NPASS Compound

Structure

CID40170 OpenBabel06191715372D 34 37 0 0 1 0 0 0 0 0999 V2000 -3.4641 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 1.0000 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 5.3301 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8301 -2.6340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -2.5000 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 -4.3301 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -3.5000 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 1.7321 -3.0000 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 -2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.4641 -0.0000 0.0000 C 0 0 1 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 -0.8660 -1.5000 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 0.8660 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.4641 -3.0000 0.0000 C 0 0 2 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 -3.4641 1.0000 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 -0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7321 -3.0000 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 -1.7321 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -2.0000 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 8 1 0 0 0 0 4 26 1 0 0 0 0 5 26 1 0 0 0 0 8 15 1 0 0 0 0 9 11 1 0 0 0 0 9 21 1 0 0 0 0 10 12 1 0 0 0 0 10 22 1 0 0 0 0 11 27 1 0 0 0 0 12 28 1 0 0 0 0 13 17 2 0 0 0 0 13 19 1 0 0 0 0 14 18 1 0 0 0 0 14 20 1 0 0 0 0 15 2 1 1 0 0 0 15 23 1 0 0 0 0 16 3 1 6 0 0 0 16 17 1 0 0 0 0 16 23 1 0 0 0 0 17 24 1 0 0 0 0 18 19 1 0 0 0 0 18 25 2 0 0 0 0 19 29 2 0 0 0 0 20 27 1 1 0 0 0 20 28 1 0 0 0 0 21 26 1 1 0 0 0 21 33 1 0 0 0 0 22 27 1 1 0 0 0 22 33 1 0 0 0 0 23 30 2 0 0 0 0 24 25 1 0 0 0 0 24 31 2 0 0 0 0 25 34 1 0 0 0 0 26 32 1 0 0 0 0 27 6 1 1 0 0 0 28 7 1 1 0 0 0 28 34 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	472.28
Volume:	498.177
LogP:	4.253
LogD:	3.368
LogS:	-3.852
# Rotatable Bonds:	4
TPSA:	96.22
# H-Bond Aceptor:	6
# H-Bond Donor:	3
# Rings:	4
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.414
Synthetic Accessibility Score:	5.045
Fsp3:	0.679
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.731
MDCK Permeability:	2.1460002244566567e-05
Pgp-inhibitor:	0.88
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.01
20% Bioavailability (F20%):	0.221
30% Bioavailability (F30%):	0.172

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.239
Plasma Protein Binding (PPB):	99.51387786865234%
Volume Distribution (VD):	1.363
Pgp-substrate:	1.676689863204956%

ADMET: Metabolism

CYP1A2-inhibitor:	0.049
CYP1A2-substrate:	0.864
CYP2C19-inhibitor:	0.106
CYP2C19-substrate:	0.691
CYP2C9-inhibitor:	0.343
CYP2C9-substrate:	0.735
CYP2D6-inhibitor:	0.448
CYP2D6-substrate:	0.219
CYP3A4-inhibitor:	0.413
CYP3A4-substrate:	0.616

ADMET: Excretion

Clearance (CL):	2.467
Half-life (T1/2):	0.375

ADMET: Toxicity

hERG Blockers:	0.051
Human Hepatotoxicity (H-HT):	0.616
Drug-inuced Liver Injury (DILI):	0.031
AMES Toxicity:	0.011
Rat Oral Acute Toxicity:	0.644
Maximum Recommended Daily Dose:	0.919
Skin Sensitization:	0.733
Carcinogencity:	0.02
Eye Corrosion:	0.003
Eye Irritation:	0.243
Respiratory Toxicity:	0.195

