NPASS Compound

Structure

NPC40574 OpenBabel07101719252D 31 34 0 0 1 0 0 0 0 0999 V2000 -3.2999 5.3019 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4589 4.0148 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8136 3.9637 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3884 0.7202 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6942 0.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9726 2.6765 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2294 2.0074 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9021 -0.6180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1590 -1.2872 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6581 1.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3364 1.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5078 4.3238 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7647 3.6547 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.4373 1.0292 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.4641 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6942 0.3601 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.2079 -0.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.7431 0.6691 0.0000 C 0 0 1 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 4.3301 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.5352 -1.6473 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 17 1 0 0 0 0 2 17 1 0 0 0 0 6 27 1 0 0 0 0 7 8 2 0 0 0 0 7 18 1 0 0 0 0 8 19 1 0 0 0 0 9 10 1 0 0 0 0 9 21 1 0 0 0 0 10 25 1 0 0 0 0 11 13 1 0 0 0 0 11 20 1 0 0 0 0 12 14 1 0 0 0 0 12 24 1 0 0 0 0 13 26 1 0 0 0 0 14 27 1 0 0 0 0 15 20 1 0 0 0 0 15 22 1 0 0 0 0 16 23 1 0 0 0 0 17 18 1 0 0 0 0 18 3 1 1 0 0 0 19 4 1 6 0 0 0 19 21 1 0 0 0 0 20 29 2 0 0 0 0 21 27 1 6 0 0 0 22 23 1 0 0 0 0 22 26 1 1 0 0 0 23 30 2 0 0 0 0 24 26 1 6 0 0 0 24 28 1 0 0 0 0 25 28 1 0 0 0 0 25 31 2 0 0 0 0 26 5 1 6 0 0 0 27 28 1 6 0 0 0 28 16 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	426.31
Volume:	474.443
LogP:	4.328
LogD:	4.884
LogS:	-4.828
# Rotatable Bonds:	4
TPSA:	51.21
# H-Bond Aceptor:	3
# H-Bond Donor:	0
# Rings:	4
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.503
Synthetic Accessibility Score:	5.363
Fsp3:	0.821
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:	-5.062
MDCK Permeability:	3.450615986366756e-05
Pgp-inhibitor:	0.762
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.008
20% Bioavailability (F20%):	0.388
30% Bioavailability (F30%):	0.968

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.276
Plasma Protein Binding (PPB):	81.98468780517578%
Volume Distribution (VD):	1.192
Pgp-substrate:	2.0070698261260986%

ADMET: Metabolism

CYP1A2-inhibitor:	0.024
CYP1A2-substrate:	0.722
CYP2C19-inhibitor:	0.167
CYP2C19-substrate:	0.963
CYP2C9-inhibitor:	0.359
CYP2C9-substrate:	0.382
CYP2D6-inhibitor:	0.008
CYP2D6-substrate:	0.688
CYP3A4-inhibitor:	0.789
CYP3A4-substrate:	0.884

ADMET: Excretion

Clearance (CL):	3.626
Half-life (T1/2):	0.714

ADMET: Toxicity

hERG Blockers:	0.005
Human Hepatotoxicity (H-HT):	0.491
Drug-inuced Liver Injury (DILI):	0.199
AMES Toxicity:	0.008
Rat Oral Acute Toxicity:	0.942
Maximum Recommended Daily Dose:	0.36
Skin Sensitization:	0.165
Carcinogencity:	0.008
Eye Corrosion:	0.004
Eye Irritation:	0.041
Respiratory Toxicity:	0.178

Download Data

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

Natural Product: NPC40574

Natural Product ID:	NPC40574
*Common Name:**	Dankasterone B
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	GERUCBMNWOYIOR-NLEPFULASA-N
Standard InCHI:	InChI=1S/C28H42O3/c1-17(2)18(3)7-8-19(4)21-9-10-25(31)28-16-23(30)22-15-20(29)11-13-26(22,5)24(28)12-14-27(21,28)6/h7-8,17-19,21-22,24H,9-16H2,1-6H3/b8-7+/t18-,19+,21+,22-,24+,26-,27+,28-/m0/s1
SMILES:	O=C1CC[C@]2([C@@H](C1)C(=O)C[C@]13[C@@H]2CC[C@]3(C)[C@H](CCC1=O)[C@@H](/C=C/[C@@H](C(C)C)C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL399917
PubChem CID:	24179239
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001550] Sesquiterpenoids

