NPASS Compound

Structure

NPC190849 OpenBabel07101719402D 44 49 0 0 1 0 0 0 0 0999 V2000 -4.4972 0.4566 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0210 -1.0866 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5261 1.4700 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0361 0.6213 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.9600 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8487 -1.4700 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.9800 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9409 -0.4900 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0922 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7896 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0922 0.9800 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7896 0.9800 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9409 2.4500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6974 0.9800 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8487 1.4700 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0922 2.9400 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6974 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8487 -0.4900 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2435 -1.4700 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8487 -1.4700 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3948 -1.9600 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6974 -1.9600 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3948 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8487 2.4500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9409 1.4700 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6974 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5461 -0.4900 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6974 2.9400 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6974 0.9800 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 0.9800 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.2435 2.4500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5461 2.4500 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5461 -2.4500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2435 -0.4900 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5461 1.4700 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8487 1.4700 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8487 -0.4900 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 -2.5461 -1.4700 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6974 3.9200 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2435 1.4700 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6974 -2.9400 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3948 -2.9400 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3948 2.9400 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 34 1 0 0 0 0 2 34 1 0 0 0 0 3 35 1 0 0 0 0 4 35 1 0 0 0 0 6 37 1 0 0 0 0 8 9 2 0 0 0 0 8 10 1 0 0 0 0 9 11 1 0 0 0 0 10 12 2 0 0 0 0 11 25 2 0 0 0 0 12 25 1 0 0 0 0 13 16 2 0 0 0 0 13 25 1 0 0 0 0 14 15 1 0 0 0 0 14 26 2 0 0 0 0 15 30 1 0 0 0 0 16 31 1 0 0 0 0 17 18 1 0 0 0 0 17 29 1 0 0 0 0 18 38 1 0 0 0 0 19 21 1 0 0 0 0 19 34 1 0 0 0 0 20 22 1 0 0 0 0 20 37 1 0 0 0 0 21 39 1 0 0 0 0 22 39 1 0 0 0 0 23 27 1 0 0 0 0 23 34 1 0 0 0 0 24 28 1 0 0 0 0 24 36 1 0 0 0 0 26 27 1 0 0 0 0 26 37 1 0 0 0 0 27 39 1 1 0 0 0 28 32 1 0 0 0 0 28 40 1 1 0 0 0 29 35 1 0 0 0 0 29 36 1 6 0 0 0 30 36 1 6 0 0 0 30 38 1 0 0 0 0 31 41 2 0 0 0 0 31 44 1 0 0 0 0 32 35 1 0 0 0 0 32 44 1 6 0 0 0 33 42 2 0 0 0 0 33 43 1 0 0 0 0 36 5 1 6 0 0 0 37 38 1 6 0 0 0 38 7 1 6 0 0 0 39 33 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	602.4
Volume:	657.257
LogP:	7.497
LogD:	5.358
LogS:	-5.687
# Rotatable Bonds:	5
TPSA:	83.83
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	6
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.205
Synthetic Accessibility Score:	4.87
Fsp3:	0.692
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:	-5.423
MDCK Permeability:	2.9167425964260474e-05
Pgp-inhibitor:	0.027
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.005
30% Bioavailability (F30%):	0.4

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.023
Plasma Protein Binding (PPB):	100.04452514648438%
Volume Distribution (VD):	0.867
Pgp-substrate:	3.4834022521972656%

ADMET: Metabolism

CYP1A2-inhibitor:	0.029
CYP1A2-substrate:	0.204
CYP2C19-inhibitor:	0.072
CYP2C19-substrate:	0.786
CYP2C9-inhibitor:	0.282
CYP2C9-substrate:	0.07
CYP2D6-inhibitor:	0.043
CYP2D6-substrate:	0.04
CYP3A4-inhibitor:	0.388
CYP3A4-substrate:	0.469

