NPASS Compound

Structure

NPC470741 OpenBabel07101718302D 27 31 0 0 1 0 0 0 0 0999 V2000 -0.2167 2.7024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3535 -1.2230 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9770 -0.3413 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2115 -0.0671 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9945 1.8366 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6687 0.0861 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9727 1.6287 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9487 2.7024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1691 1.6092 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1637 0.2274 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3536 1.7024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0827 2.2024 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.4945 0.9706 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9487 0.7024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8147 2.2024 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.5000 0.8660 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.8147 1.2024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5946 0.3340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9781 0.2079 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7658 0.8934 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.0827 1.2024 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.4936 0.7721 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7213 -0.4612 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.5246 -0.6636 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.0772 0.6341 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.7658 2.5115 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 12 1 0 0 0 0 2 24 1 0 0 0 0 3 4 1 0 0 0 0 3 6 1 0 0 0 0 4 14 1 0 0 0 0 5 7 2 0 0 0 0 5 13 1 0 0 0 0 6 20 1 0 0 0 0 7 25 1 0 0 0 0 8 12 1 0 0 0 0 9 16 1 0 0 0 0 10 13 2 0 0 0 0 10 25 1 0 0 0 0 11 20 1 0 0 0 0 11 26 1 0 0 0 0 12 21 1 6 0 0 0 14 17 2 0 0 0 0 14 21 1 0 0 0 0 15 8 1 6 0 0 0 15 17 1 0 0 0 0 15 26 1 0 0 0 0 16 13 1 6 0 0 0 16 27 1 0 0 0 0 17 20 1 0 0 0 0 18 22 2 0 0 0 0 18 24 1 0 0 0 0 19 21 1 0 0 0 0 19 23 2 0 0 0 0 19 27 1 0 0 0 0 20 18 1 1 0 0 0 21 9 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	372.16
Volume:	368.549
LogP:	2.862
LogD:	2.34
LogS:	-4.276
# Rotatable Bonds:	3
TPSA:	74.97
# H-Bond Aceptor:	6
# H-Bond Donor:	0
# Rings:	5
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.586
Synthetic Accessibility Score:	5.326
Fsp3:	0.619
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:	-5.287
MDCK Permeability:	2.659359415702056e-05
Pgp-inhibitor:	0.187
Pgp-substrate:	0.246
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.086
30% Bioavailability (F30%):	0.151

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.413
Plasma Protein Binding (PPB):	95.02294158935547%
Volume Distribution (VD):	2.694
Pgp-substrate:	2.172959327697754%

ADMET: Metabolism

CYP1A2-inhibitor:	0.071
CYP1A2-substrate:	0.798
CYP2C19-inhibitor:	0.925
CYP2C19-substrate:	0.801
CYP2C9-inhibitor:	0.848
CYP2C9-substrate:	0.053
CYP2D6-inhibitor:	0.031
CYP2D6-substrate:	0.128
CYP3A4-inhibitor:	0.912
CYP3A4-substrate:	0.714

ADMET: Excretion

Clearance (CL):	8.036
Half-life (T1/2):	0.09

ADMET: Toxicity

hERG Blockers:	0.06
Human Hepatotoxicity (H-HT):	0.764
Drug-inuced Liver Injury (DILI):	0.292
AMES Toxicity:	0.76
Rat Oral Acute Toxicity:	0.958
Maximum Recommended Daily Dose:	0.922
Skin Sensitization:	0.092
Carcinogencity:	0.883
Eye Corrosion:	0.004
Eye Irritation:	0.091
Respiratory Toxicity:	0.934

Download Data

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

Natural Product: NPC470741

Natural Product ID:	NPC470741
*Common Name:**	Crassifolin D
IUPAC Name:	n.a.
Synonyms:	Crassifolin D
Standard InCHIKey:	HXZOVFHWQXUMMV-WNSPWUEXSA-N
Standard InCHI:	InChI=1S/C21H24O6/c1-12-8-15-17-14(4-3-6-20(17,11-26-15)18(22)24-2)21(12)9-16(27-19(21)23)13-5-7-25-10-13/h5,7,10,12,15-16H,3-4,6,8-9,11H2,1-2H3/t12-,15+,16+,20-,21-/m0/s1
SMILES:	CC1CC2C3=C(C14CC(OC4=O)C5=COC=C5)CCCC3(CO2)C(=O)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2208213
PubChem CID:	71456086
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000050] Lactones [CHEMONTID:0001245] Gamma butyrolactones