*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
NPO33119	gymnascella dankaliensis	Species	Gymnoascaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17067147]
NPO33119	gymnascella dankaliensis	Species	Gymnoascaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17988094]
NPO33119	gymnascella dankaliensis	Species	Gymnoascaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18284207]
NPO33119	gymnascella dankaliensis	Species	Gymnoascaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25600409]
NPO40805	Calvatia nipponica	Species	n.a.	n.a.	Fruiting Bodies	n.a.	n.a.	PMID[32940037]

☑ 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	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT168	Cell Line	P388	Mus musculus	ED50	=	2.8	ug ml-1	PMID[523522]

☑ 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 NPC40574 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	172
0.1-0.2	2037
0.2-0.3	14174
0.3-0.4	11750
0.4-0.5	7024
0.5-0.6	5188
0.6-0.7	2004
0.7-0.8	294
0.8-0.85	25
0.85-0.9	26
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9254	High Similarity	NPC182815
0.9143	High Similarity	NPC255650
0.9118	High Similarity	NPC214770
0.9118	High Similarity	NPC477856
0.9104	High Similarity	NPC20610
0.9091	High Similarity	NPC323005
0.9	High Similarity	NPC309852
0.8986	High Similarity	NPC115023
0.8986	High Similarity	NPC305501
0.8986	High Similarity	NPC470078
0.8986	High Similarity	NPC234707
0.8889	High Similarity	NPC470557
0.8889	High Similarity	NPC91665
0.8873	High Similarity	NPC293803
0.8857	High Similarity	NPC251705
0.8857	High Similarity	NPC303613
0.8857	High Similarity	NPC474228
0.8841	High Similarity	NPC35734
0.8841	High Similarity	NPC159577
0.8841	High Similarity	NPC282593
0.8841	High Similarity	NPC260040
0.8841	High Similarity	NPC307176
0.875	High Similarity	NPC69408
0.8714	High Similarity	NPC54123
0.8696	High Similarity	NPC139397
0.8592	High Similarity	NPC470044
0.8592	High Similarity	NPC470045
0.8571	High Similarity	NPC2634
0.8571	High Similarity	NPC251929
0.8571	High Similarity	NPC265782
0.8533	High Similarity	NPC474509
0.8529	High Similarity	NPC168824
0.8529	High Similarity	NPC107704
0.8529	High Similarity	NPC189917
0.8529	High Similarity	NPC96812
0.8529	High Similarity	NPC39462
0.8529	High Similarity	NPC43300
0.8514	High Similarity	NPC470052
0.8514	High Similarity	NPC82635
0.8507	High Similarity	NPC469662
0.8472	Intermediate Similarity	NPC474796
0.8472	Intermediate Similarity	NPC474797
0.8472	Intermediate Similarity	NPC255021
0.8472	Intermediate Similarity	NPC329866
0.8429	Intermediate Similarity	NPC477857
0.8429	Intermediate Similarity	NPC286814
0.84	Intermediate Similarity	NPC215843
0.8358	Intermediate Similarity	NPC197238
0.8358	Intermediate Similarity	NPC202118
0.8356	Intermediate Similarity	NPC473171
0.8286	Intermediate Similarity	NPC142754
0.8286	Intermediate Similarity	NPC82477
0.8286	Intermediate Similarity	NPC39157
0.8286	Intermediate Similarity	NPC296697
0.8209	Intermediate Similarity	NPC60565
0.8194	Intermediate Similarity	NPC190035
0.8194	Intermediate Similarity	NPC225467
0.8143	Intermediate Similarity	NPC20181
0.8143	Intermediate Similarity	NPC176107
0.8143	Intermediate Similarity	NPC220210
0.8082	Intermediate Similarity	NPC474488
0.8028	Intermediate Similarity	NPC188292
0.8028	Intermediate Similarity	NPC260474
0.8	Intermediate Similarity	NPC151464
0.8	Intermediate Similarity	NPC469793
0.8	Intermediate Similarity	NPC92327
0.8	Intermediate Similarity	NPC137493
0.8	Intermediate Similarity	NPC143597
0.8	Intermediate Similarity	NPC469796
0.7973	Intermediate Similarity	NPC159497
0.7949	Intermediate Similarity	NPC147066
0.7945	Intermediate Similarity	NPC5701
0.7945	Intermediate Similarity	NPC223187
0.7945	Intermediate Similarity	NPC181204
0.7922	Intermediate Similarity	NPC170793
0.7922	Intermediate Similarity	NPC90965
0.7917	Intermediate Similarity	NPC256846
0.7879	Intermediate Similarity	NPC49575
0.7879	Intermediate Similarity	NPC55004
0.7879	Intermediate Similarity	NPC230823
0.7879	Intermediate Similarity	NPC267626
0.7875	Intermediate Similarity	NPC178025
0.7875	Intermediate Similarity	NPC16287
0.7875	Intermediate Similarity	NPC181743
0.7848	Intermediate Similarity	NPC320514
0.7848	Intermediate Similarity	NPC472239
0.7848	Intermediate Similarity	NPC100297
0.7846	Intermediate Similarity	NPC184819
0.7805	Intermediate Similarity	NPC93778
0.7805	Intermediate Similarity	NPC476293
0.7792	Intermediate Similarity	NPC469996
