NPASS Compound

Structure

CID269729 OpenBabel06191716072D 31 34 0 0 1 0 0 0 0 0999 V2000 2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9641 -3.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9641 -3.8660 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 0.0000 -2.0000 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 4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 C 0 0 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 1.7321 -3.0000 0.0000 C 0 0 0 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 3.4641 -1.0000 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 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 -0.8660 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 -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 2.5981 -2.5000 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 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 3.4641 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 C 0 0 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 -0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.4641 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 2.0000 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 0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 17 1 0 0 0 0 2 24 1 0 0 0 0 3 24 1 0 0 0 0 7 11 1 0 0 0 0 7 12 1 0 0 0 0 8 9 1 0 0 0 0 8 18 2 0 0 0 0 9 21 1 0 0 0 0 10 13 1 0 0 0 0 10 20 1 0 0 0 0 11 24 1 0 0 0 0 12 25 1 0 0 0 0 13 26 1 0 0 0 0 14 22 1 0 0 0 0 14 23 1 0 0 0 0 15 18 1 0 0 0 0 15 28 2 0 0 0 0 16 19 1 0 0 0 0 16 29 2 0 0 0 0 17 30 2 0 0 0 0 17 31 1 0 0 0 0 18 19 1 0 0 0 0 19 27 1 6 0 0 0 20 24 1 0 0 0 0 20 25 1 6 0 0 0 21 26 1 6 0 0 0 21 27 1 0 0 0 0 22 25 1 6 0 0 0 22 26 1 0 0 0 0 23 27 1 1 0 0 0 23 31 1 0 0 0 0 25 4 1 6 0 0 0 26 5 1 6 0 0 0 27 6 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	428.29
Volume:	465.937
LogP:	4.556
LogD:	3.951
LogS:	-4.5
# Rotatable Bonds:	4
TPSA:	60.44
# H-Bond Aceptor:	4
# H-Bond Donor:	0
# Rings:	4
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.437
Synthetic Accessibility Score:	4.832
Fsp3:	0.815
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.784
MDCK Permeability:	2.0271671019145288e-05
Pgp-inhibitor:	0.998
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.01
20% Bioavailability (F20%):	0.982
30% Bioavailability (F30%):	0.971

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.978
Plasma Protein Binding (PPB):	59.626922607421875%
Volume Distribution (VD):	2.439
Pgp-substrate:	39.1817741394043%

ADMET: Metabolism

CYP1A2-inhibitor:	0.019
CYP1A2-substrate:	0.112
CYP2C19-inhibitor:	0.033
CYP2C19-substrate:	0.568
CYP2C9-inhibitor:	0.095
CYP2C9-substrate:	0.057
CYP2D6-inhibitor:	0.012
CYP2D6-substrate:	0.18
CYP3A4-inhibitor:	0.661
CYP3A4-substrate:	0.349

ADMET: Excretion

Clearance (CL):	3.775
Half-life (T1/2):	0.13

ADMET: Toxicity

hERG Blockers:	0.088
Human Hepatotoxicity (H-HT):	0.43
Drug-inuced Liver Injury (DILI):	0.079
AMES Toxicity:	0.026
Rat Oral Acute Toxicity:	0.148
Maximum Recommended Daily Dose:	0.938
Skin Sensitization:	0.961
Carcinogencity:	0.195
Eye Corrosion:	0.978
Eye Irritation:	0.798
Respiratory Toxicity:	0.984

Download Data

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

Natural Product: NPC269729

Natural Product ID:	NPC269729
*Common Name:**	Scalaradial
IUPAC Name:	[(4aS,4bR,6S,6aS,7R,10aS,10bR,12aS)-7,8-diformyl-1,1,4a,6a,10b-pentamethyl-2,3,4,4b,5,6,7,10,10a,11,12,12a-dodecahydrochrysen-6-yl] acetate
Synonyms:	Scalaradial
Standard InCHIKey:	ADWFEADZGIHPDE-QGERINELSA-N
Standard InCHI:	InChI=1S/C27H40O4/c1-17(30)31-23-14-22-25(4)12-7-11-24(2,3)20(25)10-13-26(22,5)21-9-8-18(15-28)19(16-29)27(21,23)6/h8,15-16,19-23H,7,9-14H2,1-6H3/t19-,20-,21-,22+,23-,25-,26-,27+/m0/s1
SMILES:	O=C[C@H]1C(=CC[C@@H]2[C@]1(C)[C@@H](OC(=O)C)C[C@H]1[C@@]2(C)CC[C@@H]2[C@]1(C)CCCC2(C)C)C=O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL487005
PubChem CID:	21637538
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001552] Sesterterpenoids [CHEMONTID:0002883] Scalarane sesterterpenoids

