NPASS Compound

Structure

NPC476210 OpenBabel07101718272D 47 52 0 0 1 0 0 0 0 0999 V2000 2.0338 -3.1641 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4581 -2.3418 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2109 -2.8486 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4337 -2.8486 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1482 3.9685 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3272 -1.1641 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5591 -1.7222 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5590 -0.6971 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5086 -0.6971 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0338 -1.5194 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3886 -1.4243 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4337 -0.9495 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0666 2.3259 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8674 0.5008 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0338 0.1252 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0843 0.3756 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5000 1.4811 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0767 -0.4272 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5086 -2.3418 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3886 -2.3738 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5816 3.1237 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6506 0.3756 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4337 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1685 0.2504 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.5103 -0.7779 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.2169 0.3756 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2169 0.3756 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 0.4337 0.5008 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0213 0.4530 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 0.0000 0.5008 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6506 0.1252 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2169 0.1252 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3040 0.7446 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5300 3.0766 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4598 -0.7779 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0843 0.1252 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -0.9850 0.6833 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.2169 0.1252 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.4337 1.4503 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.6081 2.2591 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 2.3999 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0296 1.6336 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.0449 3.8743 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.9633 2.2317 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8674 -0.0000 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 -1.7532 0.1252 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 19 1 0 0 0 0 2 19 1 0 0 0 0 3 20 1 0 0 0 0 4 20 1 0 0 0 0 5 21 1 0 0 0 0 6 35 1 0 0 0 0 7 35 1 0 0 0 0 8 36 1 0 0 0 0 9 10 1 0 0 0 0 9 15 1 0 0 0 0 10 19 2 0 0 0 0 11 12 1 0 0 0 0 11 20 2 0 0 0 0 12 23 1 0 0 0 0 13 17 1 0 0 0 0 13 21 2 0 0 0 0 14 16 2 0 0 0 0 14 22 1 0 0 0 0 15 36 1 0 0 0 0 16 36 1 0 0 0 0 17 37 1 0 0 0 0 18 25 1 0 0 0 0 21 34 1 0 0 0 0 22 28 2 0 0 0 0 22 31 1 0 0 0 0 23 31 2 0 0 0 0 23 32 1 0 0 0 0 24 18 1 6 0 0 0 24 29 1 0 0 0 0 24 33 1 0 0 0 0 25 35 1 0 0 0 0 25 38 1 6 0 0 0 26 28 1 0 0 0 0 26 30 1 0 0 0 0 26 32 2 0 0 0 0 27 29 1 0 0 0 0 27 30 1 0 0 0 0 27 38 1 0 0 0 0 28 39 1 0 0 0 0 29 40 1 0 0 0 0 30 41 2 0 0 0 0 31 45 1 0 0 0 0 32 46 1 0 0 0 0 33 37 1 0 0 0 0 33 42 2 0 0 0 0 34 43 2 0 0 0 0 34 44 1 0 0 0 0 35 47 1 0 0 0 0 36 45 1 0 0 0 0 37 38 1 6 0 0 0 37 47 1 0 0 0 0 38 46 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	646.31
Volume:	667.213
LogP:	7.453
LogD:	3.707
LogS:	-2.924
# Rotatable Bonds:	8
TPSA:	139.59
# H-Bond Aceptor:	9
# H-Bond Donor:	3
# Rings:	7
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.284
Synthetic Accessibility Score:	7.193
Fsp3:	0.553
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:	-5.071
MDCK Permeability:	1.6595315173617564e-05
Pgp-inhibitor:	0.651
Pgp-substrate:	0.889
Human Intestinal Absorption (HIA):	0.678
20% Bioavailability (F20%):	0.057
30% Bioavailability (F30%):	0.463

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.355
Plasma Protein Binding (PPB):	84.00198364257812%
Volume Distribution (VD):	1.426
Pgp-substrate:	9.933197021484375%

