NPASS Compound

Structure

NPC476258 OpenBabel07101719252D 45 51 0 0 1 0 0 0 0 0999 V2000 1.1170 -3.9142 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3050 -0.0292 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1871 -2.1196 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6927 -5.0297 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3682 -0.0542 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.2340 -3.2568 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0469 -0.7299 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0280 -2.0536 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2062 -3.6183 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6927 -3.1143 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6927 -2.1566 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2733 -1.4797 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7062 -3.0810 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0339 -3.1143 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1131 -1.3057 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6303 -1.4156 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5559 -1.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4998 -2.2295 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1921 -1.7447 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0275 -2.4053 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8633 -3.5931 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0744 -1.4488 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.0339 -2.1566 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8633 -1.6777 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1979 -1.2298 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6307 -2.8311 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2563 -1.2677 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8294 -0.4789 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.8766 -1.9055 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1030 -2.6552 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4248 -2.4794 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1790 -1.5538 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.3222 -1.5157 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.7117 -0.6408 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6642 -0.7409 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.5143 -1.1867 0.0000 N 0 3 3 0 0 0 0 0 0 0 0 0 -1.8572 -3.5809 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.2539 -3.1551 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.8633 -4.5509 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.4437 -0.3041 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.3095 -3.5068 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.8011 -1.6555 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3493 -2.7293 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.4243 -1.9795 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 9 1 0 0 0 0 2 35 1 0 0 0 0 3 36 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 42 1 0 0 0 0 8 43 1 0 0 0 0 9 19 2 0 0 0 0 10 11 2 0 0 0 0 10 21 1 0 0 0 0 11 24 1 0 0 0 0 12 20 2 0 0 0 0 12 25 1 0 0 0 0 13 20 1 0 0 0 0 13 26 2 0 0 0 0 14 21 2 0 0 0 0 14 23 1 0 0 0 0 15 22 1 0 0 0 0 15 27 1 0 0 0 0 16 28 1 0 0 0 0 16 33 1 0 0 0 0 17 19 1 0 0 0 0 17 36 1 0 0 0 0 18 32 1 0 0 0 0 18 44 1 0 0 0 0 19 22 1 0 0 0 0 20 30 1 0 0 0 0 21 39 1 0 0 0 0 22 32 1 6 0 0 0 23 24 2 0 0 0 0 23 33 1 0 0 0 0 24 35 1 0 0 0 0 25 29 2 0 0 0 0 25 40 1 0 0 0 0 26 29 1 0 0 0 0 26 41 1 0 0 0 0 27 34 1 6 0 0 0 27 36 1 0 0 0 0 28 36 1 1 0 0 0 28 45 1 0 0 0 0 29 42 1 0 0 0 0 30 37 2 0 0 0 0 30 44 1 0 0 0 0 31 32 1 0 0 0 0 31 38 2 0 0 0 0 31 43 1 0 0 0 0 32 33 1 1 0 0 0 33 34 1 1 0 0 0 34 35 1 0 0 0 0 34 45 1 6 0 0 0 M CHG 1 36 1 M END $$$$

Physi-Chem Properties

Molecular Weight:	621.28
Volume:	615.42
LogP:	2.908
LogD:	3.444
LogS:	-3.222
# Rotatable Bonds:	10
TPSA:	101.99
# H-Bond Aceptor:	11
# H-Bond Donor:	0
# Rings:	7
# Heavy Atoms:	11

MedChem Properties

QED Drug-Likeness Score:	0.247
Synthetic Accessibility Score:	6.66
Fsp3:	0.529
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.515
MDCK Permeability:	3.0400289688259363e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.994
Human Intestinal Absorption (HIA):	0.998
20% Bioavailability (F20%):	1.0
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.308
Plasma Protein Binding (PPB):	68.95481872558594%
Volume Distribution (VD):	1.61
Pgp-substrate:	31.321197509765625%

ADMET: Metabolism

CYP1A2-inhibitor:	0.024
CYP1A2-substrate:	0.646
CYP2C19-inhibitor:	0.19
CYP2C19-substrate:	0.893
CYP2C9-inhibitor:	0.063
CYP2C9-substrate:	0.433
CYP2D6-inhibitor:	0.017
CYP2D6-substrate:	0.838
CYP3A4-inhibitor:	0.815
CYP3A4-substrate:	0.941

