NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	265.06
Volume:	246.915
LogP:	1.388
LogD:	0.184
LogS:	-2.702
# Rotatable Bonds:	1
TPSA:	147.4
# H-Bond Aceptor:	7
# H-Bond Donor:	8
# Rings:	2
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.233
Synthetic Accessibility Score:	3.431
Fsp3:	0.0
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	2
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.291
MDCK Permeability:	4.088497007614933e-06
Pgp-inhibitor:	0.009
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.047
20% Bioavailability (F20%):	0.607
30% Bioavailability (F30%):	0.983

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.006
Plasma Protein Binding (PPB):	97.8062744140625%
Volume Distribution (VD):	0.625
Pgp-substrate:	8.496209144592285%

ADMET: Metabolism

CYP1A2-inhibitor:	0.261
CYP1A2-substrate:	0.119
CYP2C19-inhibitor:	0.016
CYP2C19-substrate:	0.053
CYP2C9-inhibitor:	0.157
CYP2C9-substrate:	0.312
CYP2D6-inhibitor:	0.028
CYP2D6-substrate:	0.171
CYP3A4-inhibitor:	0.016
CYP3A4-substrate:	0.02

ADMET: Excretion

Clearance (CL):	6.433
Half-life (T1/2):	0.87

ADMET: Toxicity

hERG Blockers:	0.024
Human Hepatotoxicity (H-HT):	0.182
Drug-inuced Liver Injury (DILI):	0.872
AMES Toxicity:	0.259
Rat Oral Acute Toxicity:	0.006
Maximum Recommended Daily Dose:	0.238
Skin Sensitization:	0.951
Carcinogencity:	0.193
Eye Corrosion:	0.008
Eye Irritation:	0.892
Respiratory Toxicity:	0.076

Download Data

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

Natural Product: NPC4331

Natural Product ID:	NPC4331
*Common Name:**	Echinamine B
IUPAC Name:	n.a.
Synonyms:	Echinamine B
Standard InCHIKey:	ZYAIBKURUKIHGU-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C12H11NO6/c1-2-3-7(14)4-5(10(17)8(3)15)11(18)12(19)6(13)9(4)16/h14-15,17,19H,2,13H2,1H3
SMILES:	CCc1c(c2c(c(c1O)O)C(=O)C(=C(C2=O)N)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL464307
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000023] Naphthalenes [CHEMONTID:0000153] Naphthoquinones

*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
NPO3125	Scaphechinus mirabilis	Species	Scutellidae	Eukaryota	n.a.	n.a.	n.a.	PMID[16180820]
NPO3125	Scaphechinus mirabilis	Species	Scutellidae	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
EC50	1

Activity Type	# Activity
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1	Others	Radical scavenging activity		EC50	=	10000.0	nM	PMID[496550]

