NPASS Compound

Structure

NPC476250 OpenBabel07101719242D 26 31 0 0 1 0 0 0 0 0999 V2000 4.2376 -4.0808 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0083 -2.4604 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0924 -1.8527 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4034 -4.5624 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0123 -2.8490 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2376 -3.1175 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4185 -3.2687 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4034 -2.6358 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0538 -2.5276 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6037 -1.6936 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1937 -1.7569 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5691 -3.1175 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8442 -4.1506 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 2.3437 -3.8479 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 2.8834 -1.3857 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3377 -3.6273 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 4.9535 -2.4729 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4309 -2.9050 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 3.3328 -2.9653 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 5.8958 -2.6732 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 1.6200 -1.5396 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 4.5617 -1.5929 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 2.5691 -4.0808 0.0000 N 0 3 0 0 0 0 0 0 0 0 0 0 3.9582 -4.8992 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.8402 -0.4234 0.0000 O 0 5 0 0 0 0 0 0 0 0 0 0 0.4234 -3.9307 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 4 1 0 0 0 0 1 6 1 0 0 0 0 2 3 1 0 0 0 0 2 18 1 0 0 0 0 3 21 1 0 0 0 0 4 23 1 0 0 0 0 5 7 2 0 0 0 0 5 18 1 0 0 0 0 6 8 2 0 0 0 0 6 17 1 0 0 0 0 7 14 1 0 0 0 0 7 19 1 0 0 0 0 8 10 1 0 0 0 0 8 12 1 0 0 0 0 9 11 2 0 0 0 0 9 12 1 0 0 0 0 9 18 1 0 0 0 0 10 15 2 0 0 0 0 10 22 1 0 0 0 0 11 15 1 0 0 0 0 11 21 1 0 0 0 0 12 23 2 0 0 0 0 13 14 1 0 0 0 0 13 16 1 0 0 0 0 13 23 1 0 0 0 0 14 24 1 0 0 0 0 15 25 1 0 0 0 0 16 18 1 0 0 0 0 16 26 1 0 0 0 0 17 20 1 0 0 0 0 17 22 2 0 0 0 0 M CHG 2 23 1 25 -1 M END $$$$

Physi-Chem Properties

Molecular Weight:	478.95
Volume:	350.655
LogP:	0.876
LogD:	1.035
LogS:	-1.413
# Rotatable Bonds:	0
TPSA:	92.68
# H-Bond Aceptor:	6
# H-Bond Donor:	3
# Rings:	6
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.441
Synthetic Accessibility Score:	7.596
Fsp3:	0.444
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.713
MDCK Permeability:	1.656878703215625e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.737
Human Intestinal Absorption (HIA):	0.899
20% Bioavailability (F20%):	0.41
30% Bioavailability (F30%):	0.582

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.402
Plasma Protein Binding (PPB):	80.31433868408203%
Volume Distribution (VD):	2.155
Pgp-substrate:	27.009143829345703%

ADMET: Metabolism

CYP1A2-inhibitor:	0.147
CYP1A2-substrate:	0.4
CYP2C19-inhibitor:	0.023
CYP2C19-substrate:	0.319
CYP2C9-inhibitor:	0.005
CYP2C9-substrate:	0.261
CYP2D6-inhibitor:	0.023
CYP2D6-substrate:	0.199
CYP3A4-inhibitor:	0.007
CYP3A4-substrate:	0.502

ADMET: Excretion

Clearance (CL):	1.117
Half-life (T1/2):	0.487

ADMET: Toxicity

hERG Blockers:	0.015
Human Hepatotoxicity (H-HT):	0.763
Drug-inuced Liver Injury (DILI):	0.173
AMES Toxicity:	0.182
Rat Oral Acute Toxicity:	0.99
Maximum Recommended Daily Dose:	0.949
Skin Sensitization:	0.425
Carcinogencity:	0.968
Eye Corrosion:	0.003
Eye Irritation:	0.006
Respiratory Toxicity:	0.963

