NPASS Compound

Structure

CID106446 OpenBabel06191715452D 30 34 0 0 1 0 0 0 0 0999 V2000 -3.7781 4.0441 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9975 0.6045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8440 1.7872 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7950 -1.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7461 1.1691 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 -4.5871 3.4563 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5871 2.4563 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0029 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.0519 -0.8090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.5382 2.1473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.0519 0.8090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 -2.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.5382 3.7653 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.0029 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.4641 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 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 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 -5.8472 4.7164 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.1260 2.9563 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 8 1 0 0 0 0 3 9 1 0 0 0 0 3 14 1 0 0 0 0 4 10 1 0 0 0 0 4 11 1 0 0 0 0 5 12 2 0 0 0 0 5 20 1 0 0 0 0 6 22 1 0 0 0 0 7 21 1 0 0 0 0 7 28 1 0 0 0 0 8 9 2 0 0 0 0 8 18 1 0 0 0 0 9 12 1 0 0 0 0 10 11 1 0 0 0 0 10 20 1 1 0 0 0 11 21 1 1 0 0 0 12 29 1 0 0 0 0 13 6 1 6 0 0 0 13 15 1 0 0 0 0 13 30 1 0 0 0 0 14 20 1 1 0 0 0 14 21 1 0 0 0 0 15 16 1 0 0 0 0 15 23 1 1 0 0 0 16 17 1 0 0 0 0 16 24 1 6 0 0 0 17 19 1 0 0 0 0 17 25 1 1 0 0 0 18 26 2 0 0 0 0 18 29 1 0 0 0 0 19 28 1 6 0 0 0 19 30 1 0 0 0 0 20 2 1 1 0 0 0 21 27 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	424.17
Volume:	400.193
LogP:	-0.295
LogD:	-0.088
LogS:	-2.043
# Rotatable Bonds:	4
TPSA:	152.98
# H-Bond Aceptor:	9
# H-Bond Donor:	6
# Rings:	5
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.313
Synthetic Accessibility Score:	5.572
Fsp3:	0.714
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.278
MDCK Permeability:	2.7977186618954875e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.968
Human Intestinal Absorption (HIA):	0.87
20% Bioavailability (F20%):	0.03
30% Bioavailability (F30%):	0.891

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.114
Plasma Protein Binding (PPB):	72.38114166259766%
Volume Distribution (VD):	0.668
Pgp-substrate:	24.55860137939453%

ADMET: Metabolism

CYP1A2-inhibitor:	0.025
CYP1A2-substrate:	0.387
CYP2C19-inhibitor:	0.009
CYP2C19-substrate:	0.167
CYP2C9-inhibitor:	0.002
CYP2C9-substrate:	0.058
CYP2D6-inhibitor:	0.001
CYP2D6-substrate:	0.106
CYP3A4-inhibitor:	0.06
CYP3A4-substrate:	0.057

ADMET: Excretion

Clearance (CL):	1.304
Half-life (T1/2):	0.809

ADMET: Toxicity

hERG Blockers:	0.09
Human Hepatotoxicity (H-HT):	0.557
Drug-inuced Liver Injury (DILI):	0.474
AMES Toxicity:	0.382
Rat Oral Acute Toxicity:	0.666
Maximum Recommended Daily Dose:	0.156
Skin Sensitization:	0.401
Carcinogencity:	0.102
Eye Corrosion:	0.003
Eye Irritation:	0.026
Respiratory Toxicity:	0.959

Download Data

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

Natural Product: NPC106446

Natural Product ID:	NPC106446
*Common Name:**	Chloranoside A
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	HCKVSBCCVCMKKB-NGHDLRGFSA-N
Standard InCHI:	InChI=1S/C21H28O9/c1-8-9-3-14-20(2,5-12(9)29-18(8)26)10-4-11(10)21(14,27)7-28-19-17(25)16(24)15(23)13(6-22)30-19/h5,10-11,13-17,19,22-25,27H,3-4,6-7H2,1-2H3/t10-,11+,13-,14-,15-,16+,17-,19-,20+,21-/m1/s1
SMILES:	OC[C@H]1O[C@@H](OC[C@@]2(O)[C@H]3C[C@H]3[C@]3([C@H]2CC2=C(C)C(=O)OC2=C3)C)[C@@H]([C@H]([C@@H]1O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL480072
PubChem CID:	11962123
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001634] Naphthofurans