ADMET: Excretion

Clearance (CL):	10.08
Half-life (T1/2):	0.8

ADMET: Toxicity

hERG Blockers:	0.002
Human Hepatotoxicity (H-HT):	0.128
Drug-inuced Liver Injury (DILI):	0.276
AMES Toxicity:	0.368
Rat Oral Acute Toxicity:	0.993
Maximum Recommended Daily Dose:	0.999
Skin Sensitization:	0.179
Carcinogencity:	0.977
Eye Corrosion:	0.003
Eye Irritation:	0.022
Respiratory Toxicity:	0.966

Download Data

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

Natural Product: NPC476258

Natural Product ID:	NPC476258
*Common Name:**	Alstiphyllanine C
IUPAC Name:	n.a.
Synonyms:	Alstiphyllanine C
Standard InCHIKey:	WHACFBRHAHLZJN-AXWMRBGZSA-N
Standard InCHI:	InChI=1S/C34H41N2O9/c1-9-19-17-36(3)27-15-22(19)32(31(38)43-8,18-44-30(37)20-12-25(40-5)29(42-7)26(13-20)41-6)33-16-28(36)45-34(27,33)35(2)24-11-10-21(39-4)14-23(24)33/h9-14,22,27-28H,15-18H2,1-8H3/q+1/b19-9-/t22-,27-,28-,32-,33-,34-,36?/m0/s1
SMILES:	CC=C1C[N+]2(C3CC1C(C45C3(N(C6=C4C=C(C=C6)OC)C)OC2C5)(COC(=O)C7=CC(=C(C(=C7)OC)OC)OC)C(=O)OC)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL558934
PubChem CID:	45270515
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	3

Activity Type	# Activity
Cell Line	1
Individual Protein	2
Organism	1
Tissue	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT165	Cell Line	HeLa	Homo sapiens	IC50	>	25.0	ug.mL-1	PMID[544664]
NPT640	Individual Protein	Sodium/glucose cotransporter 1	Homo sapiens	Inhibition	=	-8.2	%	PMID[544665]
NPT641	Individual Protein	Sodium/glucose cotransporter 2	Homo sapiens	Inhibition	=	-6.1	%	PMID[544665]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	6.2	ug.mL-1	PMID[544664]
NPT177	Tissue	Aorta	Rattus norvegicus	Activity	=	40.0	%	PMID[544664]

