NPASS Compound

Structure

NPC120239 OpenBabel07101718302D 43 49 0 0 1 0 0 0 0 0999 V2000 1.1400 -3.9948 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7481 -5.1332 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4787 -0.0553 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3623 -3.3239 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1714 -0.7449 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0697 -2.0959 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2104 -3.6927 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7481 -3.1784 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7481 -2.2010 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3407 -1.5101 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7825 -3.1444 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0552 -3.1784 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1154 -1.3326 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6433 -1.4448 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5673 -1.6153 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5100 -2.2754 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1960 -1.7806 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0898 -2.4548 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9017 -3.6671 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0759 -1.4786 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.0552 -2.2010 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9017 -1.7123 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2843 -1.2551 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7261 -2.8894 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2616 -1.2938 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8465 -0.4887 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.9769 -1.9447 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1463 -2.7099 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4335 -2.5304 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1826 -1.5858 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.3288 -1.5469 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.7264 -0.6540 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6984 -0.7562 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.5248 -1.2111 0.0000 N 0 0 3 0 0 0 0 0 0 0 0 0 -1.8954 -3.6546 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.2592 -3.2200 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.9017 -4.6445 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.5351 -0.3104 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.4187 -3.5790 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.9205 -1.6896 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3771 -2.7855 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.4536 -2.0203 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 7 1 0 0 0 0 2 37 1 0 0 0 0 3 38 1 0 0 0 0 4 39 1 0 0 0 0 5 40 1 0 0 0 0 6 41 1 0 0 0 0 7 17 2 0 0 0 0 8 9 2 0 0 0 0 8 19 1 0 0 0 0 9 22 1 0 0 0 0 10 18 2 0 0 0 0 10 23 1 0 0 0 0 11 18 1 0 0 0 0 11 24 2 0 0 0 0 12 19 2 0 0 0 0 12 21 1 0 0 0 0 13 20 1 0 0 0 0 13 25 1 0 0 0 0 14 26 1 0 0 0 0 14 31 1 0 0 0 0 15 17 1 0 0 0 0 15 34 1 0 0 0 0 16 30 1 0 0 0 0 16 42 1 0 0 0 0 17 20 1 0 0 0 0 18 28 1 0 0 0 0 19 37 1 0 0 0 0 20 30 1 6 0 0 0 21 22 2 0 0 0 0 21 31 1 0 0 0 0 22 33 1 0 0 0 0 23 27 2 0 0 0 0 23 38 1 0 0 0 0 24 27 1 0 0 0 0 24 39 1 0 0 0 0 25 32 1 6 0 0 0 25 34 1 0 0 0 0 26 34 1 1 0 0 0 26 43 1 0 0 0 0 27 40 1 0 0 0 0 28 35 2 0 0 0 0 28 42 1 0 0 0 0 29 30 1 0 0 0 0 29 36 2 0 0 0 0 29 41 1 0 0 0 0 30 31 1 1 0 0 0 31 32 1 1 0 0 0 32 33 1 1 0 0 0 32 43 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	592.24
Volume:	579.51
LogP:	3.679
LogD:	3.62
LogS:	-4.827
# Rotatable Bonds:	10
TPSA:	114.02
# H-Bond Aceptor:	11
# H-Bond Donor:	1
# Rings:	7
# Heavy Atoms:	11

MedChem Properties

QED Drug-Likeness Score:	0.359
Synthetic Accessibility Score:	6.34
Fsp3:	0.5
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:	-5.166
MDCK Permeability:	3.614325396483764e-05
Pgp-inhibitor:	0.854
Pgp-substrate:	0.011
Human Intestinal Absorption (HIA):	0.121
20% Bioavailability (F20%):	0.257
30% Bioavailability (F30%):	0.984

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.616
Plasma Protein Binding (PPB):	80.95541381835938%
Volume Distribution (VD):	1.181
Pgp-substrate:	14.917951583862305%

ADMET: Metabolism

CYP1A2-inhibitor:	0.078
CYP1A2-substrate:	0.912
CYP2C19-inhibitor:	0.616
CYP2C19-substrate:	0.884
CYP2C9-inhibitor:	0.545
CYP2C9-substrate:	0.529
CYP2D6-inhibitor:	0.281
CYP2D6-substrate:	0.864
CYP3A4-inhibitor:	0.951
CYP3A4-substrate:	0.922

