NPASS Compound

Structure

CID73911 OpenBabel06191715412D 28 30 0 0 1 0 0 0 0 0999 V2000 4.5468 -0.2024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6554 -2.9474 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8147 -2.2024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0468 -5.0685 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4128 -1.7024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9487 -1.7024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8147 -1.2024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4128 -2.7024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8147 -4.2024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8147 -3.2024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5000 -0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5468 -4.2024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5468 -1.2024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7044 -3.2564 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0827 -1.2024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6808 -1.7024 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.1691 -1.6092 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.5468 -3.2024 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.6808 -4.7024 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.9781 -0.2079 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6808 -2.7024 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.5468 -4.2024 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 6.0468 -3.3364 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.4965 -4.2346 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.6808 -5.7024 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7213 0.4612 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 -0.0388 -2.5873 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 13 2 0 0 0 0 2 14 1 0 0 0 0 5 8 1 0 0 0 0 5 13 1 0 0 0 0 6 7 1 0 0 0 0 6 15 2 0 0 0 0 7 16 1 0 0 0 0 8 18 1 0 0 0 0 9 10 1 0 0 0 0 9 19 1 0 0 0 0 10 21 1 0 0 0 0 11 17 1 0 0 0 0 11 27 1 0 0 0 0 12 22 1 0 0 0 0 12 23 1 0 0 0 0 13 16 1 0 0 0 0 14 24 2 0 0 0 0 14 28 1 0 0 0 0 15 17 1 0 0 0 0 15 20 1 0 0 0 0 16 21 1 6 0 0 0 17 28 1 6 0 0 0 18 21 1 6 0 0 0 18 22 1 0 0 0 0 19 22 1 6 0 0 0 19 25 1 0 0 0 0 20 26 2 0 0 0 0 20 27 1 0 0 0 0 21 3 1 6 0 0 0 22 4 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	392.22
Volume:	405.594
LogP:	2.158
LogD:	1.533
LogS:	-3.667
# Rotatable Bonds:	5
TPSA:	93.06
# H-Bond Aceptor:	6
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.564
Synthetic Accessibility Score:	4.86
Fsp3:	0.727
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.831
MDCK Permeability:	8.4230414358899e-05
Pgp-inhibitor:	0.056
Pgp-substrate:	0.181
Human Intestinal Absorption (HIA):	0.015
20% Bioavailability (F20%):	0.058
30% Bioavailability (F30%):	0.161

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.851
Plasma Protein Binding (PPB):	35.316776275634766%
Volume Distribution (VD):	0.761
Pgp-substrate:	57.32550048828125%

ADMET: Metabolism

CYP1A2-inhibitor:	0.021
CYP1A2-substrate:	0.056
CYP2C19-inhibitor:	0.012
CYP2C19-substrate:	0.141
CYP2C9-inhibitor:	0.003
CYP2C9-substrate:	0.053
CYP2D6-inhibitor:	0.006
CYP2D6-substrate:	0.167
CYP3A4-inhibitor:	0.474
CYP3A4-substrate:	0.257

ADMET: Excretion

Clearance (CL):	4.065
Half-life (T1/2):	0.685

ADMET: Toxicity

hERG Blockers:	0.03
Human Hepatotoxicity (H-HT):	0.085
Drug-inuced Liver Injury (DILI):	0.177
AMES Toxicity:	0.807
Rat Oral Acute Toxicity:	0.523
Maximum Recommended Daily Dose:	0.944
Skin Sensitization:	0.233
Carcinogencity:	0.031
Eye Corrosion:	0.019
Eye Irritation:	0.297
Respiratory Toxicity:	0.618

