NPASS Compound

Structure

NPC472479 OpenBabel07101718292D 22 25 0 0 1 0 0 0 0 0999 V2000 2.2601 -1.2601 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3998 1.9254 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3997 1.9105 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2321 -1.0185 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4942 -0.0373 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6397 1.0707 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7148 -1.0829 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5050 0.6827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8653 -0.3880 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0108 0.7200 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2172 -1.6034 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3090 -0.9511 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3090 -0.9511 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2579 0.7014 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.6182 -0.3693 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8868 1.0520 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2471 -0.0187 0.0000 C 0 0 1 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 0.5000 -1.5388 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.5878 0.8090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.0423 -2.3790 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 13 2 0 0 0 0 2 17 1 0 0 0 0 3 17 1 0 0 0 0 5 8 1 0 0 0 0 5 9 1 0 0 0 0 6 10 1 0 0 0 0 6 14 1 0 0 0 0 7 11 1 0 0 0 0 7 15 2 0 0 0 0 8 17 1 0 0 0 0 9 18 1 0 0 0 0 11 20 1 0 0 0 0 12 19 1 0 0 0 0 12 20 1 0 0 0 0 13 16 1 0 0 0 0 13 20 1 0 0 0 0 14 17 1 0 0 0 0 14 18 1 1 0 0 0 15 18 1 0 0 0 0 15 19 1 0 0 0 0 16 19 1 0 0 0 0 16 21 2 0 0 0 0 18 4 1 1 0 0 0 19 10 1 1 0 0 0 20 22 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	300.21
Volume:	329.921
LogP:	3.292
LogD:	2.817
LogS:	-4.529
# Rotatable Bonds:	0
TPSA:	37.3
# H-Bond Aceptor:	2
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.538
Synthetic Accessibility Score:	5.806
Fsp3:	0.75
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	2
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.671
MDCK Permeability:	2.268053503939882e-05
Pgp-inhibitor:	0.014
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.55
30% Bioavailability (F30%):	0.008

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.468
Plasma Protein Binding (PPB):	89.50774383544922%
Volume Distribution (VD):	1.041
Pgp-substrate:	13.804519653320312%

ADMET: Metabolism

CYP1A2-inhibitor:	0.031
CYP1A2-substrate:	0.882
CYP2C19-inhibitor:	0.416
CYP2C19-substrate:	0.882
CYP2C9-inhibitor:	0.328
CYP2C9-substrate:	0.405
CYP2D6-inhibitor:	0.031
CYP2D6-substrate:	0.107
CYP3A4-inhibitor:	0.79
CYP3A4-substrate:	0.466

ADMET: Excretion

Clearance (CL):	3.326
Half-life (T1/2):	0.195

ADMET: Toxicity

hERG Blockers:	0.003
Human Hepatotoxicity (H-HT):	0.406
Drug-inuced Liver Injury (DILI):	0.057
AMES Toxicity:	0.084
Rat Oral Acute Toxicity:	0.469
Maximum Recommended Daily Dose:	0.879
Skin Sensitization:	0.124
Carcinogencity:	0.421
Eye Corrosion:	0.121
Eye Irritation:	0.361
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: NPC472479

Natural Product ID:	NPC472479
*Common Name:**	DGKNOMBMBJXZGO-DMSXTEQDSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	DGKNOMBMBJXZGO-DMSXTEQDSA-N
Standard InCHI:	InChI=1S/C20H28O2/c1-13-16(21)19-10-6-14-17(2,3)8-5-9-18(14,4)15(19)7-11-20(13,22)12-19/h7,14,22H,1,5-6,8-12H2,2-4H3/t14-,18-,19-,20+/m1/s1
SMILES:	O=C1C(=C)[C@]2(C[C@]31CC[C@H]1[C@@](C3=CC2)(C)CCCC1(C)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3426487
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0003782] Kaurane diterpenoids

*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
NPO32442	jungermannia fauriana	Species	Jungermanniaceae	Eukaryota	n.a.	Guangxi Zhuang Autonomous Region, China	n.a.	PMID[25856683]

