NPASS Compound

Structure

CID67978 OpenBabel06191715402D 27 30 0 0 0 0 0 0 0 0999 V2000 -5.7608 -2.9271 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.7444 0.0046 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.3376 -0.9090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5797 1.4135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.5743 1.5181 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2709 -2.1180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2219 -2.4271 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2219 0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8171 -1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8171 0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7608 -1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5878 -0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1730 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6831 -1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6831 -0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7608 -0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2709 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.1620 0.7091 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9511 -1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9511 -0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7553 -0.2045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1730 -2.1180 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -2.6831 1.3090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.1566 0.8136 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.3431 -1.0135 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.6180 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 22 1 0 0 0 0 2 24 1 0 0 0 0 3 25 1 0 0 0 0 4 5 2 0 0 0 0 4 13 1 0 0 0 0 5 18 1 0 0 0 0 6 7 1 0 0 0 0 6 14 1 0 0 0 0 7 22 1 0 0 0 0 8 13 1 0 0 0 0 8 17 1 0 0 0 0 9 14 2 0 0 0 0 9 19 1 0 0 0 0 10 15 2 0 0 0 0 10 20 1 0 0 0 0 11 16 1 0 0 0 0 11 22 1 0 0 0 0 12 26 1 0 0 0 0 12 27 1 0 0 0 0 13 16 2 0 0 0 0 14 15 1 0 0 0 0 15 17 1 0 0 0 0 16 21 1 0 0 0 0 17 23 2 0 0 0 0 18 21 2 0 0 0 0 18 24 1 0 0 0 0 19 20 2 0 0 0 0 19 26 1 0 0 0 0 20 27 1 0 0 0 0 21 25 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	369.16
Volume:	374.039
LogP:	2.911
LogD:	2.832
LogS:	-4.098
# Rotatable Bonds:	2
TPSA:	57.23
# H-Bond Aceptor:	6
# H-Bond Donor:	0
# Rings:	4
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.811
Synthetic Accessibility Score:	3.017
Fsp3:	0.381
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:	-4.923
MDCK Permeability:	2.545790994190611e-05
Pgp-inhibitor:	0.027
Pgp-substrate:	0.169
Human Intestinal Absorption (HIA):	0.002
20% Bioavailability (F20%):	0.004
30% Bioavailability (F30%):	0.004

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.994
Plasma Protein Binding (PPB):	84.6672592163086%
Volume Distribution (VD):	1.977
Pgp-substrate:	8.697830200195312%

ADMET: Metabolism

CYP1A2-inhibitor:	0.821
CYP1A2-substrate:	0.939
CYP2C19-inhibitor:	0.632
CYP2C19-substrate:	0.934
CYP2C9-inhibitor:	0.036
CYP2C9-substrate:	0.816
CYP2D6-inhibitor:	0.96
CYP2D6-substrate:	0.919
CYP3A4-inhibitor:	0.939
CYP3A4-substrate:	0.913

ADMET: Excretion

Clearance (CL):	14.498
Half-life (T1/2):	0.4

ADMET: Toxicity

hERG Blockers:	0.648
Human Hepatotoxicity (H-HT):	0.565
Drug-inuced Liver Injury (DILI):	0.898
AMES Toxicity:	0.083
Rat Oral Acute Toxicity:	0.542
Maximum Recommended Daily Dose:	0.214
Skin Sensitization:	0.183
Carcinogencity:	0.669
Eye Corrosion:	0.003
Eye Irritation:	0.008
Respiratory Toxicity:	0.942

