NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	468.29
Volume:	509.967
LogP:	6.299
LogD:	4.493
LogS:	-4.437
# Rotatable Bonds:	10
TPSA:	83.83
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.242
Synthetic Accessibility Score:	4.236
Fsp3:	0.586
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-5.647
MDCK Permeability:	2.3578084437758662e-05
Pgp-inhibitor:	0.002
Pgp-substrate:	0.009
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.007
30% Bioavailability (F30%):	0.017

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.112
Plasma Protein Binding (PPB):	98.7040786743164%
Volume Distribution (VD):	0.194
Pgp-substrate:	1.2108312845230103%

ADMET: Metabolism

CYP1A2-inhibitor:	0.157
CYP1A2-substrate:	0.149
CYP2C19-inhibitor:	0.243
CYP2C19-substrate:	0.422
CYP2C9-inhibitor:	0.423
CYP2C9-substrate:	0.96
CYP2D6-inhibitor:	0.035
CYP2D6-substrate:	0.198
CYP3A4-inhibitor:	0.596
CYP3A4-substrate:	0.18

ADMET: Excretion

Clearance (CL):	10.904
Half-life (T1/2):	0.805

ADMET: Toxicity

hERG Blockers:	0.393
Human Hepatotoxicity (H-HT):	0.311
Drug-inuced Liver Injury (DILI):	0.031
AMES Toxicity:	0.011
Rat Oral Acute Toxicity:	0.106
Maximum Recommended Daily Dose:	0.907
Skin Sensitization:	0.861
Carcinogencity:	0.468
Eye Corrosion:	0.003
Eye Irritation:	0.021
Respiratory Toxicity:	0.932

Download Data

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

Natural Product: NPC137416

Natural Product ID:	NPC137416
*Common Name:**	(5beta,9alpha,10alpha,13S)-19-[(4-Hydroxy-trans-cinnamoyl)oxy]labd-8(20)-en-15-oic acid
IUPAC Name:	(3S)-5-[(1R,4aS,5S,8aS)-5-[[(E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxymethyl]-5,8a-dimethyl-2-methylidene-3,4,4a,6,7,8-hexahydro-1H-naphthalen-1-yl]-3-methylpentanoic acid
Synonyms:
Standard InCHIKey:	YCHBREPSJXLSOJ-HAFCEMPDSA-N
Standard InCHI:	InChI=1S/C29H40O5/c1-20(18-26(31)32)6-13-24-21(2)7-14-25-28(3,16-5-17-29(24,25)4)19-34-27(33)15-10-22-8-11-23(30)12-9-22/h8-12,15,20,24-25,30H,2,5-7,13-14,16-19H2,1,3-4H3,(H,31,32)/b15-10+/t20-,24+,25+,28+,29-/m0/s1
SMILES:	C[C@@H](CC[C@@H]1C(=C)CC[C@H]2[C@]1(CCC[C@]2(C)COC(=O)/C=C/C3=CC=C(C=C3)O)C)CC(=O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	11554552
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
NPO21782	Nuxia sphaerocephala	Species	Stilbaceae	Eukaryota	leaves	n.a.	n.a.	PMID[19299148]
NPO21782	Nuxia sphaerocephala	Species	Stilbaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO21782	Nuxia sphaerocephala	Species	Stilbaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21782	Nuxia sphaerocephala	Species	Stilbaceae	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
IC50	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	4.3	ug/ml	PMID[19299148]

