NPASS Compound

Structure

NPC471856 OpenBabel07101719132D 47 55 0 0 1 0 0 0 0 0999 V2000 -0.1229 3.1254 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5945 -0.5303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1926 -2.0303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5945 -3.5303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.5227 1.4697 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.5227 0.4697 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.6567 1.9697 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.6567 -0.0303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.7907 1.4697 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3266 0.4697 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0649 -1.4476 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7285 -1.0303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4606 -0.0303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8625 -1.5303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4716 -2.3612 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0586 0.4697 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3266 -2.5303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6092 0.1691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1229 1.1691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8625 -3.5303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0796 2.2518 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0586 -1.5303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.7907 0.4697 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1926 -0.0303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4013 -0.8090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.0704 -1.5522 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 7.9247 -0.0303 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.5945 -1.5303 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.3266 -1.5303 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.4606 -3.0303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4067 -0.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0739 3.4344 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0850 2.1473 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.4606 -1.0303 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 6.1926 -1.0303 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.5945 -2.5303 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.8625 -2.5303 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.7285 -3.0303 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.7431 0.6691 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.4606 -4.0303 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0933 -1.7796 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3308 4.1036 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.0250 3.7435 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.9247 -1.0303 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4863 1.3383 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 -0.8660 2.4563 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4 36 1 0 0 0 0 5 6 2 0 0 0 0 5 7 1 0 0 0 0 6 8 1 0 0 0 0 7 9 2 0 0 0 0 8 23 2 0 0 0 0 9 23 1 0 0 0 0 10 13 1 0 0 0 0 10 24 2 0 0 0 0 11 15 1 0 0 0 0 11 26 1 0 0 0 0 12 14 2 0 0 0 0 12 28 1 0 0 0 0 13 34 1 0 0 0 0 14 37 1 0 0 0 0 16 24 1 0 0 0 0 16 27 1 0 0 0 0 17 29 1 0 0 0 0 17 30 1 0 0 0 0 19 33 1 0 0 0 0 19 39 1 0 0 0 0 20 37 1 0 0 0 0 20 38 1 0 0 0 0 21 33 1 0 0 0 0 21 45 1 0 0 0 0 22 35 1 0 0 0 0 22 44 1 0 0 0 0 24 35 1 0 0 0 0 25 18 1 1 0 0 0 25 26 1 0 0 0 0 25 31 1 0 0 0 0 26 37 1 6 0 0 0 27 23 1 1 0 0 0 27 44 1 0 0 0 0 28 34 1 6 0 0 0 28 36 1 0 0 0 0 29 34 1 6 0 0 0 29 35 1 0 0 0 0 30 36 1 0 0 0 0 30 40 2 0 0 0 0 31 41 2 0 0 0 0 31 46 1 0 0 0 0 32 42 2 0 0 0 0 32 43 1 0 0 0 0 32 47 1 0 0 0 0 33 1 1 6 0 0 0 33 47 1 0 0 0 0 34 2 1 6 0 0 0 35 3 1 1 0 0 0 36 38 1 1 0 0 0 37 38 1 1 0 0 0 38 15 1 6 0 0 0 39 18 1 1 0 0 0 39 45 1 0 0 0 0 39 46 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	642.32
Volume:	655.322
LogP:	4.532
LogD:	2.441
LogS:	-5.06
# Rotatable Bonds:	4
TPSA:	108.36
# H-Bond Aceptor:	8
# H-Bond Donor:	1
# Rings:	9
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.273
Synthetic Accessibility Score:	6.457
Fsp3:	0.667
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:	-5.481
MDCK Permeability:	1.6438647435279563e-05
Pgp-inhibitor:	0.778
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.002
20% Bioavailability (F20%):	0.715
30% Bioavailability (F30%):	0.279

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.992
Plasma Protein Binding (PPB):	79.2003402709961%
Volume Distribution (VD):	0.355
Pgp-substrate:	11.879565238952637%

ADMET: Metabolism

CYP1A2-inhibitor:	0.003
CYP1A2-substrate:	0.784
CYP2C19-inhibitor:	0.074
CYP2C19-substrate:	0.836
CYP2C9-inhibitor:	0.233
CYP2C9-substrate:	0.053
CYP2D6-inhibitor:	0.009
CYP2D6-substrate:	0.08
CYP3A4-inhibitor:	0.749
CYP3A4-substrate:	0.628

