NPASS Compound

Structure

NPC473920 OpenBabel07101718242D 39 44 0 0 1 0 0 0 0 0999 V2000 3.1055 4.7930 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8376 -1.2070 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1055 0.7930 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7036 2.2930 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.4357 4.2930 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8376 4.7930 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1055 2.7930 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2350 0.0658 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 7.2425 0.7930 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9716 4.2930 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.8376 -0.2070 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.9716 3.2930 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 3.9716 0.2930 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.7036 4.2930 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.1055 1.7930 0.0000 C 0 0 2 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 -0.8660 1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 2.0000 0.0000 C 0 0 1 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 5.7036 0.2930 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.7036 1.2930 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.8376 1.7930 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.7036 3.2930 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 3.9716 1.2930 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.8376 2.7930 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5981 0.5000 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 -0.0000 3.0000 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 6.5696 2.7930 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.5696 4.7930 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.6547 -0.0160 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.6547 1.6020 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 2.5405 1.2687 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5 34 1 0 0 0 0 6 11 1 0 0 0 0 6 15 2 0 0 0 0 7 13 1 0 0 0 0 7 17 1 0 0 0 0 8 14 1 0 0 0 0 8 18 1 0 0 0 0 9 29 1 0 0 0 0 10 35 1 0 0 0 0 10 36 1 0 0 0 0 11 1 1 6 0 0 0 11 13 1 0 0 0 0 12 2 1 6 0 0 0 12 14 1 0 0 0 0 12 22 1 0 0 0 0 13 28 1 0 0 0 0 14 27 1 6 0 0 0 15 25 1 0 0 0 0 15 34 1 0 0 0 0 16 9 1 6 0 0 0 16 19 1 0 0 0 0 16 37 1 0 0 0 0 17 27 1 6 0 0 0 17 38 1 0 0 0 0 18 38 1 0 0 0 0 18 39 1 6 0 0 0 19 20 1 0 0 0 0 19 30 1 1 0 0 0 20 21 1 0 0 0 0 20 31 1 6 0 0 0 21 26 1 0 0 0 0 21 32 1 1 0 0 0 22 23 1 0 0 0 0 22 35 1 1 0 0 0 23 24 1 0 0 0 0 23 36 1 6 0 0 0 24 27 1 1 0 0 0 24 28 1 0 0 0 0 25 28 1 0 0 0 0 25 33 2 0 0 0 0 26 37 1 0 0 0 0 26 39 1 6 0 0 0 27 3 1 1 0 0 0 28 4 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	554.27
Volume:	532.925
LogP:	1.626
LogD:	2.225
LogS:	-3.994
# Rotatable Bonds:	4
TPSA:	153.37
# H-Bond Aceptor:	11
# H-Bond Donor:	4
# Rings:	6
# Heavy Atoms:	11

MedChem Properties

QED Drug-Likeness Score:	0.38
Synthetic Accessibility Score:	5.81
Fsp3:	0.893
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.188
MDCK Permeability:	9.997211600420997e-05
Pgp-inhibitor:	0.989
Pgp-substrate:	0.975
Human Intestinal Absorption (HIA):	0.394
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.944

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.122
Plasma Protein Binding (PPB):	41.9210319519043%
Volume Distribution (VD):	0.82
Pgp-substrate:	29.37997817993164%

ADMET: Metabolism

CYP1A2-inhibitor:	0.007
CYP1A2-substrate:	0.982
CYP2C19-inhibitor:	0.011
CYP2C19-substrate:	0.832
CYP2C9-inhibitor:	0.002
CYP2C9-substrate:	0.015
CYP2D6-inhibitor:	0.004
CYP2D6-substrate:	0.115
CYP3A4-inhibitor:	0.11
CYP3A4-substrate:	0.383

