NPASS Compound

Structure

CID120172 OpenBabel06191715472D 34 38 0 0 1 0 0 0 0 0999 V2000 -3.6808 -1.7024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8147 -0.2024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0823 -0.1615 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9013 -1.8841 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5468 -1.2024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6808 0.2976 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0768 -0.2661 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8958 -1.9886 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9487 -1.7024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7044 -3.2564 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9898 -2.8963 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4546 -4.5436 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6473 0.5352 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3601 1.6942 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8147 -1.2024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4945 -0.9706 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0388 -2.5873 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5468 -0.2024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4836 -1.1796 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4965 -4.2346 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1977 -3.8745 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3383 1.4863 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0827 -1.2024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9781 -0.2079 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3090 0.9511 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1691 -1.6092 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.5000 -0.8660 0.0000 C 0 0 1 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 -5.4128 0.2976 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.4781 -1.2841 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2396 -4.9037 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.1488 -4.1835 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.0074 2.2294 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.2872 1.1590 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 5 1 0 0 0 0 1 15 2 0 0 0 0 2 6 2 0 0 0 0 2 15 1 0 0 0 0 3 7 1 0 0 0 0 3 16 2 0 0 0 0 4 8 2 0 0 0 0 4 16 1 0 0 0 0 5 18 2 0 0 0 0 6 18 1 0 0 0 0 7 19 2 0 0 0 0 8 19 1 0 0 0 0 9 15 1 0 0 0 0 9 23 2 0 0 0 0 10 17 2 0 0 0 0 10 20 1 0 0 0 0 11 17 1 0 0 0 0 11 21 2 0 0 0 0 12 20 2 0 0 0 0 12 21 1 0 0 0 0 13 22 2 0 0 0 0 13 24 1 0 0 0 0 14 22 1 0 0 0 0 14 25 2 0 0 0 0 18 29 1 0 0 0 0 19 30 1 0 0 0 0 20 31 1 0 0 0 0 21 32 1 0 0 0 0 22 33 1 0 0 0 0 23 24 1 0 0 0 0 23 26 1 0 0 0 0 24 28 2 0 0 0 0 25 28 1 0 0 0 0 25 34 1 0 0 0 0 26 17 1 6 0 0 0 26 27 1 0 0 0 0 27 16 1 1 0 0 0 27 28 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	454.14
Volume:	468.529
LogP:	4.715
LogD:	3.674
LogS:	-4.523
# Rotatable Bonds:	3
TPSA:	121.38
# H-Bond Aceptor:	6
# H-Bond Donor:	6
# Rings:	5
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.247
Synthetic Accessibility Score:	3.614
Fsp3:	0.071
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.973
MDCK Permeability:	7.0890469032747205e-06
Pgp-inhibitor:	0.888
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.133
20% Bioavailability (F20%):	1.0
30% Bioavailability (F30%):	0.997

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.023
Plasma Protein Binding (PPB):	98.99118041992188%
Volume Distribution (VD):	0.503
Pgp-substrate:	2.659620761871338%

ADMET: Metabolism

CYP1A2-inhibitor:	0.875
CYP1A2-substrate:	0.194
CYP2C19-inhibitor:	0.813
CYP2C19-substrate:	0.046
CYP2C9-inhibitor:	0.802
CYP2C9-substrate:	0.981
CYP2D6-inhibitor:	0.46
CYP2D6-substrate:	0.743
CYP3A4-inhibitor:	0.806
CYP3A4-substrate:	0.145

ADMET: Excretion

Clearance (CL):	11.58
Half-life (T1/2):	0.832

ADMET: Toxicity

hERG Blockers:	0.307
Human Hepatotoxicity (H-HT):	0.19
Drug-inuced Liver Injury (DILI):	0.046
AMES Toxicity:	0.274
Rat Oral Acute Toxicity:	0.368
Maximum Recommended Daily Dose:	0.975
Skin Sensitization:	0.955
Carcinogencity:	0.039
Eye Corrosion:	0.003
Eye Irritation:	0.873
Respiratory Toxicity:	0.279

