NPASS Compound

Structure

NPC295312 OpenBabel07101719242D 25 27 0 0 1 0 0 0 0 0999 V2000 1.8162 -1.8634 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6547 2.2660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6753 0.3511 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3220 1.0598 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3764 1.6920 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4410 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9207 1.8688 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3764 -0.6920 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4899 -0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5388 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9207 -0.8688 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9856 1.5229 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8663 -0.2367 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 -0.3090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.3220 -0.0598 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.4899 1.8090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.9856 -0.5229 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.8663 -0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7989 2.7601 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.6753 -1.3968 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8090 1.5878 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 3.3220 -0.9859 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 11 1 0 0 0 0 2 12 2 0 0 0 0 3 13 2 0 0 0 0 4 6 1 0 0 0 0 4 12 1 0 0 0 0 5 7 1 0 0 0 0 5 14 1 0 0 0 0 7 17 1 0 0 0 0 8 11 1 0 0 0 0 9 11 2 0 0 0 0 10 14 2 0 0 0 0 10 15 1 0 0 0 0 12 17 1 0 0 0 0 13 16 1 0 0 0 0 13 19 1 0 0 0 0 14 20 1 0 0 0 0 15 8 1 1 0 0 0 15 24 1 0 0 0 0 16 6 1 6 0 0 0 16 18 1 0 0 0 0 17 21 1 1 0 0 0 18 9 1 1 0 0 0 18 25 1 0 0 0 0 19 22 2 0 0 0 0 19 25 1 0 0 0 0 20 23 2 0 0 0 0 20 24 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	344.16
Volume:	356.939
LogP:	2.431
LogD:	1.864
LogS:	-3.791
# Rotatable Bonds:	0
TPSA:	79.9
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.429
Synthetic Accessibility Score:	5.805
Fsp3:	0.45
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	2
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.153
MDCK Permeability:	1.4421483683690894e-05
Pgp-inhibitor:	0.003
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.515
20% Bioavailability (F20%):	0.95
30% Bioavailability (F30%):	0.009

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.002
Plasma Protein Binding (PPB):	85.0717544555664%
Volume Distribution (VD):	0.44
Pgp-substrate:	4.331369876861572%

ADMET: Metabolism

CYP1A2-inhibitor:	0.148
CYP1A2-substrate:	0.119
CYP2C19-inhibitor:	0.086
CYP2C19-substrate:	0.064
CYP2C9-inhibitor:	0.47
CYP2C9-substrate:	0.909
CYP2D6-inhibitor:	0.023
CYP2D6-substrate:	0.705
CYP3A4-inhibitor:	0.051
CYP3A4-substrate:	0.215

ADMET: Excretion

Clearance (CL):	3.813
Half-life (T1/2):	0.562

ADMET: Toxicity

hERG Blockers:	0.006
Human Hepatotoxicity (H-HT):	0.818
Drug-inuced Liver Injury (DILI):	0.673
AMES Toxicity:	0.109
Rat Oral Acute Toxicity:	0.946
Maximum Recommended Daily Dose:	0.97
Skin Sensitization:	0.411
Carcinogencity:	0.089
Eye Corrosion:	0.003
Eye Irritation:	0.014
Respiratory Toxicity:	0.92

Download Data

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

Natural Product: NPC295312

Natural Product ID:	NPC295312
*Common Name:**	VOJUAGSYDJPMCX-JUXQZVFASA-N
IUPAC Name:	n.a.
Synonyms:	4-Methylene-5beta-hydroxyovatodiolide
Standard InCHIKey:	VOJUAGSYDJPMCX-JUXQZVFASA-N
Standard InCHI:	InChI=1S/C20H24O5/c1-11-8-15-10-14(20(23)24-15)5-7-17(21)12(2)4-6-16-13(3)19(22)25-18(16)9-11/h9-10,15-18,21H,2-8H2,1H3/b11-9+/t15-,16-,17-,18+/m1/s1
SMILES:	C/C/1=C[C@H]2[C@H](CCC(=C)[C@@H](CCC3=C[C@@H](C1)OC3=O)O)C(=C)C(=O)O2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL460462
PubChem CID:	24970921
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
NPO9613	Anisomeles indica	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18547115]
NPO9613	Anisomeles indica	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9613	Anisomeles indica	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9613	Anisomeles indica	Species	Lamiaceae	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	2

