NPASS Compound

Structure

CID49075 OpenBabel06191715382D 45 51 0 0 1 0 0 0 0 0999 V2000 2.3279 -4.1855 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3765 -0.7229 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3279 1.6779 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9520 1.6154 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7342 1.9392 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1507 -4.5426 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0113 -4.0807 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5524 -1.5430 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7377 -4.6187 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6790 -4.1398 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9061 -2.4360 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1742 -1.7424 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0210 0.8862 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1742 -2.7197 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6000 0.5056 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1535 -3.3299 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3649 -1.0452 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5861 -2.3940 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3279 -0.2766 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1019 0.9857 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6353 -1.2538 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6451 -3.8006 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5880 -1.7011 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3279 -1.2538 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4019 0.5750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3511 -3.9716 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4816 -1.7424 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4816 -2.7197 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.9408 -0.4972 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.3096 -3.1889 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3593 -3.0487 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4816 0.2121 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6353 -0.2766 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5962 0.9312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3618 -0.1167 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3906 0.4660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6907 0.0553 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3279 -3.2083 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -2.5599 -0.1861 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -3.6695 -4.0974 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4816 1.1893 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0196 1.7202 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.5810 0.3612 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.9322 -3.5943 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 38 1 0 0 0 0 2 39 1 0 0 0 0 3 41 1 0 0 0 0 4 42 1 0 0 0 0 5 43 1 0 0 0 0 6 9 1 0 0 0 0 6 22 2 0 0 0 0 7 10 2 0 0 0 0 7 22 1 0 0 0 0 8 11 2 0 0 0 0 8 23 1 0 0 0 0 9 26 2 0 0 0 0 10 26 1 0 0 0 0 11 30 1 0 0 0 0 12 14 1 0 0 0 0 12 24 1 0 0 0 0 13 15 1 0 0 0 0 13 25 1 0 0 0 0 14 38 1 0 0 0 0 15 39 1 0 0 0 0 16 22 1 0 0 0 0 17 23 1 0 0 0 0 18 23 2 0 0 0 0 18 31 1 0 0 0 0 19 24 2 0 0 0 0 19 32 1 0 0 0 0 20 25 2 0 0 0 0 20 34 1 0 0 0 0 21 27 2 0 0 0 0 21 33 1 0 0 0 0 24 27 1 0 0 0 0 25 35 1 0 0 0 0 26 44 1 0 0 0 0 27 28 1 0 0 0 0 28 16 1 1 0 0 0 28 38 1 0 0 0 0 29 17 1 1 0 0 0 29 35 1 0 0 0 0 29 39 1 0 0 0 0 30 31 2 0 0 0 0 30 40 1 0 0 0 0 31 44 1 0 0 0 0 32 33 2 0 0 0 0 32 41 1 0 0 0 0 33 45 1 0 0 0 0 34 36 2 0 0 0 0 34 42 1 0 0 0 0 35 37 2 0 0 0 0 36 37 1 0 0 0 0 36 43 1 0 0 0 0 37 45 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	608.29
Volume:	631.71
LogP:	6.029
LogD:	4.018
LogS:	-5.818
# Rotatable Bonds:	3
TPSA:	72.86
# H-Bond Aceptor:	8
# H-Bond Donor:	1
# Rings:	8
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.271
Synthetic Accessibility Score:	5.74
Fsp3:	0.351
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.759
MDCK Permeability:	2.4902399673010223e-05
Pgp-inhibitor:	0.999
Pgp-substrate:	0.917
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.342
30% Bioavailability (F30%):	0.961

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.215
Plasma Protein Binding (PPB):	74.7857437133789%
Volume Distribution (VD):	1.051
Pgp-substrate:	17.471391677856445%

ADMET: Metabolism

CYP1A2-inhibitor:	0.059
CYP1A2-substrate:	0.968
CYP2C19-inhibitor:	0.071
CYP2C19-substrate:	0.969
CYP2C9-inhibitor:	0.046
CYP2C9-substrate:	0.611
CYP2D6-inhibitor:	0.013
CYP2D6-substrate:	0.958
CYP3A4-inhibitor:	0.084
CYP3A4-substrate:	0.954

ADMET: Excretion

Clearance (CL):	9.98
Half-life (T1/2):	0.308

ADMET: Toxicity

hERG Blockers:	0.961
Human Hepatotoxicity (H-HT):	0.027
Drug-inuced Liver Injury (DILI):	0.386
AMES Toxicity:	0.121
Rat Oral Acute Toxicity:	0.377
Maximum Recommended Daily Dose:	0.994
Skin Sensitization:	0.803
Carcinogencity:	0.04
Eye Corrosion:	0.003
Eye Irritation:	0.005
Respiratory Toxicity:	0.441

