NPASS Compound

Structure

NPC476021 OpenBabel07101718312D 32 37 0 0 1 0 0 0 0 0999 V2000 -1.5606 -7.1971 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1645 -6.6760 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9588 -5.3450 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8658 -3.3767 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2904 -2.8369 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8432 -1.4605 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5627 -4.8239 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2619 -3.8979 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1848 -1.4605 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6125 -0.6728 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8432 -3.4079 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8432 -2.4342 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8432 -2.4342 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.9474 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8432 -3.4079 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2121 -6.4735 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9112 -5.5475 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -2.9134 -3.1743 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -3.8947 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.6125 -2.2483 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.6865 -0.9737 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.6865 -0.9737 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.6865 -1.9474 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6865 -1.9474 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -1.9474 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8432 -2.4342 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -0.9737 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8432 -0.4868 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -4.8684 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3729 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6865 -2.9211 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 16 1 0 0 0 0 2 16 1 0 0 0 0 3 17 1 0 0 0 0 6 25 1 0 0 0 0 7 8 2 0 0 0 0 7 17 1 0 0 0 0 8 18 1 0 0 0 0 9 10 1 0 0 0 0 9 20 1 0 0 0 0 10 21 1 0 0 0 0 11 12 1 0 0 0 0 11 19 1 0 0 0 0 12 25 1 0 0 0 0 13 14 1 0 0 0 0 13 24 1 0 0 0 0 14 27 1 0 0 0 0 15 19 1 0 0 0 0 16 17 1 0 0 0 0 18 4 1 1 0 0 0 18 20 1 0 0 0 0 19 29 1 6 0 0 0 20 24 1 1 0 0 0 21 24 1 1 0 0 0 22 23 1 0 0 0 0 22 28 1 1 0 0 0 22 30 1 0 0 0 0 23 26 1 6 0 0 0 23 31 1 0 0 0 0 24 5 1 1 0 0 0 25 26 1 6 0 0 0 25 27 1 0 0 0 0 26 15 1 6 0 0 0 26 31 1 0 0 0 0 27 28 1 6 0 0 0 27 32 1 0 0 0 0 28 21 1 6 0 0 0 28 32 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	444.32
Volume:	474.03
LogP:	4.441
LogD:	4.537
LogS:	-4.823
# Rotatable Bonds:	4
TPSA:	65.52
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	6
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.48
Synthetic Accessibility Score:	6.009
Fsp3:	0.929
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:	-4.888
MDCK Permeability:	2.3203469027066603e-05
Pgp-inhibitor:	0.002
Pgp-substrate:	0.988
Human Intestinal Absorption (HIA):	0.014
20% Bioavailability (F20%):	0.219
30% Bioavailability (F30%):	0.445

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.241
Plasma Protein Binding (PPB):	91.44668579101562%
Volume Distribution (VD):	1.048
Pgp-substrate:	1.927103042602539%

ADMET: Metabolism

CYP1A2-inhibitor:	0.025
CYP1A2-substrate:	0.971
CYP2C19-inhibitor:	0.02
CYP2C19-substrate:	0.917
CYP2C9-inhibitor:	0.132
CYP2C9-substrate:	0.013
CYP2D6-inhibitor:	0.004
CYP2D6-substrate:	0.101
CYP3A4-inhibitor:	0.694
CYP3A4-substrate:	0.914

ADMET: Excretion

Clearance (CL):	4.866
Half-life (T1/2):	0.358

ADMET: Toxicity

hERG Blockers:	0.41
Human Hepatotoxicity (H-HT):	0.909
Drug-inuced Liver Injury (DILI):	0.016
AMES Toxicity:	0.006
Rat Oral Acute Toxicity:	0.882
Maximum Recommended Daily Dose:	0.958
Skin Sensitization:	0.065
Carcinogencity:	0.059
Eye Corrosion:	0.003
Eye Irritation:	0.023
Respiratory Toxicity:	0.974

