NPASS Compound

Structure

CID229505 OpenBabel06191716022D 62 67 0 0 1 0 0 0 0 0999 V2000 0.0570 8.0878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7891 -0.9122 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4071 2.0878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9230 0.5878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6551 -1.4122 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2731 1.5878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9230 1.5878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5411 3.5878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5411 4.5878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6551 0.5878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2731 3.5878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2532 8.0878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0570 2.0878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2226 -1.3578 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3090 -0.9511 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9230 7.5878 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7891 0.0878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4071 3.0878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5211 -0.9122 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1391 2.0878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5211 0.0878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1391 3.0878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1192 7.5878 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0570 3.0878 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7891 2.0878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7891 8.0878 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 6.1192 6.5878 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.6551 7.5878 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.2532 6.0878 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0570 5.0878 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.9230 3.5878 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.9230 4.5878 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.6551 6.5878 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.6180 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.3871 6.5878 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8090 4.5878 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7891 6.0878 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -0.8090 0.5878 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.3090 -0.9511 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.3271 -2.3523 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3871 -1.4122 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0052 1.5878 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3871 0.5878 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0052 3.5878 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.9852 8.0878 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6551 1.5878 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7891 9.0878 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.9852 6.0878 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.5211 8.0878 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.2532 5.0878 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0570 6.0878 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5691 0.3090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.4135 -1.9456 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6750 5.0878 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3871 7.5878 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8090 1.5878 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 0.9230 6.5878 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8090 3.5878 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7891 3.0878 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7891 5.0878 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.5211 6.0878 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 5 2 0 0 0 0 2 17 1 0 0 0 0 3 6 2 0 0 0 0 3 18 1 0 0 0 0 4 7 2 0 0 0 0 4 17 1 0 0 0 0 5 19 1 0 0 0 0 6 20 1 0 0 0 0 7 25 1 0 0 0 0 8 9 1 0 0 0 0 8 18 1 0 0 0 0 9 54 1 0 0 0 0 10 17 2 0 0 0 0 10 21 1 0 0 0 0 11 18 2 0 0 0 0 11 22 1 0 0 0 0 12 23 1 0 0 0 0 12 55 1 0 0 0 0 13 56 1 0 0 0 0 14 39 1 0 0 0 0 14 40 1 0 0 0 0 15 39 1 0 0 0 0 15 57 1 0 0 0 0 16 1 1 1 0 0 0 16 26 1 0 0 0 0 16 58 1 0 0 0 0 19 21 2 0 0 0 0 19 41 1 0 0 0 0 20 22 2 0 0 0 0 20 42 1 0 0 0 0 21 43 1 0 0 0 0 22 44 1 0 0 0 0 23 27 1 0 0 0 0 23 45 1 6 0 0 0 24 13 1 1 0 0 0 24 31 1 0 0 0 0 24 59 1 0 0 0 0 25 46 2 0 0 0 0 25 60 1 0 0 0 0 26 28 1 0 0 0 0 26 47 1 6 0 0 0 27 29 1 0 0 0 0 27 48 1 6 0 0 0 28 33 1 0 0 0 0 28 49 1 1 0 0 0 29 35 1 0 0 0 0 29 50 1 1 0 0 0 30 32 1 0 0 0 0 30 36 1 0 0 0 0 30 51 1 6 0 0 0 31 32 1 0 0 0 0 31 60 1 6 0 0 0 32 61 1 1 0 0 0 33 37 1 0 0 0 0 33 62 1 1 0 0 0 34 38 1 0 0 0 0 34 39 1 1 0 0 0 34 52 1 0 0 0 0 35 55 1 0 0 0 0 35 62 1 6 0 0 0 36 54 1 1 0 0 0 36 59 1 0 0 0 0 37 58 1 0 0 0 0 37 61 1 0 0 0 0 38 56 1 6 0 0 0 38 57 1 0 0 0 0 39 53 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	888.29
Volume:	812.845
LogP:	-0.494
LogD:	-0.393
LogS:	-2.318
# Rotatable Bonds:	16
TPSA:	363.13
# H-Bond Aceptor:	23
# H-Bond Donor:	13
# Rings:	6
# Heavy Atoms:	23

