NPASS Compound

Structure

NPC106593 OpenBabel07101718292D 50 56 0 0 1 0 0 0 0 0999 V2000 -0.5653 -2.1407 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0567 -0.3679 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4209 -2.5962 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1432 -6.3912 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6764 -0.0861 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4424 1.8328 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4206 -1.9731 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6718 0.1274 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7781 -0.8670 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7575 0.5324 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9702 -1.4562 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5464 -3.2241 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6527 -4.2184 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5370 -0.8506 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6438 -0.6287 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2348 -1.0314 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3385 0.2485 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3130 -0.9431 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3130 0.1640 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9495 -0.0569 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2419 -0.9120 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6551 -0.1240 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.0559 -1.0512 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3277 -0.4715 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.2914 -0.8690 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.3543 -2.6348 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8448 -4.8077 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9221 0.5561 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0487 0.0691 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.1527 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.5764 0.3328 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.0352 0.3482 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4161 -0.6103 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.5051 -0.4253 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.2177 0.7059 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.1527 -0.6655 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 4.2480 -1.6405 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.7685 -1.0356 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 5.2686 -3.0398 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.9305 -4.4026 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.9289 1.3425 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.2707 1.7045 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9427 -0.3336 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2221 -0.9188 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8575 -1.7699 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.9511 -5.8020 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8587 0.4895 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.5764 1.3328 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.2273 -0.2411 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 7 1 0 0 0 0 2 45 1 0 0 0 0 3 46 1 0 0 0 0 4 47 1 0 0 0 0 5 48 1 0 0 0 0 6 49 1 0 0 0 0 7 39 1 0 0 0 0 8 9 2 0 0 0 0 8 10 1 0 0 0 0 9 11 1 0 0 0 0 10 20 2 0 0 0 0 11 23 2 0 0 0 0 12 13 1 0 0 0 0 12 26 1 0 0 0 0 13 27 1 0 0 0 0 14 15 1 0 0 0 0 14 25 1 0 0 0 0 15 34 1 0 0 0 0 16 22 1 0 0 0 0 17 24 1 0 0 0 0 17 35 1 0 0 0 0 18 34 1 0 0 0 0 18 39 1 0 0 0 0 19 50 1 0 0 0 0 20 23 1 0 0 0 0 20 32 1 0 0 0 0 21 16 1 6 0 0 0 21 24 1 0 0 0 0 21 29 1 0 0 0 0 22 28 1 0 0 0 0 22 36 1 6 0 0 0 23 38 1 0 0 0 0 24 45 1 1 0 0 0 25 36 1 6 0 0 0 25 46 1 0 0 0 0 26 38 2 3 0 0 0 26 40 1 0 0 0 0 27 41 2 0 0 0 0 27 47 1 0 0 0 0 28 29 1 0 0 0 0 28 35 1 6 0 0 0 29 48 1 6 0 0 0 30 31 1 0 0 0 0 30 34 1 6 0 0 0 30 36 1 0 0 0 0 31 37 1 1 0 0 0 31 49 1 0 0 0 0 32 42 2 0 0 0 0 32 50 1 0 0 0 0 33 36 1 1 0 0 0 33 37 1 0 0 0 0 33 39 1 0 0 0 0 34 19 1 6 0 0 0 35 37 1 6 0 0 0 35 43 1 0 0 0 0 37 44 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	700.36
Volume:	691.48
LogP:	2.318
LogD:	2.707
LogS:	-4.398
# Rotatable Bonds:	15
TPSA:	162.32
# H-Bond Aceptor:	13
# H-Bond Donor:	3
# Rings:	7
# Heavy Atoms:	13

MedChem Properties

QED Drug-Likeness Score:	0.273
Synthetic Accessibility Score:	7.067
Fsp3:	0.757
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:	-5.409
MDCK Permeability:	5.814221367472783e-05
Pgp-inhibitor:	0.989
Pgp-substrate:	0.998
Human Intestinal Absorption (HIA):	0.506
20% Bioavailability (F20%):	0.073
30% Bioavailability (F30%):	0.842

