NPASS Compound

Structure

CID177668 OpenBabel06191715552D 38 41 0 0 1 0 0 0 0 0999 V2000 7.3751 -3.1681 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0156 -4.2752 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 5.9131 -1.3554 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3257 -0.0592 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9197 -0.8642 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8588 -0.2292 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2931 -1.6668 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7663 -0.0715 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 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1563 -3.0596 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7395 -2.1224 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 5.1204 -3.4410 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 4.1808 -1.8364 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5261 -2.6397 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.6702 -3.3367 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 6.3078 -0.5631 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 6.7734 -1.5639 0.0000 C 0 0 1 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 4.5666 -3.3611 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.5116 -1.0933 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.6808 -2.7024 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.2412 -0.2649 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 4.0687 -3.1057 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.2628 -4.3138 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.7459 0.6039 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4720 -3.9081 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.6241 -1.0246 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.7026 -2.4945 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.8073 -0.6182 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 19 2 0 0 0 0 3 20 1 0 0 0 0 4 6 2 0 0 0 0 4 8 1 0 0 0 0 5 7 1 0 0 0 0 5 9 2 0 0 0 0 7 21 1 0 0 0 0 9 28 1 0 0 0 0 10 11 2 0 0 0 0 12 18 1 0 0 0 0 12 19 1 0 0 0 0 13 18 1 0 0 0 0 13 22 1 0 0 0 0 14 20 1 0 0 0 0 14 23 1 0 0 0 0 15 19 1 0 0 0 0 15 24 1 0 0 0 0 16 20 2 0 0 0 0 16 29 1 0 0 0 0 18 1 1 1 0 0 0 21 6 1 6 0 0 0 21 35 1 0 0 0 0 22 8 1 1 0 0 0 22 35 1 0 0 0 0 23 10 1 6 0 0 0 23 36 1 0 0 0 0 24 30 1 0 0 0 0 24 31 1 6 0 0 0 25 11 1 1 0 0 0 25 26 1 0 0 0 0 25 37 1 0 0 0 0 26 17 1 1 0 0 0 26 38 1 0 0 0 0 27 17 1 6 0 0 0 27 30 1 0 0 0 0 27 37 1 0 0 0 0 28 32 2 0 0 0 0 28 38 1 0 0 0 0 29 33 2 0 0 0 0 29 36 1 0 0 0 0 30 34 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	528.27
Volume:	545.077
LogP:	3.839
LogD:	2.875
LogS:	-4.549
# Rotatable Bonds:	2
TPSA:	111.52
# H-Bond Aceptor:	8
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.413
Synthetic Accessibility Score:	7.328
Fsp3:	0.6
Lipinski Rule-of-5:	Accepted
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:	-5.192
MDCK Permeability:	6.562481576111168e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.014
Human Intestinal Absorption (HIA):	0.849
20% Bioavailability (F20%):	0.423
30% Bioavailability (F30%):	0.995

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.086
Plasma Protein Binding (PPB):	72.5372543334961%
Volume Distribution (VD):	1.2
Pgp-substrate:	9.398699760437012%

ADMET: Metabolism

CYP1A2-inhibitor:	0.015
CYP1A2-substrate:	0.051
CYP2C19-inhibitor:	0.036
CYP2C19-substrate:	0.067
CYP2C9-inhibitor:	0.175
CYP2C9-substrate:	0.066
CYP2D6-inhibitor:	0.008
CYP2D6-substrate:	0.079
CYP3A4-inhibitor:	0.723
CYP3A4-substrate:	0.218

ADMET: Excretion

Clearance (CL):	2.458
Half-life (T1/2):	0.481

ADMET: Toxicity

hERG Blockers:	0.024
Human Hepatotoxicity (H-HT):	0.935
Drug-inuced Liver Injury (DILI):	0.942
AMES Toxicity:	0.949
Rat Oral Acute Toxicity:	0.295
Maximum Recommended Daily Dose:	0.992
Skin Sensitization:	0.292
Carcinogencity:	0.179
Eye Corrosion:	0.003
Eye Irritation:	0.009
Respiratory Toxicity:	0.759