☑ 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	14

Activity Type	# Activity
Cell Line	6
NON-MOLECULAR	7
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2410	Cell Line	NCI-H1299	Homo sapiens	IC50	=	2400.0	nM	PMID[543652]
NPT114	Cell Line	LoVo	Homo sapiens	IC50	=	1800.0	nM	PMID[543652]
NPT111	Cell Line	K562	Homo sapiens	IC50	=	1900.0	nM	PMID[543652]
NPT90	Cell Line	DU-145	Homo sapiens	IC50	=	5500.0	nM	PMID[543652]
NPT858	Cell Line	LNCaP	Homo sapiens	IC50	=	3200.0	nM	PMID[543652]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	IC50	=	4200.0	nM	PMID[543652]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	1800.0	nM	PMID[543652]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	1700.0	nM	PMID[543652]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	1000.0	nM	PMID[543652]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	1200.0	nM	PMID[543652]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	3800.0	nM	PMID[543652]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	1300.0	nM	PMID[543652]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	3200.0	nM	PMID[543652]
NPT27	Others	Unspecified		IC50	=	6200.0	nM	PMID[543652]

☑ 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 NPC472479 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	164
0.1-0.2	1268
0.2-0.3	5805
0.3-0.4	14534
0.4-0.5	8495
0.5-0.6	6777
0.6-0.7	4328
0.7-0.8	1232
0.8-0.85	77
0.85-0.9	11
0.9-0.95	2
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9639	High Similarity	NPC472477
0.9639	High Similarity	NPC472475
0.9524	High Similarity	NPC472476
0.9512	High Similarity	NPC472488
0.9268	High Similarity	NPC472480
0.9176	High Similarity	NPC472489
0.8941	High Similarity	NPC472481
0.8941	High Similarity	NPC472484
0.8941	High Similarity	NPC472482
0.8837	High Similarity	NPC472483
0.869	High Similarity	NPC472492
0.8571	High Similarity	NPC193347
0.8409	Intermediate Similarity	NPC328313
0.8391	Intermediate Similarity	NPC472491
0.8391	Intermediate Similarity	NPC472494
0.8372	Intermediate Similarity	NPC144258
0.8333	Intermediate Similarity	NPC472478
0.8333	Intermediate Similarity	NPC469637
0.8333	Intermediate Similarity	NPC476809
0.8315	Intermediate Similarity	NPC262043
0.8295	Intermediate Similarity	NPC472493
0.8295	Intermediate Similarity	NPC136948
0.8261	Intermediate Similarity	NPC472485
0.8242	Intermediate Similarity	NPC474807
0.8222	Intermediate Similarity	NPC48010
0.8214	Intermediate Similarity	NPC170394
0.8214	Intermediate Similarity	NPC215843
0.8202	Intermediate Similarity	NPC48107
0.8202	Intermediate Similarity	NPC471791
0.8202	Intermediate Similarity	NPC471793
0.8202	Intermediate Similarity	NPC53911
0.8193	Intermediate Similarity	NPC266193
0.8193	Intermediate Similarity	NPC257666
0.8182	Intermediate Similarity	NPC474732
0.8182	Intermediate Similarity	NPC31564
0.8182	Intermediate Similarity	NPC474733
0.8182	Intermediate Similarity	NPC145879
0.8182	Intermediate Similarity	NPC469994
0.8182	Intermediate Similarity	NPC474778
0.8161	Intermediate Similarity	NPC59453
0.8161	Intermediate Similarity	NPC221758
0.814	Intermediate Similarity	NPC151519
0.8132	Intermediate Similarity	NPC475806
0.8111	Intermediate Similarity	NPC2983
