NPASS Compound

Structure

CID158148 OpenBabel06191715532D 22 26 0 0 1 0 0 0 0 0999 V2000 1.3731 -2.5006 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9448 -0.4642 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5842 -0.0046 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5147 -1.9520 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2820 -1.2821 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5147 -0.1135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0002 -2.0654 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2951 -1.0326 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7254 -1.0328 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7186 -1.4924 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8103 -1.0328 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.7186 -0.5731 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3108 -1.4924 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3108 -0.5731 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1321 -1.0826 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8962 -0.2044 0.0000 C 0 0 1 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 -0.8964 -1.8610 0.0000 N 0 0 3 0 0 0 0 0 0 0 0 0 -1.4323 0.4681 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5154 -1.6042 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.1851 -1.7765 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.1851 -0.2891 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 20 1 0 0 0 0 2 3 2 0 0 0 0 2 11 1 0 0 0 0 4 10 2 0 0 0 0 4 13 1 0 0 0 0 5 11 1 0 0 0 0 5 15 1 0 0 0 0 6 12 2 0 0 0 0 6 14 1 0 0 0 0 7 10 1 0 0 0 0 7 18 1 0 0 0 0 8 16 1 0 0 0 0 8 18 1 0 0 0 0 9 21 1 0 0 0 0 9 22 1 0 0 0 0 10 12 1 0 0 0 0 11 20 1 6 0 0 0 12 17 1 0 0 0 0 13 14 2 0 0 0 0 13 21 1 0 0 0 0 14 22 1 0 0 0 0 15 17 1 6 0 0 0 15 18 1 0 0 0 0 16 17 1 6 0 0 0 16 19 1 0 0 0 0 17 3 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	301.13
Volume:	295.418
LogP:	1.197
LogD:	0.971
LogS:	-2.201
# Rotatable Bonds:	1
TPSA:	51.16
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	5
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.79
Synthetic Accessibility Score:	5.217
Fsp3:	0.529
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:	-4.881
MDCK Permeability:	2.9016788175795227e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.981
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.833
30% Bioavailability (F30%):	0.326

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.996
Plasma Protein Binding (PPB):	58.56382751464844%
Volume Distribution (VD):	1.884
Pgp-substrate:	35.6910514831543%

ADMET: Metabolism

CYP1A2-inhibitor:	0.365
CYP1A2-substrate:	0.569
CYP2C19-inhibitor:	0.152
CYP2C19-substrate:	0.839
CYP2C9-inhibitor:	0.03
CYP2C9-substrate:	0.397
CYP2D6-inhibitor:	0.941
CYP2D6-substrate:	0.765
CYP3A4-inhibitor:	0.892
CYP3A4-substrate:	0.786

ADMET: Excretion

Clearance (CL):	10.311
Half-life (T1/2):	0.534

ADMET: Toxicity

hERG Blockers:	0.283
Human Hepatotoxicity (H-HT):	0.287
Drug-inuced Liver Injury (DILI):	0.083
AMES Toxicity:	0.307
Rat Oral Acute Toxicity:	0.58
Maximum Recommended Daily Dose:	0.97
Skin Sensitization:	0.128
Carcinogencity:	0.752
Eye Corrosion:	0.004
Eye Irritation:	0.011
Respiratory Toxicity:	0.947

Download Data

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

Natural Product: NPC158148

Natural Product ID:	NPC158148
*Common Name:**	YGPRSGKVLATIHT-SPOWBLRKSA-N
IUPAC Name:	n.a.
Synonyms:	(+)-Crinamine
Standard InCHIKey:	YGPRSGKVLATIHT-SPOWBLRKSA-N
Standard InCHI:	InChI=1S/C17H19NO4/c1-20-11-2-3-17-12-6-14-13(21-9-22-14)4-10(12)7-18(8-16(17)19)15(17)5-11/h2-4,6,11,15-16,19H,5,7-9H2,1H3/t11-,15-,16-,17-/m0/s1
SMILES:	CO[C@H]1C=C[C@]23c4cc5c(cc4CN(C[C@@H]3O)[C@H]2C1)OCO5
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL516991
PubChem CID:	73620
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids and derivatives [CHEMONTID:0001775] Amaryllidaceae alkaloids [CHEMONTID:0004123] Crinine- and Haemanthamine-type amaryllidaceae alkaloids

