NPASS Compound

Structure

NPC470271 OpenBabel07101718192D 55 60 0 0 1 0 0 0 0 0999 V2000 -4.0961 1.4189 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7345 1.4189 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0961 -0.4730 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2769 0.9459 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1916 -3.4555 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0189 -1.5530 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7262 -2.7813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4086 -0.4254 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9153 0.9459 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2769 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3098 -2.8762 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4448 -1.6945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0961 2.3649 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7345 2.3649 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9153 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0961 1.4189 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6341 -3.8476 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4285 -1.9795 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8192 -0.4730 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.8707 -2.6889 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2803 -2.2625 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9153 2.8378 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9153 0.9459 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1950 -3.6604 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2640 -2.5474 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3133 -3.0810 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6899 -2.6889 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8192 -1.4189 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8192 -1.4189 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -1.8919 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.9153 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4576 -0.4730 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3265 -1.1152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8192 -0.4730 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.2769 2.8378 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.5537 2.8378 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.7345 -0.4730 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.0961 2.3649 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.4449 -4.7744 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3470 -1.7531 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.9153 3.7838 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.7345 1.4189 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.9031 -4.2877 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.9193 -3.2296 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.2106 -2.7815 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4267 -3.5975 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6384 -1.8919 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.7345 -0.4730 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.4576 -1.4189 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.1812 -0.7097 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.2535 -2.4261 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.9526 -0.6572 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 -1.6384 -1.8919 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6384 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 9 2 0 0 0 0 1 13 1 0 0 0 0 2 9 1 0 0 0 0 2 14 2 0 0 0 0 3 10 2 0 0 0 0 3 15 1 0 0 0 0 4 10 1 0 0 0 0 4 16 2 0 0 0 0 5 11 2 0 0 0 0 5 17 1 0 0 0 0 6 12 2 0 0 0 0 6 18 1 0 0 0 0 7 11 1 0 0 0 0 7 51 1 0 0 0 0 8 52 1 0 0 0 0 9 31 1 0 0 0 0 10 32 1 0 0 0 0 11 20 1 0 0 0 0 12 21 1 0 0 0 0 12 33 1 0 0 0 0 13 22 2 0 0 0 0 13 35 1 0 0 0 0 14 22 1 0 0 0 0 14 36 1 0 0 0 0 15 23 2 0 0 0 0 15 37 1 0 0 0 0 16 23 1 0 0 0 0 16 38 1 0 0 0 0 17 24 2 0 0 0 0 17 39 1 0 0 0 0 18 25 2 0 0 0 0 18 40 1 0 0 0 0 19 8 1 1 0 0 0 19 29 1 0 0 0 0 19 53 1 0 0 0 0 20 21 1 0 0 0 0 20 26 2 0 0 0 0 21 27 2 0 0 0 0 22 41 1 0 0 0 0 23 42 1 0 0 0 0 24 26 1 0 0 0 0 24 43 1 0 0 0 0 25 27 1 0 0 0 0 25 44 1 0 0 0 0 26 45 1 0 0 0 0 27 46 1 0 0 0 0 28 30 1 0 0 0 0 28 34 1 0 0 0 0 28 47 1 6 0 0 0 29 30 1 0 0 0 0 29 54 1 6 0 0 0 30 51 1 1 0 0 0 31 48 2 0 0 0 0 31 54 1 0 0 0 0 32 49 2 0 0 0 0 32 55 1 0 0 0 0 33 50 2 0 0 0 0 33 52 1 0 0 0 0 34 53 1 0 0 0 0 34 55 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	772.11
Volume:	690.329
LogP:	1.432
LogD:	0.634
LogS:	-2.91
# Rotatable Bonds:	6
TPSA:	360.35
# H-Bond Aceptor:	21
# H-Bond Donor:	13
# Rings:	6
# Heavy Atoms:	21

MedChem Properties

QED Drug-Likeness Score:	0.078
Synthetic Accessibility Score:	6.12
Fsp3:	0.206
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:	-7.061
MDCK Permeability:	4.984015504305717e-06
Pgp-inhibitor:	0.123
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.998
20% Bioavailability (F20%):	1.0
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.002
Plasma Protein Binding (PPB):	87.48815155029297%
Volume Distribution (VD):	0.406
Pgp-substrate:	24.662452697753906%