Download Data

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

Natural Product: NPC476021

Natural Product ID:	NPC476021
*Common Name:**	KAQBBVJKPGNKRN-FADQYDIMSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	KAQBBVJKPGNKRN-FADQYDIMSA-N
Standard InCHI:	InChI=1S/C28H44O4/c1-16(2)17(3)7-8-18(4)20-9-10-21-24(20,5)13-14-27-25(6)12-11-19(29)15-26(25)23(31-26)22(30)28(21,27)32-27/h7-8,16-23,29-30H,9-15H2,1-6H3/b8-7+/t17?,18-,19+,20-,21-,22-,23+,24-,25+,26+,27+,28-/m1/s1
SMILES:	O[C@H]1CC[C@]2([C@@]3(C1)O[C@H]3[C@H]([C@]13[C@@]2(CC[C@]2([C@H]3CC[C@@H]2[C@@H](/C=C/C(C(C)C)C)C)C)O1)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL522113
PubChem CID:	44566286
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0003567] Ergostane steroids

*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
NPO32920	homaxinella sp.	Species	n.a.	Eukaryota	n.a.	n.a.	n.a.	PMID[16441084]
NPO32920	homaxinella sp.	Species	n.a.	Eukaryota	n.a.	n.a.	n.a.	PMID[9834174]

☑ 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
ED50	5

Activity Type	# Activity
Cell Line	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	ED50	=	7.1	ug ml-1	PMID[454037]
NPT146	Cell Line	SK-OV-3	Homo sapiens	ED50	=	6.3	ug ml-1	PMID[454037]
NPT147	Cell Line	SK-MEL-2	Homo sapiens	ED50	=	2.7	ug ml-1	PMID[454037]
NPT574	Cell Line	XF498	Homo sapiens	ED50	=	3.4	ug ml-1	PMID[454037]
NPT148	Cell Line	HCT-15	Homo sapiens	ED50	=	4.8	ug ml-1	PMID[454037]

