NPASS Compound

Structure

NPC471563 OpenBabel07101718192D 57 61 0 0 1 0 0 0 0 0999 V2000 2.7873 3.3218 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0898 1.4152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7873 -4.3048 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5427 -1.1537 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9680 0.1707 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3362 -3.4126 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 11.1974 -0.4322 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4284 -1.5611 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7923 -0.4322 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6436 -1.9067 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7499 -1.3908 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5626 -2.1407 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6436 0.0593 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.4949 -1.4152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4903 -0.7242 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1510 -1.6108 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0898 -2.3981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0220 -2.3026 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0220 1.3196 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5626 1.1577 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9946 0.1740 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7873 2.3389 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.2385 0.9237 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.7873 -3.3218 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 7.7923 -1.4152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8095 -2.3853 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8095 1.4024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.4949 -0.4322 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4731 -0.8874 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2385 -1.9067 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.3362 0.9237 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.3362 -1.9067 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6063 0.7436 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6821 0.1225 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1510 0.6278 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7554 2.1682 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6066 -2.6596 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9680 1.6767 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5747 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8193 -3.1511 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.9830 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8193 2.1682 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 4.6066 1.6767 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 3.7554 -3.1511 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 5.5747 -0.9830 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.9680 -2.6596 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.6343 0.5971 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.0916 3.0919 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.2385 -3.4126 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.3362 2.4297 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.5427 0.1707 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4831 -4.0748 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9680 -1.1537 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 10.3461 0.0593 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.0412 -0.7926 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4731 -0.0956 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4 45 1 0 0 0 0 5 46 1 0 0 0 0 6 47 1 0 0 0 0 7 55 1 0 0 0 0 8 56 1 0 0 0 0 9 13 1 0 0 0 0 9 25 2 0 0 0 0 10 14 2 0 0 0 0 10 25 1 0 0 0 0 11 15 1 0 0 0 0 11 26 2 0 0 0 0 12 16 2 0 0 0 0 12 26 1 0 0 0 0 13 28 2 0 0 0 0 14 28 1 0 0 0 0 15 29 2 0 0 0 0 16 29 1 0 0 0 0 17 25 1 0 0 0 0 18 26 1 0 0 0 0 19 27 1 0 0 0 0 20 27 2 0 0 0 0 20 35 1 0 0 0 0 21 33 2 0 0 0 0 21 34 1 0 0 0 0 22 1 1 6 0 0 0 22 36 1 0 0 0 0 22 42 1 0 0 0 0 23 2 1 1 0 0 0 23 39 1 0 0 0 0 23 43 1 0 0 0 0 24 3 1 1 0 0 0 24 40 1 0 0 0 0 24 44 1 0 0 0 0 27 33 1 0 0 0 0 28 55 1 0 0 0 0 29 57 1 0 0 0 0 30 17 1 1 0 0 0 30 37 1 0 0 0 0 30 45 1 0 0 0 0 31 19 1 1 0 0 0 31 38 1 0 0 0 0 31 46 1 0 0 0 0 32 18 1 1 0 0 0 32 41 1 0 0 0 0 32 47 1 0 0 0 0 33 48 1 0 0 0 0 34 35 2 0 0 0 0 34 56 1 0 0 0 0 35 57 1 0 0 0 0 36 43 2 3 0 0 0 36 49 1 0 0 0 0 37 44 2 3 0 0 0 37 50 1 0 0 0 0 38 42 2 3 0 0 0 38 51 1 0 0 0 0 39 45 1 0 0 0 0 39 52 2 0 0 0 0 40 47 1 0 0 0 0 40 53 2 0 0 0 0 41 46 1 0 0 0 0 41 54 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	786.36
Volume:	789.246
LogP:	2.004
LogD:	1.772
LogS:	-3.465
# Rotatable Bonds:	4
TPSA:	196.15
# H-Bond Aceptor:	16
# H-Bond Donor:	4
# Rings:	6
# Heavy Atoms:	16

MedChem Properties

QED Drug-Likeness Score:	0.302
Synthetic Accessibility Score:	6.611
Fsp3:	0.415
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.554
MDCK Permeability:	1.4848704267933499e-05
Pgp-inhibitor:	1.0
Pgp-substrate:	0.854
Human Intestinal Absorption (HIA):	0.228
20% Bioavailability (F20%):	0.08
30% Bioavailability (F30%):	0.692

