NPASS Compound

Structure

NPC262324 OpenBabel07101719152D 43 50 0 0 1 0 0 0 0 0999 V2000 -3.8124 -4.5129 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -2.5000 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 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 -5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3364 -1.5827 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 1.7321 -3.0000 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 0.7431 -0.6691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0899 -4.6940 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1193 -3.1994 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 -3.1080 -6.0952 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 4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0034 -5.1007 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9854 -3.6994 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.3272 -2.2213 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.6581 -1.4781 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.1962 -3.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.3218 -2.1168 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.4641 -2.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.0215 -6.5020 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.8218 -1.2507 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.7285 -3.0303 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 23 1 0 0 0 0 4 36 1 0 0 0 0 5 6 2 0 0 0 0 5 7 1 0 0 0 0 6 8 1 0 0 0 0 7 9 2 0 0 0 0 8 24 2 0 0 0 0 9 24 1 0 0 0 0 10 13 1 0 0 0 0 10 25 2 0 0 0 0 11 15 1 0 0 0 0 11 28 1 0 0 0 0 12 14 1 0 0 0 0 12 30 1 0 0 0 0 13 34 1 0 0 0 0 14 37 1 0 0 0 0 16 23 2 0 0 0 0 17 25 1 0 0 0 0 17 29 1 0 0 0 0 18 26 1 0 0 0 0 19 31 1 0 0 0 0 19 32 1 0 0 0 0 20 23 1 0 0 0 0 20 39 1 0 0 0 0 21 37 1 0 0 0 0 21 38 1 0 0 0 0 22 35 1 0 0 0 0 22 42 1 0 0 0 0 25 35 1 0 0 0 0 26 16 1 6 0 0 0 26 43 1 0 0 0 0 27 18 1 6 0 0 0 27 28 1 0 0 0 0 27 33 1 0 0 0 0 28 37 1 1 0 0 0 29 24 1 6 0 0 0 29 42 1 0 0 0 0 30 34 1 1 0 0 0 30 36 1 0 0 0 0 31 34 1 1 0 0 0 31 35 1 0 0 0 0 32 36 1 6 0 0 0 32 40 1 0 0 0 0 33 41 2 0 0 0 0 33 43 1 0 0 0 0 34 2 1 1 0 0 0 35 3 1 6 0 0 0 36 38 1 6 0 0 0 37 38 1 6 0 0 0 38 15 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	586.37
Volume:	625.485
LogP:	5.094
LogD:	3.896
LogS:	-5.349
# Rotatable Bonds:	4
TPSA:	75.99
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	8
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.295
Synthetic Accessibility Score:	5.633
Fsp3:	0.711
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.081
MDCK Permeability:	1.7518595996079966e-05
Pgp-inhibitor:	0.05
Pgp-substrate:	0.055
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.919
30% Bioavailability (F30%):	0.914

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.366
Plasma Protein Binding (PPB):	94.40340423583984%
Volume Distribution (VD):	1.488
Pgp-substrate:	2.5578386783599854%

ADMET: Metabolism

CYP1A2-inhibitor:	0.015
CYP1A2-substrate:	0.196
CYP2C19-inhibitor:	0.167
CYP2C19-substrate:	0.772
CYP2C9-inhibitor:	0.39
CYP2C9-substrate:	0.074
CYP2D6-inhibitor:	0.032
CYP2D6-substrate:	0.117
CYP3A4-inhibitor:	0.867
CYP3A4-substrate:	0.708

ADMET: Excretion

Clearance (CL):	7.253
Half-life (T1/2):	0.093

ADMET: Toxicity

hERG Blockers:	0.688
Human Hepatotoxicity (H-HT):	0.813
Drug-inuced Liver Injury (DILI):	0.25
AMES Toxicity:	0.02
Rat Oral Acute Toxicity:	0.846
Maximum Recommended Daily Dose:	0.986
Skin Sensitization:	0.904
Carcinogencity:	0.027
Eye Corrosion:	0.003
Eye Irritation:	0.013
Respiratory Toxicity:	0.962

