NPASS Compound

Structure

NPC144257 OpenBabel07101719192D 50 54 0 0 1 0 0 0 0 0999 V2000 -0.0976 -4.5607 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4562 -5.1705 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8274 -1.2460 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9928 -2.6916 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3310 0.6769 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9758 1.3931 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4752 4.2872 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6406 3.8053 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5785 0.2343 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4778 -0.7241 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3578 -1.1160 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9549 -2.8725 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0049 -2.7108 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5700 -2.1306 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6065 -2.7666 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2074 -3.5200 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6699 -1.8072 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2350 -1.2270 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1582 -1.2460 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1582 -0.2823 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3107 -0.9724 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3383 -0.9637 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3791 0.9403 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0349 2.3882 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6082 1.5573 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8553 -4.4171 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9928 -1.7279 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2850 -1.0653 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3236 0.1995 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6692 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2163 0.6769 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.1729 -0.4818 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.9934 2.4889 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.9500 -0.1617 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8346 -0.4818 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6692 0.9637 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.9637 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2736 0.4766 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4752 3.3235 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6981 -0.1577 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7098 -0.2190 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8346 1.4455 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.0418 2.3369 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5651 0.5802 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8346 -1.4455 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8346 1.4455 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4389 3.3235 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.3853 1.6085 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.0533 -0.8738 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 26 1 0 0 0 0 2 26 1 0 0 0 0 3 27 1 0 0 0 0 4 27 1 0 0 0 0 5 38 1 0 0 0 0 6 38 1 0 0 0 0 7 39 1 0 0 0 0 8 39 1 0 0 0 0 9 40 1 0 0 0 0 10 40 1 0 0 0 0 11 41 1 0 0 0 0 12 13 2 0 0 0 0 12 14 1 0 0 0 0 13 17 1 0 0 0 0 14 18 2 0 0 0 0 15 16 1 0 0 0 0 15 21 1 0 0 0 0 16 26 2 0 0 0 0 17 28 2 0 0 0 0 18 28 1 0 0 0 0 19 20 1 0 0 0 0 19 27 2 0 0 0 0 20 29 1 0 0 0 0 21 41 1 0 0 0 0 22 30 1 0 0 0 0 23 29 1 0 0 0 0 24 33 1 0 0 0 0 24 42 1 0 0 0 0 25 44 1 0 0 0 0 28 34 1 0 0 0 0 29 41 1 6 0 0 0 30 35 1 0 0 0 0 30 36 2 0 0 0 0 31 25 1 6 0 0 0 31 38 1 0 0 0 0 31 40 1 0 0 0 0 32 22 1 1 0 0 0 32 38 1 0 0 0 0 32 50 1 0 0 0 0 33 39 1 1 0 0 0 33 49 1 0 0 0 0 34 45 2 0 0 0 0 35 43 1 0 0 0 0 35 46 2 0 0 0 0 36 42 1 0 0 0 0 36 49 1 0 0 0 0 37 42 1 0 0 0 0 37 43 1 0 0 0 0 37 47 2 0 0 0 0 39 48 1 0 0 0 0 40 50 1 0 0 0 0 41 43 1 1 0 0 0 42 23 1 6 0 0 0 43 34 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	688.43
Volume:	747.305
LogP:	8.237
LogD:	5.478
LogS:	-5.488
# Rotatable Bonds:	11
TPSA:	110.13
# H-Bond Aceptor:	7
# H-Bond Donor:	2
# Rings:	5
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.137
Synthetic Accessibility Score:	6.765
Fsp3:	0.651
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.004
MDCK Permeability:	1.9978784621343948e-05
Pgp-inhibitor:	0.635
Pgp-substrate:	0.748
Human Intestinal Absorption (HIA):	0.023
20% Bioavailability (F20%):	0.6
30% Bioavailability (F30%):	0.956

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.897
Plasma Protein Binding (PPB):	83.99678802490234%
Volume Distribution (VD):	1.766
Pgp-substrate:	8.783517837524414%

