NPASS Compound

Structure

CID212874 OpenBabel06191716002D 31 36 0 0 1 0 0 0 0 0999 V2000 3.5823 -0.7833 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3104 -2.5218 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4132 -3.7047 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8947 -2.2520 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5691 0.9564 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1173 -1.7499 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2777 -1.2658 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0757 -1.6531 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1185 -4.6565 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6007 -3.2049 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2792 -4.1729 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7610 -2.7207 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0713 -1.6531 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9573 -3.2027 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7594 0.1856 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0757 0.0865 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5779 -0.7833 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 -1.5666 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.1179 -2.7191 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9576 -4.1714 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.4386 -1.7509 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.4392 -2.7201 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5990 -1.2667 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.9208 -0.2992 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.9208 -1.2674 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.2789 -3.2042 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7605 -1.7515 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.5691 -0.7833 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.0713 0.0865 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -6.8238 -4.6711 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 2 18 1 0 0 0 0 5 29 1 0 0 0 0 6 7 1 0 0 0 0 6 19 2 0 0 0 0 8 13 1 0 0 0 0 8 17 1 0 0 0 0 9 11 1 0 0 0 0 9 20 1 0 0 0 0 10 12 1 0 0 0 0 10 22 1 0 0 0 0 11 26 1 0 0 0 0 12 27 1 0 0 0 0 14 19 1 0 0 0 0 14 20 1 0 0 0 0 15 23 1 0 0 0 0 16 17 1 0 0 0 0 16 29 1 0 0 0 0 17 1 1 6 0 0 0 18 25 1 0 0 0 0 18 28 1 1 0 0 0 19 26 1 0 0 0 0 20 30 1 6 0 0 0 21 7 1 1 0 0 0 21 22 1 0 0 0 0 21 23 1 0 0 0 0 22 26 1 6 0 0 0 23 27 1 6 0 0 0 24 15 1 6 0 0 0 24 25 1 0 0 0 0 24 31 1 0 0 0 0 25 27 1 6 0 0 0 26 3 1 6 0 0 0 27 4 1 6 0 0 0 28 13 1 6 0 0 0 28 29 1 0 0 0 0 28 31 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	427.35
Volume:	467.446
LogP:	5.86
LogD:	4.606
LogS:	-5.608
# Rotatable Bonds:	0
TPSA:	32.7
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	6
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.509
Synthetic Accessibility Score:	5.434
Fsp3:	0.929
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.715
MDCK Permeability:	1.0502476470719557e-05
Pgp-inhibitor:	0.996
Pgp-substrate:	0.967
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.335
30% Bioavailability (F30%):	0.011

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.601
Plasma Protein Binding (PPB):	81.1874008178711%
Volume Distribution (VD):	3.446
Pgp-substrate:	10.390497207641602%

ADMET: Metabolism

CYP1A2-inhibitor:	0.052
CYP1A2-substrate:	0.571
CYP2C19-inhibitor:	0.161
CYP2C19-substrate:	0.958
CYP2C9-inhibitor:	0.266
CYP2C9-substrate:	0.054
CYP2D6-inhibitor:	0.288
CYP2D6-substrate:	0.693
CYP3A4-inhibitor:	0.745
CYP3A4-substrate:	0.865

ADMET: Excretion

Clearance (CL):	12.411
Half-life (T1/2):	0.085

ADMET: Toxicity

hERG Blockers:	0.982
Human Hepatotoxicity (H-HT):	0.406
Drug-inuced Liver Injury (DILI):	0.535
AMES Toxicity:	0.026
Rat Oral Acute Toxicity:	0.873
Maximum Recommended Daily Dose:	0.914
Skin Sensitization:	0.951
Carcinogencity:	0.736
Eye Corrosion:	0.231
Eye Irritation:	0.042
Respiratory Toxicity:	0.984