ADMET: Excretion

Clearance (CL):	10.091
Half-life (T1/2):	0.276

ADMET: Toxicity

hERG Blockers:	0.072
Human Hepatotoxicity (H-HT):	0.917
Drug-inuced Liver Injury (DILI):	0.503
AMES Toxicity:	0.302
Rat Oral Acute Toxicity:	0.962
Maximum Recommended Daily Dose:	0.996
Skin Sensitization:	0.198
Carcinogencity:	0.96
Eye Corrosion:	0.003
Eye Irritation:	0.016
Respiratory Toxicity:	0.958

Download Data

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

Natural Product: NPC120239

Natural Product ID:	NPC120239
*Common Name:**	Alstiphyllanine F
IUPAC Name:	n.a.
Synonyms:	Alstiphyllanine F
Standard InCHIKey:	JIBNKPQBEIZZCU-DYWXBFQLSA-N
Standard InCHI:	InChI=1S/C32H36N2O9/c1-7-17-15-34-25-13-20(17)30(29(36)41-6,16-42-28(35)18-10-23(38-3)27(40-5)24(11-18)39-4)31-14-26(34)43-32(25,31)33-22-9-8-19(37-2)12-21(22)31/h7-12,20,25-26,33H,13-16H2,1-6H3/b17-7-/t20-,25-,26-,30-,31-,32-/m0/s1
SMILES:	C/C=C1/CN2[C@H]3C[C@@H]1[C@@](COC(=O)c1cc(c(c(c1)OC)OC)OC)(C(=O)OC)[C@]14C[C@@H]2O[C@@]34Nc2ccc(cc12)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL592521
PubChem CID:	46229072
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids and derivatives [CHEMONTID:0002750] Corynanthean-type alkaloids

*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
NPO19678	Alstonia macrophylla	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19191551]
NPO19678	Alstonia macrophylla	Species	Apocynaceae	Eukaryota	leaves	Purwodadi Botanical Garden, Indonesia	n.a.	PMID[20189404]
NPO19678	Alstonia macrophylla	Species	Apocynaceae	Eukaryota	n.a.	stem	n.a.	PMID[22148233]
NPO19678	Alstonia macrophylla	Species	Apocynaceae	Eukaryota	Barks	n.a.	n.a.	PMID[23806072]
NPO19678	Alstonia macrophylla	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO19678	Alstonia macrophylla	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19678	Alstonia macrophylla	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO19678	Alstonia macrophylla	Species	Apocynaceae	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	2
Others	2

Activity Type	# Activity
Individual Protein	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT640	Individual Protein	Sodium/glucose cotransporter 1	Homo sapiens	IC50	=	39000.0	nM	PMID[568394]
NPT641	Individual Protein	Sodium/glucose cotransporter 2	Homo sapiens	IC50	=	40000.0	nM	PMID[568394]
NPT640	Individual Protein	Sodium/glucose cotransporter 1	Homo sapiens	Inhibition	=	65.2	%	PMID[568394]
NPT641	Individual Protein	Sodium/glucose cotransporter 2	Homo sapiens	Inhibition	=	103.8	%	PMID[568394]

☑ 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 NPC120239 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	450
0.1-0.2	1980
0.2-0.3	5658
0.3-0.4	11598
0.4-0.5	8532
0.5-0.6	12787
0.6-0.7	1526
0.7-0.8	154
0.8-0.85	3
0.85-0.9	2
0.9-0.95	0
0.95-1	7

