NPASS Compound

Structure

CID189520 OpenBabel06191715572D 33 36 0 0 1 0 0 0 0 0999 V2000 1.8857 -6.7155 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5383 -7.0662 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2908 -4.8073 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8445 1.5002 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2276 -3.4508 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6905 -1.9876 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9433 -5.1581 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1458 -4.2040 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3811 0.0010 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5354 0.4889 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9170 -1.4628 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9173 -2.4386 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5362 -2.4395 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3819 -2.9275 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8454 -1.4643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8133 -6.4138 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0158 -5.4597 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8448 0.4884 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.3814 -0.9754 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0733 -3.9023 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6899 0.0005 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.2271 -1.4633 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.0730 -2.9270 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5359 -1.4638 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0003 -0.9763 0.0000 C 0 0 2 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 5.7983 -4.5547 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2273 -2.4390 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6902 -0.9759 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8657 -1.4765 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8662 0.4996 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.5958 -5.5088 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.7259 -4.2531 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 16 1 0 0 0 0 2 16 1 0 0 0 0 3 17 2 0 0 0 0 7 8 1 0 0 0 0 7 17 1 0 0 0 0 9 10 1 0 0 0 0 9 19 2 0 0 0 0 10 21 1 0 0 0 0 11 12 1 0 0 0 0 11 22 1 0 0 0 0 12 23 1 0 0 0 0 13 14 1 0 0 0 0 13 24 1 0 0 0 0 14 28 1 0 0 0 0 15 25 1 0 0 0 0 15 29 1 0 0 0 0 16 17 1 0 0 0 0 18 4 1 1 0 0 0 18 21 1 0 0 0 0 18 26 1 0 0 0 0 19 22 1 0 0 0 0 19 24 1 0 0 0 0 20 8 1 6 0 0 0 20 23 1 0 0 0 0 20 27 1 0 0 0 0 21 29 1 6 0 0 0 22 28 1 6 0 0 0 23 28 1 6 0 0 0 24 29 1 6 0 0 0 25 26 1 0 0 0 0 25 30 1 1 0 0 0 26 31 1 6 0 0 0 27 32 2 0 0 0 0 27 33 1 0 0 0 0 28 5 1 6 0 0 0 29 6 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	458.34
Volume:	503.166
LogP:	5.458
LogD:	4.979
LogS:	-4.861
# Rotatable Bonds:	6
TPSA:	77.76
# H-Bond Aceptor:	4
# H-Bond Donor:	3
# Rings:	4
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.437
Synthetic Accessibility Score:	5.027
Fsp3:	0.828
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.046
MDCK Permeability:	1.6782563761807978e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.007
Human Intestinal Absorption (HIA):	0.008
20% Bioavailability (F20%):	0.963
30% Bioavailability (F30%):	0.819

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.018
Plasma Protein Binding (PPB):	96.46177673339844%
Volume Distribution (VD):	0.611
Pgp-substrate:	2.8304247856140137%

ADMET: Metabolism

CYP1A2-inhibitor:	0.024
CYP1A2-substrate:	0.244
CYP2C19-inhibitor:	0.009
CYP2C19-substrate:	0.802
CYP2C9-inhibitor:	0.065
CYP2C9-substrate:	0.921
CYP2D6-inhibitor:	0.003
CYP2D6-substrate:	0.433
CYP3A4-inhibitor:	0.163
CYP3A4-substrate:	0.095

ADMET: Excretion

Clearance (CL):	1.745
Half-life (T1/2):	0.376

ADMET: Toxicity

hERG Blockers:	0.035
Human Hepatotoxicity (H-HT):	0.35
Drug-inuced Liver Injury (DILI):	0.309
AMES Toxicity:	0.005
Rat Oral Acute Toxicity:	0.305
Maximum Recommended Daily Dose:	0.085
Skin Sensitization:	0.09
Carcinogencity:	0.043
Eye Corrosion:	0.005
Eye Irritation:	0.042
Respiratory Toxicity:	0.957

