NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	250.08
Volume:	252.98
LogP:	2.64
LogD:	1.803
LogS:	-3.406
# Rotatable Bonds:	4
TPSA:	83.83
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	1
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.371
Synthetic Accessibility Score:	2.438
Fsp3:	0.231
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	2

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.656
MDCK Permeability:	1.6429661627626047e-05
Pgp-inhibitor:	0.006
Pgp-substrate:	0.005
Human Intestinal Absorption (HIA):	0.019
20% Bioavailability (F20%):	0.006
30% Bioavailability (F30%):	0.221

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.251
Plasma Protein Binding (PPB):	95.08251190185547%
Volume Distribution (VD):	0.597
Pgp-substrate:	4.084797382354736%

ADMET: Metabolism

CYP1A2-inhibitor:	0.957
CYP1A2-substrate:	0.837
CYP2C19-inhibitor:	0.323
CYP2C19-substrate:	0.099
CYP2C9-inhibitor:	0.617
CYP2C9-substrate:	0.636
CYP2D6-inhibitor:	0.589
CYP2D6-substrate:	0.304
CYP3A4-inhibitor:	0.337
CYP3A4-substrate:	0.189

ADMET: Excretion

Clearance (CL):	11.326
Half-life (T1/2):	0.929

ADMET: Toxicity

hERG Blockers:	0.015
Human Hepatotoxicity (H-HT):	0.131
Drug-inuced Liver Injury (DILI):	0.412
AMES Toxicity:	0.119
Rat Oral Acute Toxicity:	0.089
Maximum Recommended Daily Dose:	0.823
Skin Sensitization:	0.799
Carcinogencity:	0.493
Eye Corrosion:	0.027
Eye Irritation:	0.932
Respiratory Toxicity:	0.526

Download Data

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

Natural Product: NPC112135

Natural Product ID:	NPC112135
*Common Name:**	Lanceaefolic Acid Methyl Ester
IUPAC Name:	methyl 3,4-dihydroxy-5-(3-methylbut-2-enoyl)benzoate
Synonyms:	Lanceaefolic Acid Methyl Ester
Standard InCHIKey:	KPPDNWSCOKXHFG-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C13H14O5/c1-7(2)4-10(14)9-5-8(13(17)18-3)6-11(15)12(9)16/h4-6,15-16H,1-3H3
SMILES:	CC(=CC(=O)c1cc(cc(c1O)O)C(=O)OC)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL499359
PubChem CID:	10354719
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002279] Benzene and substituted derivatives [CHEMONTID:0000176] Benzoic acids and derivatives [CHEMONTID:0001350] Benzoic acid esters [CHEMONTID:0004701] p-Hydroxybenzoic acid esters [CHEMONTID:0004702] p-Hydroxybenzoic acid alkyl esters

*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
NPO31438	Piper lanceaefolium	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11809068]
NPO31438	Piper lanceaefolium	Species	Piperaceae	Eukaryota	n.a.	leaf	n.a.	PMID[11809068]

☑ 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
MIC	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20	Organism	Candida albicans	Candida albicans	MIC	=	100.0	ug.mL-1	PMID[480993]