Download Data

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

Natural Product: NPC49075

Natural Product ID:	NPC49075
*Common Name:**	Berbamine
IUPAC Name:	n.a.
Synonyms:	NSC-369310
Standard InCHIKey:	DFOCUWZXJBAUSQ-URLMMPGGSA-N
Standard InCHI:	InChI=1S/C37H40N2O6/c1-38-14-12-24-19-32(41-3)33-21-27(24)28(38)16-22-6-9-26(10-7-22)44-31-18-23(8-11-30(31)40)17-29-35-25(13-15-39(29)2)20-34(42-4)36(43-5)37(35)45-33/h6-11,18-21,28-29,40H,12-17H2,1-5H3/t28-,29+/m0/s1
SMILES:	CN1CCc2cc(c3cc2[C@@H]1Cc1ccc(cc1)Oc1cc(ccc1O)C[C@@H]1c2c(CCN1C)cc(c(c2O3)OC)OC)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL504323
PubChem CID:	275182
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0001392] Lignans, neolignans and related compounds

*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
NPO8212	Ligularia nelumbifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12088436]
NPO14431	Dunaliella salina	Species	Dunaliellaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[14664856]
NPO10618	Acnistus arborescens	Species	Solanaceae	Eukaryota	leaves	n.a.	n.a.	PMID[15104512]
NPO25510	Plectranthus ernstii	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19445517]
NPO10618	Acnistus arborescens	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20590148]
NPO15264	Garcinia paucinervis	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20594858]
NPO8212	Ligularia nelumbifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22472691]
NPO6648	Piper retrofractum	Species	Piperaceae	Eukaryota	Fruits	n.a.	n.a.	PMID[23506561]
NPO22181	Leibnitzia anandria	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24699147]
NPO6648	Piper retrofractum	Species	Piperaceae	Eukaryota	leaves	n.a.	n.a.	PMID[25127165]
NPO20712	Panax quinquefolius	Species	Araliaceae	Eukaryota	leaves and stems	n.a.	n.a.	PMID[25442304]
NPO21410	Populus balsamifera	Species	Salicaceae	Eukaryota	Buds	n.a.	n.a.	PMID[25927817]
NPO17909	Berberis vulgaris	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[30701972]
NPO31374	Stephania cepharantha	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32129063]
NPO3849	Cyclea barbata	Species	Menispermaceae	Eukaryota	roots	n.a.	n.a.	PMID[8289066]
NPO3849	Cyclea barbata	Species	Menispermaceae	Eukaryota	roots	n.a.	n.a.	PMID[8450318]
NPO3849	Cyclea barbata	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9917283]
NPO28026	Grifola frondosa	Species	Schizophyllaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO31374	Stephania cepharantha	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO17909	Berberis vulgaris	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO30288	Thalictrum thunbergii	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18832	Berberis thunbergii	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO27892	Eupatorium glandulosum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO30280	Mahonia japonica	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[HerDing]
NPO13637	Thalictrum foliolosum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7002	Ardisia hortorum	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO31574	Mahonia fortunei	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[HerDing]
NPO22043	Hylomecon japonica	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO21410	Populus balsamifera	Species	Salicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO3849	Cyclea barbata	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO859	Berberis oblonga	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO17909	Berberis vulgaris	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8212	Ligularia nelumbifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18832	Berberis thunbergii	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7002	Ardisia hortorum	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8077	Artocarpus incisa	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11640	Berberis fortunei	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22181	Leibnitzia anandria	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO27892	Eupatorium glandulosum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10618	Acnistus arborescens	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6648	Piper retrofractum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20712	Panax quinquefolius	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13637	Thalictrum foliolosum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21410	Populus balsamifera	Species	Salicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO859	Berberis oblonga	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22043	Hylomecon japonica	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3849	Cyclea barbata	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO31574	Mahonia fortunei	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO13637	Thalictrum foliolosum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO30167	Stephania sasakll	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO18832	Berberis thunbergii	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO21410	Populus balsamifera	Species	Salicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO31374	Stephania cepharantha	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO17909	Berberis vulgaris	Species	Berberidaceae	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]
NPO30280	Mahonia japonica	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO30288	Thalictrum thunbergii	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO11640	Berberis fortunei	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO20712	Panax quinquefolius	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO6648	Piper retrofractum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22181	Leibnitzia anandria	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25510	Plectranthus ernstii	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17909	Berberis vulgaris	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20704	Conus gladiator	Species	Conidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13554	Chrysactinia mexicana	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20581	Sargassum fulvellum	Species	Sargassaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22436	Lora quadra	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO21496	Pilosocereus chrysacanthus	Species	Cactaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3994	Haplophyllum latifolium	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28690	Zamia spiralis	Species	Zamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7002	Ardisia hortorum	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8212	Ligularia nelumbifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO435	Bohadschia marmorata	Species	Holothuriidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28177	Photinus marginellus	Species	Lampyridae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14056	Microstrobos niphophilus	Species	Podocarpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19888	Doronicum grandiflorum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11640	Berberis fortunei	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16401	Zataria bracteata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21410	Populus balsamifera	Species	Salicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15264	Garcinia paucinervis	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20325	Dictyodendrilla cavernosa	Species	Dictyodendrillidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21468	Dilophus guineensis	Species	Dictyotaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10518	Chrysanthemum myconis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22754	0tholaena schaffneri	Species	Pteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20965	Oxytropis lanata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10618	Acnistus arborescens	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13637	Thalictrum foliolosum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14431	Dunaliella salina	Species	Dunaliellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28143	Sideritis ferrensis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18333	Sphaerophysa salsula	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28026	Grifola frondosa	Species	Schizophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16970	Nectandra saligna	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22498	Lithocarpus haipinii	Species	Fagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO859	Berberis oblonga	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12130	Frullania dilatata	Species	Frullaniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22043	Hylomecon japonica	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21780	Strychnos gossweileri	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22942	Moesziomyces antarcticus	Species	Ustilaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8448	Trifolium stellatum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13942	Cryptantha leiocarpa	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8077	Artocarpus incisa	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22629	Spongia vaginalis	Species	Spongiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18832	Berberis thunbergii	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19668.1	Euphorbia characias subsp. wulfenii	Subspecies	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27892	Eupatorium glandulosum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28247	Radula voluta	Species	Radulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20712	Panax quinquefolius	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22767	Phomopsis cassiae	Species	Valsaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28652	Euphorbia broteri	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO595	Tephrosia falciformis	Species	Geometridae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3849	Cyclea barbata	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1114	Cetraria australiensis	Species	Parmeliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
ED50	1
IC50	11
Ki	1
Others	10
Potency	8