Download Data

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

Natural Product: NPC189520

Natural Product ID:	NPC189520
*Common Name:**	Fruticoside B
IUPAC Name:	(2R)-2-[(2R,3R,4S,5S,9R,10S,13R,14R,17R)-2,3-dihydroxy-4,10,13-trimethyl-2,3,4,5,6,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]-6-methyl-5-methylideneheptanoic acid
Synonyms:	Fruticoside B
Standard InCHIKey:	AYCQAFSTPBCSLH-GDMQXADVSA-N
Standard InCHI:	InChI=1S/C29H46O4/c1-16(2)17(3)7-8-20(27(32)33)23-12-11-22-19-9-10-21-18(4)26(31)25(30)15-29(21,6)24(19)13-14-28(22,23)5/h9,16,18,20-26,30-31H,3,7-8,10-15H2,1-2,4-6H3,(H,32,33)/t18-,20+,21-,22-,23+,24-,25+,26+,28-,29-/m0/s1
SMILES:	CC(C)C(=C)CC[C@H]([C@H]1CC[C@H]2C3=CC[C@H]4[C@H](C)[C@H]([C@@H](C[C@]4(C)[C@H]3CC[C@]12C)O)O)C(=O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1782591
PubChem CID:	53355689
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001445] Bile acids, alcohols and derivatives [CHEMONTID:0002194] Hydroxy bile acids, alcohols and derivatives [CHEMONTID:0000516] Dihydroxy bile acids, alcohols 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[501778]
NPT659	Cell Line	SMMC-7721	Homo sapiens	IC50	>	40000.0	nM	PMID[501778]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	40000.0	nM	PMID[501778]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	>	40000.0	nM	PMID[501778]
NPT660	Cell Line	SW480	Homo sapiens	IC50	>	40000.0	nM	PMID[501778]

