NPASS Compound

Structure

NPC470052 OpenBabel07101718322D 33 36 0 0 1 0 0 0 0 0999 V2000 -2.2382 -2.4680 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9792 -6.0914 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2361 -5.4223 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9641 2.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9641 2.8660 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 0.4067 -1.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4067 0.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4743 -6.2722 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9000 -3.9543 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5909 -3.0032 0.0000 C 0 0 0 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 1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5388 -0.5000 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 4.3301 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8781 -4.1622 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 -0.9511 0.3090 0.0000 C 0 0 0 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 -1.2601 -2.2601 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.9511 -1.3090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 4.3301 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1871 -5.1132 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.1962 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.1653 -5.3212 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 27 1 0 0 0 0 3 27 1 0 0 0 0 4 28 1 0 0 0 0 5 28 1 0 0 0 0 7 30 1 0 0 0 0 9 33 1 0 0 0 0 10 11 1 0 0 0 0 10 17 2 0 0 0 0 11 21 1 0 0 0 0 12 13 1 0 0 0 0 12 24 2 0 0 0 0 13 25 1 0 0 0 0 14 19 1 0 0 0 0 14 22 1 0 0 0 0 15 20 1 0 0 0 0 15 23 1 0 0 0 0 16 18 1 0 0 0 0 16 26 1 0 0 0 0 17 27 1 0 0 0 0 18 29 1 0 0 0 0 19 31 1 0 0 0 0 20 30 1 0 0 0 0 21 1 1 6 0 0 0 21 22 1 0 0 0 0 22 30 1 6 0 0 0 23 24 1 0 0 0 0 23 29 1 1 0 0 0 24 31 1 0 0 0 0 25 28 1 0 0 0 0 25 29 1 0 0 0 0 26 28 1 0 0 0 0 26 32 2 0 0 0 0 27 33 1 0 0 0 0 29 6 1 1 0 0 0 30 31 1 6 0 0 0 31 8 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	454.38
Volume:	520.177
LogP:	7.251
LogD:	5.351
LogS:	-5.935
# Rotatable Bonds:	5
TPSA:	26.3
# H-Bond Aceptor:	2
# H-Bond Donor:	0
# Rings:	4
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.392
Synthetic Accessibility Score:	4.853
Fsp3:	0.839
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.796
MDCK Permeability:	1.0058129191747867e-05
Pgp-inhibitor:	0.927
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.024
20% Bioavailability (F20%):	0.527
30% Bioavailability (F30%):	0.865

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.348
Plasma Protein Binding (PPB):	98.57219696044922%
Volume Distribution (VD):	1.283
Pgp-substrate:	2.360551595687866%

ADMET: Metabolism

CYP1A2-inhibitor:	0.059
CYP1A2-substrate:	0.541
CYP2C19-inhibitor:	0.203
CYP2C19-substrate:	0.959
CYP2C9-inhibitor:	0.339
CYP2C9-substrate:	0.447
CYP2D6-inhibitor:	0.458
CYP2D6-substrate:	0.27
CYP3A4-inhibitor:	0.917
CYP3A4-substrate:	0.85

ADMET: Excretion

Clearance (CL):	5.864
Half-life (T1/2):	0.05

ADMET: Toxicity

hERG Blockers:	0.057
Human Hepatotoxicity (H-HT):	0.417
Drug-inuced Liver Injury (DILI):	0.034
AMES Toxicity:	0.002
Rat Oral Acute Toxicity:	0.261
Maximum Recommended Daily Dose:	0.912
Skin Sensitization:	0.284
Carcinogencity:	0.511
Eye Corrosion:	0.019
Eye Irritation:	0.024
Respiratory Toxicity:	0.984