*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
NPO33388	glossodoris sedna	Species	Chromodorididae	Eukaryota	n.a.	n.a.	n.a.	PMID[10785432]
NPO12784	Glossodoris rufomarginata	Species	Chromodorididae	Eukaryota	n.a.	South China Sea	n.a.	PMID[15620263]
NPO6350	Spongia officinalis	Species	Spongiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[21548580]
NPO6350	Spongia officinalis	Species	Spongiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[31095383]
NPO23862	Cacospongia mollior	Species	Thorectidae	Eukaryota	n.a.	n.a.	n.a.	PMID[8176402]
NPO23862	Cacospongia mollior	Species	Thorectidae	Eukaryota	n.a.	n.a.	n.a.	Database[Title]
NPO12784	Glossodoris rufomarginata	Species	Chromodorididae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23862	Cacospongia mollior	Species	Thorectidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6350	Spongia officinalis	Species	Spongiidae	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	11
LD50	1

Activity Type	# Activity
Individual Protein	3
Organism	3
Others	3
SINGLE PROTEIN	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT3172	Individual Protein	Phospholipase A2 group IIA	Homo sapiens	IC50	=	15.0	nM	PMID[520197]
NPT4422	Individual Protein	Phospholipase A2 (Bee)	Apis mellifera	IC50	=	70.0	nM	PMID[520202]
NPT4506	Individual Protein	Transient receptor potential cation channel subfamily M member 2	Homo sapiens	IC50	=	210.0	nM	PMID[520202]
NPT27	Others	Unspecified		IC50	=	40.0	nM	PMID[520197]
NPT605	Organism	Homo sapiens	Homo sapiens	IC50	=	1000.0	nM	PMID[520197]
NPT2	Others	Unspecified		IC50	=	600.0	nM	PMID[520198]
NPT176	Organism	Artemia salina	Artemia salina	LD50	=	0.18	ug ml-1	PMID[520200]
NPT24397	SINGLE PROTEIN	Phospholipase A2	Apis mellifera	IC50	=	70.0	nM	PMID[520201]
NPT2	Others	Unspecified		IC50	=	5400.0	nM	PMID[520202]
NPT22927	SINGLE PROTEIN	Transient receptor potential cation channel subfamily M member 7	Mus musculus	IC50	=	760.0	nM	PMID[520202]
NPT27014	SINGLE PROTEIN	Transient receptor potential cation channel subfamily M member 2	Rattus norvegicus	IC50	=	330.0	nM	PMID[520202]