Download Data

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

Natural Product: NPC476250

Natural Product ID:	NPC476250
*Common Name:**	RFJHWSPGAUAJAW-UHFFFAOYSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	RFJHWSPGAUAJAW-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C18H15Br2N3O3.ClH/c19-7-5-18-2-3-21-11-9(18)12-8-6(17(20)22-10(8)15(11)25)1-4-23(12)13(14(7)24)16(18)26;/h5,13-14,16,24,26H,1-4H2,(H,21,22,25);1H
SMILES:	BrC1=CC23CCNc4c3c3=[N+](C(C1O)C2O)CCC1=c3c(c4[O-])N=C1Br.Cl
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL558429
PubChem CID:	45266418
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001626] Phenanthrolines

*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
NPO32524	latrunculid sponges	Species	n.a.	n.a.	n.a.	South African	n.a.	PMID[15332840]

☑ 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	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT393	Cell Line	HCT-116	Homo sapiens	IC50	=	12496.0	nM	PMID[557382]

☑ 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 NPC476250 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	352
0.1-0.2	1812
0.2-0.3	11923
0.3-0.4	13729
0.4-0.5	10911
0.5-0.6	3832
0.6-0.7	137
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.6979	Remote Similarity	NPC116096
0.6772	Remote Similarity	NPC33507
0.6714	Remote Similarity	NPC477110
0.6699	Remote Similarity	NPC1464
0.6617	Remote Similarity	NPC470483
0.6611	Remote Similarity	NPC472103
0.6603	Remote Similarity	NPC477113
0.66	Remote Similarity	NPC217294
0.6552	Remote Similarity	NPC470485
0.654	Remote Similarity	NPC477111
0.654	Remote Similarity	NPC476157
0.6538	Remote Similarity	NPC470678
0.6524	Remote Similarity	NPC195787
0.6524	Remote Similarity	NPC246140
0.6481	Remote Similarity	NPC476161
0.6432	Remote Similarity	NPC98197
0.6425	Remote Similarity	NPC132874
0.6425	Remote Similarity	NPC138615
0.6425	Remote Similarity	NPC218733
0.6425	Remote Similarity	NPC265642
0.6404	Remote Similarity	NPC5630
0.6381	Remote Similarity	NPC52801
0.6364	Remote Similarity	NPC249040
0.6333	Remote Similarity	NPC469732
0.6327	Remote Similarity	NPC34508
0.6321	Remote Similarity	NPC470484
0.6298	Remote Similarity	NPC316282
0.6292	Remote Similarity	NPC184437
0.6276	Remote Similarity	NPC252590
0.627	Remote Similarity	NPC472100
0.6263	Remote Similarity	NPC477156
0.6263	Remote Similarity	NPC477157
0.6256	Remote Similarity	NPC472329
0.6256	Remote Similarity	NPC472330
0.625	Remote Similarity	NPC478032
0.6244	Remote Similarity	NPC3715
0.6244	Remote Similarity	NPC118832
0.6244	Remote Similarity	NPC47059
0.6244	Remote Similarity	NPC329708
0.6244	Remote Similarity	NPC165349
0.6244	Remote Similarity	NPC264166
0.6244	Remote Similarity	NPC274291
0.6224	Remote Similarity	NPC126481