*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
NPO2300	Actinidia deliciosa	Species	Actinidiaceae	Eukaryota	Fruits	Spanish		DOI[10.1021/jf00010a019]
NPO2300	Actinidia deliciosa	Species	Actinidiaceae	Eukaryota	Fruits	n.a.		DOI[10.1021/jf00016a013]
NPO2300	Actinidia deliciosa	Species	Actinidiaceae	Eukaryota	n.a.	Germany		DOI[10.1021/jf00016a013]
NPO2300	Actinidia deliciosa	Species	Actinidiaceae	Eukaryota	n.a.	Italy		DOI[10.1021/jf00016a013]
NPO2300	Actinidia deliciosa	Species	Actinidiaceae	Eukaryota	Fruits	Turkey		DOI[10.1111/j.1745-4557.2003.tb00250.x]
NPO2300	Actinidia deliciosa	Species	Actinidiaceae	Eukaryota	Fruits	n.a.		DOI[10.17660/ActaHortic.2003.610.16]
NPO2300	Actinidia deliciosa	Species	Actinidiaceae	Eukaryota	Fruits	n.a.		PMID[10794642]
NPO2300	Actinidia deliciosa	Species	Actinidiaceae	Eukaryota	Fruits	n.a.		PMID[10820090]
NPO2300	Actinidia deliciosa	Species	Actinidiaceae	Eukaryota	Fruits	n.a.		PMID[11754554]
NPO2300	Actinidia deliciosa	Species	Actinidiaceae	Eukaryota	Fruits	n.a.		PMID[15315387]
NPO2300	Actinidia deliciosa	Species	Actinidiaceae	Eukaryota	Fruits	n.a.		PMID[16076125]
NPO29221	Sarcandra glabra	Species	Chloranthaceae	Eukaryota	Whole plant	n.a.	n.a.	PMID[16643038]
NPO2300	Actinidia deliciosa	Species	Actinidiaceae	Eukaryota	Fruits	n.a.		PMID[16920856]
NPO2300	Actinidia deliciosa	Species	Actinidiaceae	Eukaryota	Fruits	n.a.		PMID[19358604]
NPO29221	Sarcandra glabra	Species	Chloranthaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20038159]
NPO2300	Actinidia deliciosa	Species	Actinidiaceae	Eukaryota	Fruits	n.a.		PMID[21190690]
NPO6674	Burkholderia ambifaria	Species	Burkholderiaceae	Bacteria	n.a.	n.a.	n.a.	PMID[22988812]
NPO2300	Actinidia deliciosa	Species	Actinidiaceae	Eukaryota	Fruits	n.a.		PMID[23394984]
NPO2300	Actinidia deliciosa	Species	Actinidiaceae	Eukaryota	n.a.	Germany		PMID[23394984]
NPO2300	Actinidia deliciosa	Species	Actinidiaceae	Eukaryota	n.a.	New Zealand		PMID[23394984]
NPO2300	Actinidia deliciosa	Species	Actinidiaceae	Eukaryota	Fruits	n.a.		PMID[2413754]
NPO17386	Securidaca longepedunculata	Species	Polygalaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24216090]
NPO29221	Sarcandra glabra	Species	Chloranthaceae	Eukaryota	aerial part	n.a.	n.a.	PMID[25442304]
NPO11257	Momordica dioica	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[30673219]
NPO2300	Actinidia deliciosa	Species	Actinidiaceae	Eukaryota	Fruits	n.a.		PMID[9542132]
NPO29221	Sarcandra glabra	Species	Chloranthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11301	Ulmus glabra	Species	Ulmaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11097	Lepidium apetalum	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO2300	Actinidia deliciosa	Species	Actinidiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO463	Moschus berezovskii	Species	Moschidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11097	Lepidium apetalum	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11257	Momordica dioica	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO29221	Sarcandra glabra	Species	Chloranthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11301	Ulmus glabra	Species	Ulmaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11097	Lepidium apetalum	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO11257	Momordica dioica	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO463	Moschus berezovskii	Species	Moschidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO11097	Lepidium apetalum	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO29221	Sarcandra glabra	Species	Chloranthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO10399	Manfreda virginica	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16164	Podocarpus urbani	Species	Podocarpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17386	Securidaca longepedunculata	Species	Polygalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7048	Eucalyptus rariflora	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO936	Pinalia spicata	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19898	Stevia lucida	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9307	Ficus indica	Species	Ficidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2300	Actinidia deliciosa	Species	Actinidiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12998	Salvia rubescens	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5013	Loranthus spicatus	Species	Loranthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5392	Pachycereus pecten-aboriginum	Species	Cactaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12192	Coronilla scorpioides	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5827	Dalea tuberculata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6256	Eucalyptus umbra	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11301	Ulmus glabra	Species	Ulmaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10738	Cotoneaster horizontalis	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3740	Trisetum flavescens	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7345	Ptilonia magellanica	Species	Bonnemaisoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11555	Pterocaulon purpurascens	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3385	Cassine transvaalensis	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10577	Loranthus glaber	Species	Loranthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11257	Momordica dioica	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9512	Phlomis fruticosa	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8484	Codonopsis lanceolata	Species	Campanulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12891	Minasia alpestris	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11097	Lepidium apetalum	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9997	Pandanus dubius	Species	Pandanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29221	Sarcandra glabra	Species	Chloranthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6674	Burkholderia ambifaria	Species	Burkholderiaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO1185	Stereocaulon strictum	Species	Stereocaulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9928	Cephalaria cilicica	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9210	Desmodium uncinatum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO468	Dryopteris oligophlebia	Species	Dryopteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9040	Elsinoe annonae	Species	Elsinoaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11815	Mikania hirsutissima	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO463	Moschus berezovskii	Species	Moschidae	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	2