☑ 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 NPC269729 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	240
0.1-0.2	1585
0.2-0.3	5379
0.3-0.4	11988
0.4-0.5	10444
0.5-0.6	6528
0.6-0.7	4822
0.7-0.8	1552
0.8-0.85	128
0.85-0.9	22
0.9-0.95	6
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9886	High Similarity	NPC274417
0.9655	High Similarity	NPC328141
0.9457	High Similarity	NPC475392
0.9457	High Similarity	NPC475202
0.9457	High Similarity	NPC475385
0.9158	High Similarity	NPC282233
0.9158	High Similarity	NPC95585
0.9011	High Similarity	NPC474185
0.8889	High Similarity	NPC469546
0.8864	High Similarity	NPC2709
0.8791	High Similarity	NPC159748
0.8791	High Similarity	NPC101651
0.8778	High Similarity	NPC224145
0.8737	High Similarity	NPC471966
0.8736	High Similarity	NPC470813
0.8723	High Similarity	NPC469545
0.8723	High Similarity	NPC61369
0.8723	High Similarity	NPC471039
0.8723	High Similarity	NPC5532
0.871	High Similarity	NPC471040
0.8667	High Similarity	NPC46912
0.8667	High Similarity	NPC162107
0.8632	High Similarity	NPC473456
0.8632	High Similarity	NPC226986
0.8602	High Similarity	NPC151722
0.8602	High Similarity	NPC79117
0.8571	High Similarity	NPC254202
0.8571	High Similarity	NPC474925
0.8556	High Similarity	NPC91525
0.8556	High Similarity	NPC10005
0.8556	High Similarity	NPC9892
0.8556	High Similarity	NPC329943
0.8511	High Similarity	NPC74751
0.8495	Intermediate Similarity	NPC230064
0.8478	Intermediate Similarity	NPC475049
0.8462	Intermediate Similarity	NPC30421
0.8438	Intermediate Similarity	NPC292133
0.8438	Intermediate Similarity	NPC23680
0.8421	Intermediate Similarity	NPC139570
0.8404	Intermediate Similarity	NPC214756
0.8404	Intermediate Similarity	NPC295643
0.8404	Intermediate Similarity	NPC272075
0.8387	Intermediate Similarity	NPC113989
0.8387	Intermediate Similarity	NPC120840
0.8387	Intermediate Similarity	NPC474728
0.837	Intermediate Similarity	NPC473229
0.837	Intermediate Similarity	NPC206060
0.837	Intermediate Similarity	NPC474845
0.8352	Intermediate Similarity	NPC471042
0.8351	Intermediate Similarity	NPC194196
0.8351	Intermediate Similarity	NPC478056
0.83	Intermediate Similarity	NPC189616
0.83	Intermediate Similarity	NPC470297
0.8298	Intermediate Similarity	NPC145067
0.8298	Intermediate Similarity	NPC285184
0.8298	Intermediate Similarity	NPC470590
0.8298	Intermediate Similarity	NPC158030
0.8298	Intermediate Similarity	NPC65120
0.8298	Intermediate Similarity	NPC77099
0.8298	Intermediate Similarity	NPC218301
0.8298	Intermediate Similarity	NPC60755
0.8298	Intermediate Similarity	NPC4036
0.8298	Intermediate Similarity	NPC233455
0.8295	Intermediate Similarity	NPC474956
0.828	Intermediate Similarity	NPC30522
0.828	Intermediate Similarity	NPC477973
0.8265	Intermediate Similarity	NPC104861
0.8247	Intermediate Similarity	NPC89225
0.8247	Intermediate Similarity	NPC476768
0.8247	Intermediate Similarity	NPC26413
0.8235	Intermediate Similarity	NPC275539
0.8235	Intermediate Similarity	NPC189075
0.8229	Intermediate Similarity	NPC139459
0.8211	Intermediate Similarity	NPC298554
0.8211	Intermediate Similarity	NPC86368
0.8211	Intermediate Similarity	NPC63118
0.8211	Intermediate Similarity	NPC474436
0.8211	Intermediate Similarity	NPC49776
0.82	Intermediate Similarity	NPC179208
0.82	Intermediate Similarity	NPC36321
0.82	Intermediate Similarity	NPC478057
0.8191	Intermediate Similarity	NPC120968
0.8191	Intermediate Similarity	NPC290614
0.8191	Intermediate Similarity	NPC291028
0.8191	Intermediate Similarity	NPC210037
0.8191	Intermediate Similarity	NPC475965
0.8191	Intermediate Similarity	NPC273621
0.8191	Intermediate Similarity	NPC477872
0.8191	Intermediate Similarity	NPC227467
0.8191	Intermediate Similarity	NPC7260
0.8191	Intermediate Similarity	NPC152467
0.8191	Intermediate Similarity	NPC18872
0.8191	Intermediate Similarity	NPC474842
0.8182	Intermediate Similarity	NPC310981
0.8172	Intermediate Similarity	NPC246708
0.8172	Intermediate Similarity	NPC40552
0.8172	Intermediate Similarity	NPC182797
0.8172	Intermediate Similarity	NPC52169
0.8163	Intermediate Similarity	NPC58942
0.8163	Intermediate Similarity	NPC188833