Download Data

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

Natural Product: NPC120172

Natural Product ID:	NPC120172
*Common Name:**	Quadrangularin A
IUPAC Name:	(1E,2R,3R)-2-(3,5-dihydroxyphenyl)-3-(4-hydroxyphenyl)-1-[(4-hydroxyphenyl)methylidene]-2,3-dihydroindene-4,6-diol
Synonyms:	(+/-)-Quadrangularin A
Standard InCHIKey:	BIQMSWPBPAKGSE-PBSLAQMISA-N
Standard InCHI:	InChI=1S/C28H22O6/c29-18-5-1-15(2-6-18)9-23-24-13-22(33)14-25(34)28(24)27(16-3-7-19(30)8-4-16)26(23)17-10-20(31)12-21(32)11-17/h1-14,26-27,29-34H/b23-9-/t26-,27+/m1/s1
SMILES:	Oc1ccc(cc1)/C=C1/c2cc(O)cc(c2[C@H]([C@@H]1c1cc(O)cc(c1)O)c1ccc(cc1)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2335820
PubChem CID:	5318096
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000253] Stilbenes

*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
NPO2251	Sphagneticola trilobata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22574649]
NPO22302	Murraya microphylla	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26594776]
NPO2251	Sphagneticola trilobata	Species	Asteraceae	Eukaryota	n.a.	whole plant	n.a.	PMID[26946839]
NPO22302	Murraya microphylla	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[30381950]
NPO2251	Sphagneticola trilobata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[33306388]
NPO22302	Murraya microphylla	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO22302	Murraya microphylla	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5271.1	Ampelopsis glandulosa var. brevipedunculata	Varieties	Vitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22302	Murraya microphylla	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO22302	Murraya microphylla	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21593	Vulpes vulpes	Species	Canidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5271.1	Ampelopsis glandulosa var. brevipedunculata	Varieties	Vitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20083	Perezia recurvata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21847	Lecanora vinetorum	Species	Lecanoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2251	Sphagneticola trilobata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20519	Cytisus striatus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20892	Glochidion wrightii	Species	Phyllanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19961	Corydalis humosa	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20199	Euphorbia tortilis	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22751	Gentiana flavo-maculata	Species	Gentianaceae	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
Others	6

Activity Type	# Activity
Cell Line	1
Individual Protein	4
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT113	Cell Line	RAW264.7	Mus musculus	Inhibition	=	70.0	%	PMID[465787]
NPT108	Individual Protein	Estrogen receptor alpha	Homo sapiens	FC	=	0.92	n.a.	PMID[465788]
NPT108	Individual Protein	Estrogen receptor alpha	Homo sapiens	Activity	=	20.85	%	PMID[465788]
NPT248	Individual Protein	Estrogen receptor beta	Homo sapiens	FC	=	1.09	n.a.	PMID[465788]
NPT248	Individual Protein	Estrogen receptor beta	Homo sapiens	Activity	=	0.0	%	PMID[465788]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	57.93	%	PMID[465786]