MedChem Properties

QED Drug-Likeness Score:	0.046
Synthetic Accessibility Score:	5.899
Fsp3:	0.615
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.829
MDCK Permeability:	4.542752503766678e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.999
Human Intestinal Absorption (HIA):	0.999
20% Bioavailability (F20%):	0.999
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.139
Plasma Protein Binding (PPB):	82.07263946533203%
Volume Distribution (VD):	-0.039
Pgp-substrate:	14.759893417358398%

ADMET: Metabolism

CYP1A2-inhibitor:	0.01
CYP1A2-substrate:	0.008
CYP2C19-inhibitor:	0.022
CYP2C19-substrate:	0.043
CYP2C9-inhibitor:	0.005
CYP2C9-substrate:	0.034
CYP2D6-inhibitor:	0.003
CYP2D6-substrate:	0.097
CYP3A4-inhibitor:	0.032
CYP3A4-substrate:	0.005

ADMET: Excretion

Clearance (CL):	0.251
Half-life (T1/2):	0.741

ADMET: Toxicity

hERG Blockers:	0.205
Human Hepatotoxicity (H-HT):	0.49
Drug-inuced Liver Injury (DILI):	0.628
AMES Toxicity:	0.268
Rat Oral Acute Toxicity:	0.04
Maximum Recommended Daily Dose:	0.004
Skin Sensitization:	0.97
Carcinogencity:	0.022
Eye Corrosion:	0.003
Eye Irritation:	0.012
Respiratory Toxicity:	0.025

Download Data

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

Natural Product: NPC229505

Natural Product ID:	NPC229505
*Common Name:**	Ballotetroside
IUPAC Name:	[(2R,3R,4R,5R,6R)-2-[[(2R,3R,4R)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxymethyl]-4-[(3R,4R,5R,6S)-4,5-dihydroxy-6-methyl-3-[(2S,3R,4S,5S)-3,4,5-trihydroxyoxan-2-yl]oxyoxan-2-yl]oxy-6-[2-(3,4-dihydroxyphenyl)ethoxy]-5-hydroxyoxan-3-yl] (E)-3-(3,4-dihydroxyphenyl)prop-2-enoate
Synonyms:	Ballotetroside
Standard InCHIKey:	NPVUMVVTBDKDDD-TXEQUVPISA-N
Standard InCHI:	InChI=1S/C39H52O23/c1-16-26(47)28(49)33(62-35-29(50)27(48)23(45)12-55-35)37(58-16)61-32-30(51)36(54-9-8-18-3-6-20(42)22(44)11-18)59-24(13-56-38-34(52)39(53,14-40)15-57-38)31(32)60-25(46)7-4-17-2-5-19(41)21(43)10-17/h2-7,10-11,16,23-24,26-38,40-45,47-53H,8-9,12-15H2,1H3/b7-4+/t16-,23-,24+,26-,27-,28+,29+,30+,31+,32+,33+,34-,35-,36+,37?,38+,39+/m0/s1
SMILES:	OC[C@@]1(O)CO[C@H]([C@@H]1O)OC[C@H]1O[C@@H](OCCc2ccc(c(c2)O)O)[C@@H]([C@H]([C@@H]1OC(=O)/C=C/c1ccc(c(c1)O)O)OC1O[C@@H](C)[C@@H]([C@H]([C@H]1O[C@@H]1OC[C@@H]([C@@H]([C@H]1O)O)O)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL449150
PubChem CID:	44584314
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0000011] Carbohydrates and carbohydrate conjugates [CHEMONTID:0000198] Oligosaccharides

*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
NPO23264	Marrubium vulgare	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO23264	Marrubium vulgare	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23264	Marrubium vulgare	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO23264	Marrubium vulgare	Species	Lamiaceae	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	1

