NPASS Compound

Structure

NPC470054 OpenBabel07101718322D 39 43 0 0 1 0 0 0 0 0999 V2000 7.3386 -3.8023 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.3386 -0.8023 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.8386 0.0638 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5983 0.8443 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9292 0.1011 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4207 -0.1113 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7405 -1.3023 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7405 1.6977 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6720 2.2804 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6666 2.1759 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8745 -0.8023 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4726 -2.3023 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0085 -0.3023 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6065 -1.8023 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6180 1.9021 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4726 0.6977 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9781 0.2079 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.2046 -3.3023 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2872 1.1590 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.2653 1.3669 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.8745 1.1977 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7405 -0.3023 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 6.4726 -0.3023 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.6065 1.1977 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.3601 1.6942 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 7.3386 -1.8023 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 7.3386 -0.8023 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6202 1.0522 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0085 0.6977 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.6065 -0.8023 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.7405 0.6977 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.6691 0.7431 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 9.0706 -3.8023 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.6065 2.1977 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0292 2.4373 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.8281 2.0303 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.4123 0.0740 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 8.2046 -2.3023 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 18 1 0 0 0 0 2 27 1 0 0 0 0 3 27 1 0 0 0 0 4 28 1 0 0 0 0 5 28 1 0 0 0 0 9 10 1 0 0 0 0 9 20 1 0 0 0 0 10 21 2 0 0 0 0 11 13 1 0 0 0 0 11 22 1 0 0 0 0 12 14 1 0 0 0 0 12 26 1 0 0 0 0 13 29 1 0 0 0 0 14 30 1 0 0 0 0 15 25 1 0 0 0 0 16 23 1 0 0 0 0 16 24 1 0 0 0 0 17 19 1 0 0 0 0 17 38 1 0 0 0 0 18 33 2 0 0 0 0 18 39 1 0 0 0 0 19 15 1 1 0 0 0 19 20 1 0 0 0 0 20 29 1 1 0 0 0 21 29 1 0 0 0 0 21 31 1 0 0 0 0 22 30 1 1 0 0 0 22 31 1 0 0 0 0 23 27 1 0 0 0 0 23 30 1 1 0 0 0 24 31 1 6 0 0 0 24 34 1 0 0 0 0 25 32 1 6 0 0 0 25 35 1 0 0 0 0 26 27 1 0 0 0 0 26 39 1 6 0 0 0 28 32 1 0 0 0 0 28 36 1 0 0 0 0 29 6 1 6 0 0 0 30 7 1 1 0 0 0 31 8 1 1 0 0 0 32 37 1 1 0 0 0 32 38 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	548.37
Volume:	575.504
LogP:	3.665
LogD:	3.08
LogS:	-4.15
# Rotatable Bonds:	4
TPSA:	116.45
# H-Bond Aceptor:	7
# H-Bond Donor:	4
# Rings:	5
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.306
Synthetic Accessibility Score:	5.458
Fsp3:	0.906
Lipinski Rule-of-5:	Accepted
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:	-5.103
MDCK Permeability:	1.1976056157436687e-05
Pgp-inhibitor:	0.986
Pgp-substrate:	0.035
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.018
30% Bioavailability (F30%):	0.708

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.117
Plasma Protein Binding (PPB):	87.21526336669922%
Volume Distribution (VD):	0.853
Pgp-substrate:	8.290641784667969%

ADMET: Metabolism

CYP1A2-inhibitor:	0.003
CYP1A2-substrate:	0.104
CYP2C19-inhibitor:	0.008
CYP2C19-substrate:	0.771
CYP2C9-inhibitor:	0.045
CYP2C9-substrate:	0.057
CYP2D6-inhibitor:	0.005
CYP2D6-substrate:	0.077
CYP3A4-inhibitor:	0.333
CYP3A4-substrate:	0.283