Similarity Score	Similarity Level	Natural Product ID
0.9861	High Similarity	NPC113455
0.9769	High Similarity	NPC304837
0.9769	High Similarity	NPC476258
0.963	High Similarity	NPC154922
0.9583	High Similarity	NPC476220
0.9583	High Similarity	NPC160113
0.8864	High Similarity	NPC231924
0.85	High Similarity	NPC234772
0.8304	Intermediate Similarity	NPC476429
0.8087	Intermediate Similarity	NPC476436
0.8008	Intermediate Similarity	NPC191489
0.7974	Intermediate Similarity	NPC195636
0.788	Intermediate Similarity	NPC100734
0.788	Intermediate Similarity	NPC315634
0.788	Intermediate Similarity	NPC88923
0.787	Intermediate Similarity	NPC476069
0.7857	Intermediate Similarity	NPC131977
0.7839	Intermediate Similarity	NPC139373
0.7821	Intermediate Similarity	NPC473458
0.7759	Intermediate Similarity	NPC128476
0.7754	Intermediate Similarity	NPC223242
0.775	Intermediate Similarity	NPC301501
0.7735	Intermediate Similarity	NPC19175
0.7727	Intermediate Similarity	NPC90967
0.7717	Intermediate Similarity	NPC34717
0.7685	Intermediate Similarity	NPC181928
0.768	Intermediate Similarity	NPC284685
0.7673	Intermediate Similarity	NPC477396
0.7669	Intermediate Similarity	NPC471513
0.7664	Intermediate Similarity	NPC329932
0.7664	Intermediate Similarity	NPC477393
0.7654	Intermediate Similarity	NPC469451
0.7654	Intermediate Similarity	NPC469452
0.7645	Intermediate Similarity	NPC469450
0.7593	Intermediate Similarity	NPC291173
0.7582	Intermediate Similarity	NPC477395
0.7566	Intermediate Similarity	NPC475147
0.7556	Intermediate Similarity	NPC2173
0.7556	Intermediate Similarity	NPC202771
0.7556	Intermediate Similarity	NPC119818
0.7556	Intermediate Similarity	NPC328700
0.7554	Intermediate Similarity	NPC87560
0.7554	Intermediate Similarity	NPC195120
0.7545	Intermediate Similarity	NPC226652
0.7545	Intermediate Similarity	NPC72788
0.7545	Intermediate Similarity	NPC120671
0.7545	Intermediate Similarity	NPC314100
0.7532	Intermediate Similarity	NPC268223
0.7523	Intermediate Similarity	NPC21425
0.7522	Intermediate Similarity	NPC207971
0.7521	Intermediate Similarity	NPC288110
0.7511	Intermediate Similarity	NPC475133
0.7489	Intermediate Similarity	NPC157983
0.7489	Intermediate Similarity	NPC118154
0.7489	Intermediate Similarity	NPC318525
0.7489	Intermediate Similarity	NPC10653
0.7479	Intermediate Similarity	NPC77777
0.7456	Intermediate Similarity	NPC246140
0.7456	Intermediate Similarity	NPC195787
0.7455	Intermediate Similarity	NPC215098
0.7455	Intermediate Similarity	NPC46744
0.7455	Intermediate Similarity	NPC473298
0.7455	Intermediate Similarity	NPC70290
0.7455	Intermediate Similarity	NPC124302
0.7455	Intermediate Similarity	NPC14622
0.7455	Intermediate Similarity	NPC73020
0.7439	Intermediate Similarity	NPC469722
0.7414	Intermediate Similarity	NPC159815
0.7412	Intermediate Similarity	NPC268077
0.7403	Intermediate Similarity	NPC269449
0.7388	Intermediate Similarity	NPC151171
0.7386	Intermediate Similarity	NPC477397
0.7359	Intermediate Similarity	NPC46990
0.7339	Intermediate Similarity	NPC10732
0.7339	Intermediate Similarity	NPC119722
0.7339	Intermediate Similarity	NPC127996
0.7311	Intermediate Similarity	NPC118189
0.7304	Intermediate Similarity	NPC476500
0.7301	Intermediate Similarity	NPC71124
0.7292	Intermediate Similarity	NPC115588
0.728	Intermediate Similarity	NPC251071
0.7273	Intermediate Similarity	NPC478075
0.7273	Intermediate Similarity	NPC222561
0.7269	Intermediate Similarity	NPC5374
0.7257	Intermediate Similarity	NPC182853
0.7249	Intermediate Similarity	NPC286135
0.7238	Intermediate Similarity	NPC76478
0.7227	Intermediate Similarity	NPC222046
0.7222	Intermediate Similarity	NPC295479
0.7222	Intermediate Similarity	NPC220241
0.7215	Intermediate Similarity	NPC126556
0.7203	Intermediate Similarity	NPC55470
0.7198	Intermediate Similarity	NPC308943
0.7186	Intermediate Similarity	NPC87714
0.7185	Intermediate Similarity	NPC134702
0.7162	Intermediate Similarity	NPC138830
