NPASS Compound

Structure

CID122828 OpenBabel06191715482D 21 23 0 0 1 0 0 0 0 0999 V2000 -3.4641 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 1 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 -1.7321 -3.0000 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 -3.4641 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 20 1 0 0 0 0 2 3 2 0 0 0 0 2 4 1 0 0 0 0 3 5 1 0 0 0 0 4 6 2 0 0 0 0 5 9 2 0 0 0 0 6 9 1 0 0 0 0 7 10 2 0 0 0 0 7 11 1 0 0 0 0 8 10 1 0 0 0 0 8 12 2 0 0 0 0 10 20 1 0 0 0 0 11 13 2 0 0 0 0 11 17 1 0 0 0 0 12 13 1 0 0 0 0 12 21 1 0 0 0 0 13 14 1 0 0 0 0 14 15 1 0 0 0 0 14 18 2 0 0 0 0 15 16 1 0 0 0 0 15 19 1 1 0 0 0 16 9 1 6 0 0 0 16 21 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	286.08
Volume:	285.119
LogP:	2.097
LogD:	0.933
LogS:	-2.784
# Rotatable Bonds:	2
TPSA:	75.99
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.884
Synthetic Accessibility Score:	3.171
Fsp3:	0.188
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.968
MDCK Permeability:	7.742542038613465e-06
Pgp-inhibitor:	0.002
Pgp-substrate:	0.075
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.005
30% Bioavailability (F30%):	0.004

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.255
Plasma Protein Binding (PPB):	91.31402587890625%
Volume Distribution (VD):	0.951
Pgp-substrate:	5.78197717666626%

ADMET: Metabolism

CYP1A2-inhibitor:	0.132
CYP1A2-substrate:	0.356
CYP2C19-inhibitor:	0.173
CYP2C19-substrate:	0.86
CYP2C9-inhibitor:	0.533
CYP2C9-substrate:	0.941
CYP2D6-inhibitor:	0.209
CYP2D6-substrate:	0.701
CYP3A4-inhibitor:	0.124
CYP3A4-substrate:	0.607

ADMET: Excretion

Clearance (CL):	4.372
Half-life (T1/2):	0.391

ADMET: Toxicity

hERG Blockers:	0.072
Human Hepatotoxicity (H-HT):	0.404
Drug-inuced Liver Injury (DILI):	0.954
AMES Toxicity:	0.073
Rat Oral Acute Toxicity:	0.175
Maximum Recommended Daily Dose:	0.755
Skin Sensitization:	0.477
Carcinogencity:	0.03
Eye Corrosion:	0.003
Eye Irritation:	0.466
Respiratory Toxicity:	0.367

Download Data

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

Natural Product: NPC122828

Natural Product ID:	NPC122828
*Common Name:**	(2R,3R)-Alpinone
IUPAC Name:	(2R,3R)-3,5-dihydroxy-7-methoxy-2-phenyl-2,3-dihydrochromen-4-one
Synonyms:	(2R,3R)-Alpinone
Standard InCHIKey:	QPOCKDYYXFOBCM-JKSUJKDBSA-N
Standard InCHI:	InChI=1S/C16H14O5/c1-20-10-7-11(17)13-12(8-10)21-16(15(19)14(13)18)9-5-3-2-4-6-9/h2-8,15-17,19H,1H3/t15-,16+/m0/s1
SMILES:	COc1cc(c2c(c1)O[C@H](c1ccccc1)[C@H](C2=O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1081328
PubChem CID:	46883390
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0002585] O-methylated flavonoids [CHEMONTID:0002592] 7-O-methylated flavonoids

