NPASS Compound

Structure

CID54909 OpenBabel06191715392D 38 42 0 0 1 0 0 0 0 0999 V2000 5.0753 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5377 5.3721 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5144 1.4651 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0260 0.6192 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.9535 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8459 -1.4651 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.9767 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8719 0.8459 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6918 0.9767 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8459 1.4651 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2294 -1.4651 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6918 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8459 -0.4884 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3835 -1.9535 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8459 -1.4651 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6918 -1.9535 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8459 2.4419 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2294 -0.4884 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5377 4.3953 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6918 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6918 2.9302 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.6918 0.9767 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 0.9767 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5377 -0.4884 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5377 2.4419 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5377 -2.4419 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5377 1.4651 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8459 1.4651 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8459 -0.4884 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.3835 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5377 -1.4651 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.3835 3.9070 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3835 2.9302 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6918 -2.9302 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3835 -2.9302 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.8952 0.8459 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6918 3.9070 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 18 1 0 0 0 0 2 19 1 0 0 0 0 3 27 1 0 0 0 0 4 27 1 0 0 0 0 6 29 1 0 0 0 0 9 10 1 0 0 0 0 9 20 2 0 0 0 0 10 23 1 0 0 0 0 11 14 1 0 0 0 0 11 18 1 0 0 0 0 12 13 1 0 0 0 0 12 22 1 0 0 0 0 13 30 1 0 0 0 0 14 32 1 0 0 0 0 15 16 1 0 0 0 0 15 29 1 0 0 0 0 16 32 1 0 0 0 0 17 21 1 0 0 0 0 17 28 1 0 0 0 0 18 31 1 6 0 0 0 19 33 2 0 0 0 0 19 38 1 0 0 0 0 20 24 1 0 0 0 0 20 29 1 0 0 0 0 21 25 1 0 0 0 0 21 38 1 6 0 0 0 22 27 1 0 0 0 0 22 28 1 1 0 0 0 23 28 1 1 0 0 0 23 30 1 0 0 0 0 24 31 1 6 0 0 0 24 32 1 0 0 0 0 25 27 1 0 0 0 0 25 34 1 1 0 0 0 26 35 2 0 0 0 0 26 36 1 0 0 0 0 28 5 1 1 0 0 0 29 30 1 1 0 0 0 30 7 1 1 0 0 0 31 8 1 1 0 0 0 31 37 1 0 0 0 0 32 26 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	530.36
Volume:	564.078
LogP:	4.759
LogD:	4.292
LogS:	-4.192
# Rotatable Bonds:	3
TPSA:	104.06
# H-Bond Aceptor:	6
# H-Bond Donor:	3
# Rings:	5
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.31
Synthetic Accessibility Score:	5.101
Fsp3:	0.875
Lipinski Rule-of-5:	Accepted
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:	-5.503
MDCK Permeability:	1.6287733160424978e-05
Pgp-inhibitor:	0.054
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.008
20% Bioavailability (F20%):	0.034
30% Bioavailability (F30%):	0.865

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.051
Plasma Protein Binding (PPB):	92.9689712524414%
Volume Distribution (VD):	0.679
Pgp-substrate:	4.617470741271973%

ADMET: Metabolism

CYP1A2-inhibitor:	0.006
CYP1A2-substrate:	0.143
CYP2C19-inhibitor:	0.009
CYP2C19-substrate:	0.816
CYP2C9-inhibitor:	0.139
CYP2C9-substrate:	0.561
CYP2D6-inhibitor:	0.005
CYP2D6-substrate:	0.105
CYP3A4-inhibitor:	0.219
CYP3A4-substrate:	0.307

ADMET: Excretion

Clearance (CL):	1.795
Half-life (T1/2):	0.239

ADMET: Toxicity

hERG Blockers:	0.004
Human Hepatotoxicity (H-HT):	0.209
Drug-inuced Liver Injury (DILI):	0.039
AMES Toxicity:	0.007
Rat Oral Acute Toxicity:	0.73
Maximum Recommended Daily Dose:	0.89
Skin Sensitization:	0.168
Carcinogencity:	0.019
Eye Corrosion:	0.123
Eye Irritation:	0.105
Respiratory Toxicity:	0.983

