NPASS Compound

Structure

NPC37957 OpenBabel07101719252D 34 40 0 0 1 0 0 0 0 0999 V2000 -6.6989 1.3591 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4543 2.2885 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0856 -2.9398 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5031 -2.6034 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2463 -0.9341 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6011 0.7353 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2953 1.3603 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2662 -0.1307 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6973 -1.6897 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9603 0.4943 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6973 -0.1784 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.8681 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3778 0.1580 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7953 -0.1784 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1836 1.0716 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8089 -1.4011 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.6837 -0.4670 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6973 -0.1784 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8089 -0.4670 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7953 -1.6897 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7661 1.4080 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6973 -1.6897 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8089 -1.4011 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.2463 -0.9341 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8089 -0.4670 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.6837 -1.4011 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 0.8089 -0.4670 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.9859 0.7100 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.4268 0.4670 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5067 -2.5781 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.9341 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.8778 1.6966 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 22 1 0 0 0 0 2 22 1 0 0 0 0 3 23 1 0 0 0 0 4 23 1 0 0 0 0 5 9 1 0 0 0 0 5 11 1 0 0 0 0 6 7 2 0 0 0 0 6 14 1 0 0 0 0 7 15 1 0 0 0 0 8 10 2 0 0 0 0 8 13 1 0 0 0 0 9 24 1 0 0 0 0 10 22 1 0 0 0 0 11 29 1 0 0 0 0 12 16 1 0 0 0 0 12 24 1 0 0 0 0 13 15 2 0 0 0 0 13 17 1 0 0 0 0 14 17 2 0 0 0 0 15 34 1 0 0 0 0 16 23 1 0 0 0 0 16 26 1 1 0 0 0 17 27 1 0 0 0 0 18 25 1 1 0 0 0 18 26 1 0 0 0 0 18 30 1 0 0 0 0 19 28 2 0 0 0 0 19 31 1 0 0 0 0 20 25 1 0 0 0 0 20 27 2 0 0 0 0 20 32 1 0 0 0 0 21 29 1 0 0 0 0 21 33 2 0 0 0 0 22 34 1 0 0 0 0 23 25 1 0 0 0 0 24 19 1 6 0 0 0 24 29 1 0 0 0 0 25 14 1 1 0 0 0 26 21 1 1 0 0 0 26 28 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	463.21
Volume:	456.843
LogP:	3.234
LogD:	2.712
LogS:	-4.219
# Rotatable Bonds:	0
TPSA:	107.97
# H-Bond Aceptor:	8
# H-Bond Donor:	3
# Rings:	8
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.543
Synthetic Accessibility Score:	6.695
Fsp3:	0.577
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.275
MDCK Permeability:	2.65012240561191e-05
Pgp-inhibitor:	0.971
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.074
20% Bioavailability (F20%):	0.78
30% Bioavailability (F30%):	0.804

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.308
Plasma Protein Binding (PPB):	82.021484375%
Volume Distribution (VD):	0.962
Pgp-substrate:	16.024568557739258%

ADMET: Metabolism

CYP1A2-inhibitor:	0.008
CYP1A2-substrate:	0.386
CYP2C19-inhibitor:	0.087
CYP2C19-substrate:	0.896
CYP2C9-inhibitor:	0.412
CYP2C9-substrate:	0.283
CYP2D6-inhibitor:	0.039
CYP2D6-substrate:	0.14
CYP3A4-inhibitor:	0.871
CYP3A4-substrate:	0.903

ADMET: Excretion

Clearance (CL):	5.194
Half-life (T1/2):	0.49

ADMET: Toxicity

hERG Blockers:	0.019
Human Hepatotoxicity (H-HT):	0.828
Drug-inuced Liver Injury (DILI):	0.883
AMES Toxicity:	0.829
Rat Oral Acute Toxicity:	0.989
Maximum Recommended Daily Dose:	0.963
Skin Sensitization:	0.169
Carcinogencity:	0.941
Eye Corrosion:	0.003
Eye Irritation:	0.005
Respiratory Toxicity:	0.789