*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
NPO23263	Crinum yemense	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15270564]
NPO22157	Datura wrightii	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23252848]
NPO22317	Crinum amabile	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8229016]
NPO3630	Crotalaria crispata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO22317	Crinum amabile	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9927	Crinum asiaticum	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO22054	Cinchona officinalis	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO22054	Cinchona officinalis	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9927	Crinum asiaticum	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3630	Crotalaria crispata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1383.1	Murraya paniculata var. omphalocarpa	Varieties	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22317	Crinum amabile	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9927	Crinum asiaticum	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1412	Artemisia juncea	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22009	Lupinus holosericeus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19776	Hesperocyparis arizonica	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23263	Crinum yemense	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9485	Haplopappus deserticola	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1383.1	Murraya paniculata var. omphalocarpa	Varieties	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9144	Atriplex parvifolia	Species	Chenopodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11000	Eupatorium laevigatum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13659	Helichrysum asperum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23036	Angelica hirsutiflora	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11473	Viburnum lantana	Species	Adoxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22317	Crinum amabile	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18476	Lophopetalum toxicum	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1828	Searsia leptodictya	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21442	Elaeocarpus sphaericus	Species	Elaeocarpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20170	Anthoceros punctatus	Species	Anthocerotaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3630	Crotalaria crispata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23120	Clausena suffruticosa	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22157	Datura wrightii	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22054	Cinchona officinalis	Species	Rubiaceae	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	14
IC50	2
Others	12

Activity Type	# Activity
Cell Line	7
NON-MOLECULAR	5
Organism	3
Others	13

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT147	Cell Line	SK-MEL-2	Homo sapiens	ED50	=	5.0	ug ml-1	PMID[490400]
NPT91	Cell Line	KB	Homo sapiens	ED50	=	1.0	ug ml-1	PMID[490400]
NPT168	Cell Line	P388	Mus musculus	ED50	=	0.7	ug ml-1	PMID[490400]
NPT762	Cell Line	A-431	Homo sapiens	ED50	=	6.9	ug ml-1	PMID[490400]
NPT858	Cell Line	LNCaP	Homo sapiens	ED50	=	1.5	ug ml-1	PMID[490400]
NPT133	Cell Line	ZR-75-1	Homo sapiens	ED50	=	0.8	ug ml-1	PMID[490400]
NPT453	Cell Line	HT-1080	Homo sapiens	ED50	=	1.3	ug ml-1	PMID[490400]
NPT2	Others	Unspecified		Inhibition	=	8.1	%	PMID[490399]
NPT27	Others	Unspecified		Activity	=	100.1	%	PMID[490399]
NPT2	Others	Unspecified		Inhibition	=	7.8	%	PMID[490399]
NPT27	Others	Unspecified		Activity	=	100.6	%	PMID[490399]
NPT2	Others	Unspecified		Inhibition	=	30.2	%	PMID[490399]
NPT2	Others	Unspecified		Inhibition	=	65.2	%	PMID[490399]
NPT27	Others	Unspecified		Activity	=	100.5	%	PMID[490399]
NPT2	Others	Unspecified		Inhibition	=	86.1	%	PMID[490399]
NPT27	Others	Unspecified		Activity	=	84.5	%	PMID[490399]
NPT2	Others	Unspecified		IC50	=	1800.0	nM	PMID[490399]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	ED50	=	1.4	ug ml-1	PMID[490400]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	ED50	=	1.0	ug ml-1	PMID[490400]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	ED50	=	0.6	ug ml-1	PMID[490400]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	ED50	=	0.9	ug ml-1	PMID[490400]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	ED50	=	2180.0	ug ml-1	PMID[490400]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	ED50	=	2520.0	ug ml-1	PMID[490400]
NPT2	Others	Unspecified		Ratio ED50	=	0.4	n.a.	PMID[490400]
NPT992	Organism	Entamoeba histolytica	Entamoeba histolytica	IC50	=	0.53	ug.mL-1	PMID[490401]

☑ 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 NPC158148 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	263
0.1-0.2	1245
0.2-0.3	4113
0.3-0.4	12227
0.4-0.5	7727
0.5-0.6	12838
0.6-0.7	3387
0.7-0.8	657
0.8-0.85	142
0.85-0.9	54
0.9-0.95	31
0.95-1	13

