NPASS Compound

Structure

NPC226153 OpenBabel07101718242D 51 56 0 0 1 0 0 0 0 0999 V2000 1.5522 2.0704 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5759 2.5227 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5116 -3.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4662 -1.3975 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1097 -7.5933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2437 -0.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8839 -2.1020 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1097 -4.5933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.4497 -1.7111 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7796 -1.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2514 1.4476 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1097 -5.5933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.8565 -2.6247 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6456 -1.5933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2460 1.3431 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3776 -4.5933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8674 -2.4156 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6456 0.4067 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0704 -0.2749 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.6106 -4.9118 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8090 1.4013 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.1691 1.6092 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.3776 -2.5933 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.0540 -0.5885 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.2437 -4.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4552 -1.6066 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7796 -0.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6637 0.6386 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3776 -5.5933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2437 -6.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.2687 -3.4337 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5116 -1.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6527 0.4296 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5116 -0.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0649 -0.3795 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.2742 -3.3292 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2437 -3.0933 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.0485 -0.6930 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.9135 0.4067 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.6691 0.7431 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.5116 -6.0933 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.1097 -2.5933 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.6363 0.1160 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.2437 -7.0933 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3776 0.4067 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4716 -1.2930 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.4766 -4.4118 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.8674 -4.2427 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3776 -1.5933 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.6472 0.3250 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 5 44 1 0 0 0 0 6 45 1 0 0 0 0 7 46 1 0 0 0 0 8 12 2 0 0 0 0 8 25 1 0 0 0 0 9 13 2 0 0 0 0 9 26 1 0 0 0 0 10 14 2 0 0 0 0 10 27 1 0 0 0 0 11 15 2 0 0 0 0 11 28 1 0 0 0 0 12 30 1 0 0 0 0 13 31 1 0 0 0 0 14 32 1 0 0 0 0 15 33 1 0 0 0 0 16 25 2 0 0 0 0 16 29 1 0 0 0 0 17 26 2 0 0 0 0 17 36 1 0 0 0 0 18 27 2 0 0 0 0 18 34 1 0 0 0 0 19 28 2 0 0 0 0 19 35 1 0 0 0 0 20 47 1 0 0 0 0 20 48 1 0 0 0 0 21 1 1 1 0 0 0 21 22 1 0 0 0 0 21 39 1 0 0 0 0 22 2 1 6 0 0 0 22 40 1 0 0 0 0 23 3 1 1 0 0 0 23 37 1 0 0 0 0 23 49 1 0 0 0 0 24 4 1 6 0 0 0 24 38 1 0 0 0 0 24 50 1 0 0 0 0 25 37 1 0 0 0 0 26 38 1 0 0 0 0 29 30 2 0 0 0 0 29 41 1 0 0 0 0 30 44 1 0 0 0 0 31 36 2 0 0 0 0 31 47 1 0 0 0 0 32 34 2 0 0 0 0 32 49 1 0 0 0 0 33 35 2 0 0 0 0 33 50 1 0 0 0 0 34 45 1 0 0 0 0 35 46 1 0 0 0 0 36 48 1 0 0 0 0 37 42 1 6 0 0 0 38 43 1 1 0 0 0 39 27 1 1 0 0 0 39 51 1 0 0 0 0 40 28 1 6 0 0 0 40 51 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	702.3
Volume:	714.112
LogP:	6.423
LogD:	4.566
LogS:	-5.915
# Rotatable Bonds:	13
TPSA:	134.53
# H-Bond Aceptor:	11
# H-Bond Donor:	3
# Rings:	6
# Heavy Atoms:	11

MedChem Properties

QED Drug-Likeness Score:	0.13
Synthetic Accessibility Score:	4.661
Fsp3:	0.4
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.438
MDCK Permeability:	3.821739664999768e-05
Pgp-inhibitor:	0.999
Pgp-substrate:	0.359
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.0
30% Bioavailability (F30%):	0.005

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.003
Plasma Protein Binding (PPB):	90.40206146240234%
Volume Distribution (VD):	0.427
Pgp-substrate:	4.1080121994018555%

