NPASS Compound

Structure

CID223834 OpenBabel06191716022D 27 28 0 0 1 0 0 0 0 0999 V2000 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0000 -1.7321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 -1.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5000 -0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0000 -0.0000 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 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0000 1.7321 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 2.5000 -0.8660 0.0000 C 0 0 2 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 5.5000 0.8660 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 6.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.5000 -0.8660 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.5000 -0.8660 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 7.0000 1.7321 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.0000 -1.7321 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.0000 -1.7321 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 0.8660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.5000 0.8660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 10 1 0 0 0 0 3 18 1 0 0 0 0 4 18 1 0 0 0 0 5 6 1 0 0 0 0 5 11 1 0 0 0 0 6 19 1 0 0 0 0 7 10 2 0 0 0 0 7 12 1 0 0 0 0 8 12 1 0 0 0 0 8 18 1 0 0 0 0 9 20 1 0 0 0 0 10 19 1 0 0 0 0 11 2 1 6 0 0 0 11 26 1 0 0 0 0 12 21 2 0 0 0 0 13 9 1 6 0 0 0 13 14 1 0 0 0 0 13 27 1 0 0 0 0 14 15 1 0 0 0 0 14 22 1 1 0 0 0 15 16 1 0 0 0 0 15 23 1 6 0 0 0 16 17 1 0 0 0 0 16 24 1 1 0 0 0 17 26 1 6 0 0 0 17 27 1 0 0 0 0 18 19 1 0 0 0 0 19 25 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	904.23
Volume:	825.698
LogP:	0.685
LogD:	0.147
LogS:	-4.507
# Rotatable Bonds:	12
TPSA:	374.88
# H-Bond Aceptor:	23
# H-Bond Donor:	13
# Rings:	7
# Heavy Atoms:	23

MedChem Properties

QED Drug-Likeness Score:	0.044
Synthetic Accessibility Score:	5.725
Fsp3:	0.415
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	2
Golden Triangle Rule:	Rejected
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.667
MDCK Permeability:	3.692235259222798e-05
Pgp-inhibitor:	0.006
Pgp-substrate:	0.997
Human Intestinal Absorption (HIA):	0.928
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.075
Plasma Protein Binding (PPB):	91.99186706542969%
Volume Distribution (VD):	0.587
Pgp-substrate:	15.610790252685547%

ADMET: Metabolism

CYP1A2-inhibitor:	0.071
CYP1A2-substrate:	0.01
CYP2C19-inhibitor:	0.025
CYP2C19-substrate:	0.042
CYP2C9-inhibitor:	0.04
CYP2C9-substrate:	0.058
CYP2D6-inhibitor:	0.036
CYP2D6-substrate:	0.114
CYP3A4-inhibitor:	0.032
CYP3A4-substrate:	0.002

ADMET: Excretion

Clearance (CL):	0.91
Half-life (T1/2):	0.758

ADMET: Toxicity

hERG Blockers:	0.197
Human Hepatotoxicity (H-HT):	0.12
Drug-inuced Liver Injury (DILI):	0.984
AMES Toxicity:	0.722
Rat Oral Acute Toxicity:	0.024
Maximum Recommended Daily Dose:	0.003
Skin Sensitization:	0.953
Carcinogencity:	0.079
Eye Corrosion:	0.003
Eye Irritation:	0.151
Respiratory Toxicity:	0.008

Download Data

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

Natural Product: NPC223834

Natural Product ID:	NPC223834
*Common Name:**	Dihydrovomifoliol-O-Beta-D-Glucopyranoside
IUPAC Name:	(4S)-4-hydroxy-3,5,5-trimethyl-4-[(3R)-3-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxybutyl]cyclohex-2-en-1-one
Synonyms:
Standard InCHIKey:	CZYPGTRKJFYXLT-SUHXYMONSA-N
Standard InCHI:	InChI=1S/C19H32O8/c1-10-7-12(21)8-18(3,4)19(10,25)6-5-11(2)26-17-16(24)15(23)14(22)13(9-20)27-17/h7,11,13-17,20,22-25H,5-6,8-9H2,1-4H3/t11-,13-,14-,15+,16-,17-,19-/m1/s1
SMILES:	OC[C@H]1O[C@@H](O[C@@H](CC[C@@]2(O)C(=CC(=O)CC2(C)C)C)C)[C@@H]([C@H]([C@@H]1O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3326713
PubChem CID:	14135399
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0003909] Fatty Acyls [CHEMONTID:0001766] Fatty acyl glycosides [CHEMONTID:0003861] Fatty acyl glycosides of mono- and disaccharides

