NPASS Compound

Structure

CID201967 OpenBabel06191715592D 22 23 0 0 0 0 0 0 0 0999 V2000 6.9282 1.0000 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 6.9282 -0.0000 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 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 2.5981 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 3.4641 1.0000 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 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 4.3301 1.5000 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 4.3301 2.5000 0.0000 O 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 1 2 1 0 0 0 0 1 3 2 0 0 0 0 2 4 2 0 0 0 0 3 15 1 0 0 0 0 4 17 1 0 0 0 0 5 11 1 0 0 0 0 5 15 2 0 0 0 0 6 12 2 0 0 0 0 6 15 1 0 0 0 0 7 10 2 0 0 0 0 7 16 1 0 0 0 0 8 13 1 0 0 0 0 8 16 2 0 0 0 0 9 14 2 0 0 0 0 9 16 1 0 0 0 0 10 17 1 0 0 0 0 11 18 2 0 0 0 0 12 18 1 0 0 0 0 13 19 2 0 0 0 0 14 19 1 0 0 0 0 17 20 2 0 0 0 0 18 21 1 0 0 0 0 19 22 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	292.11
Volume:	320.073
LogP:	3.59
LogD:	3.631
LogS:	-3.549
# Rotatable Bonds:	5
TPSA:	57.53
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.648
Synthetic Accessibility Score:	2.41
Fsp3:	0.0
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.946
MDCK Permeability:	1.4178099263517652e-05
Pgp-inhibitor:	0.873
Pgp-substrate:	0.006
Human Intestinal Absorption (HIA):	0.015
20% Bioavailability (F20%):	0.001
30% Bioavailability (F30%):	0.008

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.229
Plasma Protein Binding (PPB):	100.3261947631836%
Volume Distribution (VD):	0.623
Pgp-substrate:	0.5194879174232483%

ADMET: Metabolism

CYP1A2-inhibitor:	0.802
CYP1A2-substrate:	0.074
CYP2C19-inhibitor:	0.468
CYP2C19-substrate:	0.063
CYP2C9-inhibitor:	0.487
CYP2C9-substrate:	0.913
CYP2D6-inhibitor:	0.064
CYP2D6-substrate:	0.921
CYP3A4-inhibitor:	0.479
CYP3A4-substrate:	0.312

ADMET: Excretion

Clearance (CL):	11.478
Half-life (T1/2):	0.934

ADMET: Toxicity

hERG Blockers:	0.438
Human Hepatotoxicity (H-HT):	0.405
Drug-inuced Liver Injury (DILI):	0.035
AMES Toxicity:	0.586
Rat Oral Acute Toxicity:	0.855
Maximum Recommended Daily Dose:	0.851
Skin Sensitization:	0.98
Carcinogencity:	0.405
Eye Corrosion:	0.007
Eye Irritation:	0.956
Respiratory Toxicity:	0.928

Download Data

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

Natural Product: NPC201967

Natural Product ID:	NPC201967
*Common Name:**	1,7-Bis(4-Hydroxyphenyl)-1,4,6-Heptatrien-3-One
IUPAC Name:	(1E,4E,6E)-1,7-bis(4-hydroxyphenyl)hepta-1,4,6-trien-3-one
Synonyms:
Standard InCHIKey:	PALMCMYYFAHUGA-BPTNNVFMSA-N
Standard InCHI:	InChI=1S/C19H16O3/c20-17(10-7-16-8-13-19(22)14-9-16)4-2-1-3-15-5-11-18(21)12-6-15/h1-14,21-22H/b3-1+,4-2+,10-7+
SMILES:	C(=Cc1ccc(cc1)O)/C=C/C(=O)/C=C/c1ccc(cc1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL469419
PubChem CID:	10447050
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0002650] Diarylheptanoids [CHEMONTID:0002651] Linear diarylheptanoids