Download Data

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

Natural Product: NPC67978

Natural Product ID:	NPC67978
*Common Name:**	Allocryptopine
IUPAC Name:	n.a.
Synonyms:	Allocryptopine; Allocrytopine
Standard InCHIKey:	HYBRYAPKQCZIAE-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C21H23NO5/c1-22-7-6-14-9-19-20(27-12-26-19)10-15(14)17(23)8-13-4-5-18(24-2)21(25-3)16(13)11-22/h4-5,9-10H,6-8,11-12H2,1-3H3
SMILES:	CN1CCc2cc3c(cc2C(=O)Cc2ccc(c(c2C1)OC)OC)OCO3
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL520043
PubChem CID:	98570
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids and derivatives [CHEMONTID:0002743] Protopine 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
NPO24758	Angelica dahurica	Species	Apiaceae	Eukaryota	n.a.	root	n.a.	DOI[10.5012/bkcs.2003.24.11.1699]
NPO24024	Fusarium semitectum	Species	Nectriaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10978211]
NPO26193	Piper methysticum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11830162]
NPO29080	Ulex airensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11858751]
NPO20958	Smenospongia aurea	Species	Thorectidae	Eukaryota	n.a.	Jamaican	n.a.	PMID[11975483]
NPO24758	Angelica dahurica	Species	Apiaceae	Eukaryota	n.a.	root	n.a.	PMID[12510838]
NPO26193	Piper methysticum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12809361]
NPO21424	Garcinia xanthochymus	Species	Clusiaceae	Eukaryota	n.a.	xylem	n.a.	PMID[14600386]
NPO20254	Ipomoea leptophylla	Species	Convolvulaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[14640518]
NPO22556	Dendrolobium lanceolatum	Species	Fabaceae	Eukaryota	n.a.	root	n.a.	PMID[15217275]
NPO24758	Angelica dahurica	Species	Apiaceae	Eukaryota	n.a.	root	n.a.	PMID[15646793]
NPO21424	Garcinia xanthochymus	Species	Clusiaceae	Eukaryota	fruits	n.a.	n.a.	PMID[15787435]
NPO25373	Stereocaulon alpinum	Species	Stereocaulaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18288807]
NPO21435	Thalictrum faberi	Species	Ranunculaceae	Eukaryota	Roots	n.a.	n.a.	PMID[19299148]
NPO21782	Nuxia sphaerocephala	Species	Stilbaceae	Eukaryota	leaves	n.a.	n.a.	PMID[19299148]
NPO927	Swertia mussotii	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19645233]
NPO25345	Corydalis ternata	Species	Papaveraceae	Eukaryota	tubers	n.a.	n.a.	PMID[20594848]
NPO3504	Argemone mexicana	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21094631]
NPO24758	Angelica dahurica	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21625478]
NPO24758	Angelica dahurica	Species	Apiaceae	Eukaryota	n.a.	root	n.a.	PMID[21657081]
NPO24024	Fusarium semitectum	Species	Nectriaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22439674]
NPO827	Corydalis yanhusuo	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22737858]
NPO827	Corydalis yanhusuo	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23194502]
NPO26428	Ligularia sagitta	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24913558]
NPO13962	Corydalis turtschaninovii	Species	Papaveraceae	Eukaryota	n.a.	rhizome	n.a.	PMID[25277281]
NPO26193	Piper methysticum	Species	Piperaceae	Eukaryota	root	n.a.	n.a.	PMID[25597012]
NPO13962	Corydalis turtschaninovii	Species	Papaveraceae	Eukaryota	n.a.	tuber	n.a.	PMID[25670016]
NPO18823	Colysis pothifolia	Species	Polypodiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26731047]
NPO24758	Angelica dahurica	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27444348]
NPO25373	Stereocaulon alpinum	Species	Stereocaulaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[29878768]
NPO22441	Senna spectabilis	Species	Fabaceae	Eukaryota	flowers	n.a.	n.a.	PMID[30413343]
NPO24758	Angelica dahurica	Species	Apiaceae	Eukaryota	Roots	n.a.	n.a.	PMID[31464439]
NPO14045	Corydalis decumbens	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31599578]
NPO827	Corydalis yanhusuo	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32058719]
NPO41079	Toddalia asiatica	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[33001647]
NPO21435	Thalictrum faberi	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7528786]
NPO25657	Mezzettia leptopoda	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9868159]
NPO927	Swertia mussotii	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[Article]
NPO29249	Prunus humilis	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO2114.1	Thalictrum minus var. hypoleucum	Varieties	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO827	Corydalis yanhusuo	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO13297	Thalictrum atriplex	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO927	Swertia mussotii	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO22043	Hylomecon japonica	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO14045	Corydalis decumbens	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO16640	Thalictrum petaloideum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28698	Corydalis remota	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO21004	Nicotiana plumbaginifolia	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO6027.1	Corydalis ambigua var. amurensis	Varieties	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO1106	Artabotrys maingayi	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO21451	Thalictrum simplex	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO29514	Stizolobium capitatum	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[HerDing]
NPO20871	Pueraria tuberosa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO13637	Thalictrum foliolosum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO24758	Angelica dahurica	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO16414	Thuja plicata	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO21435	Thalictrum faberi	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO3504	Argemone mexicana	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO20090	Dalbergia spruceana	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26193	Piper methysticum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26428	Ligularia sagitta	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO13887	Erythrophleum suaveolens	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15847	Thalictrum glandulosissimum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO24480	Diospyros ebenum	Species	Ebenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO19264	Macleaya cordata	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO21782	Nuxia sphaerocephala	Species	Stilbaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO30288	Thalictrum thunbergii	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO23223	Symphytum officinale	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO25761	Thalictrum microgynum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11457	Chelidonium majus	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO21424	Garcinia xanthochymus	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO21004	Nicotiana plumbaginifolia	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25761	Thalictrum microgynum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13887	Erythrophleum suaveolens	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25373	Stereocaulon alpinum	Species	Stereocaulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6027.1	Corydalis ambigua var. amurensis	Varieties	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21782	Nuxia sphaerocephala	Species	Stilbaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22043	Hylomecon japonica	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO29249	Prunus humilis	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO927	Swertia mussotii	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3504	Argemone mexicana	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26230	Lappula echinata	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23223	Symphytum officinale	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24087	Psacalium peltatum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21424	Garcinia xanthochymus	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19361	Herba meconpsis integrifoliae	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[TCMID]
NPO2114.1	Thalictrum minus var. hypoleucum	Varieties	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19264	Macleaya cordata	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO827	Corydalis yanhusuo	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26193	Piper methysticum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24758	Angelica dahurica	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14045	Corydalis decumbens	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24480	Diospyros ebenum	Species	Ebenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11457	Chelidonium majus	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25166	Corydalis ophiocarpa	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO29514	Stizolobium capitatum	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[TCMID]
