NPASS Compound

Structure

CID269466 OpenBabel06191716072D 43 47 0 0 1 0 0 0 0 0999 V2000 0.3292 4.1609 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1968 5.7783 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8605 6.1314 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8514 -2.4927 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2533 1.4744 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0003 1.0186 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5545 2.4916 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6046 3.8572 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2682 4.2104 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4721 3.2499 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7022 -0.9834 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8508 -1.4746 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2553 0.4902 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2555 1.4726 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8517 1.4735 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7013 0.0005 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7031 1.9647 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8505 0.4917 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1306 5.4746 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8511 -1.4741 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.2536 0.4919 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.3345 4.5141 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7025 -0.0005 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4059 2.9462 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0003 -0.9829 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5539 0.4907 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.4056 1.9643 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8514 0.4912 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7016 -0.9824 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.1046 0.0010 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.1048 -0.9815 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.2542 -1.4729 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.1358 3.6030 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4032 -0.9819 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5542 1.4730 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.9552 0.4924 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.9558 -1.4724 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2544 -2.4553 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.9319 4.5635 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4029 0.0005 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5526 -1.4734 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.0695 3.2993 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0 1 8 1 0 0 0 0 2 19 1 0 0 0 0 3 19 1 0 0 0 0 8 22 2 0 0 0 0 9 10 1 0 0 0 0 9 22 1 0 0 0 0 11 12 1 0 0 0 0 11 23 2 0 0 0 0 12 25 1 0 0 0 0 13 14 1 0 0 0 0 13 26 1 0 0 0 0 14 27 1 0 0 0 0 15 17 1 0 0 0 0 15 28 1 0 0 0 0 16 18 1 0 0 0 0 16 29 1 0 0 0 0 17 36 1 0 0 0 0 18 35 1 0 0 0 0 19 22 1 0 0 0 0 20 4 1 1 0 0 0 20 25 1 0 0 0 0 20 29 1 0 0 0 0 21 5 1 1 0 0 0 21 30 1 0 0 0 0 21 41 1 0 0 0 0 23 26 1 0 0 0 0 23 28 1 0 0 0 0 24 10 1 6 0 0 0 24 27 1 0 0 0 0 24 33 1 0 0 0 0 25 35 1 6 0 0 0 26 36 1 6 0 0 0 27 36 1 6 0 0 0 28 35 1 6 0 0 0 29 42 1 6 0 0 0 30 31 1 0 0 0 0 30 37 1 6 0 0 0 31 32 1 0 0 0 0 31 38 1 1 0 0 0 32 34 1 0 0 0 0 32 39 1 6 0 0 0 33 40 2 0 0 0 0 33 43 1 0 0 0 0 34 41 1 0 0 0 0 34 42 1 6 0 0 0 35 6 1 6 0 0 0 36 7 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	618.4
Volume:	651.771
LogP:	5.935
LogD:	5.304
LogS:	-4.994
# Rotatable Bonds:	8
TPSA:	96.22
# H-Bond Aceptor:	6
# H-Bond Donor:	3
# Rings:	5
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.184
Synthetic Accessibility Score:	5.587
Fsp3:	0.861
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:	-4.831
MDCK Permeability:	8.201759555959143e-06
Pgp-inhibitor:	0.907
Pgp-substrate:	0.295
Human Intestinal Absorption (HIA):	0.366
20% Bioavailability (F20%):	0.948
30% Bioavailability (F30%):	0.792

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.003
Plasma Protein Binding (PPB):	97.69998931884766%
Volume Distribution (VD):	1.496
Pgp-substrate:	1.6939716339111328%

ADMET: Metabolism

CYP1A2-inhibitor:	0.021
CYP1A2-substrate:	0.358
CYP2C19-inhibitor:	0.03
CYP2C19-substrate:	0.883
CYP2C9-inhibitor:	0.139
CYP2C9-substrate:	0.095
CYP2D6-inhibitor:	0.016
CYP2D6-substrate:	0.494
CYP3A4-inhibitor:	0.653
CYP3A4-substrate:	0.475

