (F30%):	0.004

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.06
Plasma Protein Binding (PPB):	94.01411437988281%
Volume Distribution (VD):	0.686
Pgp-substrate:	1.0322012901306152%

ADMET: Metabolism

CYP1A2-inhibitor:	0.97
CYP1A2-substrate:	0.202
CYP2C19-inhibitor:	0.981
CYP2C19-substrate:	0.092
CYP2C9-inhibitor:	0.857
CYP2C9-substrate:	0.94
CYP2D6-inhibitor:	0.87
CYP2D6-substrate:	0.925
CYP3A4-inhibitor:	0.901
CYP3A4-substrate:	0.114

ADMET: Excretion

Clearance (CL):	14.333
Half-life (T1/2):	0.112

ADMET: Toxicity

hERG Blockers:	0.087
Human Hepatotoxicity (H-HT):	0.101
Drug-inuced Liver Injury (DILI):	0.909
AMES Toxicity:	0.841
Rat Oral Acute Toxicity:	0.049
Maximum Recommended Daily Dose:	0.59
Skin Sensitization:	0.204
Carcinogencity:	0.941
Eye Corrosion:	0.003
Eye Irritation:	0.121
Respiratory Toxicity:	0.428

Download Data

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

Natural Product: NPC15212

Natural Product ID:	NPC15212
*Common Name:**	Neojusticin A
IUPAC Name:	9-(1,3-benzodioxol-5-yl)-5-methoxy-8H-[2]benzofuro[6,5-f][1,3]benzodioxol-6-one
Synonyms:
Standard InCHIKey:	WOELDRZIQLRDQB-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C21H14O7/c1-23-20-12-6-17-16(27-9-28-17)5-11(12)18(13-7-24-21(22)19(13)20)10-2-3-14-15(4-10)26-8-25-14/h2-6H,7-9H2,1H3
SMILES:	COc1c2cc3c(cc2c(c2ccc4c(c2)OCO4)c2COC(=O)c12)OCO3
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL455369
PubChem CID:	5318737
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0001392] Lignans, neolignans and related compounds [CHEMONTID:0001610] Arylnaphthalene lignans

*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
NPO13775	Polygala amarella	Species	Polygalaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10395523]
NPO16045	Justicia procumbens	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11908984]
NPO18042	Geranium nepalense	Species	Geraniaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23006989]
NPO16045	Justicia procumbens	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[3734816]
NPO16045	Justicia procumbens	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8988600]
NPO23835	Swertia angustifolia	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[Article]
NPO23659	Rostellularia procumbens	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[HerDing]
NPO23835	Swertia angustifolia	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18042	Geranium nepalense	Species	Geraniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO23659	Rostellularia procumbens	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[TCMID]
NPO13775	Polygala amarella	Species	Polygalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24094	Pelargonium reniforme	Species	Geraniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23835	Swertia angustifolia	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16045.1	Justicia procumbens var. leucantha	Varieties	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15580	Justicia simplex	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18042	Geranium nepalense	Species	Geraniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23835	Swertia angustifolia	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO16045.1	Justicia procumbens var. leucantha	Varieties	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO15580	Justicia simplex	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO23659	Rostellularia procumbens	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO25670	Aspergillus foveolatus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23369	Hertia intermedia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16045	Justicia procumbens	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15580	Justicia simplex	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20023	Uncaria gambier	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24094	Pelargonium reniforme	Species	Geraniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO796	Diphasiastrum alpinum	Species	Lycopodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23659	Rostellularia procumbens	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO18042	Geranium nepalense	Species	Geraniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24192	Piptoporus australiensis	Species	Fomitopsidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13775	Polygala amarella	Species	Polygalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24448	Haplopappus ciliatus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22467	Kippistia suaedifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23835	Swertia angustifolia	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23325	Doris verrucosa	Species	Dorididae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19177	Euphorbia franckiana	Species	Euphorbiaceae	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
ED50	1
IC50	1

Activity Type	# Activity
Cell Line	1
CELL-LINE	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	ED50	=	9.0	ug ml-1	PMID[451040]
NPT20967	CELL-LINE	Platelet	n.a.	IC50	=	1100.0	nM	PMID[451039]

