NPASS Compound

Structure

NPC264546 OpenBabel07101718332D 25 27 0 0 1 0 0 0 0 0999 V2000 0.7615 -2.4945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3007 1.0055 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7026 -0.4945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2026 -1.3605 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1045 0.0055 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9706 -2.4945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8366 -1.9945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4781 -0.6581 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8366 1.0055 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3849 1.1215 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9706 0.5055 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8090 -1.4013 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3794 1.2260 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1045 -1.9945 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.4347 0.5055 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 -1.8366 -0.9945 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.7026 0.5055 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.7026 -0.4945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9706 -0.4945 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.1045 -0.9945 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.7861 2.1395 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.4347 -0.4945 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.5686 1.0055 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 14 1 0 0 0 0 2 15 1 0 0 0 0 3 19 1 0 0 0 0 4 19 1 0 0 0 0 5 20 1 0 0 0 0 6 7 1 0 0 0 0 6 14 1 0 0 0 0 7 17 1 0 0 0 0 8 12 1 0 0 0 0 8 16 1 0 0 0 0 9 11 1 0 0 0 0 9 18 1 0 0 0 0 10 13 1 0 0 0 0 10 16 2 0 0 0 0 11 20 1 0 0 0 0 13 22 2 0 0 0 0 14 21 1 6 0 0 0 15 23 2 0 0 0 0 15 24 1 0 0 0 0 16 25 1 0 0 0 0 17 19 1 0 0 0 0 17 20 1 1 0 0 0 18 19 1 0 0 0 0 18 24 1 1 0 0 0 20 21 1 6 0 0 0 21 12 1 1 0 0 0 21 25 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	348.23
Volume:	373.354
LogP:	3.81
LogD:	3.591
LogS:	-4.503
# Rotatable Bonds:	3
TPSA:	52.6
# H-Bond Aceptor:	4
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.421
Synthetic Accessibility Score:	5.045
Fsp3:	0.81
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.616
MDCK Permeability:	1.9935529053327627e-05
Pgp-inhibitor:	0.99
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.013
30% Bioavailability (F30%):	0.148

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.297
Plasma Protein Binding (PPB):	77.38167572021484%
Volume Distribution (VD):	1.296
Pgp-substrate:	21.267183303833008%

ADMET: Metabolism

CYP1A2-inhibitor:	0.05
CYP1A2-substrate:	0.122
CYP2C19-inhibitor:	0.208
CYP2C19-substrate:	0.826
CYP2C9-inhibitor:	0.379
CYP2C9-substrate:	0.258
CYP2D6-inhibitor:	0.017
CYP2D6-substrate:	0.546
CYP3A4-inhibitor:	0.571
CYP3A4-substrate:	0.375

ADMET: Excretion

Clearance (CL):	3.821
Half-life (T1/2):	0.149

ADMET: Toxicity

hERG Blockers:	0.376
Human Hepatotoxicity (H-HT):	0.474
Drug-inuced Liver Injury (DILI):	0.283
AMES Toxicity:	0.041
Rat Oral Acute Toxicity:	0.2
Maximum Recommended Daily Dose:	0.938
Skin Sensitization:	0.924
Carcinogencity:	0.82
Eye Corrosion:	0.352
Eye Irritation:	0.094
Respiratory Toxicity:	0.964

Download Data

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

Natural Product: NPC264546

Natural Product ID:	NPC264546
*Common Name:**	Negundoin C
IUPAC Name:	[(2S,4aS,5R,5'E,6R,8aS)-1,1,4a,6-tetramethyl-5'-(2-oxoethylidene)spiro[3,4,6,7,8,8a-hexahydro-2H-naphthalene-5,2'-oxolane]-2-yl] acetate
Synonyms:	Negundoin C
Standard InCHIKey:	YUIOUOHLEHUTMC-CXDIRSQKSA-N
Standard InCHI:	InChI=1S/C21H32O4/c1-14-6-7-17-19(3,4)18(24-15(2)23)9-11-20(17,5)21(14)12-8-16(25-21)10-13-22/h10,13-14,17-18H,6-9,11-12H2,1-5H3/b16-10+/t14-,17+,18+,20+,21-/m1/s1
SMILES:	O=C/C=C/1CC[C@@]2(O1)[C@H](C)CC[C@@H]1[C@]2(C)CC[C@@H](C1(C)C)OC(=O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL591822
PubChem CID:	46229719
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0002648] Tetrahydrofurans

