NPASS Compound

Structure

NPC472077 OpenBabel07101718282D 44 49 0 0 1 0 0 0 0 0999 V2000 -2.2938 2.4164 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3282 -2.1821 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8282 -3.0481 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4255 -1.2694 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4345 -1.1352 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9386 -0.2626 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8806 -0.4739 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4311 -0.8262 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1113 -1.5593 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1266 -1.6525 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9622 -4.5481 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5605 -0.7515 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0962 -4.0481 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9507 0.8137 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1653 -2.6828 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3792 0.9253 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2923 -4.0481 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1596 1.4254 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.1294 -1.7272 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4339 -0.9010 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8760 1.1929 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3836 1.5719 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2923 -3.0481 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.9622 -2.5481 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.8282 -4.0481 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.2343 1.0462 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.4263 -2.5481 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.5603 -3.0481 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.6670 0.5812 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.5603 -4.0481 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.8282 -3.0481 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0463 -0.3441 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9972 0.0747 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.0962 -3.0481 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.0102 2.1839 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3089 2.5691 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.1584 -2.5481 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.4263 -1.5481 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.6943 -2.5481 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5301 -2.1472 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.4263 -4.5481 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.6943 -4.5481 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.6580 0.4470 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 31 1 0 0 0 0 3 31 1 0 0 0 0 4 32 1 0 0 0 0 5 32 1 0 0 0 0 6 33 1 0 0 0 0 8 9 1 0 0 0 0 8 20 2 0 0 0 0 9 24 1 0 0 0 0 10 12 1 0 0 0 0 10 19 2 0 0 0 0 11 13 1 0 0 0 0 11 25 1 0 0 0 0 12 33 1 0 0 0 0 13 35 1 0 0 0 0 14 18 1 0 0 0 0 14 21 1 0 0 0 0 15 19 1 0 0 0 0 15 35 1 0 0 0 0 16 22 1 0 0 0 0 16 34 1 0 0 0 0 17 23 1 0 0 0 0 17 42 1 0 0 0 0 18 1 1 1 0 0 0 18 26 1 0 0 0 0 19 20 1 0 0 0 0 20 34 1 0 0 0 0 21 36 2 0 0 0 0 22 26 1 0 0 0 0 22 37 2 0 0 0 0 23 27 1 0 0 0 0 23 38 1 6 0 0 0 24 31 1 0 0 0 0 24 35 1 1 0 0 0 25 31 1 0 0 0 0 25 43 1 1 0 0 0 26 33 1 1 0 0 0 27 28 1 0 0 0 0 27 39 1 1 0 0 0 28 30 1 0 0 0 0 28 40 1 6 0 0 0 29 21 1 1 0 0 0 29 32 1 0 0 0 0 29 44 1 0 0 0 0 30 42 1 0 0 0 0 30 43 1 1 0 0 0 32 44 1 0 0 0 0 33 34 1 1 0 0 0 34 7 1 6 0 0 0 35 41 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	616.36
Volume:	631.143
LogP:	3.193
LogD:	1.886
LogS:	-4.132
# Rotatable Bonds:	6
TPSA:	146.05
# H-Bond Aceptor:	9
# H-Bond Donor:	4
# Rings:	6
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.33
Synthetic Accessibility Score:	5.851
Fsp3:	0.829
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:	-4.93
MDCK Permeability:	2.0328863683971576e-05
Pgp-inhibitor:	1.0
Pgp-substrate:	0.991
Human Intestinal Absorption (HIA):	0.22
20% Bioavailability (F20%):	0.05
30% Bioavailability (F30%):	0.266

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.087
Plasma Protein Binding (PPB):	76.04320526123047%
Volume Distribution (VD):	0.487
Pgp-substrate:	11.569845199584961%

ADMET: Metabolism

CYP1A2-inhibitor:	0.001
CYP1A2-substrate:	0.134
CYP2C19-inhibitor:	0.007
CYP2C19-substrate:	0.779
CYP2C9-inhibitor:	0.021
CYP2C9-substrate:	0.036
CYP2D6-inhibitor:	0.003
CYP2D6-substrate:	0.18
CYP3A4-inhibitor:	0.136
CYP3A4-substrate:	0.317

