NPASS Compound

Structure

NPC51314 OpenBabel07101719192D 60 66 0 0 1 0 0 0 0 0999 V2000 2.2888 -0.5350 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9562 -1.9923 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3274 -3.2113 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5275 -1.0753 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4135 -0.1272 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1742 0.9738 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6417 -2.5663 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0368 4.4495 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0815 2.0077 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3472 0.4964 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1742 1.9287 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2928 -1.6774 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0463 -3.3128 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0368 3.4946 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2099 4.9269 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2940 1.0767 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1690 2.2891 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5203 0.9738 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3472 2.4061 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3486 -1.5351 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1021 -3.1705 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2099 3.0172 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3830 4.4495 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5940 0.4273 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4690 1.6396 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4619 0.6300 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6852 -0.9179 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4619 -0.0576 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.0040 -1.9209 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2399 -2.9298 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5203 1.9287 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7533 -2.2817 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3830 3.4946 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6815 0.7087 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8664 0.9738 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.1845 -1.5340 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.5718 -0.9658 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.2709 0.6300 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.7524 -1.3494 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.3691 -0.3088 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6934 2.4061 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8091 -2.1393 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5560 3.0172 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9816 0.0592 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6495 -0.7000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2709 -0.0576 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8664 -0.4014 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.4661 -2.7099 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.9399 -3.5793 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6934 3.3610 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.2137 -2.8859 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.2709 3.4946 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.1940 -0.8717 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5896 -1.0606 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4524 -1.9989 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8664 1.9287 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4602 -1.2505 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5560 1.1074 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0691 0.3407 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 28 1 0 0 0 0 2 29 1 0 0 0 0 3 30 1 0 0 0 0 4 45 1 0 0 0 0 5 45 1 0 0 0 0 6 10 2 0 0 0 0 6 11 1 0 0 0 0 7 12 2 0 0 0 0 7 13 1 0 0 0 0 8 14 2 0 0 0 0 8 15 1 0 0 0 0 9 16 2 0 0 0 0 9 17 1 0 0 0 0 10 18 1 0 0 0 0 11 19 2 0 0 0 0 12 20 1 0 0 0 0 13 21 2 0 0 0 0 14 22 1 0 0 0 0 15 23 2 0 0 0 0 16 24 1 0 0 0 0 17 25 2 0 0 0 0 18 31 2 0 0 0 0 19 31 1 0 0 0 0 20 32 2 0 0 0 0 21 32 1 0 0 0 0 22 33 2 0 0 0 0 23 33 1 0 0 0 0 24 34 2 0 0 0 0 25 34 1 0 0 0 0 26 28 1 0 0 0 0 26 35 1 0 0 0 0 27 46 1 0 0 0 0 27 54 1 0 0 0 0 28 47 1 1 0 0 0 29 48 2 0 0 0 0 29 54 1 0 0 0 0 30 49 2 0 0 0 0 30 55 1 0 0 0 0 31 41 1 0 0 0 0 32 42 1 0 0 0 0 33 43 1 0 0 0 0 34 44 1 0 0 0 0 35 38 1 0 0 0 0 35 56 1 1 0 0 0 36 37 1 0 0 0 0 36 39 1 0 0 0 0 36 45 1 6 0 0 0 37 40 1 0 0 0 0 37 57 1 1 0 0 0 38 46 1 1 0 0 0 38 58 1 0 0 0 0 39 47 1 6 0 0 0 39 55 1 0 0 0 0 40 46 1 1 0 0 0 40 59 1 0 0 0 0 41 50 2 0 0 0 0 41 56 1 0 0 0 0 42 51 2 0 0 0 0 42 57 1 0 0 0 0 43 52 2 0 0 0 0 43 58 1 0 0 0 0 44 53 2 0 0 0 0 44 59 1 0 0 0 0 45 60 1 0 0 0 0 46 47 1 6 0 0 0 47 60 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	578.16
Volume:	534.737
LogP:	-0.127
LogD:	0.269
LogS:	-4.451
# Rotatable Bonds:	7
TPSA:	217.97
# H-Bond Aceptor:	14
# H-Bond Donor:	7
# Rings:	5
# Heavy Atoms:	14

