NPASS Compound

Structure

CID302191 OpenBabel06191716112D 26 30 0 0 1 0 0 0 0 0999 V2000 -1.7518 0.4526 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7518 -1.2237 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4603 1.4205 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5680 0.9355 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4585 -0.4615 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4585 0.4438 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6745 -0.9141 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6745 0.8964 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7840 -1.3579 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.8105 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7840 1.3579 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.9053 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3346 -1.3470 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5680 -0.9053 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.8905 -0.4615 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1125 -0.9043 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8905 0.4438 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7840 1.3579 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.3458 0.4427 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7840 0.4526 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7840 0.4526 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.5680 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.1239 0.8855 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.6222 1.8418 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8382 -0.4839 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 20 1 0 0 0 0 2 20 1 0 0 0 0 3 21 1 0 0 0 0 5 6 2 0 0 0 0 5 7 1 0 0 0 0 6 8 1 0 0 0 0 7 15 2 0 0 0 0 8 17 2 0 0 0 0 9 12 1 0 0 0 0 9 14 1 0 0 0 0 10 11 1 0 0 0 0 10 18 1 0 0 0 0 11 21 1 0 0 0 0 12 23 1 0 0 0 0 13 14 1 0 0 0 0 13 16 1 0 0 0 0 14 22 1 6 0 0 0 15 16 1 0 0 0 0 15 17 1 0 0 0 0 16 19 2 0 0 0 0 17 24 1 0 0 0 0 18 20 1 0 0 0 0 18 25 1 6 0 0 0 19 22 1 0 0 0 0 19 24 1 0 0 0 0 20 23 1 0 0 0 0 21 22 1 6 0 0 0 22 4 1 6 0 0 0 23 21 1 6 0 0 0 23 26 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	353.24
Volume:	381.613
LogP:	3.865
LogD:	3.201
LogS:	-4.499
# Rotatable Bonds:	0
TPSA:	56.25
# H-Bond Aceptor:	3
# H-Bond Donor:	3
# Rings:	5
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.661
Synthetic Accessibility Score:	4.236
Fsp3:	0.652
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.78
MDCK Permeability:	2.1799025489599444e-05
Pgp-inhibitor:	0.088
Pgp-substrate:	0.951
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.026
30% Bioavailability (F30%):	0.165

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.729
Plasma Protein Binding (PPB):	65.9992446899414%
Volume Distribution (VD):	1.689
Pgp-substrate:	16.851037979125977%

ADMET: Metabolism

CYP1A2-inhibitor:	0.781
CYP1A2-substrate:	0.766
CYP2C19-inhibitor:	0.874
CYP2C19-substrate:	0.834
CYP2C9-inhibitor:	0.594
CYP2C9-substrate:	0.844
CYP2D6-inhibitor:	0.463
CYP2D6-substrate:	0.688
CYP3A4-inhibitor:	0.801
CYP3A4-substrate:	0.755

ADMET: Excretion

Clearance (CL):	10.938
Half-life (T1/2):	0.083

ADMET: Toxicity

hERG Blockers:	0.559
Human Hepatotoxicity (H-HT):	0.286
Drug-inuced Liver Injury (DILI):	0.035
AMES Toxicity:	0.019
Rat Oral Acute Toxicity:	0.977
Maximum Recommended Daily Dose:	0.966
Skin Sensitization:	0.317
Carcinogencity:	0.899
Eye Corrosion:	0.011
Eye Irritation:	0.089
Respiratory Toxicity:	0.976

Download Data

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

Natural Product: NPC302191

Natural Product ID:	NPC302191
*Common Name:**	Lecanindole D
IUPAC Name:	n.a.
Synonyms:	Lecanindole D
Standard InCHIKey:	QJRNEHJGTLWRJJ-BVYMYZFFSA-N
Standard InCHI:	InChI=1S/C23H31NO2/c1-20(2)18(25)10-11-21(3)22(4)14(9-12-23(20,21)26)13-16-15-7-5-6-8-17(15)24-19(16)22/h5-8,14,18,24-26H,9-13H2,1-4H3/t14-,18+,21+,22+,23+/m0/s1
SMILES:	CC1(C)[C@@H](CC[C@]2(C)[C@]3(C)[C@@H](CC[C@@]12O)Cc1c2ccccc2[nH]c31)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1076438
PubChem CID:	44605900
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000211] Indoles and derivatives [CHEMONTID:0002497] Indoles [CHEMONTID:0004196] 3-alkylindoles

