NPASS Compound

Structure

CID216538 OpenBabel06191716002D 27 29 0 0 0 0 0 0 0 0999 V2000 1.7321 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 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 -2.5981 0.5000 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 0.0000 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 2.5981 1.5000 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 -1.7321 0.0000 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 0.0000 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 1.7321 2.0000 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 0.0000 2.0000 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 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 3.0000 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 11 1 0 0 0 0 2 11 1 0 0 0 0 3 26 1 0 0 0 0 4 9 1 0 0 0 0 4 11 2 0 0 0 0 5 7 1 0 0 0 0 5 12 2 0 0 0 0 6 8 2 0 0 0 0 6 12 1 0 0 0 0 7 13 2 0 0 0 0 8 13 1 0 0 0 0 9 14 1 0 0 0 0 10 15 2 0 0 0 0 10 16 1 0 0 0 0 12 20 1 0 0 0 0 13 22 1 0 0 0 0 14 15 1 0 0 0 0 14 21 2 0 0 0 0 15 23 1 0 0 0 0 16 17 2 0 0 0 0 16 26 1 0 0 0 0 17 18 1 0 0 0 0 17 21 1 0 0 0 0 18 19 1 0 0 0 0 18 24 2 0 0 0 0 19 20 2 0 0 0 0 19 25 1 0 0 0 0 20 27 1 0 0 0 0 21 27 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	368.13
Volume:	375.116
LogP:	4.611
LogD:	2.914
LogS:	-3.466
# Rotatable Bonds:	4
TPSA:	100.13
# H-Bond Aceptor:	6
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.6
Synthetic Accessibility Score:	2.742
Fsp3:	0.19
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.809
MDCK Permeability:	1.1548314432729967e-05
Pgp-inhibitor:	0.067
Pgp-substrate:	0.018
Human Intestinal Absorption (HIA):	0.024
20% Bioavailability (F20%):	0.015
30% Bioavailability (F30%):	0.192

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.006
Plasma Protein Binding (PPB):	93.25672149658203%
Volume Distribution (VD):	0.757
Pgp-substrate:	7.119811534881592%

ADMET: Metabolism

CYP1A2-inhibitor:	0.871
CYP1A2-substrate:	0.38
CYP2C19-inhibitor:	0.85
CYP2C19-substrate:	0.057
CYP2C9-inhibitor:	0.853
CYP2C9-substrate:	0.906
CYP2D6-inhibitor:	0.641
CYP2D6-substrate:	0.276
CYP3A4-inhibitor:	0.397
CYP3A4-substrate:	0.101

ADMET: Excretion

Clearance (CL):	7.837
Half-life (T1/2):	0.743

ADMET: Toxicity

hERG Blockers:	0.006
Human Hepatotoxicity (H-HT):	0.765
Drug-inuced Liver Injury (DILI):	0.979
AMES Toxicity:	0.634
Rat Oral Acute Toxicity:	0.258
Maximum Recommended Daily Dose:	0.03
Skin Sensitization:	0.608
Carcinogencity:	0.116
Eye Corrosion:	0.003
Eye Irritation:	0.724
Respiratory Toxicity:	0.168

Download Data

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

Natural Product: NPC216538

Natural Product ID:	NPC216538
*Common Name:**	Sophoflavescenol
IUPAC Name:	3,7-dihydroxy-2-(4-hydroxyphenyl)-5-methoxy-8-(3-methylbut-2-enyl)chromen-4-one
Synonyms:	Sophoflavescenol
Standard InCHIKey:	VMLJAWUWVVHRNG-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C21H20O6/c1-11(2)4-9-14-15(23)10-16(26-3)17-18(24)19(25)20(27-21(14)17)12-5-7-13(22)8-6-12/h4-8,10,22-23,25H,9H2,1-3H3
SMILES:	COc1cc(O)c(c2c1c(=O)c(O)c(o2)c1ccc(cc1)O)CC=C(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL77651
PubChem CID:	9929189
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001615] Flavones [CHEMONTID:0003504] 8-prenylated flavones