ADMET: Metabolism

CYP1A2-inhibitor:	0.148
CYP1A2-substrate:	0.01
CYP2C19-inhibitor:	0.01
CYP2C19-substrate:	0.021
CYP2C9-inhibitor:	0.381
CYP2C9-substrate:	0.018
CYP2D6-inhibitor:	0.0
CYP2D6-substrate:	0.071
CYP3A4-inhibitor:	0.011
CYP3A4-substrate:	0.002

ADMET: Excretion

Clearance (CL):	9.236
Half-life (T1/2):	0.96

ADMET: Toxicity

hERG Blockers:	0.204
Human Hepatotoxicity (H-HT):	0.249
Drug-inuced Liver Injury (DILI):	0.991
AMES Toxicity:	0.146
Rat Oral Acute Toxicity:	0.0
Maximum Recommended Daily Dose:	0.009
Skin Sensitization:	0.977
Carcinogencity:	0.011
Eye Corrosion:	0.003
Eye Irritation:	0.929
Respiratory Toxicity:	0.002

Download Data

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

Natural Product: NPC470271

Natural Product ID:	NPC470271
*Common Name:**	Tercatain
IUPAC Name:	n.a.
Synonyms:	Tercatain
Standard InCHIKey:	RHYYKHORHGKJES-FEUHLQPKSA-N
Standard InCHI:	InChI=1S/C34H28O21/c35-13-1-9(2-14(36)22(13)41)31(48)54-29-19-8-52-33(50)12-6-18(40)25(44)27(46)21(12)20-11(5-17(39)24(43)26(20)45)7-51-30(29)28(47)34(53-19)55-32(49)10-3-15(37)23(42)16(38)4-10/h1-6,19,28-30,34-47H,7-8H2/t19-,28-,29-,30-,34+/m1/s1
SMILES:	O[C@H]1[C@@H](O[C@H]2[C@H]([C@@H]1OCc1cc(O)c(c(c1c1c(C(=O)OC2)cc(c(c1O)O)O)O)O)OC(=O)c1cc(O)c(c(c1)O)O)OC(=O)c1cc(O)c(c(c1)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1939393
PubChem CID:	57395396
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000238] Tannins [CHEMONTID:0001710] Hydrolyzable tannins

*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
NPO22608	Excoecaria agallocha	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21190854]
NPO22608	Excoecaria agallocha	Species	Euphorbiaceae	Eukaryota	stems and twigs	Beihai, Guangxi province, China	2008-Jan	PMID[22196120]
NPO22608	Excoecaria agallocha	Species	Euphorbiaceae	Eukaryota	n.a.	twig	n.a.	PMID[7623051]
NPO22608	Excoecaria agallocha	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7623051]
NPO22608	Excoecaria agallocha	Species	Euphorbiaceae	Eukaryota	n.a.	bark	n.a.	PMID[7623051]
NPO22608	Excoecaria agallocha	Species	Euphorbiaceae	Eukaryota	n.a.	leaf	n.a.	PMID[7623051]
NPO22608	Excoecaria agallocha	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO22608	Excoecaria agallocha	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22608	Excoecaria agallocha	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO22608	Excoecaria agallocha	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	1

Activity Type	# Activity
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified		IC50	>	10.0	ug.mL-1	PMID[550481]

☑ 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 NPC470271 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	399
0.1-0.2	1625
0.2-0.3	3501
0.3-0.4	8056
0.4-0.5	9515
0.5-0.6	5631
0.6-0.7	6469
0.7-0.8	6216
0.8-0.85	985
0.85-0.9	225
0.9-0.95	55
0.95-1	20