0.8111	Intermediate Similarity	NPC309603
0.8111	Intermediate Similarity	NPC76879
0.8111	Intermediate Similarity	NPC472971
0.8111	Intermediate Similarity	NPC119416
0.8111	Intermediate Similarity	NPC472970
0.8111	Intermediate Similarity	NPC473999
0.8095	Intermediate Similarity	NPC471409
0.8095	Intermediate Similarity	NPC275494
0.8095	Intermediate Similarity	NPC207772
0.809	Intermediate Similarity	NPC58063
0.809	Intermediate Similarity	NPC471792
0.809	Intermediate Similarity	NPC475740
0.8068	Intermediate Similarity	NPC469948
0.8068	Intermediate Similarity	NPC474218
0.8068	Intermediate Similarity	NPC29447
0.8068	Intermediate Similarity	NPC471224
0.8065	Intermediate Similarity	NPC271195
0.8046	Intermediate Similarity	NPC477852
0.8046	Intermediate Similarity	NPC477373
0.8043	Intermediate Similarity	NPC109305
0.8043	Intermediate Similarity	NPC474736
0.8023	Intermediate Similarity	NPC14151
0.8023	Intermediate Similarity	NPC473217
0.8023	Intermediate Similarity	NPC147066
0.8	Intermediate Similarity	NPC472490
0.8	Intermediate Similarity	NPC471724
0.8	Intermediate Similarity	NPC72397
0.8	Intermediate Similarity	NPC7232
0.8	Intermediate Similarity	NPC474677
0.7979	Intermediate Similarity	NPC471463
0.7978	Intermediate Similarity	NPC194417
0.7978	Intermediate Similarity	NPC472974
0.7978	Intermediate Similarity	NPC470955
0.7978	Intermediate Similarity	NPC51014
0.7978	Intermediate Similarity	NPC20688
0.7957	Intermediate Similarity	NPC8993
0.7957	Intermediate Similarity	NPC292793
0.7955	Intermediate Similarity	NPC161423
0.7955	Intermediate Similarity	NPC329043
0.7955	Intermediate Similarity	NPC227064
0.7955	Intermediate Similarity	NPC82902
0.7955	Intermediate Similarity	NPC237712
0.7955	Intermediate Similarity	NPC472265
0.7955	Intermediate Similarity	NPC476412
0.7955	Intermediate Similarity	NPC58841
0.7955	Intermediate Similarity	NPC214043
0.7955	Intermediate Similarity	NPC321187
0.7955	Intermediate Similarity	NPC85774
0.7938	Intermediate Similarity	NPC87351
0.7935	Intermediate Similarity	NPC204341
0.7935	Intermediate Similarity	NPC473998
0.7931	Intermediate Similarity	NPC320514
0.7931	Intermediate Similarity	NPC46881
0.7931	Intermediate Similarity	NPC260956
0.7917	Intermediate Similarity	NPC154072
0.7912	Intermediate Similarity	NPC186688
0.7912	Intermediate Similarity	NPC26959
0.7912	Intermediate Similarity	NPC268406
0.7912	Intermediate Similarity	NPC310010
0.7912	Intermediate Similarity	NPC31985
0.7912	Intermediate Similarity	NPC477943
0.7912	Intermediate Similarity	NPC326627
0.7912	Intermediate Similarity	NPC1015
0.7912	Intermediate Similarity	NPC32830
0.7912	Intermediate Similarity	NPC474245
0.7907	Intermediate Similarity	NPC2482
0.7907	Intermediate Similarity	NPC108955
0.7907	Intermediate Similarity	NPC45495
0.7889	Intermediate Similarity	NPC165895
0.7889	Intermediate Similarity	NPC96496
0.7889	Intermediate Similarity	NPC317590
0.7889	Intermediate Similarity	NPC93778
0.7882	Intermediate Similarity	NPC476808
0.7882	Intermediate Similarity	NPC19443
0.7872	Intermediate Similarity	NPC197158
0.7872	Intermediate Similarity	NPC471624
0.7865	Intermediate Similarity	NPC474083
0.7865	Intermediate Similarity	NPC269638