Activity Type	# Activity
CELL-LINE	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20967	CELL-LINE	Platelet	n.a.	IC50	=	41900.0	nM	PMID[572747]
NPT20967	CELL-LINE	Platelet	n.a.	IC50	=	100000.0	nM	PMID[572747]

☑ 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 NPC295312 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	190
0.1-0.2	1125
0.2-0.3	4502
0.3-0.4	8566
0.4-0.5	14870
0.5-0.6	7274
0.6-0.7	4452
0.7-0.8	1347
0.8-0.85	297
0.85-0.9	64
0.9-0.95	9
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9405	High Similarity	NPC284902
0.9294	High Similarity	NPC160138
0.908	High Similarity	NPC474032
0.907	High Similarity	NPC475703
0.8989	High Similarity	NPC179746
0.8989	High Similarity	NPC81419
0.8989	High Similarity	NPC475912
0.8977	High Similarity	NPC474761
0.8977	High Similarity	NPC106510
0.8977	High Similarity	NPC476004
0.8977	High Similarity	NPC71533
0.8966	High Similarity	NPC202672
0.8889	High Similarity	NPC81386
0.8889	High Similarity	NPC474035
0.8876	High Similarity	NPC30515
0.8876	High Similarity	NPC12172
0.8876	High Similarity	NPC208886
0.8837	High Similarity	NPC215364
0.8837	High Similarity	NPC21469
0.8824	High Similarity	NPC250315
0.8791	High Similarity	NPC304886
0.8791	High Similarity	NPC36954
0.8791	High Similarity	NPC14961
0.8791	High Similarity	NPC270013
0.8778	High Similarity	NPC475838
0.8778	High Similarity	NPC228451
0.8778	High Similarity	NPC125674
0.8764	High Similarity	NPC475855
0.8764	High Similarity	NPC51004
0.8736	High Similarity	NPC305475
0.8736	High Similarity	NPC475461
0.8721	High Similarity	NPC472957
0.8721	High Similarity	NPC472958
0.871	High Similarity	NPC473326
0.8696	High Similarity	NPC476315
0.8681	High Similarity	NPC474338
0.8681	High Similarity	NPC474247
0.8675	High Similarity	NPC93763
0.8675	High Similarity	NPC108816
0.8667	High Similarity	NPC184463
0.8667	High Similarity	NPC473321
0.8652	High Similarity	NPC307411
0.8652	High Similarity	NPC268298
0.8621	High Similarity	NPC255307
0.8621	High Similarity	NPC137033
0.8617	High Similarity	NPC288876
0.8587	High Similarity	NPC471142
0.8571	High Similarity	NPC295204
0.8571	High Similarity	NPC212486
0.8571	High Similarity	NPC273579
0.8571	High Similarity	NPC135776
0.8571	High Similarity	NPC162205
0.8571	High Similarity	NPC288240
0.8571	High Similarity	NPC476300
0.8556	High Similarity	NPC179394
0.8556	High Similarity	NPC473619
0.8556	High Similarity	NPC144133
0.8556	High Similarity	NPC129419
0.8554	High Similarity	NPC7563
0.8554	High Similarity	NPC116177
0.8554	High Similarity	NPC320630
0.8539	High Similarity	NPC153805
0.8539	High Similarity	NPC474471
0.8539	High Similarity	NPC473715
0.8539	High Similarity	NPC227379
0.8523	High Similarity	NPC122502
0.8523	High Similarity	NPC112685
0.8511	High Similarity	NPC23364
0.8511	High Similarity	NPC187268
0.8506	High Similarity	NPC114979
0.8506	High Similarity	NPC191476
0.8495	Intermediate Similarity	NPC230800
0.8495	Intermediate Similarity	NPC279621
0.8488	Intermediate Similarity	NPC173609
0.8478	Intermediate Similarity	NPC303942
0.8478	Intermediate Similarity	NPC140543
0.8478	Intermediate Similarity	NPC477131
0.8478	Intermediate Similarity	NPC57405
0.8478	Intermediate Similarity	NPC473316
0.8478	Intermediate Similarity	NPC469632
0.8478	Intermediate Similarity	NPC473330
0.8462	Intermediate Similarity	NPC300312
0.8462	Intermediate Similarity	NPC111114
0.8462	Intermediate Similarity	NPC261607
0.8462	Intermediate Similarity	NPC475925
0.8454	Intermediate Similarity	NPC100487
0.8444	Intermediate Similarity	NPC477011
0.8444	Intermediate Similarity	NPC166919
0.8438	Intermediate Similarity	NPC197835
0.8438	Intermediate Similarity	NPC303653
0.8438	Intermediate Similarity	NPC140591
0.8438	Intermediate Similarity	NPC291500
0.8438	Intermediate Similarity	NPC189609
0.8434	Intermediate Similarity	NPC123360
0.8427	Intermediate Similarity	NPC231889
0.8427	Intermediate Similarity	NPC186148
0.8409	Intermediate Similarity	NPC100921
0.8409	Intermediate Similarity	NPC165162
0.8409	Intermediate Similarity	NPC477018
0.8404	Intermediate Similarity	NPC471462
0.8391	Intermediate Similarity	NPC131669