*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
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	leaves	n.a.	n.a.	PMID[12828478]
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	n.a.	root	n.a.	PMID[15520511]
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	seeds	n.a.	n.a.	PMID[15620254]
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	seeds	n.a.	n.a.	PMID[1624939]
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17027268]
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	Seeds	n.a.	n.a.	PMID[19715321]
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	Seeds	n.a.	n.a.	PMID[19931461]
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23403897]
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO14602	Vitex negundo	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	1
Others	2

Activity Type	# Activity
Cell Line	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	120.0	nM	PMID[565836]
NPT113	Cell Line	RAW264.7	Mus musculus	Inhibition	=	2.06	%	PMID[565836]
NPT113	Cell Line	RAW264.7	Mus musculus	Inhibition	=	0.4	%	PMID[565836]

☑ 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 NPC264546 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	193
0.1-0.2	1379
0.2-0.3	5438
0.3-0.4	14514
0.4-0.5	8232
0.5-0.6	6809
0.6-0.7	5458
0.7-0.8	664
0.8-0.85	6
0.85-0.9	1
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9176	High Similarity	NPC106332
0.907	High Similarity	NPC170633
0.8765	High Similarity	NPC219809
0.8315	Intermediate Similarity	NPC291665
0.8152	Intermediate Similarity	NPC7349
0.8085	Intermediate Similarity	NPC475380
0.8085	Intermediate Similarity	NPC209297
0.8065	Intermediate Similarity	NPC105490
0.8065	Intermediate Similarity	NPC140277
0.8023	Intermediate Similarity	NPC469802
0.8	Intermediate Similarity	NPC311241
0.8	Intermediate Similarity	NPC475446
0.7978	Intermediate Similarity	NPC474013
0.7957	Intermediate Similarity	NPC474185
0.7955	Intermediate Similarity	NPC476927
0.7938	Intermediate Similarity	NPC119467
0.7938	Intermediate Similarity	NPC475767
0.7931	Intermediate Similarity	NPC170303
0.7917	Intermediate Similarity	NPC72647
0.7917	Intermediate Similarity	NPC107806
0.7917	Intermediate Similarity	NPC278673
0.7912	Intermediate Similarity	NPC93411
0.7895	Intermediate Similarity	NPC194132
0.7865	Intermediate Similarity	NPC306951
0.7865	Intermediate Similarity	NPC96055
0.7849	Intermediate Similarity	NPC473675
0.7841	Intermediate Similarity	NPC256112
0.7835	Intermediate Similarity	NPC471413
0.7812	Intermediate Similarity	NPC100912
0.7802	Intermediate Similarity	NPC166857
0.7789	Intermediate Similarity	NPC276110
0.7778	Intermediate Similarity	NPC474575
0.7766	Intermediate Similarity	NPC12297
0.7755	Intermediate Similarity	NPC471412
0.7742	Intermediate Similarity	NPC302280
0.7742	Intermediate Similarity	NPC328141
0.7742	Intermediate Similarity	NPC474842
0.7742	Intermediate Similarity	NPC475965
0.7723	Intermediate Similarity	NPC179380
0.7723	Intermediate Similarity	NPC302788
0.7723	Intermediate Similarity	NPC475074
0.7708	Intermediate Similarity	NPC151725
0.7708	Intermediate Similarity	NPC122324
0.7708	Intermediate Similarity	NPC106425
