NPASS Compound

Structure

NPC470972 OpenBabel07101718312D 33 35 0 0 1 0 0 0 0 0999 V2000 -6.9282 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -5.0000 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 -1.1587 1.0134 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7986 2.7076 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8005 0.5827 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 -6.0622 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2072 -0.3309 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 -5.1962 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1369 1.2213 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7767 2.9155 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3005 1.4487 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.8005 0.5827 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.4641 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8060 0.4781 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5981 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 0.0000 C 0 0 2 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 -0.8660 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.0858 3.8666 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.8005 2.3147 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -5.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4459 2.1723 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3005 1.4487 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 8 1 0 0 0 0 2 12 1 0 0 0 0 3 13 2 0 0 0 0 5 15 1 0 0 0 0 6 16 1 0 0 0 0 7 25 1 0 0 0 0 8 12 1 0 0 0 0 9 12 2 0 0 0 0 9 19 1 0 0 0 0 10 18 1 0 0 0 0 11 25 1 0 0 0 0 11 30 1 0 0 0 0 13 17 1 0 0 0 0 13 24 1 0 0 0 0 14 4 1 1 0 0 0 14 31 1 0 0 0 0 15 26 2 0 0 0 0 15 31 1 0 0 0 0 16 27 2 0 0 0 0 16 32 1 0 0 0 0 17 10 1 6 0 0 0 17 21 1 0 0 0 0 18 20 1 0 0 0 0 18 32 1 6 0 0 0 19 28 2 0 0 0 0 19 33 1 0 0 0 0 20 14 1 6 0 0 0 20 21 1 0 0 0 0 21 22 1 0 0 0 0 22 23 1 0 0 0 0 22 25 1 0 0 0 0 23 24 1 0 0 0 0 23 29 1 0 0 0 0 24 33 1 0 0 0 0 25 30 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	596.28
Volume:	597.567
LogP:	4.303
LogD:	2.275
LogS:	-4.317
# Rotatable Bonds:	14
TPSA:	128.73
# H-Bond Aceptor:	9
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	10

MedChem Properties

QED Drug-Likeness Score:	0.122
Synthetic Accessibility Score:	5.568
Fsp3:	0.742
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	2
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.935
MDCK Permeability:	8.494124631397426e-05
Pgp-inhibitor:	1.0
Pgp-substrate:	0.004
Human Intestinal Absorption (HIA):	0.026
20% Bioavailability (F20%):	0.937
30% Bioavailability (F30%):	0.952

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.596
Plasma Protein Binding (PPB):	92.7755355834961%
Volume Distribution (VD):	2.109
Pgp-substrate:	6.101034641265869%

ADMET: Metabolism

CYP1A2-inhibitor:	0.156
CYP1A2-substrate:	0.57
CYP2C19-inhibitor:	0.769
CYP2C19-substrate:	0.607
CYP2C9-inhibitor:	0.883
CYP2C9-substrate:	0.012
CYP2D6-inhibitor:	0.023
CYP2D6-substrate:	0.035
CYP3A4-inhibitor:	0.922
CYP3A4-substrate:	0.544

ADMET: Excretion

Clearance (CL):	7.07
Half-life (T1/2):	0.308

ADMET: Toxicity

hERG Blockers:	0.147
Human Hepatotoxicity (H-HT):	0.952
Drug-inuced Liver Injury (DILI):	0.765
AMES Toxicity:	0.051
Rat Oral Acute Toxicity:	0.195
Maximum Recommended Daily Dose:	0.342
Skin Sensitization:	0.575
Carcinogencity:	0.082
Eye Corrosion:	0.007
Eye Irritation:	0.011
Respiratory Toxicity:	0.915

Download Data

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

Natural Product: NPC470972

Natural Product ID:	NPC470972
*Common Name:**	Songaricalarin B
IUPAC Name:	[(1S,2S,3aR,5S,6R,7S,7aS)-2-acetyloxy-1-[(1S)-1-acetyloxyethyl]-6-hydroxy-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 B
Standard InCHIKey:	QDBZIKDKBOCSPO-QFKYJAFMSA-N
Standard InCHI:	InChI=1S/C25H36O8/c1-8-12(2)9-19(28)33-24-13(3)17-10-18(32-16(6)27)20(14(4)31-15(5)26)21(17)22(23(24)29)25(7)11-30-25/h9,14,17-18,20-24,29H,3,8,10-11H2,1-2,4-7H3/b12-9+/t14-,17-,18-,20-,21-,22-,23+,24-,25+/m0/s1
SMILES:	CCC(=CC(=O)OC1C(C(C2C(C1=C)CC(C2C(C)OC(=O)C)OC(=O)C)C3(CO3)C)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2334362
PubChem CID:	71719446
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[455253]
NPT83	Cell Line	MCF7	Homo sapiens	EC50	>	20.0	ug.mL-1	PMID[455253]
NPT91	Cell Line	KB	Homo sapiens	EC50	>	20.0	ug.mL-1	PMID[455253]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	EC50	>	20.0	ug.mL-1	PMID[455253]