☑ 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 NPC476021 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	250
0.1-0.2	1897
0.2-0.3	6457
0.3-0.4	14510
0.4-0.5	8709
0.5-0.6	5251
0.6-0.7	4712
0.7-0.8	870
0.8-0.85	32
0.85-0.9	6
0.9-0.95	0
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC476040
1.0	High Similarity	NPC474994
0.8947	High Similarity	NPC316604
0.8804	High Similarity	NPC109744
0.871	High Similarity	NPC475751
0.871	High Similarity	NPC473956
0.8646	High Similarity	NPC210717
0.8646	High Similarity	NPC103165
0.8646	High Similarity	NPC471903
0.8617	High Similarity	NPC210268
0.8617	High Similarity	NPC275671
0.8587	High Similarity	NPC186145
0.8587	High Similarity	NPC474657
0.8557	High Similarity	NPC261807
0.8526	High Similarity	NPC119379
0.8495	Intermediate Similarity	NPC473436
0.8495	Intermediate Similarity	NPC475664
0.8478	Intermediate Similarity	NPC269058
0.8478	Intermediate Similarity	NPC125399
0.8478	Intermediate Similarity	NPC71520
0.8478	Intermediate Similarity	NPC6605
0.8469	Intermediate Similarity	NPC300179
0.8469	Intermediate Similarity	NPC102426
0.8462	Intermediate Similarity	NPC86238
0.8352	Intermediate Similarity	NPC216420
0.8352	Intermediate Similarity	NPC85095
0.8352	Intermediate Similarity	NPC207013
0.8352	Intermediate Similarity	NPC211135
0.8351	Intermediate Similarity	NPC8774
0.83	Intermediate Similarity	NPC476896
0.83	Intermediate Similarity	NPC289670
0.828	Intermediate Similarity	NPC201273
0.8265	Intermediate Similarity	NPC288970
0.8265	Intermediate Similarity	NPC72204
0.8265	Intermediate Similarity	NPC227583
0.8265	Intermediate Similarity	NPC98457
0.8265	Intermediate Similarity	NPC12103
0.8247	Intermediate Similarity	NPC65402
0.8247	Intermediate Similarity	NPC127718
0.8229	Intermediate Similarity	NPC219516
0.8229	Intermediate Similarity	NPC114389
0.8229	Intermediate Similarity	NPC41554
0.8229	Intermediate Similarity	NPC97404
0.8222	Intermediate Similarity	NPC16449
0.82	Intermediate Similarity	NPC324598
0.8191	Intermediate Similarity	NPC189777
0.8182	Intermediate Similarity	NPC477226
0.8152	Intermediate Similarity	NPC141941
0.8152	Intermediate Similarity	NPC193870
0.8152	Intermediate Similarity	NPC477978
0.8152	Intermediate Similarity	NPC113978
0.8144	Intermediate Similarity	NPC98193
0.8144	Intermediate Similarity	NPC137461
0.8125	Intermediate Similarity	NPC204188
0.8125	Intermediate Similarity	NPC3345
0.8125	Intermediate Similarity	NPC291484
0.8125	Intermediate Similarity	NPC80561
0.8125	Intermediate Similarity	NPC11216
0.8125	Intermediate Similarity	NPC10274
0.8125	Intermediate Similarity	NPC329596
0.8119	Intermediate Similarity	NPC309425
0.8119	Intermediate Similarity	NPC160734
0.8119	Intermediate Similarity	NPC47566
0.8119	Intermediate Similarity	NPC88000
0.8119	Intermediate Similarity	NPC129372
0.8119	Intermediate Similarity	NPC4831
0.8119	Intermediate Similarity	NPC472023
0.8105	Intermediate Similarity	NPC133588
0.81	Intermediate Similarity	NPC234287
0.81	Intermediate Similarity	NPC280825
0.81	Intermediate Similarity	NPC5358
0.81	Intermediate Similarity	NPC216260
0.81	Intermediate Similarity	NPC476895
0.8085	Intermediate Similarity	NPC299068
0.8085	Intermediate Similarity	NPC121981
0.8085	Intermediate Similarity	NPC94462
0.8065	Intermediate Similarity	NPC475798
0.8065	Intermediate Similarity	NPC127606
0.8058	Intermediate Similarity	NPC273879
0.8058	Intermediate Similarity	NPC165033
0.8058	Intermediate Similarity	NPC312774
0.8043	Intermediate Similarity	NPC30166
0.8039	Intermediate Similarity	NPC136816
0.8022	Intermediate Similarity	NPC102253
0.8022	Intermediate Similarity	NPC322313
0.8022	Intermediate Similarity	NPC236237
0.8022	Intermediate Similarity	NPC13554
0.8021	Intermediate Similarity	NPC105495
0.8021	Intermediate Similarity	NPC470361
0.802	Intermediate Similarity	NPC473200
0.802	Intermediate Similarity	NPC7341
0.8	Intermediate Similarity	NPC476893
0.8	Intermediate Similarity	NPC475033
0.8	Intermediate Similarity	NPC475032
0.7979	Intermediate Similarity	NPC470360
0.7961	Intermediate Similarity	NPC16573
0.7961	Intermediate Similarity	NPC286969
0.7961	Intermediate Similarity	NPC16520
