NPASS Compound

Structure

CID179704 OpenBabel06191715552D 26 30 0 0 0 0 0 0 0 0999 V2000 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 2.0000 0.0000 C 0 0 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 -0.8660 -2.5000 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 -3.4641 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 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 4.1369 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 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 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -2.5000 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 0.0000 -1.0000 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 -0.0000 -0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.5491 -2.8090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.5491 -1.1910 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 22 1 0 0 0 0 2 23 1 0 0 0 0 3 24 1 0 0 0 0 4 5 2 0 0 0 0 4 12 1 0 0 0 0 5 14 1 0 0 0 0 6 7 1 0 0 0 0 6 13 2 0 0 0 0 7 17 2 0 0 0 0 8 12 2 0 0 0 0 8 18 1 0 0 0 0 9 15 2 0 0 0 0 9 19 1 0 0 0 0 10 16 1 0 0 0 0 10 22 1 0 0 0 0 11 25 1 0 0 0 0 11 26 1 0 0 0 0 12 15 1 0 0 0 0 13 14 1 0 0 0 0 13 16 1 0 0 0 0 14 20 2 0 0 0 0 15 20 1 0 0 0 0 16 21 2 0 0 0 0 17 21 1 0 0 0 0 17 23 1 0 0 0 0 18 19 2 0 0 0 0 18 25 1 0 0 0 0 19 26 1 0 0 0 0 20 22 1 0 0 0 0 21 24 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	349.13
Volume:	354.056
LogP:	4.971
LogD:	3.73
LogS:	-7.066
# 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:	0.693
Synthetic Accessibility Score:	2.603
Fsp3:	0.238
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.973
MDCK Permeability:	3.680610461742617e-05
Pgp-inhibitor:	0.272
Pgp-substrate:	0.979
Human Intestinal Absorption (HIA):	0.002
20% Bioavailability (F20%):	0.004
30% Bioavailability (F30%):	0.217

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.264
Plasma Protein Binding (PPB):	92.22492980957031%
Volume Distribution (VD):	0.647
Pgp-substrate:	1.816652536392212%

ADMET: Metabolism

CYP1A2-inhibitor:	0.979
CYP1A2-substrate:	0.894
CYP2C19-inhibitor:	0.975
CYP2C19-substrate:	0.626
CYP2C9-inhibitor:	0.751
CYP2C9-substrate:	0.923
CYP2D6-inhibitor:	0.976
CYP2D6-substrate:	0.93
CYP3A4-inhibitor:	0.877
CYP3A4-substrate:	0.437

ADMET: Excretion

Clearance (CL):	13.572
Half-life (T1/2):	0.151

ADMET: Toxicity

hERG Blockers:	0.321
Human Hepatotoxicity (H-HT):	0.107
Drug-inuced Liver Injury (DILI):	0.902
AMES Toxicity:	0.764
Rat Oral Acute Toxicity:	0.072
Maximum Recommended Daily Dose:	0.71
Skin Sensitization:	0.858
Carcinogencity:	0.919
Eye Corrosion:	0.003
Eye Irritation:	0.033
Respiratory Toxicity:	0.897