☑ 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 NPC470972 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	1380
0.2-0.3	4595
0.3-0.4	9308
0.4-0.5	12720
0.5-0.6	7165
0.6-0.7	5716
0.7-0.8	1506
0.8-0.85	102
0.85-0.9	2
0.9-0.95	2
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9691	High Similarity	NPC470980
0.8627	High Similarity	NPC474550
0.8627	High Similarity	NPC473577
0.8627	High Similarity	NPC475585
0.8598	High Similarity	NPC216665
0.8544	High Similarity	NPC475290
0.8529	High Similarity	NPC474124
0.8515	High Similarity	NPC472554
0.8515	High Similarity	NPC475617
0.8447	Intermediate Similarity	NPC473543
0.8431	Intermediate Similarity	NPC476471
0.8431	Intermediate Similarity	NPC475344
0.8431	Intermediate Similarity	NPC472552
0.8426	Intermediate Similarity	NPC43213
0.84	Intermediate Similarity	NPC472998
0.8384	Intermediate Similarity	NPC469583
0.8365	Intermediate Similarity	NPC186668
0.8365	Intermediate Similarity	NPC470979
0.8365	Intermediate Similarity	NPC103088
0.8365	Intermediate Similarity	NPC119855
0.8365	Intermediate Similarity	NPC220217
0.8365	Intermediate Similarity	NPC470975
0.835	Intermediate Similarity	NPC475623
0.835	Intermediate Similarity	NPC475334
0.835	Intermediate Similarity	NPC472821
0.835	Intermediate Similarity	NPC473523
0.835	Intermediate Similarity	NPC473694
0.8318	Intermediate Similarity	NPC470076
0.8302	Intermediate Similarity	NPC471934
0.83	Intermediate Similarity	NPC472996
0.83	Intermediate Similarity	NPC472997
0.83	Intermediate Similarity	NPC472995
0.8288	Intermediate Similarity	NPC278681
0.8288	Intermediate Similarity	NPC472667
0.8273	Intermediate Similarity	NPC290693
0.8273	Intermediate Similarity	NPC203862
0.8273	Intermediate Similarity	NPC152615
0.8269	Intermediate Similarity	NPC181104
0.8269	Intermediate Similarity	NPC121518
0.8269	Intermediate Similarity	NPC201144
0.8269	Intermediate Similarity	NPC103298
0.8269	Intermediate Similarity	NPC80809
0.8269	Intermediate Similarity	NPC475331
0.8269	Intermediate Similarity	NPC475335
0.8269	Intermediate Similarity	NPC288502
0.8241	Intermediate Similarity	NPC471933
0.8235	Intermediate Similarity	NPC230546
0.8235	Intermediate Similarity	NPC272223
0.8235	Intermediate Similarity	NPC473510
0.8235	Intermediate Similarity	NPC38855
0.823	Intermediate Similarity	NPC115349
0.8218	Intermediate Similarity	NPC475033
0.8218	Intermediate Similarity	NPC254121
0.8218	Intermediate Similarity	NPC210337
0.8218	Intermediate Similarity	NPC475032
0.8214	Intermediate Similarity	NPC112936
0.8208	Intermediate Similarity	NPC88701
0.8208	Intermediate Similarity	NPC181994
0.82	Intermediate Similarity	NPC329435
0.8198	Intermediate Similarity	NPC16701
0.819	Intermediate Similarity	NPC60315
0.8182	Intermediate Similarity	NPC199428
0.8182	Intermediate Similarity	NPC5311
0.8182	Intermediate Similarity	NPC310341
0.8182	Intermediate Similarity	NPC193382
0.8182	Intermediate Similarity	NPC470075
0.8182	Intermediate Similarity	NPC99620
0.8173	Intermediate Similarity	NPC187302
0.8173	Intermediate Similarity	NPC196471
0.8173	Intermediate Similarity	NPC189588
0.8173	Intermediate Similarity	NPC97487
0.8173	Intermediate Similarity	NPC10232
0.8173	Intermediate Similarity	NPC160583
0.8155	Intermediate Similarity	NPC268829
0.8155	Intermediate Similarity	NPC222875
0.8155	Intermediate Similarity	NPC247701
0.8155	Intermediate Similarity	NPC25177
0.8155	Intermediate Similarity	NPC295110
0.8155	Intermediate Similarity	NPC11974
0.8142	Intermediate Similarity	NPC233500
0.8131	Intermediate Similarity	NPC257853
0.8125	Intermediate Similarity	NPC304260
0.8125	Intermediate Similarity	NPC44899
0.8125	Intermediate Similarity	NPC5883
0.8125	Intermediate Similarity	NPC29639
0.8125	Intermediate Similarity	NPC219656
0.8125	Intermediate Similarity	NPC213761
0.8125	Intermediate Similarity	NPC329905
0.8125	Intermediate Similarity	NPC35171
0.8119	Intermediate Similarity	NPC475304
0.8119	Intermediate Similarity	NPC88009
0.8108	Intermediate Similarity	NPC93883
0.8108	Intermediate Similarity	NPC471354
0.8108	Intermediate Similarity	NPC471353
0.8108	Intermediate Similarity	NPC474418
0.8108	Intermediate Similarity	NPC142066
0.8108	Intermediate Similarity	NPC309034
