NPASS Compound

Structure

NPC471863 OpenBabel07101719402D 44 51 0 0 1 0 0 0 0 0999 V2000 -4.0668 -4.9324 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 -3.5926 -0.8544 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 -2.6819 -3.8110 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 -1.0182 -3.1723 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 -2.3455 -5.3936 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 -3.0886 -4.7245 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 -1.6874 -3.9155 0.0000 C 0 0 0 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 0 0 0 0 0 0 0 0 0 0 -2.3054 -2.0134 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 1.7321 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.9745 -2.7565 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.6144 -1.0623 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.4794 -4.8936 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 1 24 1 0 0 0 0 4 37 1 0 0 0 0 5 42 1 0 0 0 0 6 7 2 0 0 0 0 6 8 1 0 0 0 0 7 9 1 0 0 0 0 8 10 2 0 0 0 0 9 25 2 0 0 0 0 10 25 1 0 0 0 0 11 14 1 0 0 0 0 11 26 2 0 0 0 0 12 16 1 0 0 0 0 12 29 1 0 0 0 0 13 15 2 0 0 0 0 13 31 1 0 0 0 0 14 35 1 0 0 0 0 15 38 1 0 0 0 0 17 24 1 0 0 0 0 17 27 2 0 0 0 0 18 26 1 0 0 0 0 18 30 1 0 0 0 0 19 27 1 0 0 0 0 20 32 1 0 0 0 0 20 33 1 0 0 0 0 21 24 2 0 0 0 0 21 43 1 0 0 0 0 22 38 1 0 0 0 0 22 39 1 0 0 0 0 23 36 1 0 0 0 0 23 44 1 0 0 0 0 26 36 1 0 0 0 0 27 43 1 0 0 0 0 28 19 1 6 0 0 0 28 29 1 0 0 0 0 28 34 1 0 0 0 0 29 38 1 1 0 0 0 30 25 1 6 0 0 0 30 44 1 0 0 0 0 31 35 1 1 0 0 0 31 37 1 0 0 0 0 32 35 1 1 0 0 0 32 36 1 0 0 0 0 33 37 1 0 0 0 0 33 40 2 0 0 0 0 34 41 2 0 0 0 0 34 42 1 0 0 0 0 35 2 1 1 0 0 0 36 3 1 6 0 0 0 37 39 1 6 0 0 0 38 39 1 6 0 0 0 39 16 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	594.33
Volume:	634.871
LogP:	6.051
LogD:	4.621
LogS:	-5.639
# Rotatable Bonds:	6
TPSA:	65.74
# H-Bond Aceptor:	5
# H-Bond Donor:	0
# Rings:	8
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.259
Synthetic Accessibility Score:	5.662
Fsp3:	0.59
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Rejected
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:	-5.116
MDCK Permeability:	2.5165605620713905e-05
Pgp-inhibitor:	0.996
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.002
20% Bioavailability (F20%):	0.347
30% Bioavailability (F30%):	0.989

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.725
Plasma Protein Binding (PPB):	93.2148666381836%
Volume Distribution (VD):	2.019
Pgp-substrate:	5.618695259094238%

ADMET: Metabolism

CYP1A2-inhibitor:	0.034
CYP1A2-substrate:	0.706
CYP2C19-inhibitor:	0.68
CYP2C19-substrate:	0.914
CYP2C9-inhibitor:	0.871
CYP2C9-substrate:	0.127
CYP2D6-inhibitor:	0.513
CYP2D6-substrate:	0.218
CYP3A4-inhibitor:	0.976
CYP3A4-substrate:	0.914

ADMET: Excretion

Clearance (CL):	11.508
Half-life (T1/2):	0.113

ADMET: Toxicity

hERG Blockers:	0.934
Human Hepatotoxicity (H-HT):	0.409
Drug-inuced Liver Injury (DILI):	0.074
AMES Toxicity:	0.009
Rat Oral Acute Toxicity:	0.954
Maximum Recommended Daily Dose:	0.911
Skin Sensitization:	0.093
Carcinogencity:	0.197
Eye Corrosion:	0.003
Eye Irritation:	0.01
Respiratory Toxicity:	0.973