ADMET: Metabolism

CYP1A2-inhibitor:	0.004
CYP1A2-substrate:	0.123
CYP2C19-inhibitor:	0.113
CYP2C19-substrate:	0.872
CYP2C9-inhibitor:	0.447
CYP2C9-substrate:	0.067
CYP2D6-inhibitor:	0.037
CYP2D6-substrate:	0.013
CYP3A4-inhibitor:	0.885
CYP3A4-substrate:	0.915

ADMET: Excretion

Clearance (CL):	10.844
Half-life (T1/2):	0.009

ADMET: Toxicity

hERG Blockers:	0.005
Human Hepatotoxicity (H-HT):	0.894
Drug-inuced Liver Injury (DILI):	0.612
AMES Toxicity:	0.008
Rat Oral Acute Toxicity:	0.663
Maximum Recommended Daily Dose:	0.963
Skin Sensitization:	0.661
Carcinogencity:	0.274
Eye Corrosion:	0.003
Eye Irritation:	0.019
Respiratory Toxicity:	0.985

Download Data

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

Natural Product: NPC144257

Natural Product ID:	NPC144257
*Common Name:**	MDPGYGAHTYWVFB-QESWIGJASA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	MDPGYGAHTYWVFB-QESWIGJASA-N
Standard InCHI:	InChI=1S/C43H60O7/c1-26(2)16-15-21-41(11)29(20-19-27(3)4)23-42-24-33(39(7,8)48)49-36(42)30(22-32-38(5,6)31(25-44)40(9,10)50-32)35(46)43(41,37(42)47)34(45)28-17-13-12-14-18-28/h12-14,16-19,29,31-33,44,48H,15,20-25H2,1-11H3/t29-,31-,32-,33-,41+,42-,43-/m0/s1
SMILES:	CC(=CCC[C@]1(C)[C@@H](CC=C(C)C)C[C@]23C[C@@H](C(C)(C)O)OC2=C(C[C@H]2C(C)(C)[C@H](CO)C(C)(C)O2)C(=O)[C@@]1(C(=O)c1ccccc1)C3=O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2419285
PubChem CID:	73355235
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0002049] Terpene glycosides

*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
NPO33449	hypericum cohaerens	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23957453]

☑ 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
IC50	5

Activity Type	# Activity
Cell Line	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT660	Cell Line	SW480	Homo sapiens	IC50	=	9200.0	nM	PMID[481447]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	>	20000.0	nM	PMID[481447]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	17900.0	nM	PMID[481447]
NPT659	Cell Line	SMMC-7721	Homo sapiens	IC50	=	8200.0	nM	PMID[481447]
NPT116	Cell Line	HL-60	Homo sapiens	IC50	=	12600.0	nM	PMID[481447]