ADMET: Excretion

Clearance (CL):	2.346
Half-life (T1/2):	0.349

ADMET: Toxicity

hERG Blockers:	0.042
Human Hepatotoxicity (H-HT):	0.403
Drug-inuced Liver Injury (DILI):	0.102
AMES Toxicity:	0.022
Rat Oral Acute Toxicity:	0.055
Maximum Recommended Daily Dose:	0.868
Skin Sensitization:	0.264
Carcinogencity:	0.012
Eye Corrosion:	0.003
Eye Irritation:	0.015
Respiratory Toxicity:	0.95

Download Data

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

Natural Product: NPC470054

Natural Product ID:	NPC470054
*Common Name:**	Chisopanin B
IUPAC Name:	[(3R,5R,7R,8R,9R,10S,13S,17R)-17-[(3S,5R,6S)-5,6-dihydroxy-6-(2-hydroxypropan-2-yl)oxan-3-yl]-7-hydroxy-4,4,8,10,13-pentamethyl-2,3,5,6,7,9,11,12,16,17-decahydro-1H-cyclopenta[a]phenanthren-3-yl] acetate
Synonyms:	Chisopanin B
Standard InCHIKey:	JDKVVJZONYEUFM-MORBJWPESA-N
Standard InCHI:	InChI=1S/C32H52O7/c1-18(33)39-26-12-14-30(7)22-11-13-29(6)20(19-15-25(35)32(37,38-17-19)28(4,5)36)9-10-21(29)31(22,8)24(34)16-23(30)27(26,2)3/h10,19-20,22-26,34-37H,9,11-17H2,1-8H3/t19-,20-,22-,23+,24-,25-,26-,29+,30-,31+,32+/m1/s1
SMILES:	CC(=O)O[C@@H]1CC[C@]2([C@H](C1(C)C)C[C@H]([C@@]1([C@@H]2CC[C@@]2(C1=CC[C@@H]2[C@H]1CO[C@]([C@@H](C1)O)(O)C(O)(C)C)C)C)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1668607
PubChem CID:	53323602
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids

*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
NPO19151	Chisocheton paniculatus	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19943621]
NPO19151	Chisocheton paniculatus	Species	Meliaceae	Eukaryota	twigs	Xishuangbanna, Yunnan, China	2007-May	PMID[21288727]
NPO19151	Chisocheton paniculatus	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32208696]
NPO19151	Chisocheton paniculatus	Species	Meliaceae	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
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	7900.0	nM	PMID[516080]
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	30700.0	nM	PMID[516080]