☑ 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 NPC4331 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	330
0.1-0.2	1827
0.2-0.3	6540
0.3-0.4	12594
0.4-0.5	6902
0.5-0.6	8097
0.6-0.7	5990
0.7-0.8	408
0.8-0.85	5
0.85-0.9	2
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC96160
0.8767	High Similarity	NPC14377
0.8224	Intermediate Similarity	NPC123714
0.8182	Intermediate Similarity	NPC92079
0.8146	Intermediate Similarity	NPC129752
0.8013	Intermediate Similarity	NPC291078
0.7848	Intermediate Similarity	NPC238629
0.7811	Intermediate Similarity	NPC54661
0.7811	Intermediate Similarity	NPC163924
0.7806	Intermediate Similarity	NPC238108
0.7742	Intermediate Similarity	NPC471690
0.7707	Intermediate Similarity	NPC143438
0.7658	Intermediate Similarity	NPC203063
0.7636	Intermediate Similarity	NPC161778
0.7632	Intermediate Similarity	NPC278928
0.7622	Intermediate Similarity	NPC103509
0.7619	Intermediate Similarity	NPC472046
0.7607	Intermediate Similarity	NPC112816
0.7607	Intermediate Similarity	NPC471907
0.7597	Intermediate Similarity	NPC88864
0.759	Intermediate Similarity	NPC273248
0.758	Intermediate Similarity	NPC147418
0.756	Intermediate Similarity	NPC283301
0.7547	Intermediate Similarity	NPC187690
0.7544	Intermediate Similarity	NPC29055
0.7544	Intermediate Similarity	NPC173587
0.7544	Intermediate Similarity	NPC208120
0.7532	Intermediate Similarity	NPC416
0.7532	Intermediate Similarity	NPC61398
0.7516	Intermediate Similarity	NPC254847
0.7515	Intermediate Similarity	NPC48949
0.7515	Intermediate Similarity	NPC280295
0.75	Intermediate Similarity	NPC110810
0.75	Intermediate Similarity	NPC25850
0.75	Intermediate Similarity	NPC21016
0.75	Intermediate Similarity	NPC276815
0.75	Intermediate Similarity	NPC324209
0.75	Intermediate Similarity	NPC146584
0.7485	Intermediate Similarity	NPC127172
0.7471	Intermediate Similarity	NPC84571
0.7469	Intermediate Similarity	NPC471906
0.7469	Intermediate Similarity	NPC244691
0.7468	Intermediate Similarity	NPC471452
0.7468	Intermediate Similarity	NPC471905
0.7468	Intermediate Similarity	NPC117609
0.7468	Intermediate Similarity	NPC290030
0.7468	Intermediate Similarity	NPC53206
0.7468	Intermediate Similarity	NPC53414
0.7455	Intermediate Similarity	NPC134293
0.7453	Intermediate Similarity	NPC314271
0.7452	Intermediate Similarity	NPC258502
0.7451	Intermediate Similarity	NPC179898
0.744	Intermediate Similarity	NPC234485
0.744	Intermediate Similarity	NPC472048
0.7436	Intermediate Similarity	NPC267205
0.7436	Intermediate Similarity	NPC193169
0.7434	Intermediate Similarity	NPC472047
0.7434	Intermediate Similarity	NPC1991
0.7427	Intermediate Similarity	NPC101207
0.7427	Intermediate Similarity	NPC311740
0.7425	Intermediate Similarity	NPC20337
0.7423	Intermediate Similarity	NPC28632
0.7421	Intermediate Similarity	NPC230811
0.7414	Intermediate Similarity	NPC232936
0.7407	Intermediate Similarity	NPC143898
0.7405	Intermediate Similarity	NPC194764
0.7405	Intermediate Similarity	NPC65005
0.7405	Intermediate Similarity	NPC264112
0.7405	Intermediate Similarity	NPC223836
0.7391	Intermediate Similarity	NPC187843
0.7386	Intermediate Similarity	NPC83572
0.7384	Intermediate Similarity	NPC314693
0.7381	Intermediate Similarity	NPC312482
0.7381	Intermediate Similarity	NPC107109
0.7378	Intermediate Similarity	NPC136878
0.7378	Intermediate Similarity	NPC476535
0.7375	Intermediate Similarity	NPC242994
0.7375	Intermediate Similarity	NPC190457
0.7375	Intermediate Similarity	NPC472903
0.7375	Intermediate Similarity	NPC138099
0.7372	Intermediate Similarity	NPC135801
0.7371	Intermediate Similarity	NPC213416
0.7368	Intermediate Similarity	NPC119224
0.7358	Intermediate Similarity	NPC170742
0.7355	Intermediate Similarity	NPC233056
0.7355	Intermediate Similarity	NPC296158
0.7342	Intermediate Similarity	NPC290803
0.7341	Intermediate Similarity	NPC101769
0.7341	Intermediate Similarity	NPC475055
0.7333	Intermediate Similarity	NPC251188
0.7333	Intermediate Similarity	NPC476821
0.7329	Intermediate Similarity	NPC181560
0.7329	Intermediate Similarity	NPC169452
0.7326	Intermediate Similarity	NPC65746
0.7325	Intermediate Similarity	NPC48036
0.7317	Intermediate Similarity	NPC471689
0.7312	Intermediate Similarity	NPC175552