Activity Type	# Activity
NON-MOLECULAR	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	38.2	%	PMID[456003]
NPT27	Others	Unspecified		Activity	=	54.5	%	PMID[456003]

☑ 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 NPC106446 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	229
0.1-0.2	1459
0.2-0.3	4723
0.3-0.4	9662
0.4-0.5	12115
0.5-0.6	8038
0.6-0.7	5169
0.7-0.8	1232
0.8-0.85	66
0.85-0.9	3
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8704	High Similarity	NPC85670
0.8636	High Similarity	NPC257853
0.8609	High Similarity	NPC219656
0.8596	High Similarity	NPC203862
0.8509	High Similarity	NPC193382
0.8509	High Similarity	NPC99620
0.8509	High Similarity	NPC5311
0.8509	High Similarity	NPC199428
0.8509	High Similarity	NPC310341
0.8462	Intermediate Similarity	NPC233500
0.8435	Intermediate Similarity	NPC27507
0.8435	Intermediate Similarity	NPC243196
0.8435	Intermediate Similarity	NPC471354
0.8435	Intermediate Similarity	NPC244402
0.8435	Intermediate Similarity	NPC152615
0.8435	Intermediate Similarity	NPC84987
0.8435	Intermediate Similarity	NPC142066
0.8435	Intermediate Similarity	NPC309034
0.8435	Intermediate Similarity	NPC34390
0.8435	Intermediate Similarity	NPC196429
0.8435	Intermediate Similarity	NPC158344
0.8435	Intermediate Similarity	NPC290693
0.8435	Intermediate Similarity	NPC87250
0.8435	Intermediate Similarity	NPC471351
0.8435	Intermediate Similarity	NPC471355
0.8435	Intermediate Similarity	NPC93883
0.8435	Intermediate Similarity	NPC157376
0.8435	Intermediate Similarity	NPC99728
0.8435	Intermediate Similarity	NPC474418
0.8435	Intermediate Similarity	NPC50305
0.8435	Intermediate Similarity	NPC471353
0.8435	Intermediate Similarity	NPC473852
0.8435	Intermediate Similarity	NPC77319
0.8421	Intermediate Similarity	NPC84949
0.8421	Intermediate Similarity	NPC69576
0.8421	Intermediate Similarity	NPC471633
0.8421	Intermediate Similarity	NPC31354
0.839	Intermediate Similarity	NPC196130
0.8364	Intermediate Similarity	NPC82251
0.8362	Intermediate Similarity	NPC218093
0.8362	Intermediate Similarity	NPC83287
0.8333	Intermediate Similarity	NPC179261
0.8319	Intermediate Similarity	NPC219804
0.8291	Intermediate Similarity	NPC5883
0.8291	Intermediate Similarity	NPC291820
0.8291	Intermediate Similarity	NPC81222
0.8291	Intermediate Similarity	NPC292467
0.8291	Intermediate Similarity	NPC30483
0.8291	Intermediate Similarity	NPC470897
0.8291	Intermediate Similarity	NPC32177
0.8291	Intermediate Similarity	NPC153085
0.8291	Intermediate Similarity	NPC55532
0.8291	Intermediate Similarity	NPC44899
0.8291	Intermediate Similarity	NPC268326
0.8291	Intermediate Similarity	NPC304260
0.8291	Intermediate Similarity	NPC329905
0.8291	Intermediate Similarity	NPC469756
0.8291	Intermediate Similarity	NPC236973
0.8291	Intermediate Similarity	NPC29639
0.8235	Intermediate Similarity	NPC115349
