NPASS Compound

Structure

NPC472687 OpenBabel07101719132D 41 43 0 0 1 0 0 0 0 0999 V2000 -3.1007 1.1495 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2073 -0.5402 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9609 -2.1752 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8267 -4.8552 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8267 -4.8552 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8267 -4.2958 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4802 -4.2958 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8822 -0.3204 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9039 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0771 0.4773 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7802 -0.8597 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1596 1.3096 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0730 -1.8906 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6682 -1.1443 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -3.4233 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6535 -2.8639 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8267 -2.9460 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8267 -2.3866 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1850 -1.6061 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4897 -0.7174 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5614 0.2950 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6121 -1.2865 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -4.3779 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6535 -3.8185 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5504 0.5747 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 0.8267 -1.0367 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8267 -1.4319 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1225 -0.4773 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.6093 0.7349 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.9546 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6535 -0.9546 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8267 0.4773 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0771 -0.4773 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1637 -0.7174 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6535 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.2775 1.6300 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8267 -1.4319 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8267 1.4319 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.5544 -1.3041 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5614 -1.2496 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 12 1 0 0 0 0 2 22 1 0 0 0 0 3 22 1 0 0 0 0 4 23 1 0 0 0 0 5 23 1 0 0 0 0 6 24 1 0 0 0 0 7 24 1 0 0 0 0 8 25 1 0 0 0 0 9 33 1 0 0 0 0 10 33 1 0 0 0 0 11 34 1 0 0 0 0 12 25 1 0 0 0 0 13 14 1 0 0 0 0 13 19 1 0 0 0 0 14 22 2 0 0 0 0 15 17 1 0 0 0 0 15 23 2 0 0 0 0 16 18 1 0 0 0 0 16 24 2 0 0 0 0 17 26 1 0 0 0 0 18 27 1 0 0 0 0 19 34 1 0 0 0 0 20 26 1 0 0 0 0 21 28 1 0 0 0 0 21 35 1 0 0 0 0 25 29 1 0 0 0 0 26 34 1 6 0 0 0 27 30 1 0 0 0 0 27 31 2 0 0 0 0 28 33 1 1 0 0 0 28 41 1 0 0 0 0 29 37 2 0 0 0 0 30 36 1 0 0 0 0 30 38 2 0 0 0 0 31 35 1 0 0 0 0 31 41 1 0 0 0 0 32 35 1 0 0 0 0 32 36 1 0 0 0 0 32 39 2 0 0 0 0 33 40 1 0 0 0 0 34 36 1 1 0 0 0 35 20 1 6 0 0 0 36 29 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	566.4
Volume:	631.038
LogP:	8.255
LogD:	5.91
LogS:	-5.487
# Rotatable Bonds:	11
TPSA:	80.67
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.202
Synthetic Accessibility Score:	6.51
Fsp3:	0.694
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.926
MDCK Permeability:	1.5200273082882632e-05
Pgp-inhibitor:	0.017
Pgp-substrate:	0.976
Human Intestinal Absorption (HIA):	0.036
20% Bioavailability (F20%):	0.921
30% Bioavailability (F30%):	0.974

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.942
Plasma Protein Binding (PPB):	83.29016876220703%
Volume Distribution (VD):	2.736
Pgp-substrate:	6.019835948944092%

ADMET: Metabolism

CYP1A2-inhibitor:	0.014
CYP1A2-substrate:	0.127
CYP2C19-inhibitor:	0.236
CYP2C19-substrate:	0.842
CYP2C9-inhibitor:	0.374
CYP2C9-substrate:	0.078
CYP2D6-inhibitor:	0.384
CYP2D6-substrate:	0.01
CYP3A4-inhibitor:	0.888
CYP3A4-substrate:	0.885