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC311389
0.9936	High Similarity	NPC175793
0.9874	High Similarity	NPC470272
0.9873	High Similarity	NPC190204
0.9873	High Similarity	NPC43918
0.9873	High Similarity	NPC261411
0.975	High Similarity	NPC47521
0.9748	High Similarity	NPC31034
0.9745	High Similarity	NPC14030
0.9745	High Similarity	NPC291957
0.9684	High Similarity	NPC470898
0.9632	High Similarity	NPC472723
0.9515	High Similarity	NPC80956
0.949	High Similarity	NPC172419
0.949	High Similarity	NPC238419
0.9427	High Similarity	NPC247629
0.9427	High Similarity	NPC239019
0.9383	High Similarity	NPC217781
0.9379	High Similarity	NPC166851
0.9379	High Similarity	NPC162169
0.9345	High Similarity	NPC231254
0.9341	High Similarity	NPC8940
0.9321	High Similarity	NPC142707
0.9321	High Similarity	NPC26536
0.9321	High Similarity	NPC49983
0.9321	High Similarity	NPC317671
0.9308	High Similarity	NPC210501
0.9308	High Similarity	NPC104222
0.9308	High Similarity	NPC114791
0.9308	High Similarity	NPC141331
0.9308	High Similarity	NPC318826
0.929	High Similarity	NPC261623
0.929	High Similarity	NPC111490
0.9277	High Similarity	NPC297574
0.9245	High Similarity	NPC135222
0.9245	High Similarity	NPC474010
0.9236	High Similarity	NPC16024
0.9236	High Similarity	NPC44260
0.9236	High Similarity	NPC61152
0.9236	High Similarity	NPC205037
0.9236	High Similarity	NPC3746
0.9235	High Similarity	NPC65489
0.9181	High Similarity	NPC119094
0.9181	High Similarity	NPC173872
0.9176	High Similarity	NPC469650
0.9172	High Similarity	NPC123259
0.9172	High Similarity	NPC129533
0.9167	High Similarity	NPC198902
0.9128	High Similarity	NPC469652
0.9128	High Similarity	NPC472720
0.9128	High Similarity	NPC31208
0.9128	High Similarity	NPC472724
0.9128	High Similarity	NPC160543
0.9128	High Similarity	NPC472721
0.9128	High Similarity	NPC93065
0.9123	High Similarity	NPC260521
0.9123	High Similarity	NPC469649
0.9075	High Similarity	NPC264302
0.907	High Similarity	NPC477083
0.907	High Similarity	NPC142291
0.907	High Similarity	NPC240200
0.907	High Similarity	NPC158214
0.907	High Similarity	NPC223534
0.907	High Similarity	NPC269046
0.907	High Similarity	NPC7839
0.907	High Similarity	NPC290289
0.907	High Similarity	NPC477081
0.9017	High Similarity	NPC187632
0.9017	High Similarity	NPC201814
0.9012	High Similarity	NPC237202
0.9	High Similarity	NPC208797
0.9	High Similarity	NPC53680
0.8987	High Similarity	NPC140151
0.8981	High Similarity	NPC92117
0.8976	High Similarity	NPC198125
0.8976	High Similarity	NPC95421
0.8971	High Similarity	NPC476358
0.8966	High Similarity	NPC471091
0.8966	High Similarity	NPC97924
0.8966	High Similarity	NPC40078
0.8963	High Similarity	NPC469651
0.8935	High Similarity	NPC67629
0.8935	High Similarity	NPC79736
0.8929	High Similarity	NPC473550
0.8929	High Similarity	NPC263119
0.8929	High Similarity	NPC46640
0.8929	High Similarity	NPC166674
0.8929	High Similarity	NPC219600
0.8929	High Similarity	NPC34436
0.8922	High Similarity	NPC181778
0.8917	High Similarity	NPC120621
0.8917	High Similarity	NPC142528
0.8917	High Similarity	NPC248257
0.8916	High Similarity	NPC473818
0.8882	High Similarity	NPC267549
0.8876	High Similarity	NPC171706
0.8869	High Similarity	NPC65333
0.8864	High Similarity	NPC477082
0.8862	High Similarity	NPC149300
0.8848	High Similarity	NPC121290
