NPASS Compound

Structure

NPC329833 OpenBabel07101719132D 50 62 0 0 1 0 0 0 0 0999 V2000 0.1861 3.4640 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0028 2.9560 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0104 2.1879 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2016 2.8992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8107 2.8670 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3337 3.3335 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3490 1.7972 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2202 1.7374 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0505 -2.9155 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9907 0.8947 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6776 0.9631 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3325 0.0601 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2405 -3.4432 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5668 0.7051 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8444 -0.4158 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7566 -0.4572 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7358 2.9771 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6310 1.1238 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2291 2.7412 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1366 -1.5125 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1640 1.1302 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9985 -1.9502 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1067 1.3443 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8085 -1.4225 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.3926 2.2678 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6722 -1.1798 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.4260 0.2462 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7921 1.7051 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6723 2.9428 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6799 2.1746 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2234 1.1403 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5406 1.8261 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.0638 1.3737 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.8946 -0.0196 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.7931 2.7630 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.1658 1.3064 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3634 1.7284 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.1535 -0.1399 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.3000 2.1968 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.6620 0.4184 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6431 0.9139 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.0032 3.3203 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.0846 -0.5472 0.0000 N 0 0 3 0 0 0 0 0 0 0 0 0 -3.5072 1.8395 0.0000 N 0 0 3 0 0 0 0 0 0 0 0 0 -3.0185 1.7839 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 -1.2924 -4.4085 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4571 0.6489 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3330 2.3237 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.1543 0.9183 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 4 2 0 0 0 0 1 5 1 0 0 0 0 2 3 2 0 0 0 0 2 6 1 0 0 0 0 3 7 1 0 0 0 0 4 8 1 0 0 0 0 5 28 2 0 0 0 0 6 29 2 0 0 0 0 7 30 2 0 0 0 0 8 31 2 0 0 0 0 9 13 1 0 0 0 0 9 22 2 0 0 0 0 10 14 1 0 0 0 0 10 23 2 0 0 0 0 11 12 1 0 0 0 0 11 41 1 0 0 0 0 12 43 1 0 0 0 0 13 47 1 0 0 0 0 14 50 1 0 0 0 0 15 27 2 0 0 0 0 16 34 1 0 0 0 0 17 35 1 0 0 0 0 18 36 1 0 0 0 0 19 32 1 0 0 0 0 19 42 1 0 0 0 0 20 22 1 0 0 0 0 20 43 1 0 0 0 0 21 23 1 0 0 0 0 21 44 1 0 0 0 0 22 24 1 0 0 0 0 23 25 1 0 0 0 0 24 16 1 6 0 0 0 24 26 1 0 0 0 0 25 17 1 6 0 0 0 25 37 1 0 0 0 0 26 15 1 1 0 0 0 26 38 1 0 0 0 0 27 32 1 0 0 0 0 27 40 1 0 0 0 0 28 31 1 0 0 0 0 28 41 1 0 0 0 0 29 30 1 0 0 0 0 29 42 1 0 0 0 0 30 45 1 0 0 0 0 31 46 1 0 0 0 0 32 44 1 6 0 0 0 33 18 1 6 0 0 0 33 37 1 0 0 0 0 33 50 1 0 0 0 0 34 41 1 1 0 0 0 34 43 1 0 0 0 0 35 42 1 1 0 0 0 35 44 1 0 0 0 0 36 45 1 0 0 0 0 36 48 2 0 0 0 0 37 39 1 0 0 0 0 38 41 1 0 0 0 0 38 46 1 0 0 0 0 39 42 1 0 0 0 0 39 45 1 0 0 0 0 40 46 1 0 0 0 0 40 49 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	666.32
Volume:	673.901
LogP:	2.263
LogD:	2.638
LogS:	-3.557
# Rotatable Bonds:	2
TPSA:	76.56
# H-Bond Aceptor:	8
# H-Bond Donor:	1
# Rings:	13
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.493
Synthetic Accessibility Score:	7.707
Fsp3:	0.524
Lipinski Rule-of-5:	Accepted
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:	-4.942
MDCK Permeability:	4.128599539399147e-05
Pgp-inhibitor:	0.999
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.887
20% Bioavailability (F20%):	0.93
30% Bioavailability (F30%):	0.982