*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
NPO5954	Petroselinum crispum	Species	Apiaceae	Eukaryota	n.a.	callus	n.a.	PMID[10552648]
NPO5954	Petroselinum crispum	Species	Apiaceae	Eukaryota	n.a.	leaf	n.a.	PMID[18214349]
NPO33606	Verticillium lecanii 6144	Species		Eukaryota	n.a.	Dominican Republic	n.a.	PMID[19863083]
NPO5954	Petroselinum crispum	Species	Apiaceae	Eukaryota	n.a.	seed	n.a.	PMID[21049975]
NPO5954	Petroselinum crispum	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21800857]
NPO8234	Vernonia galamensis	Species	Asteraceae	Eukaryota	n.a.	seed	n.a.	PMID[9930408]
NPO5954	Petroselinum crispum	Species	Apiaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO5954	Petroselinum crispum	Species	Apiaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO5954	Petroselinum crispum	Species	Apiaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO5954	Petroselinum crispum	Species	Apiaceae	Eukaryota	Plant	n.a.	n.a.	Database[FooDB]
NPO5954	Petroselinum crispum	Species	Apiaceae	Eukaryota	Root	n.a.	n.a.	Database[FooDB]
NPO5954	Petroselinum crispum	Species	Apiaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO5954	Petroselinum crispum	Species	Apiaceae	Eukaryota	Shoot	n.a.	n.a.	Database[FooDB]
NPO5954	Petroselinum crispum	Species	Apiaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO5954	Petroselinum crispum	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9455	Uncaria orientalis	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5954	Petroselinum crispum	Species	Apiaceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO9455	Uncaria orientalis	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8620	Caesalpinia major	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5954	Petroselinum crispum	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5954	Petroselinum crispum	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO5540	Amorpha canescens	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6292	Teucrium brevifolium	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5832	Acacia nelsonii	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4321	Siphula ceratites	Species	Icmadophilaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8620	Caesalpinia major	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24536	Senecio cylindricus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5954	Petroselinum crispum	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9330	Odinia antillensis	Species	Odiniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2389	Pinus japonica	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8234	Vernonia galamensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3668	Kalanchoe delagoensis	Species	Crassulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4875	Ugni molinae	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4072	Anacyclus radiatus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8771	Heterodermia dissecta	Species	Physciaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7188	Zieria granulata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9072	Bolocera tuediae	Species	Actiniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9455	Uncaria orientalis	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8009	Arctotis venusta	Species	Asteraceae	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
EC50	2
IC50	7
Others	9

Activity Type	# Activity
Individual Protein	18

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT542	Individual Protein	Progesterone receptor	Homo sapiens	EC50	=	1.1	nM	PMID[531668]
NPT542	Individual Protein	Progesterone receptor	Homo sapiens	Efficacy	=	68.0	%	PMID[531668]
NPT542	Individual Protein	Progesterone receptor	Homo sapiens	IC50	=	57.3	nM	PMID[531668]
NPT542	Individual Protein	Progesterone receptor	Homo sapiens	IC50	=	5.5	nM	PMID[531668]
NPT542	Individual Protein	Progesterone receptor	Homo sapiens	Ratio IC50	=	10.0	n.a.	PMID[531668]
NPT153	Individual Protein	Androgen Receptor	Homo sapiens	IC50	>	10000.0	nM	PMID[531668]
NPT153	Individual Protein	Androgen Receptor	Homo sapiens	Activity	=	41.0	%	PMID[531668]
NPT249	Individual Protein	Glucocorticoid receptor	Homo sapiens	IC50	>	1000.0	nM	PMID[531668]
NPT249	Individual Protein	Glucocorticoid receptor	Homo sapiens	Activity	=	58.0	%	PMID[531668]
NPT541	Individual Protein	Mineralocorticoid receptor	Homo sapiens	IC50	>	3000000.0	nM	PMID[531668]
NPT541	Individual Protein	Mineralocorticoid receptor	Homo sapiens	Activity	=	82.0	%	PMID[531668]
NPT108	Individual Protein	Estrogen receptor alpha	Homo sapiens	EC50	>	10000.0	nM	PMID[531668]
NPT108	Individual Protein	Estrogen receptor alpha	Homo sapiens	Activity	=	35.0	%	PMID[531668]
NPT108	Individual Protein	Estrogen receptor alpha	Homo sapiens	IC50	>	10000.0	nM	PMID[531668]
NPT108	Individual Protein	Estrogen receptor alpha	Homo sapiens	Activity	=	19.0	%	PMID[531668]
NPT248	Individual Protein	Estrogen receptor beta	Homo sapiens	IC50	>	3000.0	nM	PMID[531668]
NPT248	Individual Protein	Estrogen receptor beta	Homo sapiens	Activity	=	64.0	%	PMID[531668]
NPT542	Individual Protein	Progesterone receptor	Homo sapiens	Ratio EC50	=	10.0	n.a.	PMID[531668]

