NPASS Compound

Structure

NPC276430 OpenBabel07101719512D 50 59 0 0 1 0 0 0 0 0999 V2000 10.1673 -2.3628 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9630 -2.9029 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.1673 -3.3144 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.3431 -1.8870 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0745 -2.5618 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7025 -2.3040 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2049 -3.1327 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9966 -0.4490 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2049 -4.0843 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8478 -1.3889 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.3431 -3.7902 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.5190 -2.3628 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9257 -1.6220 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5536 -1.3641 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0290 -2.6569 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2571 0.1499 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0290 -4.5601 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9594 -1.7299 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.6949 -3.7902 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5164 -0.0832 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3175 -2.0687 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0888 1.0888 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.5190 -3.3144 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6652 -1.0231 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8531 -3.1327 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3687 -0.1912 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8531 -4.0843 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2198 -1.1311 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8708 -3.3144 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6279 0.2578 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.2225 -2.3628 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.1489 0.9399 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 6.0467 -1.8870 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5907 1.5388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0467 -3.7902 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8884 -0.3410 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3175 -3.6085 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8479 -0.4320 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.7582 -2.8386 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.5208 0.2409 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 6.8708 -2.3628 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.4791 1.1977 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 3.7582 -4.3784 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.2799 -1.2799 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 5.2225 -3.3144 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 6.0467 -0.9354 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.4418 2.4787 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.0467 -4.7418 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0373 -1.2809 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 3 2 0 0 0 0 1 4 1 0 0 0 0 2 5 2 0 0 0 0 2 6 1 0 0 0 0 3 11 1 0 0 0 0 4 12 2 0 0 0 0 5 13 1 0 0 0 0 6 14 2 0 0 0 0 7 9 2 0 0 0 0 7 15 1 0 0 0 0 8 10 2 0 0 0 0 8 16 1 0 0 0 0 9 17 1 0 0 0 0 10 18 1 0 0 0 0 11 23 2 0 0 0 0 12 23 1 0 0 0 0 13 24 2 0 0 0 0 14 24 1 0 0 0 0 15 25 2 0 0 0 0 16 26 2 0 0 0 0 17 27 2 0 0 0 0 18 28 2 0 0 0 0 19 23 1 0 0 0 0 20 24 1 0 0 0 0 25 27 1 0 0 0 0 25 39 1 0 0 0 0 26 28 1 0 0 0 0 26 40 1 0 0 0 0 27 43 1 0 0 0 0 28 44 1 0 0 0 0 29 19 1 1 0 0 0 29 35 1 0 0 0 0 29 41 1 0 0 0 0 30 20 1 6 0 0 0 30 36 1 0 0 0 0 30 42 1 0 0 0 0 31 21 1 1 0 0 0 31 33 1 0 0 0 0 31 45 1 0 0 0 0 32 22 1 6 0 0 0 32 34 1 0 0 0 0 32 46 1 0 0 0 0 33 41 2 0 0 0 0 33 47 1 0 0 0 0 34 42 2 0 0 0 0 34 48 1 0 0 0 0 35 45 1 0 0 0 0 35 49 2 0 0 0 0 36 46 1 0 0 0 0 36 50 2 0 0 0 0 37 39 1 1 0 0 0 37 43 1 0 0 0 0 37 45 1 0 0 0 0 38 40 1 6 0 0 0 38 44 1 0 0 0 0 38 46 1 0 0 0 0 39 21 1 1 0 0 0 39 40 1 0 0 0 0 40 22 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	664.28
Volume:	673.789
LogP:	4.46
LogD:	3.905
LogS:	-4.354
# Rotatable Bonds:	5
TPSA:	122.88
# H-Bond Aceptor:	10
# H-Bond Donor:	4
# Rings:	10
# Heavy Atoms:	10

MedChem Properties

QED Drug-Likeness Score:	0.26
Synthetic Accessibility Score:	4.883
Fsp3:	0.3
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.554
MDCK Permeability:	9.202954242937267e-05
Pgp-inhibitor:	0.996
Pgp-substrate:	0.944
Human Intestinal Absorption (HIA):	0.906
20% Bioavailability (F20%):	0.097
30% Bioavailability (F30%):	0.995

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.025
Plasma Protein Binding (PPB):	97.10101318359375%
Volume Distribution (VD):	0.783
Pgp-substrate:	4.275540351867676%

