NPASS Compound

Structure

NPC471943 OpenBabel07101719512D 22 26 0 0 0 0 0 0 0 0999 V2000 4.6722 0.5181 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8966 0.7226 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6722 1.5181 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6887 -0.2556 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8061 0.0181 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1535 1.3917 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8061 2.0181 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7377 -0.5646 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5823 -0.7045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9401 0.5181 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2024 1.0827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9890 0.2091 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9401 1.5181 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9945 0.1045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5878 -0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4013 1.0181 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4067 0.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3364 1.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9890 1.8271 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 0.1810 -1.7226 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.2319 2.5772 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 3 2 0 0 0 0 1 5 1 0 0 0 0 2 4 2 0 0 0 0 2 6 1 0 0 0 0 3 7 1 0 0 0 0 4 8 1 0 0 0 0 5 10 2 0 0 0 0 6 11 2 0 0 0 0 7 13 2 0 0 0 0 8 14 2 0 0 0 0 9 12 2 0 0 0 0 9 15 1 0 0 0 0 10 12 1 0 0 0 0 10 13 1 0 0 0 0 11 14 1 0 0 0 0 11 18 1 0 0 0 0 12 16 1 0 0 0 0 13 19 1 0 0 0 0 14 20 1 0 0 0 0 15 20 1 0 0 0 0 15 21 2 0 0 0 0 16 17 2 0 0 0 0 16 19 1 0 0 0 0 17 18 1 0 0 0 0 17 20 1 0 0 0 0 18 22 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	286.07
Volume:	290.311
LogP:	3.224
LogD:	3.12
LogS:	-5.961
# Rotatable Bonds:	0
TPSA:	54.86
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	5
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.476
Synthetic Accessibility Score:	2.456
Fsp3:	0.0
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-5.009
MDCK Permeability:	1.2747355867759325e-05
Pgp-inhibitor:	0.26
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.013
30% Bioavailability (F30%):	0.981

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.806
Plasma Protein Binding (PPB):	94.5922622680664%
Volume Distribution (VD):	0.47
Pgp-substrate:	1.8087214231491089%

ADMET: Metabolism

CYP1A2-inhibitor:	0.972
CYP1A2-substrate:	0.847
CYP2C19-inhibitor:	0.57
CYP2C19-substrate:	0.192
CYP2C9-inhibitor:	0.855
CYP2C9-substrate:	0.559
CYP2D6-inhibitor:	0.405
CYP2D6-substrate:	0.196
CYP3A4-inhibitor:	0.786
CYP3A4-substrate:	0.862

ADMET: Excretion

Clearance (CL):	3.218
Half-life (T1/2):	0.386

ADMET: Toxicity

hERG Blockers:	0.033
Human Hepatotoxicity (H-HT):	0.555
Drug-inuced Liver Injury (DILI):	0.927
AMES Toxicity:	0.907
Rat Oral Acute Toxicity:	0.169
Maximum Recommended Daily Dose:	0.97
Skin Sensitization:	0.159
Carcinogencity:	0.952
Eye Corrosion:	0.003
Eye Irritation:	0.266
Respiratory Toxicity:	0.274

Download Data

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

Natural Product: NPC471943

Natural Product ID:	NPC471943
*Common Name:**	MHARZKPVSRQNNW-UHFFFAOYSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	MHARZKPVSRQNNW-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C18H10N2O2/c21-15-9-12-10-5-1-3-7-13(10)19-16(12)17-18(22)11-6-2-4-8-14(11)20(15)17/h1-9,19H
SMILES:	O=c1cc2c3ccccc3[nH]c2c2n1c1ccccc1c2=O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3309494
PubChem CID:	67809600
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000211] Indoles and derivatives [CHEMONTID:0001213] Pyridoindoles [CHEMONTID:0001374] Pyridoindolones

