NPASS Compound

Structure

NPC114700 OpenBabel07101719252D 50 57 0 0 1 0 0 0 0 0999 V2000 1.7175 -2.7929 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.2212 -0.9440 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5137 0.1712 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2571 -3.0779 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7571 -3.9440 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4889 2.2603 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0988 1.4513 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1609 -3.2530 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2875 -1.8394 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8910 -2.4440 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0250 -1.9440 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8910 -5.4440 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0250 -4.9440 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4269 -3.4440 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2930 -3.9440 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8985 -1.0703 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.2212 -4.9440 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1590 -4.4440 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3107 -1.8794 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -8.2212 -1.9440 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6182 1.1657 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.2212 -3.9440 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.4918 -0.1568 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.8910 -3.4440 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.1590 -2.4440 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.7571 -4.9440 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.4891 -3.9440 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -7.3551 -3.4440 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.3162 -1.7748 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.7912 0.3522 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.4891 -4.9440 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.0850 -0.9658 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.7571 -3.9440 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8957 1.3468 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4269 -2.4440 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.2930 -1.9440 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.0250 -3.9440 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.1590 -3.4440 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0905 -0.8613 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -9.0872 -2.4440 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.5318 1.5725 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.0872 -3.4440 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.6231 -3.4440 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7542 -0.2227 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.3551 -5.4440 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.3551 -2.4440 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.6231 -5.4440 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.8092 1.7535 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.4973 -0.0523 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 20 1 0 0 0 0 3 21 1 0 0 0 0 4 33 1 0 0 0 0 5 33 1 0 0 0 0 6 34 1 0 0 0 0 7 34 1 0 0 0 0 8 35 1 0 0 0 0 10 11 1 0 0 0 0 10 24 1 0 0 0 0 11 25 1 0 0 0 0 12 13 1 0 0 0 0 12 26 1 0 0 0 0 13 37 1 0 0 0 0 14 15 1 0 0 0 0 14 35 1 0 0 0 0 16 19 1 0 0 0 0 17 22 1 0 0 0 0 17 45 1 0 0 0 0 18 37 1 0 0 0 0 18 38 1 0 0 0 0 19 1 1 1 0 0 0 19 29 1 0 0 0 0 20 40 2 0 0 0 0 20 46 1 0 0 0 0 21 41 2 0 0 0 0 21 48 1 0 0 0 0 22 28 1 0 0 0 0 22 42 1 1 0 0 0 23 16 1 1 0 0 0 23 30 1 0 0 0 0 23 49 1 0 0 0 0 24 33 1 0 0 0 0 24 37 1 6 0 0 0 25 36 1 1 0 0 0 25 38 1 0 0 0 0 26 33 1 0 0 0 0 26 47 1 6 0 0 0 27 28 1 0 0 0 0 27 31 1 0 0 0 0 27 43 1 1 0 0 0 28 46 1 6 0 0 0 29 35 1 6 0 0 0 29 39 1 0 0 0 0 30 34 1 6 0 0 0 30 50 1 0 0 0 0 31 45 1 0 0 0 0 31 47 1 6 0 0 0 32 36 1 1 0 0 0 32 39 1 0 0 0 0 32 44 1 0 0 0 0 34 48 1 0 0 0 0 35 36 1 6 0 0 0 36 9 1 1 0 0 0 37 38 1 1 0 0 0 38 15 1 1 0 0 0 39 49 1 6 0 0 0 39 50 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	704.41
Volume:	706.068
LogP:	4.802
LogD:	3.712
LogS:	-4.246
# Rotatable Bonds:	7
TPSA:	150.21
# H-Bond Aceptor:	11
# H-Bond Donor:	3
# Rings:	8
# Heavy Atoms:	11

MedChem Properties

QED Drug-Likeness Score:	0.278
Synthetic Accessibility Score:	7.456
Fsp3:	0.949
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:	-5.361
MDCK Permeability:	5.198676444706507e-05
Pgp-inhibitor:	0.995
Pgp-substrate:	0.564
Human Intestinal Absorption (HIA):	0.009
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.571