Activity Type	# Activity
Cell Line	7
Individual Protein	11
Organism	4
Others	8
Protein Family	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT3047	Individual Protein	Phosphodiesterase 1A	Homo sapiens	IC50	=	22000.0	nM	PMID[534404]
NPT91	Cell Line	KB	Homo sapiens	ED50	=	9210.0	nM	PMID[534405]
NPT111	Cell Line	K562	Homo sapiens	IC50	=	8930.0	nM	PMID[534406]
NPT149	Individual Protein	Endoplasmic reticulum-associated amyloid beta-peptide-binding protein	Homo sapiens	Potency	=	31622.8	nM	PMID[534407]
NPT150	Individual Protein	Anthrax lethal factor	Bacillus anthracis	Potency	=	3162.3	nM	PMID[534408]
NPT109	Individual Protein	Cytochrome P450 3A4	Homo sapiens	Potency	=	19952.6	nM	PMID[534407]
NPT1139	Individual Protein	Arachidonate 15-lipoxygenase, type II	Homo sapiens	Potency	n.a.	15848.9	nM	PMID[534407]
NPT466	Cell Line	U-937	Homo sapiens	MED	=	25.0	uM	PMID[534409]
NPT466	Cell Line	U-937	Homo sapiens	FC	=	1.2	n.a.	PMID[534409]
NPT466	Cell Line	U-937	Homo sapiens	IC50	>	50000.0	nM	PMID[534409]
NPT466	Cell Line	U-937	Homo sapiens	Activity	=	70.0	%	PMID[534409]
NPT50	Individual Protein	Tyrosyl-DNA phosphodiesterase 1	Homo sapiens	Potency	n.a.	9441.1	nM	PMID[534411]
NPT144	Individual Protein	Telomerase reverse transcriptase	Homo sapiens	Activity	=	5.0	%	PMID[534412]
NPT189	Cell Line	Vero	Chlorocebus aethiops	CC50	>	50000.0	nM	PMID[534413]
NPT439	Individual Protein	Butyrylcholinesterase	Homo sapiens	IC50	>	100000.0	nM	PMID[534414]
NPT204	Individual Protein	Acetylcholinesterase	Homo sapiens	IC50	>	100000.0	nM	PMID[534414]
NPT1591	Individual Protein	Prolyl endopeptidase	Homo sapiens	IC50	>	200000.0	nM	PMID[534414]
NPT422	Protein Family	Muscarinic acetylcholine receptor	Rattus norvegicus	Ki	=	190.0	nM	PMID[534404]
NPT2	Others	Unspecified		Inhibition	=	56.4	%	PMID[534404]
NPT2	Others	Unspecified		IC50	=	60000.0	nM	PMID[534404]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	128.0	nM	PMID[534405]
NPT2	Others	Unspecified		Selectivity Index	=	72.0	n.a.	PMID[534405]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	313.0	nM	PMID[534405]
NPT2	Others	Unspecified		Selectivity Index	=	29.0	n.a.	PMID[534405]
NPT992	Organism	Entamoeba histolytica	Entamoeba histolytica	IC50	=	22.37	ug.mL-1	PMID[534410]
NPT2	Others	Unspecified		Potency	n.a.	11220.2	nM	PMID[534411]
NPT2	Others	Unspecified		Potency	n.a.	2818.4	nM	PMID[534411]
NPT20555	ORGANISM	SARS-CoV-2	Severe acute respiratory syndrome coronavirus 2	IC50	=	7870.0	nM	PMID[534413]
NPT27	Others	Unspecified		Selectivity index	=	6.35	n.a.	PMID[534413]
NPT2	Others	Unspecified		Ratio IC50	=	0.4	n.a.	PMID[534414]