☑ 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 NPC470054 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	233
0.1-0.2	1683
0.2-0.3	5009
0.3-0.4	12155
0.4-0.5	10374
0.5-0.6	5537
0.6-0.7	4609
0.7-0.8	2534
0.8-0.85	528
0.85-0.9	30
0.9-0.95	2
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9894	High Similarity	NPC470053
0.9785	High Similarity	NPC470068
0.9368	High Similarity	NPC470067
0.9368	High Similarity	NPC470066
0.9286	High Similarity	NPC470043
0.9286	High Similarity	NPC470064
0.9286	High Similarity	NPC470058
0.9286	High Similarity	NPC470057
0.9286	High Similarity	NPC470059
0.9286	High Similarity	NPC470060
0.9286	High Similarity	NPC470062
0.9286	High Similarity	NPC470061
0.9192	High Similarity	NPC473199
0.901	High Similarity	NPC38217
0.901	High Similarity	NPC472988
0.8922	High Similarity	NPC296761
0.8922	High Similarity	NPC218853
0.8922	High Similarity	NPC154085
0.8922	High Similarity	NPC125361
0.8922	High Similarity	NPC43976
0.8922	High Similarity	NPC51925
0.8911	High Similarity	NPC234160
0.8889	High Similarity	NPC136816
0.8835	High Similarity	NPC250956
0.8812	High Similarity	NPC470055
0.8812	High Similarity	NPC470056
0.8788	High Similarity	NPC472023
0.8788	High Similarity	NPC160734
0.8788	High Similarity	NPC47566
0.8788	High Similarity	NPC88000
0.8788	High Similarity	NPC129372
0.8788	High Similarity	NPC155974
0.8788	High Similarity	NPC309425
0.8788	High Similarity	NPC4831
0.8776	High Similarity	NPC476895
0.8776	High Similarity	NPC234287
0.8776	High Similarity	NPC280825
0.875	High Similarity	NPC114188
0.875	High Similarity	NPC65167
0.8713	High Similarity	NPC31430
0.8713	High Similarity	NPC85593
0.87	High Similarity	NPC154452
0.8687	High Similarity	NPC7341
0.8687	High Similarity	NPC473200
0.8687	High Similarity	NPC208358
0.8673	High Similarity	NPC476893
0.8627	High Similarity	NPC472898
0.8627	High Similarity	NPC472899
0.8627	High Similarity	NPC472900
0.8614	High Similarity	NPC286969
0.8614	High Similarity	NPC120123
0.8614	High Similarity	NPC131479
0.8614	High Similarity	NPC473198
0.8614	High Similarity	NPC155010
0.8614	High Similarity	NPC31907
0.8614	High Similarity	NPC8039
0.8614	High Similarity	NPC211879
0.8614	High Similarity	NPC472252
0.8614	High Similarity	NPC157659
0.8614	High Similarity	NPC245280
0.8614	High Similarity	NPC16520
0.8614	High Similarity	NPC189852
0.8614	High Similarity	NPC473020
0.8614	High Similarity	NPC213190
0.8614	High Similarity	NPC114874
0.86	High Similarity	NPC21064
0.86	High Similarity	NPC476896
0.86	High Similarity	NPC121072
0.8586	High Similarity	NPC477876
0.8586	High Similarity	NPC477928
0.8586	High Similarity	NPC102426
0.8586	High Similarity	NPC477875
0.8586	High Similarity	NPC300179
0.8585	High Similarity	NPC144068
0.8585	High Similarity	NPC255017
0.8571	High Similarity	NPC471903
0.8571	High Similarity	NPC304899
0.8571	High Similarity	NPC253115
0.8557	High Similarity	NPC211238
0.8529	High Similarity	NPC221562
0.8529	High Similarity	NPC173583
0.8529	High Similarity	NPC165033
0.8529	High Similarity	NPC273879
0.8529	High Similarity	NPC470885
0.8529	High Similarity	NPC187400
0.8515	High Similarity	NPC159036
0.8515	High Similarity	NPC312553
0.8515	High Similarity	NPC288694
0.85	High Similarity	NPC473790
0.85	High Similarity	NPC317019
0.85	High Similarity	NPC282669
0.8485	Intermediate Similarity	NPC475032
0.8485	Intermediate Similarity	NPC473555
0.8485	Intermediate Similarity	NPC278939
0.8485	Intermediate Similarity	NPC475033
0.8485	Intermediate Similarity	NPC473890
0.8485	Intermediate Similarity	NPC243728
0.8485	Intermediate Similarity	NPC471770
0.8462	Intermediate Similarity	NPC295389
0.8462	Intermediate Similarity	NPC295980
0.8447	Intermediate Similarity	NPC160816
0.8447	Intermediate Similarity	NPC152584
0.8447	Intermediate Similarity	NPC208477
0.8447	Intermediate Similarity	NPC165405
0.8447	Intermediate Similarity	NPC470763
