NPASS Compound

Structure

CID62792 OpenBabel06191715402D 57 65 0 0 1 0 0 0 0 0999 V2000 6.9533 1.5952 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.0955 0.0298 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4155 2.2977 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0869 -3.3482 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7494 -1.7857 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8523 -3.4749 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0310 -1.1987 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5602 -1.8584 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6951 -0.4612 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4630 -0.3181 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2242 0.2315 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7535 -1.7804 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8885 -0.3832 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5104 -0.9153 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8199 0.6737 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0088 -1.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5295 -1.6848 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1688 -0.1767 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0977 0.8276 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3913 -2.5529 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3438 1.8324 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0725 0.4828 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5653 1.1890 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.5578 -2.3624 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.9344 -1.5672 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.9904 -2.5550 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.4176 -1.0429 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0319 -1.9960 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.3613 -1.4956 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.1769 0.2420 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.2940 0.9606 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2880 -1.2891 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0158 0.0002 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.1121 0.9647 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.3605 -2.5604 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.4091 0.2494 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.3537 -0.7635 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.9774 0.9306 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.8253 -2.3564 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.3899 0.7146 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.5842 0.6814 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.9343 -0.3058 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.3538 -1.9868 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.6327 -0.8411 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 3.2888 2.4312 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.6609 2.0175 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.3110 -1.7420 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.9314 2.0484 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8702 -2.9390 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.4833 0.4819 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.8242 -1.2907 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.3843 -1.9485 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.7034 1.0613 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.8023 0.4986 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.6326 -1.9870 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0347 -0.3814 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 22 1 0 0 0 0 2 22 1 0 0 0 0 5 25 1 0 0 0 0 6 39 1 0 0 0 0 7 8 2 0 0 0 0 7 9 1 0 0 0 0 8 12 1 0 0 0 0 9 13 2 0 0 0 0 10 11 1 0 0 0 0 10 14 2 0 0 0 0 11 15 2 0 0 0 0 12 27 2 0 0 0 0 13 27 1 0 0 0 0 14 29 1 0 0 0 0 15 31 1 0 0 0 0 16 17 1 0 0 0 0 18 22 1 0 0 0 0 18 32 1 0 0 0 0 19 23 1 0 0 0 0 19 30 1 0 0 0 0 20 26 1 0 0 0 0 20 39 1 0 0 0 0 21 45 1 0 0 0 0 23 3 1 6 0 0 0 23 34 1 0 0 0 0 24 4 1 1 0 0 0 24 26 1 0 0 0 0 24 28 1 0 0 0 0 25 35 1 0 0 0 0 25 42 1 6 0 0 0 26 16 1 6 0 0 0 27 44 1 0 0 0 0 28 17 1 1 0 0 0 28 29 1 0 0 0 0 29 52 1 6 0 0 0 30 41 1 6 0 0 0 30 42 1 0 0 0 0 31 46 2 0 0 0 0 31 53 1 0 0 0 0 32 47 2 0 0 0 0 32 52 1 0 0 0 0 33 36 1 0 0 0 0 33 37 1 0 0 0 0 33 42 1 1 0 0 0 34 41 1 6 0 0 0 34 53 1 0 0 0 0 35 43 1 1 0 0 0 35 55 1 0 0 0 0 36 40 1 6 0 0 0 36 54 1 0 0 0 0 37 43 1 6 0 0 0 37 56 1 0 0 0 0 38 40 1 6 0 0 0 38 41 1 0 0 0 0 38 48 1 0 0 0 0 39 43 1 6 0 0 0 39 49 1 0 0 0 0 40 21 1 6 0 0 0 40 54 1 0 0 0 0 41 50 1 1 0 0 0 42 57 1 1 0 0 0 43 51 1 1 0 0 0 44 55 1 0 0 0 0 44 56 1 0 0 0 0 44 57 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	794.39
Volume:	788.389
LogP:	4.988
LogD:	3.823
LogS:	-4.2
# Rotatable Bonds:	6
TPSA:	193.97
# H-Bond Aceptor:	13
# H-Bond Donor:	5
# Rings:	10
# Heavy Atoms:	13

MedChem Properties

QED Drug-Likeness Score:	0.215
Synthetic Accessibility Score:	7.921
Fsp3:	0.727
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:	-5.216
MDCK Permeability:	8.737144526094198e-05
Pgp-inhibitor:	1.0
Pgp-substrate:	0.995
Human Intestinal Absorption (HIA):	0.038
20% Bioavailability (F20%):	0.906
30% Bioavailability (F30%):	0.97