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC266176
1.0	High Similarity	NPC82533
1.0	High Similarity	NPC290759
0.9873	High Similarity	NPC477640
0.9873	High Similarity	NPC225597
0.9873	High Similarity	NPC470739
0.9872	High Similarity	NPC58766
0.9872	High Similarity	NPC475686
0.9809	High Similarity	NPC474475
0.9688	High Similarity	NPC474470
0.9568	High Similarity	NPC244554
0.9487	High Similarity	NPC215829
0.9487	High Similarity	NPC97072
0.9434	High Similarity	NPC100566
0.9367	High Similarity	NPC218614
0.9367	High Similarity	NPC320104
0.9355	High Similarity	NPC78733
0.9317	High Similarity	NPC311991
0.9313	High Similarity	NPC181653
0.9313	High Similarity	NPC190332
0.9313	High Similarity	NPC252960
0.9308	High Similarity	NPC247972
0.9198	High Similarity	NPC75958
0.9146	High Similarity	NPC304675
0.9091	High Similarity	NPC237044
0.9085	High Similarity	NPC2314
0.9036	High Similarity	NPC474325
0.9036	High Similarity	NPC15919
0.9012	High Similarity	NPC476002
0.8982	High Similarity	NPC474745
0.8957	High Similarity	NPC57812
0.8957	High Similarity	NPC474324
0.8938	High Similarity	NPC59028
0.8938	High Similarity	NPC92191
0.8931	High Similarity	NPC147091
0.8922	High Similarity	NPC294790
0.8922	High Similarity	NPC118633
0.8922	High Similarity	NPC148693
0.8909	High Similarity	NPC65403
0.8902	High Similarity	NPC475845
0.8861	High Similarity	NPC148898
0.8848	High Similarity	NPC474708
0.8824	High Similarity	NPC474746
0.8824	High Similarity	NPC475981
0.8802	High Similarity	NPC187678
0.8772	High Similarity	NPC9867
0.8765	High Similarity	NPC205167
0.8765	High Similarity	NPC4304
0.8765	High Similarity	NPC249274
0.8726	High Similarity	NPC475959
0.8721	High Similarity	NPC230098
0.869	High Similarity	NPC49353
0.8655	High Similarity	NPC248642
0.8647	High Similarity	NPC126284
0.8625	High Similarity	NPC233029
0.8625	High Similarity	NPC223124
0.8625	High Similarity	NPC210148
0.8616	High Similarity	NPC274026
0.8614	High Similarity	NPC150879
0.8605	High Similarity	NPC156576
0.858	High Similarity	NPC234392
0.858	High Similarity	NPC31311
0.8547	High Similarity	NPC275132
0.8519	High Similarity	NPC41178
0.8519	High Similarity	NPC138487
0.8519	High Similarity	NPC216459
0.85	High Similarity	NPC223125
0.8494	Intermediate Similarity	NPC276944
0.8494	Intermediate Similarity	NPC231198
0.8494	Intermediate Similarity	NPC238530
0.8494	Intermediate Similarity	NPC232514
0.8476	Intermediate Similarity	NPC111485
0.8466	Intermediate Similarity	NPC146288
0.8439	Intermediate Similarity	NPC102760
0.8439	Intermediate Similarity	NPC233718
0.8434	Intermediate Similarity	NPC233650
0.843	Intermediate Similarity	NPC99179
0.8418	Intermediate Similarity	NPC130926
0.84	Intermediate Similarity	NPC214116
0.8395	Intermediate Similarity	NPC82285
0.8395	Intermediate Similarity	NPC133011
0.8393	Intermediate Similarity	NPC210918
0.8383	Intermediate Similarity	NPC134858
0.8364	Intermediate Similarity	NPC477080
0.8333	Intermediate Similarity	NPC24264
0.8333	Intermediate Similarity	NPC476432
0.8323	Intermediate Similarity	NPC59567
0.8313	Intermediate Similarity	NPC165797
0.8303	Intermediate Similarity	NPC315707
0.8303	Intermediate Similarity	NPC78359
0.8303	Intermediate Similarity	NPC65490
0.8303	Intermediate Similarity	NPC148014
0.8303	Intermediate Similarity	NPC40389
0.8302	Intermediate Similarity	NPC185838
0.8284	Intermediate Similarity	NPC247389
0.8284	Intermediate Similarity	NPC210140
0.828	Intermediate Similarity	NPC474915
0.828	Intermediate Similarity	NPC328750
0.828	Intermediate Similarity	NPC213206
0.828	Intermediate Similarity	NPC188163
0.8274	Intermediate Similarity	NPC16805
0.8274	Intermediate Similarity	NPC167546
0.8274	Intermediate Similarity	NPC225774
0.8274	Intermediate Similarity	NPC180306
0.8274	Intermediate Similarity	NPC302527
0.8266	Intermediate Similarity	NPC320223
