NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	271.12
Volume:	287.092
LogP:	1.968
LogD:	2.35
LogS:	-2.965
# Rotatable Bonds:	6
TPSA:	58.56
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.876
Synthetic Accessibility Score:	1.981
Fsp3:	0.188
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:	-4.797
MDCK Permeability:	1.0767833373392932e-05
Pgp-inhibitor:	0.048
Pgp-substrate:	0.835
Human Intestinal Absorption (HIA):	0.011
20% Bioavailability (F20%):	0.28
30% Bioavailability (F30%):	0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.496
Plasma Protein Binding (PPB):	88.46212005615234%
Volume Distribution (VD):	0.833
Pgp-substrate:	9.593257904052734%

ADMET: Metabolism

CYP1A2-inhibitor:	0.529
CYP1A2-substrate:	0.119
CYP2C19-inhibitor:	0.876
CYP2C19-substrate:	0.622
CYP2C9-inhibitor:	0.733
CYP2C9-substrate:	0.856
CYP2D6-inhibitor:	0.558
CYP2D6-substrate:	0.793
CYP3A4-inhibitor:	0.188
CYP3A4-substrate:	0.29

ADMET: Excretion

Clearance (CL):	10.159
Half-life (T1/2):	0.569

ADMET: Toxicity

hERG Blockers:	0.308
Human Hepatotoxicity (H-HT):	0.207
Drug-inuced Liver Injury (DILI):	0.173
AMES Toxicity:	0.052
Rat Oral Acute Toxicity:	0.02
Maximum Recommended Daily Dose:	0.743
Skin Sensitization:	0.183
Carcinogencity:	0.12
Eye Corrosion:	0.003
Eye Irritation:	0.095
Respiratory Toxicity:	0.054

Download Data

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

Natural Product: NPC29477

Natural Product ID:	NPC29477
*Common Name:**	(-)-Tembamide
IUPAC Name:	N-[(2S)-2-hydroxy-2-(4-methoxyphenyl)ethyl]benzamide
Synonyms:	(-)-Tembamide
Standard InCHIKey:	NICURWGAEFHESQ-OAHLLOKOSA-N
Standard InCHI:	InChI=1S/C16H17NO3/c1-20-14-9-7-12(8-10-14)15(18)11-17-16(19)13-5-3-2-4-6-13/h2-10,15,18H,11H2,1H3,(H,17,19)/t15-/m1/s1
SMILES:	COc1ccc(cc1)[C@@H](CN=C(c1ccccc1)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL453171
PubChem CID:	6482976
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002279] Benzene and substituted derivatives [CHEMONTID:0000176] Benzoic acids and derivatives [CHEMONTID:0000178] Benzamides

*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
NPO5045	Aegle marmelos	Species	Rutaceae	Eukaryota	leaves	n.a.	n.a.	PMID[18760601]
NPO5045	Aegle marmelos	Species	Rutaceae	Eukaryota	n.a.	bark	n.a.	PMID[21875114]
NPO5045	Aegle marmelos	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23434131]
NPO5045	Aegle marmelos	Species	Rutaceae	Eukaryota	n.a.	fruit	n.a.	PMID[26247834]
NPO5045	Aegle marmelos	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[30579794]
NPO5045	Aegle marmelos	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5045	Aegle marmelos	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5045	Aegle marmelos	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]

☑ 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
Others	4

Activity Type	# Activity
Others	4

Target ID	Target Type	Target Name	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified	Inhibition	=	1.5	%	PMID[495805]
NPT2	Others	Unspecified	Inhibition	=	7.8	%	PMID[495805]
NPT2	Others	Unspecified	Inhibition	=	13.5	%	PMID[495805]
NPT2	Others	Unspecified	Inhibition	=	11.4	%	PMID[495805]