ADMET: Excretion

Clearance (CL):	6.311
Half-life (T1/2):	0.331

ADMET: Toxicity

hERG Blockers:	0.053
Human Hepatotoxicity (H-HT):	0.173
Drug-inuced Liver Injury (DILI):	0.34
AMES Toxicity:	0.018
Rat Oral Acute Toxicity:	0.197
Maximum Recommended Daily Dose:	0.019
Skin Sensitization:	0.709
Carcinogencity:	0.028
Eye Corrosion:	0.003
Eye Irritation:	0.015
Respiratory Toxicity:	0.983

Download Data

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

Natural Product: NPC269466

Natural Product ID:	NPC269466
*Common Name:**	Fruticoside G
IUPAC Name:	(Z,2R)-5-propan-2-yl-2-[(3S,4S,5S,9R,10S,13R,14R,17R)-4,10,13-trimethyl-3-[(2R,3S,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy-2,3,4,5,6,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]hept-5-enethioic S-acid
Synonyms:	Fruticoside G
Standard InCHIKey:	AUQOSBIEPMUBCQ-TVZJVHHSSA-N
Standard InCHI:	InChI=1S/C36H58O6S/c1-8-22(19(2)3)9-10-24(33(40)43)27-14-13-26-23-11-12-25-20(4)29(42-34-32(39)31(38)30(37)21(5)41-34)16-18-35(25,6)28(23)15-17-36(26,27)7/h8,11,19-21,24-32,34,37-39H,9-10,12-18H2,1-7H3,(H,40,43)/b22-8-/t20-,21-,24+,25-,26-,27+,28-,29-,30-,31+,32-,34-,35-,36-/m0/s1
SMILES:	C/C=C(/CC[C@H]([C@H]1CC[C@H]2C3=CC[C@H]4[C@H](C)[C@H](CC[C@]4(C)[C@H]3CC[C@]12C)O[C@H]1[C@H]([C@@H]([C@H]([C@H](C)O1)O)O)O)C(=O)S)C(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1782596
PubChem CID:	54587064
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0002031] Stigmastanes and derivatives

*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
NPO26000	Breynia fruticosa	Species	Phyllanthaceae	Eukaryota	n.a.	root	n.a.	PMID[21428418]
NPO26000	Breynia fruticosa	Species	Phyllanthaceae	Eukaryota	roots	Xishuangbanna of Yunnan Province, China	n.a.	PMID[21428418]
NPO26000	Breynia fruticosa	Species	Phyllanthaceae	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	5

Activity Type	# Activity
Cell Line	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT116	Cell Line	HL-60	Homo sapiens	IC50	>	40000.0	nM	PMID[476706]
NPT659	Cell Line	SMMC-7721	Homo sapiens	IC50	>	40000.0	nM	PMID[476706]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	40000.0	nM	PMID[476706]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	>	40000.0	nM	PMID[476706]
NPT660	Cell Line	SW480	Homo sapiens	IC50	>	40000.0	nM	PMID[476706]