0.8266	Intermediate Similarity	NPC114364
0.8261	Intermediate Similarity	NPC147390
0.8261	Intermediate Similarity	NPC135538
0.8261	Intermediate Similarity	NPC24233
0.8261	Intermediate Similarity	NPC476571
0.8261	Intermediate Similarity	NPC246587
0.8261	Intermediate Similarity	NPC428
0.8258	Intermediate Similarity	NPC7018
0.8256	Intermediate Similarity	NPC128560
0.8256	Intermediate Similarity	NPC229166
0.8256	Intermediate Similarity	NPC199465
0.8246	Intermediate Similarity	NPC57272
0.8242	Intermediate Similarity	NPC323443
0.8242	Intermediate Similarity	NPC180756
0.8235	Intermediate Similarity	NPC160570
0.8229	Intermediate Similarity	NPC476575
0.8225	Intermediate Similarity	NPC124657
0.8225	Intermediate Similarity	NPC219341
0.8217	Intermediate Similarity	NPC314682
0.8199	Intermediate Similarity	NPC179825
0.8199	Intermediate Similarity	NPC191376
0.8199	Intermediate Similarity	NPC321505
0.8199	Intermediate Similarity	NPC476151
0.8193	Intermediate Similarity	NPC129603
0.8182	Intermediate Similarity	NPC76079
0.8182	Intermediate Similarity	NPC93593
0.8176	Intermediate Similarity	NPC301189
0.8176	Intermediate Similarity	NPC298186
0.8176	Intermediate Similarity	NPC298979
0.8166	Intermediate Similarity	NPC169743
0.8156	Intermediate Similarity	NPC63152
0.8148	Intermediate Similarity	NPC37144
0.8148	Intermediate Similarity	NPC59907
0.8146	Intermediate Similarity	NPC141440
0.8144	Intermediate Similarity	NPC106786
0.8133	Intermediate Similarity	NPC37205
0.8133	Intermediate Similarity	NPC160931
0.8114	Intermediate Similarity	NPC267408
0.8111	Intermediate Similarity	NPC117717
0.8103	Intermediate Similarity	NPC283999
0.8098	Intermediate Similarity	NPC103379
0.8098	Intermediate Similarity	NPC477565
0.8095	Intermediate Similarity	NPC18402
0.8095	Intermediate Similarity	NPC477559
0.8095	Intermediate Similarity	NPC306902
0.8095	Intermediate Similarity	NPC266753
0.8095	Intermediate Similarity	NPC160298
0.8095	Intermediate Similarity	NPC232924
0.8086	Intermediate Similarity	NPC210437
0.8086	Intermediate Similarity	NPC106295
0.8086	Intermediate Similarity	NPC16107
0.8086	Intermediate Similarity	NPC476144
0.8086	Intermediate Similarity	NPC51957
0.8084	Intermediate Similarity	NPC475326
0.8081	Intermediate Similarity	NPC329911
0.8072	Intermediate Similarity	NPC127674
0.8072	Intermediate Similarity	NPC295691
0.8072	Intermediate Similarity	NPC184026
0.8072	Intermediate Similarity	NPC54379
0.8072	Intermediate Similarity	NPC278799
0.8072	Intermediate Similarity	NPC2413
0.8072	Intermediate Similarity	NPC207757
0.8072	Intermediate Similarity	NPC39701
0.8072	Intermediate Similarity	NPC276588
0.8072	Intermediate Similarity	NPC193949
0.8072	Intermediate Similarity	NPC189266
0.8072	Intermediate Similarity	NPC110416
0.8072	Intermediate Similarity	NPC204828
0.8072	Intermediate Similarity	NPC469817
0.8072	Intermediate Similarity	NPC5238
0.8072	Intermediate Similarity	NPC249797
0.8072	Intermediate Similarity	NPC172765
0.8063	Intermediate Similarity	NPC128019
0.8063	Intermediate Similarity	NPC136860
0.8063	Intermediate Similarity	NPC476567
0.8059	Intermediate Similarity	NPC76116
0.8049	Intermediate Similarity	NPC192768
0.8049	Intermediate Similarity	NPC220858
0.8049	Intermediate Similarity	NPC97221
0.8049	Intermediate Similarity	NPC88249
0.8049	Intermediate Similarity	NPC151895
0.8045	Intermediate Similarity	NPC237579
0.8037	Intermediate Similarity	NPC7467
0.8036	Intermediate Similarity	NPC69360
0.8035	Intermediate Similarity	NPC149090
0.8035	Intermediate Similarity	NPC19520
0.8023	Intermediate Similarity	NPC116284
0.8022	Intermediate Similarity	NPC33256
0.8012	Intermediate Similarity	NPC13916
0.8012	Intermediate Similarity	NPC264850
0.8	Intermediate Similarity	NPC124433
0.8	Intermediate Similarity	NPC241704
0.8	Intermediate Similarity	NPC293871
0.7988	Intermediate Similarity	NPC207824

