NPASS Compound

Structure

NPC139181 OpenBabel07101718312D 47 55 0 0 1 0 0 0 0 0999 V2000 -1.2202 2.7406 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6739 3.8917 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7543 3.0257 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2543 3.8917 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7847 1.7872 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6795 -1.7732 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3364 3.2007 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3883 2.3917 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5223 1.8917 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3883 5.3917 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5223 4.8917 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4013 1.0181 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5823 0.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7902 3.8917 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.7184 4.8917 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6562 4.3917 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4945 -1.4343 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8135 1.8271 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8079 3.3917 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.7184 3.8917 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.5878 0.8090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.3883 3.3917 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.6562 2.3917 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.2543 4.8917 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.9242 3.3917 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.1810 1.7226 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 7.8524 3.3917 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 6.9864 3.8917 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 6.9864 4.8917 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.9945 0.1045 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.2543 3.8917 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7902 1.8917 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.3035 -0.8465 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.9242 2.3917 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.5223 3.8917 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.6562 3.3917 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.9945 0.1045 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8079 2.3917 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 9.5844 3.3917 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.8524 2.3917 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.1203 3.3917 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.8524 5.3917 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.6855 -0.8465 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0582 3.8917 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.1203 5.3917 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 -2.9727 -0.1034 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 19 1 0 0 0 0 3 31 1 0 0 0 0 4 31 1 0 0 0 0 5 32 1 0 0 0 0 8 9 1 0 0 0 0 8 22 1 0 0 0 0 9 23 1 0 0 0 0 10 11 1 0 0 0 0 10 24 1 0 0 0 0 11 35 1 0 0 0 0 12 18 1 0 0 0 0 13 32 1 0 0 0 0 14 25 1 0 0 0 0 15 20 1 0 0 0 0 15 42 1 0 0 0 0 16 35 1 0 0 0 0 16 36 1 0 0 0 0 17 33 1 0 0 0 0 17 43 1 0 0 0 0 18 1 1 1 0 0 0 18 26 1 0 0 0 0 19 38 2 0 0 0 0 19 44 1 0 0 0 0 20 27 1 0 0 0 0 20 39 1 1 0 0 0 21 13 1 6 0 0 0 21 26 1 0 0 0 0 21 46 1 0 0 0 0 22 31 1 0 0 0 0 22 35 1 6 0 0 0 23 32 1 1 0 0 0 23 36 1 0 0 0 0 24 31 1 0 0 0 0 24 45 1 6 0 0 0 25 34 1 6 0 0 0 25 44 1 0 0 0 0 26 34 1 6 0 0 0 27 28 1 0 0 0 0 27 40 1 6 0 0 0 28 29 1 0 0 0 0 28 41 1 1 0 0 0 29 42 1 0 0 0 0 29 45 1 6 0 0 0 30 33 1 1 0 0 0 30 37 1 0 0 0 0 30 47 1 0 0 0 0 32 34 1 1 0 0 0 33 6 1 1 0 0 0 33 47 1 0 0 0 0 34 7 1 6 0 0 0 35 36 1 1 0 0 0 36 14 1 1 0 0 0 37 12 1 6 0 0 0 37 43 1 0 0 0 0 37 46 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	468.4
Volume:	531.553
LogP:	8.786
LogD:	5.982
LogS:	-7.199
# Rotatable Bonds:	6
TPSA:	26.3
# H-Bond Aceptor:	2
# H-Bond Donor:	0
# Rings:	5
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.298
Synthetic Accessibility Score:	5.398
Fsp3:	0.906
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.978
MDCK Permeability:	1.3362358004087582e-05
Pgp-inhibitor:	0.038
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.98
30% Bioavailability (F30%):	0.978

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.015
Plasma Protein Binding (PPB):	92.9035415649414%
Volume Distribution (VD):	1.346
Pgp-substrate:	1.4336216449737549%

