NPASS Compound

Structure

NPC263780 OpenBabel07101718192D 33 37 0 0 1 0 0 0 0 0999 V2000 -3.4641 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 C 0 0 0 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 -1.7321 4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 0.0000 0.0000 C 0 0 0 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 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 2.0000 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 0.0000 -1.0000 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 -0.0000 2.0000 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 2.5981 -2.5000 0.0000 C 0 0 0 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 4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -3.0000 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 -0.8660 0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.3301 -2.5000 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 1.7321 -1.0000 0.0000 C 0 0 2 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 0.0000 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.4641 -4.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 17 2 0 0 0 0 2 18 1 0 0 0 0 4 27 1 0 0 0 0 6 33 1 0 0 0 0 7 8 1 0 0 0 0 7 19 2 0 0 0 0 8 22 2 0 0 0 0 9 10 1 0 0 0 0 9 17 1 0 0 0 0 10 29 1 0 0 0 0 11 12 1 0 0 0 0 11 26 1 0 0 0 0 12 28 1 0 0 0 0 13 14 1 0 0 0 0 13 27 1 0 0 0 0 14 29 1 0 0 0 0 15 17 1 0 0 0 0 15 23 1 0 0 0 0 16 20 2 0 0 0 0 16 21 1 0 0 0 0 18 19 1 0 0 0 0 18 24 2 0 0 0 0 19 20 1 0 0 0 0 20 26 1 0 0 0 0 21 24 1 0 0 0 0 21 30 2 0 0 0 0 22 26 1 0 0 0 0 22 27 1 0 0 0 0 23 28 1 6 0 0 0 23 29 1 0 0 0 0 24 31 1 0 0 0 0 25 32 2 0 0 0 0 25 33 1 0 0 0 0 26 3 1 1 0 0 0 27 28 1 1 0 0 0 28 5 1 6 0 0 0 29 25 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	448.26
Volume:	484.063
LogP:	5.114
LogD:	3.303
LogS:	-4.282
# Rotatable Bonds:	2
TPSA:	66.76
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	5
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.374
Synthetic Accessibility Score:	5.076
Fsp3:	0.552
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.863
MDCK Permeability:	2.2172087483340874e-05
Pgp-inhibitor:	0.053
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.953
30% Bioavailability (F30%):	0.06

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.071
Plasma Protein Binding (PPB):	96.052001953125%
Volume Distribution (VD):	1.386
Pgp-substrate:	5.770342826843262%

ADMET: Metabolism

CYP1A2-inhibitor:	0.104
CYP1A2-substrate:	0.925
CYP2C19-inhibitor:	0.095
CYP2C19-substrate:	0.784
CYP2C9-inhibitor:	0.185
CYP2C9-substrate:	0.221
CYP2D6-inhibitor:	0.428
CYP2D6-substrate:	0.12
CYP3A4-inhibitor:	0.645
CYP3A4-substrate:	0.909

ADMET: Excretion

Clearance (CL):	8.886
Half-life (T1/2):	0.486

ADMET: Toxicity

hERG Blockers:	0.107
Human Hepatotoxicity (H-HT):	0.66
Drug-inuced Liver Injury (DILI):	0.045
AMES Toxicity:	0.199
Rat Oral Acute Toxicity:	0.366
Maximum Recommended Daily Dose:	0.839
Skin Sensitization:	0.053
Carcinogencity:	0.908
Eye Corrosion:	0.003
Eye Irritation:	0.1
Respiratory Toxicity:	0.939

