NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	236.06
Volume:	234.957
LogP:	1.883
LogD:	2.002
LogS:	-3.731
# Rotatable Bonds:	0
TPSA:	54.6
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.509
Synthetic Accessibility Score:	2.433
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:	-4.688
MDCK Permeability:	2.1469240891747177e-05
Pgp-inhibitor:	0.004
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.046
30% Bioavailability (F30%):	0.068

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.611
Plasma Protein Binding (PPB):	91.1201400756836%
Volume Distribution (VD):	0.69
Pgp-substrate:	4.150381088256836%

ADMET: Metabolism

CYP1A2-inhibitor:	0.99
CYP1A2-substrate:	0.265
CYP2C19-inhibitor:	0.312
CYP2C19-substrate:	0.141
CYP2C9-inhibitor:	0.243
CYP2C9-substrate:	0.931
CYP2D6-inhibitor:	0.489
CYP2D6-substrate:	0.9
CYP3A4-inhibitor:	0.609
CYP3A4-substrate:	0.181

ADMET: Excretion

Clearance (CL):	8.246
Half-life (T1/2):	0.801

ADMET: Toxicity

hERG Blockers:	0.104
Human Hepatotoxicity (H-HT):	0.565
Drug-inuced Liver Injury (DILI):	0.787
AMES Toxicity:	0.95
Rat Oral Acute Toxicity:	0.045
Maximum Recommended Daily Dose:	0.959
Skin Sensitization:	0.179
Carcinogencity:	0.967
Eye Corrosion:	0.003
Eye Irritation:	0.802
Respiratory Toxicity:	0.801

Download Data

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

Natural Product: NPC211813

Natural Product ID:	NPC211813
*Common Name:**	FZLISVGXWLVEPB-UHFFFAOYSA-N
IUPAC Name:	n.a.
Synonyms:	NSC-341583
Standard InCHIKey:	FZLISVGXWLVEPB-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C14H8N2O2/c17-8-1-3-12-10(7-8)9-5-6-15-11-2-4-13(18)16(12)14(9)11/h1-7,17H
SMILES:	Oc1ccc2c(c1)c1ccnc3c1n2c(=O)cc3
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL454311
PubChem CID:	158929
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids and derivatives [CHEMONTID:0003805] Indolonaphthyridine alkaloids

*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
NPO20931	Simaba multiflora	Species	Simaroubaceae	Eukaryota	n.a.	xylem	n.a.	DOI[10.1016/S0040-4039(00)86970-1]
NPO20931	Simaba multiflora	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17340534]
NPO20931	Simaba multiflora	Species	Simaroubaceae	Eukaryota	Fruits	n.a.	n.a.	PMID[3760884]
NPO20931	Simaba multiflora	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[6736970]
NPO20931	Simaba multiflora	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[6875576]
NPO20931	Simaba multiflora	Species	Simaroubaceae	Eukaryota	n.a.	xylem	n.a.	PMID[6875577]
NPO20931	Simaba multiflora	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[6875577]
NPO20931	Simaba multiflora	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

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

NP Quantity Composition/Concentration

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

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

Biological Activity

Activity Type	# Activity
ED50	1
MIC	5

Activity Type	# Activity
Cell Line	1
Organism	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	ED50	=	2.2	ug ml-1	PMID[522738]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	>	64.0	ug.mL-1	PMID[522739]
NPT314	Organism	Bacillus cereus	Bacillus cereus	MIC	=	16.0	ug.mL-1	PMID[522739]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	>	64.0	ug.mL-1	PMID[522739]
NPT331	Organism	Ralstonia solanacearum	Ralstonia solanacearum	MIC	>	64.0	ug.mL-1	PMID[522739]