☑ 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 NPC189520 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	171
0.1-0.2	1048
0.2-0.3	4503
0.3-0.4	13808
0.4-0.5	8474
0.5-0.6	5652
0.6-0.7	5127
0.7-0.8	3255
0.8-0.85	529
0.85-0.9	118
0.9-0.95	6
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
0.9535	High Similarity	NPC474704
0.9535	High Similarity	NPC475921
0.9529	High Similarity	NPC474684
0.9529	High Similarity	NPC142361
0.9302	High Similarity	NPC187376
0.9302	High Similarity	NPC233836
0.9302	High Similarity	NPC159046
0.9213	High Similarity	NPC470376
0.9213	High Similarity	NPC470375
0.9205	High Similarity	NPC471896
0.9195	High Similarity	NPC242864
0.9186	High Similarity	NPC28252
0.9186	High Similarity	NPC155011
0.9186	High Similarity	NPC55309
0.9101	High Similarity	NPC212301
0.9101	High Similarity	NPC472149
0.9101	High Similarity	NPC25299
0.9101	High Similarity	NPC52021
0.9101	High Similarity	NPC84319
0.9101	High Similarity	NPC86266
0.9101	High Similarity	NPC306541
0.9101	High Similarity	NPC235884
0.9101	High Similarity	NPC71074
0.9101	High Similarity	NPC300351
0.9101	High Similarity	NPC110657
0.9091	High Similarity	NPC32830
0.9091	High Similarity	NPC77168
0.9091	High Similarity	NPC84271
0.9091	High Similarity	NPC102414
0.9091	High Similarity	NPC220498
0.9	High Similarity	NPC107674
0.9	High Similarity	NPC470224
0.9	High Similarity	NPC307335
0.9	High Similarity	NPC141497
0.9	High Similarity	NPC136313
0.9	High Similarity	NPC275809
0.9	High Similarity	NPC474806
0.9	High Similarity	NPC74855
0.9	High Similarity	NPC133579
0.9	High Similarity	NPC170220
0.8989	High Similarity	NPC49320
0.8989	High Similarity	NPC469400
0.8989	High Similarity	NPC148414
0.8989	High Similarity	NPC175628
0.8989	High Similarity	NPC111585
0.8966	High Similarity	NPC73038
0.8901	High Similarity	NPC263548
0.8901	High Similarity	NPC32407
0.8901	High Similarity	NPC145667
0.8901	High Similarity	NPC88116
0.8901	High Similarity	NPC469406
0.8901	High Similarity	NPC20235
0.8901	High Similarity	NPC299996
0.8901	High Similarity	NPC49670
0.8901	High Similarity	NPC231063
0.8901	High Similarity	NPC282395
0.8889	High Similarity	NPC23434
0.8889	High Similarity	NPC26888
0.8889	High Similarity	NPC297265
0.8876	High Similarity	NPC128496
0.8876	High Similarity	NPC215029
0.8876	High Similarity	NPC474889
0.8876	High Similarity	NPC476733
0.8864	High Similarity	NPC138756
0.8864	High Similarity	NPC90652
0.8864	High Similarity	NPC96496
0.8864	High Similarity	NPC477926
0.883	High Similarity	NPC316964
0.8817	High Similarity	NPC108078
0.8804	High Similarity	NPC279974
0.8804	High Similarity	NPC53565
0.8804	High Similarity	NPC96916
0.8804	High Similarity	NPC45324
0.8804	High Similarity	NPC222845
0.8804	High Similarity	NPC198245
0.8804	High Similarity	NPC162001
0.8804	High Similarity	NPC32118
0.8791	High Similarity	NPC477855
0.8791	High Similarity	NPC291373
0.8764	High Similarity	NPC470417
0.8764	High Similarity	NPC182797
0.8764	High Similarity	NPC52169
0.875	High Similarity	NPC325594
0.875	High Similarity	NPC94755
0.875	High Similarity	NPC474970
0.875	High Similarity	NPC2783
0.8736	High Similarity	NPC221758
0.8736	High Similarity	NPC59453
0.8736	High Similarity	NPC165064
0.871	High Similarity	NPC204961
0.871	High Similarity	NPC25848
0.871	High Similarity	NPC230151
0.871	High Similarity	NPC19376
0.871	High Similarity	NPC259733
0.871	High Similarity	NPC73004
0.871	High Similarity	NPC173744