0.8108	Intermediate Similarity	NPC157380
0.8108	Intermediate Similarity	NPC157376
0.8108	Intermediate Similarity	NPC158344
0.8108	Intermediate Similarity	NPC185287
0.8108	Intermediate Similarity	NPC471355
0.8108	Intermediate Similarity	NPC473852
0.8108	Intermediate Similarity	NPC471351
0.8108	Intermediate Similarity	NPC243196
0.8108	Intermediate Similarity	NPC196429
0.8108	Intermediate Similarity	NPC77319
0.8108	Intermediate Similarity	NPC84987
0.8108	Intermediate Similarity	NPC27507
0.8108	Intermediate Similarity	NPC244402
0.8108	Intermediate Similarity	NPC99728
0.8108	Intermediate Similarity	NPC50305
0.8108	Intermediate Similarity	NPC34390
0.8108	Intermediate Similarity	NPC87250
0.8091	Intermediate Similarity	NPC84949
0.8091	Intermediate Similarity	NPC69576
0.8091	Intermediate Similarity	NPC178289
0.8091	Intermediate Similarity	NPC31354
0.8091	Intermediate Similarity	NPC471633
0.8081	Intermediate Similarity	NPC122057
0.8077	Intermediate Similarity	NPC214714
0.8077	Intermediate Similarity	NPC475038
0.8077	Intermediate Similarity	NPC11956
0.8077	Intermediate Similarity	NPC109195
0.8077	Intermediate Similarity	NPC200672
0.8077	Intermediate Similarity	NPC165578
0.807	Intermediate Similarity	NPC196130
0.8058	Intermediate Similarity	NPC79303
0.8056	Intermediate Similarity	NPC177047
0.8056	Intermediate Similarity	NPC472215
0.8056	Intermediate Similarity	NPC472214
0.8053	Intermediate Similarity	NPC475136
0.8053	Intermediate Similarity	NPC143755
0.8053	Intermediate Similarity	NPC474466
0.8039	Intermediate Similarity	NPC205143
0.8039	Intermediate Similarity	NPC347923
0.8039	Intermediate Similarity	NPC274793
0.8039	Intermediate Similarity	NPC476057
0.8036	Intermediate Similarity	NPC218093
0.8036	Intermediate Similarity	NPC83287
0.802	Intermediate Similarity	NPC276110
0.802	Intermediate Similarity	NPC220221
0.802	Intermediate Similarity	NPC476720
0.802	Intermediate Similarity	NPC86893
0.802	Intermediate Similarity	NPC292178
0.8019	Intermediate Similarity	NPC93026
0.8019	Intermediate Similarity	NPC265502
0.8019	Intermediate Similarity	NPC469960
0.8019	Intermediate Similarity	NPC29389
0.8018	Intermediate Similarity	NPC470793
0.8	Intermediate Similarity	NPC53555
0.8	Intermediate Similarity	NPC23584
0.8	Intermediate Similarity	NPC281378
0.8	Intermediate Similarity	NPC171126
0.7982	Intermediate Similarity	NPC310511
0.7982	Intermediate Similarity	NPC475219
0.7982	Intermediate Similarity	NPC71680
0.7982	Intermediate Similarity	NPC231518
0.7981	Intermediate Similarity	NPC49532
0.7981	Intermediate Similarity	NPC26557
0.7981	Intermediate Similarity	NPC155974
0.7966	Intermediate Similarity	NPC475371
0.7965	Intermediate Similarity	NPC30483
0.7965	Intermediate Similarity	NPC475041
0.7965	Intermediate Similarity	NPC470897
0.7965	Intermediate Similarity	NPC291820
0.7965	Intermediate Similarity	NPC55532
0.7965	Intermediate Similarity	NPC469756
0.7965	Intermediate Similarity	NPC268326
0.7965	Intermediate Similarity	NPC32177
0.7965	Intermediate Similarity	NPC236973
0.7965	Intermediate Similarity	NPC153085
0.7965	Intermediate Similarity	NPC292467
0.7965	Intermediate Similarity	NPC81222
0.7961	Intermediate Similarity	NPC474957
0.7961	Intermediate Similarity	NPC79449
0.7961	Intermediate Similarity	NPC274458
0.7944	Intermediate Similarity	NPC469959
0.7944	Intermediate Similarity	NPC475781
0.7944	Intermediate Similarity	NPC472820
0.7944	Intermediate Similarity	NPC471205
0.7944	Intermediate Similarity	NPC473586
0.7944	Intermediate Similarity	NPC469957
0.7944	Intermediate Similarity	NPC108682
0.7944	Intermediate Similarity	NPC472263
0.7941	Intermediate Similarity	NPC72204
0.7925	Intermediate Similarity	NPC161775
0.7925	Intermediate Similarity	NPC152966
0.7921	Intermediate Similarity	NPC140277
0.7921	Intermediate Similarity	NPC105490
0.7913	Intermediate Similarity	NPC23786
0.7913	Intermediate Similarity	NPC470265
0.7913	Intermediate Similarity	NPC269642
0.7913	Intermediate Similarity	NPC193893
0.7909	Intermediate Similarity	NPC241477
0.7905	Intermediate Similarity	NPC252242
0.7905	Intermediate Similarity	NPC475956
0.79	Intermediate Similarity	NPC91251
0.7895	Intermediate Similarity	NPC475629
0.7895	Intermediate Similarity	NPC107607

