NPASS Compound

Structure

NPC302788 OpenBabel07101718322D 30 33 0 0 1 0 0 0 0 0999 V2000 5.2812 2.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.0007 2.6939 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5689 2.4684 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8289 2.1775 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1831 -0.5570 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7888 2.8528 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1472 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4152 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0132 1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5491 1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5543 2.5785 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0971 2.4253 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.4619 0.9726 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 -0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2812 1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.7928 1.7158 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.8793 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 1 0 0 0 0 0 0 0 0 0 2.6831 1.3090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 8.9619 0.1066 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 1.3090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.5878 0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 1.8090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 1.6180 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.6831 0.3090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 9.3687 -0.8070 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5878 0.8090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.6831 0.3090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.9838 0.3145 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 15 1 0 0 0 0 2 16 1 0 0 0 0 6 11 1 0 0 0 0 6 12 1 0 0 0 0 7 9 1 0 0 0 0 7 15 2 0 0 0 0 8 10 1 0 0 0 0 8 15 1 0 0 0 0 9 17 2 0 0 0 0 10 19 1 0 0 0 0 11 23 1 0 0 0 0 12 24 1 0 0 0 0 13 16 2 0 0 0 0 13 20 1 0 0 0 0 14 25 1 0 0 0 0 16 17 1 0 0 0 0 17 29 1 0 0 0 0 18 14 1 6 0 0 0 18 21 1 0 0 0 0 18 30 1 0 0 0 0 19 23 1 1 0 0 0 19 25 1 0 0 0 0 20 26 2 0 0 0 0 20 29 1 0 0 0 0 21 23 1 1 0 0 0 21 24 1 0 0 0 0 22 24 1 0 0 0 0 22 27 2 0 0 0 0 22 30 1 0 0 0 0 23 3 1 1 0 0 0 24 4 1 1 0 0 0 25 5 1 1 0 0 0 25 28 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	414.24
Volume:	437.499
LogP:	4.111
LogD:	3.73
LogS:	-4.898
# Rotatable Bonds:	4
TPSA:	79.9
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.738
Synthetic Accessibility Score:	5.307
Fsp3:	0.64
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:	-5.092
MDCK Permeability:	2.1988083972246386e-05
Pgp-inhibitor:	0.002
Pgp-substrate:	0.006
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.265

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.056
Plasma Protein Binding (PPB):	96.61002349853516%
Volume Distribution (VD):	0.957
Pgp-substrate:	4.533810615539551%

ADMET: Metabolism

CYP1A2-inhibitor:	0.038
CYP1A2-substrate:	0.407
CYP2C19-inhibitor:	0.122
CYP2C19-substrate:	0.786
CYP2C9-inhibitor:	0.209
CYP2C9-substrate:	0.565
CYP2D6-inhibitor:	0.391
CYP2D6-substrate:	0.278
CYP3A4-inhibitor:	0.604
CYP3A4-substrate:	0.305

ADMET: Excretion

Clearance (CL):	8.349
Half-life (T1/2):	0.384

ADMET: Toxicity

hERG Blockers:	0.065
Human Hepatotoxicity (H-HT):	0.983
Drug-inuced Liver Injury (DILI):	0.936
AMES Toxicity:	0.215
Rat Oral Acute Toxicity:	0.887
Maximum Recommended Daily Dose:	0.917
Skin Sensitization:	0.583
Carcinogencity:	0.691
Eye Corrosion:	0.005
Eye Irritation:	0.012
Respiratory Toxicity:	0.961

Download Data

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

Natural Product: NPC302788

Natural Product ID:	NPC302788
*Common Name:**	CXKPEHTZBXOOPO-FLUHJTKMSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	CXKPEHTZBXOOPO-FLUHJTKMSA-N
Standard InCHI:	InChI=1S/C25H34O5/c1-15(7-9-17-16(2)13-20(26)29-17)8-10-19-23(3)11-6-12-24(4)21(23)18(30-22(24)27)14-25(19,5)28/h7,9,13,18-19,21,28H,6,8,10-12,14H2,1-5H3/b15-7+,17-9-/t18-,19+,21+,23+,24+,25+/m0/s1
SMILES:	C/C(=CC=C/1C(=CC(=O)O1)C)/CC[C@@H]1[C@@]2(C)CCC[C@]3(C)[C@@H]2[C@H](C[C@@]1(C)O)OC3=O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL496195
PubChem CID:	44157614
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene 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
NPO33075	salvia dominica	Species	Lamiaceae	Eukaryota	aerial parts	n.a.	n.a.	PMID[19459643]