Download Data

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

Natural Product: NPC177668

Natural Product ID:	NPC177668
*Common Name:**	Fiijianolide D
IUPAC Name:	n.a.
Synonyms:	Fiijianolide D; Fijianolide D
Standard InCHIKey:	CVVBJPYJIWDRMQ-FVRSRKCVSA-N
Standard InCHI:	InChI=1S/C30H40O8/c1-18-12-19(2)15-24(31)30(34)27-17-26(25(37-27)11-10-23-14-20(3)16-29(33)36-23)38-28(32)9-5-7-21-6-4-8-22(13-18)35-21/h4-6,9-11,16,18,21-27,30-31,34H,2,7-8,12-15,17H2,1,3H3/b9-5-,11-10+/t18-,21-,22-,23+,24-,25-,26-,27+,30-/m0/s1
SMILES:	O=C1/C=CC[C@@H]2C=CC[C@H](O2)C[C@@H](C)CC(=C)C[C@@H]([C@@H]([C@H]2C[C@H](O1)[C@H](/C=C/[C@@H]1CC(=CC(=O)O1)C)O2)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL388441
PubChem CID:	16756958
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000147] Macrolides and analogues

*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
NPO19376	Cacospongia mycofijiensis	Species	Thorectidae	Eukaryota	n.a.	n.a.	n.a.	PMID[18942825]
NPO19376	Cacospongia mycofijiensis	Species	Thorectidae	Eukaryota	n.a.	Tongan	n.a.	PMID[19877653]
NPO19376	Cacospongia mycofijiensis	Species	Thorectidae	Eukaryota	n.a.	n.a.	n.a.	PMID[22129061]
NPO19376	Cacospongia mycofijiensis	Species	Thorectidae	Eukaryota	n.a.	n.a.	n.a.	PMID[30371079]
NPO19376	Cacospongia mycofijiensis	Species	Thorectidae	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
Others	4

Activity Type	# Activity
Cell Line	7
NON-MOLECULAR	3
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT400	Cell Line	MDA-MB-435	Homo sapiens	IC50	=	21400.0	nM	PMID[524850]
NPT393	Cell Line	HCT-116	Homo sapiens	IC50	=	1900.0	nM	PMID[524850]
NPT137	Cell Line	L1210	Mus musculus	Activity	=	0.0	Zone units	PMID[524850]
NPT730	Cell Line	MC-38	Mus musculus	Activity	=	150.0	Zone units	PMID[524850]
NPT139	Cell Line	HT-29	Homo sapiens	IC50	>	2.5	ug.mL-1	PMID[524851]
NPT400	Cell Line	MDA-MB-435	Homo sapiens	IC50	>	2.5	ug.mL-1	PMID[524851]
NPT466	Cell Line	U-937	Homo sapiens	IC50	>	2.5	ug.mL-1	PMID[524851]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	0.0	Zone units	PMID[524850]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	2.5	ug.mL-1	PMID[524851]
NPT471	Organism	Trypanosoma brucei brucei	Trypanosoma brucei brucei	IC50	=	1.4	ug.mL-1	PMID[524851]