ADMET: Excretion

Clearance (CL):	10.046
Half-life (T1/2):	0.452

ADMET: Toxicity

hERG Blockers:	0.207
Human Hepatotoxicity (H-HT):	0.475
Drug-inuced Liver Injury (DILI):	0.575
AMES Toxicity:	0.114
Rat Oral Acute Toxicity:	0.943
Maximum Recommended Daily Dose:	0.963
Skin Sensitization:	0.158
Carcinogencity:	0.252
Eye Corrosion:	0.003
Eye Irritation:	0.008
Respiratory Toxicity:	0.944

Download Data

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

Natural Product: NPC471856

Natural Product ID:	NPC471856
*Common Name:**	FGPLCBKMJPRSOY-DBKNPJPYSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	FGPLCBKMJPRSOY-DBKNPJPYSA-N
Standard InCHI:	InChI=1S/C39H46O8/c1-33(47-32(42)43)19-39(45-21-33)18-25(31(41)46-39)26-11-15-38-20-37(26,38)14-12-28-34(2)13-10-24-16-27(23-8-6-5-7-9-23)44-22-35(24,3)29(34)17-30(40)36(28,38)4/h5-10,12,14,25-29H,11,13,15-22H2,1-4H3,(H,42,43)/t25-,26-,27-,28+,29+,33+,34+,35-,36-,37+,38+,39+/m0/s1
SMILES:	CC12CC=C3CC(OCC3(C1CC(=O)C4(C2C=CC56C4(C5)CCC6C7CC8(CC(CO8)(C)OC(=O)O)OC7=O)C)C)C9=CC=CC=C9
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3261934
PubChem CID:	90676169
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO9878	Dichapetalum gelonioides	Species	Dichapetalaceae	Eukaryota	stem bark	Philippines	n.a.	PMID[16562829]
NPO9878	Dichapetalum gelonioides	Species	Dichapetalaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24597894]
NPO9878	Dichapetalum gelonioides	Species	Dichapetalaceae	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
EC50	1
Others	4

Activity Type	# Activity
Organism	4
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2779	Organism	Spodoptera exigua	Spodoptera exigua	EC50	=	11.7	microg/cm2	PMID[564497]
NPT1272	Organism	Panagrellus redivivus	Panagrellus redivivus	mortality	=	7.0	%	PMID[564497]
NPT562	Organism	Colletotrichum gloeosporioides	Colletotrichum gloeosporioides	IZ	=	10.1	mm	PMID[564497]
NPT610	Others	Molecular identity unknown		IZ	=	13.8	mm	PMID[564497]
NPT5164	Organism	Fusarium oxysporum f. sp. niveum	Fusarium oxysporum f. sp. niveum	IZ	=	11.5	mm	PMID[564497]

