NPASS Compound

Structure

CID185456 OpenBabel06191715562D 30 34 0 0 1 0 0 0 0 0999 V2000 -5.0791 -0.9540 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0792 -1.9608 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6521 -1.9615 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8721 -0.5035 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6826 1.0067 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8416 -1.4577 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3652 -2.9146 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6055 0.3010 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.9718 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5239 -2.4292 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1764 -0.4841 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.9422 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3657 -0.0004 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6827 -0.9700 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6824 0.0008 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8410 1.4566 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6826 -0.9721 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.3657 -0.9721 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8410 0.4856 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2067 -2.4288 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5241 0.4855 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8416 0.4859 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.2070 -1.4575 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5242 -1.4580 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 -1.6826 -0.0003 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7069 1.9569 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.0726 -2.9290 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5241 1.4855 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6060 -1.2697 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 23 1 0 0 0 0 2 23 1 0 0 0 0 6 9 1 0 0 0 0 6 17 1 0 0 0 0 7 10 2 0 0 0 0 7 20 1 0 0 0 0 8 11 2 0 0 0 0 8 15 1 0 0 0 0 9 25 1 0 0 0 0 10 24 1 0 0 0 0 11 30 1 0 0 0 0 12 16 1 0 0 0 0 12 19 2 0 0 0 0 13 18 1 0 0 0 0 13 21 1 0 0 0 0 14 15 2 0 0 0 0 14 30 1 0 0 0 0 15 22 1 0 0 0 0 16 22 1 0 0 0 0 16 27 2 0 0 0 0 17 24 1 6 0 0 0 17 26 1 0 0 0 0 18 23 1 0 0 0 0 18 24 1 6 0 0 0 19 25 1 0 0 0 0 19 26 1 0 0 0 0 20 23 1 0 0 0 0 20 28 2 0 0 0 0 21 26 1 1 0 0 0 21 29 1 0 0 0 0 22 25 1 1 0 0 0 24 3 1 6 0 0 0 25 4 1 1 0 0 0 26 5 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	408.23
Volume:	434.812
LogP:	3.273
LogD:	2.795
LogS:	-4.626
# Rotatable Bonds:	1
TPSA:	67.51
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	5
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.721
Synthetic Accessibility Score:	5.001
Fsp3:	0.615
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.247
MDCK Permeability:	4.208796235616319e-05
Pgp-inhibitor:	0.991
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.39
30% Bioavailability (F30%):	0.594

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.085
Plasma Protein Binding (PPB):	93.98404693603516%
Volume Distribution (VD):	1.707
Pgp-substrate:	7.178111553192139%

ADMET: Metabolism

CYP1A2-inhibitor:	0.021
CYP1A2-substrate:	0.524
CYP2C19-inhibitor:	0.168
CYP2C19-substrate:	0.843
CYP2C9-inhibitor:	0.463
CYP2C9-substrate:	0.073
CYP2D6-inhibitor:	0.059
CYP2D6-substrate:	0.042
CYP3A4-inhibitor:	0.9
CYP3A4-substrate:	0.872

ADMET: Excretion

Clearance (CL):	7.699
Half-life (T1/2):	0.358

ADMET: Toxicity

hERG Blockers:	0.036
Human Hepatotoxicity (H-HT):	0.393
Drug-inuced Liver Injury (DILI):	0.074
AMES Toxicity:	0.008
Rat Oral Acute Toxicity:	0.98
Maximum Recommended Daily Dose:	0.981
Skin Sensitization:	0.571
Carcinogencity:	0.143
Eye Corrosion:	0.004
Eye Irritation:	0.073
Respiratory Toxicity:	0.978

