NPASS Compound

Structure

NPC471111 OpenBabel07101719252D 36 42 0 0 1 0 0 0 0 0999 V2000 1.5600 2.8838 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2941 -3.0138 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2941 -3.0138 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2020 -0.7067 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2074 -0.8112 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7367 -1.0613 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7367 1.7658 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0620 -2.1478 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1960 -1.6478 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6601 -0.6478 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7941 -0.1478 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0223 2.1793 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0620 0.8522 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9281 0.3522 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9722 2.0748 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.6101 1.3703 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.9281 -1.6478 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.1960 -0.6478 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6601 -1.6478 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.1960 1.3522 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.3789 1.1613 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.7006 0.5090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.3789 -0.4568 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.7941 -2.1478 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6142 0.1023 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3300 -0.1478 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.3300 0.8522 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.9281 -0.6478 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.0620 -0.1478 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.7912 0.3522 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 7.5261 -2.1478 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.1960 2.3522 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.0699 -1.4078 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4232 0.6901 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.2034 0.4568 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 2 24 1 0 0 0 0 3 24 1 0 0 0 0 4 25 1 0 0 0 0 5 25 1 0 0 0 0 6 26 1 0 0 0 0 8 9 1 0 0 0 0 8 17 1 0 0 0 0 9 18 2 0 0 0 0 10 11 1 0 0 0 0 10 19 1 0 0 0 0 11 28 1 0 0 0 0 12 15 1 0 0 0 0 13 20 1 0 0 0 0 14 28 1 0 0 0 0 14 29 1 0 0 0 0 15 1 1 1 0 0 0 15 21 1 0 0 0 0 16 12 1 1 0 0 0 16 22 1 0 0 0 0 16 35 1 0 0 0 0 17 24 1 0 0 0 0 17 28 1 6 0 0 0 18 26 1 0 0 0 0 18 29 1 0 0 0 0 19 24 1 0 0 0 0 19 31 1 6 0 0 0 20 27 1 6 0 0 0 20 32 1 0 0 0 0 21 27 1 6 0 0 0 21 30 1 0 0 0 0 22 25 1 6 0 0 0 22 36 1 0 0 0 0 23 26 1 1 0 0 0 23 30 1 0 0 0 0 23 33 1 0 0 0 0 25 34 1 0 0 0 0 26 27 1 1 0 0 0 27 7 1 6 0 0 0 28 29 1 1 0 0 0 29 13 1 1 0 0 0 30 35 1 1 0 0 0 30 36 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	502.33
Volume:	517.646
LogP:	3.805
LogD:	3.051
LogS:	-4.002
# Rotatable Bonds:	1
TPSA:	99.38
# H-Bond Aceptor:	6
# H-Bond Donor:	4
# Rings:	7
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.41
Synthetic Accessibility Score:	7.343
Fsp3:	0.933
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.312
MDCK Permeability:	1.1898518096131738e-05
Pgp-inhibitor:	0.005
Pgp-substrate:	0.01
Human Intestinal Absorption (HIA):	0.014
20% Bioavailability (F20%):	0.2
30% Bioavailability (F30%):	0.897

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.259
Plasma Protein Binding (PPB):	72.64412689208984%
Volume Distribution (VD):	0.938
Pgp-substrate:	22.162092208862305%

ADMET: Metabolism

CYP1A2-inhibitor:	0.002
CYP1A2-substrate:	0.34
CYP2C19-inhibitor:	0.007
CYP2C19-substrate:	0.77
CYP2C9-inhibitor:	0.042
CYP2C9-substrate:	0.038
CYP2D6-inhibitor:	0.003
CYP2D6-substrate:	0.117
CYP3A4-inhibitor:	0.727
CYP3A4-substrate:	0.23

