NPASS Compound

Structure

CID149337 OpenBabel06191715522D 22 24 0 0 0 0 0 0 0 0999 V2000 4.3301 -2.5000 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 -2.5981 0.5000 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 2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 2.0000 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 1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 0.5000 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 3.4641 -1.0000 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 -0.8660 1.5000 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 -0.8660 0.5000 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 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 19 1 0 0 0 0 2 20 1 0 0 0 0 3 21 1 0 0 0 0 4 22 1 0 0 0 0 5 6 2 0 0 0 0 5 11 1 0 0 0 0 6 12 1 0 0 0 0 7 8 1 0 0 0 0 7 13 2 0 0 0 0 8 14 2 0 0 0 0 9 11 2 0 0 0 0 9 13 1 0 0 0 0 10 12 2 0 0 0 0 10 15 1 0 0 0 0 11 14 1 0 0 0 0 12 16 1 0 0 0 0 13 19 1 0 0 0 0 14 16 1 0 0 0 0 15 17 2 0 0 0 0 15 20 1 0 0 0 0 16 18 2 0 0 0 0 17 18 1 0 0 0 0 17 21 1 0 0 0 0 18 22 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	298.12
Volume:	310.921
LogP:	3.903
LogD:	3.551
LogS:	-5.236
# Rotatable Bonds:	4
TPSA:	36.92
# H-Bond Aceptor:	4
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.682
Synthetic Accessibility Score:	2.012
Fsp3:	0.222
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:	-4.683
MDCK Permeability:	5.0827587983803824e-05
Pgp-inhibitor:	0.561
Pgp-substrate:	0.01
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.008
30% Bioavailability (F30%):	0.139

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.126
Plasma Protein Binding (PPB):	85.63420867919922%
Volume Distribution (VD):	0.524
Pgp-substrate:	9.376008987426758%

ADMET: Metabolism

CYP1A2-inhibitor:	0.941
CYP1A2-substrate:	0.98
CYP2C19-inhibitor:	0.849
CYP2C19-substrate:	0.889
CYP2C9-inhibitor:	0.469
CYP2C9-substrate:	0.933
CYP2D6-inhibitor:	0.233
CYP2D6-substrate:	0.944
CYP3A4-inhibitor:	0.62
CYP3A4-substrate:	0.618

ADMET: Excretion

Clearance (CL):	8.876
Half-life (T1/2):	0.308

ADMET: Toxicity

hERG Blockers:	0.351
Human Hepatotoxicity (H-HT):	0.087
Drug-inuced Liver Injury (DILI):	0.915
AMES Toxicity:	0.639
Rat Oral Acute Toxicity:	0.112
Maximum Recommended Daily Dose:	0.265
Skin Sensitization:	0.945
Carcinogencity:	0.383
Eye Corrosion:	0.021
Eye Irritation:	0.856
Respiratory Toxicity:	0.249

Download Data

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

Natural Product: NPC149337

Natural Product ID:	NPC149337
*Common Name:**	2,3,4,7-Tetramethoxyphenanthrene
IUPAC Name:	2,3,4,7-tetramethoxyphenanthrene
Synonyms:	2,3,4,7-Tetramethoxy-Phenanthrene
Standard InCHIKey:	SZWNNHPMXYWRRE-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C18H18O4/c1-19-13-7-8-14-11(9-13)5-6-12-10-15(20-2)17(21-3)18(22-4)16(12)14/h5-10H,1-4H3
SMILES:	COc1ccc2c(c1)ccc1c2c(OC)c(c(c1)OC)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL73252
PubChem CID:	11437978
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000025] Phenanthrenes and derivatives