Download Data

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

Natural Product: NPC40170

Natural Product ID:	NPC40170
*Common Name:**	Cochlioquinone B
IUPAC Name:	(3R,4aR,6aR,12aR,12bR)-3-(2-hydroxypropan-2-yl)-6a,12b-dimethyl-9-[(2S,4S)-4-methyl-3-oxohexan-2-yl]-1,2,3,4a,5,6,12,12a-octahydropyrano[3,2-a]xanthene-8,11-dione
Synonyms:
Standard InCHIKey:	NTPNSKLZWVYKGK-WWURSIHSSA-N
Standard InCHI:	InChI=1S/C28H40O6/c1-8-15(2)23(30)16(3)17-13-19(29)18-14-20-27(6)11-9-21(26(4,5)32)33-22(27)10-12-28(20,7)34-25(18)24(17)31/h13,15-16,20-22,32H,8-12,14H2,1-7H3/t15-,16-,20+,21+,22+,27+,28+/m0/s1
SMILES:	CC[C@@H](C(=O)[C@H](C1=CC(=O)C2=C(C1=O)O[C@]1([C@H](C2)[C@@]2(C)CC[C@@H](O[C@@H]2CC1)C(O)(C)C)C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2288169
PubChem CID:	182083
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0002012] Oxanes

*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
NPO20405	Geodia exigua	Species	Geodiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[12372496]
NPO18989	Aplysia depilans	Species	Aplysiidae	Eukaryota	n.a.	Skyros Island (GPS coordinates 3887' N, 2457' E), in the North Sporades complex of the Aegean Sea, Greece	2011-AUG	PMID[25814031]
NPO23429	Lycium barbarum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31397570]
NPO23429	Lycium barbarum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO23429	Lycium barbarum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23429	Lycium barbarum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO23429	Lycium barbarum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO23919	Centaurea nigra	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23429	Lycium barbarum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15914	Savalia savaglia	Species	Parazoanthidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23811	Morella esculenta	Species	Myricaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20405	Geodia exigua	Species	Geodiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23317	Annona cristalensis	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25386	Arthrospira platensis	Species	Microcoleaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO18989	Aplysia depilans	Species	Aplysiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ 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	7
MIC	3
Others	3

Activity Type	# Activity
Cell Line	2
Individual Protein	1
Organism	3
Others	7

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2783	Individual Protein	Cytochrome b-245 light chain	Bos taurus	IC50	=	83.0	nM	PMID[507150]
NPT405	Cell Line	NCI-H226	Homo sapiens	Inhibition	<	50.0	%	PMID[507152]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	Inhibition	<	50.0	%	PMID[507152]
NPT2	Others	Unspecified		IC50	=	3000.0	nM	PMID[507150]
NPT2	Others	Unspecified		IC50	>	3600.0	nM	PMID[507150]
NPT2	Others	Unspecified		IC50	=	370.0	nM	PMID[507150]
NPT35	Others	n.a.		log K	=	0.437	n.a.	PMID[507151]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	=	26000.0	nM	PMID[507152]
NPT1359	Organism	Clostridium perfringens	Clostridium perfringens	MIC	=	26000.0	nM	PMID[507152]
NPT26640	ORGANISM	Pseudomonas viridiflava	Pseudomonas viridiflava	MIC	=	26000.0	nM	PMID[507152]