☑ 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 NPC211813 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	678
0.1-0.2	3804
0.2-0.3	13094
0.3-0.4	9798
0.4-0.5	10653
0.5-0.6	2255
0.6-0.7	1984
0.7-0.8	392
0.8-0.85	27
0.85-0.9	6
0.9-0.95	5
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9405	High Similarity	NPC200836
0.9405	High Similarity	NPC53144
0.9206	High Similarity	NPC82548
0.911	High Similarity	NPC85273
0.8667	High Similarity	NPC174672
0.8667	High Similarity	NPC174758
0.8653	High Similarity	NPC475070
0.8534	High Similarity	NPC212213
0.8513	High Similarity	NPC476124
0.8513	High Similarity	NPC476121
0.8434	Intermediate Similarity	NPC5145
0.8426	Intermediate Similarity	NPC287208
0.8408	Intermediate Similarity	NPC274982
0.8342	Intermediate Similarity	NPC192315
0.8342	Intermediate Similarity	NPC239954
0.8325	Intermediate Similarity	NPC198673
0.8299	Intermediate Similarity	NPC476167
0.8255	Intermediate Similarity	NPC477549
0.8245	Intermediate Similarity	NPC314002
0.8235	Intermediate Similarity	NPC220765
0.8226	Intermediate Similarity	NPC24864
0.8201	Intermediate Similarity	NPC171171
0.8191	Intermediate Similarity	NPC204717
0.8186	Intermediate Similarity	NPC476041
0.8186	Intermediate Similarity	NPC304926
0.8177	Intermediate Similarity	NPC99666
0.8177	Intermediate Similarity	NPC324149
0.8163	Intermediate Similarity	NPC176538
0.8156	Intermediate Similarity	NPC293487
0.8154	Intermediate Similarity	NPC168911
0.8113	Intermediate Similarity	NPC207686
0.81	Intermediate Similarity	NPC53344
0.8022	Intermediate Similarity	NPC478182
0.8021	Intermediate Similarity	NPC184964
0.801	Intermediate Similarity	NPC156704
0.801	Intermediate Similarity	NPC77555
0.801	Intermediate Similarity	NPC270918
0.799	Intermediate Similarity	NPC57398
0.7967	Intermediate Similarity	NPC478185
0.7949	Intermediate Similarity	NPC329541
0.7946	Intermediate Similarity	NPC32534
0.7935	Intermediate Similarity	NPC478183
0.7925	Intermediate Similarity	NPC6215
0.7923	Intermediate Similarity	NPC469727
0.7923	Intermediate Similarity	NPC478184
0.791	Intermediate Similarity	NPC470500
0.7889	Intermediate Similarity	NPC315491
0.7889	Intermediate Similarity	NPC45459
0.7889	Intermediate Similarity	NPC213308
0.7884	Intermediate Similarity	NPC12649
0.7879	Intermediate Similarity	NPC474916
0.7876	Intermediate Similarity	NPC46580
0.7854	Intermediate Similarity	NPC99891
0.7837	Intermediate Similarity	NPC27041
0.7828	Intermediate Similarity	NPC90229
0.7811	Intermediate Similarity	NPC470678
0.78	Intermediate Similarity	NPC249040
0.7788	Intermediate Similarity	NPC97902
0.7783	Intermediate Similarity	NPC474145
0.7783	Intermediate Similarity	NPC475841
0.7778	Intermediate Similarity	NPC316181
0.7778	Intermediate Similarity	NPC151781
0.7778	Intermediate Similarity	NPC74562