Download Data

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

Natural Product: NPC262324

Natural Product ID:	NPC262324
*Common Name:**	Dichapetalin L
IUPAC Name:	n.a.
Synonyms:	Dichapetalin L
Standard InCHIKey:	CXFAPKZJDHSDJC-NNLSLSRSSA-N
Standard InCHI:	InChI=1S/C38H50O5/c1-23(20-39)16-26-18-27(33(41)43-26)28-11-15-38-21-37(28,38)14-12-30-34(2)13-10-25-17-29(24-8-6-5-7-9-24)42-22-35(25,3)31(34)19-32(40)36(30,38)4/h5-10,16,26-32,39-40H,11-15,17-22H2,1-4H3/b23-16+/t26-,27-,28-,29-,30+,31+,32+,34+,35-,36-,37+,38+/m0/s1
SMILES:	OC/C(=C/[C@@H]1OC(=O)[C@@H](C1)[C@@H]1CC[C@@]23[C@]1(CC[C@H]1[C@@]3(C)[C@H](O)C[C@@H]3[C@]1(C)CC=C1[C@]3(C)CO[C@@H](C1)c1ccccc1)C2)/C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL445723
PubChem CID:	11685706
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids [CHEMONTID:0002380] Limonoids

*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
NPO9878	Dichapetalum gelonioides	Species	Dichapetalaceae	Eukaryota	stem bark	Philippines	n.a.	PMID[16562829]
NPO9878	Dichapetalum gelonioides	Species	Dichapetalaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24597894]
NPO9878	Dichapetalum gelonioides	Species	Dichapetalaceae	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

Activity Type	# Activity
Cell Line	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1034	Cell Line	Lu1	Homo sapiens	ED50	=	1.0	ug ml-1	PMID[548005]
NPT858	Cell Line	LNCaP	Homo sapiens	ED50	=	1.1	ug ml-1	PMID[548005]
NPT2345	Cell Line	SW626	Homo sapiens	ED50	=	8.3	ug ml-1	PMID[548005]
NPT83	Cell Line	MCF7	Homo sapiens	ED50	=	2.1	ug ml-1	PMID[548005]
NPT737	Cell Line	HUVEC	Homo sapiens	ED50	=	4.2	ug ml-1	PMID[548005]

