NPASS Compound

Structure

NPC66573 OpenBabel07101719152D 34 38 0 0 1 0 0 0 0 0999 V2000 -4.3301 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 3.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.9282 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 2.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.0622 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 2.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.7942 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 3.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 3.0000 0.0000 N 0 0 3 0 0 0 0 0 0 0 0 0 -8.6603 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 5 1 0 0 0 0 2 32 1 0 0 0 0 3 33 1 0 0 0 0 4 34 1 0 0 0 0 6 8 1 0 0 0 0 6 18 1 0 0 0 0 7 9 1 0 0 0 0 7 19 1 0 0 0 0 8 29 1 0 0 0 0 9 30 1 0 0 0 0 10 23 1 0 0 0 0 11 20 1 0 0 0 0 11 24 1 0 0 0 0 12 18 2 0 0 0 0 12 25 1 0 0 0 0 13 19 2 0 0 0 0 13 27 1 0 0 0 0 14 21 2 0 0 0 0 14 26 1 0 0 0 0 15 22 2 0 0 0 0 15 28 1 0 0 0 0 16 17 1 0 0 0 0 16 30 1 0 0 0 0 17 5 1 1 0 0 0 17 20 1 0 0 0 0 18 21 1 0 0 0 0 19 22 1 0 0 0 0 20 10 1 6 0 0 0 21 23 1 0 0 0 0 22 24 1 0 0 0 0 23 29 2 0 0 0 0 24 30 1 6 0 0 0 25 26 2 0 0 0 0 25 31 1 0 0 0 0 26 32 1 0 0 0 0 27 28 2 0 0 0 0 27 33 1 0 0 0 0 28 34 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	464.27
Volume:	488.761
LogP:	4.715
LogD:	3.973
LogS:	-4.42
# Rotatable Bonds:	6
TPSA:	63.52
# H-Bond Aceptor:	6
# H-Bond Donor:	1
# Rings:	5
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.665
Synthetic Accessibility Score:	3.889
Fsp3:	0.536
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.553
MDCK Permeability:	1.751709532982204e-05
Pgp-inhibitor:	0.992
Pgp-substrate:	0.998
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.94
30% Bioavailability (F30%):	0.568

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.822
Plasma Protein Binding (PPB):	88.76229095458984%
Volume Distribution (VD):	1.693
Pgp-substrate:	4.863559722900391%

ADMET: Metabolism

CYP1A2-inhibitor:	0.091
CYP1A2-substrate:	0.947
CYP2C19-inhibitor:	0.061
CYP2C19-substrate:	0.929
CYP2C9-inhibitor:	0.035
CYP2C9-substrate:	0.435
CYP2D6-inhibitor:	0.737
CYP2D6-substrate:	0.932
CYP3A4-inhibitor:	0.111
CYP3A4-substrate:	0.928

ADMET: Excretion

Clearance (CL):	10.815
Half-life (T1/2):	0.587

ADMET: Toxicity

hERG Blockers:	0.939
Human Hepatotoxicity (H-HT):	0.254
Drug-inuced Liver Injury (DILI):	0.905
AMES Toxicity:	0.029
Rat Oral Acute Toxicity:	0.409
Maximum Recommended Daily Dose:	0.971
Skin Sensitization:	0.82
Carcinogencity:	0.032
Eye Corrosion:	0.003
Eye Irritation:	0.011
Respiratory Toxicity:	0.837

Download Data

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

Natural Product: NPC66573

Natural Product ID:	NPC66573
*Common Name:**	Psychotrine
IUPAC Name:	n.a.
Synonyms:	Psychotrine
Standard InCHIKey:	NCALAYAMQHIWMN-REIDKSKDSA-N
Standard InCHI:	InChI=1S/C28H36N2O4/c1-5-17-16-30-9-7-19-13-27(33-3)28(34-4)15-22(19)24(30)11-20(17)10-23-21-14-26(32-2)25(31)12-18(21)6-8-29-23/h12-15,17,20,24,31H,5-11,16H2,1-4H3/t17-,20-,24-/m0/s1
SMILES:	CC[C@H]1CN2CCc3c([C@@H]2C[C@@H]1CC1=NCCc2c1cc(OC)c(c2)O)cc(c(c3)OC)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL463445
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids and derivatives [CHEMONTID:0002659] Emetine 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
NPO28941	Pogonopus speciosus	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10514334]
NPO28941	Pogonopus speciosus	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[1982768]
NPO28941	Pogonopus speciosus	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	2