ADMET: Excretion

Clearance (CL):	14.326
Half-life (T1/2):	0.024

ADMET: Toxicity

hERG Blockers:	0.002
Human Hepatotoxicity (H-HT):	0.947
Drug-inuced Liver Injury (DILI):	0.743
AMES Toxicity:	0.021
Rat Oral Acute Toxicity:	0.807
Maximum Recommended Daily Dose:	0.506
Skin Sensitization:	0.332
Carcinogencity:	0.6
Eye Corrosion:	0.006
Eye Irritation:	0.026
Respiratory Toxicity:	0.987

Download Data

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

Natural Product: NPC472687

Natural Product ID:	NPC472687
*Common Name:**	FBBDPYYKVMTRAB-IKJVFAJVSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	FBBDPYYKVMTRAB-IKJVFAJVSA-N
Standard InCHI:	InChI=1S/C36H54O5/c1-12-25(8)29(37)36-30(38)27(18-16-24(6)7)31-35(32(36)39,21-28(41-31)33(9,10)40)20-26(17-15-23(4)5)34(36,11)19-13-14-22(2)3/h14-16,25-26,28,40H,12-13,17-21H2,1-11H3/t25?,26-,28-,34+,35-,36-/m0/s1
SMILES:	CCC(C(=O)[C@]12C(=O)C(=C3[C@@](C1=O)(C[C@H](O3)C(O)(C)C)C[C@@H]([C@@]2(C)CCC=C(C)C)CC=C(C)C)CC=C(C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3581589
PubChem CID:	16094885
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001549] Monoterpenoids

*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
NPO19915	Hypericum henryi	Species	Hypericaceae	Eukaryota	aerial parts	Yunnan, China	n.a.	PMID[25871261]
NPO19915	Hypericum henryi	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19915	Hypericum henryi	Species	Hypericaceae	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	5

Activity Type	# Activity
Cell Line	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT116	Cell Line	HL-60	Homo sapiens	IC50	>	40000.0	nM	PMID[496107]
NPT659	Cell Line	SMMC-7721	Homo sapiens	IC50	>	40000.0	nM	PMID[496107]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	40000.0	nM	PMID[496107]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	>	40000.0	nM	PMID[496107]
NPT660	Cell Line	SW480	Homo sapiens	IC50	>	40000.0	nM	PMID[496107]

☑ 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 NPC472687 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	181
0.1-0.2	1153
0.2-0.3	4574
0.3-0.4	8851
0.4-0.5	13046
0.5-0.6	7105
0.6-0.7	6509
0.7-0.8	1214
0.8-0.85	18
0.85-0.9	24
0.9-0.95	11
0.95-1	11