☑ 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 NPC144257 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	283
0.1-0.2	916
0.2-0.3	2201
0.3-0.4	4915
0.4-0.5	10565
0.5-0.6	15944
0.6-0.7	7062
0.7-0.8	778
0.8-0.85	7
0.85-0.9	20
0.9-0.95	5
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.952	High Similarity	NPC146239
0.9286	High Similarity	NPC328997
0.9286	High Similarity	NPC294050
0.9141	High Similarity	NPC316553
0.9077	High Similarity	NPC471334
0.8828	High Similarity	NPC325740
0.872	High Similarity	NPC61651
0.8333	Intermediate Similarity	NPC478108
0.8308	Intermediate Similarity	NPC476234
0.8268	Intermediate Similarity	NPC260886
0.824	Intermediate Similarity	NPC218855
0.814	Intermediate Similarity	NPC268930
0.811	Intermediate Similarity	NPC130591
0.811	Intermediate Similarity	NPC234637
0.8074	Intermediate Similarity	NPC81135
0.806	Intermediate Similarity	NPC472694
0.806	Intermediate Similarity	NPC472693
0.8043	Intermediate Similarity	NPC209851
0.8041	Intermediate Similarity	NPC472548
0.8031	Intermediate Similarity	NPC471481
0.8029	Intermediate Similarity	NPC262819
0.8	Intermediate Similarity	NPC301946
0.8	Intermediate Similarity	NPC277053
0.7985	Intermediate Similarity	NPC472681
0.7973	Intermediate Similarity	NPC471103
0.7973	Intermediate Similarity	NPC306799
0.7973	Intermediate Similarity	NPC101043
0.7973	Intermediate Similarity	NPC51602
0.7971	Intermediate Similarity	NPC472682
0.7971	Intermediate Similarity	NPC472692
0.7959	Intermediate Similarity	NPC273798
0.7955	Intermediate Similarity	NPC105709
0.7933	Intermediate Similarity	NPC473670
0.7933	Intermediate Similarity	NPC472549
0.7933	Intermediate Similarity	NPC21410
0.7931	Intermediate Similarity	NPC471912
0.7931	Intermediate Similarity	NPC80895
0.7919	Intermediate Similarity	NPC477905
0.7917	Intermediate Similarity	NPC63737
0.7905	Intermediate Similarity	NPC91730
0.7905	Intermediate Similarity	NPC7095
0.7899	Intermediate Similarity	NPC473443
0.7881	Intermediate Similarity	NPC106895
0.7877	Intermediate Similarity	NPC127857
0.7852	Intermediate Similarity	NPC328107
0.7852	Intermediate Similarity	NPC197037
0.7852	Intermediate Similarity	NPC132810
0.7838	Intermediate Similarity	NPC60509
0.7838	Intermediate Similarity	NPC81698
0.7838	Intermediate Similarity	NPC250046
0.7826	Intermediate Similarity	NPC225103
0.782	Intermediate Similarity	NPC476225
0.7815	Intermediate Similarity	NPC282239
0.7786	Intermediate Similarity	NPC80599
0.7785	Intermediate Similarity	NPC198455
0.7785	Intermediate Similarity	NPC112216
0.7785	Intermediate Similarity	NPC165260
0.7785	Intermediate Similarity	NPC161239
0.7778	Intermediate Similarity	NPC472547
0.7778	Intermediate Similarity	NPC473440
0.7778	Intermediate Similarity	NPC275592
0.7778	Intermediate Similarity	NPC100913
0.7778	Intermediate Similarity	NPC65627
0.777	Intermediate Similarity	NPC217918
0.777	Intermediate Similarity	NPC471832
0.777	Intermediate Similarity	NPC472388
0.7763	Intermediate Similarity	NPC217091
0.7762	Intermediate Similarity	NPC39549
0.776	Intermediate Similarity	NPC471332
0.776	Intermediate Similarity	NPC471333
0.7754	Intermediate Similarity	NPC268607
0.7748	Intermediate Similarity	NPC229545
0.7748	Intermediate Similarity	NPC257213
0.7748	Intermediate Similarity	NPC304876
0.7748	Intermediate Similarity	NPC134685
0.7748	Intermediate Similarity	NPC158333
0.7748	Intermediate Similarity	NPC248265
0.7748	Intermediate Similarity	NPC1173
0.7748	Intermediate Similarity	NPC249471
0.7748	Intermediate Similarity	NPC265395
0.7748	Intermediate Similarity	NPC473414
0.7748	Intermediate Similarity	NPC237549
0.7748	Intermediate Similarity	NPC256142
0.7748	Intermediate Similarity	NPC11588
0.7748	Intermediate Similarity	NPC219419
0.7748	Intermediate Similarity	NPC472030
0.7748	Intermediate Similarity	NPC242262
0.7748	Intermediate Similarity	NPC472005
0.7748	Intermediate Similarity	NPC472022
0.7746	Intermediate Similarity	NPC477896
0.7744	Intermediate Similarity	NPC202015
0.7737	Intermediate Similarity	NPC236405
0.7727	Intermediate Similarity	NPC222968
0.7727	Intermediate Similarity	NPC80605
0.7727	Intermediate Similarity	NPC323440
0.7727	Intermediate Similarity	NPC471553
0.7724	Intermediate Similarity	NPC41481