☑ 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 NPC177668 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	180
0.1-0.2	1045
0.2-0.3	4225
0.3-0.4	9368
0.4-0.5	14190
0.5-0.6	8087
0.6-0.7	4308
0.7-0.8	1267
0.8-0.85	23
0.85-0.9	1
0.9-0.95	0
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9881	High Similarity	NPC133450
0.9655	High Similarity	NPC256368
0.931	High Similarity	NPC3952
0.8913	High Similarity	NPC475332
0.869	High Similarity	NPC139712
0.8471	Intermediate Similarity	NPC180725
0.8452	Intermediate Similarity	NPC474026
0.8427	Intermediate Similarity	NPC311163
0.8372	Intermediate Similarity	NPC133226
0.8372	Intermediate Similarity	NPC470147
0.837	Intermediate Similarity	NPC114172
0.837	Intermediate Similarity	NPC206679
0.837	Intermediate Similarity	NPC471324
0.8353	Intermediate Similarity	NPC248775
0.8316	Intermediate Similarity	NPC120299
0.8315	Intermediate Similarity	NPC471494
0.8298	Intermediate Similarity	NPC36954
0.8295	Intermediate Similarity	NPC44261
0.828	Intermediate Similarity	NPC109406
0.828	Intermediate Similarity	NPC159092
0.828	Intermediate Similarity	NPC472196
0.828	Intermediate Similarity	NPC238090
0.828	Intermediate Similarity	NPC472195
0.828	Intermediate Similarity	NPC476300
0.8276	Intermediate Similarity	NPC8538
0.8276	Intermediate Similarity	NPC184208
0.8256	Intermediate Similarity	NPC470148
0.8256	Intermediate Similarity	NPC470149
0.8235	Intermediate Similarity	NPC475711
0.8229	Intermediate Similarity	NPC65700
0.8229	Intermediate Similarity	NPC475653
0.8222	Intermediate Similarity	NPC186332
0.8222	Intermediate Similarity	NPC47220
0.8211	Intermediate Similarity	NPC255410
0.8211	Intermediate Similarity	NPC173329
0.8211	Intermediate Similarity	NPC472995
0.8211	Intermediate Similarity	NPC288350
0.8191	Intermediate Similarity	NPC159698
0.8172	Intermediate Similarity	NPC476084
0.8172	Intermediate Similarity	NPC476075
0.8172	Intermediate Similarity	NPC184463
0.8172	Intermediate Similarity	NPC30515
0.8132	Intermediate Similarity	NPC199382
0.8125	Intermediate Similarity	NPC472998
0.8118	Intermediate Similarity	NPC469880
0.8105	Intermediate Similarity	NPC300710
0.8085	Intermediate Similarity	NPC475912
0.8068	Intermediate Similarity	NPC315731
0.8065	Intermediate Similarity	NPC473448
0.8065	Intermediate Similarity	NPC476004
0.8065	Intermediate Similarity	NPC474761
0.8065	Intermediate Similarity	NPC51004
0.8041	Intermediate Similarity	NPC203627
0.8021	Intermediate Similarity	NPC279621
0.8021	Intermediate Similarity	NPC476315
0.8	Intermediate Similarity	NPC469491
0.8	Intermediate Similarity	NPC160517
0.8	Intermediate Similarity	NPC78673
0.8	Intermediate Similarity	NPC186155
0.8	Intermediate Similarity	NPC327041
0.8	Intermediate Similarity	NPC285840
0.8	Intermediate Similarity	NPC266718
0.798	Intermediate Similarity	NPC473596
0.798	Intermediate Similarity	NPC201191
0.7979	Intermediate Similarity	NPC158061
0.7976	Intermediate Similarity	NPC327383
0.7976	Intermediate Similarity	NPC185186
0.7957	Intermediate Similarity	NPC307411
0.7938	Intermediate Similarity	NPC40812
0.7935	Intermediate Similarity	NPC316138
0.7935	Intermediate Similarity	NPC313658
0.7921	Intermediate Similarity	NPC469960
0.7921	Intermediate Similarity	NPC265502
0.7921	Intermediate Similarity	NPC239961
0.7921	Intermediate Similarity	NPC93026
0.7921	Intermediate Similarity	NPC29389
0.7917	Intermediate Similarity	NPC471141
0.7917	Intermediate Similarity	NPC14961
0.7917	Intermediate Similarity	NPC270013
0.7917	Intermediate Similarity	NPC469583
0.7912	Intermediate Similarity	NPC242233
0.79	Intermediate Similarity	NPC197736
0.7895	Intermediate Similarity	NPC81419
0.7895	Intermediate Similarity	NPC212486
0.7895	Intermediate Similarity	NPC179746
0.7889	Intermediate Similarity	NPC231601
0.7879	Intermediate Similarity	NPC57586
0.7879	Intermediate Similarity	NPC475157
0.7879	Intermediate Similarity	NPC471637
0.7879	Intermediate Similarity	NPC198992
0.7879	Intermediate Similarity	NPC2313
0.7879	Intermediate Similarity	NPC154132
0.7879	Intermediate Similarity	NPC475655
0.7879	Intermediate Similarity	NPC472554
0.7872	Intermediate Similarity	NPC475855
0.7872	Intermediate Similarity	NPC202886
0.7872	Intermediate Similarity	NPC473619