ADMET: Metabolism

CYP1A2-inhibitor:	0.043
CYP1A2-substrate:	0.147
CYP2C19-inhibitor:	0.13
CYP2C19-substrate:	0.939
CYP2C9-inhibitor:	0.225
CYP2C9-substrate:	0.204
CYP2D6-inhibitor:	0.131
CYP2D6-substrate:	0.151
CYP3A4-inhibitor:	0.747
CYP3A4-substrate:	0.662

ADMET: Excretion

Clearance (CL):	4.999
Half-life (T1/2):	0.026

ADMET: Toxicity

hERG Blockers:	0.87
Human Hepatotoxicity (H-HT):	0.432
Drug-inuced Liver Injury (DILI):	0.697
AMES Toxicity:	0.001
Rat Oral Acute Toxicity:	0.081
Maximum Recommended Daily Dose:	0.389
Skin Sensitization:	0.959
Carcinogencity:	0.058
Eye Corrosion:	0.71
Eye Irritation:	0.435
Respiratory Toxicity:	0.781

Download Data

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

Natural Product: NPC139181

Natural Product ID:	NPC139181
*Common Name:**	GCMGJWLOGKSUGX-KKGXZNBCSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	GCMGJWLOGKSUGX-KKGXZNBCSA-N
Standard InCHI:	InChI=1S/C37H56O10/c1-18-12-37(30-33(6,47-30)17-43-37)46-21-13-32(5)23-9-8-22-31(3,4)24(45-29-28(41)27(40)20(39)15-42-29)10-11-35(22)16-36(23,35)14-25(44-19(2)38)34(32,7)26(18)21/h18,20-30,39-41H,8-17H2,1-7H3/t18-,20-,21+,22+,23+,24+,25-,26+,27+,28-,29+,30+,32+,33+,34-,35-,36+,37-/m1/s1
SMILES:	C[C@@H]1C[C@]2([C@@H]3[C@](C)(CO2)O3)O[C@H]2C[C@@]3(C)[C@@H]4CC[C@H]5C(C)(C)[C@H](CC[C@]65C[C@@]46C[C@H]([C@]3(C)[C@@H]12)OC(=O)C)O[C@H]1[C@@H]([C@H]([C@@H](CO1)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL387163
PubChem CID:	44418833
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0002321] Cycloartanols and derivatives

*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
NPO26366	Actaea pachypoda	Species	Ranunculaceae	Eukaryota	roots	n.a.	n.a.	PMID[17253859]
NPO31564	Cimicifuga foetida	n.a.	n.a.	n.a.	n.a.	aerial part	n.a.	PMID[19280146]
NPO31564	Cimicifuga foetida	n.a.	n.a.	n.a.	rhizomes	n.a.	n.a.	PMID[25136911]
NPO31564	Cimicifuga foetida	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[HerDing]
NPO31564	Cimicifuga foetida	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO26366	Actaea pachypoda	Species	Ranunculaceae	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	5

Activity Type	# Activity
Cell Line	2
NON-MOLECULAR	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT83	Cell Line	MCF7	Homo sapiens	IC50	>	10000.0	nM	PMID[522784]
NPT165	Cell Line	HeLa	Homo sapiens	IC50	>	10000.0	nM	PMID[522784]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	10000.0	nM	PMID[522784]

☑ 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 NPC139181 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	603
0.1-0.2	5102
0.2-0.3	14259
0.3-0.4	9963
0.4-0.5	5735
0.5-0.6	3788
0.6-0.7	2108
0.7-0.8	875
0.8-0.85	105
0.85-0.9	127
0.9-0.95	15
0.95-1	17