Download Data

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

Natural Product: NPC212874

Natural Product ID:	NPC212874
*Common Name:**	RPNUGHPOPSPHKR-XMSHHSNWSA-N
IUPAC Name:	n.a.
Synonyms:	N-Methylsolasodine
Standard InCHIKey:	RPNUGHPOPSPHKR-XMSHHSNWSA-N
Standard InCHI:	InChI=1S/C28H45NO2/c1-17-8-13-28(29(5)16-17)18(2)25-24(31-28)15-23-21-7-6-19-14-20(30)9-11-26(19,3)22(21)10-12-27(23,25)4/h6,17-18,20-25,30H,7-16H2,1-5H3/t17-,18+,20+,21-,22+,23+,24+,25+,26+,27+,28-/m1/s1
SMILES:	C[C@@H]1CC[C@@]2(N(C1)C)O[C@@H]1[C@H]([C@@H]2C)[C@@]2([C@@H](C1)[C@@H]1CC=C3[C@]([C@H]1CC2)(C)CC[C@@H](C3)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL519472
PubChem CID:	21573751
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0002724] Steroidal alkaloids [CHEMONTID:0001704] Spirosolanes and derivatives

*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
NPO14582	Spinacia oleracea	Species	Chenopodiaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/j.jfca.2005.08.001]
NPO15684	Cochliobolus heterostrophus	Species	Pleosporaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10395513]
NPO7093	Oncorhynchus keta	Species	Salmonidae	Eukaryota	eggs	Pacific	n.a.	PMID[10654418]
NPO7093	Oncorhynchus keta	Species	Salmonidae	Eukaryota	Eggs	n.a.	n.a.	PMID[10654418]
NPO15462	Angelica sinensis	Species	Apiaceae	Eukaryota	roots	purchased from Kiu Shun Trading Ltd., Vancouver, Canada	2000	PMID[16643021]
NPO14582	Spinacia oleracea	Species	Chenopodiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18460139]
NPO958	Tambja ceutae	Species	Polyceridae	Eukaryota	n.a.	Azorean	n.a.	PMID[20227875]
NPO15462	Angelica sinensis	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25538068]
NPO15462	Angelica sinensis	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27400088]
NPO14582	Spinacia oleracea	Species	Chenopodiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[6821187]
NPO14582	Spinacia oleracea	Species	Chenopodiaceae	Eukaryota	n.a.	leaf	n.a.	PMID[9433811]
NPO14582	Spinacia oleracea	Species	Chenopodiaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO14582	Spinacia oleracea	Species	Chenopodiaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO14582	Spinacia oleracea	Species	Chenopodiaceae	Eukaryota	Plant	n.a.	n.a.	Database[FooDB]
NPO7093	Oncorhynchus keta	Species	Salmonidae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO14582	Spinacia oleracea	Species	Chenopodiaceae	Eukaryota	Leaves	n.a.		Database[FooDB]
NPO6722	Anaphalis margaritacea	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO27244	Dysosma pleiantha	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO4847	Lasianthus wallichii	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO14582	Spinacia oleracea	Species	Chenopodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7377	Hemiphragma heterophyllum	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO6421	Neolitsea sericea	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15462	Angelica sinensis	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO14582	Spinacia oleracea	Species	Chenopodiaceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO6421	Neolitsea sericea	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6722	Anaphalis margaritacea	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14582	Spinacia oleracea	Species	Chenopodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4773	Pteromys volans	Species	Sciuridae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15462	Angelica sinensis	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7377	Hemiphragma heterophyllum	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO27244	Dysosma pleiantha	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4847	Lasianthus wallichii	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15462	Angelica sinensis	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO14582	Spinacia oleracea	Species	Chenopodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO6722	Anaphalis margaritacea	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO4773	Pteromys volans	Species	Sciuridae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO15462	Angelica sinensis	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO586	Lomandra hastilis	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5739	Rubus foliolosus	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27244	Dysosma pleiantha	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5518	Thuja dolabrata	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10450	Clerodendrum infortunatum	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15462	Angelica sinensis	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO241	Teucrium cossonii	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6722	Anaphalis margaritacea	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5809	Xanthoparmelia tinctina	Species	Parmeliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4847	Lasianthus wallichii	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1977	Arum montanum	Species	Araceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3528	Cinnamomum pedunculatum	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1244	Trimusculus conica	Species	Trimusculidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4050	Boronia lanceolata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO518	Mercurialis leiocarpa	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6951	Dictyota spinulosa	Species	Dictyotaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3023	Achillea pratensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14582	Spinacia oleracea	Species	Chenopodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15684	Cochliobolus heterostrophus	Species	Pleosporaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1659	Primula denticulata	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6421	Neolitsea sericea	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4125	Corydalis crystallina	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1814	Euphorbia cattimandoo	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4411	Plantago ovata	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4204	Ochradenus baccatus	Species	Resedaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3456	Eucalyptus campanulata	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO798	Chloranthus holostegius	Species	Chloranthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7161	Capparis angulata	Species	Capparaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7640	Klaseopsis chinensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7093	Oncorhynchus keta	Species	Salmonidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6345	Podocarpus sellowii	Species	Podocarpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9099	Carissa spinarum	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4773	Pteromys volans	Species	Sciuridae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16714	Campanula pendula	Species	Campanulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO958	Tambja ceutae	Species	Polyceridae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6523	Streptococcus pneumoniae	Species	Streptococcaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO3913	Alcea nudiflora	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4350	Chlorella pyrenoidosa	Species	Chlorellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2339	Turnera ulmifolia	Species	Passifloraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7377	Hemiphragma heterophyllum	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6107	Acacia lemmoni	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