☑ 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 NPC262324 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	297
0.1-0.2	1148
0.2-0.3	2306
0.3-0.4	4711
0.4-0.5	9130
0.5-0.6	19041
0.6-0.7	5136
0.7-0.8	897
0.8-0.85	19
0.85-0.9	5
0.9-0.95	4
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9847	High Similarity	NPC79921
0.9846	High Similarity	NPC243893
0.9692	High Similarity	NPC471864
0.9021	High Similarity	NPC261659
0.9014	High Similarity	NPC253591
0.8944	High Similarity	NPC475417
0.8944	High Similarity	NPC475561
0.875	High Similarity	NPC203486
0.8667	High Similarity	NPC470278
0.8613	High Similarity	NPC48929
0.8511	High Similarity	NPC471862
0.8429	Intermediate Similarity	NPC475373
0.8394	Intermediate Similarity	NPC72915
0.8378	Intermediate Similarity	NPC472658
0.8378	Intermediate Similarity	NPC472657
0.8377	Intermediate Similarity	NPC471861
0.837	Intermediate Similarity	NPC253681
0.837	Intermediate Similarity	NPC5486
0.8322	Intermediate Similarity	NPC471856
0.8296	Intermediate Similarity	NPC470816
0.8284	Intermediate Similarity	NPC307139
0.8243	Intermediate Similarity	NPC279442
0.8235	Intermediate Similarity	NPC169913
0.8227	Intermediate Similarity	NPC472374
0.8227	Intermediate Similarity	NPC472372
0.8214	Intermediate Similarity	NPC329913
0.8214	Intermediate Similarity	NPC126516
0.8209	Intermediate Similarity	NPC182333
0.8209	Intermediate Similarity	NPC273336
0.8188	Intermediate Similarity	NPC472548
0.8188	Intermediate Similarity	NPC475138
0.8182	Intermediate Similarity	NPC234548
0.8182	Intermediate Similarity	NPC248287
0.8162	Intermediate Similarity	NPC275576
0.8156	Intermediate Similarity	NPC477893
0.8148	Intermediate Similarity	NPC77691
0.8129	Intermediate Similarity	NPC471858
0.8125	Intermediate Similarity	NPC224491
0.8102	Intermediate Similarity	NPC473220
0.8102	Intermediate Similarity	NPC470753
0.8095	Intermediate Similarity	NPC473602
0.8082	Intermediate Similarity	NPC475122
0.8079	Intermediate Similarity	NPC472549
0.8077	Intermediate Similarity	NPC471850
0.8067	Intermediate Similarity	NPC477905
0.8058	Intermediate Similarity	NPC147561
0.8058	Intermediate Similarity	NPC472388
0.8056	Intermediate Similarity	NPC275592
0.8056	Intermediate Similarity	NPC473440
0.8056	Intermediate Similarity	NPC90614
0.8056	Intermediate Similarity	NPC100913
0.8042	Intermediate Similarity	NPC249817
0.8042	Intermediate Similarity	NPC39549
0.8039	Intermediate Similarity	NPC476784
0.8029	Intermediate Similarity	NPC470765
0.8028	Intermediate Similarity	NPC477896
0.8027	Intermediate Similarity	NPC96903
0.8027	Intermediate Similarity	NPC174982
0.8027	Intermediate Similarity	NPC472568
0.8027	Intermediate Similarity	NPC158663
0.8027	Intermediate Similarity	NPC171525
0.8027	Intermediate Similarity	NPC470157
0.8027	Intermediate Similarity	NPC184817
0.8027	Intermediate Similarity	NPC200471
0.8027	Intermediate Similarity	NPC470159
0.8027	Intermediate Similarity	NPC473088
0.8027	Intermediate Similarity	NPC472556
0.8027	Intermediate Similarity	NPC469349
0.8027	Intermediate Similarity	NPC472571
0.8027	Intermediate Similarity	NPC476973
0.8027	Intermediate Similarity	NPC471104
0.8027	Intermediate Similarity	NPC177940
0.8027	Intermediate Similarity	NPC29704
0.8027	Intermediate Similarity	NPC70403
0.8027	Intermediate Similarity	NPC472572
0.8027	Intermediate Similarity	NPC472575
0.8014	Intermediate Similarity	NPC131966
0.8014	Intermediate Similarity	NPC472656
0.8014	Intermediate Similarity	NPC163087
0.8014	Intermediate Similarity	NPC91703
0.8014	Intermediate Similarity	NPC191387
0.8014	Intermediate Similarity	NPC477894
0.8	Intermediate Similarity	NPC27377
0.8	Intermediate Similarity	NPC41481
0.8	Intermediate Similarity	NPC291599
0.8	Intermediate Similarity	NPC293831
0.8	Intermediate Similarity	NPC472576
0.8	Intermediate Similarity	NPC16912
0.8	Intermediate Similarity	NPC87448
0.8	Intermediate Similarity	NPC118080
0.8	Intermediate Similarity	NPC369
0.8	Intermediate Similarity	NPC97947
0.7987	Intermediate Similarity	NPC266265
0.7987	Intermediate Similarity	NPC471101
0.7987	Intermediate Similarity	NPC270590
0.7987	Intermediate Similarity	NPC471859
0.7987	Intermediate Similarity	NPC471860
0.7987	Intermediate Similarity	NPC92293
