NPASS Compound

Structure

NPC162935 OpenBabel07101718322D 23 25 0 0 1 0 0 0 0 0999 V2000 -5.1962 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.5000 0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5981 -4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.7321 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5000 0.8660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 12 1 0 0 0 0 2 12 1 0 0 0 0 5 8 1 0 0 0 0 5 9 1 0 0 0 0 6 7 1 0 0 0 0 6 13 1 0 0 0 0 7 17 1 0 0 0 0 8 19 1 0 0 0 0 9 20 1 0 0 0 0 10 13 2 0 0 0 0 10 14 1 0 0 0 0 11 15 2 0 0 0 0 11 16 1 0 0 0 0 12 14 1 0 0 0 0 13 15 1 0 0 0 0 14 16 2 0 0 0 0 15 19 1 0 0 0 0 16 21 1 0 0 0 0 17 19 1 1 0 0 0 17 20 1 0 0 0 0 18 20 1 0 0 0 0 18 22 2 0 0 0 0 18 23 1 0 0 0 0 19 3 1 1 0 0 0 20 4 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	316.2
Volume:	344.632
LogP:	4.479
LogD:	3.844
LogS:	-3.868
# Rotatable Bonds:	2
TPSA:	57.53
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.837
Synthetic Accessibility Score:	3.628
Fsp3:	0.65
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.978
MDCK Permeability:	2.448062878102064e-05
Pgp-inhibitor:	0.033
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.008
20% Bioavailability (F20%):	0.414
30% Bioavailability (F30%):	0.972

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.082
Plasma Protein Binding (PPB):	97.05184173583984%
Volume Distribution (VD):	0.355
Pgp-substrate:	4.08083438873291%

ADMET: Metabolism

CYP1A2-inhibitor:	0.102
CYP1A2-substrate:	0.847
CYP2C19-inhibitor:	0.037
CYP2C19-substrate:	0.824
CYP2C9-inhibitor:	0.229
CYP2C9-substrate:	0.371
CYP2D6-inhibitor:	0.061
CYP2D6-substrate:	0.234
CYP3A4-inhibitor:	0.192
CYP3A4-substrate:	0.216

ADMET: Excretion

Clearance (CL):	1.737
Half-life (T1/2):	0.258

ADMET: Toxicity

hERG Blockers:	0.016
Human Hepatotoxicity (H-HT):	0.215
Drug-inuced Liver Injury (DILI):	0.046
AMES Toxicity:	0.013
Rat Oral Acute Toxicity:	0.262
Maximum Recommended Daily Dose:	0.861
Skin Sensitization:	0.588
Carcinogencity:	0.174
Eye Corrosion:	0.006
Eye Irritation:	0.572
Respiratory Toxicity:	0.802

Download Data

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

Natural Product: NPC162935

Natural Product ID:	NPC162935
*Common Name:**	Lambertic Acid
IUPAC Name:	(1S,4aS,10aR)-6-hydroxy-1,4a-dimethyl-7-propan-2-yl-2,3,4,9,10,10a-hexahydrophenanthrene-1-carboxylic acid
Synonyms:	Lambertic Acid
Standard InCHIKey:	AYDJDNNMKHXZOQ-RLLQIKCJSA-N
Standard InCHI:	InChI=1S/C20H28O3/c1-12(2)14-10-13-6-7-17-19(3,15(13)11-16(14)21)8-5-9-20(17,4)18(22)23/h10-12,17,21H,5-9H2,1-4H3,(H,22,23)/t17-,19-,20+/m1/s1
SMILES:	CC(c1cc2CC[C@@H]3[C@](c2cc1O)(C)CCC[C@]3(C)C(=O)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL519807
PubChem CID:	13370049
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids

*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
NPO14242	Maytenus laevis	Species	Celastraceae	Eukaryota	bark	Leticia, Colombia	n.a.	PMID[15568791]
NPO14242	Maytenus laevis	Species	Celastraceae	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
Others	6

Activity Type	# Activity
Cell Line	6

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT927	Cell Line	PBMC	Homo sapiens	Activity	=	59.8	pg/ml	PMID[465674]
NPT927	Cell Line	PBMC	Homo sapiens	Activity	=	1454.4	pg/ml	PMID[465674]
NPT927	Cell Line	PBMC	Homo sapiens	Activity	<	7.8	pg/ml	PMID[465674]