0.731	Intermediate Similarity	NPC477410
0.731	Intermediate Similarity	NPC45846
0.7308	Intermediate Similarity	NPC34070
0.7308	Intermediate Similarity	NPC469526
0.7305	Intermediate Similarity	NPC474191
0.7303	Intermediate Similarity	NPC245975
0.7296	Intermediate Similarity	NPC86524
0.7296	Intermediate Similarity	NPC315275
0.7296	Intermediate Similarity	NPC191976
0.7294	Intermediate Similarity	NPC142339
0.7294	Intermediate Similarity	NPC77807
0.7294	Intermediate Similarity	NPC5379
0.7294	Intermediate Similarity	NPC14561
0.7284	Intermediate Similarity	NPC472904
0.7284	Intermediate Similarity	NPC246638
0.7284	Intermediate Similarity	NPC283292
0.7284	Intermediate Similarity	NPC305845
0.7284	Intermediate Similarity	NPC204045
0.7284	Intermediate Similarity	NPC290550
0.7283	Intermediate Similarity	NPC294965
0.7283	Intermediate Similarity	NPC470694
0.7278	Intermediate Similarity	NPC166480
0.7278	Intermediate Similarity	NPC282780
0.7278	Intermediate Similarity	NPC44437
0.7278	Intermediate Similarity	NPC474519
0.7278	Intermediate Similarity	NPC477048
0.7278	Intermediate Similarity	NPC475645
0.7278	Intermediate Similarity	NPC477047
0.7267	Intermediate Similarity	NPC471819
0.7262	Intermediate Similarity	NPC35
0.7262	Intermediate Similarity	NPC202157
0.7261	Intermediate Similarity	NPC478190
0.7256	Intermediate Similarity	NPC475813
0.7251	Intermediate Similarity	NPC178976
0.7251	Intermediate Similarity	NPC199463
0.7251	Intermediate Similarity	NPC179732
0.7251	Intermediate Similarity	NPC37543
0.7251	Intermediate Similarity	NPC236796
0.7244	Intermediate Similarity	NPC62219
0.7244	Intermediate Similarity	NPC26697
0.7241	Intermediate Similarity	NPC236132
0.7241	Intermediate Similarity	NPC476822
0.7241	Intermediate Similarity	NPC207690
0.7241	Intermediate Similarity	NPC270837
0.7239	Intermediate Similarity	NPC193555
0.7239	Intermediate Similarity	NPC135524
0.7239	Intermediate Similarity	NPC474961
0.7233	Intermediate Similarity	NPC161632
0.7229	Intermediate Similarity	NPC10842
0.7225	Intermediate Similarity	NPC278427
0.7219	Intermediate Similarity	NPC313453
0.7219	Intermediate Similarity	NPC149889
0.7219	Intermediate Similarity	NPC312338
0.7216	Intermediate Similarity	NPC107009
0.7215	Intermediate Similarity	NPC4170
0.7215	Intermediate Similarity	NPC294226
0.7215	Intermediate Similarity	NPC37299
0.7215	Intermediate Similarity	NPC180261
0.7209	Intermediate Similarity	NPC100123
0.7209	Intermediate Similarity	NPC245891
0.7209	Intermediate Similarity	NPC104876
0.7208	Intermediate Similarity	NPC231774
0.7205	Intermediate Similarity	NPC206207
0.7205	Intermediate Similarity	NPC141368
0.7202	Intermediate Similarity	NPC294646
0.7202	Intermediate Similarity	NPC476532
0.72	Intermediate Similarity	NPC26386
0.72	Intermediate Similarity	NPC102372
0.7195	Intermediate Similarity	NPC469885
0.7193	Intermediate Similarity	NPC470762
0.7193	Intermediate Similarity	NPC475799
0.7193	Intermediate Similarity	NPC13779
0.7193	Intermediate Similarity	NPC474167
0.7188	Intermediate Similarity	NPC118919
0.7186	Intermediate Similarity	NPC470479
0.7176	Intermediate Similarity	NPC93552
0.7176	Intermediate Similarity	NPC89474
0.7175	Intermediate Similarity	NPC163130
0.7175	Intermediate Similarity	NPC165979
0.7171	Intermediate Similarity	NPC66252
0.7168	Intermediate Similarity	NPC14353
0.7168	Intermediate Similarity	NPC80375
0.7168	Intermediate Similarity	NPC155302
0.7168	Intermediate Similarity	NPC228785
0.7168	Intermediate Similarity	NPC45146
0.7168	Intermediate Similarity	NPC320359
0.7168	Intermediate Similarity	NPC235018
0.7168	Intermediate Similarity	NPC56085
0.7168	Intermediate Similarity	NPC161947
0.7159	Intermediate Similarity	NPC37870
0.7152	Intermediate Similarity	NPC29932
0.7152	Intermediate Similarity	NPC17843
0.7152	Intermediate Similarity	NPC229649
0.7152	Intermediate Similarity	NPC48762
0.7152	Intermediate Similarity	NPC309430
0.7152	Intermediate Similarity	NPC193703
0.7152	Intermediate Similarity	NPC10764
0.7152	Intermediate Similarity	NPC21599
0.7151	Intermediate Similarity	NPC273843
0.7143	Intermediate Similarity	NPC245058
0.7143	Intermediate Similarity	NPC53001
0.7143	Intermediate Similarity	NPC477454
0.7135	Intermediate Similarity	NPC28042