Download Data

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

Natural Product: NPC471863

Natural Product ID:	NPC471863
*Common Name:**	DATWCOKIVWRIME-BQWBNKKYSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	DATWCOKIVWRIME-BQWBNKKYSA-N
Standard InCHI:	InChI=1S/C39H46O5/c1-24-17-27(43-21-24)19-28(34(41)42-5)29-12-16-39-22-38(29,39)15-13-31-35(2)14-11-26-18-30(25-9-7-6-8-10-25)44-23-36(26,3)32(35)20-33(40)37(31,39)4/h6-11,13,15,17,21,28-32H,12,14,16,18-20,22-23H2,1-5H3/t28-,29-,30-,31+,32+,35+,36-,37-,38+,39+/m0/s1
SMILES:	CC1=COC(=C1)CC(C2CCC34C2(C3)C=CC5C4(C(=O)CC6C5(CC=C7C6(COC(C7)C8=CC=CC=C8)C)C)C)C(=O)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3261941
PubChem CID:	90676177
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001194] Oxosteroids

*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
EC50	1
IC50	5
Others	1

Activity Type	# Activity
Cell Line	5
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT116	Cell Line	HL-60	Homo sapiens	IC50	=	10200.0	nM	PMID[560210]
NPT659	Cell Line	SMMC-7721	Homo sapiens	IC50	=	24800.0	nM	PMID[560210]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	17600.0	nM	PMID[560210]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	21000.0	nM	PMID[560210]
NPT660	Cell Line	SW480	Homo sapiens	IC50	>	40000.0	nM	PMID[560210]
NPT2779	Organism	Spodoptera exigua	Spodoptera exigua	EC50	>	100.0	microg/cm2	PMID[560210]
NPT1272	Organism	Panagrellus redivivus	Panagrellus redivivus	mortality	=	2.5	%	PMID[560210]