☑ 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 NPC471856 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	329
0.1-0.2	1198
0.2-0.3	2496
0.3-0.4	5563
0.4-0.5	12783
0.5-0.6	16869
0.6-0.7	2979
0.7-0.8	464
0.8-0.85	7
0.85-0.9	7
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.963	High Similarity	NPC471862
0.875	High Similarity	NPC471858
0.8699	High Similarity	NPC475417
0.8699	High Similarity	NPC475561
0.8693	High Similarity	NPC471850
0.8516	High Similarity	NPC471861
0.8471	Intermediate Similarity	NPC471860
0.8471	Intermediate Similarity	NPC471859
0.8451	Intermediate Similarity	NPC243893
0.8333	Intermediate Similarity	NPC79921
0.8322	Intermediate Similarity	NPC262324
0.8158	Intermediate Similarity	NPC472657
0.8158	Intermediate Similarity	NPC472658
0.8056	Intermediate Similarity	NPC471864
0.7975	Intermediate Similarity	NPC478073
0.7973	Intermediate Similarity	NPC472235
0.7973	Intermediate Similarity	NPC472236
0.7972	Intermediate Similarity	NPC471880
0.7935	Intermediate Similarity	NPC154675
0.7902	Intermediate Similarity	NPC470278
0.7879	Intermediate Similarity	NPC475244
0.7875	Intermediate Similarity	NPC477491
0.7871	Intermediate Similarity	NPC469456
0.7862	Intermediate Similarity	NPC203486
0.7838	Intermediate Similarity	NPC475400
0.7834	Intermediate Similarity	NPC476784
0.7818	Intermediate Similarity	NPC473467
0.7818	Intermediate Similarity	NPC475197
0.78	Intermediate Similarity	NPC131966
0.78	Intermediate Similarity	NPC191387
0.7792	Intermediate Similarity	NPC253591
0.7764	Intermediate Similarity	NPC325732
0.7764	Intermediate Similarity	NPC324769
0.7742	Intermediate Similarity	NPC472548
0.774	Intermediate Similarity	NPC329913
0.7733	Intermediate Similarity	NPC475135
0.773	Intermediate Similarity	NPC477488
0.7724	Intermediate Similarity	NPC475493
0.7724	Intermediate Similarity	NPC469499
0.7722	Intermediate Similarity	NPC49297
0.7718	Intermediate Similarity	NPC183270
0.7718	Intermediate Similarity	NPC477904
0.7707	Intermediate Similarity	NPC475638
0.7707	Intermediate Similarity	NPC326235
0.7707	Intermediate Similarity	NPC290683
0.7707	Intermediate Similarity	NPC323001
0.7707	Intermediate Similarity	NPC471863
0.7707	Intermediate Similarity	NPC475548
0.7703	Intermediate Similarity	NPC205305
0.7703	Intermediate Similarity	NPC327511
0.7692	Intermediate Similarity	NPC471135
0.7692	Intermediate Similarity	NPC261659
0.7688	Intermediate Similarity	NPC275477
0.7687	Intermediate Similarity	NPC473216
0.7687	Intermediate Similarity	NPC473399
0.7676	Intermediate Similarity	NPC9180
0.7676	Intermediate Similarity	NPC100402
0.7673	Intermediate Similarity	NPC309991
0.7673	Intermediate Similarity	NPC326328
0.7673	Intermediate Similarity	NPC323356
0.7673	Intermediate Similarity	NPC471138
0.7673	Intermediate Similarity	NPC477623
0.7671	Intermediate Similarity	NPC159811
0.7669	Intermediate Similarity	NPC469420
0.7669	Intermediate Similarity	NPC40138
0.7667	Intermediate Similarity	NPC325078
0.7667	Intermediate Similarity	NPC187566
0.7662	Intermediate Similarity	NPC472938
0.7662	Intermediate Similarity	NPC472937
0.7662	Intermediate Similarity	NPC472936
0.7658	Intermediate Similarity	NPC469417
0.7658	Intermediate Similarity	NPC318447
0.7658	Intermediate Similarity	NPC181924
0.7658	Intermediate Similarity	NPC322048
0.7651	Intermediate Similarity	NPC53361
0.7651	Intermediate Similarity	NPC121268
0.7647	Intermediate Similarity	NPC170668
0.7643	Intermediate Similarity	NPC471176
0.7643	Intermediate Similarity	NPC34066
0.7643	Intermediate Similarity	NPC472549
0.7643	Intermediate Similarity	NPC469422
0.764	Intermediate Similarity	NPC322420
0.7628	Intermediate Similarity	NPC477905
0.7628	Intermediate Similarity	NPC472939
0.7619	Intermediate Similarity	NPC471911
0.7619	Intermediate Similarity	NPC4242
0.7619	Intermediate Similarity	NPC134937
0.7619	Intermediate Similarity	NPC324898
0.7619	Intermediate Similarity	NPC298547
0.7619	Intermediate Similarity	NPC126516
0.7616	Intermediate Similarity	NPC63737
0.7613	Intermediate Similarity	NPC476173
0.7613	Intermediate Similarity	NPC125033
0.7613	Intermediate Similarity	NPC469448
0.7603	Intermediate Similarity	NPC472394
0.76	Intermediate Similarity	NPC473440
0.759	Intermediate Similarity	NPC469421