*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
NPO30907	Curcuma domestica	Species	Zingiberaceae	Eukaryota	n.a.	rhizome	n.a.	DOI[10.1016/0031-9422(93)85548-6]
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]
NPO5878	Etlingera elatior	Species	Zingiberaceae	Eukaryota	n.a.	rhizome	n.a.	PMID[15730265]
NPO16667	Curcuma mangga	Species	Zingiberaceae	Eukaryota	rhizomes	n.a.	n.a.	PMID[16038556]
NPO7863	Dioscorea opposita	Species	Dioscoreaceae	Eukaryota	aerial parts	n.a.	n.a.	PMID[16124773]
NPO24124	Curcuma longa	Species	Zingiberaceae	Eukaryota	Rhizomes	n.a.	n.a.	PMID[23153397]
NPO24124	Curcuma longa	Species	Zingiberaceae	Eukaryota	n.a.	leaf	n.a.	PMID[23901173]
NPO5878	Etlingera elatior	Species	Zingiberaceae	Eukaryota	Flowers	Johor, Malaysia		PMID[26399961]
NPO5878	Etlingera elatior	Species	Zingiberaceae	Eukaryota	Flowers	Kelantan, Malaysia		PMID[26399961]
NPO5878	Etlingera elatior	Species	Zingiberaceae	Eukaryota	Flowers	Pahang, Malaysia		PMID[26399961]
NPO24124	Curcuma longa	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[28068085]
NPO24124	Curcuma longa	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9584408]
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]
NPO24124	Curcuma longa	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO24124	Curcuma longa	Species	Zingiberaceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO5878	Etlingera elatior	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]
NPO24124	Curcuma longa	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO7863	Dioscorea opposita	Species	Dioscoreaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO7863	Dioscorea opposita	Species	Dioscoreaceae	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]
NPO16667	Curcuma mangga	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5878	Etlingera elatior	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24124	Curcuma longa	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7863	Dioscorea opposita	Species	Dioscoreaceae	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
IC50	6
Others	4

Activity Type	# Activity
Cell Line	5
Individual Protein	2
NON-MOLECULAR	3
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT325	Individual Protein	Cyclooxygenase-2	Ovis aries	IC50	=	3.2	ug.mL-1	PMID[520005]
NPT324	Individual Protein	Cyclooxygenase-1	Ovis aries	IC50	=	5.8	ug.mL-1	PMID[520005]
NPT681	Cell Line	PC-12	Rattus norvegicus	ED50	>	50.0	ug ml-1	PMID[520006]
NPT91	Cell Line	KB	Homo sapiens	IC50	=	5750.0	nM	PMID[520009]
NPT189	Cell Line	Vero	Chlorocebus aethiops	IC50	=	9650.0	nM	PMID[520009]
NPT189	Cell Line	Vero	Chlorocebus aethiops	Ratio IC50	=	1.68	n.a.	PMID[520009]
NPT1	Others	Radical scavenging activity		IC50	>	100.0	ug.mL-1	PMID[520005]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	100.0	ug.mL-1	PMID[520005]
NPT2	Others	Unspecified		Ratio IC50	=	1.8	n.a.	PMID[520005]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	92.9	%	PMID[520007]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	92.09	%	PMID[520008]

