NPASS Compound

Structure

NPC28532 OpenBabel07101719252D 46 50 0 0 1 0 0 0 0 0999 V2000 -3.3075 3.3496 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3379 1.5215 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3868 1.2125 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4538 -1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3305 -0.7079 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2024 1.0827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2079 0.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9474 1.6554 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6166 2.3986 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -3.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.4641 -3.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 6.9282 -3.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.6092 0.1691 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.2564 0.7044 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 6.9282 -2.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 6.0622 -1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.1962 -2.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.1962 -3.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.5947 2.1907 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5873 -0.0388 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 8.6603 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2346 0.4965 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.2638 2.9338 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3794 -1.0169 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9945 0.1045 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 30 1 0 0 0 0 3 30 1 0 0 0 0 5 32 1 0 0 0 0 7 9 1 0 0 0 0 7 17 1 0 0 0 0 8 10 1 0 0 0 0 8 24 1 0 0 0 0 9 32 1 0 0 0 0 10 34 1 0 0 0 0 11 16 1 0 0 0 0 11 25 1 0 0 0 0 12 18 2 0 0 0 0 12 20 1 0 0 0 0 13 19 1 0 0 0 0 13 22 1 0 0 0 0 14 21 1 0 0 0 0 14 31 1 0 0 0 0 15 35 1 0 0 0 0 16 1 1 6 0 0 0 16 30 1 0 0 0 0 17 18 1 0 0 0 0 17 31 1 1 0 0 0 18 34 1 0 0 0 0 19 20 1 0 0 0 0 19 31 1 6 0 0 0 20 36 2 0 0 0 0 21 22 1 0 0 0 0 21 37 1 1 0 0 0 22 45 1 1 0 0 0 23 15 1 1 0 0 0 23 26 1 0 0 0 0 23 46 1 0 0 0 0 24 32 1 1 0 0 0 24 33 1 0 0 0 0 25 33 1 0 0 0 0 25 38 1 6 0 0 0 26 27 1 0 0 0 0 26 39 1 6 0 0 0 27 28 1 0 0 0 0 27 40 1 1 0 0 0 28 29 1 0 0 0 0 28 41 1 6 0 0 0 29 45 1 1 0 0 0 29 46 1 0 0 0 0 30 42 1 0 0 0 0 31 4 1 1 0 0 0 32 34 1 1 0 0 0 33 6 1 6 0 0 0 33 43 1 0 0 0 0 34 44 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	656.38
Volume:	654.047
LogP:	1.152
LogD:	0.212
LogS:	-2.657
# Rotatable Bonds:	8
TPSA:	217.6
# H-Bond Aceptor:	12
# H-Bond Donor:	9
# Rings:	5
# Heavy Atoms:	12

MedChem Properties

QED Drug-Likeness Score:	0.159
Synthetic Accessibility Score:	5.919
Fsp3:	0.912
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.954
MDCK Permeability:	4.351027018856257e-05
Pgp-inhibitor:	0.259
Pgp-substrate:	0.832
Human Intestinal Absorption (HIA):	0.909
20% Bioavailability (F20%):	0.948
30% Bioavailability (F30%):	0.965

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.141
Plasma Protein Binding (PPB):	60.28929901123047%
Volume Distribution (VD):	0.395
Pgp-substrate:	21.068204879760742%

ADMET: Metabolism

CYP1A2-inhibitor:	0.002
CYP1A2-substrate:	0.132
CYP2C19-inhibitor:	0.002
CYP2C19-substrate:	0.447
CYP2C9-inhibitor:	0.002
CYP2C9-substrate:	0.039
CYP2D6-inhibitor:	0.0
CYP2D6-substrate:	0.022
CYP3A4-inhibitor:	0.056
CYP3A4-substrate:	0.169

ADMET: Excretion

Clearance (CL):	1.173
Half-life (T1/2):	0.717

ADMET: Toxicity

hERG Blockers:	0.08
Human Hepatotoxicity (H-HT):	0.246
Drug-inuced Liver Injury (DILI):	0.071
AMES Toxicity:	0.137
Rat Oral Acute Toxicity:	0.349
Maximum Recommended Daily Dose:	0.895
Skin Sensitization:	0.277
Carcinogencity:	0.054
Eye Corrosion:	0.003
Eye Irritation:	0.018
Respiratory Toxicity:	0.918

