NPASS Compound

Structure

CID10732 OpenBabel06191715332D 31 36 0 0 1 0 0 0 0 0999 V2000 -1.3494 0.3892 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1861 -1.3606 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6143 1.3756 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8420 -2.0470 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5801 -0.7386 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0861 -0.3537 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2679 -1.7119 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0006 -2.9224 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5308 -1.4620 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5312 0.4865 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6872 0.0003 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3385 -1.0763 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3387 -1.8457 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8444 -2.4352 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6870 -0.9748 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6872 -0.0003 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3743 -0.9751 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3744 -0.0007 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6874 -0.9741 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8429 -2.4356 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8438 0.4871 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8442 -1.4613 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0002 -0.9745 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8431 -1.4616 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8438 -0.4871 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.6302 -2.8903 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8437 1.3964 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2176 -1.4622 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2180 0.4861 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.1906 -1.1754 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 25 1 0 0 0 0 2 29 1 0 0 0 0 3 30 1 0 0 0 0 4 7 1 0 0 0 0 4 13 2 0 0 0 0 5 6 1 0 0 0 0 5 24 1 0 0 0 0 6 25 1 0 0 0 0 7 31 1 0 0 0 0 8 20 1 0 0 0 0 9 15 2 0 0 0 0 9 17 1 0 0 0 0 10 16 2 0 0 0 0 10 18 1 0 0 0 0 11 21 1 0 0 0 0 12 13 1 0 0 0 0 12 25 1 0 0 0 0 13 14 1 0 0 0 0 14 8 1 1 0 0 0 14 22 1 0 0 0 0 15 16 1 0 0 0 0 15 24 1 0 0 0 0 16 26 1 0 0 0 0 17 18 2 0 0 0 0 17 29 1 0 0 0 0 18 30 1 0 0 0 0 19 11 1 1 0 0 0 19 22 1 0 0 0 0 19 31 1 0 0 0 0 20 24 1 0 0 0 0 20 27 2 0 0 0 0 21 26 1 0 0 0 0 21 28 2 0 0 0 0 22 23 1 0 0 0 0 23 24 1 0 0 0 0 23 26 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	534.21
Volume:	513.64
LogP:	1.369
LogD:	1.018
LogS:	-4.203
# Rotatable Bonds:	5
TPSA:	162.73
# H-Bond Aceptor:	11
# H-Bond Donor:	2
# Rings:	5
# Heavy Atoms:	11

MedChem Properties

QED Drug-Likeness Score:	0.224
Synthetic Accessibility Score:	6.799
Fsp3:	0.741
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:	-5.331
MDCK Permeability:	9.940416202880442e-05
Pgp-inhibitor:	0.999
Pgp-substrate:	0.01
Human Intestinal Absorption (HIA):	0.56
20% Bioavailability (F20%):	0.012
30% Bioavailability (F30%):	0.994

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.464
Plasma Protein Binding (PPB):	40.583885192871094%
Volume Distribution (VD):	0.736
Pgp-substrate:	37.28765106201172%

ADMET: Metabolism

CYP1A2-inhibitor:	0.019
CYP1A2-substrate:	0.804
CYP2C19-inhibitor:	0.02
CYP2C19-substrate:	0.488
CYP2C9-inhibitor:	0.013
CYP2C9-substrate:	0.017
CYP2D6-inhibitor:	0.008
CYP2D6-substrate:	0.078
CYP3A4-inhibitor:	0.586
CYP3A4-substrate:	0.256

ADMET: Excretion

Clearance (CL):	2.884
Half-life (T1/2):	0.33

ADMET: Toxicity

hERG Blockers:	0.019
Human Hepatotoxicity (H-HT):	0.471
Drug-inuced Liver Injury (DILI):	0.901
AMES Toxicity:	0.031
Rat Oral Acute Toxicity:	0.443
Maximum Recommended Daily Dose:	0.035
Skin Sensitization:	0.39
Carcinogencity:	0.073
Eye Corrosion:	0.004
Eye Irritation:	0.011
Respiratory Toxicity:	0.885