0.7792	Intermediate Similarity	NPC115515
0.7792	Intermediate Similarity	NPC228911
0.7778	Intermediate Similarity	NPC87141
0.7778	Intermediate Similarity	NPC60350
0.7778	Intermediate Similarity	NPC29447
0.7763	Intermediate Similarity	NPC474463
0.775	Intermediate Similarity	NPC167103
0.775	Intermediate Similarity	NPC470047
0.775	Intermediate Similarity	NPC470046
0.7733	Intermediate Similarity	NPC211641
0.7722	Intermediate Similarity	NPC201912
0.7722	Intermediate Similarity	NPC4166
0.7722	Intermediate Similarity	NPC38350
0.7714	Intermediate Similarity	NPC473902
0.7714	Intermediate Similarity	NPC212210
0.7692	Intermediate Similarity	NPC53245
0.7692	Intermediate Similarity	NPC288296
0.7692	Intermediate Similarity	NPC477371
0.7681	Intermediate Similarity	NPC213152
0.7654	Intermediate Similarity	NPC59453
0.7654	Intermediate Similarity	NPC214043
0.7654	Intermediate Similarity	NPC221758
0.7654	Intermediate Similarity	NPC85774
0.7654	Intermediate Similarity	NPC82902
0.7647	Intermediate Similarity	NPC259261
0.7639	Intermediate Similarity	NPC475523
0.7625	Intermediate Similarity	NPC311092
0.7625	Intermediate Similarity	NPC142253
0.7625	Intermediate Similarity	NPC469805
0.7625	Intermediate Similarity	NPC240302
0.7625	Intermediate Similarity	NPC133391
0.7625	Intermediate Similarity	NPC469804
0.7625	Intermediate Similarity	NPC3511
0.7625	Intermediate Similarity	NPC193347
0.7625	Intermediate Similarity	NPC472867
0.7625	Intermediate Similarity	NPC260956
0.7606	Intermediate Similarity	NPC251118
0.7595	Intermediate Similarity	NPC472478
0.759	Intermediate Similarity	NPC58063
0.7576	Intermediate Similarity	NPC200258
0.7571	Intermediate Similarity	NPC472306
0.7571	Intermediate Similarity	NPC165695
0.7564	Intermediate Similarity	NPC63020
0.7561	Intermediate Similarity	NPC471224
0.7561	Intermediate Similarity	NPC11711
0.7561	Intermediate Similarity	NPC469948
0.7561	Intermediate Similarity	NPC470223
0.7561	Intermediate Similarity	NPC474218
0.7536	Intermediate Similarity	NPC25853
0.7536	Intermediate Similarity	NPC127582
0.7534	Intermediate Similarity	NPC310992
0.7531	Intermediate Similarity	NPC83569
0.7531	Intermediate Similarity	NPC21667
0.7531	Intermediate Similarity	NPC474976
0.7531	Intermediate Similarity	NPC41539
0.7531	Intermediate Similarity	NPC279639
0.7531	Intermediate Similarity	NPC474790
0.7531	Intermediate Similarity	NPC69279
0.7531	Intermediate Similarity	NPC3856
0.7531	Intermediate Similarity	NPC477852
0.75	Intermediate Similarity	NPC477372
0.75	Intermediate Similarity	NPC266295
0.75	Intermediate Similarity	NPC30215
0.75	Intermediate Similarity	NPC219232
0.75	Intermediate Similarity	NPC193360
0.75	Intermediate Similarity	NPC94991
0.75	Intermediate Similarity	NPC176171
0.75	Intermediate Similarity	NPC128346
0.747	Intermediate Similarity	NPC469994
0.747	Intermediate Similarity	NPC475022
0.747	Intermediate Similarity	NPC470051
0.747	Intermediate Similarity	NPC222613
0.747	Intermediate Similarity	NPC474778
0.747	Intermediate Similarity	NPC264127
0.747	Intermediate Similarity	NPC145879
0.747	Intermediate Similarity	NPC474733
0.747	Intermediate Similarity	NPC31564
0.747	Intermediate Similarity	NPC470050
0.747	Intermediate Similarity	NPC118648
0.747	Intermediate Similarity	NPC51014
0.747	Intermediate Similarity	NPC474732
0.7468	Intermediate Similarity	NPC158846
0.7468	Intermediate Similarity	NPC201459
0.7468	Intermediate Similarity	NPC190211
0.7468	Intermediate Similarity	NPC192744
0.7465	Intermediate Similarity	NPC285371
0.7465	Intermediate Similarity	NPC475124
0.7463	Intermediate Similarity	NPC474105
0.7442	Intermediate Similarity	NPC272746
0.7439	Intermediate Similarity	NPC87552
0.7439	Intermediate Similarity	NPC144258
0.7439	Intermediate Similarity	NPC237712
0.7439	Intermediate Similarity	NPC473246
0.7436	Intermediate Similarity	NPC66105
0.7429	Intermediate Similarity	NPC475795
0.7412	Intermediate Similarity	NPC285982
0.7412	Intermediate Similarity	NPC262043
0.7412	Intermediate Similarity	NPC2983
0.7407	Intermediate Similarity	NPC328351
0.7407	Intermediate Similarity	NPC327969
0.7407	Intermediate Similarity	NPC469806
0.7407	Intermediate Similarity	NPC469799
0.7407	Intermediate Similarity	NPC151519
0.7407	Intermediate Similarity	NPC321289
0.7403	Intermediate Similarity	NPC201027
0.7391	Intermediate Similarity	NPC472304
0.7391	Intermediate Similarity	NPC276764
0.7381	Intermediate Similarity	NPC475740
0.7381	Intermediate Similarity	NPC317590