ADMET: Excretion

Clearance (CL):	2.368
Half-life (T1/2):	0.039

ADMET: Toxicity

hERG Blockers:	0.007
Human Hepatotoxicity (H-HT):	0.165
Drug-inuced Liver Injury (DILI):	0.023
AMES Toxicity:	0.003
Rat Oral Acute Toxicity:	0.1
Maximum Recommended Daily Dose:	0.892
Skin Sensitization:	0.08
Carcinogencity:	0.043
Eye Corrosion:	0.005
Eye Irritation:	0.044
Respiratory Toxicity:	0.965

Download Data

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

Natural Product: NPC190849

Natural Product ID:	NPC190849
*Common Name:**	3-Cis-P-Coumaroyl Maslinic Acid
IUPAC Name:	(4aS,6aR,6aS,6bR,8aR,10R,11R,12aR,14bS)-11-hydroxy-2,2,6a,6b,9,9,12a-heptamethyl-10-[(Z)-3-phenylprop-2-enoyl]oxy-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylic acid
Synonyms:
Standard InCHIKey:	QYNZDAXHBDWWFS-GZOAODGCSA-N
Standard InCHI:	InChI=1S/C39H54O5/c1-34(2)19-21-39(33(42)43)22-20-37(6)26(27(39)23-34)14-15-30-36(5)24-28(40)32(35(3,4)29(36)17-18-38(30,37)7)44-31(41)16-13-25-11-9-8-10-12-25/h8-14,16,27-30,32,40H,15,17-24H2,1-7H3,(H,42,43)/b16-13-/t27-,28+,29-,30+,32-,36-,37+,38+,39-/m0/s1
SMILES:	CC1(C)CC[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)OC(=O)/C=Cc3ccccc3)O)[C@@H]2C1)C(=O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL463995
PubChem CID:	16664518
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
NPO24979	Tetracera boiviniana	Species	Dilleniaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10654414]
NPO24979	Tetracera boiviniana	Species	Dilleniaceae	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	2
Others	4

Activity Type	# Activity
CELL-LINE	1
Individual Protein	4
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2216	Individual Protein	DNA polymerase beta	Rattus norvegicus	IC50	=	15000.0	nM	PMID[527367]
NPT2216	Individual Protein	DNA polymerase beta	Rattus norvegicus	IC50	=	7500.0	nM	PMID[527367]
NPT2216	Individual Protein	DNA polymerase beta	Rattus norvegicus	Inhibition	=	89.0	%	PMID[527367]
NPT2216	Individual Protein	DNA polymerase beta	Rattus norvegicus	Inhibition	=	70.0	%	PMID[527367]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	100.0	%	PMID[527367]
NPT26575	CELL-LINE	P388D1	Mus musculus	Activity	=	77.0	%	PMID[527367]