☑ 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 NPC40170 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	228
0.1-0.2	1373
0.2-0.3	4371
0.3-0.4	8534
0.4-0.5	13810
0.5-0.6	8019
0.6-0.7	5220
0.7-0.8	1098
0.8-0.85	28
0.85-0.9	9
0.9-0.95	4
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.8544	High Similarity	NPC179208
0.8485	Intermediate Similarity	NPC212812
0.844	Intermediate Similarity	NPC247069
0.8367	Intermediate Similarity	NPC223093
0.8318	Intermediate Similarity	NPC27814
0.8283	Intermediate Similarity	NPC248913
0.8257	Intermediate Similarity	NPC90769
0.8182	Intermediate Similarity	NPC472325
0.8119	Intermediate Similarity	NPC472976
0.8119	Intermediate Similarity	NPC472977
0.8119	Intermediate Similarity	NPC293086
0.8091	Intermediate Similarity	NPC193948
0.8077	Intermediate Similarity	NPC472972
0.8056	Intermediate Similarity	NPC293850
0.8053	Intermediate Similarity	NPC176005
0.8036	Intermediate Similarity	NPC328374
0.8036	Intermediate Similarity	NPC235539
0.8036	Intermediate Similarity	NPC152199
0.8036	Intermediate Similarity	NPC251236
0.8036	Intermediate Similarity	NPC96312
0.8036	Intermediate Similarity	NPC40632
0.8036	Intermediate Similarity	NPC134869
0.8019	Intermediate Similarity	NPC194323
0.8018	Intermediate Similarity	NPC208998
0.8018	Intermediate Similarity	NPC7921
0.8	Intermediate Similarity	NPC146945
0.8	Intermediate Similarity	NPC474209
0.8	Intermediate Similarity	NPC171888
0.8	Intermediate Similarity	NPC475823
0.7982	Intermediate Similarity	NPC41405
0.798	Intermediate Similarity	NPC475001
0.798	Intermediate Similarity	NPC185059
0.7961	Intermediate Similarity	NPC472733
0.7961	Intermediate Similarity	NPC472734
0.7946	Intermediate Similarity	NPC473798
0.7946	Intermediate Similarity	NPC18547
0.7946	Intermediate Similarity	NPC474906
0.7944	Intermediate Similarity	NPC137657
0.7941	Intermediate Similarity	NPC23170
0.7941	Intermediate Similarity	NPC477439
0.7921	Intermediate Similarity	NPC99380
0.7913	Intermediate Similarity	NPC478051
0.7905	Intermediate Similarity	NPC104861
0.7905	Intermediate Similarity	NPC46761
0.7895	Intermediate Similarity	NPC297179
0.789	Intermediate Similarity	NPC154608
0.789	Intermediate Similarity	NPC277017
0.789	Intermediate Similarity	NPC192813
0.7885	Intermediate Similarity	NPC473456
0.7885	Intermediate Similarity	NPC472731
0.7885	Intermediate Similarity	NPC472732
0.7879	Intermediate Similarity	NPC472324
0.7864	Intermediate Similarity	NPC473170
0.7864	Intermediate Similarity	NPC477438
0.7864	Intermediate Similarity	NPC477437
0.7857	Intermediate Similarity	NPC132228
0.7857	Intermediate Similarity	NPC6185
0.7857	Intermediate Similarity	NPC194100
0.7857	Intermediate Similarity	NPC198539
0.7857	Intermediate Similarity	NPC263997
0.7857	Intermediate Similarity	NPC49451
0.7857	Intermediate Similarity	NPC241512
0.7857	Intermediate Similarity	NPC8518
0.7851	Intermediate Similarity	NPC476193
0.7843	Intermediate Similarity	NPC477435
0.7843	Intermediate Similarity	NPC477436
0.7838	Intermediate Similarity	NPC201992
0.783	Intermediate Similarity	NPC472637
0.7826	Intermediate Similarity	NPC470777
0.7826	Intermediate Similarity	NPC279143
0.7818	Intermediate Similarity	NPC87335
0.7818	Intermediate Similarity	NPC20192
0.781	Intermediate Similarity	NPC472729
0.781	Intermediate Similarity	NPC177680
0.781	Intermediate Similarity	NPC153776
0.781	Intermediate Similarity	NPC472730
0.7807	Intermediate Similarity	NPC470854
0.7807	Intermediate Similarity	NPC97908
0.7807	Intermediate Similarity	NPC122033
0.7807	Intermediate Similarity	NPC287343
0.7807	Intermediate Similarity	NPC474654
0.78	Intermediate Similarity	NPC158778
0.7798	Intermediate Similarity	NPC202524
0.7798	Intermediate Similarity	NPC144854
0.7798	Intermediate Similarity	NPC3316
0.7778	Intermediate Similarity	NPC149124
0.7778	Intermediate Similarity	NPC75531
0.7768	Intermediate Similarity	NPC289312
0.7768	Intermediate Similarity	NPC11252
0.7759	Intermediate Similarity	NPC107338
0.7759	Intermediate Similarity	NPC109607
0.7757	Intermediate Similarity	NPC163249
0.7748	Intermediate Similarity	NPC239097
0.7748	Intermediate Similarity	NPC210005
0.7745	Intermediate Similarity	NPC472978
0.7745	Intermediate Similarity	NPC472975
0.7739	Intermediate Similarity	NPC17772