Download Data

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

Natural Product: NPC28532

Natural Product ID:	NPC28532
*Common Name:**	Fibraurecdyside A
IUPAC Name:	(2S,3R,5R,9R,10R,13R,14S,17S)-2,14-dihydroxy-10,13-dimethyl-17-[(2R,3R,5R)-2,3,6-trihydroxy-5,6-dimethylheptan-2-yl]-3-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2,3,4,5,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-6-one
Synonyms:
Standard InCHIKey:	MQWJGLSZBHVGLN-VBSSPFTJSA-N
Standard InCHI:	InChI=1S/C34H56O12/c1-16(30(2,3)42)11-25(38)33(6,43)24-8-10-34(44)18-12-20(36)19-13-22(45-29-28(41)27(40)26(39)23(15-35)46-29)21(37)14-31(19,4)17(18)7-9-32(24,34)5/h12,16-17,19,21-29,35,37-44H,7-11,13-15H2,1-6H3/t16-,17+,19+,21+,22-,23-,24+,25-,26-,27+,28-,29-,31-,32-,33-,34-/m1/s1
SMILES:	C[C@H](C[C@H]([C@@](C)([C@H]1CC[C@]2(C3=CC(=O)[C@@H]4C[C@H]([C@H](C[C@]4(C)[C@H]3CC[C@]12C)O)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O)O)O)O)C(C)(C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL254592
PubChem CID:	44445723
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:0002198] Pentahydroxy 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
NPO10715	Fibraurea tinctoria	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17994701]
NPO10715	Fibraurea tinctoria	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18829331]
NPO10715	Fibraurea tinctoria	Species	Menispermaceae	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
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT109	Individual Protein	Cytochrome P450 3A4	Homo sapiens	IC50	>	100000.0	nM	PMID[476030]