0.8837	High Similarity	NPC297503
0.8837	High Similarity	NPC97119
0.8837	High Similarity	NPC135831
0.8793	High Similarity	NPC105591
0.878	High Similarity	NPC24627
0.878	High Similarity	NPC289346
0.8779	High Similarity	NPC125352
0.8773	High Similarity	NPC257309
0.8765	High Similarity	NPC203757
0.8764	High Similarity	NPC189312
0.8764	High Similarity	NPC3474
0.8757	High Similarity	NPC100251
0.8757	High Similarity	NPC47140
0.8757	High Similarity	NPC67134
0.875	High Similarity	NPC658
0.875	High Similarity	NPC197708
0.8734	High Similarity	NPC268366
0.8728	High Similarity	NPC132111
0.8726	High Similarity	NPC108455
0.8721	High Similarity	NPC471030
0.8713	High Similarity	NPC473713
0.8712	High Similarity	NPC300845
0.8712	High Similarity	NPC134925
0.8712	High Similarity	NPC104983
0.8712	High Similarity	NPC88803
0.8712	High Similarity	NPC250436
0.8712	High Similarity	NPC291948
0.8706	High Similarity	NPC175230
0.8706	High Similarity	NPC172033
0.8706	High Similarity	NPC98583
0.8706	High Similarity	NPC88560
0.8698	High Similarity	NPC204937
0.8698	High Similarity	NPC149011
0.8686	High Similarity	NPC179947
0.8675	High Similarity	NPC33298
0.8675	High Similarity	NPC4013
0.8675	High Similarity	NPC285108
0.8675	High Similarity	NPC90905
0.8671	High Similarity	NPC170203
0.8671	High Similarity	NPC469371
0.8667	High Similarity	NPC24164
0.8667	High Similarity	NPC174140
0.8663	High Similarity	NPC476619
0.8663	High Similarity	NPC258044
0.8663	High Similarity	NPC113836
0.8663	High Similarity	NPC476618
0.8663	High Similarity	NPC196127
0.8663	High Similarity	NPC476620
0.8663	High Similarity	NPC267680
0.8663	High Similarity	NPC476622
0.8663	High Similarity	NPC476621
0.8663	High Similarity	NPC293626
0.8663	High Similarity	NPC253521
0.8663	High Similarity	NPC217387
0.8663	High Similarity	NPC476623
0.8663	High Similarity	NPC37668
0.8662	High Similarity	NPC229036
0.8662	High Similarity	NPC22176
0.8662	High Similarity	NPC121573
0.8662	High Similarity	NPC226738
0.8662	High Similarity	NPC190587
0.8659	High Similarity	NPC38779
0.8659	High Similarity	NPC114179
0.8659	High Similarity	NPC68324
0.8659	High Similarity	NPC289322
0.8659	High Similarity	NPC160512
0.8659	High Similarity	NPC156818
0.8659	High Similarity	NPC472860
0.865	High Similarity	NPC472835
0.865	High Similarity	NPC172920
0.865	High Similarity	NPC156624
0.8647	High Similarity	NPC38438
0.8647	High Similarity	NPC102851
0.8647	High Similarity	NPC5786
0.8636	High Similarity	NPC473618
0.8634	High Similarity	NPC252979
0.8629	High Similarity	NPC474093
0.8629	High Similarity	NPC104910
0.8625	High Similarity	NPC75945
0.8614	High Similarity	NPC266365
0.8613	High Similarity	NPC472725
0.8613	High Similarity	NPC472726
0.8606	High Similarity	NPC87317
0.8605	High Similarity	NPC472991
0.8605	High Similarity	NPC472992
0.8605	High Similarity	NPC61904
0.8605	High Similarity	NPC144097
0.8598	High Similarity	NPC318432
0.8596	High Similarity	NPC472993
0.858	High Similarity	NPC72554
0.858	High Similarity	NPC30011
0.858	High Similarity	NPC269625
0.858	High Similarity	NPC311912
0.858	High Similarity	NPC97817
0.858	High Similarity	NPC475179
0.8571	High Similarity	NPC49690
0.8571	High Similarity	NPC318119
0.8563	High Similarity	NPC476371
0.8563	High Similarity	NPC476372
0.8562	High Similarity	NPC81835