Download Data

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

Natural Product: NPC185456

Natural Product ID:	NPC185456
*Common Name:**	Nimbocinol
IUPAC Name:	(5R,7R,8R,9R,10R,13S,17R)-17-(furan-3-yl)-7-hydroxy-4,4,8,10,13-pentamethyl-6,7,9,11,12,17-hexahydro-5H-cyclopenta[a]phenanthrene-3,16-dione
Synonyms:	Nimbocinol
Standard InCHIKey:	BAMHPKTZTBFUOH-WWBRISJOSA-N
Standard InCHI:	InChI=1S/C26H32O4/c1-23(2)18-13-21(29)26(5)17(24(18,3)10-7-20(23)28)6-9-25(4)19(26)12-16(27)22(25)15-8-11-30-14-15/h7-8,10-12,14,17-18,21-22,29H,6,9,13H2,1-5H3/t17-,18+,21-,22-,24-,25-,26-/m1/s1
SMILES:	CC1(C)[C@@H]2C[C@H]([C@]3(C)[C@H](CC[C@]4(C)C3=CC(=O)[C@H]4c3ccoc3)[C@@]2(C)C=CC1=O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1774401
PubChem CID:	13875741
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
NPO4406	Azadirachta indica	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12193038]
NPO18932	Melia azedarach	Species	Meliaceae	Eukaryota	n.a.	Brazilian	n.a.	PMID[15387656]
NPO4406	Azadirachta indica	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[1593280]
NPO18932	Melia azedarach	Species	Meliaceae	Eukaryota	n.a.	ripe fruit	n.a.	PMID[16205005]
NPO4406	Azadirachta indica	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18816111]
NPO4406	Azadirachta indica	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19299148]
NPO4406	Azadirachta indica	Species	Meliaceae	Eukaryota	fruits	n.a.	n.a.	PMID[20669933]
NPO4406	Azadirachta indica	Species	Meliaceae	Eukaryota	Seeds	n.a.	n.a.	PMID[21381696]
NPO4406	Azadirachta indica	Species	Meliaceae	Eukaryota	n.a.	seed	n.a.	PMID[21381696]
NPO4406	Azadirachta indica	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[2607354]
NPO4406	Azadirachta indica	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[2614419]
NPO4406	Azadirachta indica	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26339153]
NPO4406	Azadirachta indica	Species	Meliaceae	Eukaryota	Leaves	n.a.	n.a.	PMID[28493718]
NPO18932	Melia azedarach	Species	Meliaceae	Eukaryota	Fruits	n.a.	n.a.	PMID[33253570]
NPO18932	Melia azedarach	Species	Meliaceae	Eukaryota	Seeds	n.a.	n.a.	PMID[3701342]
NPO4406	Azadirachta indica	Species	Meliaceae	Eukaryota	n.a.	bark	n.a.	PMID[9134742]
NPO4406	Azadirachta indica	Species	Meliaceae	Eukaryota	n.a.	fruit	n.a.	PMID[9134742]
NPO4406	Azadirachta indica	Species	Meliaceae	Eukaryota	n.a.	leaf	n.a.	PMID[9134742]
NPO18932	Melia azedarach	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18932	Melia azedarach	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18932	Melia azedarach	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO18932	Melia azedarach	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO18932	Melia azedarach	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4406	Azadirachta indica	Species	Meliaceae	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
IC50	5

Activity Type	# Activity
Cell Line	3
NON-MOLECULAR	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT116	Cell Line	HL-60	Homo sapiens	IC50	>	20000.0	nM	PMID[479059]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	20000.0	nM	PMID[479059]
NPT134	Cell Line	SK-BR-3	Homo sapiens	IC50	>	20000.0	nM	PMID[479059]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	20000.0	nM	PMID[479059]