☑ 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 NPC49075 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	365
0.1-0.2	1776
0.2-0.3	8970
0.3-0.4	9442
0.4-0.5	5495
0.5-0.6	8583
0.6-0.7	6506
0.7-0.8	1271
0.8-0.85	138
0.85-0.9	45
0.9-0.95	42
0.95-1	64

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC251735
1.0	High Similarity	NPC104196
1.0	High Similarity	NPC229373
1.0	High Similarity	NPC239824
1.0	High Similarity	NPC15414
1.0	High Similarity	NPC223690
1.0	High Similarity	NPC271013
1.0	High Similarity	NPC54654
1.0	High Similarity	NPC217748
1.0	High Similarity	NPC90998
1.0	High Similarity	NPC181796
1.0	High Similarity	NPC279228
1.0	High Similarity	NPC222661
1.0	High Similarity	NPC258657
1.0	High Similarity	NPC285931
1.0	High Similarity	NPC42663
1.0	High Similarity	NPC311973
1.0	High Similarity	NPC290582
1.0	High Similarity	NPC8836
1.0	High Similarity	NPC290005
1.0	High Similarity	NPC185639
1.0	High Similarity	NPC328155
1.0	High Similarity	NPC7715
1.0	High Similarity	NPC182052
0.9939	High Similarity	NPC254441
0.9939	High Similarity	NPC286119
0.9939	High Similarity	NPC167116
0.9939	High Similarity	NPC274716
0.9879	High Similarity	NPC30779
0.982	High Similarity	NPC212237
0.982	High Similarity	NPC116465
0.9762	High Similarity	NPC275680
0.9762	High Similarity	NPC22115
0.9704	High Similarity	NPC206900
0.9704	High Similarity	NPC175890
0.9704	High Similarity	NPC82457
0.9704	High Similarity	NPC274661
0.9704	High Similarity	NPC11296
0.9704	High Similarity	NPC48490
0.9647	High Similarity	NPC60295
0.9647	High Similarity	NPC191132
0.9643	High Similarity	NPC95426
0.9643	High Similarity	NPC302245
0.9643	High Similarity	NPC16357
0.9591	High Similarity	NPC24260
0.9586	High Similarity	NPC65312
0.9586	High Similarity	NPC139783
0.9573	High Similarity	NPC10908
0.9573	High Similarity	NPC317439
0.9573	High Similarity	NPC63646
0.9573	High Similarity	NPC115284
0.9573	High Similarity	NPC276890
0.9573	High Similarity	NPC198498
0.9573	High Similarity	NPC76682
0.9573	High Similarity	NPC317145
0.9573	High Similarity	NPC227060
0.9515	High Similarity	NPC41376
0.9515	High Similarity	NPC12424
0.9515	High Similarity	NPC251580
0.9515	High Similarity	NPC129518
0.9477	High Similarity	NPC478093
0.9422	High Similarity	NPC478091
0.9422	High Similarity	NPC478092
0.9422	High Similarity	NPC30182
0.9422	High Similarity	NPC473589
0.9401	High Similarity	NPC293093
0.9329	High Similarity	NPC317272
0.9329	High Similarity	NPC240841
0.9329	High Similarity	NPC256012
0.9329	High Similarity	NPC264850
0.9329	High Similarity	NPC268503
0.9329	High Similarity	NPC42549
0.9329	High Similarity	NPC250846
0.9329	High Similarity	NPC13916
0.931	High Similarity	NPC85381
0.931	High Similarity	NPC256124
0.9306	High Similarity	NPC318805
0.9306	High Similarity	NPC41122
0.929	High Similarity	NPC243454
0.929	High Similarity	NPC475479
0.9268	High Similarity	NPC24465
0.9266	High Similarity	NPC475654
0.9235	High Similarity	NPC239584
0.9217	High Similarity	NPC83198
0.9217	High Similarity	NPC204908
0.9205	High Similarity	NPC234318
0.9181	High Similarity	NPC73492
0.9181	High Similarity	NPC299990
0.9053	High Similarity	NPC152680
0.9053	High Similarity	NPC232386
0.9053	High Similarity	NPC190783
0.9017	High Similarity	NPC302275
0.8994	High Similarity	NPC475215
0.8994	High Similarity	NPC108434
0.8966	High Similarity	NPC249996
0.892	High Similarity	NPC281581
0.8902	High Similarity	NPC247639
0.8902	High Similarity	NPC195538
0.8902	High Similarity	NPC25084
0.8901	High Similarity	NPC254581
0.887	High Similarity	NPC475597
0.887	High Similarity	NPC473716
0.8851	High Similarity	NPC476202
0.8841	High Similarity	NPC39701
