NPASS Compound

Structure

NPC474231 OpenBabel07101719252D 30 34 0 0 1 0 0 0 0 0999 V2000 -1.5872 6.3296 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2185 5.7996 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9752 4.4460 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9318 2.4440 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3125 1.8950 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8576 0.4952 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5729 -0.4952 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5729 -1.4855 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6065 3.9159 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3005 2.9741 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2392 0.4952 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6571 -0.3060 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.9903 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7153 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7153 -1.9806 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8576 1.4855 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.9806 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8576 -1.4855 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2499 5.5937 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9438 4.6519 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.9631 2.2382 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.6571 1.2963 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7153 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7153 0.9903 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8576 -0.4952 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8576 -1.4855 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8576 -0.4952 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8576 -0.4952 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 19 1 0 0 0 0 2 19 1 0 0 0 0 6 26 1 0 0 0 0 7 8 1 0 0 0 0 7 14 1 0 0 0 0 8 15 1 0 0 0 0 9 10 2 0 0 0 0 9 20 1 0 0 0 0 10 21 1 0 0 0 0 11 12 1 0 0 0 0 11 22 1 0 0 0 0 12 23 1 0 0 0 0 13 16 1 0 0 0 0 13 24 1 0 0 0 0 14 26 1 0 0 0 0 15 27 1 0 0 0 0 16 25 1 0 0 0 0 17 18 2 0 0 0 0 17 27 1 0 0 0 0 18 28 1 0 0 0 0 19 20 1 0 0 0 0 20 3 1 1 0 0 0 21 4 1 6 0 0 0 21 22 1 0 0 0 0 22 25 1 6 0 0 0 23 25 1 6 0 0 0 23 28 1 0 0 0 0 24 26 1 6 0 0 0 24 28 1 0 0 0 0 25 5 1 6 0 0 0 26 27 1 6 0 0 0 27 29 1 1 0 0 0 28 30 1 1 0 0 0 29 30 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	412.33
Volume:	462.369
LogP:	7.102
LogD:	5.514
LogS:	-7.032
# Rotatable Bonds:	4
TPSA:	18.46
# H-Bond Aceptor:	2
# H-Bond Donor:	0
# Rings:	6
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.351
Synthetic Accessibility Score:	6.597
Fsp3:	0.857
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.871
MDCK Permeability:	1.9583643734222278e-05
Pgp-inhibitor:	0.018
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.041
30% Bioavailability (F30%):	0.267

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.015
Plasma Protein Binding (PPB):	90.5249252319336%
Volume Distribution (VD):	1.231
Pgp-substrate:	2.3136332035064697%

ADMET: Metabolism

CYP1A2-inhibitor:	0.053
CYP1A2-substrate:	0.944
CYP2C19-inhibitor:	0.23
CYP2C19-substrate:	0.966
CYP2C9-inhibitor:	0.273
CYP2C9-substrate:	0.055
CYP2D6-inhibitor:	0.246
CYP2D6-substrate:	0.283
CYP3A4-inhibitor:	0.912
CYP3A4-substrate:	0.929

ADMET: Excretion

Clearance (CL):	2.31
Half-life (T1/2):	0.073

ADMET: Toxicity

hERG Blockers:	0.849
Human Hepatotoxicity (H-HT):	0.912
Drug-inuced Liver Injury (DILI):	0.022
AMES Toxicity:	0.003
Rat Oral Acute Toxicity:	0.756
Maximum Recommended Daily Dose:	0.939
Skin Sensitization:	0.265
Carcinogencity:	0.007
Eye Corrosion:	0.008
Eye Irritation:	0.069
Respiratory Toxicity:	0.913