ADMET: Metabolism

CYP1A2-inhibitor:	0.02
CYP1A2-substrate:	0.184
CYP2C19-inhibitor:	0.015
CYP2C19-substrate:	0.59
CYP2C9-inhibitor:	0.045
CYP2C9-substrate:	0.227
CYP2D6-inhibitor:	0.026
CYP2D6-substrate:	0.065
CYP3A4-inhibitor:	0.499
CYP3A4-substrate:	0.289

ADMET: Excretion

Clearance (CL):	1.767
Half-life (T1/2):	0.016

ADMET: Toxicity

hERG Blockers:	0.037
Human Hepatotoxicity (H-HT):	0.96
Drug-inuced Liver Injury (DILI):	0.964
AMES Toxicity:	0.004
Rat Oral Acute Toxicity:	0.985
Maximum Recommended Daily Dose:	0.744
Skin Sensitization:	0.085
Carcinogencity:	0.724
Eye Corrosion:	0.003
Eye Irritation:	0.006
Respiratory Toxicity:	0.969

Download Data

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

Natural Product: NPC476210

Natural Product ID:	NPC476210
*Common Name:**	LJUARHDVFLLQMF-KELXBUOKSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	LJUARHDVFLLQMF-KELXBUOKSA-N
Standard InCHI:	InChI=1S/C38H46O9/c1-19(2)10-9-15-36(8)16-14-22-28(39)26-30(41)27-29(40)24-18-25-35(6,7)47-37(33(24)42,17-13-21(5)34(43)44)38(25,27)46-32(26)23(31(22)45-36)12-11-20(3)4/h10-11,13-14,16,24-25,27,29,39-40H,9,12,15,17-18H2,1-8H3,(H,43,44)/b21-13-/t24-,25-,27?,29?,36?,37-,38-/m0/s1
SMILES:	CC(=CCc1c2O[C@]34C(C(=O)c2c(c2c1OC(C)(CCC=C(C)C)C=C2)O)C(O)[C@@H]1C[C@H]3C(O[C@@]4(C/C=C(C(=O)O)/C)C1=O)(C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL554099
PubChem CID:	45272281
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000123] Benzopyrans [CHEMONTID:0003410] 1-benzopyrans [CHEMONTID:0002817] Dibenzopyrans [CHEMONTID:0000200] Xanthenes [CHEMONTID:0000204] Xanthones [CHEMONTID:0003521] Pyranoxanthones

*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
NPO13310	Garcinia hanburyi	Species	Clusiaceae	Eukaryota	n.a.	latex	n.a.	PMID[17117343]
NPO13310	Garcinia hanburyi	Species	Clusiaceae	Eukaryota	n.a.	fruit	n.a.	PMID[17117343]
NPO13310	Garcinia hanburyi	Species	Clusiaceae	Eukaryota	resin	n.a.	n.a.	PMID[19072548]
NPO13310	Garcinia hanburyi	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21486005]
NPO13310	Garcinia hanburyi	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13310	Garcinia hanburyi	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO13310	Garcinia hanburyi	Species	Clusiaceae	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	2

Activity Type	# Activity
Cell Line	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT165	Cell Line	HeLa	Homo sapiens	IC50	=	640.0	nM	PMID[549107]
NPT165	Cell Line	HeLa	Homo sapiens	IC50	=	630.0	nM	PMID[549108]

☑ 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 NPC476210 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	397
0.1-0.2	1530
0.2-0.3	3139
0.3-0.4	6206
0.4-0.5	10151
0.5-0.6	7743
0.6-0.7	5875
0.7-0.8	7222
0.8-0.85	353
0.85-0.9	47
0.9-0.95	27
0.95-1	7

