NPASS Compound

Structure

NPC92196 OpenBabel07101718282D 55 60 0 0 1 0 0 0 0 0999 V2000 -4.2216 -1.7827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5088 -2.9417 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1413 -6.8653 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.2637 -3.6609 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9439 -4.8519 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9271 -2.8532 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5014 -5.1711 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1705 -4.4280 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.9958 -2.6609 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3977 -4.1609 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8833 -3.2690 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.1298 -3.1609 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5317 -4.6609 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5743 -2.3179 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.1298 -6.1609 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2946 1.0705 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9781 0.2079 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5306 -2.7338 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8104 -6.1222 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.8615 -3.4769 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -9.8618 -3.1609 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -8.9958 -5.6609 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6473 -0.5352 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.3164 1.2784 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -7.2637 -4.6609 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.7885 -6.3301 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -8.9958 -4.6609 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -9.8618 -4.1609 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.3383 -1.4863 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6473 0.5352 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.1953 -7.2436 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.1898 -7.1391 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.3601 -1.6942 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.9563 -0.4158 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.3977 -6.1609 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.9344 -0.6237 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.3090 -0.9511 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -8.1298 -4.1609 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.5317 -5.6609 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.2637 -5.6609 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -10.7278 -2.6609 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.8618 -6.1609 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6254 -0.3273 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.0074 2.2294 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.7278 -4.6609 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.0074 -2.2294 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.6691 0.7431 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.6953 -8.1096 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.8589 -7.8822 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.2637 -6.6609 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0511 -2.6453 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.2435 -1.5748 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.6036 0.1194 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 -1.2872 -1.1590 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 18 1 0 0 0 0 2 18 1 0 0 0 0 6 51 1 0 0 0 0 7 8 1 0 0 0 0 7 19 1 0 0 0 0 9 12 1 0 0 0 0 9 21 1 0 0 0 0 10 13 1 0 0 0 0 10 25 1 0 0 0 0 11 14 1 0 0 0 0 11 20 1 0 0 0 0 12 38 1 0 0 0 0 13 39 1 0 0 0 0 14 52 1 0 0 0 0 15 22 1 0 0 0 0 15 40 1 0 0 0 0 16 24 1 0 0 0 0 16 53 1 0 0 0 0 17 23 1 0 0 0 0 17 54 1 0 0 0 0 18 20 1 0 0 0 0 19 3 1 1 0 0 0 19 26 1 0 0 0 0 20 8 1 1 0 0 0 21 28 1 0 0 0 0 21 41 1 1 0 0 0 22 27 1 0 0 0 0 22 42 1 6 0 0 0 23 29 1 0 0 0 0 23 43 1 1 0 0 0 24 30 1 0 0 0 0 24 44 1 1 0 0 0 25 38 1 1 0 0 0 25 40 1 0 0 0 0 26 31 1 0 0 0 0 26 39 1 1 0 0 0 27 28 1 0 0 0 0 27 38 1 1 0 0 0 28 45 1 1 0 0 0 29 33 1 0 0 0 0 29 46 1 6 0 0 0 30 34 1 0 0 0 0 30 47 1 6 0 0 0 31 32 1 0 0 0 0 31 48 1 1 0 0 0 32 35 1 0 0 0 0 32 49 1 1 0 0 0 33 37 1 0 0 0 0 33 51 1 1 0 0 0 34 36 1 0 0 0 0 34 55 1 1 0 0 0 35 39 1 1 0 0 0 35 40 1 0 0 0 0 36 52 1 6 0 0 0 36 53 1 0 0 0 0 37 54 1 0 0 0 0 37 55 1 6 0 0 0 38 4 1 1 0 0 0 39 5 1 1 0 0 0 40 50 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	790.47
Volume:	780.911
LogP:	2.108
LogD:	2.515
LogS:	-2.884
# Rotatable Bonds:	12
TPSA:	248.45
# H-Bond Aceptor:	15
# H-Bond Donor:	10
# Rings:	6
# Heavy Atoms:	15