0.7586	Intermediate Similarity	NPC475508
0.7584	Intermediate Similarity	NPC475373
0.7578	Intermediate Similarity	NPC43304
0.7578	Intermediate Similarity	NPC477190
0.7578	Intermediate Similarity	NPC475536
0.7578	Intermediate Similarity	NPC477188
0.7578	Intermediate Similarity	NPC478124
0.7578	Intermediate Similarity	NPC165234
0.7568	Intermediate Similarity	NPC149401
0.7568	Intermediate Similarity	NPC200154
0.7568	Intermediate Similarity	NPC279637
0.7566	Intermediate Similarity	NPC153214
0.7564	Intermediate Similarity	NPC478123
0.7564	Intermediate Similarity	NPC62792
0.7564	Intermediate Similarity	NPC469415
0.7561	Intermediate Similarity	NPC102465
0.7552	Intermediate Similarity	NPC470816
0.7552	Intermediate Similarity	NPC470818
0.7551	Intermediate Similarity	NPC472656
0.755	Intermediate Similarity	NPC242355
0.755	Intermediate Similarity	NPC16912
0.7546	Intermediate Similarity	NPC61891
0.7546	Intermediate Similarity	NPC473557
0.7546	Intermediate Similarity	NPC473468
0.7546	Intermediate Similarity	NPC475567
0.7536	Intermediate Similarity	NPC45794
0.7535	Intermediate Similarity	NPC138798
0.7535	Intermediate Similarity	NPC469742
0.7534	Intermediate Similarity	NPC472418
0.7533	Intermediate Similarity	NPC472395
0.7533	Intermediate Similarity	NPC276652
0.7533	Intermediate Similarity	NPC472371
0.7532	Intermediate Similarity	NPC469398
0.7532	Intermediate Similarity	NPC474935
0.7532	Intermediate Similarity	NPC473602
0.7531	Intermediate Similarity	NPC475464
0.7531	Intermediate Similarity	NPC295408
0.7531	Intermediate Similarity	NPC329960
0.7531	Intermediate Similarity	NPC473641
0.7531	Intermediate Similarity	NPC473797
0.7531	Intermediate Similarity	NPC66193
0.7531	Intermediate Similarity	NPC475437
0.7531	Intermediate Similarity	NPC475300
0.7531	Intermediate Similarity	NPC150893
0.7531	Intermediate Similarity	NPC475505
0.7517	Intermediate Similarity	NPC477358
0.7517	Intermediate Similarity	NPC225103
0.7516	Intermediate Similarity	NPC138641
0.7516	Intermediate Similarity	NPC471139
0.7516	Intermediate Similarity	NPC188865
0.7516	Intermediate Similarity	NPC283875
0.7516	Intermediate Similarity	NPC95265
0.7516	Intermediate Similarity	NPC469648
0.7516	Intermediate Similarity	NPC469647
0.7516	Intermediate Similarity	NPC25768
0.7516	Intermediate Similarity	NPC11685
0.7516	Intermediate Similarity	NPC472569
0.7516	Intermediate Similarity	NPC70716
0.7516	Intermediate Similarity	NPC125106
0.7516	Intermediate Similarity	NPC95810
0.7516	Intermediate Similarity	NPC476974
0.7516	Intermediate Similarity	NPC57628
0.7516	Intermediate Similarity	NPC472573
0.7516	Intermediate Similarity	NPC163719
0.7516	Intermediate Similarity	NPC22571
0.7516	Intermediate Similarity	NPC472570
0.75	Intermediate Similarity	NPC195972
0.75	Intermediate Similarity	NPC477359
0.75	Intermediate Similarity	NPC477368
0.75	Intermediate Similarity	NPC319404
0.75	Intermediate Similarity	NPC475175
0.75	Intermediate Similarity	NPC475531
0.75	Intermediate Similarity	NPC303429
0.75	Intermediate Similarity	NPC469399
0.75	Intermediate Similarity	NPC140021
0.75	Intermediate Similarity	NPC222102
0.75	Intermediate Similarity	NPC153617
0.75	Intermediate Similarity	NPC51292
0.75	Intermediate Similarity	NPC475198
0.7485	Intermediate Similarity	NPC471134
0.7484	Intermediate Similarity	NPC281717
0.7484	Intermediate Similarity	NPC70344
0.7483	Intermediate Similarity	NPC48017
0.7483	Intermediate Similarity	NPC473112
0.7483	Intermediate Similarity	NPC147880
0.7483	Intermediate Similarity	NPC473613
0.7483	Intermediate Similarity	NPC473109
0.7483	Intermediate Similarity	NPC4341
0.7483	Intermediate Similarity	NPC473060
0.7483	Intermediate Similarity	NPC200592
0.7483	Intermediate Similarity	NPC90614
0.7483	Intermediate Similarity	NPC472547
0.7483	Intermediate Similarity	NPC43241
0.7483	Intermediate Similarity	NPC211137
0.7483	Intermediate Similarity	NPC209851
0.7483	Intermediate Similarity	NPC475660
0.7483	Intermediate Similarity	NPC184747
0.7483	Intermediate Similarity	NPC171207
0.7483	Intermediate Similarity	NPC475651
0.7483	Intermediate Similarity	NPC233860
0.7483	Intermediate Similarity	NPC251294
0.7483	Intermediate Similarity	NPC473758
0.7483	Intermediate Similarity	NPC476094