Activity Type	# Activity
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT30	Individual Protein	Cyclooxygenase-1	Homo sapiens	IC50	=	1000000.0	nM	PMID[543069]

☑ 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 NPC229505 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	314
0.1-0.2	1306
0.2-0.3	2990
0.3-0.4	6975
0.4-0.5	9938
0.5-0.6	10569
0.6-0.7	7648
0.7-0.8	2632
0.8-0.85	193
0.85-0.9	65
0.9-0.95	42
0.95-1	25

Similarity Score	Similarity Level	Natural Product ID
0.9855	High Similarity	NPC196063
0.9855	High Similarity	NPC300894
0.9855	High Similarity	NPC141455
0.9855	High Similarity	NPC296954
0.9783	High Similarity	NPC175214
0.9783	High Similarity	NPC298257
0.9783	High Similarity	NPC247032
0.9783	High Similarity	NPC96795
0.9783	High Similarity	NPC269141
0.9783	High Similarity	NPC476384
0.9783	High Similarity	NPC119537
0.9783	High Similarity	NPC105005
0.9783	High Similarity	NPC76406
0.9783	High Similarity	NPC476380
0.9783	High Similarity	NPC476381
0.9783	High Similarity	NPC476375
0.9783	High Similarity	NPC476378
0.9783	High Similarity	NPC112
0.9783	High Similarity	NPC205864
0.9783	High Similarity	NPC264632
0.9783	High Similarity	NPC476397
0.9712	High Similarity	NPC64195
0.9638	High Similarity	NPC47471
0.9638	High Similarity	NPC476377
0.9568	High Similarity	NPC265648
0.9568	High Similarity	NPC222433
0.9565	High Similarity	NPC475530
0.9565	High Similarity	NPC473799
0.95	High Similarity	NPC40305
0.9496	High Similarity	NPC476385
0.9496	High Similarity	NPC134405
0.9493	High Similarity	NPC321638
0.9493	High Similarity	NPC64141
0.9493	High Similarity	NPC81515
0.9493	High Similarity	NPC321184
0.9493	High Similarity	NPC472350
0.9493	High Similarity	NPC205195
0.9493	High Similarity	NPC476383
0.9493	High Similarity	NPC89105
0.9493	High Similarity	NPC328273
0.9493	High Similarity	NPC197316
0.9493	High Similarity	NPC171134
0.9493	High Similarity	NPC68092
0.9444	High Similarity	NPC188393
0.9444	High Similarity	NPC470934
0.942	High Similarity	NPC260425
0.942	High Similarity	NPC476376
0.9375	High Similarity	NPC259347
0.9375	High Similarity	NPC470933
0.9375	High Similarity	NPC476398
0.9375	High Similarity	NPC473427
0.9375	High Similarity	NPC471062
0.9375	High Similarity	NPC94871
0.9375	High Similarity	NPC476386
0.9375	High Similarity	NPC306890
0.931	High Similarity	NPC257970
0.931	High Similarity	NPC470927
0.9281	High Similarity	NPC78363
0.9275	High Similarity	NPC263829
0.9236	High Similarity	NPC232992
0.9203	High Similarity	NPC287597
0.9203	High Similarity	NPC34293
0.9203	High Similarity	NPC471883
0.9203	High Similarity	NPC886
0.9184	High Similarity	NPC106818
0.913	High Similarity	NPC254398
0.9122	High Similarity	NPC87403
0.9097	High Similarity	NPC252292
0.9097	High Similarity	NPC34587
0.9097	High Similarity	NPC476382
0.9097	High Similarity	NPC262182
0.9097	High Similarity	NPC216819
0.9097	High Similarity	NPC34927
0.9097	High Similarity	NPC100998
0.9097	High Similarity	NPC83743
0.9097	High Similarity	NPC287615
0.9058	High Similarity	NPC473924
0.9058	High Similarity	NPC473285
0.9041	High Similarity	NPC300262
0.9041	High Similarity	NPC3460
0.9041	High Similarity	NPC80732
0.9041	High Similarity	NPC261122
0.9041	High Similarity	NPC210611
0.9041	High Similarity	NPC201148
0.9041	High Similarity	NPC199311
0.9041	High Similarity	NPC192763
0.9041	High Similarity	NPC215095
0.9041	High Similarity	NPC28651
0.9028	High Similarity	NPC110063
0.9	High Similarity	NPC476870
0.8986	High Similarity	NPC85192
0.8986	High Similarity	NPC125823
0.8986	High Similarity	NPC46137
0.8986	High Similarity	NPC7145
0.8986	High Similarity	NPC478255
0.8986	High Similarity	NPC143480