☑ 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
Kd	1

Activity Type	# Activity
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT6478	Individual Protein	Tubulin--tyrosine ligase	Homo sapiens	Kd	=	150.0	nM	PMID[547793]

☑ 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 NPC302788 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	1035
0.2-0.3	3503
0.3-0.4	6177
0.4-0.5	13699
0.5-0.6	8015
0.6-0.7	7277
0.7-0.8	2617
0.8-0.85	165
0.85-0.9	12
0.9-0.95	2
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.95	High Similarity	NPC34768
0.9406	High Similarity	NPC179380
0.901	High Similarity	NPC476081
0.8922	High Similarity	NPC120321
0.89	High Similarity	NPC278673
0.8846	High Similarity	NPC475074
0.8812	High Similarity	NPC471413
0.8725	High Similarity	NPC471412
0.8667	High Similarity	NPC187435
0.8667	High Similarity	NPC67321
0.8641	High Similarity	NPC162973
0.8627	High Similarity	NPC47024
0.8598	High Similarity	NPC478209
0.8585	High Similarity	NPC306265
0.8571	High Similarity	NPC478208
0.8571	High Similarity	NPC471206
0.8515	High Similarity	NPC29952
0.8515	High Similarity	NPC234993
0.8515	High Similarity	NPC134072
0.8462	Intermediate Similarity	NPC469606
0.8462	Intermediate Similarity	NPC31058
0.8462	Intermediate Similarity	NPC273005
0.8462	Intermediate Similarity	NPC58329
0.8447	Intermediate Similarity	NPC54705
0.8426	Intermediate Similarity	NPC472666
0.8416	Intermediate Similarity	NPC276110
0.84	Intermediate Similarity	NPC139692
0.84	Intermediate Similarity	NPC7349
0.8396	Intermediate Similarity	NPC469607
0.8396	Intermediate Similarity	NPC266570
0.8381	Intermediate Similarity	NPC112009
0.8381	Intermediate Similarity	NPC120009
0.8381	Intermediate Similarity	NPC23584
0.8381	Intermediate Similarity	NPC36688
0.8381	Intermediate Similarity	NPC180204
0.8381	Intermediate Similarity	NPC45897
0.8367	Intermediate Similarity	NPC106332
0.8364	Intermediate Similarity	NPC474271
0.8364	Intermediate Similarity	NPC478212
0.835	Intermediate Similarity	NPC216478
0.8333	Intermediate Similarity	NPC473964
0.8333	Intermediate Similarity	NPC478210
0.8333	Intermediate Similarity	NPC16967
0.8317	Intermediate Similarity	NPC105490
0.8291	Intermediate Similarity	NPC476008
0.8286	Intermediate Similarity	NPC155332
0.8286	Intermediate Similarity	NPC165250
0.8286	Intermediate Similarity	NPC114540
0.8286	Intermediate Similarity	NPC32577
0.8286	Intermediate Similarity	NPC11956
0.8283	Intermediate Similarity	NPC170633
0.8273	Intermediate Similarity	NPC470063
0.8269	Intermediate Similarity	NPC473219
0.8269	Intermediate Similarity	NPC470761
0.8257	Intermediate Similarity	NPC478211
0.8252	Intermediate Similarity	NPC473963
0.8252	Intermediate Similarity	NPC51499
0.8246	Intermediate Similarity	NPC41123
0.8246	Intermediate Similarity	NPC145074
0.8246	Intermediate Similarity	NPC114939
0.8241	Intermediate Similarity	NPC50124
0.8241	Intermediate Similarity	NPC275539
0.8241	Intermediate Similarity	NPC189075
0.8235	Intermediate Similarity	NPC157686
0.8235	Intermediate Similarity	NPC259042
0.823	Intermediate Similarity	NPC146786
0.8224	Intermediate Similarity	NPC478052
0.8218	Intermediate Similarity	NPC475657
0.8214	Intermediate Similarity	NPC72772
0.8214	Intermediate Similarity	NPC469794
0.8208	Intermediate Similarity	NPC189588
0.8208	Intermediate Similarity	NPC187302
0.8208	Intermediate Similarity	NPC97487
0.8208	Intermediate Similarity	NPC10232
0.8208	Intermediate Similarity	NPC196471
0.8208	Intermediate Similarity	NPC473283
0.8208	Intermediate Similarity	NPC329345
0.8208	Intermediate Similarity	NPC475526
0.8208	Intermediate Similarity	NPC478057
0.8205	Intermediate Similarity	NPC477745
0.8198	Intermediate Similarity	NPC471204
0.8182	Intermediate Similarity	NPC100329
0.8182	Intermediate Similarity	NPC474846
0.8182	Intermediate Similarity	NPC469656
0.8182	Intermediate Similarity	NPC247031
0.8182	Intermediate Similarity	NPC97939
0.8182	Intermediate Similarity	NPC132790
0.8182	Intermediate Similarity	NPC469655
0.8173	Intermediate Similarity	NPC108368
0.8173	Intermediate Similarity	NPC325229
0.8173	Intermediate Similarity	NPC275086
0.8173	Intermediate Similarity	NPC57079
0.8155	Intermediate Similarity	NPC202833
0.8155	Intermediate Similarity	NPC93245
0.8155	Intermediate Similarity	NPC242848
