NPASS Compound

Structure

NPC309398 OpenBabel07101718282D 57 60 0 0 1 0 0 0 0 0999 V2000 -2.7542 4.0397 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5762 -0.1669 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6366 -0.2373 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8239 1.1423 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2832 4.2134 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4061 4.5576 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3197 0.8059 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6788 1.4965 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9707 2.6046 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3478 -0.1692 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4133 2.9347 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0320 3.3457 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5882 2.2892 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3450 0.6755 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8668 3.0595 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8641 1.2717 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1761 2.0311 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0808 0.2467 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8349 1.0594 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5191 3.1545 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4855 0.5298 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 3.2573 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0320 0.4050 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6838 3.1001 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.9324 1.4122 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3857 2.9497 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5191 0.5962 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6565 2.4297 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.0808 3.5040 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.5590 0.0419 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.4133 0.8160 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.8349 2.6913 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0582 0.7765 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.4515 2.0084 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8668 1.3903 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0001 1.5951 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6499 2.2468 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0454 0.6116 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5465 3.6260 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4011 0.5962 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 3.7507 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.5465 0.1247 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.4623 2.5694 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.2098 -0.0446 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.1073 2.8855 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7671 1.6680 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.9318 1.4546 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.5795 3.1863 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0178 4.6927 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8412 -0.7702 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.3832 1.8680 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.6571 0.4717 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.0691 1.6930 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.0001 2.1556 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.1286 1.7160 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5590 3.7088 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 2 38 1 0 0 0 0 3 38 1 0 0 0 0 4 38 1 0 0 0 0 5 39 1 0 0 0 0 6 39 1 0 0 0 0 7 40 1 0 0 0 0 8 40 1 0 0 0 0 9 51 1 0 0 0 0 10 52 1 0 0 0 0 11 12 2 0 0 0 0 12 39 1 0 0 0 0 13 25 1 0 0 0 0 13 28 1 0 0 0 0 14 25 1 0 0 0 0 15 26 1 0 0 0 0 16 25 2 0 0 0 0 16 34 1 0 0 0 0 17 26 2 0 0 0 0 17 35 1 0 0 0 0 18 27 1 0 0 0 0 19 27 1 0 0 0 0 19 36 1 0 0 0 0 20 29 1 0 0 0 0 20 32 1 0 0 0 0 21 30 1 0 0 0 0 21 33 1 0 0 0 0 22 26 1 0 0 0 0 22 41 1 0 0 0 0 23 31 1 0 0 0 0 23 42 1 0 0 0 0 24 1 1 6 0 0 0 24 43 1 0 0 0 0 27 44 1 1 0 0 0 28 11 1 1 0 0 0 28 53 1 0 0 0 0 29 15 1 6 0 0 0 29 56 1 0 0 0 0 30 18 1 6 0 0 0 30 57 1 0 0 0 0 31 14 1 1 0 0 0 31 53 1 0 0 0 0 32 24 1 1 0 0 0 32 54 1 0 0 0 0 33 40 1 0 0 0 0 33 55 1 6 0 0 0 34 45 2 0 0 0 0 34 51 1 0 0 0 0 35 46 2 0 0 0 0 35 52 1 0 0 0 0 36 47 2 0 0 0 0 36 54 1 0 0 0 0 37 38 1 0 0 0 0 37 48 2 0 0 0 0 37 55 1 0 0 0 0 39 41 1 0 0 0 0 40 42 1 0 0 0 0 41 49 1 6 0 0 0 41 56 1 0 0 0 0 42 50 1 1 0 0 0 42 57 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	808.42
Volume:	814.16
LogP:	3.987
LogD:	2.029
LogS:	-4.938
# Rotatable Bonds:	9
TPSA:	213.81
# H-Bond Aceptor:	15
# H-Bond Donor:	4
# Rings:	4
# Heavy Atoms:	15

MedChem Properties

QED Drug-Likeness Score:	0.134
Synthetic Accessibility Score:	7.73
Fsp3:	0.762
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:	-5.306
MDCK Permeability:	0.00015890883514657617
Pgp-inhibitor:	0.987
Pgp-substrate:	0.999
Human Intestinal Absorption (HIA):	0.305
20% Bioavailability (F20%):	0.894
30% Bioavailability (F30%):	0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.013
Plasma Protein Binding (PPB):	77.80463409423828%
Volume Distribution (VD):	1.219
Pgp-substrate:	9.122817993164062%