0.8986	High Similarity	NPC235294
0.8986	High Similarity	NPC219677
0.8926	High Similarity	NPC478268
0.8912	High Similarity	NPC23677
0.8904	High Similarity	NPC476865
0.8897	High Similarity	NPC476867
0.8889	High Similarity	NPC140502
0.8867	High Similarity	NPC471874
0.8857	High Similarity	NPC28637
0.8851	High Similarity	NPC90896
0.8851	High Similarity	NPC283839
0.8849	High Similarity	NPC246869
0.8849	High Similarity	NPC225384
0.8849	High Similarity	NPC138777
0.8841	High Similarity	NPC229784
0.8841	High Similarity	NPC477293
0.8841	High Similarity	NPC477294
0.8836	High Similarity	NPC476868
0.8836	High Similarity	NPC476866
0.8836	High Similarity	NPC476869
0.8836	High Similarity	NPC476864
0.88	High Similarity	NPC472611
0.88	High Similarity	NPC289967
0.88	High Similarity	NPC472612
0.8792	High Similarity	NPC476871
0.8786	High Similarity	NPC254275
0.8774	High Similarity	NPC246024
0.8768	High Similarity	NPC232880
0.8768	High Similarity	NPC225307
0.871	High Similarity	NPC149873
0.871	High Similarity	NPC7191
0.8705	High Similarity	NPC184092
0.8699	High Similarity	NPC478239
0.8696	High Similarity	NPC45224
0.8696	High Similarity	NPC476873
0.8696	High Similarity	NPC35288
0.8696	High Similarity	NPC288416
0.8696	High Similarity	NPC103533
0.8696	High Similarity	NPC156692
0.8696	High Similarity	NPC471882
0.8696	High Similarity	NPC173150
0.8696	High Similarity	NPC106677
0.8696	High Similarity	NPC471881
0.8693	High Similarity	NPC11411
0.869	High Similarity	NPC186406
0.8681	High Similarity	NPC220942
0.8681	High Similarity	NPC226005
0.8671	High Similarity	NPC470572
0.8667	High Similarity	NPC69367
0.8658	High Similarity	NPC28776
0.8658	High Similarity	NPC473138
0.863	High Similarity	NPC296643
0.863	High Similarity	NPC157816
0.8623	High Similarity	NPC61181
0.8623	High Similarity	NPC471157
0.86	High Similarity	NPC106138
0.86	High Similarity	NPC478242
0.8581	High Similarity	NPC478269
0.8571	High Similarity	NPC278961
0.8571	High Similarity	NPC113680
0.8561	High Similarity	NPC264900
0.8561	High Similarity	NPC79715
0.8561	High Similarity	NPC108659
0.8561	High Similarity	NPC231607
0.8551	High Similarity	NPC83218
0.8551	High Similarity	NPC90318
0.8551	High Similarity	NPC126991
0.8543	High Similarity	NPC475224
0.8542	High Similarity	NPC154485
0.8542	High Similarity	NPC471872
0.8542	High Similarity	NPC157554
0.8526	High Similarity	NPC478265
0.8523	High Similarity	NPC199928
0.8516	High Similarity	NPC226759
0.8514	High Similarity	NPC232228
0.8514	High Similarity	NPC297342
0.8514	High Similarity	NPC292443
0.8503	High Similarity	NPC473873
0.8503	High Similarity	NPC473792
0.8493	Intermediate Similarity	NPC202700
0.8491	Intermediate Similarity	NPC59516
0.8489	Intermediate Similarity	NPC94179
0.8472	Intermediate Similarity	NPC123988
0.8471	Intermediate Similarity	NPC478267
0.8452	Intermediate Similarity	NPC478266
0.8446	Intermediate Similarity	NPC46092
0.8435	Intermediate Similarity	NPC472711
0.8425	Intermediate Similarity	NPC100389
0.8418	Intermediate Similarity	NPC471873
0.8414	Intermediate Similarity	NPC52277
0.8414	Intermediate Similarity	NPC177035
0.8414	Intermediate Similarity	NPC199459
0.8408	Intermediate Similarity	NPC269668
0.8403	Intermediate Similarity	NPC135127
0.8403	Intermediate Similarity	NPC470881
0.8403	Intermediate Similarity	NPC35731
0.84	Intermediate Similarity	NPC473867
0.84	Intermediate Similarity	NPC320734
0.8397	Intermediate Similarity	NPC471878
0.8397	Intermediate Similarity	NPC187205
0.8389	Intermediate Similarity	NPC84181
0.8389	Intermediate Similarity	NPC470235
0.8389	Intermediate Similarity	NPC129417
0.8389	Intermediate Similarity	NPC283995