☑ 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 NPC120172 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	453
0.1-0.2	1913
0.2-0.3	4683
0.3-0.4	13340
0.4-0.5	5775
0.5-0.6	7149
0.6-0.7	7509
0.7-0.8	1659
0.8-0.85	173
0.85-0.9	33
0.9-0.95	6
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9829	High Similarity	NPC97578
0.9664	High Similarity	NPC145659
0.9664	High Similarity	NPC9292
0.9274	High Similarity	NPC237424
0.9274	High Similarity	NPC238168
0.9237	High Similarity	NPC69006
0.9127	High Similarity	NPC473665
0.8898	High Similarity	NPC261973
0.881	High Similarity	NPC471519
0.881	High Similarity	NPC471518
0.8779	High Similarity	NPC20210
0.8729	High Similarity	NPC107240
0.8672	High Similarity	NPC473309
0.8667	High Similarity	NPC470760
0.8655	High Similarity	NPC246760
0.8655	High Similarity	NPC84999
0.8621	High Similarity	NPC202647
0.8594	High Similarity	NPC254000
0.8583	High Similarity	NPC115808
0.8582	High Similarity	NPC277784
0.8559	High Similarity	NPC43525
0.855	High Similarity	NPC15109
0.855	High Similarity	NPC11727
0.8522	High Similarity	NPC248904
0.8512	High Similarity	NPC299180
0.8492	Intermediate Similarity	NPC113495
0.8475	Intermediate Similarity	NPC476632
0.8475	Intermediate Similarity	NPC165770
0.8475	Intermediate Similarity	NPC225679
0.8475	Intermediate Similarity	NPC4493
0.8475	Intermediate Similarity	NPC224527
0.8435	Intermediate Similarity	NPC474839
0.8435	Intermediate Similarity	NPC292452
0.8403	Intermediate Similarity	NPC166995
0.8385	Intermediate Similarity	NPC471517
0.8385	Intermediate Similarity	NPC282508
0.8374	Intermediate Similarity	NPC217174
0.8362	Intermediate Similarity	NPC109691
0.8362	Intermediate Similarity	NPC470700
0.8362	Intermediate Similarity	NPC118286
0.8362	Intermediate Similarity	NPC39664
0.8362	Intermediate Similarity	NPC302681
0.8362	Intermediate Similarity	NPC39097
0.8348	Intermediate Similarity	NPC30506
0.8348	Intermediate Similarity	NPC119860
0.8348	Intermediate Similarity	NPC241891
0.8348	Intermediate Similarity	NPC102216
0.8333	Intermediate Similarity	NPC23804
0.8333	Intermediate Similarity	NPC322239
0.8333	Intermediate Similarity	NPC117846
0.832	Intermediate Similarity	NPC237667
0.8308	Intermediate Similarity	NPC472369
0.8305	Intermediate Similarity	NPC19808
0.8305	Intermediate Similarity	NPC33728
0.8296	Intermediate Similarity	NPC213607
0.8296	Intermediate Similarity	NPC174787
0.8296	Intermediate Similarity	NPC182509
0.8293	Intermediate Similarity	NPC206
0.8291	Intermediate Similarity	NPC54844
0.8276	Intermediate Similarity	NPC246056
0.8276	Intermediate Similarity	NPC134829
0.8271	Intermediate Similarity	NPC258780
0.8271	Intermediate Similarity	NPC125579
0.8271	Intermediate Similarity	NPC37410
0.8268	Intermediate Similarity	NPC224342
0.8264	Intermediate Similarity	NPC249270
0.825	Intermediate Similarity	NPC473521
0.8244	Intermediate Similarity	NPC8899
0.8235	Intermediate Similarity	NPC475018
0.822	Intermediate Similarity	NPC11554
0.822	Intermediate Similarity	NPC61885
0.822	Intermediate Similarity	NPC63698
0.822	Intermediate Similarity	NPC174981
0.8209	Intermediate Similarity	NPC133463
0.8209	Intermediate Similarity	NPC472648
0.8209	Intermediate Similarity	NPC472647
0.8209	Intermediate Similarity	NPC472649
0.8209	Intermediate Similarity	NPC141717
0.8209	Intermediate Similarity	NPC191462
0.8209	Intermediate Similarity	NPC206525
0.8209	Intermediate Similarity	NPC170328
0.819	Intermediate Similarity	NPC254965
0.819	Intermediate Similarity	NPC327811
0.8189	Intermediate Similarity	NPC53567
0.8182	Intermediate Similarity	NPC469611
0.8182	Intermediate Similarity	NPC715
0.8182	Intermediate Similarity	NPC261343
0.8182	Intermediate Similarity	NPC263753
0.8175	Intermediate Similarity	NPC39029
0.8174	Intermediate Similarity	NPC100340
0.8174	Intermediate Similarity	NPC143659
0.8167	Intermediate Similarity	NPC95716
0.8167	Intermediate Similarity	NPC322753
0.816	Intermediate Similarity	NPC472071
0.8156	Intermediate Similarity	NPC177172
0.8156	Intermediate Similarity	NPC122980
0.8156	Intermediate Similarity	NPC148516
0.8156	Intermediate Similarity	NPC107862
0.8156	Intermediate Similarity	NPC180605