*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
NPO19231	Sophora flavescens	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10654410]
NPO19231	Sophora flavescens	Species	Fabaceae	Eukaryota	n.a.	root	n.a.	PMID[10843587]
NPO20142	Embelia schimperi	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11054840]
NPO18668	Asimina parviflora	Species	Annonaceae	Eukaryota	twigs	n.a.	n.a.	PMID[1453182]
NPO19667	Hypericum styphelioides	Species	Hypericaceae	Eukaryota	leaves	n.a.	n.a.	PMID[15165152]
NPO19667	Hypericum styphelioides	Species	Hypericaceae	Eukaryota	n.a.	leaf	n.a.	PMID[15165152]
NPO19231	Sophora flavescens	Species	Fabaceae	Eukaryota	Roots	n.a.	n.a.	PMID[15568770]
NPO18286	Lycogala epidendrum	Species	Enteridiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[15911254]
NPO19231	Sophora flavescens	Species	Fabaceae	Eukaryota	n.a.	root	n.a.	PMID[16392664]
NPO19231	Sophora flavescens	Species	Fabaceae	Eukaryota	roots	Hualien Hsien, Taiwan	2003-JUL	PMID[16933887]
NPO19231	Sophora flavescens	Species	Fabaceae	Eukaryota	n.a.	root	n.a.	PMID[16933887]
NPO19231	Sophora flavescens	Species	Fabaceae	Eukaryota	n.a.	root	n.a.	PMID[17951038]
NPO19231	Sophora flavescens	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18175961]
NPO20879	Clerodendrum bungei	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18348535]
NPO18176	Ephedra sinica	Species	Ephedraceae	Eukaryota	n.a.	root	n.a.	PMID[18975262]
NPO3152	Morella rubra	Species	Myricaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19407970]
NPO3152	Morella rubra	Species	Myricaceae	Eukaryota	n.a.	bark	n.a.	PMID[21553897]
NPO19231	Sophora flavescens	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24295087]
NPO18176	Ephedra sinica	Species	Ephedraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24333010]
NPO20598	Lythrum salicaria	Species	Lythraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24459770]
NPO19231	Sophora flavescens	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27575476]
NPO19231	Sophora flavescens	Species	Fabaceae	Eukaryota	Roots	n.a.	n.a.	PMID[30298740]
NPO19231	Sophora flavescens	Species	Fabaceae	Eukaryota	Roots	n.a.	n.a.	PMID[9868163]
NPO19231	Sophora flavescens	Species	Fabaceae	Eukaryota	n.a.	root	n.a.	Database[Article]
NPO21170	Embelia parviflora	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO19231	Sophora flavescens	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18176	Ephedra sinica	Species	Ephedraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO12056	Chondrodendron tomentosum	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO21375	Euphorbia nematocypha	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO20598	Lythrum salicaria	Species	Lythraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18286	Lycogala epidendrum	Species	Enteridiidae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO17334	Onopordum acanthium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18668	Asimina parviflora	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20879	Clerodendrum bungei	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3152	Morella rubra	Species	Myricaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18286	Lycogala epidendrum	Species	Enteridiidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21170	Embelia parviflora	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20142	Embelia schimperi	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20680	Erythrina melanacantha	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21375	Euphorbia nematocypha	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20489	Epilobium hirsutum	Species	Onagraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19231	Sophora flavescens	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12056	Chondrodendron tomentosum	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20598	Lythrum salicaria	Species	Lythraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17334	Onopordum acanthium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18176	Ephedra sinica	Species	Ephedraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17334	Onopordum acanthium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO19231	Sophora flavescens	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO18176	Ephedra sinica	Species	Ephedraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO21170	Embelia parviflora	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO20598	Lythrum salicaria	Species	Lythraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO20680	Erythrina melanacantha	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO21375	Euphorbia nematocypha	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO18286	Lycogala epidendrum	Species	Enteridiidae	Eukaryota	n.a.	n.a.	n.a.	Database[Title]
NPO19231	Sophora flavescens	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO18176	Ephedra sinica	Species	Ephedraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO16141	Piper regnellii	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21562	Diospyros assimilis	Species	Ebenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14241	Planchonia grandis	Species	Asterolecaniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17560	Pancratium sickenbergeri	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19912	Vellozia nanuzae	Species	Velloziaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18286	Lycogala epidendrum	Species	Enteridiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18866	Pteridium esculentum	Species	Dennstaedtiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19810	Myxococcus stipitatus	Species	Myxococcaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO9968	Shigella dysenteriae	Species	Enterobacteriaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO21495	Abelia chinensis	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18668	Asimina parviflora	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20843	Monsonia senegalensis	Species	Geraniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17334	Onopordum acanthium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27367	Latrunculia magnifica	Species	Latrunculiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19036	Esenbeckia leiocarpa	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19511	Dolabella californica	Species	Aplysiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20598	Lythrum salicaria	Species	Lythraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22961	Cordia leucocephala	Species	Cordiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18473	Plathymenia reticulata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21631	Faramea salicifolia	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21038	Lemaireocereus longispinus	Species	Cactaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5903	Conus mus	Species	Conidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22937	Vernonia fagifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21170	Embelia parviflora	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28202	Helichrysum tenuifolium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3152	Morella rubra	Species	Myricaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19667	Hypericum styphelioides	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20879	Clerodendrum bungei	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18176	Ephedra sinica	Species	Ephedraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20084	Atraphaxis spinosa	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18143	Dendronephthya griffini	Species	Nephtheidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20142	Embelia schimperi	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16569	Gymnocalycium schickendantzii	Species	Cactaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19995	Baccharis neglecta	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20421	Aplophyllum alberti-regelii	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO12056	Chondrodendron tomentosum	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20489	Epilobium hirsutum	Species	Onagraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11523	Erysimum leptophyllum	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21375	Euphorbia nematocypha	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17258	Rhinella marina	Species	Bufonidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17849	Centaurea maculosa	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28072	Theonella conica	Species	Theonellidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19231	Sophora flavescens	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20680	Erythrina melanacantha	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4051	Tricholoma columbetta	Species	Tricholomataceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21243	Siphonaria capensis	Species	Siphonariidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21108	Eria anomala	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20624	Simarouba glauca	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12313	Haplophyllum obtusifolium	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13449	Syzygium polycephaloides	Species	Myrtaceae	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
EC50	1
IC50	4
Ki	1
Others	2