☑ 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 NPC269466 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	216
0.1-0.2	1489
0.2-0.3	5157
0.3-0.4	12065
0.4-0.5	9903
0.5-0.6	5713
0.6-0.7	4642
0.7-0.8	2863
0.8-0.85	579
0.85-0.9	53
0.9-0.95	15
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9623	High Similarity	NPC244127
0.9245	High Similarity	NPC263827
0.9245	High Similarity	NPC285410
0.9245	High Similarity	NPC250481
0.9151	High Similarity	NPC52241
0.9151	High Similarity	NPC154856
0.9151	High Similarity	NPC129340
0.9151	High Similarity	NPC475317
0.9143	High Similarity	NPC295389
0.9074	High Similarity	NPC260665
0.9057	High Similarity	NPC265655
0.8981	High Similarity	NPC210420
0.8981	High Similarity	NPC474265
0.8981	High Similarity	NPC130427
0.8972	High Similarity	NPC101450
0.8962	High Similarity	NPC195708
0.8899	High Similarity	NPC251309
0.8889	High Similarity	NPC292196
0.8879	High Similarity	NPC246205
0.8818	High Similarity	NPC74727
0.8818	High Similarity	NPC473882
0.8818	High Similarity	NPC474557
0.8807	High Similarity	NPC233003
0.8774	High Similarity	NPC63023
0.8774	High Similarity	NPC210178
0.8774	High Similarity	NPC95243
0.8774	High Similarity	NPC162033
0.8739	High Similarity	NPC279638
0.8738	High Similarity	NPC280825
0.8738	High Similarity	NPC234287
0.8704	High Similarity	NPC57362
0.8704	High Similarity	NPC477069
0.8704	High Similarity	NPC167383
0.8704	High Similarity	NPC204407
0.8704	High Similarity	NPC237503
0.8704	High Similarity	NPC137917
0.8704	High Similarity	NPC306746
0.8704	High Similarity	NPC477070
0.8692	High Similarity	NPC283849
0.8684	High Similarity	NPC476672
0.8684	High Similarity	NPC476675
0.8679	High Similarity	NPC223741
0.8679	High Similarity	NPC121566
0.8679	High Similarity	NPC100955
0.8654	High Similarity	NPC473200
0.8654	High Similarity	NPC7341
0.8649	High Similarity	NPC220293
0.8649	High Similarity	NPC477580
0.8649	High Similarity	NPC116024
0.8641	High Similarity	NPC243728
0.8641	High Similarity	NPC473890
0.8624	High Similarity	NPC476886
0.8624	High Similarity	NPC108709
0.8624	High Similarity	NPC475296
0.8624	High Similarity	NPC476881
0.8624	High Similarity	NPC476887
0.8624	High Similarity	NPC110139
0.8624	High Similarity	NPC56713
0.8624	High Similarity	NPC136877
0.8624	High Similarity	NPC7870
0.8624	High Similarity	NPC274507
0.8624	High Similarity	NPC476880
0.8624	High Similarity	NPC476884
0.8624	High Similarity	NPC59804
0.8624	High Similarity	NPC476882
0.8624	High Similarity	NPC78046
0.8624	High Similarity	NPC174679
0.8624	High Similarity	NPC474589
0.8624	High Similarity	NPC102914
0.8624	High Similarity	NPC476885
0.8624	High Similarity	NPC270667
0.8624	High Similarity	NPC164194
0.8624	High Similarity	NPC75747
0.8624	High Similarity	NPC90856
0.8624	High Similarity	NPC279554
0.8624	High Similarity	NPC220984
0.8624	High Similarity	NPC29069
0.8624	High Similarity	NPC476883
0.8624	High Similarity	NPC68419
0.8624	High Similarity	NPC199457
0.8624	High Similarity	NPC269095
0.8624	High Similarity	NPC127056
0.8611	High Similarity	NPC28198
0.8611	High Similarity	NPC284807
0.8611	High Similarity	NPC88744
0.8611	High Similarity	NPC177246
0.8611	High Similarity	NPC476123
0.8598	High Similarity	NPC473199
0.8596	High Similarity	NPC471406
0.8584	High Similarity	NPC45475
0.8584	High Similarity	NPC239293
0.8571	High Similarity	NPC47566
0.8571	High Similarity	NPC4831
0.8571	High Similarity	NPC309425
0.8571	High Similarity	NPC472023
0.8571	High Similarity	NPC129372
0.8571	High Similarity	NPC160734
0.8571	High Similarity	NPC88000
0.8559	High Similarity	NPC178981
0.8559	High Similarity	NPC477944
0.8558	High Similarity	NPC158088
0.8545	High Similarity	NPC235841
0.8545	High Similarity	NPC164419
0.8545	High Similarity	NPC191763