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC97260
1.0	High Similarity	NPC476837
0.9789	High Similarity	NPC476512
0.9789	High Similarity	NPC108227
0.9789	High Similarity	NPC472081
0.9688	High Similarity	NPC114700
0.9688	High Similarity	NPC134967
0.9688	High Similarity	NPC310138
0.9688	High Similarity	NPC470029
0.9684	High Similarity	NPC470030
0.9381	High Similarity	NPC475574
0.9381	High Similarity	NPC476839
0.9381	High Similarity	NPC476838
0.9368	High Similarity	NPC252056
0.9368	High Similarity	NPC142264
0.9368	High Similarity	NPC238796
0.9368	High Similarity	NPC237071
0.9368	High Similarity	NPC476510
0.9368	High Similarity	NPC203434
0.9271	High Similarity	NPC475207
0.9271	High Similarity	NPC470028
0.9271	High Similarity	NPC233649
0.9167	High Similarity	NPC156377
0.9167	High Similarity	NPC296936
0.9158	High Similarity	NPC252253
0.9158	High Similarity	NPC151214
0.9158	High Similarity	NPC45959
0.9158	High Similarity	NPC175
0.9158	High Similarity	NPC30687
0.9158	High Similarity	NPC191915
0.9072	High Similarity	NPC470591
0.9062	High Similarity	NPC473064
0.9062	High Similarity	NPC94582
0.9062	High Similarity	NPC473067
0.9062	High Similarity	NPC473065
0.9062	High Similarity	NPC57964
0.9053	High Similarity	NPC144790
0.9053	High Similarity	NPC88962
0.9053	High Similarity	NPC473726
0.9053	High Similarity	NPC149400
0.8969	High Similarity	NPC139271
0.8969	High Similarity	NPC304011
0.8958	High Similarity	NPC473851
0.8958	High Similarity	NPC312678
0.8958	High Similarity	NPC291547
0.8958	High Similarity	NPC131693
0.8958	High Similarity	NPC475436
0.8958	High Similarity	NPC174024
0.8958	High Similarity	NPC253268
0.8958	High Similarity	NPC473774
0.8958	High Similarity	NPC179859
0.8958	High Similarity	NPC24960
0.8947	High Similarity	NPC229801
0.8947	High Similarity	NPC307167
0.8947	High Similarity	NPC210759
0.8878	High Similarity	NPC477222
0.8878	High Similarity	NPC477223
0.8878	High Similarity	NPC210157
0.8866	High Similarity	NPC474399
0.8854	High Similarity	NPC141769
0.8854	High Similarity	NPC297348
0.8854	High Similarity	NPC234352
0.8854	High Similarity	NPC249204
0.8854	High Similarity	NPC250393
0.8854	High Similarity	NPC48339
0.8854	High Similarity	NPC325828
0.8854	High Similarity	NPC311246
0.8854	High Similarity	NPC477547
0.8854	High Similarity	NPC167644
0.8854	High Similarity	NPC177834
0.8854	High Similarity	NPC477451
0.8842	High Similarity	NPC473542
0.8842	High Similarity	NPC65550
0.8785	High Similarity	NPC212660
0.8776	High Similarity	NPC121453
0.8763	High Similarity	NPC217205
0.8763	High Similarity	NPC291203
0.8763	High Similarity	NPC113500
0.8763	High Similarity	NPC305418
0.8763	High Similarity	NPC471464
0.8763	High Similarity	NPC294686
0.8763	High Similarity	NPC477224
0.8763	High Similarity	NPC222731
0.8763	High Similarity	NPC3538
0.8763	High Similarity	NPC264101
0.8763	High Similarity	NPC309866
0.875	High Similarity	NPC149966
0.875	High Similarity	NPC473066
0.875	High Similarity	NPC59006
0.875	High Similarity	NPC204881
0.875	High Similarity	NPC473830
0.875	High Similarity	NPC5632
0.8737	High Similarity	NPC82955
0.8737	High Similarity	NPC131466
0.8687	High Similarity	NPC274200
0.8687	High Similarity	NPC476112
0.8687	High Similarity	NPC307534
0.8673	High Similarity	NPC206003
0.8673	High Similarity	NPC475351
0.8673	High Similarity	NPC19400
0.8673	High Similarity	NPC473610
0.8673	High Similarity	NPC107962
0.8673	High Similarity	NPC211354
0.8673	High Similarity	NPC92196
0.8673	High Similarity	NPC6295