Activity Type	# Activity
Individual Protein	2
Organism	1
Others	4
Protein Family	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1536	Individual Protein	Phosphodiesterase 5A	Rattus norvegicus	IC50	=	13.0	nM	PMID[565906]
NPT1536	Individual Protein	Phosphodiesterase 5A	Rattus norvegicus	Ki	=	5.0	nM	PMID[565906]
NPT2	Others	Unspecified		IC50	=	410.0	nM	PMID[565906]
NPT1537	Protein Family	Phosphodiesterase 4	Rattus norvegicus	IC50	=	2550.0	nM	PMID[565906]
NPT2	Others	Unspecified		Ratio	=	31.5	n.a.	PMID[565906]
NPT2	Others	Unspecified		Ratio	=	196.2	n.a.	PMID[565906]
NPT190	Organism	Human herpesvirus 1	Human herpesvirus 1	EC50	>	300.0	ug.mL-1	PMID[565907]
NPT2	Others	Unspecified		IC50	=	13.0	nM	PMID[565908]

☑ 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 NPC216538 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	422
0.1-0.2	1815
0.2-0.3	4517
0.3-0.4	10905
0.4-0.5	6954
0.5-0.6	3809
0.6-0.7	5319
0.7-0.8	4347
0.8-0.85	2137
0.85-0.9	1763
0.9-0.95	630
0.95-1	79