Download Data

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

Natural Product: NPC73911

Natural Product ID:	NPC73911
*Common Name:**	14-Acetylandrographolide
IUPAC Name:	[(3S,4E)-4-[2-[(1R,4aS,5R,6R,8aS)-6-hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-2-methylidene-3,4,4a,6,7,8-hexahydro-1H-naphthalen-1-yl]ethylidene]-5-oxooxolan-3-yl] acetate
Synonyms:
Standard InCHIKey:	BIBPDMPNXWHNPK-QJAZYMEMSA-N
Standard InCHI:	InChI=1S/C22H32O6/c1-13-5-8-18-21(3,10-9-19(25)22(18,4)12-23)16(13)7-6-15-17(28-14(2)24)11-27-20(15)26/h6,16-19,23,25H,1,5,7-12H2,2-4H3/b15-6+/t16-,17-,18+,19-,21+,22+/m1/s1
SMILES:	C=C1CC[C@H]2[C@@](C)(CC[C@H]([C@@]2(C)CO)O)[C@@H]1C/C=C/1[C@@H](COC1=O)OC(=O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2436069
PubChem CID:	73353957
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000050] Lactones [CHEMONTID:0001245] Gamma butyrolactones

*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
NPO3578	Andrographis paniculata	Species	Acanthaceae	Eukaryota	n.a.	leaf	n.a.	PMID[15894448]
NPO3578	Andrographis paniculata	Species	Acanthaceae	Eukaryota	n.a.	root	n.a.	PMID[15894448]
NPO3578	Andrographis paniculata	Species	Acanthaceae	Eukaryota	aerial parts	purchased in Juhuacun herbal market, Kunming, Yunnan Province, China	2002-Oct	PMID[16562826]
NPO3578	Andrographis paniculata	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18357994]
NPO3578	Andrographis paniculata	Species	Acanthaceae	Eukaryota	n.a.	leaf	n.a.	PMID[21598983]
NPO3578	Andrographis paniculata	Species	Acanthaceae	Eukaryota	n.a.	leaf	n.a.	PMID[22026410]
NPO3578	Andrographis paniculata	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8377022]
NPO3578	Andrographis paniculata	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO3578	Andrographis paniculata	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3578	Andrographis paniculata	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO3578	Andrographis paniculata	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO3578	Andrographis paniculata	Species	Acanthaceae	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
GI50	1
MIC	7
Others	8

Activity Type	# Activity
Cell Line	1
CELL-LINE	1
NON-MOLECULAR	3
Organism	11

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT83	Cell Line	MCF7	Homo sapiens	GI50	=	5490.0	nM	PMID[569042]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	Activity	=	13.0	%	PMID[569041]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	Activity	=	15.0	%	PMID[569041]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	Activity	=	7.0	%	PMID[569041]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	19.0	%	PMID[569041]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	17.0	%	PMID[569041]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	16.0	ug.mL-1	PMID[569043]
NPT729	Organism	Micrococcus luteus	Micrococcus luteus	MIC	=	32.0	ug.mL-1	PMID[569043]
NPT1209	Organism	Pseudomonas fluorescens	Pseudomonas fluorescens	MIC	=	4.0	ug.mL-1	PMID[569043]
NPT20950	CELL-LINE	Erythrocyte	n.a.	Activity	=	4.8	%	PMID[569043]
NPT20	Organism	Candida albicans	Candida albicans	MIC	=	32.0	ug.mL-1	PMID[569043]
NPT923	Organism	Rhizopus oryzae	Rhizopus oryzae	MIC	>	128.0	ug.mL-1	PMID[569043]
NPT87	Organism	Aspergillus fumigatus	Aspergillus fumigatus	MIC	>	128.0	ug.mL-1	PMID[569043]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	=	64.0	ug.mL-1	PMID[569043]