☑ 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 NPC302191 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	365
0.1-0.2	1561
0.2-0.3	5915
0.3-0.4	22721
0.4-0.5	7999
0.5-0.6	2447
0.6-0.7	1377
0.7-0.8	259
0.8-0.85	28
0.85-0.9	18
0.9-0.95	6
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9506	High Similarity	NPC97525
0.9455	High Similarity	NPC198339
0.9235	High Similarity	NPC119700
0.9172	High Similarity	NPC165201
0.9086	High Similarity	NPC231342
0.8908	High Similarity	NPC206967
0.8855	High Similarity	NPC154293
0.8851	High Similarity	NPC34271
0.8844	High Similarity	NPC99428
0.8824	High Similarity	NPC6093
0.8555	High Similarity	NPC300688
0.8541	High Similarity	NPC18661
0.8474	Intermediate Similarity	NPC471284
0.8466	Intermediate Similarity	NPC235900
0.8462	Intermediate Similarity	NPC473747
0.8453	Intermediate Similarity	NPC205403
0.837	Intermediate Similarity	NPC475151
0.8333	Intermediate Similarity	NPC151939
0.829	Intermediate Similarity	NPC96131
0.828	Intermediate Similarity	NPC123019
0.8197	Intermediate Similarity	NPC85066
0.8197	Intermediate Similarity	NPC181502
0.8168	Intermediate Similarity	NPC475165
0.8156	Intermediate Similarity	NPC476319
0.8138	Intermediate Similarity	NPC477135
0.8125	Intermediate Similarity	NPC250129
0.8092	Intermediate Similarity	NPC201700
0.8071	Intermediate Similarity	NPC61813
0.8045	Intermediate Similarity	NPC19679
0.7969	Intermediate Similarity	NPC61637
0.7955	Intermediate Similarity	NPC34508
0.7898	Intermediate Similarity	NPC126492
0.7877	Intermediate Similarity	NPC270009
0.7865	Intermediate Similarity	NPC187456
0.7857	Intermediate Similarity	NPC473547
0.7836	Intermediate Similarity	NPC285469
0.7817	Intermediate Similarity	NPC160527
0.7817	Intermediate Similarity	NPC473650
0.7817	Intermediate Similarity	NPC97388
0.7809	Intermediate Similarity	NPC189812
0.7809	Intermediate Similarity	NPC329688
0.7809	Intermediate Similarity	NPC472586
0.7783	Intermediate Similarity	NPC475424
0.7783	Intermediate Similarity	NPC79107
0.7778	Intermediate Similarity	NPC470507
0.7778	Intermediate Similarity	NPC472443
0.7771	Intermediate Similarity	NPC470508
0.7759	Intermediate Similarity	NPC16667
0.7747	Intermediate Similarity	NPC472108
0.7747	Intermediate Similarity	NPC139291
0.7722	Intermediate Similarity	NPC293472
0.7718	Intermediate Similarity	NPC282033
0.7714	Intermediate Similarity	NPC40779
0.7692	Intermediate Similarity	NPC192270
0.7674	Intermediate Similarity	NPC207726
0.7665	Intermediate Similarity	NPC311330
0.765	Intermediate Similarity	NPC472444
0.7644	Intermediate Similarity	NPC476175
0.764	Intermediate Similarity	NPC280548
0.7624	Intermediate Similarity	NPC470874
0.7619	Intermediate Similarity	NPC242556
0.7614	Intermediate Similarity	NPC311276
0.7604	Intermediate Similarity	NPC49196