☑ 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 NPC28532 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	258
0.1-0.2	1576
0.2-0.3	4572
0.3-0.4	8216
0.4-0.5	11563
0.5-0.6	7408
0.6-0.7	5109
0.7-0.8	3216
0.8-0.85	636
0.85-0.9	137
0.9-0.95	5
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9286	High Similarity	NPC260665
0.9174	High Similarity	NPC471855
0.906	High Similarity	NPC202051
0.9008	High Similarity	NPC471407
0.8974	High Similarity	NPC471406
0.8947	High Similarity	NPC317210
0.8947	High Similarity	NPC962
0.8947	High Similarity	NPC250109
0.8947	High Similarity	NPC477944
0.8934	High Similarity	NPC173347
0.8926	High Similarity	NPC311534
0.8917	High Similarity	NPC174367
0.8917	High Similarity	NPC47113
0.8908	High Similarity	NPC27363
0.887	High Similarity	NPC477580
0.887	High Similarity	NPC326542
0.886	High Similarity	NPC207251
0.885	High Similarity	NPC154856
0.885	High Similarity	NPC52241
0.885	High Similarity	NPC475317
0.8843	High Similarity	NPC329784
0.8843	High Similarity	NPC152091
0.8843	High Similarity	NPC240070
0.8833	High Similarity	NPC475194
0.8833	High Similarity	NPC473505
0.8814	High Similarity	NPC129393
0.8793	High Similarity	NPC266728
0.8793	High Similarity	NPC49492
0.879	High Similarity	NPC477709
0.879	High Similarity	NPC476221
0.8783	High Similarity	NPC178981
0.878	High Similarity	NPC16569
0.878	High Similarity	NPC253456
0.878	High Similarity	NPC159338
0.8772	High Similarity	NPC285410
0.8772	High Similarity	NPC263827
0.8772	High Similarity	NPC250481
0.877	High Similarity	NPC69273
0.877	High Similarity	NPC473888
0.877	High Similarity	NPC293623
0.877	High Similarity	NPC168899
0.8761	High Similarity	NPC246205
0.876	High Similarity	NPC250556
0.876	High Similarity	NPC469750
0.875	High Similarity	NPC83744
0.874	High Similarity	NPC79250
0.874	High Similarity	NPC290746
0.8739	High Similarity	NPC42675
0.8729	High Similarity	NPC475041
0.8729	High Similarity	NPC161738
0.8718	High Similarity	NPC218970
0.871	High Similarity	NPC19124
0.871	High Similarity	NPC93416
0.871	High Similarity	NPC42670
0.8707	High Similarity	NPC74727
0.8707	High Similarity	NPC220293
0.8707	High Similarity	NPC102088
0.8699	High Similarity	NPC276838
0.8699	High Similarity	NPC232785
0.8699	High Similarity	NPC140092
0.8699	High Similarity	NPC329986
0.8699	High Similarity	NPC476966
0.8699	High Similarity	NPC125077
0.8699	High Similarity	NPC91
0.8699	High Similarity	NPC188234
0.8696	High Similarity	NPC474265
0.8696	High Similarity	NPC210420
0.8696	High Similarity	NPC130427
0.8689	High Similarity	NPC471356
0.8689	High Similarity	NPC471357
0.8689	High Similarity	NPC469757
0.8689	High Similarity	NPC146456
0.8689	High Similarity	NPC117702
0.8689	High Similarity	NPC179412
0.8684	High Similarity	NPC76084
0.8678	High Similarity	NPC318135
0.8673	High Similarity	NPC329417
0.8667	High Similarity	NPC269642
0.8661	High Similarity	NPC476027
0.8661	High Similarity	NPC150531
0.8661	High Similarity	NPC85829
0.8661	High Similarity	NPC97202
0.8661	High Similarity	NPC50692
0.8661	High Similarity	NPC214264
0.8661	High Similarity	NPC296945
0.8661	High Similarity	NPC319077
0.8661	High Similarity	NPC260268
0.8661	High Similarity	NPC302607
0.8661	High Similarity	NPC48733
0.8661	High Similarity	NPC49958
0.8661	High Similarity	NPC171137
0.8661	High Similarity	NPC152695
0.8661	High Similarity	NPC202167
0.8655	High Similarity	NPC472257
0.8644	High Similarity	NPC475632
0.8644	High Similarity	NPC45475
0.8644	High Similarity	NPC86020
0.864	High Similarity	NPC142756
0.864	High Similarity	NPC225385