Download Data

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

Natural Product: NPC54909

Natural Product ID:	NPC54909
*Common Name:**	2 Alpha-Acetyl Tomentic Acid
IUPAC Name:	(1R,2R,4aS,6aR,6aS,6bR,8aR,10R,11R,12aR,14bS)-11-acetyloxy-1,10-dihydroxy-1,2,6a,6b,9,9,12a-heptamethyl-2,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylic acid
Synonyms:	2 Alpha-Acetyl Tomentic Acid
Standard InCHIKey:	HHDNTTOUNUERTJ-BGJCYSRJSA-N
Standard InCHI:	InChI=1S/C32H50O6/c1-18-11-14-32(26(35)36)16-15-29(6)20(24(32)31(18,8)37)9-10-23-28(5)17-21(38-19(2)33)25(34)27(3,4)22(28)12-13-30(23,29)7/h9,18,21-25,34,37H,10-17H2,1-8H3,(H,35,36)/t18-,21-,22+,23-,24-,25+,28+,29-,30-,31-,32+/m1/s1
SMILES:	C[C@@H]1CC[C@@]2(CC[C@]3(C)C(=CC[C@@H]4[C@@]5(C)C[C@H]([C@@H](C(C)(C)[C@@H]5CC[C@@]34C)O)OC(=O)C)[C@@H]2[C@]1(C)O)C(=O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL439053
PubChem CID:	44436803
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids

*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
NPO20072	Verbascum dudleyanum	Species	Scrophulariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5696	Premna fulva	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6660	Cecropia lyratiloba	Species	Urticaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1029	Vernonia jalcana	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
IC50	10

Activity Type	# Activity
Cell Line	7
NON-MOLECULAR	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT111	Cell Line	K562	Homo sapiens	IC50	=	38350.0	nM	PMID[479618]
NPT1215	Cell Line	8505C	Homo sapiens	IC50	>	30000.0	nM	PMID[479619]
NPT179	Cell Line	A2780	Homo sapiens	IC50	=	24300.0	nM	PMID[479619]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	30000.0	nM	PMID[479619]
NPT579	Cell Line	DLD-1	Homo sapiens	IC50	>	30000.0	nM	PMID[479619]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	25300.0	nM	PMID[479619]
NPT886	Cell Line	NIH3T3	Mus musculus	IC50	>	30000.0	nM	PMID[479619]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	41380.0	nM	PMID[479618]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	30000.0	nM	PMID[479619]

☑ 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 NPC54909 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	232
0.1-0.2	1417
0.2-0.3	4474
0.3-0.4	11335
0.4-0.5	11019
0.5-0.6	5822
0.6-0.7	5230
0.7-0.8	2378
0.8-0.85	453
0.85-0.9	237
0.9-0.95	88
0.95-1	12