Download Data

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

Natural Product: NPC10732

Natural Product ID:	NPC10732
*Common Name:**	Novacine
IUPAC Name:	n.a.
Synonyms:	Novacine
Standard InCHIKey:	POLBLONFVZXVPI-SVFVWZOVSA-N
Standard InCHI:	InChI=1S/C24H28N2O5/c1-25-6-5-24-15-9-17(29-2)18(30-3)10-16(15)26-21(28)11-19-22(23(24)26)14(8-20(24)27)13(12-25)4-7-31-19/h4,9-10,14,19,22-23H,5-8,11-12H2,1-3H3/t14-,19-,22-,23-,24+/m0/s1
SMILES:	COc1cc2c(cc1OC)N1[C@@H]3[C@@]42CCN(C)CC2=CCO[C@H]([C@@H]3[C@H]2CC4=O)CC1=O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2164627
PubChem CID:	12314414
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000211] Indoles and derivatives [CHEMONTID:0000210] Carbazoles

*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
NPO4386	Strychnos icaja	Species	Loganiaceae	Eukaryota	n.a.	leaf	n.a.	DOI[10.1016/0040-4020(73)80248-0]
NPO28245	Strychnos nux-vomica	Species	Loganiaceae	Eukaryota	n.a.	seed	n.a.	DOI[10.1016/j.tet.2012.03.006]
NPO28245	Strychnos nux-vomica	Species	Loganiaceae	Eukaryota	n.a.	seed	n.a.	PMID[10.1016/j.tet.2012.03.006]
NPO4386	Strychnos icaja	Species	Loganiaceae	Eukaryota	n.a.	root	n.a.	PMID[11170658]
NPO4386	Strychnos icaja	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11170658]
NPO4386	Strychnos icaja	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12398531]
NPO4386	Strychnos icaja	Species	Loganiaceae	Eukaryota	n.a.	root	n.a.	PMID[12560037]
NPO28245	Strychnos nux-vomica	Species	Loganiaceae	Eukaryota	n.a.	seed	n.a.	PMID[16317898]
NPO28245	Strychnos nux-vomica	Species	Loganiaceae	Eukaryota	n.a.	seed	n.a.	PMID[17449162]
NPO28245	Strychnos nux-vomica	Species	Loganiaceae	Eukaryota	n.a.	seed	n.a.	PMID[19235686]
NPO4386	Strychnos icaja	Species	Loganiaceae	Eukaryota	Root bark	Central Africa	n.a.	PMID[19299148]
NPO28245	Strychnos nux-vomica	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19666019]
NPO28245	Strychnos nux-vomica	Species	Loganiaceae	Eukaryota	n.a.	seed	n.a.	PMID[22707864]
NPO28245	Strychnos nux-vomica	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23088673]
NPO28245	Strychnos nux-vomica	Species	Loganiaceae	Eukaryota	n.a.	seed	n.a.	PMID[2393954]
NPO4386	Strychnos icaja	Species	Loganiaceae	Eukaryota	Roots	n.a.	n.a.	PMID[24593048]
NPO4386	Strychnos icaja	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25594733]
NPO28245	Strychnos nux-vomica	Species	Loganiaceae	Eukaryota	n.a.	seed	n.a.	PMID[25594733]
NPO4386	Strychnos icaja	Species	Loganiaceae	Eukaryota	n.a.	leaf	n.a.	PMID[4954818]
NPO28245	Strychnos nux-vomica	Species	Loganiaceae	Eukaryota	n.a.	seed	n.a.	PMID[7912074]
NPO28245	Strychnos nux-vomica	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO4386	Strychnos icaja	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28245	Strychnos nux-vomica	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4386	Strychnos icaja	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28245	Strychnos nux-vomica	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO28245	Strychnos nux-vomica	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4386	Strychnos icaja	Species	Loganiaceae	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	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT660	Cell Line	SW480	Homo sapiens	IC50	>	40000.0	nM	PMID[482298]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	>	40000.0	nM	PMID[482298]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	40000.0	nM	PMID[482298]
NPT659	Cell Line	SMMC-7721	Homo sapiens	IC50	>	40000.0	nM	PMID[482298]
NPT116	Cell Line	HL-60	Homo sapiens	IC50	>	40000.0	nM	PMID[482298]