0.8163	Intermediate Similarity	NPC176845
0.8163	Intermediate Similarity	NPC260149
0.8155	Intermediate Similarity	NPC112457
0.8152	Intermediate Similarity	NPC73038
0.8152	Intermediate Similarity	NPC325594
0.8144	Intermediate Similarity	NPC151725
0.8144	Intermediate Similarity	NPC111684
0.8144	Intermediate Similarity	NPC98874
0.8144	Intermediate Similarity	NPC106425
0.8144	Intermediate Similarity	NPC327179
0.8144	Intermediate Similarity	NPC122324
0.8144	Intermediate Similarity	NPC472806
0.8144	Intermediate Similarity	NPC58052
0.8144	Intermediate Similarity	NPC167193
0.8137	Intermediate Similarity	NPC110496
0.8132	Intermediate Similarity	NPC470812
0.8125	Intermediate Similarity	NPC272635
0.8125	Intermediate Similarity	NPC159410
0.8125	Intermediate Similarity	NPC78580
0.8125	Intermediate Similarity	NPC169751
0.8125	Intermediate Similarity	NPC222047
0.8125	Intermediate Similarity	NPC474529
0.8125	Intermediate Similarity	NPC184006
0.8125	Intermediate Similarity	NPC296164
0.8125	Intermediate Similarity	NPC23621
0.8125	Intermediate Similarity	NPC470697
0.8125	Intermediate Similarity	NPC209868
0.8111	Intermediate Similarity	NPC286786
0.8111	Intermediate Similarity	NPC163236
0.8111	Intermediate Similarity	NPC142683
0.8105	Intermediate Similarity	NPC105189
0.8105	Intermediate Similarity	NPC187722
0.81	Intermediate Similarity	NPC136289
0.8085	Intermediate Similarity	NPC270768
0.8085	Intermediate Similarity	NPC130520
0.8085	Intermediate Similarity	NPC470588
0.8085	Intermediate Similarity	NPC290972
0.8085	Intermediate Similarity	NPC225585
0.8085	Intermediate Similarity	NPC293048
0.8085	Intermediate Similarity	NPC127689
0.8085	Intermediate Similarity	NPC50070
0.8085	Intermediate Similarity	NPC59263
0.8085	Intermediate Similarity	NPC25906
0.8085	Intermediate Similarity	NPC64872
0.8085	Intermediate Similarity	NPC234346
0.8085	Intermediate Similarity	NPC61543
0.8085	Intermediate Similarity	NPC143232
0.8085	Intermediate Similarity	NPC198664
0.8085	Intermediate Similarity	NPC274330
0.8085	Intermediate Similarity	NPC184663
0.8085	Intermediate Similarity	NPC121798
0.8085	Intermediate Similarity	NPC263393
0.8081	Intermediate Similarity	NPC471041
0.8081	Intermediate Similarity	NPC470906
0.8065	Intermediate Similarity	NPC130577
0.8065	Intermediate Similarity	NPC142415
0.8065	Intermediate Similarity	NPC68160
0.8065	Intermediate Similarity	NPC242468
0.8065	Intermediate Similarity	NPC51700
0.8065	Intermediate Similarity	NPC171203
0.8065	Intermediate Similarity	NPC88716
0.8065	Intermediate Similarity	NPC307426
0.8065	Intermediate Similarity	NPC18064
0.8065	Intermediate Similarity	NPC102683
0.8065	Intermediate Similarity	NPC293564
0.8065	Intermediate Similarity	NPC98442
0.8061	Intermediate Similarity	NPC10057
0.8061	Intermediate Similarity	NPC84335
0.8061	Intermediate Similarity	NPC187933
0.8061	Intermediate Similarity	NPC38530
0.8061	Intermediate Similarity	NPC170131
0.8058	Intermediate Similarity	NPC476802
0.8058	Intermediate Similarity	NPC89171
0.8043	Intermediate Similarity	NPC474971
0.8041	Intermediate Similarity	NPC195715
0.8041	Intermediate Similarity	NPC473240
0.8041	Intermediate Similarity	NPC23241
0.8041	Intermediate Similarity	NPC148523
0.8041	Intermediate Similarity	NPC474727
0.8039	Intermediate Similarity	NPC1679
0.8022	Intermediate Similarity	NPC307258
0.8022	Intermediate Similarity	NPC132386
0.8021	Intermediate Similarity	NPC136313
0.8021	Intermediate Similarity	NPC229281
0.8021	Intermediate Similarity	NPC158059
0.8021	Intermediate Similarity	NPC307335
0.8021	Intermediate Similarity	NPC294263
0.8021	Intermediate Similarity	NPC476416
0.8021	Intermediate Similarity	NPC141497
0.8021	Intermediate Similarity	NPC74855
0.8021	Intermediate Similarity	NPC202728
0.8021	Intermediate Similarity	NPC118519
0.8021	Intermediate Similarity	NPC107674
0.8021	Intermediate Similarity	NPC170220
0.802	Intermediate Similarity	NPC95899
0.802	Intermediate Similarity	NPC264048
0.802	Intermediate Similarity	NPC275583
0.8	Intermediate Similarity	NPC195334
0.8	Intermediate Similarity	NPC111110
0.8	Intermediate Similarity	NPC470589