ADMET: Excretion

Clearance (CL):	3.05
Half-life (T1/2):	0.526

ADMET: Toxicity

hERG Blockers:	0.466
Human Hepatotoxicity (H-HT):	0.975
Drug-inuced Liver Injury (DILI):	0.078
AMES Toxicity:	0.018
Rat Oral Acute Toxicity:	0.993
Maximum Recommended Daily Dose:	0.994
Skin Sensitization:	0.754
Carcinogencity:	0.032
Eye Corrosion:	0.004
Eye Irritation:	0.018
Respiratory Toxicity:	0.986

Download Data

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

Natural Product: NPC471111

Natural Product ID:	NPC471111
*Common Name:**	FHFYINZDHOGLRJ-DXPCVWRCSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	FHFYINZDHOGLRJ-DXPCVWRCSA-N
Standard InCHI:	InChI=1S/C30H46O6/c1-15-12-16-22(25(4,5)34)36-30(35-16)21(15)27(7)20(32)13-29-14-28(29)11-10-19(31)24(2,3)17(28)8-9-18(29)26(27,6)23(30)33/h9,15-17,19-23,31-34H,8,10-14H2,1-7H3/t15-,16-,17+,19+,20-,21-,22+,23-,26-,27-,28-,29+,30-/m1/s1
SMILES:	C[C@@H]1C[C@H]2O[C@]3([C@H]1[C@@]1(C)[C@H](O)C[C@@]45C(=CC[C@@H]6[C@]5(C4)CC[C@@H](C6(C)C)O)[C@@]1([C@H]3O)C)O[C@@H]2C(O)(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2375500
PubChem CID:	73348790
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0002321] Cycloartanols 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
NPO33019	cimicifuga yunnanensis	Species	Ranunculaceae	Eukaryota	aerial parts	n.a.	n.a.	PMID[23621813]

☑ 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

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1893	Cell Line	MEF	Mus musculus	IC50	=	9800.0	nM	PMID[551354]