ADMET: Excretion

Clearance (CL):	1.169
Half-life (T1/2):	0.669

ADMET: Toxicity

hERG Blockers:	0.07
Human Hepatotoxicity (H-HT):	0.439
Drug-inuced Liver Injury (DILI):	0.05
AMES Toxicity:	0.127
Rat Oral Acute Toxicity:	0.121
Maximum Recommended Daily Dose:	0.167
Skin Sensitization:	0.242
Carcinogencity:	0.092
Eye Corrosion:	0.003
Eye Irritation:	0.015
Respiratory Toxicity:	0.975

Download Data

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

Natural Product: NPC473920

Natural Product ID:	NPC473920
*Common Name:**	Picrasinoside C
IUPAC Name:	n.a.
Synonyms:	Picrasinoside C
Standard InCHIKey:	OXASTUFERDOEDO-BLLJQZPCSA-N
Standard InCHI:	InChI=1S/C28H42O11/c1-11-6-15(34-5)25(33)28(4)13(11)7-17-27(3)14(12(2)22-23(24(27)28)36-10-35-22)8-18(38-17)39-26-21(32)20(31)19(30)16(9-29)37-26/h6,11-14,16-24,26,29-32H,7-10H2,1-5H3/t11-,12-,13?,14+,16-,17-,18+,19-,20+,21-,22+,23-,24+,26+,27-,28+/m1/s1
SMILES:	CC1C=C(C(=O)C2(C1CC3C4(C2C5C(C(C4CC(O3)OC6C(C(C(C(O6)CO)O)O)O)C)OCO5)C)C)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL455293
PubChem CID:	44576017
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones [CHEMONTID:0002119] Quassinoids

*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
NPO1268	Picrasma ailanthoides	Species	Simaroubaceae	Eukaryota	stem wood	n.a.	n.a.	PMID[1955884]
NPO1268	Picrasma ailanthoides	Species	Simaroubaceae	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
ED50	6

Activity Type	# Activity
Cell Line	5
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	ED50	<=	4.0	ug ml-1	PMID[465059]
NPT672	Cell Line	TE-671	Homo sapiens	ED50	<=	4.0	ug ml-1	PMID[465059]
NPT81	Cell Line	A549	Homo sapiens	ED50	<=	4.0	ug ml-1	PMID[465059]
NPT180	Cell Line	HCT-8	Homo sapiens	ED50	<=	4.0	ug ml-1	PMID[465059]
NPT168	Cell Line	P388	Mus musculus	ED50	<=	4.0	ug ml-1	PMID[465059]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	ED50	<=	4.0	ug ml-1	PMID[465059]