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 NPC269729 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	219
0.1-0.2	1826
0.2-0.3	3944
0.3-0.4	2068
0.4-0.5	683
0.5-0.6	191
0.6-0.7	147
0.7-0.8	65
0.8-0.85	4
0.85-0.9	3
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8913	High Similarity	NPD7900	Approved
0.8913	High Similarity	NPD7901	Clinical (unspecified phase)
0.8632	High Similarity	NPD7902	Approved
0.8511	High Similarity	NPD7748	Approved
0.8462	Intermediate Similarity	NPD3573	Approved
0.8298	Intermediate Similarity	NPD7515	Phase 2
0.8172	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7959	Intermediate Similarity	NPD4697	Phase 3
0.7957	Intermediate Similarity	NPD7521	Approved
0.7957	Intermediate Similarity	NPD7334	Approved
0.7957	Intermediate Similarity	NPD6409	Approved
0.7957	Intermediate Similarity	NPD6684	Approved
0.7957	Intermediate Similarity	NPD5330	Approved
0.7957	Intermediate Similarity	NPD7146	Approved
0.7835	Intermediate Similarity	NPD6399	Phase 3
0.783	Intermediate Similarity	NPD6649	Approved
0.783	Intermediate Similarity	NPD6650	Approved
0.781	Intermediate Similarity	NPD6373	Approved
0.781	Intermediate Similarity	NPD6372	Approved
0.7789	Intermediate Similarity	NPD6903	Approved
0.7789	Intermediate Similarity	NPD6672	Approved
0.7789	Intermediate Similarity	NPD5737	Approved
0.7732	Intermediate Similarity	NPD6079	Approved
0.7732	Intermediate Similarity	NPD8035	Phase 2
0.7732	Intermediate Similarity	NPD8034	Phase 2
0.7714	Intermediate Similarity	NPD6899	Approved
0.7714	Intermediate Similarity	NPD6881	Approved
0.7708	Intermediate Similarity	NPD5328	Approved
0.7692	Intermediate Similarity	NPD6675	Approved
0.7692	Intermediate Similarity	NPD6402	Approved
0.7692	Intermediate Similarity	NPD7128	Approved
0.7692	Intermediate Similarity	NPD6008	Approved
0.7692	Intermediate Similarity	NPD5739	Approved
0.7677	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD5697	Approved
0.7579	Intermediate Similarity	NPD3618	Phase 1
0.757	Intermediate Similarity	NPD7102	Approved
0.757	Intermediate Similarity	NPD7290	Approved
0.757	Intermediate Similarity	NPD6883	Approved
0.7547	Intermediate Similarity	NPD6011	Approved
0.7547	Intermediate Similarity	NPD7320	Approved
0.7527	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6869	Approved
0.75	Intermediate Similarity	NPD6847	Approved
0.75	Intermediate Similarity	NPD6617	Approved
0.75	Intermediate Similarity	NPD8130	Phase 1
0.7477	Intermediate Similarity	NPD6012	Approved
0.7477	Intermediate Similarity	NPD6014	Approved
0.7477	Intermediate Similarity	NPD6013	Approved
0.7474	Intermediate Similarity	NPD1694	Approved
0.7453	Intermediate Similarity	NPD5701	Approved
0.7451	Intermediate Similarity	NPD7638	Approved
0.7431	Intermediate Similarity	NPD6882	Approved
0.7431	Intermediate Similarity	NPD8297	Approved
0.7426	Intermediate Similarity	NPD7732	Phase 3
0.7426	Intermediate Similarity	NPD5221	Approved
0.7426	Intermediate Similarity	NPD5222	Approved
0.7426	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7379	Intermediate Similarity	NPD7639	Approved
0.7379	Intermediate Similarity	NPD7640	Approved
0.7353	Intermediate Similarity	NPD5173	Approved