NPO16640	Thalictrum petaloideum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28698	Corydalis remota	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15847	Thalictrum glandulosissimum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20090	Dalbergia spruceana	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26428	Ligularia sagitta	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21435	Thalictrum faberi	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16414	Thuja plicata	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13637	Thalictrum foliolosum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13297	Thalictrum atriplex	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20871	Pueraria tuberosa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21451	Thalictrum simplex	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1106	Artabotrys maingayi	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO827	Corydalis yanhusuo	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO24480	Diospyros ebenum	Species	Ebenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO20090	Dalbergia spruceana	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO28698	Corydalis remota	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO3504	Argemone mexicana	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO26193	Piper methysticum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO23223	Symphytum officinale	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO24758	Angelica dahurica	Species	Apiaceae	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]
NPO13637	Thalictrum foliolosum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO22043	Hylomecon japonica	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO25166	Corydalis ophiocarpa	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO30288	Thalictrum thunbergii	Species	Ranunculaceae	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]
NPO14045	Corydalis decumbens	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO13887	Erythrophleum suaveolens	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO827	Corydalis yanhusuo	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO24758	Angelica dahurica	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO13962	Corydalis turtschaninovii	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO29249	Prunus humilis	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO25345	Corydalis ternata	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO14045	Corydalis decumbens	Species	Papaveraceae	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]
NPO25761	Thalictrum microgynum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21848	Rosa hybr	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24868	Streptomyces aizunensis	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO28873	Epinetrum mangenotii	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO21677	Liatris aspera	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17383	Cyperus nipponicus	Species	Cyperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28698	Corydalis remota	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17360	Argemone albiflora	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25657	Mezzettia leptopoda	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26230	Lappula echinata	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19264	Macleaya cordata	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13962	Corydalis turtschaninovii	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25166	Corydalis ophiocarpa	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21424	Garcinia xanthochymus	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25345	Corydalis ternata	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8315	Wunderlichia crulsiana	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22043	Hylomecon japonica	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18613	Commiphora erlangeriana	Species	Burseraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21143	Cryptocarya canelilla	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22556	Dendrolobium lanceolatum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO336	Chaetomorpha moniligera	Species	Cladophoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29272	Paronychia argentea	Species	Caryophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22441	Senna spectabilis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29249	Prunus humilis	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20254	Ipomoea leptophylla	Species	Convolvulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23007	Horsfieldia glabra	Species	Myristicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO927	Swertia mussotii	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19966	Dendrobium amplum	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25624	Teclea sudanica	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3504	Argemone mexicana	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21026	Pericopsis mooniana	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13887	Erythrophleum suaveolens	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8144	Labidiaster annulatus	Species	Labidiasteridae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18823	Colysis pothifolia	Species	Polypodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23296	Teucrium carolipaui	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15221	Crambe fruticosa	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20871	Pueraria tuberosa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21782	Nuxia sphaerocephala	Species	Stilbaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO827	Corydalis yanhusuo	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO260	Cyclacanthia bellae	Species	Latrunculiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29080	Ulex airensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25484	Bumelia obtusifolia	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO21451	Thalictrum simplex	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24024	Fusarium semitectum	Species	Nectriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20090	Dalbergia spruceana	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25373	Stereocaulon alpinum	Species	Stereocaulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24758	Angelica dahurica	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20958	Smenospongia aurea	Species	Thorectidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28458	Coccoloba dugandiana	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25505	Astilbe japonica	Species	Saxifragaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29053	Dictyostelium longosporum	Species	n.a.	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14326	Pseudocercospora fijiensis	Species	Mycosphaerellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29520	Curculigo breviscapa	Species	Hypoxidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2114.1	Thalictrum minus var. hypoleucum	Varieties	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25881	Stachys plumosa	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19340	Orobanche caerulescens	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13637	Thalictrum foliolosum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18680	Larix decidua	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22495	Cladonia alpestris	Species	Cladoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29514	Stizolobium capitatum	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO26193	Piper methysticum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24480	Diospyros ebenum	Species	Ebenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26428	Ligularia sagitta	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21004	Nicotiana plumbaginifolia	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21230	Heterodermia obscurata	Species	Physciaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14045	Corydalis decumbens	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1106	Artabotrys maingayi	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24087	Psacalium peltatum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4790	Bocconia cordata	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25619	Vitex divaricata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18257	Oberna wallichiana	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO29235	Musca autumnalis	Species	Muscidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16414	Thuja plicata	Species	Cupressaceae	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]
NPO7177	Inocybe rimosa	Species	Inocybaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13216	Streptomyces pulveraceus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO18580	Diabelia spathulata	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20271	Canarina canariensis	Species	Campanulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25316	Lasius niger	Species	Formicidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22817	Actinidia valvata	Species	Actinidiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23223	Symphytum officinale	Species	Boraginaceae	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	4
Ki	1
Potency	6