☑ 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 NPC112135 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	340
0.1-0.2	1581
0.2-0.3	4054
0.3-0.4	9034
0.4-0.5	9414
0.5-0.6	4032
0.6-0.7	6810
0.7-0.8	6871
0.8-0.85	517
0.85-0.9	41
0.9-0.95	1
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.947	High Similarity	NPC239855
0.9259	High Similarity	NPC475111
0.9015	High Similarity	NPC158654
0.8921	High Similarity	NPC471819
0.8881	High Similarity	NPC226855
0.8841	High Similarity	NPC326847
0.875	High Similarity	NPC264145
0.8732	High Similarity	NPC314271
0.8723	High Similarity	NPC327187
0.8696	High Similarity	NPC204582
0.8681	High Similarity	NPC258856
0.8681	High Similarity	NPC75295
0.8623	High Similarity	NPC159418
0.8623	High Similarity	NPC156124
0.8623	High Similarity	NPC304929
0.8623	High Similarity	NPC283823
0.8623	High Similarity	NPC1321
0.8613	High Similarity	NPC473777
0.8611	High Similarity	NPC113397
0.8603	High Similarity	NPC94810
0.8571	High Similarity	NPC156892
0.8571	High Similarity	NPC156307
0.8551	High Similarity	NPC111888
0.8542	High Similarity	NPC50954
0.8542	High Similarity	NPC287722
0.8533	High Similarity	NPC38898
0.8529	High Similarity	NPC473744
0.8519	High Similarity	NPC473751
0.85	High Similarity	NPC204257
0.85	High Similarity	NPC176102
0.85	High Similarity	NPC267539
0.85	High Similarity	NPC72918
0.85	High Similarity	NPC71108
0.85	High Similarity	NPC254832
0.85	High Similarity	NPC18646
0.85	High Similarity	NPC29317
0.85	High Similarity	NPC229638
0.8496	Intermediate Similarity	NPC67300
0.8489	Intermediate Similarity	NPC289572
0.8489	Intermediate Similarity	NPC157478
0.8489	Intermediate Similarity	NPC295406
0.8489	Intermediate Similarity	NPC200422
0.8462	Intermediate Similarity	NPC187690
0.8462	Intermediate Similarity	NPC50823
0.8451	Intermediate Similarity	NPC221104
0.844	Intermediate Similarity	NPC158481
0.8411	Intermediate Similarity	NPC471456
0.8406	Intermediate Similarity	NPC285776
0.8403	Intermediate Similarity	NPC470842
0.8392	Intermediate Similarity	NPC275356
0.8392	Intermediate Similarity	NPC92655
0.8389	Intermediate Similarity	NPC472279
0.838	Intermediate Similarity	NPC194579
0.838	Intermediate Similarity	NPC25305
0.838	Intermediate Similarity	NPC125417
0.838	Intermediate Similarity	NPC95679
0.838	Intermediate Similarity	NPC112068
0.838	Intermediate Similarity	NPC110899
0.8378	Intermediate Similarity	NPC471907
0.8378	Intermediate Similarity	NPC238279
0.8378	Intermediate Similarity	NPC203077
0.8378	Intermediate Similarity	NPC287395
0.8378	Intermediate Similarity	NPC183655
0.8378	Intermediate Similarity	NPC166036
0.837	Intermediate Similarity	NPC184219
0.8367	Intermediate Similarity	NPC138978
0.8356	Intermediate Similarity	NPC275278