0.7772	Intermediate Similarity	NPC223427
0.7763	Intermediate Similarity	NPC41679
0.7762	Intermediate Similarity	NPC213530
0.7762	Intermediate Similarity	NPC193267
0.7756	Intermediate Similarity	NPC476116
0.7754	Intermediate Similarity	NPC314940
0.7754	Intermediate Similarity	NPC473764
0.7754	Intermediate Similarity	NPC91895
0.7734	Intermediate Similarity	NPC472259
0.7729	Intermediate Similarity	NPC219087
0.7727	Intermediate Similarity	NPC276517
0.7725	Intermediate Similarity	NPC276657
0.7718	Intermediate Similarity	NPC309845
0.7717	Intermediate Similarity	NPC25899
0.771	Intermediate Similarity	NPC60006
0.7707	Intermediate Similarity	NPC171787
0.7703	Intermediate Similarity	NPC8022
0.7703	Intermediate Similarity	NPC470799
0.7688	Intermediate Similarity	NPC251090
0.7688	Intermediate Similarity	NPC242209
0.7685	Intermediate Similarity	NPC245816
0.7685	Intermediate Similarity	NPC476138
0.7685	Intermediate Similarity	NPC476098
0.7677	Intermediate Similarity	NPC307963
0.7676	Intermediate Similarity	NPC48192
0.7673	Intermediate Similarity	NPC232727
0.7671	Intermediate Similarity	NPC295228
0.7668	Intermediate Similarity	NPC48938
0.7664	Intermediate Similarity	NPC245348
0.7659	Intermediate Similarity	NPC88008
0.7653	Intermediate Similarity	NPC32771
0.765	Intermediate Similarity	NPC267928
0.765	Intermediate Similarity	NPC476451
0.7638	Intermediate Similarity	NPC326634
0.7635	Intermediate Similarity	NPC295898
0.7634	Intermediate Similarity	NPC178858
0.763	Intermediate Similarity	NPC264285
0.7628	Intermediate Similarity	NPC214980
0.7619	Intermediate Similarity	NPC252590
0.761	Intermediate Similarity	NPC472111
0.7608	Intermediate Similarity	NPC476287
0.7606	Intermediate Similarity	NPC60621
0.7604	Intermediate Similarity	NPC88363
0.7598	Intermediate Similarity	NPC475774
0.7594	Intermediate Similarity	NPC471178
0.7576	Intermediate Similarity	NPC92111
0.7574	Intermediate Similarity	NPC81535
0.7573	Intermediate Similarity	NPC193238
0.7563	Intermediate Similarity	NPC296527
0.7556	Intermediate Similarity	NPC478186
0.7546	Intermediate Similarity	NPC103687
0.7546	Intermediate Similarity	NPC132631
0.754	Intermediate Similarity	NPC97367
0.7536	Intermediate Similarity	NPC477111
0.7534	Intermediate Similarity	NPC81175
0.7525	Intermediate Similarity	NPC76748
0.7524	Intermediate Similarity	NPC477113
0.7524	Intermediate Similarity	NPC477610
0.7513	Intermediate Similarity	NPC72980
0.7511	Intermediate Similarity	NPC472434
0.75	Intermediate Similarity	NPC473312
0.75	Intermediate Similarity	NPC295452
0.75	Intermediate Similarity	NPC141053
0.75	Intermediate Similarity	NPC171393
0.75	Intermediate Similarity	NPC185782
0.7488	Intermediate Similarity	NPC237740
0.7477	Intermediate Similarity	NPC184225
0.7476	Intermediate Similarity	NPC264166
0.7476	Intermediate Similarity	NPC274291