Activity Type	# Activity
Cell Line	1
Individual Protein	5
Organism	4
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	IC50	>	338000.0	nM	PMID[464274]
NPT1038	Individual Protein	Histone-lysine N-methyltransferase MLL	Homo sapiens	Potency	=	14125.4	nM	PMID[464275]
NPT160	Individual Protein	TAR DNA-binding protein 43	Homo sapiens	Potency	n.a.	35481.3	nM	PMID[464275]
NPT49	Individual Protein	DNA-(apurinic or apyrimidinic site) lyase	Homo sapiens	Potency	n.a.	3162.3	nM	PMID[464275]
NPT110	Individual Protein	Cytochrome P450 2D6	Homo sapiens	Ki	=	122.0	nM	PMID[464277]
NPT485	Organism	Plasmodium falciparum (isolate K1 / Thailand)	Plasmodium falciparum K1	IC50	=	5080.0	nM	PMID[464274]
NPT992	Organism	Entamoeba histolytica	Entamoeba histolytica	IC50	=	135000.0	nM	PMID[464274]
NPT8	Individual Protein	DNA polymerase iota	Homo sapiens	Potency	n.a.	100000.0	nM	PMID[464275]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	Potency	n.a.	11689.1	nM	PMID[464275]
NPT2	Others	Unspecified		Potency	n.a.	6309.6	nM	PMID[464275]
NPT992	Organism	Entamoeba histolytica	Entamoeba histolytica	IC50	=	49.81	ug.mL-1	PMID[464276]