Download Data

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

Natural Product: NPC470052

Natural Product ID:	NPC470052
*Common Name:**	(-)-Leucophyllone
IUPAC Name:	(9R,10R,13S,14S,17S)-17-[(E,2S)-6-methoxy-6-methylhept-4-en-2-yl]-4,4,10,13,14-pentamethyl-1,2,5,6,9,11,12,15,16,17-decahydrocyclopenta[a]phenanthren-3-one
Synonyms:	(-)-Leucophyllone
Standard InCHIKey:	VUTMJNYAUWPTQA-ZLEOEWCPSA-N
Standard InCHI:	InChI=1S/C31H50O2/c1-21(11-10-17-27(2,3)33-9)22-14-19-31(8)24-12-13-25-28(4,5)26(32)16-18-29(25,6)23(24)15-20-30(22,31)7/h10,12,17,21-23,25H,11,13-16,18-20H2,1-9H3/b17-10+/t21-,22-,23-,25?,29+,30-,31+/m0/s1
SMILES:	CC(CC=CC(C)(C)OC)C1CCC2(C1(CCC3C2=CCC4C3(CCC(=O)C4(C)C)C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1668107
PubChem CID:	15241162
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids

*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
NPO19594	Cornus walteri	Species	Cornaceae	Eukaryota	n.a.	stem	n.a.	PMID[21182258]
NPO19594	Cornus walteri	Species	Cornaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21182258]
NPO19594	Cornus walteri	Species	Cornaceae	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	4

Activity Type	# Activity
Cell Line	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	IC50	=	24860.0	nM	PMID[492304]
NPT146	Cell Line	SK-OV-3	Homo sapiens	IC50	=	18040.0	nM	PMID[492304]
NPT147	Cell Line	SK-MEL-2	Homo sapiens	IC50	=	21170.0	nM	PMID[492304]
NPT574	Cell Line	XF498	Homo sapiens	IC50	=	18210.0	nM	PMID[492304]