0.8447	Intermediate Similarity	NPC69737
0.8447	Intermediate Similarity	NPC472655
0.8447	Intermediate Similarity	NPC208594
0.8447	Intermediate Similarity	NPC127801
0.8447	Intermediate Similarity	NPC470767
0.8447	Intermediate Similarity	NPC269627
0.8447	Intermediate Similarity	NPC194842
0.8431	Intermediate Similarity	NPC16573
0.8431	Intermediate Similarity	NPC475701
0.8431	Intermediate Similarity	NPC474124
0.8426	Intermediate Similarity	NPC146652
0.8416	Intermediate Similarity	NPC476132
0.8416	Intermediate Similarity	NPC475617
0.8416	Intermediate Similarity	NPC289670
0.84	Intermediate Similarity	NPC157739
0.84	Intermediate Similarity	NPC158088
0.8396	Intermediate Similarity	NPC263827
0.8396	Intermediate Similarity	NPC250481
0.8396	Intermediate Similarity	NPC285410
0.8384	Intermediate Similarity	NPC472989
0.8381	Intermediate Similarity	NPC477070
0.8381	Intermediate Similarity	NPC472901
0.8381	Intermediate Similarity	NPC477069
0.8367	Intermediate Similarity	NPC178949
0.8367	Intermediate Similarity	NPC96736
0.8365	Intermediate Similarity	NPC473469
0.8365	Intermediate Similarity	NPC14946
0.8365	Intermediate Similarity	NPC208650
0.8365	Intermediate Similarity	NPC190395
0.8365	Intermediate Similarity	NPC231340
0.8365	Intermediate Similarity	NPC181467
0.8365	Intermediate Similarity	NPC63368
0.8364	Intermediate Similarity	NPC5883
0.8364	Intermediate Similarity	NPC268326
0.8364	Intermediate Similarity	NPC29639
0.8364	Intermediate Similarity	NPC304260
0.8364	Intermediate Similarity	NPC44899
0.8364	Intermediate Similarity	NPC153085
0.8351	Intermediate Similarity	NPC219516
0.835	Intermediate Similarity	NPC470768
0.835	Intermediate Similarity	NPC474464
0.835	Intermediate Similarity	NPC473543
0.835	Intermediate Similarity	NPC75608
0.835	Intermediate Similarity	NPC152966
0.835	Intermediate Similarity	NPC471111
0.8349	Intermediate Similarity	NPC93883
0.8333	Intermediate Similarity	NPC472274
0.8333	Intermediate Similarity	NPC69576
0.8333	Intermediate Similarity	NPC177701
0.8333	Intermediate Similarity	NPC475344
0.8333	Intermediate Similarity	NPC84949
0.8333	Intermediate Similarity	NPC31085
0.8333	Intermediate Similarity	NPC476471
0.8333	Intermediate Similarity	NPC471633
0.8333	Intermediate Similarity	NPC473882
0.8333	Intermediate Similarity	NPC31354
0.8318	Intermediate Similarity	NPC46388
0.8318	Intermediate Similarity	NPC37739
0.8317	Intermediate Similarity	NPC474571
0.8317	Intermediate Similarity	NPC476195
0.8317	Intermediate Similarity	NPC254567
0.8317	Intermediate Similarity	NPC473510
0.8302	Intermediate Similarity	NPC475317
0.8302	Intermediate Similarity	NPC470065
0.8302	Intermediate Similarity	NPC154856
0.8302	Intermediate Similarity	NPC129340
0.8302	Intermediate Similarity	NPC101450
0.8302	Intermediate Similarity	NPC52241
0.8302	Intermediate Similarity	NPC274507
0.8286	Intermediate Similarity	NPC472896
0.8286	Intermediate Similarity	NPC180183
0.8286	Intermediate Similarity	NPC472897
0.8286	Intermediate Similarity	NPC258323
0.8286	Intermediate Similarity	NPC6931
0.8286	Intermediate Similarity	NPC7213
0.8286	Intermediate Similarity	NPC220427
0.8286	Intermediate Similarity	NPC246124
0.8286	Intermediate Similarity	NPC159005
0.8283	Intermediate Similarity	NPC473415
0.8283	Intermediate Similarity	NPC37787
0.8283	Intermediate Similarity	NPC469329
0.8283	Intermediate Similarity	NPC30677
0.8283	Intermediate Similarity	NPC180557
0.8283	Intermediate Similarity	NPC476894
0.8273	Intermediate Similarity	NPC472080
0.8269	Intermediate Similarity	NPC474015
0.8269	Intermediate Similarity	NPC242748
0.8269	Intermediate Similarity	NPC309448
0.8257	Intermediate Similarity	NPC199428
0.8257	Intermediate Similarity	NPC212660
0.8257	Intermediate Similarity	NPC99620
0.8257	Intermediate Similarity	NPC5311
0.8257	Intermediate Similarity	NPC310341
0.8257	Intermediate Similarity	NPC193382
0.8252	Intermediate Similarity	NPC471467

