NPASS Compound

Structure

NPC472933 OpenBabel07101718312D 51 54 0 0 1 0 0 0 0 0999 V2000 0.5909 -3.0032 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1653 -5.3212 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8301 6.8301 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9641 2.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4067 -1.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4067 0.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5472 -3.4190 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2382 -2.4680 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8781 -4.1622 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5388 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 7.1962 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 5.4641 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9641 2.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2601 -2.2601 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.1871 -5.1132 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 -1.3090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.3301 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9641 8.0622 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9641 4.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.5180 -5.8564 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9641 6.3301 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5981 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.4641 2.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 C 0 0 2 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 -1.7321 -4.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.2601 1.2601 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 8.9282 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.9641 8.0622 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.9641 4.5981 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.8270 -6.8074 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.5398 -5.6485 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.8301 5.8301 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 3.7321 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -2.5000 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 7 37 1 0 0 0 0 9 10 1 0 0 0 0 9 11 1 0 0 0 0 10 19 1 0 0 0 0 11 20 2 0 0 0 0 12 13 1 0 0 0 0 12 25 1 0 0 0 0 13 35 1 0 0 0 0 14 22 1 0 0 0 0 14 26 1 0 0 0 0 15 23 1 0 0 0 0 15 24 1 0 0 0 0 16 27 1 0 0 0 0 16 34 1 0 0 0 0 17 28 1 0 0 0 0 17 34 1 0 0 0 0 18 36 1 0 0 0 0 18 50 1 0 0 0 0 19 1 1 1 0 0 0 19 22 1 0 0 0 0 20 33 1 0 0 0 0 21 39 2 0 0 0 0 21 51 1 0 0 0 0 22 37 1 6 0 0 0 23 29 1 0 0 0 0 23 40 1 6 0 0 0 24 35 1 6 0 0 0 24 36 1 0 0 0 0 25 36 1 0 0 0 0 25 41 2 0 0 0 0 26 38 1 0 0 0 0 26 42 2 0 0 0 0 27 43 2 0 0 0 0 27 44 1 0 0 0 0 28 45 2 0 0 0 0 28 50 1 0 0 0 0 29 30 2 0 0 0 0 29 38 1 0 0 0 0 30 31 1 0 0 0 0 30 35 1 0 0 0 0 31 32 1 0 0 0 0 31 46 2 0 0 0 0 32 37 1 1 0 0 0 32 51 1 0 0 0 0 33 47 2 0 0 0 0 33 48 1 0 0 0 0 34 4 1 6 0 0 0 34 49 1 0 0 0 0 35 5 1 6 0 0 0 36 6 1 6 0 0 0 37 38 1 6 0 0 0 38 8 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	716.34
Volume:	722.123
LogP:	2.443
LogD:	1.022
LogS:	-3.061
# Rotatable Bonds:	14
TPSA:	215.71
# H-Bond Aceptor:	13
# H-Bond Donor:	3
# Rings:	4
# Heavy Atoms:	13

MedChem Properties

QED Drug-Likeness Score:	0.193
Synthetic Accessibility Score:	5.758
Fsp3:	0.737
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:	-5.658
MDCK Permeability:	2.4682780349394307e-05
Pgp-inhibitor:	0.054
Pgp-substrate:	0.471
Human Intestinal Absorption (HIA):	0.431
20% Bioavailability (F20%):	0.901
30% Bioavailability (F30%):	0.924

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.09
Plasma Protein Binding (PPB):	69.13127899169922%
Volume Distribution (VD):	0.457
Pgp-substrate:	15.182474136352539%

ADMET: Metabolism

CYP1A2-inhibitor:	0.0
CYP1A2-substrate:	0.122
CYP2C19-inhibitor:	0.007
CYP2C19-substrate:	0.09
CYP2C9-inhibitor:	0.019
CYP2C9-substrate:	0.419
CYP2D6-inhibitor:	0.01
CYP2D6-substrate:	0.052
CYP3A4-inhibitor:	0.133
CYP3A4-substrate:	0.133