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 NPC158148 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	170
0.1-0.2	596
0.2-0.3	924
0.3-0.4	2251
0.4-0.5	2732
0.5-0.6	1728
0.6-0.7	618
0.7-0.8	121
0.8-0.85	10
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8333	Intermediate Similarity	NPD6071	Discontinued
0.8303	Intermediate Similarity	NPD2560	Approved
0.8303	Intermediate Similarity	NPD2563	Approved
0.828	Intermediate Similarity	NPD4664	Clinical (unspecified phase)
0.8232	Intermediate Similarity	NPD4773	Phase 2
0.8232	Intermediate Similarity	NPD4772	Phase 2
0.8176	Intermediate Similarity	NPD2969	Approved
0.8176	Intermediate Similarity	NPD2970	Approved
0.8133	Intermediate Similarity	NPD6818	Clinical (unspecified phase)
0.8118	Intermediate Similarity	NPD3051	Approved
0.8113	Intermediate Similarity	NPD4236	Phase 3
0.8113	Intermediate Similarity	NPD4237	Approved
0.8086	Intermediate Similarity	NPD4584	Approved
0.8024	Intermediate Similarity	NPD2978	Approved
0.8024	Intermediate Similarity	NPD2977	Approved
0.8023	Intermediate Similarity	NPD2489	Approved
0.8023	Intermediate Similarity	NPD27	Approved
0.8012	Intermediate Similarity	NPD5241	Discontinued
0.7963	Intermediate Similarity	NPD6783	Clinical (unspecified phase)
0.7935	Intermediate Similarity	NPD4420	Approved
0.7923	Intermediate Similarity	NPD5582	Discontinued
0.7919	Intermediate Similarity	NPD4481	Phase 3
0.7901	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.7861	Intermediate Similarity	NPD5006	Approved
0.7861	Intermediate Similarity	NPD5005	Approved
0.7816	Intermediate Similarity	NPD2898	Approved
0.7811	Intermediate Similarity	NPD5772	Approved
0.7811	Intermediate Similarity	NPD5773	Approved
0.7791	Intermediate Similarity	NPD7201	Clinical (unspecified phase)
0.779	Intermediate Similarity	NPD7906	Approved
0.7765	Intermediate Similarity	NPD7280	Phase 3
0.7765	Intermediate Similarity	NPD7281	Phase 3
0.7746	Intermediate Similarity	NPD6107	Approved
0.7735	Intermediate Similarity	NPD4663	Approved
0.7725	Intermediate Similarity	NPD4210	Discontinued
0.7679	Intermediate Similarity	NPD4017	Approved
0.7667	Intermediate Similarity	NPD4578	Approved
0.7667	Intermediate Similarity	NPD7312	Approved
0.7667	Intermediate Similarity	NPD7310	Approved
0.7667	Intermediate Similarity	NPD7313	Approved
0.7667	Intermediate Similarity	NPD7311	Approved
0.7667	Intermediate Similarity	NPD4577	Approved
0.7665	Intermediate Similarity	NPD3639	Approved
0.7665	Intermediate Similarity	NPD3641	Approved
0.7665	Intermediate Similarity	NPD3640	Phase 3
0.7624	Intermediate Similarity	NPD7309	Approved
0.7596	Intermediate Similarity	NPD7243	Clinical (unspecified phase)
0.7584	Intermediate Similarity	NPD8156	Discontinued
0.7572	Intermediate Similarity	NPD7832	Clinical (unspecified phase)
0.7572	Intermediate Similarity	NPD7833	Phase 2
0.7572	Intermediate Similarity	NPD7831	Phase 2
0.7568	Intermediate Similarity	NPD7296	Approved
0.7561	Intermediate Similarity	NPD3060	Approved
0.756	Intermediate Similarity	NPD6031	Approved
0.756	Intermediate Similarity	NPD6030	Approved
0.7545	Intermediate Similarity	NPD1754	Clinical (unspecified phase)
0.7544	Intermediate Similarity	NPD7298	Approved
0.7532	Intermediate Similarity	NPD2669	Clinical (unspecified phase)
0.7528	Intermediate Similarity	NPD8099	Discontinued
0.7528	Intermediate Similarity	NPD8252	Approved
0.7528	Intermediate Similarity	NPD8251	Approved