*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
NPO3894	Dendrobium nobile	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11575955]
NPO3987	Syzygium aromaticum	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[1402962]
NPO11479	Sargassum siliquastrum	Species	Sargassaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15921416]
NPO3894	Dendrobium nobile	Species	Orchidaceae	Eukaryota	stems	Yunnan Province, China	2004	PMID[17253844]
NPO3894	Dendrobium nobile	Species	Orchidaceae	Eukaryota	Stems	purchased from Kyoungdong Oriental Herbal Market, Seoul, Korea	2006-APR	PMID[18052323]
NPO11479	Sargassum siliquastrum	Species	Sargassaceae	Eukaryota	n.a.	subtidal zone (0-2 m) off the southwestern shore of Jeju Island, Korea	2003-Apr	PMID[18817444]
NPO11479	Sargassum siliquastrum	Species	Sargassaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19006667]
NPO2188	Dendrobium candidum	Species	Orchidaceae	Eukaryota	n.a.	stem	n.a.	PMID[19182417]
NPO11479	Sargassum siliquastrum	Species	Sargassaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21377877]
NPO23332	Dendrobium fimbriatum	Species	Orchidaceae	Eukaryota	stems	n.a.	n.a.	PMID[25316316]
NPO3987	Syzygium aromaticum	Species	Myrtaceae	Eukaryota	Flower Buds	n.a.	n.a.	PMID[26977531]
NPO3894	Dendrobium nobile	Species	Orchidaceae	Eukaryota	Stems	n.a.	n.a.	PMID[27310249]
NPO11479	Sargassum siliquastrum	Species	Sargassaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[28720331]
NPO865	Dendrobium loddigesii	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31291099]
NPO3987	Syzygium aromaticum	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8904847]
NPO3987	Syzygium aromaticum	Species	Myrtaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO3987	Syzygium aromaticum	Species	Myrtaceae	Eukaryota	Bark	n.a.	n.a.	Database[FooDB]
NPO3987	Syzygium aromaticum	Species	Myrtaceae	Eukaryota	Essential Oil	n.a.	n.a.	Database[FooDB]
NPO3987	Syzygium aromaticum	Species	Myrtaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO3987	Syzygium aromaticum	Species	Myrtaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO3987	Syzygium aromaticum	Species	Myrtaceae	Eukaryota	Stem	n.a.	n.a.	Database[FooDB]
NPO3987	Syzygium aromaticum	Species	Myrtaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO3987	Syzygium aromaticum	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO865	Dendrobium loddigesii	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO20900	Dendrobium chrysotoxum	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO3894	Dendrobium nobile	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11889	Dendrobium chrysanthum	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3894	Dendrobium nobile	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3987	Syzygium aromaticum	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO865	Dendrobium loddigesii	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20900	Dendrobium chrysotoxum	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO865	Dendrobium loddigesii	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO3987	Syzygium aromaticum	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO3894	Dendrobium nobile	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO3894	Dendrobium nobile	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO11889	Dendrobium chrysanthum	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO23332	Dendrobium fimbriatum	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO2188	Dendrobium candidum	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO865	Dendrobium loddigesii	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO20900	Dendrobium chrysotoxum	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO3987	Syzygium aromaticum	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO865	Dendrobium loddigesii	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15591	Tolpis webbii	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3987	Syzygium aromaticum	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3894	Dendrobium nobile	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2188	Dendrobium candidum	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23332	Dendrobium fimbriatum	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20900	Dendrobium chrysotoxum	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11889	Dendrobium chrysanthum	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8787	Ariocarpus scapharostrus	Species	Cactaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11479	Sargassum siliquastrum	Species	Sargassaceae	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	5
IC50	1

Activity Type	# Activity
Cell Line	5
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	ED50	>	25.0	uM	PMID[534072]
NPT83	Cell Line	MCF7	Homo sapiens	ED50	>	25.0	uM	PMID[534072]
NPT139	Cell Line	HT-29	Homo sapiens	ED50	>	25.0	uM	PMID[534072]
NPT373	Cell Line	SK-MEL-5	Homo sapiens	ED50	>	25.0	uM	PMID[534072]
NPT3958	Cell Line	MLM		ED50	>	25.0	uM	PMID[534072]
NPT875	Organism	Bos taurus	Bos taurus	IC50	>	40000.0	nM	PMID[534072]