ADMET: Excretion

Clearance (CL):	2.89
Half-life (T1/2):	0.915

ADMET: Toxicity

hERG Blockers:	0.002
Human Hepatotoxicity (H-HT):	0.382
Drug-inuced Liver Injury (DILI):	0.636
AMES Toxicity:	0.01
Rat Oral Acute Toxicity:	0.746
Maximum Recommended Daily Dose:	0.916
Skin Sensitization:	0.059
Carcinogencity:	0.149
Eye Corrosion:	0.429
Eye Irritation:	0.086
Respiratory Toxicity:	0.043

Download Data

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

Natural Product: NPC472933

Natural Product ID:	NPC472933
*Common Name:**	IOWUVXAOWFISEL-PKNWOKOSSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	IOWUVXAOWFISEL-PKNWOKOSSA-N
Standard InCHI:	InChI=1S/C38H52O13/c1-19(10-9-11-20(2)33(47)48)22-14-26(42)38(8)29-23(40)15-24-35(5,30(29)31(46)32(37(22,38)7)51-21(3)39)13-12-25(41)36(24,6)18-50-28(45)17-34(4,49)16-27(43)44/h11,19,22-24,32,40,49H,9-10,12-18H2,1-8H3,(H,43,44)(H,47,48)/b20-11+/t19-,22-,23+,24-,32+,34+,35+,36+,37+,38+/m1/s1
SMILES:	CC(=O)O[C@H]1C(=O)C2=C([C@]3([C@@]1(C)[C@H](CC3=O)[C@@H](CC/C=C(/C(=O)O)C)C)C)[C@@H](O)C[C@@H]1[C@]2(C)CCC(=O)[C@@]1(C)COC(=O)C[C@](CC(=O)O)(O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3594151
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
NPO33020	ganoderma leucocontextum	Species	Ganodermataceae	Eukaryota	fruiting bodies	Tibetan	n.a.	PMID[26287401]

☑ 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	4

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

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1088	Individual Protein	3-hydroxy-3-methylglutaryl-coenzyme A reductase	Sus scrofa	IC50	=	26400.0	nM	PMID[541383]
NPT111	Cell Line	K562	Homo sapiens	IC50	=	12300.0	nM	PMID[541383]
NPT306	Cell Line	PC-3	Homo sapiens	IC50	=	110500.0	nM	PMID[541383]
NPT2	Others	Unspecified		IC50	>	50000.0	nM	PMID[541383]