☑ 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 NPC476258 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	454
0.1-0.2	1911
0.2-0.3	5185
0.3-0.4	11547
0.4-0.5	8196
0.5-0.6	13323
0.6-0.7	1879
0.7-0.8	189
0.8-0.85	4
0.85-0.9	2
0.9-0.95	1
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC304837
0.981	High Similarity	NPC160113
0.981	High Similarity	NPC476220
0.9769	High Similarity	NPC120239
0.963	High Similarity	NPC113455
0.9398	High Similarity	NPC154922
0.8698	High Similarity	NPC234772
0.8636	High Similarity	NPC231924
0.8489	Intermediate Similarity	NPC476429
0.8267	Intermediate Similarity	NPC476436
0.7991	Intermediate Similarity	NPC473458
0.7878	Intermediate Similarity	NPC191489
0.7835	Intermediate Similarity	NPC471513
0.7833	Intermediate Similarity	NPC477396
0.7832	Intermediate Similarity	NPC195636
0.7824	Intermediate Similarity	NPC477393
0.7751	Intermediate Similarity	NPC88923
0.7751	Intermediate Similarity	NPC315634
0.7751	Intermediate Similarity	NPC100734
0.7741	Intermediate Similarity	NPC477395
0.7729	Intermediate Similarity	NPC476069
0.7727	Intermediate Similarity	NPC202771
0.7727	Intermediate Similarity	NPC2173
0.7727	Intermediate Similarity	NPC119818
0.7727	Intermediate Similarity	NPC328700
0.7722	Intermediate Similarity	NPC131977
0.7719	Intermediate Similarity	NPC195120
0.7719	Intermediate Similarity	NPC87560
0.7717	Intermediate Similarity	NPC226652
0.7717	Intermediate Similarity	NPC120671
0.7717	Intermediate Similarity	NPC314100
0.7717	Intermediate Similarity	NPC72788
0.7702	Intermediate Similarity	NPC139373
0.77	Intermediate Similarity	NPC21425
0.7699	Intermediate Similarity	NPC268223
0.7692	Intermediate Similarity	NPC207971
0.7686	Intermediate Similarity	NPC288110
0.7652	Intermediate Similarity	NPC318525
0.7652	Intermediate Similarity	NPC118154
0.7652	Intermediate Similarity	NPC157983
0.7652	Intermediate Similarity	NPC10653
0.7626	Intermediate Similarity	NPC14622
0.7626	Intermediate Similarity	NPC46744
0.7626	Intermediate Similarity	NPC124302
0.7626	Intermediate Similarity	NPC215098
0.7626	Intermediate Similarity	NPC73020
0.7626	Intermediate Similarity	NPC70290
0.7619	Intermediate Similarity	NPC128476
0.7617	Intermediate Similarity	NPC223242
0.7615	Intermediate Similarity	NPC301501
0.7597	Intermediate Similarity	NPC19175
0.7578	Intermediate Similarity	NPC268077
0.7577	Intermediate Similarity	NPC159815
0.755	Intermediate Similarity	NPC284685
0.7542	Intermediate Similarity	NPC477397
0.7531	Intermediate Similarity	NPC329932
0.7521	Intermediate Similarity	NPC469452
0.7521	Intermediate Similarity	NPC469451
0.751	Intermediate Similarity	NPC469450
0.75	Intermediate Similarity	NPC90967
0.75	Intermediate Similarity	NPC127996
0.75	Intermediate Similarity	NPC10732
0.7489	Intermediate Similarity	NPC34717
0.7468	Intermediate Similarity	NPC118189
0.7467	Intermediate Similarity	NPC476500
0.7466	Intermediate Similarity	NPC71124
0.7458	Intermediate Similarity	NPC291173
0.7454	Intermediate Similarity	NPC181928
0.7432	Intermediate Similarity	NPC5374
0.7422	Intermediate Similarity	NPC475147
0.7414	Intermediate Similarity	NPC182853
0.7411	Intermediate Similarity	NPC286135
0.7393	Intermediate Similarity	NPC76478
0.7389	Intermediate Similarity	NPC195787
0.7389	Intermediate Similarity	NPC246140
0.7382	Intermediate Similarity	NPC222046
0.738	Intermediate Similarity	NPC295479
0.738	Intermediate Similarity	NPC220241
0.7368	Intermediate Similarity	NPC475133
0.7359	Intermediate Similarity	NPC55470
0.7357	Intermediate Similarity	NPC308943
0.7339	Intermediate Similarity	NPC77777
0.7339	Intermediate Similarity	NPC134702
0.7324	Intermediate Similarity	NPC329992
0.7321	Intermediate Similarity	NPC138830
0.7313	Intermediate Similarity	NPC80472
0.7311	Intermediate Similarity	NPC13249
0.7306	Intermediate Similarity	NPC141440
0.7306	Intermediate Similarity	NPC469722
0.7285	Intermediate Similarity	NPC254957
0.7284	Intermediate Similarity	NPC148391
0.7269	Intermediate Similarity	NPC285254
0.7261	Intermediate Similarity	NPC269449
0.7256	Intermediate Similarity	NPC35680