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 NPC471856 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	265
0.1-0.2	761
0.2-0.3	1589
0.3-0.4	3237
0.4-0.5	2288
0.5-0.6	901
0.6-0.7	103
0.7-0.8	6
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
0.7582	Intermediate Similarity	NPD7236	Approved
0.7576	Intermediate Similarity	NPD7799	Discontinued
0.7466	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7452	Intermediate Similarity	NPD7239	Suspended
0.7324	Intermediate Similarity	NPD7457	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD7966	Clinical (unspecified phase)
0.7174	Intermediate Similarity	NPD7094	Approved
0.7174	Intermediate Similarity	NPD6858	Approved
0.7143	Intermediate Similarity	NPD7028	Phase 2
0.7133	Intermediate Similarity	NPD5125	Phase 3
0.7133	Intermediate Similarity	NPD5126	Approved
0.7113	Intermediate Similarity	NPD7741	Discontinued
0.703	Intermediate Similarity	NPD7058	Phase 2
0.703	Intermediate Similarity	NPD7057	Phase 3
0.7021	Intermediate Similarity	NPD4198	Discontinued
0.7014	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.7013	Intermediate Similarity	NPD7305	Phase 1
0.695	Remote Similarity	NPD2629	Approved
0.6948	Remote Similarity	NPD7097	Phase 1
0.6932	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6908	Remote Similarity	NPD6663	Approved
0.6908	Remote Similarity	NPD7961	Discontinued
0.6899	Remote Similarity	NPD8166	Discontinued
0.6875	Remote Similarity	NPD8407	Phase 2
0.686	Remote Similarity	NPD7228	Approved
0.6832	Remote Similarity	NPD8389	Clinical (unspecified phase)
0.6826	Remote Similarity	NPD4965	Approved
0.6826	Remote Similarity	NPD4966	Approved
0.6826	Remote Similarity	NPD4967	Phase 2
0.6821	Remote Similarity	NPD8470	Clinical (unspecified phase)
0.6821	Remote Similarity	NPD7055	Discontinued
0.68	Remote Similarity	NPD6085	Phase 2
0.68	Remote Similarity	NPD5740	Clinical (unspecified phase)
0.68	Remote Similarity	NPD8368	Discontinued
0.6798	Remote Similarity	NPD8424	Clinical (unspecified phase)
0.6797	Remote Similarity	NPD8032	Phase 2
0.6786	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6768	Remote Similarity	NPD7458	Discontinued
0.6765	Remote Similarity	NPD8127	Discontinued
0.6761	Remote Similarity	NPD6010	Discontinued
0.6755	Remote Similarity	NPD5736	Approved
0.6746	Remote Similarity	NPD6234	Discontinued
0.6705	Remote Similarity	NPD7240	Approved
0.6689	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7008	Discontinued
0.6647	Remote Similarity	NPD37	Approved
0.6645	Remote Similarity	NPD7084	Phase 3
0.661	Remote Similarity	NPD7685	Pre-registration
0.6607	Remote Similarity	NPD8455	Phase 2
0.6604	Remote Similarity	NPD7702	Clinical (unspecified phase)
0.6603	Remote Similarity	NPD6355	Discontinued
0.6596	Remote Similarity	NPD2067	Discontinued
0.6581	Remote Similarity	NPD7715	Approved
0.6581	Remote Similarity	NPD7714	Approved
0.657	Remote Similarity	NPD7199	Phase 2
0.6554	Remote Similarity	NPD2932	Approved
0.6544	Remote Similarity	NPD7798	Approved
0.6538	Remote Similarity	NPD8361	Approved
0.6538	Remote Similarity	NPD8435	Approved
0.6538	Remote Similarity	NPD8360	Approved
0.6525	Remote Similarity	NPD2182	Approved
