NPASS Compound

Structure

NPC254823 OpenBabel07101719252D 47 55 0 0 1 0 0 0 0 0999 V2000 -6.7593 -6.1987 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9773 -5.2907 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5293 -1.7014 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3011 0.4724 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4677 2.1660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9898 1.5742 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7069 -5.2001 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.6535 -0.0276 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3612 3.4505 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8419 -1.9412 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8419 1.0588 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7158 -2.7013 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.5499 -2.2042 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8159 -4.7461 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0036 -0.8507 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0248 -1.7502 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9758 -1.4412 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6589 -0.1322 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7734 2.6415 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.7679 2.5370 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.2467 -0.9412 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.7079 -1.4412 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.8419 0.0588 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.3120 -0.0983 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1098 0.0588 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1098 1.0588 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7636 -3.7475 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1928 -0.7899 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4370 -0.9412 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7160 1.2402 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.7079 -0.4412 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.3667 1.7280 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.9758 1.5588 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.6589 -1.7502 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.9758 -0.4412 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.6917 0.4275 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.7376 -2.9092 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.8726 -3.2935 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.4538 -1.5528 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.4370 -0.9412 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.1715 1.7009 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.9703 1.6634 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.0368 -2.5331 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0097 1.3755 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.6023 -3.2028 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.0248 -0.1322 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 7 1 0 0 0 0 2 14 1 0 0 0 0 3 15 1 0 0 0 0 6 44 1 0 0 0 0 7 14 2 0 0 0 0 8 18 1 0 0 0 0 8 21 1 0 0 0 0 9 19 1 0 0 0 0 9 20 1 0 0 0 0 10 17 1 0 0 0 0 10 22 1 0 0 0 0 11 23 1 0 0 0 0 11 33 1 0 0 0 0 12 16 1 0 0 0 0 12 37 1 0 0 0 0 13 34 1 0 0 0 0 13 45 1 0 0 0 0 14 27 1 0 0 0 0 15 24 2 0 0 0 0 15 28 1 0 0 0 0 16 17 2 0 0 0 0 16 29 1 0 0 0 0 18 21 1 0 0 0 0 18 31 1 1 0 0 0 19 20 1 0 0 0 0 19 32 1 1 0 0 0 20 33 1 1 0 0 0 21 34 1 1 0 0 0 22 31 1 1 0 0 0 22 34 1 0 0 0 0 23 31 1 6 0 0 0 23 35 1 0 0 0 0 24 25 1 0 0 0 0 24 36 1 0 0 0 0 25 26 2 0 0 0 0 25 35 1 0 0 0 0 26 32 1 0 0 0 0 26 33 1 0 0 0 0 27 38 2 0 0 0 0 27 45 1 0 0 0 0 28 39 2 0 0 0 0 28 47 1 0 0 0 0 29 40 2 0 0 0 0 29 46 1 0 0 0 0 30 32 1 1 0 0 0 30 36 1 0 0 0 0 30 41 1 0 0 0 0 31 4 1 1 0 0 0 32 5 1 1 0 0 0 33 42 1 1 0 0 0 34 43 1 1 0 0 0 35 17 1 6 0 0 0 35 46 1 0 0 0 0 36 44 1 6 0 0 0 36 47 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	650.27
Volume:	632.441
LogP:	2.821
LogD:	1.766
LogS:	-4.557
# Rotatable Bonds:	6
TPSA:	169.05
# H-Bond Aceptor:	11
# H-Bond Donor:	4
# Rings:	9
# Heavy Atoms:	11

MedChem Properties

QED Drug-Likeness Score:	0.194
Synthetic Accessibility Score:	6.941
Fsp3:	0.694
Lipinski Rule-of-5:	Rejected
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:	-5.373
MDCK Permeability:	5.937888636253774e-05
Pgp-inhibitor:	0.993
Pgp-substrate:	0.998
Human Intestinal Absorption (HIA):	0.066
20% Bioavailability (F20%):	0.998
30% Bioavailability (F30%):	0.99

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.792
Plasma Protein Binding (PPB):	53.4669189453125%
Volume Distribution (VD):	0.911
Pgp-substrate:	19.891366958618164%