0.7604	Intermediate Similarity	NPC79129
0.7604	Intermediate Similarity	NPC195461
0.7604	Intermediate Similarity	NPC313985
0.7604	Intermediate Similarity	NPC81654
0.7604	Intermediate Similarity	NPC249150
0.7594	Intermediate Similarity	NPC95783
0.7592	Intermediate Similarity	NPC50503
0.7588	Intermediate Similarity	NPC477134
0.7586	Intermediate Similarity	NPC469762
0.7584	Intermediate Similarity	NPC317430
0.7582	Intermediate Similarity	NPC213468
0.7576	Intermediate Similarity	NPC204303
0.7574	Intermediate Similarity	NPC475476
0.7574	Intermediate Similarity	NPC242446
0.7572	Intermediate Similarity	NPC471458
0.7563	Intermediate Similarity	NPC284102
0.7556	Intermediate Similarity	NPC472123
0.7544	Intermediate Similarity	NPC37548
0.7544	Intermediate Similarity	NPC124005
0.7543	Intermediate Similarity	NPC67056
0.754	Intermediate Similarity	NPC46413
0.7529	Intermediate Similarity	NPC469785
0.7525	Intermediate Similarity	NPC234999
0.75	Intermediate Similarity	NPC477041
0.75	Intermediate Similarity	NPC477044
0.75	Intermediate Similarity	NPC473320
0.7485	Intermediate Similarity	NPC475450
0.7477	Intermediate Similarity	NPC94541
0.7477	Intermediate Similarity	NPC470843
0.7473	Intermediate Similarity	NPC288785
0.7471	Intermediate Similarity	NPC38736
0.7461	Intermediate Similarity	NPC32200
0.7461	Intermediate Similarity	NPC477045
0.7459	Intermediate Similarity	NPC472110
0.7459	Intermediate Similarity	NPC472109
0.7442	Intermediate Similarity	NPC187951
0.7439	Intermediate Similarity	NPC473930
0.743	Intermediate Similarity	NPC54988
0.743	Intermediate Similarity	NPC49954
0.743	Intermediate Similarity	NPC474561
0.7429	Intermediate Similarity	NPC184476
0.7423	Intermediate Similarity	NPC475428
0.7421	Intermediate Similarity	NPC67551
0.7419	Intermediate Similarity	NPC472294
0.7416	Intermediate Similarity	NPC471634
0.7416	Intermediate Similarity	NPC473806
0.7414	Intermediate Similarity	NPC73952
0.7414	Intermediate Similarity	NPC469786
0.7414	Intermediate Similarity	NPC469765
0.7414	Intermediate Similarity	NPC25008
0.7414	Intermediate Similarity	NPC259644
0.7414	Intermediate Similarity	NPC469760
0.7414	Intermediate Similarity	NPC469763
0.7404	Intermediate Similarity	NPC470873
0.7404	Intermediate Similarity	NPC249342
0.7399	Intermediate Similarity	NPC33421
0.7389	Intermediate Similarity	NPC63751
0.7381	Intermediate Similarity	NPC312092
0.7371	Intermediate Similarity	NPC212376
0.7371	Intermediate Similarity	NPC211572
0.7371	Intermediate Similarity	NPC70922
0.7371	Intermediate Similarity	NPC80597
0.7371	Intermediate Similarity	NPC75540
0.7363	Intermediate Similarity	NPC475778
0.7362	Intermediate Similarity	NPC473587
0.736	Intermediate Similarity	NPC477043
0.7354	Intermediate Similarity	NPC128751
0.735	Intermediate Similarity	NPC475422
0.7345	Intermediate Similarity	NPC230869