ADMET: Excretion

Clearance (CL):	3.139
Half-life (T1/2):	0.444

ADMET: Toxicity

hERG Blockers:	0.095
Human Hepatotoxicity (H-HT):	0.298
Drug-inuced Liver Injury (DILI):	0.042
AMES Toxicity:	0.069
Rat Oral Acute Toxicity:	0.81
Maximum Recommended Daily Dose:	0.954
Skin Sensitization:	0.173
Carcinogencity:	0.709
Eye Corrosion:	0.003
Eye Irritation:	0.007
Respiratory Toxicity:	0.975

Download Data

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

Natural Product: NPC472077

Natural Product ID:	NPC472077
*Common Name:**	XFPBNXYKZXOJNP-FXDNHWGZSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	XFPBNXYKZXOJNP-FXDNHWGZSA-N
Standard InCHI:	InChI=1S/C35H52O9/c1-18(14-21(36)29-32(4,5)44-29)26-22(37)16-34(7)20-8-9-24-31(2,3)25(43-30-28(40)27(39)23(38)17-42-30)11-13-35(24,41)15-19(20)10-12-33(26,34)6/h8,10,18,23-30,38-41H,9,11-17H2,1-7H3/t18-,23-,24+,25+,26+,27+,28-,29+,30+,33-,34+,35+/m1/s1
SMILES:	O[C@H]1[C@H](O)CO[C@H]([C@@H]1O)O[C@H]1CC[C@]2([C@H](C1(C)C)CC=C1C(=CC[C@]3([C@@]1(C)CC(=O)[C@@H]3[C@@H](CC(=O)[C@@H]1OC1(C)C)C)C)C2)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3337546
PubChem CID:	n.a.
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
NPO31564	Cimicifuga foetida	n.a.	n.a.	n.a.	n.a.	aerial part	n.a.	PMID[19280146]
NPO31564	Cimicifuga foetida	n.a.	n.a.	n.a.	rhizomes	n.a.	n.a.	PMID[25136911]
NPO31564	Cimicifuga foetida	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[HerDing]
NPO31564	Cimicifuga foetida	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[TCM_Taiwan]

☑ 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	2
NON-MOLECULAR	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT83	Cell Line	MCF7	Homo sapiens	IC50	>	10000.0	nM	PMID[458728]
NPT165	Cell Line	HeLa	Homo sapiens	IC50	>	10000.0	nM	PMID[458728]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	10000.0	nM	PMID[458728]

