NPASS Compound

Structure

NPC163314 OpenBabel07101718182D 32 37 0 0 1 0 0 0 0 0999 V2000 -2.4271 -2.7634 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2601 -2.2601 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0880 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8966 -1.1045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2219 2.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3559 2.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7226 -1.1810 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9135 -0.5933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9540 2.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5388 1.1180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2219 -0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9540 0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7045 -2.5823 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6180 -2.1756 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.9511 -1.3090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.0880 2.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3559 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2219 0.8090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.4899 0.8090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 6.8200 2.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8200 1.3090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.9511 0.3090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.3559 -0.6910 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.5388 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.0880 1.3090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.4899 -0.1910 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 7.6861 2.8090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.6861 0.8090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3559 -1.6910 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.1045 -1.9945 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 2 15 1 0 0 0 0 5 6 1 0 0 0 0 5 16 1 0 0 0 0 6 17 2 0 0 0 0 7 8 1 0 0 0 0 7 14 1 0 0 0 0 9 16 2 0 0 0 0 9 20 1 0 0 0 0 10 19 1 0 0 0 0 11 18 1 0 0 0 0 11 23 1 0 0 0 0 12 21 1 0 0 0 0 12 25 1 0 0 0 0 13 14 1 0 0 0 0 13 31 1 0 0 0 0 14 1 1 6 0 0 0 15 24 1 0 0 0 0 15 27 1 6 0 0 0 16 25 1 0 0 0 0 17 18 1 0 0 0 0 17 19 1 0 0 0 0 18 25 1 1 0 0 0 19 26 1 1 0 0 0 20 21 1 0 0 0 0 20 28 2 0 0 0 0 21 29 1 1 0 0 0 22 10 1 1 0 0 0 22 24 1 0 0 0 0 22 32 1 0 0 0 0 23 26 1 6 0 0 0 23 30 1 0 0 0 0 24 26 1 1 0 0 0 25 3 1 1 0 0 0 26 4 1 1 0 0 0 27 8 1 1 0 0 0 27 31 1 0 0 0 0 27 32 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	442.27
Volume:	460.251
LogP:	4.016
LogD:	3.492
LogS:	-5.378
# Rotatable Bonds:	0
TPSA:	72.83
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	6
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.452
Synthetic Accessibility Score:	5.778
Fsp3:	0.852
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.783
MDCK Permeability:	1.7179805581690744e-05
Pgp-inhibitor:	0.98
Pgp-substrate:	0.84
Human Intestinal Absorption (HIA):	0.052
20% Bioavailability (F20%):	0.02
30% Bioavailability (F30%):	0.707

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.842
Plasma Protein Binding (PPB):	80.69564056396484%
Volume Distribution (VD):	0.666
Pgp-substrate:	12.733352661132812%

ADMET: Metabolism

CYP1A2-inhibitor:	0.02
CYP1A2-substrate:	0.846
CYP2C19-inhibitor:	0.069
CYP2C19-substrate:	0.785
CYP2C9-inhibitor:	0.062
CYP2C9-substrate:	0.015
CYP2D6-inhibitor:	0.005
CYP2D6-substrate:	0.18
CYP3A4-inhibitor:	0.748
CYP3A4-substrate:	0.322

ADMET: Excretion

Clearance (CL):	16.394
Half-life (T1/2):	0.207

ADMET: Toxicity

hERG Blockers:	0.222
Human Hepatotoxicity (H-HT):	0.477
Drug-inuced Liver Injury (DILI):	0.208
AMES Toxicity:	0.011
Rat Oral Acute Toxicity:	0.676
Maximum Recommended Daily Dose:	0.937
Skin Sensitization:	0.314
Carcinogencity:	0.405
Eye Corrosion:	0.016
Eye Irritation:	0.017
Respiratory Toxicity:	0.985