*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
NPO19369	Bacillus thuringiensis	Species	Bacillaceae	Bacteria	n.a.	n.a.	n.a.	PMID[11087590]
NPO6836	Alpinia blepharocalyx	Species	Zingiberaceae	Eukaryota	seeds	Mengha, Yunnan Province, China	1991-Aug	PMID[11277741]
NPO6836	Alpinia blepharocalyx	Species	Zingiberaceae	Eukaryota	seeds	n.a.	n.a.	PMID[11325233]
NPO11884	Macaranga tanarius	Species	Euphorbiaceae	Eukaryota	n.a.	leaf	n.a.	PMID[11421757]
NPO6836	Alpinia blepharocalyx	Species	Zingiberaceae	Eukaryota	Seeds	n.a.	n.a.	PMID[11430002]
NPO23577	Wolfiporia cocos	Species	Coriolaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11975480]
NPO3261	Aplysina archeri	Species	Aplysinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[1324982]
NPO6457	Pinus strobus	Species	Pinaceae	Eukaryota	n.a.	heartwood	n.a.	PMID[13465274]
NPO17593	Pinus sylvestris	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[1536925]
NPO10729	Lechevalieria aerocolonigenes	Species	Pseudonocardiaceae	Bacteria	n.a.	n.a.	n.a.	PMID[15620255]
NPO11884	Macaranga tanarius	Species	Euphorbiaceae	Eukaryota	n.a.	leaf	n.a.	PMID[15974621]
NPO11884	Macaranga tanarius	Species	Euphorbiaceae	Eukaryota	leaves	Krachong waterfall area, Trang Province, Thailand	2001-APR	PMID[15974621]
NPO14054	Penicillium janczewskii	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16180822]
NPO3453	Elaeocarpus fuscoides	Species	Elaeocarpaceae	Eukaryota	leaves	n.a.	n.a.	PMID[17451272]
NPO422	Euphorbia cornigera	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17512094]
NPO11884	Macaranga tanarius	Species	Euphorbiaceae	Eukaryota	n.a.	leaf	n.a.	PMID[18844422]
NPO11884	Macaranga tanarius	Species	Euphorbiaceae	Eukaryota	leaves	n.a.	n.a.	PMID[18844422]
NPO422	Euphorbia cornigera	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19376614]
NPO23577	Wolfiporia cocos	Species	Coriolaceae	Eukaryota	epidermis of the sclerotia	n.a.	n.a.	PMID[19746919]
NPO6648	Piper retrofractum	Species	Piperaceae	Eukaryota	Fruits	n.a.	n.a.	PMID[23506561]
NPO17593	Pinus sylvestris	Species	Pinaceae	Eukaryota	n.a.	seed	n.a.	PMID[24225786]
NPO6648	Piper retrofractum	Species	Piperaceae	Eukaryota	leaves	n.a.	n.a.	PMID[25127165]
NPO23577	Wolfiporia cocos	Species	Coriolaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27808511]
NPO11884	Macaranga tanarius	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[28972755]
NPO2697	Monodora tenuifolia	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[3509958]
NPO23577	Wolfiporia cocos	Species	Coriolaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8984162]
NPO6836	Alpinia blepharocalyx	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9461664]
NPO11884	Macaranga tanarius	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO6836	Alpinia blepharocalyx	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO4564	Anguilla japonica	Species	Anguillidae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO17593	Pinus sylvestris	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO24089	Alcea rosea	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6836	Alpinia blepharocalyx	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1209	Swartzia madagascariensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8543	Meconopsis horridula	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23577	Wolfiporia cocos	Species	Coriolaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11884	Macaranga tanarius	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2408	Millettia laurentii	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4564	Anguilla japonica	Species	Anguillidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17593	Pinus sylvestris	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1581	Passiflora caerulea	Species	Passifloraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6648	Piper retrofractum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11884	Macaranga tanarius	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO17593	Pinus sylvestris	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO23577	Wolfiporia cocos	Species	Coriolaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO24089	Alcea rosea	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO7449	Eleutherobia albiflora	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3956	Maesa ramentacea	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8058	Pluchea odorata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7606	Salacia lehmbachii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12330	Pseudophryne coriacea	Species	Myobatrachidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1209	Swartzia madagascariensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7007	Eucalyptus jenseni	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3453	Elaeocarpus fuscoides	Species	Elaeocarpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1390	Melolontha melolontha	Species	Scarabaeidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO305	Vitex pinnata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4564	Anguilla japonica	Species	Anguillidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO422	Euphorbia cornigera	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25760	Aspergillus striatus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO477	Lepraria xanthina	Species	Stereocaulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5261	Sideroxylon cubense	Species	Sapotaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7760	Macrolepiota neomastoidea	Species	Agaricaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO849	Euonymus tingens	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5508	Stevia purpurea	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11884	Macaranga tanarius	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2250	Hylocomium splendens	Species	Hylocomiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11747	Ocimum tenuiflorum	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15164	Jacobaea adonidifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7087	Oxera splendida	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8543	Meconopsis horridula	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2697	Monodora tenuifolia	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5584	Aldisa sanguinea	Species	Dorididae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6457	Pinus strobus	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO295	Kokoona reflexa	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3280	Penicillium crustaceum	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO896	Streptomyces kanamyceticus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO4274	Alcyonium utinomii	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3261	Aplysina archeri	Species	Aplysinidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10729	Lechevalieria aerocolonigenes	Species	Pseudonocardiaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO6836	Alpinia blepharocalyx	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3408	Viguiera decurrens	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5975	Aspergillus carneus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19369	Bacillus thuringiensis	Species	Bacillaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO1242	Balanops australiana	Species	Balanopaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1489	Pseudoplexaura flagellosa	Species	Plexauridae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18993	Araiostegiella perdurans	Species	Davalliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17593	Pinus sylvestris	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24089	Alcea rosea	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23577	Wolfiporia cocos	Species	Coriolaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14054	Penicillium janczewskii	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2408	Millettia laurentii	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3554	Aonidiella aurantii	Species	Diaspididae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15487	Gymnopus confluens	Species	Omphalotaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2993	0totodarus sloanii	Species	Ommastrephidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5344	Calodendrum capense	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6648	Piper retrofractum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4949	Salvia yosgadensis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6231	Cortinarius odoratus	Species	Cortinariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6330	Croton caudatus	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1581	Passiflora caerulea	Species	Passifloraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3743	Sideritis brevibracteata	Species	Lamiaceae	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
Others	6