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.006
Plasma Protein Binding (PPB):	83.8615951538086%
Volume Distribution (VD):	0.986
Pgp-substrate:	8.448071479797363%

ADMET: Metabolism

CYP1A2-inhibitor:	0.001
CYP1A2-substrate:	0.487
CYP2C19-inhibitor:	0.005
CYP2C19-substrate:	0.448
CYP2C9-inhibitor:	0.055
CYP2C9-substrate:	0.008
CYP2D6-inhibitor:	0.036
CYP2D6-substrate:	0.128
CYP3A4-inhibitor:	0.526
CYP3A4-substrate:	0.282

ADMET: Excretion

Clearance (CL):	1.547
Half-life (T1/2):	0.325

ADMET: Toxicity

hERG Blockers:	0.786
Human Hepatotoxicity (H-HT):	0.943
Drug-inuced Liver Injury (DILI):	0.262
AMES Toxicity:	0.009
Rat Oral Acute Toxicity:	0.333
Maximum Recommended Daily Dose:	0.889
Skin Sensitization:	0.412
Carcinogencity:	0.016
Eye Corrosion:	0.003
Eye Irritation:	0.014
Respiratory Toxicity:	0.983

Download Data

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

Natural Product: NPC114700

Natural Product ID:	NPC114700
*Common Name:**	RQEFTCPCSKWKPF-SQLYFSCNSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	RQEFTCPCSKWKPF-SQLYFSCNSA-N
Standard InCHI:	InChI=1S/C39H60O11/c1-19-16-23-30(34(6,7)48-21(3)41)50-39(49-23)29(19)35(8)14-15-38-18-37(38)13-12-26(47-31-27(43)28(46-20(2)40)22(42)17-45-31)33(4,5)24(37)10-11-25(38)36(35,9)32(39)44/h19,22-32,42-44H,10-18H2,1-9H3/t19-,22-,23-,24+,25+,26+,27-,28+,29-,30+,31+,32-,35-,36-,37-,38+,39+/m1/s1
SMILES:	C[C@@H]1C[C@@H]2[C@@H](C(C)(C)OC(=O)C)O[C@]3([C@H]1[C@@]1(C)CC[C@]45C[C@]65CC[C@@H](C(C)(C)[C@@H]6CC[C@H]4[C@]1(C)[C@H]3O)O[C@H]1[C@@H]([C@H]([C@@H](CO1)O)OC(=O)C)O)O2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3337553
PubChem CID:	46184085
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001013] Steroidal glycosides [CHEMONTID:0002364] Steroidal saponins [CHEMONTID:0001687] Cucurbitacin glycosides

*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[448468]
NPT165	Cell Line	HeLa	Homo sapiens	IC50	>	10000.0	nM	PMID[448468]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	5500.0	nM	PMID[448468]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	10000.0	nM	PMID[448468]

☑ 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 NPC114700 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	574
0.1-0.2	4857
0.2-0.3	13870
0.3-0.4	10098
0.4-0.5	5843
0.5-0.6	3825
0.6-0.7	2159
0.7-0.8	1135
0.8-0.85	131
0.85-0.9	140
0.9-0.95	41
0.95-1	24