0.6218	Remote Similarity	NPC85651
0.62	Remote Similarity	NPC232340
0.62	Remote Similarity	NPC270009
0.6188	Remote Similarity	NPC470502
0.6178	Remote Similarity	NPC477394
0.6168	Remote Similarity	NPC470500
0.6162	Remote Similarity	NPC259545
0.6161	Remote Similarity	NPC470501
0.6157	Remote Similarity	NPC18348
0.615	Remote Similarity	NPC474077
0.6143	Remote Similarity	NPC132642
0.6139	Remote Similarity	NPC192270
0.6135	Remote Similarity	NPC203628
0.6133	Remote Similarity	NPC470503
0.6129	Remote Similarity	NPC476116
0.6119	Remote Similarity	NPC94174
0.6114	Remote Similarity	NPC477112
0.6103	Remote Similarity	NPC232600
0.6101	Remote Similarity	NPC469562
0.6101	Remote Similarity	NPC220594
0.6101	Remote Similarity	NPC5145
0.61	Remote Similarity	NPC203754
0.61	Remote Similarity	NPC150048
0.61	Remote Similarity	NPC185172
0.6096	Remote Similarity	NPC264589
0.6095	Remote Similarity	NPC303214
0.6094	Remote Similarity	NPC301501
0.6093	Remote Similarity	NPC87714
0.6089	Remote Similarity	NPC476687
0.6089	Remote Similarity	NPC476685
0.6089	Remote Similarity	NPC476689
0.6082	Remote Similarity	NPC477158
0.6077	Remote Similarity	NPC78284
0.6071	Remote Similarity	NPC70172
0.607	Remote Similarity	NPC293472
0.6066	Remote Similarity	NPC77555
0.6066	Remote Similarity	NPC272706
0.6066	Remote Similarity	NPC161804
0.6065	Remote Similarity	NPC472111
0.6062	Remote Similarity	NPC469428
0.6061	Remote Similarity	NPC257354
0.6059	Remote Similarity	NPC475962
0.6054	Remote Similarity	NPC469594
0.6053	Remote Similarity	NPC475763
0.6053	Remote Similarity	NPC470126
0.6051	Remote Similarity	NPC472121
0.6051	Remote Similarity	NPC476231
0.6045	Remote Similarity	NPC469544
0.6043	Remote Similarity	NPC81175
0.6043	Remote Similarity	NPC476451
0.604	Remote Similarity	NPC472443
0.6039	Remote Similarity	NPC32771
0.6037	Remote Similarity	NPC478075
0.6036	Remote Similarity	NPC469928
0.603	Remote Similarity	NPC158129
0.6028	Remote Similarity	NPC214368
0.602	Remote Similarity	NPC225857
0.6019	Remote Similarity	NPC469563
0.6018	Remote Similarity	NPC471080
0.6018	Remote Similarity	NPC478074
0.6018	Remote Similarity	NPC469592
0.6017	Remote Similarity	NPC469452
0.601	Remote Similarity	NPC39822
0.601	Remote Similarity	NPC469462
0.6009	Remote Similarity	NPC469727
0.6009	Remote Similarity	NPC128823
0.6009	Remote Similarity	NPC32200
0.6	Remote Similarity	NPC477397
0.6	Remote Similarity	NPC471294
0.6	Remote Similarity	NPC203972
0.6	Remote Similarity	NPC477185
0.5991	Remote Similarity	NPC314948
0.5991	Remote Similarity	NPC478049
0.5983	Remote Similarity	NPC6215
0.5983	Remote Similarity	NPC471891
0.5981	Remote Similarity	NPC127178
0.598	Remote Similarity	NPC314940
0.598	Remote Similarity	NPC473764
0.5972	Remote Similarity	NPC476098