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.364
Plasma Protein Binding (PPB):	75.94658660888672%
Volume Distribution (VD):	2.463
Pgp-substrate:	25.132596969604492%

ADMET: Metabolism

CYP1A2-inhibitor:	0.008
CYP1A2-substrate:	0.131
CYP2C19-inhibitor:	0.065
CYP2C19-substrate:	0.857
CYP2C9-inhibitor:	0.279
CYP2C9-substrate:	0.126
CYP2D6-inhibitor:	0.092
CYP2D6-substrate:	0.287
CYP3A4-inhibitor:	0.821
CYP3A4-substrate:	0.944

ADMET: Excretion

Clearance (CL):	5.328
Half-life (T1/2):	0.082

ADMET: Toxicity

hERG Blockers:	0.477
Human Hepatotoxicity (H-HT):	0.786
Drug-inuced Liver Injury (DILI):	0.954
AMES Toxicity:	0.012
Rat Oral Acute Toxicity:	0.966
Maximum Recommended Daily Dose:	0.997
Skin Sensitization:	0.629
Carcinogencity:	0.925
Eye Corrosion:	0.003
Eye Irritation:	0.005
Respiratory Toxicity:	0.972

Download Data

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

Natural Product: NPC329833

Natural Product ID:	NPC329833
*Common Name:**	Strychnogucine B
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	MMKIAHOGFMPKCT-YDBFCOOGSA-N
Standard InCHI:	InChI=1S/C42H42N4O4/c47-13-9-22-20-43-12-11-41-28-5-1-4-8-31(28)46-38(41)26(24(22)16-34(41)43)15-27(40(46)49)32-19-42-29-6-2-3-7-30(29)45-36(48)18-33-37(39(42)45)25-17-35(42)44(32)21-23(25)10-14-50-33/h1-10,15,24-26,32-35,37-39,47H,11-14,16-21H2/b22-9-/t24-,25-,26-,32+,33-,34-,35-,37+,38-,39-,41+,42+/m0/s1
SMILES:	OC/C=C1/CN2CC[C@@]34[C@@H]2C[C@@H]1[C@@H]1C=C([C@H]2C[C@@]56[C@H]7N2CC2=CCO[C@@H]8[C@H]([C@@H]5N(c5c6cccc5)C(=O)C8)[C@H]2C7)C(=O)N([C@H]31)c1c4cccc1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL501860
PubChem CID:	44559871
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids and derivatives [CHEMONTID:0002749] Strychnos 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
NPO4386	Strychnos icaja	Species	Loganiaceae	Eukaryota	n.a.	leaf	n.a.	DOI[10.1016/0040-4020(73)80248-0]
NPO4386	Strychnos icaja	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11170658]
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[12398531]
NPO4386	Strychnos icaja	Species	Loganiaceae	Eukaryota	n.a.	root	n.a.	PMID[12560037]
NPO4386	Strychnos icaja	Species	Loganiaceae	Eukaryota	Root bark	Central Africa	n.a.	PMID[19299148]
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]
NPO4386	Strychnos icaja	Species	Loganiaceae	Eukaryota	n.a.	leaf	n.a.	PMID[4954818]
NPO4386	Strychnos icaja	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO4386	Strychnos icaja	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
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	11
Others	14