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.14
Plasma Protein Binding (PPB):	27.26226234436035%
Volume Distribution (VD):	0.534
Pgp-substrate:	38.135780334472656%

ADMET: Metabolism

CYP1A2-inhibitor:	0.003
CYP1A2-substrate:	0.95
CYP2C19-inhibitor:	0.004
CYP2C19-substrate:	0.358
CYP2C9-inhibitor:	0.006
CYP2C9-substrate:	0.007
CYP2D6-inhibitor:	0.011
CYP2D6-substrate:	0.149
CYP3A4-inhibitor:	0.343
CYP3A4-substrate:	0.657

ADMET: Excretion

Clearance (CL):	6.32
Half-life (T1/2):	0.55

ADMET: Toxicity

hERG Blockers:	0.506
Human Hepatotoxicity (H-HT):	0.3
Drug-inuced Liver Injury (DILI):	0.211
AMES Toxicity:	0.061
Rat Oral Acute Toxicity:	0.071
Maximum Recommended Daily Dose:	0.045
Skin Sensitization:	0.129
Carcinogencity:	0.053
Eye Corrosion:	0.003
Eye Irritation:	0.007
Respiratory Toxicity:	0.967

Download Data

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

Natural Product: NPC106593

Natural Product ID:	NPC106593
*Common Name:**	Cashmiradelphine
IUPAC Name:	n.a.
Synonyms:	Cashmiradelphine
Standard InCHIKey:	SVMCGAKQNRLCHV-VSNJHZSNSA-N
Standard InCHI:	InChI=1S/C37H52N2O11/c1-7-39-18-34(19-50-32(42)20-10-8-9-11-23(20)38-26(40)12-13-27(41)47-4)15-14-25(46-3)36-22-16-21-24(45-2)17-35(43,28(22)29(21)48-5)37(44,33(36)39)31(49-6)30(34)36/h8-11,21-22,24-25,28-31,33,43-44H,7,12-19H2,1-6H3,(H,38,40)/t21-,22-,24+,25+,28-,29+,30-,31+,33+,34+,35-,36+,37+/m1/s1
SMILES:	COC(=O)CCC(=Nc1ccccc1C(=O)OC[C@]12CC[C@@H]([C@@]34[C@@H]2[C@H](OC)[C@@]([C@H]3N(C1)CC)(O)[C@@]1([C@@H]2[C@H]4C[C@@H]([C@@H]2OC)[C@H](C1)OC)O)OC)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL454965
PubChem CID:	44566472
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0003788] Aconitane-type diterpenoid alkaloids

*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
NPO33014	delphinium cashmirianum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[541686]

☑ 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
Others	7

Activity Type	# Activity
Organism	7

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT419	Organism	Oryctolagus cuniculus	Oryctolagus cuniculus	Activity	=	-5.0	bpm	PMID[494391]
NPT419	Organism	Oryctolagus cuniculus	Oryctolagus cuniculus	Activity	=	5.0	bpm	PMID[494391]
NPT419	Organism	Oryctolagus cuniculus	Oryctolagus cuniculus	Activity	=	-20.0	bpm	PMID[494391]
NPT419	Organism	Oryctolagus cuniculus	Oryctolagus cuniculus	Activity	=	-8.0	bpm	PMID[494391]
NPT419	Organism	Oryctolagus cuniculus	Oryctolagus cuniculus	Activity	=	-10.0	bpm	PMID[494391]