Download Data

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

Natural Product: NPC179704

Natural Product ID:	NPC179704
*Common Name:**	Dihydrochelerythrine
IUPAC Name:	1,2-dimethoxy-12-methyl-13H-[1,3]benzodioxolo[5,6-c]phenanthridine
Synonyms:	Dihydrochelerythrine
Standard InCHIKey:	ALZAZMCIBRHMFF-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C21H19NO4/c1-22-10-16-13(6-7-17(23-2)21(16)24-3)14-5-4-12-8-18-19(26-11-25-18)9-15(12)20(14)22/h4-9H,10-11H2,1-3H3
SMILES:	COc1c(OC)ccc2c1CN(C)c1c2ccc2c1cc1OCOc1c2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL400359
PubChem CID:	485077
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids and derivatives [CHEMONTID:0002665] Benzophenanthridine alkaloids [CHEMONTID:0002667] Dihydrobenzophenanthridine 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
NPO24024	Fusarium semitectum	Species	Nectriaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10978211]
NPO13757	Coptis japonica	Species	Ranunculaceae	Eukaryota	rhizomes	n.a.	n.a.	PMID[11000020]
NPO21424	Garcinia xanthochymus	Species	Clusiaceae	Eukaryota	n.a.	xylem	n.a.	PMID[14600386]
NPO21424	Garcinia xanthochymus	Species	Clusiaceae	Eukaryota	fruits	n.a.	n.a.	PMID[15787435]
NPO13278	Strychnos spinosa	Species	Loganiaceae	Eukaryota	Leaves	n.a.	n.a.	PMID[17637068]
NPO2842	Garcinia lucida	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17880175]
NPO15233	Balanophora japonica	Species	Balanophoraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18302336]
NPO9650	Zanthoxylum nitidum	Species	Rutaceae	Eukaryota	stem bark	n.a.	n.a.	PMID[18303853]
NPO9650	Zanthoxylum nitidum	Species	Rutaceae	Eukaryota	Stems; Barks	n.a.	n.a.	PMID[18303853]
NPO13757	Coptis japonica	Species	Ranunculaceae	Eukaryota	n.a.	rhizome	n.a.	PMID[21401114]
NPO5470	Cynoglossum amabile	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22432912]
NPO24024	Fusarium semitectum	Species	Nectriaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22439674]
NPO8101	Rehmannia glutinosa	Species	Orobanchaceae	Eukaryota	Roots	n.a.	n.a.	PMID[22916954]
NPO5315	Zanthoxylum bungeanum	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24175626]
NPO7213	Toddalia asiatica	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24597921]
NPO2330	Alchornea cordifolia	Species	Euphorbiaceae	Eukaryota	n.a.	stem	n.a.	PMID[26724423]
NPO2330	Alchornea cordifolia	Species	Euphorbiaceae	Eukaryota	n.a.	root	n.a.	PMID[26724423]
NPO18823	Colysis pothifolia	Species	Polypodiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26731047]
NPO9650	Zanthoxylum nitidum	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5470	Cynoglossum amabile	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11457	Chelidonium majus	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO13757	Coptis japonica	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO20871	Pueraria tuberosa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8101	Rehmannia glutinosa	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15233	Balanophora japonica	Species	Balanophoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO21424	Garcinia xanthochymus	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5315	Zanthoxylum bungeanum	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO21004	Nicotiana plumbaginifolia	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7213	Toddalia asiatica	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO13278	Strychnos spinosa	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO22622	Coptis deltoidea	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5649	Coptis chinensis	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8101	Rehmannia glutinosa	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22622	Coptis deltoidea	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5315	Zanthoxylum bungeanum	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20871	Pueraria tuberosa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10098	Glycosmis pseudoracemosa	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13278	Strychnos spinosa	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11457	Chelidonium majus	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5470	Cynoglossum amabile	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21424	Garcinia xanthochymus	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7213	Toddalia asiatica	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9650	Zanthoxylum nitidum	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12487	Juniperus horizontalis	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15233	Balanophora japonica	Species	Balanophoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5649	Coptis chinensis	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23772	Tetradium glabrifolium	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13757	Coptis japonica	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21004	Nicotiana plumbaginifolia	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9650	Zanthoxylum nitidum	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO5470	Cynoglossum amabile	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO11457	Chelidonium majus	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO5649	Coptis chinensis	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO5315	Zanthoxylum bungeanum	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO7213	Toddalia asiatica	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO20871	Pueraria tuberosa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO8101	Rehmannia glutinosa	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO29008	Coptis teeta	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO13757	Coptis japonica	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO11457	Chelidonium majus	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO22622	Coptis deltoidea	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO5649	Coptis chinensis	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO5315	Zanthoxylum bungeanum	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO8101	Rehmannia glutinosa	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO9650	Zanthoxylum nitidum	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO13757	Coptis japonica	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17489	Myoporum acuminatum	Species	Scrophulariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18823	Colysis pothifolia	Species	Polypodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29008	Coptis teeta	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20271	Canarina canariensis	Species	Campanulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24024	Fusarium semitectum	Species	Nectriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14947	Lathyrus tingitanus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5398	Peucedanum oroselinum	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15221	Crambe fruticosa	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13216	Streptomyces pulveraceus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO21677	Liatris aspera	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6906	Atalantia wightii	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7521	Hygrophorus eburneus	Species	Hygrophoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7213	Toddalia asiatica	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19340	Orobanche caerulescens	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15145	Rauvolfia salicifolia	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13278	Strychnos spinosa	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5315	Zanthoxylum bungeanum	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3761	Plectosphaerella cucumerina	Species	Plectosphaerellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16801	Cota tinctoria	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21230	Heterodermia obscurata	Species	Physciaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20871	Pueraria tuberosa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21424	Garcinia xanthochymus	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18613	Commiphora erlangeriana	Species	Burseraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10098	Glycosmis pseudoracemosa	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3965	Corynanthe pachyceras	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21143	Cryptocarya canelilla	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18580	Diabelia spathulata	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11430	Inula grantioides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15329	Rhizoplaca baranowii	Species	Lecanoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15233	Balanophora japonica	Species	Balanophoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1759	Alexandrium excavatum	Species	Gonyaulacaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22622	Coptis deltoidea	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14526	Plectranthus caninus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14713	Bauhinia retusa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13647	Calcarisporium thermophilum	Species	n.a.	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13848	Amomum daniellii	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8315	Wunderlichia crulsiana	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18873.2	Salmonella enterica subsp. enterica serovar bovismorbificans	Subspecies	Enterobacteriaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO2330	Alchornea cordifolia	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8101	Rehmannia glutinosa	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9650	Zanthoxylum nitidum	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5649	Coptis chinensis	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25619	Vitex divaricata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5470	Cynoglossum amabile	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23772	Tetradium glabrifolium	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2842	Garcinia lucida	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12487	Juniperus horizontalis	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21004	Nicotiana plumbaginifolia	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18421	Tachardia lacca	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO1109	Corydalis persica	Species	Papaveraceae	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	9
Others	13