0.8545	High Similarity	NPC477073
0.8545	High Similarity	NPC211798
0.8545	High Similarity	NPC473481
0.8545	High Similarity	NPC31839
0.8545	High Similarity	NPC297208
0.8545	High Similarity	NPC179434
0.8545	High Similarity	NPC108748
0.8545	High Similarity	NPC30397
0.8532	High Similarity	NPC8431
0.8532	High Similarity	NPC240125
0.8532	High Similarity	NPC473844
0.8532	High Similarity	NPC51947
0.8532	High Similarity	NPC91583
0.8532	High Similarity	NPC127853
0.8532	High Similarity	NPC118225
0.8519	High Similarity	NPC473538
0.8519	High Similarity	NPC293512
0.8519	High Similarity	NPC234160
0.8509	High Similarity	NPC477071
0.8505	High Similarity	NPC85593
0.8505	High Similarity	NPC75608
0.8505	High Similarity	NPC31430
0.8505	High Similarity	NPC470885
0.8505	High Similarity	NPC221562
0.8505	High Similarity	NPC187400
0.8491	Intermediate Similarity	NPC154452
0.8491	Intermediate Similarity	NPC159036
0.8491	Intermediate Similarity	NPC312553
0.8491	Intermediate Similarity	NPC94919
0.8491	Intermediate Similarity	NPC136816
0.8491	Intermediate Similarity	NPC288694
0.8482	Intermediate Similarity	NPC165439
0.8476	Intermediate Similarity	NPC282669
0.8468	Intermediate Similarity	NPC471383
0.8468	Intermediate Similarity	NPC80843
0.8468	Intermediate Similarity	NPC116794
0.8468	Intermediate Similarity	NPC139044
0.8468	Intermediate Similarity	NPC48249
0.8468	Intermediate Similarity	NPC256798
0.8468	Intermediate Similarity	NPC79718
0.8468	Intermediate Similarity	NPC257468
0.8468	Intermediate Similarity	NPC104400
0.8468	Intermediate Similarity	NPC109079
0.8468	Intermediate Similarity	NPC10320
0.8468	Intermediate Similarity	NPC477253
0.8468	Intermediate Similarity	NPC469946
0.8468	Intermediate Similarity	NPC324875
0.8468	Intermediate Similarity	NPC473373
0.8468	Intermediate Similarity	NPC104071
0.8468	Intermediate Similarity	NPC46388
0.8468	Intermediate Similarity	NPC276093
0.8468	Intermediate Similarity	NPC475504
0.8468	Intermediate Similarity	NPC139894
0.8468	Intermediate Similarity	NPC471967
0.8468	Intermediate Similarity	NPC37739
0.8468	Intermediate Similarity	NPC102439
0.8468	Intermediate Similarity	NPC475516
0.8468	Intermediate Similarity	NPC473383
0.8468	Intermediate Similarity	NPC128925
0.8468	Intermediate Similarity	NPC292677
0.8468	Intermediate Similarity	NPC101744
0.8468	Intermediate Similarity	NPC1046
0.8462	Intermediate Similarity	NPC476674
0.8455	Intermediate Similarity	NPC27551
0.8455	Intermediate Similarity	NPC242611
0.8455	Intermediate Similarity	NPC114961
0.8448	Intermediate Similarity	NPC28532
0.844	Intermediate Similarity	NPC472988
0.844	Intermediate Similarity	NPC258323
0.844	Intermediate Similarity	NPC38217
0.8435	Intermediate Similarity	NPC472257
0.8435	Intermediate Similarity	NPC129393
0.8435	Intermediate Similarity	NPC470312
0.8426	Intermediate Similarity	NPC475611
0.8426	Intermediate Similarity	NPC242748
0.8421	Intermediate Similarity	NPC86020
0.8421	Intermediate Similarity	NPC475632
0.8411	Intermediate Similarity	NPC245280
0.8411	Intermediate Similarity	NPC16520
0.8411	Intermediate Similarity	NPC473020
0.8411	Intermediate Similarity	NPC213190
0.8411	Intermediate Similarity	NPC211879
0.8411	Intermediate Similarity	NPC31907
0.8411	Intermediate Similarity	NPC8039
0.8411	Intermediate Similarity	NPC472252
0.8411	Intermediate Similarity	NPC473198
0.8411	Intermediate Similarity	NPC286969
0.8411	Intermediate Similarity	NPC189852
0.8411	Intermediate Similarity	NPC120123
0.8411	Intermediate Similarity	NPC157659
0.8411	Intermediate Similarity	NPC16573
0.8411	Intermediate Similarity	NPC155010
0.8411	Intermediate Similarity	NPC131479
0.8411	Intermediate Similarity	NPC114874
0.8396	Intermediate Similarity	NPC267510
0.8396	Intermediate Similarity	NPC470434

