NPASS Compound

Structure

CID75958 OpenBabel06191715412D 23 27 0 0 1 0 0 0 0 0999 V2000 5.3735 -3.7432 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3326 1.4452 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8757 -2.9046 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1155 -2.4658 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9933 -1.5879 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3146 -1.0314 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6359 -1.5879 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5951 -1.5880 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1155 0.1677 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5160 -0.7102 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6359 -2.4657 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.3553 -0.2713 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3553 -1.1491 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8349 -1.1491 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8757 -1.1490 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.5951 0.1676 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8349 -0.2713 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1155 -1.5879 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.8757 -0.2712 0.0000 N 0 0 3 0 0 0 0 0 0 0 0 0 5.3735 -2.8915 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5951 1.0193 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.4203 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 20 1 0 0 0 0 2 21 1 0 0 0 0 3 4 2 0 0 0 0 3 11 1 0 0 0 0 5 6 1 0 0 0 0 5 18 1 0 0 0 0 6 19 1 0 0 0 0 7 11 1 0 0 0 0 7 15 1 0 0 0 0 8 13 2 0 0 0 0 8 14 1 0 0 0 0 9 12 1 0 0 0 0 9 19 1 0 0 0 0 10 22 1 0 0 0 0 10 23 1 0 0 0 0 11 20 1 1 0 0 0 12 13 1 0 0 0 0 12 16 2 0 0 0 0 13 18 1 0 0 0 0 14 17 2 0 0 0 0 14 22 1 0 0 0 0 15 18 1 6 0 0 0 15 19 1 0 0 0 0 16 17 1 0 0 0 0 16 21 1 0 0 0 0 17 23 1 0 0 0 0 18 4 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	315.15
Volume:	312.714
LogP:	1.88
LogD:	1.561
LogS:	-2.259
# Rotatable Bonds:	2
TPSA:	40.16
# H-Bond Aceptor:	5
# H-Bond Donor:	0
# Rings:	5
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.783
Synthetic Accessibility Score:	4.99
Fsp3:	0.556
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:	-4.68
MDCK Permeability:	2.5465515136602335e-05
Pgp-inhibitor:	0.008
Pgp-substrate:	0.287
Human Intestinal Absorption (HIA):	0.002
20% Bioavailability (F20%):	0.071
30% Bioavailability (F30%):	0.238

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.996
Plasma Protein Binding (PPB):	40.36838912963867%
Volume Distribution (VD):	2.142
Pgp-substrate:	35.88642120361328%

ADMET: Metabolism

CYP1A2-inhibitor:	0.461
CYP1A2-substrate:	0.926
CYP2C19-inhibitor:	0.245
CYP2C19-substrate:	0.867
CYP2C9-inhibitor:	0.061
CYP2C9-substrate:	0.53
CYP2D6-inhibitor:	0.865
CYP2D6-substrate:	0.699
CYP3A4-inhibitor:	0.915
CYP3A4-substrate:	0.856

ADMET: Excretion

Clearance (CL):	11.318
Half-life (T1/2):	0.487

ADMET: Toxicity

hERG Blockers:	0.217
Human Hepatotoxicity (H-HT):	0.57
Drug-inuced Liver Injury (DILI):	0.093
AMES Toxicity:	0.171
Rat Oral Acute Toxicity:	0.654
Maximum Recommended Daily Dose:	0.906
Skin Sensitization:	0.07
Carcinogencity:	0.649
Eye Corrosion:	0.003
Eye Irritation:	0.01
Respiratory Toxicity:	0.893