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC203388
1.0	High Similarity	NPC99657
1.0	High Similarity	NPC471331
1.0	High Similarity	NPC471330
0.989	High Similarity	NPC27105
0.9462	High Similarity	NPC472731
0.9462	High Similarity	NPC472732
0.9381	High Similarity	NPC471332
0.9381	High Similarity	NPC471333
0.9355	High Similarity	NPC472734
0.9355	High Similarity	NPC472733
0.9263	High Similarity	NPC472727
0.9263	High Similarity	NPC472728
0.9158	High Similarity	NPC177680
0.9158	High Similarity	NPC472730
0.9158	High Similarity	NPC472729
0.9158	High Similarity	NPC153776
0.914	High Similarity	NPC114162
0.914	High Similarity	NPC469819
0.8947	High Similarity	NPC472675
0.8947	High Similarity	NPC21681
0.8901	High Similarity	NPC38885
0.875	High Similarity	NPC135576
0.875	High Similarity	NPC93271
0.8318	Intermediate Similarity	NPC247069
0.8283	Intermediate Similarity	NPC239895
0.8242	Intermediate Similarity	NPC472684
0.8242	Intermediate Similarity	NPC44963
0.819	Intermediate Similarity	NPC470257
0.8155	Intermediate Similarity	NPC255309
0.8119	Intermediate Similarity	NPC54705
0.8077	Intermediate Similarity	NPC96377
0.8039	Intermediate Similarity	NPC101067
0.8039	Intermediate Similarity	NPC476134
0.8037	Intermediate Similarity	NPC324683
0.8	Intermediate Similarity	NPC58370
0.8	Intermediate Similarity	NPC8803
0.8	Intermediate Similarity	NPC43285
0.7981	Intermediate Similarity	NPC13385
0.798	Intermediate Similarity	NPC477241
0.7961	Intermediate Similarity	NPC473163
0.7935	Intermediate Similarity	NPC472948
0.7925	Intermediate Similarity	NPC473288
0.7921	Intermediate Similarity	NPC477268
0.7921	Intermediate Similarity	NPC472689
0.7921	Intermediate Similarity	NPC472690
0.7921	Intermediate Similarity	NPC477267
0.7905	Intermediate Similarity	NPC102352
0.7885	Intermediate Similarity	NPC475321
0.787	Intermediate Similarity	NPC474229
0.7864	Intermediate Similarity	NPC477871
0.7864	Intermediate Similarity	NPC476213
0.7864	Intermediate Similarity	NPC477870
0.7864	Intermediate Similarity	NPC181645
0.7864	Intermediate Similarity	NPC476246
0.7849	Intermediate Similarity	NPC189237
0.7835	Intermediate Similarity	NPC476706
0.7835	Intermediate Similarity	NPC476708
0.7835	Intermediate Similarity	NPC476707
0.783	Intermediate Similarity	NPC144854
0.783	Intermediate Similarity	NPC3316
0.781	Intermediate Similarity	NPC146731
0.781	Intermediate Similarity	NPC471293
0.78	Intermediate Similarity	NPC473172
0.78	Intermediate Similarity	NPC196227
0.7798	Intermediate Similarity	NPC269530
0.7798	Intermediate Similarity	NPC207251
0.7788	Intermediate Similarity	NPC476126
0.7788	Intermediate Similarity	NPC476235
0.7788	Intermediate Similarity	NPC478051
0.7778	Intermediate Similarity	NPC116726
0.7778	Intermediate Similarity	NPC474567
0.7778	Intermediate Similarity	NPC5284
0.7767	Intermediate Similarity	NPC167974
0.7767	Intermediate Similarity	NPC46761
0.7767	Intermediate Similarity	NPC474720
0.7757	Intermediate Similarity	NPC277017
0.7757	Intermediate Similarity	NPC154608
0.7757	Intermediate Similarity	NPC192813
0.7748	Intermediate Similarity	NPC207217
0.7745	Intermediate Similarity	NPC124246
0.7745	Intermediate Similarity	NPC273269
0.7739	Intermediate Similarity	NPC141196
0.7739	Intermediate Similarity	NPC238005
0.7739	Intermediate Similarity	NPC1980
0.7736	Intermediate Similarity	NPC292588
0.7732	Intermediate Similarity	NPC251808
0.7732	Intermediate Similarity	NPC474174
0.7727	Intermediate Similarity	NPC326264
0.7727	Intermediate Similarity	NPC198539
0.7723	Intermediate Similarity	NPC473170
0.7717	Intermediate Similarity	NPC478247
0.7717	Intermediate Similarity	NPC478246
0.7714	Intermediate Similarity	NPC474207
0.7714	Intermediate Similarity	NPC117185
0.7714	Intermediate Similarity	NPC474330
0.77	Intermediate Similarity	NPC61275
0.77	Intermediate Similarity	NPC474807
0.7692	Intermediate Similarity	NPC475867
0.7692	Intermediate Similarity	NPC270155
0.7692	Intermediate Similarity	NPC471401
0.7692	Intermediate Similarity	NPC9878