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 NPC470054 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	194
0.1-0.2	1925
0.2-0.3	3952
0.3-0.4	2023
0.4-0.5	619
0.5-0.6	275
0.6-0.7	130
0.7-0.8	32
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8214	Intermediate Similarity	NPD8033	Approved
0.8125	Intermediate Similarity	NPD8377	Approved
0.8125	Intermediate Similarity	NPD8294	Approved
0.8108	Intermediate Similarity	NPD7328	Approved
0.8108	Intermediate Similarity	NPD7327	Approved
0.8053	Intermediate Similarity	NPD8379	Approved
0.8053	Intermediate Similarity	NPD8378	Approved
0.8053	Intermediate Similarity	NPD8335	Approved
0.8053	Intermediate Similarity	NPD8380	Approved
0.8053	Intermediate Similarity	NPD8296	Approved
0.8036	Intermediate Similarity	NPD7516	Approved
0.7706	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7627	Intermediate Similarity	NPD7507	Approved
0.7589	Intermediate Similarity	NPD8133	Approved
0.7586	Intermediate Similarity	NPD7503	Approved
0.7579	Intermediate Similarity	NPD7525	Registered
0.7544	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7524	Intermediate Similarity	NPD7638	Approved
0.7523	Intermediate Similarity	NPD6412	Phase 2
0.7453	Intermediate Similarity	NPD7639	Approved
0.7453	Intermediate Similarity	NPD7640	Approved
0.7438	Intermediate Similarity	NPD7319	Approved
0.7355	Intermediate Similarity	NPD7736	Approved
0.7311	Intermediate Similarity	NPD8328	Phase 3
0.7297	Intermediate Similarity	NPD6686	Approved
0.7282	Intermediate Similarity	NPD8035	Phase 2
0.7282	Intermediate Similarity	NPD8034	Phase 2
0.7228	Intermediate Similarity	NPD7524	Approved
0.7212	Intermediate Similarity	NPD6399	Phase 3
0.7193	Intermediate Similarity	NPD8297	Approved
0.7143	Intermediate Similarity	NPD7748	Approved
0.7131	Intermediate Similarity	NPD8293	Discontinued
0.713	Intermediate Similarity	NPD4632	Approved
0.7117	Intermediate Similarity	NPD7128	Approved
0.7117	Intermediate Similarity	NPD5739	Approved
0.7117	Intermediate Similarity	NPD6675	Approved
0.7117	Intermediate Similarity	NPD6402	Approved
0.7113	Intermediate Similarity	NPD7645	Phase 2
0.7107	Intermediate Similarity	NPD7492	Approved
0.7103	Intermediate Similarity	NPD7902	Approved
0.71	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.7094	Intermediate Similarity	NPD7115	Discovery
0.7094	Intermediate Similarity	NPD6009	Approved
0.708	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD6319	Approved
0.7059	Intermediate Similarity	NPD6054	Approved
0.7059	Intermediate Similarity	NPD6059	Approved
0.7049	Intermediate Similarity	NPD6616	Approved
0.7048	Intermediate Similarity	NPD8171	Discontinued
0.7043	Intermediate Similarity	NPD6882	Approved
0.7037	Intermediate Similarity	NPD4225	Approved
0.703	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD6695	Phase 3
0.7	Intermediate Similarity	NPD7632	Discontinued
0.6992	Remote Similarity	NPD7078	Approved
0.6991	Remote Similarity	NPD6899	Approved
0.6991	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6991	Remote Similarity	NPD6881	Approved
0.6991	Remote Similarity	NPD7320	Approved