Download Data

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

Natural Product: NPC75958

Natural Product ID:	NPC75958
*Common Name:**	Buphanidrine
IUPAC Name:	n.a.
Synonyms:	Buphanidrine
Standard InCHIKey:	RNEXSBPDDRJJIY-BKGUAONASA-N
Standard InCHI:	InChI=1S/C18H21NO4/c1-20-11-3-4-18-5-6-19(15(18)7-11)9-12-13(18)8-14-17(16(12)21-2)23-10-22-14/h3-4,8,11,15H,5-7,9-10H2,1-2H3/t11-,15+,18+/m0/s1
SMILES:	CO[C@H]1C=C[C@@]23[C@@H](C1)N(CC2)Cc1c3cc2OCOc2c1OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2146603
PubChem CID:	338023
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
NPO13176	Garcinia densivenia	Species	Clusiaceae	Eukaryota	n.a.	stem	n.a.	DOI[10.1016/S0031-9422(00)83950-3]
NPO11841	Psorothamnus arborescens	Species	Fabaceae	Eukaryota	n.a.	root	n.a.	PMID[16441066]
NPO11841	Psorothamnus arborescens	Species	Fabaceae	Eukaryota	root	n.a.	n.a.	PMID[16441066]
NPO33437	amaryllidaceae	Family	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22921081]
NPO4617	Tanacetum cinerariifolium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24253739]
NPO11658	Alternanthera philoxeroides	Species	Amaranthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11658	Alternanthera philoxeroides	Species	Amaranthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4617	Tanacetum cinerariifolium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25221	Crinum macowanii	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12363	Dermocybe sanguinea	Species	Cortinariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10281	Fritillaria roylei	Species	Liliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11658	Alternanthera philoxeroides	Species	Amaranthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13176	Garcinia densivenia	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4617	Tanacetum cinerariifolium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2381	Phacelocarpus peperocarpos	Species	Phacelocarpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4020	Dorstenia turbinata	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27248	Artemisia pygmaea	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13772	Didemnum proliferum	Species	Didemnidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25221	Crinum macowanii	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5924	Brunsvigia josephinae	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13027	Eucalyptus torelliana	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11841	Psorothamnus arborescens	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11265	Coryphantha cornifera	Species	Cactaceae	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
IC50	6
MIC	4

Activity Type	# Activity
Cell Line	6
Organism	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1160	Cell Line	BJ	Homo sapiens	IC50	=	26200.0	nM	PMID[476519]
NPT2468	Cell Line	G-361	Homo sapiens	IC50	>	50000.0	nM	PMID[476519]
NPT165	Cell Line	HeLa	Homo sapiens	IC50	>	50000.0	nM	PMID[476519]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	>	50000.0	nM	PMID[476519]
NPT111	Cell Line	K562	Homo sapiens	IC50	>	50000.0	nM	PMID[476519]
NPT404	Cell Line	CCRF-CEM	Homo sapiens	IC50	>	50000.0	nM	PMID[476519]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	=	130.0	ug.mL-1	PMID[476520]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	=	63.0	ug.mL-1	PMID[476520]
NPT173	Organism	Klebsiella pneumoniae	Klebsiella pneumoniae	MIC	=	63.0	ug.mL-1	PMID[476520]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	63.0	ug.mL-1	PMID[476520]

