NPASS Compound

Structure

CID130193 OpenBabel06191715492D 23 24 0 0 0 0 0 0 0 0999 V2000 -8.6603 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 1.5000 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 -1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 -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 -9.5263 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.6603 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 -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 -5.1962 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 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 -9.5263 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.3923 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 7 1 0 0 0 0 1 14 2 0 0 0 0 2 8 2 0 0 0 0 2 14 1 0 0 0 0 3 9 1 0 0 0 0 3 15 2 0 0 0 0 4 10 2 0 0 0 0 4 15 1 0 0 0 0 5 11 2 0 0 0 0 5 14 1 0 0 0 0 6 12 2 0 0 0 0 6 15 1 0 0 0 0 7 16 2 0 0 0 0 8 16 1 0 0 0 0 9 17 2 0 0 0 0 10 17 1 0 0 0 0 11 18 1 0 0 0 0 12 19 1 0 0 0 0 13 18 2 0 0 0 0 13 19 1 0 0 0 0 16 20 1 0 0 0 0 17 21 1 0 0 0 0 18 22 1 0 0 0 0 19 23 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	308.1
Volume:	328.864
LogP:	2.847
LogD:	2.917
LogS:	-3.427
# Rotatable Bonds:	6
TPSA:	74.6
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.634
Synthetic Accessibility Score:	2.301
Fsp3:	0.053
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.715
MDCK Permeability:	1.5659381460864097e-05
Pgp-inhibitor:	0.174
Pgp-substrate:	0.076
Human Intestinal Absorption (HIA):	0.017
20% Bioavailability (F20%):	0.001
30% Bioavailability (F30%):	0.008

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.107
Plasma Protein Binding (PPB):	99.2865219116211%
Volume Distribution (VD):	0.311
Pgp-substrate:	0.5844783782958984%

ADMET: Metabolism

CYP1A2-inhibitor:	0.819
CYP1A2-substrate:	0.049
CYP2C19-inhibitor:	0.57
CYP2C19-substrate:	0.059
CYP2C9-inhibitor:	0.774
CYP2C9-substrate:	0.965
CYP2D6-inhibitor:	0.017
CYP2D6-substrate:	0.879
CYP3A4-inhibitor:	0.583
CYP3A4-substrate:	0.299

ADMET: Excretion

Clearance (CL):	15.98
Half-life (T1/2):	0.941

ADMET: Toxicity

hERG Blockers:	0.23
Human Hepatotoxicity (H-HT):	0.391
Drug-inuced Liver Injury (DILI):	0.843
AMES Toxicity:	0.613
Rat Oral Acute Toxicity:	0.834
Maximum Recommended Daily Dose:	0.336
Skin Sensitization:	0.967
Carcinogencity:	0.457
Eye Corrosion:	0.01
Eye Irritation:	0.92
Respiratory Toxicity:	0.843

Download Data

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

Natural Product: NPC130193

Natural Product ID:	NPC130193
*Common Name:**	(1E,4Z,6E)-5-Hydroxy-1,7-Bis(4-Hydroxyphenyl)Hepta-1,4,6-Trien-3-One
IUPAC Name:	(1E,4Z,6E)-5-hydroxy-1,7-bis(4-hydroxyphenyl)hepta-1,4,6-trien-3-one
Synonyms:
Standard InCHIKey:	YXAKCQIIROBKOP-HSSGTREWSA-N
Standard InCHI:	InChI=1S/C19H16O4/c20-16-7-1-14(2-8-16)5-11-18(22)13-19(23)12-6-15-3-9-17(21)10-4-15/h1-13,20-22H/b11-5+,12-6+,18-13-
SMILES:	O/C(=CC(=O)/C=C/c1ccc(cc1)O)/C=C/c1ccc(cc1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL131770
PubChem CID:	5324473
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0002650] Diarylheptanoids [CHEMONTID:0002651] Linear diarylheptanoids [CHEMONTID:0000356] Curcuminoids