☑ 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 NPC149337 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	608
0.1-0.2	2105
0.2-0.3	6265
0.3-0.4	12678
0.4-0.5	3780
0.5-0.6	4682
0.6-0.7	8207
0.7-0.8	3661
0.8-0.85	498
0.85-0.9	177
0.9-0.95	34
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC471983
0.9677	High Similarity	NPC471986
0.9538	High Similarity	NPC266006
0.9466	High Similarity	NPC132804
0.9466	High Similarity	NPC275061
0.9466	High Similarity	NPC220344
0.9466	High Similarity	NPC243996
0.9394	High Similarity	NPC308768
0.9394	High Similarity	NPC12668
0.9389	High Similarity	NPC200935
0.9389	High Similarity	NPC242715
0.9389	High Similarity	NPC230919
0.9389	High Similarity	NPC22902
0.9389	High Similarity	NPC56329
0.9389	High Similarity	NPC266453
0.9318	High Similarity	NPC105847
0.9318	High Similarity	NPC218131
0.9318	High Similarity	NPC243759
0.9313	High Similarity	NPC30632
0.9254	High Similarity	NPC175838
0.9254	High Similarity	NPC183709
0.9242	High Similarity	NPC151656
0.9237	High Similarity	NPC108198
0.9237	High Similarity	NPC69029
0.9237	High Similarity	NPC158142
0.9237	High Similarity	NPC200557
0.9237	High Similarity	NPC10314
0.9237	High Similarity	NPC294884
0.9237	High Similarity	NPC241241
0.9167	High Similarity	NPC205442
0.9167	High Similarity	NPC202846
0.9167	High Similarity	NPC143139
0.916	High Similarity	NPC125649
0.9104	High Similarity	NPC295719
0.9104	High Similarity	NPC165026
0.9104	High Similarity	NPC34431
0.9104	High Similarity	NPC73505
0.9091	High Similarity	NPC111655
0.9091	High Similarity	NPC313081
0.903	High Similarity	NPC212942
0.903	High Similarity	NPC29868
0.903	High Similarity	NPC79622
0.9015	High Similarity	NPC160697
0.9008	High Similarity	NPC228843
0.8992	High Similarity	NPC149008
0.8992	High Similarity	NPC283114
0.8992	High Similarity	NPC215300
0.8992	High Similarity	NPC207702
0.8955	High Similarity	NPC272157
0.8955	High Similarity	NPC6262
0.8955	High Similarity	NPC196420
0.8955	High Similarity	NPC201145
0.8955	High Similarity	NPC73535
0.8955	High Similarity	NPC25111
0.8955	High Similarity	NPC90615
0.8952	High Similarity	NPC475961
0.8952	High Similarity	NPC15805
0.8952	High Similarity	NPC254625
0.8931	High Similarity	NPC282508
0.8923	High Similarity	NPC474227
0.8915	High Similarity	NPC53781
0.8897	High Similarity	NPC472089
0.8889	High Similarity	NPC184613
0.8889	High Similarity	NPC477886
0.8881	High Similarity	NPC476639
0.8881	High Similarity	NPC300846
0.8881	High Similarity	NPC114155
0.8872	High Similarity	NPC209199
0.8864	High Similarity	NPC161958
0.8864	High Similarity	NPC14224
0.8855	High Similarity	NPC126836
0.8849	High Similarity	NPC126291
0.8846	High Similarity	NPC38017
0.8837	High Similarity	NPC170485
0.8837	High Similarity	NPC223953
0.8837	High Similarity	NPC244364
0.8832	High Similarity	NPC472087
0.8832	High Similarity	NPC472088
0.8806	High Similarity	NPC37410
0.8806	High Similarity	NPC283009
0.8806	High Similarity	NPC261873
0.8797	High Similarity	NPC32778
0.8788	High Similarity	NPC184928
0.8788	High Similarity	NPC15543
0.8788	High Similarity	NPC474238
0.8788	High Similarity	NPC141493
0.8786	High Similarity	NPC262297
0.876	High Similarity	NPC105925
0.876	High Similarity	NPC105031
0.876	High Similarity	NPC113495
0.875	High Similarity	NPC114171
0.875	High Similarity	NPC6300
0.875	High Similarity	NPC230124
0.8741	High Similarity	NPC191462
0.8741	High Similarity	NPC472648
0.8741	High Similarity	NPC170328
0.8741	High Similarity	NPC472649