Activity Type	# Activity
Cell Line	12
Individual Protein	2
NON-MOLECULAR	2
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	ED50	>	10.0	ug ml-1	PMID[485179]
NPT83	Cell Line	MCF7	Homo sapiens	ED50	>	10.0	ug ml-1	PMID[485179]
NPT139	Cell Line	HT-29	Homo sapiens	ED50	>	10.0	ug ml-1	PMID[485179]
NPT459	Individual Protein	Human immunodeficiency virus type 1 reverse transcriptase	Human immunodeficiency virus 1	IC50	>	200.0	ug.mL-1	PMID[485180]
NPT459	Individual Protein	Human immunodeficiency virus type 1 reverse transcriptase	Human immunodeficiency virus 1	Inhibition	=	20.0	%	PMID[485180]
NPT1034	Cell Line	Lu1	Homo sapiens	ED50	=	5.7	ug ml-1	PMID[485181]
NPT1851	Cell Line	Col2	Homo sapiens	ED50	=	4.5	ug ml-1	PMID[485181]
NPT91	Cell Line	KB	Homo sapiens	ED50	=	2.8	ug ml-1	PMID[485181]
NPT91	Cell Line	KB	Homo sapiens	ED50	=	9.0	ug ml-1	PMID[485181]
NPT91	Cell Line	KB	Homo sapiens	ED50	=	9.4	ug ml-1	PMID[485181]
NPT858	Cell Line	LNCaP	Homo sapiens	ED50	=	2.3	ug ml-1	PMID[485181]
NPT2345	Cell Line	SW626	Homo sapiens	ED50	=	13.3	ug ml-1	PMID[485181]
NPT136	Cell Line	SK-N-SH	Homo sapiens	ED50	=	4.0	ug ml-1	PMID[485181]
NPT726	Cell Line	M109	Mus musculus	ED50	=	9.0	ug ml-1	PMID[485181]
NPT140	Organism	Artemia	Artemia	LC50	>	1000.0	ppm	PMID[485179]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	ED50	=	1.0	ug ml-1	PMID[485179]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	ED50	=	3.4	ug ml-1	PMID[485181]
NPT992	Organism	Entamoeba histolytica	Entamoeba histolytica	IC50	=	8.19	ug.mL-1	PMID[485182]