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.061
Plasma Protein Binding (PPB):	74.17516326904297%
Volume Distribution (VD):	0.336
Pgp-substrate:	17.50629234313965%

ADMET: Metabolism

CYP1A2-inhibitor:	0.002
CYP1A2-substrate:	0.052
CYP2C19-inhibitor:	0.123
CYP2C19-substrate:	0.081
CYP2C9-inhibitor:	0.231
CYP2C9-substrate:	0.069
CYP2D6-inhibitor:	0.024
CYP2D6-substrate:	0.299
CYP3A4-inhibitor:	0.908
CYP3A4-substrate:	0.122

ADMET: Excretion

Clearance (CL):	9.2
Half-life (T1/2):	0.25

ADMET: Toxicity

hERG Blockers:	0.021
Human Hepatotoxicity (H-HT):	0.982
Drug-inuced Liver Injury (DILI):	0.952
AMES Toxicity:	0.021
Rat Oral Acute Toxicity:	0.435
Maximum Recommended Daily Dose:	0.932
Skin Sensitization:	0.036
Carcinogencity:	0.015
Eye Corrosion:	0.003
Eye Irritation:	0.004
Respiratory Toxicity:	0.283

Download Data

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

Natural Product: NPC471563

Natural Product ID:	NPC471563
*Common Name:**	SGOGBYJZVOEWDW-LZQLRFBTSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	SGOGBYJZVOEWDW-LZQLRFBTSA-N
Standard InCHI:	InChI=1S/C41H50N6O10/c1-22-36(49)43-23(2)39(52)45(4)30(17-25-9-13-28(55-7)14-10-25)37(50)44-24(3)40(53)47(6)32-18-26-11-15-29(16-12-26)57-35-20-27(33(48)21-34(35)56-8)19-31(38(51)42-22)46(5)41(32)54/h9-16,20-24,30-32,48H,17-19H2,1-8H3,(H,42,51)(H,43,49)(H,44,50)/t22-,23+,24+,30+,31+,32+/m1/s1
SMILES:	COc1ccc(cc1)C[C@H]1C(=N[C@@H](C)C(=O)N(C)[C@H]2Cc3ccc(cc3)Oc3cc(C[C@H](N(C2=O)C)C(=N[C@@H](C(=N[C@H](C(=O)N1C)C)O)C)O)c(O)cc3OC)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL257622
PubChem CID:	44455329
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0001392] Lignans, neolignans and related compounds

*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
NPO26542	Rubia cordifolia	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18078747]
NPO26542	Rubia cordifolia	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8882438]
NPO26542	Rubia cordifolia	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26542	Rubia cordifolia	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26542	Rubia cordifolia	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO26542	Rubia cordifolia	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO26542	Rubia cordifolia	Species	Rubiaceae	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	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT168	Cell Line	P388	Mus musculus	IC50	=	0.093	ug.mL-1	PMID[533788]