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

NP Quantity Composition/Concentration

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

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

Biological Activity

Activity Type	# Activity
ED50	2

Activity Type	# Activity
Cell Line	1
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	ED50	=	6.0	ug ml-1	PMID[543276]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	ED50	=	8.02	ug ml-1	PMID[543276]

☑ 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 NPC212874 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	104
0.1-0.2	951
0.2-0.3	9790
0.3-0.4	15707
0.4-0.5	8297
0.5-0.6	6335
0.6-0.7	1399
0.7-0.8	102
0.8-0.85	4
0.85-0.9	3
0.9-0.95	4
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9216	High Similarity	NPC85001
0.9216	High Similarity	NPC253645
0.9216	High Similarity	NPC95920
0.9216	High Similarity	NPC147835
0.8835	High Similarity	NPC46981
0.87	High Similarity	NPC91604
0.8627	High Similarity	NPC176012
0.8235	Intermediate Similarity	NPC474164
0.8137	Intermediate Similarity	NPC289140
0.8041	Intermediate Similarity	NPC75810
0.7885	Intermediate Similarity	NPC140300
0.7876	Intermediate Similarity	NPC304646
0.7876	Intermediate Similarity	NPC28280
0.7857	Intermediate Similarity	NPC478137
0.7748	Intermediate Similarity	NPC287764
0.7706	Intermediate Similarity	NPC86906
0.7705	Intermediate Similarity	NPC25455
0.7705	Intermediate Similarity	NPC15249
0.7692	Intermediate Similarity	NPC155985
0.7642	Intermediate Similarity	NPC122819
0.7619	Intermediate Similarity	NPC476903
0.7615	Intermediate Similarity	NPC475239
0.7596	Intermediate Similarity	NPC243985
0.7596	Intermediate Similarity	NPC280710
0.7593	Intermediate Similarity	NPC50815
0.7581	Intermediate Similarity	NPC147753
0.7581	Intermediate Similarity	NPC150057
0.7547	Intermediate Similarity	NPC240650
0.7524	Intermediate Similarity	NPC272732
0.7524	Intermediate Similarity	NPC311164
0.7523	Intermediate Similarity	NPC241879
0.75	Intermediate Similarity	NPC477522
0.75	Intermediate Similarity	NPC476503
0.75	Intermediate Similarity	NPC242419
0.75	Intermediate Similarity	NPC296686
0.75	Intermediate Similarity	NPC93027
0.75	Intermediate Similarity	NPC235126
0.7479	Intermediate Similarity	NPC478138
0.7456	Intermediate Similarity	NPC476498
0.7438	Intermediate Similarity	NPC94881
0.7438	Intermediate Similarity	NPC265275
0.7438	Intermediate Similarity	NPC48886
0.7431	Intermediate Similarity	NPC247060
0.7407	Intermediate Similarity	NPC135799
0.7395	Intermediate Similarity	NPC476504
0.7374	Intermediate Similarity	NPC5985
0.7368	Intermediate Similarity	NPC79238
0.7347	Intermediate Similarity	NPC26117
0.7344	Intermediate Similarity	NPC287885
0.7328	Intermediate Similarity	NPC476499
0.7327	Intermediate Similarity	NPC474349