0.7739	Intermediate Similarity	NPC204552
0.7739	Intermediate Similarity	NPC188667
0.7739	Intermediate Similarity	NPC251310
0.7736	Intermediate Similarity	NPC472728
0.7736	Intermediate Similarity	NPC472727
0.7723	Intermediate Similarity	NPC472973
0.7714	Intermediate Similarity	NPC170131
0.7714	Intermediate Similarity	NPC474977
0.7714	Intermediate Similarity	NPC27105
0.7706	Intermediate Similarity	NPC102352
0.7706	Intermediate Similarity	NPC478052
0.7699	Intermediate Similarity	NPC477266
0.7699	Intermediate Similarity	NPC51978
0.7699	Intermediate Similarity	NPC255017
0.7692	Intermediate Similarity	NPC279313
0.7692	Intermediate Similarity	NPC275675
0.7692	Intermediate Similarity	NPC134067
0.7685	Intermediate Similarity	NPC264048
0.7685	Intermediate Similarity	NPC131366
0.7685	Intermediate Similarity	NPC275583
0.7685	Intermediate Similarity	NPC239716
0.7685	Intermediate Similarity	NPC470839
0.7677	Intermediate Similarity	NPC133652
0.7677	Intermediate Similarity	NPC79573
0.7672	Intermediate Similarity	NPC475775
0.7672	Intermediate Similarity	NPC476529
0.7672	Intermediate Similarity	NPC469488
0.7672	Intermediate Similarity	NPC127530
0.7672	Intermediate Similarity	NPC473920
0.767	Intermediate Similarity	NPC61275
0.7664	Intermediate Similarity	NPC470184
0.7652	Intermediate Similarity	NPC309433
0.7647	Intermediate Similarity	NPC470922
0.7647	Intermediate Similarity	NPC469464
0.7647	Intermediate Similarity	NPC24651
0.7647	Intermediate Similarity	NPC475194
0.7642	Intermediate Similarity	NPC471331
0.7642	Intermediate Similarity	NPC203388
0.7642	Intermediate Similarity	NPC471330
0.7642	Intermediate Similarity	NPC99657
0.7642	Intermediate Similarity	NPC472687
0.7636	Intermediate Similarity	NPC144459
0.7636	Intermediate Similarity	NPC44063
0.7619	Intermediate Similarity	NPC91439
0.7619	Intermediate Similarity	NPC473158
0.7619	Intermediate Similarity	NPC21681
0.7619	Intermediate Similarity	NPC5532
0.7619	Intermediate Similarity	NPC61369
0.7619	Intermediate Similarity	NPC469545
0.7619	Intermediate Similarity	NPC472675
0.7619	Intermediate Similarity	NPC471463
0.7615	Intermediate Similarity	NPC65523
0.7615	Intermediate Similarity	NPC118911
0.7615	Intermediate Similarity	NPC284865
0.7611	Intermediate Similarity	NPC474516
0.7607	Intermediate Similarity	NPC112038
0.7603	Intermediate Similarity	NPC477712
0.7603	Intermediate Similarity	NPC477713
0.7596	Intermediate Similarity	NPC160413
0.7596	Intermediate Similarity	NPC196227
0.7596	Intermediate Similarity	NPC474328
0.7596	Intermediate Similarity	NPC478089
0.7596	Intermediate Similarity	NPC103527
0.7593	Intermediate Similarity	NPC478176
0.7593	Intermediate Similarity	NPC473424
0.7593	Intermediate Similarity	NPC80781
0.7576	Intermediate Similarity	NPC251170
0.7573	Intermediate Similarity	NPC185936
0.7573	Intermediate Similarity	NPC168027
0.7573	Intermediate Similarity	NPC146852
0.7573	Intermediate Similarity	NPC155304
0.757	Intermediate Similarity	NPC144956
0.757	Intermediate Similarity	NPC471727
0.7568	Intermediate Similarity	NPC272576
0.7565	Intermediate Similarity	NPC474046
0.7565	Intermediate Similarity	NPC478216
0.7565	Intermediate Similarity	NPC474734
0.7565	Intermediate Similarity	NPC173686
0.7565	Intermediate Similarity	NPC259306
0.7565	Intermediate Similarity	NPC16081
0.7565	Intermediate Similarity	NPC176840
0.7565	Intermediate Similarity	NPC190286
0.7565	Intermediate Similarity	NPC470628
0.7565	Intermediate Similarity	NPC207217
0.7563	Intermediate Similarity	NPC18945
0.7563	Intermediate Similarity	NPC105926
0.7563	Intermediate Similarity	NPC265557
0.7563	Intermediate Similarity	NPC227397
0.7563	Intermediate Similarity	NPC91693
0.7551	Intermediate Similarity	NPC103486
0.7551	Intermediate Similarity	NPC48362
0.7547	Intermediate Similarity	NPC18509
0.7547	Intermediate Similarity	NPC285513
0.7547	Intermediate Similarity	NPC254496
0.7547	Intermediate Similarity	NPC273269
0.7547	Intermediate Similarity	NPC470834
0.7547	Intermediate Similarity	NPC272451
0.7547	Intermediate Similarity	NPC20066
0.7545	Intermediate Similarity	NPC292588
0.7545	Intermediate Similarity	NPC471333
0.7545	Intermediate Similarity	NPC471332
0.7545	Intermediate Similarity	NPC85529
0.7545	Intermediate Similarity	NPC60681