*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
NPO33161	hyrtios sp.	Species	Thorectidae	Eukaryota	n.a.	n.a.	n.a.	PMID[10514320]
NPO33161	hyrtios sp.	Species	Thorectidae	Eukaryota	n.a.	n.a.	n.a.	PMID[15497952]
NPO33161	hyrtios sp.	Species	Thorectidae	Eukaryota	n.a.	n.a.	n.a.	PMID[17378531]
NPO33161	hyrtios sp.	Species	Thorectidae	Eukaryota	n.a.	n.a.	n.a.	PMID[19167886]
NPO33161	hyrtios sp.	Species	Thorectidae	Eukaryota	n.a.	n.a.	n.a.	PMID[19783432]
NPO33161	hyrtios sp.	Species	Thorectidae	Eukaryota	n.a.	Australian	n.a.	PMID[24973030]
NPO33161	hyrtios sp.	Species	Thorectidae	Eukaryota	n.a.	n.a.	n.a.	PMID[28834433]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	2
Others	1

Activity Type	# Activity
Cell Line	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT858	Cell Line	LNCaP	Homo sapiens	IC50	=	22900.0	nM	PMID[553147]
NPT1523	Cell Line	NFF	Homo sapiens	IC50	=	32110.0	nM	PMID[553147]
NPT858	Cell Line	LNCaP	Homo sapiens	Ratio IC50	=	1.4	n.a.	PMID[553147]