☑ 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 NPC473920 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	275
0.1-0.2	1808
0.2-0.3	5409
0.3-0.4	9122
0.4-0.5	11251
0.5-0.6	7603
0.6-0.7	4466
0.7-0.8	2184
0.8-0.85	507
0.85-0.9	60
0.9-0.95	10
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9646	High Similarity	NPC227397
0.964	High Similarity	NPC279143
0.964	High Similarity	NPC127530
0.9469	High Similarity	NPC275675
0.9375	High Similarity	NPC176005
0.9316	High Similarity	NPC295220
0.9316	High Similarity	NPC475636
0.9237	High Similarity	NPC309096
0.9237	High Similarity	NPC54614
0.8983	High Similarity	NPC87662
0.8947	High Similarity	NPC309433
0.8829	High Similarity	NPC27814
0.8824	High Similarity	NPC285091
0.879	High Similarity	NPC190065
0.879	High Similarity	NPC141215
0.879	High Similarity	NPC471089
0.8772	High Similarity	NPC474906
0.8772	High Similarity	NPC18547
0.8739	High Similarity	NPC177820
0.8739	High Similarity	NPC30188
0.8729	High Similarity	NPC471965
0.872	High Similarity	NPC295885
0.872	High Similarity	NPC596
0.872	High Similarity	NPC140045
0.871	High Similarity	NPC262813
0.8696	High Similarity	NPC152199
0.8696	High Similarity	NPC235539
0.8696	High Similarity	NPC134869
0.8678	High Similarity	NPC293623
0.8678	High Similarity	NPC69273
0.8678	High Similarity	NPC168899
0.8655	High Similarity	NPC471961
0.8655	High Similarity	NPC14617
0.8655	High Similarity	NPC471964
0.8655	High Similarity	NPC262199
0.8655	High Similarity	NPC202666
0.864	High Similarity	NPC251998
0.8609	High Similarity	NPC102088
0.8596	High Similarity	NPC289312
0.8596	High Similarity	NPC11252
0.8583	High Similarity	NPC471962
0.8583	High Similarity	NPC469841
0.8583	High Similarity	NPC7850
0.8583	High Similarity	NPC471963
0.8583	High Similarity	NPC277191
0.8583	High Similarity	NPC190846
0.8583	High Similarity	NPC6615
0.8583	High Similarity	NPC469842
0.8583	High Similarity	NPC247315
0.8571	High Similarity	NPC107966
0.8571	High Similarity	NPC272576
0.8571	High Similarity	NPC249848
0.8571	High Similarity	NPC40775
0.8571	High Similarity	NPC235438
0.8559	High Similarity	NPC109607
0.8559	High Similarity	NPC107338
0.8547	High Similarity	NPC297179
0.8537	High Similarity	NPC478155
0.8537	High Similarity	NPC25998
0.8537	High Similarity	NPC241008
0.8534	High Similarity	NPC96312
0.8534	High Similarity	NPC40632
0.8534	High Similarity	NPC251236
0.8534	High Similarity	NPC328374
0.8522	High Similarity	NPC293038
0.8522	High Similarity	NPC62696
0.8509	High Similarity	NPC201992
0.85	High Similarity	NPC478066
0.85	High Similarity	NPC30735
0.85	High Similarity	NPC235405
0.85	High Similarity	NPC281148
0.8487	Intermediate Similarity	NPC241310
0.8487	Intermediate Similarity	NPC412
0.8487	Intermediate Similarity	NPC131841
0.8487	Intermediate Similarity	NPC258789
0.8487	Intermediate Similarity	NPC258815
0.8487	Intermediate Similarity	NPC47567
0.8487	Intermediate Similarity	NPC169727
0.8487	Intermediate Similarity	NPC278163
0.8487	Intermediate Similarity	NPC187950
0.8487	Intermediate Similarity	NPC42675
0.8487	Intermediate Similarity	NPC194310
0.8475	Intermediate Similarity	NPC214484
0.8475	Intermediate Similarity	NPC192791
0.8475	Intermediate Similarity	NPC469945
0.8475	Intermediate Similarity	NPC475775
0.8475	Intermediate Similarity	NPC473401
0.8475	Intermediate Similarity	NPC6377
0.8475	Intermediate Similarity	NPC35405
0.8475	Intermediate Similarity	NPC309780
0.8475	Intermediate Similarity	NPC208381
0.8475	Intermediate Similarity	NPC39211
0.8475	Intermediate Similarity	NPC180550
0.8475	Intermediate Similarity	NPC11551
0.8475	Intermediate Similarity	NPC476529
0.8475	Intermediate Similarity	NPC114441
0.8475	Intermediate Similarity	NPC157868
0.8475	Intermediate Similarity	NPC472949
0.8475	Intermediate Similarity	NPC473884
0.8475	Intermediate Similarity	NPC470777
0.8475	Intermediate Similarity	NPC475171
0.8468	Intermediate Similarity	NPC478154
0.8468	Intermediate Similarity	NPC478153