Download Data

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

Natural Product: NPC474231

Natural Product ID:	NPC474231
*Common Name:**	UCQJLPOKKJIZQU-ROIBAQGNSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	UCQJLPOKKJIZQU-ROIBAQGNSA-N
Standard InCHI:	InChI=1S/C28H44O2/c1-19(2)20(3)9-10-21(4)22-11-12-23-25(22,5)16-13-24-26(6)14-7-8-15-27(26)17-18-28(23,24)30-29-27/h9-10,17-24H,7-8,11-16H2,1-6H3/b10-9+/t20-,21+,22+,23+,24+,25+,26+,27-,28-/m0/s1
SMILES:	CC(C)C(C)C=CC(C)C1CCC2C1(CCC3C24C=CC5(C3(CCCC5)C)OO4)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL463901
PubChem CID:	44566505
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0003567] Ergostane steroids

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO32840	topsentia sp.	Species	n.a.	Eukaryota	n.a.	At the 20 m depth, the coast of Jeju Island, Korea	2002-OCT	PMID[16643027]
NPO32840	topsentia sp.	Species	n.a.	Eukaryota	n.a.	the coast of Jeju Island, Korea	2002-OCT	PMID[16643027]
NPO32840	topsentia sp.	Species	n.a.	Eukaryota	n.a.	n.a.	n.a.	PMID[17190456]
NPO32840	topsentia sp.	Species	n.a.	Eukaryota	n.a.	n.a.	n.a.	PMID[19653640]
NPO32840	topsentia sp.	Species	n.a.	Eukaryota	n.a.	n.a.	n.a.	PMID[2045823]
NPO32840	topsentia sp.	Species	n.a.	Eukaryota	n.a.	n.a.	n.a.	PMID[20806907]
NPO32840	topsentia sp.	Species	n.a.	Eukaryota	n.a.	n.a.	n.a.	PMID[8145229]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
ED50	5

Activity Type	# Activity
Cell Line	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	ED50	=	17.5	ug ml-1	PMID[471010]
NPT146	Cell Line	SK-OV-3	Homo sapiens	ED50	=	17.8	ug ml-1	PMID[471010]
NPT147	Cell Line	SK-MEL-2	Homo sapiens	ED50	=	19.4	ug ml-1	PMID[471010]
NPT574	Cell Line	XF498	Homo sapiens	ED50	=	24.7	ug ml-1	PMID[471010]
NPT148	Cell Line	HCT-15	Homo sapiens	ED50	=	21.1	ug ml-1	PMID[471010]