0.7724	Intermediate Similarity	NPC291599
0.7724	Intermediate Similarity	NPC27377
0.7724	Intermediate Similarity	NPC16912
0.7724	Intermediate Similarity	NPC87448
0.7724	Intermediate Similarity	NPC97947
0.7724	Intermediate Similarity	NPC472576
0.7724	Intermediate Similarity	NPC118080
0.7722	Intermediate Similarity	NPC102465
0.7718	Intermediate Similarity	NPC471970
0.7712	Intermediate Similarity	NPC469771
0.7712	Intermediate Similarity	NPC472393
0.7712	Intermediate Similarity	NPC469417
0.7703	Intermediate Similarity	NPC469513
0.7703	Intermediate Similarity	NPC474241
0.7697	Intermediate Similarity	NPC112523
0.7697	Intermediate Similarity	NPC155329
0.7697	Intermediate Similarity	NPC259144
0.7697	Intermediate Similarity	NPC228204
0.7697	Intermediate Similarity	NPC114410
0.7697	Intermediate Similarity	NPC26033
0.7697	Intermediate Similarity	NPC114357
0.7692	Intermediate Similarity	NPC472551
0.7692	Intermediate Similarity	NPC472545
0.7692	Intermediate Similarity	NPC294458
0.7687	Intermediate Similarity	NPC472679
0.7687	Intermediate Similarity	NPC475122
0.7687	Intermediate Similarity	NPC472680
0.7676	Intermediate Similarity	NPC310662
0.7671	Intermediate Similarity	NPC34012
0.7669	Intermediate Similarity	NPC472697
0.7669	Intermediate Similarity	NPC472698
0.7664	Intermediate Similarity	NPC246166
0.7662	Intermediate Similarity	NPC471102
0.7655	Intermediate Similarity	NPC97667
0.7655	Intermediate Similarity	NPC90614
0.7655	Intermediate Similarity	NPC183270
0.7655	Intermediate Similarity	NPC171207
0.7655	Intermediate Similarity	NPC474250
0.7655	Intermediate Similarity	NPC477904
0.7651	Intermediate Similarity	NPC205389
0.7647	Intermediate Similarity	NPC108286
0.7635	Intermediate Similarity	NPC472575
0.7635	Intermediate Similarity	NPC200471
0.7635	Intermediate Similarity	NPC177940
0.7635	Intermediate Similarity	NPC473088
0.7635	Intermediate Similarity	NPC472572
0.7635	Intermediate Similarity	NPC29704
0.7635	Intermediate Similarity	NPC471100
0.7635	Intermediate Similarity	NPC471104
0.7635	Intermediate Similarity	NPC171525
0.7635	Intermediate Similarity	NPC472571
0.7635	Intermediate Similarity	NPC470157
0.7635	Intermediate Similarity	NPC184817
0.7635	Intermediate Similarity	NPC476973
0.7635	Intermediate Similarity	NPC174982
0.7635	Intermediate Similarity	NPC471107
0.7635	Intermediate Similarity	NPC96903
0.7635	Intermediate Similarity	NPC472568
0.7635	Intermediate Similarity	NPC158663
0.7635	Intermediate Similarity	NPC70403
0.7635	Intermediate Similarity	NPC470159
0.7635	Intermediate Similarity	NPC469349
0.7634	Intermediate Similarity	NPC215419
0.7632	Intermediate Similarity	NPC133430
0.7632	Intermediate Similarity	NPC77719
0.7632	Intermediate Similarity	NPC469477
0.7628	Intermediate Similarity	NPC55744
0.7626	Intermediate Similarity	NPC115797
0.7626	Intermediate Similarity	NPC478162
0.7626	Intermediate Similarity	NPC478165
0.7626	Intermediate Similarity	NPC51448
0.7622	Intermediate Similarity	NPC23894
0.7622	Intermediate Similarity	NPC477893
0.7619	Intermediate Similarity	NPC477894
0.7619	Intermediate Similarity	NPC95449
0.7616	Intermediate Similarity	NPC470153
0.761	Intermediate Similarity	NPC469420
0.7609	Intermediate Similarity	NPC476033
0.7609	Intermediate Similarity	NPC79608
0.7606	Intermediate Similarity	NPC15850
0.7603	Intermediate Similarity	NPC242355
0.7603	Intermediate Similarity	NPC224491
0.7603	Intermediate Similarity	NPC187566
0.76	Intermediate Similarity	NPC473215
0.7597	Intermediate Similarity	NPC265513
0.7591	Intermediate Similarity	NPC318067
0.7584	Intermediate Similarity	NPC474935
0.7584	Intermediate Similarity	NPC170668
0.7584	Intermediate Similarity	NPC469856
0.7584	Intermediate Similarity	NPC469854
0.7574	Intermediate Similarity	NPC475328
0.7569	Intermediate Similarity	NPC472374
0.7569	Intermediate Similarity	NPC472372
0.7568	Intermediate Similarity	NPC476974
0.7568	Intermediate Similarity	NPC25768
0.7568	Intermediate Similarity	NPC471972
0.7568	Intermediate Similarity	NPC95810
0.7568	Intermediate Similarity	NPC475759
0.7568	Intermediate Similarity	NPC57628
0.7568	Intermediate Similarity	NPC163719
0.7568	Intermediate Similarity	NPC472573
0.7568	Intermediate Similarity	NPC30846
0.7568	Intermediate Similarity	NPC472570