☑ 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 NPC137416 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	239
0.1-0.2	1129
0.2-0.3	2077
0.3-0.4	4556
0.4-0.5	10078
0.5-0.6	9381
0.6-0.7	12197
0.7-0.8	2880
0.8-0.85	115
0.85-0.9	38
0.9-0.95	6
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9262	High Similarity	NPC265413
0.9262	High Similarity	NPC10154
0.9219	High Similarity	NPC173569
0.9219	High Similarity	NPC477874
0.9147	High Similarity	NPC249817
0.9106	High Similarity	NPC474532
0.9077	High Similarity	NPC216940
0.9077	High Similarity	NPC475482
0.9077	High Similarity	NPC471152
0.9077	High Similarity	NPC198621
0.9077	High Similarity	NPC22676
0.9008	High Similarity	NPC248287
0.9008	High Similarity	NPC234548
0.8992	High Similarity	NPC194970
0.8872	High Similarity	NPC27518
0.8872	High Similarity	NPC172311
0.8872	High Similarity	NPC304110
0.8872	High Similarity	NPC472801
0.877	High Similarity	NPC42657
0.8769	High Similarity	NPC475627
0.8769	High Similarity	NPC475457
0.8769	High Similarity	NPC475346
0.8769	High Similarity	NPC18982
0.875	High Similarity	NPC86257
0.8741	High Similarity	NPC477873
0.8741	High Similarity	NPC469447
0.8676	High Similarity	NPC25491
0.8672	High Similarity	NPC229894
0.8613	High Similarity	NPC53520
0.8605	High Similarity	NPC131684
0.8583	High Similarity	NPC275576
0.8571	High Similarity	NPC139946
0.8561	High Similarity	NPC11266
0.8551	High Similarity	NPC66894
0.8551	High Similarity	NPC8102
0.8525	High Similarity	NPC128249
0.8516	High Similarity	NPC169913
0.8516	High Similarity	NPC204579
0.8507	High Similarity	NPC477592
0.8496	Intermediate Similarity	NPC472804
0.8492	Intermediate Similarity	NPC121168
0.8487	Intermediate Similarity	NPC183700
0.848	Intermediate Similarity	NPC164852
0.8475	Intermediate Similarity	NPC31274
0.8473	Intermediate Similarity	NPC18798
0.8462	Intermediate Similarity	NPC117899
0.8462	Intermediate Similarity	NPC30174
0.8462	Intermediate Similarity	NPC288290
0.8455	Intermediate Similarity	NPC122117
0.8444	Intermediate Similarity	NPC477593
0.8429	Intermediate Similarity	NPC477483
0.8429	Intermediate Similarity	NPC325032
0.8421	Intermediate Similarity	NPC477594
0.8417	Intermediate Similarity	NPC208293
0.8413	Intermediate Similarity	NPC249340
0.8413	Intermediate Similarity	NPC162935
0.8394	Intermediate Similarity	NPC477595
0.8385	Intermediate Similarity	NPC193203
0.8372	Intermediate Similarity	NPC471935
0.8372	Intermediate Similarity	NPC110211
0.8372	Intermediate Similarity	NPC471929
0.8372	Intermediate Similarity	NPC471930
0.8369	Intermediate Similarity	NPC473719
0.8369	Intermediate Similarity	NPC279442
0.8358	Intermediate Similarity	NPC279463
0.8358	Intermediate Similarity	NPC43353
0.8358	Intermediate Similarity	NPC477596
0.8347	Intermediate Similarity	NPC17693
0.8346	Intermediate Similarity	NPC478058
0.8333	Intermediate Similarity	NPC241001
0.8333	Intermediate Similarity	NPC258073
0.8321	Intermediate Similarity	NPC155552
0.831	Intermediate Similarity	NPC327962
0.8309	Intermediate Similarity	NPC182249
0.8309	Intermediate Similarity	NPC116742
0.8309	Intermediate Similarity	NPC132723
0.8309	Intermediate Similarity	NPC139243
0.8309	Intermediate Similarity	NPC76032
0.8306	Intermediate Similarity	NPC45794
0.8306	Intermediate Similarity	NPC76308
0.8306	Intermediate Similarity	NPC325295
0.8295	Intermediate Similarity	NPC470765
0.8293	Intermediate Similarity	NPC23402
0.8281	Intermediate Similarity	NPC14141
0.8271	Intermediate Similarity	NPC165612
0.8268	Intermediate Similarity	NPC253627
0.8254	Intermediate Similarity	NPC478121
0.8254	Intermediate Similarity	NPC190501
0.8254	Intermediate Similarity	NPC318552
0.8252	Intermediate Similarity	NPC118033
0.8248	Intermediate Similarity	NPC473591
0.8248	Intermediate Similarity	NPC470617
0.8248	Intermediate Similarity	NPC470616
0.8248	Intermediate Similarity	NPC155192
0.8248	Intermediate Similarity	NPC271494
0.8244	Intermediate Similarity	NPC217431
0.8235	Intermediate Similarity	NPC260952
0.8231	Intermediate Similarity	NPC71610
0.8231	Intermediate Similarity	NPC470753
0.8231	Intermediate Similarity	NPC473220
