NPASS Compound

Structure

NPC472076 OpenBabel07101719142D 45 49 0 0 1 0 0 0 0 0999 V2000 2.1800 -2.1485 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5539 1.7913 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5539 1.7913 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7019 0.7712 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0811 -0.1541 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7419 -1.8102 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8507 0.5257 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 -2.4060 1.0488 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8678 -1.8019 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9199 -0.5747 0.0000 C 0 0 0 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 -4.0539 -1.0747 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2396 -0.7783 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4060 -1.1982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6117 0.7911 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.5180 -1.0747 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3143 -1.1575 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.4311 -0.9757 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9972 -0.0747 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0306 -1.3900 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5531 0.4537 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.3840 -0.5747 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.1878 0.4253 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.9199 0.4253 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.5232 -0.5458 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -8.3840 0.4253 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.5180 0.9253 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.9559 -1.0108 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.6519 0.4253 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.0539 0.9253 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0902 -0.0199 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5633 -0.8262 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 -3.1878 -0.5747 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.8964 -2.3810 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.3793 1.0171 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.2500 -1.0747 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.2500 0.9253 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.5180 1.9253 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.7470 -1.6225 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2991 0.5919 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.6245 0.2515 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.6519 -0.5747 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.7859 0.9253 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 44 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 29 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 1 0 0 0 24 31 1 0 0 0 0 24 35 1 6 0 0 0 25 31 1 0 0 0 0 25 45 1 6 0 0 0 26 33 1 6 0 0 0 27 28 1 0 0 0 0 27 39 1 6 0 0 0 28 30 1 0 0 0 0 28 40 1 1 0 0 0 29 32 1 0 0 0 0 29 41 1 1 0 0 0 30 44 1 0 0 0 0 30 45 1 6 0 0 0 32 42 1 0 0 0 0 33 34 1 6 0 0 0 34 7 1 1 0 0 0 35 43 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	634.37
Volume:	648.49
LogP:	2.202
LogD:	0.945
LogS:	-3.305
# Rotatable Bonds:	7
TPSA:	173.98
# H-Bond Aceptor:	10
# H-Bond Donor:	6
# Rings:	5
# Heavy Atoms:	10

MedChem Properties

QED Drug-Likeness Score:	0.244
Synthetic Accessibility Score:	5.894
Fsp3:	0.829
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:	-4.86
MDCK Permeability:	1.687997064436786e-05
Pgp-inhibitor:	0.998
Pgp-substrate:	0.972
Human Intestinal Absorption (HIA):	0.847
20% Bioavailability (F20%):	0.147
30% Bioavailability (F30%):	0.171

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.098
Plasma Protein Binding (PPB):	74.22050476074219%
Volume Distribution (VD):	0.486
Pgp-substrate:	11.472352027893066%

ADMET: Metabolism

CYP1A2-inhibitor:	0.001
CYP1A2-substrate:	0.084
CYP2C19-inhibitor:	0.005
CYP2C19-substrate:	0.531
CYP2C9-inhibitor:	0.01
CYP2C9-substrate:	0.082
CYP2D6-inhibitor:	0.003
CYP2D6-substrate:	0.111
CYP3A4-inhibitor:	0.026
CYP3A4-substrate:	0.17

ADMET: Excretion

Clearance (CL):	1.79
Half-life (T1/2):	0.718

ADMET: Toxicity

hERG Blockers:	0.043
Human Hepatotoxicity (H-HT):	0.307
Drug-inuced Liver Injury (DILI):	0.033
AMES Toxicity:	0.065
Rat Oral Acute Toxicity:	0.827
Maximum Recommended Daily Dose:	0.953
Skin Sensitization:	0.429
Carcinogencity:	0.167
Eye Corrosion:	0.003
Eye Irritation:	0.009
Respiratory Toxicity:	0.803

Download Data

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

Natural Product: NPC472076

Natural Product ID:	NPC472076
*Common Name:**	GZTBZPSVFLQPMS-PRZBVJLESA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	GZTBZPSVFLQPMS-PRZBVJLESA-N
Standard InCHI:	InChI=1S/C35H54O10/c1-18(14-21(36)29(41)32(4,5)42)26-22(37)16-34(7)20-8-9-24-31(2,3)25(45-30-28(40)27(39)23(38)17-44-30)11-13-35(24,43)15-19(20)10-12-33(26,34)6/h8,10,18,23-30,38-43H,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](C(O)(C)C)O)C)C)C2)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3337545
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[547072]
NPT165	Cell Line	HeLa	Homo sapiens	IC50	>	10000.0	nM	PMID[547072]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	10000.0	nM	PMID[547072]