0.5971	Remote Similarity	NPC313886
0.5971	Remote Similarity	NPC474258
0.5971	Remote Similarity	NPC314002
0.597	Remote Similarity	NPC475097
0.5967	Remote Similarity	NPC149379
0.5966	Remote Similarity	NPC329932
0.5962	Remote Similarity	NPC192315
0.596	Remote Similarity	NPC127362
0.596	Remote Similarity	NPC278887
0.5957	Remote Similarity	NPC151171
0.5957	Remote Similarity	NPC119569
0.5956	Remote Similarity	NPC222046
0.5952	Remote Similarity	NPC99666
0.5951	Remote Similarity	NPC472444
0.5951	Remote Similarity	NPC220765
0.5949	Remote Similarity	NPC291359
0.5948	Remote Similarity	NPC475720
0.5948	Remote Similarity	NPC474192
0.5946	Remote Similarity	NPC243162
0.5945	Remote Similarity	NPC475070
0.5942	Remote Similarity	NPC262725
0.5942	Remote Similarity	NPC171171
0.5939	Remote Similarity	NPC32028
0.5939	Remote Similarity	NPC132631
0.5939	Remote Similarity	NPC103687
0.5936	Remote Similarity	NPC330683
0.5936	Remote Similarity	NPC329567
0.5936	Remote Similarity	NPC475910
0.5935	Remote Similarity	NPC476167
0.5932	Remote Similarity	NPC469450
0.5931	Remote Similarity	NPC223242
0.5931	Remote Similarity	NPC166169
0.5928	Remote Similarity	NPC10730
0.5928	Remote Similarity	NPC315257
0.5928	Remote Similarity	NPC10875
0.5924	Remote Similarity	NPC474177
0.5922	Remote Similarity	NPC97584
0.5922	Remote Similarity	NPC204717
0.5921	Remote Similarity	NPC167908
0.5918	Remote Similarity	NPC322976
0.5918	Remote Similarity	NPC324203
0.5918	Remote Similarity	NPC309531
0.5918	Remote Similarity	NPC472102
0.5918	Remote Similarity	NPC63338
0.5915	Remote Similarity	NPC232130
0.5913	Remote Similarity	NPC471513
0.5911	Remote Similarity	NPC326575
0.5911	Remote Similarity	NPC477187
0.5909	Remote Similarity	NPC477160
0.5909	Remote Similarity	NPC470508
0.5907	Remote Similarity	NPC329793
0.5905	Remote Similarity	NPC92803
0.5904	Remote Similarity	NPC473804
0.5901	Remote Similarity	NPC94157
0.5896	Remote Similarity	NPC133366
0.5895	Remote Similarity	NPC19175
0.5894	Remote Similarity	NPC476575
0.5893	Remote Similarity	NPC470799
0.5893	Remote Similarity	NPC8022
0.5891	Remote Similarity	NPC472586
0.5889	Remote Similarity	NPC226662
0.5888	Remote Similarity	NPC315214
0.5888	Remote Similarity	NPC472117
0.5888	Remote Similarity	NPC47298
0.5888	Remote Similarity	NPC59028
0.5888	Remote Similarity	NPC92191
0.5887	Remote Similarity	NPC253580
0.5885	Remote Similarity	NPC473628
0.5885	Remote Similarity	NPC255110
0.5885	Remote Similarity	NPC46413
0.5885	Remote Similarity	NPC18890
0.5882	Remote Similarity	NPC72980
0.5882	Remote Similarity	NPC477155
0.5882	Remote Similarity	NPC88363
0.5882	Remote Similarity	NPC469451
0.5882	Remote Similarity	NPC99043
0.5882	Remote Similarity	NPC218594
0.588	Remote Similarity	NPC139373