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 NPC4331 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	255
0.1-0.2	897
0.2-0.3	1867
0.3-0.4	3184
0.4-0.5	2034
0.5-0.6	741
0.6-0.7	168
0.7-0.8	4
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
0.7628	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7372	Intermediate Similarity	NPD943	Approved
0.7091	Intermediate Similarity	NPD3300	Phase 2
0.7048	Intermediate Similarity	NPD7390	Discontinued
0.6905	Remote Similarity	NPD2532	Approved
0.6905	Remote Similarity	NPD2534	Approved
0.6905	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD2533	Approved
0.6893	Remote Similarity	NPD6232	Discontinued
0.6872	Remote Similarity	NPD7473	Discontinued
0.6868	Remote Similarity	NPD5027	Approved
0.6868	Remote Similarity	NPD5031	Approved
0.6868	Remote Similarity	NPD5029	Approved
0.6864	Remote Similarity	NPD1512	Approved
0.6862	Remote Similarity	NPD6214	Clinical (unspecified phase)
0.6862	Remote Similarity	NPD6212	Phase 3
0.6862	Remote Similarity	NPD6213	Phase 3
0.6831	Remote Similarity	NPD5032	Approved
0.6825	Remote Similarity	NPD6534	Approved
0.6825	Remote Similarity	NPD6535	Approved
0.6809	Remote Similarity	NPD5968	Phase 3
0.6807	Remote Similarity	NPD2800	Approved
0.6782	Remote Similarity	NPD2801	Approved
0.6782	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD5038	Approved
0.6774	Remote Similarity	NPD5037	Approved
0.6746	Remote Similarity	NPD1511	Approved
0.6739	Remote Similarity	NPD5028	Approved
0.6739	Remote Similarity	NPD5034	Approved
0.6739	Remote Similarity	NPD5026	Approved
0.6739	Remote Similarity	NPD4954	Approved
0.6739	Remote Similarity	NPD36	Approved
0.6739	Remote Similarity	NPD4955	Approved
0.6731	Remote Similarity	NPD9269	Phase 2
0.672	Remote Similarity	NPD5036	Approved
0.6719	Remote Similarity	NPD7700	Phase 2
0.6719	Remote Similarity	NPD7699	Phase 2
0.6709	Remote Similarity	NPD1470	Approved
0.6704	Remote Similarity	NPD5710	Approved
0.6704	Remote Similarity	NPD5711	Approved
0.6703	Remote Similarity	NPD5035	Approved
0.6685	Remote Similarity	NPD5030	Phase 2
0.6684	Remote Similarity	NPD8150	Discontinued
0.6667	Remote Similarity	NPD3299	Clinical (unspecified phase)
0.6649	Remote Similarity	NPD6782	Approved
0.6649	Remote Similarity	NPD6778	Approved
0.6649	Remote Similarity	NPD6777	Approved
0.6649	Remote Similarity	NPD6781	Approved
0.6649	Remote Similarity	NPD6780	Approved
0.6649	Remote Similarity	NPD6776	Approved
0.6649	Remote Similarity	NPD6779	Approved
0.6646	Remote Similarity	NPD6651	Approved
0.6629	Remote Similarity	NPD1934	Approved
0.661	Remote Similarity	NPD3882	Suspended
0.6593	Remote Similarity	NPD5033	Approved
0.6585	Remote Similarity	NPD230	Phase 1
0.6562	Remote Similarity	NPD258	Approved
0.6562	Remote Similarity	NPD257	Approved
0.6561	Remote Similarity	NPD1201	Approved
0.6548	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6527	Remote Similarity	NPD5406	Approved
0.6527	Remote Similarity	NPD5408	Approved
0.6527	Remote Similarity	NPD5404	Approved
0.6527	Remote Similarity	NPD5405	Approved
0.6527	Remote Similarity	NPD9570	Approved