0.7987	Intermediate Similarity	NPC301556
0.7986	Intermediate Similarity	NPC198621
0.7986	Intermediate Similarity	NPC216940
0.7986	Intermediate Similarity	NPC225103
0.7986	Intermediate Similarity	NPC475482
0.7986	Intermediate Similarity	NPC22676
0.7985	Intermediate Similarity	NPC183339
0.7985	Intermediate Similarity	NPC133389
0.7985	Intermediate Similarity	NPC234337
0.7973	Intermediate Similarity	NPC474935
0.7972	Intermediate Similarity	NPC472551
0.7972	Intermediate Similarity	NPC173569
0.7972	Intermediate Similarity	NPC472545
0.7972	Intermediate Similarity	NPC477874
0.7971	Intermediate Similarity	NPC171007
0.7971	Intermediate Similarity	NPC190849
0.7959	Intermediate Similarity	NPC472570
0.7959	Intermediate Similarity	NPC188865
0.7959	Intermediate Similarity	NPC57628
0.7959	Intermediate Similarity	NPC25768
0.7959	Intermediate Similarity	NPC11685
0.7959	Intermediate Similarity	NPC95810
0.7959	Intermediate Similarity	NPC472573
0.7959	Intermediate Similarity	NPC475759
0.7959	Intermediate Similarity	NPC70716
0.7959	Intermediate Similarity	NPC241951
0.7959	Intermediate Similarity	NPC95265
0.7959	Intermediate Similarity	NPC163719
0.7959	Intermediate Similarity	NPC125106
0.7959	Intermediate Similarity	NPC470152
0.7959	Intermediate Similarity	NPC472569
0.7959	Intermediate Similarity	NPC476974
0.7945	Intermediate Similarity	NPC140021
0.7945	Intermediate Similarity	NPC172311
0.7945	Intermediate Similarity	NPC475135
0.7933	Intermediate Similarity	NPC325032
0.7933	Intermediate Similarity	NPC125033
0.7933	Intermediate Similarity	NPC477483
0.7931	Intermediate Similarity	NPC183270
0.7931	Intermediate Similarity	NPC472547
0.7931	Intermediate Similarity	NPC477904
0.7931	Intermediate Similarity	NPC97667
0.7931	Intermediate Similarity	NPC475400
0.7931	Intermediate Similarity	NPC171207
0.7929	Intermediate Similarity	NPC473443
0.7929	Intermediate Similarity	NPC49272
0.7919	Intermediate Similarity	NPC132652
0.7919	Intermediate Similarity	NPC281717
0.7905	Intermediate Similarity	NPC477207
0.7902	Intermediate Similarity	NPC473216
0.7902	Intermediate Similarity	NPC11266
0.7902	Intermediate Similarity	NPC473399
0.7895	Intermediate Similarity	NPC45794
0.7891	Intermediate Similarity	NPC477468
0.7881	Intermediate Similarity	NPC470153
0.7871	Intermediate Similarity	NPC309991
0.7871	Intermediate Similarity	NPC326328
0.7871	Intermediate Similarity	NPC323356
0.7871	Intermediate Similarity	NPC471138
0.7867	Intermediate Similarity	NPC476975
0.7867	Intermediate Similarity	NPC473215
0.7862	Intermediate Similarity	NPC210591
0.7862	Intermediate Similarity	NPC214550
0.7862	Intermediate Similarity	NPC472395
0.7862	Intermediate Similarity	NPC475652
0.7862	Intermediate Similarity	NPC472371
0.7857	Intermediate Similarity	NPC318447
0.7857	Intermediate Similarity	NPC322048
0.7853	Intermediate Similarity	NPC475244
0.7852	Intermediate Similarity	NPC478263
0.7852	Intermediate Similarity	NPC240115
0.7848	Intermediate Similarity	NPC477491
0.7847	Intermediate Similarity	NPC472804
0.7843	Intermediate Similarity	NPC473611
0.7843	Intermediate Similarity	NPC132599
0.7843	Intermediate Similarity	NPC469730
0.7843	Intermediate Similarity	NPC473632
0.7838	Intermediate Similarity	NPC470273
0.7832	Intermediate Similarity	NPC310662
0.7832	Intermediate Similarity	NPC471911
0.7832	Intermediate Similarity	NPC474608
0.7832	Intermediate Similarity	NPC4242
0.7829	Intermediate Similarity	NPC233581
0.7829	Intermediate Similarity	NPC469647
0.7829	Intermediate Similarity	NPC22571
0.7829	Intermediate Similarity	NPC138641
0.7829	Intermediate Similarity	NPC283875
0.7829	Intermediate Similarity	NPC469648
0.7829	Intermediate Similarity	NPC145649
0.7823	Intermediate Similarity	NPC472546
0.7823	Intermediate Similarity	NPC472801
0.7823	Intermediate Similarity	NPC27518
0.7823	Intermediate Similarity	NPC63737
0.7823	Intermediate Similarity	NPC192658
0.7823	Intermediate Similarity	NPC183540
0.7823	Intermediate Similarity	NPC34012
0.7823	Intermediate Similarity	NPC304110
0.782	Intermediate Similarity	NPC470820
0.7817	Intermediate Similarity	NPC475493
0.7817	Intermediate Similarity	NPC471880
0.7817	Intermediate Similarity	NPC80599
0.7817	Intermediate Similarity	NPC472394