0.822	Intermediate Similarity	NPC475136
0.822	Intermediate Similarity	NPC107607
0.822	Intermediate Similarity	NPC474466
0.822	Intermediate Similarity	NPC475629
0.822	Intermediate Similarity	NPC72260
0.822	Intermediate Similarity	NPC475556
0.8198	Intermediate Similarity	NPC239961
0.8174	Intermediate Similarity	NPC287075
0.8167	Intermediate Similarity	NPC27363
0.8165	Intermediate Similarity	NPC198992
0.8151	Intermediate Similarity	NPC475419
0.8151	Intermediate Similarity	NPC40749
0.8151	Intermediate Similarity	NPC120390
0.8151	Intermediate Similarity	NPC231518
0.8151	Intermediate Similarity	NPC475219
0.8151	Intermediate Similarity	NPC173555
0.8151	Intermediate Similarity	NPC475590
0.8151	Intermediate Similarity	NPC474908
0.8151	Intermediate Similarity	NPC314535
0.8145	Intermediate Similarity	NPC155529
0.8108	Intermediate Similarity	NPC200861
0.8108	Intermediate Similarity	NPC472822
0.8091	Intermediate Similarity	NPC121423
0.8083	Intermediate Similarity	NPC474423
0.8083	Intermediate Similarity	NPC27335
0.8083	Intermediate Similarity	NPC193893
0.8083	Intermediate Similarity	NPC471082
0.8083	Intermediate Similarity	NPC264336
0.8083	Intermediate Similarity	NPC74259
0.8073	Intermediate Similarity	NPC130792
0.8065	Intermediate Similarity	NPC254823
0.8049	Intermediate Similarity	NPC311534
0.8037	Intermediate Similarity	NPC329435
0.8033	Intermediate Similarity	NPC469750
0.8033	Intermediate Similarity	NPC250556
0.8017	Intermediate Similarity	NPC308262
0.8017	Intermediate Similarity	NPC117445
0.8017	Intermediate Similarity	NPC208193
0.8017	Intermediate Similarity	NPC84865
0.8	Intermediate Similarity	NPC133506
0.7984	Intermediate Similarity	NPC134902
0.7967	Intermediate Similarity	NPC117702
0.7967	Intermediate Similarity	NPC146456
0.7967	Intermediate Similarity	NPC179412
0.7967	Intermediate Similarity	NPC469757
0.7967	Intermediate Similarity	NPC329784
0.7967	Intermediate Similarity	NPC240070
0.7967	Intermediate Similarity	NPC471357
0.7967	Intermediate Similarity	NPC471356
0.7965	Intermediate Similarity	NPC475074
0.7953	Intermediate Similarity	NPC158350
0.7951	Intermediate Similarity	NPC226049
0.7946	Intermediate Similarity	NPC161775
0.7937	Intermediate Similarity	NPC24599
0.7917	Intermediate Similarity	NPC257610
0.7917	Intermediate Similarity	NPC470312
0.7899	Intermediate Similarity	NPC472080
0.7891	Intermediate Similarity	NPC127656
0.7881	Intermediate Similarity	NPC106228
0.7881	Intermediate Similarity	NPC212660
0.7881	Intermediate Similarity	NPC138372
0.7881	Intermediate Similarity	NPC207637
0.7874	Intermediate Similarity	NPC60150
0.7874	Intermediate Similarity	NPC192334
0.7869	Intermediate Similarity	NPC41129
0.7857	Intermediate Similarity	NPC472821
0.7857	Intermediate Similarity	NPC476824
0.784	Intermediate Similarity	NPC471358
0.784	Intermediate Similarity	NPC9499
0.784	Intermediate Similarity	NPC180079