☑ 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 NPC66573 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	287
0.1-0.2	1442
0.2-0.3	6895
0.3-0.4	10685
0.4-0.5	7065
0.5-0.6	12273
0.6-0.7	3201
0.7-0.8	655
0.8-0.85	139
0.85-0.9	50
0.9-0.95	3
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9548	High Similarity	NPC216816
0.9097	High Similarity	NPC192768
0.9097	High Similarity	NPC220858
0.9097	High Similarity	NPC97221
0.9097	High Similarity	NPC88249
0.9097	High Similarity	NPC151895
0.8951	High Similarity	NPC121275
0.8951	High Similarity	NPC4138
0.8951	High Similarity	NPC284183
0.8917	High Similarity	NPC476568
0.8868	High Similarity	NPC39701
0.8868	High Similarity	NPC54379
0.8868	High Similarity	NPC249797
0.8868	High Similarity	NPC127674
0.8868	High Similarity	NPC278799
0.8868	High Similarity	NPC110416
0.8868	High Similarity	NPC207757
0.8868	High Similarity	NPC5238
0.8868	High Similarity	NPC184026
0.8868	High Similarity	NPC204828
0.8868	High Similarity	NPC469817
0.8868	High Similarity	NPC276588
0.8868	High Similarity	NPC172765
0.8868	High Similarity	NPC189266
0.8868	High Similarity	NPC295691
0.8868	High Similarity	NPC193949
0.8868	High Similarity	NPC2413
0.8846	High Similarity	NPC24233
0.8846	High Similarity	NPC476571
0.8846	High Similarity	NPC147390
0.8846	High Similarity	NPC246587
0.8846	High Similarity	NPC135538
0.8846	High Similarity	NPC428
0.8782	High Similarity	NPC321505
0.8782	High Similarity	NPC191376
0.8782	High Similarity	NPC179825
0.878	High Similarity	NPC256012
0.878	High Similarity	NPC42549
0.878	High Similarity	NPC240841
0.878	High Similarity	NPC317272
0.878	High Similarity	NPC268503
0.878	High Similarity	NPC250846
0.8735	High Similarity	NPC109925
0.8704	High Similarity	NPC111485
0.8686	High Similarity	NPC85381
0.8678	High Similarity	NPC41122
0.8678	High Similarity	NPC318805
0.8654	High Similarity	NPC185838
0.8645	High Similarity	NPC476567
0.8645	High Similarity	NPC136860
0.8645	High Similarity	NPC128019
0.8553	High Similarity	NPC103379
0.8553	High Similarity	NPC477565
0.8519	High Similarity	NPC187022
0.8519	High Similarity	NPC80129
0.8509	High Similarity	NPC37272
0.8494	Intermediate Similarity	NPC276944
0.8494	Intermediate Similarity	NPC238530
0.8494	Intermediate Similarity	NPC24465
0.8494	Intermediate Similarity	NPC232514
0.8491	Intermediate Similarity	NPC7467
0.8483	Intermediate Similarity	NPC234318
0.8462	Intermediate Similarity	NPC475215
0.8462	Intermediate Similarity	NPC108434
0.8447	Intermediate Similarity	NPC76213
0.8447	Intermediate Similarity	NPC277669
0.8443	Intermediate Similarity	NPC264850
0.8443	Intermediate Similarity	NPC13916
0.8428	Intermediate Similarity	NPC476144
0.8428	Intermediate Similarity	NPC106295
0.8428	Intermediate Similarity	NPC210437
0.8428	Intermediate Similarity	NPC16107
0.8428	Intermediate Similarity	NPC51957
0.8428	Intermediate Similarity	NPC476151
0.8397	Intermediate Similarity	NPC213206
0.8397	Intermediate Similarity	NPC328750
0.8397	Intermediate Similarity	NPC188163
0.8397	Intermediate Similarity	NPC474915
0.8354	Intermediate Similarity	NPC247639
0.8354	Intermediate Similarity	NPC25084
0.8343	Intermediate Similarity	NPC249996
0.8333	Intermediate Similarity	NPC314682
0.8333	Intermediate Similarity	NPC476202
0.8323	Intermediate Similarity	NPC324144
0.8323	Intermediate Similarity	NPC207824
0.8323	Intermediate Similarity	NPC60538
0.8313	Intermediate Similarity	NPC27410
0.8313	Intermediate Similarity	NPC166014
0.8276	Intermediate Similarity	NPC195538
0.8276	Intermediate Similarity	NPC286119
0.8274	Intermediate Similarity	NPC253043
0.8274	Intermediate Similarity	NPC196447
0.8274	Intermediate Similarity	NPC306843
0.8274	Intermediate Similarity	NPC96603
0.8274	Intermediate Similarity	NPC212794
0.8274	Intermediate Similarity	NPC477563
0.8274	Intermediate Similarity	NPC78222
0.8274	Intermediate Similarity	NPC136508
0.8274	Intermediate Similarity	NPC13504
0.8258	Intermediate Similarity	NPC131204
0.8258	Intermediate Similarity	NPC301050
