NPASS Compound

Structure

CID274268 OpenBabel06191716082D 51 55 0 0 1 0 0 0 0 0999 V2000 0.2733 4.5647 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.1154 2.9270 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.4383 0.5934 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9633 -2.7888 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2090 1.1255 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2102 0.8073 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9173 2.0940 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6002 0.9228 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7339 0.6882 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0088 2.2389 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5112 3.0853 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2046 1.2768 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1467 4.0865 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0701 3.8583 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9357 3.2925 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6987 0.5763 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0573 -1.2664 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2342 3.7242 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.1077 1.9452 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -9.5919 1.0910 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -1.9169 -1.8081 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.0554 0.6280 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.1275 4.1329 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8725 3.2925 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4731 2.6186 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9419 -1.6924 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.0775 0.3032 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.3472 -0.3404 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.7335 1.5575 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.6101 1.0988 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -3.3351 2.6186 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8766 -1.6010 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.7560 0.6146 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0477 -0.3538 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8502 -0.1419 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7171 -1.0934 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.6410 -0.5763 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.7611 1.7340 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0 -4.4478 2.4969 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -6.9096 1.1122 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -5.7070 1.6847 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.7482 -0.3672 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.8941 -0.8514 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.4160 0.6605 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3899 -1.2112 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.0471 1.7340 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.0168 0.0175 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2694 -0.8951 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1936 -0.8380 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.7364 -2.0750 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 20 1 0 0 0 0 7 41 1 0 0 0 0 8 47 1 0 0 0 0 9 48 1 0 0 0 0 10 11 1 0 0 0 0 10 12 2 0 0 0 0 11 18 2 0 0 0 0 12 27 1 0 0 0 0 13 18 1 0 0 0 0 13 23 1 0 0 0 0 14 23 2 0 0 0 0 14 24 1 0 0 0 0 15 23 1 0 0 0 0 15 25 2 0 0 0 0 16 28 1 0 0 0 0 16 29 1 0 0 0 0 17 37 1 0 0 0 0 19 20 1 0 0 0 0 19 30 1 0 0 0 0 20 30 1 0 0 0 0 21 4 1 1 0 0 0 21 26 1 0 0 0 0 21 32 1 0 0 0 0 22 5 1 1 0 0 0 22 34 1 0 0 0 0 22 41 1 0 0 0 0 24 31 2 0 0 0 0 24 39 1 0 0 0 0 25 31 1 0 0 0 0 25 47 1 0 0 0 0 26 17 1 1 0 0 0 26 49 1 0 0 0 0 27 37 1 1 0 0 0 27 48 1 0 0 0 0 28 36 1 1 0 0 0 28 50 1 0 0 0 0 29 39 2 3 0 0 0 29 42 1 0 0 0 0 30 33 1 0 0 0 0 31 38 1 0 0 0 0 32 36 1 6 0 0 0 32 51 1 0 0 0 0 33 41 1 0 0 0 0 33 43 2 0 0 0 0 34 44 2 0 0 0 0 34 50 1 0 0 0 0 35 40 2 0 0 0 0 35 45 1 0 0 0 0 35 49 1 0 0 0 0 36 6 1 6 0 0 0 36 51 1 0 0 0 0 37 40 1 0 0 0 0 37 46 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	731.32
Volume:	718.101
LogP:	3.843
LogD:	2.847
LogS:	-4.578
# Rotatable Bonds:	8
TPSA:	165.26
# H-Bond Aceptor:	13
# H-Bond Donor:	3
# Rings:	5
# Heavy Atoms:	14

MedChem Properties

QED Drug-Likeness Score:	0.282
Synthetic Accessibility Score:	7.128
Fsp3:	0.622
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:	-5.234
MDCK Permeability:	2.0815668904106133e-05
Pgp-inhibitor:	0.999
Pgp-substrate:	0.995
Human Intestinal Absorption (HIA):	0.01
20% Bioavailability (F20%):	0.007
30% Bioavailability (F30%):	0.947

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.174
Plasma Protein Binding (PPB):	94.91565704345703%
Volume Distribution (VD):	0.594
Pgp-substrate:	5.944525718688965%