ADMET: Metabolism

CYP1A2-inhibitor:	0.006
CYP1A2-substrate:	0.05
CYP2C19-inhibitor:	0.883
CYP2C19-substrate:	0.09
CYP2C9-inhibitor:	0.966
CYP2C9-substrate:	0.326
CYP2D6-inhibitor:	0.04
CYP2D6-substrate:	0.132
CYP3A4-inhibitor:	0.984
CYP3A4-substrate:	0.304

ADMET: Excretion

Clearance (CL):	3.075
Half-life (T1/2):	0.131

ADMET: Toxicity

hERG Blockers:	0.093
Human Hepatotoxicity (H-HT):	0.972
Drug-inuced Liver Injury (DILI):	0.924
AMES Toxicity:	0.18
Rat Oral Acute Toxicity:	0.896
Maximum Recommended Daily Dose:	0.883
Skin Sensitization:	0.855
Carcinogencity:	0.031
Eye Corrosion:	0.003
Eye Irritation:	0.004
Respiratory Toxicity:	0.04

Download Data

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

Natural Product: NPC276430

Natural Product ID:	NPC276430
*Common Name:**	ZEANERNKMXBETI-BJHDJDSNSA-N
IUPAC Name:	n.a.
Synonyms:	WIN-64821
Standard InCHIKey:	ZEANERNKMXBETI-BJHDJDSNSA-N
Standard InCHI:	InChI=1S/C40H36N6O4/c47-33-31-21-39(25-15-7-9-17-27(25)43-37(39)45(31)35(49)29(41-33)19-23-11-3-1-4-12-23)40-22-32-34(48)42-30(20-24-13-5-2-6-14-24)36(50)46(32)38(40)44-28-18-10-8-16-26(28)40/h1-18,29-32,37-38,43-44H,19-22H2,(H,41,47)(H,42,48)/t29-,30-,31-,32-,37+,38+,39-,40-/m0/s1
SMILES:	c1ccc(cc1)C[C@H]1C(=O)N2[C@@H](C[C@@]3(c4ccccc4N[C@H]23)[C@@]23C[C@H]4C(=N[C@@H](Cc5ccccc5)C(=O)N4[C@H]3Nc3ccccc23)O)C(=N1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL504788
PubChem CID:	158365
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000211] Indoles and derivatives [CHEMONTID:0001733] Pyrroloindoles

*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
NPO23756	Aspergillus flavus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16124785]
NPO23756	Aspergillus flavus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24738739]
NPO23756	Aspergillus flavus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31050424]
NPO23756	Aspergillus flavus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[4207788]
NPO23756	Aspergillus flavus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[4629903]
NPO23756	Aspergillus flavus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7528269]
NPO23756	Aspergillus flavus	Species	Aspergillaceae	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
NPT297	Individual Protein	Neurokinin 1 receptor	Homo sapiens	IC50	=	230.0	nM	PMID[505052]