*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
NPO24124	Curcuma longa	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12350137]
NPO24124	Curcuma longa	Species	Zingiberaceae	Eukaryota	rhizome	n.a.	n.a.	PMID[12617587]
NPO23911	Alpinia officinarum	Species	Zingiberaceae	Eukaryota	n.a.	root	n.a.	PMID[18484537]
NPO23911	Alpinia officinarum	Species	Zingiberaceae	Eukaryota	n.a.	rhizome	n.a.	PMID[18484537]
NPO23911	Alpinia officinarum	Species	Zingiberaceae	Eukaryota	rhizomes	n.a.	n.a.	PMID[19615910]
NPO24124	Curcuma longa	Species	Zingiberaceae	Eukaryota	Rhizomes	n.a.	n.a.	PMID[23153397]
NPO2618	Curcuma wenyujin	Species	Zingiberaceae	Eukaryota	n.a.	rhizome	n.a.	PMID[23738470]
NPO2618	Curcuma wenyujin	Species	Zingiberaceae	Eukaryota	n.a.	root	n.a.	PMID[23738470]
NPO24124	Curcuma longa	Species	Zingiberaceae	Eukaryota	n.a.	leaf	n.a.	PMID[23901173]
NPO2618	Curcuma wenyujin	Species	Zingiberaceae	Eukaryota	Rhizomes	n.a.	n.a.	PMID[25275213]
NPO24124	Curcuma longa	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[28068085]
NPO25209	Curcuma aromatica	Species	Zingiberaceae	Eukaryota	Radix	n.a.	n.a.	PMID[29236488]
NPO23911	Alpinia officinarum	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[29323912]
NPO23911	Alpinia officinarum	Species	Zingiberaceae	Eukaryota	n.a.	root	n.a.	PMID[731398]
NPO23911	Alpinia officinarum	Species	Zingiberaceae	Eukaryota	n.a.	rhizome	n.a.	PMID[731398]
NPO24124	Curcuma longa	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9584408]
NPO7929	Curcuma zedoaria	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9868158]
NPO24124	Curcuma longa	Species	Zingiberaceae	Eukaryota	Essential Oil	n.a.	n.a.	Database[FooDB]
NPO24124	Curcuma longa	Species	Zingiberaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO24124	Curcuma longa	Species	Zingiberaceae	Eukaryota	Rhizome	n.a.	n.a.	Database[FooDB]
NPO24124	Curcuma longa	Species	Zingiberaceae	Eukaryota	Rhizome Essent. Oil	n.a.	n.a.	Database[FooDB]
NPO24124	Curcuma longa	Species	Zingiberaceae	Eukaryota	Root	n.a.	n.a.	Database[FooDB]
NPO24124	Curcuma longa	Species	Zingiberaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO24124	Curcuma longa	Species	Zingiberaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO25209	Curcuma aromatica	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO23911	Alpinia officinarum	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO24124	Curcuma longa	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7929	Curcuma zedoaria	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO24124	Curcuma longa	Species	Zingiberaceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO23911	Alpinia officinarum	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7929	Curcuma zedoaria	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24124	Curcuma longa	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25209	Curcuma aromatica	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23911	Alpinia officinarum	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO7929	Curcuma zedoaria	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO2618	Curcuma wenyujin	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO25209	Curcuma aromatica	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO24124	Curcuma longa	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO23911	Alpinia officinarum	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO2618	Curcuma wenyujin	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO7929	Curcuma zedoaria	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO24124	Curcuma longa	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO24124	Curcuma longa	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25209	Curcuma aromatica	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7929	Curcuma zedoaria	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23911	Alpinia officinarum	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2618	Curcuma wenyujin	Species	Zingiberaceae	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	6
Others	2
Potency	25