ADMET: Metabolism

CYP1A2-inhibitor:	0.001
CYP1A2-substrate:	0.059
CYP2C19-inhibitor:	0.122
CYP2C19-substrate:	0.604
CYP2C9-inhibitor:	0.525
CYP2C9-substrate:	0.024
CYP2D6-inhibitor:	0.002
CYP2D6-substrate:	0.052
CYP3A4-inhibitor:	0.929
CYP3A4-substrate:	0.929

ADMET: Excretion

Clearance (CL):	1.934
Half-life (T1/2):	0.21

ADMET: Toxicity

hERG Blockers:	0.764
Human Hepatotoxicity (H-HT):	0.94
Drug-inuced Liver Injury (DILI):	0.902
AMES Toxicity:	0.85
Rat Oral Acute Toxicity:	0.429
Maximum Recommended Daily Dose:	1.0
Skin Sensitization:	0.78
Carcinogencity:	0.111
Eye Corrosion:	0.003
Eye Irritation:	0.008
Respiratory Toxicity:	0.747

Download Data

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

Natural Product: NPC309398

Natural Product ID:	NPC309398
*Common Name:**	Bryostatin 10
IUPAC Name:	n.a.
Synonyms:	Bryostatin 10
Standard InCHIKey:	AVJAOOKIOFJJOC-VADSYKNVSA-N
Standard InCHI:	InChI=1S/C42H64O15/c1-24(43)32-20-29-15-26(17-35(46)52-10)22-41(49,56-29)39(5,6)12-11-28-13-25(16-34(45)51-9)14-31(53-28)23-42(50)40(7,8)33(55-37(48)38(2,3)4)21-30(57-42)18-27(44)19-36(47)54-32/h11-12,16-17,24,27-33,43-44,49-50H,13-15,18-23H2,1-10H3/b12-11+,25-16+,26-17+/t24-,27-,28+,29+,30-,31+,32-,33+,41-,42+/m1/s1
SMILES:	C[C@H]([C@H]1C[C@@H]2C/C(=CC(=O)OC)/C[C@@](C(C)(C)/C=C/[C@H]3C/C(=CC(=O)OC)/C[C@@H](C[C@]4(C(C)(C)[C@H](C[C@@H](C[C@H](CC(=O)O1)O)O4)OC(=O)C(C)(C)C)O)O3)(O)O2)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL501262
PubChem CID:	9962496
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000147] Macrolides and analogues

*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
NPO11979	Bugula neritina	Species	Bugulidae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1021/ja00388a092]
NPO11979	Bugula neritina	Species	Bugulidae	Eukaryota	n.a.	South China Sea	n.a.	PMID[25932671]
NPO11979	Bugula neritina	Species	Bugulidae	Eukaryota	n.a.	Gulf of Aomori, Japan	n.a.	PMID[8691208]
NPO11979	Bugula neritina	Species	Bugulidae	Eukaryota	n.a.	n.a.	n.a.	PMID[8882431]
NPO11979	Bugula neritina	Species	Bugulidae	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
ED50	2
Ki	1
Others	1

Activity Type	# Activity
Cell Line	1
Individual Protein	1
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT168	Cell Line	P388	Mus musculus	ED50	=	0.0018	ug ml-1	PMID[466563]
NPT182	Individual Protein	Protein kinase C alpha	Homo sapiens	Ki	=	1.56	nM	PMID[466564]
NPT2	Others	Unspecified		ED50	=	0.16	ug ml-1	PMID[466563]
NPT2	Others	Unspecified		Activity	=	1141.0	pmol/hr	PMID[466563]

☑ 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 NPC309398 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	219
0.1-0.2	1244
0.2-0.3	3932
0.3-0.4	7164
0.4-0.5	12994
0.5-0.6	9156
0.6-0.7	6131
0.7-0.8	1794
0.8-0.85	52
0.85-0.9	1
0.9-0.95	2
0.95-1	8