☑ 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 NPC185456 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	327
0.1-0.2	1368
0.2-0.3	2752
0.3-0.4	6174
0.4-0.5	11612
0.5-0.6	10516
0.6-0.7	8769
0.7-0.8	898
0.8-0.85	196
0.85-0.9	70
0.9-0.95	13
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9714	High Similarity	NPC302987
0.95	High Similarity	NPC238843
0.95	High Similarity	NPC199044
0.9444	High Similarity	NPC272590
0.9366	High Similarity	NPC471292
0.9306	High Similarity	NPC470998
0.9306	High Similarity	NPC234494
0.9301	High Similarity	NPC471174
0.9252	High Similarity	NPC92979
0.9247	High Similarity	NPC470996
0.9241	High Similarity	NPC196846
0.9241	High Similarity	NPC470997
0.9214	High Similarity	NPC56197
0.9167	High Similarity	NPC216755
0.9116	High Similarity	NPC33938
0.8993	High Similarity	NPC141538
0.8993	High Similarity	NPC155939
0.8993	High Similarity	NPC296807
0.8986	High Similarity	NPC246164
0.8966	High Similarity	NPC470999
0.8912	High Similarity	NPC472654
0.8889	High Similarity	NPC224394
0.8889	High Similarity	NPC663
0.8867	High Similarity	NPC25351
0.8841	High Similarity	NPC61788
0.8811	High Similarity	NPC67003
0.88	High Similarity	NPC178932
0.8784	High Similarity	NPC471001
0.8759	High Similarity	NPC243577
0.875	High Similarity	NPC205765
0.875	High Similarity	NPC197137
0.8742	High Similarity	NPC469336
0.8723	High Similarity	NPC476947
0.8716	High Similarity	NPC471007
0.8714	High Similarity	NPC218838
0.8714	High Similarity	NPC471006
0.869	High Similarity	NPC52412
0.8667	High Similarity	NPC471000
0.863	High Similarity	NPC267632
0.8571	High Similarity	NPC476944
0.8571	High Similarity	NPC251865
0.8562	High Similarity	NPC121158
0.8543	High Similarity	NPC291150
0.8543	High Similarity	NPC116717
0.8531	High Similarity	NPC46896
0.8514	High Similarity	NPC5676
0.8514	High Similarity	NPC34056
0.8506	High Similarity	NPC470118
0.8506	High Similarity	NPC472772
0.8506	High Similarity	NPC469847
0.8506	High Similarity	NPC304692
0.8503	High Similarity	NPC476946
0.8497	Intermediate Similarity	NPC35000
0.8487	Intermediate Similarity	NPC471002
0.8487	Intermediate Similarity	NPC75906
0.8487	Intermediate Similarity	NPC472672
0.8487	Intermediate Similarity	NPC469503
0.8478	Intermediate Similarity	NPC23086
0.8477	Intermediate Similarity	NPC156189
0.8477	Intermediate Similarity	NPC469335
0.8477	Intermediate Similarity	NPC159927
0.8477	Intermediate Similarity	NPC5180
0.8472	Intermediate Similarity	NPC4764
0.8467	Intermediate Similarity	NPC93666
0.8462	Intermediate Similarity	NPC197596
0.8462	Intermediate Similarity	NPC470792
0.8462	Intermediate Similarity	NPC69028
0.8462	Intermediate Similarity	NPC158525
0.8456	Intermediate Similarity	NPC346