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 NPC470972 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	164
0.1-0.2	1704
0.2-0.3	3878
0.3-0.4	2303
0.4-0.5	675
0.5-0.6	248
0.6-0.7	155
0.7-0.8	22
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8515	High Similarity	NPD5344	Discontinued
0.8125	Intermediate Similarity	NPD7516	Approved
0.8058	Intermediate Similarity	NPD6648	Approved
0.8036	Intermediate Similarity	NPD7327	Approved
0.8036	Intermediate Similarity	NPD7328	Approved
0.7982	Intermediate Similarity	NPD8033	Approved
0.7895	Intermediate Similarity	NPD8377	Approved
0.7895	Intermediate Similarity	NPD8294	Approved
0.7826	Intermediate Similarity	NPD8378	Approved
0.7826	Intermediate Similarity	NPD8335	Approved
0.7826	Intermediate Similarity	NPD8296	Approved
0.7826	Intermediate Similarity	NPD8380	Approved
0.7826	Intermediate Similarity	NPD8379	Approved
0.78	Intermediate Similarity	NPD7838	Discovery
0.78	Intermediate Similarity	NPD46	Approved
0.78	Intermediate Similarity	NPD6698	Approved
0.7788	Intermediate Similarity	NPD7638	Approved
0.7714	Intermediate Similarity	NPD7639	Approved
0.7714	Intermediate Similarity	NPD7640	Approved
0.7672	Intermediate Similarity	NPD7503	Approved
0.7563	Intermediate Similarity	NPD7507	Approved
0.7478	Intermediate Similarity	NPD7115	Discovery
0.7477	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7453	Intermediate Similarity	NPD4225	Approved
0.7377	Intermediate Similarity	NPD7319	Approved
0.7297	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7281	Intermediate Similarity	NPD6053	Discontinued
0.7257	Intermediate Similarity	NPD6371	Approved
0.7257	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7232	Intermediate Similarity	NPD6686	Approved
0.7157	Intermediate Similarity	NPD7524	Approved
0.7143	Intermediate Similarity	NPD6319	Approved
0.713	Intermediate Similarity	NPD8297	Approved
0.7091	Intermediate Similarity	NPD7632	Discontinued
0.7069	Intermediate Similarity	NPD4632	Approved
0.7054	Intermediate Similarity	NPD6675	Approved
0.7054	Intermediate Similarity	NPD6008	Approved
0.7054	Intermediate Similarity	NPD7128	Approved
0.7054	Intermediate Similarity	NPD6402	Approved
0.7054	Intermediate Similarity	NPD5739	Approved
0.7018	Intermediate Similarity	NPD6373	Approved
0.7018	Intermediate Similarity	NPD6372	Approved
0.6991	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6961	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.693	Remote Similarity	NPD6881	Approved
0.693	Remote Similarity	NPD7320	Approved
0.693	Remote Similarity	NPD6899	Approved
0.6897	Remote Similarity	NPD6649	Approved
0.6897	Remote Similarity	NPD6650	Approved
0.6863	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD6051	Approved
0.6847	Remote Similarity	NPD4159	Approved
0.6842	Remote Similarity	NPD5701	Approved
0.6842	Remote Similarity	NPD5697	Approved
0.6842	Remote Similarity	NPD6412	Phase 2
0.6838	Remote Similarity	NPD6882	Approved
0.6829	Remote Similarity	NPD7604	Phase 2
0.6827	Remote Similarity	NPD4251	Approved
0.6827	Remote Similarity	NPD4250	Approved