0.7701	Intermediate Similarity	NPC283789
0.7692	Intermediate Similarity	NPC214315
0.7684	Intermediate Similarity	NPC269729
0.7684	Intermediate Similarity	NPC57117
0.7684	Intermediate Similarity	NPC279410
0.7684	Intermediate Similarity	NPC119562
0.7677	Intermediate Similarity	NPC109195
0.7677	Intermediate Similarity	NPC475038
0.7677	Intermediate Similarity	NPC162973
0.7667	Intermediate Similarity	NPC471367
0.7667	Intermediate Similarity	NPC102048
0.7653	Intermediate Similarity	NPC470906
0.7653	Intermediate Similarity	NPC324841
0.764	Intermediate Similarity	NPC286786
0.764	Intermediate Similarity	NPC471218
0.764	Intermediate Similarity	NPC2524
0.7634	Intermediate Similarity	NPC50070
0.7634	Intermediate Similarity	NPC82876
0.7629	Intermediate Similarity	NPC51499
0.7624	Intermediate Similarity	NPC471206
0.7614	Intermediate Similarity	NPC269791
0.7609	Intermediate Similarity	NPC175293
0.7604	Intermediate Similarity	NPC274417
0.76	Intermediate Similarity	NPC120009
0.76	Intermediate Similarity	NPC120321
0.76	Intermediate Similarity	NPC282233
0.76	Intermediate Similarity	NPC254202
0.76	Intermediate Similarity	NPC95585
0.7579	Intermediate Similarity	NPC473678
0.7579	Intermediate Similarity	NPC38232
0.7576	Intermediate Similarity	NPC268829
0.7576	Intermediate Similarity	NPC247701
0.7576	Intermediate Similarity	NPC25177
0.7576	Intermediate Similarity	NPC222875
0.7576	Intermediate Similarity	NPC11974
0.7576	Intermediate Similarity	NPC295110
0.7556	Intermediate Similarity	NPC139206
0.7556	Intermediate Similarity	NPC132386
0.7556	Intermediate Similarity	NPC473742
0.7553	Intermediate Similarity	NPC78973
0.7551	Intermediate Similarity	NPC275086
0.7551	Intermediate Similarity	NPC325229
0.7551	Intermediate Similarity	NPC218107
0.7528	Intermediate Similarity	NPC195334
0.7528	Intermediate Similarity	NPC290495
0.7527	Intermediate Similarity	NPC470612
0.7527	Intermediate Similarity	NPC470613
0.7527	Intermediate Similarity	NPC80335
0.7526	Intermediate Similarity	NPC8954
0.7526	Intermediate Similarity	NPC16967
0.7526	Intermediate Similarity	NPC29952
0.7526	Intermediate Similarity	NPC471039
0.7526	Intermediate Similarity	NPC94905
0.7525	Intermediate Similarity	NPC165969
0.75	Intermediate Similarity	NPC161998
0.75	Intermediate Similarity	NPC22388
0.75	Intermediate Similarity	NPC474970
0.75	Intermediate Similarity	NPC128488
0.75	Intermediate Similarity	NPC44083
0.75	Intermediate Similarity	NPC175145
0.75	Intermediate Similarity	NPC153987
0.75	Intermediate Similarity	NPC471219
0.75	Intermediate Similarity	NPC475069
0.75	Intermediate Similarity	NPC304968
0.75	Intermediate Similarity	NPC131813
0.75	Intermediate Similarity	NPC103491
0.75	Intermediate Similarity	NPC471040
0.75	Intermediate Similarity	NPC471369
0.7475	Intermediate Similarity	NPC35751
0.7475	Intermediate Similarity	NPC38855
0.7475	Intermediate Similarity	NPC251680
0.7475	Intermediate Similarity	NPC471041
0.7474	Intermediate Similarity	NPC329842
0.7474	Intermediate Similarity	NPC473944
0.7474	Intermediate Similarity	NPC72845
0.7473	Intermediate Similarity	NPC32223
0.7473	Intermediate Similarity	NPC299963
0.7471	Intermediate Similarity	NPC470428