☑ 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 NPC106593 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	344
0.1-0.2	1481
0.2-0.3	3287
0.3-0.4	10250
0.4-0.5	19701
0.5-0.6	6153
0.6-0.7	1291
0.7-0.8	143
0.8-0.85	16
0.85-0.9	23
0.9-0.95	4
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9849	High Similarity	NPC473667
0.96	High Similarity	NPC140311
0.955	High Similarity	NPC223590
0.9163	High Similarity	NPC473837
0.9095	High Similarity	NPC35390
0.9095	High Similarity	NPC470631
0.9095	High Similarity	NPC473781
0.9052	High Similarity	NPC473486
0.9052	High Similarity	NPC475316
0.8492	Intermediate Similarity	NPC166521
0.8492	Intermediate Similarity	NPC281470
0.8492	Intermediate Similarity	NPC184195
0.8492	Intermediate Similarity	NPC172769
0.8492	Intermediate Similarity	NPC205
0.8492	Intermediate Similarity	NPC124690
0.8392	Intermediate Similarity	NPC40539
0.835	Intermediate Similarity	NPC108276
0.835	Intermediate Similarity	NPC163578
0.7934	Intermediate Similarity	NPC476496
0.784	Intermediate Similarity	NPC326895
0.7804	Intermediate Similarity	NPC94687
0.7804	Intermediate Similarity	NPC476495
0.7804	Intermediate Similarity	NPC106840
0.757	Intermediate Similarity	NPC475223
0.7535	Intermediate Similarity	NPC475448
0.7535	Intermediate Similarity	NPC246983
0.7435	Intermediate Similarity	NPC475596
0.7435	Intermediate Similarity	NPC475303
0.7435	Intermediate Similarity	NPC316841
0.7434	Intermediate Similarity	NPC127720
0.7434	Intermediate Similarity	NPC127026
0.7414	Intermediate Similarity	NPC475406
0.7403	Intermediate Similarity	NPC30456
0.7401	Intermediate Similarity	NPC471980
0.7382	Intermediate Similarity	NPC327904
0.7382	Intermediate Similarity	NPC38959
0.738	Intermediate Similarity	NPC228377
0.738	Intermediate Similarity	NPC122968
0.738	Intermediate Similarity	NPC477787
0.738	Intermediate Similarity	NPC476110
0.738	Intermediate Similarity	NPC475631
0.738	Intermediate Similarity	NPC328186
0.738	Intermediate Similarity	NPC475600
0.738	Intermediate Similarity	NPC87152
0.7378	Intermediate Similarity	NPC84815
0.7378	Intermediate Similarity	NPC301368
0.7359	Intermediate Similarity	NPC473689
0.7359	Intermediate Similarity	NPC292416
0.7348	Intermediate Similarity	NPC470486
0.7348	Intermediate Similarity	NPC475644
0.7348	Intermediate Similarity	NPC471977
0.7348	Intermediate Similarity	NPC471190
0.7339	Intermediate Similarity	NPC327769
0.7333	Intermediate Similarity	NPC62367
0.7328	Intermediate Similarity	NPC244839
0.7328	Intermediate Similarity	NPC320324
0.7328	Intermediate Similarity	NPC319880
0.7325	Intermediate Similarity	NPC76565
0.7325	Intermediate Similarity	NPC57797
0.7325	Intermediate Similarity	NPC250807
0.7324	Intermediate Similarity	NPC198205
0.7324	Intermediate Similarity	NPC21483