ADMET: Metabolism

CYP1A2-inhibitor:	0.005
CYP1A2-substrate:	0.127
CYP2C19-inhibitor:	0.039
CYP2C19-substrate:	0.789
CYP2C9-inhibitor:	0.049
CYP2C9-substrate:	0.029
CYP2D6-inhibitor:	0.007
CYP2D6-substrate:	0.181
CYP3A4-inhibitor:	0.824
CYP3A4-substrate:	0.918

ADMET: Excretion

Clearance (CL):	10.169
Half-life (T1/2):	0.165

ADMET: Toxicity

hERG Blockers:	0.053
Human Hepatotoxicity (H-HT):	0.765
Drug-inuced Liver Injury (DILI):	0.974
AMES Toxicity:	0.01
Rat Oral Acute Toxicity:	0.637
Maximum Recommended Daily Dose:	0.678
Skin Sensitization:	0.187
Carcinogencity:	0.036
Eye Corrosion:	0.003
Eye Irritation:	0.005
Respiratory Toxicity:	0.539

Download Data

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

Natural Product: NPC274268

Natural Product ID:	NPC274268
*Common Name:**	Normaytancyprine
IUPAC Name:	n.a.
Synonyms:	Normaytancyprine
Standard InCHIKey:	QUJBQBQAIZQWIV-UZTPMTCISA-N
Standard InCHI:	InChI=1S/C37H50ClN3O10/c1-18-11-10-12-27(48-9)37(46)17-26(49-35(45)40-37)21(4)32-36(6,51-32)28(50-34(44)22(5)41(7)33(43)30-19(2)20(30)3)16-29(42)39-24-14-23(13-18)15-25(47-8)31(24)38/h10-12,14-15,19-22,26-28,30,32,46H,13,16-17H2,1-9H3,(H,39,42)(H,40,45)/b12-10+,18-11+/t19?,20?,21-,22+,26+,27-,28+,30?,32+,36+,37+/m1/s1
SMILES:	C/C/1=CC=C[C@H]([C@]2(C[C@@H]([C@@H](C)[C@H]3[C@](C)([C@H](CC(=Nc4cc(C1)cc(c4Cl)OC)O)OC(=O)[C@H](C)N(C)C(=O)C1C(C)C1C)O3)OC(=N2)O)O)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL447165
PubChem CID:	44559322
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000064] Macrolactams

*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
NPO25424	Putterlickia verrucosa	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25424	Putterlickia verrucosa	Species	Celastraceae	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	1
Others	1

Activity Type	# Activity
Cell Line	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT168	Cell Line	P388	Mus musculus	T/C	=	145.0	%	PMID[569039]
NPT91	Cell Line	KB	Homo sapiens	ED50	=	0.000001	ug ml-1	PMID[569039]