☑ 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 NPC29477 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	156
0.1-0.2	1182
0.2-0.3	5871
0.3-0.4	12028
0.4-0.5	5592
0.5-0.6	11377
0.6-0.7	5657
0.7-0.8	785
0.8-0.85	35
0.85-0.9	9
0.9-0.95	2
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9748	High Similarity	NPC95733
0.9748	High Similarity	NPC62101
0.95	High Similarity	NPC211218
0.9407	High Similarity	NPC43275
0.8852	High Similarity	NPC263835
0.8712	High Similarity	NPC160607
0.8712	High Similarity	NPC204848
0.8712	High Similarity	NPC312770
0.8712	High Similarity	NPC41473
0.8712	High Similarity	NPC14600
0.8647	High Similarity	NPC299583
0.854	High Similarity	NPC313414
0.8529	High Similarity	NPC178466
0.8529	High Similarity	NPC63628
0.8443	Intermediate Similarity	NPC303370
0.8417	Intermediate Similarity	NPC166837
0.8372	Intermediate Similarity	NPC301713
0.8346	Intermediate Similarity	NPC471315
0.8346	Intermediate Similarity	NPC471314
0.832	Intermediate Similarity	NPC256369
0.8319	Intermediate Similarity	NPC153690
0.8308	Intermediate Similarity	NPC251571
0.8296	Intermediate Similarity	NPC254610
0.8258	Intermediate Similarity	NPC114102
0.8244	Intermediate Similarity	NPC155838
0.8195	Intermediate Similarity	NPC214869
0.8195	Intermediate Similarity	NPC471953
0.8189	Intermediate Similarity	NPC83279
0.8182	Intermediate Similarity	NPC195749
0.8182	Intermediate Similarity	NPC35961
0.8182	Intermediate Similarity	NPC52029
0.8167	Intermediate Similarity	NPC24101
0.8167	Intermediate Similarity	NPC96224
0.811	Intermediate Similarity	NPC289330
0.811	Intermediate Similarity	NPC471308
0.811	Intermediate Similarity	NPC160120
0.811	Intermediate Similarity	NPC17388
0.811	Intermediate Similarity	NPC321133
0.811	Intermediate Similarity	NPC53596
0.8102	Intermediate Similarity	NPC296898
0.8099	Intermediate Similarity	NPC471032
0.8099	Intermediate Similarity	NPC474272
0.8099	Intermediate Similarity	NPC470935
0.8083	Intermediate Similarity	NPC251306
0.8051	Intermediate Similarity	NPC305205
0.8043	Intermediate Similarity	NPC83289
0.8043	Intermediate Similarity	NPC189724
0.8043	Intermediate Similarity	NPC212850
0.803	Intermediate Similarity	NPC153990
0.8028	Intermediate Similarity	NPC115144
0.8028	Intermediate Similarity	NPC277857
0.8	Intermediate Similarity	NPC231705
0.8	Intermediate Similarity	NPC113457
0.7969	Intermediate Similarity	NPC41801
0.7958	Intermediate Similarity	NPC132771
0.7958	Intermediate Similarity	NPC245974
0.7951	Intermediate Similarity	NPC258056
0.7937	Intermediate Similarity	NPC82963
0.7937	Intermediate Similarity	NPC258992
0.7934	Intermediate Similarity	NPC142297
0.7917	Intermediate Similarity	NPC114659
0.7917	Intermediate Similarity	NPC182119
0.7917	Intermediate Similarity	NPC211551
0.7917	Intermediate Similarity	NPC139699