0.864	High Similarity	NPC298783
0.864	High Similarity	NPC157817
0.864	High Similarity	NPC104585
0.8629	High Similarity	NPC241008
0.8621	High Similarity	NPC62696
0.8621	High Similarity	NPC293038
0.8596	High Similarity	NPC8431
0.8596	High Similarity	NPC11710
0.8595	High Similarity	NPC1980
0.8595	High Similarity	NPC238005
0.8595	High Similarity	NPC141196
0.8584	High Similarity	NPC475060
0.8584	High Similarity	NPC477916
0.8584	High Similarity	NPC220229
0.8583	High Similarity	NPC182900
0.8583	High Similarity	NPC249553
0.8571	High Similarity	NPC197003
0.8571	High Similarity	NPC319570
0.8571	High Similarity	NPC477071
0.8571	High Similarity	NPC209502
0.8571	High Similarity	NPC204833
0.8571	High Similarity	NPC190939
0.856	High Similarity	NPC231240
0.856	High Similarity	NPC473805
0.856	High Similarity	NPC473519
0.8559	High Similarity	NPC477252
0.8548	High Similarity	NPC219085
0.8548	High Similarity	NPC471359
0.8548	High Similarity	NPC471358
0.8548	High Similarity	NPC471352
0.8548	High Similarity	NPC469755
0.8548	High Similarity	NPC469754
0.8548	High Similarity	NPC471361
0.8548	High Similarity	NPC9499
0.8548	High Similarity	NPC469751
0.8548	High Similarity	NPC6108
0.8548	High Similarity	NPC180079
0.8548	High Similarity	NPC89514
0.8548	High Similarity	NPC469753
0.8548	High Similarity	NPC197707
0.8548	High Similarity	NPC86159
0.8548	High Similarity	NPC469752
0.8548	High Similarity	NPC10823
0.8548	High Similarity	NPC284406
0.8548	High Similarity	NPC17896
0.8548	High Similarity	NPC471360
0.8548	High Similarity	NPC251866
0.8548	High Similarity	NPC70542
0.8547	High Similarity	NPC474557
0.8547	High Similarity	NPC472274
0.8547	High Similarity	NPC473882
0.8537	High Similarity	NPC470882
0.8537	High Similarity	NPC305496
0.8534	High Similarity	NPC174836
0.8534	High Similarity	NPC472719
0.8534	High Similarity	NPC477253
0.8534	High Similarity	NPC207845
0.8522	High Similarity	NPC114961
0.8522	High Similarity	NPC27551
0.8522	High Similarity	NPC129340
0.8512	High Similarity	NPC222688
0.8512	High Similarity	NPC305771
0.8512	High Similarity	NPC94072
0.8512	High Similarity	NPC475431
0.8512	High Similarity	NPC15918
0.8512	High Similarity	NPC169816
0.8509	High Similarity	NPC217201
0.8509	High Similarity	NPC272576
0.85	High Similarity	NPC109973
0.85	High Similarity	NPC475187
0.85	High Similarity	NPC470312
0.85	High Similarity	NPC48692
0.8496	Intermediate Similarity	NPC210178
0.8496	Intermediate Similarity	NPC149047
0.8492	Intermediate Similarity	NPC32793
0.8492	Intermediate Similarity	NPC116075
0.8492	Intermediate Similarity	NPC316915
0.8492	Intermediate Similarity	NPC469749
0.8492	Intermediate Similarity	NPC247190
0.8492	Intermediate Similarity	NPC146857
0.8492	Intermediate Similarity	NPC102015
0.8487	Intermediate Similarity	NPC239293
0.848	Intermediate Similarity	NPC213634
0.8475	Intermediate Similarity	NPC244127
0.8475	Intermediate Similarity	NPC279638
0.8468	Intermediate Similarity	NPC477490
0.8468	Intermediate Similarity	NPC114306
0.8468	Intermediate Similarity	NPC245094
0.8462	Intermediate Similarity	NPC108721
0.8462	Intermediate Similarity	NPC200944
0.8462	Intermediate Similarity	NPC73455
0.8462	Intermediate Similarity	NPC73300
0.8455	Intermediate Similarity	NPC198714
0.8455	Intermediate Similarity	NPC93368
0.8448	Intermediate Similarity	NPC471243
0.8448	Intermediate Similarity	NPC274833
0.8448	Intermediate Similarity	NPC269466
0.8443	Intermediate Similarity	NPC41129
0.8438	Intermediate Similarity	NPC59288
0.8438	Intermediate Similarity	NPC477236
0.8435	Intermediate Similarity	NPC265655