☑ 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 NPC67978 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	308
0.1-0.2	1645
0.2-0.3	5552
0.3-0.4	11978
0.4-0.5	4320
0.5-0.6	10360
0.6-0.7	7738
0.7-0.8	718
0.8-0.85	62
0.85-0.9	10
0.9-0.95	1
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC303581
0.9874	High Similarity	NPC308267
0.963	High Similarity	NPC121400
0.9623	High Similarity	NPC86469
0.9554	High Similarity	NPC153631
0.8765	High Similarity	NPC27887
0.8621	High Similarity	NPC477259
0.8621	High Similarity	NPC169387
0.8506	High Similarity	NPC116007
0.8447	Intermediate Similarity	NPC470088
0.8398	Intermediate Similarity	NPC207239
0.8371	Intermediate Similarity	NPC226708
0.8354	Intermediate Similarity	NPC470708
0.8344	Intermediate Similarity	NPC119669
0.8333	Intermediate Similarity	NPC477258
0.8313	Intermediate Similarity	NPC469978
0.8295	Intermediate Similarity	NPC83511
0.8287	Intermediate Similarity	NPC24228
0.8266	Intermediate Similarity	NPC207721
0.8249	Intermediate Similarity	NPC18306
0.8218	Intermediate Similarity	NPC222524
0.8193	Intermediate Similarity	NPC41178
0.8193	Intermediate Similarity	NPC216459
0.8193	Intermediate Similarity	NPC138487
0.8177	Intermediate Similarity	NPC469816
0.8177	Intermediate Similarity	NPC469815
0.8167	Intermediate Similarity	NPC63152
0.816	Intermediate Similarity	NPC475959
0.8144	Intermediate Similarity	NPC146288
0.8142	Intermediate Similarity	NPC215098
0.8142	Intermediate Similarity	NPC70290
0.8142	Intermediate Similarity	NPC71124
0.8142	Intermediate Similarity	NPC14622
0.8142	Intermediate Similarity	NPC46744
0.8142	Intermediate Similarity	NPC73020
0.8142	Intermediate Similarity	NPC124302
0.8084	Intermediate Similarity	NPC93593
0.8075	Intermediate Similarity	NPC268077
0.8065	Intermediate Similarity	NPC2173
0.8065	Intermediate Similarity	NPC328700
0.8065	Intermediate Similarity	NPC119818
0.8065	Intermediate Similarity	NPC202771
0.8054	Intermediate Similarity	NPC120671
0.8054	Intermediate Similarity	NPC314100
0.8054	Intermediate Similarity	NPC72788
0.8054	Intermediate Similarity	NPC226652
0.8047	Intermediate Similarity	NPC106786
0.8046	Intermediate Similarity	NPC227683
0.8036	Intermediate Similarity	NPC234392
0.8036	Intermediate Similarity	NPC31311
0.8033	Intermediate Similarity	NPC125924
0.8025	Intermediate Similarity	NPC86455
0.8025	Intermediate Similarity	NPC125134
0.8025	Intermediate Similarity	NPC137920
0.8022	Intermediate Similarity	NPC254957
0.8021	Intermediate Similarity	NPC207971
0.8012	Intermediate Similarity	NPC59567
0.8	Intermediate Similarity	NPC5374
0.8	Intermediate Similarity	NPC135006
0.7977	Intermediate Similarity	NPC284842
0.7956	Intermediate Similarity	NPC141440
0.7952	Intermediate Similarity	NPC223125
0.7925	Intermediate Similarity	NPC7018
0.791	Intermediate Similarity	NPC35680
0.7861	Intermediate Similarity	NPC276944
0.7861	Intermediate Similarity	NPC238530
0.7861	Intermediate Similarity	NPC306669
0.7861	Intermediate Similarity	NPC231198
0.7861	Intermediate Similarity	NPC232514
0.7857	Intermediate Similarity	NPC210148
0.7857	Intermediate Similarity	NPC166979
0.7857	Intermediate Similarity	NPC223124
0.7857	Intermediate Similarity	NPC58661
0.7857	Intermediate Similarity	NPC208890
0.7857	Intermediate Similarity	NPC233029
0.7849	Intermediate Similarity	NPC23080
0.7849	Intermediate Similarity	NPC193906
0.7838	Intermediate Similarity	NPC33256
0.7818	Intermediate Similarity	NPC229787
0.7809	Intermediate Similarity	NPC5167
0.7809	Intermediate Similarity	NPC85613
0.7803	Intermediate Similarity	NPC476569
0.7802	Intermediate Similarity	NPC474009
0.7791	Intermediate Similarity	NPC28398
0.7791	Intermediate Similarity	NPC160298
0.7791	Intermediate Similarity	NPC477559
0.7791	Intermediate Similarity	NPC266753
0.7791	Intermediate Similarity	NPC232924
0.7791	Intermediate Similarity	NPC306902
0.7771	Intermediate Similarity	NPC476144
0.7771	Intermediate Similarity	NPC16107
0.7771	Intermediate Similarity	NPC51957
0.7771	Intermediate Similarity	NPC210437
0.7771	Intermediate Similarity	NPC106295
0.7758	Intermediate Similarity	NPC145304
0.7758	Intermediate Similarity	NPC46880
0.7751	Intermediate Similarity	NPC148898