0.8673	High Similarity	NPC107188
0.8673	High Similarity	NPC473727
0.866	High Similarity	NPC172838
0.866	High Similarity	NPC137004
0.8654	High Similarity	NPC472079
0.8646	High Similarity	NPC279329
0.8632	High Similarity	NPC281004
0.86	High Similarity	NPC473518
0.86	High Similarity	NPC473616
0.86	High Similarity	NPC292775
0.8586	High Similarity	NPC473601
0.8586	High Similarity	NPC103616
0.8586	High Similarity	NPC475643
0.8586	High Similarity	NPC128572
0.8586	High Similarity	NPC195297
0.8586	High Similarity	NPC287483
0.8586	High Similarity	NPC232037
0.8586	High Similarity	NPC284104
0.8586	High Similarity	NPC84111
0.8586	High Similarity	NPC116756
0.8586	High Similarity	NPC475625
0.8586	High Similarity	NPC470866
0.8586	High Similarity	NPC132080
0.8586	High Similarity	NPC470864
0.8586	High Similarity	NPC160426
0.8586	High Similarity	NPC470865
0.8586	High Similarity	NPC30856
0.8586	High Similarity	NPC470863
0.8586	High Similarity	NPC184617
0.8586	High Similarity	NPC98018
0.8586	High Similarity	NPC97700
0.8571	High Similarity	NPC227879
0.8571	High Similarity	NPC208333
0.8557	High Similarity	NPC293609
0.8557	High Similarity	NPC36372
0.8542	High Similarity	NPC473472
0.8542	High Similarity	NPC20822
0.8542	High Similarity	NPC228059
0.8542	High Similarity	NPC102725
0.8526	High Similarity	NPC140446
0.8526	High Similarity	NPC43912
0.8515	High Similarity	NPC41843
0.8505	High Similarity	NPC477489
0.85	High Similarity	NPC470862
0.85	High Similarity	NPC470861
0.85	High Similarity	NPC83137
0.85	High Similarity	NPC303069
0.85	High Similarity	NPC51520
0.85	High Similarity	NPC232611
0.85	High Similarity	NPC115165
0.8485	Intermediate Similarity	NPC21897
0.8469	Intermediate Similarity	NPC277774
0.8469	Intermediate Similarity	NPC211845
0.8469	Intermediate Similarity	NPC256104
0.8469	Intermediate Similarity	NPC122083
0.8469	Intermediate Similarity	NPC182740
0.8454	Intermediate Similarity	NPC223143
0.8431	Intermediate Similarity	NPC477172
0.8416	Intermediate Similarity	NPC471374
0.8416	Intermediate Similarity	NPC291548
0.8416	Intermediate Similarity	NPC471375
0.8416	Intermediate Similarity	NPC473638
0.8416	Intermediate Similarity	NPC209798
0.8384	Intermediate Similarity	NPC473503
0.8367	Intermediate Similarity	NPC476668
0.8367	Intermediate Similarity	NPC473637
0.8333	Intermediate Similarity	NPC471426
0.8333	Intermediate Similarity	NPC471428
0.8333	Intermediate Similarity	NPC20028
0.8333	Intermediate Similarity	NPC51579
0.8333	Intermediate Similarity	NPC471427
0.8316	Intermediate Similarity	NPC290612
0.83	Intermediate Similarity	NPC477494
0.83	Intermediate Similarity	NPC215570
0.83	Intermediate Similarity	NPC469710
0.8286	Intermediate Similarity	NPC215408
0.8283	Intermediate Similarity	NPC476669
0.8252	Intermediate Similarity	NPC477225
0.8247	Intermediate Similarity	NPC470872
0.8241	Intermediate Similarity	NPC473062
0.8241	Intermediate Similarity	NPC469824
0.8229	Intermediate Similarity	NPC477283
0.8229	Intermediate Similarity	NPC471410
0.8229	Intermediate Similarity	NPC155531
0.8229	Intermediate Similarity	NPC215968
0.8229	Intermediate Similarity	NPC471411
0.8224	Intermediate Similarity	NPC476835
0.8218	Intermediate Similarity	NPC473287
0.8211	Intermediate Similarity	NPC474156
0.8208	Intermediate Similarity	NPC203974
0.82	Intermediate Similarity	NPC475325
0.8198	Intermediate Similarity	NPC179429
0.819	Intermediate Similarity	NPC469827
0.8182	Intermediate Similarity	NPC79193
0.8173	Intermediate Similarity	NPC310031