☑ 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 NPC274268 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	323
0.1-0.2	1850
0.2-0.3	9276
0.3-0.4	9604
0.4-0.5	17391
0.5-0.6	3962
0.6-0.7	287
0.7-0.8	1
0.8-0.85	0
0.85-0.9	1
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.7156	Intermediate Similarity	NPC311357
0.7091	Intermediate Similarity	NPC473422
0.7067	Intermediate Similarity	NPC45112
0.7067	Intermediate Similarity	NPC271958
0.7067	Intermediate Similarity	NPC134413
0.7067	Intermediate Similarity	NPC263507
0.6934	Remote Similarity	NPC315542
0.6919	Remote Similarity	NPC86678
0.6916	Remote Similarity	NPC326027
0.6903	Remote Similarity	NPC471532
0.6903	Remote Similarity	NPC326333
0.6892	Remote Similarity	NPC473460
0.6875	Remote Similarity	NPC219350
0.6875	Remote Similarity	NPC194699
0.6802	Remote Similarity	NPC472330
0.6802	Remote Similarity	NPC472329
0.6794	Remote Similarity	NPC227778
0.6783	Remote Similarity	NPC471531
0.6754	Remote Similarity	NPC277306
0.6754	Remote Similarity	NPC469442
0.6752	Remote Similarity	NPC148124
0.6742	Remote Similarity	NPC323662
0.674	Remote Similarity	NPC471561
0.6739	Remote Similarity	NPC316297
0.6739	Remote Similarity	NPC66191
0.6739	Remote Similarity	NPC314817
0.6731	Remote Similarity	NPC151030
0.6731	Remote Similarity	NPC269383
0.6727	Remote Similarity	NPC149962
0.6727	Remote Similarity	NPC473371
0.6712	Remote Similarity	NPC123859
0.6709	Remote Similarity	NPC248903
0.6709	Remote Similarity	NPC99724
0.6705	Remote Similarity	NPC323858
0.6697	Remote Similarity	NPC144314
0.6696	Remote Similarity	NPC25539
0.6694	Remote Similarity	NPC213529
0.6683	Remote Similarity	NPC186617
0.6667	Remote Similarity	NPC50548
0.6667	Remote Similarity	NPC26928
0.6667	Remote Similarity	NPC225381
0.6654	Remote Similarity	NPC329480
0.6651	Remote Similarity	NPC471568
0.6651	Remote Similarity	NPC196091
0.6651	Remote Similarity	NPC473693
0.6636	Remote Similarity	NPC469830
0.6636	Remote Similarity	NPC328763
0.6621	Remote Similarity	NPC28510
0.6618	Remote Similarity	NPC472923
0.6607	Remote Similarity	NPC242728
0.6588	Remote Similarity	NPC248670
0.6588	Remote Similarity	NPC49315
0.6576	Remote Similarity	NPC313627
0.654	Remote Similarity	NPC310894
0.6537	Remote Similarity	NPC207675
0.6537	Remote Similarity	NPC212699
0.6514	Remote Similarity	NPC262725
0.6514	Remote Similarity	NPC291759
0.6507	Remote Similarity	NPC254700
0.6504	Remote Similarity	NPC49583
0.65	Remote Similarity	NPC174629
0.6476	Remote Similarity	NPC473502
0.6471	Remote Similarity	NPC473407
0.6471	Remote Similarity	NPC473378
0.6468	Remote Similarity	NPC133591
0.6465	Remote Similarity	NPC475421
0.646	Remote Similarity	NPC469443
0.6449	Remote Similarity	NPC168153
0.6443	Remote Similarity	NPC319774
0.6441	Remote Similarity	NPC204970
0.6438	Remote Similarity	NPC127996
0.6429	Remote Similarity	NPC314743
0.6425	Remote Similarity	NPC29531
0.6423	Remote Similarity	NPC3921
0.6419	Remote Similarity	NPC14339
0.6404	Remote Similarity	NPC474077
0.6402	Remote Similarity	NPC71539
0.6402	Remote Similarity	NPC471165
0.6402	Remote Similarity	NPC476227
0.6402	Remote Similarity	NPC250960
0.6402	Remote Similarity	NPC164608
0.6398	Remote Similarity	NPC238430
0.6396	Remote Similarity	NPC477526
0.6391	Remote Similarity	NPC172355
0.639	Remote Similarity	NPC266994
0.638	Remote Similarity	NPC295287
0.6379	Remote Similarity	NPC477160
0.6377	Remote Similarity	NPC10730
0.6377	Remote Similarity	NPC10875
0.6376	Remote Similarity	NPC470903
0.6376	Remote Similarity	NPC470112
0.6376	Remote Similarity	NPC167763
0.6364	Remote Similarity	NPC38823
0.6364	Remote Similarity	NPC276120
0.6364	Remote Similarity	NPC207033