☑ 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 NPC470052 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	1515
0.2-0.3	7034
0.3-0.4	16436
0.4-0.5	7538
0.5-0.6	6705
0.6-0.7	2784
0.7-0.8	457
0.8-0.85	34
0.85-0.9	20
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9589	High Similarity	NPC470557
0.8889	High Similarity	NPC182815
0.8861	High Similarity	NPC470047
0.8861	High Similarity	NPC470046
0.8816	High Similarity	NPC91665
0.875	High Similarity	NPC20610
0.8649	High Similarity	NPC470078
0.8649	High Similarity	NPC115023
0.859	High Similarity	NPC190211
0.8537	High Similarity	NPC470051
0.8537	High Similarity	NPC470050
0.8533	High Similarity	NPC474228
0.8533	High Similarity	NPC303613
0.8533	High Similarity	NPC251705
0.8514	High Similarity	NPC35734
0.8514	High Similarity	NPC159577
0.8514	High Similarity	NPC282593
0.8514	High Similarity	NPC307176
0.8514	High Similarity	NPC40574
0.8472	Intermediate Similarity	NPC323005
0.8462	Intermediate Similarity	NPC82635
0.8462	Intermediate Similarity	NPC105197
0.8442	Intermediate Similarity	NPC69408
0.8421	Intermediate Similarity	NPC309852
0.8415	Intermediate Similarity	NPC137493
0.8415	Intermediate Similarity	NPC470048
0.84	Intermediate Similarity	NPC54123
0.84	Intermediate Similarity	NPC305501
0.84	Intermediate Similarity	NPC234707
0.8395	Intermediate Similarity	NPC474976
0.8395	Intermediate Similarity	NPC474790
0.8378	Intermediate Similarity	NPC139397
0.8312	Intermediate Similarity	NPC65650
0.8312	Intermediate Similarity	NPC293803
0.8289	Intermediate Similarity	NPC470045
0.8289	Intermediate Similarity	NPC470044
0.8267	Intermediate Similarity	NPC2634
0.8267	Intermediate Similarity	NPC265782
0.8267	Intermediate Similarity	NPC477856
0.8267	Intermediate Similarity	NPC251929
0.8267	Intermediate Similarity	NPC214770
0.8267	Intermediate Similarity	NPC260040
0.825	Intermediate Similarity	NPC474509
0.8194	Intermediate Similarity	NPC469662
0.8182	Intermediate Similarity	NPC255021
0.8148	Intermediate Similarity	NPC4166
0.8077	Intermediate Similarity	NPC473171
0.8077	Intermediate Similarity	NPC255650
0.8056	Intermediate Similarity	NPC202118
0.8056	Intermediate Similarity	NPC197238
0.8049	Intermediate Similarity	NPC311092
0.8049	Intermediate Similarity	NPC472239
0.8023	Intermediate Similarity	NPC474844
0.8023	Intermediate Similarity	NPC2983
0.8	Intermediate Similarity	NPC163016
0.8	Intermediate Similarity	NPC151488
0.8	Intermediate Similarity	NPC469996
0.8	Intermediate Similarity	NPC75315
0.7976	Intermediate Similarity	NPC471224
0.7975	Intermediate Similarity	NPC474463
0.7952	Intermediate Similarity	NPC41539
0.7949	Intermediate Similarity	NPC329866
0.7949	Intermediate Similarity	NPC20025
0.7949	Intermediate Similarity	NPC474797
0.7949	Intermediate Similarity	NPC474796
0.7931	Intermediate Similarity	NPC320026
0.7901	Intermediate Similarity	NPC215843
0.7901	Intermediate Similarity	NPC170793
0.7901	Intermediate Similarity	NPC90965
0.7895	Intermediate Similarity	NPC286814
0.7882	Intermediate Similarity	NPC472863
0.7867	Intermediate Similarity	NPC176107
0.7841	Intermediate Similarity	NPC190442
0.7841	Intermediate Similarity	NPC475806
0.7831	Intermediate Similarity	NPC142253
0.7831	Intermediate Similarity	NPC100297
0.7831	Intermediate Similarity	NPC268122
0.7831	Intermediate Similarity	NPC3511
0.7831	Intermediate Similarity	NPC472867
0.7816	Intermediate Similarity	NPC285982
0.7802	Intermediate Similarity	NPC291634
0.7802	Intermediate Similarity	NPC126815
0.7791	Intermediate Similarity	NPC128644
0.7765	Intermediate Similarity	NPC472940
0.7765	Intermediate Similarity	NPC470223
0.7765	Intermediate Similarity	NPC472931
0.7765	Intermediate Similarity	NPC474083
0.7763	Intermediate Similarity	NPC82477
0.7763	Intermediate Similarity	NPC296697
0.7763	Intermediate Similarity	NPC142754
0.7763	Intermediate Similarity	NPC188292
0.7763	Intermediate Similarity	NPC260474
0.7763	Intermediate Similarity	NPC39157
0.7753	Intermediate Similarity	NPC229976
0.775	Intermediate Similarity	NPC469796
0.775	Intermediate Similarity	NPC469793
0.7738	Intermediate Similarity	NPC118423
0.7733	Intermediate Similarity	NPC168824
