NPASS Compound

Structure

NPC470980 OpenBabel07101718292D 37 39 0 0 1 0 0 0 0 0999 V2000 1.8320 6.7588 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.4004 -1.6899 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0999 4.7588 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4004 -3.4219 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4300 2.2588 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5458 -2.4135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8985 -2.9488 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6140 -0.5027 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9659 6.2588 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9004 -2.5559 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8320 4.7588 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2588 0.9659 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9659 5.2588 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9004 -2.5559 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 3.5640 1.7588 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2368 -1.4625 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.5895 -1.9977 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8320 3.7588 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5640 0.7588 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.9059 -0.7193 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.6980 0.2588 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.8320 0.7588 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.3071 0.0897 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.8320 1.7588 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.6980 2.2588 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.9004 -0.8239 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.4004 -1.6899 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9659 0.2588 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.3887 -1.7898 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9659 3.2588 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.2853 0.2976 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9659 2.2588 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.9004 -0.8239 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 1.2586 -1.2546 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6980 3.2588 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.4004 -1.6899 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 9 1 0 0 0 0 2 10 1 0 0 0 0 3 13 1 0 0 0 0 4 14 1 0 0 0 0 5 15 2 0 0 0 0 7 17 1 0 0 0 0 8 28 1 0 0 0 0 9 13 1 0 0 0 0 10 14 1 0 0 0 0 11 13 2 0 0 0 0 11 18 1 0 0 0 0 12 28 1 0 0 0 0 12 34 1 0 0 0 0 14 27 1 0 0 0 0 15 25 1 0 0 0 0 16 6 1 6 0 0 0 16 35 1 0 0 0 0 17 29 2 0 0 0 0 17 35 1 0 0 0 0 18 30 2 0 0 0 0 18 36 1 0 0 0 0 19 15 1 6 0 0 0 19 21 1 0 0 0 0 19 23 1 0 0 0 0 20 16 1 6 0 0 0 20 21 1 0 0 0 0 20 26 1 0 0 0 0 21 22 1 0 0 0 0 22 24 1 0 0 0 0 22 28 1 0 0 0 0 23 26 1 0 0 0 0 23 31 1 0 0 0 0 24 25 1 0 0 0 0 24 32 1 0 0 0 0 25 36 1 0 0 0 0 26 37 1 0 0 0 0 27 33 2 0 0 0 0 27 37 1 0 0 0 0 28 34 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	416.18
Volume:	429.691
LogP:	4.868
LogD:	2.142
LogS:	-3.766
# Rotatable Bonds:	7
TPSA:	117.2
# H-Bond Aceptor:	7
# H-Bond Donor:	3
# Rings:	2
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.462
Synthetic Accessibility Score:	3.378
Fsp3:	0.391
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:	-4.831
MDCK Permeability:	1.572620021761395e-05
Pgp-inhibitor:	0.674
Pgp-substrate:	0.863
Human Intestinal Absorption (HIA):	0.19
20% Bioavailability (F20%):	0.139
30% Bioavailability (F30%):	0.004

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.004
Plasma Protein Binding (PPB):	96.3925552368164%
Volume Distribution (VD):	0.48
Pgp-substrate:	4.037344455718994%

ADMET: Metabolism

CYP1A2-inhibitor:	0.245
CYP1A2-substrate:	0.936
CYP2C19-inhibitor:	0.484
CYP2C19-substrate:	0.198
CYP2C9-inhibitor:	0.836
CYP2C9-substrate:	0.847
CYP2D6-inhibitor:	0.146
CYP2D6-substrate:	0.214
CYP3A4-inhibitor:	0.262
CYP3A4-substrate:	0.231

ADMET: Excretion

Clearance (CL):	3.239
Half-life (T1/2):	0.32

ADMET: Toxicity

hERG Blockers:	0.002
Human Hepatotoxicity (H-HT):	0.969
Drug-inuced Liver Injury (DILI):	0.978
AMES Toxicity:	0.022
Rat Oral Acute Toxicity:	0.247
Maximum Recommended Daily Dose:	0.019
Skin Sensitization:	0.839
Carcinogencity:	0.111
Eye Corrosion:	0.003
Eye Irritation:	0.168
Respiratory Toxicity:	0.373