☑ 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 NPC474231 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	271
0.1-0.2	1933
0.2-0.3	11519
0.3-0.4	14312
0.4-0.5	6122
0.5-0.6	5841
0.6-0.7	2353
0.7-0.8	329
0.8-0.85	8
0.85-0.9	7
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9583	High Similarity	NPC474230
0.9315	High Similarity	NPC475027
0.9315	High Similarity	NPC475025
0.8313	Intermediate Similarity	NPC212596
0.8313	Intermediate Similarity	NPC4574
0.8243	Intermediate Similarity	NPC475728
0.8214	Intermediate Similarity	NPC101886
0.8193	Intermediate Similarity	NPC304083
0.8171	Intermediate Similarity	NPC318390
0.8148	Intermediate Similarity	NPC134481
0.8125	Intermediate Similarity	NPC47761
0.8118	Intermediate Similarity	NPC14380
0.8095	Intermediate Similarity	NPC475605
0.8072	Intermediate Similarity	NPC299068
0.8049	Intermediate Similarity	NPC470077
0.8025	Intermediate Similarity	NPC49964
0.8025	Intermediate Similarity	NPC296701
0.8025	Intermediate Similarity	NPC218616
0.8025	Intermediate Similarity	NPC87489
0.8	Intermediate Similarity	NPC138974
0.7952	Intermediate Similarity	NPC470360
0.7927	Intermediate Similarity	NPC470558
0.7927	Intermediate Similarity	NPC82623
0.7907	Intermediate Similarity	NPC245410
0.7907	Intermediate Similarity	NPC470390
0.7907	Intermediate Similarity	NPC192437
0.7907	Intermediate Similarity	NPC270511
0.7901	Intermediate Similarity	NPC264245
0.7882	Intermediate Similarity	NPC133588
0.7875	Intermediate Similarity	NPC80530
0.7875	Intermediate Similarity	NPC209430
0.7875	Intermediate Similarity	NPC273410
0.7875	Intermediate Similarity	NPC30986
0.7857	Intermediate Similarity	NPC261266
0.7831	Intermediate Similarity	NPC231310
0.7831	Intermediate Similarity	NPC15534
0.7831	Intermediate Similarity	NPC205845
0.7805	Intermediate Similarity	NPC470049
0.7792	Intermediate Similarity	NPC259049
0.7778	Intermediate Similarity	NPC236237
0.7778	Intermediate Similarity	NPC322313
0.7778	Intermediate Similarity	NPC164840
0.7778	Intermediate Similarity	NPC209944
0.7778	Intermediate Similarity	NPC241290
0.7778	Intermediate Similarity	NPC102253
0.7778	Intermediate Similarity	NPC234193
0.775	Intermediate Similarity	NPC477514
0.775	Intermediate Similarity	NPC244385
0.775	Intermediate Similarity	NPC285761
0.775	Intermediate Similarity	NPC138621
0.775	Intermediate Similarity	NPC6978
0.775	Intermediate Similarity	NPC473943
0.775	Intermediate Similarity	NPC167037
0.7738	Intermediate Similarity	NPC137493
0.7738	Intermediate Similarity	NPC274448
0.7738	Intermediate Similarity	NPC157257
0.7722	Intermediate Similarity	NPC247325
0.7722	Intermediate Similarity	NPC134330
0.7722	Intermediate Similarity	NPC189883
0.7722	Intermediate Similarity	NPC129165
0.7722	Intermediate Similarity	NPC244488
0.7701	Intermediate Similarity	NPC291484
0.7701	Intermediate Similarity	NPC80561
0.7701	Intermediate Similarity	NPC329596
0.7701	Intermediate Similarity	NPC3345
0.7701	Intermediate Similarity	NPC11216
0.7701	Intermediate Similarity	NPC204188
0.7654	Intermediate Similarity	NPC81306
0.7654	Intermediate Similarity	NPC28862
0.7654	Intermediate Similarity	NPC1319
0.7654	Intermediate Similarity	NPC143182
0.7654	Intermediate Similarity	NPC47982
0.7654	Intermediate Similarity	NPC109546
0.7654	Intermediate Similarity	NPC84694
0.7647	Intermediate Similarity	NPC139724
0.7647	Intermediate Similarity	NPC6391
0.7625	Intermediate Similarity	NPC91594
0.7625	Intermediate Similarity	NPC214570
0.7625	Intermediate Similarity	NPC155986
0.7625	Intermediate Similarity	NPC318495
0.7625	Intermediate Similarity	NPC198968
0.7619	Intermediate Similarity	NPC238485
0.7619	Intermediate Similarity	NPC474047
0.7614	Intermediate Similarity	NPC97404
0.7614	Intermediate Similarity	NPC41554
0.7595	Intermediate Similarity	NPC141071
0.7595	Intermediate Similarity	NPC257347
0.7595	Intermediate Similarity	NPC471723
0.759	Intermediate Similarity	NPC50964
0.759	Intermediate Similarity	NPC202389
0.759	Intermediate Similarity	NPC30166
0.759	Intermediate Similarity	NPC101462
0.7586	Intermediate Similarity	NPC470361
0.7564	Intermediate Similarity	NPC474140
0.7561	Intermediate Similarity	NPC13554
0.7561	Intermediate Similarity	NPC236112