Activity Type	# Activity
Cell Line	1
Individual Protein	23
Organism	1
Others	7
PROTEIN COMPLEX	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT226	Individual Protein	Beta-2 adrenergic receptor	Homo sapiens	Potency	n.a.	25929.0	nM	PMID[470397]
NPT1005	Individual Protein	Tumor susceptibility gene 101 protein	Homo sapiens	Potency	n.a.	44668.4	nM	PMID[470397]
NPT4252	Individual Protein	Toll-like receptor 9	Homo sapiens	IC50	=	9767.0	nM	PMID[470397]
NPT135	Individual Protein	Chromobox protein homolog 1	Homo sapiens	Potency	n.a.	56234.1	nM	PMID[470397]
NPT154	Individual Protein	Mothers against decapentaplegic homolog 3	Homo sapiens	Potency	n.a.	25118.9	nM	PMID[470397]
NPT1161	Cell Line	CHO	Cricetulus griseus	IC50	=	40050.0	nM	PMID[470397]
NPT4253	Individual Protein	Beta Lactamase	Pseudomonas aeruginosa	IC50	=	5133.0	nM	PMID[470397]
NPT2971	Individual Protein	DNA dC->dU-editing enzyme APOBEC-3F	Homo sapiens	Potency	n.a.	31622.8	nM	PMID[470397]
NPT10	Individual Protein	Geminin	Homo sapiens	Potency	n.a.	25929.0	nM	PMID[470397]
NPT477	Individual Protein	DNA dC->dU-editing enzyme APOBEC-3G	Homo sapiens	Potency	n.a.	35481.3	nM	PMID[470397]
NPT100	Individual Protein	Glutaminase kidney isoform, mitochondrial	Homo sapiens	Potency	n.a.	22387.2	nM	PMID[470397]
NPT10	Individual Protein	Geminin	Homo sapiens	Potency	n.a.	29092.9	nM	PMID[470397]
NPT152	Individual Protein	Nuclear factor erythroid 2-related factor 2	Homo sapiens	Potency	n.a.	31622.8	nM	PMID[470397]
NPT1417	Individual Protein	Transcriptional regulator ERG	Homo sapiens	Potency	n.a.	3548.1	nM	PMID[470397]
NPT50	Individual Protein	Tyrosyl-DNA phosphodiesterase 1	Homo sapiens	Potency	n.a.	23109.3	nM	PMID[470397]
NPT50	Individual Protein	Tyrosyl-DNA phosphodiesterase 1	Homo sapiens	Potency	n.a.	29092.9	nM	PMID[470397]
NPT161	Individual Protein	Rap guanine nucleotide exchange factor 4	Homo sapiens	Potency	n.a.	14125.4	nM	PMID[470397]
NPT444	Individual Protein	Ubiquitin carboxyl-terminal hydrolase 1	Homo sapiens	Potency	n.a.	28183.8	nM	PMID[470397]
NPT161	Individual Protein	Rap guanine nucleotide exchange factor 4	Homo sapiens	Potency	n.a.	31622.8	nM	PMID[470397]
NPT591	Individual Protein	Glycogen synthase kinase-3 beta	Homo sapiens	IC50	=	8390.0	nM	PMID[470399]
NPT2	Others	Unspecified		Potency	=	8199.5	nM	PMID[470397]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	Potency	n.a.	4147.5	nM	PMID[470397]
NPT20798	PROTEIN COMPLEX	GTP-binding nuclear protein Ran/Importin subunit beta-1/Snurportin-1	Homo sapiens	Potency	n.a.	31622.8	nM	PMID[470397]
NPT2	Others	Unspecified		Potency	n.a.	10000.0	nM	PMID[470397]
NPT2	Others	Unspecified		Potency	n.a.	11220.2	nM	PMID[470397]
NPT755	Individual Protein	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	Homo sapiens	Potency	n.a.	25118.9	nM	PMID[470397]
NPT740	Individual Protein	Beta-secretase 1	Homo sapiens	Inhibition	=	9.0	%	PMID[470398]
NPT2	Others	Unspecified		Potency	n.a.	15848.9	nM	PMID[470397]
NPT831	Individual Protein	Serine/threonine-protein kinase PLK1	Homo sapiens	Potency	n.a.	2667.9	nM	PMID[470397]
NPT740	Individual Protein	Beta-secretase 1	Homo sapiens	IC50	=	2540.0	nM	PMID[470399]
NPT27	Others	Unspecified		permeability	=	7.8	ucm/s	PMID[470399]
NPT2	Others	Unspecified		IC50	>	50000.0	nM	PMID[470400]