0.8242	Intermediate Similarity	NPC186063
0.8232	Intermediate Similarity	NPC477564
0.8232	Intermediate Similarity	NPC2295
0.8229	Intermediate Similarity	NPC42663
0.8229	Intermediate Similarity	NPC271013
0.8229	Intermediate Similarity	NPC258657
0.8229	Intermediate Similarity	NPC217748
0.8229	Intermediate Similarity	NPC49075
0.8229	Intermediate Similarity	NPC279228
0.8229	Intermediate Similarity	NPC8836
0.8229	Intermediate Similarity	NPC90998
0.8229	Intermediate Similarity	NPC7715
0.8229	Intermediate Similarity	NPC328155
0.8229	Intermediate Similarity	NPC15414
0.8229	Intermediate Similarity	NPC251735
0.8229	Intermediate Similarity	NPC182052
0.8229	Intermediate Similarity	NPC229373
0.8229	Intermediate Similarity	NPC239824
0.8229	Intermediate Similarity	NPC290582
0.8229	Intermediate Similarity	NPC104196
0.8229	Intermediate Similarity	NPC185639
0.8229	Intermediate Similarity	NPC290005
0.8229	Intermediate Similarity	NPC181796
0.8229	Intermediate Similarity	NPC223690
0.8229	Intermediate Similarity	NPC54654
0.8229	Intermediate Similarity	NPC285931
0.8229	Intermediate Similarity	NPC222661
0.8229	Intermediate Similarity	NPC311973
0.8229	Intermediate Similarity	NPC30779
0.8204	Intermediate Similarity	NPC205167
0.8182	Intermediate Similarity	NPC167116
0.8182	Intermediate Similarity	NPC274716
0.8182	Intermediate Similarity	NPC254441
0.8176	Intermediate Similarity	NPC12053
0.8176	Intermediate Similarity	NPC117188
0.8176	Intermediate Similarity	NPC205421
0.8176	Intermediate Similarity	NPC306555
0.8176	Intermediate Similarity	NPC145832
0.8176	Intermediate Similarity	NPC81218
0.8176	Intermediate Similarity	NPC158376
0.8176	Intermediate Similarity	NPC474931
0.8171	Intermediate Similarity	NPC233029
0.8171	Intermediate Similarity	NPC133011
0.8171	Intermediate Similarity	NPC82285
0.8171	Intermediate Similarity	NPC210148
0.8133	Intermediate Similarity	NPC146288
0.8133	Intermediate Similarity	NPC147091
0.8125	Intermediate Similarity	NPC294249
0.8107	Intermediate Similarity	NPC475393
0.8098	Intermediate Similarity	NPC92541
0.8095	Intermediate Similarity	NPC249274
0.809	Intermediate Similarity	NPC212237
0.809	Intermediate Similarity	NPC116465
0.8072	Intermediate Similarity	NPC41178
0.8072	Intermediate Similarity	NPC138487
0.8072	Intermediate Similarity	NPC216459
0.807	Intermediate Similarity	NPC210140
0.8047	Intermediate Similarity	NPC60186
0.8045	Intermediate Similarity	NPC275680
0.8045	Intermediate Similarity	NPC22115
0.8037	Intermediate Similarity	NPC475959
0.8035	Intermediate Similarity	NPC239775
0.8023	Intermediate Similarity	NPC83198
0.8023	Intermediate Similarity	NPC204908
0.8013	Intermediate Similarity	NPC218530
0.8012	Intermediate Similarity	NPC81247
0.8012	Intermediate Similarity	NPC35627
0.8012	Intermediate Similarity	NPC476573
0.8011	Intermediate Similarity	NPC32154
0.8	Intermediate Similarity	NPC274661
0.8	Intermediate Similarity	NPC48490
0.8	Intermediate Similarity	NPC206900
0.8	Intermediate Similarity	NPC175890
0.8	Intermediate Similarity	NPC1229
0.8	Intermediate Similarity	NPC82457
0.8	Intermediate Similarity	NPC11296
0.7977	Intermediate Similarity	NPC69712
0.7977	Intermediate Similarity	NPC477562
0.7977	Intermediate Similarity	NPC26240
0.7975	Intermediate Similarity	NPC144863
0.7963	Intermediate Similarity	NPC5462
0.7956	Intermediate Similarity	NPC191132
0.7956	Intermediate Similarity	NPC60295
0.7953	Intermediate Similarity	NPC134858
0.7953	Intermediate Similarity	NPC169743
0.7952	Intermediate Similarity	NPC275027
0.7952	Intermediate Similarity	NPC18614
0.7952	Intermediate Similarity	NPC26601
0.7949	Intermediate Similarity	NPC6854
0.7949	Intermediate Similarity	NPC285078
0.7949	Intermediate Similarity	NPC313737
0.7943	Intermediate Similarity	NPC199465
0.7943	Intermediate Similarity	NPC229166
0.7943	Intermediate Similarity	NPC128560
0.7939	Intermediate Similarity	NPC274026
0.7933	Intermediate Similarity	NPC302245
0.7933	Intermediate Similarity	NPC95426
0.7933	Intermediate Similarity	NPC16357
0.7917	Intermediate Similarity	NPC31311