Download Data

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

Natural Product: NPC470980

Natural Product ID:	NPC470980
*Common Name:**	Songaricalarin A
IUPAC Name:	[(1S,2R,3S,3aR,5S,6R,7S,7aS)-1-[(1S)-1-acetyloxyethyl]-3,6-dihydroxy-2-(2-methylbutanoyloxy)-4-methylidene-7-[(2S)-2-methyloxiran-2-yl]-1,2,3,3a,5,6,7,7a-octahydroinden-5-yl] (E)-3-methylpent-2-enoate
Synonyms:	Songaricalarin A
Standard InCHIKey:	ABZABIRGUJABNL-BBQIEXHJSA-N
Standard InCHI:	InChI=1S/C28H42O9/c1-9-13(3)11-18(30)36-25-15(5)19-21(22(24(25)32)28(8)12-34-28)20(16(6)35-17(7)29)26(23(19)31)37-27(33)14(4)10-2/h11,14,16,19-26,31-32H,5,9-10,12H2,1-4,6-8H3/b13-11+/t14?,16-,19-,20+,21-,22-,23-,24+,25-,26+,28+/m0/s1
SMILES:	CCC(C)C(=O)OC1C(C2C(C1O)C(=C)C(C(C2C3(CO3)C)O)OC(=O)C=C(C)CC)C(C)OC(=O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2334779
PubChem CID:	71717008
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001550] Sesquiterpenoids

*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
NPO5813	Ligularia songarica	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23043462]
NPO5813	Ligularia songarica	Species	Asteraceae	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
EC50	4

Activity Type	# Activity
Cell Line	3
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	EC50	>	20.0	ug.mL-1	PMID[523500]
NPT83	Cell Line	MCF7	Homo sapiens	EC50	=	10.4	ug.mL-1	PMID[523500]
NPT91	Cell Line	KB	Homo sapiens	EC50	=	17.4	ug.mL-1	PMID[523500]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	EC50	=	10.4	ug.mL-1	PMID[523500]