☑ 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 NPC472933 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	217
0.1-0.2	1299
0.2-0.3	4623
0.3-0.4	8076
0.4-0.5	12578
0.5-0.6	7445
0.6-0.7	6067
0.7-0.8	2210
0.8-0.85	152
0.85-0.9	24
0.9-0.95	2
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9817	High Similarity	NPC472927
0.9636	High Similarity	NPC472934
0.9541	High Similarity	NPC472926
0.9364	High Similarity	NPC472929
0.9358	High Similarity	NPC472928
0.9266	High Similarity	NPC129689
0.9182	High Similarity	NPC115303
0.9174	High Similarity	NPC77947
0.9174	High Similarity	NPC286174
0.8991	High Similarity	NPC472925
0.8909	High Similarity	NPC295244
0.8783	High Similarity	NPC239273
0.875	High Similarity	NPC272898
0.875	High Similarity	NPC473036
0.8727	High Similarity	NPC472935
0.8727	High Similarity	NPC51452
0.8716	High Similarity	NPC251017
0.8696	High Similarity	NPC148458
0.8661	High Similarity	NPC304495
0.8636	High Similarity	NPC135854
0.8636	High Similarity	NPC470251
0.8636	High Similarity	NPC2436
0.8636	High Similarity	NPC216245
0.8624	High Similarity	NPC475558
0.8624	High Similarity	NPC473788
0.8624	High Similarity	NPC293753
0.8621	High Similarity	NPC471854
0.8596	High Similarity	NPC147180
0.8596	High Similarity	NPC264634
0.8559	High Similarity	NPC109973
0.8548	High Similarity	NPC469674
0.8547	High Similarity	NPC21326
0.8545	High Similarity	NPC70967
0.8545	High Similarity	NPC33973
0.8534	High Similarity	NPC270958
0.8532	High Similarity	NPC472924
0.8522	High Similarity	NPC202889
0.8482	Intermediate Similarity	NPC473037
0.8475	Intermediate Similarity	NPC268958
0.8468	Intermediate Similarity	NPC96268
0.8455	Intermediate Similarity	NPC308726
0.8455	Intermediate Similarity	NPC234892
0.8455	Intermediate Similarity	NPC119601
0.8455	Intermediate Similarity	NPC281702
0.8455	Intermediate Similarity	NPC53222
0.8448	Intermediate Similarity	NPC470953
0.8443	Intermediate Similarity	NPC470882
0.8443	Intermediate Similarity	NPC473265
0.844	Intermediate Similarity	NPC307954
0.844	Intermediate Similarity	NPC287833
0.844	Intermediate Similarity	NPC327431
0.8435	Intermediate Similarity	NPC280782
0.8435	Intermediate Similarity	NPC475524
0.8435	Intermediate Similarity	NPC221144
0.8435	Intermediate Similarity	NPC100267
0.8417	Intermediate Similarity	NPC222688
0.8403	Intermediate Similarity	NPC476962
0.8393	Intermediate Similarity	NPC196528
0.839	Intermediate Similarity	NPC257457
0.839	Intermediate Similarity	NPC311554
0.839	Intermediate Similarity	NPC118638
0.8378	Intermediate Similarity	NPC159442
0.8364	Intermediate Similarity	NPC124211
0.8364	Intermediate Similarity	NPC163372
0.8364	Intermediate Similarity	NPC302537
0.8362	Intermediate Similarity	NPC52634
0.8362	Intermediate Similarity	NPC962
0.8362	Intermediate Similarity	NPC159333
0.8348	Intermediate Similarity	NPC34315
0.8347	Intermediate Similarity	NPC469789
0.8347	Intermediate Similarity	NPC120724
0.8347	Intermediate Similarity	NPC67251
0.8333	Intermediate Similarity	NPC470921
0.8333	Intermediate Similarity	NPC46570
0.8333	Intermediate Similarity	NPC202051
0.832	Intermediate Similarity	NPC102316
0.8319	Intermediate Similarity	NPC475294
0.8319	Intermediate Similarity	NPC476960
0.8319	Intermediate Similarity	NPC185
0.8306	Intermediate Similarity	NPC470880
0.8305	Intermediate Similarity	NPC243065
0.8293	Intermediate Similarity	NPC473253
0.8288	Intermediate Similarity	NPC136289
0.8279	Intermediate Similarity	NPC8369
0.8279	Intermediate Similarity	NPC476729
0.8279	Intermediate Similarity	NPC470922
0.8279	Intermediate Similarity	NPC24651
0.8276	Intermediate Similarity	NPC170487
0.8276	Intermediate Similarity	NPC71348
0.8273	Intermediate Similarity	NPC51370
0.8273	Intermediate Similarity	NPC144660
0.8273	Intermediate Similarity	NPC299971
0.8273	Intermediate Similarity	NPC88198
0.8273	Intermediate Similarity	NPC241221
0.8273	Intermediate Similarity	NPC157787
0.8273	Intermediate Similarity	NPC476274
0.8273	Intermediate Similarity	NPC472972
0.8264	Intermediate Similarity	NPC269642
0.8264	Intermediate Similarity	NPC23786
0.8264	Intermediate Similarity	NPC107493