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.222
Plasma Protein Binding (PPB):	95.45914459228516%
Volume Distribution (VD):	0.963
Pgp-substrate:	2.420654773712158%

ADMET: Metabolism

CYP1A2-inhibitor:	0.009
CYP1A2-substrate:	0.116
CYP2C19-inhibitor:	0.014
CYP2C19-substrate:	0.384
CYP2C9-inhibitor:	0.19
CYP2C9-substrate:	0.003
CYP2D6-inhibitor:	0.001
CYP2D6-substrate:	0.053
CYP3A4-inhibitor:	0.548
CYP3A4-substrate:	0.521

ADMET: Excretion

Clearance (CL):	3.23
Half-life (T1/2):	0.765

ADMET: Toxicity

hERG Blockers:	0.472
Human Hepatotoxicity (H-HT):	0.966
Drug-inuced Liver Injury (DILI):	0.957
AMES Toxicity:	0.211
Rat Oral Acute Toxicity:	0.909
Maximum Recommended Daily Dose:	0.937
Skin Sensitization:	0.509
Carcinogencity:	0.748
Eye Corrosion:	0.004
Eye Irritation:	0.011
Respiratory Toxicity:	0.985

Download Data

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

Natural Product: NPC62792

Natural Product ID:	NPC62792
*Common Name:**	Rediocide A
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	ZAVYYYQORHVVFN-BDGVIKSFSA-N
Standard InCHI:	InChI=1S/C44H58O13/c1-22(2)18-32(47)52-29-14-10-11-15-31(46)53-34-23(3)19-30-41(34,50)38(48)40(21-45)36(54-40)33-37-43(51,39(6,49)20-26-16-17-28(29)24(26)4)35-25(5)42(30,33)57-44(55-35,56-37)27-12-8-7-9-13-27/h7-15,22-26,28-30,33-38,45,48-51H,16-21H2,1-6H3/b14-10+,15-11+/t23-,24-,25+,26+,28-,29-,30+,33-,34-,35-,36-,37+,38+,39+,40-,41+,42-,43-,44?/m0/s1
SMILES:	OC[C@]12O[C@H]1[C@@H]1[C@]34[C@H]5[C@@]([C@@H]2O)(O)[C@@H](OC(=O)/C=C/C=C/[C@@H]([C@@H]2[C@H]([C@@H](C[C@@]([C@]6([C@@H]1OC(O3)(O[C@H]6[C@H]4C)c1ccccc1)O)(C)O)CC2)C)OC(=O)CC(C)C)[C@H](C5)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL454246
PubChem CID:	44575544
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000147] Macrolides and analogues

*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
NPO17790	Trigonostemon reidioides	Species	Euphorbiaceae	Eukaryota	roots	Rat Buri Province, Thailand	1988-DEC	PMID[14987064]
NPO17790	Trigonostemon reidioides	Species	Euphorbiaceae	Eukaryota	n.a.	root	n.a.	PMID[16204992]
NPO17790	Trigonostemon reidioides	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17790	Trigonostemon reidioides	Species	Euphorbiaceae	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	8
Others	1

Activity Type	# Activity
Cell Line	3
Individual Protein	4
Organism	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT116	Cell Line	HL-60	Homo sapiens	IC50	>	10000.0	nM	PMID[523078]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	10000.0	nM	PMID[523078]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	>	10000.0	nM	PMID[523078]
NPT1814	Individual Protein	Glucagon receptor	Homo sapiens	IC50	=	4.0	nM	PMID[523079]
NPT1110	Individual Protein	C-C chemokine receptor type 6	Homo sapiens	IC50	=	261.0	nM	PMID[523079]
NPT1789	Individual Protein	Alpha-1b adrenergic receptor	Homo sapiens	IC50	=	215.0	nM	PMID[523079]
NPT1788	Individual Protein	Alpha-1a adrenergic receptor	Homo sapiens	IC50	=	13.0	nM	PMID[523079]
NPT2523	Organism	Ctenocephalides felis	Ctenocephalides felis	LD90	=	0.25	ppm	PMID[523077]
NPT2	Others	Unspecified		IC50	=	88.0	nM	PMID[523079]