0.773	Intermediate Similarity	NPC213206
0.773	Intermediate Similarity	NPC474915
0.773	Intermediate Similarity	NPC188163
0.773	Intermediate Similarity	NPC328750
0.7727	Intermediate Similarity	NPC241055
0.7725	Intermediate Similarity	NPC59907
0.7725	Intermediate Similarity	NPC37144
0.7725	Intermediate Similarity	NPC7467
0.7722	Intermediate Similarity	NPC149285
0.7714	Intermediate Similarity	NPC24264
0.7714	Intermediate Similarity	NPC476432
0.7706	Intermediate Similarity	NPC220577
0.7704	Intermediate Similarity	NPC55470
0.7697	Intermediate Similarity	NPC4669
0.7692	Intermediate Similarity	NPC476579
0.7683	Intermediate Similarity	NPC138438
0.7683	Intermediate Similarity	NPC908
0.7679	Intermediate Similarity	NPC469540
0.7679	Intermediate Similarity	NPC211296
0.7679	Intermediate Similarity	NPC469539
0.767	Intermediate Similarity	NPC247389
0.7669	Intermediate Similarity	NPC314682
0.7665	Intermediate Similarity	NPC476151
0.7661	Intermediate Similarity	NPC78733
0.7657	Intermediate Similarity	NPC16805
0.7657	Intermediate Similarity	NPC225774
0.7657	Intermediate Similarity	NPC167546
0.7657	Intermediate Similarity	NPC302527
0.7643	Intermediate Similarity	NPC172403
0.7643	Intermediate Similarity	NPC286683
0.7637	Intermediate Similarity	NPC102760
0.763	Intermediate Similarity	NPC118804
0.763	Intermediate Similarity	NPC111485
0.7629	Intermediate Similarity	NPC46990
0.7624	Intermediate Similarity	NPC99723
0.7614	Intermediate Similarity	NPC219341
0.7609	Intermediate Similarity	NPC471650
0.7609	Intermediate Similarity	NPC162694
0.7605	Intermediate Similarity	NPC290404
0.7602	Intermediate Similarity	NPC118332
0.7598	Intermediate Similarity	NPC2314
0.7593	Intermediate Similarity	NPC95485
0.7593	Intermediate Similarity	NPC89504
0.7593	Intermediate Similarity	NPC88065
0.7588	Intermediate Similarity	NPC37220
0.7584	Intermediate Similarity	NPC474708
0.7574	Intermediate Similarity	NPC477565
0.7574	Intermediate Similarity	NPC103379
0.7571	Intermediate Similarity	NPC210918
0.7571	Intermediate Similarity	NPC298979
0.7565	Intermediate Similarity	NPC80472
0.756	Intermediate Similarity	NPC296575
0.756	Intermediate Similarity	NPC224687
0.7558	Intermediate Similarity	NPC169742
0.7557	Intermediate Similarity	NPC168409
0.7553	Intermediate Similarity	NPC470646
0.7547	Intermediate Similarity	NPC160193
0.7546	Intermediate Similarity	NPC252107
0.7546	Intermediate Similarity	NPC225745
0.754	Intermediate Similarity	NPC94499
0.753	Intermediate Similarity	NPC476567
0.753	Intermediate Similarity	NPC136860
0.753	Intermediate Similarity	NPC128019
0.7529	Intermediate Similarity	NPC478189
0.7529	Intermediate Similarity	NPC477080
0.7528	Intermediate Similarity	NPC475845
0.7516	Intermediate Similarity	NPC266425
0.7515	Intermediate Similarity	NPC153620
0.7515	Intermediate Similarity	NPC223336
0.7515	Intermediate Similarity	NPC24257
0.7514	Intermediate Similarity	NPC86144
0.7514	Intermediate Similarity	NPC304659
0.7514	Intermediate Similarity	NPC57512
0.75	Intermediate Similarity	NPC327052
0.75	Intermediate Similarity	NPC104353
0.7486	Intermediate Similarity	NPC75958
0.7485	Intermediate Similarity	NPC99078
0.7473	Intermediate Similarity	NPC294790
0.7473	Intermediate Similarity	NPC118633
0.7473	Intermediate Similarity	NPC148693
0.7472	Intermediate Similarity	NPC474324
0.7472	Intermediate Similarity	NPC57812
0.7459	Intermediate Similarity	NPC214629
0.7457	Intermediate Similarity	NPC39701
0.7457	Intermediate Similarity	NPC207757
0.7457	Intermediate Similarity	NPC184026
0.7457	Intermediate Similarity	NPC249797
0.7457	Intermediate Similarity	NPC5238
0.7457	Intermediate Similarity	NPC189266
0.7457	Intermediate Similarity	NPC469817
0.7457	Intermediate Similarity	NPC172765
0.7457	Intermediate Similarity	NPC127674
0.7457	Intermediate Similarity	NPC295691
0.7457	Intermediate Similarity	NPC2413
0.7457	Intermediate Similarity	NPC204828
0.7457	Intermediate Similarity	NPC276588
0.7457	Intermediate Similarity	NPC54379
0.7457	Intermediate Similarity	NPC278799
0.7457	Intermediate Similarity	NPC76079
0.7457	Intermediate Similarity	NPC193949
0.7457	Intermediate Similarity	NPC110416
0.7455	Intermediate Similarity	NPC470962
0.7452	Intermediate Similarity	NPC30216