Download Data

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

Natural Product: NPC37957

Natural Product ID:	NPC37957
*Common Name:**	CFJMAERFDLWMJL-DGRAJDSTSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	CFJMAERFDLWMJL-DGRAJDSTSA-N
Standard InCHI:	InChI=1S/C26H29N3O5/c1-22(2)10-8-13-15(34-22)7-6-14-17(13)27-20(32)25(14)18(30)26-16(23(25,3)4)12-24(19(31)28-26)9-5-11-29(24)21(26)33/h6-8,10,16,18,30H,5,9,11-12H2,1-4H3,(H,27,32)(H,28,31)/t16-,18+,24-,25-,26+/m0/s1
SMILES:	OC1=Nc2c([C@@]31[C@@H](O)[C@@]14[C@H](C3(C)C)C[C@@]3(C(=N1)O)N(C4=O)CCC3)ccc1c2C=CC(O1)(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2375796
PubChem CID:	71712815
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000123] Benzopyrans [CHEMONTID:0003410] 1-benzopyrans [CHEMONTID:0003522] 2,2-dimethyl-1-benzopyrans

*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
NPO32643	aspergillus westerdijkiae dffscs013	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23701598]

☑ 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	4

Activity Type	# Activity
Cell Line	4

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[546155]
NPT111	Cell Line	K562	Homo sapiens	IC50	=	53000.0	nM	PMID[546155]
NPT116	Cell Line	HL-60	Homo sapiens	IC50	>	10000.0	nM	PMID[546155]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	10000.0	nM	PMID[546155]