0.7327	Intermediate Similarity	NPC474189
0.7308	Intermediate Similarity	NPC84171
0.7292	Intermediate Similarity	NPC107059
0.7292	Intermediate Similarity	NPC321381
0.7292	Intermediate Similarity	NPC96319
0.7292	Intermediate Similarity	NPC321016
0.7273	Intermediate Similarity	NPC471083
0.7245	Intermediate Similarity	NPC1319
0.7236	Intermediate Similarity	NPC317654
0.7236	Intermediate Similarity	NPC96010
0.7228	Intermediate Similarity	NPC209802
0.7222	Intermediate Similarity	NPC177818
0.7216	Intermediate Similarity	NPC198968
0.7216	Intermediate Similarity	NPC318495
0.7216	Intermediate Similarity	NPC155986
0.7207	Intermediate Similarity	NPC293299
0.7207	Intermediate Similarity	NPC45365
0.72	Intermediate Similarity	NPC1272
0.72	Intermediate Similarity	NPC470614
0.7188	Intermediate Similarity	NPC136188
0.7188	Intermediate Similarity	NPC230301
0.7188	Intermediate Similarity	NPC22105
0.7188	Intermediate Similarity	NPC28657
0.7188	Intermediate Similarity	NPC304309
0.7188	Intermediate Similarity	NPC134847
0.7188	Intermediate Similarity	NPC288035
0.7188	Intermediate Similarity	NPC162742
0.7188	Intermediate Similarity	NPC285893
0.7182	Intermediate Similarity	NPC118275
0.7143	Intermediate Similarity	NPC474216
0.7143	Intermediate Similarity	NPC473943
0.7143	Intermediate Similarity	NPC477514
0.7143	Intermediate Similarity	NPC87604
0.7113	Intermediate Similarity	NPC240604
0.7113	Intermediate Similarity	NPC300324
0.7113	Intermediate Similarity	NPC113733
0.7105	Intermediate Similarity	NPC159367
0.71	Intermediate Similarity	NPC474731
0.71	Intermediate Similarity	NPC474759
0.71	Intermediate Similarity	NPC474752
0.71	Intermediate Similarity	NPC7505
0.71	Intermediate Similarity	NPC474683
0.71	Intermediate Similarity	NPC82986
0.7087	Intermediate Similarity	NPC24277
0.7071	Intermediate Similarity	NPC28862
0.7071	Intermediate Similarity	NPC81306
0.7071	Intermediate Similarity	NPC47982
0.7071	Intermediate Similarity	NPC109546
0.7071	Intermediate Similarity	NPC84694
0.7071	Intermediate Similarity	NPC143182
0.7071	Intermediate Similarity	NPC328714
0.7059	Intermediate Similarity	NPC124172
0.7041	Intermediate Similarity	NPC34019
0.703	Intermediate Similarity	NPC201852
0.703	Intermediate Similarity	NPC20853
0.7027	Intermediate Similarity	NPC176406
0.7027	Intermediate Similarity	NPC474022
0.7018	Intermediate Similarity	NPC25340
0.701	Intermediate Similarity	NPC141071
0.701	Intermediate Similarity	NPC257347
0.701	Intermediate Similarity	NPC471723
0.7009	Intermediate Similarity	NPC98193
0.7	Intermediate Similarity	NPC164840
0.7	Intermediate Similarity	NPC234193
0.7	Intermediate Similarity	NPC241290
0.7	Intermediate Similarity	NPC209944
0.6991	Remote Similarity	NPC119329
0.697	Remote Similarity	NPC307965
0.697	Remote Similarity	NPC76931