Download Data

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

Natural Product: NPC163314

Natural Product ID:	NPC163314
*Common Name:**	Muzanzagenin
IUPAC Name:	n.a.
Synonyms:	Muzanzagenin
Standard InCHIKey:	QRAOBCVRMVGMTN-QWNORFRRSA-N
Standard InCHI:	InChI=1S/C27H38O5/c1-14-7-8-27(31-13-14)15(2)24-22(32-27)10-19-17-6-5-16-9-20(28)21(29)12-25(16,3)18(17)11-23(30)26(19,24)4/h6,9,14-15,18-19,21-24,29-30H,5,7-8,10-13H2,1-4H3/t14-,15+,18+,19+,21+,22+,23+,24+,25+,26-,27-/m1/s1
SMILES:	C[C@@H]1CC[C@@]2([C@@H](C)[C@H]3[C@H](C[C@H]4C5=CCC6=CC(=O)[C@H](C[C@]6(C)[C@H]5C[C@@H]([C@]34C)O)O)O2)OC1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL455616
PubChem CID:	10836928
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001194] Oxosteroids

*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
NPO15006	Asparagus africanus	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9358645]
NPO15006	Asparagus africanus	Species	Asparagaceae	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	6
Others	5

Activity Type	# Activity
Organism	5
Others	6

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT841	Organism	Leishmania major	Leishmania major	IC50	=	70000.0	nM	PMID[447458]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	61000.0	nM	PMID[447458]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	163000.0	nM	PMID[447458]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	23000.0	nM	PMID[447458]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	16000.0	nM	PMID[447458]
NPT27	Others	Unspecified		IC50	=	129000.0	nM	PMID[447458]
NPT2	Others	Unspecified		Ratio IC50	=	1.8	n.a.	PMID[447458]
NPT2	Others	Unspecified		Ratio IC50	=	2.1	n.a.	PMID[447458]
NPT2	Others	Unspecified		Ratio IC50	=	0.8	n.a.	PMID[447458]
NPT2	Others	Unspecified		Ratio IC50	=	5.6	n.a.	PMID[447458]
NPT2	Others	Unspecified		Ratio IC50	=	8.0	n.a.	PMID[447458]

