NPASS Compound

Structure

CID70843 OpenBabel06191715412D 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 1 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:	342.11
Volume:	343.16
LogP:	3.532
LogD:	2.991
LogS:	-5.211
# Rotatable Bonds:	5
TPSA:	67.13
# H-Bond Aceptor:	6
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.707
Synthetic Accessibility Score:	2.11
Fsp3:	0.211
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:	-4.665
MDCK Permeability:	6.163905345601961e-05
Pgp-inhibitor:	0.999
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.008
20% Bioavailability (F20%):	0.008
30% Bioavailability (F30%):	0.168

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.137
Plasma Protein Binding (PPB):	75.19342803955078%
Volume Distribution (VD):	0.872
Pgp-substrate:	16.654787063598633%

ADMET: Metabolism

CYP1A2-inhibitor:	0.849
CYP1A2-substrate:	0.976
CYP2C19-inhibitor:	0.773
CYP2C19-substrate:	0.827
CYP2C9-inhibitor:	0.702
CYP2C9-substrate:	0.924
CYP2D6-inhibitor:	0.15
CYP2D6-substrate:	0.953
CYP3A4-inhibitor:	0.839
CYP3A4-substrate:	0.483

ADMET: Excretion

Clearance (CL):	6.931
Half-life (T1/2):	0.463

ADMET: Toxicity

hERG Blockers:	0.108
Human Hepatotoxicity (H-HT):	0.13
Drug-inuced Liver Injury (DILI):	0.914
AMES Toxicity:	0.421
Rat Oral Acute Toxicity:	0.086
Maximum Recommended Daily Dose:	0.215
Skin Sensitization:	0.43
Carcinogencity:	0.037
Eye Corrosion:	0.004
Eye Irritation:	0.198
Respiratory Toxicity:	0.523

Download Data

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

Natural Product: NPC70843

Natural Product ID:	NPC70843
*Common Name:**	1,2-Dihydrobis(De-O-Methyl)-Curcumin
IUPAC Name:	(4Z,6E)-5-hydroxy-1,7-bis(4-hydroxyphenyl)hepta-4,6-dien-3-one
Synonyms:
Standard InCHIKey:	XLKHKZCPVAHTFN-YLMKKNOUSA-N
Standard InCHI:	InChI=1S/C19H18O4/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/h1-5,7-11,13,20-22H,6,12H2/b11-5+,18-13-
SMILES:	c1cc(ccc1/C=C/C(=C/C(=O)CCc1ccc(cc1)O)/O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL448759
PubChem CID:	10614892
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
NPO6836	Alpinia blepharocalyx	Species	Zingiberaceae	Eukaryota	seeds	Mengha, Yunnan Province, China	1991-Aug	PMID[11277741]
NPO6836	Alpinia blepharocalyx	Species	Zingiberaceae	Eukaryota	seeds	n.a.	n.a.	PMID[11325233]
NPO6836	Alpinia blepharocalyx	Species	Zingiberaceae	Eukaryota	Seeds	n.a.	n.a.	PMID[11430002]
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]
NPO33355	aframomum letestuianum	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12662093]
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]
NPO24124	Curcuma longa	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[28068085]
NPO6836	Alpinia blepharocalyx	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9461664]
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]
NPO6836	Alpinia blepharocalyx	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO24124	Curcuma longa	Species	Zingiberaceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO24124	Curcuma longa	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6836	Alpinia blepharocalyx	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]
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]
NPO6836	Alpinia blepharocalyx	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
ED50	2
IC50	3
Others	4

Activity Type	# Activity
Cell Line	1
NON-MOLECULAR	5
Organism	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT453	Cell Line	HT-1080	Homo sapiens	ED50	>	100.0	uM	PMID[569860]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	ED50	=	62.6	uM	PMID[569860]
NPT471	Organism	Trypanosoma brucei brucei	Trypanosoma brucei brucei	IC50	=	2.6	ug.mL-1	PMID[569861]
NPT844	Organism	Trypanosoma brucei rhodesiense	Trypanosoma brucei rhodesiense	IC50	=	2.8	ug.mL-1	PMID[569861]
NPT844	Organism	Trypanosoma brucei rhodesiense	Trypanosoma brucei rhodesiense	IC50	=	1.3	ug.mL-1	PMID[569861]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	77.3	%	PMID[569862]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	100.0	%	PMID[569862]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	62.8	%	PMID[569862]