0.7733	Intermediate Similarity	NPC39462
0.7733	Intermediate Similarity	NPC92327
0.7733	Intermediate Similarity	NPC43300
0.7733	Intermediate Similarity	NPC107704
0.7733	Intermediate Similarity	NPC189917
0.7733	Intermediate Similarity	NPC96812
0.7711	Intermediate Similarity	NPC147066
0.7692	Intermediate Similarity	NPC322063
0.7692	Intermediate Similarity	NPC223187
0.7692	Intermediate Similarity	NPC190035
0.7692	Intermediate Similarity	NPC181204
0.7692	Intermediate Similarity	NPC5701
0.7692	Intermediate Similarity	NPC160056
0.7692	Intermediate Similarity	NPC78473
0.7674	Intermediate Similarity	NPC264127
0.7674	Intermediate Similarity	NPC469994
0.7671	Intermediate Similarity	NPC60565
0.7667	Intermediate Similarity	NPC8993
0.7662	Intermediate Similarity	NPC256846
0.7662	Intermediate Similarity	NPC477857
0.7647	Intermediate Similarity	NPC87552
0.7647	Intermediate Similarity	NPC59453
0.7647	Intermediate Similarity	NPC214043
0.7647	Intermediate Similarity	NPC221758
0.7647	Intermediate Similarity	NPC181743
0.7647	Intermediate Similarity	NPC82902
0.7647	Intermediate Similarity	NPC16287
0.7647	Intermediate Similarity	NPC178025
0.7647	Intermediate Similarity	NPC85774
0.7632	Intermediate Similarity	NPC220210
0.7632	Intermediate Similarity	NPC20181
0.7619	Intermediate Similarity	NPC193347
0.7619	Intermediate Similarity	NPC327969
0.7619	Intermediate Similarity	NPC240302
0.7619	Intermediate Similarity	NPC320514
0.7619	Intermediate Similarity	NPC321289
0.7619	Intermediate Similarity	NPC469804
0.7619	Intermediate Similarity	NPC469805
0.7619	Intermediate Similarity	NPC94200
0.7614	Intermediate Similarity	NPC473999
0.7614	Intermediate Similarity	NPC309603
0.7614	Intermediate Similarity	NPC262043
0.7614	Intermediate Similarity	NPC177141
0.7609	Intermediate Similarity	NPC57416
0.7609	Intermediate Similarity	NPC107243
0.7595	Intermediate Similarity	NPC474488
0.759	Intermediate Similarity	NPC472478
0.7586	Intermediate Similarity	NPC136948
0.7586	Intermediate Similarity	NPC90652
0.7586	Intermediate Similarity	NPC476293
0.7586	Intermediate Similarity	NPC93778
0.7586	Intermediate Similarity	NPC58063
0.7586	Intermediate Similarity	NPC317590
0.7582	Intermediate Similarity	NPC33473
0.7582	Intermediate Similarity	NPC171395
0.7558	Intermediate Similarity	NPC269638
0.7558	Intermediate Similarity	NPC60350
0.7558	Intermediate Similarity	NPC474218
0.7558	Intermediate Similarity	NPC8571
0.7558	Intermediate Similarity	NPC469948
0.7558	Intermediate Similarity	NPC29447
0.7556	Intermediate Similarity	NPC474736
0.7553	Intermediate Similarity	NPC310981
0.7532	Intermediate Similarity	NPC87141
0.7529	Intermediate Similarity	NPC279639
0.7529	Intermediate Similarity	NPC3856
0.7528	Intermediate Similarity	NPC76286
0.7528	Intermediate Similarity	NPC48010
0.7528	Intermediate Similarity	NPC273199
0.75	Intermediate Similarity	NPC97884
0.75	Intermediate Similarity	NPC28227
0.75	Intermediate Similarity	NPC166797
0.75	Intermediate Similarity	NPC159497
0.75	Intermediate Similarity	NPC470417
0.75	Intermediate Similarity	NPC201912
0.75	Intermediate Similarity	NPC472220
0.75	Intermediate Similarity	NPC38350
0.7474	Intermediate Similarity	NPC185530
0.7473	Intermediate Similarity	NPC292793
0.7471	Intermediate Similarity	NPC118648
0.7471	Intermediate Similarity	NPC51014
0.7471	Intermediate Similarity	NPC474733
0.7471	Intermediate Similarity	NPC474732
0.7471	Intermediate Similarity	NPC31564
0.7471	Intermediate Similarity	NPC473168
0.7471	Intermediate Similarity	NPC195640
0.7471	Intermediate Similarity	NPC474778
0.7471	Intermediate Similarity	NPC168248
0.7471	Intermediate Similarity	NPC222613
0.7471	Intermediate Similarity	NPC475022
0.7471	Intermediate Similarity	NPC145879
0.747	Intermediate Similarity	NPC477371
0.7468	Intermediate Similarity	NPC225467
0.7467	Intermediate Similarity	NPC212210
0.7444	Intermediate Similarity	NPC473998
0.7444	Intermediate Similarity	NPC262870
0.7444	Intermediate Similarity	NPC218301
0.7442	Intermediate Similarity	NPC144258
0.7442	Intermediate Similarity	NPC320801
0.7442	Intermediate Similarity	NPC473246
0.7442	Intermediate Similarity	NPC470077
0.7442	Intermediate Similarity	NPC237712