0.7347	Intermediate Similarity	NPD6673	Approved
0.7347	Intermediate Similarity	NPD6080	Approved
0.7347	Intermediate Similarity	NPD6904	Approved
0.7339	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7292	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7232	Intermediate Similarity	NPD6868	Approved
0.7228	Intermediate Similarity	NPD6001	Approved
0.7212	Intermediate Similarity	NPD5286	Approved
0.7212	Intermediate Similarity	NPD4696	Approved
0.7212	Intermediate Similarity	NPD5285	Approved
0.72	Intermediate Similarity	NPD6411	Approved
0.7184	Intermediate Similarity	NPD6083	Phase 2
0.7184	Intermediate Similarity	NPD6084	Phase 2
0.7184	Intermediate Similarity	NPD4755	Approved
0.7172	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.7168	Intermediate Similarity	NPD7115	Discovery
0.7143	Intermediate Similarity	NPD5223	Approved
0.7115	Intermediate Similarity	NPD5696	Approved
0.7105	Intermediate Similarity	NPD6335	Approved
0.7094	Intermediate Similarity	NPD8328	Phase 3
0.7087	Intermediate Similarity	NPD7614	Phase 1
0.708	Intermediate Similarity	NPD6274	Approved
0.7075	Intermediate Similarity	NPD5211	Phase 2
0.7075	Intermediate Similarity	NPD4633	Approved
0.7075	Intermediate Similarity	NPD5225	Approved
0.7075	Intermediate Similarity	NPD5226	Approved
0.7075	Intermediate Similarity	NPD5224	Approved
0.7071	Intermediate Similarity	NPD5208	Approved
0.7054	Intermediate Similarity	NPD4632	Approved
0.7048	Intermediate Similarity	NPD4700	Approved
0.7043	Intermediate Similarity	NPD7100	Approved
0.7043	Intermediate Similarity	NPD7101	Approved
0.7041	Intermediate Similarity	NPD6098	Approved
0.7041	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD6050	Approved
0.703	Intermediate Similarity	NPD5693	Phase 1
0.7021	Intermediate Similarity	NPD7645	Phase 2
0.7018	Intermediate Similarity	NPD6317	Approved
0.701	Intermediate Similarity	NPD3133	Approved
0.701	Intermediate Similarity	NPD3665	Phase 1
0.701	Intermediate Similarity	NPD3666	Approved
0.701	Intermediate Similarity	NPD4786	Approved
0.701	Intermediate Similarity	NPD3668	Phase 3
0.7009	Intermediate Similarity	NPD5175	Approved
0.7009	Intermediate Similarity	NPD5174	Approved
0.7	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD6101	Approved
0.699	Remote Similarity	NPD5695	Phase 3
0.6979	Remote Similarity	NPD3667	Approved
0.6975	Remote Similarity	NPD7507	Approved
0.6972	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6961	Remote Similarity	NPD4202	Approved
0.6957	Remote Similarity	NPD6314	Approved
0.6957	Remote Similarity	NPD6313	Approved
0.6952	Remote Similarity	NPD4225	Approved
0.6947	Remote Similarity	NPD4695	Discontinued
0.6944	Remote Similarity	NPD5141	Approved
0.6931	Remote Similarity	NPD5692	Phase 3
0.6931	Remote Similarity	NPD5207	Approved
0.6923	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.687	Remote Similarity	NPD6009	Approved
0.6863	Remote Similarity	NPD5694	Approved
0.686	Remote Similarity	NPD7736	Approved
0.6852	Remote Similarity	NPD4754	Approved
0.6847	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6838	Remote Similarity	NPD6319	Approved
0.6807	Remote Similarity	NPD7604	Phase 2