☑ 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 NPC190849 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	273
0.1-0.2	1007
0.2-0.3	2117
0.3-0.4	4975
0.4-0.5	9544
0.5-0.6	17612
0.6-0.7	6126
0.7-0.8	891
0.8-0.85	105
0.85-0.9	40
0.9-0.95	2
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC171007
0.9593	High Similarity	NPC475138
0.8947	High Similarity	NPC304110
0.8947	High Similarity	NPC27518
0.875	High Similarity	NPC25491
0.8741	High Similarity	NPC477468
0.8682	High Similarity	NPC473443
0.8676	High Similarity	NPC111466
0.8647	High Similarity	NPC249817
0.8613	High Similarity	NPC40085
0.8613	High Similarity	NPC264270
0.8605	High Similarity	NPC225103
0.8594	High Similarity	NPC470753
0.8594	High Similarity	NPC473220
0.8582	High Similarity	NPC216940
0.8582	High Similarity	NPC22676
0.8582	High Similarity	NPC198621
0.8582	High Similarity	NPC475482
0.8571	High Similarity	NPC477874
0.8571	High Similarity	NPC173569
0.855	High Similarity	NPC80599
0.854	High Similarity	NPC469447
0.854	High Similarity	NPC477873
0.8538	High Similarity	NPC472388
0.8529	High Similarity	NPC475513
0.8529	High Similarity	NPC473755
0.8516	High Similarity	NPC470765
0.8485	Intermediate Similarity	NPC472437
0.8473	Intermediate Similarity	NPC472361
0.8456	Intermediate Similarity	NPC224491
0.8429	Intermediate Similarity	NPC301556
0.8429	Intermediate Similarity	NPC471101
0.8429	Intermediate Similarity	NPC266265
0.8429	Intermediate Similarity	NPC270590
0.8429	Intermediate Similarity	NPC92293
0.8425	Intermediate Similarity	NPC12016
0.8421	Intermediate Similarity	NPC203486
0.8417	Intermediate Similarity	NPC53520
0.8409	Intermediate Similarity	NPC209851
0.8406	Intermediate Similarity	NPC475122
0.8372	Intermediate Similarity	NPC275576
0.8372	Intermediate Similarity	NPC475933
0.8372	Intermediate Similarity	NPC470158
0.8372	Intermediate Similarity	NPC473082
0.837	Intermediate Similarity	NPC39549
0.8359	Intermediate Similarity	NPC140118
0.8359	Intermediate Similarity	NPC12881
0.8359	Intermediate Similarity	NPC472373
0.8358	Intermediate Similarity	NPC477896
0.8357	Intermediate Similarity	NPC281717
0.8345	Intermediate Similarity	NPC476973
0.8345	Intermediate Similarity	NPC171525
0.8345	Intermediate Similarity	NPC29704
0.8345	Intermediate Similarity	NPC473088
0.8345	Intermediate Similarity	NPC472572
0.8345	Intermediate Similarity	NPC470159
0.8345	Intermediate Similarity	NPC70403
0.8345	Intermediate Similarity	NPC200471
0.8345	Intermediate Similarity	NPC471104
0.8345	Intermediate Similarity	NPC174982
0.8345	Intermediate Similarity	NPC470157
0.8345	Intermediate Similarity	NPC177940
0.8345	Intermediate Similarity	NPC472571
0.8345	Intermediate Similarity	NPC472556
0.8345	Intermediate Similarity	NPC96903
0.8345	Intermediate Similarity	NPC158663
0.8345	Intermediate Similarity	NPC184817
0.8345	Intermediate Similarity	NPC472568
0.8345	Intermediate Similarity	NPC469349
0.8345	Intermediate Similarity	NPC472575
0.8333	Intermediate Similarity	NPC91703
0.8322	Intermediate Similarity	NPC118033
0.831	Intermediate Similarity	NPC329657
0.8308	Intermediate Similarity	NPC169913
0.8308	Intermediate Similarity	NPC476972
0.8308	Intermediate Similarity	NPC476971
0.8296	Intermediate Similarity	NPC472372
0.8296	Intermediate Similarity	NPC472551
0.8296	Intermediate Similarity	NPC472545
0.8296	Intermediate Similarity	NPC472374
0.8295	Intermediate Similarity	NPC471758
0.8284	Intermediate Similarity	NPC126516
0.8284	Intermediate Similarity	NPC475627
0.8284	Intermediate Similarity	NPC475346
0.8284	Intermediate Similarity	NPC18982
0.8284	Intermediate Similarity	NPC48929
0.8284	Intermediate Similarity	NPC475457
0.8273	Intermediate Similarity	NPC11685
0.8273	Intermediate Similarity	NPC472569
0.8273	Intermediate Similarity	NPC95810
0.8273	Intermediate Similarity	NPC95265
0.8273	Intermediate Similarity	NPC163719
0.8273	Intermediate Similarity	NPC57628
0.8273	Intermediate Similarity	NPC472573
0.8273	Intermediate Similarity	NPC25768
0.8273	Intermediate Similarity	NPC70716
0.8273	Intermediate Similarity	NPC125106
0.8273	Intermediate Similarity	NPC241951
0.8273	Intermediate Similarity	NPC188865