0.8226	Intermediate Similarity	NPC28951
0.8226	Intermediate Similarity	NPC325646
0.8209	Intermediate Similarity	NPC472591
0.8209	Intermediate Similarity	NPC49742
0.8203	Intermediate Similarity	NPC11250
0.8194	Intermediate Similarity	NPC473773
0.8194	Intermediate Similarity	NPC475579
0.8188	Intermediate Similarity	NPC473612
0.8182	Intermediate Similarity	NPC194979
0.8182	Intermediate Similarity	NPC222905
0.8182	Intermediate Similarity	NPC267469
0.8182	Intermediate Similarity	NPC35160
0.8182	Intermediate Similarity	NPC87630
0.8182	Intermediate Similarity	NPC162569
0.8182	Intermediate Similarity	NPC179128
0.8182	Intermediate Similarity	NPC116292
0.8182	Intermediate Similarity	NPC214246
0.8175	Intermediate Similarity	NPC473974
0.8175	Intermediate Similarity	NPC79933
0.8175	Intermediate Similarity	NPC258366
0.8175	Intermediate Similarity	NPC31296
0.8175	Intermediate Similarity	NPC307883
0.8167	Intermediate Similarity	NPC206341
0.8156	Intermediate Similarity	NPC75295
0.8154	Intermediate Similarity	NPC49938
0.8148	Intermediate Similarity	NPC27394
0.8143	Intermediate Similarity	NPC474599
0.8143	Intermediate Similarity	NPC271451
0.814	Intermediate Similarity	NPC471187
0.814	Intermediate Similarity	NPC174991
0.814	Intermediate Similarity	NPC198014
0.8138	Intermediate Similarity	NPC105942
0.8138	Intermediate Similarity	NPC205392
0.8129	Intermediate Similarity	NPC35212
0.8125	Intermediate Similarity	NPC473579
0.8125	Intermediate Similarity	NPC475454
0.8125	Intermediate Similarity	NPC154696
0.8125	Intermediate Similarity	NPC473680
0.8125	Intermediate Similarity	NPC475311
0.8116	Intermediate Similarity	NPC79372
0.8112	Intermediate Similarity	NPC17600
0.8106	Intermediate Similarity	NPC469930
0.8106	Intermediate Similarity	NPC2596
0.8099	Intermediate Similarity	NPC472937
0.8099	Intermediate Similarity	NPC472938
0.8099	Intermediate Similarity	NPC75272
0.8099	Intermediate Similarity	NPC472936
0.8099	Intermediate Similarity	NPC88141
0.8099	Intermediate Similarity	NPC471954
0.8095	Intermediate Similarity	NPC471033
0.8095	Intermediate Similarity	NPC311091
0.8095	Intermediate Similarity	NPC203124
0.8085	Intermediate Similarity	NPC169942
0.808	Intermediate Similarity	NPC19290
0.8077	Intermediate Similarity	NPC288945
0.8077	Intermediate Similarity	NPC181334
0.8077	Intermediate Similarity	NPC184219
0.8077	Intermediate Similarity	NPC89630
0.8074	Intermediate Similarity	NPC476282
0.8071	Intermediate Similarity	NPC235557
0.8071	Intermediate Similarity	NPC310621
0.8071	Intermediate Similarity	NPC252133
0.8065	Intermediate Similarity	NPC285350
0.8065	Intermediate Similarity	NPC221275
0.806	Intermediate Similarity	NPC108553
0.806	Intermediate Similarity	NPC471851
0.8058	Intermediate Similarity	NPC29599
0.8058	Intermediate Similarity	NPC470035
0.8056	Intermediate Similarity	NPC52931
0.8051	Intermediate Similarity	NPC304638
0.8047	Intermediate Similarity	NPC259703
0.8047	Intermediate Similarity	NPC32322
0.8047	Intermediate Similarity	NPC470848
0.8047	Intermediate Similarity	NPC470849
0.8043	Intermediate Similarity	NPC202260
0.8043	Intermediate Similarity	NPC265335
0.8033	Intermediate Similarity	NPC63345
0.8031	Intermediate Similarity	NPC264976
0.8031	Intermediate Similarity	NPC263386
0.8031	Intermediate Similarity	NPC141791
0.803	Intermediate Similarity	NPC51448
0.803	Intermediate Similarity	NPC115797
0.803	Intermediate Similarity	NPC84672
0.803	Intermediate Similarity	NPC262936
0.803	Intermediate Similarity	NPC78364
0.803	Intermediate Similarity	NPC176130
0.803	Intermediate Similarity	NPC30491
0.803	Intermediate Similarity	NPC69424
0.8029	Intermediate Similarity	NPC90431
0.8029	Intermediate Similarity	NPC476699
0.8028	Intermediate Similarity	NPC258856
0.8028	Intermediate Similarity	NPC320734
0.8027	Intermediate Similarity	NPC472807
0.8017	Intermediate Similarity	NPC470039
0.8016	Intermediate Similarity	NPC471926
0.8015	Intermediate Similarity	NPC202225
0.8015	Intermediate Similarity	NPC137750
0.8015	Intermediate Similarity	NPC477893
0.8015	Intermediate Similarity	NPC477896
0.8015	Intermediate Similarity	NPC87985