Activity Type	# Activity
Cell Line	7
Individual Protein	1
Organism	8
Others	6

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT189	Cell Line	Vero	Chlorocebus aethiops	IC50	=	35400.0	nM	PMID[564724]
NPT1592	Individual Protein	Dipeptidyl peptidase IV	Homo sapiens	IC50	=	56230.0	nM	PMID[564727]
NPT393	Cell Line	HCT-116	Homo sapiens	IC50	>	10000.0	nM	PMID[564728]
NPT116	Cell Line	HL-60	Homo sapiens	IC50	>	10000.0	nM	PMID[564728]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	Inhibition	=	8.65	%	PMID[564729]
NPT762	Cell Line	A-431	Homo sapiens	Inhibition	=	30.39	%	PMID[564729]
NPT306	Cell Line	PC-3	Homo sapiens	GI	=	26.6	%	PMID[564730]
NPT148	Cell Line	HCT-15	Homo sapiens	GI	=	56.5	%	PMID[564730]
NPT471	Organism	Trypanosoma brucei brucei	Trypanosoma brucei brucei	IC50	=	800.0	nM	PMID[564724]
NPT633	Organism	Leishmania donovani	Leishmania donovani	IC50	=	2000.0	nM	PMID[564724]
NPT633	Organism	Leishmania donovani	Leishmania donovani	Inhibition	=	100.0	%	PMID[564724]
NPT633	Organism	Leishmania donovani	Leishmania donovani	Inhibition	=	89.0	%	PMID[564724]
NPT633	Organism	Leishmania donovani	Leishmania donovani	Inhibition	=	36.0	%	PMID[564724]
NPT633	Organism	Leishmania donovani	Leishmania donovani	Activity	=	70.9	%	PMID[564724]
NPT963	Organism	Hepatitis B virus	Hepatitis B virus	IC50	<	50.0	nM	PMID[564726]
NPT2	Others	Unspecified		Delta Tm	=	24.0	degrees C	PMID[564729]
NPT2	Others	Unspecified		Delta Tm	=	17.6	degrees C	PMID[564729]
NPT2	Others	Unspecified		Delta Tm	=	-1.0	degrees C	PMID[564729]
NPT2	Others	Unspecified		K	=	5.5	10'5/M	PMID[564729]
NPT2	Others	Unspecified		IC50	=	5800.0	nM	PMID[564729]
NPT2	Others	Unspecified		GI	=	16.0	%	PMID[564730]