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC233012
0.9677	High Similarity	NPC255589
0.9677	High Similarity	NPC259788
0.957	High Similarity	NPC259733
0.957	High Similarity	NPC207922
0.957	High Similarity	NPC327179
0.957	High Similarity	NPC158371
0.957	High Similarity	NPC230151
0.9468	High Similarity	NPC247139
0.9468	High Similarity	NPC9613
0.9462	High Similarity	NPC96916
0.9362	High Similarity	NPC204961
0.9362	High Similarity	NPC173744
0.9362	High Similarity	NPC73004
0.9355	High Similarity	NPC296164
0.9271	High Similarity	NPC35239
0.9263	High Similarity	NPC43686
0.9247	High Similarity	NPC136313
0.9247	High Similarity	NPC118519
0.9247	High Similarity	NPC202728
0.9247	High Similarity	NPC74855
0.9247	High Similarity	NPC158059
0.9247	High Similarity	NPC307335
0.9247	High Similarity	NPC275809
0.9192	High Similarity	NPC477877
0.9175	High Similarity	NPC256247
0.9167	High Similarity	NPC29765
0.9167	High Similarity	NPC271614
0.9167	High Similarity	NPC111214
0.9149	High Similarity	NPC145667
0.9149	High Similarity	NPC114159
0.9149	High Similarity	NPC88116
0.9149	High Similarity	NPC282395
0.9149	High Similarity	NPC191412
0.9149	High Similarity	NPC263548
0.9149	High Similarity	NPC32407
0.9149	High Similarity	NPC299996
0.9149	High Similarity	NPC6818
0.9149	High Similarity	NPC231063
0.9149	High Similarity	NPC20235
0.914	High Similarity	NPC187722
0.914	High Similarity	NPC306541
0.914	High Similarity	NPC300351
0.914	High Similarity	NPC472149
0.914	High Similarity	NPC77099
0.914	High Similarity	NPC235884
0.914	High Similarity	NPC60755
0.914	High Similarity	NPC71074
0.914	High Similarity	NPC84319
0.914	High Similarity	NPC470590
0.914	High Similarity	NPC25299
0.914	High Similarity	NPC52021
0.914	High Similarity	NPC285184
0.9072	High Similarity	NPC476195
0.9062	High Similarity	NPC203343
0.9062	High Similarity	NPC106112
0.9062	High Similarity	NPC261935
0.9062	High Similarity	NPC312075
0.9053	High Similarity	NPC32118
0.9043	High Similarity	NPC474806
0.9043	High Similarity	NPC229281
0.9043	High Similarity	NPC86368
0.9043	High Similarity	NPC133579
0.9032	High Similarity	NPC474728
0.9032	High Similarity	NPC227467
0.9032	High Similarity	NPC49320
0.9032	High Similarity	NPC273621
0.9032	High Similarity	NPC18872
0.9032	High Similarity	NPC120968
0.9032	High Similarity	NPC290614
0.9032	High Similarity	NPC477872
0.9032	High Similarity	NPC113989
0.9032	High Similarity	NPC210037
0.9032	High Similarity	NPC7260
0.9032	High Similarity	NPC120840
0.898	High Similarity	NPC476132
0.8969	High Similarity	NPC260149
0.8969	High Similarity	NPC58942
0.8969	High Similarity	NPC188833
0.8958	High Similarity	NPC62516
0.8958	High Similarity	NPC19376
0.8958	High Similarity	NPC25848
0.8958	High Similarity	NPC116457
0.8958	High Similarity	NPC307282
0.8958	High Similarity	NPC305464
0.8958	High Similarity	NPC157113
0.8958	High Similarity	NPC201657
0.8958	High Similarity	NPC132824
0.8947	High Similarity	NPC215700
0.8947	High Similarity	NPC87095
0.8942	High Similarity	NPC271138
0.8942	High Similarity	NPC269315
0.8936	High Similarity	NPC38754
0.8936	High Similarity	NPC105189
0.8925	High Similarity	NPC470588
0.8925	High Similarity	NPC25906
0.8925	High Similarity	NPC274330
0.8925	High Similarity	NPC30522
0.8925	High Similarity	NPC64872