0.8446	Intermediate Similarity	NPC142113
0.8442	Intermediate Similarity	NPC104736
0.8442	Intermediate Similarity	NPC41880
0.8435	Intermediate Similarity	NPC263337
0.8431	Intermediate Similarity	NPC302054
0.8431	Intermediate Similarity	NPC253201
0.8431	Intermediate Similarity	NPC34421
0.8431	Intermediate Similarity	NPC237259
0.8431	Intermediate Similarity	NPC98206
0.8431	Intermediate Similarity	NPC30222
0.8414	Intermediate Similarity	NPC471996
0.8411	Intermediate Similarity	NPC195325
0.838	Intermediate Similarity	NPC471995
0.8378	Intermediate Similarity	NPC103134
0.8377	Intermediate Similarity	NPC264943
0.8377	Intermediate Similarity	NPC281258
0.8377	Intermediate Similarity	NPC179170
0.8366	Intermediate Similarity	NPC121615
0.8366	Intermediate Similarity	NPC294511
0.8356	Intermediate Similarity	NPC202260
0.8356	Intermediate Similarity	NPC90953
0.8355	Intermediate Similarity	NPC477404
0.8355	Intermediate Similarity	NPC196864
0.8355	Intermediate Similarity	NPC212257
0.8354	Intermediate Similarity	NPC276551
0.8345	Intermediate Similarity	NPC42400
0.8344	Intermediate Similarity	NPC472771
0.8344	Intermediate Similarity	NPC472767
0.8333	Intermediate Similarity	NPC140952
0.8333	Intermediate Similarity	NPC262198
0.8333	Intermediate Similarity	NPC475226
0.8333	Intermediate Similarity	NPC472823
0.8333	Intermediate Similarity	NPC84349
0.8333	Intermediate Similarity	NPC233763
0.8323	Intermediate Similarity	NPC285227
0.8321	Intermediate Similarity	NPC477967
0.8312	Intermediate Similarity	NPC57998
0.831	Intermediate Similarity	NPC298190
0.831	Intermediate Similarity	NPC89133
0.8302	Intermediate Similarity	NPC470875
0.8301	Intermediate Similarity	NPC472787
0.8299	Intermediate Similarity	NPC90296
0.8299	Intermediate Similarity	NPC18904
0.8291	Intermediate Similarity	NPC472773
0.8291	Intermediate Similarity	NPC292389
0.8291	Intermediate Similarity	NPC469338
0.8291	Intermediate Similarity	NPC477405
0.8291	Intermediate Similarity	NPC283209
0.8291	Intermediate Similarity	NPC165218
0.8289	Intermediate Similarity	NPC470791
0.8289	Intermediate Similarity	NPC125182
0.8289	Intermediate Similarity	NPC69647
0.8289	Intermediate Similarity	NPC470790
0.8288	Intermediate Similarity	NPC236532
0.8288	Intermediate Similarity	NPC476943
0.828	Intermediate Similarity	NPC470789
0.828	Intermediate Similarity	NPC287559
0.828	Intermediate Similarity	NPC477402
0.8278	Intermediate Similarity	NPC224418
0.8278	Intermediate Similarity	NPC250228
0.8278	Intermediate Similarity	NPC255414
0.8276	Intermediate Similarity	NPC146872
0.8269	Intermediate Similarity	NPC81405
0.8269	Intermediate Similarity	NPC470119
0.8269	Intermediate Similarity	NPC214495