*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
NPO17520	Erythrina subumbrans	Species	Fabaceae	Eukaryota	n.a.	stem	n.a.	PMID[17055201]
NPO17520	Erythrina subumbrans	Species	Fabaceae	Eukaryota	n.a.	bark	n.a.	PMID[17055201]
NPO12006	Apis mellifera	Species	Apidae	Eukaryota	n.a.	n.a.	n.a.	PMID[17548953]
NPO17520	Erythrina subumbrans	Species	Fabaceae	Eukaryota	Barks	n.a.	n.a.	PMID[18171023]
NPO13784	Dalbergia candenatensis	Species	Fabaceae	Eukaryota	heartwood	n.a.	n.a.	PMID[19653666]
NPO13379	Schizanthus tricolor	Species	Solanaceae	Eukaryota	Aerial parts	n.a.	n.a.	PMID[20166702]
NPO40884	Mexican propolis	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[20307087]
NPO11266	Garcinia cambogia	Species	Clusiaceae	Eukaryota	n.a.	exocarp	n.a.	PMID[21114277]
NPO13379	Schizanthus tricolor	Species	Solanaceae	Eukaryota	n.a.	aerial part	n.a.	PMID[21171571]
NPO14559	Acer saccharum	Species	Sapindaceae	Eukaryota	bark	n.a.	n.a.	PMID[22032697]
NPO14559	Acer saccharum	Species	Sapindaceae	Eukaryota	n.a.	bark	n.a.	PMID[22032697]
NPO12006	Apis mellifera	Species	Apidae	Eukaryota	n.a.	n.a.	n.a.	PMID[24675423]
NPO12006	Apis mellifera	Species	Apidae	Eukaryota	n.a.	Gedo, Ethiopia		PMID[24926420]
NPO12006	Apis mellifera	Species	Apidae	Eukaryota	n.a.	Holleta, Ethiopia		PMID[24926420]
NPO12006	Apis mellifera	Species	Apidae	Eukaryota	n.a.	Bako, Ethiopia		PMID[24926420]
NPO12006	Apis mellifera	Species	Apidae	Eukaryota	n.a.	Enemore, Ethiopia		PMID[24926420]
NPO14561	Walsura yunnanensis	Species	Meliaceae	Eukaryota	Leaves; Twigs	n.a.	n.a.	PMID[25075875]
NPO3013	Clathria basilana	Species	Microcionidae	Eukaryota	n.a.	n.a.	n.a.	PMID[29094598]
NPO13784	Dalbergia candenatensis	Species	Fabaceae	Eukaryota	n.a.	Thai	n.a.	PMID[3430167]
NPO2924	Pinus excelsa	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO13473	Anodendron affine	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO12006	Apis mellifera	Species	Apidae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11842	Petasites laevigatus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO14559	Acer saccharum	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7541	Ormosia hosiei	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO17299	Stephania discolor	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11266	Garcinia cambogia	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11842	Petasites laevigatus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14559	Acer saccharum	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14561	Walsura yunnanensis	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7541	Ormosia hosiei	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17299	Stephania discolor	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11266	Garcinia cambogia	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13473	Anodendron affine	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2924	Pinus excelsa	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7541	Ormosia hosiei	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO12006	Apis mellifera	Species	Apidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO7541	Ormosia hosiei	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11371	Psychotria leiocarpa	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9946	Roemeria hybrida	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5022	Viguiera arenaria	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11842	Petasites laevigatus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17918	Pinus clausa	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9131	Cryptostylis fulva	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14470	Polypodium decumanum	Species	Polypodiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13669	Hertia cheirifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14169	Acrocarpia paniculata	Species	Sargassaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17069	Argemone aenea	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13178	Ornithoglossum viride	Species	Colchicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2924	Pinus excelsa	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13876	Cedrela salvadorensis	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13473	Anodendron affine	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9569	Licaria chrysophylla	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11266	Garcinia cambogia	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14559	Acer saccharum	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14960	Angelica pancicii	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5280	Rubia tetragona	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13784	Dalbergia candenatensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12006	Apis mellifera	Species	Apidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21693	Pinus morrisonicola	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14369	Pocillopora eydouxi	Species	Pocilloporidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13379	Schizanthus tricolor	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17299	Stephania discolor	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14561	Walsura yunnanensis	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4700	Pertusaria truncata	Species	Pertusariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16998	Nannizzia gypsea	Species	Arthrodermataceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13537	Piper rugosum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12521	Sphaeranthus confertifolius	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17520	Erythrina subumbrans	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14804	Celastrus kusanoi	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3013	Clathria basilana	Species	Microcionidae	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
IC50	4
Others	1