☑ 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 NPC75958 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	345
0.1-0.2	1481
0.2-0.3	5406
0.3-0.4	12326
0.4-0.5	6406
0.5-0.6	12326
0.6-0.7	3374
0.7-0.8	800
0.8-0.85	153
0.85-0.9	66
0.9-0.95	12
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.963	High Similarity	NPC244554
0.9295	High Similarity	NPC78733
0.9202	High Similarity	NPC65403
0.9198	High Similarity	NPC82533
0.9198	High Similarity	NPC290759
0.9198	High Similarity	NPC158148
0.9198	High Similarity	NPC266176
0.9085	High Similarity	NPC470739
0.9085	High Similarity	NPC225597
0.9085	High Similarity	NPC477640
0.908	High Similarity	NPC475686
0.908	High Similarity	NPC58766
0.9053	High Similarity	NPC9867
0.9024	High Similarity	NPC474475
0.9012	High Similarity	NPC180306
0.9012	High Similarity	NPC247972
0.8944	High Similarity	NPC215829
0.8944	High Similarity	NPC97072
0.8922	High Similarity	NPC474470
0.891	High Similarity	NPC59907
0.891	High Similarity	NPC37144
0.8909	High Similarity	NPC311991
0.8902	High Similarity	NPC474324
0.8902	High Similarity	NPC100566
0.8902	High Similarity	NPC57812
0.8869	High Similarity	NPC15919
0.8848	High Similarity	NPC475845
0.8844	High Similarity	NPC63152
0.8834	High Similarity	NPC320104
0.8805	High Similarity	NPC148898
0.8795	High Similarity	NPC474708
0.8788	High Similarity	NPC181653
0.8788	High Similarity	NPC190332
0.8758	High Similarity	NPC234392
0.8758	High Similarity	NPC31311
0.8743	High Similarity	NPC149090
0.8743	High Similarity	NPC19520
0.872	High Similarity	NPC218614
0.8696	High Similarity	NPC41178
0.8696	High Similarity	NPC216459
0.8696	High Similarity	NPC138487
0.8671	High Similarity	NPC475959
0.8647	High Similarity	NPC148693
0.8647	High Similarity	NPC294790
0.8647	High Similarity	NPC118633
0.8642	High Similarity	NPC146288
0.8639	High Similarity	NPC187678
0.8639	High Similarity	NPC304675
0.8605	High Similarity	NPC73492
0.8605	High Similarity	NPC299990
0.8588	High Similarity	NPC237044
0.858	High Similarity	NPC2314
0.8571	High Similarity	NPC210148
0.8571	High Similarity	NPC233029
0.8563	High Similarity	NPC210918
0.8563	High Similarity	NPC252960
0.8538	High Similarity	NPC474325
0.8503	High Similarity	NPC24264
0.8503	High Similarity	NPC476002
0.8503	High Similarity	NPC476432
0.8488	Intermediate Similarity	NPC474745
0.8457	Intermediate Similarity	NPC214116
0.8452	Intermediate Similarity	NPC247389
0.8448	Intermediate Similarity	NPC475981
0.8448	Intermediate Similarity	NPC474746
0.8447	Intermediate Similarity	NPC223125
0.8443	Intermediate Similarity	NPC167546
0.8443	Intermediate Similarity	NPC225774
0.8443	Intermediate Similarity	NPC16805
0.8443	Intermediate Similarity	NPC231198
0.8443	Intermediate Similarity	NPC302527
0.8439	Intermediate Similarity	NPC474506
0.8439	Intermediate Similarity	NPC32413
0.843	Intermediate Similarity	NPC23219
0.8415	Intermediate Similarity	NPC147091
0.8415	Intermediate Similarity	NPC180756
0.8415	Intermediate Similarity	NPC323443
0.8393	Intermediate Similarity	NPC219341
0.8393	Intermediate Similarity	NPC13916
0.8393	Intermediate Similarity	NPC264850
0.8391	Intermediate Similarity	NPC102760
0.8382	Intermediate Similarity	NPC258695
0.8382	Intermediate Similarity	NPC470879
0.8372	Intermediate Similarity	NPC112575
0.8365	Intermediate Similarity	NPC130926
0.8362	Intermediate Similarity	NPC281581
0.8354	Intermediate Similarity	NPC93593
0.8344	Intermediate Similarity	NPC223124
0.8333	Intermediate Similarity	NPC232514
0.8333	Intermediate Similarity	NPC276944
0.8333	Intermediate Similarity	NPC24465
0.8333	Intermediate Similarity	NPC238530
0.8315	Intermediate Similarity	NPC473716
0.8315	Intermediate Similarity	NPC475597
0.8314	Intermediate Similarity	NPC49353
0.8313	Intermediate Similarity	NPC477080
0.8306	Intermediate Similarity	NPC2173
0.8306	Intermediate Similarity	NPC119818
0.8306	Intermediate Similarity	NPC328700
0.8306	Intermediate Similarity	NPC202771
0.8294	Intermediate Similarity	NPC83198
0.8294	Intermediate Similarity	NPC204908