☑ 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 NPC472076 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	247
0.1-0.2	1374
0.2-0.3	4703
0.3-0.4	9038
0.4-0.5	12571
0.5-0.6	7253
0.6-0.7	5549
0.7-0.8	1889
0.8-0.85	65
0.85-0.9	4
0.9-0.95	0
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC472075
0.9735	High Similarity	NPC472077
0.9735	High Similarity	NPC472078
0.885	High Similarity	NPC130427
0.8696	High Similarity	NPC474557
0.8696	High Similarity	NPC116024
0.8673	High Similarity	NPC154856
0.8673	High Similarity	NPC52241
0.8673	High Similarity	NPC475317
0.8644	High Similarity	NPC472257
0.8596	High Similarity	NPC292196
0.8522	High Similarity	NPC210420
0.8522	High Similarity	NPC474265
0.8487	Intermediate Similarity	NPC471406
0.8421	Intermediate Similarity	NPC265655
0.8376	Intermediate Similarity	NPC473882
0.8348	Intermediate Similarity	NPC129340
0.8333	Intermediate Similarity	NPC195708
0.8319	Intermediate Similarity	NPC210178
0.8319	Intermediate Similarity	NPC86020
0.8319	Intermediate Similarity	NPC475632
0.8305	Intermediate Similarity	NPC473126
0.8305	Intermediate Similarity	NPC279638
0.8291	Intermediate Similarity	NPC251309
0.8291	Intermediate Similarity	NPC260665
0.8276	Intermediate Similarity	NPC263827
0.8276	Intermediate Similarity	NPC250481
0.8276	Intermediate Similarity	NPC285410
0.8261	Intermediate Similarity	NPC477070
0.8261	Intermediate Similarity	NPC477069
0.8261	Intermediate Similarity	NPC218853
0.8261	Intermediate Similarity	NPC118225
0.822	Intermediate Similarity	NPC475163
0.822	Intermediate Similarity	NPC74727
0.822	Intermediate Similarity	NPC220293
0.8211	Intermediate Similarity	NPC130229
0.8205	Intermediate Similarity	NPC233003
0.819	Intermediate Similarity	NPC101450
0.819	Intermediate Similarity	NPC250956
0.8182	Intermediate Similarity	NPC475187
0.8174	Intermediate Similarity	NPC295389
0.8167	Intermediate Similarity	NPC473617
0.8167	Intermediate Similarity	NPC239293
0.8167	Intermediate Similarity	NPC473828
0.8158	Intermediate Similarity	NPC63023
0.8158	Intermediate Similarity	NPC95243
0.8158	Intermediate Similarity	NPC162033
0.8136	Intermediate Similarity	NPC200944
0.8136	Intermediate Similarity	NPC73455
0.812	Intermediate Similarity	NPC477073
0.812	Intermediate Similarity	NPC269466
0.8103	Intermediate Similarity	NPC246205
0.8087	Intermediate Similarity	NPC293512
0.807	Intermediate Similarity	NPC121566
0.807	Intermediate Similarity	NPC100955
0.807	Intermediate Similarity	NPC223741
0.8065	Intermediate Similarity	NPC475194
0.8065	Intermediate Similarity	NPC476674
0.8051	Intermediate Similarity	NPC174836
0.8049	Intermediate Similarity	NPC156789
0.8049	Intermediate Similarity	NPC216866
0.8034	Intermediate Similarity	NPC242611
0.8034	Intermediate Similarity	NPC90630
0.8034	Intermediate Similarity	NPC475243
0.8018	Intermediate Similarity	NPC472074
0.8018	Intermediate Similarity	NPC472073
0.8017	Intermediate Similarity	NPC258323
0.8017	Intermediate Similarity	NPC234522
0.8017	Intermediate Similarity	NPC45475
0.8	Intermediate Similarity	NPC174367
0.8	Intermediate Similarity	NPC31797
0.8	Intermediate Similarity	NPC244127
0.8	Intermediate Similarity	NPC476673
0.8	Intermediate Similarity	NPC475494
0.8	Intermediate Similarity	NPC47113
0.8	Intermediate Similarity	NPC198714
0.7984	Intermediate Similarity	NPC1980
0.7984	Intermediate Similarity	NPC141196
0.7984	Intermediate Similarity	NPC160084
0.7984	Intermediate Similarity	NPC238005
0.7984	Intermediate Similarity	NPC41129
0.7983	Intermediate Similarity	NPC75167
0.7983	Intermediate Similarity	NPC477074
0.7983	Intermediate Similarity	NPC477944
0.7983	Intermediate Similarity	NPC311592
0.7969	Intermediate Similarity	NPC473805
0.7969	Intermediate Similarity	NPC473519
0.7967	Intermediate Similarity	NPC476544
0.7967	Intermediate Similarity	NPC475182
0.7967	Intermediate Similarity	NPC476543
0.7967	Intermediate Similarity	NPC75417
0.7967	Intermediate Similarity	NPC202051
0.7967	Intermediate Similarity	NPC476545
0.7966	Intermediate Similarity	NPC31839
0.7966	Intermediate Similarity	NPC190837
0.7966	Intermediate Similarity	NPC272242
0.7953	Intermediate Similarity	NPC476966
0.7953	Intermediate Similarity	NPC471407