ADMET: Metabolism

CYP1A2-inhibitor:	0.034
CYP1A2-substrate:	0.954
CYP2C19-inhibitor:	0.87
CYP2C19-substrate:	0.63
CYP2C9-inhibitor:	0.931
CYP2C9-substrate:	0.946
CYP2D6-inhibitor:	0.88
CYP2D6-substrate:	0.948
CYP3A4-inhibitor:	0.975
CYP3A4-substrate:	0.93

ADMET: Excretion

Clearance (CL):	7.373
Half-life (T1/2):	0.068

ADMET: Toxicity

hERG Blockers:	0.235
Human Hepatotoxicity (H-HT):	0.089
Drug-inuced Liver Injury (DILI):	0.932
AMES Toxicity:	0.06
Rat Oral Acute Toxicity:	0.055
Maximum Recommended Daily Dose:	0.055
Skin Sensitization:	0.157
Carcinogencity:	0.164
Eye Corrosion:	0.003
Eye Irritation:	0.015
Respiratory Toxicity:	0.01

Download Data

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

Natural Product: NPC226153

Natural Product ID:	NPC226153
*Common Name:**	3''-O-Demethylmanassantin B
IUPAC Name:	5-[(1R,2R)-2-[4-[(2S,3R,4R,5S)-5-[4-[(1R,2R)-1-(1,3-benzodioxol-5-yl)-1-hydroxypropan-2-yl]oxy-3-methoxyphenyl]-3,4-dimethyloxolan-2-yl]-2-methoxyphenoxy]-1-hydroxypropyl]-2-methoxyphenol
Synonyms:
Standard InCHIKey:	XERBFZDXUVVXOL-NPIUFYBCSA-N
Standard InCHI:	InChI=1S/C40H46O11/c1-21-22(2)40(28-11-15-33(35(19-28)46-7)50-24(4)38(43)26-9-13-31-36(17-26)48-20-47-31)51-39(21)27-10-14-32(34(18-27)45-6)49-23(3)37(42)25-8-12-30(44-5)29(41)16-25/h8-19,21-24,37-43H,20H2,1-7H3/t21-,22-,23-,24-,37+,38+,39+,40+/m1/s1
SMILES:	COc1cc(ccc1O[C@@H]([C@@H](c1ccc(c(c1)O)OC)O)C)[C@H]1O[C@@H]([C@@H]([C@H]1C)C)c1ccc(c(c1)OC)O[C@@H]([C@@H](c1ccc2c(c1)OCO2)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3105549
PubChem CID:	73890953
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0001392] Lignans, neolignans and related compounds [CHEMONTID:0003686] Furanoid lignans [CHEMONTID:0001604] Tetrahydrofuran lignans [CHEMONTID:0003423] 7,7'-epoxylignans

*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
NPO20323	Saururus chinensis	Species	Saururaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10924192]
NPO20323	Saururus chinensis	Species	Saururaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11754613]
NPO20323	Saururus chinensis	Species	Saururaceae	Eukaryota	n.a.	root	n.a.	PMID[14750033]
NPO20323	Saururus chinensis	Species	Saururaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15482936]
NPO20323	Saururus chinensis	Species	Saururaceae	Eukaryota	roots	n.a.	n.a.	PMID[18841903]
NPO20323	Saururus chinensis	Species	Saururaceae	Eukaryota	Roots	n.a.	n.a.	PMID[24359277]
NPO20323	Saururus chinensis	Species	Saururaceae	Eukaryota	Aerial Parts	n.a.	n.a.	PMID[24387347]
NPO20323	Saururus chinensis	Species	Saururaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31642320]
NPO20323	Saururus chinensis	Species	Saururaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO20323	Saururus chinensis	Species	Saururaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20323	Saururus chinensis	Species	Saururaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO20323	Saururus chinensis	Species	Saururaceae	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
EC50	1
Others	2