☑ 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 NPC470980 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	206
0.1-0.2	1293
0.2-0.3	4455
0.3-0.4	8512
0.4-0.5	13365
0.5-0.6	7118
0.6-0.7	5951
0.7-0.8	1688
0.8-0.85	95
0.85-0.9	11
0.9-0.95	0
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9691	High Similarity	NPC470972
0.8835	High Similarity	NPC475290
0.8738	High Similarity	NPC473577
0.8738	High Similarity	NPC475585
0.8738	High Similarity	NPC474550
0.8558	High Similarity	NPC103298
0.8558	High Similarity	NPC288502
0.8558	High Similarity	NPC181104
0.8558	High Similarity	NPC475331
0.8558	High Similarity	NPC475335
0.8558	High Similarity	NPC121518
0.8558	High Similarity	NPC201144
0.8558	High Similarity	NPC80809
0.8532	High Similarity	NPC216665
0.8476	Intermediate Similarity	NPC470975
0.8476	Intermediate Similarity	NPC60315
0.8476	Intermediate Similarity	NPC470979
0.8476	Intermediate Similarity	NPC103088
0.8462	Intermediate Similarity	NPC473694
0.8462	Intermediate Similarity	NPC475623
0.8462	Intermediate Similarity	NPC475334
0.8411	Intermediate Similarity	NPC471934
0.8393	Intermediate Similarity	NPC472667
0.8365	Intermediate Similarity	NPC472552
0.8365	Intermediate Similarity	NPC214714
0.8365	Intermediate Similarity	NPC200672
0.8364	Intermediate Similarity	NPC43213
0.835	Intermediate Similarity	NPC272223
0.8349	Intermediate Similarity	NPC471933
0.8333	Intermediate Similarity	NPC472998
0.8318	Intermediate Similarity	NPC88701
0.8317	Intermediate Similarity	NPC469583
0.8302	Intermediate Similarity	NPC186668
0.8286	Intermediate Similarity	NPC474124
0.8269	Intermediate Similarity	NPC475617
0.8269	Intermediate Similarity	NPC472554
0.8269	Intermediate Similarity	NPC26557
0.8257	Intermediate Similarity	NPC470076
0.8235	Intermediate Similarity	NPC472996
0.8235	Intermediate Similarity	NPC472995
0.8235	Intermediate Similarity	NPC472997
0.823	Intermediate Similarity	NPC278681
0.822	Intermediate Similarity	NPC475371
0.8208	Intermediate Similarity	NPC473543
0.82	Intermediate Similarity	NPC122057
0.8198	Intermediate Similarity	NPC178289
0.819	Intermediate Similarity	NPC252242
0.819	Intermediate Similarity	NPC475344
0.819	Intermediate Similarity	NPC476471
0.819	Intermediate Similarity	NPC475956
0.8165	Intermediate Similarity	NPC472215
0.8165	Intermediate Similarity	NPC472214
0.8158	Intermediate Similarity	NPC112936
0.8158	Intermediate Similarity	NPC143755
0.8148	Intermediate Similarity	NPC181994
0.8142	Intermediate Similarity	NPC16701
0.8137	Intermediate Similarity	NPC329435
0.8131	Intermediate Similarity	NPC119855
0.8131	Intermediate Similarity	NPC220217
0.8125	Intermediate Similarity	NPC470793
0.8125	Intermediate Similarity	NPC470075
0.8113	Intermediate Similarity	NPC474783
0.8113	Intermediate Similarity	NPC472821
0.8113	Intermediate Similarity	NPC473523
0.8113	Intermediate Similarity	NPC260809
0.8113	Intermediate Similarity	NPC232515
0.8087	Intermediate Similarity	NPC310511
0.8087	Intermediate Similarity	NPC312481
0.8077	Intermediate Similarity	NPC474957
0.8077	Intermediate Similarity	NPC79449
0.8073	Intermediate Similarity	NPC257853
0.807	Intermediate Similarity	NPC213761
0.807	Intermediate Similarity	NPC35171
0.807	Intermediate Similarity	NPC475041
0.8053	Intermediate Similarity	NPC185287
0.8053	Intermediate Similarity	NPC157380
0.8053	Intermediate Similarity	NPC290693
0.8053	Intermediate Similarity	NPC203862
0.8053	Intermediate Similarity	NPC152615
0.8036	Intermediate Similarity	NPC305044
0.8036	Intermediate Similarity	NPC265290
0.8019	Intermediate Similarity	NPC475986
0.8019	Intermediate Similarity	NPC475038
0.8019	Intermediate Similarity	NPC109195
0.8017	Intermediate Similarity	NPC115349
0.8017	Intermediate Similarity	NPC470265
0.8017	Intermediate Similarity	NPC269642
0.8017	Intermediate Similarity	NPC23786
0.8	Intermediate Similarity	NPC38855
0.8	Intermediate Similarity	NPC473510
0.8	Intermediate Similarity	NPC230546
0.8	Intermediate Similarity	NPC79579
0.8	Intermediate Similarity	NPC472004
0.7983	Intermediate Similarity	NPC470850
0.7982	Intermediate Similarity	NPC469916
0.7982	Intermediate Similarity	NPC94377
0.7982	Intermediate Similarity	NPC472439
0.7981	Intermediate Similarity	NPC210337