0.7951	Intermediate Similarity	NPC477071
0.7949	Intermediate Similarity	NPC8431
0.7949	Intermediate Similarity	NPC475364
0.792	Intermediate Similarity	NPC30188
0.792	Intermediate Similarity	NPC473474
0.792	Intermediate Similarity	NPC248202
0.792	Intermediate Similarity	NPC177820
0.7917	Intermediate Similarity	NPC181145
0.7917	Intermediate Similarity	NPC477580
0.7917	Intermediate Similarity	NPC165439
0.7913	Intermediate Similarity	NPC470885
0.7913	Intermediate Similarity	NPC221562
0.7913	Intermediate Similarity	NPC187400
0.7907	Intermediate Similarity	NPC102015
0.7903	Intermediate Similarity	NPC275343
0.7903	Intermediate Similarity	NPC28532
0.7899	Intermediate Similarity	NPC125923
0.7899	Intermediate Similarity	NPC65590
0.7899	Intermediate Similarity	NPC100383
0.7899	Intermediate Similarity	NPC80843
0.7899	Intermediate Similarity	NPC64106
0.7899	Intermediate Similarity	NPC243572
0.7899	Intermediate Similarity	NPC48249
0.7899	Intermediate Similarity	NPC37739
0.7899	Intermediate Similarity	NPC1046
0.7899	Intermediate Similarity	NPC212968
0.7899	Intermediate Similarity	NPC46388
0.7899	Intermediate Similarity	NPC161434
0.7899	Intermediate Similarity	NPC195132
0.7899	Intermediate Similarity	NPC470543
0.7895	Intermediate Similarity	NPC473788
0.7895	Intermediate Similarity	NPC136816
0.7895	Intermediate Similarity	NPC475558
0.7891	Intermediate Similarity	NPC173347
0.7886	Intermediate Similarity	NPC129393
0.7886	Intermediate Similarity	NPC476849
0.7881	Intermediate Similarity	NPC27551
0.7881	Intermediate Similarity	NPC114961
0.7881	Intermediate Similarity	NPC274507
0.7881	Intermediate Similarity	NPC470065
0.7879	Intermediate Similarity	NPC477232
0.7879	Intermediate Similarity	NPC477233
0.7874	Intermediate Similarity	NPC293623
0.7874	Intermediate Similarity	NPC188291
0.7874	Intermediate Similarity	NPC69273
0.7874	Intermediate Similarity	NPC311534
0.7874	Intermediate Similarity	NPC168899
0.7874	Intermediate Similarity	NPC245094
0.7869	Intermediate Similarity	NPC286347
0.7869	Intermediate Similarity	NPC188667
0.7869	Intermediate Similarity	NPC204552
0.7869	Intermediate Similarity	NPC297179
0.7863	Intermediate Similarity	NPC476123
0.7863	Intermediate Similarity	NPC28198
0.7863	Intermediate Similarity	NPC284807
0.7863	Intermediate Similarity	NPC177246
0.7857	Intermediate Similarity	NPC104427
0.7857	Intermediate Similarity	NPC181066
0.7857	Intermediate Similarity	NPC222307
0.7857	Intermediate Similarity	NPC469947
0.7846	Intermediate Similarity	NPC478069
0.7845	Intermediate Similarity	NPC473199
0.784	Intermediate Similarity	NPC476542
0.7833	Intermediate Similarity	NPC189884
0.7833	Intermediate Similarity	NPC269315
0.7833	Intermediate Similarity	NPC293038
0.7833	Intermediate Similarity	NPC238935
0.7833	Intermediate Similarity	NPC62696
0.7833	Intermediate Similarity	NPC178981
0.7833	Intermediate Similarity	NPC73986
0.7833	Intermediate Similarity	NPC47063
0.7833	Intermediate Similarity	NPC475208
0.7833	Intermediate Similarity	NPC204458
0.7833	Intermediate Similarity	NPC102619
0.7833	Intermediate Similarity	NPC271138
0.7833	Intermediate Similarity	NPC138334
0.7829	Intermediate Similarity	NPC231240
0.7829	Intermediate Similarity	NPC471855
0.7823	Intermediate Similarity	NPC476675
0.7823	Intermediate Similarity	NPC476672
0.7823	Intermediate Similarity	NPC42675
0.7823	Intermediate Similarity	NPC129434
0.7815	Intermediate Similarity	NPC471243
0.7815	Intermediate Similarity	NPC191763
0.7815	Intermediate Similarity	NPC211798
0.7815	Intermediate Similarity	NPC11035
0.7815	Intermediate Similarity	NPC297208
0.7815	Intermediate Similarity	NPC108748
0.7815	Intermediate Similarity	NPC235841
0.7815	Intermediate Similarity	NPC30397
0.7815	Intermediate Similarity	NPC473481
0.7815	Intermediate Similarity	NPC274833
0.7807	Intermediate Similarity	NPC88000
0.7807	Intermediate Similarity	NPC267510
0.7807	Intermediate Similarity	NPC472023
0.7807	Intermediate Similarity	NPC4831
0.7807	Intermediate Similarity	NPC160734
0.7807	Intermediate Similarity	NPC129372
0.7807	Intermediate Similarity	NPC309425
0.7807	Intermediate Similarity	NPC47566
0.7805	Intermediate Similarity	NPC475171
0.7805	Intermediate Similarity	NPC157868