Activity Type	# Activity
Individual Protein	1
Others	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT60	Individual Protein	Lysosomal alpha-glucosidase	Homo sapiens	Inhibition	=	6.9	%	PMID[522761]
NPT35	Others	n.a.		Activity	=	0.12	uM	PMID[522761]
NPT35	Others	n.a.		Activity	=	0.92	uM	PMID[522761]
NPT35	Others	n.a.		Activity	=	0.21	uM	PMID[522761]
NPT35	Others	n.a.		Activity	=	0.34	uM	PMID[522761]
NPT35	Others	n.a.		Activity	=	20.5	%	PMID[522761]

☑ 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 NPC223834 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	199
0.1-0.2	1201
0.2-0.3	4332
0.3-0.4	7703
0.4-0.5	13916
0.5-0.6	7449
0.6-0.7	6586
0.7-0.8	1257
0.8-0.85	38
0.85-0.9	9
0.9-0.95	6
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9167	High Similarity	NPC474194
0.9158	High Similarity	NPC108141
0.9072	High Similarity	NPC56071
0.9072	High Similarity	NPC307517
0.9072	High Similarity	NPC81483
0.9072	High Similarity	NPC70733
0.9072	High Similarity	NPC169468
0.9072	High Similarity	NPC61630
0.89	High Similarity	NPC151516
0.8889	High Similarity	NPC154127
0.8704	High Similarity	NPC234522
0.8586	High Similarity	NPC278506
0.8585	High Similarity	NPC174836
0.8558	High Similarity	NPC473288
0.8545	High Similarity	NPC48692
0.85	High Similarity	NPC198422
0.85	High Similarity	NPC40182
0.8485	Intermediate Similarity	NPC256230
0.8469	Intermediate Similarity	NPC2003
0.8469	Intermediate Similarity	NPC25701
0.8426	Intermediate Similarity	NPC181145
0.8396	Intermediate Similarity	NPC83005
0.8393	Intermediate Similarity	NPC28532
0.8381	Intermediate Similarity	NPC177524
0.8381	Intermediate Similarity	NPC219900
0.8381	Intermediate Similarity	NPC392
0.8381	Intermediate Similarity	NPC272576
0.8333	Intermediate Similarity	NPC311592
0.8333	Intermediate Similarity	NPC75167
0.83	Intermediate Similarity	NPC143446
0.8286	Intermediate Similarity	NPC293512
0.8269	Intermediate Similarity	NPC470104
0.8265	Intermediate Similarity	NPC302584
0.8252	Intermediate Similarity	NPC150463
0.8252	Intermediate Similarity	NPC214277
0.8241	Intermediate Similarity	NPC471967
0.8224	Intermediate Similarity	NPC154856
0.8224	Intermediate Similarity	NPC46407
0.8224	Intermediate Similarity	NPC52241
0.8224	Intermediate Similarity	NPC235014
0.8224	Intermediate Similarity	NPC475317
0.8165	Intermediate Similarity	NPC62696
0.8165	Intermediate Similarity	NPC260665
0.8165	Intermediate Similarity	NPC477944
0.8165	Intermediate Similarity	NPC293038
0.8144	Intermediate Similarity	NPC471755
0.8144	Intermediate Similarity	NPC471756
0.8142	Intermediate Similarity	NPC202051
0.8131	Intermediate Similarity	NPC246205
0.8119	Intermediate Similarity	NPC90583
0.8095	Intermediate Similarity	NPC100955
0.8095	Intermediate Similarity	NPC121566
0.8091	Intermediate Similarity	NPC220293
0.8091	Intermediate Similarity	NPC74727
0.8091	Intermediate Similarity	NPC102088
0.8081	Intermediate Similarity	NPC475441
