NPASS Compound

Structure

NPC106332 OpenBabel07101718182D 27 29 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 -3.7807 -2.2441 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 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 -1.3849 -1.1215 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 -2.3794 -1.2260 0.0000 C 0 0 0 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 4.4347 0.4945 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.9672 -0.4170 0.0000 O 0 0 0 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 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 20 1 0 0 0 0 4 20 1 0 0 0 0 5 21 1 0 0 0 0 6 25 1 0 0 0 0 7 8 1 0 0 0 0 7 14 1 0 0 0 0 8 17 1 0 0 0 0 9 12 1 0 0 0 0 9 16 1 0 0 0 0 10 11 1 0 0 0 0 10 18 1 0 0 0 0 11 21 1 0 0 0 0 13 16 2 0 0 0 0 13 19 1 0 0 0 0 14 22 1 6 0 0 0 15 23 2 0 0 0 0 15 26 1 0 0 0 0 16 27 1 0 0 0 0 17 20 1 0 0 0 0 17 21 1 1 0 0 0 18 20 1 0 0 0 0 18 26 1 1 0 0 0 19 24 2 0 0 0 0 19 25 1 0 0 0 0 21 22 1 6 0 0 0 22 12 1 1 0 0 0 22 27 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	378.24
Volume:	399.441
LogP:	4.357
LogD:	3.586
LogS:	-4.534
# Rotatable Bonds:	4
TPSA:	61.83
# H-Bond Aceptor:	5
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.526
Synthetic Accessibility Score:	4.88
Fsp3:	0.818
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.69
MDCK Permeability:	2.3699109078734182e-05
Pgp-inhibitor:	0.998
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.957
30% Bioavailability (F30%):	0.922

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.246
Plasma Protein Binding (PPB):	84.48207092285156%
Volume Distribution (VD):	1.44
Pgp-substrate:	18.332788467407227%

ADMET: Metabolism

CYP1A2-inhibitor:	0.05
CYP1A2-substrate:	0.162
CYP2C19-inhibitor:	0.567
CYP2C19-substrate:	0.859
CYP2C9-inhibitor:	0.74
CYP2C9-substrate:	0.09
CYP2D6-inhibitor:	0.022
CYP2D6-substrate:	0.198
CYP3A4-inhibitor:	0.775
CYP3A4-substrate:	0.559

ADMET: Excretion

Clearance (CL):	4.822
Half-life (T1/2):	0.172

ADMET: Toxicity

hERG Blockers:	0.351
Human Hepatotoxicity (H-HT):	0.84
Drug-inuced Liver Injury (DILI):	0.397
AMES Toxicity:	0.005
Rat Oral Acute Toxicity:	0.052
Maximum Recommended Daily Dose:	0.952
Skin Sensitization:	0.952
Carcinogencity:	0.105
Eye Corrosion:	0.119
Eye Irritation:	0.087
Respiratory Toxicity:	0.956

Download Data

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

Natural Product: NPC106332

Natural Product ID:	NPC106332
*Common Name:**	Negundoin A
IUPAC Name:	methyl (2E)-2-[(3S,4aS,7R,8R,8aS)-3-acetyloxy-4,4,7,8a-tetramethylspiro[2,3,4a,5,6,7-hexahydro-1H-naphthalene-8,5'-oxolane]-2'-ylidene]acetate
Synonyms:
Standard InCHIKey:	IFXOQBCVGIFCLI-VSSSNARASA-N
Standard InCHI:	InChI=1S/C22H34O5/c1-14-7-8-17-20(3,4)18(26-15(2)23)10-11-21(17,5)22(14)12-9-16(27-22)13-19(24)25-6/h13-14,17-18H,7-12H2,1-6H3/b16-13+/t14-,17+,18+,21+,22-/m1/s1
SMILES:	COC(=O)/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:	CHEMBL589343
PubChem CID:	46229707
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000264] Organic acids and derivatives [CHEMONTID:0000265] Carboxylic acids and derivatives [CHEMONTID:0000346] Dicarboxylic acids and derivatives

*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	1

Activity Type	# Activity
Cell Line	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	9830.0	nM	PMID[569838]
NPT113	Cell Line	RAW264.7	Mus musculus	Inhibition	=	68.21	%	PMID[569838]