0.7558	Intermediate Similarity	NPC470620
0.7558	Intermediate Similarity	NPC149224
0.7531	Intermediate Similarity	NPC11908
0.7531	Intermediate Similarity	NPC474216
0.7531	Intermediate Similarity	NPC275910
0.75	Intermediate Similarity	NPC94192
0.75	Intermediate Similarity	NPC240604
0.75	Intermediate Similarity	NPC73875
0.75	Intermediate Similarity	NPC141941
0.75	Intermediate Similarity	NPC107059
0.75	Intermediate Similarity	NPC475789
0.75	Intermediate Similarity	NPC477818
0.75	Intermediate Similarity	NPC113733
0.75	Intermediate Similarity	NPC207013
0.75	Intermediate Similarity	NPC295668
0.75	Intermediate Similarity	NPC470384
0.75	Intermediate Similarity	NPC193870
0.75	Intermediate Similarity	NPC321381
0.75	Intermediate Similarity	NPC46160
0.75	Intermediate Similarity	NPC202642
0.75	Intermediate Similarity	NPC300324
0.75	Intermediate Similarity	NPC237460
0.75	Intermediate Similarity	NPC470749
0.75	Intermediate Similarity	NPC470362
0.75	Intermediate Similarity	NPC321016
0.75	Intermediate Similarity	NPC474634
0.75	Intermediate Similarity	NPC317458
0.7471	Intermediate Similarity	NPC474668
0.7471	Intermediate Similarity	NPC471952
0.747	Intermediate Similarity	NPC70927
0.747	Intermediate Similarity	NPC82986
0.747	Intermediate Similarity	NPC476646
0.747	Intermediate Similarity	NPC209620
0.747	Intermediate Similarity	NPC474683
0.747	Intermediate Similarity	NPC474759
0.747	Intermediate Similarity	NPC474731
0.747	Intermediate Similarity	NPC474531
0.747	Intermediate Similarity	NPC23852
0.747	Intermediate Similarity	NPC7505
0.747	Intermediate Similarity	NPC474752
0.7468	Intermediate Similarity	NPC201048
0.7468	Intermediate Similarity	NPC476366
0.7467	Intermediate Similarity	NPC279434
0.7444	Intermediate Similarity	NPC127718
0.7444	Intermediate Similarity	NPC65402
0.7442	Intermediate Similarity	NPC6605
0.7442	Intermediate Similarity	NPC24277
0.7439	Intermediate Similarity	NPC328714
0.7412	Intermediate Similarity	NPC475798
0.7412	Intermediate Similarity	NPC124172
0.7412	Intermediate Similarity	NPC478102
0.7412	Intermediate Similarity	NPC185568
0.7412	Intermediate Similarity	NPC469878
0.7412	Intermediate Similarity	NPC209802
0.7412	Intermediate Similarity	NPC127606
0.7407	Intermediate Similarity	NPC470711
0.7407	Intermediate Similarity	NPC470758
0.7407	Intermediate Similarity	NPC470750
0.7403	Intermediate Similarity	NPC476431
0.7381	Intermediate Similarity	NPC248886
0.7381	Intermediate Similarity	NPC189972
0.7381	Intermediate Similarity	NPC5985
0.7381	Intermediate Similarity	NPC20853
0.7375	Intermediate Similarity	NPC133580
0.7375	Intermediate Similarity	NPC230301
0.7375	Intermediate Similarity	NPC22105
0.7375	Intermediate Similarity	NPC288035
0.7375	Intermediate Similarity	NPC121744
0.7375	Intermediate Similarity	NPC304309
0.7375	Intermediate Similarity	NPC3403
0.7375	Intermediate Similarity	NPC32832
0.7375	Intermediate Similarity	NPC285893
0.7375	Intermediate Similarity	NPC118508
0.7375	Intermediate Similarity	NPC136188
0.7375	Intermediate Similarity	NPC28657
0.7375	Intermediate Similarity	NPC162742
0.7375	Intermediate Similarity	NPC134847
0.7375	Intermediate Similarity	NPC322353
0.7375	Intermediate Similarity	NPC291503
0.7363	Intermediate Similarity	NPC8774
0.7349	Intermediate Similarity	NPC96362
0.7349	Intermediate Similarity	NPC295131
0.7342	Intermediate Similarity	NPC182717
0.7333	Intermediate Similarity	NPC27531
0.7333	Intermediate Similarity	NPC310013
0.7326	Intermediate Similarity	NPC266511
0.7317	Intermediate Similarity	NPC205455
0.7317	Intermediate Similarity	NPC477522
0.7317	Intermediate Similarity	NPC65897
0.7317	Intermediate Similarity	NPC85346
0.7317	Intermediate Similarity	NPC18603
0.7317	Intermediate Similarity	NPC301707
0.7317	Intermediate Similarity	NPC475337
0.7317	Intermediate Similarity	NPC186191
0.7317	Intermediate Similarity	NPC76931
0.7317	Intermediate Similarity	NPC300499
0.7317	Intermediate Similarity	NPC302041
0.7317	Intermediate Similarity	NPC307965
0.7317	Intermediate Similarity	NPC87604
0.7303	Intermediate Similarity	NPC77796
0.7303	Intermediate Similarity	NPC476226
0.7303	Intermediate Similarity	NPC273199
0.7303	Intermediate Similarity	NPC92885
0.7303	Intermediate Similarity	NPC320026