0.8841	High Similarity	NPC54379
0.8841	High Similarity	NPC249797
0.8841	High Similarity	NPC127674
0.8841	High Similarity	NPC278799
0.8841	High Similarity	NPC184026
0.8841	High Similarity	NPC207757
0.8841	High Similarity	NPC5238
0.8841	High Similarity	NPC204828
0.8841	High Similarity	NPC193949
0.8841	High Similarity	NPC469817
0.8841	High Similarity	NPC276588
0.8841	High Similarity	NPC172765
0.8841	High Similarity	NPC110416
0.8841	High Similarity	NPC189266
0.8841	High Similarity	NPC2413
0.8841	High Similarity	NPC295691
0.8807	High Similarity	NPC14507
0.8807	High Similarity	NPC47077
0.8772	High Similarity	NPC239775
0.8713	High Similarity	NPC118274
0.8713	High Similarity	NPC168753
0.8663	High Similarity	NPC10871
0.8639	High Similarity	NPC475393
0.8598	High Similarity	NPC151895
0.8598	High Similarity	NPC97221
0.8598	High Similarity	NPC88249
0.8598	High Similarity	NPC220858
0.8598	High Similarity	NPC192768
0.858	High Similarity	NPC60186
0.8537	High Similarity	NPC477565
0.8537	High Similarity	NPC103379
0.8523	High Similarity	NPC474507
0.8521	High Similarity	NPC271388
0.8521	High Similarity	NPC235143
0.8521	High Similarity	NPC205255
0.8521	High Similarity	NPC119649
0.8521	High Similarity	NPC230956
0.8497	Intermediate Similarity	NPC82056
0.8488	Intermediate Similarity	NPC81218
0.8488	Intermediate Similarity	NPC12053
0.8488	Intermediate Similarity	NPC205421
0.8488	Intermediate Similarity	NPC117188
0.8488	Intermediate Similarity	NPC145832
0.8488	Intermediate Similarity	NPC474931
0.8488	Intermediate Similarity	NPC306555
0.8488	Intermediate Similarity	NPC158376
0.848	Intermediate Similarity	NPC276944
0.848	Intermediate Similarity	NPC306843
0.848	Intermediate Similarity	NPC232514
0.848	Intermediate Similarity	NPC253043
0.848	Intermediate Similarity	NPC238530
0.848	Intermediate Similarity	NPC78222
0.848	Intermediate Similarity	NPC212794
0.848	Intermediate Similarity	NPC96603
0.848	Intermediate Similarity	NPC196447
0.848	Intermediate Similarity	NPC13504
0.848	Intermediate Similarity	NPC136508
0.848	Intermediate Similarity	NPC477563
0.8476	Intermediate Similarity	NPC428
0.8476	Intermediate Similarity	NPC147390
0.8476	Intermediate Similarity	NPC24233
0.8476	Intermediate Similarity	NPC246587
0.8476	Intermediate Similarity	NPC476571
0.8476	Intermediate Similarity	NPC135538
0.8475	Intermediate Similarity	NPC257269
0.8475	Intermediate Similarity	NPC230276
0.8471	Intermediate Similarity	NPC80759
0.8471	Intermediate Similarity	NPC79402
0.8462	Intermediate Similarity	NPC221864
0.8421	Intermediate Similarity	NPC324144
0.8418	Intermediate Similarity	NPC40496
0.8418	Intermediate Similarity	NPC119068
0.8418	Intermediate Similarity	NPC32154
0.8415	Intermediate Similarity	NPC210437
0.8415	Intermediate Similarity	NPC51957
0.8415	Intermediate Similarity	NPC16107
0.8415	Intermediate Similarity	NPC476144
0.8415	Intermediate Similarity	NPC321505
0.8415	Intermediate Similarity	NPC106295
0.8415	Intermediate Similarity	NPC179825
0.8415	Intermediate Similarity	NPC476151
0.8415	Intermediate Similarity	NPC191376
0.8409	Intermediate Similarity	NPC148709
0.8409	Intermediate Similarity	NPC476577
0.8409	Intermediate Similarity	NPC173416
0.8394	Intermediate Similarity	NPC38964
0.8391	Intermediate Similarity	NPC109925
0.8372	Intermediate Similarity	NPC284183
0.8372	Intermediate Similarity	NPC4138
0.8372	Intermediate Similarity	NPC121275
0.8364	Intermediate Similarity	NPC7467
0.8314	Intermediate Similarity	NPC1229
0.8305	Intermediate Similarity	NPC241704
0.8304	Intermediate Similarity	NPC166014
0.8304	Intermediate Similarity	NPC27410
0.8293	Intermediate Similarity	NPC185838

