NPASS Compound

Structure

NPC470656 OpenBabel07101719252D 34 38 0 0 1 0 0 0 0 0999 V2000 -0.8438 -2.4359 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -3.8974 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1822 2.4146 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2555 2.7157 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1352 -0.4029 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.9744 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8438 -1.4615 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6876 -0.9744 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6876 1.9487 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8438 1.4615 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0308 0.9744 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4581 0.1861 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6876 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8438 0.4872 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8438 -2.4359 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7895 -1.9434 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -2.9231 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.9744 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8438 -1.4615 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5315 1.4615 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6876 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.7426 -2.1460 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 0.0000 1.9487 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5778 -0.5781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4581 1.7626 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5315 0.4872 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8438 0.4872 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6876 -0.9744 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 3.1389 -3.0361 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8438 2.4359 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8438 2.4359 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.7803 0.3750 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.2297 -1.3021 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 17 1 0 0 0 0 2 17 1 0 0 0 0 3 25 1 0 0 0 0 4 25 1 0 0 0 0 6 27 1 0 0 0 0 7 8 1 0 0 0 0 7 18 1 0 0 0 0 8 21 1 0 0 0 0 9 10 1 0 0 0 0 9 20 1 0 0 0 0 10 27 1 0 0 0 0 11 12 2 0 0 0 0 11 25 1 0 0 0 0 12 26 1 0 0 0 0 13 14 1 0 0 0 0 14 29 1 0 0 0 0 15 17 2 0 0 0 0 15 19 1 0 0 0 0 16 22 1 0 0 0 0 16 28 1 0 0 0 0 18 19 1 0 0 0 0 18 29 1 1 0 0 0 19 28 1 6 0 0 0 20 25 1 0 0 0 0 20 26 1 6 0 0 0 21 26 1 6 0 0 0 21 27 1 0 0 0 0 22 30 1 0 0 0 0 22 34 1 0 0 0 0 23 31 2 0 0 0 0 23 32 1 0 0 0 0 24 28 1 0 0 0 0 24 33 2 0 0 0 0 24 34 1 0 0 0 0 26 5 1 6 0 0 0 27 29 1 1 0 0 0 28 13 1 1 0 0 0 29 23 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	470.3
Volume:	500.763
LogP:	5.302
LogD:	4.353
LogS:	-4.636
# Rotatable Bonds:	2
TPSA:	83.83
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	5
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.398
Synthetic Accessibility Score:	5.846
Fsp3:	0.793
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:	-5.527
MDCK Permeability:	1.3433880667435005e-05
Pgp-inhibitor:	0.011
Pgp-substrate:	0.478
Human Intestinal Absorption (HIA):	0.01
20% Bioavailability (F20%):	0.122
30% Bioavailability (F30%):	0.853

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.125
Plasma Protein Binding (PPB):	88.33712005615234%
Volume Distribution (VD):	0.569
Pgp-substrate:	3.8500900268554688%

ADMET: Metabolism

CYP1A2-inhibitor:	0.014
CYP1A2-substrate:	0.244
CYP2C19-inhibitor:	0.027
CYP2C19-substrate:	0.788
CYP2C9-inhibitor:	0.147
CYP2C9-substrate:	0.477
CYP2D6-inhibitor:	0.006
CYP2D6-substrate:	0.11
CYP3A4-inhibitor:	0.411
CYP3A4-substrate:	0.276

ADMET: Excretion

Clearance (CL):	2.346
Half-life (T1/2):	0.084

ADMET: Toxicity

hERG Blockers:	0.031
Human Hepatotoxicity (H-HT):	0.535
Drug-inuced Liver Injury (DILI):	0.024
AMES Toxicity:	0.012
Rat Oral Acute Toxicity:	0.655
Maximum Recommended Daily Dose:	0.53
Skin Sensitization:	0.107
Carcinogencity:	0.278
Eye Corrosion:	0.009
Eye Irritation:	0.027
Respiratory Toxicity:	0.951