0.7981	Intermediate Similarity	NPC476057
0.7981	Intermediate Similarity	NPC347923
0.7981	Intermediate Similarity	NPC205143
0.7981	Intermediate Similarity	NPC475033
0.7981	Intermediate Similarity	NPC254121
0.7981	Intermediate Similarity	NPC475032
0.7966	Intermediate Similarity	NPC470973
0.7965	Intermediate Similarity	NPC199428
0.7965	Intermediate Similarity	NPC106228
0.7965	Intermediate Similarity	NPC5311
0.7965	Intermediate Similarity	NPC138372
0.7965	Intermediate Similarity	NPC193382
0.7965	Intermediate Similarity	NPC99620
0.7965	Intermediate Similarity	NPC310341
0.7963	Intermediate Similarity	NPC469960
0.7963	Intermediate Similarity	NPC93026
0.7963	Intermediate Similarity	NPC265502
0.7963	Intermediate Similarity	NPC29389
0.7961	Intermediate Similarity	NPC220221
0.7949	Intermediate Similarity	NPC473802
0.7949	Intermediate Similarity	NPC6193
0.7949	Intermediate Similarity	NPC129992
0.7946	Intermediate Similarity	NPC101400
0.7946	Intermediate Similarity	NPC962
0.7946	Intermediate Similarity	NPC101965
0.7946	Intermediate Similarity	NPC317210
0.7946	Intermediate Similarity	NPC250109
0.7944	Intermediate Similarity	NPC196471
0.7944	Intermediate Similarity	NPC10232
0.7944	Intermediate Similarity	NPC160583
0.7944	Intermediate Similarity	NPC187302
0.7944	Intermediate Similarity	NPC23584
0.7944	Intermediate Similarity	NPC189588
0.7944	Intermediate Similarity	NPC97487
0.7931	Intermediate Similarity	NPC233500
0.7931	Intermediate Similarity	NPC67569
0.7928	Intermediate Similarity	NPC71680
0.7925	Intermediate Similarity	NPC222875
0.7925	Intermediate Similarity	NPC268829
0.7925	Intermediate Similarity	NPC25177
0.7925	Intermediate Similarity	NPC247701
0.7925	Intermediate Similarity	NPC295110
0.7925	Intermediate Similarity	NPC11974
0.7921	Intermediate Similarity	NPC471378
0.7921	Intermediate Similarity	NPC312471
0.7917	Intermediate Similarity	NPC104382
0.7913	Intermediate Similarity	NPC44899
0.7913	Intermediate Similarity	NPC329905
0.7913	Intermediate Similarity	NPC9674
0.7913	Intermediate Similarity	NPC19028
0.7913	Intermediate Similarity	NPC304260
0.7913	Intermediate Similarity	NPC5883
0.7913	Intermediate Similarity	NPC29639
0.7913	Intermediate Similarity	NPC219656
0.7913	Intermediate Similarity	NPC5292
0.7909	Intermediate Similarity	NPC472216
0.7909	Intermediate Similarity	NPC5475
0.7909	Intermediate Similarity	NPC284828
0.7909	Intermediate Similarity	NPC173905
0.7905	Intermediate Similarity	NPC222303
0.7905	Intermediate Similarity	NPC471932
0.7905	Intermediate Similarity	NPC274458
0.7895	Intermediate Similarity	NPC158344
0.7895	Intermediate Similarity	NPC77319
0.7895	Intermediate Similarity	NPC309034
0.7895	Intermediate Similarity	NPC473852
0.7895	Intermediate Similarity	NPC196429
0.7895	Intermediate Similarity	NPC244402
0.7895	Intermediate Similarity	NPC142066
0.7895	Intermediate Similarity	NPC243196
0.7895	Intermediate Similarity	NPC93883
0.7895	Intermediate Similarity	NPC471353
0.7895	Intermediate Similarity	NPC471355
0.7895	Intermediate Similarity	NPC474418
0.7895	Intermediate Similarity	NPC157376
0.7895	Intermediate Similarity	NPC99728
0.7895	Intermediate Similarity	NPC87250
0.7895	Intermediate Similarity	NPC50305
0.7895	Intermediate Similarity	NPC471354
0.7895	Intermediate Similarity	NPC27507
0.7895	Intermediate Similarity	NPC84987
0.7895	Intermediate Similarity	NPC34390
0.7895	Intermediate Similarity	NPC471351
0.789	Intermediate Similarity	NPC473586
0.789	Intermediate Similarity	NPC472820
0.789	Intermediate Similarity	NPC469959
0.789	Intermediate Similarity	NPC187435
0.789	Intermediate Similarity	NPC472263
0.789	Intermediate Similarity	NPC469957
0.789	Intermediate Similarity	NPC67321
0.789	Intermediate Similarity	NPC108682
0.7885	Intermediate Similarity	NPC88009
0.7885	Intermediate Similarity	NPC475304
0.7881	Intermediate Similarity	NPC469790
0.7881	Intermediate Similarity	NPC473919
0.7881	Intermediate Similarity	NPC8374
0.7881	Intermediate Similarity	NPC473709
0.7876	Intermediate Similarity	NPC471633
0.7876	Intermediate Similarity	NPC84949
0.7876	Intermediate Similarity	NPC31354
0.7876	Intermediate Similarity	NPC69576
0.787	Intermediate Similarity	NPC161775