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 NPC474231 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	226
0.1-0.2	2018
0.2-0.3	4702
0.3-0.4	1597
0.4-0.5	270
0.5-0.6	182
0.6-0.7	145
0.7-0.8	10
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7922	Intermediate Similarity	NPD4785	Approved
0.7922	Intermediate Similarity	NPD4784	Approved
0.7895	Intermediate Similarity	NPD4243	Approved
0.7778	Intermediate Similarity	NPD7525	Registered
0.7439	Intermediate Similarity	NPD4195	Approved
0.7375	Intermediate Similarity	NPD5275	Approved
0.7375	Intermediate Similarity	NPD7339	Approved
0.7375	Intermediate Similarity	NPD6942	Approved
0.7375	Intermediate Similarity	NPD4190	Phase 3
0.7073	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD6924	Approved
0.7037	Intermediate Similarity	NPD6926	Approved
0.7024	Intermediate Similarity	NPD7645	Phase 2
0.7	Intermediate Similarity	NPD6051	Approved
0.6977	Remote Similarity	NPD4223	Phase 3
0.6977	Remote Similarity	NPD4221	Approved
0.6966	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6932	Remote Similarity	NPD5329	Approved
0.6867	Remote Similarity	NPD6933	Approved
0.6854	Remote Similarity	NPD6098	Approved
0.6848	Remote Similarity	NPD6079	Approved
0.6818	Remote Similarity	NPD4786	Approved
0.6818	Remote Similarity	NPD4197	Approved
0.6813	Remote Similarity	NPD5328	Approved
0.6774	Remote Similarity	NPD4202	Approved
0.6744	Remote Similarity	NPD6930	Phase 2
0.6744	Remote Similarity	NPD6931	Approved
0.6744	Remote Similarity	NPD7514	Phase 3
0.6744	Remote Similarity	NPD7509	Discontinued
0.6706	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4690	Approved
0.6667	Remote Similarity	NPD4623	Approved
0.6667	Remote Similarity	NPD5690	Phase 2
0.6667	Remote Similarity	NPD3618	Phase 1
0.6667	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4688	Approved
0.6667	Remote Similarity	NPD5205	Approved
0.6667	Remote Similarity	NPD4519	Discontinued
0.6667	Remote Similarity	NPD4138	Approved
0.6667	Remote Similarity	NPD4689	Approved
0.6667	Remote Similarity	NPD7144	Approved
0.6667	Remote Similarity	NPD4747	Approved
0.6667	Remote Similarity	NPD4693	Phase 3
0.6667	Remote Similarity	NPD7143	Approved
0.6632	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.663	Remote Similarity	NPD6080	Approved
0.663	Remote Similarity	NPD6904	Approved
0.663	Remote Similarity	NPD6673	Approved
0.6629	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6628	Remote Similarity	NPD6929	Approved
0.6593	Remote Similarity	NPD3573	Approved
0.6591	Remote Similarity	NPD3667	Approved
0.6588	Remote Similarity	NPD6932	Approved
0.6585	Remote Similarity	NPD7150	Approved
0.6585	Remote Similarity	NPD7151	Approved
0.6585	Remote Similarity	NPD7152	Approved
0.6566	Remote Similarity	NPD5211	Phase 2
0.6552	Remote Similarity	NPD7332	Phase 2
0.6552	Remote Similarity	NPD4748	Discontinued
0.6543	Remote Similarity	NPD6923	Approved
0.6543	Remote Similarity	NPD6922	Approved
0.6543	Remote Similarity	NPD4137	Phase 3