0.7476	Intermediate Similarity	NPC47059
0.7476	Intermediate Similarity	NPC118832
0.7476	Intermediate Similarity	NPC329708
0.7476	Intermediate Similarity	NPC165349
0.7475	Intermediate Similarity	NPC474188
0.7474	Intermediate Similarity	NPC271792
0.7464	Intermediate Similarity	NPC123976
0.7464	Intermediate Similarity	NPC167860
0.7462	Intermediate Similarity	NPC62749
0.7461	Intermediate Similarity	NPC96890
0.746	Intermediate Similarity	NPC56233
0.7456	Intermediate Similarity	NPC26543
0.7454	Intermediate Similarity	NPC130570
0.7453	Intermediate Similarity	NPC477110
0.7453	Intermediate Similarity	NPC322064
0.7452	Intermediate Similarity	NPC18348
0.7451	Intermediate Similarity	NPC19872
0.7451	Intermediate Similarity	NPC234197
0.7451	Intermediate Similarity	NPC315957
0.7442	Intermediate Similarity	NPC310118
0.7441	Intermediate Similarity	NPC266931
0.7438	Intermediate Similarity	NPC470499
0.7431	Intermediate Similarity	NPC157931
0.743	Intermediate Similarity	NPC74360
0.7429	Intermediate Similarity	NPC208284
0.7426	Intermediate Similarity	NPC222018
0.7422	Intermediate Similarity	NPC39092
0.7407	Intermediate Similarity	NPC16352
0.7407	Intermediate Similarity	NPC220851
0.7398	Intermediate Similarity	NPC176127
0.7394	Intermediate Similarity	NPC59779
0.7394	Intermediate Similarity	NPC124542
0.7394	Intermediate Similarity	NPC471177
0.7393	Intermediate Similarity	NPC26679
0.7391	Intermediate Similarity	NPC285558
0.7385	Intermediate Similarity	NPC319232
0.7385	Intermediate Similarity	NPC24370
0.7376	Intermediate Similarity	NPC279189
0.7376	Intermediate Similarity	NPC200553
0.7373	Intermediate Similarity	NPC122436
0.7371	Intermediate Similarity	NPC326575
0.7364	Intermediate Similarity	NPC326363
0.7352	Intermediate Similarity	NPC470126
0.7349	Intermediate Similarity	NPC17565
0.7347	Intermediate Similarity	NPC314394
0.734	Intermediate Similarity	NPC131718
0.7333	Intermediate Similarity	NPC248462
0.7333	Intermediate Similarity	NPC60553
0.7333	Intermediate Similarity	NPC477861
0.7327	Intermediate Similarity	NPC106937
0.7327	Intermediate Similarity	NPC470501
0.7326	Intermediate Similarity	NPC129721
0.7323	Intermediate Similarity	NPC295158
0.7321	Intermediate Similarity	NPC183777
0.732	Intermediate Similarity	NPC150048
0.732	Intermediate Similarity	NPC203754
0.7317	Intermediate Similarity	NPC287437
0.7315	Intermediate Similarity	NPC472099
0.7311	Intermediate Similarity	NPC112206
0.7311	Intermediate Similarity	NPC316981
0.7311	Intermediate Similarity	NPC472098
0.7311	Intermediate Similarity	NPC471603
0.7311	Intermediate Similarity	NPC202605
0.7309	Intermediate Similarity	NPC182222
0.7309	Intermediate Similarity	NPC325976
0.7309	Intermediate Similarity	NPC253675
0.7308	Intermediate Similarity	NPC74619
0.7306	Intermediate Similarity	NPC471294