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 NPC139181 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	604
0.1-0.2	4594
0.2-0.3	2789
0.3-0.4	639
0.4-0.5	326
0.5-0.6	157
0.6-0.7	26
0.7-0.8	13
0.8-0.85	1
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8854	High Similarity	NPD8171	Discontinued
0.8365	Intermediate Similarity	NPD8170	Clinical (unspecified phase)
0.7826	Intermediate Similarity	NPD8377	Approved
0.7826	Intermediate Similarity	NPD8294	Approved
0.7789	Intermediate Similarity	NPD6928	Phase 2
0.7759	Intermediate Similarity	NPD8378	Approved
0.7759	Intermediate Similarity	NPD8033	Approved
0.7759	Intermediate Similarity	NPD8296	Approved
0.7759	Intermediate Similarity	NPD8380	Approved
0.7759	Intermediate Similarity	NPD8335	Approved
0.7759	Intermediate Similarity	NPD8379	Approved
0.7611	Intermediate Similarity	NPD8133	Approved
0.75	Intermediate Similarity	NPD7328	Approved
0.75	Intermediate Similarity	NPD7327	Approved
0.7436	Intermediate Similarity	NPD7516	Approved
0.7073	Intermediate Similarity	NPD7507	Approved
0.7025	Intermediate Similarity	NPD7503	Approved
0.6957	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD7991	Discontinued
0.6905	Remote Similarity	NPD7319	Approved
0.6863	Remote Similarity	NPD3669	Approved
0.6863	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.6833	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6825	Remote Similarity	NPD7736	Approved
0.675	Remote Similarity	NPD6940	Discontinued
0.6737	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.67	Remote Similarity	NPD6697	Approved
0.67	Remote Similarity	NPD6114	Approved
0.67	Remote Similarity	NPD6115	Approved
0.67	Remote Similarity	NPD6118	Approved
0.6638	Remote Similarity	NPD6412	Phase 2
0.6633	Remote Similarity	NPD1811	Approved
0.6633	Remote Similarity	NPD1810	Approved
0.6614	Remote Similarity	NPD8293	Discontinued
0.66	Remote Similarity	NPD6116	Phase 1
0.6508	Remote Similarity	NPD8328	Phase 3
0.65	Remote Similarity	NPD6117	Approved
0.6491	Remote Similarity	NPD1700	Approved
0.6429	Remote Similarity	NPD6370	Approved
0.6328	Remote Similarity	NPD7492	Approved
0.6327	Remote Similarity	NPD2687	Approved
0.6327	Remote Similarity	NPD7532	Clinical (unspecified phase)
0.6327	Remote Similarity	NPD2254	Approved
0.6327	Remote Similarity	NPD2686	Approved
0.63	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6279	Remote Similarity	NPD6616	Approved
0.627	Remote Similarity	NPD6054	Approved
0.627	Remote Similarity	NPD6059	Approved
0.6241	Remote Similarity	NPD8449	Approved
0.6241	Remote Similarity	NPD7625	Phase 1
0.6238	Remote Similarity	NPD3702	Approved
0.6231	Remote Similarity	NPD7078	Approved
0.6216	Remote Similarity	NPD8035	Phase 2
0.6216	Remote Similarity	NPD8034	Phase 2
0.6194	Remote Similarity	NPD8450	Suspended
0.619	Remote Similarity	NPD1780	Approved
0.619	Remote Similarity	NPD1779	Approved
0.6186	Remote Similarity	NPD4056	Clinical (unspecified phase)
0.6186	Remote Similarity	NPD4057	Clinical (unspecified phase)
0.6167	Remote Similarity	NPD8174	Phase 2
0.6167	Remote Similarity	NPD6686	Approved
0.6162	Remote Similarity	NPD4787	Phase 1
0.6116	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6098	Remote Similarity	NPD6882	Approved
0.6098	Remote Similarity	NPD8297	Approved