0.7254	Intermediate Similarity	NPC151171
0.7246	Intermediate Similarity	NPC7560
0.7238	Intermediate Similarity	NPC248903
0.7232	Intermediate Similarity	NPC83019
0.7227	Intermediate Similarity	NPC473298
0.722	Intermediate Similarity	NPC470646
0.722	Intermediate Similarity	NPC473781
0.722	Intermediate Similarity	NPC35390
0.722	Intermediate Similarity	NPC470631
0.7217	Intermediate Similarity	NPC46990
0.7215	Intermediate Similarity	NPC148124
0.7215	Intermediate Similarity	NPC251071
0.7207	Intermediate Similarity	NPC94499
0.7198	Intermediate Similarity	NPC119722
0.7197	Intermediate Similarity	NPC26928
0.719	Intermediate Similarity	NPC473486
0.719	Intermediate Similarity	NPC475316
0.7188	Intermediate Similarity	NPC204580
0.7173	Intermediate Similarity	NPC99724
0.7168	Intermediate Similarity	NPC474427
0.7167	Intermediate Similarity	NPC114468
0.7162	Intermediate Similarity	NPC226708
0.7162	Intermediate Similarity	NPC63152
0.7161	Intermediate Similarity	NPC256422
0.7156	Intermediate Similarity	NPC473562
0.7155	Intermediate Similarity	NPC82541
0.7155	Intermediate Similarity	NPC115588
0.7155	Intermediate Similarity	NPC477394
0.7149	Intermediate Similarity	NPC208890
0.7137	Intermediate Similarity	NPC2905
0.713	Intermediate Similarity	NPC222561
0.713	Intermediate Similarity	NPC478075
0.7124	Intermediate Similarity	NPC116178
0.7118	Intermediate Similarity	NPC470484
0.7111	Intermediate Similarity	NPC474432
0.7111	Intermediate Similarity	NPC475713
0.7111	Intermediate Similarity	NPC66909
0.71	Intermediate Similarity	NPC100573
0.71	Intermediate Similarity	NPC207873
0.7094	Intermediate Similarity	NPC217903
0.7094	Intermediate Similarity	NPC30749
0.7094	Intermediate Similarity	NPC321166
0.7093	Intermediate Similarity	NPC67904
0.7089	Intermediate Similarity	NPC474858
0.708	Intermediate Similarity	NPC193906
0.708	Intermediate Similarity	NPC23080
0.7076	Intermediate Similarity	NPC126556
0.7067	Intermediate Similarity	NPC33256
0.7066	Intermediate Similarity	NPC315914
0.7064	Intermediate Similarity	NPC329816
0.7056	Intermediate Similarity	NPC212123
0.7056	Intermediate Similarity	NPC198160
0.7054	Intermediate Similarity	NPC302001
0.7046	Intermediate Similarity	NPC82056
0.7043	Intermediate Similarity	NPC87714
0.7038	Intermediate Similarity	NPC470042
0.7034	Intermediate Similarity	NPC38964
0.7031	Intermediate Similarity	NPC1464
0.7029	Intermediate Similarity	NPC46259
0.7027	Intermediate Similarity	NPC162694
0.7025	Intermediate Similarity	NPC470480
0.7021	Intermediate Similarity	NPC124658
0.7021	Intermediate Similarity	NPC227361
0.702	Intermediate Similarity	NPC185031
0.7018	Intermediate Similarity	NPC127178
0.7008	Intermediate Similarity	NPC211215
0.7004	Intermediate Similarity	NPC234933
0.6992	Remote Similarity	NPC290227
0.6992	Remote Similarity	NPC318068
0.6987	Remote Similarity	NPC254045
0.6987	Remote Similarity	NPC140311
0.6987	Remote Similarity	NPC151470
0.6987	Remote Similarity	NPC471489
0.6987	Remote Similarity	NPC311781
0.6987	Remote Similarity	NPC64576
0.6987	Remote Similarity	NPC471512
0.6987	Remote Similarity	NPC201055
0.6982	Remote Similarity	NPC214629
0.6979	Remote Similarity	NPC305542
0.6979	Remote Similarity	NPC470481
0.6979	Remote Similarity	NPC470482
0.6964	Remote Similarity	NPC25401
0.6964	Remote Similarity	NPC1820
0.6962	Remote Similarity	NPC240684
0.696	Remote Similarity	NPC272706
0.6955	Remote Similarity	NPC27887
0.6953	Remote Similarity	NPC90185
0.6946	Remote Similarity	NPC223590
0.6942	Remote Similarity	NPC122886
0.6938	Remote Similarity	NPC129897
0.6936	Remote Similarity	NPC61731
0.6936	Remote Similarity	NPC186569
0.6933	Remote Similarity	NPC473837
0.6933	Remote Similarity	NPC475180
0.693	Remote Similarity	NPC100863
0.6929	Remote Similarity	NPC106593
0.6923	Remote Similarity	NPC476496
0.6923	Remote Similarity	NPC115906
0.6923	Remote Similarity	NPC168250
0.692	Remote Similarity	NPC189661
0.692	Remote Similarity	NPC473746
0.692	Remote Similarity	NPC312531
0.692	Remote Similarity	NPC298449
0.6916	Remote Similarity	NPC125924
0.691	Remote Similarity	NPC326895
0.6909	Remote Similarity	NPC190461