0.7685	Intermediate Similarity	NPC87335
0.7685	Intermediate Similarity	NPC304495
0.7685	Intermediate Similarity	NPC153239
0.7685	Intermediate Similarity	NPC310546
0.7679	Intermediate Similarity	NPC287343
0.7679	Intermediate Similarity	NPC470854
0.7679	Intermediate Similarity	NPC97908
0.7679	Intermediate Similarity	NPC122033
0.7679	Intermediate Similarity	NPC474654
0.7677	Intermediate Similarity	NPC472325
0.7664	Intermediate Similarity	NPC220974
0.766	Intermediate Similarity	NPC327002
0.7658	Intermediate Similarity	NPC326542
0.7653	Intermediate Similarity	NPC143025
0.7653	Intermediate Similarity	NPC228415
0.7653	Intermediate Similarity	NPC269677
0.7653	Intermediate Similarity	NPC87189
0.7647	Intermediate Similarity	NPC146239
0.7647	Intermediate Similarity	NPC91439
0.7647	Intermediate Similarity	NPC473164
0.7642	Intermediate Similarity	NPC470104
0.7642	Intermediate Similarity	NPC40170
0.7642	Intermediate Similarity	NPC209502
0.7642	Intermediate Similarity	NPC204833
0.7642	Intermediate Similarity	NPC296950
0.7636	Intermediate Similarity	NPC205534
0.7629	Intermediate Similarity	NPC470345
0.7629	Intermediate Similarity	NPC477479
0.7629	Intermediate Similarity	NPC477478
0.7624	Intermediate Similarity	NPC67831
0.7624	Intermediate Similarity	NPC174051
0.7624	Intermediate Similarity	NPC103527
0.7624	Intermediate Similarity	NPC258674
0.7619	Intermediate Similarity	NPC163249
0.7619	Intermediate Similarity	NPC473928
0.7619	Intermediate Similarity	NPC478176
0.7615	Intermediate Similarity	NPC473627
0.7615	Intermediate Similarity	NPC239097
0.7615	Intermediate Similarity	NPC210005
0.7615	Intermediate Similarity	NPC76084
0.7615	Intermediate Similarity	NPC5103
0.7611	Intermediate Similarity	NPC297179
0.7611	Intermediate Similarity	NPC106644
0.7611	Intermediate Similarity	NPC17772
0.7609	Intermediate Similarity	NPC325946
0.7607	Intermediate Similarity	NPC198714
0.76	Intermediate Similarity	NPC146852
0.76	Intermediate Similarity	NPC476705
0.76	Intermediate Similarity	NPC471329
0.76	Intermediate Similarity	NPC262870
0.76	Intermediate Similarity	NPC296114
0.76	Intermediate Similarity	NPC19114
0.7593	Intermediate Similarity	NPC151393
0.7593	Intermediate Similarity	NPC19412
0.7589	Intermediate Similarity	NPC96312
0.7589	Intermediate Similarity	NPC16081
0.7589	Intermediate Similarity	NPC173686
0.7589	Intermediate Similarity	NPC328374
0.7589	Intermediate Similarity	NPC40632
0.7589	Intermediate Similarity	NPC251236
0.7586	Intermediate Similarity	NPC18945
0.7586	Intermediate Similarity	NPC265557
0.7586	Intermediate Similarity	NPC91693
0.7586	Intermediate Similarity	NPC105926
0.7579	Intermediate Similarity	NPC212083
0.7576	Intermediate Similarity	NPC269267
0.7576	Intermediate Similarity	NPC186688
0.7576	Intermediate Similarity	NPC474570
0.7576	Intermediate Similarity	NPC477943
0.7573	Intermediate Similarity	NPC272451
0.7573	Intermediate Similarity	NPC473161
0.7573	Intermediate Similarity	NPC473574
0.7573	Intermediate Similarity	NPC20078
0.757	Intermediate Similarity	NPC95243
0.757	Intermediate Similarity	NPC85829
0.757	Intermediate Similarity	NPC296945
0.757	Intermediate Similarity	NPC476027
0.757	Intermediate Similarity	NPC149047
0.757	Intermediate Similarity	NPC260268
0.757	Intermediate Similarity	NPC49958
0.757	Intermediate Similarity	NPC214264
0.757	Intermediate Similarity	NPC319077
0.757	Intermediate Similarity	NPC202167
0.757	Intermediate Similarity	NPC171137
0.757	Intermediate Similarity	NPC48733
0.757	Intermediate Similarity	NPC152695
0.757	Intermediate Similarity	NPC150531
0.757	Intermediate Similarity	NPC302607
0.757	Intermediate Similarity	NPC478052
0.757	Intermediate Similarity	NPC50692
0.757	Intermediate Similarity	NPC97202
0.757	Intermediate Similarity	NPC63023
0.7568	Intermediate Similarity	NPC469454
0.7568	Intermediate Similarity	NPC250109
0.7568	Intermediate Similarity	NPC317210
0.7568	Intermediate Similarity	NPC52634
0.7568	Intermediate Similarity	NPC469496
0.7568	Intermediate Similarity	NPC469463