0.8264	Intermediate Similarity	NPC19464
0.8264	Intermediate Similarity	NPC470265
0.8261	Intermediate Similarity	NPC197428
0.8257	Intermediate Similarity	NPC121339
0.8257	Intermediate Similarity	NPC122294
0.8257	Intermediate Similarity	NPC320306
0.8257	Intermediate Similarity	NPC43747
0.825	Intermediate Similarity	NPC476961
0.825	Intermediate Similarity	NPC17938
0.8246	Intermediate Similarity	NPC322903
0.824	Intermediate Similarity	NPC220757
0.824	Intermediate Similarity	NPC196921
0.8235	Intermediate Similarity	NPC470776
0.8235	Intermediate Similarity	NPC17772
0.8235	Intermediate Similarity	NPC251310
0.823	Intermediate Similarity	NPC323834
0.823	Intermediate Similarity	NPC475494
0.8226	Intermediate Similarity	NPC476859
0.822	Intermediate Similarity	NPC49492
0.822	Intermediate Similarity	NPC270929
0.822	Intermediate Similarity	NPC266728
0.822	Intermediate Similarity	NPC476963
0.8214	Intermediate Similarity	NPC249187
0.8214	Intermediate Similarity	NPC247957
0.8214	Intermediate Similarity	NPC478057
0.8214	Intermediate Similarity	NPC95899
0.8214	Intermediate Similarity	NPC275583
0.8211	Intermediate Similarity	NPC293112
0.8211	Intermediate Similarity	NPC473635
0.8205	Intermediate Similarity	NPC250109
0.8205	Intermediate Similarity	NPC122056
0.8205	Intermediate Similarity	NPC326264
0.8205	Intermediate Similarity	NPC25909
0.8198	Intermediate Similarity	NPC81530
0.8198	Intermediate Similarity	NPC476223
0.8198	Intermediate Similarity	NPC476240
0.8198	Intermediate Similarity	NPC473514
0.8198	Intermediate Similarity	NPC224720
0.8197	Intermediate Similarity	NPC91693
0.8197	Intermediate Similarity	NPC265557
0.8197	Intermediate Similarity	NPC11895
0.8197	Intermediate Similarity	NPC105926
0.8197	Intermediate Similarity	NPC18945
0.819	Intermediate Similarity	NPC214797
0.819	Intermediate Similarity	NPC231589
0.819	Intermediate Similarity	NPC470281
0.819	Intermediate Similarity	NPC43775
0.819	Intermediate Similarity	NPC118860
0.8182	Intermediate Similarity	NPC275439
0.8182	Intermediate Similarity	NPC16021
0.8182	Intermediate Similarity	NPC112753
0.8182	Intermediate Similarity	NPC472401
0.8182	Intermediate Similarity	NPC67569
0.8174	Intermediate Similarity	NPC250018
0.8174	Intermediate Similarity	NPC20192
0.8167	Intermediate Similarity	NPC470777
0.8165	Intermediate Similarity	NPC96859
0.8165	Intermediate Similarity	NPC328162
0.8165	Intermediate Similarity	NPC472941
0.8165	Intermediate Similarity	NPC456
0.8165	Intermediate Similarity	NPC7124
0.8165	Intermediate Similarity	NPC3772
0.8165	Intermediate Similarity	NPC328371
0.8165	Intermediate Similarity	NPC305483
0.816	Intermediate Similarity	NPC35109
0.816	Intermediate Similarity	NPC221414
0.8158	Intermediate Similarity	NPC176949
0.8158	Intermediate Similarity	NPC44063
0.8158	Intermediate Similarity	NPC91034
0.8158	Intermediate Similarity	NPC201908
0.8151	Intermediate Similarity	NPC476959
0.8145	Intermediate Similarity	NPC42399
0.8142	Intermediate Similarity	NPC28656
0.8142	Intermediate Similarity	NPC72255
0.8142	Intermediate Similarity	NPC98603
0.8136	Intermediate Similarity	NPC473798
0.8136	Intermediate Similarity	NPC147912
0.8136	Intermediate Similarity	NPC238667
0.8136	Intermediate Similarity	NPC67259
0.8136	Intermediate Similarity	NPC474181
0.813	Intermediate Similarity	NPC81736
0.813	Intermediate Similarity	NPC473255
0.813	Intermediate Similarity	NPC172154
0.812	Intermediate Similarity	NPC269530
0.812	Intermediate Similarity	NPC317687
0.8115	Intermediate Similarity	NPC312833
0.8115	Intermediate Similarity	NPC170538
0.8115	Intermediate Similarity	NPC470419
0.811	Intermediate Similarity	NPC469673
0.811	Intermediate Similarity	NPC58029
0.811	Intermediate Similarity	NPC168879
0.8108	Intermediate Similarity	NPC198880
0.8103	Intermediate Similarity	NPC286880
0.8095	Intermediate Similarity	NPC476852
0.8095	Intermediate Similarity	NPC476855
0.8092	Intermediate Similarity	NPC25887
0.8091	Intermediate Similarity	NPC216904
0.8091	Intermediate Similarity	NPC106557
0.8087	Intermediate Similarity	NPC65941
0.8087	Intermediate Similarity	NPC472218