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 NPC40170 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	206
0.1-0.2	1657
0.2-0.3	3758
0.3-0.4	2302
0.4-0.5	792
0.5-0.6	223
0.6-0.7	112
0.7-0.8	100
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
0.7768	Intermediate Similarity	NPD8297	Approved
0.7727	Intermediate Similarity	NPD6899	Approved
0.7727	Intermediate Similarity	NPD6881	Approved
0.7706	Intermediate Similarity	NPD5739	Approved
0.7706	Intermediate Similarity	NPD7128	Approved
0.7706	Intermediate Similarity	NPD6675	Approved
0.7706	Intermediate Similarity	NPD6402	Approved
0.7679	Intermediate Similarity	NPD6650	Approved
0.7679	Intermediate Similarity	NPD6649	Approved
0.7658	Intermediate Similarity	NPD6373	Approved
0.7658	Intermediate Similarity	NPD6372	Approved
0.7636	Intermediate Similarity	NPD5697	Approved
0.7589	Intermediate Similarity	NPD6883	Approved
0.7589	Intermediate Similarity	NPD7102	Approved
0.7589	Intermediate Similarity	NPD7290	Approved
0.757	Intermediate Similarity	NPD4696	Approved
0.757	Intermediate Similarity	NPD5285	Approved
0.757	Intermediate Similarity	NPD5286	Approved
0.7568	Intermediate Similarity	NPD6011	Approved
0.7568	Intermediate Similarity	NPD7320	Approved
0.7547	Intermediate Similarity	NPD7902	Approved
0.7547	Intermediate Similarity	NPD4755	Approved
0.7526	Intermediate Similarity	NPD4695	Discontinued
0.7522	Intermediate Similarity	NPD6617	Approved
0.7522	Intermediate Similarity	NPD8130	Phase 1
0.7522	Intermediate Similarity	NPD6869	Approved
0.7522	Intermediate Similarity	NPD6847	Approved
0.75	Intermediate Similarity	NPD5223	Approved
0.75	Intermediate Similarity	NPD6013	Approved
0.75	Intermediate Similarity	NPD6012	Approved
0.75	Intermediate Similarity	NPD6014	Approved
0.7477	Intermediate Similarity	NPD5701	Approved
0.7456	Intermediate Similarity	NPD6882	Approved
0.7453	Intermediate Similarity	NPD4697	Phase 3
0.7453	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7453	Intermediate Similarity	NPD5222	Approved
0.7453	Intermediate Similarity	NPD5221	Approved
0.7431	Intermediate Similarity	NPD5224	Approved
0.7431	Intermediate Similarity	NPD5226	Approved
0.7431	Intermediate Similarity	NPD4633	Approved
0.7431	Intermediate Similarity	NPD5211	Phase 2
0.7431	Intermediate Similarity	NPD5225	Approved
0.7429	Intermediate Similarity	NPD7748	Approved
0.7407	Intermediate Similarity	NPD4700	Approved
0.7404	Intermediate Similarity	NPD6079	Approved
0.7391	Intermediate Similarity	NPD4632	Approved
0.7383	Intermediate Similarity	NPD5173	Approved
0.7379	Intermediate Similarity	NPD5328	Approved
0.7368	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7364	Intermediate Similarity	NPD5175	Approved
0.7364	Intermediate Similarity	NPD5174	Approved
0.7353	Intermediate Similarity	NPD3573	Approved
0.7311	Intermediate Similarity	NPD6054	Approved
0.7311	Intermediate Similarity	NPD6319	Approved
0.7297	Intermediate Similarity	NPD5141	Approved
0.7281	Intermediate Similarity	NPD4634	Approved
0.7273	Intermediate Similarity	NPD8328	Phase 3
0.7264	Intermediate Similarity	NPD7900	Approved
0.7264	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7238	Intermediate Similarity	NPD7515	Phase 2