0.6524	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6519	Remote Similarity	NPD8150	Discontinued
0.6519	Remote Similarity	NPD8434	Phase 2
0.6503	Remote Similarity	NPD969	Suspended
0.65	Remote Similarity	NPD6685	Approved
0.65	Remote Similarity	NPD6005	Phase 3
0.65	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.65	Remote Similarity	NPD6004	Phase 3
0.65	Remote Similarity	NPD6002	Phase 3
0.65	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6494	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6485	Remote Similarity	NPD6273	Approved
0.6483	Remote Similarity	NPD690	Clinical (unspecified phase)
0.6481	Remote Similarity	NPD4110	Phase 3
0.6481	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6453	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.6447	Remote Similarity	NPD5667	Approved
0.6444	Remote Similarity	NPD8312	Approved
0.6444	Remote Similarity	NPD8313	Approved
0.6443	Remote Similarity	NPD3019	Approved
0.6438	Remote Similarity	NPD2438	Suspended
0.6433	Remote Similarity	NPD4140	Approved
0.6425	Remote Similarity	NPD6765	Approved
0.6425	Remote Similarity	NPD6764	Approved
0.6419	Remote Similarity	NPD7009	Phase 2
0.6408	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6403	Remote Similarity	NPD5738	Clinical (unspecified phase)
0.6402	Remote Similarity	NPD8486	Clinical (unspecified phase)
0.64	Remote Similarity	NPD3026	Approved
0.64	Remote Similarity	NPD3023	Approved
0.6398	Remote Similarity	NPD5763	Approved
0.6398	Remote Similarity	NPD5762	Approved
0.6389	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.6378	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6376	Remote Similarity	NPD3025	Approved
0.6376	Remote Similarity	NPD3024	Approved
0.6376	Remote Similarity	NPD5585	Approved
0.637	Remote Similarity	NPD5951	Approved
0.637	Remote Similarity	NPD4766	Approved
0.6369	Remote Similarity	NPD6591	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD5647	Approved
0.6359	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6358	Remote Similarity	NPD6287	Discontinued
0.6358	Remote Similarity	NPD4806	Approved
0.6358	Remote Similarity	NPD4807	Approved
0.6357	Remote Similarity	NPD5909	Discontinued
0.6352	Remote Similarity	NPD6653	Approved
0.6351	Remote Similarity	NPD7610	Discontinued
0.6335	Remote Similarity	NPD7137	Phase 2
0.6333	Remote Similarity	NPD5306	Approved
0.6333	Remote Similarity	NPD7163	Clinical (unspecified phase)
0.6333	Remote Similarity	NPD5305	Approved
0.6329	Remote Similarity	NPD6311	Approved
0.6329	Remote Similarity	NPD6309	Approved
0.6329	Remote Similarity	NPD6310	Approved
0.6327	Remote Similarity	NPD3317	Approved
0.6327	Remote Similarity	NPD7115	Discovery
0.6323	Remote Similarity	NPD3662	Phase 3
0.6323	Remote Similarity	NPD3661	Approved
0.6323	Remote Similarity	NPD3664	Approved
0.6323	Remote Similarity	NPD3663	Approved
0.6302	Remote Similarity	NPD7680	Approved
0.6286	Remote Similarity	NPD5765	Approved
0.6286	Remote Similarity	NPD6647	Phase 2
0.6284	Remote Similarity	NPD6784	Approved
0.6284	Remote Similarity	NPD6785	Approved
0.628	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.628	Remote Similarity	NPD4628	Phase 3
0.6276	Remote Similarity	NPD6912	Phase 3