☑ 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 NPC15212 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	457
0.1-0.2	1849
0.2-0.3	3976
0.3-0.4	10366
0.4-0.5	8274
0.5-0.6	3626
0.6-0.7	7304
0.7-0.8	6590
0.8-0.85	203
0.85-0.9	33
0.9-0.95	14
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
0.9804	High Similarity	NPC78944
0.9803	High Similarity	NPC19600
0.9608	High Similarity	NPC115123
0.9608	High Similarity	NPC239113
0.9477	High Similarity	NPC54179
0.9427	High Similarity	NPC198796
0.9355	High Similarity	NPC473900
0.9304	High Similarity	NPC116838
0.9304	High Similarity	NPC22130
0.9236	High Similarity	NPC474043
0.9211	High Similarity	NPC181464
0.9167	High Similarity	NPC234730
0.915	High Similarity	NPC24193
0.913	High Similarity	NPC471923
0.9097	High Similarity	NPC118332
0.9091	High Similarity	NPC475722
0.9085	High Similarity	NPC184624
0.9074	High Similarity	NPC473531
0.9074	High Similarity	NPC475453
0.9057	High Similarity	NPC65784
0.9026	High Similarity	NPC127827
0.9012	High Similarity	NPC174734
0.9012	High Similarity	NPC474042
0.8994	High Similarity	NPC125713
0.8922	High Similarity	NPC35266
0.8909	High Similarity	NPC129930
0.8909	High Similarity	NPC471922
0.8909	High Similarity	NPC473697
0.8909	High Similarity	NPC471920
0.8909	High Similarity	NPC292712
0.8909	High Similarity	NPC312006
0.8909	High Similarity	NPC474075
0.8909	High Similarity	NPC20114
0.8909	High Similarity	NPC114550
0.8909	High Similarity	NPC471921
0.8902	High Similarity	NPC117911
0.8868	High Similarity	NPC109765
0.8868	High Similarity	NPC301897
0.8812	High Similarity	NPC143328
0.8812	High Similarity	NPC202495
0.8765	High Similarity	NPC191352
0.8765	High Similarity	NPC258322
0.875	High Similarity	NPC196771
0.8713	High Similarity	NPC114120
0.8713	High Similarity	NPC167045
0.8662	High Similarity	NPC177476
0.8662	High Similarity	NPC262455
0.865	High Similarity	NPC239890
0.865	High Similarity	NPC209411
0.8647	High Similarity	NPC161609
0.8647	High Similarity	NPC275690
0.8618	High Similarity	NPC233780
0.8613	High Similarity	NPC286301
0.8613	High Similarity	NPC313063
0.8608	High Similarity	NPC149505
0.8608	High Similarity	NPC300983
0.8589	High Similarity	NPC96593
0.858	High Similarity	NPC193377
0.8571	High Similarity	NPC254163
0.8553	High Similarity	NPC210642
0.8553	High Similarity	NPC13985
0.8537	High Similarity	NPC319749
0.8537	High Similarity	NPC288149
0.8535	High Similarity	NPC104024
0.8535	High Similarity	NPC101755
0.8535	High Similarity	NPC65574
0.8535	High Similarity	NPC80230
0.8535	High Similarity	NPC304687
0.8521	High Similarity	NPC72455
0.8519	High Similarity	NPC261484
0.8509	High Similarity	NPC273578
0.8506	High Similarity	NPC246474
0.8506	High Similarity	NPC162851
0.8506	High Similarity	NPC218092
0.8503	High Similarity	NPC79322
0.85	High Similarity	NPC104353
0.8494	Intermediate Similarity	NPC474301
0.8487	Intermediate Similarity	NPC160425
0.8485	Intermediate Similarity	NPC19948
0.8485	Intermediate Similarity	NPC280778
0.8485	Intermediate Similarity	NPC61141
0.8476	Intermediate Similarity	NPC470637
0.8476	Intermediate Similarity	NPC47623
0.8466	Intermediate Similarity	NPC82733
0.8466	Intermediate Similarity	NPC76458
0.8452	Intermediate Similarity	NPC41853
0.8447	Intermediate Similarity	NPC308555
0.8415	Intermediate Similarity	NPC15764
0.8408	Intermediate Similarity	NPC229787
0.8405	Intermediate Similarity	NPC155063
0.8395	Intermediate Similarity	NPC348849
0.8395	Intermediate Similarity	NPC178195
0.8393	Intermediate Similarity	NPC167479
0.8393	Intermediate Similarity	NPC471180
0.8383	Intermediate Similarity	NPC477884
0.8373	Intermediate Similarity	NPC144843
0.8365	Intermediate Similarity	NPC40654
0.8365	Intermediate Similarity	NPC262804
0.8364	Intermediate Similarity	NPC139876
0.8364	Intermediate Similarity	NPC474770
0.8363	Intermediate Similarity	NPC66804
0.8354	Intermediate Similarity	NPC19947
0.8354	Intermediate Similarity	NPC207584
0.8353	Intermediate Similarity	NPC475964