☑ 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 NPC179704 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	481
0.1-0.2	2374
0.2-0.3	11228
0.3-0.4	6151
0.4-0.5	10433
0.5-0.6	9797
0.6-0.7	1537
0.7-0.8	567
0.8-0.85	94
0.85-0.9	20
0.9-0.95	10
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
0.9816	High Similarity	NPC287588
0.9581	High Similarity	NPC249405
0.9532	High Similarity	NPC302001
0.9471	High Similarity	NPC312531
0.9471	High Similarity	NPC474904
0.9314	High Similarity	NPC23080
0.9314	High Similarity	NPC193906
0.931	High Similarity	NPC162653
0.9222	High Similarity	NPC285941
0.9059	High Similarity	NPC190461
0.9045	High Similarity	NPC212163
0.897	High Similarity	NPC24954
0.8944	High Similarity	NPC295676
0.8909	High Similarity	NPC266753
0.8909	High Similarity	NPC160298
0.8909	High Similarity	NPC232924
0.8909	High Similarity	NPC306902
0.8909	High Similarity	NPC477559
0.8851	High Similarity	NPC33902
0.8851	High Similarity	NPC276674
0.881	High Similarity	NPC476432
0.881	High Similarity	NPC24264
0.8798	High Similarity	NPC156728
0.8798	High Similarity	NPC244606
0.8757	High Similarity	NPC247389
0.875	High Similarity	NPC302527
0.875	High Similarity	NPC16805
0.875	High Similarity	NPC225774
0.875	High Similarity	NPC167546
0.875	High Similarity	NPC320088
0.8698	High Similarity	NPC219341
0.8647	High Similarity	NPC210918
0.8647	High Similarity	NPC298979
0.8596	High Similarity	NPC241055
0.8588	High Similarity	NPC304659
0.8588	High Similarity	NPC86144
0.8571	High Similarity	NPC17677
0.8556	High Similarity	NPC78284
0.8554	High Similarity	NPC138487
0.8554	High Similarity	NPC93593
0.8554	High Similarity	NPC216459
0.8554	High Similarity	NPC41178
0.8529	High Similarity	NPC168409
0.8503	High Similarity	NPC146288
0.8497	Intermediate Similarity	NPC149090
0.8497	Intermediate Similarity	NPC19520
0.8485	Intermediate Similarity	NPC326316
0.8485	Intermediate Similarity	NPC81733
0.8471	Intermediate Similarity	NPC189470
0.8446	Intermediate Similarity	NPC23614
0.8446	Intermediate Similarity	NPC100079
0.8443	Intermediate Similarity	NPC76079
0.8439	Intermediate Similarity	NPC6152
0.8415	Intermediate Similarity	NPC475959
0.8409	Intermediate Similarity	NPC320223
0.8409	Intermediate Similarity	NPC114364
0.84	Intermediate Similarity	NPC229166
0.84	Intermediate Similarity	NPC199465
0.84	Intermediate Similarity	NPC128560
0.8393	Intermediate Similarity	NPC234392
0.8393	Intermediate Similarity	NPC31311
0.8385	Intermediate Similarity	NPC235076
0.8364	Intermediate Similarity	NPC219162
0.8344	Intermediate Similarity	NPC145304
0.8343	Intermediate Similarity	NPC476572
0.8333	Intermediate Similarity	NPC325871
0.8333	Intermediate Similarity	NPC271215
0.8333	Intermediate Similarity	NPC99659
0.8333	Intermediate Similarity	NPC244112
0.8333	Intermediate Similarity	NPC149471
0.8333	Intermediate Similarity	NPC471489
0.8308	Intermediate Similarity	NPC46451
0.8305	Intermediate Similarity	NPC294790
0.8305	Intermediate Similarity	NPC118633
0.8305	Intermediate Similarity	NPC148693
0.8303	Intermediate Similarity	NPC130941
0.8294	Intermediate Similarity	NPC477080
0.829	Intermediate Similarity	NPC55470
0.8272	Intermediate Similarity	NPC188420
0.8268	Intermediate Similarity	NPC248642
0.8258	Intermediate Similarity	NPC126284
0.8253	Intermediate Similarity	NPC211296
0.8242	Intermediate Similarity	NPC90844
0.8242	Intermediate Similarity	NPC253883
0.8242	Intermediate Similarity	NPC95075
0.8229	Intermediate Similarity	NPC152212
0.8222	Intermediate Similarity	NPC156576
0.8214	Intermediate Similarity	NPC233029
0.8214	Intermediate Similarity	NPC210148
0.8212	Intermediate Similarity	NPC474506
0.8212	Intermediate Similarity	NPC32413
0.8208	Intermediate Similarity	NPC232514
0.8208	Intermediate Similarity	NPC238530
0.8208	Intermediate Similarity	NPC276944
0.8202	Intermediate Similarity	NPC23219
0.8176	Intermediate Similarity	NPC170503
0.8176	Intermediate Similarity	NPC126519
0.8176	Intermediate Similarity	NPC203784
0.8167	Intermediate Similarity	NPC116284
0.8156	Intermediate Similarity	NPC258695
