NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	264.05
Volume:	258.406
LogP:	2.529
LogD:	2.113
LogS:	-4.811
# Rotatable Bonds:	0
TPSA:	72.19
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.524
Synthetic Accessibility Score:	2.211
Fsp3:	0.0
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.835
MDCK Permeability:	1.9398104996071197e-05
Pgp-inhibitor:	0.006
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.008
30% Bioavailability (F30%):	0.823

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.758
Plasma Protein Binding (PPB):	96.11056518554688%
Volume Distribution (VD):	0.409
Pgp-substrate:	1.9480993747711182%

ADMET: Metabolism

CYP1A2-inhibitor:	0.952
CYP1A2-substrate:	0.587
CYP2C19-inhibitor:	0.171
CYP2C19-substrate:	0.102
CYP2C9-inhibitor:	0.719
CYP2C9-substrate:	0.533
CYP2D6-inhibitor:	0.195
CYP2D6-substrate:	0.305
CYP3A4-inhibitor:	0.621
CYP3A4-substrate:	0.695

ADMET: Excretion

Clearance (CL):	1.298
Half-life (T1/2):	0.411

ADMET: Toxicity

hERG Blockers:	0.032
Human Hepatotoxicity (H-HT):	0.148
Drug-inuced Liver Injury (DILI):	0.935
AMES Toxicity:	0.943
Rat Oral Acute Toxicity:	0.113
Maximum Recommended Daily Dose:	0.239
Skin Sensitization:	0.129
Carcinogencity:	0.933
Eye Corrosion:	0.004
Eye Irritation:	0.885
Respiratory Toxicity:	0.104

Download Data

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

Natural Product: NPC150308

Natural Product ID:	NPC150308
*Common Name:**	Phaitanthrin C
IUPAC Name:	7-hydroxyindolo[2,1-b]quinazoline-6,12-dione
Synonyms:	7-Hydroxytryptanthrin
Standard InCHIKey:	WOQXYBJCORZEEE-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C15H8N2O3/c18-11-7-3-6-10-12(11)13(19)14-16-9-5-2-1-4-8(9)15(20)17(10)14/h1-7,18H
SMILES:	c1ccc2c(c1)c(=O)n1-c3cccc(c3C(=O)c1n2)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL452806
PubChem CID:	24970644
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0004788] Diazanaphthalenes [CHEMONTID:0004789] Benzodiazines [CHEMONTID:0000485] Quinazolines [CHEMONTID:0002087] Indoloquinazolines

*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
NPO4147	Phaius mishmensis	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18507473]
NPO4147	Phaius mishmensis	Species	Orchidaceae	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	3

Activity Type	# Activity
Cell Line	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT83	Cell Line	MCF7	Homo sapiens	IC50	>	50000.0	nM	PMID[507647]
NPT397	Cell Line	NCI-H460	Homo sapiens	IC50	>	50000.0	nM	PMID[507647]
NPT395	Cell Line	SF-268	Homo sapiens	IC50	>	50000.0	nM	PMID[507647]