0.6094	Remote Similarity	NPD6016	Approved
0.6094	Remote Similarity	NPD6015	Approved
0.6047	Remote Similarity	NPD5988	Approved
0.6034	Remote Similarity	NPD7638	Approved
0.6032	Remote Similarity	NPD6009	Approved
0.6016	Remote Similarity	NPD6319	Approved
0.6	Remote Similarity	NPD6067	Discontinued
0.6	Remote Similarity	NPD6008	Approved
0.5983	Remote Similarity	NPD7639	Approved
0.5983	Remote Similarity	NPD7640	Approved
0.5969	Remote Similarity	NPD8517	Approved
0.5969	Remote Similarity	NPD8513	Phase 3
0.5969	Remote Similarity	NPD8515	Approved
0.5969	Remote Similarity	NPD8516	Approved
0.5963	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.5941	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.5941	Remote Similarity	NPD5777	Approved
0.5941	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.5935	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.5922	Remote Similarity	NPD3703	Phase 2
0.592	Remote Similarity	NPD4632	Approved
0.5902	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.5902	Remote Similarity	NPD7320	Approved
0.5882	Remote Similarity	NPD7632	Discontinued
0.5878	Remote Similarity	NPD7604	Phase 2
0.5876	Remote Similarity	NPD371	Approved
0.5868	Remote Similarity	NPD7128	Approved
0.5868	Remote Similarity	NPD6402	Approved
0.5868	Remote Similarity	NPD6675	Approved
0.5868	Remote Similarity	NPD5739	Approved
0.5854	Remote Similarity	NPD6372	Approved
0.5854	Remote Similarity	NPD6373	Approved
0.5842	Remote Similarity	NPD4244	Approved
0.5842	Remote Similarity	NPD4245	Approved
0.5821	Remote Similarity	NPD6033	Approved
0.582	Remote Similarity	NPD7646	Clinical (unspecified phase)
0.5794	Remote Similarity	NPD7525	Registered
0.5781	Remote Similarity	NPD7115	Discovery
0.5772	Remote Similarity	NPD6881	Approved
0.5772	Remote Similarity	NPD6899	Approved
0.576	Remote Similarity	NPD6650	Approved
0.576	Remote Similarity	NPD6649	Approved
0.576	Remote Similarity	NPD8130	Phase 1
0.5743	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.5743	Remote Similarity	NPD3698	Phase 2
0.5743	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD8418	Phase 2
0.5691	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.5691	Remote Similarity	NPD5701	Approved
0.5691	Remote Similarity	NPD5697	Approved
0.568	Remote Similarity	NPD6883	Approved
0.568	Remote Similarity	NPD7102	Approved
0.568	Remote Similarity	NPD7290	Approved
0.5644	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.5644	Remote Similarity	NPD5360	Phase 3
0.5641	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.5635	Remote Similarity	NPD6847	Approved
0.5635	Remote Similarity	NPD6617	Approved
0.5635	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.5635	Remote Similarity	NPD6869	Approved
0.5631	Remote Similarity	NPD6081	Approved
0.562	Remote Similarity	NPD8084	Approved
0.562	Remote Similarity	NPD8138	Approved
0.562	Remote Similarity	NPD8139	Approved
0.562	Remote Similarity	NPD8086	Approved
0.562	Remote Similarity	NPD8082	Approved
0.562	Remote Similarity	NPD8083	Approved
0.562	Remote Similarity	NPD8085	Approved
0.5606	Remote Similarity	NPD5983	Phase 2
0.56	Remote Similarity	NPD6012	Approved
0.56	Remote Similarity	NPD6013	Approved
0.56	Remote Similarity	NPD6014	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