0.8156	Intermediate Similarity	NPC470879
0.8156	Intermediate Similarity	NPC267408
0.8146	Intermediate Similarity	NPC112575
0.8144	Intermediate Similarity	NPC92541
0.814	Intermediate Similarity	NPC27410
0.814	Intermediate Similarity	NPC166014
0.8133	Intermediate Similarity	NPC16107
0.8133	Intermediate Similarity	NPC51957
0.8133	Intermediate Similarity	NPC476144
0.8133	Intermediate Similarity	NPC210437
0.8133	Intermediate Similarity	NPC106295
0.8132	Intermediate Similarity	NPC477186
0.8128	Intermediate Similarity	NPC5374
0.8122	Intermediate Similarity	NPC135772
0.8111	Intermediate Similarity	NPC476574
0.8111	Intermediate Similarity	NPC477561
0.8111	Intermediate Similarity	NPC155442
0.8111	Intermediate Similarity	NPC312918
0.8092	Intermediate Similarity	NPC60186
0.809	Intermediate Similarity	NPC477558
0.809	Intermediate Similarity	NPC118121
0.8087	Intermediate Similarity	NPC237579
0.8084	Intermediate Similarity	NPC7467
0.8046	Intermediate Similarity	NPC324144
0.8046	Intermediate Similarity	NPC233650
0.8033	Intermediate Similarity	NPC214116
0.8024	Intermediate Similarity	NPC144863
0.8011	Intermediate Similarity	NPC117188
0.8011	Intermediate Similarity	NPC205421
0.8011	Intermediate Similarity	NPC145832
0.8011	Intermediate Similarity	NPC12053
0.8011	Intermediate Similarity	NPC471604
0.8011	Intermediate Similarity	NPC81218
0.8011	Intermediate Similarity	NPC474931
0.8011	Intermediate Similarity	NPC158376
0.8011	Intermediate Similarity	NPC306555
0.8	Intermediate Similarity	NPC136508
0.8	Intermediate Similarity	NPC477563
0.8	Intermediate Similarity	NPC212794
0.8	Intermediate Similarity	NPC26601
0.8	Intermediate Similarity	NPC13504
0.8	Intermediate Similarity	NPC251160
0.8	Intermediate Similarity	NPC306843
0.8	Intermediate Similarity	NPC196447
0.8	Intermediate Similarity	NPC148898
0.8	Intermediate Similarity	NPC253043
0.8	Intermediate Similarity	NPC96603
0.8	Intermediate Similarity	NPC134858
0.8	Intermediate Similarity	NPC78222
0.7989	Intermediate Similarity	NPC296742
0.7988	Intermediate Similarity	NPC188163
0.7988	Intermediate Similarity	NPC213206
0.7988	Intermediate Similarity	NPC474915
0.7988	Intermediate Similarity	NPC328750
0.798	Intermediate Similarity	NPC204446
0.7979	Intermediate Similarity	NPC71124
0.7977	Intermediate Similarity	NPC111485
0.7967	Intermediate Similarity	NPC275132
0.7965	Intermediate Similarity	NPC186063
0.7946	Intermediate Similarity	NPC82763
0.7935	Intermediate Similarity	NPC57036
0.7935	Intermediate Similarity	NPC224293
0.7933	Intermediate Similarity	NPC2314
0.7927	Intermediate Similarity	NPC308943
0.7927	Intermediate Similarity	NPC314682
0.7917	Intermediate Similarity	NPC268077
0.791	Intermediate Similarity	NPC150879
0.791	Intermediate Similarity	NPC210140
0.7907	Intermediate Similarity	NPC78733
0.7892	Intermediate Similarity	NPC112676
0.7892	Intermediate Similarity	NPC136860
0.7892	Intermediate Similarity	NPC476567
0.7892	Intermediate Similarity	NPC476576
0.7892	Intermediate Similarity	NPC128019
0.7892	Intermediate Similarity	NPC186546
0.788	Intermediate Similarity	NPC69213
0.7879	Intermediate Similarity	NPC470925
0.7869	Intermediate Similarity	NPC476575
0.7869	Intermediate Similarity	NPC73492
0.7869	Intermediate Similarity	NPC299990
0.7865	Intermediate Similarity	NPC207971
0.7861	Intermediate Similarity	NPC254957
0.7853	Intermediate Similarity	NPC476573
0.7853	Intermediate Similarity	NPC7018
0.7853	Intermediate Similarity	NPC35627
0.7853	Intermediate Similarity	NPC81247
0.7841	Intermediate Similarity	NPC1229
0.7817	Intermediate Similarity	NPC296482
0.7817	Intermediate Similarity	NPC202768
0.7817	Intermediate Similarity	NPC53069
0.7811	Intermediate Similarity	NPC476151
0.7809	Intermediate Similarity	NPC204947
0.7807	Intermediate Similarity	NPC79213
0.7803	Intermediate Similarity	NPC249797
0.7803	Intermediate Similarity	NPC193949
0.7803	Intermediate Similarity	NPC172765
0.7803	Intermediate Similarity	NPC5238
0.7803	Intermediate Similarity	NPC39701
0.7803	Intermediate Similarity	NPC110416
0.7803	Intermediate Similarity	NPC123323