0.7914	Intermediate Similarity	NPC477838
0.7914	Intermediate Similarity	NPC477837
0.7895	Intermediate Similarity	NPC186898
0.7887	Intermediate Similarity	NPC5462
0.7886	Intermediate Similarity	NPC474149
0.7874	Intermediate Similarity	NPC323948
0.7874	Intermediate Similarity	NPC311737
0.7874	Intermediate Similarity	NPC38458
0.7869	Intermediate Similarity	NPC309982
0.7869	Intermediate Similarity	NPC146530
0.7863	Intermediate Similarity	NPC307020
0.7857	Intermediate Similarity	NPC464
0.7857	Intermediate Similarity	NPC185541
0.782	Intermediate Similarity	NPC218323
0.7817	Intermediate Similarity	NPC247298
0.7805	Intermediate Similarity	NPC290566
0.7805	Intermediate Similarity	NPC306045
0.7805	Intermediate Similarity	NPC265211
0.7805	Intermediate Similarity	NPC145638
0.7797	Intermediate Similarity	NPC100870
0.7795	Intermediate Similarity	NPC85292
0.7795	Intermediate Similarity	NPC54507
0.7795	Intermediate Similarity	NPC229147
0.7794	Intermediate Similarity	NPC93882
0.7794	Intermediate Similarity	NPC130595
0.7794	Intermediate Similarity	NPC470392
0.7778	Intermediate Similarity	NPC118202
0.7769	Intermediate Similarity	NPC8302
0.7769	Intermediate Similarity	NPC284078
0.7769	Intermediate Similarity	NPC183262
0.7769	Intermediate Similarity	NPC470393
0.7769	Intermediate Similarity	NPC154899
0.7769	Intermediate Similarity	NPC233396
0.776	Intermediate Similarity	NPC153795
0.776	Intermediate Similarity	NPC42911
0.776	Intermediate Similarity	NPC290353
0.775	Intermediate Similarity	NPC178902
0.7737	Intermediate Similarity	NPC6854
0.7737	Intermediate Similarity	NPC285078
0.7737	Intermediate Similarity	NPC313737
0.7734	Intermediate Similarity	NPC474933
0.773	Intermediate Similarity	NPC474128
0.773	Intermediate Similarity	NPC195814
0.7727	Intermediate Similarity	NPC471693
0.7724	Intermediate Similarity	NPC75440
0.7724	Intermediate Similarity	NPC201959
0.7721	Intermediate Similarity	NPC329595
0.7721	Intermediate Similarity	NPC326599
0.7717	Intermediate Similarity	NPC317254
0.7717	Intermediate Similarity	NPC10286
0.7717	Intermediate Similarity	NPC37302
0.7717	Intermediate Similarity	NPC213
0.771	Intermediate Similarity	NPC474862
0.7705	Intermediate Similarity	NPC92623
0.7705	Intermediate Similarity	NPC135464
0.7703	Intermediate Similarity	NPC10221
0.7703	Intermediate Similarity	NPC305700
0.7703	Intermediate Similarity	NPC18249
0.7703	Intermediate Similarity	NPC140915
0.7703	Intermediate Similarity	NPC187028
0.7703	Intermediate Similarity	NPC197741
0.7698	Intermediate Similarity	NPC176730
0.7698	Intermediate Similarity	NPC123175
0.7687	Intermediate Similarity	NPC127402
0.7686	Intermediate Similarity	NPC108875
0.7686	Intermediate Similarity	NPC38079
0.7681	Intermediate Similarity	NPC218530
0.7676	Intermediate Similarity	NPC100478