0.7872	Intermediate Similarity	NPC471569
0.7865	Intermediate Similarity	NPC474894
0.7857	Intermediate Similarity	NPC187761
0.7857	Intermediate Similarity	NPC83895
0.7857	Intermediate Similarity	NPC308567
0.7857	Intermediate Similarity	NPC187268
0.7857	Intermediate Similarity	NPC475762
0.7857	Intermediate Similarity	NPC261377
0.7857	Intermediate Similarity	NPC255592
0.7849	Intermediate Similarity	NPC280621
0.7849	Intermediate Similarity	NPC233551
0.7849	Intermediate Similarity	NPC20339
0.7849	Intermediate Similarity	NPC40376
0.7849	Intermediate Similarity	NPC48338
0.7849	Intermediate Similarity	NPC21208
0.7849	Intermediate Similarity	NPC202672
0.7843	Intermediate Similarity	NPC108682
0.7843	Intermediate Similarity	NPC472263
0.7843	Intermediate Similarity	NPC469957
0.7843	Intermediate Similarity	NPC469959
0.7841	Intermediate Similarity	NPC476701
0.7841	Intermediate Similarity	NPC86971
0.7835	Intermediate Similarity	NPC472996
0.7835	Intermediate Similarity	NPC472997
0.7826	Intermediate Similarity	NPC61527
0.7822	Intermediate Similarity	NPC472748
0.7816	Intermediate Similarity	NPC477203
0.7812	Intermediate Similarity	NPC474247
0.7812	Intermediate Similarity	NPC474035
0.7812	Intermediate Similarity	NPC81386
0.781	Intermediate Similarity	NPC328074
0.781	Intermediate Similarity	NPC317460
0.781	Intermediate Similarity	NPC321272
0.781	Intermediate Similarity	NPC470025
0.78	Intermediate Similarity	NPC472754
0.78	Intermediate Similarity	NPC470972
0.78	Intermediate Similarity	NPC149371
0.78	Intermediate Similarity	NPC472552
0.7789	Intermediate Similarity	NPC12172
0.7789	Intermediate Similarity	NPC208886
0.7789	Intermediate Similarity	NPC473321
0.7789	Intermediate Similarity	NPC477749
0.7788	Intermediate Similarity	NPC316708
0.7778	Intermediate Similarity	NPC123908
0.7778	Intermediate Similarity	NPC79631
0.7778	Intermediate Similarity	NPC38855
0.7778	Intermediate Similarity	NPC10080
0.7766	Intermediate Similarity	NPC477748
0.7765	Intermediate Similarity	NPC477085
0.7755	Intermediate Similarity	NPC205143
0.7755	Intermediate Similarity	NPC471490
0.7745	Intermediate Similarity	NPC315070
0.7745	Intermediate Similarity	NPC472751
0.7745	Intermediate Similarity	NPC472749
0.7742	Intermediate Similarity	NPC178215
0.7736	Intermediate Similarity	NPC470027
0.7732	Intermediate Similarity	NPC471142
0.7732	Intermediate Similarity	NPC304886
0.7727	Intermediate Similarity	NPC3852
0.7723	Intermediate Similarity	NPC472750
0.7723	Intermediate Similarity	NPC4620
0.7723	Intermediate Similarity	NPC472755
0.7723	Intermediate Similarity	NPC475945
0.7723	Intermediate Similarity	NPC475871
0.7723	Intermediate Similarity	NPC472747
0.7717	Intermediate Similarity	NPC322529
0.7717	Intermediate Similarity	NPC329838
0.7717	Intermediate Similarity	NPC120398
0.7717	Intermediate Similarity	NPC329615
0.7717	Intermediate Similarity	NPC477014
0.7717	Intermediate Similarity	NPC11804
0.7717	Intermediate Similarity	NPC477013
0.7717	Intermediate Similarity	NPC471567
0.7714	Intermediate Similarity	NPC470076
0.7714	Intermediate Similarity	NPC71680
0.7714	Intermediate Similarity	NPC17791
0.7714	Intermediate Similarity	NPC470026
0.7708	Intermediate Similarity	NPC295204
0.7708	Intermediate Similarity	NPC288240
0.7708	Intermediate Similarity	NPC189651
0.7708	Intermediate Similarity	NPC53555
0.7708	Intermediate Similarity	NPC162205
0.7708	Intermediate Similarity	NPC475838
0.7708	Intermediate Similarity	NPC475098
0.7708	Intermediate Similarity	NPC273579
0.7708	Intermediate Similarity	NPC228451
0.7708	Intermediate Similarity	NPC471483
0.7708	Intermediate Similarity	NPC125674
0.7701	Intermediate Similarity	NPC477202
0.77	Intermediate Similarity	NPC197447
0.77	Intermediate Similarity	NPC11974
0.77	Intermediate Similarity	NPC169365
0.77	Intermediate Similarity	NPC472753
0.77	Intermediate Similarity	NPC47880
0.7692	Intermediate Similarity	NPC27314
0.7692	Intermediate Similarity	NPC474809
0.7692	Intermediate Similarity	NPC133625
0.7692	Intermediate Similarity	NPC106912
0.7692	Intermediate Similarity	NPC2379
0.7692	Intermediate Similarity	NPC170286
0.7692	Intermediate Similarity	NPC31019
0.7692	Intermediate Similarity	NPC116543
0.7692	Intermediate Similarity	NPC263087