0.8148	Intermediate Similarity	NPC110496
0.8142	Intermediate Similarity	NPC478204
0.8137	Intermediate Similarity	NPC225474
0.8137	Intermediate Similarity	NPC469596
0.8137	Intermediate Similarity	NPC148000
0.8137	Intermediate Similarity	NPC57117
0.8137	Intermediate Similarity	NPC191521
0.8119	Intermediate Similarity	NPC473944
0.8119	Intermediate Similarity	NPC72845
0.8113	Intermediate Similarity	NPC472552
0.8113	Intermediate Similarity	NPC475038
0.8113	Intermediate Similarity	NPC109195
0.8113	Intermediate Similarity	NPC476769
0.8108	Intermediate Similarity	NPC269530
0.81	Intermediate Similarity	NPC174342
0.8095	Intermediate Similarity	NPC201406
0.8095	Intermediate Similarity	NPC16601
0.8095	Intermediate Similarity	NPC476767
0.8095	Intermediate Similarity	NPC476303
0.8095	Intermediate Similarity	NPC38855
0.8095	Intermediate Similarity	NPC251680
0.8091	Intermediate Similarity	NPC179642
0.8091	Intermediate Similarity	NPC16270
0.8077	Intermediate Similarity	NPC91695
0.8077	Intermediate Similarity	NPC100912
0.8077	Intermediate Similarity	NPC70145
0.8077	Intermediate Similarity	NPC110937
0.8073	Intermediate Similarity	NPC473482
0.8073	Intermediate Similarity	NPC475418
0.8073	Intermediate Similarity	NPC38948
0.8073	Intermediate Similarity	NPC318363
0.807	Intermediate Similarity	NPC108581
0.807	Intermediate Similarity	NPC478205
0.807	Intermediate Similarity	NPC478206
0.8058	Intermediate Similarity	NPC183012
0.8056	Intermediate Similarity	NPC477125
0.8056	Intermediate Similarity	NPC252296
0.8056	Intermediate Similarity	NPC218158
0.8053	Intermediate Similarity	NPC196931
0.8053	Intermediate Similarity	NPC471816
0.8039	Intermediate Similarity	NPC205034
0.8039	Intermediate Similarity	NPC162615
0.8039	Intermediate Similarity	NPC152778
0.8037	Intermediate Similarity	NPC476237
0.8037	Intermediate Similarity	NPC476848
0.8037	Intermediate Similarity	NPC176883
0.8037	Intermediate Similarity	NPC72151
0.8037	Intermediate Similarity	NPC254202
0.8036	Intermediate Similarity	NPC475966
0.8036	Intermediate Similarity	NPC477126
0.8036	Intermediate Similarity	NPC469454
0.8036	Intermediate Similarity	NPC469463
0.8036	Intermediate Similarity	NPC25909
0.8036	Intermediate Similarity	NPC469496
0.8034	Intermediate Similarity	NPC55602
0.802	Intermediate Similarity	NPC475776
0.802	Intermediate Similarity	NPC232202
0.802	Intermediate Similarity	NPC78973
0.8019	Intermediate Similarity	NPC222875
0.8019	Intermediate Similarity	NPC295110
0.8019	Intermediate Similarity	NPC268829
0.8019	Intermediate Similarity	NPC235142
0.8019	Intermediate Similarity	NPC247701
0.8019	Intermediate Similarity	NPC115899
0.8019	Intermediate Similarity	NPC11974
0.8019	Intermediate Similarity	NPC472554
0.8019	Intermediate Similarity	NPC168319
0.8019	Intermediate Similarity	NPC194028
0.8019	Intermediate Similarity	NPC303559
0.8019	Intermediate Similarity	NPC25177
0.8018	Intermediate Similarity	NPC304180
0.8018	Intermediate Similarity	NPC179798
0.8	Intermediate Similarity	NPC228477
0.8	Intermediate Similarity	NPC312536
0.8	Intermediate Similarity	NPC119036
0.8	Intermediate Similarity	NPC107806
0.8	Intermediate Similarity	NPC226863
0.8	Intermediate Similarity	NPC472302
0.8	Intermediate Similarity	NPC474243
0.8	Intermediate Similarity	NPC206618
0.8	Intermediate Similarity	NPC137911
0.8	Intermediate Similarity	NPC469380
0.8	Intermediate Similarity	NPC475065
0.8	Intermediate Similarity	NPC72647
0.7982	Intermediate Similarity	NPC180744
0.7982	Intermediate Similarity	NPC98249
0.7982	Intermediate Similarity	NPC143609
0.7982	Intermediate Similarity	NPC329048
0.7982	Intermediate Similarity	NPC473656
0.7982	Intermediate Similarity	NPC330011
0.7982	Intermediate Similarity	NPC131665
0.7982	Intermediate Similarity	NPC184512
0.7982	Intermediate Similarity	NPC216636
0.7982	Intermediate Similarity	NPC53396
0.7982	Intermediate Similarity	NPC255387
0.7981	Intermediate Similarity	NPC209297
0.7981	Intermediate Similarity	NPC475380
0.7981	Intermediate Similarity	NPC284518
0.798	Intermediate Similarity	NPC131813
0.7963	Intermediate Similarity	NPC146731
0.7961	Intermediate Similarity	NPC250075
0.7961	Intermediate Similarity	NPC24861
0.7961	Intermediate Similarity	NPC140277
0.7961	Intermediate Similarity	NPC477129
0.7961	Intermediate Similarity	NPC477130