0.7676	Intermediate Similarity	NPC222039
0.7674	Intermediate Similarity	NPC131118
0.7669	Intermediate Similarity	NPC94276
0.7669	Intermediate Similarity	NPC109822
0.766	Intermediate Similarity	NPC77572
0.7656	Intermediate Similarity	NPC141090
0.7652	Intermediate Similarity	NPC100099
0.7652	Intermediate Similarity	NPC36016
0.7652	Intermediate Similarity	NPC150026
0.7652	Intermediate Similarity	NPC71090
0.7638	Intermediate Similarity	NPC235250
0.7638	Intermediate Similarity	NPC228287
0.7638	Intermediate Similarity	NPC180508
0.7623	Intermediate Similarity	NPC42383
0.7615	Intermediate Similarity	NPC268572
0.7612	Intermediate Similarity	NPC194519
0.7612	Intermediate Similarity	NPC81641
0.7612	Intermediate Similarity	NPC148627
0.7609	Intermediate Similarity	NPC169766
0.7603	Intermediate Similarity	NPC192596
0.7597	Intermediate Similarity	NPC476266
0.7597	Intermediate Similarity	NPC283468
0.7594	Intermediate Similarity	NPC38761
0.7594	Intermediate Similarity	NPC328267
0.7594	Intermediate Similarity	NPC474160
0.7594	Intermediate Similarity	NPC76465
0.7591	Intermediate Similarity	NPC308885
0.7591	Intermediate Similarity	NPC255550
0.7591	Intermediate Similarity	NPC45191
0.7589	Intermediate Similarity	NPC36434
0.7584	Intermediate Similarity	NPC207675
0.7584	Intermediate Similarity	NPC212699
0.7581	Intermediate Similarity	NPC97811
0.7578	Intermediate Similarity	NPC53906
0.7559	Intermediate Similarity	NPC35344
0.7559	Intermediate Similarity	NPC26524
0.7559	Intermediate Similarity	NPC141003
0.7556	Intermediate Similarity	NPC191037
0.7556	Intermediate Similarity	NPC276212
0.7556	Intermediate Similarity	NPC58607
0.7556	Intermediate Similarity	NPC178284
0.7541	Intermediate Similarity	NPC12987
0.7541	Intermediate Similarity	NPC474603
0.7538	Intermediate Similarity	NPC474214
0.7538	Intermediate Similarity	NPC5932
0.7538	Intermediate Similarity	NPC122009
0.7537	Intermediate Similarity	NPC86502
0.7537	Intermediate Similarity	NPC106914
0.7537	Intermediate Similarity	NPC134195
0.7537	Intermediate Similarity	NPC197351
0.7537	Intermediate Similarity	NPC246648
0.7537	Intermediate Similarity	NPC114901
0.7537	Intermediate Similarity	NPC293701
0.7537	Intermediate Similarity	NPC48990
0.7536	Intermediate Similarity	NPC274732
0.7536	Intermediate Similarity	NPC97870
0.7536	Intermediate Similarity	NPC247018
0.7536	Intermediate Similarity	NPC307123
0.7535	Intermediate Similarity	NPC298821
0.7533	Intermediate Similarity	NPC107602
0.7521	Intermediate Similarity	NPC51633
0.7519	Intermediate Similarity	NPC301651
0.7519	Intermediate Similarity	NPC473556
0.7518	Intermediate Similarity	NPC471316
0.7518	Intermediate Similarity	NPC470706
0.7517	Intermediate Similarity	NPC275027
0.7516	Intermediate Similarity	NPC179250
0.7516	Intermediate Similarity	NPC50380