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 NPC49075 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	208
0.1-0.2	792
0.2-0.3	1192
0.3-0.4	2208
0.4-0.5	2416
0.5-0.6	1548
0.6-0.7	643
0.7-0.8	133
0.8-0.85	3
0.85-0.9	1
0.9-0.95	3
0.95-1	3

Similarity Score	Similarity Level	Drug ID	Developmental Stage
1.0	High Similarity	NPD8054	Approved
1.0	High Similarity	NPD8053	Approved
0.9573	High Similarity	NPD8251	Approved
0.9573	High Similarity	NPD8252	Approved
0.9573	High Similarity	NPD8099	Discontinued
0.9515	High Similarity	NPD8156	Discontinued
0.8579	High Similarity	NPD8095	Phase 1
0.8418	Intermediate Similarity	NPD8453	Clinical (unspecified phase)
0.8415	Intermediate Similarity	NPD4584	Approved
0.8353	Intermediate Similarity	NPD6788	Approved
0.8187	Intermediate Similarity	NPD7906	Approved
0.8118	Intermediate Similarity	NPD4773	Phase 2
0.8118	Intermediate Similarity	NPD4772	Phase 2
0.8049	Intermediate Similarity	NPD4664	Clinical (unspecified phase)
0.8023	Intermediate Similarity	NPD6818	Clinical (unspecified phase)
0.8021	Intermediate Similarity	NPD7667	Clinical (unspecified phase)
0.8011	Intermediate Similarity	NPD6071	Discontinued
0.7989	Intermediate Similarity	NPD7832	Clinical (unspecified phase)
0.7989	Intermediate Similarity	NPD7833	Phase 2
0.7989	Intermediate Similarity	NPD7831	Phase 2
0.7967	Intermediate Similarity	NPD7310	Approved
0.7967	Intermediate Similarity	NPD7313	Approved
0.7967	Intermediate Similarity	NPD7311	Approved
0.7967	Intermediate Similarity	NPD7312	Approved
0.7965	Intermediate Similarity	NPD7298	Approved
0.7923	Intermediate Similarity	NPD7309	Approved
0.7921	Intermediate Similarity	NPD27	Approved
0.7921	Intermediate Similarity	NPD2489	Approved
0.791	Intermediate Similarity	NPD3051	Approved
0.7895	Intermediate Similarity	NPD7261	Clinical (unspecified phase)
0.787	Intermediate Similarity	NPD7447	Phase 1
0.787	Intermediate Similarity	NPD1754	Clinical (unspecified phase)
0.7869	Intermediate Similarity	NPD4577	Approved
0.7869	Intermediate Similarity	NPD4578	Approved
0.7865	Intermediate Similarity	NPD2969	Approved
0.7865	Intermediate Similarity	NPD2970	Approved
0.7838	Intermediate Similarity	NPD4663	Approved
0.7797	Intermediate Similarity	NPD7201	Clinical (unspecified phase)
0.7771	Intermediate Similarity	NPD2560	Approved
0.7771	Intermediate Similarity	NPD2563	Approved
0.7717	Intermediate Similarity	NPD7549	Discontinued
0.7709	Intermediate Similarity	NPD4010	Discontinued
0.7706	Intermediate Similarity	NPD7212	Phase 2
0.7706	Intermediate Similarity	NPD7213	Phase 3
0.7661	Intermediate Similarity	NPD1424	Approved
0.7651	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7651	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7624	Intermediate Similarity	NPD2898	Approved
0.7602	Intermediate Similarity	NPD2420	Approved
0.7602	Intermediate Similarity	NPD2421	Approved
0.7588	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7584	Intermediate Similarity	NPD4055	Discovery
0.7572	Intermediate Similarity	NPD6030	Approved
0.7572	Intermediate Similarity	NPD6031	Approved
0.7544	Intermediate Similarity	NPD7124	Phase 2
0.7543	Intermediate Similarity	NPD4678	Approved
0.7543	Intermediate Similarity	NPD4675	Approved
0.75	Intermediate Similarity	NPD5677	Discontinued
0.7486	Intermediate Similarity	NPD4017	Approved
0.7485	Intermediate Similarity	NPD5241	Discontinued
0.7471	Intermediate Similarity	NPD3639	Approved
0.7471	Intermediate Similarity	NPD3640	Phase 3
0.7471	Intermediate Similarity	NPD3641	Approved