☑ 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 NPC201967 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	233
0.1-0.2	2456
0.2-0.3	5762
0.3-0.4	12787
0.4-0.5	5463
0.5-0.6	9600
0.6-0.7	5249
0.7-0.8	979
0.8-0.85	105
0.85-0.9	50
0.9-0.95	9
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9891	High Similarity	NPC130193
0.9579	High Similarity	NPC68269
0.9375	High Similarity	NPC135784
0.9348	High Similarity	NPC181709
0.9286	High Similarity	NPC29989
0.9286	High Similarity	NPC95178
0.9286	High Similarity	NPC69332
0.9091	High Similarity	NPC70843
0.9043	High Similarity	NPC81010
0.9043	High Similarity	NPC151715
0.9043	High Similarity	NPC32977
0.901	High Similarity	NPC88141
0.9	High Similarity	NPC260952
0.8947	High Similarity	NPC286006
0.8947	High Similarity	NPC26244
0.8922	High Similarity	NPC116842
0.8889	High Similarity	NPC120693
0.8889	High Similarity	NPC8931
0.8889	High Similarity	NPC261573
0.8878	High Similarity	NPC472585
0.8854	High Similarity	NPC82664
0.8854	High Similarity	NPC473388
0.8854	High Similarity	NPC132271
0.8854	High Similarity	NPC216520
0.8854	High Similarity	NPC292730
0.8835	High Similarity	NPC297657
0.883	High Similarity	NPC45040
0.875	High Similarity	NPC51698
0.8738	High Similarity	NPC183700
0.8725	High Similarity	NPC206341
0.8725	High Similarity	NPC17525
0.8713	High Similarity	NPC188677
0.8681	High Similarity	NPC265146
0.8673	High Similarity	NPC132078
0.8673	High Similarity	NPC78119
0.8673	High Similarity	NPC216468
0.8673	High Similarity	NPC51333
0.8646	High Similarity	NPC128062
0.8632	High Similarity	NPC270547
0.8617	High Similarity	NPC177420
0.8617	High Similarity	NPC280347
0.8617	High Similarity	NPC98772
0.8602	High Similarity	NPC184169
0.8587	High Similarity	NPC175313
0.8587	High Similarity	NPC248817
0.8586	High Similarity	NPC253746
0.8586	High Similarity	NPC213730
0.8585	High Similarity	NPC285350
0.8571	High Similarity	NPC228988
0.8558	High Similarity	NPC222905
0.8558	High Similarity	NPC21162
0.8557	High Similarity	NPC246679
0.8557	High Similarity	NPC274678
0.8557	High Similarity	NPC257182
0.8526	High Similarity	NPC55561
0.8515	High Similarity	NPC79672
0.8511	High Similarity	NPC25493
0.8511	High Similarity	NPC104216
0.8511	High Similarity	NPC113460
0.8505	High Similarity	NPC23402
0.8505	High Similarity	NPC322197
0.85	High Similarity	NPC91461
0.85	High Similarity	NPC7686
0.85	High Similarity	NPC40258
0.8495	Intermediate Similarity	NPC197783
0.8485	Intermediate Similarity	NPC92730
0.8478	Intermediate Similarity	NPC124436
0.8476	Intermediate Similarity	NPC268388
0.8476	Intermediate Similarity	NPC470355
0.8469	Intermediate Similarity	NPC283711
0.8462	Intermediate Similarity	NPC79543
0.8454	Intermediate Similarity	NPC76938
0.8447	Intermediate Similarity	NPC141523
0.8431	Intermediate Similarity	NPC243677
0.8431	Intermediate Similarity	NPC303141
0.8426	Intermediate Similarity	NPC277394
0.8426	Intermediate Similarity	NPC299252
0.8426	Intermediate Similarity	NPC61062
0.8426	Intermediate Similarity	NPC19290
0.8421	Intermediate Similarity	NPC123273
0.8421	Intermediate Similarity	NPC242240
0.8421	Intermediate Similarity	NPC318325
0.8416	Intermediate Similarity	NPC168829
0.8416	Intermediate Similarity	NPC304638
0.8416	Intermediate Similarity	NPC470202
0.8404	Intermediate Similarity	NPC23167
0.8384	Intermediate Similarity	NPC140619
0.8384	Intermediate Similarity	NPC225464
0.8384	Intermediate Similarity	NPC260000
0.8381	Intermediate Similarity	NPC321252
0.8381	Intermediate Similarity	NPC252544
0.8367	Intermediate Similarity	NPC32714
0.835	Intermediate Similarity	NPC6984
0.8333	Intermediate Similarity	NPC300017
0.8333	Intermediate Similarity	NPC52087
0.8333	Intermediate Similarity	NPC288411
0.8302	Intermediate Similarity	NPC177576
0.83	Intermediate Similarity	NPC275104
0.83	Intermediate Similarity	NPC280869
0.8286	Intermediate Similarity	NPC95172
0.8273	Intermediate Similarity	NPC249435
0.8269	Intermediate Similarity	NPC226699