☑ 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 NPC62792 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	362
0.1-0.2	1318
0.2-0.3	2965
0.3-0.4	6377
0.4-0.5	11822
0.5-0.6	15130
0.6-0.7	3898
0.7-0.8	715
0.8-0.85	71
0.85-0.9	18
0.9-0.95	17
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9859	High Similarity	NPC298072
0.972	High Similarity	NPC478123
0.9437	High Similarity	NPC471139
0.94	High Similarity	NPC478124
0.9324	High Similarity	NPC290683
0.9324	High Similarity	NPC475548
0.9324	High Similarity	NPC475638
0.9267	High Similarity	NPC323356
0.9267	High Similarity	NPC471138
0.9267	High Similarity	NPC326328
0.9267	High Similarity	NPC309991
0.9189	High Similarity	NPC471135
0.9133	High Similarity	NPC322048
0.9133	High Similarity	NPC318447
0.9085	High Similarity	NPC478125
0.9073	High Similarity	NPC319404
0.9067	High Similarity	NPC323001
0.9067	High Similarity	NPC326235
0.8828	High Similarity	NPC325078
0.8784	High Similarity	NPC312393
0.8734	High Similarity	NPC40138
0.8733	High Similarity	NPC476173
0.8701	High Similarity	NPC49297
0.8693	High Similarity	NPC154675
0.8654	High Similarity	NPC275477
0.8636	High Similarity	NPC181924
0.8608	High Similarity	NPC324769
0.8608	High Similarity	NPC477491
0.8608	High Similarity	NPC325732
0.86	High Similarity	NPC327031
0.8535	High Similarity	NPC477188
0.8535	High Similarity	NPC477190
0.8535	High Similarity	NPC43304
0.8491	Intermediate Similarity	NPC61891
0.8462	Intermediate Similarity	NPC476784
0.8447	Intermediate Similarity	NPC477488
0.8442	Intermediate Similarity	NPC146310
0.8421	Intermediate Similarity	NPC76103
0.8421	Intermediate Similarity	NPC474564
0.8411	Intermediate Similarity	NPC478263
0.8375	Intermediate Similarity	NPC473468
0.8375	Intermediate Similarity	NPC475567
0.8375	Intermediate Similarity	NPC473557
0.8366	Intermediate Similarity	NPC70236
0.8366	Intermediate Similarity	NPC476092
0.8366	Intermediate Similarity	NPC475561
0.8366	Intermediate Similarity	NPC475218
0.8366	Intermediate Similarity	NPC475447
0.8366	Intermediate Similarity	NPC475417
0.8365	Intermediate Similarity	NPC322420
0.8365	Intermediate Similarity	NPC66193
0.8344	Intermediate Similarity	NPC478264
0.8323	Intermediate Similarity	NPC472658
0.8323	Intermediate Similarity	NPC475531
0.8323	Intermediate Similarity	NPC475198
0.8323	Intermediate Similarity	NPC472657
0.8323	Intermediate Similarity	NPC475175
0.8313	Intermediate Similarity	NPC471134
0.8312	Intermediate Similarity	NPC96308
0.8289	Intermediate Similarity	NPC240115
0.8278	Intermediate Similarity	NPC34943
0.8269	Intermediate Similarity	NPC471176
0.8269	Intermediate Similarity	NPC469422
0.8194	Intermediate Similarity	NPC469415
0.8176	Intermediate Similarity	NPC477623
0.817	Intermediate Similarity	NPC473602
0.817	Intermediate Similarity	NPC20255
0.8153	Intermediate Similarity	NPC34066
0.8153	Intermediate Similarity	NPC251139
0.8153	Intermediate Similarity	NPC469398
0.8146	Intermediate Similarity	NPC192658
0.8129	Intermediate Similarity	NPC222102
0.8129	Intermediate Similarity	NPC303429
0.8117	Intermediate Similarity	NPC473760
0.8105	Intermediate Similarity	NPC174982
0.8105	Intermediate Similarity	NPC200471
0.8105	Intermediate Similarity	NPC472572
0.8105	Intermediate Similarity	NPC470159
0.8105	Intermediate Similarity	NPC70403
0.8105	Intermediate Similarity	NPC92867
0.8105	Intermediate Similarity	NPC96903
0.8105	Intermediate Similarity	NPC472571
0.8105	Intermediate Similarity	NPC311825
0.8105	Intermediate Similarity	NPC184817
0.8105	Intermediate Similarity	NPC158663
0.8105	Intermediate Similarity	NPC171525
0.8105	Intermediate Similarity	NPC177940
0.8105	Intermediate Similarity	NPC473088
0.8105	Intermediate Similarity	NPC29704
0.8105	Intermediate Similarity	NPC125882
0.8105	Intermediate Similarity	NPC469349
0.8105	Intermediate Similarity	NPC472575
0.8105	Intermediate Similarity	NPC472568
0.8105	Intermediate Similarity	NPC476973
0.8105	Intermediate Similarity	NPC471104
0.8105	Intermediate Similarity	NPC470157
0.8101	Intermediate Similarity	NPC70344
0.8092	Intermediate Similarity	NPC131966
0.8092	Intermediate Similarity	NPC191387