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 NPC137416 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	219
0.1-0.2	774
0.2-0.3	1192
0.3-0.4	2197
0.4-0.5	2368
0.5-0.6	1567
0.6-0.7	726
0.7-0.8	104
0.8-0.85	2
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8806	High Similarity	NPD8166	Discontinued
0.8615	High Similarity	NPD6663	Approved
0.8594	High Similarity	NPD5736	Approved
0.8258	Intermediate Similarity	NPD3764	Approved
0.8254	Intermediate Similarity	NPD3019	Approved
0.8129	Intermediate Similarity	NPD7003	Approved
0.811	Intermediate Similarity	NPD2932	Approved
0.7972	Intermediate Similarity	NPD6273	Approved
0.7953	Intermediate Similarity	NPD9545	Approved
0.7931	Intermediate Similarity	NPD7458	Discontinued
0.7926	Intermediate Similarity	NPD8032	Phase 2
0.791	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7879	Intermediate Similarity	NPD2797	Approved
0.7872	Intermediate Similarity	NPD4628	Phase 3
0.781	Intermediate Similarity	NPD6355	Discontinued
0.7803	Intermediate Similarity	NPD1283	Approved
0.7801	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD7095	Approved
0.7778	Intermediate Similarity	NPD5951	Approved
0.777	Intermediate Similarity	NPD2799	Discontinued
0.7769	Intermediate Similarity	NPD3026	Approved
0.7769	Intermediate Similarity	NPD3023	Approved
0.7752	Intermediate Similarity	NPD3025	Approved
0.7752	Intermediate Similarity	NPD3024	Approved
0.7746	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7737	Intermediate Similarity	NPD4140	Approved
0.7724	Intermediate Similarity	NPD6831	Clinical (unspecified phase)
0.7721	Intermediate Similarity	NPD3268	Approved
0.7721	Intermediate Similarity	NPD6798	Discontinued
0.7714	Intermediate Similarity	NPD2935	Discontinued
0.7686	Intermediate Similarity	NPD5909	Discontinued
0.7674	Intermediate Similarity	NPD3091	Approved
0.7647	Intermediate Similarity	NPD7008	Discontinued
0.7647	Intermediate Similarity	NPD3020	Approved
0.7638	Intermediate Similarity	NPD2629	Approved
0.7609	Intermediate Similarity	NPD2979	Phase 3
0.7609	Intermediate Similarity	NPD4060	Phase 1
0.7578	Intermediate Similarity	NPD4198	Discontinued
0.7576	Intermediate Similarity	NPD1281	Approved
0.7561	Intermediate Similarity	NPD3134	Approved
0.7557	Intermediate Similarity	NPD4626	Approved
0.7538	Intermediate Similarity	NPD1894	Discontinued
0.7536	Intermediate Similarity	NPD6233	Phase 2
0.7532	Intermediate Similarity	NPD8127	Discontinued
0.7519	Intermediate Similarity	NPD9493	Approved
0.7519	Intermediate Similarity	NPD3972	Approved
0.75	Intermediate Similarity	NPD3750	Approved
0.75	Intermediate Similarity	NPD7768	Phase 2
0.75	Intermediate Similarity	NPD4110	Phase 3
0.75	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD3847	Discontinued
0.7481	Intermediate Similarity	NPD5691	Approved
0.7481	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7481	Intermediate Similarity	NPD1164	Approved
0.7481	Intermediate Similarity	NPD5585	Approved
0.748	Intermediate Similarity	NPD5535	Approved
0.7465	Intermediate Similarity	NPD5404	Approved
0.7465	Intermediate Similarity	NPD4476	Approved
0.7465	Intermediate Similarity	NPD4477	Approved
0.7465	Intermediate Similarity	NPD5406	Approved
0.7465	Intermediate Similarity	NPD5408	Approved
0.7465	Intermediate Similarity	NPD5405	Approved
0.7464	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7458	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.745	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7448	Intermediate Similarity	NPD6190	Approved