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 NPC177668 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	153
0.1-0.2	1423
0.2-0.3	3776
0.3-0.4	2590
0.4-0.5	820
0.5-0.6	300
0.6-0.7	78
0.7-0.8	9
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8667	High Similarity	NPD7838	Discovery
0.8261	Intermediate Similarity	NPD6698	Approved
0.8261	Intermediate Similarity	NPD46	Approved
0.7879	Intermediate Similarity	NPD5344	Discontinued
0.7857	Intermediate Similarity	NPD8029	Clinical (unspecified phase)
0.7596	Intermediate Similarity	NPD6686	Approved
0.7547	Intermediate Similarity	NPD8413	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD4225	Approved
0.75	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7426	Intermediate Similarity	NPD6648	Approved
0.7423	Intermediate Similarity	NPD7983	Approved
0.7234	Intermediate Similarity	NPD6400	Clinical (unspecified phase)
0.713	Intermediate Similarity	NPD6371	Approved
0.7105	Intermediate Similarity	NPD7503	Approved
0.701	Intermediate Similarity	NPD4250	Approved
0.701	Intermediate Similarity	NPD4251	Approved
0.7	Intermediate Similarity	NPD6053	Discontinued
0.699	Remote Similarity	NPD7638	Approved
0.6923	Remote Similarity	NPD7640	Approved
0.6923	Remote Similarity	NPD7639	Approved
0.6907	Remote Similarity	NPD4249	Approved
0.6863	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD7328	Approved
0.6842	Remote Similarity	NPD7327	Approved
0.6832	Remote Similarity	NPD5779	Approved
0.6832	Remote Similarity	NPD5778	Approved
0.681	Remote Similarity	NPD8513	Phase 3
0.681	Remote Similarity	NPD8033	Approved
0.6809	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6804	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6783	Remote Similarity	NPD7516	Approved
0.6771	Remote Similarity	NPD7154	Phase 3
0.6754	Remote Similarity	NPD7115	Discovery
0.6733	Remote Similarity	NPD7637	Suspended
0.6724	Remote Similarity	NPD8377	Approved
0.6724	Remote Similarity	NPD8294	Approved
0.6667	Remote Similarity	NPD8296	Approved
0.6667	Remote Similarity	NPD8335	Approved
0.6667	Remote Similarity	NPD8380	Approved
0.6667	Remote Similarity	NPD8517	Approved
0.6667	Remote Similarity	NPD8379	Approved
0.6667	Remote Similarity	NPD8516	Approved
0.6667	Remote Similarity	NPD8515	Approved
0.6667	Remote Similarity	NPD7524	Approved
0.6667	Remote Similarity	NPD8378	Approved
0.6634	Remote Similarity	NPD5785	Approved
0.6633	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6632	Remote Similarity	NPD4822	Approved
0.6632	Remote Similarity	NPD4819	Approved
0.6632	Remote Similarity	NPD4821	Approved
0.6632	Remote Similarity	NPD4820	Approved
0.6609	Remote Similarity	NPD7505	Discontinued
0.6596	Remote Similarity	NPD4268	Approved
0.6596	Remote Similarity	NPD4271	Approved
0.6577	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6555	Remote Similarity	NPD7829	Approved
0.6555	Remote Similarity	NPD7830	Approved
0.6552	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6535	Remote Similarity	NPD1695	Approved
0.6531	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6495	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6476	Remote Similarity	NPD7839	Suspended