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 NPC470271 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	350
0.1-0.2	916
0.2-0.3	1840
0.3-0.4	2776
0.4-0.5	1899
0.5-0.6	993
0.6-0.7	245
0.7-0.8	115
0.8-0.85	14
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8757	High Similarity	NPD7993	Clinical (unspecified phase)
0.8712	High Similarity	NPD4868	Clinical (unspecified phase)
0.8266	Intermediate Similarity	NPD7472	Approved
0.8266	Intermediate Similarity	NPD7074	Phase 3
0.8256	Intermediate Similarity	NPD7228	Approved
0.8256	Intermediate Similarity	NPD3818	Discontinued
0.8253	Intermediate Similarity	NPD1465	Phase 2
0.8229	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8218	Intermediate Similarity	NPD6797	Phase 2
0.8208	Intermediate Similarity	NPD5844	Phase 1
0.8208	Intermediate Similarity	NPD7054	Approved
0.8182	Intermediate Similarity	NPD8313	Approved
0.8182	Intermediate Similarity	NPD8312	Approved
0.8171	Intermediate Similarity	NPD7251	Discontinued
0.8156	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.8125	Intermediate Similarity	NPD7808	Phase 3
0.8107	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8095	Intermediate Similarity	NPD8151	Discontinued
0.8066	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.8059	Intermediate Similarity	NPD6234	Discontinued
0.8036	Intermediate Similarity	NPD8455	Phase 2
0.8035	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8035	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8035	Intermediate Similarity	NPD6166	Phase 2
0.8023	Intermediate Similarity	NPD6232	Discontinued
0.7976	Intermediate Similarity	NPD37	Approved
0.7941	Intermediate Similarity	NPD4965	Approved
0.7941	Intermediate Similarity	NPD4967	Phase 2
0.7941	Intermediate Similarity	NPD4966	Approved
0.7914	Intermediate Similarity	NPD6190	Approved
0.7911	Intermediate Similarity	NPD230	Phase 1
0.7888	Intermediate Similarity	NPD7266	Discontinued
0.7886	Intermediate Similarity	NPD7473	Discontinued
0.7865	Intermediate Similarity	NPD7240	Approved
0.7865	Intermediate Similarity	NPD7685	Pre-registration
0.7861	Intermediate Similarity	NPD7199	Phase 2
0.7861	Intermediate Similarity	NPD6959	Discontinued
0.7797	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.779	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7784	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7765	Intermediate Similarity	NPD1934	Approved
0.7765	Intermediate Similarity	NPD6559	Discontinued
0.7751	Intermediate Similarity	NPD4380	Phase 2
0.7727	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7719	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.767	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.764	Intermediate Similarity	NPD3751	Discontinued
0.7633	Intermediate Similarity	NPD1653	Approved
0.7616	Intermediate Similarity	NPD7819	Suspended
0.7614	Intermediate Similarity	NPD3787	Discontinued
0.7605	Intermediate Similarity	NPD7390	Discontinued
0.7604	Intermediate Similarity	NPD8319	Approved
0.7604	Intermediate Similarity	NPD8320	Phase 1
0.7594	Intermediate Similarity	NPD6534	Approved
0.7594	Intermediate Similarity	NPD6535	Approved
0.7586	Intermediate Similarity	NPD3749	Approved
0.7566	Intermediate Similarity	NPD7699	Phase 2
0.7566	Intermediate Similarity	NPD7700	Phase 2
0.756	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7554	Intermediate Similarity	NPD8150	Discontinued
0.7552	Intermediate Similarity	NPD7435	Discontinued
0.7529	Intermediate Similarity	NPD7768	Phase 2
0.7514	Intermediate Similarity	NPD2801	Approved
0.75	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7487	Intermediate Similarity	NPD6782	Approved
0.7487	Intermediate Similarity	NPD6778	Approved
0.7487	Intermediate Similarity	NPD6777	Approved
0.7487	Intermediate Similarity	NPD6779	Approved
0.7487	Intermediate Similarity	NPD6780	Approved
0.7487	Intermediate Similarity	NPD6776	Approved
0.7487	Intermediate Similarity	NPD6781	Approved
0.7486	Intermediate Similarity	NPD7075	Discontinued
0.7471	Intermediate Similarity	NPD3817	Phase 2
0.7462	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7462	Intermediate Similarity	NPD7783	Phase 2
0.7461	Intermediate Similarity	NPD7680	Approved
0.7435	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7429	Intermediate Similarity	NPD3882	Suspended
0.7425	Intermediate Similarity	NPD3750	Approved
0.7423	Intermediate Similarity	NPD7870	Phase 2
0.7423	Intermediate Similarity	NPD7871	Phase 2
0.7411	Intermediate Similarity	NPD7874	Approved
0.7411	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD943	Approved
0.7399	Intermediate Similarity	NPD7411	Suspended
0.7396	Intermediate Similarity	NPD1511	Approved
0.7394	Intermediate Similarity	NPD5405	Approved
0.7394	Intermediate Similarity	NPD5408	Approved
0.7394	Intermediate Similarity	NPD5406	Approved
0.7394	Intermediate Similarity	NPD5404	Approved
0.7391	Intermediate Similarity	NPD3764	Approved
0.7371	Intermediate Similarity	NPD7697	Approved
0.7371	Intermediate Similarity	NPD7696	Phase 3