*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
NPO32991	croton crassifolius	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23194476]
NPO32991	croton crassifolius	Species	Euphorbiaceae	Eukaryota	Roots	n.a.	n.a.	PMID[28150949]
NPO32991	croton crassifolius	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32003565]

☑ 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
NPT3574	Organism	Herpes simplex virus (type 1 / strain F)	Herpes simplex virus (type 1 / strain F)	IC50	=	50.0	ug.mL-1	PMID[468692]

☑ 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 NPC470741 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	347
0.1-0.2	1415
0.2-0.3	3369
0.3-0.4	7685
0.4-0.5	12239
0.5-0.6	9349
0.6-0.7	7344
0.7-0.8	804
0.8-0.85	102
0.85-0.9	23
0.9-0.95	15
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
0.9424	High Similarity	NPC223415
0.9407	High Similarity	NPC92941
0.9301	High Similarity	NPC195325
0.927	High Similarity	NPC470742
0.9203	High Similarity	NPC220094
0.9161	High Similarity	NPC221809
0.9161	High Similarity	NPC250228
0.9143	High Similarity	NPC20500
0.913	High Similarity	NPC310830
0.8973	High Similarity	NPC476936
0.8958	High Similarity	NPC346
0.8929	High Similarity	NPC476943
0.8919	High Similarity	NPC57998
0.8912	High Similarity	NPC18135
0.8897	High Similarity	NPC21460
0.8897	High Similarity	NPC470941
0.8865	High Similarity	NPC90953
0.8859	High Similarity	NPC214541
0.8859	High Similarity	NPC44675
0.8857	High Similarity	NPC186626
0.8851	High Similarity	NPC75906
0.8844	High Similarity	NPC469335
0.8844	High Similarity	NPC159927
0.8832	High Similarity	NPC298190
0.8819	High Similarity	NPC251865
0.8819	High Similarity	NPC86935
0.8815	High Similarity	NPC319140
0.8815	High Similarity	NPC95567
0.8811	High Similarity	NPC473152
0.8794	High Similarity	NPC236532
0.8786	High Similarity	NPC146872
0.8776	High Similarity	NPC472654
0.875	High Similarity	NPC267632
0.875	High Similarity	NPC191828
0.8742	High Similarity	NPC261597
0.8725	High Similarity	NPC44577
0.8725	High Similarity	NPC469503
0.8716	High Similarity	NPC476122
0.8716	High Similarity	NPC196864
0.8716	High Similarity	NPC5180
0.8716	High Similarity	NPC156189
0.8716	High Similarity	NPC477404
0.8707	High Similarity	NPC476942
0.8707	High Similarity	NPC476941
0.869	High Similarity	NPC142113
0.869	High Similarity	NPC84479
0.8667	High Similarity	NPC178932
0.8667	High Similarity	NPC30222
0.8658	High Similarity	NPC291150
0.8658	High Similarity	NPC116717
0.8649	High Similarity	NPC471001
0.8649	High Similarity	NPC470790
0.8649	High Similarity	NPC329180
0.8649	High Similarity	NPC470791
0.8639	High Similarity	NPC476938
0.8639	High Similarity	NPC476937
0.8639	High Similarity	NPC10088
0.8636	High Similarity	NPC419
0.8618	High Similarity	NPC472778