☑ 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 NPC276430 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	362
0.1-0.2	1886
0.2-0.3	13399
0.3-0.4	19069
0.4-0.5	4561
0.5-0.6	2616
0.6-0.7	749
0.7-0.8	49
0.8-0.85	4
0.85-0.9	0
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9474	High Similarity	NPC307396
0.848	Intermediate Similarity	NPC68650
0.8409	Intermediate Similarity	NPC242269
0.8158	Intermediate Similarity	NPC106118
0.8148	Intermediate Similarity	NPC471199
0.8103	Intermediate Similarity	NPC276085
0.796	Intermediate Similarity	NPC477715
0.7833	Intermediate Similarity	NPC477714
0.7817	Intermediate Similarity	NPC225400
0.7778	Intermediate Similarity	NPC472538
0.7778	Intermediate Similarity	NPC471155
0.7778	Intermediate Similarity	NPC470786
0.774	Intermediate Similarity	NPC222029
0.7739	Intermediate Similarity	NPC270241
0.7739	Intermediate Similarity	NPC471950
0.7739	Intermediate Similarity	NPC471945
0.7739	Intermediate Similarity	NPC475259
0.7716	Intermediate Similarity	NPC477179
0.77	Intermediate Similarity	NPC471951
0.77	Intermediate Similarity	NPC471946
0.7677	Intermediate Similarity	NPC254850
0.7677	Intermediate Similarity	NPC477181
0.7677	Intermediate Similarity	NPC477178
0.7677	Intermediate Similarity	NPC477180
0.765	Intermediate Similarity	NPC470491
0.765	Intermediate Similarity	NPC355
0.7644	Intermediate Similarity	NPC128582
0.7638	Intermediate Similarity	NPC477174
0.7638	Intermediate Similarity	NPC477173
0.7638	Intermediate Similarity	NPC470490
0.76	Intermediate Similarity	NPC470488
0.7598	Intermediate Similarity	NPC473003
0.7574	Intermediate Similarity	NPC191817
0.7574	Intermediate Similarity	NPC475359
0.7542	Intermediate Similarity	NPC104345
0.7487	Intermediate Similarity	NPC471436
0.745	Intermediate Similarity	NPC295548
0.7404	Intermediate Similarity	NPC248601
0.7394	Intermediate Similarity	NPC473001
0.7351	Intermediate Similarity	NPC469904
0.7318	Intermediate Similarity	NPC473002
0.7308	Intermediate Similarity	NPC469902
0.7287	Intermediate Similarity	NPC475097
0.7263	Intermediate Similarity	NPC66936
0.7258	Intermediate Similarity	NPC475248
0.7258	Intermediate Similarity	NPC63047
0.7241	Intermediate Similarity	NPC470489
0.7234	Intermediate Similarity	NPC285622
0.722	Intermediate Similarity	NPC71238
0.7182	Intermediate Similarity	NPC469903
0.7171	Intermediate Similarity	NPC54420
0.7143	Intermediate Similarity	NPC473743
0.7136	Intermediate Similarity	NPC285192
0.7136	Intermediate Similarity	NPC474896
0.7135	Intermediate Similarity	NPC91179
0.7135	Intermediate Similarity	NPC286994
0.7115	Intermediate Similarity	NPC54981
0.7114	Intermediate Similarity	NPC171317
0.7109	Intermediate Similarity	NPC471197
0.7103	Intermediate Similarity	NPC31097
0.7101	Intermediate Similarity	NPC162860
0.7089	Intermediate Similarity	NPC272174
0.7077	Intermediate Similarity	NPC259626
0.7075	Intermediate Similarity	NPC471198
0.7048	Intermediate Similarity	NPC471663
0.7032	Intermediate Similarity	NPC475859
0.7032	Intermediate Similarity	NPC475969
0.7026	Intermediate Similarity	NPC2933
0.7019	Intermediate Similarity	NPC107077
0.7019	Intermediate Similarity	NPC223791
0.7015	Intermediate Similarity	NPC470787
0.7015	Intermediate Similarity	NPC472539
0.7015	Intermediate Similarity	NPC472540
0.7014	Intermediate Similarity	NPC478157
0.7005	Intermediate Similarity	NPC17059
0.7	Intermediate Similarity	NPC75634
0.699	Remote Similarity	NPC473376
0.6989	Remote Similarity	NPC309531
0.6989	Remote Similarity	NPC472102
0.6986	Remote Similarity	NPC470730
0.6986	Remote Similarity	NPC477175
0.698	Remote Similarity	NPC472541
0.698	Remote Similarity	NPC472542
0.6974	Remote Similarity	NPC256288
0.697	Remote Similarity	NPC213629
0.6961	Remote Similarity	NPC109787
0.6959	Remote Similarity	NPC200589
0.6955	Remote Similarity	NPC474877
0.6941	Remote Similarity	NPC145754