0.697	Remote Similarity	NPC275910
0.697	Remote Similarity	NPC18603
0.6961	Remote Similarity	NPC475789
0.6952	Remote Similarity	NPC471952
0.6952	Remote Similarity	NPC470542
0.6939	Remote Similarity	NPC129165
0.6939	Remote Similarity	NPC134330
0.6939	Remote Similarity	NPC189883
0.6931	Remote Similarity	NPC474531
0.6931	Remote Similarity	NPC23852
0.6931	Remote Similarity	NPC470383
0.6931	Remote Similarity	NPC264245
0.6931	Remote Similarity	NPC47761
0.6931	Remote Similarity	NPC209620
0.693	Remote Similarity	NPC195841
0.693	Remote Similarity	NPC233256
0.6923	Remote Similarity	NPC474970
0.6923	Remote Similarity	NPC293287
0.6923	Remote Similarity	NPC152808
0.6903	Remote Similarity	NPC475701
0.6903	Remote Similarity	NPC474583
0.6903	Remote Similarity	NPC98765
0.69	Remote Similarity	NPC30986
0.69	Remote Similarity	NPC209430
0.6893	Remote Similarity	NPC474047
0.6887	Remote Similarity	NPC105495
0.687	Remote Similarity	NPC169375
0.6869	Remote Similarity	NPC214570
0.6864	Remote Similarity	NPC56796
0.6863	Remote Similarity	NPC248886
0.6863	Remote Similarity	NPC49964
0.6863	Remote Similarity	NPC189972
0.6863	Remote Similarity	NPC50964
0.6863	Remote Similarity	NPC101462
0.6863	Remote Similarity	NPC470049
0.6857	Remote Similarity	NPC271967
0.6847	Remote Similarity	NPC309493
0.6842	Remote Similarity	NPC474464
0.6838	Remote Similarity	NPC472313
0.6838	Remote Similarity	NPC63511
0.6832	Remote Similarity	NPC236112
0.6829	Remote Similarity	NPC238323
0.6827	Remote Similarity	NPC266511
0.6827	Remote Similarity	NPC318390
0.6827	Remote Similarity	NPC274448
0.6827	Remote Similarity	NPC157257
0.6818	Remote Similarity	NPC304899
0.6818	Remote Similarity	NPC253115
0.6814	Remote Similarity	NPC476755
0.6804	Remote Similarity	NPC474140
0.6804	Remote Similarity	NPC471799
0.6803	Remote Similarity	NPC35037
0.68	Remote Similarity	NPC285761
0.68	Remote Similarity	NPC244385
0.68	Remote Similarity	NPC138621
0.68	Remote Similarity	NPC6978
0.68	Remote Similarity	NPC167037
0.6796	Remote Similarity	NPC110778
0.6796	Remote Similarity	NPC317458
0.6796	Remote Similarity	NPC477818
0.6796	Remote Similarity	NPC474634
0.6794	Remote Similarity	NPC297058
0.6792	Remote Similarity	NPC2158
0.6792	Remote Similarity	NPC328313
0.6786	Remote Similarity	NPC275686
0.6786	Remote Similarity	NPC83709
0.6783	Remote Similarity	NPC55462
0.6783	Remote Similarity	NPC477292
0.6783	Remote Similarity	NPC474015
0.6783	Remote Similarity	NPC181845
0.678	Remote Similarity	NPC474459
0.6774	Remote Similarity	NPC469943
0.6768	Remote Similarity	NPC244488
0.6768	Remote Similarity	NPC73875
0.6768	Remote Similarity	NPC46160
0.6768	Remote Similarity	NPC470362
0.6768	Remote Similarity	NPC202642
0.6768	Remote Similarity	NPC247325
0.6768	Remote Similarity	NPC237460
0.6765	Remote Similarity	NPC70927