0.7304	Intermediate Similarity	NPC211920
0.7304	Intermediate Similarity	NPC146824
0.7301	Intermediate Similarity	NPC216428
0.7296	Intermediate Similarity	NPC237702
0.7293	Intermediate Similarity	NPC475137
0.7293	Intermediate Similarity	NPC475498
0.7293	Intermediate Similarity	NPC477902
0.7293	Intermediate Similarity	NPC473850
0.7289	Intermediate Similarity	NPC6981
0.7289	Intermediate Similarity	NPC471016
0.7273	Intermediate Similarity	NPC475362
0.7269	Intermediate Similarity	NPC475648
0.7265	Intermediate Similarity	NPC170751
0.7261	Intermediate Similarity	NPC473506
0.7257	Intermediate Similarity	NPC473089
0.7257	Intermediate Similarity	NPC158020
0.7257	Intermediate Similarity	NPC144779
0.7257	Intermediate Similarity	NPC6576
0.7257	Intermediate Similarity	NPC212768
0.7257	Intermediate Similarity	NPC294579
0.7257	Intermediate Similarity	NPC473115
0.7257	Intermediate Similarity	NPC75600
0.7256	Intermediate Similarity	NPC198390
0.7251	Intermediate Similarity	NPC327699
0.7244	Intermediate Similarity	NPC477909
0.7244	Intermediate Similarity	NPC470306
0.7244	Intermediate Similarity	NPC42678
0.7244	Intermediate Similarity	NPC477907
0.7243	Intermediate Similarity	NPC476256
0.7243	Intermediate Similarity	NPC476257
0.7243	Intermediate Similarity	NPC476206
0.7243	Intermediate Similarity	NPC476205
0.7243	Intermediate Similarity	NPC476212
0.7243	Intermediate Similarity	NPC476129
0.7243	Intermediate Similarity	NPC259791
0.7243	Intermediate Similarity	NPC476207
0.7237	Intermediate Similarity	NPC477912
0.7229	Intermediate Similarity	NPC124029
0.7222	Intermediate Similarity	NPC311054
0.7222	Intermediate Similarity	NPC112752
0.7217	Intermediate Similarity	NPC328154
0.7215	Intermediate Similarity	NPC253482
0.7212	Intermediate Similarity	NPC471014
0.7212	Intermediate Similarity	NPC475408
0.7209	Intermediate Similarity	NPC476218
0.7209	Intermediate Similarity	NPC108804
0.7205	Intermediate Similarity	NPC477788
0.7202	Intermediate Similarity	NPC136573
0.7202	Intermediate Similarity	NPC176371
0.72	Intermediate Similarity	NPC4421
0.7189	Intermediate Similarity	NPC107828
0.7189	Intermediate Similarity	NPC90358
0.7188	Intermediate Similarity	NPC472553
0.7186	Intermediate Similarity	NPC148860
0.7183	Intermediate Similarity	NPC324251
0.7183	Intermediate Similarity	NPC471629
0.7183	Intermediate Similarity	NPC473400
0.7183	Intermediate Similarity	NPC471754
0.7183	Intermediate Similarity	NPC206211
0.7183	Intermediate Similarity	NPC317882
0.7183	Intermediate Similarity	NPC275170
0.7183	Intermediate Similarity	NPC306001
0.7172	Intermediate Similarity	NPC131273
0.7172	Intermediate Similarity	NPC473441
0.7164	Intermediate Similarity	NPC476750
0.7162	Intermediate Similarity	NPC477903
0.7149	Intermediate Similarity	NPC472555
0.7143	Intermediate Similarity	NPC471583