0.8081	Intermediate Similarity	NPC472197
0.8077	Intermediate Similarity	NPC476126
0.8077	Intermediate Similarity	NPC476235
0.8073	Intermediate Similarity	NPC210420
0.8073	Intermediate Similarity	NPC37739
0.8073	Intermediate Similarity	NPC46388
0.8073	Intermediate Similarity	NPC474265
0.8073	Intermediate Similarity	NPC130427
0.8039	Intermediate Similarity	NPC240372
0.8036	Intermediate Similarity	NPC45475
0.8019	Intermediate Similarity	NPC63023
0.8019	Intermediate Similarity	NPC95243
0.8	Intermediate Similarity	NPC189884
0.8	Intermediate Similarity	NPC474410
0.8	Intermediate Similarity	NPC293658
0.8	Intermediate Similarity	NPC264153
0.8	Intermediate Similarity	NPC138334
0.8	Intermediate Similarity	NPC47063
0.8	Intermediate Similarity	NPC320089
0.8	Intermediate Similarity	NPC269315
0.8	Intermediate Similarity	NPC271138
0.8	Intermediate Similarity	NPC204458
0.7982	Intermediate Similarity	NPC191763
0.7981	Intermediate Similarity	NPC476213
0.7981	Intermediate Similarity	NPC477870
0.7981	Intermediate Similarity	NPC477871
0.7981	Intermediate Similarity	NPC476246
0.7981	Intermediate Similarity	NPC97435
0.7981	Intermediate Similarity	NPC280991
0.7963	Intermediate Similarity	NPC57362
0.7963	Intermediate Similarity	NPC204407
0.7963	Intermediate Similarity	NPC306746
0.7963	Intermediate Similarity	NPC237503
0.7963	Intermediate Similarity	NPC167383
0.7963	Intermediate Similarity	NPC137917
0.7949	Intermediate Similarity	NPC152091
0.7946	Intermediate Similarity	NPC474483
0.7946	Intermediate Similarity	NPC471547
0.7946	Intermediate Similarity	NPC23046
0.7946	Intermediate Similarity	NPC309433
0.7944	Intermediate Similarity	NPC143609
0.7928	Intermediate Similarity	NPC473882
0.7928	Intermediate Similarity	NPC165439
0.7928	Intermediate Similarity	NPC474557
0.7928	Intermediate Similarity	NPC472274
0.7928	Intermediate Similarity	NPC475163
0.7928	Intermediate Similarity	NPC477580
0.7925	Intermediate Similarity	NPC470768
0.7909	Intermediate Similarity	NPC116794
0.7909	Intermediate Similarity	NPC256798
0.7909	Intermediate Similarity	NPC128925
0.7905	Intermediate Similarity	NPC201191
0.7895	Intermediate Similarity	NPC473130
0.7895	Intermediate Similarity	NPC268184
0.789	Intermediate Similarity	NPC199457
0.789	Intermediate Similarity	NPC476885
0.789	Intermediate Similarity	NPC476882
0.789	Intermediate Similarity	NPC474589
0.789	Intermediate Similarity	NPC78046
0.789	Intermediate Similarity	NPC68419
0.789	Intermediate Similarity	NPC220984
0.789	Intermediate Similarity	NPC476883
0.789	Intermediate Similarity	NPC270667
0.789	Intermediate Similarity	NPC110139
0.789	Intermediate Similarity	NPC274507
0.789	Intermediate Similarity	NPC29069
0.789	Intermediate Similarity	NPC75747
0.789	Intermediate Similarity	NPC127056
0.789	Intermediate Similarity	NPC476881
0.789	Intermediate Similarity	NPC174679
0.789	Intermediate Similarity	NPC476886
0.789	Intermediate Similarity	NPC279554