☑ 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 NPC130193 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	243
0.1-0.2	2165
0.2-0.3	5689
0.3-0.4	12921
0.4-0.5	5349
0.5-0.6	9510
0.6-0.7	5623
0.7-0.8	1040
0.8-0.85	100
0.85-0.9	44
0.9-0.95	10
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9891	High Similarity	NPC201967
0.9684	High Similarity	NPC68269
0.9278	High Similarity	NPC135784
0.9247	High Similarity	NPC181709
0.9192	High Similarity	NPC29989
0.9192	High Similarity	NPC70843
0.9192	High Similarity	NPC95178
0.9192	High Similarity	NPC69332
0.9109	High Similarity	NPC88141
0.8947	High Similarity	NPC32977
0.8947	High Similarity	NPC81010
0.8947	High Similarity	NPC151715
0.8932	High Similarity	NPC297657
0.8911	High Similarity	NPC260952
0.8854	High Similarity	NPC26244
0.8854	High Similarity	NPC286006
0.8846	High Similarity	NPC51698
0.8835	High Similarity	NPC116842
0.8835	High Similarity	NPC183700
0.8812	High Similarity	NPC188677
0.88	High Similarity	NPC120693
0.88	High Similarity	NPC261573
0.88	High Similarity	NPC8931
0.8788	High Similarity	NPC472585
0.8763	High Similarity	NPC292730
0.8763	High Similarity	NPC473388
0.8763	High Similarity	NPC132271
0.8763	High Similarity	NPC216520
0.8763	High Similarity	NPC82664
0.8737	High Similarity	NPC45040
0.8679	High Similarity	NPC285350
0.8654	High Similarity	NPC222905
0.8654	High Similarity	NPC21162
0.8641	High Similarity	NPC17525
0.8641	High Similarity	NPC206341
0.86	High Similarity	NPC91461
0.86	High Similarity	NPC7686
0.86	High Similarity	NPC40258
0.8598	High Similarity	NPC23402
0.8587	High Similarity	NPC265146
0.8586	High Similarity	NPC51333
0.8586	High Similarity	NPC78119
0.8586	High Similarity	NPC132078
0.8586	High Similarity	NPC216468
0.8571	High Similarity	NPC470355
0.8558	High Similarity	NPC79543
0.8557	High Similarity	NPC128062
0.8542	High Similarity	NPC270547
0.8526	High Similarity	NPC98772
0.8526	High Similarity	NPC177420
0.8526	High Similarity	NPC280347
0.8519	High Similarity	NPC61062
0.8519	High Similarity	NPC299252
0.8519	High Similarity	NPC277394
0.8511	High Similarity	NPC184169
0.85	High Similarity	NPC253746
0.85	High Similarity	NPC213730
0.8495	Intermediate Similarity	NPC248817
0.8495	Intermediate Similarity	NPC175313
0.8491	Intermediate Similarity	NPC228988
0.8485	Intermediate Similarity	NPC140619
0.8469	Intermediate Similarity	NPC274678
0.8469	Intermediate Similarity	NPC257182
0.8469	Intermediate Similarity	NPC246679
0.8438	Intermediate Similarity	NPC55561
0.8431	Intermediate Similarity	NPC52087
0.8431	Intermediate Similarity	NPC79672
0.8426	Intermediate Similarity	NPC322197
0.8421	Intermediate Similarity	NPC104216
0.8421	Intermediate Similarity	NPC25493
0.8421	Intermediate Similarity	NPC113460
0.8404	Intermediate Similarity	NPC197783
0.84	Intermediate Similarity	NPC92730
0.8396	Intermediate Similarity	NPC268388
0.8396	Intermediate Similarity	NPC177576
0.8387	Intermediate Similarity	NPC124436
0.8384	Intermediate Similarity	NPC283711
0.8367	Intermediate Similarity	NPC76938
0.8365	Intermediate Similarity	NPC141523
0.835	Intermediate Similarity	NPC127676
0.835	Intermediate Similarity	NPC243677
0.835	Intermediate Similarity	NPC303141
0.8349	Intermediate Similarity	NPC19290
0.8333	Intermediate Similarity	NPC242240
0.8333	Intermediate Similarity	NPC318325
0.8333	Intermediate Similarity	NPC304638
0.8333	Intermediate Similarity	NPC123273
0.8333	Intermediate Similarity	NPC470202
0.8333	Intermediate Similarity	NPC168829
0.8317	Intermediate Similarity	NPC223393
0.8316	Intermediate Similarity	NPC23167
0.8302	Intermediate Similarity	NPC321252
0.8302	Intermediate Similarity	NPC63345
0.8302	Intermediate Similarity	NPC252544
0.83	Intermediate Similarity	NPC260000
0.83	Intermediate Similarity	NPC225464
0.8283	Intermediate Similarity	NPC32714
0.8269	Intermediate Similarity	NPC1075
0.8269	Intermediate Similarity	NPC6984
0.8269	Intermediate Similarity	NPC1786
0.8269	Intermediate Similarity	NPC294902
0.8252	Intermediate Similarity	NPC288411