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 NPC144257 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	242
0.1-0.2	633
0.2-0.3	1552
0.3-0.4	3140
0.4-0.5	2360
0.5-0.6	1009
0.6-0.7	204
0.7-0.8	10
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7734	Intermediate Similarity	NPD4141	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7457	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD7966	Clinical (unspecified phase)
0.7305	Intermediate Similarity	NPD6007	Clinical (unspecified phase)
0.7301	Intermediate Similarity	NPD7799	Discontinued
0.7299	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.7292	Intermediate Similarity	NPD7961	Discontinued
0.7285	Intermediate Similarity	NPD7236	Approved
0.7219	Intermediate Similarity	NPD8434	Phase 2
0.7101	Intermediate Similarity	NPD8407	Phase 2
0.709	Intermediate Similarity	NPD6858	Approved
0.709	Intermediate Similarity	NPD7094	Approved
0.708	Intermediate Similarity	NPD7610	Discontinued
0.7051	Intermediate Similarity	NPD7239	Suspended
0.7034	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7029	Intermediate Similarity	NPD7009	Phase 2
0.7024	Intermediate Similarity	NPD8368	Discontinued
0.6937	Remote Similarity	NPD5760	Phase 2
0.6937	Remote Similarity	NPD5761	Phase 2
0.6928	Remote Similarity	NPD4628	Phase 3
0.6889	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.6861	Remote Similarity	NPD2629	Approved
0.6797	Remote Similarity	NPD3495	Discontinued
0.6794	Remote Similarity	NPD1931	Clinical (unspecified phase)
0.6794	Remote Similarity	NPD1929	Approved
0.6794	Remote Similarity	NPD1930	Approved
0.6788	Remote Similarity	NPD6010	Discontinued
0.6767	Remote Similarity	NPD6685	Approved
0.675	Remote Similarity	NPD4380	Phase 2
0.6743	Remote Similarity	NPD8435	Approved
0.6743	Remote Similarity	NPD8360	Approved
0.6743	Remote Similarity	NPD8361	Approved
0.6724	Remote Similarity	NPD8150	Discontinued
0.6692	Remote Similarity	NPD5048	Discontinued
0.6692	Remote Similarity	NPD2066	Phase 3
0.6691	Remote Similarity	NPD3317	Approved
0.6667	Remote Similarity	NPD6647	Phase 2
0.6667	Remote Similarity	NPD7084	Phase 3
0.6667	Remote Similarity	NPD7741	Discontinued
0.6667	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6646	Remote Similarity	NPD7057	Phase 3
0.6646	Remote Similarity	NPD7058	Phase 2
0.6629	Remote Similarity	NPD8424	Clinical (unspecified phase)
0.6626	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6619	Remote Similarity	NPD5951	Approved
0.6614	Remote Similarity	NPD7631	Approved
0.6603	Remote Similarity	NPD8166	Discontinued
0.6601	Remote Similarity	NPD7305	Phase 1
0.6591	Remote Similarity	NPD1932	Approved
0.6573	Remote Similarity	NPD5126	Approved
0.6573	Remote Similarity	NPD5125	Phase 3
0.6571	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6569	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6566	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.6565	Remote Similarity	NPD7798	Approved
0.6562	Remote Similarity	NPD5122	Clinical (unspecified phase)
0.655	Remote Similarity	NPD8470	Clinical (unspecified phase)
0.6549	Remote Similarity	NPD6054	Approved
0.6544	Remote Similarity	NPD2329	Discontinued
0.6543	Remote Similarity	NPD6599	Discontinued