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 NPC476258 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	262
0.1-0.2	659
0.2-0.3	976
0.3-0.4	2155
0.4-0.5	2955
0.5-0.6	1740
0.6-0.7	382
0.7-0.8	21
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
0.7974	Intermediate Similarity	NPD6625	Approved
0.7878	Intermediate Similarity	NPD7708	Approved
0.7751	Intermediate Similarity	NPD7803	Approved
0.7727	Intermediate Similarity	NPD5006	Approved
0.7727	Intermediate Similarity	NPD5005	Approved
0.7722	Intermediate Similarity	NPD4846	Phase 2
0.7626	Intermediate Similarity	NPD4420	Approved
0.755	Intermediate Similarity	NPD7956	Approved
0.755	Intermediate Similarity	NPD7955	Approved
0.7421	Intermediate Similarity	NPD6621	Clinical (unspecified phase)
0.7382	Intermediate Similarity	NPD2899	Discontinued
0.7362	Intermediate Similarity	NPD6997	Phase 2
0.7284	Intermediate Similarity	NPD7048	Phase 3
0.7257	Intermediate Similarity	NPD7278	Phase 2
0.7257	Intermediate Similarity	NPD7279	Phase 2
0.7246	Intermediate Similarity	NPD7907	Approved
0.7232	Intermediate Similarity	NPD5071	Phase 2
0.7231	Intermediate Similarity	NPD6723	Discontinued
0.7225	Intermediate Similarity	NPD7064	Clinical (unspecified phase)
0.7217	Intermediate Similarity	NPD5242	Approved
0.7131	Intermediate Similarity	NPD7858	Clinical (unspecified phase)
0.7117	Intermediate Similarity	NPD7690	Clinical (unspecified phase)
0.7111	Intermediate Similarity	NPD2974	Approved
0.7111	Intermediate Similarity	NPD2975	Approved
0.7111	Intermediate Similarity	NPD2973	Approved
0.7106	Intermediate Similarity	NPD7047	Phase 3
0.7093	Intermediate Similarity	NPD4580	Approved
0.7093	Intermediate Similarity	NPD4107	Approved
0.7048	Intermediate Similarity	NPD6874	Approved
0.7035	Intermediate Similarity	NPD7238	Clinical (unspecified phase)
0.702	Intermediate Similarity	NPD7922	Phase 1
0.7017	Intermediate Similarity	NPD4665	Approved
0.7017	Intermediate Similarity	NPD4111	Phase 1
0.6991	Remote Similarity	NPD5582	Discontinued
0.6987	Remote Similarity	NPD2494	Approved
0.6987	Remote Similarity	NPD3452	Approved
0.6987	Remote Similarity	NPD3450	Approved
0.6987	Remote Similarity	NPD2493	Approved
0.6987	Remote Similarity	NPD4482	Phase 3
0.6983	Remote Similarity	NPD7224	Discontinued
0.6983	Remote Similarity	NPD7223	Discontinued
0.697	Remote Similarity	NPD4583	Approved
0.697	Remote Similarity	NPD4582	Approved
0.6965	Remote Similarity	NPD8461	Discontinued
0.6962	Remote Similarity	NPD8149	Discontinued
0.6943	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.6941	Remote Similarity	NPD6293	Clinical (unspecified phase)
0.6926	Remote Similarity	NPD4002	Approved
0.6926	Remote Similarity	NPD4004	Approved
0.6923	Remote Similarity	NPD2971	Approved
0.6923	Remote Similarity	NPD2968	Approved
0.6907	Remote Similarity	NPD7827	Phase 1
0.6894	Remote Similarity	NPD5860	Discontinued
0.6891	Remote Similarity	NPD8466	Approved
0.6891	Remote Similarity	NPD8465	Approved
0.6891	Remote Similarity	NPD8467	Approved
0.6888	Remote Similarity	NPD7805	Phase 3
0.6883	Remote Similarity	NPD956	Clinical (unspecified phase)
0.688	Remote Similarity	NPD7886	Phase 2
0.688	Remote Similarity	NPD7885	Phase 2
0.688	Remote Similarity	NPD4859	Phase 1
0.687	Remote Similarity	NPD7255	Clinical (unspecified phase)
0.6853	Remote Similarity	NPD7497	Discontinued