0.8252	Intermediate Similarity	NPC127676
0.8252	Intermediate Similarity	NPC233396
0.8252	Intermediate Similarity	NPC138942
0.8252	Intermediate Similarity	NPC474839
0.8252	Intermediate Similarity	NPC154899
0.8229	Intermediate Similarity	NPC258219
0.8224	Intermediate Similarity	NPC286222
0.8218	Intermediate Similarity	NPC275053
0.8218	Intermediate Similarity	NPC248573
0.8218	Intermediate Similarity	NPC223393
0.8218	Intermediate Similarity	NPC294741
0.8218	Intermediate Similarity	NPC161571
0.8208	Intermediate Similarity	NPC63345
0.82	Intermediate Similarity	NPC32674
0.819	Intermediate Similarity	NPC470039
0.8173	Intermediate Similarity	NPC113457
0.8173	Intermediate Similarity	NPC92623
0.8173	Intermediate Similarity	NPC19149
0.8173	Intermediate Similarity	NPC294902
0.8173	Intermediate Similarity	NPC1075
0.8173	Intermediate Similarity	NPC135464
0.8173	Intermediate Similarity	NPC1786
0.8163	Intermediate Similarity	NPC271440
0.8163	Intermediate Similarity	NPC138117
0.8163	Intermediate Similarity	NPC325292
0.8155	Intermediate Similarity	NPC119860
0.8144	Intermediate Similarity	NPC192
0.8144	Intermediate Similarity	NPC300478
0.8137	Intermediate Similarity	NPC94343
0.8131	Intermediate Similarity	NPC139946
0.8119	Intermediate Similarity	NPC245561
0.8119	Intermediate Similarity	NPC171843
0.8113	Intermediate Similarity	NPC75272
0.8113	Intermediate Similarity	NPC471954
0.8105	Intermediate Similarity	NPC155393
0.8081	Intermediate Similarity	NPC316301
0.8081	Intermediate Similarity	NPC27323
0.8061	Intermediate Similarity	NPC155908
0.8061	Intermediate Similarity	NPC304541
0.8061	Intermediate Similarity	NPC204210
0.8053	Intermediate Similarity	NPC224814
0.8053	Intermediate Similarity	NPC14007
0.8053	Intermediate Similarity	NPC60962
0.8053	Intermediate Similarity	NPC189844
0.8053	Intermediate Similarity	NPC109083
0.8053	Intermediate Similarity	NPC269843
0.8053	Intermediate Similarity	NPC71870
0.8039	Intermediate Similarity	NPC52472
0.8036	Intermediate Similarity	NPC263386
0.8036	Intermediate Similarity	NPC141791
0.8021	Intermediate Similarity	NPC307235
0.8021	Intermediate Similarity	NPC407
0.802	Intermediate Similarity	NPC175298
0.802	Intermediate Similarity	NPC291789
0.8019	Intermediate Similarity	NPC24101
0.8019	Intermediate Similarity	NPC11554
0.8019	Intermediate Similarity	NPC317305
0.8019	Intermediate Similarity	NPC61885
0.8019	Intermediate Similarity	NPC262365
0.8019	Intermediate Similarity	NPC63698
0.8019	Intermediate Similarity	NPC96224
0.8019	Intermediate Similarity	NPC201959
0.8018	Intermediate Similarity	NPC280001
0.8018	Intermediate Similarity	NPC278652
0.8	Intermediate Similarity	NPC286904
0.8	Intermediate Similarity	NPC313650
0.8	Intermediate Similarity	NPC271274
0.8	Intermediate Similarity	NPC296526
0.8	Intermediate Similarity	NPC150837
0.7982	Intermediate Similarity	NPC242136
0.7981	Intermediate Similarity	NPC2518
0.7981	Intermediate Similarity	NPC471511
0.7981	Intermediate Similarity	NPC323810
0.7981	Intermediate Similarity	NPC474603
0.7981	Intermediate Similarity	NPC241891
0.7981	Intermediate Similarity	NPC12987
0.7981	Intermediate Similarity	NPC30506
0.7981	Intermediate Similarity	NPC93831
0.798	Intermediate Similarity	NPC306884
0.798	Intermediate Similarity	NPC162314
0.798	Intermediate Similarity	NPC94139
0.798	Intermediate Similarity	NPC147284
0.798	Intermediate Similarity	NPC210497
0.798	Intermediate Similarity	NPC3358
0.7963	Intermediate Similarity	NPC212718
0.7963	Intermediate Similarity	NPC114682
0.7961	Intermediate Similarity	NPC471578
0.7961	Intermediate Similarity	NPC101025
0.7946	Intermediate Similarity	NPC275519
0.7944	Intermediate Similarity	NPC254833
0.7944	Intermediate Similarity	NPC55617
0.7944	Intermediate Similarity	NPC62258
0.7944	Intermediate Similarity	NPC265211
0.7944	Intermediate Similarity	NPC228343
0.7944	Intermediate Similarity	NPC98392
0.7944	Intermediate Similarity	NPC306045
0.7941	Intermediate Similarity	NPC128723
0.7938	Intermediate Similarity	NPC27974