☑ 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 NPC471863 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	412
0.1-0.2	1549
0.2-0.3	2770
0.3-0.4	6601
0.4-0.5	13153
0.5-0.6	9164
0.6-0.7	7992
0.7-0.8	976
0.8-0.85	74
0.85-0.9	5
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.902	High Similarity	NPC25351
0.88	High Similarity	NPC56731
0.8627	High Similarity	NPC93666
0.8618	High Similarity	NPC471292
0.8616	High Similarity	NPC471003
0.8545	High Similarity	NPC167340
0.8543	High Similarity	NPC470273
0.8487	Intermediate Similarity	NPC199044
0.8487	Intermediate Similarity	NPC238843
0.8467	Intermediate Similarity	NPC56197
0.8415	Intermediate Similarity	NPC302392
0.8366	Intermediate Similarity	NPC142113
0.8333	Intermediate Similarity	NPC220094
0.8333	Intermediate Similarity	NPC476943
0.8323	Intermediate Similarity	NPC224418
0.8312	Intermediate Similarity	NPC247221
0.8291	Intermediate Similarity	NPC246164
0.8267	Intermediate Similarity	NPC310830
0.8267	Intermediate Similarity	NPC307401
0.8261	Intermediate Similarity	NPC84349
0.8243	Intermediate Similarity	NPC471006
0.8217	Intermediate Similarity	NPC95526
0.8205	Intermediate Similarity	NPC71821
0.82	Intermediate Similarity	NPC146872
0.8165	Intermediate Similarity	NPC470997
0.8158	Intermediate Similarity	NPC202260
0.8148	Intermediate Similarity	NPC474932
0.8146	Intermediate Similarity	NPC42400
0.8141	Intermediate Similarity	NPC233763
0.8138	Intermediate Similarity	NPC74612
0.8137	Intermediate Similarity	NPC104736
0.8137	Intermediate Similarity	NPC41880
0.8133	Intermediate Similarity	NPC92941
0.8121	Intermediate Similarity	NPC470740
0.8113	Intermediate Similarity	NPC272590
0.8108	Intermediate Similarity	NPC298190
0.8101	Intermediate Similarity	NPC471001
0.8101	Intermediate Similarity	NPC234494
0.8101	Intermediate Similarity	NPC329180
0.8101	Intermediate Similarity	NPC253591
0.8092	Intermediate Similarity	NPC236532
0.8089	Intermediate Similarity	NPC10088
0.8089	Intermediate Similarity	NPC471174
0.8086	Intermediate Similarity	NPC304692
0.8086	Intermediate Similarity	NPC7059
0.8077	Intermediate Similarity	NPC185456
0.8075	Intermediate Similarity	NPC469850
0.8072	Intermediate Similarity	NPC473766
0.8072	Intermediate Similarity	NPC473753
0.8072	Intermediate Similarity	NPC310572
0.8069	Intermediate Similarity	NPC179354
0.8065	Intermediate Similarity	NPC267632
0.8063	Intermediate Similarity	NPC33938
0.8061	Intermediate Similarity	NPC27541
0.8061	Intermediate Similarity	NPC62692
0.8061	Intermediate Similarity	NPC261184
0.8061	Intermediate Similarity	NPC61967
0.8061	Intermediate Similarity	NPC126984
0.805	Intermediate Similarity	NPC159927
0.805	Intermediate Similarity	NPC212257
0.805	Intermediate Similarity	NPC46551
0.805	Intermediate Similarity	NPC469335
0.8049	Intermediate Similarity	NPC197596
0.8037	Intermediate Similarity	NPC474611
0.8037	Intermediate Similarity	NPC473368
0.8026	Intermediate Similarity	NPC470742
0.8025	Intermediate Similarity	NPC62799
0.8012	Intermediate Similarity	NPC44606
0.8012	Intermediate Similarity	NPC277618
0.8	Intermediate Similarity	NPC261659
0.8	Intermediate Similarity	NPC475039
0.8	Intermediate Similarity	NPC144010
0.8	Intermediate Similarity	NPC476035
0.8	Intermediate Similarity	NPC14499
0.7988	Intermediate Similarity	NPC8389
0.7987	Intermediate Similarity	NPC470278
0.7987	Intermediate Similarity	NPC148374
0.7976	Intermediate Similarity	NPC472660
0.7975	Intermediate Similarity	NPC216755
0.7975	Intermediate Similarity	NPC469847
0.7973	Intermediate Similarity	NPC59502
0.7973	Intermediate Similarity	NPC208389
0.7963	Intermediate Similarity	NPC92979
0.7962	Intermediate Similarity	NPC114513
0.7962	Intermediate Similarity	NPC290038
0.7962	Intermediate Similarity	NPC245522
0.7952	Intermediate Similarity	NPC276735
0.7952	Intermediate Similarity	NPC472664
0.795	Intermediate Similarity	NPC294511
0.795	Intermediate Similarity	NPC121615
0.7939	Intermediate Similarity	NPC68848
0.7939	Intermediate Similarity	NPC79571
0.7937	Intermediate Similarity	NPC477404
0.7937	Intermediate Similarity	NPC156189
0.7937	Intermediate Similarity	NPC196864
0.7935	Intermediate Similarity	NPC205765
0.7933	Intermediate Similarity	NPC471817