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 NPC40574 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	161
0.1-0.2	2104
0.2-0.3	4728
0.3-0.4	1483
0.4-0.5	333
0.5-0.6	133
0.6-0.7	159
0.7-0.8	42
0.8-0.85	4
0.85-0.9	3
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8841	High Similarity	NPD4747	Approved
0.8696	High Similarity	NPD4137	Phase 3
0.8571	High Similarity	NPD4691	Approved
0.8551	High Similarity	NPD3621	Clinical (unspecified phase)
0.8472	Intermediate Similarity	NPD4687	Approved
0.8472	Intermediate Similarity	NPD5733	Approved
0.8472	Intermediate Similarity	NPD4058	Approved
0.8194	Intermediate Similarity	NPD5276	Approved
0.7654	Intermediate Similarity	NPD4786	Approved
0.7625	Intermediate Similarity	NPD4223	Phase 3
0.7625	Intermediate Similarity	NPD4221	Approved
0.7561	Intermediate Similarity	NPD5329	Approved
0.747	Intermediate Similarity	NPD6098	Approved
0.7439	Intermediate Similarity	NPD4197	Approved
0.7407	Intermediate Similarity	NPD3667	Approved
0.7317	Intermediate Similarity	NPD3527	Clinical (unspecified phase)
0.7294	Intermediate Similarity	NPD6672	Approved
0.7294	Intermediate Similarity	NPD5737	Approved
0.7294	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7262	Intermediate Similarity	NPD6409	Approved
0.7262	Intermediate Similarity	NPD4688	Approved
0.7262	Intermediate Similarity	NPD5205	Approved
0.7262	Intermediate Similarity	NPD7521	Approved
0.7262	Intermediate Similarity	NPD6684	Approved
0.7262	Intermediate Similarity	NPD4693	Phase 3
0.7262	Intermediate Similarity	NPD5690	Phase 2
0.7262	Intermediate Similarity	NPD4690	Approved
0.7262	Intermediate Similarity	NPD5330	Approved
0.7262	Intermediate Similarity	NPD7334	Approved
0.7262	Intermediate Similarity	NPD4138	Approved
0.7262	Intermediate Similarity	NPD4689	Approved
0.7262	Intermediate Similarity	NPD7146	Approved
0.7241	Intermediate Similarity	NPD6079	Approved
0.7229	Intermediate Similarity	NPD3665	Phase 1
0.7229	Intermediate Similarity	NPD3668	Phase 3
0.7229	Intermediate Similarity	NPD3666	Approved
0.7229	Intermediate Similarity	NPD3133	Approved
0.7209	Intermediate Similarity	NPD6904	Approved
0.7209	Intermediate Similarity	NPD6673	Approved
0.7209	Intermediate Similarity	NPD6080	Approved
0.7209	Intermediate Similarity	NPD5328	Approved
0.7159	Intermediate Similarity	NPD6399	Phase 3
0.7125	Intermediate Similarity	NPD3617	Approved
0.7108	Intermediate Similarity	NPD4788	Approved
0.7093	Intermediate Similarity	NPD5208	Approved
0.7093	Intermediate Similarity	NPD6903	Approved
0.7073	Intermediate Similarity	NPD8028	Phase 2
0.7059	Intermediate Similarity	NPD3618	Phase 1
0.7059	Intermediate Similarity	NPD4694	Approved
0.7059	Intermediate Similarity	NPD5280	Approved
0.7037	Intermediate Similarity	NPD4195	Approved
0.7011	Intermediate Similarity	NPD4753	Phase 2
0.6932	Remote Similarity	NPD5207	Approved
0.6889	Remote Similarity	NPD5769	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD4139	Approved
0.6867	Remote Similarity	NPD4692	Approved
0.686	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.686	Remote Similarity	NPD4623	Approved