☑ 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 NPC471563 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	308
0.1-0.2	1503
0.2-0.3	7777
0.3-0.4	10280
0.4-0.5	5612
0.5-0.6	9444
0.6-0.7	7411
0.7-0.8	345
0.8-0.85	4
0.85-0.9	9
0.9-0.95	2
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.954	High Similarity	NPC29531
0.908	High Similarity	NPC32064
0.907	High Similarity	NPC164608
0.8983	High Similarity	NPC138083
0.8859	High Similarity	NPC50548
0.8827	High Similarity	NPC276120
0.8804	High Similarity	NPC144314
0.8785	High Similarity	NPC64140
0.8785	High Similarity	NPC174122
0.875	High Similarity	NPC149962
0.8729	High Similarity	NPC234069
0.8663	High Similarity	NPC242728
0.861	High Similarity	NPC123859
0.8051	Intermediate Similarity	NPC473460
0.7927	Intermediate Similarity	NPC281629
0.7919	Intermediate Similarity	NPC473422
0.785	Intermediate Similarity	NPC471561
0.7812	Intermediate Similarity	NPC41122
0.7812	Intermediate Similarity	NPC318805
0.7806	Intermediate Similarity	NPC469689
0.7806	Intermediate Similarity	NPC471031
0.776	Intermediate Similarity	NPC473407
0.776	Intermediate Similarity	NPC473378
0.7749	Intermediate Similarity	NPC116465
0.7749	Intermediate Similarity	NPC212237
0.7707	Intermediate Similarity	NPC471531
0.7692	Intermediate Similarity	NPC179250
0.7692	Intermediate Similarity	NPC50380
0.7685	Intermediate Similarity	NPC471532
0.7684	Intermediate Similarity	NPC315542
0.7684	Intermediate Similarity	NPC30779
0.7656	Intermediate Similarity	NPC470846
0.7654	Intermediate Similarity	NPC475557
0.7653	Intermediate Similarity	NPC234318
0.765	Intermediate Similarity	NPC477666
0.7647	Intermediate Similarity	NPC232386
0.7647	Intermediate Similarity	NPC152680
0.7647	Intermediate Similarity	NPC190783
0.7641	Intermediate Similarity	NPC85381
0.764	Intermediate Similarity	NPC127402
0.7634	Intermediate Similarity	NPC159767
0.7634	Intermediate Similarity	NPC155506
0.7633	Intermediate Similarity	NPC82056
0.7632	Intermediate Similarity	NPC286119
0.7632	Intermediate Similarity	NPC195538
0.7626	Intermediate Similarity	NPC475654
0.7621	Intermediate Similarity	NPC38964
0.7619	Intermediate Similarity	NPC475349
0.7619	Intermediate Similarity	NPC475292
0.7619	Intermediate Similarity	NPC475565
0.7611	Intermediate Similarity	NPC319320
0.7611	Intermediate Similarity	NPC287757
0.7604	Intermediate Similarity	NPC16357
0.7604	Intermediate Similarity	NPC95426
0.7604	Intermediate Similarity	NPC302245
0.7596	Intermediate Similarity	NPC254700
0.7592	Intermediate Similarity	NPC290582
0.7592	Intermediate Similarity	NPC185639
0.7592	Intermediate Similarity	NPC42663
0.7592	Intermediate Similarity	NPC251735
0.7592	Intermediate Similarity	NPC328155
0.7592	Intermediate Similarity	NPC104196
0.7592	Intermediate Similarity	NPC222661
0.7592	Intermediate Similarity	NPC7715
0.7592	Intermediate Similarity	NPC54654
0.7592	Intermediate Similarity	NPC311973
0.7592	Intermediate Similarity	NPC290005
0.7592	Intermediate Similarity	NPC217748
0.7592	Intermediate Similarity	NPC90998
0.7592	Intermediate Similarity	NPC239824
0.7592	Intermediate Similarity	NPC8836
0.7592	Intermediate Similarity	NPC182052
0.7592	Intermediate Similarity	NPC285931
0.7592	Intermediate Similarity	NPC49075
0.7592	Intermediate Similarity	NPC258657
0.7592	Intermediate Similarity	NPC181796
0.7592	Intermediate Similarity	NPC15414
0.7592	Intermediate Similarity	NPC223690
0.7592	Intermediate Similarity	NPC229373
0.7592	Intermediate Similarity	NPC279228
0.7592	Intermediate Similarity	NPC271013
0.7592	Intermediate Similarity	NPC476202
0.7583	Intermediate Similarity	NPC475624
0.7571	Intermediate Similarity	NPC233702
0.7566	Intermediate Similarity	NPC293093
0.7565	Intermediate Similarity	NPC65312
0.7565	Intermediate Similarity	NPC139783
0.7556	Intermediate Similarity	NPC56635
0.7552	Intermediate Similarity	NPC274716
0.7552	Intermediate Similarity	NPC254441
0.7552	Intermediate Similarity	NPC167116
0.754	Intermediate Similarity	NPC476227
0.754	Intermediate Similarity	NPC473402
0.7536	Intermediate Similarity	NPC475442
0.7527	Intermediate Similarity	NPC230611
0.7526	Intermediate Similarity	NPC22115
0.7526	Intermediate Similarity	NPC275680
0.7526	Intermediate Similarity	NPC329816