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 NPC229505 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	250
0.1-0.2	766
0.2-0.3	1651
0.3-0.4	2984
0.4-0.5	2118
0.5-0.6	1089
0.6-0.7	264
0.7-0.8	27
0.8-0.85	0
0.85-0.9	0
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9493	High Similarity	NPD7266	Discontinued
0.7961	Intermediate Similarity	NPD6190	Approved
0.7904	Intermediate Similarity	NPD7685	Pre-registration
0.7885	Intermediate Similarity	NPD1653	Approved
0.7879	Intermediate Similarity	NPD7228	Approved
0.7784	Intermediate Similarity	NPD7472	Approved
0.7784	Intermediate Similarity	NPD7074	Phase 3
0.7725	Intermediate Similarity	NPD7054	Approved
0.7692	Intermediate Similarity	NPD7251	Discontinued
0.7647	Intermediate Similarity	NPD7808	Phase 3
0.7633	Intermediate Similarity	NPD6797	Phase 2
0.7616	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7531	Intermediate Similarity	NPD8455	Phase 2
0.7516	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD7240	Approved
0.7456	Intermediate Similarity	NPD3818	Discontinued
0.7455	Intermediate Similarity	NPD6234	Discontinued
0.745	Intermediate Similarity	NPD3027	Phase 3
0.7436	Intermediate Similarity	NPD8166	Discontinued
0.7362	Intermediate Similarity	NPD37	Approved
0.7341	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD4965	Approved
0.7333	Intermediate Similarity	NPD4967	Phase 2
0.7333	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD4966	Approved
0.7326	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD1613	Approved
0.7303	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7299	Intermediate Similarity	NPD8312	Approved
0.7299	Intermediate Similarity	NPD8313	Approved
0.7209	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7186	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7184	Intermediate Similarity	NPD6559	Discontinued
0.7162	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD6674	Discontinued
0.7143	Intermediate Similarity	NPD3705	Approved
0.7143	Intermediate Similarity	NPD230	Phase 1
0.7135	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD6166	Phase 2
0.7111	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD7680	Approved
0.7095	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7065	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD7199	Phase 2
0.7055	Intermediate Similarity	NPD1357	Approved
0.7051	Intermediate Similarity	NPD7097	Phase 1
0.7039	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD1091	Approved
0.7019	Intermediate Similarity	NPD5058	Phase 3
0.7007	Intermediate Similarity	NPD5126	Approved
0.7007	Intermediate Similarity	NPD5125	Phase 3
0.6974	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD8127	Discontinued
0.695	Remote Similarity	NPD3021	Approved
0.695	Remote Similarity	NPD3022	Approved
0.6948	Remote Similarity	NPD3764	Approved
0.6946	Remote Similarity	NPD1934	Approved
0.6943	Remote Similarity	NPD4978	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD2978	Approved
0.6905	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD2977	Approved
0.6894	Remote Similarity	NPD4628	Phase 3