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 NPC470980 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	172
0.1-0.2	1641
0.2-0.3	3849
0.3-0.4	2363
0.4-0.5	672
0.5-0.6	258
0.6-0.7	165
0.7-0.8	30
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
0.8269	Intermediate Similarity	NPD5344	Discontinued
0.7921	Intermediate Similarity	NPD6698	Approved
0.7921	Intermediate Similarity	NPD46	Approved
0.7913	Intermediate Similarity	NPD7516	Approved
0.7905	Intermediate Similarity	NPD7638	Approved
0.783	Intermediate Similarity	NPD7639	Approved
0.783	Intermediate Similarity	NPD6648	Approved
0.783	Intermediate Similarity	NPD7640	Approved
0.7826	Intermediate Similarity	NPD7327	Approved
0.7826	Intermediate Similarity	NPD7328	Approved
0.7778	Intermediate Similarity	NPD8033	Approved
0.7745	Intermediate Similarity	NPD7838	Discovery
0.7692	Intermediate Similarity	NPD8377	Approved
0.7692	Intermediate Similarity	NPD8294	Approved
0.7667	Intermediate Similarity	NPD7507	Approved
0.7627	Intermediate Similarity	NPD8380	Approved
0.7627	Intermediate Similarity	NPD8379	Approved
0.7627	Intermediate Similarity	NPD8378	Approved
0.7627	Intermediate Similarity	NPD8296	Approved
0.7627	Intermediate Similarity	NPD8335	Approved
0.7589	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7586	Intermediate Similarity	NPD7115	Discovery
0.757	Intermediate Similarity	NPD4225	Approved
0.748	Intermediate Similarity	NPD7319	Approved
0.7479	Intermediate Similarity	NPD7503	Approved
0.7411	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7395	Intermediate Similarity	NPD6319	Approved
0.7391	Intermediate Similarity	NPD6053	Discontinued
0.7368	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD6371	Approved
0.7345	Intermediate Similarity	NPD6686	Approved
0.7241	Intermediate Similarity	NPD8297	Approved
0.7207	Intermediate Similarity	NPD7632	Discontinued
0.7179	Intermediate Similarity	NPD4632	Approved
0.7168	Intermediate Similarity	NPD5739	Approved
0.7168	Intermediate Similarity	NPD6008	Approved
0.7168	Intermediate Similarity	NPD6675	Approved
0.7168	Intermediate Similarity	NPD6402	Approved
0.7168	Intermediate Similarity	NPD7128	Approved
0.713	Intermediate Similarity	NPD6373	Approved
0.713	Intermediate Similarity	NPD6372	Approved
0.7105	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.7087	Intermediate Similarity	NPD6082	Clinical (unspecified phase)
0.7043	Intermediate Similarity	NPD7320	Approved
0.7043	Intermediate Similarity	NPD6881	Approved
0.7043	Intermediate Similarity	NPD6899	Approved
0.7016	Intermediate Similarity	NPD7492	Approved
0.7009	Intermediate Similarity	NPD6649	Approved
0.7009	Intermediate Similarity	NPD6650	Approved
0.6967	Remote Similarity	NPD6059	Approved
0.6967	Remote Similarity	NPD6054	Approved
0.696	Remote Similarity	NPD6616	Approved
0.6957	Remote Similarity	NPD5701	Approved
0.6957	Remote Similarity	NPD5697	Approved
0.6957	Remote Similarity	NPD6412	Phase 2
0.6952	Remote Similarity	NPD7524	Approved
0.6952	Remote Similarity	NPD4250	Approved
0.6952	Remote Similarity	NPD4251	Approved
0.6949	Remote Similarity	NPD6882	Approved