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 NPC179704 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	262
0.1-0.2	801
0.2-0.3	1011
0.3-0.4	1533
0.4-0.5	2919
0.5-0.6	2007
0.6-0.7	541
0.7-0.8	74
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8308	Intermediate Similarity	NPD3763	Approved
0.8168	Intermediate Similarity	NPD4859	Phase 1
0.8133	Intermediate Similarity	NPD4584	Approved
0.7988	Intermediate Similarity	NPD4664	Clinical (unspecified phase)
0.7844	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.7817	Intermediate Similarity	NPD3816	Phase 1
0.7817	Intermediate Similarity	NPD3815	Phase 1
0.774	Intermediate Similarity	NPD6037	Discontinued
0.7692	Intermediate Similarity	NPD7479	Phase 2
0.7692	Intermediate Similarity	NPD6783	Clinical (unspecified phase)
0.7672	Intermediate Similarity	NPD7262	Phase 1
0.7542	Intermediate Similarity	NPD7201	Clinical (unspecified phase)
0.7529	Intermediate Similarity	NPD3301	Approved
0.7527	Intermediate Similarity	NPD5917	Clinical (unspecified phase)
0.7514	Intermediate Similarity	NPD6030	Approved
0.7514	Intermediate Similarity	NPD6031	Approved
0.75	Intermediate Similarity	NPD5582	Discontinued
0.7486	Intermediate Similarity	NPD8252	Approved
0.7486	Intermediate Similarity	NPD8251	Approved
0.7486	Intermediate Similarity	NPD8099	Discontinued
0.7473	Intermediate Similarity	NPD4481	Phase 3
0.7459	Intermediate Similarity	NPD3051	Approved
0.7446	Intermediate Similarity	NPD8156	Discontinued
0.7442	Intermediate Similarity	NPD2420	Approved
0.7442	Intermediate Similarity	NPD2421	Approved
0.7432	Intermediate Similarity	NPD5938	Phase 3
0.7432	Intermediate Similarity	NPD5602	Clinical (unspecified phase)
0.7429	Intermediate Similarity	NPD4017	Approved
0.7405	Intermediate Similarity	NPD3920	Phase 2
0.7401	Intermediate Similarity	NPD7298	Approved
0.7382	Intermediate Similarity	NPD6656	Clinical (unspecified phase)
0.7374	Intermediate Similarity	NPD6788	Approved
0.7358	Intermediate Similarity	NPD6493	Phase 3
0.7344	Intermediate Similarity	NPD3924	Approved
0.7344	Intermediate Similarity	NPD3923	Approved
0.7344	Intermediate Similarity	NPD3922	Approved
0.7344	Intermediate Similarity	NPD3921	Approved
0.7322	Intermediate Similarity	NPD2969	Approved
0.7322	Intermediate Similarity	NPD2970	Approved
0.7283	Intermediate Similarity	NPD6365	Clinical (unspecified phase)
0.7283	Intermediate Similarity	NPD6607	Clinical (unspecified phase)
0.7283	Intermediate Similarity	NPD27	Approved
0.7283	Intermediate Similarity	NPD2489	Approved
0.7278	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7258	Intermediate Similarity	NPD5600	Discontinued
0.7238	Intermediate Similarity	NPD7831	Phase 2
0.7238	Intermediate Similarity	NPD7832	Clinical (unspecified phase)
0.7238	Intermediate Similarity	NPD7833	Phase 2
0.7228	Intermediate Similarity	NPD4083	Discontinued
0.7216	Intermediate Similarity	NPD3641	Approved
0.7216	Intermediate Similarity	NPD3639	Approved
0.7216	Intermediate Similarity	NPD3640	Phase 3
0.7213	Intermediate Similarity	NPD3984	Clinical (unspecified phase)
0.7213	Intermediate Similarity	NPD7802	Discontinued
0.7213	Intermediate Similarity	NPD3983	Phase 3
0.7211	Intermediate Similarity	NPD8053	Approved
0.7211	Intermediate Similarity	NPD8054	Approved
0.7204	Intermediate Similarity	NPD4498	Clinical (unspecified phase)
0.7194	Intermediate Similarity	NPD7238	Clinical (unspecified phase)
0.7189	Intermediate Similarity	NPD2898	Approved