0.734	Intermediate Similarity	NPC204491
0.734	Intermediate Similarity	NPC203614
0.7337	Intermediate Similarity	NPC68354
0.7337	Intermediate Similarity	NPC87755
0.7333	Intermediate Similarity	NPC160105
0.7326	Intermediate Similarity	NPC129042
0.7322	Intermediate Similarity	NPC37423
0.7322	Intermediate Similarity	NPC275305
0.7316	Intermediate Similarity	NPC106833
0.7316	Intermediate Similarity	NPC469497
0.731	Intermediate Similarity	NPC98715
0.7308	Intermediate Similarity	NPC141428
0.7306	Intermediate Similarity	NPC11445
0.7302	Intermediate Similarity	NPC317030
0.7301	Intermediate Similarity	NPC473762
0.7297	Intermediate Similarity	NPC176199
0.7297	Intermediate Similarity	NPC215795
0.7296	Intermediate Similarity	NPC300183
0.7284	Intermediate Similarity	NPC250361
0.7283	Intermediate Similarity	NPC472122
0.7283	Intermediate Similarity	NPC24594
0.7273	Intermediate Similarity	NPC179365
0.7273	Intermediate Similarity	NPC112547
0.7273	Intermediate Similarity	NPC163055
0.7273	Intermediate Similarity	NPC267926
0.7268	Intermediate Similarity	NPC313791
0.7263	Intermediate Similarity	NPC282231
0.7263	Intermediate Similarity	NPC246700
0.726	Intermediate Similarity	NPC147446
0.726	Intermediate Similarity	NPC266192
0.7254	Intermediate Similarity	NPC157828
0.7254	Intermediate Similarity	NPC195239
0.725	Intermediate Similarity	NPC258062
0.725	Intermediate Similarity	NPC127677
0.7247	Intermediate Similarity	NPC41257
0.7243	Intermediate Similarity	NPC59269
0.7243	Intermediate Similarity	NPC326575
0.7238	Intermediate Similarity	NPC57690
0.7234	Intermediate Similarity	NPC190007
0.7225	Intermediate Similarity	NPC469501
0.7225	Intermediate Similarity	NPC212799
0.7225	Intermediate Similarity	NPC469470
0.7222	Intermediate Similarity	NPC194640
0.7222	Intermediate Similarity	NPC472587
0.7222	Intermediate Similarity	NPC102423
0.7219	Intermediate Similarity	NPC314394
0.7219	Intermediate Similarity	NPC233936
0.7217	Intermediate Similarity	NPC290529
0.7216	Intermediate Similarity	NPC200743
0.7213	Intermediate Similarity	NPC6982
0.7211	Intermediate Similarity	NPC204565
0.7207	Intermediate Similarity	NPC279918
0.7204	Intermediate Similarity	NPC88363
0.7204	Intermediate Similarity	NPC133261
0.7202	Intermediate Similarity	NPC474177
0.72	Intermediate Similarity	NPC46225
0.72	Intermediate Similarity	NPC225821
0.7196	Intermediate Similarity	NPC163421
0.7196	Intermediate Similarity	NPC94943
0.7196	Intermediate Similarity	NPC473189
0.7196	Intermediate Similarity	NPC188387
0.7191	Intermediate Similarity	NPC286427
0.7191	Intermediate Similarity	NPC299594
0.7179	Intermediate Similarity	NPC153042
0.7179	Intermediate Similarity	NPC229332
0.7179	Intermediate Similarity	NPC232130
0.7174	Intermediate Similarity	NPC314603
0.7173	Intermediate Similarity	NPC173028