☑ 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 NPC150308 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	771
0.1-0.2	6032
0.2-0.3	11399
0.3-0.4	11342
0.4-0.5	9654
0.5-0.6	2584
0.6-0.7	763
0.7-0.8	136
0.8-0.85	15
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8256	Intermediate Similarity	NPC204867
0.8239	Intermediate Similarity	NPC475594
0.8192	Intermediate Similarity	NPC475607
0.8146	Intermediate Similarity	NPC474081
0.8101	Intermediate Similarity	NPC475761
0.8101	Intermediate Similarity	NPC474041
0.8087	Intermediate Similarity	NPC473815
0.7946	Intermediate Similarity	NPC18890
0.7879	Intermediate Similarity	NPC207554
0.7861	Intermediate Similarity	NPC92803
0.7857	Intermediate Similarity	NPC475685
0.7784	Intermediate Similarity	NPC88970
0.7778	Intermediate Similarity	NPC144691
0.776	Intermediate Similarity	NPC298320
0.7697	Intermediate Similarity	NPC471130
0.7488	Intermediate Similarity	NPC220851
0.7414	Intermediate Similarity	NPC237649
0.7414	Intermediate Similarity	NPC300596
0.7371	Intermediate Similarity	NPC198401
0.7358	Intermediate Similarity	NPC206109
0.7358	Intermediate Similarity	NPC114039
0.7345	Intermediate Similarity	NPC295021
0.7337	Intermediate Similarity	NPC295548
0.7308	Intermediate Similarity	NPC299582
0.7264	Intermediate Similarity	NPC225400
0.7245	Intermediate Similarity	NPC470787
0.7245	Intermediate Similarity	NPC472540
0.7245	Intermediate Similarity	NPC472539
0.7228	Intermediate Similarity	NPC471155
0.7228	Intermediate Similarity	NPC472538
0.7228	Intermediate Similarity	NPC470786
0.7208	Intermediate Similarity	NPC472542
0.7208	Intermediate Similarity	NPC472541
0.7192	Intermediate Similarity	NPC270241
0.7143	Intermediate Similarity	NPC198160
0.7128	Intermediate Similarity	NPC1820
0.7118	Intermediate Similarity	NPC300299
0.7114	Intermediate Similarity	NPC15987
0.7105	Intermediate Similarity	NPC39822
0.7104	Intermediate Similarity	NPC199737
0.7077	Intermediate Similarity	NPC471195
0.7077	Intermediate Similarity	NPC471196
0.7074	Intermediate Similarity	NPC470548
0.7071	Intermediate Similarity	NPC170333
0.7059	Intermediate Similarity	NPC16249
0.703	Intermediate Similarity	NPC288759
0.7006	Intermediate Similarity	NPC324445
0.7006	Intermediate Similarity	NPC146370
0.6991	Remote Similarity	NPC471762
0.6971	Remote Similarity	NPC116178
0.6957	Remote Similarity	NPC27904
0.6957	Remote Similarity	NPC93653
0.6942	Remote Similarity	NPC86834
0.6942	Remote Similarity	NPC210828
0.6941	Remote Similarity	NPC207428
0.6938	Remote Similarity	NPC321166
0.6938	Remote Similarity	NPC217903
0.6912	Remote Similarity	NPC66777
0.6911	Remote Similarity	NPC9475
0.6897	Remote Similarity	NPC83214
0.6878	Remote Similarity	NPC474814
0.6878	Remote Similarity	NPC313112
0.6878	Remote Similarity	NPC133156
0.6878	Remote Similarity	NPC112336
0.6878	Remote Similarity	NPC301292
0.6866	Remote Similarity	NPC471199
0.6842	Remote Similarity	NPC220241
0.6842	Remote Similarity	NPC23294
0.6842	Remote Similarity	NPC295479
0.6832	Remote Similarity	NPC234933
0.6829	Remote Similarity	NPC200836
0.6816	Remote Similarity	NPC303214
0.6808	Remote Similarity	NPC248601
0.6802	Remote Similarity	NPC206186
0.6798	Remote Similarity	NPC106118
0.6798	Remote Similarity	NPC323798
0.6794	Remote Similarity	NPC303951
0.6791	Remote Similarity	NPC138293
0.6791	Remote Similarity	NPC113056
0.6789	Remote Similarity	NPC157931
0.6784	Remote Similarity	NPC203628
0.678	Remote Similarity	NPC301702
0.6761	Remote Similarity	NPC204156
0.6753	Remote Similarity	NPC166169
0.6753	Remote Similarity	NPC5167
0.6748	Remote Similarity	NPC41216
0.6748	Remote Similarity	NPC134848
0.6738	Remote Similarity	NPC476231
0.6737	Remote Similarity	NPC471778
0.6734	Remote Similarity	NPC45389
0.6731	Remote Similarity	NPC212123
0.6731	Remote Similarity	NPC478075