☑ 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 NPC106332 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	192
0.1-0.2	1370
0.2-0.3	4721
0.3-0.4	10719
0.4-0.5	11476
0.5-0.6	7451
0.6-0.7	5503
0.7-0.8	1175
0.8-0.85	76
0.85-0.9	11
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9412	High Similarity	NPC170633
0.9176	High Similarity	NPC264546
0.8876	High Similarity	NPC7349
0.8795	High Similarity	NPC469802
0.8778	High Similarity	NPC140277
0.8778	High Similarity	NPC105490
0.8721	High Similarity	NPC474013
0.8636	High Similarity	NPC93411
0.8605	High Similarity	NPC96055
0.8602	High Similarity	NPC278673
0.8587	High Similarity	NPC209297
0.8587	High Similarity	NPC194132
0.8587	High Similarity	NPC475380
0.8523	High Similarity	NPC166857
0.8495	Intermediate Similarity	NPC311241
0.8495	Intermediate Similarity	NPC475446
0.8495	Intermediate Similarity	NPC100912
0.8478	Intermediate Similarity	NPC276110
0.8404	Intermediate Similarity	NPC72647
0.8404	Intermediate Similarity	NPC107806
0.8372	Intermediate Similarity	NPC471218
0.8367	Intermediate Similarity	NPC302788
0.8367	Intermediate Similarity	NPC475074
0.8316	Intermediate Similarity	NPC324841
0.8316	Intermediate Similarity	NPC471413
0.8298	Intermediate Similarity	NPC51499
0.8276	Intermediate Similarity	NPC476927
0.8265	Intermediate Similarity	NPC471206
0.8256	Intermediate Similarity	NPC170303
0.8247	Intermediate Similarity	NPC120009
0.8242	Intermediate Similarity	NPC302280
0.8242	Intermediate Similarity	NPC78973
0.8229	Intermediate Similarity	NPC295110
0.8229	Intermediate Similarity	NPC222875
0.8229	Intermediate Similarity	NPC471412
0.8229	Intermediate Similarity	NPC268829
0.8229	Intermediate Similarity	NPC25177
0.8229	Intermediate Similarity	NPC11974
0.8229	Intermediate Similarity	NPC247701
0.8211	Intermediate Similarity	NPC325229
0.8211	Intermediate Similarity	NPC275086
0.8202	Intermediate Similarity	NPC131813
0.8202	Intermediate Similarity	NPC471219
0.8191	Intermediate Similarity	NPC8954
0.8191	Intermediate Similarity	NPC94905
0.8182	Intermediate Similarity	NPC32223
0.8182	Intermediate Similarity	NPC306951
0.8172	Intermediate Similarity	NPC57117
0.8172	Intermediate Similarity	NPC161998
0.8161	Intermediate Similarity	NPC256112
0.8152	Intermediate Similarity	NPC329842
0.8144	Intermediate Similarity	NPC109195
0.8144	Intermediate Similarity	NPC162973
0.8144	Intermediate Similarity	NPC475038
0.8132	Intermediate Similarity	NPC82876
0.8132	Intermediate Similarity	NPC246028
0.8125	Intermediate Similarity	NPC251680
0.8125	Intermediate Similarity	NPC38855
0.8085	Intermediate Similarity	NPC471362
0.8085	Intermediate Similarity	NPC472189
0.8085	Intermediate Similarity	NPC471372
0.8081	Intermediate Similarity	NPC34768
0.8061	Intermediate Similarity	NPC97487
0.8061	Intermediate Similarity	NPC45897
0.8061	Intermediate Similarity	NPC254202
0.8061	Intermediate Similarity	NPC10232
0.8061	Intermediate Similarity	NPC196471
0.8061	Intermediate Similarity	NPC187302
0.8061	Intermediate Similarity	NPC160583
0.8061	Intermediate Similarity	NPC189588
0.8046	Intermediate Similarity	NPC25554
0.8041	Intermediate Similarity	NPC472554
0.8022	Intermediate Similarity	NPC473879
0.8021	Intermediate Similarity	NPC218107
0.8	Intermediate Similarity	NPC16967
0.8	Intermediate Similarity	NPC219809
0.8	Intermediate Similarity	NPC171598
0.8	Intermediate Similarity	NPC29952
0.8	Intermediate Similarity	NPC179380
0.8	Intermediate Similarity	NPC102996
0.8	Intermediate Similarity	NPC189206
0.7979	Intermediate Similarity	NPC477722
0.7978	Intermediate Similarity	NPC102048
0.7978	Intermediate Similarity	NPC318515
0.7959	Intermediate Similarity	NPC472815
0.7959	Intermediate Similarity	NPC476081
0.7959	Intermediate Similarity	NPC11956
0.7959	Intermediate Similarity	NPC472552
0.7957	Intermediate Similarity	NPC473675
0.7957	Intermediate Similarity	NPC234335
0.7957	Intermediate Similarity	NPC473944
0.7957	Intermediate Similarity	NPC72845
0.7955	Intermediate Similarity	NPC2524
0.7941	Intermediate Similarity	NPC103491
0.7938	Intermediate Similarity	NPC228251
0.7938	Intermediate Similarity	NPC16601
0.7938	Intermediate Similarity	NPC54705
0.7938	Intermediate Similarity	NPC161527