☑ 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 NPC471943 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	744
0.1-0.2	6481
0.2-0.3	14996
0.3-0.4	14689
0.4-0.5	2104
0.5-0.6	2092
0.6-0.7	1298
0.7-0.8	233
0.8-0.85	38
0.85-0.9	17
0.9-0.95	4
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8935	High Similarity	NPC473666
0.875	High Similarity	NPC117027
0.8735	High Similarity	NPC284775
0.8613	High Similarity	NPC476460
0.8563	High Similarity	NPC151635
0.8554	High Similarity	NPC252572
0.8538	High Similarity	NPC133003
0.8521	High Similarity	NPC88110
0.848	Intermediate Similarity	NPC21429
0.8476	Intermediate Similarity	NPC115232
0.8448	Intermediate Similarity	NPC324091
0.8421	Intermediate Similarity	NPC470205
0.8266	Intermediate Similarity	NPC477003
0.8242	Intermediate Similarity	NPC214106
0.821	Intermediate Similarity	NPC295021
0.8202	Intermediate Similarity	NPC304203
0.8202	Intermediate Similarity	NPC326422
0.8197	Intermediate Similarity	NPC317701
0.8171	Intermediate Similarity	NPC135601
0.8171	Intermediate Similarity	NPC17273
0.8171	Intermediate Similarity	NPC141612
0.8118	Intermediate Similarity	NPC161861
0.8087	Intermediate Similarity	NPC471944
0.8061	Intermediate Similarity	NPC76982
0.805	Intermediate Similarity	NPC136002
0.7943	Intermediate Similarity	NPC191415
0.7912	Intermediate Similarity	NPC79356
0.7912	Intermediate Similarity	NPC102592
0.7886	Intermediate Similarity	NPC91179
0.7879	Intermediate Similarity	NPC281094
0.7877	Intermediate Similarity	NPC221873
0.7862	Intermediate Similarity	NPC471574
0.7861	Intermediate Similarity	NPC469529
0.7843	Intermediate Similarity	NPC209389
0.7814	Intermediate Similarity	NPC472293
0.7812	Intermediate Similarity	NPC238499
0.7809	Intermediate Similarity	NPC308931
0.7809	Intermediate Similarity	NPC99939
0.7772	Intermediate Similarity	NPC167710
0.7765	Intermediate Similarity	NPC8104
0.7764	Intermediate Similarity	NPC277157
0.7747	Intermediate Similarity	NPC472292
0.7738	Intermediate Similarity	NPC299594
0.7725	Intermediate Similarity	NPC471191
0.7719	Intermediate Similarity	NPC42372
0.7697	Intermediate Similarity	NPC102755
0.7688	Intermediate Similarity	NPC207554
0.7688	Intermediate Similarity	NPC477004
0.7688	Intermediate Similarity	NPC472297
0.7688	Intermediate Similarity	NPC472296
0.7668	Intermediate Similarity	NPC471193
0.7668	Intermediate Similarity	NPC471194
0.7661	Intermediate Similarity	NPC21174
0.7661	Intermediate Similarity	NPC271797
0.7644	Intermediate Similarity	NPC6982
0.7624	Intermediate Similarity	NPC17059
0.7622	Intermediate Similarity	NPC470440
0.7616	Intermediate Similarity	NPC71132
0.7576	Intermediate Similarity	NPC478186
0.7572	Intermediate Similarity	NPC114637
0.756	Intermediate Similarity	NPC200743
0.7558	Intermediate Similarity	NPC271734
0.7557	Intermediate Similarity	NPC293216
0.7548	Intermediate Similarity	NPC250361
0.7528	Intermediate Similarity	NPC11126
0.7526	Intermediate Similarity	NPC72956
0.7514	Intermediate Similarity	NPC472210
0.7514	Intermediate Similarity	NPC269886
0.7514	Intermediate Similarity	NPC247735
0.7514	Intermediate Similarity	NPC472295
0.7514	Intermediate Similarity	NPC81802
0.7487	Intermediate Similarity	NPC6865
0.7487	Intermediate Similarity	NPC153980
0.7486	Intermediate Similarity	NPC65080
0.7486	Intermediate Similarity	NPC73994
0.7484	Intermediate Similarity	NPC473930
0.7471	Intermediate Similarity	NPC470509
0.7468	Intermediate Similarity	NPC22079
0.7462	Intermediate Similarity	NPC322064
0.7459	Intermediate Similarity	NPC228835
0.7459	Intermediate Similarity	NPC47190
0.7455	Intermediate Similarity	NPC242556
0.7452	Intermediate Similarity	NPC473762
0.7421	Intermediate Similarity	NPC475450
0.7414	Intermediate Similarity	NPC233380
0.7407	Intermediate Similarity	NPC237414
0.7405	Intermediate Similarity	NPC473587
0.7403	Intermediate Similarity	NPC41174
0.7403	Intermediate Similarity	NPC254698
0.7398	Intermediate Similarity	NPC473218
0.7398	Intermediate Similarity	NPC470702
0.7394	Intermediate Similarity	NPC227582
0.738	Intermediate Similarity	NPC202812
0.7374	Intermediate Similarity	NPC471192
0.7371	Intermediate Similarity	NPC116555
0.736	Intermediate Similarity	NPC470703
0.7358	Intermediate Similarity	NPC475428