☑ 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 NPC10732 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	433
0.1-0.2	1859
0.2-0.3	6356
0.3-0.4	11645
0.4-0.5	12866
0.5-0.6	8163
0.6-0.7	1234
0.7-0.8	125
0.8-0.85	10
0.85-0.9	5
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9086	High Similarity	NPC159815
0.8775	High Similarity	NPC10653
0.8775	High Similarity	NPC318525
0.8524	High Similarity	NPC470480
0.8434	Intermediate Similarity	NPC67904
0.8434	Intermediate Similarity	NPC138830
0.8359	Intermediate Similarity	NPC473004
0.8341	Intermediate Similarity	NPC470481
0.8341	Intermediate Similarity	NPC470482
0.825	Intermediate Similarity	NPC127178
0.8148	Intermediate Similarity	NPC96901
0.8144	Intermediate Similarity	NPC473007
0.809	Intermediate Similarity	NPC230313
0.8071	Intermediate Similarity	NPC473008
0.806	Intermediate Similarity	NPC100863
0.8	Intermediate Similarity	NPC268077
0.7961	Intermediate Similarity	NPC477161
0.7951	Intermediate Similarity	NPC207971
0.7917	Intermediate Similarity	NPC231924
0.791	Intermediate Similarity	NPC243626
0.7882	Intermediate Similarity	NPC71124
0.7857	Intermediate Similarity	NPC82541
0.785	Intermediate Similarity	NPC288110
0.784	Intermediate Similarity	NPC195636
0.7789	Intermediate Similarity	NPC21425
0.7763	Intermediate Similarity	NPC473458
0.7758	Intermediate Similarity	NPC291173
0.774	Intermediate Similarity	NPC475147
0.7731	Intermediate Similarity	NPC476069
0.7729	Intermediate Similarity	NPC473005
0.7707	Intermediate Similarity	NPC193906
0.7707	Intermediate Similarity	NPC23080
0.77	Intermediate Similarity	NPC473006
0.7696	Intermediate Similarity	NPC128476
0.7685	Intermediate Similarity	NPC254957
0.7678	Intermediate Similarity	NPC477160
0.7678	Intermediate Similarity	NPC475133
0.767	Intermediate Similarity	NPC5374
0.7667	Intermediate Similarity	NPC308943
0.7656	Intermediate Similarity	NPC14339
0.7653	Intermediate Similarity	NPC127996
0.7642	Intermediate Similarity	NPC269449
0.7636	Intermediate Similarity	NPC476436
0.7634	Intermediate Similarity	NPC476220
0.7634	Intermediate Similarity	NPC160113
0.7615	Intermediate Similarity	NPC46259
0.7593	Intermediate Similarity	NPC313327
0.7593	Intermediate Similarity	NPC126556
0.7591	Intermediate Similarity	NPC19175
0.7588	Intermediate Similarity	NPC477395
0.7581	Intermediate Similarity	NPC55470
0.7558	Intermediate Similarity	NPC77777
0.7536	Intermediate Similarity	NPC17677
0.7524	Intermediate Similarity	NPC41216
0.7523	Intermediate Similarity	NPC471513
0.7522	Intermediate Similarity	NPC477393
0.7512	Intermediate Similarity	NPC471489
0.75	Intermediate Similarity	NPC476258
0.75	Intermediate Similarity	NPC304837
0.7488	Intermediate Similarity	NPC119722