☑ 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 NPC472077 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	258
0.1-0.2	1536
0.2-0.3	5092
0.3-0.4	10045
0.4-0.5	11965
0.5-0.6	7202
0.6-0.7	5305
0.7-0.8	1275
0.8-0.85	14
0.85-0.9	1
0.9-0.95	0
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC472078
0.9735	High Similarity	NPC472076
0.9735	High Similarity	NPC472075
0.8621	High Similarity	NPC130427
0.8583	High Similarity	NPC472257
0.8475	Intermediate Similarity	NPC474557
0.8475	Intermediate Similarity	NPC116024
0.8448	Intermediate Similarity	NPC475317
0.8448	Intermediate Similarity	NPC154856
0.8448	Intermediate Similarity	NPC52241
0.8376	Intermediate Similarity	NPC292196
0.8305	Intermediate Similarity	NPC210420
0.8305	Intermediate Similarity	NPC474265
0.8279	Intermediate Similarity	NPC471406
0.8205	Intermediate Similarity	NPC265655
0.8167	Intermediate Similarity	NPC473882
0.816	Intermediate Similarity	NPC130229
0.8136	Intermediate Similarity	NPC129340
0.812	Intermediate Similarity	NPC195708
0.8115	Intermediate Similarity	NPC86020
0.8115	Intermediate Similarity	NPC239293
0.8115	Intermediate Similarity	NPC475632
0.8103	Intermediate Similarity	NPC210178
0.8099	Intermediate Similarity	NPC473126
0.8099	Intermediate Similarity	NPC279638
0.8083	Intermediate Similarity	NPC260665
0.8083	Intermediate Similarity	NPC251309
0.8067	Intermediate Similarity	NPC250481
0.8067	Intermediate Similarity	NPC285410
0.8067	Intermediate Similarity	NPC263827
0.8051	Intermediate Similarity	NPC477069
0.8051	Intermediate Similarity	NPC477070
0.8051	Intermediate Similarity	NPC218853
0.8051	Intermediate Similarity	NPC118225
0.8017	Intermediate Similarity	NPC475163
0.8017	Intermediate Similarity	NPC220293
0.8017	Intermediate Similarity	NPC74727
0.8016	Intermediate Similarity	NPC475194
0.8	Intermediate Similarity	NPC233003
0.8	Intermediate Similarity	NPC216866
0.7984	Intermediate Similarity	NPC475187
0.7983	Intermediate Similarity	NPC101450
0.7983	Intermediate Similarity	NPC250956
0.7967	Intermediate Similarity	NPC473828
0.7967	Intermediate Similarity	NPC473617
0.7966	Intermediate Similarity	NPC295389
0.7953	Intermediate Similarity	NPC198714
0.7951	Intermediate Similarity	NPC31797
0.7949	Intermediate Similarity	NPC95243
0.7949	Intermediate Similarity	NPC63023
0.7949	Intermediate Similarity	NPC162033
0.7937	Intermediate Similarity	NPC238005
0.7937	Intermediate Similarity	NPC1980
0.7937	Intermediate Similarity	NPC141196
0.7934	Intermediate Similarity	NPC73455
0.7934	Intermediate Similarity	NPC200944
0.7923	Intermediate Similarity	NPC231240
0.792	Intermediate Similarity	NPC476544
0.792	Intermediate Similarity	NPC75417
0.792	Intermediate Similarity	NPC476545
0.792	Intermediate Similarity	NPC476543
0.7917	Intermediate Similarity	NPC269466
0.7917	Intermediate Similarity	NPC477073
0.7907	Intermediate Similarity	NPC476854
0.7899	Intermediate Similarity	NPC246205
0.7891	Intermediate Similarity	NPC42399
0.7881	Intermediate Similarity	NPC293512
0.7874	Intermediate Similarity	NPC177820
0.7874	Intermediate Similarity	NPC30188
0.7874	Intermediate Similarity	NPC476674
0.7863	Intermediate Similarity	NPC100955
0.7863	Intermediate Similarity	NPC121566
0.7863	Intermediate Similarity	NPC316915
0.7863	Intermediate Similarity	NPC223741
0.7857	Intermediate Similarity	NPC275343
0.7857	Intermediate Similarity	NPC156789
0.7851	Intermediate Similarity	NPC174836
0.7846	Intermediate Similarity	NPC476855
0.784	Intermediate Similarity	NPC476849
0.7836	Intermediate Similarity	NPC477233
0.7836	Intermediate Similarity	NPC477232
0.7833	Intermediate Similarity	NPC242611
0.7833	Intermediate Similarity	NPC90630
0.7833	Intermediate Similarity	NPC475243
0.7829	Intermediate Similarity	NPC168899
0.7829	Intermediate Similarity	NPC476859
0.7829	Intermediate Similarity	NPC476091
0.7829	Intermediate Similarity	NPC293623
0.7829	Intermediate Similarity	NPC188291
0.7829	Intermediate Similarity	NPC69273
0.7829	Intermediate Similarity	NPC476078
0.7823	Intermediate Similarity	NPC45475
0.7823	Intermediate Similarity	NPC297179
0.7823	Intermediate Similarity	NPC286347
0.7823	Intermediate Similarity	NPC234522
0.7815	Intermediate Similarity	NPC258323
0.7812	Intermediate Similarity	NPC181066