ADMET: Metabolism

CYP1A2-inhibitor:	0.01
CYP1A2-substrate:	0.98
CYP2C19-inhibitor:	0.078
CYP2C19-substrate:	0.617
CYP2C9-inhibitor:	0.091
CYP2C9-substrate:	0.003
CYP2D6-inhibitor:	0.007
CYP2D6-substrate:	0.021
CYP3A4-inhibitor:	0.788
CYP3A4-substrate:	0.819

ADMET: Excretion

Clearance (CL):	3.742
Half-life (T1/2):	0.065

ADMET: Toxicity

hERG Blockers:	0.18
Human Hepatotoxicity (H-HT):	0.494
Drug-inuced Liver Injury (DILI):	0.333
AMES Toxicity:	0.487
Rat Oral Acute Toxicity:	0.083
Maximum Recommended Daily Dose:	0.955
Skin Sensitization:	0.732
Carcinogencity:	0.276
Eye Corrosion:	0.003
Eye Irritation:	0.015
Respiratory Toxicity:	0.986

Download Data

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

Natural Product: NPC254823

Natural Product ID:	NPC254823
*Common Name:**	Chloramultiol C
IUPAC Name:	n.a.
Synonyms:	Chloramultiol C
Standard InCHIKey:	QEKDFQHMYVWLIF-HYZASWLWSA-N
Standard InCHI:	InChI=1S/C36H42O11/c1-7-14(2)27(38)45-13-34(43)21-8-18(21)31(4)22(34)10-17-16(12-37)29(40)46-35(17)23(31)11-33(42)20-9-19(20)32(5)26(33)25(35)24-15(3)28(39)47-36(24,44-6)30(32)41/h7,18-23,30,37,41-43H,8-13H2,1-6H3/b14-7+/t18-,19-,20+,21+,22-,23+,30-,31+,32+,33+,34+,35+,36+/m1/s1
SMILES:	C/C=C(C)/C(=O)OC[C@@]1([C@H]2C[C@H]2[C@@]2(C)[C@H]1CC1=C(CO)C(=O)O[C@@]31[C@H]2C[C@@]1([C@H]2C[C@H]2[C@@]2(C)C1=C3C1=C(C)C(=O)O[C@@]1([C@@H]2O)OC)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1097988
PubChem CID:	46834848
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids

*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
NPO8670	Chloranthus multistachys	Species	Chloranthaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20392109]
NPO8670	Chloranthus multistachys	Species	Chloranthaceae	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	5

Activity Type	# Activity
Cell Line	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	IC50	>	10000.0	nM	PMID[497593]
NPT116	Cell Line	HL-60	Homo sapiens	IC50	>	10000.0	nM	PMID[497593]
NPT461	Cell Line	PANC-1	Homo sapiens	IC50	>	10000.0	nM	PMID[497593]
NPT659	Cell Line	SMMC-7721	Homo sapiens	IC50	>	10000.0	nM	PMID[497593]
NPT134	Cell Line	SK-BR-3	Homo sapiens	IC50	>	10000.0	nM	PMID[497593]

☑ 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 NPC254823 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	288
0.1-0.2	1676
0.2-0.3	5049
0.3-0.4	10058
0.4-0.5	12743
0.5-0.6	7955
0.6-0.7	4109
0.7-0.8	763
0.8-0.85	31
0.85-0.9	8
0.9-0.95	4
0.95-1	13