0.7143	Intermediate Similarity	NPC471782
0.7137	Intermediate Similarity	NPC150698
0.7137	Intermediate Similarity	NPC96801
0.7137	Intermediate Similarity	NPC477906
0.713	Intermediate Similarity	NPC242662
0.713	Intermediate Similarity	NPC321072
0.713	Intermediate Similarity	NPC191193
0.713	Intermediate Similarity	NPC215892
0.7119	Intermediate Similarity	NPC35208
0.7119	Intermediate Similarity	NPC475426
0.7112	Intermediate Similarity	NPC476436
0.7111	Intermediate Similarity	NPC476467
0.7106	Intermediate Similarity	NPC476429
0.7103	Intermediate Similarity	NPC473300
0.7103	Intermediate Similarity	NPC453583
0.7103	Intermediate Similarity	NPC475336
0.7101	Intermediate Similarity	NPC278540
0.7097	Intermediate Similarity	NPC181964
0.7097	Intermediate Similarity	NPC471606
0.7097	Intermediate Similarity	NPC208553
0.7082	Intermediate Similarity	NPC14116
0.7082	Intermediate Similarity	NPC475601
0.7082	Intermediate Similarity	NPC473458
0.7082	Intermediate Similarity	NPC285411
0.7078	Intermediate Similarity	NPC475489
0.7078	Intermediate Similarity	NPC472375
0.7076	Intermediate Similarity	NPC238278
0.7073	Intermediate Similarity	NPC476749
0.7072	Intermediate Similarity	NPC476500
0.707	Intermediate Similarity	NPC33372
0.707	Intermediate Similarity	NPC67246
0.7069	Intermediate Similarity	NPC477899
0.7069	Intermediate Similarity	NPC477900
0.7064	Intermediate Similarity	NPC473558
0.7064	Intermediate Similarity	NPC473490
0.7061	Intermediate Similarity	NPC477908
0.7061	Intermediate Similarity	NPC206343
0.7056	Intermediate Similarity	NPC235364
0.7056	Intermediate Similarity	NPC477911
0.7054	Intermediate Similarity	NPC48042
0.7054	Intermediate Similarity	NPC304179
0.7054	Intermediate Similarity	NPC472550
0.7051	Intermediate Similarity	NPC134384
0.7051	Intermediate Similarity	NPC311196
0.7048	Intermediate Similarity	NPC319128
0.7048	Intermediate Similarity	NPC264674
0.7045	Intermediate Similarity	NPC471512
0.7033	Intermediate Similarity	NPC203005
0.7025	Intermediate Similarity	NPC311451
0.7024	Intermediate Similarity	NPC469462
0.7018	Intermediate Similarity	NPC477910
0.7018	Intermediate Similarity	NPC36607
0.7017	Intermediate Similarity	NPC17160
0.7017	Intermediate Similarity	NPC313720
0.7	Intermediate Similarity	NPC472392
0.6996	Remote Similarity	NPC26881
0.699	Remote Similarity	NPC30171
0.6982	Remote Similarity	NPC289383
0.6977	Remote Similarity	NPC471623
0.6975	Remote Similarity	NPC476220
0.6975	Remote Similarity	NPC160113
0.6974	Remote Similarity	NPC228331
0.697	Remote Similarity	NPC477901
0.6968	Remote Similarity	NPC472391
0.6967	Remote Similarity	NPC475962
0.6962	Remote Similarity	NPC213143
0.6962	Remote Similarity	NPC469748
0.6955	Remote Similarity	NPC476090
0.6951	Remote Similarity	NPC116862
0.6936	Remote Similarity	NPC471513