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 NPC472076 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	215
0.1-0.2	1585
0.2-0.3	4009
0.3-0.4	2231
0.4-0.5	611
0.5-0.6	250
0.6-0.7	183
0.7-0.8	66
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
0.7903	Intermediate Similarity	NPD6370	Approved
0.7795	Intermediate Similarity	NPD8293	Discontinued
0.7778	Intermediate Similarity	NPD6412	Phase 2
0.7742	Intermediate Similarity	NPD6054	Approved
0.7742	Intermediate Similarity	NPD6059	Approved
0.7734	Intermediate Similarity	NPD7736	Approved
0.7698	Intermediate Similarity	NPD8328	Phase 3
0.7642	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.754	Intermediate Similarity	NPD6016	Approved
0.754	Intermediate Similarity	NPD6015	Approved
0.75	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7492	Approved
0.748	Intermediate Similarity	NPD5988	Approved
0.746	Intermediate Similarity	NPD6319	Approved
0.7459	Intermediate Similarity	NPD8297	Approved
0.7459	Intermediate Similarity	NPD6882	Approved
0.7442	Intermediate Similarity	NPD6616	Approved
0.7405	Intermediate Similarity	NPD7319	Approved
0.7385	Intermediate Similarity	NPD7078	Approved
0.7308	Intermediate Similarity	NPD7507	Approved
0.7266	Intermediate Similarity	NPD8516	Approved
0.7266	Intermediate Similarity	NPD8513	Phase 3
0.7266	Intermediate Similarity	NPD8515	Approved
0.7266	Intermediate Similarity	NPD8517	Approved
0.7258	Intermediate Similarity	NPD8133	Approved
0.725	Intermediate Similarity	NPD6675	Approved
0.725	Intermediate Similarity	NPD7128	Approved
0.725	Intermediate Similarity	NPD6402	Approved
0.725	Intermediate Similarity	NPD5739	Approved
0.7222	Intermediate Similarity	NPD6009	Approved
0.7213	Intermediate Similarity	NPD6372	Approved
0.7213	Intermediate Similarity	NPD6373	Approved
0.7197	Intermediate Similarity	NPD6033	Approved
0.7165	Intermediate Similarity	NPD7327	Approved
0.7165	Intermediate Similarity	NPD7328	Approved
0.7154	Intermediate Similarity	NPD4634	Approved
0.7132	Intermediate Similarity	NPD8033	Approved
0.7132	Intermediate Similarity	NPD7503	Approved
0.7131	Intermediate Similarity	NPD6686	Approved
0.7131	Intermediate Similarity	NPD7320	Approved
0.7131	Intermediate Similarity	NPD6899	Approved
0.7131	Intermediate Similarity	NPD6881	Approved
0.712	Intermediate Similarity	NPD4632	Approved
0.7109	Intermediate Similarity	NPD7516	Approved
0.7097	Intermediate Similarity	NPD6650	Approved
0.7097	Intermediate Similarity	NPD8130	Phase 1
0.7097	Intermediate Similarity	NPD6649	Approved
0.7094	Intermediate Similarity	NPD4755	Approved
0.7087	Intermediate Similarity	NPD7115	Discovery
0.7054	Intermediate Similarity	NPD8294	Approved
0.7054	Intermediate Similarity	NPD8377	Approved
0.7049	Intermediate Similarity	NPD5701	Approved
0.7049	Intermediate Similarity	NPD5697	Approved
0.7043	Intermediate Similarity	NPD6399	Phase 3
0.7016	Intermediate Similarity	NPD7290	Approved
0.7016	Intermediate Similarity	NPD7102	Approved
0.7016	Intermediate Similarity	NPD6883	Approved
0.7	Intermediate Similarity	NPD8296	Approved
0.7	Intermediate Similarity	NPD8378	Approved