0.7865	Intermediate Similarity	NPC179006
0.7865	Intermediate Similarity	NPC102292
0.7865	Intermediate Similarity	NPC474853
0.7857	Intermediate Similarity	NPC76966
0.7857	Intermediate Similarity	NPC311612
0.7857	Intermediate Similarity	NPC7629
0.7857	Intermediate Similarity	NPC151622
0.7857	Intermediate Similarity	NPC186554
0.7857	Intermediate Similarity	NPC472305
0.7849	Intermediate Similarity	NPC233118
0.7841	Intermediate Similarity	NPC471036
0.7841	Intermediate Similarity	NPC105803
0.7841	Intermediate Similarity	NPC291320
0.7835	Intermediate Similarity	NPC81530
0.7826	Intermediate Similarity	NPC69622
0.7826	Intermediate Similarity	NPC320026
0.7816	Intermediate Similarity	NPC150506
0.7816	Intermediate Similarity	NPC116797
0.7816	Intermediate Similarity	NPC201912
0.7816	Intermediate Similarity	NPC278459
0.7816	Intermediate Similarity	NPC121984
0.7816	Intermediate Similarity	NPC477372
0.7816	Intermediate Similarity	NPC55869
0.7816	Intermediate Similarity	NPC38350
0.7816	Intermediate Similarity	NPC164210
0.7812	Intermediate Similarity	NPC103051
0.7805	Intermediate Similarity	NPC84790
0.7805	Intermediate Similarity	NPC144627
0.7802	Intermediate Similarity	NPC117122
0.7802	Intermediate Similarity	NPC58271
0.7802	Intermediate Similarity	NPC471722
0.7802	Intermediate Similarity	NPC328539
0.78	Intermediate Similarity	NPC185
0.7791	Intermediate Similarity	NPC477371
0.7791	Intermediate Similarity	NPC474113
0.7789	Intermediate Similarity	NPC117133
0.7789	Intermediate Similarity	NPC29152
0.7778	Intermediate Similarity	NPC222613
0.7778	Intermediate Similarity	NPC472869
0.7778	Intermediate Similarity	NPC327115
0.7778	Intermediate Similarity	NPC475022
0.7778	Intermediate Similarity	NPC473168
0.7778	Intermediate Similarity	NPC155011
0.7778	Intermediate Similarity	NPC118648
0.7778	Intermediate Similarity	NPC94666
0.7765	Intermediate Similarity	NPC212661
0.7765	Intermediate Similarity	NPC34110
0.7765	Intermediate Similarity	NPC97377
0.7765	Intermediate Similarity	NPC106078
0.7765	Intermediate Similarity	NPC471035
0.7765	Intermediate Similarity	NPC165711
0.7755	Intermediate Similarity	NPC473424
0.7755	Intermediate Similarity	NPC136289
0.7755	Intermediate Similarity	NPC477915
0.7753	Intermediate Similarity	NPC473246
0.7753	Intermediate Similarity	NPC33913
0.7753	Intermediate Similarity	NPC251170
0.7753	Intermediate Similarity	NPC164577
0.7742	Intermediate Similarity	NPC131872
0.7742	Intermediate Similarity	NPC272746
0.7738	Intermediate Similarity	NPC476795
0.7727	Intermediate Similarity	NPC133391
0.7727	Intermediate Similarity	NPC469325
0.7727	Intermediate Similarity	NPC472239
0.7717	Intermediate Similarity	NPC472973
0.7717	Intermediate Similarity	NPC472676
0.7717	Intermediate Similarity	NPC472688
0.7717	Intermediate Similarity	NPC474570
0.7711	Intermediate Similarity	NPC247586
0.7708	Intermediate Similarity	NPC156546
0.7708	Intermediate Similarity	NPC126815
0.7708	Intermediate Similarity	NPC170131
0.7708	Intermediate Similarity	NPC107243
0.77	Intermediate Similarity	NPC166607
0.77	Intermediate Similarity	NPC149047
0.77	Intermediate Similarity	NPC257353
0.7692	Intermediate Similarity	NPC90652
0.7692	Intermediate Similarity	NPC136548