0.8468	Intermediate Similarity	NPC478152
0.8468	Intermediate Similarity	NPC478150
0.8462	Intermediate Similarity	NPC477252
0.8455	Intermediate Similarity	NPC477196
0.8448	Intermediate Similarity	NPC473798
0.843	Intermediate Similarity	NPC475194
0.843	Intermediate Similarity	NPC470477
0.8417	Intermediate Similarity	NPC162574
0.8417	Intermediate Similarity	NPC213952
0.84	Intermediate Similarity	NPC478151
0.839	Intermediate Similarity	NPC286347
0.839	Intermediate Similarity	NPC109588
0.8387	Intermediate Similarity	NPC475377
0.8387	Intermediate Similarity	NPC173435
0.8387	Intermediate Similarity	NPC475167
0.8387	Intermediate Similarity	NPC478065
0.8387	Intermediate Similarity	NPC262796
0.8387	Intermediate Similarity	NPC264566
0.8387	Intermediate Similarity	NPC172374
0.8387	Intermediate Similarity	NPC329993
0.8387	Intermediate Similarity	NPC476074
0.8387	Intermediate Similarity	NPC477197
0.8387	Intermediate Similarity	NPC478064
0.8387	Intermediate Similarity	NPC45346
0.8387	Intermediate Similarity	NPC134914
0.8387	Intermediate Similarity	NPC301639
0.8376	Intermediate Similarity	NPC173686
0.8376	Intermediate Similarity	NPC16081
0.8376	Intermediate Similarity	NPC31797
0.8374	Intermediate Similarity	NPC477191
0.8374	Intermediate Similarity	NPC477194
0.8374	Intermediate Similarity	NPC477192
0.8374	Intermediate Similarity	NPC477193
0.8362	Intermediate Similarity	NPC49451
0.8362	Intermediate Similarity	NPC198539
0.8362	Intermediate Similarity	NPC51978
0.8361	Intermediate Similarity	NPC470218
0.8347	Intermediate Similarity	NPC238005
0.8347	Intermediate Similarity	NPC1980
0.8347	Intermediate Similarity	NPC257211
0.8347	Intermediate Similarity	NPC141196
0.8333	Intermediate Similarity	NPC64715
0.8333	Intermediate Similarity	NPC104372
0.8333	Intermediate Similarity	NPC171544
0.8333	Intermediate Similarity	NPC301449
0.8333	Intermediate Similarity	NPC297263
0.8333	Intermediate Similarity	NPC62725
0.8333	Intermediate Similarity	NPC114484
0.8333	Intermediate Similarity	NPC31838
0.8333	Intermediate Similarity	NPC242840
0.8333	Intermediate Similarity	NPC75417
0.8333	Intermediate Similarity	NPC223301
0.8333	Intermediate Similarity	NPC222580
0.8333	Intermediate Similarity	NPC22956
0.8333	Intermediate Similarity	NPC86222
0.8333	Intermediate Similarity	NPC31193
0.8333	Intermediate Similarity	NPC11242
0.8333	Intermediate Similarity	NPC159309
0.832	Intermediate Similarity	NPC476776
0.832	Intermediate Similarity	NPC477195
0.8319	Intermediate Similarity	NPC319570
0.8319	Intermediate Similarity	NPC258592
0.8319	Intermediate Similarity	NPC197003
0.8319	Intermediate Similarity	NPC178548
0.8319	Intermediate Similarity	NPC122971
0.8319	Intermediate Similarity	NPC190939
0.8319	Intermediate Similarity	NPC469488
0.8306	Intermediate Similarity	NPC305793
0.8306	Intermediate Similarity	NPC1314
0.8306	Intermediate Similarity	NPC252657
0.8306	Intermediate Similarity	NPC11577
0.8306	Intermediate Similarity	NPC244296
0.8306	Intermediate Similarity	NPC107536
0.8306	Intermediate Similarity	NPC9470
0.8306	Intermediate Similarity	NPC477076
0.8306	Intermediate Similarity	NPC280029
0.8306	Intermediate Similarity	NPC252289
0.8306	Intermediate Similarity	NPC115656
0.8306	Intermediate Similarity	NPC470518
0.8306	Intermediate Similarity	NPC472267
0.8306	Intermediate Similarity	NPC269484
0.8306	Intermediate Similarity	NPC141600
0.8306	Intermediate Similarity	NPC88311
0.8306	Intermediate Similarity	NPC470913
0.8306	Intermediate Similarity	NPC82380
0.8306	Intermediate Similarity	NPC477079
0.8306	Intermediate Similarity	NPC97918
0.8306	Intermediate Similarity	NPC273878
0.8306	Intermediate Similarity	NPC477077
0.8305	Intermediate Similarity	NPC224121
0.8293	Intermediate Similarity	NPC470780
0.8291	Intermediate Similarity	NPC475633
0.8291	Intermediate Similarity	NPC268238
0.8291	Intermediate Similarity	NPC470919
0.8291	Intermediate Similarity	NPC469877
0.8291	Intermediate Similarity	NPC323821
0.8291	Intermediate Similarity	NPC143268