Activity Type	# Activity
Cell Line	2
Organism	15
Others	8

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	IC50	>	15000.0	nM	PMID[484523]
NPT393	Cell Line	HCT-116	Homo sapiens	IC50	=	15000.0	nM	PMID[484524]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	617.0	nM	PMID[484523]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC90	=	3785.0	nM	PMID[484523]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	85.0	nM	PMID[484523]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC90	=	358.0	nM	PMID[484523]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	510.0	nM	PMID[484523]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC90	=	3228.0	nM	PMID[484523]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	202.0	nM	PMID[484523]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC90	=	1150.0	nM	PMID[484523]
NPT27	Others	Unspecified		IC50	=	15500.0	nM	PMID[484523]
NPT2	Others	Unspecified		Ratio IC50	>	24.3	n.a.	PMID[484523]
NPT2	Others	Unspecified		Ratio IC50	>	176.0	n.a.	PMID[484523]
NPT2	Others	Unspecified		Ratio IC50	=	25.12	n.a.	PMID[484523]
NPT2	Others	Unspecified		Ratio IC50	=	182.4	n.a.	PMID[484523]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	529.0	nM	PMID[484524]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	85.0	nM	PMID[484524]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC90	=	358.0	nM	PMID[484524]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	617.0	nM	PMID[484524]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC90	=	2240.0	nM	PMID[484524]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC90	=	3790.0	nM	PMID[484524]
NPT2	Others	Unspecified		Ratio IC50	=	24.3	n.a.	PMID[484524]
NPT2	Others	Unspecified		Ratio IC50	=	28.3	n.a.	PMID[484524]
NPT2	Others	Unspecified		Ratio IC50	=	176.4	n.a.	PMID[484524]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	85.0	nM	PMID[484525]