0.6957	Remote Similarity	NPD8130	Phase 1
0.6952	Remote Similarity	NPD7515	Phase 2
0.6942	Remote Similarity	NPD6370	Approved
0.693	Remote Similarity	NPD6372	Approved
0.693	Remote Similarity	NPD6373	Approved
0.6909	Remote Similarity	NPD5344	Discontinued
0.6903	Remote Similarity	NPD5701	Approved
0.6903	Remote Similarity	NPD5697	Approved
0.6893	Remote Similarity	NPD7750	Discontinued
0.6875	Remote Similarity	NPD7339	Approved
0.6875	Remote Similarity	NPD6942	Approved
0.687	Remote Similarity	NPD6883	Approved
0.687	Remote Similarity	NPD7290	Approved
0.687	Remote Similarity	NPD7102	Approved
0.6869	Remote Similarity	NPD6928	Phase 2
0.686	Remote Similarity	NPD6015	Approved
0.686	Remote Similarity	NPD6016	Approved
0.6822	Remote Similarity	NPD7900	Approved
0.6822	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6814	Remote Similarity	NPD6008	Approved
0.681	Remote Similarity	NPD6869	Approved
0.681	Remote Similarity	NPD6847	Approved
0.681	Remote Similarity	NPD6650	Approved
0.681	Remote Similarity	NPD6649	Approved
0.681	Remote Similarity	NPD6617	Approved
0.6804	Remote Similarity	NPD6933	Approved
0.6803	Remote Similarity	NPD5988	Approved
0.6792	Remote Similarity	NPD7637	Suspended
0.6789	Remote Similarity	NPD6084	Phase 2
0.6789	Remote Similarity	NPD6083	Phase 2
0.6783	Remote Similarity	NPD6012	Approved
0.6783	Remote Similarity	NPD6013	Approved
0.6783	Remote Similarity	NPD6014	Approved
0.6765	Remote Similarity	NPD4786	Approved
0.6748	Remote Similarity	NPD7604	Phase 2
0.6726	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6724	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6721	Remote Similarity	NPD8517	Approved
0.6721	Remote Similarity	NPD8515	Approved
0.6721	Remote Similarity	NPD8516	Approved
0.6721	Remote Similarity	NPD5983	Phase 2
0.6721	Remote Similarity	NPD8513	Phase 3
0.6702	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.67	Remote Similarity	NPD7509	Discontinued
0.67	Remote Similarity	NPD6931	Approved
0.67	Remote Similarity	NPD6930	Phase 2
0.6696	Remote Similarity	NPD6011	Approved
0.6667	Remote Similarity	NPD6115	Approved
0.6667	Remote Similarity	NPD6697	Approved
0.6667	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6114	Approved
0.6667	Remote Similarity	NPD6118	Approved
0.664	Remote Similarity	NPD6336	Discontinued
0.6636	Remote Similarity	NPD4755	Approved
0.6633	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6604	Remote Similarity	NPD5328	Approved
0.6604	Remote Similarity	NPD6051	Approved
0.66	Remote Similarity	NPD6929	Approved
0.6598	Remote Similarity	NPD6926	Approved
0.6598	Remote Similarity	NPD6924	Approved
0.6581	Remote Similarity	NPD4634	Approved
0.6574	Remote Similarity	NPD4202	Approved
0.6571	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6569	Remote Similarity	NPD3667	Approved
0.6566	Remote Similarity	NPD6116	Phase 1
0.6566	Remote Similarity	NPD6932	Approved
0.6542	Remote Similarity	NPD3168	Discontinued
0.6535	Remote Similarity	NPD6033	Approved
0.6535	Remote Similarity	NPD7332	Phase 2
0.6518	Remote Similarity	NPD5285	Approved
0.6518	Remote Similarity	NPD6648	Approved