0.7351	Intermediate Similarity	NPC154339
0.7348	Intermediate Similarity	NPC470677
0.7333	Intermediate Similarity	NPC114033
0.7333	Intermediate Similarity	NPC58268
0.7333	Intermediate Similarity	NPC101130
0.7333	Intermediate Similarity	NPC129412
0.7321	Intermediate Similarity	NPC237649
0.7321	Intermediate Similarity	NPC300596
0.7316	Intermediate Similarity	NPC220797
0.7316	Intermediate Similarity	NPC474318
0.7316	Intermediate Similarity	NPC201266
0.7316	Intermediate Similarity	NPC74413
0.7316	Intermediate Similarity	NPC268744
0.7316	Intermediate Similarity	NPC153123
0.7316	Intermediate Similarity	NPC475914
0.7313	Intermediate Similarity	NPC323969
0.7312	Intermediate Similarity	NPC179365
0.7306	Intermediate Similarity	NPC132539
0.7299	Intermediate Similarity	NPC242116
0.7293	Intermediate Similarity	NPC16659
0.7293	Intermediate Similarity	NPC477042
0.7283	Intermediate Similarity	NPC160381
0.7283	Intermediate Similarity	NPC94752
0.7283	Intermediate Similarity	NPC475990
0.7278	Intermediate Similarity	NPC37548
0.7278	Intermediate Similarity	NPC473380
0.7278	Intermediate Similarity	NPC240088
0.7278	Intermediate Similarity	NPC124005
0.7277	Intermediate Similarity	NPC77241
0.7277	Intermediate Similarity	NPC269203
0.7277	Intermediate Similarity	NPC166209
0.7277	Intermediate Similarity	NPC13456
0.7277	Intermediate Similarity	NPC252338
0.7273	Intermediate Similarity	NPC67551
0.7273	Intermediate Similarity	NPC216550
0.7263	Intermediate Similarity	NPC131887
0.7262	Intermediate Similarity	NPC288838
0.7258	Intermediate Similarity	NPC472112
0.7257	Intermediate Similarity	NPC478184
0.725	Intermediate Similarity	NPC267811
0.7241	Intermediate Similarity	NPC220851
0.7239	Intermediate Similarity	NPC98156
0.7239	Intermediate Similarity	NPC167200
0.7239	Intermediate Similarity	NPC200397
0.7239	Intermediate Similarity	NPC292434
0.7239	Intermediate Similarity	NPC14448
0.7239	Intermediate Similarity	NPC138596
0.7239	Intermediate Similarity	NPC195704
0.7239	Intermediate Similarity	NPC64661
0.7238	Intermediate Similarity	NPC265710
0.7235	Intermediate Similarity	NPC471655
0.7234	Intermediate Similarity	NPC267343
0.7231	Intermediate Similarity	NPC243850
0.7228	Intermediate Similarity	NPC476341
0.7225	Intermediate Similarity	NPC81535
0.7225	Intermediate Similarity	NPC477887
0.7216	Intermediate Similarity	NPC2414
0.7212	Intermediate Similarity	NPC312092
0.7212	Intermediate Similarity	NPC471164
0.7209	Intermediate Similarity	NPC471458
0.7206	Intermediate Similarity	NPC229893
0.7204	Intermediate Similarity	NPC321708
0.7202	Intermediate Similarity	NPC260900
0.7196	Intermediate Similarity	NPC19692
0.7196	Intermediate Similarity	NPC220151
0.7195	Intermediate Similarity	NPC125746
0.7193	Intermediate Similarity	NPC117032
0.7184	Intermediate Similarity	NPC293487
0.7184	Intermediate Similarity	NPC135141
0.7184	Intermediate Similarity	NPC474492
0.7184	Intermediate Similarity	NPC92796
0.7182	Intermediate Similarity	NPC83774
0.7181	Intermediate Similarity	NPC272458
0.7178	Intermediate Similarity	NPC198988
0.7174	Intermediate Similarity	NPC110158
0.7169	Intermediate Similarity	NPC244087
0.7169	Intermediate Similarity	NPC97230
0.7169	Intermediate Similarity	NPC3698
0.7169	Intermediate Similarity	NPC77582
0.7169	Intermediate Similarity	NPC286529
0.7169	Intermediate Similarity	NPC209281
0.7169	Intermediate Similarity	NPC74928
0.7169	Intermediate Similarity	NPC205604
0.7169	Intermediate Similarity	NPC169308
0.7169	Intermediate Similarity	NPC12831
0.7169	Intermediate Similarity	NPC284635
0.7169	Intermediate Similarity	NPC48171
0.7169	Intermediate Similarity	NPC59839
0.7169	Intermediate Similarity	NPC302717
0.7169	Intermediate Similarity	NPC129753
0.7166	Intermediate Similarity	NPC314333
0.7164	Intermediate Similarity	NPC27041
0.7159	Intermediate Similarity	NPC478182
0.7151	Intermediate Similarity	NPC278434
0.7151	Intermediate Similarity	NPC262338
0.7143	Intermediate Similarity	NPC470680
0.7143	Intermediate Similarity	NPC100104
0.7135	Intermediate Similarity	NPC70949
0.7135	Intermediate Similarity	NPC53947
0.7128	Intermediate Similarity	NPC138370
0.712	Intermediate Similarity	NPC141454
0.7117	Intermediate Similarity	NPC300299
0.7115	Intermediate Similarity	NPC268534