Similarity Score	Similarity Level	Natural Product ID
0.9916	High Similarity	NPC134902
0.9754	High Similarity	NPC60150
0.9754	High Similarity	NPC192334
0.9672	High Similarity	NPC476097
0.9672	High Similarity	NPC24599
0.9672	High Similarity	NPC327664
0.9672	High Similarity	NPC470427
0.959	High Similarity	NPC476824
0.958	High Similarity	NPC226049
0.9496	High Similarity	NPC84865
0.9412	High Similarity	NPC27335
0.9	High Similarity	NPC25887
0.8931	High Similarity	NPC470426
0.8779	High Similarity	NPC476825
0.8605	High Similarity	NPC469674
0.8462	Intermediate Similarity	NPC469673
0.845	Intermediate Similarity	NPC220757
0.845	Intermediate Similarity	NPC196921
0.8397	Intermediate Similarity	NPC476823
0.8385	Intermediate Similarity	NPC34963
0.8372	Intermediate Similarity	NPC35109
0.8321	Intermediate Similarity	NPC58029
0.8308	Intermediate Similarity	NPC241935
0.8308	Intermediate Similarity	NPC279478
0.8226	Intermediate Similarity	NPC203862
0.8145	Intermediate Similarity	NPC470075
0.814	Intermediate Similarity	NPC15095
0.8095	Intermediate Similarity	NPC304260
0.8095	Intermediate Similarity	NPC29639
0.8095	Intermediate Similarity	NPC5883
0.8095	Intermediate Similarity	NPC44899
0.808	Intermediate Similarity	NPC93883
0.8065	Intermediate Similarity	NPC106446
0.8047	Intermediate Similarity	NPC115349
0.8031	Intermediate Similarity	NPC107607
0.8016	Intermediate Similarity	NPC218093
0.8015	Intermediate Similarity	NPC311534
0.8	Intermediate Similarity	NPC63186
0.8	Intermediate Similarity	NPC310341
0.8	Intermediate Similarity	NPC99620
0.8	Intermediate Similarity	NPC5311
0.8	Intermediate Similarity	NPC193382
0.8	Intermediate Similarity	NPC199428
0.7983	Intermediate Similarity	NPC85742
0.7969	Intermediate Similarity	NPC475219
0.7969	Intermediate Similarity	NPC231518
0.7969	Intermediate Similarity	NPC40749
0.7953	Intermediate Similarity	NPC469756
0.7953	Intermediate Similarity	NPC55532
0.7953	Intermediate Similarity	NPC32177
0.7953	Intermediate Similarity	NPC153085
0.7953	Intermediate Similarity	NPC236973
0.7953	Intermediate Similarity	NPC268326
0.7953	Intermediate Similarity	NPC292467
0.7953	Intermediate Similarity	NPC81222
0.7953	Intermediate Similarity	NPC470897
0.7953	Intermediate Similarity	NPC30483
0.7953	Intermediate Similarity	NPC291820
0.7939	Intermediate Similarity	NPC42399
0.7937	Intermediate Similarity	NPC27507
0.7937	Intermediate Similarity	NPC243196
0.7937	Intermediate Similarity	NPC471353
0.7937	Intermediate Similarity	NPC77319
0.7937	Intermediate Similarity	NPC309034
0.7937	Intermediate Similarity	NPC84987
0.7937	Intermediate Similarity	NPC152615
0.7937	Intermediate Similarity	NPC244402
0.7937	Intermediate Similarity	NPC157376
0.7937	Intermediate Similarity	NPC87250
0.7937	Intermediate Similarity	NPC290693
0.7937	Intermediate Similarity	NPC99728
0.7937	Intermediate Similarity	NPC34390
0.7937	Intermediate Similarity	NPC158344
0.7937	Intermediate Similarity	NPC471355
0.7937	Intermediate Similarity	NPC471354
0.7937	Intermediate Similarity	NPC471351
0.7937	Intermediate Similarity	NPC50305
0.7937	Intermediate Similarity	NPC142066
0.7937	Intermediate Similarity	NPC473852
0.7937	Intermediate Similarity	NPC196429
0.7937	Intermediate Similarity	NPC474418
0.792	Intermediate Similarity	NPC69576
0.792	Intermediate Similarity	NPC31354
0.792	Intermediate Similarity	NPC84949
0.792	Intermediate Similarity	NPC471633
0.7917	Intermediate Similarity	NPC161775
0.7907	Intermediate Similarity	NPC471082
0.7907	Intermediate Similarity	NPC193893
0.7903	Intermediate Similarity	NPC328074
0.7903	Intermediate Similarity	NPC321272
0.7903	Intermediate Similarity	NPC470025
0.7903	Intermediate Similarity	NPC317460
0.7891	Intermediate Similarity	NPC475629
0.7891	Intermediate Similarity	NPC475556
0.7891	Intermediate Similarity	NPC72260
0.7886	Intermediate Similarity	NPC177047
0.7874	Intermediate Similarity	NPC83287
0.7846	Intermediate Similarity	NPC129992
0.784	Intermediate Similarity	NPC470027
0.7836	Intermediate Similarity	NPC231240
0.7829	Intermediate Similarity	NPC475590