0.6541	Remote Similarity	NPD5765	Approved
0.6538	Remote Similarity	NPD2800	Approved
0.6535	Remote Similarity	NPD7609	Phase 3
0.6532	Remote Similarity	NPD6764	Approved
0.6532	Remote Similarity	NPD6765	Approved
0.6531	Remote Similarity	NPD1470	Approved
0.6528	Remote Similarity	NPD4879	Approved
0.6527	Remote Similarity	NPD5494	Approved
0.6524	Remote Similarity	NPD7819	Suspended
0.6519	Remote Similarity	NPD8485	Approved
0.6506	Remote Similarity	NPD7075	Discontinued
0.6496	Remote Similarity	NPD2067	Discontinued
0.6493	Remote Similarity	NPD1237	Approved
0.6485	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6481	Remote Similarity	NPD6591	Clinical (unspecified phase)
0.6481	Remote Similarity	NPD7458	Discontinued
0.648	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6467	Remote Similarity	NPD7008	Discontinued
0.6458	Remote Similarity	NPD6370	Approved
0.6458	Remote Similarity	NPD7163	Clinical (unspecified phase)
0.6457	Remote Similarity	NPD8312	Approved
0.6457	Remote Similarity	NPD8313	Approved
0.6438	Remote Similarity	NPD4878	Approved
0.6438	Remote Similarity	NPD3972	Approved
0.6424	Remote Similarity	NPD3764	Approved
0.6424	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6415	Remote Similarity	NPD3300	Phase 2
0.6413	Remote Similarity	NPD8486	Clinical (unspecified phase)
0.641	Remote Similarity	NPD2346	Discontinued
0.6407	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6403	Remote Similarity	NPD6912	Phase 3
0.64	Remote Similarity	NPD7055	Discontinued
0.64	Remote Similarity	NPD2613	Approved
0.6398	Remote Similarity	NPD6273	Approved
0.6395	Remote Similarity	NPD3818	Discontinued
0.6391	Remote Similarity	NPD8127	Discontinued
0.6389	Remote Similarity	NPD6015	Approved
0.6389	Remote Similarity	NPD6016	Approved
0.6387	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.6384	Remote Similarity	NPD6785	Approved
0.6384	Remote Similarity	NPD6784	Approved
0.6383	Remote Similarity	NPD690	Clinical (unspecified phase)
0.6382	Remote Similarity	NPD6663	Approved
0.6377	Remote Similarity	NPD4634	Approved
0.637	Remote Similarity	NPD7492	Approved
0.637	Remote Similarity	NPD5909	Discontinued
0.637	Remote Similarity	NPD1201	Approved
0.6364	Remote Similarity	NPD1934	Approved
0.6364	Remote Similarity	NPD6801	Discontinued
0.6358	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6351	Remote Similarity	NPD7736	Approved
0.6347	Remote Similarity	NPD3882	Suspended
0.6346	Remote Similarity	NPD2796	Approved
0.6345	Remote Similarity	NPD2932	Approved
0.6345	Remote Similarity	NPD5988	Approved
0.6338	Remote Similarity	NPD4198	Discontinued
0.6337	Remote Similarity	NPD7473	Discontinued
0.6335	Remote Similarity	NPD2534	Approved
0.6335	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6335	Remote Similarity	NPD2532	Approved
0.6335	Remote Similarity	NPD8389	Clinical (unspecified phase)
0.6335	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6335	Remote Similarity	NPD2533	Approved
0.6327	Remote Similarity	NPD6616	Approved
0.6319	Remote Similarity	NPD6319	Approved
0.6319	Remote Similarity	NPD6059	Approved
0.6316	Remote Similarity	NPD2313	Discontinued
0.6312	Remote Similarity	NPD2652	Approved
0.6312	Remote Similarity	NPD2650	Approved