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 NPC106593 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	193
0.1-0.2	583
0.2-0.3	816
0.3-0.4	2210
0.4-0.5	3726
0.5-0.6	1513
0.6-0.7	106
0.7-0.8	3
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
0.7783	Intermediate Similarity	NPD7497	Discontinued
0.7097	Intermediate Similarity	NPD8485	Approved
0.7014	Intermediate Similarity	NPD8658	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD8486	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD8360	Approved
0.6977	Remote Similarity	NPD8435	Approved
0.6977	Remote Similarity	NPD8361	Approved
0.6963	Remote Similarity	NPD8424	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD8468	Phase 2
0.6825	Remote Similarity	NPD8470	Clinical (unspecified phase)
0.6695	Remote Similarity	NPD6997	Phase 2
0.6682	Remote Similarity	NPD8146	Phase 2
0.6667	Remote Similarity	NPD7795	Phase 2
0.6653	Remote Similarity	NPD6625	Approved
0.6652	Remote Similarity	NPD6874	Approved
0.6636	Remote Similarity	NPD8407	Phase 2
0.6574	Remote Similarity	NPD8368	Discontinued
0.6544	Remote Similarity	NPD7962	Phase 2
0.6511	Remote Similarity	NPD7047	Phase 3
0.6478	Remote Similarity	NPD8161	Suspended
0.6471	Remote Similarity	NPD8492	Approved
0.6463	Remote Similarity	NPD5891	Approved
0.6462	Remote Similarity	NPD7803	Approved
0.6453	Remote Similarity	NPD8462	Phase 1
0.6449	Remote Similarity	NPD7997	Clinical (unspecified phase)
0.6438	Remote Similarity	NPD7546	Discontinued
0.6436	Remote Similarity	NPD7274	Clinical (unspecified phase)
0.6434	Remote Similarity	NPD7708	Approved
0.6429	Remote Similarity	NPD8465	Approved
0.6429	Remote Similarity	NPD8466	Approved
0.6429	Remote Similarity	NPD8467	Approved
0.6416	Remote Similarity	NPD2973	Approved
0.6416	Remote Similarity	NPD7238	Clinical (unspecified phase)
0.6416	Remote Similarity	NPD2975	Approved
0.6416	Remote Similarity	NPD2974	Approved
0.6404	Remote Similarity	NPD4580	Approved
0.6396	Remote Similarity	NPD7906	Approved
0.6395	Remote Similarity	NPD7955	Approved
0.6395	Remote Similarity	NPD7956	Approved
0.6388	Remote Similarity	NPD8364	Approved
0.6388	Remote Similarity	NPD8363	Approved
0.6386	Remote Similarity	NPD7488	Clinical (unspecified phase)
0.6383	Remote Similarity	NPD7827	Phase 1
0.6377	Remote Similarity	NPD6591	Clinical (unspecified phase)
0.6376	Remote Similarity	NPD2494	Approved
0.6376	Remote Similarity	NPD3452	Approved
0.6376	Remote Similarity	NPD3450	Approved
0.6376	Remote Similarity	NPD2493	Approved
0.6375	Remote Similarity	NPD7907	Approved
0.6364	Remote Similarity	NPD4583	Approved
0.6364	Remote Similarity	NPD4582	Approved
0.636	Remote Similarity	NPD7565	Approved
0.6351	Remote Similarity	NPD8103	Clinical (unspecified phase)
0.6348	Remote Similarity	NPD5848	Clinical (unspecified phase)
0.6345	Remote Similarity	NPD8404	Phase 2
0.634	Remote Similarity	NPD8365	Clinical (unspecified phase)
0.6333	Remote Similarity	NPD8460	Approved
0.6333	Remote Similarity	NPD8426	Approved
0.6333	Remote Similarity	NPD8425	Approved
0.6333	Remote Similarity	NPD8459	Approved
0.632	Remote Similarity	NPD4004	Approved
0.632	Remote Similarity	NPD4002	Approved
0.6314	Remote Similarity	NPD8367	Approved
0.6311	Remote Similarity	NPD7569	Approved