0.8151	Intermediate Similarity	NPC186385
0.8151	Intermediate Similarity	NPC299568
0.8148	Intermediate Similarity	NPC71465
0.8148	Intermediate Similarity	NPC476393
0.8148	Intermediate Similarity	NPC472646
0.8145	Intermediate Similarity	NPC144343
0.814	Intermediate Similarity	NPC170485
0.812	Intermediate Similarity	NPC469610
0.8116	Intermediate Similarity	NPC173203
0.8116	Intermediate Similarity	NPC163508
0.8103	Intermediate Similarity	NPC168393
0.8099	Intermediate Similarity	NPC218801
0.8099	Intermediate Similarity	NPC46940
0.8095	Intermediate Similarity	NPC102639
0.8095	Intermediate Similarity	NPC328504
0.8087	Intermediate Similarity	NPC10588
0.8087	Intermediate Similarity	NPC248573
0.8087	Intermediate Similarity	NPC161571
0.8087	Intermediate Similarity	NPC275053
0.8083	Intermediate Similarity	NPC224870
0.8065	Intermediate Similarity	NPC277588
0.8058	Intermediate Similarity	NPC15659
0.8058	Intermediate Similarity	NPC304894
0.8051	Intermediate Similarity	NPC271274
0.8049	Intermediate Similarity	NPC469719
0.8049	Intermediate Similarity	NPC472893
0.8042	Intermediate Similarity	NPC157081
0.8042	Intermediate Similarity	NPC105073
0.8042	Intermediate Similarity	NPC233886
0.8042	Intermediate Similarity	NPC224528
0.8033	Intermediate Similarity	NPC321589
0.8031	Intermediate Similarity	NPC475166
0.8029	Intermediate Similarity	NPC472092
0.8029	Intermediate Similarity	NPC273623
0.8029	Intermediate Similarity	NPC472091
0.8029	Intermediate Similarity	NPC472090
0.8017	Intermediate Similarity	NPC268032
0.8017	Intermediate Similarity	NPC284011
0.8017	Intermediate Similarity	NPC151537
0.8017	Intermediate Similarity	NPC72947
0.8016	Intermediate Similarity	NPC68339
0.8016	Intermediate Similarity	NPC223451
0.8015	Intermediate Similarity	NPC94994
0.8015	Intermediate Similarity	NPC311293
0.8015	Intermediate Similarity	NPC148366
0.8015	Intermediate Similarity	NPC215300
0.8	Intermediate Similarity	NPC9592
0.8	Intermediate Similarity	NPC48781
0.8	Intermediate Similarity	NPC472370
0.8	Intermediate Similarity	NPC149633
0.8	Intermediate Similarity	NPC314187
0.7986	Intermediate Similarity	NPC473018
0.7986	Intermediate Similarity	NPC120633
0.7984	Intermediate Similarity	NPC137496
0.7984	Intermediate Similarity	NPC228503
0.7984	Intermediate Similarity	NPC138248
0.7984	Intermediate Similarity	NPC257540
0.7984	Intermediate Similarity	NPC474387
0.7984	Intermediate Similarity	NPC154511
0.7984	Intermediate Similarity	NPC474358
0.7984	Intermediate Similarity	NPC247858
0.7983	Intermediate Similarity	NPC232523
0.7983	Intermediate Similarity	NPC158253
0.7983	Intermediate Similarity	NPC204901
0.7971	Intermediate Similarity	NPC472089
0.7969	Intermediate Similarity	NPC71094
0.7967	Intermediate Similarity	NPC195922
0.7966	Intermediate Similarity	NPC37802
0.7953	Intermediate Similarity	NPC24125
0.7949	Intermediate Similarity	NPC249828
0.7949	Intermediate Similarity	NPC53051
0.7949	Intermediate Similarity	NPC85479
0.7949	Intermediate Similarity	NPC168303
0.7949	Intermediate Similarity	NPC24404
0.7949	Intermediate Similarity	NPC94351
0.7949	Intermediate Similarity	NPC71002
0.7949	Intermediate Similarity	NPC106396
0.7949	Intermediate Similarity	NPC313030
0.7949	Intermediate Similarity	NPC302219
0.7949	Intermediate Similarity	NPC222522
0.7949	Intermediate Similarity	NPC146798
0.7949	Intermediate Similarity	NPC242342
0.7943	Intermediate Similarity	NPC176804
0.7943	Intermediate Similarity	NPC71686
0.7939	Intermediate Similarity	NPC473221
0.7939	Intermediate Similarity	NPC53781
0.7937	Intermediate Similarity	NPC151197
0.7937	Intermediate Similarity	NPC191866
0.7934	Intermediate Similarity	NPC13482
0.7934	Intermediate Similarity	NPC141782
0.7931	Intermediate Similarity	NPC166761
0.7929	Intermediate Similarity	NPC295712
0.7929	Intermediate Similarity	NPC451542
0.7929	Intermediate Similarity	NPC313047
0.7929	Intermediate Similarity	NPC474203
0.7926	Intermediate Similarity	NPC476617
0.7926	Intermediate Similarity	NPC476616
0.7926	Intermediate Similarity	NPC476615
0.7926	Intermediate Similarity	NPC256307
0.7926	Intermediate Similarity	NPC66840
0.7926	Intermediate Similarity	NPC473107