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 NPC211813 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	384
0.1-0.2	610
0.2-0.3	882
0.3-0.4	1587
0.4-0.5	2661
0.5-0.6	1925
0.6-0.7	971
0.7-0.8	127
0.8-0.85	3
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8421	Intermediate Similarity	NPD5575	Clinical (unspecified phase)
0.816	Intermediate Similarity	NPD5040	Clinical (unspecified phase)
0.8148	Intermediate Similarity	NPD6344	Clinical (unspecified phase)
0.8049	Intermediate Similarity	NPD7112	Discontinued
0.8009	Intermediate Similarity	NPD4845	Discontinued
0.7889	Intermediate Similarity	NPD484	Approved
0.7826	Intermediate Similarity	NPD4897	Phase 2
0.7703	Intermediate Similarity	NPD6803	Clinical (unspecified phase)
0.7677	Intermediate Similarity	NPD1304	Clinical (unspecified phase)
0.7677	Intermediate Similarity	NPD1038	Approved
0.7662	Intermediate Similarity	NPD6999	Discontinued
0.7662	Intermediate Similarity	NPD7000	Clinical (unspecified phase)
0.7659	Intermediate Similarity	NPD7222	Phase 2
0.765	Intermediate Similarity	NPD7948	Phase 1
0.763	Intermediate Similarity	NPD8405	Clinical (unspecified phase)
0.7628	Intermediate Similarity	NPD7603	Discontinued
0.7614	Intermediate Similarity	NPD3321	Discontinued
0.7606	Intermediate Similarity	NPD5506	Approved
0.7606	Intermediate Similarity	NPD5507	Approved
0.7561	Intermediate Similarity	NPD4795	Phase 2
0.7559	Intermediate Similarity	NPD6242	Discontinued
0.7553	Intermediate Similarity	NPD425	Approved
0.7553	Intermediate Similarity	NPD424	Approved
0.7539	Intermediate Similarity	NPD9690	Approved
0.7536	Intermediate Similarity	NPD7666	Phase 3
0.7536	Intermediate Similarity	NPD7665	Phase 2
0.7527	Intermediate Similarity	NPD9705	Discontinued
0.7527	Intermediate Similarity	NPD112	Approved
0.75	Intermediate Similarity	NPD2762	Phase 2
0.75	Intermediate Similarity	NPD926	Approved
0.75	Intermediate Similarity	NPD9695	Approved
0.75	Intermediate Similarity	NPD925	Approved
0.7488	Intermediate Similarity	NPD7452	Approved
0.7488	Intermediate Similarity	NPD7453	Approved
0.7477	Intermediate Similarity	NPD5559	Phase 2
0.7476	Intermediate Similarity	NPD32	Approved
0.7476	Intermediate Similarity	NPD4122	Approved
0.7476	Intermediate Similarity	NPD4034	Approved
0.7476	Intermediate Similarity	NPD4039	Approved
0.7476	Intermediate Similarity	NPD4035	Approved
0.7476	Intermediate Similarity	NPD4038	Approved
0.7476	Intermediate Similarity	NPD4036	Approved
0.7476	Intermediate Similarity	NPD4033	Approved
0.7476	Intermediate Similarity	NPD31	Approved
0.7476	Intermediate Similarity	NPD4037	Approved
0.7475	Intermediate Similarity	NPD6965	Clinical (unspecified phase)
0.7463	Intermediate Similarity	NPD4418	Discontinued
0.7452	Intermediate Similarity	NPD2916	Discontinued
0.7451	Intermediate Similarity	NPD1740	Approved
0.7451	Intermediate Similarity	NPD1739	Approved
0.7448	Intermediate Similarity	NPD5065	Approved
0.744	Intermediate Similarity	NPD5601	Phase 2
0.7398	Intermediate Similarity	NPD5522	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD5901	Discontinued
0.7379	Intermediate Similarity	NPD6975	Discontinued
0.7371	Intermediate Similarity	NPD5612	Discontinued
0.7356	Intermediate Similarity	NPD5530	Phase 1
0.7344	Intermediate Similarity	NPD5934	Clinical (unspecified phase)
0.7343	Intermediate Similarity	NPD4886	Phase 2
0.7337	Intermediate Similarity	NPD2383	Phase 1
0.7336	Intermediate Similarity	NPD4558	Phase 2
0.7336	Intermediate Similarity	NPD7823	Clinical (unspecified phase)
0.733	Intermediate Similarity	NPD2781	Approved
0.7327	Intermediate Similarity	NPD802	Phase 2