0.7451	Intermediate Similarity	NPC34768
0.7451	Intermediate Similarity	NPC218158
0.7449	Intermediate Similarity	NPC198549
0.7449	Intermediate Similarity	NPC113976
0.7449	Intermediate Similarity	NPC99726
0.7447	Intermediate Similarity	NPC471043
0.7447	Intermediate Similarity	NPC246028
0.7447	Intermediate Similarity	NPC314727
0.7444	Intermediate Similarity	NPC472504
0.7426	Intermediate Similarity	NPC478057
0.7426	Intermediate Similarity	NPC160583
0.7426	Intermediate Similarity	NPC45897
0.7426	Intermediate Similarity	NPC176883
0.7426	Intermediate Similarity	NPC10232
0.7426	Intermediate Similarity	NPC196471
0.7426	Intermediate Similarity	NPC189588
0.7426	Intermediate Similarity	NPC187302
0.7426	Intermediate Similarity	NPC97487
0.7423	Intermediate Similarity	NPC472189
0.7423	Intermediate Similarity	NPC279974
0.7423	Intermediate Similarity	NPC471362
0.7423	Intermediate Similarity	NPC281134
0.7423	Intermediate Similarity	NPC471372
0.7419	Intermediate Similarity	NPC478104
0.7416	Intermediate Similarity	NPC281880
0.74	Intermediate Similarity	NPC472554
0.74	Intermediate Similarity	NPC168319
0.74	Intermediate Similarity	NPC194028
0.7396	Intermediate Similarity	NPC475657
0.7396	Intermediate Similarity	NPC79117
0.7391	Intermediate Similarity	NPC164424
0.7391	Intermediate Similarity	NPC2709
0.7391	Intermediate Similarity	NPC476602
0.7386	Intermediate Similarity	NPC476949
0.7379	Intermediate Similarity	NPC319438
0.7374	Intermediate Similarity	NPC119036
0.7374	Intermediate Similarity	NPC252295
0.7368	Intermediate Similarity	NPC475776
0.7363	Intermediate Similarity	NPC79945
0.7353	Intermediate Similarity	NPC470297
0.7347	Intermediate Similarity	NPC111684
0.7347	Intermediate Similarity	NPC234993
0.7347	Intermediate Similarity	NPC307164
0.7347	Intermediate Similarity	NPC276103
0.7347	Intermediate Similarity	NPC471903
0.7347	Intermediate Similarity	NPC253115
0.7347	Intermediate Similarity	NPC475178
0.7347	Intermediate Similarity	NPC304899
0.7347	Intermediate Similarity	NPC54248
0.7347	Intermediate Similarity	NPC58052
0.7347	Intermediate Similarity	NPC171598
0.7347	Intermediate Similarity	NPC134072
0.734	Intermediate Similarity	NPC224145
0.734	Intermediate Similarity	NPC473879
0.734	Intermediate Similarity	NPC263079
0.734	Intermediate Similarity	NPC473229
0.7333	Intermediate Similarity	NPC474567
0.7333	Intermediate Similarity	NPC108476
0.7333	Intermediate Similarity	NPC475665
0.7333	Intermediate Similarity	NPC159148
0.7333	Intermediate Similarity	NPC25554
0.7333	Intermediate Similarity	NPC142163
0.7333	Intermediate Similarity	NPC476101
0.7327	Intermediate Similarity	NPC472815
0.7327	Intermediate Similarity	NPC476081
0.7327	Intermediate Similarity	NPC472552
0.7327	Intermediate Similarity	NPC11956
0.732	Intermediate Similarity	NPC477722
0.732	Intermediate Similarity	NPC473435
0.732	Intermediate Similarity	NPC471078
0.732	Intermediate Similarity	NPC473431
0.732	Intermediate Similarity	NPC473280
0.732	Intermediate Similarity	NPC201725
0.732	Intermediate Similarity	NPC191521
0.732	Intermediate Similarity	NPC474922
0.7312	Intermediate Similarity	NPC286153
0.7312	Intermediate Similarity	NPC73038
0.7312	Intermediate Similarity	NPC102996

