NPASS Compound

Structure

CID128816 OpenBabel06191715482D 27 30 0 0 1 0 0 0 0 0999 V2000 -2.0046 -2.5509 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2786 -0.2186 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9340 -1.3103 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1550 -1.1708 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1360 -0.6179 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7571 -3.2601 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7398 -3.6458 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6619 -2.2022 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2751 -2.2724 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7345 -1.5303 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.3643 -0.7464 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.1913 -1.4258 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6919 -0.2880 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.9317 -3.9183 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5652 -2.9875 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4251 -1.5579 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.9143 -1.5836 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.9143 -1.5836 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.9143 -0.5279 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.0890 -4.9622 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0511 -3.5326 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.5479 -3.3732 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4078 -1.9436 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.8286 -2.1114 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -2.1114 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9143 -0.5279 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4 5 1 0 0 0 0 4 10 1 0 0 0 0 5 13 1 0 0 0 0 6 7 1 0 0 0 0 6 14 1 0 0 0 0 7 15 1 0 0 0 0 8 9 1 0 0 0 0 8 12 1 0 0 0 0 9 18 1 0 0 0 0 10 1 1 6 0 0 0 10 12 1 0 0 0 0 11 2 1 6 0 0 0 11 13 1 0 0 0 0 11 16 1 0 0 0 0 12 19 1 1 0 0 0 13 19 1 1 0 0 0 14 20 2 0 0 0 0 14 21 1 0 0 0 0 15 22 2 0 0 0 0 15 23 1 0 0 0 0 16 23 1 6 0 0 0 16 24 1 0 0 0 0 17 19 1 1 0 0 0 17 24 1 0 0 0 0 17 25 1 0 0 0 0 18 3 1 6 0 0 0 18 25 1 0 0 0 0 18 26 1 0 0 0 0 19 27 1 6 0 0 0 26 27 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	384.18
Volume:	368.003
LogP:	3.066
LogD:	2.114
LogS:	-4.047
# Rotatable Bonds:	5
TPSA:	100.52
# H-Bond Aceptor:	8
# H-Bond Donor:	1
# Rings:	5
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.583
Synthetic Accessibility Score:	5.668
Fsp3:	0.895
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.506
MDCK Permeability:	8.720009645912796e-05
Pgp-inhibitor:	0.943
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.002
20% Bioavailability (F20%):	0.004
30% Bioavailability (F30%):	0.129

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.354
Plasma Protein Binding (PPB):	65.88251495361328%
Volume Distribution (VD):	0.572
Pgp-substrate:	26.398696899414062%

ADMET: Metabolism

CYP1A2-inhibitor:	0.021
CYP1A2-substrate:	0.944
CYP2C19-inhibitor:	0.021
CYP2C19-substrate:	0.635
CYP2C9-inhibitor:	0.014
CYP2C9-substrate:	0.134
CYP2D6-inhibitor:	0.058
CYP2D6-substrate:	0.208
CYP3A4-inhibitor:	0.019
CYP3A4-substrate:	0.155

ADMET: Excretion

Clearance (CL):	8.663
Half-life (T1/2):	0.851

ADMET: Toxicity

hERG Blockers:	0.131
Human Hepatotoxicity (H-HT):	0.971
Drug-inuced Liver Injury (DILI):	0.936
AMES Toxicity:	0.887
Rat Oral Acute Toxicity:	0.299
Maximum Recommended Daily Dose:	0.163
Skin Sensitization:	0.496
Carcinogencity:	0.628
Eye Corrosion:	0.016
Eye Irritation:	0.042
Respiratory Toxicity:	0.963

Download Data

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

Natural Product: NPC128816

Natural Product ID:	NPC128816
*Common Name:**	FIHJKUPKCHIPAT-HXMLZIBGSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	FIHJKUPKCHIPAT-HXMLZIBGSA-N
Standard InCHI:	InChI=1S/C19H28O8/c1-10-4-5-13-11(2)16(23-15(22)7-6-14(20)21)24-17-19(13)12(10)8-9-18(3,25-17)26-27-19/h10-13,16-17H,4-9H2,1-3H3,(H,20,21)/t10-,11-,12+,13+,16+,17-,18+,19-/m1/s1
SMILES:	C[C@@H]1CC[C@H]2[C@@H](C)[C@@H](OC(=O)CCC(=O)O)O[C@H]3[C@]42[C@H]1CC[C@@](C)(O3)OO4
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3039774
PubChem CID:	156252
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001550] Sesquiterpenoids [CHEMONTID:0002440] Artemisinins