☑ 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 NPC162935 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	258
0.1-0.2	1401
0.2-0.3	2649
0.3-0.4	7477
0.4-0.5	10919
0.5-0.6	9337
0.6-0.7	8665
0.7-0.8	1768
0.8-0.85	129
0.85-0.9	69
0.9-0.95	17
0.95-1	8

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC249340
0.9739	High Similarity	NPC241001
0.9573	High Similarity	NPC121168
0.9565	High Similarity	NPC42657
0.9483	High Similarity	NPC478121
0.9407	High Similarity	NPC11250
0.9402	High Similarity	NPC259703
0.9402	High Similarity	NPC32322
0.9328	High Similarity	NPC471187
0.9322	High Similarity	NPC154696
0.925	High Similarity	NPC181334
0.9244	High Similarity	NPC176208
0.9174	High Similarity	NPC137750
0.916	High Similarity	NPC253627
0.9076	High Similarity	NPC164852
0.9048	High Similarity	NPC49742
0.9035	High Similarity	NPC176279
0.9035	High Similarity	NPC260323
0.9024	High Similarity	NPC69424
0.9024	High Similarity	NPC176130
0.9024	High Similarity	NPC78364
0.9024	High Similarity	NPC84672
0.9008	High Similarity	NPC198014
0.8992	High Similarity	NPC318552
0.8992	High Similarity	NPC190501
0.8983	High Similarity	NPC328694
0.8889	High Similarity	NPC243305
0.8889	High Similarity	NPC192948
0.8889	High Similarity	NPC35797
0.888	High Similarity	NPC276238
0.8871	High Similarity	NPC72667
0.8862	High Similarity	NPC87985
0.8852	High Similarity	NPC275145
0.8828	High Similarity	NPC293454
0.8814	High Similarity	NPC38893
0.8814	High Similarity	NPC477137
0.8814	High Similarity	NPC471668
0.8814	High Similarity	NPC308311
0.881	High Similarity	NPC108129
0.8803	High Similarity	NPC195922
0.8793	High Similarity	NPC250323
0.879	High Similarity	NPC254492
0.8783	High Similarity	NPC141782
0.878	High Similarity	NPC199273
0.875	High Similarity	NPC476282
0.874	High Similarity	NPC471851
0.8739	High Similarity	NPC304510
0.8739	High Similarity	NPC172219
0.873	High Similarity	NPC171460
0.873	High Similarity	NPC131684
0.873	High Similarity	NPC303910
0.8684	High Similarity	NPC151477
0.8682	High Similarity	NPC213122
0.8667	High Similarity	NPC471671
0.8655	High Similarity	NPC219112
0.8651	High Similarity	NPC3009
0.8651	High Similarity	NPC229894
0.8644	High Similarity	NPC268160
0.864	High Similarity	NPC71610
0.8632	High Similarity	NPC46940
0.8629	High Similarity	NPC15127
0.8621	High Similarity	NPC475002
0.8621	High Similarity	NPC95126
0.8621	High Similarity	NPC13482
0.8618	High Similarity	NPC478058
0.8605	High Similarity	NPC78307
0.8605	High Similarity	NPC477139
0.8595	High Similarity	NPC126002
0.8595	High Similarity	NPC79933
0.8595	High Similarity	NPC93071
0.8595	High Similarity	NPC473974
0.8595	High Similarity	NPC31296
0.8595	High Similarity	NPC469644
0.8595	High Similarity	NPC258366
0.8594	High Similarity	NPC258073
0.8594	High Similarity	NPC18798
0.8594	High Similarity	NPC291001
0.8583	High Similarity	NPC117899
0.8583	High Similarity	NPC477136
0.8583	High Similarity	NPC206028
0.8571	High Similarity	NPC147179
0.8559	High Similarity	NPC715
0.855	High Similarity	NPC472308
0.8547	High Similarity	NPC95716
0.8538	High Similarity	NPC202225
0.8538	High Similarity	NPC27394
0.8527	High Similarity	NPC165612
0.8509	High Similarity	NPC117115
0.8507	High Similarity	NPC272907
0.8507	High Similarity	NPC2681
0.8504	High Similarity	NPC96024
0.8504	High Similarity	NPC193203
0.85	High Similarity	NPC308828
0.85	High Similarity	NPC92
0.85	High Similarity	NPC469663
0.8468	Intermediate Similarity	NPC282577
0.8462	Intermediate Similarity	NPC111845
0.845	Intermediate Similarity	NPC476847
0.8448	Intermediate Similarity	NPC11554
0.8435	Intermediate Similarity	NPC21594
0.8433	Intermediate Similarity	NPC3218
0.843	Intermediate Similarity	NPC16030
0.8425	Intermediate Similarity	NPC30491
0.8425	Intermediate Similarity	NPC262936
0.8417	Intermediate Similarity	NPC469719
0.8413	Intermediate Similarity	NPC137416