0.8391	Intermediate Similarity	NPC473390
0.8391	Intermediate Similarity	NPC40746
0.8391	Intermediate Similarity	NPC272814
0.8391	Intermediate Similarity	NPC11620
0.8391	Intermediate Similarity	NPC169575
0.8387	Intermediate Similarity	NPC477922
0.8372	Intermediate Similarity	NPC325031
0.837	Intermediate Similarity	NPC476049
0.8367	Intermediate Similarity	NPC243998
0.8353	Intermediate Similarity	NPC470239
0.8353	Intermediate Similarity	NPC470244
0.8352	Intermediate Similarity	NPC312042
0.8352	Intermediate Similarity	NPC473448
0.8333	Intermediate Similarity	NPC150923
0.8333	Intermediate Similarity	NPC58219
0.8333	Intermediate Similarity	NPC177629
0.8316	Intermediate Similarity	NPC141191
0.8316	Intermediate Similarity	NPC474213
0.8315	Intermediate Similarity	NPC240695
0.8315	Intermediate Similarity	NPC114694
0.8315	Intermediate Similarity	NPC150755
0.8315	Intermediate Similarity	NPC142117
0.8315	Intermediate Similarity	NPC62118
0.8315	Intermediate Similarity	NPC107717
0.8315	Intermediate Similarity	NPC171174
0.8315	Intermediate Similarity	NPC477010
0.8315	Intermediate Similarity	NPC231096
0.8315	Intermediate Similarity	NPC475581
0.8315	Intermediate Similarity	NPC261721
0.8315	Intermediate Similarity	NPC164393
0.8315	Intermediate Similarity	NPC232555
0.8315	Intermediate Similarity	NPC309211
0.8298	Intermediate Similarity	NPC473859
0.8298	Intermediate Similarity	NPC477921
0.8295	Intermediate Similarity	NPC474780
0.8295	Intermediate Similarity	NPC96259
0.8295	Intermediate Similarity	NPC141193
0.8295	Intermediate Similarity	NPC476804
0.828	Intermediate Similarity	NPC198853
0.828	Intermediate Similarity	NPC323008
0.828	Intermediate Similarity	NPC262133
0.828	Intermediate Similarity	NPC470013
0.828	Intermediate Similarity	NPC476267
0.828	Intermediate Similarity	NPC470010
0.8276	Intermediate Similarity	NPC229825
0.8265	Intermediate Similarity	NPC203659
0.8261	Intermediate Similarity	NPC131209
0.8261	Intermediate Similarity	NPC133698
0.8247	Intermediate Similarity	NPC86077
0.8242	Intermediate Similarity	NPC32922
0.8242	Intermediate Similarity	NPC92974
0.8235	Intermediate Similarity	NPC471465
0.8235	Intermediate Similarity	NPC196653
0.8235	Intermediate Similarity	NPC267231
0.8222	Intermediate Similarity	NPC159750
0.8222	Intermediate Similarity	NPC473649
0.8222	Intermediate Similarity	NPC237540
0.8222	Intermediate Similarity	NPC154097
0.8222	Intermediate Similarity	NPC470401
0.8222	Intermediate Similarity	NPC248602
0.8211	Intermediate Similarity	NPC474343
0.8211	Intermediate Similarity	NPC169205
0.8211	Intermediate Similarity	NPC161493
0.8202	Intermediate Similarity	NPC1083
0.8202	Intermediate Similarity	NPC223871
0.8202	Intermediate Similarity	NPC82795
0.8202	Intermediate Similarity	NPC66346
0.8202	Intermediate Similarity	NPC473478
0.8202	Intermediate Similarity	NPC107986
0.8202	Intermediate Similarity	NPC473669
0.8202	Intermediate Similarity	NPC231009
0.8202	Intermediate Similarity	NPC103284
0.8202	Intermediate Similarity	NPC283085
0.8202	Intermediate Similarity	NPC286338
0.8202	Intermediate Similarity	NPC474547
0.8202	Intermediate Similarity	NPC132496
0.8202	Intermediate Similarity	NPC110710
0.8202	Intermediate Similarity	NPC473651
0.8202	Intermediate Similarity	NPC470755
0.8193	Intermediate Similarity	NPC476355
0.8191	Intermediate Similarity	NPC272050
0.8191	Intermediate Similarity	NPC52044
0.8191	Intermediate Similarity	NPC471141
0.8191	Intermediate Similarity	NPC213698
0.8191	Intermediate Similarity	NPC170120
0.8191	Intermediate Similarity	NPC67584
0.8191	Intermediate Similarity	NPC475659
0.8182	Intermediate Similarity	NPC223450
0.8182	Intermediate Similarity	NPC116543
0.8182	Intermediate Similarity	NPC318468
0.8172	Intermediate Similarity	NPC469692
0.8172	Intermediate Similarity	NPC11456
0.8172	Intermediate Similarity	NPC475657
0.8172	Intermediate Similarity	NPC469645
0.8163	Intermediate Similarity	NPC475945
0.8163	Intermediate Similarity	NPC110989
0.8163	Intermediate Similarity	NPC475871
0.8161	Intermediate Similarity	NPC24417
0.8152	Intermediate Similarity	NPC473904