*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
NPO26589	Artemisia annua L.	Strain	Asteraceae	Eukaryota	n.a.	leaf	n.a.	DOI[10.1007/s11418-006-0112-9]
NPO26589	Artemisia annua L.	Strain	Asteraceae	Eukaryota	n.a.	stem	n.a.	DOI[10.1007/s11418-006-0112-9]
NPO26589	Artemisia annua L.	Strain	Asteraceae	Eukaryota	n.a.	flower	n.a.	DOI[10.1007/s11418-006-0112-9]
NPO26589	Artemisia annua L.	Strain	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[6387056]
NPO26589	Artemisia annua L.	Strain	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO10506	Artemisia apiacea	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26589	Artemisia annua L.	Strain	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10506	Artemisia apiacea	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26589	Artemisia annua L.	Strain	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO10506	Artemisia apiacea	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO26589	Artemisia annua L.	Strain	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO10506	Artemisia apiacea	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO10506	Artemisia apiacea	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26589	Artemisia annua L.	Strain	Asteraceae	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
EC50	3
IC50	7
Potency	9

Activity Type	# Activity
Individual Protein	4
NON-MOLECULAR	2
Organism	7
Others	6

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1197	Individual Protein	Huntingtin	Homo sapiens	Potency	=	3162.3	nM	PMID[542291]
NPT445	Individual Protein	Peripheral myelin protein 22	Rattus norvegicus	Potency	n.a.	2557.5	nM	PMID[542291]
NPT10	Individual Protein	Geminin	Homo sapiens	Potency	n.a.	33498.3	nM	PMID[542291]
NPT10	Individual Protein	Geminin	Homo sapiens	Potency	n.a.	13335.9	nM	PMID[542291]
NPT2	Others	Unspecified		EC50	>	120000.0	nM	PMID[542290]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	Potency	n.a.	1.3	nM	PMID[542291]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	Potency	n.a.	1.9	nM	PMID[542291]
NPT2	Others	Unspecified		Potency	n.a.	39.8	nM	PMID[542291]
NPT2	Others	Unspecified		Potency	n.a.	35.5	nM	PMID[542291]
NPT2	Others	Unspecified		Potency	n.a.	32196.8	nM	PMID[542291]
NPT844	Organism	Trypanosoma brucei rhodesiense	Trypanosoma brucei rhodesiense	IC50	=	16780.0	nM	PMID[542292]
NPT633	Organism	Leishmania donovani	Leishmania donovani	IC50	>	7800.0	nM	PMID[542292]
NPT580	Organism	Trypanosoma cruzi	Trypanosoma cruzi	IC50	=	8970.0	nM	PMID[542292]
NPT633	Organism	Leishmania donovani	Leishmania donovani	IC50	=	350.0	nM	PMID[542292]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	7800.0	nM	PMID[542292]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	780.0	nM	PMID[542292]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	3.0	nM	PMID[542292]