0.8356	Intermediate Similarity	NPC213900
0.8356	Intermediate Similarity	NPC105213
0.8345	Intermediate Similarity	NPC219892
0.8345	Intermediate Similarity	NPC301178
0.8345	Intermediate Similarity	NPC189823
0.8345	Intermediate Similarity	NPC284556
0.8345	Intermediate Similarity	NPC322112
0.8344	Intermediate Similarity	NPC192189
0.8333	Intermediate Similarity	NPC156654
0.8333	Intermediate Similarity	NPC99441
0.8333	Intermediate Similarity	NPC227485
0.8333	Intermediate Similarity	NPC302783
0.8333	Intermediate Similarity	NPC124842
0.8333	Intermediate Similarity	NPC473201
0.8322	Intermediate Similarity	NPC61398
0.8322	Intermediate Similarity	NPC171916
0.8322	Intermediate Similarity	NPC416
0.8322	Intermediate Similarity	NPC38545
0.8322	Intermediate Similarity	NPC325625
0.8322	Intermediate Similarity	NPC142654
0.8321	Intermediate Similarity	NPC214620
0.8311	Intermediate Similarity	NPC53362
0.8311	Intermediate Similarity	NPC476463
0.8311	Intermediate Similarity	NPC166583
0.831	Intermediate Similarity	NPC324929
0.831	Intermediate Similarity	NPC291454
0.831	Intermediate Similarity	NPC65005
0.831	Intermediate Similarity	NPC194764
0.831	Intermediate Similarity	NPC264112
0.831	Intermediate Similarity	NPC471690
0.8289	Intermediate Similarity	NPC134287
0.8289	Intermediate Similarity	NPC113906
0.8289	Intermediate Similarity	NPC79998
0.8289	Intermediate Similarity	NPC130589
0.8289	Intermediate Similarity	NPC39184
0.8288	Intermediate Similarity	NPC471417
0.8288	Intermediate Similarity	NPC66593
0.8288	Intermediate Similarity	NPC258307
0.8288	Intermediate Similarity	NPC469615
0.8286	Intermediate Similarity	NPC50763
0.8286	Intermediate Similarity	NPC302844
0.8286	Intermediate Similarity	NPC135801
0.8278	Intermediate Similarity	NPC323626
0.8278	Intermediate Similarity	NPC324233
0.8276	Intermediate Similarity	NPC478217
0.8276	Intermediate Similarity	NPC84273
0.8276	Intermediate Similarity	NPC37530
0.8276	Intermediate Similarity	NPC472035
0.8276	Intermediate Similarity	NPC313123
0.8276	Intermediate Similarity	NPC478201
0.8273	Intermediate Similarity	NPC117609
0.8267	Intermediate Similarity	NPC31132
0.8267	Intermediate Similarity	NPC96501
0.8267	Intermediate Similarity	NPC10467
0.8264	Intermediate Similarity	NPC26924
0.8264	Intermediate Similarity	NPC4796
0.8264	Intermediate Similarity	NPC473988
0.8264	Intermediate Similarity	NPC134969
0.8258	Intermediate Similarity	NPC258331
0.8255	Intermediate Similarity	NPC218490
0.8255	Intermediate Similarity	NPC153417
0.8248	Intermediate Similarity	NPC95309
0.8247	Intermediate Similarity	NPC45846
0.8243	Intermediate Similarity	NPC32058
0.8243	Intermediate Similarity	NPC85734
0.8243	Intermediate Similarity	NPC226987