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 NPC269466 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	182
0.1-0.2	1672
0.2-0.3	4121
0.3-0.4	2141
0.4-0.5	531
0.5-0.6	253
0.6-0.7	179
0.7-0.8	69
0.8-0.85	1
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8692	High Similarity	NPD6412	Phase 2
0.8198	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7934	Intermediate Similarity	NPD7507	Approved
0.7917	Intermediate Similarity	NPD6067	Discontinued
0.7913	Intermediate Similarity	NPD8133	Approved
0.7833	Intermediate Similarity	NPD6370	Approved
0.7805	Intermediate Similarity	NPD7736	Approved
0.7788	Intermediate Similarity	NPD6686	Approved
0.7769	Intermediate Similarity	NPD8328	Phase 3
0.7742	Intermediate Similarity	NPD7319	Approved
0.7724	Intermediate Similarity	NPD8293	Discontinued
0.7712	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7667	Intermediate Similarity	NPD6054	Approved
0.7667	Intermediate Similarity	NPD8294	Approved
0.7667	Intermediate Similarity	NPD8377	Approved
0.7667	Intermediate Similarity	NPD6059	Approved
0.7647	Intermediate Similarity	NPD7328	Approved
0.7647	Intermediate Similarity	NPD7327	Approved
0.7603	Intermediate Similarity	NPD8033	Approved
0.7603	Intermediate Similarity	NPD8378	Approved
0.7603	Intermediate Similarity	NPD8380	Approved
0.7603	Intermediate Similarity	NPD8335	Approved
0.7603	Intermediate Similarity	NPD8379	Approved
0.7603	Intermediate Similarity	NPD8296	Approved
0.7583	Intermediate Similarity	NPD7516	Approved
0.7459	Intermediate Similarity	NPD7503	Approved
0.7459	Intermediate Similarity	NPD6016	Approved
0.7459	Intermediate Similarity	NPD6015	Approved
0.7436	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD7492	Approved
0.7417	Intermediate Similarity	NPD6009	Approved
0.7407	Intermediate Similarity	NPD6399	Phase 3
0.7398	Intermediate Similarity	NPD5988	Approved
0.7373	Intermediate Similarity	NPD6882	Approved
0.7373	Intermediate Similarity	NPD8297	Approved
0.7368	Intermediate Similarity	NPD8170	Clinical (unspecified phase)
0.736	Intermediate Similarity	NPD6616	Approved
0.7315	Intermediate Similarity	NPD8034	Phase 2
0.7315	Intermediate Similarity	NPD8035	Phase 2
0.7311	Intermediate Similarity	NPD4632	Approved
0.7308	Intermediate Similarity	NPD4786	Approved
0.7304	Intermediate Similarity	NPD7128	Approved
0.7304	Intermediate Similarity	NPD5739	Approved
0.7304	Intermediate Similarity	NPD6675	Approved
0.7304	Intermediate Similarity	NPD6402	Approved
0.7302	Intermediate Similarity	NPD7078	Approved
0.729	Intermediate Similarity	NPD5328	Approved
0.7281	Intermediate Similarity	NPD4754	Approved
0.7236	Intermediate Similarity	NPD6319	Approved
0.7232	Intermediate Similarity	NPD7638	Approved
0.7182	Intermediate Similarity	NPD7748	Approved
0.7179	Intermediate Similarity	NPD7320	Approved
0.7179	Intermediate Similarity	NPD6881	Approved
0.7179	Intermediate Similarity	NPD6899	Approved
0.717	Intermediate Similarity	NPD3618	Phase 1
0.7168	Intermediate Similarity	NPD7640	Approved
0.7168	Intermediate Similarity	NPD7639	Approved
0.7156	Intermediate Similarity	NPD6079	Approved
0.7143	Intermediate Similarity	NPD4755	Approved