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 NPC201967 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	225
0.1-0.2	1137
0.2-0.3	1073
0.3-0.4	2960
0.4-0.5	2148
0.5-0.6	1150
0.6-0.7	397
0.7-0.8	52
0.8-0.85	3
0.85-0.9	5
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9043	High Similarity	NPD2934	Approved
0.9043	High Similarity	NPD2933	Approved
0.8947	High Similarity	NPD2859	Approved
0.8947	High Similarity	NPD2860	Approved
0.8673	High Similarity	NPD3020	Approved
0.8478	Intermediate Similarity	NPD111	Approved
0.8218	Intermediate Similarity	NPD1242	Phase 1
0.8081	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.7944	Intermediate Similarity	NPD3021	Approved
0.7944	Intermediate Similarity	NPD3022	Approved
0.7864	Intermediate Similarity	NPD3028	Approved
0.7845	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7788	Intermediate Similarity	NPD940	Approved
0.7788	Intermediate Similarity	NPD846	Approved
0.7757	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7664	Intermediate Similarity	NPD3134	Approved
0.7647	Intermediate Similarity	NPD844	Approved
0.7647	Intermediate Similarity	NPD1809	Phase 2
0.7624	Intermediate Similarity	NPD845	Approved
0.7544	Intermediate Similarity	NPD5536	Phase 2
0.75	Intermediate Similarity	NPD3019	Approved
0.75	Intermediate Similarity	NPD968	Approved
0.75	Intermediate Similarity	NPD2229	Approved
0.75	Intermediate Similarity	NPD2234	Approved
0.75	Intermediate Similarity	NPD2932	Approved
0.75	Intermediate Similarity	NPD2228	Approved
0.7473	Intermediate Similarity	NPD9087	Approved
0.7431	Intermediate Similarity	NPD1358	Approved
0.7414	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7404	Intermediate Similarity	NPD288	Approved
0.7364	Intermediate Similarity	NPD9266	Approved
0.7364	Intermediate Similarity	NPD74	Approved
0.7358	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.734	Intermediate Similarity	NPD9088	Approved
0.7328	Intermediate Similarity	NPD9545	Approved
0.7315	Intermediate Similarity	NPD9608	Approved
0.7315	Intermediate Similarity	NPD1237	Approved
0.7315	Intermediate Similarity	NPD9610	Approved
0.7304	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD9267	Approved
0.7273	Intermediate Similarity	NPD9264	Approved
0.7273	Intermediate Similarity	NPD1164	Approved
0.7273	Intermediate Similarity	NPD9263	Approved
0.7273	Intermediate Similarity	NPD2342	Discontinued
0.7257	Intermediate Similarity	NPD7635	Approved
0.7257	Intermediate Similarity	NPD5535	Approved
0.7227	Intermediate Similarity	NPD1201	Approved
0.7203	Intermediate Similarity	NPD5238	Clinical (unspecified phase)
0.7193	Intermediate Similarity	NPD1241	Discontinued
0.7179	Intermediate Similarity	NPD5303	Approved
0.7179	Intermediate Similarity	NPD3091	Approved
0.7179	Intermediate Similarity	NPD5304	Approved
0.717	Intermediate Similarity	NPD9273	Approved
0.7167	Intermediate Similarity	NPD3972	Approved
0.7155	Intermediate Similarity	NPD9493	Approved
0.7143	Intermediate Similarity	NPD3421	Phase 3
0.7143	Intermediate Similarity	NPD4750	Phase 3
0.7143	Intermediate Similarity	NPD1792	Phase 2
0.7143	Intermediate Similarity	NPD9380	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD3847	Discontinued