0.7488	Intermediate Similarity	NPC477186
0.7467	Intermediate Similarity	NPC476429
0.7465	Intermediate Similarity	NPC234772
0.7457	Intermediate Similarity	NPC477396
0.7455	Intermediate Similarity	NPC477397
0.7451	Intermediate Similarity	NPC473569
0.7445	Intermediate Similarity	NPC154922
0.7443	Intermediate Similarity	NPC222046
0.7421	Intermediate Similarity	NPC148124
0.7404	Intermediate Similarity	NPC161804
0.7383	Intermediate Similarity	NPC207873
0.7383	Intermediate Similarity	NPC100573
0.7379	Intermediate Similarity	NPC204970
0.7376	Intermediate Similarity	NPC99724
0.7366	Intermediate Similarity	NPC22689
0.7366	Intermediate Similarity	NPC474059
0.7366	Intermediate Similarity	NPC105055
0.734	Intermediate Similarity	NPC102760
0.7339	Intermediate Similarity	NPC120239
0.7336	Intermediate Similarity	NPC222561
0.7323	Intermediate Similarity	NPC214626
0.7323	Intermediate Similarity	NPC139085
0.7323	Intermediate Similarity	NPC251212
0.7291	Intermediate Similarity	NPC115906
0.7289	Intermediate Similarity	NPC248903
0.7284	Intermediate Similarity	NPC113455
0.7282	Intermediate Similarity	NPC475780
0.7281	Intermediate Similarity	NPC295479
0.7281	Intermediate Similarity	NPC220241
0.7277	Intermediate Similarity	NPC122886
0.7257	Intermediate Similarity	NPC74216
0.7256	Intermediate Similarity	NPC478075
0.7244	Intermediate Similarity	NPC266994
0.7244	Intermediate Similarity	NPC26928
0.724	Intermediate Similarity	NPC87560
0.724	Intermediate Similarity	NPC195120
0.7228	Intermediate Similarity	NPC222524
0.7215	Intermediate Similarity	NPC268223
0.7188	Intermediate Similarity	NPC71539
0.7188	Intermediate Similarity	NPC250960
0.7184	Intermediate Similarity	NPC214629
0.7169	Intermediate Similarity	NPC116178
0.7163	Intermediate Similarity	NPC87714
0.7163	Intermediate Similarity	NPC22476
0.7157	Intermediate Similarity	NPC24954
0.7156	Intermediate Similarity	NPC272706
0.715	Intermediate Similarity	NPC477259
0.715	Intermediate Similarity	NPC169387
0.7143	Intermediate Similarity	NPC287588
0.7143	Intermediate Similarity	NPC35680
0.7143	Intermediate Similarity	NPC90185
0.7136	Intermediate Similarity	NPC474427
0.7136	Intermediate Similarity	NPC321166
0.7136	Intermediate Similarity	NPC217903
0.7129	Intermediate Similarity	NPC285941
0.7129	Intermediate Similarity	NPC63152
0.7122	Intermediate Similarity	NPC179704
0.7116	Intermediate Similarity	NPC473460
0.7113	Intermediate Similarity	NPC29285
0.7108	Intermediate Similarity	NPC190461
0.7104	Intermediate Similarity	NPC298449
0.7098	Intermediate Similarity	NPC157983
0.7098	Intermediate Similarity	NPC118154
0.7097	Intermediate Similarity	NPC198160
0.7085	Intermediate Similarity	NPC182853
0.7083	Intermediate Similarity	NPC470484