0.716	Intermediate Similarity	NPC13249
0.7156	Intermediate Similarity	NPC329992
0.7155	Intermediate Similarity	NPC80472
0.7143	Intermediate Similarity	NPC141440
0.7131	Intermediate Similarity	NPC148391
0.7124	Intermediate Similarity	NPC254957
0.7119	Intermediate Similarity	NPC285254
0.7111	Intermediate Similarity	NPC25401
0.71	Intermediate Similarity	NPC1464
0.7095	Intermediate Similarity	NPC7560
0.7091	Intermediate Similarity	NPC35680
0.709	Intermediate Similarity	NPC248903
0.7078	Intermediate Similarity	NPC122886
0.7074	Intermediate Similarity	NPC83019
0.7074	Intermediate Similarity	NPC100863
0.7073	Intermediate Similarity	NPC473781
0.7073	Intermediate Similarity	NPC470631
0.7073	Intermediate Similarity	NPC35390
0.7066	Intermediate Similarity	NPC148124
0.7061	Intermediate Similarity	NPC125924
0.7061	Intermediate Similarity	NPC470646
0.7059	Intermediate Similarity	NPC298449
0.7059	Intermediate Similarity	NPC189661
0.7049	Intermediate Similarity	NPC26928
0.7048	Intermediate Similarity	NPC94499
0.7045	Intermediate Similarity	NPC473486
0.7045	Intermediate Similarity	NPC475316
0.7035	Intermediate Similarity	NPC22476
0.7031	Intermediate Similarity	NPC204580
0.7025	Intermediate Similarity	NPC99724
0.7018	Intermediate Similarity	NPC469815
0.7018	Intermediate Similarity	NPC469816
0.7017	Intermediate Similarity	NPC114468
0.7015	Intermediate Similarity	NPC195788
0.7015	Intermediate Similarity	NPC237901
0.7013	Intermediate Similarity	NPC474427
0.7012	Intermediate Similarity	NPC223590
0.7012	Intermediate Similarity	NPC256422
0.7008	Intermediate Similarity	NPC477394
0.7004	Intermediate Similarity	NPC471303
0.7004	Intermediate Similarity	NPC82541
0.7004	Intermediate Similarity	NPC63152
0.7004	Intermediate Similarity	NPC226708
0.7	Intermediate Similarity	NPC473837
0.6996	Remote Similarity	NPC473562
0.6991	Remote Similarity	NPC208890
0.6987	Remote Similarity	NPC2905
0.6979	Remote Similarity	NPC11708
0.6975	Remote Similarity	NPC116178
0.6966	Remote Similarity	NPC470484
0.6962	Remote Similarity	NPC474366
0.6962	Remote Similarity	NPC25961
0.6957	Remote Similarity	NPC475713
0.6957	Remote Similarity	NPC474432
0.6957	Remote Similarity	NPC66909
0.6949	Remote Similarity	NPC207873
0.6949	Remote Similarity	NPC100573
0.6946	Remote Similarity	NPC321166
0.6946	Remote Similarity	NPC217903
0.6946	Remote Similarity	NPC30749
0.694	Remote Similarity	NPC67904
0.6936	Remote Similarity	NPC261388
0.6929	Remote Similarity	NPC207620
0.6927	Remote Similarity	NPC474858
0.6926	Remote Similarity	NPC193906
0.6926	Remote Similarity	NPC23080
0.6923	Remote Similarity	NPC315914
0.692	Remote Similarity	NPC477160
0.6916	Remote Similarity	NPC5630
0.6916	Remote Similarity	NPC474059
0.6913	Remote Similarity	NPC33256
0.6912	Remote Similarity	NPC260909
0.6911	Remote Similarity	NPC329982
0.6907	Remote Similarity	NPC212123
0.6907	Remote Similarity	NPC198160
0.6906	Remote Similarity	NPC470042
0.6906	Remote Similarity	NPC329816
0.6904	Remote Similarity	NPC169716
0.6903	Remote Similarity	NPC14994
0.6901	Remote Similarity	NPC82056
0.69	Remote Similarity	NPC302001
0.6897	Remote Similarity	NPC241263
0.6888	Remote Similarity	NPC38964
0.6885	Remote Similarity	NPC46259
0.6883	Remote Similarity	NPC470480
0.688	Remote Similarity	NPC185031
0.6875	Remote Similarity	NPC159963
0.6875	Remote Similarity	NPC124658
0.6875	Remote Similarity	NPC227361
0.6872	Remote Similarity	NPC162694
0.687	Remote Similarity	NPC243626
0.6867	Remote Similarity	NPC211215
0.6867	Remote Similarity	NPC127178
0.6864	Remote Similarity	NPC477161
0.6858	Remote Similarity	NPC318068
0.6853	Remote Similarity	NPC234933
0.6853	Remote Similarity	NPC265642
0.6853	Remote Similarity	NPC218733
0.6853	Remote Similarity	NPC132874
0.6853	Remote Similarity	NPC138615
0.6846	Remote Similarity	NPC176113
0.6846	Remote Similarity	NPC290227
0.6844	Remote Similarity	NPC140311
0.6838	Remote Similarity	NPC64576