0.6311	Remote Similarity	NPD7570	Approved
0.6309	Remote Similarity	NPD6296	Discontinued
0.6306	Remote Similarity	NPD8427	Approved
0.6306	Remote Similarity	NPD8429	Approved
0.6306	Remote Similarity	NPD8428	Approved
0.63	Remote Similarity	NPD8249	Clinical (unspecified phase)
0.6295	Remote Similarity	NPD5928	Phase 1
0.6293	Remote Similarity	NPD8320	Phase 1
0.6293	Remote Similarity	NPD8319	Approved
0.6267	Remote Similarity	NPD6656	Clinical (unspecified phase)
0.6266	Remote Similarity	NPD6807	Phase 3
0.6266	Remote Similarity	NPD3437	Discontinued
0.6266	Remote Similarity	NPD7858	Clinical (unspecified phase)
0.625	Remote Similarity	NPD6723	Discontinued
0.6245	Remote Similarity	NPD7301	Phase 3
0.624	Remote Similarity	NPD7048	Phase 3
0.6239	Remote Similarity	NPD7799	Discontinued
0.6238	Remote Similarity	NPD7702	Clinical (unspecified phase)
0.6235	Remote Similarity	NPD7688	Phase 1
0.6235	Remote Similarity	NPD8067	Phase 3
0.6234	Remote Similarity	NPD8149	Discontinued
0.6233	Remote Similarity	NPD5036	Approved
0.6231	Remote Similarity	NPD8461	Discontinued
0.623	Remote Similarity	NPD7417	Discontinued
0.6224	Remote Similarity	NPD2899	Discontinued
0.6217	Remote Similarity	NPD7811	Phase 3
0.6217	Remote Similarity	NPD5609	Approved
0.6217	Remote Similarity	NPD5608	Approved
0.6217	Remote Similarity	NPD7810	Phase 3
0.6215	Remote Similarity	NPD7591	Clinical (unspecified phase)
0.6213	Remote Similarity	NPD7300	Phase 3
0.6213	Remote Similarity	NPD7302	Phase 3
0.621	Remote Similarity	NPD8006	Clinical (unspecified phase)
0.6207	Remote Similarity	NPD5005	Approved
0.6207	Remote Similarity	NPD5006	Approved
0.6205	Remote Similarity	NPD5037	Approved
0.6205	Remote Similarity	NPD5038	Approved
0.6202	Remote Similarity	NPD7606	Phase 3
0.619	Remote Similarity	NPD5743	Approved
0.619	Remote Similarity	NPD7560	Approved
0.619	Remote Similarity	NPD5741	Approved
0.619	Remote Similarity	NPD5742	Approved
0.6189	Remote Similarity	NPD3912	Discontinued
0.6185	Remote Similarity	NPD7922	Phase 1
0.6174	Remote Similarity	NPD4420	Approved
0.6173	Remote Similarity	NPD8155	Clinical (unspecified phase)
0.6173	Remote Similarity	NPD7556	Discontinued
0.6163	Remote Similarity	NPD6503	Clinical (unspecified phase)
0.6157	Remote Similarity	NPD2821	Approved
0.6157	Remote Similarity	NPD6770	Approved
0.6157	Remote Similarity	NPD7921	Approved
0.6157	Remote Similarity	NPD4111	Phase 1
0.6157	Remote Similarity	NPD4665	Approved
0.6157	Remote Similarity	NPD7667	Clinical (unspecified phase)
0.615	Remote Similarity	NPD6836	Approved
0.6144	Remote Similarity	NPD7701	Phase 2
0.6143	Remote Similarity	NPD4120	Approved
0.6143	Remote Similarity	NPD4578	Approved
0.6143	Remote Similarity	NPD4121	Phase 3
0.6143	Remote Similarity	NPD4577	Approved
0.6138	Remote Similarity	NPD7186	Phase 3
0.6134	Remote Similarity	NPD7927	Clinical (unspecified phase)
0.6134	Remote Similarity	NPD7801	Approved
0.6133	Remote Similarity	NPD4663	Approved
0.6127	Remote Similarity	NPD6414	Clinical (unspecified phase)
0.6117	Remote Similarity	NPD7295	Approved
0.6116	Remote Similarity	NPD7292	Approved
0.6116	Remote Similarity	NPD7293	Approved
0.6116	Remote Similarity	NPD7395	Discontinued
0.6113	Remote Similarity	NPD8059	Phase 3
0.6113	Remote Similarity	NPD8058	Clinical (unspecified phase)