0.7961	Intermediate Similarity	NPC245280
0.7961	Intermediate Similarity	NPC114874
0.7961	Intermediate Similarity	NPC120123
0.7961	Intermediate Similarity	NPC189852
0.7961	Intermediate Similarity	NPC8039
0.7961	Intermediate Similarity	NPC211879
0.7961	Intermediate Similarity	NPC157659
0.7961	Intermediate Similarity	NPC473020
0.7961	Intermediate Similarity	NPC31907
0.7961	Intermediate Similarity	NPC213190
0.7961	Intermediate Similarity	NPC472252
0.7961	Intermediate Similarity	NPC131479
0.7961	Intermediate Similarity	NPC155010
0.7959	Intermediate Similarity	NPC27531
0.7957	Intermediate Similarity	NPC110778
0.7957	Intermediate Similarity	NPC477818
0.7941	Intermediate Similarity	NPC155974
0.7941	Intermediate Similarity	NPC475617
0.7938	Intermediate Similarity	NPC191323
0.7938	Intermediate Similarity	NPC470832
0.7935	Intermediate Similarity	NPC70927
0.7925	Intermediate Similarity	NPC472901
0.7921	Intermediate Similarity	NPC477875
0.7921	Intermediate Similarity	NPC477876
0.7921	Intermediate Similarity	NPC470068
0.7921	Intermediate Similarity	NPC470066
0.7921	Intermediate Similarity	NPC470067
0.7917	Intermediate Similarity	NPC474668
0.7917	Intermediate Similarity	NPC67872
0.7917	Intermediate Similarity	NPC475605
0.7917	Intermediate Similarity	NPC212596
0.7917	Intermediate Similarity	NPC4574
0.7912	Intermediate Similarity	NPC273410
0.7912	Intermediate Similarity	NPC80530
0.7905	Intermediate Similarity	NPC181467
0.7895	Intermediate Similarity	NPC139724
0.7885	Intermediate Similarity	NPC475365
0.7879	Intermediate Similarity	NPC144202
0.7872	Intermediate Similarity	NPC15534
0.7872	Intermediate Similarity	NPC255882
0.787	Intermediate Similarity	NPC475312
0.7864	Intermediate Similarity	NPC288694
0.7864	Intermediate Similarity	NPC312553
0.7864	Intermediate Similarity	NPC159036
0.7857	Intermediate Similarity	NPC48463
0.785	Intermediate Similarity	NPC472717
0.7843	Intermediate Similarity	NPC208358
0.7843	Intermediate Similarity	NPC317019
0.7835	Intermediate Similarity	NPC101886
0.7835	Intermediate Similarity	NPC138974
0.7835	Intermediate Similarity	NPC128066
0.783	Intermediate Similarity	NPC246124
0.783	Intermediate Similarity	NPC472897
0.783	Intermediate Similarity	NPC472896
0.783	Intermediate Similarity	NPC235824
0.783	Intermediate Similarity	NPC180183
0.7826	Intermediate Similarity	NPC236112
0.7822	Intermediate Similarity	NPC210337
0.7812	Intermediate Similarity	NPC304083
0.7812	Intermediate Similarity	NPC477600
0.7812	Intermediate Similarity	NPC470620
0.781	Intermediate Similarity	NPC208477
0.781	Intermediate Similarity	NPC472898
0.781	Intermediate Similarity	NPC472899
0.781	Intermediate Similarity	NPC69737
0.781	Intermediate Similarity	NPC474015
0.781	Intermediate Similarity	NPC208594
0.781	Intermediate Similarity	NPC473199
0.781	Intermediate Similarity	NPC160816
0.781	Intermediate Similarity	NPC127801
0.781	Intermediate Similarity	NPC194842
0.781	Intermediate Similarity	NPC472900
0.781	Intermediate Similarity	NPC269627
0.781	Intermediate Similarity	NPC152584
0.7802	Intermediate Similarity	NPC138621
0.7802	Intermediate Similarity	NPC471769
0.7802	Intermediate Similarity	NPC167037
0.7802	Intermediate Similarity	NPC31828
0.7802	Intermediate Similarity	NPC147993
0.7802	Intermediate Similarity	NPC285761
0.7802	Intermediate Similarity	NPC244385
0.7802	Intermediate Similarity	NPC6978
0.7789	Intermediate Similarity	NPC290731
0.7789	Intermediate Similarity	NPC474189
0.7789	Intermediate Similarity	NPC474349
0.7788	Intermediate Similarity	NPC473523
0.7788	Intermediate Similarity	NPC473198
0.7788	Intermediate Similarity	NPC475701
0.7788	Intermediate Similarity	NPC474124
0.7778	Intermediate Similarity	NPC310013
0.7778	Intermediate Similarity	NPC472715
0.7778	Intermediate Similarity	NPC472987
0.7778	Intermediate Similarity	NPC473021
0.7778	Intermediate Similarity	NPC307776
0.7767	Intermediate Similarity	NPC470054
0.7767	Intermediate Similarity	NPC476897
0.7766	Intermediate Similarity	NPC82623
0.7766	Intermediate Similarity	NPC470558
0.7766	Intermediate Similarity	NPC232023
0.7766	Intermediate Similarity	NPC470929
0.7766	Intermediate Similarity	NPC134481
0.7757	Intermediate Similarity	NPC43976