☑ 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 NPC471111 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	270
0.1-0.2	2056
0.2-0.3	6825
0.3-0.4	14318
0.4-0.5	7793
0.5-0.6	5167
0.6-0.7	4505
0.7-0.8	1530
0.8-0.85	197
0.85-0.9	28
0.9-0.95	6
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9691	High Similarity	NPC475701
0.9592	High Similarity	NPC474464
0.9495	High Similarity	NPC474015
0.9278	High Similarity	NPC275865
0.9216	High Similarity	NPC476835
0.9216	High Similarity	NPC128133
0.9192	High Similarity	NPC22634
0.9109	High Similarity	NPC26798
0.9091	High Similarity	NPC474022
0.9038	High Similarity	NPC197231
0.902	High Similarity	NPC226642
0.898	High Similarity	NPC177818
0.8952	High Similarity	NPC19888
0.8889	High Similarity	NPC309493
0.8889	High Similarity	NPC216260
0.8889	High Similarity	NPC5358
0.8846	High Similarity	NPC40440
0.8846	High Similarity	NPC42482
0.88	High Similarity	NPC324598
0.8763	High Similarity	NPC235126
0.8763	High Similarity	NPC242419
0.8763	High Similarity	NPC98193
0.875	High Similarity	NPC476539
0.875	High Similarity	NPC476541
0.875	High Similarity	NPC7213
0.875	High Similarity	NPC476540
0.875	High Similarity	NPC476538
0.8738	High Similarity	NPC242748
0.8738	High Similarity	NPC474569
0.8738	High Similarity	NPC181845
0.8725	High Similarity	NPC213190
0.8713	High Similarity	NPC471112
0.8713	High Similarity	NPC176406
0.8704	High Similarity	NPC212660
0.8692	High Similarity	NPC178981
0.8679	High Similarity	NPC477028
0.8679	High Similarity	NPC477032
0.8679	High Similarity	NPC124677
0.8667	High Similarity	NPC477027
0.8667	High Similarity	NPC306131
0.8667	High Similarity	NPC477026
0.8667	High Similarity	NPC70204
0.8667	High Similarity	NPC475670
0.8654	High Similarity	NPC470432
0.8654	High Similarity	NPC161676
0.8654	High Similarity	NPC305423
0.8654	High Similarity	NPC283829
0.8654	High Similarity	NPC113044
0.8654	High Similarity	NPC14704
0.8654	High Similarity	NPC230507
0.8641	High Similarity	NPC475365
0.8641	High Similarity	NPC221562
0.8641	High Similarity	NPC187400
0.8641	High Similarity	NPC470885
0.8627	High Similarity	NPC136816
0.8611	High Similarity	NPC167183
0.8611	High Similarity	NPC477810
0.8611	High Similarity	NPC32707
0.86	High Similarity	NPC473890
0.86	High Similarity	NPC243728
0.8598	High Similarity	NPC254255
0.8598	High Similarity	NPC477050
0.8571	High Similarity	NPC98696
0.8558	High Similarity	NPC473476
0.8558	High Similarity	NPC473923
0.8529	High Similarity	NPC73385
0.8529	High Similarity	NPC472023
0.8529	High Similarity	NPC88000
0.8529	High Similarity	NPC129372
0.8529	High Similarity	NPC160734
0.8529	High Similarity	NPC47566
0.8529	High Similarity	NPC4831
0.8529	High Similarity	NPC476896
0.8529	High Similarity	NPC309425
0.8519	High Similarity	NPC144068
0.8519	High Similarity	NPC476693
0.8519	High Similarity	NPC79900
0.8515	High Similarity	NPC280825
0.8515	High Similarity	NPC234287
0.8515	High Similarity	NPC476895
0.8515	High Similarity	NPC158088
0.8505	High Similarity	NPC13193
0.8505	High Similarity	NPC294129
0.8505	High Similarity	NPC476547
0.8505	High Similarity	NPC13190
0.8505	High Similarity	NPC475247
0.85	High Similarity	NPC207617
0.8491	Intermediate Similarity	NPC208383
0.8491	Intermediate Similarity	NPC309278
0.8491	Intermediate Similarity	NPC95051
0.8491	Intermediate Similarity	NPC171073
0.8491	Intermediate Similarity	NPC194207
0.8491	Intermediate Similarity	NPC470433
0.8491	Intermediate Similarity	NPC475333
0.8491	Intermediate Similarity	NPC300557
0.8491	Intermediate Similarity	NPC477809
0.8491	Intermediate Similarity	NPC218571
0.8491	Intermediate Similarity	NPC248746
0.8491	Intermediate Similarity	NPC244086
0.8491	Intermediate Similarity	NPC150372
0.8491	Intermediate Similarity	NPC232054
0.8491	Intermediate Similarity	NPC249265
0.8491	Intermediate Similarity	NPC84956
0.8491	Intermediate Similarity	NPC102016
0.8491	Intermediate Similarity	NPC46190