0.7931	Intermediate Similarity	NPC16922
0.7929	Intermediate Similarity	NPC475237
0.7929	Intermediate Similarity	NPC475641
0.7925	Intermediate Similarity	NPC19747
0.7922	Intermediate Similarity	NPC90953
0.7922	Intermediate Similarity	NPC474722
0.7917	Intermediate Similarity	NPC296558
0.7914	Intermediate Similarity	NPC209364
0.7911	Intermediate Similarity	NPC470999
0.7911	Intermediate Similarity	NPC346
0.7911	Intermediate Similarity	NPC276676
0.7911	Intermediate Similarity	NPC262198
0.7908	Intermediate Similarity	NPC170604
0.7908	Intermediate Similarity	NPC215109
0.7904	Intermediate Similarity	NPC475779
0.7901	Intermediate Similarity	NPC178932
0.7901	Intermediate Similarity	NPC10429
0.7898	Intermediate Similarity	NPC476944
0.7892	Intermediate Similarity	NPC285567
0.7892	Intermediate Similarity	NPC283209
0.7881	Intermediate Similarity	NPC293253
0.7879	Intermediate Similarity	NPC472299
0.7879	Intermediate Similarity	NPC287559
0.7875	Intermediate Similarity	NPC470791
0.7875	Intermediate Similarity	NPC470998
0.7875	Intermediate Similarity	NPC472654
0.7875	Intermediate Similarity	NPC470790
0.787	Intermediate Similarity	NPC118086
0.787	Intermediate Similarity	NPC88593
0.7867	Intermediate Similarity	NPC475092
0.7866	Intermediate Similarity	NPC472283
0.7866	Intermediate Similarity	NPC194499
0.7866	Intermediate Similarity	NPC195954
0.7866	Intermediate Similarity	NPC286722
0.7866	Intermediate Similarity	NPC88007
0.7862	Intermediate Similarity	NPC250228
0.7862	Intermediate Similarity	NPC302987
0.7853	Intermediate Similarity	NPC469336
0.7853	Intermediate Similarity	NPC141538
0.7853	Intermediate Similarity	NPC296807
0.7853	Intermediate Similarity	NPC281258
0.7853	Intermediate Similarity	NPC155939
0.7848	Intermediate Similarity	NPC34056
0.784	Intermediate Similarity	NPC469503
0.784	Intermediate Similarity	NPC471002
0.7838	Intermediate Similarity	NPC83178
0.7834	Intermediate Similarity	NPC80635
0.7834	Intermediate Similarity	NPC470741
0.7826	Intermediate Similarity	NPC472298
0.7826	Intermediate Similarity	NPC228842
0.7826	Intermediate Similarity	NPC476122
0.7824	Intermediate Similarity	NPC294512
0.7823	Intermediate Similarity	NPC473885
0.7823	Intermediate Similarity	NPC471074
0.7818	Intermediate Similarity	NPC116639
0.7818	Intermediate Similarity	NPC475295
0.7818	Intermediate Similarity	NPC473473
0.7805	Intermediate Similarity	NPC107646
0.7805	Intermediate Similarity	NPC60973
0.7793	Intermediate Similarity	NPC97566
0.7792	Intermediate Similarity	NPC310043
0.7791	Intermediate Similarity	NPC176413
0.7791	Intermediate Similarity	NPC56953
0.7791	Intermediate Similarity	NPC30222
0.7785	Intermediate Similarity	NPC84479
0.7785	Intermediate Similarity	NPC251865
0.7785	Intermediate Similarity	NPC476917
0.7785	Intermediate Similarity	NPC112706
0.7785	Intermediate Similarity	NPC327527
0.7785	Intermediate Similarity	NPC207294
0.7784	Intermediate Similarity	NPC165218
0.7784	Intermediate Similarity	NPC472669
0.7784	Intermediate Similarity	NPC224394
0.7784	Intermediate Similarity	NPC663
0.7778	Intermediate Similarity	NPC116717
0.7778	Intermediate Similarity	NPC471000
0.7771	Intermediate Similarity	NPC263337
0.7771	Intermediate Similarity	NPC333139
0.7771	Intermediate Similarity	NPC473152
0.7771	Intermediate Similarity	NPC121158
0.777	Intermediate Similarity	NPC138139
0.777	Intermediate Similarity	NPC46536
0.7765	Intermediate Similarity	NPC471859
0.7765	Intermediate Similarity	NPC471860
0.7764	Intermediate Similarity	NPC211625
0.7764	Intermediate Similarity	NPC192069
0.7758	Intermediate Similarity	NPC81405
0.7756	Intermediate Similarity	NPC471862
0.7755	Intermediate Similarity	NPC83115
0.7755	Intermediate Similarity	NPC188377
0.7755	Intermediate Similarity	NPC65735
0.775	Intermediate Similarity	NPC470941
0.775	Intermediate Similarity	NPC281398
0.775	Intermediate Similarity	NPC221809
0.7748	Intermediate Similarity	NPC89133
0.7744	Intermediate Similarity	NPC476262
0.7744	Intermediate Similarity	NPC35000
0.774	Intermediate Similarity	NPC36255
0.7733	Intermediate Similarity	NPC198904
0.773	Intermediate Similarity	NPC472672
0.773	Intermediate Similarity	NPC470996
0.773	Intermediate Similarity	NPC476201
0.773	Intermediate Similarity	NPC48671