Similarity Score	Similarity Level	Natural Product ID
0.9794	High Similarity	NPC476740
0.9794	High Similarity	NPC476738
0.9792	High Similarity	NPC474581
0.9792	High Similarity	NPC473816
0.9792	High Similarity	NPC475367
0.9596	High Similarity	NPC193765
0.94	High Similarity	NPC473807
0.8571	High Similarity	NPC315836
0.8571	High Similarity	NPC313668
0.8416	Intermediate Similarity	NPC308567
0.8416	Intermediate Similarity	NPC187761
0.8416	Intermediate Similarity	NPC255592
0.8416	Intermediate Similarity	NPC83895
0.8416	Intermediate Similarity	NPC261377
0.84	Intermediate Similarity	NPC143446
0.8365	Intermediate Similarity	NPC472748
0.835	Intermediate Similarity	NPC473596
0.8317	Intermediate Similarity	NPC40812
0.8286	Intermediate Similarity	NPC472749
0.8286	Intermediate Similarity	NPC472751
0.8269	Intermediate Similarity	NPC472747
0.8269	Intermediate Similarity	NPC472750
0.8218	Intermediate Similarity	NPC255410
0.82	Intermediate Similarity	NPC71589
0.819	Intermediate Similarity	NPC469869
0.8173	Intermediate Similarity	NPC313569
0.8173	Intermediate Similarity	NPC472754
0.8148	Intermediate Similarity	NPC83005
0.8137	Intermediate Similarity	NPC120299
0.8125	Intermediate Similarity	NPC13710
0.8119	Intermediate Similarity	NPC300710
0.81	Intermediate Similarity	NPC320089
0.8081	Intermediate Similarity	NPC313670
0.8077	Intermediate Similarity	NPC472753
0.807	Intermediate Similarity	NPC473228
0.807	Intermediate Similarity	NPC470829
0.8058	Intermediate Similarity	NPC475653
0.802	Intermediate Similarity	NPC294293
0.8	Intermediate Similarity	NPC470379
0.8	Intermediate Similarity	NPC472199
0.8	Intermediate Similarity	NPC470373
0.7982	Intermediate Similarity	NPC476127
0.7982	Intermediate Similarity	NPC476150
0.7982	Intermediate Similarity	NPC48692
0.7963	Intermediate Similarity	NPC392
0.7963	Intermediate Similarity	NPC177524
0.7963	Intermediate Similarity	NPC219900
0.7961	Intermediate Similarity	NPC266842
0.7928	Intermediate Similarity	NPC75167
0.7928	Intermediate Similarity	NPC311592
0.7925	Intermediate Similarity	NPC472755
0.7921	Intermediate Similarity	NPC472195
0.7921	Intermediate Similarity	NPC478037
0.7921	Intermediate Similarity	NPC472196
0.7921	Intermediate Similarity	NPC478036
0.7921	Intermediate Similarity	NPC238090
0.7913	Intermediate Similarity	NPC170880
0.7913	Intermediate Similarity	NPC469812
0.7913	Intermediate Similarity	NPC476204
0.7913	Intermediate Similarity	NPC183353
0.7913	Intermediate Similarity	NPC170084
0.7909	Intermediate Similarity	NPC126897
0.7909	Intermediate Similarity	NPC297945
0.7905	Intermediate Similarity	NPC475655
0.7905	Intermediate Similarity	NPC57586
0.7905	Intermediate Similarity	NPC2313
0.7905	Intermediate Similarity	NPC154132
0.7905	Intermediate Similarity	NPC471637
0.7905	Intermediate Similarity	NPC475157
0.7895	Intermediate Similarity	NPC77689
0.7895	Intermediate Similarity	NPC473839
0.7895	Intermediate Similarity	NPC211093
0.7895	Intermediate Similarity	NPC473636
0.7885	Intermediate Similarity	NPC40182
0.7885	Intermediate Similarity	NPC161855
0.7885	Intermediate Similarity	NPC198422
0.7876	Intermediate Similarity	NPC474483
0.7876	Intermediate Similarity	NPC473968
0.7864	Intermediate Similarity	NPC475525
0.7864	Intermediate Similarity	NPC475540
0.7864	Intermediate Similarity	NPC475375
0.7864	Intermediate Similarity	NPC473765
0.7864	Intermediate Similarity	NPC473605
0.7864	Intermediate Similarity	NPC475593
0.7864	Intermediate Similarity	NPC476066
0.7864	Intermediate Similarity	NPC475164
0.7864	Intermediate Similarity	NPC475241
0.7863	Intermediate Similarity	NPC318135
0.7857	Intermediate Similarity	NPC181145
0.785	Intermediate Similarity	NPC203659
0.785	Intermediate Similarity	NPC470519
0.785	Intermediate Similarity	NPC231271
0.785	Intermediate Similarity	NPC472756
0.7843	Intermediate Similarity	NPC472198
0.7843	Intermediate Similarity	NPC159698
0.783	Intermediate Similarity	NPC201191
0.7822	Intermediate Similarity	NPC472197
0.7815	Intermediate Similarity	NPC245094
0.7807	Intermediate Similarity	NPC475309
0.7788	Intermediate Similarity	NPC44170