Activity Type	# Activity
Cell Line	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT139	Cell Line	HT-29	Homo sapiens	IC50	=	46500.0	nM	PMID[479331]
NPT91	Cell Line	KB	Homo sapiens	IC50	=	73800.0	nM	PMID[479331]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	49300.0	nM	PMID[479331]
NPT165	Cell Line	HeLa	Homo sapiens	IC50	=	79000.0	nM	PMID[479331]
NPT461	Cell Line	PANC-1	Homo sapiens	PC50	=	74.2	uM	PMID[479332]

☑ 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 NPC122828 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	367
0.1-0.2	1458
0.2-0.3	3950
0.3-0.4	9553
0.4-0.5	8702
0.5-0.6	3686
0.6-0.7	5345
0.7-0.8	5190
0.8-0.85	2590
0.85-0.9	1388
0.9-0.95	416
0.95-1	52

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC176869
1.0	High Similarity	NPC3779
1.0	High Similarity	NPC44721
1.0	High Similarity	NPC40086
1.0	High Similarity	NPC476182
1.0	High Similarity	NPC211466
0.9857	High Similarity	NPC208176
0.9857	High Similarity	NPC142731
0.9857	High Similarity	NPC306607
0.9857	High Similarity	NPC49130
0.9857	High Similarity	NPC326506
0.9857	High Similarity	NPC4152
0.9857	High Similarity	NPC279417
0.9857	High Similarity	NPC62290
0.9787	High Similarity	NPC1940
0.9787	High Similarity	NPC148011
0.9722	High Similarity	NPC254412
0.9722	High Similarity	NPC262038
0.9722	High Similarity	NPC278476
0.9722	High Similarity	NPC262039
0.9722	High Similarity	NPC319910
0.9718	High Similarity	NPC472918
0.9655	High Similarity	NPC243171
0.9655	High Similarity	NPC138288
0.9655	High Similarity	NPC171651
0.9655	High Similarity	NPC35567
0.9655	High Similarity	NPC217149
0.9655	High Similarity	NPC216035
0.9653	High Similarity	NPC105136
0.965	High Similarity	NPC218569
0.9648	High Similarity	NPC229190
0.9589	High Similarity	NPC293286
0.9583	High Similarity	NPC277032
0.9583	High Similarity	NPC477941
0.958	High Similarity	NPC21835
0.9524	High Similarity	NPC111341
0.9524	High Similarity	NPC304207
0.9524	High Similarity	NPC48579
0.9524	High Similarity	NPC217706
0.9524	High Similarity	NPC304745
0.9524	High Similarity	NPC207809
0.9524	High Similarity	NPC259710
0.9517	High Similarity	NPC267117
0.9504	High Similarity	NPC150023
0.95	High Similarity	NPC274784
0.95	High Similarity	NPC265871
0.95	High Similarity	NPC222342
0.95	High Similarity	NPC329203
0.95	High Similarity	NPC225153
0.95	High Similarity	NPC20709
0.95	High Similarity	NPC310135
0.95	High Similarity	NPC150648
0.9459	High Similarity	NPC10754
0.9459	High Similarity	NPC326037
0.9459	High Similarity	NPC215917
0.9459	High Similarity	NPC320825
0.9459	High Similarity	NPC20530
0.9459	High Similarity	NPC13858
0.9456	High Similarity	NPC203080
0.9456	High Similarity	NPC180301
0.9456	High Similarity	NPC244250
0.9456	High Similarity	NPC20907
0.9456	High Similarity	NPC268193
0.9456	High Similarity	NPC248793
0.9452	High Similarity	NPC471229
0.9452	High Similarity	NPC472422
0.9452	High Similarity	NPC471676
0.9452	High Similarity	NPC295650
0.9452	High Similarity	NPC472420
0.9452	High Similarity	NPC244577
0.9452	High Similarity	NPC263384
0.9452	High Similarity	NPC471677
0.9448	High Similarity	NPC472628
0.9444	High Similarity	NPC472627
0.9433	High Similarity	NPC188243
0.9433	High Similarity	NPC6407
0.9433	High Similarity	NPC110228
0.9396	High Similarity	NPC6985
0.9396	High Similarity	NPC52530
0.9388	High Similarity	NPC475790
0.9388	High Similarity	NPC150123
0.9388	High Similarity	NPC244583
0.9388	High Similarity	NPC260491
0.9388	High Similarity	NPC56232
0.9388	High Similarity	NPC240476
0.9388	High Similarity	NPC36835
0.9388	High Similarity	NPC61506
0.9388	High Similarity	NPC161881
0.9388	High Similarity	NPC210597