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 NPC471863 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	343
0.1-0.2	907
0.2-0.3	1378
0.3-0.4	2697
0.4-0.5	2408
0.5-0.6	1119
0.6-0.7	281
0.7-0.8	17
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
0.7922	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7771	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.775	Intermediate Similarity	NPD6273	Approved
0.767	Intermediate Similarity	NPD8434	Phase 2
0.7586	Intermediate Similarity	NPD6765	Approved
0.7586	Intermediate Similarity	NPD6764	Approved
0.7582	Intermediate Similarity	NPD8032	Phase 2
0.753	Intermediate Similarity	NPD5761	Phase 2
0.753	Intermediate Similarity	NPD5760	Phase 2
0.7467	Intermediate Similarity	NPD1876	Approved
0.7416	Intermediate Similarity	NPD6784	Approved
0.7416	Intermediate Similarity	NPD6785	Approved
0.7358	Intermediate Similarity	NPD2346	Discontinued
0.7358	Intermediate Similarity	NPD1471	Phase 3
0.7329	Intermediate Similarity	NPD4628	Phase 3
0.7315	Intermediate Similarity	NPD7457	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD5585	Approved
0.7289	Intermediate Similarity	NPD7458	Discontinued
0.7267	Intermediate Similarity	NPD8127	Discontinued
0.7248	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.7239	Intermediate Similarity	NPD7236	Approved
0.7233	Intermediate Similarity	NPD2799	Discontinued
0.7222	Intermediate Similarity	NPD7003	Approved
0.7219	Intermediate Similarity	NPD3972	Approved
0.7186	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD2313	Discontinued
0.7169	Intermediate Similarity	NPD920	Approved
0.7161	Intermediate Similarity	NPD6832	Phase 2
0.7159	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7125	Intermediate Similarity	NPD3748	Approved
0.7118	Intermediate Similarity	NPD7819	Suspended
0.7083	Intermediate Similarity	NPD3226	Approved
0.7078	Intermediate Similarity	NPD3266	Approved
0.7078	Intermediate Similarity	NPD3267	Approved
0.7076	Intermediate Similarity	NPD5616	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD4359	Approved
0.7055	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7044	Intermediate Similarity	NPD6355	Discontinued
0.7041	Intermediate Similarity	NPD7028	Phase 2
0.7037	Intermediate Similarity	NPD2344	Approved
0.7024	Intermediate Similarity	NPD7239	Suspended
0.7012	Intermediate Similarity	NPD8166	Discontinued
0.7011	Intermediate Similarity	NPD5494	Approved
0.6981	Remote Similarity	NPD4140	Approved
0.6981	Remote Similarity	NPD2979	Phase 3
0.6981	Remote Similarity	NPD4307	Phase 2
0.6962	Remote Similarity	NPD3268	Approved
0.6957	Remote Similarity	NPD7097	Phase 1
0.6948	Remote Similarity	NPD5327	Phase 3
0.694	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6937	Remote Similarity	NPD4622	Approved
0.6937	Remote Similarity	NPD4618	Approved
0.6932	Remote Similarity	NPD6808	Phase 2
0.6928	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD8312	Approved
0.6923	Remote Similarity	NPD8313	Approved
0.6923	Remote Similarity	NPD2798	Approved
0.6919	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD4870	Approved
0.6909	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6909	Remote Similarity	NPD3750	Approved
0.6908	Remote Similarity	NPD17	Approved
0.6899	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD3749	Approved
0.6892	Remote Similarity	NPD1241	Discontinued
0.6879	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6871	Remote Similarity	NPD2796	Approved
0.6867	Remote Similarity	NPD3887	Approved
0.6867	Remote Similarity	NPD2309	Approved
0.6859	Remote Similarity	NPD2797	Approved
0.6852	Remote Similarity	NPD5689	Approved
0.6852	Remote Similarity	NPD5688	Approved
0.6842	Remote Similarity	NPD6599	Discontinued
0.6832	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD6005	Phase 3
0.6829	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD6004	Phase 3
0.6829	Remote Similarity	NPD6002	Phase 3
0.6824	Remote Similarity	NPD6858	Approved
0.6824	Remote Similarity	NPD7094	Approved
0.6818	Remote Similarity	NPD1281	Approved
0.6813	Remote Similarity	NPD6559	Discontinued
0.6813	Remote Similarity	NPD7685	Pre-registration
0.6813	Remote Similarity	NPD6663	Approved
0.6813	Remote Similarity	NPD7961	Discontinued
0.681	Remote Similarity	NPD4308	Phase 3
0.6807	Remote Similarity	NPD4110	Phase 3
0.6807	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6802	Remote Similarity	NPD7411	Suspended
0.68	Remote Similarity	NPD7075	Discontinued
0.6781	Remote Similarity	NPD2182	Approved
0.6774	Remote Similarity	NPD1608	Approved
0.6768	Remote Similarity	NPD2438	Suspended
0.6763	Remote Similarity	NPD6280	Approved
0.6763	Remote Similarity	NPD6279	Approved