Download Data

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

Natural Product: NPC470656

Natural Product ID:	NPC470656
*Common Name:**	Zizimauritic Acid C
IUPAC Name:	(3R,4R,5R,8R,9R,10S,13S,14S)-5'-hydroxy-9,14,17,17-tetramethyl-4-(2-methylprop-1-enyl)-2'-oxospiro[1,2,4,5,6,7,8,11,12,13-decahydrocyclopenta[a]phenanthrene-3,3'-oxolane]-10-carboxylic acid
Synonyms:	Zizimauritic Acid C
Standard InCHIKey:	HSWHHIVUFILTFY-NKMSWGSJSA-N
Standard InCHI:	InChI=1S/C29H42O5/c1-17(2)15-19-18-7-8-21-26(5)12-11-25(3,4)20(26)9-10-27(21,6)29(18,23(31)32)14-13-28(19)16-22(30)34-24(28)33/h11-12,15,18-22,30H,7-10,13-14,16H2,1-6H3,(H,31,32)/t18-,19-,20+,21-,22?,26+,27-,28-,29-/m1/s1
SMILES:	CC(=CC1C2CCC3C(C2(CCC14CC(OC4=O)O)C(=O)O)(CCC5C3(C=CC5(C)C)C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2151977
PubChem CID:	71460246
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001125] Steroid lactones

*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
NPO4792	Ziziphus mauritiana	Species	Rhamnaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22989532]
NPO4792	Ziziphus mauritiana	Species	Rhamnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO4792	Ziziphus mauritiana	Species	Rhamnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4792	Ziziphus mauritiana	Species	Rhamnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]

☑ 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	3
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	IC50	=	11.94	ug.mL-1	PMID[513637]
NPT547	Cell Line	BGC-823	Homo sapiens	IC50	=	10.06	ug.mL-1	PMID[513637]
NPT165	Cell Line	HeLa	Homo sapiens	IC50	=	9.25	ug.mL-1	PMID[513637]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	IC50	=	12.79	ug.mL-1	PMID[513637]
NPT20	Organism	Candida albicans	Candida albicans	IC50	>	10.0	ug.mL-1	PMID[513637]