0.7459	Intermediate Similarity	NPD6107	Approved
0.7459	Intermediate Similarity	NPD7802	Discontinued
0.7449	Intermediate Similarity	NPD3452	Approved
0.7449	Intermediate Similarity	NPD3450	Approved
0.7449	Intermediate Similarity	NPD2493	Approved
0.7449	Intermediate Similarity	NPD2494	Approved
0.7442	Intermediate Similarity	NPD3845	Phase 1
0.7435	Intermediate Similarity	NPD2488	Approved
0.7435	Intermediate Similarity	NPD2490	Approved
0.7432	Intermediate Similarity	NPD4481	Phase 3
0.743	Intermediate Similarity	NPD4581	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD4005	Discontinued
0.7356	Intermediate Similarity	NPD6997	Phase 2
0.7354	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7349	Intermediate Similarity	NPD4475	Approved
0.7349	Intermediate Similarity	NPD4474	Approved
0.7337	Intermediate Similarity	NPD4582	Approved
0.7337	Intermediate Similarity	NPD4583	Approved
0.7326	Intermediate Similarity	NPD6748	Discontinued
0.7318	Intermediate Similarity	NPD5772	Approved
0.7318	Intermediate Similarity	NPD5773	Approved
0.7317	Intermediate Similarity	NPD7047	Phase 3
0.7303	Intermediate Similarity	NPD6072	Discontinued
0.7299	Intermediate Similarity	NPD7598	Phase 2
0.7294	Intermediate Similarity	NPD1632	Clinical (unspecified phase)
0.7293	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7289	Intermediate Similarity	NPD5718	Phase 2
0.7286	Intermediate Similarity	NPD4004	Approved
0.7286	Intermediate Similarity	NPD4002	Approved
0.7278	Intermediate Similarity	NPD2200	Suspended
0.7273	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD2122	Discontinued
0.7273	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD5177	Phase 3
0.7257	Intermediate Similarity	NPD4123	Phase 3
0.7252	Intermediate Similarity	NPD8152	Approved
0.7252	Intermediate Similarity	NPD8153	Approved
0.7245	Intermediate Similarity	NPD2973	Approved
0.7245	Intermediate Similarity	NPD2975	Approved
0.7245	Intermediate Similarity	NPD2974	Approved
0.7241	Intermediate Similarity	NPD2422	Clinical (unspecified phase)
0.7236	Intermediate Similarity	NPD5005	Approved
0.7236	Intermediate Similarity	NPD5006	Approved
0.7234	Intermediate Similarity	NPD6996	Clinical (unspecified phase)
0.7225	Intermediate Similarity	NPD7466	Approved
0.7222	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD7046	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD5312	Approved
0.7219	Intermediate Similarity	NPD5313	Approved
0.7216	Intermediate Similarity	NPD6090	Discontinued
0.7212	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7209	Intermediate Similarity	NPD7045	Clinical (unspecified phase)
0.7202	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7202	Intermediate Similarity	NPD1613	Approved
0.72	Intermediate Similarity	NPD3124	Discontinued
0.7191	Intermediate Similarity	NPD8158	Clinical (unspecified phase)
0.7173	Intermediate Similarity	NPD6851	Approved
0.7173	Intermediate Similarity	NPD6853	Approved
0.7172	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7171	Intermediate Similarity	NPD7827	Phase 1
0.7169	Intermediate Similarity	NPD4908	Phase 1
0.7167	Intermediate Similarity	NPD7945	Clinical (unspecified phase)
0.7158	Intermediate Similarity	NPD7132	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6297	Approved
0.7136	Intermediate Similarity	NPD4580	Approved
0.7128	Intermediate Similarity	NPD42	Phase 2
0.7128	Intermediate Similarity	NPD6042	Phase 2
0.712	Intermediate Similarity	NPD2968	Approved
0.712	Intermediate Similarity	NPD2971	Approved
0.712	Intermediate Similarity	NPD3534	Clinical (unspecified phase)