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 NPC473920 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	242
0.1-0.2	2104
0.2-0.3	4058
0.3-0.4	1744
0.4-0.5	526
0.5-0.6	269
0.6-0.7	134
0.7-0.8	70
0.8-0.85	3
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8655	High Similarity	NPD8328	Phase 3
0.8305	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.8174	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.8115	Intermediate Similarity	NPD6370	Approved
0.8	Intermediate Similarity	NPD6412	Phase 2
0.7951	Intermediate Similarity	NPD6054	Approved
0.7937	Intermediate Similarity	NPD7736	Approved
0.7805	Intermediate Similarity	NPD6059	Approved
0.7742	Intermediate Similarity	NPD6016	Approved
0.7742	Intermediate Similarity	NPD6015	Approved
0.7717	Intermediate Similarity	NPD8293	Discontinued
0.7698	Intermediate Similarity	NPD7492	Approved
0.768	Intermediate Similarity	NPD5988	Approved
0.7667	Intermediate Similarity	NPD6882	Approved
0.7638	Intermediate Similarity	NPD6616	Approved
0.7627	Intermediate Similarity	NPD6686	Approved
0.7578	Intermediate Similarity	NPD7078	Approved
0.7561	Intermediate Similarity	NPD6009	Approved
0.7521	Intermediate Similarity	NPD8297	Approved
0.752	Intermediate Similarity	NPD6319	Approved
0.75	Intermediate Similarity	NPD7507	Approved
0.7438	Intermediate Similarity	NPD6650	Approved
0.7438	Intermediate Similarity	NPD6649	Approved
0.7417	Intermediate Similarity	NPD6372	Approved
0.7417	Intermediate Similarity	NPD6373	Approved
0.7373	Intermediate Similarity	NPD8170	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD6881	Approved
0.7333	Intermediate Similarity	NPD6899	Approved
0.7328	Intermediate Similarity	NPD7319	Approved
0.7323	Intermediate Similarity	NPD7503	Approved
0.7317	Intermediate Similarity	NPD4632	Approved
0.7311	Intermediate Similarity	NPD7128	Approved
0.7311	Intermediate Similarity	NPD5739	Approved
0.7311	Intermediate Similarity	NPD6675	Approved
0.7311	Intermediate Similarity	NPD6402	Approved
0.7252	Intermediate Similarity	NPD6033	Approved
0.725	Intermediate Similarity	NPD5697	Approved
0.7213	Intermediate Similarity	NPD7290	Approved
0.7213	Intermediate Similarity	NPD6883	Approved
0.7213	Intermediate Similarity	NPD7102	Approved
0.719	Intermediate Similarity	NPD7320	Approved
0.7188	Intermediate Similarity	NPD8513	Phase 3
0.7188	Intermediate Similarity	NPD8517	Approved
0.7188	Intermediate Similarity	NPD8516	Approved
0.7188	Intermediate Similarity	NPD8515	Approved
0.7177	Intermediate Similarity	NPD8133	Approved
0.7154	Intermediate Similarity	NPD8130	Phase 1
0.7154	Intermediate Similarity	NPD6869	Approved
0.7154	Intermediate Similarity	NPD6617	Approved
0.7154	Intermediate Similarity	NPD6847	Approved
0.7131	Intermediate Similarity	NPD6013	Approved
0.7131	Intermediate Similarity	NPD6014	Approved
0.7131	Intermediate Similarity	NPD6012	Approved
0.7109	Intermediate Similarity	NPD8377	Approved
0.7109	Intermediate Similarity	NPD8294	Approved
0.7107	Intermediate Similarity	NPD5701	Approved
0.7077	Intermediate Similarity	NPD7604	Phase 2
0.7077	Intermediate Similarity	NPD6067	Discontinued
0.7073	Intermediate Similarity	NPD4634	Approved