Activity Type	# Activity
Organism	1
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified		Ratio CC50/EC50	=	20.2	n.a.	PMID[525269]
NPT27	Others	Unspecified		CC50	=	26500.0	nM	PMID[525269]
NPT164	Organism	Human herpesvirus 4	Human herpesvirus 4	EC50	=	2690.0	nM	PMID[525269]

☑ 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 NPC226153 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	430
0.1-0.2	1376
0.2-0.3	3500
0.3-0.4	9352
0.4-0.5	9651
0.5-0.6	5792
0.6-0.7	8249
0.7-0.8	3425
0.8-0.85	653
0.85-0.9	234
0.9-0.95	29
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC304048
0.9857	High Similarity	NPC241846
0.9857	High Similarity	NPC93610
0.9571	High Similarity	NPC302506
0.95	High Similarity	NPC470372
0.9437	High Similarity	NPC179521
0.9375	High Similarity	NPC99183
0.9371	High Similarity	NPC38041
0.9371	High Similarity	NPC279298
0.9371	High Similarity	NPC22150
0.9357	High Similarity	NPC260842
0.9315	High Similarity	NPC475224
0.9306	High Similarity	NPC112861
0.9247	High Similarity	NPC473266
0.9247	High Similarity	NPC470826
0.9247	High Similarity	NPC470098
0.9236	High Similarity	NPC18979
0.9231	High Similarity	NPC477898
0.9231	High Similarity	NPC470950
0.9231	High Similarity	NPC185307
0.9214	High Similarity	NPC77861
0.9211	High Similarity	NPC7191
0.9211	High Similarity	NPC149873
0.92	High Similarity	NPC11411
0.9172	High Similarity	NPC276753
0.9172	High Similarity	NPC205796
0.9167	High Similarity	NPC283995
0.9167	High Similarity	NPC470235
0.9167	High Similarity	NPC84181
0.9167	High Similarity	NPC129417
0.9161	High Similarity	NPC476356
0.9161	High Similarity	NPC246947
0.9155	High Similarity	NPC55793
0.9143	High Similarity	NPC142547
0.9143	High Similarity	NPC135777
0.9143	High Similarity	NPC93783
0.9122	High Similarity	NPC321972
0.9122	High Similarity	NPC329343
0.9122	High Similarity	NPC324517
0.9116	High Similarity	NPC51328
0.9116	High Similarity	NPC286235
0.9116	High Similarity	NPC55158
0.9097	High Similarity	NPC46092
0.9091	High Similarity	NPC472711
0.9054	High Similarity	NPC98624
0.9048	High Similarity	NPC248132
0.9048	High Similarity	NPC130449
0.9034	High Similarity	NPC471063
0.9034	High Similarity	NPC471415
0.9034	High Similarity	NPC470097
0.9034	High Similarity	NPC114119
0.898	High Similarity	NPC193473
0.898	High Similarity	NPC39657
0.898	High Similarity	NPC15956
0.898	High Similarity	NPC328567
0.898	High Similarity	NPC327412
0.898	High Similarity	NPC320671
0.898	High Similarity	NPC275284
0.898	High Similarity	NPC224674
0.898	High Similarity	NPC320970
0.898	High Similarity	NPC213074
0.898	High Similarity	NPC114505
0.898	High Similarity	NPC31325
0.8974	High Similarity	NPC59516
0.8973	High Similarity	NPC469586
0.8966	High Similarity	NPC278961
0.8966	High Similarity	NPC113680
0.8951	High Similarity	NPC156376
0.8951	High Similarity	NPC193666
0.8951	High Similarity	NPC123526
0.8951	High Similarity	NPC88640
0.8933	High Similarity	NPC478268
0.8929	High Similarity	NPC106739
0.8929	High Similarity	NPC259742
0.8929	High Similarity	NPC104077
0.8929	High Similarity	NPC147616
0.8929	High Similarity	NPC471505
0.8929	High Similarity	NPC219671
0.8912	High Similarity	NPC324492
0.8912	High Similarity	NPC317053
0.8889	High Similarity	NPC106944
0.8881	High Similarity	NPC470413
0.8881	High Similarity	NPC138738
0.8873	High Similarity	NPC184938
0.8873	High Similarity	NPC101624
0.8865	High Similarity	NPC169973
0.8859	High Similarity	NPC35877
0.8859	High Similarity	NPC95392
0.8859	High Similarity	NPC55715
0.8859	High Similarity	NPC44452
0.8844	High Similarity	NPC43508
0.8844	High Similarity	NPC476301