0.8273	Intermediate Similarity	NPC476974
0.8273	Intermediate Similarity	NPC472570
0.8273	Intermediate Similarity	NPC475759
0.8273	Intermediate Similarity	NPC470152
0.8271	Intermediate Similarity	NPC476976
0.8264	Intermediate Similarity	NPC475579
0.8264	Intermediate Similarity	NPC473773
0.8261	Intermediate Similarity	NPC472801
0.8261	Intermediate Similarity	NPC34012
0.8261	Intermediate Similarity	NPC172311
0.8248	Intermediate Similarity	NPC472547
0.8248	Intermediate Similarity	NPC182249
0.8248	Intermediate Similarity	NPC100913
0.8248	Intermediate Similarity	NPC234548
0.8248	Intermediate Similarity	NPC248287
0.8248	Intermediate Similarity	NPC275592
0.8244	Intermediate Similarity	NPC195224
0.824	Intermediate Similarity	NPC152812
0.8231	Intermediate Similarity	NPC45821
0.8231	Intermediate Similarity	NPC476970
0.8227	Intermediate Similarity	NPC8102
0.8227	Intermediate Similarity	NPC66894
0.8222	Intermediate Similarity	NPC477893
0.8217	Intermediate Similarity	NPC469742
0.8203	Intermediate Similarity	NPC473749
0.8201	Intermediate Similarity	NPC163087
0.8195	Intermediate Similarity	NPC472418
0.8195	Intermediate Similarity	NPC476977
0.8194	Intermediate Similarity	NPC304876
0.8194	Intermediate Similarity	NPC249471
0.8194	Intermediate Similarity	NPC1173
0.8194	Intermediate Similarity	NPC257213
0.8194	Intermediate Similarity	NPC472022
0.8194	Intermediate Similarity	NPC472030
0.8194	Intermediate Similarity	NPC265395
0.8194	Intermediate Similarity	NPC69425
0.8194	Intermediate Similarity	NPC473680
0.8194	Intermediate Similarity	NPC475311
0.8194	Intermediate Similarity	NPC472005
0.8194	Intermediate Similarity	NPC158333
0.8194	Intermediate Similarity	NPC242262
0.8194	Intermediate Similarity	NPC473414
0.8194	Intermediate Similarity	NPC237549
0.8194	Intermediate Similarity	NPC256142
0.8194	Intermediate Similarity	NPC473579
0.8194	Intermediate Similarity	NPC475454
0.8189	Intermediate Similarity	NPC472679
0.8189	Intermediate Similarity	NPC472680
0.8188	Intermediate Similarity	NPC41481
0.8188	Intermediate Similarity	NPC97947
0.8188	Intermediate Similarity	NPC155192
0.8188	Intermediate Similarity	NPC271494
0.8188	Intermediate Similarity	NPC473591
0.8188	Intermediate Similarity	NPC291599
0.8188	Intermediate Similarity	NPC16912
0.8188	Intermediate Similarity	NPC472576
0.8188	Intermediate Similarity	NPC470616
0.8188	Intermediate Similarity	NPC118080
0.8188	Intermediate Similarity	NPC470617
0.8188	Intermediate Similarity	NPC27377
0.8188	Intermediate Similarity	NPC87448
0.8175	Intermediate Similarity	NPC89324
0.8169	Intermediate Similarity	NPC473215
0.8169	Intermediate Similarity	NPC476975
0.8168	Intermediate Similarity	NPC473423
0.816	Intermediate Similarity	NPC470820
0.8156	Intermediate Similarity	NPC474935
0.8156	Intermediate Similarity	NPC473602
0.8154	Intermediate Similarity	NPC114927
0.8154	Intermediate Similarity	NPC473083
0.8148	Intermediate Similarity	NPC329913
0.814	Intermediate Similarity	NPC473870
0.814	Intermediate Similarity	NPC473871
0.8138	Intermediate Similarity	NPC228204
0.8138	Intermediate Similarity	NPC26033
0.8138	Intermediate Similarity	NPC112523
0.8138	Intermediate Similarity	NPC114410
0.8134	Intermediate Similarity	NPC475493
0.8129	Intermediate Similarity	NPC472546
0.8125	Intermediate Similarity	NPC477905
0.8125	Intermediate Similarity	NPC472548
0.8125	Intermediate Similarity	NPC327962
0.812	Intermediate Similarity	NPC86257
0.8116	Intermediate Similarity	NPC97667
0.8116	Intermediate Similarity	NPC90614
0.8116	Intermediate Similarity	NPC171207
0.8116	Intermediate Similarity	NPC139243
0.8116	Intermediate Similarity	NPC116742
0.8116	Intermediate Similarity	NPC473440
0.8112	Intermediate Similarity	NPC7095
0.8112	Intermediate Similarity	NPC473214
0.8112	Intermediate Similarity	NPC470245
0.8092	Intermediate Similarity	NPC473111
0.8092	Intermediate Similarity	NPC473110
0.8088	Intermediate Similarity	NPC471864
0.8085	Intermediate Similarity	NPC277053
0.8085	Intermediate Similarity	NPC301946
0.8071	Intermediate Similarity	NPC147217
0.8071	Intermediate Similarity	NPC475429
0.8071	Intermediate Similarity	NPC191082
0.8071	Intermediate Similarity	NPC139067