MedChem Properties

QED Drug-Likeness Score:	0.176
Synthetic Accessibility Score:	4.531
Fsp3:	0.444
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:	-6.423
MDCK Permeability:	2.4968818252091296e-05
Pgp-inhibitor:	0.013
Pgp-substrate:	0.996
Human Intestinal Absorption (HIA):	0.871
20% Bioavailability (F20%):	0.004
30% Bioavailability (F30%):	0.996

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.117
Plasma Protein Binding (PPB):	79.96940612792969%
Volume Distribution (VD):	0.639
Pgp-substrate:	11.657575607299805%

ADMET: Metabolism

CYP1A2-inhibitor:	0.063
CYP1A2-substrate:	0.111
CYP2C19-inhibitor:	0.079
CYP2C19-substrate:	0.063
CYP2C9-inhibitor:	0.009
CYP2C9-substrate:	0.104
CYP2D6-inhibitor:	0.196
CYP2D6-substrate:	0.262
CYP3A4-inhibitor:	0.033
CYP3A4-substrate:	0.015

ADMET: Excretion

Clearance (CL):	1.22
Half-life (T1/2):	0.519

ADMET: Toxicity

hERG Blockers:	0.531
Human Hepatotoxicity (H-HT):	0.097
Drug-inuced Liver Injury (DILI):	0.712
AMES Toxicity:	0.537
Rat Oral Acute Toxicity:	0.049
Maximum Recommended Daily Dose:	0.013
Skin Sensitization:	0.919
Carcinogencity:	0.496
Eye Corrosion:	0.003
Eye Irritation:	0.082
Respiratory Toxicity:	0.035

Download Data

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

Natural Product: NPC51314

Natural Product ID:	NPC51314
*Common Name:**	DKUCORZJNCHLSI-BQLPCOOZSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	DKUCORZJNCHLSI-BQLPCOOZSA-N
Standard InCHI:	InChI=1S/C47H46O13/c1-28-26-35(56-41(50)31-18-10-6-11-19-31)38(58-43(52)33-22-14-8-15-23-33)46(27-54-29(2)48)40(59-44(53)34-24-16-9-17-25-34)37(57-42(51)32-20-12-7-13-21-32)36-39(55-30(3)49)47(28,46)60-45(36,4)5/h6-25,28,35-40H,26-27H2,1-5H3/t28-,35+,36-,37-,38+,39-,40-,46+,47-/m1/s1
SMILES:	CC(=O)OC[C@]12[C@@H](OC(=O)c3ccccc3)[C@@H](OC(=O)c3ccccc3)C[C@H]([C@@]32OC([C@H]([C@H]([C@H]1OC(=O)c1ccccc1)OC(=O)c1ccccc1)[C@H]3OC(=O)C)(C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL412596
PubChem CID:	44429329
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000264] Organic acids and derivatives [CHEMONTID:0000265] Carboxylic acids and derivatives [CHEMONTID:0002967] Hexacarboxylic acids and derivatives

*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
NPO25272	Celastrus angulatus	Species	Celastraceae	Eukaryota	n.a.	seed	n.a.	DOI[10.1016/S0031-9422(99)00216-2]
NPO25272	Celastrus angulatus	Species	Celastraceae	Eukaryota	seeds and root bark	Henan, China	n.a.	PMID[26295746]
NPO25272	Celastrus angulatus	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO25272	Celastrus angulatus	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25272	Celastrus angulatus	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO25272	Celastrus angulatus	Species	Celastraceae	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
Ki	2
Others	8