☑ 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 NPC70843 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	242
0.1-0.2	1476
0.2-0.3	4191
0.3-0.4	11784
0.4-0.5	7211
0.5-0.6	7774
0.6-0.7	7969
0.7-0.8	1828
0.8-0.85	160
0.85-0.9	36
0.9-0.95	17
0.95-1	9

Similarity Score	Similarity Level	Natural Product ID
0.9798	High Similarity	NPC29989
0.9798	High Similarity	NPC95178
0.9798	High Similarity	NPC69332
0.9703	High Similarity	NPC88141
0.96	High Similarity	NPC188677
0.9596	High Similarity	NPC261573
0.9596	High Similarity	NPC120693
0.9596	High Similarity	NPC8931
0.9417	High Similarity	NPC21162
0.93	High Similarity	NPC68269
0.9245	High Similarity	NPC285350
0.9231	High Similarity	NPC116842
0.9192	High Similarity	NPC130193
0.9159	High Similarity	NPC23402
0.9143	High Similarity	NPC177576
0.9091	High Similarity	NPC260000
0.9091	High Similarity	NPC201967
0.9074	High Similarity	NPC277394
0.9074	High Similarity	NPC299252
0.9074	High Similarity	NPC61062
0.9048	High Similarity	NPC252544
0.9048	High Similarity	NPC321252
0.9038	High Similarity	NPC17525
0.9	High Similarity	NPC280869
0.8981	High Similarity	NPC322197
0.8942	High Similarity	NPC141523
0.8922	High Similarity	NPC135784
0.8899	High Similarity	NPC19290
0.8879	High Similarity	NPC286222
0.8868	High Similarity	NPC222905
0.8812	High Similarity	NPC245561
0.8788	High Similarity	NPC151715
0.8785	High Similarity	NPC268388
0.8774	High Similarity	NPC95172
0.8762	High Similarity	NPC226699
0.875	High Similarity	NPC13495
0.8739	High Similarity	NPC249435
0.8727	High Similarity	NPC128249
0.8725	High Similarity	NPC52472
0.87	High Similarity	NPC26244
0.8679	High Similarity	NPC317305
0.8667	High Similarity	NPC6984
0.8641	High Similarity	NPC472585
0.8614	High Similarity	NPC473388
0.8611	High Similarity	NPC297657
0.8596	High Similarity	NPC196976
0.8586	High Similarity	NPC45040
0.8585	High Similarity	NPC228737
0.8571	High Similarity	NPC471033
0.8571	High Similarity	NPC311091
0.8559	High Similarity	NPC325646
0.8559	High Similarity	NPC28951
0.8532	High Similarity	NPC51698
0.8522	High Similarity	NPC86900
0.8519	High Similarity	NPC183700
0.8509	High Similarity	NPC236520
0.8509	High Similarity	NPC294361
0.8505	High Similarity	NPC31274
0.85	High Similarity	NPC181709
0.8496	Intermediate Similarity	NPC158222
0.8496	Intermediate Similarity	NPC182240
0.8462	Intermediate Similarity	NPC91461
0.8462	Intermediate Similarity	NPC7686
0.8462	Intermediate Similarity	NPC40258
0.8455	Intermediate Similarity	NPC242136
0.8447	Intermediate Similarity	NPC216468
0.8447	Intermediate Similarity	NPC78119
0.8447	Intermediate Similarity	NPC132078
0.8447	Intermediate Similarity	NPC51333
0.844	Intermediate Similarity	NPC212718
0.844	Intermediate Similarity	NPC114682
0.8431	Intermediate Similarity	NPC216520
0.8431	Intermediate Similarity	NPC82664
0.8431	Intermediate Similarity	NPC292730
0.8431	Intermediate Similarity	NPC132271
0.8426	Intermediate Similarity	NPC79543
0.8421	Intermediate Similarity	NPC34634
0.8421	Intermediate Similarity	NPC265454
0.8421	Intermediate Similarity	NPC159525
0.8421	Intermediate Similarity	NPC473136
0.8416	Intermediate Similarity	NPC128062
0.8411	Intermediate Similarity	NPC34715
0.8384	Intermediate Similarity	NPC280347
0.8384	Intermediate Similarity	NPC177420
0.8365	Intermediate Similarity	NPC213730
0.8364	Intermediate Similarity	NPC17693
0.8362	Intermediate Similarity	NPC68167
0.8348	Intermediate Similarity	NPC248363
0.8348	Intermediate Similarity	NPC98305
0.8333	Intermediate Similarity	NPC188814
0.8333	Intermediate Similarity	NPC264976
0.8333	Intermediate Similarity	NPC224584
0.8333	Intermediate Similarity	NPC195262
0.8333	Intermediate Similarity	NPC274678
0.8304	Intermediate Similarity	NPC51345
0.83	Intermediate Similarity	NPC55561
0.8291	Intermediate Similarity	NPC14141
0.8288	Intermediate Similarity	NPC11824
0.8283	Intermediate Similarity	NPC113460
0.8283	Intermediate Similarity	NPC25493
0.8276	Intermediate Similarity	NPC73532
0.8276	Intermediate Similarity	NPC19174