0.6723	Remote Similarity	NPC2823
0.6723	Remote Similarity	NPC471574
0.6718	Remote Similarity	NPC270301
0.6716	Remote Similarity	NPC241263
0.6714	Remote Similarity	NPC3207
0.6713	Remote Similarity	NPC329830
0.6704	Remote Similarity	NPC297322
0.6686	Remote Similarity	NPC316746
0.6685	Remote Similarity	NPC476444
0.6685	Remote Similarity	NPC471132
0.6682	Remote Similarity	NPC244425
0.6682	Remote Similarity	NPC15384
0.6682	Remote Similarity	NPC220337
0.6667	Remote Similarity	NPC264400
0.6651	Remote Similarity	NPC305542
0.6651	Remote Similarity	NPC182853
0.6651	Remote Similarity	NPC270918
0.6651	Remote Similarity	NPC247803
0.665	Remote Similarity	NPC232600
0.6649	Remote Similarity	NPC475983
0.6648	Remote Similarity	NPC122553
0.6648	Remote Similarity	NPC166667
0.6636	Remote Similarity	NPC62995
0.6635	Remote Similarity	NPC163829
0.6631	Remote Similarity	NPC154478
0.6628	Remote Similarity	NPC226662
0.6622	Remote Similarity	NPC119006
0.6621	Remote Similarity	NPC122886
0.662	Remote Similarity	NPC30749
0.6619	Remote Similarity	NPC285192
0.6615	Remote Similarity	NPC355
0.6614	Remote Similarity	NPC189116
0.6613	Remote Similarity	NPC84317
0.6611	Remote Similarity	NPC136002
0.6605	Remote Similarity	NPC471197
0.6604	Remote Similarity	NPC146418
0.6604	Remote Similarity	NPC218303
0.6601	Remote Similarity	NPC276517
0.66	Remote Similarity	NPC221873
0.6598	Remote Similarity	NPC471743
0.659	Remote Similarity	NPC150239
0.6587	Remote Similarity	NPC53144
0.6585	Remote Similarity	NPC306376
0.6582	Remote Similarity	NPC85613
0.658	Remote Similarity	NPC474409
0.6578	Remote Similarity	NPC469428
0.6578	Remote Similarity	NPC473187
0.6575	Remote Similarity	NPC314633
0.6574	Remote Similarity	NPC471198
0.6574	Remote Similarity	NPC134702
0.6573	Remote Similarity	NPC47986
0.6573	Remote Similarity	NPC12344
0.657	Remote Similarity	NPC471944
0.6567	Remote Similarity	NPC5630
0.6567	Remote Similarity	NPC174629
0.6566	Remote Similarity	NPC302235
0.6561	Remote Similarity	NPC191863
0.6561	Remote Similarity	NPC289776
0.6561	Remote Similarity	NPC133470
0.6558	Remote Similarity	NPC322064
0.6557	Remote Similarity	NPC474366
0.6546	Remote Similarity	NPC303225
0.6545	Remote Similarity	NPC182131
0.6541	Remote Similarity	NPC184161
0.654	Remote Similarity	NPC207873
0.654	Remote Similarity	NPC39679
0.654	Remote Similarity	NPC100573
0.6538	Remote Similarity	NPC295898
0.6536	Remote Similarity	NPC43477
0.6533	Remote Similarity	NPC241025
0.6531	Remote Similarity	NPC126515
0.6531	Remote Similarity	NPC472331
0.6531	Remote Similarity	NPC274002
0.6528	Remote Similarity	NPC469671
0.6528	Remote Similarity	NPC318183
0.6528	Remote Similarity	NPC126676
0.6514	Remote Similarity	NPC128115
0.6514	Remote Similarity	NPC174760
0.6512	Remote Similarity	NPC148391
0.6512	Remote Similarity	NPC2905
0.6512	Remote Similarity	NPC176113
0.6505	Remote Similarity	NPC100863
0.6505	Remote Similarity	NPC472284
0.6504	Remote Similarity	NPC35042
0.6502	Remote Similarity	NPC204970
0.6497	Remote Similarity	NPC283810
0.6495	Remote Similarity	NPC177261
0.6493	Remote Similarity	NPC183777
0.6486	Remote Similarity	NPC257851
0.6485	Remote Similarity	NPC474059
0.6484	Remote Similarity	NPC118189
0.6477	Remote Similarity	NPC253476
0.6476	Remote Similarity	NPC14339
0.6474	Remote Similarity	NPC209389
0.6473	Remote Similarity	NPC317727
0.6471	Remote Similarity	NPC97746
0.6471	Remote Similarity	NPC254698
0.6468	Remote Similarity	NPC48317
0.6465	Remote Similarity	NPC28368
0.6465	Remote Similarity	NPC114468
0.6464	Remote Similarity	NPC308197
0.6462	Remote Similarity	NPC90185
0.6461	Remote Similarity	NPC242159
0.6461	Remote Similarity	NPC313694
0.6461	Remote Similarity	NPC316574
0.6457	Remote Similarity	NPC194740
0.6456	Remote Similarity	NPC78767
0.6456	Remote Similarity	NPC473814