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 NPC472687 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	154
0.1-0.2	1540
0.2-0.3	3986
0.3-0.4	2300
0.4-0.5	702
0.5-0.6	214
0.6-0.7	199
0.7-0.8	55
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
0.7624	Intermediate Similarity	NPD5282	Discontinued
0.74	Intermediate Similarity	NPD5328	Approved
0.7339	Intermediate Similarity	NPD6412	Phase 2
0.7328	Intermediate Similarity	NPD6054	Approved
0.7328	Intermediate Similarity	NPD6059	Approved
0.7297	Intermediate Similarity	NPD4634	Approved
0.7282	Intermediate Similarity	NPD7748	Approved
0.7273	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD3618	Phase 1
0.7255	Intermediate Similarity	NPD6079	Approved
0.7245	Intermediate Similarity	NPD3133	Approved
0.7245	Intermediate Similarity	NPD3665	Phase 1
0.7245	Intermediate Similarity	NPD3666	Approved
0.7238	Intermediate Similarity	NPD7902	Approved
0.7203	Intermediate Similarity	NPD6370	Approved
0.7184	Intermediate Similarity	NPD6399	Phase 3
0.7179	Intermediate Similarity	NPD6319	Approved
0.7168	Intermediate Similarity	NPD8297	Approved
0.7143	Intermediate Similarity	NPD4697	Phase 3
0.7143	Intermediate Similarity	NPD8328	Phase 3
0.7119	Intermediate Similarity	NPD6015	Approved
0.7119	Intermediate Similarity	NPD6016	Approved
0.7107	Intermediate Similarity	NPD8293	Discontinued
0.7105	Intermediate Similarity	NPD4632	Approved
0.71	Intermediate Similarity	NPD6684	Approved
0.71	Intermediate Similarity	NPD7334	Approved
0.71	Intermediate Similarity	NPD7146	Approved
0.71	Intermediate Similarity	NPD7521	Approved
0.71	Intermediate Similarity	NPD6409	Approved
0.71	Intermediate Similarity	NPD5330	Approved
0.7091	Intermediate Similarity	NPD6675	Approved
0.7091	Intermediate Similarity	NPD6402	Approved
0.7091	Intermediate Similarity	NPD6008	Approved
0.7091	Intermediate Similarity	NPD5739	Approved
0.7091	Intermediate Similarity	NPD7128	Approved
0.7083	Intermediate Similarity	NPD7492	Approved
0.7075	Intermediate Similarity	NPD6084	Phase 2
0.7075	Intermediate Similarity	NPD6083	Phase 2
0.7075	Intermediate Similarity	NPD4755	Approved
0.7071	Intermediate Similarity	NPD4786	Approved
0.7069	Intermediate Similarity	NPD7115	Discovery
0.7059	Intermediate Similarity	NPD5988	Approved
0.7059	Intermediate Similarity	NPD4753	Phase 2
0.7054	Intermediate Similarity	NPD6373	Approved
0.7054	Intermediate Similarity	NPD6372	Approved
0.7049	Intermediate Similarity	NPD7736	Approved
0.7048	Intermediate Similarity	NPD5695	Phase 3
0.7041	Intermediate Similarity	NPD4223	Phase 3
0.7041	Intermediate Similarity	NPD3667	Approved
0.7041	Intermediate Similarity	NPD4221	Approved
0.7025	Intermediate Similarity	NPD6616	Approved
0.701	Intermediate Similarity	NPD4695	Discontinued
0.7009	Intermediate Similarity	NPD4225	Approved
0.7009	Intermediate Similarity	NPD5696	Approved
0.7	Intermediate Similarity	NPD5329	Approved
0.6981	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD5221	Approved
0.6981	Remote Similarity	NPD5222	Approved
0.6967	Remote Similarity	NPD7078	Approved