0.7112	Intermediate Similarity	NPD5602	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD6523	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD3692	Discontinued
0.7083	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7079	Intermediate Similarity	NPD4040	Phase 1
0.7076	Intermediate Similarity	NPD6111	Discontinued
0.7076	Intermediate Similarity	NPD6895	Approved
0.7076	Intermediate Similarity	NPD6896	Approved
0.7071	Intermediate Similarity	NPD6621	Clinical (unspecified phase)
0.7069	Intermediate Similarity	NPD4162	Approved
0.7069	Intermediate Similarity	NPD3060	Approved
0.7069	Intermediate Similarity	NPD4237	Approved
0.7069	Intermediate Similarity	NPD4236	Phase 3
0.7062	Intermediate Similarity	NPD4160	Clinical (unspecified phase)
0.7052	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7045	Intermediate Similarity	NPD6666	Approved
0.7045	Intermediate Similarity	NPD6667	Approved
0.7045	Intermediate Similarity	NPD6783	Clinical (unspecified phase)
0.7043	Intermediate Similarity	NPD4166	Phase 2
0.7041	Intermediate Similarity	NPD2674	Phase 3
0.7037	Intermediate Similarity	NPD4873	Discontinued
0.7035	Intermediate Similarity	NPD4420	Approved
0.7033	Intermediate Similarity	NPD2978	Approved
0.7033	Intermediate Similarity	NPD4585	Approved
0.7033	Intermediate Similarity	NPD2977	Approved
0.7024	Intermediate Similarity	NPD2669	Clinical (unspecified phase)
0.7024	Intermediate Similarity	NPD3027	Phase 3
0.7021	Intermediate Similarity	NPD5938	Phase 3
0.7017	Intermediate Similarity	NPD5089	Approved
0.7017	Intermediate Similarity	NPD5090	Approved
0.7011	Intermediate Similarity	NPD7037	Approved
0.7011	Intermediate Similarity	NPD8005	Clinical (unspecified phase)
0.7005	Intermediate Similarity	NPD8051	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD7479	Phase 2
0.7	Intermediate Similarity	NPD2238	Phase 2
0.6989	Remote Similarity	NPD2677	Approved
0.6989	Remote Similarity	NPD5160	Discontinued
0.6989	Remote Similarity	NPD5084	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD7718	Clinical (unspecified phase)
0.6974	Remote Similarity	NPD7291	Discontinued
0.6939	Remote Similarity	NPD6377	Clinical (unspecified phase)
0.6936	Remote Similarity	NPD1753	Discontinued
0.6935	Remote Similarity	NPD4666	Phase 3
0.6932	Remote Similarity	NPD6658	Clinical (unspecified phase)
0.6927	Remote Similarity	NPD3647	Clinical (unspecified phase)
0.6915	Remote Similarity	NPD3837	Clinical (unspecified phase)
0.6904	Remote Similarity	NPD5525	Clinical (unspecified phase)
0.6901	Remote Similarity	NPD7907	Approved
0.6895	Remote Similarity	NPD6723	Discontinued
0.6895	Remote Similarity	NPD7493	Clinical (unspecified phase)
0.6895	Remote Similarity	NPD5940	Clinical (unspecified phase)
0.6891	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6889	Remote Similarity	NPD5976	Discontinued
0.6888	Remote Similarity	NPD6841	Approved
0.6888	Remote Similarity	NPD6842	Approved
0.6888	Remote Similarity	NPD6843	Phase 3
0.6882	Remote Similarity	NPD5709	Phase 3
0.6882	Remote Similarity	NPD6812	Clinical (unspecified phase)
0.6882	Remote Similarity	NPD3145	Approved
0.6882	Remote Similarity	NPD3144	Approved
0.6878	Remote Similarity	NPD6166	Phase 2
0.6878	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6878	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD6496	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD3656	Approved
0.6856	Remote Similarity	NPD7281	Phase 3
0.6856	Remote Similarity	NPD7280	Phase 3

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