0.8243	Intermediate Similarity	NPC229264
0.8243	Intermediate Similarity	NPC260946
0.8243	Intermediate Similarity	NPC143903
0.8239	Intermediate Similarity	NPC139519
0.8239	Intermediate Similarity	NPC208760
0.8231	Intermediate Similarity	NPC210966
0.8231	Intermediate Similarity	NPC142165
0.8231	Intermediate Similarity	NPC478203
0.8231	Intermediate Similarity	NPC38065
0.8231	Intermediate Similarity	NPC242893
0.8231	Intermediate Similarity	NPC126882
0.8231	Intermediate Similarity	NPC257025
0.8231	Intermediate Similarity	NPC469683
0.8227	Intermediate Similarity	NPC48036
0.8227	Intermediate Similarity	NPC153783
0.8224	Intermediate Similarity	NPC107109
0.8224	Intermediate Similarity	NPC62051
0.8224	Intermediate Similarity	NPC281477
0.8219	Intermediate Similarity	NPC11314
0.8219	Intermediate Similarity	NPC299154
0.8219	Intermediate Similarity	NPC82913
0.8217	Intermediate Similarity	NPC471788
0.8214	Intermediate Similarity	NPC34070
0.8214	Intermediate Similarity	NPC469526
0.8212	Intermediate Similarity	NPC19980
0.8212	Intermediate Similarity	NPC221249
0.8212	Intermediate Similarity	NPC256406
0.8212	Intermediate Similarity	NPC45291
0.8212	Intermediate Similarity	NPC204350
0.8207	Intermediate Similarity	NPC168471
0.8207	Intermediate Similarity	NPC326065
0.8207	Intermediate Similarity	NPC315578
0.8207	Intermediate Similarity	NPC165172
0.8207	Intermediate Similarity	NPC290664
0.8207	Intermediate Similarity	NPC64664
0.82	Intermediate Similarity	NPC102003
0.82	Intermediate Similarity	NPC198927
0.82	Intermediate Similarity	NPC264550
0.82	Intermediate Similarity	NPC142876
0.82	Intermediate Similarity	NPC139293
0.82	Intermediate Similarity	NPC40290
0.82	Intermediate Similarity	NPC92722
0.82	Intermediate Similarity	NPC333691
0.82	Intermediate Similarity	NPC264289
0.82	Intermediate Similarity	NPC69430
0.82	Intermediate Similarity	NPC195763
0.82	Intermediate Similarity	NPC200060
0.8194	Intermediate Similarity	NPC197666
0.8194	Intermediate Similarity	NPC239943
0.8194	Intermediate Similarity	NPC126739
0.8194	Intermediate Similarity	NPC191835
0.8188	Intermediate Similarity	NPC32163
0.8188	Intermediate Similarity	NPC61871
0.8188	Intermediate Similarity	NPC281020
0.8188	Intermediate Similarity	NPC119767
0.8188	Intermediate Similarity	NPC188074
0.8188	Intermediate Similarity	NPC30647
0.8188	Intermediate Similarity	NPC55557
0.8188	Intermediate Similarity	NPC125449
0.8188	Intermediate Similarity	NPC251188
0.8188	Intermediate Similarity	NPC16651
0.8182	Intermediate Similarity	NPC35598
0.8182	Intermediate Similarity	NPC150919
0.8182	Intermediate Similarity	NPC262286
0.8182	Intermediate Similarity	NPC36852
0.8182	Intermediate Similarity	NPC167098
0.8182	Intermediate Similarity	NPC296044