☑ 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 NPC163314 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	224
0.1-0.2	1400
0.2-0.3	5108
0.3-0.4	11208
0.4-0.5	10214
0.5-0.6	6094
0.6-0.7	6213
0.7-0.8	2157
0.8-0.85	72
0.85-0.9	6
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8981	High Similarity	NPC178981
0.8725	High Similarity	NPC187159
0.8679	High Similarity	NPC470309
0.8636	High Similarity	NPC260665
0.8559	High Similarity	NPC477580
0.8532	High Similarity	NPC197428
0.8519	High Similarity	NPC94529
0.8468	Intermediate Similarity	NPC194100
0.8431	Intermediate Similarity	NPC245972
0.8431	Intermediate Similarity	NPC111015
0.8431	Intermediate Similarity	NPC196485
0.8396	Intermediate Similarity	NPC22388
0.8393	Intermediate Similarity	NPC471398
0.8381	Intermediate Similarity	NPC15390
0.8378	Intermediate Similarity	NPC130427
0.8365	Intermediate Similarity	NPC177818
0.8348	Intermediate Similarity	NPC471406
0.8333	Intermediate Similarity	NPC242419
0.8333	Intermediate Similarity	NPC278628
0.8333	Intermediate Similarity	NPC231530
0.8333	Intermediate Similarity	NPC235126
0.8318	Intermediate Similarity	NPC140723
0.8305	Intermediate Similarity	NPC47113
0.8305	Intermediate Similarity	NPC174367
0.8304	Intermediate Similarity	NPC477944
0.8302	Intermediate Similarity	NPC474022
0.8288	Intermediate Similarity	NPC201992
0.8276	Intermediate Similarity	NPC476545
0.8276	Intermediate Similarity	NPC476544
0.8276	Intermediate Similarity	NPC476543
0.8273	Intermediate Similarity	NPC246205
0.8241	Intermediate Similarity	NPC472228
0.8241	Intermediate Similarity	NPC472227
0.823	Intermediate Similarity	NPC474906
0.823	Intermediate Similarity	NPC474557
0.823	Intermediate Similarity	NPC74727
0.823	Intermediate Similarity	NPC18547
0.822	Intermediate Similarity	NPC475194
0.822	Intermediate Similarity	NPC277191
0.822	Intermediate Similarity	NPC190846
0.8214	Intermediate Similarity	NPC11252
0.8214	Intermediate Similarity	NPC289312
0.8214	Intermediate Similarity	NPC71348
0.8208	Intermediate Similarity	NPC327431
0.8208	Intermediate Similarity	NPC83709
0.8205	Intermediate Similarity	NPC313528
0.8198	Intermediate Similarity	NPC475317
0.8198	Intermediate Similarity	NPC154856
0.8198	Intermediate Similarity	NPC52241
0.8198	Intermediate Similarity	NPC129340
0.819	Intermediate Similarity	NPC190554
0.8167	Intermediate Similarity	NPC69273
0.8167	Intermediate Similarity	NPC168899
0.8167	Intermediate Similarity	NPC293623
0.8158	Intermediate Similarity	NPC134869
0.8158	Intermediate Similarity	NPC235539
0.8158	Intermediate Similarity	NPC270958
0.8158	Intermediate Similarity	NPC152199
0.8151	Intermediate Similarity	NPC93368
0.8148	Intermediate Similarity	NPC475701
0.8142	Intermediate Similarity	NPC202889
0.8142	Intermediate Similarity	NPC51978
0.8142	Intermediate Similarity	NPC52634
0.8142	Intermediate Similarity	NPC251309
0.8131	Intermediate Similarity	NPC176406
0.8125	Intermediate Similarity	NPC207689
0.812	Intermediate Similarity	NPC42675
0.812	Intermediate Similarity	NPC202051
0.8119	Intermediate Similarity	NPC471722
0.8113	Intermediate Similarity	NPC275865
0.8108	Intermediate Similarity	NPC265655
0.8108	Intermediate Similarity	NPC470615
0.8103	Intermediate Similarity	NPC161738
0.8099	Intermediate Similarity	NPC471407
0.8095	Intermediate Similarity	NPC305483
0.8095	Intermediate Similarity	NPC96859
0.8095	Intermediate Similarity	NPC173272
0.8095	Intermediate Similarity	NPC328162
0.8073	Intermediate Similarity	NPC222161
0.8073	Intermediate Similarity	NPC121566
0.8073	Intermediate Similarity	NPC100955
0.8073	Intermediate Similarity	NPC96268
0.8073	Intermediate Similarity	NPC137657
0.8073	Intermediate Similarity	NPC474464
0.8073	Intermediate Similarity	NPC29705
0.8067	Intermediate Similarity	NPC473505
0.8056	Intermediate Similarity	NPC22634
0.8053	Intermediate Similarity	NPC210420
0.8053	Intermediate Similarity	NPC474265
0.8053	Intermediate Similarity	NPC233003
0.8051	Intermediate Similarity	NPC216866
0.8051	Intermediate Similarity	NPC28532
0.8051	Intermediate Similarity	NPC131824
0.8051	Intermediate Similarity	NPC475431
0.8051	Intermediate Similarity	NPC222688
0.8037	Intermediate Similarity	NPC472972
0.8037	Intermediate Similarity	NPC154072