0.7207	Intermediate Similarity	NPD4754	Approved
0.7203	Intermediate Similarity	NPD6009	Approved
0.7203	Intermediate Similarity	NPD7115	Discovery
0.719	Intermediate Similarity	NPD6370	Approved
0.717	Intermediate Similarity	NPD6399	Phase 3
0.7167	Intermediate Similarity	NPD6059	Approved
0.7143	Intermediate Similarity	NPD6335	Approved
0.7131	Intermediate Similarity	NPD7604	Phase 2
0.7119	Intermediate Similarity	NPD6274	Approved
0.7107	Intermediate Similarity	NPD5983	Phase 2
0.7107	Intermediate Similarity	NPD6016	Approved
0.7107	Intermediate Similarity	NPD6015	Approved
0.7105	Intermediate Similarity	NPD4730	Approved
0.7105	Intermediate Similarity	NPD4729	Approved
0.7105	Intermediate Similarity	NPD5128	Approved
0.7087	Intermediate Similarity	NPD3618	Phase 1
0.7083	Intermediate Similarity	NPD7101	Approved
0.7083	Intermediate Similarity	NPD7100	Approved
0.708	Intermediate Similarity	NPD4767	Approved
0.708	Intermediate Similarity	NPD4768	Approved
0.7073	Intermediate Similarity	NPD7492	Approved
0.7064	Intermediate Similarity	NPD6084	Phase 2
0.7064	Intermediate Similarity	NPD6083	Phase 2
0.7059	Intermediate Similarity	NPD6317	Approved
0.7049	Intermediate Similarity	NPD5988	Approved
0.704	Intermediate Similarity	NPD7736	Approved
0.7037	Intermediate Similarity	NPD5695	Phase 3
0.7018	Intermediate Similarity	NPD6412	Phase 2
0.7016	Intermediate Similarity	NPD6616	Approved
0.7016	Intermediate Similarity	NPD6336	Discontinued
0.7009	Intermediate Similarity	NPD4202	Approved
0.7	Intermediate Similarity	NPD6314	Approved
0.7	Intermediate Similarity	NPD6313	Approved
0.6983	Remote Similarity	NPD5169	Approved
0.6983	Remote Similarity	NPD5247	Approved
0.6983	Remote Similarity	NPD5250	Approved
0.6983	Remote Similarity	NPD5135	Approved
0.6983	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6983	Remote Similarity	NPD5251	Approved
0.6983	Remote Similarity	NPD5248	Approved
0.6983	Remote Similarity	NPD5249	Phase 3
0.6975	Remote Similarity	NPD6868	Approved
0.696	Remote Similarity	NPD7078	Approved
0.6957	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6952	Remote Similarity	NPD6672	Approved
0.6952	Remote Similarity	NPD5737	Approved
0.6944	Remote Similarity	NPD5282	Discontinued
0.6923	Remote Similarity	NPD5127	Approved
0.6923	Remote Similarity	NPD5215	Approved
0.6923	Remote Similarity	NPD5216	Approved
0.6923	Remote Similarity	NPD5217	Approved
0.6923	Remote Similarity	NPD5279	Phase 3
0.6917	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6916	Remote Similarity	NPD6411	Approved
0.6893	Remote Similarity	NPD4786	Approved
0.6887	Remote Similarity	NPD4753	Phase 2
0.6887	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6863	Remote Similarity	NPD3667	Approved
0.6847	Remote Similarity	NPD5696	Approved
0.6829	Remote Similarity	NPD6908	Approved
0.6829	Remote Similarity	NPD6909	Approved
0.6827	Remote Similarity	NPD5329	Approved
0.6825	Remote Similarity	NPD8293	Discontinued
0.681	Remote Similarity	NPD5168	Approved
0.6783	Remote Similarity	NPD6008	Approved
0.6772	Remote Similarity	NPD6033	Approved
0.6762	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6762	Remote Similarity	NPD5690	Phase 2
