NPASS Compound

Structure

NPC470742 OpenBabel07101718312D 30 33 0 0 1 0 0 0 0 0999 V2000 1.9487 0.2976 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9487 -6.7024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4487 -4.5685 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4487 -2.8364 0.0000 C 0 0 0 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 2.8147 -2.2024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2167 -2.7024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2167 -3.7024 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 -2.9727 -1.6287 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 1.9487 -0.7024 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.9487 -5.7024 0.0000 C 0 0 0 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 -2.7024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0827 -2.2024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5000 -0.8660 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.0827 -4.2024 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.9487 -3.7024 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 1.9487 -3.7024 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.0827 -1.2024 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.8147 -5.2024 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4487 -4.5685 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 3.4487 -2.8364 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 1.0827 -5.2024 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 13 1 0 0 0 0 2 14 1 0 0 0 0 4 27 1 0 0 0 0 5 6 1 0 0 0 0 5 13 1 0 0 0 0 6 16 1 0 0 0 0 7 8 1 0 0 0 0 7 17 1 0 0 0 0 8 19 1 0 0 0 0 9 10 2 0 0 0 0 9 15 1 0 0 0 0 10 28 1 0 0 0 0 11 18 1 0 0 0 0 12 15 2 0 0 0 0 12 28 1 0 0 0 0 13 23 1 6 0 0 0 14 24 2 0 0 0 0 14 29 1 0 0 0 0 16 17 2 0 0 0 0 16 22 1 0 0 0 0 17 23 1 0 0 0 0 18 15 1 1 0 0 0 18 30 1 0 0 0 0 19 22 1 6 0 0 0 19 29 1 0 0 0 0 20 22 1 0 0 0 0 20 25 2 0 0 0 0 20 27 1 0 0 0 0 21 23 1 0 0 0 0 21 26 2 0 0 0 0 21 30 1 0 0 0 0 22 3 1 1 0 0 0 23 11 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	416.18
Volume:	417.851
LogP:	3.003
LogD:	2.757
LogS:	-4.297
# Rotatable Bonds:	5
TPSA:	92.04
# H-Bond Aceptor:	7
# H-Bond Donor:	0
# Rings:	4
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.419
Synthetic Accessibility Score:	5.156
Fsp3:	0.609
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:	-5.085
MDCK Permeability:	6.450957880588248e-05
Pgp-inhibitor:	0.893
Pgp-substrate:	0.005
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.034
30% Bioavailability (F30%):	0.871

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.083
Plasma Protein Binding (PPB):	90.5973129272461%
Volume Distribution (VD):	2.313
Pgp-substrate:	5.788218021392822%

ADMET: Metabolism

CYP1A2-inhibitor:	0.051
CYP1A2-substrate:	0.541
CYP2C19-inhibitor:	0.921
CYP2C19-substrate:	0.722
CYP2C9-inhibitor:	0.907
CYP2C9-substrate:	0.147
CYP2D6-inhibitor:	0.012
CYP2D6-substrate:	0.097
CYP3A4-inhibitor:	0.86
CYP3A4-substrate:	0.681

ADMET: Excretion

Clearance (CL):	8.777
Half-life (T1/2):	0.082

ADMET: Toxicity

hERG Blockers:	0.007
Human Hepatotoxicity (H-HT):	0.793
Drug-inuced Liver Injury (DILI):	0.725
AMES Toxicity:	0.228
Rat Oral Acute Toxicity:	0.972
Maximum Recommended Daily Dose:	0.863
Skin Sensitization:	0.093
Carcinogencity:	0.853
Eye Corrosion:	0.047
Eye Irritation:	0.211
Respiratory Toxicity:	0.912

Download Data

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

Natural Product: NPC470742

Natural Product ID:	NPC470742
*Common Name:**	Crassifolin F
IUPAC Name:	methyl (1S,2R,5R,5'S,6R)-2-acetyloxy-5'-(furan-3-yl)-1,6-dimethyl-2'-oxospiro[2,3,4,6,7,8-hexahydronaphthalene-5,3'-oxolane]-1-carboxylate
Synonyms:	Crassifolin F
Standard InCHIKey:	UXGNFHQNRCSBPH-QJAXDWLUSA-N
Standard InCHI:	InChI=1S/C23H28O7/c1-13-5-6-16-17(7-8-19(29-14(2)24)22(16,3)20(25)27-4)23(13)11-18(30-21(23)26)15-9-10-28-12-15/h9-10,12-13,18-19H,5-8,11H2,1-4H3/t13-,18+,19-,22+,23-/m1/s1
SMILES:	COC(=O)[C@]1(C)[C@@H](CCC2=C1CC[C@H]([C@@]12C[C@H](OC1=O)c1cocc1)C)OC(=O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2208214
PubChem CID:	71461525
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones [CHEMONTID:0001538] Diterpene lactones