0.6531	Remote Similarity	NPD4696	Approved
0.6531	Remote Similarity	NPD5286	Approved
0.6531	Remote Similarity	NPD5285	Approved
0.6526	Remote Similarity	NPD6001	Approved
0.6522	Remote Similarity	NPD4723	Approved
0.6522	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD5208	Approved
0.6522	Remote Similarity	NPD6672	Approved
0.6522	Remote Similarity	NPD4722	Approved
0.6522	Remote Similarity	NPD5737	Approved
0.6517	Remote Similarity	NPD6695	Phase 3
0.6512	Remote Similarity	NPD7145	Approved
0.6495	Remote Similarity	NPD4755	Approved
0.6489	Remote Similarity	NPD5693	Phase 1
0.6489	Remote Similarity	NPD5284	Approved
0.6489	Remote Similarity	NPD5281	Approved
0.6484	Remote Similarity	NPD7521	Approved
0.6484	Remote Similarity	NPD7334	Approved
0.6484	Remote Similarity	NPD5330	Approved
0.6484	Remote Similarity	NPD6409	Approved
0.6484	Remote Similarity	NPD4694	Approved
0.6484	Remote Similarity	NPD7146	Approved
0.6484	Remote Similarity	NPD5280	Approved
0.6484	Remote Similarity	NPD6684	Approved
0.6477	Remote Similarity	NPD6902	Approved
0.6465	Remote Similarity	NPD5223	Approved
0.6463	Remote Similarity	NPD4691	Approved
0.6452	Remote Similarity	NPD4753	Phase 2
0.6444	Remote Similarity	NPD3666	Approved
0.6444	Remote Similarity	NPD3668	Phase 3
0.6444	Remote Similarity	NPD3133	Approved
0.6444	Remote Similarity	NPD3665	Phase 1
0.6436	Remote Similarity	NPD5141	Approved
0.6429	Remote Similarity	NPD5733	Approved
0.6429	Remote Similarity	NPD4058	Approved
0.6429	Remote Similarity	NPD4687	Approved
0.6421	Remote Similarity	NPD6399	Phase 3
0.642	Remote Similarity	NPD3621	Clinical (unspecified phase)
0.64	Remote Similarity	NPD5225	Approved
0.64	Remote Similarity	NPD5226	Approved
0.64	Remote Similarity	NPD5224	Approved
0.64	Remote Similarity	NPD4633	Approved
0.6395	Remote Similarity	NPD5776	Phase 2
0.6395	Remote Similarity	NPD6925	Approved
0.6392	Remote Similarity	NPD5222	Approved
0.6392	Remote Similarity	NPD5221	Approved
0.6392	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6383	Remote Similarity	NPD5207	Approved
0.6374	Remote Similarity	NPD6893	Approved
0.6374	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD4700	Approved
0.6354	Remote Similarity	NPD5771	Approved
0.6353	Remote Similarity	NPD8264	Approved
0.6344	Remote Similarity	NPD6903	Approved
0.6337	Remote Similarity	NPD5174	Approved
0.6337	Remote Similarity	NPD5175	Approved
0.6327	Remote Similarity	NPD5173	Approved
0.6322	Remote Similarity	NPD3617	Approved
0.6316	Remote Similarity	NPD5694	Approved
0.6316	Remote Similarity	NPD6050	Approved
0.6292	Remote Similarity	NPD4692	Approved
0.6292	Remote Similarity	NPD4139	Approved
0.6289	Remote Similarity	NPD5210	Approved
0.6289	Remote Similarity	NPD4629	Approved
0.6263	Remote Similarity	NPD7638	Approved
0.625	Remote Similarity	NPD6881	Approved
0.625	Remote Similarity	NPD6683	Phase 2
0.625	Remote Similarity	NPD6899	Approved
0.6239	Remote Similarity	NPD7115	Discovery
0.6237	Remote Similarity	NPD7750	Discontinued