0.9388	High Similarity	NPC10807
0.9388	High Similarity	NPC246162
0.9388	High Similarity	NPC9743
0.9375	High Similarity	NPC472629
0.9366	High Similarity	NPC312391
0.9366	High Similarity	NPC324386
0.9366	High Similarity	NPC213322
0.9366	High Similarity	NPC4743
0.9362	High Similarity	NPC241838
0.9362	High Similarity	NPC152042
0.9362	High Similarity	NPC143799
0.9362	High Similarity	NPC140890
0.9357	High Similarity	NPC32441
0.9357	High Similarity	NPC295261
0.9357	High Similarity	NPC13768
0.9357	High Similarity	NPC287068
0.9357	High Similarity	NPC12296
0.9357	High Similarity	NPC107586
0.9357	High Similarity	NPC287246
0.9357	High Similarity	NPC79943
0.9357	High Similarity	NPC243083
0.9357	High Similarity	NPC296490
0.9333	High Similarity	NPC22192
0.9329	High Similarity	NPC471500
0.9329	High Similarity	NPC250922
0.9324	High Similarity	NPC209760
0.9324	High Similarity	NPC7989
0.9324	High Similarity	NPC256346
0.9324	High Similarity	NPC27532
0.9324	High Similarity	NPC100134
0.9324	High Similarity	NPC236756
0.9324	High Similarity	NPC223701
0.9324	High Similarity	NPC246328
0.9324	High Similarity	NPC106625
0.9324	High Similarity	NPC325028
0.9324	High Similarity	NPC311579
0.9324	High Similarity	NPC472583
0.932	High Similarity	NPC472636
0.932	High Similarity	NPC209846
0.932	High Similarity	NPC474023
0.932	High Similarity	NPC328740
0.932	High Similarity	NPC289774
0.932	High Similarity	NPC477897
0.932	High Similarity	NPC474021
0.9315	High Similarity	NPC89442
0.9306	High Similarity	NPC470890
0.9306	High Similarity	NPC87486
0.9306	High Similarity	NPC124780
0.9301	High Similarity	NPC66515
0.9301	High Similarity	NPC32739
0.9301	High Similarity	NPC324436
0.9301	High Similarity	NPC177354
0.9301	High Similarity	NPC78
0.9301	High Similarity	NPC328164
0.9301	High Similarity	NPC223500
0.9301	High Similarity	NPC306829
0.9301	High Similarity	NPC125855
0.9301	High Similarity	NPC194432
0.9301	High Similarity	NPC296917
0.9301	High Similarity	NPC64915
0.9301	High Similarity	NPC166934
0.9301	High Similarity	NPC148757
0.9301	High Similarity	NPC73028
0.9301	High Similarity	NPC324134
0.9301	High Similarity	NPC228504
0.9301	High Similarity	NPC10937
0.9301	High Similarity	NPC220998
0.9301	High Similarity	NPC166482
0.9301	High Similarity	NPC182852
0.9301	High Similarity	NPC40833
0.9301	High Similarity	NPC167624
0.9301	High Similarity	NPC107572
0.9301	High Similarity	NPC227579
0.9301	High Similarity	NPC37496
0.9301	High Similarity	NPC265040
0.9301	High Similarity	NPC76338
0.9301	High Similarity	NPC76372
0.9301	High Similarity	NPC1089
0.9301	High Similarity	NPC161506
0.9296	High Similarity	NPC184536
0.9296	High Similarity	NPC76445
0.9296	High Similarity	NPC129853
0.9296	High Similarity	NPC103904
0.9296	High Similarity	NPC59951
0.9296	High Similarity	NPC103342
0.9296	High Similarity	NPC281207
0.9296	High Similarity	NPC146679
0.9296	High Similarity	NPC230285
0.9296	High Similarity	NPC284550
0.9296	High Similarity	NPC269652
0.9291	High Similarity	NPC99333
0.9291	High Similarity	NPC280284
0.9291	High Similarity	NPC147686
0.9291	High Similarity	NPC118813
0.9291	High Similarity	NPC188947
0.9291	High Similarity	NPC329225
0.9291	High Similarity	NPC472460
0.9272	High Similarity	NPC282009
0.9272	High Similarity	NPC287328
0.9272	High Similarity	NPC153342
0.9272	High Similarity	NPC470183
0.9272	High Similarity	NPC263449
0.9267	High Similarity	NPC108831
0.9267	High Similarity	NPC182634
0.9267	High Similarity	NPC471479
0.9267	High Similarity	NPC471515
0.9262	High Similarity	NPC99233
0.9262	High Similarity	NPC477958
0.9262	High Similarity	NPC473241
0.9262	High Similarity	NPC476169
0.9262	High Similarity	NPC471116