*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	2

Activity Type	# Activity
Cell Line	1
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	>	50000.0	nM	PMID[510244]
NPT3574	Organism	Herpes simplex virus (type 1 / strain F)	Herpes simplex virus (type 1 / strain F)	IC50	=	50.0	ug.mL-1	PMID[510243]

☑ 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 NPC470742 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	302
0.1-0.2	1326
0.2-0.3	3277
0.3-0.4	7370
0.4-0.5	12324
0.5-0.6	10461
0.6-0.7	6758
0.7-0.8	734
0.8-0.85	94
0.85-0.9	29
0.9-0.95	13
0.95-1	9

Similarity Score	Similarity Level	Natural Product ID
0.9845	High Similarity	NPC92941
0.9535	High Similarity	NPC298190
0.9474	High Similarity	NPC236532
0.9328	High Similarity	NPC220094
0.927	High Similarity	NPC470741
0.927	High Similarity	NPC223415
0.9254	High Similarity	NPC310830
0.9225	High Similarity	NPC319140
0.9225	High Similarity	NPC95567
0.9179	High Similarity	NPC146872
0.9124	High Similarity	NPC20500
0.9071	High Similarity	NPC346
0.9044	High Similarity	NPC476943
0.9015	High Similarity	NPC21460
0.9007	High Similarity	NPC221809
0.8993	High Similarity	NPC267632
0.8955	High Similarity	NPC470740
0.8929	High Similarity	NPC476944
0.8881	High Similarity	NPC195325
0.8873	High Similarity	NPC250228
0.8841	High Similarity	NPC90953
0.8811	High Similarity	NPC476941
0.8811	High Similarity	NPC476942
0.8803	High Similarity	NPC262198
0.8794	High Similarity	NPC142113
0.8788	High Similarity	NPC83178
0.8767	High Similarity	NPC57998
0.8759	High Similarity	NPC18135
0.8741	High Similarity	NPC476937
0.8741	High Similarity	NPC476938
0.8707	High Similarity	NPC44675
0.8707	High Similarity	NPC214541
0.8705	High Similarity	NPC474722
0.8699	High Similarity	NPC476939
0.8699	High Similarity	NPC476940
0.8696	High Similarity	NPC186626
0.869	High Similarity	NPC476936
0.869	High Similarity	NPC469335
0.869	High Similarity	NPC159927
0.8667	High Similarity	NPC61788
0.8662	High Similarity	NPC251865
0.8643	High Similarity	NPC56197
0.8636	High Similarity	NPC179354
0.8626	High Similarity	NPC16922
0.8621	High Similarity	NPC472654
0.8611	High Similarity	NPC470941
0.8611	High Similarity	NPC10088
0.8592	High Similarity	NPC476946
0.8591	High Similarity	NPC261597
0.8582	High Similarity	NPC207294
0.8582	High Similarity	NPC112706
0.8571	High Similarity	NPC75906
0.8571	High Similarity	NPC469503
0.8562	High Similarity	NPC196864
0.8562	High Similarity	NPC476122
0.8562	High Similarity	NPC156189
0.8562	High Similarity	NPC477404
0.8542	High Similarity	NPC471292
0.854	High Similarity	NPC471006
0.8531	High Similarity	NPC238843
0.8531	High Similarity	NPC84479
0.8531	High Similarity	NPC199044
0.8521	High Similarity	NPC473152
0.8519	High Similarity	NPC198904
0.8514	High Similarity	NPC178932