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 NPC302788 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	159
0.1-0.2	1192
0.2-0.3	3367
0.3-0.4	2726
0.4-0.5	1118
0.5-0.6	297
0.6-0.7	213
0.7-0.8	75
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
0.8173	Intermediate Similarity	NPD7638	Approved
0.8095	Intermediate Similarity	NPD7640	Approved
0.8095	Intermediate Similarity	NPD7639	Approved
0.7928	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7838	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7664	Intermediate Similarity	NPD4225	Approved
0.7658	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.7589	Intermediate Similarity	NPD6686	Approved
0.7576	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7459	Intermediate Similarity	NPD7507	Approved
0.7455	Intermediate Similarity	NPD7632	Discontinued
0.7453	Intermediate Similarity	NPD7748	Approved
0.7419	Intermediate Similarity	NPD7319	Approved
0.7411	Intermediate Similarity	NPD6008	Approved
0.7407	Intermediate Similarity	NPD7902	Approved
0.7373	Intermediate Similarity	NPD7115	Discovery
0.7353	Intermediate Similarity	NPD1694	Approved
0.7328	Intermediate Similarity	NPD6053	Discontinued
0.7311	Intermediate Similarity	NPD7327	Approved
0.7311	Intermediate Similarity	NPD7328	Approved
0.7281	Intermediate Similarity	NPD7320	Approved
0.7264	Intermediate Similarity	NPD7515	Phase 2
0.7257	Intermediate Similarity	NPD5739	Approved
0.7257	Intermediate Similarity	NPD7128	Approved
0.7257	Intermediate Similarity	NPD6675	Approved
0.7257	Intermediate Similarity	NPD6402	Approved
0.725	Intermediate Similarity	NPD7516	Approved
0.7222	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7217	Intermediate Similarity	NPD6372	Approved
0.7217	Intermediate Similarity	NPD6373	Approved
0.7196	Intermediate Similarity	NPD6399	Phase 3
0.7131	Intermediate Similarity	NPD8379	Approved
0.7131	Intermediate Similarity	NPD8296	Approved
0.7131	Intermediate Similarity	NPD8335	Approved
0.7131	Intermediate Similarity	NPD8378	Approved
0.7131	Intermediate Similarity	NPD7503	Approved
0.7131	Intermediate Similarity	NPD8380	Approved
0.713	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.713	Intermediate Similarity	NPD5282	Discontinued
0.713	Intermediate Similarity	NPD6881	Approved
0.713	Intermediate Similarity	NPD7900	Approved
0.713	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.713	Intermediate Similarity	NPD6899	Approved
0.7117	Intermediate Similarity	NPD6648	Approved
0.7115	Intermediate Similarity	NPD3618	Phase 1
0.7103	Intermediate Similarity	NPD7637	Suspended
0.7094	Intermediate Similarity	NPD6650	Approved
0.7094	Intermediate Similarity	NPD6649	Approved
0.7091	Intermediate Similarity	NPD6084	Phase 2
0.7091	Intermediate Similarity	NPD6083	Phase 2
0.7049	Intermediate Similarity	NPD8377	Approved
0.7049	Intermediate Similarity	NPD8294	Approved
0.7043	Intermediate Similarity	NPD5701	Approved
0.7043	Intermediate Similarity	NPD5697	Approved
0.7037	Intermediate Similarity	NPD5779	Approved
0.7037	Intermediate Similarity	NPD5778	Approved
0.7027	Intermediate Similarity	NPD5696	Approved
0.7009	Intermediate Similarity	NPD6883	Approved