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 NPC472933 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	187
0.1-0.2	1618
0.2-0.3	3808
0.3-0.4	2289
0.4-0.5	742
0.5-0.6	222
0.6-0.7	177
0.7-0.8	107
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
0.8348	Intermediate Similarity	NPD6650	Approved
0.8348	Intermediate Similarity	NPD6649	Approved
0.8333	Intermediate Similarity	NPD6373	Approved
0.8333	Intermediate Similarity	NPD6372	Approved
0.8276	Intermediate Similarity	NPD8297	Approved
0.825	Intermediate Similarity	NPD6319	Approved
0.8246	Intermediate Similarity	NPD6881	Approved
0.8246	Intermediate Similarity	NPD6899	Approved
0.823	Intermediate Similarity	NPD6675	Approved
0.823	Intermediate Similarity	NPD5739	Approved
0.823	Intermediate Similarity	NPD7128	Approved
0.823	Intermediate Similarity	NPD6402	Approved
0.819	Intermediate Similarity	NPD8130	Phase 1
0.8158	Intermediate Similarity	NPD5697	Approved
0.812	Intermediate Similarity	NPD6882	Approved
0.8103	Intermediate Similarity	NPD7102	Approved
0.8103	Intermediate Similarity	NPD7290	Approved
0.8103	Intermediate Similarity	NPD6883	Approved
0.8087	Intermediate Similarity	NPD7320	Approved
0.8034	Intermediate Similarity	NPD6869	Approved
0.8034	Intermediate Similarity	NPD6847	Approved
0.8034	Intermediate Similarity	NPD6617	Approved
0.8017	Intermediate Similarity	NPD6014	Approved
0.8017	Intermediate Similarity	NPD6012	Approved
0.8017	Intermediate Similarity	NPD6013	Approved
0.8	Intermediate Similarity	NPD5701	Approved
0.8	Intermediate Similarity	NPD7115	Discovery
0.7984	Intermediate Similarity	NPD7492	Approved
0.7951	Intermediate Similarity	NPD6054	Approved
0.7937	Intermediate Similarity	NPD7736	Approved
0.7931	Intermediate Similarity	NPD6011	Approved
0.792	Intermediate Similarity	NPD6616	Approved
0.7857	Intermediate Similarity	NPD8293	Discontinued
0.7857	Intermediate Similarity	NPD7078	Approved
0.7857	Intermediate Similarity	NPD5696	Approved
0.7823	Intermediate Similarity	NPD6370	Approved
0.7807	Intermediate Similarity	NPD5211	Phase 2
0.7805	Intermediate Similarity	NPD6059	Approved
0.7768	Intermediate Similarity	NPD6083	Phase 2
0.7768	Intermediate Similarity	NPD6084	Phase 2
0.775	Intermediate Similarity	NPD4632	Approved
0.7748	Intermediate Similarity	NPD5695	Phase 3
0.7742	Intermediate Similarity	NPD6015	Approved
0.7742	Intermediate Similarity	NPD6016	Approved
0.7731	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7705	Intermediate Similarity	NPD6009	Approved
0.768	Intermediate Similarity	NPD5988	Approved
0.7672	Intermediate Similarity	NPD5141	Approved
0.7647	Intermediate Similarity	NPD4634	Approved
0.7632	Intermediate Similarity	NPD5286	Approved
0.7632	Intermediate Similarity	NPD7640	Approved
0.7632	Intermediate Similarity	NPD7639	Approved
0.7632	Intermediate Similarity	NPD4696	Approved
0.7632	Intermediate Similarity	NPD5285	Approved
0.7623	Intermediate Similarity	NPD6274	Approved
0.7619	Intermediate Similarity	NPD8328	Phase 3
0.7619	Intermediate Similarity	NPD7604	Phase 2
0.7611	Intermediate Similarity	NPD4755	Approved
0.7607	Intermediate Similarity	NPD6008	Approved
0.76	Intermediate Similarity	NPD5983	Phase 2
0.7581	Intermediate Similarity	NPD7101	Approved