0.6938	Remote Similarity	NPC478158
0.6935	Remote Similarity	NPC471122
0.6923	Remote Similarity	NPC165743
0.6919	Remote Similarity	NPC229484
0.6909	Remote Similarity	NPC470729
0.6909	Remote Similarity	NPC477176
0.6909	Remote Similarity	NPC69843
0.6908	Remote Similarity	NPC329833
0.6906	Remote Similarity	NPC254798
0.6901	Remote Similarity	NPC470731
0.6897	Remote Similarity	NPC162440
0.6892	Remote Similarity	NPC63279
0.6884	Remote Similarity	NPC292675
0.6882	Remote Similarity	NPC469898
0.6878	Remote Similarity	NPC471124
0.6878	Remote Similarity	NPC477177
0.6875	Remote Similarity	NPC471191
0.6872	Remote Similarity	NPC72956
0.6869	Remote Similarity	NPC473615
0.6864	Remote Similarity	NPC191382
0.6864	Remote Similarity	NPC56109
0.6861	Remote Similarity	NPC297642
0.6861	Remote Similarity	NPC325976
0.684	Remote Similarity	NPC75726
0.684	Remote Similarity	NPC31385
0.684	Remote Similarity	NPC6865
0.684	Remote Similarity	NPC153980
0.684	Remote Similarity	NPC110602
0.684	Remote Similarity	NPC471193
0.684	Remote Similarity	NPC471194
0.6828	Remote Similarity	NPC324850
0.6822	Remote Similarity	NPC470732
0.6821	Remote Similarity	NPC255447
0.6802	Remote Similarity	NPC111428
0.6791	Remote Similarity	NPC244425
0.6791	Remote Similarity	NPC15384
0.6784	Remote Similarity	NPC94752
0.6772	Remote Similarity	NPC472117
0.6757	Remote Similarity	NPC326363
0.6756	Remote Similarity	NPC478028
0.6754	Remote Similarity	NPC279527
0.6754	Remote Similarity	NPC214960
0.6744	Remote Similarity	NPC471192
0.6729	Remote Similarity	NPC54744
0.6727	Remote Similarity	NPC19170
0.6723	Remote Similarity	NPC471123
0.6716	Remote Similarity	NPC321708
0.6714	Remote Similarity	NPC320968
0.6712	Remote Similarity	NPC312942
0.6712	Remote Similarity	NPC297862
0.6712	Remote Similarity	NPC327095
0.6705	Remote Similarity	NPC473322
0.6701	Remote Similarity	NPC39822
0.6699	Remote Similarity	NPC473640
0.6696	Remote Similarity	NPC478029
0.6684	Remote Similarity	NPC14849
0.6684	Remote Similarity	NPC469741
0.6683	Remote Similarity	NPC228835
0.6683	Remote Similarity	NPC475506
0.6682	Remote Similarity	NPC40455
0.6667	Remote Similarity	NPC328611
0.6667	Remote Similarity	NPC100321
0.6667	Remote Similarity	NPC293917
0.6652	Remote Similarity	NPC28945
0.6651	Remote Similarity	NPC155143
0.665	Remote Similarity	NPC473763
0.665	Remote Similarity	NPC131450
0.665	Remote Similarity	NPC147298
0.665	Remote Similarity	NPC117244
0.665	Remote Similarity	NPC182057
0.6649	Remote Similarity	NPC189116
0.6636	Remote Similarity	NPC155444
0.6633	Remote Similarity	NPC469900
0.6632	Remote Similarity	NPC473000
0.6624	Remote Similarity	NPC14812
0.6615	Remote Similarity	NPC473880
0.6615	Remote Similarity	NPC472106
0.6613	Remote Similarity	NPC206592
0.6599	Remote Similarity	NPC59269
0.6597	Remote Similarity	NPC282339
0.6597	Remote Similarity	NPC472120
0.6597	Remote Similarity	NPC472101
0.6597	Remote Similarity	NPC99632
0.6582	Remote Similarity	NPC248862
0.6582	Remote Similarity	NPC470548
0.658	Remote Similarity	NPC141957
0.6579	Remote Similarity	NPC36495
0.6579	Remote Similarity	NPC469901
0.6579	Remote Similarity	NPC154478
0.6578	Remote Similarity	NPC117032
0.6566	Remote Similarity	NPC11126
0.6561	Remote Similarity	NPC84317
0.6556	Remote Similarity	NPC469560
0.6545	Remote Similarity	NPC225319
0.6543	Remote Similarity	NPC295021
0.6541	Remote Similarity	NPC469740
0.6532	Remote Similarity	NPC476817
0.653	Remote Similarity	NPC281049
0.6528	Remote Similarity	NPC475420
0.6526	Remote Similarity	NPC123241
0.652	Remote Similarity	NPC471196
0.652	Remote Similarity	NPC471195
0.6517	Remote Similarity	NPC472294
0.6515	Remote Similarity	NPC15573
0.6515	Remote Similarity	NPC217372
0.6515	Remote Similarity	NPC183662
0.6513	Remote Similarity	NPC472118
0.6512	Remote Similarity	NPC475422
0.651	Remote Similarity	NPC286871
0.651	Remote Similarity	NPC476231
0.651	Remote Similarity	NPC133470