0.7323	Intermediate Similarity	NPD2814	Clinical (unspecified phase)
0.7321	Intermediate Similarity	NPD1197	Approved
0.7316	Intermediate Similarity	NPD2780	Approved
0.7316	Intermediate Similarity	NPD2782	Approved
0.7285	Intermediate Similarity	NPD7589	Clinical (unspecified phase)
0.7282	Intermediate Similarity	NPD6159	Phase 2
0.7281	Intermediate Similarity	NPD5483	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD7001	Phase 3
0.7273	Intermediate Similarity	NPD6732	Clinical (unspecified phase)
0.7259	Intermediate Similarity	NPD4203	Approved
0.7259	Intermediate Similarity	NPD4204	Approved
0.724	Intermediate Similarity	NPD7710	Clinical (unspecified phase)
0.7238	Intermediate Similarity	NPD6838	Clinical (unspecified phase)
0.7232	Intermediate Similarity	NPD2757	Phase 2
0.7222	Intermediate Similarity	NPD3354	Phase 2
0.722	Intermediate Similarity	NPD7797	Approved
0.722	Intermediate Similarity	NPD7796	Approved
0.7212	Intermediate Similarity	NPD3928	Approved
0.7212	Intermediate Similarity	NPD3931	Approved
0.7206	Intermediate Similarity	NPD7944	Discontinued
0.7205	Intermediate Similarity	NPD3962	Phase 2
0.7205	Intermediate Similarity	NPD3959	Phase 2
0.7204	Intermediate Similarity	NPD5658	Approved
0.7204	Intermediate Similarity	NPD2882	Phase 1
0.7196	Intermediate Similarity	NPD5255	Approved
0.7192	Intermediate Similarity	NPD3923	Approved
0.7192	Intermediate Similarity	NPD3922	Approved
0.7192	Intermediate Similarity	NPD3924	Approved
0.7192	Intermediate Similarity	NPD3921	Approved
0.719	Intermediate Similarity	NPD4901	Clinical (unspecified phase)
0.7182	Intermediate Similarity	NPD7586	Clinical (unspecified phase)
0.7163	Intermediate Similarity	NPD4511	Phase 1
0.715	Intermediate Similarity	NPD4118	Clinical (unspecified phase)
0.715	Intermediate Similarity	NPD5555	Phase 1
0.715	Intermediate Similarity	NPD3330	Phase 1
0.7149	Intermediate Similarity	NPD6961	Discontinued
0.7143	Intermediate Similarity	NPD5100	Phase 3
0.7143	Intermediate Similarity	NPD5426	Phase 3
0.7143	Intermediate Similarity	NPD6375	Clinical (unspecified phase)
0.713	Intermediate Similarity	NPD5801	Clinical (unspecified phase)
0.7121	Intermediate Similarity	NPD6452	Discontinued
0.7112	Intermediate Similarity	NPD6158	Phase 2
0.7112	Intermediate Similarity	NPD9706	Clinical (unspecified phase)
0.7112	Intermediate Similarity	NPD6476	Clinical (unspecified phase)
0.711	Intermediate Similarity	NPD3258	Approved
0.7109	Intermediate Similarity	NPD3932	Clinical (unspecified phase)
0.7108	Intermediate Similarity	NPD4372	Phase 1
0.7108	Intermediate Similarity	NPD6569	Phase 2
0.7105	Intermediate Similarity	NPD7025	Clinical (unspecified phase)
0.7094	Intermediate Similarity	NPD1213	Phase 3
0.7091	Intermediate Similarity	NPD1856	Discontinued
0.7085	Intermediate Similarity	NPD7414	Clinical (unspecified phase)
0.7082	Intermediate Similarity	NPD3809	Discontinued
0.708	Intermediate Similarity	NPD6970	Phase 2
0.7079	Intermediate Similarity	NPD6141	Clinical (unspecified phase)
0.7072	Intermediate Similarity	NPD7426	Phase 1
0.707	Intermediate Similarity	NPD3815	Phase 1
0.707	Intermediate Similarity	NPD3816	Phase 1
0.7065	Intermediate Similarity	NPD3813	Approved
0.7065	Intermediate Similarity	NPD4336	Clinical (unspecified phase)
0.7056	Intermediate Similarity	NPD4900	Clinical (unspecified phase)
0.7043	Intermediate Similarity	NPD1661	Suspended
0.7042	Intermediate Similarity	NPD6376	Discontinued
0.7041	Intermediate Similarity	NPD750	Phase 2
0.7039	Intermediate Similarity	NPD3324	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD3243	Approved