0.7938	Intermediate Similarity	NPC477968
0.7938	Intermediate Similarity	NPC219285
0.7938	Intermediate Similarity	NPC477972
0.7938	Intermediate Similarity	NPC477971
0.7938	Intermediate Similarity	NPC20113
0.7921	Intermediate Similarity	NPC38948
0.7921	Intermediate Similarity	NPC50124
0.7917	Intermediate Similarity	NPC472188
0.7912	Intermediate Similarity	NPC102640
0.7912	Intermediate Similarity	NPC175293
0.79	Intermediate Similarity	NPC218158
0.79	Intermediate Similarity	NPC220217
0.79	Intermediate Similarity	NPC119855
0.79	Intermediate Similarity	NPC51719
0.79	Intermediate Similarity	NPC186668
0.7895	Intermediate Similarity	NPC281134
0.7895	Intermediate Similarity	NPC472441
0.7889	Intermediate Similarity	NPC472442
0.7879	Intermediate Similarity	NPC281378
0.7879	Intermediate Similarity	NPC23584
0.7879	Intermediate Similarity	NPC120321
0.7879	Intermediate Similarity	NPC472821
0.7872	Intermediate Similarity	NPC53555
0.7872	Intermediate Similarity	NPC475657
0.7857	Intermediate Similarity	NPC168319
0.7857	Intermediate Similarity	NPC194028
0.7843	Intermediate Similarity	NPC206618
0.7835	Intermediate Similarity	NPC471366
0.7835	Intermediate Similarity	NPC472186
0.7835	Intermediate Similarity	NPC476800
0.7835	Intermediate Similarity	NPC318917
0.7826	Intermediate Similarity	NPC69713
0.7826	Intermediate Similarity	NPC291665
0.7822	Intermediate Similarity	NPC319438
0.7822	Intermediate Similarity	NPC471205
0.7822	Intermediate Similarity	NPC216636
0.7812	Intermediate Similarity	NPC260796
0.7812	Intermediate Similarity	NPC134072
0.7812	Intermediate Similarity	NPC234993
0.7802	Intermediate Similarity	NPC286153
0.7802	Intermediate Similarity	NPC175145
0.7802	Intermediate Similarity	NPC475069
0.78	Intermediate Similarity	NPC165969
0.7789	Intermediate Similarity	NPC279410
0.7789	Intermediate Similarity	NPC191521
0.7789	Intermediate Similarity	NPC119562
0.7789	Intermediate Similarity	NPC201725
0.7766	Intermediate Similarity	NPC49420
0.7766	Intermediate Similarity	NPC177641
0.7766	Intermediate Similarity	NPC472811
0.7766	Intermediate Similarity	NPC78594
0.7766	Intermediate Similarity	NPC477574
0.7755	Intermediate Similarity	NPC473204
0.7755	Intermediate Similarity	NPC472187
0.7755	Intermediate Similarity	NPC473545
0.7755	Intermediate Similarity	NPC47024
0.7753	Intermediate Similarity	NPC155521
0.7745	Intermediate Similarity	NPC189075
0.7745	Intermediate Similarity	NPC137462
0.7745	Intermediate Similarity	NPC275539
0.7745	Intermediate Similarity	NPC304276
0.7742	Intermediate Similarity	NPC50488
0.7742	Intermediate Similarity	NPC177141
0.7742	Intermediate Similarity	NPC261320
0.7742	Intermediate Similarity	NPC474396
0.7732	Intermediate Similarity	NPC73911
0.7732	Intermediate Similarity	NPC110937
0.7732	Intermediate Similarity	NPC10057
0.7727	Intermediate Similarity	NPC233332
0.7727	Intermediate Similarity	NPC281880
0.7723	Intermediate Similarity	NPC478208
0.7723	Intermediate Similarity	NPC172867
0.7717	Intermediate Similarity	NPC476948
0.7717	Intermediate Similarity	NPC471796
0.7714	Intermediate Similarity	NPC171126
0.7708	Intermediate Similarity	NPC474909
0.7708	Intermediate Similarity	NPC476720
0.7708	Intermediate Similarity	NPC476519
0.7701	Intermediate Similarity	NPC184737
0.77	Intermediate Similarity	NPC473523
0.77	Intermediate Similarity	NPC36688
0.77	Intermediate Similarity	NPC171014
0.77	Intermediate Similarity	NPC471938
0.7692	Intermediate Similarity	NPC253604
0.7692	Intermediate Similarity	NPC35933
0.7684	Intermediate Similarity	NPC12297
0.7684	Intermediate Similarity	NPC472812
0.7684	Intermediate Similarity	NPC472641
0.7684	Intermediate Similarity	NPC163902
0.7684	Intermediate Similarity	NPC38232
0.7684	Intermediate Similarity	NPC110022
0.7684	Intermediate Similarity	NPC472640
0.7684	Intermediate Similarity	NPC139692
0.7684	Intermediate Similarity	NPC205034
0.7684	Intermediate Similarity	NPC152778
0.7684	Intermediate Similarity	NPC162615
0.7677	Intermediate Similarity	NPC475617
0.7677	Intermediate Similarity	NPC475767
0.7677	Intermediate Similarity	NPC119467
0.767	Intermediate Similarity	NPC322912
0.767	Intermediate Similarity	NPC112457
0.767	Intermediate Similarity	NPC475030