0.7188	Intermediate Similarity	NPD3349	Phase 2
0.7182	Intermediate Similarity	NPD4581	Clinical (unspecified phase)
0.7178	Intermediate Similarity	NPD5658	Approved
0.7166	Intermediate Similarity	NPD5810	Discontinued
0.7151	Intermediate Similarity	NPD4773	Phase 2
0.7151	Intermediate Similarity	NPD5966	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD4772	Phase 2
0.715	Intermediate Similarity	NPD5896	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD3110	Approved
0.7143	Intermediate Similarity	NPD3109	Approved
0.7135	Intermediate Similarity	NPD6357	Discontinued
0.7128	Intermediate Similarity	NPD5900	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD5241	Discontinued
0.7126	Intermediate Similarity	NPD5718	Phase 2
0.7119	Intermediate Similarity	NPD4727	Phase 1
0.7104	Intermediate Similarity	NPD7400	Phase 3
0.7098	Intermediate Similarity	NPD7906	Approved
0.709	Intermediate Similarity	NPD6496	Clinical (unspecified phase)
0.7085	Intermediate Similarity	NPD6612	Phase 2
0.7083	Intermediate Similarity	NPD4474	Approved
0.7083	Intermediate Similarity	NPD4475	Approved
0.7083	Intermediate Similarity	NPD6723	Discontinued
0.7074	Intermediate Similarity	NPD5521	Clinical (unspecified phase)
0.7072	Intermediate Similarity	NPD6818	Clinical (unspecified phase)
0.7071	Intermediate Similarity	NPD4420	Approved
0.7071	Intermediate Similarity	NPD6877	Discontinued
0.7071	Intermediate Similarity	NPD5071	Phase 2
0.7068	Intermediate Similarity	NPD2968	Approved
0.7068	Intermediate Similarity	NPD2971	Approved
0.7066	Intermediate Similarity	NPD2669	Clinical (unspecified phase)
0.7062	Intermediate Similarity	NPD3408	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD6046	Clinical (unspecified phase)
0.7033	Intermediate Similarity	NPD6063	Approved
0.7033	Intermediate Similarity	NPD2358	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD6107	Approved
0.7027	Intermediate Similarity	NPD4986	Clinical (unspecified phase)
0.7026	Intermediate Similarity	NPD5641	Discontinued
0.702	Intermediate Similarity	NPD7034	Discontinued
0.7015	Intermediate Similarity	NPD5006	Approved
0.7015	Intermediate Similarity	NPD5005	Approved
0.7011	Intermediate Similarity	NPD4796	Discontinued
0.6995	Remote Similarity	NPD1742	Approved
0.6995	Remote Similarity	NPD5530	Phase 1
0.6995	Remote Similarity	NPD1743	Approved
0.6995	Remote Similarity	NPD19	Approved
0.6989	Remote Similarity	NPD3845	Phase 1
0.6989	Remote Similarity	NPD4010	Discontinued
0.6989	Remote Similarity	NPD6071	Discontinued
0.6982	Remote Similarity	NPD554	Clinical (unspecified phase)
0.6979	Remote Similarity	NPD7280	Phase 3
0.6979	Remote Similarity	NPD7313	Approved
0.6979	Remote Similarity	NPD4577	Approved
0.6979	Remote Similarity	NPD7312	Approved
0.6979	Remote Similarity	NPD7310	Approved
0.6979	Remote Similarity	NPD7311	Approved
0.6979	Remote Similarity	NPD4578	Approved
0.6979	Remote Similarity	NPD7281	Phase 3
0.6971	Remote Similarity	NPD5754	Discontinued
0.6967	Remote Similarity	NPD7858	Clinical (unspecified phase)
0.6963	Remote Similarity	NPD7149	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD4885	Approved
0.6959	Remote Similarity	NPD4663	Approved
0.6957	Remote Similarity	NPD6533	Clinical (unspecified phase)
0.6949	Remote Similarity	NPD7598	Phase 2
0.6944	Remote Similarity	NPD7261	Clinical (unspecified phase)
0.6943	Remote Similarity	NPD7309	Approved
0.694	Remote Similarity	NPD2563	Approved
0.694	Remote Similarity	NPD2560	Approved
0.6938	Remote Similarity	NPD8149	Discontinued