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 NPC476021 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	206
0.1-0.2	2073
0.2-0.3	4388
0.3-0.4	1703
0.4-0.5	417
0.5-0.6	188
0.6-0.7	165
0.7-0.8	10
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
0.8022	Intermediate Similarity	NPD7525	Registered
0.7812	Intermediate Similarity	NPD7524	Approved
0.75	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.7456	Intermediate Similarity	NPD7516	Approved
0.7431	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7429	Intermediate Similarity	NPD5344	Discontinued
0.7396	Intermediate Similarity	NPD6695	Phase 3
0.7368	Intermediate Similarity	NPD7328	Approved
0.7368	Intermediate Similarity	NPD7327	Approved
0.7228	Intermediate Similarity	NPD3168	Discontinued
0.7158	Intermediate Similarity	NPD7645	Phase 2
0.7128	Intermediate Similarity	NPD6932	Approved
0.7111	Intermediate Similarity	NPD4267	Clinical (unspecified phase)
0.71	Intermediate Similarity	NPD7750	Discontinued
0.7097	Intermediate Similarity	NPD6942	Approved
0.7097	Intermediate Similarity	NPD7339	Approved
0.7083	Intermediate Similarity	NPD6930	Phase 2
0.7083	Intermediate Similarity	NPD6931	Approved
0.7075	Intermediate Similarity	NPD7638	Approved
0.7054	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7034	Intermediate Similarity	NPD8379	Approved
0.7034	Intermediate Similarity	NPD8378	Approved
0.7034	Intermediate Similarity	NPD8296	Approved
0.7034	Intermediate Similarity	NPD8380	Approved
0.7034	Intermediate Similarity	NPD8335	Approved
0.7021	Intermediate Similarity	NPD6933	Approved
0.7009	Intermediate Similarity	NPD6648	Approved
0.7009	Intermediate Similarity	NPD7639	Approved
0.7009	Intermediate Similarity	NPD7640	Approved
0.6979	Remote Similarity	NPD6929	Approved
0.6949	Remote Similarity	NPD8294	Approved
0.6949	Remote Similarity	NPD8377	Approved
0.6944	Remote Similarity	NPD4159	Approved
0.6907	Remote Similarity	NPD7514	Phase 3
0.6891	Remote Similarity	NPD8033	Approved
0.6875	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD7145	Approved
0.687	Remote Similarity	NPD4632	Approved
0.6842	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6838	Remote Similarity	NPD7115	Discovery
0.6837	Remote Similarity	NPD6902	Approved
0.6827	Remote Similarity	NPD7087	Discontinued
0.6809	Remote Similarity	NPD6926	Approved
0.6809	Remote Similarity	NPD6924	Approved
0.6807	Remote Similarity	NPD6054	Approved
0.6807	Remote Similarity	NPD6319	Approved
0.6804	Remote Similarity	NPD6683	Phase 2
0.6786	Remote Similarity	NPD6412	Phase 2
0.6786	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6783	Remote Similarity	NPD8297	Approved
0.6771	Remote Similarity	NPD5776	Phase 2
0.6771	Remote Similarity	NPD6925	Approved
0.6765	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6754	Remote Similarity	NPD4634	Approved
0.675	Remote Similarity	NPD7503	Approved
0.6735	Remote Similarity	NPD7332	Phase 2
0.6733	Remote Similarity	NPD6893	Approved
0.6726	Remote Similarity	NPD6881	Approved
0.6726	Remote Similarity	NPD6899	Approved