0.6237	Remote Similarity	NPD7524	Approved
0.6224	Remote Similarity	NPD4697	Phase 3
0.6214	Remote Similarity	NPD6675	Approved
0.6214	Remote Similarity	NPD7128	Approved
0.6214	Remote Similarity	NPD5739	Approved
0.6214	Remote Similarity	NPD6402	Approved
0.6211	Remote Similarity	NPD5692	Phase 3
0.62	Remote Similarity	NPD7640	Approved
0.62	Remote Similarity	NPD7639	Approved
0.619	Remote Similarity	NPD5276	Approved
0.6186	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6186	Remote Similarity	NPD7900	Approved
0.6186	Remote Similarity	NPD5707	Approved
0.6176	Remote Similarity	NPD4754	Approved
0.6162	Remote Similarity	NPD6084	Phase 2
0.6162	Remote Similarity	NPD6083	Phase 2
0.6161	Remote Similarity	NPD7503	Approved
0.6154	Remote Similarity	NPD4788	Approved
0.6154	Remote Similarity	NPD5697	Approved
0.6146	Remote Similarity	NPD8034	Phase 2
0.6146	Remote Similarity	NPD7515	Phase 2
0.6146	Remote Similarity	NPD8035	Phase 2
0.6145	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.6132	Remote Similarity	NPD7102	Approved
0.6132	Remote Similarity	NPD6883	Approved
0.6132	Remote Similarity	NPD7290	Approved
0.6129	Remote Similarity	NPD5279	Phase 3
0.6111	Remote Similarity	NPD6898	Phase 1
0.61	Remote Similarity	NPD5290	Discontinued
0.6095	Remote Similarity	NPD4729	Approved
0.6095	Remote Similarity	NPD6011	Approved
0.6095	Remote Similarity	NPD7320	Approved
0.6095	Remote Similarity	NPD4730	Approved
0.6076	Remote Similarity	NPD368	Approved
0.6075	Remote Similarity	NPD6617	Approved
0.6075	Remote Similarity	NPD6650	Approved
0.6075	Remote Similarity	NPD8130	Phase 1
0.6075	Remote Similarity	NPD6649	Approved
0.6075	Remote Similarity	NPD6869	Approved
0.6075	Remote Similarity	NPD6847	Approved
0.6071	Remote Similarity	NPD6939	Phase 2
0.6071	Remote Similarity	NPD6938	Clinical (unspecified phase)
0.6058	Remote Similarity	NPD6008	Approved
0.6058	Remote Similarity	NPD4767	Approved
0.6058	Remote Similarity	NPD4768	Approved
0.6042	Remote Similarity	NPD4096	Approved
0.6038	Remote Similarity	NPD6012	Approved
0.6038	Remote Similarity	NPD6014	Approved
0.6038	Remote Similarity	NPD6372	Approved
0.6038	Remote Similarity	NPD6013	Approved
0.6038	Remote Similarity	NPD6373	Approved
0.6024	Remote Similarity	NPD5360	Phase 3
0.6024	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.602	Remote Similarity	NPD7748	Approved
0.6019	Remote Similarity	NPD8297	Approved
0.6019	Remote Similarity	NPD6882	Approved
0.6	Remote Similarity	NPD4518	Approved
0.6	Remote Similarity	NPD7902	Approved
0.6	Remote Similarity	NPD5701	Approved
0.6	Remote Similarity	NPD4695	Discontinued
0.5981	Remote Similarity	NPD5251	Approved
0.5981	Remote Similarity	NPD5135	Approved
0.5981	Remote Similarity	NPD5249	Phase 3
0.5981	Remote Similarity	NPD5247	Approved
0.5981	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.5981	Remote Similarity	NPD4634	Approved
0.5981	Remote Similarity	NPD5169	Approved
0.5981	Remote Similarity	NPD5248	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