0.636	Remote Similarity	NPC214368
0.6359	Remote Similarity	NPC39822
0.6359	Remote Similarity	NPC32064
0.6351	Remote Similarity	NPC64140
0.6351	Remote Similarity	NPC174122
0.6339	Remote Similarity	NPC314083
0.6337	Remote Similarity	NPC74216
0.6333	Remote Similarity	NPC72291
0.6327	Remote Similarity	NPC472191
0.6326	Remote Similarity	NPC474953
0.6326	Remote Similarity	NPC26108
0.6326	Remote Similarity	NPC473354
0.6325	Remote Similarity	NPC92235
0.6321	Remote Similarity	NPC314861
0.6318	Remote Similarity	NPC299806
0.6313	Remote Similarity	NPC287152
0.6311	Remote Similarity	NPC471563
0.6311	Remote Similarity	NPC477397
0.6311	Remote Similarity	NPC184933
0.6311	Remote Similarity	NPC59827
0.6306	Remote Similarity	NPC234069
0.6301	Remote Similarity	NPC469831
0.6301	Remote Similarity	NPC323198
0.63	Remote Similarity	NPC477552
0.63	Remote Similarity	NPC477550
0.6296	Remote Similarity	NPC50016
0.6296	Remote Similarity	NPC473458
0.6293	Remote Similarity	NPC220060
0.6279	Remote Similarity	NPC273755
0.6276	Remote Similarity	NPC108826
0.6273	Remote Similarity	NPC471050
0.6273	Remote Similarity	NPC471048
0.6273	Remote Similarity	NPC294951
0.6273	Remote Similarity	NPC469829
0.6273	Remote Similarity	NPC471049
0.627	Remote Similarity	NPC477393
0.6267	Remote Similarity	NPC203972
0.6266	Remote Similarity	NPC469444
0.6262	Remote Similarity	NPC40234
0.6256	Remote Similarity	NPC191863
0.6256	Remote Similarity	NPC133470
0.6256	Remote Similarity	NPC289776
0.625	Remote Similarity	NPC279871
0.625	Remote Similarity	NPC95412
0.625	Remote Similarity	NPC128115
0.6245	Remote Similarity	NPC477551
0.6245	Remote Similarity	NPC476661
0.6244	Remote Similarity	NPC294516
0.6244	Remote Similarity	NPC138083
0.6244	Remote Similarity	NPC474650
0.6244	Remote Similarity	NPC107938
0.6239	Remote Similarity	NPC269750
0.6239	Remote Similarity	NPC194671
0.6238	Remote Similarity	NPC301163
0.6233	Remote Similarity	NPC83241
0.623	Remote Similarity	NPC471513
0.6228	Remote Similarity	NPC477527
0.6227	Remote Similarity	NPC272375
0.6227	Remote Similarity	NPC475794
0.6223	Remote Similarity	NPC257266
0.6221	Remote Similarity	NPC477115
0.622	Remote Similarity	NPC477396
0.6217	Remote Similarity	NPC476662
0.6209	Remote Similarity	NPC320064
0.6208	Remote Similarity	NPC222046
0.6201	Remote Similarity	NPC267414
0.6199	Remote Similarity	NPC474607
0.6197	Remote Similarity	NPC257728
0.6195	Remote Similarity	NPC132771
0.619	Remote Similarity	NPC319320
0.619	Remote Similarity	NPC477395
0.619	Remote Similarity	NPC287757
0.6188	Remote Similarity	NPC232872
0.6186	Remote Similarity	NPC46009
0.6186	Remote Similarity	NPC475204
0.6186	Remote Similarity	NPC469445
0.6186	Remote Similarity	NPC475123
0.6185	Remote Similarity	NPC291173
0.6182	Remote Similarity	NPC476321
0.6179	Remote Similarity	NPC470821
0.6178	Remote Similarity	NPC248822
0.6176	Remote Similarity	NPC189661
0.6175	Remote Similarity	NPC158277
0.6175	Remote Similarity	NPC473402
0.6174	Remote Similarity	NPC127178
0.6171	Remote Similarity	NPC473007
0.617	Remote Similarity	NPC153365
0.617	Remote Similarity	NPC168250
0.6168	Remote Similarity	NPC19555
0.6168	Remote Similarity	NPC209463
0.6167	Remote Similarity	NPC77777
0.6165	Remote Similarity	NPC324081
0.6164	Remote Similarity	NPC126515
0.6164	Remote Similarity	NPC274002
0.6164	Remote Similarity	NPC45037
0.6164	Remote Similarity	NPC472331
0.6161	Remote Similarity	NPC230098
0.6157	Remote Similarity	NPC89831
0.6157	Remote Similarity	NPC230611
0.6154	Remote Similarity	NPC184161
0.6154	Remote Similarity	NPC471526
0.6148	Remote Similarity	NPC19175
0.6143	Remote Similarity	NPC56635
0.6141	Remote Similarity	NPC288110
0.6141	Remote Similarity	NPC37957