0.8079	Intermediate Similarity	NPC472576
0.8079	Intermediate Similarity	NPC87448
0.8079	Intermediate Similarity	NPC16912
0.8079	Intermediate Similarity	NPC291599
0.8079	Intermediate Similarity	NPC118080
0.8079	Intermediate Similarity	NPC27377
0.8079	Intermediate Similarity	NPC41481
0.8079	Intermediate Similarity	NPC97947
0.8075	Intermediate Similarity	NPC165234
0.8075	Intermediate Similarity	NPC475536
0.8052	Intermediate Similarity	NPC48599
0.8052	Intermediate Similarity	NPC209592
0.8039	Intermediate Similarity	NPC470152
0.8039	Intermediate Similarity	NPC95810
0.8039	Intermediate Similarity	NPC11685
0.8039	Intermediate Similarity	NPC188865
0.8039	Intermediate Similarity	NPC125106
0.8039	Intermediate Similarity	NPC476974
0.8039	Intermediate Similarity	NPC57628
0.8039	Intermediate Similarity	NPC95265
0.8039	Intermediate Similarity	NPC241951
0.8039	Intermediate Similarity	NPC472573
0.8039	Intermediate Similarity	NPC475122
0.8039	Intermediate Similarity	NPC472570
0.8039	Intermediate Similarity	NPC475759
0.8039	Intermediate Similarity	NPC163719
0.8039	Intermediate Similarity	NPC70716
0.8039	Intermediate Similarity	NPC472569
0.8039	Intermediate Similarity	NPC25768
0.8038	Intermediate Similarity	NPC469456
0.8026	Intermediate Similarity	NPC475513
0.8026	Intermediate Similarity	NPC34012
0.8026	Intermediate Similarity	NPC473755
0.8025	Intermediate Similarity	NPC475437
0.8025	Intermediate Similarity	NPC475300
0.8025	Intermediate Similarity	NPC475505
0.8025	Intermediate Similarity	NPC473797
0.8025	Intermediate Similarity	NPC475464
0.8025	Intermediate Similarity	NPC473641
0.8013	Intermediate Similarity	NPC100913
0.8013	Intermediate Similarity	NPC87934
0.8013	Intermediate Similarity	NPC472547
0.8013	Intermediate Similarity	NPC275592
0.8013	Intermediate Similarity	NPC473440
0.8013	Intermediate Similarity	NPC90614
0.8013	Intermediate Similarity	NPC171207
0.8013	Intermediate Similarity	NPC162613
0.8013	Intermediate Similarity	NPC31829
0.8013	Intermediate Similarity	NPC469448
0.8013	Intermediate Similarity	NPC97667
0.8	Intermediate Similarity	NPC58061
0.7987	Intermediate Similarity	NPC472556
0.7974	Intermediate Similarity	NPC91703
0.7974	Intermediate Similarity	NPC163087
0.7961	Intermediate Similarity	NPC266374
0.7949	Intermediate Similarity	NPC471101
0.7949	Intermediate Similarity	NPC266265
0.7949	Intermediate Similarity	NPC270590
0.7949	Intermediate Similarity	NPC301556
0.7949	Intermediate Similarity	NPC476975
0.7949	Intermediate Similarity	NPC92293
0.7947	Intermediate Similarity	NPC9905
0.7935	Intermediate Similarity	NPC474935
0.7931	Intermediate Similarity	NPC476971
0.7931	Intermediate Similarity	NPC476972
0.7925	Intermediate Similarity	NPC132599
0.7925	Intermediate Similarity	NPC473632
0.7925	Intermediate Similarity	NPC473611
0.7925	Intermediate Similarity	NPC469730
0.7917	Intermediate Similarity	NPC284022
0.7914	Intermediate Similarity	NPC269668
0.7911	Intermediate Similarity	NPC469647
0.7911	Intermediate Similarity	NPC22571
0.7911	Intermediate Similarity	NPC283875
0.7911	Intermediate Similarity	NPC138641
0.7911	Intermediate Similarity	NPC469648
0.7911	Intermediate Similarity	NPC233581
0.7911	Intermediate Similarity	NPC145649
0.7908	Intermediate Similarity	NPC63737
0.7907	Intermediate Similarity	NPC186746
0.7905	Intermediate Similarity	NPC476976
0.7898	Intermediate Similarity	NPC470245
0.7898	Intermediate Similarity	NPC473214
0.7888	Intermediate Similarity	NPC469399
0.7885	Intermediate Similarity	NPC281717
0.7881	Intermediate Similarity	NPC39549
0.7875	Intermediate Similarity	NPC11410
0.7871	Intermediate Similarity	NPC251062
0.7871	Intermediate Similarity	NPC184464
0.7862	Intermediate Similarity	NPC470158
0.7862	Intermediate Similarity	NPC469477
0.7862	Intermediate Similarity	NPC475933
0.7862	Intermediate Similarity	NPC133430
0.7862	Intermediate Similarity	NPC476970
0.7857	Intermediate Similarity	NPC477894
0.7848	Intermediate Similarity	NPC470153
0.7843	Intermediate Similarity	NPC224491
0.7838	Intermediate Similarity	NPC476977
0.7834	Intermediate Similarity	NPC473215
0.7829	Intermediate Similarity	NPC473301
0.7815	Intermediate Similarity	NPC472551