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 NPC264546 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	166
0.1-0.2	1668
0.2-0.3	4318
0.3-0.4	2115
0.4-0.5	478
0.5-0.6	168
0.6-0.7	211
0.7-0.8	26
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
0.7551	Intermediate Similarity	NPD7638	Approved
0.7475	Intermediate Similarity	NPD7639	Approved
0.7475	Intermediate Similarity	NPD7640	Approved
0.7282	Intermediate Similarity	NPD6008	Approved
0.7143	Intermediate Similarity	NPD7748	Approved
0.7143	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7900	Approved
0.7128	Intermediate Similarity	NPD7521	Approved
0.7128	Intermediate Similarity	NPD7334	Approved
0.7128	Intermediate Similarity	NPD6684	Approved
0.7128	Intermediate Similarity	NPD7146	Approved
0.7128	Intermediate Similarity	NPD6409	Approved
0.7128	Intermediate Similarity	NPD5330	Approved
0.7071	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7065	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7053	Intermediate Similarity	NPD3573	Approved
0.703	Intermediate Similarity	NPD4225	Approved
0.6979	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6979	Remote Similarity	NPD6672	Approved
0.6979	Remote Similarity	NPD5737	Approved
0.6979	Remote Similarity	NPD6903	Approved
0.6939	Remote Similarity	NPD7515	Phase 2
0.6931	Remote Similarity	NPD7902	Approved
0.6907	Remote Similarity	NPD6051	Approved
0.6848	Remote Similarity	NPD7525	Registered
0.6842	Remote Similarity	NPD1694	Approved
0.6827	Remote Similarity	NPD7632	Discontinued
0.6822	Remote Similarity	NPD6899	Approved
0.6822	Remote Similarity	NPD6881	Approved
0.6792	Remote Similarity	NPD5739	Approved
0.6792	Remote Similarity	NPD6675	Approved
0.6792	Remote Similarity	NPD7128	Approved
0.6792	Remote Similarity	NPD6402	Approved
0.6735	Remote Similarity	NPD6673	Approved
0.6735	Remote Similarity	NPD6080	Approved
0.6735	Remote Similarity	NPD6904	Approved
0.6729	Remote Similarity	NPD5697	Approved
0.67	Remote Similarity	NPD6399	Phase 3
0.6697	Remote Similarity	NPD6883	Approved
0.6697	Remote Similarity	NPD7290	Approved
0.6697	Remote Similarity	NPD7102	Approved
0.6696	Remote Similarity	NPD7503	Approved
0.6667	Remote Similarity	NPD6011	Approved
0.6667	Remote Similarity	NPD7320	Approved
0.6667	Remote Similarity	NPD4632	Approved
0.6636	Remote Similarity	NPD6617	Approved
0.6636	Remote Similarity	NPD8130	Phase 1
0.6636	Remote Similarity	NPD6869	Approved
0.6636	Remote Similarity	NPD6649	Approved
0.6636	Remote Similarity	NPD6650	Approved
0.6636	Remote Similarity	NPD6847	Approved
0.6635	Remote Similarity	NPD6648	Approved
0.6634	Remote Similarity	NPD6001	Approved
0.6606	Remote Similarity	NPD6014	Approved
0.6606	Remote Similarity	NPD6012	Approved
0.6606	Remote Similarity	NPD6372	Approved
0.6606	Remote Similarity	NPD6013	Approved
0.6606	Remote Similarity	NPD6373	Approved
0.6602	Remote Similarity	NPD6084	Phase 2
0.6602	Remote Similarity	NPD6083	Phase 2
0.66	Remote Similarity	NPD6079	Approved
0.6598	Remote Similarity	NPD3618	Phase 1
0.6579	Remote Similarity	NPD7328	Approved
0.6579	Remote Similarity	NPD7327	Approved
0.6577	Remote Similarity	NPD8297	Approved
0.6577	Remote Similarity	NPD6882	Approved
0.6574	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6574	Remote Similarity	NPD5701	Approved
0.6571	Remote Similarity	NPD5344	Discontinued
0.6566	Remote Similarity	NPD5328	Approved
0.6559	Remote Similarity	NPD7645	Phase 2
0.6525	Remote Similarity	NPD7492	Approved
0.6522	Remote Similarity	NPD7516	Approved
0.6514	Remote Similarity	NPD6686	Approved
0.6505	Remote Similarity	NPD4697	Phase 3
0.6491	Remote Similarity	NPD6009	Approved
0.6486	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD7507	Approved
0.6471	Remote Similarity	NPD6616	Approved
0.6466	Remote Similarity	NPD6319	Approved
0.6466	Remote Similarity	NPD8377	Approved
0.6466	Remote Similarity	NPD6054	Approved
0.6466	Remote Similarity	NPD8294	Approved
0.6465	Remote Similarity	NPD5208	Approved
0.6458	Remote Similarity	NPD6695	Phase 3
0.6455	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6441	Remote Similarity	NPD7604	Phase 2
0.6436	Remote Similarity	NPD8035	Phase 2
0.6436	Remote Similarity	NPD5693	Phase 1
0.6436	Remote Similarity	NPD8034	Phase 2
0.6436	Remote Similarity	NPD6050	Approved
0.6429	Remote Similarity	NPD6098	Approved
0.6417	Remote Similarity	NPD7078	Approved
0.641	Remote Similarity	NPD8296	Approved
0.641	Remote Similarity	NPD8380	Approved
0.641	Remote Similarity	NPD8033	Approved
0.641	Remote Similarity	NPD8335	Approved
0.641	Remote Similarity	NPD8379	Approved