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 NPC66573 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	176
0.1-0.2	609
0.2-0.3	936
0.3-0.4	1593
0.4-0.5	2836
0.5-0.6	2080
0.6-0.7	754
0.7-0.8	154
0.8-0.85	10
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8519	High Similarity	NPD7298	Approved
0.8512	High Similarity	NPD5602	Clinical (unspecified phase)
0.8434	Intermediate Similarity	NPD7201	Clinical (unspecified phase)
0.8428	Intermediate Similarity	NPD4584	Approved
0.8397	Intermediate Similarity	NPD4664	Clinical (unspecified phase)
0.8232	Intermediate Similarity	NPD4773	Phase 2
0.8232	Intermediate Similarity	NPD4772	Phase 2
0.8229	Intermediate Similarity	NPD8054	Approved
0.8229	Intermediate Similarity	NPD8053	Approved
0.8118	Intermediate Similarity	NPD4010	Discontinued
0.7988	Intermediate Similarity	NPD3639	Approved
0.7988	Intermediate Similarity	NPD3641	Approved
0.7988	Intermediate Similarity	NPD3640	Phase 3
0.795	Intermediate Similarity	NPD6658	Clinical (unspecified phase)
0.7892	Intermediate Similarity	NPD4005	Discontinued
0.7889	Intermediate Similarity	NPD7291	Discontinued
0.7885	Intermediate Similarity	NPD2674	Phase 3
0.7829	Intermediate Similarity	NPD8251	Approved
0.7829	Intermediate Similarity	NPD8252	Approved
0.7829	Intermediate Similarity	NPD8099	Discontinued
0.7821	Intermediate Similarity	NPD3144	Approved
0.7821	Intermediate Similarity	NPD3145	Approved
0.7811	Intermediate Similarity	NPD6818	Clinical (unspecified phase)
0.7809	Intermediate Similarity	NPD7132	Clinical (unspecified phase)
0.7784	Intermediate Similarity	NPD8156	Discontinued
0.7784	Intermediate Similarity	NPD4017	Approved
0.7778	Intermediate Similarity	NPD7832	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD7831	Phase 2
0.7778	Intermediate Similarity	NPD7833	Phase 2
0.7758	Intermediate Similarity	NPD1754	Clinical (unspecified phase)
0.7746	Intermediate Similarity	NPD6107	Approved
0.7714	Intermediate Similarity	NPD2898	Approved
0.7683	Intermediate Similarity	NPD5241	Discontinued
0.7665	Intermediate Similarity	NPD2122	Discontinued
0.7614	Intermediate Similarity	NPD2489	Approved
0.7614	Intermediate Similarity	NPD27	Approved
0.7595	Intermediate Similarity	NPD5718	Phase 2
0.7594	Intermediate Similarity	NPD7034	Discontinued
0.759	Intermediate Similarity	NPD3124	Discontinued
0.759	Intermediate Similarity	NPD2420	Approved
0.759	Intermediate Similarity	NPD2421	Approved
0.7569	Intermediate Similarity	NPD5917	Clinical (unspecified phase)
0.756	Intermediate Similarity	NPD6030	Approved
0.756	Intermediate Similarity	NPD6031	Approved
0.7545	Intermediate Similarity	NPD4123	Phase 3
0.7531	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7531	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.753	Intermediate Similarity	NPD2422	Clinical (unspecified phase)
0.753	Intermediate Similarity	NPD3845	Phase 1
0.7515	Intermediate Similarity	NPD6331	Phase 2
0.75	Intermediate Similarity	NPD4166	Phase 2
0.7486	Intermediate Similarity	NPD5313	Approved
0.7486	Intermediate Similarity	NPD5312	Approved
0.7473	Intermediate Similarity	NPD7310	Approved
0.7473	Intermediate Similarity	NPD7312	Approved
0.7473	Intermediate Similarity	NPD7313	Approved
0.7473	Intermediate Similarity	NPD7311	Approved
0.7471	Intermediate Similarity	NPD5604	Discontinued
0.747	Intermediate Similarity	NPD3692	Discontinued
0.7469	Intermediate Similarity	NPD6896	Approved
0.7469	Intermediate Similarity	NPD6895	Approved
0.7458	Intermediate Similarity	NPD2970	Approved