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 NPC67978 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	207
0.1-0.2	780
0.2-0.3	1001
0.3-0.4	2005
0.4-0.5	2609
0.5-0.6	1796
0.6-0.7	657
0.7-0.8	89
0.8-0.85	4
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8537	High Similarity	NPD5977	Approved
0.8537	High Similarity	NPD5978	Approved
0.8142	Intermediate Similarity	NPD4420	Approved
0.8065	Intermediate Similarity	NPD5005	Approved
0.8065	Intermediate Similarity	NPD5006	Approved
0.7917	Intermediate Similarity	NPD6385	Approved
0.7917	Intermediate Similarity	NPD6386	Approved
0.7805	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.7798	Intermediate Similarity	NPD824	Approved
0.7784	Intermediate Similarity	NPD6662	Clinical (unspecified phase)
0.7784	Intermediate Similarity	NPD3640	Phase 3
0.7784	Intermediate Similarity	NPD3639	Approved
0.7784	Intermediate Similarity	NPD3641	Approved
0.7771	Intermediate Similarity	NPD4584	Approved
0.7771	Intermediate Similarity	NPD5242	Approved
0.7751	Intermediate Similarity	NPD1337	Clinical (unspecified phase)
0.773	Intermediate Similarity	NPD4664	Clinical (unspecified phase)
0.7706	Intermediate Similarity	NPD6873	Phase 2
0.768	Intermediate Similarity	NPD7280	Phase 3
0.768	Intermediate Similarity	NPD7281	Phase 3
0.7647	Intermediate Similarity	NPD6875	Approved
0.7647	Intermediate Similarity	NPD6876	Approved
0.7637	Intermediate Similarity	NPD6618	Phase 2
0.7622	Intermediate Similarity	NPD5525	Clinical (unspecified phase)
0.7606	Intermediate Similarity	NPD5564	Approved
0.7602	Intermediate Similarity	NPD7110	Phase 1
0.7602	Intermediate Similarity	NPD7109	Clinical (unspecified phase)
0.7579	Intermediate Similarity	NPD5457	Discontinued
0.7572	Intermediate Similarity	NPD5616	Clinical (unspecified phase)
0.7474	Intermediate Similarity	NPD7607	Clinical (unspecified phase)
0.7473	Intermediate Similarity	NPD7235	Clinical (unspecified phase)
0.7423	Intermediate Similarity	NPD2492	Phase 1
0.7398	Intermediate Similarity	NPD4859	Phase 1
0.7391	Intermediate Similarity	NPD3534	Clinical (unspecified phase)
0.7378	Intermediate Similarity	NPD743	Approved
0.7368	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD1670	Discontinued
0.7337	Intermediate Similarity	NPD6783	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD2898	Approved
0.7326	Intermediate Similarity	NPD7291	Discontinued
0.732	Intermediate Similarity	NPD956	Clinical (unspecified phase)
0.7316	Intermediate Similarity	NPD4413	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD5313	Approved
0.7308	Intermediate Similarity	NPD5312	Approved
0.7308	Intermediate Similarity	NPD3050	Clinical (unspecified phase)
0.7306	Intermediate Similarity	NPD4107	Approved
0.7306	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD2971	Approved
0.7297	Intermediate Similarity	NPD2968	Approved
0.7288	Intermediate Similarity	NPD8005	Clinical (unspecified phase)
0.7277	Intermediate Similarity	NPD7667	Clinical (unspecified phase)
0.7228	Intermediate Similarity	NPD6297	Approved
0.7196	Intermediate Similarity	NPD6377	Clinical (unspecified phase)
0.7195	Intermediate Similarity	NPD3142	Approved
0.7195	Intermediate Similarity	NPD3140	Approved
0.7184	Intermediate Similarity	NPD4017	Approved
0.7179	Intermediate Similarity	NPD4482	Phase 3
0.7175	Intermediate Similarity	NPD2560	Approved
0.7175	Intermediate Similarity	NPD2563	Approved
0.7169	Intermediate Similarity	NPD6895	Approved
0.7169	Intermediate Similarity	NPD6896	Approved
0.7168	Intermediate Similarity	NPD6030	Approved
0.7168	Intermediate Similarity	NPD6031	Approved
0.7167	Intermediate Similarity	NPD6107	Approved
0.7166	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7158	Intermediate Similarity	NPD3808	Clinical (unspecified phase)
0.7136	Intermediate Similarity	NPD5950	Discontinued
0.7126	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7123	Intermediate Similarity	NPD6625	Approved
0.7117	Intermediate Similarity	NPD2669	Clinical (unspecified phase)
0.7113	Intermediate Similarity	NPD5071	Phase 2
0.7112	Intermediate Similarity	NPD6146	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD1307	Phase 2
0.7095	Intermediate Similarity	NPD1309	Phase 2
0.7093	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.709	Intermediate Similarity	NPD4084	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD2651	Approved
0.7086	Intermediate Similarity	NPD2649	Approved
0.7083	Intermediate Similarity	NPD4466	Phase 1
0.7081	Intermediate Similarity	NPD5441	Clinical (unspecified phase)
0.7079	Intermediate Similarity	NPD5353	Approved
0.7074	Intermediate Similarity	NPD6853	Approved
0.7074	Intermediate Similarity	NPD6851	Approved
0.7073	Intermediate Similarity	NPD5718	Phase 2
0.7068	Intermediate Similarity	NPD2490	Approved
0.7068	Intermediate Similarity	NPD2488	Approved
0.7065	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7062	Intermediate Similarity	NPD6279	Approved
0.7062	Intermediate Similarity	NPD6280	Approved
0.7062	Intermediate Similarity	NPD2973	Approved
0.7062	Intermediate Similarity	NPD2974	Approved
0.7062	Intermediate Similarity	NPD2975	Approved