☑ 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 NPC329833 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	345
0.1-0.2	1430
0.2-0.3	3804
0.3-0.4	19257
0.4-0.5	14060
0.5-0.6	3135
0.6-0.7	545
0.7-0.8	102
0.8-0.85	10
0.85-0.9	6
0.9-0.95	1
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9505	High Similarity	NPC162440
0.8564	High Similarity	NPC139085
0.8564	High Similarity	NPC214626
0.8564	High Similarity	NPC251212
0.8533	High Similarity	NPC286994
0.8261	Intermediate Similarity	NPC473743
0.8226	Intermediate Similarity	NPC260075
0.8177	Intermediate Similarity	NPC105055
0.8177	Intermediate Similarity	NPC22689
0.8098	Intermediate Similarity	NPC63047
0.8098	Intermediate Similarity	NPC475248
0.8075	Intermediate Similarity	NPC320147
0.8065	Intermediate Similarity	NPC473880
0.7892	Intermediate Similarity	NPC475420
0.7684	Intermediate Similarity	NPC96901
0.7644	Intermediate Similarity	NPC475097
0.7635	Intermediate Similarity	NPC67904
0.7635	Intermediate Similarity	NPC138830
0.7634	Intermediate Similarity	NPC225319
0.7606	Intermediate Similarity	NPC472106
0.7513	Intermediate Similarity	NPC52262
0.7513	Intermediate Similarity	NPC476095
0.75	Intermediate Similarity	NPC472117
0.7433	Intermediate Similarity	NPC113946
0.7407	Intermediate Similarity	NPC472101
0.7407	Intermediate Similarity	NPC469741
0.7407	Intermediate Similarity	NPC472120
0.735	Intermediate Similarity	NPC285841
0.7316	Intermediate Similarity	NPC282339
0.7316	Intermediate Similarity	NPC99632
0.7304	Intermediate Similarity	NPC221687
0.7299	Intermediate Similarity	NPC471950
0.7299	Intermediate Similarity	NPC471945
0.7286	Intermediate Similarity	NPC97584
0.7268	Intermediate Similarity	NPC97100
0.7268	Intermediate Similarity	NPC473375
0.7264	Intermediate Similarity	NPC471951
0.7264	Intermediate Similarity	NPC471946
0.7259	Intermediate Similarity	NPC99043
0.7259	Intermediate Similarity	NPC218594
0.7245	Intermediate Similarity	NPC203202
0.7245	Intermediate Similarity	NPC264482
0.7243	Intermediate Similarity	NPC159815
0.7238	Intermediate Similarity	NPC186284
0.7238	Intermediate Similarity	NPC22082
0.7225	Intermediate Similarity	NPC301501
0.722	Intermediate Similarity	NPC223242
0.7217	Intermediate Similarity	NPC475259
0.7208	Intermediate Similarity	NPC186669
0.7204	Intermediate Similarity	NPC477173
0.7202	Intermediate Similarity	NPC214960
0.7202	Intermediate Similarity	NPC279527
0.719	Intermediate Similarity	NPC477179
0.7173	Intermediate Similarity	NPC248117
0.717	Intermediate Similarity	NPC470488
0.7169	Intermediate Similarity	NPC10653
0.7169	Intermediate Similarity	NPC318525
0.7166	Intermediate Similarity	NPC243756
0.7156	Intermediate Similarity	NPC254850
0.7156	Intermediate Similarity	NPC477178
0.7156	Intermediate Similarity	NPC477180
0.7156	Intermediate Similarity	NPC139373
0.7156	Intermediate Similarity	NPC477181
0.715	Intermediate Similarity	NPC475359
0.715	Intermediate Similarity	NPC191817
0.7135	Intermediate Similarity	NPC293458
0.713	Intermediate Similarity	NPC469452
0.7129	Intermediate Similarity	NPC475489
0.7128	Intermediate Similarity	NPC469915
0.7123	Intermediate Similarity	NPC477174
0.7123	Intermediate Similarity	NPC470490
0.712	Intermediate Similarity	NPC193410
0.7118	Intermediate Similarity	NPC469450
0.7095	Intermediate Similarity	NPC471512
0.7085	Intermediate Similarity	NPC6974
0.7083	Intermediate Similarity	NPC472102
0.7083	Intermediate Similarity	NPC309531
0.7077	Intermediate Similarity	NPC223595
0.7077	Intermediate Similarity	NPC167724
0.7077	Intermediate Similarity	NPC224970
0.7074	Intermediate Similarity	NPC154602
0.7071	Intermediate Similarity	NPC476441
0.707	Intermediate Similarity	NPC126066
0.7069	Intermediate Similarity	NPC329932
0.7068	Intermediate Similarity	NPC123241
0.7068	Intermediate Similarity	NPC61013
0.7056	Intermediate Similarity	NPC476425
0.7056	Intermediate Similarity	NPC469451
0.7031	Intermediate Similarity	NPC36495