0.7458	Intermediate Similarity	NPD2969	Approved
0.7458	Intermediate Similarity	NPD4083	Discontinued
0.7443	Intermediate Similarity	NPD7802	Discontinued
0.7442	Intermediate Similarity	NPD7945	Clinical (unspecified phase)
0.7432	Intermediate Similarity	NPD7309	Approved
0.7421	Intermediate Similarity	NPD2669	Clinical (unspecified phase)
0.7403	Intermediate Similarity	NPD6297	Approved
0.7401	Intermediate Similarity	NPD3051	Approved
0.7401	Intermediate Similarity	NPD6071	Discontinued
0.7399	Intermediate Similarity	NPD5773	Approved
0.7399	Intermediate Similarity	NPD5772	Approved
0.7378	Intermediate Similarity	NPD1632	Clinical (unspecified phase)
0.7375	Intermediate Similarity	NPD5109	Approved
0.7375	Intermediate Similarity	NPD5111	Phase 2
0.7375	Intermediate Similarity	NPD5110	Phase 2
0.7348	Intermediate Similarity	NPD3920	Phase 2
0.7337	Intermediate Similarity	NPD6853	Approved
0.7337	Intermediate Similarity	NPD6851	Approved
0.7326	Intermediate Similarity	NPD4675	Approved
0.7326	Intermediate Similarity	NPD4678	Approved
0.7322	Intermediate Similarity	NPD8453	Clinical (unspecified phase)
0.7314	Intermediate Similarity	NPD6788	Approved
0.7312	Intermediate Similarity	NPD7906	Approved
0.7308	Intermediate Similarity	NPD6996	Clinical (unspecified phase)
0.7292	Intermediate Similarity	NPD6612	Phase 2
0.7289	Intermediate Similarity	NPD7153	Discontinued
0.7287	Intermediate Similarity	NPD3924	Approved
0.7287	Intermediate Similarity	NPD3923	Approved
0.7287	Intermediate Similarity	NPD3921	Approved
0.7287	Intermediate Similarity	NPD3922	Approved
0.7283	Intermediate Similarity	NPD3534	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD4055	Discovery
0.7267	Intermediate Similarity	NPD7261	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7246	Intermediate Similarity	NPD5177	Phase 3
0.7193	Intermediate Similarity	NPD52	Approved
0.7193	Intermediate Similarity	NPD7526	Approved
0.7193	Intermediate Similarity	NPD7527	Clinical (unspecified phase)
0.7189	Intermediate Similarity	NPD4578	Approved
0.7189	Intermediate Similarity	NPD4577	Approved
0.7184	Intermediate Similarity	NPD7109	Clinical (unspecified phase)
0.7184	Intermediate Similarity	NPD7110	Phase 1
0.7181	Intermediate Similarity	NPD6377	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD7598	Phase 2
0.7173	Intermediate Similarity	NPD7667	Clinical (unspecified phase)
0.7169	Intermediate Similarity	NPD2161	Phase 2
0.7166	Intermediate Similarity	NPD4663	Approved
0.7159	Intermediate Similarity	NPD2560	Approved
0.7159	Intermediate Similarity	NPD2563	Approved
0.7151	Intermediate Similarity	NPD6618	Phase 2
0.7143	Intermediate Similarity	NPD7493	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD5525	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD3060	Approved
0.7126	Intermediate Similarity	NPD3656	Approved
0.7118	Intermediate Similarity	NPD7124	Phase 2
0.7102	Intermediate Similarity	NPD2978	Approved
0.7102	Intermediate Similarity	NPD2977	Approved
0.7097	Intermediate Similarity	NPD7281	Phase 3
0.7097	Intermediate Similarity	NPD7280	Phase 3
0.7093	Intermediate Similarity	NPD6090	Discontinued
0.7088	Intermediate Similarity	NPD5966	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD7438	Suspended
0.7083	Intermediate Similarity	NPD7045	Clinical (unspecified phase)
0.7079	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD3109	Approved
0.7073	Intermediate Similarity	NPD3110	Approved
0.7072	Intermediate Similarity	NPD6687	Approved
0.7072	Intermediate Similarity	NPD6688	Approved