Activity Type	# Activity
Cell Line	2
Individual Protein	3
Others	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT519	Cell Line	SH-SY5Y	Homo sapiens	Activity	=	78.7	%	PMID[493769]
NPT80	Cell Line	Raji	Homo sapiens	Activity	=	60.0	%	PMID[493770]
NPT668	Individual Protein	P-glycoprotein 1	Homo sapiens	Ki	=	1980.0	nM	PMID[493768]
NPT35	Others	n.a.		LogP	=	12.4	n.a.	PMID[493768]
NPT668	Individual Protein	P-glycoprotein 1	Homo sapiens	Ki	=	1995.26	nM	PMID[493768]
NPT668	Individual Protein	P-glycoprotein 1	Homo sapiens	Imax	=	29.3	%	PMID[493768]
NPT2	Others	Unspecified		Activity	=	39.8	%	PMID[493770]
NPT2	Others	Unspecified		Activity	=	11.5	%	PMID[493770]
NPT2	Others	Unspecified		Activity	=	81.3	%	PMID[493770]
NPT2	Others	Unspecified		Activity	=	100.0	%	PMID[493770]

☑ 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 NPC51314 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	365
0.1-0.2	1251
0.2-0.3	2318
0.3-0.4	4878
0.4-0.5	9888
0.5-0.6	12737
0.6-0.7	9640
0.7-0.8	1231
0.8-0.85	188
0.85-0.9	56
0.9-0.95	101
0.95-1	44