0.8491	Intermediate Similarity	NPC22779
0.8491	Intermediate Similarity	NPC475550
0.8491	Intermediate Similarity	NPC6806
0.8491	Intermediate Similarity	NPC73243
0.8491	Intermediate Similarity	NPC224098
0.8476	Intermediate Similarity	NPC473469
0.8476	Intermediate Similarity	NPC190395
0.8462	Intermediate Similarity	NPC85593
0.8462	Intermediate Similarity	NPC75608
0.8462	Intermediate Similarity	NPC312774
0.8462	Intermediate Similarity	NPC31430
0.8454	Intermediate Similarity	NPC228059
0.8431	Intermediate Similarity	NPC7341
0.8431	Intermediate Similarity	NPC282669
0.8431	Intermediate Similarity	NPC471242
0.8431	Intermediate Similarity	NPC473790
0.8431	Intermediate Similarity	NPC473200
0.8426	Intermediate Similarity	NPC473567
0.8426	Intermediate Similarity	NPC244431
0.8426	Intermediate Similarity	NPC216595
0.8426	Intermediate Similarity	NPC112274
0.8426	Intermediate Similarity	NPC32361
0.8426	Intermediate Similarity	NPC31896
0.8426	Intermediate Similarity	NPC210569
0.8426	Intermediate Similarity	NPC263359
0.8416	Intermediate Similarity	NPC76486
0.8416	Intermediate Similarity	NPC476893
0.8411	Intermediate Similarity	NPC247037
0.8411	Intermediate Similarity	NPC141433
0.8411	Intermediate Similarity	NPC191439
0.8411	Intermediate Similarity	NPC269297
0.8411	Intermediate Similarity	NPC170974
0.8411	Intermediate Similarity	NPC222202
0.8411	Intermediate Similarity	NPC87998
0.8411	Intermediate Similarity	NPC224314
0.8411	Intermediate Similarity	NPC103627
0.8411	Intermediate Similarity	NPC477811
0.8411	Intermediate Similarity	NPC23808
0.8396	Intermediate Similarity	NPC476513
0.8396	Intermediate Similarity	NPC220427
0.8381	Intermediate Similarity	NPC472900
0.8381	Intermediate Similarity	NPC472898
0.8381	Intermediate Similarity	NPC309448
0.8381	Intermediate Similarity	NPC472899
0.8365	Intermediate Similarity	NPC211879
0.8365	Intermediate Similarity	NPC286969
0.8365	Intermediate Similarity	NPC16520
0.8365	Intermediate Similarity	NPC114874
0.8365	Intermediate Similarity	NPC8039
0.8365	Intermediate Similarity	NPC120123
0.8365	Intermediate Similarity	NPC131479
0.8365	Intermediate Similarity	NPC473020
0.8365	Intermediate Similarity	NPC245280
0.8365	Intermediate Similarity	NPC155010
0.8365	Intermediate Similarity	NPC473198
0.8365	Intermediate Similarity	NPC189852
0.8365	Intermediate Similarity	NPC31907
0.8365	Intermediate Similarity	NPC157659
0.8365	Intermediate Similarity	NPC472252
0.8364	Intermediate Similarity	NPC477031
0.835	Intermediate Similarity	NPC470434
0.835	Intermediate Similarity	NPC470054
0.835	Intermediate Similarity	NPC31346
0.835	Intermediate Similarity	NPC267510
0.8349	Intermediate Similarity	NPC51154
0.8333	Intermediate Similarity	NPC114188
0.8333	Intermediate Similarity	NPC208189
0.8333	Intermediate Similarity	NPC65034
0.8318	Intermediate Similarity	NPC250089
0.8318	Intermediate Similarity	NPC473328
0.8318	Intermediate Similarity	NPC28844
0.8318	Intermediate Similarity	NPC157530
0.8318	Intermediate Similarity	NPC302057
0.8318	Intermediate Similarity	NPC14630
0.8318	Intermediate Similarity	NPC473318
0.8318	Intermediate Similarity	NPC472901
0.8302	Intermediate Similarity	NPC33053
0.8302	Intermediate Similarity	NPC94272
0.83	Intermediate Similarity	NPC477927
0.83	Intermediate Similarity	NPC305160
0.83	Intermediate Similarity	NPC72817
0.8288	Intermediate Similarity	NPC203862
0.8286	Intermediate Similarity	NPC470059
0.8286	Intermediate Similarity	NPC273879
0.8286	Intermediate Similarity	NPC470057
0.8286	Intermediate Similarity	NPC165033
0.8286	Intermediate Similarity	NPC470043
0.8286	Intermediate Similarity	NPC470062
0.8286	Intermediate Similarity	NPC470064
0.8286	Intermediate Similarity	NPC470060
0.8286	Intermediate Similarity	NPC470061
0.8286	Intermediate Similarity	NPC470058
0.8286	Intermediate Similarity	NPC93352
0.8283	Intermediate Similarity	NPC210268
0.8273	Intermediate Similarity	NPC11548