0.7371	Intermediate Similarity	NPD5402	Approved
0.7371	Intermediate Similarity	NPD7698	Approved
0.7371	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7354	Intermediate Similarity	NPD6212	Phase 3
0.7354	Intermediate Similarity	NPD6213	Phase 3
0.7354	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.7325	Intermediate Similarity	NPD9269	Phase 2
0.7321	Intermediate Similarity	NPD8166	Discontinued
0.7314	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD1512	Approved
0.731	Intermediate Similarity	NPD7701	Phase 2
0.7305	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD5494	Approved
0.7283	Intermediate Similarity	NPD7458	Discontinued
0.7283	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7257	Intermediate Similarity	NPD6801	Discontinued
0.7251	Intermediate Similarity	NPD2533	Approved
0.7251	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7251	Intermediate Similarity	NPD2532	Approved
0.7251	Intermediate Similarity	NPD2534	Approved
0.7231	Intermediate Similarity	NPD6823	Phase 2
0.7229	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD4628	Phase 3
0.7202	Intermediate Similarity	NPD1549	Phase 2
0.72	Intermediate Similarity	NPD7801	Approved
0.7195	Intermediate Similarity	NPD1613	Approved
0.7195	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7168	Intermediate Similarity	NPD5403	Approved
0.7143	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7136	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD3748	Approved
0.7126	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD1510	Phase 2
0.7093	Intermediate Similarity	NPD6799	Approved
0.7074	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.707	Intermediate Similarity	NPD9268	Approved
0.7059	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7052	Intermediate Similarity	NPD5401	Approved
0.7052	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7045	Intermediate Similarity	NPD6599	Discontinued
0.7035	Intermediate Similarity	NPD7211	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD7003	Approved
0.7012	Intermediate Similarity	NPD3027	Phase 3
0.6994	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6978	Remote Similarity	NPD8127	Discontinued
0.6959	Remote Similarity	NPD6674	Discontinued
0.6954	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6951	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.694	Remote Similarity	NPD7229	Phase 3
0.6911	Remote Similarity	NPD8434	Phase 2
0.6902	Remote Similarity	NPD5242	Approved
0.6902	Remote Similarity	NPD3926	Phase 2
0.6893	Remote Similarity	NPD3226	Approved
0.6889	Remote Similarity	NPD5353	Approved
0.6886	Remote Similarity	NPD1240	Approved
0.6882	Remote Similarity	NPD2935	Discontinued
0.6882	Remote Similarity	NPD2796	Approved
0.6882	Remote Similarity	NPD7177	Discontinued
0.6881	Remote Similarity	NPD7585	Approved
0.6867	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6848	Remote Similarity	NPD5710	Approved
0.6848	Remote Similarity	NPD5711	Approved
0.6845	Remote Similarity	NPD7930	Approved
0.6832	Remote Similarity	NPD7583	Approved
0.6821	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD6273	Approved
0.6805	Remote Similarity	NPD1607	Approved
0.6802	Remote Similarity	NPD8090	Clinical (unspecified phase)
0.6798	Remote Similarity	NPD3455	Phase 2
0.6792	Remote Similarity	NPD9545	Approved
0.6784	Remote Similarity	NPD1551	Phase 2
0.6776	Remote Similarity	NPD919	Approved
0.6765	Remote Similarity	NPD4978	Clinical (unspecified phase)
0.6755	Remote Similarity	NPD8470	Clinical (unspecified phase)
0.6753	Remote Similarity	NPD4287	Approved
0.6749	Remote Similarity	NPD7584	Approved
0.6747	Remote Similarity	NPD4908	Phase 1
0.6746	Remote Similarity	NPD1933	Approved
0.6745	Remote Similarity	NPD5619	Clinical (unspecified phase)
0.6729	Remote Similarity	NPD8059	Phase 3
0.6729	Remote Similarity	NPD8058	Clinical (unspecified phase)
0.6716	Remote Similarity	NPD5006	Approved
0.6716	Remote Similarity	NPD5005	Approved
0.6707	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6703	Remote Similarity	NPD4288	Approved
0.6702	Remote Similarity	NPD7549	Discontinued
0.6702	Remote Similarity	NPD7799	Discontinued
0.67	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.67	Remote Similarity	NPD7999	Approved
0.6687	Remote Similarity	NPD9494	Approved
0.6686	Remote Similarity	NPD6099	Approved
0.6686	Remote Similarity	NPD6100	Approved
0.6667	Remote Similarity	NPD4160	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD1470	Approved
0.6667	Remote Similarity	NPD7097	Phase 1
0.6667	Remote Similarity	NPD6798	Discontinued
0.6649	Remote Similarity	NPD8368	Discontinued
0.6647	Remote Similarity	NPD447	Suspended
0.6647	Remote Similarity	NPD2029	Clinical (unspecified phase)
0.6647	Remote Similarity	NPD2346	Discontinued
0.663	Remote Similarity	NPD6386	Approved
0.663	Remote Similarity	NPD6385	Approved
0.6617	Remote Similarity	NPD8486	Clinical (unspecified phase)
0.6615	Remote Similarity	NPD6842	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