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 NPC106332 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	162
0.1-0.2	1553
0.2-0.3	4045
0.3-0.4	2295
0.4-0.5	665
0.5-0.6	203
0.6-0.7	204
0.7-0.8	20
0.8-0.85	3
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8211	Intermediate Similarity	NPD7638	Approved
0.8125	Intermediate Similarity	NPD7640	Approved
0.8125	Intermediate Similarity	NPD7639	Approved
0.7556	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7553	Intermediate Similarity	NPD6051	Approved
0.7475	Intermediate Similarity	NPD4225	Approved
0.7426	Intermediate Similarity	NPD7632	Discontinued
0.7312	Intermediate Similarity	NPD1694	Approved
0.7212	Intermediate Similarity	NPD6008	Approved
0.7143	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.7117	Intermediate Similarity	NPD7327	Approved
0.7117	Intermediate Similarity	NPD7328	Approved
0.708	Intermediate Similarity	NPD7503	Approved
0.7071	Intermediate Similarity	NPD7748	Approved
0.7071	Intermediate Similarity	NPD7900	Approved
0.7071	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD6648	Approved
0.7054	Intermediate Similarity	NPD7516	Approved
0.7053	Intermediate Similarity	NPD6684	Approved
0.7053	Intermediate Similarity	NPD5330	Approved
0.7053	Intermediate Similarity	NPD6409	Approved
0.7053	Intermediate Similarity	NPD7146	Approved
0.7053	Intermediate Similarity	NPD7521	Approved
0.7053	Intermediate Similarity	NPD7334	Approved
0.7009	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.6991	Remote Similarity	NPD8377	Approved
0.6991	Remote Similarity	NPD8294	Approved
0.699	Remote Similarity	NPD5344	Discontinued
0.6944	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.693	Remote Similarity	NPD8335	Approved
0.693	Remote Similarity	NPD8379	Approved
0.693	Remote Similarity	NPD8378	Approved
0.693	Remote Similarity	NPD8296	Approved
0.693	Remote Similarity	NPD8033	Approved
0.693	Remote Similarity	NPD8380	Approved
0.6916	Remote Similarity	NPD6686	Approved
0.6907	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6907	Remote Similarity	NPD5737	Approved
0.6907	Remote Similarity	NPD6672	Approved
0.6907	Remote Similarity	NPD6903	Approved
0.6869	Remote Similarity	NPD5693	Phase 1
0.6869	Remote Similarity	NPD7515	Phase 2
0.6863	Remote Similarity	NPD7902	Approved
0.6804	Remote Similarity	NPD3573	Approved
0.6774	Remote Similarity	NPD7525	Registered
0.6729	Remote Similarity	NPD6402	Approved
0.6729	Remote Similarity	NPD7128	Approved
0.6729	Remote Similarity	NPD5739	Approved
0.6729	Remote Similarity	NPD6675	Approved
0.6726	Remote Similarity	NPD7115	Discovery
0.6706	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6695	Remote Similarity	NPD7507	Approved
0.6667	Remote Similarity	NPD6080	Approved
0.6667	Remote Similarity	NPD6904	Approved
0.6667	Remote Similarity	NPD6053	Discontinued
0.6667	Remote Similarity	NPD6673	Approved
0.6634	Remote Similarity	NPD6399	Phase 3
0.6606	Remote Similarity	NPD7320	Approved
0.6606	Remote Similarity	NPD6899	Approved
0.6606	Remote Similarity	NPD6881	Approved