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 NPC276430 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	191
0.1-0.2	476
0.2-0.3	906
0.3-0.4	1765
0.4-0.5	3535
0.5-0.6	2012
0.6-0.7	256
0.7-0.8	8
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
1.0	High Similarity	NPD8240	Discontinued
0.7444	Intermediate Similarity	NPD8630	Approved
0.7255	Intermediate Similarity	NPD8493	Clinical (unspecified phase)
0.7171	Intermediate Similarity	NPD8322	Phase 2
0.7159	Intermediate Similarity	NPD5024	Approved
0.7158	Intermediate Similarity	NPD8022	Clinical (unspecified phase)
0.7092	Intermediate Similarity	NPD8103	Clinical (unspecified phase)
0.7077	Intermediate Similarity	NPD6557	Phase 2
0.7027	Intermediate Similarity	NPD7599	Phase 2
0.6995	Remote Similarity	NPD7771	Discontinued
0.6989	Remote Similarity	NPD7600	Phase 2
0.6959	Remote Similarity	NPD3989	Phase 3
0.6949	Remote Similarity	NPD3625	Discontinued
0.6923	Remote Similarity	NPD3990	Phase 3
0.6919	Remote Similarity	NPD7594	Clinical (unspecified phase)
0.6881	Remote Similarity	NPD7944	Discontinued
0.6872	Remote Similarity	NPD8464	Clinical (unspecified phase)
0.6868	Remote Similarity	NPD4432	Discontinued
0.6868	Remote Similarity	NPD5942	Approved
0.6868	Remote Similarity	NPD5941	Approved
0.6864	Remote Similarity	NPD7781	Approved
0.6864	Remote Similarity	NPD7780	Approved
0.6836	Remote Similarity	NPD7728	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD7308	Discontinued
0.6825	Remote Similarity	NPD7998	Clinical (unspecified phase)
0.6816	Remote Similarity	NPD7791	Approved
0.6816	Remote Similarity	NPD7790	Approved
0.6816	Remote Similarity	NPD7953	Approved
0.6816	Remote Similarity	NPD7789	Approved
0.6816	Remote Similarity	NPD7951	Approved
0.6816	Remote Similarity	NPD7952	Approved
0.6816	Remote Similarity	NPD7950	Approved
0.6772	Remote Similarity	NPD5551	Clinical (unspecified phase)
0.6758	Remote Similarity	NPD8290	Clinical (unspecified phase)
0.6753	Remote Similarity	NPD7662	Clinical (unspecified phase)
0.6745	Remote Similarity	NPD7809	Clinical (unspecified phase)
0.6718	Remote Similarity	NPD4091	Approved
0.6714	Remote Similarity	NPD8013	Clinical (unspecified phase)
0.6703	Remote Similarity	NPD7785	Clinical (unspecified phase)
0.6701	Remote Similarity	NPD6879	Phase 2
0.6701	Remote Similarity	NPD6878	Phase 2
0.6685	Remote Similarity	NPD979	Approved
0.6684	Remote Similarity	NPD3992	Approved
0.6684	Remote Similarity	NPD3996	Approved
0.6684	Remote Similarity	NPD3995	Approved
0.6684	Remote Similarity	NPD3994	Approved
0.6684	Remote Similarity	NPD7587	Clinical (unspecified phase)
0.6684	Remote Similarity	NPD4092	Approved
0.6684	Remote Similarity	NPD3991	Approved
0.6684	Remote Similarity	NPD3993	Approved
0.6682	Remote Similarity	NPD8405	Clinical (unspecified phase)
0.6682	Remote Similarity	NPD7824	Approved
0.6667	Remote Similarity	NPD7621	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD8114	Approved
0.6667	Remote Similarity	NPD7979	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD3522	Approved
0.6667	Remote Similarity	NPD8115	Approved
0.6651	Remote Similarity	NPD8094	Discontinued
0.665	Remote Similarity	NPD3998	Approved
0.665	Remote Similarity	NPD3997	Approved
0.665	Remote Similarity	NPD3999	Approved
0.6649	Remote Similarity	NPD7105	Phase 1
0.6649	Remote Similarity	NPD5748	Phase 2
0.6649	Remote Similarity	NPD3790	Phase 2
0.6647	Remote Similarity	NPD5339	Clinical (unspecified phase)