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 NPC62792 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	288
0.1-0.2	813
0.2-0.3	1928
0.3-0.4	3384
0.4-0.5	2044
0.5-0.6	591
0.6-0.7	99
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
0.7738	Intermediate Similarity	NPD7799	Discontinued
0.7486	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7421	Intermediate Similarity	NPD7236	Approved
0.7384	Intermediate Similarity	NPD8470	Clinical (unspecified phase)
0.7356	Intermediate Similarity	NPD7685	Pre-registration
0.7329	Intermediate Similarity	NPD5126	Approved
0.7329	Intermediate Similarity	NPD5125	Phase 3
0.7301	Intermediate Similarity	NPD7239	Suspended
0.7215	Intermediate Similarity	NPD7266	Discontinued
0.7192	Intermediate Similarity	NPD7741	Discontinued
0.7161	Intermediate Similarity	NPD7966	Clinical (unspecified phase)
0.7062	Intermediate Similarity	NPD8368	Discontinued
0.7039	Intermediate Similarity	NPD8407	Phase 2
0.7035	Intermediate Similarity	NPD8127	Discontinued
0.7029	Intermediate Similarity	NPD7228	Approved
0.7007	Intermediate Similarity	NPD7516	Approved
0.7	Intermediate Similarity	NPD5762	Approved
0.7	Intermediate Similarity	NPD5763	Approved
0.6993	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6939	Remote Similarity	NPD7327	Approved
0.6939	Remote Similarity	NPD7328	Approved
0.6913	Remote Similarity	NPD8380	Approved
0.6913	Remote Similarity	NPD8335	Approved
0.6913	Remote Similarity	NPD8033	Approved
0.6913	Remote Similarity	NPD8379	Approved
0.6913	Remote Similarity	NPD8378	Approved
0.6913	Remote Similarity	NPD8296	Approved
0.6901	Remote Similarity	NPD7057	Phase 3
0.6901	Remote Similarity	NPD7058	Phase 2
0.6901	Remote Similarity	NPD4965	Approved
0.6901	Remote Similarity	NPD4967	Phase 2
0.6901	Remote Similarity	NPD4966	Approved
0.6872	Remote Similarity	NPD7240	Approved
0.6859	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6846	Remote Similarity	NPD8294	Approved
0.6846	Remote Similarity	NPD8377	Approved
0.6839	Remote Similarity	NPD7199	Phase 2
0.6829	Remote Similarity	NPD7274	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD37	Approved
0.6821	Remote Similarity	NPD6234	Discontinued
0.6807	Remote Similarity	NPD8389	Clinical (unspecified phase)
0.6806	Remote Similarity	NPD7497	Discontinued
0.68	Remote Similarity	NPD7503	Approved
0.6793	Remote Similarity	NPD8361	Approved
0.6793	Remote Similarity	NPD8435	Approved
0.6793	Remote Similarity	NPD8360	Approved
0.6784	Remote Similarity	NPD8455	Phase 2
0.6776	Remote Similarity	NPD8424	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD4198	Discontinued
0.672	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6713	Remote Similarity	NPD6685	Approved
0.6708	Remote Similarity	NPD7097	Phase 1
0.6706	Remote Similarity	NPD7028	Phase 2
0.6703	Remote Similarity	NPD8313	Approved
0.6703	Remote Similarity	NPD8312	Approved
0.6687	Remote Similarity	NPD5735	Approved
0.6685	Remote Similarity	NPD8434	Phase 2
0.6667	Remote Similarity	NPD6663	Approved
0.6667	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6627	Remote Similarity	NPD6190	Approved
0.6624	Remote Similarity	NPD5736	Approved
0.6623	Remote Similarity	NPD7507	Approved