0.8344	Intermediate Similarity	NPC478238
0.8344	Intermediate Similarity	NPC191158
0.8344	Intermediate Similarity	NPC474036
0.8344	Intermediate Similarity	NPC177644
0.8333	Intermediate Similarity	NPC153008
0.8333	Intermediate Similarity	NPC148497
0.8333	Intermediate Similarity	NPC320471
0.8333	Intermediate Similarity	NPC83049
0.8333	Intermediate Similarity	NPC118162
0.8323	Intermediate Similarity	NPC477689
0.8323	Intermediate Similarity	NPC303519
0.8313	Intermediate Similarity	NPC309335
0.8313	Intermediate Similarity	NPC296540
0.8312	Intermediate Similarity	NPC14022
0.8304	Intermediate Similarity	NPC62640
0.8304	Intermediate Similarity	NPC477881
0.8303	Intermediate Similarity	NPC325122
0.8302	Intermediate Similarity	NPC153620
0.8302	Intermediate Similarity	NPC24257
0.8294	Intermediate Similarity	NPC52598
0.8293	Intermediate Similarity	NPC237946
0.8293	Intermediate Similarity	NPC32373
0.8286	Intermediate Similarity	NPC472663
0.8286	Intermediate Similarity	NPC472662
0.8284	Intermediate Similarity	NPC311912
0.8282	Intermediate Similarity	NPC478213
0.8274	Intermediate Similarity	NPC187923
0.8272	Intermediate Similarity	NPC70320
0.8263	Intermediate Similarity	NPC22324
0.8263	Intermediate Similarity	NPC108767
0.8261	Intermediate Similarity	NPC261322
0.8253	Intermediate Similarity	NPC239818
0.8253	Intermediate Similarity	NPC218471
0.8246	Intermediate Similarity	NPC471181
0.8246	Intermediate Similarity	NPC157522
0.8242	Intermediate Similarity	NPC296044
0.8242	Intermediate Similarity	NPC181168
0.8242	Intermediate Similarity	NPC115281
0.8242	Intermediate Similarity	NPC167098
0.8242	Intermediate Similarity	NPC258644
0.8242	Intermediate Similarity	NPC310206
0.8242	Intermediate Similarity	NPC163527
0.8239	Intermediate Similarity	NPC224687
0.8239	Intermediate Similarity	NPC193779
0.8235	Intermediate Similarity	NPC88557
0.8232	Intermediate Similarity	NPC3273
0.8228	Intermediate Similarity	NPC92693
0.8228	Intermediate Similarity	NPC218841
0.8221	Intermediate Similarity	NPC137125
0.8221	Intermediate Similarity	NPC68882
0.8221	Intermediate Similarity	NPC295646
0.8221	Intermediate Similarity	NPC3744
0.8221	Intermediate Similarity	NPC292460
0.8217	Intermediate Similarity	NPC176586
0.8217	Intermediate Similarity	NPC210354
0.821	Intermediate Similarity	NPC164082
0.821	Intermediate Similarity	NPC119929
0.8204	Intermediate Similarity	NPC109238
0.8204	Intermediate Similarity	NPC34376
0.8198	Intermediate Similarity	NPC199357
0.8193	Intermediate Similarity	NPC50430
0.8193	Intermediate Similarity	NPC68619
0.8193	Intermediate Similarity	NPC113055
0.8187	Intermediate Similarity	NPC477573
0.8187	Intermediate Similarity	NPC85734
0.8187	Intermediate Similarity	NPC477572
0.8187	Intermediate Similarity	NPC477571
0.8187	Intermediate Similarity	NPC477883
0.8187	Intermediate Similarity	NPC32058
0.8182	Intermediate Similarity	NPC261090
0.8176	Intermediate Similarity	NPC471305
0.8176	Intermediate Similarity	NPC470932
0.8176	Intermediate Similarity	NPC234331
0.8176	Intermediate Similarity	NPC27106
0.8171	Intermediate Similarity	NPC244371
0.8171	Intermediate Similarity	NPC57211
0.8171	Intermediate Similarity	NPC103197
0.8171	Intermediate Similarity	NPC30009
0.8165	Intermediate Similarity	NPC125134
0.8165	Intermediate Similarity	NPC137920
0.8165	Intermediate Similarity	NPC86455
0.8161	Intermediate Similarity	NPC477880
0.8161	Intermediate Similarity	NPC477882
0.816	Intermediate Similarity	NPC473732
0.816	Intermediate Similarity	NPC279061
0.816	Intermediate Similarity	NPC220577
0.8155	Intermediate Similarity	NPC18284
0.8155	Intermediate Similarity	NPC273021
0.8155	Intermediate Similarity	NPC125991
0.8155	Intermediate Similarity	NPC478199
0.815	Intermediate Similarity	NPC146803
0.8148	Intermediate Similarity	NPC37220
0.8146	Intermediate Similarity	NPC205721
0.8144	Intermediate Similarity	NPC91634
0.8144	Intermediate Similarity	NPC150943
0.8144	Intermediate Similarity	NPC74749