0.662	Remote Similarity	NPD7971	Clinical (unspecified phase)
0.662	Remote Similarity	NPD7970	Approved
0.6618	Remote Similarity	NPD5856	Discontinued
0.661	Remote Similarity	NPD4791	Clinical (unspecified phase)
0.6605	Remote Similarity	NPD8458	Clinical (unspecified phase)
0.6605	Remote Similarity	NPD8093	Discontinued
0.6603	Remote Similarity	NPD7903	Clinical (unspecified phase)
0.6602	Remote Similarity	NPD6449	Clinical (unspecified phase)
0.6601	Remote Similarity	NPD7617	Discontinued
0.6593	Remote Similarity	NPD6301	Phase 2
0.6592	Remote Similarity	NPD7731	Approved
0.6592	Remote Similarity	NPD7730	Approved
0.6584	Remote Similarity	NPD6141	Clinical (unspecified phase)
0.6584	Remote Similarity	NPD7210	Clinical (unspecified phase)
0.6578	Remote Similarity	NPD3248	Phase 1
0.6576	Remote Similarity	NPD5839	Clinical (unspecified phase)
0.6574	Remote Similarity	NPD7557	Clinical (unspecified phase)
0.6574	Remote Similarity	NPD8488	Clinical (unspecified phase)
0.6571	Remote Similarity	NPD6359	Clinical (unspecified phase)
0.6561	Remote Similarity	NPD7091	Discontinued
0.6561	Remote Similarity	NPD951	Approved
0.656	Remote Similarity	NPD8406	Clinical (unspecified phase)
0.6558	Remote Similarity	NPD7470	Discontinued
0.6553	Remote Similarity	NPD7619	Phase 3
0.6553	Remote Similarity	NPD7618	Phase 3
0.6543	Remote Similarity	NPD7774	Clinical (unspecified phase)
0.6537	Remote Similarity	NPD7570	Approved
0.6537	Remote Similarity	NPD7569	Approved
0.6532	Remote Similarity	NPD7717	Approved
0.6532	Remote Similarity	NPD7716	Approved
0.6522	Remote Similarity	NPD7602	Clinical (unspecified phase)
0.6515	Remote Similarity	NPD8362	Clinical (unspecified phase)
0.6502	Remote Similarity	NPD7271	Approved
0.6489	Remote Similarity	NPD8400	Approved
0.6489	Remote Similarity	NPD8402	Approved
0.6489	Remote Similarity	NPD8401	Approved
0.6489	Remote Similarity	NPD6707	Clinical (unspecified phase)
0.6488	Remote Similarity	NPD5042	Phase 1
0.6484	Remote Similarity	NPD7720	Phase 2
0.6484	Remote Similarity	NPD8000	Clinical (unspecified phase)
0.6482	Remote Similarity	NPD6368	Clinical (unspecified phase)
0.6445	Remote Similarity	NPD7817	Phase 1
0.6444	Remote Similarity	NPD4782	Clinical (unspecified phase)
0.6444	Remote Similarity	NPD8125	Discontinued
0.644	Remote Similarity	NPD5715	Clinical (unspecified phase)
0.644	Remote Similarity	NPD7735	Clinical (unspecified phase)
0.6437	Remote Similarity	NPD1036	Approved
0.6432	Remote Similarity	NPD2887	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD7795	Phase 2
0.6429	Remote Similarity	NPD7968	Clinical (unspecified phase)
0.6425	Remote Similarity	NPD4565	Clinical (unspecified phase)
0.6425	Remote Similarity	NPD4564	Clinical (unspecified phase)
0.6422	Remote Similarity	NPD8431	Approved
0.6421	Remote Similarity	NPD7072	Phase 2
0.6417	Remote Similarity	NPD4682	Phase 2
0.6409	Remote Similarity	NPD8256	Approved
0.6409	Remote Similarity	NPD4077	Clinical (unspecified phase)
0.6409	Remote Similarity	NPD8257	Approved
0.6409	Remote Similarity	NPD6358	Phase 2
0.6409	Remote Similarity	NPD8258	Clinical (unspecified phase)
0.6404	Remote Similarity	NPD5581	Approved
0.64	Remote Similarity	NPD8386	Phase 2
0.639	Remote Similarity	NPD6965	Clinical (unspecified phase)
0.6387	Remote Similarity	NPD6855	Clinical (unspecified phase)
0.6386	Remote Similarity	NPD5728	Clinical (unspecified phase)
0.6373	Remote Similarity	NPD5989	Phase 1