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 NPC120172 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	389
0.1-0.2	1021
0.2-0.3	1310
0.3-0.4	3181
0.4-0.5	1788
0.5-0.6	1080
0.6-0.7	335
0.7-0.8	41
0.8-0.85	5
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8151	Intermediate Similarity	NPD4750	Phase 3
0.8087	Intermediate Similarity	NPD1242	Phase 1
0.8017	Intermediate Similarity	NPD940	Approved
0.8017	Intermediate Similarity	NPD846	Approved
0.8015	Intermediate Similarity	NPD4908	Phase 1
0.7895	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7874	Intermediate Similarity	NPD4059	Approved
0.7857	Intermediate Similarity	NPD3091	Approved
0.7845	Intermediate Similarity	NPD3020	Approved
0.7833	Intermediate Similarity	NPD2342	Discontinued
0.7786	Intermediate Similarity	NPD3094	Phase 2
0.7752	Intermediate Similarity	NPD3092	Approved
0.7734	Intermediate Similarity	NPD3019	Approved
0.7705	Intermediate Similarity	NPD3022	Approved
0.7705	Intermediate Similarity	NPD3021	Approved
0.7652	Intermediate Similarity	NPD4339	Clinical (unspecified phase)
0.7626	Intermediate Similarity	NPD5404	Approved
0.7626	Intermediate Similarity	NPD5408	Approved
0.7626	Intermediate Similarity	NPD5405	Approved
0.7626	Intermediate Similarity	NPD5406	Approved
0.7622	Intermediate Similarity	NPD7390	Discontinued
0.7615	Intermediate Similarity	NPD1610	Phase 2
0.7597	Intermediate Similarity	NPD2932	Approved
0.7597	Intermediate Similarity	NPD3095	Discontinued
0.7586	Intermediate Similarity	NPD2859	Approved
0.7586	Intermediate Similarity	NPD2860	Approved
0.7556	Intermediate Similarity	NPD4625	Phase 3
0.7537	Intermediate Similarity	NPD2861	Phase 2
0.752	Intermediate Similarity	NPD7635	Approved
0.75	Intermediate Similarity	NPD2934	Approved
0.75	Intermediate Similarity	NPD2933	Approved
0.7385	Intermediate Similarity	NPD4093	Discontinued
0.7373	Intermediate Similarity	NPD288	Approved
0.7368	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD4749	Approved
0.7353	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7328	Intermediate Similarity	NPD2286	Discontinued
0.7308	Intermediate Similarity	NPD1548	Phase 1
0.7305	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7292	Intermediate Similarity	NPD3892	Phase 2
0.7288	Intermediate Similarity	NPD844	Approved
0.7279	Intermediate Similarity	NPD5736	Approved
0.7279	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD3026	Approved
0.7273	Intermediate Similarity	NPD3023	Approved
0.7252	Intermediate Similarity	NPD3025	Approved
0.7252	Intermediate Similarity	NPD3024	Approved
0.7218	Intermediate Similarity	NPD1201	Approved
0.7206	Intermediate Similarity	NPD4624	Approved
0.7203	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.7174	Intermediate Similarity	NPD3027	Phase 3
0.7143	Intermediate Similarity	NPD1613	Approved
0.7143	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7132	Intermediate Similarity	NPD1470	Approved
0.7119	Intermediate Similarity	NPD845	Approved
0.708	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7071	Intermediate Similarity	NPD6663	Approved
0.7063	Intermediate Similarity	NPD3299	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD3750	Approved
0.7054	Intermediate Similarity	NPD4869	Clinical (unspecified phase)