0.784	Intermediate Similarity	NPC251866
0.784	Intermediate Similarity	NPC471352
0.784	Intermediate Similarity	NPC469753
0.784	Intermediate Similarity	NPC10823
0.784	Intermediate Similarity	NPC232785
0.784	Intermediate Similarity	NPC89514
0.784	Intermediate Similarity	NPC469752
0.784	Intermediate Similarity	NPC329986
0.784	Intermediate Similarity	NPC125077
0.784	Intermediate Similarity	NPC86159
0.784	Intermediate Similarity	NPC6108
0.784	Intermediate Similarity	NPC469755
0.784	Intermediate Similarity	NPC284406
0.784	Intermediate Similarity	NPC471361
0.784	Intermediate Similarity	NPC469754
0.784	Intermediate Similarity	NPC471360
0.784	Intermediate Similarity	NPC17896
0.784	Intermediate Similarity	NPC471359
0.784	Intermediate Similarity	NPC276838
0.784	Intermediate Similarity	NPC219085
0.784	Intermediate Similarity	NPC70542
0.784	Intermediate Similarity	NPC140092
0.784	Intermediate Similarity	NPC469751
0.784	Intermediate Similarity	NPC188234
0.784	Intermediate Similarity	NPC197707
0.7838	Intermediate Similarity	NPC280991
0.7838	Intermediate Similarity	NPC219038
0.7833	Intermediate Similarity	NPC477071
0.7833	Intermediate Similarity	NPC9674
0.7833	Intermediate Similarity	NPC19028
0.7826	Intermediate Similarity	NPC475030
0.7826	Intermediate Similarity	NPC316974
0.7826	Intermediate Similarity	NPC206618
0.7818	Intermediate Similarity	NPC79449
0.7818	Intermediate Similarity	NPC181147
0.7818	Intermediate Similarity	NPC474957
0.7807	Intermediate Similarity	NPC472820
0.7797	Intermediate Similarity	NPC178289
0.7795	Intermediate Similarity	NPC476097
0.7795	Intermediate Similarity	NPC470427
0.7795	Intermediate Similarity	NPC327664
0.7778	Intermediate Similarity	NPC470025
0.7778	Intermediate Similarity	NPC253456
0.7778	Intermediate Similarity	NPC159338
0.7778	Intermediate Similarity	NPC328074
0.7778	Intermediate Similarity	NPC321272
0.7778	Intermediate Similarity	NPC16569
0.7778	Intermediate Similarity	NPC317460
0.7778	Intermediate Similarity	NPC231797
0.7769	Intermediate Similarity	NPC170814
0.7768	Intermediate Similarity	NPC471599
0.7768	Intermediate Similarity	NPC200672
0.7768	Intermediate Similarity	NPC214714
0.7768	Intermediate Similarity	NPC472815
0.7768	Intermediate Similarity	NPC470972
0.7759	Intermediate Similarity	NPC316708
0.7759	Intermediate Similarity	NPC177047
0.7752	Intermediate Similarity	NPC289700
0.7752	Intermediate Similarity	NPC62172
0.775	Intermediate Similarity	NPC473617
0.775	Intermediate Similarity	NPC473828
0.775	Intermediate Similarity	NPC13710
0.7748	Intermediate Similarity	NPC244878
0.7739	Intermediate Similarity	NPC219900
0.7739	Intermediate Similarity	NPC38948
0.7739	Intermediate Similarity	NPC177524
0.7739	Intermediate Similarity	NPC217921
0.7739	Intermediate Similarity	NPC135015
0.7739	Intermediate Similarity	NPC311223
0.7739	Intermediate Similarity	NPC392