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 NPC476250 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	173
0.1-0.2	597
0.2-0.3	999
0.3-0.4	1647
0.4-0.5	3781
0.5-0.6	1849
0.6-0.7	103
0.7-0.8	1
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
0.6902	Remote Similarity	NPD6283	Phase 2
0.6802	Remote Similarity	NPD4951	Discontinued
0.6798	Remote Similarity	NPD2177	Approved
0.6798	Remote Similarity	NPD2176	Approved
0.6798	Remote Similarity	NPD2175	Phase 3
0.6789	Remote Similarity	NPD5680	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD3329	Clinical (unspecified phase)
0.6613	Remote Similarity	NPD2789	Approved
0.6604	Remote Similarity	NPD5936	Approved
0.6604	Remote Similarity	NPD5939	Approved
0.6596	Remote Similarity	NPD5599	Discontinued
0.6498	Remote Similarity	NPD8109	Clinical (unspecified phase)
0.6495	Remote Similarity	NPD5078	Clinical (unspecified phase)
0.6493	Remote Similarity	NPD6290	Phase 2
0.6489	Remote Similarity	NPD1769	Discontinued
0.6461	Remote Similarity	NPD3864	Clinical (unspecified phase)
0.6449	Remote Similarity	NPD4502	Phase 2
0.6429	Remote Similarity	NPD6506	Clinical (unspecified phase)
0.6359	Remote Similarity	NPD1305	Clinical (unspecified phase)
0.635	Remote Similarity	NPD7883	Discontinued
0.6347	Remote Similarity	NPD7292	Approved
0.6345	Remote Similarity	NPD2381	Approved
0.6345	Remote Similarity	NPD2382	Approved
0.6345	Remote Similarity	NPD2380	Approved
0.6335	Remote Similarity	NPD3560	Approved
0.6335	Remote Similarity	NPD3556	Approved
0.6335	Remote Similarity	NPD3559	Clinical (unspecified phase)
0.6335	Remote Similarity	NPD3558	Approved
0.6335	Remote Similarity	NPD3557	Approved
0.6327	Remote Similarity	NPD6607	Clinical (unspecified phase)
0.6324	Remote Similarity	NPD7630	Phase 3
0.6324	Remote Similarity	NPD7629	Clinical (unspecified phase)
0.6324	Remote Similarity	NPD7628	Phase 3
0.6316	Remote Similarity	NPD5547	Clinical (unspecified phase)
0.6313	Remote Similarity	NPD6159	Phase 2
0.6296	Remote Similarity	NPD6220	Phase 3
0.6286	Remote Similarity	NPD995	Clinical (unspecified phase)
0.6283	Remote Similarity	NPD6060	Clinical (unspecified phase)
0.6281	Remote Similarity	NPD795	Clinical (unspecified phase)
0.6269	Remote Similarity	NPD5596	Phase 2
0.6269	Remote Similarity	NPD863	Approved
0.6269	Remote Similarity	NPD5522	Clinical (unspecified phase)
0.6269	Remote Similarity	NPD861	Approved
0.6269	Remote Similarity	NPD862	Approved
0.6262	Remote Similarity	NPD4596	Phase 1
0.6257	Remote Similarity	NPD1405	Approved
0.6256	Remote Similarity	NPD6340	Approved
0.6256	Remote Similarity	NPD6339	Approved
0.625	Remote Similarity	NPD5645	Phase 3
0.6244	Remote Similarity	NPD4036	Approved
0.6244	Remote Similarity	NPD4033	Approved
0.6244	Remote Similarity	NPD2843	Phase 2
0.6244	Remote Similarity	NPD4038	Approved
0.6244	Remote Similarity	NPD32	Approved
0.6244	Remote Similarity	NPD4122	Approved
0.6244	Remote Similarity	NPD2845	Phase 2
0.6244	Remote Similarity	NPD4037	Approved
0.6244	Remote Similarity	NPD4035	Approved
0.6244	Remote Similarity	NPD31	Approved
0.6244	Remote Similarity	NPD4039	Approved
0.6244	Remote Similarity	NPD4034	Approved
0.6216	Remote Similarity	NPD5595	Clinical (unspecified phase)
0.6199	Remote Similarity	NPD7293	Approved
0.6196	Remote Similarity	NPD6301	Phase 2