0.8925	High Similarity	NPC198664
0.8925	High Similarity	NPC290972
0.8925	High Similarity	NPC143232
0.8911	High Similarity	NPC301666
0.89	High Similarity	NPC284865
0.8866	High Similarity	NPC187933
0.8854	High Similarity	NPC198245
0.8854	High Similarity	NPC53565
0.8854	High Similarity	NPC474727
0.8854	High Similarity	NPC195715
0.8846	High Similarity	NPC46388
0.8846	High Similarity	NPC37739
0.8846	High Similarity	NPC116794
0.8842	High Similarity	NPC63118
0.8842	High Similarity	NPC118490
0.8842	High Similarity	NPC49776
0.8842	High Similarity	NPC474436
0.883	High Similarity	NPC291028
0.883	High Similarity	NPC130278
0.883	High Similarity	NPC111110
0.883	High Similarity	NPC193750
0.883	High Similarity	NPC126369
0.883	High Similarity	NPC470589
0.8817	High Similarity	NPC290690
0.8817	High Similarity	NPC181225
0.8817	High Similarity	NPC246708
0.8817	High Similarity	NPC470629
0.8817	High Similarity	NPC17733
0.8817	High Similarity	NPC182797
0.8817	High Similarity	NPC473242
0.8817	High Similarity	NPC474512
0.8817	High Similarity	NPC52169
0.8817	High Similarity	NPC40552
0.8776	High Similarity	NPC164349
0.8776	High Similarity	NPC477876
0.8776	High Similarity	NPC471966
0.8776	High Similarity	NPC174663
0.8776	High Similarity	NPC477875
0.8763	High Similarity	NPC88847
0.8762	High Similarity	NPC189884
0.8762	High Similarity	NPC204458
0.8762	High Similarity	NPC47063
0.8762	High Similarity	NPC138334
0.875	High Similarity	NPC148964
0.875	High Similarity	NPC60692
0.875	High Similarity	NPC78580
0.875	High Similarity	NPC191763
0.875	High Similarity	NPC74751
0.875	High Similarity	NPC23621
0.875	High Similarity	NPC184006
0.875	High Similarity	NPC188102
0.8738	High Similarity	NPC127853
0.8738	High Similarity	NPC310546
0.8725	High Similarity	NPC283849
0.8723	High Similarity	NPC121798
0.8723	High Similarity	NPC127689
0.8723	High Similarity	NPC61543
0.8723	High Similarity	NPC263393
0.8723	High Similarity	NPC234346
0.8723	High Similarity	NPC293048
0.8723	High Similarity	NPC225585
0.8723	High Similarity	NPC270768
0.8723	High Similarity	NPC130520
0.8723	High Similarity	NPC59263
0.871	High Similarity	NPC293564
0.871	High Similarity	NPC477926
0.871	High Similarity	NPC171203
0.871	High Similarity	NPC18064
0.871	High Similarity	NPC68160
0.871	High Similarity	NPC142415
0.871	High Similarity	NPC307426
0.871	High Similarity	NPC98442
0.871	High Similarity	NPC242468
0.871	High Similarity	NPC130577
0.871	High Similarity	NPC51700
0.871	High Similarity	NPC88716
0.871	High Similarity	NPC162107
0.871	High Similarity	NPC46912
0.871	High Similarity	NPC102683
0.8679	High Similarity	NPC475633
0.8673	High Similarity	NPC476878
0.8673	High Similarity	NPC158347
0.8673	High Similarity	NPC476879
0.8667	High Similarity	NPC128925
0.8667	High Similarity	NPC256798
0.866	High Similarity	NPC290481
0.866	High Similarity	NPC23241
0.866	High Similarity	NPC473240
0.866	High Similarity	NPC83693
0.8654	High Similarity	NPC102914
0.8654	High Similarity	NPC199457
0.8654	High Similarity	NPC75747
0.8654	High Similarity	NPC68419
0.8654	High Similarity	NPC108709
0.8654	High Similarity	NPC7870
0.8654	High Similarity	NPC110139
0.8654	High Similarity	NPC274507
0.8646	High Similarity	NPC214756
0.8646	High Similarity	NPC272075
0.8646	High Similarity	NPC295643
0.8641	High Similarity	NPC476123