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 NPC106446 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	193
0.1-0.2	1628
0.2-0.3	3953
0.3-0.4	2296
0.4-0.5	637
0.5-0.6	300
0.6-0.7	127
0.7-0.8	16
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
0.8621	High Similarity	NPD7503	Approved
0.8362	Intermediate Similarity	NPD7328	Approved
0.8362	Intermediate Similarity	NPD7327	Approved
0.8291	Intermediate Similarity	NPD7516	Approved
0.822	Intermediate Similarity	NPD8377	Approved
0.822	Intermediate Similarity	NPD8294	Approved
0.8151	Intermediate Similarity	NPD8296	Approved
0.8151	Intermediate Similarity	NPD8378	Approved
0.8151	Intermediate Similarity	NPD8033	Approved
0.8151	Intermediate Similarity	NPD8380	Approved
0.8151	Intermediate Similarity	NPD8335	Approved
0.8151	Intermediate Similarity	NPD8379	Approved
0.8033	Intermediate Similarity	NPD7507	Approved
0.784	Intermediate Similarity	NPD7319	Approved
0.7739	Intermediate Similarity	NPD6686	Approved
0.735	Intermediate Similarity	NPD6412	Phase 2
0.7083	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7049	Intermediate Similarity	NPD6053	Discontinued
0.7043	Intermediate Similarity	NPD7638	Approved
0.7	Intermediate Similarity	NPD8293	Discontinued
0.6992	Remote Similarity	NPD8133	Approved
0.6983	Remote Similarity	NPD7640	Approved
0.6983	Remote Similarity	NPD7639	Approved
0.6953	Remote Similarity	NPD6370	Approved
0.6947	Remote Similarity	NPD7736	Approved
0.6897	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6885	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD7838	Discovery
0.6846	Remote Similarity	NPD7492	Approved
0.6825	Remote Similarity	NPD6009	Approved
0.6797	Remote Similarity	NPD6319	Approved
0.6797	Remote Similarity	NPD6054	Approved
0.6797	Remote Similarity	NPD6059	Approved
0.6794	Remote Similarity	NPD6616	Approved
0.6774	Remote Similarity	NPD6882	Approved
0.6752	Remote Similarity	NPD4225	Approved
0.6748	Remote Similarity	NPD6371	Approved
0.6744	Remote Similarity	NPD8513	Phase 3
0.6744	Remote Similarity	NPD8516	Approved
0.6744	Remote Similarity	NPD6015	Approved
0.6744	Remote Similarity	NPD8515	Approved
0.6744	Remote Similarity	NPD6016	Approved
0.6744	Remote Similarity	NPD8517	Approved
0.6742	Remote Similarity	NPD7078	Approved
0.6726	Remote Similarity	NPD46	Approved
0.6726	Remote Similarity	NPD6698	Approved
0.672	Remote Similarity	NPD4632	Approved
0.6713	Remote Similarity	NPD7625	Phase 1
0.6693	Remote Similarity	NPD7115	Discovery
0.6692	Remote Similarity	NPD5988	Approved
0.6667	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.664	Remote Similarity	NPD8297	Approved
0.6639	Remote Similarity	NPD5344	Discontinued
0.6639	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6636	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6585	Remote Similarity	NPD7320	Approved
0.6583	Remote Similarity	NPD7632	Discontinued
0.6557	Remote Similarity	NPD6008	Approved
0.6557	Remote Similarity	NPD5739	Approved
0.6557	Remote Similarity	NPD6402	Approved
0.6557	Remote Similarity	NPD6675	Approved
0.6557	Remote Similarity	NPD7128	Approved