☑ 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 NPC73911 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	179
0.1-0.2	1016
0.2-0.3	3710
0.3-0.4	7112
0.4-0.5	14161
0.5-0.6	6380
0.6-0.7	6975
0.7-0.8	2923
0.8-0.85	207
0.85-0.9	23
0.9-0.95	6
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
0.9674	High Similarity	NPC124512
0.9674	High Similarity	NPC278386
0.9674	High Similarity	NPC159763
0.9444	High Similarity	NPC72845
0.9032	High Similarity	NPC57117
0.9011	High Similarity	NPC50488
0.9011	High Similarity	NPC474396
0.8854	High Similarity	NPC473154
0.8842	High Similarity	NPC242848
0.8804	High Similarity	NPC79027
0.8723	High Similarity	NPC162615
0.8723	High Similarity	NPC53555
0.8723	High Similarity	NPC152778
0.8723	High Similarity	NPC205034
0.8723	High Similarity	NPC139692
0.871	High Similarity	NPC78973
0.8681	High Similarity	NPC329692
0.8681	High Similarity	NPC131813
0.8673	High Similarity	NPC303559
0.8654	High Similarity	NPC264153
0.8646	High Similarity	NPC16967
0.8571	High Similarity	NPC476602
0.8571	High Similarity	NPC476299
0.8571	High Similarity	NPC474012
0.8557	High Similarity	NPC474343
0.8542	High Similarity	NPC183012
0.8511	High Similarity	NPC310479
0.8454	Intermediate Similarity	NPC473153
0.8454	Intermediate Similarity	NPC134072
0.8454	Intermediate Similarity	NPC234993
0.8447	Intermediate Similarity	NPC475065
0.8438	Intermediate Similarity	NPC191521
0.8431	Intermediate Similarity	NPC187435
0.8431	Intermediate Similarity	NPC329048
0.8431	Intermediate Similarity	NPC67321
0.8431	Intermediate Similarity	NPC330011
0.8421	Intermediate Similarity	NPC472814
0.8421	Intermediate Similarity	NPC177037
0.84	Intermediate Similarity	NPC476081
0.8387	Intermediate Similarity	NPC166857
0.8387	Intermediate Similarity	NPC473891
0.8384	Intermediate Similarity	NPC47024
0.8384	Intermediate Similarity	NPC38855
0.8381	Intermediate Similarity	NPC269530
0.8351	Intermediate Similarity	NPC276110
0.8351	Intermediate Similarity	NPC476519
0.835	Intermediate Similarity	NPC318363
0.835	Intermediate Similarity	NPC473482
0.835	Intermediate Similarity	NPC306265
0.835	Intermediate Similarity	NPC475418
0.8333	Intermediate Similarity	NPC472812
0.8317	Intermediate Similarity	NPC120321
0.8317	Intermediate Similarity	NPC476237
0.8316	Intermediate Similarity	NPC51486
0.8316	Intermediate Similarity	NPC221111
0.8316	Intermediate Similarity	NPC280149
0.8316	Intermediate Similarity	NPC182136
0.83	Intermediate Similarity	NPC473160
0.8298	Intermediate Similarity	NPC104560
0.8283	Intermediate Similarity	NPC316598
0.8283	Intermediate Similarity	NPC474440
0.8261	Intermediate Similarity	NPC96055
0.8247	Intermediate Similarity	NPC470697
0.8241	Intermediate Similarity	NPC167606
0.8241	Intermediate Similarity	NPC140055
0.8241	Intermediate Similarity	NPC183580
0.8241	Intermediate Similarity	NPC286528
0.8241	Intermediate Similarity	NPC20302
0.8241	Intermediate Similarity	NPC470492
0.8241	Intermediate Similarity	NPC470493
0.8241	Intermediate Similarity	NPC312824
0.8241	Intermediate Similarity	NPC473656
0.8235	Intermediate Similarity	NPC296950
0.8235	Intermediate Similarity	NPC146731
0.8229	Intermediate Similarity	NPC233345
0.8229	Intermediate Similarity	NPC472811
0.8229	Intermediate Similarity	NPC186363
0.8224	Intermediate Similarity	NPC147912
0.8224	Intermediate Similarity	NPC67259
0.8218	Intermediate Similarity	NPC32577
0.8218	Intermediate Similarity	NPC283343
0.8218	Intermediate Similarity	NPC258547
0.8218	Intermediate Similarity	NPC273668
0.8218	Intermediate Similarity	NPC155332
0.8218	Intermediate Similarity	NPC114540
0.8211	Intermediate Similarity	NPC77001
0.8211	Intermediate Similarity	NPC174342
0.8211	Intermediate Similarity	NPC253618
0.8211	Intermediate Similarity	NPC82876
0.82	Intermediate Similarity	NPC117685
0.82	Intermediate Similarity	NPC476303
0.8182	Intermediate Similarity	NPC475709
0.8182	Intermediate Similarity	NPC253826
0.8182	Intermediate Similarity	NPC287668
0.8173	Intermediate Similarity	NPC189075
0.8173	Intermediate Similarity	NPC275539
0.8172	Intermediate Similarity	NPC35933
0.8172	Intermediate Similarity	NPC30984