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 NPC54909 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	206
0.1-0.2	1686
0.2-0.3	3747
0.3-0.4	2306
0.4-0.5	720
0.5-0.6	250
0.6-0.7	188
0.7-0.8	40
0.8-0.85	3
0.85-0.9	4
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8866	High Similarity	NPD7902	Approved
0.875	High Similarity	NPD7748	Approved
0.8557	High Similarity	NPD7900	Approved
0.8557	High Similarity	NPD7901	Clinical (unspecified phase)
0.8542	High Similarity	NPD7515	Phase 2
0.8163	Intermediate Similarity	NPD8035	Phase 2
0.8163	Intermediate Similarity	NPD8034	Phase 2
0.8081	Intermediate Similarity	NPD6399	Phase 3
0.8037	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7857	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7759	Intermediate Similarity	NPD8328	Phase 3
0.7732	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7699	Intermediate Similarity	NPD7115	Discovery
0.766	Intermediate Similarity	NPD7645	Phase 2
0.7658	Intermediate Similarity	NPD8297	Approved
0.7593	Intermediate Similarity	NPD5739	Approved
0.7593	Intermediate Similarity	NPD6675	Approved
0.7593	Intermediate Similarity	NPD7128	Approved
0.7593	Intermediate Similarity	NPD6402	Approved
0.7545	Intermediate Similarity	NPD6372	Approved
0.7545	Intermediate Similarity	NPD6373	Approved
0.7475	Intermediate Similarity	NPD3618	Phase 1
0.7455	Intermediate Similarity	NPD7320	Approved
0.7455	Intermediate Similarity	NPD6899	Approved
0.7455	Intermediate Similarity	NPD6881	Approved
0.7449	Intermediate Similarity	NPD4786	Approved
0.7423	Intermediate Similarity	NPD3667	Approved
0.7411	Intermediate Similarity	NPD8130	Phase 1
0.7411	Intermediate Similarity	NPD6650	Approved
0.7411	Intermediate Similarity	NPD6649	Approved
0.7387	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7364	Intermediate Similarity	NPD5701	Approved
0.7364	Intermediate Similarity	NPD5697	Approved
0.7358	Intermediate Similarity	NPD4225	Approved
0.7358	Intermediate Similarity	NPD7638	Approved
0.7327	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7321	Intermediate Similarity	NPD7102	Approved
0.7321	Intermediate Similarity	NPD6883	Approved
0.7321	Intermediate Similarity	NPD7290	Approved
0.7297	Intermediate Similarity	NPD6011	Approved
0.7297	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.729	Intermediate Similarity	NPD7640	Approved
0.729	Intermediate Similarity	NPD7639	Approved
0.7282	Intermediate Similarity	NPD6411	Approved
0.7281	Intermediate Similarity	NPD8133	Approved
0.7281	Intermediate Similarity	NPD4632	Approved
0.7264	Intermediate Similarity	NPD6083	Phase 2
0.7264	Intermediate Similarity	NPD6084	Phase 2
0.7257	Intermediate Similarity	NPD6869	Approved
0.7257	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7257	Intermediate Similarity	NPD6617	Approved
0.7257	Intermediate Similarity	NPD6847	Approved
0.7255	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.7255	Intermediate Similarity	NPD5328	Approved
0.7232	Intermediate Similarity	NPD6014	Approved
0.7232	Intermediate Similarity	NPD6013	Approved
0.7232	Intermediate Similarity	NPD6012	Approved
0.7228	Intermediate Similarity	NPD3573	Approved
0.7216	Intermediate Similarity	NPD7525	Registered
0.7212	Intermediate Similarity	NPD4202	Approved
0.7207	Intermediate Similarity	NPD6412	Phase 2
0.7193	Intermediate Similarity	NPD6882	Approved
0.7168	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7129	Intermediate Similarity	NPD7521	Approved
0.7129	Intermediate Similarity	NPD7334	Approved
0.7129	Intermediate Similarity	NPD6684	Approved
0.7129	Intermediate Similarity	NPD7146	Approved
0.7129	Intermediate Similarity	NPD6409	Approved
0.7129	Intermediate Similarity	NPD5330	Approved
0.7117	Intermediate Similarity	NPD6008	Approved
0.7115	Intermediate Similarity	NPD6079	Approved
0.7103	Intermediate Similarity	NPD4755	Approved
0.7087	Intermediate Similarity	NPD6101	Approved
0.7087	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7075	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD7736	Approved
0.7059	Intermediate Similarity	NPD6319	Approved
0.7049	Intermediate Similarity	NPD7507	Approved
0.7037	Intermediate Similarity	NPD5696	Approved
0.7009	Intermediate Similarity	NPD4697	Phase 3
0.7	Intermediate Similarity	NPD8033	Approved
0.6991	Remote Similarity	NPD6686	Approved
0.699	Remote Similarity	NPD6672	Approved
0.699	Remote Similarity	NPD5737	Approved
0.699	Remote Similarity	NPD6903	Approved
0.6972	Remote Similarity	NPD5286	Approved
0.6972	Remote Similarity	NPD4700	Approved
0.6972	Remote Similarity	NPD4696	Approved
0.6972	Remote Similarity	NPD5285	Approved
0.6949	Remote Similarity	NPD6009	Approved
0.6931	Remote Similarity	NPD3133	Approved
0.6931	Remote Similarity	NPD3665	Phase 1