☑ 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 NPC128816 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	511
0.1-0.2	4109
0.2-0.3	12368
0.3-0.4	12870
0.4-0.5	6578
0.5-0.6	5112
0.6-0.7	1120
0.7-0.8	9
0.8-0.85	0
0.85-0.9	15
0.9-0.95	0
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC67158
1.0	High Similarity	NPC30102
0.8765	High Similarity	NPC285480
0.8765	High Similarity	NPC30443
0.8765	High Similarity	NPC45256
0.8765	High Similarity	NPC260977
0.859	High Similarity	NPC200167
0.859	High Similarity	NPC209666
0.859	High Similarity	NPC53868
0.859	High Similarity	NPC31046
0.8442	Intermediate Similarity	NPC29005
0.8442	Intermediate Similarity	NPC51956
0.8442	Intermediate Similarity	NPC5209
0.8193	Intermediate Similarity	NPC60568
0.764	Intermediate Similarity	NPC471411
0.764	Intermediate Similarity	NPC471410
0.7529	Intermediate Similarity	NPC177343
0.7474	Intermediate Similarity	NPC148872
0.747	Intermediate Similarity	NPC166250
0.7368	Intermediate Similarity	NPC94582
0.7368	Intermediate Similarity	NPC57964
0.7349	Intermediate Similarity	NPC123122
0.734	Intermediate Similarity	NPC475307
0.7326	Intermediate Similarity	NPC272841
0.7303	Intermediate Similarity	NPC241959
0.7292	Intermediate Similarity	NPC237071
0.7292	Intermediate Similarity	NPC475765
0.7292	Intermediate Similarity	NPC238796
0.7292	Intermediate Similarity	NPC203434
0.7283	Intermediate Similarity	NPC470872
0.7263	Intermediate Similarity	NPC151214
0.7263	Intermediate Similarity	NPC191915
0.7253	Intermediate Similarity	NPC474008
0.7253	Intermediate Similarity	NPC476717
0.7222	Intermediate Similarity	NPC18953
0.7216	Intermediate Similarity	NPC472273
0.7209	Intermediate Similarity	NPC476719
0.7188	Intermediate Similarity	NPC215570
0.7159	Intermediate Similarity	NPC471216
0.7159	Intermediate Similarity	NPC471217
0.7157	Intermediate Similarity	NPC203974
0.7143	Intermediate Similarity	NPC471375
0.7143	Intermediate Similarity	NPC209798
0.7143	Intermediate Similarity	NPC235402
0.7143	Intermediate Similarity	NPC471374
0.7126	Intermediate Similarity	NPC252483
0.7126	Intermediate Similarity	NPC191345
0.7113	Intermediate Similarity	NPC296936
0.7113	Intermediate Similarity	NPC252056
0.7113	Intermediate Similarity	NPC475785
0.7111	Intermediate Similarity	NPC474284
0.7111	Intermediate Similarity	NPC475820
0.7111	Intermediate Similarity	NPC213737
0.7111	Intermediate Similarity	NPC474253
0.7111	Intermediate Similarity	NPC474346
0.7108	Intermediate Similarity	NPC471879
0.71	Intermediate Similarity	NPC80640
0.7097	Intermediate Similarity	NPC221993
0.7087	Intermediate Similarity	NPC207693
0.7083	Intermediate Similarity	NPC178949
0.7083	Intermediate Similarity	NPC96736
0.7079	Intermediate Similarity	NPC116320
0.7079	Intermediate Similarity	NPC71541
0.7079	Intermediate Similarity	NPC211049
0.7079	Intermediate Similarity	NPC119922
0.7071	Intermediate Similarity	NPC471428
0.7071	Intermediate Similarity	NPC471427
0.7071	Intermediate Similarity	NPC51579
0.7071	Intermediate Similarity	NPC471426
0.7065	Intermediate Similarity	NPC470657
0.7059	Intermediate Similarity	NPC308489
0.7053	Intermediate Similarity	NPC475878
0.7041	Intermediate Similarity	NPC470591
0.7041	Intermediate Similarity	NPC266417
0.7033	Intermediate Similarity	NPC79308
0.7021	Intermediate Similarity	NPC131466
0.7019	Intermediate Similarity	NPC228190
0.7019	Intermediate Similarity	NPC236753
0.7019	Intermediate Similarity	NPC22709
0.7	Intermediate Similarity	NPC2096
0.7	Intermediate Similarity	NPC208912
0.7	Intermediate Similarity	NPC476838
0.7	Intermediate Similarity	NPC472081
0.7	Intermediate Similarity	NPC476839
0.7	Intermediate Similarity	NPC475574
0.7	Intermediate Similarity	NPC476512
0.7	Intermediate Similarity	NPC108227
0.699	Remote Similarity	NPC126753
0.6989	Remote Similarity	NPC213658
0.6989	Remote Similarity	NPC62202