0.7812	Intermediate Similarity	NPC47113
0.7812	Intermediate Similarity	NPC222307
0.7812	Intermediate Similarity	NPC476673
0.7812	Intermediate Similarity	NPC469947
0.7812	Intermediate Similarity	NPC174367
0.7812	Intermediate Similarity	NPC104427
0.7807	Intermediate Similarity	NPC472074
0.7807	Intermediate Similarity	NPC472073
0.7805	Intermediate Similarity	NPC244127
0.7803	Intermediate Similarity	NPC478069
0.7797	Intermediate Similarity	NPC475494
0.7795	Intermediate Similarity	NPC476542
0.7795	Intermediate Similarity	NPC160084
0.7795	Intermediate Similarity	NPC41129
0.7787	Intermediate Similarity	NPC477074
0.7787	Intermediate Similarity	NPC477944
0.7787	Intermediate Similarity	NPC75167
0.7787	Intermediate Similarity	NPC73986
0.7787	Intermediate Similarity	NPC311592
0.7786	Intermediate Similarity	NPC473519
0.7786	Intermediate Similarity	NPC473805
0.7778	Intermediate Similarity	NPC475182
0.7778	Intermediate Similarity	NPC102822
0.7778	Intermediate Similarity	NPC477046
0.7778	Intermediate Similarity	NPC202051
0.7778	Intermediate Similarity	NPC42675
0.7769	Intermediate Similarity	NPC471407
0.7769	Intermediate Similarity	NPC272242
0.7769	Intermediate Similarity	NPC476851
0.7769	Intermediate Similarity	NPC31839
0.7769	Intermediate Similarity	NPC190837
0.7769	Intermediate Similarity	NPC207689
0.7769	Intermediate Similarity	NPC476966
0.776	Intermediate Similarity	NPC473884
0.776	Intermediate Similarity	NPC157868
0.776	Intermediate Similarity	NPC475171
0.776	Intermediate Similarity	NPC180550
0.776	Intermediate Similarity	NPC214484
0.776	Intermediate Similarity	NPC39211
0.776	Intermediate Similarity	NPC319570
0.776	Intermediate Similarity	NPC472949
0.776	Intermediate Similarity	NPC469945
0.776	Intermediate Similarity	NPC309780
0.776	Intermediate Similarity	NPC114441
0.776	Intermediate Similarity	NPC208381
0.776	Intermediate Similarity	NPC6377
0.776	Intermediate Similarity	NPC11551
0.776	Intermediate Similarity	NPC35405
0.776	Intermediate Similarity	NPC477071
0.7752	Intermediate Similarity	NPC305496
0.7752	Intermediate Similarity	NPC2757
0.7752	Intermediate Similarity	NPC292290
0.775	Intermediate Similarity	NPC475364
0.775	Intermediate Similarity	NPC8431
0.7742	Intermediate Similarity	NPC224121
0.7734	Intermediate Similarity	NPC470477
0.7734	Intermediate Similarity	NPC248202
0.7734	Intermediate Similarity	NPC6615
0.7734	Intermediate Similarity	NPC473474
0.7734	Intermediate Similarity	NPC7850
0.7727	Intermediate Similarity	NPC102015
0.7727	Intermediate Similarity	NPC475487
0.7724	Intermediate Similarity	NPC181145
0.7724	Intermediate Similarity	NPC477580
0.7724	Intermediate Similarity	NPC165439
0.7717	Intermediate Similarity	NPC107966
0.7717	Intermediate Similarity	NPC162574
0.7717	Intermediate Similarity	NPC471965
0.7717	Intermediate Similarity	NPC131824
0.7717	Intermediate Similarity	NPC40775
0.7717	Intermediate Similarity	NPC28532
0.7717	Intermediate Similarity	NPC249848
0.7717	Intermediate Similarity	NPC235438
0.7712	Intermediate Similarity	NPC187400
0.7712	Intermediate Similarity	NPC470885
0.7712	Intermediate Similarity	NPC221562
0.771	Intermediate Similarity	NPC476862
0.771	Intermediate Similarity	NPC241008
0.771	Intermediate Similarity	NPC173347
0.771	Intermediate Similarity	NPC473838
0.771	Intermediate Similarity	NPC476852
0.771	Intermediate Similarity	NPC475389
0.771	Intermediate Similarity	NPC476863
0.7705	Intermediate Similarity	NPC470543
0.7705	Intermediate Similarity	NPC212968
0.7705	Intermediate Similarity	NPC243572
0.7705	Intermediate Similarity	NPC1046
0.7705	Intermediate Similarity	NPC100383
0.7705	Intermediate Similarity	NPC37739
0.7705	Intermediate Similarity	NPC161434
0.7705	Intermediate Similarity	NPC195132
0.7705	Intermediate Similarity	NPC80843
0.7705	Intermediate Similarity	NPC125923
0.7705	Intermediate Similarity	NPC46388
0.7705	Intermediate Similarity	NPC64106
0.7705	Intermediate Similarity	NPC48249
0.7705	Intermediate Similarity	NPC65590
0.7698	Intermediate Similarity	NPC129393
0.7698	Intermediate Similarity	NPC294112
0.7698	Intermediate Similarity	NPC241192
0.7692	Intermediate Similarity	NPC245094
0.7692	Intermediate Similarity	NPC311534
0.7692	Intermediate Similarity	NPC270109