0.8247	Intermediate Similarity	NPC300017
0.8218	Intermediate Similarity	NPC280869
0.8218	Intermediate Similarity	NPC275104
0.8208	Intermediate Similarity	NPC95172
0.8198	Intermediate Similarity	NPC249435
0.819	Intermediate Similarity	NPC226699
0.8173	Intermediate Similarity	NPC138942
0.8173	Intermediate Similarity	NPC154899
0.8173	Intermediate Similarity	NPC474839
0.8173	Intermediate Similarity	NPC233396
0.8148	Intermediate Similarity	NPC286222
0.8144	Intermediate Similarity	NPC258219
0.8142	Intermediate Similarity	NPC60962
0.8142	Intermediate Similarity	NPC269843
0.8142	Intermediate Similarity	NPC109083
0.8142	Intermediate Similarity	NPC189844
0.8142	Intermediate Similarity	NPC14007
0.8142	Intermediate Similarity	NPC224814
0.8137	Intermediate Similarity	NPC161571
0.8137	Intermediate Similarity	NPC248573
0.8137	Intermediate Similarity	NPC294741
0.8137	Intermediate Similarity	NPC275053
0.8125	Intermediate Similarity	NPC141791
0.8125	Intermediate Similarity	NPC263386
0.8119	Intermediate Similarity	NPC32674
0.8113	Intermediate Similarity	NPC470039
0.8108	Intermediate Similarity	NPC278652
0.8108	Intermediate Similarity	NPC280001
0.8095	Intermediate Similarity	NPC19149
0.8095	Intermediate Similarity	NPC92623
0.8095	Intermediate Similarity	NPC113457
0.8095	Intermediate Similarity	NPC135464
0.8091	Intermediate Similarity	NPC296526
0.8081	Intermediate Similarity	NPC138117
0.8081	Intermediate Similarity	NPC325292
0.8081	Intermediate Similarity	NPC271440
0.8077	Intermediate Similarity	NPC119860
0.8077	Intermediate Similarity	NPC471511
0.8077	Intermediate Similarity	NPC323810
0.8077	Intermediate Similarity	NPC93831
0.8061	Intermediate Similarity	NPC300478
0.8061	Intermediate Similarity	NPC192
0.8058	Intermediate Similarity	NPC94343
0.8056	Intermediate Similarity	NPC139946
0.8039	Intermediate Similarity	NPC245561
0.8039	Intermediate Similarity	NPC171843
0.8037	Intermediate Similarity	NPC471954
0.8037	Intermediate Similarity	NPC75272
0.8037	Intermediate Similarity	NPC254833
0.8037	Intermediate Similarity	NPC228343
0.8036	Intermediate Similarity	NPC275519
0.8021	Intermediate Similarity	NPC155393
0.8018	Intermediate Similarity	NPC128249
0.8018	Intermediate Similarity	NPC325646
0.8018	Intermediate Similarity	NPC28951
0.8	Intermediate Similarity	NPC292452
0.8	Intermediate Similarity	NPC316301
0.8	Intermediate Similarity	NPC27323
0.8	Intermediate Similarity	NPC86900
0.8	Intermediate Similarity	NPC13495
0.7982	Intermediate Similarity	NPC71870
0.7982	Intermediate Similarity	NPC470849
0.7982	Intermediate Similarity	NPC470848
0.798	Intermediate Similarity	NPC155908
0.798	Intermediate Similarity	NPC304541
0.798	Intermediate Similarity	NPC204210
0.7965	Intermediate Similarity	NPC158222
0.7963	Intermediate Similarity	NPC226401
0.7963	Intermediate Similarity	NPC79793
0.7963	Intermediate Similarity	NPC174096
0.7963	Intermediate Similarity	NPC120982
0.7963	Intermediate Similarity	NPC475018
0.7963	Intermediate Similarity	NPC147634
0.7963	Intermediate Similarity	NPC44732
0.7963	Intermediate Similarity	NPC471535
0.7961	Intermediate Similarity	NPC52472
0.7944	Intermediate Similarity	NPC317305
0.7944	Intermediate Similarity	NPC63698
0.7944	Intermediate Similarity	NPC262365
0.7944	Intermediate Similarity	NPC11554
0.7944	Intermediate Similarity	NPC24101
0.7944	Intermediate Similarity	NPC61885
0.7944	Intermediate Similarity	NPC201959
0.7944	Intermediate Similarity	NPC96224
0.7941	Intermediate Similarity	NPC291789
0.7941	Intermediate Similarity	NPC175298
0.7938	Intermediate Similarity	NPC407
0.7938	Intermediate Similarity	NPC307235
0.7931	Intermediate Similarity	NPC106659
0.7931	Intermediate Similarity	NPC160900
0.7931	Intermediate Similarity	NPC18984
0.7931	Intermediate Similarity	NPC229084
0.7925	Intermediate Similarity	NPC118286
0.7925	Intermediate Similarity	NPC109691
0.7925	Intermediate Similarity	NPC271274
0.7925	Intermediate Similarity	NPC39664
0.7925	Intermediate Similarity	NPC39097
0.7925	Intermediate Similarity	NPC470700