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 NPC150308 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	431
0.1-0.2	688
0.2-0.3	873
0.3-0.4	2118
0.4-0.5	2507
0.5-0.6	1879
0.6-0.7	618
0.7-0.8	36
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
0.7725	Intermediate Similarity	NPD5937	Approved
0.7296	Intermediate Similarity	NPD5515	Phase 2
0.7246	Intermediate Similarity	NPD3949	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD1165	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD3229	Phase 2
0.715	Intermediate Similarity	NPD4515	Suspended
0.7143	Intermediate Similarity	NPD1920	Approved
0.7143	Intermediate Similarity	NPD1919	Approved
0.7105	Intermediate Similarity	NPD5445	Approved
0.7083	Intermediate Similarity	NPD5923	Phase 1
0.7053	Intermediate Similarity	NPD3239	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD1168	Approved
0.7	Intermediate Similarity	NPD3793	Phase 3
0.6995	Remote Similarity	NPD3802	Phase 3
0.697	Remote Similarity	NPD4539	Phase 1
0.6919	Remote Similarity	NPD2791	Discontinued
0.6891	Remote Similarity	NPD5637	Discontinued
0.689	Remote Similarity	NPD7225	Discontinued
0.6881	Remote Similarity	NPD5882	Clinical (unspecified phase)
0.6872	Remote Similarity	NPD6557	Phase 2
0.6866	Remote Similarity	NPD5591	Approved
0.6854	Remote Similarity	NPD6017	Discontinued
0.6827	Remote Similarity	NPD5593	Approved
0.6827	Remote Similarity	NPD5594	Approved
0.6825	Remote Similarity	NPD1161	Approved
0.6798	Remote Similarity	NPD1196	Approved
0.6796	Remote Similarity	NPD4465	Phase 2
0.6796	Remote Similarity	NPD4467	Phase 2
0.6793	Remote Similarity	NPD2469	Approved
0.6793	Remote Similarity	NPD2468	Approved
0.6784	Remote Similarity	NPD5042	Phase 1
0.6782	Remote Similarity	NPD4423	Clinical (unspecified phase)
0.678	Remote Similarity	NPD9277	Approved
0.678	Remote Similarity	NPD75	Approved
0.678	Remote Similarity	NPD7071	Clinical (unspecified phase)
0.6779	Remote Similarity	NPD2916	Discontinued
0.6778	Remote Similarity	NPD1543	Discontinued
0.6771	Remote Similarity	NPD1544	Phase 1
0.6771	Remote Similarity	NPD2361	Approved
0.6763	Remote Similarity	NPD7174	Clinical (unspecified phase)
0.6761	Remote Similarity	NPD3391	Approved
0.6742	Remote Similarity	NPD1195	Approved
0.6742	Remote Similarity	NPD4430	Phase 2
0.674	Remote Similarity	NPD4939	Clinical (unspecified phase)
0.6736	Remote Similarity	NPD1170	Approved
0.6723	Remote Similarity	NPD9276	Approved
0.6723	Remote Similarity	NPD9278	Suspended
0.6723	Remote Similarity	NPD9274	Approved
0.6723	Remote Similarity	NPD9275	Approved
0.6719	Remote Similarity	NPD7449	Clinical (unspecified phase)
0.6719	Remote Similarity	NPD2359	Approved
0.6702	Remote Similarity	NPD1913	Phase 1
0.67	Remote Similarity	NPD4979	Clinical (unspecified phase)
0.6699	Remote Similarity	NPD956	Clinical (unspecified phase)
0.6683	Remote Similarity	NPD6608	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6480	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5197	Approved
0.6667	Remote Similarity	NPD5194	Approved
0.6667	Remote Similarity	NPD5856	Discontinued
0.6667	Remote Similarity	NPD5196	Approved
0.665	Remote Similarity	NPD5552	Discontinued
0.6649	Remote Similarity	NPD1839	Phase 1
0.6648	Remote Similarity	NPD1625	Approved