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 NPC15212 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	391
0.1-0.2	966
0.2-0.3	1663
0.3-0.4	2798
0.4-0.5	1873
0.5-0.6	969
0.6-0.7	359
0.7-0.8	122
0.8-0.85	9
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8485	Intermediate Similarity	NPD6232	Discontinued
0.8333	Intermediate Similarity	NPD7473	Discontinued
0.8293	Intermediate Similarity	NPD4965	Approved
0.8293	Intermediate Similarity	NPD4966	Approved
0.8293	Intermediate Similarity	NPD4967	Phase 2
0.8193	Intermediate Similarity	NPD6234	Discontinued
0.8137	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.811	Intermediate Similarity	NPD37	Approved
0.8079	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.8063	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.8023	Intermediate Similarity	NPD5844	Phase 1
0.7929	Intermediate Similarity	NPD5494	Approved
0.7886	Intermediate Similarity	NPD6559	Discontinued
0.7882	Intermediate Similarity	NPD7199	Phase 2
0.7861	Intermediate Similarity	NPD7228	Approved
0.7821	Intermediate Similarity	NPD1933	Approved
0.7791	Intermediate Similarity	NPD2533	Approved
0.7791	Intermediate Similarity	NPD2534	Approved
0.7791	Intermediate Similarity	NPD2532	Approved
0.7791	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7772	Intermediate Similarity	NPD4420	Approved
0.7765	Intermediate Similarity	NPD919	Approved
0.7759	Intermediate Similarity	NPD3818	Discontinued
0.7711	Intermediate Similarity	NPD3226	Approved
0.7697	Intermediate Similarity	NPD8312	Approved
0.7697	Intermediate Similarity	NPD8313	Approved
0.7692	Intermediate Similarity	NPD3817	Phase 2
0.7688	Intermediate Similarity	NPD2346	Discontinued
0.7684	Intermediate Similarity	NPD7240	Approved
0.7633	Intermediate Similarity	NPD7819	Suspended
0.7606	Intermediate Similarity	NPD5005	Approved
0.7606	Intermediate Similarity	NPD5006	Approved
0.7596	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7574	Intermediate Similarity	NPD1934	Approved
0.7572	Intermediate Similarity	NPD1247	Approved
0.7529	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD2935	Discontinued
0.7514	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7486	Intermediate Similarity	NPD3926	Phase 2
0.7485	Intermediate Similarity	NPD920	Approved
0.7472	Intermediate Similarity	NPD7074	Phase 3
0.7471	Intermediate Similarity	NPD6959	Discontinued
0.7444	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7442	Intermediate Similarity	NPD7768	Phase 2
0.7442	Intermediate Similarity	NPD3882	Suspended
0.7442	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7427	Intermediate Similarity	NPD2801	Approved
0.7421	Intermediate Similarity	NPD2979	Phase 3
0.7416	Intermediate Similarity	NPD7054	Approved
0.7407	Intermediate Similarity	NPD2438	Suspended
0.7407	Intermediate Similarity	NPD5408	Approved
0.7407	Intermediate Similarity	NPD5404	Approved
0.7407	Intermediate Similarity	NPD5405	Approved
0.7407	Intermediate Similarity	NPD5406	Approved
0.7399	Intermediate Similarity	NPD3749	Approved
0.7396	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7396	Intermediate Similarity	NPD7458	Discontinued
0.7386	Intermediate Similarity	NPD1281	Approved