0.6803	Remote Similarity	NPD7319	Approved
0.6786	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.678	Remote Similarity	NPD6909	Approved
0.678	Remote Similarity	NPD6908	Approved
0.678	Remote Similarity	NPD5983	Phase 2
0.6759	Remote Similarity	NPD7632	Discontinued
0.6757	Remote Similarity	NPD5128	Approved
0.6757	Remote Similarity	NPD5168	Approved
0.6757	Remote Similarity	NPD4730	Approved
0.6757	Remote Similarity	NPD4729	Approved
0.675	Remote Similarity	NPD7492	Approved
0.6727	Remote Similarity	NPD4768	Approved
0.6727	Remote Similarity	NPD4767	Approved
0.6724	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6703	Remote Similarity	NPD4691	Approved
0.6699	Remote Similarity	NPD5281	Approved
0.6699	Remote Similarity	NPD5284	Approved
0.6697	Remote Similarity	NPD6052	Approved
0.6695	Remote Similarity	NPD6054	Approved
0.6694	Remote Similarity	NPD6616	Approved
0.6694	Remote Similarity	NPD6336	Discontinued
0.6667	Remote Similarity	NPD4753	Phase 2
0.6667	Remote Similarity	NPD6412	Phase 2
0.6667	Remote Similarity	NPD4629	Approved
0.6667	Remote Similarity	NPD5210	Approved
0.6667	Remote Similarity	NPD6614	Approved
0.6667	Remote Similarity	NPD6051	Approved
0.6639	Remote Similarity	NPD7078	Approved
0.6637	Remote Similarity	NPD5135	Approved
0.6637	Remote Similarity	NPD5247	Approved
0.6637	Remote Similarity	NPD5250	Approved
0.6637	Remote Similarity	NPD4634	Approved
0.6637	Remote Similarity	NPD5248	Approved
0.6637	Remote Similarity	NPD5169	Approved
0.6637	Remote Similarity	NPD5251	Approved
0.6637	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6637	Remote Similarity	NPD5249	Phase 3
0.6635	Remote Similarity	NPD5778	Approved
0.6635	Remote Similarity	NPD5779	Approved
0.6633	Remote Similarity	NPD4223	Phase 3
0.6633	Remote Similarity	NPD4221	Approved
0.6609	Remote Similarity	NPD7094	Approved
0.6609	Remote Similarity	NPD6858	Approved
0.6607	Remote Similarity	NPD6686	Approved
0.66	Remote Similarity	NPD5329	Approved
0.6598	Remote Similarity	NPD7525	Registered
0.6593	Remote Similarity	NPD4137	Phase 3
0.6583	Remote Similarity	NPD6370	Approved
0.6579	Remote Similarity	NPD5215	Approved
0.6579	Remote Similarity	NPD5127	Approved
0.6579	Remote Similarity	NPD5216	Approved
0.6579	Remote Similarity	NPD5217	Approved
0.6555	Remote Similarity	NPD6059	Approved
0.6549	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6535	Remote Similarity	NPD5279	Phase 3
0.6526	Remote Similarity	NPD6117	Approved
0.6522	Remote Similarity	NPD4747	Approved
0.6509	Remote Similarity	NPD5654	Approved
0.6504	Remote Similarity	NPD8293	Discontinued
0.65	Remote Similarity	NPD6016	Approved
0.65	Remote Similarity	NPD4197	Approved
0.65	Remote Similarity	NPD6015	Approved
0.6489	Remote Similarity	NPD4058	Approved
0.646	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6458	Remote Similarity	NPD6116	Phase 1
0.6452	Remote Similarity	NPD5777	Approved
0.6449	Remote Similarity	NPD5349	Clinical (unspecified phase)
0.6446	Remote Similarity	NPD5988	Approved
0.6421	Remote Similarity	NPD8039	Approved
0.641	Remote Similarity	NPD5167	Approved
0.64	Remote Similarity	NPD4788	Approved
0.6392	Remote Similarity	NPD6115	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