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 NPC471111 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	220
0.1-0.2	2242
0.2-0.3	4351
0.3-0.4	1552
0.4-0.5	399
0.5-0.6	213
0.6-0.7	140
0.7-0.8	33
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
0.7895	Intermediate Similarity	NPD7327	Approved
0.7895	Intermediate Similarity	NPD7328	Approved
0.7845	Intermediate Similarity	NPD8033	Approved
0.7826	Intermediate Similarity	NPD7516	Approved
0.7798	Intermediate Similarity	NPD6412	Phase 2
0.7759	Intermediate Similarity	NPD6059	Approved
0.7759	Intermediate Similarity	NPD8377	Approved
0.7759	Intermediate Similarity	NPD8294	Approved
0.7759	Intermediate Similarity	NPD6054	Approved
0.7692	Intermediate Similarity	NPD8378	Approved
0.7692	Intermediate Similarity	NPD8335	Approved
0.7692	Intermediate Similarity	NPD8296	Approved
0.7692	Intermediate Similarity	NPD8380	Approved
0.7692	Intermediate Similarity	NPD8379	Approved
0.7627	Intermediate Similarity	NPD6370	Approved
0.7542	Intermediate Similarity	NPD6016	Approved
0.7542	Intermediate Similarity	NPD7503	Approved
0.7542	Intermediate Similarity	NPD6015	Approved
0.7526	Intermediate Similarity	NPD6928	Phase 2
0.75	Intermediate Similarity	NPD7492	Approved
0.75	Intermediate Similarity	NPD8171	Discontinued
0.7479	Intermediate Similarity	NPD5988	Approved
0.7459	Intermediate Similarity	NPD7736	Approved
0.7438	Intermediate Similarity	NPD7507	Approved
0.7438	Intermediate Similarity	NPD6616	Approved
0.7377	Intermediate Similarity	NPD7078	Approved
0.7377	Intermediate Similarity	NPD8293	Discontinued
0.7347	Intermediate Similarity	NPD7525	Registered
0.7258	Intermediate Similarity	NPD7319	Approved
0.7184	Intermediate Similarity	NPD7524	Approved
0.7177	Intermediate Similarity	NPD6033	Approved
0.7131	Intermediate Similarity	NPD6067	Discontinued
0.7113	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7087	Intermediate Similarity	NPD8449	Approved
0.708	Intermediate Similarity	NPD6008	Approved
0.7059	Intermediate Similarity	NPD6009	Approved
0.7059	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.7043	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7031	Intermediate Similarity	NPD8450	Suspended
0.7025	Intermediate Similarity	NPD6319	Approved
0.7019	Intermediate Similarity	NPD4751	Clinical (unspecified phase)
0.701	Intermediate Similarity	NPD7339	Approved
0.701	Intermediate Similarity	NPD6942	Approved
0.7009	Intermediate Similarity	NPD6882	Approved
0.6961	Remote Similarity	NPD6695	Phase 3
0.6957	Remote Similarity	NPD7320	Approved
0.6949	Remote Similarity	NPD4632	Approved
0.6949	Remote Similarity	NPD8133	Approved
0.693	Remote Similarity	NPD7128	Approved
0.693	Remote Similarity	NPD6402	Approved
0.693	Remote Similarity	NPD6675	Approved
0.693	Remote Similarity	NPD5739	Approved
0.69	Remote Similarity	NPD7645	Phase 2
0.6875	Remote Similarity	NPD4159	Approved
0.6864	Remote Similarity	NPD8297	Approved
0.6855	Remote Similarity	NPD7604	Phase 2
0.6847	Remote Similarity	NPD7638	Approved
0.6842	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6838	Remote Similarity	NPD4634	Approved