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 NPC302191 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	238
0.1-0.2	565
0.2-0.3	647
0.3-0.4	2040
0.4-0.5	3360
0.5-0.6	1823
0.6-0.7	443
0.7-0.8	34
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.767	Intermediate Similarity	NPD5744	Clinical (unspecified phase)
0.7604	Intermediate Similarity	NPD4600	Approved
0.7604	Intermediate Similarity	NPD4601	Approved
0.746	Intermediate Similarity	NPD6630	Clinical (unspecified phase)
0.7446	Intermediate Similarity	NPD8464	Clinical (unspecified phase)
0.7399	Intermediate Similarity	NPD4462	Approved
0.7399	Intermediate Similarity	NPD4463	Approved
0.7396	Intermediate Similarity	NPD1592	Phase 3
0.7391	Intermediate Similarity	NPD4079	Approved
0.7391	Intermediate Similarity	NPD4076	Approved
0.7389	Intermediate Similarity	NPD5021	Discontinued
0.736	Intermediate Similarity	NPD972	Clinical (unspecified phase)
0.7351	Intermediate Similarity	NPD6595	Phase 3
0.7337	Intermediate Similarity	NPD3505	Approved
0.7337	Intermediate Similarity	NPD3506	Approved
0.7302	Intermediate Similarity	NPD8431	Approved
0.7268	Intermediate Similarity	NPD4112	Clinical (unspecified phase)
0.7268	Intermediate Similarity	NPD5003	Discontinued
0.7253	Intermediate Similarity	NPD1325	Approved
0.7253	Intermediate Similarity	NPD1326	Approved
0.7253	Intermediate Similarity	NPD4184	Clinical (unspecified phase)
0.7232	Intermediate Similarity	NPD6026	Approved
0.7209	Intermediate Similarity	NPD5254	Discontinued
0.7204	Intermediate Similarity	NPD8386	Phase 2
0.7188	Intermediate Similarity	NPD5913	Phase 3
0.7188	Intermediate Similarity	NPD5912	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD2144	Approved
0.7151	Intermediate Similarity	NPD6203	Clinical (unspecified phase)
0.715	Intermediate Similarity	NPD7958	Clinical (unspecified phase)
0.715	Intermediate Similarity	NPD7957	Phase 1
0.7143	Intermediate Similarity	NPD5936	Approved
0.7143	Intermediate Similarity	NPD5939	Approved
0.7143	Intermediate Similarity	NPD4880	Discontinued
0.7135	Intermediate Similarity	NPD3943	Clinical (unspecified phase)
0.7128	Intermediate Similarity	NPD3038	Discontinued
0.7105	Intermediate Similarity	NPD6610	Clinical (unspecified phase)
0.7104	Intermediate Similarity	NPD5069	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD2380	Approved
0.7097	Intermediate Similarity	NPD2382	Approved
0.7097	Intermediate Similarity	NPD2381	Approved
0.709	Intermediate Similarity	NPD5596	Phase 2
0.7081	Intermediate Similarity	NPD7418	Discontinued
0.7079	Intermediate Similarity	NPD7947	Clinical (unspecified phase)
0.7065	Intermediate Similarity	NPD7474	Suspended
0.7062	Intermediate Similarity	NPD6158	Phase 2
0.7062	Intermediate Similarity	NPD6476	Clinical (unspecified phase)
0.7043	Intermediate Similarity	NPD5065	Approved
0.7033	Intermediate Similarity	NPD5140	Approved
0.7033	Intermediate Similarity	NPD5138	Approved
0.7011	Intermediate Similarity	NPD4638	Approved
0.7011	Intermediate Similarity	NPD2844	Phase 3
0.7011	Intermediate Similarity	NPD4639	Approved
0.7011	Intermediate Similarity	NPD4640	Approved
0.7005	Intermediate Similarity	NPD6375	Clinical (unspecified phase)
0.6989	Remote Similarity	NPD43	Approved
0.6989	Remote Similarity	NPD6182	Approved
0.6989	Remote Similarity	NPD6183	Clinical (unspecified phase)
0.6984	Remote Similarity	NPD5899	Approved
0.6984	Remote Similarity	NPD5898	Approved
0.6984	Remote Similarity	NPD5897	Approved