☑ 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 NPC37957 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	355
0.1-0.2	1626
0.2-0.3	5268
0.3-0.4	12670
0.4-0.5	14734
0.5-0.6	7209
0.6-0.7	769
0.7-0.8	40
0.8-0.85	15
0.85-0.9	6
0.9-0.95	3
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9796	High Similarity	NPC153923
0.9286	High Similarity	NPC205926
0.9104	High Similarity	NPC49583
0.8627	High Similarity	NPC476651
0.8326	Intermediate Similarity	NPC266994
0.8249	Intermediate Similarity	NPC74216
0.8186	Intermediate Similarity	NPC71539
0.8186	Intermediate Similarity	NPC250960
0.8109	Intermediate Similarity	NPC204970
0.8075	Intermediate Similarity	NPC470001
0.8075	Intermediate Similarity	NPC470002
0.8045	Intermediate Similarity	NPC470821
0.7745	Intermediate Similarity	NPC174629
0.7735	Intermediate Similarity	NPC189079
0.7692	Intermediate Similarity	NPC133609
0.7636	Intermediate Similarity	NPC219397
0.7612	Intermediate Similarity	NPC39822
0.7489	Intermediate Similarity	NPC46259
0.7379	Intermediate Similarity	NPC473007
0.7361	Intermediate Similarity	NPC14339
0.7339	Intermediate Similarity	NPC131486
0.7321	Intermediate Similarity	NPC473008
0.7286	Intermediate Similarity	NPC28510
0.7256	Intermediate Similarity	NPC67904
0.7251	Intermediate Similarity	NPC473004
0.7238	Intermediate Similarity	NPC473569
0.7207	Intermediate Similarity	NPC127996
0.719	Intermediate Similarity	NPC244543
0.7162	Intermediate Similarity	NPC82541
0.7149	Intermediate Similarity	NPC477160
0.711	Intermediate Similarity	NPC473005
0.7093	Intermediate Similarity	NPC288110
0.7093	Intermediate Similarity	NPC222046
0.7083	Intermediate Similarity	NPC100863
0.7061	Intermediate Similarity	NPC318525
0.7061	Intermediate Similarity	NPC10653
0.7039	Intermediate Similarity	NPC477397
0.7035	Intermediate Similarity	NPC234772
0.7023	Intermediate Similarity	NPC230313
0.7014	Intermediate Similarity	NPC477161
0.7013	Intermediate Similarity	NPC122886
0.6978	Remote Similarity	NPC159815
0.6975	Remote Similarity	NPC470784
0.6975	Remote Similarity	NPC474183
0.6974	Remote Similarity	NPC77777
0.6953	Remote Similarity	NPC473458
0.6953	Remote Similarity	NPC471513
0.6944	Remote Similarity	NPC243626
0.6941	Remote Similarity	NPC138830
0.6923	Remote Similarity	NPC473460
0.6906	Remote Similarity	NPC79130
0.6904	Remote Similarity	NPC470785
0.6904	Remote Similarity	NPC151171
0.6903	Remote Similarity	NPC10732
0.6901	Remote Similarity	NPC477393
0.6892	Remote Similarity	NPC87714
0.6889	Remote Similarity	NPC14390
0.6888	Remote Similarity	NPC469722
0.6888	Remote Similarity	NPC477395
0.688	Remote Similarity	NPC470480
0.6878	Remote Similarity	NPC474077
0.6864	Remote Similarity	NPC127178
0.6862	Remote Similarity	NPC184680
0.686	Remote Similarity	NPC210415
0.686	Remote Similarity	NPC276993
0.686	Remote Similarity	NPC293255
0.686	Remote Similarity	NPC298851
0.686	Remote Similarity	NPC181138
0.686	Remote Similarity	NPC21752
0.6844	Remote Similarity	NPC477396
0.6837	Remote Similarity	NPC474059
0.6837	Remote Similarity	NPC283207
0.6835	Remote Similarity	NPC308709
0.6826	Remote Similarity	NPC303658
0.682	Remote Similarity	NPC203972
0.6798	Remote Similarity	NPC217903
0.6798	Remote Similarity	NPC473006
0.6797	Remote Similarity	NPC108826
0.6794	Remote Similarity	NPC211713
0.6794	Remote Similarity	NPC88378
0.678	Remote Similarity	NPC254700
0.678	Remote Similarity	NPC469479
0.6776	Remote Similarity	NPC262725
0.677	Remote Similarity	NPC471561
0.677	Remote Similarity	NPC293347
0.6767	Remote Similarity	NPC128115
0.6766	Remote Similarity	NPC476436
0.6757	Remote Similarity	NPC232600
0.6756	Remote Similarity	NPC198160
0.6754	Remote Similarity	NPC116178
0.6749	Remote Similarity	NPC97380
0.6749	Remote Similarity	NPC63210
0.6749	Remote Similarity	NPC243673