0.7031	Intermediate Similarity	NPC131977
0.7016	Intermediate Similarity	NPC29285
0.701	Intermediate Similarity	NPC14994
0.6991	Remote Similarity	NPC475422
0.6981	Remote Similarity	NPC473005
0.698	Remote Similarity	NPC159963
0.6977	Remote Similarity	NPC470491
0.6972	Remote Similarity	NPC473006
0.6947	Remote Similarity	NPC122106
0.6927	Remote Similarity	NPC229484
0.6927	Remote Similarity	NPC469536
0.6912	Remote Similarity	NPC322621
0.6911	Remote Similarity	NPC478076
0.6908	Remote Similarity	NPC25401
0.6908	Remote Similarity	NPC276430
0.6907	Remote Similarity	NPC474058
0.6901	Remote Similarity	NPC52801
0.6898	Remote Similarity	NPC87755
0.6893	Remote Similarity	NPC292675
0.6892	Remote Similarity	NPC288110
0.6884	Remote Similarity	NPC242269
0.6881	Remote Similarity	NPC11149
0.6878	Remote Similarity	NPC473615
0.6862	Remote Similarity	NPC264589
0.686	Remote Similarity	NPC128582
0.6859	Remote Similarity	NPC285381
0.685	Remote Similarity	NPC329338
0.685	Remote Similarity	NPC469726
0.6847	Remote Similarity	NPC476428
0.6838	Remote Similarity	NPC469722
0.6829	Remote Similarity	NPC259626
0.6802	Remote Similarity	NPC471124
0.6792	Remote Similarity	NPC100863
0.6786	Remote Similarity	NPC286871
0.6786	Remote Similarity	NPC176983
0.6784	Remote Similarity	NPC472118
0.6783	Remote Similarity	NPC473486
0.6783	Remote Similarity	NPC475316
0.6782	Remote Similarity	NPC476326
0.678	Remote Similarity	NPC2933
0.6768	Remote Similarity	NPC472115
0.6768	Remote Similarity	NPC472114
0.6766	Remote Similarity	NPC470548
0.6748	Remote Similarity	NPC307396
0.6746	Remote Similarity	NPC203628
0.6745	Remote Similarity	NPC90967
0.6741	Remote Similarity	NPC222046
0.6739	Remote Similarity	NPC35390
0.6739	Remote Similarity	NPC473781
0.6739	Remote Similarity	NPC470631
0.6732	Remote Similarity	NPC256288
0.6729	Remote Similarity	NPC127178
0.672	Remote Similarity	NPC130251
0.6718	Remote Similarity	NPC104345
0.6717	Remote Similarity	NPC470069
0.6717	Remote Similarity	NPC52059
0.6716	Remote Similarity	NPC307640
0.6699	Remote Similarity	NPC5630
0.6684	Remote Similarity	NPC471122
0.6684	Remote Similarity	NPC469735
0.6682	Remote Similarity	NPC470489
0.6682	Remote Similarity	NPC470485
0.6681	Remote Similarity	NPC473458
0.6667	Remote Similarity	NPC471199
0.6667	Remote Similarity	NPC321211
0.6667	Remote Similarity	NPC471436
0.6667	Remote Similarity	NPC1464
0.665	Remote Similarity	NPC315368
0.665	Remote Similarity	NPC477159
0.6649	Remote Similarity	NPC212799
0.6638	Remote Similarity	NPC151171
0.6635	Remote Similarity	NPC473004
0.6634	Remote Similarity	NPC181138
0.6634	Remote Similarity	NPC210415
0.6634	Remote Similarity	NPC298851
0.6634	Remote Similarity	NPC276993
0.6634	Remote Similarity	NPC293255
0.6634	Remote Similarity	NPC21752
0.6632	Remote Similarity	NPC66936
0.6632	Remote Similarity	NPC475763
0.6622	Remote Similarity	NPC10732
0.6622	Remote Similarity	NPC127996
0.662	Remote Similarity	NPC232600
0.662	Remote Similarity	NPC303214
0.6615	Remote Similarity	NPC473297
0.6606	Remote Similarity	NPC87714
0.6599	Remote Similarity	NPC276085
0.6599	Remote Similarity	NPC263709
0.6599	Remote Similarity	NPC97380
0.6599	Remote Similarity	NPC243673
0.6599	Remote Similarity	NPC310403
0.6599	Remote Similarity	NPC148468
0.6599	Remote Similarity	NPC63210
0.6594	Remote Similarity	NPC115588
0.6592	Remote Similarity	NPC475602
0.6589	Remote Similarity	NPC472541
0.6589	Remote Similarity	NPC472542
0.6588	Remote Similarity	NPC470483
0.6584	Remote Similarity	NPC355
0.6578	Remote Similarity	NPC15384
0.6578	Remote Similarity	NPC244425
0.6573	Remote Similarity	NPC34717
0.6558	Remote Similarity	NPC138615
0.6558	Remote Similarity	NPC265642
0.6558	Remote Similarity	NPC218733
0.6558	Remote Similarity	NPC132874
0.6549	Remote Similarity	NPC77777
0.6548	Remote Similarity	NPC211525
0.6548	Remote Similarity	NPC222029
0.6548	Remote Similarity	NPC153694
0.6542	Remote Similarity	NPC472539