0.8286	Intermediate Similarity	NPC275132
0.8268	Intermediate Similarity	NPC24260
0.8263	Intermediate Similarity	NPC205167
0.8263	Intermediate Similarity	NPC249274
0.8263	Intermediate Similarity	NPC477559
0.8263	Intermediate Similarity	NPC160298
0.8263	Intermediate Similarity	NPC306902
0.8263	Intermediate Similarity	NPC4304
0.8263	Intermediate Similarity	NPC232924
0.8263	Intermediate Similarity	NPC266753
0.8261	Intermediate Similarity	NPC51957
0.8261	Intermediate Similarity	NPC476144
0.8261	Intermediate Similarity	NPC106295
0.8261	Intermediate Similarity	NPC16107
0.8261	Intermediate Similarity	NPC210437
0.8249	Intermediate Similarity	NPC230098
0.8228	Intermediate Similarity	NPC213206
0.8228	Intermediate Similarity	NPC188163
0.8228	Intermediate Similarity	NPC474915
0.8228	Intermediate Similarity	NPC328750
0.821	Intermediate Similarity	NPC7467
0.8205	Intermediate Similarity	NPC7018
0.8204	Intermediate Similarity	NPC92191
0.8204	Intermediate Similarity	NPC59028
0.8198	Intermediate Similarity	NPC63646
0.8198	Intermediate Similarity	NPC115284
0.8198	Intermediate Similarity	NPC276890
0.8198	Intermediate Similarity	NPC76682
0.8198	Intermediate Similarity	NPC198498
0.8198	Intermediate Similarity	NPC227060
0.8198	Intermediate Similarity	NPC10908
0.8198	Intermediate Similarity	NPC317145
0.8198	Intermediate Similarity	NPC317439
0.8182	Intermediate Similarity	NPC248642
0.8171	Intermediate Similarity	NPC126284
0.8167	Intermediate Similarity	NPC117717
0.8165	Intermediate Similarity	NPC314682
0.8161	Intermediate Similarity	NPC283999
0.8156	Intermediate Similarity	NPC82763
0.815	Intermediate Similarity	NPC152680
0.815	Intermediate Similarity	NPC12424
0.815	Intermediate Similarity	NPC190783
0.815	Intermediate Similarity	NPC129518
0.815	Intermediate Similarity	NPC251580
0.815	Intermediate Similarity	NPC41376
0.815	Intermediate Similarity	NPC232386
0.8146	Intermediate Similarity	NPC57036
0.8144	Intermediate Similarity	NPC78359
0.8144	Intermediate Similarity	NPC148014
0.8144	Intermediate Similarity	NPC40389
0.8144	Intermediate Similarity	NPC129603
0.8144	Intermediate Similarity	NPC315707
0.8144	Intermediate Similarity	NPC65490
0.814	Intermediate Similarity	NPC6152
0.8136	Intermediate Similarity	NPC156576
0.8133	Intermediate Similarity	NPC244112
0.8133	Intermediate Similarity	NPC76079
0.8114	Intermediate Similarity	NPC114364
0.8114	Intermediate Similarity	NPC320223
0.811	Intermediate Similarity	NPC274026
0.8103	Intermediate Similarity	NPC128560
0.8103	Intermediate Similarity	NPC229166
0.8103	Intermediate Similarity	NPC199465
0.8101	Intermediate Similarity	NPC186546
0.8101	Intermediate Similarity	NPC476576
0.8095	Intermediate Similarity	NPC111485
0.8095	Intermediate Similarity	NPC106786
0.8092	Intermediate Similarity	NPC10871
0.8087	Intermediate Similarity	NPC124302
0.8087	Intermediate Similarity	NPC70290
0.8087	Intermediate Similarity	NPC14622
0.8087	Intermediate Similarity	NPC46744
0.8087	Intermediate Similarity	NPC73020
0.8087	Intermediate Similarity	NPC215098
0.807	Intermediate Similarity	NPC124657
0.8068	Intermediate Similarity	NPC99179
0.8068	Intermediate Similarity	NPC267408
0.8059	Intermediate Similarity	NPC59567
0.8057	Intermediate Similarity	NPC293093
0.8046	Intermediate Similarity	NPC228040
0.8037	Intermediate Similarity	NPC476151
0.8036	Intermediate Similarity	NPC476572
0.8024	Intermediate Similarity	NPC325871
0.8024	Intermediate Similarity	NPC123323
0.8024	Intermediate Similarity	NPC99659
0.8023	Intermediate Similarity	NPC298979
0.8023	Intermediate Similarity	NPC204947
0.8022	Intermediate Similarity	NPC471113
0.8012	Intermediate Similarity	NPC133011
0.8012	Intermediate Similarity	NPC136860
0.8012	Intermediate Similarity	NPC476567
0.8012	Intermediate Similarity	NPC82285
0.8012	Intermediate Similarity	NPC128019
0.8	Intermediate Similarity	NPC237579
0.8	Intermediate Similarity	NPC314100
0.8	Intermediate Similarity	NPC226652
0.8	Intermediate Similarity	NPC120671
0.8	Intermediate Similarity	NPC72788