0.7042	Intermediate Similarity	NPD4097	Suspended
0.7021	Intermediate Similarity	NPD943	Approved
0.7008	Intermediate Similarity	NPD1792	Phase 2
0.7006	Intermediate Similarity	NPD7199	Phase 2
0.7	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD1809	Phase 2
0.7	Intermediate Similarity	NPD3764	Approved
0.698	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6929	Remote Similarity	NPD5156	Approved
0.6929	Remote Similarity	NPD5155	Approved
0.6923	Remote Similarity	NPD2228	Approved
0.6923	Remote Similarity	NPD2229	Approved
0.6923	Remote Similarity	NPD2234	Approved
0.6918	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD7037	Approved
0.6917	Remote Similarity	NPD7741	Discontinued
0.6913	Remote Similarity	NPD7041	Phase 2
0.6913	Remote Similarity	NPD7040	Clinical (unspecified phase)
0.6901	Remote Similarity	NPD3620	Phase 2
0.6901	Remote Similarity	NPD4060	Phase 1
0.6901	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD6099	Approved
0.6897	Remote Similarity	NPD6100	Approved
0.6894	Remote Similarity	NPD7325	Clinical (unspecified phase)
0.687	Remote Similarity	NPD1476	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD7447	Phase 1
0.6867	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6861	Remote Similarity	NPD5327	Phase 3
0.6857	Remote Similarity	NPD3594	Approved
0.6857	Remote Similarity	NPD2605	Approved
0.6857	Remote Similarity	NPD3595	Approved
0.6857	Remote Similarity	NPD2606	Approved
0.6853	Remote Similarity	NPD5735	Approved
0.6849	Remote Similarity	NPD4725	Approved
0.6849	Remote Similarity	NPD4726	Approved
0.6849	Remote Similarity	NPD4721	Approved
0.6828	Remote Similarity	NPD7743	Approved
0.6828	Remote Similarity	NPD7742	Approved
0.6815	Remote Similarity	NPD3749	Approved
0.6815	Remote Similarity	NPD1751	Approved
0.6815	Remote Similarity	NPD5238	Clinical (unspecified phase)
0.6806	Remote Similarity	NPD2568	Approved
0.6806	Remote Similarity	NPD6353	Approved
0.68	Remote Similarity	NPD7213	Phase 3
0.68	Remote Similarity	NPD7212	Phase 2
0.6794	Remote Similarity	NPD5283	Phase 1
0.6792	Remote Similarity	NPD6959	Discontinued
0.6791	Remote Similarity	NPD2226	Clinical (unspecified phase)
0.6791	Remote Similarity	NPD5304	Approved
0.6791	Remote Similarity	NPD5303	Approved
0.6786	Remote Similarity	NPD3018	Phase 2
0.6783	Remote Similarity	NPD4140	Approved
0.6774	Remote Similarity	NPD37	Approved
0.6774	Remote Similarity	NPD3028	Approved
0.6772	Remote Similarity	NPD1444	Approved
0.6772	Remote Similarity	NPD1445	Approved
0.6755	Remote Similarity	NPD4160	Clinical (unspecified phase)
0.6752	Remote Similarity	NPD7768	Phase 2
0.6742	Remote Similarity	NPD497	Approved
0.6735	Remote Similarity	NPD5763	Approved
0.6735	Remote Similarity	NPD5762	Approved
0.6735	Remote Similarity	NPD2029	Clinical (unspecified phase)
0.6724	Remote Similarity	NPD111	Approved
0.6715	Remote Similarity	NPD422	Phase 1
0.6714	Remote Similarity	NPD6584	Phase 3
0.6713	Remote Similarity	NPD6407	Approved
0.6713	Remote Similarity	NPD6405	Approved
0.6712	Remote Similarity	NPD3748	Approved
0.6712	Remote Similarity	NPD1510	Phase 2
0.6712	Remote Similarity	NPD651	Clinical (unspecified phase)
0.6711	Remote Similarity	NPD7466	Approved
0.6692	Remote Similarity	NPD6671	Approved
0.6691	Remote Similarity	NPD4626	Approved