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 NPC130193 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	213
0.1-0.2	1101
0.2-0.3	1101
0.3-0.4	2952
0.4-0.5	2156
0.5-0.6	1171
0.6-0.7	396
0.7-0.8	53
0.8-0.85	2
0.85-0.9	5
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8947	High Similarity	NPD2934	Approved
0.8947	High Similarity	NPD2933	Approved
0.8854	High Similarity	NPD2859	Approved
0.8854	High Similarity	NPD2860	Approved
0.8586	High Similarity	NPD3020	Approved
0.8387	Intermediate Similarity	NPD111	Approved
0.8137	Intermediate Similarity	NPD1242	Phase 1
0.8037	Intermediate Similarity	NPD3021	Approved
0.8037	Intermediate Similarity	NPD3022	Approved
0.8	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.7961	Intermediate Similarity	NPD3028	Approved
0.7931	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7714	Intermediate Similarity	NPD846	Approved
0.7714	Intermediate Similarity	NPD940	Approved
0.7685	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7632	Intermediate Similarity	NPD5536	Phase 2
0.7593	Intermediate Similarity	NPD3134	Approved
0.7573	Intermediate Similarity	NPD1809	Phase 2
0.7573	Intermediate Similarity	NPD844	Approved
0.7549	Intermediate Similarity	NPD845	Approved
0.7523	Intermediate Similarity	NPD1358	Approved
0.7436	Intermediate Similarity	NPD2932	Approved
0.7436	Intermediate Similarity	NPD3019	Approved
0.7434	Intermediate Similarity	NPD2228	Approved
0.7434	Intermediate Similarity	NPD2229	Approved
0.7434	Intermediate Similarity	NPD2234	Approved
0.7431	Intermediate Similarity	NPD968	Approved
0.7391	Intermediate Similarity	NPD9087	Approved
0.735	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7345	Intermediate Similarity	NPD5535	Approved
0.7333	Intermediate Similarity	NPD288	Approved
0.7297	Intermediate Similarity	NPD9266	Approved
0.7297	Intermediate Similarity	NPD74	Approved
0.729	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.7265	Intermediate Similarity	NPD9545	Approved
0.7263	Intermediate Similarity	NPD9088	Approved
0.7248	Intermediate Similarity	NPD1237	Approved
0.7248	Intermediate Similarity	NPD9608	Approved
0.7248	Intermediate Similarity	NPD9610	Approved
0.7241	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7227	Intermediate Similarity	NPD3847	Discontinued
0.7213	Intermediate Similarity	NPD1164	Approved
0.7213	Intermediate Similarity	NPD1470	Approved
0.7207	Intermediate Similarity	NPD2342	Discontinued
0.7207	Intermediate Similarity	NPD9264	Approved
0.7207	Intermediate Similarity	NPD9267	Approved
0.7207	Intermediate Similarity	NPD9263	Approved
0.72	Intermediate Similarity	NPD3764	Approved
0.7193	Intermediate Similarity	NPD7635	Approved
0.7167	Intermediate Similarity	NPD1535	Discovery
0.7167	Intermediate Similarity	NPD1201	Approved
0.7143	Intermediate Similarity	NPD5238	Clinical (unspecified phase)
0.713	Intermediate Similarity	NPD1241	Discontinued
0.7119	Intermediate Similarity	NPD3091	Approved
0.7119	Intermediate Similarity	NPD5304	Approved
0.7119	Intermediate Similarity	NPD5303	Approved
0.7107	Intermediate Similarity	NPD3972	Approved
0.7107	Intermediate Similarity	NPD1481	Phase 2
0.7105	Intermediate Similarity	NPD6124	Clinical (unspecified phase)