0.7054	Intermediate Similarity	NPD8335	Approved
0.7054	Intermediate Similarity	NPD5983	Phase 2
0.7054	Intermediate Similarity	NPD8033	Approved
0.7054	Intermediate Similarity	NPD8380	Approved
0.7054	Intermediate Similarity	NPD8296	Approved
0.7054	Intermediate Similarity	NPD8379	Approved
0.7054	Intermediate Similarity	NPD8378	Approved
0.7049	Intermediate Similarity	NPD6011	Approved
0.7034	Intermediate Similarity	NPD4696	Approved
0.7034	Intermediate Similarity	NPD5285	Approved
0.7034	Intermediate Similarity	NPD5286	Approved
0.7031	Intermediate Similarity	NPD7516	Approved
0.7009	Intermediate Similarity	NPD7902	Approved
0.7009	Intermediate Similarity	NPD4755	Approved
0.697	Remote Similarity	NPD6336	Discontinued
0.6953	Remote Similarity	NPD7328	Approved
0.6953	Remote Similarity	NPD7327	Approved
0.6923	Remote Similarity	NPD5221	Approved
0.6923	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD4697	Phase 3
0.6923	Remote Similarity	NPD5222	Approved
0.6917	Remote Similarity	NPD4633	Approved
0.6917	Remote Similarity	NPD5224	Approved
0.6917	Remote Similarity	NPD5225	Approved
0.6917	Remote Similarity	NPD5226	Approved
0.6917	Remote Similarity	NPD5211	Phase 2
0.6897	Remote Similarity	NPD7748	Approved
0.6891	Remote Similarity	NPD4700	Approved
0.688	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.687	Remote Similarity	NPD7515	Phase 2
0.687	Remote Similarity	NPD6079	Approved
0.6864	Remote Similarity	NPD5173	Approved
0.686	Remote Similarity	NPD5174	Approved
0.686	Remote Similarity	NPD5175	Approved
0.6855	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD5328	Approved
0.6833	Remote Similarity	NPD5223	Approved
0.6803	Remote Similarity	NPD5141	Approved
0.68	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6797	Remote Similarity	NPD6274	Approved
0.6794	Remote Similarity	NPD6921	Approved
0.6774	Remote Similarity	NPD4730	Approved
0.6774	Remote Similarity	NPD4729	Approved
0.6769	Remote Similarity	NPD7101	Approved
0.6769	Remote Similarity	NPD7100	Approved
0.6752	Remote Similarity	NPD7900	Approved
0.6752	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6748	Remote Similarity	NPD6008	Approved
0.6748	Remote Similarity	NPD4767	Approved
0.6748	Remote Similarity	NPD4768	Approved
0.6746	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6744	Remote Similarity	NPD7115	Discovery
0.6726	Remote Similarity	NPD3618	Phase 1
0.6723	Remote Similarity	NPD6083	Phase 2
0.6723	Remote Similarity	NPD6084	Phase 2
0.6692	Remote Similarity	NPD6335	Approved
0.6667	Remote Similarity	NPD5248	Approved
0.6667	Remote Similarity	NPD5251	Approved
0.6667	Remote Similarity	NPD6868	Approved
0.6667	Remote Similarity	NPD5249	Phase 3
0.6667	Remote Similarity	NPD5247	Approved
0.6667	Remote Similarity	NPD5250	Approved
0.6642	Remote Similarity	NPD5956	Approved
0.664	Remote Similarity	NPD5128	Approved
0.6617	Remote Similarity	NPD8080	Discontinued
0.6615	Remote Similarity	NPD6317	Approved
0.661	Remote Similarity	NPD5282	Discontinued
0.6585	Remote Similarity	NPD4754	Approved
0.6565	Remote Similarity	NPD6313	Approved
0.6565	Remote Similarity	NPD6314	Approved