0.6931	Remote Similarity	NPD3668	Phase 3
0.6931	Remote Similarity	NPD3666	Approved
0.6917	Remote Similarity	NPD8294	Approved
0.6917	Remote Similarity	NPD8377	Approved
0.6916	Remote Similarity	NPD5695	Phase 3
0.6909	Remote Similarity	NPD5223	Approved
0.6907	Remote Similarity	NPD6116	Phase 1
0.6903	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6891	Remote Similarity	NPD6335	Approved
0.6885	Remote Similarity	NPD7604	Phase 2
0.688	Remote Similarity	NPD7319	Approved
0.6864	Remote Similarity	NPD6274	Approved
0.686	Remote Similarity	NPD8379	Approved
0.686	Remote Similarity	NPD8296	Approved
0.686	Remote Similarity	NPD8517	Approved
0.686	Remote Similarity	NPD5983	Phase 2
0.686	Remote Similarity	NPD8516	Approved
0.686	Remote Similarity	NPD8515	Approved
0.686	Remote Similarity	NPD8378	Approved
0.686	Remote Similarity	NPD8380	Approved
0.686	Remote Similarity	NPD8513	Phase 3
0.686	Remote Similarity	NPD8335	Approved
0.6855	Remote Similarity	NPD8293	Discontinued
0.6852	Remote Similarity	NPD5221	Approved
0.6852	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6852	Remote Similarity	NPD5222	Approved
0.6847	Remote Similarity	NPD5225	Approved
0.6847	Remote Similarity	NPD4633	Approved
0.6847	Remote Similarity	NPD5226	Approved
0.6847	Remote Similarity	NPD5211	Phase 2
0.6847	Remote Similarity	NPD5224	Approved
0.6833	Remote Similarity	NPD7101	Approved
0.6833	Remote Similarity	NPD7100	Approved
0.6833	Remote Similarity	NPD7516	Approved
0.6829	Remote Similarity	NPD7492	Approved
0.6807	Remote Similarity	NPD6317	Approved
0.6804	Remote Similarity	NPD6117	Approved
0.6796	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6796	Remote Similarity	NPD6098	Approved
0.6792	Remote Similarity	NPD5284	Approved
0.6792	Remote Similarity	NPD5281	Approved
0.6789	Remote Similarity	NPD5173	Approved
0.6786	Remote Similarity	NPD5174	Approved
0.6786	Remote Similarity	NPD4754	Approved
0.6786	Remote Similarity	NPD5175	Approved
0.6777	Remote Similarity	NPD6059	Approved
0.6777	Remote Similarity	NPD6054	Approved
0.6774	Remote Similarity	NPD6616	Approved
0.6774	Remote Similarity	NPD6336	Discontinued
0.6762	Remote Similarity	NPD6080	Approved
0.6762	Remote Similarity	NPD6673	Approved
0.6762	Remote Similarity	NPD4753	Phase 2
0.6762	Remote Similarity	NPD6904	Approved
0.675	Remote Similarity	NPD6313	Approved
0.675	Remote Similarity	NPD6314	Approved
0.675	Remote Similarity	NPD7327	Approved
0.675	Remote Similarity	NPD7328	Approved
0.6729	Remote Similarity	NPD5779	Approved
0.6729	Remote Similarity	NPD5778	Approved
0.6726	Remote Similarity	NPD5141	Approved
0.6724	Remote Similarity	NPD4634	Approved
0.6723	Remote Similarity	NPD6868	Approved
0.6721	Remote Similarity	NPD6908	Approved
0.6721	Remote Similarity	NPD6909	Approved
0.6721	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.672	Remote Similarity	NPD7078	Approved
0.6701	Remote Similarity	NPD7339	Approved
0.6701	Remote Similarity	NPD6942	Approved
0.67	Remote Similarity	NPD4695	Discontinued
0.6697	Remote Similarity	NPD7732	Phase 3
0.6697	Remote Similarity	NPD7614	Phase 1
0.6696	Remote Similarity	NPD7632	Discontinued
0.6667	Remote Similarity	NPD6115	Approved
0.6667	Remote Similarity	NPD6697	Approved
0.6667	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6118	Approved
0.6667	Remote Similarity	NPD6114	Approved
0.6667	Remote Similarity	NPD4768	Approved
0.6667	Remote Similarity	NPD6001	Approved
0.6667	Remote Similarity	NPD4767	Approved
0.6667	Remote Similarity	NPD6370	Approved
0.6633	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6607	Remote Similarity	NPD5344	Discontinued
0.6606	Remote Similarity	NPD5210	Approved
0.6606	Remote Similarity	NPD4629	Approved
0.6598	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6585	Remote Similarity	NPD6015	Approved
0.6585	Remote Similarity	NPD7503	Approved
0.6585	Remote Similarity	NPD6016	Approved
0.6585	Remote Similarity	NPD6921	Approved
0.6571	Remote Similarity	NPD7524	Approved
0.6569	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6569	Remote Similarity	NPD4221	Approved
0.6569	Remote Similarity	NPD4223	Phase 3
0.6552	Remote Similarity	NPD4729	Approved
0.6552	Remote Similarity	NPD5128	Approved
0.6552	Remote Similarity	NPD4730	Approved
0.6542	Remote Similarity	NPD46	Approved
0.6542	Remote Similarity	NPD6698	Approved
0.6538	Remote Similarity	NPD1694	Approved
0.6538	Remote Similarity	NPD5329	Approved
0.6532	Remote Similarity	NPD5988	Approved
0.6509	Remote Similarity	NPD5208	Approved
0.6505	Remote Similarity	NPD4788	Approved
0.6481	Remote Similarity	NPD7983	Approved
0.6481	Remote Similarity	NPD6050	Approved
0.6481	Remote Similarity	NPD5693	Phase 1
0.648	Remote Similarity	NPD6067	Discontinued

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