Download Data

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

Natural Product: NPC263780

Natural Product ID:	NPC263780
*Common Name:**	17-(Methoxycarbonyl)-28-Nor-Isoiguesterin
IUPAC Name:	methyl (4aS,6aR,6aS,14aS,14bS)-10-hydroxy-6a,6a,9,14a-tetramethyl-2-methylidene-11-oxo-1,3,4,5,6,13,14,14b-octahydropicene-4a-carboxylate
Synonyms:
Standard InCHIKey:	CPFUJAKVJBYWJA-BTRWLOMLSA-N
Standard InCHI:	InChI=1S/C29H36O4/c1-17-9-10-29(25(32)33-6)14-13-27(4)22-8-7-19-18(2)24(31)21(30)16-20(19)26(22,3)11-12-28(27,5)23(29)15-17/h7-8,16,23,31H,1,9-15H2,2-6H3/t23-,26-,27+,28-,29-/m0/s1
SMILES:	C=C1CC[C@@]2(CC[C@]3(C)C4=CC=C5C(=C(C(=O)C=C5[C@]4(C)CC[C@@]3(C)[C@@H]2C1)O)C)C(=O)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL515027
PubChem CID:	10411393
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000264] Organic acids and derivatives [CHEMONTID:0000265] Carboxylic acids and derivatives [CHEMONTID:0001093] Carboxylic acid derivatives [CHEMONTID:0001238] Carboxylic acid esters [CHEMONTID:0003416] Methyl esters

*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
NPO26085	Salacia kraussii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9644053]
NPO26085	Salacia kraussii	Species	Celastraceae	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	3

Activity Type	# Activity
Cell Line	1
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT139	Cell Line	HT-29	Homo sapiens	IC50	=	2.38	ug.mL-1	PMID[488465]
NPT485	Organism	Plasmodium falciparum (isolate K1 / Thailand)	Plasmodium falciparum K1	IC50	=	0.0276	ug.mL-1	PMID[488465]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	0.0371	ug.mL-1	PMID[488465]