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 NPC470052 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	151
0.1-0.2	1513
0.2-0.3	4582
0.3-0.4	2097
0.4-0.5	409
0.5-0.6	173
0.6-0.7	164
0.7-0.8	55
0.8-0.85	4
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8514	High Similarity	NPD4747	Approved
0.8378	Intermediate Similarity	NPD4137	Phase 3
0.8267	Intermediate Similarity	NPD4691	Approved
0.8243	Intermediate Similarity	NPD3621	Clinical (unspecified phase)
0.8182	Intermediate Similarity	NPD4058	Approved
0.8182	Intermediate Similarity	NPD4687	Approved
0.8182	Intermediate Similarity	NPD5733	Approved
0.7922	Intermediate Similarity	NPD5276	Approved
0.7674	Intermediate Similarity	NPD6098	Approved
0.7647	Intermediate Similarity	NPD4786	Approved
0.764	Intermediate Similarity	NPD5693	Phase 1
0.7619	Intermediate Similarity	NPD4221	Approved
0.7619	Intermediate Similarity	NPD4223	Phase 3
0.7558	Intermediate Similarity	NPD5329	Approved
0.75	Intermediate Similarity	NPD5737	Approved
0.75	Intermediate Similarity	NPD6672	Approved
0.7471	Intermediate Similarity	NPD6684	Approved
0.7471	Intermediate Similarity	NPD7521	Approved
0.7471	Intermediate Similarity	NPD7334	Approved
0.7471	Intermediate Similarity	NPD5330	Approved
0.7471	Intermediate Similarity	NPD7146	Approved
0.7471	Intermediate Similarity	NPD6409	Approved
0.7442	Intermediate Similarity	NPD4197	Approved
0.7416	Intermediate Similarity	NPD6080	Approved
0.7416	Intermediate Similarity	NPD6904	Approved
0.7416	Intermediate Similarity	NPD6673	Approved
0.7412	Intermediate Similarity	NPD3667	Approved
0.7303	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD6903	Approved
0.7303	Intermediate Similarity	NPD5208	Approved
0.7273	Intermediate Similarity	NPD4693	Phase 3
0.7273	Intermediate Similarity	NPD5205	Approved
0.7273	Intermediate Similarity	NPD4138	Approved
0.7273	Intermediate Similarity	NPD4519	Discontinued
0.7273	Intermediate Similarity	NPD4688	Approved
0.7273	Intermediate Similarity	NPD4690	Approved
0.7273	Intermediate Similarity	NPD5690	Phase 2
0.7273	Intermediate Similarity	NPD4689	Approved
0.7273	Intermediate Similarity	NPD4623	Approved
0.7253	Intermediate Similarity	NPD6079	Approved
0.7241	Intermediate Similarity	NPD3668	Phase 3
0.7241	Intermediate Similarity	NPD3666	Approved
0.7241	Intermediate Similarity	NPD3665	Phase 1
0.7241	Intermediate Similarity	NPD3133	Approved
0.7222	Intermediate Similarity	NPD4753	Phase 2
0.7222	Intermediate Similarity	NPD6051	Approved
0.7222	Intermediate Similarity	NPD5328	Approved
0.7204	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7174	Intermediate Similarity	NPD6399	Phase 3
0.7143	Intermediate Similarity	NPD5207	Approved
0.7126	Intermediate Similarity	NPD3527	Clinical (unspecified phase)
0.7079	Intermediate Similarity	NPD5280	Approved
0.7079	Intermediate Similarity	NPD3618	Phase 1
0.7079	Intermediate Similarity	NPD4694	Approved
0.7065	Intermediate Similarity	NPD5694	Approved
0.7065	Intermediate Similarity	NPD6050	Approved
0.7059	Intermediate Similarity	NPD4195	Approved
0.7053	Intermediate Similarity	NPD6083	Phase 2
0.7053	Intermediate Similarity	NPD6084	Phase 2