0.8165	Intermediate Similarity	NPC50774
0.8165	Intermediate Similarity	NPC709
0.8163	Intermediate Similarity	NPC209355
0.8155	Intermediate Similarity	NPC88349
0.8155	Intermediate Similarity	NPC477125
0.8152	Intermediate Similarity	NPC311070
0.8152	Intermediate Similarity	NPC79945
0.8144	Intermediate Similarity	NPC115021
0.8137	Intermediate Similarity	NPC176883
0.8137	Intermediate Similarity	NPC112009
0.8137	Intermediate Similarity	NPC159533
0.8137	Intermediate Similarity	NPC297617
0.8137	Intermediate Similarity	NPC476889
0.8137	Intermediate Similarity	NPC471938
0.8132	Intermediate Similarity	NPC159148
0.8132	Intermediate Similarity	NPC170303
0.8131	Intermediate Similarity	NPC122056
0.8131	Intermediate Similarity	NPC477126
0.8119	Intermediate Similarity	NPC471412
0.8113	Intermediate Similarity	NPC474315
0.81	Intermediate Similarity	NPC478056
0.81	Intermediate Similarity	NPC216478
0.81	Intermediate Similarity	NPC57079
0.81	Intermediate Similarity	NPC218107
0.81	Intermediate Similarity	NPC108368
0.8095	Intermediate Similarity	NPC42662
0.8095	Intermediate Similarity	NPC474243
0.8091	Intermediate Similarity	NPC264954
0.8081	Intermediate Similarity	NPC195366
0.8081	Intermediate Similarity	NPC114743
0.8081	Intermediate Similarity	NPC88009
0.8077	Intermediate Similarity	NPC473284
0.8077	Intermediate Similarity	NPC255387
0.8077	Intermediate Similarity	NPC131665
0.8077	Intermediate Similarity	NPC110496
0.8061	Intermediate Similarity	NPC105490
0.8058	Intermediate Similarity	NPC471937
0.8041	Intermediate Similarity	NPC329842
0.8039	Intermediate Similarity	NPC476890
0.8039	Intermediate Similarity	NPC472552
0.8039	Intermediate Similarity	NPC475038
0.8039	Intermediate Similarity	NPC471914
0.8039	Intermediate Similarity	NPC472815
0.8039	Intermediate Similarity	NPC109195
0.8039	Intermediate Similarity	NPC40918
0.8037	Intermediate Similarity	NPC470063
0.8037	Intermediate Similarity	NPC69291
0.8037	Intermediate Similarity	NPC476801
0.8022	Intermediate Similarity	NPC281880
0.8021	Intermediate Similarity	NPC246028
0.8021	Intermediate Similarity	NPC314727
0.8021	Intermediate Similarity	NPC168131
0.802	Intermediate Similarity	NPC201406
0.802	Intermediate Similarity	NPC251680
0.802	Intermediate Similarity	NPC474190
0.802	Intermediate Similarity	NPC471413
0.802	Intermediate Similarity	NPC473510
0.8019	Intermediate Similarity	NPC478209
0.8019	Intermediate Similarity	NPC235014
0.8018	Intermediate Similarity	NPC474370
0.8	Intermediate Similarity	NPC181103
0.8	Intermediate Similarity	NPC475372
0.8	Intermediate Similarity	NPC186525
0.8	Intermediate Similarity	NPC94377
0.8	Intermediate Similarity	NPC151681
0.8	Intermediate Similarity	NPC38948
0.8	Intermediate Similarity	NPC305029
0.8	Intermediate Similarity	NPC132753
0.8	Intermediate Similarity	NPC475263
0.8	Intermediate Similarity	NPC210337
0.8	Intermediate Similarity	NPC51499
0.8	Intermediate Similarity	NPC175351
0.8	Intermediate Similarity	NPC121402
0.8	Intermediate Similarity	NPC2049
0.8	Intermediate Similarity	NPC476802
0.8	Intermediate Similarity	NPC224356
0.8	Intermediate Similarity	NPC89171
0.7982	Intermediate Similarity	NPC64318
0.7982	Intermediate Similarity	NPC268954
0.7982	Intermediate Similarity	NPC470075
0.7982	Intermediate Similarity	NPC44170
0.7981	Intermediate Similarity	NPC173172
0.7981	Intermediate Similarity	NPC218158
0.7981	Intermediate Similarity	NPC475414
0.7981	Intermediate Similarity	NPC266570
0.7981	Intermediate Similarity	NPC34768
0.798	Intermediate Similarity	NPC259042
0.798	Intermediate Similarity	NPC157686
0.798	Intermediate Similarity	NPC471786
0.798	Intermediate Similarity	NPC37603
0.7979	Intermediate Similarity	NPC65661
0.7979	Intermediate Similarity	NPC474013
0.7979	Intermediate Similarity	NPC86316
0.7979	Intermediate Similarity	NPC106416
0.7979	Intermediate Similarity	NPC329738
0.7963	Intermediate Similarity	NPC478212
0.7961	Intermediate Similarity	NPC95899
0.7961	Intermediate Similarity	NPC474165
0.7961	Intermediate Similarity	NPC72151
0.7961	Intermediate Similarity	NPC475526
0.7961	Intermediate Similarity	NPC69171
0.7961	Intermediate Similarity	NPC180204