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC310138
1.0	High Similarity	NPC134967
1.0	High Similarity	NPC470029
0.9894	High Similarity	NPC472081
0.9894	High Similarity	NPC476512
0.9894	High Similarity	NPC108227
0.9688	High Similarity	NPC476837
0.9688	High Similarity	NPC139181
0.9688	High Similarity	NPC97260
0.9684	High Similarity	NPC476838
0.9684	High Similarity	NPC476839
0.9574	High Similarity	NPC233649
0.9574	High Similarity	NPC470028
0.9479	High Similarity	NPC475574
0.9468	High Similarity	NPC238796
0.9468	High Similarity	NPC142264
0.9468	High Similarity	NPC237071
0.9468	High Similarity	NPC203434
0.9468	High Similarity	NPC476510
0.9468	High Similarity	NPC156377
0.9375	High Similarity	NPC470030
0.9362	High Similarity	NPC473065
0.9362	High Similarity	NPC473067
0.9362	High Similarity	NPC473064
0.9263	High Similarity	NPC296936
0.9255	High Similarity	NPC191915
0.9255	High Similarity	NPC252253
0.9255	High Similarity	NPC151214
0.9255	High Similarity	NPC45959
0.9255	High Similarity	NPC175
0.9167	High Similarity	NPC470591
0.9167	High Similarity	NPC475207
0.9167	High Similarity	NPC210157
0.9158	High Similarity	NPC474399
0.9158	High Similarity	NPC94582
0.9158	High Similarity	NPC57964
0.9149	High Similarity	NPC144790
0.9149	High Similarity	NPC88962
0.9149	High Similarity	NPC149400
0.9149	High Similarity	NPC473726
0.9062	High Similarity	NPC139271
0.9062	High Similarity	NPC252056
0.9062	High Similarity	NPC304011
0.9053	High Similarity	NPC309866
0.9053	High Similarity	NPC131693
0.9053	High Similarity	NPC291547
0.9053	High Similarity	NPC174024
0.9053	High Similarity	NPC312678
0.9053	High Similarity	NPC24960
0.9053	High Similarity	NPC253268
0.9053	High Similarity	NPC475436
0.9053	High Similarity	NPC473774
0.9053	High Similarity	NPC473851
0.9053	High Similarity	NPC179859
0.9043	High Similarity	NPC307167
0.9043	High Similarity	NPC229801
0.9043	High Similarity	NPC210759
0.9043	High Similarity	NPC473066
0.8969	High Similarity	NPC274200
0.8969	High Similarity	NPC477223
0.8969	High Similarity	NPC477222
0.8958	High Similarity	NPC92196
0.8947	High Similarity	NPC177834
0.8947	High Similarity	NPC141769
0.8947	High Similarity	NPC167644
0.8947	High Similarity	NPC477451
0.8947	High Similarity	NPC325828
0.8947	High Similarity	NPC250393
0.8947	High Similarity	NPC48339
0.8947	High Similarity	NPC297348
0.8947	High Similarity	NPC311246
0.8947	High Similarity	NPC249204
0.8947	High Similarity	NPC477547
0.8947	High Similarity	NPC234352
0.8936	High Similarity	NPC473542
0.8936	High Similarity	NPC65550
0.8866	High Similarity	NPC121453
0.8854	High Similarity	NPC305418
0.8854	High Similarity	NPC3538
0.8854	High Similarity	NPC217205
0.8854	High Similarity	NPC471464
0.8854	High Similarity	NPC264101
0.8854	High Similarity	NPC113500
0.8854	High Similarity	NPC294686
0.8854	High Similarity	NPC222731
0.8854	High Similarity	NPC291203
0.8854	High Similarity	NPC30687
0.8854	High Similarity	NPC477224
0.8842	High Similarity	NPC204881
0.8842	High Similarity	NPC36372
0.8842	High Similarity	NPC5632
0.8842	High Similarity	NPC59006
0.8842	High Similarity	NPC149966
0.8842	High Similarity	NPC473830
0.883	High Similarity	NPC228059
0.883	High Similarity	NPC102725
0.883	High Similarity	NPC131466
0.883	High Similarity	NPC82955
0.8776	High Similarity	NPC307534
0.8776	High Similarity	NPC476112
0.8763	High Similarity	NPC107962
0.8763	High Similarity	NPC6295
0.8763	High Similarity	NPC473727
0.8763	High Similarity	NPC19400