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC273538
0.9928	High Similarity	NPC293053
0.9928	High Similarity	NPC124729
0.9928	High Similarity	NPC178343
0.9928	High Similarity	NPC190637
0.9928	High Similarity	NPC306488
0.9928	High Similarity	NPC5820
0.9928	High Similarity	NPC24821
0.9928	High Similarity	NPC212932
0.9928	High Similarity	NPC9117
0.9856	High Similarity	NPC326500
0.9855	High Similarity	NPC473042
0.9855	High Similarity	NPC200694
0.9787	High Similarity	NPC244407
0.9787	High Similarity	NPC296869
0.9784	High Similarity	NPC158874
0.9718	High Similarity	NPC470461
0.9716	High Similarity	NPC166757
0.9716	High Similarity	NPC14001
0.971	High Similarity	NPC241100
0.971	High Similarity	NPC159275
0.965	High Similarity	NPC61258
0.9648	High Similarity	NPC470460
0.9645	High Similarity	NPC220418
0.9645	High Similarity	NPC470458
0.964	High Similarity	NPC262094
0.964	High Similarity	NPC110969
0.964	High Similarity	NPC282300
0.964	High Similarity	NPC90582
0.9638	High Similarity	NPC152042
0.9638	High Similarity	NPC78913
0.9638	High Similarity	NPC18260
0.9638	High Similarity	NPC217186
0.9638	High Similarity	NPC241838
0.9638	High Similarity	NPC143799
0.9638	High Similarity	NPC301217
0.9638	High Similarity	NPC303633
0.9638	High Similarity	NPC55018
0.9638	High Similarity	NPC53181
0.9638	High Similarity	NPC96565
0.9638	High Similarity	NPC220062
0.9638	High Similarity	NPC216978
0.958	High Similarity	NPC269420
0.9574	High Similarity	NPC224714
0.9574	High Similarity	NPC234629
0.9574	High Similarity	NPC311741
0.9571	High Similarity	NPC11561
0.9571	High Similarity	NPC226636
0.9568	High Similarity	NPC230285
0.9568	High Similarity	NPC146679
0.9568	High Similarity	NPC281207
0.9568	High Similarity	NPC261227
0.9568	High Similarity	NPC59951
0.9568	High Similarity	NPC103342
0.9568	High Similarity	NPC270883
0.9568	High Similarity	NPC103904
0.9568	High Similarity	NPC172986
0.9568	High Similarity	NPC269652
0.9568	High Similarity	NPC184536
0.9568	High Similarity	NPC150522
0.9565	High Similarity	NPC276905
0.9565	High Similarity	NPC201395
0.951	High Similarity	NPC168085
0.9507	High Similarity	NPC472629
0.9504	High Similarity	NPC18585
0.9504	High Similarity	NPC166138
0.9504	High Similarity	NPC106985
0.9504	High Similarity	NPC219915
0.9504	High Similarity	NPC11700
0.95	High Similarity	NPC147688
0.95	High Similarity	NPC469404
0.95	High Similarity	NPC103362
0.95	High Similarity	NPC156590
0.95	High Similarity	NPC136840
0.95	High Similarity	NPC118840
0.95	High Similarity	NPC205006
0.95	High Similarity	NPC64908
0.9452	High Similarity	NPC236756
0.9452	High Similarity	NPC193200
0.9452	High Similarity	NPC311579
0.9448	High Similarity	NPC262039
0.9448	High Similarity	NPC319910
0.9448	High Similarity	NPC254412
0.9448	High Similarity	NPC278476
0.9448	High Similarity	NPC262038
0.9444	High Similarity	NPC5173
0.9444	High Similarity	NPC317492
0.9441	High Similarity	NPC308200
0.9441	High Similarity	NPC24673
0.9441	High Similarity	NPC79469
0.9441	High Similarity	NPC201731
0.9441	High Similarity	NPC473077
0.9441	High Similarity	NPC296998
0.9441	High Similarity	NPC237635
0.9441	High Similarity	NPC97716
0.9441	High Similarity	NPC104406
0.9437	High Similarity	NPC87486
0.9437	High Similarity	NPC271288
0.9437	High Similarity	NPC470890
0.9437	High Similarity	NPC319752