0.7143	Intermediate Similarity	NPD5451	Approved
0.7131	Intermediate Similarity	NPD1470	Approved
0.712	Intermediate Similarity	NPD3764	Approved
0.7119	Intermediate Similarity	NPD4093	Discontinued
0.7091	Intermediate Similarity	NPD9697	Approved
0.7083	Intermediate Similarity	NPD1535	Discovery
0.7083	Intermediate Similarity	NPD422	Phase 1
0.7069	Intermediate Similarity	NPD255	Approved
0.7069	Intermediate Similarity	NPD256	Approved
0.7059	Intermediate Similarity	NPD4626	Approved
0.7059	Intermediate Similarity	NPD4589	Approved
0.7059	Intermediate Similarity	NPD2286	Discontinued
0.7059	Intermediate Similarity	NPD4059	Approved
0.7054	Intermediate Similarity	NPD2684	Approved
0.7053	Intermediate Similarity	NPD9294	Approved
0.7041	Intermediate Similarity	NPD9089	Approved
0.7034	Intermediate Similarity	NPD1548	Phase 1
0.7034	Intermediate Similarity	NPD1894	Discontinued
0.7027	Intermediate Similarity	NPD1445	Approved
0.7027	Intermediate Similarity	NPD1444	Approved
0.7025	Intermediate Similarity	NPD2562	Approved
0.7025	Intermediate Similarity	NPD1481	Phase 2
0.7025	Intermediate Similarity	NPD2561	Approved
0.7021	Intermediate Similarity	NPD9716	Approved
0.7018	Intermediate Similarity	NPD6124	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD228	Approved
0.7009	Intermediate Similarity	NPD9568	Approved
0.7008	Intermediate Similarity	NPD943	Approved
0.7008	Intermediate Similarity	NPD1240	Approved
0.6992	Remote Similarity	NPD1203	Approved
0.6992	Remote Similarity	NPD2797	Approved
0.699	Remote Similarity	NPD9258	Approved
0.699	Remote Similarity	NPD9256	Approved
0.6983	Remote Similarity	NPD1476	Clinical (unspecified phase)
0.697	Remote Similarity	NPD3971	Phase 1
0.6967	Remote Similarity	NPD6583	Phase 3
0.6967	Remote Similarity	NPD6582	Phase 2
0.6967	Remote Similarity	NPD4659	Approved
0.6967	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD9377	Approved
0.6957	Remote Similarity	NPD9379	Approved
0.6952	Remote Similarity	NPD1202	Approved
0.6944	Remote Similarity	NPD2066	Phase 3
0.6942	Remote Similarity	NPD3092	Approved
0.6939	Remote Similarity	NPD9093	Approved
0.6935	Remote Similarity	NPD2798	Approved
0.6923	Remote Similarity	NPD6671	Approved
0.6911	Remote Similarity	NPD5311	Approved
0.6911	Remote Similarity	NPD5310	Approved
0.6911	Remote Similarity	NPD3225	Approved
0.6911	Remote Similarity	NPD1876	Approved
0.6909	Remote Similarity	NPD9261	Approved
0.6909	Remote Similarity	NPD9500	Approved
0.6899	Remote Similarity	NPD1607	Approved
0.6897	Remote Similarity	NPD5283	Phase 1
0.6897	Remote Similarity	NPD7159	Clinical (unspecified phase)
0.6885	Remote Similarity	NPD2337	Clinical (unspecified phase)
0.688	Remote Similarity	NPD4208	Discontinued
0.688	Remote Similarity	NPD5736	Approved
0.687	Remote Similarity	NPD2935	Discontinued
0.686	Remote Similarity	NPD3026	Approved
0.686	Remote Similarity	NPD3023	Approved
0.6855	Remote Similarity	NPD4339	Clinical (unspecified phase)
0.6855	Remote Similarity	NPD3055	Approved
0.6855	Remote Similarity	NPD4104	Clinical (unspecified phase)
0.6855	Remote Similarity	NPD4103	Phase 2
0.6855	Remote Similarity	NPD3053	Approved
0.685	Remote Similarity	NPD3268	Approved
0.6838	Remote Similarity	NPD9281	Approved