☑ 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 NPC263780 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	199
0.1-0.2	1128
0.2-0.3	4243
0.3-0.4	11825
0.4-0.5	12284
0.5-0.6	6900
0.6-0.7	4780
0.7-0.8	1181
0.8-0.85	124
0.85-0.9	25
0.9-0.95	2
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
0.9884	High Similarity	NPC470036
0.9884	High Similarity	NPC174167
0.9651	High Similarity	NPC112454
0.9551	High Similarity	NPC777
0.8989	High Similarity	NPC68148
0.8989	High Similarity	NPC65615
0.8966	High Similarity	NPC474680
0.8953	High Similarity	NPC53733
0.8913	High Similarity	NPC147232
0.8901	High Similarity	NPC211230
0.8851	High Similarity	NPC96095
0.8804	High Similarity	NPC474882
0.8763	High Similarity	NPC213366
0.875	High Similarity	NPC474537
0.8736	High Similarity	NPC105803
0.8736	High Similarity	NPC70834
0.8721	High Similarity	NPC475863
0.8721	High Similarity	NPC471898
0.8636	High Similarity	NPC53385
0.8621	High Similarity	NPC251779
0.8621	High Similarity	NPC69101
0.8605	High Similarity	NPC287063
0.8605	High Similarity	NPC104545
0.8602	High Similarity	NPC23170
0.8602	High Similarity	NPC474328
0.8571	High Similarity	NPC477973
0.8571	High Similarity	NPC474700
0.8539	High Similarity	NPC33881
0.8539	High Similarity	NPC132228
0.8539	High Similarity	NPC6185
0.8539	High Similarity	NPC263997
0.8539	High Similarity	NPC241512
0.8539	High Similarity	NPC8518
0.8523	High Similarity	NPC291999
0.8523	High Similarity	NPC200752
0.8523	High Similarity	NPC309309
0.8506	High Similarity	NPC278459
0.8506	High Similarity	NPC274050
0.8506	High Similarity	NPC470034
0.8506	High Similarity	NPC267691
0.8506	High Similarity	NPC162632
0.8506	High Similarity	NPC142244
0.8506	High Similarity	NPC225515
0.8506	High Similarity	NPC55869
0.8506	High Similarity	NPC263272
0.8495	Intermediate Similarity	NPC295643
0.8495	Intermediate Similarity	NPC272075
0.8495	Intermediate Similarity	NPC214756
0.8488	Intermediate Similarity	NPC199595
0.8488	Intermediate Similarity	NPC192329
0.8478	Intermediate Similarity	NPC46441
0.8478	Intermediate Similarity	NPC252737
0.8469	Intermediate Similarity	NPC179208
0.8462	Intermediate Similarity	NPC1753
0.8462	Intermediate Similarity	NPC474511
0.8462	Intermediate Similarity	NPC474474
0.8404	Intermediate Similarity	NPC80365
0.8404	Intermediate Similarity	NPC74751
0.8391	Intermediate Similarity	NPC37038
0.8391	Intermediate Similarity	NPC18955
0.8391	Intermediate Similarity	NPC108955
0.8391	Intermediate Similarity	NPC267517
0.8391	Intermediate Similarity	NPC477057
0.8387	Intermediate Similarity	NPC301244
0.8387	Intermediate Similarity	NPC233455
0.8387	Intermediate Similarity	NPC4036
0.8387	Intermediate Similarity	NPC474525
0.8387	Intermediate Similarity	NPC65120
0.8387	Intermediate Similarity	NPC145067
0.8387	Intermediate Similarity	NPC158030
0.8372	Intermediate Similarity	NPC260385
0.8372	Intermediate Similarity	NPC280654
0.8372	Intermediate Similarity	NPC110094
0.8352	Intermediate Similarity	NPC477228
0.8352	Intermediate Similarity	NPC173089
0.8352	Intermediate Similarity	NPC158141
0.8352	Intermediate Similarity	NPC71507
0.8333	Intermediate Similarity	NPC469993
0.8316	Intermediate Similarity	NPC295347
0.8295	Intermediate Similarity	NPC121984
0.828	Intermediate Similarity	NPC198818
0.828	Intermediate Similarity	NPC474728
0.8276	Intermediate Similarity	NPC16394
0.8276	Intermediate Similarity	NPC231431
0.8276	Intermediate Similarity	NPC27817
0.8256	Intermediate Similarity	NPC107039
0.8256	Intermediate Similarity	NPC165711
0.8256	Intermediate Similarity	NPC471899
0.8256	Intermediate Similarity	NPC472300
0.8256	Intermediate Similarity	NPC471897
0.8242	Intermediate Similarity	NPC324063
0.8242	Intermediate Similarity	NPC56588
0.8229	Intermediate Similarity	NPC62516
0.8229	Intermediate Similarity	NPC269492
0.8229	Intermediate Similarity	NPC9487
0.8229	Intermediate Similarity	NPC157113
0.8229	Intermediate Similarity	NPC98874
0.8222	Intermediate Similarity	NPC156981
0.8222	Intermediate Similarity	NPC312660
0.8202	Intermediate Similarity	NPC310989