MedChem Properties

QED Drug-Likeness Score:	0.122
Synthetic Accessibility Score:	6.189
Fsp3:	1.0
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.905
MDCK Permeability:	0.0001074445026461035
Pgp-inhibitor:	0.622
Pgp-substrate:	0.996
Human Intestinal Absorption (HIA):	0.946
20% Bioavailability (F20%):	0.164
30% Bioavailability (F30%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.079
Plasma Protein Binding (PPB):	69.19283294677734%
Volume Distribution (VD):	0.064
Pgp-substrate:	10.18995475769043%

ADMET: Metabolism

CYP1A2-inhibitor:	0.001
CYP1A2-substrate:	0.929
CYP2C19-inhibitor:	0.001
CYP2C19-substrate:	0.266
CYP2C9-inhibitor:	0.001
CYP2C9-substrate:	0.008
CYP2D6-inhibitor:	0.001
CYP2D6-substrate:	0.064
CYP3A4-inhibitor:	0.027
CYP3A4-substrate:	0.019

ADMET: Excretion

Clearance (CL):	0.712
Half-life (T1/2):	0.585

ADMET: Toxicity

hERG Blockers:	0.494
Human Hepatotoxicity (H-HT):	0.171
Drug-inuced Liver Injury (DILI):	0.017
AMES Toxicity:	0.067
Rat Oral Acute Toxicity:	0.073
Maximum Recommended Daily Dose:	0.012
Skin Sensitization:	0.91
Carcinogencity:	0.019
Eye Corrosion:	0.003
Eye Irritation:	0.01
Respiratory Toxicity:	0.98

Download Data

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

Natural Product: NPC92196

Natural Product ID:	NPC92196
*Common Name:**	Halityloside A
IUPAC Name:	(3S,4R,5S,6S,8S,9R,10S,13R,14S,15S,16R,17R)-17-[(2R,5R)-5-[2-[(2R,3R,4S,5R)-3-[(2S,3R,4S,5R)-4,5-dihydroxy-3-methoxyoxan-2-yl]oxy-4,5-dihydroxyoxan-2-yl]oxyethyl]-6-methylheptan-2-yl]-10,13-dimethyl-1,2,3,4,5,6,7,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthrene-3,4,6,8,15,16-hexol
Synonyms:
Standard InCHIKey:	FCUKJXYRAXFXFI-JZZVNLILSA-N
Standard InCHI:	InChI=1S/C40H70O15/c1-18(2)20(11-14-52-36-34(30(47)24(44)16-53-36)55-37-33(51-6)29(46)23(43)17-54-37)8-7-19(3)26-31(48)32(49)35-39(26,5)13-10-25-38(4)12-9-21(41)28(45)27(38)22(42)15-40(25,35)50/h18-37,41-50H,7-17H2,1-6H3/t19-,20-,21+,22+,23-,24-,25-,26+,27+,28+,29+,30+,31-,32-,33-,34-,35-,36-,37+,38-,39-,40+/m1/s1
SMILES:	CC(C)[C@H](CC[C@@H](C)[C@H]1[C@H]([C@H]([C@@H]2[C@]1(C)CC[C@@H]1[C@@]3(C)CC[C@@H]([C@@H]([C@@H]3[C@H](C[C@@]21O)O)O)O)O)O)CCO[C@H]1[C@@H]([C@H]([C@@H](CO1)O)O)O[C@H]1[C@@H]([C@H]([C@@H](CO1)O)O)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL509736
PubChem CID:	21674185
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0002031] Stigmastanes and derivatives

*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
NPO33455	nardoa tuberculata	Species	Ophidiasteridae	Eukaryota	n.a.	Okinawan, Japan	n.a.	PMID[8377014]

☑ 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
LD50	1
MIC	1

Activity Type	# Activity
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT985	Organism	Cladosporium cucumerinum	Cladosporium cucumerinum	MIC	=	40.0	ug	PMID[529596]
NPT6256	Organism	Sphaerechinus granularis	Sphaerechinus granularis	LD50	=	1.0	10'-5M	PMID[529596]