0.7062	Intermediate Similarity	NPD7298	Approved
0.7059	Intermediate Similarity	NPD2654	Approved
0.7056	Intermediate Similarity	NPD3057	Approved
0.7053	Intermediate Similarity	NPD6040	Clinical (unspecified phase)
0.7033	Intermediate Similarity	NPD4166	Phase 2
0.7033	Intermediate Similarity	NPD6747	Phase 1
0.7031	Intermediate Similarity	NPD7296	Approved
0.703	Intermediate Similarity	NPD554	Clinical (unspecified phase)
0.7011	Intermediate Similarity	NPD3647	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD3863	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD7833	Phase 2
0.7	Intermediate Similarity	NPD7831	Phase 2
0.7	Intermediate Similarity	NPD7832	Clinical (unspecified phase)
0.698	Remote Similarity	NPD5914	Approved
0.6973	Remote Similarity	NPD2822	Clinical (unspecified phase)
0.6973	Remote Similarity	NPD8252	Approved
0.6973	Remote Similarity	NPD8099	Discontinued
0.6973	Remote Similarity	NPD7177	Discontinued
0.6973	Remote Similarity	NPD8251	Approved
0.6971	Remote Similarity	NPD5586	Clinical (unspecified phase)
0.697	Remote Similarity	NPD3448	Approved
0.697	Remote Similarity	NPD3533	Approved
0.697	Remote Similarity	NPD2491	Approved
0.697	Remote Similarity	NPD2972	Approved
0.6968	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6968	Remote Similarity	NPD7190	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD7577	Discontinued
0.6966	Remote Similarity	NPD6844	Discontinued
0.6957	Remote Similarity	NPD4481	Phase 3
0.6957	Remote Similarity	NPD4575	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD6894	Phase 1
0.6954	Remote Similarity	NPD4580	Approved
0.6954	Remote Similarity	NPD7255	Clinical (unspecified phase)
0.6946	Remote Similarity	NPD683	Approved
0.6944	Remote Similarity	NPD4846	Phase 2
0.6944	Remote Similarity	NPD4947	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD5019	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD6788	Approved
0.694	Remote Similarity	NPD6808	Phase 2
0.694	Remote Similarity	NPD6071	Discontinued
0.6935	Remote Similarity	NPD8156	Discontinued
0.6919	Remote Similarity	NPD2494	Approved
0.6919	Remote Similarity	NPD3452	Approved
0.6919	Remote Similarity	NPD3450	Approved
0.6919	Remote Similarity	NPD2493	Approved
0.6915	Remote Similarity	NPD7039	Approved
0.6915	Remote Similarity	NPD7038	Approved
0.6915	Remote Similarity	NPD5192	Clinical (unspecified phase)
0.691	Remote Similarity	NPD4772	Phase 2
0.691	Remote Similarity	NPD4773	Phase 2
0.6907	Remote Similarity	NPD6181	Discontinued
0.6905	Remote Similarity	NPD7279	Phase 2
0.6905	Remote Similarity	NPD7278	Phase 2
0.6905	Remote Similarity	NPD5619	Clinical (unspecified phase)
0.6902	Remote Similarity	NPD8051	Clinical (unspecified phase)
0.6893	Remote Similarity	NPD7261	Clinical (unspecified phase)
0.6885	Remote Similarity	NPD2821	Approved
0.6885	Remote Similarity	NPD7802	Discontinued
0.6884	Remote Similarity	NPD7626	Approved
0.6884	Remote Similarity	NPD7627	Approved
0.6882	Remote Similarity	NPD4476	Approved
0.6882	Remote Similarity	NPD2163	Approved
0.6882	Remote Similarity	NPD3818	Discontinued
0.6882	Remote Similarity	NPD4477	Approved
0.6879	Remote Similarity	NPD5307	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD5241	Discontinued
0.6872	Remote Similarity	NPD7317	Phase 3
0.6872	Remote Similarity	NPD7248	Discontinued
0.6865	Remote Similarity	NPD3451	Clinical (unspecified phase)
0.6862	Remote Similarity	NPD3823	Discontinued
0.6857	Remote Similarity	NPD1424	Approved
0.6848	Remote Similarity	NPD5183	Approved
0.6848	Remote Similarity	NPD5186	Approved
0.6839	Remote Similarity	NPD7124	Phase 2
0.6836	Remote Similarity	NPD4210	Discontinued
0.6835	Remote Similarity	NPD5536	Phase 2
0.6833	Remote Similarity	NPD2978	Approved
0.6833	Remote Similarity	NPD2977	Approved
0.6833	Remote Similarity	NPD4585	Approved
0.6831	Remote Similarity	NPD5494	Approved
0.6831	Remote Similarity	NPD7201	Clinical (unspecified phase)
0.6828	Remote Similarity	NPD3446	Phase 1
0.6826	Remote Similarity	NPD4474	Approved
0.6826	Remote Similarity	NPD4475	Approved
0.6816	Remote Similarity	NPD4583	Approved
0.6816	Remote Similarity	NPD4582	Approved
0.681	Remote Similarity	NPD1876	Approved
0.6809	Remote Similarity	NPD3885	Approved
0.6805	Remote Similarity	NPD2653	Approved
0.6802	Remote Similarity	NPD3655	Clinical (unspecified phase)
0.6798	Remote Similarity	NPD7458	Discontinued
0.6796	Remote Similarity	NPD7318	Phase 3
0.679	Remote Similarity	NPD3972	Approved
0.6788	Remote Similarity	NPD3349	Phase 2
0.6788	Remote Similarity	NPD7693	Approved
0.6786	Remote Similarity	NPD3473	Clinical (unspecified phase)
0.678	Remote Similarity	NPD7427	Discontinued
0.678	Remote Similarity	NPD1914	Approved
0.678	Remote Similarity	NPD5976	Discontinued
0.678	Remote Similarity	NPD5676	Approved
0.6779	Remote Similarity	NPD5980	Discovery
0.6766	Remote Similarity	NPD4002	Approved
0.6766	Remote Similarity	NPD4004	Approved
0.6763	Remote Similarity	NPD4162	Approved
0.6762	Remote Similarity	NPD7858	Clinical (unspecified phase)
0.6761	Remote Similarity	NPD3688	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