0.7514	Intermediate Similarity	NPC107602
0.7513	Intermediate Similarity	NPC249996
0.7487	Intermediate Similarity	NPC83198
0.7487	Intermediate Similarity	NPC204908
0.7487	Intermediate Similarity	NPC306804
0.7459	Intermediate Similarity	NPC107938
0.7459	Intermediate Similarity	NPC294516
0.7459	Intermediate Similarity	NPC328649
0.7458	Intermediate Similarity	NPC473934
0.7449	Intermediate Similarity	NPC473716
0.7449	Intermediate Similarity	NPC475597
0.7448	Intermediate Similarity	NPC294951
0.7447	Intermediate Similarity	NPC26108
0.7447	Intermediate Similarity	NPC473354
0.7443	Intermediate Similarity	NPC16188
0.7421	Intermediate Similarity	NPC45037
0.7415	Intermediate Similarity	NPC293347
0.7407	Intermediate Similarity	NPC276890
0.7407	Intermediate Similarity	NPC317145
0.7407	Intermediate Similarity	NPC227060
0.7407	Intermediate Similarity	NPC76682
0.7407	Intermediate Similarity	NPC198498
0.7407	Intermediate Similarity	NPC317439
0.7407	Intermediate Similarity	NPC63646
0.7407	Intermediate Similarity	NPC115284
0.7407	Intermediate Similarity	NPC10908
0.7402	Intermediate Similarity	NPC79130
0.7402	Intermediate Similarity	NPC258128
0.7398	Intermediate Similarity	NPC82457
0.7398	Intermediate Similarity	NPC206900
0.7398	Intermediate Similarity	NPC274661
0.7398	Intermediate Similarity	NPC175890
0.7398	Intermediate Similarity	NPC11296
0.7398	Intermediate Similarity	NPC48490
0.7396	Intermediate Similarity	NPC471526
0.7395	Intermediate Similarity	NPC470847
0.7394	Intermediate Similarity	NPC273755
0.7394	Intermediate Similarity	NPC137627
0.7386	Intermediate Similarity	NPC472332
0.7386	Intermediate Similarity	NPC472335
0.738	Intermediate Similarity	NPC90984
0.738	Intermediate Similarity	NPC196091
0.738	Intermediate Similarity	NPC40234
0.7379	Intermediate Similarity	NPC14390
0.7376	Intermediate Similarity	NPC311357
0.7374	Intermediate Similarity	NPC478092
0.7374	Intermediate Similarity	NPC473589
0.7374	Intermediate Similarity	NPC30182
0.7374	Intermediate Similarity	NPC256124
0.7374	Intermediate Similarity	NPC478091
0.7368	Intermediate Similarity	NPC12424
0.7368	Intermediate Similarity	NPC41376
0.7368	Intermediate Similarity	NPC251580
0.7368	Intermediate Similarity	NPC129518
0.736	Intermediate Similarity	NPC191132
0.736	Intermediate Similarity	NPC60295
0.7354	Intermediate Similarity	NPC279871
0.7354	Intermediate Similarity	NPC471165
0.735	Intermediate Similarity	NPC83019
0.7349	Intermediate Similarity	NPC5674
0.7347	Intermediate Similarity	NPC283207
0.734	Intermediate Similarity	NPC235698
0.7337	Intermediate Similarity	NPC308709
0.7333	Intermediate Similarity	NPC202198
0.733	Intermediate Similarity	NPC475421
0.733	Intermediate Similarity	NPC194671
0.733	Intermediate Similarity	NPC269750
0.7323	Intermediate Similarity	NPC24260
0.7323	Intermediate Similarity	NPC478093
0.7318	Intermediate Similarity	NPC324081
0.7318	Intermediate Similarity	NPC115144
0.7318	Intermediate Similarity	NPC277857
0.7316	Intermediate Similarity	NPC50016
0.7308	Intermediate Similarity	NPC477665
0.7304	Intermediate Similarity	NPC169605
0.7303	Intermediate Similarity	NPC5462
0.7303	Intermediate Similarity	NPC9373
0.7302	Intermediate Similarity	NPC473748
0.73	Intermediate Similarity	NPC204580
0.7297	Intermediate Similarity	NPC329837
0.7296	Intermediate Similarity	NPC47077
0.7296	Intermediate Similarity	NPC124626
0.7296	Intermediate Similarity	NPC14507
0.7287	Intermediate Similarity	NPC471568
0.7287	Intermediate Similarity	NPC13916
0.7287	Intermediate Similarity	NPC473693
0.7287	Intermediate Similarity	NPC474858
0.7287	Intermediate Similarity	NPC264850
0.7278	Intermediate Similarity	NPC471032
0.7278	Intermediate Similarity	NPC470935
0.7273	Intermediate Similarity	NPC141957
0.7259	Intermediate Similarity	NPC163961
0.7259	Intermediate Similarity	NPC208890
0.7259	Intermediate Similarity	NPC473305
0.7258	Intermediate Similarity	NPC472923
0.7257	Intermediate Similarity	NPC296898
0.7254	Intermediate Similarity	NPC476321
0.7249	Intermediate Similarity	NPC89831
0.7234	Intermediate Similarity	NPC186617
0.7234	Intermediate Similarity	NPC24465
0.7225	Intermediate Similarity	NPC231371
0.7219	Intermediate Similarity	NPC304074