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 NPC295312 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	173
0.1-0.2	1685
0.2-0.3	3643
0.3-0.4	2384
0.4-0.5	812
0.5-0.6	332
0.6-0.7	94
0.7-0.8	27
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7802	Intermediate Similarity	NPD1733	Clinical (unspecified phase)
0.7766	Intermediate Similarity	NPD6698	Approved
0.7766	Intermediate Similarity	NPD46	Approved
0.7579	Intermediate Similarity	NPD5785	Approved
0.7573	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7983	Approved
0.7474	Intermediate Similarity	NPD1695	Approved
0.7423	Intermediate Similarity	NPD5778	Approved
0.7423	Intermediate Similarity	NPD5779	Approved
0.7419	Intermediate Similarity	NPD5363	Approved
0.7396	Intermediate Similarity	NPD7838	Discovery
0.7391	Intermediate Similarity	NPD5362	Discontinued
0.7391	Intermediate Similarity	NPD7154	Phase 3
0.7358	Intermediate Similarity	NPD6371	Approved
0.734	Intermediate Similarity	NPD4249	Approved
0.734	Intermediate Similarity	NPD5786	Approved
0.7283	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7263	Intermediate Similarity	NPD4251	Approved
0.7263	Intermediate Similarity	NPD4250	Approved
0.7228	Intermediate Similarity	NPD4225	Approved
0.7228	Intermediate Similarity	NPD8029	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD6053	Discontinued
0.717	Intermediate Similarity	NPD6686	Approved
0.7157	Intermediate Similarity	NPD7639	Approved
0.7157	Intermediate Similarity	NPD7640	Approved
0.7097	Intermediate Similarity	NPD4269	Approved
0.7097	Intermediate Similarity	NPD4270	Approved
0.7059	Intermediate Similarity	NPD7638	Approved
0.7053	Intermediate Similarity	NPD1694	Approved
0.7053	Intermediate Similarity	NPD6082	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD7839	Suspended
0.7	Intermediate Similarity	NPD5282	Discontinued
0.6972	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6915	Remote Similarity	NPD6435	Approved
0.6882	Remote Similarity	NPD4252	Approved
0.6882	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6848	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD5331	Approved
0.6842	Remote Similarity	NPD5332	Approved
0.6809	Remote Similarity	NPD5369	Approved
0.6809	Remote Similarity	NPD4790	Discontinued
0.6771	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6768	Remote Similarity	NPD6101	Approved
0.6768	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6762	Remote Similarity	NPD5344	Discontinued
0.6702	Remote Similarity	NPD4820	Approved
0.6702	Remote Similarity	NPD4821	Approved
0.6702	Remote Similarity	NPD5368	Approved
0.6702	Remote Similarity	NPD4819	Approved
0.6702	Remote Similarity	NPD4822	Approved
0.6667	Remote Similarity	NPD6008	Approved
0.6667	Remote Similarity	NPD4268	Approved
0.6667	Remote Similarity	NPD4271	Approved
0.6667	Remote Similarity	NPD4247	Clinical (unspecified phase)
0.6634	Remote Similarity	NPD6411	Approved
0.6628	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6581	Remote Similarity	NPD8516	Approved
0.6581	Remote Similarity	NPD8515	Approved
0.6581	Remote Similarity	NPD8513	Phase 3