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 NPC472077 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	225
0.1-0.2	1720
0.2-0.3	4067
0.3-0.4	2089
0.4-0.5	582
0.5-0.6	253
0.6-0.7	178
0.7-0.8	36
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
0.7857	Intermediate Similarity	NPD6370	Approved
0.7752	Intermediate Similarity	NPD8293	Discontinued
0.7698	Intermediate Similarity	NPD6054	Approved
0.7698	Intermediate Similarity	NPD6059	Approved
0.7692	Intermediate Similarity	NPD7736	Approved
0.7656	Intermediate Similarity	NPD8328	Phase 3
0.76	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7583	Intermediate Similarity	NPD6412	Phase 2
0.75	Intermediate Similarity	NPD6015	Approved
0.75	Intermediate Similarity	NPD6016	Approved
0.7462	Intermediate Similarity	NPD7492	Approved
0.7442	Intermediate Similarity	NPD5988	Approved
0.7422	Intermediate Similarity	NPD6319	Approved
0.7419	Intermediate Similarity	NPD8297	Approved
0.7419	Intermediate Similarity	NPD6882	Approved
0.7405	Intermediate Similarity	NPD6616	Approved
0.7348	Intermediate Similarity	NPD7078	Approved
0.7317	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7239	Intermediate Similarity	NPD7319	Approved
0.7213	Intermediate Similarity	NPD6675	Approved
0.7213	Intermediate Similarity	NPD7128	Approved
0.7213	Intermediate Similarity	NPD6402	Approved
0.7213	Intermediate Similarity	NPD5739	Approved
0.7188	Intermediate Similarity	NPD7115	Discovery
0.7188	Intermediate Similarity	NPD6009	Approved
0.7177	Intermediate Similarity	NPD6373	Approved
0.7177	Intermediate Similarity	NPD6372	Approved
0.7164	Intermediate Similarity	NPD6033	Approved
0.7143	Intermediate Similarity	NPD7507	Approved
0.7099	Intermediate Similarity	NPD8517	Approved
0.7099	Intermediate Similarity	NPD8515	Approved
0.7099	Intermediate Similarity	NPD8513	Phase 3
0.7099	Intermediate Similarity	NPD8516	Approved
0.7097	Intermediate Similarity	NPD6881	Approved
0.7097	Intermediate Similarity	NPD7320	Approved
0.7097	Intermediate Similarity	NPD6899	Approved
0.7087	Intermediate Similarity	NPD8133	Approved
0.7063	Intermediate Similarity	NPD6650	Approved
0.7063	Intermediate Similarity	NPD6649	Approved
0.7063	Intermediate Similarity	NPD8130	Phase 1
0.7016	Intermediate Similarity	NPD5701	Approved
0.7016	Intermediate Similarity	NPD5697	Approved
0.7	Intermediate Similarity	NPD7327	Approved
0.7	Intermediate Similarity	NPD7328	Approved
0.6984	Remote Similarity	NPD4634	Approved
0.6984	Remote Similarity	NPD6883	Approved
0.6984	Remote Similarity	NPD7102	Approved
0.6984	Remote Similarity	NPD7290	Approved
0.697	Remote Similarity	NPD7503	Approved
0.697	Remote Similarity	NPD8033	Approved
0.696	Remote Similarity	NPD6686	Approved
0.6953	Remote Similarity	NPD4632	Approved
0.6947	Remote Similarity	NPD7516	Approved
0.6929	Remote Similarity	NPD6617	Approved
0.6929	Remote Similarity	NPD6847	Approved
0.6929	Remote Similarity	NPD6869	Approved
0.6917	Remote Similarity	NPD6083	Phase 2
0.6917	Remote Similarity	NPD4755	Approved
0.6917	Remote Similarity	NPD6084	Phase 2
0.6905	Remote Similarity	NPD6012	Approved
0.6905	Remote Similarity	NPD6013	Approved