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 NPC122828 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	333
0.1-0.2	856
0.2-0.3	1671
0.3-0.4	2609
0.4-0.5	1872
0.5-0.6	1116
0.6-0.7	488
0.7-0.8	151
0.8-0.85	30
0.85-0.9	13
0.9-0.95	11
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9357	High Similarity	NPD1552	Clinical (unspecified phase)
0.9357	High Similarity	NPD1550	Clinical (unspecified phase)
0.9291	High Similarity	NPD1549	Phase 2
0.9257	High Similarity	NPD1934	Approved
0.9172	High Similarity	NPD4378	Clinical (unspecified phase)
0.9139	High Similarity	NPD7075	Discontinued
0.9122	High Similarity	NPD4380	Phase 2
0.9067	High Similarity	NPD7096	Clinical (unspecified phase)
0.9067	High Similarity	NPD2393	Clinical (unspecified phase)
0.9032	High Similarity	NPD6167	Clinical (unspecified phase)
0.9032	High Similarity	NPD6168	Clinical (unspecified phase)
0.9032	High Similarity	NPD6166	Phase 2
0.9013	High Similarity	NPD4381	Clinical (unspecified phase)
0.9	High Similarity	NPD6801	Discontinued
0.8973	High Similarity	NPD6799	Approved
0.8861	High Similarity	NPD7804	Clinical (unspecified phase)
0.8851	High Similarity	NPD1512	Approved
0.8811	High Similarity	NPD1510	Phase 2
0.8794	High Similarity	NPD1240	Approved
0.875	High Similarity	NPD2796	Approved
0.8742	High Similarity	NPD6599	Discontinued
0.8716	High Similarity	NPD1511	Approved
0.8701	High Similarity	NPD3882	Suspended
0.8693	High Similarity	NPD2801	Approved
0.8671	High Similarity	NPD1607	Approved
0.8667	High Similarity	NPD5403	Approved
0.8658	High Similarity	NPD5401	Approved
0.8636	High Similarity	NPD8443	Clinical (unspecified phase)
0.8636	High Similarity	NPD3817	Phase 2
0.8634	High Similarity	NPD6797	Phase 2
0.858	High Similarity	NPD7251	Discontinued
0.8571	High Similarity	NPD7074	Phase 3
0.8562	High Similarity	NPD7411	Suspended
0.8533	High Similarity	NPD7410	Clinical (unspecified phase)
0.8528	High Similarity	NPD7808	Phase 3
0.8509	High Similarity	NPD7054	Approved
0.8457	Intermediate Similarity	NPD7472	Approved
0.8447	Intermediate Similarity	NPD3818	Discontinued
0.8415	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8397	Intermediate Similarity	NPD5402	Approved
0.8344	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8333	Intermediate Similarity	NPD7819	Suspended
0.825	Intermediate Similarity	NPD6959	Discontinued
0.8242	Intermediate Similarity	NPD6559	Discontinued
0.8187	Intermediate Similarity	NPD5494	Approved
0.8182	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8146	Intermediate Similarity	NPD3750	Approved
0.8146	Intermediate Similarity	NPD4628	Phase 3
0.8138	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.8121	Intermediate Similarity	NPD1551	Phase 2
0.8098	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8079	Intermediate Similarity	NPD2800	Approved
0.8079	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.8063	Intermediate Similarity	NPD3749	Approved
0.8027	Intermediate Similarity	NPD1613	Approved
0.8027	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.8014	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.8013	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD7768	Phase 2
0.7952	Intermediate Similarity	NPD5844	Phase 1
0.7908	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7892	Intermediate Similarity	NPD3751	Discontinued
0.7891	Intermediate Similarity	NPD6798	Discontinued