0.7021	Intermediate Similarity	NPD4629	Approved
0.7021	Intermediate Similarity	NPD5210	Approved
0.7011	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.6989	Remote Similarity	NPD4202	Approved
0.6957	Remote Similarity	NPD5692	Phase 3
0.6941	Remote Similarity	NPD3617	Approved
0.6932	Remote Similarity	NPD4788	Approved
0.6915	Remote Similarity	NPD6001	Approved
0.6897	Remote Similarity	NPD4692	Approved
0.6897	Remote Similarity	NPD4139	Approved
0.6889	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6889	Remote Similarity	NPD5279	Phase 3
0.6882	Remote Similarity	NPD5281	Approved
0.6882	Remote Similarity	NPD5284	Approved
0.6867	Remote Similarity	NPD4784	Approved
0.6867	Remote Similarity	NPD4785	Approved
0.6842	Remote Similarity	NPD5695	Phase 3
0.6829	Remote Similarity	NPD4243	Approved
0.6813	Remote Similarity	NPD3573	Approved
0.6804	Remote Similarity	NPD5696	Approved
0.6786	Remote Similarity	NPD8039	Approved
0.6778	Remote Similarity	NPD1694	Approved
0.6771	Remote Similarity	NPD5222	Approved
0.6771	Remote Similarity	NPD5221	Approved
0.6771	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6768	Remote Similarity	NPD5211	Phase 2
0.6744	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6737	Remote Similarity	NPD5769	Clinical (unspecified phase)
0.6735	Remote Similarity	NPD5285	Approved
0.6735	Remote Similarity	NPD5286	Approved
0.6735	Remote Similarity	NPD4696	Approved
0.6729	Remote Similarity	NPD7115	Discovery
0.6705	Remote Similarity	NPD8028	Phase 2
0.6701	Remote Similarity	NPD4755	Approved
0.6701	Remote Similarity	NPD5173	Approved
0.6667	Remote Similarity	NPD5223	Approved
0.6634	Remote Similarity	NPD5141	Approved
0.6633	Remote Similarity	NPD7638	Approved
0.6602	Remote Similarity	NPD6899	Approved
0.6602	Remote Similarity	NPD6881	Approved
0.66	Remote Similarity	NPD5225	Approved
0.66	Remote Similarity	NPD5226	Approved
0.66	Remote Similarity	NPD5224	Approved
0.66	Remote Similarity	NPD4633	Approved
0.6598	Remote Similarity	NPD4697	Phase 3
0.6596	Remote Similarity	NPD4096	Approved
0.6591	Remote Similarity	NPD4695	Discontinued
0.6588	Remote Similarity	NPD6942	Approved
0.6588	Remote Similarity	NPD7339	Approved
0.6582	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.6579	Remote Similarity	NPD287	Approved
0.6569	Remote Similarity	NPD5739	Approved
0.6569	Remote Similarity	NPD6675	Approved
0.6569	Remote Similarity	NPD6402	Approved
0.6569	Remote Similarity	NPD7128	Approved
0.6566	Remote Similarity	NPD7640	Approved
0.6566	Remote Similarity	NPD7639	Approved
0.6566	Remote Similarity	NPD4700	Approved
0.6559	Remote Similarity	NPD4518	Approved
0.6535	Remote Similarity	NPD6052	Approved
0.6535	Remote Similarity	NPD5174	Approved
0.6535	Remote Similarity	NPD5175	Approved
0.6505	Remote Similarity	NPD6614	Approved
0.6505	Remote Similarity	NPD5697	Approved
0.6495	Remote Similarity	NPD5654	Approved
0.6476	Remote Similarity	NPD7290	Approved
0.6476	Remote Similarity	NPD7102	Approved
0.6476	Remote Similarity	NPD6883	Approved
0.6458	Remote Similarity	NPD5133	Approved
0.6442	Remote Similarity	NPD6011	Approved
0.6442	Remote Similarity	NPD7320	Approved