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC476199
0.9817	High Similarity	NPC476311
0.9697	High Similarity	NPC476152
0.9695	High Similarity	NPC476196
0.9583	High Similarity	NPC473729
0.9578	High Similarity	NPC476229
0.9518	High Similarity	NPC476159
0.9515	High Similarity	NPC102810
0.9515	High Similarity	NPC158329
0.9515	High Similarity	NPC40089
0.9515	High Similarity	NPC476146
0.9467	High Similarity	NPC473607
0.9461	High Similarity	NPC476139
0.9405	High Similarity	NPC162248
0.9398	High Similarity	NPC63514
0.9398	High Similarity	NPC75141
0.9398	High Similarity	NPC47634
0.9398	High Similarity	NPC55422
0.9398	High Similarity	NPC41598
0.9349	High Similarity	NPC227275
0.9337	High Similarity	NPC223413
0.9294	High Similarity	NPC233978
0.9281	High Similarity	NPC476216
0.9217	High Similarity	NPC189689
0.9172	High Similarity	NPC118128
0.9157	High Similarity	NPC131578
0.9123	High Similarity	NPC98943
0.9064	High Similarity	NPC475398
0.9059	High Similarity	NPC169018
0.8976	High Similarity	NPC286422
0.8935	High Similarity	NPC476255
0.8935	High Similarity	NPC62444
0.8857	High Similarity	NPC208069
0.8837	High Similarity	NPC477529
0.8817	High Similarity	NPC476931
0.8793	High Similarity	NPC469345
0.8786	High Similarity	NPC469393
0.8786	High Similarity	NPC475080
0.8779	High Similarity	NPC193698
0.8772	High Similarity	NPC193222
0.8765	High Similarity	NPC473908
0.8757	High Similarity	NPC106700
0.8757	High Similarity	NPC94796
0.8736	High Similarity	NPC232412
0.8736	High Similarity	NPC86809
0.8736	High Similarity	NPC294149
0.8736	High Similarity	NPC98667
0.8721	High Similarity	NPC286074
0.8721	High Similarity	NPC54903
0.8713	High Similarity	NPC476056
0.8701	High Similarity	NPC475148
0.8701	High Similarity	NPC475656
0.8698	High Similarity	NPC476929
0.8671	High Similarity	NPC251144
0.8671	High Similarity	NPC241387
0.8659	High Similarity	NPC282636
0.8659	High Similarity	NPC294863
0.8639	High Similarity	NPC43490
0.8639	High Similarity	NPC475107
0.8631	High Similarity	NPC476930
0.8621	High Similarity	NPC472620
0.8613	High Similarity	NPC207574
0.8613	High Similarity	NPC291795
0.8613	High Similarity	NPC297195
0.8613	High Similarity	NPC217378
0.8605	High Similarity	NPC17274
0.8605	High Similarity	NPC85047
0.8605	High Similarity	NPC469394
0.8605	High Similarity	NPC120857
0.8596	High Similarity	NPC469395
0.8588	High Similarity	NPC244903
0.8588	High Similarity	NPC97812
0.8588	High Similarity	NPC92589
0.8588	High Similarity	NPC472346
0.858	High Similarity	NPC324220
0.858	High Similarity	NPC125969
0.858	High Similarity	NPC312630
0.8579	High Similarity	NPC282474
0.8579	High Similarity	NPC316274
0.8579	High Similarity	NPC470196
0.8579	High Similarity	NPC470198
0.8579	High Similarity	NPC470193
0.8579	High Similarity	NPC470194
0.8579	High Similarity	NPC470195
0.8579	High Similarity	NPC470197
0.8579	High Similarity	NPC470200
0.8571	High Similarity	NPC164427
0.8571	High Similarity	NPC73899
0.8571	High Similarity	NPC474276
0.8571	High Similarity	NPC17105
0.8571	High Similarity	NPC147363
0.8564	High Similarity	NPC314672
0.8555	High Similarity	NPC472622
0.8554	High Similarity	NPC476162
0.8538	High Similarity	NPC475106
0.8531	High Similarity	NPC477683
0.8531	High Similarity	NPC477682
0.8529	High Similarity	NPC472055
0.8525	High Similarity	NPC314020
0.8514	High Similarity	NPC473113
0.8514	High Similarity	NPC121333
0.8506	High Similarity	NPC473095
0.8506	High Similarity	NPC20734
0.8506	High Similarity	NPC472619
0.8506	High Similarity	NPC473096
0.85	High Similarity	NPC197972
0.8497	Intermediate Similarity	NPC472621
0.8497	Intermediate Similarity	NPC13481
0.8497	Intermediate Similarity	NPC207575
0.8497	Intermediate Similarity	NPC475109