0.7829	Intermediate Similarity	NPC233500
0.7829	Intermediate Similarity	NPC120390
0.7829	Intermediate Similarity	NPC474908
0.7829	Intermediate Similarity	NPC46570
0.7829	Intermediate Similarity	NPC173555
0.7829	Intermediate Similarity	NPC314535
0.7829	Intermediate Similarity	NPC475419
0.7823	Intermediate Similarity	NPC470076
0.7823	Intermediate Similarity	NPC17791
0.782	Intermediate Similarity	NPC473593
0.7812	Intermediate Similarity	NPC329905
0.7812	Intermediate Similarity	NPC219656
0.7805	Intermediate Similarity	NPC257853
0.7803	Intermediate Similarity	NPC146456
0.7803	Intermediate Similarity	NPC469757
0.7803	Intermediate Similarity	NPC471357
0.7803	Intermediate Similarity	NPC117702
0.7803	Intermediate Similarity	NPC287423
0.7787	Intermediate Similarity	NPC472820
0.7786	Intermediate Similarity	NPC8374
0.7778	Intermediate Similarity	NPC216665
0.7778	Intermediate Similarity	NPC316915
0.7778	Intermediate Similarity	NPC43213
0.7769	Intermediate Similarity	NPC473543
0.7769	Intermediate Similarity	NPC264336
0.7769	Intermediate Similarity	NPC196130
0.7769	Intermediate Similarity	NPC23786
0.7769	Intermediate Similarity	NPC107493
0.7769	Intermediate Similarity	NPC470265
0.7769	Intermediate Similarity	NPC74259
0.7769	Intermediate Similarity	NPC474423
0.7761	Intermediate Similarity	NPC173347
0.7752	Intermediate Similarity	NPC475136
0.7752	Intermediate Similarity	NPC474466
0.7752	Intermediate Similarity	NPC470312
0.7752	Intermediate Similarity	NPC17938
0.7744	Intermediate Similarity	NPC245094
0.7744	Intermediate Similarity	NPC473888
0.7742	Intermediate Similarity	NPC316708
0.773	Intermediate Similarity	NPC471172
0.7727	Intermediate Similarity	NPC179261
0.7724	Intermediate Similarity	NPC470024
0.7721	Intermediate Similarity	NPC471234
0.7717	Intermediate Similarity	NPC207637
0.7714	Intermediate Similarity	NPC5153
0.7714	Intermediate Similarity	NPC48414
0.771	Intermediate Similarity	NPC219804
0.771	Intermediate Similarity	NPC308262
0.771	Intermediate Similarity	NPC208193
0.771	Intermediate Similarity	NPC117445
0.771	Intermediate Similarity	NPC27363
0.7705	Intermediate Similarity	NPC119855
0.7705	Intermediate Similarity	NPC220217
0.7705	Intermediate Similarity	NPC85670
0.7705	Intermediate Similarity	NPC472818
0.7698	Intermediate Similarity	NPC264153
0.7692	Intermediate Similarity	NPC476204
0.7692	Intermediate Similarity	NPC202051
0.7692	Intermediate Similarity	NPC170084
0.7692	Intermediate Similarity	NPC129434
0.7692	Intermediate Similarity	NPC67569
0.7687	Intermediate Similarity	NPC469755
0.7687	Intermediate Similarity	NPC469752
0.7687	Intermediate Similarity	NPC471407
0.7687	Intermediate Similarity	NPC104382
0.7687	Intermediate Similarity	NPC471361
0.7687	Intermediate Similarity	NPC86159
0.7687	Intermediate Similarity	NPC469754
0.7687	Intermediate Similarity	NPC284406
0.7687	Intermediate Similarity	NPC251866
0.7687	Intermediate Similarity	NPC89514
0.7687	Intermediate Similarity	NPC9499
0.7687	Intermediate Similarity	NPC180079
0.7687	Intermediate Similarity	NPC10823
0.7687	Intermediate Similarity	NPC6108
0.7687	Intermediate Similarity	NPC476966
0.7687	Intermediate Similarity	NPC219085
0.7687	Intermediate Similarity	NPC471352
0.7687	Intermediate Similarity	NPC17896
0.7687	Intermediate Similarity	NPC197707
0.7687	Intermediate Similarity	NPC70542
0.7687	Intermediate Similarity	NPC471360
0.7687	Intermediate Similarity	NPC231529
0.7687	Intermediate Similarity	NPC469753
0.7687	Intermediate Similarity	NPC469751
0.7687	Intermediate Similarity	NPC471359
0.7687	Intermediate Similarity	NPC471358
0.7686	Intermediate Similarity	NPC474124
0.7686	Intermediate Similarity	NPC472821
0.7686	Intermediate Similarity	NPC473523
0.768	Intermediate Similarity	NPC284162
0.768	Intermediate Similarity	NPC255401
0.768	Intermediate Similarity	NPC470026
0.768	Intermediate Similarity	NPC471484
0.768	Intermediate Similarity	NPC262083
0.7674	Intermediate Similarity	NPC278681
0.7669	Intermediate Similarity	NPC298841
0.7669	Intermediate Similarity	NPC329784
0.7669	Intermediate Similarity	NPC240070