0.6555	Remote Similarity	NPD6648	Approved
0.6532	Remote Similarity	NPD6373	Approved
0.6532	Remote Similarity	NPD6372	Approved
0.6515	Remote Similarity	NPD8328	Phase 3
0.6515	Remote Similarity	NPD6067	Discontinued
0.6515	Remote Similarity	NPD7604	Phase 2
0.6504	Remote Similarity	NPD5697	Approved
0.6504	Remote Similarity	NPD5701	Approved
0.6504	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.646	Remote Similarity	NPD7524	Approved
0.6452	Remote Similarity	NPD6881	Approved
0.6452	Remote Similarity	NPD6899	Approved
0.6429	Remote Similarity	NPD6650	Approved
0.6429	Remote Similarity	NPD6649	Approved
0.64	Remote Similarity	NPD6012	Approved
0.64	Remote Similarity	NPD6013	Approved
0.64	Remote Similarity	NPD6014	Approved
0.6387	Remote Similarity	NPD6083	Phase 2
0.6387	Remote Similarity	NPD6084	Phase 2
0.6379	Remote Similarity	NPD7637	Suspended
0.6372	Remote Similarity	NPD4249	Approved
0.6364	Remote Similarity	NPD5983	Phase 2
0.6356	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6356	Remote Similarity	NPD5695	Phase 3
0.6349	Remote Similarity	NPD7290	Approved
0.6349	Remote Similarity	NPD7102	Approved
0.6349	Remote Similarity	NPD6883	Approved
0.6348	Remote Similarity	NPD6051	Approved
0.6339	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6324	Remote Similarity	NPD6033	Approved
0.632	Remote Similarity	NPD6011	Approved
0.6316	Remote Similarity	NPD4250	Approved
0.6316	Remote Similarity	NPD4251	Approved
0.6308	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6304	Remote Similarity	NPD7260	Phase 2
0.6299	Remote Similarity	NPD6847	Approved
0.6299	Remote Similarity	NPD6869	Approved
0.6299	Remote Similarity	NPD6617	Approved
0.6299	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6299	Remote Similarity	NPD8130	Phase 1
0.6283	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6259	Remote Similarity	NPD6845	Suspended
0.625	Remote Similarity	NPD8074	Phase 3
0.625	Remote Similarity	NPD6695	Phase 3
0.625	Remote Similarity	NPD4755	Approved
0.6239	Remote Similarity	NPD5284	Approved
0.6239	Remote Similarity	NPD5281	Approved
0.623	Remote Similarity	NPD4159	Approved
0.622	Remote Similarity	NPD4634	Approved
0.6198	Remote Similarity	NPD5696	Approved
0.6186	Remote Similarity	NPD4202	Approved
0.6186	Remote Similarity	NPD8171	Discontinued
0.6179	Remote Similarity	NPD5211	Phase 2
0.6176	Remote Similarity	NPD6336	Discontinued
0.6172	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6148	Remote Similarity	NPD5286	Approved
0.6148	Remote Similarity	NPD4700	Approved
0.6148	Remote Similarity	NPD7829	Approved
0.6148	Remote Similarity	NPD4696	Approved
0.6148	Remote Similarity	NPD7830	Approved
0.6148	Remote Similarity	NPD5285	Approved
0.6134	Remote Similarity	NPD6001	Approved
0.6115	Remote Similarity	NPD5956	Approved
0.6107	Remote Similarity	NPD6274	Approved
0.6102	Remote Similarity	NPD5693	Phase 1
0.608	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.608	Remote Similarity	NPD5141	Approved
0.6068	Remote Similarity	NPD4753	Phase 2
0.6063	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.605	Remote Similarity	NPD5778	Approved