0.8036	Intermediate Similarity	NPC27551
0.8036	Intermediate Similarity	NPC272898
0.8036	Intermediate Similarity	NPC101450
0.8036	Intermediate Similarity	NPC473036
0.8036	Intermediate Similarity	NPC114961
0.8034	Intermediate Similarity	NPC109973
0.8033	Intermediate Similarity	NPC241008
0.8019	Intermediate Similarity	NPC18509
0.8019	Intermediate Similarity	NPC320306
0.8019	Intermediate Similarity	NPC108078
0.8018	Intermediate Similarity	NPC258323
0.8018	Intermediate Similarity	NPC295389
0.8018	Intermediate Similarity	NPC272576
0.8018	Intermediate Similarity	NPC195708
0.8017	Intermediate Similarity	NPC473888
0.8017	Intermediate Similarity	NPC297179
0.8017	Intermediate Similarity	NPC118638
0.8017	Intermediate Similarity	NPC311534
0.8	Intermediate Similarity	NPC257353
0.8	Intermediate Similarity	NPC266728
0.8	Intermediate Similarity	NPC63023
0.8	Intermediate Similarity	NPC317586
0.8	Intermediate Similarity	NPC49492
0.8	Intermediate Similarity	NPC302471
0.8	Intermediate Similarity	NPC210178
0.8	Intermediate Similarity	NPC31797
0.8	Intermediate Similarity	NPC95243
0.8	Intermediate Similarity	NPC69548
0.8	Intermediate Similarity	NPC162033
0.8	Intermediate Similarity	NPC475571
0.8	Intermediate Similarity	NPC184848
0.8	Intermediate Similarity	NPC48330
0.8	Intermediate Similarity	NPC470016
0.8	Intermediate Similarity	NPC305808
0.8	Intermediate Similarity	NPC474015
0.7983	Intermediate Similarity	NPC141196
0.7983	Intermediate Similarity	NPC228701
0.7983	Intermediate Similarity	NPC476542
0.7983	Intermediate Similarity	NPC238005
0.7983	Intermediate Similarity	NPC1980
0.7982	Intermediate Similarity	NPC471627
0.7982	Intermediate Similarity	NPC159442
0.7982	Intermediate Similarity	NPC275583
0.7982	Intermediate Similarity	NPC200944
0.7982	Intermediate Similarity	NPC471173
0.7982	Intermediate Similarity	NPC472926
0.7982	Intermediate Similarity	NPC73455
0.7967	Intermediate Similarity	NPC471855
0.7966	Intermediate Similarity	NPC249553
0.7966	Intermediate Similarity	NPC470921
0.7966	Intermediate Similarity	NPC182900
0.7965	Intermediate Similarity	NPC250481
0.7965	Intermediate Similarity	NPC231589
0.7965	Intermediate Similarity	NPC471243
0.7965	Intermediate Similarity	NPC292196
0.7965	Intermediate Similarity	NPC285410
0.7965	Intermediate Similarity	NPC214797
0.7965	Intermediate Similarity	NPC263827
0.7965	Intermediate Similarity	NPC118860
0.7965	Intermediate Similarity	NPC269466
0.7965	Intermediate Similarity	NPC470311
0.7961	Intermediate Similarity	NPC219495
0.7949	Intermediate Similarity	NPC475775
0.7949	Intermediate Similarity	NPC319570
0.7949	Intermediate Similarity	NPC476529
0.7949	Intermediate Similarity	NPC19028
0.7949	Intermediate Similarity	NPC475834
0.7949	Intermediate Similarity	NPC9674
0.7949	Intermediate Similarity	NPC474179
0.7946	Intermediate Similarity	NPC258543
0.7946	Intermediate Similarity	NPC477069
0.7946	Intermediate Similarity	NPC241927
0.7946	Intermediate Similarity	NPC304495
0.7946	Intermediate Similarity	NPC477070
0.7944	Intermediate Similarity	NPC477813
0.7934	Intermediate Similarity	NPC305496
0.7934	Intermediate Similarity	NPC152091
0.7931	Intermediate Similarity	NPC218970
0.7931	Intermediate Similarity	NPC309433
0.7928	Intermediate Similarity	NPC144854
0.7928	Intermediate Similarity	NPC472925
0.7928	Intermediate Similarity	NPC44063
0.7928	Intermediate Similarity	NPC293512
0.7928	Intermediate Similarity	NPC3316
0.7925	Intermediate Similarity	NPC42042
0.7925	Intermediate Similarity	NPC253115
0.7925	Intermediate Similarity	NPC7124
0.7925	Intermediate Similarity	NPC304899
0.7921	Intermediate Similarity	NPC72133
0.7917	Intermediate Similarity	NPC473255
0.7913	Intermediate Similarity	NPC326542
0.7913	Intermediate Similarity	NPC473882
0.7913	Intermediate Similarity	NPC243354
0.7913	Intermediate Similarity	NPC473798
0.7913	Intermediate Similarity	NPC165439
0.7909	Intermediate Similarity	NPC471111
0.7909	Intermediate Similarity	NPC235889
0.7909	Intermediate Similarity	NPC28656
0.7909	Intermediate Similarity	NPC223741
0.7905	Intermediate Similarity	NPC166906
0.7899	Intermediate Similarity	NPC94072
0.7899	Intermediate Similarity	NPC305771
0.7899	Intermediate Similarity	NPC169816