0.84	Intermediate Similarity	NPC273683
0.8397	Intermediate Similarity	NPC477594
0.839	Intermediate Similarity	NPC322753
0.839	Intermediate Similarity	NPC151537
0.839	Intermediate Similarity	NPC77772
0.8376	Intermediate Similarity	NPC58865
0.8374	Intermediate Similarity	NPC183339
0.8374	Intermediate Similarity	NPC234337
0.8374	Intermediate Similarity	NPC133389
0.8362	Intermediate Similarity	NPC228737
0.8361	Intermediate Similarity	NPC469609
0.8361	Intermediate Similarity	NPC154030
0.8346	Intermediate Similarity	NPC475957
0.8333	Intermediate Similarity	NPC477596
0.8333	Intermediate Similarity	NPC279463
0.8333	Intermediate Similarity	NPC153088
0.8333	Intermediate Similarity	NPC75432
0.8321	Intermediate Similarity	NPC475346
0.8321	Intermediate Similarity	NPC475627
0.8321	Intermediate Similarity	NPC138472
0.8321	Intermediate Similarity	NPC475457
0.8321	Intermediate Similarity	NPC18982
0.8319	Intermediate Similarity	NPC286222
0.8306	Intermediate Similarity	NPC21216
0.8305	Intermediate Similarity	NPC132720
0.8268	Intermediate Similarity	NPC123506
0.825	Intermediate Similarity	NPC317869
0.8248	Intermediate Similarity	NPC477207
0.824	Intermediate Similarity	NPC369
0.824	Intermediate Similarity	NPC293831
0.8235	Intermediate Similarity	NPC266937
0.8235	Intermediate Similarity	NPC470770
0.8231	Intermediate Similarity	NPC249425
0.8226	Intermediate Similarity	NPC135467
0.8226	Intermediate Similarity	NPC260832
0.822	Intermediate Similarity	NPC314187
0.8217	Intermediate Similarity	NPC48248
0.8211	Intermediate Similarity	NPC206
0.8209	Intermediate Similarity	NPC477592
0.8203	Intermediate Similarity	NPC100414
0.8203	Intermediate Similarity	NPC321822
0.8203	Intermediate Similarity	NPC325294
0.8203	Intermediate Similarity	NPC43000
0.8197	Intermediate Similarity	NPC141001
0.8197	Intermediate Similarity	NPC212891
0.8195	Intermediate Similarity	NPC290803
0.8195	Intermediate Similarity	NPC472804
0.8195	Intermediate Similarity	NPC173569
0.8195	Intermediate Similarity	NPC477874
0.8195	Intermediate Similarity	NPC43353
0.8195	Intermediate Similarity	NPC103082
0.8189	Intermediate Similarity	NPC10154
0.8189	Intermediate Similarity	NPC173978
0.8189	Intermediate Similarity	NPC111088
0.8189	Intermediate Similarity	NPC265413
0.8188	Intermediate Similarity	NPC126707
0.8182	Intermediate Similarity	NPC471534
0.8182	Intermediate Similarity	NPC221275
0.8175	Intermediate Similarity	NPC184935
0.8168	Intermediate Similarity	NPC72669
0.8168	Intermediate Similarity	NPC474517
0.8167	Intermediate Similarity	NPC177962
0.8167	Intermediate Similarity	NPC471179
0.8167	Intermediate Similarity	NPC62867
0.8167	Intermediate Similarity	NPC228425
0.8158	Intermediate Similarity	NPC211885
0.8148	Intermediate Similarity	NPC4214
0.8148	Intermediate Similarity	NPC477593
0.8143	Intermediate Similarity	NPC5568
0.814	Intermediate Similarity	NPC108164
0.8136	Intermediate Similarity	NPC470039
0.8134	Intermediate Similarity	NPC249817
0.8134	Intermediate Similarity	NPC118919
0.813	Intermediate Similarity	NPC299180
0.813	Intermediate Similarity	NPC160199
0.812	Intermediate Similarity	NPC271274
0.812	Intermediate Similarity	NPC194970
0.8116	Intermediate Similarity	NPC100242
0.811	Intermediate Similarity	NPC174991
0.8099	Intermediate Similarity	NPC322239
0.8092	Intermediate Similarity	NPC253488
0.8092	Intermediate Similarity	NPC470725
0.8092	Intermediate Similarity	NPC475102
0.8088	Intermediate Similarity	NPC79372
0.8083	Intermediate Similarity	NPC471188
0.8074	Intermediate Similarity	NPC277559
0.8074	Intermediate Similarity	NPC475482
0.8074	Intermediate Similarity	NPC22676
0.8074	Intermediate Similarity	NPC198621
0.8074	Intermediate Similarity	NPC216940
0.8074	Intermediate Similarity	NPC62272
0.8074	Intermediate Similarity	NPC53001
0.8074	Intermediate Similarity	NPC471152
0.8074	Intermediate Similarity	NPC49911