0.6606	Remote Similarity	NPD6674	Discontinued
0.6603	Remote Similarity	NPD7319	Approved
0.6595	Remote Similarity	NPD8150	Discontinued
0.6585	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6585	Remote Similarity	NPD6004	Phase 3
0.6585	Remote Similarity	NPD6005	Phase 3
0.6585	Remote Similarity	NPD6002	Phase 3
0.6585	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6568	Remote Similarity	NPD6273	Approved
0.6566	Remote Similarity	NPD8166	Discontinued
0.6562	Remote Similarity	NPD8486	Clinical (unspecified phase)
0.6556	Remote Similarity	NPD3751	Discontinued
0.6543	Remote Similarity	NPD6653	Approved
0.6522	Remote Similarity	NPD4140	Approved
0.6519	Remote Similarity	NPD5844	Phase 1
0.6517	Remote Similarity	NPD3787	Discontinued
0.6503	Remote Similarity	NPD5765	Approved
0.6497	Remote Similarity	NPD3094	Phase 2
0.6494	Remote Similarity	NPD7457	Clinical (unspecified phase)
0.6491	Remote Similarity	NPD1653	Approved
0.6486	Remote Similarity	NPD6912	Phase 3
0.6486	Remote Similarity	NPD969	Suspended
0.6467	Remote Similarity	NPD2629	Approved
0.646	Remote Similarity	NPD7961	Discontinued
0.6458	Remote Similarity	NPD7699	Phase 2
0.6458	Remote Similarity	NPD7700	Phase 2
0.6443	Remote Similarity	NPD7094	Approved
0.6443	Remote Similarity	NPD6858	Approved
0.6436	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD8319	Approved
0.6429	Remote Similarity	NPD8320	Phase 1
0.6413	Remote Similarity	NPD6559	Discontinued
0.6413	Remote Similarity	NPD6764	Approved
0.6413	Remote Similarity	NPD6765	Approved
0.6406	Remote Similarity	NPD8485	Approved
0.64	Remote Similarity	NPD5760	Phase 2
0.64	Remote Similarity	NPD5761	Phase 2
0.64	Remote Similarity	NPD7819	Suspended
0.6393	Remote Similarity	NPD7074	Phase 3
0.6389	Remote Similarity	NPD5738	Clinical (unspecified phase)
0.6384	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.638	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.638	Remote Similarity	NPD5124	Phase 1
0.638	Remote Similarity	NPD6355	Discontinued
0.6378	Remote Similarity	NPD7680	Approved
0.6369	Remote Similarity	NPD4628	Phase 3
0.6369	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6369	Remote Similarity	NPD7982	Clinical (unspecified phase)
0.6353	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6352	Remote Similarity	NPD6085	Phase 2
0.6352	Remote Similarity	NPD5740	Clinical (unspecified phase)
0.6346	Remote Similarity	NPD3092	Approved
0.6341	Remote Similarity	NPD6353	Approved
0.634	Remote Similarity	NPD7237	Clinical (unspecified phase)
0.6339	Remote Similarity	NPD7054	Approved
0.6328	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6322	Remote Similarity	NPD4380	Phase 2
0.6316	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6313	Remote Similarity	NPD7999	Approved
0.6307	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6304	Remote Similarity	NPD7472	Approved
0.6302	Remote Similarity	NPD6535	Approved
0.6302	Remote Similarity	NPD6534	Approved
0.6296	Remote Similarity	NPD7985	Registered
0.6294	Remote Similarity	NPD7435	Discontinued
0.6292	Remote Similarity	NPD7075	Discontinued
0.629	Remote Similarity	NPD7808	Phase 3
0.6287	Remote Similarity	NPD8462	Phase 1
0.6277	Remote Similarity	NPD6784	Approved