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 NPC274268 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	191
0.1-0.2	618
0.2-0.3	1128
0.3-0.4	2101
0.4-0.5	3342
0.5-0.6	1672
0.6-0.7	98
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7067	Intermediate Similarity	NPD7959	Clinical (unspecified phase)
0.7033	Intermediate Similarity	NPD8014	Clinical (unspecified phase)
0.6926	Remote Similarity	NPD7805	Phase 3
0.6906	Remote Similarity	NPD6905	Phase 2
0.6779	Remote Similarity	NPD2215	Approved
0.6779	Remote Similarity	NPD2216	Approved
0.6682	Remote Similarity	NPD2166	Phase 3
0.6667	Remote Similarity	NPD3437	Discontinued
0.6636	Remote Similarity	NPD5984	Phase 2
0.6622	Remote Similarity	NPD6034	Phase 2
0.6622	Remote Similarity	NPD4604	Approved
0.6622	Remote Similarity	NPD4605	Approved
0.659	Remote Similarity	NPD5565	Discontinued
0.6582	Remote Similarity	NPD3912	Discontinued
0.6547	Remote Similarity	NPD5650	Approved
0.6547	Remote Similarity	NPD5652	Approved
0.6547	Remote Similarity	NPD5651	Approved
0.6532	Remote Similarity	NPD4771	Phase 2
0.6507	Remote Similarity	NPD7263	Phase 2
0.6489	Remote Similarity	NPD7565	Approved
0.6457	Remote Similarity	NPD4523	Approved
0.6457	Remote Similarity	NPD7256	Discontinued
0.6452	Remote Similarity	NPD1381	Clinical (unspecified phase)
0.6432	Remote Similarity	NPD3416	Discontinued
0.6429	Remote Similarity	NPD5582	Discontinued
0.6425	Remote Similarity	NPD2843	Phase 2
0.6425	Remote Similarity	NPD7630	Phase 3
0.6425	Remote Similarity	NPD7629	Clinical (unspecified phase)
0.6425	Remote Similarity	NPD7628	Phase 3
0.6425	Remote Similarity	NPD2845	Phase 2
0.642	Remote Similarity	NPD7284	Clinical (unspecified phase)
0.6417	Remote Similarity	NPD8463	Approved
0.6416	Remote Similarity	NPD6874	Approved
0.6413	Remote Similarity	NPD7125	Discontinued
0.6409	Remote Similarity	NPD3065	Discontinued
0.6407	Remote Similarity	NPD8027	Approved
0.64	Remote Similarity	NPD2941	Discontinued
0.6398	Remote Similarity	NPD7129	Suspended
0.6396	Remote Similarity	NPD5871	Discontinued
0.6396	Remote Similarity	NPD6058	Phase 2
0.6381	Remote Similarity	NPD7975	Clinical (unspecified phase)
0.6376	Remote Similarity	NPD4012	Approved
0.6375	Remote Similarity	NPD7542	Phase 3
0.6368	Remote Similarity	NPD7485	Phase 3
0.6368	Remote Similarity	NPD5587	Approved
0.6368	Remote Similarity	NPD7484	Phase 3
0.636	Remote Similarity	NPD7476	Discontinued
0.6359	Remote Similarity	NPD2168	Clinical (unspecified phase)
0.6359	Remote Similarity	NPD2167	Clinical (unspecified phase)
0.6356	Remote Similarity	NPD8249	Clinical (unspecified phase)
0.6348	Remote Similarity	NPD7891	Discontinued
0.6335	Remote Similarity	NPD8103	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD6519	Phase 2
0.6313	Remote Similarity	NPD1716	Phase 3
0.6311	Remote Similarity	NPD4003	Phase 3
0.6306	Remote Similarity	NPD4113	Discontinued
0.6304	Remote Similarity	NPD8255	Phase 2
0.6304	Remote Similarity	NPD6289	Clinical (unspecified phase)
0.6301	Remote Similarity	NPD6461	Clinical (unspecified phase)
0.6301	Remote Similarity	NPD7132	Clinical (unspecified phase)
0.629	Remote Similarity	NPD3154	Approved
0.629	Remote Similarity	NPD3153	Approved
0.6284	Remote Similarity	NPD2169	Clinical (unspecified phase)
0.6284	Remote Similarity	NPD1717	Clinical (unspecified phase)