0.8514	High Similarity	NPC30222
0.8493	Intermediate Similarity	NPC470791
0.8493	Intermediate Similarity	NPC470790
0.8473	Intermediate Similarity	NPC1848
0.8467	Intermediate Similarity	NPC187149
0.8467	Intermediate Similarity	NPC299038
0.8467	Intermediate Similarity	NPC36655
0.8467	Intermediate Similarity	NPC472776
0.8467	Intermediate Similarity	NPC472778
0.8467	Intermediate Similarity	NPC472777
0.8456	Intermediate Similarity	NPC469336
0.8456	Intermediate Similarity	NPC35000
0.8456	Intermediate Similarity	NPC469850
0.8451	Intermediate Similarity	NPC205765
0.8446	Intermediate Similarity	NPC44577
0.8446	Intermediate Similarity	NPC476201
0.8444	Intermediate Similarity	NPC477039
0.8435	Intermediate Similarity	NPC46551
0.8435	Intermediate Similarity	NPC470997
0.8433	Intermediate Similarity	NPC46536
0.8433	Intermediate Similarity	NPC74612
0.8433	Intermediate Similarity	NPC138139
0.8429	Intermediate Similarity	NPC42400
0.8421	Intermediate Similarity	NPC188377
0.8421	Intermediate Similarity	NPC65735
0.8414	Intermediate Similarity	NPC62799
0.8414	Intermediate Similarity	NPC276676
0.8411	Intermediate Similarity	NPC475967
0.8411	Intermediate Similarity	NPC474932
0.8406	Intermediate Similarity	NPC218838
0.8403	Intermediate Similarity	NPC86935
0.84	Intermediate Similarity	NPC209364
0.8392	Intermediate Similarity	NPC121158
0.8389	Intermediate Similarity	NPC282445
0.8378	Intermediate Similarity	NPC116717
0.8378	Intermediate Similarity	NPC240214
0.8367	Intermediate Similarity	NPC329180
0.8367	Intermediate Similarity	NPC471001
0.8355	Intermediate Similarity	NPC191828
0.8345	Intermediate Similarity	NPC56731
0.8344	Intermediate Similarity	NPC286722
0.8344	Intermediate Similarity	NPC472283
0.8333	Intermediate Similarity	NPC471817
0.8333	Intermediate Similarity	NPC264943
0.8333	Intermediate Similarity	NPC205071
0.8333	Intermediate Similarity	NPC476262
0.8322	Intermediate Similarity	NPC33938
0.8322	Intermediate Similarity	NPC268905
0.8311	Intermediate Similarity	NPC5180
0.8309	Intermediate Similarity	NPC477966
0.8309	Intermediate Similarity	NPC477123
0.8299	Intermediate Similarity	NPC7388
0.8299	Intermediate Similarity	NPC19747
0.8298	Intermediate Similarity	NPC307401
0.8296	Intermediate Similarity	NPC23086
0.8289	Intermediate Similarity	NPC473473
0.8289	Intermediate Similarity	NPC475226
0.8289	Intermediate Similarity	NPC307383
0.8289	Intermediate Similarity	NPC475295
0.8286	Intermediate Similarity	NPC158525
0.8278	Intermediate Similarity	NPC204663
0.8278	Intermediate Similarity	NPC107646
0.8278	Intermediate Similarity	NPC126723
0.8278	Intermediate Similarity	NPC60973
0.8271	Intermediate Similarity	NPC317217
0.8264	Intermediate Similarity	NPC52412
0.8261	Intermediate Similarity	NPC89133
0.8255	Intermediate Similarity	NPC291150