0.6266	Remote Similarity	NPD6233	Phase 2
0.6266	Remote Similarity	NPD7713	Phase 3
0.6265	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.625	Remote Similarity	NPD1693	Approved
0.625	Remote Similarity	NPD6353	Approved
0.625	Remote Similarity	NPD3787	Discontinued
0.625	Remote Similarity	NPD5618	Discontinued
0.6243	Remote Similarity	NPD8485	Approved
0.6242	Remote Similarity	NPD6065	Approved
0.6242	Remote Similarity	NPD7095	Approved
0.6241	Remote Similarity	NPD164	Approved
0.6235	Remote Similarity	NPD6099	Approved
0.6235	Remote Similarity	NPD6100	Approved
0.6226	Remote Similarity	NPD5120	Approved
0.6226	Remote Similarity	NPD2979	Phase 3
0.6226	Remote Similarity	NPD5121	Approved
0.6226	Remote Similarity	NPD5119	Approved
0.6221	Remote Similarity	NPD5761	Phase 2
0.6221	Remote Similarity	NPD5760	Phase 2
0.6218	Remote Similarity	NPD5204	Approved
0.6209	Remote Similarity	NPD7507	Approved
0.6207	Remote Similarity	NPD4141	Clinical (unspecified phase)
0.6204	Remote Similarity	NPD1989	Approved
0.6203	Remote Similarity	NPD3268	Approved
0.6203	Remote Similarity	NPD3764	Approved
0.6203	Remote Similarity	NPD6798	Discontinued
0.6203	Remote Similarity	NPD7985	Registered
0.62	Remote Similarity	NPD4479	Discontinued
0.6196	Remote Similarity	NPD7266	Discontinued
0.6196	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6196	Remote Similarity	NPD2346	Discontinued
0.6194	Remote Similarity	NPD6362	Approved
0.6188	Remote Similarity	NPD5735	Approved
0.6187	Remote Similarity	NPD2066	Phase 3
0.6184	Remote Similarity	NPD4135	Approved
0.6184	Remote Similarity	NPD4136	Approved
0.6184	Remote Similarity	NPD4106	Approved
0.6182	Remote Similarity	NPD7488	Clinical (unspecified phase)
0.6182	Remote Similarity	NPD7003	Approved
0.6178	Remote Similarity	NPD5201	Approved
0.6178	Remote Similarity	NPD5203	Approved
0.6178	Remote Similarity	NPD4617	Approved
0.6178	Remote Similarity	NPD4620	Approved
0.6178	Remote Similarity	NPD7237	Clinical (unspecified phase)
0.6176	Remote Similarity	NPD5122	Clinical (unspecified phase)
0.6174	Remote Similarity	NPD4230	Clinical (unspecified phase)
0.6173	Remote Similarity	NPD7033	Discontinued
0.6169	Remote Similarity	NPD5327	Phase 3
0.6169	Remote Similarity	NPD4359	Approved
0.6167	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6159	Remote Similarity	NPD8513	Phase 3
0.6159	Remote Similarity	NPD8515	Approved
0.6159	Remote Similarity	NPD8517	Approved
0.6159	Remote Similarity	NPD8516	Approved
0.6159	Remote Similarity	NPD7503	Approved
0.6158	Remote Similarity	NPD7315	Approved
0.6134	Remote Similarity	NPD7497	Discontinued
0.6131	Remote Similarity	NPD8462	Phase 1
0.6129	Remote Similarity	NPD1283	Approved
0.6127	Remote Similarity	NPD7819	Suspended
0.6111	Remote Similarity	NPD3751	Discontinued
0.6105	Remote Similarity	NPD6677	Suspended
0.6105	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6103	Remote Similarity	NPD8320	Phase 1
0.6103	Remote Similarity	NPD8319	Approved
0.6103	Remote Similarity	NPD6399	Phase 3
0.6103	Remote Similarity	NPD1088	Approved
0.609	Remote Similarity	NPD3094	Phase 2
0.609	Remote Similarity	NPD3266	Approved
0.609	Remote Similarity	NPD7319	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