0.6273	Remote Similarity	NPD7280	Phase 3
0.6273	Remote Similarity	NPD7281	Phase 3
0.6272	Remote Similarity	NPD7811	Phase 3
0.6272	Remote Similarity	NPD7810	Phase 3
0.627	Remote Similarity	NPD7967	Discontinued
0.6262	Remote Similarity	NPD8330	Clinical (unspecified phase)
0.6261	Remote Similarity	NPD3120	Approved
0.6261	Remote Similarity	NPD5545	Phase 2
0.6261	Remote Similarity	NPD3119	Phase 1
0.6245	Remote Similarity	NPD5542	Phase 2
0.6245	Remote Similarity	NPD8359	Phase 2
0.6244	Remote Similarity	NPD6853	Approved
0.6244	Remote Similarity	NPD6851	Approved
0.6244	Remote Similarity	NPD1413	Approved
0.6244	Remote Similarity	NPD6045	Phase 3
0.6244	Remote Similarity	NPD1414	Approved
0.6239	Remote Similarity	NPD6312	Discontinued
0.623	Remote Similarity	NPD3259	Approved
0.6226	Remote Similarity	NPD7963	Phase 3
0.6223	Remote Similarity	NPD7583	Approved
0.6211	Remote Similarity	NPD7667	Clinical (unspecified phase)
0.6204	Remote Similarity	NPD5858	Discontinued
0.6199	Remote Similarity	NPD7877	Suspended
0.6197	Remote Similarity	NPD7585	Approved
0.6195	Remote Similarity	NPD5150	Phase 2
0.619	Remote Similarity	NPD2498	Approved
0.619	Remote Similarity	NPD6863	Phase 2
0.6188	Remote Similarity	NPD6793	Clinical (unspecified phase)
0.6186	Remote Similarity	NPD7608	Discontinued
0.6186	Remote Similarity	NPD4606	Clinical (unspecified phase)
0.6175	Remote Similarity	NPD5602	Clinical (unspecified phase)
0.6168	Remote Similarity	NPD2162	Clinical (unspecified phase)
0.6163	Remote Similarity	NPD4328	Approved
0.6161	Remote Similarity	NPD5773	Approved
0.6161	Remote Similarity	NPD5620	Clinical (unspecified phase)
0.6161	Remote Similarity	NPD4157	Discontinued
0.6161	Remote Similarity	NPD5772	Approved
0.6161	Remote Similarity	NPD6060	Clinical (unspecified phase)
0.616	Remote Similarity	NPD7827	Phase 1
0.6157	Remote Similarity	NPD4083	Discontinued
0.6157	Remote Similarity	NPD2388	Discontinued
0.6157	Remote Similarity	NPD6981	Phase 2
0.6154	Remote Similarity	NPD6296	Discontinued
0.6154	Remote Similarity	NPD3542	Clinical (unspecified phase)
0.6151	Remote Similarity	NPD6983	Approved
0.6147	Remote Similarity	NPD6238	Discontinued
0.6143	Remote Similarity	NPD980	Clinical (unspecified phase)
0.6143	Remote Similarity	NPD3274	Phase 2
0.6142	Remote Similarity	NPD7792	Phase 1
0.6141	Remote Similarity	NPD5496	Approved
0.6139	Remote Similarity	NPD3656	Approved
0.6137	Remote Similarity	NPD6644	Discontinued
0.6136	Remote Similarity	NPD6211	Clinical (unspecified phase)
0.6133	Remote Similarity	NPD8324	Phase 2
0.6133	Remote Similarity	NPD7235	Clinical (unspecified phase)
0.6126	Remote Similarity	NPD8116	Phase 3
0.6126	Remote Similarity	NPD8117	Approved
0.6123	Remote Similarity	NPD4590	Approved
0.6123	Remote Similarity	NPD4591	Clinical (unspecified phase)
0.6121	Remote Similarity	NPD4971	Clinical (unspecified phase)
0.6121	Remote Similarity	NPD6511	Phase 1
0.6121	Remote Similarity	NPD6510	Phase 1
0.6119	Remote Similarity	NPD3965	Phase 1
0.6119	Remote Similarity	NPD5334	Clinical (unspecified phase)
0.6114	Remote Similarity	NPD6621	Clinical (unspecified phase)
0.6113	Remote Similarity	NPD7589	Clinical (unspecified phase)
0.6106	Remote Similarity	NPD7131	Phase 3
0.6102	Remote Similarity	NPD3591	Approved
0.6102	Remote Similarity	NPD3592	Approved