0.7788	Intermediate Similarity	NPC475332
0.7788	Intermediate Similarity	NPC278506
0.7778	Intermediate Similarity	NPC86005
0.7778	Intermediate Similarity	NPC199382
0.7778	Intermediate Similarity	NPC477959
0.7767	Intermediate Similarity	NPC36954
0.7757	Intermediate Similarity	NPC197736
0.7757	Intermediate Similarity	NPC4620
0.7757	Intermediate Similarity	NPC110989
0.7755	Intermediate Similarity	NPC471494
0.775	Intermediate Similarity	NPC470912
0.7745	Intermediate Similarity	NPC476300
0.7739	Intermediate Similarity	NPC475775
0.7739	Intermediate Similarity	NPC476529
0.7719	Intermediate Similarity	NPC475809
0.7719	Intermediate Similarity	NPC134430
0.7714	Intermediate Similarity	NPC56071
0.7714	Intermediate Similarity	NPC70733
0.7712	Intermediate Similarity	NPC470922
0.7705	Intermediate Similarity	NPC225791
0.77	Intermediate Similarity	NPC89001
0.7699	Intermediate Similarity	NPC110861
0.7692	Intermediate Similarity	NPC165332
0.7692	Intermediate Similarity	NPC195645
0.7692	Intermediate Similarity	NPC473291
0.7692	Intermediate Similarity	NPC180722
0.7686	Intermediate Similarity	NPC477197
0.7685	Intermediate Similarity	NPC220964
0.7685	Intermediate Similarity	NPC475676
0.7679	Intermediate Similarity	NPC174836
0.7677	Intermediate Similarity	NPC47937
0.7677	Intermediate Similarity	NPC311163
0.7672	Intermediate Similarity	NPC109607
0.7672	Intermediate Similarity	NPC107338
0.767	Intermediate Similarity	NPC477348
0.767	Intermediate Similarity	NPC477345
0.767	Intermediate Similarity	NPC238264
0.767	Intermediate Similarity	NPC256368
0.7667	Intermediate Similarity	NPC112492
0.7667	Intermediate Similarity	NPC472269
0.7667	Intermediate Similarity	NPC477075
0.7667	Intermediate Similarity	NPC329923
0.7667	Intermediate Similarity	NPC472270
0.7667	Intermediate Similarity	NPC477078
0.7667	Intermediate Similarity	NPC23020
0.7667	Intermediate Similarity	NPC472268
0.7667	Intermediate Similarity	NPC475281
0.7664	Intermediate Similarity	NPC149371
0.7664	Intermediate Similarity	NPC474709
0.7664	Intermediate Similarity	NPC225353
0.7652	Intermediate Similarity	NPC109603
0.7652	Intermediate Similarity	NPC473617
0.7652	Intermediate Similarity	NPC473828
0.7652	Intermediate Similarity	NPC474286
0.7652	Intermediate Similarity	NPC475130
0.7652	Intermediate Similarity	NPC93688
0.7647	Intermediate Similarity	NPC477349
0.7647	Intermediate Similarity	NPC476084
0.7647	Intermediate Similarity	NPC30515
0.7647	Intermediate Similarity	NPC184463
0.7647	Intermediate Similarity	NPC476075
0.7642	Intermediate Similarity	NPC469870
0.7642	Intermediate Similarity	NPC469871
0.7636	Intermediate Similarity	NPC55972
0.7636	Intermediate Similarity	NPC327286
0.7636	Intermediate Similarity	NPC475960
0.7636	Intermediate Similarity	NPC169888
0.7632	Intermediate Similarity	NPC268954
0.7627	Intermediate Similarity	NPC315783
0.7624	Intermediate Similarity	NPC477011
0.7624	Intermediate Similarity	NPC477016
0.7624	Intermediate Similarity	NPC477017
0.7623	Intermediate Similarity	NPC277212
0.7623	Intermediate Similarity	NPC30279
0.7623	Intermediate Similarity	NPC192765
0.7623	Intermediate Similarity	NPC473918
0.7623	Intermediate Similarity	NPC476776
0.7623	Intermediate Similarity	NPC312650
0.7623	Intermediate Similarity	NPC46823
0.7623	Intermediate Similarity	NPC178264
0.7623	Intermediate Similarity	NPC71391
0.7619	Intermediate Similarity	NPC134454
0.7619	Intermediate Similarity	NPC17326
0.7619	Intermediate Similarity	NPC472290
0.7615	Intermediate Similarity	NPC315070
0.7611	Intermediate Similarity	NPC264153
0.7603	Intermediate Similarity	NPC141600
0.7603	Intermediate Similarity	NPC470518
0.7603	Intermediate Similarity	NPC47995
0.7603	Intermediate Similarity	NPC269484
0.7603	Intermediate Similarity	NPC477079
0.7603	Intermediate Similarity	NPC477196
0.7603	Intermediate Similarity	NPC252289
0.7603	Intermediate Similarity	NPC280029
0.7603	Intermediate Similarity	NPC244296
0.7603	Intermediate Similarity	NPC107536
0.7603	Intermediate Similarity	NPC305793
0.7603	Intermediate Similarity	NPC82380
0.7603	Intermediate Similarity	NPC472267
0.7603	Intermediate Similarity	NPC470913