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 NPC75958 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	213
0.1-0.2	705
0.2-0.3	977
0.3-0.4	2627
0.4-0.5	2524
0.5-0.6	1524
0.6-0.7	466
0.7-0.8	103
0.8-0.85	11
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8306	Intermediate Similarity	NPD5006	Approved
0.8306	Intermediate Similarity	NPD5005	Approved
0.8261	Intermediate Similarity	NPD4584	Approved
0.8256	Intermediate Similarity	NPD8156	Discontinued
0.8228	Intermediate Similarity	NPD4664	Clinical (unspecified phase)
0.8198	Intermediate Similarity	NPD8251	Approved
0.8198	Intermediate Similarity	NPD8252	Approved
0.8198	Intermediate Similarity	NPD8099	Discontinued
0.8176	Intermediate Similarity	NPD6071	Discontinued
0.8144	Intermediate Similarity	NPD2560	Approved
0.8144	Intermediate Similarity	NPD2563	Approved
0.8095	Intermediate Similarity	NPD6788	Approved
0.8087	Intermediate Similarity	NPD4420	Approved
0.8081	Intermediate Similarity	NPD4481	Phase 3
0.8075	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.7927	Intermediate Similarity	NPD1424	Approved
0.7919	Intermediate Similarity	NPD2970	Approved
0.7919	Intermediate Similarity	NPD2969	Approved
0.7877	Intermediate Similarity	NPD8054	Approved
0.7877	Intermediate Similarity	NPD8053	Approved
0.7861	Intermediate Similarity	NPD3051	Approved
0.7771	Intermediate Similarity	NPD2489	Approved
0.7771	Intermediate Similarity	NPD27	Approved
0.7751	Intermediate Similarity	NPD4772	Phase 2
0.7751	Intermediate Similarity	NPD4773	Phase 2
0.7744	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7697	Intermediate Similarity	NPD7124	Phase 2
0.7697	Intermediate Similarity	NPD6783	Clinical (unspecified phase)
0.767	Intermediate Similarity	NPD2898	Approved
0.765	Intermediate Similarity	NPD7906	Approved
0.7633	Intermediate Similarity	NPD7261	Clinical (unspecified phase)
0.7633	Intermediate Similarity	NPD4017	Approved
0.7624	Intermediate Similarity	NPD7312	Approved
0.7624	Intermediate Similarity	NPD7310	Approved
0.7624	Intermediate Similarity	NPD7313	Approved
0.7624	Intermediate Similarity	NPD7311	Approved
0.7619	Intermediate Similarity	NPD3641	Approved
0.7619	Intermediate Similarity	NPD3640	Phase 3
0.7619	Intermediate Similarity	NPD3639	Approved
0.76	Intermediate Similarity	NPD6107	Approved
0.7582	Intermediate Similarity	NPD7309	Approved
0.7529	Intermediate Similarity	NPD4055	Discovery
0.7527	Intermediate Similarity	NPD4578	Approved
0.7527	Intermediate Similarity	NPD4577	Approved
0.7515	Intermediate Similarity	NPD6030	Approved
0.7515	Intermediate Similarity	NPD6031	Approved
0.75	Intermediate Similarity	NPD7298	Approved
0.75	Intermediate Similarity	NPD4663	Approved
0.7484	Intermediate Similarity	NPD2669	Clinical (unspecified phase)
0.7471	Intermediate Similarity	NPD4210	Discontinued
0.7457	Intermediate Similarity	NPD6818	Clinical (unspecified phase)
0.7432	Intermediate Similarity	NPD7281	Phase 3
0.7432	Intermediate Similarity	NPD2971	Approved
0.7432	Intermediate Similarity	NPD7280	Phase 3
0.7432	Intermediate Similarity	NPD2968	Approved
0.7423	Intermediate Similarity	NPD6111	Discontinued
0.741	Intermediate Similarity	NPD4236	Phase 3
0.741	Intermediate Similarity	NPD4237	Approved
0.7407	Intermediate Similarity	NPD5582	Discontinued
0.7399	Intermediate Similarity	NPD3383	Approved
0.7399	Intermediate Similarity	NPD3384	Approved
0.7399	Intermediate Similarity	NPD3382	Approved