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 NPC471943 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	411
0.1-0.2	715
0.2-0.3	965
0.3-0.4	2485
0.4-0.5	2192
0.5-0.6	1733
0.6-0.7	592
0.7-0.8	56
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8295	Intermediate Similarity	NPD6180	Clinical (unspecified phase)
0.7989	Intermediate Similarity	NPD5473	Discontinued
0.7912	Intermediate Similarity	NPD4848	Phase 1
0.7865	Intermediate Similarity	NPD4426	Clinical (unspecified phase)
0.7797	Intermediate Similarity	NPD3320	Approved
0.7797	Intermediate Similarity	NPD3319	Phase 1
0.7797	Intermediate Similarity	NPD3318	Approved
0.7654	Intermediate Similarity	NPD3607	Clinical (unspecified phase)
0.7554	Intermediate Similarity	NPD4922	Phase 2
0.7527	Intermediate Similarity	NPD4988	Discontinued
0.7526	Intermediate Similarity	NPD6176	Phase 1
0.7473	Intermediate Similarity	NPD5809	Phase 3
0.7416	Intermediate Similarity	NPD4075	Phase 2
0.7371	Intermediate Similarity	NPD2443	Approved
0.7371	Intermediate Similarity	NPD2442	Approved
0.7368	Intermediate Similarity	NPD8248	Clinical (unspecified phase)
0.7363	Intermediate Similarity	NPD7564	Discontinued
0.7358	Intermediate Similarity	NPD2008	Discontinued
0.7337	Intermediate Similarity	NPD3833	Phase 3
0.7337	Intermediate Similarity	NPD3835	Phase 3
0.7333	Intermediate Similarity	NPD2590	Clinical (unspecified phase)
0.7326	Intermediate Similarity	NPD4348	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD5592	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD2411	Approved
0.7293	Intermediate Similarity	NPD1291	Clinical (unspecified phase)
0.7287	Intermediate Similarity	NPD7619	Phase 3
0.7287	Intermediate Similarity	NPD7618	Phase 3
0.7283	Intermediate Similarity	NPD6217	Discontinued
0.7282	Intermediate Similarity	NPD2509	Approved
0.7282	Intermediate Similarity	NPD2510	Approved
0.7273	Intermediate Similarity	NPD3943	Clinical (unspecified phase)
0.7249	Intermediate Similarity	NPD1851	Clinical (unspecified phase)
0.7236	Intermediate Similarity	NPD3757	Clinical (unspecified phase)
0.7235	Intermediate Similarity	NPD4463	Approved
0.7235	Intermediate Similarity	NPD4462	Approved
0.7222	Intermediate Similarity	NPD4385	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD7455	Approved
0.7222	Intermediate Similarity	NPD7454	Approved
0.7216	Intermediate Similarity	NPD5901	Discontinued
0.7216	Intermediate Similarity	NPD6288	Clinical (unspecified phase)
0.7208	Intermediate Similarity	NPD7998	Clinical (unspecified phase)
0.7207	Intermediate Similarity	NPD3868	Phase 1
0.72	Intermediate Similarity	NPD5400	Approved
0.7195	Intermediate Similarity	NPD1262	Discovery
0.7194	Intermediate Similarity	NPD6459	Phase 2
0.7193	Intermediate Similarity	NPD3248	Phase 1
0.7191	Intermediate Similarity	NPD1573	Approved
0.7191	Intermediate Similarity	NPD1575	Approved
0.7189	Intermediate Similarity	NPD5820	Clinical (unspecified phase)
0.7184	Intermediate Similarity	NPD1630	Approved
0.7176	Intermediate Similarity	NPD4374	Clinical (unspecified phase)
0.7175	Intermediate Similarity	NPD4643	Clinical (unspecified phase)
0.7167	Intermediate Similarity	NPD4736	Clinical (unspecified phase)
0.7166	Intermediate Similarity	NPD4499	Approved
0.7158	Intermediate Similarity	NPD4011	Clinical (unspecified phase)
0.7157	Intermediate Similarity	NPD2408	Discontinued
0.7151	Intermediate Similarity	NPD4948	Discontinued
0.715	Intermediate Similarity	NPD7817	Phase 1
0.7143	Intermediate Similarity	NPD3077	Approved