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 NPC254823 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	244
0.1-0.2	1816
0.2-0.3	4064
0.3-0.4	2092
0.4-0.5	558
0.5-0.6	278
0.6-0.7	78
0.7-0.8	20
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
0.7969	Intermediate Similarity	NPD8033	Approved
0.7891	Intermediate Similarity	NPD8377	Approved
0.7891	Intermediate Similarity	NPD8294	Approved
0.7874	Intermediate Similarity	NPD7328	Approved
0.7874	Intermediate Similarity	NPD7327	Approved
0.7829	Intermediate Similarity	NPD8378	Approved
0.7829	Intermediate Similarity	NPD7503	Approved
0.7829	Intermediate Similarity	NPD8379	Approved
0.7829	Intermediate Similarity	NPD8296	Approved
0.7829	Intermediate Similarity	NPD8335	Approved
0.7829	Intermediate Similarity	NPD8380	Approved
0.7812	Intermediate Similarity	NPD7516	Approved
0.7687	Intermediate Similarity	NPD7319	Approved
0.7594	Intermediate Similarity	NPD7507	Approved
0.7407	Intermediate Similarity	NPD7078	Approved
0.7385	Intermediate Similarity	NPD7115	Discovery
0.7259	Intermediate Similarity	NPD7492	Approved
0.7226	Intermediate Similarity	NPD7736	Approved
0.7218	Intermediate Similarity	NPD6054	Approved
0.7206	Intermediate Similarity	NPD6616	Approved
0.7165	Intermediate Similarity	NPD6686	Approved
0.7154	Intermediate Similarity	NPD7640	Approved
0.7154	Intermediate Similarity	NPD7639	Approved
0.7153	Intermediate Similarity	NPD8293	Discontinued
0.7111	Intermediate Similarity	NPD6370	Approved
0.709	Intermediate Similarity	NPD6059	Approved
0.709	Intermediate Similarity	NPD6319	Approved
0.7073	Intermediate Similarity	NPD4225	Approved
0.7073	Intermediate Similarity	NPD7638	Approved
0.7037	Intermediate Similarity	NPD6015	Approved
0.7037	Intermediate Similarity	NPD6016	Approved
0.6985	Remote Similarity	NPD5988	Approved
0.6977	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.696	Remote Similarity	NPD5344	Discontinued
0.6947	Remote Similarity	NPD8297	Approved
0.6947	Remote Similarity	NPD6882	Approved
0.6923	Remote Similarity	NPD6371	Approved
0.6912	Remote Similarity	NPD8515	Approved
0.6912	Remote Similarity	NPD8517	Approved
0.6912	Remote Similarity	NPD8516	Approved
0.6912	Remote Similarity	NPD8513	Phase 3
0.688	Remote Similarity	NPD6648	Approved
0.6866	Remote Similarity	NPD6009	Approved
0.6822	Remote Similarity	NPD6412	Phase 2
0.6818	Remote Similarity	NPD6053	Discontinued
0.68	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6794	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6777	Remote Similarity	NPD7838	Discovery
0.6769	Remote Similarity	NPD7320	Approved
0.6767	Remote Similarity	NPD8133	Approved
0.6767	Remote Similarity	NPD4632	Approved
0.6692	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6691	Remote Similarity	NPD7604	Phase 2
0.6667	Remote Similarity	NPD8074	Phase 3
0.6645	Remote Similarity	NPD7625	Phase 1
0.6641	Remote Similarity	NPD6899	Approved
0.6641	Remote Similarity	NPD6881	Approved
0.6641	Remote Similarity	NPD7632	Discontinued
0.662	Remote Similarity	NPD6033	Approved
0.6617	Remote Similarity	NPD6649	Approved