0.6476	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.6465	Remote Similarity	NPD5363	Approved
0.6465	Remote Similarity	NPD1694	Approved
0.6446	Remote Similarity	NPD7507	Approved
0.6442	Remote Similarity	NPD5282	Discontinued
0.6429	Remote Similarity	NPD5362	Discontinued
0.6429	Remote Similarity	NPD6695	Phase 3
0.6396	Remote Similarity	NPD6412	Phase 2
0.6393	Remote Similarity	NPD8074	Phase 3
0.6373	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6373	Remote Similarity	NPD6101	Approved
0.6372	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.633	Remote Similarity	NPD7632	Discontinued
0.6328	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6327	Remote Similarity	NPD6435	Approved
0.6303	Remote Similarity	NPD6319	Approved
0.629	Remote Similarity	NPD7319	Approved
0.6281	Remote Similarity	NPD7642	Approved
0.6271	Remote Similarity	NPD7641	Discontinued
0.6263	Remote Similarity	NPD6110	Phase 1
0.6263	Remote Similarity	NPD5332	Approved
0.6263	Remote Similarity	NPD5331	Approved
0.6261	Remote Similarity	NPD8297	Approved
0.625	Remote Similarity	NPD6411	Approved
0.6224	Remote Similarity	NPD4790	Discontinued
0.6207	Remote Similarity	NPD4632	Approved
0.619	Remote Similarity	NPD7260	Phase 2
0.6186	Remote Similarity	NPD6929	Approved
0.6179	Remote Similarity	NPD8273	Phase 1
0.6179	Remote Similarity	NPD8451	Approved
0.6176	Remote Similarity	NPD7750	Discontinued
0.6162	Remote Similarity	NPD4270	Approved
0.6162	Remote Similarity	NPD4269	Approved
0.6162	Remote Similarity	NPD5209	Approved
0.6129	Remote Similarity	NPD8448	Approved
0.6122	Remote Similarity	NPD7514	Phase 3
0.6122	Remote Similarity	NPD6930	Phase 2
0.6122	Remote Similarity	NPD6931	Approved
0.6122	Remote Similarity	NPD7332	Phase 2
0.6122	Remote Similarity	NPD5368	Approved
0.6116	Remote Similarity	NPD8444	Approved
0.6106	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6098	Remote Similarity	NPD7492	Approved
0.6087	Remote Similarity	NPD6421	Discontinued
0.6082	Remote Similarity	NPD7145	Approved
0.6082	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6078	Remote Similarity	NPD5786	Approved
0.6068	Remote Similarity	NPD8133	Approved
0.6061	Remote Similarity	NPD6902	Approved
0.6061	Remote Similarity	NPD5369	Approved
0.6058	Remote Similarity	NPD6051	Approved
0.6053	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6053	Remote Similarity	NPD6899	Approved
0.6053	Remote Similarity	NPD6881	Approved
0.605	Remote Similarity	NPD7500	Approved
0.6048	Remote Similarity	NPD6616	Approved
0.6042	Remote Similarity	NPD6933	Approved
0.6038	Remote Similarity	NPD6399	Phase 3
0.6034	Remote Similarity	NPD7116	Clinical (unspecified phase)
0.6034	Remote Similarity	NPD6650	Approved
0.6034	Remote Similarity	NPD6649	Approved
0.6033	Remote Similarity	NPD6054	Approved
0.6018	Remote Similarity	NPD4211	Phase 1
0.6018	Remote Similarity	NPD6640	Phase 3
0.6	Remote Similarity	NPD7078	Approved
0.5984	Remote Similarity	NPD8390	Approved
0.5984	Remote Similarity	NPD8392	Approved
0.5984	Remote Similarity	NPD8391	Approved
0.5983	Remote Similarity	NPD6882	Approved