0.7581	Intermediate Similarity	NPD7100	Approved
0.7544	Intermediate Similarity	NPD7638	Approved
0.7522	Intermediate Similarity	NPD4697	Phase 3
0.7522	Intermediate Similarity	NPD5221	Approved
0.7522	Intermediate Similarity	NPD5222	Approved
0.7522	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD5225	Approved
0.75	Intermediate Similarity	NPD4633	Approved
0.75	Intermediate Similarity	NPD6336	Discontinued
0.75	Intermediate Similarity	NPD5226	Approved
0.75	Intermediate Similarity	NPD6335	Approved
0.75	Intermediate Similarity	NPD5224	Approved
0.748	Intermediate Similarity	NPD6868	Approved
0.7478	Intermediate Similarity	NPD4700	Approved
0.7477	Intermediate Similarity	NPD6079	Approved
0.7456	Intermediate Similarity	NPD5173	Approved
0.7455	Intermediate Similarity	NPD5328	Approved
0.7436	Intermediate Similarity	NPD5175	Approved
0.7436	Intermediate Similarity	NPD5174	Approved
0.7434	Intermediate Similarity	NPD4629	Approved
0.7434	Intermediate Similarity	NPD5210	Approved
0.7419	Intermediate Similarity	NPD6317	Approved
0.7414	Intermediate Similarity	NPD5223	Approved
0.7411	Intermediate Similarity	NPD5778	Approved
0.7411	Intermediate Similarity	NPD5779	Approved
0.7411	Intermediate Similarity	NPD6399	Phase 3
0.7364	Intermediate Similarity	NPD6672	Approved
0.7364	Intermediate Similarity	NPD5737	Approved
0.736	Intermediate Similarity	NPD6314	Approved
0.736	Intermediate Similarity	NPD6313	Approved
0.7348	Intermediate Similarity	NPD7260	Phase 2
0.7333	Intermediate Similarity	NPD4729	Approved
0.7333	Intermediate Similarity	NPD4730	Approved
0.7328	Intermediate Similarity	NPD7319	Approved
0.7323	Intermediate Similarity	NPD6908	Approved
0.7323	Intermediate Similarity	NPD6909	Approved
0.7311	Intermediate Similarity	NPD4768	Approved
0.7311	Intermediate Similarity	NPD4767	Approved
0.728	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7252	Intermediate Similarity	NPD6033	Approved
0.7241	Intermediate Similarity	NPD4225	Approved
0.7236	Intermediate Similarity	NPD6053	Discontinued
0.7231	Intermediate Similarity	NPD7507	Approved
0.7213	Intermediate Similarity	NPD5247	Approved
0.7213	Intermediate Similarity	NPD5249	Phase 3
0.7213	Intermediate Similarity	NPD5248	Approved
0.7213	Intermediate Similarity	NPD5251	Approved
0.7213	Intermediate Similarity	NPD5250	Approved
0.7193	Intermediate Similarity	NPD7748	Approved
0.719	Intermediate Similarity	NPD5128	Approved
0.719	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD6291	Clinical (unspecified phase)
0.7182	Intermediate Similarity	NPD3618	Phase 1
0.7168	Intermediate Similarity	NPD6050	Approved
0.7168	Intermediate Similarity	NPD6411	Approved
0.7155	Intermediate Similarity	NPD7902	Approved
0.7143	Intermediate Similarity	NPD6673	Approved
0.7143	Intermediate Similarity	NPD6904	Approved
0.7143	Intermediate Similarity	NPD4754	Approved
0.7143	Intermediate Similarity	NPD6080	Approved
0.7143	Intermediate Similarity	NPD4753	Phase 2
0.708	Intermediate Similarity	NPD5692	Phase 3
0.7059	Intermediate Similarity	NPD7632	Discontinued
0.7037	Intermediate Similarity	NPD6845	Suspended
0.7027	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD5279	Phase 3
0.7018	Intermediate Similarity	NPD5693	Phase 1
0.7018	Intermediate Similarity	NPD7637	Suspended