0.8497	Intermediate Similarity	NPC82330
0.8494	Intermediate Similarity	NPC476509
0.8494	Intermediate Similarity	NPC321387
0.8494	Intermediate Similarity	NPC327059
0.8494	Intermediate Similarity	NPC470908
0.8492	Intermediate Similarity	NPC313452
0.8492	Intermediate Similarity	NPC182693
0.8488	Intermediate Similarity	NPC473009
0.8485	Intermediate Similarity	NPC472345
0.8471	Intermediate Similarity	NPC470339
0.847	Intermediate Similarity	NPC470199
0.847	Intermediate Similarity	NPC314459
0.8462	Intermediate Similarity	NPC321372
0.8462	Intermediate Similarity	NPC295436
0.8462	Intermediate Similarity	NPC474609
0.8462	Intermediate Similarity	NPC10754
0.8462	Intermediate Similarity	NPC475797
0.8462	Intermediate Similarity	NPC477674
0.8462	Intermediate Similarity	NPC469936
0.8462	Intermediate Similarity	NPC78554
0.8462	Intermediate Similarity	NPC20530
0.8462	Intermediate Similarity	NPC474738
0.8462	Intermediate Similarity	NPC129053
0.8462	Intermediate Similarity	NPC109967
0.8462	Intermediate Similarity	NPC215917
0.8457	Intermediate Similarity	NPC102277
0.8457	Intermediate Similarity	NPC279209
0.8457	Intermediate Similarity	NPC315306
0.8457	Intermediate Similarity	NPC76047
0.8457	Intermediate Similarity	NPC313717
0.8453	Intermediate Similarity	NPC174486
0.8452	Intermediate Similarity	NPC311579
0.8452	Intermediate Similarity	NPC248793
0.8452	Intermediate Similarity	NPC180301
0.8452	Intermediate Similarity	NPC236756
0.8448	Intermediate Similarity	NPC76647
0.8448	Intermediate Similarity	NPC150131
0.8448	Intermediate Similarity	NPC473094
0.8448	Intermediate Similarity	NPC292233
0.8448	Intermediate Similarity	NPC260266
0.8441	Intermediate Similarity	NPC131405
0.8439	Intermediate Similarity	NPC472049
0.8439	Intermediate Similarity	NPC473010
0.8436	Intermediate Similarity	NPC315221
0.8436	Intermediate Similarity	NPC6709
0.8436	Intermediate Similarity	NPC475161
0.8436	Intermediate Similarity	NPC477860
0.843	Intermediate Similarity	NPC472402
0.843	Intermediate Similarity	NPC473012
0.8427	Intermediate Similarity	NPC207467
0.8424	Intermediate Similarity	NPC474108
0.8424	Intermediate Similarity	NPC177995
0.8421	Intermediate Similarity	NPC172687
0.8421	Intermediate Similarity	NPC306978
0.8421	Intermediate Similarity	NPC243701
0.8418	Intermediate Similarity	NPC474345
0.8412	Intermediate Similarity	NPC318527
0.8412	Intermediate Similarity	NPC282390
0.8412	Intermediate Similarity	NPC324358
0.8412	Intermediate Similarity	NPC281137
0.8412	Intermediate Similarity	NPC323627
0.8412	Intermediate Similarity	NPC322459
0.8409	Intermediate Similarity	NPC212038
0.8409	Intermediate Similarity	NPC271848
0.8409	Intermediate Similarity	NPC81332
0.8409	Intermediate Similarity	NPC262580
0.8409	Intermediate Similarity	NPC475669
0.8409	Intermediate Similarity	NPC289396
0.8402	Intermediate Similarity	NPC469934
0.8402	Intermediate Similarity	NPC477687
0.8402	Intermediate Similarity	NPC259710
0.8402	Intermediate Similarity	NPC279218
0.8402	Intermediate Similarity	NPC111341
0.8402	Intermediate Similarity	NPC476169
0.8402	Intermediate Similarity	NPC108937
0.8402	Intermediate Similarity	NPC207809
0.8402	Intermediate Similarity	NPC477671
0.8402	Intermediate Similarity	NPC304207
0.8402	Intermediate Similarity	NPC217706
0.8402	Intermediate Similarity	NPC304745
0.8402	Intermediate Similarity	NPC48579
0.84	Intermediate Similarity	NPC242395
0.84	Intermediate Similarity	NPC177480
0.84	Intermediate Similarity	NPC5319
0.84	Intermediate Similarity	NPC152477
0.8393	Intermediate Similarity	NPC256141
0.8391	Intermediate Similarity	NPC471823
0.8391	Intermediate Similarity	NPC120593
0.8391	Intermediate Similarity	NPC323137
0.8391	Intermediate Similarity	NPC251336