0.686	Remote Similarity	NPD4519	Discontinued
0.686	Remote Similarity	NPD5279	Phase 3
0.6854	Remote Similarity	NPD5284	Approved
0.6854	Remote Similarity	NPD5694	Approved
0.6854	Remote Similarity	NPD5693	Phase 1
0.6854	Remote Similarity	NPD6050	Approved
0.6854	Remote Similarity	NPD5281	Approved
0.6842	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD5360	Phase 3
0.6835	Remote Similarity	NPD4785	Approved
0.6835	Remote Similarity	NPD4784	Approved
0.6813	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6813	Remote Similarity	NPD5210	Approved
0.6813	Remote Similarity	NPD4629	Approved
0.6795	Remote Similarity	NPD4243	Approved
0.6778	Remote Similarity	NPD4202	Approved
0.6761	Remote Similarity	NPD287	Approved
0.6747	Remote Similarity	NPD4695	Discontinued
0.6744	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6742	Remote Similarity	NPD5692	Phase 3
0.6739	Remote Similarity	NPD5222	Approved
0.6739	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6739	Remote Similarity	NPD5221	Approved
0.6739	Remote Similarity	NPD4697	Phase 3
0.6707	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6703	Remote Similarity	NPD6001	Approved
0.6667	Remote Similarity	NPD4789	Approved
0.6667	Remote Similarity	NPD6084	Phase 2
0.6667	Remote Similarity	NPD6083	Phase 2
0.6667	Remote Similarity	NPD5173	Approved
0.6591	Remote Similarity	NPD3573	Approved
0.6582	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6582	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6582	Remote Similarity	NPD6081	Approved
0.6579	Remote Similarity	NPD4224	Phase 2
0.6556	Remote Similarity	NPD4096	Approved
0.6548	Remote Similarity	NPD7525	Registered
0.6543	Remote Similarity	NPD7339	Approved
0.6543	Remote Similarity	NPD6942	Approved
0.6526	Remote Similarity	NPD4696	Approved
0.6526	Remote Similarity	NPD5285	Approved
0.6526	Remote Similarity	NPD5286	Approved
0.6522	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD7900	Approved
0.6517	Remote Similarity	NPD4518	Approved
0.6489	Remote Similarity	NPD4755	Approved
0.6484	Remote Similarity	NPD7515	Phase 2
0.6484	Remote Similarity	NPD8034	Phase 2
0.6484	Remote Similarity	NPD8035	Phase 2
0.6458	Remote Similarity	NPD5223	Approved
0.6456	Remote Similarity	NPD7143	Approved
0.6456	Remote Similarity	NPD7144	Approved
0.6456	Remote Similarity	NPD4245	Approved
0.6456	Remote Similarity	NPD4244	Approved
0.6452	Remote Similarity	NPD5695	Phase 3
0.6447	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.6444	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6421	Remote Similarity	NPD5696	Approved
0.6413	Remote Similarity	NPD5133	Approved
0.6392	Remote Similarity	NPD5226	Approved
0.6392	Remote Similarity	NPD5225	Approved
0.6392	Remote Similarity	NPD4633	Approved
0.6392	Remote Similarity	NPD5211	Phase 2
0.6392	Remote Similarity	NPD5224	Approved
0.6392	Remote Similarity	NPD5091	Approved
0.6375	Remote Similarity	NPD7150	Approved
0.6375	Remote Similarity	NPD4758	Discontinued
0.6375	Remote Similarity	NPD5777	Approved
0.6375	Remote Similarity	NPD7152	Approved
0.6375	Remote Similarity	NPD7151	Approved
0.6354	Remote Similarity	NPD4700	Approved