0.8269	Intermediate Similarity	NPC475066
0.8267	Intermediate Similarity	NPC56731
0.8261	Intermediate Similarity	NPC470995
0.8258	Intermediate Similarity	NPC469850
0.8258	Intermediate Similarity	NPC88958
0.8258	Intermediate Similarity	NPC472786
0.8252	Intermediate Similarity	NPC471817
0.825	Intermediate Similarity	NPC478179
0.825	Intermediate Similarity	NPC476850
0.825	Intermediate Similarity	NPC476861
0.8247	Intermediate Similarity	NPC145830
0.8239	Intermediate Similarity	NPC470940
0.8239	Intermediate Similarity	NPC476925
0.8239	Intermediate Similarity	NPC469849
0.8239	Intermediate Similarity	NPC476856
0.8239	Intermediate Similarity	NPC476858
0.8239	Intermediate Similarity	NPC123088
0.8239	Intermediate Similarity	NPC476857
0.8228	Intermediate Similarity	NPC263432
0.8228	Intermediate Similarity	NPC329938
0.8228	Intermediate Similarity	NPC5079
0.8228	Intermediate Similarity	NPC68848
0.8228	Intermediate Similarity	NPC18986
0.8228	Intermediate Similarity	NPC471003
0.8227	Intermediate Similarity	NPC112706
0.8227	Intermediate Similarity	NPC477123
0.8227	Intermediate Similarity	NPC477040
0.8227	Intermediate Similarity	NPC476917
0.8227	Intermediate Similarity	NPC477966
0.8227	Intermediate Similarity	NPC327527
0.8227	Intermediate Similarity	NPC207294
0.8219	Intermediate Similarity	NPC310830
0.8217	Intermediate Similarity	NPC474611
0.8217	Intermediate Similarity	NPC307383
0.8217	Intermediate Similarity	NPC477403
0.8217	Intermediate Similarity	NPC472671
0.8214	Intermediate Similarity	NPC46536
0.8214	Intermediate Similarity	NPC138139
0.8199	Intermediate Similarity	NPC471397
0.8194	Intermediate Similarity	NPC282445
0.8188	Intermediate Similarity	NPC473152
0.8188	Intermediate Similarity	NPC62103
0.8188	Intermediate Similarity	NPC20578
0.8187	Intermediate Similarity	NPC121995
0.8187	Intermediate Similarity	NPC475779
0.8187	Intermediate Similarity	NPC478178
0.8176	Intermediate Similarity	NPC419
0.8176	Intermediate Similarity	NPC51568
0.8176	Intermediate Similarity	NPC148374
0.8176	Intermediate Similarity	NPC234660
0.8176	Intermediate Similarity	NPC285567
0.8169	Intermediate Similarity	NPC198904
0.8169	Intermediate Similarity	NPC59502
0.8165	Intermediate Similarity	NPC25255
0.8163	Intermediate Similarity	NPC220094
0.8158	Intermediate Similarity	NPC71821
0.8156	Intermediate Similarity	NPC83178
0.8156	Intermediate Similarity	NPC290955
0.8153	Intermediate Similarity	NPC472777
0.8153	Intermediate Similarity	NPC472778
0.8153	Intermediate Similarity	NPC472776
0.8153	Intermediate Similarity	NPC472283
0.8153	Intermediate Similarity	NPC194499
0.8153	Intermediate Similarity	NPC249021
0.8146	Intermediate Similarity	NPC41182
0.8143	Intermediate Similarity	NPC303010