0.7069	Intermediate Similarity	NPD6523	Clinical (unspecified phase)
0.7062	Intermediate Similarity	NPD5978	Approved
0.7062	Intermediate Similarity	NPD8095	Phase 1
0.7062	Intermediate Similarity	NPD3837	Clinical (unspecified phase)
0.7062	Intermediate Similarity	NPD5977	Approved
0.7059	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.7053	Intermediate Similarity	NPD2488	Approved
0.7053	Intermediate Similarity	NPD2490	Approved
0.7053	Intermediate Similarity	NPD6656	Clinical (unspecified phase)
0.7044	Intermediate Similarity	NPD1669	Approved
0.7041	Intermediate Similarity	NPD44	Approved
0.7041	Intermediate Similarity	NPD6364	Approved
0.7033	Intermediate Similarity	NPD4481	Phase 3
0.7029	Intermediate Similarity	NPD6876	Approved
0.7029	Intermediate Similarity	NPD6875	Approved
0.7018	Intermediate Similarity	NPD6783	Clinical (unspecified phase)
0.7011	Intermediate Similarity	NPD5267	Discontinued
0.7011	Intermediate Similarity	NPD2883	Discontinued
0.7006	Intermediate Similarity	NPD1753	Discontinued
0.7	Intermediate Similarity	NPD3408	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD5261	Clinical (unspecified phase)
0.698	Remote Similarity	NPD3815	Phase 1
0.698	Remote Similarity	NPD3816	Phase 1
0.6979	Remote Similarity	NPD6046	Clinical (unspecified phase)
0.6973	Remote Similarity	NPD7479	Phase 2
0.6966	Remote Similarity	NPD6063	Approved
0.6961	Remote Similarity	NPD8149	Discontinued
0.6959	Remote Similarity	NPD5307	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD3053	Approved
0.6957	Remote Similarity	NPD3055	Approved
0.6954	Remote Similarity	NPD6662	Clinical (unspecified phase)
0.6951	Remote Similarity	NPD2028	Clinical (unspecified phase)
0.6949	Remote Similarity	NPD5720	Discontinued
0.6947	Remote Similarity	NPD7243	Clinical (unspecified phase)
0.6941	Remote Similarity	NPD2460	Phase 3
0.6941	Remote Similarity	NPD2458	Approved
0.6941	Remote Similarity	NPD2459	Approved
0.6941	Remote Similarity	NPD4162	Approved
0.694	Remote Similarity	NPD6607	Clinical (unspecified phase)
0.6937	Remote Similarity	NPD3676	Clinical (unspecified phase)
0.6936	Remote Similarity	NPD2874	Phase 2
0.6927	Remote Similarity	NPD4581	Clinical (unspecified phase)
0.691	Remote Similarity	NPD6060	Clinical (unspecified phase)
0.6909	Remote Similarity	NPD7477	Discontinued
0.6905	Remote Similarity	NPD4108	Discontinued
0.6905	Remote Similarity	NPD6380	Phase 1
0.6899	Remote Similarity	NPD2668	Approved
0.6899	Remote Similarity	NPD2667	Approved
0.6897	Remote Similarity	NPD7827	Phase 1
0.6894	Remote Similarity	NPD5311	Approved
0.6894	Remote Similarity	NPD7258	Clinical (unspecified phase)
0.6894	Remote Similarity	NPD5310	Approved
0.6894	Remote Similarity	NPD2922	Phase 1
0.6893	Remote Similarity	NPD6072	Discontinued
0.689	Remote Similarity	NPD5155	Approved
0.689	Remote Similarity	NPD5156	Approved
0.6889	Remote Similarity	NPD8070	Approved
0.6878	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD2232	Approved
0.6875	Remote Similarity	NPD2230	Approved
0.6875	Remote Similarity	NPD5641	Discontinued
0.6875	Remote Similarity	NPD824	Approved
0.6875	Remote Similarity	NPD2233	Approved
0.6875	Remote Similarity	NPD2337	Clinical (unspecified phase)
0.6871	Remote Similarity	NPD3636	Approved
0.6871	Remote Similarity	NPD3635	Approved
0.6871	Remote Similarity	NPD3637	Approved
0.6867	Remote Similarity	NPD6346	Approved
0.686	Remote Similarity	NPD8318	Clinical (unspecified phase)
0.6859	Remote Similarity	NPD3349	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