0.7143	Intermediate Similarity	NPD7902	Approved
0.7143	Intermediate Similarity	NPD8130	Phase 1
0.7131	Intermediate Similarity	NPD7115	Discovery
0.7119	Intermediate Similarity	NPD6373	Approved
0.7119	Intermediate Similarity	NPD6372	Approved
0.7115	Intermediate Similarity	NPD3667	Approved
0.7109	Intermediate Similarity	NPD6033	Approved
0.7094	Intermediate Similarity	NPD5697	Approved
0.7094	Intermediate Similarity	NPD5701	Approved
0.7091	Intermediate Similarity	NPD4202	Approved
0.7075	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD7290	Approved
0.7059	Intermediate Similarity	NPD7102	Approved
0.7059	Intermediate Similarity	NPD4634	Approved
0.7059	Intermediate Similarity	NPD6883	Approved
0.704	Intermediate Similarity	NPD8516	Approved
0.704	Intermediate Similarity	NPD8513	Phase 3
0.704	Intermediate Similarity	NPD8515	Approved
0.704	Intermediate Similarity	NPD8517	Approved
0.7018	Intermediate Similarity	NPD5286	Approved
0.7018	Intermediate Similarity	NPD5285	Approved
0.7018	Intermediate Similarity	NPD4700	Approved
0.7018	Intermediate Similarity	NPD4696	Approved
0.7	Intermediate Similarity	NPD6869	Approved
0.7	Intermediate Similarity	NPD7515	Phase 2
0.7	Intermediate Similarity	NPD6649	Approved
0.7	Intermediate Similarity	NPD6617	Approved
0.7	Intermediate Similarity	NPD6650	Approved
0.7	Intermediate Similarity	NPD6847	Approved
0.6991	Remote Similarity	NPD6083	Phase 2
0.6991	Remote Similarity	NPD6084	Phase 2
0.6975	Remote Similarity	NPD6014	Approved
0.6975	Remote Similarity	NPD6012	Approved
0.6975	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD6013	Approved
0.6937	Remote Similarity	NPD8171	Discontinued
0.6929	Remote Similarity	NPD7604	Phase 2
0.6923	Remote Similarity	NPD7525	Registered
0.6905	Remote Similarity	NPD5983	Phase 2
0.6903	Remote Similarity	NPD5221	Approved
0.6903	Remote Similarity	NPD5222	Approved
0.6903	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6903	Remote Similarity	NPD4697	Phase 3
0.6897	Remote Similarity	NPD5211	Phase 2
0.6897	Remote Similarity	NPD4633	Approved
0.6897	Remote Similarity	NPD5226	Approved
0.6897	Remote Similarity	NPD5225	Approved
0.6897	Remote Similarity	NPD5224	Approved
0.6891	Remote Similarity	NPD6011	Approved
0.6875	Remote Similarity	NPD7900	Approved
0.6875	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6864	Remote Similarity	NPD6008	Approved
0.6855	Remote Similarity	NPD6317	Approved
0.6842	Remote Similarity	NPD5173	Approved
0.6838	Remote Similarity	NPD5174	Approved
0.6838	Remote Similarity	NPD5175	Approved
0.6822	Remote Similarity	NPD3665	Phase 1
0.6822	Remote Similarity	NPD6336	Discontinued
0.6822	Remote Similarity	NPD3133	Approved
0.6822	Remote Similarity	NPD3666	Approved
0.6822	Remote Similarity	NPD3668	Phase 3
0.6818	Remote Similarity	NPD4753	Phase 2
0.681	Remote Similarity	NPD5223	Approved
0.678	Remote Similarity	NPD5141	Approved
0.6777	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6777	Remote Similarity	NPD5135	Approved
0.675	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6727	Remote Similarity	NPD6672	Approved
0.6727	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6727	Remote Similarity	NPD5737	Approved