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 NPC190849 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	232
0.1-0.2	739
0.2-0.3	1443
0.3-0.4	2991
0.4-0.5	2269
0.5-0.6	1284
0.6-0.7	177
0.7-0.8	14
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
0.8333	Intermediate Similarity	NPD8166	Discontinued
0.784	Intermediate Similarity	NPD7094	Approved
0.784	Intermediate Similarity	NPD6858	Approved
0.7717	Intermediate Similarity	NPD2629	Approved
0.7708	Intermediate Similarity	NPD7236	Approved
0.7609	Intermediate Similarity	NPD7961	Discontinued
0.7591	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7519	Intermediate Similarity	NPD4198	Discontinued
0.7464	Intermediate Similarity	NPD7008	Discontinued
0.745	Intermediate Similarity	NPD7239	Suspended
0.7402	Intermediate Similarity	NPD4141	Clinical (unspecified phase)
0.7398	Intermediate Similarity	NPD6647	Phase 2
0.7372	Intermediate Similarity	NPD8127	Discontinued
0.7364	Intermediate Similarity	NPD6010	Discontinued
0.7339	Intermediate Similarity	NPD5909	Discontinued
0.7295	Intermediate Similarity	NPD7798	Approved
0.7285	Intermediate Similarity	NPD7458	Discontinued
0.7273	Intermediate Similarity	NPD7610	Discontinued
0.7231	Intermediate Similarity	NPD4869	Clinical (unspecified phase)
0.7211	Intermediate Similarity	NPD7003	Approved
0.72	Intermediate Similarity	NPD6273	Approved
0.7185	Intermediate Similarity	NPD7457	Clinical (unspecified phase)
0.7183	Intermediate Similarity	NPD7966	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD5951	Approved
0.7167	Intermediate Similarity	NPD7748	Approved
0.7167	Intermediate Similarity	NPD5122	Clinical (unspecified phase)
0.7113	Intermediate Similarity	NPD6663	Approved
0.7111	Intermediate Similarity	NPD7163	Clinical (unspecified phase)
0.7109	Intermediate Similarity	NPD6831	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD8470	Clinical (unspecified phase)
0.7071	Intermediate Similarity	NPD5736	Approved
0.7037	Intermediate Similarity	NPD7799	Discontinued
0.7016	Intermediate Similarity	NPD2066	Phase 3
0.7007	Intermediate Similarity	NPD7702	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD7057	Phase 3
0.7006	Intermediate Similarity	NPD7058	Phase 2
0.7	Intermediate Similarity	NPD7515	Phase 2
0.6992	Remote Similarity	NPD7902	Approved
0.698	Remote Similarity	NPD4628	Phase 3
0.6923	Remote Similarity	NPD2067	Discontinued
0.6897	Remote Similarity	NPD6355	Discontinued
0.6875	Remote Similarity	NPD7714	Approved
0.6875	Remote Similarity	NPD7715	Approved
0.687	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD8368	Discontinued
0.6866	Remote Similarity	NPD7115	Discovery
0.6864	Remote Similarity	NPD8424	Clinical (unspecified phase)
0.6861	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.685	Remote Similarity	NPD1930	Approved
0.685	Remote Similarity	NPD1929	Approved
0.685	Remote Similarity	NPD1931	Clinical (unspecified phase)
0.6838	Remote Similarity	NPD7741	Discontinued
0.6822	Remote Similarity	NPD6685	Approved
0.6821	Remote Similarity	NPD7274	Clinical (unspecified phase)
0.6806	Remote Similarity	NPD6798	Discontinued
0.6803	Remote Similarity	NPD7097	Phase 1
0.6784	Remote Similarity	NPD8360	Approved
0.6784	Remote Similarity	NPD8361	Approved