0.789	Intermediate Similarity	NPC90856
0.789	Intermediate Similarity	NPC164194
0.789	Intermediate Similarity	NPC59804
0.789	Intermediate Similarity	NPC102914
0.789	Intermediate Similarity	NPC476880
0.789	Intermediate Similarity	NPC476887
0.789	Intermediate Similarity	NPC7870
0.789	Intermediate Similarity	NPC129340
0.789	Intermediate Similarity	NPC136877
0.789	Intermediate Similarity	NPC476884
0.789	Intermediate Similarity	NPC27551
0.789	Intermediate Similarity	NPC108709
0.789	Intermediate Similarity	NPC56713
0.789	Intermediate Similarity	NPC475296
0.789	Intermediate Similarity	NPC269095
0.789	Intermediate Similarity	NPC114961
0.7885	Intermediate Similarity	NPC64348
0.7876	Intermediate Similarity	NPC473828
0.7876	Intermediate Similarity	NPC473617
0.7876	Intermediate Similarity	NPC176005
0.787	Intermediate Similarity	NPC476123
0.787	Intermediate Similarity	NPC177246
0.787	Intermediate Similarity	NPC151393
0.787	Intermediate Similarity	NPC28198
0.787	Intermediate Similarity	NPC94942
0.787	Intermediate Similarity	NPC284807
0.7864	Intermediate Similarity	NPC266842
0.7864	Intermediate Similarity	NPC91197
0.7864	Intermediate Similarity	NPC309503
0.7864	Intermediate Similarity	NPC96597
0.7864	Intermediate Similarity	NPC125551
0.7864	Intermediate Similarity	NPC155319
0.7864	Intermediate Similarity	NPC124246
0.7864	Intermediate Similarity	NPC239547
0.7863	Intermediate Similarity	NPC297950
0.7863	Intermediate Similarity	NPC222307
0.7857	Intermediate Similarity	NPC58448
0.7857	Intermediate Similarity	NPC160415
0.7857	Intermediate Similarity	NPC31797
0.7857	Intermediate Similarity	NPC279638
0.7857	Intermediate Similarity	NPC471816
0.785	Intermediate Similarity	NPC210178
0.785	Intermediate Similarity	NPC470763
0.785	Intermediate Similarity	NPC111952
0.785	Intermediate Similarity	NPC162033
0.785	Intermediate Similarity	NPC470767
0.785	Intermediate Similarity	NPC239961
0.7838	Intermediate Similarity	NPC200944
0.7838	Intermediate Similarity	NPC73455
0.7838	Intermediate Similarity	NPC473159
0.7838	Intermediate Similarity	NPC178981
0.7833	Intermediate Similarity	NPC231240
0.783	Intermediate Similarity	NPC99266
0.783	Intermediate Similarity	NPC8196
0.783	Intermediate Similarity	NPC478057
0.7826	Intermediate Similarity	NPC170084
0.7826	Intermediate Similarity	NPC476204
0.7826	Intermediate Similarity	NPC42675
0.7822	Intermediate Similarity	NPC91654
0.7822	Intermediate Similarity	NPC67398
0.7822	Intermediate Similarity	NPC474792
0.7818	Intermediate Similarity	NPC179434
0.7818	Intermediate Similarity	NPC211798
0.7818	Intermediate Similarity	NPC285410
0.7818	Intermediate Similarity	NPC297208
0.7818	Intermediate Similarity	NPC164419
0.7818	Intermediate Similarity	NPC250481
0.7818	Intermediate Similarity	NPC108748
0.7818	Intermediate Similarity	NPC235841
0.7818	Intermediate Similarity	NPC30397
0.7818	Intermediate Similarity	NPC473481
0.7818	Intermediate Similarity	NPC263827