0.7143	Intermediate Similarity	NPD5254	Discontinued
0.7143	Intermediate Similarity	NPD1920	Approved
0.7143	Intermediate Similarity	NPD3079	Approved
0.7143	Intermediate Similarity	NPD3076	Approved
0.7143	Intermediate Similarity	NPD3078	Approved
0.7143	Intermediate Similarity	NPD1919	Approved
0.7114	Intermediate Similarity	NPD3393	Approved
0.7114	Intermediate Similarity	NPD3394	Approved
0.7114	Intermediate Similarity	NPD4851	Clinical (unspecified phase)
0.7114	Intermediate Similarity	NPD3389	Approved
0.7104	Intermediate Similarity	NPD2481	Approved
0.7104	Intermediate Similarity	NPD2479	Phase 3
0.7086	Intermediate Similarity	NPD2214	Approved
0.7086	Intermediate Similarity	NPD2213	Approved
0.7081	Intermediate Similarity	NPD4300	Clinical (unspecified phase)
0.7077	Intermediate Similarity	NPD2121	Clinical (unspecified phase)
0.7071	Intermediate Similarity	NPD1600	Suspended
0.7062	Intermediate Similarity	NPD7727	Phase 2
0.7062	Intermediate Similarity	NPD1631	Approved
0.7059	Intermediate Similarity	NPD3961	Discontinued
0.7052	Intermediate Similarity	NPD2790	Discontinued
0.7045	Intermediate Similarity	NPD6454	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD5426	Phase 3
0.7041	Intermediate Similarity	NPD3947	Discontinued
0.7041	Intermediate Similarity	NPD8115	Approved
0.7041	Intermediate Similarity	NPD8114	Approved
0.7031	Intermediate Similarity	NPD6664	Approved
0.7031	Intermediate Similarity	NPD1952	Discontinued
0.7031	Intermediate Similarity	NPD2880	Discontinued
0.7022	Intermediate Similarity	NPD2915	Discontinued
0.7017	Intermediate Similarity	NPD4524	Discontinued
0.7016	Intermediate Similarity	NPD7024	Clinical (unspecified phase)
0.7015	Intermediate Similarity	NPD6787	Phase 2
0.7005	Intermediate Similarity	NPD4940	Approved
0.7	Intermediate Similarity	NPD4863	Approved
0.7	Intermediate Similarity	NPD1896	Approved
0.6995	Remote Similarity	NPD8000	Clinical (unspecified phase)
0.6984	Remote Similarity	NPD1905	Clinical (unspecified phase)
0.6982	Remote Similarity	NPD4637	Clinical (unspecified phase)
0.6979	Remote Similarity	NPD6449	Clinical (unspecified phase)
0.6978	Remote Similarity	NPD482	Approved
0.6978	Remote Similarity	NPD4883	Approved
0.6977	Remote Similarity	NPD3100	Discontinued
0.697	Remote Similarity	NPD1506	Discontinued
0.6968	Remote Similarity	NPD3246	Discontinued
0.6968	Remote Similarity	NPD6141	Clinical (unspecified phase)
0.6965	Remote Similarity	NPD7657	Approved
0.6965	Remote Similarity	NPD7656	Approved
0.6944	Remote Similarity	NPD2844	Phase 3
0.6941	Remote Similarity	NPD6017	Discontinued
0.694	Remote Similarity	NPD749	Clinical (unspecified phase)
0.6939	Remote Similarity	NPD2881	Approved
0.6939	Remote Similarity	NPD2879	Approved
0.6935	Remote Similarity	NPD7401	Clinical (unspecified phase)
0.6935	Remote Similarity	NPD5728	Clinical (unspecified phase)
0.6932	Remote Similarity	NPD4326	Phase 2
0.6928	Remote Similarity	NPD198	Clinical (unspecified phase)
0.6927	Remote Similarity	NPD5199	Approved
0.6927	Remote Similarity	NPD5198	Approved
0.6923	Remote Similarity	NPD1592	Phase 3
0.6919	Remote Similarity	NPD5146	Suspended
0.6915	Remote Similarity	NPD4614	Clinical (unspecified phase)
0.6909	Remote Similarity	NPD3385	Approved
0.6902	Remote Similarity	NPD6203	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD1854	Approved
0.6893	Remote Similarity	NPD6242	Discontinued
0.6891	Remote Similarity	NPD1871	Approved
0.6887	Remote Similarity	NPD6263	Clinical (unspecified phase)
0.6884	Remote Similarity	NPD3905	Phase 3