☑ 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 NPC92196 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	596
0.1-0.2	5235
0.2-0.3	13114
0.3-0.4	11058
0.4-0.5	5495
0.5-0.6	3568
0.6-0.7	2017
0.7-0.8	1135
0.8-0.85	244
0.85-0.9	66
0.9-0.95	158
0.95-1	11

Similarity Score	Similarity Level	Natural Product ID
0.9886	High Similarity	NPC309866
0.9773	High Similarity	NPC277774
0.9659	High Similarity	NPC473830
0.9659	High Similarity	NPC36372
0.9659	High Similarity	NPC204881
0.9659	High Similarity	NPC293609
0.956	High Similarity	NPC477222
0.956	High Similarity	NPC477223
0.9545	High Similarity	NPC65550
0.9545	High Similarity	NPC223143
0.9545	High Similarity	NPC279329
0.9451	High Similarity	NPC473287
0.9444	High Similarity	NPC252253
0.9444	High Similarity	NPC3538
0.9444	High Similarity	NPC473774
0.9444	High Similarity	NPC45959
0.9444	High Similarity	NPC24960
0.9444	High Similarity	NPC477224
0.9444	High Similarity	NPC113500
0.9432	High Similarity	NPC473472
0.9432	High Similarity	NPC131466
0.9432	High Similarity	NPC102725
0.9348	High Similarity	NPC233649
0.9348	High Similarity	NPC470028
0.9341	High Similarity	NPC474399
0.9341	High Similarity	NPC477494
0.9333	High Similarity	NPC88962
0.9333	High Similarity	NPC149400
0.9333	High Similarity	NPC473726
0.9333	High Similarity	NPC311246
0.9333	High Similarity	NPC144790
0.9333	High Similarity	NPC137004
0.9333	High Similarity	NPC172838
0.9333	High Similarity	NPC167644
0.9318	High Similarity	NPC281004
0.9239	High Similarity	NPC304011
0.9239	High Similarity	NPC142264
0.9239	High Similarity	NPC476510
0.9239	High Similarity	NPC296936
0.9239	High Similarity	NPC139271
0.9239	High Similarity	NPC121453
0.9231	High Similarity	NPC179859
0.9231	High Similarity	NPC475436
0.9231	High Similarity	NPC222731
0.9231	High Similarity	NPC253268
0.9231	High Similarity	NPC473851
0.9231	High Similarity	NPC473503
0.9231	High Similarity	NPC475325
0.9231	High Similarity	NPC131693
0.9231	High Similarity	NPC174024
0.9231	High Similarity	NPC312678
0.9231	High Similarity	NPC294686
0.9231	High Similarity	NPC291547
0.9222	High Similarity	NPC5632
0.9222	High Similarity	NPC210759
0.9222	High Similarity	NPC307167
0.9222	High Similarity	NPC149966
0.9222	High Similarity	NPC229801
0.9205	High Similarity	NPC140446
0.9205	High Similarity	NPC43912
0.914	High Similarity	NPC274200
0.913	High Similarity	NPC469710
0.913	High Similarity	NPC473064
0.913	High Similarity	NPC473067
0.913	High Similarity	NPC94582
0.913	High Similarity	NPC57964
0.913	High Similarity	NPC473065
0.9121	High Similarity	NPC234352
0.9121	High Similarity	NPC476669
0.9121	High Similarity	NPC477547
0.9121	High Similarity	NPC48339
0.9121	High Similarity	NPC325828
0.9121	High Similarity	NPC249204
0.9121	High Similarity	NPC297348
0.9121	High Similarity	NPC141769
0.9121	High Similarity	NPC477451
0.9121	High Similarity	NPC250393
0.9121	High Similarity	NPC177834
0.9111	High Similarity	NPC473542
0.9053	High Similarity	NPC476838
0.9053	High Similarity	NPC476839
0.9053	High Similarity	NPC475574
0.9043	High Similarity	NPC473518
0.9043	High Similarity	NPC291548
0.9043	High Similarity	NPC473616
0.9043	High Similarity	NPC473638
0.9032	High Similarity	NPC473601
0.9032	High Similarity	NPC195297
0.9022	High Similarity	NPC471464
0.9022	High Similarity	NPC305418
0.9022	High Similarity	NPC264101
0.9022	High Similarity	NPC175
0.9022	High Similarity	NPC291203
0.9022	High Similarity	NPC217205
0.9011	High Similarity	NPC476668
0.9011	High Similarity	NPC473637
0.9	High Similarity	NPC20822
0.9	High Similarity	NPC82955