0.8618	High Similarity	NPC187149
0.8618	High Similarity	NPC36655
0.8618	High Similarity	NPC299038
0.8618	High Similarity	NPC472776
0.8618	High Similarity	NPC472777
0.8609	High Similarity	NPC264943
0.8609	High Similarity	NPC469336
0.8609	High Similarity	NPC35000
0.8609	High Similarity	NPC469850
0.86	High Similarity	NPC476201
0.86	High Similarity	NPC476940
0.86	High Similarity	NPC476939
0.86	High Similarity	NPC308205
0.86	High Similarity	NPC322546
0.8571	High Similarity	NPC62799
0.8571	High Similarity	NPC470740
0.8562	High Similarity	NPC474932
0.8562	High Similarity	NPC475967
0.8562	High Similarity	NPC476944
0.8562	High Similarity	NPC475226
0.8562	High Similarity	NPC137295
0.8553	High Similarity	NPC209364
0.8553	High Similarity	NPC60973
0.8552	High Similarity	NPC121158
0.8543	High Similarity	NPC282445
0.8533	High Similarity	NPC240214
0.8526	High Similarity	NPC472141
0.8516	High Similarity	NPC165218
0.8506	High Similarity	NPC305016
0.8497	Intermediate Similarity	NPC470118
0.8497	Intermediate Similarity	NPC472283
0.8497	Intermediate Similarity	NPC286722
0.8493	Intermediate Similarity	NPC205071
0.8487	Intermediate Similarity	NPC476262
0.8477	Intermediate Similarity	NPC29695
0.8477	Intermediate Similarity	NPC471002
0.8477	Intermediate Similarity	NPC182427
0.8477	Intermediate Similarity	NPC268905
0.8456	Intermediate Similarity	NPC7388
0.8456	Intermediate Similarity	NPC19747
0.8451	Intermediate Similarity	NPC158525
0.8446	Intermediate Similarity	NPC262198
0.8446	Intermediate Similarity	NPC276676
0.8446	Intermediate Similarity	NPC470999
0.8442	Intermediate Similarity	NPC475295
0.8442	Intermediate Similarity	NPC473473
0.8442	Intermediate Similarity	NPC307383
0.8442	Intermediate Similarity	NPC477403
0.844	Intermediate Similarity	NPC471006
0.8431	Intermediate Similarity	NPC263265
0.8431	Intermediate Similarity	NPC204663
0.8431	Intermediate Similarity	NPC107646
0.8431	Intermediate Similarity	NPC126723
0.8414	Intermediate Similarity	NPC56197
0.8408	Intermediate Similarity	NPC478178
0.8408	Intermediate Similarity	NPC214600
0.8406	Intermediate Similarity	NPC83178
0.84	Intermediate Similarity	NPC211625
0.8397	Intermediate Similarity	NPC224394
0.8397	Intermediate Similarity	NPC469846
0.8397	Intermediate Similarity	NPC663
0.8394	Intermediate Similarity	NPC179354
0.8392	Intermediate Similarity	NPC46896
0.8389	Intermediate Similarity	NPC255414
0.8389	Intermediate Similarity	NPC471174
0.8387	Intermediate Similarity	NPC477402
0.8378	Intermediate Similarity	NPC41182
0.8377	Intermediate Similarity	NPC472772
0.8377	Intermediate Similarity	NPC214495
0.8377	Intermediate Similarity	NPC249021
0.8377	Intermediate Similarity	NPC197137
0.8377	Intermediate Similarity	NPC470119
0.8377	Intermediate Similarity	NPC45101
0.8377	Intermediate Similarity	NPC195131