0.6512	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6505	Remote Similarity	NPD5039	Approved
0.6495	Remote Similarity	NPD7282	Approved
0.6494	Remote Similarity	NPD405	Clinical (unspecified phase)
0.648	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.6474	Remote Similarity	NPD9268	Approved
0.6465	Remote Similarity	NPD7698	Approved
0.6465	Remote Similarity	NPD7697	Approved
0.6465	Remote Similarity	NPD7696	Phase 3
0.6464	Remote Similarity	NPD6959	Discontinued
0.6448	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6448	Remote Similarity	NPD6166	Phase 2
0.6448	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6446	Remote Similarity	NPD1607	Approved
0.6445	Remote Similarity	NPD8469	Approved
0.644	Remote Similarity	NPD6836	Approved
0.6432	Remote Similarity	NPD6020	Phase 2
0.6432	Remote Similarity	NPD7871	Phase 2
0.6432	Remote Similarity	NPD7870	Phase 2
0.6404	Remote Similarity	NPD1465	Phase 2
0.6398	Remote Similarity	NPD4956	Approved
0.6382	Remote Similarity	NPD7435	Discontinued
0.6378	Remote Similarity	NPD4975	Approved
0.6378	Remote Similarity	NPD4974	Approved
0.6374	Remote Similarity	NPD1247	Approved
0.6364	Remote Similarity	NPD8366	Approved
0.6345	Remote Similarity	NPD5609	Approved
0.6345	Remote Similarity	NPD5608	Approved
0.6344	Remote Similarity	NPD5844	Phase 1
0.6337	Remote Similarity	NPD7300	Phase 3
0.6337	Remote Similarity	NPD7302	Phase 3
0.6325	Remote Similarity	NPD826	Approved
0.6325	Remote Similarity	NPD1240	Approved
0.6325	Remote Similarity	NPD825	Approved
0.6324	Remote Similarity	NPD7801	Approved
0.6319	Remote Similarity	NPD5494	Approved
0.6319	Remote Similarity	NPD9569	Approved
0.6296	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6296	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6289	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6287	Remote Similarity	NPD274	Approved
0.6287	Remote Similarity	NPD275	Approved
0.6287	Remote Similarity	NPD6973	Clinical (unspecified phase)
0.6286	Remote Similarity	NPD7907	Approved
0.6278	Remote Similarity	NPD3817	Phase 2
0.6272	Remote Similarity	NPD1510	Phase 2
0.6269	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6268	Remote Similarity	NPD2899	Discontinued
0.6268	Remote Similarity	NPD4665	Approved
0.6268	Remote Similarity	NPD4111	Phase 1
0.6265	Remote Similarity	NPD259	Phase 1
0.6263	Remote Similarity	NPD3534	Clinical (unspecified phase)
0.6256	Remote Similarity	NPD7701	Phase 2
0.625	Remote Similarity	NPD4387	Approved
0.625	Remote Similarity	NPD4386	Approved
0.6244	Remote Similarity	NPD8491	Approved
0.6244	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6244	Remote Similarity	NPD7783	Phase 2
0.6242	Remote Similarity	NPD9536	Phase 1
0.6242	Remote Similarity	NPD9537	Phase 1
0.6238	Remote Similarity	NPD7211	Clinical (unspecified phase)
0.6236	Remote Similarity	NPD4380	Phase 2
0.6235	Remote Similarity	NPD2935	Discontinued
0.6231	Remote Similarity	NPD4914	Approved
0.6225	Remote Similarity	NPD8151	Discontinued
0.6222	Remote Similarity	NPD7819	Suspended
0.6218	Remote Similarity	NPD6835	Approved