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 NPC212874 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	103
0.1-0.2	606
0.2-0.3	3393
0.3-0.4	3711
0.4-0.5	908
0.5-0.6	331
0.6-0.7	91
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
0.7642	Intermediate Similarity	NPD8449	Approved
0.7581	Intermediate Similarity	NPD8450	Suspended
0.7292	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD6942	Approved
0.7188	Intermediate Similarity	NPD7339	Approved
0.7119	Intermediate Similarity	NPD7755	Approved
0.7119	Intermediate Similarity	NPD7754	Approved
0.6818	Remote Similarity	NPD5349	Clinical (unspecified phase)
0.6783	Remote Similarity	NPD7333	Discontinued
0.6735	Remote Similarity	NPD4784	Approved
0.6735	Remote Similarity	NPD4785	Approved
0.6731	Remote Similarity	NPD4786	Approved
0.6723	Remote Similarity	NPD7335	Phase 2
0.6723	Remote Similarity	NPD7337	Clinical (unspecified phase)
0.6723	Remote Similarity	NPD7336	Phase 2
0.6701	Remote Similarity	NPD4243	Approved
0.6698	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7525	Registered
0.6581	Remote Similarity	NPD7646	Clinical (unspecified phase)
0.6577	Remote Similarity	NPD7991	Discontinued
0.6569	Remote Similarity	NPD7645	Phase 2
0.6566	Remote Similarity	NPD6926	Approved
0.6566	Remote Similarity	NPD6924	Approved
0.656	Remote Similarity	NPD6909	Approved
0.656	Remote Similarity	NPD6908	Approved
0.6538	Remote Similarity	NPD3667	Approved
0.6505	Remote Similarity	NPD4748	Discontinued
0.6446	Remote Similarity	NPD8078	Approved
0.6446	Remote Similarity	NPD8077	Approved
0.6436	Remote Similarity	NPD6933	Approved
0.6415	Remote Similarity	NPD3665	Phase 1
0.6415	Remote Similarity	NPD3666	Approved
0.6415	Remote Similarity	NPD3133	Approved
0.6396	Remote Similarity	NPD6399	Phase 3
0.6364	Remote Similarity	NPD7150	Approved
0.6364	Remote Similarity	NPD7151	Approved
0.6364	Remote Similarity	NPD7152	Approved
0.6337	Remote Similarity	NPD5275	Approved
0.6337	Remote Similarity	NPD4190	Phase 3
0.633	Remote Similarity	NPD4722	Approved
0.633	Remote Similarity	NPD4723	Approved
0.6327	Remote Similarity	NPD6923	Approved
0.6327	Remote Similarity	NPD6922	Approved
0.6321	Remote Similarity	NPD6695	Phase 3
0.6273	Remote Similarity	NPD5328	Approved
0.627	Remote Similarity	NPD7518	Approved
0.627	Remote Similarity	NPD7517	Approved
0.627	Remote Similarity	NPD7519	Approved
0.6263	Remote Similarity	NPD7144	Approved
0.6263	Remote Similarity	NPD7143	Approved
0.6262	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.625	Remote Similarity	NPD4202	Approved
0.625	Remote Similarity	NPD6929	Approved
0.625	Remote Similarity	NPD4195	Approved
0.6218	Remote Similarity	NPD6920	Discontinued
0.6202	Remote Similarity	NPD7122	Discontinued
0.619	Remote Similarity	NPD6930	Phase 2
0.619	Remote Similarity	NPD6931	Approved
0.6186	Remote Similarity	NPD7911	Approved
0.6186	Remote Similarity	NPD7986	Approved
0.6186	Remote Similarity	NPD7987	Approved
0.6186	Remote Similarity	NPD7912	Approved
0.6182	Remote Similarity	NPD6903	Approved