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 NPC223834 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	177
0.1-0.2	1637
0.2-0.3	3797
0.3-0.4	2289
0.4-0.5	770
0.5-0.6	295
0.6-0.7	178
0.7-0.8	7
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8381	Intermediate Similarity	NPD6686	Approved
0.8286	Intermediate Similarity	NPD6412	Phase 2
0.7798	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD8328	Phase 3
0.7563	Intermediate Similarity	NPD7507	Approved
0.7451	Intermediate Similarity	NPD6698	Approved
0.7451	Intermediate Similarity	NPD46	Approved
0.7377	Intermediate Similarity	NPD7319	Approved
0.7311	Intermediate Similarity	NPD6370	Approved
0.729	Intermediate Similarity	NPD8029	Clinical (unspecified phase)
0.7265	Intermediate Similarity	NPD7328	Approved
0.7265	Intermediate Similarity	NPD7327	Approved
0.7227	Intermediate Similarity	NPD8513	Phase 3
0.7227	Intermediate Similarity	NPD8516	Approved
0.7227	Intermediate Similarity	NPD8515	Approved
0.7227	Intermediate Similarity	NPD7503	Approved
0.7227	Intermediate Similarity	NPD8517	Approved
0.7203	Intermediate Similarity	NPD7516	Approved
0.7193	Intermediate Similarity	NPD8413	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6054	Approved
0.7143	Intermediate Similarity	NPD6059	Approved
0.7143	Intermediate Similarity	NPD8377	Approved
0.7143	Intermediate Similarity	NPD8294	Approved
0.7105	Intermediate Similarity	NPD6371	Approved
0.7083	Intermediate Similarity	NPD8378	Approved
0.7083	Intermediate Similarity	NPD8335	Approved
0.7083	Intermediate Similarity	NPD8380	Approved
0.7083	Intermediate Similarity	NPD8296	Approved
0.7083	Intermediate Similarity	NPD8033	Approved
0.7083	Intermediate Similarity	NPD8379	Approved
0.7073	Intermediate Similarity	NPD8293	Discontinued
0.7069	Intermediate Similarity	NPD8133	Approved
0.7034	Intermediate Similarity	NPD7115	Discovery
0.7018	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7016	Intermediate Similarity	NPD7736	Approved
0.6983	Remote Similarity	NPD6882	Approved
0.6972	Remote Similarity	NPD4225	Approved
0.6967	Remote Similarity	NPD6067	Discontinued
0.6957	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6942	Remote Similarity	NPD6016	Approved
0.6942	Remote Similarity	NPD6015	Approved
0.6916	Remote Similarity	NPD5282	Discontinued
0.6911	Remote Similarity	NPD7492	Approved
0.6909	Remote Similarity	NPD7640	Approved
0.6909	Remote Similarity	NPD7639	Approved
0.6891	Remote Similarity	NPD6009	Approved
0.6887	Remote Similarity	NPD7983	Approved
0.6885	Remote Similarity	NPD5988	Approved
0.6881	Remote Similarity	NPD7902	Approved
0.687	Remote Similarity	NPD6373	Approved
0.687	Remote Similarity	NPD6372	Approved
0.6863	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.686	Remote Similarity	NPD6319	Approved
0.6855	Remote Similarity	NPD6616	Approved
0.6838	Remote Similarity	NPD8297	Approved
0.6822	Remote Similarity	NPD5779	Approved
0.6822	Remote Similarity	NPD5778	Approved
0.6818	Remote Similarity	NPD7638	Approved
0.68	Remote Similarity	NPD7078	Approved
0.6783	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.678	Remote Similarity	NPD4632	Approved