0.6518	Remote Similarity	NPD5286	Approved
0.6518	Remote Similarity	NPD4700	Approved
0.6518	Remote Similarity	NPD4696	Approved
0.6509	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6481	Remote Similarity	NPD6079	Approved
0.6481	Remote Similarity	NPD7087	Discontinued
0.6481	Remote Similarity	NPD6411	Approved
0.648	Remote Similarity	NPD6067	Discontinued
0.6476	Remote Similarity	NPD3618	Phase 1
0.6471	Remote Similarity	NPD6898	Phase 1
0.6466	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6465	Remote Similarity	NPD6117	Approved
0.6462	Remote Similarity	NPD8449	Approved
0.6455	Remote Similarity	NPD5695	Phase 3
0.6449	Remote Similarity	NPD7625	Phase 1
0.6446	Remote Similarity	NPD6274	Approved
0.6436	Remote Similarity	NPD6683	Phase 2
0.6429	Remote Similarity	NPD5696	Approved
0.6429	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6423	Remote Similarity	NPD7101	Approved
0.6423	Remote Similarity	NPD7100	Approved
0.6412	Remote Similarity	NPD8450	Suspended
0.6404	Remote Similarity	NPD5224	Approved
0.6404	Remote Similarity	NPD5211	Phase 2
0.6404	Remote Similarity	NPD5225	Approved
0.6404	Remote Similarity	NPD4633	Approved
0.6404	Remote Similarity	NPD5226	Approved
0.64	Remote Similarity	NPD5776	Phase 2
0.64	Remote Similarity	NPD6925	Approved
0.6389	Remote Similarity	NPD6698	Approved
0.6389	Remote Similarity	NPD7838	Discovery
0.6389	Remote Similarity	NPD46	Approved
0.6381	Remote Similarity	NPD6893	Approved
0.6373	Remote Similarity	NPD7514	Phase 3
0.6373	Remote Similarity	NPD4748	Discontinued
0.6355	Remote Similarity	NPD5737	Approved
0.6355	Remote Similarity	NPD6672	Approved
0.6348	Remote Similarity	NPD5174	Approved
0.6348	Remote Similarity	NPD5175	Approved
0.6341	Remote Similarity	NPD6335	Approved
0.6337	Remote Similarity	NPD7145	Approved
0.6333	Remote Similarity	NPD6053	Discontinued
0.6328	Remote Similarity	NPD8074	Phase 3
0.6321	Remote Similarity	NPD6409	Approved
0.6321	Remote Similarity	NPD7521	Approved
0.6321	Remote Similarity	NPD5330	Approved
0.6321	Remote Similarity	NPD7146	Approved
0.6321	Remote Similarity	NPD6684	Approved
0.6321	Remote Similarity	NPD7334	Approved
0.632	Remote Similarity	NPD6921	Approved
0.632	Remote Similarity	NPD6909	Approved
0.632	Remote Similarity	NPD6908	Approved
0.6316	Remote Similarity	NPD5223	Approved
0.6316	Remote Similarity	NPD4159	Approved
0.6311	Remote Similarity	NPD6940	Discontinued
0.6306	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6303	Remote Similarity	NPD6371	Approved
0.6296	Remote Similarity	NPD4753	Phase 2
0.6296	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6296	Remote Similarity	NPD6101	Approved
0.6293	Remote Similarity	NPD5141	Approved
0.6263	Remote Similarity	NPD4785	Approved
0.6263	Remote Similarity	NPD4784	Approved
0.6263	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6262	Remote Similarity	NPD3573	Approved
0.626	Remote Similarity	NPD6317	Approved
0.625	Remote Similarity	NPD4697	Phase 3
0.625	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.625	Remote Similarity	NPD5222	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