0.6617	Remote Similarity	NPD6650	Approved
0.6617	Remote Similarity	NPD8130	Phase 1
0.6615	Remote Similarity	NPD6008	Approved
0.6615	Remote Similarity	NPD6675	Approved
0.6615	Remote Similarity	NPD7128	Approved
0.6615	Remote Similarity	NPD6402	Approved
0.6615	Remote Similarity	NPD5739	Approved
0.6591	Remote Similarity	NPD6372	Approved
0.6591	Remote Similarity	NPD6373	Approved
0.6585	Remote Similarity	NPD7637	Suspended
0.6571	Remote Similarity	NPD8328	Phase 3
0.6565	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6565	Remote Similarity	NPD5697	Approved
0.6541	Remote Similarity	NPD4634	Approved
0.6541	Remote Similarity	NPD7102	Approved
0.6541	Remote Similarity	NPD7290	Approved
0.6541	Remote Similarity	NPD6883	Approved
0.6493	Remote Similarity	NPD6617	Approved
0.6493	Remote Similarity	NPD6847	Approved
0.6493	Remote Similarity	NPD6869	Approved
0.6466	Remote Similarity	NPD6013	Approved
0.6466	Remote Similarity	NPD6012	Approved
0.6466	Remote Similarity	NPD6014	Approved
0.6466	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6439	Remote Similarity	NPD5701	Approved
0.6429	Remote Similarity	NPD5983	Phase 2
0.6393	Remote Similarity	NPD7524	Approved
0.6391	Remote Similarity	NPD6011	Approved
0.6385	Remote Similarity	NPD5211	Phase 2
0.6377	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD6336	Discontinued
0.6338	Remote Similarity	NPD6067	Discontinued
0.6331	Remote Similarity	NPD7799	Discontinued
0.6328	Remote Similarity	NPD6084	Phase 2
0.6328	Remote Similarity	NPD6083	Phase 2
0.6301	Remote Similarity	NPD5956	Approved
0.6299	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6299	Remote Similarity	NPD5695	Phase 3
0.629	Remote Similarity	NPD6051	Approved
0.6288	Remote Similarity	NPD5141	Approved
0.6281	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.627	Remote Similarity	NPD5779	Approved
0.627	Remote Similarity	NPD5778	Approved
0.6259	Remote Similarity	NPD7260	Phase 2
0.625	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.625	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.624	Remote Similarity	NPD6698	Approved
0.624	Remote Similarity	NPD46	Approved
0.6231	Remote Similarity	NPD4696	Approved
0.6231	Remote Similarity	NPD5285	Approved
0.6231	Remote Similarity	NPD5286	Approved
0.622	Remote Similarity	NPD6001	Approved
0.6202	Remote Similarity	NPD4755	Approved
0.6198	Remote Similarity	NPD6695	Phase 3
0.619	Remote Similarity	NPD5284	Approved
0.619	Remote Similarity	NPD7983	Approved
0.619	Remote Similarity	NPD5281	Approved
0.6187	Remote Similarity	NPD6274	Approved
0.617	Remote Similarity	NPD7100	Approved
0.617	Remote Similarity	NPD7101	Approved
0.6148	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6148	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6142	Remote Similarity	NPD6399	Phase 3
0.6142	Remote Similarity	NPD4202	Approved
0.6136	Remote Similarity	NPD5224	Approved
0.6136	Remote Similarity	NPD5226	Approved
0.6136	Remote Similarity	NPD4633	Approved
0.6136	Remote Similarity	NPD5225	Approved
0.6129	Remote Similarity	NPD7750	Discontinued
0.6129	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6111	Remote Similarity	NPD5785	Approved