0.8202	Intermediate Similarity	NPC103486
0.8191	Intermediate Similarity	NPC77099
0.8191	Intermediate Similarity	NPC230064
0.8191	Intermediate Similarity	NPC38754
0.8191	Intermediate Similarity	NPC470590
0.8191	Intermediate Similarity	NPC60755
0.8191	Intermediate Similarity	NPC285184
0.8182	Intermediate Similarity	NPC2482
0.8172	Intermediate Similarity	NPC474686
0.8172	Intermediate Similarity	NPC198664
0.8172	Intermediate Similarity	NPC474972
0.8172	Intermediate Similarity	NPC95246
0.8172	Intermediate Similarity	NPC36668
0.8172	Intermediate Similarity	NPC274330
0.8172	Intermediate Similarity	NPC143232
0.8172	Intermediate Similarity	NPC470588
0.8172	Intermediate Similarity	NPC161751
0.8172	Intermediate Similarity	NPC281524
0.8172	Intermediate Similarity	NPC118011
0.8161	Intermediate Similarity	NPC189485
0.8161	Intermediate Similarity	NPC30321
0.8161	Intermediate Similarity	NPC321514
0.8161	Intermediate Similarity	NPC74410
0.8144	Intermediate Similarity	NPC208094
0.8144	Intermediate Similarity	NPC21728
0.8144	Intermediate Similarity	NPC26413
0.8144	Intermediate Similarity	NPC473456
0.814	Intermediate Similarity	NPC112680
0.814	Intermediate Similarity	NPC309399
0.814	Intermediate Similarity	NPC92080
0.814	Intermediate Similarity	NPC180886
0.814	Intermediate Similarity	NPC899
0.814	Intermediate Similarity	NPC89294
0.8132	Intermediate Similarity	NPC133652
0.8125	Intermediate Similarity	NPC139570
0.8125	Intermediate Similarity	NPC139459
0.8125	Intermediate Similarity	NPC148523
0.8111	Intermediate Similarity	NPC470015
0.8111	Intermediate Similarity	NPC102197
0.8111	Intermediate Similarity	NPC69279
0.8111	Intermediate Similarity	NPC83569
0.8111	Intermediate Similarity	NPC168188
0.8105	Intermediate Similarity	NPC133579
0.8105	Intermediate Similarity	NPC169343
0.8105	Intermediate Similarity	NPC474806
0.809	Intermediate Similarity	NPC474085
0.809	Intermediate Similarity	NPC3915
0.809	Intermediate Similarity	NPC221647
0.8085	Intermediate Similarity	NPC126369
0.8085	Intermediate Similarity	NPC111110
0.8085	Intermediate Similarity	NPC193750
0.8085	Intermediate Similarity	NPC120840
0.8085	Intermediate Similarity	NPC113989
0.8085	Intermediate Similarity	NPC291028
0.8085	Intermediate Similarity	NPC470589
0.8065	Intermediate Similarity	NPC470629
0.8065	Intermediate Similarity	NPC181225
0.8065	Intermediate Similarity	NPC290690
0.8065	Intermediate Similarity	NPC182797
0.8065	Intermediate Similarity	NPC246708
0.8065	Intermediate Similarity	NPC230387
0.8065	Intermediate Similarity	NPC474512
0.8065	Intermediate Similarity	NPC72397
0.8065	Intermediate Similarity	NPC40552
0.8065	Intermediate Similarity	NPC52169
0.8065	Intermediate Similarity	NPC473242
0.8065	Intermediate Similarity	NPC17733
0.8061	Intermediate Similarity	NPC478056
0.8061	Intermediate Similarity	NPC471966
0.8041	Intermediate Similarity	NPC88847
0.8022	Intermediate Similarity	NPC180834
0.8021	Intermediate Similarity	NPC148964
0.8021	Intermediate Similarity	NPC160413
0.8	Intermediate Similarity	NPC260956
0.8	Intermediate Similarity	NPC471588
0.8	Intermediate Similarity	NPC321289
0.8	Intermediate Similarity	NPC187722
0.8	Intermediate Similarity	NPC327969
0.8	Intermediate Similarity	NPC204341
0.8	Intermediate Similarity	NPC473986
0.8	Intermediate Similarity	NPC474018
0.8	Intermediate Similarity	NPC320514
0.8	Intermediate Similarity	NPC6255
0.8	Intermediate Similarity	NPC105189
0.7979	Intermediate Similarity	NPC225585
0.7979	Intermediate Similarity	NPC234346
0.7979	Intermediate Similarity	NPC64872
0.7979	Intermediate Similarity	NPC130520
0.7979	Intermediate Similarity	NPC121798
0.7979	Intermediate Similarity	NPC263393
0.7979	Intermediate Similarity	NPC469546
0.7979	Intermediate Similarity	NPC475049
0.7979	Intermediate Similarity	NPC61543
0.7979	Intermediate Similarity	NPC30522
0.7979	Intermediate Similarity	NPC293048
0.7979	Intermediate Similarity	NPC290972
0.7979	Intermediate Similarity	NPC25906
0.7979	Intermediate Similarity	NPC270768
0.7979	Intermediate Similarity	NPC59263
0.7979	Intermediate Similarity	NPC127689