0.6648	Remote Similarity	NPD4942	Approved
0.6636	Remote Similarity	NPD4845	Discontinued
0.6635	Remote Similarity	NPD6138	Clinical (unspecified phase)
0.6635	Remote Similarity	NPD3298	Approved
0.6634	Remote Similarity	NPD6874	Approved
0.662	Remote Similarity	NPD4312	Approved
0.6614	Remote Similarity	NPD955	Approved
0.6613	Remote Similarity	NPD951	Approved
0.6609	Remote Similarity	NPD1541	Approved
0.6608	Remote Similarity	NPD6790	Phase 1
0.6604	Remote Similarity	NPD683	Approved
0.6604	Remote Similarity	NPD6567	Clinical (unspecified phase)
0.6592	Remote Similarity	NPD1189	Approved
0.6591	Remote Similarity	NPD7186	Phase 3
0.6577	Remote Similarity	NPD6199	Discontinued
0.6573	Remote Similarity	NPD7301	Phase 3
0.6571	Remote Similarity	NPD2758	Phase 1
0.657	Remote Similarity	NPD7566	Clinical (unspecified phase)
0.6566	Remote Similarity	NPD4412	Phase 2
0.6562	Remote Similarity	NPD5183	Approved
0.6562	Remote Similarity	NPD5186	Approved
0.6557	Remote Similarity	NPD4888	Discontinued
0.6557	Remote Similarity	NPD979	Approved
0.6553	Remote Similarity	NPD3297	Approved
0.6545	Remote Similarity	NPD5823	Approved
0.6544	Remote Similarity	NPD5496	Approved
0.6538	Remote Similarity	NPD1524	Phase 1
0.6537	Remote Similarity	NPD5195	Discontinued
0.6528	Remote Similarity	NPD3776	Discontinued
0.6524	Remote Similarity	NPD6260	Discontinued
0.6518	Remote Similarity	NPD7031	Phase 1
0.6518	Remote Similarity	NPD5151	Clinical (unspecified phase)
0.6515	Remote Similarity	NPD3253	Clinical (unspecified phase)
0.6514	Remote Similarity	NPD3783	Clinical (unspecified phase)
0.6512	Remote Similarity	NPD4562	Clinical (unspecified phase)
0.6491	Remote Similarity	NPD7560	Approved
0.6489	Remote Similarity	NPD4373	Phase 2
0.6485	Remote Similarity	NPD7617	Discontinued
0.6481	Remote Similarity	NPD6744	Clinical (unspecified phase)
0.6479	Remote Similarity	NPD5860	Discontinued
0.6478	Remote Similarity	NPD4946	Phase 2
0.6473	Remote Similarity	NPD5609	Approved
0.6473	Remote Similarity	NPD5608	Approved
0.6471	Remote Similarity	NPD5610	Approved
0.6461	Remote Similarity	NPD9279	Approved
0.6453	Remote Similarity	NPD1593	Approved
0.6448	Remote Similarity	NPD3141	Discontinued
0.6436	Remote Similarity	NPD2792	Approved
0.6436	Remote Similarity	NPD7855	Clinical (unspecified phase)
0.6436	Remote Similarity	NPD2366	Approved
0.6435	Remote Similarity	NPD5417	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD4952	Phase 3
0.6425	Remote Similarity	NPD1626	Approved
0.6421	Remote Similarity	NPD2506	Approved
0.6419	Remote Similarity	NPD4561	Discontinued
0.6404	Remote Similarity	NPD5928	Phase 1
0.6398	Remote Similarity	NPD3277	Phase 3
0.6398	Remote Similarity	NPD1294	Discontinued
0.6396	Remote Similarity	NPD7545	Clinical (unspecified phase)
0.6396	Remote Similarity	NPD3792	Approved
0.6396	Remote Similarity	NPD6020	Phase 2
0.6396	Remote Similarity	NPD3755	Clinical (unspecified phase)
0.6393	Remote Similarity	NPD2899	Discontinued
0.6392	Remote Similarity	NPD3376	Clinical (unspecified phase)
0.6386	Remote Similarity	NPD4988	Discontinued
0.6381	Remote Similarity	NPD6795	Clinical (unspecified phase)
0.6381	Remote Similarity	NPD3773	Approved
0.6381	Remote Similarity	NPD3775	Approved
0.6381	Remote Similarity	NPD3774	Approved
0.6378	Remote Similarity	NPD4161	Discontinued