0.6107	Remote Similarity	NPD4700	Approved
0.6107	Remote Similarity	NPD6845	Suspended
0.6099	Remote Similarity	NPD6335	Approved
0.609	Remote Similarity	NPD5175	Approved
0.609	Remote Similarity	NPD5174	Approved
0.608	Remote Similarity	NPD6903	Approved
0.6063	Remote Similarity	NPD6411	Approved
0.6063	Remote Similarity	NPD6050	Approved
0.6061	Remote Similarity	NPD4159	Approved
0.6061	Remote Similarity	NPD5223	Approved
0.6031	Remote Similarity	NPD5696	Approved
0.6029	Remote Similarity	NPD4729	Approved
0.6029	Remote Similarity	NPD4730	Approved
0.6028	Remote Similarity	NPD6317	Approved
0.6	Remote Similarity	NPD7829	Approved
0.6	Remote Similarity	NPD4767	Approved
0.6	Remote Similarity	NPD4768	Approved
0.6	Remote Similarity	NPD7830	Approved
0.5986	Remote Similarity	NPD6314	Approved
0.5986	Remote Similarity	NPD6313	Approved
0.5984	Remote Similarity	NPD5207	Approved
0.5984	Remote Similarity	NPD5692	Phase 3
0.5972	Remote Similarity	NPD6908	Approved
0.5972	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.5972	Remote Similarity	NPD6909	Approved
0.5969	Remote Similarity	NPD7748	Approved
0.5968	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.5954	Remote Similarity	NPD7902	Approved
0.595	Remote Similarity	NPD6931	Approved
0.595	Remote Similarity	NPD6930	Phase 2
0.595	Remote Similarity	NPD7525	Registered
0.5948	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.5946	Remote Similarity	NPD8336	Approved
0.5946	Remote Similarity	NPD8337	Approved
0.5942	Remote Similarity	NPD5248	Approved
0.5942	Remote Similarity	NPD5250	Approved
0.5942	Remote Similarity	NPD5249	Phase 3
0.5942	Remote Similarity	NPD5251	Approved
0.5942	Remote Similarity	NPD5247	Approved
0.5938	Remote Similarity	NPD5694	Approved
0.5938	Remote Similarity	NPD6079	Approved
0.5938	Remote Similarity	NPD5693	Phase 1
0.592	Remote Similarity	NPD7334	Approved
0.592	Remote Similarity	NPD5330	Approved
0.592	Remote Similarity	NPD6409	Approved
0.592	Remote Similarity	NPD7146	Approved
0.592	Remote Similarity	NPD6684	Approved
0.592	Remote Similarity	NPD7521	Approved
0.5912	Remote Similarity	NPD5128	Approved
0.5909	Remote Similarity	NPD6334	Approved
0.5909	Remote Similarity	NPD6333	Approved
0.5906	Remote Similarity	NPD6101	Approved
0.5906	Remote Similarity	NPD5328	Approved
0.5906	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.5906	Remote Similarity	NPD4753	Phase 2
0.5902	Remote Similarity	NPD6902	Approved
0.5894	Remote Similarity	NPD8338	Approved
0.5894	Remote Similarity	NPD8449	Approved
0.5891	Remote Similarity	NPD8171	Discontinued
0.5873	Remote Similarity	NPD4251	Approved
0.5873	Remote Similarity	NPD4250	Approved
0.5868	Remote Similarity	NPD6929	Approved
0.5855	Remote Similarity	NPD8450	Suspended
0.5852	Remote Similarity	NPD4754	Approved
0.5839	Remote Similarity	NPD7236	Approved
0.5833	Remote Similarity	NPD5959	Approved
0.5833	Remote Similarity	NPD4522	Approved
0.5827	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.582	Remote Similarity	NPD7514	Phase 3

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