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 NPC120239 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	250
0.1-0.2	642
0.2-0.3	952
0.3-0.4	2211
0.4-0.5	2902
0.5-0.6	1809
0.6-0.7	364
0.7-0.8	20
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
0.8008	Intermediate Similarity	NPD7708	Approved
0.7957	Intermediate Similarity	NPD6625	Approved
0.788	Intermediate Similarity	NPD7803	Approved
0.768	Intermediate Similarity	NPD7956	Approved
0.768	Intermediate Similarity	NPD7955	Approved
0.7562	Intermediate Similarity	NPD4846	Phase 2
0.7556	Intermediate Similarity	NPD5005	Approved
0.7556	Intermediate Similarity	NPD5006	Approved
0.7455	Intermediate Similarity	NPD4420	Approved
0.7378	Intermediate Similarity	NPD5071	Phase 2
0.7366	Intermediate Similarity	NPD6723	Discontinued
0.7269	Intermediate Similarity	NPD7858	Clinical (unspecified phase)
0.7257	Intermediate Similarity	NPD6621	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD7278	Phase 2
0.725	Intermediate Similarity	NPD7279	Phase 2
0.7236	Intermediate Similarity	NPD7690	Clinical (unspecified phase)
0.7227	Intermediate Similarity	NPD2899	Discontinued
0.7208	Intermediate Similarity	NPD6997	Phase 2
0.7154	Intermediate Similarity	NPD7922	Phase 1
0.7137	Intermediate Similarity	NPD7048	Phase 3
0.7101	Intermediate Similarity	NPD8149	Discontinued
0.7095	Intermediate Similarity	NPD7907	Approved
0.7069	Intermediate Similarity	NPD7064	Clinical (unspecified phase)
0.7051	Intermediate Similarity	NPD5242	Approved
0.7046	Intermediate Similarity	NPD7827	Phase 1
0.7021	Intermediate Similarity	NPD4859	Phase 1
0.7015	Intermediate Similarity	NPD8465	Approved
0.7015	Intermediate Similarity	NPD8466	Approved
0.7015	Intermediate Similarity	NPD8467	Approved
0.6996	Remote Similarity	NPD7597	Clinical (unspecified phase)
0.6958	Remote Similarity	NPD7047	Phase 3
0.6957	Remote Similarity	NPD2973	Approved
0.6957	Remote Similarity	NPD2974	Approved
0.6957	Remote Similarity	NPD2975	Approved
0.694	Remote Similarity	NPD4107	Approved
0.694	Remote Similarity	NPD4580	Approved
0.6912	Remote Similarity	NPD8425	Approved
0.6912	Remote Similarity	NPD8459	Approved
0.6912	Remote Similarity	NPD8460	Approved
0.6912	Remote Similarity	NPD8426	Approved
0.6897	Remote Similarity	NPD6874	Approved
0.6889	Remote Similarity	NPD8427	Approved
0.6889	Remote Similarity	NPD8428	Approved
0.6889	Remote Similarity	NPD8429	Approved
0.6883	Remote Similarity	NPD7238	Clinical (unspecified phase)
0.6872	Remote Similarity	NPD4111	Phase 1
0.6872	Remote Similarity	NPD4665	Approved
0.6849	Remote Similarity	NPD5183	Approved
0.6849	Remote Similarity	NPD5186	Approved
0.6844	Remote Similarity	NPD5433	Clinical (unspecified phase)
0.6844	Remote Similarity	NPD3437	Discontinued
0.6842	Remote Similarity	NPD7223	Discontinued
0.6842	Remote Similarity	NPD7224	Discontinued
0.6842	Remote Similarity	NPD5896	Clinical (unspecified phase)
0.684	Remote Similarity	NPD5582	Discontinued
0.6838	Remote Similarity	NPD3452	Approved
0.6838	Remote Similarity	NPD6238	Discontinued
0.6838	Remote Similarity	NPD2493	Approved
0.6838	Remote Similarity	NPD3450	Approved
0.6838	Remote Similarity	NPD4482	Phase 3
0.6838	Remote Similarity	NPD2494	Approved
0.6832	Remote Similarity	NPD8461	Discontinued
0.6822	Remote Similarity	NPD4582	Approved
0.6822	Remote Similarity	NPD4583	Approved