0.7386	Intermediate Similarity	NPD3705	Approved
0.7375	Intermediate Similarity	NPD447	Suspended
0.7374	Intermediate Similarity	NPD7472	Approved
0.7365	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7363	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7353	Intermediate Similarity	NPD6599	Discontinued
0.7346	Intermediate Similarity	NPD3748	Approved
0.7345	Intermediate Similarity	NPD6166	Phase 2
0.7345	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7345	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD7003	Approved
0.7326	Intermediate Similarity	NPD1465	Phase 2
0.7326	Intermediate Similarity	NPD8455	Phase 2
0.7326	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD7411	Suspended
0.7296	Intermediate Similarity	NPD3764	Approved
0.7292	Intermediate Similarity	NPD7680	Approved
0.7282	Intermediate Similarity	NPD8151	Discontinued
0.7273	Intermediate Similarity	NPD1243	Approved
0.7273	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7253	Intermediate Similarity	NPD7808	Phase 3
0.7246	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7244	Intermediate Similarity	NPD1283	Approved
0.7239	Intermediate Similarity	NPD2799	Discontinued
0.7238	Intermediate Similarity	NPD6797	Phase 2
0.7232	Intermediate Similarity	NPD5710	Approved
0.7232	Intermediate Similarity	NPD7229	Phase 3
0.7232	Intermediate Similarity	NPD5711	Approved
0.7208	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7208	Intermediate Similarity	NPD7783	Phase 2
0.7202	Intermediate Similarity	NPD7435	Discontinued
0.7202	Intermediate Similarity	NPD1511	Approved
0.7202	Intermediate Similarity	NPD6799	Approved
0.72	Intermediate Similarity	NPD7075	Discontinued
0.72	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7198	Intermediate Similarity	NPD7251	Discontinued
0.7195	Intermediate Similarity	NPD2796	Approved
0.719	Intermediate Similarity	NPD5691	Approved
0.7188	Intermediate Similarity	NPD2313	Discontinued
0.717	Intermediate Similarity	NPD6832	Phase 2
0.7169	Intermediate Similarity	NPD6674	Discontinued
0.7168	Intermediate Similarity	NPD6801	Discontinued
0.7167	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD4380	Phase 2
0.7151	Intermediate Similarity	NPD7028	Phase 2
0.7135	Intermediate Similarity	NPD6781	Approved
0.7135	Intermediate Similarity	NPD6777	Approved
0.7135	Intermediate Similarity	NPD6779	Approved
0.7135	Intermediate Similarity	NPD6778	Approved
0.7135	Intermediate Similarity	NPD6780	Approved
0.7135	Intermediate Similarity	NPD6782	Approved
0.7135	Intermediate Similarity	NPD6776	Approved
0.7127	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD3750	Approved
0.7126	Intermediate Similarity	NPD4628	Phase 3
0.7126	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7125	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7118	Intermediate Similarity	NPD1512	Approved
0.711	Intermediate Similarity	NPD6386	Approved
0.711	Intermediate Similarity	NPD6385	Approved
0.7104	Intermediate Similarity	NPD7685	Pre-registration
0.7095	Intermediate Similarity	NPD5242	Approved
0.7091	Intermediate Similarity	NPD1551	Phase 2
0.7091	Intermediate Similarity	NPD2531	Phase 2
0.7086	Intermediate Similarity	NPD5402	Approved