0.6765	Remote Similarity	NPD6110	Phase 1
0.6759	Remote Similarity	NPD7748	Approved
0.6754	Remote Similarity	NPD7128	Approved
0.6754	Remote Similarity	NPD5739	Approved
0.6754	Remote Similarity	NPD6675	Approved
0.6754	Remote Similarity	NPD6402	Approved
0.6752	Remote Similarity	NPD6649	Approved
0.6752	Remote Similarity	NPD6650	Approved
0.6731	Remote Similarity	NPD3618	Phase 1
0.6729	Remote Similarity	NPD7515	Phase 2
0.6727	Remote Similarity	NPD6084	Phase 2
0.6727	Remote Similarity	NPD6083	Phase 2
0.6696	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6696	Remote Similarity	NPD5344	Discontinued
0.6696	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6694	Remote Similarity	NPD7641	Discontinued
0.6667	Remote Similarity	NPD6399	Phase 3
0.6667	Remote Similarity	NPD8074	Phase 3
0.664	Remote Similarity	NPD8342	Approved
0.664	Remote Similarity	NPD8299	Approved
0.664	Remote Similarity	NPD8341	Approved
0.664	Remote Similarity	NPD8340	Approved
0.6638	Remote Similarity	NPD7320	Approved
0.6638	Remote Similarity	NPD6881	Approved
0.6638	Remote Similarity	NPD6899	Approved
0.6637	Remote Similarity	NPD5211	Phase 2
0.6636	Remote Similarity	NPD7838	Discovery
0.6614	Remote Similarity	NPD6033	Approved
0.6606	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6606	Remote Similarity	NPD7900	Approved
0.6577	Remote Similarity	NPD4755	Approved
0.6574	Remote Similarity	NPD6411	Approved
0.656	Remote Similarity	NPD7642	Approved
0.6555	Remote Similarity	NPD6053	Discontinued
0.6552	Remote Similarity	NPD5697	Approved
0.6552	Remote Similarity	NPD5701	Approved
0.6545	Remote Similarity	NPD5695	Phase 3
0.6542	Remote Similarity	NPD5328	Approved
0.6542	Remote Similarity	NPD4753	Phase 2
0.6538	Remote Similarity	NPD3666	Approved
0.6538	Remote Similarity	NPD3133	Approved
0.6538	Remote Similarity	NPD3665	Phase 1
0.6525	Remote Similarity	NPD6883	Approved
0.6525	Remote Similarity	NPD4634	Approved
0.6525	Remote Similarity	NPD7290	Approved
0.6525	Remote Similarity	NPD7102	Approved
0.6522	Remote Similarity	NPD5141	Approved
0.6518	Remote Similarity	NPD5696	Approved
0.6514	Remote Similarity	NPD4202	Approved
0.6512	Remote Similarity	NPD6914	Discontinued
0.6509	Remote Similarity	NPD7524	Approved
0.6486	Remote Similarity	NPD7839	Suspended
0.6471	Remote Similarity	NPD6869	Approved
0.6471	Remote Similarity	NPD6617	Approved
0.6471	Remote Similarity	NPD6847	Approved
0.6471	Remote Similarity	NPD8130	Phase 1
0.6466	Remote Similarity	NPD6008	Approved
0.6462	Remote Similarity	NPD7260	Phase 2
0.646	Remote Similarity	NPD4696	Approved
0.646	Remote Similarity	NPD5285	Approved
0.646	Remote Similarity	NPD4700	Approved
0.646	Remote Similarity	NPD5286	Approved
0.6457	Remote Similarity	NPD8451	Approved
0.6441	Remote Similarity	NPD6014	Approved
0.6441	Remote Similarity	NPD6013	Approved
0.6441	Remote Similarity	NPD6012	Approved
0.6429	Remote Similarity	NPD7830	Approved
0.6429	Remote Similarity	NPD7604	Phase 2
0.6429	Remote Similarity	NPD7829	Approved
0.6422	Remote Similarity	NPD6079	Approved
0.6415	Remote Similarity	NPD7521	Approved