0.6581	Remote Similarity	NPD8517	Approved
0.6562	Remote Similarity	NPD5209	Approved
0.6559	Remote Similarity	NPD4756	Discovery
0.6542	Remote Similarity	NPD7632	Discontinued
0.6522	Remote Similarity	NPD7115	Discovery
0.6509	Remote Similarity	NPD6648	Approved
0.65	Remote Similarity	NPD7507	Approved
0.6495	Remote Similarity	NPD6110	Phase 1
0.6486	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD7637	Suspended
0.6436	Remote Similarity	NPD5370	Suspended
0.6429	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6408	Remote Similarity	NPD6399	Phase 3
0.6364	Remote Similarity	NPD7331	Phase 2
0.6344	Remote Similarity	NPD8039	Approved
0.6341	Remote Similarity	NPD7319	Approved
0.6311	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.6311	Remote Similarity	NPD8074	Phase 3
0.6306	Remote Similarity	NPD5697	Approved
0.63	Remote Similarity	NPD6422	Discontinued
0.6261	Remote Similarity	NPD4632	Approved
0.625	Remote Similarity	NPD6011	Approved
0.625	Remote Similarity	NPD6881	Approved
0.625	Remote Similarity	NPD7320	Approved
0.625	Remote Similarity	NPD7341	Phase 2
0.625	Remote Similarity	NPD6899	Approved
0.624	Remote Similarity	NPD7260	Phase 2
0.6228	Remote Similarity	NPD6649	Approved
0.6228	Remote Similarity	NPD6650	Approved
0.6216	Remote Similarity	NPD6675	Approved
0.6216	Remote Similarity	NPD7128	Approved
0.6216	Remote Similarity	NPD5739	Approved
0.6216	Remote Similarity	NPD6402	Approved
0.6198	Remote Similarity	NPD7830	Approved
0.6198	Remote Similarity	NPD7642	Approved
0.6198	Remote Similarity	NPD7829	Approved
0.6195	Remote Similarity	NPD6372	Approved
0.6195	Remote Similarity	NPD6014	Approved
0.6195	Remote Similarity	NPD6013	Approved
0.6195	Remote Similarity	NPD6012	Approved
0.6195	Remote Similarity	NPD6373	Approved
0.619	Remote Similarity	NPD7748	Approved
0.619	Remote Similarity	NPD6845	Suspended
0.6186	Remote Similarity	NPD7641	Discontinued
0.6176	Remote Similarity	NPD6903	Approved
0.6168	Remote Similarity	NPD6084	Phase 2
0.6168	Remote Similarity	NPD6083	Phase 2
0.6168	Remote Similarity	NPD7902	Approved
0.6161	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6161	Remote Similarity	NPD5701	Approved
0.6154	Remote Similarity	NPD6079	Approved
0.6154	Remote Similarity	NPD7515	Phase 2
0.6148	Remote Similarity	NPD7492	Approved
0.614	Remote Similarity	NPD6883	Approved
0.614	Remote Similarity	NPD7290	Approved
0.614	Remote Similarity	NPD7102	Approved
0.6139	Remote Similarity	NPD6684	Approved
0.6139	Remote Similarity	NPD7521	Approved
0.6139	Remote Similarity	NPD5330	Approved
0.6139	Remote Similarity	NPD6409	Approved
0.6139	Remote Similarity	NPD7334	Approved
0.6139	Remote Similarity	NPD7146	Approved
0.6139	Remote Similarity	NPD3618	Phase 1
0.6132	Remote Similarity	NPD5695	Phase 3
0.6124	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6117	Remote Similarity	NPD5328	Approved
0.6111	Remote Similarity	NPD5696	Approved
0.6102	Remote Similarity	NPD6009	Approved
0.61	Remote Similarity	NPD3133	Approved
0.61	Remote Similarity	NPD3666	Approved
0.61	Remote Similarity	NPD3665	Phase 1
0.6098	Remote Similarity	NPD6616	Approved
0.6091	Remote Similarity	NPD5211	Phase 2