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 NPC28532 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	225
0.1-0.2	1772
0.2-0.3	3982
0.3-0.4	2049
0.4-0.5	561
0.5-0.6	289
0.6-0.7	147
0.7-0.8	108
0.8-0.85	15
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.876	High Similarity	NPD7507	Approved
0.875	High Similarity	NPD6412	Phase 2
0.8548	High Similarity	NPD7319	Approved
0.8361	Intermediate Similarity	NPD6370	Approved
0.832	Intermediate Similarity	NPD7736	Approved
0.8264	Intermediate Similarity	NPD7516	Approved
0.824	Intermediate Similarity	NPD8293	Discontinued
0.8197	Intermediate Similarity	NPD6054	Approved
0.8197	Intermediate Similarity	NPD8377	Approved
0.8197	Intermediate Similarity	NPD8294	Approved
0.8197	Intermediate Similarity	NPD6059	Approved
0.8182	Intermediate Similarity	NPD7327	Approved
0.8182	Intermediate Similarity	NPD7328	Approved
0.8145	Intermediate Similarity	NPD8328	Phase 3
0.813	Intermediate Similarity	NPD8296	Approved
0.813	Intermediate Similarity	NPD8380	Approved
0.813	Intermediate Similarity	NPD8379	Approved
0.813	Intermediate Similarity	NPD8378	Approved
0.813	Intermediate Similarity	NPD8033	Approved
0.813	Intermediate Similarity	NPD8335	Approved
0.812	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.8067	Intermediate Similarity	NPD8297	Approved
0.8067	Intermediate Similarity	NPD6882	Approved
0.7984	Intermediate Similarity	NPD6015	Approved
0.7984	Intermediate Similarity	NPD7503	Approved
0.7984	Intermediate Similarity	NPD6016	Approved
0.7966	Intermediate Similarity	NPD6373	Approved
0.7966	Intermediate Similarity	NPD6372	Approved
0.7951	Intermediate Similarity	NPD6009	Approved
0.7937	Intermediate Similarity	NPD7492	Approved
0.792	Intermediate Similarity	NPD5988	Approved
0.7903	Intermediate Similarity	NPD6319	Approved
0.7881	Intermediate Similarity	NPD6686	Approved
0.7874	Intermediate Similarity	NPD6616	Approved
0.7863	Intermediate Similarity	NPD6675	Approved
0.7863	Intermediate Similarity	NPD6402	Approved
0.7863	Intermediate Similarity	NPD7128	Approved
0.7863	Intermediate Similarity	NPD5739	Approved
0.7851	Intermediate Similarity	NPD4632	Approved
0.7851	Intermediate Similarity	NPD8133	Approved
0.7833	Intermediate Similarity	NPD6649	Approved
0.7833	Intermediate Similarity	NPD6650	Approved
0.7812	Intermediate Similarity	NPD7078	Approved
0.7759	Intermediate Similarity	NPD5211	Phase 2
0.7731	Intermediate Similarity	NPD6899	Approved
0.7731	Intermediate Similarity	NPD7320	Approved
0.7731	Intermediate Similarity	NPD6881	Approved
0.7719	Intermediate Similarity	NPD4755	Approved
0.7686	Intermediate Similarity	NPD8130	Phase 1
0.7661	Intermediate Similarity	NPD7115	Discovery
0.7661	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD5697	Approved
0.7647	Intermediate Similarity	NPD5701	Approved
0.7627	Intermediate Similarity	NPD8170	Clinical (unspecified phase)
0.7627	Intermediate Similarity	NPD5141	Approved
0.7615	Intermediate Similarity	NPD6033	Approved
0.7603	Intermediate Similarity	NPD6883	Approved
0.7603	Intermediate Similarity	NPD7102	Approved
0.7603	Intermediate Similarity	NPD4634	Approved
0.7603	Intermediate Similarity	NPD7290	Approved
0.7586	Intermediate Similarity	NPD5286	Approved
0.7586	Intermediate Similarity	NPD5285	Approved
0.7586	Intermediate Similarity	NPD4700	Approved
0.7586	Intermediate Similarity	NPD4696	Approved
0.7578	Intermediate Similarity	NPD6067	Discontinued
0.7563	Intermediate Similarity	NPD6008	Approved
0.7559	Intermediate Similarity	NPD8515	Approved
0.7559	Intermediate Similarity	NPD8517	Approved
0.7559	Intermediate Similarity	NPD8513	Phase 3
0.7559	Intermediate Similarity	NPD8516	Approved
0.7541	Intermediate Similarity	NPD6617	Approved
0.7541	Intermediate Similarity	NPD6869	Approved
0.7541	Intermediate Similarity	NPD6847	Approved
0.7521	Intermediate Similarity	NPD6013	Approved
0.7521	Intermediate Similarity	NPD6014	Approved
0.7521	Intermediate Similarity	NPD6012	Approved
0.7458	Intermediate Similarity	NPD5224	Approved
0.7458	Intermediate Similarity	NPD5225	Approved
0.7458	Intermediate Similarity	NPD5226	Approved
0.7458	Intermediate Similarity	NPD4633	Approved
0.7442	Intermediate Similarity	NPD7604	Phase 2
0.7438	Intermediate Similarity	NPD6011	Approved
0.7436	Intermediate Similarity	NPD7640	Approved
0.7436	Intermediate Similarity	NPD7639	Approved
0.7422	Intermediate Similarity	NPD5983	Phase 2
0.7417	Intermediate Similarity	NPD4767	Approved
0.7417	Intermediate Similarity	NPD4768	Approved
0.7411	Intermediate Similarity	NPD5328	Approved
0.7398	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7395	Intermediate Similarity	NPD5175	Approved
0.7395	Intermediate Similarity	NPD5174	Approved
0.7373	Intermediate Similarity	NPD5223	Approved
0.7368	Intermediate Similarity	NPD4202	Approved