☑ 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 NPC470656 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	176
0.1-0.2	1071
0.2-0.3	5160
0.3-0.4	14654
0.4-0.5	7592
0.5-0.6	6129
0.6-0.7	5757
0.7-0.8	2127
0.8-0.85	25
0.85-0.9	3
0.9-0.95	0
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.977	High Similarity	NPC267266
0.977	High Similarity	NPC277721
0.8646	High Similarity	NPC63249
0.8557	High Similarity	NPC134077
0.8351	Intermediate Similarity	NPC477720
0.8333	Intermediate Similarity	NPC329738
0.8333	Intermediate Similarity	NPC76266
0.8317	Intermediate Similarity	NPC469844
0.8315	Intermediate Similarity	NPC167103
0.8191	Intermediate Similarity	NPC179517
0.8191	Intermediate Similarity	NPC165904
0.8182	Intermediate Similarity	NPC104545
0.8152	Intermediate Similarity	NPC167877
0.8144	Intermediate Similarity	NPC204054
0.8144	Intermediate Similarity	NPC257726
0.814	Intermediate Similarity	NPC476601
0.8137	Intermediate Similarity	NPC469845
0.8111	Intermediate Similarity	NPC215893
0.8105	Intermediate Similarity	NPC474436
0.8105	Intermediate Similarity	NPC49776
0.8105	Intermediate Similarity	NPC63118
0.8105	Intermediate Similarity	NPC166346
0.8105	Intermediate Similarity	NPC470224
0.8085	Intermediate Similarity	NPC477782
0.8068	Intermediate Similarity	NPC327674
0.8061	Intermediate Similarity	NPC164349
0.8043	Intermediate Similarity	NPC324063
0.8023	Intermediate Similarity	NPC201027
0.802	Intermediate Similarity	NPC472228
0.802	Intermediate Similarity	NPC472227
0.8	Intermediate Similarity	NPC477783
0.8	Intermediate Similarity	NPC154101
0.7978	Intermediate Similarity	NPC477057
0.7959	Intermediate Similarity	NPC475894
0.7955	Intermediate Similarity	NPC260385
0.7955	Intermediate Similarity	NPC280654
0.7955	Intermediate Similarity	NPC110094
0.7938	Intermediate Similarity	NPC275310
0.7938	Intermediate Similarity	NPC286612
0.7938	Intermediate Similarity	NPC139459
0.7938	Intermediate Similarity	NPC230347
0.7935	Intermediate Similarity	NPC76333
0.7935	Intermediate Similarity	NPC470223
0.7917	Intermediate Similarity	NPC141497
0.7917	Intermediate Similarity	NPC107674
0.7917	Intermediate Similarity	NPC170220
0.7912	Intermediate Similarity	NPC200752
0.7895	Intermediate Similarity	NPC193750
0.7895	Intermediate Similarity	NPC290614
0.7895	Intermediate Similarity	NPC471371
0.7895	Intermediate Similarity	NPC227467
0.7895	Intermediate Similarity	NPC273621
0.7895	Intermediate Similarity	NPC210037
0.7895	Intermediate Similarity	NPC471370
0.7895	Intermediate Similarity	NPC477872
0.7895	Intermediate Similarity	NPC120968
0.7895	Intermediate Similarity	NPC18872
0.7895	Intermediate Similarity	NPC7260
0.7889	Intermediate Similarity	NPC327002
0.7889	Intermediate Similarity	NPC14203
0.7889	Intermediate Similarity	NPC229584
0.7865	Intermediate Similarity	NPC199595
0.7864	Intermediate Similarity	NPC293512
0.7857	Intermediate Similarity	NPC235053
0.7857	Intermediate Similarity	NPC327179
0.7857	Intermediate Similarity	NPC471039
0.7857	Intermediate Similarity	NPC470801
0.7849	Intermediate Similarity	NPC6979
0.7849	Intermediate Similarity	NPC73038
0.7849	Intermediate Similarity	NPC244174
0.7849	Intermediate Similarity	NPC325594
0.7843	Intermediate Similarity	NPC222161
0.7843	Intermediate Similarity	NPC100955
0.7843	Intermediate Similarity	NPC121566
0.7841	Intermediate Similarity	NPC471899
0.7841	Intermediate Similarity	NPC107039
0.7841	Intermediate Similarity	NPC471897
0.7835	Intermediate Similarity	NPC474963
0.7835	Intermediate Similarity	NPC159410
0.783	Intermediate Similarity	NPC194951
0.783	Intermediate Similarity	NPC12046
0.7826	Intermediate Similarity	NPC100391
0.7826	Intermediate Similarity	NPC156981
0.7816	Intermediate Similarity	NPC279666
0.7816	Intermediate Similarity	NPC192540
0.7812	Intermediate Similarity	NPC65513
0.7812	Intermediate Similarity	NPC38754
0.7812	Intermediate Similarity	NPC212301
0.7812	Intermediate Similarity	NPC86266
0.7812	Intermediate Similarity	NPC105189
0.7812	Intermediate Similarity	NPC187722
0.7812	Intermediate Similarity	NPC110657
0.781	Intermediate Similarity	NPC101450
0.7802	Intermediate Similarity	NPC15910
0.7789	Intermediate Similarity	NPC477973
0.7789	Intermediate Similarity	NPC25906
0.7789	Intermediate Similarity	NPC64872