0.6723	Remote Similarity	NPD4767	Approved
0.6723	Remote Similarity	NPD4768	Approved
0.6697	Remote Similarity	NPD7334	Approved
0.6697	Remote Similarity	NPD6684	Approved
0.6697	Remote Similarity	NPD7521	Approved
0.6697	Remote Similarity	NPD6409	Approved
0.6697	Remote Similarity	NPD7146	Approved
0.6697	Remote Similarity	NPD5330	Approved
0.6667	Remote Similarity	NPD5695	Phase 3
0.6667	Remote Similarity	NPD7645	Phase 2
0.6642	Remote Similarity	NPD8449	Approved
0.6641	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.664	Remote Similarity	NPD6940	Discontinued
0.664	Remote Similarity	NPD6274	Approved
0.6639	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6638	Remote Similarity	NPD5696	Approved
0.6636	Remote Similarity	NPD7524	Approved
0.6617	Remote Similarity	NPD5956	Approved
0.6614	Remote Similarity	NPD7100	Approved
0.6614	Remote Similarity	NPD7101	Approved
0.6612	Remote Similarity	NPD4730	Approved
0.6612	Remote Similarity	NPD4729	Approved
0.6612	Remote Similarity	NPD5128	Approved
0.661	Remote Similarity	NPD7632	Discontinued
0.6602	Remote Similarity	NPD7339	Approved
0.6602	Remote Similarity	NPD6942	Approved
0.6593	Remote Similarity	NPD8450	Suspended
0.6585	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6577	Remote Similarity	NPD6903	Approved
0.6571	Remote Similarity	NPD6118	Approved
0.6571	Remote Similarity	NPD6115	Approved
0.6571	Remote Similarity	NPD6114	Approved
0.6571	Remote Similarity	NPD6697	Approved
0.6549	Remote Similarity	NPD6411	Approved
0.6545	Remote Similarity	NPD5279	Phase 3
0.6535	Remote Similarity	NPD6335	Approved
0.6522	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD4629	Approved
0.6522	Remote Similarity	NPD5210	Approved
0.6514	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6512	Remote Similarity	NPD6908	Approved
0.6512	Remote Similarity	NPD6909	Approved
0.6508	Remote Similarity	NPD6868	Approved
0.6504	Remote Similarity	NPD5249	Phase 3
0.6504	Remote Similarity	NPD5248	Approved
0.6504	Remote Similarity	NPD5250	Approved
0.6504	Remote Similarity	NPD5251	Approved
0.6504	Remote Similarity	NPD5247	Approved
0.6503	Remote Similarity	NPD7625	Phase 1
0.6496	Remote Similarity	NPD4225	Approved
0.6481	Remote Similarity	NPD4223	Phase 3
0.6481	Remote Similarity	NPD4221	Approved
0.6476	Remote Similarity	NPD6116	Phase 1
0.6455	Remote Similarity	NPD5329	Approved
0.6452	Remote Similarity	NPD5217	Approved
0.6452	Remote Similarity	NPD5216	Approved
0.6452	Remote Similarity	NPD5215	Approved
0.6449	Remote Similarity	NPD6928	Phase 2
0.6422	Remote Similarity	NPD6695	Phase 3
0.6406	Remote Similarity	NPD6314	Approved
0.6406	Remote Similarity	NPD6313	Approved
0.6404	Remote Similarity	NPD7637	Suspended
0.64	Remote Similarity	NPD6053	Discontinued
0.6396	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6396	Remote Similarity	NPD6098	Approved
0.6393	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6391	Remote Similarity	NPD8074	Phase 3
0.6381	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6381	Remote Similarity	NPD6117	Approved
0.6372	Remote Similarity	NPD6080	Approved
0.6372	Remote Similarity	NPD6904	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