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC67777
0.9926	High Similarity	NPC475429
0.9926	High Similarity	NPC147217
0.9926	High Similarity	NPC473673
0.9926	High Similarity	NPC139067
0.9926	High Similarity	NPC177340
0.9926	High Similarity	NPC191082
0.9926	High Similarity	NPC246480
0.9926	High Similarity	NPC270498
0.9704	High Similarity	NPC476094
0.9704	High Similarity	NPC43241
0.9704	High Similarity	NPC473085
0.9704	High Similarity	NPC473758
0.9704	High Similarity	NPC184747
0.9704	High Similarity	NPC473112
0.9704	High Similarity	NPC147880
0.9704	High Similarity	NPC48017
0.9704	High Similarity	NPC473613
0.9704	High Similarity	NPC473109
0.9704	High Similarity	NPC211137
0.9704	High Similarity	NPC473060
0.9704	High Similarity	NPC473081
0.9704	High Similarity	NPC4341
0.9704	High Similarity	NPC200592
0.964	High Similarity	NPC281717
0.963	High Similarity	NPC475652
0.963	High Similarity	NPC214550
0.963	High Similarity	NPC210591
0.9571	High Similarity	NPC301556
0.9571	High Similarity	NPC270590
0.9571	High Similarity	NPC92293
0.9571	High Similarity	NPC471101
0.9571	High Similarity	NPC266265
0.9556	High Similarity	NPC283375
0.9556	High Similarity	NPC183122
0.9424	High Similarity	NPC95265
0.9424	High Similarity	NPC470231
0.9424	High Similarity	NPC25768
0.9424	High Similarity	NPC188865
0.9424	High Similarity	NPC70716
0.9424	High Similarity	NPC57628
0.9424	High Similarity	NPC125106
0.9424	High Similarity	NPC472573
0.9424	High Similarity	NPC163719
0.9424	High Similarity	NPC472569
0.9424	High Similarity	NPC472570
0.9424	High Similarity	NPC11685
0.9424	High Similarity	NPC476974
0.9424	High Similarity	NPC95810
0.9407	High Similarity	NPC291638
0.9407	High Similarity	NPC66761
0.9407	High Similarity	NPC195647
0.9407	High Similarity	NPC472577
0.9407	High Similarity	NPC17877
0.9357	High Similarity	NPC177940
0.9357	High Similarity	NPC96903
0.9357	High Similarity	NPC184817
0.9357	High Similarity	NPC472568
0.9357	High Similarity	NPC200471
0.9357	High Similarity	NPC470157
0.9357	High Similarity	NPC470159
0.9357	High Similarity	NPC469349
0.9357	High Similarity	NPC471104
0.9357	High Similarity	NPC473088
0.9357	High Similarity	NPC472575
0.9357	High Similarity	NPC476973
0.9357	High Similarity	NPC158663
0.9357	High Similarity	NPC472571
0.9357	High Similarity	NPC174982
0.9357	High Similarity	NPC472572
0.9357	High Similarity	NPC171525
0.9357	High Similarity	NPC70403
0.9357	High Similarity	NPC29704
0.9353	High Similarity	NPC163087
0.9333	High Similarity	NPC474608
0.9286	High Similarity	NPC475122
0.9286	High Similarity	NPC475759
0.9286	High Similarity	NPC241951
0.9286	High Similarity	NPC470152
0.9209	High Similarity	NPC16912
0.9161	High Similarity	NPC476975
0.9155	High Similarity	NPC474935
0.9137	High Similarity	NPC171207
0.9137	High Similarity	NPC90614
0.9137	High Similarity	NPC97667
0.9097	High Similarity	NPC470245
0.9097	High Similarity	NPC473214
0.9097	High Similarity	NPC254558
0.9085	High Similarity	NPC472556
0.9071	High Similarity	NPC87448
0.9071	High Similarity	NPC118080
0.9071	High Similarity	NPC291599
0.9071	High Similarity	NPC27377
0.9071	High Similarity	NPC41481
0.9071	High Similarity	NPC97947
0.9071	High Similarity	NPC472576
0.9054	High Similarity	NPC471102
0.9037	High Similarity	NPC147561
0.9034	High Similarity	NPC470153
0.9028	High Similarity	NPC473215
0.9	High Similarity	NPC275592
0.9	High Similarity	NPC183270
0.9	High Similarity	NPC100913