0.6937	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6935	Remote Similarity	NPD7604	Phase 2
0.6931	Remote Similarity	NPD4819	Approved
0.6931	Remote Similarity	NPD4822	Approved
0.6931	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6931	Remote Similarity	NPD4821	Approved
0.6931	Remote Similarity	NPD4820	Approved
0.6923	Remote Similarity	NPD7102	Approved
0.6923	Remote Similarity	NPD6883	Approved
0.6923	Remote Similarity	NPD7290	Approved
0.6905	Remote Similarity	NPD8293	Discontinued
0.6905	Remote Similarity	NPD7078	Approved
0.6891	Remote Similarity	NPD8133	Approved
0.6864	Remote Similarity	NPD6847	Approved
0.6864	Remote Similarity	NPD8130	Phase 1
0.6864	Remote Similarity	NPD6617	Approved
0.6864	Remote Similarity	NPD6869	Approved
0.686	Remote Similarity	NPD6009	Approved
0.6857	Remote Similarity	NPD4249	Approved
0.6855	Remote Similarity	NPD6370	Approved
0.6852	Remote Similarity	NPD7637	Suspended
0.685	Remote Similarity	NPD7736	Approved
0.6847	Remote Similarity	NPD6083	Phase 2
0.6847	Remote Similarity	NPD6084	Phase 2
0.6838	Remote Similarity	NPD6014	Approved
0.6838	Remote Similarity	NPD6012	Approved
0.6838	Remote Similarity	NPD6013	Approved
0.6822	Remote Similarity	NPD1695	Approved
0.678	Remote Similarity	NPD4634	Approved
0.6774	Remote Similarity	NPD5983	Phase 2
0.6774	Remote Similarity	NPD6016	Approved
0.6774	Remote Similarity	NPD6015	Approved
0.6752	Remote Similarity	NPD6011	Approved
0.6733	Remote Similarity	NPD4271	Approved
0.6733	Remote Similarity	NPD4268	Approved
0.6731	Remote Similarity	NPD5362	Discontinued
0.6723	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.672	Remote Similarity	NPD5988	Approved
0.6697	Remote Similarity	NPD7983	Approved
0.6696	Remote Similarity	NPD4755	Approved
0.6693	Remote Similarity	NPD6336	Discontinued
0.6667	Remote Similarity	NPD5695	Phase 3
0.6667	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4159	Approved
0.6667	Remote Similarity	NPD6051	Approved
0.6636	Remote Similarity	NPD6399	Phase 3
0.6636	Remote Similarity	NPD4202	Approved
0.661	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6609	Remote Similarity	NPD5211	Phase 2
0.6607	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.6606	Remote Similarity	NPD5785	Approved
0.6606	Remote Similarity	NPD3168	Discontinued
0.6583	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6579	Remote Similarity	NPD5286	Approved
0.6579	Remote Similarity	NPD4700	Approved
0.6579	Remote Similarity	NPD5285	Approved
0.6579	Remote Similarity	NPD4696	Approved
0.6571	Remote Similarity	NPD6695	Phase 3
0.6571	Remote Similarity	NPD5331	Approved
0.6571	Remote Similarity	NPD5332	Approved
0.6538	Remote Similarity	NPD4790	Discontinued
0.6518	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6508	Remote Similarity	NPD8513	Phase 3
0.6508	Remote Similarity	NPD8515	Approved
0.6508	Remote Similarity	NPD8517	Approved
0.6508	Remote Similarity	NPD8516	Approved
0.6504	Remote Similarity	NPD6274	Approved
0.6496	Remote Similarity	NPD5141	Approved
0.6491	Remote Similarity	NPD5696	Approved
0.6486	Remote Similarity	NPD5778	Approved
0.6486	Remote Similarity	NPD5779	Approved