0.871	High Similarity	NPC158371
0.871	High Similarity	NPC207922
0.871	High Similarity	NPC201657
0.871	High Similarity	NPC173272
0.871	High Similarity	NPC307282
0.871	High Similarity	NPC305464
0.8706	High Similarity	NPC236112
0.8696	High Similarity	NPC87095
0.8696	High Similarity	NPC188102
0.8696	High Similarity	NPC166906
0.8696	High Similarity	NPC277399
0.8696	High Similarity	NPC159410
0.8681	High Similarity	NPC154101
0.8681	High Similarity	NPC155304
0.8667	High Similarity	NPC130520
0.8667	High Similarity	NPC31985
0.8667	High Similarity	NPC61543
0.8667	High Similarity	NPC263393
0.8667	High Similarity	NPC1015
0.8667	High Similarity	NPC474245
0.8667	High Similarity	NPC121798
0.8667	High Similarity	NPC143232
0.8667	High Similarity	NPC59263
0.8667	High Similarity	NPC225585
0.8667	High Similarity	NPC290972
0.8667	High Similarity	NPC127689
0.8667	High Similarity	NPC274330
0.8667	High Similarity	NPC293048
0.8667	High Similarity	NPC270768
0.8667	High Similarity	NPC25906
0.8667	High Similarity	NPC234346
0.8667	High Similarity	NPC64872
0.8667	High Similarity	NPC198664
0.866	High Similarity	NPC471293
0.8652	High Similarity	NPC475740
0.8652	High Similarity	NPC293564
0.8652	High Similarity	NPC130577
0.8652	High Similarity	NPC18064
0.8652	High Similarity	NPC269360
0.8652	High Similarity	NPC88716
0.8652	High Similarity	NPC51700
0.8652	High Similarity	NPC33768
0.8652	High Similarity	NPC98442
0.8652	High Similarity	NPC171203
0.8652	High Similarity	NPC102683
0.8652	High Similarity	NPC142415
0.8652	High Similarity	NPC68160
0.8652	High Similarity	NPC307426
0.8652	High Similarity	NPC242468
0.8652	High Similarity	NPC264005
0.8636	High Similarity	NPC264317
0.8636	High Similarity	NPC470574
0.8636	High Similarity	NPC294438
0.8632	High Similarity	NPC110149
0.8617	High Similarity	NPC9613
0.8617	High Similarity	NPC247139
0.8617	High Similarity	NPC259788
0.8617	High Similarity	NPC43686
0.8617	High Similarity	NPC261935
0.8617	High Similarity	NPC106112
0.8617	High Similarity	NPC255589
0.8605	High Similarity	NPC473420
0.8605	High Similarity	NPC474531
0.8605	High Similarity	NPC147066
0.8602	High Similarity	NPC469599
0.8602	High Similarity	NPC184848
0.8602	High Similarity	NPC48330
0.8602	High Similarity	NPC470016
0.8602	High Similarity	NPC317586
0.8602	High Similarity	NPC69548
0.8587	High Similarity	NPC475255
0.8571	High Similarity	NPC477872
0.8571	High Similarity	NPC130278
0.8571	High Similarity	NPC7260
0.8571	High Similarity	NPC273621
0.8571	High Similarity	NPC120968
0.8571	High Similarity	NPC126369
0.8571	High Similarity	NPC227467
0.8571	High Similarity	NPC111110
0.8571	High Similarity	NPC136801
0.8571	High Similarity	NPC18872
0.8571	High Similarity	NPC210037
0.8571	High Similarity	NPC290614
0.8571	High Similarity	NPC291028
0.8571	High Similarity	NPC470589
0.8556	High Similarity	NPC16377
0.8556	High Similarity	NPC471722
0.8556	High Similarity	NPC40552
0.8556	High Similarity	NPC470629
0.8556	High Similarity	NPC181225
0.8556	High Similarity	NPC193360
0.8556	High Similarity	NPC328539
0.8556	High Similarity	NPC290690
0.8556	High Similarity	NPC473242
0.8556	High Similarity	NPC17733
0.8556	High Similarity	NPC246708
0.8556	High Similarity	NPC474719
0.8556	High Similarity	NPC474512
0.8539	High Similarity	NPC474733
0.8539	High Similarity	NPC31564
0.8539	High Similarity	NPC145879
0.8539	High Similarity	NPC473168
0.8539	High Similarity	NPC72133
0.8539	High Similarity	NPC51014