0.707	Intermediate Similarity	NPC475747
0.7059	Intermediate Similarity	NPC85613
0.7059	Intermediate Similarity	NPC5167
0.7053	Intermediate Similarity	NPC116007
0.7051	Intermediate Similarity	NPC475816
0.705	Intermediate Similarity	NPC469915
0.7048	Intermediate Similarity	NPC477394
0.7044	Intermediate Similarity	NPC260075
0.7033	Intermediate Similarity	NPC174629
0.7033	Intermediate Similarity	NPC312531
0.7031	Intermediate Similarity	NPC311906
0.703	Intermediate Similarity	NPC474708
0.7028	Intermediate Similarity	NPC477258
0.7027	Intermediate Similarity	NPC189661
0.7014	Intermediate Similarity	NPC302001
0.7005	Intermediate Similarity	NPC249405
0.7	Intermediate Similarity	NPC470821
0.6995	Remote Similarity	NPC474432
0.6995	Remote Similarity	NPC475713
0.6991	Remote Similarity	NPC118189
0.6991	Remote Similarity	NPC474077
0.699	Remote Similarity	NPC113946
0.699	Remote Similarity	NPC27887
0.6985	Remote Similarity	NPC299582
0.698	Remote Similarity	NPC475845
0.6976	Remote Similarity	NPC11149
0.6972	Remote Similarity	NPC195787
0.6972	Remote Similarity	NPC246140
0.6955	Remote Similarity	NPC168250
0.6955	Remote Similarity	NPC471561
0.6952	Remote Similarity	NPC208890
0.6952	Remote Similarity	NPC45389
0.695	Remote Similarity	NPC476569
0.6934	Remote Similarity	NPC470485
0.6934	Remote Similarity	NPC203972
0.6931	Remote Similarity	NPC474324
0.6931	Remote Similarity	NPC57812
0.6927	Remote Similarity	NPC163829
0.6923	Remote Similarity	NPC119669
0.6919	Remote Similarity	NPC1820
0.6916	Remote Similarity	NPC66909
0.6916	Remote Similarity	NPC329830
0.6916	Remote Similarity	NPC76478
0.6916	Remote Similarity	NPC24228
0.6912	Remote Similarity	NPC65403
0.6905	Remote Similarity	NPC320088
0.6905	Remote Similarity	NPC162694
0.6905	Remote Similarity	NPC230098
0.6903	Remote Similarity	NPC37957
0.6897	Remote Similarity	NPC241055
0.6897	Remote Similarity	NPC477185
0.689	Remote Similarity	NPC276674
0.689	Remote Similarity	NPC475981
0.689	Remote Similarity	NPC83511
0.689	Remote Similarity	NPC474746
0.689	Remote Similarity	NPC33902
0.6886	Remote Similarity	NPC251071
0.6884	Remote Similarity	NPC234933
0.6884	Remote Similarity	NPC176983
0.6875	Remote Similarity	NPC298339
0.687	Remote Similarity	NPC285254
0.6869	Remote Similarity	NPC174783
0.6867	Remote Similarity	NPC474192
0.6867	Remote Similarity	NPC475720
0.6866	Remote Similarity	NPC214960
0.6866	Remote Similarity	NPC279527
0.6858	Remote Similarity	NPC473041
0.6858	Remote Similarity	NPC96321
0.6858	Remote Similarity	NPC134702
0.685	Remote Similarity	NPC205167
0.6847	Remote Similarity	NPC471604
0.6847	Remote Similarity	NPC284842
0.684	Remote Similarity	NPC470483
0.6837	Remote Similarity	NPC162440