0.6853	Remote Similarity	NPD7597	Clinical (unspecified phase)
0.6846	Remote Similarity	NPD3437	Discontinued
0.6844	Remote Similarity	NPD7186	Phase 3
0.6842	Remote Similarity	NPD7667	Clinical (unspecified phase)
0.6831	Remote Similarity	NPD5619	Clinical (unspecified phase)
0.6825	Remote Similarity	NPD6386	Approved
0.6825	Remote Similarity	NPD6385	Approved
0.6822	Remote Similarity	NPD8492	Approved
0.6808	Remote Similarity	NPD5353	Approved
0.6793	Remote Similarity	NPD5676	Approved
0.679	Remote Similarity	NPD8460	Approved
0.679	Remote Similarity	NPD8426	Approved
0.679	Remote Similarity	NPD8459	Approved
0.679	Remote Similarity	NPD8425	Approved
0.6778	Remote Similarity	NPD7559	Phase 2
0.6767	Remote Similarity	NPD6321	Discontinued
0.6766	Remote Similarity	NPD8428	Approved
0.6766	Remote Similarity	NPD8427	Approved
0.6766	Remote Similarity	NPD8429	Approved
0.6765	Remote Similarity	NPD7225	Discontinued
0.6762	Remote Similarity	NPD3912	Discontinued
0.6756	Remote Similarity	NPD7862	Clinical (unspecified phase)
0.6751	Remote Similarity	NPD4997	Clinical (unspecified phase)
0.6741	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6738	Remote Similarity	NPD3057	Approved
0.6737	Remote Similarity	NPD4082	Approved
0.6735	Remote Similarity	NPD7821	Clinical (unspecified phase)
0.6732	Remote Similarity	NPD8367	Approved
0.6727	Remote Similarity	NPD5603	Clinical (unspecified phase)
0.6726	Remote Similarity	NPD7906	Approved
0.6722	Remote Similarity	NPD3940	Clinical (unspecified phase)
0.6719	Remote Similarity	NPD7417	Discontinued
0.6718	Remote Similarity	NPD8463	Approved
0.6712	Remote Similarity	NPD4481	Phase 3
0.6708	Remote Similarity	NPD5433	Clinical (unspecified phase)
0.6697	Remote Similarity	NPD5186	Approved
0.6697	Remote Similarity	NPD5183	Approved
0.6697	Remote Similarity	NPD5600	Discontinued
0.6696	Remote Similarity	NPD5896	Clinical (unspecified phase)
0.6695	Remote Similarity	NPD7566	Clinical (unspecified phase)
0.6695	Remote Similarity	NPD6238	Discontinued
0.6694	Remote Similarity	NPD7820	Phase 3
0.6693	Remote Similarity	NPD6716	Phase 1
0.668	Remote Similarity	NPD7560	Approved
0.668	Remote Similarity	NPD5488	Discontinued
0.6667	Remote Similarity	NPD3533	Approved
0.6667	Remote Similarity	NPD2906	Approved
0.6667	Remote Similarity	NPD8364	Approved
0.6667	Remote Similarity	NPD7626	Approved
0.6667	Remote Similarity	NPD2907	Approved
0.6667	Remote Similarity	NPD6021	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD8363	Approved
0.6667	Remote Similarity	NPD7627	Approved
0.6667	Remote Similarity	NPD6593	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD2972	Approved
0.6667	Remote Similarity	NPD2490	Approved
0.6667	Remote Similarity	NPD2488	Approved
0.6653	Remote Similarity	NPD683	Approved
0.6653	Remote Similarity	NPD7607	Clinical (unspecified phase)
0.6653	Remote Similarity	NPD5980	Discovery
0.6652	Remote Similarity	NPD6608	Clinical (unspecified phase)
0.6652	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6639	Remote Similarity	NPD3783	Clinical (unspecified phase)
0.6637	Remote Similarity	NPD6654	Clinical (unspecified phase)
0.6636	Remote Similarity	NPD6365	Clinical (unspecified phase)
0.6625	Remote Similarity	NPD4492	Approved
0.6625	Remote Similarity	NPD4494	Approved
0.6623	Remote Similarity	NPD7235	Clinical (unspecified phase)