0.9	High Similarity	NPC477904
0.8973	High Similarity	NPC477905
0.8966	High Similarity	NPC31829
0.8936	High Similarity	NPC224491
0.8929	High Similarity	NPC472371
0.8929	High Similarity	NPC472395
0.8857	High Similarity	NPC475373
0.8851	High Similarity	NPC26033
0.8851	High Similarity	NPC228204
0.8851	High Similarity	NPC282239
0.8844	High Similarity	NPC472548
0.8819	High Similarity	NPC471107
0.8819	High Similarity	NPC471100
0.8808	High Similarity	NPC476077
0.8792	High Similarity	NPC106895
0.8784	High Similarity	NPC237549
0.8784	High Similarity	NPC472022
0.8784	High Similarity	NPC77719
0.8784	High Similarity	NPC265395
0.8784	High Similarity	NPC249471
0.8784	High Similarity	NPC257213
0.8784	High Similarity	NPC1173
0.8784	High Similarity	NPC242262
0.8784	High Similarity	NPC304876
0.8784	High Similarity	NPC158333
0.8784	High Similarity	NPC473414
0.8784	High Similarity	NPC472005
0.8784	High Similarity	NPC256142
0.8784	High Similarity	NPC472030
0.8759	High Similarity	NPC209592
0.8759	High Similarity	NPC473602
0.8759	High Similarity	NPC48599
0.8741	High Similarity	NPC473111
0.8741	High Similarity	NPC473110
0.8741	High Similarity	NPC34012
0.8741	High Similarity	NPC473082
0.8733	High Similarity	NPC472393
0.8732	High Similarity	NPC472547
0.8725	High Similarity	NPC472549
0.8725	High Similarity	NPC114410
0.8725	High Similarity	NPC112523
0.8699	High Similarity	NPC473760
0.8681	High Similarity	NPC91703
0.8671	High Similarity	NPC266374
0.8667	High Similarity	NPC114927
0.8667	High Similarity	NPC217091
0.8667	High Similarity	NPC473083
0.8652	High Similarity	NPC472551
0.8652	High Similarity	NPC472545
0.8649	High Similarity	NPC51602
0.8611	High Similarity	NPC472546
0.8609	High Similarity	NPC469771
0.8601	High Similarity	NPC475400
0.86	High Similarity	NPC34066
0.8592	High Similarity	NPC39549
0.8582	High Similarity	NPC473216
0.8582	High Similarity	NPC473399
0.8581	High Similarity	NPC7095
0.8581	High Similarity	NPC112216
0.8581	High Similarity	NPC469448
0.8571	High Similarity	NPC472437
0.8552	High Similarity	NPC477468
0.8552	High Similarity	NPC477894
0.8523	High Similarity	NPC471103
0.8514	High Similarity	NPC76103
0.8514	High Similarity	NPC60509
0.8514	High Similarity	NPC250046
0.8514	High Similarity	NPC81698
0.8511	High Similarity	NPC48929
0.8506	High Similarity	NPC472574
0.8503	High Similarity	NPC240115
0.85	High Similarity	NPC472394
0.85	High Similarity	NPC238370
0.8497	Intermediate Similarity	NPC477623
0.8493	Intermediate Similarity	NPC34943
0.8493	Intermediate Similarity	NPC38696
0.8477	Intermediate Similarity	NPC473611
0.8477	Intermediate Similarity	NPC469422
0.8462	Intermediate Similarity	NPC30171
0.8456	Intermediate Similarity	NPC165260
0.8456	Intermediate Similarity	NPC161239
0.8456	Intermediate Similarity	NPC198455
0.8444	Intermediate Similarity	NPC70973
0.8435	Intermediate Similarity	NPC125882
0.8435	Intermediate Similarity	NPC127857
0.8431	Intermediate Similarity	NPC469399
0.8429	Intermediate Similarity	NPC472361
0.8425	Intermediate Similarity	NPC131966
0.8425	Intermediate Similarity	NPC191387
0.8421	Intermediate Similarity	NPC323001
0.8421	Intermediate Similarity	NPC326235
0.8411	Intermediate Similarity	NPC472658
0.8411	Intermediate Similarity	NPC472657
0.8406	Intermediate Similarity	NPC473220
0.8406	Intermediate Similarity	NPC470753
0.84	Intermediate Similarity	NPC96308
0.8392	Intermediate Similarity	NPC472374