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 NPC185456 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	298
0.1-0.2	970
0.2-0.3	1770
0.3-0.4	2703
0.4-0.5	2094
0.5-0.6	1033
0.6-0.7	268
0.7-0.8	12
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8618	High Similarity	NPD5761	Phase 2
0.8618	High Similarity	NPD5760	Phase 2
0.7844	Intermediate Similarity	NPD6764	Approved
0.7844	Intermediate Similarity	NPD6765	Approved
0.7719	Intermediate Similarity	NPD8434	Phase 2
0.7661	Intermediate Similarity	NPD6785	Approved
0.7661	Intermediate Similarity	NPD6784	Approved
0.7632	Intermediate Similarity	NPD1471	Phase 3
0.7516	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD6273	Approved
0.729	Intermediate Similarity	NPD2344	Approved
0.7261	Intermediate Similarity	NPD4628	Phase 3
0.7197	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD7236	Approved
0.7107	Intermediate Similarity	NPD2309	Approved
0.7051	Intermediate Similarity	NPD2799	Discontinued
0.7047	Intermediate Similarity	NPD1876	Approved
0.7027	Intermediate Similarity	NPD3972	Approved
0.7012	Intermediate Similarity	NPD3226	Approved
0.7012	Intermediate Similarity	NPD7458	Discontinued
0.7006	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD8127	Discontinued
0.6962	Remote Similarity	NPD2346	Discontinued
0.6951	Remote Similarity	NPD7239	Suspended
0.6948	Remote Similarity	NPD8032	Phase 2
0.6946	Remote Similarity	NPD7819	Suspended
0.6939	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6909	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD5616	Clinical (unspecified phase)
0.6903	Remote Similarity	NPD4140	Approved
0.6897	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6883	Remote Similarity	NPD3268	Approved
0.6871	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD7028	Phase 2
0.6859	Remote Similarity	NPD5735	Approved
0.6832	Remote Similarity	NPD7003	Approved
0.6815	Remote Similarity	NPD6353	Approved
0.6792	Remote Similarity	NPD6099	Approved
0.6792	Remote Similarity	NPD6100	Approved
0.6792	Remote Similarity	NPD2796	Approved
0.6774	Remote Similarity	NPD2313	Discontinued
0.6763	Remote Similarity	NPD6808	Phase 2
0.6755	Remote Similarity	NPD5327	Phase 3
0.6752	Remote Similarity	NPD6355	Discontinued
0.6746	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6744	Remote Similarity	NPD5494	Approved
0.6742	Remote Similarity	NPD6559	Discontinued
0.6733	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6732	Remote Similarity	NPD2798	Approved
0.6728	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6726	Remote Similarity	NPD7411	Suspended
0.6708	Remote Similarity	NPD1549	Phase 2
0.669	Remote Similarity	NPD1241	Discontinued
0.6687	Remote Similarity	NPD920	Approved
0.6686	Remote Similarity	NPD6280	Approved
0.6686	Remote Similarity	NPD6279	Approved
0.6685	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD3266	Approved
0.6667	Remote Similarity	NPD7457	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6599	Discontinued
0.6667	Remote Similarity	NPD2800	Approved
0.6667	Remote Similarity	NPD3267	Approved
0.6647	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6646	Remote Similarity	NPD5763	Approved
0.6646	Remote Similarity	NPD5762	Approved
0.6646	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6646	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6628	Remote Similarity	NPD7075	Discontinued
0.6628	Remote Similarity	NPD3749	Approved
0.6626	Remote Similarity	NPD8166	Discontinued
0.6626	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6626	Remote Similarity	NPD3750	Approved
0.6626	Remote Similarity	NPD4110	Phase 3
0.6624	Remote Similarity	NPD6663	Approved
0.6616	Remote Similarity	NPD8404	Phase 2
0.6609	Remote Similarity	NPD1247	Approved
0.6608	Remote Similarity	NPD2296	Approved
0.66	Remote Similarity	NPD2932	Approved
0.6588	Remote Similarity	NPD6844	Discontinued
0.6579	Remote Similarity	NPD1608	Approved
0.6573	Remote Similarity	NPD5844	Phase 1
0.657	Remote Similarity	NPD7057	Phase 3
0.657	Remote Similarity	NPD7058	Phase 2
0.657	Remote Similarity	NPD3882	Suspended
0.6568	Remote Similarity	NPD4380	Phase 2
0.6566	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6558	Remote Similarity	NPD2797	Approved
0.6545	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6543	Remote Similarity	NPD6004	Phase 3
0.6543	Remote Similarity	NPD6002	Phase 3
0.6543	Remote Similarity	NPD6005	Phase 3
0.6543	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6543	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6538	Remote Similarity	NPD6832	Phase 2
0.6522	Remote Similarity	NPD1510	Phase 2
0.6522	Remote Similarity	NPD3748	Approved
0.6522	Remote Similarity	NPD4308	Phase 3