0.6818	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.681	Remote Similarity	NPD6883	Approved
0.681	Remote Similarity	NPD7290	Approved
0.681	Remote Similarity	NPD7102	Approved
0.68	Remote Similarity	NPD4819	Approved
0.68	Remote Similarity	NPD4822	Approved
0.68	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.68	Remote Similarity	NPD4820	Approved
0.68	Remote Similarity	NPD4821	Approved
0.6792	Remote Similarity	NPD3168	Discontinued
0.6789	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.678	Remote Similarity	NPD8133	Approved
0.6774	Remote Similarity	NPD7492	Approved
0.6765	Remote Similarity	NPD6695	Phase 3
0.6752	Remote Similarity	NPD6617	Approved
0.6752	Remote Similarity	NPD6847	Approved
0.6752	Remote Similarity	NPD8130	Phase 1
0.6752	Remote Similarity	NPD6869	Approved
0.675	Remote Similarity	NPD6009	Approved
0.6731	Remote Similarity	NPD4249	Approved
0.6729	Remote Similarity	NPD7637	Suspended
0.6727	Remote Similarity	NPD6084	Phase 2
0.6727	Remote Similarity	NPD6083	Phase 2
0.6724	Remote Similarity	NPD6014	Approved
0.6724	Remote Similarity	NPD6012	Approved
0.6724	Remote Similarity	NPD6013	Approved
0.6721	Remote Similarity	NPD6054	Approved
0.6721	Remote Similarity	NPD6059	Approved
0.672	Remote Similarity	NPD6616	Approved
0.6698	Remote Similarity	NPD1695	Approved
0.6667	Remote Similarity	NPD7078	Approved
0.6667	Remote Similarity	NPD8293	Discontinued
0.6667	Remote Similarity	NPD5983	Phase 2
0.6638	Remote Similarity	NPD6011	Approved
0.6634	Remote Similarity	NPD7525	Registered
0.6614	Remote Similarity	NPD7736	Approved
0.6613	Remote Similarity	NPD6370	Approved
0.661	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6602	Remote Similarity	NPD5362	Discontinued
0.66	Remote Similarity	NPD4271	Approved
0.66	Remote Similarity	NPD4268	Approved
0.6587	Remote Similarity	NPD6336	Discontinued
0.6577	Remote Similarity	NPD4755	Approved
0.6574	Remote Similarity	NPD7983	Approved
0.6545	Remote Similarity	NPD5695	Phase 3
0.6532	Remote Similarity	NPD6015	Approved
0.6532	Remote Similarity	NPD6016	Approved
0.6525	Remote Similarity	NPD4634	Approved
0.6522	Remote Similarity	NPD7625	Phase 1
0.6514	Remote Similarity	NPD4202	Approved
0.6514	Remote Similarity	NPD6399	Phase 3
0.6509	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6509	Remote Similarity	NPD7750	Discontinued
0.6496	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6491	Remote Similarity	NPD3653	Clinical (unspecified phase)
0.6491	Remote Similarity	NPD5211	Phase 2
0.6481	Remote Similarity	NPD5785	Approved
0.648	Remote Similarity	NPD5988	Approved
0.6471	Remote Similarity	NPD6930	Phase 2
0.6471	Remote Similarity	NPD6931	Approved
0.6471	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.646	Remote Similarity	NPD4696	Approved
0.646	Remote Similarity	NPD5285	Approved
0.646	Remote Similarity	NPD5286	Approved
0.646	Remote Similarity	NPD4700	Approved
0.6442	Remote Similarity	NPD5332	Approved
0.6442	Remote Similarity	NPD5331	Approved
0.6408	Remote Similarity	NPD4790	Discontinued
0.64	Remote Similarity	NPD8515	Approved
0.64	Remote Similarity	NPD6933	Approved
0.64	Remote Similarity	NPD8513	Phase 3