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 NPC163314 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	193
0.1-0.2	1615
0.2-0.3	4106
0.3-0.4	2203
0.4-0.5	555
0.5-0.6	169
0.6-0.7	146
0.7-0.8	141
0.8-0.85	20
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8509	High Similarity	NPD6054	Approved
0.8509	High Similarity	NPD6059	Approved
0.8426	Intermediate Similarity	NPD6412	Phase 2
0.8362	Intermediate Similarity	NPD6370	Approved
0.8276	Intermediate Similarity	NPD6016	Approved
0.8276	Intermediate Similarity	NPD6015	Approved
0.822	Intermediate Similarity	NPD7492	Approved
0.8214	Intermediate Similarity	NPD6882	Approved
0.8205	Intermediate Similarity	NPD5988	Approved
0.8182	Intermediate Similarity	NPD7320	Approved
0.8167	Intermediate Similarity	NPD7736	Approved
0.8165	Intermediate Similarity	NPD7128	Approved
0.8165	Intermediate Similarity	NPD6402	Approved
0.8165	Intermediate Similarity	NPD5739	Approved
0.8165	Intermediate Similarity	NPD6675	Approved
0.8151	Intermediate Similarity	NPD6616	Approved
0.8087	Intermediate Similarity	NPD6009	Approved
0.8083	Intermediate Similarity	NPD8293	Discontinued
0.8083	Intermediate Similarity	NPD7078	Approved
0.8019	Intermediate Similarity	NPD4755	Approved
0.8018	Intermediate Similarity	NPD6881	Approved
0.8018	Intermediate Similarity	NPD6899	Approved
0.8017	Intermediate Similarity	NPD6033	Approved
0.8	Intermediate Similarity	NPD6008	Approved
0.7946	Intermediate Similarity	NPD6373	Approved
0.7946	Intermediate Similarity	NPD6372	Approved
0.7928	Intermediate Similarity	NPD5701	Approved
0.7928	Intermediate Similarity	NPD5697	Approved
0.7876	Intermediate Similarity	NPD6883	Approved
0.7876	Intermediate Similarity	NPD7102	Approved
0.7876	Intermediate Similarity	NPD7290	Approved
0.787	Intermediate Similarity	NPD4696	Approved
0.787	Intermediate Similarity	NPD5285	Approved
0.787	Intermediate Similarity	NPD4700	Approved
0.787	Intermediate Similarity	NPD5286	Approved
0.7857	Intermediate Similarity	NPD6011	Approved
0.785	Intermediate Similarity	NPD6084	Phase 2
0.785	Intermediate Similarity	NPD6083	Phase 2
0.7833	Intermediate Similarity	NPD6067	Discontinued
0.783	Intermediate Similarity	NPD5695	Phase 3
0.7826	Intermediate Similarity	NPD4632	Approved
0.781	Intermediate Similarity	NPD4202	Approved
0.7807	Intermediate Similarity	NPD6847	Approved
0.7807	Intermediate Similarity	NPD8130	Phase 1
0.7807	Intermediate Similarity	NPD6650	Approved
0.7807	Intermediate Similarity	NPD6617	Approved
0.7807	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7807	Intermediate Similarity	NPD6869	Approved
0.7807	Intermediate Similarity	NPD6649	Approved
0.7798	Intermediate Similarity	NPD5223	Approved
0.7788	Intermediate Similarity	NPD6013	Approved
0.7788	Intermediate Similarity	NPD6014	Approved
0.7788	Intermediate Similarity	NPD6012	Approved
0.7739	Intermediate Similarity	NPD8297	Approved
0.7727	Intermediate Similarity	NPD5224	Approved
0.7727	Intermediate Similarity	NPD5211	Phase 2
0.7727	Intermediate Similarity	NPD4633	Approved
0.7727	Intermediate Similarity	NPD5226	Approved
0.7727	Intermediate Similarity	NPD5225	Approved
0.7705	Intermediate Similarity	NPD7507	Approved
0.7692	Intermediate Similarity	NPD5328	Approved
0.7692	Intermediate Similarity	NPD4753	Phase 2