0.6832	Remote Similarity	NPD4748	Discontinued
0.681	Remote Similarity	NPD6899	Approved
0.681	Remote Similarity	NPD6881	Approved
0.6786	Remote Similarity	NPD7639	Approved
0.6786	Remote Similarity	NPD7640	Approved
0.6777	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6777	Remote Similarity	NPD7115	Discovery
0.6768	Remote Similarity	NPD6933	Approved
0.6757	Remote Similarity	NPD4755	Approved
0.6752	Remote Similarity	NPD6372	Approved
0.6752	Remote Similarity	NPD6373	Approved
0.6735	Remote Similarity	NPD4784	Approved
0.6735	Remote Similarity	NPD4785	Approved
0.6727	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6724	Remote Similarity	NPD5697	Approved
0.6724	Remote Similarity	NPD5701	Approved
0.6701	Remote Similarity	NPD4243	Approved
0.6698	Remote Similarity	NPD7750	Discontinued
0.6697	Remote Similarity	NPD4202	Approved
0.6697	Remote Similarity	NPD6399	Phase 3
0.6695	Remote Similarity	NPD6883	Approved
0.6695	Remote Similarity	NPD7290	Approved
0.6695	Remote Similarity	NPD7102	Approved
0.6667	Remote Similarity	NPD6931	Approved
0.6667	Remote Similarity	NPD6930	Phase 2
0.6667	Remote Similarity	NPD6686	Approved
0.6667	Remote Similarity	NPD5956	Approved
0.6639	Remote Similarity	NPD6650	Approved
0.6639	Remote Similarity	NPD6869	Approved
0.6639	Remote Similarity	NPD6617	Approved
0.6639	Remote Similarity	NPD8130	Phase 1
0.6639	Remote Similarity	NPD6649	Approved
0.6639	Remote Similarity	NPD6847	Approved
0.6637	Remote Similarity	NPD5286	Approved
0.6637	Remote Similarity	NPD5285	Approved
0.6637	Remote Similarity	NPD4696	Approved
0.6637	Remote Similarity	NPD4700	Approved
0.661	Remote Similarity	NPD6012	Approved
0.661	Remote Similarity	NPD6013	Approved
0.661	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.661	Remote Similarity	NPD6014	Approved
0.6607	Remote Similarity	NPD6084	Phase 2
0.6607	Remote Similarity	NPD6083	Phase 2
0.6587	Remote Similarity	NPD8328	Phase 3
0.6577	Remote Similarity	NPD7991	Discontinued
0.6571	Remote Similarity	NPD4786	Approved
0.6569	Remote Similarity	NPD6929	Approved
0.6566	Remote Similarity	NPD6924	Approved
0.6566	Remote Similarity	NPD6926	Approved
0.656	Remote Similarity	NPD5983	Phase 2
0.6535	Remote Similarity	NPD6932	Approved
0.6525	Remote Similarity	NPD6011	Approved
0.6522	Remote Similarity	NPD5224	Approved
0.6522	Remote Similarity	NPD5211	Phase 2
0.6522	Remote Similarity	NPD5225	Approved
0.6522	Remote Similarity	NPD4633	Approved
0.6522	Remote Similarity	NPD5226	Approved
0.6514	Remote Similarity	NPD3168	Discontinued
0.65	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6495	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.6484	Remote Similarity	NPD6336	Discontinued
0.6466	Remote Similarity	NPD5175	Approved
0.6466	Remote Similarity	NPD5174	Approved
0.6455	Remote Similarity	NPD7087	Discontinued
0.6442	Remote Similarity	NPD6902	Approved
0.6435	Remote Similarity	NPD5223	Approved
0.6422	Remote Similarity	NPD5328	Approved
0.6422	Remote Similarity	NPD6051	Approved
0.6422	Remote Similarity	NPD4753	Phase 2
0.641	Remote Similarity	NPD5141	Approved
0.6408	Remote Similarity	NPD6683	Phase 2