0.6377	Remote Similarity	NPD6161	Approved
0.6377	Remote Similarity	NPD6162	Approved
0.6376	Remote Similarity	NPD6719	Approved
0.6373	Remote Similarity	NPD2327	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD3782	Discontinued
0.6359	Remote Similarity	NPD6884	Clinical (unspecified phase)
0.6356	Remote Similarity	NPD4981	Phase 2
0.6355	Remote Similarity	NPD8025	Phase 2
0.6355	Remote Similarity	NPD5620	Clinical (unspecified phase)
0.6354	Remote Similarity	NPD9477	Approved
0.6351	Remote Similarity	NPD6478	Clinical (unspecified phase)
0.6349	Remote Similarity	NPD6855	Clinical (unspecified phase)
0.6346	Remote Similarity	NPD4668	Phase 2
0.6345	Remote Similarity	NPD3004	Clinical (unspecified phase)
0.6345	Remote Similarity	NPD8022	Clinical (unspecified phase)
0.6345	Remote Similarity	NPD5603	Clinical (unspecified phase)
0.6344	Remote Similarity	NPD2737	Clinical (unspecified phase)
0.6343	Remote Similarity	NPD7178	Clinical (unspecified phase)
0.634	Remote Similarity	NPD2821	Approved
0.6339	Remote Similarity	NPD3259	Approved
0.6338	Remote Similarity	NPD7043	Discontinued
0.6335	Remote Similarity	NPD4311	Approved
0.6333	Remote Similarity	NPD6321	Discontinued
0.6332	Remote Similarity	NPD4330	Approved
0.6332	Remote Similarity	NPD4329	Approved
0.633	Remote Similarity	NPD2433	Clinical (unspecified phase)
0.6328	Remote Similarity	NPD1594	Phase 3
0.6328	Remote Similarity	NPD1527	Phase 2
0.6328	Remote Similarity	NPD1595	Approved
0.6327	Remote Similarity	NPD3441	Approved
0.6327	Remote Similarity	NPD1505	Phase 2
0.6327	Remote Similarity	NPD3442	Approved
0.6326	Remote Similarity	NPD648	Clinical (unspecified phase)
0.6324	Remote Similarity	NPD4258	Approved
0.6324	Remote Similarity	NPD4259	Approved
0.6319	Remote Similarity	NPD2365	Approved
0.6318	Remote Similarity	NPD721	Approved
0.6316	Remote Similarity	NPD1861	Discovery
0.631	Remote Similarity	NPD1230	Approved
0.6305	Remote Similarity	NPD4948	Discontinued
0.6298	Remote Similarity	NPD1842	Approved
0.6296	Remote Similarity	NPD4493	Discontinued
0.6294	Remote Similarity	NPD7324	Discontinued
0.629	Remote Similarity	NPD5433	Clinical (unspecified phase)
0.6286	Remote Similarity	NPD7255	Clinical (unspecified phase)
0.6286	Remote Similarity	NPD2339	Phase 3
0.6284	Remote Similarity	NPD7559	Phase 2
0.6284	Remote Similarity	NPD2820	Phase 3
0.6283	Remote Similarity	NPD2427	Approved
0.6278	Remote Similarity	NPD6636	Phase 3
0.6274	Remote Similarity	NPD5513	Phase 2
0.6274	Remote Similarity	NPD7064	Clinical (unspecified phase)
0.6271	Remote Similarity	NPD3986	Discontinued
0.6269	Remote Similarity	NPD6533	Clinical (unspecified phase)
0.6263	Remote Similarity	NPD2672	Discontinued
0.6262	Remote Similarity	NPD7570	Approved
0.6262	Remote Similarity	NPD7569	Approved
0.6261	Remote Similarity	NPD4923	Phase 1
0.6261	Remote Similarity	NPD6252	Clinical (unspecified phase)
0.6261	Remote Similarity	NPD5532	Phase 2
0.6256	Remote Similarity	NPD5025	Approved
0.6256	Remote Similarity	NPD3286	Discontinued
0.6256	Remote Similarity	NPD6457	Approved
0.6256	Remote Similarity	NPD2037	Approved
0.6256	Remote Similarity	NPD6962	Phase 2
0.6256	Remote Similarity	NPD2404	Discontinued
0.6256	Remote Similarity	NPD7439	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