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 NPC263780 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	183
0.1-0.2	1332
0.2-0.3	3560
0.3-0.4	2656
0.4-0.5	927
0.5-0.6	245
0.6-0.7	179
0.7-0.8	63
0.8-0.85	4
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9651	High Similarity	NPD7285	Clinical (unspecified phase)
0.8404	Intermediate Similarity	NPD7748	Approved
0.8391	Intermediate Similarity	NPD4695	Discontinued
0.8387	Intermediate Similarity	NPD7515	Phase 2
0.8144	Intermediate Similarity	NPD7902	Approved
0.8065	Intermediate Similarity	NPD6672	Approved
0.8065	Intermediate Similarity	NPD5737	Approved
0.8	Intermediate Similarity	NPD6050	Approved
0.7959	Intermediate Similarity	NPD6084	Phase 2
0.7959	Intermediate Similarity	NPD6083	Phase 2
0.7938	Intermediate Similarity	NPD5695	Phase 3
0.7895	Intermediate Similarity	NPD5692	Phase 3
0.7872	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7857	Intermediate Similarity	NPD7614	Phase 1
0.7849	Intermediate Similarity	NPD5280	Approved
0.7849	Intermediate Similarity	NPD4694	Approved
0.7849	Intermediate Similarity	NPD5279	Phase 3
0.7835	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7835	Intermediate Similarity	NPD7900	Approved
0.7812	Intermediate Similarity	NPD5694	Approved
0.7812	Intermediate Similarity	NPD5281	Approved
0.7812	Intermediate Similarity	NPD5284	Approved
0.7789	Intermediate Similarity	NPD6904	Approved
0.7789	Intermediate Similarity	NPD6080	Approved
0.7789	Intermediate Similarity	NPD6673	Approved
0.7753	Intermediate Similarity	NPD3617	Approved
0.7742	Intermediate Similarity	NPD5329	Approved
0.7732	Intermediate Similarity	NPD6399	Phase 3
0.77	Intermediate Similarity	NPD5696	Approved
0.7677	Intermediate Similarity	NPD7732	Phase 3
0.766	Intermediate Similarity	NPD7334	Approved
0.766	Intermediate Similarity	NPD6409	Approved
0.766	Intermediate Similarity	NPD5330	Approved
0.766	Intermediate Similarity	NPD7146	Approved
0.766	Intermediate Similarity	NPD6684	Approved
0.766	Intermediate Similarity	NPD7521	Approved
0.7634	Intermediate Similarity	NPD4197	Approved
0.7604	Intermediate Similarity	NPD4753	Phase 2
0.75	Intermediate Similarity	NPD6903	Approved
0.7474	Intermediate Similarity	NPD6098	Approved
0.7474	Intermediate Similarity	NPD5690	Phase 2
0.7449	Intermediate Similarity	NPD5693	Phase 1
0.7449	Intermediate Similarity	NPD6411	Approved
0.7447	Intermediate Similarity	NPD3665	Phase 1
0.7447	Intermediate Similarity	NPD3666	Approved
0.7447	Intermediate Similarity	NPD4786	Approved
0.7447	Intermediate Similarity	NPD3133	Approved
0.7429	Intermediate Similarity	NPD6675	Approved
0.7429	Intermediate Similarity	NPD7128	Approved
0.7429	Intermediate Similarity	NPD6402	Approved
0.7429	Intermediate Similarity	NPD5739	Approved
0.7419	Intermediate Similarity	NPD4223	Phase 3
0.7419	Intermediate Similarity	NPD3667	Approved
0.7419	Intermediate Similarity	NPD4221	Approved
0.74	Intermediate Similarity	NPD5654	Approved
0.7396	Intermediate Similarity	NPD3573	Approved
0.7347	Intermediate Similarity	NPD5207	Approved
0.7292	Intermediate Similarity	NPD3618	Phase 1
0.729	Intermediate Similarity	NPD6881	Approved
0.729	Intermediate Similarity	NPD7320	Approved