0.6436	Remote Similarity	NPD5091	Approved
0.6415	Remote Similarity	NPD8130	Phase 1
0.6415	Remote Similarity	NPD6617	Approved
0.6415	Remote Similarity	NPD6847	Approved
0.6415	Remote Similarity	NPD6649	Approved
0.6415	Remote Similarity	NPD6869	Approved
0.6415	Remote Similarity	NPD6650	Approved
0.6413	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6408	Remote Similarity	NPD6008	Approved
0.6404	Remote Similarity	NPD7525	Registered
0.6404	Remote Similarity	NPD7514	Phase 3
0.6395	Remote Similarity	NPD5275	Approved
0.6395	Remote Similarity	NPD4190	Phase 3
0.6392	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6392	Remote Similarity	NPD7900	Approved
0.6392	Remote Similarity	NPD7748	Approved
0.6381	Remote Similarity	NPD6373	Approved
0.6381	Remote Similarity	NPD6372	Approved
0.6381	Remote Similarity	NPD6012	Approved
0.6381	Remote Similarity	NPD6013	Approved
0.6381	Remote Similarity	NPD6014	Approved
0.6373	Remote Similarity	NPD4754	Approved
0.6364	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD5959	Approved
0.6355	Remote Similarity	NPD6882	Approved
0.6355	Remote Similarity	NPD8297	Approved
0.6354	Remote Similarity	NPD7637	Suspended
0.6354	Remote Similarity	NPD7515	Phase 2
0.6346	Remote Similarity	NPD5701	Approved
0.6322	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.631	Remote Similarity	NPD7143	Approved
0.631	Remote Similarity	NPD7144	Approved
0.6286	Remote Similarity	NPD4730	Approved
0.6286	Remote Similarity	NPD4729	Approved
0.6279	Remote Similarity	NPD6926	Approved
0.6279	Remote Similarity	NPD6924	Approved
0.6277	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6265	Remote Similarity	NPD5360	Phase 3
0.6265	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.6262	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.625	Remote Similarity	NPD4767	Approved
0.625	Remote Similarity	NPD4768	Approved
0.625	Remote Similarity	NPD6932	Approved
0.625	Remote Similarity	NPD5785	Approved
0.6238	Remote Similarity	NPD6404	Discontinued
0.6235	Remote Similarity	NPD7150	Approved
0.6235	Remote Similarity	NPD7151	Approved
0.6235	Remote Similarity	NPD7152	Approved
0.6228	Remote Similarity	NPD7457	Clinical (unspecified phase)
0.6222	Remote Similarity	NPD7332	Phase 2
0.62	Remote Similarity	NPD7902	Approved
0.6196	Remote Similarity	NPD5362	Discontinued
0.619	Remote Similarity	NPD6412	Phase 2
0.619	Remote Similarity	NPD6922	Approved
0.619	Remote Similarity	NPD6923	Approved
0.6186	Remote Similarity	NPD8034	Phase 2
0.6186	Remote Similarity	NPD8035	Phase 2
0.618	Remote Similarity	NPD7145	Approved
0.6168	Remote Similarity	NPD5250	Approved
0.6168	Remote Similarity	NPD5249	Phase 3
0.6168	Remote Similarity	NPD4634	Approved
0.6168	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6168	Remote Similarity	NPD5169	Approved
0.6168	Remote Similarity	NPD5248	Approved
0.6168	Remote Similarity	NPD5251	Approved
0.6168	Remote Similarity	NPD5135	Approved
0.6168	Remote Similarity	NPD5247	Approved
0.6154	Remote Similarity	NPD6902	Approved
0.6147	Remote Similarity	NPD4632	Approved
0.6146	Remote Similarity	NPD7285	Clinical (unspecified phase)

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