0.6182	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6174	Remote Similarity	NPD6084	Phase 2
0.6174	Remote Similarity	NPD6083	Phase 2
0.6161	Remote Similarity	NPD6079	Approved
0.6154	Remote Similarity	NPD4159	Approved
0.6147	Remote Similarity	NPD5330	Approved
0.6147	Remote Similarity	NPD3618	Phase 1
0.6147	Remote Similarity	NPD7146	Approved
0.6147	Remote Similarity	NPD7521	Approved
0.6147	Remote Similarity	NPD7334	Approved
0.6147	Remote Similarity	NPD6409	Approved
0.6147	Remote Similarity	NPD6684	Approved
0.6126	Remote Similarity	NPD6051	Approved
0.6126	Remote Similarity	NPD4753	Phase 2
0.6116	Remote Similarity	NPD6415	Discontinued
0.6116	Remote Similarity	NPD7320	Approved
0.6091	Remote Similarity	NPD7524	Approved
0.6091	Remote Similarity	NPD7750	Discontinued
0.6083	Remote Similarity	NPD6402	Approved
0.6083	Remote Similarity	NPD7128	Approved
0.6083	Remote Similarity	NPD8040	Discontinued
0.6083	Remote Similarity	NPD5739	Approved
0.6083	Remote Similarity	NPD6675	Approved
0.6075	Remote Similarity	NPD4221	Approved
0.6075	Remote Similarity	NPD4223	Phase 3
0.6058	Remote Similarity	NPD6925	Approved
0.6058	Remote Similarity	NPD5776	Phase 2
0.6058	Remote Similarity	NPD6932	Approved
0.6055	Remote Similarity	NPD5329	Approved
0.6053	Remote Similarity	NPD5771	Approved
0.6053	Remote Similarity	NPD5707	Approved
0.6038	Remote Similarity	NPD7509	Discontinued
0.6038	Remote Similarity	NPD6928	Phase 2
0.6034	Remote Similarity	NPD4755	Approved
0.6034	Remote Similarity	NPD7920	Phase 3
0.6034	Remote Similarity	NPD7919	Phase 3
0.6033	Remote Similarity	NPD6412	Phase 2
0.6033	Remote Similarity	NPD7990	Approved
0.6033	Remote Similarity	NPD7989	Approved
0.6	Remote Similarity	NPD7725	Approved
0.6	Remote Similarity	NPD7145	Approved
0.5984	Remote Similarity	NPD6881	Approved
0.5984	Remote Similarity	NPD6899	Approved
0.5983	Remote Similarity	NPD8088	Phase 1
0.5983	Remote Similarity	NPD7638	Approved
0.5963	Remote Similarity	NPD4197	Approved
0.5963	Remote Similarity	NPD3668	Phase 3
0.5943	Remote Similarity	NPD6683	Phase 2
0.5935	Remote Similarity	NPD6372	Approved
0.5935	Remote Similarity	NPD6373	Approved
0.5932	Remote Similarity	NPD7639	Approved
0.5932	Remote Similarity	NPD7640	Approved
0.5932	Remote Similarity	NPD4700	Approved
0.5932	Remote Similarity	NPD5285	Approved
0.5932	Remote Similarity	NPD5286	Approved
0.5932	Remote Similarity	NPD4696	Approved
0.5909	Remote Similarity	NPD6893	Approved
0.5909	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.5902	Remote Similarity	NPD5697	Approved
0.5902	Remote Similarity	NPD5701	Approved
0.5891	Remote Similarity	NPD7522	Discontinued
0.5888	Remote Similarity	NPD7514	Phase 3
0.5887	Remote Similarity	NPD7102	Approved
0.5887	Remote Similarity	NPD7290	Approved
0.5887	Remote Similarity	NPD6420	Discontinued
0.5887	Remote Similarity	NPD6883	Approved
0.5882	Remote Similarity	NPD5223	Approved
0.5877	Remote Similarity	NPD7087	Discontinued
0.5872	Remote Similarity	NPD4788	Approved