0.8276	Intermediate Similarity	NPC45438
0.8276	Intermediate Similarity	NPC267552
0.8276	Intermediate Similarity	NPC143427
0.8276	Intermediate Similarity	NPC242895
0.8276	Intermediate Similarity	NPC224273
0.8276	Intermediate Similarity	NPC115159
0.8276	Intermediate Similarity	NPC31936
0.8273	Intermediate Similarity	NPC470355
0.8269	Intermediate Similarity	NPC92730
0.8257	Intermediate Similarity	NPC326187
0.8252	Intermediate Similarity	NPC289201
0.8246	Intermediate Similarity	NPC184527
0.8241	Intermediate Similarity	NPC260952
0.8235	Intermediate Similarity	NPC303680
0.8235	Intermediate Similarity	NPC84076
0.8235	Intermediate Similarity	NPC76938
0.8235	Intermediate Similarity	NPC267846
0.8235	Intermediate Similarity	NPC81010
0.8235	Intermediate Similarity	NPC90128
0.8235	Intermediate Similarity	NPC32977
0.8208	Intermediate Similarity	NPC13426
0.8208	Intermediate Similarity	NPC168829
0.8205	Intermediate Similarity	NPC32032
0.8205	Intermediate Similarity	NPC139171
0.8205	Intermediate Similarity	NPC91478
0.8205	Intermediate Similarity	NPC133909
0.82	Intermediate Similarity	NPC123273
0.82	Intermediate Similarity	NPC242240
0.82	Intermediate Similarity	NPC318325
0.8198	Intermediate Similarity	NPC228988
0.8198	Intermediate Similarity	NPC231717
0.819	Intermediate Similarity	NPC297186
0.819	Intermediate Similarity	NPC216216
0.8182	Intermediate Similarity	NPC63345
0.8182	Intermediate Similarity	NPC222084
0.8182	Intermediate Similarity	NPC23167
0.8174	Intermediate Similarity	NPC473974
0.8174	Intermediate Similarity	NPC79933
0.8174	Intermediate Similarity	NPC258366
0.8174	Intermediate Similarity	NPC31296
0.8173	Intermediate Similarity	NPC225464
0.8167	Intermediate Similarity	NPC72158
0.8167	Intermediate Similarity	NPC23126
0.8167	Intermediate Similarity	NPC266689
0.8167	Intermediate Similarity	NPC30501
0.8167	Intermediate Similarity	NPC5018
0.8167	Intermediate Similarity	NPC162612
0.8167	Intermediate Similarity	NPC116513
0.8167	Intermediate Similarity	NPC98254
0.8167	Intermediate Similarity	NPC169250
0.8167	Intermediate Similarity	NPC276466
0.8167	Intermediate Similarity	NPC123722
0.8167	Intermediate Similarity	NPC103356
0.8167	Intermediate Similarity	NPC100067
0.8167	Intermediate Similarity	NPC105157
0.8167	Intermediate Similarity	NPC190043
0.8167	Intermediate Similarity	NPC151167
0.8167	Intermediate Similarity	NPC123228
0.8165	Intermediate Similarity	NPC206341
0.8163	Intermediate Similarity	NPC175313
0.8158	Intermediate Similarity	NPC76308
0.8158	Intermediate Similarity	NPC325295
0.8155	Intermediate Similarity	NPC32714
0.8155	Intermediate Similarity	NPC286006
0.8131	Intermediate Similarity	NPC288411
0.812	Intermediate Similarity	NPC472271
0.812	Intermediate Similarity	NPC295034
0.812	Intermediate Similarity	NPC156139
0.812	Intermediate Similarity	NPC154696
0.812	Intermediate Similarity	NPC198336
0.812	Intermediate Similarity	NPC120545
0.8119	Intermediate Similarity	NPC300017
0.8108	Intermediate Similarity	NPC228609
0.8103	Intermediate Similarity	NPC190501
0.8103	Intermediate Similarity	NPC318552
0.8099	Intermediate Similarity	NPC21305
0.8099	Intermediate Similarity	NPC221777
0.8099	Intermediate Similarity	NPC473017
0.8087	Intermediate Similarity	NPC474890
0.8087	Intermediate Similarity	NPC161943
0.8087	Intermediate Similarity	NPC273282
0.8083	Intermediate Similarity	NPC62952
0.8083	Intermediate Similarity	NPC179777
0.8081	Intermediate Similarity	NPC197783
0.8073	Intermediate Similarity	NPC29883
0.807	Intermediate Similarity	NPC471924
0.807	Intermediate Similarity	NPC477453
0.807	Intermediate Similarity	NPC471925
0.807	Intermediate Similarity	NPC471928
0.8067	Intermediate Similarity	NPC474766
0.8067	Intermediate Similarity	NPC13238
0.8067	Intermediate Similarity	NPC474803
0.8067	Intermediate Similarity	NPC164014
0.8067	Intermediate Similarity	NPC288945
0.8067	Intermediate Similarity	NPC231767
0.8061	Intermediate Similarity	NPC265146
0.8061	Intermediate Similarity	NPC123476
0.8056	Intermediate Similarity	NPC303141