0.6193	Remote Similarity	NPD4083	Discontinued
0.6161	Remote Similarity	NPD5999	Phase 2
0.6157	Remote Similarity	NPD4022	Approved
0.6157	Remote Similarity	NPD3472	Approved
0.6154	Remote Similarity	NPD5575	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD3940	Clinical (unspecified phase)
0.615	Remote Similarity	NPD5670	Approved
0.6139	Remote Similarity	NPD7149	Clinical (unspecified phase)
0.6131	Remote Similarity	NPD5602	Clinical (unspecified phase)
0.6119	Remote Similarity	NPD4492	Approved
0.6119	Remote Similarity	NPD4494	Approved
0.6114	Remote Similarity	NPD6737	Phase 2
0.6114	Remote Similarity	NPD6738	Phase 2
0.6111	Remote Similarity	NPD2216	Approved
0.6111	Remote Similarity	NPD2215	Approved
0.6105	Remote Similarity	NPD5267	Discontinued
0.6103	Remote Similarity	NPD4511	Phase 1
0.6101	Remote Similarity	NPD3372	Discontinued
0.6099	Remote Similarity	NPD3552	Approved
0.6099	Remote Similarity	NPD3555	Approved
0.6099	Remote Similarity	NPD3553	Approved
0.6099	Remote Similarity	NPD3554	Approved
0.6098	Remote Similarity	NPD5256	Discontinued
0.6094	Remote Similarity	NPD980	Clinical (unspecified phase)
0.6093	Remote Similarity	NPD4456	Clinical (unspecified phase)
0.6091	Remote Similarity	NPD6379	Discontinued
0.6083	Remote Similarity	NPD4082	Approved
0.6082	Remote Similarity	NPD6524	Clinical (unspecified phase)
0.6068	Remote Similarity	NPD2383	Phase 1
0.605	Remote Similarity	NPD5938	Phase 3
0.6048	Remote Similarity	NPD6871	Clinical (unspecified phase)
0.6032	Remote Similarity	NPD5881	Clinical (unspecified phase)
0.6031	Remote Similarity	NPD4514	Approved
0.6029	Remote Similarity	NPD5937	Approved
0.601	Remote Similarity	NPD2468	Approved
0.601	Remote Similarity	NPD2469	Approved
0.6009	Remote Similarity	NPD7300	Phase 3
0.6009	Remote Similarity	NPD7302	Phase 3
0.6	Remote Similarity	NPD1953	Discontinued
0.6	Remote Similarity	NPD4725	Approved
0.6	Remote Similarity	NPD4721	Approved
0.6	Remote Similarity	NPD4726	Approved
0.6	Remote Similarity	NPD7262	Phase 1
0.6	Remote Similarity	NPD9695	Approved
0.6	Remote Similarity	NPD6199	Discontinued
0.5991	Remote Similarity	NPD4604	Approved
0.5991	Remote Similarity	NPD4605	Approved
0.599	Remote Similarity	NPD4121	Phase 3
0.599	Remote Similarity	NPD4120	Approved
0.5973	Remote Similarity	NPD3330	Phase 1
0.5973	Remote Similarity	NPD7726	Phase 1
0.5973	Remote Similarity	NPD3888	Discontinued
0.5971	Remote Similarity	NPD6557	Phase 2
0.597	Remote Similarity	NPD6316	Clinical (unspecified phase)
0.5965	Remote Similarity	NPD7586	Clinical (unspecified phase)
0.5963	Remote Similarity	NPD7263	Phase 2
0.5962	Remote Similarity	NPD7889	Clinical (unspecified phase)
0.5961	Remote Similarity	NPD7479	Phase 2
0.5959	Remote Similarity	NPD5741	Approved
0.5959	Remote Similarity	NPD5742	Approved
0.5959	Remote Similarity	NPD5743	Approved
0.5957	Remote Similarity	NPD8131	Suspended
0.5956	Remote Similarity	NPD817	Approved
0.5956	Remote Similarity	NPD823	Approved
0.5955	Remote Similarity	NPD3893	Discontinued
0.5955	Remote Similarity	NPD602	Approved
0.5955	Remote Similarity	NPD599	Approved
0.5946	Remote Similarity	NPD4455	Discontinued
0.5938	Remote Similarity	NPD950	Clinical (unspecified phase)
0.5936	Remote Similarity	NPD2907	Approved
0.5936	Remote Similarity	NPD2906	Approved