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 NPC329833 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	205
0.1-0.2	601
0.2-0.3	727
0.3-0.4	2262
0.4-0.5	3816
0.5-0.6	1454
0.6-0.7	82
0.7-0.8	3
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
0.7405	Intermediate Similarity	NPD8400	Approved
0.7405	Intermediate Similarity	NPD8402	Approved
0.7405	Intermediate Similarity	NPD8401	Approved
0.6908	Remote Similarity	NPD8240	Discontinued
0.6825	Remote Similarity	NPD7794	Clinical (unspecified phase)
0.6808	Remote Similarity	NPD6805	Discontinued
0.68	Remote Similarity	NPD5997	Discontinued
0.6766	Remote Similarity	NPD3423	Phase 2
0.6766	Remote Similarity	NPD3422	Phase 3
0.6713	Remote Similarity	NPD7205	Discontinued
0.6603	Remote Similarity	NPD8103	Clinical (unspecified phase)
0.6548	Remote Similarity	NPD8630	Approved
0.6531	Remote Similarity	NPD5742	Approved
0.6531	Remote Similarity	NPD5743	Approved
0.6531	Remote Similarity	NPD5741	Approved
0.6497	Remote Similarity	NPD6395	Phase 2
0.6497	Remote Similarity	NPD6396	Clinical (unspecified phase)
0.6493	Remote Similarity	NPD6608	Clinical (unspecified phase)
0.648	Remote Similarity	NPD4121	Phase 3
0.648	Remote Similarity	NPD4120	Approved
0.6474	Remote Similarity	NPD6566	Discontinued
0.644	Remote Similarity	NPD4430	Phase 2
0.6435	Remote Similarity	NPD6995	Phase 1
0.6432	Remote Similarity	NPD7921	Approved
0.6432	Remote Similarity	NPD5504	Discontinued
0.6422	Remote Similarity	NPD7186	Phase 3
0.6415	Remote Similarity	NPD8025	Phase 2
0.6406	Remote Similarity	NPD7487	Discontinued
0.6396	Remote Similarity	NPD6518	Discontinued
0.6394	Remote Similarity	NPD6878	Phase 2
0.6394	Remote Similarity	NPD6879	Phase 2
0.639	Remote Similarity	NPD3377	Discontinued
0.6386	Remote Similarity	NPD7591	Clinical (unspecified phase)
0.6373	Remote Similarity	NPD3376	Clinical (unspecified phase)
0.6373	Remote Similarity	NPD7795	Phase 2
0.6368	Remote Similarity	NPD6891	Phase 2
0.6359	Remote Similarity	NPD3828	Approved
0.6356	Remote Similarity	NPD7595	Discontinued
0.6351	Remote Similarity	NPD6557	Phase 2
0.6338	Remote Similarity	NPD4334	Discontinued
0.6335	Remote Similarity	NPD7064	Clinical (unspecified phase)
0.6333	Remote Similarity	NPD8658	Clinical (unspecified phase)
0.6333	Remote Similarity	NPD8281	Discontinued
0.6329	Remote Similarity	NPD7950	Approved
0.6329	Remote Similarity	NPD7952	Approved
0.6329	Remote Similarity	NPD7951	Approved
0.6329	Remote Similarity	NPD7790	Approved
0.6329	Remote Similarity	NPD7953	Approved
0.6329	Remote Similarity	NPD7791	Approved
0.6329	Remote Similarity	NPD7789	Approved
0.6326	Remote Similarity	NPD8146	Phase 2
0.6316	Remote Similarity	NPD4330	Approved
0.6316	Remote Similarity	NPD4329	Approved
0.6301	Remote Similarity	NPD6661	Clinical (unspecified phase)
0.63	Remote Similarity	NPD5715	Clinical (unspecified phase)
0.6298	Remote Similarity	NPD3792	Approved
0.6291	Remote Similarity	NPD7683	Discontinued
0.629	Remote Similarity	NPD5721	Clinical (unspecified phase)
0.6289	Remote Similarity	NPD7295	Approved
0.6289	Remote Similarity	NPD6017	Discontinued
0.628	Remote Similarity	NPD5919	Clinical (unspecified phase)
0.6275	Remote Similarity	NPD8002	Clinical (unspecified phase)
0.6275	Remote Similarity	NPD8003	Clinical (unspecified phase)