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 NPC70843 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	239
0.1-0.2	960
0.2-0.3	1101
0.3-0.4	2639
0.4-0.5	2266
0.5-0.6	1340
0.6-0.7	499
0.7-0.8	98
0.8-0.85	4
0.85-0.9	4
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8788	High Similarity	NPD2933	Approved
0.8788	High Similarity	NPD2934	Approved
0.87	High Similarity	NPD2860	Approved
0.87	High Similarity	NPD2859	Approved
0.8447	Intermediate Similarity	NPD3020	Approved
0.8103	Intermediate Similarity	NPD3019	Approved
0.8103	Intermediate Similarity	NPD2932	Approved
0.8073	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7928	Intermediate Similarity	NPD3022	Approved
0.7928	Intermediate Similarity	NPD3021	Approved
0.7885	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.7879	Intermediate Similarity	NPD111	Approved
0.7863	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.785	Intermediate Similarity	NPD3028	Approved
0.7815	Intermediate Similarity	NPD1201	Approved
0.7815	Intermediate Similarity	NPD1535	Discovery
0.7798	Intermediate Similarity	NPD1237	Approved
0.7759	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.775	Intermediate Similarity	NPD1481	Phase 2
0.7705	Intermediate Similarity	NPD1164	Approved
0.7705	Intermediate Similarity	NPD1470	Approved
0.7686	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7685	Intermediate Similarity	NPD1242	Phase 1
0.768	Intermediate Similarity	NPD3764	Approved
0.7679	Intermediate Similarity	NPD74	Approved
0.7679	Intermediate Similarity	NPD9266	Approved
0.7672	Intermediate Similarity	NPD256	Approved
0.7672	Intermediate Similarity	NPD255	Approved
0.7652	Intermediate Similarity	NPD1241	Discontinued
0.7627	Intermediate Similarity	NPD1894	Discontinued
0.7627	Intermediate Similarity	NPD9545	Approved
0.7615	Intermediate Similarity	NPD846	Approved
0.7615	Intermediate Similarity	NPD940	Approved
0.7607	Intermediate Similarity	NPD9568	Approved
0.7603	Intermediate Similarity	NPD3972	Approved
0.7589	Intermediate Similarity	NPD9264	Approved
0.7589	Intermediate Similarity	NPD9267	Approved
0.7589	Intermediate Similarity	NPD9263	Approved
0.7583	Intermediate Similarity	NPD3026	Approved
0.7583	Intermediate Similarity	NPD3023	Approved
0.7583	Intermediate Similarity	NPD3847	Discontinued
0.7563	Intermediate Similarity	NPD3024	Approved
0.7563	Intermediate Similarity	NPD3025	Approved
0.7561	Intermediate Similarity	NPD2797	Approved
0.7559	Intermediate Similarity	NPD943	Approved
0.754	Intermediate Similarity	NPD3268	Approved
0.7479	Intermediate Similarity	NPD1759	Phase 1
0.7477	Intermediate Similarity	NPD1809	Phase 2
0.7477	Intermediate Similarity	NPD844	Approved
0.7458	Intermediate Similarity	NPD9493	Approved
0.7453	Intermediate Similarity	NPD5122	Clinical (unspecified phase)
0.7453	Intermediate Similarity	NPD845	Approved
0.7453	Intermediate Similarity	NPD1202	Approved
0.7431	Intermediate Similarity	NPD2066	Phase 3
0.7422	Intermediate Similarity	NPD1240	Approved
0.7419	Intermediate Similarity	NPD1203	Approved
0.7417	Intermediate Similarity	NPD1651	Approved
0.7405	Intermediate Similarity	NPD2935	Discontinued
0.7395	Intermediate Similarity	NPD5536	Phase 2
0.7395	Intermediate Similarity	NPD1758	Phase 1
0.7368	Intermediate Similarity	NPD6831	Clinical (unspecified phase)
0.736	Intermediate Similarity	NPD2798	Approved