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 NPC10732 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	249
0.1-0.2	685
0.2-0.3	896
0.3-0.4	2063
0.4-0.5	3083
0.5-0.6	1792
0.6-0.7	367
0.7-0.8	15
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
0.7653	Intermediate Similarity	NPD5312	Approved
0.7653	Intermediate Similarity	NPD5313	Approved
0.7464	Intermediate Similarity	NPD7255	Clinical (unspecified phase)
0.7452	Intermediate Similarity	NPD5071	Phase 2
0.7419	Intermediate Similarity	NPD7559	Phase 2
0.7393	Intermediate Similarity	NPD956	Clinical (unspecified phase)
0.7291	Intermediate Similarity	NPD2968	Approved
0.7291	Intermediate Similarity	NPD2971	Approved
0.7282	Intermediate Similarity	NPD6533	Clinical (unspecified phase)
0.7173	Intermediate Similarity	NPD3639	Approved
0.7173	Intermediate Similarity	NPD3640	Phase 3
0.7173	Intermediate Similarity	NPD3641	Approved
0.7156	Intermediate Similarity	NPD7279	Phase 2
0.7156	Intermediate Similarity	NPD7278	Phase 2
0.715	Intermediate Similarity	NPD6608	Clinical (unspecified phase)
0.7136	Intermediate Similarity	NPD5183	Approved
0.7136	Intermediate Similarity	NPD5186	Approved
0.713	Intermediate Similarity	NPD6625	Approved
0.713	Intermediate Similarity	NPD7174	Clinical (unspecified phase)
0.7123	Intermediate Similarity	NPD683	Approved
0.7103	Intermediate Similarity	NPD6238	Discontinued
0.7087	Intermediate Similarity	NPD6021	Clinical (unspecified phase)
0.7085	Intermediate Similarity	NPD6457	Approved
0.7081	Intermediate Similarity	NPD2490	Approved
0.7081	Intermediate Similarity	NPD2488	Approved
0.7072	Intermediate Similarity	NPD5025	Approved
0.7064	Intermediate Similarity	NPD4859	Phase 1
0.705	Intermediate Similarity	NPD4166	Phase 2
0.7044	Intermediate Similarity	NPD5600	Discontinued
0.7032	Intermediate Similarity	NPD3591	Approved
0.7032	Intermediate Similarity	NPD3592	Approved
0.7028	Intermediate Similarity	NPD5582	Discontinued
0.7026	Intermediate Similarity	NPD7110	Phase 1
0.7026	Intermediate Similarity	NPD7109	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD4997	Clinical (unspecified phase)
0.6991	Remote Similarity	NPD7805	Phase 3
0.6986	Remote Similarity	NPD5620	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD4846	Phase 2
0.6957	Remote Similarity	NPD7281	Phase 3
0.6957	Remote Similarity	NPD7280	Phase 3
0.6947	Remote Similarity	NPD7858	Clinical (unspecified phase)
0.693	Remote Similarity	NPD7820	Phase 3
0.6927	Remote Similarity	NPD4040	Phase 1
0.6919	Remote Similarity	NPD5525	Clinical (unspecified phase)
0.6916	Remote Similarity	NPD2974	Approved
0.6916	Remote Similarity	NPD2975	Approved
0.6916	Remote Similarity	NPD2973	Approved
0.6903	Remote Similarity	NPD2899	Discontinued
0.69	Remote Similarity	NPD7821	Clinical (unspecified phase)
0.6898	Remote Similarity	NPD4580	Approved
0.6898	Remote Similarity	NPD4107	Approved
0.6897	Remote Similarity	NPD6365	Clinical (unspecified phase)
0.6895	Remote Similarity	NPD7607	Clinical (unspecified phase)
0.6888	Remote Similarity	NPD6875	Approved
0.6888	Remote Similarity	NPD6876	Approved
0.6875	Remote Similarity	NPD3534	Clinical (unspecified phase)
0.6872	Remote Similarity	NPD5896	Clinical (unspecified phase)
0.6872	Remote Similarity	NPD3437	Discontinued
0.6866	Remote Similarity	NPD6321	Discontinued
0.6861	Remote Similarity	NPD7225	Discontinued