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 NPC112135 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	302
0.1-0.2	987
0.2-0.3	1856
0.3-0.4	2701
0.4-0.5	1796
0.5-0.6	1027
0.6-0.7	359
0.7-0.8	117
0.8-0.85	4
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8623	High Similarity	NPD230	Phase 1
0.8286	Intermediate Similarity	NPD943	Approved
0.8105	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8088	Intermediate Similarity	NPD9269	Phase 2
0.8056	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD2935	Discontinued
0.7987	Intermediate Similarity	NPD1511	Approved
0.7985	Intermediate Similarity	NPD9545	Approved
0.7922	Intermediate Similarity	NPD1934	Approved
0.7891	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7881	Intermediate Similarity	NPD1512	Approved
0.7871	Intermediate Similarity	NPD2801	Approved
0.7862	Intermediate Similarity	NPD6232	Discontinued
0.7847	Intermediate Similarity	NPD447	Suspended
0.7843	Intermediate Similarity	NPD3226	Approved
0.7838	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7836	Intermediate Similarity	NPD9493	Approved
0.7826	Intermediate Similarity	NPD7473	Discontinued
0.7815	Intermediate Similarity	NPD2533	Approved
0.7815	Intermediate Similarity	NPD2534	Approved
0.7815	Intermediate Similarity	NPD2532	Approved
0.7801	Intermediate Similarity	NPD9494	Approved
0.7794	Intermediate Similarity	NPD9268	Approved
0.7778	Intermediate Similarity	NPD1240	Approved
0.7771	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7771	Intermediate Similarity	NPD3882	Suspended
0.7687	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7687	Intermediate Similarity	NPD1510	Phase 2
0.7671	Intermediate Similarity	NPD1607	Approved
0.7628	Intermediate Similarity	NPD7411	Suspended
0.761	Intermediate Similarity	NPD7075	Discontinued
0.7595	Intermediate Similarity	NPD3817	Phase 2
0.7582	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7582	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7568	Intermediate Similarity	NPD2799	Discontinued
0.7564	Intermediate Similarity	NPD4380	Phase 2
0.7561	Intermediate Similarity	NPD3818	Discontinued
0.7535	Intermediate Similarity	NPD1470	Approved
0.7532	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7532	Intermediate Similarity	NPD1465	Phase 2
0.7532	Intermediate Similarity	NPD7819	Suspended
0.7517	Intermediate Similarity	NPD2313	Discontinued
0.75	Intermediate Similarity	NPD6190	Approved
0.7485	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7469	Intermediate Similarity	NPD1247	Approved
0.7467	Intermediate Similarity	NPD2346	Discontinued
0.7453	Intermediate Similarity	NPD919	Approved
0.7439	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7439	Intermediate Similarity	NPD6166	Phase 2
0.7439	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7434	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7424	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7417	Intermediate Similarity	NPD1549	Phase 2
0.7413	Intermediate Similarity	NPD1164	Approved
0.7403	Intermediate Similarity	NPD6799	Approved
0.7397	Intermediate Similarity	NPD3764	Approved
0.7376	Intermediate Similarity	NPD1201	Approved
0.7372	Intermediate Similarity	NPD920	Approved
0.7368	Intermediate Similarity	NPD1243	Approved
0.7368	Intermediate Similarity	NPD2800	Approved
0.7365	Intermediate Similarity	NPD7074	Phase 3
0.7358	Intermediate Similarity	NPD6801	Discontinued
0.7351	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7351	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7337	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7324	Intermediate Similarity	NPD9717	Approved
0.7321	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.732	Intermediate Similarity	NPD4628	Phase 3
0.732	Intermediate Similarity	NPD8166	Discontinued
0.7319	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7305	Intermediate Similarity	NPD7054	Approved
0.7301	Intermediate Similarity	NPD5494	Approved
0.729	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7286	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7285	Intermediate Similarity	NPD5408	Approved
0.7285	Intermediate Similarity	NPD5404	Approved
0.7285	Intermediate Similarity	NPD5405	Approved
0.7285	Intermediate Similarity	NPD5406	Approved
0.7267	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7262	Intermediate Similarity	NPD7472	Approved
0.7244	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7244	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7239	Intermediate Similarity	NPD74	Approved
0.7239	Intermediate Similarity	NPD9266	Approved
0.7237	Intermediate Similarity	NPD2344	Approved
0.7233	Intermediate Similarity	NPD6599	Discontinued
0.7219	Intermediate Similarity	NPD6797	Phase 2
0.7202	Intermediate Similarity	NPD5844	Phase 1
0.72	Intermediate Similarity	NPD6651	Approved
0.7179	Intermediate Similarity	NPD7390	Discontinued
0.7178	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD7251	Discontinued