0.7086	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7079	Intermediate Similarity	NPD8127	Discontinued
0.7078	Intermediate Similarity	NPD1651	Approved
0.7077	Intermediate Similarity	NPD7870	Phase 2
0.7077	Intermediate Similarity	NPD7871	Phase 2
0.7072	Intermediate Similarity	NPD3751	Discontinued
0.7062	Intermediate Similarity	NPD6823	Phase 2
0.7044	Intermediate Similarity	NPD2798	Approved
0.7039	Intermediate Similarity	NPD3787	Discontinued
0.703	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD1510	Phase 2
0.7026	Intermediate Similarity	NPD7698	Approved
0.7026	Intermediate Similarity	NPD7697	Approved
0.7026	Intermediate Similarity	NPD7696	Phase 3
0.7018	Intermediate Similarity	NPD6273	Approved
0.7012	Intermediate Similarity	NPD1607	Approved
0.7005	Intermediate Similarity	NPD8150	Discontinued
0.7	Intermediate Similarity	NPD7390	Discontinued
0.6994	Remote Similarity	NPD4307	Phase 2
0.6985	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6985	Remote Similarity	NPD7874	Approved
0.6978	Remote Similarity	NPD7177	Discontinued
0.6975	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD5401	Approved
0.6959	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6946	Remote Similarity	NPD2344	Approved
0.6946	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6946	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6946	Remote Similarity	NPD1471	Phase 3
0.6943	Remote Similarity	NPD1611	Approved
0.6931	Remote Similarity	NPD7930	Approved
0.6923	Remote Similarity	NPD4626	Approved
0.6905	Remote Similarity	NPD1549	Phase 2
0.689	Remote Similarity	NPD1240	Approved
0.6884	Remote Similarity	NPD7701	Phase 2
0.6882	Remote Similarity	NPD5084	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD5403	Approved
0.6875	Remote Similarity	NPD6534	Approved
0.6875	Remote Similarity	NPD6535	Approved
0.6875	Remote Similarity	NPD1470	Approved
0.6871	Remote Similarity	NPD6798	Discontinued
0.6869	Remote Similarity	NPD7999	Approved
0.6864	Remote Similarity	NPD2800	Approved
0.6848	Remote Similarity	NPD230	Phase 1
0.6835	Remote Similarity	NPD1201	Approved
0.6835	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6832	Remote Similarity	NPD1019	Discontinued
0.6829	Remote Similarity	NPD8032	Phase 2
0.6828	Remote Similarity	NPD7038	Approved
0.6828	Remote Similarity	NPD7039	Approved
0.6826	Remote Similarity	NPD4308	Phase 3
0.6825	Remote Similarity	NPD8434	Phase 2
0.6824	Remote Similarity	NPD4110	Phase 3
0.6824	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6821	Remote Similarity	NPD1940	Clinical (unspecified phase)
0.6821	Remote Similarity	NPD8285	Discontinued
0.6818	Remote Similarity	NPD8320	Phase 1
0.6818	Remote Similarity	NPD8319	Approved
0.6818	Remote Similarity	NPD6873	Phase 2
0.6815	Remote Similarity	NPD17	Approved
0.6813	Remote Similarity	NPD1876	Approved
0.6798	Remote Similarity	NPD5353	Approved
0.6798	Remote Similarity	NPD5616	Clinical (unspecified phase)
0.6788	Remote Similarity	NPD4060	Phase 1
0.6784	Remote Similarity	NPD2309	Approved
0.6782	Remote Similarity	NPD7801	Approved
0.6778	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.6771	Remote Similarity	NPD7296	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