0.7866	Intermediate Similarity	NPD6232	Discontinued
0.7841	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7834	Intermediate Similarity	NPD920	Approved
0.7831	Intermediate Similarity	NPD7473	Discontinued
0.7829	Intermediate Similarity	NPD2344	Approved
0.7815	Intermediate Similarity	NPD7033	Discontinued
0.7815	Intermediate Similarity	NPD3748	Approved
0.7805	Intermediate Similarity	NPD1247	Approved
0.78	Intermediate Similarity	NPD6651	Approved
0.7793	Intermediate Similarity	NPD1203	Approved
0.7791	Intermediate Similarity	NPD919	Approved
0.7785	Intermediate Similarity	NPD943	Approved
0.7765	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7764	Intermediate Similarity	NPD1465	Phase 2
0.7763	Intermediate Similarity	NPD2935	Discontinued
0.7762	Intermediate Similarity	NPD1610	Phase 2
0.7758	Intermediate Similarity	NPD3787	Discontinued
0.7755	Intermediate Similarity	NPD4908	Phase 1
0.7755	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7738	Intermediate Similarity	NPD7286	Phase 2
0.773	Intermediate Similarity	NPD1548	Phase 1
0.7727	Intermediate Similarity	NPD1243	Approved
0.7718	Intermediate Similarity	NPD6233	Phase 2
0.7714	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7711	Intermediate Similarity	NPD3926	Phase 2
0.7707	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7707	Intermediate Similarity	NPD2533	Approved
0.7707	Intermediate Similarity	NPD2534	Approved
0.7707	Intermediate Similarity	NPD2532	Approved
0.7692	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7687	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7651	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7651	Intermediate Similarity	NPD2313	Discontinued
0.7647	Intermediate Similarity	NPD6099	Approved
0.7647	Intermediate Similarity	NPD6100	Approved
0.7647	Intermediate Similarity	NPD5953	Discontinued
0.7635	Intermediate Similarity	NPD6832	Phase 2
0.7628	Intermediate Similarity	NPD2309	Approved
0.7627	Intermediate Similarity	NPD4360	Phase 2
0.7627	Intermediate Similarity	NPD4363	Phase 3
0.7616	Intermediate Similarity	NPD1933	Approved
0.7616	Intermediate Similarity	NPD6355	Discontinued
0.7613	Intermediate Similarity	NPD1652	Phase 2
0.7586	Intermediate Similarity	NPD9717	Approved
0.7584	Intermediate Similarity	NPD3027	Phase 3
0.7582	Intermediate Similarity	NPD2799	Discontinued
0.7533	Intermediate Similarity	NPD3268	Approved
0.7531	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7517	Intermediate Similarity	NPD422	Phase 1
0.7516	Intermediate Similarity	NPD2354	Approved
0.7516	Intermediate Similarity	NPD3226	Approved
0.75	Intermediate Similarity	NPD5124	Phase 1
0.75	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD230	Phase 1
0.7486	Intermediate Similarity	NPD8434	Phase 2
0.7484	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD4661	Approved
0.7484	Intermediate Similarity	NPD4662	Approved
0.7484	Intermediate Similarity	NPD2346	Discontinued
0.7468	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7459	Intermediate Similarity	NPD7584	Approved
0.7456	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7436	Intermediate Similarity	NPD2424	Discontinued
0.7432	Intermediate Similarity	NPD2797	Approved
0.7418	Intermediate Similarity	NPD6779	Approved
0.7418	Intermediate Similarity	NPD6782	Approved
0.7418	Intermediate Similarity	NPD6778	Approved