0.6807	Remote Similarity	NPD4082	Approved
0.6795	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.6791	Remote Similarity	NPD8364	Approved
0.6791	Remote Similarity	NPD8363	Approved
0.679	Remote Similarity	NPD3940	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD6293	Clinical (unspecified phase)
0.678	Remote Similarity	NPD4004	Approved
0.678	Remote Similarity	NPD4002	Approved
0.677	Remote Similarity	NPD2971	Approved
0.677	Remote Similarity	NPD2968	Approved
0.6769	Remote Similarity	NPD7235	Clinical (unspecified phase)
0.6763	Remote Similarity	NPD4494	Approved
0.6763	Remote Similarity	NPD4492	Approved
0.6761	Remote Similarity	NPD3912	Discontinued
0.675	Remote Similarity	NPD5860	Discontinued
0.6748	Remote Similarity	NPD7805	Phase 3
0.6745	Remote Similarity	NPD7885	Phase 2
0.6745	Remote Similarity	NPD7886	Phase 2
0.6741	Remote Similarity	NPD8365	Clinical (unspecified phase)
0.674	Remote Similarity	NPD6851	Approved
0.674	Remote Similarity	NPD6853	Approved
0.674	Remote Similarity	NPD6021	Clinical (unspecified phase)
0.6737	Remote Similarity	NPD956	Clinical (unspecified phase)
0.6737	Remote Similarity	NPD7627	Approved
0.6737	Remote Similarity	NPD7626	Approved
0.6723	Remote Similarity	NPD7255	Clinical (unspecified phase)
0.6709	Remote Similarity	NPD7497	Discontinued
0.6707	Remote Similarity	NPD7186	Phase 3
0.6707	Remote Similarity	NPD3783	Clinical (unspecified phase)
0.6705	Remote Similarity	NPD6503	Clinical (unspecified phase)
0.6695	Remote Similarity	NPD6973	Clinical (unspecified phase)
0.6695	Remote Similarity	NPD7667	Clinical (unspecified phase)
0.6694	Remote Similarity	NPD5619	Clinical (unspecified phase)
0.6692	Remote Similarity	NPD8492	Approved
0.6681	Remote Similarity	NPD4040	Phase 1
0.6667	Remote Similarity	NPD6385	Approved
0.6667	Remote Similarity	NPD6386	Approved
0.6653	Remote Similarity	NPD5676	Approved
0.6653	Remote Similarity	NPD4493	Discontinued
0.6652	Remote Similarity	NPD2247	Approved
0.6652	Remote Similarity	NPD2681	Approved
0.6652	Remote Similarity	NPD2680	Approved
0.6652	Remote Similarity	NPD2249	Approved
0.6651	Remote Similarity	NPD5353	Approved
0.6643	Remote Similarity	NPD8489	Phase 1
0.6639	Remote Similarity	NPD7559	Phase 2
0.6629	Remote Similarity	NPD7862	Clinical (unspecified phase)
0.6627	Remote Similarity	NPD6199	Discontinued
0.6626	Remote Similarity	NPD7225	Discontinued
0.6624	Remote Similarity	NPD7880	Clinical (unspecified phase)
0.6624	Remote Similarity	NPD6321	Discontinued
0.6623	Remote Similarity	NPD5928	Phase 1
0.6612	Remote Similarity	NPD4997	Clinical (unspecified phase)
0.6611	Remote Similarity	NPD5102	Clinical (unspecified phase)
0.661	Remote Similarity	NPD7237	Clinical (unspecified phase)
0.6603	Remote Similarity	NPD8153	Approved
0.6603	Remote Similarity	NPD8152	Approved
0.6603	Remote Similarity	NPD8367	Approved
0.66	Remote Similarity	NPD7821	Clinical (unspecified phase)
0.6598	Remote Similarity	NPD4022	Approved
0.6598	Remote Similarity	NPD4455	Discontinued
0.6598	Remote Similarity	NPD3472	Approved
0.6597	Remote Similarity	NPD3057	Approved
0.6594	Remote Similarity	NPD6618	Phase 2
0.6594	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6591	Remote Similarity	NPD8463	Approved
0.6589	Remote Similarity	NPD7417	Discontinued
0.6584	Remote Similarity	NPD1945	Phase 1