0.8248	Intermediate Similarity	NPC208389
0.8248	Intermediate Similarity	NPC59502
0.8247	Intermediate Similarity	NPC663
0.8247	Intermediate Similarity	NPC419
0.8247	Intermediate Similarity	NPC165218
0.8247	Intermediate Similarity	NPC469846
0.8247	Intermediate Similarity	NPC224394
0.8244	Intermediate Similarity	NPC243704
0.8243	Intermediate Similarity	NPC234494
0.8243	Intermediate Similarity	NPC211625
0.8239	Intermediate Similarity	NPC472376
0.8235	Intermediate Similarity	NPC305016
0.8231	Intermediate Similarity	NPC471174
0.8231	Intermediate Similarity	NPC224418
0.8231	Intermediate Similarity	NPC255414
0.8224	Intermediate Similarity	NPC195131
0.8224	Intermediate Similarity	NPC470118
0.8224	Intermediate Similarity	NPC472772
0.8224	Intermediate Similarity	NPC167142
0.8224	Intermediate Similarity	NPC249021
0.8219	Intermediate Similarity	NPC41182
0.8214	Intermediate Similarity	NPC471998
0.8212	Intermediate Similarity	NPC281258
0.8207	Intermediate Similarity	NPC80635
0.8205	Intermediate Similarity	NPC100333
0.82	Intermediate Similarity	NPC471002
0.82	Intermediate Similarity	NPC182427
0.82	Intermediate Similarity	NPC29695
0.82	Intermediate Similarity	NPC308205
0.82	Intermediate Similarity	NPC322546
0.8194	Intermediate Similarity	NPC276735
0.8182	Intermediate Similarity	NPC69028
0.8182	Intermediate Similarity	NPC211777
0.8182	Intermediate Similarity	NPC197596
0.8182	Intermediate Similarity	NPC5079
0.8182	Intermediate Similarity	NPC202260
0.8182	Intermediate Similarity	NPC149896
0.8176	Intermediate Similarity	NPC93666
0.8175	Intermediate Similarity	NPC477040
0.8175	Intermediate Similarity	NPC476917
0.8175	Intermediate Similarity	NPC327527
0.817	Intermediate Similarity	NPC477403
0.817	Intermediate Similarity	NPC474611
0.8169	Intermediate Similarity	NPC310043
0.8163	Intermediate Similarity	NPC233763
0.8163	Intermediate Similarity	NPC470999
0.8158	Intermediate Similarity	NPC469485
0.8158	Intermediate Similarity	NPC104736
0.8158	Intermediate Similarity	NPC263265
0.8156	Intermediate Similarity	NPC476947
0.8154	Intermediate Similarity	NPC150895
0.8151	Intermediate Similarity	NPC137295
0.8148	Intermediate Similarity	NPC477038
0.8148	Intermediate Similarity	NPC477965
0.8146	Intermediate Similarity	NPC34421
0.8146	Intermediate Similarity	NPC237259
0.8146	Intermediate Similarity	NPC98206
0.8143	Intermediate Similarity	NPC474425
0.8143	Intermediate Similarity	NPC474407
0.8143	Intermediate Similarity	NPC474426
0.8141	Intermediate Similarity	NPC472141
0.8141	Intermediate Similarity	NPC478178
0.8134	Intermediate Similarity	NPC477967
0.8134	Intermediate Similarity	NPC36255
0.8133	Intermediate Similarity	NPC272590
0.8129	Intermediate Similarity	NPC136340
0.8129	Intermediate Similarity	NPC234660