0.7789	Intermediate Similarity	NPC251528
0.7789	Intermediate Similarity	NPC474570
0.7789	Intermediate Similarity	NPC174342
0.7789	Intermediate Similarity	NPC474700
0.7789	Intermediate Similarity	NPC290972
0.7778	Intermediate Similarity	NPC107243
0.7778	Intermediate Similarity	NPC57416
0.7778	Intermediate Similarity	NPC37038
0.7767	Intermediate Similarity	NPC95243
0.7767	Intermediate Similarity	NPC63023
0.7766	Intermediate Similarity	NPC158141
0.7766	Intermediate Similarity	NPC173089
0.7766	Intermediate Similarity	NPC96496
0.7766	Intermediate Similarity	NPC477926
0.7757	Intermediate Similarity	NPC157441
0.7755	Intermediate Similarity	NPC469599
0.7755	Intermediate Similarity	NPC279974
0.7753	Intermediate Similarity	NPC321514
0.7753	Intermediate Similarity	NPC239098
0.7745	Intermediate Similarity	NPC140723
0.7742	Intermediate Similarity	NPC476602
0.7742	Intermediate Similarity	NPC283733
0.7732	Intermediate Similarity	NPC470376
0.7732	Intermediate Similarity	NPC158059
0.7732	Intermediate Similarity	NPC151722
0.7732	Intermediate Similarity	NPC118519
0.7732	Intermediate Similarity	NPC118490
0.7732	Intermediate Similarity	NPC229281
0.7732	Intermediate Similarity	NPC470375
0.7732	Intermediate Similarity	NPC202728
0.7732	Intermediate Similarity	NPC86368
0.7732	Intermediate Similarity	NPC472303
0.7727	Intermediate Similarity	NPC69143
0.7727	Intermediate Similarity	NPC41017
0.7727	Intermediate Similarity	NPC89294
0.7723	Intermediate Similarity	NPC235142
0.7717	Intermediate Similarity	NPC470948
0.7717	Intermediate Similarity	NPC312480
0.7717	Intermediate Similarity	NPC471037
0.7708	Intermediate Similarity	NPC120840
0.7708	Intermediate Similarity	NPC291028
0.7708	Intermediate Similarity	NPC113989
0.7708	Intermediate Similarity	NPC474728
0.7708	Intermediate Similarity	NPC130278
0.7708	Intermediate Similarity	NPC471896
0.7701	Intermediate Similarity	NPC283908
0.7701	Intermediate Similarity	NPC476046
0.7701	Intermediate Similarity	NPC241854
0.7701	Intermediate Similarity	NPC103958
0.7701	Intermediate Similarity	NPC251970
0.7701	Intermediate Similarity	NPC183503
0.7701	Intermediate Similarity	NPC166797
0.7701	Intermediate Similarity	NPC161923
0.77	Intermediate Similarity	NPC194196
0.77	Intermediate Similarity	NPC124703
0.77	Intermediate Similarity	NPC473154
0.77	Intermediate Similarity	NPC234617
0.77	Intermediate Similarity	NPC241657
0.7692	Intermediate Similarity	NPC223330
0.7692	Intermediate Similarity	NPC232625
0.7692	Intermediate Similarity	NPC473538
0.7692	Intermediate Similarity	NPC221647
0.7692	Intermediate Similarity	NPC209318
0.7692	Intermediate Similarity	NPC283849
0.7692	Intermediate Similarity	NPC474955
0.7684	Intermediate Similarity	NPC182797
0.7684	Intermediate Similarity	NPC474845
0.7684	Intermediate Similarity	NPC294480
0.7684	Intermediate Similarity	NPC28227
0.7684	Intermediate Similarity	NPC1753
0.7684	Intermediate Similarity	NPC52169
0.7684	Intermediate Similarity	NPC246708
0.7684	Intermediate Similarity	NPC474511
0.7684	Intermediate Similarity	NPC263079
0.7684	Intermediate Similarity	NPC40552
0.7677	Intermediate Similarity	NPC319692
0.7677	Intermediate Similarity	NPC322063
0.7677	Intermediate Similarity	NPC325960
0.767	Intermediate Similarity	NPC255309
0.7667	Intermediate Similarity	NPC16394
0.7667	Intermediate Similarity	NPC231431
0.766	Intermediate Similarity	NPC322159
0.766	Intermediate Similarity	NPC173917
0.766	Intermediate Similarity	NPC155011
0.7653	Intermediate Similarity	NPC324078
0.7653	Intermediate Similarity	NPC472223
0.7653	Intermediate Similarity	NPC49670
0.7653	Intermediate Similarity	NPC148964
0.7653	Intermediate Similarity	NPC114159
0.7653	Intermediate Similarity	NPC191412
0.7653	Intermediate Similarity	NPC60692
0.7653	Intermediate Similarity	NPC6818
0.7653	Intermediate Similarity	NPC471040
0.7653	Intermediate Similarity	NPC472224
0.7642	Intermediate Similarity	NPC127153
0.7642	Intermediate Similarity	NPC470065
0.764	Intermediate Similarity	NPC238227
0.7634	Intermediate Similarity	NPC194937
0.7634	Intermediate Similarity	NPC248758
0.7634	Intermediate Similarity	NPC476038
0.7629	Intermediate Similarity	NPC285184
0.7629	Intermediate Similarity	NPC470590
0.7629	Intermediate Similarity	NPC297265