0.8763	High Similarity	NPC475351
0.8763	High Similarity	NPC107188
0.8763	High Similarity	NPC473610
0.8763	High Similarity	NPC211354
0.8763	High Similarity	NPC206003
0.875	High Similarity	NPC277774
0.875	High Similarity	NPC172838
0.875	High Similarity	NPC137004
0.8738	High Similarity	NPC472079
0.8737	High Similarity	NPC279329
0.8737	High Similarity	NPC223143
0.8723	High Similarity	NPC281004
0.8687	High Similarity	NPC292775
0.8687	High Similarity	NPC473616
0.8687	High Similarity	NPC473518
0.8687	High Similarity	NPC291548
0.8673	High Similarity	NPC470864
0.8673	High Similarity	NPC84111
0.8673	High Similarity	NPC470866
0.8673	High Similarity	NPC160426
0.8673	High Similarity	NPC473601
0.8673	High Similarity	NPC132080
0.8673	High Similarity	NPC30856
0.8673	High Similarity	NPC287483
0.8673	High Similarity	NPC475625
0.8673	High Similarity	NPC103616
0.8673	High Similarity	NPC98018
0.8673	High Similarity	NPC475643
0.8673	High Similarity	NPC284104
0.8673	High Similarity	NPC116756
0.8673	High Similarity	NPC128572
0.8673	High Similarity	NPC232037
0.8673	High Similarity	NPC470865
0.8673	High Similarity	NPC97700
0.8673	High Similarity	NPC195297
0.8673	High Similarity	NPC470863
0.8673	High Similarity	NPC184617
0.8646	High Similarity	NPC293609
0.8632	High Similarity	NPC20822
0.8632	High Similarity	NPC473472
0.8617	High Similarity	NPC140446
0.8617	High Similarity	NPC43912
0.86	High Similarity	NPC41843
0.8586	High Similarity	NPC470862
0.8586	High Similarity	NPC51520
0.8586	High Similarity	NPC83137
0.8586	High Similarity	NPC303069
0.8586	High Similarity	NPC232611
0.8586	High Similarity	NPC470861
0.8586	High Similarity	NPC115165
0.8571	High Similarity	NPC21897
0.8557	High Similarity	NPC122083
0.8557	High Similarity	NPC211845
0.8557	High Similarity	NPC182740
0.8557	High Similarity	NPC256104
0.8519	High Similarity	NPC212660
0.8515	High Similarity	NPC477172
0.85	High Similarity	NPC209798
0.85	High Similarity	NPC471374
0.85	High Similarity	NPC473638
0.85	High Similarity	NPC471375
0.8485	Intermediate Similarity	NPC473287
0.8469	Intermediate Similarity	NPC473503
0.8469	Intermediate Similarity	NPC475325
0.8454	Intermediate Similarity	NPC476668
0.8454	Intermediate Similarity	NPC473637
0.8416	Intermediate Similarity	NPC471426
0.8416	Intermediate Similarity	NPC471428
0.8416	Intermediate Similarity	NPC20028
0.8416	Intermediate Similarity	NPC51579
0.8416	Intermediate Similarity	NPC471427
0.8411	Intermediate Similarity	NPC477489
0.8404	Intermediate Similarity	NPC290612
0.8384	Intermediate Similarity	NPC477494
0.8384	Intermediate Similarity	NPC215570
0.8384	Intermediate Similarity	NPC469710
0.8367	Intermediate Similarity	NPC476669
0.8365	Intermediate Similarity	NPC215408
0.8333	Intermediate Similarity	NPC477225
0.8318	Intermediate Similarity	NPC473062
0.8318	Intermediate Similarity	NPC469824
0.8316	Intermediate Similarity	NPC471411
0.8316	Intermediate Similarity	NPC471410
0.8316	Intermediate Similarity	NPC155531
0.8316	Intermediate Similarity	NPC215968
0.8316	Intermediate Similarity	NPC477283
0.8302	Intermediate Similarity	NPC208333
0.8302	Intermediate Similarity	NPC476835
0.8302	Intermediate Similarity	NPC227879
0.8298	Intermediate Similarity	NPC474156
0.8286	Intermediate Similarity	NPC203974
0.8273	Intermediate Similarity	NPC179429
0.8269	Intermediate Similarity	NPC469827
0.8257	Intermediate Similarity	NPC79193
0.8252	Intermediate Similarity	NPC80191
0.8252	Intermediate Similarity	NPC310031