0.7418	Intermediate Similarity	NPD6776	Approved
0.7418	Intermediate Similarity	NPD6777	Approved
0.7418	Intermediate Similarity	NPD6780	Approved
0.7418	Intermediate Similarity	NPD6781	Approved
0.7414	Intermediate Similarity	NPD8313	Approved
0.7414	Intermediate Similarity	NPD8312	Approved
0.7405	Intermediate Similarity	NPD6190	Approved
0.7405	Intermediate Similarity	NPD3887	Approved
0.7396	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7389	Intermediate Similarity	NPD2654	Approved
0.7386	Intermediate Similarity	NPD447	Suspended
0.7386	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7383	Intermediate Similarity	NPD2798	Approved
0.7381	Intermediate Similarity	NPD7199	Phase 2
0.7368	Intermediate Similarity	NPD4062	Phase 3
0.7365	Intermediate Similarity	NPD3225	Approved
0.7361	Intermediate Similarity	NPD9545	Approved
0.7355	Intermediate Similarity	NPD4308	Phase 3
0.7353	Intermediate Similarity	NPD2403	Approved
0.7342	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD8455	Phase 2
0.7315	Intermediate Similarity	NPD3266	Approved
0.7315	Intermediate Similarity	NPD3267	Approved
0.7312	Intermediate Similarity	NPD7390	Discontinued
0.7297	Intermediate Similarity	NPD7435	Discontinued
0.7293	Intermediate Similarity	NPD4361	Phase 2
0.7293	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7288	Intermediate Similarity	NPD8150	Discontinued
0.7279	Intermediate Similarity	NPD1091	Approved
0.7273	Intermediate Similarity	NPD6844	Discontinued
0.7267	Intermediate Similarity	NPD1019	Discontinued
0.7261	Intermediate Similarity	NPD2355	Clinical (unspecified phase)
0.7261	Intermediate Similarity	NPD2353	Approved
0.7254	Intermediate Similarity	NPD1241	Discontinued
0.7251	Intermediate Similarity	NPD4575	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD3823	Discontinued
0.7239	Intermediate Similarity	NPD1653	Approved
0.7235	Intermediate Similarity	NPD5710	Approved
0.7235	Intermediate Similarity	NPD5711	Approved
0.7232	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.723	Intermediate Similarity	NPD1608	Approved
0.723	Intermediate Similarity	NPD3972	Approved
0.7228	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD5049	Phase 3
0.7222	Intermediate Similarity	NPD9493	Approved
0.7219	Intermediate Similarity	NPD2861	Phase 2
0.7208	Intermediate Similarity	NPD4060	Phase 1
0.7205	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7204	Intermediate Similarity	NPD7697	Approved
0.7204	Intermediate Similarity	NPD7698	Approved
0.7204	Intermediate Similarity	NPD7696	Phase 3
0.72	Intermediate Similarity	NPD6104	Discontinued
0.7195	Intermediate Similarity	NPD7458	Discontinued
0.7195	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD1296	Phase 2
0.7186	Intermediate Similarity	NPD4288	Approved
0.7184	Intermediate Similarity	NPD1729	Discontinued
0.7169	Intermediate Similarity	NPD37	Approved
0.7166	Intermediate Similarity	NPD7871	Phase 2
0.7166	Intermediate Similarity	NPD7870	Phase 2
0.7161	Intermediate Similarity	NPD4340	Discontinued
0.716	Intermediate Similarity	NPD6234	Discontinued
0.7152	Intermediate Similarity	NPD1471	Phase 3
0.7143	Intermediate Similarity	NPD4966	Approved
0.7143	Intermediate Similarity	NPD6534	Approved
0.7143	Intermediate Similarity	NPD4965	Approved
0.7143	Intermediate Similarity	NPD7701	Phase 2
0.7143	Intermediate Similarity	NPD6535	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