0.7658	Intermediate Similarity	NPD5174	Approved
0.7658	Intermediate Similarity	NPD5175	Approved
0.7658	Intermediate Similarity	NPD4754	Approved
0.7642	Intermediate Similarity	NPD6399	Phase 3
0.7615	Intermediate Similarity	NPD7638	Approved
0.7593	Intermediate Similarity	NPD5222	Approved
0.7593	Intermediate Similarity	NPD5221	Approved
0.7593	Intermediate Similarity	NPD4697	Phase 3
0.7593	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7589	Intermediate Similarity	NPD5141	Approved
0.7583	Intermediate Similarity	NPD6319	Approved
0.7573	Intermediate Similarity	NPD5279	Phase 3
0.7573	Intermediate Similarity	NPD3618	Phase 1
0.7565	Intermediate Similarity	NPD4634	Approved
0.7549	Intermediate Similarity	NPD3133	Approved
0.7549	Intermediate Similarity	NPD3666	Approved
0.7549	Intermediate Similarity	NPD3665	Phase 1
0.7549	Intermediate Similarity	NPD4786	Approved
0.7547	Intermediate Similarity	NPD6079	Approved
0.7545	Intermediate Similarity	NPD7640	Approved
0.7545	Intermediate Similarity	NPD7639	Approved
0.7541	Intermediate Similarity	NPD7604	Phase 2
0.7523	Intermediate Similarity	NPD5173	Approved
0.7522	Intermediate Similarity	NPD4767	Approved
0.7522	Intermediate Similarity	NPD4768	Approved
0.7521	Intermediate Similarity	NPD5983	Phase 2
0.752	Intermediate Similarity	NPD7319	Approved
0.75	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7476	Intermediate Similarity	NPD5329	Approved
0.7455	Intermediate Similarity	NPD5696	Approved
0.7429	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7429	Intermediate Similarity	NPD6903	Approved
0.7429	Intermediate Similarity	NPD5737	Approved
0.7429	Intermediate Similarity	NPD6672	Approved
0.7419	Intermediate Similarity	NPD6336	Discontinued
0.7417	Intermediate Similarity	NPD7328	Approved
0.7417	Intermediate Similarity	NPD7327	Approved
0.7417	Intermediate Similarity	NPD6335	Approved
0.7407	Intermediate Similarity	NPD7748	Approved
0.7404	Intermediate Similarity	NPD4694	Approved
0.7404	Intermediate Similarity	NPD7334	Approved
0.7404	Intermediate Similarity	NPD7146	Approved
0.7404	Intermediate Similarity	NPD7521	Approved
0.7404	Intermediate Similarity	NPD5330	Approved
0.7404	Intermediate Similarity	NPD6409	Approved
0.7404	Intermediate Similarity	NPD5690	Phase 2
0.7404	Intermediate Similarity	NPD5280	Approved
0.7404	Intermediate Similarity	NPD6684	Approved
0.7398	Intermediate Similarity	NPD8328	Phase 3
0.7395	Intermediate Similarity	NPD6274	Approved
0.7391	Intermediate Similarity	NPD4729	Approved
0.7391	Intermediate Similarity	NPD5128	Approved
0.7391	Intermediate Similarity	NPD4730	Approved
0.7383	Intermediate Similarity	NPD7515	Phase 2
0.7383	Intermediate Similarity	NPD6050	Approved
0.7379	Intermediate Similarity	NPD4197	Approved
0.7377	Intermediate Similarity	NPD8033	Approved
0.7377	Intermediate Similarity	NPD6291	Clinical (unspecified phase)
0.7364	Intermediate Similarity	NPD7902	Approved
0.7358	Intermediate Similarity	NPD6080	Approved
0.7358	Intermediate Similarity	NPD6904	Approved
0.7358	Intermediate Similarity	NPD6673	Approved
0.7355	Intermediate Similarity	NPD7101	Approved
0.7355	Intermediate Similarity	NPD7100	Approved
0.7355	Intermediate Similarity	NPD7516	Approved
0.7353	Intermediate Similarity	NPD3667	Approved
0.7339	Intermediate Similarity	NPD5210	Approved