0.735	Intermediate Similarity	NPD2228	Approved
0.735	Intermediate Similarity	NPD2234	Approved
0.735	Intermediate Similarity	NPD2229	Approved
0.7339	Intermediate Similarity	NPD1876	Approved
0.7333	Intermediate Similarity	NPD9256	Approved
0.7333	Intermediate Similarity	NPD9258	Approved
0.7328	Intermediate Similarity	NPD3299	Clinical (unspecified phase)
0.7328	Intermediate Similarity	NPD1510	Phase 2
0.7328	Intermediate Similarity	NPD2799	Discontinued
0.7321	Intermediate Similarity	NPD5909	Discontinued
0.7308	Intermediate Similarity	NPD1607	Approved
0.7288	Intermediate Similarity	NPD9281	Approved
0.7273	Intermediate Similarity	NPD5408	Approved
0.7273	Intermediate Similarity	NPD5406	Approved
0.7273	Intermediate Similarity	NPD5404	Approved
0.7273	Intermediate Similarity	NPD5405	Approved
0.7266	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7266	Intermediate Similarity	NPD6798	Discontinued
0.7265	Intermediate Similarity	NPD5535	Approved
0.7258	Intermediate Similarity	NPD1755	Approved
0.7248	Intermediate Similarity	NPD288	Approved
0.7244	Intermediate Similarity	NPD2614	Approved
0.7239	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7232	Intermediate Similarity	NPD9261	Approved
0.7232	Intermediate Similarity	NPD1931	Clinical (unspecified phase)
0.7232	Intermediate Similarity	NPD1930	Approved
0.7232	Intermediate Similarity	NPD1929	Approved
0.7218	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7218	Intermediate Similarity	NPD2344	Approved
0.7218	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7209	Intermediate Similarity	NPD6663	Approved
0.7209	Intermediate Similarity	NPD4062	Phase 3
0.7209	Intermediate Similarity	NPD6233	Phase 2
0.7207	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD1283	Approved
0.72	Intermediate Similarity	NPD3225	Approved
0.7197	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7193	Intermediate Similarity	NPD968	Approved
0.7185	Intermediate Similarity	NPD8166	Discontinued
0.7185	Intermediate Similarity	NPD3750	Approved
0.7182	Intermediate Similarity	NPD9495	Approved
0.7168	Intermediate Similarity	NPD9610	Approved
0.7168	Intermediate Similarity	NPD9608	Approved
0.7165	Intermediate Similarity	NPD5736	Approved
0.7164	Intermediate Similarity	NPD1549	Phase 2
0.7157	Intermediate Similarity	NPD9491	Approved
0.7143	Intermediate Similarity	NPD3266	Approved
0.7143	Intermediate Similarity	NPD5951	Approved
0.7143	Intermediate Similarity	NPD3267	Approved
0.7143	Intermediate Similarity	NPD7450	Phase 2
0.7132	Intermediate Similarity	NPD2313	Discontinued
0.713	Intermediate Similarity	NPD2342	Discontinued
0.7119	Intermediate Similarity	NPD7635	Approved
0.7103	Intermediate Similarity	NPD1239	Approved
0.7101	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD6355	Discontinued
0.7097	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7087	Intermediate Similarity	NPD258	Approved
0.7087	Intermediate Similarity	NPD257	Approved
0.7073	Intermediate Similarity	NPD5238	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD4628	Phase 3
0.7049	Intermediate Similarity	NPD3091	Approved
0.7049	Intermediate Similarity	NPD5304	Approved
0.7049	Intermediate Similarity	NPD5303	Approved
0.7043	Intermediate Similarity	NPD3134	Approved
0.704	Intermediate Similarity	NPD1608	Approved
0.704	Intermediate Similarity	NPD4878	Approved