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 NPC262324 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	244
0.1-0.2	752
0.2-0.3	1467
0.3-0.4	2975
0.4-0.5	2317
0.5-0.6	1188
0.6-0.7	191
0.7-0.8	16
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
0.797	Intermediate Similarity	NPD7741	Discontinued
0.7905	Intermediate Similarity	NPD7236	Approved
0.7692	Intermediate Similarity	NPD6663	Approved
0.7647	Intermediate Similarity	NPD7239	Suspended
0.7546	Intermediate Similarity	NPD7799	Discontinued
0.7535	Intermediate Similarity	NPD5736	Approved
0.7451	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7431	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7417	Intermediate Similarity	NPD8166	Discontinued
0.7407	Intermediate Similarity	NPD2629	Approved
0.7388	Intermediate Similarity	NPD6858	Approved
0.7388	Intermediate Similarity	NPD7094	Approved
0.7346	Intermediate Similarity	NPD8127	Discontinued
0.7343	Intermediate Similarity	NPD6007	Clinical (unspecified phase)
0.7226	Intermediate Similarity	NPD4198	Discontinued
0.7222	Intermediate Similarity	NPD6085	Phase 2
0.7222	Intermediate Similarity	NPD5740	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD6002	Phase 3
0.7219	Intermediate Similarity	NPD6004	Phase 3
0.7219	Intermediate Similarity	NPD6005	Phase 3
0.7211	Intermediate Similarity	NPD8032	Phase 2
0.7211	Intermediate Similarity	NPD7961	Discontinued
0.7205	Intermediate Similarity	NPD7057	Phase 3
0.7205	Intermediate Similarity	NPD7058	Phase 2
0.72	Intermediate Similarity	NPD7305	Phase 1
0.7192	Intermediate Similarity	NPD7008	Discontinued
0.7179	Intermediate Similarity	NPD6273	Approved
0.7163	Intermediate Similarity	NPD7457	Clinical (unspecified phase)
0.7162	Intermediate Similarity	NPD4140	Approved
0.7126	Intermediate Similarity	NPD7228	Approved
0.7099	Intermediate Similarity	NPD4967	Phase 2
0.7099	Intermediate Similarity	NPD4965	Approved
0.7099	Intermediate Similarity	NPD4966	Approved
0.7095	Intermediate Similarity	NPD7714	Approved
0.7095	Intermediate Similarity	NPD7715	Approved
0.7092	Intermediate Similarity	NPD5126	Approved
0.7092	Intermediate Similarity	NPD2932	Approved
0.7092	Intermediate Similarity	NPD3019	Approved
0.7092	Intermediate Similarity	NPD5125	Phase 3
0.7044	Intermediate Similarity	NPD6591	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD3764	Approved
0.7019	Intermediate Similarity	NPD37	Approved
0.6993	Remote Similarity	NPD5762	Approved
0.6993	Remote Similarity	NPD5763	Approved
0.6985	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD5760	Phase 2
0.6975	Remote Similarity	NPD5761	Phase 2
0.6972	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6968	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD6010	Discontinued
0.694	Remote Similarity	NPD6685	Approved
0.6909	Remote Similarity	NPD6234	Discontinued
0.6906	Remote Similarity	NPD5951	Approved
0.6897	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD6355	Discontinued
0.6887	Remote Similarity	NPD5735	Approved
0.6883	Remote Similarity	NPD7702	Clinical (unspecified phase)
0.6882	Remote Similarity	NPD8470	Clinical (unspecified phase)
0.686	Remote Similarity	NPD7240	Approved
0.6859	Remote Similarity	NPD7003	Approved