0.656	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6541	Remote Similarity	NPD6909	Approved
0.6541	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6541	Remote Similarity	NPD6908	Approved
0.6529	Remote Similarity	NPD4225	Approved
0.6529	Remote Similarity	NPD5696	Approved
0.6529	Remote Similarity	NPD7638	Approved
0.6525	Remote Similarity	NPD6399	Phase 3
0.6525	Remote Similarity	NPD8171	Discontinued
0.6522	Remote Similarity	NPD3573	Approved
0.6484	Remote Similarity	NPD5215	Approved
0.6484	Remote Similarity	NPD5216	Approved
0.6484	Remote Similarity	NPD5217	Approved
0.6475	Remote Similarity	NPD7640	Approved
0.6475	Remote Similarity	NPD7639	Approved
0.6475	Remote Similarity	NPD7260	Phase 2
0.6466	Remote Similarity	NPD6672	Approved
0.6466	Remote Similarity	NPD5737	Approved
0.6429	Remote Similarity	NPD6845	Suspended
0.6423	Remote Similarity	NPD8074	Phase 3
0.6418	Remote Similarity	NPD8274	Clinical (unspecified phase)
0.6417	Remote Similarity	NPD5695	Phase 3
0.6417	Remote Similarity	NPD5210	Approved
0.6417	Remote Similarity	NPD4629	Approved
0.641	Remote Similarity	NPD4753	Phase 2
0.641	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6406	Remote Similarity	NPD5169	Approved
0.6406	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6406	Remote Similarity	NPD5135	Approved
0.6387	Remote Similarity	NPD4202	Approved
0.6378	Remote Similarity	NPD5168	Approved
0.6357	Remote Similarity	NPD5127	Approved
0.6339	Remote Similarity	NPD4695	Discontinued
0.6316	Remote Similarity	NPD6110	Phase 1
0.6293	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6261	Remote Similarity	NPD4786	Approved
0.6261	Remote Similarity	NPD3133	Approved
0.6261	Remote Similarity	NPD3666	Approved
0.6261	Remote Similarity	NPD3665	Phase 1
0.6228	Remote Similarity	NPD3667	Approved
0.6212	Remote Similarity	NPD5167	Approved
0.6194	Remote Similarity	NPD7641	Discontinued
0.6186	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6183	Remote Similarity	NPD6053	Discontinued
0.617	Remote Similarity	NPD6914	Discontinued
0.6167	Remote Similarity	NPD8034	Phase 2
0.6167	Remote Similarity	NPD8035	Phase 2
0.6167	Remote Similarity	NPD6411	Approved
0.6161	Remote Similarity	NPD3617	Approved
0.6154	Remote Similarity	NPD7146	Approved
0.6154	Remote Similarity	NPD7521	Approved
0.6154	Remote Similarity	NPD7334	Approved
0.6154	Remote Similarity	NPD6409	Approved
0.6154	Remote Similarity	NPD5279	Phase 3
0.6154	Remote Similarity	NPD5330	Approved
0.6154	Remote Similarity	NPD6684	Approved
0.6148	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6143	Remote Similarity	NPD8336	Approved
0.6143	Remote Similarity	NPD8337	Approved
0.6138	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6134	Remote Similarity	NPD6673	Approved
0.6134	Remote Similarity	NPD6080	Approved
0.6134	Remote Similarity	NPD6904	Approved
0.6121	Remote Similarity	NPD7799	Discontinued
0.6119	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.6111	Remote Similarity	NPD7632	Discontinued
0.6106	Remote Similarity	NPD7645	Phase 2
0.6096	Remote Similarity	NPD6334	Approved
0.6096	Remote Similarity	NPD6333	Approved
0.6084	Remote Similarity	NPD8449	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