0.6749	Remote Similarity	NPC310403
0.6749	Remote Similarity	NPC263709
0.6749	Remote Similarity	NPC148468
0.6729	Remote Similarity	NPC315542
0.6726	Remote Similarity	NPC311357
0.6725	Remote Similarity	NPC321166
0.6723	Remote Similarity	NPC115588
0.6713	Remote Similarity	NPC217294
0.6699	Remote Similarity	NPC52059
0.6699	Remote Similarity	NPC470069
0.6696	Remote Similarity	NPC168250
0.6683	Remote Similarity	NPC67080
0.6681	Remote Similarity	NPC264176
0.668	Remote Similarity	NPC291173
0.6667	Remote Similarity	NPC329731
0.6667	Remote Similarity	NPC470484
0.6667	Remote Similarity	NPC4910
0.6667	Remote Similarity	NPC470485
0.6667	Remote Similarity	NPC473422
0.6667	Remote Similarity	NPC197125
0.6653	Remote Similarity	NPC477394
0.6652	Remote Similarity	NPC272706
0.6652	Remote Similarity	NPC30749
0.6652	Remote Similarity	NPC161804
0.6651	Remote Similarity	NPC206061
0.6651	Remote Similarity	NPC22476
0.6651	Remote Similarity	NPC475421
0.6639	Remote Similarity	NPC194740
0.6638	Remote Similarity	NPC126556
0.6638	Remote Similarity	NPC148124
0.6637	Remote Similarity	NPC195787
0.6637	Remote Similarity	NPC246140
0.6636	Remote Similarity	NPC470112
0.6636	Remote Similarity	NPC470903
0.6636	Remote Similarity	NPC167763
0.6635	Remote Similarity	NPC476441
0.6625	Remote Similarity	NPC476429
0.6623	Remote Similarity	NPC314817
0.6623	Remote Similarity	NPC316297
0.6623	Remote Similarity	NPC66191
0.6623	Remote Similarity	NPC189661
0.6622	Remote Similarity	NPC41216
0.6618	Remote Similarity	NPC153694
0.6618	Remote Similarity	NPC71205
0.6618	Remote Similarity	NPC211525
0.6609	Remote Similarity	NPC305542
0.6609	Remote Similarity	NPC470482
0.6609	Remote Similarity	NPC470481
0.6606	Remote Similarity	NPC303214
0.6604	Remote Similarity	NPC127082
0.6602	Remote Similarity	NPC472121
0.6601	Remote Similarity	NPC161827
0.6597	Remote Similarity	NPC248903
0.6596	Remote Similarity	NPC99724
0.6591	Remote Similarity	NPC471825
0.6591	Remote Similarity	NPC260909
0.659	Remote Similarity	NPC21425
0.6582	Remote Similarity	NPC231924
0.6578	Remote Similarity	NPC15987
0.6575	Remote Similarity	NPC470483
0.657	Remote Similarity	NPC293164
0.657	Remote Similarity	NPC471394
0.6567	Remote Similarity	NPC305984
0.6562	Remote Similarity	NPC475489
0.6561	Remote Similarity	NPC184933
0.6561	Remote Similarity	NPC59827
0.6558	Remote Similarity	NPC98197
0.6555	Remote Similarity	NPC26928
0.6555	Remote Similarity	NPC469505
0.6553	Remote Similarity	NPC476069
0.655	Remote Similarity	NPC475133
0.6547	Remote Similarity	NPC234933
0.6545	Remote Similarity	NPC469452
0.6544	Remote Similarity	NPC291759
0.6542	Remote Similarity	NPC166169
0.654	Remote Similarity	NPC475565
0.654	Remote Similarity	NPC475349
0.654	Remote Similarity	NPC137627
0.654	Remote Similarity	NPC476425
0.654	Remote Similarity	NPC475292
0.6535	Remote Similarity	NPC478075
0.653	Remote Similarity	NPC22689
0.653	Remote Similarity	NPC105055
0.6525	Remote Similarity	NPC329830
0.6525	Remote Similarity	NPC128476
0.6513	Remote Similarity	NPC19175
0.6511	Remote Similarity	NPC475609
0.6509	Remote Similarity	NPC476227
0.6504	Remote Similarity	NPC471436
0.6502	Remote Similarity	NPC237901
0.6502	Remote Similarity	NPC66909
0.6502	Remote Similarity	NPC195788
0.65	Remote Similarity	NPC203628
0.6498	Remote Similarity	NPC133591
0.6498	Remote Similarity	NPC299806
0.6498	Remote Similarity	NPC102760
0.6498	Remote Similarity	NPC106593
0.6496	Remote Similarity	NPC195636
0.6495	Remote Similarity	NPC126515
0.6495	Remote Similarity	NPC472331
0.6495	Remote Similarity	NPC274002
0.6494	Remote Similarity	NPC471532
0.6494	Remote Similarity	NPC67401
0.6492	Remote Similarity	NPC329932
0.649	Remote Similarity	NPC472923
0.6488	Remote Similarity	NPC473486
0.6488	Remote Similarity	NPC475316