0.7391	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD554	Clinical (unspecified phase)
0.7382	Intermediate Similarity	NPD8095	Phase 1
0.7378	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7378	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.736	Intermediate Similarity	NPD4166	Phase 2
0.7356	Intermediate Similarity	NPD4585	Approved
0.7356	Intermediate Similarity	NPD2978	Approved
0.7356	Intermediate Similarity	NPD2977	Approved
0.7348	Intermediate Similarity	NPD5313	Approved
0.7348	Intermediate Similarity	NPD5312	Approved
0.7345	Intermediate Similarity	NPD5677	Discontinued
0.734	Intermediate Similarity	NPD7296	Approved
0.733	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7326	Intermediate Similarity	NPD4005	Discontinued
0.7321	Intermediate Similarity	NPD5241	Discontinued
0.7317	Intermediate Similarity	NPD2200	Suspended
0.7277	Intermediate Similarity	NPD2974	Approved
0.7277	Intermediate Similarity	NPD2973	Approved
0.7277	Intermediate Similarity	NPD2975	Approved
0.7257	Intermediate Similarity	NPD5772	Approved
0.7257	Intermediate Similarity	NPD5773	Approved
0.7247	Intermediate Similarity	NPD7201	Clinical (unspecified phase)
0.7235	Intermediate Similarity	NPD5297	Approved
0.7232	Intermediate Similarity	NPD7833	Phase 2
0.7232	Intermediate Similarity	NPD7831	Phase 2
0.7232	Intermediate Similarity	NPD7832	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD5718	Phase 2
0.7212	Intermediate Similarity	NPD6895	Approved
0.7212	Intermediate Similarity	NPD6896	Approved
0.7209	Intermediate Similarity	NPD4727	Phase 1
0.7202	Intermediate Similarity	NPD5177	Phase 3
0.7193	Intermediate Similarity	NPD1754	Clinical (unspecified phase)
0.7167	Intermediate Similarity	NPD4010	Discontinued
0.7165	Intermediate Similarity	NPD4580	Approved
0.7156	Intermediate Similarity	NPD6625	Approved
0.7152	Intermediate Similarity	NPD2492	Phase 1
0.7143	Intermediate Similarity	NPD5089	Approved
0.7143	Intermediate Similarity	NPD5090	Approved
0.7135	Intermediate Similarity	NPD7667	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD5604	Discontinued
0.7135	Intermediate Similarity	NPD3124	Discontinued
0.7128	Intermediate Similarity	NPD3450	Approved
0.7128	Intermediate Similarity	NPD2493	Approved
0.7128	Intermediate Similarity	NPD3452	Approved
0.7128	Intermediate Similarity	NPD2494	Approved
0.7114	Intermediate Similarity	NPD7827	Phase 1
0.7113	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.711	Intermediate Similarity	NPD5976	Discontinued
0.7105	Intermediate Similarity	NPD2490	Approved
0.7105	Intermediate Similarity	NPD2488	Approved
0.7099	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.709	Intermediate Similarity	NPD6842	Approved
0.709	Intermediate Similarity	NPD6841	Approved
0.709	Intermediate Similarity	NPD6843	Phase 3
0.709	Intermediate Similarity	NPD7243	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD3705	Approved
0.7081	Intermediate Similarity	NPD6996	Clinical (unspecified phase)
0.7077	Intermediate Similarity	NPD4107	Approved
0.7073	Intermediate Similarity	NPD4475	Approved
0.7073	Intermediate Similarity	NPD4474	Approved
0.7059	Intermediate Similarity	NPD7466	Approved
0.7041	Intermediate Similarity	NPD1372	Clinical (unspecified phase)
0.7033	Intermediate Similarity	NPD6688	Approved
0.7033	Intermediate Similarity	NPD6687	Approved
0.7033	Intermediate Similarity	NPD5242	Approved
0.703	Intermediate Similarity	NPD3110	Approved
0.703	Intermediate Similarity	NPD3109	Approved