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 NPC476210 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	347
0.1-0.2	928
0.2-0.3	1989
0.3-0.4	2623
0.4-0.5	1948
0.5-0.6	911
0.6-0.7	266
0.7-0.8	135
0.8-0.85	3
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8521	High Similarity	NPD7075	Discontinued
0.8402	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.84	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8352	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.8343	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8284	Intermediate Similarity	NPD6801	Discontinued
0.8235	Intermediate Similarity	NPD7819	Suspended
0.8229	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8225	Intermediate Similarity	NPD7411	Suspended
0.8166	Intermediate Similarity	NPD4380	Phase 2
0.8132	Intermediate Similarity	NPD8434	Phase 2
0.8125	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8125	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8125	Intermediate Similarity	NPD6166	Phase 2
0.8111	Intermediate Similarity	NPD7808	Phase 3
0.8111	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8103	Intermediate Similarity	NPD5494	Approved
0.809	Intermediate Similarity	NPD5844	Phase 1
0.8084	Intermediate Similarity	NPD2532	Approved
0.8084	Intermediate Similarity	NPD2533	Approved
0.8084	Intermediate Similarity	NPD2534	Approved
0.8081	Intermediate Similarity	NPD5402	Approved
0.8079	Intermediate Similarity	NPD7473	Discontinued
0.8056	Intermediate Similarity	NPD7251	Discontinued
0.8033	Intermediate Similarity	NPD8150	Discontinued
0.8	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD6797	Phase 2
0.7989	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7978	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7977	Intermediate Similarity	NPD3817	Phase 2
0.7976	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7976	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7955	Intermediate Similarity	NPD6959	Discontinued
0.7933	Intermediate Similarity	NPD3818	Discontinued
0.7931	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7931	Intermediate Similarity	NPD3882	Suspended
0.7919	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.791	Intermediate Similarity	NPD6232	Discontinued
0.7889	Intermediate Similarity	NPD7054	Approved
0.7886	Intermediate Similarity	NPD3749	Approved
0.7882	Intermediate Similarity	NPD5403	Approved
0.7869	Intermediate Similarity	NPD8313	Approved
0.7869	Intermediate Similarity	NPD8312	Approved
0.7857	Intermediate Similarity	NPD6559	Discontinued
0.7849	Intermediate Similarity	NPD6599	Discontinued
0.7845	Intermediate Similarity	NPD7074	Phase 3
0.7845	Intermediate Similarity	NPD7472	Approved
0.7829	Intermediate Similarity	NPD7768	Phase 2
0.7824	Intermediate Similarity	NPD7435	Discontinued
0.7811	Intermediate Similarity	NPD6799	Approved
0.7765	Intermediate Similarity	NPD5401	Approved
0.7759	Intermediate Similarity	NPD1934	Approved
0.7753	Intermediate Similarity	NPD1247	Approved
0.7735	Intermediate Similarity	NPD3751	Discontinued
0.7714	Intermediate Similarity	NPD2801	Approved
0.7696	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7688	Intermediate Similarity	NPD3226	Approved
0.7679	Intermediate Similarity	NPD2800	Approved
0.7677	Intermediate Similarity	NPD7874	Approved
0.7677	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.766	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7641	Intermediate Similarity	NPD7698	Approved