0.8977	High Similarity	NPC290612
0.8969	High Similarity	NPC475521
0.8958	High Similarity	NPC310138
0.8958	High Similarity	NPC114700
0.8958	High Similarity	NPC470029
0.8958	High Similarity	NPC134967
0.8936	High Similarity	NPC476112
0.8936	High Similarity	NPC475207
0.8936	High Similarity	NPC51520
0.8936	High Similarity	NPC83137
0.8936	High Similarity	NPC232611
0.8936	High Similarity	NPC470861
0.8936	High Similarity	NPC307534
0.8936	High Similarity	NPC115165
0.8936	High Similarity	NPC210157
0.8936	High Similarity	NPC470591
0.8936	High Similarity	NPC303069
0.8936	High Similarity	NPC470862
0.8925	High Similarity	NPC107188
0.8925	High Similarity	NPC473610
0.8925	High Similarity	NPC473727
0.8925	High Similarity	NPC206003
0.8925	High Similarity	NPC19400
0.8925	High Similarity	NPC475351
0.8925	High Similarity	NPC211354
0.8925	High Similarity	NPC6295
0.8925	High Similarity	NPC107962
0.8854	High Similarity	NPC472081
0.8854	High Similarity	NPC108227
0.8854	High Similarity	NPC477225
0.8854	High Similarity	NPC476512
0.883	High Similarity	NPC470864
0.883	High Similarity	NPC184617
0.883	High Similarity	NPC116756
0.883	High Similarity	NPC284104
0.883	High Similarity	NPC237071
0.883	High Similarity	NPC470866
0.883	High Similarity	NPC203434
0.883	High Similarity	NPC470865
0.883	High Similarity	NPC470863
0.883	High Similarity	NPC128572
0.883	High Similarity	NPC132080
0.883	High Similarity	NPC98018
0.883	High Similarity	NPC84111
0.883	High Similarity	NPC475625
0.883	High Similarity	NPC97700
0.883	High Similarity	NPC30856
0.883	High Similarity	NPC287483
0.883	High Similarity	NPC160426
0.883	High Similarity	NPC238796
0.883	High Similarity	NPC103616
0.883	High Similarity	NPC232037
0.883	High Similarity	NPC475643
0.8804	High Similarity	NPC59006
0.8778	High Similarity	NPC472396
0.8673	High Similarity	NPC476837
0.8673	High Similarity	NPC139181
0.8673	High Similarity	NPC97260
0.8667	High Similarity	NPC471240
0.866	High Similarity	NPC477172
0.8617	High Similarity	NPC191915
0.8617	High Similarity	NPC151214
0.8617	High Similarity	NPC30687
0.8614	High Similarity	NPC474573
0.8587	High Similarity	NPC228059
0.8557	High Similarity	NPC20028
0.8556	High Similarity	NPC232044
0.8556	High Similarity	NPC273290
0.8539	High Similarity	NPC241959
0.8515	High Similarity	NPC475634
0.8511	High Similarity	NPC224003
0.8511	High Similarity	NPC171741
0.8511	High Similarity	NPC470623
0.8511	High Similarity	NPC18724
0.8511	High Similarity	NPC323231
0.8478	Intermediate Similarity	NPC128475
0.8469	Intermediate Similarity	NPC31346
0.8444	Intermediate Similarity	NPC227260
0.8444	Intermediate Similarity	NPC474156
0.8438	Intermediate Similarity	NPC252056
0.8438	Intermediate Similarity	NPC472989
0.8438	Intermediate Similarity	NPC156377
0.8421	Intermediate Similarity	NPC471373
0.8421	Intermediate Similarity	NPC77717
0.8421	Intermediate Similarity	NPC148593
0.8421	Intermediate Similarity	NPC267238
0.8421	Intermediate Similarity	NPC253611
0.8416	Intermediate Similarity	NPC473469
0.84	Intermediate Similarity	NPC165033
0.84	Intermediate Similarity	NPC312774
0.84	Intermediate Similarity	NPC273879
0.8384	Intermediate Similarity	NPC80191
0.8384	Intermediate Similarity	NPC310031
0.837	Intermediate Similarity	NPC161928
0.837	Intermediate Similarity	NPC210658
0.8367	Intermediate Similarity	NPC41843
0.8367	Intermediate Similarity	NPC470030
0.8365	Intermediate Similarity	NPC475312
0.8365	Intermediate Similarity	NPC477489
0.8365	Intermediate Similarity	NPC477492
0.8351	Intermediate Similarity	NPC76486
0.8333	Intermediate Similarity	NPC471429