0.6935	Remote Similarity	NPD6621	Clinical (unspecified phase)
0.6931	Remote Similarity	NPD3515	Approved
0.6931	Remote Similarity	NPD3516	Approved
0.6927	Remote Similarity	NPD8453	Clinical (unspecified phase)
0.6927	Remote Similarity	NPD6625	Approved
0.6923	Remote Similarity	NPD3398	Discontinued
0.6923	Remote Similarity	NPD1769	Discontinued
0.6923	Remote Similarity	NPD6812	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD7571	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD7945	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD6895	Approved
0.6919	Remote Similarity	NPD6896	Approved
0.6911	Remote Similarity	NPD6996	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD5752	Clinical (unspecified phase)
0.6898	Remote Similarity	NPD4166	Phase 2
0.6889	Remote Similarity	NPD814	Clinical (unspecified phase)
0.6884	Remote Similarity	NPD7667	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD6748	Discontinued
0.6875	Remote Similarity	NPD7225	Discontinued
0.6869	Remote Similarity	NPD6526	Approved
0.6869	Remote Similarity	NPD7278	Phase 2
0.6869	Remote Similarity	NPD7279	Phase 2
0.686	Remote Similarity	NPD2492	Phase 1
0.6856	Remote Similarity	NPD6021	Clinical (unspecified phase)
0.6854	Remote Similarity	NPD3124	Discontinued
0.6853	Remote Similarity	NPD2488	Approved
0.6853	Remote Similarity	NPD2490	Approved
0.685	Remote Similarity	NPD6284	Clinical (unspecified phase)
0.6848	Remote Similarity	NPD5978	Approved
0.6848	Remote Similarity	NPD5977	Approved
0.6845	Remote Similarity	NPD6457	Approved
0.6834	Remote Similarity	NPD4418	Discontinued
0.6832	Remote Similarity	NPD7255	Clinical (unspecified phase)
0.6823	Remote Similarity	NPD6297	Approved
0.6821	Remote Similarity	NPD5087	Clinical (unspecified phase)
0.6821	Remote Similarity	NPD6339	Approved
0.6821	Remote Similarity	NPD6340	Approved
0.6816	Remote Similarity	NPD1424	Approved
0.6813	Remote Similarity	NPD5617	Suspended
0.6809	Remote Similarity	NPD5847	Phase 1
0.6809	Remote Similarity	NPD6747	Phase 1
0.6808	Remote Similarity	NPD5070	Clinical (unspecified phase)
0.6806	Remote Similarity	NPD7223	Discontinued
0.6806	Remote Similarity	NPD5313	Approved
0.6806	Remote Similarity	NPD7224	Discontinued
0.6806	Remote Similarity	NPD5312	Approved
0.6804	Remote Similarity	NPD3534	Clinical (unspecified phase)
0.6798	Remote Similarity	NPD2422	Clinical (unspecified phase)
0.6796	Remote Similarity	NPD7222	Phase 2
0.6793	Remote Similarity	NPD2977	Approved
0.6793	Remote Similarity	NPD2978	Approved
0.6793	Remote Similarity	NPD6737	Phase 2
0.6793	Remote Similarity	NPD6738	Phase 2
0.6782	Remote Similarity	NPD3837	Clinical (unspecified phase)
0.6782	Remote Similarity	NPD4108	Discontinued
0.6782	Remote Similarity	NPD8095	Phase 1
0.6779	Remote Similarity	NPD4997	Clinical (unspecified phase)
0.6778	Remote Similarity	NPD3647	Clinical (unspecified phase)
0.6778	Remote Similarity	NPD6090	Discontinued
0.6774	Remote Similarity	NPD5604	Discontinued
0.6773	Remote Similarity	NPD6494	Phase 2
0.6773	Remote Similarity	NPD7922	Phase 1
0.6772	Remote Similarity	NPD6687	Approved
0.6772	Remote Similarity	NPD3975	Discontinued
0.6772	Remote Similarity	NPD6688	Approved
0.6766	Remote Similarity	NPD6527	Approved
0.6766	Remote Similarity	NPD2975	Approved
0.6766	Remote Similarity	NPD2974	Approved
0.6766	Remote Similarity	NPD2973	Approved
0.6765	Remote Similarity	NPD956	Clinical (unspecified phase)

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