0.6784	Remote Similarity	NPD8435	Approved
0.6783	Remote Similarity	NPD7055	Discontinued
0.6759	Remote Similarity	NPD8032	Phase 2
0.6755	Remote Similarity	NPD4110	Phase 3
0.6755	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6748	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6748	Remote Similarity	NPD7900	Approved
0.6746	Remote Similarity	NPD8407	Phase 2
0.6744	Remote Similarity	NPD5048	Discontinued
0.6743	Remote Similarity	NPD8485	Approved
0.6736	Remote Similarity	NPD7095	Approved
0.6731	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6718	Remote Similarity	NPD2182	Approved
0.6715	Remote Similarity	NPD7009	Phase 2
0.6714	Remote Similarity	NPD6637	Approved
0.6713	Remote Similarity	NPD7084	Phase 3
0.6712	Remote Similarity	NPD4140	Approved
0.6686	Remote Similarity	NPD8312	Approved
0.6686	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6686	Remote Similarity	NPD8313	Approved
0.6667	Remote Similarity	NPD8455	Phase 2
0.6667	Remote Similarity	NPD8434	Phase 2
0.6667	Remote Similarity	NPD8150	Discontinued
0.6667	Remote Similarity	NPD7638	Approved
0.6667	Remote Similarity	NPD690	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD1088	Approved
0.6646	Remote Similarity	NPD6677	Suspended
0.6645	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6644	Remote Similarity	NPD7305	Phase 1
0.6643	Remote Similarity	NPD4807	Approved
0.6643	Remote Similarity	NPD4806	Approved
0.6643	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6643	Remote Similarity	NPD6287	Discontinued
0.6641	Remote Similarity	NPD1932	Approved
0.664	Remote Similarity	NPD1989	Approved
0.6639	Remote Similarity	NPD3672	Approved
0.6639	Remote Similarity	NPD3673	Approved
0.6629	Remote Similarity	NPD8486	Clinical (unspecified phase)
0.6619	Remote Similarity	NPD3019	Approved
0.6619	Remote Similarity	NPD5125	Phase 3
0.6619	Remote Similarity	NPD2932	Approved
0.6619	Remote Similarity	NPD5305	Approved
0.6619	Remote Similarity	NPD5306	Approved
0.6619	Remote Similarity	NPD5126	Approved
0.6614	Remote Similarity	NPD7640	Approved
0.6614	Remote Similarity	NPD7639	Approved
0.6601	Remote Similarity	NPD6190	Approved
0.6591	Remote Similarity	NPD2329	Discontinued
0.6589	Remote Similarity	NPD5738	Clinical (unspecified phase)
0.6589	Remote Similarity	NPD5765	Approved
0.6587	Remote Similarity	NPD3495	Discontinued
0.6582	Remote Similarity	NPD7028	Phase 2
0.6581	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.656	Remote Similarity	NPD6048	Clinical (unspecified phase)
0.656	Remote Similarity	NPD6049	Phase 2
0.6557	Remote Similarity	NPD5346	Phase 2
0.6557	Remote Similarity	NPD5347	Phase 2
0.6556	Remote Similarity	NPD5763	Approved
0.6556	Remote Similarity	NPD5762	Approved
0.6556	Remote Similarity	NPD7266	Discontinued
0.6535	Remote Similarity	NPD9495	Approved
0.6535	Remote Similarity	NPD5926	Approved
0.6535	Remote Similarity	NPD4225	Approved
0.6531	Remote Similarity	NPD7713	Phase 3
0.6531	Remote Similarity	NPD6233	Phase 2
0.6528	Remote Similarity	NPD6085	Phase 2
0.6528	Remote Similarity	NPD5740	Clinical (unspecified phase)
0.6527	Remote Similarity	NPD7228	Approved
0.6512	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6504	Remote Similarity	NPD1089	Approved