0.8741	High Similarity	NPC206525
0.8741	High Similarity	NPC133463
0.8741	High Similarity	NPC472647
0.8731	High Similarity	NPC103967
0.8722	High Similarity	NPC475856
0.8722	High Similarity	NPC102256
0.8712	High Similarity	NPC254000
0.871	High Similarity	NPC123948
0.8705	High Similarity	NPC469795
0.8702	High Similarity	NPC154866
0.8702	High Similarity	NPC31707
0.8702	High Similarity	NPC28765
0.8696	High Similarity	NPC470917
0.8686	High Similarity	NPC472092
0.8686	High Similarity	NPC472090
0.8686	High Similarity	NPC472091
0.8682	High Similarity	NPC228503
0.8682	High Similarity	NPC138248
0.8676	High Similarity	NPC71465
0.8676	High Similarity	NPC472646
0.8671	High Similarity	NPC114124
0.8667	High Similarity	NPC258780
0.8667	High Similarity	NPC256262
0.8661	High Similarity	NPC472596
0.864	High Similarity	NPC25648
0.8636	High Similarity	NPC469951
0.8636	High Similarity	NPC469963
0.8633	High Similarity	NPC469630
0.8633	High Similarity	NPC258083
0.8626	High Similarity	NPC202904
0.8626	High Similarity	NPC236760
0.8626	High Similarity	NPC266555
0.8626	High Similarity	NPC124452
0.8626	High Similarity	NPC293054
0.8626	High Similarity	NPC324112
0.8626	High Similarity	NPC100129
0.8626	High Similarity	NPC169474
0.8626	High Similarity	NPC252131
0.8626	High Similarity	NPC473221
0.8626	High Similarity	NPC246620
0.8626	High Similarity	NPC242032
0.8626	High Similarity	NPC82679
0.8626	High Similarity	NPC189248
0.8626	High Similarity	NPC236791
0.8626	High Similarity	NPC159968
0.8626	High Similarity	NPC74817
0.8626	High Similarity	NPC282000
0.8623	High Similarity	NPC265075
0.8615	High Similarity	NPC105718
0.8615	High Similarity	NPC278955
0.8613	High Similarity	NPC55947
0.8605	High Similarity	NPC282496
0.8605	High Similarity	NPC233526
0.8603	High Similarity	NPC78047
0.8593	High Similarity	NPC469659
0.8593	High Similarity	NPC7515
0.8593	High Similarity	NPC276026
0.8593	High Similarity	NPC188378
0.8593	High Similarity	NPC555
0.8593	High Similarity	NPC206737
0.8593	High Similarity	NPC56764
0.8593	High Similarity	NPC289258
0.8593	High Similarity	NPC145722
0.8593	High Similarity	NPC185680
0.8593	High Similarity	NPC256776
0.8582	High Similarity	NPC233980
0.8582	High Similarity	NPC218884
0.8571	High Similarity	NPC224157
0.8571	High Similarity	NPC192687
0.8561	High Similarity	NPC191231
0.8561	High Similarity	NPC23012
0.8551	High Similarity	NPC273623
0.855	High Similarity	NPC214406
0.855	High Similarity	NPC18924
0.855	High Similarity	NPC112571
0.855	High Similarity	NPC44748
0.855	High Similarity	NPC103823
0.855	High Similarity	NPC28730
0.855	High Similarity	NPC223136
0.855	High Similarity	NPC285725
0.855	High Similarity	NPC50683
0.855	High Similarity	NPC82299
0.855	High Similarity	NPC78974
0.854	High Similarity	NPC35550
0.8529	High Similarity	NPC55239
0.8529	High Similarity	NPC214853
0.8529	High Similarity	NPC240279
0.8529	High Similarity	NPC180602
0.8527	High Similarity	NPC261661
0.8521	High Similarity	NPC474397
0.8519	High Similarity	NPC469610
0.8511	High Similarity	NPC221318
0.8507	High Similarity	NPC8899
0.8504	High Similarity	NPC308217
0.8496	Intermediate Similarity	NPC190144
0.8496	Intermediate Similarity	NPC471518
0.8496	Intermediate Similarity	NPC471519
0.8489	Intermediate Similarity	NPC71046
0.8485	Intermediate Similarity	NPC21563
0.8485	Intermediate Similarity	NPC127587
0.8478	Intermediate Similarity	NPC260741
0.8478	Intermediate Similarity	NPC70682
0.8478	Intermediate Similarity	NPC32630