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 NPC470656 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	145
0.1-0.2	1319
0.2-0.3	4029
0.3-0.4	2492
0.4-0.5	656
0.5-0.6	216
0.6-0.7	221
0.7-0.8	72
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
0.7917	Intermediate Similarity	NPD6399	Phase 3
0.76	Intermediate Similarity	NPD7902	Approved
0.7475	Intermediate Similarity	NPD7748	Approved
0.7453	Intermediate Similarity	NPD6686	Approved
0.7449	Intermediate Similarity	NPD7515	Phase 2
0.7449	Intermediate Similarity	NPD8034	Phase 2
0.7449	Intermediate Similarity	NPD8035	Phase 2
0.7426	Intermediate Similarity	NPD6083	Phase 2
0.7426	Intermediate Similarity	NPD6084	Phase 2
0.7358	Intermediate Similarity	NPD6412	Phase 2
0.732	Intermediate Similarity	NPD6672	Approved
0.732	Intermediate Similarity	NPD5737	Approved
0.732	Intermediate Similarity	NPD6903	Approved
0.732	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.73	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.73	Intermediate Similarity	NPD7900	Approved
0.7292	Intermediate Similarity	NPD6684	Approved
0.7292	Intermediate Similarity	NPD6409	Approved
0.7292	Intermediate Similarity	NPD5330	Approved
0.7292	Intermediate Similarity	NPD7521	Approved
0.7292	Intermediate Similarity	NPD7146	Approved
0.7292	Intermediate Similarity	NPD7334	Approved
0.7263	Intermediate Similarity	NPD4786	Approved
0.7234	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7234	Intermediate Similarity	NPD3667	Approved
0.7228	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7184	Intermediate Similarity	NPD5696	Approved
0.7184	Intermediate Similarity	NPD7638	Approved
0.7182	Intermediate Similarity	NPD6882	Approved
0.713	Intermediate Similarity	NPD7320	Approved
0.713	Intermediate Similarity	NPD6881	Approved
0.713	Intermediate Similarity	NPD6899	Approved
0.7115	Intermediate Similarity	NPD7640	Approved
0.7115	Intermediate Similarity	NPD7639	Approved
0.7113	Intermediate Similarity	NPD3618	Phase 1
0.7103	Intermediate Similarity	NPD7128	Approved
0.7103	Intermediate Similarity	NPD5739	Approved
0.7103	Intermediate Similarity	NPD6675	Approved
0.7103	Intermediate Similarity	NPD6402	Approved
0.71	Intermediate Similarity	NPD5281	Approved
0.71	Intermediate Similarity	NPD6411	Approved
0.71	Intermediate Similarity	NPD5284	Approved
0.7091	Intermediate Similarity	NPD6650	Approved
0.7091	Intermediate Similarity	NPD6649	Approved
0.7083	Intermediate Similarity	NPD3665	Phase 1
0.7083	Intermediate Similarity	NPD3666	Approved
0.7083	Intermediate Similarity	NPD3133	Approved
0.7064	Intermediate Similarity	NPD6373	Approved
0.7064	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7064	Intermediate Similarity	NPD6372	Approved
0.7059	Intermediate Similarity	NPD5695	Phase 3
0.7059	Intermediate Similarity	NPD7736	Approved
0.7037	Intermediate Similarity	NPD5697	Approved
0.7	Intermediate Similarity	NPD7102	Approved
0.7	Intermediate Similarity	NPD7290	Approved
0.7	Intermediate Similarity	NPD6883	Approved
0.7	Intermediate Similarity	NPD5207	Approved
0.6972	Remote Similarity	NPD6011	Approved