0.658	Remote Similarity	NPD7906	Approved
0.6578	Remote Similarity	NPD5603	Clinical (unspecified phase)
0.6575	Remote Similarity	NPD4885	Approved
0.6564	Remote Similarity	NPD6297	Approved
0.6564	Remote Similarity	NPD6716	Phase 1
0.6562	Remote Similarity	NPD4481	Phase 3
0.656	Remote Similarity	NPD7820	Phase 3
0.6557	Remote Similarity	NPD3888	Discontinued
0.6556	Remote Similarity	NPD4596	Phase 1
0.6556	Remote Similarity	NPD7583	Approved
0.6555	Remote Similarity	NPD7566	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD5488	Discontinued
0.655	Remote Similarity	NPD7560	Approved
0.6549	Remote Similarity	NPD5600	Discontinued
0.6546	Remote Similarity	NPD8155	Clinical (unspecified phase)
0.6543	Remote Similarity	NPD3372	Discontinued
0.6542	Remote Similarity	NPD7891	Discontinued
0.6537	Remote Similarity	NPD4084	Clinical (unspecified phase)
0.6529	Remote Similarity	NPD2907	Approved
0.6529	Remote Similarity	NPD7585	Approved
0.6529	Remote Similarity	NPD2906	Approved
0.6529	Remote Similarity	NPD6593	Clinical (unspecified phase)
0.6528	Remote Similarity	NPD4926	Clinical (unspecified phase)
0.6527	Remote Similarity	NPD2972	Approved
0.6527	Remote Similarity	NPD3533	Approved
0.6527	Remote Similarity	NPD8358	Approved
0.6524	Remote Similarity	NPD2490	Approved
0.6524	Remote Similarity	NPD2488	Approved
0.6518	Remote Similarity	NPD5980	Discovery
0.6516	Remote Similarity	NPD683	Approved
0.6515	Remote Similarity	NPD7607	Clinical (unspecified phase)
0.6513	Remote Similarity	NPD5457	Discontinued
0.6513	Remote Similarity	NPD5483	Clinical (unspecified phase)
0.6509	Remote Similarity	NPD6608	Clinical (unspecified phase)
0.6507	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6502	Remote Similarity	NPD6107	Approved
0.6498	Remote Similarity	NPD4668	Phase 2
0.6498	Remote Similarity	NPD3006	Discontinued
0.6491	Remote Similarity	NPD6654	Clinical (unspecified phase)
0.6489	Remote Similarity	NPD6365	Clinical (unspecified phase)
0.6489	Remote Similarity	NPD2248	Approved
0.6489	Remote Similarity	NPD2246	Approved
0.6485	Remote Similarity	NPD7476	Discontinued
0.6483	Remote Similarity	NPD3964	Approved
0.6478	Remote Similarity	NPD7475	Clinical (unspecified phase)
0.6477	Remote Similarity	NPD6525	Clinical (unspecified phase)
0.6476	Remote Similarity	NPD5312	Approved
0.6476	Remote Similarity	NPD8156	Discontinued
0.6476	Remote Similarity	NPD5313	Approved
0.6475	Remote Similarity	NPD3893	Discontinued
0.6471	Remote Similarity	NPD8067	Phase 3
0.6468	Remote Similarity	NPD7262	Phase 1
0.6463	Remote Similarity	NPD7149	Clinical (unspecified phase)
0.6461	Remote Similarity	NPD7302	Phase 3
0.6461	Remote Similarity	NPD7300	Phase 3
0.6458	Remote Similarity	NPD2491	Approved
0.6458	Remote Similarity	NPD3448	Approved
0.6458	Remote Similarity	NPD6795	Clinical (unspecified phase)
0.6457	Remote Similarity	NPD5677	Discontinued
0.6454	Remote Similarity	NPD6160	Clinical (unspecified phase)
0.6437	Remote Similarity	NPD7930	Approved
0.6432	Remote Similarity	NPD8099	Discontinued
0.6432	Remote Similarity	NPD8252	Approved
0.6432	Remote Similarity	NPD8251	Approved
0.6431	Remote Similarity	NPD4981	Phase 2
0.6429	Remote Similarity	NPD5194	Approved
0.6429	Remote Similarity	NPD5197	Approved
0.6429	Remote Similarity	NPD6457	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