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 NPC189520 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	147
0.1-0.2	1380
0.2-0.3	3929
0.3-0.4	2508
0.4-0.5	651
0.5-0.6	198
0.6-0.7	141
0.7-0.8	159
0.8-0.85	31
0.85-0.9	6
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8736	High Similarity	NPD4786	Approved
0.8667	High Similarity	NPD5328	Approved
0.8636	High Similarity	NPD7520	Clinical (unspecified phase)
0.8587	High Similarity	NPD6399	Phase 3
0.8539	High Similarity	NPD3618	Phase 1
0.8506	High Similarity	NPD3667	Approved
0.8478	Intermediate Similarity	NPD7515	Phase 2
0.8478	Intermediate Similarity	NPD6079	Approved
0.82	Intermediate Similarity	NPD5739	Approved
0.82	Intermediate Similarity	NPD6675	Approved
0.82	Intermediate Similarity	NPD6402	Approved
0.82	Intermediate Similarity	NPD7128	Approved
0.8191	Intermediate Similarity	NPD4202	Approved
0.8125	Intermediate Similarity	NPD4697	Phase 3
0.8125	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.8125	Intermediate Similarity	NPD5221	Approved
0.8125	Intermediate Similarity	NPD5222	Approved
0.8111	Intermediate Similarity	NPD3133	Approved
0.8111	Intermediate Similarity	NPD3666	Approved
0.8111	Intermediate Similarity	NPD3665	Phase 1
0.8105	Intermediate Similarity	NPD7748	Approved
0.8085	Intermediate Similarity	NPD8035	Phase 2
0.8085	Intermediate Similarity	NPD8034	Phase 2
0.8068	Intermediate Similarity	NPD7525	Registered
0.8041	Intermediate Similarity	NPD6083	Phase 2
0.8041	Intermediate Similarity	NPD4755	Approved
0.8041	Intermediate Similarity	NPD5173	Approved
0.8041	Intermediate Similarity	NPD6084	Phase 2
0.8039	Intermediate Similarity	NPD7320	Approved
0.8039	Intermediate Similarity	NPD6899	Approved
0.8039	Intermediate Similarity	NPD6881	Approved
0.8023	Intermediate Similarity	NPD6117	Approved
0.7961	Intermediate Similarity	NPD6373	Approved
0.7961	Intermediate Similarity	NPD6372	Approved
0.7959	Intermediate Similarity	NPD7638	Approved
0.7957	Intermediate Similarity	NPD6672	Approved
0.7957	Intermediate Similarity	NPD5737	Approved
0.7941	Intermediate Similarity	NPD5697	Approved
0.7941	Intermediate Similarity	NPD5701	Approved
0.7935	Intermediate Similarity	NPD6684	Approved
0.7935	Intermediate Similarity	NPD7146	Approved
0.7935	Intermediate Similarity	NPD7521	Approved
0.7935	Intermediate Similarity	NPD5330	Approved
0.7935	Intermediate Similarity	NPD6409	Approved
0.7935	Intermediate Similarity	NPD7334	Approved
0.7931	Intermediate Similarity	NPD6116	Phase 1
0.7912	Intermediate Similarity	NPD3668	Phase 3
0.7907	Intermediate Similarity	NPD7339	Approved
0.7907	Intermediate Similarity	NPD6942	Approved
0.7905	Intermediate Similarity	NPD8297	Approved
0.7885	Intermediate Similarity	NPD7102	Approved
0.7885	Intermediate Similarity	NPD7290	Approved
0.7885	Intermediate Similarity	NPD6883	Approved
0.7879	Intermediate Similarity	NPD7640	Approved
0.7879	Intermediate Similarity	NPD5286	Approved
0.7879	Intermediate Similarity	NPD7639	Approved
0.7879	Intermediate Similarity	NPD5285	Approved
0.7879	Intermediate Similarity	NPD4700	Approved
0.7879	Intermediate Similarity	NPD4696	Approved
0.7872	Intermediate Similarity	NPD4753	Phase 2
0.7864	Intermediate Similarity	NPD6011	Approved
0.7857	Intermediate Similarity	NPD7902	Approved
0.7841	Intermediate Similarity	NPD6115	Approved
0.7841	Intermediate Similarity	NPD6697	Approved
0.7841	Intermediate Similarity	NPD6118	Approved
0.7841	Intermediate Similarity	NPD6114	Approved
0.783	Intermediate Similarity	NPD4632	Approved
0.781	Intermediate Similarity	NPD6650	Approved
0.781	Intermediate Similarity	NPD6649	Approved
0.781	Intermediate Similarity	NPD6617	Approved
0.781	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.781	Intermediate Similarity	NPD6869	Approved
0.781	Intermediate Similarity	NPD8130	Phase 1
0.781	Intermediate Similarity	NPD6847	Approved
0.78	Intermediate Similarity	NPD5223	Approved
0.7791	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.7788	Intermediate Similarity	NPD6014	Approved
0.7788	Intermediate Similarity	NPD6013	Approved
0.7788	Intermediate Similarity	NPD6012	Approved
0.7778	Intermediate Similarity	NPD7115	Discovery
0.7766	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7766	Intermediate Similarity	NPD6903	Approved
0.7742	Intermediate Similarity	NPD5279	Phase 3
0.7736	Intermediate Similarity	NPD6882	Approved
0.7723	Intermediate Similarity	NPD5224	Approved
0.7723	Intermediate Similarity	NPD5211	Phase 2
0.7723	Intermediate Similarity	NPD4633	Approved
0.7723	Intermediate Similarity	NPD5226	Approved
0.7723	Intermediate Similarity	NPD5225	Approved
0.7692	Intermediate Similarity	NPD4223	Phase 3
0.7692	Intermediate Similarity	NPD4221	Approved
0.7653	Intermediate Similarity	NPD5695	Phase 3
0.7653	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD5174	Approved
0.7647	Intermediate Similarity	NPD4754	Approved
0.7647	Intermediate Similarity	NPD5175	Approved
0.7634	Intermediate Similarity	NPD5329	Approved
0.7614	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.76	Intermediate Similarity	NPD5696	Approved