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 NPC162935 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	271
0.1-0.2	909
0.2-0.3	1225
0.3-0.4	2537
0.4-0.5	2313
0.5-0.6	1306
0.6-0.7	484
0.7-0.8	97
0.8-0.85	6
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8992	High Similarity	NPD3019	Approved
0.8833	High Similarity	NPD2932	Approved
0.8594	High Similarity	NPD6663	Approved
0.8571	High Similarity	NPD5736	Approved
0.8306	Intermediate Similarity	NPD3026	Approved
0.8306	Intermediate Similarity	NPD3023	Approved
0.8293	Intermediate Similarity	NPD3025	Approved
0.8293	Intermediate Similarity	NPD3024	Approved
0.8189	Intermediate Similarity	NPD1283	Approved
0.8102	Intermediate Similarity	NPD7003	Approved
0.8074	Intermediate Similarity	NPD5404	Approved
0.8074	Intermediate Similarity	NPD5406	Approved
0.8074	Intermediate Similarity	NPD5408	Approved
0.8074	Intermediate Similarity	NPD5405	Approved
0.8065	Intermediate Similarity	NPD3091	Approved
0.8051	Intermediate Similarity	NPD2342	Discontinued
0.8033	Intermediate Similarity	NPD5951	Approved
0.8017	Intermediate Similarity	NPD7635	Approved
0.7953	Intermediate Similarity	NPD1281	Approved
0.7953	Intermediate Similarity	NPD1201	Approved
0.7937	Intermediate Similarity	NPD4059	Approved
0.7937	Intermediate Similarity	NPD4626	Approved
0.7895	Intermediate Similarity	NPD8032	Phase 2
0.7842	Intermediate Similarity	NPD8166	Discontinued
0.7812	Intermediate Similarity	NPD3092	Approved
0.7807	Intermediate Similarity	NPD1809	Phase 2
0.7759	Intermediate Similarity	NPD3020	Approved
0.7739	Intermediate Similarity	NPD288	Approved
0.7737	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7717	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7717	Intermediate Similarity	NPD1651	Approved
0.771	Intermediate Similarity	NPD1470	Approved
0.7656	Intermediate Similarity	NPD7163	Clinical (unspecified phase)
0.7656	Intermediate Similarity	NPD3095	Discontinued
0.7652	Intermediate Similarity	NPD844	Approved
0.7623	Intermediate Similarity	NPD4750	Phase 3
0.7609	Intermediate Similarity	NPD3299	Clinical (unspecified phase)
0.7589	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7578	Intermediate Similarity	NPD5691	Approved
0.7576	Intermediate Similarity	NPD1164	Approved
0.7576	Intermediate Similarity	NPD3094	Phase 2
0.7574	Intermediate Similarity	NPD4140	Approved
0.7574	Intermediate Similarity	NPD2979	Phase 3
0.7574	Intermediate Similarity	NPD4060	Phase 1
0.7565	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.7554	Intermediate Similarity	NPD6100	Approved
0.7554	Intermediate Similarity	NPD6099	Approved
0.7552	Intermediate Similarity	NPD7390	Discontinued
0.7542	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.7535	Intermediate Similarity	NPD7910	Clinical (unspecified phase)
0.7519	Intermediate Similarity	NPD2286	Discontinued
0.75	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD2859	Approved
0.75	Intermediate Similarity	NPD2860	Approved
0.748	Intermediate Similarity	NPD3022	Approved
0.748	Intermediate Similarity	NPD3021	Approved
0.7478	Intermediate Similarity	NPD845	Approved
0.7464	Intermediate Similarity	NPD4097	Suspended
0.7448	Intermediate Similarity	NPD6273	Approved
0.7444	Intermediate Similarity	NPD2797	Approved
0.7442	Intermediate Similarity	NPD4093	Discontinued
0.7429	Intermediate Similarity	NPD2935	Discontinued