0.7018	Intermediate Similarity	NPD5694	Approved
0.7018	Intermediate Similarity	NPD7515	Phase 2
0.7016	Intermediate Similarity	NPD5216	Approved
0.7016	Intermediate Similarity	NPD5217	Approved
0.7016	Intermediate Similarity	NPD5215	Approved
0.7	Intermediate Similarity	NPD4786	Approved
0.6991	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6991	Remote Similarity	NPD6101	Approved
0.6983	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6967	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD4202	Approved
0.6935	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6935	Remote Similarity	NPD6371	Approved
0.6935	Remote Similarity	NPD5169	Approved
0.6935	Remote Similarity	NPD5135	Approved
0.6935	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.693	Remote Similarity	NPD5785	Approved
0.6923	Remote Similarity	NPD8513	Phase 3
0.6923	Remote Similarity	NPD8516	Approved
0.6923	Remote Similarity	NPD8517	Approved
0.6923	Remote Similarity	NPD8515	Approved
0.6911	Remote Similarity	NPD5168	Approved
0.6911	Remote Similarity	NPD6686	Approved
0.6906	Remote Similarity	NPD6333	Approved
0.6906	Remote Similarity	NPD6334	Approved
0.6897	Remote Similarity	NPD7900	Approved
0.6897	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.688	Remote Similarity	NPD5127	Approved
0.6875	Remote Similarity	NPD6098	Approved
0.6875	Remote Similarity	NPD6684	Approved
0.6875	Remote Similarity	NPD5690	Phase 2
0.6875	Remote Similarity	NPD7334	Approved
0.6875	Remote Similarity	NPD6409	Approved
0.6875	Remote Similarity	NPD7146	Approved
0.6875	Remote Similarity	NPD5330	Approved
0.6875	Remote Similarity	NPD7521	Approved
0.687	Remote Similarity	NPD8034	Phase 2
0.687	Remote Similarity	NPD5284	Approved
0.687	Remote Similarity	NPD5281	Approved
0.687	Remote Similarity	NPD8035	Phase 2
0.6855	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6855	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD6412	Phase 2
0.6829	Remote Similarity	NPD6614	Approved
0.6818	Remote Similarity	NPD3667	Approved
0.6814	Remote Similarity	NPD3573	Approved
0.6794	Remote Similarity	NPD8033	Approved
0.6786	Remote Similarity	NPD5363	Approved
0.6786	Remote Similarity	NPD5329	Approved
0.6754	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6754	Remote Similarity	NPD6903	Approved
0.6752	Remote Similarity	NPD5282	Discontinued
0.6726	Remote Similarity	NPD5786	Approved
0.6726	Remote Similarity	NPD4694	Approved
0.6726	Remote Similarity	NPD5280	Approved
0.6724	Remote Similarity	NPD7983	Approved
0.6719	Remote Similarity	NPD5167	Approved
0.6718	Remote Similarity	NPD8377	Approved
0.6718	Remote Similarity	NPD8294	Approved
0.6696	Remote Similarity	NPD4197	Approved
0.6696	Remote Similarity	NPD3665	Phase 1
0.6696	Remote Similarity	NPD3133	Approved
0.6696	Remote Similarity	NPD3666	Approved
0.6695	Remote Similarity	NPD5654	Approved
0.6695	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6694	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6692	Remote Similarity	NPD7327	Approved
0.6692	Remote Similarity	NPD7328	Approved
0.6667	Remote Similarity	NPD8380	Approved
0.6667	Remote Similarity	NPD8335	Approved
0.6667	Remote Similarity	NPD7503	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