0.6939	Remote Similarity	NPD6098	Approved
0.6937	Remote Similarity	NPD6617	Approved
0.6937	Remote Similarity	NPD6869	Approved
0.6937	Remote Similarity	NPD6847	Approved
0.6937	Remote Similarity	NPD8130	Phase 1
0.6931	Remote Similarity	NPD6079	Approved
0.6923	Remote Similarity	NPD6370	Approved
0.6909	Remote Similarity	NPD6012	Approved
0.6909	Remote Similarity	NPD6013	Approved
0.6909	Remote Similarity	NPD6014	Approved
0.69	Remote Similarity	NPD6080	Approved
0.69	Remote Similarity	NPD6673	Approved
0.69	Remote Similarity	NPD5328	Approved
0.69	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.69	Remote Similarity	NPD4753	Phase 2
0.69	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.69	Remote Similarity	NPD6904	Approved
0.69	Remote Similarity	NPD6101	Approved
0.6893	Remote Similarity	NPD5210	Approved
0.6893	Remote Similarity	NPD4629	Approved
0.6893	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6891	Remote Similarity	NPD7507	Approved
0.6881	Remote Similarity	NPD5701	Approved
0.6875	Remote Similarity	NPD8297	Approved
0.6864	Remote Similarity	NPD8328	Phase 3
0.6842	Remote Similarity	NPD7525	Registered
0.6833	Remote Similarity	NPD8293	Discontinued
0.6814	Remote Similarity	NPD8133	Approved
0.6807	Remote Similarity	NPD7492	Approved
0.6804	Remote Similarity	NPD5362	Discontinued
0.6804	Remote Similarity	NPD4788	Approved
0.6796	Remote Similarity	NPD6001	Approved
0.6789	Remote Similarity	NPD6008	Approved
0.6786	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6783	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6768	Remote Similarity	NPD4623	Approved
0.6768	Remote Similarity	NPD4519	Discontinued
0.6752	Remote Similarity	NPD6054	Approved
0.675	Remote Similarity	NPD6616	Approved
0.6735	Remote Similarity	NPD3668	Phase 3
0.6723	Remote Similarity	NPD7122	Discontinued
0.6723	Remote Similarity	NPD6067	Discontinued
0.6721	Remote Similarity	NPD7319	Approved
0.6702	Remote Similarity	NPD6116	Phase 1
0.6701	Remote Similarity	NPD6435	Approved
0.6701	Remote Similarity	NPD4221	Approved
0.6701	Remote Similarity	NPD4223	Phase 3
0.67	Remote Similarity	NPD3573	Approved
0.6699	Remote Similarity	NPD4202	Approved
0.6698	Remote Similarity	NPD4225	Approved
0.6695	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6694	Remote Similarity	NPD7078	Approved
0.6667	Remote Similarity	NPD5349	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4695	Discontinued
0.6667	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5221	Approved
0.6667	Remote Similarity	NPD1694	Approved
0.6667	Remote Similarity	NPD4697	Phase 3
0.6667	Remote Similarity	NPD5329	Approved
0.6667	Remote Similarity	NPD5222	Approved
0.6638	Remote Similarity	NPD7115	Discovery
0.6638	Remote Similarity	NPD6009	Approved
0.6636	Remote Similarity	NPD4696	Approved
0.6636	Remote Similarity	NPD5285	Approved
0.6636	Remote Similarity	NPD5286	Approved
0.6635	Remote Similarity	NPD5282	Discontinued
0.6634	Remote Similarity	NPD5208	Approved
0.6633	Remote Similarity	NPD7154	Phase 3
0.6632	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.661	Remote Similarity	NPD6059	Approved