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 NPC29477 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	126
0.1-0.2	644
0.2-0.3	1083
0.3-0.4	1858
0.4-0.5	2634
0.5-0.6	1771
0.6-0.7	815
0.7-0.8	214
0.8-0.85	5
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8284	Intermediate Similarity	NPD3054	Approved
0.8284	Intermediate Similarity	NPD3052	Approved
0.8281	Intermediate Similarity	NPD3676	Clinical (unspecified phase)
0.8156	Intermediate Similarity	NPD4123	Phase 3
0.814	Intermediate Similarity	NPD1669	Approved
0.811	Intermediate Similarity	NPD2668	Approved
0.811	Intermediate Similarity	NPD2667	Approved
0.8	Intermediate Similarity	NPD3685	Discontinued
0.8	Intermediate Similarity	NPD6583	Phase 3
0.8	Intermediate Similarity	NPD6582	Phase 2
0.7985	Intermediate Similarity	NPD3056	Clinical (unspecified phase)
0.7931	Intermediate Similarity	NPD4005	Discontinued
0.7929	Intermediate Similarity	NPD3060	Approved
0.7926	Intermediate Similarity	NPD7477	Discontinued
0.7923	Intermediate Similarity	NPD2561	Approved
0.7923	Intermediate Similarity	NPD2562	Approved
0.7903	Intermediate Similarity	NPD821	Approved
0.7895	Intermediate Similarity	NPD4993	Discontinued
0.7883	Intermediate Similarity	NPD1772	Clinical (unspecified phase)
0.7877	Intermediate Similarity	NPD4675	Approved
0.7877	Intermediate Similarity	NPD4678	Approved
0.7868	Intermediate Similarity	NPD2238	Phase 2
0.7863	Intermediate Similarity	NPD4659	Approved
0.7829	Intermediate Similarity	NPD5238	Clinical (unspecified phase)
0.7826	Intermediate Similarity	NPD3552	Approved
0.7826	Intermediate Similarity	NPD3555	Approved
0.7826	Intermediate Similarity	NPD3553	Approved
0.7826	Intermediate Similarity	NPD3554	Approved
0.782	Intermediate Similarity	NPD6584	Phase 3
0.7805	Intermediate Similarity	NPD9380	Clinical (unspecified phase)
0.7795	Intermediate Similarity	NPD3596	Phase 2
0.7794	Intermediate Similarity	NPD2674	Phase 3
0.7794	Intermediate Similarity	NPD839	Approved
0.7794	Intermediate Similarity	NPD840	Approved
0.7793	Intermediate Similarity	NPD7131	Phase 3
0.7786	Intermediate Similarity	NPD2235	Phase 2
0.7786	Intermediate Similarity	NPD2231	Phase 2
0.7746	Intermediate Similarity	NPD6331	Phase 2
0.7744	Intermediate Similarity	NPD4104	Clinical (unspecified phase)
0.7744	Intermediate Similarity	NPD3567	Approved
0.7744	Intermediate Similarity	NPD4103	Phase 2
0.7744	Intermediate Similarity	NPD3568	Approved
0.7737	Intermediate Similarity	NPD5837	Clinical (unspecified phase)
0.7734	Intermediate Similarity	NPD16	Approved
0.7734	Intermediate Similarity	NPD856	Approved
0.7724	Intermediate Similarity	NPD5261	Clinical (unspecified phase)
0.7676	Intermediate Similarity	NPD4236	Phase 3
0.7676	Intermediate Similarity	NPD4237	Approved
0.7674	Intermediate Similarity	NPD6580	Approved
0.7674	Intermediate Similarity	NPD6581	Approved
0.7669	Intermediate Similarity	NPD7258	Clinical (unspecified phase)
0.7655	Intermediate Similarity	NPD3536	Discontinued
0.7652	Intermediate Similarity	NPD2232	Approved
0.7652	Intermediate Similarity	NPD2233	Approved
0.7652	Intermediate Similarity	NPD2230	Approved
0.7634	Intermediate Similarity	NPD3421	Phase 3
0.7622	Intermediate Similarity	NPD6658	Clinical (unspecified phase)
0.7615	Intermediate Similarity	NPD6830	Clinical (unspecified phase)
0.7606	Intermediate Similarity	NPD7596	Clinical (unspecified phase)
0.76	Intermediate Similarity	NPD5773	Approved
0.76	Intermediate Similarity	NPD5772	Approved
0.7597	Intermediate Similarity	NPD318	Approved
0.7597	Intermediate Similarity	NPD317	Approved