0.7009	Intermediate Similarity	NPD7102	Approved
0.7009	Intermediate Similarity	NPD7290	Approved
0.6992	Remote Similarity	NPD8033	Approved
0.6981	Remote Similarity	NPD6903	Approved
0.696	Remote Similarity	NPD7492	Approved
0.6952	Remote Similarity	NPD6409	Approved
0.6952	Remote Similarity	NPD7146	Approved
0.6952	Remote Similarity	NPD7521	Approved
0.6952	Remote Similarity	NPD6684	Approved
0.6952	Remote Similarity	NPD5330	Approved
0.6952	Remote Similarity	NPD7334	Approved
0.6949	Remote Similarity	NPD6869	Approved
0.6949	Remote Similarity	NPD6847	Approved
0.6949	Remote Similarity	NPD8130	Phase 1
0.6949	Remote Similarity	NPD6617	Approved
0.6944	Remote Similarity	NPD8035	Phase 2
0.6944	Remote Similarity	NPD8034	Phase 2
0.6923	Remote Similarity	NPD6014	Approved
0.6923	Remote Similarity	NPD6012	Approved
0.6923	Remote Similarity	NPD6013	Approved
0.6916	Remote Similarity	NPD5328	Approved
0.6911	Remote Similarity	NPD6054	Approved
0.6911	Remote Similarity	NPD6059	Approved
0.6909	Remote Similarity	NPD5695	Phase 3
0.6905	Remote Similarity	NPD6616	Approved
0.6903	Remote Similarity	NPD5344	Discontinued
0.6897	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6891	Remote Similarity	NPD8297	Approved
0.6891	Remote Similarity	NPD6882	Approved
0.6852	Remote Similarity	NPD5207	Approved
0.6852	Remote Similarity	NPD6698	Approved
0.6852	Remote Similarity	NPD46	Approved
0.685	Remote Similarity	NPD7078	Approved
0.685	Remote Similarity	NPD8293	Discontinued
0.6838	Remote Similarity	NPD6011	Approved
0.6833	Remote Similarity	NPD4632	Approved
0.6827	Remote Similarity	NPD6695	Phase 3
0.6822	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6822	Remote Similarity	NPD5737	Approved
0.6822	Remote Similarity	NPD6672	Approved
0.6818	Remote Similarity	NPD6001	Approved
0.6807	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.68	Remote Similarity	NPD6370	Approved
0.6797	Remote Similarity	NPD7736	Approved
0.6789	Remote Similarity	NPD5284	Approved
0.6789	Remote Similarity	NPD6411	Approved
0.6789	Remote Similarity	NPD6079	Approved
0.6789	Remote Similarity	NPD5281	Approved
0.6789	Remote Similarity	NPD5693	Phase 1
0.6786	Remote Similarity	NPD4755	Approved
0.6774	Remote Similarity	NPD6319	Approved
0.6762	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6759	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6752	Remote Similarity	NPD6412	Phase 2
0.6729	Remote Similarity	NPD3573	Approved
0.6727	Remote Similarity	NPD4202	Approved
0.6723	Remote Similarity	NPD6371	Approved
0.672	Remote Similarity	NPD8516	Approved
0.672	Remote Similarity	NPD6016	Approved
0.672	Remote Similarity	NPD6015	Approved
0.672	Remote Similarity	NPD8513	Phase 3
0.672	Remote Similarity	NPD8515	Approved
0.672	Remote Similarity	NPD8517	Approved
0.6698	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6696	Remote Similarity	NPD4697	Phase 3
0.6696	Remote Similarity	NPD5211	Phase 2
0.6694	Remote Similarity	NPD8133	Approved
0.6667	Remote Similarity	NPD6009	Approved
0.6667	Remote Similarity	NPD4696	Approved
0.6667	Remote Similarity	NPD5988	Approved
0.6667	Remote Similarity	NPD4700	Approved