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 NPC73911 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	1245
0.2-0.3	3560
0.3-0.4	2686
0.4-0.5	974
0.5-0.6	236
0.6-0.7	233
0.7-0.8	63
0.8-0.85	4
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9674	High Similarity	NPD4225	Approved
0.8241	Intermediate Similarity	NPD7115	Discovery
0.81	Intermediate Similarity	NPD7638	Approved
0.802	Intermediate Similarity	NPD7639	Approved
0.802	Intermediate Similarity	NPD7640	Approved
0.7664	Intermediate Similarity	NPD6686	Approved
0.766	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7637	Suspended
0.7451	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7429	Intermediate Similarity	NPD5344	Discontinued
0.7423	Intermediate Similarity	NPD1694	Approved
0.74	Intermediate Similarity	NPD5785	Approved
0.7358	Intermediate Similarity	NPD7632	Discontinued
0.7353	Intermediate Similarity	NPD7748	Approved
0.7327	Intermediate Similarity	NPD7515	Phase 2
0.7308	Intermediate Similarity	NPD7902	Approved
0.7273	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7255	Intermediate Similarity	NPD6399	Phase 3
0.7232	Intermediate Similarity	NPD8297	Approved
0.7207	Intermediate Similarity	NPD6371	Approved
0.7207	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7182	Intermediate Similarity	NPD6881	Approved
0.7182	Intermediate Similarity	NPD6899	Approved
0.7172	Intermediate Similarity	NPD3618	Phase 1
0.717	Intermediate Similarity	NPD6648	Approved
0.7157	Intermediate Similarity	NPD6411	Approved
0.7156	Intermediate Similarity	NPD7128	Approved
0.7156	Intermediate Similarity	NPD5739	Approved
0.7156	Intermediate Similarity	NPD6675	Approved
0.7156	Intermediate Similarity	NPD6402	Approved
0.7143	Intermediate Similarity	NPD6400	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6649	Approved
0.7143	Intermediate Similarity	NPD6650	Approved
0.7117	Intermediate Similarity	NPD6373	Approved
0.7117	Intermediate Similarity	NPD6372	Approved
0.7091	Intermediate Similarity	NPD5697	Approved
0.7091	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7087	Intermediate Similarity	NPD5779	Approved
0.7087	Intermediate Similarity	NPD5778	Approved
0.7069	Intermediate Similarity	NPD7328	Approved
0.7069	Intermediate Similarity	NPD7327	Approved
0.7059	Intermediate Similarity	NPD46	Approved
0.7059	Intermediate Similarity	NPD6698	Approved
0.7059	Intermediate Similarity	NPD7838	Discovery
0.7054	Intermediate Similarity	NPD7290	Approved
0.7054	Intermediate Similarity	NPD7102	Approved
0.7054	Intermediate Similarity	NPD6883	Approved
0.7049	Intermediate Similarity	NPD7319	Approved
0.7034	Intermediate Similarity	NPD8033	Approved
0.7027	Intermediate Similarity	NPD7320	Approved
0.7027	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD7900	Approved
0.7019	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7009	Intermediate Similarity	NPD7516	Approved
0.7	Intermediate Similarity	NPD7492	Approved
0.6991	Remote Similarity	NPD6847	Approved
0.6991	Remote Similarity	NPD6617	Approved
0.6991	Remote Similarity	NPD6869	Approved
0.6991	Remote Similarity	NPD8130	Phase 1
0.699	Remote Similarity	NPD6079	Approved