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 NPC470742 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	266
0.1-0.2	973
0.2-0.3	2038
0.3-0.4	2712
0.4-0.5	2044
0.5-0.6	888
0.6-0.7	221
0.7-0.8	7
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
0.8092	Intermediate Similarity	NPD5760	Phase 2
0.8092	Intermediate Similarity	NPD5761	Phase 2
0.7885	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.745	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7355	Intermediate Similarity	NPD920	Approved
0.7353	Intermediate Similarity	NPD8434	Phase 2
0.729	Intermediate Similarity	NPD6273	Approved
0.7241	Intermediate Similarity	NPD6832	Phase 2
0.7226	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD1471	Phase 3
0.72	Intermediate Similarity	NPD2799	Discontinued
0.716	Intermediate Similarity	NPD6764	Approved
0.716	Intermediate Similarity	NPD6765	Approved
0.7114	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD2346	Discontinued
0.7097	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7078	Intermediate Similarity	NPD4628	Phase 3
0.7039	Intermediate Similarity	NPD2935	Discontinued
0.6994	Remote Similarity	NPD6785	Approved
0.6994	Remote Similarity	NPD6784	Approved
0.6986	Remote Similarity	NPD1019	Discontinued
0.698	Remote Similarity	NPD8032	Phase 2
0.6937	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD2979	Phase 3
0.6913	Remote Similarity	NPD2313	Discontinued
0.6909	Remote Similarity	NPD919	Approved
0.6903	Remote Similarity	NPD1243	Approved
0.6901	Remote Similarity	NPD5585	Approved
0.6899	Remote Similarity	NPD2532	Approved
0.6899	Remote Similarity	NPD2534	Approved
0.6899	Remote Similarity	NPD2533	Approved
0.6894	Remote Similarity	NPD6599	Discontinued
0.6871	Remote Similarity	NPD7819	Suspended
0.6867	Remote Similarity	NPD5494	Approved
0.6863	Remote Similarity	NPD3748	Approved
0.6861	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.686	Remote Similarity	NPD6559	Discontinued
0.6859	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD1241	Discontinued
0.6828	Remote Similarity	NPD9717	Approved
0.6828	Remote Similarity	NPD3972	Approved
0.6821	Remote Similarity	NPD4307	Phase 2
0.6818	Remote Similarity	NPD1551	Phase 2
0.6818	Remote Similarity	NPD2438	Suspended
0.6818	Remote Similarity	NPD2796	Approved
0.6786	Remote Similarity	NPD6808	Phase 2
0.6776	Remote Similarity	NPD447	Suspended
0.6774	Remote Similarity	NPD2344	Approved
0.6759	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6759	Remote Similarity	NPD1281	Approved
0.6752	Remote Similarity	NPD4110	Phase 3
0.6752	Remote Similarity	NPD7003	Approved
0.6752	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6736	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6735	Remote Similarity	NPD1876	Approved
0.6728	Remote Similarity	NPD3226	Approved
0.6727	Remote Similarity	NPD5616	Clinical (unspecified phase)
0.6726	Remote Similarity	NPD1247	Approved
0.6725	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6711	Remote Similarity	NPD4140	Approved
0.6689	Remote Similarity	NPD3266	Approved
0.6689	Remote Similarity	NPD3267	Approved
0.6689	Remote Similarity	NPD2797	Approved
0.6689	Remote Similarity	NPD411	Approved
0.6689	Remote Similarity	NPD1203	Approved
0.6688	Remote Similarity	NPD2800	Approved
0.6687	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6355	Discontinued
0.6667	Remote Similarity	NPD1933	Approved
0.6667	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5691	Approved
0.6667	Remote Similarity	NPD6002	Phase 3
0.6667	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6004	Phase 3
0.6667	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6005	Phase 3
0.6667	Remote Similarity	NPD4359	Approved
0.6647	Remote Similarity	NPD3749	Approved
0.6646	Remote Similarity	NPD3750	Approved
0.6645	Remote Similarity	NPD4308	Phase 3
0.6644	Remote Similarity	NPD2798	Approved
0.6627	Remote Similarity	NPD8127	Discontinued
0.6625	Remote Similarity	NPD6799	Approved
0.6624	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6622	Remote Similarity	NPD1283	Approved
0.6621	Remote Similarity	NPD17	Approved
0.6604	Remote Similarity	NPD2309	Approved
0.6603	Remote Similarity	NPD2531	Phase 2
0.6594	Remote Similarity	NPD2182	Approved
0.6587	Remote Similarity	NPD4967	Phase 2
0.6587	Remote Similarity	NPD4966	Approved
0.6587	Remote Similarity	NPD7768	Phase 2
0.6587	Remote Similarity	NPD4965	Approved
0.6582	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6579	Remote Similarity	NPD3268	Approved
0.6579	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6577	Remote Similarity	NPD1049	Clinical (unspecified phase)
0.6562	Remote Similarity	NPD7236	Approved