0.8844	High Similarity	NPC286245
0.8844	High Similarity	NPC272619
0.8831	High Similarity	NPC478269
0.8828	High Similarity	NPC471908
0.8811	High Similarity	NPC199459
0.8811	High Similarity	NPC177035
0.8811	High Similarity	NPC52277
0.8776	High Similarity	NPC471667
0.8776	High Similarity	NPC472712
0.8776	High Similarity	NPC187774
0.8776	High Similarity	NPC238216
0.8776	High Similarity	NPC217635
0.8776	High Similarity	NPC84684
0.8776	High Similarity	NPC253015
0.8776	High Similarity	NPC79429
0.8776	High Similarity	NPC473046
0.8776	High Similarity	NPC208994
0.8776	High Similarity	NPC185388
0.8776	High Similarity	NPC471065
0.8776	High Similarity	NPC118385
0.8776	High Similarity	NPC472713
0.8767	High Similarity	NPC253878
0.8759	High Similarity	NPC291101
0.8759	High Similarity	NPC266197
0.8759	High Similarity	NPC177868
0.875	High Similarity	NPC115203
0.8741	High Similarity	NPC18576
0.8723	High Similarity	NPC27843
0.8723	High Similarity	NPC476345
0.8723	High Similarity	NPC7171
0.8723	High Similarity	NPC115207
0.8723	High Similarity	NPC228346
0.8723	High Similarity	NPC158079
0.8723	High Similarity	NPC161557
0.8723	High Similarity	NPC40432
0.8718	High Similarity	NPC478267
0.8716	High Similarity	NPC473909
0.8716	High Similarity	NPC274960
0.8716	High Similarity	NPC143120
0.8707	High Similarity	NPC185071
0.8707	High Similarity	NPC12728
0.8707	High Similarity	NPC255566
0.8707	High Similarity	NPC298317
0.8707	High Similarity	NPC265154
0.8699	High Similarity	NPC471414
0.8693	High Similarity	NPC157333
0.8684	High Similarity	NPC59692
0.8684	High Similarity	NPC233467
0.8675	High Similarity	NPC477612
0.8675	High Similarity	NPC472709
0.8675	High Similarity	NPC472710
0.8671	High Similarity	NPC187194
0.8671	High Similarity	NPC476411
0.8671	High Similarity	NPC47181
0.8667	High Similarity	NPC301961
0.8667	High Similarity	NPC166584
0.8662	High Similarity	NPC207400
0.8662	High Similarity	NPC4940
0.8662	High Similarity	NPC181049
0.8658	High Similarity	NPC212890
0.8658	High Similarity	NPC260397
0.8654	High Similarity	NPC1253
0.8654	High Similarity	NPC100936
0.8652	High Similarity	NPC64201
0.8652	High Similarity	NPC173308
0.8652	High Similarity	NPC187998
0.8652	High Similarity	NPC42300
0.8652	High Similarity	NPC242807
0.8652	High Similarity	NPC145305
0.8652	High Similarity	NPC153739
0.8652	High Similarity	NPC92164
0.8652	High Similarity	NPC275950
0.8652	High Similarity	NPC257582
0.8652	High Similarity	NPC77040
0.8652	High Similarity	NPC181079
0.8652	High Similarity	NPC241522
0.8652	High Similarity	NPC174495
0.8649	High Similarity	NPC473045
0.8649	High Similarity	NPC25292
0.8643	High Similarity	NPC184733
0.8643	High Similarity	NPC165128
0.8643	High Similarity	NPC45774
0.8643	High Similarity	NPC282703
0.8643	High Similarity	NPC11258
0.8643	High Similarity	NPC21867
0.8643	High Similarity	NPC158471
0.8643	High Similarity	NPC57119
0.8643	High Similarity	NPC129570
0.8643	High Similarity	NPC226862
0.8643	High Similarity	NPC128208
0.8639	High Similarity	NPC5262
0.8639	High Similarity	NPC477800
0.8639	High Similarity	NPC477799
0.8639	High Similarity	NPC189115
0.8639	High Similarity	NPC469559
0.8639	High Similarity	NPC477794
0.8639	High Similarity	NPC472714
0.863	High Similarity	NPC226547
0.8627	High Similarity	NPC61604
0.8627	High Similarity	NPC245615
0.8627	High Similarity	NPC299706
0.8627	High Similarity	NPC115466
0.8621	High Similarity	NPC304152
0.8621	High Similarity	NPC474390
0.8621	High Similarity	NPC477797
0.8621	High Similarity	NPC477798
0.8621	High Similarity	NPC474039
0.8618	High Similarity	NPC143480