0.9437	High Similarity	NPC124780
0.9433	High Similarity	NPC166482
0.9433	High Similarity	NPC293852
0.9433	High Similarity	NPC76338
0.9433	High Similarity	NPC220998
0.9433	High Similarity	NPC228504
0.9433	High Similarity	NPC227579
0.9433	High Similarity	NPC10937
0.9433	High Similarity	NPC78
0.9433	High Similarity	NPC76372
0.9433	High Similarity	NPC177354
0.9433	High Similarity	NPC223500
0.9433	High Similarity	NPC328164
0.9433	High Similarity	NPC214236
0.9433	High Similarity	NPC64915
0.9433	High Similarity	NPC40833
0.9433	High Similarity	NPC265040
0.9433	High Similarity	NPC125855
0.9433	High Similarity	NPC182852
0.9433	High Similarity	NPC1089
0.9433	High Similarity	NPC144499
0.9433	High Similarity	NPC306829
0.9433	High Similarity	NPC78803
0.9433	High Similarity	NPC148757
0.9433	High Similarity	NPC296917
0.9433	High Similarity	NPC66515
0.9433	High Similarity	NPC32739
0.9433	High Similarity	NPC217083
0.9433	High Similarity	NPC107572
0.9433	High Similarity	NPC299080
0.9433	High Similarity	NPC324134
0.9433	High Similarity	NPC59739
0.9433	High Similarity	NPC62840
0.9433	High Similarity	NPC161506
0.9433	High Similarity	NPC194432
0.9433	High Similarity	NPC324436
0.9433	High Similarity	NPC37496
0.9433	High Similarity	NPC166934
0.9433	High Similarity	NPC167624
0.9429	High Similarity	NPC235239
0.9429	High Similarity	NPC305355
0.9429	High Similarity	NPC475680
0.9429	High Similarity	NPC259166
0.9429	High Similarity	NPC69769
0.9429	High Similarity	NPC219917
0.9429	High Similarity	NPC326109
0.9429	High Similarity	NPC204985
0.9429	High Similarity	NPC172250
0.9429	High Similarity	NPC144118
0.9429	High Similarity	NPC80962
0.9429	High Similarity	NPC215311
0.9429	High Similarity	NPC48624
0.9429	High Similarity	NPC213659
0.9424	High Similarity	NPC131130
0.942	High Similarity	NPC473887
0.942	High Similarity	NPC29353
0.942	High Similarity	NPC124784
0.942	High Similarity	NPC47815
0.942	High Similarity	NPC216361
0.942	High Similarity	NPC127447
0.942	High Similarity	NPC194281
0.942	High Similarity	NPC13408
0.942	High Similarity	NPC281917
0.942	High Similarity	NPC116775
0.942	High Similarity	NPC231772
0.942	High Similarity	NPC234133
0.942	High Similarity	NPC187432
0.942	High Similarity	NPC256042
0.942	High Similarity	NPC174999
0.9388	High Similarity	NPC111341
0.9388	High Similarity	NPC48579
0.9388	High Similarity	NPC207809
0.9388	High Similarity	NPC304207
0.9388	High Similarity	NPC476169
0.9388	High Similarity	NPC304745
0.9388	High Similarity	NPC133392
0.9388	High Similarity	NPC259710
0.9388	High Similarity	NPC217706
0.9384	High Similarity	NPC171651
0.9384	High Similarity	NPC216035
0.9384	High Similarity	NPC142527
0.9384	High Similarity	NPC243171
0.9384	High Similarity	NPC217149
0.9384	High Similarity	NPC157784
0.9384	High Similarity	NPC210597
0.9384	High Similarity	NPC35567
0.9384	High Similarity	NPC138288
0.9384	High Similarity	NPC37684
0.9384	High Similarity	NPC45934
0.9384	High Similarity	NPC63187
0.9379	High Similarity	NPC476185
0.9379	High Similarity	NPC37348
0.9379	High Similarity	NPC105136
0.9379	High Similarity	NPC471115
0.9379	High Similarity	NPC321896
0.9379	High Similarity	NPC472633
0.9379	High Similarity	NPC29777
0.9375	High Similarity	NPC266572
0.9375	High Similarity	NPC145467
0.9375	High Similarity	NPC6511