0.6344	Remote Similarity	NPD7748	Approved
0.6341	Remote Similarity	NPD4190	Phase 3
0.6341	Remote Similarity	NPD5275	Approved
0.6329	Remote Similarity	NPD3698	Phase 2
0.6329	Remote Similarity	NPD6923	Approved
0.6329	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6329	Remote Similarity	NPD6922	Approved
0.6329	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6327	Remote Similarity	NPD5175	Approved
0.6327	Remote Similarity	NPD6052	Approved
0.6327	Remote Similarity	NPD5174	Approved
0.6316	Remote Similarity	NPD7902	Approved
0.63	Remote Similarity	NPD6614	Approved
0.6277	Remote Similarity	NPD5654	Approved
0.6265	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6263	Remote Similarity	NPD5141	Approved
0.625	Remote Similarity	NPD6938	Clinical (unspecified phase)
0.625	Remote Similarity	NPD6939	Phase 2
0.6238	Remote Similarity	NPD6881	Approved
0.6238	Remote Similarity	NPD6899	Approved
0.622	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.622	Remote Similarity	NPD6926	Approved
0.622	Remote Similarity	NPD6924	Approved
0.6214	Remote Similarity	NPD6649	Approved
0.6214	Remote Similarity	NPD6650	Approved
0.6207	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.62	Remote Similarity	NPD5739	Approved
0.62	Remote Similarity	NPD6402	Approved
0.62	Remote Similarity	NPD7128	Approved
0.62	Remote Similarity	NPD6675	Approved
0.619	Remote Similarity	NPD6932	Approved
0.6176	Remote Similarity	NPD6373	Approved
0.6176	Remote Similarity	NPD6372	Approved
0.6162	Remote Similarity	NPD4754	Approved
0.6146	Remote Similarity	NPD5959	Approved
0.6139	Remote Similarity	NPD5697	Approved
0.6119	Remote Similarity	NPD345	Approved
0.6119	Remote Similarity	NPD344	Approved
0.6119	Remote Similarity	NPD343	Approved
0.6118	Remote Similarity	NPD5364	Discontinued
0.6118	Remote Similarity	NPD7145	Approved
0.6117	Remote Similarity	NPD7290	Approved
0.6117	Remote Similarity	NPD6883	Approved
0.6117	Remote Similarity	NPD7102	Approved
0.6087	Remote Similarity	NPD6051	Approved
0.6082	Remote Similarity	NPD7638	Approved
0.6078	Remote Similarity	NPD4730	Approved
0.6078	Remote Similarity	NPD7320	Approved
0.6078	Remote Similarity	NPD6011	Approved
0.6078	Remote Similarity	NPD5168	Approved
0.6078	Remote Similarity	NPD4729	Approved
0.6071	Remote Similarity	NPD6933	Approved
0.6071	Remote Similarity	NPD6117	Approved
0.6058	Remote Similarity	NPD6617	Approved
0.6058	Remote Similarity	NPD6869	Approved
0.6058	Remote Similarity	NPD6847	Approved
0.6058	Remote Similarity	NPD8130	Phase 1
0.6042	Remote Similarity	NPD7614	Phase 1
0.6042	Remote Similarity	NPD7732	Phase 3
0.604	Remote Similarity	NPD6008	Approved
0.604	Remote Similarity	NPD4767	Approved
0.604	Remote Similarity	NPD4768	Approved
0.602	Remote Similarity	NPD7639	Approved
0.602	Remote Similarity	NPD6404	Discontinued
0.602	Remote Similarity	NPD7640	Approved
0.6019	Remote Similarity	NPD6012	Approved
0.6019	Remote Similarity	NPD6014	Approved
0.6019	Remote Similarity	NPD6013	Approved
0.6	Remote Similarity	NPD6882	Approved
0.6	Remote Similarity	NPD5776	Phase 2
0.6	Remote Similarity	NPD6925	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