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 NPC226153 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	336
0.1-0.2	824
0.2-0.3	1728
0.3-0.4	2792
0.4-0.5	1809
0.5-0.6	1054
0.6-0.7	513
0.7-0.8	93
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8125	Intermediate Similarity	NPD6234	Discontinued
0.811	Intermediate Similarity	NPD7228	Approved
0.8079	Intermediate Similarity	NPD6674	Discontinued
0.8069	Intermediate Similarity	NPD3027	Phase 3
0.8	Intermediate Similarity	NPD4967	Phase 2
0.8	Intermediate Similarity	NPD4966	Approved
0.8	Intermediate Similarity	NPD4965	Approved
0.7947	Intermediate Similarity	NPD7266	Discontinued
0.7914	Intermediate Similarity	NPD7199	Phase 2
0.7905	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7905	Intermediate Similarity	NPD1613	Approved
0.7887	Intermediate Similarity	NPD3705	Approved
0.7871	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7812	Intermediate Similarity	NPD37	Approved
0.7764	Intermediate Similarity	NPD8455	Phase 2
0.7711	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7687	Intermediate Similarity	NPD2861	Phase 2
0.7676	Intermediate Similarity	NPD1357	Approved
0.7667	Intermediate Similarity	NPD3620	Phase 2
0.7667	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7635	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7635	Intermediate Similarity	NPD4908	Phase 1
0.763	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7602	Intermediate Similarity	NPD7240	Approved
0.7588	Intermediate Similarity	NPD7074	Phase 3
0.7574	Intermediate Similarity	NPD3818	Discontinued
0.7568	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7562	Intermediate Similarity	NPD1653	Approved
0.7533	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7529	Intermediate Similarity	NPD7054	Approved
0.75	Intermediate Similarity	NPD7685	Pre-registration
0.75	Intermediate Similarity	NPD5283	Phase 1
0.75	Intermediate Similarity	NPD5735	Approved
0.7485	Intermediate Similarity	NPD7472	Approved
0.7485	Intermediate Similarity	NPD8127	Discontinued
0.7468	Intermediate Similarity	NPD5058	Phase 3
0.7439	Intermediate Similarity	NPD2977	Approved
0.7439	Intermediate Similarity	NPD2978	Approved
0.7429	Intermediate Similarity	NPD7843	Approved
0.7403	Intermediate Similarity	NPD7097	Phase 1
0.7401	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7397	Intermediate Similarity	NPD1091	Approved
0.7394	Intermediate Similarity	NPD7157	Approved
0.7391	Intermediate Similarity	NPD7680	Approved
0.7357	Intermediate Similarity	NPD228	Approved
0.7356	Intermediate Similarity	NPD7808	Phase 3
0.7353	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7353	Intermediate Similarity	NPD6166	Phase 2
0.7353	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7349	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.732	Intermediate Similarity	NPD4060	Phase 1
0.7314	Intermediate Similarity	NPD8312	Approved
0.7314	Intermediate Similarity	NPD8313	Approved
0.7299	Intermediate Similarity	NPD7251	Discontinued
0.7273	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7268	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7261	Intermediate Similarity	NPD1375	Discontinued
0.7248	Intermediate Similarity	NPD8651	Approved
0.7241	Intermediate Similarity	NPD6797	Phase 2
0.7241	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7237	Intermediate Similarity	NPD7095	Approved