0.605	Remote Similarity	NPD5779	Approved
0.6048	Remote Similarity	NPD5226	Approved
0.6048	Remote Similarity	NPD5224	Approved
0.6048	Remote Similarity	NPD5225	Approved
0.6048	Remote Similarity	NPD4633	Approved
0.6034	Remote Similarity	NPD7750	Discontinued
0.6032	Remote Similarity	NPD4768	Approved
0.6032	Remote Similarity	NPD4767	Approved
0.6018	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6017	Remote Similarity	NPD5207	Approved
0.6017	Remote Similarity	NPD5692	Phase 3
0.6	Remote Similarity	NPD5282	Discontinued
0.6	Remote Similarity	NPD5175	Approved
0.6	Remote Similarity	NPD5174	Approved
0.5984	Remote Similarity	NPD5959	Approved
0.5983	Remote Similarity	NPD6903	Approved
0.5982	Remote Similarity	NPD6930	Phase 2
0.5982	Remote Similarity	NPD6931	Approved
0.5976	Remote Similarity	NPD7799	Discontinued
0.5971	Remote Similarity	NPD8336	Approved
0.5971	Remote Similarity	NPD8337	Approved
0.597	Remote Similarity	NPD7100	Approved
0.597	Remote Similarity	NPD7101	Approved
0.5968	Remote Similarity	NPD5223	Approved
0.5966	Remote Similarity	NPD6050	Approved
0.5966	Remote Similarity	NPD6411	Approved
0.5966	Remote Similarity	NPD7983	Approved
0.5966	Remote Similarity	NPD5694	Approved
0.5956	Remote Similarity	NPD8080	Discontinued
0.5948	Remote Similarity	NPD6684	Approved
0.5948	Remote Similarity	NPD7334	Approved
0.5948	Remote Similarity	NPD5330	Approved
0.5948	Remote Similarity	NPD5279	Phase 3
0.5948	Remote Similarity	NPD7521	Approved
0.5948	Remote Similarity	NPD7146	Approved
0.5948	Remote Similarity	NPD6409	Approved
0.5942	Remote Similarity	NPD8451	Approved
0.594	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.594	Remote Similarity	NPD6317	Approved
0.5938	Remote Similarity	NPD4730	Approved
0.5938	Remote Similarity	NPD4729	Approved
0.5932	Remote Similarity	NPD1695	Approved
0.5929	Remote Similarity	NPD6902	Approved
0.5917	Remote Similarity	NPD6399	Phase 3
0.5915	Remote Similarity	NPD8449	Approved
0.5913	Remote Similarity	NPD3666	Approved
0.5913	Remote Similarity	NPD3665	Phase 1
0.5913	Remote Similarity	NPD3133	Approved
0.5912	Remote Similarity	NPD7642	Approved
0.5909	Remote Similarity	NPD6933	Approved
0.5899	Remote Similarity	NPD8448	Approved
0.5897	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.5896	Remote Similarity	NPD6335	Approved
0.5896	Remote Similarity	NPD6313	Approved
0.5896	Remote Similarity	NPD6314	Approved
0.5893	Remote Similarity	NPD6929	Approved
0.5882	Remote Similarity	NPD6909	Approved
0.5882	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.5882	Remote Similarity	NPD6908	Approved
0.5882	Remote Similarity	NPD5785	Approved
0.5877	Remote Similarity	NPD5209	Approved
0.5874	Remote Similarity	NPD8450	Suspended
0.5873	Remote Similarity	NPD4754	Approved
0.5862	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.5862	Remote Similarity	NPD1694	Approved
0.5847	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.5846	Remote Similarity	NPD5248	Approved
0.5846	Remote Similarity	NPD5247	Approved

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