0.64	Remote Similarity	NPD8516	Approved
0.64	Remote Similarity	NPD8517	Approved
0.6396	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6393	Remote Similarity	NPD6274	Approved
0.6383	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6381	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6379	Remote Similarity	NPD5141	Approved
0.6373	Remote Similarity	NPD6929	Approved
0.6372	Remote Similarity	NPD5696	Approved
0.6371	Remote Similarity	NPD7100	Approved
0.6371	Remote Similarity	NPD7101	Approved
0.6364	Remote Similarity	NPD5778	Approved
0.6364	Remote Similarity	NPD5779	Approved
0.6348	Remote Similarity	NPD5224	Approved
0.6348	Remote Similarity	NPD5225	Approved
0.6348	Remote Similarity	NPD5226	Approved
0.6348	Remote Similarity	NPD4633	Approved
0.6346	Remote Similarity	NPD6435	Approved
0.6325	Remote Similarity	NPD4767	Approved
0.6325	Remote Similarity	NPD5357	Phase 1
0.6325	Remote Similarity	NPD4768	Approved
0.6321	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6321	Remote Similarity	NPD5363	Approved
0.6311	Remote Similarity	NPD7514	Phase 3
0.6303	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6293	Remote Similarity	NPD5175	Approved
0.6293	Remote Similarity	NPD5174	Approved
0.629	Remote Similarity	NPD6335	Approved
0.6286	Remote Similarity	NPD7154	Phase 3
0.6273	Remote Similarity	NPD7087	Discontinued
0.6273	Remote Similarity	NPD5693	Phase 1
0.627	Remote Similarity	NPD6908	Approved
0.627	Remote Similarity	NPD6909	Approved
0.6262	Remote Similarity	NPD7146	Approved
0.6262	Remote Similarity	NPD5330	Approved
0.6262	Remote Similarity	NPD7521	Approved
0.6262	Remote Similarity	NPD7334	Approved
0.6262	Remote Similarity	NPD6684	Approved
0.6262	Remote Similarity	NPD6409	Approved
0.6261	Remote Similarity	NPD5223	Approved
0.625	Remote Similarity	NPD6902	Approved
0.625	Remote Similarity	NPD5369	Approved
0.6239	Remote Similarity	NPD4753	Phase 2
0.6239	Remote Similarity	NPD5328	Approved
0.6238	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6231	Remote Similarity	NPD6033	Approved
0.6218	Remote Similarity	NPD4730	Approved
0.6218	Remote Similarity	NPD4729	Approved
0.621	Remote Similarity	NPD6317	Approved
0.62	Remote Similarity	NPD6926	Approved
0.62	Remote Similarity	NPD6924	Approved
0.619	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.619	Remote Similarity	NPD4270	Approved
0.619	Remote Similarity	NPD4269	Approved
0.6176	Remote Similarity	NPD5776	Phase 2
0.6176	Remote Similarity	NPD6932	Approved
0.6176	Remote Similarity	NPD6925	Approved
0.6172	Remote Similarity	NPD6067	Discontinued
0.6172	Remote Similarity	NPD8328	Phase 3
0.6168	Remote Similarity	NPD6893	Approved
0.6161	Remote Similarity	NPD7748	Approved
0.616	Remote Similarity	NPD6313	Approved
0.616	Remote Similarity	NPD6314	Approved
0.6154	Remote Similarity	NPD7332	Phase 2
0.6154	Remote Similarity	NPD5368	Approved
0.6154	Remote Similarity	NPD8074	Phase 3
0.6154	Remote Similarity	NPD4754	Approved
0.6147	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6147	Remote Similarity	NPD6903	Approved
0.614	Remote Similarity	NPD7902	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