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 NPC472479 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	157
0.1-0.2	1605
0.2-0.3	4148
0.3-0.4	2241
0.4-0.5	563
0.5-0.6	146
0.6-0.7	171
0.7-0.8	98
0.8-0.85	16
0.85-0.9	5
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8605	High Similarity	NPD3574	Clinical (unspecified phase)
0.8571	High Similarity	NPD4221	Approved
0.8571	High Similarity	NPD4223	Phase 3
0.8372	Intermediate Similarity	NPD4197	Approved
0.8276	Intermediate Similarity	NPD5329	Approved
0.8182	Intermediate Similarity	NPD4138	Approved
0.8182	Intermediate Similarity	NPD5205	Approved
0.8182	Intermediate Similarity	NPD4689	Approved
0.8182	Intermediate Similarity	NPD4688	Approved
0.8182	Intermediate Similarity	NPD4693	Phase 3
0.8182	Intermediate Similarity	NPD4690	Approved
0.8182	Intermediate Similarity	NPD5690	Phase 2
0.8161	Intermediate Similarity	NPD4786	Approved
0.814	Intermediate Similarity	NPD3667	Approved
0.8	Intermediate Similarity	NPD4195	Approved
0.7978	Intermediate Similarity	NPD5280	Approved
0.7978	Intermediate Similarity	NPD4623	Approved
0.7978	Intermediate Similarity	NPD4519	Discontinued
0.7978	Intermediate Similarity	NPD3618	Phase 1
0.7978	Intermediate Similarity	NPD4694	Approved
0.7955	Intermediate Similarity	NPD3665	Phase 1
0.7955	Intermediate Similarity	NPD3666	Approved
0.7955	Intermediate Similarity	NPD3133	Approved
0.7912	Intermediate Similarity	NPD4753	Phase 2
0.7907	Intermediate Similarity	NPD4695	Discontinued
0.7882	Intermediate Similarity	NPD3617	Approved
0.7872	Intermediate Similarity	NPD5210	Approved
0.7872	Intermediate Similarity	NPD4629	Approved
0.7849	Intermediate Similarity	NPD4202	Approved
0.7816	Intermediate Similarity	NPD4139	Approved
0.7816	Intermediate Similarity	NPD4692	Approved
0.7755	Intermediate Similarity	NPD5211	Phase 2
0.7742	Intermediate Similarity	NPD5281	Approved
0.7742	Intermediate Similarity	NPD6079	Approved
0.7742	Intermediate Similarity	NPD5284	Approved
0.7717	Intermediate Similarity	NPD5328	Approved
0.766	Intermediate Similarity	NPD6399	Phase 3
0.764	Intermediate Similarity	NPD4788	Approved
0.76	Intermediate Similarity	NPD5141	Approved
0.7556	Intermediate Similarity	NPD3668	Phase 3
0.7551	Intermediate Similarity	NPD5286	Approved
0.7551	Intermediate Similarity	NPD5285	Approved
0.7551	Intermediate Similarity	NPD4696	Approved
0.7526	Intermediate Similarity	NPD4755	Approved
0.7475	Intermediate Similarity	NPD5223	Approved
0.7474	Intermediate Similarity	NPD5133	Approved
0.747	Intermediate Similarity	NPD4691	Approved
0.747	Intermediate Similarity	NPD4747	Approved
0.7449	Intermediate Similarity	NPD5696	Approved
0.7447	Intermediate Similarity	NPD4096	Approved
0.7423	Intermediate Similarity	NPD4697	Phase 3
0.7423	Intermediate Similarity	NPD5222	Approved
0.7423	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7423	Intermediate Similarity	NPD5221	Approved
0.7419	Intermediate Similarity	NPD5208	Approved
0.7419	Intermediate Similarity	NPD4518	Approved
0.7412	Intermediate Similarity	NPD4785	Approved
0.7412	Intermediate Similarity	NPD4784	Approved
0.74	Intermediate Similarity	NPD5225	Approved
0.74	Intermediate Similarity	NPD5091	Approved
0.74	Intermediate Similarity	NPD4633	Approved