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 NPC149337 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	520
0.1-0.2	986
0.2-0.3	1673
0.3-0.4	2812
0.4-0.5	1626
0.5-0.6	902
0.6-0.7	533
0.7-0.8	90
0.8-0.85	8
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8358	Intermediate Similarity	NPD4625	Phase 3
0.8346	Intermediate Similarity	NPD3018	Phase 2
0.832	Intermediate Similarity	NPD5283	Phase 1
0.8244	Intermediate Similarity	NPD2981	Phase 2
0.8222	Intermediate Similarity	NPD3027	Phase 3
0.8182	Intermediate Similarity	NPD2982	Phase 2
0.8182	Intermediate Similarity	NPD2983	Phase 2
0.8162	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.8105	Intermediate Similarity	NPD6232	Discontinued
0.8015	Intermediate Similarity	NPD4908	Phase 1
0.8015	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7949	Intermediate Similarity	NPD7473	Discontinued
0.7941	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7914	Intermediate Similarity	NPD1613	Approved
0.7914	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7848	Intermediate Similarity	NPD5844	Phase 1
0.7815	Intermediate Similarity	NPD37	Approved
0.7803	Intermediate Similarity	NPD1651	Approved
0.7762	Intermediate Similarity	NPD3539	Phase 1
0.7761	Intermediate Similarity	NPD3705	Approved
0.7737	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7724	Intermediate Similarity	NPD6674	Discontinued
0.7724	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7708	Intermediate Similarity	NPD3540	Phase 1
0.7669	Intermediate Similarity	NPD5691	Approved
0.7662	Intermediate Similarity	NPD4966	Approved
0.7662	Intermediate Similarity	NPD4967	Phase 2
0.7662	Intermediate Similarity	NPD4965	Approved
0.7651	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD4749	Approved
0.7647	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.763	Intermediate Similarity	NPD1610	Phase 2
0.7619	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7612	Intermediate Similarity	NPD4626	Approved
0.7606	Intermediate Similarity	NPD3657	Discovery
0.76	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.758	Intermediate Similarity	NPD7199	Phase 2
0.7568	Intermediate Similarity	NPD7124	Phase 2
0.7564	Intermediate Similarity	NPD6234	Discontinued
0.7552	Intermediate Similarity	NPD4097	Suspended
0.7535	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7535	Intermediate Similarity	NPD3620	Phase 2
0.7519	Intermediate Similarity	NPD5536	Phase 2
0.7518	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7518	Intermediate Similarity	NPD5109	Approved
0.7518	Intermediate Similarity	NPD5110	Phase 2
0.7518	Intermediate Similarity	NPD5111	Phase 2
0.75	Intermediate Similarity	NPD1611	Approved
0.75	Intermediate Similarity	NPD1281	Approved
0.75	Intermediate Similarity	NPD4055	Discovery
0.75	Intermediate Similarity	NPD4005	Discontinued
0.7484	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7463	Intermediate Similarity	NPD1548	Phase 1
0.7442	Intermediate Similarity	NPD5451	Approved
0.7417	Intermediate Similarity	NPD5261	Clinical (unspecified phase)
0.7413	Intermediate Similarity	NPD4060	Phase 1
0.7405	Intermediate Similarity	NPD5494	Approved
0.7397	Intermediate Similarity	NPD2438	Suspended
0.7394	Intermediate Similarity	NPD6812	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD5327	Phase 3
0.7386	Intermediate Similarity	NPD7261	Clinical (unspecified phase)