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 NPC114700 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	577
0.1-0.2	4473
0.2-0.3	2884
0.3-0.4	653
0.4-0.5	341
0.5-0.6	164
0.6-0.7	43
0.7-0.8	13
0.8-0.85	0
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8947	High Similarity	NPD8171	Discontinued
0.8447	Intermediate Similarity	NPD8170	Clinical (unspecified phase)
0.7895	Intermediate Similarity	NPD8294	Approved
0.7895	Intermediate Similarity	NPD8377	Approved
0.7872	Intermediate Similarity	NPD6928	Phase 2
0.7826	Intermediate Similarity	NPD8378	Approved
0.7826	Intermediate Similarity	NPD8296	Approved
0.7826	Intermediate Similarity	NPD8380	Approved
0.7826	Intermediate Similarity	NPD8335	Approved
0.7826	Intermediate Similarity	NPD8033	Approved
0.7826	Intermediate Similarity	NPD8379	Approved
0.7679	Intermediate Similarity	NPD8133	Approved
0.7565	Intermediate Similarity	NPD7327	Approved
0.7565	Intermediate Similarity	NPD7328	Approved
0.75	Intermediate Similarity	NPD7516	Approved
0.7131	Intermediate Similarity	NPD7507	Approved
0.7083	Intermediate Similarity	NPD7503	Approved
0.7018	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7016	Intermediate Similarity	NPD7736	Approved
0.7009	Intermediate Similarity	NPD7991	Discontinued
0.696	Remote Similarity	NPD7319	Approved
0.6931	Remote Similarity	NPD3669	Approved
0.6931	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.6891	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6809	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.6807	Remote Similarity	NPD6940	Discontinued
0.68	Remote Similarity	NPD8293	Discontinued
0.6768	Remote Similarity	NPD6118	Approved
0.6768	Remote Similarity	NPD6114	Approved
0.6768	Remote Similarity	NPD6697	Approved
0.6768	Remote Similarity	NPD6115	Approved
0.6701	Remote Similarity	NPD1810	Approved
0.6701	Remote Similarity	NPD1811	Approved
0.6696	Remote Similarity	NPD6412	Phase 2
0.6667	Remote Similarity	NPD6116	Phase 1
0.6613	Remote Similarity	NPD6370	Approved
0.6566	Remote Similarity	NPD6117	Approved
0.656	Remote Similarity	NPD8328	Phase 3
0.6508	Remote Similarity	NPD7492	Approved
0.6457	Remote Similarity	NPD6616	Approved
0.6452	Remote Similarity	NPD6059	Approved
0.6452	Remote Similarity	NPD6054	Approved
0.6406	Remote Similarity	NPD7078	Approved
0.6404	Remote Similarity	NPD1700	Approved
0.6392	Remote Similarity	NPD2686	Approved
0.6392	Remote Similarity	NPD7532	Clinical (unspecified phase)
0.6392	Remote Similarity	NPD2687	Approved
0.6392	Remote Similarity	NPD2254	Approved
0.6379	Remote Similarity	NPD4056	Clinical (unspecified phase)
0.6379	Remote Similarity	NPD4057	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.63	Remote Similarity	NPD3702	Approved
0.6288	Remote Similarity	NPD8449	Approved
0.6286	Remote Similarity	NPD7625	Phase 1
0.6273	Remote Similarity	NPD8034	Phase 2
0.6273	Remote Similarity	NPD8035	Phase 2
0.627	Remote Similarity	NPD6016	Approved
0.627	Remote Similarity	NPD6015	Approved
0.625	Remote Similarity	NPD1780	Approved
0.625	Remote Similarity	NPD1779	Approved
0.6241	Remote Similarity	NPD8450	Suspended
0.6224	Remote Similarity	NPD4787	Phase 1
0.622	Remote Similarity	NPD5988	Approved
0.6218	Remote Similarity	NPD6686	Approved
0.6218	Remote Similarity	NPD8174	Phase 2
0.619	Remote Similarity	NPD6319	Approved
0.6172	Remote Similarity	NPD6067	Discontinued
0.6148	Remote Similarity	NPD8297	Approved
0.6148	Remote Similarity	NPD6882	Approved