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 NPC471563 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	183
0.1-0.2	589
0.2-0.3	1233
0.3-0.4	2147
0.4-0.5	2460
0.5-0.6	1860
0.6-0.7	623
0.7-0.8	55
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
0.7861	Intermediate Similarity	NPD7132	Clinical (unspecified phase)
0.7784	Intermediate Similarity	NPD7667	Clinical (unspecified phase)
0.7727	Intermediate Similarity	NPD7131	Phase 3
0.7667	Intermediate Similarity	NPD5772	Approved
0.7667	Intermediate Similarity	NPD5773	Approved
0.7663	Intermediate Similarity	NPD7608	Discontinued
0.765	Intermediate Similarity	NPD5677	Discontinued
0.7644	Intermediate Similarity	NPD2219	Phase 1
0.7637	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7626	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7598	Intermediate Similarity	NPD4678	Approved
0.7598	Intermediate Similarity	NPD4675	Approved
0.7592	Intermediate Similarity	NPD8053	Approved
0.7592	Intermediate Similarity	NPD6851	Approved
0.7592	Intermediate Similarity	NPD8054	Approved
0.7592	Intermediate Similarity	NPD6853	Approved
0.7566	Intermediate Similarity	NPD6297	Approved
0.7419	Intermediate Similarity	NPD7485	Phase 3
0.7419	Intermediate Similarity	NPD7484	Phase 3
0.7407	Intermediate Similarity	NPD8252	Approved
0.7407	Intermediate Similarity	NPD8099	Discontinued
0.7407	Intermediate Similarity	NPD8251	Approved
0.7385	Intermediate Similarity	NPD7906	Approved
0.7377	Intermediate Similarity	NPD6818	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD8156	Discontinued
0.7366	Intermediate Similarity	NPD6746	Phase 2
0.7347	Intermediate Similarity	NPD6377	Clinical (unspecified phase)
0.732	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7318	Intermediate Similarity	NPD4123	Phase 3
0.7308	Intermediate Similarity	NPD7827	Phase 1
0.7297	Intermediate Similarity	NPD6788	Approved
0.7283	Intermediate Similarity	NPD6668	Clinical (unspecified phase)
0.7268	Intermediate Similarity	NPD7280	Phase 3
0.7268	Intermediate Similarity	NPD7281	Phase 3
0.7254	Intermediate Similarity	NPD7039	Approved
0.7254	Intermediate Similarity	NPD7038	Approved
0.7241	Intermediate Similarity	NPD2494	Approved
0.7241	Intermediate Similarity	NPD2493	Approved
0.7228	Intermediate Similarity	NPD7810	Phase 3
0.7228	Intermediate Similarity	NPD7811	Phase 3
0.7222	Intermediate Similarity	NPD7447	Phase 1
0.7222	Intermediate Similarity	NPD5525	Clinical (unspecified phase)
0.7216	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7216	Intermediate Similarity	NPD7549	Discontinued
0.7214	Intermediate Similarity	NPD2974	Approved
0.7214	Intermediate Similarity	NPD2975	Approved
0.7214	Intermediate Similarity	NPD2973	Approved
0.7189	Intermediate Similarity	NPD7046	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD6042	Phase 2
0.7188	Intermediate Similarity	NPD42	Phase 2
0.7174	Intermediate Similarity	NPD6072	Discontinued
0.7158	Intermediate Similarity	NPD7261	Clinical (unspecified phase)
0.7158	Intermediate Similarity	NPD4005	Discontinued
0.7157	Intermediate Similarity	NPD3452	Approved
0.7157	Intermediate Similarity	NPD3450	Approved
0.7143	Intermediate Similarity	NPD6662	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD2122	Discontinued
0.7136	Intermediate Similarity	NPD4582	Approved
0.7136	Intermediate Similarity	NPD4583	Approved
0.7123	Intermediate Similarity	NPD7047	Phase 3
0.7108	Intermediate Similarity	NPD4580	Approved