0.6837	Remote Similarity	NPD5564	Approved
0.6832	Remote Similarity	NPD6107	Approved
0.6827	Remote Similarity	NPD7803	Approved
0.6825	Remote Similarity	NPD7291	Discontinued
0.6822	Remote Similarity	NPD7048	Phase 3
0.6821	Remote Similarity	NPD6662	Clinical (unspecified phase)
0.6814	Remote Similarity	NPD4481	Phase 3
0.6812	Remote Similarity	NPD6997	Phase 2
0.6804	Remote Similarity	NPD7064	Clinical (unspecified phase)
0.6803	Remote Similarity	NPD4926	Clinical (unspecified phase)
0.6797	Remote Similarity	NPD7186	Phase 3
0.6796	Remote Similarity	NPD5334	Clinical (unspecified phase)
0.6795	Remote Similarity	NPD4885	Approved
0.6794	Remote Similarity	NPD5917	Clinical (unspecified phase)
0.6791	Remote Similarity	NPD7667	Clinical (unspecified phase)
0.6789	Remote Similarity	NPD2494	Approved
0.6789	Remote Similarity	NPD3452	Approved
0.6789	Remote Similarity	NPD2493	Approved
0.6789	Remote Similarity	NPD4482	Phase 3
0.6789	Remote Similarity	NPD3450	Approved
0.6786	Remote Similarity	NPD814	Clinical (unspecified phase)
0.6783	Remote Similarity	NPD3912	Discontinued
0.6781	Remote Similarity	NPD4981	Phase 2
0.6777	Remote Similarity	NPD4084	Clinical (unspecified phase)
0.6773	Remote Similarity	NPD4583	Approved
0.6773	Remote Similarity	NPD4582	Approved
0.677	Remote Similarity	NPD5562	Approved
0.677	Remote Similarity	NPD5561	Approved
0.677	Remote Similarity	NPD8149	Discontinued
0.6765	Remote Similarity	NPD7025	Clinical (unspecified phase)
0.6763	Remote Similarity	NPD5900	Clinical (unspecified phase)
0.6763	Remote Similarity	NPD7479	Phase 2
0.6762	Remote Similarity	NPD6851	Approved
0.6762	Remote Similarity	NPD6853	Approved
0.6761	Remote Similarity	NPD7955	Approved
0.6761	Remote Similarity	NPD7956	Approved
0.6759	Remote Similarity	NPD7238	Clinical (unspecified phase)
0.6758	Remote Similarity	NPD7626	Approved
0.6758	Remote Similarity	NPD3106	Clinical (unspecified phase)
0.6758	Remote Similarity	NPD7627	Approved
0.6758	Remote Similarity	NPD3057	Approved
0.6757	Remote Similarity	NPD8027	Approved
0.6757	Remote Similarity	NPD5658	Approved
0.6754	Remote Similarity	NPD4664	Clinical (unspecified phase)
0.675	Remote Similarity	NPD5977	Approved
0.675	Remote Similarity	NPD5978	Approved
0.6748	Remote Similarity	NPD4498	Clinical (unspecified phase)
0.6748	Remote Similarity	NPD5603	Clinical (unspecified phase)
0.6736	Remote Similarity	NPD6790	Phase 1
0.6731	Remote Similarity	NPD6297	Approved
0.6728	Remote Similarity	NPD4420	Approved
0.6727	Remote Similarity	NPD4004	Approved
0.6727	Remote Similarity	NPD4002	Approved
0.6717	Remote Similarity	NPD1337	Clinical (unspecified phase)
0.6715	Remote Similarity	NPD5521	Clinical (unspecified phase)
0.6712	Remote Similarity	NPD3416	Discontinued
0.6699	Remote Similarity	NPD7149	Clinical (unspecified phase)
0.6698	Remote Similarity	NPD3631	Phase 3
0.6697	Remote Similarity	NPD5102	Clinical (unspecified phase)
0.6697	Remote Similarity	NPD3297	Approved
0.6682	Remote Similarity	NPD6656	Clinical (unspecified phase)
0.6682	Remote Similarity	NPD5005	Approved
0.6682	Remote Similarity	NPD3448	Approved
0.6682	Remote Similarity	NPD5515	Phase 2
0.6682	Remote Similarity	NPD2972	Approved
0.6682	Remote Similarity	NPD2491	Approved
0.6682	Remote Similarity	NPD3533	Approved
0.6682	Remote Similarity	NPD5006	Approved
0.6682	Remote Similarity	NPD6618	Phase 2