0.6404	Remote Similarity	NPD4225	Approved
0.6381	Remote Similarity	NPD3667	Approved
0.6379	Remote Similarity	NPD7632	Discontinued
0.6373	Remote Similarity	NPD5776	Phase 2
0.6373	Remote Similarity	NPD6925	Approved
0.6356	Remote Similarity	NPD4767	Approved
0.6356	Remote Similarity	NPD4768	Approved
0.6355	Remote Similarity	NPD6893	Approved
0.6346	Remote Similarity	NPD7509	Discontinued
0.6346	Remote Similarity	NPD7514	Phase 3
0.6339	Remote Similarity	NPD6001	Approved
0.6337	Remote Similarity	NPD4190	Phase 3
0.6337	Remote Similarity	NPD5275	Approved
0.6325	Remote Similarity	NPD4754	Approved
0.6312	Remote Similarity	NPD7625	Phase 1
0.6311	Remote Similarity	NPD7145	Approved
0.6311	Remote Similarity	NPD6053	Discontinued
0.6306	Remote Similarity	NPD8034	Phase 2
0.6306	Remote Similarity	NPD6079	Approved
0.6306	Remote Similarity	NPD8035	Phase 2
0.6299	Remote Similarity	NPD8513	Phase 3
0.6299	Remote Similarity	NPD8515	Approved
0.6299	Remote Similarity	NPD8516	Approved
0.6299	Remote Similarity	NPD8517	Approved
0.6296	Remote Similarity	NPD3618	Phase 1
0.6293	Remote Similarity	NPD5344	Discontinued
0.629	Remote Similarity	NPD6274	Approved
0.6283	Remote Similarity	NPD5695	Phase 3
0.6281	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.627	Remote Similarity	NPD7100	Approved
0.627	Remote Similarity	NPD7101	Approved
0.6262	Remote Similarity	NPD3133	Approved
0.6262	Remote Similarity	NPD3666	Approved
0.6262	Remote Similarity	NPD3665	Phase 1
0.6261	Remote Similarity	NPD5696	Approved
0.625	Remote Similarity	NPD4195	Approved
0.625	Remote Similarity	NPD5128	Approved
0.625	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.625	Remote Similarity	NPD4730	Approved
0.625	Remote Similarity	NPD4729	Approved
0.6204	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.62	Remote Similarity	NPD7152	Approved
0.62	Remote Similarity	NPD7151	Approved
0.62	Remote Similarity	NPD7150	Approved
0.6195	Remote Similarity	NPD7748	Approved
0.619	Remote Similarity	NPD6335	Approved
0.619	Remote Similarity	NPD7332	Phase 2
0.6182	Remote Similarity	NPD6903	Approved
0.6182	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6174	Remote Similarity	NPD7902	Approved
0.6172	Remote Similarity	NPD6908	Approved
0.6172	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6172	Remote Similarity	NPD6909	Approved
0.6162	Remote Similarity	NPD6922	Approved
0.6162	Remote Similarity	NPD6923	Approved
0.6161	Remote Similarity	NPD7637	Suspended
0.6161	Remote Similarity	NPD7515	Phase 2
0.6148	Remote Similarity	NPD5251	Approved
0.6148	Remote Similarity	NPD5247	Approved
0.6148	Remote Similarity	NPD5249	Phase 3
0.6148	Remote Similarity	NPD5248	Approved
0.6148	Remote Similarity	NPD5250	Approved
0.6147	Remote Similarity	NPD5330	Approved
0.6147	Remote Similarity	NPD6684	Approved
0.6147	Remote Similarity	NPD7146	Approved
0.6147	Remote Similarity	NPD7521	Approved
0.6147	Remote Similarity	NPD6409	Approved
0.6147	Remote Similarity	NPD7334	Approved
0.614	Remote Similarity	NPD4629	Approved
0.614	Remote Similarity	NPD5210	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