0.5862	Remote Similarity	NPD4629	Approved
0.5862	Remote Similarity	NPD5695	Phase 3
0.5862	Remote Similarity	NPD5210	Approved
0.5862	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.5857	Remote Similarity	NPD6333	Approved
0.5857	Remote Similarity	NPD6334	Approved
0.5856	Remote Similarity	NPD8308	Discontinued
0.5856	Remote Similarity	NPD4688	Approved
0.5856	Remote Similarity	NPD6098	Approved
0.5856	Remote Similarity	NPD5279	Phase 3
0.5856	Remote Similarity	NPD4689	Approved
0.5856	Remote Similarity	NPD5205	Approved
0.5856	Remote Similarity	NPD4693	Phase 3
0.5856	Remote Similarity	NPD4138	Approved
0.5856	Remote Similarity	NPD4690	Approved
0.5854	Remote Similarity	NPD6011	Approved
0.5849	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.5847	Remote Similarity	NPD5696	Approved
0.584	Remote Similarity	NPD6847	Approved
0.584	Remote Similarity	NPD8130	Phase 1
0.584	Remote Similarity	NPD6650	Approved
0.584	Remote Similarity	NPD6617	Approved
0.584	Remote Similarity	NPD6649	Approved
0.584	Remote Similarity	NPD6869	Approved
0.584	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.5833	Remote Similarity	NPD6902	Approved
0.5833	Remote Similarity	NPD5226	Approved
0.5833	Remote Similarity	NPD5211	Phase 2
0.5833	Remote Similarity	NPD5225	Approved
0.5833	Remote Similarity	NPD4633	Approved
0.5833	Remote Similarity	NPD5224	Approved
0.582	Remote Similarity	NPD6640	Phase 3
0.582	Remote Similarity	NPD6008	Approved
0.5814	Remote Similarity	NPD7328	Approved
0.5814	Remote Similarity	NPD7327	Approved
0.5812	Remote Similarity	NPD4697	Phase 3
0.5812	Remote Similarity	NPD5221	Approved
0.5812	Remote Similarity	NPD5222	Approved
0.5812	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.5806	Remote Similarity	NPD6013	Approved
0.5806	Remote Similarity	NPD6012	Approved
0.5806	Remote Similarity	NPD6014	Approved
0.5802	Remote Similarity	NPD8033	Approved
0.5794	Remote Similarity	NPD8297	Approved
0.5794	Remote Similarity	NPD6882	Approved
0.5789	Remote Similarity	NPD4096	Approved
0.5789	Remote Similarity	NPD4001	Clinical (unspecified phase)
0.5785	Remote Similarity	NPD4754	Approved
0.5785	Remote Similarity	NPD5174	Approved
0.5785	Remote Similarity	NPD5175	Approved
0.5776	Remote Similarity	NPD7748	Approved
0.5769	Remote Similarity	NPD7516	Approved
0.5763	Remote Similarity	NPD5173	Approved
0.5752	Remote Similarity	NPD5737	Approved
0.5752	Remote Similarity	NPD6672	Approved
0.5741	Remote Similarity	NPD7332	Phase 2
0.5739	Remote Similarity	NPD8034	Phase 2
0.5739	Remote Similarity	NPD8035	Phase 2
0.5739	Remote Similarity	NPD7515	Phase 2
0.5738	Remote Similarity	NPD5141	Approved
0.5725	Remote Similarity	NPD8377	Approved
0.5725	Remote Similarity	NPD6054	Approved
0.5725	Remote Similarity	NPD8294	Approved
0.5725	Remote Similarity	NPD6845	Suspended
0.5725	Remote Similarity	NPD6059	Approved
0.5714	Remote Similarity	NPD5280	Approved
0.5714	Remote Similarity	NPD5690	Phase 2
0.5714	Remote Similarity	NPD8264	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