0.648	Remote Similarity	NPD7100	Approved
0.648	Remote Similarity	NPD7101	Approved
0.6476	Remote Similarity	NPD6435	Approved
0.6466	Remote Similarity	NPD5225	Approved
0.6466	Remote Similarity	NPD5224	Approved
0.6466	Remote Similarity	NPD4633	Approved
0.6466	Remote Similarity	NPD5226	Approved
0.6462	Remote Similarity	NPD6033	Approved
0.6449	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6449	Remote Similarity	NPD5363	Approved
0.6442	Remote Similarity	NPD7525	Registered
0.6441	Remote Similarity	NPD4768	Approved
0.6441	Remote Similarity	NPD4767	Approved
0.6417	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6415	Remote Similarity	NPD7154	Phase 3
0.641	Remote Similarity	NPD5175	Approved
0.641	Remote Similarity	NPD5174	Approved
0.6406	Remote Similarity	NPD6067	Discontinued
0.64	Remote Similarity	NPD6335	Approved
0.6396	Remote Similarity	NPD5693	Phase 1
0.6389	Remote Similarity	NPD7521	Approved
0.6389	Remote Similarity	NPD6684	Approved
0.6389	Remote Similarity	NPD6409	Approved
0.6389	Remote Similarity	NPD7334	Approved
0.6389	Remote Similarity	NPD7146	Approved
0.6389	Remote Similarity	NPD5330	Approved
0.6383	Remote Similarity	NPD7625	Phase 1
0.6381	Remote Similarity	NPD5369	Approved
0.6379	Remote Similarity	NPD5223	Approved
0.6378	Remote Similarity	NPD6908	Approved
0.6378	Remote Similarity	NPD6909	Approved
0.6364	Remote Similarity	NPD4753	Phase 2
0.6364	Remote Similarity	NPD5328	Approved
0.6333	Remote Similarity	NPD4730	Approved
0.6333	Remote Similarity	NPD4729	Approved
0.633	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.633	Remote Similarity	NPD7750	Discontinued
0.6325	Remote Similarity	NPD3653	Clinical (unspecified phase)
0.6321	Remote Similarity	NPD4270	Approved
0.6321	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6321	Remote Similarity	NPD4269	Approved
0.632	Remote Similarity	NPD6317	Approved
0.6286	Remote Similarity	NPD6931	Approved
0.6286	Remote Similarity	NPD6930	Phase 2
0.6286	Remote Similarity	NPD5368	Approved
0.6283	Remote Similarity	NPD7748	Approved
0.6279	Remote Similarity	NPD8328	Phase 3
0.6273	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6273	Remote Similarity	NPD6903	Approved
0.6271	Remote Similarity	NPD4754	Approved
0.627	Remote Similarity	NPD6313	Approved
0.627	Remote Similarity	NPD6314	Approved
0.6261	Remote Similarity	NPD7902	Approved
0.626	Remote Similarity	NPD8074	Phase 3
0.625	Remote Similarity	NPD6079	Approved
0.625	Remote Similarity	NPD7515	Phase 2
0.625	Remote Similarity	NPD5284	Approved
0.625	Remote Similarity	NPD8035	Phase 2
0.625	Remote Similarity	NPD8034	Phase 2
0.625	Remote Similarity	NPD5281	Approved
0.6239	Remote Similarity	NPD5786	Approved
0.6239	Remote Similarity	NPD3618	Phase 1
0.623	Remote Similarity	NPD5251	Approved
0.623	Remote Similarity	NPD5250	Approved
0.623	Remote Similarity	NPD5247	Approved
0.623	Remote Similarity	NPD5248	Approved
0.623	Remote Similarity	NPD5249	Phase 3
0.6216	Remote Similarity	NPD6673	Approved
0.6216	Remote Similarity	NPD6904	Approved
0.6216	Remote Similarity	NPD6080	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