0.7447	Intermediate Similarity	NPD7097	Phase 1
0.7444	Intermediate Similarity	NPD3092	Approved
0.7444	Intermediate Similarity	NPD1535	Discovery
0.7426	Intermediate Similarity	NPD2798	Approved
0.7424	Intermediate Similarity	NPD7163	Clinical (unspecified phase)
0.7424	Intermediate Similarity	NPD3095	Discontinued
0.7422	Intermediate Similarity	NPD1241	Discontinued
0.7407	Intermediate Similarity	NPD1876	Approved
0.7397	Intermediate Similarity	NPD7236	Approved
0.7397	Intermediate Similarity	NPD7440	Discontinued
0.7395	Intermediate Similarity	NPD2859	Approved
0.7395	Intermediate Similarity	NPD2860	Approved
0.7388	Intermediate Similarity	NPD1608	Approved
0.7388	Intermediate Similarity	NPD1481	Phase 2
0.7368	Intermediate Similarity	NPD7819	Suspended
0.7361	Intermediate Similarity	NPD4534	Discontinued
0.736	Intermediate Similarity	NPD1358	Approved
0.736	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7353	Intermediate Similarity	NPD3267	Approved
0.7353	Intermediate Similarity	NPD3266	Approved
0.7353	Intermediate Similarity	NPD3094	Phase 2
0.7353	Intermediate Similarity	NPD1470	Approved
0.7348	Intermediate Similarity	NPD1651	Approved
0.7347	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7344	Intermediate Similarity	NPD6858	Approved
0.7344	Intermediate Similarity	NPD7094	Approved
0.7343	Intermediate Similarity	NPD2531	Phase 2
0.7343	Intermediate Similarity	NPD2438	Suspended
0.7338	Intermediate Similarity	NPD2313	Discontinued
0.7333	Intermediate Similarity	NPD5327	Phase 3
0.7329	Intermediate Similarity	NPD7910	Clinical (unspecified phase)
0.7323	Intermediate Similarity	NPD2181	Clinical (unspecified phase)
0.7319	Intermediate Similarity	NPD6832	Phase 2
0.7319	Intermediate Similarity	NPD2614	Approved
0.7317	Intermediate Similarity	NPD6647	Phase 2
0.7313	Intermediate Similarity	NPD1201	Approved
0.7311	Intermediate Similarity	NPD2934	Approved
0.7311	Intermediate Similarity	NPD2933	Approved
0.7308	Intermediate Similarity	NPD7157	Approved
0.7302	Intermediate Similarity	NPD2182	Approved
0.7297	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7293	Intermediate Similarity	NPD4059	Approved
0.7293	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.7292	Intermediate Similarity	NPD2346	Discontinued
0.7292	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7292	Intermediate Similarity	NPD7266	Discontinued
0.7286	Intermediate Similarity	NPD4062	Phase 3
0.7273	Intermediate Similarity	NPD4308	Phase 3
0.7244	Intermediate Similarity	NPD3021	Approved
0.7244	Intermediate Similarity	NPD3022	Approved
0.7241	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD7596	Clinical (unspecified phase)
0.7239	Intermediate Similarity	NPD3496	Discontinued
0.7237	Intermediate Similarity	NPD6677	Suspended
0.7237	Intermediate Similarity	NPD7411	Suspended
0.7226	Intermediate Similarity	NPD7075	Discontinued
0.7226	Intermediate Similarity	NPD1203	Approved
0.7222	Intermediate Similarity	NPD6099	Approved
0.7222	Intermediate Similarity	NPD6100	Approved
0.7214	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7213	Intermediate Similarity	NPD2066	Phase 3
0.7208	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7206	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7206	Intermediate Similarity	NPD4359	Approved
0.7206	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD7427	Discontinued