0.6905	Remote Similarity	NPD6014	Approved
0.6894	Remote Similarity	NPD8377	Approved
0.6894	Remote Similarity	NPD8294	Approved
0.6866	Remote Similarity	NPD7604	Phase 2
0.6864	Remote Similarity	NPD6399	Phase 3
0.686	Remote Similarity	NPD5696	Approved
0.6842	Remote Similarity	NPD8296	Approved
0.6842	Remote Similarity	NPD8378	Approved
0.6842	Remote Similarity	NPD8379	Approved
0.6842	Remote Similarity	NPD8380	Approved
0.6842	Remote Similarity	NPD8335	Approved
0.6825	Remote Similarity	NPD6011	Approved
0.6825	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6803	Remote Similarity	NPD4700	Approved
0.6803	Remote Similarity	NPD4696	Approved
0.6803	Remote Similarity	NPD5286	Approved
0.6803	Remote Similarity	NPD5285	Approved
0.6797	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6754	Remote Similarity	NPD4786	Approved
0.675	Remote Similarity	NPD5695	Phase 3
0.6741	Remote Similarity	NPD6067	Discontinued
0.6716	Remote Similarity	NPD5983	Phase 2
0.6694	Remote Similarity	NPD5225	Approved
0.6694	Remote Similarity	NPD5211	Phase 2
0.6694	Remote Similarity	NPD5226	Approved
0.6694	Remote Similarity	NPD4633	Approved
0.6694	Remote Similarity	NPD5224	Approved
0.6691	Remote Similarity	NPD5956	Approved
0.6667	Remote Similarity	NPD6008	Approved
0.6667	Remote Similarity	NPD4767	Approved
0.6667	Remote Similarity	NPD4768	Approved
0.6642	Remote Similarity	NPD6336	Discontinued
0.6641	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.664	Remote Similarity	NPD5174	Approved
0.664	Remote Similarity	NPD5175	Approved
0.6639	Remote Similarity	NPD6411	Approved
0.6638	Remote Similarity	NPD5279	Phase 3
0.6613	Remote Similarity	NPD5223	Approved
0.6612	Remote Similarity	NPD4629	Approved
0.6612	Remote Similarity	NPD5210	Approved
0.661	Remote Similarity	NPD5328	Approved
0.661	Remote Similarity	NPD4753	Phase 2
0.6594	Remote Similarity	NPD8074	Phase 3
0.6591	Remote Similarity	NPD6274	Approved
0.6587	Remote Similarity	NPD5141	Approved
0.6587	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6583	Remote Similarity	NPD4202	Approved
0.6579	Remote Similarity	NPD3667	Approved
0.6567	Remote Similarity	NPD7101	Approved
0.6567	Remote Similarity	NPD7100	Approved
0.6562	Remote Similarity	NPD4729	Approved
0.6562	Remote Similarity	NPD4730	Approved
0.6557	Remote Similarity	NPD5222	Approved
0.6557	Remote Similarity	NPD4697	Phase 3
0.6557	Remote Similarity	NPD5221	Approved
0.6557	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6525	Remote Similarity	NPD5737	Approved
0.6525	Remote Similarity	NPD6672	Approved
0.6508	Remote Similarity	NPD4754	Approved
0.6504	Remote Similarity	NPD5173	Approved
0.65	Remote Similarity	NPD6050	Approved
0.65	Remote Similarity	NPD6079	Approved
0.6496	Remote Similarity	NPD3618	Phase 1
0.6493	Remote Similarity	NPD6335	Approved
0.6479	Remote Similarity	NPD8338	Approved
0.6471	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD6101	Approved
0.6471	Remote Similarity	NPD6909	Approved
0.6471	Remote Similarity	NPD6908	Approved
0.6462	Remote Similarity	NPD5251	Approved
0.6462	Remote Similarity	NPD5248	Approved