0.6569	Remote Similarity	NPD6001	Approved
0.6562	Remote Similarity	NPD6695	Phase 3
0.6545	Remote Similarity	NPD6373	Approved
0.6545	Remote Similarity	NPD6372	Approved
0.6538	Remote Similarity	NPD6084	Phase 2
0.6538	Remote Similarity	NPD6083	Phase 2
0.6535	Remote Similarity	NPD7637	Suspended
0.6531	Remote Similarity	NPD3618	Phase 1
0.6529	Remote Similarity	NPD7319	Approved
0.6514	Remote Similarity	NPD5697	Approved
0.6514	Remote Similarity	NPD5701	Approved
0.65	Remote Similarity	NPD5328	Approved
0.6495	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6495	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6489	Remote Similarity	NPD7645	Phase 2
0.6486	Remote Similarity	NPD7102	Approved
0.6486	Remote Similarity	NPD7290	Approved
0.6486	Remote Similarity	NPD6883	Approved
0.646	Remote Similarity	NPD4632	Approved
0.6455	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6455	Remote Similarity	NPD6011	Approved
0.6429	Remote Similarity	NPD6617	Approved
0.6429	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD8130	Phase 1
0.6429	Remote Similarity	NPD6650	Approved
0.6429	Remote Similarity	NPD6649	Approved
0.6429	Remote Similarity	NPD6869	Approved
0.6429	Remote Similarity	NPD6847	Approved
0.64	Remote Similarity	NPD5208	Approved
0.6396	Remote Similarity	NPD6014	Approved
0.6396	Remote Similarity	NPD6012	Approved
0.6396	Remote Similarity	NPD6013	Approved
0.6373	Remote Similarity	NPD8034	Phase 2
0.6373	Remote Similarity	NPD6050	Approved
0.6373	Remote Similarity	NPD8035	Phase 2
0.6373	Remote Similarity	NPD6079	Approved
0.6372	Remote Similarity	NPD6882	Approved
0.6372	Remote Similarity	NPD8297	Approved
0.6364	Remote Similarity	NPD6098	Approved
0.6346	Remote Similarity	NPD5695	Phase 3
0.6333	Remote Similarity	NPD7492	Approved
0.6321	Remote Similarity	NPD5696	Approved
0.6311	Remote Similarity	NPD4202	Approved
0.63	Remote Similarity	NPD4251	Approved
0.63	Remote Similarity	NPD4250	Approved
0.63	Remote Similarity	NPD7524	Approved
0.63	Remote Similarity	NPD7750	Discontinued
0.63	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6293	Remote Similarity	NPD6009	Approved
0.6289	Remote Similarity	NPD5209	Approved
0.6281	Remote Similarity	NPD6616	Approved
0.6275	Remote Similarity	NPD6698	Approved
0.6275	Remote Similarity	NPD46	Approved
0.6275	Remote Similarity	NPD5692	Phase 3
0.6275	Remote Similarity	NPD5207	Approved
0.6275	Remote Similarity	NPD7838	Discovery
0.6271	Remote Similarity	NPD6054	Approved
0.6271	Remote Similarity	NPD6059	Approved
0.6271	Remote Similarity	NPD6319	Approved
0.6263	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.625	Remote Similarity	NPD5282	Discontinued
0.625	Remote Similarity	NPD6930	Phase 2
0.625	Remote Similarity	NPD7604	Phase 2
0.625	Remote Similarity	NPD6931	Approved
0.6237	Remote Similarity	NPD6942	Approved
0.6237	Remote Similarity	NPD7339	Approved
0.6237	Remote Similarity	NPD8039	Approved
0.623	Remote Similarity	NPD8293	Discontinued
0.623	Remote Similarity	NPD7078	Approved
0.6226	Remote Similarity	NPD4755	Approved
0.6218	Remote Similarity	NPD5983	Phase 2