0.7379	Intermediate Similarity	NPD6111	Discontinued
0.7346	Intermediate Similarity	NPD8252	Approved
0.7346	Intermediate Similarity	NPD8099	Discontinued
0.7346	Intermediate Similarity	NPD8251	Approved
0.7338	Intermediate Similarity	NPD8651	Approved
0.7338	Intermediate Similarity	NPD1283	Approved
0.7328	Intermediate Similarity	NPD228	Approved
0.7325	Intermediate Similarity	NPD6788	Approved
0.7308	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7301	Intermediate Similarity	NPD8156	Discontinued
0.7292	Intermediate Similarity	NPD2979	Phase 3
0.7287	Intermediate Similarity	NPD2342	Discontinued
0.7267	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.7266	Intermediate Similarity	NPD1669	Approved
0.725	Intermediate Similarity	NPD6959	Discontinued
0.7244	Intermediate Similarity	NPD1934	Approved
0.7239	Intermediate Similarity	NPD7228	Approved
0.7234	Intermediate Similarity	NPD4624	Approved
0.7214	Intermediate Similarity	NPD2922	Phase 1
0.7211	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7211	Intermediate Similarity	NPD3748	Approved
0.7211	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7205	Intermediate Similarity	NPD7229	Phase 3
0.72	Intermediate Similarity	NPD7466	Approved
0.7197	Intermediate Similarity	NPD2801	Approved
0.7197	Intermediate Similarity	NPD7819	Suspended
0.7183	Intermediate Similarity	NPD2861	Phase 2
0.7181	Intermediate Similarity	NPD4664	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD5089	Approved
0.7179	Intermediate Similarity	NPD5090	Approved
0.7176	Intermediate Similarity	NPD4750	Phase 3
0.7171	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7162	Intermediate Similarity	NPD6100	Approved
0.7162	Intermediate Similarity	NPD6099	Approved
0.716	Intermediate Similarity	NPD3926	Phase 2
0.7153	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD3817	Phase 2
0.7143	Intermediate Similarity	NPD5535	Approved
0.7143	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7124	Intermediate Similarity	NPD4584	Approved
0.7123	Intermediate Similarity	NPD5735	Approved
0.7117	Intermediate Similarity	NPD6166	Phase 2
0.7117	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7117	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7111	Intermediate Similarity	NPD709	Approved
0.7108	Intermediate Similarity	NPD6996	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD4108	Discontinued
0.7092	Intermediate Similarity	NPD6696	Suspended
0.7089	Intermediate Similarity	NPD4585	Approved
0.7086	Intermediate Similarity	NPD6658	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD7003	Approved
0.7086	Intermediate Similarity	NPD3892	Phase 2
0.7066	Intermediate Similarity	NPD7240	Approved
0.7063	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD7040	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD4357	Discontinued
0.7059	Intermediate Similarity	NPD7041	Phase 2
0.7051	Intermediate Similarity	NPD6055	Clinical (unspecified phase)
0.7047	Intermediate Similarity	NPD2531	Phase 2
0.7047	Intermediate Similarity	NPD2796	Approved
0.7045	Intermediate Similarity	NPD3021	Approved
0.7045	Intermediate Similarity	NPD3022	Approved
0.7041	Intermediate Similarity	NPD8053	Approved
0.7041	Intermediate Similarity	NPD8054	Approved
0.7034	Intermediate Similarity	NPD5718	Phase 2
0.7027	Intermediate Similarity	NPD6895	Approved