0.7339	Intermediate Similarity	NPD4629	Approved
0.7333	Intermediate Similarity	NPD6317	Approved
0.7328	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7323	Intermediate Similarity	NPD5956	Approved
0.7295	Intermediate Similarity	NPD8294	Approved
0.7295	Intermediate Similarity	NPD8377	Approved
0.729	Intermediate Similarity	NPD5692	Phase 3
0.7273	Intermediate Similarity	NPD6314	Approved
0.7273	Intermediate Similarity	NPD6313	Approved
0.7265	Intermediate Similarity	NPD5250	Approved
0.7265	Intermediate Similarity	NPD5248	Approved
0.7265	Intermediate Similarity	NPD5169	Approved
0.7265	Intermediate Similarity	NPD5251	Approved
0.7265	Intermediate Similarity	NPD5247	Approved
0.7265	Intermediate Similarity	NPD5249	Phase 3
0.7265	Intermediate Similarity	NPD5134	Clinical (unspecified phase)
0.7265	Intermediate Similarity	NPD5135	Approved
0.7236	Intermediate Similarity	NPD8335	Approved
0.7236	Intermediate Similarity	NPD6908	Approved
0.7236	Intermediate Similarity	NPD8378	Approved
0.7236	Intermediate Similarity	NPD8379	Approved
0.7236	Intermediate Similarity	NPD6909	Approved
0.7236	Intermediate Similarity	NPD8380	Approved
0.7236	Intermediate Similarity	NPD8296	Approved
0.7222	Intermediate Similarity	NPD5281	Approved
0.7222	Intermediate Similarity	NPD5284	Approved
0.7222	Intermediate Similarity	NPD5694	Approved
0.7203	Intermediate Similarity	NPD5217	Approved
0.7203	Intermediate Similarity	NPD5216	Approved
0.7203	Intermediate Similarity	NPD5215	Approved
0.7203	Intermediate Similarity	NPD5127	Approved
0.7184	Intermediate Similarity	NPD4223	Phase 3
0.7184	Intermediate Similarity	NPD4221	Approved
0.7143	Intermediate Similarity	NPD6053	Discontinued
0.713	Intermediate Similarity	NPD5207	Approved
0.7107	Intermediate Similarity	NPD6868	Approved
0.7097	Intermediate Similarity	NPD7503	Approved
0.7094	Intermediate Similarity	NPD6686	Approved
0.7091	Intermediate Similarity	NPD5282	Discontinued
0.7091	Intermediate Similarity	NPD6001	Approved
0.7091	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD7900	Approved
0.7075	Intermediate Similarity	NPD6098	Approved
0.7064	Intermediate Similarity	NPD8034	Phase 2
0.7064	Intermediate Similarity	NPD8035	Phase 2
0.7064	Intermediate Similarity	NPD5693	Phase 1
0.7049	Intermediate Similarity	NPD7115	Discovery
0.7049	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD5167	Approved
0.699	Remote Similarity	NPD6928	Phase 2
0.6983	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD7632	Discontinued
0.6949	Remote Similarity	NPD5168	Approved
0.6942	Remote Similarity	NPD8133	Approved
0.6916	Remote Similarity	NPD4690	Approved
0.6916	Remote Similarity	NPD4693	Phase 3
0.6916	Remote Similarity	NPD4138	Approved
0.6916	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6916	Remote Similarity	NPD5205	Approved
0.6916	Remote Similarity	NPD4689	Approved
0.6916	Remote Similarity	NPD4688	Approved
0.6887	Remote Similarity	NPD3668	Phase 3
0.6881	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD5654	Approved
0.6847	Remote Similarity	NPD5133	Approved
0.6827	Remote Similarity	NPD4695	Discontinued
0.6827	Remote Similarity	NPD7525	Registered
0.6815	Remote Similarity	NPD6334	Approved
0.6815	Remote Similarity	NPD6333	Approved
0.6796	Remote Similarity	NPD3617	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