0.8377	Intermediate Similarity	NPC167142
0.8367	Intermediate Similarity	NPC80635
0.8366	Intermediate Similarity	NPC141538
0.8366	Intermediate Similarity	NPC296807
0.8366	Intermediate Similarity	NPC155939
0.8356	Intermediate Similarity	NPC205765
0.8354	Intermediate Similarity	NPC478179
0.8354	Intermediate Similarity	NPC100333
0.8344	Intermediate Similarity	NPC46551
0.8344	Intermediate Similarity	NPC123088
0.8333	Intermediate Similarity	NPC5079
0.8333	Intermediate Similarity	NPC310043
0.8333	Intermediate Similarity	NPC149896
0.8333	Intermediate Similarity	NPC211777
0.8333	Intermediate Similarity	NPC69028
0.8333	Intermediate Similarity	NPC197596
0.8323	Intermediate Similarity	NPC237155
0.8323	Intermediate Similarity	NPC262872
0.8323	Intermediate Similarity	NPC474611
0.8322	Intermediate Similarity	NPC471292
0.8312	Intermediate Similarity	NPC469485
0.8312	Intermediate Similarity	NPC104736
0.8311	Intermediate Similarity	NPC238843
0.8311	Intermediate Similarity	NPC199044
0.8302	Intermediate Similarity	NPC327922
0.8289	Intermediate Similarity	NPC471000
0.8288	Intermediate Similarity	NPC156077
0.8288	Intermediate Similarity	NPC67003
0.828	Intermediate Similarity	NPC469338
0.828	Intermediate Similarity	NPC292389
0.828	Intermediate Similarity	NPC234660
0.828	Intermediate Similarity	NPC471168
0.828	Intermediate Similarity	NPC51568
0.828	Intermediate Similarity	NPC472139
0.828	Intermediate Similarity	NPC198047
0.8278	Intermediate Similarity	NPC69647
0.8278	Intermediate Similarity	NPC125182
0.8273	Intermediate Similarity	NPC137570
0.8269	Intermediate Similarity	NPC25255
0.8269	Intermediate Similarity	NPC472653
0.8269	Intermediate Similarity	NPC475381
0.8269	Intermediate Similarity	NPC335761
0.8267	Intermediate Similarity	NPC216755
0.8264	Intermediate Similarity	NPC214572
0.8258	Intermediate Similarity	NPC475066
0.8258	Intermediate Similarity	NPC469847
0.8258	Intermediate Similarity	NPC173544
0.8258	Intermediate Similarity	NPC304692
0.8255	Intermediate Similarity	NPC34056
0.8252	Intermediate Similarity	NPC471998
0.8248	Intermediate Similarity	NPC16922
0.8247	Intermediate Similarity	NPC92979
0.8243	Intermediate Similarity	NPC243577
0.8239	Intermediate Similarity	NPC476861
0.8239	Intermediate Similarity	NPC476850
0.8239	Intermediate Similarity	NPC472651
0.8235	Intermediate Similarity	NPC246164
0.8228	Intermediate Similarity	NPC470182
0.8228	Intermediate Similarity	NPC146991
0.8228	Intermediate Similarity	NPC470940
0.8228	Intermediate Similarity	NPC469849
0.8228	Intermediate Similarity	NPC276551
0.8224	Intermediate Similarity	NPC470997
0.8219	Intermediate Similarity	NPC474722
0.8217	Intermediate Similarity	NPC207978
0.8217	Intermediate Similarity	NPC472767
0.8217	Intermediate Similarity	NPC472668