0.7426	Intermediate Similarity	NPD3764	Approved
0.7424	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7415	Intermediate Similarity	NPD7458	Discontinued
0.7414	Intermediate Similarity	NPD2933	Approved
0.7414	Intermediate Similarity	NPD2934	Approved
0.7385	Intermediate Similarity	NPD1751	Approved
0.7376	Intermediate Similarity	NPD2346	Discontinued
0.7353	Intermediate Similarity	NPD7095	Approved
0.7344	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7323	Intermediate Similarity	NPD2629	Approved
0.7305	Intermediate Similarity	NPD2438	Suspended
0.7305	Intermediate Similarity	NPD2531	Phase 2
0.7305	Intermediate Similarity	NPD4476	Approved
0.7305	Intermediate Similarity	NPD4477	Approved
0.7297	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7279	Intermediate Similarity	NPD2606	Approved
0.7279	Intermediate Similarity	NPD2605	Approved
0.7266	Intermediate Similarity	NPD256	Approved
0.7266	Intermediate Similarity	NPD255	Approved
0.726	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7259	Intermediate Similarity	NPD4624	Approved
0.7258	Intermediate Similarity	NPD6831	Clinical (unspecified phase)
0.7252	Intermediate Similarity	NPD1778	Approved
0.7241	Intermediate Similarity	NPD1088	Approved
0.7234	Intermediate Similarity	NPD2799	Discontinued
0.7226	Intermediate Similarity	NPD7008	Discontinued
0.7226	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7226	Intermediate Similarity	NPD5155	Approved
0.7226	Intermediate Similarity	NPD5156	Approved
0.7222	Intermediate Similarity	NPD6124	Clinical (unspecified phase)
0.7218	Intermediate Similarity	NPD1608	Approved
0.7209	Intermediate Similarity	NPD7325	Clinical (unspecified phase)
0.7206	Intermediate Similarity	NPD3637	Approved
0.7206	Intermediate Similarity	NPD3635	Approved
0.7206	Intermediate Similarity	NPD3636	Approved
0.7194	Intermediate Similarity	NPD3620	Phase 2
0.7194	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7181	Intermediate Similarity	NPD3226	Approved
0.7174	Intermediate Similarity	NPD6798	Discontinued
0.7174	Intermediate Similarity	NPD3268	Approved
0.7167	Intermediate Similarity	NPD2066	Phase 3
0.7164	Intermediate Similarity	NPD1755	Approved
0.7153	Intermediate Similarity	NPD3594	Approved
0.7153	Intermediate Similarity	NPD3595	Approved
0.7152	Intermediate Similarity	NPD37	Approved
0.7143	Intermediate Similarity	NPD1611	Approved
0.7143	Intermediate Similarity	NPD6355	Discontinued
0.7132	Intermediate Similarity	NPD2195	Approved
0.7132	Intermediate Similarity	NPD2194	Approved
0.7121	Intermediate Similarity	NPD4589	Approved
0.7119	Intermediate Similarity	NPD688	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD6232	Discontinued
0.7111	Intermediate Similarity	NPD6696	Suspended
0.7109	Intermediate Similarity	NPD7159	Clinical (unspecified phase)
0.7103	Intermediate Similarity	NPD4110	Phase 3
0.7103	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD4625	Phase 3
0.7092	Intermediate Similarity	NPD4579	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD7473	Discontinued
0.7083	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7069	Intermediate Similarity	NPD1090	Approved
0.7069	Intermediate Similarity	NPD1089	Approved
0.7069	Intermediate Similarity	NPD1086	Approved
0.7063	Intermediate Similarity	NPD1792	Phase 2
0.7059	Intermediate Similarity	NPD8438	Clinical (unspecified phase)
0.7054	Intermediate Similarity	NPD497	Approved