0.7	Intermediate Similarity	NPD8335	Approved
0.7	Intermediate Similarity	NPD8380	Approved
0.7	Intermediate Similarity	NPD8379	Approved
0.6992	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD5286	Approved
0.6975	Remote Similarity	NPD4700	Approved
0.6975	Remote Similarity	NPD4696	Approved
0.6975	Remote Similarity	NPD5285	Approved
0.696	Remote Similarity	NPD6617	Approved
0.696	Remote Similarity	NPD6869	Approved
0.696	Remote Similarity	NPD6847	Approved
0.6949	Remote Similarity	NPD6084	Phase 2
0.6949	Remote Similarity	NPD6083	Phase 2
0.6937	Remote Similarity	NPD4786	Approved
0.6935	Remote Similarity	NPD6012	Approved
0.6935	Remote Similarity	NPD6013	Approved
0.6935	Remote Similarity	NPD6014	Approved
0.6894	Remote Similarity	NPD6067	Discontinued
0.6891	Remote Similarity	NPD5696	Approved
0.686	Remote Similarity	NPD5225	Approved
0.686	Remote Similarity	NPD4633	Approved
0.686	Remote Similarity	NPD5226	Approved
0.686	Remote Similarity	NPD5224	Approved
0.686	Remote Similarity	NPD5211	Phase 2
0.6855	Remote Similarity	NPD6011	Approved
0.6829	Remote Similarity	NPD4768	Approved
0.6829	Remote Similarity	NPD4767	Approved
0.6825	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6814	Remote Similarity	NPD5279	Phase 3
0.681	Remote Similarity	NPD6411	Approved
0.6803	Remote Similarity	NPD5175	Approved
0.6803	Remote Similarity	NPD5174	Approved
0.6783	Remote Similarity	NPD4753	Phase 2
0.6783	Remote Similarity	NPD5328	Approved
0.678	Remote Similarity	NPD5210	Approved
0.678	Remote Similarity	NPD5695	Phase 3
0.678	Remote Similarity	NPD4629	Approved
0.6777	Remote Similarity	NPD5223	Approved
0.6767	Remote Similarity	NPD7604	Phase 2
0.6757	Remote Similarity	NPD3667	Approved
0.6752	Remote Similarity	NPD4202	Approved
0.6748	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6748	Remote Similarity	NPD5141	Approved
0.6742	Remote Similarity	NPD5983	Phase 2
0.6741	Remote Similarity	NPD8074	Phase 3
0.6723	Remote Similarity	NPD5221	Approved
0.6723	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6723	Remote Similarity	NPD5222	Approved
0.6723	Remote Similarity	NPD4697	Phase 3
0.672	Remote Similarity	NPD4730	Approved
0.672	Remote Similarity	NPD4729	Approved
0.6715	Remote Similarity	NPD5956	Approved
0.6667	Remote Similarity	NPD4754	Approved
0.6667	Remote Similarity	NPD5173	Approved
0.6667	Remote Similarity	NPD6336	Discontinued
0.6667	Remote Similarity	NPD3618	Phase 1
0.6667	Remote Similarity	NPD6079	Approved
0.6638	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6638	Remote Similarity	NPD6101	Approved
0.6619	Remote Similarity	NPD8338	Approved
0.6615	Remote Similarity	NPD6274	Approved
0.6614	Remote Similarity	NPD5249	Phase 3
0.6614	Remote Similarity	NPD5247	Approved
0.6614	Remote Similarity	NPD5251	Approved
0.6614	Remote Similarity	NPD5250	Approved
0.6614	Remote Similarity	NPD5248	Approved
0.6591	Remote Similarity	NPD7100	Approved
0.6591	Remote Similarity	NPD7101	Approved
0.6587	Remote Similarity	NPD5128	Approved
0.6569	Remote Similarity	NPD8337	Approved
0.6569	Remote Similarity	NPD8336	Approved
0.6562	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.656	Remote Similarity	NPD6008	Approved