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 NPC470741 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	287
0.1-0.2	1056
0.2-0.3	2233
0.3-0.4	2715
0.4-0.5	1970
0.5-0.6	693
0.6-0.7	192
0.7-0.8	3
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8247	Intermediate Similarity	NPD5761	Phase 2
0.8247	Intermediate Similarity	NPD5760	Phase 2
0.8038	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7628	Intermediate Similarity	NPD920	Approved
0.75	Intermediate Similarity	NPD8434	Phase 2
0.75	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7372	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7244	Intermediate Similarity	NPD4628	Phase 3
0.7209	Intermediate Similarity	NPD6765	Approved
0.7209	Intermediate Similarity	NPD6764	Approved
0.7179	Intermediate Similarity	NPD1243	Approved
0.716	Intermediate Similarity	NPD6599	Discontinued
0.7097	Intermediate Similarity	NPD2796	Approved
0.7067	Intermediate Similarity	NPD6832	Phase 2
0.7066	Intermediate Similarity	NPD919	Approved
0.7063	Intermediate Similarity	NPD2533	Approved
0.7063	Intermediate Similarity	NPD2534	Approved
0.7063	Intermediate Similarity	NPD2532	Approved
0.7051	Intermediate Similarity	NPD1471	Phase 3
0.7045	Intermediate Similarity	NPD6785	Approved
0.7045	Intermediate Similarity	NPD6784	Approved
0.703	Intermediate Similarity	NPD7819	Suspended
0.7024	Intermediate Similarity	NPD5494	Approved
0.6987	Remote Similarity	NPD1551	Phase 2
0.6977	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6962	Remote Similarity	NPD2800	Approved
0.6957	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6928	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD2799	Discontinued
0.6923	Remote Similarity	NPD3748	Approved
0.6918	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD3749	Approved
0.6894	Remote Similarity	NPD6799	Approved
0.689	Remote Similarity	NPD3226	Approved
0.6882	Remote Similarity	NPD1247	Approved
0.6855	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD2346	Discontinued
0.6835	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD6004	Phase 3
0.6835	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD6005	Phase 3
0.6835	Remote Similarity	NPD6002	Phase 3
0.6821	Remote Similarity	NPD1019	Discontinued
0.6818	Remote Similarity	NPD6559	Discontinued
0.681	Remote Similarity	NPD6273	Approved
0.6807	Remote Similarity	NPD7411	Suspended
0.6805	Remote Similarity	NPD7075	Discontinued
0.6803	Remote Similarity	NPD17	Approved
0.6792	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6766	Remote Similarity	NPD6801	Discontinued
0.6753	Remote Similarity	NPD2313	Discontinued
0.6748	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6744	Remote Similarity	NPD6808	Phase 2
0.673	Remote Similarity	NPD2344	Approved
0.6709	Remote Similarity	NPD7033	Discontinued
0.6708	Remote Similarity	NPD3750	Approved
0.6687	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6687	Remote Similarity	NPD1549	Phase 2
0.6686	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD1608	Approved
0.6667	Remote Similarity	NPD9717	Approved
0.6667	Remote Similarity	NPD3972	Approved
0.6667	Remote Similarity	NPD2935	Discontinued
0.6667	Remote Similarity	NPD4307	Phase 2
0.6648	Remote Similarity	NPD5844	Phase 1
0.6647	Remote Similarity	NPD7768	Phase 2
0.6645	Remote Similarity	NPD3267	Approved
0.6645	Remote Similarity	NPD1049	Clinical (unspecified phase)
0.6645	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6645	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6645	Remote Similarity	NPD3266	Approved
0.6627	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6625	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6625	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6609	Remote Similarity	NPD3926	Phase 2
0.6605	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.66	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6588	Remote Similarity	NPD5402	Approved
0.6588	Remote Similarity	NPD3817	Phase 2
0.6577	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6573	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6571	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6566	Remote Similarity	NPD5403	Approved
0.6564	Remote Similarity	NPD2309	Approved
0.6552	Remote Similarity	NPD5710	Approved
0.6552	Remote Similarity	NPD5711	Approved
0.6552	Remote Similarity	NPD6232	Discontinued
0.655	Remote Similarity	NPD4966	Approved
0.655	Remote Similarity	NPD4967	Phase 2
0.655	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.655	Remote Similarity	NPD4965	Approved
0.655	Remote Similarity	NPD3882	Suspended
0.6548	Remote Similarity	NPD4380	Phase 2
0.6545	Remote Similarity	NPD5401	Approved
0.6538	Remote Similarity	NPD3268	Approved
0.6536	Remote Similarity	NPD2797	Approved