0.7214	Intermediate Similarity	NPD3021	Approved
0.7214	Intermediate Similarity	NPD3022	Approved
0.7208	Intermediate Similarity	NPD1558	Phase 1
0.7181	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7178	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7169	Intermediate Similarity	NPD1934	Approved
0.7169	Intermediate Similarity	NPD7945	Clinical (unspecified phase)
0.7162	Intermediate Similarity	NPD1610	Phase 2
0.7161	Intermediate Similarity	NPD6355	Discontinued
0.7159	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD5762	Approved
0.7152	Intermediate Similarity	NPD6584	Phase 3
0.7152	Intermediate Similarity	NPD5763	Approved
0.7143	Intermediate Similarity	NPD2684	Approved
0.7143	Intermediate Similarity	NPD5846	Approved
0.7143	Intermediate Similarity	NPD6783	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6516	Phase 2
0.7134	Intermediate Similarity	NPD5588	Approved
0.7125	Intermediate Similarity	NPD6331	Phase 2
0.7125	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7125	Intermediate Similarity	NPD4110	Phase 3
0.7107	Intermediate Similarity	NPD7037	Approved
0.7102	Intermediate Similarity	NPD6559	Discontinued
0.7101	Intermediate Similarity	NPD7833	Phase 2
0.7101	Intermediate Similarity	NPD7832	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD7831	Phase 2
0.7101	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD4140	Approved
0.7081	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.7078	Intermediate Similarity	NPD6798	Discontinued
0.707	Intermediate Similarity	NPD4538	Approved
0.707	Intermediate Similarity	NPD4536	Approved
0.707	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7067	Intermediate Similarity	NPD5327	Phase 3
0.7063	Intermediate Similarity	NPD4236	Phase 3
0.7063	Intermediate Similarity	NPD4237	Approved
0.7056	Intermediate Similarity	NPD7243	Clinical (unspecified phase)
0.7056	Intermediate Similarity	NPD7906	Approved
0.7055	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7052	Intermediate Similarity	NPD2489	Approved
0.7052	Intermediate Similarity	NPD27	Approved
0.7048	Intermediate Similarity	NPD7028	Phase 2
0.7035	Intermediate Similarity	NPD3051	Approved
0.7032	Intermediate Similarity	NPD6233	Phase 2
0.7029	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7029	Intermediate Similarity	NPD5844	Phase 1
0.7027	Intermediate Similarity	NPD5126	Approved
0.7027	Intermediate Similarity	NPD5125	Phase 3
0.7024	Intermediate Similarity	NPD6818	Clinical (unspecified phase)
0.7024	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD4628	Phase 3
0.7019	Intermediate Similarity	NPD8166	Discontinued
0.7006	Intermediate Similarity	NPD6653	Approved
0.7006	Intermediate Similarity	NPD6353	Approved
0.6994	Remote Similarity	NPD2970	Approved
0.6994	Remote Similarity	NPD2969	Approved
0.6987	Remote Similarity	NPD5837	Clinical (unspecified phase)
0.6983	Remote Similarity	NPD8053	Approved
0.6983	Remote Similarity	NPD8054	Approved
0.6982	Remote Similarity	NPD6374	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD2161	Phase 2
0.6975	Remote Similarity	NPD6190	Approved
0.6968	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD3060	Approved
0.6954	Remote Similarity	NPD6583	Phase 3
0.6954	Remote Similarity	NPD2982	Phase 2
0.6954	Remote Similarity	NPD6582	Phase 2