0.6697	Remote Similarity	NPD5285	Approved
0.6697	Remote Similarity	NPD5286	Approved
0.6697	Remote Similarity	NPD4696	Approved
0.6696	Remote Similarity	NPD6675	Approved
0.6696	Remote Similarity	NPD7128	Approved
0.6696	Remote Similarity	NPD6402	Approved
0.6696	Remote Similarity	NPD5357	Phase 1
0.6696	Remote Similarity	NPD5739	Approved
0.6694	Remote Similarity	NPD6370	Approved
0.6667	Remote Similarity	NPD6059	Approved
0.6667	Remote Similarity	NPD4755	Approved
0.6667	Remote Similarity	NPD6079	Approved
0.6667	Remote Similarity	NPD7507	Approved
0.664	Remote Similarity	NPD7319	Approved
0.6639	Remote Similarity	NPD7604	Phase 2
0.6637	Remote Similarity	NPD5697	Approved
0.6635	Remote Similarity	NPD5328	Approved
0.6634	Remote Similarity	NPD4786	Approved
0.6632	Remote Similarity	NPD4784	Approved
0.6632	Remote Similarity	NPD4785	Approved
0.6612	Remote Similarity	NPD6015	Approved
0.6612	Remote Similarity	NPD6016	Approved
0.6609	Remote Similarity	NPD7290	Approved
0.6609	Remote Similarity	NPD7102	Approved
0.6609	Remote Similarity	NPD6883	Approved
0.6604	Remote Similarity	NPD4202	Approved
0.6604	Remote Similarity	NPD6399	Phase 3
0.6596	Remote Similarity	NPD4243	Approved
0.6596	Remote Similarity	NPD7150	Approved
0.6596	Remote Similarity	NPD7152	Approved
0.6596	Remote Similarity	NPD7151	Approved
0.6585	Remote Similarity	NPD7492	Approved
0.6579	Remote Similarity	NPD7320	Approved
0.6577	Remote Similarity	NPD4633	Approved
0.6577	Remote Similarity	NPD5225	Approved
0.6577	Remote Similarity	NPD3653	Clinical (unspecified phase)
0.6577	Remote Similarity	NPD5224	Approved
0.6577	Remote Similarity	NPD5226	Approved
0.6577	Remote Similarity	NPD5211	Phase 2
0.6566	Remote Similarity	NPD7509	Discontinued
0.656	Remote Similarity	NPD7736	Approved
0.6557	Remote Similarity	NPD5988	Approved
0.6555	Remote Similarity	NPD6009	Approved
0.6552	Remote Similarity	NPD6869	Approved
0.6552	Remote Similarity	NPD6617	Approved
0.6552	Remote Similarity	NPD6847	Approved
0.6552	Remote Similarity	NPD8130	Phase 1
0.6552	Remote Similarity	NPD6649	Approved
0.6552	Remote Similarity	NPD6650	Approved
0.6549	Remote Similarity	NPD6008	Approved
0.6545	Remote Similarity	NPD4700	Approved
0.6532	Remote Similarity	NPD6616	Approved
0.6522	Remote Similarity	NPD6014	Approved
0.6522	Remote Similarity	NPD6373	Approved
0.6522	Remote Similarity	NPD6012	Approved
0.6522	Remote Similarity	NPD6372	Approved
0.6522	Remote Similarity	NPD6013	Approved
0.6518	Remote Similarity	NPD5174	Approved
0.6518	Remote Similarity	NPD5175	Approved
0.6509	Remote Similarity	NPD8034	Phase 2
0.6509	Remote Similarity	NPD8035	Phase 2
0.6509	Remote Similarity	NPD7637	Suspended
0.6505	Remote Similarity	NPD3618	Phase 1
0.65	Remote Similarity	NPD6898	Phase 1
0.6496	Remote Similarity	NPD6882	Approved
0.6491	Remote Similarity	NPD5701	Approved
0.6489	Remote Similarity	NPD7143	Approved
0.6489	Remote Similarity	NPD7144	Approved
0.6486	Remote Similarity	NPD5223	Approved
0.648	Remote Similarity	NPD7078	Approved
0.6475	Remote Similarity	NPD5983	Phase 2
0.646	Remote Similarity	NPD5141	Approved