0.74	Intermediate Similarity	NPD5226	Approved
0.74	Intermediate Similarity	NPD5224	Approved
0.7391	Intermediate Similarity	NPD5279	Phase 3
0.7391	Intermediate Similarity	NPD6098	Approved
0.7381	Intermediate Similarity	NPD4243	Approved
0.7374	Intermediate Similarity	NPD4700	Approved
0.7368	Intermediate Similarity	NPD5693	Phase 1
0.7349	Intermediate Similarity	NPD4137	Phase 3
0.7347	Intermediate Similarity	NPD6083	Phase 2
0.7347	Intermediate Similarity	NPD5173	Approved
0.7347	Intermediate Similarity	NPD6084	Phase 2
0.734	Intermediate Similarity	NPD6080	Approved
0.734	Intermediate Similarity	NPD6904	Approved
0.734	Intermediate Similarity	NPD6673	Approved
0.7327	Intermediate Similarity	NPD5175	Approved
0.7327	Intermediate Similarity	NPD5174	Approved
0.732	Intermediate Similarity	NPD5695	Phase 3
0.7315	Intermediate Similarity	NPD7115	Discovery
0.7263	Intermediate Similarity	NPD5207	Approved
0.7241	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7238	Intermediate Similarity	NPD4634	Approved
0.7216	Intermediate Similarity	NPD6001	Approved
0.7209	Intermediate Similarity	NPD4058	Approved
0.7204	Intermediate Similarity	NPD7521	Approved
0.7204	Intermediate Similarity	NPD7334	Approved
0.7204	Intermediate Similarity	NPD6684	Approved
0.7204	Intermediate Similarity	NPD7146	Approved
0.7204	Intermediate Similarity	NPD6409	Approved
0.7204	Intermediate Similarity	NPD5330	Approved
0.7158	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.7157	Intermediate Similarity	NPD4754	Approved
0.7143	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7128	Intermediate Similarity	NPD4751	Clinical (unspecified phase)
0.7128	Intermediate Similarity	NPD3573	Approved
0.7126	Intermediate Similarity	NPD7339	Approved
0.7126	Intermediate Similarity	NPD5275	Approved
0.7126	Intermediate Similarity	NPD4190	Phase 3
0.7126	Intermediate Similarity	NPD6942	Approved
0.7115	Intermediate Similarity	NPD5697	Approved
0.7083	Intermediate Similarity	NPD5692	Phase 3
0.7053	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7053	Intermediate Similarity	NPD6672	Approved
0.7053	Intermediate Similarity	NPD6903	Approved
0.7053	Intermediate Similarity	NPD5737	Approved
0.7048	Intermediate Similarity	NPD4729	Approved
0.7048	Intermediate Similarity	NPD4730	Approved
0.7048	Intermediate Similarity	NPD5128	Approved
0.7048	Intermediate Similarity	NPD6011	Approved
0.7048	Intermediate Similarity	NPD6881	Approved
0.7048	Intermediate Similarity	NPD6899	Approved
0.7024	Intermediate Similarity	NPD5361	Clinical (unspecified phase)
0.7024	Intermediate Similarity	NPD3621	Clinical (unspecified phase)
0.7024	Intermediate Similarity	NPD5360	Phase 3
0.7019	Intermediate Similarity	NPD7128	Approved
0.7019	Intermediate Similarity	NPD4767	Approved
0.7019	Intermediate Similarity	NPD5739	Approved
0.7019	Intermediate Similarity	NPD4768	Approved
0.7019	Intermediate Similarity	NPD6675	Approved
0.7019	Intermediate Similarity	NPD6402	Approved
0.7011	Intermediate Similarity	NPD5733	Approved
0.7011	Intermediate Similarity	NPD4687	Approved
0.701	Intermediate Similarity	NPD5694	Approved
0.701	Intermediate Similarity	NPD6050	Approved
0.701	Intermediate Similarity	NPD7515	Phase 2
0.7009	Intermediate Similarity	NPD6649	Approved