0.704	Intermediate Similarity	NPD9269	Phase 2
0.704	Intermediate Similarity	NPD9717	Approved
0.7034	Intermediate Similarity	NPD6124	Clinical (unspecified phase)
0.7031	Intermediate Similarity	NPD9569	Approved
0.7029	Intermediate Similarity	NPD7390	Discontinued
0.7009	Intermediate Similarity	NPD4750	Phase 3
0.7009	Intermediate Similarity	NPD9380	Clinical (unspecified phase)
0.7009	Intermediate Similarity	NPD5451	Approved
0.7009	Intermediate Similarity	NPD1792	Phase 2
0.7007	Intermediate Similarity	NPD2309	Approved
0.7007	Intermediate Similarity	NPD6190	Approved
0.6992	Remote Similarity	NPD4093	Discontinued
0.6992	Remote Similarity	NPD9268	Approved
0.6991	Remote Similarity	NPD1932	Approved
0.6984	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.6983	Remote Similarity	NPD1358	Approved
0.6978	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD6832	Phase 2
0.6964	Remote Similarity	NPD1238	Approved
0.6961	Remote Similarity	NPD226	Approved
0.696	Remote Similarity	NPD1281	Approved
0.696	Remote Similarity	NPD422	Phase 1
0.6957	Remote Similarity	NPD7440	Discontinued
0.6952	Remote Similarity	NPD9257	Approved
0.6952	Remote Similarity	NPD9259	Approved
0.694	Remote Similarity	NPD4308	Phase 3
0.694	Remote Similarity	NPD651	Clinical (unspecified phase)
0.6939	Remote Similarity	NPD9087	Approved
0.6935	Remote Similarity	NPD4626	Approved
0.6935	Remote Similarity	NPD2286	Discontinued
0.6935	Remote Similarity	NPD4589	Approved
0.6935	Remote Similarity	NPD4059	Approved
0.6934	Remote Similarity	NPD3400	Discontinued
0.6934	Remote Similarity	NPD7003	Approved
0.693	Remote Similarity	NPD6647	Phase 2
0.6923	Remote Similarity	NPD2684	Approved
0.6923	Remote Similarity	NPD7095	Approved
0.6923	Remote Similarity	NPD3136	Phase 2
0.6917	Remote Similarity	NPD5283	Phase 1
0.6917	Remote Similarity	NPD7159	Clinical (unspecified phase)
0.6916	Remote Similarity	NPD800	Approved
0.6911	Remote Similarity	NPD1548	Phase 1
0.6909	Remote Similarity	NPD1693	Approved
0.6909	Remote Similarity	NPD688	Clinical (unspecified phase)
0.6906	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6906	Remote Similarity	NPD1511	Approved
0.6905	Remote Similarity	NPD2562	Approved
0.6905	Remote Similarity	NPD2561	Approved
0.6899	Remote Similarity	NPD4208	Discontinued
0.6899	Remote Similarity	NPD9494	Approved
0.6897	Remote Similarity	NPD1445	Approved
0.6897	Remote Similarity	NPD1444	Approved
0.6894	Remote Similarity	NPD826	Approved
0.6894	Remote Similarity	NPD825	Approved
0.6891	Remote Similarity	NPD228	Approved
0.6889	Remote Similarity	NPD1538	Phase 1
0.6889	Remote Similarity	NPD1519	Approved
0.6889	Remote Similarity	NPD1537	Approved
0.6887	Remote Similarity	NPD4793	Discontinued
0.6884	Remote Similarity	NPD2354	Approved
0.688	Remote Similarity	NPD3421	Phase 3
0.6875	Remote Similarity	NPD9273	Approved
0.6875	Remote Similarity	NPD4339	Clinical (unspecified phase)
0.6863	Remote Similarity	NPD1507	Clinical (unspecified phase)
0.6861	Remote Similarity	NPD2976	Clinical (unspecified phase)
0.686	Remote Similarity	NPD1476	Clinical (unspecified phase)
0.686	Remote Similarity	NPD690	Clinical (unspecified phase)
0.686	Remote Similarity	NPD2629	Approved
0.6853	Remote Similarity	NPD4380	Phase 2
0.6852	Remote Similarity	NPD1089	Approved
0.6852	Remote Similarity	NPD1090	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