0.6087	Remote Similarity	NPD6617	Approved
0.6087	Remote Similarity	NPD8130	Phase 1
0.6087	Remote Similarity	NPD6847	Approved
0.6087	Remote Similarity	NPD6869	Approved
0.6083	Remote Similarity	NPD6319	Approved
0.6083	Remote Similarity	NPD6054	Approved
0.6075	Remote Similarity	NPD5221	Approved
0.6075	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6075	Remote Similarity	NPD5222	Approved
0.6075	Remote Similarity	NPD4697	Phase 3
0.6061	Remote Similarity	NPD3667	Approved
0.6061	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.6048	Remote Similarity	NPD7078	Approved
0.6036	Remote Similarity	NPD6647	Phase 2
0.6034	Remote Similarity	NPD6882	Approved
0.6034	Remote Similarity	NPD8297	Approved
0.6033	Remote Similarity	NPD6016	Approved
0.6033	Remote Similarity	NPD5983	Phase 2
0.6033	Remote Similarity	NPD6015	Approved
0.6033	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.602	Remote Similarity	NPD4695	Discontinued
0.6019	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6019	Remote Similarity	NPD6672	Approved
0.6019	Remote Similarity	NPD5737	Approved
0.6019	Remote Similarity	NPD5173	Approved
0.6018	Remote Similarity	NPD6412	Phase 2
0.6	Remote Similarity	NPD6420	Discontinued
0.6	Remote Similarity	NPD7736	Approved
0.6	Remote Similarity	NPD6695	Phase 3
0.6	Remote Similarity	NPD5693	Phase 1
0.5984	Remote Similarity	NPD5988	Approved
0.5984	Remote Similarity	NPD6370	Approved
0.5982	Remote Similarity	NPD5141	Approved
0.5981	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.598	Remote Similarity	NPD5279	Phase 3
0.5977	Remote Similarity	NPD4246	Clinical (unspecified phase)
0.5968	Remote Similarity	NPD8451	Approved
0.5966	Remote Similarity	NPD7500	Approved
0.5965	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.5955	Remote Similarity	NPD3197	Phase 1
0.595	Remote Similarity	NPD6059	Approved
0.5948	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.5948	Remote Similarity	NPD7116	Clinical (unspecified phase)
0.5948	Remote Similarity	NPD2204	Approved
0.5941	Remote Similarity	NPD4786	Approved
0.5941	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.5935	Remote Similarity	NPD7604	Phase 2
0.5929	Remote Similarity	NPD5048	Discontinued
0.5922	Remote Similarity	NPD3573	Approved
0.592	Remote Similarity	NPD8448	Approved
0.592	Remote Similarity	NPD8293	Discontinued
0.5917	Remote Similarity	NPD7328	Approved
0.5917	Remote Similarity	NPD7327	Approved
0.5909	Remote Similarity	NPD5285	Approved
0.5909	Remote Similarity	NPD4696	Approved
0.5909	Remote Similarity	NPD5286	Approved
0.5906	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.5905	Remote Similarity	NPD5207	Approved
0.5902	Remote Similarity	NPD8033	Approved
0.5902	Remote Similarity	NPD8444	Approved
0.5888	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.5888	Remote Similarity	NPD7900	Approved
0.5887	Remote Similarity	NPD8342	Approved
0.5887	Remote Similarity	NPD8341	Approved
0.5887	Remote Similarity	NPD8340	Approved
0.5887	Remote Similarity	NPD8299	Approved
0.5882	Remote Similarity	NPD1696	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