0.6981	Remote Similarity	NPD6084	Phase 2
0.6981	Remote Similarity	NPD6083	Phase 2
0.6964	Remote Similarity	NPD6014	Approved
0.6964	Remote Similarity	NPD6012	Approved
0.6964	Remote Similarity	NPD6013	Approved
0.6961	Remote Similarity	NPD5328	Approved
0.6961	Remote Similarity	NPD6101	Approved
0.6961	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6949	Remote Similarity	NPD6319	Approved
0.6949	Remote Similarity	NPD6054	Approved
0.6949	Remote Similarity	NPD8294	Approved
0.6949	Remote Similarity	NPD8377	Approved
0.6942	Remote Similarity	NPD7507	Approved
0.6942	Remote Similarity	NPD6616	Approved
0.6937	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6937	Remote Similarity	NPD5701	Approved
0.693	Remote Similarity	NPD6882	Approved
0.6916	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.69	Remote Similarity	NPD5363	Approved
0.6891	Remote Similarity	NPD8379	Approved
0.6891	Remote Similarity	NPD8335	Approved
0.6891	Remote Similarity	NPD7503	Approved
0.6891	Remote Similarity	NPD8296	Approved
0.6891	Remote Similarity	NPD8380	Approved
0.6891	Remote Similarity	NPD8378	Approved
0.6885	Remote Similarity	NPD7078	Approved
0.6875	Remote Similarity	NPD6011	Approved
0.6833	Remote Similarity	NPD6370	Approved
0.6832	Remote Similarity	NPD6684	Approved
0.6832	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6832	Remote Similarity	NPD7334	Approved
0.6832	Remote Similarity	NPD6409	Approved
0.6832	Remote Similarity	NPD7521	Approved
0.6832	Remote Similarity	NPD7146	Approved
0.6832	Remote Similarity	NPD5330	Approved
0.6829	Remote Similarity	NPD7736	Approved
0.6827	Remote Similarity	NPD8034	Phase 2
0.6827	Remote Similarity	NPD8035	Phase 2
0.6807	Remote Similarity	NPD6059	Approved
0.6804	Remote Similarity	NPD7645	Phase 2
0.68	Remote Similarity	NPD4786	Approved
0.6796	Remote Similarity	NPD6051	Approved
0.6792	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6777	Remote Similarity	NPD8328	Phase 3
0.6768	Remote Similarity	NPD3667	Approved
0.6768	Remote Similarity	NPD5209	Approved
0.6765	Remote Similarity	NPD7524	Approved
0.6759	Remote Similarity	NPD5696	Approved
0.675	Remote Similarity	NPD6015	Approved
0.675	Remote Similarity	NPD6016	Approved
0.6748	Remote Similarity	NPD8293	Discontinued
0.6735	Remote Similarity	NPD7525	Registered
0.6733	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6733	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6729	Remote Similarity	NPD5221	Approved
0.6729	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6729	Remote Similarity	NPD5222	Approved
0.6729	Remote Similarity	NPD4697	Phase 3
0.6727	Remote Similarity	NPD5211	Phase 2
0.6724	Remote Similarity	NPD4632	Approved
0.67	Remote Similarity	NPD6695	Phase 3
0.6699	Remote Similarity	NPD6903	Approved
0.6699	Remote Similarity	NPD5737	Approved
0.6699	Remote Similarity	NPD6672	Approved
0.6699	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6697	Remote Similarity	NPD5286	Approved
0.6697	Remote Similarity	NPD5285	Approved
0.6697	Remote Similarity	NPD4696	Approved
0.6696	Remote Similarity	NPD6008	Approved
0.6696	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6694	Remote Similarity	NPD5988	Approved