0.6372	Remote Similarity	NPD6838	Clinical (unspecified phase)
0.6368	Remote Similarity	NPD6595	Phase 3
0.6368	Remote Similarity	NPD7014	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD8149	Discontinued
0.6364	Remote Similarity	NPD7593	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD7543	Phase 2
0.6359	Remote Similarity	NPD5341	Clinical (unspecified phase)
0.6355	Remote Similarity	NPD8272	Phase 2
0.6355	Remote Similarity	NPD5426	Phase 3
0.6343	Remote Similarity	NPD5578	Approved
0.6343	Remote Similarity	NPD8128	Discontinued
0.6343	Remote Similarity	NPD5577	Clinical (unspecified phase)
0.6339	Remote Similarity	NPD6606	Clinical (unspecified phase)
0.6328	Remote Similarity	NPD3040	Approved
0.6326	Remote Similarity	NPD7957	Phase 1
0.6326	Remote Similarity	NPD7958	Clinical (unspecified phase)
0.6321	Remote Similarity	NPD4860	Clinical (unspecified phase)
0.6318	Remote Similarity	NPD5775	Approved
0.6318	Remote Similarity	NPD5774	Approved
0.6318	Remote Similarity	NPD8112	Clinical (unspecified phase)
0.6313	Remote Similarity	NPD3632	Clinical (unspecified phase)
0.6311	Remote Similarity	NPD7855	Clinical (unspecified phase)
0.6305	Remote Similarity	NPD2095	Phase 2
0.6305	Remote Similarity	NPD2092	Phase 2
0.6305	Remote Similarity	NPD2094	Phase 2
0.6302	Remote Similarity	NPD1663	Discontinued
0.6298	Remote Similarity	NPD7786	Discontinued
0.6298	Remote Similarity	NPD3908	Approved
0.6296	Remote Similarity	NPD6328	Clinical (unspecified phase)
0.6292	Remote Similarity	NPD5263	Approved
0.6292	Remote Similarity	NPD8263	Discontinued
0.6291	Remote Similarity	NPD7727	Phase 2
0.629	Remote Similarity	NPD6506	Clinical (unspecified phase)
0.6287	Remote Similarity	NPD6833	Clinical (unspecified phase)
0.6284	Remote Similarity	NPD7825	Clinical (unspecified phase)
0.6281	Remote Similarity	NPD7854	Phase 2
0.6281	Remote Similarity	NPD750	Phase 2
0.6275	Remote Similarity	NPD2091	Phase 2
0.6275	Remote Similarity	NPD2096	Phase 2
0.6275	Remote Similarity	NPD7483	Phase 2
0.6275	Remote Similarity	NPD7482	Phase 2
0.6269	Remote Similarity	NPD6203	Clinical (unspecified phase)
0.6269	Remote Similarity	NPD5840	Discontinued
0.6269	Remote Similarity	NPD8006	Clinical (unspecified phase)
0.6267	Remote Similarity	NPD7665	Phase 2
0.6267	Remote Similarity	NPD7666	Phase 3
0.6264	Remote Similarity	NPD4761	Approved
0.6264	Remote Similarity	NPD4762	Approved
0.6263	Remote Similarity	NPD5982	Phase 2
0.6263	Remote Similarity	NPD6575	Clinical (unspecified phase)
0.6262	Remote Similarity	NPD3961	Discontinued
0.6257	Remote Similarity	NPD8323	Discontinued
0.6256	Remote Similarity	NPD7711	Discontinued
0.625	Remote Similarity	NPD482	Approved
0.625	Remote Similarity	NPD6613	Clinical (unspecified phase)
0.6244	Remote Similarity	NPD6610	Clinical (unspecified phase)
0.6243	Remote Similarity	NPD4939	Clinical (unspecified phase)
0.6243	Remote Similarity	NPD7200	Approved
0.6243	Remote Similarity	NPD5423	Phase 2
0.6237	Remote Similarity	NPD4393	Approved
0.6237	Remote Similarity	NPD33	Approved
0.6232	Remote Similarity	NPD7175	Phase 1
0.623	Remote Similarity	NPD6295	Approved
0.623	Remote Similarity	NPD3864	Clinical (unspecified phase)
0.623	Remote Similarity	NPD6901	Phase 3
0.623	Remote Similarity	NPD8315	Phase 1
0.623	Remote Similarity	NPD6294	Approved
0.6229	Remote Similarity	NPD3071	Approved
0.6229	Remote Similarity	NPD3072	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