0.6271	Remote Similarity	NPD7824	Approved
0.6269	Remote Similarity	NPD7599	Phase 2
0.6268	Remote Similarity	NPD2869	Clinical (unspecified phase)
0.6266	Remote Similarity	NPD8017	Clinical (unspecified phase)
0.6266	Remote Similarity	NPD8016	Phase 3
0.6262	Remote Similarity	NPD5727	Clinical (unspecified phase)
0.625	Remote Similarity	NPD7569	Approved
0.625	Remote Similarity	NPD7570	Approved
0.6245	Remote Similarity	NPD7688	Phase 1
0.6243	Remote Similarity	NPD2791	Discontinued
0.6238	Remote Similarity	NPD7600	Phase 2
0.6238	Remote Similarity	NPD2506	Approved
0.6237	Remote Similarity	NPD5918	Discontinued
0.6233	Remote Similarity	NPD8114	Approved
0.6233	Remote Similarity	NPD8115	Approved
0.6223	Remote Similarity	NPD6740	Clinical (unspecified phase)
0.622	Remote Similarity	NPD8006	Clinical (unspecified phase)
0.6217	Remote Similarity	NPD8000	Clinical (unspecified phase)
0.6215	Remote Similarity	NPD6484	Approved
0.6215	Remote Similarity	NPD6483	Approved
0.621	Remote Similarity	NPD7238	Clinical (unspecified phase)
0.6209	Remote Similarity	NPD4775	Clinical (unspecified phase)
0.6209	Remote Similarity	NPD3471	Approved
0.6209	Remote Similarity	NPD3470	Approved
0.6205	Remote Similarity	NPD4901	Clinical (unspecified phase)
0.6204	Remote Similarity	NPD6659	Phase 2
0.6202	Remote Similarity	NPD7449	Clinical (unspecified phase)
0.6199	Remote Similarity	NPD4600	Approved
0.6199	Remote Similarity	NPD4601	Approved
0.6198	Remote Similarity	NPD7560	Approved
0.6197	Remote Similarity	NPD6021	Clinical (unspecified phase)
0.619	Remote Similarity	NPD5900	Clinical (unspecified phase)
0.6186	Remote Similarity	NPD2820	Phase 3
0.6186	Remote Similarity	NPD7730	Approved
0.6186	Remote Similarity	NPD7731	Approved
0.6179	Remote Similarity	NPD7962	Phase 2
0.6175	Remote Similarity	NPD4315	Phase 2
0.6174	Remote Similarity	NPD8149	Discontinued
0.6174	Remote Similarity	NPD7218	Clinical (unspecified phase)
0.6169	Remote Similarity	NPD6855	Clinical (unspecified phase)
0.616	Remote Similarity	NPD8459	Approved
0.616	Remote Similarity	NPD8460	Approved
0.615	Remote Similarity	NPD7665	Phase 2
0.615	Remote Similarity	NPD2790	Discontinued
0.615	Remote Similarity	NPD7666	Phase 3
0.6146	Remote Similarity	NPD5430	Discontinued
0.6143	Remote Similarity	NPD5521	Clinical (unspecified phase)
0.6139	Remote Similarity	NPD7735	Clinical (unspecified phase)
0.6136	Remote Similarity	NPD7572	Phase 2
0.6134	Remote Similarity	NPD6768	Approved
0.6134	Remote Similarity	NPD2365	Approved
0.6133	Remote Similarity	NPD6732	Clinical (unspecified phase)
0.6131	Remote Similarity	NPD7606	Phase 3
0.6124	Remote Similarity	NPD7940	Phase 3
0.6122	Remote Similarity	NPD5933	Phase 3
0.6122	Remote Similarity	NPD5932	Phase 3
0.6122	Remote Similarity	NPD5931	Phase 3
0.6117	Remote Similarity	NPD5823	Approved
0.6114	Remote Similarity	NPD7881	Approved
0.6114	Remote Similarity	NPD3782	Discontinued
0.6113	Remote Similarity	NPD8358	Approved
0.6108	Remote Similarity	NPD2427	Approved
0.6106	Remote Similarity	NPD2431	Approved
0.6106	Remote Similarity	NPD2432	Approved
0.6103	Remote Similarity	NPD7082	Approved
0.6102	Remote Similarity	NPD7271	Approved
0.6092	Remote Similarity	NPD7780	Approved
0.6092	Remote Similarity	NPD7781	Approved
0.6091	Remote Similarity	NPD5411	Discontinued