0.6681	Remote Similarity	NPD3442	Approved
0.6681	Remote Similarity	NPD3441	Approved
0.668	Remote Similarity	NPD8460	Approved
0.668	Remote Similarity	NPD8459	Approved
0.6667	Remote Similarity	NPD7708	Approved
0.6667	Remote Similarity	NPD3349	Phase 2
0.6651	Remote Similarity	NPD6293	Clinical (unspecified phase)
0.6638	Remote Similarity	NPD4952	Phase 3
0.6634	Remote Similarity	NPD3051	Approved
0.6633	Remote Similarity	NPD4584	Approved
0.6625	Remote Similarity	NPD8016	Phase 3
0.6625	Remote Similarity	NPD8017	Clinical (unspecified phase)
0.6624	Remote Similarity	NPD6723	Discontinued
0.6624	Remote Similarity	NPD7922	Phase 1
0.6622	Remote Similarity	NPD3298	Approved
0.6622	Remote Similarity	NPD6644	Discontinued
0.662	Remote Similarity	NPD6046	Clinical (unspecified phase)
0.6618	Remote Similarity	NPD5602	Clinical (unspecified phase)
0.6609	Remote Similarity	NPD5496	Approved
0.6607	Remote Similarity	NPD4154	Approved
0.6602	Remote Similarity	NPD2970	Approved
0.6602	Remote Similarity	NPD2969	Approved
0.66	Remote Similarity	NPD4773	Phase 2
0.66	Remote Similarity	NPD4772	Phase 2
0.6595	Remote Similarity	NPD6824	Clinical (unspecified phase)
0.6593	Remote Similarity	NPD5676	Approved
0.6593	Remote Similarity	NPD6567	Clinical (unspecified phase)
0.6589	Remote Similarity	NPD5188	Clinical (unspecified phase)
0.6589	Remote Similarity	NPD8466	Approved
0.6589	Remote Similarity	NPD8465	Approved
0.6589	Remote Similarity	NPD8467	Approved
0.6588	Remote Similarity	NPD7132	Clinical (unspecified phase)
0.6585	Remote Similarity	NPD3984	Clinical (unspecified phase)
0.6585	Remote Similarity	NPD3983	Phase 3
0.6583	Remote Similarity	NPD6357	Discontinued
0.6581	Remote Similarity	NPD7224	Discontinued
0.6581	Remote Similarity	NPD7223	Discontinued
0.6571	Remote Similarity	NPD6654	Clinical (unspecified phase)
0.657	Remote Similarity	NPD6517	Phase 3
0.657	Remote Similarity	NPD27	Approved
0.657	Remote Similarity	NPD2489	Approved
0.657	Remote Similarity	NPD6716	Phase 1
0.6566	Remote Similarity	NPD6030	Approved
0.6566	Remote Similarity	NPD6031	Approved
0.6564	Remote Similarity	NPD7301	Phase 3
0.6556	Remote Similarity	NPD7560	Approved
0.6555	Remote Similarity	NPD4373	Phase 2
0.6549	Remote Similarity	NPD5914	Approved
0.6545	Remote Similarity	NPD1880	Phase 3
0.6545	Remote Similarity	NPD6874	Approved
0.6544	Remote Similarity	NPD7262	Phase 1
0.6538	Remote Similarity	NPD5966	Clinical (unspecified phase)
0.6537	Remote Similarity	NPD5823	Approved
0.6537	Remote Similarity	NPD6037	Discontinued
0.6535	Remote Similarity	NPD5294	Clinical (unspecified phase)
0.6534	Remote Similarity	NPD6228	Discontinued
0.652	Remote Similarity	NPD8091	Phase 3
0.6502	Remote Similarity	NPD7597	Clinical (unspecified phase)
0.65	Remote Similarity	NPD6877	Discontinued
0.65	Remote Similarity	NPD4668	Phase 2
0.6488	Remote Similarity	NPD4796	Discontinued
0.6485	Remote Similarity	NPD7298	Approved
0.6481	Remote Similarity	NPD7907	Approved
0.6481	Remote Similarity	NPD2845	Phase 2
0.6481	Remote Similarity	NPD2843	Phase 2
0.6478	Remote Similarity	NPD7047	Phase 3
0.6476	Remote Similarity	NPD3793	Phase 3
0.6471	Remote Similarity	NPD19	Approved
0.6471	Remote Similarity	NPD1743	Approved
0.6471	Remote Similarity	NPD1742	Approved
0.6468	Remote Similarity	NPD5610	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