0.6622	Remote Similarity	NPD5312	Approved
0.6622	Remote Similarity	NPD8156	Discontinued
0.6622	Remote Similarity	NPD5313	Approved
0.6617	Remote Similarity	NPD8365	Clinical (unspecified phase)
0.661	Remote Similarity	NPD4040	Phase 1
0.6607	Remote Similarity	NPD7149	Clinical (unspecified phase)
0.6606	Remote Similarity	NPD5677	Discontinued
0.6602	Remote Similarity	NPD6525	Clinical (unspecified phase)
0.66	Remote Similarity	NPD8067	Phase 3
0.6596	Remote Similarity	NPD3448	Approved
0.6596	Remote Similarity	NPD2491	Approved
0.6593	Remote Similarity	NPD6851	Approved
0.6593	Remote Similarity	NPD6853	Approved
0.6583	Remote Similarity	NPD4493	Discontinued
0.6577	Remote Similarity	NPD8251	Approved
0.6577	Remote Similarity	NPD8252	Approved
0.6577	Remote Similarity	NPD6503	Clinical (unspecified phase)
0.6577	Remote Similarity	NPD8099	Discontinued
0.6575	Remote Similarity	NPD2681	Approved
0.6575	Remote Similarity	NPD2247	Approved
0.6575	Remote Similarity	NPD2680	Approved
0.6575	Remote Similarity	NPD2249	Approved
0.6575	Remote Similarity	NPD6457	Approved
0.6574	Remote Similarity	NPD5978	Approved
0.6574	Remote Similarity	NPD5977	Approved
0.656	Remote Similarity	NPD6199	Discontinued
0.6555	Remote Similarity	NPD6973	Clinical (unspecified phase)
0.6555	Remote Similarity	NPD7263	Phase 2
0.6549	Remote Similarity	NPD3534	Clinical (unspecified phase)
0.6549	Remote Similarity	NPD7280	Phase 3
0.6549	Remote Similarity	NPD7281	Phase 3
0.6548	Remote Similarity	NPD7942	Clinical (unspecified phase)
0.6547	Remote Similarity	NPD3050	Clinical (unspecified phase)
0.6544	Remote Similarity	NPD5019	Clinical (unspecified phase)
0.6543	Remote Similarity	NPD5025	Approved
0.6538	Remote Similarity	NPD7811	Phase 3
0.6538	Remote Similarity	NPD7810	Phase 3
0.6538	Remote Similarity	NPD7237	Clinical (unspecified phase)
0.6538	Remote Similarity	NPD8285	Discontinued
0.6531	Remote Similarity	NPD5496	Approved
0.6529	Remote Similarity	NPD4455	Discontinued
0.6525	Remote Similarity	NPD8489	Phase 1
0.6516	Remote Similarity	NPD8404	Phase 2
0.6515	Remote Similarity	NPD1945	Phase 1
0.6513	Remote Similarity	NPD7174	Clinical (unspecified phase)
0.6489	Remote Similarity	NPD6211	Clinical (unspecified phase)
0.6488	Remote Similarity	NPD3888	Discontinued
0.6485	Remote Similarity	NPD7583	Approved
0.6485	Remote Similarity	NPD4596	Phase 1
0.6482	Remote Similarity	NPD6741	Clinical (unspecified phase)
0.6481	Remote Similarity	NPD7880	Clinical (unspecified phase)
0.6478	Remote Similarity	NPD5928	Phase 1
0.6476	Remote Similarity	NPD4577	Approved
0.6476	Remote Similarity	NPD4578	Approved
0.6475	Remote Similarity	NPD8152	Approved
0.6475	Remote Similarity	NPD8153	Approved
0.6471	Remote Similarity	NPD5102	Clinical (unspecified phase)
0.6468	Remote Similarity	NPD6788	Approved
0.6468	Remote Similarity	NPD3297	Approved
0.6466	Remote Similarity	NPD7262	Phase 1
0.6463	Remote Similarity	NPD4663	Approved
0.646	Remote Similarity	NPD6104	Discontinued
0.6459	Remote Similarity	NPD7432	Phase 2
0.6458	Remote Similarity	NPD3472	Approved
0.6458	Remote Similarity	NPD7585	Approved
0.6458	Remote Similarity	NPD4022	Approved
0.6454	Remote Similarity	NPD7654	Discontinued
0.6447	Remote Similarity	NPD6618	Phase 2
0.6444	Remote Similarity	NPD7925	Phase 2

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