0.7009	Intermediate Similarity	NPD6650	Approved
0.6981	Remote Similarity	NPD6012	Approved
0.6981	Remote Similarity	NPD6013	Approved
0.6981	Remote Similarity	NPD6372	Approved
0.6981	Remote Similarity	NPD6014	Approved
0.6981	Remote Similarity	NPD6373	Approved
0.6977	Remote Similarity	NPD5276	Approved
0.6952	Remote Similarity	NPD5701	Approved
0.6916	Remote Similarity	NPD5169	Approved
0.6916	Remote Similarity	NPD5135	Approved
0.6916	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6916	Remote Similarity	NPD5251	Approved
0.6916	Remote Similarity	NPD5248	Approved
0.6916	Remote Similarity	NPD6883	Approved
0.6916	Remote Similarity	NPD5249	Phase 3
0.6916	Remote Similarity	NPD7290	Approved
0.6916	Remote Similarity	NPD5250	Approved
0.6916	Remote Similarity	NPD5247	Approved
0.6916	Remote Similarity	NPD7102	Approved
0.6915	Remote Similarity	NPD1696	Phase 3
0.6887	Remote Similarity	NPD7320	Approved
0.6869	Remote Similarity	NPD7748	Approved
0.6863	Remote Similarity	NPD6404	Discontinued
0.6857	Remote Similarity	NPD6008	Approved
0.6852	Remote Similarity	NPD5127	Approved
0.6852	Remote Similarity	NPD8130	Phase 1
0.6852	Remote Similarity	NPD5215	Approved
0.6852	Remote Similarity	NPD5217	Approved
0.6852	Remote Similarity	NPD6617	Approved
0.6852	Remote Similarity	NPD6869	Approved
0.6852	Remote Similarity	NPD6847	Approved
0.6852	Remote Similarity	NPD5216	Approved
0.6832	Remote Similarity	NPD7902	Approved
0.68	Remote Similarity	NPD5654	Approved
0.6789	Remote Similarity	NPD6882	Approved
0.6789	Remote Similarity	NPD8297	Approved
0.6786	Remote Similarity	NPD4224	Phase 2
0.6782	Remote Similarity	NPD4758	Discontinued
0.6765	Remote Similarity	NPD4225	Approved
0.6739	Remote Similarity	NPD4748	Discontinued
0.6739	Remote Similarity	NPD7525	Registered
0.6737	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6737	Remote Similarity	NPD5363	Approved
0.6735	Remote Similarity	NPD5785	Approved
0.6733	Remote Similarity	NPD7614	Phase 1
0.6729	Remote Similarity	NPD5168	Approved
0.6727	Remote Similarity	NPD4632	Approved
0.6699	Remote Similarity	NPD7640	Approved
0.6699	Remote Similarity	NPD7639	Approved
0.6697	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5959	Approved
0.6667	Remote Similarity	NPD6054	Approved
0.6667	Remote Similarity	NPD5167	Approved
0.6667	Remote Similarity	NPD6319	Approved
0.6667	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6052	Approved
0.6667	Remote Similarity	NPD7341	Phase 2
0.6636	Remote Similarity	NPD6614	Approved
0.6629	Remote Similarity	NPD6924	Approved
0.6629	Remote Similarity	NPD6926	Approved
0.6609	Remote Similarity	NPD6015	Approved
0.6609	Remote Similarity	NPD6016	Approved
0.6607	Remote Similarity	NPD6274	Approved
0.6602	Remote Similarity	NPD7638	Approved
0.6596	Remote Similarity	NPD4270	Approved
0.6596	Remote Similarity	NPD4269	Approved
0.6596	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6591	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6591	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6588	Remote Similarity	NPD7331	Phase 2
0.6579	Remote Similarity	NPD4522	Approved
0.6562	Remote Similarity	NPD1694	Approved
0.6559	Remote Similarity	NPD6931	Approved
0.6559	Remote Similarity	NPD6930	Phase 2

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