0.7027	Intermediate Similarity	NPD6896	Approved
0.7019	Intermediate Similarity	NPD919	Approved
0.7015	Intermediate Similarity	NPD7635	Approved
0.7014	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7013	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7013	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7013	Intermediate Similarity	NPD7447	Phase 1
0.7	Intermediate Similarity	NPD7768	Phase 2
0.7	Intermediate Similarity	NPD5762	Approved
0.7	Intermediate Similarity	NPD4581	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD5763	Approved
0.7	Intermediate Similarity	NPD3882	Suspended
0.6985	Remote Similarity	NPD7157	Approved
0.6985	Remote Similarity	NPD6387	Discontinued
0.6981	Remote Similarity	NPD1465	Phase 2
0.6978	Remote Similarity	NPD6516	Phase 2
0.6978	Remote Similarity	NPD5846	Approved
0.6974	Remote Similarity	NPD6331	Phase 2
0.6974	Remote Similarity	NPD3750	Approved
0.6974	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.697	Remote Similarity	NPD2684	Approved
0.6966	Remote Similarity	NPD7095	Approved
0.6963	Remote Similarity	NPD498	Approved
0.6963	Remote Similarity	NPD495	Approved
0.6963	Remote Similarity	NPD496	Approved
0.6959	Remote Similarity	NPD4579	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD1607	Approved
0.6954	Remote Similarity	NPD2808	Discontinued
0.6948	Remote Similarity	NPD7213	Phase 3
0.6948	Remote Similarity	NPD7212	Phase 2
0.6948	Remote Similarity	NPD7390	Discontinued
0.6948	Remote Similarity	NPD1511	Approved
0.6943	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6939	Remote Similarity	NPD4140	Approved
0.6937	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD1247	Approved
0.6928	Remote Similarity	NPD5241	Discontinued
0.6923	Remote Similarity	NPD7549	Discontinued
0.6918	Remote Similarity	NPD6798	Discontinued
0.6918	Remote Similarity	NPD7294	Phase 1
0.6913	Remote Similarity	NPD4537	Clinical (unspecified phase)
0.6913	Remote Similarity	NPD4536	Approved
0.6913	Remote Similarity	NPD4538	Approved
0.6912	Remote Similarity	NPD497	Approved
0.6908	Remote Similarity	NPD5177	Phase 3
0.6906	Remote Similarity	NPD3445	Approved
0.6906	Remote Similarity	NPD3444	Approved
0.6906	Remote Similarity	NPD3443	Approved
0.6903	Remote Similarity	NPD2532	Approved
0.6903	Remote Similarity	NPD2534	Approved
0.6903	Remote Similarity	NPD2533	Approved
0.6903	Remote Similarity	NPD1424	Approved
0.6903	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6903	Remote Similarity	NPD7446	Clinical (unspecified phase)
0.6899	Remote Similarity	NPD6599	Discontinued
0.6899	Remote Similarity	NPD4678	Approved
0.6899	Remote Similarity	NPD940	Approved
0.6899	Remote Similarity	NPD4675	Approved
0.6899	Remote Similarity	NPD846	Approved
0.6899	Remote Similarity	NPD4380	Phase 2
0.6892	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6892	Remote Similarity	NPD5124	Phase 1
0.689	Remote Similarity	NPD3051	Approved
0.6889	Remote Similarity	NPD7843	Approved
0.6887	Remote Similarity	NPD2029	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD1653	Approved
0.6879	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD422	Phase 1
0.6875	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD6584	Phase 3
0.6871	Remote Similarity	NPD4474	Approved
0.6871	Remote Similarity	NPD8032	Phase 2

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data