0.7172	Intermediate Similarity	NPD1203	Approved
0.7171	Intermediate Similarity	NPD1551	Phase 2
0.7168	Intermediate Similarity	NPD8150	Discontinued
0.7164	Intermediate Similarity	NPD9267	Approved
0.7164	Intermediate Similarity	NPD9264	Approved
0.7164	Intermediate Similarity	NPD9263	Approved
0.7162	Intermediate Similarity	NPD411	Approved
0.7153	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7117	Intermediate Similarity	NPD7768	Phase 2
0.7115	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7108	Intermediate Similarity	NPD5711	Approved
0.7108	Intermediate Similarity	NPD5710	Approved
0.7097	Intermediate Similarity	NPD3750	Approved
0.7083	Intermediate Similarity	NPD1608	Approved
0.7076	Intermediate Similarity	NPD6559	Discontinued
0.7073	Intermediate Similarity	NPD3749	Approved
0.7063	Intermediate Similarity	NPD3455	Phase 2
0.7063	Intermediate Similarity	NPD7458	Discontinued
0.7059	Intermediate Similarity	NPD2796	Approved
0.7055	Intermediate Similarity	NPD5402	Approved
0.7051	Intermediate Similarity	NPD2309	Approved
0.7048	Intermediate Similarity	NPD6959	Discontinued
0.7035	Intermediate Similarity	NPD7808	Phase 3
0.7018	Intermediate Similarity	NPD5953	Discontinued
0.7013	Intermediate Similarity	NPD7266	Discontinued
0.7011	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7007	Intermediate Similarity	NPD257	Approved
0.7007	Intermediate Similarity	NPD258	Approved
0.7007	Intermediate Similarity	NPD2798	Approved
0.7006	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD7286	Phase 2
0.7	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.6993	Remote Similarity	NPD4626	Approved
0.6986	Remote Similarity	NPD1283	Approved
0.6975	Remote Similarity	NPD6386	Approved
0.6975	Remote Similarity	NPD6385	Approved
0.6957	Remote Similarity	NPD228	Approved
0.6954	Remote Similarity	NPD826	Approved
0.6954	Remote Similarity	NPD825	Approved
0.6948	Remote Similarity	NPD9570	Approved
0.6929	Remote Similarity	NPD9281	Approved
0.6928	Remote Similarity	NPD6234	Discontinued
0.6908	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6908	Remote Similarity	NPD1933	Approved
0.6903	Remote Similarity	NPD1471	Phase 3
0.6903	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6899	Remote Similarity	NPD3300	Phase 2
0.6897	Remote Similarity	NPD8312	Approved
0.6897	Remote Similarity	NPD8313	Approved
0.6892	Remote Similarity	NPD1019	Discontinued
0.6887	Remote Similarity	NPD259	Phase 1
0.6879	Remote Similarity	NPD7685	Pre-registration
0.6879	Remote Similarity	NPD7003	Approved
0.6879	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD17	Approved
0.6866	Remote Similarity	NPD9261	Approved
0.6864	Remote Similarity	NPD3926	Phase 2
0.6846	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6832	Remote Similarity	NPD5403	Approved
0.6829	Remote Similarity	NPD37	Approved
0.6821	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6821	Remote Similarity	NPD3268	Approved
0.6813	Remote Similarity	NPD5401	Approved
0.68	Remote Similarity	NPD6832	Phase 2
0.68	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6797	Remote Similarity	NPD555	Phase 2
0.6781	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6781	Remote Similarity	NPD1281	Approved
0.678	Remote Similarity	NPD8434	Phase 2
0.6774	Remote Similarity	NPD3748	Approved
0.6759	Remote Similarity	NPD1778	Approved
0.6755	Remote Similarity	NPD3027	Phase 3
0.6748	Remote Similarity	NPD824	Approved
0.6747	Remote Similarity	NPD5353	Approved
0.6739	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.6735	Remote Similarity	NPD3972	Approved
0.6733	Remote Similarity	NPD9569	Approved
0.6732	Remote Similarity	NPD4060	Phase 1
0.6732	Remote Similarity	NPD1613	Approved
0.6732	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.673	Remote Similarity	NPD2354	Approved
0.6711	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6709	Remote Similarity	NPD2654	Approved
0.6707	Remote Similarity	NPD4965	Approved
0.6707	Remote Similarity	NPD4967	Phase 2
0.6707	Remote Similarity	NPD4966	Approved
0.6691	Remote Similarity	NPD164	Approved
0.6691	Remote Similarity	NPD3022	Approved
0.6691	Remote Similarity	NPD3021	Approved
0.669	Remote Similarity	NPD690	Clinical (unspecified phase)
0.669	Remote Similarity	NPD5691	Approved
0.6688	Remote Similarity	NPD275	Approved
0.6688	Remote Similarity	NPD274	Approved
0.6687	Remote Similarity	NPD1653	Approved
0.6667	Remote Similarity	NPD5049	Phase 3
0.6667	Remote Similarity	NPD520	Approved
0.6667	Remote Similarity	NPD7033	Discontinued
0.6667	Remote Similarity	NPD5536	Phase 2
0.6667	Remote Similarity	NPD422	Phase 1
0.6667	Remote Similarity	NPD4308	Phase 3
0.6667	Remote Similarity	NPD5242	Approved
0.6648	Remote Similarity	NPD6534	Approved
0.6648	Remote Similarity	NPD6535	Approved
0.6647	Remote Similarity	NPD7228	Approved
0.6645	Remote Similarity	NPD9537	Phase 1

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