0.6964	Remote Similarity	NPD7320	Approved
0.6964	Remote Similarity	NPD6899	Approved
0.6964	Remote Similarity	NPD6881	Approved
0.6961	Remote Similarity	NPD6903	Approved
0.6961	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6961	Remote Similarity	NPD6672	Approved
0.6961	Remote Similarity	NPD5737	Approved
0.6952	Remote Similarity	NPD7900	Approved
0.6952	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD4700	Approved
0.6944	Remote Similarity	NPD4696	Approved
0.6944	Remote Similarity	NPD5285	Approved
0.6944	Remote Similarity	NPD5286	Approved
0.6931	Remote Similarity	NPD5279	Phase 3
0.693	Remote Similarity	NPD8130	Phase 1
0.693	Remote Similarity	NPD6650	Approved
0.693	Remote Similarity	NPD6649	Approved
0.6923	Remote Similarity	NPD6411	Approved
0.6923	Remote Similarity	NPD7515	Phase 2
0.6916	Remote Similarity	NPD5173	Approved
0.6911	Remote Similarity	NPD6033	Approved
0.69	Remote Similarity	NPD4197	Approved
0.6887	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD4629	Approved
0.6887	Remote Similarity	NPD5210	Approved
0.6881	Remote Similarity	NPD5223	Approved
0.6875	Remote Similarity	NPD5701	Approved
0.6875	Remote Similarity	NPD5697	Approved
0.6869	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD5778	Approved
0.6857	Remote Similarity	NPD5779	Approved
0.6857	Remote Similarity	NPD4202	Approved
0.6842	Remote Similarity	NPD7290	Approved
0.6842	Remote Similarity	NPD7102	Approved
0.6842	Remote Similarity	NPD6883	Approved
0.6818	Remote Similarity	NPD5211	Phase 2
0.6818	Remote Similarity	NPD5224	Approved
0.6818	Remote Similarity	NPD5225	Approved
0.6818	Remote Similarity	NPD5226	Approved
0.6818	Remote Similarity	NPD4633	Approved
0.6814	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6814	Remote Similarity	NPD6011	Approved
0.6814	Remote Similarity	NPD6686	Approved
0.6804	Remote Similarity	NPD3617	Approved
0.68	Remote Similarity	NPD6110	Phase 1
0.6783	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6783	Remote Similarity	NPD6847	Approved
0.6783	Remote Similarity	NPD6869	Approved
0.6783	Remote Similarity	NPD6617	Approved
0.678	Remote Similarity	NPD6009	Approved
0.6765	Remote Similarity	NPD5280	Approved
0.6765	Remote Similarity	NPD4623	Approved
0.6765	Remote Similarity	NPD4690	Approved
0.6765	Remote Similarity	NPD4694	Approved
0.6765	Remote Similarity	NPD4519	Discontinued
0.6765	Remote Similarity	NPD4689	Approved
0.6765	Remote Similarity	NPD5205	Approved
0.6765	Remote Similarity	NPD4693	Phase 3
0.6765	Remote Similarity	NPD4138	Approved
0.6765	Remote Similarity	NPD5690	Phase 2
0.6765	Remote Similarity	NPD4688	Approved
0.6762	Remote Similarity	NPD5284	Approved
0.6762	Remote Similarity	NPD5281	Approved
0.6757	Remote Similarity	NPD4754	Approved
0.6757	Remote Similarity	NPD5174	Approved
0.6757	Remote Similarity	NPD5175	Approved
0.6754	Remote Similarity	NPD6014	Approved
0.6754	Remote Similarity	NPD6012	Approved
0.6754	Remote Similarity	NPD6013	Approved
0.6733	Remote Similarity	NPD3668	Phase 3
0.6731	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6731	Remote Similarity	NPD6904	Approved