0.6093	Remote Similarity	NPD2904	Discontinued
0.6093	Remote Similarity	NPD2042	Clinical (unspecified phase)
0.6093	Remote Similarity	NPD2041	Clinical (unspecified phase)
0.6091	Remote Similarity	NPD5900	Clinical (unspecified phase)
0.6089	Remote Similarity	NPD5558	Clinical (unspecified phase)
0.6089	Remote Similarity	NPD8067	Phase 3
0.6085	Remote Similarity	NPD7972	Discontinued
0.6079	Remote Similarity	NPD3601	Discontinued
0.6075	Remote Similarity	NPD3453	Discontinued
0.6074	Remote Similarity	NPD3258	Approved
0.6068	Remote Similarity	NPD5055	Clinical (unspecified phase)
0.6065	Remote Similarity	NPD2680	Approved
0.6065	Remote Similarity	NPD6107	Approved
0.6065	Remote Similarity	NPD2681	Approved
0.6064	Remote Similarity	NPD7796	Approved
0.6064	Remote Similarity	NPD7797	Approved
0.6063	Remote Similarity	NPD6496	Clinical (unspecified phase)
0.6063	Remote Similarity	NPD6297	Approved
0.6063	Remote Similarity	NPD6184	Discontinued
0.6059	Remote Similarity	NPD5845	Phase 2
0.6056	Remote Similarity	NPD3558	Approved
0.6056	Remote Similarity	NPD3560	Approved
0.6056	Remote Similarity	NPD7318	Phase 3
0.6056	Remote Similarity	NPD3557	Approved
0.6056	Remote Similarity	NPD3559	Clinical (unspecified phase)
0.6056	Remote Similarity	NPD3556	Approved
0.6056	Remote Similarity	NPD6063	Approved
0.6055	Remote Similarity	NPD2246	Approved
0.6055	Remote Similarity	NPD6365	Clinical (unspecified phase)
0.6055	Remote Similarity	NPD2248	Approved
0.6052	Remote Similarity	NPD5848	Clinical (unspecified phase)
0.6052	Remote Similarity	NPD3106	Clinical (unspecified phase)
0.605	Remote Similarity	NPD4206	Approved
0.6047	Remote Similarity	NPD7886	Phase 2
0.6047	Remote Similarity	NPD7560	Approved
0.6047	Remote Similarity	NPD7885	Phase 2
0.6045	Remote Similarity	NPD5312	Approved
0.6045	Remote Similarity	NPD5521	Clinical (unspecified phase)
0.6045	Remote Similarity	NPD5670	Approved
0.6045	Remote Similarity	NPD5313	Approved
0.6045	Remote Similarity	NPD3793	Phase 3
0.6044	Remote Similarity	NPD3857	Clinical (unspecified phase)
0.6043	Remote Similarity	NPD7174	Clinical (unspecified phase)
0.604	Remote Similarity	NPD6625	Approved
0.6038	Remote Similarity	NPD3812	Clinical (unspecified phase)
0.6036	Remote Similarity	NPD7149	Clinical (unspecified phase)
0.6035	Remote Similarity	NPD3808	Clinical (unspecified phase)
0.6034	Remote Similarity	NPD4917	Discontinued
0.6032	Remote Similarity	NPD7412	Clinical (unspecified phase)
0.6031	Remote Similarity	NPD8461	Discontinued
0.6029	Remote Similarity	NPD3655	Clinical (unspecified phase)
0.6028	Remote Similarity	NPD2995	Approved
0.6027	Remote Similarity	NPD3366	Approved
0.6026	Remote Similarity	NPD6669	Phase 2
0.6025	Remote Similarity	NPD6560	Approved
0.6025	Remote Similarity	NPD6298	Discontinued
0.6024	Remote Similarity	NPD7432	Phase 2
0.6024	Remote Similarity	NPD1867	Approved
0.6018	Remote Similarity	NPD5557	Phase 1
0.6018	Remote Similarity	NPD2425	Phase 1
0.601	Remote Similarity	NPD4123	Phase 3
0.601	Remote Similarity	NPD6032	Approved
0.601	Remote Similarity	NPD8389	Clinical (unspecified phase)
0.6009	Remote Similarity	NPD1361	Discontinued
0.6009	Remote Similarity	NPD3634	Approved
0.6009	Remote Similarity	NPD3936	Clinical (unspecified phase)
0.6009	Remote Similarity	NPD3633	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