0.676	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.675	Remote Similarity	NPD3764	Approved
0.6747	Remote Similarity	NPD1243	Approved
0.6743	Remote Similarity	NPD7768	Phase 2
0.674	Remote Similarity	NPD5844	Phase 1
0.6738	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6728	Remote Similarity	NPD1933	Approved
0.6727	Remote Similarity	NPD5762	Approved
0.6727	Remote Similarity	NPD5763	Approved
0.6709	Remote Similarity	NPD5647	Approved
0.6709	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6705	Remote Similarity	NPD5890	Approved
0.6705	Remote Similarity	NPD5889	Approved
0.6688	Remote Similarity	NPD1283	Approved
0.6687	Remote Similarity	NPD7008	Discontinued
0.6687	Remote Similarity	NPD2897	Discontinued
0.6687	Remote Similarity	NPD6353	Approved
0.6685	Remote Similarity	NPD7799	Discontinued
0.6684	Remote Similarity	NPD4107	Approved
0.6683	Remote Similarity	NPD8404	Phase 2
0.6667	Remote Similarity	NPD1551	Phase 2
0.6667	Remote Similarity	NPD5736	Approved
0.6667	Remote Similarity	NPD2935	Discontinued
0.6667	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD919	Approved
0.6667	Remote Similarity	NPD6844	Discontinued
0.6667	Remote Similarity	NPD2531	Phase 2
0.6648	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6648	Remote Similarity	NPD7057	Phase 3
0.6648	Remote Similarity	NPD7058	Phase 2
0.6646	Remote Similarity	NPD6798	Discontinued
0.6646	Remote Similarity	NPD1049	Clinical (unspecified phase)
0.6646	Remote Similarity	NPD6362	Approved
0.6644	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.6632	Remote Similarity	NPD8285	Discontinued
0.6631	Remote Similarity	NPD8150	Discontinued
0.6629	Remote Similarity	NPD8455	Phase 2
0.6627	Remote Similarity	NPD2353	Approved
0.6627	Remote Similarity	NPD7440	Discontinued
0.6627	Remote Similarity	NPD7702	Clinical (unspecified phase)
0.6627	Remote Similarity	NPD2355	Clinical (unspecified phase)
0.6626	Remote Similarity	NPD5735	Approved
0.6623	Remote Similarity	NPD1651	Approved
0.6609	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6606	Remote Similarity	NPD7033	Discontinued
0.6605	Remote Similarity	NPD6233	Phase 2
0.6604	Remote Similarity	NPD1019	Discontinued
0.6603	Remote Similarity	NPD6287	Discontinued
0.66	Remote Similarity	NPD5535	Approved
0.6592	Remote Similarity	NPD6959	Discontinued
0.6591	Remote Similarity	NPD5402	Approved
0.6591	Remote Similarity	NPD5978	Approved
0.6591	Remote Similarity	NPD5977	Approved
0.6588	Remote Similarity	NPD6799	Approved
0.6587	Remote Similarity	NPD1549	Phase 2
0.6585	Remote Similarity	NPD6653	Approved
0.6584	Remote Similarity	NPD7095	Approved
0.6582	Remote Similarity	NPD7497	Discontinued
0.6571	Remote Similarity	NPD6801	Discontinued
0.6571	Remote Similarity	NPD7577	Discontinued
0.657	Remote Similarity	NPD3869	Phase 3
0.657	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.657	Remote Similarity	NPD3873	Phase 3
0.657	Remote Similarity	NPD5403	Approved
0.6566	Remote Similarity	NPD4476	Approved
0.6566	Remote Similarity	NPD4477	Approved
0.6566	Remote Similarity	NPD6099	Approved
0.6566	Remote Similarity	NPD6100	Approved
0.6564	Remote Similarity	NPD3140	Approved
0.6564	Remote Similarity	NPD3142	Approved
0.6564	Remote Similarity	NPD4482	Phase 3
0.6557	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD6585	Discontinued
0.6552	Remote Similarity	NPD4380	Phase 2
0.655	Remote Similarity	NPD5401	Approved
0.655	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6543	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6541	Remote Similarity	NPD1203	Approved
0.6538	Remote Similarity	NPD7473	Discontinued
0.6534	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6527	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6527	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6517	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6517	Remote Similarity	NPD8005	Clinical (unspecified phase)
0.6516	Remote Similarity	NPD5691	Approved
0.6516	Remote Similarity	NPD3025	Approved
0.6516	Remote Similarity	NPD3024	Approved
0.6514	Remote Similarity	NPD6677	Suspended
0.6514	Remote Similarity	NPD6873	Phase 2
0.6507	Remote Similarity	NPD164	Approved
0.6503	Remote Similarity	NPD7713	Phase 3
0.6503	Remote Similarity	NPD7228	Approved
0.6503	Remote Similarity	NPD7177	Discontinued
0.65	Remote Similarity	NPD1247	Approved
0.65	Remote Similarity	NPD7199	Phase 2
0.6497	Remote Similarity	NPD1611	Approved
0.6491	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6488	Remote Similarity	NPD5958	Discontinued
0.6488	Remote Similarity	NPD4534	Discontinued
0.6486	Remote Similarity	NPD7993	Clinical (unspecified phase)

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