0.6859	Remote Similarity	NPD4628	Phase 3
0.6857	Remote Similarity	NPD8424	Clinical (unspecified phase)
0.6853	Remote Similarity	NPD7163	Clinical (unspecified phase)
0.6838	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD4869	Clinical (unspecified phase)
0.6831	Remote Similarity	NPD3091	Approved
0.6826	Remote Similarity	NPD7199	Phase 2
0.6821	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6806	Remote Similarity	NPD3026	Approved
0.6806	Remote Similarity	NPD3023	Approved
0.6797	Remote Similarity	NPD7097	Phase 1
0.679	Remote Similarity	NPD7028	Phase 2
0.6783	Remote Similarity	NPD3025	Approved
0.6783	Remote Similarity	NPD3024	Approved
0.6768	Remote Similarity	NPD8455	Phase 2
0.6761	Remote Similarity	NPD7610	Discontinued
0.6761	Remote Similarity	NPD8434	Phase 2
0.6759	Remote Similarity	NPD3092	Approved
0.6753	Remote Similarity	NPD7033	Discontinued
0.6752	Remote Similarity	NPD4110	Phase 3
0.6752	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6748	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6743	Remote Similarity	NPD8407	Phase 2
0.6742	Remote Similarity	NPD7639	Approved
0.6742	Remote Similarity	NPD7640	Approved
0.6741	Remote Similarity	NPD5048	Discontinued
0.6736	Remote Similarity	NPD3095	Discontinued
0.6732	Remote Similarity	NPD6353	Approved
0.6728	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6728	Remote Similarity	NPD7458	Discontinued
0.6716	Remote Similarity	NPD5765	Approved
0.6716	Remote Similarity	NPD5738	Clinical (unspecified phase)
0.6716	Remote Similarity	NPD6647	Phase 2
0.671	Remote Similarity	NPD6099	Approved
0.671	Remote Similarity	NPD6100	Approved
0.671	Remote Similarity	NPD7137	Phase 2
0.6709	Remote Similarity	NPD7910	Clinical (unspecified phase)
0.6689	Remote Similarity	NPD3094	Phase 2
0.6685	Remote Similarity	NPD8360	Approved
0.6685	Remote Similarity	NPD8361	Approved
0.6667	Remote Similarity	NPD7055	Discontinued
0.6667	Remote Similarity	NPD5909	Discontinued
0.6667	Remote Similarity	NPD8368	Discontinued
0.6667	Remote Similarity	NPD5327	Phase 3
0.6667	Remote Similarity	NPD6764	Approved
0.6667	Remote Similarity	NPD8150	Discontinued
0.6667	Remote Similarity	NPD7638	Approved
0.6667	Remote Similarity	NPD6765	Approved
0.6647	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6625	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6622	Remote Similarity	NPD1283	Approved
0.662	Remote Similarity	NPD7115	Discovery
0.66	Remote Similarity	NPD2861	Phase 2
0.6599	Remote Similarity	NPD1608	Approved
0.6594	Remote Similarity	NPD2182	Approved
0.6592	Remote Similarity	NPD8435	Approved
0.6591	Remote Similarity	NPD8312	Approved
0.6591	Remote Similarity	NPD8313	Approved
0.6588	Remote Similarity	NPD7229	Phase 3
0.6582	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6579	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6579	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6579	Remote Similarity	NPD6798	Discontinued
0.6571	Remote Similarity	NPD6912	Phase 3
0.6571	Remote Similarity	NPD7685	Pre-registration
0.6566	Remote Similarity	NPD7819	Suspended
0.6557	Remote Similarity	NPD8485	Approved
0.6552	Remote Similarity	NPD5585	Approved
0.6549	Remote Similarity	NPD4766	Approved