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 NPC51314 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	294
0.1-0.2	764
0.2-0.3	1343
0.3-0.4	2870
0.4-0.5	2390
0.5-0.6	1179
0.6-0.7	287
0.7-0.8	23
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
0.7724	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7712	Intermediate Similarity	NPD7236	Approved
0.759	Intermediate Similarity	NPD7799	Discontinued
0.758	Intermediate Similarity	NPD7239	Suspended
0.7545	Intermediate Similarity	NPD8470	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD7008	Discontinued
0.7399	Intermediate Similarity	NPD8434	Phase 2
0.7384	Intermediate Similarity	NPD8407	Phase 2
0.736	Intermediate Similarity	NPD8485	Approved
0.7355	Intermediate Similarity	NPD8166	Discontinued
0.7314	Intermediate Similarity	NPD8360	Approved
0.7314	Intermediate Similarity	NPD8435	Approved
0.7314	Intermediate Similarity	NPD8361	Approved
0.731	Intermediate Similarity	NPD8368	Discontinued
0.7299	Intermediate Similarity	NPD2181	Clinical (unspecified phase)
0.7289	Intermediate Similarity	NPD8127	Discontinued
0.7244	Intermediate Similarity	NPD7003	Approved
0.7241	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7238	Intermediate Similarity	NPD8486	Clinical (unspecified phase)
0.7225	Intermediate Similarity	NPD8312	Approved
0.7225	Intermediate Similarity	NPD8313	Approved
0.7216	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7205	Intermediate Similarity	NPD7458	Discontinued
0.72	Intermediate Similarity	NPD3764	Approved
0.72	Intermediate Similarity	NPD8424	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD7961	Discontinued
0.7152	Intermediate Similarity	NPD7058	Phase 2
0.7152	Intermediate Similarity	NPD7057	Phase 3
0.7135	Intermediate Similarity	NPD5844	Phase 1
0.7125	Intermediate Similarity	NPD6273	Approved
0.7103	Intermediate Similarity	NPD7457	Clinical (unspecified phase)
0.7102	Intermediate Similarity	NPD8150	Discontinued
0.7081	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7051	Intermediate Similarity	NPD7702	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD7768	Phase 2
0.7047	Intermediate Similarity	NPD6007	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7034	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD8455	Phase 2
0.7029	Intermediate Similarity	NPD2182	Approved
0.7025	Intermediate Similarity	NPD4628	Phase 3
0.7024	Intermediate Similarity	NPD5494	Approved
0.7014	Intermediate Similarity	NPD7741	Discontinued
0.6972	Remote Similarity	NPD5951	Approved
0.697	Remote Similarity	NPD37	Approved
0.695	Remote Similarity	NPD6858	Approved
0.695	Remote Similarity	NPD7094	Approved
0.6946	Remote Similarity	NPD4965	Approved
0.6946	Remote Similarity	NPD4967	Phase 2
0.6946	Remote Similarity	NPD4966	Approved
0.6946	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6939	Remote Similarity	NPD6287	Discontinued
0.6928	Remote Similarity	NPD7713	Phase 3
0.6928	Remote Similarity	NPD7819	Suspended
0.6923	Remote Similarity	NPD4198	Discontinued
0.6919	Remote Similarity	NPD7473	Discontinued
0.6918	Remote Similarity	NPD7163	Clinical (unspecified phase)
0.6883	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD5406	Approved
0.6879	Remote Similarity	NPD5404	Approved
0.6879	Remote Similarity	NPD5408	Approved
0.6879	Remote Similarity	NPD5405	Approved
0.6879	Remote Similarity	NPD7228	Approved
0.6875	Remote Similarity	NPD6190	Approved
0.6864	Remote Similarity	NPD6234	Discontinued
0.686	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6853	Remote Similarity	NPD2629	Approved
0.6852	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6845	Remote Similarity	NPD7497	Discontinued
0.6842	Remote Similarity	NPD6232	Discontinued
0.6815	Remote Similarity	NPD7798	Approved
0.6815	Remote Similarity	NPD3748	Approved
0.6815	Remote Similarity	NPD1238	Approved
0.6803	Remote Similarity	NPD5125	Phase 3
0.6803	Remote Similarity	NPD5126	Approved
0.6788	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6784	Remote Similarity	NPD6959	Discontinued
0.6772	Remote Similarity	NPD2438	Suspended
0.675	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6748	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6747	Remote Similarity	NPD6599	Discontinued
0.6739	Remote Similarity	NPD164	Approved
0.6726	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6723	Remote Similarity	NPD7240	Approved
0.6712	Remote Similarity	NPD7610	Discontinued
0.671	Remote Similarity	NPD8032	Phase 2
0.6708	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6707	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.6707	Remote Similarity	NPD7411	Suspended
0.6706	Remote Similarity	NPD7075	Discontinued
0.6687	Remote Similarity	NPD6591	Clinical (unspecified phase)
0.6687	Remote Similarity	NPD7390	Discontinued
0.6687	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6686	Remote Similarity	NPD5402	Approved