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 NPC92196 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	585
0.1-0.2	4679
0.2-0.3	2725
0.3-0.4	600
0.4-0.5	310
0.5-0.6	195
0.6-0.7	40
0.7-0.8	14
0.8-0.85	1
0.85-0.9	0
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9121	High Similarity	NPD8171	Discontinued
0.8218	Intermediate Similarity	NPD8170	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD6928	Phase 2
0.7611	Intermediate Similarity	NPD8378	Approved
0.7611	Intermediate Similarity	NPD8296	Approved
0.7611	Intermediate Similarity	NPD8335	Approved
0.7611	Intermediate Similarity	NPD8379	Approved
0.7611	Intermediate Similarity	NPD8380	Approved
0.7522	Intermediate Similarity	NPD8377	Approved
0.7522	Intermediate Similarity	NPD8294	Approved
0.7456	Intermediate Similarity	NPD8033	Approved
0.7455	Intermediate Similarity	NPD8133	Approved
0.7434	Intermediate Similarity	NPD7516	Approved
0.7345	Intermediate Similarity	NPD7328	Approved
0.7345	Intermediate Similarity	NPD7327	Approved
0.7273	Intermediate Similarity	NPD4267	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD1810	Approved
0.7143	Intermediate Similarity	NPD1811	Approved
0.7087	Intermediate Similarity	NPD7991	Discontinued
0.6937	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6864	Remote Similarity	NPD7503	Approved
0.6813	Remote Similarity	NPD7532	Clinical (unspecified phase)
0.6813	Remote Similarity	NPD2254	Approved
0.6813	Remote Similarity	NPD2686	Approved
0.6813	Remote Similarity	NPD2687	Approved
0.6777	Remote Similarity	NPD7507	Approved
0.6757	Remote Similarity	NPD6412	Phase 2
0.6748	Remote Similarity	NPD7319	Approved
0.6705	Remote Similarity	NPD371	Approved
0.6667	Remote Similarity	NPD3669	Approved
0.6667	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.663	Remote Similarity	NPD4787	Phase 1
0.6581	Remote Similarity	NPD6940	Discontinued
0.6549	Remote Similarity	NPD8174	Phase 2
0.6532	Remote Similarity	NPD7736	Approved
0.6495	Remote Similarity	NPD6115	Approved
0.6495	Remote Similarity	NPD6118	Approved
0.6495	Remote Similarity	NPD6697	Approved
0.6495	Remote Similarity	NPD6114	Approved
0.6393	Remote Similarity	NPD6370	Approved
0.6392	Remote Similarity	NPD6116	Phase 1
0.6341	Remote Similarity	NPD8328	Phase 3
0.6328	Remote Similarity	NPD8449	Approved
0.632	Remote Similarity	NPD8293	Discontinued
0.6289	Remote Similarity	NPD6117	Approved
0.6279	Remote Similarity	NPD8450	Suspended
0.623	Remote Similarity	NPD6054	Approved
0.623	Remote Similarity	NPD6059	Approved
0.62	Remote Similarity	NPD7525	Registered
0.6095	Remote Similarity	NPD7524	Approved
0.6087	Remote Similarity	NPD7625	Phase 1
0.6082	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6048	Remote Similarity	NPD6015	Approved
0.6048	Remote Similarity	NPD6016	Approved