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 NPC37957 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	211
0.1-0.2	592
0.2-0.3	878
0.3-0.4	2229
0.4-0.5	3016
0.5-0.6	2020
0.6-0.7	204
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
0.7014	Intermediate Similarity	NPD7174	Clinical (unspecified phase)
0.7014	Intermediate Similarity	NPD8161	Suspended
0.6972	Remote Similarity	NPD7811	Phase 3
0.6972	Remote Similarity	NPD7810	Phase 3
0.6963	Remote Similarity	NPD6656	Clinical (unspecified phase)
0.6952	Remote Similarity	NPD7132	Clinical (unspecified phase)
0.6798	Remote Similarity	NPD5967	Approved
0.6791	Remote Similarity	NPD6608	Clinical (unspecified phase)
0.6789	Remote Similarity	NPD4771	Phase 2
0.6781	Remote Similarity	NPD6824	Clinical (unspecified phase)
0.6766	Remote Similarity	NPD5617	Suspended
0.6715	Remote Similarity	NPD4986	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD2042	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD2041	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD2904	Discontinued
0.6653	Remote Similarity	NPD7821	Clinical (unspecified phase)
0.6651	Remote Similarity	NPD2215	Approved
0.6651	Remote Similarity	NPD2216	Approved
0.6627	Remote Similarity	NPD8461	Discontinued
0.6623	Remote Similarity	NPD3591	Approved
0.6623	Remote Similarity	NPD3592	Approved
0.661	Remote Similarity	NPD7820	Phase 3
0.6607	Remote Similarity	NPD7566	Clinical (unspecified phase)
0.6598	Remote Similarity	NPD7025	Clinical (unspecified phase)
0.6593	Remote Similarity	NPD3298	Approved
0.6591	Remote Similarity	NPD8460	Approved
0.6591	Remote Similarity	NPD8459	Approved
0.656	Remote Similarity	NPD5620	Clinical (unspecified phase)
0.6558	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6555	Remote Similarity	NPD7426	Phase 1
0.6553	Remote Similarity	NPD6063	Approved
0.6542	Remote Similarity	NPD4981	Phase 2
0.6533	Remote Similarity	NPD6321	Discontinued
0.6524	Remote Similarity	NPD5561	Approved
0.6524	Remote Similarity	NPD5562	Approved
0.6522	Remote Similarity	NPD8255	Phase 2
0.6518	Remote Similarity	NPD3297	Approved
0.6502	Remote Similarity	NPD2974	Approved
0.6502	Remote Similarity	NPD4605	Approved
0.6502	Remote Similarity	NPD8466	Approved
0.6502	Remote Similarity	NPD8465	Approved
0.6502	Remote Similarity	NPD2973	Approved
0.6502	Remote Similarity	NPD8467	Approved
0.6502	Remote Similarity	NPD4604	Approved
0.6502	Remote Similarity	NPD2975	Approved
0.6495	Remote Similarity	NPD5900	Clinical (unspecified phase)
0.6493	Remote Similarity	NPD2388	Discontinued
0.6489	Remote Similarity	NPD4580	Approved
0.6471	Remote Similarity	NPD3601	Discontinued
0.6471	Remote Similarity	NPD3912	Discontinued
0.6462	Remote Similarity	NPD8363	Approved
0.6462	Remote Similarity	NPD8364	Approved
0.6453	Remote Similarity	NPD7131	Phase 3
0.645	Remote Similarity	NPD5645	Phase 3
0.6449	Remote Similarity	NPD7048	Phase 3
0.6449	Remote Similarity	NPD5521	Clinical (unspecified phase)
0.6447	Remote Similarity	NPD3946	Clinical (unspecified phase)
0.6439	Remote Similarity	NPD8429	Approved
0.6439	Remote Similarity	NPD8428	Approved
0.6439	Remote Similarity	NPD8427	Approved
0.6438	Remote Similarity	NPD3120	Approved
0.6438	Remote Similarity	NPD3119	Phase 1
0.6438	Remote Similarity	NPD3863	Clinical (unspecified phase)
0.6436	Remote Similarity	NPD7020	Approved