0.703	Intermediate Similarity	NPD2238	Phase 2
0.702	Intermediate Similarity	NPD4583	Approved
0.702	Intermediate Similarity	NPD4582	Approved
0.7017	Intermediate Similarity	NPD7802	Discontinued
0.7005	Intermediate Similarity	NPD8453	Clinical (unspecified phase)
0.7005	Intermediate Similarity	NPD7549	Discontinued
0.6995	Remote Similarity	NPD6365	Clinical (unspecified phase)
0.6989	Remote Similarity	NPD4675	Approved
0.6989	Remote Similarity	NPD6297	Approved
0.6989	Remote Similarity	NPD4678	Approved
0.6982	Remote Similarity	NPD1375	Discontinued
0.6971	Remote Similarity	NPD6997	Phase 2
0.697	Remote Similarity	NPD4004	Approved
0.697	Remote Similarity	NPD4002	Approved
0.6963	Remote Similarity	NPD7235	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD5754	Discontinued
0.6954	Remote Similarity	NPD4482	Phase 3
0.6954	Remote Similarity	NPD3647	Clinical (unspecified phase)
0.6931	Remote Similarity	NPD6853	Approved
0.6931	Remote Similarity	NPD6851	Approved
0.6927	Remote Similarity	NPD7047	Phase 3
0.6927	Remote Similarity	NPD5977	Approved
0.6927	Remote Similarity	NPD5525	Clinical (unspecified phase)
0.6927	Remote Similarity	NPD5978	Approved
0.691	Remote Similarity	NPD7945	Clinical (unspecified phase)
0.6906	Remote Similarity	NPD7400	Phase 3
0.6901	Remote Similarity	NPD3060	Approved
0.6889	Remote Similarity	NPD4967	Phase 2
0.6889	Remote Similarity	NPD4965	Approved
0.6889	Remote Similarity	NPD4966	Approved
0.6878	Remote Similarity	NPD3534	Clinical (unspecified phase)
0.6865	Remote Similarity	NPD5602	Clinical (unspecified phase)
0.686	Remote Similarity	NPD6748	Discontinued
0.686	Remote Similarity	NPD6658	Clinical (unspecified phase)
0.6845	Remote Similarity	NPD3885	Approved
0.6839	Remote Similarity	NPD2421	Approved
0.6839	Remote Similarity	NPD2420	Approved
0.6839	Remote Similarity	NPD7213	Phase 3
0.6839	Remote Similarity	NPD7212	Phase 2
0.6837	Remote Similarity	NPD6621	Clinical (unspecified phase)
0.6836	Remote Similarity	NPD8158	Clinical (unspecified phase)
0.6834	Remote Similarity	NPD3057	Approved
0.6832	Remote Similarity	NPD4859	Phase 1
0.6816	Remote Similarity	NPD37	Approved
0.6816	Remote Similarity	NPD7607	Clinical (unspecified phase)
0.6813	Remote Similarity	NPD6234	Discontinued
0.6802	Remote Similarity	NPD4162	Approved
0.68	Remote Similarity	NPD7019	Approved
0.68	Remote Similarity	NPD7447	Phase 1
0.68	Remote Similarity	NPD7020	Approved
0.6796	Remote Similarity	NPD4581	Clinical (unspecified phase)
0.678	Remote Similarity	NPD3816	Phase 1
0.678	Remote Similarity	NPD3815	Phase 1
0.6778	Remote Similarity	NPD6668	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD3489	Phase 3
0.6772	Remote Similarity	NPD7149	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD1753	Discontinued
0.6765	Remote Similarity	NPD4108	Discontinued
0.6763	Remote Similarity	NPD3977	Clinical (unspecified phase)
0.676	Remote Similarity	NPD6072	Discontinued
0.676	Remote Similarity	NPD7109	Clinical (unspecified phase)
0.676	Remote Similarity	NPD6386	Approved
0.676	Remote Similarity	NPD6385	Approved
0.676	Remote Similarity	NPD7110	Phase 1
0.6759	Remote Similarity	NPD6723	Discontinued
0.6753	Remote Similarity	NPD3808	Clinical (unspecified phase)
0.675	Remote Similarity	NPD3533	Approved
0.675	Remote Similarity	NPD2972	Approved
0.6743	Remote Similarity	NPD7837	Clinical (unspecified phase)
0.674	Remote Similarity	NPD5353	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