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 NPC309398 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	195
0.1-0.2	1451
0.2-0.3	3512
0.3-0.4	2501
0.4-0.5	969
0.5-0.6	368
0.6-0.7	122
0.7-0.8	31
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8265	Intermediate Similarity	NPD46	Approved
0.8265	Intermediate Similarity	NPD6698	Approved
0.8182	Intermediate Similarity	NPD7983	Approved
0.7963	Intermediate Similarity	NPD6686	Approved
0.7913	Intermediate Similarity	NPD8513	Phase 3
0.7913	Intermediate Similarity	NPD8516	Approved
0.7913	Intermediate Similarity	NPD8517	Approved
0.7913	Intermediate Similarity	NPD8515	Approved
0.7909	Intermediate Similarity	NPD8413	Clinical (unspecified phase)
0.7885	Intermediate Similarity	NPD8029	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD7839	Suspended
0.7627	Intermediate Similarity	NPD7830	Approved
0.7627	Intermediate Similarity	NPD7829	Approved
0.7549	Intermediate Similarity	NPD7838	Discovery
0.7438	Intermediate Similarity	NPD8074	Phase 3
0.7333	Intermediate Similarity	NPD8328	Phase 3
0.7317	Intermediate Similarity	NPD7319	Approved
0.7308	Intermediate Similarity	NPD6411	Approved
0.7258	Intermediate Similarity	NPD8390	Approved
0.7258	Intermediate Similarity	NPD8392	Approved
0.7258	Intermediate Similarity	NPD8391	Approved
0.7238	Intermediate Similarity	NPD5778	Approved
0.7238	Intermediate Similarity	NPD5779	Approved
0.7232	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7213	Intermediate Similarity	NPD7507	Approved
0.7213	Intermediate Similarity	NPD8451	Approved
0.7193	Intermediate Similarity	NPD6371	Approved
0.7167	Intermediate Similarity	NPD8444	Approved
0.7154	Intermediate Similarity	NPD8448	Approved
0.7119	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD6101	Approved
0.7103	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7049	Intermediate Similarity	NPD7642	Approved
0.7018	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7009	Intermediate Similarity	NPD8133	Approved
0.6992	Remote Similarity	NPD8299	Approved
0.6992	Remote Similarity	NPD8340	Approved
0.6992	Remote Similarity	NPD8342	Approved
0.6992	Remote Similarity	NPD8341	Approved
0.6942	Remote Similarity	NPD8294	Approved
0.6942	Remote Similarity	NPD8377	Approved
0.693	Remote Similarity	NPD6412	Phase 2
0.6909	Remote Similarity	NPD4225	Approved
0.6887	Remote Similarity	NPD5785	Approved
0.6885	Remote Similarity	NPD8296	Approved
0.6885	Remote Similarity	NPD8335	Approved
0.6885	Remote Similarity	NPD8033	Approved
0.6885	Remote Similarity	NPD8380	Approved
0.6885	Remote Similarity	NPD8378	Approved
0.6885	Remote Similarity	NPD8379	Approved
0.6833	Remote Similarity	NPD7115	Discovery
0.6803	Remote Similarity	NPD6319	Approved
0.6796	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6794	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.678	Remote Similarity	NPD6053	Discontinued
0.6777	Remote Similarity	NPD7641	Discontinued
0.6769	Remote Similarity	NPD8415	Approved
0.6757	Remote Similarity	NPD7638	Approved
0.672	Remote Similarity	NPD7492	Approved
0.6718	Remote Similarity	NPD8387	Clinical (unspecified phase)