0.6667	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7699	Phase 2
0.6667	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7700	Phase 2
0.6647	Remote Similarity	NPD4380	Phase 2
0.6646	Remote Similarity	NPD7097	Phase 1
0.6632	Remote Similarity	NPD8320	Phase 1
0.6632	Remote Similarity	NPD8319	Approved
0.6632	Remote Similarity	NPD7870	Phase 2
0.6632	Remote Similarity	NPD7871	Phase 2
0.6629	Remote Similarity	NPD7685	Pre-registration
0.6629	Remote Similarity	NPD6559	Discontinued
0.6627	Remote Similarity	NPD5760	Phase 2
0.6627	Remote Similarity	NPD5761	Phase 2
0.6625	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6623	Remote Similarity	NPD6832	Phase 2
0.662	Remote Similarity	NPD2067	Discontinued
0.6608	Remote Similarity	NPD3749	Approved
0.6605	Remote Similarity	NPD3750	Approved
0.6603	Remote Similarity	NPD7715	Approved
0.6603	Remote Similarity	NPD6663	Approved
0.6603	Remote Similarity	NPD7714	Approved
0.6595	Remote Similarity	NPD6534	Approved
0.6595	Remote Similarity	NPD6535	Approved
0.659	Remote Similarity	NPD7199	Phase 2
0.6588	Remote Similarity	NPD3817	Phase 2
0.6587	Remote Similarity	NPD3226	Approved
0.6579	Remote Similarity	NPD7435	Discontinued
0.6571	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6571	Remote Similarity	NPD6166	Phase 2
0.6571	Remote Similarity	NPD7997	Clinical (unspecified phase)
0.6571	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6568	Remote Similarity	NPD6801	Discontinued
0.6566	Remote Similarity	NPD5403	Approved
0.6564	Remote Similarity	NPD8462	Phase 1
0.6564	Remote Similarity	NPD7274	Clinical (unspecified phase)
0.6562	Remote Similarity	NPD2935	Discontinued
0.6562	Remote Similarity	NPD2796	Approved
0.6561	Remote Similarity	NPD2979	Phase 3
0.6558	Remote Similarity	NPD5736	Approved
0.6545	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6545	Remote Similarity	NPD2533	Approved
0.6545	Remote Similarity	NPD2534	Approved
0.6545	Remote Similarity	NPD2532	Approved
0.6545	Remote Similarity	NPD5401	Approved
0.6536	Remote Similarity	NPD6764	Approved
0.6536	Remote Similarity	NPD6765	Approved
0.6528	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD7266	Discontinued
0.6522	Remote Similarity	NPD2346	Discontinued
0.6519	Remote Similarity	NPD6355	Discontinued
0.6514	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6514	Remote Similarity	NPD8051	Clinical (unspecified phase)
0.6507	Remote Similarity	NPD690	Clinical (unspecified phase)
0.6497	Remote Similarity	NPD7177	Discontinued
0.6497	Remote Similarity	NPD6233	Phase 2
0.6495	Remote Similarity	NPD8151	Discontinued
0.6492	Remote Similarity	NPD7696	Phase 3
0.6492	Remote Similarity	NPD7698	Approved
0.6492	Remote Similarity	NPD7697	Approved
0.6485	Remote Similarity	NPD6799	Approved
0.6471	Remote Similarity	NPD5667	Approved
0.6462	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6462	Remote Similarity	NPD7874	Approved
0.6461	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6457	Remote Similarity	NPD7229	Phase 3
0.6456	Remote Similarity	NPD4307	Phase 2
0.6455	Remote Similarity	NPD8285	Discontinued
0.6447	Remote Similarity	NPD3972	Approved
0.644	Remote Similarity	NPD6823	Phase 2
0.6438	Remote Similarity	NPD4869	Clinical (unspecified phase)
0.6433	Remote Similarity	NPD6798	Discontinued
0.6433	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6432	Remote Similarity	NPD8404	Phase 2
0.6429	Remote Similarity	NPD1930	Approved
0.6429	Remote Similarity	NPD1931	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD1929	Approved
0.6425	Remote Similarity	NPD7074	Phase 3
0.6421	Remote Similarity	NPD6780	Approved
0.6421	Remote Similarity	NPD6779	Approved
0.6421	Remote Similarity	NPD6776	Approved
0.6421	Remote Similarity	NPD6781	Approved
0.6421	Remote Similarity	NPD6777	Approved
0.6421	Remote Similarity	NPD6778	Approved
0.6421	Remote Similarity	NPD6782	Approved
0.6416	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6415	Remote Similarity	NPD230	Phase 1
0.6412	Remote Similarity	NPD6873	Phase 2
0.6412	Remote Similarity	NPD6385	Approved
0.6412	Remote Similarity	NPD6386	Approved
0.6404	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6404	Remote Similarity	NPD3818	Discontinued
0.6402	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6402	Remote Similarity	NPD4110	Phase 3
0.6398	Remote Similarity	NPD2799	Discontinued
0.6395	Remote Similarity	NPD8438	Clinical (unspecified phase)
0.6393	Remote Similarity	NPD6784	Approved
0.6393	Remote Similarity	NPD6785	Approved
0.6383	Remote Similarity	NPD5909	Discontinued
0.6382	Remote Similarity	NPD1281	Approved
0.6379	Remote Similarity	NPD919	Approved
0.6374	Remote Similarity	NPD1934	Approved
0.6369	Remote Similarity	NPD7095	Approved
0.6369	Remote Similarity	NPD7054	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