0.6087	Remote Similarity	NPD2037	Approved
0.6085	Remote Similarity	NPD6654	Clinical (unspecified phase)
0.6085	Remote Similarity	NPD8311	Discontinued
0.6083	Remote Similarity	NPD7797	Approved
0.6083	Remote Similarity	NPD7796	Approved
0.6083	Remote Similarity	NPD5928	Phase 1
0.6077	Remote Similarity	NPD7854	Phase 2
0.6075	Remote Similarity	NPD5923	Phase 1
0.6075	Remote Similarity	NPD8241	Phase 2
0.6071	Remote Similarity	NPD7259	Approved
0.607	Remote Similarity	NPD5086	Approved
0.6069	Remote Similarity	NPD8466	Approved
0.6069	Remote Similarity	NPD8465	Approved
0.6069	Remote Similarity	NPD8467	Approved
0.6068	Remote Similarity	NPD7858	Clinical (unspecified phase)
0.6068	Remote Similarity	NPD7793	Clinical (unspecified phase)
0.6062	Remote Similarity	NPD6655	Clinical (unspecified phase)
0.6062	Remote Similarity	NPD7001	Phase 3
0.6061	Remote Similarity	NPD7441	Clinical (unspecified phase)
0.6061	Remote Similarity	NPD8165	Discontinued
0.6061	Remote Similarity	NPD7478	Approved
0.6055	Remote Similarity	NPD3785	Clinical (unspecified phase)
0.6054	Remote Similarity	NPD4501	Approved
0.6054	Remote Similarity	NPD4500	Approved
0.6053	Remote Similarity	NPD5834	Phase 3
0.6053	Remote Similarity	NPD5835	Phase 3
0.6048	Remote Similarity	NPD5466	Approved
0.6041	Remote Similarity	NPD6622	Phase 1
0.603	Remote Similarity	NPD4682	Phase 2
0.603	Remote Similarity	NPD5942	Approved
0.603	Remote Similarity	NPD5941	Approved
0.6027	Remote Similarity	NPD6238	Discontinued
0.6027	Remote Similarity	NPD6321	Discontinued
0.6026	Remote Similarity	NPD5860	Discontinued
0.6025	Remote Similarity	NPD7710	Clinical (unspecified phase)
0.6023	Remote Similarity	NPD8364	Approved
0.6023	Remote Similarity	NPD8363	Approved
0.602	Remote Similarity	NPD4464	Clinical (unspecified phase)
0.6019	Remote Similarity	NPD3978	Clinical (unspecified phase)
0.6019	Remote Similarity	NPD2083	Clinical (unspecified phase)
0.6011	Remote Similarity	NPD4549	Discontinued
0.601	Remote Similarity	NPD2455	Approved
0.601	Remote Similarity	NPD2404	Discontinued
0.601	Remote Similarity	NPD2454	Approved
0.6009	Remote Similarity	NPD2916	Discontinued
0.6009	Remote Similarity	NPD6874	Approved
0.6009	Remote Similarity	NPD6999	Discontinued
0.6009	Remote Similarity	NPD2907	Approved
0.6009	Remote Similarity	NPD7000	Clinical (unspecified phase)
0.6009	Remote Similarity	NPD6248	Phase 2
0.6009	Remote Similarity	NPD2906	Approved
0.6009	Remote Similarity	NPD6249	Phase 2
0.6008	Remote Similarity	NPD8289	Discontinued
0.6	Remote Similarity	NPD3783	Clinical (unspecified phase)
0.5992	Remote Similarity	NPD4946	Phase 2
0.5991	Remote Similarity	NPD6260	Discontinued
0.5991	Remote Similarity	NPD6206	Phase 1
0.5991	Remote Similarity	NPD3793	Phase 3
0.5991	Remote Similarity	NPD7174	Clinical (unspecified phase)
0.5991	Remote Similarity	NPD7587	Clinical (unspecified phase)
0.599	Remote Similarity	NPD7036	Phase 3
0.599	Remote Similarity	NPD7035	Approved
0.5985	Remote Similarity	NPD7925	Phase 2
0.5985	Remote Similarity	NPD7924	Phase 2
0.5982	Remote Similarity	NPD5042	Phase 1
0.5981	Remote Similarity	NPD5186	Approved
0.5981	Remote Similarity	NPD5183	Approved
0.598	Remote Similarity	NPD7011	Discontinued

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