0.5979	Remote Similarity	NPD5776	Phase 2
0.5979	Remote Similarity	NPD6925	Approved
0.5979	Remote Similarity	NPD6932	Approved
0.5968	Remote Similarity	NPD8340	Approved
0.5968	Remote Similarity	NPD8342	Approved
0.5968	Remote Similarity	NPD8341	Approved
0.5968	Remote Similarity	NPD8299	Approved
0.5965	Remote Similarity	NPD5697	Approved
0.5963	Remote Similarity	NPD6083	Phase 2
0.5963	Remote Similarity	NPD6084	Phase 2
0.596	Remote Similarity	NPD4252	Approved
0.5952	Remote Similarity	NPD7736	Approved
0.5948	Remote Similarity	NPD7102	Approved
0.5948	Remote Similarity	NPD7290	Approved
0.5948	Remote Similarity	NPD6883	Approved
0.5943	Remote Similarity	NPD7087	Discontinued
0.5938	Remote Similarity	NPD8039	Approved
0.5935	Remote Similarity	NPD6370	Approved
0.5917	Remote Similarity	NPD6009	Approved
0.5897	Remote Similarity	NPD6847	Approved
0.5897	Remote Similarity	NPD6869	Approved
0.5897	Remote Similarity	NPD6617	Approved
0.5897	Remote Similarity	NPD8130	Phase 1
0.5891	Remote Similarity	NPD6845	Suspended
0.5889	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.5887	Remote Similarity	NPD8328	Phase 3
0.5887	Remote Similarity	NPD7604	Phase 2
0.5877	Remote Similarity	NPD7128	Approved
0.5877	Remote Similarity	NPD6402	Approved
0.5877	Remote Similarity	NPD6675	Approved
0.5877	Remote Similarity	NPD5739	Approved
0.5862	Remote Similarity	NPD6012	Approved
0.5862	Remote Similarity	NPD6373	Approved
0.5862	Remote Similarity	NPD6014	Approved
0.5862	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.5862	Remote Similarity	NPD6372	Approved
0.5862	Remote Similarity	NPD6013	Approved
0.5854	Remote Similarity	NPD6015	Approved
0.5854	Remote Similarity	NPD5983	Phase 2
0.5854	Remote Similarity	NPD6016	Approved
0.5851	Remote Similarity	NPD7532	Clinical (unspecified phase)
0.5849	Remote Similarity	NPD3168	Discontinued
0.5841	Remote Similarity	NPD6647	Phase 2
0.5833	Remote Similarity	NPD6924	Approved
0.5833	Remote Similarity	NPD6926	Approved
0.5833	Remote Similarity	NPD7748	Approved
0.5826	Remote Similarity	NPD6685	Approved
0.5825	Remote Similarity	NPD6893	Approved
0.5818	Remote Similarity	NPD7902	Approved
0.5806	Remote Similarity	NPD5126	Approved
0.5806	Remote Similarity	NPD5988	Approved
0.5806	Remote Similarity	NPD5125	Phase 3
0.5806	Remote Similarity	NPD8080	Discontinued
0.5794	Remote Similarity	NPD6336	Discontinued
0.5794	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.5794	Remote Similarity	NPD7515	Phase 2
0.5785	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.578	Remote Similarity	NPD5695	Phase 3
0.5776	Remote Similarity	NPD6011	Approved
0.5776	Remote Similarity	NPD7320	Approved
0.5773	Remote Similarity	NPD8264	Approved
0.5772	Remote Similarity	NPD6059	Approved
0.5769	Remote Similarity	NPD5330	Approved
0.5769	Remote Similarity	NPD7521	Approved
0.5769	Remote Similarity	NPD7334	Approved
0.5769	Remote Similarity	NPD6684	Approved
0.5769	Remote Similarity	NPD6409	Approved
0.5769	Remote Similarity	NPD7146	Approved
0.5758	Remote Similarity	NPD7322	Clinical (unspecified phase)

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