0.7573	Intermediate Similarity	NPD5141	Approved
0.7553	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7553	Intermediate Similarity	NPD6098	Approved
0.7551	Intermediate Similarity	NPD7900	Approved
0.7551	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7547	Intermediate Similarity	NPD4634	Approved
0.7527	Intermediate Similarity	NPD4197	Approved
0.7526	Intermediate Similarity	NPD5281	Approved
0.7526	Intermediate Similarity	NPD5284	Approved
0.7523	Intermediate Similarity	NPD6868	Approved
0.75	Intermediate Similarity	NPD6673	Approved
0.75	Intermediate Similarity	NPD6904	Approved
0.75	Intermediate Similarity	NPD6080	Approved
0.75	Intermediate Similarity	NPD4768	Approved
0.75	Intermediate Similarity	NPD4767	Approved
0.7475	Intermediate Similarity	NPD4629	Approved
0.7475	Intermediate Similarity	NPD5210	Approved
0.7455	Intermediate Similarity	NPD6009	Approved
0.7444	Intermediate Similarity	NPD5784	Clinical (unspecified phase)
0.7429	Intermediate Similarity	NPD6412	Phase 2
0.7419	Intermediate Similarity	NPD4788	Approved
0.7416	Intermediate Similarity	NPD6933	Approved
0.7411	Intermediate Similarity	NPD6319	Approved
0.7387	Intermediate Similarity	NPD6335	Approved
0.7368	Intermediate Similarity	NPD4690	Approved
0.7368	Intermediate Similarity	NPD5205	Approved
0.7368	Intermediate Similarity	NPD4693	Phase 3
0.7368	Intermediate Similarity	NPD4689	Approved
0.7368	Intermediate Similarity	NPD4138	Approved
0.7368	Intermediate Similarity	NPD4688	Approved
0.7364	Intermediate Similarity	NPD6274	Approved
0.7363	Intermediate Similarity	NPD7645	Phase 2
0.7358	Intermediate Similarity	NPD5128	Approved
0.7358	Intermediate Similarity	NPD5168	Approved
0.7358	Intermediate Similarity	NPD4730	Approved
0.7358	Intermediate Similarity	NPD4729	Approved
0.7356	Intermediate Similarity	NPD4809	Clinical (unspecified phase)
0.7356	Intermediate Similarity	NPD4808	Clinical (unspecified phase)
0.7347	Intermediate Similarity	NPD6411	Approved
0.7333	Intermediate Similarity	NPD6008	Approved
0.7321	Intermediate Similarity	NPD7100	Approved
0.7321	Intermediate Similarity	NPD7101	Approved
0.7297	Intermediate Similarity	NPD6317	Approved
0.729	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.729	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7255	Intermediate Similarity	NPD4225	Approved
0.7253	Intermediate Similarity	NPD3617	Approved
0.7232	Intermediate Similarity	NPD6314	Approved
0.7232	Intermediate Similarity	NPD6313	Approved
0.7222	Intermediate Similarity	NPD5250	Approved
0.7222	Intermediate Similarity	NPD5248	Approved
0.7222	Intermediate Similarity	NPD5247	Approved
0.7222	Intermediate Similarity	NPD5249	Phase 3
0.7222	Intermediate Similarity	NPD5251	Approved
0.7222	Intermediate Similarity	NPD5134	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD5169	Approved
0.7222	Intermediate Similarity	NPD5135	Approved
0.7217	Intermediate Similarity	NPD7604	Phase 2
0.7216	Intermediate Similarity	NPD5208	Approved
0.7212	Intermediate Similarity	NPD7632	Discontinued
0.72	Intermediate Similarity	NPD6001	Approved
0.7193	Intermediate Similarity	NPD6909	Approved
0.7193	Intermediate Similarity	NPD5983	Phase 2
0.7193	Intermediate Similarity	NPD6908	Approved
0.7191	Intermediate Similarity	NPD6924	Approved
0.7191	Intermediate Similarity	NPD6926	Approved
0.7188	Intermediate Similarity	NPD4694	Approved
0.7188	Intermediate Similarity	NPD5690	Phase 2
0.7188	Intermediate Similarity	NPD5280	Approved
0.7172	Intermediate Similarity	NPD6050	Approved
0.7172	Intermediate Similarity	NPD5693	Phase 1
0.7159	Intermediate Similarity	NPD4243	Approved
0.7156	Intermediate Similarity	NPD5216	Approved
0.7156	Intermediate Similarity	NPD5217	Approved
0.7156	Intermediate Similarity	NPD5215	Approved
0.7156	Intermediate Similarity	NPD5127	Approved
0.7155	Intermediate Similarity	NPD7492	Approved
0.7143	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6101	Approved
0.7143	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6051	Approved
0.7126	Intermediate Similarity	NPD3699	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD3700	Clinical (unspecified phase)
0.7113	Intermediate Similarity	NPD3573	Approved
0.7105	Intermediate Similarity	NPD6054	Approved
0.7105	Intermediate Similarity	NPD6059	Approved
0.7097	Intermediate Similarity	NPD4695	Discontinued
0.7094	Intermediate Similarity	NPD6336	Discontinued
0.7094	Intermediate Similarity	NPD6616	Approved
0.7094	Intermediate Similarity	NPD7507	Approved
0.7071	Intermediate Similarity	NPD5692	Phase 3
0.7053	Intermediate Similarity	NPD5362	Discontinued
0.7045	Intermediate Similarity	NPD4747	Approved
0.7043	Intermediate Similarity	NPD6291	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD6686	Approved
0.7034	Intermediate Similarity	NPD8293	Discontinued
0.7034	Intermediate Similarity	NPD7078	Approved
0.7021	Intermediate Similarity	NPD4692	Approved
0.7021	Intermediate Similarity	NPD4139	Approved
0.7	Intermediate Similarity	NPD4785	Approved
0.7	Intermediate Similarity	NPD4784	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