0.6989	Remote Similarity	NPC45833
0.6989	Remote Similarity	NPC31349
0.6989	Remote Similarity	NPC110365
0.6989	Remote Similarity	NPC43912
0.6989	Remote Similarity	NPC140446
0.6961	Remote Similarity	NPC469827
0.6961	Remote Similarity	NPC267637
0.6957	Remote Similarity	NPC476715
0.6957	Remote Similarity	NPC290612
0.6952	Remote Similarity	NPC470622
0.6941	Remote Similarity	NPC476718
0.6932	Remote Similarity	NPC43463
0.6931	Remote Similarity	NPC470029
0.6931	Remote Similarity	NPC114700
0.6931	Remote Similarity	NPC310138
0.6931	Remote Similarity	NPC471254
0.6931	Remote Similarity	NPC134967
0.6923	Remote Similarity	NPC474266
0.6923	Remote Similarity	NPC469826
0.69	Remote Similarity	NPC80417
0.69	Remote Similarity	NPC20028
0.6897	Remote Similarity	NPC107963
0.6897	Remote Similarity	NPC136424
0.6893	Remote Similarity	NPC273189
0.6893	Remote Similarity	NPC184805
0.6889	Remote Similarity	NPC476494
0.6889	Remote Similarity	NPC470156
0.6889	Remote Similarity	NPC470154
0.6887	Remote Similarity	NPC469824
0.6882	Remote Similarity	NPC107603
0.6882	Remote Similarity	NPC268633
0.6875	Remote Similarity	NPC307167
0.6875	Remote Similarity	NPC210759
0.6875	Remote Similarity	NPC229801
0.6869	Remote Similarity	NPC74466
0.6869	Remote Similarity	NPC210157
0.6863	Remote Similarity	NPC139181
0.6863	Remote Similarity	NPC34562
0.6863	Remote Similarity	NPC97260
0.6863	Remote Similarity	NPC471253
0.6863	Remote Similarity	NPC476837
0.6854	Remote Similarity	NPC170595
0.6842	Remote Similarity	NPC82955
0.6837	Remote Similarity	NPC21897
0.6832	Remote Similarity	NPC478181
0.6832	Remote Similarity	NPC280991
0.6832	Remote Similarity	NPC477172
0.6827	Remote Similarity	NPC471430
0.6827	Remote Similarity	NPC293512
0.6822	Remote Similarity	NPC470543
0.6822	Remote Similarity	NPC477489
0.6822	Remote Similarity	NPC157571
0.6818	Remote Similarity	NPC474003
0.6813	Remote Similarity	NPC477447
0.6813	Remote Similarity	NPC216800
0.6813	Remote Similarity	NPC470155
0.6813	Remote Similarity	NPC475849
0.6813	Remote Similarity	NPC477446
0.6809	Remote Similarity	NPC472396
0.6804	Remote Similarity	NPC323231
0.6804	Remote Similarity	NPC224003
0.6804	Remote Similarity	NPC470623
0.6804	Remote Similarity	NPC18724
0.6804	Remote Similarity	NPC171741
0.68	Remote Similarity	NPC292775
0.6796	Remote Similarity	NPC470167
0.6792	Remote Similarity	NPC471431
0.6778	Remote Similarity	NPC186594
0.6778	Remote Similarity	NPC125366
0.6778	Remote Similarity	NPC472951
0.6778	Remote Similarity	NPC472943
0.6778	Remote Similarity	NPC475456
0.6774	Remote Similarity	NPC477205
0.6771	Remote Similarity	NPC470114
0.6771	Remote Similarity	NPC50443
0.6771	Remote Similarity	NPC65550
0.6771	Remote Similarity	NPC18536
0.6771	Remote Similarity	NPC279329
0.6768	Remote Similarity	NPC193785
0.6765	Remote Similarity	NPC310031
0.6765	Remote Similarity	NPC80191
0.6765	Remote Similarity	NPC470172
0.6762	Remote Similarity	NPC472079
0.6759	Remote Similarity	NPC204458
0.6759	Remote Similarity	NPC189884
0.6759	Remote Similarity	NPC47063
0.6759	Remote Similarity	NPC138334
0.6747	Remote Similarity	NPC477758
0.6747	Remote Similarity	NPC477760
0.6747	Remote Similarity	NPC477759
0.6747	Remote Similarity	NPC477754
0.6747	Remote Similarity	NPC476928
0.6747	Remote Similarity	NPC477761
0.6742	Remote Similarity	NPC477577
0.6739	Remote Similarity	NPC470070
0.6737	Remote Similarity	NPC471221
0.6737	Remote Similarity	NPC476379
0.6737	Remote Similarity	NPC281004
0.6737	Remote Similarity	NPC470009
0.6735	Remote Similarity	NPC267238
0.6735	Remote Similarity	NPC252253
0.6735	Remote Similarity	NPC253611
0.6735	Remote Similarity	NPC77717
0.6735	Remote Similarity	NPC309866
0.6735	Remote Similarity	NPC45959
0.6735	Remote Similarity	NPC305418
0.6735	Remote Similarity	NPC471373
0.6735	Remote Similarity	NPC148593
0.6735	Remote Similarity	NPC211238
0.6733	Remote Similarity	NPC41843