0.6879	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6878	Remote Similarity	NPD8319	Approved
0.6878	Remote Similarity	NPD8320	Phase 1
0.6867	Remote Similarity	NPD3455	Phase 2
0.6859	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6853	Remote Similarity	NPD969	Suspended
0.6826	Remote Similarity	NPD4380	Phase 2
0.6824	Remote Similarity	NPD3882	Suspended
0.6818	Remote Similarity	NPD5844	Phase 1
0.6813	Remote Similarity	NPD2029	Clinical (unspecified phase)
0.6805	Remote Similarity	NPD1465	Phase 2
0.6796	Remote Similarity	NPD8150	Discontinued
0.6784	Remote Similarity	NPD7075	Discontinued
0.6774	Remote Similarity	NPD7095	Approved
0.6765	Remote Similarity	NPD3817	Phase 2
0.6761	Remote Similarity	NPD3751	Discontinued
0.6753	Remote Similarity	NPD2861	Phase 2
0.6752	Remote Similarity	NPD4060	Phase 1
0.6738	Remote Similarity	NPD7700	Phase 2
0.6738	Remote Similarity	NPD7699	Phase 2
0.6736	Remote Similarity	NPD228	Approved
0.6736	Remote Similarity	NPD8151	Discontinued
0.6728	Remote Similarity	NPD1652	Phase 2
0.6709	Remote Similarity	NPD4340	Discontinued
0.6709	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6709	Remote Similarity	NPD5124	Phase 1
0.6706	Remote Similarity	NPD2801	Approved
0.6689	Remote Similarity	NPD5536	Phase 2
0.6688	Remote Similarity	NPD6233	Phase 2
0.6685	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7783	Phase 2
0.6667	Remote Similarity	NPD7458	Discontinued
0.6667	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5402	Approved
0.6667	Remote Similarity	NPD7549	Discontinued
0.6667	Remote Similarity	NPD6653	Approved
0.6649	Remote Similarity	NPD7435	Discontinued
0.6647	Remote Similarity	NPD7945	Clinical (unspecified phase)
0.6646	Remote Similarity	NPD3620	Phase 2
0.6646	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6645	Remote Similarity	NPD5736	Approved
0.6644	Remote Similarity	NPD9545	Approved
0.6629	Remote Similarity	NPD3787	Discontinued
0.6627	Remote Similarity	NPD4160	Clinical (unspecified phase)
0.6627	Remote Similarity	NPD7028	Phase 2
0.6627	Remote Similarity	NPD8389	Clinical (unspecified phase)
0.6623	Remote Similarity	NPD3094	Phase 2
0.6612	Remote Similarity	NPD8434	Phase 2
0.6609	Remote Similarity	NPD5494	Approved
0.6608	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6608	Remote Similarity	NPD7819	Suspended
0.6605	Remote Similarity	NPD5763	Approved
0.6605	Remote Similarity	NPD5762	Approved
0.6604	Remote Similarity	NPD6355	Discontinued
0.6603	Remote Similarity	NPD4908	Phase 1
0.659	Remote Similarity	NPD7975	Clinical (unspecified phase)
0.6587	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.6584	Remote Similarity	NPD5588	Approved
0.6584	Remote Similarity	NPD7033	Discontinued
0.6578	Remote Similarity	NPD6535	Approved
0.6578	Remote Similarity	NPD6534	Approved
0.6575	Remote Similarity	NPD7843	Approved
0.6573	Remote Similarity	NPD1358	Approved
0.6566	Remote Similarity	NPD1511	Approved
0.6562	Remote Similarity	NPD7698	Approved
0.6562	Remote Similarity	NPD7696	Phase 3
0.6562	Remote Similarity	NPD5314	Approved
0.6562	Remote Similarity	NPD7697	Approved
0.6548	Remote Similarity	NPD5403	Approved