0.729	Intermediate Similarity	NPD6899	Approved
0.7255	Intermediate Similarity	NPD5959	Approved
0.7245	Intermediate Similarity	NPD5328	Approved
0.7245	Intermediate Similarity	NPD6101	Approved
0.7245	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7228	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7228	Intermediate Similarity	NPD5210	Approved
0.7228	Intermediate Similarity	NPD4629	Approved
0.7222	Intermediate Similarity	NPD6372	Approved
0.7222	Intermediate Similarity	NPD6373	Approved
0.7204	Intermediate Similarity	NPD8259	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD5133	Approved
0.7196	Intermediate Similarity	NPD5697	Approved
0.7196	Intermediate Similarity	NPD5701	Approved
0.7157	Intermediate Similarity	NPD5221	Approved
0.7157	Intermediate Similarity	NPD5222	Approved
0.7157	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7157	Intermediate Similarity	NPD4697	Phase 3
0.7156	Intermediate Similarity	NPD7290	Approved
0.7156	Intermediate Similarity	NPD6883	Approved
0.7156	Intermediate Similarity	NPD7102	Approved
0.7143	Intermediate Similarity	NPD5208	Approved
0.713	Intermediate Similarity	NPD6011	Approved
0.7113	Intermediate Similarity	NPD4689	Approved
0.7113	Intermediate Similarity	NPD4623	Approved
0.7113	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7113	Intermediate Similarity	NPD4693	Phase 3
0.7113	Intermediate Similarity	NPD4519	Discontinued
0.7113	Intermediate Similarity	NPD4690	Approved
0.7113	Intermediate Similarity	NPD4138	Approved
0.7113	Intermediate Similarity	NPD5205	Approved
0.7113	Intermediate Similarity	NPD4688	Approved
0.7111	Intermediate Similarity	NPD5733	Approved
0.71	Intermediate Similarity	NPD6079	Approved
0.7091	Intermediate Similarity	NPD6650	Approved
0.7091	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD8130	Phase 1
0.7091	Intermediate Similarity	NPD6847	Approved
0.7091	Intermediate Similarity	NPD6869	Approved
0.7091	Intermediate Similarity	NPD6649	Approved
0.7091	Intermediate Similarity	NPD6617	Approved
0.7087	Intermediate Similarity	NPD5173	Approved
0.7087	Intermediate Similarity	NPD4755	Approved
0.7083	Intermediate Similarity	NPD3668	Phase 3
0.7065	Intermediate Similarity	NPD4756	Discovery
0.7064	Intermediate Similarity	NPD6012	Approved
0.7064	Intermediate Similarity	NPD6014	Approved
0.7064	Intermediate Similarity	NPD6013	Approved
0.7053	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD8297	Approved
0.7027	Intermediate Similarity	NPD6882	Approved
0.7019	Intermediate Similarity	NPD7638	Approved
0.701	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD4096	Approved
0.6979	Remote Similarity	NPD4788	Approved
0.697	Remote Similarity	NPD4518	Approved
0.6952	Remote Similarity	NPD6404	Discontinued
0.6952	Remote Similarity	NPD7639	Approved
0.6952	Remote Similarity	NPD5285	Approved
0.6952	Remote Similarity	NPD5286	Approved
0.6952	Remote Similarity	NPD4700	Approved
0.6952	Remote Similarity	NPD4696	Approved
0.6952	Remote Similarity	NPD7640	Approved
0.6931	Remote Similarity	NPD8035	Phase 2
0.6931	Remote Similarity	NPD8034	Phase 2
0.6923	Remote Similarity	NPD4058	Approved
0.6923	Remote Similarity	NPD4687	Approved
0.6915	Remote Similarity	NPD7645	Phase 2