0.735	Intermediate Similarity	NPD7638	Approved
0.7328	Intermediate Similarity	NPD6336	Discontinued
0.7295	Intermediate Similarity	NPD4730	Approved
0.7295	Intermediate Similarity	NPD4729	Approved
0.7281	Intermediate Similarity	NPD6079	Approved
0.7265	Intermediate Similarity	NPD6083	Phase 2
0.7265	Intermediate Similarity	NPD6084	Phase 2
0.725	Intermediate Similarity	NPD4754	Approved
0.7236	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD4697	Phase 3
0.7177	Intermediate Similarity	NPD5251	Approved
0.7177	Intermediate Similarity	NPD5250	Approved
0.7177	Intermediate Similarity	NPD5248	Approved
0.7177	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7177	Intermediate Similarity	NPD5247	Approved
0.7177	Intermediate Similarity	NPD5249	Phase 3
0.7165	Intermediate Similarity	NPD6274	Approved
0.7154	Intermediate Similarity	NPD5128	Approved
0.7154	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD3618	Phase 1
0.7132	Intermediate Similarity	NPD7101	Approved
0.7132	Intermediate Similarity	NPD7100	Approved
0.7119	Intermediate Similarity	NPD7902	Approved
0.7105	Intermediate Similarity	NPD4753	Phase 2
0.7069	Intermediate Similarity	NPD6399	Phase 3
0.7063	Intermediate Similarity	NPD6053	Discontinued
0.7059	Intermediate Similarity	NPD5696	Approved
0.7054	Intermediate Similarity	NPD6335	Approved
0.7034	Intermediate Similarity	NPD5221	Approved
0.7034	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7034	Intermediate Similarity	NPD5222	Approved
0.7023	Intermediate Similarity	NPD6909	Approved
0.7023	Intermediate Similarity	NPD6908	Approved
0.7009	Intermediate Similarity	NPD7748	Approved
0.6984	Remote Similarity	NPD5217	Approved
0.6984	Remote Similarity	NPD5216	Approved
0.6984	Remote Similarity	NPD5215	Approved
0.6977	Remote Similarity	NPD6317	Approved
0.6975	Remote Similarity	NPD5173	Approved
0.6964	Remote Similarity	NPD3665	Phase 1
0.6964	Remote Similarity	NPD3666	Approved
0.6964	Remote Similarity	NPD3133	Approved
0.6949	Remote Similarity	NPD5210	Approved
0.6949	Remote Similarity	NPD4629	Approved
0.6949	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6949	Remote Similarity	NPD5695	Phase 3
0.6935	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD6314	Approved
0.6923	Remote Similarity	NPD6313	Approved
0.6905	Remote Similarity	NPD5169	Approved
0.6905	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD5135	Approved
0.6894	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6889	Remote Similarity	NPD8074	Phase 3
0.6885	Remote Similarity	NPD7632	Discontinued
0.687	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6864	Remote Similarity	NPD7900	Approved
0.6864	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6861	Remote Similarity	NPD5956	Approved
0.685	Remote Similarity	NPD5127	Approved
0.685	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD5330	Approved
0.6842	Remote Similarity	NPD7521	Approved
0.6842	Remote Similarity	NPD6684	Approved
0.6842	Remote Similarity	NPD7146	Approved
0.6842	Remote Similarity	NPD7334	Approved
0.6842	Remote Similarity	NPD6409	Approved
0.6838	Remote Similarity	NPD8035	Phase 2
0.6838	Remote Similarity	NPD8034	Phase 2
0.6838	Remote Similarity	NPD7515	Phase 2
0.6814	Remote Similarity	NPD4786	Approved
0.6786	Remote Similarity	NPD4221	Approved
0.6786	Remote Similarity	NPD4223	Phase 3
0.678	Remote Similarity	NPD8171	Discontinued
0.6777	Remote Similarity	NPD4225	Approved
0.6772	Remote Similarity	NPD6371	Approved
0.6754	Remote Similarity	NPD5329	Approved
0.6735	Remote Similarity	NPD7625	Phase 1
0.6724	Remote Similarity	NPD6903	Approved
0.6696	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6695	Remote Similarity	NPD5281	Approved
0.6695	Remote Similarity	NPD5284	Approved
0.6692	Remote Similarity	NPD5167	Approved
0.6667	Remote Similarity	NPD6904	Approved
0.6667	Remote Similarity	NPD6080	Approved
0.6667	Remote Similarity	NPD4197	Approved
0.6667	Remote Similarity	NPD6673	Approved
0.6643	Remote Similarity	NPD8338	Approved
0.6642	Remote Similarity	NPD6921	Approved
0.6641	Remote Similarity	NPD6868	Approved
0.6638	Remote Similarity	NPD7524	Approved
0.6638	Remote Similarity	NPD3573	Approved
0.6637	Remote Similarity	NPD3667	Approved
0.6605	Remote Similarity	NPD7799	Discontinued
0.6594	Remote Similarity	NPD8336	Approved
0.6594	Remote Similarity	NPD8337	Approved
0.6583	Remote Similarity	NPD6001	Approved
0.6581	Remote Similarity	NPD5737	Approved
0.6581	Remote Similarity	NPD6672	Approved
0.6571	Remote Similarity	NPD7260	Phase 2
0.6555	Remote Similarity	NPD5693	Phase 1
0.6552	Remote Similarity	NPD4138	Approved
0.6552	Remote Similarity	NPD4688	Approved
0.6552	Remote Similarity	NPD4693	Phase 3
0.6552	Remote Similarity	NPD5205	Approved
0.6552	Remote Similarity	NPD4689	Approved
0.6552	Remote Similarity	NPD4690	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