0.6971	Remote Similarity	NPD5164	Discontinued
0.6959	Remote Similarity	NPD1262	Discovery
0.6959	Remote Similarity	NPD4499	Approved
0.6959	Remote Similarity	NPD2564	Approved
0.6959	Remote Similarity	NPD2565	Phase 2
0.6957	Remote Similarity	NPD7707	Approved
0.694	Remote Similarity	NPD3323	Discontinued
0.6931	Remote Similarity	NPD3417	Phase 1
0.6911	Remote Similarity	NPD2092	Phase 2
0.6911	Remote Similarity	NPD2095	Phase 2
0.6911	Remote Similarity	NPD2094	Phase 2
0.6911	Remote Similarity	NPD5728	Clinical (unspecified phase)
0.6911	Remote Similarity	NPD5522	Clinical (unspecified phase)
0.691	Remote Similarity	NPD2172	Phase 1
0.691	Remote Similarity	NPD3835	Phase 3
0.691	Remote Similarity	NPD3833	Phase 3
0.6907	Remote Similarity	NPD8110	Clinical (unspecified phase)
0.6906	Remote Similarity	NPD4671	Clinical (unspecified phase)
0.6906	Remote Similarity	NPD4669	Clinical (unspecified phase)
0.6906	Remote Similarity	NPD4670	Clinical (unspecified phase)
0.6888	Remote Similarity	NPD6619	Phase 3
0.6878	Remote Similarity	NPD4181	Approved
0.6875	Remote Similarity	NPD2096	Phase 2
0.6875	Remote Similarity	NPD2091	Phase 2
0.6875	Remote Similarity	NPD8112	Clinical (unspecified phase)
0.6868	Remote Similarity	NPD1554	Clinical (unspecified phase)
0.6866	Remote Similarity	NPD4511	Phase 1
0.6856	Remote Similarity	NPD3486	Clinical (unspecified phase)
0.6856	Remote Similarity	NPD6141	Clinical (unspecified phase)
0.6853	Remote Similarity	NPD5575	Clinical (unspecified phase)
0.6851	Remote Similarity	NPD2580	Discontinued
0.685	Remote Similarity	NPD2177	Approved
0.685	Remote Similarity	NPD2176	Approved
0.685	Remote Similarity	NPD2175	Phase 3
0.6842	Remote Similarity	NPD6555	Clinical (unspecified phase)
0.6834	Remote Similarity	NPD7948	Phase 1
0.6825	Remote Similarity	NPD5501	Discontinued
0.6825	Remote Similarity	NPD749	Clinical (unspecified phase)
0.68	Remote Similarity	NPD1722	Approved
0.68	Remote Similarity	NPD53	Approved
0.68	Remote Similarity	NPD7777	Approved
0.68	Remote Similarity	NPD7778	Approved
0.6796	Remote Similarity	NPD2125	Clinical (unspecified phase)
0.6784	Remote Similarity	NPD6503	Clinical (unspecified phase)
0.6784	Remote Similarity	NPD7935	Phase 2
0.6782	Remote Similarity	NPD786	Approved
0.678	Remote Similarity	NPD8322	Phase 2
0.6778	Remote Similarity	NPD2882	Phase 1
0.6772	Remote Similarity	NPD482	Approved
0.6772	Remote Similarity	NPD6492	Phase 2
0.6772	Remote Similarity	NPD4128	Approved
0.6766	Remote Similarity	NPD4118	Clinical (unspecified phase)
0.6761	Remote Similarity	NPD4637	Clinical (unspecified phase)
0.6761	Remote Similarity	NPD3525	Discontinued
0.676	Remote Similarity	NPD4374	Clinical (unspecified phase)
0.676	Remote Similarity	NPD3100	Discontinued
0.6757	Remote Similarity	NPD6635	Approved
0.6755	Remote Similarity	NPD6739	Clinical (unspecified phase)
0.6753	Remote Similarity	NPD6344	Clinical (unspecified phase)
0.6737	Remote Similarity	NPD4075	Phase 2
0.6736	Remote Similarity	NPD4345	Clinical (unspecified phase)
0.6735	Remote Similarity	NPD1534	Approved
0.6734	Remote Similarity	NPD7944	Discontinued
0.6733	Remote Similarity	NPD4500	Approved
0.6733	Remote Similarity	NPD4501	Approved
0.6732	Remote Similarity	NPD3003	Approved
0.6731	Remote Similarity	NPD6220	Phase 3
0.6716	Remote Similarity	NPD2920	Discontinued
0.6705	Remote Similarity	NPD198	Clinical (unspecified phase)
0.6704	Remote Similarity	NPD4702	Approved
0.6704	Remote Similarity	NPD4703	Approved