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 NPC128816 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	564
0.1-0.2	4084
0.2-0.3	3141
0.3-0.4	832
0.4-0.5	376
0.5-0.6	131
0.6-0.7	13
0.7-0.8	0
0.8-0.85	0
0.85-0.9	7
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Drug ID	Developmental Stage
1.0	High Similarity	NPD3669	Approved
1.0	High Similarity	NPD3670	Clinical (unspecified phase)
0.8765	High Similarity	NPD1780	Approved
0.8765	High Similarity	NPD1779	Approved
0.859	High Similarity	NPD1810	Approved
0.859	High Similarity	NPD1811	Approved
0.8442	Intermediate Similarity	NPD2687	Approved
0.8442	Intermediate Similarity	NPD2254	Approved
0.8442	Intermediate Similarity	NPD2686	Approved
0.6857	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6512	Remote Similarity	NPD7532	Clinical (unspecified phase)
0.6476	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6465	Remote Similarity	NPD8171	Discontinued
0.6455	Remote Similarity	NPD8133	Approved
0.6429	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6222	Remote Similarity	NPD3702	Approved
0.6196	Remote Similarity	NPD6697	Approved
0.6196	Remote Similarity	NPD6114	Approved
0.6196	Remote Similarity	NPD6118	Approved
0.6196	Remote Similarity	NPD6115	Approved
0.619	Remote Similarity	NPD371	Approved
0.6147	Remote Similarity	NPD6686	Approved
0.6132	Remote Similarity	NPD8138	Approved
0.6132	Remote Similarity	NPD8084	Approved
0.6132	Remote Similarity	NPD8139	Approved
0.6132	Remote Similarity	NPD8083	Approved
0.6132	Remote Similarity	NPD8085	Approved
0.6132	Remote Similarity	NPD8082	Approved
0.6132	Remote Similarity	NPD8086	Approved
0.6111	Remote Similarity	NPD8393	Approved
0.6102	Remote Similarity	NPD8328	Phase 3
0.6087	Remote Similarity	NPD6116	Phase 1
0.6075	Remote Similarity	NPD8275	Approved
0.6075	Remote Similarity	NPD8276	Approved
0.6064	Remote Similarity	NPD6928	Phase 2
0.6036	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6019	Remote Similarity	NPD3710	Phase 2
0.6019	Remote Similarity	NPD8081	Approved
0.6	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.5983	Remote Similarity	NPD8294	Approved
0.5983	Remote Similarity	NPD8377	Approved
0.5978	Remote Similarity	NPD6117	Approved
0.5948	Remote Similarity	NPD7328	Approved
0.5948	Remote Similarity	NPD7327	Approved
0.5932	Remote Similarity	NPD8296	Approved
0.5932	Remote Similarity	NPD8033	Approved
0.5932	Remote Similarity	NPD8380	Approved
0.5932	Remote Similarity	NPD8378	Approved
0.5932	Remote Similarity	NPD8335	Approved
0.5932	Remote Similarity	NPD8379	Approved
0.5913	Remote Similarity	NPD6940	Discontinued
0.5909	Remote Similarity	NPD6412	Phase 2
0.5897	Remote Similarity	NPD7516	Approved
0.5882	Remote Similarity	NPD8035	Phase 2
0.5882	Remote Similarity	NPD8034	Phase 2
0.5868	Remote Similarity	NPD7507	Approved
0.5851	Remote Similarity	NPD4802	Phase 2
0.5851	Remote Similarity	NPD4238	Approved
0.5798	Remote Similarity	NPD8516	Approved
0.5798	Remote Similarity	NPD8517	Approved
0.5798	Remote Similarity	NPD7503	Approved
0.5798	Remote Similarity	NPD8515	Approved
0.5798	Remote Similarity	NPD8513	Phase 3
0.5789	Remote Similarity	NPD7329	Approved
0.5766	Remote Similarity	NPD8140	Approved
0.5766	Remote Similarity	NPD8307	Discontinued
0.5766	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.5761	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.5741	Remote Similarity	NPD1700	Approved
0.5726	Remote Similarity	NPD7319	Approved
0.5699	Remote Similarity	NPD3703	Phase 2
0.5682	Remote Similarity	NPD4224	Phase 2
0.5679	Remote Similarity	NPD615	Clinical (unspecified phase)
0.5664	Remote Similarity	NPD8305	Approved
0.5664	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.5664	Remote Similarity	NPD8306	Approved
0.5618	Remote Similarity	NPD897	Approved
0.5618	Remote Similarity	NPD896	Approved
0.5618	Remote Similarity	NPD898	Approved
0.5614	Remote Similarity	NPD8087	Discontinued
0.5607	Remote Similarity	NPD7902	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