0.6697	Remote Similarity	NPD5282	Discontinued
0.6696	Remote Similarity	NPD7640	Approved
0.6696	Remote Similarity	NPD7639	Approved
0.6694	Remote Similarity	NPD8080	Discontinued
0.6694	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.6693	Remote Similarity	NPD7736	Approved
0.6667	Remote Similarity	NPD6616	Approved
0.6667	Remote Similarity	NPD6054	Approved
0.6667	Remote Similarity	NPD7637	Suspended
0.6667	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6639	Remote Similarity	NPD7327	Approved
0.6639	Remote Similarity	NPD7328	Approved
0.6639	Remote Similarity	NPD8297	Approved
0.6637	Remote Similarity	NPD5344	Discontinued
0.6614	Remote Similarity	NPD7078	Approved
0.6614	Remote Similarity	NPD8293	Discontinued
0.6613	Remote Similarity	NPD8269	Approved
0.6613	Remote Similarity	NPD8267	Approved
0.6613	Remote Similarity	NPD8266	Approved
0.6613	Remote Similarity	NPD8268	Approved
0.6613	Remote Similarity	NPD7503	Approved
0.6585	Remote Similarity	NPD7516	Approved
0.6571	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6566	Remote Similarity	NPD8039	Approved
0.656	Remote Similarity	NPD6370	Approved
0.6538	Remote Similarity	NPD7260	Phase 2
0.6538	Remote Similarity	NPD7154	Phase 3
0.6535	Remote Similarity	NPD8273	Phase 1
0.6532	Remote Similarity	NPD6059	Approved
0.6509	Remote Similarity	NPD5786	Approved
0.65	Remote Similarity	NPD6882	Approved
0.648	Remote Similarity	NPD6015	Approved
0.648	Remote Similarity	NPD6921	Approved
0.648	Remote Similarity	NPD6016	Approved
0.648	Remote Similarity	NPD8274	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6446	Remote Similarity	NPD4632	Approved
0.6442	Remote Similarity	NPD6435	Approved
0.6429	Remote Similarity	NPD5988	Approved
0.6423	Remote Similarity	NPD7500	Approved
0.6423	Remote Similarity	NPD6009	Approved
0.6415	Remote Similarity	NPD5363	Approved
0.6303	Remote Similarity	NPD6899	Approved
0.6303	Remote Similarity	NPD6881	Approved
0.6296	Remote Similarity	NPD4251	Approved
0.6296	Remote Similarity	NPD4250	Approved
0.6294	Remote Similarity	NPD8389	Clinical (unspecified phase)
0.6286	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6286	Remote Similarity	NPD4269	Approved
0.6286	Remote Similarity	NPD4270	Approved
0.6281	Remote Similarity	NPD6649	Approved
0.6281	Remote Similarity	NPD6650	Approved
0.6281	Remote Similarity	NPD8130	Phase 1
0.6271	Remote Similarity	NPD7128	Approved
0.6271	Remote Similarity	NPD5739	Approved
0.6271	Remote Similarity	NPD6402	Approved
0.6271	Remote Similarity	NPD6675	Approved
0.6261	Remote Similarity	NPD6648	Approved
0.625	Remote Similarity	NPD6373	Approved
0.625	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.625	Remote Similarity	NPD7748	Approved
0.625	Remote Similarity	NPD5368	Approved
0.625	Remote Similarity	NPD6372	Approved
0.6232	Remote Similarity	NPD8384	Approved
0.6228	Remote Similarity	NPD7902	Approved
0.6226	Remote Similarity	NPD5362	Discontinued
0.6218	Remote Similarity	NPD5697	Approved
0.6218	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6214	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6204	Remote Similarity	NPD4249	Approved