0.7641	Intermediate Similarity	NPD7696	Phase 3
0.7641	Intermediate Similarity	NPD7697	Approved
0.764	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.764	Intermediate Similarity	NPD919	Approved
0.7619	Intermediate Similarity	NPD1549	Phase 2
0.7611	Intermediate Similarity	NPD5710	Approved
0.7611	Intermediate Similarity	NPD3787	Discontinued
0.7611	Intermediate Similarity	NPD5711	Approved
0.7602	Intermediate Similarity	NPD7870	Phase 2
0.7602	Intermediate Similarity	NPD7871	Phase 2
0.7577	Intermediate Similarity	NPD6778	Approved
0.7577	Intermediate Similarity	NPD6779	Approved
0.7577	Intermediate Similarity	NPD6781	Approved
0.7577	Intermediate Similarity	NPD6782	Approved
0.7577	Intermediate Similarity	NPD6777	Approved
0.7577	Intermediate Similarity	NPD6780	Approved
0.7577	Intermediate Similarity	NPD6776	Approved
0.7574	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.756	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.756	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7541	Intermediate Similarity	NPD7228	Approved
0.7538	Intermediate Similarity	NPD8151	Discontinued
0.7529	Intermediate Similarity	NPD3750	Approved
0.7515	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7514	Intermediate Similarity	NPD1512	Approved
0.7513	Intermediate Similarity	NPD8319	Approved
0.7513	Intermediate Similarity	NPD8320	Phase 1
0.75	Intermediate Similarity	NPD2796	Approved
0.7487	Intermediate Similarity	NPD7701	Phase 2
0.7474	Intermediate Similarity	NPD7700	Phase 2
0.7474	Intermediate Similarity	NPD7699	Phase 2
0.7471	Intermediate Similarity	NPD920	Approved
0.747	Intermediate Similarity	NPD5124	Phase 1
0.747	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7463	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7463	Intermediate Similarity	NPD7783	Phase 2
0.7463	Intermediate Similarity	NPD7801	Approved
0.7458	Intermediate Similarity	NPD37	Approved
0.744	Intermediate Similarity	NPD1510	Phase 2
0.7436	Intermediate Similarity	NPD8285	Discontinued
0.743	Intermediate Similarity	NPD4965	Approved
0.743	Intermediate Similarity	NPD4966	Approved
0.743	Intermediate Similarity	NPD4967	Phase 2
0.7416	Intermediate Similarity	NPD1465	Phase 2
0.7409	Intermediate Similarity	NPD6535	Approved
0.7409	Intermediate Similarity	NPD6534	Approved
0.7399	Intermediate Similarity	NPD1511	Approved
0.7377	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7356	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7353	Intermediate Similarity	NPD2346	Discontinued
0.7348	Intermediate Similarity	NPD6234	Discontinued
0.7326	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7326	Intermediate Similarity	NPD4628	Phase 3
0.7321	Intermediate Similarity	NPD6651	Approved
0.7308	Intermediate Similarity	NPD8366	Approved
0.7308	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.7294	Intermediate Similarity	NPD2935	Discontinued
0.7288	Intermediate Similarity	NPD7458	Discontinued
0.7288	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7287	Intermediate Similarity	NPD7685	Pre-registration
0.7283	Intermediate Similarity	NPD6190	Approved
0.7283	Intermediate Similarity	NPD3926	Phase 2
0.7268	Intermediate Similarity	NPD7199	Phase 2
0.7268	Intermediate Similarity	NPD8127	Discontinued
0.7267	Intermediate Similarity	NPD1243	Approved