0.709	Intermediate Similarity	NPD7201	Clinical (unspecified phase)
0.7087	Intermediate Similarity	NPD4002	Approved
0.7087	Intermediate Similarity	NPD4004	Approved
0.7085	Intermediate Similarity	NPD7861	Discontinued
0.7081	Intermediate Similarity	NPD6385	Approved
0.7081	Intermediate Similarity	NPD7109	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD7118	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD7110	Phase 1
0.7081	Intermediate Similarity	NPD6386	Approved
0.7079	Intermediate Similarity	NPD7596	Clinical (unspecified phase)
0.7074	Intermediate Similarity	NPD4055	Discovery
0.7072	Intermediate Similarity	NPD7213	Phase 3
0.7072	Intermediate Similarity	NPD7212	Phase 2
0.7072	Intermediate Similarity	NPD4357	Discontinued
0.7072	Intermediate Similarity	NPD5297	Approved
0.7071	Intermediate Similarity	NPD4663	Approved
0.7068	Intermediate Similarity	NPD5137	Approved
0.7056	Intermediate Similarity	NPD3692	Discontinued
0.7056	Intermediate Similarity	NPD5241	Discontinued
0.7043	Intermediate Similarity	NPD7945	Clinical (unspecified phase)
0.7035	Intermediate Similarity	NPD7291	Discontinued
0.7033	Intermediate Similarity	NPD1754	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD6312	Discontinued
0.7017	Intermediate Similarity	NPD7124	Phase 2
0.7005	Intermediate Similarity	NPD4577	Approved
0.7005	Intermediate Similarity	NPD4578	Approved
0.7005	Intermediate Similarity	NPD2801	Approved
0.7005	Intermediate Similarity	NPD6997	Phase 2
0.7	Intermediate Similarity	NPD8153	Approved
0.7	Intermediate Similarity	NPD8152	Approved
0.6986	Remote Similarity	NPD7263	Phase 2
0.6979	Remote Similarity	NPD8051	Clinical (unspecified phase)
0.6965	Remote Similarity	NPD3808	Clinical (unspecified phase)
0.6965	Remote Similarity	NPD2490	Approved
0.6965	Remote Similarity	NPD2488	Approved
0.6961	Remote Similarity	NPD5307	Clinical (unspecified phase)
0.6961	Remote Similarity	NPD6621	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD5718	Phase 2
0.6952	Remote Similarity	NPD7585	Approved
0.695	Remote Similarity	NPD7243	Clinical (unspecified phase)
0.695	Remote Similarity	NPD4157	Discontinued
0.6944	Remote Similarity	NPD3060	Approved
0.694	Remote Similarity	NPD3688	Clinical (unspecified phase)
0.694	Remote Similarity	NPD3146	Approved
0.6938	Remote Similarity	NPD7607	Clinical (unspecified phase)
0.6936	Remote Similarity	NPD5752	Clinical (unspecified phase)
0.6935	Remote Similarity	NPD6875	Approved
0.6935	Remote Similarity	NPD6876	Approved
0.6919	Remote Similarity	NPD3686	Approved
0.6919	Remote Similarity	NPD3687	Approved
0.6905	Remote Similarity	NPD7584	Approved
0.6905	Remote Similarity	NPD7583	Approved
0.6902	Remote Similarity	NPD52	Approved
0.6902	Remote Similarity	NPD7526	Approved
0.6902	Remote Similarity	NPD7527	Clinical (unspecified phase)
0.6898	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6891	Remote Similarity	NPD5242	Approved
0.6884	Remote Similarity	NPD8149	Discontinued
0.6882	Remote Similarity	NPD8158	Clinical (unspecified phase)
0.6878	Remote Similarity	NPD5967	Approved
0.6875	Remote Similarity	NPD5006	Approved
0.6875	Remote Similarity	NPD5005	Approved
0.6872	Remote Similarity	NPD7450	Phase 2
0.6866	Remote Similarity	NPD8318	Clinical (unspecified phase)
0.6866	Remote Similarity	NPD4435	Approved
0.6863	Remote Similarity	NPD4413	Clinical (unspecified phase)
0.6851	Remote Similarity	NPD4236	Phase 3