0.6087	Remote Similarity	NPD7638	Approved
0.608	Remote Similarity	NPD6009	Approved
0.6034	Remote Similarity	NPD7640	Approved
0.6034	Remote Similarity	NPD7639	Approved
0.6019	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6016	Remote Similarity	NPD8517	Approved
0.6016	Remote Similarity	NPD8513	Phase 3
0.6016	Remote Similarity	NPD8515	Approved
0.6016	Remote Similarity	NPD8516	Approved
0.6	Remote Similarity	NPD5777	Approved
0.6	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.5985	Remote Similarity	NPD6033	Approved
0.598	Remote Similarity	NPD3703	Phase 2
0.5968	Remote Similarity	NPD4632	Approved
0.595	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.595	Remote Similarity	NPD7320	Approved
0.5938	Remote Similarity	NPD371	Approved
0.5932	Remote Similarity	NPD7632	Discontinued
0.5923	Remote Similarity	NPD7604	Phase 2
0.5917	Remote Similarity	NPD6402	Approved
0.5917	Remote Similarity	NPD6008	Approved
0.5917	Remote Similarity	NPD6675	Approved
0.5917	Remote Similarity	NPD5739	Approved
0.5917	Remote Similarity	NPD7128	Approved
0.5902	Remote Similarity	NPD6372	Approved
0.5902	Remote Similarity	NPD6373	Approved
0.5902	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.59	Remote Similarity	NPD4244	Approved
0.59	Remote Similarity	NPD4245	Approved
0.5868	Remote Similarity	NPD7646	Clinical (unspecified phase)
0.5849	Remote Similarity	NPD7525	Registered
0.582	Remote Similarity	NPD6899	Approved
0.582	Remote Similarity	NPD6881	Approved
0.5806	Remote Similarity	NPD8130	Phase 1
0.5806	Remote Similarity	NPD6649	Approved
0.5806	Remote Similarity	NPD6650	Approved
0.58	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.58	Remote Similarity	NPD3698	Phase 2
0.58	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.5763	Remote Similarity	NPD8418	Phase 2
0.5738	Remote Similarity	NPD5697	Approved
0.5738	Remote Similarity	NPD5701	Approved
0.5726	Remote Similarity	NPD7102	Approved
0.5726	Remote Similarity	NPD7290	Approved
0.5726	Remote Similarity	NPD6883	Approved
0.5726	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.5703	Remote Similarity	NPD7115	Discovery
0.57	Remote Similarity	NPD5360	Phase 3
0.57	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.569	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.5686	Remote Similarity	NPD6081	Approved
0.568	Remote Similarity	NPD6869	Approved
0.568	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.568	Remote Similarity	NPD6617	Approved
0.568	Remote Similarity	NPD6847	Approved
0.5667	Remote Similarity	NPD8085	Approved
0.5667	Remote Similarity	NPD8139	Approved
0.5667	Remote Similarity	NPD8138	Approved
0.5667	Remote Similarity	NPD8084	Approved
0.5667	Remote Similarity	NPD8083	Approved
0.5667	Remote Similarity	NPD8086	Approved
0.5667	Remote Similarity	NPD8082	Approved
0.5649	Remote Similarity	NPD5983	Phase 2
0.5645	Remote Similarity	NPD6014	Approved
0.5645	Remote Similarity	NPD6012	Approved
0.5645	Remote Similarity	NPD6013	Approved
0.5625	Remote Similarity	NPD7755	Approved
0.5625	Remote Similarity	NPD7754	Approved
0.562	Remote Similarity	NPD7912	Approved
0.562	Remote Similarity	NPD8275	Approved
0.562	Remote Similarity	NPD7986	Approved
0.562	Remote Similarity	NPD8276	Approved
0.562	Remote Similarity	NPD7987	Approved
0.562	Remote Similarity	NPD7911	Approved
0.5603	Remote Similarity	NPD7748	Approved
0.56	Remote Similarity	NPD4634	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