0.6449	Remote Similarity	NPD8171	Discontinued
0.6441	Remote Similarity	NPD8133	Approved
0.6436	Remote Similarity	NPD3667	Approved
0.6435	Remote Similarity	NPD6011	Approved
0.6429	Remote Similarity	NPD7632	Discontinued
0.6422	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6422	Remote Similarity	NPD5222	Approved
0.6422	Remote Similarity	NPD5221	Approved
0.6408	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.64	Remote Similarity	NPD6928	Phase 2
0.64	Remote Similarity	NPD4748	Discontinued
0.64	Remote Similarity	NPD6336	Discontinued
0.6383	Remote Similarity	NPD6923	Approved
0.6383	Remote Similarity	NPD6922	Approved
0.6379	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6374	Remote Similarity	NPD371	Approved
0.6364	Remote Similarity	NPD6083	Phase 2
0.6364	Remote Similarity	NPD6084	Phase 2
0.6364	Remote Similarity	NPD5173	Approved
0.6349	Remote Similarity	NPD8293	Discontinued
0.6321	Remote Similarity	NPD4753	Phase 2
0.6306	Remote Similarity	NPD4225	Approved
0.63	Remote Similarity	NPD4195	Approved
0.6293	Remote Similarity	NPD4730	Approved
0.6293	Remote Similarity	NPD6686	Approved
0.6293	Remote Similarity	NPD4729	Approved
0.6273	Remote Similarity	NPD4697	Phase 3
0.6271	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6261	Remote Similarity	NPD4768	Approved
0.6261	Remote Similarity	NPD4767	Approved
0.6239	Remote Similarity	NPD7748	Approved
0.6228	Remote Similarity	NPD4754	Approved
0.6224	Remote Similarity	NPD4190	Phase 3
0.6224	Remote Similarity	NPD5275	Approved
0.6216	Remote Similarity	NPD7902	Approved
0.621	Remote Similarity	NPD6921	Approved
0.6204	Remote Similarity	NPD7515	Phase 2
0.62	Remote Similarity	NPD6697	Approved
0.62	Remote Similarity	NPD6114	Approved
0.62	Remote Similarity	NPD6115	Approved
0.62	Remote Similarity	NPD6118	Approved
0.62	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6186	Remote Similarity	NPD5249	Phase 3
0.6186	Remote Similarity	NPD5248	Approved
0.6186	Remote Similarity	NPD5247	Approved
0.6186	Remote Similarity	NPD5251	Approved
0.6186	Remote Similarity	NPD5250	Approved
0.6182	Remote Similarity	NPD4629	Approved
0.6182	Remote Similarity	NPD5210	Approved
0.6179	Remote Similarity	NPD7100	Approved
0.6179	Remote Similarity	NPD7101	Approved
0.6172	Remote Similarity	NPD6033	Approved
0.6168	Remote Similarity	NPD6051	Approved
0.6154	Remote Similarity	NPD3665	Phase 1
0.6154	Remote Similarity	NPD3133	Approved
0.6154	Remote Similarity	NPD5128	Approved
0.6154	Remote Similarity	NPD3666	Approved
0.6146	Remote Similarity	NPD4787	Phase 1
0.6134	Remote Similarity	NPD5216	Approved
0.6134	Remote Similarity	NPD5215	Approved
0.6134	Remote Similarity	NPD5217	Approved
0.6129	Remote Similarity	NPD7741	Discontinued
0.6121	Remote Similarity	NPD6640	Phase 3
0.6111	Remote Similarity	NPD8328	Phase 3
0.6111	Remote Similarity	NPD7136	Phase 2
0.6111	Remote Similarity	NPD6067	Discontinued
0.61	Remote Similarity	NPD6116	Phase 1
0.6098	Remote Similarity	NPD6335	Approved
0.6066	Remote Similarity	NPD6274	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