0.7035	Intermediate Similarity	NPD6223	Clinical (unspecified phase)
0.7033	Intermediate Similarity	NPD6389	Clinical (unspecified phase)
0.7033	Intermediate Similarity	NPD4396	Clinical (unspecified phase)
0.7032	Intermediate Similarity	NPD7203	Clinical (unspecified phase)
0.7031	Intermediate Similarity	NPD8017	Clinical (unspecified phase)
0.7031	Intermediate Similarity	NPD8016	Phase 3
0.7031	Intermediate Similarity	NPD2921	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD706	Phase 1
0.7024	Intermediate Similarity	NPD9689	Approved
0.7024	Intermediate Similarity	NPD3404	Approved
0.7014	Intermediate Similarity	NPD6824	Clinical (unspecified phase)
0.701	Intermediate Similarity	NPD6281	Approved
0.7009	Intermediate Similarity	NPD8101	Phase 3
0.7009	Intermediate Similarity	NPD7555	Discontinued
0.7005	Intermediate Similarity	NPD3257	Approved
0.7005	Intermediate Similarity	NPD6492	Phase 2
0.7	Intermediate Similarity	NPD5827	Discontinued
0.7	Intermediate Similarity	NPD6856	Discontinued
0.7	Intermediate Similarity	NPD6790	Phase 1
0.6995	Remote Similarity	NPD3930	Clinical (unspecified phase)
0.6995	Remote Similarity	NPD4948	Discontinued
0.6992	Remote Similarity	NPD8463	Approved
0.6991	Remote Similarity	NPD4852	Phase 2
0.6987	Remote Similarity	NPD7923	Phase 2
0.6986	Remote Similarity	NPD3825	Phase 3
0.6986	Remote Similarity	NPD2177	Approved
0.6986	Remote Similarity	NPD2175	Phase 3
0.6986	Remote Similarity	NPD2176	Approved
0.6985	Remote Similarity	NPD1503	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD7712	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD6138	Clinical (unspecified phase)
0.698	Remote Similarity	NPD4889	Approved
0.698	Remote Similarity	NPD7424	Clinical (unspecified phase)
0.6976	Remote Similarity	NPD2336	Approved
0.6975	Remote Similarity	NPD8091	Phase 3
0.6974	Remote Similarity	NPD6872	Clinical (unspecified phase)
0.6971	Remote Similarity	NPD2952	Discontinued
0.6963	Remote Similarity	NPD2189	Approved
0.6963	Remote Similarity	NPD2187	Approved
0.6961	Remote Similarity	NPD4334	Discontinued
0.6959	Remote Similarity	NPD2720	Phase 1
0.6959	Remote Similarity	NPD1322	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD2719	Clinical (unspecified phase)
0.6942	Remote Similarity	NPD5505	Discontinued
0.694	Remote Similarity	NPD7068	Approved
0.694	Remote Similarity	NPD7067	Approved
0.6937	Remote Similarity	NPD8356	Approved
0.6935	Remote Similarity	NPD5751	Clinical (unspecified phase)
0.6934	Remote Similarity	NPD5513	Phase 2
0.6934	Remote Similarity	NPD4044	Discontinued
0.6927	Remote Similarity	NPD3439	Approved
0.6923	Remote Similarity	NPD6276	Discontinued
0.6923	Remote Similarity	NPD7818	Clinical (unspecified phase)
0.692	Remote Similarity	NPD4926	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD5017	Discontinued
0.6917	Remote Similarity	NPD5867	Clinical (unspecified phase)
0.6917	Remote Similarity	NPD6531	Approved
0.6917	Remote Similarity	NPD6530	Approved
0.6908	Remote Similarity	NPD4551	Phase 2
0.6905	Remote Similarity	NPD6137	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD8396	Approved
0.6905	Remote Similarity	NPD3814	Phase 1
0.6905	Remote Similarity	NPD8395	Approved
0.6904	Remote Similarity	NPD1078	Clinical (unspecified phase)
0.6903	Remote Similarity	NPD7567	Approved
0.6903	Remote Similarity	NPD6969	Phase 2
0.6903	Remote Similarity	NPD6968	Phase 2
0.6901	Remote Similarity	NPD6987	Phase 1
0.6897	Remote Similarity	NPD6610	Clinical (unspecified phase)
0.6893	Remote Similarity	NPD6022	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