0.7594	Intermediate Similarity	NPD2429	Approved
0.7594	Intermediate Similarity	NPD4129	Approved
0.7594	Intermediate Similarity	NPD2428	Approved
0.7591	Intermediate Similarity	NPD1048	Approved
0.7591	Intermediate Similarity	NPD3145	Approved
0.7591	Intermediate Similarity	NPD3144	Approved
0.7589	Intermediate Similarity	NPD2161	Phase 2
0.7586	Intermediate Similarity	NPD7213	Phase 3
0.7586	Intermediate Similarity	NPD7212	Phase 2
0.7578	Intermediate Similarity	NPD2557	Approved
0.7569	Intermediate Similarity	NPD5241	Discontinued
0.7569	Intermediate Similarity	NPD3692	Discontinued
0.7568	Intermediate Similarity	NPD6523	Clinical (unspecified phase)
0.7566	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7557	Intermediate Similarity	NPD2556	Approved
0.7557	Intermediate Similarity	NPD2554	Approved
0.7552	Intermediate Similarity	NPD2458	Approved
0.7552	Intermediate Similarity	NPD2976	Clinical (unspecified phase)
0.7552	Intermediate Similarity	NPD2460	Phase 3
0.7552	Intermediate Similarity	NPD2459	Approved
0.7537	Intermediate Similarity	NPD2922	Phase 1
0.7536	Intermediate Similarity	NPD1423	Approved
0.7518	Intermediate Similarity	NPD3179	Approved
0.7518	Intermediate Similarity	NPD3180	Approved
0.7517	Intermediate Similarity	NPD6667	Approved
0.7517	Intermediate Similarity	NPD6666	Approved
0.75	Intermediate Similarity	NPD2157	Approved
0.75	Intermediate Similarity	NPD1712	Approved
0.7483	Intermediate Similarity	NPD7153	Discontinued
0.7482	Intermediate Similarity	NPD1558	Phase 1
0.7481	Intermediate Similarity	NPD2594	Approved
0.7481	Intermediate Similarity	NPD2595	Approved
0.7467	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7467	Intermediate Similarity	NPD6072	Discontinued
0.7464	Intermediate Similarity	NPD3374	Clinical (unspecified phase)
0.7445	Intermediate Similarity	NPD596	Approved
0.7445	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7445	Intermediate Similarity	NPD600	Approved
0.744	Intermediate Similarity	NPD2684	Approved
0.7434	Intermediate Similarity	NPD3560	Approved
0.7434	Intermediate Similarity	NPD3556	Approved
0.7434	Intermediate Similarity	NPD3558	Approved
0.7434	Intermediate Similarity	NPD3559	Clinical (unspecified phase)
0.7434	Intermediate Similarity	NPD3557	Approved
0.7432	Intermediate Similarity	NPD2122	Discontinued
0.7431	Intermediate Similarity	NPD4162	Approved
0.7426	Intermediate Similarity	NPD7451	Discontinued
0.7422	Intermediate Similarity	NPD2234	Approved
0.7422	Intermediate Similarity	NPD2229	Approved
0.7422	Intermediate Similarity	NPD2228	Approved
0.7415	Intermediate Similarity	NPD7447	Phase 1
0.7415	Intermediate Similarity	NPD3985	Discontinued
0.7413	Intermediate Similarity	NPD1375	Discontinued
0.741	Intermediate Similarity	NPD3058	Clinical (unspecified phase)
0.741	Intermediate Similarity	NPD6407	Approved
0.741	Intermediate Similarity	NPD6405	Approved
0.7405	Intermediate Similarity	NPD1548	Phase 1
0.7405	Intermediate Similarity	NPD2486	Discontinued
0.74	Intermediate Similarity	NPD6502	Phase 2
0.7394	Intermediate Similarity	NPD4108	Discontinued
0.7391	Intermediate Similarity	NPD6179	Discontinued
0.7391	Intermediate Similarity	NPD1024	Discontinued
0.7391	Intermediate Similarity	NPD5163	Phase 2
0.7391	Intermediate Similarity	NPD3027	Phase 3
0.7368	Intermediate Similarity	NPD3847	Discontinued
0.7368	Intermediate Similarity	NPD6818	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD7089	Clinical (unspecified phase)
0.7361	Intermediate Similarity	NPD4149	Clinical (unspecified phase)