0.6533	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.6533	Remote Similarity	NPD5647	Approved
0.6533	Remote Similarity	NPD4624	Approved
0.6527	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6517	Remote Similarity	NPD6784	Approved
0.6517	Remote Similarity	NPD6785	Approved
0.6516	Remote Similarity	NPD6653	Approved
0.6513	Remote Similarity	NPD7095	Approved
0.6507	Remote Similarity	NPD1778	Approved
0.6494	Remote Similarity	NPD5844	Phase 1
0.6494	Remote Similarity	NPD2979	Phase 3
0.6494	Remote Similarity	NPD3620	Phase 2
0.6494	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6493	Remote Similarity	NPD7798	Approved
0.6488	Remote Similarity	NPD7768	Phase 2
0.6481	Remote Similarity	NPD2533	Approved
0.6481	Remote Similarity	NPD8389	Clinical (unspecified phase)
0.6481	Remote Similarity	NPD2532	Approved
0.6481	Remote Similarity	NPD2534	Approved
0.6471	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6467	Remote Similarity	NPD2797	Approved
0.6458	Remote Similarity	NPD4230	Clinical (unspecified phase)
0.6456	Remote Similarity	NPD2346	Discontinued
0.6453	Remote Similarity	NPD8051	Clinical (unspecified phase)
0.6452	Remote Similarity	NPD5124	Phase 1
0.6452	Remote Similarity	NPD8486	Clinical (unspecified phase)
0.6452	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6447	Remote Similarity	NPD4908	Phase 1
0.6441	Remote Similarity	NPD8658	Clinical (unspecified phase)
0.6439	Remote Similarity	NPD1693	Approved
0.6438	Remote Similarity	NPD3750	Approved
0.6436	Remote Similarity	NPD7497	Discontinued
0.6436	Remote Similarity	NPD7680	Approved
0.6429	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD7713	Phase 3
0.6429	Remote Similarity	NPD2067	Discontinued
0.6424	Remote Similarity	NPD3226	Approved
0.6419	Remote Similarity	NPD6287	Discontinued
0.6419	Remote Similarity	NPD4806	Approved
0.6419	Remote Similarity	NPD1281	Approved
0.6419	Remote Similarity	NPD4807	Approved
0.6418	Remote Similarity	NPD9495	Approved
0.6416	Remote Similarity	NPD7997	Clinical (unspecified phase)
0.6412	Remote Similarity	NPD1088	Approved
0.6412	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.6409	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.64	Remote Similarity	NPD8651	Approved
0.6398	Remote Similarity	NPD7237	Clinical (unspecified phase)
0.6398	Remote Similarity	NPD6190	Approved
0.6398	Remote Similarity	NPD7274	Clinical (unspecified phase)
0.6395	Remote Similarity	NPD17	Approved
0.6395	Remote Similarity	NPD5305	Approved
0.6395	Remote Similarity	NPD5306	Approved
0.6395	Remote Similarity	NPD7315	Approved
0.6395	Remote Similarity	NPD7725	Approved
0.6395	Remote Similarity	NPD4059	Approved
0.6392	Remote Similarity	NPD5406	Approved
0.6392	Remote Similarity	NPD2438	Suspended
0.6392	Remote Similarity	NPD5404	Approved
0.6392	Remote Similarity	NPD5405	Approved
0.6392	Remote Similarity	NPD5408	Approved
0.6391	Remote Similarity	NPD1989	Approved
0.6387	Remote Similarity	NPD4060	Phase 1
0.6382	Remote Similarity	NPD3664	Approved
0.6382	Remote Similarity	NPD3661	Approved
0.6382	Remote Similarity	NPD3662	Phase 3
0.6382	Remote Similarity	NPD3663	Approved
0.637	Remote Similarity	NPD9545	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