0.6504	Remote Similarity	NPD1086	Approved
0.6504	Remote Similarity	NPD1090	Approved
0.6503	Remote Similarity	NPD1283	Approved
0.65	Remote Similarity	NPD37	Approved
0.6496	Remote Similarity	NPD3317	Approved
0.649	Remote Similarity	NPD5408	Approved
0.649	Remote Similarity	NPD5404	Approved
0.649	Remote Similarity	NPD5405	Approved
0.649	Remote Similarity	NPD2438	Suspended
0.649	Remote Similarity	NPD5406	Approved
0.6488	Remote Similarity	NPD5844	Phase 1
0.6486	Remote Similarity	NPD4060	Phase 1
0.6484	Remote Similarity	NPD1238	Approved
0.6481	Remote Similarity	NPD4967	Phase 2
0.6481	Remote Similarity	NPD4966	Approved
0.6481	Remote Similarity	NPD4965	Approved
0.6474	Remote Similarity	NPD7446	Clinical (unspecified phase)
0.6466	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6463	Remote Similarity	NPD3764	Approved
0.6458	Remote Similarity	NPD2797	Approved
0.6454	Remote Similarity	NPD4135	Approved
0.6454	Remote Similarity	NPD3026	Approved
0.6454	Remote Similarity	NPD3023	Approved
0.6454	Remote Similarity	NPD4106	Approved
0.6454	Remote Similarity	NPD4136	Approved
0.6447	Remote Similarity	NPD2346	Discontinued
0.6444	Remote Similarity	NPD8297	Approved
0.6444	Remote Similarity	NPD6912	Phase 3
0.6443	Remote Similarity	NPD5735	Approved
0.6433	Remote Similarity	NPD8658	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD3025	Approved
0.6429	Remote Similarity	NPD688	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD3024	Approved
0.6429	Remote Similarity	NPD1693	Approved
0.6424	Remote Similarity	NPD2799	Discontinued
0.6423	Remote Similarity	NPD800	Approved
0.642	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6412	Remote Similarity	NPD1237	Approved
0.6412	Remote Similarity	NPD164	Approved
0.6408	Remote Similarity	NPD3092	Approved
0.6405	Remote Similarity	NPD4534	Discontinued
0.6403	Remote Similarity	NPD6065	Approved
0.6402	Remote Similarity	NPD6234	Discontinued
0.64	Remote Similarity	NPD7631	Approved
0.6393	Remote Similarity	NPD4793	Discontinued
0.6391	Remote Similarity	NPD6686	Approved
0.6383	Remote Similarity	NPD3095	Discontinued
0.6383	Remote Similarity	NPD4199	Phase 3
0.638	Remote Similarity	NPD7768	Phase 2
0.6376	Remote Similarity	NPD3620	Phase 2
0.6376	Remote Similarity	NPD5121	Approved
0.6376	Remote Similarity	NPD2979	Phase 3
0.6376	Remote Similarity	NPD5120	Approved
0.6376	Remote Similarity	NPD5119	Approved
0.6376	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6374	Remote Similarity	NPD7240	Approved
0.6369	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD5734	Clinical (unspecified phase)
0.6358	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6358	Remote Similarity	NPD7819	Suspended
0.6357	Remote Similarity	NPD3091	Approved
0.6351	Remote Similarity	NPD3268	Approved
0.6345	Remote Similarity	NPD3094	Phase 2
0.6338	Remote Similarity	NPD8328	Phase 3
0.6328	Remote Similarity	NPD1564	Approved
0.6328	Remote Similarity	NPD1565	Approved
0.6328	Remote Similarity	NPD1566	Phase 3
0.6327	Remote Similarity	NPD4620	Approved
0.6327	Remote Similarity	NPD5203	Approved
0.6327	Remote Similarity	NPD4617	Approved
0.6327	Remote Similarity	NPD5201	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