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 NPC216538 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	391
0.1-0.2	968
0.2-0.3	1679
0.3-0.4	2699
0.4-0.5	1821
0.5-0.6	1060
0.6-0.7	352
0.7-0.8	112
0.8-0.85	44
0.85-0.9	17
0.9-0.95	6
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
1.0	High Similarity	NPD4378	Clinical (unspecified phase)
0.9167	High Similarity	NPD7410	Clinical (unspecified phase)
0.9078	High Similarity	NPD1552	Clinical (unspecified phase)
0.9078	High Similarity	NPD1550	Clinical (unspecified phase)
0.9071	High Similarity	NPD1510	Phase 2
0.906	High Similarity	NPD2393	Clinical (unspecified phase)
0.9014	High Similarity	NPD1549	Phase 2
0.9007	High Similarity	NPD7075	Discontinued
0.9007	High Similarity	NPD2796	Approved
0.8986	High Similarity	NPD4380	Phase 2
0.8973	High Similarity	NPD1512	Approved
0.8933	High Similarity	NPD7096	Clinical (unspecified phase)
0.8921	High Similarity	NPD1240	Approved
0.8874	High Similarity	NPD8443	Clinical (unspecified phase)
0.8867	High Similarity	NPD6801	Discontinued
0.8836	High Similarity	NPD1511	Approved
0.8808	High Similarity	NPD2801	Approved
0.88	High Similarity	NPD7411	Suspended
0.8794	High Similarity	NPD1607	Approved
0.8742	High Similarity	NPD1934	Approved
0.8734	High Similarity	NPD7804	Clinical (unspecified phase)
0.8707	High Similarity	NPD6799	Approved
0.8684	High Similarity	NPD7819	Suspended
0.8636	High Similarity	NPD4381	Clinical (unspecified phase)
0.8627	High Similarity	NPD3817	Phase 2
0.8571	High Similarity	NPD3882	Suspended
0.8562	High Similarity	NPD2800	Approved
0.8544	High Similarity	NPD6166	Phase 2
0.8544	High Similarity	NPD6167	Clinical (unspecified phase)
0.8544	High Similarity	NPD6168	Clinical (unspecified phase)
0.8503	High Similarity	NPD3750	Approved
0.8487	Intermediate Similarity	NPD6599	Discontinued
0.8471	Intermediate Similarity	NPD6959	Discontinued
0.8452	Intermediate Similarity	NPD7768	Phase 2
0.8435	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.8428	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8367	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8356	Intermediate Similarity	NPD2935	Discontinued
0.8311	Intermediate Similarity	NPD1243	Approved
0.8289	Intermediate Similarity	NPD5403	Approved
0.8289	Intermediate Similarity	NPD920	Approved
0.8282	Intermediate Similarity	NPD6797	Phase 2
0.8276	Intermediate Similarity	NPD6651	Approved
0.8252	Intermediate Similarity	NPD2313	Discontinued
0.8252	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.8232	Intermediate Similarity	NPD7251	Discontinued
0.8231	Intermediate Similarity	NPD1551	Phase 2
0.821	Intermediate Similarity	NPD3818	Discontinued
0.8187	Intermediate Similarity	NPD6232	Discontinued
0.8182	Intermediate Similarity	NPD7808	Phase 3
0.8182	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.8176	Intermediate Similarity	NPD5494	Approved
0.8165	Intermediate Similarity	NPD3749	Approved
0.8163	Intermediate Similarity	NPD3748	Approved
0.8163	Intermediate Similarity	NPD2799	Discontinued
0.816	Intermediate Similarity	NPD7054	Approved
0.8158	Intermediate Similarity	NPD2533	Approved
0.8158	Intermediate Similarity	NPD2532	Approved
0.8158	Intermediate Similarity	NPD5401	Approved
0.8158	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.8158	Intermediate Similarity	NPD2534	Approved
0.8153	Intermediate Similarity	NPD5402	Approved