0.7103	Intermediate Similarity	NPD9273	Approved
0.7094	Intermediate Similarity	NPD9493	Approved
0.7087	Intermediate Similarity	NPD943	Approved
0.7083	Intermediate Similarity	NPD3421	Phase 3
0.708	Intermediate Similarity	NPD4750	Phase 3
0.708	Intermediate Similarity	NPD1792	Phase 2
0.708	Intermediate Similarity	NPD5451	Approved
0.708	Intermediate Similarity	NPD9380	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD1203	Approved
0.7059	Intermediate Similarity	NPD4093	Discontinued
0.7049	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD1202	Approved
0.7027	Intermediate Similarity	NPD9697	Approved
0.7025	Intermediate Similarity	NPD422	Phase 1
0.7009	Intermediate Similarity	NPD256	Approved
0.7009	Intermediate Similarity	NPD255	Approved
0.7	Intermediate Similarity	NPD4059	Approved
0.7	Intermediate Similarity	NPD2286	Discontinued
0.7	Intermediate Similarity	NPD4626	Approved
0.7	Intermediate Similarity	NPD4589	Approved
0.6992	Remote Similarity	NPD3225	Approved
0.6991	Remote Similarity	NPD2684	Approved
0.6983	Remote Similarity	NPD7159	Clinical (unspecified phase)
0.6983	Remote Similarity	NPD5283	Phase 1
0.6979	Remote Similarity	NPD9294	Approved
0.6975	Remote Similarity	NPD1548	Phase 1
0.6975	Remote Similarity	NPD1894	Discontinued
0.697	Remote Similarity	NPD9089	Approved
0.6967	Remote Similarity	NPD2561	Approved
0.6967	Remote Similarity	NPD2562	Approved
0.6964	Remote Similarity	NPD1444	Approved
0.6964	Remote Similarity	NPD1445	Approved
0.6957	Remote Similarity	NPD228	Approved
0.6953	Remote Similarity	NPD1240	Approved
0.6949	Remote Similarity	NPD9568	Approved
0.6947	Remote Similarity	NPD2935	Discontinued
0.6947	Remote Similarity	NPD9716	Approved
0.6942	Remote Similarity	NPD3023	Approved
0.6942	Remote Similarity	NPD3026	Approved
0.6935	Remote Similarity	NPD4339	Clinical (unspecified phase)
0.6935	Remote Similarity	NPD2797	Approved
0.6929	Remote Similarity	NPD3268	Approved
0.6923	Remote Similarity	NPD9258	Approved
0.6923	Remote Similarity	NPD1476	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD9256	Approved
0.6923	Remote Similarity	NPD9281	Approved
0.6917	Remote Similarity	NPD3025	Approved
0.6917	Remote Similarity	NPD3024	Approved
0.6911	Remote Similarity	NPD6583	Phase 3
0.6911	Remote Similarity	NPD4659	Approved
0.6911	Remote Similarity	NPD6582	Phase 2
0.69	Remote Similarity	NPD3971	Phase 1
0.6897	Remote Similarity	NPD9379	Approved
0.6897	Remote Similarity	NPD9377	Approved
0.6897	Remote Similarity	NPD7843	Approved
0.6894	Remote Similarity	NPD7266	Discontinued
0.6885	Remote Similarity	NPD3092	Approved
0.6881	Remote Similarity	NPD2066	Phase 3
0.688	Remote Similarity	NPD7451	Discontinued
0.688	Remote Similarity	NPD2798	Approved
0.687	Remote Similarity	NPD2799	Discontinued
0.687	Remote Similarity	NPD1510	Phase 2
0.687	Remote Similarity	NPD9280	Clinical (unspecified phase)
0.6869	Remote Similarity	NPD9093	Approved
0.6864	Remote Similarity	NPD6671	Approved
0.686	Remote Similarity	NPD3095	Discontinued
0.6855	Remote Similarity	NPD1876	Approved
0.6855	Remote Similarity	NPD5311	Approved
0.6855	Remote Similarity	NPD5310	Approved
0.6847	Remote Similarity	NPD9261	Approved
0.6847	Remote Similarity	NPD9500	Approved
0.6846	Remote Similarity	NPD1607	Approved