0.641	Remote Similarity	NPD8378	Approved
0.641	Remote Similarity	NPD5983	Phase 2
0.6408	Remote Similarity	NPD5695	Phase 3
0.6396	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6392	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6383	Remote Similarity	NPD4195	Approved
0.6381	Remote Similarity	NPD5696	Approved
0.6373	Remote Similarity	NPD4202	Approved
0.6364	Remote Similarity	NPD7736	Approved
0.6356	Remote Similarity	NPD6370	Approved
0.6348	Remote Similarity	NPD7115	Discovery
0.6346	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6346	Remote Similarity	NPD5222	Approved
0.6346	Remote Similarity	NPD5221	Approved
0.6337	Remote Similarity	NPD5207	Approved
0.6337	Remote Similarity	NPD5692	Phase 3
0.6333	Remote Similarity	NPD6336	Discontinued
0.6327	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6325	Remote Similarity	NPD6059	Approved
0.6321	Remote Similarity	NPD5285	Approved
0.6321	Remote Similarity	NPD4696	Approved
0.6321	Remote Similarity	NPD5286	Approved
0.6311	Remote Similarity	NPD7319	Approved
0.6311	Remote Similarity	NPD5282	Discontinued
0.6304	Remote Similarity	NPD7339	Approved
0.6304	Remote Similarity	NPD6942	Approved
0.6293	Remote Similarity	NPD6335	Approved
0.6286	Remote Similarity	NPD5173	Approved
0.6286	Remote Similarity	NPD4755	Approved
0.6281	Remote Similarity	NPD8293	Discontinued
0.6275	Remote Similarity	NPD7637	Suspended
0.6275	Remote Similarity	NPD5694	Approved
0.6273	Remote Similarity	NPD6412	Phase 2
0.6271	Remote Similarity	NPD6016	Approved
0.6271	Remote Similarity	NPD6015	Approved
0.6263	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6262	Remote Similarity	NPD5223	Approved
0.6261	Remote Similarity	NPD6274	Approved
0.6261	Remote Similarity	NPD6868	Approved
0.6239	Remote Similarity	NPD7101	Approved
0.6239	Remote Similarity	NPD7100	Approved
0.6237	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6224	Remote Similarity	NPD3666	Approved
0.6224	Remote Similarity	NPD3665	Phase 1
0.6224	Remote Similarity	NPD4786	Approved
0.6224	Remote Similarity	NPD3133	Approved
0.6224	Remote Similarity	NPD3668	Phase 3
0.6218	Remote Similarity	NPD5988	Approved
0.6207	Remote Similarity	NPD6317	Approved
0.6204	Remote Similarity	NPD4633	Approved
0.6204	Remote Similarity	NPD5211	Phase 2
0.6204	Remote Similarity	NPD5226	Approved
0.6204	Remote Similarity	NPD5225	Approved
0.6204	Remote Similarity	NPD5224	Approved
0.62	Remote Similarity	NPD7750	Discontinued
0.62	Remote Similarity	NPD7524	Approved
0.6196	Remote Similarity	NPD6924	Approved
0.6196	Remote Similarity	NPD6926	Approved
0.6186	Remote Similarity	NPD3667	Approved
0.6168	Remote Similarity	NPD4700	Approved
0.6154	Remote Similarity	NPD6313	Approved
0.6154	Remote Similarity	NPD6314	Approved
0.6147	Remote Similarity	NPD5175	Approved
0.6147	Remote Similarity	NPD5174	Approved
0.6147	Remote Similarity	NPD6052	Approved
0.6146	Remote Similarity	NPD4695	Discontinued
0.6146	Remote Similarity	NPD6930	Phase 2
0.6146	Remote Similarity	NPD6931	Approved
0.614	Remote Similarity	NPD6053	Discontinued
0.6134	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6106	Remote Similarity	NPD4634	Approved
0.6105	Remote Similarity	NPD6114	Approved
0.6105	Remote Similarity	NPD6697	Approved
0.6105	Remote Similarity	NPD6118	Approved
0.6105	Remote Similarity	NPD6115	Approved
0.6091	Remote Similarity	NPD5141	Approved
0.6078	Remote Similarity	NPD4753	Phase 2
0.6078	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6075	Remote Similarity	NPD5290	Discontinued
0.6071	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6064	Remote Similarity	NPD6933	Approved
0.6042	Remote Similarity	NPD6929	Approved
0.604	Remote Similarity	NPD4251	Approved
0.604	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.604	Remote Similarity	NPD4250	Approved
0.6038	Remote Similarity	NPD7732	Phase 3
0.6038	Remote Similarity	NPD5349	Clinical (unspecified phase)
0.6033	Remote Similarity	NPD6067	Discontinued
0.6033	Remote Similarity	NPD8328	Phase 3
0.6023	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.602	Remote Similarity	NPD4223	Phase 3
0.602	Remote Similarity	NPD4221	Approved
0.6018	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6	Remote Similarity	NPD6908	Approved
0.6	Remote Similarity	NPD6909	Approved
0.6	Remote Similarity	NPD4754	Approved
0.6	Remote Similarity	NPD6932	Approved
0.6	Remote Similarity	NPD5329	Approved
0.5982	Remote Similarity	NPD6614	Approved
0.5979	Remote Similarity	NPD7509	Discontinued
0.5978	Remote Similarity	NPD4243	Approved
0.5968	Remote Similarity	NPD6033	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