0.6833	Remote Similarity	NPD1651	Approved
0.6833	Remote Similarity	NPD3024	Approved
0.6833	Remote Similarity	NPD3025	Approved
0.6818	Remote Similarity	NPD7266	Discontinued
0.6818	Remote Similarity	NPD2344	Approved
0.681	Remote Similarity	NPD821	Approved
0.681	Remote Similarity	NPD7843	Approved
0.6807	Remote Similarity	NPD16	Approved
0.6807	Remote Similarity	NPD856	Approved
0.6803	Remote Similarity	NPD1610	Phase 2
0.68	Remote Similarity	NPD6584	Phase 3
0.68	Remote Similarity	NPD7451	Discontinued
0.6794	Remote Similarity	NPD2799	Discontinued
0.6794	Remote Similarity	NPD1510	Phase 2
0.6783	Remote Similarity	NPD9280	Clinical (unspecified phase)
0.6777	Remote Similarity	NPD2667	Approved
0.6777	Remote Similarity	NPD5846	Approved
0.6777	Remote Similarity	NPD1751	Approved
0.6777	Remote Similarity	NPD6516	Phase 2
0.6777	Remote Similarity	NPD2668	Approved
0.6777	Remote Similarity	NPD3095	Discontinued
0.6757	Remote Similarity	NPD1930	Approved
0.6757	Remote Similarity	NPD1929	Approved
0.6757	Remote Similarity	NPD1931	Clinical (unspecified phase)
0.6754	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.675	Remote Similarity	NPD2226	Clinical (unspecified phase)
0.675	Remote Similarity	NPD7330	Discontinued
0.675	Remote Similarity	NPD1759	Phase 1
0.6746	Remote Similarity	NPD2861	Phase 2
0.6746	Remote Similarity	NPD4212	Discontinued
0.6746	Remote Similarity	NPD9494	Approved
0.6744	Remote Similarity	NPD4060	Phase 1
0.6742	Remote Similarity	NPD5405	Approved
0.6742	Remote Similarity	NPD5408	Approved
0.6742	Remote Similarity	NPD5406	Approved
0.6742	Remote Similarity	NPD5404	Approved
0.6731	Remote Similarity	NPD9295	Approved
0.6723	Remote Similarity	NPD7325	Clinical (unspecified phase)
0.6721	Remote Similarity	NPD1980	Approved
0.6721	Remote Similarity	NPD1981	Approved
0.6721	Remote Similarity	NPD1983	Approved
0.6721	Remote Similarity	NPD3496	Discontinued
0.672	Remote Similarity	NPD3094	Phase 2
0.6716	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6696	Remote Similarity	NPD5909	Discontinued
0.6695	Remote Similarity	NPD5951	Approved
0.6694	Remote Similarity	NPD1755	Approved
0.6694	Remote Similarity	NPD5691	Approved
0.6693	Remote Similarity	NPD4908	Phase 1
0.6693	Remote Similarity	NPD4207	Discontinued
0.6692	Remote Similarity	NPD4340	Discontinued
0.6667	Remote Similarity	NPD3750	Approved
0.6667	Remote Similarity	NPD6663	Approved
0.6667	Remote Similarity	NPD3299	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD290	Approved
0.6667	Remote Similarity	NPD318	Approved
0.6667	Remote Similarity	NPD5350	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5351	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD317	Approved
0.6667	Remote Similarity	NPD8166	Discontinued
0.6667	Remote Similarity	NPD9073	Approved
0.6667	Remote Similarity	NPD1758	Phase 1
0.6642	Remote Similarity	NPD1549	Phase 2
0.6641	Remote Similarity	NPD3027	Phase 3
0.6641	Remote Similarity	NPD7095	Approved
0.6641	Remote Similarity	NPD5163	Phase 2
0.664	Remote Similarity	NPD1283	Approved
0.6639	Remote Similarity	NPD7157	Approved
0.6639	Remote Similarity	NPD2423	Clinical (unspecified phase)

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