0.6889	Remote Similarity	NPD5276	Approved
0.6887	Remote Similarity	NPD5223	Approved
0.6881	Remote Similarity	NPD6412	Phase 2
0.6864	Remote Similarity	NPD8328	Phase 3
0.6863	Remote Similarity	NPD5779	Approved
0.6863	Remote Similarity	NPD5778	Approved
0.6863	Remote Similarity	NPD4202	Approved
0.6854	Remote Similarity	NPD4137	Phase 3
0.6842	Remote Similarity	NPD6868	Approved
0.6822	Remote Similarity	NPD5211	Phase 2
0.6822	Remote Similarity	NPD5225	Approved
0.6822	Remote Similarity	NPD5224	Approved
0.6822	Remote Similarity	NPD4633	Approved
0.6822	Remote Similarity	NPD5226	Approved
0.6814	Remote Similarity	NPD4632	Approved
0.6796	Remote Similarity	NPD6001	Approved
0.6783	Remote Similarity	NPD7115	Discovery
0.6778	Remote Similarity	NPD4747	Approved
0.6778	Remote Similarity	NPD4691	Approved
0.6771	Remote Similarity	NPD8028	Phase 2
0.6759	Remote Similarity	NPD4754	Approved
0.6759	Remote Similarity	NPD5174	Approved
0.6759	Remote Similarity	NPD5175	Approved
0.6737	Remote Similarity	NPD4195	Approved
0.6727	Remote Similarity	NPD6614	Approved
0.6724	Remote Similarity	NPD6335	Approved
0.6697	Remote Similarity	NPD5141	Approved
0.6696	Remote Similarity	NPD6274	Approved
0.6667	Remote Similarity	NPD7100	Approved
0.6667	Remote Similarity	NPD7094	Approved
0.6667	Remote Similarity	NPD7101	Approved
0.6667	Remote Similarity	NPD6858	Approved
0.6667	Remote Similarity	NPD5091	Approved
0.6638	Remote Similarity	NPD6317	Approved
0.6638	Remote Similarity	NPD6009	Approved
0.6636	Remote Similarity	NPD6008	Approved
0.6636	Remote Similarity	NPD4768	Approved
0.6636	Remote Similarity	NPD4767	Approved
0.6607	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6606	Remote Similarity	NPD6052	Approved
0.6598	Remote Similarity	NPD4139	Approved
0.6598	Remote Similarity	NPD4692	Approved
0.6581	Remote Similarity	NPD6314	Approved
0.6581	Remote Similarity	NPD6313	Approved
0.6555	Remote Similarity	NPD6909	Approved
0.6555	Remote Similarity	NPD6908	Approved
0.6552	Remote Similarity	NPD2664	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD6081	Approved
0.6518	Remote Similarity	NPD6686	Approved
0.6518	Remote Similarity	NPD5168	Approved
0.6518	Remote Similarity	NPD4729	Approved
0.6518	Remote Similarity	NPD4730	Approved
0.6518	Remote Similarity	NPD5128	Approved
0.6517	Remote Similarity	NPD7331	Phase 2
0.6517	Remote Similarity	NPD4224	Phase 2
0.6504	Remote Similarity	NPD7736	Approved
0.65	Remote Similarity	NPD1696	Phase 3
0.65	Remote Similarity	NPD1694	Approved
0.6496	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6489	Remote Similarity	NPD6942	Approved
0.6489	Remote Similarity	NPD7339	Approved
0.6489	Remote Similarity	NPD8039	Approved
0.648	Remote Similarity	NPD7260	Phase 2
0.6476	Remote Similarity	NPD5282	Discontinued
0.6471	Remote Similarity	NPD6319	Approved
0.6446	Remote Similarity	NPD7604	Phase 2
0.6442	Remote Similarity	NPD7637	Suspended
0.6421	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6417	Remote Similarity	NPD5983	Phase 2
0.6417	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6413	Remote Similarity	NPD4789	Approved
0.6404	Remote Similarity	NPD4634	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