0.6752	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.675	Remote Similarity	NPD5167	Approved
0.6731	Remote Similarity	NPD4197	Approved
0.6731	Remote Similarity	NPD3666	Approved
0.6731	Remote Similarity	NPD3665	Phase 1
0.6731	Remote Similarity	NPD3133	Approved
0.6729	Remote Similarity	NPD6673	Approved
0.6729	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6729	Remote Similarity	NPD6904	Approved
0.6729	Remote Similarity	NPD6080	Approved
0.6729	Remote Similarity	NPD6101	Approved
0.6727	Remote Similarity	NPD5210	Approved
0.6727	Remote Similarity	NPD4629	Approved
0.6696	Remote Similarity	NPD4225	Approved
0.6694	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6686	Approved
0.6636	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6634	Remote Similarity	NPD3617	Approved
0.6614	Remote Similarity	NPD7507	Approved
0.661	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6606	Remote Similarity	NPD6050	Approved
0.6606	Remote Similarity	NPD8035	Phase 2
0.6606	Remote Similarity	NPD8034	Phase 2
0.6604	Remote Similarity	NPD7334	Approved
0.6604	Remote Similarity	NPD6409	Approved
0.6604	Remote Similarity	NPD5330	Approved
0.6604	Remote Similarity	NPD4694	Approved
0.6604	Remote Similarity	NPD7146	Approved
0.6604	Remote Similarity	NPD7521	Approved
0.6604	Remote Similarity	NPD6684	Approved
0.6604	Remote Similarity	NPD5280	Approved
0.6571	Remote Similarity	NPD3668	Phase 3
0.6555	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6538	Remote Similarity	NPD4221	Approved
0.6538	Remote Similarity	NPD4223	Phase 3
0.6514	Remote Similarity	NPD5692	Phase 3
0.6489	Remote Similarity	NPD7260	Phase 2
0.6481	Remote Similarity	NPD6903	Approved
0.6476	Remote Similarity	NPD6110	Phase 1
0.6462	Remote Similarity	NPD7319	Approved
0.6455	Remote Similarity	NPD5694	Approved
0.6455	Remote Similarity	NPD5693	Phase 1
0.6449	Remote Similarity	NPD6098	Approved
0.6446	Remote Similarity	NPD6053	Discontinued
0.6429	Remote Similarity	NPD7503	Approved
0.6429	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6408	Remote Similarity	NPD7645	Phase 2
0.6404	Remote Similarity	NPD7638	Approved
0.6355	Remote Similarity	NPD1696	Phase 3
0.6354	Remote Similarity	NPD7331	Phase 2
0.6348	Remote Similarity	NPD7639	Approved
0.6348	Remote Similarity	NPD7640	Approved
0.6346	Remote Similarity	NPD7525	Registered
0.6321	Remote Similarity	NPD4788	Approved
0.6306	Remote Similarity	NPD5281	Approved
0.6306	Remote Similarity	NPD5284	Approved
0.6303	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6299	Remote Similarity	NPD6921	Approved
0.6296	Remote Similarity	NPD4623	Approved
0.6296	Remote Similarity	NPD4519	Discontinued
0.6296	Remote Similarity	NPD4688	Approved
0.6296	Remote Similarity	NPD5205	Approved
0.6296	Remote Similarity	NPD4138	Approved
0.6296	Remote Similarity	NPD4689	Approved
0.6296	Remote Similarity	NPD4690	Approved
0.6296	Remote Similarity	NPD4693	Phase 3
0.6293	Remote Similarity	NPD5344	Discontinued
0.625	Remote Similarity	NPD7341	Phase 2
0.625	Remote Similarity	NPD5778	Approved
0.625	Remote Similarity	NPD5779	Approved
0.6228	Remote Similarity	NPD7614	Phase 1

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