0.7527	Intermediate Similarity	NPD8054	Approved
0.7527	Intermediate Similarity	NPD8053	Approved
0.75	Intermediate Similarity	NPD4010	Discontinued
0.75	Intermediate Similarity	NPD6297	Approved
0.7471	Intermediate Similarity	NPD5604	Discontinued
0.747	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7447	Intermediate Similarity	NPD7667	Clinical (unspecified phase)
0.7438	Intermediate Similarity	NPD554	Clinical (unspecified phase)
0.7432	Intermediate Similarity	NPD6851	Approved
0.7432	Intermediate Similarity	NPD6853	Approved
0.7414	Intermediate Similarity	NPD6788	Approved
0.7407	Intermediate Similarity	NPD2974	Approved
0.7407	Intermediate Similarity	NPD2975	Approved
0.7407	Intermediate Similarity	NPD2973	Approved
0.7401	Intermediate Similarity	NPD4166	Phase 2
0.7389	Intermediate Similarity	NPD5313	Approved
0.7389	Intermediate Similarity	NPD5312	Approved
0.7368	Intermediate Similarity	NPD4005	Discontinued
0.7349	Intermediate Similarity	NPD4162	Approved
0.7333	Intermediate Similarity	NPD1375	Discontinued
0.731	Intermediate Similarity	NPD3686	Approved
0.731	Intermediate Similarity	NPD3687	Approved
0.7292	Intermediate Similarity	NPD4580	Approved
0.7283	Intermediate Similarity	NPD2971	Approved
0.7283	Intermediate Similarity	NPD2968	Approved
0.7267	Intermediate Similarity	NPD5718	Phase 2
0.7263	Intermediate Similarity	NPD6687	Approved
0.7263	Intermediate Similarity	NPD6688	Approved
0.7256	Intermediate Similarity	NPD6895	Approved
0.7256	Intermediate Similarity	NPD6896	Approved
0.7254	Intermediate Similarity	NPD2494	Approved
0.7254	Intermediate Similarity	NPD3450	Approved
0.7254	Intermediate Similarity	NPD3452	Approved
0.7254	Intermediate Similarity	NPD2493	Approved
0.7251	Intermediate Similarity	NPD4727	Phase 1
0.7246	Intermediate Similarity	NPD5177	Phase 3
0.7243	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7235	Intermediate Similarity	NPD1424	Approved
0.7235	Intermediate Similarity	NPD4123	Phase 3
0.7234	Intermediate Similarity	NPD2488	Approved
0.7234	Intermediate Similarity	NPD2490	Approved
0.7234	Intermediate Similarity	NPD5525	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD6365	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD7124	Phase 2
0.7212	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7212	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7212	Intermediate Similarity	NPD1753	Discontinued
0.7195	Intermediate Similarity	NPD2492	Phase 1
0.7178	Intermediate Similarity	NPD2238	Phase 2
0.7176	Intermediate Similarity	NPD3124	Discontinued
0.7175	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7174	Intermediate Similarity	NPD7149	Clinical (unspecified phase)
0.7168	Intermediate Similarity	NPD7261	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD2677	Approved
0.7151	Intermediate Similarity	NPD5976	Discontinued
0.715	Intermediate Similarity	NPD7827	Phase 1
0.7143	Intermediate Similarity	NPD3808	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD4582	Approved
0.7143	Intermediate Similarity	NPD4583	Approved
0.7143	Intermediate Similarity	NPD7945	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD3705	Approved
0.7119	Intermediate Similarity	NPD4581	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD5677	Discontinued
0.7093	Intermediate Similarity	NPD7527	Clinical (unspecified phase)
0.7093	Intermediate Similarity	NPD7526	Approved
0.7093	Intermediate Similarity	NPD52	Approved
0.7092	Intermediate Similarity	NPD4002	Approved