0.6731	Remote Similarity	NPD6101	Approved
0.6731	Remote Similarity	NPD6673	Approved
0.6731	Remote Similarity	NPD6080	Approved
0.6729	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6726	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6724	Remote Similarity	NPD6053	Discontinued
0.6724	Remote Similarity	NPD6882	Approved
0.6721	Remote Similarity	NPD7604	Phase 2
0.6703	Remote Similarity	NPD7331	Phase 2
0.6699	Remote Similarity	NPD3573	Approved
0.6697	Remote Similarity	NPD7638	Approved
0.6696	Remote Similarity	NPD5141	Approved
0.6696	Remote Similarity	NPD6371	Approved
0.6694	Remote Similarity	NPD5983	Phase 2
0.6667	Remote Similarity	NPD5207	Approved
0.6667	Remote Similarity	NPD1694	Approved
0.6639	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6637	Remote Similarity	NPD4767	Approved
0.6637	Remote Similarity	NPD4768	Approved
0.6636	Remote Similarity	NPD7640	Approved
0.6636	Remote Similarity	NPD7639	Approved
0.6634	Remote Similarity	NPD4788	Approved
0.6613	Remote Similarity	NPD6336	Discontinued
0.6609	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6609	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6604	Remote Similarity	NPD6050	Approved
0.6604	Remote Similarity	NPD7983	Approved
0.6593	Remote Similarity	NPD7341	Phase 2
0.6587	Remote Similarity	NPD7319	Approved
0.6571	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6538	Remote Similarity	NPD7524	Approved
0.6535	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6529	Remote Similarity	NPD4522	Approved
0.6522	Remote Similarity	NPD4730	Approved
0.6522	Remote Similarity	NPD5128	Approved
0.6522	Remote Similarity	NPD4729	Approved
0.6509	Remote Similarity	NPD5692	Phase 3
0.6481	Remote Similarity	NPD6001	Approved
0.648	Remote Similarity	NPD7507	Approved
0.6476	Remote Similarity	NPD5208	Approved
0.6452	Remote Similarity	NPD6067	Discontinued
0.6449	Remote Similarity	NPD5693	Phase 1
0.6449	Remote Similarity	NPD8035	Phase 2
0.6449	Remote Similarity	NPD5694	Approved
0.6449	Remote Similarity	NPD8034	Phase 2
0.6446	Remote Similarity	NPD6335	Approved
0.6442	Remote Similarity	NPD6098	Approved
0.6436	Remote Similarity	NPD5369	Approved
0.6423	Remote Similarity	NPD8517	Approved
0.6423	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6423	Remote Similarity	NPD8516	Approved
0.6423	Remote Similarity	NPD8515	Approved
0.6423	Remote Similarity	NPD8513	Phase 3
0.6417	Remote Similarity	NPD6274	Approved
0.6417	Remote Similarity	NPD6868	Approved
0.641	Remote Similarity	NPD5247	Approved
0.641	Remote Similarity	NPD5135	Approved
0.641	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.641	Remote Similarity	NPD5248	Approved
0.641	Remote Similarity	NPD5249	Phase 3
0.641	Remote Similarity	NPD5250	Approved
0.641	Remote Similarity	NPD5251	Approved
0.641	Remote Similarity	NPD5169	Approved
0.6406	Remote Similarity	NPD5956	Approved
0.6406	Remote Similarity	NPD6914	Discontinued
0.64	Remote Similarity	NPD4195	Approved
0.6393	Remote Similarity	NPD7100	Approved
0.6393	Remote Similarity	NPD7101	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