0.6702	Remote Similarity	NPD8123	Approved
0.6702	Remote Similarity	NPD6159	Phase 2
0.6702	Remote Similarity	NPD8122	Approved
0.6701	Remote Similarity	NPD6281	Approved
0.67	Remote Similarity	NPD6449	Clinical (unspecified phase)
0.6686	Remote Similarity	NPD3385	Approved
0.6684	Remote Similarity	NPD4383	Clinical (unspecified phase)
0.6684	Remote Similarity	NPD3961	Discontinued
0.6683	Remote Similarity	NPD5426	Phase 3
0.6683	Remote Similarity	NPD1038	Approved
0.6683	Remote Similarity	NPD8395	Approved
0.6683	Remote Similarity	NPD8396	Approved
0.6667	Remote Similarity	NPD3609	Approved
0.6667	Remote Similarity	NPD3610	Approved
0.6667	Remote Similarity	NPD5721	Clinical (unspecified phase)
0.6651	Remote Similarity	NPD6995	Phase 1
0.665	Remote Similarity	NPD3791	Clinical (unspecified phase)
0.6648	Remote Similarity	NPD1528	Clinical (unspecified phase)
0.6648	Remote Similarity	NPD1683	Approved
0.6635	Remote Similarity	NPD5902	Approved
0.6635	Remote Similarity	NPD5903	Approved
0.6634	Remote Similarity	NPD6176	Phase 1
0.6634	Remote Similarity	NPD8072	Approved
0.6634	Remote Similarity	NPD3230	Clinical (unspecified phase)
0.6632	Remote Similarity	NPD5473	Discontinued
0.6631	Remote Similarity	NPD4550	Clinical (unspecified phase)
0.6618	Remote Similarity	NPD8493	Clinical (unspecified phase)
0.6618	Remote Similarity	NPD6290	Phase 2
0.6615	Remote Similarity	NPD5083	Clinical (unspecified phase)
0.6613	Remote Similarity	NPD1685	Approved
0.6613	Remote Similarity	NPD1684	Approved
0.6612	Remote Similarity	NPD5257	Clinical (unspecified phase)
0.661	Remote Similarity	NPD3834	Clinical (unspecified phase)
0.6609	Remote Similarity	NPD3864	Clinical (unspecified phase)
0.6601	Remote Similarity	NPD7621	Clinical (unspecified phase)
0.6588	Remote Similarity	NPD7276	Approved
0.6588	Remote Similarity	NPD7277	Approved
0.6588	Remote Similarity	NPD5352	Clinical (unspecified phase)
0.6588	Remote Similarity	NPD8094	Discontinued
0.6587	Remote Similarity	NPD2916	Discontinued
0.6585	Remote Similarity	NPD6975	Discontinued
0.6585	Remote Similarity	NPD7187	Phase 2
0.6585	Remote Similarity	NPD8073	Approved
0.6579	Remote Similarity	NPD5934	Clinical (unspecified phase)
0.6571	Remote Similarity	NPD4502	Phase 2
0.6566	Remote Similarity	NPD7234	Approved
0.6566	Remote Similarity	NPD7233	Approved
0.6561	Remote Similarity	NPD2641	Approved
0.6561	Remote Similarity	NPD2640	Approved
0.6561	Remote Similarity	NPD4779	Clinical (unspecified phase)
0.6557	Remote Similarity	NPD2837	Discontinued
0.655	Remote Similarity	NPD3654	Approved
0.6545	Remote Similarity	NPD750	Phase 2
0.6541	Remote Similarity	NPD4326	Phase 2
0.654	Remote Similarity	NPD8093	Discontinued
0.6537	Remote Similarity	NPD6145	Phase 1
0.6531	Remote Similarity	NPD4957	Phase 2
0.6524	Remote Similarity	NPD7825	Clinical (unspecified phase)
0.6524	Remote Similarity	NPD7998	Clinical (unspecified phase)
0.6524	Remote Similarity	NPD7809	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD8115	Approved
0.6522	Remote Similarity	NPD8114	Approved
0.6522	Remote Similarity	NPD8272	Phase 2
0.652	Remote Similarity	NPD1768	Approved
0.652	Remote Similarity	NPD6661	Clinical (unspecified phase)
0.6517	Remote Similarity	NPD1304	Clinical (unspecified phase)
0.6515	Remote Similarity	NPD3002	Clinical (unspecified phase)
0.6515	Remote Similarity	NPD5590	Clinical (unspecified phase)
0.6515	Remote Similarity	NPD2383	Phase 1

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