0.6543	Remote Similarity	NPD2935	Discontinued
0.6541	Remote Similarity	NPD3062	Approved
0.6541	Remote Similarity	NPD3059	Approved
0.6541	Remote Similarity	NPD3061	Approved
0.6536	Remote Similarity	NPD8470	Clinical (unspecified phase)
0.6536	Remote Similarity	NPD9269	Phase 2
0.6534	Remote Similarity	NPD6232	Discontinued
0.6531	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6531	Remote Similarity	NPD7874	Approved
0.6531	Remote Similarity	NPD5283	Phase 1
0.6527	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6524	Remote Similarity	NPD5698	Clinical (unspecified phase)
0.6524	Remote Similarity	NPD4237	Approved
0.6524	Remote Similarity	NPD4236	Phase 3
0.6522	Remote Similarity	NPD4537	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD4536	Approved
0.6522	Remote Similarity	NPD4538	Approved
0.6519	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6519	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6519	Remote Similarity	NPD6798	Discontinued
0.6517	Remote Similarity	NPD7473	Discontinued
0.6513	Remote Similarity	NPD7701	Phase 2
0.6513	Remote Similarity	NPD3496	Discontinued
0.6512	Remote Similarity	NPD5563	Clinical (unspecified phase)
0.651	Remote Similarity	NPD6823	Phase 2
0.6509	Remote Similarity	NPD3686	Approved
0.6509	Remote Similarity	NPD3687	Approved
0.65	Remote Similarity	NPD1933	Approved
0.6495	Remote Similarity	NPD7999	Approved
0.6494	Remote Similarity	NPD2983	Phase 2
0.6494	Remote Similarity	NPD2982	Phase 2
0.6492	Remote Similarity	NPD6780	Approved
0.6492	Remote Similarity	NPD6782	Approved
0.6492	Remote Similarity	NPD6778	Approved
0.6492	Remote Similarity	NPD6779	Approved
0.6492	Remote Similarity	NPD6781	Approved
0.6492	Remote Similarity	NPD6777	Approved
0.6492	Remote Similarity	NPD6776	Approved
0.6491	Remote Similarity	NPD6385	Approved
0.6491	Remote Similarity	NPD6386	Approved
0.6488	Remote Similarity	NPD1512	Approved
0.6486	Remote Similarity	NPD6841	Approved
0.6486	Remote Similarity	NPD6842	Approved
0.6486	Remote Similarity	NPD6843	Phase 3
0.6485	Remote Similarity	NPD4110	Phase 3
0.6485	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6485	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.648	Remote Similarity	NPD7799	Discontinued
0.6478	Remote Similarity	NPD6663	Approved
0.6471	Remote Similarity	NPD3092	Approved
0.6471	Remote Similarity	NPD422	Phase 1
0.6467	Remote Similarity	NPD4357	Discontinued
0.6463	Remote Similarity	NPD2424	Discontinued
0.6456	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6453	Remote Similarity	NPD6801	Discontinued
0.6447	Remote Similarity	NPD9384	Approved
0.6447	Remote Similarity	NPD9381	Approved
0.6443	Remote Similarity	NPD7871	Phase 2
0.6443	Remote Similarity	NPD7870	Phase 2
0.6443	Remote Similarity	NPD7157	Approved
0.6442	Remote Similarity	NPD9570	Approved
0.6438	Remote Similarity	NPD4140	Approved
0.6438	Remote Similarity	NPD943	Approved
0.6438	Remote Similarity	NPD825	Approved
0.6438	Remote Similarity	NPD826	Approved
0.6438	Remote Similarity	NPD1558	Phase 1
0.6437	Remote Similarity	NPD7768	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