0.6216	Remote Similarity	NPD6412	Phase 2
0.6214	Remote Similarity	NPD5694	Approved
0.6207	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.62	Remote Similarity	NPD4249	Approved
0.6179	Remote Similarity	NPD7736	Approved
0.6176	Remote Similarity	NPD1695	Approved
0.6174	Remote Similarity	NPD8133	Approved
0.617	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6168	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6167	Remote Similarity	NPD6370	Approved
0.6162	Remote Similarity	NPD3133	Approved
0.6162	Remote Similarity	NPD4786	Approved
0.6162	Remote Similarity	NPD3665	Phase 1
0.6162	Remote Similarity	NPD3668	Phase 3
0.6162	Remote Similarity	NPD3666	Approved
0.6154	Remote Similarity	NPD5778	Approved
0.6154	Remote Similarity	NPD5779	Approved
0.6148	Remote Similarity	NPD6336	Discontinued
0.6147	Remote Similarity	NPD5211	Phase 2
0.6146	Remote Similarity	NPD4195	Approved
0.6146	Remote Similarity	NPD6929	Approved
0.6132	Remote Similarity	NPD5222	Approved
0.6132	Remote Similarity	NPD4697	Phase 3
0.6132	Remote Similarity	NPD5221	Approved
0.6132	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6129	Remote Similarity	NPD6924	Approved
0.6129	Remote Similarity	NPD6926	Approved
0.6122	Remote Similarity	NPD3667	Approved
0.6117	Remote Similarity	NPD5785	Approved
0.6111	Remote Similarity	NPD4700	Approved
0.6111	Remote Similarity	NPD5286	Approved
0.6111	Remote Similarity	NPD4696	Approved
0.6111	Remote Similarity	NPD5285	Approved
0.6102	Remote Similarity	NPD6335	Approved
0.61	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6091	Remote Similarity	NPD6052	Approved
0.6083	Remote Similarity	NPD6016	Approved
0.6083	Remote Similarity	NPD6015	Approved
0.6082	Remote Similarity	NPD7514	Phase 3
0.6082	Remote Similarity	NPD7332	Phase 2
0.6075	Remote Similarity	NPD5173	Approved
0.6071	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6068	Remote Similarity	NPD6274	Approved
0.6068	Remote Similarity	NPD6868	Approved
0.6058	Remote Similarity	NPD7087	Discontinued
0.6055	Remote Similarity	NPD5223	Approved
0.6053	Remote Similarity	NPD6371	Approved
0.605	Remote Similarity	NPD7101	Approved
0.605	Remote Similarity	NPD7100	Approved
0.6042	Remote Similarity	NPD6118	Approved
0.6042	Remote Similarity	NPD6114	Approved
0.6042	Remote Similarity	NPD6115	Approved
0.6042	Remote Similarity	NPD6697	Approved
0.604	Remote Similarity	NPD4519	Discontinued
0.604	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.604	Remote Similarity	NPD4623	Approved
0.6036	Remote Similarity	NPD5141	Approved
0.6033	Remote Similarity	NPD5988	Approved
0.6019	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6019	Remote Similarity	NPD4753	Phase 2
0.6017	Remote Similarity	NPD6317	Approved
0.6	Remote Similarity	NPD5226	Approved
0.6	Remote Similarity	NPD4633	Approved
0.6	Remote Similarity	NPD5225	Approved
0.6	Remote Similarity	NPD6933	Approved
0.6	Remote Similarity	NPD5224	Approved
0.5984	Remote Similarity	NPD6067	Discontinued
0.5984	Remote Similarity	NPD8328	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