0.7049	Intermediate Similarity	NPD940	Approved
0.7049	Intermediate Similarity	NPD846	Approved
0.7047	Intermediate Similarity	NPD7427	Discontinued
0.7045	Intermediate Similarity	NPD5585	Approved
0.704	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD5327	Phase 3
0.7034	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7032	Intermediate Similarity	NPD6234	Discontinued
0.7027	Intermediate Similarity	NPD2532	Approved
0.7027	Intermediate Similarity	NPD2533	Approved
0.7027	Intermediate Similarity	NPD2534	Approved
0.7013	Intermediate Similarity	NPD4967	Phase 2
0.7013	Intermediate Similarity	NPD4966	Approved
0.7013	Intermediate Similarity	NPD4965	Approved
0.7007	Intermediate Similarity	NPD257	Approved
0.7007	Intermediate Similarity	NPD258	Approved
0.7007	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7007	Intermediate Similarity	NPD2798	Approved
0.7007	Intermediate Similarity	NPD3300	Phase 2
0.7	Intermediate Similarity	NPD4198	Discontinued
0.6993	Remote Similarity	NPD7742	Approved
0.6993	Remote Similarity	NPD7743	Approved
0.6992	Remote Similarity	NPD17	Approved
0.6992	Remote Similarity	NPD1931	Clinical (unspecified phase)
0.6992	Remote Similarity	NPD1930	Approved
0.6992	Remote Similarity	NPD1929	Approved
0.6986	Remote Similarity	NPD4628	Phase 3
0.6986	Remote Similarity	NPD3750	Approved
0.6986	Remote Similarity	NPD3400	Discontinued
0.6984	Remote Similarity	NPD9266	Approved
0.6984	Remote Similarity	NPD74	Approved
0.6983	Remote Similarity	NPD800	Approved
0.6977	Remote Similarity	NPD498	Approved
0.6977	Remote Similarity	NPD495	Approved
0.6977	Remote Similarity	NPD496	Approved
0.6977	Remote Similarity	NPD2228	Approved
0.6977	Remote Similarity	NPD2234	Approved
0.6977	Remote Similarity	NPD2229	Approved
0.6975	Remote Similarity	NPD1693	Approved
0.697	Remote Similarity	NPD1759	Phase 1
0.697	Remote Similarity	NPD5303	Approved
0.697	Remote Similarity	NPD5304	Approved
0.6963	Remote Similarity	NPD3972	Approved
0.6957	Remote Similarity	NPD4208	Discontinued
0.695	Remote Similarity	NPD6346	Approved
0.6947	Remote Similarity	NPD9568	Approved
0.6947	Remote Similarity	NPD9493	Approved
0.6947	Remote Similarity	NPD7340	Approved
0.694	Remote Similarity	NPD3847	Discontinued
0.6935	Remote Similarity	NPD5909	Discontinued
0.6934	Remote Similarity	NPD4339	Clinical (unspecified phase)
0.6929	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6912	Remote Similarity	NPD4749	Approved
0.6906	Remote Similarity	NPD2614	Approved
0.6905	Remote Similarity	NPD9264	Approved
0.6905	Remote Similarity	NPD9267	Approved
0.6905	Remote Similarity	NPD9263	Approved
0.6901	Remote Similarity	NPD5735	Approved
0.6899	Remote Similarity	NPD5535	Approved
0.6897	Remote Similarity	NPD4725	Approved
0.6897	Remote Similarity	NPD4721	Approved
0.6897	Remote Similarity	NPD4726	Approved
0.6894	Remote Similarity	NPD7644	Approved
0.6894	Remote Similarity	NPD1758	Phase 1
0.6889	Remote Similarity	NPD5351	Clinical (unspecified phase)
0.6889	Remote Similarity	NPD5350	Clinical (unspecified phase)
0.6889	Remote Similarity	NPD1535	Discovery
0.6887	Remote Similarity	NPD2370	Clinical (unspecified phase)
0.6883	Remote Similarity	NPD7819	Suspended
0.6875	Remote Similarity	NPD4308	Phase 3
0.6866	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6866	Remote Similarity	NPD4199	Phase 3

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