0.6308	Remote Similarity	NPD5282	Discontinued
0.6306	Remote Similarity	NPD1471	Phase 3
0.6306	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6306	Remote Similarity	NPD2344	Approved
0.6306	Remote Similarity	NPD7702	Clinical (unspecified phase)
0.6304	Remote Similarity	NPD2182	Approved
0.6302	Remote Similarity	NPD8462	Phase 1
0.6286	Remote Similarity	NPD8297	Approved
0.6284	Remote Similarity	NPD7078	Approved
0.6282	Remote Similarity	NPD1510	Phase 2
0.6282	Remote Similarity	NPD2799	Discontinued
0.628	Remote Similarity	NPD3226	Approved
0.6278	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6275	Remote Similarity	NPD2571	Approved
0.6275	Remote Similarity	NPD3087	Approved
0.6275	Remote Similarity	NPD3614	Approved
0.6275	Remote Similarity	NPD4746	Phase 3
0.6275	Remote Similarity	NPD2570	Approved
0.6275	Remote Similarity	NPD2572	Clinical (unspecified phase)
0.6275	Remote Similarity	NPD2566	Approved
0.6275	Remote Similarity	NPD3088	Approved
0.6275	Remote Similarity	NPD4745	Approved
0.6275	Remote Similarity	NPD3089	Approved
0.6275	Remote Similarity	NPD2574	Discontinued
0.6275	Remote Similarity	NPD2573	Approved
0.6275	Remote Similarity	NPD3615	Approved
0.6275	Remote Similarity	NPD3090	Approved
0.6275	Remote Similarity	NPD3616	Approved
0.6273	Remote Similarity	NPD6799	Approved
0.6273	Remote Similarity	NPD8165	Discontinued
0.6267	Remote Similarity	NPD2798	Approved
0.6266	Remote Similarity	NPD1549	Phase 2
0.626	Remote Similarity	NPD1693	Approved
0.6259	Remote Similarity	NPD2608	Approved
0.6259	Remote Similarity	NPD4217	Approved
0.6259	Remote Similarity	NPD1317	Discontinued
0.6259	Remote Similarity	NPD2610	Approved
0.6259	Remote Similarity	NPD4218	Approved
0.6259	Remote Similarity	NPD4215	Approved
0.6259	Remote Similarity	NPD3132	Approved
0.6259	Remote Similarity	NPD3131	Approved
0.6259	Remote Similarity	NPD2612	Approved
0.6259	Remote Similarity	NPD4216	Approved
0.6259	Remote Similarity	NPD2611	Approved
0.6259	Remote Similarity	NPD2609	Approved
0.6258	Remote Similarity	NPD6651	Approved
0.6256	Remote Similarity	NPD8404	Phase 2
0.625	Remote Similarity	NPD7274	Clinical (unspecified phase)
0.625	Remote Similarity	NPD7685	Pre-registration
0.625	Remote Similarity	NPD6190	Approved
0.625	Remote Similarity	NPD6065	Approved
0.625	Remote Similarity	NPD4965	Approved
0.625	Remote Similarity	NPD4966	Approved
0.625	Remote Similarity	NPD6559	Discontinued
0.625	Remote Similarity	NPD4967	Phase 2
0.6242	Remote Similarity	NPD6099	Approved
0.6242	Remote Similarity	NPD7028	Phase 2
0.6242	Remote Similarity	NPD6100	Approved
0.6235	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6235	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6234	Remote Similarity	NPD943	Approved
0.6233	Remote Similarity	NPD3019	Approved
0.6231	Remote Similarity	NPD1088	Approved
0.6228	Remote Similarity	NPD2801	Approved
0.6226	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6225	Remote Similarity	NPD5736	Approved
0.6224	Remote Similarity	NPD7115	Discovery
0.622	Remote Similarity	NPD650	Approved
0.6216	Remote Similarity	NPD7700	Phase 2
0.6216	Remote Similarity	NPD7699	Phase 2
0.6212	Remote Similarity	NPD1989	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