0.6555	Remote Similarity	NPD7748	Approved
0.6552	Remote Similarity	NPD6672	Approved
0.6552	Remote Similarity	NPD5737	Approved
0.6547	Remote Similarity	NPD7260	Phase 2
0.6535	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6529	Remote Similarity	NPD7902	Approved
0.6525	Remote Similarity	NPD6050	Approved
0.6525	Remote Similarity	NPD8035	Phase 2
0.6525	Remote Similarity	NPD8034	Phase 2
0.6522	Remote Similarity	NPD5280	Approved
0.6522	Remote Similarity	NPD4694	Approved
0.6515	Remote Similarity	NPD6335	Approved
0.6493	Remote Similarity	NPD6909	Approved
0.6493	Remote Similarity	NPD6921	Approved
0.6493	Remote Similarity	NPD6908	Approved
0.6475	Remote Similarity	NPD7638	Approved
0.6466	Remote Similarity	NPD7524	Approved
0.6441	Remote Similarity	NPD5692	Phase 3
0.6439	Remote Similarity	NPD6317	Approved
0.6435	Remote Similarity	NPD5329	Approved
0.6434	Remote Similarity	NPD5215	Approved
0.6434	Remote Similarity	NPD5216	Approved
0.6434	Remote Similarity	NPD5217	Approved
0.6429	Remote Similarity	NPD7525	Registered
0.6423	Remote Similarity	NPD7639	Approved
0.6423	Remote Similarity	NPD7640	Approved
0.6417	Remote Similarity	NPD5282	Discontinued
0.6391	Remote Similarity	NPD6313	Approved
0.6391	Remote Similarity	NPD6314	Approved
0.6387	Remote Similarity	NPD5284	Approved
0.6387	Remote Similarity	NPD7515	Phase 2
0.6387	Remote Similarity	NPD5281	Approved
0.6387	Remote Similarity	NPD7637	Suspended
0.6387	Remote Similarity	NPD7983	Approved
0.6387	Remote Similarity	NPD5694	Approved
0.6379	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6379	Remote Similarity	NPD6098	Approved
0.6378	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD6868	Approved
0.6357	Remote Similarity	NPD5135	Approved
0.6357	Remote Similarity	NPD5169	Approved
0.6357	Remote Similarity	NPD6371	Approved
0.6357	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6357	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6356	Remote Similarity	NPD6673	Approved
0.6356	Remote Similarity	NPD6080	Approved
0.6356	Remote Similarity	NPD6904	Approved
0.6348	Remote Similarity	NPD3133	Approved
0.6348	Remote Similarity	NPD3666	Approved
0.6348	Remote Similarity	NPD3668	Phase 3
0.6348	Remote Similarity	NPD4197	Approved
0.6348	Remote Similarity	NPD3665	Phase 1
0.6348	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6343	Remote Similarity	NPD4522	Approved
0.6341	Remote Similarity	NPD4225	Approved
0.6333	Remote Similarity	NPD5779	Approved
0.6333	Remote Similarity	NPD5778	Approved
0.6308	Remote Similarity	NPD5127	Approved
0.6293	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6281	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6281	Remote Similarity	NPD7900	Approved
0.628	Remote Similarity	NPD7799	Discontinued
0.6268	Remote Similarity	NPD6845	Suspended
0.6261	Remote Similarity	NPD6695	Phase 3
0.626	Remote Similarity	NPD6053	Discontinued
0.625	Remote Similarity	NPD8274	Clinical (unspecified phase)
0.625	Remote Similarity	NPD8444	Approved
0.625	Remote Similarity	NPD6291	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