0.6198	Remote Similarity	NPD6421	Discontinued
0.6198	Remote Similarity	NPD4634	Approved
0.6198	Remote Similarity	NPD6883	Approved
0.6198	Remote Similarity	NPD7290	Approved
0.6198	Remote Similarity	NPD7102	Approved
0.619	Remote Similarity	NPD5369	Approved
0.6167	Remote Similarity	NPD7320	Approved
0.6161	Remote Similarity	NPD6399	Phase 3
0.6154	Remote Similarity	NPD7632	Discontinued
0.6148	Remote Similarity	NPD6617	Approved
0.6148	Remote Similarity	NPD6869	Approved
0.6148	Remote Similarity	NPD7116	Clinical (unspecified phase)
0.6148	Remote Similarity	NPD6847	Approved
0.6132	Remote Similarity	NPD5209	Approved
0.6124	Remote Similarity	NPD7604	Phase 2
0.6119	Remote Similarity	NPD6845	Suspended
0.6116	Remote Similarity	NPD6014	Approved
0.6116	Remote Similarity	NPD6013	Approved
0.6116	Remote Similarity	NPD6012	Approved
0.6111	Remote Similarity	NPD1694	Approved
0.6095	Remote Similarity	NPD4252	Approved
0.6095	Remote Similarity	NPD4820	Approved
0.6095	Remote Similarity	NPD4822	Approved
0.6095	Remote Similarity	NPD4819	Approved
0.6095	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6095	Remote Similarity	NPD4821	Approved
0.6094	Remote Similarity	NPD5983	Phase 2
0.6087	Remote Similarity	NPD6084	Phase 2
0.6087	Remote Similarity	NPD6083	Phase 2
0.6083	Remote Similarity	NPD5701	Approved
0.6075	Remote Similarity	NPD6110	Phase 1
0.6071	Remote Similarity	NPD7515	Phase 2
0.6061	Remote Similarity	NPD8337	Approved
0.6061	Remote Similarity	NPD6033	Approved
0.6061	Remote Similarity	NPD8336	Approved
0.6058	Remote Similarity	NPD4268	Approved
0.6058	Remote Similarity	NPD4271	Approved
0.6055	Remote Similarity	NPD6422	Discontinued
0.6033	Remote Similarity	NPD6011	Approved
0.6031	Remote Similarity	NPD6336	Discontinued
0.602	Remote Similarity	NPD4247	Clinical (unspecified phase)
0.6017	Remote Similarity	NPD8138	Approved
0.6017	Remote Similarity	NPD8082	Approved
0.6017	Remote Similarity	NPD8086	Approved
0.6017	Remote Similarity	NPD8083	Approved
0.6017	Remote Similarity	NPD8139	Approved
0.6017	Remote Similarity	NPD8085	Approved
0.6017	Remote Similarity	NPD8084	Approved
0.6	Remote Similarity	NPD6008	Approved
0.6	Remote Similarity	NPD6010	Discontinued
0.6	Remote Similarity	NPD5048	Discontinued
0.6	Remote Similarity	NPD7329	Approved
0.5966	Remote Similarity	NPD8275	Approved
0.5966	Remote Similarity	NPD8276	Approved
0.5965	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.5965	Remote Similarity	NPD7900	Approved
0.5963	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.5929	Remote Similarity	NPD6079	Approved
0.5918	Remote Similarity	NPD7331	Phase 2
0.5917	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.5917	Remote Similarity	NPD8081	Approved
0.5913	Remote Similarity	NPD5695	Phase 3
0.5909	Remote Similarity	NPD5330	Approved
0.5909	Remote Similarity	NPD7521	Approved
0.5909	Remote Similarity	NPD6409	Approved
0.5909	Remote Similarity	NPD7146	Approved
0.5909	Remote Similarity	NPD7334	Approved
0.5909	Remote Similarity	NPD6684	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