0.6415	Remote Similarity	NPD7146	Approved
0.6415	Remote Similarity	NPD5330	Approved
0.6415	Remote Similarity	NPD6684	Approved
0.6415	Remote Similarity	NPD4623	Approved
0.6415	Remote Similarity	NPD4519	Discontinued
0.6415	Remote Similarity	NPD7334	Approved
0.6415	Remote Similarity	NPD5279	Phase 3
0.6415	Remote Similarity	NPD6409	Approved
0.6406	Remote Similarity	NPD8448	Approved
0.64	Remote Similarity	NPD5983	Phase 2
0.6396	Remote Similarity	NPD5210	Approved
0.6396	Remote Similarity	NPD4629	Approved
0.6389	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6389	Remote Similarity	NPD6101	Approved
0.6385	Remote Similarity	NPD5956	Approved
0.6381	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6381	Remote Similarity	NPD4786	Approved
0.6356	Remote Similarity	NPD6011	Approved
0.6349	Remote Similarity	NPD8080	Discontinued
0.6348	Remote Similarity	NPD7632	Discontinued
0.6348	Remote Similarity	NPD4633	Approved
0.6348	Remote Similarity	NPD5224	Approved
0.6348	Remote Similarity	NPD5225	Approved
0.6348	Remote Similarity	NPD5226	Approved
0.6346	Remote Similarity	NPD3667	Approved
0.6346	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6339	Remote Similarity	NPD4697	Phase 3
0.6333	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.633	Remote Similarity	NPD5785	Approved
0.6328	Remote Similarity	NPD6336	Discontinued
0.6325	Remote Similarity	NPD4767	Approved
0.6325	Remote Similarity	NPD4768	Approved
0.6321	Remote Similarity	NPD1694	Approved
0.6316	Remote Similarity	NPD6648	Approved
0.6311	Remote Similarity	NPD4695	Discontinued
0.6296	Remote Similarity	NPD6672	Approved
0.6296	Remote Similarity	NPD6903	Approved
0.6296	Remote Similarity	NPD5737	Approved
0.6296	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6293	Remote Similarity	NPD5174	Approved
0.6293	Remote Similarity	NPD5175	Approved
0.6286	Remote Similarity	NPD6695	Phase 3
0.6275	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6273	Remote Similarity	NPD5281	Approved
0.6273	Remote Similarity	NPD7637	Suspended
0.6273	Remote Similarity	NPD5284	Approved
0.627	Remote Similarity	NPD8444	Approved
0.627	Remote Similarity	NPD6921	Approved
0.6262	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6261	Remote Similarity	NPD5223	Approved
0.626	Remote Similarity	NPD8390	Approved
0.626	Remote Similarity	NPD8391	Approved
0.626	Remote Similarity	NPD8392	Approved
0.625	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.625	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6239	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6231	Remote Similarity	NPD8337	Approved
0.6231	Remote Similarity	NPD8336	Approved
0.6222	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6218	Remote Similarity	NPD4730	Approved
0.6218	Remote Similarity	NPD4729	Approved
0.621	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.6204	Remote Similarity	NPD3573	Approved
0.6195	Remote Similarity	NPD5221	Approved
0.6195	Remote Similarity	NPD5222	Approved
0.6195	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.619	Remote Similarity	NPD4223	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