0.6042	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6042	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6032	Remote Similarity	NPD7492	Approved
0.602	Remote Similarity	NPD3703	Phase 2
0.602	Remote Similarity	NPD3702	Approved
0.6019	Remote Similarity	NPD8034	Phase 2
0.6019	Remote Similarity	NPD8035	Phase 2
0.6018	Remote Similarity	NPD1700	Approved
0.6	Remote Similarity	NPD5988	Approved
0.5984	Remote Similarity	NPD6616	Approved
0.5983	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.5983	Remote Similarity	NPD6686	Approved
0.598	Remote Similarity	NPD1779	Approved
0.598	Remote Similarity	NPD1780	Approved
0.5968	Remote Similarity	NPD6319	Approved
0.5952	Remote Similarity	NPD6067	Discontinued
0.5938	Remote Similarity	NPD4244	Approved
0.5938	Remote Similarity	NPD4245	Approved
0.5938	Remote Similarity	NPD7078	Approved
0.5917	Remote Similarity	NPD6882	Approved
0.5917	Remote Similarity	NPD8297	Approved
0.5877	Remote Similarity	NPD4159	Approved
0.5862	Remote Similarity	NPD4057	Clinical (unspecified phase)
0.5862	Remote Similarity	NPD4056	Clinical (unspecified phase)
0.5854	Remote Similarity	NPD6009	Approved
0.5841	Remote Similarity	NPD7638	Approved
0.5833	Remote Similarity	NPD3698	Phase 2
0.5833	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.5833	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.5824	Remote Similarity	NPD6123	Approved
0.581	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.5798	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.5789	Remote Similarity	NPD7639	Approved
0.5789	Remote Similarity	NPD7640	Approved
0.5784	Remote Similarity	NPD7645	Phase 2
0.5769	Remote Similarity	NPD6033	Approved
0.5755	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.5738	Remote Similarity	NPD4632	Approved
0.5729	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.5729	Remote Similarity	NPD5360	Phase 3
0.5714	Remote Similarity	NPD5777	Approved
0.5714	Remote Similarity	NPD6695	Phase 3
0.5701	Remote Similarity	NPD8308	Discontinued
0.569	Remote Similarity	NPD7632	Discontinued
0.5678	Remote Similarity	NPD7128	Approved
0.5678	Remote Similarity	NPD6402	Approved
0.5678	Remote Similarity	NPD6675	Approved
0.5678	Remote Similarity	NPD5739	Approved
0.5669	Remote Similarity	NPD8515	Approved
0.5669	Remote Similarity	NPD8517	Approved
0.5669	Remote Similarity	NPD8513	Phase 3
0.5669	Remote Similarity	NPD8516	Approved
0.5667	Remote Similarity	NPD6372	Approved
0.5667	Remote Similarity	NPD6373	Approved
0.5648	Remote Similarity	NPD7750	Discontinued
0.5636	Remote Similarity	NPD6701	Clinical (unspecified phase)
0.5636	Remote Similarity	NPD6700	Approved
0.563	Remote Similarity	NPD7646	Clinical (unspecified phase)
0.562	Remote Similarity	NPD4634	Approved
0.562	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.5612	Remote Similarity	NPD4789	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