0.6884	Remote Similarity	NPD8493	Clinical (unspecified phase)
0.6884	Remote Similarity	NPD6838	Clinical (unspecified phase)
0.6872	Remote Similarity	NPD3583	Phase 2
0.6871	Remote Similarity	NPD947	Approved
0.6869	Remote Similarity	NPD4299	Phase 1
0.6869	Remote Similarity	NPD2721	Clinical (unspecified phase)
0.6866	Remote Similarity	NPD4051	Discontinued
0.686	Remote Similarity	NPD1528	Clinical (unspecified phase)
0.6859	Remote Similarity	NPD1658	Discontinued
0.6859	Remote Similarity	NPD6630	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD2837	Discontinued
0.6857	Remote Similarity	NPD4845	Discontinued
0.6851	Remote Similarity	NPD5069	Clinical (unspecified phase)
0.6851	Remote Similarity	NPD1343	Approved
0.6845	Remote Similarity	NPD2092	Phase 2
0.6845	Remote Similarity	NPD2094	Phase 2
0.6845	Remote Similarity	NPD2095	Phase 2
0.6839	Remote Similarity	NPD2172	Phase 1
0.6839	Remote Similarity	NPD7406	Phase 2
0.6837	Remote Similarity	NPD4500	Approved
0.6837	Remote Similarity	NPD4501	Approved
0.6834	Remote Similarity	NPD2715	Clinical (unspecified phase)
0.6833	Remote Similarity	NPD5744	Clinical (unspecified phase)
0.6832	Remote Similarity	NPD5475	Discontinued
0.6828	Remote Similarity	NPD8464	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD1722	Approved
0.6821	Remote Similarity	NPD4987	Clinical (unspecified phase)
0.6812	Remote Similarity	NPD6579	Phase 2
0.6811	Remote Similarity	NPD3505	Approved
0.6811	Remote Similarity	NPD3506	Approved
0.6809	Remote Similarity	NPD2091	Phase 2
0.6809	Remote Similarity	NPD2096	Phase 2
0.6805	Remote Similarity	NPD786	Approved
0.6805	Remote Similarity	NPD569	Clinical (unspecified phase)
0.6802	Remote Similarity	NPD1524	Phase 1
0.6802	Remote Similarity	NPD5017	Discontinued
0.68	Remote Similarity	NPD8322	Phase 2
0.68	Remote Similarity	NPD5965	Clinical (unspecified phase)
0.6793	Remote Similarity	NPD1586	Approved
0.6789	Remote Similarity	NPD2009	Clinical (unspecified phase)
0.6788	Remote Similarity	NPD1541	Approved
0.6786	Remote Similarity	NPD7000	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD45	Approved
0.6786	Remote Similarity	NPD7621	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD6999	Discontinued
0.6786	Remote Similarity	NPD6554	Approved
0.6784	Remote Similarity	NPD6987	Phase 1
0.6782	Remote Similarity	NPD7809	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD4076	Approved
0.6774	Remote Similarity	NPD4079	Approved
0.6774	Remote Similarity	NPD3239	Clinical (unspecified phase)
0.6771	Remote Similarity	NPD2336	Approved
0.6766	Remote Similarity	NPD4880	Discontinued
0.6758	Remote Similarity	NPD1292	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD5104	Approved
0.6754	Remote Similarity	NPD5016	Approved
0.6754	Remote Similarity	NPD1284	Clinical (unspecified phase)
0.6754	Remote Similarity	NPD4334	Discontinued
0.6754	Remote Similarity	NPD1534	Approved
0.6749	Remote Similarity	NPD8013	Clinical (unspecified phase)
0.6749	Remote Similarity	NPD7470	Discontinued
0.6749	Remote Similarity	NPD6567	Clinical (unspecified phase)
0.6745	Remote Similarity	NPD7781	Approved
0.6745	Remote Similarity	NPD7780	Approved
0.6739	Remote Similarity	NPD750	Phase 2
0.6738	Remote Similarity	NPD6277	Clinical (unspecified phase)
0.6738	Remote Similarity	NPD6595	Phase 3
0.6737	Remote Similarity	NPD5444	Phase 1
0.6735	Remote Similarity	NPD1982	Phase 1
0.6733	Remote Similarity	NPD4506	Discontinued
0.6732	Remote Similarity	NPD5293	Phase 2
0.6726	Remote Similarity	NPD1256	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