0.7092	Intermediate Similarity	NPD4004	Approved
0.7091	Intermediate Similarity	NPD817	Approved
0.7091	Intermediate Similarity	NPD823	Approved
0.7088	Intermediate Similarity	NPD5602	Clinical (unspecified phase)
0.7087	Intermediate Similarity	NPD6997	Phase 2
0.7083	Intermediate Similarity	NPD1372	Clinical (unspecified phase)
0.7079	Intermediate Similarity	NPD4055	Discovery
0.7073	Intermediate Similarity	NPD3109	Approved
0.7073	Intermediate Similarity	NPD3110	Approved
0.7066	Intermediate Similarity	NPD2161	Phase 2
0.7065	Intermediate Similarity	NPD3885	Approved
0.7063	Intermediate Similarity	NPD4104	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD4103	Phase 2
0.7062	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD3692	Discontinued
0.7056	Intermediate Similarity	NPD7802	Discontinued
0.7051	Intermediate Similarity	NPD1357	Approved
0.7044	Intermediate Similarity	NPD7047	Phase 3
0.7041	Intermediate Similarity	NPD3057	Approved
0.7029	Intermediate Similarity	NPD4675	Approved
0.7029	Intermediate Similarity	NPD4678	Approved
0.702	Intermediate Similarity	NPD7607	Clinical (unspecified phase)
0.7012	Intermediate Similarity	NPD2674	Phase 3
0.7005	Intermediate Similarity	NPD3534	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD2041	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD7235	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD2042	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD2421	Approved
0.6977	Remote Similarity	NPD2420	Approved
0.6977	Remote Similarity	NPD1774	Approved
0.6966	Remote Similarity	NPD5977	Approved
0.6966	Remote Similarity	NPD5978	Approved
0.6959	Remote Similarity	NPD5160	Discontinued
0.6954	Remote Similarity	NPD2972	Approved
0.6954	Remote Similarity	NPD3533	Approved
0.6954	Remote Similarity	NPD2122	Discontinued
0.6952	Remote Similarity	NPD7132	Clinical (unspecified phase)
0.6949	Remote Similarity	NPD3383	Approved
0.6949	Remote Similarity	NPD3384	Approved
0.6949	Remote Similarity	NPD3382	Approved
0.6946	Remote Similarity	NPD6111	Discontinued
0.6944	Remote Similarity	NPD7400	Phase 3
0.6944	Remote Similarity	NPD5709	Phase 3
0.6939	Remote Similarity	NPD4107	Approved
0.6937	Remote Similarity	NPD4659	Approved
0.6936	Remote Similarity	NPD2874	Phase 2
0.6936	Remote Similarity	NPD7020	Approved
0.6936	Remote Similarity	NPD7019	Approved
0.6936	Remote Similarity	NPD4739	Approved
0.6935	Remote Similarity	NPD7007	Discovery
0.6931	Remote Similarity	NPD5676	Approved
0.6923	Remote Similarity	NPD3656	Approved
0.6919	Remote Similarity	NPD3845	Phase 1
0.6919	Remote Similarity	NPD3122	Phase 3
0.6909	Remote Similarity	NPD1130	Approved
0.6909	Remote Similarity	NPD4474	Approved
0.6909	Remote Similarity	NPD1136	Approved
0.6909	Remote Similarity	NPD1132	Approved
0.6909	Remote Similarity	NPD4475	Approved
0.6906	Remote Similarity	NPD2904	Discontinued
0.6906	Remote Similarity	NPD4666	Phase 3
0.6905	Remote Similarity	NPD4108	Discontinued
0.6901	Remote Similarity	NPD6658	Clinical (unspecified phase)
0.6901	Remote Similarity	NPD6331	Phase 2
0.6899	Remote Similarity	NPD2668	Approved
0.6899	Remote Similarity	NPD2667	Approved
0.6897	Remote Similarity	NPD6090	Discontinued
0.6895	Remote Similarity	NPD3857	Clinical (unspecified phase)
0.6893	Remote Similarity	NPD6072	Discontinued
0.689	Remote Similarity	NPD3179	Approved
0.689	Remote Similarity	NPD3180	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