0.5935	Remote Similarity	NPD4118	Clinical (unspecified phase)
0.5929	Remote Similarity	NPD6633	Phase 2
0.5929	Remote Similarity	NPD6634	Clinical (unspecified phase)
0.5926	Remote Similarity	NPD5669	Clinical (unspecified phase)
0.5924	Remote Similarity	NPD4410	Clinical (unspecified phase)
0.5924	Remote Similarity	NPD4411	Phase 1
0.5922	Remote Similarity	NPD5083	Clinical (unspecified phase)
0.5922	Remote Similarity	NPD5895	Clinical (unspecified phase)
0.5918	Remote Similarity	NPD9398	Clinical (unspecified phase)
0.5916	Remote Similarity	NPD5546	Clinical (unspecified phase)
0.5913	Remote Similarity	NPD3120	Approved
0.5913	Remote Similarity	NPD3119	Phase 1
0.5912	Remote Similarity	NPD864	Approved
0.5912	Remote Similarity	NPD865	Approved
0.5909	Remote Similarity	NPD6503	Clinical (unspecified phase)
0.5909	Remote Similarity	NPD4437	Phase 3
0.5909	Remote Similarity	NPD2562	Approved
0.5909	Remote Similarity	NPD2561	Approved
0.5907	Remote Similarity	NPD6612	Phase 2
0.5905	Remote Similarity	NPD6656	Clinical (unspecified phase)
0.5905	Remote Similarity	NPD5042	Phase 1
0.5905	Remote Similarity	NPD5641	Discontinued
0.5899	Remote Similarity	NPD4103	Phase 2
0.5899	Remote Similarity	NPD4104	Clinical (unspecified phase)
0.5897	Remote Similarity	NPD4671	Clinical (unspecified phase)
0.5897	Remote Similarity	NPD4670	Clinical (unspecified phase)
0.5897	Remote Similarity	NPD4669	Clinical (unspecified phase)
0.5896	Remote Similarity	NPD4771	Phase 2
0.5895	Remote Similarity	NPD4890	Phase 2
0.5894	Remote Similarity	NPD2762	Phase 2
0.5891	Remote Similarity	NPD5065	Approved
0.5891	Remote Similarity	NPD9690	Approved
0.589	Remote Similarity	NPD7222	Phase 2
0.5888	Remote Similarity	NPD4871	Phase 2
0.5888	Remote Similarity	NPD1685	Approved
0.5888	Remote Similarity	NPD2995	Approved
0.5888	Remote Similarity	NPD1684	Approved
0.5882	Remote Similarity	NPD1908	Phase 2
0.5879	Remote Similarity	NPD1595	Approved
0.5879	Remote Similarity	NPD1594	Phase 3
0.5879	Remote Similarity	NPD6767	Clinical (unspecified phase)
0.5876	Remote Similarity	NPD4659	Approved
0.5874	Remote Similarity	NPD1381	Clinical (unspecified phase)
0.5874	Remote Similarity	NPD3253	Clinical (unspecified phase)
0.5872	Remote Similarity	NPD1294	Discontinued
0.5871	Remote Similarity	NPD3975	Discontinued
0.5871	Remote Similarity	NPD3883	Clinical (unspecified phase)
0.587	Remote Similarity	NPD2568	Approved
0.5866	Remote Similarity	NPD858	Approved
0.5866	Remote Similarity	NPD859	Approved
0.5862	Remote Similarity	NPD4354	Approved
0.586	Remote Similarity	NPD3068	Approved
0.586	Remote Similarity	NPD3605	Approved
0.586	Remote Similarity	NPD6606	Clinical (unspecified phase)
0.586	Remote Similarity	NPD5608	Approved
0.586	Remote Similarity	NPD6874	Approved
0.586	Remote Similarity	NPD5609	Approved
0.5859	Remote Similarity	NPD3783	Clinical (unspecified phase)
0.5856	Remote Similarity	NPD4493	Discontinued
0.5855	Remote Similarity	NPD6476	Clinical (unspecified phase)
0.5855	Remote Similarity	NPD6158	Phase 2
0.5852	Remote Similarity	NPD5350	Clinical (unspecified phase)
0.5852	Remote Similarity	NPD5351	Clinical (unspecified phase)
0.585	Remote Similarity	NPD3983	Phase 3
0.585	Remote Similarity	NPD3984	Clinical (unspecified phase)

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