0.6462	Remote Similarity	NPD5250	Approved
0.6462	Remote Similarity	NPD5249	Phase 3
0.6462	Remote Similarity	NPD5247	Approved
0.6462	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6434	Remote Similarity	NPD5128	Approved
0.6429	Remote Similarity	NPD8337	Approved
0.6429	Remote Similarity	NPD8336	Approved
0.6418	Remote Similarity	NPD6317	Approved
0.6417	Remote Similarity	NPD5692	Phase 3
0.6412	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6408	Remote Similarity	NPD7260	Phase 2
0.6393	Remote Similarity	NPD7748	Approved
0.6371	Remote Similarity	NPD7902	Approved
0.637	Remote Similarity	NPD6314	Approved
0.637	Remote Similarity	NPD6313	Approved
0.6364	Remote Similarity	NPD8034	Phase 2
0.6364	Remote Similarity	NPD8035	Phase 2
0.6364	Remote Similarity	NPD5694	Approved
0.6356	Remote Similarity	NPD6098	Approved
0.6356	Remote Similarity	NPD4694	Approved
0.6356	Remote Similarity	NPD5280	Approved
0.635	Remote Similarity	NPD6921	Approved
0.6343	Remote Similarity	NPD6868	Approved
0.6336	Remote Similarity	NPD6371	Approved
0.6333	Remote Similarity	NPD6904	Approved
0.6333	Remote Similarity	NPD6673	Approved
0.6333	Remote Similarity	NPD6080	Approved
0.632	Remote Similarity	NPD7638	Approved
0.6303	Remote Similarity	NPD7524	Approved
0.6288	Remote Similarity	NPD5216	Approved
0.6288	Remote Similarity	NPD5215	Approved
0.6288	Remote Similarity	NPD5217	Approved
0.6271	Remote Similarity	NPD5329	Approved
0.627	Remote Similarity	NPD7640	Approved
0.627	Remote Similarity	NPD7639	Approved
0.6265	Remote Similarity	NPD7799	Discontinued
0.6261	Remote Similarity	NPD7525	Registered
0.626	Remote Similarity	NPD5282	Discontinued
0.6232	Remote Similarity	NPD8274	Clinical (unspecified phase)
0.6231	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6231	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.623	Remote Similarity	NPD7515	Phase 2
0.623	Remote Similarity	NPD7983	Approved
0.623	Remote Similarity	NPD7637	Suspended
0.623	Remote Similarity	NPD5281	Approved
0.623	Remote Similarity	NPD5284	Approved
0.6218	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6212	Remote Similarity	NPD5135	Approved
0.6212	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6212	Remote Similarity	NPD5169	Approved
0.621	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6204	Remote Similarity	NPD4522	Approved
0.619	Remote Similarity	NPD4225	Approved
0.6187	Remote Similarity	NPD8080	Discontinued
0.6186	Remote Similarity	NPD3665	Phase 1
0.6186	Remote Similarity	NPD3666	Approved
0.6186	Remote Similarity	NPD4197	Approved
0.6186	Remote Similarity	NPD3668	Phase 3
0.6186	Remote Similarity	NPD3133	Approved
0.6186	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6179	Remote Similarity	NPD5778	Approved
0.6179	Remote Similarity	NPD5779	Approved
0.6165	Remote Similarity	NPD5127	Approved
0.6148	Remote Similarity	NPD6698	Approved
0.6148	Remote Similarity	NPD46	Approved
0.6138	Remote Similarity	NPD6845	Suspended
0.6134	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6129	Remote Similarity	NPD7901	Clinical (unspecified phase)

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