0.7194	Intermediate Similarity	NPD4908	Phase 1
0.7183	Intermediate Similarity	NPD230	Phase 1
0.7183	Intermediate Similarity	NPD5735	Approved
0.7177	Intermediate Similarity	NPD1930	Approved
0.7177	Intermediate Similarity	NPD1929	Approved
0.7177	Intermediate Similarity	NPD1931	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD255	Approved
0.7176	Intermediate Similarity	NPD256	Approved
0.7174	Intermediate Similarity	NPD4624	Approved
0.7174	Intermediate Similarity	NPD6007	Clinical (unspecified phase)
0.7171	Intermediate Similarity	NPD7028	Phase 2
0.7164	Intermediate Similarity	NPD1778	Approved
0.7164	Intermediate Similarity	NPD17	Approved
0.7153	Intermediate Similarity	NPD3748	Approved
0.7153	Intermediate Similarity	NPD1510	Phase 2
0.7153	Intermediate Similarity	NPD3299	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD7239	Suspended
0.7143	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7741	Discontinued
0.7133	Intermediate Similarity	NPD6353	Approved
0.7132	Intermediate Similarity	NPD6124	Clinical (unspecified phase)
0.7132	Intermediate Similarity	NPD9717	Approved
0.7123	Intermediate Similarity	NPD5958	Discontinued
0.7113	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7113	Intermediate Similarity	NPD825	Approved
0.7113	Intermediate Similarity	NPD826	Approved
0.7113	Intermediate Similarity	NPD3620	Phase 2
0.7107	Intermediate Similarity	NPD1809	Phase 2
0.7105	Intermediate Similarity	NPD3226	Approved
0.7105	Intermediate Similarity	NPD3455	Phase 2
0.7099	Intermediate Similarity	NPD690	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD5122	Clinical (unspecified phase)
0.7078	Intermediate Similarity	NPD37	Approved
0.7073	Intermediate Similarity	NPD1238	Approved
0.707	Intermediate Similarity	NPD6234	Discontinued
0.7067	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD6599	Discontinued
0.7059	Intermediate Similarity	NPD6287	Discontinued
0.7055	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD6002	Phase 3
0.7055	Intermediate Similarity	NPD6005	Phase 3
0.7055	Intermediate Similarity	NPD6004	Phase 3
0.7055	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD2344	Approved
0.7055	Intermediate Similarity	NPD6800	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD7702	Clinical (unspecified phase)
0.7051	Intermediate Similarity	NPD4967	Phase 2
0.7051	Intermediate Similarity	NPD4966	Approved
0.7051	Intermediate Similarity	NPD4965	Approved
0.705	Intermediate Similarity	NPD5647	Approved
0.7042	Intermediate Similarity	NPD7961	Discontinued
0.7034	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7034	Intermediate Similarity	NPD7033	Discontinued
0.7031	Intermediate Similarity	NPD9266	Approved
0.7031	Intermediate Similarity	NPD74	Approved
0.7029	Intermediate Similarity	NPD3225	Approved
0.7023	Intermediate Similarity	NPD7159	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD7473	Discontinued
0.7014	Intermediate Similarity	NPD6653	Approved
0.7014	Intermediate Similarity	NPD4579	Clinical (unspecified phase)
0.7013	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7013	Intermediate Similarity	NPD6873	Phase 2
0.7007	Intermediate Similarity	NPD1549	Phase 2
0.7	Intermediate Similarity	NPD4208	Discontinued
0.6993	Remote Similarity	NPD4307	Phase 2
0.6993	Remote Similarity	NPD1240	Approved
0.6992	Remote Similarity	NPD405	Clinical (unspecified phase)

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data