0.6209	Remote Similarity	NPD7075	Discontinued
0.6209	Remote Similarity	NPD8155	Clinical (unspecified phase)
0.6207	Remote Similarity	NPD7584	Approved
0.6203	Remote Similarity	NPD3818	Discontinued
0.6195	Remote Similarity	NPD7874	Approved
0.6195	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.619	Remote Similarity	NPD555	Phase 2
0.619	Remote Similarity	NPD6797	Phase 2
0.6188	Remote Similarity	NPD8320	Phase 1
0.6188	Remote Similarity	NPD8319	Approved
0.6181	Remote Similarity	NPD5544	Approved
0.618	Remote Similarity	NPD3226	Approved
0.618	Remote Similarity	NPD3455	Phase 2
0.617	Remote Similarity	NPD1221	Approved
0.6169	Remote Similarity	NPD6823	Phase 2
0.6158	Remote Similarity	NPD6807	Phase 3
0.6158	Remote Similarity	NPD7251	Discontinued
0.6154	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD7283	Approved
0.6145	Remote Similarity	NPD6599	Discontinued
0.6138	Remote Similarity	NPD5190	Phase 2
0.6138	Remote Similarity	NPD7074	Phase 3
0.6136	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6135	Remote Similarity	NPD7301	Phase 3
0.6133	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6129	Remote Similarity	NPD8067	Phase 3
0.6119	Remote Similarity	NPD2494	Approved
0.6119	Remote Similarity	NPD2493	Approved
0.6105	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6105	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6105	Remote Similarity	NPD2346	Discontinued
0.6098	Remote Similarity	NPD1164	Approved
0.6087	Remote Similarity	NPD919	Approved
0.6085	Remote Similarity	NPD7054	Approved
0.6085	Remote Similarity	NPD4603	Phase 2
0.608	Remote Similarity	NPD5195	Discontinued
0.6077	Remote Similarity	NPD6801	Discontinued
0.6073	Remote Similarity	NPD7922	Phase 1
0.6069	Remote Similarity	NPD1549	Phase 2
0.6062	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.6053	Remote Similarity	NPD7472	Approved
0.6043	Remote Similarity	NPD3926	Phase 2
0.6042	Remote Similarity	NPD7808	Phase 3
0.604	Remote Similarity	NPD3450	Approved
0.604	Remote Similarity	NPD3452	Approved
0.6029	Remote Similarity	NPD4583	Approved
0.6029	Remote Similarity	NPD4582	Approved
0.6027	Remote Similarity	NPD1483	Discontinued
0.6021	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6012	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6011	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6011	Remote Similarity	NPD1220	Phase 1
0.601	Remote Similarity	NPD2491	Approved
0.601	Remote Similarity	NPD5610	Approved
0.6	Remote Similarity	NPD5543	Approved
0.6	Remote Similarity	NPD3400	Discontinued
0.6	Remote Similarity	NPD4388	Approved
0.6	Remote Similarity	NPD3750	Approved
0.6	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.599	Remote Similarity	NPD2490	Approved
0.599	Remote Similarity	NPD2488	Approved
0.5989	Remote Similarity	NPD6799	Approved
0.598	Remote Similarity	NPD4004	Approved
0.598	Remote Similarity	NPD4002	Approved
0.5976	Remote Similarity	NPD182	Clinical (unspecified phase)
0.5976	Remote Similarity	NPD9622	Approved
0.597	Remote Similarity	NPD5194	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