0.6667	Remote Similarity	NPD5286	Approved
0.6667	Remote Similarity	NPD5285	Approved
0.6641	Remote Similarity	NPD7260	Phase 2
0.6639	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6636	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6636	Remote Similarity	NPD6050	Approved
0.6614	Remote Similarity	NPD7604	Phase 2
0.6614	Remote Similarity	NPD8328	Phase 3
0.6606	Remote Similarity	NPD4753	Phase 2
0.6606	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6606	Remote Similarity	NPD6101	Approved
0.6606	Remote Similarity	NPD6904	Approved
0.6606	Remote Similarity	NPD6673	Approved
0.6606	Remote Similarity	NPD1695	Approved
0.6606	Remote Similarity	NPD6080	Approved
0.6606	Remote Similarity	NPD6051	Approved
0.6604	Remote Similarity	NPD3665	Phase 1
0.6604	Remote Similarity	NPD4786	Approved
0.6604	Remote Similarity	NPD3133	Approved
0.6604	Remote Similarity	NPD3666	Approved
0.6591	Remote Similarity	NPD6845	Suspended
0.6587	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6587	Remote Similarity	NPD5983	Phase 2
0.6585	Remote Similarity	NPD6274	Approved
0.6581	Remote Similarity	NPD5141	Approved
0.6579	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6574	Remote Similarity	NPD4250	Approved
0.6574	Remote Similarity	NPD7750	Discontinued
0.6574	Remote Similarity	NPD7524	Approved
0.6574	Remote Similarity	NPD4251	Approved
0.6571	Remote Similarity	NPD3667	Approved
0.656	Remote Similarity	NPD7100	Approved
0.656	Remote Similarity	NPD7101	Approved
0.6552	Remote Similarity	NPD4633	Approved
0.6552	Remote Similarity	NPD5224	Approved
0.6552	Remote Similarity	NPD5225	Approved
0.6552	Remote Similarity	NPD5226	Approved
0.6549	Remote Similarity	NPD5222	Approved
0.6549	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6549	Remote Similarity	NPD5221	Approved
0.6545	Remote Similarity	NPD7838	Discovery
0.6545	Remote Similarity	NPD5692	Phase 3
0.6545	Remote Similarity	NPD5785	Approved
0.6538	Remote Similarity	NPD6930	Phase 2
0.6538	Remote Similarity	NPD6931	Approved
0.6535	Remote Similarity	NPD8039	Approved
0.6512	Remote Similarity	NPD6336	Discontinued
0.6509	Remote Similarity	NPD7154	Phase 3
0.6496	Remote Similarity	NPD5175	Approved
0.6496	Remote Similarity	NPD5174	Approved
0.6491	Remote Similarity	NPD5173	Approved
0.6486	Remote Similarity	NPD5694	Approved
0.6484	Remote Similarity	NPD6067	Discontinued
0.6481	Remote Similarity	NPD4519	Discontinued
0.6481	Remote Similarity	NPD4249	Approved
0.6481	Remote Similarity	NPD5279	Phase 3
0.6481	Remote Similarity	NPD4623	Approved
0.648	Remote Similarity	NPD6335	Approved
0.6466	Remote Similarity	NPD5223	Approved
0.6462	Remote Similarity	NPD8074	Phase 3
0.646	Remote Similarity	NPD5210	Approved
0.646	Remote Similarity	NPD4629	Approved
0.6457	Remote Similarity	NPD6908	Approved
0.6457	Remote Similarity	NPD6921	Approved
0.6457	Remote Similarity	NPD6909	Approved
0.6452	Remote Similarity	NPD6868	Approved
0.6449	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6446	Remote Similarity	NPD4634	Approved
0.6442	Remote Similarity	NPD6929	Approved
0.6415	Remote Similarity	NPD4223	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