0.6842	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6833	Remote Similarity	NPD1759	Phase 1
0.6829	Remote Similarity	NPD2337	Clinical (unspecified phase)
0.6825	Remote Similarity	NPD5736	Approved
0.6825	Remote Similarity	NPD4208	Discontinued
0.6822	Remote Similarity	NPD4060	Phase 1
0.6818	Remote Similarity	NPD5408	Approved
0.6818	Remote Similarity	NPD5405	Approved
0.6818	Remote Similarity	NPD5404	Approved
0.6818	Remote Similarity	NPD5406	Approved
0.6807	Remote Similarity	NPD7325	Clinical (unspecified phase)
0.6803	Remote Similarity	NPD3496	Discontinued
0.68	Remote Similarity	NPD3053	Approved
0.68	Remote Similarity	NPD4103	Phase 2
0.68	Remote Similarity	NPD4104	Clinical (unspecified phase)
0.68	Remote Similarity	NPD3094	Phase 2
0.68	Remote Similarity	NPD3055	Approved
0.6791	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6777	Remote Similarity	NPD1651	Approved
0.6772	Remote Similarity	NPD4908	Phase 1
0.6769	Remote Similarity	NPD4340	Discontinued
0.6767	Remote Similarity	NPD2344	Approved
0.6752	Remote Similarity	NPD821	Approved
0.675	Remote Similarity	NPD1758	Phase 1
0.675	Remote Similarity	NPD16	Approved
0.675	Remote Similarity	NPD856	Approved
0.6748	Remote Similarity	NPD1610	Phase 2
0.6746	Remote Similarity	NPD6584	Phase 3
0.6742	Remote Similarity	NPD3299	Clinical (unspecified phase)
0.6742	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.6741	Remote Similarity	NPD8166	Discontinued
0.6741	Remote Similarity	NPD3750	Approved
0.6729	Remote Similarity	NPD5122	Clinical (unspecified phase)
0.6723	Remote Similarity	NPD7157	Approved
0.6721	Remote Similarity	NPD6516	Phase 2
0.6721	Remote Similarity	NPD1751	Approved
0.6721	Remote Similarity	NPD2667	Approved
0.6721	Remote Similarity	NPD2668	Approved
0.6721	Remote Similarity	NPD5846	Approved
0.6719	Remote Similarity	NPD3027	Phase 3
0.6719	Remote Similarity	NPD7095	Approved
0.6716	Remote Similarity	NPD1549	Phase 2
0.6696	Remote Similarity	NPD6647	Phase 2
0.6696	Remote Similarity	NPD1931	Clinical (unspecified phase)
0.6696	Remote Similarity	NPD1930	Approved
0.6696	Remote Similarity	NPD1929	Approved
0.6694	Remote Similarity	NPD9269	Phase 2
0.6694	Remote Similarity	NPD2226	Clinical (unspecified phase)
0.6694	Remote Similarity	NPD7330	Discontinued
0.6694	Remote Similarity	NPD9717	Approved
0.6693	Remote Similarity	NPD9494	Approved
0.6693	Remote Similarity	NPD2861	Phase 2
0.6693	Remote Similarity	NPD4212	Discontinued
0.6691	Remote Similarity	NPD6190	Approved
0.6667	Remote Similarity	NPD2313	Discontinued
0.6667	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD9295	Approved
0.6667	Remote Similarity	NPD6798	Discontinued
0.6667	Remote Similarity	NPD1980	Approved
0.6667	Remote Similarity	NPD1981	Approved
0.6667	Remote Similarity	NPD1983	Approved
0.6667	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6642	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6642	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6641	Remote Similarity	NPD4207	Discontinued
0.6641	Remote Similarity	NPD2614	Approved
0.664	Remote Similarity	NPD1755	Approved
0.6639	Remote Similarity	NPD9268	Approved
0.6639	Remote Similarity	NPD475	Phase 2

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