0.6536	Remote Similarity	NPD1203	Approved
0.6534	Remote Similarity	NPD7473	Discontinued
0.6519	Remote Similarity	NPD1933	Approved
0.6519	Remote Similarity	NPD447	Suspended
0.6515	Remote Similarity	NPD8404	Phase 2
0.6512	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.651	Remote Similarity	NPD5585	Approved
0.6508	Remote Similarity	NPD4107	Approved
0.6503	Remote Similarity	NPD7003	Approved
0.65	Remote Similarity	NPD4308	Phase 3
0.65	Remote Similarity	NPD1510	Phase 2
0.6497	Remote Similarity	NPD8032	Phase 2
0.6497	Remote Similarity	NPD3818	Discontinued
0.6494	Remote Similarity	NPD2798	Approved
0.6494	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6494	Remote Similarity	NPD6959	Discontinued
0.6494	Remote Similarity	NPD8127	Discontinued
0.6491	Remote Similarity	NPD5616	Clinical (unspecified phase)
0.6488	Remote Similarity	NPD7458	Discontinued
0.6478	Remote Similarity	NPD1607	Approved
0.6474	Remote Similarity	NPD4482	Phase 3
0.6474	Remote Similarity	NPD6234	Discontinued
0.6471	Remote Similarity	NPD1934	Approved
0.6471	Remote Similarity	NPD6280	Approved
0.6471	Remote Similarity	NPD6279	Approved
0.6467	Remote Similarity	NPD1778	Approved
0.6467	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6464	Remote Similarity	NPD8313	Approved
0.6464	Remote Similarity	NPD8312	Approved
0.646	Remote Similarity	NPD6100	Approved
0.646	Remote Similarity	NPD6099	Approved
0.6457	Remote Similarity	NPD7229	Phase 3
0.6456	Remote Similarity	NPD1240	Approved
0.6456	Remote Similarity	NPD2979	Phase 3
0.6446	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6438	Remote Similarity	NPD1241	Discontinued
0.6433	Remote Similarity	NPD3764	Approved
0.6433	Remote Similarity	NPD411	Approved
0.6424	Remote Similarity	NPD7236	Approved
0.6415	Remote Similarity	NPD6355	Discontinued
0.6393	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6389	Remote Similarity	NPD5953	Discontinued
0.6384	Remote Similarity	NPD2403	Approved
0.6375	Remote Similarity	NPD6651	Approved
0.6374	Remote Similarity	NPD37	Approved
0.6369	Remote Similarity	NPD7286	Phase 2
0.6364	Remote Similarity	NPD3887	Approved
0.6364	Remote Similarity	NPD1876	Approved
0.6359	Remote Similarity	NPD8150	Discontinued
0.6358	Remote Similarity	NPD2438	Suspended
0.6337	Remote Similarity	NPD2801	Approved
0.6333	Remote Similarity	NPD9545	Approved
0.6319	Remote Similarity	NPD2182	Approved
0.6316	Remote Similarity	NPD5889	Approved
0.6316	Remote Similarity	NPD5890	Approved
0.6313	Remote Similarity	NPD7177	Discontinued
0.6313	Remote Similarity	NPD7799	Discontinued
0.6312	Remote Similarity	NPD4622	Approved
0.6312	Remote Similarity	NPD4618	Approved
0.631	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6307	Remote Similarity	NPD7199	Phase 2
0.6303	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6303	Remote Similarity	NPD4110	Phase 3
0.6301	Remote Similarity	NPD5353	Approved
0.6299	Remote Similarity	NPD4359	Approved
0.6291	Remote Similarity	NPD5691	Approved
0.629	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6287	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6282	Remote Similarity	NPD5647	Approved
0.6278	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6275	Remote Similarity	NPD1281	Approved
0.6266	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.625	Remote Similarity	NPD4140	Approved
0.6244	Remote Similarity	NPD5619	Clinical (unspecified phase)
0.6242	Remote Similarity	NPD2654	Approved
0.6236	Remote Similarity	NPD5242	Approved
0.6236	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6235	Remote Similarity	NPD7239	Suspended
0.6235	Remote Similarity	NPD5688	Approved
0.6235	Remote Similarity	NPD5689	Approved
0.623	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6228	Remote Similarity	NPD6652	Clinical (unspecified phase)
0.6226	Remote Similarity	NPD1296	Phase 2
0.6222	Remote Similarity	NPD7228	Approved
0.6221	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6221	Remote Similarity	NPD6385	Approved
0.6221	Remote Similarity	NPD6386	Approved
0.622	Remote Similarity	NPD5762	Approved
0.622	Remote Similarity	NPD5763	Approved
0.6213	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.6211	Remote Similarity	NPD230	Phase 1
0.6209	Remote Similarity	NPD3496	Discontinued
0.6207	Remote Similarity	NPD4288	Approved
0.6201	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6201	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6201	Remote Similarity	NPD6166	Phase 2
0.62	Remote Similarity	NPD9493	Approved
0.6198	Remote Similarity	NPD8285	Discontinued
0.619	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.619	Remote Similarity	NPD1511	Approved
0.6188	Remote Similarity	NPD4870	Approved
0.618	Remote Similarity	NPD7315	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