0.6436	Remote Similarity	NPD7019	Approved
0.6435	Remote Similarity	NPD8027	Approved
0.6429	Remote Similarity	NPD7238	Clinical (unspecified phase)
0.6425	Remote Similarity	NPD5525	Clinical (unspecified phase)
0.6417	Remote Similarity	NPD7186	Phase 3
0.6417	Remote Similarity	NPD8492	Approved
0.6415	Remote Similarity	NPD8051	Clinical (unspecified phase)
0.6414	Remote Similarity	NPD3437	Discontinued
0.6412	Remote Similarity	NPD8365	Clinical (unspecified phase)
0.6405	Remote Similarity	NPD7589	Clinical (unspecified phase)
0.6404	Remote Similarity	NPD8426	Approved
0.6404	Remote Similarity	NPD7497	Discontinued
0.6404	Remote Similarity	NPD8425	Approved
0.6404	Remote Similarity	NPD3802	Phase 3
0.64	Remote Similarity	NPD8359	Phase 2
0.6391	Remote Similarity	NPD8107	Approved
0.639	Remote Similarity	NPD5811	Approved
0.6389	Remote Similarity	NPD6654	Clinical (unspecified phase)
0.6388	Remote Similarity	NPD3452	Approved
0.6388	Remote Similarity	NPD2493	Approved
0.6388	Remote Similarity	NPD3450	Approved
0.6388	Remote Similarity	NPD6238	Discontinued
0.6388	Remote Similarity	NPD2494	Approved
0.6384	Remote Similarity	NPD7667	Clinical (unspecified phase)
0.6383	Remote Similarity	NPD8149	Discontinued
0.638	Remote Similarity	NPD2845	Phase 2
0.638	Remote Similarity	NPD2843	Phase 2
0.6379	Remote Similarity	NPD3441	Approved
0.6379	Remote Similarity	NPD3442	Approved
0.6377	Remote Similarity	NPD8108	Approved
0.6376	Remote Similarity	NPD4583	Approved
0.6376	Remote Similarity	NPD6644	Discontinued
0.6376	Remote Similarity	NPD4040	Phase 1
0.6376	Remote Similarity	NPD4582	Approved
0.6376	Remote Similarity	NPD5102	Clinical (unspecified phase)
0.6372	Remote Similarity	NPD5547	Clinical (unspecified phase)
0.6372	Remote Similarity	NPD5312	Approved
0.6372	Remote Similarity	NPD6874	Approved
0.6372	Remote Similarity	NPD3050	Clinical (unspecified phase)
0.6372	Remote Similarity	NPD5313	Approved
0.6371	Remote Similarity	NPD5496	Approved
0.6371	Remote Similarity	NPD6790	Phase 1
0.6368	Remote Similarity	NPD7608	Discontinued
0.6368	Remote Similarity	NPD7315	Approved
0.636	Remote Similarity	NPD3106	Clinical (unspecified phase)
0.636	Remote Similarity	NPD6997	Phase 2
0.6356	Remote Similarity	NPD3949	Clinical (unspecified phase)
0.6351	Remote Similarity	NPD6037	Discontinued
0.6351	Remote Similarity	NPD2490	Approved
0.6351	Remote Similarity	NPD2488	Approved
0.6346	Remote Similarity	NPD6668	Clinical (unspecified phase)
0.6332	Remote Similarity	NPD4004	Approved
0.6332	Remote Similarity	NPD4002	Approved
0.6332	Remote Similarity	NPD7064	Clinical (unspecified phase)
0.6331	Remote Similarity	NPD7560	Approved
0.6329	Remote Similarity	NPD6568	Discontinued
0.6325	Remote Similarity	NPD7178	Clinical (unspecified phase)
0.6324	Remote Similarity	NPD8367	Approved
0.6323	Remote Similarity	NPD5587	Approved
0.6321	Remote Similarity	NPD6457	Approved
0.632	Remote Similarity	NPD4946	Phase 2
0.6318	Remote Similarity	NPD3153	Approved
0.6318	Remote Similarity	NPD7556	Discontinued
0.6318	Remote Similarity	NPD3154	Approved
0.6316	Remote Similarity	NPD3416	Discontinued
0.6313	Remote Similarity	NPD3823	Discontinued
0.6313	Remote Similarity	NPD6879	Phase 2
0.6313	Remote Similarity	NPD6878	Phase 2
0.6311	Remote Similarity	NPD7284	Clinical (unspecified phase)
0.6311	Remote Similarity	NPD8249	Clinical (unspecified phase)