0.6954	Remote Similarity	NPD2983	Phase 2
0.6951	Remote Similarity	NPD4160	Clinical (unspecified phase)
0.6951	Remote Similarity	NPD7446	Clinical (unspecified phase)
0.6941	Remote Similarity	NPD3882	Suspended
0.6937	Remote Similarity	NPD2029	Clinical (unspecified phase)
0.6936	Remote Similarity	NPD3787	Discontinued
0.6927	Remote Similarity	NPD7313	Approved
0.6927	Remote Similarity	NPD7311	Approved
0.6927	Remote Similarity	NPD7312	Approved
0.6927	Remote Similarity	NPD7310	Approved
0.6923	Remote Similarity	NPD5773	Approved
0.6923	Remote Similarity	NPD2801	Approved
0.6923	Remote Similarity	NPD5772	Approved
0.6918	Remote Similarity	NPD5960	Phase 3
0.6918	Remote Similarity	NPD6029	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD6671	Approved
0.6918	Remote Similarity	NPD6028	Clinical (unspecified phase)
0.6906	Remote Similarity	NPD4663	Approved
0.6892	Remote Similarity	NPD1548	Phase 1
0.6889	Remote Similarity	NPD7309	Approved
0.6887	Remote Similarity	NPD2981	Phase 2
0.6886	Remote Similarity	NPD6055	Clinical (unspecified phase)
0.6883	Remote Similarity	NPD3018	Phase 2
0.6882	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6871	Remote Similarity	NPD2677	Approved
0.6863	Remote Similarity	NPD3094	Phase 2
0.6855	Remote Similarity	NPD7119	Phase 2
0.6852	Remote Similarity	NPD4162	Approved
0.6848	Remote Similarity	NPD4123	Phase 3
0.6842	Remote Similarity	NPD4749	Approved
0.6842	Remote Similarity	NPD3685	Discontinued
0.6842	Remote Similarity	NPD7768	Phase 2
0.6842	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD5752	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD3657	Discovery
0.6833	Remote Similarity	NPD4577	Approved
0.6833	Remote Similarity	NPD4578	Approved
0.6828	Remote Similarity	NPD5535	Approved
0.6826	Remote Similarity	NPD3687	Approved
0.6826	Remote Similarity	NPD3686	Approved
0.6826	Remote Similarity	NPD4210	Discontinued
0.6824	Remote Similarity	NPD5563	Clinical (unspecified phase)
0.6821	Remote Similarity	NPD5494	Approved
0.6821	Remote Similarity	NPD3092	Approved
0.6818	Remote Similarity	NPD7473	Discontinued
0.6815	Remote Similarity	NPD1726	Clinical (unspecified phase)
0.6813	Remote Similarity	NPD4108	Discontinued
0.681	Remote Similarity	NPD6658	Clinical (unspecified phase)
0.6807	Remote Similarity	NPD7526	Approved
0.6807	Remote Similarity	NPD6273	Approved
0.6807	Remote Similarity	NPD5261	Clinical (unspecified phase)
0.6807	Remote Similarity	NPD52	Approved
0.6807	Remote Similarity	NPD7527	Clinical (unspecified phase)
0.6797	Remote Similarity	NPD6696	Suspended
0.6795	Remote Similarity	NPD4625	Phase 3
0.6786	Remote Similarity	NPD7458	Discontinued
0.6784	Remote Similarity	NPD2560	Approved
0.6784	Remote Similarity	NPD2563	Approved
0.6784	Remote Similarity	NPD3817	Phase 2
0.6778	Remote Similarity	NPD7549	Discontinued
0.6776	Remote Similarity	NPD2231	Phase 2
0.6776	Remote Similarity	NPD2235	Phase 2
0.6776	Remote Similarity	NPD1608	Approved
0.6768	Remote Similarity	NPD5241	Discontinued
0.6761	Remote Similarity	NPD968	Approved
0.676	Remote Similarity	NPD7007	Discovery
0.6757	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6752	Remote Similarity	NPD6812	Clinical (unspecified phase)
0.6748	Remote Similarity	NPD5177	Phase 3
0.6747	Remote Similarity	NPD7447	Phase 1

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