0.7353	Intermediate Similarity	NPD1817	Approved
0.7353	Intermediate Similarity	NPD1820	Approved
0.7353	Intermediate Similarity	NPD1819	Approved
0.7353	Intermediate Similarity	NPD1818	Approved
0.7351	Intermediate Similarity	NPD3796	Clinical (unspecified phase)
0.7348	Intermediate Similarity	NPD6382	Discontinued
0.7348	Intermediate Similarity	NPD3049	Approved
0.7343	Intermediate Similarity	NPD3175	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD6543	Approved
0.7333	Intermediate Similarity	NPD6542	Approved
0.7333	Intermediate Similarity	NPD6540	Phase 3
0.7333	Intermediate Similarity	NPD6539	Approved
0.7311	Intermediate Similarity	NPD2934	Approved
0.7311	Intermediate Similarity	NPD2933	Approved
0.731	Intermediate Similarity	NPD5177	Phase 3
0.7308	Intermediate Similarity	NPD709	Approved
0.7299	Intermediate Similarity	NPD3691	Phase 2
0.7299	Intermediate Similarity	NPD3690	Phase 2
0.7299	Intermediate Similarity	NPD7018	Phase 2
0.7299	Intermediate Similarity	NPD558	Phase 2
0.7297	Intermediate Similarity	NPD2874	Phase 2
0.7292	Intermediate Similarity	NPD5865	Clinical (unspecified phase)
0.7292	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7286	Intermediate Similarity	NPD5745	Approved
0.728	Intermediate Similarity	NPD968	Approved
0.7279	Intermediate Similarity	NPD6538	Approved
0.7279	Intermediate Similarity	NPD6815	Approved
0.7279	Intermediate Similarity	NPD6541	Approved
0.7273	Intermediate Similarity	NPD6380	Phase 1
0.7273	Intermediate Similarity	NPD3846	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD7773	Phase 2
0.7267	Intermediate Similarity	NPD3687	Approved
0.7267	Intermediate Similarity	NPD3686	Approved
0.7266	Intermediate Similarity	NPD3164	Approved
0.7266	Intermediate Similarity	NPD3136	Phase 2
0.7266	Intermediate Similarity	NPD3165	Approved
0.7266	Intermediate Similarity	NPD3167	Approved
0.7266	Intermediate Similarity	NPD3166	Approved
0.7255	Intermediate Similarity	NPD2977	Approved
0.7255	Intermediate Similarity	NPD7046	Clinical (unspecified phase)
0.7255	Intermediate Similarity	NPD2978	Approved
0.7254	Intermediate Similarity	NPD4097	Suspended
0.7254	Intermediate Similarity	NPD2568	Approved
0.7254	Intermediate Similarity	NPD4579	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD2859	Approved
0.725	Intermediate Similarity	NPD2860	Approved
0.7248	Intermediate Similarity	NPD7527	Clinical (unspecified phase)
0.7248	Intermediate Similarity	NPD52	Approved
0.7248	Intermediate Similarity	NPD7526	Approved
0.7246	Intermediate Similarity	NPD2861	Phase 2
0.7244	Intermediate Similarity	NPD6746	Phase 2
0.7244	Intermediate Similarity	NPD5451	Approved
0.7239	Intermediate Similarity	NPD3294	Phase 2
0.7234	Intermediate Similarity	NPD3061	Approved
0.7234	Intermediate Similarity	NPD3062	Approved
0.7234	Intermediate Similarity	NPD3597	Clinical (unspecified phase)
0.7234	Intermediate Similarity	NPD3059	Approved
0.7231	Intermediate Similarity	NPD595	Approved
0.7231	Intermediate Similarity	NPD593	Approved
0.723	Intermediate Similarity	NPD4357	Discontinued
0.7226	Intermediate Similarity	NPD1135	Approved
0.7226	Intermediate Similarity	NPD1129	Approved
0.7226	Intermediate Similarity	NPD1131	Approved
0.7226	Intermediate Similarity	NPD5604	Discontinued
0.7226	Intermediate Similarity	NPD1133	Approved
0.7226	Intermediate Similarity	NPD1134	Approved
0.7226	Intermediate Similarity	NPD4098	Discontinued
0.7222	Intermediate Similarity	NPD1725	Approved
0.7218	Intermediate Similarity	NPD3443	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