0.6308	Remote Similarity	NPD2246	Approved
0.6308	Remote Similarity	NPD2248	Approved
0.6301	Remote Similarity	NPD2971	Approved
0.6301	Remote Similarity	NPD7281	Phase 3
0.6301	Remote Similarity	NPD7280	Phase 3
0.6301	Remote Similarity	NPD2968	Approved
0.63	Remote Similarity	NPD3655	Clinical (unspecified phase)
0.6296	Remote Similarity	NPD3793	Phase 3
0.6296	Remote Similarity	NPD3965	Phase 1
0.629	Remote Similarity	NPD8103	Clinical (unspecified phase)
0.6287	Remote Similarity	NPD3940	Clinical (unspecified phase)
0.6284	Remote Similarity	NPD6104	Discontinued
0.6284	Remote Similarity	NPD7149	Clinical (unspecified phase)
0.6282	Remote Similarity	NPD1945	Phase 1
0.628	Remote Similarity	NPD6716	Phase 1
0.6278	Remote Similarity	NPD6504	Approved
0.6278	Remote Similarity	NPD3808	Clinical (unspecified phase)
0.6278	Remote Similarity	NPD6505	Approved
0.6277	Remote Similarity	NPD7607	Clinical (unspecified phase)
0.6273	Remote Similarity	NPD6853	Approved
0.6273	Remote Similarity	NPD6851	Approved
0.6273	Remote Similarity	NPD6021	Clinical (unspecified phase)
0.6272	Remote Similarity	NPD6519	Phase 2
0.6271	Remote Similarity	NPD7559	Phase 2
0.6268	Remote Similarity	NPD6060	Clinical (unspecified phase)
0.6268	Remote Similarity	NPD5294	Clinical (unspecified phase)
0.6262	Remote Similarity	NPD814	Clinical (unspecified phase)
0.6261	Remote Similarity	NPD1339	Discontinued
0.6261	Remote Similarity	NPD7291	Discontinued
0.6261	Remote Similarity	NPD8025	Phase 2
0.6261	Remote Similarity	NPD6198	Phase 1
0.626	Remote Similarity	NPD6525	Clinical (unspecified phase)
0.6256	Remote Similarity	NPD7190	Clinical (unspecified phase)
0.625	Remote Similarity	NPD5937	Approved
0.625	Remote Similarity	NPD7584	Approved
0.625	Remote Similarity	NPD7118	Clinical (unspecified phase)
0.6245	Remote Similarity	NPD7475	Clinical (unspecified phase)
0.6244	Remote Similarity	NPD7485	Phase 3
0.6244	Remote Similarity	NPD7484	Phase 3
0.6239	Remote Similarity	NPD4362	Clinical (unspecified phase)
0.6239	Remote Similarity	NPD4900	Clinical (unspecified phase)
0.6239	Remote Similarity	NPD4997	Clinical (unspecified phase)
0.6239	Remote Similarity	NPD6297	Approved
0.6239	Remote Similarity	NPD4361	Phase 2
0.6239	Remote Similarity	NPD5726	Clinical (unspecified phase)
0.6227	Remote Similarity	NPD4078	Clinical (unspecified phase)
0.6224	Remote Similarity	NPD8311	Discontinued
0.6223	Remote Similarity	NPD2907	Approved
0.6223	Remote Similarity	NPD2906	Approved
0.6222	Remote Similarity	NPD4539	Phase 1
0.6221	Remote Similarity	NPD5334	Clinical (unspecified phase)
0.622	Remote Similarity	NPD7031	Phase 1
0.6217	Remote Similarity	NPD5848	Clinical (unspecified phase)
0.6216	Remote Similarity	NPD4951	Discontinued
0.6213	Remote Similarity	NPD6567	Clinical (unspecified phase)
0.6207	Remote Similarity	NPD6905	Phase 2
0.6203	Remote Similarity	NPD4897	Phase 2
0.62	Remote Similarity	NPD8016	Phase 3
0.62	Remote Similarity	NPD8017	Clinical (unspecified phase)
0.6199	Remote Similarity	NPD6556	Clinical (unspecified phase)
0.6198	Remote Similarity	NPD7278	Phase 2
0.6198	Remote Similarity	NPD7279	Phase 2
0.6195	Remote Similarity	NPD4363	Phase 3
0.6195	Remote Similarity	NPD4360	Phase 2
0.6194	Remote Similarity	NPD6625	Approved
0.6194	Remote Similarity	NPD4373	Phase 2

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