0.6691	Remote Similarity	NPD4589	Approved
0.6689	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6688	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD498	Approved
0.6667	Remote Similarity	NPD2238	Phase 2
0.6667	Remote Similarity	NPD496	Approved
0.6667	Remote Similarity	NPD3635	Approved
0.6667	Remote Similarity	NPD6234	Discontinued
0.6667	Remote Similarity	NPD3637	Approved
0.6667	Remote Similarity	NPD3636	Approved
0.6667	Remote Similarity	NPD495	Approved
0.6646	Remote Similarity	NPD4965	Approved
0.6646	Remote Similarity	NPD7229	Phase 3
0.6646	Remote Similarity	NPD6232	Discontinued
0.6646	Remote Similarity	NPD4966	Approved
0.6646	Remote Similarity	NPD4967	Phase 2
0.6645	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6644	Remote Similarity	NPD7718	Clinical (unspecified phase)
0.6644	Remote Similarity	NPD5698	Clinical (unspecified phase)
0.6644	Remote Similarity	NPD3638	Discontinued
0.6643	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6643	Remote Similarity	NPD2028	Clinical (unspecified phase)
0.6641	Remote Similarity	NPD6124	Clinical (unspecified phase)
0.6626	Remote Similarity	NPD7473	Discontinued
0.6619	Remote Similarity	NPD2983	Phase 2
0.6619	Remote Similarity	NPD2982	Phase 2
0.6619	Remote Similarity	NPD4659	Approved
0.6615	Remote Similarity	NPD5451	Approved
0.6609	Remote Similarity	NPD9089	Approved
0.66	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.66	Remote Similarity	NPD7003	Approved
0.6596	Remote Similarity	NPD2195	Approved
0.6596	Remote Similarity	NPD2194	Approved
0.6594	Remote Similarity	NPD5350	Clinical (unspecified phase)
0.6594	Remote Similarity	NPD5351	Clinical (unspecified phase)
0.6575	Remote Similarity	NPD2157	Approved
0.6571	Remote Similarity	NPD6696	Suspended
0.6567	Remote Similarity	NPD709	Approved
0.6556	Remote Similarity	NPD8131	Suspended
0.6556	Remote Similarity	NPD7910	Clinical (unspecified phase)
0.6554	Remote Similarity	NPD1632	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD1555	Discontinued
0.6552	Remote Similarity	NPD1240	Approved
0.6547	Remote Similarity	NPD2232	Approved
0.6547	Remote Similarity	NPD2233	Approved
0.6547	Remote Similarity	NPD2981	Phase 2
0.6547	Remote Similarity	NPD2230	Approved
0.6541	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6541	Remote Similarity	NPD7159	Clinical (unspecified phase)
0.6536	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6528	Remote Similarity	NPD6812	Clinical (unspecified phase)
0.6525	Remote Similarity	NPD4104	Clinical (unspecified phase)
0.6525	Remote Similarity	NPD4103	Phase 2
0.6525	Remote Similarity	NPD1164	Approved
0.6525	Remote Similarity	NPD2797	Approved
0.6522	Remote Similarity	NPD9093	Approved
0.6519	Remote Similarity	NPD7819	Suspended
0.6519	Remote Similarity	NPD405	Clinical (unspecified phase)
0.651	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.651	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6509	Remote Similarity	NPD8053	Approved
0.6509	Remote Similarity	NPD8054	Approved
0.6507	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6507	Remote Similarity	NPD5124	Phase 1
0.65	Remote Similarity	NPD6582	Phase 2
0.65	Remote Similarity	NPD6583	Phase 3

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