0.8148	Intermediate Similarity	NPD7473	Discontinued
0.8146	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.811	Intermediate Similarity	NPD7074	Phase 3
0.811	Intermediate Similarity	NPD7472	Approved
0.8072	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8061	Intermediate Similarity	NPD5953	Discontinued
0.8054	Intermediate Similarity	NPD2344	Approved
0.8049	Intermediate Similarity	NPD7286	Phase 2
0.8013	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.8012	Intermediate Similarity	NPD1247	Approved
0.8012	Intermediate Similarity	NPD6559	Discontinued
0.8	Intermediate Similarity	NPD919	Approved
0.8	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7987	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7949	Intermediate Similarity	NPD3226	Approved
0.7919	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7902	Intermediate Similarity	NPD1203	Approved
0.7877	Intermediate Similarity	NPD3268	Approved
0.7867	Intermediate Similarity	NPD6100	Approved
0.7867	Intermediate Similarity	NPD6099	Approved
0.7862	Intermediate Similarity	NPD4908	Phase 1
0.7857	Intermediate Similarity	NPD7390	Discontinued
0.7847	Intermediate Similarity	NPD2798	Approved
0.7843	Intermediate Similarity	NPD2309	Approved
0.7842	Intermediate Similarity	NPD1548	Phase 1
0.7831	Intermediate Similarity	NPD5844	Phase 1
0.7816	Intermediate Similarity	NPD4363	Phase 3
0.7816	Intermediate Similarity	NPD4360	Phase 2
0.7815	Intermediate Similarity	NPD2346	Discontinued
0.7805	Intermediate Similarity	NPD3926	Phase 2
0.78	Intermediate Similarity	NPD7033	Discontinued
0.7778	Intermediate Similarity	NPD4628	Phase 3
0.7778	Intermediate Similarity	NPD2797	Approved
0.777	Intermediate Similarity	NPD943	Approved
0.7746	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7746	Intermediate Similarity	NPD422	Phase 1
0.7746	Intermediate Similarity	NPD1610	Phase 2
0.774	Intermediate Similarity	NPD6832	Phase 2
0.7738	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7727	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD9717	Approved
0.7682	Intermediate Similarity	NPD4308	Phase 3
0.767	Intermediate Similarity	NPD4361	Phase 2
0.767	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7662	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7625	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.76	Intermediate Similarity	NPD5124	Phase 1
0.76	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7597	Intermediate Similarity	NPD2654	Approved
0.7586	Intermediate Similarity	NPD3225	Approved
0.7568	Intermediate Similarity	NPD4625	Phase 3
0.7534	Intermediate Similarity	NPD3266	Approved
0.7534	Intermediate Similarity	NPD3267	Approved
0.7531	Intermediate Similarity	NPD1465	Phase 2
0.753	Intermediate Similarity	NPD5711	Approved
0.753	Intermediate Similarity	NPD5710	Approved
0.7517	Intermediate Similarity	NPD6798	Discontinued
0.75	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD4288	Approved
0.7484	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7471	Intermediate Similarity	NPD1729	Discontinued
0.7468	Intermediate Similarity	NPD1471	Phase 3
0.7451	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7448	Intermediate Similarity	NPD3972	Approved
0.7448	Intermediate Similarity	NPD1608	Approved
0.744	Intermediate Similarity	NPD2403	Approved
0.7432	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7425	Intermediate Similarity	NPD7229	Phase 3