0.6606	Remote Similarity	NPD6052	Approved
0.6604	Remote Similarity	NPD4755	Approved
0.6604	Remote Similarity	NPD5173	Approved
0.6602	Remote Similarity	NPD5694	Approved
0.6602	Remote Similarity	NPD6050	Approved
0.6602	Remote Similarity	NPD7637	Suspended
0.6602	Remote Similarity	NPD5693	Phase 1
0.66	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.66	Remote Similarity	NPD5279	Phase 3
0.6598	Remote Similarity	NPD5369	Approved
0.6596	Remote Similarity	NPD6117	Approved
0.6581	Remote Similarity	NPD6335	Approved
0.6581	Remote Similarity	NPD7328	Approved
0.6581	Remote Similarity	NPD7327	Approved
0.6574	Remote Similarity	NPD5223	Approved
0.6566	Remote Similarity	NPD4197	Approved
0.6562	Remote Similarity	NPD7645	Phase 2
0.6559	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6555	Remote Similarity	NPD6015	Approved
0.6555	Remote Similarity	NPD6016	Approved
0.6552	Remote Similarity	NPD6868	Approved
0.6538	Remote Similarity	NPD5778	Approved
0.6538	Remote Similarity	NPD5779	Approved
0.6525	Remote Similarity	NPD7101	Approved
0.6525	Remote Similarity	NPD7516	Approved
0.6525	Remote Similarity	NPD7100	Approved
0.6522	Remote Similarity	NPD4632	Approved
0.6514	Remote Similarity	NPD7632	Discontinued
0.6514	Remote Similarity	NPD5224	Approved
0.6514	Remote Similarity	NPD5211	Phase 2
0.6514	Remote Similarity	NPD5225	Approved
0.6514	Remote Similarity	NPD5226	Approved
0.6514	Remote Similarity	NPD4633	Approved
0.6509	Remote Similarity	NPD7614	Phase 1
0.6505	Remote Similarity	NPD5692	Phase 3
0.65	Remote Similarity	NPD5988	Approved
0.6496	Remote Similarity	NPD6317	Approved
0.6495	Remote Similarity	NPD5368	Approved
0.6489	Remote Similarity	NPD6942	Approved
0.6489	Remote Similarity	NPD7339	Approved
0.6489	Remote Similarity	NPD8039	Approved
0.6481	Remote Similarity	NPD4700	Approved
0.6471	Remote Similarity	NPD8294	Approved
0.6471	Remote Similarity	NPD8377	Approved
0.6458	Remote Similarity	NPD6114	Approved
0.6458	Remote Similarity	NPD6118	Approved
0.6458	Remote Similarity	NPD3617	Approved
0.6458	Remote Similarity	NPD6697	Approved
0.6458	Remote Similarity	NPD6115	Approved
0.6455	Remote Similarity	NPD5174	Approved
0.6455	Remote Similarity	NPD5175	Approved
0.6441	Remote Similarity	NPD6314	Approved
0.6441	Remote Similarity	NPD6313	Approved
0.6436	Remote Similarity	NPD5690	Phase 2
0.6436	Remote Similarity	NPD4690	Approved
0.6436	Remote Similarity	NPD5205	Approved
0.6436	Remote Similarity	NPD4689	Approved
0.6436	Remote Similarity	NPD4138	Approved
0.6436	Remote Similarity	NPD4693	Phase 3
0.6436	Remote Similarity	NPD4688	Approved
0.6421	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6417	Remote Similarity	NPD8380	Approved
0.6417	Remote Similarity	NPD8378	Approved
0.6417	Remote Similarity	NPD8379	Approved
0.6417	Remote Similarity	NPD8033	Approved
0.6417	Remote Similarity	NPD8296	Approved
0.6417	Remote Similarity	NPD8335	Approved
0.641	Remote Similarity	NPD6274	Approved
0.6408	Remote Similarity	NPD6051	Approved
0.64	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6396	Remote Similarity	NPD5141	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