0.7257	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7249	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7243	Intermediate Similarity	NPD2403	Approved
0.7241	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7236	Intermediate Similarity	NPD6823	Phase 2
0.7235	Intermediate Similarity	NPD2799	Discontinued
0.7235	Intermediate Similarity	NPD3748	Approved
0.7234	Intermediate Similarity	NPD5953	Discontinued
0.7228	Intermediate Similarity	NPD7229	Phase 3
0.7225	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD5760	Phase 2
0.7222	Intermediate Similarity	NPD5761	Phase 2
0.7222	Intermediate Similarity	NPD8455	Phase 2
0.7222	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD7286	Phase 2
0.7219	Intermediate Similarity	NPD1607	Approved
0.7202	Intermediate Similarity	NPD1240	Approved
0.7196	Intermediate Similarity	NPD7240	Approved
0.7193	Intermediate Similarity	NPD6100	Approved
0.7193	Intermediate Similarity	NPD6099	Approved
0.7193	Intermediate Similarity	NPD1551	Phase 2
0.7186	Intermediate Similarity	NPD2313	Discontinued
0.7175	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD8491	Approved
0.7166	Intermediate Similarity	NPD7799	Discontinued
0.7166	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7136	Intermediate Similarity	NPD8469	Approved
0.7113	Intermediate Similarity	NPD4287	Approved
0.7105	Intermediate Similarity	NPD6765	Approved
0.7105	Intermediate Similarity	NPD6764	Approved
0.7102	Intermediate Similarity	NPD7390	Discontinued
0.7094	Intermediate Similarity	NPD7584	Approved
0.7083	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD8407	Phase 2
0.7059	Intermediate Similarity	NPD6355	Discontinued
0.7056	Intermediate Similarity	NPD4360	Phase 2
0.7056	Intermediate Similarity	NPD4363	Phase 3
0.7052	Intermediate Similarity	NPD1471	Phase 3
0.7045	Intermediate Similarity	NPD7236	Approved
0.7035	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7035	Intermediate Similarity	NPD7033	Discontinued
0.7033	Intermediate Similarity	NPD8404	Phase 2
0.7022	Intermediate Similarity	NPD6273	Approved
0.7017	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7016	Intermediate Similarity	NPD8368	Discontinued
0.6982	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6982	Remote Similarity	NPD3268	Approved
0.6982	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD7907	Approved
0.6977	Remote Similarity	NPD7097	Phase 1
0.6961	Remote Similarity	NPD7211	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD6784	Approved
0.6959	Remote Similarity	NPD8067	Phase 3
0.6959	Remote Similarity	NPD6785	Approved
0.6954	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD2344	Approved
0.6944	Remote Similarity	NPD7239	Suspended
0.6944	Remote Similarity	NPD1653	Approved
0.6939	Remote Similarity	NPD8360	Approved
0.6939	Remote Similarity	NPD8361	Approved
0.6939	Remote Similarity	NPD8435	Approved
0.6932	Remote Similarity	NPD7982	Clinical (unspecified phase)
0.6932	Remote Similarity	NPD7003	Approved
0.6919	Remote Similarity	NPD6212	Phase 3
0.6919	Remote Similarity	NPD6214	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD6213	Phase 3
0.6901	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6901	Remote Similarity	NPD4060	Phase 1
0.69	Remote Similarity	NPD8485	Approved
0.6897	Remote Similarity	NPD5404	Approved
0.6897	Remote Similarity	NPD5406	Approved
0.6897	Remote Similarity	NPD5405	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