0.7417	Intermediate Similarity	NPD4307	Phase 2
0.7417	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7417	Intermediate Similarity	NPD1613	Approved
0.74	Intermediate Similarity	NPD1296	Phase 2
0.7391	Intermediate Similarity	NPD7458	Discontinued
0.7379	Intermediate Similarity	NPD1201	Approved
0.7368	Intermediate Similarity	NPD447	Suspended
0.7368	Intermediate Similarity	NPD1933	Approved
0.7368	Intermediate Similarity	NPD230	Phase 1
0.7368	Intermediate Similarity	NPD6355	Discontinued
0.7358	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7355	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7353	Intermediate Similarity	NPD3751	Discontinued
0.7351	Intermediate Similarity	NPD6233	Phase 2
0.7351	Intermediate Similarity	NPD7584	Approved
0.7343	Intermediate Similarity	NPD9545	Approved
0.7337	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7325	Intermediate Similarity	NPD7003	Approved
0.7324	Intermediate Similarity	NPD9493	Approved
0.7321	Intermediate Similarity	NPD3787	Discontinued
0.7312	Intermediate Similarity	NPD5049	Phase 3
0.7308	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD4060	Phase 1
0.7301	Intermediate Similarity	NPD5889	Approved
0.7301	Intermediate Similarity	NPD5890	Approved
0.7297	Intermediate Similarity	NPD1470	Approved
0.7297	Intermediate Similarity	NPD1164	Approved
0.7296	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.729	Intermediate Similarity	NPD5406	Approved
0.729	Intermediate Similarity	NPD5408	Approved
0.729	Intermediate Similarity	NPD5405	Approved
0.729	Intermediate Similarity	NPD5404	Approved
0.7285	Intermediate Similarity	NPD411	Approved
0.7285	Intermediate Similarity	NPD3764	Approved
0.7284	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7279	Intermediate Similarity	NPD4749	Approved
0.7278	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD2354	Approved
0.7273	Intermediate Similarity	NPD8434	Phase 2
0.7273	Intermediate Similarity	NPD2296	Approved
0.7256	Intermediate Similarity	NPD6844	Discontinued
0.7248	Intermediate Similarity	NPD1019	Discontinued
0.7241	Intermediate Similarity	NPD17	Approved
0.7239	Intermediate Similarity	NPD6585	Discontinued
0.7234	Intermediate Similarity	NPD1241	Discontinued
0.7219	Intermediate Similarity	NPD3027	Phase 3
0.7213	Intermediate Similarity	NPD6777	Approved
0.7213	Intermediate Similarity	NPD6780	Approved
0.7213	Intermediate Similarity	NPD6776	Approved
0.7213	Intermediate Similarity	NPD6778	Approved
0.7213	Intermediate Similarity	NPD6779	Approved
0.7213	Intermediate Similarity	NPD6782	Approved
0.7213	Intermediate Similarity	NPD6781	Approved
0.7211	Intermediate Similarity	NPD1481	Phase 2
0.72	Intermediate Similarity	NPD8312	Approved
0.72	Intermediate Similarity	NPD8313	Approved
0.72	Intermediate Similarity	NPD2861	Phase 2
0.7197	Intermediate Similarity	NPD2424	Discontinued
0.7191	Intermediate Similarity	NPD4287	Approved
0.7184	Intermediate Similarity	NPD6104	Discontinued
0.7179	Intermediate Similarity	NPD4476	Approved
0.7179	Intermediate Similarity	NPD4477	Approved
0.7171	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD3887	Approved
0.716	Intermediate Similarity	NPD7199	Phase 2
0.7152	Intermediate Similarity	NPD1652	Phase 2
0.7151	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7447	Phase 1

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