0.6667	Remote Similarity	NPD5173	Approved
0.6667	Remote Similarity	NPD4755	Approved
0.6637	Remote Similarity	NPD6412	Phase 2
0.6636	Remote Similarity	NPD5695	Phase 3
0.6634	Remote Similarity	NPD3665	Phase 1
0.6634	Remote Similarity	NPD3666	Approved
0.6634	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6634	Remote Similarity	NPD3133	Approved
0.6612	Remote Similarity	NPD8517	Approved
0.6612	Remote Similarity	NPD8515	Approved
0.6612	Remote Similarity	NPD8516	Approved
0.6612	Remote Similarity	NPD8513	Phase 3
0.661	Remote Similarity	NPD6274	Approved
0.661	Remote Similarity	NPD6868	Approved
0.6609	Remote Similarity	NPD4634	Approved
0.6607	Remote Similarity	NPD5141	Approved
0.6604	Remote Similarity	NPD4202	Approved
0.6602	Remote Similarity	NPD3573	Approved
0.66	Remote Similarity	NPD4269	Approved
0.66	Remote Similarity	NPD4270	Approved
0.6583	Remote Similarity	NPD7100	Approved
0.6583	Remote Similarity	NPD7101	Approved
0.6577	Remote Similarity	NPD5226	Approved
0.6577	Remote Similarity	NPD5225	Approved
0.6577	Remote Similarity	NPD4633	Approved
0.6577	Remote Similarity	NPD5224	Approved
0.6566	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6566	Remote Similarity	NPD4695	Discontinued
0.6562	Remote Similarity	NPD7339	Approved
0.6562	Remote Similarity	NPD6942	Approved
0.6555	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6555	Remote Similarity	NPD6009	Approved
0.6545	Remote Similarity	NPD4700	Approved
0.6542	Remote Similarity	NPD5282	Discontinued
0.6535	Remote Similarity	NPD7154	Phase 3
0.6522	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6518	Remote Similarity	NPD5174	Approved
0.6518	Remote Similarity	NPD5175	Approved
0.6509	Remote Similarity	NPD5693	Phase 1
0.6509	Remote Similarity	NPD7983	Approved
0.6505	Remote Similarity	NPD5786	Approved
0.6504	Remote Similarity	NPD7604	Phase 2
0.65	Remote Similarity	NPD6335	Approved
0.65	Remote Similarity	NPD5369	Approved
0.6496	Remote Similarity	NPD6053	Discontinued
0.6495	Remote Similarity	NPD6933	Approved
0.6495	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6486	Remote Similarity	NPD5223	Approved
0.6481	Remote Similarity	NPD4629	Approved
0.6481	Remote Similarity	NPD5210	Approved
0.6476	Remote Similarity	NPD4753	Phase 2
0.6475	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6475	Remote Similarity	NPD5983	Phase 2
0.6465	Remote Similarity	NPD6929	Approved
0.6458	Remote Similarity	NPD6926	Approved
0.6458	Remote Similarity	NPD6924	Approved
0.6442	Remote Similarity	NPD7750	Discontinued
0.6441	Remote Similarity	NPD8133	Approved
0.6417	Remote Similarity	NPD6317	Approved
0.641	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6408	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.64	Remote Similarity	NPD4819	Approved
0.64	Remote Similarity	NPD6931	Approved
0.64	Remote Similarity	NPD4820	Approved
0.64	Remote Similarity	NPD4252	Approved
0.64	Remote Similarity	NPD6336	Discontinued
0.64	Remote Similarity	NPD4821	Approved
0.64	Remote Similarity	NPD4822	Approved
0.64	Remote Similarity	NPD6930	Phase 2

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