0.6111	Remote Similarity	NPD8002	Clinical (unspecified phase)
0.6111	Remote Similarity	NPD8003	Clinical (unspecified phase)
0.6111	Remote Similarity	NPD7597	Clinical (unspecified phase)
0.6109	Remote Similarity	NPD6657	Clinical (unspecified phase)
0.6109	Remote Similarity	NPD7225	Discontinued
0.6106	Remote Similarity	NPD8389	Clinical (unspecified phase)
0.6103	Remote Similarity	NPD7599	Phase 2
0.61	Remote Similarity	NPD7475	Clinical (unspecified phase)
0.61	Remote Similarity	NPD5025	Approved
0.6095	Remote Similarity	NPD7239	Suspended
0.6089	Remote Similarity	NPD3153	Approved
0.6089	Remote Similarity	NPD3154	Approved
0.6087	Remote Similarity	NPD7236	Approved
0.6087	Remote Similarity	NPD7880	Clinical (unspecified phase)
0.6085	Remote Similarity	NPD2672	Discontinued
0.6085	Remote Similarity	NPD8489	Phase 1
0.6083	Remote Similarity	NPD3794	Approved
0.6083	Remote Similarity	NPD3795	Approved
0.6082	Remote Similarity	NPD6995	Phase 1
0.6078	Remote Similarity	NPD6716	Phase 1
0.6075	Remote Similarity	NPD7600	Phase 2
0.6074	Remote Similarity	NPD8326	Phase 3
0.6074	Remote Similarity	NPD8325	Phase 3
0.6074	Remote Similarity	NPD8327	Clinical (unspecified phase)
0.6073	Remote Similarity	NPD5997	Discontinued
0.6068	Remote Similarity	NPD7487	Discontinued
0.6068	Remote Similarity	NPD8162	Phase 2
0.6068	Remote Similarity	NPD8163	Clinical (unspecified phase)
0.6068	Remote Similarity	NPD5721	Clinical (unspecified phase)
0.6067	Remote Similarity	NPD1945	Phase 1
0.6067	Remote Similarity	NPD5676	Approved
0.6064	Remote Similarity	NPD6199	Discontinued
0.6062	Remote Similarity	NPD7683	Discontinued
0.6061	Remote Similarity	NPD7282	Approved
0.6061	Remote Similarity	NPD4979	Clinical (unspecified phase)
0.6059	Remote Similarity	NPD7174	Clinical (unspecified phase)
0.6059	Remote Similarity	NPD3170	Approved
0.6058	Remote Similarity	NPD7478	Approved
0.6058	Remote Similarity	NPD7559	Phase 2
0.6057	Remote Similarity	NPD5619	Clinical (unspecified phase)
0.6054	Remote Similarity	NPD5029	Approved
0.6054	Remote Similarity	NPD5027	Approved
0.6054	Remote Similarity	NPD5030	Phase 2
0.6054	Remote Similarity	NPD5031	Approved
0.6053	Remote Similarity	NPD5042	Phase 1
0.6052	Remote Similarity	NPD4107	Approved
0.605	Remote Similarity	NPD4506	Discontinued
0.6043	Remote Similarity	NPD7064	Clinical (unspecified phase)
0.6043	Remote Similarity	NPD7256	Discontinued
0.6036	Remote Similarity	NPD5190	Phase 2
0.6036	Remote Similarity	NPD8304	Clinical (unspecified phase)
0.6035	Remote Similarity	NPD6608	Clinical (unspecified phase)
0.6034	Remote Similarity	NPD4987	Clinical (unspecified phase)
0.6034	Remote Similarity	NPD4668	Phase 2
0.6029	Remote Similarity	NPD7528	Approved
0.6027	Remote Similarity	NPD5034	Approved
0.6027	Remote Similarity	NPD4955	Approved
0.6027	Remote Similarity	NPD5026	Approved
0.6027	Remote Similarity	NPD36	Approved
0.6027	Remote Similarity	NPD7687	Clinical (unspecified phase)
0.6027	Remote Similarity	NPD4954	Approved
0.6027	Remote Similarity	NPD5028	Approved
0.6026	Remote Similarity	NPD7566	Clinical (unspecified phase)
0.6026	Remote Similarity	NPD5937	Approved
0.6026	Remote Similarity	NPD7476	Discontinued

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