0.6554	Remote Similarity	NPD5327	Phase 3
0.6548	Remote Similarity	NPD7075	Discontinued
0.6545	Remote Similarity	NPD7411	Suspended
0.6536	Remote Similarity	NPD4870	Approved
0.6533	Remote Similarity	NPD5647	Approved
0.6527	Remote Similarity	NPD5402	Approved
0.6524	Remote Similarity	NPD7458	Discontinued
0.6513	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6509	Remote Similarity	NPD6234	Discontinued
0.6506	Remote Similarity	NPD6801	Discontinued
0.6506	Remote Similarity	NPD6280	Approved
0.6506	Remote Similarity	NPD6279	Approved
0.65	Remote Similarity	NPD3887	Approved
0.6494	Remote Similarity	NPD5844	Phase 1
0.6486	Remote Similarity	NPD1608	Approved
0.6485	Remote Similarity	NPD7028	Phase 2
0.6481	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD3764	Approved
0.6467	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6463	Remote Similarity	NPD3496	Discontinued
0.6453	Remote Similarity	NPD3926	Phase 2
0.6452	Remote Similarity	NPD4622	Approved
0.6452	Remote Similarity	NPD4618	Approved
0.6449	Remote Similarity	NPD3134	Approved
0.6438	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6438	Remote Similarity	NPD8166	Discontinued
0.6438	Remote Similarity	NPD1651	Approved
0.6429	Remote Similarity	NPD3817	Phase 2
0.6429	Remote Similarity	NPD6233	Phase 2
0.6429	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD6663	Approved
0.6424	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6415	Remote Similarity	NPD1549	Phase 2
0.641	Remote Similarity	NPD6653	Approved
0.6407	Remote Similarity	NPD37	Approved
0.6404	Remote Similarity	NPD8312	Approved
0.6404	Remote Similarity	NPD8313	Approved
0.6402	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6402	Remote Similarity	NPD5403	Approved
0.6395	Remote Similarity	NPD5710	Approved
0.6395	Remote Similarity	NPD5711	Approved
0.6395	Remote Similarity	NPD1778	Approved
0.6395	Remote Similarity	NPD4626	Approved
0.6395	Remote Similarity	NPD6232	Discontinued
0.6392	Remote Similarity	NPD4476	Approved
0.6392	Remote Similarity	NPD4477	Approved
0.6391	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6391	Remote Similarity	NPD3882	Suspended
0.638	Remote Similarity	NPD5401	Approved
0.6379	Remote Similarity	NPD7473	Discontinued
0.6378	Remote Similarity	NPD8404	Phase 2
0.6369	Remote Similarity	NPD5689	Approved
0.6369	Remote Similarity	NPD5688	Approved
0.6364	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD4107	Approved
0.6364	Remote Similarity	NPD7239	Suspended
0.6364	Remote Similarity	NPD6798	Discontinued
0.6358	Remote Similarity	NPD6362	Approved
0.6352	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6352	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6351	Remote Similarity	NPD7457	Clinical (unspecified phase)
0.6347	Remote Similarity	NPD5889	Approved
0.6347	Remote Similarity	NPD6873	Phase 2
0.6347	Remote Similarity	NPD5890	Approved
0.6345	Remote Similarity	NPD9493	Approved
0.6343	Remote Similarity	NPD3818	Discontinued
0.6337	Remote Similarity	NPD6959	Discontinued
0.633	Remote Similarity	NPD4482	Phase 3
0.6329	Remote Similarity	NPD7033	Discontinued
0.6322	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6312	Remote Similarity	NPD2424	Discontinued
0.6312	Remote Similarity	NPD4534	Discontinued
0.631	Remote Similarity	NPD1934	Approved
0.6309	Remote Similarity	NPD1611	Approved
0.6304	Remote Similarity	NPD164	Approved
0.6301	Remote Similarity	NPD7229	Phase 3
0.6301	Remote Similarity	NPD7315	Approved
0.6299	Remote Similarity	NPD7095	Approved
0.6294	Remote Similarity	NPD5535	Approved
0.6287	Remote Similarity	NPD4380	Phase 2
0.6286	Remote Similarity	NPD1358	Approved
0.6282	Remote Similarity	NPD4060	Phase 1
0.6282	Remote Similarity	NPD3142	Approved
0.6282	Remote Similarity	NPD3140	Approved
0.6275	Remote Similarity	NPD5736	Approved
0.6266	Remote Similarity	NPD7097	Phase 1
0.6259	Remote Similarity	NPD1894	Discontinued
0.6258	Remote Similarity	NPD7440	Discontinued
0.6257	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.625	Remote Similarity	NPD7228	Approved
0.625	Remote Similarity	NPD2353	Approved
0.625	Remote Similarity	NPD5762	Approved
0.625	Remote Similarity	NPD2355	Clinical (unspecified phase)
0.625	Remote Similarity	NPD5763	Approved
0.6243	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6242	Remote Similarity	NPD5735	Approved
0.6242	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.6235	Remote Similarity	NPD5353	Approved
0.6234	Remote Similarity	NPD2614	Approved
0.623	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6226	Remote Similarity	NPD1510	Phase 2
0.6224	Remote Similarity	NPD1609	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