0.6277	Remote Similarity	NPD6785	Approved
0.6276	Remote Similarity	NPD6647	Phase 2
0.6272	Remote Similarity	NPD7488	Clinical (unspecified phase)
0.627	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6264	Remote Similarity	NPD7458	Discontinued
0.6264	Remote Similarity	NPD6591	Clinical (unspecified phase)
0.625	Remote Similarity	NPD5344	Discontinued
0.6237	Remote Similarity	NPD7251	Discontinued
0.6235	Remote Similarity	NPD7008	Discontinued
0.6226	Remote Similarity	NPD7736	Approved
0.6225	Remote Similarity	NPD7930	Approved
0.6222	Remote Similarity	NPD5494	Approved
0.622	Remote Similarity	NPD3620	Phase 2
0.622	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6212	Remote Similarity	NPD7698	Approved
0.6212	Remote Similarity	NPD7697	Approved
0.6212	Remote Similarity	NPD7696	Phase 3
0.6211	Remote Similarity	NPD2861	Phase 2
0.6209	Remote Similarity	NPD7115	Discovery
0.6205	Remote Similarity	NPD4978	Clinical (unspecified phase)
0.6203	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.62	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6199	Remote Similarity	NPD5058	Phase 3
0.6196	Remote Similarity	NPD3818	Discontinued
0.6196	Remote Similarity	NPD3764	Approved
0.6188	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6188	Remote Similarity	NPD6362	Approved
0.6188	Remote Similarity	NPD7874	Approved
0.6184	Remote Similarity	NPD4869	Clinical (unspecified phase)
0.6183	Remote Similarity	NPD6797	Phase 2
0.6181	Remote Similarity	NPD6648	Approved
0.618	Remote Similarity	NPD5402	Approved
0.6171	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6169	Remote Similarity	NPD7701	Phase 2
0.6169	Remote Similarity	NPD4230	Clinical (unspecified phase)
0.6168	Remote Similarity	NPD7033	Discontinued
0.6164	Remote Similarity	NPD7078	Approved
0.6162	Remote Similarity	NPD6823	Phase 2
0.6154	Remote Similarity	NPD2424	Discontinued
0.6149	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6144	Remote Similarity	NPD690	Clinical (unspecified phase)
0.6142	Remote Similarity	NPD6776	Approved
0.6142	Remote Similarity	NPD6779	Approved
0.6142	Remote Similarity	NPD6781	Approved
0.6142	Remote Similarity	NPD6782	Approved
0.6142	Remote Similarity	NPD6780	Approved
0.6142	Remote Similarity	NPD6778	Approved
0.6142	Remote Similarity	NPD6777	Approved
0.6141	Remote Similarity	NPD7473	Discontinued
0.6139	Remote Similarity	NPD7492	Approved
0.6139	Remote Similarity	NPD8151	Discontinued
0.6135	Remote Similarity	NPD7095	Approved
0.6131	Remote Similarity	NPD7137	Phase 2
0.6121	Remote Similarity	NPD4060	Phase 1
0.6118	Remote Similarity	NPD8133	Approved
0.6118	Remote Similarity	NPD5698	Clinical (unspecified phase)
0.6118	Remote Similarity	NPD1652	Phase 2
0.6115	Remote Similarity	NPD3095	Discontinued
0.6111	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6108	Remote Similarity	NPD41	Approved
0.6108	Remote Similarity	NPD5886	Approved
0.6107	Remote Similarity	NPD6686	Approved
0.6101	Remote Similarity	NPD6616	Approved
0.61	Remote Similarity	NPD7870	Phase 2
0.61	Remote Similarity	NPD7871	Phase 2
0.6095	Remote Similarity	NPD7702	Clinical (unspecified phase)
0.609	Remote Similarity	NPD6054	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