0.6851	Remote Similarity	NPD4237	Approved
0.6848	Remote Similarity	NPD1424	Approved
0.6845	Remote Similarity	NPD6502	Phase 2
0.6839	Remote Similarity	NPD2517	Approved
0.6839	Remote Similarity	NPD3051	Approved
0.6834	Remote Similarity	NPD7311	Approved
0.6834	Remote Similarity	NPD7312	Approved
0.6834	Remote Similarity	NPD7313	Approved
0.6834	Remote Similarity	NPD7310	Approved
0.6834	Remote Similarity	NPD2968	Approved
0.6834	Remote Similarity	NPD2971	Approved
0.6833	Remote Similarity	NPD7223	Discontinued
0.6833	Remote Similarity	NPD7224	Discontinued
0.6831	Remote Similarity	NPD6666	Approved
0.6831	Remote Similarity	NPD6667	Approved
0.6829	Remote Similarity	NPD4361	Phase 2
0.6829	Remote Similarity	NPD4362	Clinical (unspecified phase)
0.6825	Remote Similarity	NPD2978	Approved
0.6825	Remote Similarity	NPD6973	Clinical (unspecified phase)
0.6825	Remote Similarity	NPD2977	Approved
0.6818	Remote Similarity	NPD5745	Approved
0.6816	Remote Similarity	NPD4434	Approved
0.6812	Remote Similarity	NPD7237	Clinical (unspecified phase)
0.6809	Remote Similarity	NPD5089	Approved
0.6809	Remote Similarity	NPD5090	Approved
0.6806	Remote Similarity	NPD8031	Discontinued
0.6806	Remote Similarity	NPD8070	Approved
0.6806	Remote Similarity	NPD6971	Discontinued
0.6804	Remote Similarity	NPD2970	Approved
0.6804	Remote Similarity	NPD2969	Approved
0.6804	Remote Similarity	NPD7907	Approved
0.6802	Remote Similarity	NPD8059	Phase 3
0.6802	Remote Similarity	NPD8058	Clinical (unspecified phase)
0.68	Remote Similarity	NPD7309	Approved
0.6796	Remote Similarity	NPD7153	Discontinued
0.6791	Remote Similarity	NPD824	Approved
0.6788	Remote Similarity	NPD2516	Approved
0.6786	Remote Similarity	NPD5940	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD7177	Discontinued
0.678	Remote Similarity	NPD3473	Clinical (unspecified phase)
0.6777	Remote Similarity	NPD8161	Suspended
0.6772	Remote Similarity	NPD8019	Approved
0.6772	Remote Similarity	NPD1934	Approved
0.6771	Remote Similarity	NPD8245	Clinical (unspecified phase)
0.6769	Remote Similarity	NPD2489	Approved
0.6769	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6769	Remote Similarity	NPD6166	Phase 2
0.6769	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6769	Remote Similarity	NPD5822	Clinical (unspecified phase)
0.6769	Remote Similarity	NPD27	Approved
0.6763	Remote Similarity	NPD4420	Approved
0.6758	Remote Similarity	NPD6860	Clinical (unspecified phase)
0.6758	Remote Similarity	NPD4162	Approved
0.6758	Remote Similarity	NPD5177	Phase 3
0.6757	Remote Similarity	NPD3158	Phase 1
0.6757	Remote Similarity	NPD3157	Approved
0.6754	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6753	Remote Similarity	NPD6071	Discontinued
0.6751	Remote Similarity	NPD5313	Approved
0.6751	Remote Similarity	NPD5312	Approved
0.6738	Remote Similarity	NPD4210	Discontinued
0.6737	Remote Similarity	NPD7972	Discontinued
0.6734	Remote Similarity	NPD5192	Clinical (unspecified phase)
0.6731	Remote Similarity	NPD8095	Phase 1
0.673	Remote Similarity	NPD4040	Phase 1
0.6723	Remote Similarity	NPD7477	Discontinued
0.6723	Remote Similarity	NPD2674	Phase 3
0.6722	Remote Similarity	NPD6029	Clinical (unspecified phase)
0.6722	Remote Similarity	NPD6028	Clinical (unspecified phase)
0.6721	Remote Similarity	NPD6331	Phase 2
0.6721	Remote Similarity	NPD6658	Clinical (unspecified phase)
0.6721	Remote Similarity	NPD7466	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