0.6517	Remote Similarity	NPD3818	Discontinued
0.6517	Remote Similarity	NPD7799	Discontinued
0.6514	Remote Similarity	NPD7199	Phase 2
0.6514	Remote Similarity	NPD6959	Discontinued
0.6509	Remote Similarity	NPD2651	Approved
0.6509	Remote Similarity	NPD2649	Approved
0.6503	Remote Similarity	NPD2424	Discontinued
0.6497	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6497	Remote Similarity	NPD4575	Clinical (unspecified phase)
0.6497	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6494	Remote Similarity	NPD1283	Approved
0.6491	Remote Similarity	NPD6801	Discontinued
0.6491	Remote Similarity	NPD1934	Approved
0.6491	Remote Similarity	NPD7577	Discontinued
0.649	Remote Similarity	NPD3019	Approved
0.6481	Remote Similarity	NPD2935	Discontinued
0.6474	Remote Similarity	NPD5736	Approved
0.6474	Remote Similarity	NPD9494	Approved
0.6467	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6467	Remote Similarity	NPD2533	Approved
0.6467	Remote Similarity	NPD2532	Approved
0.6467	Remote Similarity	NPD2534	Approved
0.6461	Remote Similarity	NPD7473	Discontinued
0.646	Remote Similarity	NPD7097	Phase 1
0.6458	Remote Similarity	NPD3057	Approved
0.6456	Remote Similarity	NPD6798	Discontinued
0.6456	Remote Similarity	NPD3764	Approved
0.6456	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6441	Remote Similarity	NPD3926	Phase 2
0.6438	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.6437	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6424	Remote Similarity	NPD1651	Approved
0.642	Remote Similarity	NPD7033	Discontinued
0.641	Remote Similarity	NPD5647	Approved
0.641	Remote Similarity	NPD4624	Approved
0.6407	Remote Similarity	NPD6799	Approved
0.6407	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.64	Remote Similarity	NPD919	Approved
0.6398	Remote Similarity	NPD1607	Approved
0.6393	Remote Similarity	NPD8312	Approved
0.6393	Remote Similarity	NPD8313	Approved
0.6392	Remote Similarity	NPD7095	Approved
0.6386	Remote Similarity	NPD3887	Approved
0.6384	Remote Similarity	NPD7229	Phase 3
0.6382	Remote Similarity	NPD1778	Approved
0.6382	Remote Similarity	NPD17	Approved
0.638	Remote Similarity	NPD1551	Phase 2
0.638	Remote Similarity	NPD4477	Approved
0.638	Remote Similarity	NPD4476	Approved
0.6379	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6379	Remote Similarity	NPD4967	Phase 2
0.6379	Remote Similarity	NPD4966	Approved
0.6379	Remote Similarity	NPD7768	Phase 2
0.6379	Remote Similarity	NPD4965	Approved
0.6376	Remote Similarity	NPD7157	Approved
0.6375	Remote Similarity	NPD1240	Approved
0.6375	Remote Similarity	NPD3140	Approved
0.6375	Remote Similarity	NPD3142	Approved
0.6375	Remote Similarity	NPD2979	Phase 3
0.6375	Remote Similarity	NPD4307	Phase 2
0.6373	Remote Similarity	NPD2972	Approved
0.6373	Remote Similarity	NPD3533	Approved
0.6373	Remote Similarity	NPD2491	Approved
0.6364	Remote Similarity	NPD1243	Approved
0.6358	Remote Similarity	NPD2801	Approved
0.6352	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6348	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6346	Remote Similarity	NPD1470	Approved
0.634	Remote Similarity	NPD3023	Approved
0.634	Remote Similarity	NPD3026	Approved
0.6339	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6333	Remote Similarity	NPD7177	Discontinued
0.6333	Remote Similarity	NPD2163	Approved
0.633	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6322	Remote Similarity	NPD5978	Approved
0.6322	Remote Similarity	NPD5977	Approved
0.6316	Remote Similarity	NPD3024	Approved
0.6316	Remote Similarity	NPD5585	Approved
0.6316	Remote Similarity	NPD3025	Approved
0.6313	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6313	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6313	Remote Similarity	NPD6166	Phase 2
0.6312	Remote Similarity	NPD7961	Discontinued
0.6306	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6303	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6301	Remote Similarity	NPD37	Approved
0.6299	Remote Similarity	NPD1281	Approved
0.6298	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6296	Remote Similarity	NPD6653	Approved
0.6296	Remote Similarity	NPD6651	Approved
0.6292	Remote Similarity	NPD6232	Discontinued
0.6291	Remote Similarity	NPD9092	Discovery
0.6289	Remote Similarity	NPD3448	Approved
0.6287	Remote Similarity	NPD2354	Approved
0.6284	Remote Similarity	NPD7685	Pre-registration
0.6282	Remote Similarity	NPD8651	Approved
0.628	Remote Similarity	NPD2438	Suspended
0.6273	Remote Similarity	NPD4060	Phase 1
0.6273	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6273	Remote Similarity	NPD3620	Phase 2
0.6272	Remote Similarity	NPD4661	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